#------------------------------------------------------------------------------ #$Date: 2020-03-05 01:49:55 +0200 (Thu, 05 Mar 2020) $ #$Revision: 248873 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/70/1557045.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_1557045 loop_ _publ_author_name 'Burg, Finn' 'Breitenlechner, Stefan' 'Jandl, Christian' 'Bach, Thorsten' _publ_section_title ; Enantioselective oxygenation of exocyclic methylene groups by a manganese porphyrin catalyst with a chiral recognition site ; _journal_issue 8 _journal_name_full 'Chemical Science' _journal_page_first 2121 _journal_paper_doi 10.1039/C9SC06089H _journal_volume 11 _journal_year 2020 _chemical_absolute_configuration ad _chemical_compound_source 'see text' _chemical_formula_moiety 'C17 H14 Cl N O2' _chemical_formula_sum 'C17 H14 Cl N O2' _chemical_formula_weight 299.74 _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_update_record ; 2019-11-25 deposited with the CCDC. 2020-01-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.3182(4) _cell_length_b 10.9400(7) _cell_length_c 23.9705(16) _cell_measurement_reflns_used 9204 _cell_measurement_temperature 123 _cell_measurement_theta_max 26.9031 _cell_measurement_theta_min 2.5491 _cell_volume 1394.63(17) _computing_cell_refinement 'SAINT (Bruker, 2017)' _computing_data_collection 'APEX III Control Software (Bruker, 2016)' _computing_data_reduction 'SAINT (Bruker, 2017)' _computing_molecular_graphics 'PLATON (Spek, 2011)' _computing_publication_material 'PLATON (Spek, 2011), enCIFer (Allen, 2014)' _computing_structure_refinement 'SHELXL (Sheldrick, 2017), SHELXLE (Huebschle, 2011)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 123 _diffrn_detector ' CMOS plate ' _diffrn_detector_area_resol_mean 16 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker Photon CMOS ' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_radiation_monochromator 'Helios optic' _diffrn_radiation_probe x-ray _diffrn_radiation_source 'TXS rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_unetI/netI 0.0107 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 37764 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 25.24 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.52 _exptl_absorpt_coefficient_mu 0.277 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.7196 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 2016/2, Bruker, 2016' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description fragment _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.444 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.186 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.042 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.022(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 195 _refine_ls_number_reflns 2851 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.078 _refine_ls_R_factor_all 0.0270 _refine_ls_R_factor_gt 0.0268 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'W=1/[\S^2^(FO^2^)+(0.0421P)^2^+0.4183P] WHERE P=(FO^2^+2FC^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0737 _refine_ls_wR_factor_ref 0.0741 _reflns_number_gt 2821 _reflns_number_total 2851 _reflns_threshold_expression I>2\s(I) _cod_data_source_file c9sc06089h2.cif _cod_data_source_block compound_5 _cod_depositor_comments 'Adding full bibliography for 1557045.cif.' _cod_database_code 1557045 _shelx_res_file ; TITL BurFi1_0m_a.res in P2(1)2(1)2(1) BurFi1_0m.res created by SHELXL-2017/1 at 12:37:46 on 05-Nov-2019 CELL 0.71073 5.3182 10.9400 23.9705 90.000 90.000 90.000 ZERR 4.00 0.0004 0.0007 0.0016 0.000 0.000 0.000 LATT -1 SYMM x+1/2, -y+1/2, -z SYMM -x, y+1/2, -z+1/2 SYMM -x+1/2, -y, z+1/2 SFAC C H N O CL UNIT 68 56 4 8 4 LIST 4 TEMP -150 SIZE 0.110 0.250 0.444 ACTA OMIT 0 1 1 ! affected by beamstop L.S. 5 FMAP -2 PLAN -20 HTAB BOND $H CONF WGHT 0.042100 0.418300 FVAR 0.94314 CL1 5 0.462106 0.458362 0.510354 11.00000 0.05570 0.03254 = 0.02125 0.00768 -0.00311 0.00816 O1 4 0.913715 0.383328 0.769940 11.00000 0.02666 0.02335 = 0.02534 -0.00206 0.00050 -0.00790 O2 4 0.719155 0.046190 0.700100 11.00000 0.02591 0.01568 = 0.02514 -0.00157 -0.00331 0.00260 N1 3 0.646456 0.352320 0.843713 11.00000 0.02184 0.01885 = 0.01894 -0.00216 -0.00373 -0.00116 C1 1 0.748570 0.320637 0.793043 11.00000 0.02011 0.01913 = 0.02014 0.00078 -0.00453 0.00017 C2 1 0.656801 0.208264 0.767241 11.00000 0.02091 0.01607 = 0.01822 0.00112 -0.00425 0.00099 C3 1 0.467518 0.144175 0.790964 11.00000 0.02335 0.01604 = 0.02117 -0.00015 -0.00355 -0.00045 AFIX 43 H3 2 0.407648 0.072259 0.773160 11.00000 -1.20000 AFIX 0 C4 1 0.355940 0.182393 0.842189 11.00000 0.02362 0.01811 = 0.02095 0.00302 -0.00169 0.00130 C5 1 0.156984 0.117865 0.866985 11.00000 0.03018 0.02176 = 0.03031 0.00203 0.00260 -0.00276 AFIX 43 H5 2 0.091597 0.047318 0.848996 11.00000 -1.20000 AFIX 0 C6 1 0.055243 0.155201 0.916925 11.00000 0.03405 0.02776 = 0.03062 0.00573 0.00860 -0.00133 AFIX 43 H6 2 -0.080270 0.111289 0.933208 11.00000 -1.20000 AFIX 0 C7 1 0.153140 0.258062 0.943324 11.00000 0.03600 0.02964 = 0.02273 0.00282 0.00711 0.00675 AFIX 43 H7 2 0.084522 0.283204 0.978069 11.00000 -1.20000 AFIX 0 C8 1 0.347813 0.324373 0.920121 11.00000 0.03284 0.02196 = 0.02029 -0.00002 -0.00096 0.00490 AFIX 43 H8 2 0.411258 0.394524 0.938763 11.00000 -1.20000 AFIX 0 C9 1 0.451654 0.287892 0.868958 11.00000 0.02226 0.01868 = 0.01879 0.00260 -0.00382 0.00357 C10 1 0.742297 0.462461 0.871456 11.00000 0.02896 0.02860 = 0.02750 -0.01111 -0.00064 -0.00823 AFIX 137 H10A 2 0.885032 0.495056 0.850306 11.00000 -1.50000 H10B 2 0.797020 0.441770 0.909336 11.00000 -1.50000 H10C 2 0.608836 0.524104 0.873252 11.00000 -1.50000 AFIX 0 C11 1 0.778214 0.169813 0.713162 11.00000 0.01907 0.01691 = 0.02028 -0.00086 -0.00270 -0.00022 AFIX 13 H11 2 0.964721 0.177334 0.717207 11.00000 -1.20000 AFIX 0 C12 1 0.694915 0.246904 0.663515 11.00000 0.02205 0.01581 = 0.01954 -0.00197 -0.00099 -0.00141 C13 1 0.833277 0.240695 0.614632 11.00000 0.03670 0.02859 = 0.02678 0.00313 0.00798 0.01306 AFIX 43 H13 2 0.980115 0.191308 0.613489 11.00000 -1.20000 AFIX 0 C14 1 0.762088 0.305068 0.567262 11.00000 0.04856 0.03048 = 0.01981 0.00231 0.01054 0.01157 AFIX 43 H14 2 0.858603 0.300187 0.533987 11.00000 -1.20000 AFIX 0 C15 1 0.550143 0.375615 0.569537 11.00000 0.03869 0.01958 = 0.01833 0.00284 -0.00439 -0.00019 C16 1 0.408355 0.384391 0.617108 11.00000 0.03001 0.03199 = 0.02815 0.00599 0.00031 0.00941 AFIX 43 H16 2 0.261981 0.434142 0.617821 11.00000 -1.20000 AFIX 0 C17 1 0.481665 0.319275 0.664563 11.00000 0.02635 0.02847 = 0.02036 0.00412 0.00279 0.00481 AFIX 43 H17 2 0.384500 0.324745 0.697725 11.00000 -1.20000 AFIX 0 H2 2 0.835395 -0.000369 0.715850 11.00000 0.04736 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM BurFi1_0m_a.res in P2(1)2(1)2(1) REM R1 = 0.0268 for 2821 Fo > 4sig(Fo) and 0.0270 for all 2851 data REM 195 parameters refined using 0 restraints END WGHT 0.0421 0.4182 REM Instructions for potential hydrogen bonds EQIV $1 -x+2, y+1/2, -z+3/2 HTAB C10 O2_$1 EQIV $2 -x+3/2, -y+1, z+1/2 HTAB C10 Cl1_$2 EQIV $3 -x+1, y+1/2, -z+3/2 HTAB C10 O2_$3 EQIV $4 -x+2, y-1/2, -z+3/2 HTAB O2 O1_$4 REM Highest difference peak 0.186, deepest hole -0.348, 1-sigma level 0.042 Q1 1 0.5602 0.4837 0.5133 11.00000 0.05 -0.35 Q2 1 0.4629 0.4241 0.5065 11.00000 0.05 -0.26 Q3 1 0.4030 0.4669 0.5183 11.00000 0.05 -0.25 Q4 1 0.5287 0.2676 0.8371 11.00000 0.05 -0.19 Q5 1 0.8237 0.1424 0.6892 11.00000 0.05 -0.19 Q6 1 0.9705 0.4746 0.7292 11.00000 0.05 0.19 Q7 1 0.3063 0.4186 0.5076 11.00000 0.05 0.18 Q8 1 0.7143 0.1860 0.7412 11.00000 0.05 0.18 Q9 1 0.6552 0.1372 0.7023 11.00000 0.05 -0.18 Q10 1 0.7825 0.3945 0.4951 11.00000 0.05 0.17 Q11 1 0.7584 0.3741 0.8049 11.00000 0.05 -0.16 Q12 1 0.2476 0.1592 0.8536 11.00000 0.05 0.16 Q13 1 0.4629 0.4409 0.5658 11.00000 0.05 -0.16 Q14 1 0.6282 0.1541 0.7889 11.00000 0.05 0.15 Q15 1 0.2952 0.1398 0.8636 11.00000 0.05 0.15 Q16 1 0.8107 0.1210 0.7329 11.00000 0.05 -0.15 Q17 1 0.3982 0.3043 0.8978 11.00000 0.05 0.14 Q18 1 1.0972 0.3624 0.7952 11.00000 0.05 0.14 Q19 1 0.3886 0.2833 0.7704 11.00000 0.05 0.13 Q20 1 0.4068 0.2277 0.8555 11.00000 0.05 0.13 ; _shelx_res_checksum 25134 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z 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 Cl1 0.0557(3) 0.0325(3) 0.0212(2) 0.0077(2) -0.0031(2) 0.0082(3) O1 0.0267(7) 0.0233(7) 0.0253(7) -0.0021(5) 0.0005(6) -0.0079(6) O2 0.0259(7) 0.0157(6) 0.0251(7) -0.0016(5) -0.0033(6) 0.0026(6) N1 0.0218(7) 0.0188(7) 0.0189(7) -0.0022(6) -0.0037(6) -0.0012(6) C1 0.0201(8) 0.0191(8) 0.0201(8) 0.0008(7) -0.0045(7) 0.0002(7) C2 0.0209(8) 0.0161(8) 0.0182(8) 0.0011(7) -0.0043(7) 0.0010(7) C3 0.0233(9) 0.0160(8) 0.0212(8) -0.0002(7) -0.0036(8) -0.0005(7) C4 0.0236(9) 0.0181(8) 0.0209(9) 0.0030(7) -0.0017(7) 0.0013(8) C5 0.0302(10) 0.0218(9) 0.0303(10) 0.0020(8) 0.0026(9) -0.0028(8) C6 0.0341(11) 0.0278(10) 0.0306(10) 0.0057(8) 0.0086(9) -0.0013(9) C7 0.0360(11) 0.0296(10) 0.0227(9) 0.0028(8) 0.0071(8) 0.0067(9) C8 0.0328(10) 0.0220(9) 0.0203(9) 0.0000(8) -0.0010(8) 0.0049(9) C9 0.0223(8) 0.0187(8) 0.0188(8) 0.0026(7) -0.0038(7) 0.0036(7) C10 0.0290(10) 0.0286(10) 0.0275(10) -0.0111(8) -0.0006(8) -0.0082(9) C11 0.0191(8) 0.0169(8) 0.0203(8) -0.0009(7) -0.0027(7) -0.0002(7) C12 0.0220(9) 0.0158(8) 0.0195(8) -0.0020(7) -0.0010(7) -0.0014(7) C13 0.0367(11) 0.0286(10) 0.0268(10) 0.0031(9) 0.0080(9) 0.0131(10) C14 0.0486(13) 0.0305(11) 0.0198(9) 0.0023(8) 0.0105(10) 0.0116(10) C15 0.0387(11) 0.0196(8) 0.0183(8) 0.0028(7) -0.0044(8) -0.0002(8) C16 0.0300(10) 0.0320(10) 0.0281(10) 0.0060(9) 0.0003(9) 0.0094(9) C17 0.0264(9) 0.0285(10) 0.0204(9) 0.0041(8) 0.0028(8) 0.0048(9) loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cl1 Cl Uani 0.46211(12) 0.45836(5) 0.51035(2) 1.000 0.0365(2) d . O1 O Uani 0.9137(3) 0.38333(13) 0.76994(6) 1.000 0.0251(4) d . O2 O Uani 0.7192(3) 0.04619(12) 0.70010(6) 1.000 0.0222(4) d . N1 N Uani 0.6465(3) 0.35232(14) 0.84371(7) 1.000 0.0198(4) d . C1 C Uani 0.7486(3) 0.32064(17) 0.79304(8) 1.000 0.0198(5) d . C2 C Uani 0.6568(4) 0.20826(16) 0.76724(8) 1.000 0.0184(5) d . C3 C Uani 0.4675(4) 0.14418(16) 0.79096(8) 1.000 0.0202(5) d . C4 C Uani 0.3559(4) 0.18239(17) 0.84219(8) 1.000 0.0209(5) d . C5 C Uani 0.1570(4) 0.11786(19) 0.86698(9) 1.000 0.0274(6) d . C6 C Uani 0.0552(4) 0.1552(2) 0.91692(9) 1.000 0.0308(6) d . C7 C Uani 0.1531(4) 0.2581(2) 0.94332(8) 1.000 0.0294(6) d . C8 C Uani 0.3478(4) 0.32437(18) 0.92012(8) 1.000 0.0250(5) d . C9 C Uani 0.4517(4) 0.28789(16) 0.86896(7) 1.000 0.0199(5) d . C10 C Uani 0.7423(4) 0.4625(2) 0.87146(9) 1.000 0.0284(6) d . C11 C Uani 0.7782(3) 0.16981(16) 0.71316(8) 1.000 0.0188(5) d . C12 C Uani 0.6949(3) 0.24690(16) 0.66352(8) 1.000 0.0191(5) d . C13 C Uani 0.8333(4) 0.2407(2) 0.61463(9) 1.000 0.0307(6) d . C14 C Uani 0.7621(5) 0.3051(2) 0.56726(9) 1.000 0.0330(6) d . C15 C Uani 0.5501(4) 0.37561(18) 0.56954(8) 1.000 0.0255(5) d . C16 C Uani 0.4084(4) 0.3844(2) 0.61711(9) 1.000 0.0300(6) d . C17 C Uani 0.4817(4) 0.31927(19) 0.66456(8) 1.000 0.0251(5) d . H2 H Uiso 0.835(6) 0.000(3) 0.7159(13) 1.000 0.047(8) d . H3 H Uiso 0.40765 0.07226 0.77316 1.000 0.0240 c RU H5 H Uiso 0.09160 0.04732 0.84900 1.000 0.0330 c RU H6 H Uiso -0.08027 0.11129 0.93321 1.000 0.0370 c RU H7 H Uiso 0.08452 0.28320 0.97807 1.000 0.0350 c RU H8 H Uiso 0.41126 0.39452 0.93876 1.000 0.0300 c RU H10A H Uiso 0.88503 0.49506 0.85031 1.000 0.0430 c RU H10B H Uiso 0.79702 0.44177 0.90934 1.000 0.0430 c RU H10C H Uiso 0.60884 0.52410 0.87325 1.000 0.0430 c RU H11 H Uiso 0.96472 0.17733 0.71721 1.000 0.0230 c RU H13 H Uiso 0.98011 0.19131 0.61349 1.000 0.0370 c RU H14 H Uiso 0.85860 0.30019 0.53399 1.000 0.0400 c RU H16 H Uiso 0.26198 0.43414 0.61782 1.000 0.0360 c RU H17 H Uiso 0.38450 0.32474 0.69772 1.000 0.0300 c RU loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 ' 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' Cl Cl 0.1484 0.1585 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 ' 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_publ_flag C1 N1 C9 123.41(15) yes C1 N1 C10 118.05(16) yes C9 N1 C10 118.50(16) yes C11 O2 H2 107(2) no O1 C1 C2 120.77(17) yes N1 C1 C2 117.02(16) yes O1 C1 N1 122.21(17) yes C1 C2 C3 120.49(17) no C1 C2 C11 117.11(16) no C3 C2 C11 122.39(16) no C2 C3 C4 121.32(17) no C3 C4 C5 122.04(18) no C5 C4 C9 119.30(18) no C3 C4 C9 118.65(18) no C4 C5 C6 121.03(19) no C5 C6 C7 119.2(2) no C6 C7 C8 121.45(19) no C7 C8 C9 119.87(18) no N1 C9 C4 118.94(16) yes C4 C9 C8 119.11(18) no N1 C9 C8 121.96(17) yes O2 C11 C12 106.86(15) yes C2 C11 C12 113.10(14) no O2 C11 C2 111.09(15) yes C11 C12 C17 122.75(16) no C13 C12 C17 118.60(18) no C11 C12 C13 118.61(16) no C12 C13 C14 121.5(2) no C13 C14 C15 118.6(2) no Cl1 C15 C14 118.74(16) yes Cl1 C15 C16 119.49(16) yes C14 C15 C16 121.76(19) no C15 C16 C17 119.22(19) no C12 C17 C16 120.39(18) no C2 C3 H3 119.00 no C4 C3 H3 119.00 no C4 C5 H5 119.00 no C6 C5 H5 119.00 no C5 C6 H6 120.00 no C7 C6 H6 120.00 no C6 C7 H7 119.00 no C8 C7 H7 119.00 no C7 C8 H8 120.00 no C9 C8 H8 120.00 no N1 C10 H10A 109.00 no N1 C10 H10B 109.00 no N1 C10 H10C 109.00 no H10A C10 H10B 109.00 no H10A C10 H10C 110.00 no H10B C10 H10C 109.00 no O2 C11 H11 109.00 no C2 C11 H11 109.00 no C12 C11 H11 109.00 no C12 C13 H13 119.00 no C14 C13 H13 119.00 no C13 C14 H14 121.00 no C15 C14 H14 121.00 no C15 C16 H16 120.00 no C17 C16 H16 120.00 no C12 C17 H17 120.00 no C16 C17 H17 120.00 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C15 1.747(2) yes O1 C1 1.244(2) yes O2 C11 1.423(2) yes N1 C1 1.375(2) yes N1 C9 1.392(3) yes N1 C10 1.468(3) yes O2 H2 0.88(3) no C1 C2 1.460(3) no C2 C3 1.352(3) no C2 C11 1.508(3) no C3 C4 1.427(3) no C4 C9 1.415(3) no C4 C5 1.404(3) no C5 C6 1.376(3) no C6 C7 1.392(3) no C7 C8 1.381(3) no C8 C9 1.403(3) no C11 C12 1.524(3) no C12 C17 1.383(3) no C12 C13 1.386(3) no C13 C14 1.389(3) no C14 C15 1.367(3) no C15 C16 1.370(3) no C16 C17 1.398(3) no C3 H3 0.9500 no C5 H5 0.9500 no C6 H6 0.9500 no C7 H7 0.9500 no C8 H8 0.9500 no C10 H10A 0.9800 no C10 H10B 0.9800 no C10 H10C 0.9800 no C11 H11 1.0000 no C13 H13 0.9500 no C14 H14 0.9500 no C16 H16 0.9500 no C17 H17 0.9500 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O2 H2 O1 0.88(3) 1.88(3) 2.739(2) 164(3) 4_746 yes C3 H3 O2 0.9500 2.4300 2.772(2) 101.00 . yes C10 H10A O1 0.9800 2.2900 2.739(3) 107.00 . yes C10 H10A O2 0.9800 2.4900 3.462(3) 171.00 4_756 yes C10 H10C O2 0.9800 2.4900 3.131(3) 123.00 4_656 yes 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_publ_flag C9 N1 C1 O1 176.17(18) no C9 N1 C1 C2 -4.5(3) no C10 N1 C1 O1 -1.5(3) no C10 N1 C1 C2 177.81(17) no C1 N1 C9 C4 1.6(3) no C1 N1 C9 C8 -178.48(18) no C10 N1 C9 C4 179.22(17) no C10 N1 C9 C8 -0.8(3) no O1 C1 C2 C3 -176.26(18) no O1 C1 C2 C11 2.5(3) no N1 C1 C2 C3 4.4(3) no N1 C1 C2 C11 -176.86(16) no C1 C2 C3 C4 -1.4(3) no C11 C2 C3 C4 179.93(18) no C1 C2 C11 O2 165.21(16) no C1 C2 C11 C12 -74.6(2) no C3 C2 C11 O2 -16.1(3) no C3 C2 C11 C12 104.1(2) no C2 C3 C4 C5 179.1(2) no C2 C3 C4 C9 -1.7(3) no C3 C4 C5 C6 178.8(2) no C9 C4 C5 C6 -0.4(3) no C3 C4 C9 N1 1.7(3) no C3 C4 C9 C8 -178.30(18) no C5 C4 C9 N1 -179.10(18) no C5 C4 C9 C8 1.0(3) no C4 C5 C6 C7 -0.5(3) no C5 C6 C7 C8 0.9(3) no C6 C7 C8 C9 -0.3(3) no C7 C8 C9 N1 179.42(19) no C7 C8 C9 C4 -0.6(3) no O2 C11 C12 C13 -72.4(2) no O2 C11 C12 C17 105.2(2) no C2 C11 C12 C13 165.08(17) no C2 C11 C12 C17 -17.4(2) no C11 C12 C13 C14 177.58(19) no C17 C12 C13 C14 -0.1(3) no C11 C12 C17 C16 -177.45(18) no C13 C12 C17 C16 0.1(3) no C12 C13 C14 C15 -0.1(3) no C13 C14 C15 Cl1 179.17(17) no C13 C14 C15 C16 0.3(3) no Cl1 C15 C16 C17 -179.14(16) no C14 C15 C16 C17 -0.2(3) no C15 C16 C17 C12 0.1(3) no