#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/21/2102181.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_2102181 loop_ _publ_author_name 'Bilton, Clair' 'Howard, Judith A. K.' 'Madhavi, N. N. L.' 'Nangia, Ashwini' 'Desiraju, Gautam R.' 'Allen, Frank H.' 'Wilson, Chick C.' _publ_section_title ; Crystal engineering in the gem-alkynol family; synthon repetitivity and topological similarity in diphenylethynylmethanols: structures that lack O---H···O hydrogen bonds ; _journal_coeditor_code BM0034 _journal_issue 6 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 1071 _journal_page_last 1079 _journal_paper_doi 10.1107/S010876810001154X _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C15 H10 Br2 O' _chemical_formula_sum 'C15 H10 Br2 O' _chemical_formula_weight 366.05 _chemical_melting_point 97 _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 difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 115.67(3) _cell_angle_beta 99.43(3) _cell_angle_gamma 97.91(3) _cell_formula_units_Z 2 _cell_length_a 5.7906(12) _cell_length_b 11.325(2) _cell_length_c 11.907(2) _cell_measurement_reflns_used 998 _cell_measurement_temperature 150 _cell_measurement_theta_max 30.50 _cell_measurement_theta_min 4.26 _cell_volume 674.9(3) _computing_cell_refinement 'Bruker SMART (Bruker Systems Inc., 1999a)' _computing_data_collection 'Bruker SMART (Bruker Systems Inc., 1999a)' _computing_data_reduction 'Bruker SAINT (Bruker Systems Inc., 1999b)' _computing_molecular_graphics 'SHELXL97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150 _diffrn_detector_area_resol_mean 'not relevant' _diffrn_measured_fraction_theta_full 0.867 _diffrn_measured_fraction_theta_max 0.867 _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method \w _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 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 5364 _diffrn_reflns_theta_full 30.16 _diffrn_reflns_theta_max 30.16 _diffrn_reflns_theta_min 1.96 _exptl_absorpt_coefficient_mu 5.990 _exptl_absorpt_correction_T_max 0.766 _exptl_absorpt_correction_T_min 0.344 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(XPREP in SHELX97; Sheldrick, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.801 _exptl_crystal_density_meas ? _exptl_crystal_density_method . _exptl_crystal_description block _exptl_crystal_F_000 356 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.862 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.084 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 203 _refine_ls_number_reflns 3456 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0276 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+0.1818P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0691 _refine_ls_wR_factor_ref 0.0718 _reflns_number_gt 2879 _reflns_number_total 3456 _reflns_threshold_expression >2sigma(I) _cod_data_source_file bm0034.cif _cod_data_source_block 4 _cod_original_cell_volume 674.8(2) _cod_original_sg_symbol_H-M P-1 _cod_database_code 2102181 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag Br1 Br 1.45503(4) 0.23580(3) 1.44526(2) 0.03392(8) Uani 1 1 d Br2 Br 0.95564(5) 0.17469(3) 0.60197(2) 0.03739(8) Uani 1 1 d O1 O 0.3788(3) 0.17949(17) 1.05754(17) 0.0280(3) Uani 1 1 d C10 C 0.6726(4) 0.2554(2) 0.9690(2) 0.0208(4) Uani 1 1 d C15 C 0.8996(4) 0.3258(2) 0.9790(2) 0.0250(4) Uani 1 1 d C14 C 0.9833(4) 0.3029(2) 0.8698(2) 0.0263(4) Uani 1 1 d C3 C 0.5921(4) 0.2826(2) 1.0935(2) 0.0222(4) Uani 1 1 d C2 C 0.5352(4) 0.4170(2) 1.1473(2) 0.0243(4) Uani 1 1 d C12 C 0.6082(4) 0.1394(2) 0.7376(2) 0.0260(4) Uani 1 1 d C11 C 0.5266(4) 0.1636(2) 0.8476(2) 0.0242(4) Uani 1 1 d C5 C 0.9410(4) 0.3879(2) 1.2966(2) 0.0283(5) Uani 1 1 d C1 C 0.4884(4) 0.5239(3) 1.1907(3) 0.0314(5) Uani 1 1 d C4 C 0.7950(4) 0.2749(2) 1.1894(2) 0.0220(4) Uani 1 1 d C13 C 0.8365(4) 0.2090(2) 0.7505(2) 0.0247(4) Uani 1 1 d C7 C 1.1801(4) 0.2507(2) 1.3444(2) 0.0261(4) Uani 1 1 d C8 C 1.0325(4) 0.1356(2) 1.2387(2) 0.0274(4) Uani 1 1 d C6 C 1.1362(4) 0.3768(2) 1.3750(2) 0.0297(5) Uani 1 1 d C9 C 0.8406(4) 0.1481(2) 1.1613(2) 0.0263(4) Uani 1 1 d H5 H 0.909(5) 0.474(3) 1.312(3) 0.028(7) Uiso 1 1 d H8 H 1.066(5) 0.052(3) 1.219(3) 0.038(8) Uiso 1 1 d H15 H 0.994(5) 0.384(3) 1.057(3) 0.028(7) Uiso 1 1 d H6 H 1.216(6) 0.454(3) 1.441(3) 0.054(10) Uiso 1 1 d H14 H 1.135(6) 0.350(3) 0.878(3) 0.039(8) Uiso 1 1 d H11 H 0.387(6) 0.115(3) 0.834(3) 0.036(8) Uiso 1 1 d H9 H 0.758(5) 0.075(3) 1.094(3) 0.037(8) Uiso 1 1 d H12 H 0.513(5) 0.076(3) 0.654(3) 0.034(7) Uiso 1 1 d H1A H 0.327(6) 0.199(3) 1.117(3) 0.047(10) Uiso 1 1 d H1 H 0.434(7) 0.600(4) 1.213(4) 0.064(11) Uiso 1 1 d 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 0.03509(14) 0.03848(14) 0.02954(13) 0.01819(11) 0.00334(9) 0.01039(10) Br2 0.03590(14) 0.05276(17) 0.02461(12) 0.01505(11) 0.01266(9) 0.01797(11) O1 0.0243(8) 0.0249(8) 0.0304(9) 0.0105(7) 0.0089(7) -0.0017(6) C10 0.0208(9) 0.0189(9) 0.0228(10) 0.0102(8) 0.0050(8) 0.0041(7) C15 0.0214(10) 0.0274(11) 0.0221(10) 0.0102(9) 0.0027(8) 0.0008(8) C14 0.0200(10) 0.0329(11) 0.0252(11) 0.0130(9) 0.0061(8) 0.0049(8) C3 0.0206(9) 0.0191(9) 0.0243(10) 0.0089(8) 0.0064(8) 0.0009(7) C2 0.0199(9) 0.0262(10) 0.0247(10) 0.0106(9) 0.0056(8) 0.0035(8) C12 0.0281(11) 0.0220(10) 0.0204(10) 0.0057(9) -0.0006(8) 0.0052(8) C11 0.0212(10) 0.0191(10) 0.0283(11) 0.0097(9) 0.0033(8) 0.0006(8) C5 0.0337(12) 0.0226(11) 0.0245(11) 0.0080(9) 0.0046(9) 0.0070(9) C1 0.0262(11) 0.0278(12) 0.0372(13) 0.0122(10) 0.0076(9) 0.0077(9) C4 0.0255(10) 0.0205(10) 0.0220(10) 0.0109(8) 0.0089(8) 0.0044(8) C13 0.0281(11) 0.0277(11) 0.0235(10) 0.0134(9) 0.0094(8) 0.0138(9) C7 0.0272(10) 0.0315(12) 0.0230(10) 0.0153(9) 0.0070(8) 0.0075(9) C8 0.0301(11) 0.0231(11) 0.0311(11) 0.0147(9) 0.0075(9) 0.0057(8) C6 0.0340(12) 0.0248(11) 0.0216(11) 0.0058(9) 0.0015(9) 0.0040(9) C9 0.0290(11) 0.0208(10) 0.0254(11) 0.0094(9) 0.0050(8) 0.0016(8) 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' O O 0.0106 0.0060 '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 C3 O1 H1A 107(3) C11 C10 C15 119.2(2) C11 C10 C3 122.18(19) C15 C10 C3 118.60(19) C14 C15 C10 121.0(2) C14 C15 H15 119.6(18) C10 C15 H15 119.4(18) C13 C14 C15 118.6(2) C13 C14 H14 121(2) C15 C14 H14 120(2) O1 C3 C2 109.93(18) O1 C3 C4 110.93(17) C2 C3 C4 111.32(18) O1 C3 C10 106.56(17) C2 C3 C10 109.10(17) C4 C3 C10 108.86(17) C1 C2 C3 179.4(2) C13 C12 C11 119.1(2) C13 C12 H12 118.7(17) C11 C12 H12 122.1(17) C12 C11 C10 120.4(2) C12 C11 H11 115(2) C10 C11 H11 125(2) C4 C5 C6 120.7(2) C4 C5 H5 117.6(17) C6 C5 H5 121.6(17) C2 C1 H1 172(3) C5 C4 C9 119.3(2) C5 C4 C3 122.84(19) C9 C4 C3 117.7(2) C14 C13 C12 121.6(2) C14 C13 Br2 118.38(17) C12 C13 Br2 120.01(17) C6 C7 C8 121.2(2) C6 C7 Br1 119.26(18) C8 C7 Br1 119.49(17) C9 C8 C7 119.2(2) C9 C8 H8 120.7(19) C7 C8 H8 120.1(19) C7 C6 C5 119.0(2) C7 C6 H6 127(2) C5 C6 H6 114(2) C8 C9 C4 120.5(2) C8 C9 H9 117(2) C4 C9 H9 123(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C7 1.904(2) Br2 C13 1.906(2) O1 C3 1.438(3) O1 H1A 0.76(3) C10 C11 1.393(3) C10 C15 1.398(3) C10 C3 1.543(3) C15 C14 1.394(3) C15 H15 0.90(3) C14 C13 1.385(3) C14 H14 0.93(3) C3 C2 1.483(3) C3 C4 1.538(3) C2 C1 1.184(3) C12 C13 1.391(3) C12 C11 1.393(3) C12 H12 0.95(3) C11 H11 0.86(3) C5 C4 1.384(3) C5 C6 1.400(3) C5 H5 0.97(3) C1 H1 0.90(4) C4 C9 1.401(3) C7 C6 1.385(3) C7 C8 1.390(3) C8 C9 1.387(3) C8 H8 0.93(3) C6 H6 0.88(4) C9 H9 0.86(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21140566 2 PubChem 102243277