#------------------------------------------------------------------------------ #$Date: 2021-10-01 03:34:17 +0300 (Fri, 01 Oct 2021) $ #$Revision: 269416 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060985.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_7060985 loop_ _publ_author_name 'Zhang, Yin-Qiang' 'Xu, Guan-Cheng' 'Luo, Yan' _publ_section_title ; (C2H5NH3)3[InBr6]: an indium(III) organic-inorganic hybrid phase transition compound exhibiting switchable dielectric response ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ03814A _journal_year 2021 _chemical_formula_moiety 'Br6 In, 1.5(C4 H16 N2)' _chemical_formula_sum 'C6 H24 Br6 In N3' _chemical_formula_weight 732.56 _space_group_crystal_system monoclinic _space_group_IT_number 12 _space_group_name_Hall '-C 2y' _space_group_name_H-M_alt 'C 1 2/m 1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2021-09-17 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-09-17 deposited with the CCDC. 2021-09-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 105.770(15) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 22.548(10) _cell_length_b 8.033(4) _cell_length_c 11.737(5) _cell_measurement_reflns_used 2350 _cell_measurement_temperature 293 _cell_measurement_theta_max 25.95 _cell_measurement_theta_min 2.70 _cell_volume 2045.9(16) _computing_cell_refinement 'SAINT V8.40A (?, 2016)' _computing_data_collection Bruker _computing_data_reduction 'SAINT V8.40A (?, 2016)' _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 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 293.0 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _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 0.0645 _diffrn_reflns_av_unetI/netI 0.0599 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 7959 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.507 _diffrn_reflns_theta_min 1.877 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 12.860 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.2563 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1578 before and 0.0698 after correction. The Ratio of minimum to maximum transmission is 0.3437. The \l/2 correction factor is Not present. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 2.378 _exptl_crystal_description block _exptl_crystal_F_000 1360 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 1.300 _refine_diff_density_min -1.048 _refine_diff_density_rms 0.155 _refine_ls_extinction_coef 0.00268(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 96 _refine_ls_number_reflns 2053 _refine_ls_number_restraints 28 _refine_ls_restrained_S_all 1.066 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0507 _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^)+(0.0476P)^2^+24.1980P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1313 _refine_ls_wR_factor_ref 0.1444 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1437 _reflns_number_total 2053 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj03814a2.cif _cod_data_source_block 293K _cod_original_cell_volume 2045.8(15) _cod_database_code 7060985 _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 0.360 _shelx_estimated_absorpt_t_min 0.308 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H,H) groups, All N(H,H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C4-C5 1.5 with sigma of 0.002 C5-N1 1.45 with sigma of 0.002 C6-C1 1.5 with sigma of 0.002 C2-C3 1.5 with sigma of 0.002 3. Uiso/Uaniso restraints and constraints N1 \\sim C5 \\sim C4: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004 N3 \\sim C6 \\sim C1: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004 4. Others Fixed Sof: H2A(0.5) H2B(0.5) H2C(0.5) H3C(0.5) H3D(0.5) H3E(0.5) H2D(0.5) H2E(0.5) H2F(0.5) H1D(0.5) H1E(0.5) H1F(0.5) H3A(0.5) H3B(0.5) H6A(0.5) H6B(0.5) C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) H5A(0.5) H5B(0.5) H4A(0.5) H4B(0.5) H4C(0.5) 5.a Riding coordinates: N2(H2A,H2B,H2C), N3(H3C,H3D,H3E), N1(H1D,H1E,H1F), C6(H6A,H6B), C1(H1A,H1B, H1C), C4(H4A,H4B,H4C) 5.b Secondary CH2 refined with riding coordinates: C3(H3A,H3B), C5(H5A,H5B) 5.c Idealised Me refined as rotating group: C2(H2D,H2E,H2F) ; _shelx_res_file ; a.res created by SHELXL-2014/7 TITL a_a.res in C2/m REM Old TITL A in C2/m REM SHELXT solution in C2/m: R1 0.206, Rweak 0.011, Alpha 0.031 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C6 N3 Br6 In CELL 0.71073 22.5481 8.0326 11.7372 90 105.77 90 ZERR 4 0.0097 0.0039 0.0045 0 0.015 0 LATT 7 SYMM -X,+Y,-Z SFAC C H Br In N UNIT 24 96 24 4 12 EQIV $1 +X,1-Y,+Z DFIX 1.5 0.002 C4 C5 DFIX 1.45 0.002 C5 N1 DFIX 1.5 0.002 C6 C1 DFIX 1.5 0.002 C2 C3 SIMU 0.002 0.004 2 N1 C5 C4 SIMU 0.002 0.004 2 N3 C6 C1 L.S. 80 0 23 PLAN 8 SIZE 0.1 0.12 0.1 TEMP 19.85 BIND C1 C6 FREE C1 C1_$1 FREE C1 C6_$1 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta OMIT -3 51.02 REM REM REM WGHT 0.047600 24.198000 EXTI 0.002679 FVAR 0.17645 IN1 4 0.667005 0.500000 0.712565 10.50000 0.04969 0.04820 = 0.04390 0.00000 0.01010 0.00000 BR1 3 0.751638 0.737436 0.774179 11.00000 0.05916 0.05571 = 0.07282 -0.00455 0.00631 -0.00949 BR3 3 0.579504 0.264142 0.635630 11.00000 0.05209 0.05758 = 0.09231 -0.01121 0.02019 -0.00755 BR4 3 0.682150 0.500000 0.491011 10.50000 0.04359 0.15476 = 0.04371 0.00000 0.01268 0.00000 BR2 3 0.647577 0.500000 0.923724 10.50000 0.09836 0.11006 = 0.05169 0.00000 0.03303 0.00000 N2 5 0.673115 1.000000 0.532059 10.50000 0.04938 0.09325 = 0.05921 0.00000 0.02043 0.00000 PART -1 AFIX 3 H2A 2 0.672895 0.896630 0.559249 10.50000 -1.20000 H2B 2 0.649835 1.064750 0.563889 10.50000 -1.20000 H2C 2 0.711555 1.038620 0.551449 10.50000 -1.20000 AFIX 0 PART 0 N3 5 0.537037 0.500000 0.342483 10.50000 0.07467 0.17241 = 0.08614 0.00000 0.02289 0.00000 PART -1 AFIX 3 H3C 2 0.518797 0.407970 0.358353 10.50000 -1.20000 H3D 2 0.516747 0.588820 0.357293 10.50000 -1.20000 H3E 2 0.575737 0.503210 0.387713 10.50000 -1.20000 AFIX 0 PART 0 C2 1 0.580962 1.000000 0.360044 10.50000 0.12655 0.09719 = 0.09067 0.00000 -0.00344 0.00000 PART -1 AFIX 137 H2D 2 0.569341 1.043899 0.280999 10.50000 -1.50000 H2E 2 0.563595 1.067922 0.410121 10.50000 -1.50000 H2F 2 0.565850 0.888179 0.359431 10.50000 -1.50000 AFIX 0 PART 0 N1 5 0.806006 0.500000 1.045621 10.50000 0.12114 0.18347 = 0.10698 0.00000 0.03698 0.00000 PART -1 AFIX 3 H1D 2 0.792935 0.599940 1.016721 10.50000 -1.20000 H1E 2 0.790416 0.476360 1.105731 10.50000 -1.20000 H1F 2 0.793716 0.423700 0.989151 10.50000 -1.20000 AFIX 0 PART 0 C3 1 0.649841 1.000000 0.406246 10.50000 0.06793 0.16718 = 0.09706 0.00000 0.02687 0.00000 AFIX 23 H3A 2 0.665727 0.902628 0.375467 10.50000 -1.20000 H3B 2 0.665727 1.097372 0.375467 10.50000 -1.20000 AFIX 0 C6 1 0.532912 0.500000 0.221122 10.50000 0.07716 0.17382 = 0.08836 0.00000 0.02147 0.00000 AFIX 3 H6A 2 0.545282 0.389150 0.204112 10.50000 -1.20000 H6B 2 0.490332 0.518910 0.177322 10.50000 -1.20000 AFIX 0 C1 1 0.568413 0.612811 0.161922 10.50000 0.08179 0.17411 = 0.09092 -0.00032 0.01941 0.00000 AFIX 3 H1A 2 0.555013 0.609171 0.077002 10.50000 -1.50000 H1B 2 0.563303 0.723611 0.188422 10.50000 -1.50000 H1C 2 0.611053 0.581781 0.188422 10.50000 -1.50000 AFIX 0 C5 1 0.872691 0.500000 1.086918 10.50000 0.12411 0.18382 = 0.11308 0.00000 0.03364 0.00000 AFIX 23 H5A 2 0.884469 0.403109 1.137326 10.50000 -1.20000 H5B 2 0.884469 0.596891 1.137326 10.50000 -1.20000 AFIX 0 C4 1 0.911919 0.500000 1.002266 10.50000 0.12437 0.18425 = 0.11505 0.00000 0.03394 0.00000 PART -1 AFIX 3 H4A 2 0.952509 0.464140 1.044816 10.50000 -1.50000 H4B 2 0.913989 0.610440 0.972326 10.50000 -1.50000 H4C 2 0.895499 0.425420 0.937456 10.50000 -1.50000 AFIX 0 HKLF 4 REM a_a.res in C2/m REM R1 = 0.0507 for 1437 Fo > 4sig(Fo) and 0.0745 for all 2053 data REM 96 parameters refined using 28 restraints END WGHT 0.0476 24.2037 REM Highest difference peak 1.300, deepest hole -1.048, 1-sigma level 0.155 Q1 1 0.5957 0.2433 0.7144 11.00000 0.05 1.05 Q2 1 0.5400 1.0000 0.4013 10.50000 0.05 0.75 Q3 1 0.7502 0.7201 0.7013 11.00000 0.05 0.67 Q4 1 0.4830 1.0000 0.3901 10.50000 0.05 0.65 Q5 1 0.6165 0.5471 0.8734 11.00000 0.05 0.64 Q6 1 0.5391 0.4020 0.1598 11.00000 0.05 0.59 Q7 1 0.7864 0.7202 0.8221 11.00000 0.05 0.58 Q8 1 0.7033 0.5000 0.9536 10.50000 0.05 0.56 ; _shelx_res_checksum 47551 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, 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 In1 In 0.66701(3) 0.5000 0.71257(5) 0.04777(17) Uani 1 2 d S T P . . Br1 Br 0.75164(4) 0.73744(9) 0.77418(7) 0.0648(2) Uani 1 1 d . . . . . Br3 Br 0.57950(3) 0.26414(9) 0.63563(7) 0.0672(2) Uani 1 1 d . . . . . Br4 Br 0.68215(5) 0.5000 0.49101(8) 0.0805(4) Uani 1 2 d S T P . . Br2 Br 0.64758(6) 0.5000 0.92372(9) 0.0842(4) Uani 1 2 d S T P . . N2 N 0.6731(4) 1.0000 0.5321(6) 0.066(3) Uani 1 2 d S T P . . H2A H 0.6729 0.8966 0.5592 0.079 Uiso 0.5 1 d R . . A -1 H2B H 0.6498 1.0647 0.5639 0.079 Uiso 0.5 1 d R . . A -1 H2C H 0.7116 1.0386 0.5514 0.079 Uiso 0.5 1 d R . . A -1 N3 N 0.5370(5) 0.5000 0.3425(9) 0.1109(10) Uani 1 2 d S TU P . . H3C H 0.5188 0.4080 0.3584 0.133 Uiso 0.5 1 d R . . B -1 H3D H 0.5167 0.5888 0.3573 0.133 Uiso 0.5 1 d R . . B -1 H3E H 0.5757 0.5032 0.3877 0.133 Uiso 0.5 1 d R . . B -1 C2 C 0.58096(8) 1.0000 0.3600(10) 0.111(6) Uani 1 2 d DS T P . . H2D H 0.5693 1.0439 0.2810 0.167 Uiso 0.5 1 calc GR . . C -1 H2E H 0.5636 1.0679 0.4101 0.167 Uiso 0.5 1 calc GR . . C -1 H2F H 0.5659 0.8882 0.3594 0.167 Uiso 0.5 1 calc GR . . C -1 N1 N 0.80601(8) 0.5000 1.0456(10) 0.1360(19) Uani 1 2 d DS TU P . . H1D H 0.7929 0.5999 1.0167 0.163 Uiso 0.5 1 d R . . D -1 H1E H 0.7904 0.4764 1.1057 0.163 Uiso 0.5 1 d R . . D -1 H1F H 0.7937 0.4237 0.9892 0.163 Uiso 0.5 1 d R . . D -1 C3 C 0.64984(8) 1.0000 0.4062(10) 0.110(6) Uani 1 2 d DS T P . . H3A H 0.6657 0.9026 0.3755 0.132 Uiso 0.5 1 calc R . . . . H3B H 0.6657 1.0974 0.3755 0.132 Uiso 0.5 1 calc R . . . . C6 C 0.53291(12) 0.5000 0.2211(3) 0.1133(9) Uani 1 2 d DS TU P . . H6A H 0.5453 0.3892 0.2041 0.136 Uiso 0.5 1 d R . . . . H6B H 0.4903 0.5189 0.1773 0.136 Uiso 0.5 1 d R . . . . C1 C 0.56841(12) 0.6128(4) 0.1619(3) 0.1164(18) Uani 0.5 1 d D U . . . H1A H 0.5550 0.6092 0.0770 0.175 Uiso 0.5 1 d R . . . . H1B H 0.5633 0.7236 0.1884 0.175 Uiso 0.5 1 d R . . . . H1C H 0.6111 0.5818 0.1884 0.175 Uiso 0.5 1 d R . . . . C5 C 0.87269(6) 0.5000 1.08692(18) 0.1401(15) Uani 1 2 d DS TU P . . H5A H 0.8845 0.4031 1.1373 0.168 Uiso 0.5 1 calc R . . . . H5B H 0.8845 0.5969 1.1373 0.168 Uiso 0.5 1 calc R . . . . C4 C 0.91192(10) 0.5000 1.00227(19) 0.1410(19) Uani 1 2 d DS TU P . . H4A H 0.9525 0.4641 1.0448 0.211 Uiso 0.5 1 d R . . E -1 H4B H 0.9140 0.6104 0.9723 0.211 Uiso 0.5 1 d R . . E -1 H4C H 0.8955 0.4254 0.9375 0.211 Uiso 0.5 1 d R . . E -1 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 In1 0.0497(3) 0.0482(3) 0.0439(3) 0.000 0.0101(2) 0.000 Br1 0.0592(4) 0.0557(4) 0.0728(4) -0.0046(3) 0.0063(3) -0.0095(3) Br3 0.0521(4) 0.0576(4) 0.0923(5) -0.0112(4) 0.0202(3) -0.0075(3) Br4 0.0436(5) 0.1548(12) 0.0437(4) 0.000 0.0127(4) 0.000 Br2 0.0984(8) 0.1101(10) 0.0517(5) 0.000 0.0330(5) 0.000 N2 0.049(4) 0.093(6) 0.059(4) 0.000 0.020(3) 0.000 N3 0.0747(16) 0.1724(16) 0.0861(16) 0.000 0.0229(16) 0.000 C2 0.127(12) 0.097(10) 0.091(9) 0.000 -0.003(9) 0.000 N1 0.121(3) 0.183(3) 0.107(3) 0.000 0.037(3) 0.000 C3 0.068(8) 0.167(15) 0.097(9) 0.000 0.027(6) 0.000 C6 0.0772(15) 0.1738(15) 0.0884(15) 0.000 0.0215(14) 0.000 C1 0.082(3) 0.174(3) 0.091(3) 0.000(3) 0.019(3) 0.000(3) C5 0.124(2) 0.184(2) 0.113(2) 0.000 0.034(2) 0.000 C4 0.124(3) 0.184(3) 0.115(3) 0.000 0.034(3) 0.000 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' In In -0.7276 1.3100 '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' 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 Br1 In1 Br1 91.81(5) . 6_565 ? Br1 In1 Br3 89.59(4) 6_565 . ? Br1 In1 Br3 89.59(4) . 6_565 ? Br1 In1 Br3 176.44(3) . . ? Br1 In1 Br3 176.44(3) 6_565 6_565 ? Br1 In1 Br4 89.58(3) . . ? Br1 In1 Br4 89.58(3) 6_565 . ? Br3 In1 Br3 88.82(5) . 6_565 ? Br3 In1 Br4 87.16(3) . . ? Br3 In1 Br4 87.16(3) 6_565 . ? Br2 In1 Br1 91.99(3) . . ? Br2 In1 Br1 91.99(3) . 6_565 ? Br2 In1 Br3 91.22(4) . 6_565 ? Br2 In1 Br3 91.22(4) . . ? Br2 In1 Br4 177.74(5) . . ? H2A N2 H2B 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C3 N2 H2A 109.6 . . ? C3 N2 H2B 110.0 . . ? C3 N2 H2C 108.9 . . ? H3C N3 H3D 109.5 . . ? H3C N3 H3E 109.5 . . ? H3D N3 H3E 109.5 . . ? C6 N3 H3C 107.8 . . ? C6 N3 H3C 107.8 6_565 . ? C6 N3 H3D 107.6 6_565 . ? C6 N3 H3D 107.6 . . ? C6 N3 H3E 112.9 . . ? C6 N3 H3E 112.9 6_565 . ? C6 N3 C6 0.0 6_565 . ? H2D C2 H2E 109.5 . . ? H2D C2 H2F 109.5 . . ? H2E C2 H2F 109.5 . . ? C3 C2 H2D 109.5 . . ? C3 C2 H2E 109.5 . . ? C3 C2 H2F 109.5 . . ? H1D N1 H1E 109.5 . . ? H1D N1 H1F 109.5 . . ? H1E N1 H1F 109.5 . . ? C5 N1 H1D 109.5 . . ? C5 N1 H1E 109.4 . . ? C5 N1 H1F 109.5 . . ? N2 C3 C2 115.3(8) . . ? N2 C3 H3A 108.4 . . ? N2 C3 H3B 108.4 . . ? C2 C3 H3A 108.4 . . ? C2 C3 H3B 108.4 . . ? H3A C3 H3B 107.5 . . ? N3 C6 H6A 105.4 . . ? N3 C6 H6B 108.7 . . ? N3 C6 C1 125.1(4) . 6_565 ? N3 C6 C1 125.1(4) . . ? C6 C6 N3 0(10) 6_565 . ? C6 C6 H6A 0.0 6_565 . ? C6 C6 H6B 0.0 6_565 . ? C6 C6 C1 0(10) 6_565 . ? C6 C6 C1 0(10) 6_565 6_565 ? H6A C6 H6B 109.5 . . ? C1 C6 H6A 29.5 6_565 . ? C1 C6 H6A 103.9 . . ? C1 C6 H6B 103.7 . . ? C1 C6 H6B 115.2 6_565 . ? C1 C6 C1 74.4(3) . 6_565 ? C6 C1 H1A 113.9 . . ? C6 C1 H1B 106.5 . . ? C6 C1 H1C 107.9 . . ? H1A C1 H1B 109.4 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C5 H5A 106.9 . . ? N1 C5 H5B 106.9 . . ? N1 C5 C4 121.6(5) . . ? H5A C5 H5B 106.7 . . ? C4 C5 H5A 106.9 . . ? C4 C5 H5B 106.9 . . ? C5 C4 H4A 107.8 . . ? C5 C4 H4B 109.8 . . ? C5 C4 H4C 110.8 . . ? H4A C4 H4B 109.5 . . ? H4A C4 H4C 109.4 . . ? H4B C4 H4C 109.5 . . ? 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 In1 Br1 2.6556(12) . ? In1 Br1 2.6556(12) 6_565 ? In1 Br3 2.7072(12) . ? In1 Br3 2.7073(12) 6_565 ? In1 Br4 2.7132(16) . ? In1 Br2 2.6315(16) . ? N2 H2A 0.8900 . ? N2 H2B 0.8901 . ? N2 H2C 0.8900 . ? N2 C3 1.426(13) . ? N3 H3C 0.8899 . ? N3 H3D 0.8898 . ? N3 H3E 0.8900 . ? N3 C6 1.402(11) . ? N3 C6 1.402(11) 6_565 ? C2 H2D 0.9600 . ? C2 H2E 0.9600 . ? C2 H2F 0.9600 . ? C2 C3 1.4995(19) . ? N1 H1D 0.8900 . ? N1 H1E 0.8901 . ? N1 H1F 0.8899 . ? N1 C5 1.4490(18) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C6 C6 0.000000(3) 6_565 ? C6 H6A 0.9699 . ? C6 H6B 0.9700 . ? C6 C1 1.4990(19) 6_565 ? C6 C1 1.4990(19) . ? C1 H1A 0.9602 . ? C1 H1B 0.9600 . ? C1 H1C 0.9595 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 C4 1.4991(19) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? 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 C6 N3 C6 C1 0(100) 6_565 . . . ? C6 N3 C6 C1 0(100) 6_565 . . 6_565 ?