#------------------------------------------------------------------------------ #$Date: 2014-07-12 05:06:18 +0100 (Sat, 12 Jul 2014) $ #$Revision: 120112 $ #$URL: svn://www.crystallography.net/cod/cif/7/05/12/7051249.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7051249 loop_ _publ_author_name 'Laxmi Madhavi, N. N.' 'Bilton, Clair' 'Howard, Judith A. K.' 'Allen, Frank H.' 'Nangia, Ashwini' 'Desiraju, Gautam R.' _publ_section_title ; Seeking structural repetitivity in systems with interaction interference: crystal engineering in the gem-alkynol family ; _journal_issue 1 _journal_name_full 'New Journal of Chemistry' _journal_page_first 1 _journal_volume 24 _journal_year 2000 _chemical_formula_moiety 'C14 H10 O2' _chemical_formula_sum 'C14 H10 O2' _chemical_formula_weight 210.22 _chemical_melting_point 407 _chemical_name_common ; trans-1,4-Diethynyl-1,4-dihydroxy-1,4-dihydronaphthalene ; _chemical_name_systematic ; trans-1,4-Diethynyl-1,4-dihydroxy-1,4-dihydronaphthalene ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 118.1850(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 10.8247(3) _cell_length_b 22.6384(8) _cell_length_c 10.4783(3) _cell_measurement_reflns_used 935 _cell_measurement_temperature 150 _cell_measurement_theta_max 23.24 _cell_measurement_theta_min 5.18 _cell_volume 2263.28(12) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'SHELXS-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150 _diffrn_detector_area_resol_mean 'not relevant' _diffrn_measured_fraction_theta_full 0.905 _diffrn_measured_fraction_theta_max 0.905 _diffrn_measurement_device_type 'Brucker SMART CCD' _diffrn_measurement_method '/w scans' _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 0.0628 _diffrn_reflns_av_sigmaI/netI 0.0654 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 17967 _diffrn_reflns_theta_full 30.33 _diffrn_reflns_theta_max 30.33 _diffrn_reflns_theta_min 1.80 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 0.6141 _exptl_absorpt_correction_T_min 0.3984 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'empirical correction using psi-scans' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.342 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 369 _refine_ls_number_reflns 6159 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.983 _refine_ls_R_factor_all 0.1083 _refine_ls_R_factor_gt 0.0596 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0897P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1401 _refine_ls_wR_factor_ref 0.1597 _reflns_number_gt 3713 _reflns_number_total 6159 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file a908233f.txt _[local]_cod_data_source_block 6 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '407 K' was changed to '407' - the value should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana ; _cod_database_code 7051249 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6057(2) 0.16584(9) 0.0655(2) 0.0358(5) Uani 1 1 d . . . H1 H 0.703(2) 0.1669(8) 0.105(2) 0.028(5) Uiso 1 1 d . . . C2 C 0.48196(19) 0.16350(8) 0.01449(19) 0.0278(4) Uani 1 1 d . . . C3 C 0.32622(18) 0.16012(8) -0.05833(17) 0.0237(4) Uani 1 1 d . . . O1 O 0.28541(14) 0.17313(6) 0.05084(13) 0.0305(3) Uani 1 1 d . . . H1A H 0.192(2) 0.1761(8) 0.008(2) 0.031(5) Uiso 1 1 d . . . C4 C 0.28267(17) 0.09749(8) -0.11667(17) 0.0229(4) Uani 1 1 d . . . C5 C 0.3303(2) 0.05028(8) -0.0182(2) 0.0317(4) Uani 1 1 d . . . H5 H 0.387(2) 0.0605(9) 0.086(2) 0.036(5) Uiso 1 1 d . . . C6 C 0.2980(2) -0.00698(9) -0.0650(2) 0.0390(5) Uani 1 1 d . . . H6 H 0.339(2) -0.0405(9) 0.004(3) 0.041(6) Uiso 1 1 d . . . C7 C 0.2183(2) -0.01898(9) -0.2132(2) 0.0397(5) Uani 1 1 d . . . H7 H 0.198(2) -0.0609(11) -0.241(3) 0.050(7) Uiso 1 1 d . . . C8 C 0.1701(2) 0.02680(9) -0.3109(2) 0.0330(4) Uani 1 1 d . . . H8 H 0.112(2) 0.0179(9) -0.413(3) 0.039(6) Uiso 1 1 d . . . C9 C 0.19988(17) 0.08572(7) -0.26428(17) 0.0229(4) Uani 1 1 d . . . C10 C 0.13988(18) 0.13488(8) -0.37732(17) 0.0249(4) Uani 1 1 d . . . C11 C -0.01601(19) 0.13251(8) -0.44756(18) 0.0288(4) Uani 1 1 d . . . C12 C -0.1393(2) 0.13167(9) -0.4965(2) 0.0365(5) Uani 1 1 d . . . H12 H -0.238(3) 0.1306(10) -0.533(3) 0.047(7) Uiso 1 1 d . . . O2 O 0.17743(15) 0.12550(6) -0.49066(13) 0.0327(3) Uani 1 1 d . . . H1B H 0.276(3) 0.1259(10) -0.448(3) 0.054(7) Uiso 1 1 d . . . C13 C 0.18568(19) 0.19571(8) -0.31458(19) 0.0281(4) Uani 1 1 d . . . H13 H 0.149(2) 0.2288(10) -0.382(3) 0.048(6) Uiso 1 1 d . . . C14 C 0.26793(19) 0.20682(8) -0.17528(19) 0.0275(4) Uani 1 1 d . . . H14 H 0.2925(19) 0.2480(9) -0.146(2) 0.027(5) Uiso 1 1 d . . . C21 C 0.0004(2) 0.15781(10) 0.1815(2) 0.0379(5) Uani 1 1 d . . . H21 H 0.044(3) 0.1561(11) 0.293(3) 0.068(8) Uiso 1 1 d . . . C22 C -0.05315(18) 0.16146(8) 0.05225(19) 0.0282(4) Uani 1 1 d . . . C23 C -0.11749(17) 0.16598(8) -0.10767(18) 0.0248(4) Uani 1 1 d . . . O21 O -0.00582(14) 0.18835(6) -0.13431(15) 0.0325(3) Uani 1 1 d . . . H2A H -0.036(3) 0.1888(14) -0.230(4) 0.090(10) Uiso 1 1 d . . . C24 C -0.16527(17) 0.10569(8) -0.17697(17) 0.0234(4) Uani 1 1 d . . . C25 C -0.0664(2) 0.06005(9) -0.1399(2) 0.0312(4) Uani 1 1 d . . . H25 H 0.032(2) 0.0682(9) -0.079(2) 0.036(6) Uiso 1 1 d . . . C26 C -0.1044(2) 0.00488(9) -0.2001(2) 0.0384(5) Uani 1 1 d . . . H26 H -0.039(3) -0.0254(10) -0.178(3) 0.045(6) Uiso 1 1 d . . . C27 C -0.2444(2) -0.00721(10) -0.2976(2) 0.0413(5) Uani 1 1 d . . . H27 H -0.267(2) -0.0479(10) -0.337(3) 0.045(6) Uiso 1 1 d . . . C28 C -0.3427(2) 0.03720(9) -0.3345(2) 0.0360(5) Uani 1 1 d . . . H28 H -0.442(3) 0.0287(10) -0.397(3) 0.052(7) Uiso 1 1 d . . . C29 C -0.30452(18) 0.09391(8) -0.27648(18) 0.0251(4) Uani 1 1 d . . . C30 C -0.41771(18) 0.14099(8) -0.32551(18) 0.0262(4) Uani 1 1 d . . . C31 C -0.48351(19) 0.14777(9) -0.48569(19) 0.0300(4) Uani 1 1 d . . . C32 C -0.5363(2) 0.15364(10) -0.6138(2) 0.0382(5) Uani 1 1 d . . . H32 H -0.582(3) 0.1582(13) -0.720(4) 0.084(9) Uiso 1 1 d . . . O22 O -0.53108(14) 0.12168(7) -0.29872(16) 0.0354(3) Uani 1 1 d . . . H2B H -0.500(3) 0.1227(12) -0.214(3) 0.065(9) Uiso 1 1 d . . . C33 C -0.3652(2) 0.20015(9) -0.25591(19) 0.0293(4) Uani 1 1 d . . . H33 H -0.436(2) 0.2292(10) -0.285(2) 0.042(6) Uiso 1 1 d . . . C34 C -0.2337(2) 0.21101(8) -0.15949(19) 0.0285(4) Uani 1 1 d . . . H34 H -0.208(2) 0.2508(10) -0.123(3) 0.046(6) 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 0.0271(10) 0.0463(12) 0.0301(10) -0.0069(8) 0.0103(8) -0.0026(8) C2 0.0315(10) 0.0308(10) 0.0195(8) -0.0043(7) 0.0109(7) 0.0003(7) C3 0.0254(9) 0.0316(9) 0.0151(8) -0.0025(6) 0.0105(7) 0.0008(7) O1 0.0276(7) 0.0480(8) 0.0154(6) -0.0054(5) 0.0097(5) 0.0047(6) C4 0.0213(8) 0.0301(9) 0.0165(8) 0.0001(6) 0.0083(7) 0.0009(7) C5 0.0328(10) 0.0371(11) 0.0227(9) 0.0050(8) 0.0110(8) 0.0037(8) C6 0.0400(12) 0.0349(11) 0.0399(12) 0.0115(9) 0.0170(10) 0.0056(9) C7 0.0411(12) 0.0287(11) 0.0457(12) -0.0040(9) 0.0177(10) -0.0025(8) C8 0.0328(10) 0.0360(11) 0.0273(10) -0.0085(8) 0.0117(8) -0.0035(8) C9 0.0209(8) 0.0306(9) 0.0170(7) -0.0008(6) 0.0087(7) -0.0004(7) C10 0.0251(9) 0.0366(10) 0.0119(7) 0.0015(7) 0.0079(7) 0.0017(7) C11 0.0288(10) 0.0401(11) 0.0167(8) 0.0029(7) 0.0102(7) 0.0013(8) C12 0.0298(11) 0.0525(13) 0.0253(10) 0.0041(8) 0.0114(9) 0.0023(9) O2 0.0266(7) 0.0588(9) 0.0137(6) -0.0003(5) 0.0103(5) 0.0012(6) C13 0.0298(10) 0.0306(10) 0.0241(9) 0.0076(7) 0.0129(8) 0.0024(7) C14 0.0297(10) 0.0255(9) 0.0247(9) 0.0002(7) 0.0108(8) -0.0001(7) C21 0.0372(11) 0.0505(13) 0.0206(9) 0.0001(8) 0.0093(8) -0.0048(9) C22 0.0247(9) 0.0362(10) 0.0201(8) 0.0000(7) 0.0077(7) -0.0035(7) C23 0.0218(8) 0.0352(10) 0.0168(8) 0.0016(7) 0.0085(7) -0.0028(7) O21 0.0285(7) 0.0470(8) 0.0231(7) 0.0039(6) 0.0131(6) -0.0070(6) C24 0.0239(9) 0.0311(9) 0.0151(7) 0.0049(6) 0.0091(7) 0.0015(7) C25 0.0275(10) 0.0411(11) 0.0250(9) 0.0078(8) 0.0124(8) 0.0040(8) C26 0.0474(13) 0.0352(11) 0.0367(11) 0.0095(9) 0.0233(10) 0.0119(9) C27 0.0569(14) 0.0325(11) 0.0358(11) -0.0042(9) 0.0228(10) 0.0001(10) C28 0.0383(11) 0.0388(11) 0.0260(10) -0.0047(8) 0.0110(9) -0.0028(9) C29 0.0263(9) 0.0328(9) 0.0161(8) 0.0008(7) 0.0099(7) 0.0007(7) C30 0.0205(8) 0.0402(10) 0.0158(8) 0.0008(7) 0.0069(7) 0.0005(7) C31 0.0244(9) 0.0423(11) 0.0201(8) 0.0000(7) 0.0079(7) 0.0036(7) C32 0.0371(11) 0.0539(13) 0.0205(9) 0.0026(9) 0.0110(8) 0.0087(9) O22 0.0246(7) 0.0601(10) 0.0213(7) -0.0005(6) 0.0108(6) -0.0028(6) C33 0.0306(10) 0.0349(10) 0.0202(8) 0.0026(7) 0.0103(7) 0.0071(8) C34 0.0350(10) 0.0288(10) 0.0212(8) 0.0004(7) 0.0129(8) 0.0004(7) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C2 C3 176.53(19) . . yes O1 C3 C2 106.31(13) . . yes O1 C3 C14 109.52(14) . . yes C2 C3 C14 108.51(15) . . yes O1 C3 C4 110.83(14) . . yes C2 C3 C4 108.27(14) . . yes C14 C3 C4 113.13(14) . . yes C9 C4 C5 119.27(16) . . yes C9 C4 C3 122.32(15) . . yes C5 C4 C3 118.40(15) . . yes C6 C5 C4 120.91(18) . . yes C5 C6 C7 119.93(18) . . yes C8 C7 C6 119.83(19) . . yes C7 C8 C9 120.87(18) . . yes C4 C9 C8 119.15(16) . . yes C4 C9 C10 122.27(15) . . yes C8 C9 C10 118.58(16) . . yes O2 C10 C11 106.39(13) . . yes O2 C10 C13 109.37(14) . . yes C11 C10 C13 108.13(15) . . yes O2 C10 C9 110.45(14) . . yes C11 C10 C9 108.92(14) . . yes C13 C10 C9 113.32(14) . . yes C12 C11 C10 176.43(19) . . yes C14 C13 C10 124.44(16) . . yes C13 C14 C3 124.44(16) . . yes C21 C22 C23 179.2(2) . . yes O21 C23 C22 104.57(13) . . yes O21 C23 C34 108.87(14) . . yes C22 C23 C34 108.68(15) . . yes O21 C23 C24 110.35(14) . . yes C22 C23 C24 110.52(14) . . yes C34 C23 C24 113.46(14) . . yes C29 C24 C25 118.65(17) . . yes C29 C24 C23 122.24(15) . . yes C25 C24 C23 119.11(16) . . yes C26 C25 C24 121.25(19) . . yes C25 C26 C27 120.04(19) . . yes C28 C27 C26 119.2(2) . . yes C27 C28 C29 121.2(2) . . yes C24 C29 C28 119.62(17) . . yes C24 C29 C30 122.20(16) . . yes C28 C29 C30 118.17(16) . . yes O22 C30 C31 104.56(14) . . yes O22 C30 C33 109.59(15) . . yes C31 C30 C33 108.96(15) . . yes O22 C30 C29 110.15(15) . . yes C31 C30 C29 109.48(15) . . yes C33 C30 C29 113.69(14) . . yes C32 C31 C30 179.5(2) . . yes C34 C33 C30 124.07(17) . . yes C33 C34 C23 124.31(17) . . yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.185(3) . yes C2 C3 1.488(2) . yes C3 O1 1.438(2) . yes C3 C14 1.512(2) . yes C3 C4 1.528(2) . yes C4 C9 1.399(2) . yes C4 C5 1.404(2) . yes C5 C6 1.371(3) . yes C6 C7 1.401(3) . yes C7 C8 1.374(3) . yes C8 C9 1.405(3) . yes C9 C10 1.529(2) . yes C10 O2 1.441(2) . yes C10 C11 1.490(2) . yes C10 C13 1.505(3) . yes C11 C12 1.183(3) . yes C13 C14 1.326(2) . yes C21 C22 1.198(3) . yes C22 C23 1.484(2) . yes C23 O21 1.454(2) . yes C23 C34 1.507(3) . yes C23 C24 1.518(2) . yes C24 C29 1.395(2) . yes C24 C25 1.404(3) . yes C25 C26 1.372(3) . yes C26 C27 1.397(3) . yes C27 C28 1.380(3) . yes C28 C29 1.397(3) . yes C29 C30 1.519(2) . yes C30 O22 1.450(2) . yes C30 C31 1.490(2) . yes C30 C33 1.502(3) . yes C31 C32 1.192(3) . yes C33 C34 1.323(3) . yes _journal_paper_doi 10.1039/a908233f