#------------------------------------------------------------------------------ #$Date: 2012-03-07 14:49:24 +0200 (Wed, 07 Mar 2012) $ #$Revision: 39520 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/42/1504229.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_1504229 loop_ _publ_author_name 'Webster, Robert' 'Lautens, Mark' _publ_section_title ; Conformational effects in diastereoselective aryne Diels-Alder reactions: synthesis of benzo-fused [2.2.1] heterobicycles. ; _journal_issue 20 _journal_name_full 'Organic letters' _journal_page_first 4688 _journal_page_last 4691 _journal_volume 11 _journal_year 2009 _chemical_absolute_configuration ad _chemical_formula_moiety 'C23 H27 N O4 S' _chemical_formula_sum 'C23 H27 N O4 S' _chemical_formula_weight 413.52 _chemical_name_systematic ; ? ; _space_group_IT_number 92 _symmetry_cell_setting tetragonal _symmetry_space_group_name_Hall 'P 4abw 2nw' _symmetry_space_group_name_H-M 'P 41 21 2' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 10.8340(2) _cell_length_b 10.8340(2) _cell_length_c 36.3990(9) _cell_measurement_reflns_used 20946 _cell_measurement_temperature 150(1) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.7 _cell_volume 4272.35(15) _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_data_reduction Denzo-SMN _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL V6.1' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _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 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0575 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 20946 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 2.66 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_correction_T_min 0.909 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1760 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.192 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.041 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 266 _refine_ls_number_reflns 4888 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.017 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0419 _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^)+(0.0481P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0848 _refine_ls_wR_factor_ref 0.0947 _reflns_number_gt 3685 _reflns_number_total 4888 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ol9019869_si_008.cif _[local]_cod_data_source_block k08226 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 1504229 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, -z+3/4' '-x+1/2, y+1/2, -z+1/4' '-y, -x, -z+1/2' 'y, x, -z' 'y+1/2, -x+1/2, z+3/4' '-y+1/2, x+1/2, z+1/4' 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 S1 S 0.24849(5) 0.28025(4) 0.411763(13) 0.02730(13) Uani 1 1 d . O1 O 0.11916(12) 0.64843(12) 0.46723(4) 0.0313(3) Uani 1 1 d . N1 N 0.10968(14) 0.24314(14) 0.43069(4) 0.0255(4) Uani 1 1 d . C1 C 0.08215(18) 0.44228(17) 0.46215(5) 0.0251(4) Uani 1 1 d . O2 O -0.08187(12) 0.31774(12) 0.44200(4) 0.0325(3) Uani 1 1 d . C2 C 0.01313(18) 0.56782(18) 0.46271(5) 0.0283(5) Uani 1 1 d . O3 O 0.34261(12) 0.28058(13) 0.43938(4) 0.0347(3) Uani 1 1 d . C3 C -0.0419(2) 0.57973(17) 0.50141(5) 0.0302(5) Uani 1 1 d . O4 O 0.23529(14) 0.38834(12) 0.38970(4) 0.0369(4) Uani 1 1 d . C4 C -0.1609(2) 0.5846(2) 0.51463(7) 0.0421(6) Uani 1 1 d . H4A H -0.2299 0.5763 0.4988 0.051 Uiso 1 1 calc R C5 C -0.1757(2) 0.6025(2) 0.55245(7) 0.0517(7) Uani 1 1 d . H5A H -0.2566 0.6052 0.5625 0.062 Uiso 1 1 calc R C6 C -0.0761(3) 0.6161(2) 0.57546(7) 0.0513(7) Uani 1 1 d . H6A H -0.0893 0.6297 0.6009 0.062 Uiso 1 1 calc R C7 C 0.0448(2) 0.61022(19) 0.56180(6) 0.0418(6) Uani 1 1 d . H7A H 0.1140 0.6182 0.5777 0.050 Uiso 1 1 calc R C8 C 0.0597(2) 0.59246(18) 0.52473(6) 0.0330(5) Uani 1 1 d . C9 C 0.17189(19) 0.58757(19) 0.49930(6) 0.0313(5) Uani 1 1 d . C10 C 0.17673(18) 0.45420(18) 0.48492(5) 0.0276(5) Uani 1 1 d . H10 H 0.2357 0.3927 0.4911 0.033 Uiso 1 1 calc R C11 C -0.0656(2) 0.6008(2) 0.43042(6) 0.0384(5) Uani 1 1 d . H11A H -0.0992 0.6840 0.4338 0.058 Uiso 1 1 calc R H11B H -0.1335 0.5415 0.4283 0.058 Uiso 1 1 calc R H11C H -0.0156 0.5986 0.4080 0.058 Uiso 1 1 calc R C12 C 0.2908(2) 0.6450(2) 0.51168(7) 0.0425(6) Uani 1 1 d . H12A H 0.2762 0.7314 0.5184 0.064 Uiso 1 1 calc R H12B H 0.3512 0.6412 0.4917 0.064 Uiso 1 1 calc R H12C H 0.3225 0.6000 0.5330 0.064 Uiso 1 1 calc R C13 C 0.02963(19) 0.33308(18) 0.44439(5) 0.0267(5) Uani 1 1 d . C14 C 0.2600(2) 0.14573(18) 0.38354(6) 0.0332(5) Uani 1 1 d . H14A H 0.2561 0.1690 0.3573 0.040 Uiso 1 1 calc R H14B H 0.3394 0.1031 0.3881 0.040 Uiso 1 1 calc R C15 C 0.04999(18) 0.14058(17) 0.41061(6) 0.0275(5) Uani 1 1 d . H15A H -0.0048 0.1744 0.3909 0.033 Uiso 1 1 calc R C16 C 0.15261(18) 0.06134(17) 0.39326(5) 0.0269(5) Uani 1 1 d . C17 C 0.0876(2) -0.00802(19) 0.36174(6) 0.0355(5) Uani 1 1 d . H17A H 0.1476 -0.0529 0.3462 0.043 Uiso 1 1 calc R H17B H 0.0389 0.0490 0.3462 0.043 Uiso 1 1 calc R C18 C 0.0027(2) -0.0986(2) 0.38301(6) 0.0374(5) Uani 1 1 d . H18A H -0.0854 -0.0803 0.3783 0.045 Uiso 1 1 calc R H18B H 0.0198 -0.1852 0.3759 0.045 Uiso 1 1 calc R C19 C 0.03585(19) -0.07573(18) 0.42362(6) 0.0316(5) Uani 1 1 d . H19A H 0.0154 -0.1459 0.4404 0.038 Uiso 1 1 calc R C20 C -0.02304(19) 0.04803(18) 0.43463(6) 0.0326(5) Uani 1 1 d . H20A H -0.0115 0.0651 0.4611 0.039 Uiso 1 1 calc R H20B H -0.1122 0.0497 0.4288 0.039 Uiso 1 1 calc R C21 C 0.17413(19) -0.04400(18) 0.42181(6) 0.0295(5) Uani 1 1 d . C22 C 0.2567(2) -0.14910(19) 0.40725(6) 0.0375(5) Uani 1 1 d . H22A H 0.2225 -0.1807 0.3842 0.056 Uiso 1 1 calc R H22B H 0.2597 -0.2159 0.4254 0.056 Uiso 1 1 calc R H22C H 0.3402 -0.1176 0.4029 0.056 Uiso 1 1 calc R C23 C 0.2302(2) -0.00409(19) 0.45871(6) 0.0359(5) Uani 1 1 d . H23A H 0.2248 -0.0725 0.4763 0.054 Uiso 1 1 calc R H23B H 0.1847 0.0671 0.4683 0.054 Uiso 1 1 calc R H23C H 0.3170 0.0185 0.4551 0.054 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 S1 0.0302(3) 0.0283(3) 0.0234(2) 0.0004(2) 0.0015(2) -0.0035(2) O1 0.0375(8) 0.0266(7) 0.0298(8) 0.0034(7) -0.0053(7) -0.0066(6) N1 0.0268(8) 0.0252(9) 0.0245(8) -0.0033(8) 0.0016(7) -0.0017(7) C1 0.0283(11) 0.0248(10) 0.0221(10) 0.0008(9) 0.0023(9) -0.0024(8) O2 0.0286(8) 0.0319(8) 0.0370(9) -0.0043(7) 0.0002(7) -0.0016(6) C2 0.0313(11) 0.0268(11) 0.0268(11) -0.0013(9) -0.0027(9) -0.0026(9) O3 0.0272(7) 0.0466(9) 0.0302(8) -0.0003(7) -0.0043(7) -0.0017(7) C3 0.0401(13) 0.0199(10) 0.0306(11) 0.0005(10) 0.0043(10) -0.0011(9) O4 0.0513(10) 0.0291(8) 0.0305(8) 0.0076(6) 0.0024(8) -0.0050(7) C4 0.0408(13) 0.0371(13) 0.0485(15) 0.0006(12) 0.0049(12) 0.0019(11) C5 0.0516(15) 0.0495(15) 0.0539(17) -0.0017(14) 0.0216(14) 0.0053(12) C6 0.077(2) 0.0456(15) 0.0316(13) -0.0030(12) 0.0160(15) 0.0043(13) C7 0.0621(16) 0.0351(13) 0.0283(12) -0.0036(11) 0.0003(12) -0.0012(11) C8 0.0448(13) 0.0247(11) 0.0295(11) -0.0015(10) 0.0002(11) 0.0003(9) C9 0.0402(12) 0.0280(11) 0.0258(11) 0.0000(10) -0.0057(10) -0.0022(9) C10 0.0303(11) 0.0292(11) 0.0233(10) -0.0007(9) 0.0006(9) 0.0008(9) C11 0.0418(13) 0.0341(12) 0.0391(13) 0.0032(11) -0.0120(11) -0.0015(10) C12 0.0432(14) 0.0419(14) 0.0423(13) -0.0024(12) -0.0113(12) -0.0061(10) C13 0.0319(12) 0.0271(10) 0.0211(10) 0.0008(9) -0.0006(9) -0.0016(9) C14 0.0373(12) 0.0340(11) 0.0284(11) -0.0009(9) 0.0076(10) 0.0000(10) C15 0.0305(11) 0.0235(10) 0.0286(11) -0.0038(9) -0.0030(10) -0.0028(8) C16 0.0312(11) 0.0267(11) 0.0228(10) -0.0029(9) 0.0024(9) -0.0023(9) C17 0.0432(13) 0.0334(12) 0.0299(12) -0.0063(10) -0.0036(11) 0.0002(10) C18 0.0396(13) 0.0308(12) 0.0418(13) -0.0095(11) -0.0031(11) -0.0037(10) C19 0.0359(12) 0.0224(10) 0.0364(12) -0.0002(10) 0.0054(10) -0.0044(9) C20 0.0296(11) 0.0304(11) 0.0380(13) -0.0038(10) 0.0042(10) -0.0041(9) C21 0.0322(11) 0.0273(11) 0.0290(11) -0.0002(9) 0.0023(10) 0.0008(9) C22 0.0414(13) 0.0309(11) 0.0403(13) 0.0029(10) 0.0039(11) 0.0045(10) C23 0.0425(13) 0.0359(12) 0.0294(12) 0.0063(10) -0.0027(11) 0.0002(10) 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' N N 0.0061 0.0033 '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 O4 S1 O3 117.66(9) O4 S1 N1 109.45(8) O3 S1 N1 110.22(8) O4 S1 C14 110.65(9) O3 S1 C14 110.84(10) N1 S1 C14 95.84(9) C2 O1 C9 97.39(14) C13 N1 C15 115.42(15) C13 N1 S1 121.90(13) C15 N1 S1 111.32(12) C10 C1 C13 131.01(19) C10 C1 C2 106.20(16) C13 C1 C2 121.80(16) O1 C2 C11 113.33(16) O1 C2 C3 98.79(15) C11 C2 C3 118.65(18) O1 C2 C1 98.48(14) C11 C2 C1 118.29(16) C3 C2 C1 105.83(16) C4 C3 C8 121.4(2) C4 C3 C2 133.5(2) C8 C3 C2 105.07(18) C3 C4 C5 117.2(2) C6 C5 C4 121.6(2) C5 C6 C7 120.8(2) C8 C7 C6 117.7(2) C7 C8 C3 121.3(2) C7 C8 C9 133.9(2) C3 C8 C9 104.79(17) O1 C9 C12 112.92(17) O1 C9 C8 99.06(15) C12 C9 C8 119.12(17) O1 C9 C10 99.54(15) C12 C9 C10 117.58(17) C8 C9 C10 105.41(16) C1 C10 C9 106.16(17) O2 C13 N1 119.56(17) O2 C13 C1 121.71(18) N1 C13 C1 118.71(17) C16 C14 S1 107.63(14) N1 C15 C16 107.81(15) N1 C15 C20 115.52(16) C16 C15 C20 103.86(15) C14 C16 C15 108.21(15) C14 C16 C17 117.99(17) C15 C16 C17 104.29(17) C14 C16 C21 118.68(17) C15 C16 C21 104.02(15) C17 C16 C21 101.97(15) C16 C17 C18 101.99(16) C19 C18 C17 103.79(16) C20 C19 C21 102.73(15) C20 C19 C18 107.08(17) C21 C19 C18 102.83(17) C19 C20 C15 101.85(15) C23 C21 C19 114.26(17) C23 C21 C22 106.19(17) C19 C21 C22 114.48(17) C23 C21 C16 115.81(16) C19 C21 C16 92.66(15) C22 C21 C16 113.44(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O4 1.4271(14) S1 O3 1.4318(14) S1 N1 1.7023(16) S1 C14 1.787(2) O1 C2 1.452(2) O1 C9 1.458(2) N1 C13 1.396(2) N1 C15 1.479(2) C1 C10 1.324(3) C1 C13 1.463(3) C1 C2 1.552(3) O2 C13 1.222(2) C2 C11 1.495(3) C2 C3 1.535(3) C3 C4 1.377(3) C3 C8 1.397(3) C4 C5 1.399(3) C5 C6 1.374(3) C6 C7 1.402(3) C7 C8 1.372(3) C8 C9 1.529(3) C9 C12 1.500(3) C9 C10 1.538(3) C14 C16 1.521(3) C15 C16 1.540(3) C15 C20 1.548(3) C16 C17 1.542(3) C16 C21 1.561(3) C17 C18 1.552(3) C18 C19 1.541(3) C19 C20 1.538(3) C19 C21 1.538(3) C21 C23 1.536(3) C21 C22 1.542(3)