#------------------------------------------------------------------------------ #$Date: 2012-02-26 23:34:47 +0200 (Sun, 26 Feb 2012) $ #$Revision: 35909 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/17/7151735.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_7151735 loop_ _publ_author_name 'Malik, Heetika' 'Kohlen, Wouter' 'Jamil, Muhammad' 'Rutjes, Floris P. J. T.' 'Zwanenburg, Binne' _publ_section_title ; Aromatic A-ring analogues of orobanchol, new germination stimulants for seeds of parasitic weeds. ; _journal_issue 7 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 2286 _journal_page_last 2293 _journal_volume 9 _journal_year 2011 _chemical_formula_sum 'C11 H10 O3' _chemical_formula_weight 190.19 _chemical_name_systematic ; ? ; _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 geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2006-07-27 _audit_creation_method 'SHELXL, adapted and expanded' _cell_angle_alpha 90.00 _cell_angle_beta 94.165(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.3372(4) _cell_length_b 10.9310(7) _cell_length_c 9.7141(3) _cell_measurement_reflns_used 176 _cell_measurement_temperature 208(2) _cell_measurement_theta_max 27.520 _cell_measurement_theta_min 2.450 _cell_volume 882.95(8) _computing_data_collection ; Nonius "Collect" program suite (Nonius, 1999) ; _computing_data_reduction ; Nonius "EvalCCD" program suite (Duisenberg, 1998) ; _computing_molecular_graphics ; PLATON (Spek, 2003) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution ; ; _diffrn_ambient_temperature 208(2) _diffrn_detector_area_resol_mean 18.4 _diffrn_measured_fraction_theta_full 0.945 _diffrn_measured_fraction_theta_max 0.950 _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method 'area detector \f and \w scan' _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 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 20709 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_min 2.45 _diffrn_standards_decay_% 0.000 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6879 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS multiscan (Sheldrick, 1996)' _exptl_crystal_colour 'translucent colourless' _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'regular thick platelet' _exptl_crystal_F_000 400 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.231 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.098 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 128 _refine_ls_number_reflns 2028 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.098 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0429 _refine_ls_R_factor_obs 0.0429 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+0.3201P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1012 _refine_ls_wR_factor_gt 0.0959 _refine_ls_wR_factor_obs 0.0959 _refine_ls_wR_factor_ref 0.1012 _reflns_number_gt 1729 _reflns_number_observed 1729 _reflns_number_total 2028 _reflns_observed_criterion >2sigma(I) _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c0ob00735h.txt _[local]_cod_data_source_block MALIK1 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_geom_bond_publ_flag' value 'Y' changed to 'y' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (16 times). '_geom_angle_publ_flag' value 'Y' changed to 'y' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (24 times). Automatic conversion script Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius ; _cod_database_code 7151735 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.33011(12) 0.12171(9) 0.08954(10) 0.0303(2) Uani 1 d . . . C2 C 0.48729(17) 0.14018(13) 0.07666(14) 0.0282(3) Uani 1 d . . . C3 C 0.51201(17) 0.23260(14) -0.03347(14) 0.0294(3) Uani 1 d . . . H3A H 0.5375 0.1927 -0.1196 0.035 Uiso 1 calc R . . H3B H 0.5989 0.2894 -0.0044 0.035 Uiso 1 calc R . . C4 C 0.35188(17) 0.29818(14) -0.05082(13) 0.0283(3) Uani 1 d . . . H4 H 0.3264 0.3219 -0.1483 0.034 Uiso 1 calc R . . C5 C 0.33311(16) 0.40804(13) 0.04631(14) 0.0265(3) Uani 1 d . . . H5 H 0.3381 0.4863 -0.0044 0.032 Uiso 1 calc R . . C6 C 0.16905(16) 0.38896(13) 0.09830(13) 0.0268(3) Uani 1 d . . . C7 C 0.07813(18) 0.47115(15) 0.16815(15) 0.0338(3) Uani 1 d . . . H7 H 0.1149 0.5514 0.1855 0.041 Uiso 1 calc R . . C8 C -0.06794(18) 0.43273(16) 0.21188(16) 0.0383(4) Uani 1 d . . . H8 H -0.1304 0.4871 0.2605 0.046 Uiso 1 calc R . . C9 C -0.12297(18) 0.31523(17) 0.18480(17) 0.0400(4) Uani 1 d . . . H9 H -0.2221 0.2905 0.2158 0.048 Uiso 1 calc R . . C10 C -0.03395(18) 0.23367(16) 0.11266(16) 0.0365(4) Uani 1 d . . . H10 H -0.0727 0.1545 0.0922 0.044 Uiso 1 calc R . . C11 C 0.11379(16) 0.27140(14) 0.07116(14) 0.0282(3) Uani 1 d . . . C12 C 0.23307(17) 0.20199(14) -0.00551(14) 0.0297(3) Uani 1 d . . . H12 H 0.1814 0.1564 -0.0849 0.036 Uiso 1 calc R . . O13 O 0.58714(13) 0.08487(10) 0.14735(12) 0.0399(3) Uani 1 d . . . O14 O 0.45589(11) 0.40201(10) 0.15645(10) 0.0310(2) Uani 1 d . . . H14 H 0.4449 0.4597 0.2105 0.046 Uiso 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 0.0332(5) 0.0257(5) 0.0327(5) 0.0009(4) 0.0072(4) -0.0026(4) C2 0.0335(7) 0.0252(7) 0.0264(7) -0.0046(6) 0.0055(6) -0.0005(6) C3 0.0324(7) 0.0319(7) 0.0247(7) -0.0009(6) 0.0073(5) -0.0015(6) C4 0.0312(7) 0.0348(8) 0.0189(6) 0.0030(6) 0.0020(5) -0.0027(6) C5 0.0278(7) 0.0250(7) 0.0267(7) 0.0060(5) 0.0009(5) -0.0018(5) C6 0.0261(6) 0.0316(7) 0.0222(6) 0.0053(6) -0.0019(5) 0.0012(6) C7 0.0328(8) 0.0348(8) 0.0330(7) 0.0017(6) -0.0025(6) 0.0055(6) C8 0.0304(8) 0.0509(10) 0.0336(8) 0.0016(7) 0.0015(6) 0.0121(7) C9 0.0242(7) 0.0578(11) 0.0380(8) 0.0067(8) 0.0026(6) 0.0015(7) C10 0.0287(7) 0.0411(9) 0.0392(8) 0.0033(7) -0.0007(6) -0.0063(6) C11 0.0262(7) 0.0335(8) 0.0241(6) 0.0031(6) -0.0023(5) -0.0019(6) C12 0.0316(7) 0.0331(8) 0.0239(6) -0.0032(6) -0.0015(5) -0.0047(6) O13 0.0398(6) 0.0363(6) 0.0433(6) 0.0091(5) 0.0022(5) 0.0059(5) O14 0.0297(5) 0.0327(6) 0.0298(5) -0.0054(4) -0.0028(4) 0.0003(4) 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 C2 O1 C12 110.36(10) . . y O13 C2 O1 120.77(13) . . y O13 C2 C3 128.45(13) . . y O1 C2 C3 110.77(12) . . y C2 C3 C4 103.48(11) . . y C3 C4 C12 103.09(12) . . y C3 C4 C5 115.37(11) . . y C12 C4 C5 105.21(11) . . y O14 C5 C6 111.18(11) . . y O14 C5 C4 108.87(11) . . y C6 C5 C4 103.43(11) . . y C11 C6 C7 120.62(13) . . y C11 C6 C5 111.25(12) . . y C7 C6 C5 128.11(14) . . y C8 C7 C6 118.61(15) . . y C9 C8 C7 120.71(15) . . y C8 C9 C10 120.83(14) . . y C9 C10 C11 118.46(16) . . y C6 C11 C10 120.75(14) . . y C6 C11 C12 110.02(12) . . y C10 C11 C12 129.22(14) . . y O1 C12 C11 110.22(11) . . y O1 C12 C4 104.60(11) . . y C11 C12 C4 105.24(12) . . y 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 O1 C2 1.3407(17) . y O1 C12 1.4727(17) . y C2 O13 1.2029(17) . y C2 C3 1.497(2) . y C3 C4 1.514(2) . y C4 C12 1.531(2) . y C4 C5 1.542(2) . y C5 O14 1.4275(16) . y C5 C6 1.5066(19) . y C6 C11 1.384(2) . y C6 C7 1.385(2) . y C7 C8 1.384(2) . y C8 C9 1.383(3) . y C9 C10 1.383(2) . y C10 C11 1.3863(19) . y C11 C12 1.492(2) . y 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 O14 H14 O13 0.83 1.98 2.8029(15) 174.3 2_655