#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/77/1507754.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_1507754 loop_ _publ_author_name 'Liu, Jiawang' 'Nguyen, Thong T.' 'Dupart, Patrick S.' 'Sridhar, Jayalakshmi' 'Zhang, Xiaoyi' 'Zhu, Naijue' 'Stevens, Cheryl L Klein' 'Foroozesh, Maryam' _publ_section_title ; 7-Ethynylcoumarins: Selective Inhibitors of Human Cytochrome P450s 1A1 and 1A2. ; _journal_issue 5 _journal_name_full 'Chemical research in toxicology' _journal_page_first 1047 _journal_page_last 1057 _journal_paper_doi 10.1021/tx300023p _journal_volume 25 _journal_year 2012 _chemical_formula_sum 'C18 H12 O2' _chemical_formula_weight 260.28 _chemical_name_common 7-ethynylcoumarin _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 104.050(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.8113(10) _cell_length_b 10.3682(12) _cell_length_c 14.2027(18) _cell_measurement_reflns_used 2437 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 24.31 _cell_measurement_theta_min 2.45 _cell_volume 1401.6(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Platon (v-290610)' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker SMART X2S' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_radiation_source 'microfocus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 8163 _diffrn_reflns_theta_full 24.98 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_min 2.29 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_correction_T_min 0.9331 _exptl_absorpt_correction_type empirical _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.88 _exptl_crystal_size_mid 0.88 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.159 _refine_diff_density_min -0.112 _refine_diff_density_rms 0.031 _refine_ls_extinction_coef 0.057(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 183 _refine_ls_number_reflns 2434 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.022 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0396 _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^)+(0.0666P)^2^+0.1033P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1078 _refine_ls_wR_factor_ref 0.1230 _reflns_number_gt 1654 _reflns_number_total 2434 _reflns_threshold_expression >2sigma(I) _cod_data_source_file tx300023p_si_001.cif _cod_data_source_block scan_0m_p21_n _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M P2(1)/n _cod_database_code 1507754 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 O1 O 1.12963(11) 0.01447(10) 0.19294(9) 0.0623(3) Uani 1 1 d . O2 O 1.25784(12) 0.14869(12) 0.29683(11) 0.0842(4) Uani 1 1 d . C15 C 0.5237(2) 0.3998(3) 0.13319(17) 0.0876(7) Uani 1 1 d . H15 H 0.4399 0.4496 0.1197 0.105 Uiso 1 1 calc R C14 C 0.52860(19) 0.2861(2) 0.18292(15) 0.0833(6) Uani 1 1 d . H14 H 0.4495 0.2583 0.2051 0.100 Uiso 1 1 calc R C13 C 0.65029(18) 0.21127(19) 0.20091(14) 0.0717(5) Uani 1 1 d . H13 H 0.6542 0.1324 0.2355 0.086 Uiso 1 1 calc R C12 C 0.76508(16) 0.25171(16) 0.16859(12) 0.0591(4) Uani 1 1 d . C3 C 0.89382(16) 0.16996(15) 0.18128(12) 0.0565(4) Uani 1 1 d . C4 C 0.88366(15) 0.05167(15) 0.12528(11) 0.0532(4) Uani 1 1 d . C9 C 1.00315(15) -0.02378(15) 0.13381(11) 0.0527(4) Uani 1 1 d . C8 C 1.00268(17) -0.13918(15) 0.08537(12) 0.0574(4) Uani 1 1 d . H8 H 1.0865 -0.1882 0.0936 0.069 Uiso 1 1 calc R C7 C 0.87900(16) -0.18276(15) 0.02482(12) 0.0578(4) Uani 1 1 d . C10 C 0.87423(17) -0.30352(18) -0.02563(13) 0.0661(5) Uani 1 1 d . C11 C 0.86828(19) -0.4027(2) -0.06767(16) 0.0798(6) Uani 1 1 d . H11 H 0.8635 -0.4823 -0.1014 0.096 Uiso 1 1 calc R C1 C 1.14210(17) 0.12540(16) 0.24713(13) 0.0625(5) Uani 1 1 d . C2 C 1.01800(17) 0.20428(16) 0.24141(13) 0.0620(5) Uani 1 1 d . C18 C 1.0399(2) 0.32061(18) 0.30627(16) 0.0886(7) Uani 1 1 d . H18A H 1.1027 0.3814 0.2849 0.133 Uiso 1 1 calc R H18B H 1.0820 0.2940 0.3732 0.133 Uiso 1 1 calc R H18C H 0.9493 0.3624 0.3030 0.133 Uiso 1 1 calc R C6 C 0.75715(18) -0.10811(17) 0.01339(13) 0.0665(5) Uani 1 1 d . H6 H 0.6717 -0.1371 -0.0283 0.080 Uiso 1 1 calc R C5 C 0.76020(17) 0.00666(17) 0.06196(13) 0.0636(5) Uani 1 1 d . H5 H 0.6769 0.0567 0.0525 0.076 Uiso 1 1 calc R C17 C 0.75830(18) 0.36834(17) 0.12003(14) 0.0719(5) Uani 1 1 d . H17 H 0.8373 0.3976 0.0984 0.086 Uiso 1 1 calc R C16 C 0.6374(2) 0.4427(2) 0.10278(16) 0.0861(6) Uani 1 1 d . H16 H 0.6337 0.5230 0.0700 0.103 Uiso 1 1 calc R 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 O1 0.0413(6) 0.0671(7) 0.0713(8) 0.0085(6) -0.0003(5) 0.0001(5) O2 0.0497(8) 0.0775(8) 0.1071(10) 0.0066(7) -0.0164(7) -0.0080(6) C15 0.0596(13) 0.1143(18) 0.0819(14) -0.0266(13) 0.0036(11) 0.0223(12) C14 0.0530(12) 0.1222(18) 0.0775(13) -0.0363(13) 0.0211(10) -0.0107(11) C13 0.0594(11) 0.0863(12) 0.0703(11) -0.0111(10) 0.0172(9) -0.0090(9) C12 0.0450(9) 0.0692(11) 0.0608(10) -0.0060(8) 0.0081(7) 0.0000(8) C3 0.0450(9) 0.0626(9) 0.0595(10) 0.0085(8) 0.0083(8) -0.0013(7) C4 0.0414(9) 0.0628(9) 0.0529(9) 0.0089(7) 0.0066(7) -0.0005(7) C9 0.0404(9) 0.0620(10) 0.0518(9) 0.0111(8) 0.0037(7) -0.0017(7) C8 0.0464(9) 0.0639(10) 0.0611(10) 0.0115(8) 0.0113(8) 0.0057(7) C7 0.0503(10) 0.0651(10) 0.0570(10) 0.0021(8) 0.0111(8) -0.0009(8) C10 0.0517(10) 0.0765(12) 0.0684(11) -0.0005(10) 0.0112(9) -0.0011(9) C11 0.0623(12) 0.0823(13) 0.0919(14) -0.0144(12) 0.0133(10) -0.0009(10) C1 0.0486(10) 0.0606(10) 0.0704(11) 0.0127(9) -0.0008(8) -0.0068(8) C2 0.0487(10) 0.0630(10) 0.0686(11) 0.0051(8) 0.0033(8) -0.0045(8) C18 0.0707(13) 0.0834(13) 0.0996(16) -0.0184(12) -0.0027(12) -0.0062(10) C6 0.0480(10) 0.0814(12) 0.0650(11) -0.0083(9) 0.0035(8) -0.0015(9) C5 0.0417(9) 0.0788(11) 0.0661(11) -0.0027(9) 0.0046(8) 0.0057(8) C17 0.0532(11) 0.0799(12) 0.0805(13) 0.0080(10) 0.0123(9) 0.0094(9) C16 0.0701(13) 0.0914(14) 0.0905(15) -0.0001(12) 0.0073(12) 0.0196(11) 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 C1 O1 C9 121.84(12) C16 C15 C14 121.02(19) C16 C15 H15 119.5 C14 C15 H15 119.5 C15 C14 C13 119.64(18) C15 C14 H14 120.2 C13 C14 H14 120.2 C12 C13 C14 120.1(2) C12 C13 H13 120.0 C14 C13 H13 120.0 C13 C12 C17 119.08(16) C13 C12 C3 121.41(16) C17 C12 C3 119.46(14) C2 C3 C4 119.92(15) C2 C3 C12 122.09(15) C4 C3 C12 117.98(13) C9 C4 C5 116.60(15) C9 C4 C3 118.91(14) C5 C4 C3 124.50(14) O1 C9 C8 116.57(14) O1 C9 C4 120.48(15) C8 C9 C4 122.95(14) C9 C8 C7 119.35(15) C9 C8 H8 120.3 C7 C8 H8 120.3 C8 C7 C6 119.17(15) C8 C7 C10 120.82(15) C6 C7 C10 120.00(15) C11 C10 C7 179.1(2) C10 C11 H11 180.0 O2 C1 O1 116.01(15) O2 C1 C2 125.23(17) O1 C1 C2 118.75(14) C3 C2 C1 120.05(16) C3 C2 C18 124.79(16) C1 C2 C18 115.15(15) C2 C18 H18A 109.5 C2 C18 H18B 109.5 H18A C18 H18B 109.5 C2 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 C5 C6 C7 120.48(16) C5 C6 H6 119.8 C7 C6 H6 119.8 C6 C5 C4 121.42(15) C6 C5 H5 119.3 C4 C5 H5 119.3 C12 C17 C16 120.61(18) C12 C17 H17 119.7 C16 C17 H17 119.7 C15 C16 C17 119.5(2) C15 C16 H16 120.2 C17 C16 H16 120.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.373(2) O1 C9 1.3771(18) O2 C1 1.2071(19) C15 C16 1.364(3) C15 C14 1.369(3) C15 H15 0.9500 C14 C13 1.394(3) C14 H14 0.9500 C13 C12 1.381(2) C13 H13 0.9500 C12 C17 1.386(2) C12 C3 1.495(2) C3 C2 1.355(2) C3 C4 1.452(2) C4 C9 1.390(2) C4 C5 1.402(2) C9 C8 1.380(2) C8 C7 1.382(2) C8 H8 0.9500 C7 C6 1.400(2) C7 C10 1.438(2) C10 C11 1.184(2) C11 H11 0.9500 C1 C2 1.453(2) C2 C18 1.501(2) C18 H18A 0.9800 C18 H18B 0.9800 C18 H18C 0.9800 C6 C5 1.372(2) C6 H6 0.9500 C5 H5 0.9500 C17 C16 1.386(2) C17 H17 0.9500 C16 H16 0.9500 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C16 C15 C14 C13 -1.5(3) C15 C14 C13 C12 -0.1(3) C14 C13 C12 C17 1.3(3) C14 C13 C12 C3 -176.17(16) C13 C12 C3 C2 -112.33(19) C17 C12 C3 C2 70.2(2) C13 C12 C3 C4 68.8(2) C17 C12 C3 C4 -108.60(18) C2 C3 C4 C9 -0.8(2) C12 C3 C4 C9 178.10(14) C2 C3 C4 C5 179.26(15) C12 C3 C4 C5 -1.9(2) C1 O1 C9 C8 -177.91(13) C1 O1 C9 C4 1.7(2) C5 C4 C9 O1 178.71(14) C3 C4 C9 O1 -1.3(2) C5 C4 C9 C8 -1.7(2) C3 C4 C9 C8 178.32(14) O1 C9 C8 C7 -179.91(13) C4 C9 C8 C7 0.5(2) C9 C8 C7 C6 0.5(2) C9 C8 C7 C10 -179.05(15) C8 C7 C10 C11 176(100) C6 C7 C10 C11 -3(12) C9 O1 C1 O2 179.45(14) C9 O1 C1 C2 -0.1(2) C4 C3 C2 C1 2.3(2) C12 C3 C2 C1 -176.48(15) C4 C3 C2 C18 -176.99(16) C12 C3 C2 C18 4.2(3) O2 C1 C2 C3 178.55(16) O1 C1 C2 C3 -1.9(2) O2 C1 C2 C18 -2.1(3) O1 C1 C2 C18 177.45(15) C8 C7 C6 C5 -0.3(3) C10 C7 C6 C5 179.34(16) C7 C6 C5 C4 -1.0(3) C9 C4 C5 C6 2.0(2) C3 C4 C5 C6 -178.05(16) C13 C12 C17 C16 -0.9(3) C3 C12 C17 C16 176.57(17) C14 C15 C16 C17 1.9(3) C12 C17 C16 C15 -0.6(3)