#------------------------------------------------------------------------------ #$Date: 2026-06-04 10:23:32 +0100 (Thu, 04 Jun 2026) $ #$Revision: 306202 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577360.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_1577360 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 'C33 H24 N2 O3' _chemical_formula_sum 'C33 H24 N2 O3' _chemical_formula_weight 496.54 _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 91.759(4) _cell_angle_beta 93.335(4) _cell_angle_gamma 102.376(4) _cell_formula_units_Z 2 _cell_length_a 5.5572(7) _cell_length_b 9.3767(13) _cell_length_c 25.710(3) _cell_measurement_reflns_used 1589 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 22.75 _cell_measurement_theta_min 3.33 _cell_volume 1305.1(3) _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 0.991 _diffrn_measured_fraction_theta_max 0.974 _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 0.1147 _diffrn_reflns_av_unetI/netI 0.2272 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.974 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 14067 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.974 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.283 _diffrn_reflns_theta_min 2.677 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_crystal_density_diffrn 1.264 _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.223 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.059 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 344 _refine_ls_number_reflns 6324 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.2894 _refine_ls_R_factor_gt 0.1406 _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^)+3.7296P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1886 _refine_ls_wR_factor_ref 0.2362 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2596 _reflns_number_total 6324 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc00735j2.cif _cod_data_source_block aaa_CCDC1 _cod_database_code 1577360 _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 0.992 _shelx_estimated_absorpt_t_min 0.984 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All O(H) groups 2.a Aromatic/amide H refined with riding coordinates: C12(H12), C11(H11), C10(H10), C26(H26), C27(H27), C29(H29), C30(H30), C33(H33), C32(H32), C22(H22), C23(H23), C6(H6), C5(H5), C4(H4), C3(H3), C2(H2), C13(H13), C14(H14), C20(H20), C19(H19), C18(H18), C17(H17), C16(H16) 2.b 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 5.5572 9.3767 25.7098 91.759 93.335 102.376 ZERR 2 0.0007 0.0013 0.0033 0.004 0.004 0.004 LATT 1 SFAC C H N O UNIT 66 48 4 6 EQIV $1 -X,1-Y,1-Z EQIV $2 2-X,-Y,1-Z L.S. 4 PLAN -5 SIZE 0.1 0.12 0.2 TEMP 0 HTAB O1 N1 HTAB C29 O1_$1 HTAB C32 O3_$2 fmap 2 acta MERG 2 REM REM REM WGHT 0.000000 3.729600 FVAR 0.59075 O2 4 0.661646 0.092892 0.370895 11.00000 0.10931 0.17366 = 0.03172 -0.02916 -0.00811 0.05577 O1 4 0.030871 0.541906 0.588245 11.00000 0.07409 0.05751 = 0.03287 0.00723 -0.00445 0.03079 AFIX 147 H1 2 0.110041 0.495198 0.571126 11.00000 -1.50000 AFIX 0 N1 3 0.333616 0.373634 0.572189 11.00000 0.03792 0.03814 = 0.03308 0.00993 0.00613 0.00806 O3 4 0.905564 0.022879 0.426446 11.00000 0.09010 0.09909 = 0.06233 -0.00939 0.01675 0.04173 C12 1 0.299753 0.247534 0.982410 11.00000 0.11760 0.10704 = 0.02068 0.00307 0.00111 0.04732 AFIX 43 H12 2 0.332603 0.228335 1.017072 11.00000 -1.20000 AFIX 0 C11 1 0.075016 0.187270 0.957467 11.00000 0.10638 0.06736 = 0.04847 0.01793 0.01674 0.01996 AFIX 43 H11 2 -0.044860 0.125426 0.974855 11.00000 -1.20000 AFIX 0 C10 1 0.027626 0.218920 0.906365 11.00000 0.05984 0.05366 = 0.03096 0.01148 0.01090 0.00393 AFIX 43 H10 2 -0.124982 0.177065 0.889524 11.00000 -1.20000 AFIX 0 C9 1 0.200640 0.311053 0.879550 11.00000 0.02661 0.03380 = 0.03376 0.00000 0.00157 0.00824 C8 1 0.144267 0.339904 0.823856 11.00000 0.02458 0.02642 = 0.03183 -0.00225 0.00553 0.00302 C7 1 0.188929 0.472197 0.804615 11.00000 0.02886 0.03608 = 0.03134 0.00642 0.00891 0.01205 C21 1 0.157303 0.491200 0.747172 11.00000 0.02964 0.01832 = 0.03561 0.00367 0.00876 -0.00249 C26 1 0.270111 0.423334 0.710514 11.00000 0.03991 0.02726 = 0.03806 0.00502 0.00609 0.01433 AFIX 43 H26 2 0.376168 0.364993 0.722221 11.00000 -1.20000 AFIX 0 C25 1 0.235598 0.436447 0.657069 11.00000 0.02921 0.03118 = 0.03168 0.00378 0.00837 0.00130 C27 1 0.360638 0.360394 0.621364 11.00000 0.04439 0.03581 = 0.04320 0.01240 0.00459 0.01443 AFIX 43 H27 2 0.462255 0.300944 0.634311 11.00000 -1.20000 AFIX 0 C28 1 0.450454 0.300166 0.535178 11.00000 0.03071 0.03236 = 0.02999 0.00515 0.00424 0.00311 C29 1 0.363123 0.301945 0.483995 11.00000 0.04907 0.05694 = 0.04296 0.01152 -0.00106 0.01482 AFIX 43 H29 2 0.237980 0.351127 0.476035 11.00000 -1.20000 AFIX 0 C30 1 0.457210 0.232198 0.444032 11.00000 0.03800 0.06674 = 0.02532 0.00689 0.00080 -0.00611 AFIX 43 H30 2 0.397148 0.232618 0.409523 11.00000 -1.20000 AFIX 0 C31 1 0.643920 0.162297 0.457959 11.00000 0.03687 0.04489 = 0.03111 -0.01159 0.00024 -0.00692 N2 3 0.742014 0.087507 0.414855 11.00000 0.05888 0.05712 = 0.03605 -0.01035 0.00792 -0.00363 C33 1 0.639877 0.228090 0.546131 11.00000 0.03870 0.04715 = 0.02963 0.00251 -0.00436 0.00888 AFIX 43 H33 2 0.701410 0.226120 0.580461 11.00000 -1.20000 AFIX 0 C32 1 0.737346 0.160164 0.507511 11.00000 0.03166 0.05113 = 0.03897 0.00268 0.00995 0.01221 AFIX 43 H32 2 0.865755 0.113242 0.515144 11.00000 -1.20000 AFIX 0 C22 1 0.002831 0.578233 0.727646 11.00000 0.04838 0.03270 = 0.04585 -0.00199 0.00930 0.01557 AFIX 43 H22 2 -0.074023 0.628296 0.751100 11.00000 -1.20000 AFIX 0 C23 1 -0.041429 0.593600 0.675100 11.00000 0.05739 0.04053 = 0.05479 0.00365 -0.00327 0.03075 AFIX 43 H23 2 -0.150695 0.650332 0.663701 11.00000 -1.20000 AFIX 0 C24 1 0.076629 0.524654 0.639255 11.00000 0.04016 0.03433 = 0.03500 0.00360 -0.00159 0.00779 C1 1 0.267863 0.613600 0.836210 11.00000 0.02805 0.03250 = 0.03311 -0.00223 0.00183 0.01097 C6 1 0.470878 0.718194 0.824034 11.00000 0.04422 0.04075 = 0.05676 -0.00635 0.02265 0.00276 AFIX 43 H6 2 0.563699 0.699732 0.796646 11.00000 -1.20000 AFIX 0 C5 1 0.535919 0.849441 0.852309 11.00000 0.06031 0.03923 = 0.07052 -0.01123 0.00342 -0.00310 AFIX 43 H5 2 0.674119 0.918335 0.844196 11.00000 -1.20000 AFIX 0 C4 1 0.400581 0.879262 0.891849 11.00000 0.07232 0.04241 = 0.04486 -0.01609 -0.00955 0.00779 AFIX 43 H4 2 0.445963 0.968522 0.910502 11.00000 -1.20000 AFIX 0 C3 1 0.201636 0.780677 0.904183 11.00000 0.07080 0.05274 = 0.04722 -0.01623 0.01800 0.01044 AFIX 43 H3 2 0.109256 0.802045 0.931246 11.00000 -1.20000 AFIX 0 C2 1 0.132347 0.645666 0.876489 11.00000 0.05170 0.03582 = 0.05110 -0.00660 0.02120 -0.00280 AFIX 43 H2 2 -0.005393 0.577528 0.885303 11.00000 -1.20000 AFIX 0 C13 1 0.474632 0.335617 0.956209 11.00000 0.07662 0.09489 = 0.05967 -0.00667 -0.03257 0.03347 AFIX 43 H13 2 0.628568 0.374567 0.972996 11.00000 -1.20000 AFIX 0 C14 1 0.427589 0.368540 0.904781 11.00000 0.04183 0.06656 = 0.05213 0.00042 -0.00334 0.00529 AFIX 43 H14 2 0.549181 0.429273 0.887457 11.00000 -1.20000 AFIX 0 C15 1 0.030217 0.206217 0.790335 11.00000 0.02675 0.02172 = 0.03085 0.00830 0.00535 0.00813 C20 1 -0.190954 0.197666 0.760881 11.00000 0.04041 0.02765 = 0.04425 -0.00518 -0.00507 0.01248 AFIX 43 H20 2 -0.273028 0.273910 0.763717 11.00000 -1.20000 AFIX 0 C19 1 -0.290590 0.080183 0.727914 11.00000 0.03864 0.05896 = 0.04804 -0.00973 -0.01468 0.00278 AFIX 43 H19 2 -0.438890 0.076379 0.708636 11.00000 -1.20000 AFIX 0 C18 1 -0.168033 -0.033345 0.723526 11.00000 0.06797 0.05573 = 0.05813 -0.02689 0.00105 0.00658 AFIX 43 H18 2 -0.231182 -0.112815 0.700522 11.00000 -1.20000 AFIX 0 C17 1 0.046757 -0.027697 0.753305 11.00000 0.06669 0.02244 = 0.08815 -0.00744 0.01229 0.01096 AFIX 43 H17 2 0.128422 -0.104169 0.750643 11.00000 -1.20000 AFIX 0 C16 1 0.141925 0.089016 0.786814 11.00000 0.03517 0.02422 = 0.05498 0.00005 0.00039 0.01138 AFIX 43 H16 2 0.284671 0.089401 0.807628 11.00000 -1.20000 AFIX 0 HKLF 4 REM AAA_a.res in P-1 REM R1 = 0.1406 for 2596 Fo > 4sig(Fo) and 0.2894 for all 6324 data REM 344 parameters refined using 0 restraints END WGHT 0.0000 3.7297 REM Highest difference peak 0.223, deepest hole -0.308, 1-sigma level 0.059 Q1 1 0.2913 0.5602 0.2251 11.00000 0.05 0.22 Q2 1 0.5749 0.4359 0.5067 11.00000 0.05 0.22 Q3 1 -0.0231 0.4589 0.8767 11.00000 0.05 0.21 Q4 1 0.1353 -0.0804 0.6976 11.00000 0.05 0.21 Q5 1 0.2604 0.4638 0.5806 11.00000 0.05 0.21 ; _shelx_res_checksum 51246 _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 O2 O 0.6616(11) 0.0929(7) 0.37089(19) 0.102(2) Uani 1 1 d . . . . . O1 O 0.0309(9) 0.5419(5) 0.58825(15) 0.0525(13) Uani 1 1 d . . . . . H1 H 0.1100 0.4952 0.5711 0.079 Uiso 1 1 calc GR . . . . N1 N 0.3336(8) 0.3736(5) 0.57219(18) 0.0361(12) Uani 1 1 d . . . . . O3 O 0.9056(11) 0.0229(6) 0.4264(2) 0.0805(17) Uani 1 1 d . . . . . C12 C 0.2998(19) 0.2475(10) 0.9824(3) 0.078(3) Uani 1 1 d . . . . . H12 H 0.3326 0.2283 1.0171 0.094 Uiso 1 1 calc R . . . . C11 C 0.0750(17) 0.1873(8) 0.9575(3) 0.073(2) Uani 1 1 d . . . . . H11 H -0.0449 0.1254 0.9749 0.088 Uiso 1 1 calc R . . . . C10 C 0.0276(12) 0.2189(7) 0.9064(2) 0.0489(18) Uani 1 1 d . . . . . H10 H -0.1250 0.1771 0.8895 0.059 Uiso 1 1 calc R . . . . C9 C 0.2006(10) 0.3111(6) 0.8796(2) 0.0312(13) Uani 1 1 d . . . . . C8 C 0.1443(9) 0.3399(6) 0.8239(2) 0.0279(13) Uani 1 1 d . . . . . C7 C 0.1889(10) 0.4722(6) 0.8046(2) 0.0310(14) Uani 1 1 d . . . . . C21 C 0.1573(10) 0.4912(5) 0.7472(2) 0.0287(13) Uani 1 1 d . . . . . C26 C 0.2701(10) 0.4233(6) 0.7105(2) 0.0338(14) Uani 1 1 d . . . . . H26 H 0.3762 0.3650 0.7222 0.041 Uiso 1 1 calc R . . . . C25 C 0.2356(10) 0.4364(6) 0.6571(2) 0.0312(13) Uani 1 1 d . . . . . C27 C 0.3606(11) 0.3604(6) 0.6214(2) 0.0400(15) Uani 1 1 d . . . . . H27 H 0.4623 0.3009 0.6343 0.048 Uiso 1 1 calc R . . . . C28 C 0.4505(10) 0.3002(6) 0.5352(2) 0.0314(13) Uani 1 1 d . . . . . C29 C 0.3631(12) 0.3019(7) 0.4840(2) 0.0491(17) Uani 1 1 d . . . . . H29 H 0.2380 0.3511 0.4760 0.059 Uiso 1 1 calc R . . . . C30 C 0.4572(11) 0.2322(7) 0.4440(2) 0.0459(17) Uani 1 1 d . . . . . H30 H 0.3971 0.2326 0.4095 0.055 Uiso 1 1 calc R . . . . C31 C 0.6439(11) 0.1623(7) 0.4580(2) 0.0404(15) Uani 1 1 d . . . . . N2 N 0.7420(11) 0.0875(6) 0.4149(2) 0.0532(15) Uani 1 1 d . . . . . C33 C 0.6399(10) 0.2281(6) 0.5461(2) 0.0388(15) Uani 1 1 d . . . . . H33 H 0.7014 0.2261 0.5805 0.047 Uiso 1 1 calc R . . . . C32 C 0.7373(10) 0.1602(6) 0.5075(2) 0.0398(15) Uani 1 1 d . . . . . H32 H 0.8658 0.1132 0.5151 0.048 Uiso 1 1 calc R . . . . C22 C 0.0028(11) 0.5782(6) 0.7276(2) 0.0411(16) Uani 1 1 d . . . . . H22 H -0.0740 0.6283 0.7511 0.049 Uiso 1 1 calc R . . . . C23 C -0.0414(12) 0.5936(7) 0.6751(2) 0.0481(17) Uani 1 1 d . . . . . H23 H -0.1507 0.6503 0.6637 0.058 Uiso 1 1 calc R . . . . C24 C 0.0766(11) 0.5247(6) 0.6393(2) 0.0367(14) Uani 1 1 d . . . . . C1 C 0.2679(10) 0.6136(6) 0.8362(2) 0.0306(13) Uani 1 1 d . . . . . C6 C 0.4709(11) 0.7182(7) 0.8240(2) 0.0476(17) Uani 1 1 d . . . . . H6 H 0.5637 0.6997 0.7966 0.057 Uiso 1 1 calc R . . . . C5 C 0.5359(13) 0.8494(7) 0.8523(3) 0.059(2) Uani 1 1 d . . . . . H5 H 0.6741 0.9183 0.8442 0.071 Uiso 1 1 calc R . . . . C4 C 0.4006(14) 0.8793(7) 0.8918(2) 0.0548(19) Uani 1 1 d . . . . . H4 H 0.4460 0.9685 0.9105 0.066 Uiso 1 1 calc R . . . . C3 C 0.2016(14) 0.7807(8) 0.9042(3) 0.0572(19) Uani 1 1 d . . . . . H3 H 0.1093 0.8020 0.9312 0.069 Uiso 1 1 calc R . . . . C2 C 0.1323(12) 0.6457(6) 0.8765(2) 0.0475(17) Uani 1 1 d . . . . . H2 H -0.0054 0.5775 0.8853 0.057 Uiso 1 1 calc R . . . . C13 C 0.4746(16) 0.3356(9) 0.9562(3) 0.077(3) Uani 1 1 d . . . . . H13 H 0.6286 0.3746 0.9730 0.092 Uiso 1 1 calc R . . . . C14 C 0.4276(12) 0.3685(7) 0.9048(3) 0.0548(18) Uani 1 1 d . . . . . H14 H 0.5492 0.4293 0.8875 0.066 Uiso 1 1 calc R . . . . C15 C 0.0302(9) 0.2062(5) 0.79033(19) 0.0257(12) Uani 1 1 d . . . . . C20 C -0.1910(11) 0.1977(6) 0.7609(2) 0.0371(15) Uani 1 1 d . . . . . H20 H -0.2730 0.2739 0.7637 0.045 Uiso 1 1 calc R . . . . C19 C -0.2906(11) 0.0802(7) 0.7279(2) 0.0507(18) Uani 1 1 d . . . . . H19 H -0.4389 0.0764 0.7086 0.061 Uiso 1 1 calc R . . . . C18 C -0.1680(14) -0.0333(8) 0.7235(3) 0.062(2) Uani 1 1 d . . . . . H18 H -0.2312 -0.1128 0.7005 0.075 Uiso 1 1 calc R . . . . C17 C 0.0468(13) -0.0277(7) 0.7533(3) 0.059(2) Uani 1 1 d . . . . . H17 H 0.1284 -0.1042 0.7506 0.071 Uiso 1 1 calc R . . . . C16 C 0.1419(11) 0.0890(6) 0.7868(2) 0.0375(15) Uani 1 1 d . . . . . H16 H 0.2847 0.0894 0.8076 0.045 Uiso 1 1 calc R . . . . 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 O2 0.109(5) 0.174(7) 0.032(3) -0.029(3) -0.008(3) 0.056(5) O1 0.074(4) 0.058(3) 0.033(2) 0.007(2) -0.004(2) 0.031(3) N1 0.038(3) 0.038(3) 0.033(3) 0.010(2) 0.006(2) 0.008(2) O3 0.090(4) 0.099(5) 0.062(4) -0.009(3) 0.017(3) 0.042(4) C12 0.118(8) 0.107(8) 0.021(4) 0.003(4) 0.001(5) 0.047(7) C11 0.106(7) 0.067(6) 0.048(5) 0.018(4) 0.017(5) 0.020(5) C10 0.060(5) 0.054(4) 0.031(4) 0.011(3) 0.011(3) 0.004(4) C9 0.027(3) 0.034(3) 0.034(3) 0.000(3) 0.002(3) 0.008(3) C8 0.025(3) 0.026(3) 0.032(3) -0.002(3) 0.006(2) 0.003(3) C7 0.029(3) 0.036(3) 0.031(3) 0.006(3) 0.009(3) 0.012(3) C21 0.030(3) 0.018(3) 0.036(3) 0.004(2) 0.009(3) -0.002(3) C26 0.040(4) 0.027(3) 0.038(3) 0.005(3) 0.006(3) 0.014(3) C25 0.029(3) 0.031(3) 0.032(3) 0.004(3) 0.008(3) 0.001(3) C27 0.044(4) 0.036(4) 0.043(4) 0.012(3) 0.005(3) 0.014(3) C28 0.031(3) 0.032(3) 0.030(3) 0.005(3) 0.004(3) 0.003(3) C29 0.049(4) 0.057(4) 0.043(4) 0.012(3) -0.001(3) 0.015(4) C30 0.038(4) 0.067(5) 0.025(3) 0.007(3) 0.001(3) -0.006(4) C31 0.037(4) 0.045(4) 0.031(3) -0.012(3) 0.000(3) -0.007(3) N2 0.059(4) 0.057(4) 0.036(3) -0.010(3) 0.008(3) -0.004(3) C33 0.039(4) 0.047(4) 0.030(3) 0.003(3) -0.004(3) 0.009(3) C32 0.032(4) 0.051(4) 0.039(4) 0.003(3) 0.010(3) 0.012(3) C22 0.048(4) 0.033(4) 0.046(4) -0.002(3) 0.009(3) 0.016(3) C23 0.057(5) 0.041(4) 0.055(4) 0.004(3) -0.003(4) 0.031(4) C24 0.040(4) 0.034(4) 0.035(3) 0.004(3) -0.002(3) 0.008(3) C1 0.028(3) 0.033(3) 0.033(3) -0.002(3) 0.002(3) 0.011(3) C6 0.044(4) 0.041(4) 0.057(4) -0.006(3) 0.023(3) 0.003(3) C5 0.060(5) 0.039(4) 0.071(5) -0.011(4) 0.003(4) -0.003(4) C4 0.072(5) 0.042(4) 0.045(4) -0.016(3) -0.010(4) 0.008(4) C3 0.071(5) 0.053(5) 0.047(4) -0.016(4) 0.018(4) 0.010(4) C2 0.052(4) 0.036(4) 0.051(4) -0.007(3) 0.021(3) -0.003(3) C13 0.077(6) 0.095(7) 0.060(5) -0.007(5) -0.033(5) 0.033(5) C14 0.042(4) 0.067(5) 0.052(4) 0.000(4) -0.003(3) 0.005(4) C15 0.027(3) 0.022(3) 0.031(3) 0.008(2) 0.005(2) 0.008(3) C20 0.040(4) 0.028(3) 0.044(4) -0.005(3) -0.005(3) 0.012(3) C19 0.039(4) 0.059(5) 0.048(4) -0.010(4) -0.015(3) 0.003(4) C18 0.068(5) 0.056(5) 0.058(5) -0.027(4) 0.001(4) 0.007(4) C17 0.067(5) 0.022(4) 0.088(6) -0.007(4) 0.012(4) 0.011(4) C16 0.035(4) 0.024(3) 0.055(4) 0.000(3) 0.000(3) 0.011(3) 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 123.3(5) . . ? C13 C12 C11 119.6(7) . . ? C12 C11 C10 119.5(8) . . ? C11 C10 C9 121.7(7) . . ? C10 C9 C8 120.1(5) . . ? C14 C9 C10 118.1(6) . . ? C14 C9 C8 121.7(5) . . ? C9 C8 C15 114.5(5) . . ? C7 C8 C9 123.9(5) . . ? C7 C8 C15 121.6(5) . . ? C8 C7 C21 120.9(5) . . ? C8 C7 C1 125.4(5) . . ? C21 C7 C1 113.8(5) . . ? C26 C21 C7 123.7(5) . . ? C26 C21 C22 115.6(5) . . ? C22 C21 C7 120.7(5) . . ? C21 C26 C25 124.1(5) . . ? C26 C25 C27 120.3(5) . . ? C26 C25 C24 118.2(5) . . ? C24 C25 C27 121.5(5) . . ? N1 C27 C25 120.9(5) . . ? C29 C28 N1 115.6(5) . . ? C29 C28 C33 118.3(5) . . ? C33 C28 N1 126.1(5) . . ? C28 C29 C30 121.6(6) . . ? C31 C30 C29 116.7(6) . . ? C30 C31 N2 116.2(6) . . ? C32 C31 C30 123.4(6) . . ? C32 C31 N2 120.4(6) . . ? O2 N2 O3 122.9(6) . . ? O2 N2 C31 119.9(6) . . ? O3 N2 C31 117.3(6) . . ? C32 C33 C28 121.2(5) . . ? C31 C32 C33 118.7(6) . . ? C23 C22 C21 122.9(5) . . ? C22 C23 C24 120.0(5) . . ? O1 C24 C25 122.0(5) . . ? O1 C24 C23 118.8(5) . . ? C23 C24 C25 119.2(5) . . ? C6 C1 C7 121.0(5) . . ? C2 C1 C7 120.7(5) . . ? C2 C1 C6 118.2(6) . . ? C5 C6 C1 120.3(6) . . ? C4 C5 C6 120.7(7) . . ? C3 C4 C5 120.3(6) . . ? C4 C3 C2 120.3(6) . . ? C1 C2 C3 120.1(6) . . ? C12 C13 C14 121.2(8) . . ? C9 C14 C13 119.8(7) . . ? C20 C15 C8 120.9(5) . . ? C16 C15 C8 121.4(5) . . ? C16 C15 C20 117.7(5) . . ? C19 C20 C15 121.7(5) . . ? C20 C19 C18 119.2(6) . . ? C17 C18 C19 119.6(6) . . ? C16 C17 C18 120.6(6) . . ? C17 C16 C15 121.1(6) . . ? 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 O2 N2 1.197(6) . ? O1 C24 1.343(6) . ? N1 C27 1.277(7) . ? N1 C28 1.423(6) . ? O3 N2 1.224(7) . ? C12 C11 1.368(10) . ? C12 C13 1.359(11) . ? C11 C10 1.379(9) . ? C10 C9 1.380(7) . ? C9 C8 1.493(7) . ? C9 C14 1.376(8) . ? C8 C7 1.329(7) . ? C8 C15 1.498(7) . ? C7 C21 1.498(7) . ? C7 C1 1.501(7) . ? C21 C26 1.374(7) . ? C21 C22 1.389(7) . ? C26 C25 1.389(7) . ? C25 C27 1.442(7) . ? C25 C24 1.401(7) . ? C28 C29 1.378(7) . ? C28 C33 1.388(7) . ? C29 C30 1.387(8) . ? C30 C31 1.377(8) . ? C31 N2 1.484(7) . ? C31 C32 1.350(7) . ? C33 C32 1.363(7) . ? C22 C23 1.377(8) . ? C23 C24 1.383(8) . ? C1 C6 1.385(8) . ? C1 C2 1.378(7) . ? C6 C5 1.377(8) . ? C5 C4 1.356(8) . ? C4 C3 1.341(9) . ? C3 C2 1.401(8) . ? C13 C14 1.390(9) . ? C15 C20 1.392(7) . ? C15 C16 1.376(6) . ? C20 C19 1.366(8) . ? C19 C18 1.386(8) . ? C18 C17 1.370(9) . ? C17 C16 1.364(8) . ? 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 1.86 2.582(6) 146.8 . C29 H29 O1 0.93 2.54 3.385(7) 152.0 2_566 C32 H32 O3 0.93 2.47 3.319(8) 152.2 2_756