#------------------------------------------------------------------------------ #$Date: 2012-02-26 21:34:47 +0000 (Sun, 26 Feb 2012) $ #$Revision: 35909 $ #$URL: svn://www.crystallography.net/cod/cif/7/05/12/7051248.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_7051248 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 'C18 H12 O2' _chemical_formula_sum 'C18 H12 O2' _chemical_formula_weight 260.28 _chemical_melting_point 479.5(5) _chemical_name_common ; trans-9,10-Diethynyl-9,10-dihydroxy-9,10-dihydroanthracene ; _chemical_name_systematic ; trans-9,10-Diethynyl-9,10-dihydroxy-9,10-dihydroanthracene ; _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 113.78(3) _cell_angle_beta 102.06(3) _cell_angle_gamma 102.59(3) _cell_formula_units_Z 2 _cell_length_a 8.7684(18) _cell_length_b 8.9558(18) _cell_length_c 10.315(2) _cell_measurement_reflns_used 440 _cell_measurement_temperature 150 _cell_measurement_theta_max 26.23 _cell_measurement_theta_min 5.78 _cell_volume 682.3(4) _computing_cell_refinement 'Brucker SMART' _computing_data_collection 'Brucker SMART' _computing_data_reduction 'Brucker 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_measured_fraction_theta_full 0.880 _diffrn_measured_fraction_theta_max 0.880 _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 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6577 _diffrn_reflns_theta_full 30.38 _diffrn_reflns_theta_max 30.38 _diffrn_reflns_theta_min 2.29 _diffrn_standards_number 'not relevant' _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 0.4119 _exptl_absorpt_correction_T_min 0.3520 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'empirical correction using psi-scans' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 272 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.396 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 3623 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.0973 _refine_ls_R_factor_gt 0.0540 _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^)+(0.0368P)^2^+0.5022P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1084 _refine_ls_wR_factor_ref 0.1330 _reflns_number_gt 2404 _reflns_number_total 3623 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file a908233f.txt _[local]_cod_data_source_block 3 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '479-480 K' was changed to '479.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana ; _cod_original_cell_volume 682.2(2) _cod_database_code 7051248 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 _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2626(3) -0.2681(3) 0.0455(3) 0.0338(5) Uani 1 1 d . . . H1 H 0.290(3) -0.363(3) 0.046(3) 0.048(7) Uiso 1 1 d . . . C2 C 0.3852(3) -0.1105(3) 0.0951(2) 0.0304(5) Uani 1 1 d . . . H2 H 0.500(3) -0.100(3) 0.127(3) 0.035(6) Uiso 1 1 d . . . C3 C 0.3410(2) 0.0283(3) 0.0941(2) 0.0256(4) Uani 1 1 d . . . H3 H 0.427(3) 0.140(3) 0.130(3) 0.034(6) Uiso 1 1 d . . . C4 C 0.1736(2) 0.0129(2) 0.04628(19) 0.0186(4) Uani 1 1 d . . . C5 C 0.1330(2) 0.1706(2) 0.0485(2) 0.0190(4) Uani 1 1 d . . . O1 O 0.21482(17) 0.31803(17) 0.19720(15) 0.0275(3) Uani 1 1 d . . . HA H 0.194(4) 0.276(4) 0.269(4) 0.087(11) Uiso 1 1 d . . . C6 C 0.2069(2) 0.2237(2) -0.0505(2) 0.0249(4) Uani 1 1 d . . . C7 C 0.2679(3) 0.2669(3) -0.1283(3) 0.0334(5) Uani 1 1 d . . . H7 H 0.317(3) 0.304(3) -0.195(3) 0.053(8) Uiso 1 1 d . . . C8 C -0.0513(2) 0.1439(2) 0.0007(2) 0.0197(4) Uani 1 1 d . . . C9 C -0.0974(3) 0.2856(3) 0.0023(2) 0.0282(4) Uani 1 1 d . . . H9 H -0.006(3) 0.396(3) 0.043(3) 0.035(6) Uiso 1 1 d . . . C21 C 0.8055(3) 0.2958(3) 0.3612(3) 0.0363(5) Uani 1 1 d . . . H21 H 0.889(3) 0.274(3) 0.314(3) 0.048(7) Uiso 1 1 d . . . C22 C 0.7475(3) 0.4286(3) 0.3655(2) 0.0301(4) Uani 1 1 d . . . H22 H 0.791(3) 0.500(3) 0.320(3) 0.034(6) Uiso 1 1 d . . . C23 C 0.6262(2) 0.4628(2) 0.4319(2) 0.0206(4) Uani 1 1 d . . . C24 C 0.5697(2) 0.6133(2) 0.4337(2) 0.0205(4) Uani 1 1 d . . . O2 O 0.51293(18) 0.59111(18) 0.28344(15) 0.0262(3) Uani 1 1 d . . . HB H 0.418(4) 0.502(4) 0.234(3) 0.058(8) Uiso 1 1 d . . . C25 C 0.7171(2) 0.7758(2) 0.5189(2) 0.0246(4) Uani 1 1 d . . . C26 C 0.8354(3) 0.9037(3) 0.5925(2) 0.0332(5) Uani 1 1 d . . . H26 H 0.931(3) 1.003(3) 0.652(3) 0.044(7) Uiso 1 1 d . . . C27 C 0.4359(2) 0.6393(2) 0.5062(2) 0.0206(4) Uani 1 1 d . . . C28 C 0.3738(3) 0.7721(3) 0.5092(2) 0.0292(4) Uani 1 1 d . . . H28 H 0.416(3) 0.840(3) 0.462(3) 0.039(6) Uiso 1 1 d . . . C29 C 0.2540(3) 0.8040(3) 0.5739(3) 0.0357(5) Uani 1 1 d . . . H29 H 0.210(3) 0.896(3) 0.575(3) 0.043(7) 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 0.0370(12) 0.0332(11) 0.0436(13) 0.0243(10) 0.0150(10) 0.0206(10) C2 0.0229(10) 0.0411(12) 0.0342(11) 0.0197(10) 0.0107(9) 0.0183(9) C3 0.0178(9) 0.0294(10) 0.0269(10) 0.0117(8) 0.0082(8) 0.0056(8) C4 0.0201(9) 0.0208(9) 0.0179(8) 0.0104(7) 0.0090(7) 0.0069(7) C5 0.0187(8) 0.0169(8) 0.0191(8) 0.0082(7) 0.0061(7) 0.0023(7) O1 0.0285(7) 0.0220(7) 0.0230(7) 0.0066(6) 0.0049(6) 0.0032(6) C6 0.0234(10) 0.0235(9) 0.0282(10) 0.0133(8) 0.0082(8) 0.0066(8) C7 0.0369(12) 0.0368(12) 0.0427(13) 0.0271(10) 0.0226(10) 0.0164(10) C8 0.0198(9) 0.0213(9) 0.0227(9) 0.0133(7) 0.0098(7) 0.0072(7) C9 0.0294(11) 0.0238(10) 0.0374(12) 0.0185(9) 0.0126(9) 0.0104(8) C21 0.0322(12) 0.0404(12) 0.0397(13) 0.0165(10) 0.0184(10) 0.0168(10) C22 0.0263(10) 0.0353(11) 0.0316(11) 0.0173(9) 0.0149(9) 0.0077(9) C23 0.0195(9) 0.0204(9) 0.0192(9) 0.0087(7) 0.0058(7) 0.0036(7) C24 0.0209(9) 0.0234(9) 0.0193(9) 0.0133(7) 0.0073(7) 0.0043(7) O2 0.0263(7) 0.0299(7) 0.0208(7) 0.0160(6) 0.0051(6) 0.0012(6) C25 0.0255(10) 0.0277(10) 0.0234(9) 0.0158(8) 0.0084(8) 0.0062(8) C26 0.0310(11) 0.0320(11) 0.0307(11) 0.0166(9) 0.0058(9) 0.0005(9) C27 0.0205(9) 0.0211(9) 0.0187(9) 0.0095(7) 0.0060(7) 0.0043(7) C28 0.0317(11) 0.0272(10) 0.0315(11) 0.0167(9) 0.0103(9) 0.0099(9) C29 0.0339(12) 0.0326(11) 0.0418(13) 0.0159(10) 0.0118(10) 0.0174(10) 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 C9 C1 C2 120.27(19) 2 . yes C9 C1 H1 118.9(16) 2 . yes C2 C1 H1 120.8(16) . . yes C3 C2 C1 119.74(19) . . yes C3 C2 H2 120.5(14) . . yes C1 C2 H2 119.7(14) . . yes C2 C3 C4 120.72(19) . . yes C2 C3 H3 120.0(13) . . yes C4 C3 H3 119.3(13) . . yes C8 C4 C3 119.44(17) 2 . yes C8 C4 C5 122.36(15) 2 . yes C3 C4 C5 118.20(16) . . yes O1 C5 C6 104.47(14) . . yes O1 C5 C8 109.21(15) . . yes C6 C5 C8 108.97(15) . . yes O1 C5 C4 109.89(14) . . yes C6 C5 C4 109.36(15) . . yes C8 C5 C4 114.46(14) . . yes C5 O1 HA 107(2) . . yes C7 C6 C5 179.2(2) . . yes C6 C7 H7 178.8(15) . . yes C4 C8 C9 119.44(17) 2 . yes C4 C8 C5 123.15(15) 2 . yes C9 C8 C5 117.40(16) . . yes C1 C9 C8 120.37(19) 2 . yes C1 C9 H9 123.3(13) 2 . yes C8 C9 H9 116.3(13) . . yes C22 C21 C29 120.0(2) . 2_666 yes C22 C21 H21 119.6(15) . . yes C29 C21 H21 120.4(15) 2_666 . yes C21 C22 C23 120.87(19) . . yes C21 C22 H22 119.5(13) . . yes C23 C22 H22 119.7(13) . . yes C27 C23 C22 119.18(17) 2_666 . yes C27 C23 C24 123.08(16) 2_666 . yes C22 C23 C24 117.73(16) . . yes O2 C24 C25 105.98(14) . . yes O2 C24 C27 109.72(14) . . yes C25 C24 C27 108.40(15) . . yes O2 C24 C23 110.19(15) . . yes C25 C24 C23 108.16(15) . . yes C27 C24 C23 114.05(14) . . yes C24 O2 HB 107.2(18) . . yes C26 C25 C24 176.9(2) . . yes C25 C26 H26 178.0(16) . . yes C23 C27 C28 119.31(17) 2_666 . yes C23 C27 C24 122.85(16) 2_666 . yes C28 C27 C24 117.84(16) . . yes C29 C28 C27 121.03(19) . . yes C29 C28 H28 120.8(14) . . yes C27 C28 H28 118.2(14) . . yes C28 C29 C21 119.6(2) . 2_666 yes C28 C29 H29 121.0(14) . . yes C21 C29 H29 119.4(14) 2_666 . 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 C9 1.381(3) 2 yes C1 C2 1.391(3) . yes C1 H1 0.94(3) . yes C2 C3 1.383(3) . yes C2 H2 0.96(2) . yes C3 C4 1.404(3) . yes C3 H3 0.98(2) . yes C4 C8 1.391(2) 2 yes C4 C5 1.523(2) . yes C5 O1 1.450(2) . yes C5 C6 1.491(3) . yes C5 C8 1.522(2) . yes O1 HA 0.99(3) . yes C6 C7 1.191(3) . yes C7 H7 1.01(3) . yes C8 C4 1.391(2) 2 yes C8 C9 1.408(3) . yes C9 C1 1.381(3) 2 yes C9 H9 0.99(2) . yes C21 C22 1.380(3) . yes C21 C29 1.394(3) 2_666 yes C21 H21 0.97(3) . yes C22 C23 1.404(3) . yes C22 H22 0.99(2) . yes C23 C27 1.393(2) 2_666 yes C23 C24 1.529(3) . yes C24 O2 1.440(2) . yes C24 C25 1.494(3) . yes C24 C27 1.529(3) . yes O2 HB 0.89(3) . yes C25 C26 1.190(3) . yes C26 H26 0.94(3) . yes C27 C23 1.393(2) 2_666 yes C27 C28 1.403(3) . yes C28 C29 1.379(3) . yes C28 H28 0.98(2) . yes C29 C21 1.394(3) 2_666 yes C29 H29 0.98(2) . yes