#------------------------------------------------------------------------------ #$Date: 2021-10-06 19:13:14 +0300 (Wed, 06 Oct 2021) $ #$Revision: 269772 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/82/7158295.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7158295 loop_ _publ_author_name 'Bormann, Carl Thomas' 'Fadaei-Tirani, Farzaneh' 'Scopelliti, Rosario' 'Severin, Kay' _publ_section_title ; Synthesis of bicyclic vinyl triazenes by Ficini-type reactions. ; _journal_issue 37 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 8113 _journal_page_last 8117 _journal_paper_doi 10.1039/d1ob01546j _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C20 H27 N3 O' _chemical_formula_sum 'C20 H27 N3 O' _chemical_formula_weight 325.44 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2021-01-05 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226) ; _audit_update_record ; 2021-08-03 deposited with the CCDC. 2021-09-02 downloaded from the CCDC. ; _cell_angle_alpha 69.946(8) _cell_angle_beta 72.758(6) _cell_angle_gamma 64.698(8) _cell_formula_units_Z 4 _cell_length_a 10.9301(7) _cell_length_b 12.0124(11) _cell_length_c 16.8138(12) _cell_measurement_reflns_used 5974 _cell_measurement_temperature 140.15 _cell_measurement_theta_max 72.6870 _cell_measurement_theta_min 4.9260 _cell_volume 1845.4(3) _computing_cell_refinement 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 140.15 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2817 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.971 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -31.00 -4.00 1.00 3.00 -- -40.91 70.00 133.00 27 2 \w -114.00 -10.00 1.00 3.00 -- -40.91 -70.00 1.00 104 3 \w 36.00 100.00 1.00 3.00 -- 40.91 70.00 133.00 64 4 \w -5.00 20.00 1.00 3.00 -- 40.91 -70.00 1.00 25 5 \w 91.00 124.00 1.00 12.00 -- 105.15 -70.00 1.00 33 6 \w 74.00 173.00 1.00 12.00 -- 105.15 70.00 133.00 99 7 \w -20.00 71.00 1.00 3.00 -- 40.91 -77.00-120.00 91 8 \w 26.00 111.00 1.00 3.00 -- 40.91 57.00 60.00 85 9 \w 17.00 51.00 1.00 3.00 -- 40.91 38.00 -90.00 34 10 \w 36.00 80.00 1.00 3.00 -- 40.91-125.00-180.00 44 11 \w 69.00 113.00 1.00 3.00 -- 40.91 38.00 -90.00 44 12 \w 30.00 107.00 1.00 12.00 -- 105.15-111.00 -90.00 77 13 \w 29.00 109.00 1.00 12.00 -- 105.15-111.00 0.00 80 14 \w 48.00 107.00 1.00 12.00 -- 105.15-111.00-180.00 59 15 \w 81.00 106.00 1.00 12.00 -- 105.15 -94.00 60.00 25 16 \w 25.00 63.00 1.00 12.00 -- 105.15 -94.00 60.00 38 17 \w 72.00 130.00 1.00 12.00 -- 105.15 178.00 -60.00 58 18 \w 153.00 178.00 1.00 12.00 -- 105.15 77.00-120.00 25 19 \w 105.00 165.00 1.00 12.00 -- 105.15 111.00 30.00 60 20 \w 30.00 101.00 1.00 12.00 -- 105.15 -94.00 30.00 71 21 \w 80.00 178.00 1.00 12.00 -- 105.15 45.00 90.00 98 22 \w 79.00 163.00 1.00 12.00 -- 105.15 30.00-150.00 84 23 \w 39.00 81.00 1.00 12.00 -- 105.15-111.00 -30.00 42 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0206574000 _diffrn_orient_matrix_UB_12 -0.1173709000 _diffrn_orient_matrix_UB_13 -0.0277573000 _diffrn_orient_matrix_UB_21 0.1197281000 _diffrn_orient_matrix_UB_22 0.0219442000 _diffrn_orient_matrix_UB_23 -0.0715465000 _diffrn_orient_matrix_UB_31 0.1016129000 _diffrn_orient_matrix_UB_32 -0.0849228000 _diffrn_orient_matrix_UB_33 0.0626901000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_unetI/netI 0.0220 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.971 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 7640 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.971 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.866 _diffrn_reflns_theta_min 2.842 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.572 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.453 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear pale colourless' _exptl_crystal_density_diffrn 1.171 _exptl_crystal_description prism _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.461 _exptl_crystal_size_mid 0.168 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.512 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.084 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 442 _refine_ls_number_reflns 7640 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0883 _refine_ls_R_factor_gt 0.0810 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1697P)^2^+0.9442P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2450 _refine_ls_wR_factor_ref 0.2503 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6257 _reflns_number_total 7640 _reflns_threshold_expression 'I > 2\s(I)' _twin_special_details ; Component 2 rotated by 179.3084\% around [-0.01 -0.32 0.95] (reciprocal) or [-0.01 -0.70 0.72] (direct) ; _cod_data_source_file d1ob01546j2.cif _cod_data_source_block cb590-2 _cod_depositor_comments 'Adding full bibliography for 7158295--7158296.cif.' _cod_database_code 7158295 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C20 H27 N3 O1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.935 _shelx_estimated_absorpt_t_min 0.778 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.628(3) 0.372(3) 2. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 3.a Ternary CH refined with riding coordinates: C1(H1), C4(H4), C8(H8), C12(H12), C21(H21), C24(H24), C28(H28), C32(H32) 3.b Secondary CH2 refined with riding coordinates: C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B) 3.c Aromatic/amide H refined with riding coordinates: C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40) 3.d Idealised Me refined as rotating group: C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C22(H22A, H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C) ; _shelx_res_file ; TITL CB590-2 in P-1 cb590-2.res created by SHELXL-2018/3 at 15:11:57 on 05-Jan-2021 CELL 1.54184 10.930095 12.012429 16.813845 69.9463 72.7583 64.6982 ZERR 4 0.000747 0.001116 0.001233 0.0075 0.0063 0.0078 LATT 1 SFAC C H N O UNIT 80 108 12 4 L.S. 10 PLAN 10 SIZE 0.461 0.168 0.12 TEMP -133 CONF BOND LIST 4 MORE -1 WPDB -2 fmap 2 acta MERG 0 REM REM REM WGHT 0.169700 0.944200 BASF 0.37224 FVAR 5.57318 O1 4 0.543235 0.043046 0.719718 11.00000 0.03515 0.03739 = 0.04260 -0.00297 -0.02136 -0.00751 N1 3 0.072222 0.272047 0.501476 11.00000 0.01641 0.04952 = 0.03721 -0.01761 -0.00790 -0.00746 N2 3 0.173705 0.243294 0.542017 11.00000 0.01656 0.03848 = 0.03563 -0.01151 -0.00809 -0.00631 N3 3 0.293832 0.218057 0.495392 11.00000 0.01744 0.03840 = 0.03523 -0.01046 -0.00804 -0.00659 C1 1 -0.060077 0.279634 0.558914 11.00000 0.01580 0.05313 = 0.04398 -0.01967 -0.00774 -0.00735 AFIX 13 H1 2 -0.127217 0.296991 0.522691 11.00000 -1.20000 AFIX 0 C2 1 -0.113560 0.390262 0.599469 11.00000 0.02969 0.06719 = 0.07105 -0.03625 0.00294 -0.01218 AFIX 137 H2A 2 -0.049405 0.376856 0.635001 11.00000 -1.50000 H2B 2 -0.203838 0.396229 0.635468 11.00000 -1.50000 H2C 2 -0.122045 0.469283 0.554181 11.00000 -1.50000 AFIX 0 C3 1 -0.052746 0.154823 0.626466 11.00000 0.03491 0.06874 = 0.05033 -0.01553 -0.00455 -0.02589 AFIX 137 H3A 2 -0.018400 0.085744 0.597899 11.00000 -1.50000 H3B 2 -0.144683 0.161990 0.660183 11.00000 -1.50000 H3C 2 0.009554 0.136565 0.664707 11.00000 -1.50000 AFIX 0 C4 1 0.099081 0.260773 0.412498 11.00000 0.02227 0.04529 = 0.03497 -0.01493 -0.01098 -0.00199 AFIX 13 H4 2 0.189781 0.269736 0.383655 11.00000 -1.20000 AFIX 0 C5 1 0.111410 0.130294 0.413093 11.00000 0.08660 0.04231 = 0.04657 -0.01815 -0.02434 0.00370 AFIX 137 H5A 2 0.177259 0.065238 0.449745 11.00000 -1.50000 H5B 2 0.143564 0.119278 0.354358 11.00000 -1.50000 H5C 2 0.021400 0.121763 0.435561 11.00000 -1.50000 AFIX 0 C6 1 -0.008885 0.367135 0.361683 11.00000 0.02796 0.04061 = 0.04556 -0.01060 -0.01574 -0.00682 AFIX 137 H6A 2 -0.097459 0.355759 0.384685 11.00000 -1.50000 H6B 2 0.018987 0.364818 0.301069 11.00000 -1.50000 H6C 2 -0.017718 0.449332 0.366566 11.00000 -1.50000 AFIX 0 C7 1 0.391613 0.197190 0.541815 11.00000 0.01867 0.03252 = 0.03425 -0.00787 -0.00888 -0.00770 C8 1 0.361218 0.193589 0.636734 11.00000 0.01987 0.03129 = 0.03422 -0.00761 -0.00927 -0.00569 AFIX 13 H8 2 0.296574 0.148723 0.672109 11.00000 -1.20000 AFIX 0 C9 1 0.317654 0.326969 0.650841 11.00000 0.02239 0.03364 = 0.04273 -0.01480 -0.00827 -0.00020 AFIX 23 H9A 2 0.221485 0.377553 0.642098 11.00000 -1.20000 H9B 2 0.322169 0.318414 0.710699 11.00000 -1.20000 AFIX 0 C10 1 0.411911 0.396170 0.588172 11.00000 0.03017 0.02785 = 0.04775 -0.00977 -0.01332 -0.00413 AFIX 23 H10A 2 0.394350 0.473019 0.605841 11.00000 -1.20000 H10B 2 0.389476 0.424128 0.529873 11.00000 -1.20000 AFIX 0 C11 1 0.564663 0.312195 0.584873 11.00000 0.02705 0.03479 = 0.04376 -0.00962 -0.01270 -0.01090 AFIX 23 H11A 2 0.593592 0.303552 0.637864 11.00000 -1.20000 H11B 2 0.619797 0.353531 0.535209 11.00000 -1.20000 AFIX 0 C12 1 0.593182 0.178011 0.576533 11.00000 0.01771 0.03337 = 0.04120 -0.01342 -0.01226 -0.00297 AFIX 13 H12 2 0.692998 0.123247 0.570731 11.00000 -1.20000 AFIX 0 C13 1 0.525205 0.183800 0.507057 11.00000 0.01984 0.03078 = 0.03628 -0.01014 -0.00959 -0.00616 C14 1 0.506305 0.122590 0.655666 11.00000 0.02377 0.02641 = 0.03875 -0.01101 -0.01509 -0.00228 C15 1 0.599518 0.176758 0.419845 11.00000 0.01835 0.03334 = 0.03715 -0.00961 -0.00624 -0.00594 C16 1 0.721111 0.204514 0.388974 11.00000 0.02421 0.05414 = 0.04256 -0.01687 -0.00381 -0.01544 AFIX 43 H16 2 0.751444 0.230690 0.424560 11.00000 -1.20000 AFIX 0 C17 1 0.796990 0.194310 0.307823 11.00000 0.02944 0.06212 = 0.04707 -0.01636 -0.00064 -0.02187 AFIX 43 H17 2 0.877822 0.214395 0.288294 11.00000 -1.20000 AFIX 0 C18 1 0.755960 0.155141 0.255097 11.00000 0.02998 0.04648 = 0.03732 -0.01292 -0.00084 -0.01048 AFIX 43 H18 2 0.808839 0.146971 0.199844 11.00000 -1.20000 AFIX 0 C19 1 0.636109 0.127786 0.283964 11.00000 0.03214 0.03512 = 0.03806 -0.01280 -0.00797 -0.00792 AFIX 43 H19 2 0.606806 0.101404 0.247970 11.00000 -1.20000 AFIX 0 C20 1 0.558900 0.138827 0.365223 11.00000 0.02333 0.03089 = 0.03994 -0.01134 -0.00700 -0.00634 AFIX 43 H20 2 0.477191 0.120222 0.383788 11.00000 -1.20000 AFIX 0 O2 4 -0.016268 0.103630 1.067166 11.00000 0.04013 0.04517 = 0.03689 -0.00792 -0.00474 -0.02070 N4 3 0.438218 0.336977 0.869325 11.00000 0.01728 0.03169 = 0.04870 -0.00598 -0.01378 -0.00568 N5 3 0.339755 0.289293 0.898254 11.00000 0.01866 0.03384 = 0.03582 -0.00731 -0.01077 -0.00815 N6 3 0.217747 0.371200 0.888660 11.00000 0.01648 0.03394 = 0.03500 -0.00917 -0.00770 -0.00707 C21 1 0.570596 0.246215 0.895689 11.00000 0.01740 0.03790 = 0.05000 -0.01005 -0.01455 -0.00571 AFIX 13 H21 2 0.636535 0.291995 0.873740 11.00000 -1.20000 AFIX 0 C22 1 0.557875 0.201667 0.992954 11.00000 0.03573 0.06647 = 0.05064 -0.01532 -0.02149 -0.00158 AFIX 137 H22A 2 0.517175 0.275686 1.017341 11.00000 -1.50000 H22B 2 0.649235 0.149625 1.008065 11.00000 -1.50000 H22C 2 0.499010 0.150960 1.016187 11.00000 -1.50000 AFIX 0 C23 1 0.629520 0.135187 0.855037 11.00000 0.03206 0.04397 = 0.06378 -0.02192 -0.02018 0.00175 AFIX 137 H23A 2 0.568674 0.086459 0.876814 11.00000 -1.50000 H23B 2 0.720716 0.080171 0.869552 11.00000 -1.50000 H23C 2 0.637325 0.167040 0.792425 11.00000 -1.50000 AFIX 0 C24 1 0.410666 0.473976 0.834749 11.00000 0.02390 0.03183 = 0.04407 -0.00755 -0.01170 -0.00691 AFIX 13 H24 2 0.321026 0.513451 0.813910 11.00000 -1.20000 AFIX 0 C25 1 0.393952 0.534615 0.905112 11.00000 0.07063 0.04161 = 0.04581 -0.01854 0.00481 -0.01739 AFIX 137 H25A 2 0.320544 0.518155 0.952140 11.00000 -1.50000 H25B 2 0.370184 0.626586 0.881585 11.00000 -1.50000 H25C 2 0.480358 0.498182 0.926953 11.00000 -1.50000 AFIX 0 C26 1 0.519403 0.500620 0.758118 11.00000 0.03079 0.03933 = 0.04146 -0.01246 -0.00764 -0.01111 AFIX 137 H26A 2 0.606625 0.471895 0.777524 11.00000 -1.50000 H26B 2 0.490053 0.592165 0.731174 11.00000 -1.50000 H26C 2 0.531650 0.454980 0.716241 11.00000 -1.50000 AFIX 0 C27 1 0.121306 0.312554 0.916741 11.00000 0.01925 0.03291 = 0.03090 -0.00875 -0.00889 -0.00828 C28 1 0.155681 0.169755 0.951055 11.00000 0.02165 0.03421 = 0.03224 -0.00766 -0.00883 -0.00878 AFIX 13 H28 2 0.226404 0.127742 0.989113 11.00000 -1.20000 AFIX 0 C29 1 0.189915 0.105345 0.877511 11.00000 0.02266 0.03497 = 0.03913 -0.01263 -0.00742 -0.00698 AFIX 23 H29A 2 0.282614 0.100648 0.844175 11.00000 -1.20000 H29B 2 0.190799 0.017474 0.902371 11.00000 -1.20000 AFIX 0 C30 1 0.083412 0.180323 0.817111 11.00000 0.02288 0.04561 = 0.03664 -0.01587 -0.00578 -0.01039 AFIX 23 H30A 2 0.101132 0.258011 0.780142 11.00000 -1.20000 H30B 2 0.095256 0.127696 0.779204 11.00000 -1.20000 AFIX 0 C31 1 -0.064848 0.218479 0.865314 11.00000 0.02182 0.04292 = 0.04019 -0.01372 -0.00809 -0.01126 AFIX 23 H31A 2 -0.091537 0.142782 0.889375 11.00000 -1.20000 H31B 2 -0.126839 0.281590 0.824711 11.00000 -1.20000 AFIX 0 C32 1 -0.081587 0.276269 0.939288 11.00000 0.01695 0.03900 = 0.03850 -0.01405 -0.00486 -0.00888 AFIX 13 H32 2 -0.178945 0.307511 0.969483 11.00000 -1.20000 AFIX 0 C33 1 -0.014277 0.375385 0.911119 11.00000 0.01915 0.03736 = 0.03165 -0.01136 -0.00604 -0.01004 C34 1 0.014209 0.171256 0.998392 11.00000 0.03059 0.03305 = 0.03539 -0.01131 -0.00596 -0.01425 C35 1 -0.089732 0.511684 0.881730 11.00000 0.01912 0.03620 = 0.03248 -0.01073 -0.00736 -0.00565 C36 1 -0.213130 0.553394 0.852262 11.00000 0.02100 0.04211 = 0.04582 -0.01286 -0.00991 -0.00772 AFIX 43 H36 2 -0.246245 0.492592 0.851281 11.00000 -1.20000 AFIX 0 C37 1 -0.287867 0.682315 0.824441 11.00000 0.02580 0.04722 = 0.05085 -0.01115 -0.01746 -0.00287 AFIX 43 H37 2 -0.370530 0.708552 0.803864 11.00000 -1.20000 AFIX 0 C38 1 -0.242899 0.772706 0.826467 11.00000 0.03316 0.03861 = 0.04207 -0.00883 -0.01459 0.00151 AFIX 43 H38 2 -0.294167 0.860758 0.807489 11.00000 -1.20000 AFIX 0 C39 1 -0.121387 0.732895 0.856716 11.00000 0.03420 0.03710 = 0.03972 -0.01154 -0.00843 -0.00805 AFIX 43 H39 2 -0.090095 0.794301 0.858778 11.00000 -1.20000 AFIX 0 C40 1 -0.045552 0.604112 0.883904 11.00000 0.02535 0.03828 = 0.03633 -0.01240 -0.01160 -0.00708 AFIX 43 H40 2 0.037218 0.578458 0.904201 11.00000 -1.20000 AFIX 0 HKLF 5 REM CB590-2 in P-1 REM wR2 = 0.2503, GooF = S = 1.048, Restrained GooF = 1.048 for all data REM R1 = 0.0810 for 6257 Fo > 4sig(Fo) and 0.0883 for all 7640 data REM 442 parameters refined using 0 restraints END WGHT 0.1697 0.9441 REM Highest difference peak 0.512, deepest hole -0.406, 1-sigma level 0.084 Q1 1 0.7478 0.2582 0.3320 11.00000 0.05 0.51 Q2 1 0.4734 0.4616 0.7841 11.00000 0.05 0.51 Q3 1 0.5436 0.1588 0.6207 11.00000 0.05 0.46 Q4 1 0.4375 0.3965 0.8390 11.00000 0.05 0.45 Q5 1 0.7910 0.1231 0.6104 11.00000 0.05 0.41 Q6 1 0.0051 0.1183 0.5963 11.00000 0.05 0.41 Q7 1 0.0616 0.3457 0.8827 11.00000 0.05 0.40 Q8 1 0.3703 0.3604 0.6291 11.00000 0.05 0.39 Q9 1 -0.2930 0.2842 1.0027 11.00000 0.05 0.39 Q10 1 0.4872 -0.0027 0.7593 11.00000 0.05 0.39 ; _shelx_res_checksum 43924 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.825 _oxdiff_exptl_absorpt_empirical_full_min 0.431 _oxdiff_twin_integration_method simultaneous _oxdiff_twin_items 2 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5432(2) 0.0430(2) 0.71972(15) 0.0390(5) Uani 1 1 d . . . . . N1 N 0.0722(2) 0.2720(3) 0.50148(17) 0.0334(6) Uani 1 1 d . . . . . N2 N 0.1737(2) 0.2433(2) 0.54202(16) 0.0301(5) Uani 1 1 d . . . . . N3 N 0.2938(2) 0.2181(2) 0.49539(17) 0.0305(5) Uani 1 1 d . . . . . C1 C -0.0601(3) 0.2796(3) 0.5589(2) 0.0368(7) Uani 1 1 d . . . . . H1 H -0.127217 0.296991 0.522691 0.044 Uiso 1 1 calc R U . . . C2 C -0.1136(4) 0.3903(4) 0.5995(3) 0.0554(10) Uani 1 1 d . . . . . H2A H -0.049405 0.376856 0.635001 0.083 Uiso 1 1 calc R U . . . H2B H -0.203838 0.396229 0.635468 0.083 Uiso 1 1 calc R U . . . H2C H -0.122045 0.469283 0.554181 0.083 Uiso 1 1 calc R U . . . C3 C -0.0527(4) 0.1548(4) 0.6265(3) 0.0493(9) Uani 1 1 d . . . . . H3A H -0.018400 0.085744 0.597899 0.074 Uiso 1 1 calc R U . . . H3B H -0.144683 0.161990 0.660183 0.074 Uiso 1 1 calc R U . . . H3C H 0.009554 0.136565 0.664707 0.074 Uiso 1 1 calc R U . . . C4 C 0.0991(3) 0.2608(3) 0.4125(2) 0.0351(7) Uani 1 1 d . . . . . H4 H 0.189781 0.269736 0.383655 0.042 Uiso 1 1 calc R U . . . C5 C 0.1114(5) 0.1303(4) 0.4131(3) 0.0634(12) Uani 1 1 d . . . . . H5A H 0.177259 0.065238 0.449745 0.095 Uiso 1 1 calc R U . . . H5B H 0.143564 0.119278 0.354358 0.095 Uiso 1 1 calc R U . . . H5C H 0.021400 0.121763 0.435561 0.095 Uiso 1 1 calc R U . . . C6 C -0.0089(3) 0.3671(3) 0.3617(2) 0.0379(7) Uani 1 1 d . . . . . H6A H -0.097459 0.355759 0.384685 0.057 Uiso 1 1 calc R U . . . H6B H 0.018987 0.364818 0.301069 0.057 Uiso 1 1 calc R U . . . H6C H -0.017718 0.449332 0.366566 0.057 Uiso 1 1 calc R U . . . C7 C 0.3916(3) 0.1972(3) 0.54181(19) 0.0282(6) Uani 1 1 d . . . . . C8 C 0.3612(3) 0.1936(3) 0.63673(19) 0.0289(6) Uani 1 1 d . . . . . H8 H 0.296574 0.148723 0.672109 0.035 Uiso 1 1 calc R U . . . C9 C 0.3177(3) 0.3270(3) 0.6508(2) 0.0345(7) Uani 1 1 d . . . . . H9A H 0.221485 0.377553 0.642098 0.041 Uiso 1 1 calc R U . . . H9B H 0.322169 0.318414 0.710699 0.041 Uiso 1 1 calc R U . . . C10 C 0.4119(3) 0.3962(3) 0.5882(2) 0.0360(7) Uani 1 1 d . . . . . H10A H 0.394350 0.473019 0.605841 0.043 Uiso 1 1 calc R U . . . H10B H 0.389476 0.424128 0.529873 0.043 Uiso 1 1 calc R U . . . C11 C 0.5647(3) 0.3122(3) 0.5849(2) 0.0338(6) Uani 1 1 d . . . . . H11A H 0.593592 0.303552 0.637864 0.041 Uiso 1 1 calc R U . . . H11B H 0.619797 0.353531 0.535209 0.041 Uiso 1 1 calc R U . . . C12 C 0.5932(3) 0.1780(3) 0.5765(2) 0.0302(6) Uani 1 1 d . . . . . H12 H 0.692998 0.123247 0.570731 0.036 Uiso 1 1 calc R U . . . C13 C 0.5252(3) 0.1838(3) 0.50706(19) 0.0285(6) Uani 1 1 d . . . . . C14 C 0.5063(3) 0.1226(3) 0.6557(2) 0.0290(6) Uani 1 1 d . . . . . C15 C 0.5995(3) 0.1768(3) 0.4198(2) 0.0303(6) Uani 1 1 d . . . . . C16 C 0.7211(3) 0.2045(3) 0.3890(2) 0.0390(7) Uani 1 1 d . . . . . H16 H 0.751444 0.230690 0.424560 0.047 Uiso 1 1 calc R U . . . C17 C 0.7970(4) 0.1943(4) 0.3078(2) 0.0450(8) Uani 1 1 d . . . . . H17 H 0.877822 0.214395 0.288294 0.054 Uiso 1 1 calc R U . . . C18 C 0.7560(3) 0.1551(3) 0.2551(2) 0.0397(7) Uani 1 1 d . . . . . H18 H 0.808839 0.146971 0.199844 0.048 Uiso 1 1 calc R U . . . C19 C 0.6361(3) 0.1278(3) 0.2840(2) 0.0352(6) Uani 1 1 d . . . . . H19 H 0.606806 0.101404 0.247970 0.042 Uiso 1 1 calc R U . . . C20 C 0.5589(3) 0.1388(3) 0.3652(2) 0.0316(6) Uani 1 1 d . . . . . H20 H 0.477191 0.120222 0.383788 0.038 Uiso 1 1 calc R U . . . O2 O -0.0163(2) 0.1036(2) 1.06717(15) 0.0400(5) Uani 1 1 d . . . . . N4 N 0.4382(2) 0.3370(2) 0.86932(18) 0.0330(6) Uani 1 1 d . . . . . N5 N 0.3398(2) 0.2893(2) 0.89825(16) 0.0289(5) Uani 1 1 d . . . . . N6 N 0.2177(2) 0.3712(2) 0.88866(16) 0.0283(5) Uani 1 1 d . . . . . C21 C 0.5706(3) 0.2462(3) 0.8957(2) 0.0349(7) Uani 1 1 d . . . . . H21 H 0.636535 0.291995 0.873740 0.042 Uiso 1 1 calc R U . . . C22 C 0.5579(4) 0.2017(4) 0.9930(3) 0.0536(10) Uani 1 1 d . . . . . H22A H 0.517175 0.275686 1.017341 0.080 Uiso 1 1 calc R U . . . H22B H 0.649235 0.149625 1.008065 0.080 Uiso 1 1 calc R U . . . H22C H 0.499010 0.150960 1.016187 0.080 Uiso 1 1 calc R U . . . C23 C 0.6295(4) 0.1352(3) 0.8550(3) 0.0471(9) Uani 1 1 d . . . . . H23A H 0.568674 0.086459 0.876814 0.071 Uiso 1 1 calc R U . . . H23B H 0.720716 0.080171 0.869552 0.071 Uiso 1 1 calc R U . . . H23C H 0.637325 0.167040 0.792425 0.071 Uiso 1 1 calc R U . . . C24 C 0.4107(3) 0.4740(3) 0.8347(2) 0.0336(6) Uani 1 1 d . . . . . H24 H 0.321026 0.513451 0.813910 0.040 Uiso 1 1 calc R U . . . C25 C 0.3940(5) 0.5346(4) 0.9051(3) 0.0552(10) Uani 1 1 d . . . . . H25A H 0.320544 0.518155 0.952140 0.083 Uiso 1 1 calc R U . . . H25B H 0.370184 0.626586 0.881585 0.083 Uiso 1 1 calc R U . . . H25C H 0.480358 0.498182 0.926953 0.083 Uiso 1 1 calc R U . . . C26 C 0.5194(3) 0.5006(3) 0.7581(2) 0.0368(7) Uani 1 1 d . . . . . H26A H 0.606625 0.471895 0.777524 0.055 Uiso 1 1 calc R U . . . H26B H 0.490053 0.592165 0.731174 0.055 Uiso 1 1 calc R U . . . H26C H 0.531650 0.454980 0.716241 0.055 Uiso 1 1 calc R U . . . C27 C 0.1213(3) 0.3126(3) 0.91674(18) 0.0268(6) Uani 1 1 d . . . . . C28 C 0.1557(3) 0.1698(3) 0.95106(19) 0.0291(6) Uani 1 1 d . . . . . H28 H 0.226404 0.127742 0.989113 0.035 Uiso 1 1 calc R U . . . C29 C 0.1899(3) 0.1053(3) 0.8775(2) 0.0321(6) Uani 1 1 d . . . . . H29A H 0.282614 0.100648 0.844175 0.039 Uiso 1 1 calc R U . . . H29B H 0.190799 0.017474 0.902371 0.039 Uiso 1 1 calc R U . . . C30 C 0.0834(3) 0.1803(3) 0.8171(2) 0.0341(6) Uani 1 1 d . . . . . H30A H 0.101132 0.258011 0.780142 0.041 Uiso 1 1 calc R U . . . H30B H 0.095256 0.127696 0.779204 0.041 Uiso 1 1 calc R U . . . C31 C -0.0648(3) 0.2185(3) 0.8653(2) 0.0336(6) Uani 1 1 d . . . . . H31A H -0.091537 0.142782 0.889375 0.040 Uiso 1 1 calc R U . . . H31B H -0.126839 0.281590 0.824711 0.040 Uiso 1 1 calc R U . . . C32 C -0.0816(3) 0.2763(3) 0.9393(2) 0.0307(6) Uani 1 1 d . . . . . H32 H -0.178945 0.307511 0.969483 0.037 Uiso 1 1 calc R U . . . C33 C -0.0143(3) 0.3754(3) 0.91112(18) 0.0283(6) Uani 1 1 d . . . . . C34 C 0.0142(3) 0.1713(3) 0.9984(2) 0.0312(6) Uani 1 1 d . . . . . C35 C -0.0897(3) 0.5117(3) 0.88173(19) 0.0296(6) Uani 1 1 d . . . . . C36 C -0.2131(3) 0.5534(3) 0.8523(2) 0.0362(7) Uani 1 1 d . . . . . H36 H -0.246245 0.492592 0.851281 0.043 Uiso 1 1 calc R U . . . C37 C -0.2879(3) 0.6823(3) 0.8244(2) 0.0428(8) Uani 1 1 d . . . . . H37 H -0.370530 0.708552 0.803864 0.051 Uiso 1 1 calc R U . . . C38 C -0.2429(3) 0.7727(3) 0.8265(2) 0.0417(7) Uani 1 1 d . . . . . H38 H -0.294167 0.860758 0.807489 0.050 Uiso 1 1 calc R U . . . C39 C -0.1214(3) 0.7329(3) 0.8567(2) 0.0378(7) Uani 1 1 d . . . . . H39 H -0.090095 0.794301 0.858778 0.045 Uiso 1 1 calc R U . . . C40 C -0.0456(3) 0.6041(3) 0.8839(2) 0.0326(6) Uani 1 1 d . . . . . H40 H 0.037218 0.578458 0.904201 0.039 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0352(12) 0.0374(11) 0.0426(12) -0.0030(9) -0.0214(10) -0.0075(9) N1 0.0164(11) 0.0495(14) 0.0372(14) -0.0176(11) -0.0079(10) -0.0075(10) N2 0.0166(11) 0.0385(13) 0.0356(13) -0.0115(10) -0.0081(9) -0.0063(9) N3 0.0174(10) 0.0384(13) 0.0352(13) -0.0105(10) -0.0080(10) -0.0066(9) C1 0.0158(12) 0.0531(18) 0.0440(17) -0.0197(14) -0.0077(12) -0.0074(12) C2 0.0297(17) 0.067(2) 0.071(3) -0.036(2) 0.0029(17) -0.0122(16) C3 0.0349(17) 0.069(2) 0.050(2) -0.0155(18) -0.0046(15) -0.0259(17) C4 0.0223(13) 0.0453(16) 0.0350(15) -0.0149(13) -0.0110(12) -0.0020(12) C5 0.087(3) 0.0423(19) 0.047(2) -0.0182(17) -0.024(2) 0.004(2) C6 0.0280(14) 0.0406(16) 0.0456(18) -0.0106(14) -0.0157(13) -0.0068(12) C7 0.0187(12) 0.0325(13) 0.0342(15) -0.0079(11) -0.0089(11) -0.0077(10) C8 0.0199(12) 0.0313(13) 0.0342(15) -0.0076(11) -0.0093(11) -0.0057(10) C9 0.0224(13) 0.0336(15) 0.0427(16) -0.0148(12) -0.0083(12) -0.0002(11) C10 0.0302(15) 0.0279(14) 0.0478(18) -0.0098(12) -0.0133(13) -0.0041(11) C11 0.0270(14) 0.0348(15) 0.0438(17) -0.0096(12) -0.0127(13) -0.0109(12) C12 0.0177(12) 0.0334(14) 0.0412(16) -0.0134(12) -0.0123(11) -0.0030(10) C13 0.0198(12) 0.0308(13) 0.0363(15) -0.0101(11) -0.0096(11) -0.0062(10) C14 0.0238(13) 0.0264(13) 0.0387(15) -0.0110(11) -0.0151(12) -0.0023(10) C15 0.0184(12) 0.0333(14) 0.0371(15) -0.0096(11) -0.0062(11) -0.0059(10) C16 0.0242(14) 0.0541(19) 0.0426(17) -0.0169(14) -0.0038(13) -0.0154(13) C17 0.0294(15) 0.062(2) 0.0471(19) -0.0164(16) -0.0006(14) -0.0219(15) C18 0.0300(15) 0.0465(17) 0.0373(16) -0.0129(14) -0.0008(13) -0.0105(13) C19 0.0321(15) 0.0351(15) 0.0381(16) -0.0128(12) -0.0080(13) -0.0079(12) C20 0.0233(13) 0.0309(14) 0.0399(16) -0.0113(12) -0.0070(12) -0.0063(11) O2 0.0401(12) 0.0452(12) 0.0369(12) -0.0079(10) -0.0047(10) -0.0207(10) N4 0.0173(11) 0.0317(12) 0.0487(15) -0.0060(11) -0.0138(10) -0.0057(9) N5 0.0187(11) 0.0338(12) 0.0358(13) -0.0073(10) -0.0108(9) -0.0082(9) N6 0.0165(10) 0.0339(12) 0.0350(12) -0.0092(10) -0.0077(9) -0.0071(9) C21 0.0174(13) 0.0379(15) 0.0500(18) -0.0101(13) -0.0145(12) -0.0057(11) C22 0.0357(18) 0.066(2) 0.051(2) -0.0153(18) -0.0215(16) -0.0016(16) C23 0.0321(16) 0.0440(18) 0.064(2) -0.0219(16) -0.0202(16) 0.0018(14) C24 0.0239(13) 0.0318(14) 0.0441(17) -0.0075(12) -0.0117(12) -0.0069(11) C25 0.071(3) 0.0416(18) 0.046(2) -0.0185(15) 0.0048(18) -0.0174(18) C26 0.0308(15) 0.0393(16) 0.0415(17) -0.0125(13) -0.0076(13) -0.0111(12) C27 0.0192(12) 0.0329(14) 0.0309(14) -0.0088(11) -0.0089(10) -0.0083(10) C28 0.0217(13) 0.0342(14) 0.0322(14) -0.0077(11) -0.0088(11) -0.0088(11) C29 0.0227(13) 0.0350(14) 0.0391(16) -0.0126(12) -0.0074(12) -0.0070(11) C30 0.0229(13) 0.0456(16) 0.0366(15) -0.0159(13) -0.0058(12) -0.0104(12) C31 0.0218(13) 0.0429(16) 0.0402(16) -0.0137(13) -0.0081(12) -0.0113(12) C32 0.0169(12) 0.0390(15) 0.0385(15) -0.0140(12) -0.0049(11) -0.0089(11) C33 0.0191(12) 0.0374(14) 0.0316(14) -0.0114(11) -0.0060(11) -0.0100(11) C34 0.0306(14) 0.0331(14) 0.0354(15) -0.0113(12) -0.0060(12) -0.0142(12) C35 0.0191(12) 0.0362(15) 0.0325(14) -0.0107(11) -0.0074(11) -0.0056(11) C36 0.0210(13) 0.0421(16) 0.0458(18) -0.0129(14) -0.0099(12) -0.0077(12) C37 0.0258(14) 0.0472(18) 0.0509(19) -0.0112(15) -0.0175(14) -0.0029(13) C38 0.0332(16) 0.0386(16) 0.0421(17) -0.0088(13) -0.0146(14) 0.0015(13) C39 0.0342(16) 0.0371(15) 0.0397(16) -0.0115(13) -0.0084(13) -0.0080(12) C40 0.0253(13) 0.0383(15) 0.0363(15) -0.0124(12) -0.0116(12) -0.0071(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -2 -1 -1 0.2671 0 1 -1 0.0619 -2 -1 -2 0.2646 -2 -2 -1 0.2536 2 2 1 0.1538 0 2 -1 0.0632 -1 -1 -1 0.2630 3 5 5 0.1167 0 -1 -1 0.0978 0 1 1 0.0653 1 3 5 0.0861 0 3 5 0.0581 -2 5 5 0.1112 1 2 5 0.0970 0 0 1 0.0727 -5 1 -3 0.2057 -5 2 5 0.1700 -5 -3 5 0.1787 5 3 -5 0.1445 0 -5 1 0.0513 3 -2 -5 0.1282 5 -2 2 0.1692 0 -1 -5 0.0943 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C1 113.8(2) . . ? N2 N1 C4 121.9(2) . . ? C1 N1 C4 122.1(2) . . ? N3 N2 N1 114.9(2) . . ? N2 N3 C7 110.6(2) . . ? N1 C1 C2 110.6(3) . . ? N1 C1 C3 112.3(3) . . ? C2 C1 C3 111.8(3) . . ? N1 C4 C5 110.3(3) . . ? N1 C4 C6 111.4(2) . . ? C5 C4 C6 112.5(3) . . ? N3 C7 C8 124.4(2) . . ? C13 C7 N3 124.4(3) . . ? C13 C7 C8 111.1(2) . . ? C7 C8 C9 111.8(2) . . ? C14 C8 C7 98.9(2) . . ? C14 C8 C9 105.2(2) . . ? C10 C9 C8 110.7(2) . . ? C9 C10 C11 112.5(2) . . ? C10 C11 C12 111.5(2) . . ? C13 C12 C11 112.4(2) . . ? C14 C12 C11 105.1(2) . . ? C14 C12 C13 99.4(2) . . ? C7 C13 C12 108.0(3) . . ? C7 C13 C15 129.6(3) . . ? C15 C13 C12 122.3(2) . . ? O1 C14 C8 128.0(3) . . ? O1 C14 C12 128.2(3) . . ? C12 C14 C8 103.7(2) . . ? C16 C15 C13 119.7(3) . . ? C20 C15 C13 122.9(3) . . ? C20 C15 C16 117.3(3) . . ? C17 C16 C15 121.3(3) . . ? C18 C17 C16 120.5(3) . . ? C17 C18 C19 119.2(3) . . ? C18 C19 C20 120.5(3) . . ? C19 C20 C15 121.2(3) . . ? N5 N4 C21 113.3(2) . . ? N5 N4 C24 122.8(2) . . ? C24 N4 C21 122.0(2) . . ? N6 N5 N4 115.0(2) . . ? N5 N6 C27 111.4(2) . . ? N4 C21 C22 111.8(3) . . ? N4 C21 C23 111.0(3) . . ? C23 C21 C22 111.5(3) . . ? N4 C24 C25 110.7(3) . . ? N4 C24 C26 111.9(3) . . ? C26 C24 C25 112.1(3) . . ? N6 C27 C28 124.5(2) . . ? C33 C27 N6 123.9(3) . . ? C33 C27 C28 111.4(2) . . ? C27 C28 C29 111.3(2) . . ? C34 C28 C27 98.6(2) . . ? C34 C28 C29 105.5(2) . . ? C30 C29 C28 110.9(2) . . ? C31 C30 C29 113.1(3) . . ? C30 C31 C32 111.1(2) . . ? C33 C32 C31 112.8(2) . . ? C34 C32 C31 105.0(2) . . ? C34 C32 C33 99.6(2) . . ? C27 C33 C32 107.8(2) . . ? C27 C33 C35 129.3(3) . . ? C35 C33 C32 122.8(2) . . ? O2 C34 C28 128.2(3) . . ? O2 C34 C32 127.7(3) . . ? C28 C34 C32 104.0(2) . . ? C36 C35 C33 119.6(3) . . ? C40 C35 C33 122.5(2) . . ? C40 C35 C36 117.9(3) . . ? C37 C36 C35 121.1(3) . . ? C38 C37 C36 120.6(3) . . ? C37 C38 C39 119.1(3) . . ? C40 C39 C38 120.6(3) . . ? C39 C40 C35 120.8(3) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C14 1.208(4) . ? N1 N2 1.332(3) . ? N1 C1 1.467(4) . ? N1 C4 1.479(4) . ? N2 N3 1.282(3) . ? N3 C7 1.395(4) . ? C1 C2 1.515(5) . ? C1 C3 1.526(5) . ? C4 C5 1.511(5) . ? C4 C6 1.522(4) . ? C7 C8 1.520(4) . ? C7 C13 1.363(4) . ? C8 C9 1.546(4) . ? C8 C14 1.517(3) . ? C9 C10 1.533(5) . ? C10 C11 1.534(4) . ? C11 C12 1.554(4) . ? C12 C13 1.528(4) . ? C12 C14 1.516(4) . ? C13 C15 1.462(4) . ? C15 C16 1.414(4) . ? C15 C20 1.396(4) . ? C16 C17 1.386(5) . ? C17 C18 1.382(5) . ? C18 C19 1.393(5) . ? C19 C20 1.393(5) . ? O2 C34 1.211(4) . ? N4 N5 1.322(3) . ? N4 C21 1.476(3) . ? N4 C24 1.470(4) . ? N5 N6 1.292(3) . ? N6 C27 1.394(4) . ? C21 C22 1.519(5) . ? C21 C23 1.514(5) . ? C24 C25 1.521(5) . ? C24 C26 1.520(5) . ? C27 C28 1.522(4) . ? C27 C33 1.361(4) . ? C28 C29 1.550(4) . ? C28 C34 1.510(4) . ? C29 C30 1.541(4) . ? C30 C31 1.528(4) . ? C31 C32 1.553(4) . ? C32 C33 1.529(4) . ? C32 C34 1.518(4) . ? C33 C35 1.462(4) . ? C35 C36 1.401(4) . ? C35 C40 1.401(4) . ? C36 C37 1.390(5) . ? C37 C38 1.383(5) . ? C38 C39 1.394(5) . ? C39 C40 1.390(4) . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 N2 N3 C7 176.2(2) . . . . ? N2 N1 C1 C2 66.2(4) . . . . ? N2 N1 C1 C3 -59.5(4) . . . . ? N2 N1 C4 C5 91.1(4) . . . . ? N2 N1 C4 C6 -143.2(3) . . . . ? N2 N3 C7 C8 4.9(4) . . . . ? N2 N3 C7 C13 -171.6(3) . . . . ? N3 C7 C8 C9 -89.2(3) . . . . ? N3 C7 C8 C14 160.4(3) . . . . ? N3 C7 C13 C12 173.6(3) . . . . ? N3 C7 C13 C15 -5.8(5) . . . . ? C1 N1 N2 N3 170.4(3) . . . . ? C1 N1 C4 C5 -71.1(4) . . . . ? C1 N1 C4 C6 54.6(4) . . . . ? C4 N1 N2 N3 6.8(4) . . . . ? C4 N1 C1 C2 -130.2(3) . . . . ? C4 N1 C1 C3 104.1(3) . . . . ? C7 C8 C9 C10 -44.6(3) . . . . ? C7 C8 C14 O1 -142.0(3) . . . . ? C7 C8 C14 C12 39.8(3) . . . . ? C7 C13 C15 C16 159.2(3) . . . . ? C7 C13 C15 C20 -23.2(5) . . . . ? C8 C7 C13 C12 -3.4(3) . . . . ? C8 C7 C13 C15 177.3(3) . . . . ? C8 C9 C10 C11 -47.6(3) . . . . ? C9 C8 C14 O1 102.4(3) . . . . ? C9 C8 C14 C12 -75.9(3) . . . . ? C9 C10 C11 C12 46.8(4) . . . . ? C10 C11 C12 C13 47.3(4) . . . . ? C10 C11 C12 C14 -59.8(3) . . . . ? C11 C12 C13 C7 -82.7(3) . . . . ? C11 C12 C13 C15 96.7(3) . . . . ? C11 C12 C14 O1 -103.8(3) . . . . ? C11 C12 C14 C8 74.4(3) . . . . ? C12 C13 C15 C16 -20.0(4) . . . . ? C12 C13 C15 C20 157.5(3) . . . . ? C13 C7 C8 C9 87.7(3) . . . . ? C13 C7 C8 C14 -22.7(3) . . . . ? C13 C12 C14 O1 139.7(3) . . . . ? C13 C12 C14 C8 -42.0(3) . . . . ? C13 C15 C16 C17 177.6(3) . . . . ? C13 C15 C20 C19 -177.0(3) . . . . ? C14 C8 C9 C10 61.8(3) . . . . ? C14 C12 C13 C7 28.0(3) . . . . ? C14 C12 C13 C15 -152.6(3) . . . . ? C15 C16 C17 C18 -0.7(6) . . . . ? C16 C15 C20 C19 0.6(4) . . . . ? C16 C17 C18 C19 1.0(5) . . . . ? C17 C18 C19 C20 -0.5(5) . . . . ? C18 C19 C20 C15 -0.3(5) . . . . ? C20 C15 C16 C17 -0.1(5) . . . . ? N4 N5 N6 C27 177.0(2) . . . . ? N5 N4 C21 C22 -59.3(4) . . . . ? N5 N4 C21 C23 65.9(4) . . . . ? N5 N4 C24 C25 92.3(4) . . . . ? N5 N4 C24 C26 -141.9(3) . . . . ? N5 N6 C27 C28 -2.3(4) . . . . ? N5 N6 C27 C33 -177.4(3) . . . . ? N6 C27 C28 C29 -89.0(3) . . . . ? N6 C27 C28 C34 160.6(3) . . . . ? N6 C27 C33 C32 173.8(3) . . . . ? N6 C27 C33 C35 -4.3(5) . . . . ? C21 N4 N5 N6 169.2(3) . . . . ? C21 N4 C24 C25 -71.1(4) . . . . ? C21 N4 C24 C26 54.7(4) . . . . ? C24 N4 N5 N6 4.4(4) . . . . ? C24 N4 C21 C22 105.6(4) . . . . ? C24 N4 C21 C23 -129.2(3) . . . . ? C27 C28 C29 C30 -46.2(3) . . . . ? C27 C28 C34 O2 -140.8(3) . . . . ? C27 C28 C34 C32 39.9(3) . . . . ? C27 C33 C35 C36 157.5(3) . . . . ? C27 C33 C35 C40 -24.4(5) . . . . ? C28 C27 C33 C32 -1.8(3) . . . . ? C28 C27 C33 C35 180.0(3) . . . . ? C28 C29 C30 C31 -46.1(3) . . . . ? C29 C28 C34 O2 104.1(3) . . . . ? C29 C28 C34 C32 -75.1(3) . . . . ? C29 C30 C31 C32 46.7(4) . . . . ? C30 C31 C32 C33 46.8(3) . . . . ? C30 C31 C32 C34 -60.6(3) . . . . ? C31 C32 C33 C27 -84.2(3) . . . . ? C31 C32 C33 C35 94.1(3) . . . . ? C31 C32 C34 O2 -103.9(3) . . . . ? C31 C32 C34 C28 75.3(3) . . . . ? C32 C33 C35 C36 -20.5(4) . . . . ? C32 C33 C35 C40 157.7(3) . . . . ? C33 C27 C28 C29 86.6(3) . . . . ? C33 C27 C28 C34 -23.8(3) . . . . ? C33 C32 C34 O2 139.2(3) . . . . ? C33 C32 C34 C28 -41.5(3) . . . . ? C33 C35 C36 C37 179.5(3) . . . . ? C33 C35 C40 C39 -178.9(3) . . . . ? C34 C28 C29 C30 59.7(3) . . . . ? C34 C32 C33 C27 26.6(3) . . . . ? C34 C32 C33 C35 -155.1(3) . . . . ? C35 C36 C37 C38 -1.0(5) . . . . ? C36 C35 C40 C39 -0.7(5) . . . . ? C36 C37 C38 C39 0.1(5) . . . . ? C37 C38 C39 C40 0.5(5) . . . . ? C38 C39 C40 C35 -0.2(5) . . . . ? C40 C35 C36 C37 1.3(5) . . . . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined _oxdiff_twin_reflns_isolated _oxdiff_twin_reflns_overlapped _twin_individual_twin_lattice_type _twin_individual_twin_matrix_11 _twin_individual_twin_matrix_12 _twin_individual_twin_matrix_13 _twin_individual_twin_matrix_21 _twin_individual_twin_matrix_22 _twin_individual_twin_matrix_23 _twin_individual_twin_matrix_31 _twin_individual_twin_matrix_32 _twin_individual_twin_matrix_33 1 0.628(3) 9972 4910 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000 2 0.372(3) 0 4910 nmt -0.9943 -0.0040 -0.0107 0.0190 -0.5175 -0.5021 -0.0014 -1.4798 0.5128 loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -2.0010 -0.9970 -0.9998 0.1034 -0.1899 -0.1813 0.0019 0.9995 -1.0009 -0.0895 0.0938 -0.1474 -2.0007 -0.9979 -2.0008 0.1313 -0.1183 -0.2440 -2.0026 -1.9974 -0.9999 0.2208 -0.2121 -0.0966 2.0026 1.9974 0.9999 -0.2208 0.2121 0.0966 0.0036 1.9998 -1.0008 -0.2069 0.1159 -0.2322 -1.0012 -0.9991 -1.0004 0.1244 -0.0702 -0.0796 3.0062 4.9998 5.0035 -0.6636 0.1117 0.1945 -0.0013 -1.0012 -1.0011 0.1453 0.0495 0.0221 0.0013 1.0012 1.0011 -0.1453 -0.0495 -0.0221 1.0032 3.0033 5.0045 -0.4707 -0.1720 0.1606 0.0034 3.0054 5.0052 -0.4916 -0.2917 0.0589 -1.9929 5.0104 5.0066 -0.7682 -0.4869 -0.3141 1.0016 2.0029 5.0044 -0.3533 -0.1942 0.2454 -0.0003 0.0009 1.0010 -0.0279 -0.0716 0.0626 -4.9966 1.0083 -2.9997 -0.1383 -0.3615 -0.7814 -4.9973 2.0156 5.0082 -0.4788 -0.9124 -0.3650 -5.0055 -2.9861 5.0077 0.1081 -1.0231 0.0589 5.0055 2.9861 -5.0077 -0.1081 1.0231 -0.0589 -0.0085 -5.0009 1.0005 0.5590 -0.1823 0.4865 2.9977 -2.0114 -5.0070 0.4370 0.6730 0.1615 4.9952 -2.0095 1.9986 0.2836 0.4110 0.8035 -0.0001 -1.0047 -5.0050 0.2568 0.3360 -0.2285