#------------------------------------------------------------------------------ #$Date: 2026-06-04 10:23:32 +0100 (Thu, 04 Jun 2026) $ #$Revision: 306202 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577361.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_1577361 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 'C34 H27 N O2, 2(H2 O)' _chemical_formula_sum 'C34 H31 N O4' _chemical_formula_weight 517.60 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _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 90.364(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 45.626(2) _cell_length_b 8.3057(4) _cell_length_c 16.4192(8) _cell_measurement_reflns_used 6449 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 26.86 _cell_measurement_theta_min 2.64 _cell_volume 6222.0(5) _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 0.810 _diffrn_measured_fraction_theta_max 0.810 _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 0.0643 _diffrn_reflns_av_unetI/netI 0.1074 _diffrn_reflns_Laue_measured_fraction_full 0.810 _diffrn_reflns_Laue_measured_fraction_max 0.810 _diffrn_reflns_limit_h_max 46 _diffrn_reflns_limit_h_min -54 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 14617 _diffrn_reflns_point_group_measured_fraction_full 0.810 _diffrn_reflns_point_group_measured_fraction_max 0.810 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 25.000 _diffrn_reflns_theta_min 2.642 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.105 _exptl_crystal_description block _exptl_crystal_F_000 2192 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _refine_diff_density_max 1.078 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.113 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.315 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 353 _refine_ls_number_reflns 4431 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.315 _refine_ls_R_factor_all 0.2024 _refine_ls_R_factor_gt 0.1541 _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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3765 _refine_ls_wR_factor_ref 0.4009 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2647 _reflns_number_total 4431 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc00735j2.cif _cod_data_source_block aaaa _cod_database_code 1577361 _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 0.991 _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 C(H,H,H) groups, All O(H) groups, All O(H,H) groups 2.a Riding coordinates: O1(H1), C10(H10), O4(H4A,H4B), O3(H3A,H3B) 2.b Aromatic/amide H refined with riding coordinates: C32(H32), C33(H33), C26(H26), C27(H27), C23(H23), C29(H29), C2(H2), C30(H30), C22(H22), C14(H14), C13(H13), C12(H12), C3(H3), C4(H4), C5(H5), C6(H6), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C11(H11) 2.c Idealised Me refined as rotating group: C34(H34A,H34B,H34C) ; _shelx_res_file ; aaaa.res created by SHELXL-2014/7 TITL AAAA_a.res in P-1 New: C2/c CELL 0.71073 45.626 8.3057 16.4192 90 90.364 90 ZERR 8 0.002 0.0004 0.0008 0 0.002 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C 2.310 20.844 1.02 10.208 1.589 0.569 0.865 51.651 0.216 0.003 0.002 = 11.5 0.68 12.01 SFAC H 0.493 10.511 0.323 26.126 0.14 3.142 0.041 57.8 0.003 0 0 0.624 = 0.35 1.008 SFAC N 12.213 0.006 3.132 9.893 2.013 28.998 1.166 0.583 -11.529 0.006 = 0.003 19.6 0.68 14.01 SFAC O 3.049 13.277 2.287 5.701 1.546 0.324 0.867 32.909 0.251 0.011 0.006 = 32.5 0.68 16 UNIT 272 248 8 32 EQIV $1 -X,+Y,0.5-Z L.S. 5 PLAN 20 SIZE 0.13 0.15 0.16 TEMP 0 HTAB O1 N1 HTAB O4 O3 HTAB O3 O4 HTAB O4 O3_$1 HTAB O3 O4_$1 fmap 2 acta OMIT 0 50 REM REM REM WGHT 0.200000 FVAR 0.44672 O1 4 0.177538 0.652089 0.054510 11.00000 0.07985 0.08323 = 0.07186 -0.03896 0.02330 0.00817 AFIX 3 H1 2 0.193058 0.701609 0.052420 11.00000 -1.50000 AFIX 0 O2 4 0.338558 0.808961 0.210539 11.00000 0.05880 0.07539 = 0.09271 0.00457 0.00696 0.01018 N1 3 0.218492 0.789140 0.142356 11.00000 0.04677 0.05831 = 0.06486 -0.00882 0.01166 0.00926 C10 1 0.058654 1.046309 0.432631 11.00000 0.05724 0.05036 = 0.03817 0.00608 0.00095 0.00596 AFIX 3 H10 2 0.057994 0.939589 0.439531 11.00000 -1.20000 AFIX 0 C34 1 0.349137 0.895858 0.277250 11.00000 0.05776 0.12271 = 0.09489 -0.01357 -0.01310 0.01174 AFIX 137 H34A 2 0.343175 0.843989 0.326699 11.00000 -1.50000 H34B 2 0.341367 1.003233 0.275660 11.00000 -1.50000 H34C 2 0.370147 0.900139 0.275289 11.00000 -1.50000 AFIX 0 C32 1 0.288715 0.898191 0.242899 11.00000 0.06803 0.13974 = 0.15027 -0.07945 0.00208 0.01813 AFIX 43 H32 2 0.295163 0.958090 0.287387 11.00000 -1.20000 AFIX 0 C31 1 0.308927 0.813905 0.197990 11.00000 0.05156 0.05525 = 0.07428 0.00644 0.01054 0.01597 C33 1 0.259948 0.896839 0.224605 11.00000 0.05934 0.15629 = 0.14307 -0.08367 0.01971 0.00356 AFIX 43 H33 2 0.247294 0.960744 0.254826 11.00000 -1.20000 AFIX 0 C26 1 0.146522 0.927587 0.205886 11.00000 0.04947 0.04177 = 0.03263 -0.00619 0.00214 0.00037 AFIX 43 H26 2 0.152616 0.996243 0.247410 11.00000 -1.20000 AFIX 0 C28 1 0.248722 0.804458 0.162968 11.00000 0.06383 0.05007 = 0.06703 -0.00310 0.01987 0.01009 C7 1 0.094665 1.004870 0.237467 11.00000 0.04448 0.04461 = 0.03286 0.00022 -0.00186 -0.00105 C27 1 0.198398 0.864745 0.180155 11.00000 0.06064 0.04709 = 0.05273 -0.00613 0.01122 -0.00153 AFIX 43 H27 2 0.203658 0.936279 0.221299 11.00000 -1.20000 AFIX 0 C9 1 0.075648 1.109877 0.370795 11.00000 0.04375 0.04433 = 0.02924 -0.00216 -0.00642 0.00688 C21 1 0.117020 0.911629 0.189891 11.00000 0.04780 0.03984 = 0.03287 0.00297 -0.00101 0.00790 C23 1 0.128744 0.726200 0.081929 11.00000 0.07354 0.05602 = 0.03647 -0.01561 -0.00152 0.00362 AFIX 43 H23 2 0.122524 0.660010 0.039530 11.00000 -1.20000 AFIX 0 C8 1 0.094537 1.002445 0.320226 11.00000 0.04212 0.04563 = 0.03068 -0.00164 -0.00002 0.00055 C25 1 0.167770 0.842627 0.161003 11.00000 0.05154 0.04346 = 0.04039 -0.00091 0.00693 0.00541 C29 1 0.268939 0.717389 0.117513 11.00000 0.05831 0.09809 = 0.06660 -0.02210 0.01247 0.02195 AFIX 43 H29 2 0.262223 0.654956 0.074239 11.00000 -1.20000 AFIX 0 C2 1 0.043281 1.093933 0.200890 11.00000 0.04133 0.04921 = 0.04326 0.00316 0.00122 -0.00130 AFIX 43 H2 2 0.035934 1.030529 0.242745 11.00000 -1.20000 AFIX 0 C30 1 0.297206 0.720418 0.133679 11.00000 0.07119 0.10016 = 0.06701 -0.01420 0.01931 0.03155 AFIX 43 H30 2 0.309827 0.659344 0.101905 11.00000 -1.20000 AFIX 0 C15 1 0.113622 0.894558 0.369555 11.00000 0.04720 0.04401 = 0.03364 0.00366 0.00290 0.00802 C22 1 0.108214 0.810806 0.127233 11.00000 0.05948 0.06055 = 0.03609 -0.00612 -0.00744 0.00894 AFIX 43 H22 2 0.088366 0.799537 0.115315 11.00000 -1.20000 AFIX 0 C14 1 0.075322 1.276489 0.359914 11.00000 0.06505 0.04757 = 0.04787 -0.00623 0.00213 -0.00486 AFIX 43 H14 2 0.085959 1.322259 0.317694 11.00000 -1.20000 AFIX 0 C24 1 0.157647 0.739340 0.098985 11.00000 0.06204 0.04593 = 0.04411 -0.00835 0.00861 0.00605 C13 1 0.059610 1.372377 0.410429 11.00000 0.07256 0.04621 = 0.06838 -0.01495 -0.00532 0.00923 AFIX 43 H13 2 0.059935 1.483402 0.403142 11.00000 -1.20000 AFIX 0 C12 1 0.043049 1.306578 0.472890 11.00000 0.05702 0.07679 = 0.05248 -0.02297 -0.00775 0.00922 AFIX 43 H12 2 0.032284 1.372949 0.507142 11.00000 -1.20000 AFIX 0 C1 1 0.073594 1.100065 0.187834 11.00000 0.04474 0.03961 = 0.03223 -0.00327 -0.00056 0.00150 C3 1 0.024181 1.181039 0.152272 11.00000 0.04701 0.06257 = 0.06158 0.00447 -0.00443 0.00424 AFIX 43 H3 2 0.004088 1.172833 0.160480 11.00000 -1.20000 AFIX 0 C4 1 0.034786 1.280755 0.091237 11.00000 0.07664 0.05974 = 0.05208 0.01437 -0.01777 0.00161 AFIX 43 H4 2 0.022042 1.343559 0.060274 11.00000 -1.20000 AFIX 0 C5 1 0.064697 1.284895 0.077355 11.00000 0.07504 0.05454 = 0.04329 0.01788 -0.00386 -0.00139 AFIX 43 H5 2 0.072033 1.349718 0.036042 11.00000 -1.20000 AFIX 0 C6 1 0.083599 1.194699 0.123723 11.00000 0.04302 0.05939 = 0.04103 0.00720 0.00237 -0.00360 AFIX 43 H6 2 0.103523 1.196683 0.112162 11.00000 -1.20000 AFIX 0 C16 1 0.131153 0.956348 0.430207 11.00000 0.06292 0.04792 = 0.04367 -0.00307 -0.00690 0.00739 AFIX 43 H16 2 0.131042 1.066552 0.440225 11.00000 -1.20000 AFIX 0 C17 1 0.148944 0.857377 0.476548 11.00000 0.06127 0.08170 = 0.04723 -0.00083 -0.01549 0.00681 AFIX 43 H17 2 0.161040 0.901773 0.516436 11.00000 -1.20000 AFIX 0 C18 1 0.148913 0.694387 0.464225 11.00000 0.07822 0.07139 = 0.05524 0.01819 -0.00680 0.02577 AFIX 43 H18 2 0.161063 0.628850 0.495571 11.00000 -1.20000 AFIX 0 C19 1 0.131250 0.627825 0.406517 11.00000 0.08160 0.05399 = 0.06258 0.01266 -0.00088 0.01812 AFIX 43 H19 2 0.130944 0.516832 0.399087 11.00000 -1.20000 AFIX 0 C20 1 0.113313 0.728508 0.357763 11.00000 0.08330 0.04170 = 0.04520 -0.00040 -0.00660 0.00063 AFIX 43 H20 2 0.101299 0.683754 0.317787 11.00000 -1.20000 AFIX 0 C11 1 0.042736 1.143419 0.483486 11.00000 0.05587 0.08099 = 0.04230 -0.00381 0.00663 0.00518 AFIX 43 H11 2 0.031740 1.098206 0.525144 11.00000 -1.20000 AFIX 0 O4 4 0.009519 0.725176 0.345463 11.00000 0.10031 0.08578 = 0.06609 -0.00502 0.02135 0.03226 AFIX 3 H4A 2 0.020308 0.706516 0.305673 11.00000 -1.50000 H4B 2 -0.006561 0.678616 0.334973 11.00000 -1.50000 AFIX 0 O3 4 0.043423 0.630634 0.217417 11.00000 0.14679 0.10096 = 0.08523 0.00059 0.02463 -0.01119 AFIX 3 H3A 2 0.039923 0.699504 0.253527 11.00000 -1.50000 H3B 2 0.026943 0.608754 0.199027 11.00000 -1.50000 AFIX 0 HKLF 4 1 -1 0 2 -1 0 0 0 -1 0 REM AAAA_a.res in P-1 New: C2/c REM R1 = 0.1541 for 2647 Fo > 4sig(Fo) and 0.2024 for all 4431 data REM 353 parameters refined using 0 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 1.078, deepest hole -0.358, 1-sigma level 0.113 Q1 1 0.2766 0.7575 0.4182 11.00000 0.05 1.08 Q2 1 0.2243 0.8328 0.5474 11.00000 0.05 0.85 Q3 1 0.0000 0.6187 0.2500 10.50000 0.05 0.80 Q4 1 0.2273 0.6262 0.5061 11.00000 0.05 0.71 Q5 1 0.2217 0.7467 0.4050 11.00000 0.05 0.65 Q6 1 -0.0122 0.6796 0.3210 11.00000 0.05 0.50 Q7 1 0.3333 0.7985 0.3101 11.00000 0.05 0.28 Q8 1 0.1674 0.6122 0.5679 11.00000 0.05 0.27 Q9 1 0.0359 1.2357 0.5654 11.00000 0.05 0.27 Q10 1 0.0301 1.3020 0.5643 11.00000 0.05 0.26 Q11 1 0.3294 0.7323 0.3696 11.00000 0.05 0.26 Q12 1 0.3809 0.8104 0.2305 11.00000 0.05 0.25 Q13 1 0.0821 0.5157 0.1749 11.00000 0.05 0.25 Q14 1 0.2728 0.6856 0.3110 11.00000 0.05 0.25 Q15 1 0.0889 0.9672 0.2830 11.00000 0.05 0.24 Q16 1 0.3430 0.7170 0.2698 11.00000 0.05 0.23 Q17 1 0.3111 0.7444 0.3130 11.00000 0.05 0.22 Q18 1 0.3835 0.9222 0.2598 11.00000 0.05 0.22 Q19 1 0.0270 0.5374 0.2116 11.00000 0.05 0.22 Q20 1 0.1036 1.3014 0.2913 11.00000 0.05 0.22 ; _shelx_res_checksum 78848 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 O1 O 0.17754(12) 0.6521(7) 0.0545(3) 0.0782(16) Uani 1 1 d . . . . . H1 H 0.1931 0.7016 0.0524 0.117 Uiso 1 1 d R . . . . O2 O 0.33856(12) 0.8090(7) 0.2105(4) 0.0756(15) Uani 1 1 d . . . . . N1 N 0.21849(12) 0.7891(7) 0.1424(4) 0.0566(13) Uani 1 1 d . . . . . C10 C 0.05865(13) 1.0463(8) 0.4326(3) 0.0486(14) Uani 1 1 d . . . . . H10 H 0.0580 0.9396 0.4395 0.058 Uiso 1 1 d R . . . . C34 C 0.34914(18) 0.8959(14) 0.2772(6) 0.092(3) Uani 1 1 d . . . . . H34A H 0.3432 0.8440 0.3267 0.138 Uiso 1 1 calc GR . . . . H34B H 0.3414 1.0032 0.2757 0.138 Uiso 1 1 calc GR . . . . H34C H 0.3701 0.9001 0.2753 0.138 Uiso 1 1 calc GR . . . . C32 C 0.2887(2) 0.8982(16) 0.2429(9) 0.119(4) Uani 1 1 d . . . . . H32 H 0.2952 0.9581 0.2874 0.143 Uiso 1 1 calc R . . . . C31 C 0.30893(15) 0.8139(8) 0.1980(5) 0.0603(17) Uani 1 1 d . . . . . C33 C 0.25995(19) 0.8968(17) 0.2246(8) 0.119(4) Uani 1 1 d . . . . . H33 H 0.2473 0.9607 0.2548 0.143 Uiso 1 1 calc R . . . . C26 C 0.14652(12) 0.9276(6) 0.2059(3) 0.0413(12) Uani 1 1 d . . . . . H26 H 0.1526 0.9962 0.2474 0.050 Uiso 1 1 calc R . . . . C28 C 0.24872(16) 0.8045(8) 0.1630(4) 0.0602(17) Uani 1 1 d . . . . . C7 C 0.09466(11) 1.0049(6) 0.2375(3) 0.0407(12) Uani 1 1 d . . . . . C27 C 0.19840(15) 0.8647(7) 0.1802(4) 0.0534(15) Uani 1 1 d . . . . . H27 H 0.2037 0.9363 0.2213 0.064 Uiso 1 1 calc R . . . . C9 C 0.07565(11) 1.1099(6) 0.3708(3) 0.0391(12) Uani 1 1 d . . . . . C21 C 0.11702(12) 0.9116(6) 0.1899(3) 0.0402(12) Uani 1 1 d . . . . . C23 C 0.12874(16) 0.7262(8) 0.0819(3) 0.0553(16) Uani 1 1 d . . . . . H23 H 0.1225 0.6600 0.0395 0.066 Uiso 1 1 calc R . . . . C8 C 0.09454(11) 1.0024(7) 0.3202(3) 0.0395(12) Uani 1 1 d . . . . . C25 C 0.16777(13) 0.8426(7) 0.1610(3) 0.0451(13) Uani 1 1 d . . . . . C29 C 0.26894(17) 0.7174(11) 0.1175(5) 0.074(2) Uani 1 1 d . . . . . H29 H 0.2622 0.6550 0.0742 0.089 Uiso 1 1 calc R . . . . C2 C 0.04328(12) 1.0939(7) 0.2009(3) 0.0446(13) Uani 1 1 d . . . . . H2 H 0.0359 1.0305 0.2427 0.054 Uiso 1 1 calc R . . . . C30 C 0.29721(19) 0.7204(12) 0.1337(5) 0.079(2) Uani 1 1 d . . . . . H30 H 0.3098 0.6593 0.1019 0.095 Uiso 1 1 calc R . . . . C15 C 0.11362(12) 0.8946(7) 0.3696(3) 0.0416(12) Uani 1 1 d . . . . . C22 C 0.10821(15) 0.8108(8) 0.1272(3) 0.0521(15) Uani 1 1 d . . . . . H22 H 0.0884 0.7995 0.1153 0.062 Uiso 1 1 calc R . . . . C14 C 0.07532(15) 1.2765(8) 0.3599(4) 0.0535(15) Uani 1 1 d . . . . . H14 H 0.0860 1.3223 0.3177 0.064 Uiso 1 1 calc R . . . . C24 C 0.15765(15) 0.7393(7) 0.0990(4) 0.0507(15) Uani 1 1 d . . . . . C13 C 0.05961(16) 1.3724(8) 0.4104(4) 0.0624(17) Uani 1 1 d . . . . . H13 H 0.0599 1.4834 0.4031 0.075 Uiso 1 1 calc R . . . . C12 C 0.04305(16) 1.3066(9) 0.4729(4) 0.0621(18) Uani 1 1 d . . . . . H12 H 0.0323 1.3729 0.5071 0.075 Uiso 1 1 calc R . . . . C1 C 0.07359(12) 1.1001(6) 0.1878(3) 0.0389(12) Uani 1 1 d . . . . . C3 C 0.02418(14) 1.1810(8) 0.1523(4) 0.0571(16) Uani 1 1 d . . . . . H3 H 0.0041 1.1728 0.1605 0.068 Uiso 1 1 calc R . . . . C4 C 0.03479(18) 1.2808(8) 0.0912(4) 0.0629(18) Uani 1 1 d . . . . . H4 H 0.0220 1.3436 0.0603 0.075 Uiso 1 1 calc R . . . . C5 C 0.06470(17) 1.2849(8) 0.0774(4) 0.0576(16) Uani 1 1 d . . . . . H5 H 0.0720 1.3497 0.0360 0.069 Uiso 1 1 calc R . . . . C6 C 0.08360(13) 1.1947(8) 0.1237(3) 0.0478(14) Uani 1 1 d . . . . . H6 H 0.1035 1.1967 0.1122 0.057 Uiso 1 1 calc R . . . . C16 C 0.13115(14) 0.9563(8) 0.4302(3) 0.0515(14) Uani 1 1 d . . . . . H16 H 0.1310 1.0666 0.4402 0.062 Uiso 1 1 calc R . . . . C17 C 0.14894(16) 0.8574(10) 0.4765(4) 0.0635(18) Uani 1 1 d . . . . . H17 H 0.1610 0.9018 0.5164 0.076 Uiso 1 1 calc R . . . . C18 C 0.14891(18) 0.6944(9) 0.4642(4) 0.068(2) Uani 1 1 d . . . . . H18 H 0.1611 0.6288 0.4956 0.082 Uiso 1 1 calc R . . . . C19 C 0.13125(17) 0.6278(9) 0.4065(4) 0.0661(18) Uani 1 1 d . . . . . H19 H 0.1309 0.5168 0.3991 0.079 Uiso 1 1 calc R . . . . C20 C 0.11331(17) 0.7285(7) 0.3578(4) 0.0568(16) Uani 1 1 d . . . . . H20 H 0.1013 0.6838 0.3178 0.068 Uiso 1 1 calc R . . . . C11 C 0.04274(15) 1.1434(9) 0.4835(4) 0.0597(17) Uani 1 1 d . . . . . H11 H 0.0317 1.0982 0.5251 0.072 Uiso 1 1 calc R . . . . O4 O 0.00952(15) 0.7252(7) 0.3455(3) 0.0840(17) Uani 1 1 d . . . . . H4A H 0.0203 0.7065 0.3057 0.126 Uiso 1 1 d R . . . . H4B H -0.0066 0.6786 0.3350 0.126 Uiso 1 1 d R . . . . O3 O 0.04342(19) 0.6306(9) 0.2174(4) 0.111(2) Uani 1 1 d . . . . . H3A H 0.0399 0.6995 0.2535 0.166 Uiso 1 1 d R . . . . H3B H 0.0269 0.6088 0.1990 0.166 Uiso 1 1 d 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 O1 0.080(3) 0.083(3) 0.072(3) -0.039(3) 0.023(3) 0.008(3) O2 0.059(3) 0.075(3) 0.093(4) 0.005(3) 0.007(3) 0.010(2) N1 0.047(3) 0.058(3) 0.065(3) -0.009(3) 0.012(2) 0.009(2) C10 0.057(3) 0.050(3) 0.038(3) 0.006(2) 0.001(2) 0.006(3) C34 0.058(4) 0.123(8) 0.095(6) -0.014(6) -0.013(4) 0.012(5) C32 0.068(5) 0.140(9) 0.150(9) -0.079(8) 0.002(6) 0.018(6) C31 0.052(4) 0.055(4) 0.074(4) 0.006(3) 0.011(3) 0.016(3) C33 0.059(5) 0.156(10) 0.143(9) -0.084(9) 0.020(6) 0.004(6) C26 0.049(3) 0.042(3) 0.033(2) -0.006(2) 0.002(2) 0.000(2) C28 0.064(4) 0.050(3) 0.067(4) -0.003(3) 0.020(3) 0.010(3) C7 0.044(3) 0.045(3) 0.033(2) 0.000(2) -0.002(2) -0.001(2) C27 0.061(4) 0.047(3) 0.053(3) -0.006(3) 0.011(3) -0.002(3) C9 0.044(3) 0.044(3) 0.029(2) -0.002(2) -0.006(2) 0.007(2) C21 0.048(3) 0.040(3) 0.033(2) 0.003(2) -0.001(2) 0.008(2) C23 0.074(4) 0.056(3) 0.036(3) -0.016(3) -0.002(3) 0.004(3) C8 0.042(3) 0.046(3) 0.031(2) -0.002(2) 0.000(2) 0.001(2) C25 0.052(3) 0.043(3) 0.040(3) -0.001(2) 0.007(2) 0.005(2) C29 0.058(4) 0.098(6) 0.067(4) -0.022(4) 0.012(3) 0.022(4) C2 0.041(3) 0.049(3) 0.043(3) 0.003(2) 0.001(2) -0.001(2) C30 0.071(5) 0.100(6) 0.067(4) -0.014(4) 0.019(4) 0.032(4) C15 0.047(3) 0.044(3) 0.034(2) 0.004(2) 0.003(2) 0.008(2) C22 0.059(4) 0.061(4) 0.036(3) -0.006(3) -0.007(3) 0.009(3) C14 0.065(4) 0.048(3) 0.048(3) -0.006(3) 0.002(3) -0.005(3) C24 0.062(4) 0.046(3) 0.044(3) -0.008(2) 0.009(3) 0.006(3) C13 0.073(4) 0.046(3) 0.068(4) -0.015(3) -0.005(4) 0.009(3) C12 0.057(4) 0.077(5) 0.052(3) -0.023(3) -0.008(3) 0.009(3) C1 0.045(3) 0.040(3) 0.032(2) -0.003(2) -0.001(2) 0.001(2) C3 0.047(3) 0.063(4) 0.062(3) 0.004(3) -0.004(3) 0.004(3) C4 0.077(5) 0.060(4) 0.052(3) 0.014(3) -0.018(3) 0.002(3) C5 0.075(5) 0.055(4) 0.043(3) 0.018(3) -0.004(3) -0.001(3) C6 0.043(3) 0.059(3) 0.041(3) 0.007(3) 0.002(2) -0.004(3) C16 0.063(4) 0.048(3) 0.044(3) -0.003(3) -0.007(3) 0.007(3) C17 0.061(4) 0.082(5) 0.047(3) -0.001(3) -0.015(3) 0.007(4) C18 0.078(5) 0.071(5) 0.055(4) 0.018(3) -0.007(3) 0.026(4) C19 0.082(5) 0.054(4) 0.063(4) 0.013(3) -0.001(4) 0.018(3) C20 0.083(5) 0.042(3) 0.045(3) 0.000(2) -0.007(3) 0.001(3) C11 0.056(4) 0.081(5) 0.042(3) -0.004(3) 0.007(3) 0.005(3) O4 0.100(4) 0.086(4) 0.066(3) -0.005(3) 0.021(3) 0.032(3) O3 0.147(6) 0.101(5) 0.085(4) 0.001(4) 0.025(4) -0.011(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 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 C31 O2 C34 116.1(6) . . ? C27 N1 C28 122.6(6) . . ? C11 C10 C9 121.5(6) . . ? C33 C32 C31 122.2(9) . . ? O2 C31 C32 126.9(8) . . ? O2 C31 C30 117.7(6) . . ? C32 C31 C30 115.4(7) . . ? C32 C33 C28 122.1(8) . . ? C21 C26 C25 121.8(5) . . ? C33 C28 N1 125.7(6) . . ? C33 C28 C29 116.2(7) . . ? C29 C28 N1 118.0(6) . . ? C8 C7 C21 121.3(5) . . ? C8 C7 C1 123.4(5) . . ? C1 C7 C21 115.4(4) . . ? N1 C27 C25 122.0(6) . . ? C10 C9 C8 120.4(5) . . ? C10 C9 C14 117.8(5) . . ? C14 C9 C8 121.8(5) . . ? C26 C21 C7 121.1(5) . . ? C26 C21 C22 118.6(5) . . ? C22 C21 C7 120.2(5) . . ? C24 C23 C22 120.6(5) . . ? C7 C8 C9 123.5(5) . . ? C7 C8 C15 123.2(5) . . ? C15 C8 C9 113.3(4) . . ? C26 C25 C27 119.4(5) . . ? C24 C25 C26 117.4(5) . . ? C24 C25 C27 123.3(5) . . ? C30 C29 C28 122.3(8) . . ? C3 C2 C1 120.8(5) . . ? C29 C30 C31 121.8(7) . . ? C16 C15 C8 120.4(5) . . ? C16 C15 C20 118.4(5) . . ? C20 C15 C8 121.1(5) . . ? C21 C22 C23 120.7(6) . . ? C13 C14 C9 120.6(6) . . ? O1 C24 C25 119.4(6) . . ? C23 C24 O1 119.6(5) . . ? C23 C24 C25 121.0(5) . . ? C14 C13 C12 120.8(6) . . ? C11 C12 C13 119.4(6) . . ? C2 C1 C7 122.2(5) . . ? C6 C1 C7 120.1(5) . . ? C6 C1 C2 117.7(5) . . ? C2 C3 C4 120.5(6) . . ? C5 C4 C3 118.8(6) . . ? C6 C5 C4 120.8(6) . . ? C5 C6 C1 121.4(6) . . ? C15 C16 C17 121.0(6) . . ? C18 C17 C16 120.5(6) . . ? C19 C18 C17 120.4(6) . . ? C18 C19 C20 119.5(7) . . ? C15 C20 C19 120.1(6) . . ? C12 C11 C10 120.0(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 O1 C24 1.375(8) . ? O2 C34 1.395(11) . ? O2 C31 1.367(9) . ? N1 C28 1.424(10) . ? N1 C27 1.276(8) . ? C10 C9 1.386(8) . ? C10 C11 1.372(9) . ? C32 C31 1.376(12) . ? C32 C33 1.345(14) . ? C31 C30 1.413(12) . ? C33 C28 1.367(12) . ? C26 C21 1.376(8) . ? C26 C25 1.411(8) . ? C28 C29 1.393(10) . ? C7 C21 1.503(7) . ? C7 C8 1.359(7) . ? C7 C1 1.484(7) . ? C27 C25 1.442(9) . ? C9 C8 1.496(7) . ? C9 C14 1.395(9) . ? C21 C22 1.384(8) . ? C23 C22 1.390(9) . ? C23 C24 1.351(10) . ? C8 C15 1.486(7) . ? C25 C24 1.407(9) . ? C29 C30 1.315(12) . ? C2 C1 1.402(8) . ? C2 C3 1.382(9) . ? C15 C16 1.373(8) . ? C15 C20 1.393(9) . ? C14 C13 1.358(9) . ? C13 C12 1.390(11) . ? C12 C11 1.366(11) . ? C1 C6 1.393(8) . ? C3 C4 1.389(10) . ? C4 C5 1.385(11) . ? C5 C6 1.370(9) . ? C16 C17 1.380(9) . ? C17 C18 1.369(11) . ? C18 C19 1.358(11) . ? C19 C20 1.415(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 2.01 2.614(8) 130.2 . O4 H4A O3 0.84 1.90 2.733(8) 171.3 . O4 H4B O3 0.85 1.93 2.736(12) 159.9 2 O3 H3A O4 0.84 2.07 2.733(8) 135.8 . O3 H3B O4 0.83 2.05 2.736(12) 139.2 2