#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/91/1519117.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_1519117 loop_ _publ_author_name 'Ward, Robert S.' 'Harman, Mary' 'Hursthouse, Michael B.' _publ_section_title ; C21H22O6 ; _journal_name_full 'Crystal Structure Report Archive' _journal_page_first 1022 _journal_year 1992 _chemical_formula_sum 'C21 H22 O6' _chemical_formula_weight 370.39 _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 geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 81.84(3) _cell_angle_beta 84.41(3) _cell_angle_gamma 78.71(1) _cell_formula_units_Z 2 _cell_length_a 8.270(5) _cell_length_b 8.870(4) _cell_length_c 13.050(9) _cell_measurement_temperature 293(2) _cell_volume 926.9(10) _computing_cell_refinement REFINE _computing_data_collection 'MADNES (Pflugrath & Messerschmidt, 1989)' _computing_data_reduction 'ABSURD (Karaulov, 1992)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.891 _diffrn_measured_fraction_theta_max 0.891 _diffrn_measurement_device_type 'Delft instruments FAST area detector' _diffrn_measurement_method 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'rotating anode generator' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.2479 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4396 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.67 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_crystal_colour unk _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_description unk _exptl_crystal_F_000 392 _refine_diff_density_max 0.171 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.054 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.446 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 307 _refine_ls_number_reflns 3801 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.446 _refine_ls_R_factor_all 0.0930 _refine_ls_R_factor_gt 0.0425 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0806 _refine_ls_wR_factor_ref 0.1216 _reflns_number_gt 1145 _reflns_number_total 3801 _reflns_threshold_expression >2\s(I) _cod_data_source_file eCrystal-1022.cif _cod_data_source_block s80 _cod_depositor_comments ; Citation : Ward, Robert S. and Harman, Mary and Hursthouse, Michael B. (1992) University of Southampton, Crystal Structure Report Archive. (doi:10.5258/ecrystals/1022) http://ecrystals.chem.soton.ac.uk/1022/ The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to the built-in table from CIF Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 3105 2015-03-04 15:46:00Z robertas ; _cod_original_sg_symbol_H-M P-1 _cod_database_code 1519117 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 O1 O 0.0696(3) 0.6730(3) 0.36517(18) 0.0619(6) Uani 1 1 d . . . H1 H 0.0615 0.7628 0.3374 0.093 Uiso 1 1 calc R . . O2 O -0.1086(3) 0.8255(2) 0.20975(18) 0.0612(6) Uani 1 1 d . . . O3 O -0.4528(3) 0.2493(3) -0.04282(15) 0.0577(6) Uani 1 1 d . . . O4 O -0.1863(3) 0.0407(3) 0.60982(18) 0.0689(7) Uani 1 1 d . . . O5 O -0.7222(3) 0.1986(3) 0.06317(17) 0.0668(7) Uani 1 1 d . . . O6 O -0.4600(3) 0.1179(2) 0.61944(15) 0.0556(6) Uani 1 1 d . . . C1 C -0.0370(3) 0.6013(3) 0.3240(2) 0.0412(6) Uani 1 1 d . . . C2 C -0.0538(3) 0.4531(3) 0.3668(2) 0.0396(6) Uani 1 1 d . . . C3 C -0.1651(3) 0.3751(3) 0.33098(19) 0.0363(6) Uani 1 1 d . . . C4 C -0.2607(3) 0.4509(3) 0.24910(19) 0.0358(6) Uani 1 1 d . . . C5 C -0.2405(4) 0.6015(3) 0.2052(2) 0.0403(6) Uani 1 1 d . . . C6 C -0.1318(4) 0.6765(3) 0.2430(2) 0.0421(6) Uani 1 1 d . . . C7 C -0.2406(6) 0.9291(4) 0.1621(3) 0.0580(9) Uani 1 1 d . . . C8 C -0.1836(4) 0.2179(3) 0.3890(2) 0.0409(6) Uani 1 1 d . . . C9 C -0.3208(4) 0.2371(3) 0.4764(2) 0.0388(6) Uani 1 1 d . . . C10 C -0.4955(4) 0.2391(3) 0.4491(2) 0.0405(6) Uani 1 1 d . . . C11 C -0.5703(4) 0.3786(3) 0.3744(2) 0.0416(6) Uani 1 1 d . . . C12 C -0.5289(3) 0.3500(3) 0.26194(19) 0.0375(6) Uani 1 1 d . . . C13 C -0.3850(3) 0.3798(3) 0.20590(19) 0.0367(6) Uani 1 1 d . . . C14 C -0.3067(4) 0.1201(3) 0.5727(2) 0.0468(7) Uani 1 1 d . . . C15 C -0.5830(4) 0.2208(4) 0.5566(2) 0.0510(7) Uani 1 1 d . . . C16 C -0.6435(4) 0.2882(3) 0.2159(2) 0.0429(6) Uani 1 1 d . . . C17 C -0.6152(4) 0.2569(3) 0.1138(2) 0.0467(7) Uani 1 1 d . . . C18 C -0.4702(4) 0.2868(3) 0.05610(19) 0.0414(6) Uani 1 1 d . . . C19 C -0.3588(4) 0.3489(3) 0.1010(2) 0.0403(6) Uani 1 1 d . . . C20 C -0.8753(5) 0.1785(7) 0.1176(3) 0.1090(19) Uani 1 1 d . . . H20A H -0.8550 0.1113 0.1813 0.164 Uiso 1 1 calc R . . H20B H -0.9373 0.1332 0.0757 0.164 Uiso 1 1 calc R . . H20C H -0.9371 0.2773 0.1327 0.164 Uiso 1 1 calc R . . C21 C -0.3072(5) 0.2739(5) -0.1045(2) 0.0722(11) Uani 1 1 d . . . H21A H -0.3005 0.3818 -0.1120 0.108 Uiso 1 1 calc R . . H21B H -0.3102 0.2428 -0.1717 0.108 Uiso 1 1 calc R . . H21C H -0.2123 0.2138 -0.0716 0.108 Uiso 1 1 calc R . . H2 H 0.012(4) 0.402(3) 0.427(2) 0.048(8) Uiso 1 1 d . . . H5 H -0.311(3) 0.656(3) 0.1493(19) 0.032(6) Uiso 1 1 d . . . H71 H -0.352(5) 0.937(4) 0.202(3) 0.086(13) Uiso 1 1 d . . . H72 H -0.256(5) 0.906(5) 0.096(3) 0.092(13) Uiso 1 1 d . . . H73 H -0.209(5) 1.033(5) 0.150(3) 0.085(12) Uiso 1 1 d . . . H81 H -0.081(4) 0.172(3) 0.418(2) 0.041(7) Uiso 1 1 d . . . H82 H -0.211(4) 0.148(3) 0.342(2) 0.045(8) Uiso 1 1 d . . . H9 H -0.316(4) 0.338(3) 0.5008(19) 0.041(7) Uiso 1 1 d . . . H10 H -0.493(4) 0.146(3) 0.413(2) 0.048(8) Uiso 1 1 d . . . H111 H -0.528(4) 0.476(3) 0.3855(19) 0.039(7) Uiso 1 1 d . . . H112 H -0.680(4) 0.394(3) 0.390(2) 0.049(8) Uiso 1 1 d . . . H151 H -0.617(4) 0.321(4) 0.589(2) 0.055(9) Uiso 1 1 d . . . H152 H -0.682(4) 0.175(4) 0.560(2) 0.057(9) Uiso 1 1 d . . . H16 H -0.741(4) 0.260(4) 0.257(2) 0.055(9) Uiso 1 1 d . . . H19 H -0.252(4) 0.376(3) 0.063(2) 0.047(8) 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 O1 0.0579(15) 0.0647(14) 0.0717(15) 0.0024(11) -0.0282(12) -0.0286(13) O2 0.0598(15) 0.0476(12) 0.0789(15) 0.0141(10) -0.0239(12) -0.0231(11) O3 0.0608(15) 0.0792(15) 0.0362(11) -0.0165(9) -0.0077(10) -0.0121(12) O4 0.0645(16) 0.0636(14) 0.0682(14) 0.0184(11) -0.0086(13) -0.0037(13) O5 0.0576(15) 0.0992(18) 0.0573(14) -0.0294(12) -0.0095(12) -0.0309(14) O6 0.0607(14) 0.0610(13) 0.0453(12) -0.0012(9) 0.0040(11) -0.0196(12) C1 0.0312(14) 0.0488(15) 0.0469(16) -0.0052(11) -0.0080(12) -0.0132(12) C2 0.0296(13) 0.0472(14) 0.0408(14) 0.0012(11) -0.0058(11) -0.0072(12) C3 0.0305(13) 0.0382(13) 0.0393(14) -0.0054(10) -0.0004(11) -0.0051(11) C4 0.0298(13) 0.0418(13) 0.0367(13) -0.0066(10) -0.0047(11) -0.0065(11) C5 0.0370(15) 0.0464(15) 0.0371(14) 0.0000(10) -0.0070(12) -0.0084(12) C6 0.0389(15) 0.0407(14) 0.0472(15) 0.0006(11) -0.0058(12) -0.0114(12) C7 0.076(3) 0.0435(16) 0.055(2) 0.0029(13) -0.0162(19) -0.0132(17) C8 0.0340(15) 0.0357(13) 0.0505(16) -0.0039(11) -0.0040(13) -0.0011(12) C9 0.0416(15) 0.0353(13) 0.0401(14) -0.0061(10) -0.0007(12) -0.0085(12) C10 0.0429(16) 0.0442(14) 0.0375(14) -0.0116(10) 0.0012(12) -0.0128(13) C11 0.0333(15) 0.0509(15) 0.0427(15) -0.0162(11) -0.0012(12) -0.0064(13) C12 0.0335(14) 0.0409(13) 0.0397(14) -0.0091(10) -0.0066(11) -0.0055(11) C13 0.0356(14) 0.0348(12) 0.0404(14) -0.0052(9) -0.0099(11) -0.0043(11) C14 0.0524(19) 0.0412(15) 0.0478(17) -0.0039(11) -0.0027(14) -0.0123(14) C15 0.0455(18) 0.0654(19) 0.0460(17) -0.0115(14) 0.0028(14) -0.0194(16) C16 0.0365(15) 0.0523(15) 0.0438(16) -0.0106(12) -0.0081(12) -0.0116(13) C17 0.0429(16) 0.0537(17) 0.0484(16) -0.0141(12) -0.0146(13) -0.0095(14) C18 0.0453(16) 0.0480(15) 0.0304(14) -0.0059(10) -0.0099(12) -0.0030(13) C19 0.0385(15) 0.0434(14) 0.0368(14) -0.0026(10) -0.0046(12) -0.0033(12) C20 0.068(3) 0.192(5) 0.098(3) -0.063(3) -0.002(2) -0.069(3) C21 0.068(2) 0.106(3) 0.0409(19) -0.0169(17) 0.0021(17) -0.010(2) 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 C1 O1 H1 109.5 . . C6 O2 C7 117.2(3) . . C18 O3 C21 117.8(2) . . C17 O5 C20 117.1(2) . . C14 O6 C15 109.8(2) . . O1 C1 C2 118.8(3) . . O1 C1 C6 121.5(3) . . C2 C1 C6 119.7(2) . . C1 C2 C3 121.8(3) . . C1 C2 H2 119.0(16) . . C3 C2 H2 119.2(16) . . C2 C3 C4 118.5(2) . . C2 C3 C8 117.4(2) . . C4 C3 C8 124.0(2) . . C3 C4 C5 119.1(2) . . C3 C4 C13 123.0(2) . . C5 C4 C13 117.9(2) . . C6 C5 C4 121.2(3) . . C6 C5 H5 119.9(14) . . C4 C5 H5 118.8(15) . . O2 C6 C5 126.0(3) . . O2 C6 C1 114.2(2) . . C5 C6 C1 119.7(2) . . O2 C7 H71 116(2) . . O2 C7 H72 113(3) . . H71 C7 H72 106(3) . . O2 C7 H73 107(2) . . H71 C7 H73 109(3) . . H72 C7 H73 106(3) . . C3 C8 C9 110.1(2) . . C3 C8 H81 107.9(16) . . C9 C8 H81 109.8(16) . . C3 C8 H82 111.9(15) . . C9 C8 H82 108.5(17) . . H81 C8 H82 109(2) . . C14 C9 C10 101.7(2) . . C14 C9 C8 118.2(2) . . C10 C9 C8 117.1(2) . . C14 C9 H9 104.9(15) . . C10 C9 H9 109.3(17) . . C8 C9 H9 104.8(16) . . C15 C10 C9 100.7(2) . . C15 C10 C11 116.2(2) . . C9 C10 C11 115.6(2) . . C15 C10 H10 110.9(16) . . C9 C10 H10 107.5(18) . . C11 C10 H10 105.8(16) . . C12 C11 C10 111.5(2) . . C12 C11 H111 108.7(14) . . C10 C11 H111 110.6(15) . . C12 C11 H112 110.7(18) . . C10 C11 H112 106.6(19) . . H111 C11 H112 109(2) . . C13 C12 C16 120.2(2) . . C13 C12 C11 123.1(2) . . C16 C12 C11 116.7(3) . . C12 C13 C19 118.4(2) . . C12 C13 C4 122.9(2) . . C19 C13 C4 118.6(2) . . O4 C14 O6 121.3(3) . . O4 C14 C9 130.1(3) . . O6 C14 C9 108.6(3) . . O6 C15 C10 104.1(2) . . O6 C15 H151 107.6(17) . . C10 C15 H151 114.6(17) . . O6 C15 H152 109.3(19) . . C10 C15 H152 114.6(18) . . H151 C15 H152 106(3) . . C17 C16 C12 120.7(3) . . C17 C16 H16 118.8(18) . . C12 C16 H16 120.4(18) . . O5 C17 C16 124.1(3) . . O5 C17 C18 116.3(2) . . C16 C17 C18 119.7(3) . . O3 C18 C19 125.4(3) . . O3 C18 C17 115.1(3) . . C19 C18 C17 119.6(2) . . C18 C19 C13 121.4(3) . . C18 C19 H19 123.8(16) . . C13 C19 H19 114.8(16) . . O5 C20 H20A 109.5 . . O5 C20 H20B 109.5 . . H20A C20 H20B 109.5 . . O5 C20 H20C 109.5 . . H20A C20 H20C 109.5 . . H20B C20 H20C 109.5 . . O3 C21 H21A 109.5 . . O3 C21 H21B 109.5 . . H21A C21 H21B 109.5 . . O3 C21 H21C 109.5 . . H21A C21 H21C 109.5 . . H21B C21 H21C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C1 1.370(3) . O1 H1 0.8200 . O2 C6 1.375(3) . O2 C7 1.414(4) . O3 C18 1.366(3) . O3 C21 1.417(4) . O4 C14 1.202(4) . O5 C17 1.370(3) . O5 C20 1.421(4) . O6 C14 1.355(4) . O6 C15 1.459(4) . C1 C2 1.382(4) . C1 C6 1.391(4) . C2 C3 1.404(4) . C2 H2 1.00(3) . C3 C4 1.405(3) . C3 C8 1.517(4) . C4 C5 1.412(4) . C4 C13 1.497(4) . C5 C6 1.381(4) . C5 H5 0.99(3) . C7 H71 1.01(4) . C7 H72 0.94(4) . C7 H73 0.99(4) . C8 C9 1.531(4) . C8 H81 0.95(3) . C8 H82 1.00(3) . C9 C14 1.511(4) . C9 C10 1.518(4) . C9 H9 1.00(3) . C10 C15 1.517(4) . C10 C11 1.530(4) . C10 H10 1.00(3) . C11 C12 1.519(4) . C11 H111 1.03(3) . C11 H112 0.90(3) . C12 C13 1.386(4) . C12 C16 1.402(4) . C13 C19 1.422(4) . C15 H151 1.02(3) . C15 H152 0.98(3) . C16 C17 1.389(4) . C16 H16 0.98(3) . C17 C18 1.402(4) . C18 C19 1.375(4) . C19 H19 1.03(3) . C20 H20A 0.9600 . C20 H20B 0.9600 . C20 H20C 0.9600 . C21 H21A 0.9600 . C21 H21B 0.9600 . C21 H21C 0.9600 .