#------------------------------------------------------------------------------ #$Date: 2012-02-26 04:28:18 +0200 (Sun, 26 Feb 2012) $ #$Revision: 35484 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/1502167.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_1502167 loop_ _publ_author_name 'Xu, Tao' 'Li, Chuang-chuang' 'Yang, Zhen' _publ_section_title ; A concise approach for the total synthesis of pseudolaric acid A. ; _journal_issue 10 _journal_name_full 'Organic letters' _journal_page_first 2630 _journal_page_last 2633 _journal_volume 13 _journal_year 2011 _chemical_formula_sum 'C18 H34 O3 Si' _chemical_formula_weight 326.54 _chemical_name_systematic ; ? ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/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 99.86(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 25.618(5) _cell_length_b 11.614(2) _cell_length_c 13.245(3) _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.39 _cell_volume 3882.5(14) _computing_cell_refinement Rapid-AUTO _computing_data_collection 'Rapid-AUTO (Rigaku,2000)' _computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)' _computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)' _computing_publication_material SHELXL-97,(Sheldrick,1997) _computing_structure_refinement SHELXL-97,(Sheldrick,1997) _computing_structure_solution SHELXS-97,(Sheldrick,1997) _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 10.00 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method \W _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 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0846 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 8364 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 2.39 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_T_max 0.9743 _exptl_absorpt_correction_T_min 0.9618 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ; HIGASHI, T. (1995). Abscor-Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation,Tokyo,Japan. ; _exptl_crystal_density_diffrn 1.117 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.302 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.048 _refine_ls_extinction_coef 0.0079(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment none _refine_ls_matrix_type full _refine_ls_number_parameters 207 _refine_ls_number_reflns 4444 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.017 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0458 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0953 _refine_ls_wR_factor_ref 0.0992 _reflns_number_gt 2483 _reflns_number_total 4444 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file ol200741j_si_002.cif _[local]_cod_data_source_block xt0 _[local]_cod_cif_authors_sg_H-M C2/c _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Empirical' changed to 'empirical' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 3882.7(13) _cod_database_code 1502167 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 _atom_site_refinement_flags C1 C 0.37193(6) 0.75893(15) 0.88348(12) 0.0269(4) Uani 1 1 d . C2 C 0.33911(7) 0.84067(15) 0.93823(13) 0.0350(4) Uani 1 1 d . H2A H 0.3029 0.8404 0.9016 0.042 Uiso 1 1 calc R H2B H 0.3386 0.8108 1.0065 0.042 Uiso 1 1 calc R C3 C 0.35859(8) 0.96502(15) 0.94793(14) 0.0436(5) Uani 1 1 d . H3A H 0.3372 1.0053 0.9904 0.052 Uiso 1 1 calc R H3B H 0.3946 0.9637 0.9856 0.052 Uiso 1 1 calc R C4 C 0.35883(6) 1.03754(16) 0.85303(14) 0.0356(4) Uani 1 1 d . C5 C 0.33993(8) 1.15877(17) 0.86410(16) 0.0557(6) Uani 1 1 d . H5A H 0.3435 1.2022 0.8040 0.084 Uiso 1 1 calc R H5B H 0.3608 1.1939 0.9232 0.084 Uiso 1 1 calc R H5C H 0.3034 1.1575 0.8722 0.084 Uiso 1 1 calc R C6 C 0.37702(7) 1.00539(16) 0.76955(14) 0.0391(5) Uani 1 1 d . H6 H 0.3758 1.0616 0.7192 0.047 Uiso 1 1 calc R C7 C 0.39933(7) 0.89150(15) 0.74431(13) 0.0350(4) Uani 1 1 d . H7A H 0.4351 0.8851 0.7823 0.042 Uiso 1 1 calc R H7B H 0.4017 0.8912 0.6720 0.042 Uiso 1 1 calc R C8 C 0.36827(6) 0.78496(14) 0.76698(12) 0.0275(4) Uani 1 1 d . C9 C 0.31003(6) 0.79927(15) 0.71487(12) 0.0312(4) Uani 1 1 d . H9A H 0.2897 0.7339 0.7320 0.037 Uiso 1 1 calc R H9B H 0.2955 0.8681 0.7411 0.037 Uiso 1 1 calc R C10 C 0.39069(7) 0.67358(15) 0.72952(13) 0.0365(5) Uani 1 1 d . H10A H 0.3821 0.6674 0.6555 0.044 Uiso 1 1 calc R H10B H 0.4289 0.6705 0.7500 0.044 Uiso 1 1 calc R C11 C 0.36387(7) 0.57795(15) 0.78124(14) 0.0398(5) Uani 1 1 d . H11A H 0.3849 0.5081 0.7868 0.048 Uiso 1 1 calc R H11B H 0.3290 0.5612 0.7428 0.048 Uiso 1 1 calc R C12 C 0.35991(6) 0.62613(14) 0.88881(13) 0.0295(4) Uani 1 1 d . H12 H 0.3910 0.5945 0.9338 0.035 Uiso 1 1 calc R C13 C 0.49356(9) 0.8789(2) 1.09961(18) 0.0844(9) Uani 1 1 d . H13A H 0.5111 0.9223 1.0535 0.127 Uiso 1 1 calc R H13B H 0.5185 0.8601 1.1601 0.127 Uiso 1 1 calc R H13C H 0.4653 0.9240 1.1183 0.127 Uiso 1 1 calc R C14 C 0.52141(9) 0.6613(3) 0.9999(2) 0.1153(12) Uani 1 1 d . H14A H 0.5078 0.5947 0.9612 0.173 Uiso 1 1 calc R H14B H 0.5449 0.6374 1.0607 0.173 Uiso 1 1 calc R H14C H 0.5404 0.7086 0.9590 0.173 Uiso 1 1 calc R C15 C 0.43400(9) 0.6645(2) 1.13083(16) 0.0723(7) Uani 1 1 d . H15A H 0.4018 0.7030 1.1391 0.109 Uiso 1 1 calc R H15B H 0.4576 0.6621 1.1955 0.109 Uiso 1 1 calc R H15C H 0.4260 0.5875 1.1069 0.109 Uiso 1 1 calc R C16 C 0.31217(6) 0.58178(15) 0.93486(13) 0.0321(4) Uani 1 1 d . H16 H 0.3139 0.6188 1.0018 0.039 Uiso 1 1 calc R C17 C 0.25673(6) 0.60303(17) 0.87476(15) 0.0449(5) Uani 1 1 d . H17A H 0.2543 0.5722 0.8069 0.067 Uiso 1 1 calc R H17B H 0.2499 0.6843 0.8708 0.067 Uiso 1 1 calc R H17C H 0.2311 0.5660 0.9088 0.067 Uiso 1 1 calc R C18 C 0.32002(7) 0.45344(16) 0.95409(15) 0.0443(5) Uani 1 1 d . H18A H 0.3161 0.4140 0.8887 0.053 Uiso 1 1 calc R H18B H 0.3558 0.4403 0.9898 0.053 Uiso 1 1 calc R O3 O 0.28360(5) 0.40493(12) 1.01294(9) 0.0497(4) Uani 1 1 d . H3 H 0.2567 0.3843 0.9744 0.074 Uiso 1 1 calc R O1 O 0.30478(5) 0.80781(11) 0.60580(9) 0.0419(3) Uani 1 1 d . H1 H 0.3027 0.7431 0.5807 0.063 Uiso 1 1 calc R O2 O 0.42665(4) 0.77545(11) 0.92927(8) 0.0376(3) Uani 1 1 d . Si1 Si 0.46620(2) 0.74414(5) 1.03582(4) 0.04489(18) Uani 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 0.0263(8) 0.0294(11) 0.0250(9) -0.0015(8) 0.0041(7) -0.0024(8) C2 0.0474(11) 0.0294(11) 0.0308(10) -0.0017(8) 0.0143(8) -0.0019(9) C3 0.0603(13) 0.0304(12) 0.0400(11) -0.0058(9) 0.0085(9) 0.0001(10) C4 0.0359(10) 0.0287(12) 0.0406(11) -0.0011(9) 0.0019(8) -0.0038(8) C5 0.0759(15) 0.0336(13) 0.0573(14) -0.0005(11) 0.0102(11) 0.0030(11) C6 0.0434(11) 0.0330(12) 0.0406(12) 0.0065(9) 0.0066(9) -0.0071(9) C7 0.0382(10) 0.0377(12) 0.0305(10) 0.0045(9) 0.0100(8) -0.0020(9) C8 0.0290(9) 0.0284(11) 0.0262(9) -0.0006(7) 0.0080(7) -0.0010(7) C9 0.0383(10) 0.0294(11) 0.0255(9) -0.0012(8) 0.0041(7) 0.0003(8) C10 0.0411(10) 0.0374(12) 0.0327(10) -0.0030(9) 0.0109(8) 0.0049(9) C11 0.0489(11) 0.0309(12) 0.0420(11) -0.0045(9) 0.0146(9) 0.0060(9) C12 0.0298(9) 0.0258(11) 0.0331(10) -0.0002(8) 0.0055(7) 0.0020(8) C13 0.0855(18) 0.085(2) 0.0673(17) 0.0093(15) -0.0293(13) -0.0373(15) C14 0.0743(19) 0.157(3) 0.114(3) 0.019(2) 0.0147(18) 0.056(2) C15 0.0737(16) 0.093(2) 0.0433(14) 0.0200(13) -0.0093(11) -0.0250(14) C16 0.0346(10) 0.0284(11) 0.0335(10) 0.0003(8) 0.0064(8) -0.0029(8) C17 0.0345(10) 0.0431(13) 0.0581(13) 0.0120(10) 0.0104(9) -0.0034(9) C18 0.0468(11) 0.0361(13) 0.0495(12) 0.0117(10) 0.0065(10) -0.0037(9) O3 0.0550(9) 0.0458(10) 0.0451(8) 0.0142(7) -0.0001(7) -0.0192(7) O1 0.0569(8) 0.0400(8) 0.0259(7) -0.0015(6) -0.0012(6) 0.0038(7) O2 0.0309(7) 0.0481(9) 0.0313(7) 0.0029(6) -0.0017(5) -0.0088(6) Si1 0.0345(3) 0.0561(4) 0.0411(3) 0.0083(3) -0.0021(2) -0.0045(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' Si Si 0.0817 0.0704 '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 O2 C1 C2 106.95(14) O2 C1 C8 106.26(12) C2 C1 C8 113.81(14) O2 C1 C12 107.14(13) C2 C1 C12 117.27(13) C8 C1 C12 104.76(13) C3 C2 C1 115.38(14) C3 C2 H2A 108.4 C1 C2 H2A 108.4 C3 C2 H2B 108.4 C1 C2 H2B 108.4 H2A C2 H2B 107.5 C4 C3 C2 120.29(15) C4 C3 H3A 107.3 C2 C3 H3A 107.3 C4 C3 H3B 107.3 C2 C3 H3B 107.3 H3A C3 H3B 106.9 C6 C4 C5 120.68(17) C6 C4 C3 126.03(17) C5 C4 C3 113.12(16) C4 C5 H5A 109.5 C4 C5 H5B 109.5 H5A C5 H5B 109.5 C4 C5 H5C 109.5 H5A C5 H5C 109.5 H5B C5 H5C 109.5 C4 C6 C7 129.48(17) C4 C6 H6 115.3 C7 C6 H6 115.3 C6 C7 C8 116.01(14) C6 C7 H7A 108.3 C8 C7 H7A 108.3 C6 C7 H7B 108.3 C8 C7 H7B 108.3 H7A C7 H7B 107.4 C7 C8 C10 112.54(13) C7 C8 C9 108.74(14) C10 C8 C9 109.50(14) C7 C8 C1 113.96(14) C10 C8 C1 101.20(13) C9 C8 C1 110.70(13) O1 C9 C8 112.07(14) O1 C9 H9A 109.2 C8 C9 H9A 109.2 O1 C9 H9B 109.2 C8 C9 H9B 109.2 H9A C9 H9B 107.9 C11 C10 C8 104.26(13) C11 C10 H10A 110.9 C8 C10 H10A 110.9 C11 C10 H10B 110.9 C8 C10 H10B 110.9 H10A C10 H10B 108.9 C10 C11 C12 104.76(14) C10 C11 H11A 110.8 C12 C11 H11A 110.8 C10 C11 H11B 110.8 C12 C11 H11B 110.8 H11A C11 H11B 108.9 C16 C12 C11 115.04(14) C16 C12 C1 121.17(13) C11 C12 C1 105.54(13) C16 C12 H12 104.5 C11 C12 H12 104.5 C1 C12 H12 104.5 Si1 C13 H13A 109.5 Si1 C13 H13B 109.5 H13A C13 H13B 109.5 Si1 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 Si1 C14 H14A 109.5 Si1 C14 H14B 109.5 H14A C14 H14B 109.5 Si1 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 Si1 C15 H15A 109.5 Si1 C15 H15B 109.5 H15A C15 H15B 109.5 Si1 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C18 C16 C17 109.33(14) C18 C16 C12 107.59(14) C17 C16 C12 117.99(14) C18 C16 H16 107.1 C17 C16 H16 107.1 C12 C16 H16 107.1 C16 C17 H17A 109.5 C16 C17 H17B 109.5 H17A C17 H17B 109.5 C16 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 O3 C18 C16 113.45(15) O3 C18 H18A 108.9 C16 C18 H18A 108.9 O3 C18 H18B 108.9 C16 C18 H18B 108.9 H18A C18 H18B 107.7 C18 O3 H3 109.5 C9 O1 H1 109.5 C1 O2 Si1 138.55(11) O2 Si1 C14 106.50(11) O2 Si1 C13 109.61(9) C14 Si1 C13 108.15(14) O2 Si1 C15 114.42(8) C14 Si1 C15 111.35(14) C13 Si1 C15 106.68(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O2 1.4417(17) C1 C2 1.531(2) C1 C8 1.559(2) C1 C12 1.577(2) C2 C3 1.526(2) C2 H2A 0.9700 C2 H2B 0.9700 C3 C4 1.514(2) C3 H3A 0.9700 C3 H3B 0.9700 C4 C6 1.325(2) C4 C5 1.504(3) C5 H5A 0.9600 C5 H5B 0.9600 C5 H5C 0.9600 C6 C7 1.501(2) C6 H6 0.9300 C7 C8 1.529(2) C7 H7A 0.9700 C7 H7B 0.9700 C8 C10 1.532(2) C8 C9 1.542(2) C9 O1 1.4312(19) C9 H9A 0.9700 C9 H9B 0.9700 C10 C11 1.528(2) C10 H10A 0.9700 C10 H10B 0.9700 C11 C12 1.550(2) C11 H11A 0.9700 C11 H11B 0.9700 C12 C16 1.545(2) C12 H12 0.9800 C13 Si1 1.858(2) C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 C14 Si1 1.839(3) C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 0.9600 C15 Si1 1.864(2) C15 H15A 0.9600 C15 H15B 0.9600 C15 H15C 0.9600 C16 C18 1.520(2) C16 C17 1.525(2) C16 H16 0.9800 C17 H17A 0.9600 C17 H17B 0.9600 C17 H17C 0.9600 C18 O3 1.430(2) C18 H18A 0.9700 C18 H18B 0.9700 O3 H3 0.8200 O1 H1 0.8200 O2 Si1 1.6314(13)