#------------------------------------------------------------------------------ #$Date: 2020-03-05 01:37:43 +0200 (Thu, 05 Mar 2020) $ #$Revision: 248829 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/70/1557041.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_1557041 loop_ _publ_author_name 'Rottsch\"afer, Dennis' 'Glodde, Timo' 'Neumann, Beate' 'Stammler, Hans-Georg' 'Ghadwal, Rajendra S.' _publ_section_title ; A crystalline C5-protonated 1,3-imidazol-4-ylidene. ; _journal_issue 13 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 2027 _journal_page_last 2030 _journal_paper_doi 10.1039/c9cc09428h _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C39 H45 N2, C H4 O, Br' _chemical_formula_sum 'C40 H49 Br N2 O' _chemical_formula_weight 653.72 _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 2018-04-25 _audit_creation_method ; Olex2 1.2 (compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488) ; _audit_update_record ; 2019-08-14 deposited with the CCDC. 2020-01-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 108.6410(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.10880(10) _cell_length_b 21.1979(2) _cell_length_c 15.9518(2) _cell_measurement_reflns_used 67331 _cell_measurement_temperature 100.0(1) _cell_measurement_theta_max 31.7600 _cell_measurement_theta_min 1.9140 _cell_volume 3559.32(7) _computing_cell_refinement 'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)' _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 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.0(1) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.0951 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 6.00 95.00 1.00 11.00 -- 25.96 57.00 30.00 89 2 \w 6.00 95.00 1.00 11.00 -- 25.96 57.00-180.00 89 3 \w 6.00 95.00 1.00 11.00 -- 25.96 57.00 120.00 89 4 \w 12.00 95.00 1.00 11.00 -- 25.96-143.00-120.00 83 5 \w -43.00 47.00 1.00 11.00 -- 25.96 -57.00 30.00 90 6 \w -46.00 51.00 1.00 11.00 -- 25.96 -38.00 120.00 97 7 \w -4.00 96.00 1.00 11.00 -- 25.96 77.00-150.00 100 8 \w -20.00 68.00 1.00 11.00 -- 25.96 -99.00 -30.00 88 9 \w 0.00 98.00 1.00 11.00 -- 25.96 38.00 -60.00 98 10 \w -4.00 96.00 1.00 11.00 -- 25.96 77.00 -60.00 100 11 \w -43.00 47.00 1.00 11.00 -- 25.96 -57.00-120.00 90 12 \w -49.00 49.00 1.00 11.00 -- -23.50 38.00 30.00 98 13 \w 35.00 102.00 1.00 11.00 -- 25.96 178.00 90.00 67 14 \w -47.00 99.00 1.00 11.00 -- 25.96 0.00-120.00 146 15 \w -4.00 96.00 1.00 11.00 -- 25.96 77.00-180.00 100 16 \w -47.00 99.00 1.00 11.00 -- 25.96 0.00-180.00 146 17 \w -47.00 99.00 1.00 11.00 -- 25.96 0.00-150.00 146 18 \w -4.00 96.00 1.00 11.00 -- 25.96 77.00 60.00 100 19 \w -47.00 99.00 1.00 11.00 -- 25.96 0.00 -90.00 146 20 \w -47.00 99.00 1.00 11.00 -- 25.96 0.00 -60.00 146 21 \w -20.00 68.00 1.00 11.00 -- 25.96 -99.00 90.00 88 22 \w -47.00 67.00 1.00 11.00 -- 25.96 0.00 0.00 114 23 \w -47.00 99.00 1.00 11.00 -- 25.96 0.00 -30.00 146 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Single source at offset/far, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0611565000 _diffrn_orient_matrix_UB_12 -0.0012701000 _diffrn_orient_matrix_UB_13 -0.0322055000 _diffrn_orient_matrix_UB_21 0.0007125000 _diffrn_orient_matrix_UB_22 -0.0333799000 _diffrn_orient_matrix_UB_23 0.0031564000 _diffrn_orient_matrix_UB_31 -0.0282984000 _diffrn_orient_matrix_UB_32 0.0018971000 _diffrn_orient_matrix_UB_33 0.0339818000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_unetI/netI 0.0137 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 206381 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.080 _diffrn_reflns_theta_min 1.655 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 1.187 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.563 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.220 _exptl_crystal_description irregular _exptl_crystal_F_000 1384 _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.245 _exptl_crystal_size_min 0.212 _refine_diff_density_max 0.455 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 407 _refine_ls_number_reflns 10453 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0302 _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^)+(0.0357P)^2^+2.1231P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0775 _refine_ls_wR_factor_ref 0.0800 _reflns_Friedel_coverage 0.000 _reflns_number_gt 9367 _reflns_number_total 10453 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc09428h2.cif _cod_data_source_block compound1 _cod_depositor_comments 'Adding full bibliography for 1557041--1557044.cif.' _cod_database_code 1557041 _shelx_shelxl_version_number 2016/6 _chemical_oxdiff_formula 'C40 H49 Br N2 O' _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 0.787 _shelx_estimated_absorpt_t_min 0.642 _reflns_odcompleteness_completeness 99.97 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 30.01 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C10(H10), C13(H13), C22(H22), C25(H25) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20), C29(H29), C30(H30), C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39) 2.c Idealised Me refined as rotating group: C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B, H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A, H27B,H27C), C40(H40A,H40B,H40C) 2.d Idealised tetrahedral OH refined as rotating group: O1(H1) ; _shelx_res_file ; TITL rottschaefer83_a.res in P2(1)/n rottschaefer83.res created by SHELXL-2016/6 at 15:10:46 on 25-Apr-2018 REM Old TITL rottschaefer83 in P2/n REM SHELXT solution in P2(1)/n REM R1 0.109, Rweak 0.038, Alpha 0.036, Orientation as input REM Formula found by SHELXT: C13 N3 Br CELL 0.71073 11.1088 21.1979 15.9518 90 108.641 90 ZERR 4 0.0001 0.0002 0.0002 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Br N O UNIT 160 196 4 8 4 L.S. 11 PLAN 5 SIZE 0.212 0.245 0.41 TEMP -173.15(10) BOND $H LIST more -1 conf fmap 2 acta OMIT 6 0 6 OMIT -6 12 6 OMIT -3 15 3 OMIT 0 24 0 OMIT -3 3 3 OMIT 6 0 0 OMIT 3 0 9 OMIT -12 6 3 REM REM REM WGHT 0.035700 2.123100 FVAR 2.65574 BR1 3 0.379260 0.133478 0.336766 11.00000 0.01412 0.02513 = 0.02788 0.00074 -0.00099 -0.00322 O1 5 0.549481 0.088100 0.217194 11.00000 0.02332 0.03765 = 0.03336 -0.00324 0.00706 -0.00837 AFIX 147 H1 2 0.511702 0.106379 0.248300 11.00000 -1.50000 AFIX 0 N1 4 0.546054 0.339849 0.332733 11.00000 0.01416 0.01232 = 0.00911 0.00063 0.00351 0.00024 N2 4 0.450337 0.341717 0.190706 11.00000 0.01312 0.01169 = 0.00965 -0.00022 0.00346 -0.00090 C1 1 0.506929 0.378311 0.261566 11.00000 0.01095 0.01306 = 0.00879 0.00054 0.00363 0.00014 C2 1 0.511293 0.278373 0.306562 11.00000 0.01795 0.01218 = 0.01486 0.00120 0.00560 -0.00005 AFIX 43 H2 2 0.526320 0.242241 0.343715 11.00000 -1.20000 AFIX 0 C3 1 0.451845 0.279462 0.218036 11.00000 0.01778 0.01153 = 0.01430 -0.00032 0.00578 -0.00160 AFIX 43 H3 2 0.417563 0.244189 0.181458 11.00000 -1.20000 AFIX 0 C4 1 0.591708 0.359731 0.424780 11.00000 0.01529 0.01376 = 0.00798 0.00088 0.00286 0.00026 C5 1 0.722589 0.361035 0.469638 11.00000 0.01445 0.01527 = 0.01274 0.00275 0.00322 0.00015 C6 1 0.760750 0.378712 0.558718 11.00000 0.01920 0.02116 = 0.01312 0.00121 0.00007 -0.00192 AFIX 43 H6 2 0.848732 0.380048 0.591459 11.00000 -1.20000 AFIX 0 C7 1 0.672380 0.394341 0.600152 11.00000 0.02851 0.02392 = 0.01047 -0.00193 0.00349 -0.00164 AFIX 43 H7 2 0.700176 0.406580 0.660615 11.00000 -1.20000 AFIX 0 C8 1 0.543701 0.392135 0.553534 11.00000 0.02563 0.02381 = 0.01409 -0.00024 0.00907 0.00266 AFIX 43 H8 2 0.484173 0.403176 0.582575 11.00000 -1.20000 AFIX 0 C9 1 0.499657 0.374016 0.464721 11.00000 0.01678 0.01704 = 0.01277 0.00225 0.00557 0.00217 C10 1 0.820866 0.341045 0.427209 11.00000 0.01471 0.02079 = 0.01704 0.00571 0.00586 0.00382 AFIX 13 H10 2 0.780046 0.342004 0.361530 11.00000 -1.20000 AFIX 0 C11 1 0.936588 0.385078 0.451166 11.00000 0.01632 0.03780 = 0.03088 0.00556 0.00639 -0.00249 AFIX 137 H11A 2 0.908011 0.428779 0.438011 11.00000 -1.50000 H11B 2 0.991815 0.373541 0.416436 11.00000 -1.50000 H11C 2 0.983826 0.381029 0.514347 11.00000 -1.50000 AFIX 0 C12 1 0.863682 0.273198 0.454456 11.00000 0.03113 0.02613 = 0.02822 0.01140 0.01489 0.01314 AFIX 137 H12A 2 0.905090 0.271338 0.518642 11.00000 -1.50000 H12B 2 0.923724 0.259694 0.424433 11.00000 -1.50000 H12C 2 0.789594 0.245200 0.437705 11.00000 -1.50000 AFIX 0 C13 1 0.357754 0.368407 0.417921 11.00000 0.01566 0.02616 = 0.01580 0.00290 0.00609 0.00372 AFIX 13 H13 2 0.344908 0.356319 0.355062 11.00000 -1.20000 AFIX 0 C14 1 0.289727 0.430969 0.417447 11.00000 0.02566 0.03143 = 0.05406 0.00784 0.01119 0.01152 AFIX 137 H14A 2 0.299219 0.443426 0.478390 11.00000 -1.50000 H14B 2 0.199324 0.426214 0.384067 11.00000 -1.50000 H14C 2 0.326929 0.463466 0.389579 11.00000 -1.50000 AFIX 0 C15 1 0.301130 0.315966 0.460004 11.00000 0.02027 0.03562 = 0.02997 0.00808 0.00628 -0.00310 AFIX 137 H15A 2 0.339983 0.275499 0.453645 11.00000 -1.50000 H15B 2 0.209190 0.313741 0.430323 11.00000 -1.50000 H15C 2 0.318034 0.325147 0.522936 11.00000 -1.50000 AFIX 0 C16 1 0.397025 0.363002 0.099551 11.00000 0.01390 0.01270 = 0.00775 -0.00094 0.00186 -0.00038 C17 1 0.264434 0.366978 0.063521 11.00000 0.01355 0.01656 = 0.01194 -0.00276 0.00286 -0.00057 C18 1 0.214798 0.387348 -0.024061 11.00000 0.01514 0.01958 = 0.01412 -0.00101 -0.00024 0.00109 AFIX 43 H18 2 0.125400 0.390872 -0.050661 11.00000 -1.20000 AFIX 0 C19 1 0.294173 0.402487 -0.072682 11.00000 0.02175 0.01775 = 0.01198 0.00138 0.00119 0.00089 AFIX 43 H19 2 0.258792 0.416315 -0.132171 11.00000 -1.20000 AFIX 0 C20 1 0.424951 0.397594 -0.035099 11.00000 0.02009 0.01780 = 0.01155 0.00140 0.00567 -0.00093 AFIX 43 H20 2 0.477995 0.408136 -0.069393 11.00000 -1.20000 AFIX 0 C21 1 0.480213 0.377452 0.052255 11.00000 0.01461 0.01216 = 0.01074 -0.00104 0.00369 -0.00070 C22 1 0.173212 0.347922 0.112700 11.00000 0.01357 0.02739 = 0.01471 -0.00316 0.00468 -0.00206 AFIX 13 H22 2 0.223578 0.338715 0.175638 11.00000 -1.20000 AFIX 0 C23 1 0.076906 0.400217 0.111370 11.00000 0.01962 0.03264 = 0.03586 -0.00803 0.01297 -0.00006 AFIX 137 H23A 2 0.122342 0.439326 0.134691 11.00000 -1.50000 H23B 2 0.025200 0.387584 0.148114 11.00000 -1.50000 H23C 2 0.021733 0.407105 0.050457 11.00000 -1.50000 AFIX 0 C24 1 0.102536 0.287639 0.070816 11.00000 0.02497 0.02636 = 0.02219 -0.00192 0.00998 -0.00702 AFIX 137 H24A 2 0.053882 0.295767 0.008733 11.00000 -1.50000 H24B 2 0.044524 0.274841 0.102844 11.00000 -1.50000 H24C 2 0.164119 0.253856 0.074155 11.00000 -1.50000 AFIX 0 C25 1 0.624029 0.372349 0.089107 11.00000 0.01357 0.01721 = 0.01338 0.00032 0.00472 -0.00030 AFIX 13 H25 2 0.646961 0.356441 0.151255 11.00000 -1.20000 AFIX 0 C26 1 0.686306 0.437025 0.091145 11.00000 0.02176 0.02268 = 0.02587 -0.00042 0.00813 -0.00741 AFIX 137 H26A 2 0.666188 0.453218 0.030676 11.00000 -1.50000 H26B 2 0.778606 0.432939 0.117633 11.00000 -1.50000 H26C 2 0.653979 0.466311 0.126432 11.00000 -1.50000 AFIX 0 C27 1 0.674841 0.325249 0.035473 11.00000 0.02006 0.02875 = 0.02079 -0.00408 0.00813 0.00403 AFIX 137 H27A 2 0.637232 0.283649 0.037224 11.00000 -1.50000 H27B 2 0.767473 0.322396 0.060961 11.00000 -1.50000 H27C 2 0.652260 0.339630 -0.026007 11.00000 -1.50000 AFIX 0 C28 1 0.521732 0.446938 0.260748 11.00000 0.01360 0.01200 = 0.00904 -0.00049 0.00426 -0.00054 C29 1 0.420079 0.485265 0.213793 11.00000 0.01260 0.01419 = 0.01278 -0.00104 0.00327 -0.00068 AFIX 43 H29 2 0.340174 0.466760 0.183279 11.00000 -1.20000 AFIX 0 C30 1 0.435208 0.550240 0.211486 11.00000 0.01357 0.01427 = 0.01329 0.00054 0.00383 0.00075 AFIX 43 H30 2 0.365246 0.575701 0.179458 11.00000 -1.20000 AFIX 0 C31 1 0.552159 0.578811 0.255706 11.00000 0.01441 0.01269 = 0.01115 -0.00124 0.00594 -0.00100 C32 1 0.653318 0.539991 0.302965 11.00000 0.01354 0.01543 = 0.01438 -0.00063 0.00262 -0.00181 AFIX 43 H32 2 0.733302 0.558397 0.333532 11.00000 -1.20000 AFIX 0 C33 1 0.638381 0.475037 0.305777 11.00000 0.01340 0.01498 = 0.01438 0.00098 0.00202 0.00002 AFIX 43 H33 2 0.707863 0.449553 0.338500 11.00000 -1.20000 AFIX 0 C34 1 0.567993 0.648358 0.254056 11.00000 0.01729 0.01329 = 0.01182 -0.00095 0.00572 -0.00146 C35 1 0.462515 0.688490 0.236582 11.00000 0.01874 0.01556 = 0.01613 -0.00013 0.00608 -0.00038 AFIX 43 H35 2 0.379825 0.671110 0.224184 11.00000 -1.20000 AFIX 0 C36 1 0.478282 0.753752 0.237297 11.00000 0.02518 0.01590 = 0.01865 0.00088 0.00950 0.00268 AFIX 43 H36 2 0.406233 0.780574 0.225266 11.00000 -1.20000 AFIX 0 C37 1 0.598503 0.779786 0.255465 11.00000 0.03147 0.01363 = 0.02380 -0.00186 0.01389 -0.00284 AFIX 43 H37 2 0.609139 0.824285 0.256992 11.00000 -1.20000 AFIX 0 C38 1 0.703176 0.740294 0.271400 11.00000 0.02452 0.01711 = 0.02599 -0.00418 0.01245 -0.00635 AFIX 43 H38 2 0.785468 0.757980 0.282954 11.00000 -1.20000 AFIX 0 C39 1 0.688743 0.675258 0.270613 11.00000 0.01861 0.01610 = 0.01932 -0.00226 0.00877 -0.00238 AFIX 43 H39 2 0.761100 0.648777 0.281355 11.00000 -1.20000 AFIX 0 C40 1 0.516176 0.023540 0.209313 11.00000 0.02992 0.03478 = 0.06350 -0.00620 0.01675 -0.00184 AFIX 137 H40A 2 0.498676 0.010094 0.147784 11.00000 -1.50000 H40B 2 0.440224 0.017152 0.226909 11.00000 -1.50000 H40C 2 0.586523 -0.001410 0.247779 11.00000 -1.50000 AFIX 0 HKLF 4 REM rottschaefer83_a.res in P2(1)/n REM R1 = 0.0302 for 9367 Fo > 4sig(Fo) and 0.0354 for all 10453 data REM 407 parameters refined using 0 restraints END WGHT 0.0357 2.1231 REM Highest difference peak 0.455, deepest hole -0.372, 1-sigma level 0.052 Q1 1 0.4309 0.5178 0.2153 11.00000 0.05 0.46 Q2 1 0.5182 0.4111 0.2606 11.00000 0.05 0.44 Q3 1 0.6432 0.5081 0.3017 11.00000 0.05 0.43 Q4 1 0.4423 0.3700 0.0772 11.00000 0.05 0.42 Q5 1 0.6953 0.7074 0.2788 11.00000 0.05 0.41 ; _shelx_res_checksum 20867 _olex2_date_sample_data_collection 2018-04-19 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.301 _oxdiff_exptl_absorpt_empirical_full_min 0.900 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 Br1 Br 0.37926(2) 0.13348(2) 0.33677(2) 0.02421(4) Uani 1 1 d . O1 O 0.54948(10) 0.08810(6) 0.21719(8) 0.0319(2) Uani 1 1 d . H1 H 0.511702 0.106379 0.248300 0.048 Uiso 1 1 calc GR N1 N 0.54605(9) 0.33985(4) 0.33273(6) 0.01191(17) Uani 1 1 d . N2 N 0.45034(9) 0.34172(4) 0.19071(6) 0.01153(17) Uani 1 1 d . C1 C 0.50693(10) 0.37831(5) 0.26157(7) 0.01082(19) Uani 1 1 d . C2 C 0.51129(11) 0.27837(5) 0.30656(8) 0.0149(2) Uani 1 1 d . H2 H 0.526320 0.242241 0.343715 0.018 Uiso 1 1 calc R C3 C 0.45185(11) 0.27946(5) 0.21804(8) 0.0144(2) Uani 1 1 d . H3 H 0.417563 0.244189 0.181458 0.017 Uiso 1 1 calc R C4 C 0.59171(11) 0.35973(5) 0.42478(7) 0.01255(19) Uani 1 1 d . C5 C 0.72259(11) 0.36103(5) 0.46964(8) 0.0144(2) Uani 1 1 d . C6 C 0.76075(12) 0.37871(6) 0.55872(8) 0.0190(2) Uani 1 1 d . H6 H 0.848732 0.380048 0.591459 0.023 Uiso 1 1 calc R C7 C 0.67238(13) 0.39434(6) 0.60015(8) 0.0216(2) Uani 1 1 d . H7 H 0.700176 0.406580 0.660615 0.026 Uiso 1 1 calc R C8 C 0.54370(13) 0.39214(6) 0.55353(8) 0.0205(2) Uani 1 1 d . H8 H 0.484173 0.403176 0.582575 0.025 Uiso 1 1 calc R C9 C 0.49966(11) 0.37402(5) 0.46472(8) 0.0153(2) Uani 1 1 d . C10 C 0.82087(11) 0.34104(6) 0.42721(8) 0.0173(2) Uani 1 1 d . H10 H 0.780046 0.342004 0.361530 0.021 Uiso 1 1 calc R C11 C 0.93659(13) 0.38508(8) 0.45117(10) 0.0286(3) Uani 1 1 d . H11A H 0.908011 0.428779 0.438011 0.043 Uiso 1 1 calc GR H11B H 0.991815 0.373541 0.416436 0.043 Uiso 1 1 calc GR H11C H 0.983826 0.381029 0.514347 0.043 Uiso 1 1 calc GR C12 C 0.86368(14) 0.27320(7) 0.45446(10) 0.0272(3) Uani 1 1 d . H12A H 0.905090 0.271338 0.518642 0.041 Uiso 1 1 calc GR H12B H 0.923724 0.259694 0.424433 0.041 Uiso 1 1 calc GR H12C H 0.789594 0.245200 0.437705 0.041 Uiso 1 1 calc GR C13 C 0.35775(12) 0.36841(6) 0.41792(8) 0.0190(2) Uani 1 1 d . H13 H 0.344908 0.356319 0.355062 0.023 Uiso 1 1 calc R C14 C 0.28973(15) 0.43097(8) 0.41745(13) 0.0374(4) Uani 1 1 d . H14A H 0.299219 0.443426 0.478390 0.056 Uiso 1 1 calc GR H14B H 0.199324 0.426214 0.384067 0.056 Uiso 1 1 calc GR H14C H 0.326929 0.463466 0.389579 0.056 Uiso 1 1 calc GR C15 C 0.30113(13) 0.31597(8) 0.46000(10) 0.0290(3) Uani 1 1 d . H15A H 0.339983 0.275499 0.453645 0.044 Uiso 1 1 calc GR H15B H 0.209190 0.313741 0.430323 0.044 Uiso 1 1 calc GR H15C H 0.318034 0.325147 0.522936 0.044 Uiso 1 1 calc GR C16 C 0.39703(11) 0.36300(5) 0.09955(7) 0.01183(19) Uani 1 1 d . C17 C 0.26443(11) 0.36698(5) 0.06352(8) 0.0143(2) Uani 1 1 d . C18 C 0.21480(11) 0.38735(6) -0.02406(8) 0.0174(2) Uani 1 1 d . H18 H 0.125400 0.390872 -0.050661 0.021 Uiso 1 1 calc R C19 C 0.29417(12) 0.40249(6) -0.07268(8) 0.0182(2) Uani 1 1 d . H19 H 0.258792 0.416315 -0.132171 0.022 Uiso 1 1 calc R C20 C 0.42495(12) 0.39759(6) -0.03510(8) 0.0163(2) Uani 1 1 d . H20 H 0.477995 0.408136 -0.069393 0.020 Uiso 1 1 calc R C21 C 0.48021(11) 0.37745(5) 0.05226(7) 0.01259(19) Uani 1 1 d . C22 C 0.17321(11) 0.34792(6) 0.11270(8) 0.0185(2) Uani 1 1 d . H22 H 0.223578 0.338715 0.175638 0.022 Uiso 1 1 calc R C23 C 0.07691(13) 0.40022(7) 0.11137(11) 0.0284(3) Uani 1 1 d . H23A H 0.122342 0.439326 0.134691 0.043 Uiso 1 1 calc GR H23B H 0.025200 0.387584 0.148114 0.043 Uiso 1 1 calc GR H23C H 0.021733 0.407105 0.050457 0.043 Uiso 1 1 calc GR C24 C 0.10254(13) 0.28764(7) 0.07082(9) 0.0239(3) Uani 1 1 d . H24A H 0.053882 0.295767 0.008733 0.036 Uiso 1 1 calc GR H24B H 0.044524 0.274841 0.102844 0.036 Uiso 1 1 calc GR H24C H 0.164119 0.253856 0.074155 0.036 Uiso 1 1 calc GR C25 C 0.62403(11) 0.37235(5) 0.08911(8) 0.0146(2) Uani 1 1 d . H25 H 0.646961 0.356441 0.151255 0.018 Uiso 1 1 calc R C26 C 0.68631(13) 0.43703(6) 0.09115(9) 0.0233(3) Uani 1 1 d . H26A H 0.666188 0.453218 0.030676 0.035 Uiso 1 1 calc GR H26B H 0.778606 0.432939 0.117633 0.035 Uiso 1 1 calc GR H26C H 0.653979 0.466311 0.126432 0.035 Uiso 1 1 calc GR C27 C 0.67484(13) 0.32525(7) 0.03547(9) 0.0228(3) Uani 1 1 d . H27A H 0.637232 0.283649 0.037224 0.034 Uiso 1 1 calc GR H27B H 0.767473 0.322396 0.060961 0.034 Uiso 1 1 calc GR H27C H 0.652260 0.339630 -0.026007 0.034 Uiso 1 1 calc GR C28 C 0.52173(10) 0.44694(5) 0.26075(7) 0.01139(19) Uani 1 1 d . C29 C 0.42008(11) 0.48526(5) 0.21379(7) 0.0134(2) Uani 1 1 d . H29 H 0.340174 0.466760 0.183279 0.016 Uiso 1 1 calc R C30 C 0.43521(11) 0.55024(5) 0.21149(7) 0.0138(2) Uani 1 1 d . H30 H 0.365246 0.575701 0.179458 0.017 Uiso 1 1 calc R C31 C 0.55216(11) 0.57881(5) 0.25571(7) 0.01231(19) Uani 1 1 d . C32 C 0.65332(11) 0.53999(5) 0.30297(8) 0.0149(2) Uani 1 1 d . H32 H 0.733302 0.558397 0.333532 0.018 Uiso 1 1 calc R C33 C 0.63838(11) 0.47504(5) 0.30578(8) 0.0148(2) Uani 1 1 d . H33 H 0.707863 0.449553 0.338500 0.018 Uiso 1 1 calc R C34 C 0.56799(11) 0.64836(5) 0.25406(7) 0.0139(2) Uani 1 1 d . C35 C 0.46251(12) 0.68849(6) 0.23658(8) 0.0167(2) Uani 1 1 d . H35 H 0.379825 0.671110 0.224184 0.020 Uiso 1 1 calc R C36 C 0.47828(13) 0.75375(6) 0.23730(8) 0.0193(2) Uani 1 1 d . H36 H 0.406233 0.780574 0.225266 0.023 Uiso 1 1 calc R C37 C 0.59850(13) 0.77979(6) 0.25546(9) 0.0218(2) Uani 1 1 d . H37 H 0.609139 0.824285 0.256992 0.026 Uiso 1 1 calc R C38 C 0.70318(13) 0.74029(6) 0.27140(9) 0.0215(2) Uani 1 1 d . H38 H 0.785468 0.757980 0.282954 0.026 Uiso 1 1 calc R C39 C 0.68874(12) 0.67526(6) 0.27061(8) 0.0174(2) Uani 1 1 d . H39 H 0.761100 0.648777 0.281355 0.021 Uiso 1 1 calc R C40 C 0.51618(17) 0.02354(8) 0.20931(15) 0.0423(4) Uani 1 1 d . H40A H 0.498676 0.010094 0.147784 0.063 Uiso 1 1 calc GR H40B H 0.440224 0.017152 0.226909 0.063 Uiso 1 1 calc GR H40C H 0.586523 -0.001410 0.247779 0.063 Uiso 1 1 calc GR loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01412(6) 0.02513(7) 0.02788(7) 0.00074(5) -0.00099(5) -0.00322(4) O1 0.0233(5) 0.0376(6) 0.0334(6) -0.0032(5) 0.0071(4) -0.0084(4) N1 0.0142(4) 0.0123(4) 0.0091(4) 0.0006(3) 0.0035(3) 0.0002(3) N2 0.0131(4) 0.0117(4) 0.0096(4) -0.0002(3) 0.0035(3) -0.0009(3) C1 0.0109(4) 0.0131(5) 0.0088(4) 0.0005(4) 0.0036(4) 0.0001(3) C2 0.0179(5) 0.0122(5) 0.0149(5) 0.0012(4) 0.0056(4) -0.0001(4) C3 0.0178(5) 0.0115(5) 0.0143(5) -0.0003(4) 0.0058(4) -0.0016(4) C4 0.0153(5) 0.0138(5) 0.0080(4) 0.0009(4) 0.0029(4) 0.0003(4) C5 0.0145(5) 0.0153(5) 0.0127(5) 0.0028(4) 0.0032(4) 0.0002(4) C6 0.0192(5) 0.0212(6) 0.0131(5) 0.0012(4) 0.0001(4) -0.0019(4) C7 0.0285(6) 0.0239(6) 0.0105(5) -0.0019(4) 0.0035(5) -0.0016(5) C8 0.0256(6) 0.0238(6) 0.0141(5) -0.0002(4) 0.0091(5) 0.0027(5) C9 0.0168(5) 0.0170(5) 0.0128(5) 0.0022(4) 0.0056(4) 0.0022(4) C10 0.0147(5) 0.0208(5) 0.0170(5) 0.0057(4) 0.0059(4) 0.0038(4) C11 0.0163(6) 0.0378(8) 0.0309(7) 0.0056(6) 0.0064(5) -0.0025(5) C12 0.0311(7) 0.0261(6) 0.0282(7) 0.0114(5) 0.0149(6) 0.0131(5) C13 0.0157(5) 0.0262(6) 0.0158(5) 0.0029(4) 0.0061(4) 0.0037(4) C14 0.0257(7) 0.0314(8) 0.0541(10) 0.0078(7) 0.0112(7) 0.0115(6) C15 0.0203(6) 0.0356(8) 0.0300(7) 0.0081(6) 0.0063(5) -0.0031(5) C16 0.0139(5) 0.0127(4) 0.0078(4) -0.0009(4) 0.0019(4) -0.0004(4) C17 0.0136(5) 0.0166(5) 0.0119(5) -0.0028(4) 0.0029(4) -0.0006(4) C18 0.0151(5) 0.0196(5) 0.0141(5) -0.0010(4) -0.0002(4) 0.0011(4) C19 0.0217(6) 0.0178(5) 0.0120(5) 0.0014(4) 0.0012(4) 0.0009(4) C20 0.0201(5) 0.0178(5) 0.0116(5) 0.0014(4) 0.0057(4) -0.0009(4) C21 0.0146(5) 0.0122(5) 0.0107(5) -0.0010(4) 0.0037(4) -0.0007(4) C22 0.0136(5) 0.0274(6) 0.0147(5) -0.0032(4) 0.0047(4) -0.0021(4) C23 0.0196(6) 0.0326(7) 0.0359(8) -0.0080(6) 0.0130(6) -0.0001(5) C24 0.0250(6) 0.0264(6) 0.0222(6) -0.0019(5) 0.0100(5) -0.0070(5) C25 0.0136(5) 0.0172(5) 0.0134(5) 0.0003(4) 0.0047(4) -0.0003(4) C26 0.0218(6) 0.0227(6) 0.0259(6) -0.0004(5) 0.0081(5) -0.0074(5) C27 0.0201(6) 0.0288(6) 0.0208(6) -0.0041(5) 0.0081(5) 0.0040(5) C28 0.0136(5) 0.0120(4) 0.0090(4) -0.0005(4) 0.0043(4) -0.0005(4) C29 0.0126(5) 0.0142(5) 0.0128(5) -0.0010(4) 0.0033(4) -0.0007(4) C30 0.0136(5) 0.0143(5) 0.0133(5) 0.0005(4) 0.0038(4) 0.0008(4) C31 0.0144(5) 0.0127(5) 0.0111(5) -0.0012(4) 0.0059(4) -0.0010(4) C32 0.0135(5) 0.0154(5) 0.0144(5) -0.0006(4) 0.0026(4) -0.0018(4) C33 0.0134(5) 0.0150(5) 0.0144(5) 0.0010(4) 0.0020(4) 0.0000(4) C34 0.0173(5) 0.0133(5) 0.0118(5) -0.0010(4) 0.0057(4) -0.0015(4) C35 0.0187(5) 0.0156(5) 0.0161(5) -0.0001(4) 0.0061(4) -0.0004(4) C36 0.0252(6) 0.0159(5) 0.0187(6) 0.0009(4) 0.0095(5) 0.0027(4) C37 0.0315(7) 0.0136(5) 0.0238(6) -0.0019(4) 0.0139(5) -0.0028(5) C38 0.0245(6) 0.0171(5) 0.0260(6) -0.0042(5) 0.0125(5) -0.0063(4) C39 0.0186(5) 0.0161(5) 0.0193(5) -0.0023(4) 0.0088(4) -0.0024(4) C40 0.0299(8) 0.0348(8) 0.0635(12) -0.0062(8) 0.0168(8) -0.0018(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' Br Br -0.2901 2.4595 '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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.0946 -3 -5 0 0.1018 0 -5 1 0.0997 0 1 5 0.1530 -2 -1 -5 0.2089 4 0 -5 0.1250 5 1 3 0.0954 -5 0 2 0.0731 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C40 O1 H1 109.5 C1 N1 C2 109.30(9) C1 N1 C4 126.01(9) C2 N1 C4 123.41(9) C1 N2 C3 109.14(9) C1 N2 C16 126.20(9) C3 N2 C16 124.66(9) N1 C1 C28 126.85(10) N2 C1 N1 107.19(9) N2 C1 C28 125.96(10) N1 C2 H2 126.4 C3 C2 N1 107.11(10) C3 C2 H2 126.4 N2 C3 H3 126.4 C2 C3 N2 107.25(10) C2 C3 H3 126.4 C5 C4 N1 119.45(10) C9 C4 N1 116.90(10) C9 C4 C5 123.59(10) C4 C5 C10 122.96(10) C6 C5 C4 116.91(11) C6 C5 C10 120.04(11) C5 C6 H6 119.4 C7 C6 C5 121.16(11) C7 C6 H6 119.4 C6 C7 H7 119.9 C8 C7 C6 120.13(11) C8 C7 H7 119.9 C7 C8 H8 119.3 C7 C8 C9 121.37(12) C9 C8 H8 119.3 C4 C9 C13 123.64(11) C8 C9 C4 116.81(11) C8 C9 C13 119.50(11) C5 C10 H10 108.2 C5 C10 C11 112.58(11) C5 C10 C12 109.74(10) C11 C10 H10 108.2 C12 C10 H10 108.2 C12 C10 C11 109.91(11) C10 C11 H11A 109.5 C10 C11 H11B 109.5 C10 C11 H11C 109.5 H11A C11 H11B 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 C10 C12 H12A 109.5 C10 C12 H12B 109.5 C10 C12 H12C 109.5 H12A C12 H12B 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C9 C13 H13 107.8 C9 C13 C14 111.68(12) C9 C13 C15 110.38(10) C14 C13 H13 107.8 C14 C13 C15 111.13(12) C15 C13 H13 107.8 C13 C14 H14A 109.5 C13 C14 H14B 109.5 C13 C14 H14C 109.5 H14A C14 H14B 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C13 C15 H15A 109.5 C13 C15 H15B 109.5 C13 C15 H15C 109.5 H15A C15 H15B 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C17 C16 N2 117.83(10) C21 C16 N2 118.56(10) C21 C16 C17 123.61(10) C16 C17 C22 123.94(10) C18 C17 C16 117.12(11) C18 C17 C22 118.88(10) C17 C18 H18 119.6 C19 C18 C17 120.88(11) C19 C18 H18 119.6 C18 C19 H19 119.8 C18 C19 C20 120.45(11) C20 C19 H19 119.8 C19 C20 H20 119.4 C19 C20 C21 121.28(11) C21 C20 H20 119.4 C16 C21 C25 124.68(10) C20 C21 C16 116.65(10) C20 C21 C25 118.67(10) C17 C22 H22 108.6 C17 C22 C23 112.15(11) C17 C22 C24 109.19(10) C23 C22 H22 108.6 C23 C22 C24 109.72(11) C24 C22 H22 108.6 C22 C23 H23A 109.5 C22 C23 H23B 109.5 C22 C23 H23C 109.5 H23A C23 H23B 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 C22 C24 H24A 109.5 C22 C24 H24B 109.5 C22 C24 H24C 109.5 H24A C24 H24B 109.5 H24A C24 H24C 109.5 H24B C24 H24C 109.5 C21 C25 H25 108.1 C21 C25 C26 110.88(10) C21 C25 C27 111.05(10) C26 C25 H25 108.1 C26 C25 C27 110.49(10) C27 C25 H25 108.1 C25 C26 H26A 109.5 C25 C26 H26B 109.5 C25 C26 H26C 109.5 H26A C26 H26B 109.5 H26A C26 H26C 109.5 H26B C26 H26C 109.5 C25 C27 H27A 109.5 C25 C27 H27B 109.5 C25 C27 H27C 109.5 H27A C27 H27B 109.5 H27A C27 H27C 109.5 H27B C27 H27C 109.5 C29 C28 C1 120.54(10) C33 C28 C1 120.45(10) C33 C28 C29 119.00(10) C28 C29 H29 119.8 C30 C29 C28 120.42(10) C30 C29 H29 119.8 C29 C30 H30 119.5 C29 C30 C31 121.01(10) C31 C30 H30 119.5 C30 C31 C32 118.12(10) C30 C31 C34 121.03(10) C32 C31 C34 120.84(10) C31 C32 H32 119.5 C33 C32 C31 121.03(10) C33 C32 H32 119.5 C28 C33 H33 119.8 C32 C33 C28 120.42(10) C32 C33 H33 119.8 C35 C34 C31 120.62(10) C35 C34 C39 118.61(11) C39 C34 C31 120.76(10) C34 C35 H35 119.8 C36 C35 C34 120.38(11) C36 C35 H35 119.8 C35 C36 H36 119.8 C37 C36 C35 120.43(12) C37 C36 H36 119.8 C36 C37 H37 120.3 C36 C37 C38 119.49(12) C38 C37 H37 120.3 C37 C38 H38 119.7 C39 C38 C37 120.65(12) C39 C38 H38 119.7 C34 C39 H39 119.8 C38 C39 C34 120.42(12) C38 C39 H39 119.8 O1 C40 H40A 109.5 O1 C40 H40B 109.5 O1 C40 H40C 109.5 H40A C40 H40B 109.5 H40A C40 H40C 109.5 H40B C40 H40C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 H1 0.8400 O1 C40 1.413(2) N1 C1 1.3517(14) N1 C2 1.3851(14) N1 C4 1.4542(14) N2 C1 1.3492(14) N2 C3 1.3883(14) N2 C16 1.4554(14) C1 C28 1.4645(15) C2 H2 0.9500 C2 C3 1.3545(16) C3 H3 0.9500 C4 C5 1.4006(16) C4 C9 1.3999(16) C5 C6 1.3979(16) C5 C10 1.5172(17) C6 H6 0.9500 C6 C7 1.3875(19) C7 H7 0.9500 C7 C8 1.3853(19) C8 H8 0.9500 C8 C9 1.3967(17) C9 C13 1.5179(17) C10 H10 1.0000 C10 C11 1.5349(19) C10 C12 1.5334(18) C11 H11A 0.9800 C11 H11B 0.9800 C11 H11C 0.9800 C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 H13 1.0000 C13 C14 1.525(2) C13 C15 1.5336(19) C14 H14A 0.9800 C14 H14B 0.9800 C14 H14C 0.9800 C15 H15A 0.9800 C15 H15B 0.9800 C15 H15C 0.9800 C16 C17 1.4021(15) C16 C21 1.4010(16) C17 C18 1.3964(16) C17 C22 1.5211(17) C18 H18 0.9500 C18 C19 1.3854(18) C19 H19 0.9500 C19 C20 1.3871(17) C20 H20 0.9500 C20 C21 1.3979(15) C21 C25 1.5196(16) C22 H22 1.0000 C22 C23 1.5360(19) C22 C24 1.5364(18) C23 H23A 0.9800 C23 H23B 0.9800 C23 H23C 0.9800 C24 H24A 0.9800 C24 H24B 0.9800 C24 H24C 0.9800 C25 H25 1.0000 C25 C26 1.5313(17) C25 C27 1.5350(17) C26 H26A 0.9800 C26 H26B 0.9800 C26 H26C 0.9800 C27 H27A 0.9800 C27 H27B 0.9800 C27 H27C 0.9800 C28 C29 1.3984(15) C28 C33 1.3982(15) C29 H29 0.9500 C29 C30 1.3895(15) C30 H30 0.9500 C30 C31 1.4023(15) C31 C32 1.4024(15) C31 C34 1.4859(15) C32 H32 0.9500 C32 C33 1.3893(16) C33 H33 0.9500 C34 C35 1.4020(16) C34 C39 1.4028(16) C35 H35 0.9500 C35 C36 1.3941(16) C36 H36 0.9500 C36 C37 1.3873(19) C37 H37 0.9500 C37 C38 1.3887(19) C38 H38 0.9500 C38 C39 1.3875(17) C39 H39 0.9500 C40 H40A 0.9800 C40 H40B 0.9800 C40 H40C 0.9800 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 N1 C1 C28 C29 -134.54(12) N1 C1 C28 C33 46.49(17) N1 C2 C3 N2 -0.18(13) N1 C4 C5 C6 -178.13(10) N1 C4 C5 C10 -1.46(16) N1 C4 C9 C8 179.01(10) N1 C4 C9 C13 1.38(16) N2 C1 C28 C29 44.96(16) N2 C1 C28 C33 -134.02(12) N2 C16 C17 C18 -179.87(10) N2 C16 C17 C22 -2.55(16) N2 C16 C21 C20 179.88(10) N2 C16 C21 C25 0.24(16) C1 N1 C2 C3 0.87(13) C1 N1 C4 C5 -100.70(13) C1 N1 C4 C9 82.04(14) C1 N2 C3 C2 -0.58(13) C1 N2 C16 C17 -104.63(13) C1 N2 C16 C21 76.31(14) C1 C28 C29 C30 -178.54(10) C1 C28 C33 C32 178.23(11) C2 N1 C1 N2 -1.23(12) C2 N1 C1 C28 178.35(11) C2 N1 C4 C5 93.61(13) C2 N1 C4 C9 -83.65(14) C3 N2 C1 N1 1.11(12) C3 N2 C1 C28 -178.47(10) C3 N2 C16 C17 76.16(14) C3 N2 C16 C21 -102.90(13) C4 N1 C1 N2 -168.60(10) C4 N1 C1 C28 10.97(18) C4 N1 C2 C3 168.65(10) C4 C5 C6 C7 -0.18(18) C4 C5 C10 C11 138.52(12) C4 C5 C10 C12 -98.73(13) C4 C9 C13 C14 -122.36(14) C4 C9 C13 C15 113.48(13) C5 C4 C9 C8 1.88(17) C5 C4 C9 C13 -175.76(11) C5 C6 C7 C8 0.5(2) C6 C5 C10 C11 -44.91(15) C6 C5 C10 C12 77.84(14) C6 C7 C8 C9 0.3(2) C7 C8 C9 C4 -1.49(18) C7 C8 C9 C13 176.25(12) C8 C9 C13 C14 60.07(16) C8 C9 C13 C15 -64.09(15) C9 C4 C5 C6 -1.06(17) C9 C4 C5 C10 175.61(11) C10 C5 C6 C7 -176.95(11) C16 N2 C1 N1 -178.20(10) C16 N2 C1 C28 2.22(18) C16 N2 C3 C2 178.74(10) C16 C17 C18 C19 0.35(17) C16 C17 C22 C23 128.12(12) C16 C17 C22 C24 -110.05(13) C16 C21 C25 C26 -117.33(12) C16 C21 C25 C27 119.42(12) C17 C16 C21 C20 0.88(16) C17 C16 C21 C25 -178.77(10) C17 C18 C19 C20 0.07(19) C18 C17 C22 C23 -54.61(15) C18 C17 C22 C24 67.22(14) C18 C19 C20 C21 -0.04(18) C19 C20 C21 C16 -0.41(17) C19 C20 C21 C25 179.26(11) C20 C21 C25 C26 63.03(14) C20 C21 C25 C27 -60.22(14) C21 C16 C17 C18 -0.85(17) C21 C16 C17 C22 176.46(11) C22 C17 C18 C19 -177.10(11) C28 C29 C30 C31 0.18(17) C29 C28 C33 C32 -0.76(17) C29 C30 C31 C32 -0.49(17) C29 C30 C31 C34 -179.34(11) C30 C31 C32 C33 0.17(17) C30 C31 C34 C35 22.44(17) C30 C31 C34 C39 -158.07(11) C31 C32 C33 C28 0.45(18) C31 C34 C35 C36 178.39(11) C31 C34 C39 C38 -178.19(11) C32 C31 C34 C35 -156.38(11) C32 C31 C34 C39 23.11(17) C33 C28 C29 C30 0.45(17) C34 C31 C32 C33 179.02(11) C34 C35 C36 C37 -0.12(19) C35 C34 C39 C38 1.32(18) C35 C36 C37 C38 1.17(19) C36 C37 C38 C39 -1.0(2) C37 C38 C39 C34 -0.3(2) C39 C34 C35 C36 -1.11(17) loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.0003 0.9988 0.0000 -0.0013 -0.0333 0.0019 -2.9966 -4.9892 0.0022 0.1895 0.1644 0.0754 0.0017 -4.9936 0.9993 -0.0259 0.1698 0.0244 0.0000 1.0013 4.9971 -0.1622 -0.0176 0.1717 -1.9988 -0.9980 -4.9956 0.2844 0.0161 -0.1151 3.9973 -0.0090 -5.0002 -0.0834 -0.0126 -0.2831 4.9969 0.9921 2.9944 -0.4033 -0.0201 -0.0378 -4.9969 0.0092 2.0027 0.2411 0.0025 0.2095