#------------------------------------------------------------------------------ #$Date: 2014-07-12 00:06:05 +0300 (Sat, 12 Jul 2014) $ #$Revision: 120077 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/11/44/4114435.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_4114435 loop_ _publ_author_name 'Fredrik P. Marms\"ater' 'Graham K. Murphy' 'F. G. West' _publ_contact_author_address ; Department of Chemistry University of Alberta Edmonton, Alberta T6G 2G2 Canada ; _publ_contact_author_email frederick.west@ualberta.ca _publ_contact_author_fax 1(780)4928231 _publ_contact_author_name 'Dr. Frederick G. West' _publ_contact_author_phone 1(780)4928187 _publ_section_title ; Cyclooctanoid Ring Systems from Mixed Acetals via Heteroatom-Assisted [1,2]-Shift of Oxonium Ylides ; _journal_name_full 'Journal of the American Chemical Society' _journal_page_first 14724 _journal_page_last 14725 _journal_volume 125 _journal_year 2003 _chemical_formula_sum 'C20 H26 O5 S' _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method 'manual editing of SHELXL template' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 12.6104(14) _cell_length_b 16.2906(19) _cell_length_c 17.927(2) _cell_measurement_reflns_used 5391 _cell_measurement_temperature 193(2) _cell_measurement_theta_max 25.376 _cell_measurement_theta_min 2.500 _cell_volume 3682.8(7) _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 193(2) _diffrn_detector_area_resol_mean 8.192 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _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 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 19515 _diffrn_reflns_theta_full 26.45 _diffrn_reflns_theta_max 26.45 _diffrn_reflns_theta_min 2.27 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.204 _exptl_absorpt_correction_T_max 0.9838 _exptl_absorpt_correction_T_min 0.8685 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.365 _exptl_crystal_description needle _exptl_crystal_F_000 1616 _exptl_crystal_size_max 0.71 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.428 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 3778 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0481 _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^)+(0.0510P)^2^+1.6654P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1064 _refine_ls_wR_factor_ref 0.1143 _reflns_number_gt 2978 _reflns_number_total 3778 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ja0387249si20030925_114602_2.cif _[local]_cod_data_source_block compound(11) _cod_database_code 4114435 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, 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 S S 0.33151(4) 0.17193(3) 0.02733(3) 0.03039(15) Uani 1 1 d . O1 O 0.37246(11) 0.32015(8) -0.13225(7) 0.0278(3) Uani 1 1 d . O2 O 0.54393(12) 0.20819(10) -0.18345(9) 0.0416(4) Uani 1 1 d . O3 O 0.42403(13) 0.10672(9) -0.16530(10) 0.0433(4) Uani 1 1 d . O4 O 0.31554(14) 0.24171(9) 0.07553(8) 0.0429(4) Uani 1 1 d . O5 O 0.43439(12) 0.13420(10) 0.02561(9) 0.0447(4) Uani 1 1 d . C1 C 0.32565(17) 0.31029(13) -0.20692(11) 0.0311(5) Uani 1 1 d . C2 C 0.35644(19) 0.38658(14) -0.25118(13) 0.0415(6) Uani 1 1 d . H2A H 0.3475 0.3770 -0.3054 0.050 Uiso 1 1 calc R H2B H 0.4312 0.4017 -0.2413 0.050 Uiso 1 1 calc R C3 C 0.2816(2) 0.45394(15) -0.22429(17) 0.0543(7) Uani 1 1 d . H3A H 0.2546 0.4862 -0.2670 0.065 Uiso 1 1 calc R H3B H 0.3187 0.4915 -0.1896 0.065 Uiso 1 1 calc R C4 C 0.19001(19) 0.40997(15) -0.18428(15) 0.0450(6) Uani 1 1 d . H4A H 0.1927 0.4205 -0.1299 0.054 Uiso 1 1 calc R H4B H 0.1208 0.4291 -0.2037 0.054 Uiso 1 1 calc R C5 C 0.20571(17) 0.31874(13) -0.20060(12) 0.0340(5) Uani 1 1 d . H5 H 0.1760 0.3084 -0.2514 0.041 Uiso 1 1 calc R C6 C 0.14938(17) 0.25989(14) -0.14734(12) 0.0362(5) Uani 1 1 d . H6A H 0.1491 0.2047 -0.1704 0.043 Uiso 1 1 calc R H6B H 0.0746 0.2777 -0.1427 0.043 Uiso 1 1 calc R C7 C 0.19617(16) 0.25224(14) -0.06845(11) 0.0321(5) Uani 1 1 d . H7A H 0.2126 0.3078 -0.0492 0.038 Uiso 1 1 calc R H7B H 0.1425 0.2273 -0.0351 0.038 Uiso 1 1 calc R C8 C 0.29672(16) 0.20018(12) -0.06663(11) 0.0274(4) Uani 1 1 d . H8 H 0.2817 0.1484 -0.0947 0.033 Uiso 1 1 calc R C9 C 0.39500(16) 0.24125(12) -0.10333(11) 0.0273(4) Uani 1 1 d . H9 H 0.4535 0.2454 -0.0659 0.033 Uiso 1 1 calc R C10 C 0.43443(17) 0.19305(13) -0.17203(12) 0.0336(5) Uani 1 1 d . C11 C 0.36832(19) 0.22817(14) -0.23513(12) 0.0397(6) Uani 1 1 d . H11A H 0.3092 0.1907 -0.2477 0.048 Uiso 1 1 calc R H11B H 0.4124 0.2363 -0.2802 0.048 Uiso 1 1 calc R C12 C 0.23797(15) 0.09549(12) 0.05032(11) 0.0254(4) Uani 1 1 d . C13 C 0.14715(16) 0.11612(12) 0.08932(11) 0.0296(5) Uani 1 1 d . H13 H 0.1358 0.1709 0.1056 0.035 Uiso 1 1 calc R C14 C 0.07331(17) 0.05580(13) 0.10426(12) 0.0327(5) Uani 1 1 d . H14 H 0.0105 0.0698 0.1306 0.039 Uiso 1 1 calc R C15 C 0.08888(16) -0.02498(12) 0.08163(12) 0.0302(5) Uani 1 1 d . C16 C 0.18041(18) -0.04393(13) 0.04282(14) 0.0375(5) Uani 1 1 d . H16 H 0.1922 -0.0988 0.0270 0.045 Uiso 1 1 calc R C17 C 0.25498(17) 0.01558(13) 0.02674(13) 0.0352(5) Uani 1 1 d . H17 H 0.3174 0.0018 -0.0002 0.042 Uiso 1 1 calc R C18 C 0.00754(18) -0.08986(14) 0.09903(15) 0.0440(6) Uani 1 1 d . H18A H 0.0327 -0.1432 0.0810 0.053 Uiso 1 1 calc R H18B H -0.0595 -0.0761 0.0744 0.053 Uiso 1 1 calc R H18C H -0.0036 -0.0925 0.1531 0.053 Uiso 1 1 calc R C19 C 0.5975(2) 0.14536(16) -0.14334(17) 0.0541(7) Uani 1 1 d . H19A H 0.6101 0.1622 -0.0910 0.065 Uiso 1 1 calc R H19B H 0.6665 0.1323 -0.1669 0.065 Uiso 1 1 calc R C20 C 0.5243(2) 0.07328(16) -0.14684(19) 0.0594(8) Uani 1 1 d . H20A H 0.5478 0.0338 -0.1854 0.071 Uiso 1 1 calc R H20B H 0.5214 0.0448 -0.0981 0.071 Uiso 1 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 S 0.0361(3) 0.0300(3) 0.0250(3) 0.0053(2) -0.0058(2) -0.0106(2) O1 0.0347(8) 0.0262(7) 0.0223(7) 0.0019(6) -0.0057(6) -0.0098(6) O2 0.0373(9) 0.0415(9) 0.0459(10) 0.0047(8) 0.0108(7) -0.0057(7) O3 0.0459(10) 0.0274(8) 0.0566(11) -0.0053(7) 0.0072(8) -0.0049(7) O4 0.0679(11) 0.0331(8) 0.0277(8) 0.0006(7) -0.0083(7) -0.0189(8) O5 0.0335(9) 0.0514(10) 0.0491(10) 0.0186(8) -0.0069(7) -0.0084(7) C1 0.0398(12) 0.0328(11) 0.0206(10) 0.0012(8) -0.0057(8) -0.0121(9) C2 0.0457(14) 0.0465(14) 0.0322(12) 0.0138(10) -0.0082(10) -0.0186(11) C3 0.0573(16) 0.0359(14) 0.0697(19) 0.0142(13) -0.0153(14) -0.0141(12) C4 0.0497(14) 0.0389(13) 0.0465(15) 0.0072(11) -0.0083(11) -0.0010(11) C5 0.0370(12) 0.0373(12) 0.0277(11) 0.0053(9) -0.0111(9) -0.0126(9) C6 0.0319(11) 0.0422(13) 0.0347(12) 0.0084(10) -0.0073(9) -0.0106(10) C7 0.0303(11) 0.0377(12) 0.0282(11) 0.0061(9) -0.0006(8) -0.0081(9) C8 0.0346(11) 0.0284(11) 0.0193(10) 0.0019(8) -0.0034(8) -0.0094(8) C9 0.0298(11) 0.0260(10) 0.0261(10) 0.0031(8) -0.0033(8) -0.0086(8) C10 0.0367(12) 0.0296(11) 0.0346(12) -0.0004(9) 0.0051(9) -0.0106(9) C11 0.0475(14) 0.0447(14) 0.0268(12) -0.0060(10) 0.0001(10) -0.0089(11) C12 0.0307(11) 0.0217(10) 0.0240(10) 0.0038(8) -0.0006(8) -0.0036(8) C13 0.0396(12) 0.0221(10) 0.0270(10) -0.0005(8) 0.0029(9) 0.0027(8) C14 0.0333(12) 0.0315(11) 0.0332(12) 0.0029(9) 0.0084(9) 0.0058(9) C15 0.0300(11) 0.0245(10) 0.0360(12) 0.0067(9) 0.0006(9) 0.0004(8) C16 0.0400(13) 0.0200(10) 0.0526(15) -0.0029(10) 0.0104(10) 0.0032(9) C17 0.0334(12) 0.0290(11) 0.0433(13) -0.0013(10) 0.0128(9) 0.0036(9) C18 0.0378(13) 0.0329(12) 0.0612(16) 0.0084(12) 0.0080(11) -0.0041(10) C19 0.0419(14) 0.0462(15) 0.0741(19) 0.0046(14) 0.0024(13) 0.0007(12) C20 0.0526(17) 0.0380(15) 0.088(2) 0.0017(14) 0.0143(15) 0.0052(12) 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' S S 0.1246 0.1234 '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 O5 S O4 118.46(10) O5 S C12 107.88(9) O4 S C12 108.85(9) O5 S C8 108.03(10) O4 S C8 108.97(9) C12 S C8 103.65(9) C9 O1 C1 108.35(14) C10 O2 C19 105.35(17) C20 O3 C10 108.61(17) O1 C1 C5 108.71(17) O1 C1 C2 106.39(16) C5 C1 C2 102.59(18) O1 C1 C11 104.79(17) C5 C1 C11 116.97(17) C2 C1 C11 116.86(19) C1 C2 C3 105.33(19) C2 C3 C4 106.09(19) C5 C4 C3 105.5(2) C1 C5 C4 103.35(17) C1 C5 C6 116.84(18) C4 C5 C6 115.5(2) C5 C6 C7 116.56(17) C8 C7 C6 112.56(18) C7 C8 C9 114.48(16) C7 C8 S 111.38(14) C9 C8 S 108.16(13) O1 C9 C10 103.56(16) O1 C9 C8 112.70(16) C10 C9 C8 112.07(16) O2 C10 O3 105.97(17) O2 C10 C11 111.22(18) O3 C10 C11 112.75(18) O2 C10 C9 109.91(17) O3 C10 C9 114.02(17) C11 C10 C9 103.07(17) C10 C11 C1 106.07(17) C13 C12 C17 120.71(18) C13 C12 S 120.02(15) C17 C12 S 119.24(15) C14 C13 C12 118.93(18) C13 C14 C15 121.46(19) C16 C15 C14 118.41(19) C16 C15 C18 121.08(19) C14 C15 C18 120.51(19) C17 C16 C15 121.12(19) C16 C17 C12 119.37(19) O2 C19 C20 104.5(2) O3 C20 C19 105.0(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S O5 1.4359(17) S O4 1.4419(16) S C12 1.7640(19) S C8 1.801(2) O1 C9 1.415(2) O1 C1 1.472(2) O2 C10 1.418(3) O2 C19 1.422(3) O3 C20 1.416(3) O3 C10 1.418(3) C1 C5 1.523(3) C1 C2 1.525(3) C1 C11 1.528(3) C2 C3 1.525(4) C3 C4 1.537(4) C4 C5 1.528(3) C5 C6 1.528(3) C6 C7 1.537(3) C7 C8 1.526(3) C8 C9 1.554(3) C9 C10 1.543(3) C10 C11 1.517(3) C12 C13 1.383(3) C12 C17 1.386(3) C13 C14 1.380(3) C14 C15 1.391(3) C15 C16 1.383(3) C15 C18 1.505(3) C16 C17 1.381(3) C19 C20 1.495(4) 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 C9 O1 C1 C5 99.82(18) C9 O1 C1 C2 -150.33(17) C9 O1 C1 C11 -26.0(2) O1 C1 C2 C3 -78.0(2) C5 C1 C2 C3 36.1(2) C11 C1 C2 C3 165.44(19) C1 C2 C3 C4 -16.7(3) C2 C3 C4 C5 -9.1(3) O1 C1 C5 C4 70.8(2) C2 C1 C5 C4 -41.5(2) C11 C1 C5 C4 -170.82(18) O1 C1 C5 C6 -57.2(2) C2 C1 C5 C6 -169.56(19) C11 C1 C5 C6 61.2(3) C3 C4 C5 C1 31.4(2) C3 C4 C5 C6 160.22(19) C1 C5 C6 C7 49.2(3) C4 C5 C6 C7 -72.7(3) C5 C6 C7 C8 -76.3(3) C6 C7 C8 C9 70.7(2) C6 C7 C8 S -166.16(14) O5 S C8 C7 -171.38(14) O4 S C8 C7 -41.46(16) C12 S C8 C7 74.33(15) O5 S C8 C9 -44.75(16) O4 S C8 C9 85.17(15) C12 S C8 C9 -159.03(14) C1 O1 C9 C10 38.10(19) C1 O1 C9 C8 -83.22(19) C7 C8 C9 O1 -0.3(2) S C8 C9 O1 -125.08(15) C7 C8 C9 C10 -116.61(19) S C8 C9 C10 118.57(16) C19 O2 C10 O3 -32.0(2) C19 O2 C10 C11 -154.9(2) C19 O2 C10 C9 91.6(2) C20 O3 C10 O2 19.9(2) C20 O3 C10 C11 141.8(2) C20 O3 C10 C9 -101.1(2) O1 C9 C10 O2 84.02(19) C8 C9 C10 O2 -154.24(17) O1 C9 C10 O3 -157.18(17) C8 C9 C10 O3 -35.4(2) O1 C9 C10 C11 -34.62(19) C8 C9 C10 C11 87.12(19) O2 C10 C11 C1 -98.9(2) O3 C10 C11 C1 142.26(18) C9 C10 C11 C1 18.9(2) O1 C1 C11 C10 2.7(2) C5 C1 C11 C10 -117.7(2) C2 C1 C11 C10 120.1(2) O5 S C12 C13 149.40(17) O4 S C12 C13 19.66(19) C8 S C12 C13 -96.21(18) O5 S C12 C17 -32.7(2) O4 S C12 C17 -162.45(17) C8 S C12 C17 81.68(19) C17 C12 C13 C14 -0.2(3) S C12 C13 C14 177.65(16) C12 C13 C14 C15 0.6(3) C13 C14 C15 C16 -0.6(3) C13 C14 C15 C18 179.6(2) C14 C15 C16 C17 0.0(3) C18 C15 C16 C17 179.9(2) C15 C16 C17 C12 0.4(4) C13 C12 C17 C16 -0.3(3) S C12 C17 C16 -178.17(18) C10 O2 C19 C20 31.2(3) C10 O3 C20 C19 -0.5(3) O2 C19 C20 O3 -18.9(3) _journal_paper_doi 10.1021/ja0387249