#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/68/2206805.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2206805 loop_ _publ_author_name 'Westmoreland, Ian' 'Miyagi, Lowell' 'Que, Emily L.' _publ_section_title ; 1,5-Dibromo-2,4-bis[(2-bromophenyl)ethynyl]benzene ; _journal_coeditor_code TK6251 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2894 _journal_page_last o2895 _journal_paper_doi 10.1107/S1600536805025237 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C22 H10 Br4' _chemical_formula_moiety 'C22 H10 Br4' _chemical_formula_sum 'C22 H10 Br4' _chemical_formula_weight 593.94 _chemical_name_systematic ; 1,5-Dibromo-2,4-bis[(2-bromophenyl)ethynyl]benzene ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90 _cell_angle_beta 96.4810(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.0580(7) _cell_length_b 8.8663(6) _cell_length_c 21.870(2) _cell_measurement_reflns_used 2451 _cell_measurement_temperature 158 _cell_measurement_theta_max 24.6 _cell_measurement_theta_min 2.3 _cell_volume 1937.8(3) _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material TEXSAN _computing_structure_refinement 'TEXSAN (Molecular Structure Corporation and Rigaku, 1998)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _diffrn_measured_fraction_theta_full 0.97 _diffrn_measured_fraction_theta_max 0.97 _diffrn_measurement_device_type 'Bruker SMART 1000' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 8588 _diffrn_reflns_theta_full 24.7 _diffrn_reflns_theta_max 24.7 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 8.335 _exptl_absorpt_correction_T_max 0.435 _exptl_absorpt_correction_T_min 0.189 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 2.036 _exptl_crystal_density_method 'not measured' _exptl_crystal_description tablet _exptl_crystal_F_000 1128 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.36 _refine_diff_density_min -0.64 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.48 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 215 _refine_ls_number_reflns 2541 _refine_ls_R_factor_all 0.034 _refine_ls_R_factor_gt 0.034 _refine_ls_shift/su_max 0.000 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00022|Fo|^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.042 _refine_ls_wR_factor_ref 0.042 _reflns_number_gt 2541 _reflns_number_total 3198 _reflns_threshold_expression F^2^>3\s(F^2^) _cod_data_source_file tk6251.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2206805 _cod_database_fobs_code 2206805 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z 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_calc_flag _atom_site_occupancy _atom_site_type_symbol Br1 -0.01123(6) 0.60201(7) 0.56742(3) 0.0481(2) Uani d 1.00 Br Br2 -0.64754(5) 0.39476(6) 0.59125(2) 0.0347(2) Uani d 1.00 Br Br3 -0.65715(5) 0.03578(6) 0.37894(2) 0.03190(10) Uani d 1.00 Br Br4 -0.01904(6) -0.12230(7) 0.43676(3) 0.0446(2) Uani d 1.00 Br C1 -0.0766(5) 0.6509(5) 0.6425(2) 0.0260(10) Uani d 1.00 C C2 -0.0062(5) 0.7525(5) 0.6812(2) 0.0330(10) Uani d 1.00 C C3 -0.0512(5) 0.7875(6) 0.7371(2) 0.041(2) Uani d 1.00 C C4 -0.1652(5) 0.7200(5) 0.7540(2) 0.0350(10) Uani d 1.00 C C5 -0.2357(5) 0.6202(5) 0.7153(2) 0.0280(10) Uani d 1.00 C C6 -0.1934(4) 0.5828(5) 0.6584(2) 0.0230(10) Uani d 1.00 C C7 -0.2717(4) 0.4835(5) 0.6164(2) 0.0240(10) Uani d 1.00 C C8 -0.3387(4) 0.4061(5) 0.5811(2) 0.0240(10) Uani d 1.00 C C9 -0.4153(4) 0.3151(5) 0.5345(2) 0.0210(10) Uani d 1.00 C C10 -0.5535(4) 0.2994(5) 0.5321(2) 0.0220(10) Uani d 1.00 C C11 -0.6250(4) 0.2159(5) 0.4861(2) 0.0240(10) Uani d 1.00 C C12 -0.5573(4) 0.1463(5) 0.4427(2) 0.0210(10) Uani d 1.00 C C13 -0.4185(4) 0.1554(5) 0.4443(2) 0.0220(10) Uani d 1.00 C C14 -0.3498(4) 0.2406(5) 0.4907(2) 0.0240(10) Uani d 1.00 C C15 -0.3454(4) 0.0754(5) 0.4015(2) 0.0214(10) Uani d 1.00 C C16 -0.2798(4) 0.0087(5) 0.3684(2) 0.0250(10) Uani d 1.00 C C17 -0.1999(4) -0.0722(5) 0.3292(2) 0.0240(10) Uani d 1.00 C C18 -0.0809(5) -0.1408(5) 0.3526(2) 0.0280(10) Uani d 1.00 C C19 -0.0048(5) -0.2246(6) 0.3150(3) 0.039(2) Uani d 1.00 C C20 -0.0479(5) -0.2351(6) 0.2529(3) 0.039(2) Uani d 1.00 C C21 -0.1645(5) -0.1652(6) 0.2283(2) 0.036(2) Uani d 1.00 C C22 -0.2398(5) -0.0850(5) 0.2661(2) 0.0300(10) Uani d 1.00 C H(1) 0.0738 0.8013 0.6676 0.0410 Uiso calc 1.00 H H(2) 0.0023 0.8551 0.7647 0.0462 Uiso calc 1.00 H H(3) -0.1974 0.7481 0.7937 0.0442 Uiso calc 1.00 H H(4) -0.3166 0.5724 0.7264 0.0336 Uiso calc 1.00 H H(5) -0.7221 0.2093 0.4857 0.0302 Uiso calc 1.00 H H(6) -0.2531 0.2469 0.4926 0.0322 Uiso calc 1.00 H H(7) 0.0751 -0.2744 0.3322 0.0455 Uiso calc 1.00 H H(8) 0.0066 -0.2896 0.2262 0.0477 Uiso calc 1.00 H H(9) -0.1940 -0.1777 0.1852 0.0484 Uiso calc 1.00 H H(10) -0.3210 -0.0368 0.2473 0.0351 Uiso calc 1.00 H 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 Br1 0.0505(4) 0.0535(4) 0.0456(4) -0.0054(3) 0.0281(3) -0.0046(3) Br2 0.0384(3) 0.0347(3) 0.0335(3) 0.0030(2) 0.0154(2) -0.0062(2) Br3 0.0351(3) 0.0316(3) 0.0268(3) -0.0032(2) -0.0063(2) -0.0028(2) Br4 0.0393(3) 0.0597(4) 0.0328(3) 0.0082(3) -0.0042(2) 0.0026(3) C1 0.027(3) 0.022(3) 0.028(3) 0.002(2) 0.003(2) 0.002(2) C2 0.024(3) 0.027(3) 0.047(3) 0.000(2) -0.002(2) 0.001(3) C3 0.047(4) 0.028(3) 0.041(3) 0.003(3) -0.018(3) -0.005(2) C4 0.050(3) 0.029(3) 0.025(3) 0.003(3) 0.002(2) -0.005(2) C5 0.033(3) 0.026(3) 0.025(3) 0.003(2) 0.009(2) 0.003(2) C6 0.029(3) 0.019(2) 0.022(2) 0.007(2) 0.000(2) 0.002(2) C7 0.02(8) 0.0241 0.0241 0.0000 0.0027 0.0000 C8 0.02(8) 0.0241 0.0241 0.0000 0.0027 0.0000 C9 0.026(3) 0.018(2) 0.020(2) 0.001(2) 0.004(2) 0.002(2) C10 0.026(2) 0.021(2) 0.019(2) 0.000(2) 0.007(2) -0.001(2) C11 0.022(2) 0.023(3) 0.027(3) 0.004(2) 0.002(2) 0.006(2) C12 0.023(2) 0.018(2) 0.021(2) 0.000(2) -0.002(2) 0.001(2) C13 0.028(3) 0.019(2) 0.020(2) 0.002(2) 0.002(2) 0.004(2) C14 0.022(2) 0.026(3) 0.022(2) 0.000(2) 0.000(2) 0.004(2) C15 0.02(8) 0.0214 0.0214 0.0000 0.0024 0.0000 C16 0.03(8) 0.0253 0.0253 0.0000 0.0029 0.0000 C17 0.026(3) 0.018(2) 0.028(3) -0.002(2) 0.006(2) -0.002(2) C18 0.028(3) 0.027(3) 0.030(3) -0.005(2) 0.004(2) -0.001(2) C19 0.033(3) 0.032(3) 0.055(4) 0.004(2) 0.014(3) -0.003(3) C20 0.039(3) 0.033(3) 0.049(3) -0.008(3) 0.021(3) -0.018(3) C21 0.041(3) 0.038(3) 0.031(3) -0.010(3) 0.010(2) -0.014(2) C22 0.031(3) 0.029(3) 0.030(3) -0.002(2) 0.000(2) -0.005(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; Br Br -0.290 2.459 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag Br1 C1 C2 118.7(4) ? Br1 C1 C6 120.2(3) ? C2 C1 C6 121.1(4) ? C1 C2 C3 119.5(5) ? C2 C3 C4 120.2(4) ? C3 C4 C5 120.2(4) ? C4 C5 C6 121.0(4) ? C1 C6 C5 117.9(4) ? C1 C6 C7 121.3(4) ? C5 C6 C7 120.7(4) ? C6 C7 C8 177.7(5) ? C7 C8 C9 176.0(5) ? C8 C9 C10 122.1(4) ? C8 C9 C14 119.5(4) ? C10 C9 C14 118.4(4) ? Br2 C10 C9 120.3(3) ? Br2 C10 C11 118.6(3) ? C9 C10 C11 121.1(4) ? C10 C11 C12 119.0(4) ? Br3 C12 C11 118.5(3) ? Br3 C12 C13 119.6(3) ? C11 C12 C13 121.9(4) ? C12 C13 C14 117.7(4) ? C12 C13 C15 122.6(4) ? C14 C13 C15 119.7(4) ? C9 C14 C13 121.9(4) ? C13 C15 C16 176.8(5) ? C15 C16 C17 179.3(5) ? C16 C17 C18 121.2(4) ? C16 C17 C22 120.9(4) ? C18 C17 C22 117.9(4) ? Br4 C18 C17 119.9(4) ? Br4 C18 C19 118.5(4) ? C17 C18 C19 121.5(4) ? C18 C19 C20 118.8(5) ? C19 C20 C21 120.7(5) ? C20 C21 C22 119.8(5) ? C17 C22 C21 121.2(4) ? C1 C2 H(1) 118.767 no C3 C2 H(1) 121.681 no C2 C3 H(2) 118.354 no C4 C3 H(2) 121.305 no C3 C4 H(3) 119.361 no C5 C4 H(3) 120.350 no C4 C5 H(4) 121.230 no C6 C5 H(4) 117.782 no C10 C11 H(5) 118.322 no C12 C11 H(5) 122.649 no C9 C14 H(6) 119.634 no C13 C14 H(6) 118.484 no C18 C19 H(7) 120.540 no C20 C19 H(7) 120.679 no C19 C20 H(8) 119.256 no C21 C20 H(8) 119.988 no C20 C21 H(9) 118.998 no C22 C21 H(9) 121.081 no C17 C22 H(10) 121.087 no C21 C22 H(10) 117.753 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br1 C1 1.885(5) yes Br2 C10 1.887(4) yes Br3 C12 1.895(4) yes Br4 C18 1.882(5) yes C1 C2 1.377(6) no C1 C6 1.399(6) no C2 C3 1.386(7) no C3 C4 1.380(7) no C4 C5 1.367(7) no C5 C6 1.401(6) no C6 C7 1.438(6) yes C7 C8 1.189(6) yes C8 C9 1.449(6) yes C9 C10 1.391(6) no C9 C14 1.390(6) no C10 C11 1.384(6) no C11 C12 1.376(6) no C12 C13 1.395(6) no C13 C14 1.387(6) no C13 C15 1.437(6) yes C15 C16 1.193(6) yes C16 C17 1.433(6) yes C17 C18 1.387(6) no C17 C22 1.398(6) no C18 C19 1.398(7) no C19 C20 1.384(8) no C20 C21 1.381(7) no C21 C22 1.380(7) no C2 H(1) 0.988 no C3 H(2) 0.970 no C4 H(3) 0.991 no C5 H(4) 0.972 no C11 H(5) 0.978 no C14 H(6) 0.970 no C19 H(7) 0.955 no C20 H(8) 0.973 no C21 H(9) 0.962 no C22 H(10) 0.972 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 Br1 Br1 3.4890(10) 3_566 Br3 C4 3.545(5) 4_454 Br4 Br4 3.5020(10) 3_556 C2 C22 3.423(7) 4_555 C2 C17 3.533(6) 3_566 C2 C21 3.561(7) 4_555 C5 C20 3.486(7) 4_455 C7 C11 3.561(6) 3_466 C16 C21 3.589(6) 2_455 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Br1 C1 C2 C3 1_555 1_555 1_555 1_555 -178.7(4) no Br1 C1 C6 C5 1_555 1_555 1_555 1_555 178.5(3) no Br1 C1 C6 C7 1_555 1_555 1_555 1_555 -4.8(6) no Br2 C10 C9 C8 1_555 1_555 1_555 1_555 -1.2(6) no Br2 C10 C9 C14 1_555 1_555 1_555 1_555 178.8(3) no Br2 C10 C11 C12 1_555 1_555 1_555 1_555 179.9(3) no Br3 C12 C11 C10 1_555 1_555 1_555 1_555 -178.7(3) no Br3 C12 C13 C14 1_555 1_555 1_555 1_555 178.3(3) no Br3 C12 C13 C15 1_555 1_555 1_555 1_555 -4.3(6) no Br4 C18 C17 C16 1_555 1_555 1_555 1_555 -2.2(6) no Br4 C18 C17 C22 1_555 1_555 1_555 1_555 178.0(3) no Br4 C18 C19 C20 1_555 1_555 1_555 1_555 -178.3(4) no C1 C2 C3 C4 1_555 1_555 1_555 1_555 0.4(7) no C1 C6 C5 C4 1_555 1_555 1_555 1_555 0.0(7) no C1 C6 C7 C8 1_555 1_555 1_555 1_555 -89(12) no C2 C1 C6 C5 1_555 1_555 1_555 1_555 -0.7(6) no C2 C1 C6 C7 1_555 1_555 1_555 1_555 176.1(4) no C2 C3 C4 C5 1_555 1_555 1_555 1_555 -1.1(7) no C3 C2 C1 C6 1_555 1_555 1_555 1_555 0.5(7) no C3 C4 C5 C6 1_555 1_555 1_555 1_555 0.9(7) no C4 C5 C6 C7 1_555 1_555 1_555 1_555 -176.8(4) no C5 C6 C7 C8 1_555 1_555 1_555 1_555 87(12) no C6 C7 C8 C9 1_555 1_555 1_555 1_555 76(15) no C7 C8 C9 C10 1_555 1_555 1_555 1_555 -138(6) no C7 C8 C9 C14 1_555 1_555 1_555 1_555 41(6) no C8 C9 C10 C11 1_555 1_555 1_555 1_555 177.9(4) no C8 C9 C14 C13 1_555 1_555 1_555 1_555 -178.3(4) no C9 C10 C11 C12 1_555 1_555 1_555 1_555 0.8(7) no C9 C14 C13 C12 1_555 1_555 1_555 1_555 0.0(7) no C9 C14 C13 C15 1_555 1_555 1_555 1_555 -177.5(4) no C10 C9 C14 C13 1_555 1_555 1_555 1_555 1.7(7) no C10 C11 C12 C13 1_555 1_555 1_555 1_555 1.1(6) no C11 C10 C9 C14 1_555 1_555 1_555 1_555 -2.1(6) no C11 C12 C13 C14 1_555 1_555 1_555 1_555 -1.4(6) no C11 C12 C13 C15 1_555 1_555 1_555 1_555 176.0(4) no C12 C13 C15 C16 1_555 1_555 1_555 1_555 -148(8) no C13 C15 C16 C17 1_555 1_555 1_555 1_555 2E1(5) no C14 C13 C15 C16 1_555 1_555 1_555 1_555 29(8) no C15 C16 C17 C18 1_555 1_555 1_555 1_555 -1E1(4) no C15 C16 C17 C22 1_555 1_555 1_555 1_555 17E1(4) no C16 C17 C18 C19 1_555 1_555 1_555 1_555 177.7(4) no C16 C17 C22 C21 1_555 1_555 1_555 1_555 -178.8(5) no C17 C18 C19 C20 1_555 1_555 1_555 1_555 1.8(8) no C17 C22 C21 C20 1_555 1_555 1_555 1_555 0.5(8) no C18 C17 C22 C21 1_555 1_555 1_555 1_555 0.9(7) no C18 C19 C20 C21 1_555 1_555 1_555 1_555 -0.3(8) no C19 C18 C17 C22 1_555 1_555 1_555 1_555 -2.1(7) no C19 C20 C21 C22 1_555 1_555 1_555 1_555 -0.8(8) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21128903 2 PubChem 12996294