#------------------------------------------------------------------------------ #$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $ #$Revision: 202017 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/17/7151738.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_7151738 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_paper_doi 10.1039/c0ob00735h _journal_volume 9 _journal_year 2011 _chemical_formula_sum 'C17 H14 O6' _chemical_formula_weight 314.28 _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 94.935(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.6845(9) _cell_length_b 7.9964(10) _cell_length_c 26.937(3) _cell_measurement_reflns_used 29 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.010 _cell_measurement_theta_min 1.520 _cell_volume 1434.5(3) _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 293(2) _diffrn_detector_area_resol_mean 18.4 _diffrn_measured_fraction_theta_full 0.928 _diffrn_measured_fraction_theta_max 0.928 _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 0.1277 _diffrn_reflns_av_sigmaI/netI 0.0698 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 29442 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 1.52 _diffrn_standards_decay_% 0.000 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.6487 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS multiscan (Sheldrick, 1996)' _exptl_crystal_colour 'translucent colourless' _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rather regular thin needle' _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.303 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.095 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.185 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 2536 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.185 _refine_ls_R_factor_all 0.1350 _refine_ls_R_factor_gt 0.0793 _refine_ls_R_factor_obs 0.0793 _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^)+(0.0842P)^2^+0.1052P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1847 _refine_ls_wR_factor_gt 0.1549 _refine_ls_wR_factor_obs 0.1549 _refine_ls_wR_factor_ref 0.1847 _reflns_number_gt 1646 _reflns_number_observed 1646 _reflns_number_total 2536 _reflns_observed_criterion >2sigma(I) _reflns_threshold_expression >2sigma(I) _cod_data_source_file c0ob00735h.txt _cod_data_source_block MALIK4 _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 (26 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 (39 times). Automatic conversion script Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7151738 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 C1 C 0.5501(5) 0.3405(4) 0.17543(14) 0.0267(9) Uani 1 d . . . C2 C 0.6604(5) 0.2613(4) 0.21983(13) 0.0250(9) Uani 1 d . . . H2 H 0.7012 0.1475 0.2117 0.030 Uiso 1 calc R . . C3 C 0.8446(5) 0.3607(4) 0.24486(13) 0.0247(9) Uani 1 d . . . H3 H 0.9645 0.2897 0.2471 0.030 Uiso 1 calc R . . C4 C 0.7845(5) 0.3980(5) 0.29620(13) 0.0264(9) Uani 1 d . . . C5 C 0.8954(6) 0.4801(5) 0.33454(15) 0.0405(11) Uani 1 d . . . H5 H 1.0220 0.5222 0.3297 0.049 Uiso 1 calc R . . C6 C 0.8174(7) 0.4990(6) 0.37954(16) 0.0495(12) Uani 1 d . . . H6 H 0.8925 0.5523 0.4056 0.059 Uiso 1 calc R . . C7 C 0.6281(7) 0.4395(6) 0.38657(16) 0.0509(12) Uani 1 d . . . H7 H 0.5765 0.4545 0.4172 0.061 Uiso 1 calc R . . C8 C 0.5150(6) 0.3587(5) 0.34902(15) 0.0398(11) Uani 1 d . . . H8 H 0.3879 0.3179 0.3540 0.048 Uiso 1 calc R . . C9 C 0.5947(5) 0.3392(4) 0.30356(14) 0.0268(9) Uani 1 d . . . C10 C 0.5003(5) 0.2559(5) 0.25775(13) 0.0273(9) Uani 1 d . . . H10 H 0.4614 0.1406 0.2647 0.033 Uiso 1 calc R . . O11 O 0.3285(3) 0.3529(3) 0.23579(9) 0.0297(7) Uani 1 d . . . C12 C 0.3526(5) 0.3935(5) 0.18802(14) 0.0290(9) Uani 1 d . . . O13 O 0.8845(3) 0.5133(3) 0.22046(9) 0.0282(7) Uani 1 d . . . H13 H 0.9807 0.5007 0.2039 0.042 Uiso 1 calc R . . O14 O 0.2188(4) 0.4645(3) 0.16300(10) 0.0357(7) Uani 1 d . . . C15 C 0.6162(5) 0.3730(5) 0.13155(14) 0.0311(10) Uani 1 d . . . H15 H 0.5354 0.4300 0.1073 0.037 Uiso 1 calc R . . O16 O 0.8029(3) 0.3224(3) 0.12223(9) 0.0360(7) Uani 1 d . . . C17 C 0.8934(6) 0.4008(6) 0.08317(14) 0.0393(11) Uani 1 d . . . H17 H 1.0351 0.3680 0.0850 0.047 Uiso 1 calc R . . O18 O 0.7972(4) 0.3469(4) 0.03603(10) 0.0493(9) Uani 1 d . . . C19 C 0.7464(6) 0.4867(8) 0.00855(17) 0.0563(14) Uani 1 d . . . C20 C 0.7962(6) 0.6353(7) 0.03816(18) 0.0524(14) Uani 1 d . . . C21 C 0.8810(6) 0.5858(6) 0.08176(16) 0.0412(11) Uani 1 d . . . H21 H 0.9262 0.6566 0.1077 0.049 Uiso 1 calc R . . O22 O 0.6750(5) 0.4747(6) -0.03397(11) 0.0831(14) Uani 1 d . . . C23 C 0.7543(9) 0.8071(8) 0.0184(2) 0.091(2) Uani 1 d . . . H23A H 0.7809 0.8871 0.0448 0.136 Uiso 1 calc R . . H23B H 0.6161 0.8149 0.0056 0.136 Uiso 1 calc R . . H23C H 0.8390 0.8300 -0.0078 0.136 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 C1 0.025(2) 0.028(2) 0.027(2) -0.0013(18) 0.0019(17) -0.0022(16) C2 0.0192(18) 0.022(2) 0.034(2) -0.0024(18) 0.0048(16) 0.0026(15) C3 0.0221(19) 0.027(2) 0.025(2) 0.0048(17) 0.0020(16) 0.0013(15) C4 0.026(2) 0.028(2) 0.025(2) 0.0039(18) 0.0042(17) -0.0009(16) C5 0.040(2) 0.050(3) 0.031(2) 0.005(2) 0.000(2) -0.012(2) C6 0.058(3) 0.058(3) 0.032(3) -0.004(2) -0.001(2) -0.013(2) C7 0.072(3) 0.057(3) 0.025(2) 0.000(2) 0.012(2) -0.006(3) C8 0.040(2) 0.047(3) 0.033(3) 0.003(2) 0.010(2) -0.0031(19) C9 0.029(2) 0.025(2) 0.026(2) 0.0061(17) 0.0043(17) 0.0020(16) C10 0.0202(18) 0.029(2) 0.033(2) 0.0055(18) 0.0030(17) 0.0039(16) O11 0.0214(13) 0.0386(16) 0.0298(16) 0.0035(12) 0.0047(11) 0.0016(11) C12 0.026(2) 0.033(2) 0.028(2) -0.0050(19) 0.0035(18) -0.0072(18) O13 0.0266(14) 0.0303(15) 0.0289(15) 0.0042(12) 0.0089(11) -0.0026(11) O14 0.0238(14) 0.0499(18) 0.0325(16) 0.0047(14) -0.0023(12) 0.0047(13) C15 0.023(2) 0.041(3) 0.029(2) -0.0030(19) 0.0019(17) 0.0012(17) O16 0.0259(14) 0.0561(19) 0.0269(16) 0.0039(14) 0.0069(12) 0.0101(12) C17 0.029(2) 0.068(3) 0.021(2) -0.007(2) 0.0041(18) 0.004(2) O18 0.0383(17) 0.087(3) 0.0227(16) -0.0098(16) 0.0018(13) 0.0082(15) C19 0.030(2) 0.112(5) 0.028(3) 0.013(3) 0.011(2) 0.024(3) C20 0.037(3) 0.080(4) 0.044(3) 0.022(3) 0.021(2) 0.018(2) C21 0.032(2) 0.058(3) 0.035(3) 0.007(2) 0.0077(19) 0.003(2) O22 0.045(2) 0.182(4) 0.0216(19) 0.009(2) 0.0020(15) 0.030(2) C23 0.088(4) 0.110(5) 0.079(4) 0.057(4) 0.039(3) 0.039(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 C15 C1 C12 122.1(3) . . y C15 C1 C2 128.3(3) . . y C12 C1 C2 109.5(3) . . y C1 C2 C10 102.7(3) . . y C1 C2 C3 116.4(3) . . y C10 C2 C3 107.1(3) . . y O13 C3 C4 109.3(3) . . y O13 C3 C2 114.1(3) . . y C4 C3 C2 103.5(3) . . y C9 C4 C5 119.6(3) . . y C9 C4 C3 112.7(3) . . y C5 C4 C3 127.8(3) . . y C6 C5 C4 119.5(4) . . y C5 C6 C7 120.5(4) . . y C8 C7 C6 121.0(4) . . y C7 C8 C9 118.4(4) . . y C4 C9 C8 121.1(4) . . y C4 C9 C10 111.1(3) . . y C8 C9 C10 127.8(3) . . y O11 C10 C9 110.9(3) . . y O11 C10 C2 106.4(3) . . y C9 C10 C2 105.5(3) . . y C12 O11 C10 111.0(3) . . y O14 C12 O11 120.0(3) . . y O14 C12 C1 130.3(4) . . y O11 C12 C1 109.7(3) . . y C1 C15 O16 119.4(3) . . y C15 O16 C17 117.9(3) . . y O16 C17 O18 109.8(3) . . y O16 C17 C21 115.9(3) . . y O18 C17 C21 104.9(3) . . y C19 O18 C17 107.7(4) . . y O22 C19 O18 120.6(5) . . y O22 C19 C20 129.7(5) . . y O18 C19 C20 109.7(4) . . y C21 C20 C19 107.7(4) . . y C21 C20 C23 130.3(6) . . y C19 C20 C23 122.1(5) . . y C20 C21 C17 109.9(4) . . 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 C1 C15 1.323(5) . y C1 C12 1.454(5) . y C1 C2 1.491(5) . y C2 C10 1.542(5) . y C2 C3 1.568(5) . y C3 O13 1.422(4) . y C3 C4 1.503(5) . y C4 C9 1.383(5) . y C4 C5 1.384(5) . y C5 C6 1.369(6) . y C6 C7 1.380(6) . y C7 C8 1.372(6) . y C8 C9 1.385(5) . y C9 C10 1.494(5) . y C10 O11 1.467(4) . y O11 C12 1.350(4) . y C12 O14 1.213(4) . y C15 O16 1.356(4) . y O16 C17 1.406(5) . y C17 O18 1.439(4) . y C17 C21 1.482(6) . y O18 C19 1.367(6) . y C19 O22 1.206(5) . y C19 C20 1.454(7) . y C20 C21 1.320(6) . y C20 C23 1.490(7) . 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 O13 H13 O14 0.82 2.03 2.853(3) 178.9 1_655 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 26994270