#------------------------------------------------------------------------------ #$Date: 2026-06-04 10:23:32 +0100 (Thu, 04 Jun 2026) $ #$Revision: 306202 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577355.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_1577355 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 H25 N O' _chemical_formula_sum 'C33 H25 N O' _chemical_formula_weight 451.54 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _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 90 _cell_angle_beta 92.524(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.5319(15) _cell_length_b 13.7924(19) _cell_length_c 17.028(2) _cell_measurement_reflns_used 1010 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.30 _cell_measurement_theta_min 2.55 _cell_volume 2471.1(6) _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 'ShelXD (Sheldrick, 2008)' _diffrn_ambient_temperature 173.0 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.987 _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 0.0775 _diffrn_reflns_av_unetI/netI 0.0888 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 25371 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.271 _diffrn_reflns_theta_min 2.813 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.214 _exptl_crystal_description block _exptl_crystal_F_000 952 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.205 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 316 _refine_ls_number_reflns 6039 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.140 _refine_ls_R_factor_all 0.1770 _refine_ls_R_factor_gt 0.1107 _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^)+(0.0466P)^2^+2.0302P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1824 _refine_ls_wR_factor_ref 0.2042 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3523 _reflns_number_total 6039 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc00735j2.cif _cod_data_source_block shelx _cod_database_code 1577355 _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 0.993 _shelx_estimated_absorpt_t_min 0.989 _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: C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33) 2.b Tetrahedral OH refined with riding coordinates: O1(H1A) ; _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL AA_a.res in P2(1)/n CELL 0.71073 10.5319 13.7924 17.0282 90 92.524 90 ZERR 4 0.0015 0.0019 0.0024 0 0.005 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 132 100 4 4 L.S. 4 PLAN 20 SIZE 0.13 0.1 0.16 TEMP -100.15 HTAB O1 N1 BOND $H CONF fmap 2 acta MERG 2 REM REM REM WGHT 0.046600 2.030200 FVAR 1.12480 C1 1 0.522876 0.076232 0.246442 11.00000 0.06097 0.04198 = 0.06346 0.01253 0.01635 -0.00250 AFIX 43 H1 2 0.598966 0.089627 0.276520 11.00000 -1.20000 AFIX 0 N1 3 0.579964 0.543580 0.306238 11.00000 0.06185 0.03981 = 0.06526 0.00490 -0.00652 -0.01291 C2 1 0.529208 0.041499 0.170151 11.00000 0.09791 0.04770 = 0.07853 0.01323 0.04775 0.00634 AFIX 43 H2 2 0.609568 0.029801 0.148735 11.00000 -1.20000 AFIX 0 O1 4 0.664946 0.471838 0.442029 11.00000 0.10597 0.06398 = 0.08023 0.00652 -0.03445 -0.03891 AFIX 83 H1A 2 0.654857 0.513734 0.406498 11.00000 -1.50000 AFIX 0 C3 1 0.420170 0.024057 0.125702 11.00000 0.14372 0.04977 = 0.04835 0.00423 0.02369 -0.00814 AFIX 43 H3 2 0.424776 0.000480 0.073485 11.00000 -1.20000 AFIX 0 C4 1 0.305333 0.040566 0.156489 11.00000 0.10887 0.05840 = 0.04322 0.00829 -0.00879 -0.01133 AFIX 43 H4 2 0.229713 0.029079 0.125400 11.00000 -1.20000 AFIX 0 C5 1 0.297655 0.073623 0.231949 11.00000 0.05808 0.04423 = 0.04622 0.01226 -0.00357 -0.00266 AFIX 43 H5 2 0.216501 0.084558 0.252532 11.00000 -1.20000 AFIX 0 C6 1 0.406137 0.091460 0.278941 11.00000 0.05098 0.02763 = 0.04233 0.01168 0.00565 -0.00246 C7 1 0.397306 0.128574 0.360822 11.00000 0.03889 0.03325 = 0.04446 0.00692 -0.00312 -0.00091 C8 1 0.322154 0.087616 0.413678 11.00000 0.03863 0.03525 = 0.03988 0.00166 -0.00137 -0.00225 C9 1 0.256949 -0.008041 0.401992 11.00000 0.04083 0.03406 = 0.02785 0.00181 0.00143 -0.00340 C10 1 0.316951 -0.087952 0.371928 11.00000 0.04264 0.04005 = 0.04352 0.00432 0.00476 0.00226 AFIX 43 H10 2 0.402502 -0.082818 0.356914 11.00000 -1.20000 AFIX 0 C11 1 0.253816 -0.175222 0.363483 11.00000 0.06361 0.03427 = 0.04881 0.00010 0.00256 0.00366 AFIX 43 H11 2 0.296270 -0.229238 0.342052 11.00000 -1.20000 AFIX 0 C12 1 0.131369 -0.185293 0.385395 11.00000 0.06676 0.04562 = 0.04402 -0.00415 -0.00168 -0.01663 AFIX 43 H12 2 0.088714 -0.245727 0.379570 11.00000 -1.20000 AFIX 0 C13 1 0.071413 -0.107144 0.415768 11.00000 0.04741 0.06727 = 0.05296 -0.01255 0.01105 -0.02064 AFIX 43 H13 2 -0.013665 -0.113328 0.431447 11.00000 -1.20000 AFIX 0 C14 1 0.133072 -0.018811 0.424042 11.00000 0.04574 0.04441 = 0.04599 -0.01314 0.00794 -0.00619 AFIX 43 H14 2 0.089691 0.034984 0.445119 11.00000 -1.20000 AFIX 0 C15 1 0.292637 0.137796 0.488529 11.00000 0.03834 0.03764 = 0.05242 -0.00921 0.00264 -0.00894 C16 1 0.237581 0.228822 0.486639 11.00000 0.05600 0.04874 = 0.06963 -0.01168 0.00589 -0.00485 AFIX 43 H16 2 0.222063 0.260636 0.437672 11.00000 -1.20000 AFIX 0 C17 1 0.205033 0.273784 0.555130 11.00000 0.06208 0.05850 = 0.10015 -0.03018 0.00405 -0.00123 AFIX 43 H17 2 0.166294 0.335983 0.552864 11.00000 -1.20000 AFIX 0 C18 1 0.227706 0.230192 0.625807 11.00000 0.06599 0.08800 = 0.07999 -0.04665 0.01165 -0.02019 AFIX 43 H18 2 0.205719 0.261966 0.672807 11.00000 -1.20000 AFIX 0 C19 1 0.282671 0.139789 0.629007 11.00000 0.07790 0.08023 = 0.04947 -0.01604 -0.00007 -0.02601 AFIX 43 H19 2 0.299467 0.109270 0.678390 11.00000 -1.20000 AFIX 0 C20 1 0.313568 0.093173 0.560562 11.00000 0.05939 0.05169 = 0.05167 -0.00709 -0.00021 -0.01285 AFIX 43 H20 2 0.349453 0.029997 0.563085 11.00000 -1.20000 AFIX 0 C21 1 0.544730 0.227311 0.450990 11.00000 0.05395 0.05266 = 0.05453 0.01713 -0.01024 -0.01184 AFIX 43 H21 2 0.549360 0.174339 0.486660 11.00000 -1.20000 AFIX 0 C22 1 0.608365 0.311150 0.469910 11.00000 0.06596 0.06624 = 0.05169 0.01432 -0.02058 -0.02029 AFIX 43 H22 2 0.656338 0.315351 0.518357 11.00000 -1.20000 AFIX 0 C23 1 0.603950 0.389503 0.419831 11.00000 0.05713 0.04933 = 0.05808 0.00061 -0.01002 -0.01933 C24 1 0.537329 0.382039 0.346924 11.00000 0.04819 0.03693 = 0.05189 0.00342 -0.00520 -0.00593 C25 1 0.473717 0.295384 0.329393 11.00000 0.04869 0.04165 = 0.04504 0.00203 -0.00552 -0.00780 AFIX 43 H25 2 0.428790 0.289641 0.280001 11.00000 -1.20000 AFIX 0 C26 1 0.473007 0.217819 0.380318 11.00000 0.04076 0.03974 = 0.04537 0.00752 0.00030 -0.00338 C27 1 0.532631 0.460495 0.291503 11.00000 0.05458 0.03991 = 0.05504 0.00197 -0.00581 -0.00633 AFIX 43 H27 2 0.492110 0.449757 0.241308 11.00000 -1.20000 AFIX 0 C28 1 0.575269 0.615696 0.246691 11.00000 0.04806 0.03616 = 0.06024 0.00338 -0.00561 -0.01162 C29 1 0.525240 0.704450 0.263969 11.00000 0.07395 0.04490 = 0.07780 0.00396 0.00728 -0.00237 AFIX 43 H29 2 0.493764 0.716057 0.314550 11.00000 -1.20000 AFIX 0 C30 1 0.520429 0.776595 0.208525 11.00000 0.09959 0.04813 = 0.09891 0.00945 -0.00464 0.00442 AFIX 43 H30 2 0.481741 0.836894 0.219946 11.00000 -1.20000 AFIX 0 C31 1 0.570443 0.762349 0.137722 11.00000 0.11473 0.05550 = 0.08756 0.02249 -0.01471 -0.02172 AFIX 43 H31 2 0.568871 0.813153 0.100020 11.00000 -1.20000 AFIX 0 C32 1 0.623069 0.675240 0.120404 11.00000 0.10513 0.08021 = 0.06067 0.00817 0.01105 -0.02761 AFIX 43 H32 2 0.659007 0.665342 0.070835 11.00000 -1.20000 AFIX 0 C33 1 0.624081 0.601489 0.174932 11.00000 0.08059 0.05050 = 0.07255 -0.00117 0.00779 -0.00169 AFIX 43 H33 2 0.659115 0.540245 0.162355 11.00000 -1.20000 AFIX 0 HKLF 4 REM AA_a.res in P2(1)/n REM R1 = 0.1107 for 3523 Fo > 4sig(Fo) and 0.1770 for all 6039 data REM 316 parameters refined using 0 restraints END WGHT 0.0435 1.7247 REM Highest difference peak 0.205, deepest hole -0.238, 1-sigma level 0.039 Q1 1 0.3877 0.1144 0.3171 11.00000 0.05 0.21 Q2 1 0.2434 -0.0144 0.4473 11.00000 0.05 0.20 Q3 1 0.2775 -0.0265 0.3587 11.00000 0.05 0.19 Q4 1 0.3159 0.1223 0.3700 11.00000 0.05 0.18 Q5 1 0.1547 -0.0030 0.3738 11.00000 0.05 0.17 Q6 1 0.3343 0.1021 0.4603 11.00000 0.05 0.17 Q7 1 0.5262 0.4022 0.3933 11.00000 0.05 0.17 Q8 1 0.3186 0.0209 0.2075 11.00000 0.05 0.17 Q9 1 0.4764 0.7193 0.1985 11.00000 0.05 0.16 Q10 1 0.0751 -0.1185 0.3692 11.00000 0.05 0.16 Q11 1 0.4841 0.2246 0.3309 11.00000 0.05 0.16 Q12 1 0.5285 0.0953 0.1950 11.00000 0.05 0.16 Q13 1 0.2803 -0.1367 0.4035 11.00000 0.05 0.16 Q14 1 0.3510 -0.0767 0.3320 11.00000 0.05 0.16 Q15 1 0.5397 0.3357 0.3313 11.00000 0.05 0.16 Q16 1 0.5952 0.3844 0.3685 11.00000 0.05 0.15 Q17 1 0.4098 0.0800 0.3856 11.00000 0.05 0.15 Q18 1 0.3079 0.0340 0.4175 11.00000 0.05 0.15 Q19 1 0.2524 0.1024 0.5214 11.00000 0.05 0.15 Q20 1 0.4805 0.2854 0.2780 11.00000 0.05 0.15 ; _shelx_res_checksum 71489 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 C1 C 0.5229(3) 0.0762(2) 0.2464(2) 0.0551(9) Uani 1 1 d . . . . . H1 H 0.5990 0.0896 0.2765 0.066 Uiso 1 1 calc R . . . . N1 N 0.5800(3) 0.54358(19) 0.30624(17) 0.0559(8) Uani 1 1 d . . . . . C2 C 0.5292(5) 0.0415(3) 0.1702(3) 0.0734(12) Uani 1 1 d . . . . . H2 H 0.6096 0.0298 0.1487 0.088 Uiso 1 1 calc R . . . . O1 O 0.6649(3) 0.47184(19) 0.44203(16) 0.0845(9) Uani 1 1 d . . . . . H1A H 0.6549 0.5137 0.4065 0.127 Uiso 1 1 calc R . . . . C3 C 0.4202(6) 0.0241(3) 0.1257(2) 0.0800(14) Uani 1 1 d . . . . . H3 H 0.4248 0.0005 0.0735 0.096 Uiso 1 1 calc R . . . . C4 C 0.3053(5) 0.0406(3) 0.1565(2) 0.0705(11) Uani 1 1 d . . . . . H4 H 0.2297 0.0291 0.1254 0.085 Uiso 1 1 calc R . . . . C5 C 0.2977(3) 0.0736(2) 0.23195(18) 0.0497(8) Uani 1 1 d . . . . . H5 H 0.2165 0.0846 0.2525 0.060 Uiso 1 1 calc R . . . . C6 C 0.4061(3) 0.0915(2) 0.27894(17) 0.0402(7) Uani 1 1 d . . . . . C7 C 0.3973(3) 0.1286(2) 0.36082(17) 0.0390(7) Uani 1 1 d . . . . . C8 C 0.3222(3) 0.0876(2) 0.41368(17) 0.0380(7) Uani 1 1 d . . . . . C9 C 0.2569(3) -0.0080(2) 0.40199(15) 0.0342(6) Uani 1 1 d . . . . . C10 C 0.3170(3) -0.0880(2) 0.37193(17) 0.0420(7) Uani 1 1 d . . . . . H10 H 0.4025 -0.0828 0.3569 0.050 Uiso 1 1 calc R . . . . C11 C 0.2538(3) -0.1752(2) 0.36348(19) 0.0489(8) Uani 1 1 d . . . . . H11 H 0.2963 -0.2292 0.3421 0.059 Uiso 1 1 calc R . . . . C12 C 0.1314(3) -0.1853(2) 0.38540(18) 0.0523(9) Uani 1 1 d . . . . . H12 H 0.0887 -0.2457 0.3796 0.063 Uiso 1 1 calc R . . . . C13 C 0.0714(3) -0.1071(3) 0.41577(19) 0.0556(9) Uani 1 1 d . . . . . H13 H -0.0137 -0.1133 0.4314 0.067 Uiso 1 1 calc R . . . . C14 C 0.1331(3) -0.0188(2) 0.42404(18) 0.0452(8) Uani 1 1 d . . . . . H14 H 0.0897 0.0350 0.4451 0.054 Uiso 1 1 calc R . . . . C15 C 0.2926(3) 0.1378(2) 0.48853(18) 0.0428(7) Uani 1 1 d . . . . . C16 C 0.2376(3) 0.2288(3) 0.4866(2) 0.0580(9) Uani 1 1 d . . . . . H16 H 0.2221 0.2606 0.4377 0.070 Uiso 1 1 calc R . . . . C17 C 0.2050(4) 0.2738(3) 0.5551(3) 0.0736(12) Uani 1 1 d . . . . . H17 H 0.1663 0.3360 0.5529 0.088 Uiso 1 1 calc R . . . . C18 C 0.2277(4) 0.2302(4) 0.6258(3) 0.0777(13) Uani 1 1 d . . . . . H18 H 0.2057 0.2620 0.6728 0.093 Uiso 1 1 calc R . . . . C19 C 0.2827(4) 0.1398(3) 0.6290(2) 0.0693(11) Uani 1 1 d . . . . . H19 H 0.2995 0.1093 0.6784 0.083 Uiso 1 1 calc R . . . . C20 C 0.3136(3) 0.0932(3) 0.5606(2) 0.0543(9) Uani 1 1 d . . . . . H20 H 0.3495 0.0300 0.5631 0.065 Uiso 1 1 calc R . . . . C21 C 0.5447(3) 0.2273(3) 0.4510(2) 0.0541(9) Uani 1 1 d . . . . . H21 H 0.5494 0.1743 0.4867 0.065 Uiso 1 1 calc R . . . . C22 C 0.6084(3) 0.3112(3) 0.4699(2) 0.0620(10) Uani 1 1 d . . . . . H22 H 0.6563 0.3154 0.5184 0.074 Uiso 1 1 calc R . . . . C23 C 0.6040(3) 0.3895(2) 0.4198(2) 0.0552(9) Uani 1 1 d . . . . . C24 C 0.5373(3) 0.3820(2) 0.34692(19) 0.0459(8) Uani 1 1 d . . . . . C25 C 0.4737(3) 0.2954(2) 0.32939(18) 0.0453(8) Uani 1 1 d . . . . . H25 H 0.4288 0.2896 0.2800 0.054 Uiso 1 1 calc R . . . . C26 C 0.4730(3) 0.2178(2) 0.38032(18) 0.0420(7) Uani 1 1 d . . . . . C27 C 0.5326(3) 0.4605(2) 0.2915(2) 0.0501(8) Uani 1 1 d . . . . . H27 H 0.4921 0.4498 0.2413 0.060 Uiso 1 1 calc R . . . . C28 C 0.5753(3) 0.6157(2) 0.2467(2) 0.0484(8) Uani 1 1 d . . . . . C29 C 0.5252(4) 0.7044(3) 0.2640(2) 0.0654(10) Uani 1 1 d . . . . . H29 H 0.4938 0.7161 0.3145 0.079 Uiso 1 1 calc R . . . . C30 C 0.5204(5) 0.7766(3) 0.2085(3) 0.0825(13) Uani 1 1 d . . . . . H30 H 0.4817 0.8369 0.2199 0.099 Uiso 1 1 calc R . . . . C31 C 0.5704(5) 0.7623(3) 0.1377(3) 0.0865(14) Uani 1 1 d . . . . . H31 H 0.5689 0.8132 0.1000 0.104 Uiso 1 1 calc R . . . . C32 C 0.6231(4) 0.6752(3) 0.1204(2) 0.0818(13) Uani 1 1 d . . . . . H32 H 0.6590 0.6653 0.0708 0.098 Uiso 1 1 calc R . . . . C33 C 0.6241(4) 0.6015(3) 0.1749(2) 0.0677(11) Uani 1 1 d . . . . . H33 H 0.6591 0.5402 0.1624 0.081 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 C1 0.061(2) 0.0420(19) 0.063(2) 0.0125(17) 0.0163(18) -0.0025(16) N1 0.0618(19) 0.0398(16) 0.0653(19) 0.0049(14) -0.0065(14) -0.0129(14) C2 0.098(3) 0.048(2) 0.079(3) 0.013(2) 0.048(3) 0.006(2) O1 0.106(2) 0.0640(17) 0.0802(19) 0.0065(14) -0.0344(16) -0.0389(16) C3 0.144(5) 0.050(2) 0.048(2) 0.0042(19) 0.024(3) -0.008(3) C4 0.109(4) 0.058(2) 0.043(2) 0.0083(18) -0.009(2) -0.011(2) C5 0.058(2) 0.0442(19) 0.0462(19) 0.0123(15) -0.0036(16) -0.0027(16) C6 0.0510(19) 0.0276(15) 0.0423(17) 0.0117(13) 0.0057(14) -0.0025(14) C7 0.0389(17) 0.0332(16) 0.0445(17) 0.0069(13) -0.0031(13) -0.0009(13) C8 0.0386(16) 0.0352(16) 0.0399(16) 0.0017(13) -0.0014(13) -0.0023(13) C9 0.0408(17) 0.0341(15) 0.0278(14) 0.0018(12) 0.0014(12) -0.0034(13) C10 0.0426(17) 0.0400(17) 0.0435(17) 0.0043(14) 0.0048(13) 0.0023(14) C11 0.064(2) 0.0343(17) 0.0488(19) 0.0001(15) 0.0026(16) 0.0037(16) C12 0.067(2) 0.046(2) 0.0440(18) -0.0042(16) -0.0017(16) -0.0166(17) C13 0.047(2) 0.067(2) 0.053(2) -0.0126(18) 0.0111(16) -0.0206(18) C14 0.0457(19) 0.0444(18) 0.0460(18) -0.0131(15) 0.0079(14) -0.0062(15) C15 0.0383(17) 0.0376(17) 0.0524(19) -0.0092(15) 0.0026(14) -0.0089(14) C16 0.056(2) 0.049(2) 0.070(2) -0.0117(19) 0.0059(18) -0.0048(17) C17 0.062(3) 0.059(2) 0.100(3) -0.030(3) 0.004(2) -0.001(2) C18 0.066(3) 0.088(3) 0.080(3) -0.047(3) 0.012(2) -0.020(2) C19 0.078(3) 0.080(3) 0.049(2) -0.016(2) -0.0001(19) -0.026(2) C20 0.059(2) 0.052(2) 0.052(2) -0.0071(17) -0.0002(16) -0.0128(17) C21 0.054(2) 0.053(2) 0.055(2) 0.0171(17) -0.0102(16) -0.0118(17) C22 0.066(2) 0.066(2) 0.052(2) 0.0143(18) -0.0206(17) -0.020(2) C23 0.057(2) 0.049(2) 0.058(2) 0.0006(17) -0.0100(17) -0.0193(17) C24 0.0482(19) 0.0369(17) 0.0519(19) 0.0034(15) -0.0052(15) -0.0059(14) C25 0.0487(19) 0.0416(18) 0.0450(18) 0.0020(14) -0.0055(14) -0.0078(15) C26 0.0408(18) 0.0397(17) 0.0454(17) 0.0075(14) 0.0003(14) -0.0034(14) C27 0.055(2) 0.0399(18) 0.055(2) 0.0020(16) -0.0058(16) -0.0063(16) C28 0.0481(19) 0.0362(18) 0.060(2) 0.0034(16) -0.0056(16) -0.0116(15) C29 0.074(3) 0.045(2) 0.078(3) 0.0040(19) 0.007(2) -0.0024(19) C30 0.100(4) 0.048(2) 0.099(4) 0.009(2) -0.005(3) 0.004(2) C31 0.115(4) 0.055(3) 0.088(3) 0.022(3) -0.015(3) -0.022(3) C32 0.105(4) 0.080(3) 0.061(3) 0.008(2) 0.011(2) -0.028(3) C33 0.081(3) 0.051(2) 0.073(3) -0.001(2) 0.008(2) -0.002(2) 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 C2 C1 H1 119.8 . . ? C6 C1 H1 119.8 . . ? C6 C1 C2 120.4(4) . . ? C27 N1 C28 119.3(3) . . ? C1 C2 H2 119.9 . . ? C3 C2 C1 120.3(4) . . ? C3 C2 H2 119.9 . . ? C23 O1 H1A 109.5 . . ? C2 C3 H3 120.1 . . ? C4 C3 C2 119.8(4) . . ? C4 C3 H3 120.1 . . ? C3 C4 H4 119.7 . . ? C3 C4 C5 120.6(4) . . ? C5 C4 H4 119.7 . . ? C4 C5 H5 119.4 . . ? C4 C5 C6 121.3(4) . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 117.7(3) . . ? C1 C6 C7 121.2(3) . . ? C5 C6 C7 121.1(3) . . ? C6 C7 C26 115.8(3) . . ? C8 C7 C6 122.9(3) . . ? C8 C7 C26 121.3(3) . . ? C7 C8 C9 124.1(3) . . ? C7 C8 C15 121.7(3) . . ? C15 C8 C9 114.2(2) . . ? C10 C9 C8 122.6(3) . . ? C10 C9 C14 117.9(3) . . ? C14 C9 C8 119.5(3) . . ? C9 C10 H10 119.7 . . ? C11 C10 C9 120.6(3) . . ? C11 C10 H10 119.7 . . ? C10 C11 H11 119.4 . . ? C12 C11 C10 121.1(3) . . ? C12 C11 H11 119.4 . . ? C11 C12 H12 120.6 . . ? C13 C12 C11 118.8(3) . . ? C13 C12 H12 120.6 . . ? C12 C13 H13 119.6 . . ? C12 C13 C14 120.8(3) . . ? C14 C13 H13 119.6 . . ? C9 C14 C13 120.7(3) . . ? C9 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C16 C15 C8 120.2(3) . . ? C20 C15 C8 121.3(3) . . ? C20 C15 C16 118.4(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 C15 120.6(4) . . ? C17 C16 H16 119.7 . . ? C16 C17 H17 119.6 . . ? C18 C17 C16 120.7(4) . . ? C18 C17 H17 119.6 . . ? C17 C18 H18 120.2 . . ? C17 C18 C19 119.6(4) . . ? C19 C18 H18 120.2 . . ? C18 C19 H19 119.9 . . ? C18 C19 C20 120.2(4) . . ? C20 C19 H19 119.9 . . ? C15 C20 C19 120.5(4) . . ? C15 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C22 C21 H21 119.3 . . ? C22 C21 C26 121.5(3) . . ? C26 C21 H21 119.3 . . ? C21 C22 H22 119.5 . . ? C21 C22 C23 121.0(3) . . ? C23 C22 H22 119.5 . . ? O1 C23 C22 119.0(3) . . ? O1 C23 C24 121.5(3) . . ? C22 C23 C24 119.5(3) . . ? C23 C24 C27 121.9(3) . . ? C25 C24 C23 118.0(3) . . ? C25 C24 C27 120.2(3) . . ? C24 C25 H25 118.4 . . ? C26 C25 C24 123.1(3) . . ? C26 C25 H25 118.4 . . ? C21 C26 C7 122.0(3) . . ? C25 C26 C7 121.1(3) . . ? C25 C26 C21 116.8(3) . . ? N1 C27 C24 123.3(3) . . ? N1 C27 H27 118.4 . . ? C24 C27 H27 118.4 . . ? C29 C28 N1 118.3(3) . . ? C33 C28 N1 122.5(3) . . ? C33 C28 C29 119.1(3) . . ? C28 C29 H29 119.9 . . ? C28 C29 C30 120.2(4) . . ? C30 C29 H29 119.9 . . ? C29 C30 H30 119.8 . . ? C31 C30 C29 120.3(4) . . ? C31 C30 H30 119.8 . . ? C30 C31 H31 120.0 . . ? C30 C31 C32 120.0(4) . . ? C32 C31 H31 120.0 . . ? C31 C32 H32 120.1 . . ? C31 C32 C33 119.8(4) . . ? C33 C32 H32 120.1 . . ? C28 C33 C32 120.5(4) . . ? C28 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? 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 C1 H1 0.9500 . ? C1 C2 1.389(5) . ? C1 C6 1.386(4) . ? N1 C27 1.270(4) . ? N1 C28 1.420(4) . ? C2 H2 0.9500 . ? C2 C3 1.369(6) . ? O1 H1A 0.8400 . ? O1 C23 1.350(4) . ? C3 H3 0.9500 . ? C3 C4 1.358(6) . ? C4 H4 0.9500 . ? C4 C5 1.369(5) . ? C5 H5 0.9500 . ? C5 C6 1.388(4) . ? C6 C7 1.492(4) . ? C7 C8 1.348(4) . ? C7 C26 1.496(4) . ? C8 C9 1.497(4) . ? C8 C15 1.495(4) . ? C9 C10 1.380(4) . ? C9 C14 1.381(4) . ? C10 H10 0.9500 . ? C10 C11 1.380(4) . ? C11 H11 0.9500 . ? C11 C12 1.365(5) . ? C12 H12 0.9500 . ? C12 C13 1.363(5) . ? C13 H13 0.9500 . ? C13 C14 1.385(4) . ? C14 H14 0.9500 . ? C15 C16 1.383(5) . ? C15 C20 1.381(4) . ? C16 H16 0.9500 . ? C16 C17 1.377(5) . ? C17 H17 0.9500 . ? C17 C18 1.357(6) . ? C18 H18 0.9500 . ? C18 C19 1.375(6) . ? C19 H19 0.9500 . ? C19 C20 1.382(5) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C21 C22 1.368(5) . ? C21 C26 1.399(4) . ? C22 H22 0.9500 . ? C22 C23 1.376(5) . ? C23 C24 1.403(4) . ? C24 C25 1.396(4) . ? C24 C27 1.435(4) . ? C25 H25 0.9500 . ? C25 C26 1.377(4) . ? C27 H27 0.9500 . ? C28 C29 1.370(5) . ? C28 C33 1.361(5) . ? C29 H29 0.9500 . ? C29 C30 1.371(5) . ? C30 H30 0.9500 . ? C30 C31 1.351(6) . ? C31 H31 0.9500 . ? C31 C32 1.361(6) . ? C32 H32 0.9500 . ? C32 C33 1.377(5) . ? C33 H33 0.9500 . ? 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 H1A N1 0.84 1.89 2.635(4) 146.4 . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 C4 -0.2(6) . . . . ? C1 C6 C7 C8 -131.8(3) . . . . ? C1 C6 C7 C26 50.9(4) . . . . ? N1 C28 C29 C30 179.1(3) . . . . ? N1 C28 C33 C32 -176.7(3) . . . . ? C2 C1 C6 C5 -1.9(4) . . . . ? C2 C1 C6 C7 179.9(3) . . . . ? C2 C3 C4 C5 -0.7(6) . . . . ? O1 C23 C24 C25 -178.2(3) . . . . ? O1 C23 C24 C27 1.3(5) . . . . ? C3 C4 C5 C6 0.2(5) . . . . ? C4 C5 C6 C1 1.1(5) . . . . ? C4 C5 C6 C7 179.3(3) . . . . ? C5 C6 C7 C8 50.1(4) . . . . ? C5 C6 C7 C26 -127.2(3) . . . . ? C6 C1 C2 C3 1.5(5) . . . . ? C6 C7 C8 C9 10.9(4) . . . . ? C6 C7 C8 C15 -166.3(3) . . . . ? C6 C7 C26 C21 -136.3(3) . . . . ? C6 C7 C26 C25 44.6(4) . . . . ? C7 C8 C9 C10 43.5(4) . . . . ? C7 C8 C9 C14 -138.5(3) . . . . ? C7 C8 C15 C16 56.8(4) . . . . ? C7 C8 C15 C20 -126.4(3) . . . . ? C8 C7 C26 C21 46.4(4) . . . . ? C8 C7 C26 C25 -132.8(3) . . . . ? C8 C9 C10 C11 178.8(3) . . . . ? C8 C9 C14 C13 -178.4(3) . . . . ? C8 C15 C16 C17 177.2(3) . . . . ? C8 C15 C20 C19 -178.4(3) . . . . ? C9 C8 C15 C16 -120.6(3) . . . . ? C9 C8 C15 C20 56.2(4) . . . . ? C9 C10 C11 C12 -0.8(5) . . . . ? C10 C9 C14 C13 -0.3(5) . . . . ? C10 C11 C12 C13 0.3(5) . . . . ? C11 C12 C13 C14 0.3(5) . . . . ? C12 C13 C14 C9 -0.3(5) . . . . ? C14 C9 C10 C11 0.8(4) . . . . ? C15 C8 C9 C10 -139.1(3) . . . . ? C15 C8 C9 C14 38.9(4) . . . . ? C15 C16 C17 C18 0.8(6) . . . . ? C16 C15 C20 C19 -1.5(5) . . . . ? C16 C17 C18 C19 -0.6(6) . . . . ? C17 C18 C19 C20 -0.6(6) . . . . ? C18 C19 C20 C15 1.7(5) . . . . ? C20 C15 C16 C17 0.3(5) . . . . ? C21 C22 C23 O1 177.9(4) . . . . ? C21 C22 C23 C24 -2.5(6) . . . . ? C22 C21 C26 C7 -176.6(3) . . . . ? C22 C21 C26 C25 2.5(5) . . . . ? C22 C23 C24 C25 2.3(5) . . . . ? C22 C23 C24 C27 -178.2(3) . . . . ? C23 C24 C25 C26 0.4(5) . . . . ? C23 C24 C27 N1 -5.1(5) . . . . ? C24 C25 C26 C7 176.4(3) . . . . ? C24 C25 C26 C21 -2.7(5) . . . . ? C25 C24 C27 N1 174.4(3) . . . . ? C26 C7 C8 C9 -172.0(3) . . . . ? C26 C7 C8 C15 10.9(4) . . . . ? C26 C21 C22 C23 0.0(6) . . . . ? C27 N1 C28 C29 127.3(4) . . . . ? C27 N1 C28 C33 -56.1(5) . . . . ? C27 C24 C25 C26 -179.1(3) . . . . ? C28 N1 C27 C24 177.5(3) . . . . ? C28 C29 C30 C31 -3.2(7) . . . . ? C29 C28 C33 C32 -0.1(6) . . . . ? C29 C30 C31 C32 1.7(7) . . . . ? C30 C31 C32 C33 0.6(7) . . . . ? C31 C32 C33 C28 -1.4(6) . . . . ? C33 C28 C29 C30 2.4(6) . . . . ?