#------------------------------------------------------------------------------ #$Date: 2016-03-22 11:46:30 +0200 (Tue, 22 Mar 2016) $ #$Revision: 178915 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/11/44/4114412.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_4114412 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_sum 'C19 H22 O7' _chemical_formula_weight 362.37 _chemical_name_common frowh02 _chemical_name_systematic ; 4a ; _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_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 109.88(1) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.1639(19) _cell_length_b 12.296(2) _cell_length_c 14.944(3) _cell_measurement_reflns_used 6471 _cell_measurement_temperature 193(2) _cell_measurement_theta_max 28 _cell_measurement_theta_min 2 _cell_volume 1756.3(6) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 193(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 13812 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.13 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.370 _exptl_crystal_description block _exptl_crystal_F_000 768 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.207 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 323 _refine_ls_number_reflns 3582 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0400 _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^)+(0.0519P)^2^+0.5186P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0974 _refine_ls_wR_factor_ref 0.1032 _reflns_number_gt 2922 _reflns_number_total 3582 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ja037910bsi20030814_043516_2.cif _cod_data_source_block frowh02 _cod_original_cell_volume 1756.4(6) _cod_database_code 4114412 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_symmetry_multiplicity _atom_site_calc_flag C1 C 0.73031(14) 0.23672(12) 0.57392(10) 0.0256(3) Uani 1 1 d C2 C 0.88981(15) 0.23457(12) 0.61534(11) 0.0287(3) Uani 1 1 d C3 C 0.92528(14) 0.20483(12) 0.71530(10) 0.0274(3) Uani 1 1 d C5 C 1.07635(17) 0.15942(15) 0.86847(12) 0.0387(4) Uani 1 1 d C6 C 0.95634(18) 0.09480(14) 0.87898(12) 0.0380(4) Uani 1 1 d C7 C 0.81993(16) 0.15723(14) 0.83657(11) 0.0313(3) Uani 1 1 d C8 C 0.81198(14) 0.19714(11) 0.74093(10) 0.0255(3) Uani 1 1 d C9 C 0.67987(14) 0.22871(11) 0.66147(10) 0.0243(3) Uani 1 1 d C11 C 0.67104(15) 0.33509(12) 0.51451(10) 0.0275(3) Uani 1 1 d C12 C 0.4750(2) 0.39931(17) 0.38747(14) 0.0443(4) Uani 1 1 d C13 C 0.55639(14) 0.15358(11) 0.64803(9) 0.0239(3) Uani 1 1 d C14 C 0.42607(14) 0.19340(11) 0.64467(10) 0.0259(3) Uani 1 1 d C15 C 0.31216(15) 0.12493(12) 0.63440(11) 0.0288(3) Uani 1 1 d C16 C 0.33073(15) 0.01411(12) 0.62742(11) 0.0305(3) Uani 1 1 d C17 C 0.45744(15) -0.02925(12) 0.62849(11) 0.0296(3) Uani 1 1 d C18 C 0.56776(14) 0.04077(12) 0.63825(10) 0.0261(3) Uani 1 1 d C19 C 0.28423(18) 0.35123(15) 0.63347(16) 0.0431(4) Uani 1 1 d C20 C 0.1053(3) -0.0269(2) 0.6339(3) 0.0789(9) Uani 1 1 d C21 C 0.7093(2) -0.10350(14) 0.61384(15) 0.0410(4) Uani 1 1 d O1 O 0.96919(11) 0.24880(10) 0.57130(8) 0.0432(3) Uani 1 1 d O2 O 0.71990(12) 0.42492(9) 0.52832(9) 0.0426(3) Uani 1 1 d O3 O 0.55143(11) 0.31040(9) 0.44515(7) 0.0357(3) Uani 1 1 d O4 O 1.06042(10) 0.18363(9) 0.76988(8) 0.0352(3) Uani 1 1 d O5 O 0.41785(10) 0.30370(8) 0.65289(9) 0.0396(3) Uani 1 1 d O6 O 0.22777(12) -0.06155(9) 0.61744(10) 0.0479(3) Uani 1 1 d O7 O 0.69657(10) 0.00615(8) 0.64029(8) 0.0336(3) Uani 1 1 d H1 H 0.7025(15) 0.1722(13) 0.5372(11) 0.022(4) Uiso 1 1 d H5A H 1.1633(19) 0.1179(15) 0.8910(13) 0.041(5) Uiso 1 1 d H5B H 1.0848(19) 0.2314(16) 0.9049(13) 0.048(5) Uiso 1 1 d H6A H 0.9766(18) 0.0811(14) 0.9485(13) 0.040(5) Uiso 1 1 d H6B H 0.9527(18) 0.0233(16) 0.8455(12) 0.041(5) Uiso 1 1 d H7A H 0.7373(18) 0.1093(14) 0.8290(11) 0.034(4) Uiso 1 1 d H7B H 0.8141(17) 0.2154(15) 0.8758(12) 0.036(5) Uiso 1 1 d H9 H 0.6504(16) 0.3007(13) 0.6757(11) 0.026(4) Uiso 1 1 d H12A H 0.444(3) 0.448(2) 0.4219(18) 0.079(8) Uiso 1 1 d H12B H 0.522(3) 0.4297(19) 0.3488(18) 0.077(7) Uiso 1 1 d H12C H 0.385(3) 0.366(2) 0.3418(18) 0.082(8) Uiso 1 1 d H15 H 0.2259(18) 0.1527(14) 0.6329(11) 0.034(4) Uiso 1 1 d H17 H 0.4657(17) -0.1058(15) 0.6237(12) 0.036(4) Uiso 1 1 d H19A H 0.296(2) 0.425(2) 0.6381(17) 0.077(7) Uiso 1 1 d H19B H 0.239(2) 0.3223(18) 0.6823(16) 0.070(7) Uiso 1 1 d H19C H 0.220(3) 0.3295(19) 0.5730(18) 0.077(7) Uiso 1 1 d H20A H 0.057(2) 0.023(2) 0.5881(16) 0.063(7) Uiso 1 1 d H20B H 0.048(3) -0.091(2) 0.6256(19) 0.093(8) Uiso 1 1 d H21A H 0.804(2) -0.1107(17) 0.6136(15) 0.060(6) Uiso 1 1 d H21B H 0.701(2) -0.1529(18) 0.6620(15) 0.053(6) Uiso 1 1 d H21C H 0.641(2) -0.1213(17) 0.5521(15) 0.055(6) Uiso 1 1 d H20C H 0.121(3) 0.013(3) 0.692(2) 0.115(12) 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 0.0239(7) 0.0236(7) 0.0302(7) -0.0017(6) 0.0103(6) -0.0014(5) C2 0.0243(7) 0.0273(8) 0.0366(8) 0.0016(6) 0.0131(6) 0.0004(6) C3 0.0218(7) 0.0262(7) 0.0332(8) 0.0006(6) 0.0081(6) -0.0013(5) C5 0.0296(8) 0.0433(10) 0.0375(9) 0.0081(8) 0.0040(7) 0.0015(7) C6 0.0396(9) 0.0366(9) 0.0365(9) 0.0066(7) 0.0111(7) -0.0004(7) C7 0.0303(8) 0.0339(8) 0.0303(8) -0.0003(7) 0.0111(6) -0.0051(6) C8 0.0240(7) 0.0222(7) 0.0297(7) -0.0035(5) 0.0082(6) -0.0041(5) C9 0.0227(7) 0.0208(7) 0.0310(7) -0.0017(5) 0.0113(6) -0.0012(5) C11 0.0262(7) 0.0296(8) 0.0294(7) -0.0010(6) 0.0130(6) 0.0017(6) C12 0.0374(10) 0.0559(12) 0.0362(10) 0.0084(9) 0.0082(8) 0.0174(8) C13 0.0212(7) 0.0247(7) 0.0263(7) -0.0017(5) 0.0087(5) -0.0017(5) C14 0.0251(7) 0.0235(7) 0.0292(7) -0.0031(5) 0.0095(6) -0.0010(5) C15 0.0211(7) 0.0300(8) 0.0367(8) -0.0050(6) 0.0118(6) -0.0021(6) C16 0.0258(7) 0.0282(8) 0.0385(8) -0.0042(6) 0.0124(6) -0.0078(6) C17 0.0311(8) 0.0210(7) 0.0367(8) -0.0040(6) 0.0115(6) -0.0020(6) C18 0.0225(7) 0.0272(7) 0.0281(7) -0.0022(6) 0.0079(6) 0.0013(5) C19 0.0314(9) 0.0290(9) 0.0665(13) -0.0022(8) 0.0136(9) 0.0060(7) C20 0.0427(12) 0.0411(13) 0.170(3) -0.0075(17) 0.0579(17) -0.0130(10) C21 0.0362(10) 0.0291(9) 0.0592(12) -0.0083(8) 0.0182(9) 0.0060(7) O1 0.0292(6) 0.0620(8) 0.0439(7) 0.0133(6) 0.0197(5) 0.0038(5) O2 0.0440(7) 0.0288(6) 0.0504(7) 0.0036(5) 0.0103(5) -0.0018(5) O3 0.0280(6) 0.0403(6) 0.0344(6) 0.0029(5) 0.0050(5) 0.0042(5) O4 0.0209(5) 0.0453(7) 0.0371(6) 0.0073(5) 0.0070(4) 0.0007(4) O5 0.0232(5) 0.0233(6) 0.0722(8) -0.0081(5) 0.0159(5) 0.0008(4) O6 0.0313(6) 0.0310(6) 0.0873(10) -0.0110(6) 0.0280(6) -0.0108(5) O7 0.0243(5) 0.0256(5) 0.0523(7) -0.0065(5) 0.0147(5) 0.0023(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 C11 C1 C2 114.29(12) C11 C1 C9 111.49(11) C2 C1 C9 105.37(11) O1 C2 C3 127.76(14) O1 C2 C1 125.96(14) C3 C2 C1 106.15(12) C8 C3 O4 127.37(13) C8 C3 C2 112.00(13) O4 C3 C2 120.55(12) O4 C5 C6 113.41(13) C5 C6 C7 110.21(14) C8 C7 C6 108.11(13) C3 C8 C7 121.93(13) C3 C8 C9 112.30(13) C7 C8 C9 125.72(12) C8 C9 C13 114.98(11) C8 C9 C1 102.56(11) C13 C9 C1 114.84(11) O2 C11 O3 123.81(14) O2 C11 C1 125.53(13) O3 C11 C1 110.60(12) C14 C13 C18 116.95(12) C14 C13 C9 121.56(12) C18 C13 C9 121.49(12) O5 C14 C13 115.52(12) O5 C14 C15 122.28(13) C13 C14 C15 122.20(13) C16 C15 C14 118.19(13) O6 C16 C15 123.92(13) O6 C16 C17 114.30(13) C15 C16 C17 121.78(13) C18 C17 C16 118.55(13) O7 C18 C17 123.02(13) O7 C18 C13 114.68(12) C17 C18 C13 122.30(13) C11 O3 C12 116.97(13) C3 O4 C5 112.76(11) C14 O5 C19 118.37(12) C16 O6 C20 117.47(14) C18 O7 C21 117.77(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C11 1.500(2) C1 C2 1.526(2) C1 C9 1.5623(19) C2 O1 1.2148(18) C2 C3 1.459(2) C3 C8 1.335(2) C3 O4 1.3630(17) C5 O4 1.457(2) C5 C6 1.508(2) C6 C7 1.522(2) C7 C8 1.487(2) C8 C9 1.510(2) C9 C13 1.5157(19) C11 O2 1.1998(18) C11 O3 1.3370(18) C12 O3 1.445(2) C13 C14 1.3970(19) C13 C18 1.404(2) C14 O5 1.3670(17) C14 C15 1.397(2) C15 C16 1.384(2) C16 O6 1.3700(17) C16 C17 1.389(2) C17 C18 1.382(2) C18 O7 1.3672(16) C19 O5 1.4150(19) C20 O6 1.414(2) C21 O7 1.4234(19) 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 -50.3(2) C9 C1 C2 O1 -173.04(15) C11 C1 C2 C3 133.55(13) C9 C1 C2 C3 10.81(15) O1 C2 C3 C8 179.24(15) C1 C2 C3 C8 -4.70(16) O1 C2 C3 O4 -3.7(2) C1 C2 C3 O4 172.38(12) O4 C5 C6 C7 -59.8(2) C5 C6 C7 C8 47.74(18) O4 C3 C8 C7 -3.0(2) C2 C3 C8 C7 173.81(13) O4 C3 C8 C9 179.26(13) C2 C3 C8 C9 -3.90(17) C6 C7 C8 C3 -19.2(2) C6 C7 C8 C9 158.21(13) C3 C8 C9 C13 135.79(13) C7 C8 C9 C13 -41.82(19) C3 C8 C9 C1 10.43(15) C7 C8 C9 C1 -167.18(14) C11 C1 C9 C8 -136.97(12) C2 C1 C9 C8 -12.45(14) C11 C1 C9 C13 97.58(14) C2 C1 C9 C13 -137.90(12) C2 C1 C11 O2 -34.2(2) C9 C1 C11 O2 85.12(18) C2 C1 C11 O3 148.33(12) C9 C1 C11 O3 -92.32(14) C8 C9 C13 C14 128.06(14) C1 C9 C13 C14 -113.25(15) C8 C9 C13 C18 -52.02(18) C1 C9 C13 C18 66.67(17) C18 C13 C14 O5 -179.00(12) C9 C13 C14 O5 0.92(19) C18 C13 C14 C15 1.5(2) C9 C13 C14 C15 -178.57(13) O5 C14 C15 C16 -179.44(14) C13 C14 C15 C16 0.0(2) C14 C15 C16 O6 179.80(14) C14 C15 C16 C17 -1.3(2) O6 C16 C17 C18 179.99(13) C15 C16 C17 C18 1.0(2) C16 C17 C18 O7 179.87(13) C16 C17 C18 C13 0.6(2) C14 C13 C18 O7 178.87(12) C9 C13 C18 O7 -1.05(19) C14 C13 C18 C17 -1.8(2) C9 C13 C18 C17 178.23(13) O2 C11 O3 C12 -3.2(2) C1 C11 O3 C12 174.28(13) C8 C3 O4 C5 -5.6(2) C2 C3 O4 C5 177.82(13) C6 C5 O4 C3 36.88(19) C13 C14 O5 C19 169.06(15) C15 C14 O5 C19 -11.5(2) C15 C16 O6 C20 -12.9(3) C17 C16 O6 C20 168.2(2) C17 C18 O7 C21 11.8(2) C13 C18 O7 C21 -168.91(14)