#------------------------------------------------------------------------------ #$Date: 2024-01-06 11:55:43 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288908 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247675.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_7247675 loop_ _publ_author_name 'Bhattacharyya, Arghyadeep' 'Das, Akash' 'Guchhait, Nikhil' _publ_section_title ; Interrogating the nature of aggregates formed in a model azine based ESIPT coupled AIE active probe: stark differences in photodynamics in the solid state and aggregates in water. ; _journal_issue 46 _journal_name_full 'Physical chemistry chemical physics : PCCP' _journal_page_first 31702 _journal_page_last 31713 _journal_paper_doi 10.1039/d3cp03603k _journal_volume 25 _journal_year 2023 _chemical_formula_moiety C19H15BrN2O _chemical_formula_sum 'C19 H15 Br N2 O' _chemical_formula_weight 367.2443 _chemical_melting_point 503 _chemical_name_common BNHMP _chemical_name_systematic 4-bromo-2-((E)-((Z)-(1-(naphthalen-2-yl)ethylidene)hydrazono)methyl)phenol _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 _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2023-08-28 deposited with the CCDC. 2023-10-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.681(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.2672(6) _cell_length_b 14.7584(12) _cell_length_c 17.2093(13) _cell_measurement_reflns_used 2884 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 22.13 _cell_measurement_theta_min 3.58 _cell_volume 1586.4(2) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _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 0.0471 _diffrn_reflns_av_unetI/netI 0.0265 _diffrn_reflns_Laue_measured_fraction_full 0.984 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 13985 _diffrn_reflns_point_group_measured_fraction_full 0.984 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_theta_full 20.456 _diffrn_reflns_theta_max 20.456 _diffrn_reflns_theta_min 2.747 _exptl_absorpt_coefficient_mu 2.597 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details SADABS _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.538 _exptl_crystal_description rhombic _exptl_crystal_F_000 1140 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.17 _exptl_transmission_factor_max 2.013 _exptl_transmission_factor_min 1.257 _refine_diff_density_max 0.156 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.036 _refine_ls_extinction_coef 0.0004(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)' _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 1556 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0278 _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^)+(0.0390P)^2^+0.8088P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0727 _refine_ls_wR_factor_ref 0.0758 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1339 _reflns_number_total 1556 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3cp03603k2.cif _cod_data_source_block BNHMP _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'EMPIRICAL' was changed to 'empirical' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas Adding full bibliography for 7247675.cif. ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7247675 _shelx_shelxl_version_number 2016/6 _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_min 0.746 _shelx_estimated_absorpt_t_max 0.572 _shelx_res_file ; TITL DD_2022_82_0m_a.res in P2(1)/n DD_2022_82_0m_a.res created by SHELXL-2016/6 at 12:03:30 on 28-Aug-2023 CELL 0.71073 6.2672 14.7584 17.2093 90 94.681 90 ZERR 20 0.0006 0.0012 0.0013 0 0.004 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Br N O UNIT 20 20 20 20 20 L.S. 10 ACTA BOND $H FMAP 2 PLAN 5 MORE -1 CONF TEMP 23 WGHT 0.039000 0.808800 EXTI 0.000407 FVAR 0.39691 BR1 3 0.843178 0.401426 0.941115 11.00000 0.07137 0.12325 = 0.05136 0.00028 -0.00046 0.00582 O1 5 0.182100 0.459918 0.673643 11.00000 0.05106 0.08170 = 0.06274 -0.00310 0.00289 0.01516 AFIX 147 H1 2 0.230226 0.449293 0.631688 11.00000 -1.50000 AFIX 0 N2 4 0.527541 0.372348 0.509889 11.00000 0.05118 0.05292 = 0.04627 -0.00029 0.00777 0.00381 N1 4 0.455401 0.398984 0.581411 11.00000 0.04836 0.05586 = 0.04648 0.00250 0.00674 0.00246 C6 1 0.538609 0.410675 0.718239 11.00000 0.04078 0.03802 = 0.05005 -0.00084 0.00997 -0.00183 C8 1 0.384580 0.380486 0.452714 11.00000 0.04519 0.04312 = 0.04863 0.00243 0.00604 0.00016 C10 1 0.444094 0.352601 0.375062 11.00000 0.04191 0.03732 = 0.05359 0.00319 0.00656 -0.00044 C17 1 0.369243 0.340291 0.233950 11.00000 0.05139 0.03690 = 0.04566 -0.00287 0.00311 -0.00106 C18 1 0.572002 0.301240 0.227374 11.00000 0.04962 0.03726 = 0.05353 -0.00372 0.00883 0.00000 C5 1 0.686535 0.396759 0.781935 11.00000 0.03955 0.04626 = 0.05733 -0.00041 0.00553 -0.00098 AFIX 43 H4 2 0.820954 0.373416 0.774127 11.00000 -1.20000 AFIX 0 C1 1 0.334978 0.445152 0.731817 11.00000 0.04672 0.04551 = 0.05374 0.00058 0.00624 -0.00034 C7 1 0.592309 0.389145 0.639900 11.00000 0.04338 0.04319 = 0.05655 0.00125 0.01091 -0.00028 AFIX 43 H5 2 0.728628 0.367840 0.632185 11.00000 -1.20000 AFIX 0 C00D 1 0.311478 0.365408 0.308323 11.00000 0.04028 0.04295 = 0.05696 0.00178 0.00311 0.00396 AFIX 43 H7 2 0.178086 0.391754 0.312473 11.00000 -1.20000 AFIX 0 C11 1 0.645476 0.311187 0.367100 11.00000 0.04654 0.05598 = 0.05541 -0.00006 -0.00016 0.00653 AFIX 43 H13 2 0.737467 0.300368 0.411301 11.00000 -1.20000 AFIX 0 C2 1 0.289360 0.464468 0.807166 11.00000 0.04554 0.05547 = 0.06714 -0.00760 0.01378 0.00236 AFIX 43 H2 2 0.155370 0.487327 0.816255 11.00000 -1.20000 AFIX 0 C12 1 0.705744 0.287219 0.296356 11.00000 0.04390 0.05444 = 0.06968 -0.00371 0.00857 0.00973 AFIX 43 H12 2 0.839292 0.260699 0.293007 11.00000 -1.20000 AFIX 0 C16 1 0.227912 0.353655 0.163995 11.00000 0.06243 0.04369 = 0.06417 -0.00343 0.01307 0.00681 AFIX 43 H8 2 0.092589 0.378500 0.167318 11.00000 -1.20000 AFIX 0 C3 1 0.437875 0.450543 0.868597 11.00000 0.06139 0.06010 = 0.05305 -0.01147 0.01748 -0.00588 AFIX 43 H3 2 0.404683 0.463741 0.919060 11.00000 -1.20000 AFIX 0 C4 1 0.636777 0.416934 0.855660 11.00000 0.05109 0.05763 = 0.04469 -0.00308 0.00620 -0.00224 C13 1 0.630602 0.278683 0.152390 11.00000 0.06585 0.05184 = 0.07202 -0.00883 0.01716 0.00031 AFIX 43 H11 2 0.764473 0.253411 0.146898 11.00000 -1.20000 AFIX 0 C14 1 0.494965 0.293246 0.088238 11.00000 0.08982 0.06122 = 0.05388 -0.00959 0.01231 -0.00547 AFIX 43 H10 2 0.536635 0.278522 0.039155 11.00000 -1.20000 AFIX 0 C15 1 0.291557 0.330534 0.095714 11.00000 0.08819 0.05896 = 0.06059 -0.00219 -0.01127 -0.00117 AFIX 43 H9 2 0.199268 0.339133 0.051210 11.00000 -1.20000 AFIX 0 C9 1 0.166863 0.419123 0.461655 11.00000 0.05294 0.09483 = 0.06067 0.00134 0.01395 0.01131 AFIX 137 H6B 2 0.097093 0.384167 0.499229 11.00000 -1.50000 H6A 2 0.083336 0.417166 0.412377 11.00000 -1.50000 H6C 2 0.180664 0.480792 0.479090 11.00000 -1.50000 AFIX 0 HKLF 4 REM DD_2022_82_0m_a.res in P2(1)/n REM R1 = 0.0278 for 1339 Fo > 4sig(Fo) and 0.0342 for all 1556 data REM 211 parameters refined using 0 restraints END WGHT 0.0390 0.8083 REM Highest difference peak 0.156, deepest hole -0.169, 1-sigma level 0.036 Q1 1 0.1521 0.3809 0.1825 11.00000 0.05 0.16 Q2 1 0.7588 0.3516 0.9761 11.00000 0.05 0.15 Q3 1 0.8984 0.3556 0.9862 11.00000 0.05 0.14 Q4 1 0.3220 0.3650 0.1415 11.00000 0.05 0.14 Q5 1 0.1264 0.4698 0.4156 11.00000 0.05 0.13 ; _shelx_res_checksum 73727 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.84318(7) 0.40143(3) 0.94112(2) 0.0823(3) Uani 1 1 d . . . . . O1 O 0.1821(4) 0.45992(18) 0.67364(15) 0.0653(7) Uani 1 1 d . . . . . H1 H 0.230226 0.449293 0.631688 0.098 Uiso 1 1 calc R U . . . N2 N 0.5275(4) 0.37235(17) 0.50989(17) 0.0499(7) Uani 1 1 d . . . . . N1 N 0.4554(5) 0.39898(18) 0.58141(17) 0.0501(7) Uani 1 1 d . . . . . C6 C 0.5386(5) 0.4107(2) 0.7182(2) 0.0426(8) Uani 1 1 d . . . . . C8 C 0.3846(5) 0.3805(2) 0.4527(2) 0.0455(9) Uani 1 1 d . . . . . C10 C 0.4441(5) 0.3526(2) 0.37506(19) 0.0441(8) Uani 1 1 d . . . . . C17 C 0.3692(5) 0.3403(2) 0.23395(19) 0.0447(8) Uani 1 1 d . . . . . C18 C 0.5720(5) 0.3012(2) 0.2274(2) 0.0465(9) Uani 1 1 d . . . . . C5 C 0.6865(5) 0.3968(2) 0.7819(2) 0.0476(9) Uani 1 1 d . . . . . H4 H 0.820954 0.373416 0.774127 0.057 Uiso 1 1 calc R U . . . C1 C 0.3350(5) 0.4452(2) 0.7318(2) 0.0485(9) Uani 1 1 d . . . . . C7 C 0.5923(6) 0.3891(2) 0.6399(2) 0.0473(9) Uani 1 1 d . . . . . H5 H 0.728628 0.367840 0.632185 0.057 Uiso 1 1 calc R U . . . C00D C 0.3115(5) 0.3654(2) 0.3083(2) 0.0468(9) Uani 1 1 d . . . . . H7 H 0.178086 0.391754 0.312473 0.056 Uiso 1 1 calc R U . . . C11 C 0.6455(5) 0.3112(2) 0.3671(2) 0.0529(9) Uani 1 1 d . . . . . H13 H 0.737467 0.300368 0.411301 0.063 Uiso 1 1 calc R U . . . C2 C 0.2894(6) 0.4645(2) 0.8072(2) 0.0555(10) Uani 1 1 d . . . . . H2 H 0.155370 0.487327 0.816255 0.067 Uiso 1 1 calc R U . . . C12 C 0.7057(5) 0.2872(2) 0.2964(2) 0.0558(10) Uani 1 1 d . . . . . H12 H 0.839292 0.260699 0.293007 0.067 Uiso 1 1 calc R U . . . C16 C 0.2279(6) 0.3537(2) 0.1640(2) 0.0563(10) Uani 1 1 d . . . . . H8 H 0.092589 0.378500 0.167318 0.068 Uiso 1 1 calc R U . . . C3 C 0.4379(6) 0.4505(2) 0.8686(2) 0.0575(10) Uani 1 1 d . . . . . H3 H 0.404683 0.463741 0.919060 0.069 Uiso 1 1 calc R U . . . C4 C 0.6368(5) 0.4169(2) 0.8557(2) 0.0510(9) Uani 1 1 d . . . . . C13 C 0.6306(6) 0.2787(2) 0.1524(2) 0.0626(10) Uani 1 1 d . . . . . H11 H 0.764473 0.253411 0.146898 0.075 Uiso 1 1 calc R U . . . C14 C 0.4950(7) 0.2932(3) 0.0882(2) 0.0680(11) Uani 1 1 d . . . . . H10 H 0.536635 0.278522 0.039155 0.082 Uiso 1 1 calc R U . . . C15 C 0.2916(7) 0.3305(3) 0.0957(2) 0.0702(11) Uani 1 1 d . . . . . H9 H 0.199268 0.339133 0.051210 0.084 Uiso 1 1 calc R U . . . C9 C 0.1669(6) 0.4191(3) 0.4617(2) 0.0690(11) Uani 1 1 d . . . . . H6B H 0.097093 0.384167 0.499229 0.103 Uiso 1 1 calc R U . . . H6A H 0.083336 0.417166 0.412377 0.103 Uiso 1 1 calc R U . . . H6C H 0.180664 0.480792 0.479090 0.103 Uiso 1 1 calc R U . . . 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 0.0714(4) 0.1232(5) 0.0514(3) 0.0003(2) -0.0005(2) 0.0058(3) O1 0.0511(15) 0.0817(18) 0.0627(17) -0.0031(15) 0.0029(14) 0.0152(14) N2 0.0512(19) 0.0529(18) 0.0463(19) -0.0003(14) 0.0078(17) 0.0038(14) N1 0.0484(18) 0.0559(19) 0.0465(19) 0.0025(15) 0.0067(17) 0.0025(14) C6 0.041(2) 0.0380(19) 0.050(2) -0.0008(16) 0.0100(18) -0.0018(16) C8 0.045(2) 0.043(2) 0.049(2) 0.0024(17) 0.006(2) 0.0002(16) C10 0.042(2) 0.0373(19) 0.054(2) 0.0032(17) 0.0066(19) -0.0004(16) C17 0.051(2) 0.037(2) 0.046(2) -0.0029(16) 0.0031(19) -0.0011(17) C18 0.050(2) 0.037(2) 0.054(2) -0.0037(17) 0.009(2) 0.0000(17) C5 0.040(2) 0.046(2) 0.057(3) -0.0004(18) 0.0055(19) -0.0010(16) C1 0.047(2) 0.046(2) 0.054(3) 0.0006(18) 0.006(2) -0.0003(17) C7 0.043(2) 0.043(2) 0.057(3) 0.0012(18) 0.011(2) -0.0003(16) C00D 0.040(2) 0.043(2) 0.057(2) 0.0018(17) 0.0031(19) 0.0040(16) C11 0.047(2) 0.056(2) 0.055(2) -0.0001(18) -0.0002(18) 0.0065(18) C2 0.046(2) 0.055(2) 0.067(3) -0.008(2) 0.014(2) 0.0024(18) C12 0.044(2) 0.054(2) 0.070(3) -0.004(2) 0.009(2) 0.0097(17) C16 0.062(2) 0.044(2) 0.064(3) -0.003(2) 0.013(2) 0.0068(18) C3 0.061(3) 0.060(2) 0.053(2) -0.0115(19) 0.017(2) -0.006(2) C4 0.051(2) 0.058(2) 0.045(2) -0.0031(17) 0.0062(18) -0.0022(18) C13 0.066(3) 0.052(2) 0.072(3) -0.009(2) 0.017(2) 0.000(2) C14 0.090(3) 0.061(3) 0.054(3) -0.010(2) 0.012(3) -0.005(2) C15 0.088(3) 0.059(3) 0.061(3) -0.002(2) -0.011(2) -0.001(2) C9 0.053(2) 0.095(3) 0.061(3) 0.001(2) 0.0139(19) 0.011(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_ _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 C1 O1 H1 109.5 . . ? C8 N2 N1 113.1(3) . . ? C7 N1 N2 114.6(3) . . ? C5 C6 C1 118.4(3) . . ? C5 C6 C7 120.6(3) . . ? C1 C6 C7 121.0(3) . . ? N2 C8 C10 117.2(3) . . ? N2 C8 C9 122.9(3) . . ? C10 C8 C9 119.9(3) . . ? C00D C10 C11 117.4(3) . . ? C00D C10 C8 122.6(3) . . ? C11 C10 C8 120.0(3) . . ? C00D C17 C18 118.8(3) . . ? C00D C17 C16 122.3(3) . . ? C18 C17 C16 118.9(3) . . ? C17 C18 C13 118.3(3) . . ? C17 C18 C12 118.0(3) . . ? C13 C18 C12 123.6(3) . . ? C4 C5 C6 120.8(3) . . ? C4 C5 H4 119.6 . . ? C6 C5 H4 119.6 . . ? O1 C1 C2 118.4(3) . . ? O1 C1 C6 122.3(3) . . ? C2 C1 C6 119.3(3) . . ? N1 C7 C6 121.0(3) . . ? N1 C7 H5 119.5 . . ? C6 C7 H5 119.5 . . ? C10 C00D C17 122.7(3) . . ? C10 C00D H7 118.6 . . ? C17 C00D H7 118.6 . . ? C12 C11 C10 121.1(3) . . ? C12 C11 H13 119.5 . . ? C10 C11 H13 119.5 . . ? C3 C2 C1 121.0(3) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C11 C12 C18 121.9(3) . . ? C11 C12 H12 119.0 . . ? C18 C12 H12 119.0 . . ? C15 C16 C17 119.8(3) . . ? C15 C16 H8 120.1 . . ? C17 C16 H8 120.1 . . ? C2 C3 C4 119.9(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.5(3) . . ? C5 C4 Br1 120.2(3) . . ? C3 C4 Br1 119.3(3) . . ? C14 C13 C18 121.0(4) . . ? C14 C13 H11 119.5 . . ? C18 C13 H11 119.5 . . ? C13 C14 C15 120.1(4) . . ? C13 C14 H10 119.9 . . ? C15 C14 H10 119.9 . . ? C16 C15 C14 121.8(4) . . ? C16 C15 H9 119.1 . . ? C14 C15 H9 119.1 . . ? C8 C9 H6B 109.5 . . ? C8 C9 H6A 109.5 . . ? H6B C9 H6A 109.5 . . ? C8 C9 H6C 109.5 . . ? H6B C9 H6C 109.5 . . ? H6A C9 H6C 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 Br1 C4 1.892(4) . ? O1 C1 1.346(4) . ? O1 H1 0.8200 . ? N2 C8 1.281(4) . ? N2 N1 1.402(4) . ? N1 C7 1.277(4) . ? C6 C5 1.392(5) . ? C6 C1 1.411(5) . ? C6 C7 1.451(5) . ? C8 C10 1.475(4) . ? C8 C9 1.498(5) . ? C10 C00D 1.375(4) . ? C10 C11 1.419(5) . ? C17 C00D 1.408(4) . ? C17 C18 1.408(4) . ? C17 C16 1.449(5) . ? C18 C13 1.410(5) . ? C18 C12 1.411(5) . ? C5 C4 1.364(5) . ? C5 H4 0.9300 . ? C1 C2 1.380(5) . ? C7 H5 0.9300 . ? C00D H7 0.9300 . ? C11 C12 1.351(5) . ? C11 H13 0.9300 . ? C2 C3 1.366(5) . ? C2 H2 0.9300 . ? C12 H12 0.9300 . ? C16 C15 1.316(5) . ? C16 H8 0.9300 . ? C3 C4 1.377(5) . ? C3 H3 0.9300 . ? C13 C14 1.354(5) . ? C13 H11 0.9300 . ? C14 C15 1.404(5) . ? C14 H10 0.9300 . ? C15 H9 0.9300 . ? C9 H6B 0.9600 . ? C9 H6A 0.9600 . ? C9 H6C 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 C8 N2 N1 C7 178.0(3) . . . . ? N1 N2 C8 C10 -179.0(2) . . . . ? N1 N2 C8 C9 2.9(4) . . . . ? N2 C8 C10 C00D -174.2(3) . . . . ? C9 C8 C10 C00D 4.0(5) . . . . ? N2 C8 C10 C11 5.5(4) . . . . ? C9 C8 C10 C11 -176.4(3) . . . . ? C00D C17 C18 C13 -178.2(3) . . . . ? C16 C17 C18 C13 1.4(4) . . . . ? C00D C17 C18 C12 1.5(4) . . . . ? C16 C17 C18 C12 -178.8(3) . . . . ? C1 C6 C5 C4 -0.7(5) . . . . ? C7 C6 C5 C4 180.0(3) . . . . ? C5 C6 C1 O1 -179.5(3) . . . . ? C7 C6 C1 O1 -0.2(5) . . . . ? C5 C6 C1 C2 0.4(4) . . . . ? C7 C6 C1 C2 179.7(3) . . . . ? N2 N1 C7 C6 -177.8(3) . . . . ? C5 C6 C7 N1 177.8(3) . . . . ? C1 C6 C7 N1 -1.5(5) . . . . ? C11 C10 C00D C17 -0.8(5) . . . . ? C8 C10 C00D C17 178.9(3) . . . . ? C18 C17 C00D C10 -0.6(5) . . . . ? C16 C17 C00D C10 179.7(3) . . . . ? C00D C10 C11 C12 1.4(5) . . . . ? C8 C10 C11 C12 -178.3(3) . . . . ? O1 C1 C2 C3 179.8(3) . . . . ? C6 C1 C2 C3 -0.1(5) . . . . ? C10 C11 C12 C18 -0.6(5) . . . . ? C17 C18 C12 C11 -0.9(5) . . . . ? C13 C18 C12 C11 178.8(3) . . . . ? C00D C17 C16 C15 178.7(3) . . . . ? C18 C17 C16 C15 -1.0(5) . . . . ? C1 C2 C3 C4 0.2(5) . . . . ? C6 C5 C4 C3 0.8(5) . . . . ? C6 C5 C4 Br1 -177.9(2) . . . . ? C2 C3 C4 C5 -0.5(5) . . . . ? C2 C3 C4 Br1 178.2(3) . . . . ? C17 C18 C13 C14 -0.7(5) . . . . ? C12 C18 C13 C14 179.6(3) . . . . ? C18 C13 C14 C15 -0.6(6) . . . . ? C17 C16 C15 C14 -0.3(6) . . . . ? C13 C14 C15 C16 1.1(6) . . . . ?