#------------------------------------------------------------------------------ #$Date: 2016-03-22 11:46:30 +0200 (Tue, 22 Mar 2016) $ #$Revision: 178915 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/11/44/4114411.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_4114411 loop_ _publ_author_name 'Wei He' 'Xiufeng Sun' 'Alison J. Frontier' _publ_section_title ; Polarizing the Nazarov Cyclization: Efficient Catalysis under Mild Conditions ; _journal_name_full 'Journal of the American Chemical Society' _journal_page_first 14278 _journal_page_last 14279 _journal_paper_doi 10.1021/ja037910b _journal_volume 125 _journal_year 2003 _chemical_formula_moiety 'C21 H26 O6' _chemical_formula_sum 'C21 H26 O6' _chemical_formula_weight 374.42 _chemical_name_common frowh01 _chemical_name_systematic ; 12a ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 74.5680(10) _cell_angle_beta 85.4520(10) _cell_angle_gamma 74.7850(10) _cell_formula_units_Z 2 _cell_length_a 7.2589(4) _cell_length_b 10.2403(5) _cell_length_c 13.9655(7) _cell_measurement_reflns_used 6529 _cell_measurement_temperature 193(2) _cell_measurement_theta_max 28 _cell_measurement_theta_min 2 _cell_volume 965.55(9) _computing_cell_refinement SAINT _computing_data_collection SMART _computing_data_reduction XPREP _computing_molecular_graphics ORTEP _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution SIR-92 _diffrn_ambient_temperature 193(2) _diffrn_measured_fraction_theta_full 0.962 _diffrn_measured_fraction_theta_max 0.962 _diffrn_measurement_device_type SMART _diffrn_measurement_method multirun _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 0.0132 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 11766 _diffrn_reflns_theta_full 28.31 _diffrn_reflns_theta_max 28.31 _diffrn_reflns_theta_min 2.13 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details SADABS _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.288 _exptl_crystal_description block _exptl_crystal_F_000 400 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.36 _refine_diff_density_max 0.245 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.033 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 348 _refine_ls_number_reflns 4634 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0407 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.1980P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1030 _refine_ls_wR_factor_ref 0.1085 _reflns_number_gt 3931 _reflns_number_total 4634 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ja037910bsi20030814_043516_1.cif _cod_data_source_block frowh01 _cod_database_code 4114411 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 C1 C 0.73016(16) 0.28940(11) 0.27017(8) 0.0287(2) Uani 1 1 d C2 C 0.71227(17) 0.42511(11) 0.18731(9) 0.0330(3) Uani 1 1 d C3 C 0.78247(17) 0.38544(12) 0.09459(9) 0.0345(3) Uani 1 1 d C4 C 0.7501(2) 0.47099(16) 0.00384(11) 0.0455(3) Uani 1 1 d C5 C 0.7963(3) 0.4218(2) -0.08821(11) 0.0593(4) Uani 1 1 d C6 C 0.8906(3) 0.2652(2) -0.07025(12) 0.0618(4) Uani 1 1 d C7 C 0.8233(3) 0.17952(17) 0.02738(11) 0.0503(4) Uani 1 1 d C8 C 0.86457(18) 0.22894(12) 0.11594(9) 0.0354(3) Uani 1 1 d C9 C 0.74877(16) 0.17734(11) 0.21215(8) 0.0276(2) Uani 1 1 d C10 C 1.0796(2) 0.19102(17) 0.13600(13) 0.0501(4) Uani 1 1 d C11 C 0.55996(17) 0.30184(11) 0.33915(9) 0.0316(2) Uani 1 1 d C12 C 0.4462(2) 0.3372(2) 0.49551(12) 0.0513(4) Uani 1 1 d C13 C 0.82014(16) 0.02424(11) 0.26688(8) 0.0285(2) Uani 1 1 d C14 C 0.96938(17) -0.02911(12) 0.33600(8) 0.0313(2) Uani 1 1 d C15 C 1.03770(18) -0.17183(12) 0.37803(9) 0.0334(3) Uani 1 1 d C16 C 0.95819(17) -0.26528(11) 0.35042(8) 0.0301(2) Uani 1 1 d C17 C 0.80841(16) -0.21929(11) 0.28417(8) 0.0289(2) Uani 1 1 d C18 C 0.74152(16) -0.07496(11) 0.24371(8) 0.0287(2) Uani 1 1 d C19 C 1.2221(2) 0.01933(15) 0.41095(12) 0.0461(3) Uani 1 1 d C20 C 0.9701(2) -0.50571(12) 0.36528(10) 0.0360(3) Uani 1 1 d C21 C 0.5136(2) -0.11587(14) 0.14682(12) 0.0441(3) Uani 1 1 d O1 O 0.64670(15) 0.54264(9) 0.19806(7) 0.0467(2) Uani 1 1 d O2 O 0.40364(13) 0.29812(11) 0.31946(8) 0.0495(3) Uani 1 1 d O3 O 0.60300(12) 0.32001(10) 0.42538(6) 0.0392(2) Uani 1 1 d O4 O 1.04379(13) 0.06746(8) 0.36067(7) 0.0400(2) Uani 1 1 d O5 O 1.03834(13) -0.40332(8) 0.39422(7) 0.0402(2) Uani 1 1 d O6 O 0.59494(12) -0.02146(8) 0.17679(7) 0.0383(2) Uani 1 1 d H1 H 0.843(2) 0.2760(14) 0.3072(10) 0.035(3) Uiso 1 1 d H4 H 0.690(2) 0.5677(18) -0.0040(12) 0.052(4) Uiso 1 1 d H5A H 0.681(3) 0.441(2) -0.1238(15) 0.074(6) Uiso 1 1 d H6A H 1.032(3) 0.2507(19) -0.0701(13) 0.065(5) Uiso 1 1 d H6B H 0.864(3) 0.233(2) -0.1281(15) 0.072(6) Uiso 1 1 d H7A H 0.882(3) 0.079(2) 0.0376(13) 0.062(5) Uiso 1 1 d H7B H 0.680(2) 0.1919(16) 0.0246(11) 0.047(4) Uiso 1 1 d H9 H 0.6198(18) 0.1890(13) 0.1889(9) 0.026(3) Uiso 1 1 d H10A H 1.151(2) 0.2268(18) 0.0744(13) 0.061(5) Uiso 1 1 d H10B H 1.128(3) 0.090(2) 0.1580(13) 0.063(5) Uiso 1 1 d H10C H 1.112(2) 0.2304(18) 0.1886(13) 0.059(5) Uiso 1 1 d H12A H 0.351(3) 0.4217(19) 0.4674(12) 0.057(5) Uiso 1 1 d H12B H 0.392(3) 0.256(2) 0.5112(13) 0.063(5) Uiso 1 1 d H12C H 0.503(3) 0.3450(18) 0.5542(14) 0.061(5) Uiso 1 1 d H15 H 1.139(2) -0.2057(15) 0.4263(11) 0.041(4) Uiso 1 1 d H17 H 0.7555(18) -0.2814(14) 0.2651(10) 0.030(3) Uiso 1 1 d H19A H 1.255(2) 0.1017(19) 0.4157(13) 0.060(5) Uiso 1 1 d H19B H 1.210(2) -0.0383(19) 0.4779(13) 0.055(4) Uiso 1 1 d H19C H 1.322(3) -0.0324(19) 0.3724(13) 0.063(5) Uiso 1 1 d H20A H 0.835(2) -0.4969(16) 0.3795(11) 0.044(4) Uiso 1 1 d H20B H 0.992(2) -0.4994(15) 0.2938(12) 0.045(4) Uiso 1 1 d H20C H 1.044(2) -0.5966(18) 0.4044(12) 0.054(4) Uiso 1 1 d H21A H 0.450(3) -0.1684(19) 0.2016(13) 0.061(5) Uiso 1 1 d H21B H 0.609(2) -0.1813(17) 0.1169(11) 0.049(4) Uiso 1 1 d H21C H 0.417(2) -0.0543(17) 0.0970(12) 0.053(4) Uiso 1 1 d H5B H 0.873(3) 0.477(2) -0.1339(16) 0.083(6) 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 0.0315(5) 0.0210(5) 0.0339(6) -0.0066(4) -0.0008(4) -0.0074(4) C2 0.0343(6) 0.0229(5) 0.0415(6) -0.0039(4) -0.0064(5) -0.0096(4) C3 0.0320(6) 0.0307(6) 0.0381(6) -0.0009(5) -0.0008(5) -0.0111(5) C4 0.0428(7) 0.0418(7) 0.0447(7) 0.0052(6) -0.0035(6) -0.0138(6) C5 0.0584(10) 0.0750(11) 0.0351(7) 0.0052(7) -0.0019(7) -0.0197(8) C6 0.0642(11) 0.0802(12) 0.0362(8) -0.0138(8) 0.0118(7) -0.0148(9) C7 0.0653(10) 0.0476(8) 0.0370(7) -0.0158(6) 0.0102(6) -0.0103(7) C8 0.0373(6) 0.0304(6) 0.0340(6) -0.0051(5) 0.0044(5) -0.0052(5) C9 0.0311(5) 0.0207(5) 0.0301(5) -0.0066(4) 0.0002(4) -0.0051(4) C10 0.0345(7) 0.0477(8) 0.0537(9) 0.0016(7) 0.0083(6) -0.0030(6) C11 0.0350(6) 0.0226(5) 0.0381(6) -0.0098(4) 0.0005(5) -0.0070(4) C12 0.0447(8) 0.0663(10) 0.0420(8) -0.0217(7) 0.0071(6) -0.0065(8) C13 0.0327(5) 0.0214(5) 0.0305(5) -0.0064(4) 0.0000(4) -0.0055(4) C14 0.0371(6) 0.0255(5) 0.0332(6) -0.0071(4) -0.0021(5) -0.0110(5) C15 0.0381(6) 0.0271(5) 0.0336(6) -0.0036(4) -0.0079(5) -0.0081(5) C16 0.0370(6) 0.0216(5) 0.0295(5) -0.0041(4) -0.0011(4) -0.0058(4) C17 0.0346(6) 0.0224(5) 0.0315(6) -0.0090(4) -0.0002(4) -0.0081(4) C18 0.0306(5) 0.0247(5) 0.0297(5) -0.0077(4) -0.0016(4) -0.0041(4) C19 0.0490(8) 0.0357(7) 0.0562(9) -0.0059(6) -0.0184(7) -0.0160(6) C20 0.0447(7) 0.0232(5) 0.0398(7) -0.0077(5) -0.0062(5) -0.0067(5) C21 0.0438(7) 0.0319(6) 0.0594(9) -0.0167(6) -0.0185(7) -0.0038(6) O1 0.0617(6) 0.0212(4) 0.0569(6) -0.0083(4) -0.0134(5) -0.0082(4) O2 0.0371(5) 0.0657(7) 0.0580(6) -0.0326(5) 0.0066(4) -0.0190(5) O3 0.0368(5) 0.0459(5) 0.0348(5) -0.0138(4) 0.0010(4) -0.0070(4) O4 0.0459(5) 0.0256(4) 0.0505(5) -0.0060(4) -0.0164(4) -0.0114(4) O5 0.0530(5) 0.0211(4) 0.0446(5) -0.0018(3) -0.0175(4) -0.0078(4) O6 0.0417(5) 0.0243(4) 0.0490(5) -0.0093(4) -0.0170(4) -0.0039(3) 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 C11 C1 C2 110.56(9) C11 C1 C9 114.08(9) C2 C1 C9 103.06(9) O1 C2 C3 127.46(11) O1 C2 C1 125.01(12) C3 C2 C1 107.50(9) C4 C3 C2 124.64(12) C4 C3 C8 124.50(13) C2 C3 C8 110.01(10) C3 C4 C5 122.98(14) C4 C5 C6 114.30(13) C5 C6 C7 112.22(13) C8 C7 C6 110.98(14) C3 C8 C7 108.44(11) C3 C8 C10 110.65(11) C7 C8 C10 111.54(12) C3 C8 C9 100.83(9) C7 C8 C9 113.16(11) C10 C8 C9 111.70(10) C13 C9 C1 118.43(9) C13 C9 C8 115.56(9) C1 C9 C8 104.06(9) O2 C11 O3 123.72(11) O2 C11 C1 124.65(11) O3 C11 C1 111.62(10) C18 C13 C14 116.08(10) C18 C13 C9 118.78(10) C14 C13 C9 125.03(10) O4 C14 C15 121.42(10) O4 C14 C13 116.36(10) C15 C14 C13 122.22(10) C16 C15 C14 119.23(11) O5 C16 C17 123.96(10) O5 C16 C15 114.69(10) C17 C16 C15 121.35(10) C16 C17 C18 118.13(10) O6 C18 C17 121.53(10) O6 C18 C13 115.50(9) C17 C18 C13 122.96(10) C11 O3 C12 115.55(11) C14 O4 C19 118.20(9) C16 O5 C20 117.70(9) C18 O6 C21 118.63(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C11 1.5049(16) C1 C2 1.5363(15) C1 C9 1.5451(15) C2 O1 1.2173(14) C2 C3 1.4724(18) C3 C4 1.3332(18) C3 C8 1.5116(17) C4 C5 1.485(2) C5 C6 1.529(3) C6 C7 1.533(2) C7 C8 1.5319(19) C8 C10 1.5359(19) C8 C9 1.5708(16) C9 C13 1.5197(14) C11 O2 1.2010(15) C11 O3 1.3386(14) C12 O3 1.4477(16) C13 C18 1.4038(15) C13 C14 1.4066(16) C14 O4 1.3710(13) C14 C15 1.3913(15) C15 C16 1.3853(16) C16 O5 1.3695(13) C16 C17 1.3852(16) C17 C18 1.4007(15) C18 O6 1.3730(13) C19 O4 1.4268(16) C20 O5 1.4278(14) C21 O6 1.4185(15) 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 C11 C1 C2 O1 37.71(16) C9 C1 C2 O1 160.01(11) C11 C1 C2 C3 -140.57(10) C9 C1 C2 C3 -18.26(12) O1 C2 C3 C4 -14.2(2) C1 C2 C3 C4 164.04(12) O1 C2 C3 C8 175.97(12) C1 C2 C3 C8 -5.81(13) C2 C3 C4 C5 -169.98(13) C8 C3 C4 C5 -1.6(2) C3 C4 C5 C6 -2.0(2) C4 C5 C6 C7 31.5(2) C5 C6 C7 C8 -58.1(2) C4 C3 C8 C7 -24.04(17) C2 C3 C8 C7 145.83(11) C4 C3 C8 C10 98.59(15) C2 C3 C8 C10 -91.55(13) C4 C3 C8 C9 -143.10(12) C2 C3 C8 C9 26.76(12) C6 C7 C8 C3 52.32(16) C6 C7 C8 C10 -69.76(16) C6 C7 C8 C9 163.30(12) C11 C1 C9 C13 -75.65(13) C2 C1 C9 C13 164.45(9) C11 C1 C9 C8 154.46(9) C2 C1 C9 C8 34.56(11) C3 C8 C9 C13 -169.00(10) C7 C8 C9 C13 75.40(13) C10 C8 C9 C13 -51.46(14) C3 C8 C9 C1 -37.41(11) C7 C8 C9 C1 -153.01(11) C10 C8 C9 C1 80.13(12) C2 C1 C11 O2 74.26(15) C9 C1 C11 O2 -41.33(16) C2 C1 C11 O3 -104.72(11) C9 C1 C11 O3 139.68(10) C1 C9 C13 C18 143.30(11) C8 C9 C13 C18 -92.29(13) C1 C9 C13 C14 -40.81(16) C8 C9 C13 C14 83.60(14) C18 C13 C14 O4 -178.55(10) C9 C13 C14 O4 5.46(17) C18 C13 C14 C15 0.96(17) C9 C13 C14 C15 -175.03(11) O4 C14 C15 C16 -179.79(11) C13 C14 C15 C16 0.73(18) C14 C15 C16 O5 178.55(10) C14 C15 C16 C17 -1.97(18) O5 C16 C17 C18 -179.15(10) C15 C16 C17 C18 1.42(18) C16 C17 C18 O6 179.31(10) C16 C17 C18 C13 0.39(17) C14 C13 C18 O6 179.48(10) C9 C13 C18 O6 -4.26(15) C14 C13 C18 C17 -1.53(17) C9 C13 C18 C17 174.73(10) O2 C11 O3 C12 -0.75(18) C1 C11 O3 C12 178.25(11) C15 C14 O4 C19 15.18(18) C13 C14 O4 C19 -165.31(12) C17 C16 O5 C20 3.70(17) C15 C16 O5 C20 -176.83(11) C17 C18 O6 C21 -1.48(17) C13 C18 O6 C21 177.52(11)