#------------------------------------------------------------------------------ #$Date: 2022-11-25 02:27:43 +0200 (Fri, 25 Nov 2022) $ #$Revision: 279553 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/59/7245915.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_7245915 loop_ _publ_author_name 'Qian, Hang' 'Wang, Cui-Cui' 'Shen, Zi-Chen' 'Sun, Ming-Xue' 'Zhang, Hong-Chao' 'Fan, Shiming' 'Feng, Juan' 'Liu, Shouxin' 'Zhang, Zhi-Wei' _publ_section_title ; Catalyst- and additive-free [3+3] cyclization--aromatization of ,\g-dioxobutanoate with amines for synthesis of p-aminophenols ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D2GC03936B _journal_year 2022 _chemical_formula_moiety 'C23 H26 N2 O6' _chemical_formula_sum 'C23 H26 N2 O6' _chemical_formula_weight 426.46 _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 _audit_creation_date 2021-10-10 _audit_creation_method ; Olex2 1.3-ac4 (compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739) ; _audit_update_record ; 2022-09-27 deposited with the CCDC. 2022-11-24 downloaded from the CCDC. ; _cell_angle_alpha 112.233(6) _cell_angle_beta 90.786(5) _cell_angle_gamma 95.430(4) _cell_formula_units_Z 2 _cell_length_a 8.6271(4) _cell_length_b 11.5365(6) _cell_length_c 12.0186(8) _cell_measurement_reflns_used 1934 _cell_measurement_temperature 292.8(2) _cell_measurement_theta_max 75.1880 _cell_measurement_theta_min 3.9450 _cell_volume 1100.68(12) _computing_cell_refinement 'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment air _diffrn_ambient_temperature 292.8(2) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.941 _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 -98.00 -60.00 1.00 0.20 -- -47.57 142.00-123.00 38 2 \w -95.00 -29.00 1.00 0.20 -- -47.57 127.00 66.00 66 3 \w 38.00 112.00 1.00 0.20 -- 47.57 77.00 60.00 74 4 \w 98.00 154.00 1.00 0.61 -- 107.75 57.00 -30.00 56 5 \w 127.00 171.00 1.00 0.61 -- 107.75 37.00-120.00 44 6 \w -65.00 -28.00 1.00 0.61 -- -100.00 57.00 60.00 37 7 \w -102.00 -28.00 1.00 0.61 -- -100.00 77.00 -30.00 74 8 \w 41.00 67.00 1.00 0.20 -- 47.57-142.00-179.00 26 9 \w 55.00 80.00 1.00 0.61 -- 107.75-142.00-179.00 25 10 \w 38.00 107.00 1.00 0.61 -- 107.75-125.00-180.00 69 11 \w 73.00 102.00 1.00 0.61 -- 107.75 -99.00-150.00 29 12 \w 74.00 100.00 1.00 0.61 -- 107.75 -99.00-120.00 26 13 \w 68.00 94.00 1.00 0.61 -- 107.75-127.00 -9.00 26 14 \w 39.00 65.00 1.00 0.61 -- 107.75 -99.00-120.00 26 15 \w 33.00 58.00 1.00 0.20 -- 47.57-127.00 -9.00 25 16 \w 66.00 92.00 1.00 0.61 -- 107.75 -99.00 0.00 26 17 \w 62.00 88.00 1.00 0.61 -- 107.75 -77.00 0.00 26 18 \w 35.00 60.00 1.00 0.61 -- 107.75 -57.00 30.00 25 19 \w 36.00 62.00 1.00 0.61 -- 107.75 -57.00 60.00 26 20 \w 35.00 61.00 1.00 0.61 -- 107.75 -57.00 120.00 26 21 \w -26.00 19.00 1.00 0.20 -- 47.57 -19.00 90.00 45 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'ROD, Synergy Custom system, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0470618000 _diffrn_orient_matrix_UB_12 0.0058675000 _diffrn_orient_matrix_UB_13 -0.1217407000 _diffrn_orient_matrix_UB_21 0.0480764000 _diffrn_orient_matrix_UB_22 -0.1332692000 _diffrn_orient_matrix_UB_23 -0.0660069000 _diffrn_orient_matrix_UB_31 -0.1666048000 _diffrn_orient_matrix_UB_32 -0.0570099000 _diffrn_orient_matrix_UB_33 0.0073104000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_unetI/netI 0.0429 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.941 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 13568 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.941 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.434 _diffrn_reflns_theta_min 3.979 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.773 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90305 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear dark yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.287 _exptl_crystal_description plate _exptl_crystal_F_000 452 _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.525 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.037 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 284 _refine_ls_number_reflns 4395 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0624 _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^)+(0.0838P)^2^+0.2581P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1739 _refine_ls_wR_factor_ref 0.1903 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3095 _reflns_number_total 4395 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d2gc03936b2.cif _cod_data_source_block zhzhw_1010_auto _cod_database_code 7245915 _shelx_shelxl_version_number 2018/3 _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 0.992 _shelx_estimated_absorpt_t_min 0.941 _reflns_odcompleteness_completeness 76.92 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B) 2.b Aromatic/amide H refined with riding coordinates: N1(H1), N2(H2), C3(H3A), C6(H6), C17(H17), C19(H19), C20(H20), C22(H22) 2.c Idealised Me refined as rotating group: C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C23(H23A,H23B,H23C) 2.d Idealised tetrahedral OH refined as rotating group: O3(H3) ; _shelx_res_file ; TITL zhzhw_1010_auto_a.res in P-1 zhzhw_1010_auto.res created by SHELXL-2018/3 at 16:09:10 on 10-Oct-2021 REM Old TITL zhzhw_1010_auto in P-1 REM SHELXT solution in P-1: R1 0.237, Rweak 0.012, Alpha 0.074 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C22 N6 O3 CELL 1.54184 8.627113 11.536521 12.018568 112.233 90.7857 95.4303 ZERR 2 0.000432 0.000648 0.000824 0.0059 0.0048 0.0043 LATT 1 SFAC C H N O UNIT 46 52 4 12 L.S. 10 PLAN 1 SIZE 0.01 0.04 0.08 TEMP 19.7(2) BOND list 4 fmap 2 53 ACTA REM REM REM WGHT 0.083800 0.258100 FVAR 6.71692 O1 4 1.055421 0.768871 0.427067 11.00000 0.11579 0.08815 = 0.07961 0.02353 0.02154 -0.02884 O2 4 1.036915 0.600765 0.259819 11.00000 0.10695 0.09573 = 0.06570 0.02621 0.02953 -0.00532 O3 4 0.718361 0.260529 0.322307 11.00000 0.11292 0.05763 = 0.05706 0.00708 0.01139 -0.00454 AFIX 147 H3 2 0.651326 0.228324 0.352592 11.00000 -1.50000 AFIX 0 O4 4 0.543884 0.251432 0.497013 11.00000 0.08705 0.05521 = 0.07517 0.01500 0.00920 -0.00723 O5 4 0.537974 0.426215 0.661507 11.00000 0.07910 0.06052 = 0.05908 0.02321 0.00970 -0.00366 O6 4 0.235201 1.098333 0.725637 11.00000 0.08526 0.11437 = 0.13487 0.05379 0.00590 -0.00110 N1 3 0.872635 0.767936 0.604120 11.00000 0.08208 0.05313 = 0.06977 0.01148 0.02395 -0.00560 AFIX 43 H1 2 0.941949 0.810045 0.579515 11.00000 -1.20000 AFIX 0 N2 3 0.706914 1.151923 1.055760 11.00000 0.14676 0.06615 = 0.05215 0.01131 0.01351 0.00385 AFIX 43 H2 2 0.716348 1.188412 1.132907 11.00000 -1.20000 AFIX 0 C1 1 0.836067 0.642585 0.535513 11.00000 0.05938 0.05363 = 0.05695 0.01782 0.00337 0.00361 C2 1 0.898502 0.584831 0.421309 11.00000 0.05725 0.06276 = 0.05491 0.02218 0.00707 0.00804 C3 1 0.857284 0.457724 0.354486 11.00000 0.07170 0.06555 = 0.04931 0.01859 0.00946 0.01135 AFIX 43 H3A 2 0.899929 0.420478 0.280246 11.00000 -1.20000 AFIX 0 C4 1 0.754575 0.384782 0.395101 11.00000 0.07110 0.05336 = 0.05065 0.01403 0.00039 0.00446 C5 1 0.692354 0.440058 0.506927 11.00000 0.05907 0.05255 = 0.05109 0.01735 0.00062 0.00394 C6 1 0.733898 0.567334 0.575690 11.00000 0.06283 0.05475 = 0.05147 0.01561 0.00906 0.00531 AFIX 43 H6 2 0.692320 0.603199 0.650568 11.00000 -1.20000 AFIX 0 C7 1 1.003674 0.661238 0.372178 11.00000 0.06658 0.07609 = 0.06269 0.02949 0.00832 0.00555 C8 1 1.132376 0.676256 0.206183 11.00000 0.12679 0.11980 = 0.09045 0.04255 0.04184 -0.01489 AFIX 23 H8A 2 1.071759 0.738402 0.195697 11.00000 -1.20000 H8B 2 1.222211 0.720623 0.259931 11.00000 -1.20000 AFIX 0 C9 1 1.181689 0.600838 0.096611 11.00000 0.19871 0.15395 = 0.11275 0.02512 0.05865 -0.05147 AFIX 137 H9A 2 1.097460 0.578279 0.036745 11.00000 -1.50000 H9B 2 1.214676 0.525925 0.102117 11.00000 -1.50000 H9C 2 1.267360 0.645656 0.074468 11.00000 -1.50000 AFIX 0 C10 1 0.585506 0.362881 0.552831 11.00000 0.06343 0.05415 = 0.05667 0.01906 0.00086 0.00217 C11 1 0.434011 0.356209 0.714133 11.00000 0.07248 0.07468 = 0.07376 0.03655 0.00815 -0.00283 AFIX 23 H11A 2 0.486109 0.290286 0.725521 11.00000 -1.20000 H11B 2 0.341487 0.317637 0.661529 11.00000 -1.20000 AFIX 0 C12 1 0.390420 0.447973 0.832876 11.00000 0.10420 0.10528 = 0.07245 0.03979 0.02164 0.00577 AFIX 137 H12A 2 0.333830 0.509993 0.820046 11.00000 -1.50000 H12B 2 0.483221 0.488752 0.882534 11.00000 -1.50000 H12C 2 0.326285 0.403962 0.872119 11.00000 -1.50000 AFIX 0 C13 1 0.801784 0.832990 0.714782 11.00000 0.07987 0.05586 = 0.06090 0.01321 0.01339 -0.00140 AFIX 23 H13A 2 0.832643 0.801541 0.775141 11.00000 -1.20000 H13B 2 0.689187 0.817525 0.702290 11.00000 -1.20000 AFIX 0 C14 1 0.851681 0.973448 0.758726 11.00000 0.08285 0.05615 = 0.07047 0.01370 0.01222 -0.00491 AFIX 23 H14A 2 0.962809 0.989088 0.779568 11.00000 -1.20000 H14B 2 0.832309 1.002323 0.694287 11.00000 -1.20000 AFIX 0 C15 1 0.766074 1.046700 0.866199 11.00000 0.09729 0.04809 = 0.05814 0.01255 0.01236 -0.00572 C16 1 0.609642 1.077713 0.865479 11.00000 0.09300 0.04633 = 0.05573 0.01593 0.01842 -0.00722 C17 1 0.495818 1.058461 0.773487 11.00000 0.08784 0.05832 = 0.06669 0.01979 0.01829 -0.00871 AFIX 43 H17 2 0.515350 1.015032 0.693211 11.00000 -1.20000 AFIX 0 C18 1 0.354246 1.105523 0.805025 11.00000 0.09020 0.07087 = 0.10211 0.03607 0.02036 -0.00794 C19 1 0.324639 1.169144 0.926913 11.00000 0.10820 0.08404 = 0.11452 0.04034 0.05061 0.00866 AFIX 43 H19 2 0.228019 1.198703 0.946485 11.00000 -1.20000 AFIX 0 C20 1 0.433104 1.188451 1.016431 11.00000 0.13497 0.06708 = 0.08350 0.02428 0.05472 0.00807 AFIX 43 H20 2 0.411922 1.230965 1.096515 11.00000 -1.20000 AFIX 0 C21 1 0.576306 1.143463 0.986052 11.00000 0.11758 0.05478 = 0.05876 0.01809 0.02562 -0.00134 C22 1 0.819700 1.093420 0.983688 11.00000 0.11804 0.06333 = 0.06540 0.01541 0.00208 0.00222 AFIX 43 H22 2 0.918591 1.086419 1.010681 11.00000 -1.20000 AFIX 0 C23 1 0.253508 1.034043 0.601619 11.00000 0.12602 0.07652 = 0.12742 0.01930 -0.03484 -0.00862 AFIX 137 H23A 2 0.160526 1.034252 0.556920 11.00000 -1.50000 H23B 2 0.271971 0.948731 0.586374 11.00000 -1.50000 H23C 2 0.340490 1.075381 0.577137 11.00000 -1.50000 AFIX 0 HKLF 4 REM zhzhw_1010_auto_a.res in P-1 REM wR2 = 0.1903, GooF = S = 1.057, Restrained GooF = 1.057 for all data REM R1 = 0.0624 for 3095 Fo > 4sig(Fo) and 0.0843 for all 4395 data REM 284 parameters refined using 0 restraints END WGHT 0.0802 0.2648 REM Highest difference peak 0.525, deepest hole -0.268, 1-sigma level 0.037 Q1 1 1.0445 0.6741 0.1267 11.00000 0.05 0.53 ; _shelx_res_checksum 79165 _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 1.713 _oxdiff_exptl_absorpt_empirical_full_min 0.792 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 1.0554(3) 0.7689(2) 0.42707(19) 0.0996(7) Uani 1 1 d . . . . . O2 O 1.0369(2) 0.6008(2) 0.25982(17) 0.0917(6) Uani 1 1 d . . . . . O3 O 0.7184(2) 0.26053(15) 0.32231(15) 0.0811(5) Uani 1 1 d . . . . . H3 H 0.651326 0.228324 0.352592 0.122 Uiso 1 1 calc GR . . . . O4 O 0.5439(2) 0.25143(15) 0.49701(16) 0.0764(5) Uani 1 1 d . . . . . O5 O 0.53797(18) 0.42621(14) 0.66151(14) 0.0668(4) Uani 1 1 d . . . . . O6 O 0.2352(3) 1.0983(2) 0.7256(3) 0.1105(7) Uani 1 1 d . . . . . N1 N 0.8726(2) 0.76794(18) 0.60412(18) 0.0726(6) Uani 1 1 d . . . . . H1 H 0.941949 0.810045 0.579515 0.087 Uiso 1 1 calc R . . . . N2 N 0.7069(4) 1.1519(2) 1.0558(2) 0.0921(8) Uani 1 1 d . . . . . H2 H 0.716348 1.188412 1.132907 0.111 Uiso 1 1 calc R . . . . C1 C 0.8361(2) 0.6426(2) 0.5355(2) 0.0578(5) Uani 1 1 d . . . . . C2 C 0.8985(2) 0.5848(2) 0.4213(2) 0.0582(5) Uani 1 1 d . . . . . C3 C 0.8573(3) 0.4577(2) 0.3545(2) 0.0628(5) Uani 1 1 d . . . . . H3A H 0.899929 0.420478 0.280246 0.075 Uiso 1 1 calc R . . . . C4 C 0.7546(3) 0.3848(2) 0.3951(2) 0.0603(5) Uani 1 1 d . . . . . C5 C 0.6924(2) 0.44006(19) 0.50693(19) 0.0551(5) Uani 1 1 d . . . . . C6 C 0.7339(2) 0.5673(2) 0.5757(2) 0.0577(5) Uani 1 1 d . . . . . H6 H 0.692320 0.603199 0.650568 0.069 Uiso 1 1 calc R . . . . C7 C 1.0037(3) 0.6612(2) 0.3722(2) 0.0677(6) Uani 1 1 d . . . . . C8 C 1.1324(5) 0.6763(4) 0.2062(3) 0.1132(12) Uani 1 1 d . . . . . H8A H 1.071759 0.738402 0.195697 0.136 Uiso 1 1 calc R . . . . H8B H 1.222211 0.720623 0.259931 0.136 Uiso 1 1 calc R . . . . C9 C 1.1817(7) 0.6008(5) 0.0966(4) 0.167(2) Uani 1 1 d . . . . . H9A H 1.097460 0.578279 0.036745 0.251 Uiso 1 1 calc GR . . . . H9B H 1.214676 0.525925 0.102117 0.251 Uiso 1 1 calc GR . . . . H9C H 1.267360 0.645656 0.074468 0.251 Uiso 1 1 calc GR . . . . C10 C 0.5855(3) 0.3629(2) 0.5528(2) 0.0590(5) Uani 1 1 d . . . . . C11 C 0.4340(3) 0.3562(2) 0.7141(2) 0.0719(6) Uani 1 1 d . . . . . H11A H 0.486109 0.290286 0.725521 0.086 Uiso 1 1 calc R . . . . H11B H 0.341487 0.317637 0.661529 0.086 Uiso 1 1 calc R . . . . C12 C 0.3904(4) 0.4480(3) 0.8329(3) 0.0924(9) Uani 1 1 d . . . . . H12A H 0.333830 0.509993 0.820046 0.139 Uiso 1 1 calc GR . . . . H12B H 0.483221 0.488752 0.882534 0.139 Uiso 1 1 calc GR . . . . H12C H 0.326285 0.403962 0.872119 0.139 Uiso 1 1 calc GR . . . . C13 C 0.8018(3) 0.8330(2) 0.7148(2) 0.0687(6) Uani 1 1 d . . . . . H13A H 0.832643 0.801541 0.775141 0.082 Uiso 1 1 calc R . . . . H13B H 0.689187 0.817525 0.702290 0.082 Uiso 1 1 calc R . . . . C14 C 0.8517(3) 0.9734(2) 0.7587(2) 0.0737(7) Uani 1 1 d . . . . . H14A H 0.962809 0.989088 0.779568 0.088 Uiso 1 1 calc R . . . . H14B H 0.832309 1.002323 0.694287 0.088 Uiso 1 1 calc R . . . . C15 C 0.7661(3) 1.0467(2) 0.8662(2) 0.0710(6) Uani 1 1 d . . . . . C16 C 0.6096(3) 1.0777(2) 0.8655(2) 0.0669(6) Uani 1 1 d . . . . . C17 C 0.4958(3) 1.0585(2) 0.7735(2) 0.0732(7) Uani 1 1 d . . . . . H17 H 0.515350 1.015032 0.693211 0.088 Uiso 1 1 calc R . . . . C18 C 0.3542(4) 1.1055(3) 0.8050(3) 0.0878(8) Uani 1 1 d . . . . . C19 C 0.3246(4) 1.1691(3) 0.9269(4) 0.1012(10) Uani 1 1 d . . . . . H19 H 0.228019 1.198703 0.946485 0.121 Uiso 1 1 calc R . . . . C20 C 0.4331(5) 1.1885(3) 1.0164(3) 0.0962(10) Uani 1 1 d . . . . . H20 H 0.411922 1.230965 1.096515 0.115 Uiso 1 1 calc R . . . . C21 C 0.5763(4) 1.1435(2) 0.9861(2) 0.0786(8) Uani 1 1 d . . . . . C22 C 0.8197(4) 1.0934(3) 0.9837(3) 0.0855(8) Uani 1 1 d . . . . . H22 H 0.918591 1.086419 1.010681 0.103 Uiso 1 1 calc R . . . . C23 C 0.2535(5) 1.0340(3) 0.6016(4) 0.1176(12) Uani 1 1 d . . . . . H23A H 0.160526 1.034252 0.556920 0.176 Uiso 1 1 calc GR . . . . H23B H 0.271971 0.948731 0.586374 0.176 Uiso 1 1 calc GR . . . . H23C H 0.340490 1.075381 0.577137 0.176 Uiso 1 1 calc GR . . . . 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 0.1158(15) 0.0881(14) 0.0796(13) 0.0235(11) 0.0215(11) -0.0288(11) O2 0.1070(14) 0.0957(14) 0.0657(12) 0.0262(10) 0.0295(10) -0.0053(11) O3 0.1129(14) 0.0576(9) 0.0571(10) 0.0071(8) 0.0114(9) -0.0045(9) O4 0.0871(11) 0.0552(9) 0.0752(11) 0.0150(8) 0.0092(9) -0.0072(8) O5 0.0791(10) 0.0605(9) 0.0591(10) 0.0232(8) 0.0097(8) -0.0037(7) O6 0.0853(14) 0.1144(18) 0.135(2) 0.0538(17) 0.0059(14) -0.0011(12) N1 0.0821(13) 0.0531(10) 0.0698(13) 0.0115(9) 0.0239(10) -0.0056(9) N2 0.147(2) 0.0662(13) 0.0521(13) 0.0113(10) 0.0135(14) 0.0039(14) C1 0.0594(11) 0.0536(11) 0.0569(13) 0.0178(10) 0.0034(9) 0.0036(9) C2 0.0572(11) 0.0628(12) 0.0549(12) 0.0222(10) 0.0071(9) 0.0080(9) C3 0.0717(13) 0.0655(13) 0.0493(12) 0.0186(10) 0.0095(10) 0.0114(10) C4 0.0711(13) 0.0534(11) 0.0506(12) 0.0140(10) 0.0004(10) 0.0045(10) C5 0.0591(11) 0.0525(11) 0.0511(12) 0.0174(9) 0.0006(9) 0.0039(9) C6 0.0628(12) 0.0548(11) 0.0515(12) 0.0156(9) 0.0091(9) 0.0053(9) C7 0.0666(13) 0.0761(16) 0.0627(15) 0.0295(13) 0.0083(11) 0.0056(11) C8 0.127(3) 0.120(3) 0.090(2) 0.043(2) 0.042(2) -0.015(2) C9 0.199(5) 0.154(4) 0.113(3) 0.025(3) 0.059(3) -0.051(4) C10 0.0634(12) 0.0542(12) 0.0567(13) 0.0191(10) 0.0009(10) 0.0022(9) C11 0.0725(14) 0.0747(15) 0.0738(16) 0.0366(13) 0.0081(12) -0.0028(11) C12 0.104(2) 0.105(2) 0.0725(18) 0.0398(17) 0.0216(16) 0.0058(17) C13 0.0799(14) 0.0559(12) 0.0609(14) 0.0132(11) 0.0134(11) -0.0014(10) C14 0.0829(15) 0.0561(13) 0.0705(16) 0.0137(11) 0.0122(12) -0.0049(11) C15 0.0973(18) 0.0481(11) 0.0581(14) 0.0126(10) 0.0124(12) -0.0057(11) C16 0.0930(17) 0.0463(11) 0.0557(13) 0.0159(10) 0.0184(12) -0.0072(10) C17 0.0878(17) 0.0583(13) 0.0667(15) 0.0198(11) 0.0183(13) -0.0087(12) C18 0.0902(19) 0.0709(16) 0.102(2) 0.0361(16) 0.0204(17) -0.0079(14) C19 0.108(2) 0.084(2) 0.115(3) 0.040(2) 0.051(2) 0.0087(17) C20 0.135(3) 0.0671(16) 0.083(2) 0.0243(15) 0.055(2) 0.0081(17) C21 0.118(2) 0.0548(13) 0.0588(15) 0.0181(11) 0.0256(15) -0.0013(13) C22 0.118(2) 0.0633(15) 0.0654(17) 0.0154(13) 0.0021(15) 0.0022(14) C23 0.126(3) 0.0765(19) 0.127(3) 0.019(2) -0.035(2) -0.0086(18) 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_ _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 C7 O2 C8 115.2(2) . . ? C10 O5 C11 117.06(18) . . ? C18 O6 C23 118.4(3) . . ? C1 N1 C13 123.68(18) . . ? C22 N2 C21 109.3(2) . . ? N1 C1 C2 121.68(19) . . ? N1 C1 C6 120.7(2) . . ? C6 C1 C2 117.7(2) . . ? C1 C2 C7 120.0(2) . . ? C3 C2 C1 119.7(2) . . ? C3 C2 C7 120.3(2) . . ? C4 C3 C2 121.9(2) . . ? O3 C4 C3 118.0(2) . . ? O3 C4 C5 122.9(2) . . ? C3 C4 C5 119.1(2) . . ? C4 C5 C6 119.71(19) . . ? C4 C5 C10 119.77(19) . . ? C6 C5 C10 120.51(19) . . ? C5 C6 C1 121.9(2) . . ? O1 C7 O2 121.2(2) . . ? O1 C7 C2 124.8(2) . . ? O2 C7 C2 113.9(2) . . ? C9 C8 O2 110.7(3) . . ? O4 C10 O5 122.6(2) . . ? O4 C10 C5 123.8(2) . . ? O5 C10 C5 113.64(18) . . ? O5 C11 C12 107.3(2) . . ? N1 C13 C14 110.13(19) . . ? C15 C14 C13 111.92(19) . . ? C16 C15 C14 126.4(2) . . ? C22 C15 C14 127.0(3) . . ? C22 C15 C16 106.5(2) . . ? C17 C16 C15 133.7(2) . . ? C21 C16 C15 107.0(2) . . ? C21 C16 C17 119.3(3) . . ? C18 C17 C16 118.6(3) . . ? O6 C18 C17 125.1(3) . . ? O6 C18 C19 114.5(3) . . ? C17 C18 C19 120.3(3) . . ? C20 C19 C18 121.8(3) . . ? C19 C20 C21 118.5(3) . . ? N2 C21 C16 107.3(3) . . ? N2 C21 C20 131.2(3) . . ? C20 C21 C16 121.5(3) . . ? N2 C22 C15 109.9(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 C7 1.201(3) . ? O2 C7 1.315(3) . ? O2 C8 1.468(3) . ? O3 C4 1.370(3) . ? O4 C10 1.219(3) . ? O5 C10 1.326(3) . ? O5 C11 1.457(3) . ? O6 C18 1.367(4) . ? O6 C23 1.410(4) . ? N1 C1 1.369(3) . ? N1 C13 1.435(3) . ? N2 C21 1.368(4) . ? N2 C22 1.363(4) . ? C1 C2 1.419(3) . ? C1 C6 1.396(3) . ? C2 C3 1.387(3) . ? C2 C7 1.485(3) . ? C3 C4 1.383(3) . ? C4 C5 1.392(3) . ? C5 C6 1.393(3) . ? C5 C10 1.475(3) . ? C8 C9 1.375(5) . ? C11 C12 1.499(4) . ? C13 C14 1.518(3) . ? C14 C15 1.499(3) . ? C15 C16 1.429(4) . ? C15 C22 1.363(4) . ? C16 C17 1.407(4) . ? C16 C21 1.407(3) . ? C17 C18 1.383(4) . ? C18 C19 1.408(5) . ? C19 C20 1.354(5) . ? C20 C21 1.385(5) . ?