#------------------------------------------------------------------------------ #$Date: 2026-06-04 10:23:32 +0100 (Thu, 04 Jun 2026) $ #$Revision: 306202 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577359.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_1577359 loop_ _publ_author_name 'Zhang, Qilong' 'Zhou, Xu' 'Shan, Xiaofeng' 'He, Fa' 'Bao, Yuwei' 'Xu, Hong' 'Zhu, Chun' 'Zhu, Bixue' _publ_section_title ; Switching between photochromism and photoluminescence in Schiff base derivatives by molecular design of end groups. ; _journal_issue 18 _journal_name_full 'Chemical science' _journal_page_first 9193 _journal_page_last 9203 _journal_paper_doi 10.1039/d6sc00735j _journal_volume 17 _journal_year 2026 _chemical_formula_moiety 'C37 H30 N O' _chemical_formula_sum 'C37 H33 N O' _chemical_formula_weight 507.64 _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 _audit_creation_date 2024-11-03 _audit_creation_method ; Olex2 1.2-beta (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2025-09-10 deposited with the CCDC. 2026-03-16 downloaded from the CCDC. ; _cell_angle_alpha 87.987(5) _cell_angle_beta 88.805(5) _cell_angle_gamma 86.401(5) _cell_formula_units_Z 2 _cell_length_a 6.1709(9) _cell_length_b 9.2484(12) _cell_length_c 25.973(4) _cell_measurement_reflns_used 5210 _cell_measurement_temperature 273.15 _cell_measurement_theta_max 28.28 _cell_measurement_theta_min 2.67 _cell_volume 1478.2(4) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _diffrn_ambient_temperature 273.15 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_unetI/netI 0.0429 _diffrn_reflns_Laue_measured_fraction_full 0.985 _diffrn_reflns_Laue_measured_fraction_max 0.985 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 12353 _diffrn_reflns_point_group_measured_fraction_full 0.985 _diffrn_reflns_point_group_measured_fraction_max 0.985 _diffrn_reflns_theta_full 24.994 _diffrn_reflns_theta_max 24.994 _diffrn_reflns_theta_min 3.140 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6318 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.141 _exptl_crystal_density_meas ? _exptl_crystal_description block _exptl_crystal_F_000 540 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.736 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 369 _refine_ls_number_reflns 5125 _refine_ls_number_restraints 49 _refine_ls_restrained_S_all 1.084 _refine_ls_R_factor_all 0.1352 _refine_ls_R_factor_gt 0.1055 _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^)+(0.1657P)^2^+1.2807P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2903 _refine_ls_wR_factor_ref 0.3100 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3624 _reflns_number_total 5125 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc00735j2.cif _cod_data_source_block aaa _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_crystal_density_meas' value 'none' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_database_code 1577359 _shelx_shelxl_version_number 2014/7 _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 0.988 _shelx_estimated_absorpt_t_min 0.986 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2. Rigid bond restraints C34, C35 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002 3. Uiso/Uaniso restraints and constraints Uanis(C29) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C37) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(C34) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C35) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(C29) = Uanis(C29A) Uanis(C30) = Uanis(C30A) Uanis(C32) = Uanis(C32A) Uanis(C33) = Uanis(C33A) 4. Others Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30A)=Sof(C32A)=Sof(H32A)=Sof(C33A)= Sof(H33A)=1-FVAR(1) Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33)=FVAR(1) 5.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C27(H27), C29(H29), C29A(H29A), C30(H30), C30A(H30A), C32(H32), C32A(H32A), C33(H33), C33A(H33A) 5.b Idealised Me refined as rotating group: C34(H34A,H34B,H34C), C36(H36A,H36C,H36B), C37(H37C,H37A,H37B) 5.c Idealised tetrahedral OH refined as rotating group: O1(H1) ; _shelx_res_file ; aaa.res created by SHELXL-2014/7 TITL AAA_a.res in P-1 CELL 0.71073 6.1709 9.2484 25.9732 87.987 88.805 86.401 ZERR 2 0.0009 0.0012 0.0037 0.005 0.005 0.005 LATT 1 SFAC C H N O UNIT 74 66 2 2 DELU 0.001 0.002 C34 C35 ISOR 0.01 0.02 C29 C30 C32 C33 C36 C37 ISOR 0.01 0.02 C34 C36 C37 C35 EADP C29 C29A EADP C30 C30A EADP C32 C32A EADP C33 C33A L.S. 20 PLAN 30 0 0 SIZE 0.18 0.2 0.21 TEMP 0 HTAB O1 N1 CONF MORE -1 fmap 2 acta OMIT 0 50 OMIT -2 1 1 REM REM REM WGHT 0.165700 1.280700 FVAR 1.72922 0.58567 O1 4 0.168781 0.707223 0.338879 11.00000 0.06726 0.10002 = 0.06420 -0.02173 0.00256 0.02346 AFIX 147 H1 2 0.229308 0.709559 0.366619 11.00000 -1.50000 AFIX 0 N1 3 0.497144 0.684667 0.401701 11.00000 0.07284 0.07923 = 0.04614 -0.01743 -0.00053 0.00562 C1 1 0.802763 0.265659 0.214194 11.00000 0.06633 0.04813 = 0.03810 -0.01055 -0.01018 0.00387 C2 1 0.670616 0.180106 0.244841 11.00000 0.09778 0.05173 = 0.04856 0.00114 0.00094 0.00361 AFIX 43 H2 2 0.528889 0.213635 0.252625 11.00000 -1.20000 AFIX 0 C3 1 0.748447 0.045227 0.263886 11.00000 0.15301 0.05236 = 0.05822 0.00103 -0.00840 0.00758 AFIX 43 H3 2 0.658505 -0.010626 0.284469 11.00000 -1.20000 AFIX 0 C4 1 0.951468 -0.005493 0.252991 11.00000 0.16509 0.05450 = 0.07214 -0.01313 -0.04347 0.03296 AFIX 43 H4 2 1.000810 -0.096814 0.265548 11.00000 -1.20000 AFIX 0 C5 1 1.087753 0.077058 0.223234 11.00000 0.09987 0.07625 = 0.09605 -0.03173 -0.03839 0.03551 AFIX 43 H5 2 1.229411 0.041899 0.216221 11.00000 -1.20000 AFIX 0 C6 1 1.013582 0.213610 0.203548 11.00000 0.07258 0.06645 = 0.06991 -0.02037 -0.01527 0.01312 AFIX 43 H6 2 1.105505 0.269162 0.183400 11.00000 -1.20000 AFIX 0 C7 1 0.711407 0.410397 0.193909 11.00000 0.04955 0.04566 = 0.04025 -0.00396 -0.00618 -0.00572 C8 1 0.741946 0.461764 0.145465 11.00000 0.05226 0.04749 = 0.04415 -0.00545 -0.00529 -0.01268 C9 1 0.854629 0.373477 0.104327 11.00000 0.06119 0.05161 = 0.03937 -0.00744 -0.00204 -0.01098 C10 1 0.790374 0.239039 0.092555 11.00000 0.09291 0.05868 = 0.05049 -0.01134 0.00257 -0.02032 AFIX 43 H10 2 0.673321 0.201192 0.110375 11.00000 -1.20000 AFIX 0 C11 1 0.895722 0.160279 0.055122 11.00000 0.11738 0.06733 = 0.06722 -0.02833 0.00272 -0.01759 AFIX 43 H11 2 0.849522 0.069581 0.047769 11.00000 -1.20000 AFIX 0 C12 1 1.068571 0.213152 0.028265 11.00000 0.10174 0.09680 = 0.06398 -0.03734 0.00727 0.00375 AFIX 43 H12 2 1.141889 0.158228 0.003309 11.00000 -1.20000 AFIX 0 C13 1 1.131799 0.348123 0.038716 11.00000 0.08836 0.10775 = 0.07838 -0.03260 0.03122 -0.02131 AFIX 43 H13 2 1.247995 0.385695 0.020474 11.00000 -1.20000 AFIX 0 C14 1 1.024677 0.428492 0.075995 11.00000 0.08187 0.07336 = 0.06671 -0.02014 0.01647 -0.02699 AFIX 43 H14 2 1.067092 0.520917 0.082223 11.00000 -1.20000 AFIX 0 C15 1 0.659502 0.610364 0.128416 11.00000 0.05321 0.05025 = 0.03913 0.00116 0.00114 -0.01144 C16 1 0.709144 0.733317 0.153129 11.00000 0.09730 0.05170 = 0.05877 0.00276 -0.02391 -0.01606 AFIX 43 H16 2 0.802254 0.724229 0.180912 11.00000 -1.20000 AFIX 0 C17 1 0.625759 0.867821 0.138037 11.00000 0.13328 0.05221 = 0.08045 0.00713 -0.02518 -0.01771 AFIX 43 H17 2 0.662939 0.948457 0.155531 11.00000 -1.20000 AFIX 0 C18 1 0.489698 0.885024 0.097925 11.00000 0.10480 0.06547 = 0.09161 0.02118 -0.00767 -0.00087 AFIX 43 H18 2 0.431122 0.976855 0.088287 11.00000 -1.20000 AFIX 0 C19 1 0.438197 0.766240 0.071418 11.00000 0.08002 0.09898 = 0.07299 0.02143 -0.02418 -0.00656 AFIX 43 H19 2 0.344838 0.777177 0.043710 11.00000 -1.20000 AFIX 0 C20 1 0.526692 0.629529 0.086322 11.00000 0.06813 0.06281 = 0.05631 -0.00017 -0.01175 -0.01191 AFIX 43 H20 2 0.495828 0.549677 0.067599 11.00000 -1.20000 AFIX 0 C21 1 0.570883 0.493083 0.231943 11.00000 0.05250 0.03995 = 0.04047 -0.00002 -0.00439 -0.00286 C22 1 0.355847 0.539867 0.220873 11.00000 0.05674 0.04882 = 0.04803 0.00086 -0.00715 -0.00174 C23 1 0.222970 0.611613 0.256816 11.00000 0.05110 0.06021 = 0.05786 -0.00159 -0.00413 0.00269 C24 1 0.302658 0.639702 0.304833 11.00000 0.05595 0.05369 = 0.04922 -0.00402 0.00157 0.00645 C25 1 0.519746 0.596040 0.316567 11.00000 0.05376 0.04822 = 0.04257 -0.00065 -0.00065 0.00058 C26 1 0.649020 0.521417 0.280236 11.00000 0.05239 0.05097 = 0.04077 -0.00460 -0.00207 -0.00046 C27 1 0.609312 0.625020 0.366146 11.00000 0.05755 0.06323 = 0.05247 -0.00828 -0.00345 0.00528 AFIX 43 H27 2 0.754891 0.598666 0.371968 11.00000 -1.20000 AFIX 0 C28 1 0.590008 0.713031 0.449333 11.00000 0.07247 0.07112 = 0.04090 -0.00864 -0.00537 0.00826 PART 1 C29 1 0.802123 0.741643 0.453867 21.00000 0.11333 0.13619 = 0.06278 -0.03690 0.01428 -0.02714 AFIX 43 H29 2 0.892870 0.740710 0.424824 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C29A 1 0.720591 0.629445 0.475693 -21.00000 0.11333 0.13619 = 0.06278 -0.03690 0.01428 -0.02714 AFIX 43 H29A 2 0.762802 0.540387 0.461879 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C30 1 0.884748 0.772154 0.501179 21.00000 0.10032 0.14077 = 0.06681 -0.02779 -0.00217 -0.02757 AFIX 43 H30 2 1.030848 0.790377 0.503005 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C30A 1 0.808029 0.658925 0.524105 -21.00000 0.10032 0.14077 = 0.06681 -0.02779 -0.00217 -0.02757 AFIX 43 H30A 2 0.904557 0.590630 0.539807 -21.00000 -1.20000 AFIX 0 PART 0 C31 1 0.757065 0.776663 0.546388 11.00000 0.07911 0.06886 = 0.04207 -0.00545 -0.00078 -0.00502 PART 1 C32 1 0.559983 0.727863 0.541248 21.00000 0.08421 0.10819 = 0.05261 -0.01719 0.00354 -0.00727 AFIX 43 H32 2 0.476275 0.712858 0.570920 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C32A 1 0.598058 0.875818 0.521431 -21.00000 0.08421 0.10819 = 0.05261 -0.01719 0.00354 -0.00727 AFIX 43 H32A 2 0.547474 0.959649 0.537730 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C33 1 0.471017 0.697671 0.493475 21.00000 0.07368 0.11308 = 0.06147 -0.01723 0.00075 -0.00580 AFIX 43 H33 2 0.330504 0.667175 0.492246 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C33A 1 0.521799 0.847066 0.474089 -21.00000 0.07368 0.11308 = 0.06147 -0.01723 0.00075 -0.00580 AFIX 43 H33A 2 0.425442 0.913900 0.457601 -21.00000 -1.20000 AFIX 0 PART 0 C34 1 0.989547 0.940032 0.591665 11.00000 0.18203 0.16832 = 0.10391 -0.01436 -0.03527 -0.07836 AFIX 137 H34A 2 1.097405 0.920484 0.565231 11.00000 -1.50000 H34B 2 1.059717 0.954248 0.623578 11.00000 -1.50000 H34C 2 0.901989 1.025888 0.582135 11.00000 -1.50000 AFIX 0 C35 1 0.846178 0.812420 0.598084 11.00000 0.09243 0.10299 = 0.04500 -0.00276 -0.00808 0.00130 C36 1 0.976112 0.691687 0.620791 11.00000 0.36453 0.19125 = 0.13914 -0.00740 -0.14677 0.04222 AFIX 137 H36A 2 0.886218 0.612152 0.628068 11.00000 -1.50000 H36C 2 1.037418 0.720712 0.652198 11.00000 -1.50000 H36B 2 1.090804 0.662189 0.597156 11.00000 -1.50000 AFIX 0 C37 1 0.670205 0.864733 0.634251 11.00000 0.16135 0.37737 = 0.08577 -0.10102 -0.01739 -0.00105 AFIX 137 H37C 2 0.561836 0.794700 0.637322 11.00000 -1.50000 H37A 2 0.605273 0.955446 0.621271 11.00000 -1.50000 H37B 2 0.730101 0.877766 0.667466 11.00000 -1.50000 AFIX 0 HKLF 4 REM AAA_a.res in P-1 REM R1 = 0.1055 for 3624 Fo > 4sig(Fo) and 0.1352 for all 5125 data REM 369 parameters refined using 49 restraints END WGHT 0.1658 1.2827 REM Highest difference peak 0.736, deepest hole -0.368, 1-sigma level 0.055 Q1 1 0.7552 0.6896 0.6388 11.00000 0.05 0.74 Q2 1 1.0957 0.8031 0.5978 11.00000 0.05 0.66 Q3 1 0.7983 0.4887 0.2918 11.00000 0.05 0.51 Q4 1 0.7731 0.9619 0.6137 11.00000 0.05 0.50 Q5 1 0.2969 0.5189 0.1875 11.00000 0.05 0.46 Q6 1 0.0654 0.6417 0.2499 11.00000 0.05 0.45 Q7 1 0.8248 0.6663 0.4643 11.00000 0.05 0.44 Q8 1 0.9163 0.7017 0.5119 11.00000 0.05 0.40 Q9 1 0.8272 0.8407 0.4944 11.00000 0.05 0.34 Q10 1 0.6642 0.6457 0.5363 11.00000 0.05 0.34 Q11 1 0.7416 0.8089 0.4507 11.00000 0.05 0.32 Q12 1 0.5697 0.6143 0.4901 11.00000 0.05 0.27 Q13 1 0.5861 0.8753 0.4691 11.00000 0.05 0.24 Q14 1 0.6723 0.9106 0.5101 11.00000 0.05 0.23 Q15 1 0.4465 0.8032 0.4817 11.00000 0.05 0.21 Q16 1 0.6005 0.4605 0.2607 11.00000 0.05 0.18 Q17 1 0.6813 0.4110 0.1633 11.00000 0.05 0.17 Q18 1 0.6417 0.5374 0.2495 11.00000 0.05 0.17 Q19 1 0.3652 0.7040 0.4022 11.00000 0.05 0.17 Q20 1 0.2378 0.5857 0.2812 11.00000 0.05 0.16 Q21 1 0.4270 0.4869 0.2310 11.00000 0.05 0.16 Q22 1 0.4575 0.5280 0.2219 11.00000 0.05 0.16 Q23 1 0.2804 0.7792 0.3390 11.00000 0.05 0.15 Q24 1 0.4707 0.5619 0.0841 11.00000 0.05 0.15 Q25 1 0.8758 0.4202 0.0760 11.00000 0.05 0.14 Q26 1 0.4246 0.6638 0.3003 11.00000 0.05 0.14 Q27 1 0.2872 0.6581 0.2664 11.00000 0.05 0.14 Q28 1 0.3831 0.5806 0.3147 11.00000 0.05 0.14 Q29 1 0.6876 0.3304 0.2001 11.00000 0.05 0.13 Q30 1 0.9562 0.0700 0.0610 11.00000 0.05 0.13 ; _shelx_res_checksum 99658 _olex2_submission_special_instructions 'No special instructions were received' 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 0.1688(5) 0.7072(4) 0.33888(11) 0.0780(9) Uani 1 1 d . . . . . H1 H 0.2293 0.7096 0.3666 0.117 Uiso 1 1 calc GR . . . . N1 N 0.4971(6) 0.6847(4) 0.40170(12) 0.0662(9) Uani 1 1 d . . . . . C1 C 0.8028(6) 0.2657(4) 0.21419(13) 0.0508(9) Uani 1 1 d . . . . . C2 C 0.6706(8) 0.1801(4) 0.24484(15) 0.0665(11) Uani 1 1 d . . . . . H2 H 0.5289 0.2136 0.2526 0.080 Uiso 1 1 calc R . . . . C3 C 0.7484(11) 0.0452(5) 0.26389(18) 0.0884(16) Uani 1 1 d . . . . . H3 H 0.6585 -0.0106 0.2845 0.106 Uiso 1 1 calc R . . . . C4 C 0.9515(13) -0.0055(6) 0.2530(2) 0.098(2) Uani 1 1 d . . . . . H4 H 1.0008 -0.0968 0.2655 0.118 Uiso 1 1 calc R . . . . C5 C 1.0878(10) 0.0771(6) 0.2232(2) 0.0913(17) Uani 1 1 d . . . . . H5 H 1.2294 0.0419 0.2162 0.110 Uiso 1 1 calc R . . . . C6 C 1.0136(7) 0.2136(5) 0.20355(17) 0.0698(12) Uani 1 1 d . . . . . H6 H 1.1055 0.2692 0.1834 0.084 Uiso 1 1 calc R . . . . C7 C 0.7114(5) 0.4104(4) 0.19391(13) 0.0449(8) Uani 1 1 d . . . . . C8 C 0.7419(6) 0.4618(4) 0.14547(13) 0.0474(8) Uani 1 1 d . . . . . C9 C 0.8546(6) 0.3735(4) 0.10433(13) 0.0503(9) Uani 1 1 d . . . . . C10 C 0.7904(8) 0.2390(4) 0.09256(15) 0.0665(11) Uani 1 1 d . . . . . H10 H 0.6733 0.2012 0.1104 0.080 Uiso 1 1 calc R . . . . C11 C 0.8957(9) 0.1603(5) 0.05512(18) 0.0829(14) Uani 1 1 d . . . . . H11 H 0.8495 0.0696 0.0478 0.100 Uiso 1 1 calc R . . . . C12 C 1.0686(9) 0.2132(6) 0.02826(19) 0.0872(15) Uani 1 1 d . . . . . H12 H 1.1419 0.1582 0.0033 0.105 Uiso 1 1 calc R . . . . C13 C 1.1318(9) 0.3481(6) 0.0387(2) 0.0906(16) Uani 1 1 d . . . . . H13 H 1.2480 0.3857 0.0205 0.109 Uiso 1 1 calc R . . . . C14 C 1.0247(8) 0.4285(5) 0.07599(17) 0.0729(12) Uani 1 1 d . . . . . H14 H 1.0671 0.5209 0.0822 0.087 Uiso 1 1 calc R . . . . C15 C 0.6595(6) 0.6104(4) 0.12842(13) 0.0473(8) Uani 1 1 d . . . . . C16 C 0.7091(8) 0.7333(4) 0.15313(16) 0.0686(12) Uani 1 1 d . . . . . H16 H 0.8023 0.7242 0.1809 0.082 Uiso 1 1 calc R . . . . C17 C 0.6258(10) 0.8678(5) 0.1380(2) 0.0880(16) Uani 1 1 d . . . . . H17 H 0.6629 0.9485 0.1555 0.106 Uiso 1 1 calc R . . . . C18 C 0.4897(9) 0.8850(6) 0.0979(2) 0.0880(15) Uani 1 1 d . . . . . H18 H 0.4311 0.9769 0.0883 0.106 Uiso 1 1 calc R . . . . C19 C 0.4382(8) 0.7662(6) 0.07142(19) 0.0842(15) Uani 1 1 d . . . . . H19 H 0.3448 0.7772 0.0437 0.101 Uiso 1 1 calc R . . . . C20 C 0.5267(7) 0.6295(4) 0.08632(15) 0.0620(10) Uani 1 1 d . . . . . H20 H 0.4958 0.5497 0.0676 0.074 Uiso 1 1 calc R . . . . C21 C 0.5709(6) 0.4931(3) 0.23194(12) 0.0443(8) Uani 1 1 d . . . . . C22 C 0.3558(6) 0.5399(4) 0.22087(14) 0.0512(9) Uani 1 1 d . . . . . C23 C 0.2230(6) 0.6116(4) 0.25682(15) 0.0566(9) Uani 1 1 d . . . . . C24 C 0.3027(6) 0.6397(4) 0.30483(14) 0.0533(9) Uani 1 1 d . . . . . C25 C 0.5197(6) 0.5960(4) 0.31657(13) 0.0484(8) Uani 1 1 d . . . . . C26 C 0.6490(6) 0.5214(4) 0.28024(13) 0.0481(8) Uani 1 1 d . . . . . C27 C 0.6093(7) 0.6250(4) 0.36615(15) 0.0580(10) Uani 1 1 d . . . . . H27 H 0.7549 0.5987 0.3720 0.070 Uiso 1 1 calc R . . . . C28 C 0.5900(7) 0.7130(5) 0.44933(14) 0.0618(11) Uani 1 1 d . . . . . C29 C 0.8021(18) 0.7416(12) 0.4539(4) 0.103(3) Uani 0.586(4) 1 d . U P A 1 H29 H 0.8929 0.7407 0.4248 0.123 Uiso 0.586(4) 1 calc R . P A 1 C29A C 0.721(3) 0.6294(19) 0.4757(5) 0.103(3) Uani 0.414(4) 1 d . . P A 2 H29A H 0.7628 0.5404 0.4619 0.123 Uiso 0.414(4) 1 calc R . P A 2 C30 C 0.8847(17) 0.7722(12) 0.5012(3) 0.101(2) Uani 0.586(4) 1 d . U P A 1 H30 H 1.0308 0.7904 0.5030 0.121 Uiso 0.586(4) 1 calc R . P A 1 C30A C 0.808(2) 0.6589(19) 0.5241(5) 0.101(2) Uani 0.414(4) 1 d . . P A 2 H30A H 0.9046 0.5906 0.5398 0.121 Uiso 0.414(4) 1 calc R . P A 2 C31 C 0.7571(7) 0.7767(5) 0.54639(15) 0.0632(11) Uani 1 1 d . . . . . C32 C 0.5600(14) 0.7279(10) 0.5412(3) 0.0813(18) Uani 0.586(4) 1 d . U P A 1 H32 H 0.4763 0.7129 0.5709 0.098 Uiso 0.586(4) 1 calc R . P A 1 C32A C 0.5981(19) 0.8758(15) 0.5214(4) 0.0813(18) Uani 0.414(4) 1 d . . P A 2 H32A H 0.5475 0.9596 0.5377 0.098 Uiso 0.414(4) 1 calc R . P A 2 C33 C 0.4710(14) 0.6977(10) 0.4935(3) 0.0824(19) Uani 0.586(4) 1 d . U P A 1 H33 H 0.3305 0.6672 0.4922 0.099 Uiso 0.586(4) 1 calc R . P A 1 C33A C 0.5218(19) 0.8471(15) 0.4741(4) 0.0824(19) Uani 0.414(4) 1 d . . P A 2 H33A H 0.4254 0.9139 0.4576 0.099 Uiso 0.414(4) 1 calc R . P A 2 C34 C 0.9895(15) 0.9400(9) 0.5917(3) 0.148(3) Uani 1 1 d . U . . . H34A H 1.0974 0.9205 0.5652 0.222 Uiso 1 1 calc GR . . . . H34B H 1.0597 0.9542 0.6236 0.222 Uiso 1 1 calc GR . . . . H34C H 0.9020 1.0259 0.5821 0.222 Uiso 1 1 calc GR . . . . C35 C 0.8462(8) 0.8124(6) 0.59808(16) 0.0803(13) Uani 1 1 d . U . . . C36 C 0.976(3) 0.6917(12) 0.6208(4) 0.232(6) Uani 1 1 d . U . . . H36A H 0.8862 0.6122 0.6281 0.348 Uiso 1 1 calc GR . . . . H36C H 1.0374 0.7207 0.6522 0.348 Uiso 1 1 calc GR . . . . H36B H 1.0908 0.6622 0.5972 0.348 Uiso 1 1 calc GR . . . . C37 C 0.6702(16) 0.8647(15) 0.6343(3) 0.206(5) Uani 1 1 d . U . . . H37C H 0.5618 0.7947 0.6373 0.310 Uiso 1 1 calc GR . . . . H37A H 0.6053 0.9554 0.6213 0.310 Uiso 1 1 calc GR . . . . H37B H 0.7301 0.8778 0.6675 0.310 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 0.0673(18) 0.100(2) 0.0642(18) -0.0217(17) 0.0026(15) 0.0235(17) N1 0.073(2) 0.079(2) 0.0461(18) -0.0174(16) -0.0005(16) 0.0056(18) C1 0.066(2) 0.0481(19) 0.0381(18) -0.0105(15) -0.0102(16) 0.0039(17) C2 0.098(3) 0.052(2) 0.049(2) 0.0011(17) 0.001(2) 0.004(2) C3 0.153(5) 0.052(3) 0.058(3) 0.001(2) -0.008(3) 0.008(3) C4 0.165(6) 0.055(3) 0.072(3) -0.013(2) -0.043(4) 0.033(4) C5 0.100(4) 0.076(3) 0.096(4) -0.032(3) -0.038(3) 0.036(3) C6 0.073(3) 0.066(3) 0.070(3) -0.020(2) -0.015(2) 0.013(2) C7 0.0495(19) 0.0457(19) 0.0403(18) -0.0040(14) -0.0062(15) -0.0057(15) C8 0.052(2) 0.0475(19) 0.0442(19) -0.0054(15) -0.0053(15) -0.0127(15) C9 0.061(2) 0.052(2) 0.0394(18) -0.0074(15) -0.0020(16) -0.0110(17) C10 0.093(3) 0.059(2) 0.050(2) -0.0113(18) 0.003(2) -0.020(2) C11 0.117(4) 0.067(3) 0.067(3) -0.028(2) 0.003(3) -0.018(3) C12 0.102(4) 0.097(4) 0.064(3) -0.037(3) 0.007(3) 0.004(3) C13 0.088(3) 0.108(4) 0.078(3) -0.033(3) 0.031(3) -0.021(3) C14 0.082(3) 0.073(3) 0.067(3) -0.020(2) 0.016(2) -0.027(2) C15 0.053(2) 0.0502(19) 0.0391(17) 0.0012(14) 0.0011(15) -0.0114(16) C16 0.097(3) 0.052(2) 0.059(2) 0.0028(18) -0.024(2) -0.016(2) C17 0.133(5) 0.052(3) 0.080(3) 0.007(2) -0.025(3) -0.018(3) C18 0.105(4) 0.065(3) 0.092(4) 0.021(3) -0.008(3) -0.001(3) C19 0.080(3) 0.099(4) 0.073(3) 0.021(3) -0.024(2) -0.007(3) C20 0.068(2) 0.063(2) 0.056(2) -0.0002(18) -0.0118(19) -0.012(2) C21 0.0525(19) 0.0399(17) 0.0405(17) 0.0000(13) -0.0044(15) -0.0029(15) C22 0.057(2) 0.049(2) 0.048(2) 0.0009(15) -0.0071(16) -0.0017(16) C23 0.051(2) 0.060(2) 0.058(2) -0.0016(18) -0.0041(17) 0.0027(17) C24 0.056(2) 0.054(2) 0.049(2) -0.0040(16) 0.0016(17) 0.0065(17) C25 0.054(2) 0.0482(19) 0.0426(18) -0.0006(15) -0.0007(15) 0.0006(16) C26 0.052(2) 0.051(2) 0.0408(18) -0.0046(15) -0.0021(15) -0.0005(16) C27 0.058(2) 0.063(2) 0.052(2) -0.0083(18) -0.0035(18) 0.0053(18) C28 0.072(3) 0.071(3) 0.041(2) -0.0086(18) -0.0054(19) 0.008(2) C29 0.113(5) 0.136(6) 0.063(4) -0.037(4) 0.014(4) -0.027(5) C29A 0.113(5) 0.136(6) 0.063(4) -0.037(4) 0.014(4) -0.027(5) C30 0.100(5) 0.141(6) 0.067(4) -0.028(4) -0.002(4) -0.028(4) C30A 0.100(5) 0.141(6) 0.067(4) -0.028(4) -0.002(4) -0.028(4) C31 0.079(3) 0.069(3) 0.042(2) -0.0054(18) -0.0008(19) -0.005(2) C32 0.084(4) 0.108(5) 0.053(3) -0.017(3) 0.004(3) -0.007(4) C32A 0.084(4) 0.108(5) 0.053(3) -0.017(3) 0.004(3) -0.007(4) C33 0.074(4) 0.113(5) 0.061(4) -0.017(3) 0.001(3) -0.006(4) C33A 0.074(4) 0.113(5) 0.061(4) -0.017(3) 0.001(3) -0.006(4) C34 0.182(7) 0.168(6) 0.104(5) -0.014(4) -0.035(5) -0.078(5) C35 0.092(3) 0.103(3) 0.045(2) -0.003(2) -0.008(2) 0.001(2) C36 0.365(13) 0.191(9) 0.139(7) -0.007(6) -0.147(8) 0.042(9) C37 0.161(7) 0.377(13) 0.086(5) -0.101(7) -0.017(5) -0.001(8) 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' 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C27 N1 C28 121.2(4) . . ? C2 C1 C7 118.8(3) . . ? C6 C1 C2 118.5(4) . . ? C6 C1 C7 122.6(4) . . ? C3 C2 C1 120.5(5) . . ? C4 C3 C2 120.8(5) . . ? C3 C4 C5 120.3(5) . . ? C4 C5 C6 120.2(5) . . ? C1 C6 C5 119.7(5) . . ? C8 C7 C1 124.3(3) . . ? C8 C7 C21 121.5(3) . . ? C21 C7 C1 114.2(3) . . ? C7 C8 C9 122.9(3) . . ? C7 C8 C15 121.9(3) . . ? C15 C8 C9 115.2(3) . . ? C10 C9 C8 122.0(3) . . ? C10 C9 C14 118.0(4) . . ? C14 C9 C8 120.0(3) . . ? C11 C10 C9 121.0(4) . . ? C10 C11 C12 120.8(4) . . ? C13 C12 C11 119.0(4) . . ? C12 C13 C14 120.4(5) . . ? C13 C14 C9 120.7(4) . . ? C16 C15 C8 122.9(3) . . ? C16 C15 C20 117.0(3) . . ? C20 C15 C8 120.1(3) . . ? C17 C16 C15 122.0(4) . . ? C18 C17 C16 120.6(4) . . ? C17 C18 C19 119.7(5) . . ? C18 C19 C20 119.5(4) . . ? C15 C20 C19 121.1(4) . . ? C22 C21 C7 121.4(3) . . ? C26 C21 C7 120.5(3) . . ? C26 C21 C22 118.0(3) . . ? C23 C22 C21 121.5(3) . . ? C22 C23 C24 120.1(3) . . ? O1 C24 C23 118.5(3) . . ? O1 C24 C25 122.0(3) . . ? C23 C24 C25 119.5(3) . . ? C24 C25 C27 121.1(3) . . ? C26 C25 C24 119.4(3) . . ? C26 C25 C27 119.5(3) . . ? C21 C26 C25 121.5(3) . . ? N1 C27 C25 122.6(4) . . ? N1 C28 C33A 118.3(6) . . ? C29 C28 N1 122.9(5) . . ? C29A C28 N1 127.4(7) . . ? C29A C28 C33A 114.2(8) . . ? C33 C28 N1 119.4(5) . . ? C33 C28 C29 117.4(6) . . ? C28 C29 C30 120.8(8) . . ? C28 C29A C30A 126.4(14) . . ? C29 C30 C31 122.6(9) . . ? C31 C30A C29A 121.3(15) . . ? C30 C31 C35 122.8(5) . . ? C30A C31 C32A 116.9(9) . . ? C30A C31 C35 123.1(8) . . ? C32 C31 C30 113.8(6) . . ? C32 C31 C35 122.8(5) . . ? C32A C31 C35 119.9(6) . . ? C31 C32 C33 123.9(7) . . ? C33A C32A C31 120.4(11) . . ? C28 C33 C32 120.1(7) . . ? C32A C33A C28 120.5(11) . . ? C31 C35 C34 110.0(4) . . ? C36 C35 C31 112.1(5) . . ? C36 C35 C34 107.7(8) . . ? C36 C35 C37 111.2(8) . . ? C37 C35 C31 111.6(5) . . ? C37 C35 C34 103.9(7) . . ? 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 C24 1.341(4) . ? N1 C27 1.264(5) . ? N1 C28 1.414(5) . ? C1 C2 1.391(6) . ? C1 C6 1.384(6) . ? C1 C7 1.502(5) . ? C2 C3 1.387(6) . ? C3 C4 1.338(9) . ? C4 C5 1.378(9) . ? C5 C6 1.399(7) . ? C7 C8 1.343(5) . ? C7 C21 1.499(5) . ? C8 C9 1.500(5) . ? C8 C15 1.491(5) . ? C9 C10 1.375(5) . ? C9 C14 1.382(6) . ? C10 C11 1.365(6) . ? C11 C12 1.369(7) . ? C12 C13 1.369(7) . ? C13 C14 1.374(6) . ? C15 C16 1.379(5) . ? C15 C20 1.380(5) . ? C16 C17 1.364(6) . ? C17 C18 1.350(7) . ? C18 C19 1.374(7) . ? C19 C20 1.391(6) . ? C21 C22 1.402(5) . ? C21 C26 1.392(5) . ? C22 C23 1.388(5) . ? C23 C24 1.389(5) . ? C24 C25 1.411(5) . ? C25 C26 1.396(5) . ? C25 C27 1.452(5) . ? C28 C29 1.360(11) . ? C28 C29A 1.274(17) . ? C28 C33 1.357(9) . ? C28 C33A 1.451(13) . ? C29 C30 1.385(13) . ? C29A C30A 1.420(18) . ? C30 C31 1.401(10) . ? C30A C31 1.270(16) . ? C31 C32 1.334(10) . ? C31 C32A 1.448(13) . ? C31 C35 1.516(6) . ? C32 C33 1.411(11) . ? C32A C33A 1.366(15) . ? C34 C35 1.521(9) . ? C35 C36 1.449(10) . ? C35 C37 1.490(9) . ? 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 O1 H1 N1 0.82 1.90 2.622(5) 146.0 . 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 O1 C24 C25 C26 177.7(4) . . . . ? O1 C24 C25 C27 -1.1(6) . . . . ? N1 C28 C29 C30 178.5(8) . . . . ? N1 C28 C29A C30A -178.4(11) . . . . ? N1 C28 C33 C32 -178.9(7) . . . . ? N1 C28 C33A C32A 176.5(9) . . . . ? C1 C2 C3 C4 -0.3(7) . . . . ? C1 C7 C8 C9 6.0(5) . . . . ? C1 C7 C8 C15 -175.9(3) . . . . ? C1 C7 C21 C22 -123.2(3) . . . . ? C1 C7 C21 C26 54.6(4) . . . . ? C2 C1 C6 C5 0.6(5) . . . . ? C2 C1 C7 C8 -136.7(4) . . . . ? C2 C1 C7 C21 40.5(4) . . . . ? C2 C3 C4 C5 1.1(8) . . . . ? C3 C4 C5 C6 -1.0(7) . . . . ? C4 C5 C6 C1 0.2(6) . . . . ? C6 C1 C2 C3 -0.5(6) . . . . ? C6 C1 C7 C8 43.2(5) . . . . ? C6 C1 C7 C21 -139.6(3) . . . . ? C7 C1 C2 C3 179.4(4) . . . . ? C7 C1 C6 C5 -179.3(3) . . . . ? C7 C8 C9 C10 53.7(5) . . . . ? C7 C8 C9 C14 -128.1(4) . . . . ? C7 C8 C15 C16 54.6(5) . . . . ? C7 C8 C15 C20 -125.1(4) . . . . ? C7 C21 C22 C23 177.5(3) . . . . ? C7 C21 C26 C25 -178.9(3) . . . . ? C8 C7 C21 C22 54.0(5) . . . . ? C8 C7 C21 C26 -128.1(4) . . . . ? C8 C9 C10 C11 -179.7(4) . . . . ? C8 C9 C14 C13 179.0(4) . . . . ? C8 C15 C16 C17 -177.6(4) . . . . ? C8 C15 C20 C19 176.4(4) . . . . ? C9 C8 C15 C16 -127.1(4) . . . . ? C9 C8 C15 C20 53.2(4) . . . . ? C9 C10 C11 C12 0.0(8) . . . . ? C10 C9 C14 C13 -2.7(7) . . . . ? C10 C11 C12 C13 -1.4(8) . . . . ? C11 C12 C13 C14 0.7(9) . . . . ? C12 C13 C14 C9 1.4(8) . . . . ? C14 C9 C10 C11 2.0(6) . . . . ? C15 C8 C9 C10 -124.6(4) . . . . ? C15 C8 C9 C14 53.6(5) . . . . ? C15 C16 C17 C18 0.1(8) . . . . ? C16 C15 C20 C19 -3.3(6) . . . . ? C16 C17 C18 C19 -1.3(9) . . . . ? C17 C18 C19 C20 0.1(8) . . . . ? C18 C19 C20 C15 2.3(7) . . . . ? C20 C15 C16 C17 2.2(7) . . . . ? C21 C7 C8 C9 -171.0(3) . . . . ? C21 C7 C8 C15 7.1(5) . . . . ? C21 C22 C23 C24 0.6(6) . . . . ? C22 C21 C26 C25 -1.0(5) . . . . ? C22 C23 C24 O1 -179.0(4) . . . . ? C22 C23 C24 C25 0.6(6) . . . . ? C23 C24 C25 C26 -1.9(5) . . . . ? C23 C24 C25 C27 179.3(4) . . . . ? C24 C25 C26 C21 2.1(5) . . . . ? C24 C25 C27 N1 2.9(6) . . . . ? C26 C21 C22 C23 -0.4(5) . . . . ? C26 C25 C27 N1 -175.9(4) . . . . ? C27 N1 C28 C29 30.3(9) . . . . ? C27 N1 C28 C29A -42.9(11) . . . . ? C27 N1 C28 C33 -143.0(6) . . . . ? C27 N1 C28 C33A 141.8(7) . . . . ? C27 C25 C26 C21 -179.1(3) . . . . ? C28 N1 C27 C25 -179.2(4) . . . . ? C28 C29 C30 C31 -0.6(17) . . . . ? C28 C29A C30A C31 1(2) . . . . ? C29 C28 C33 C32 7.4(12) . . . . ? C29 C30 C31 C32 9.6(14) . . . . ? C29 C30 C31 C35 -179.0(9) . . . . ? C29A C28 C33A C32A 0.6(15) . . . . ? C29A C30A C31 C32A 3.0(18) . . . . ? C29A C30A C31 C35 179.9(10) . . . . ? C30 C31 C32 C33 -10.4(12) . . . . ? C30 C31 C35 C34 43.5(9) . . . . ? C30 C31 C35 C36 -76.2(10) . . . . ? C30 C31 C35 C37 158.3(9) . . . . ? C30A C31 C32A C33A -5.1(15) . . . . ? C30A C31 C35 C34 113.9(10) . . . . ? C30A C31 C35 C36 -5.9(12) . . . . ? C30A C31 C35 C37 -131.4(11) . . . . ? C31 C32 C33 C28 2.3(14) . . . . ? C31 C32A C33A C28 3.4(17) . . . . ? C32 C31 C35 C34 -145.8(7) . . . . ? C32 C31 C35 C36 94.4(10) . . . . ? C32 C31 C35 C37 -31.1(10) . . . . ? C32A C31 C35 C34 -69.3(8) . . . . ? C32A C31 C35 C36 171.0(10) . . . . ? C32A C31 C35 C37 45.5(10) . . . . ? C33 C28 C29 C30 -8.1(14) . . . . ? C33A C28 C29A C30A -2.9(18) . . . . ? C35 C31 C32 C33 178.2(7) . . . . ? C35 C31 C32A C33A 177.9(9) . . . . ?