#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/21/2102180.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_2102180 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 Cl2 O' _chemical_formula_sum 'C15 H10 Cl2 O' _chemical_formula_weight 277.13 _chemical_melting_point 72.5(5) _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 117.240(1) _cell_angle_beta 99.250(1) _cell_angle_gamma 96.860(1) _cell_formula_units_Z 2 _cell_length_a 5.7280(1) _cell_length_b 11.3620(2) _cell_length_c 11.5210(1) _cell_measurement_reflns_used 25 _cell_measurement_temperature 150 _cell_volume 641.866(19) _computing_cell_refinement 'SXD (Keen & Wilson, 1996)' _computing_data_collection 'SXD (Keen & Wilson, 1996)' _computing_data_reduction 'SXD (Keen & Wilson, 1996)' _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_measured_fraction_theta_full 0.197 _diffrn_measured_fraction_theta_max 0.197 _diffrn_measurement_device_type SXD _diffrn_measurement_method 'time-of-flight LAUE diffraction' _diffrn_radiation_monochromator none _diffrn_radiation_probe neutron _diffrn_radiation_source 'ISIS spallation source' _diffrn_radiation_type neutron _diffrn_radiation_wavelength 0.5-5.0 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_av_sigmaI/netI 0.031 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 10674 _diffrn_reflns_theta_full 16.16 _diffrn_reflns_theta_max 16.16 _diffrn_reflns_theta_min 1.25 _exptl_absorpt_coefficient_mu '1.450 at 1 angstrom' _exptl_absorpt_correction_T_max 0.89 _exptl_absorpt_correction_T_min 0.51 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ; The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 0.64 + 0.81 * lambda [cm^-1] ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 284 _exptl_crystal_size_max 2.5 _exptl_crystal_size_mid 1.5 _exptl_crystal_size_min 1.0 _refine_ls_extinction_coef 0.296 _refine_ls_extinction_method 'Becker-Coppens Lorentzian model' _refine_ls_goodness_of_fit_ref 5.444 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 253 _refine_ls_number_reflns 2929 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 5.444 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0668 _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^)]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1281 _refine_ls_wR_factor_ref 0.1281 _reflns_number_gt 2928 _reflns_number_total 2929 _reflns_threshold_expression >2sigma(I) _cod_data_source_file bm0034.cif _cod_data_source_block 3N _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '72-73' was changed to '72.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '72-73' was changed to '72.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 641.865(17) _cod_original_sg_symbol_H-M P-1 _cod_database_code 2102180 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 C1 C 1.0047(4) -0.02661(18) 0.3033(2) 0.0333(5) Uani 1 1 d C2 C 0.9559(3) 0.08311(16) 0.35113(19) 0.0223(4) Uani 1 1 d C3 C 0.8984(3) 0.21786(15) 0.40894(17) 0.0187(3) Uani 1 1 d O1 O 1.1102(4) 0.3181(2) 0.4452(3) 0.0268(5) Uani 1 1 d C4 C 0.8194(3) 0.24703(14) 0.53838(16) 0.0171(3) Uani 1 1 d C5 C 0.9649(3) 0.34106(16) 0.66423(18) 0.0236(4) Uani 1 1 d C6 C 0.8860(4) 0.36646(17) 0.78000(19) 0.0269(4) Uani 1 1 d C7 C 0.6603(3) 0.29618(17) 0.76792(18) 0.0236(4) Uani 1 1 d Cl1 Cl 0.0542(3) 0.26511(16) 0.05897(17) 0.0421(4) Uani 1 1 d C8 C 0.5148(4) 0.2012(2) 0.6435(2) 0.0278(4) Uani 1 1 d C9 C 0.5950(3) 0.17659(18) 0.52866(19) 0.0247(4) Uani 1 1 d C10 C 0.6940(3) 0.22635(15) 0.31199(17) 0.0193(3) Uani 1 1 d C11 C 0.6513(4) 0.35329(16) 0.34004(19) 0.0248(4) Uani 1 1 d C12 C 0.4579(4) 0.36662(18) 0.2611(2) 0.0282(4) Uani 1 1 d C13 C 0.3053(4) 0.25032(18) 0.15295(19) 0.0266(4) Uani 1 1 d Cl2 Cl 0.5579(3) 0.32699(17) 0.91032(17) 0.0434(4) Uani 1 1 d C14 C 0.3467(4) 0.12323(18) 0.1226(2) 0.0299(4) Uani 1 1 d C15 C 0.5422(4) 0.11157(17) 0.20187(19) 0.0265(4) Uani 1 1 d H11 H 0.7679(9) 0.4433(4) 0.4257(5) 0.0482(12) Uani 1 1 d H15 H 0.5713(10) 0.0116(4) 0.1802(5) 0.0514(13) Uani 1 1 d H5 H 1.1370(10) 0.3966(5) 0.6715(5) 0.0532(12) Uani 1 1 d H9 H 0.4800(9) 0.1024(5) 0.4320(5) 0.0549(12) Uani 1 1 d H6 H 0.9997(11) 0.4397(5) 0.8769(5) 0.0602(14) Uani 1 1 d H8 H 0.3403(10) 0.1454(6) 0.6355(6) 0.0570(13) Uani 1 1 d H14 H 0.2271(10) 0.0345(5) 0.0377(5) 0.0556(13) Uani 1 1 d H12 H 0.4225(10) 0.4649(4) 0.2825(5) 0.0560(14) Uani 1 1 d HA H 1.1791(10) 0.2951(5) 0.3698(6) 0.0572(13) Uani 1 1 d H1 H 1.0485(11) -0.1217(5) 0.2613(7) 0.0671(17) Uani 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 C1 0.0287(11) 0.0237(8) 0.0470(13) 0.0148(8) 0.0121(9) 0.0100(8) C2 0.0192(9) 0.0190(7) 0.0289(9) 0.0108(7) 0.0085(7) 0.0048(6) C3 0.0153(8) 0.0174(6) 0.0221(8) 0.0090(6) 0.0049(6) 0.0006(6) O1 0.0202(11) 0.0236(9) 0.0343(13) 0.0136(9) 0.0080(10) -0.0032(8) C4 0.0151(8) 0.0152(6) 0.0199(8) 0.0083(6) 0.0034(6) 0.0012(6) C5 0.0220(10) 0.0198(7) 0.0235(9) 0.0081(7) 0.0035(7) -0.0017(6) C6 0.0285(10) 0.0229(8) 0.0229(9) 0.0076(7) 0.0036(8) 0.0023(7) C7 0.0234(10) 0.0264(8) 0.0242(9) 0.0129(7) 0.0077(7) 0.0113(7) Cl1 0.0406(10) 0.0509(9) 0.0404(9) 0.0282(7) 0.0027(7) 0.0138(7) C8 0.0196(10) 0.0382(9) 0.0264(10) 0.0164(8) 0.0073(8) 0.0037(8) C9 0.0151(9) 0.0315(9) 0.0232(9) 0.0123(7) 0.0031(7) -0.0041(7) C10 0.0215(9) 0.0156(6) 0.0209(8) 0.0090(6) 0.0062(7) 0.0024(6) C11 0.0281(10) 0.0165(7) 0.0283(9) 0.0118(7) 0.0030(8) 0.0010(7) C12 0.0324(11) 0.0241(8) 0.0333(10) 0.0183(8) 0.0071(8) 0.0069(7) C13 0.0287(10) 0.0302(8) 0.0245(9) 0.0164(7) 0.0057(8) 0.0065(7) Cl2 0.0442(10) 0.0591(10) 0.0338(8) 0.0230(7) 0.0194(7) 0.0204(8) C14 0.0303(11) 0.0274(9) 0.0260(10) 0.0101(8) 0.0012(8) 0.0048(8) C15 0.0301(11) 0.0187(7) 0.0241(9) 0.0067(6) 0.0022(8) 0.0044(7) H11 0.051(3) 0.0268(17) 0.053(3) 0.0147(18) -0.002(2) -0.0004(17) H15 0.057(3) 0.0279(18) 0.053(3) 0.0118(17) -0.002(2) 0.0089(18) H5 0.042(3) 0.052(2) 0.045(3) 0.016(2) 0.003(2) -0.018(2) H9 0.035(3) 0.071(3) 0.036(2) 0.019(2) -0.001(2) -0.022(2) H6 0.063(4) 0.054(3) 0.034(2) 0.005(2) 0.001(2) -0.008(2) H8 0.035(3) 0.079(3) 0.059(3) 0.038(3) 0.015(2) -0.003(2) H14 0.053(3) 0.044(2) 0.044(3) 0.008(2) -0.007(2) 0.002(2) H12 0.063(3) 0.037(2) 0.070(3) 0.031(2) 0.005(3) 0.015(2) HA 0.052(3) 0.057(3) 0.059(3) 0.023(2) 0.032(3) -0.005(2) H1 0.070(4) 0.039(2) 0.093(4) 0.026(3) 0.029(3) 0.029(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_length_neutron _atom_type_scat_source C C 6.646 'International Tables Vol C Tables 4.4.4.1' H H -3.739 'International Tables Vol C Tables 4.4.4.1' O O 5.803 'International Tables Vol C Tables 4.4.4.1' Cl Cl 9.577 'International Tables Vol C Tables 4.4.4.1' 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_3 C2 C1 H1 179.4(5) . C1 C2 C3 179.3(2) . O1 C3 C2 109.59(16) . O1 C3 C10 110.84(15) . C2 C3 C10 111.64(14) . O1 C3 C4 107.04(16) . C2 C3 C4 108.89(13) . C10 C3 C4 108.70(14) . C3 O1 HA 109.4(4) . C5 C4 C9 119.38(17) . C5 C4 C3 121.94(16) . C9 C4 C3 118.69(15) . C4 C5 C6 120.45(18) . C4 C5 H5 119.3(3) . C6 C5 H5 120.2(3) . C7 C6 C5 119.22(17) . C7 C6 H6 120.9(4) . C5 C6 H6 119.9(4) . C8 C7 C6 120.99(19) . C8 C7 Cl2 119.03(17) . C6 C7 Cl2 119.98(15) . C7 C8 C9 119.38(19) . C7 C8 H8 120.3(4) . C9 C8 H8 120.3(4) . C8 C9 C4 120.58(17) . C8 C9 H9 118.8(3) . C4 C9 H9 120.6(3) . C15 C10 C11 119.24(15) . C15 C10 C3 122.25(13) . C11 C10 C3 118.41(14) . C12 C11 C10 120.99(16) . C12 C11 H11 119.1(3) . C10 C11 H11 119.9(3) . C11 C12 C13 118.87(15) . C11 C12 H12 121.6(3) . C13 C12 H12 119.6(3) . C14 C13 C12 120.92(16) . C14 C13 Cl1 119.74(15) . C12 C13 Cl1 119.29(13) . C7 Cl2 Cl1 93.85(9) 1_656 C13 C14 C15 119.54(17) . C13 C14 H14 119.7(3) . C15 C14 H14 120.8(3) . C14 C15 C10 120.42(14) . C14 C15 H15 119.6(3) . C10 C15 H15 119.9(3) . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 C2 1.200(2) . C1 H1 1.044(4) . C2 C3 1.467(2) . C3 O1 1.420(3) . C3 C10 1.528(2) . C3 C4 1.529(3) . O1 HA 0.951(7) . C4 C5 1.385(2) . C4 C9 1.390(3) . C5 C6 1.393(3) . C5 H5 1.074(6) . C6 C7 1.386(3) . C6 H6 1.072(5) . C7 C8 1.378(3) . C7 Cl2 1.729(3) . Cl1 C13 1.730(2) . C8 C9 1.389(3) . C8 H8 1.084(6) . C9 H9 1.075(5) . C10 C15 1.388(2) . C10 C11 1.388(2) . C11 C12 1.385(3) . C11 H11 1.080(5) . C12 C13 1.389(3) . C12 H12 1.080(4) . C13 C14 1.382(2) . Cl2 Cl1 3.394(2) 1_656 C14 C15 1.387(3) . C14 H14 1.077(5) . C15 H15 1.086(4) . loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 225156