# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Roger Bishop' 'Donald C. Craig' 'A Norman M. M. Rahman' 'Marcia L. Scudder' _publ_contact_author_name 'Prof Roger Bishop' _publ_contact_author_address ; Chemical Sciences University of New South Wales UNSW Sydney 2052 AUSTRALIA ; _publ_contact_author_email R.BISHOP@UNSW.EDU.AU _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Why a hexabromo diquinoline host selectively includes small aromatic hydrocarbon guests ; data_DRB259_(C22H10Br6N2)2(C6H6)3 _database_code_CSD 201125 _audit_creation_method 'RAELSPUB and manual entry' # TEXT _publ_section_abstract ? _publ_section_comment ? _publ_section_acknowledgements ? _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. De Meulenaer, J. and Tompa, H. Acta Cryst., 1965, 19, 1014. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee, U.S.A., 1976. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1989. ; _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ? _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'RAELS, (Rae, 1989)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C22 H10 Br6 N2, 1.5(C6 H6)' _chemical_formula_sum 'C31 H19 Br6 N2' _chemical_formula_iupac ? _chemical_formula_weight 898.9 # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 9.589(6) _cell_length_b 13.179(7) _cell_length_c 13.454(7) _cell_angle_alpha 110.43(3) _cell_angle_beta 100.31(3) _cell_angle_gamma 101.43(3) _cell_volume 1504(1) _cell_formula_units_Z 2 _cell_measurement_reflns_used 10 _cell_measurement_theta_min 12 _cell_measurement_theta_max 13 _cell_measurement_temperature 294 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.99 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 858.0 _exptl_absorpt_coefficient_mu 7.957 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(DeMeulenaer & Tompa, 1965)' _exptl_absorpt_correction_T_min 0.26 _exptl_absorpt_correction_T_max 0.39 # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 5521 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_theta_max 25 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 5 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 5273 _reflns_number_gt 3538 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.043 _refine_ls_wR_factor_ref 0.051 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 3538 _refine_ls_number_parameters 172 _refine_ls_goodness_of_fit_ref 1.60 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.005 _refine_diff_density_max 1.33 _refine_diff_density_min -1.22 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy Br1 0.46072(9) -0.07892(6) 0.34839(6) 0.0595(2) Uani Br 1.0 Br2 1.12261(8) 0.08404(7) 0.38410(7) 0.0604(2) Uani Br 1.0 Br3 0.79526(8) 0.15406(7) -0.03739(6) 0.0561(2) Uani Br 1.0 Br4 0.17649(9) 0.17026(8) 0.10093(8) 0.0783(3) Uani Br 1.0 Br5 0.71453(10) 0.37371(7) 0.79131(6) 0.0702(3) Uani Br 1.0 Br6 1.26513(8) 0.59790(6) 0.64062(6) 0.0573(2) Uani Br 1.0 N1 0.7163(5) 0.1129(4) 0.1566(4) 0.0348(5) Uani N 1.0 N2 0.8057(6) 0.2626(4) 0.5836(4) 0.0381(5) Uani N 1.0 C1 0.8084(7) 0.0661(5) 0.3152(5) 0.0373(5) Uani C 1.0 C2 0.6956(6) 0.0937(5) 0.2437(5) 0.0338(5) Uani C 1.0 C3 0.5684(6) 0.0970(5) 0.2811(5) 0.0356(5) Uani C 1.0 C4 0.5865(7) 0.0745(5) 0.3825(5) 0.0399(6) Uani C 1.0 C5 0.7506(7) 0.0833(5) 0.4187(5) 0.0391(5) Uani C 1.0 C6 0.8409(7) 0.2039(5) 0.4960(5) 0.0361(5) Uani C 1.0 C7 0.9587(7) 0.2425(5) 0.4580(5) 0.0360(5) Uani C 1.0 C8 0.9614(7) 0.1531(5) 0.3537(5) 0.0384(7) Uani C 1.0 C9 0.6032(7) 0.1375(5) 0.1003(5) 0.0367(6) Uani C 1.0 C10 0.6218(7) 0.1615(5) 0.0073(5) 0.0429(8) Uani C 1.0 C11 0.5131(8) 0.1895(6) -0.0503(5) 0.0504(9) Uani C 1.0 C12 0.3814(8) 0.1925(6) -0.0202(5) 0.053(1) Uani C 1.0 C13 0.3586(7) 0.1691(6) 0.0669(5) 0.047(1) Uani C 1.0 C14 0.4688(7) 0.1425(5) 0.1307(5) 0.0390(7) Uani C 1.0 C15 0.4536(6) 0.1189(5) 0.2249(5) 0.0386(7) Uani C 1.0 C16 0.8931(7) 0.3704(5) 0.6423(5) 0.0382(5) Uani C 1.0 C17 0.8637(7) 0.4393(5) 0.7403(5) 0.0435(8) Uani C 1.0 C18 0.9425(8) 0.5475(6) 0.7975(5) 0.047(1) Uani C 1.0 C19 1.0593(7) 0.5969(5) 0.7655(5) 0.047(1) Uani C 1.0 C20 1.0960(7) 0.5335(5) 0.6764(5) 0.044(1) Uani C 1.0 C21 1.0152(7) 0.4189(5) 0.6096(5) 0.0384(6) Uani C 1.0 C22 1.0481(6) 0.3497(5) 0.5145(5) 0.0382(6) Uani C 1.0 C1Bz1 0.5105(9) 0.4213(6) 0.5430(7) 0.089(3) Uani C 0.5 C2Bz1 0.5926(7) 0.5309(7) 0.6017(3) 0.089(3) Uani C 0.5 C3Bz1 0.5821(7) 0.6096(3) 0.5588(6) 0.087(3) Uani C 0.5 C4Bz1 0.4895(9) 0.5787(6) 0.4570(7) 0.089(3) Uani C 0.5 C5Bz1 0.4074(7) 0.4691(7) 0.3983(3) 0.089(3) Uani C 0.5 C6Bz1 0.4179(7) 0.3904(3) 0.4412(6) 0.087(3) Uani C 0.5 C1Bz2 0.1240(9) 0.3576(8) 0.8833(5) 0.112(5) Uani C 1.0 C2Bz2 0.2532(9) 0.4328(5) 0.8967(5) 0.122(6) Uani C 1.0 C3Bz2 0.3335(6) 0.4065(6) 0.8221(7) 0.107(4) Uani C 1.0 C4Bz2 0.2846(7) 0.3048(7) 0.7341(6) 0.088(2) Uani C 1.0 C5Bz2 0.1553(8) 0.2295(5) 0.7208(5) 0.086(3) Uani C 1.0 C6Bz2 0.0750(6) 0.2559(6) 0.7954(7) 0.096(3) Uani C 1.0 HC1 0.8135 -0.0129 0.2788 0.043 Uani H 1.0 HC4 0.5594 0.1324 0.4409 0.041 Uani H 1.0 HC5 0.7674 0.0274 0.4509 0.046 Uani H 1.0 HC8 0.9748 0.1852 0.2977 0.038 Uani H 1.0 HC11 0.5284 0.2079 -0.1144 0.058 Uani H 1.0 HC12 0.3029 0.2122 -0.0635 0.062 Uani H 1.0 HC15 0.3606 0.1184 0.2488 0.044 Uani H 1.0 HC18 0.9169 0.5938 0.8645 0.053 Uani H 1.0 HC19 1.1154 0.6783 0.8081 0.054 Uani H 1.0 HC22 1.1342 0.3789 0.4898 0.043 Uani H 1.0 HC1Bz1 0.5182 0.3635 0.5745 0.130 Uani H 0.5 HC2Bz1 0.6605 0.5535 0.6763 0.129 Uani H 0.5 HC3Bz1 0.6423 0.6900 0.6019 0.124 Uani H 0.5 HC4Bz1 0.4818 0.6365 0.4255 0.130 Uani H 0.5 HC5Bz1 0.3395 0.4465 0.3237 0.129 Uani H 0.5 HC6Bz1 0.3577 0.3100 0.3981 0.124 Uani H 0.5 HC1Bz2 0.0651 0.3769 0.9380 0.160 Uani H 1.0 HC2Bz2 0.2891 0.5074 0.9612 0.181 Uani H 1.0 HC3Bz2 0.4282 0.4616 0.8319 0.154 Uani H 1.0 HC4Bz2 0.3434 0.2855 0.6794 0.118 Uani H 1.0 HC5Bz2 0.1195 0.1550 0.6563 0.119 Uani H 1.0 HC6Bz2 -0.0197 0.2007 0.7856 0.134 Uani H 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol Br1 0.0740(5) 0.0455(4) 0.0376(4) -0.0197(4) 0.0071(4) 0.0154(3) Br Br2 0.0522(5) 0.0581(5) 0.0653(5) 0.0208(4) 0.0095(4) 0.0183(4) Br Br3 0.0532(4) 0.0704(5) 0.0376(4) 0.0030(4) 0.0137(3) 0.0203(4) Br Br4 0.0542(5) 0.1040(7) 0.0851(7) 0.0369(5) 0.0182(5) 0.0400(6) Br Br5 0.0828(6) 0.0569(5) 0.0557(5) -0.0039(4) 0.0351(4) 0.0096(4) Br Br6 0.0450(4) 0.0404(4) 0.0710(5) -0.0035(3) 0.0148(4) 0.0129(4) Br N1 0.0374(8) 0.0297(8) 0.0309(7) 0.0025(7) 0.0068(7) 0.0097(6) N N2 0.045(1) 0.0333(8) 0.0312(7) 0.0027(8) 0.0074(6) 0.0132(7) N C1 0.044(1) 0.0282(9) 0.0347(8) 0.0058(8) 0.0057(7) 0.0109(6) C C2 0.0368(9) 0.0266(9) 0.0319(7) 0.0015(7) 0.0062(6) 0.0101(6) C C3 0.0362(9) 0.0289(9) 0.0338(8) -0.0017(8) 0.0068(6) 0.0106(6) C C4 0.045(1) 0.031(1) 0.0365(9) -0.004(1) 0.0093(8) 0.0134(7) C C5 0.049(1) 0.0285(9) 0.0351(8) 0.0027(8) 0.0067(8) 0.0140(7) C C6 0.042(1) 0.0299(8) 0.0320(7) 0.0037(7) 0.0057(6) 0.0127(6) C C7 0.036(1) 0.0322(8) 0.0331(7) 0.0047(7) 0.0045(6) 0.0107(6) C C8 0.038(1) 0.035(1) 0.0356(8) 0.008(1) 0.0055(7) 0.0099(7) C C9 0.0401(8) 0.0324(8) 0.0307(7) 0.0030(7) 0.0050(6) 0.0105(6) C C10 0.052(1) 0.039(1) 0.0309(7) 0.005(1) 0.0061(7) 0.0131(7) C C11 0.064(2) 0.047(2) 0.0331(8) 0.011(2) 0.0020(8) 0.0155(9) C C12 0.059(2) 0.051(2) 0.037(1) 0.015(2) -0.003(1) 0.013(1) C C13 0.045(1) 0.047(2) 0.038(1) 0.010(1) -0.0015(9) 0.0099(9) C C14 0.0374(9) 0.0361(9) 0.0338(8) 0.0037(7) 0.0026(6) 0.0096(6) C C15 0.034(1) 0.036(1) 0.0358(9) -0.0005(8) 0.0052(6) 0.0093(7) C C16 0.043(1) 0.0341(9) 0.0305(7) 0.0034(7) 0.0055(6) 0.0105(6) C C17 0.050(2) 0.041(1) 0.0307(7) 0.005(1) 0.0075(7) 0.0093(7) C C18 0.053(2) 0.041(2) 0.0323(7) 0.005(1) 0.0052(8) 0.0055(8) C C19 0.051(2) 0.037(1) 0.0358(8) 0.001(1) 0.002(1) 0.0041(9) C C20 0.043(1) 0.036(1) 0.0365(8) -0.0018(9) 0.0020(8) 0.0062(8) C C21 0.038(1) 0.0336(9) 0.0329(7) 0.0014(6) 0.0032(7) 0.0087(6) C C22 0.034(1) 0.035(1) 0.0347(8) 0.0018(6) 0.0039(6) 0.0093(7) C C1Bz1 0.102(7) 0.100(5) 0.097(5) 0.051(4) 0.055(4) 0.052(4) C C2Bz1 0.070(5) 0.121(5) 0.071(5) 0.043(4) 0.018(3) 0.025(4) C C3Bz1 0.065(5) 0.080(5) 0.101(5) 0.013(4) 0.036(4) 0.017(4) C C4Bz1 0.102(7) 0.100(5) 0.097(5) 0.051(4) 0.055(4) 0.052(4) C C5Bz1 0.070(5) 0.121(5) 0.071(5) 0.043(4) 0.018(3) 0.025(4) C C6Bz1 0.065(5) 0.080(5) 0.101(5) 0.013(4) 0.036(4) 0.017(4) C C1Bz2 0.136(6) 0.172(9) 0.071(4) 0.098(6) 0.042(4) 0.060(4) C C2Bz2 0.132(6) 0.116(7) 0.092(5) 0.071(5) -0.007(4) 0.010(5) C C3Bz2 0.094(4) 0.092(6) 0.138(7) 0.034(4) 0.012(4) 0.054(5) C C4Bz2 0.098(4) 0.115(6) 0.083(5) 0.051(4) 0.038(3) 0.060(4) C C5Bz2 0.097(4) 0.090(5) 0.076(5) 0.041(4) 0.019(3) 0.034(4) C C6Bz2 0.097(4) 0.123(5) 0.109(5) 0.051(4) 0.042(3) 0.077(4) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C4 1.985(6) 1_555 1_555 no Br2 C8 1.994(6) 1_555 1_555 no Br3 C10 1.876(7) 1_555 1_555 no Br4 C13 1.884(7) 1_555 1_555 no Br5 C17 1.882(6) 1_555 1_555 no Br6 C20 1.897(6) 1_555 1_555 no N1 C2 1.322(7) 1_555 1_555 no N1 C9 1.368(7) 1_555 1_555 no N2 C6 1.309(7) 1_555 1_555 no N2 C16 1.361(7) 1_555 1_555 no C1 C2 1.502(8) 1_555 1_555 no C1 C5 1.550(8) 1_555 1_555 no C1 C8 1.543(8) 1_555 1_555 no C2 C3 1.403(8) 1_555 1_555 no C3 C4 1.483(8) 1_555 1_555 no C3 C15 1.359(8) 1_555 1_555 no C4 C5 1.530(9) 1_555 1_555 no C5 C6 1.528(8) 1_555 1_555 no C6 C7 1.398(8) 1_555 1_555 no C7 C8 1.493(8) 1_555 1_555 no C7 C22 1.359(8) 1_555 1_555 no C9 C10 1.426(8) 1_555 1_555 no C9 C14 1.427(8) 1_555 1_555 no C10 C11 1.373(9) 1_555 1_555 no C11 C12 1.397(9) 1_555 1_555 no C12 C13 1.354(9) 1_555 1_555 no C13 C14 1.417(9) 1_555 1_555 no C14 C15 1.430(9) 1_555 1_555 no C16 C17 1.428(8) 1_555 1_555 no C16 C21 1.435(8) 1_555 1_555 no C17 C18 1.340(8) 1_555 1_555 no C18 C19 1.394(9) 1_555 1_555 no C19 C20 1.352(9) 1_555 1_555 no C20 C21 1.425(8) 1_555 1_555 no C21 C22 1.418(8) 1_555 1_555 no C1Bz1 C2Bz1 1.364(3) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C9 116.0(5) 1_555 1_555 1_555 no C6 N2 C16 116.2(5) 1_555 1_555 1_555 no C2 C1 C5 102.3(5) 1_555 1_555 1_555 no C2 C1 C8 111.7(5) 1_555 1_555 1_555 no C5 C1 C8 106.6(5) 1_555 1_555 1_555 no N1 C2 C1 123.1(5) 1_555 1_555 1_555 no N1 C2 C3 125.0(5) 1_555 1_555 1_555 no C1 C2 C3 111.9(5) 1_555 1_555 1_555 no C2 C3 C4 109.8(5) 1_555 1_555 1_555 no C2 C3 C15 119.8(5) 1_555 1_555 1_555 no C4 C3 C15 130.4(6) 1_555 1_555 1_555 no Br1 C4 C3 109.6(4) 1_555 1_555 1_555 no Br1 C4 C5 111.3(4) 1_555 1_555 1_555 no C3 C4 C5 105.0(5) 1_555 1_555 1_555 no C1 C5 C4 106.3(5) 1_555 1_555 1_555 no C1 C5 C6 102.0(5) 1_555 1_555 1_555 no C4 C5 C6 111.5(5) 1_555 1_555 1_555 no N2 C6 C5 122.7(5) 1_555 1_555 1_555 no N2 C6 C7 125.8(5) 1_555 1_555 1_555 no C5 C6 C7 111.5(5) 1_555 1_555 1_555 no C6 C7 C8 110.5(5) 1_555 1_555 1_555 no C6 C7 C22 119.6(6) 1_555 1_555 1_555 no C8 C7 C22 129.8(6) 1_555 1_555 1_555 no Br2 C8 C1 110.9(4) 1_555 1_555 1_555 no Br2 C8 C7 109.9(4) 1_555 1_555 1_555 no C1 C8 C7 104.1(5) 1_555 1_555 1_555 no N1 C9 C10 118.1(6) 1_555 1_555 1_555 no N1 C9 C14 123.7(5) 1_555 1_555 1_555 no C10 C9 C14 118.2(6) 1_555 1_555 1_555 no Br3 C10 C9 119.9(5) 1_555 1_555 1_555 no Br3 C10 C11 119.7(5) 1_555 1_555 1_555 no C9 C10 C11 120.4(6) 1_555 1_555 1_555 no C10 C11 C12 120.6(6) 1_555 1_555 1_555 no C11 C12 C13 120.9(6) 1_555 1_555 1_555 no Br4 C13 C12 118.9(5) 1_555 1_555 1_555 no Br4 C13 C14 120.3(5) 1_555 1_555 1_555 no C12 C13 C14 120.7(6) 1_555 1_555 1_555 no C9 C14 C13 119.2(6) 1_555 1_555 1_555 no C9 C14 C15 116.9(5) 1_555 1_555 1_555 no C13 C14 C15 123.9(6) 1_555 1_555 1_555 no C3 C15 C14 118.5(6) 1_555 1_555 1_555 no N2 C16 C17 119.7(5) 1_555 1_555 1_555 no N2 C16 C21 122.5(5) 1_555 1_555 1_555 no C17 C16 C21 117.9(5) 1_555 1_555 1_555 no Br5 C17 C16 118.5(5) 1_555 1_555 1_555 no Br5 C17 C18 119.9(5) 1_555 1_555 1_555 no C16 C17 C18 121.6(6) 1_555 1_555 1_555 no C17 C18 C19 121.4(6) 1_555 1_555 1_555 no C18 C19 C20 119.3(6) 1_555 1_555 1_555 no Br6 C20 C19 119.0(5) 1_555 1_555 1_555 no Br6 C20 C21 118.3(5) 1_555 1_555 1_555 no C19 C20 C21 122.7(6) 1_555 1_555 1_555 no C16 C21 C20 117.2(6) 1_555 1_555 1_555 no C16 C21 C22 118.2(5) 1_555 1_555 1_555 no C20 C21 C22 124.7(6) 1_555 1_555 1_555 no C7 C22 C21 117.7(6) 1_555 1_555 1_555 no C2Bz1 C1Bz1 C6Bz1 120.0 1_555 1_555 1_555 no data_DRB265_C22H10Br6N2,C8H10 _database_code_CSD 201126 _audit_creation_method 'RAELSPUB and manual entry' # TEXT _publ_section_abstract ? _publ_section_comment ? _publ_section_acknowledgements ? _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. De Meulenaer, J. and Tompa, H. Acta Cryst., 1965, 19, 1014. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee, U.S.A., 1976. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1989. ; _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ? _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'RAELS, (Rae, 1989)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C22 H10 Br6 N2,C8 H10' _chemical_formula_sum 'C30 H20 Br6 N2' _chemical_formula_iupac ? _chemical_formula_weight 887.9 # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 10.107(5) _cell_length_b 11.121(5) _cell_length_c 14.410(7) _cell_angle_alpha 74.44(4) _cell_angle_beta 72.35(4) _cell_angle_gamma 79.62(3) _cell_volume 1478(1) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 15 _cell_measurement_temperature 294 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.03 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.99 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848.0 _exptl_absorpt_coefficient_mu 8.092 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(DeMeulenaer & Tompa, 1965)' _exptl_absorpt_correction_T_min 0.19 _exptl_absorpt_correction_T_max 0.60 # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 5409 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_theta_max 25 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 0 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 5182 _reflns_number_gt 2676 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.079 _refine_ls_wR_factor_ref 0.096 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2676 _refine_ls_number_parameters 169 _refine_ls_goodness_of_fit_ref 1.72 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.002 _refine_diff_density_max 1.77 _refine_diff_density_min -1.88 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy Br1 0.9814(2) 0.1083(2) 0.7670(1) 0.0672(5) Uani Br 1.0 Br2 0.7295(2) -0.0492(2) 0.4933(2) 0.0862(6) Uani Br 1.0 Br3 0.2276(2) -0.0587(2) 0.8970(2) 0.0898(7) Uani Br 1.0 Br4 0.4654(3) 0.3346(3) 1.0550(2) 0.1078(8) Uani Br 1.0 Br5 0.8811(2) 0.6232(1) 0.4549(1) 0.0630(5) Uani Br 1.0 Br6 0.4264(2) 0.4373(2) 0.2991(1) 0.0819(6) Uani Br 1.0 N1 0.5045(11) 0.0485(10) 0.8034(9) 0.054(2) Uani N 1.0 N2 0.7891(11) 0.3633(10) 0.5160(7) 0.042(2) Uani N 1.0 C1 0.7173(14) 0.0495(12) 0.6637(10) 0.049(3) Uani C 1.0 C2 0.6290(14) 0.0861(12) 0.7559(10) 0.049(2) Uani C 1.0 C3 0.6905(14) 0.1699(13) 0.7863(9) 0.047(2) Uani C 1.0 C4 0.8262(14) 0.1994(12) 0.7113(10) 0.046(2) Uani C 1.0 C5 0.8250(13) 0.1487(12) 0.6221(10) 0.046(2) Uani C 1.0 C6 0.7579(13) 0.2469(12) 0.5486(9) 0.043(2) Uani C 1.0 C7 0.6535(14) 0.1981(12) 0.5266(10) 0.046(2) Uani C 1.0 C8 0.6393(14) 0.0656(13) 0.5847(11) 0.052(3) Uani C 1.0 C9 0.4321(15) 0.0939(14) 0.8878(11) 0.058(2) Uani C 1.0 C10 0.2987(16) 0.0547(15) 0.9385(12) 0.069(2) Uani C 1.0 C11 0.2163(17) 0.1046(17) 1.0161(12) 0.079(2) Uani C 1.0 C12 0.2714(18) 0.1829(18) 1.0528(11) 0.081(2) Uani C 1.0 C13 0.4018(17) 0.2203(17) 1.0073(10) 0.071(2) Uani C 1.0 C14 0.4867(15) 0.1766(15) 0.9220(10) 0.059(2) Uani C 1.0 C15 0.6211(15) 0.2159(14) 0.8673(10) 0.053(2) Uani C 1.0 C16 0.7192(13) 0.4440(12) 0.4507(9) 0.043(2) Uani C 1.0 C17 0.7489(14) 0.5652(13) 0.4152(9) 0.047(2) Uani C 1.0 C18 0.6834(14) 0.6493(13) 0.3464(10) 0.052(2) Uani C 1.0 C19 0.5899(15) 0.6064(14) 0.3136(9) 0.054(2) Uani C 1.0 C20 0.5560(15) 0.4896(14) 0.3478(9) 0.051(3) Uani C 1.0 C21 0.6158(14) 0.3991(13) 0.4190(9) 0.045(2) Uani C 1.0 C22 0.5838(14) 0.2755(13) 0.4594(9) 0.047(3) Uani C 1.0 C1Ox 0.8927(18) 0.4344(22) 0.1643(10) 0.147(9) Uani C 1.0 C2Ox 0.9976(19) 0.4633(18) 0.1950(14) 0.160(9) Uani C 1.0 C3Ox 1.0522(17) 0.3772(32) 0.2662(15) 0.261(9) Uani C 1.0 C4Ox 1.0013(29) 0.2635(26) 0.3059(11) 0.338(9) Uani C 1.0 C5Ox 0.8958(31) 0.2346(17) 0.2749(18) 0.329(9) Uani C 1.0 C6Ox 0.8416(19) 0.3194(27) 0.2045(18) 0.238(9) Uani C 1.0 C7Ox 0.8384(40) 0.5182(47) 0.0944(17) 0.344(9) Uani C 1.0 C8Ox 1.0486(47) 0.5759(32) 0.1560(31) 0.372(9) Uani C 1.0 HC1 0.7648 -0.0377 0.6786 0.056 Uani H 1.0 HC4 0.8331 0.2919 0.6911 0.045 Uani H 1.0 HC5 0.9199 0.1125 0.5884 0.050 Uani H 1.0 HC8 0.5389 0.0521 0.6167 0.053 Uani H 1.0 HC11 0.1173 0.0855 1.0464 0.088 Uani H 1.0 HC12 0.2140 0.2123 1.1141 0.093 Uani H 1.0 HC15 0.6624 0.2758 0.8885 0.057 Uani H 1.0 HC18 0.7043 0.7387 0.3217 0.058 Uani H 1.0 HC19 0.5463 0.6650 0.2624 0.060 Uani H 1.0 HC22 0.5120 0.2434 0.4401 0.053 Uani H 1.0 HC3Ox 1.1282 0.3980 0.2886 0.475 Uani H 1.0 HC4Ox 1.0403 0.2005 0.3576 0.605 Uani H 1.0 HC5Ox 0.8594 0.1508 0.3046 0.590 Uani H 1.0 HC6Ox 0.7656 0.2984 0.1823 0.437 Uani H 1.0 H1C7Ox 0.7642 0.4811 0.0818 0.504 Uani H 1.0 H2C7Ox 0.7970 0.5964 0.1189 0.460 Uani H 1.0 H3C7Ox 0.9139 0.5390 0.0309 0.384 Uani H 1.0 H1C8Ox 1.1234 0.5798 0.1870 0.551 Uani H 1.0 H2C8Ox 1.0885 0.5869 0.0821 0.396 Uani H 1.0 H3C8Ox 0.9716 0.6444 0.1700 0.496 Uani H 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol Br1 0.050(1) 0.065(1) 0.080(1) -0.0050(8) -0.0338(8) 0.0119(8) Br Br2 0.099(2) 0.061(1) 0.110(1) 0.000(1) -0.025(1) -0.048(1) Br Br3 0.059(1) 0.076(1) 0.127(2) -0.018(1) -0.033(1) 0.006(1) Br Br4 0.103(2) 0.128(2) 0.109(2) 0.015(1) -0.035(1) -0.065(1) Br Br5 0.070(1) 0.0438(9) 0.079(1) -0.0160(8) -0.0289(8) -0.0027(7) Br Br6 0.069(1) 0.105(2) 0.085(1) -0.004(1) -0.046(1) -0.020(1) Br N1 0.043(3) 0.038(2) 0.071(4) -0.002(2) -0.018(2) 0.006(2) N N2 0.040(3) 0.036(2) 0.047(4) 0.001(2) -0.013(2) -0.007(2) N C1 0.043(3) 0.032(2) 0.071(5) 0.001(2) -0.020(2) -0.007(2) C C2 0.042(2) 0.036(2) 0.062(4) -0.001(2) -0.019(2) 0.001(2) C C3 0.045(2) 0.042(2) 0.052(4) 0.000(2) -0.020(2) 0.001(2) C C4 0.042(2) 0.038(3) 0.056(5) 0.000(2) -0.021(2) -0.002(2) C C5 0.041(2) 0.034(2) 0.060(5) 0.001(2) -0.017(2) -0.007(2) C C6 0.041(3) 0.035(2) 0.051(4) 0.002(2) -0.015(2) -0.011(2) C C7 0.047(3) 0.037(2) 0.057(3) 0.003(2) -0.019(2) -0.017(2) C C8 0.049(5) 0.034(2) 0.076(4) 0.003(2) -0.023(3) -0.018(2) C C9 0.047(3) 0.051(2) 0.061(3) -0.001(2) -0.015(2) 0.012(2) C C10 0.049(4) 0.058(3) 0.074(4) -0.001(3) -0.012(2) 0.021(3) C C11 0.056(4) 0.078(5) 0.066(4) 0.003(3) -0.006(3) 0.025(3) C C12 0.068(5) 0.094(5) 0.048(3) 0.009(4) -0.008(3) 0.015(2) C C13 0.067(5) 0.085(5) 0.043(3) 0.008(3) -0.015(2) 0.005(2) C C14 0.054(3) 0.062(3) 0.047(3) 0.003(2) -0.017(2) 0.006(2) C C15 0.052(3) 0.056(3) 0.047(3) 0.002(2) -0.022(2) 0.000(2) C C16 0.042(3) 0.040(2) 0.043(3) 0.002(2) -0.012(2) -0.007(2) C C17 0.041(3) 0.042(2) 0.049(3) 0.000(2) -0.011(2) -0.001(2) C C18 0.045(2) 0.050(2) 0.048(3) 0.001(2) -0.010(2) 0.003(2) C C19 0.052(3) 0.059(3) 0.041(4) 0.004(2) -0.014(2) -0.003(2) C C20 0.055(3) 0.057(3) 0.041(4) 0.006(2) -0.018(2) -0.013(2) C C21 0.049(3) 0.046(2) 0.042(3) 0.004(2) -0.016(2) -0.014(2) C C22 0.052(4) 0.044(2) 0.053(3) 0.005(2) -0.021(2) -0.021(2) C C1Ox 0.129(9) 0.147(9) 0.116(9) 0.042(9) 0.029(9) -0.056(9) C C2Ox 0.156(9) 0.135(9) 0.153(9) -0.027(9) 0.065(9) -0.089(9) C C3Ox 0.131(9) 0.474(9) 0.138(9) 0.077(9) 0.019(9) -0.140(9) C C4Ox 0.335(9) 0.298(9) 0.135(9) 0.238(9) 0.082(9) 0.016(9) C C5Ox 0.448(9) 0.070(9) 0.261(9) -0.015(9) 0.217(9) -0.060(9) C C6Ox 0.218(9) 0.258(9) 0.227(9) -0.109(9) 0.119(9) -0.184(9) C C7Ox 0.235(9) 0.506(9) 0.115(9) 0.239(9) 0.028(9) -0.048(9) C C8Ox 0.428(9) 0.247(9) 0.347(9) -0.214(9) 0.267(9) -0.221(9) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C4 1.971(13) 1_555 1_555 no Br2 C8 1.987(14) 1_555 1_555 no Br3 C10 1.859(19) 1_555 1_555 no Br4 C13 1.880(19) 1_555 1_555 no Br5 C17 1.870(14) 1_555 1_555 no Br6 C20 1.897(14) 1_555 1_555 no N1 C2 1.319(16) 1_555 1_555 no N1 C9 1.387(18) 1_555 1_555 no N2 C6 1.314(16) 1_555 1_555 no N2 C16 1.383(15) 1_555 1_555 no C1 C2 1.472(19) 1_555 1_555 no C1 C5 1.563(19) 1_555 1_555 no C1 C8 1.528(19) 1_555 1_555 no C2 C3 1.428(19) 1_555 1_555 no C3 C4 1.494(18) 1_555 1_555 no C3 C15 1.345(19) 1_555 1_555 no C4 C5 1.540(19) 1_555 1_555 no C5 C6 1.524(17) 1_555 1_555 no C6 C7 1.417(18) 1_555 1_555 no C7 C8 1.495(19) 1_555 1_555 no C7 C22 1.387(17) 1_555 1_555 no C9 C10 1.409(20) 1_555 1_555 no C9 C14 1.410(21) 1_555 1_555 no C10 C11 1.361(23) 1_555 1_555 no C11 C12 1.396(26) 1_555 1_555 no C12 C13 1.367(23) 1_555 1_555 no C13 C14 1.419(21) 1_555 1_555 no C14 C15 1.426(20) 1_555 1_555 no C16 C17 1.361(18) 1_555 1_555 no C16 C21 1.466(18) 1_555 1_555 no C17 C18 1.405(17) 1_555 1_555 no C18 C19 1.378(19) 1_555 1_555 no C19 C20 1.328(20) 1_555 1_555 no C20 C21 1.426(17) 1_555 1_555 no C21 C22 1.396(19) 1_555 1_555 no C1Ox C2Ox 1.381(16) 1_555 1_555 no C1Ox C6Ox 1.378(11) 1_555 1_555 no C1Ox C7Ox 1.353(26) 1_555 1_555 no C2Ox C3Ox 1.378(11) 1_555 1_555 no C2Ox C8Ox 1.353(26) 1_555 1_555 no C3Ox C4Ox 1.363(13) 1_555 1_555 no C4Ox C5Ox 1.389(17) 1_555 1_555 no C5Ox C6Ox 1.363(13) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C9 116.7(13) 1_555 1_555 1_555 no C6 N2 C16 117.4(11) 1_555 1_555 1_555 no C2 C1 C5 102.3(11) 1_555 1_555 1_555 no C2 C1 C8 113.4(11) 1_555 1_555 1_555 no C5 C1 C8 106.9(11) 1_555 1_555 1_555 no N1 C2 C1 123.4(14) 1_555 1_555 1_555 no N1 C2 C3 123.7(13) 1_555 1_555 1_555 no C1 C2 C3 112.8(12) 1_555 1_555 1_555 no C2 C3 C4 109.1(12) 1_555 1_555 1_555 no C2 C3 C15 120.3(13) 1_555 1_555 1_555 no C4 C3 C15 130.4(14) 1_555 1_555 1_555 no Br1 C4 C3 109.4(8) 1_555 1_555 1_555 no Br1 C4 C5 109.7(9) 1_555 1_555 1_555 no C3 C4 C5 104.3(11) 1_555 1_555 1_555 no C1 C5 C4 106.6(11) 1_555 1_555 1_555 no C1 C5 C6 101.3(10) 1_555 1_555 1_555 no C4 C5 C6 111.8(11) 1_555 1_555 1_555 no N2 C6 C5 123.0(12) 1_555 1_555 1_555 no N2 C6 C7 125.7(12) 1_555 1_555 1_555 no C5 C6 C7 111.2(11) 1_555 1_555 1_555 no C6 C7 C8 110.2(11) 1_555 1_555 1_555 no C6 C7 C22 118.3(12) 1_555 1_555 1_555 no C8 C7 C22 131.5(13) 1_555 1_555 1_555 no Br2 C8 C1 111.1(9) 1_555 1_555 1_555 no Br2 C8 C7 108.9(9) 1_555 1_555 1_555 no C1 C8 C7 104.2(11) 1_555 1_555 1_555 no N1 C9 C10 117.1(16) 1_555 1_555 1_555 no N1 C9 C14 122.5(13) 1_555 1_555 1_555 no C10 C9 C14 120.5(15) 1_555 1_555 1_555 no Br3 C10 C9 121.1(14) 1_555 1_555 1_555 no Br3 C10 C11 118.6(13) 1_555 1_555 1_555 no C9 C10 C11 120.2(18) 1_555 1_555 1_555 no C10 C11 C12 119.3(16) 1_555 1_555 1_555 no C11 C12 C13 121.8(17) 1_555 1_555 1_555 no Br4 C13 C12 119.8(14) 1_555 1_555 1_555 no Br4 C13 C14 120.2(12) 1_555 1_555 1_555 no C12 C13 C14 120.0(18) 1_555 1_555 1_555 no C9 C14 C13 117.7(14) 1_555 1_555 1_555 no C9 C14 C15 118.7(14) 1_555 1_555 1_555 no C13 C14 C15 123.6(16) 1_555 1_555 1_555 no C3 C15 C14 118.1(14) 1_555 1_555 1_555 no N2 C16 C17 119.1(12) 1_555 1_555 1_555 no N2 C16 C21 120.4(12) 1_555 1_555 1_555 no C17 C16 C21 120.5(12) 1_555 1_555 1_555 no Br5 C17 C16 120.8(10) 1_555 1_555 1_555 no Br5 C17 C18 118.3(11) 1_555 1_555 1_555 no C16 C17 C18 121.0(13) 1_555 1_555 1_555 no C17 C18 C19 118.8(13) 1_555 1_555 1_555 no C18 C19 C20 122.1(13) 1_555 1_555 1_555 no Br6 C20 C19 119.6(10) 1_555 1_555 1_555 no Br6 C20 C21 117.7(11) 1_555 1_555 1_555 no C19 C20 C21 122.6(13) 1_555 1_555 1_555 no C16 C21 C20 115.0(12) 1_555 1_555 1_555 no C16 C21 C22 119.2(11) 1_555 1_555 1_555 no C20 C21 C22 125.8(13) 1_555 1_555 1_555 no C7 C22 C21 118.8(12) 1_555 1_555 1_555 no C2Ox C1Ox C6Ox 120.3(4) 1_555 1_555 1_555 no C2Ox C1Ox C7Ox 120.8(18) 1_555 1_555 1_555 no C6Ox C1Ox C7Ox 118.9(19) 1_555 1_555 1_555 no C1Ox C2Ox C3Ox 120.3(4) 1_555 1_555 1_555 no C1Ox C2Ox C8Ox 120.8(18) 1_555 1_555 1_555 no C3Ox C2Ox C8Ox 118.9(19) 1_555 1_555 1_555 no C2Ox C3Ox C4Ox 119.2(7) 1_555 1_555 1_555 no C3Ox C4Ox C5Ox 120.5(4) 1_555 1_555 1_555 no C4Ox C5Ox C6Ox 120.5(4) 1_555 1_555 1_555 no C1Ox C6Ox C5Ox 119.2(7) 1_555 1_555 1_555 no data_DRB264_C22H10Br6N2,C8H10 _database_code_CSD 201127 _audit_creation_method 'RAELSPUB and manual entry' # TEXT _publ_section_abstract ? _publ_section_comment ? _publ_section_acknowledgements ? _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. De Meulenaer, J. and Tompa, H. Acta Cryst., 1965, 19, 1014. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee, U.S.A., 1976. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1989. ; _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ? _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'RAELS, (Rae, 1989)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C22 H10 Br6 N2,C8 H10' _chemical_formula_sum 'C30 H20 Br6 N2' _chemical_formula_iupac ? _chemical_formula_weight 887.9 # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 9.596(5) _cell_length_b 12.682(6) _cell_length_c 13.545(7) _cell_angle_alpha 107.47(3) _cell_angle_beta 96.61(3) _cell_angle_gamma 106.84(2) _cell_volume 1468(1) _cell_formula_units_Z 2 _cell_measurement_reflns_used 10 _cell_measurement_theta_min 9 _cell_measurement_theta_max 11 _cell_measurement_temperature 294 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.09 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 2.01 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848.0 _exptl_absorpt_coefficient_mu 8.151 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(DeMeulenaer & Tompa, 1965)' _exptl_absorpt_correction_T_min 0.20 _exptl_absorpt_correction_T_max 0.46 # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 4282 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_theta_max 23 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 0 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 4076 _reflns_number_gt 2481 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.060 _refine_ls_wR_factor_ref 0.072 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2481 _refine_ls_number_parameters 167 _refine_ls_goodness_of_fit_ref 1.66 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.004 _refine_diff_density_max 1.89 _refine_diff_density_min -1.30 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy Br1 0.4204(1) -0.0701(1) 0.3519(1) 0.0625(4) Uani Br 1.0 Br2 1.0830(1) 0.0345(1) 0.3240(1) 0.0714(5) Uani Br 1.0 Br3 0.8126(2) 0.1585(2) -0.0528(1) 0.0831(5) Uani Br 1.0 Br4 0.2109(2) 0.2065(2) 0.1073(2) 0.1187(8) Uani Br 1.0 Br5 0.7926(2) 0.3957(2) 0.7552(1) 0.0952(6) Uani Br 1.0 Br6 1.3538(1) 0.5649(1) 0.5430(1) 0.0767(5) Uani Br 1.0 N1 0.7091(9) 0.1030(8) 0.1329(7) 0.049(1) Uani N 1.0 N2 0.8411(9) 0.2618(8) 0.5445(7) 0.049(1) Uani N 1.0 C1 0.7828(11) 0.0420(10) 0.2827(9) 0.045(1) Uani C 1.0 C2 0.6841(11) 0.0834(10) 0.2202(8) 0.045(1) Uani C 1.0 C3 0.5644(11) 0.1006(10) 0.2667(9) 0.046(1) Uani C 1.0 C4 0.5763(11) 0.0790(10) 0.3690(9) 0.046(1) Uani C 1.0 C5 0.7336(11) 0.0702(10) 0.3906(8) 0.045(1) Uani C 1.0 C6 0.8476(11) 0.1919(10) 0.4549(9) 0.046(1) Uani C 1.0 C7 0.9701(11) 0.2182(10) 0.4018(9) 0.046(1) Uani C 1.0 C8 0.9433(11) 0.1181(10) 0.3025(9) 0.047(1) Uani C 1.0 C9 0.6109(12) 0.1400(10) 0.0848(9) 0.052(1) Uani C 1.0 C10 0.6389(13) 0.1685(11) -0.0080(10) 0.060(1) Uani C 1.0 C11 0.5407(14) 0.2024(12) -0.0613(10) 0.067(2) Uani C 1.0 C12 0.4122(14) 0.2109(11) -0.0251(10) 0.065(2) Uani C 1.0 C13 0.3852(12) 0.1881(11) 0.0624(10) 0.058(2) Uani C 1.0 C14 0.4809(12) 0.1541(10) 0.1218(9) 0.052(1) Uani C 1.0 C15 0.4616(11) 0.1335(10) 0.2161(9) 0.049(1) Uani C 1.0 C16 0.9506(12) 0.3664(10) 0.5885(9) 0.051(2) Uani C 1.0 C17 0.9498(13) 0.4456(11) 0.6889(9) 0.058(2) Uani C 1.0 C18 1.0542(13) 0.5508(11) 0.7373(10) 0.063(2) Uani C 1.0 C19 1.1776(13) 0.5854(11) 0.6921(10) 0.061(2) Uani C 1.0 C20 1.1843(12) 0.5158(11) 0.5989(10) 0.056(2) Uani C 1.0 C21 1.0766(11) 0.4041(10) 0.5452(9) 0.051(2) Uani C 1.0 C22 1.0801(11) 0.3233(10) 0.4459(9) 0.049(1) Uani C 1.0 C1Px 0.3371(8) 0.3168(7) 0.6810(8) 0.066(4) Uani C 1.0 C2Px 0.4233(10) 0.4223(8) 0.7593(8) 0.076(5) Uani C 1.0 C3Px 0.3761(11) 0.4650(8) 0.8509(7) 0.084(6) Uani C 1.0 C4Px 0.2414(9) 0.4035(7) 0.8666(9) 0.082(4) Uani C 1.0 C5Px 0.1552(10) 0.2980(9) 0.7883(8) 0.076(4) Uani C 1.0 C6Px 0.2023(9) 0.2552(8) 0.6967(7) 0.069(4) Uani C 1.0 C7Px 0.3888(11) 0.2699(9) 0.5807(9) 0.081(5) Uani C 1.0 C8Px 0.1897(13) 0.4503(10) 0.9669(10) 0.113(8) Uani C 1.0 HC1 0.7667 -0.0435 0.2486 0.047 Uani H 1.0 HC4 0.5675 0.1457 0.4271 0.048 Uani H 1.0 HC5 0.7362 0.0109 0.4248 0.047 Uani H 1.0 HC8 0.9598 0.1473 0.2425 0.049 Uani H 1.0 HC11 0.5605 0.2212 -0.1261 0.076 Uani H 1.0 HC12 0.3395 0.2343 -0.0652 0.072 Uani H 1.0 HC15 0.3736 0.1428 0.2462 0.051 Uani H 1.0 HC18 1.0456 0.6052 0.8053 0.070 Uani H 1.0 HC19 1.2599 0.6624 0.7303 0.066 Uani H 1.0 HC22 1.1636 0.3451 0.4098 0.052 Uani H 1.0 HC2Px 0.5213 0.4684 0.7496 0.094 Uani H 1.0 HC3Px 0.4405 0.5417 0.9066 0.108 Uani H 1.0 HC5Px 0.0571 0.2519 0.7980 0.094 Uani H 1.0 HC6Px 0.1380 0.1786 0.6410 0.083 Uani H 1.0 H1C7Px 0.3376 0.2875 0.5221 0.088 Uani H 1.0 H2C7Px 0.4992 0.3084 0.5932 0.094 Uani H 1.0 H3C7Px 0.3636 0.1829 0.5605 0.090 Uani H 1.0 H1C8Px 0.2535 0.4458 1.0282 0.126 Uani H 1.0 H2C8Px 0.1981 0.5341 0.9800 0.130 Uani H 1.0 H3C8Px 0.0834 0.4021 0.9588 0.124 Uani H 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol Br1 0.0488(7) 0.0653(9) 0.0705(9) 0.0074(6) 0.0141(6) 0.0312(7) Br Br2 0.0498(7) 0.064(1) 0.098(1) 0.0286(7) 0.0183(7) 0.0168(8) Br Br3 0.0654(9) 0.118(1) 0.071(1) 0.0239(8) 0.0281(7) 0.0424(9) Br Br4 0.089(1) 0.176(2) 0.166(2) 0.090(1) 0.060(1) 0.109(2) Br Br5 0.076(1) 0.106(1) 0.074(1) 0.0123(9) 0.0339(8) 0.0025(9) Br Br6 0.0530(8) 0.0564(9) 0.116(1) 0.0091(6) 0.0242(7) 0.0312(9) Br N1 0.045(2) 0.049(2) 0.054(2) 0.015(1) 0.014(1) 0.018(1) N N2 0.044(2) 0.047(2) 0.054(2) 0.016(1) 0.013(1) 0.015(1) N C1 0.037(2) 0.043(2) 0.055(2) 0.014(1) 0.013(1) 0.016(1) C C2 0.039(2) 0.044(2) 0.054(2) 0.014(1) 0.013(1) 0.016(1) C C3 0.037(2) 0.043(2) 0.057(2) 0.014(1) 0.012(1) 0.017(1) C C4 0.038(2) 0.045(2) 0.057(2) 0.014(1) 0.015(1) 0.018(2) C C5 0.038(2) 0.044(2) 0.054(2) 0.014(1) 0.013(1) 0.018(1) C C6 0.039(1) 0.044(2) 0.054(2) 0.014(1) 0.012(1) 0.016(1) C C7 0.037(2) 0.043(2) 0.058(2) 0.013(1) 0.012(1) 0.017(1) C C8 0.037(2) 0.045(2) 0.058(2) 0.014(1) 0.015(1) 0.017(1) C C9 0.049(2) 0.050(2) 0.056(2) 0.015(1) 0.010(1) 0.020(2) C C10 0.063(3) 0.060(3) 0.058(2) 0.017(3) 0.011(2) 0.024(2) C C11 0.072(4) 0.063(4) 0.063(3) 0.017(4) 0.004(2) 0.028(3) C C12 0.065(4) 0.056(3) 0.070(3) 0.016(3) -0.003(2) 0.025(3) C C13 0.051(3) 0.049(3) 0.070(3) 0.015(3) 0.000(2) 0.021(2) C C14 0.045(2) 0.046(2) 0.062(2) 0.014(2) 0.006(1) 0.019(2) C C15 0.038(2) 0.044(2) 0.062(2) 0.014(2) 0.009(1) 0.017(1) C C16 0.046(2) 0.047(2) 0.057(2) 0.016(1) 0.009(1) 0.013(1) C C17 0.056(3) 0.053(2) 0.058(3) 0.020(2) 0.009(2) 0.010(2) C C18 0.060(4) 0.053(2) 0.064(3) 0.020(2) 0.003(2) 0.007(2) C C19 0.052(3) 0.047(2) 0.072(4) 0.016(2) -0.001(3) 0.010(2) C C20 0.044(2) 0.044(2) 0.072(4) 0.014(2) 0.003(2) 0.014(2) C C21 0.041(2) 0.044(2) 0.063(3) 0.014(1) 0.007(2) 0.015(1) C C22 0.037(2) 0.044(2) 0.064(2) 0.013(1) 0.011(1) 0.018(1) C C1Px 0.064(6) 0.063(5) 0.081(5) 0.028(5) 0.014(4) 0.034(4) C C2Px 0.068(6) 0.068(7) 0.091(5) 0.020(6) 0.012(3) 0.033(4) C C3Px 0.090(8) 0.070(8) 0.087(6) 0.025(5) 0.011(4) 0.025(5) C C4Px 0.093(7) 0.081(6) 0.085(6) 0.042(5) 0.024(4) 0.035(4) C C5Px 0.072(7) 0.078(5) 0.093(6) 0.032(4) 0.024(4) 0.043(4) C C6Px 0.065(7) 0.063(5) 0.085(5) 0.024(4) 0.013(4) 0.034(4) C C7Px 0.087(6) 0.084(6) 0.090(5) 0.043(6) 0.028(5) 0.041(4) C C8Px 0.147(9) 0.121(9) 0.098(7) 0.072(9) 0.049(7) 0.042(7) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C4 1.971(11) 1_555 1_555 no Br2 C8 1.981(11) 1_555 1_555 no Br3 C10 1.863(12) 1_555 1_555 no Br4 C13 1.897(12) 1_555 1_555 no Br5 C17 1.892(12) 1_555 1_555 no Br6 C20 1.894(12) 1_555 1_555 no N1 C2 1.314(13) 1_555 1_555 no N1 C9 1.353(14) 1_555 1_555 no N2 C6 1.291(13) 1_555 1_555 no N2 C16 1.338(13) 1_555 1_555 no C1 C2 1.503(15) 1_555 1_555 no C1 C5 1.558(14) 1_555 1_555 no C1 C8 1.504(14) 1_555 1_555 no C2 C3 1.412(14) 1_555 1_555 no C3 C4 1.490(15) 1_555 1_555 no C3 C15 1.368(15) 1_555 1_555 no C4 C5 1.546(14) 1_555 1_555 no C5 C6 1.527(14) 1_555 1_555 no C6 C7 1.456(14) 1_555 1_555 no C7 C8 1.481(14) 1_555 1_555 no C7 C22 1.346(14) 1_555 1_555 no C9 C10 1.441(16) 1_555 1_555 no C9 C14 1.435(15) 1_555 1_555 no C10 C11 1.364(16) 1_555 1_555 no C11 C12 1.400(17) 1_555 1_555 no C12 C13 1.337(17) 1_555 1_555 no C13 C14 1.394(16) 1_555 1_555 no C14 C15 1.401(15) 1_555 1_555 no C16 C17 1.430(15) 1_555 1_555 no C16 C21 1.426(15) 1_555 1_555 no C17 C18 1.328(16) 1_555 1_555 no C18 C19 1.414(17) 1_555 1_555 no C19 C20 1.326(16) 1_555 1_555 no C20 C21 1.401(15) 1_555 1_555 no C21 C22 1.436(15) 1_555 1_555 no C1Px C2Px 1.380(8) 1_555 1_555 no C1Px C6Px 1.380(8) 1_555 1_555 no C1Px C7Px 1.512(14) 1_555 1_555 no C2Px C3Px 1.380(12) 1_555 1_555 no C3Px C4Px 1.380(8) 1_555 1_555 no C4Px C5Px 1.380(8) 1_555 1_555 no C4Px C8Px 1.512(14) 1_555 1_555 no C5Px C6Px 1.380(12) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C9 116.8(9) 1_555 1_555 1_555 no C6 N2 C16 117.7(9) 1_555 1_555 1_555 no C2 C1 C5 101.3(8) 1_555 1_555 1_555 no C2 C1 C8 109.8(9) 1_555 1_555 1_555 no C5 C1 C8 107.8(8) 1_555 1_555 1_555 no N1 C2 C1 123.2(9) 1_555 1_555 1_555 no N1 C2 C3 124.2(10) 1_555 1_555 1_555 no C1 C2 C3 112.7(10) 1_555 1_555 1_555 no C2 C3 C4 109.9(9) 1_555 1_555 1_555 no C2 C3 C15 119.2(11) 1_555 1_555 1_555 no C4 C3 C15 130.9(10) 1_555 1_555 1_555 no Br1 C4 C3 109.5(7) 1_555 1_555 1_555 no Br1 C4 C5 110.9(7) 1_555 1_555 1_555 no C3 C4 C5 104.0(8) 1_555 1_555 1_555 no C1 C5 C4 107.4(8) 1_555 1_555 1_555 no C1 C5 C6 102.1(8) 1_555 1_555 1_555 no C4 C5 C6 109.8(9) 1_555 1_555 1_555 no N2 C6 C5 126.2(9) 1_555 1_555 1_555 no N2 C6 C7 123.8(10) 1_555 1_555 1_555 no C5 C6 C7 110.0(9) 1_555 1_555 1_555 no C6 C7 C8 109.5(9) 1_555 1_555 1_555 no C6 C7 C22 118.5(10) 1_555 1_555 1_555 no C8 C7 C22 132.0(10) 1_555 1_555 1_555 no Br2 C8 C1 112.2(8) 1_555 1_555 1_555 no Br2 C8 C7 108.3(7) 1_555 1_555 1_555 no C1 C8 C7 105.8(8) 1_555 1_555 1_555 no N1 C9 C10 118.4(10) 1_555 1_555 1_555 no N1 C9 C14 123.7(11) 1_555 1_555 1_555 no C10 C9 C14 117.8(11) 1_555 1_555 1_555 no Br3 C10 C9 118.4(9) 1_555 1_555 1_555 no Br3 C10 C11 120.9(10) 1_555 1_555 1_555 no C9 C10 C11 120.7(12) 1_555 1_555 1_555 no C10 C11 C12 119.8(12) 1_555 1_555 1_555 no C11 C12 C13 120.9(12) 1_555 1_555 1_555 no Br4 C13 C12 117.7(9) 1_555 1_555 1_555 no Br4 C13 C14 119.6(10) 1_555 1_555 1_555 no C12 C13 C14 122.7(12) 1_555 1_555 1_555 no C9 C14 C13 118.0(11) 1_555 1_555 1_555 no C9 C14 C15 116.7(10) 1_555 1_555 1_555 no C13 C14 C15 125.3(11) 1_555 1_555 1_555 no C3 C15 C14 119.3(10) 1_555 1_555 1_555 no N2 C16 C17 119.7(10) 1_555 1_555 1_555 no N2 C16 C21 124.5(10) 1_555 1_555 1_555 no C17 C16 C21 115.8(10) 1_555 1_555 1_555 no Br5 C17 C16 117.7(9) 1_555 1_555 1_555 no Br5 C17 C18 119.2(9) 1_555 1_555 1_555 no C16 C17 C18 123.1(12) 1_555 1_555 1_555 no C17 C18 C19 119.6(11) 1_555 1_555 1_555 no C18 C19 C20 120.0(11) 1_555 1_555 1_555 no Br6 C20 C19 118.3(9) 1_555 1_555 1_555 no Br6 C20 C21 119.3(9) 1_555 1_555 1_555 no C19 C20 C21 122.2(11) 1_555 1_555 1_555 no C16 C21 C20 119.2(11) 1_555 1_555 1_555 no C16 C21 C22 116.0(10) 1_555 1_555 1_555 no C20 C21 C22 124.8(10) 1_555 1_555 1_555 no C7 C22 C21 119.4(10) 1_555 1_555 1_555 no C2Px C1Px C6Px 118.2(10) 1_555 1_555 1_555 no C2Px C1Px C7Px 120.9(5) 1_555 1_555 1_555 no C6Px C1Px C7Px 120.9(5) 1_555 1_555 1_555 no C1Px C2Px C3Px 120.9(5) 1_555 1_555 1_555 no C2Px C3Px C4Px 120.9(5) 1_555 1_555 1_555 no C3Px C4Px C5Px 118.2(10) 1_555 1_555 1_555 no C3Px C4Px C8Px 120.9(5) 1_555 1_555 1_555 no C5Px C4Px C8Px 120.9(5) 1_555 1_555 1_555 no C4Px C5Px C6Px 120.9(5) 1_555 1_555 1_555 no C1Px C6Px C5Px 120.9(5) 1_555 1_555 1_555 no data_DRB268_C22H10Br6N2 _database_code_CSD 201128 _audit_creation_method 'RAELSPUB and manual entry' # TEXT _publ_section_abstract ? _publ_section_comment ? _publ_section_acknowledgements ? _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. De Meulenaer, J. and Tompa, H. Acta Cryst., 1965, 19, 1014. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee, U.S.A., 1976. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1989. ; _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ? _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'RAELS, (Rae, 1989)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C22 H10 Br6 N2' _chemical_formula_sum 'C22 H10 Br6 N2' _chemical_formula_iupac ? _chemical_formula_weight 781.8 # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 9.212(5) _cell_length_b 15.384(6) _cell_length_c 17.735(7) _cell_angle_alpha 90 _cell_angle_beta 111.75(2) _cell_angle_gamma 90 _cell_volume 2334(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 10 _cell_measurement_theta_min 10 _cell_measurement_theta_max 11 _cell_measurement_temperature 294 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 2.22 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464.0 _exptl_absorpt_coefficient_mu 10.233 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(DeMeulenaer & Tompa, 1965)' _exptl_absorpt_correction_T_min 0.18 _exptl_absorpt_correction_T_max 0.37 # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 3908 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_theta_max 24 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 0 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 3656 _reflns_number_gt 1727 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.062 _refine_ls_wR_factor_ref 0.068 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1727 _refine_ls_number_parameters 141 _refine_ls_goodness_of_fit_ref 1.91 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.003 _refine_diff_density_max 2.37 _refine_diff_density_min -2.08 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy Br1 0.7653(3) 0.8557(2) 0.8073(1) 0.1012(8) Uani Br 1.0 Br2 0.1447(2) 0.6977(1) 0.6899(1) 0.0734(6) Uani Br 1.0 Br3 0.1780(2) 0.9246(1) 0.3767(1) 0.0739(6) Uani Br 1.0 Br4 0.9372(2) 0.8813(1) 0.4968(1) 0.0843(7) Uani Br 1.0 Br5 0.8725(2) 0.4472(1) 0.7442(2) 0.1022(8) Uani Br 1.0 Br6 0.1833(2) 0.3983(1) 0.4577(1) 0.0894(7) Uani Br 1.0 N1 0.3930(13) 0.8521(7) 0.5369(8) 0.048(2) Uani N 1.0 N2 0.6117(14) 0.5772(8) 0.6947(8) 0.054(2) Uani N 1.0 C1 0.4036(18) 0.7826(9) 0.6646(9) 0.051(2) Uani C 1.0 C2 0.4745(17) 0.8189(9) 0.6083(9) 0.047(2) Uani C 1.0 C3 0.6401(17) 0.8087(9) 0.6410(9) 0.047(2) Uani C 1.0 C4 0.6859(17) 0.7675(9) 0.7219(9) 0.052(2) Uani C 1.0 C5 0.5355(17) 0.7261(9) 0.7219(9) 0.052(2) Uani C 1.0 C6 0.5077(17) 0.6399(9) 0.6790(9) 0.051(2) Uani C 1.0 C7 0.3551(17) 0.6358(9) 0.6194(9) 0.051(2) Uani C 1.0 C8 0.2698(17) 0.7180(9) 0.6217(9) 0.053(3) Uani C 1.0 C9 0.4786(17) 0.8802(8) 0.4916(9) 0.048(2) Uani C 1.0 C10 0.3981(18) 0.9148(9) 0.4147(10) 0.052(2) Uani C 1.0 C11 0.4755(18) 0.9420(9) 0.3672(9) 0.056(2) Uani C 1.0 C12 0.6383(19) 0.9323(9) 0.3921(10) 0.055(2) Uani C 1.0 C13 0.7205(18) 0.8978(9) 0.4655(10) 0.052(2) Uani C 1.0 C14 0.6447(17) 0.8710(9) 0.5202(9) 0.047(2) Uani C 1.0 C15 0.7249(17) 0.8348(9) 0.5982(9) 0.048(2) Uani C 1.0 C16 0.5662(18) 0.5043(10) 0.6473(10) 0.057(3) Uani C 1.0 C17 0.6719(19) 0.4347(10) 0.6614(11) 0.066(4) Uani C 1.0 C18 0.6376(21) 0.3632(10) 0.6155(12) 0.074(6) Uani C 1.0 C19 0.4904(21) 0.3529(10) 0.5552(11) 0.074(6) Uani C 1.0 C20 0.3833(19) 0.4169(10) 0.5412(11) 0.065(5) Uani C 1.0 C21 0.4144(18) 0.4956(9) 0.5843(10) 0.057(3) Uani C 1.0 C22 0.3068(17) 0.5628(9) 0.5717(10) 0.054(3) Uani C 1.0 HC1 0.3707 0.8292 0.6943 0.057 Uani H 1.0 HC4 0.7671 0.7219 0.7285 0.054 Uani H 1.0 HC5 0.5324 0.7221 0.7776 0.058 Uani H 1.0 HC8 0.2033 0.7382 0.5659 0.054 Uani H 1.0 HC11 0.4158 0.9695 0.3135 0.062 Uani H 1.0 HC12 0.6930 0.9508 0.3554 0.061 Uani H 1.0 HC15 0.8413 0.8291 0.6204 0.051 Uani H 1.0 HC18 0.7183 0.3167 0.6245 0.084 Uani H 1.0 HC19 0.4639 0.2982 0.5224 0.083 Uani H 1.0 HC22 0.1988 0.5583 0.5297 0.057 Uani H 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol Br1 0.117(2) 0.106(2) 0.086(2) -0.051(1) 0.043(1) -0.030(1) Br Br2 0.058(1) 0.088(1) 0.086(2) -0.007(1) 0.041(1) 0.005(1) Br Br3 0.066(1) 0.084(1) 0.076(1) 0.013(1) 0.031(1) 0.004(1) Br Br4 0.066(1) 0.085(1) 0.124(2) -0.003(1) 0.061(1) 0.005(1) Br Br5 0.062(1) 0.080(2) 0.139(2) 0.015(1) 0.008(1) -0.004(1) Br Br6 0.079(1) 0.092(2) 0.092(2) -0.028(1) 0.025(1) -0.028(1) Br N1 0.055(3) 0.042(2) 0.057(3) -0.002(2) 0.032(2) -0.004(2) N N2 0.056(3) 0.045(2) 0.066(4) -0.004(2) 0.028(3) 0.002(3) N C1 0.062(3) 0.046(2) 0.059(4) -0.003(2) 0.038(3) -0.004(2) C C2 0.056(3) 0.042(2) 0.054(3) -0.002(2) 0.033(3) -0.005(2) C C3 0.056(3) 0.042(2) 0.053(4) -0.003(2) 0.030(3) -0.005(2) C C4 0.062(3) 0.047(2) 0.054(4) -0.007(2) 0.028(3) -0.002(2) C C5 0.063(4) 0.049(2) 0.054(4) -0.007(2) 0.032(3) -0.003(2) C C6 0.056(3) 0.045(2) 0.058(3) -0.004(2) 0.029(3) -0.001(2) C C7 0.055(3) 0.045(2) 0.059(4) -0.004(2) 0.029(3) -0.001(2) C C8 0.057(3) 0.047(2) 0.064(5) -0.002(2) 0.035(3) 0.001(3) C C9 0.056(3) 0.042(2) 0.053(3) -0.003(2) 0.030(2) -0.004(2) C C10 0.060(3) 0.047(2) 0.056(3) -0.007(2) 0.027(3) -0.001(2) C C11 0.067(5) 0.052(3) 0.054(3) -0.010(3) 0.029(3) -0.002(2) C C12 0.069(5) 0.052(3) 0.057(3) -0.007(3) 0.037(4) -0.004(3) C C13 0.062(3) 0.047(3) 0.059(4) -0.003(2) 0.038(4) -0.004(2) C C14 0.056(3) 0.042(2) 0.054(3) -0.002(2) 0.032(3) -0.005(2) C C15 0.055(3) 0.042(2) 0.056(3) -0.002(2) 0.031(3) -0.004(2) C C16 0.059(3) 0.043(2) 0.074(4) -0.003(2) 0.031(3) 0.001(3) C C17 0.064(4) 0.043(3) 0.096(7) 0.000(2) 0.036(4) 0.005(3) C C18 0.078(7) 0.041(3) 0.112(9) 0.001(3) 0.045(7) 0.001(3) C C19 0.087(9) 0.041(3) 0.100(9) -0.005(2) 0.043(7) -0.006(2) C C20 0.078(6) 0.042(3) 0.080(7) -0.008(3) 0.033(5) -0.005(3) C C21 0.064(3) 0.042(2) 0.069(5) -0.005(2) 0.029(3) -0.002(2) C C22 0.059(3) 0.044(2) 0.062(5) -0.006(2) 0.027(3) 0.000(3) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C4 1.961(15) 1_555 1_555 no Br2 C8 1.981(14) 1_555 1_555 no Br3 C10 1.891(15) 1_555 1_555 no Br4 C13 1.880(15) 1_555 1_555 no Br5 C17 1.896(17) 1_555 1_555 no Br6 C20 1.910(17) 1_555 1_555 no N1 C2 1.313(17) 1_555 1_555 no N1 C9 1.387(17) 1_555 1_555 no N2 C6 1.315(16) 1_555 1_555 no N2 C16 1.370(17) 1_555 1_555 no C1 C2 1.489(19) 1_555 1_555 no C1 C5 1.533(19) 1_555 1_555 no C1 C8 1.547(19) 1_555 1_555 no C2 C3 1.425(19) 1_555 1_555 no C3 C4 1.478(19) 1_555 1_555 no C3 C15 1.339(18) 1_555 1_555 no C4 C5 1.526(18) 1_555 1_555 no C5 C6 1.502(19) 1_555 1_555 no C6 C7 1.413(19) 1_555 1_555 no C7 C8 1.497(18) 1_555 1_555 no C7 C22 1.377(19) 1_555 1_555 no C9 C10 1.394(19) 1_555 1_555 no C9 C14 1.430(19) 1_555 1_555 no C10 C11 1.356(18) 1_555 1_555 no C11 C12 1.405(20) 1_555 1_555 no C12 C13 1.350(20) 1_555 1_555 no C13 C14 1.449(18) 1_555 1_555 no C14 C15 1.418(18) 1_555 1_555 no C16 C17 1.406(19) 1_555 1_555 no C16 C21 1.436(19) 1_555 1_555 no C17 C18 1.336(21) 1_555 1_555 no C18 C19 1.389(22) 1_555 1_555 no C19 C20 1.351(21) 1_555 1_555 no C20 C21 1.404(20) 1_555 1_555 no C21 C22 1.392(19) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C9 115.8(12) 1_555 1_555 1_555 no C6 N2 C16 116.0(13) 1_555 1_555 1_555 no C2 C1 C5 102.7(12) 1_555 1_555 1_555 no C2 C1 C8 112.2(12) 1_555 1_555 1_555 no C5 C1 C8 104.6(11) 1_555 1_555 1_555 no N1 C2 C1 123.8(14) 1_555 1_555 1_555 no N1 C2 C3 125.4(13) 1_555 1_555 1_555 no C1 C2 C3 110.8(14) 1_555 1_555 1_555 no C2 C3 C4 108.7(13) 1_555 1_555 1_555 no C2 C3 C15 119.8(14) 1_555 1_555 1_555 no C4 C3 C15 131.5(14) 1_555 1_555 1_555 no Br1 C4 C3 110.1(10) 1_555 1_555 1_555 no Br1 C4 C5 111.6(10) 1_555 1_555 1_555 no C3 C4 C5 104.3(12) 1_555 1_555 1_555 no C1 C5 C4 105.0(12) 1_555 1_555 1_555 no C1 C5 C6 102.8(12) 1_555 1_555 1_555 no C4 C5 C6 110.7(12) 1_555 1_555 1_555 no N2 C6 C5 124.5(14) 1_555 1_555 1_555 no N2 C6 C7 124.8(14) 1_555 1_555 1_555 no C5 C6 C7 110.7(13) 1_555 1_555 1_555 no C6 C7 C8 109.2(13) 1_555 1_555 1_555 no C6 C7 C22 120.1(14) 1_555 1_555 1_555 no C8 C7 C22 130.7(14) 1_555 1_555 1_555 no Br2 C8 C1 109.8(10) 1_555 1_555 1_555 no Br2 C8 C7 108.3(10) 1_555 1_555 1_555 no C1 C8 C7 103.0(12) 1_555 1_555 1_555 no N1 C9 C10 118.4(14) 1_555 1_555 1_555 no N1 C9 C14 121.8(14) 1_555 1_555 1_555 no C10 C9 C14 119.7(13) 1_555 1_555 1_555 no Br3 C10 C9 119.4(11) 1_555 1_555 1_555 no Br3 C10 C11 119.7(12) 1_555 1_555 1_555 no C9 C10 C11 120.9(15) 1_555 1_555 1_555 no C10 C11 C12 121.2(15) 1_555 1_555 1_555 no C11 C12 C13 119.8(14) 1_555 1_555 1_555 no Br4 C13 C12 119.5(11) 1_555 1_555 1_555 no Br4 C13 C14 119.1(12) 1_555 1_555 1_555 no C12 C13 C14 121.4(14) 1_555 1_555 1_555 no C9 C14 C13 116.9(14) 1_555 1_555 1_555 no C9 C14 C15 119.2(13) 1_555 1_555 1_555 no C13 C14 C15 123.9(14) 1_555 1_555 1_555 no C3 C15 C14 118.0(14) 1_555 1_555 1_555 no N2 C16 C17 118.6(15) 1_555 1_555 1_555 no N2 C16 C21 122.8(14) 1_555 1_555 1_555 no C17 C16 C21 118.6(15) 1_555 1_555 1_555 no Br5 C17 C16 118.2(12) 1_555 1_555 1_555 no Br5 C17 C18 119.9(13) 1_555 1_555 1_555 no C16 C17 C18 121.8(17) 1_555 1_555 1_555 no C17 C18 C19 120.4(16) 1_555 1_555 1_555 no C18 C19 C20 119.8(16) 1_555 1_555 1_555 no Br6 C20 C19 117.6(13) 1_555 1_555 1_555 no Br6 C20 C21 119.7(12) 1_555 1_555 1_555 no C19 C20 C21 122.7(16) 1_555 1_555 1_555 no C16 C21 C20 116.6(15) 1_555 1_555 1_555 no C16 C21 C22 119.1(14) 1_555 1_555 1_555 no C20 C21 C22 124.3(15) 1_555 1_555 1_555 no C7 C22 C21 117.2(14) 1_555 1_555 1_555 no data_DRB261_C22H10Br6N2,C7H8 _database_code_CSD 201129 _audit_creation_method 'RAELSPUB and manual entry' # TEXT _publ_section_abstract ? _publ_section_comment ? _publ_section_acknowledgements ? _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. De Meulenaer, J. and Tompa, H. Acta Cryst., 1965, 19, 1014. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee, U.S.A., 1976. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1989. ; _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ? _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'RAELS, (Rae, 1989)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C22 H10 Br6 N2,C7 H8' _chemical_formula_sum 'C29 H18 Br6 N2' _chemical_formula_iupac ? _chemical_formula_weight 873.9 # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 9.384(5) _cell_length_b 12.901(6) _cell_length_c 13.415(7) _cell_angle_alpha 103.57(2) _cell_angle_beta 100.24(3) _cell_angle_gamma 109.04(2) _cell_volume 1434(1) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 16 _cell_measurement_temperature 294 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 2.02 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832.0 _exptl_absorpt_coefficient_mu 8.340 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(DeMeulenaer & Tompa, 1965)' _exptl_absorpt_correction_T_min 0.15 _exptl_absorpt_correction_T_max 0.43 # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 5254 _diffrn_reflns_av_R_equivalents 0.065 _diffrn_reflns_theta_max 25 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 0 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 5021 _reflns_number_gt 2545 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.079 _refine_ls_wR_factor_ref 0.095 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2545 _refine_ls_number_parameters 168 _refine_ls_goodness_of_fit_ref 1.69 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.002 _refine_diff_density_max 1.80 _refine_diff_density_min -1.64 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy Br1 0.4439(2) -0.0878(1) 0.3549(1) 0.0758(6) Uani Br 1.0 Br2 1.1330(2) 0.0656(2) 0.3652(1) 0.0839(6) Uani Br 1.0 Br3 0.8241(2) 0.1695(2) -0.0479(1) 0.0882(6) Uani Br 1.0 Br4 0.1933(2) 0.1757(2) 0.0884(2) 0.1142(8) Uani Br 1.0 Br5 0.7765(2) 0.4007(2) 0.7318(2) 0.1019(7) Uani Br 1.0 Br6 1.3944(2) 0.5907(2) 0.5645(2) 0.0966(7) Uani Br 1.0 N1 0.7284(12) 0.1086(9) 0.1397(8) 0.053(2) Uani N 1.0 N2 0.8547(13) 0.2673(10) 0.5450(8) 0.058(3) Uani N 1.0 C1 0.8155(16) 0.0549(12) 0.3001(10) 0.057(3) Uani C 1.0 C2 0.7034(15) 0.0855(12) 0.2281(10) 0.053(2) Uani C 1.0 C3 0.5769(15) 0.0905(12) 0.2681(10) 0.055(3) Uani C 1.0 C4 0.5927(16) 0.0686(12) 0.3737(10) 0.058(3) Uani C 1.0 C5 0.7660(16) 0.0797(12) 0.4071(10) 0.058(3) Uani C 1.0 C6 0.8730(16) 0.2019(12) 0.4647(10) 0.056(3) Uani C 1.0 C7 1.0015(15) 0.2365(13) 0.4205(10) 0.057(2) Uani C 1.0 C8 0.9837(15) 0.1396(12) 0.3267(10) 0.058(3) Uani C 1.0 C9 0.6186(15) 0.1380(12) 0.0856(10) 0.054(2) Uani C 1.0 C10 0.6451(16) 0.1689(12) -0.0074(10) 0.057(2) Uani C 1.0 C11 0.5347(16) 0.1996(12) -0.0672(10) 0.062(2) Uani C 1.0 C12 0.4045(17) 0.2016(13) -0.0368(10) 0.065(2) Uani C 1.0 C13 0.3753(15) 0.1722(12) 0.0528(11) 0.063(2) Uani C 1.0 C14 0.4816(15) 0.1396(12) 0.1151(10) 0.057(2) Uani C 1.0 C15 0.4634(15) 0.1153(12) 0.2107(10) 0.057(2) Uani C 1.0 C16 0.9666(16) 0.3772(12) 0.5893(10) 0.059(2) Uani C 1.0 C17 0.9513(17) 0.4537(13) 0.6787(10) 0.063(2) Uani C 1.0 C18 1.0582(18) 0.5625(13) 0.7279(11) 0.067(2) Uani C 1.0 C19 1.1897(17) 0.6003(13) 0.6916(11) 0.068(3) Uani C 1.0 C20 1.2095(16) 0.5314(14) 0.6063(11) 0.066(3) Uani C 1.0 C21 1.1026(16) 0.4202(13) 0.5536(10) 0.060(2) Uani C 1.0 C22 1.1146(15) 0.3443(13) 0.4647(11) 0.059(2) Uani C 1.0 C1T 0.2206(16) 0.3999(12) 0.8636(14) 0.108(7) Uani C 1.0 C2T 0.3659(21) 0.4645(15) 0.8560(14) 0.122(6) Uani C 1.0 C3T 0.4192(21) 0.4181(19) 0.7730(17) 0.131(6) Uani C 1.0 C4T 0.3326(19) 0.3128(16) 0.7011(16) 0.121(8) Uani C 1.0 C5T 0.1909(22) 0.2505(14) 0.7092(13) 0.107(8) Uani C 1.0 C6T 0.1311(19) 0.2920(15) 0.7903(13) 0.105(8) Uani C 1.0 C7T 0.1568(25) 0.4495(19) 0.9561(18) 0.163(9) Uani C 1.0 HC1 0.8039 -0.0272 0.2716 0.060 Uani H 1.0 HC4 0.5741 0.1280 0.4268 0.059 Uani H 1.0 HC5 0.7793 0.0264 0.4482 0.063 Uani H 1.0 HC8 1.0019 0.1683 0.2651 0.057 Uani H 1.0 HC11 0.5524 0.2200 -0.1326 0.066 Uani H 1.0 HC12 0.3286 0.2247 -0.0798 0.072 Uani H 1.0 HC15 0.3695 0.1163 0.2358 0.062 Uani H 1.0 HC18 1.0430 0.6149 0.7894 0.071 Uani H 1.0 HC19 1.2713 0.6798 0.7291 0.074 Uani H 1.0 HC22 1.2053 0.3693 0.4344 0.063 Uani H 1.0 HC2T 0.4310 0.5425 0.9089 0.162 Uani H 1.0 HC3T 0.5241 0.4637 0.7664 0.183 Uani H 1.0 HC4T 0.3734 0.2811 0.6419 0.160 Uani H 1.0 HC5T 0.1276 0.1726 0.6555 0.136 Uani H 1.0 HC6T 0.0260 0.2451 0.7955 0.137 Uani H 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol Br1 0.100(1) 0.086(1) 0.068(1) 0.0383(9) 0.0436(9) 0.0534(9) Br Br2 0.090(1) 0.122(2) 0.090(1) 0.078(1) 0.0384(9) 0.061(1) Br Br3 0.074(1) 0.154(2) 0.075(1) 0.052(1) 0.0411(9) 0.077(1) Br Br4 0.095(1) 0.191(2) 0.137(2) 0.101(2) 0.058(1) 0.110(2) Br Br5 0.120(2) 0.118(2) 0.087(1) 0.051(1) 0.065(1) 0.034(1) Br Br6 0.083(1) 0.108(2) 0.123(2) 0.045(1) 0.044(1) 0.055(1) Br N1 0.065(5) 0.074(3) 0.049(2) 0.040(3) 0.028(2) 0.042(2) N N2 0.079(5) 0.077(2) 0.049(2) 0.047(2) 0.027(2) 0.043(2) N C1 0.075(7) 0.078(2) 0.050(3) 0.047(3) 0.030(3) 0.044(2) C C2 0.065(6) 0.074(2) 0.049(2) 0.040(2) 0.028(2) 0.042(2) C C3 0.063(5) 0.073(2) 0.053(2) 0.035(2) 0.029(2) 0.042(2) C C4 0.075(6) 0.074(2) 0.055(2) 0.039(2) 0.035(3) 0.043(2) C C5 0.080(7) 0.076(2) 0.050(2) 0.046(3) 0.032(3) 0.044(2) C C6 0.073(5) 0.078(2) 0.049(2) 0.047(2) 0.026(2) 0.043(2) C C7 0.065(5) 0.082(2) 0.054(3) 0.048(3) 0.023(2) 0.044(2) C C8 0.070(6) 0.084(3) 0.056(3) 0.051(4) 0.028(3) 0.046(2) C C9 0.063(5) 0.074(2) 0.049(2) 0.037(2) 0.023(2) 0.040(2) C C10 0.073(4) 0.075(2) 0.048(2) 0.040(3) 0.024(2) 0.041(2) C C11 0.078(4) 0.078(2) 0.049(2) 0.041(3) 0.017(2) 0.039(2) C C12 0.069(4) 0.083(3) 0.057(2) 0.038(3) 0.011(3) 0.039(2) C C13 0.058(4) 0.083(3) 0.061(3) 0.034(3) 0.014(2) 0.040(2) C C14 0.057(4) 0.076(2) 0.055(2) 0.033(3) 0.020(2) 0.040(2) C C15 0.056(5) 0.076(3) 0.059(2) 0.032(3) 0.026(2) 0.041(2) C C16 0.076(4) 0.079(2) 0.049(2) 0.046(2) 0.021(2) 0.042(2) C C17 0.089(4) 0.078(3) 0.048(2) 0.048(3) 0.023(2) 0.042(2) C C18 0.092(4) 0.080(3) 0.049(2) 0.047(3) 0.017(2) 0.040(2) C C19 0.079(3) 0.085(3) 0.055(2) 0.042(3) 0.009(3) 0.038(2) C C20 0.066(3) 0.087(3) 0.060(3) 0.042(2) 0.010(2) 0.040(2) C C21 0.066(4) 0.084(3) 0.054(2) 0.044(2) 0.015(2) 0.041(2) C C22 0.060(4) 0.086(3) 0.058(3) 0.046(2) 0.019(2) 0.043(2) C C1T 0.138(9) 0.135(9) 0.105(9) 0.092(7) 0.031(6) 0.082(6) C C2T 0.128(9) 0.130(9) 0.135(9) 0.073(9) 0.015(8) 0.074(7) C C3T 0.121(9) 0.154(9) 0.169(9) 0.078(8) 0.046(9) 0.099(9) C C4T 0.143(9) 0.156(9) 0.134(9) 0.103(9) 0.054(9) 0.095(7) C C5T 0.133(9) 0.125(9) 0.112(9) 0.086(8) 0.026(7) 0.078(7) C C6T 0.120(9) 0.127(9) 0.120(9) 0.079(8) 0.034(7) 0.090(7) C C7T 0.233(9) 0.204(9) 0.133(9) 0.147(9) 0.075(9) 0.090(9) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C4 1.970(13) 1_555 1_555 no Br2 C8 1.997(13) 1_555 1_555 no Br3 C10 1.853(13) 1_555 1_555 no Br4 C13 1.864(14) 1_555 1_555 no Br5 C17 1.891(14) 1_555 1_555 no Br6 C20 1.895(14) 1_555 1_555 no N1 C2 1.331(14) 1_555 1_555 no N1 C9 1.360(15) 1_555 1_555 no N2 C6 1.279(16) 1_555 1_555 no N2 C16 1.370(16) 1_555 1_555 no C1 C2 1.511(17) 1_555 1_555 no C1 C5 1.580(17) 1_555 1_555 no C1 C8 1.518(17) 1_555 1_555 no C2 C3 1.400(17) 1_555 1_555 no C3 C4 1.501(16) 1_555 1_555 no C3 C15 1.371(17) 1_555 1_555 no C4 C5 1.557(18) 1_555 1_555 no C5 C6 1.487(18) 1_555 1_555 no C6 C7 1.426(17) 1_555 1_555 no C7 C8 1.491(18) 1_555 1_555 no C7 C22 1.357(18) 1_555 1_555 no C9 C10 1.434(15) 1_555 1_555 no C9 C14 1.416(17) 1_555 1_555 no C10 C11 1.412(17) 1_555 1_555 no C11 C12 1.362(19) 1_555 1_555 no C12 C13 1.388(17) 1_555 1_555 no C13 C14 1.419(17) 1_555 1_555 no C14 C15 1.415(16) 1_555 1_555 no C16 C17 1.425(19) 1_555 1_555 no C16 C21 1.431(18) 1_555 1_555 no C17 C18 1.350(19) 1_555 1_555 no C18 C19 1.390(20) 1_555 1_555 no C19 C20 1.356(20) 1_555 1_555 no C20 C21 1.377(19) 1_555 1_555 no C21 C22 1.402(19) 1_555 1_555 no C1T C2T 1.383(18) 1_555 1_555 no C1T C6T 1.383(18) 1_555 1_555 no C1T C7T 1.565(31) 1_555 1_555 no C2T C3T 1.388(21) 1_555 1_555 no C3T C4T 1.350(19) 1_555 1_555 no C4T C5T 1.350(19) 1_555 1_555 no C5T C6T 1.388(21) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C9 115.3(11) 1_555 1_555 1_555 no C6 N2 C16 116.7(12) 1_555 1_555 1_555 no C2 C1 C5 101.5(10) 1_555 1_555 1_555 no C2 C1 C8 111.8(10) 1_555 1_555 1_555 no C5 C1 C8 105.4(11) 1_555 1_555 1_555 no N1 C2 C1 122.6(11) 1_555 1_555 1_555 no N1 C2 C3 125.3(12) 1_555 1_555 1_555 no C1 C2 C3 112.0(10) 1_555 1_555 1_555 no C2 C3 C4 111.0(11) 1_555 1_555 1_555 no C2 C3 C15 119.0(10) 1_555 1_555 1_555 no C4 C3 C15 130.0(11) 1_555 1_555 1_555 no Br1 C4 C3 109.5(9) 1_555 1_555 1_555 no Br1 C4 C5 111.7(9) 1_555 1_555 1_555 no C3 C4 C5 103.3(9) 1_555 1_555 1_555 no C1 C5 C4 105.9(10) 1_555 1_555 1_555 no C1 C5 C6 102.3(10) 1_555 1_555 1_555 no C4 C5 C6 110.9(11) 1_555 1_555 1_555 no N2 C6 C5 124.8(12) 1_555 1_555 1_555 no N2 C6 C7 124.1(14) 1_555 1_555 1_555 no C5 C6 C7 111.2(12) 1_555 1_555 1_555 no C6 C7 C8 109.7(12) 1_555 1_555 1_555 no C6 C7 C22 119.9(13) 1_555 1_555 1_555 no C8 C7 C22 130.5(12) 1_555 1_555 1_555 no Br2 C8 C1 110.4(9) 1_555 1_555 1_555 no Br2 C8 C7 110.2(8) 1_555 1_555 1_555 no C1 C8 C7 104.9(11) 1_555 1_555 1_555 no N1 C9 C10 117.0(11) 1_555 1_555 1_555 no N1 C9 C14 124.3(10) 1_555 1_555 1_555 no C10 C9 C14 118.7(11) 1_555 1_555 1_555 no Br3 C10 C9 120.0(10) 1_555 1_555 1_555 no Br3 C10 C11 120.4(9) 1_555 1_555 1_555 no C9 C10 C11 119.6(12) 1_555 1_555 1_555 no C10 C11 C12 120.8(11) 1_555 1_555 1_555 no C11 C12 C13 121.1(13) 1_555 1_555 1_555 no Br4 C13 C12 118.5(10) 1_555 1_555 1_555 no Br4 C13 C14 121.1(9) 1_555 1_555 1_555 no C12 C13 C14 120.4(13) 1_555 1_555 1_555 no C9 C14 C13 119.5(11) 1_555 1_555 1_555 no C9 C14 C15 117.3(11) 1_555 1_555 1_555 no C13 C14 C15 123.1(12) 1_555 1_555 1_555 no C3 C15 C14 118.6(12) 1_555 1_555 1_555 no N2 C16 C17 118.9(12) 1_555 1_555 1_555 no N2 C16 C21 124.1(13) 1_555 1_555 1_555 no C17 C16 C21 117.0(13) 1_555 1_555 1_555 no Br5 C17 C16 119.0(11) 1_555 1_555 1_555 no Br5 C17 C18 118.6(11) 1_555 1_555 1_555 no C16 C17 C18 122.4(13) 1_555 1_555 1_555 no C17 C18 C19 118.7(14) 1_555 1_555 1_555 no C18 C19 C20 121.3(14) 1_555 1_555 1_555 no Br6 C20 C19 117.9(12) 1_555 1_555 1_555 no Br6 C20 C21 120.4(12) 1_555 1_555 1_555 no C19 C20 C21 121.7(14) 1_555 1_555 1_555 no C16 C21 C20 118.9(14) 1_555 1_555 1_555 no C16 C21 C22 116.2(13) 1_555 1_555 1_555 no C20 C21 C22 124.9(13) 1_555 1_555 1_555 no C7 C22 C21 119.1(12) 1_555 1_555 1_555 no C2T C1T C6T 120.6(23) 1_555 1_555 1_555 no C2T C1T C7T 119.7(12) 1_555 1_555 1_555 no C6T C1T C7T 119.7(12) 1_555 1_555 1_555 no C1T C2T C3T 118.3(17) 1_555 1_555 1_555 no C2T C3T C4T 121.5(17) 1_555 1_555 1_555 no C3T C4T C5T 119.8(24) 1_555 1_555 1_555 no C4T C5T C6T 121.5(17) 1_555 1_555 1_555 no C1T C6T C5T 118.3(17) 1_555 1_555 1_555 no