#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/21/2102178.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_2102178 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_volume 56 _journal_year 2000 _chemical_formula_moiety 'C17 H16 O' _chemical_formula_sum 'C17 H16 O' _chemical_formula_weight 236.30 _chemical_melting_point 95.5(5) _chemical_name_systematic ; ? ; _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 106.73(3) _cell_angle_beta 98.71(3) _cell_angle_gamma 101.39(3) _cell_formula_units_Z 2 _cell_length_a 6.8286(14) _cell_length_b 8.2407(16) _cell_length_c 12.658(3) _cell_measurement_reflns_used 512 _cell_measurement_temperature 150 _cell_measurement_theta_max 29.35 _cell_measurement_theta_min 5.33 _cell_volume 652.0(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_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _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 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4775 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 1.72 _diffrn_standards_number 'not relevant' _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.784 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 252 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.205 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 231 _refine_ls_number_reflns 2964 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0478 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.004 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0618P)^2^+0.2678P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1199 _refine_ls_wR_factor_ref 0.1317 _reflns_number_gt 2362 _reflns_number_total 2964 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file bm0034.cif _[local]_cod_data_source_block 2 _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '95-96' was changed to '95.5(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 '95-96' was changed to '95.5(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 652.0(2) _cod_database_code 2102178 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 _atom_site_refinement_flags H1 H 0.759(3) -0.095(3) 0.3239(19) 0.052(6) Uiso 1 1 d . C1 C 0.7141(3) -0.0109(2) 0.29487(14) 0.0344(4) Uani 1 1 d . C2 C 0.6603(2) 0.09261(19) 0.25638(13) 0.0266(3) Uani 1 1 d . C3 C 0.5790(2) 0.21385(18) 0.20481(12) 0.0229(3) Uani 1 1 d . O1 O 0.36138(16) 0.14659(15) 0.16398(10) 0.0278(3) Uani 1 1 d . HA H 0.348(4) 0.043(3) 0.119(2) 0.060(7) Uiso 1 1 d . C4 C 0.6155(2) 0.39365(18) 0.29666(12) 0.0224(3) Uani 1 1 d . C5 C 0.4550(2) 0.4686(2) 0.31962(14) 0.0277(3) Uani 1 1 d . H5 H 0.314(3) 0.409(3) 0.2785(18) 0.044(6) Uiso 1 1 d . C6 C 0.4927(3) 0.6303(2) 0.40489(14) 0.0303(4) Uani 1 1 d . H6 H 0.378(3) 0.683(3) 0.4221(16) 0.039(5) Uiso 1 1 d . C7 C 0.6903(2) 0.71997(19) 0.46824(12) 0.0263(3) Uani 1 1 d . C8 C 0.7306(3) 0.8924(2) 0.56227(15) 0.0356(4) Uani 1 1 d . H8A H 0.837(4) 0.987(4) 0.554(2) 0.077(8) Uiso 1 1 d . H8B H 0.606(5) 0.934(4) 0.570(2) 0.088(9) Uiso 1 1 d . H8C H 0.783(4) 0.882(4) 0.636(2) 0.077(8) Uiso 1 1 d . C9 C 0.8508(2) 0.6444(2) 0.44306(13) 0.0281(3) Uani 1 1 d . H9 H 0.990(3) 0.702(2) 0.4848(16) 0.032(5) Uiso 1 1 d . C10 C 0.8142(2) 0.4830(2) 0.35843(13) 0.0272(3) Uani 1 1 d . H10 H 0.932(3) 0.432(3) 0.3424(17) 0.043(5) Uiso 1 1 d . C11 C 0.6815(2) 0.23500(17) 0.10758(12) 0.0222(3) Uani 1 1 d . C12 C 0.5842(2) 0.29838(19) 0.02815(13) 0.0260(3) Uani 1 1 d . H12 H 0.453(3) 0.324(2) 0.0344(16) 0.034(5) Uiso 1 1 d . C13 C 0.6724(3) 0.3212(2) -0.06040(13) 0.0282(3) Uani 1 1 d . H13 H 0.601(3) 0.361(3) -0.1146(18) 0.044(6) Uiso 1 1 d . C14 C 0.8597(2) 0.28299(18) -0.07268(13) 0.0266(3) Uani 1 1 d . C15 C 0.9529(3) 0.3045(2) -0.17029(15) 0.0362(4) Uani 1 1 d . H15A H 1.010(7) 0.206(6) -0.202(4) 0.045(11) Uiso 0.50 1 d P H66 H 1.112(7) 0.323(6) -0.152(4) 0.043(11) Uiso 0.50 1 d P H15B H 0.994(5) 0.421(4) -0.168(3) 0.095(10) Uiso 1 1 d . H15C H 0.854(5) 0.250(4) -0.241(3) 0.090(9) Uiso 1 1 d . C16 C 0.9569(2) 0.22143(19) 0.00761(13) 0.0266(3) Uani 1 1 d . H16 H 1.086(3) 0.192(2) 0.0026(16) 0.031(5) Uiso 1 1 d . C17 C 0.8691(2) 0.19732(19) 0.09667(13) 0.0248(3) Uani 1 1 d . H17 H 0.939(3) 0.152(2) 0.1506(15) 0.027(4) 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 C1 0.0441(10) 0.0283(8) 0.0350(9) 0.0148(7) 0.0101(7) 0.0110(7) C2 0.0292(8) 0.0220(7) 0.0261(7) 0.0061(6) 0.0066(6) 0.0033(6) C3 0.0223(7) 0.0198(7) 0.0249(7) 0.0065(6) 0.0031(5) 0.0039(5) O1 0.0227(5) 0.0230(5) 0.0319(6) 0.0050(5) 0.0030(4) 0.0013(4) C4 0.0269(7) 0.0197(6) 0.0215(7) 0.0084(5) 0.0056(5) 0.0053(5) C5 0.0243(8) 0.0247(7) 0.0314(8) 0.0072(6) 0.0039(6) 0.0051(6) C6 0.0307(8) 0.0263(8) 0.0356(9) 0.0088(7) 0.0101(7) 0.0111(6) C7 0.0351(8) 0.0216(7) 0.0229(7) 0.0088(6) 0.0082(6) 0.0057(6) C8 0.0460(10) 0.0252(8) 0.0309(9) 0.0026(7) 0.0106(7) 0.0070(7) C9 0.0279(8) 0.0263(7) 0.0253(7) 0.0064(6) 0.0023(6) 0.0019(6) C10 0.0253(8) 0.0253(7) 0.0294(8) 0.0063(6) 0.0060(6) 0.0066(6) C11 0.0239(7) 0.0161(6) 0.0227(7) 0.0035(5) 0.0027(5) 0.0028(5) C12 0.0253(8) 0.0237(7) 0.0284(8) 0.0081(6) 0.0033(6) 0.0073(6) C13 0.0341(8) 0.0240(7) 0.0252(7) 0.0087(6) 0.0018(6) 0.0070(6) C14 0.0328(8) 0.0172(6) 0.0243(7) 0.0020(5) 0.0068(6) 0.0007(6) C15 0.0494(11) 0.0275(8) 0.0296(9) 0.0055(7) 0.0157(8) 0.0053(8) C16 0.0243(7) 0.0218(7) 0.0313(8) 0.0051(6) 0.0066(6) 0.0056(6) C17 0.0254(7) 0.0205(7) 0.0262(7) 0.0063(6) 0.0024(6) 0.0053(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' O O 0.0106 0.0060 '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 C2 C1 H1 178.4(14) C1 C2 C3 176.11(17) O1 C3 C2 108.99(12) O1 C3 C11 110.27(12) C2 C3 C11 111.00(12) O1 C3 C4 106.89(12) C2 C3 C4 109.38(12) C11 C3 C4 110.21(11) C3 O1 HA 103.8(17) C5 C4 C10 119.09(14) C5 C4 C3 121.53(13) C10 C4 C3 119.38(13) C4 C5 C6 120.15(15) C4 C5 H5 121.1(12) C6 C5 H5 118.8(12) C7 C6 C5 121.34(15) C7 C6 H6 118.3(12) C5 C6 H6 120.3(12) C6 C7 C9 117.91(14) C6 C7 C8 121.42(15) C9 C7 C8 120.66(15) C7 C8 H8A 113.0(16) C7 C8 H8B 113.1(18) H8A C8 H8B 109(2) C7 C8 H8C 111.0(16) H8A C8 H8C 105(2) H8B C8 H8C 105(2) C10 C9 C7 121.05(15) C10 C9 H9 118.2(11) C7 C9 H9 120.7(11) C9 C10 C4 120.45(15) C9 C10 H10 119.2(12) C4 C10 H10 120.3(12) C17 C11 C12 118.62(14) C17 C11 C3 122.77(13) C12 C11 C3 118.59(13) C13 C12 C11 120.51(14) C13 C12 H12 120.2(11) C11 C12 H12 119.3(11) C12 C13 C14 121.45(14) C12 C13 H13 118.9(13) C14 C13 H13 119.7(13) C13 C14 C16 117.71(14) C13 C14 C15 121.28(15) C16 C14 C15 121.01(15) C14 C15 H15A 111(3) C14 C15 H66 112(2) H15A C15 H66 61(3) C14 C15 H15B 114.0(19) H15A C15 H15B 129(3) H66 C15 H15B 81(3) C14 C15 H15C 111.2(19) H15A C15 H15C 82(3) H66 C15 H15C 130(3) H15B C15 H15C 102(3) C14 C16 C17 121.30(14) C14 C16 H16 121.2(11) C17 C16 H16 117.5(11) C11 C17 C16 120.41(14) C11 C17 H17 119.9(11) C16 C17 H17 119.7(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.187(2) C1 H1 0.95(2) C2 C3 1.489(2) C3 O1 1.4349(18) C3 C11 1.540(2) C3 C4 1.544(2) O1 HA 0.85(3) C4 C5 1.389(2) C4 C10 1.395(2) C5 C6 1.400(2) C5 H5 0.98(2) C6 C7 1.395(2) C6 H6 0.99(2) C7 C9 1.397(2) C7 C8 1.511(2) C8 H8A 0.99(3) C8 H8B 0.98(3) C8 H8C 0.99(3) C9 C10 1.395(2) C9 H9 0.97(2) C10 H10 1.00(2) C11 C17 1.394(2) C11 C12 1.401(2) C12 C13 1.391(2) C12 H12 0.97(2) C13 C14 1.396(2) C13 H13 0.95(2) C14 C16 1.399(2) C14 C15 1.511(2) C15 H15A 0.98(4) C15 H66 1.04(5) C15 H15B 0.94(3) C15 H15C 0.97(3) C16 C17 1.399(2) C16 H16 0.965(19) C17 H17 0.974(18) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 HA C11 0.85(3) 3.07(3) 3.860(2) 155(2) 2_655 O1 HA C13 0.85(3) 2.85(3) 3.644(2) 156(2) 2_655 O1 HA C16 0.85(3) 2.61(3) 3.288(2) 137(2) 2_655 _journal_paper_doi 10.1107/S010876810001154X