#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/66/2206637.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_2206637 loop_ _publ_author_name 'Jones, Peter G.' 'Ku\'s, Piotr' _publ_section_title ; 2,2''-Bis(bromomethyl)-p-terphenyl ; _journal_coeditor_code BT6714 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2947 _journal_page_last o2948 _journal_paper_doi 10.1107/S1600536805025614 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C20 H16 Br2' _chemical_formula_moiety 'C20 H16 Br2' _chemical_formula_sum 'C20 H16 Br2' _chemical_formula_weight 416.15 _chemical_name_systematic ; 2,2''-bis(bromomethyl)-p-terphenyl ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens riding _atom_sites_solution_primary Patterson _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 96.032(4) _cell_angle_beta 98.347(4) _cell_angle_gamma 96.155(4) _cell_formula_units_Z 1 _cell_length_a 4.4286(4) _cell_length_b 7.4756(6) _cell_length_c 12.4664(12) _cell_measurement_reflns_used 4465 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 30.4 _cell_measurement_theta_min 2.7 _cell_volume 402.93(6) _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics 'XP (Siemens, 1994)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 133(2) _diffrn_detector_area_resol_mean 8.192 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method '\w and \f' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 8315 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.03 _diffrn_reflns_theta_min 1.66 _exptl_absorpt_coefficient_mu 5.023 _exptl_absorpt_correction_T_max 0.704 _exptl_absorpt_correction_T_min 0.488 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1998)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.715 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular prism' _exptl_crystal_F_000 206 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.631 _refine_diff_density_min -0.329 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 100 _refine_ls_number_reflns 2348 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.022 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0246 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.032P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.0573 _reflns_number_gt 2056 _reflns_number_total 2348 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6714.cif _cod_data_source_block I _cod_database_code 2206637 _cod_database_fobs_code 2206637 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_refinement_flags _atom_site_occupancy _atom_site_type_symbol Br 0.25108(4) 0.34454(2) 0.100201(14) 0.02420(7) Uani d . 1 Br C1 0.5066(4) 0.3147(2) 0.48155(14) 0.0205(3) Uani d . 1 C H1 0.5108 0.1876 0.4682 0.025 Uiso calc R 1 H C2 0.5393(4) 0.4203(2) 0.39786(13) 0.0210(4) Uani d . 1 C H2 0.5667 0.3648 0.3284 0.025 Uiso calc R 1 H C3 0.5324(4) 0.6086(2) 0.41475(13) 0.0185(3) Uani d . 1 C C4 0.5764(4) 0.7268(2) 0.32756(13) 0.0179(3) Uani d . 1 C C5 0.3932(4) 0.6977(2) 0.22374(13) 0.0173(3) Uani d . 1 C C6 0.4493(4) 0.8159(2) 0.14722(14) 0.0208(3) Uani d . 1 C H6 0.3256 0.7964 0.0771 0.025 Uiso calc R 1 H C7 0.6806(4) 0.9607(2) 0.17112(15) 0.0240(4) Uani d . 1 C H7 0.7165 1.0387 0.1176 0.029 Uiso calc R 1 H C8 0.8594(5) 0.9909(2) 0.27374(16) 0.0252(4) Uani d . 1 C H8 1.0179 1.0903 0.2912 0.030 Uiso calc R 1 H C9 0.8057(4) 0.8749(2) 0.35103(14) 0.0225(4) Uani d . 1 C H9 0.9278 0.8971 0.4214 0.027 Uiso calc R 1 H C10 0.1314(4) 0.5490(2) 0.19254(14) 0.0196(3) Uani d . 1 C H10A -0.0464 0.5961 0.1521 0.024 Uiso calc R 1 H H10B 0.0685 0.5057 0.2593 0.024 Uiso calc R 1 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 Br 0.02757(12) 0.02080(10) 0.02267(10) 0.00043(7) 0.00274(7) -0.00022(6) C1 0.0259(10) 0.0172(8) 0.0187(8) 0.0053(7) 0.0032(6) 0.0016(6) C2 0.0265(10) 0.0219(8) 0.0150(8) 0.0065(7) 0.0036(6) 0.0006(6) C3 0.0190(9) 0.0206(8) 0.0163(7) 0.0040(6) 0.0020(6) 0.0037(6) C4 0.0201(9) 0.0175(8) 0.0176(7) 0.0057(6) 0.0044(6) 0.0030(6) C5 0.0178(9) 0.0176(8) 0.0176(8) 0.0054(6) 0.0046(6) 0.0022(6) C6 0.0230(10) 0.0221(8) 0.0183(8) 0.0054(7) 0.0026(6) 0.0052(6) C7 0.0280(11) 0.0197(8) 0.0276(9) 0.0051(7) 0.0092(7) 0.0086(7) C8 0.0258(11) 0.0187(8) 0.0298(9) -0.0013(7) 0.0040(7) 0.0013(7) C9 0.0246(10) 0.0214(9) 0.0200(8) 0.0027(7) 0.0010(7) -0.0004(7) C10 0.0191(9) 0.0213(8) 0.0186(8) 0.0028(6) 0.0030(6) 0.0025(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle C2 C1 C3 . 2_666 121.42(16) C1 C2 C3 . . 120.71(15) C1 C3 C2 2_666 . 117.87(15) C1 C3 C4 2_666 . 120.05(15) C2 C3 C4 . . 122.04(15) C9 C4 C5 . . 118.65(15) C9 C4 C3 . . 118.39(15) C5 C4 C3 . . 122.95(16) C6 C5 C4 . . 119.13(16) C6 C5 C10 . . 118.04(15) C4 C5 C10 . . 122.79(15) C7 C6 C5 . . 121.58(16) C6 C7 C8 . . 119.43(16) C7 C8 C9 . . 119.70(17) C8 C9 C4 . . 121.50(17) C5 C10 Br . . 110.67(12) C2 C1 H1 . . 119.3 C3 C1 H1 2_666 . 119.3 C1 C2 H2 . . 119.6 C3 C2 H2 . . 119.6 C7 C6 H6 . . 119.2 C5 C6 H6 . . 119.2 C6 C7 H7 . . 120.3 C8 C7 H7 . . 120.3 C7 C8 H8 . . 120.2 C9 C8 H8 . . 120.2 C8 C9 H9 . . 119.2 C4 C9 H9 . . 119.2 C5 C10 H10A . . 109.5 Br C10 H10A . . 109.5 C5 C10 H10B . . 109.5 Br C10 H10B . . 109.5 H10A C10 H10B . . 108.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance Br C10 . 1.9806(17) C1 C2 . 1.388(2) C1 C3 2_666 1.400(2) C2 C3 . 1.405(2) C3 C4 . 1.492(2) C4 C9 . 1.395(2) C4 C5 . 1.407(2) C5 C6 . 1.397(2) C5 C10 . 1.494(2) C6 C7 . 1.384(3) C7 C8 . 1.386(3) C8 C9 . 1.391(3) C1 H1 . 0.9500 C2 H2 . 0.9500 C6 H6 . 0.9500 C7 H7 . 0.9500 C8 H8 . 0.9500 C9 H9 . 0.9500 C10 H10A . 0.9900 C10 H10B . 0.9900 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C6 H6 Br 2_565 0.95 3.13 4.0272(18) 158 C7 H7 Br 1_665 0.95 3.16 3.8764(18) 134 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_4 _geom_torsion C3 C1 C2 C3 2_666 . -0.4(3) C1 C2 C3 C1 . 2_666 0.4(3) C1 C2 C3 C4 . . 178.10(17) C1 C3 C4 C9 2_666 . 52.3(2) C2 C3 C4 C9 . . -125.40(19) C1 C3 C4 C5 2_666 . -126.36(19) C2 C3 C4 C5 . . 55.9(3) C9 C4 C5 C6 . . 0.9(2) C3 C4 C5 C6 . . 179.58(16) C9 C4 C5 C10 . . -176.70(16) C3 C4 C5 C10 . . 2.0(3) C4 C5 C6 C7 . . 0.0(3) C10 C5 C6 C7 . . 177.77(16) C5 C6 C7 C8 . . -0.7(3) C6 C7 C8 C9 . . 0.4(3) C7 C8 C9 C4 . . 0.6(3) C5 C4 C9 C8 . . -1.2(3) C3 C4 C9 C8 . . -179.95(16) C6 C5 C10 Br . . 79.98(17) C4 C5 C10 Br . . -102.37(16) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 12697716