#------------------------------------------------------------------------------ #$Date: 2026-06-04 10:23:32 +0100 (Thu, 04 Jun 2026) $ #$Revision: 306202 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577356.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_1577356 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 Br N O' _chemical_formula_sum 'C33 H24 Br N O' _chemical_formula_weight 530.44 _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 100.008(9) _cell_angle_beta 109.515(10) _cell_angle_gamma 91.124(11) _cell_formula_units_Z 2 _cell_length_a 9.341(4) _cell_length_b 12.006(4) _cell_length_c 12.375(5) _cell_measurement_reflns_used 1832 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 28.27 _cell_measurement_theta_min 2.87 _cell_volume 1283.7(9) _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 273.15 _diffrn_measured_fraction_theta_full 0.987 _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 0.1384 _diffrn_reflns_av_unetI/netI 0.2596 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 10091 _diffrn_reflns_point_group_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 24.998 _diffrn_reflns_theta_max 24.998 _diffrn_reflns_theta_min 2.776 _exptl_absorpt_coefficient_mu 1.628 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.372 _exptl_crystal_description BLOCK _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.387 _refine_diff_density_min -0.721 _refine_diff_density_rms 0.086 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 326 _refine_ls_number_reflns 4472 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.964 _refine_ls_R_factor_all 0.2307 _refine_ls_R_factor_gt 0.0875 _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^)+(0.0855P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1817 _refine_ls_wR_factor_ref 0.2333 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1714 _reflns_number_total 4472 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc00735j2.cif _cod_data_source_block aa _cod_original_cell_volume 1283.7(8) _cod_database_code 1577356 _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 0.829 _shelx_estimated_absorpt_t_min 0.792 _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: C22(H22), C27(H27), C2(H2), C10(H10), C14(H14), C6(H6), C20(H20), C16(H16), C25(H25), C4(H4), C26(H26), C17(H17), C3(H3), C13(H13), C11(H11), C5(H5), C12(H12), C31(H31), C19(H19), C18(H18), C32(H32), C29(H29), C30(H30) 2.b Idealised tetrahedral OH refined as rotating group: O1(H1) ; _shelx_res_file ; aa.res created by SHELXL-2014/7 TITL aa_a.res in P-1 REM Old TITL aa_a.res in P-1 REM SHELXT solution in P-1 REM R1 0.258, Rweak 0.080, Alpha 0.077, Orientation as input REM Formula found by SHELXT: C29 N O Br CELL 0.71073 9.3412 12.0065 12.3748 100.008 109.515 91.124 ZERR 2 0.0035 0.0041 0.0045 0.009 0.01 0.011 LATT 1 SFAC C H N O Br UNIT 66 48 2 2 2 L.S. 4 PLAN -69 0 0 SIZE 0.12 0.15 0.12 TEMP 0 HTAB O1 N1 list 4 fmap 2 acta OMIT -3 50 REM REM REM WGHT 0.085500 FVAR 0.62305 BR1 5 0.150064 0.896895 0.991251 11.00000 0.10313 0.07213 = 0.09094 -0.00826 0.06241 -0.01255 O1 4 0.051725 0.643806 0.723962 11.00000 0.03531 0.04751 = 0.10812 -0.00771 0.03955 -0.00269 AFIX 147 H1 2 0.091807 0.706860 0.760045 11.00000 -1.50000 AFIX 0 N1 3 0.261037 0.811453 0.792289 11.00000 0.04150 0.02321 = 0.04697 -0.00400 0.01710 0.00071 C23 1 0.306664 0.623781 0.722331 11.00000 0.02875 0.02256 = 0.02834 0.00115 0.01365 -0.00637 C7 1 0.481172 0.356485 0.625926 11.00000 0.02910 0.02397 = 0.02672 0.00077 0.00665 -0.00180 C8 1 0.627584 0.358622 0.694431 11.00000 0.04582 0.02573 = 0.02323 0.00506 0.01141 -0.00392 C21 1 0.373613 0.436090 0.654417 11.00000 0.02795 0.02203 = 0.03347 -0.00694 0.01851 -0.00486 C1 1 0.409933 0.270119 0.517035 11.00000 0.01838 0.02715 = 0.03383 -0.00042 0.00813 -0.00394 C9 1 0.740978 0.285302 0.660489 11.00000 0.03446 0.01701 = 0.03176 -0.00387 0.00563 -0.00542 C22 1 0.412572 0.551068 0.699232 11.00000 0.02929 0.03040 = 0.03441 -0.00223 0.01517 -0.00746 AFIX 43 H22 2 0.511601 0.580574 0.714308 11.00000 -1.20000 AFIX 0 C15 1 0.694320 0.435919 0.810614 11.00000 0.02111 0.02378 = 0.02696 0.00480 0.00925 -0.00008 C27 1 0.353136 0.742830 0.769219 11.00000 0.02663 0.03078 = 0.03676 -0.00188 0.01257 -0.00489 AFIX 43 H27 2 0.452826 0.769795 0.782807 11.00000 -1.20000 AFIX 0 C2 1 0.410739 0.154477 0.518534 11.00000 0.02713 0.04028 = 0.04016 0.00487 -0.00106 -0.00622 AFIX 43 H2 2 0.462525 0.129764 0.587319 11.00000 -1.20000 AFIX 0 C10 1 0.843029 0.233010 0.743721 11.00000 0.03245 0.03510 = 0.03663 0.00158 0.00297 0.00244 AFIX 43 H10 2 0.839367 0.243493 0.818973 11.00000 -1.20000 AFIX 0 C24 1 0.157933 0.578834 0.702076 11.00000 0.03519 0.04454 = 0.05654 -0.00273 0.03383 0.00505 C33 1 0.256914 0.983158 0.925271 11.00000 0.04246 0.02686 = 0.04480 0.00323 0.01352 0.00239 C14 1 0.755708 0.271200 0.550686 11.00000 0.02756 0.05379 = 0.03615 0.00095 0.00513 -0.00720 AFIX 43 H14 2 0.693361 0.307441 0.493915 11.00000 -1.20000 AFIX 0 C6 1 0.335100 0.302522 0.413992 11.00000 0.04386 0.02530 = 0.04306 -0.00323 0.01450 -0.00479 AFIX 43 H6 2 0.333820 0.379372 0.410998 11.00000 -1.20000 AFIX 0 C20 1 0.637921 0.428982 0.901104 11.00000 0.03745 0.04769 = 0.04369 0.00558 0.01813 -0.01125 AFIX 43 H20 2 0.556283 0.376385 0.887047 11.00000 -1.20000 AFIX 0 C16 1 0.811501 0.517375 0.832361 11.00000 0.02461 0.04326 = 0.03503 0.00963 0.00964 -0.00234 AFIX 43 H16 2 0.851872 0.524252 0.774337 11.00000 -1.20000 AFIX 0 C28 1 0.306118 0.928455 0.835901 11.00000 0.03894 0.03807 = 0.03931 0.00419 0.00730 0.00290 C25 1 0.120210 0.465194 0.658308 11.00000 0.03274 0.03196 = 0.06940 -0.01235 0.03006 -0.02080 AFIX 43 H25 2 0.022035 0.434728 0.644592 11.00000 -1.20000 AFIX 0 C4 1 0.260575 0.110497 0.314881 11.00000 0.04867 0.04805 = 0.03941 -0.02234 -0.00418 -0.00391 AFIX 43 H4 2 0.211022 0.057605 0.247108 11.00000 -1.20000 AFIX 0 C26 1 0.224094 0.396112 0.634554 11.00000 0.03140 0.02522 = 0.06535 -0.00988 0.02277 -0.01643 AFIX 43 H26 2 0.194284 0.319523 0.603989 11.00000 -1.20000 AFIX 0 C17 1 0.869568 0.589250 0.940585 11.00000 0.03437 0.02128 = 0.05455 -0.00918 -0.00141 -0.00893 AFIX 43 H17 2 0.946961 0.645271 0.953928 11.00000 -1.20000 AFIX 0 C3 1 0.334267 0.075802 0.417386 11.00000 0.05758 0.02361 = 0.05549 -0.00394 0.00258 -0.01076 AFIX 43 H3 2 0.333266 -0.001246 0.419527 11.00000 -1.20000 AFIX 0 C13 1 0.863912 0.202759 0.525887 11.00000 0.03392 0.06664 = 0.05302 -0.02094 0.02295 -0.01428 AFIX 43 H13 2 0.871852 0.192353 0.451920 11.00000 -1.20000 AFIX 0 C11 1 0.947962 0.166821 0.716412 11.00000 0.03443 0.03504 = 0.05452 -0.00267 -0.01314 0.00166 AFIX 43 H11 2 1.013551 0.132077 0.773017 11.00000 -1.20000 AFIX 0 C5 1 0.260774 0.223234 0.313447 11.00000 0.04579 0.05568 = 0.03455 0.00588 -0.00152 0.00906 AFIX 43 H5 2 0.210439 0.247611 0.244174 11.00000 -1.20000 AFIX 0 C12 1 0.957979 0.151051 0.608732 11.00000 0.03365 0.03803 = 0.06178 -0.01913 0.00304 0.00371 AFIX 43 H12 2 1.029082 0.104898 0.591121 11.00000 -1.20000 AFIX 0 C31 1 0.375862 1.159753 0.927969 11.00000 0.08722 0.02730 = 0.06061 -0.00618 0.00697 0.00232 AFIX 43 H31 2 0.402634 1.236494 0.959593 11.00000 -1.20000 AFIX 0 C19 1 0.698995 0.497322 1.010434 11.00000 0.04569 0.05450 = 0.03525 0.00471 0.01340 0.00381 AFIX 43 H19 2 0.663169 0.488539 1.070371 11.00000 -1.20000 AFIX 0 C18 1 0.813887 0.578403 1.027926 11.00000 0.04997 0.04741 = 0.03925 -0.00715 0.00984 0.00485 AFIX 43 H18 2 0.854692 0.626796 1.100149 11.00000 -1.20000 AFIX 0 C32 1 0.292243 1.097080 0.971630 11.00000 0.06369 0.02916 = 0.05483 -0.00319 0.00616 0.01292 AFIX 43 H32 2 0.259679 1.131006 1.031866 11.00000 -1.20000 AFIX 0 C29 1 0.385788 0.993569 0.790423 11.00000 0.09452 0.03292 = 0.05991 -0.00200 0.03708 -0.01465 AFIX 43 H29 2 0.416193 0.960290 0.728809 11.00000 -1.20000 AFIX 0 C30 1 0.420845 1.108275 0.835934 11.00000 0.08580 0.04237 = 0.07683 0.01945 0.02464 -0.02033 AFIX 43 H30 2 0.475051 1.151560 0.804776 11.00000 -1.20000 AFIX 0 HKLF 4 REM aa_a.res in P-1 REM R1 = 0.0875 for 1714 Fo > 4sig(Fo) and 0.2307 for all 4472 data REM 326 parameters refined using 0 restraints END WGHT 0.0855 0.0000 REM Highest difference peak 0.387, deepest hole -0.721, 1-sigma level 0.086 Q1 1 0.1262 1.0023 0.9425 11.00000 0.05 0.39 Q2 1 0.0914 0.9968 1.0169 11.00000 0.05 0.33 Q3 1 0.1585 0.9420 0.8276 11.00000 0.05 0.32 Q4 1 0.1160 0.8678 0.9041 11.00000 0.05 0.32 Q5 1 0.3072 0.8332 0.8791 11.00000 0.05 0.31 Q6 1 0.2623 0.3828 0.4259 11.00000 0.05 0.31 Q7 1 0.1489 0.9486 1.0975 11.00000 0.05 0.30 Q8 1 -0.0219 0.9756 0.8978 11.00000 0.05 0.29 Q9 1 0.7403 0.6607 1.0811 11.00000 0.05 0.29 Q10 1 0.7885 0.3322 0.7431 11.00000 0.05 0.29 Q11 1 0.1983 0.9243 1.0846 11.00000 0.05 0.29 Q12 1 0.6012 0.5025 0.9225 11.00000 0.05 0.28 Q13 1 0.4069 0.4059 0.6109 11.00000 0.05 0.28 Q14 1 0.2294 0.8362 0.9430 11.00000 0.05 0.28 Q15 1 0.9856 0.6479 0.8996 11.00000 0.05 0.28 Q16 1 0.2795 1.0863 1.0826 11.00000 0.05 0.28 Q17 1 0.2309 1.1909 0.8808 11.00000 0.05 0.28 Q18 1 0.4719 0.4399 0.4758 11.00000 0.05 0.27 Q19 1 0.4529 0.4272 0.9204 11.00000 0.05 0.27 Q20 1 0.0315 0.9667 0.5228 11.00000 0.05 0.27 Q21 1 0.2355 1.1707 0.9758 11.00000 0.05 0.27 Q22 1 0.3494 0.8338 0.7982 11.00000 0.05 0.27 Q23 1 0.2804 0.3024 0.2186 11.00000 0.05 0.27 Q24 1 0.9839 0.0977 0.6836 11.00000 0.05 0.26 Q25 1 0.8569 0.1175 0.7088 11.00000 0.05 0.26 Q26 1 -0.0031 0.9406 0.9977 11.00000 0.05 0.25 Q27 1 0.0523 0.8698 1.0028 11.00000 0.05 0.25 Q28 1 0.2439 0.8667 0.7987 11.00000 0.05 0.25 Q29 1 0.7026 0.4241 0.9665 11.00000 0.05 0.25 Q30 1 0.3292 0.1957 0.5067 11.00000 0.05 0.25 Q31 1 0.3077 0.0726 0.3406 11.00000 0.05 0.25 Q32 1 0.6238 0.3465 0.9172 11.00000 0.05 0.24 Q33 1 0.4044 0.6572 0.7280 11.00000 0.05 0.24 Q34 1 0.9056 0.2009 0.5891 11.00000 0.05 0.23 Q35 1 0.2388 1.0803 0.8764 11.00000 0.05 0.23 Q36 1 0.6279 0.3883 0.8161 11.00000 0.05 0.23 Q37 1 0.2926 0.5633 0.4179 11.00000 0.05 0.23 Q38 1 0.1793 0.7979 1.0943 11.00000 0.05 0.22 Q39 1 0.3578 0.1800 0.3204 11.00000 0.05 0.22 Q40 1 0.7641 0.6639 0.8968 11.00000 0.05 0.22 Q41 1 0.8207 0.6006 0.8580 11.00000 0.05 0.22 Q42 1 0.3566 0.6968 0.6138 11.00000 0.05 0.22 Q43 1 0.2216 0.7454 0.5982 11.00000 0.05 0.22 Q44 1 0.8048 0.5342 0.9754 11.00000 0.05 0.22 Q45 1 0.8218 0.6654 0.9449 11.00000 0.05 0.22 Q46 1 0.0483 0.2365 0.2939 11.00000 0.05 0.22 Q47 1 0.3786 0.4820 0.8409 11.00000 0.05 0.21 Q48 1 0.3651 0.0182 0.4535 11.00000 0.05 0.21 Q49 1 0.1387 0.0428 0.2821 11.00000 0.05 0.21 Q50 1 0.3427 0.5234 0.4849 11.00000 0.05 0.21 Q51 1 0.3095 0.6900 0.7220 11.00000 0.05 0.21 Q52 1 0.8298 0.4881 1.0289 11.00000 0.05 0.21 Q53 1 0.1494 0.3524 0.6756 11.00000 0.05 0.21 Q54 1 0.2997 0.8725 0.9868 11.00000 0.05 0.21 Q55 1 0.8020 0.3646 0.9433 11.00000 0.05 0.21 Q56 1 0.8587 0.5881 1.1672 11.00000 0.05 0.21 Q57 1 0.2940 0.6004 0.6584 11.00000 0.05 0.21 Q58 1 0.9466 0.1804 0.8436 11.00000 0.05 0.21 Q59 1 0.2927 0.1026 0.3634 11.00000 0.05 0.21 Q60 1 0.3566 0.6376 0.8002 11.00000 0.05 0.21 Q61 1 0.0705 0.2367 0.4879 11.00000 0.05 0.21 Q62 1 0.2549 0.4183 0.7223 11.00000 0.05 0.21 Q63 1 0.1379 0.0992 0.5230 11.00000 0.05 0.21 Q64 1 0.3458 0.4019 0.3292 11.00000 0.05 0.20 Q65 1 0.1903 0.3840 0.5674 11.00000 0.05 0.20 Q66 1 0.1272 0.1556 0.0904 11.00000 0.05 0.20 Q67 1 0.3261 0.5164 0.7181 11.00000 0.05 0.20 Q68 1 0.1629 0.4998 0.7239 11.00000 0.05 0.20 Q69 1 0.7203 0.7200 1.0396 11.00000 0.05 0.20 ; _shelx_res_checksum 26363 _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 Br1 Br 0.15006(15) 0.89690(9) 0.99125(10) 0.0846(5) Uani 1 1 d . . . . . O1 O 0.0517(6) 0.6438(5) 0.7240(6) 0.0628(19) Uani 1 1 d . . . . . H1 H 0.0918 0.7069 0.7600 0.094 Uiso 1 1 calc GR . . . . N1 N 0.2610(8) 0.8115(5) 0.7923(5) 0.0381(17) Uani 1 1 d . . . . . C23 C 0.3067(9) 0.6238(6) 0.7223(6) 0.0262(18) Uani 1 1 d . . . . . C7 C 0.4812(9) 0.3565(6) 0.6259(6) 0.0279(19) Uani 1 1 d . . . . . C8 C 0.6276(10) 0.3586(6) 0.6944(6) 0.032(2) Uani 1 1 d . . . . . C21 C 0.3736(9) 0.4361(6) 0.6544(6) 0.0274(19) Uani 1 1 d . . . . . C1 C 0.4099(8) 0.2701(6) 0.5170(7) 0.0275(19) Uani 1 1 d . . . . . C9 C 0.7410(9) 0.2853(6) 0.6605(7) 0.030(2) Uani 1 1 d . . . . . C22 C 0.4126(9) 0.5511(6) 0.6992(6) 0.031(2) Uani 1 1 d . . . . . H22 H 0.5116 0.5806 0.7143 0.038 Uiso 1 1 calc R . . . . C15 C 0.6943(9) 0.4359(6) 0.8106(6) 0.0237(18) Uani 1 1 d . . . . . C27 C 0.3531(9) 0.7428(6) 0.7692(6) 0.032(2) Uani 1 1 d . . . . . H27 H 0.4528 0.7698 0.7828 0.039 Uiso 1 1 calc R . . . . C2 C 0.4107(9) 0.1545(7) 0.5185(7) 0.040(2) Uani 1 1 d . . . . . H2 H 0.4625 0.1298 0.5873 0.047 Uiso 1 1 calc R . . . . C10 C 0.8430(9) 0.2330(6) 0.7437(7) 0.038(2) Uani 1 1 d . . . . . H10 H 0.8394 0.2435 0.8190 0.045 Uiso 1 1 calc R . . . . C24 C 0.1579(10) 0.5788(7) 0.7021(7) 0.042(2) Uani 1 1 d . . . . . C33 C 0.2569(9) 0.9832(6) 0.9253(7) 0.039(2) Uani 1 1 d . . . . . C14 C 0.7557(9) 0.2712(7) 0.5507(7) 0.042(2) Uani 1 1 d . . . . . H14 H 0.6934 0.3074 0.4939 0.050 Uiso 1 1 calc R . . . . C6 C 0.3351(9) 0.3025(6) 0.4140(7) 0.039(2) Uani 1 1 d . . . . . H6 H 0.3338 0.3794 0.4110 0.047 Uiso 1 1 calc R . . . . C20 C 0.6379(10) 0.4290(7) 0.9011(7) 0.042(2) Uani 1 1 d . . . . . H20 H 0.5563 0.3764 0.8870 0.051 Uiso 1 1 calc R . . . . C16 C 0.8115(9) 0.5174(6) 0.8324(6) 0.034(2) Uani 1 1 d . . . . . H16 H 0.8519 0.5243 0.7743 0.041 Uiso 1 1 calc R . . . . C28 C 0.3061(10) 0.9285(7) 0.8359(7) 0.041(2) Uani 1 1 d . . . . . C25 C 0.1202(10) 0.4652(6) 0.6583(7) 0.045(2) Uani 1 1 d . . . . . H25 H 0.0220 0.4347 0.6446 0.054 Uiso 1 1 calc R . . . . C4 C 0.2606(10) 0.1105(8) 0.3149(8) 0.054(3) Uani 1 1 d . . . . . H4 H 0.2110 0.0576 0.2471 0.065 Uiso 1 1 calc R . . . . C26 C 0.2241(9) 0.3961(6) 0.6346(7) 0.042(2) Uani 1 1 d . . . . . H26 H 0.1943 0.3195 0.6040 0.050 Uiso 1 1 calc R . . . . C17 C 0.8696(10) 0.5893(6) 0.9406(7) 0.043(2) Uani 1 1 d . . . . . H17 H 0.9470 0.6453 0.9539 0.052 Uiso 1 1 calc R . . . . C3 C 0.3343(10) 0.0758(7) 0.4174(8) 0.052(3) Uani 1 1 d . . . . . H3 H 0.3333 -0.0012 0.4195 0.062 Uiso 1 1 calc R . . . . C13 C 0.8639(10) 0.2028(7) 0.5259(8) 0.054(3) Uani 1 1 d . . . . . H13 H 0.8719 0.1924 0.4519 0.064 Uiso 1 1 calc R . . . . C11 C 0.9480(10) 0.1668(7) 0.7164(8) 0.050(3) Uani 1 1 d . . . . . H11 H 1.0136 0.1321 0.7730 0.060 Uiso 1 1 calc R . . . . C5 C 0.2608(10) 0.2232(8) 0.3134(7) 0.050(3) Uani 1 1 d . . . . . H5 H 0.2104 0.2476 0.2442 0.059 Uiso 1 1 calc R . . . . C12 C 0.9580(10) 0.1511(7) 0.6087(9) 0.052(3) Uani 1 1 d . . . . . H12 H 1.0291 0.1049 0.5911 0.062 Uiso 1 1 calc R . . . . C31 C 0.3759(12) 1.1598(8) 0.9280(9) 0.065(3) Uani 1 1 d . . . . . H31 H 0.4026 1.2365 0.9596 0.078 Uiso 1 1 calc R . . . . C19 C 0.6990(11) 0.4973(7) 1.0104(7) 0.046(2) Uani 1 1 d . . . . . H19 H 0.6632 0.4885 1.0704 0.055 Uiso 1 1 calc R . . . . C18 C 0.8139(11) 0.5784(8) 1.0279(7) 0.049(3) Uani 1 1 d . . . . . H18 H 0.8547 0.6268 1.1001 0.059 Uiso 1 1 calc R . . . . C32 C 0.2922(11) 1.0971(7) 0.9716(8) 0.054(3) Uani 1 1 d . . . . . H32 H 0.2597 1.1310 1.0319 0.065 Uiso 1 1 calc R . . . . C29 C 0.3858(12) 0.9936(7) 0.7904(8) 0.061(3) Uani 1 1 d . . . . . H29 H 0.4162 0.9603 0.7288 0.074 Uiso 1 1 calc R . . . . C30 C 0.4208(12) 1.1083(8) 0.8359(9) 0.068(3) Uani 1 1 d . . . . . H30 H 0.4751 1.1516 0.8048 0.082 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 Br1 0.1031(11) 0.0721(8) 0.0909(9) -0.0083(6) 0.0624(8) -0.0126(7) O1 0.035(4) 0.048(4) 0.108(6) -0.008(4) 0.040(4) -0.003(3) N1 0.042(5) 0.023(4) 0.047(4) -0.004(3) 0.017(4) 0.001(4) C23 0.029(5) 0.023(4) 0.028(5) 0.001(3) 0.014(4) -0.006(4) C7 0.029(5) 0.024(4) 0.027(5) 0.001(4) 0.007(4) -0.002(4) C8 0.046(6) 0.026(4) 0.023(5) 0.005(4) 0.011(4) -0.004(4) C21 0.028(5) 0.022(4) 0.033(5) -0.007(3) 0.019(4) -0.005(4) C1 0.018(5) 0.027(5) 0.034(5) 0.000(4) 0.008(4) -0.004(4) C9 0.034(5) 0.017(4) 0.032(5) -0.004(4) 0.006(4) -0.005(4) C22 0.029(5) 0.030(5) 0.034(5) -0.002(4) 0.015(4) -0.007(4) C15 0.021(5) 0.024(4) 0.027(5) 0.005(3) 0.009(4) 0.000(4) C27 0.027(5) 0.031(5) 0.037(5) -0.002(4) 0.013(4) -0.005(4) C2 0.027(5) 0.040(5) 0.040(5) 0.005(4) -0.001(4) -0.006(4) C10 0.032(5) 0.035(5) 0.037(5) 0.002(4) 0.003(4) 0.002(4) C24 0.035(6) 0.045(6) 0.057(6) -0.003(5) 0.034(5) 0.005(5) C33 0.042(6) 0.027(5) 0.045(5) 0.003(4) 0.014(5) 0.002(4) C14 0.028(5) 0.054(6) 0.036(5) 0.001(4) 0.005(4) -0.007(5) C6 0.044(6) 0.025(5) 0.043(6) -0.003(4) 0.014(5) -0.005(4) C20 0.037(6) 0.048(6) 0.044(6) 0.006(5) 0.018(5) -0.011(5) C16 0.025(5) 0.043(5) 0.035(5) 0.010(4) 0.010(4) -0.002(4) C28 0.039(6) 0.038(5) 0.039(5) 0.004(4) 0.007(5) 0.003(5) C25 0.033(6) 0.032(5) 0.069(6) -0.012(4) 0.030(5) -0.021(4) C4 0.049(7) 0.048(6) 0.039(6) -0.022(5) -0.004(5) -0.004(5) C26 0.031(6) 0.025(5) 0.065(6) -0.010(4) 0.023(5) -0.016(4) C17 0.034(6) 0.021(5) 0.055(6) -0.009(4) -0.001(5) -0.009(4) C3 0.058(7) 0.024(5) 0.055(7) -0.004(5) 0.003(5) -0.011(5) C13 0.034(6) 0.067(7) 0.053(6) -0.021(5) 0.023(5) -0.014(5) C11 0.034(6) 0.035(5) 0.055(6) -0.003(5) -0.013(5) 0.002(5) C5 0.046(6) 0.056(6) 0.035(6) 0.006(5) -0.002(5) 0.009(5) C12 0.034(6) 0.038(5) 0.062(7) -0.019(5) 0.003(5) 0.004(5) C31 0.087(9) 0.027(6) 0.061(7) -0.006(5) 0.007(7) 0.002(6) C19 0.046(6) 0.055(6) 0.035(6) 0.005(5) 0.013(5) 0.004(5) C18 0.050(7) 0.047(6) 0.039(6) -0.007(5) 0.010(5) 0.005(5) C32 0.064(8) 0.029(6) 0.055(6) -0.003(5) 0.006(5) 0.013(5) C29 0.095(9) 0.033(6) 0.060(7) -0.002(5) 0.037(6) -0.015(6) C30 0.086(9) 0.042(6) 0.077(8) 0.019(6) 0.025(7) -0.020(6) 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' Br Br -0.2901 2.4595 '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 121.3(7) . . ? C22 C23 C27 119.5(7) . . ? C22 C23 C24 119.2(7) . . ? C24 C23 C27 121.3(7) . . ? C8 C7 C21 123.3(7) . . ? C8 C7 C1 122.9(6) . . ? C21 C7 C1 113.8(7) . . ? C7 C8 C9 123.4(7) . . ? C7 C8 C15 123.0(7) . . ? C15 C8 C9 113.6(7) . . ? C22 C21 C7 123.5(7) . . ? C22 C21 C26 116.8(6) . . ? C26 C21 C7 119.7(7) . . ? C2 C1 C7 121.3(7) . . ? C6 C1 C7 120.6(7) . . ? C6 C1 C2 118.0(7) . . ? C10 C9 C8 119.5(7) . . ? C14 C9 C8 123.2(7) . . ? C14 C9 C10 117.2(7) . . ? C21 C22 C23 121.7(7) . . ? C20 C15 C8 120.9(7) . . ? C16 C15 C8 121.5(7) . . ? C16 C15 C20 117.6(7) . . ? N1 C27 C23 121.5(7) . . ? C3 C2 C1 120.1(8) . . ? C11 C10 C9 121.1(8) . . ? O1 C24 C23 122.1(7) . . ? O1 C24 C25 119.0(8) . . ? C25 C24 C23 118.9(7) . . ? C28 C33 Br1 119.2(6) . . ? C32 C33 Br1 118.5(7) . . ? C32 C33 C28 122.2(8) . . ? C9 C14 C13 120.0(8) . . ? C1 C6 C5 121.3(7) . . ? C19 C20 C15 122.5(8) . . ? C15 C16 C17 120.2(7) . . ? C33 C28 N1 117.9(8) . . ? C29 C28 N1 124.0(7) . . ? C29 C28 C33 117.9(8) . . ? C26 C25 C24 121.1(8) . . ? C5 C4 C3 119.0(8) . . ? C25 C26 C21 122.4(7) . . ? C18 C17 C16 120.6(9) . . ? C4 C3 C2 120.7(8) . . ? C12 C13 C14 120.7(8) . . ? C12 C11 C10 121.0(8) . . ? C4 C5 C6 120.8(8) . . ? C11 C12 C13 119.9(8) . . ? C32 C31 C30 119.8(9) . . ? C18 C19 C20 118.0(8) . . ? C19 C18 C17 121.0(8) . . ? C31 C32 C33 119.1(9) . . ? C28 C29 C30 120.3(9) . . ? C29 C30 C31 120.7(9) . . ? 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 Br1 C33 1.880(8) . ? O1 C24 1.343(8) . ? N1 C27 1.269(8) . ? N1 C28 1.415(9) . ? C23 C22 1.400(9) . ? C23 C27 1.445(9) . ? C23 C24 1.405(10) . ? C7 C8 1.344(10) . ? C7 C21 1.485(9) . ? C7 C1 1.491(10) . ? C8 C9 1.510(10) . ? C8 C15 1.494(10) . ? C21 C22 1.387(9) . ? C21 C26 1.395(10) . ? C1 C2 1.392(10) . ? C1 C6 1.361(9) . ? C9 C10 1.399(9) . ? C9 C14 1.393(10) . ? C15 C20 1.401(9) . ? C15 C16 1.377(9) . ? C2 C3 1.391(10) . ? C10 C11 1.366(10) . ? C24 C25 1.370(10) . ? C33 C28 1.402(10) . ? C33 C32 1.375(10) . ? C14 C13 1.394(10) . ? C6 C5 1.386(10) . ? C20 C19 1.382(10) . ? C16 C17 1.388(10) . ? C28 C29 1.375(11) . ? C25 C26 1.361(10) . ? C4 C3 1.367(11) . ? C4 C5 1.357(11) . ? C17 C18 1.370(11) . ? C13 C12 1.360(11) . ? C11 C12 1.348(11) . ? C31 C32 1.367(12) . ? C31 C30 1.393(12) . ? C19 C18 1.370(11) . ? C29 C30 1.382(11) . ? 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 1.89 2.596(9) 144.0 .