#------------------------------------------------------------------------------ #$Date: 2016-03-26 14:58:14 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180282 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/68/7116896.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_7116896 loop_ _publ_author_name 'Hai-Bin Yang' 'Yu-Chao Yuan' 'Yin Wei' 'Min Shi' _publ_section_title ; Amine-catalyzed tunable reactions of allenoates with dithioesters: formal [4+2] and [2+2] cycloadditions for the synthesis of 2,3-dihydro-1,4-oxathiines and enantioenriched thietanes ; _journal_name_full Chem.Commun. _journal_page_first 6430 _journal_paper_doi 10.1039/C5cc01313E _journal_volume 51 _journal_year 2015 _chemical_formula_sum 'C22 H27 N O4 S' _chemical_formula_weight 401.50 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2013 _audit_update_record ; 2014-10-17 deposited with the CCDC. 2015-03-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.427(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 31.687(3) _cell_length_b 6.2286(5) _cell_length_c 23.0782(19) _cell_measurement_reflns_used 1840 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 55.486 _cell_measurement_theta_min 5.129 _cell_volume 4368.9(7) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_unetI/netI 0.0500 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 12101 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.499 _diffrn_reflns_theta_min 1.840 _exptl_absorpt_coefficient_mu 0.174 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6831 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.221 _exptl_crystal_description prismatic _exptl_crystal_F_000 1712 _exptl_crystal_size_max 0.156 _exptl_crystal_size_mid 0.123 _exptl_crystal_size_min 0.086 _refine_diff_density_max 0.236 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.050 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 261 _refine_ls_number_reflns 4064 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.110 _refine_ls_R_factor_all 0.1071 _refine_ls_R_factor_gt 0.0693 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0766P)^2^+0.8909P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1556 _refine_ls_wR_factor_ref 0.1746 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2630 _reflns_number_total 4064 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c5cc01313e2.cif _cod_data_source_block cd214587 _cod_original_cell_volume 4368.9(6) _cod_database_code 7116896 #BEGIN Tags that were not found in dictionaries: _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2013-4 _shelx_res_file ; TITL cd214587 in C2/c CELL 0.71073 31.6869 6.2286 23.0782 90.000 106.427 90.000 ZERR 8.00 0.0026 0.0005 0.0019 0.000 0.003 0.000 LATT 7 SYMM -X, Y, 0.5-Z SFAC C H N O S UNIT 176 216 8 32 8 omit -2 0 2 OMIT -3.00 51.00 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 conf htab mpla c12 > c17 mpla c4 > c9 wpdb -1 WGHT 0.076600 0.890900 FVAR 0.07797 MOLE 1 S1 5 0.187013 0.358725 1.038030 11.00000 0.07215 0.05181 = 0.06889 0.01583 -0.00899 -0.00845 AFIX 83 H1A 2 0.168186 0.350012 1.076363 11.00000 -1.50000 AFIX 0 N1 3 0.105748 0.965773 1.047518 11.00000 0.08208 0.05565 = 0.06590 0.00737 0.03817 -0.00401 O1 4 0.106329 0.609993 1.058180 11.00000 0.10869 0.06751 = 0.09322 0.01816 0.05355 -0.01829 O2 4 0.259529 0.483338 0.812325 11.00000 0.08743 0.15393 = 0.09778 -0.02822 0.04588 -0.00240 O3 4 0.099951 0.266116 0.947645 11.00000 0.06372 0.04606 = 0.08202 0.01176 -0.00332 -0.01557 O4 4 0.086568 0.604651 0.914700 11.00000 0.04538 0.04677 = 0.05866 0.00930 0.01107 -0.00202 C1 1 0.119563 0.770300 1.038831 11.00000 0.06276 0.05543 = 0.04303 0.00602 0.01463 -0.01099 C2 1 0.152456 0.762593 1.002249 11.00000 0.05470 0.04302 = 0.04766 0.00312 0.01161 -0.01146 AFIX 23 H2A 2 0.180948 0.808836 1.027553 11.00000 -1.20000 H2B 2 0.143330 0.862753 0.968849 11.00000 -1.20000 AFIX 0 C3 1 0.157099 0.539236 0.977290 11.00000 0.04921 0.03901 = 0.04887 0.00568 0.00507 -0.00555 C4 1 0.183434 0.538857 0.931459 11.00000 0.04261 0.04525 = 0.05434 0.00031 0.00232 -0.00194 C5 1 0.183464 0.356068 0.896794 11.00000 0.06845 0.05690 = 0.07787 -0.01074 0.01822 -0.00761 AFIX 43 H5 2 0.165872 0.239922 0.900187 11.00000 -1.20000 AFIX 0 C6 1 0.208776 0.343896 0.857952 11.00000 0.08171 0.07661 = 0.08519 -0.02543 0.02400 0.00042 AFIX 43 H6 2 0.208493 0.219132 0.835708 11.00000 -1.20000 AFIX 0 C7 1 0.234914 0.515074 0.851206 11.00000 0.05386 0.09711 = 0.06282 -0.00840 0.01556 0.00496 C8 1 0.235010 0.696168 0.884261 11.00000 0.05058 0.07580 = 0.06364 0.00119 0.01318 -0.00714 AFIX 43 H8 2 0.252143 0.812964 0.879906 11.00000 -1.20000 AFIX 0 C9 1 0.209832 0.707682 0.924237 11.00000 0.05088 0.05578 = 0.05978 -0.00449 0.01045 -0.00669 AFIX 43 H9 2 0.210659 0.832024 0.946842 11.00000 -1.20000 AFIX 0 C10 1 0.289414 0.645192 0.807665 11.00000 0.08368 0.17827 = 0.09709 0.00953 0.04763 0.00233 AFIX 137 H10A 2 0.273459 0.771027 0.789831 11.00000 -1.50000 H10B 2 0.307106 0.595386 0.782806 11.00000 -1.50000 H10C 2 0.308053 0.679525 0.847182 11.00000 -1.50000 AFIX 0 C11 1 0.073198 1.006233 1.079396 11.00000 0.06494 0.09618 = 0.06707 0.00393 0.02671 0.00753 AFIX 23 H11A 2 0.053789 0.882939 1.074305 11.00000 -1.20000 H11B 2 0.055538 1.128624 1.060938 11.00000 -1.20000 AFIX 0 C12 1 0.091870 1.049465 1.145758 11.00000 0.05007 0.06381 = 0.06357 0.00694 0.02547 0.00470 C13 1 0.110105 1.244555 1.165805 11.00000 0.10694 0.06576 = 0.08496 0.01289 0.03928 -0.00246 AFIX 43 H13 2 0.111089 1.350660 1.137865 11.00000 -1.20000 AFIX 0 C14 1 0.126985 1.286697 1.226412 11.00000 0.12735 0.08234 = 0.09718 -0.01972 0.03171 -0.01287 AFIX 43 H14 2 0.139696 1.419492 1.239038 11.00000 -1.20000 AFIX 0 C15 1 0.125193 1.136982 1.267422 11.00000 0.08932 0.13562 = 0.06555 -0.00987 0.02389 0.00416 AFIX 43 H15 2 0.136429 1.165826 1.308450 11.00000 -1.20000 AFIX 0 C16 1 0.106878 0.943254 1.248618 11.00000 0.08881 0.12751 = 0.07275 0.03498 0.03313 0.00196 AFIX 43 H16 2 0.105512 0.839227 1.276939 11.00000 -1.20000 AFIX 0 C17 1 0.090220 0.899095 1.187703 11.00000 0.07166 0.07769 = 0.07898 0.01440 0.02780 -0.00987 AFIX 43 H17 2 0.077798 0.765524 1.175350 11.00000 -1.20000 AFIX 0 C18 1 0.111212 0.448579 0.945894 11.00000 0.05237 0.04377 = 0.04943 0.00267 0.01186 -0.00605 C19 1 0.039729 0.572003 0.881452 11.00000 0.04510 0.06699 = 0.05896 0.00388 0.00909 -0.00347 C20 1 0.026058 0.794743 0.857404 11.00000 0.05671 0.08451 = 0.11974 0.02668 0.01017 0.01832 AFIX 137 H20A 2 0.029256 0.892270 0.890580 11.00000 -1.50000 H20B 2 -0.004110 0.792414 0.833385 11.00000 -1.50000 H20C 2 0.044347 0.841020 0.832973 11.00000 -1.50000 AFIX 0 C21 1 0.015194 0.500367 0.925591 11.00000 0.05765 0.12007 = 0.09081 0.00917 0.02731 -0.01150 AFIX 137 H21A 2 0.024286 0.357764 0.939404 11.00000 -1.50000 H21B 2 -0.015859 0.501228 0.905933 11.00000 -1.50000 H21C 2 0.021588 0.596655 0.959445 11.00000 -1.50000 AFIX 0 C22 1 0.036309 0.416012 0.831553 11.00000 0.07858 0.10462 = 0.06645 -0.01007 -0.00267 -0.00207 AFIX 137 H22A 2 0.053301 0.466584 0.805851 11.00000 -1.50000 H22B 2 0.006066 0.401745 0.808445 11.00000 -1.50000 H22C 2 0.047353 0.279003 0.848149 11.00000 -1.50000 AFIX 0 H1 2 0.115141 1.065269 1.029822 11.00000 0.04465 HKLF 4 REM cd214587 in C2/c REM R1 = 0.0693 for 2630 Fo > 4sig(Fo) and 0.1071 for all 4064 data REM 261 parameters refined using 0 restraints END WGHT 0.0766 0.8909 REM Instructions for potential hydrogen bonds HTAB S1 O1 EQIV $1 -x+1/2, y+1/2, -z+3/2 HTAB C10 O2_$1 HTAB C21 O3 HTAB C22 O3 EQIV $2 x, y+1, z HTAB N1 S1_$2 HTAB N1 O3_$2 REM Highest difference peak 0.236, deepest hole -0.205, 1-sigma level 0.050 Q1 1 0.1608 0.4353 1.0110 11.00000 0.05 0.24 Q2 1 0.2082 0.3790 1.0792 11.00000 0.05 0.22 Q3 1 0.0964 0.7004 1.0372 11.00000 0.05 0.21 Q4 1 0.2186 0.3657 1.0340 11.00000 0.05 0.20 Q5 1 0.1049 1.2504 1.1978 11.00000 0.05 0.20 Q6 1 0.2080 0.5144 1.0597 11.00000 0.05 0.20 Q7 1 0.0816 1.1074 1.1687 11.00000 0.05 0.20 Q8 1 0.2054 0.4838 0.8325 11.00000 0.05 0.19 Q9 1 0.0864 1.1381 1.1611 11.00000 0.05 0.19 Q10 1 0.1014 1.1266 1.1441 11.00000 0.05 0.19 Q11 1 0.1707 0.2215 1.0272 11.00000 0.05 0.18 Q12 1 0.1907 0.4844 1.0157 11.00000 0.05 0.18 Q13 1 0.2036 0.3254 1.0029 11.00000 0.05 0.18 Q14 1 0.1341 0.4908 0.9718 11.00000 0.05 0.18 Q15 1 0.1010 0.7222 0.9207 11.00000 0.05 0.17 Q16 1 0.0580 0.6153 0.8892 11.00000 0.05 0.17 Q17 1 0.1008 0.3487 0.9406 11.00000 0.05 0.17 Q18 1 0.1245 0.7479 1.0784 11.00000 0.05 0.17 Q19 1 0.0959 0.5577 0.9454 11.00000 0.05 0.17 Q20 1 0.1836 0.6488 0.9170 11.00000 0.05 0.17 ; _shelx_res_checksum 5550 #END Tags that were not found in dictionaries loop_ _space_group_symop_operation_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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.18701(3) 0.35873(14) 1.03803(4) 0.0702(3) Uani 1 1 d . . . . . H1A H 0.1682 0.3500 1.0764 0.105 Uiso 1 1 calc R U . . . N1 N 0.10575(10) 0.9658(5) 1.04752(13) 0.0643(8) Uani 1 1 d . . . . . O1 O 0.10633(9) 0.6100(4) 1.05818(11) 0.0847(8) Uani 1 1 d . . . . . O2 O 0.25953(10) 0.4833(6) 0.81233(13) 0.1090(10) Uani 1 1 d . . . . . O3 O 0.09995(7) 0.2661(3) 0.94764(10) 0.0688(7) Uani 1 1 d . . . . . O4 O 0.08657(6) 0.6047(3) 0.91470(9) 0.0510(5) Uani 1 1 d . . . . . C1 C 0.11956(10) 0.7703(5) 1.03883(13) 0.0538(8) Uani 1 1 d . . . . . C2 C 0.15246(9) 0.7626(5) 1.00225(12) 0.0490(7) Uani 1 1 d . . . . . H2A H 0.1809 0.8088 1.0276 0.059 Uiso 1 1 calc R U . . . H2B H 0.1433 0.8628 0.9688 0.059 Uiso 1 1 calc R U . . . C3 C 0.15710(9) 0.5392(4) 0.97729(12) 0.0475(7) Uani 1 1 d . . . . . C4 C 0.18343(9) 0.5389(5) 0.93146(13) 0.0497(7) Uani 1 1 d . . . . . C5 C 0.18346(11) 0.3561(5) 0.89679(16) 0.0682(9) Uani 1 1 d . . . . . H5 H 0.1659 0.2399 0.9002 0.082 Uiso 1 1 calc R U . . . C6 C 0.20878(13) 0.3439(6) 0.85795(18) 0.0811(11) Uani 1 1 d . . . . . H6 H 0.2085 0.2191 0.8357 0.097 Uiso 1 1 calc R U . . . C7 C 0.23491(11) 0.5151(7) 0.85121(16) 0.0715(10) Uani 1 1 d . . . . . C8 C 0.23501(10) 0.6962(6) 0.88426(15) 0.0640(9) Uani 1 1 d . . . . . H8 H 0.2521 0.8130 0.8799 0.077 Uiso 1 1 calc R U . . . C9 C 0.20983(10) 0.7077(5) 0.92424(14) 0.0565(8) Uani 1 1 d . . . . . H9 H 0.2107 0.8320 0.9468 0.068 Uiso 1 1 calc R U . . . C10 C 0.28941(15) 0.6452(9) 0.8077(2) 0.1152(17) Uani 1 1 d . . . . . H10A H 0.2735 0.7710 0.7898 0.173 Uiso 1 1 calc R U . . . H10B H 0.3071 0.5954 0.7828 0.173 Uiso 1 1 calc R U . . . H10C H 0.3081 0.6795 0.8472 0.173 Uiso 1 1 calc R U . . . C11 C 0.07320(11) 1.0062(6) 1.07940(15) 0.0744(10) Uani 1 1 d . . . . . H11A H 0.0538 0.8829 1.0743 0.089 Uiso 1 1 calc R U . . . H11B H 0.0555 1.1286 1.0609 0.089 Uiso 1 1 calc R U . . . C12 C 0.09187(10) 1.0495(5) 1.14576(14) 0.0572(8) Uani 1 1 d . . . . . C13 C 0.11010(14) 1.2446(6) 1.16581(19) 0.0834(11) Uani 1 1 d . . . . . H13 H 0.1111 1.3507 1.1379 0.100 Uiso 1 1 calc R U . . . C14 C 0.12699(16) 1.2867(8) 1.2264(2) 0.1023(14) Uani 1 1 d . . . . . H14 H 0.1397 1.4195 1.2390 0.123 Uiso 1 1 calc R U . . . C15 C 0.12519(15) 1.1370(9) 1.26742(19) 0.0964(14) Uani 1 1 d . . . . . H15 H 0.1364 1.1658 1.3085 0.116 Uiso 1 1 calc R U . . . C16 C 0.10688(14) 0.9433(9) 1.24862(19) 0.0942(13) Uani 1 1 d . . . . . H16 H 0.1055 0.8392 1.2769 0.113 Uiso 1 1 calc R U . . . C17 C 0.09022(12) 0.8991(6) 1.18770(17) 0.0748(10) Uani 1 1 d . . . . . H17 H 0.0778 0.7655 1.1753 0.090 Uiso 1 1 calc R U . . . C18 C 0.11121(10) 0.4486(5) 0.94589(13) 0.0490(7) Uani 1 1 d . . . . . C19 C 0.03973(10) 0.5720(5) 0.88145(14) 0.0582(8) Uani 1 1 d . . . . . C20 C 0.02606(12) 0.7947(6) 0.8574(2) 0.0900(13) Uani 1 1 d . . . . . H20A H 0.0293 0.8923 0.8906 0.135 Uiso 1 1 calc R U . . . H20B H -0.0041 0.7924 0.8334 0.135 Uiso 1 1 calc R U . . . H20C H 0.0443 0.8410 0.8330 0.135 Uiso 1 1 calc R U . . . C21 C 0.01519(12) 0.5004(7) 0.92559(18) 0.0882(12) Uani 1 1 d . . . . . H21A H 0.0243 0.3578 0.9394 0.132 Uiso 1 1 calc R U . . . H21B H -0.0159 0.5012 0.9059 0.132 Uiso 1 1 calc R U . . . H21C H 0.0216 0.5967 0.9594 0.132 Uiso 1 1 calc R U . . . C22 C 0.03631(13) 0.4160(7) 0.83155(16) 0.0880(12) Uani 1 1 d . . . . . H22A H 0.0533 0.4666 0.8059 0.132 Uiso 1 1 calc R U . . . H22B H 0.0061 0.4017 0.8084 0.132 Uiso 1 1 calc R U . . . H22C H 0.0474 0.2790 0.8481 0.132 Uiso 1 1 calc R U . . . H1 H 0.1151(9) 1.065(5) 1.0298(12) 0.045(8) 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 S1 0.0722(6) 0.0518(5) 0.0689(6) 0.0158(4) -0.0090(4) -0.0085(4) N1 0.082(2) 0.0557(18) 0.0659(18) 0.0074(15) 0.0382(16) -0.0040(16) O1 0.109(2) 0.0675(16) 0.0932(18) 0.0182(14) 0.0535(16) -0.0183(14) O2 0.087(2) 0.154(3) 0.098(2) -0.028(2) 0.0459(17) -0.002(2) O3 0.0637(14) 0.0461(13) 0.0820(15) 0.0118(12) -0.0033(11) -0.0156(11) O4 0.0454(11) 0.0468(12) 0.0587(12) 0.0093(10) 0.0111(9) -0.0020(9) C1 0.0628(19) 0.055(2) 0.0430(15) 0.0060(15) 0.0146(14) -0.0110(16) C2 0.0547(17) 0.0430(16) 0.0477(16) 0.0031(13) 0.0116(14) -0.0115(14) C3 0.0492(16) 0.0390(16) 0.0489(16) 0.0057(13) 0.0051(13) -0.0055(13) C4 0.0426(16) 0.0452(17) 0.0543(17) 0.0003(14) 0.0023(13) -0.0019(14) C5 0.068(2) 0.057(2) 0.078(2) -0.0107(18) 0.0182(19) -0.0076(17) C6 0.082(3) 0.077(3) 0.085(3) -0.025(2) 0.024(2) 0.000(2) C7 0.054(2) 0.097(3) 0.063(2) -0.008(2) 0.0156(17) 0.005(2) C8 0.0506(18) 0.076(2) 0.064(2) 0.0012(18) 0.0132(16) -0.0071(17) C9 0.0509(17) 0.0558(19) 0.0598(18) -0.0045(15) 0.0105(15) -0.0067(15) C10 0.084(3) 0.178(5) 0.097(3) 0.010(3) 0.048(3) 0.002(3) C11 0.065(2) 0.096(3) 0.067(2) 0.004(2) 0.0267(18) 0.008(2) C12 0.0501(17) 0.064(2) 0.064(2) 0.0069(17) 0.0255(15) 0.0047(16) C13 0.107(3) 0.066(2) 0.085(3) 0.013(2) 0.039(2) -0.002(2) C14 0.127(4) 0.082(3) 0.097(3) -0.020(3) 0.032(3) -0.013(3) C15 0.089(3) 0.136(4) 0.066(3) -0.010(3) 0.024(2) 0.004(3) C16 0.089(3) 0.128(4) 0.073(3) 0.035(3) 0.033(2) 0.002(3) C17 0.072(2) 0.078(3) 0.079(3) 0.014(2) 0.028(2) -0.0099(19) C18 0.0524(17) 0.0438(17) 0.0494(16) 0.0027(14) 0.0119(14) -0.0060(15) C19 0.0451(17) 0.067(2) 0.0590(19) 0.0039(16) 0.0091(14) -0.0035(15) C20 0.057(2) 0.085(3) 0.120(3) 0.027(2) 0.010(2) 0.018(2) C21 0.058(2) 0.120(4) 0.091(3) 0.009(3) 0.027(2) -0.012(2) C22 0.079(3) 0.105(3) 0.066(2) -0.010(2) -0.0027(19) -0.002(2) 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' N N 0.0061 0.0033 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C3 S1 H1A 109.5 . . C1 N1 C11 123.3(3) . . C1 N1 H1 115(2) . . C11 N1 H1 121(2) . . C7 O2 C10 118.0(4) . . C18 O4 C19 122.1(2) . . O1 C1 N1 122.3(3) . . O1 C1 C2 122.8(3) . . N1 C1 C2 114.9(3) . . C1 C2 C3 113.2(2) . . C1 C2 H2A 108.9 . . C3 C2 H2A 108.9 . . C1 C2 H2B 108.9 . . C3 C2 H2B 108.9 . . H2A C2 H2B 107.8 . . C4 C3 C2 113.2(2) . . C4 C3 C18 107.7(2) . . C2 C3 C18 109.4(2) . . C4 C3 S1 105.27(19) . . C2 C3 S1 110.69(19) . . C18 C3 S1 110.49(19) . . C9 C4 C5 117.0(3) . . C9 C4 C3 123.5(3) . . C5 C4 C3 119.4(3) . . C6 C5 C4 121.3(3) . . C6 C5 H5 119.3 . . C4 C5 H5 119.3 . . C5 C6 C7 120.8(4) . . C5 C6 H6 119.6 . . C7 C6 H6 119.6 . . O2 C7 C8 125.4(4) . . O2 C7 C6 115.8(4) . . C8 C7 C6 118.8(3) . . C7 C8 C9 120.5(3) . . C7 C8 H8 119.8 . . C9 C8 H8 119.8 . . C8 C9 C4 121.6(3) . . C8 C9 H9 119.2 . . C4 C9 H9 119.2 . . O2 C10 H10A 109.5 . . O2 C10 H10B 109.5 . . H10A C10 H10B 109.5 . . O2 C10 H10C 109.5 . . H10A C10 H10C 109.5 . . H10B C10 H10C 109.5 . . N1 C11 C12 114.7(3) . . N1 C11 H11A 108.6 . . C12 C11 H11A 108.6 . . N1 C11 H11B 108.6 . . C12 C11 H11B 108.6 . . H11A C11 H11B 107.6 . . C17 C12 C13 118.0(3) . . C17 C12 C11 121.3(3) . . C13 C12 C11 120.7(3) . . C12 C13 C14 121.3(4) . . C12 C13 H13 119.4 . . C14 C13 H13 119.4 . . C15 C14 C13 120.2(4) . . C15 C14 H14 119.9 . . C13 C14 H14 119.9 . . C14 C15 C16 119.5(4) . . C14 C15 H15 120.2 . . C16 C15 H15 120.2 . . C15 C16 C17 120.6(4) . . C15 C16 H16 119.7 . . C17 C16 H16 119.7 . . C12 C17 C16 120.5(4) . . C12 C17 H17 119.8 . . C16 C17 H17 119.8 . . O3 C18 O4 125.5(3) . . O3 C18 C3 125.8(3) . . O4 C18 C3 108.7(2) . . O4 C19 C22 109.5(3) . . O4 C19 C20 101.9(2) . . C22 C19 C20 111.4(3) . . O4 C19 C21 108.8(2) . . C22 C19 C21 112.9(3) . . C20 C19 C21 111.7(3) . . C19 C20 H20A 109.5 . . C19 C20 H20B 109.5 . . H20A C20 H20B 109.5 . . C19 C20 H20C 109.5 . . H20A C20 H20C 109.5 . . H20B C20 H20C 109.5 . . C19 C21 H21A 109.5 . . C19 C21 H21B 109.5 . . H21A C21 H21B 109.5 . . C19 C21 H21C 109.5 . . H21A C21 H21C 109.5 . . H21B C21 H21C 109.5 . . C19 C22 H22A 109.5 . . C19 C22 H22B 109.5 . . H22A C22 H22B 109.5 . . C19 C22 H22C 109.5 . . H22A C22 H22C 109.5 . . H22B C22 H22C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 C3 1.837(3) . S1 H1A 1.2000 . N1 C1 1.328(4) . N1 C11 1.448(4) . N1 H1 0.84(3) . O1 C1 1.216(3) . O2 C7 1.360(4) . O2 C10 1.408(5) . O3 C18 1.195(3) . O4 C18 1.325(3) . O4 C19 1.479(3) . C1 C2 1.516(4) . C2 C3 1.529(4) . C2 H2A 0.9700 . C2 H2B 0.9700 . C3 C4 1.521(4) . C3 C18 1.537(4) . C4 C9 1.383(4) . C4 C5 1.392(4) . C5 C6 1.364(5) . C5 H5 0.9300 . C6 C7 1.386(5) . C6 H6 0.9300 . C7 C8 1.361(5) . C8 C9 1.382(4) . C8 H8 0.9300 . C9 H9 0.9300 . C10 H10A 0.9600 . C10 H10B 0.9600 . C10 H10C 0.9600 . C11 C12 1.502(5) . C11 H11A 0.9700 . C11 H11B 0.9700 . C12 C17 1.359(4) . C12 C13 1.369(5) . C13 C14 1.374(6) . C13 H13 0.9300 . C14 C15 1.341(6) . C14 H14 0.9300 . C15 C16 1.356(6) . C15 H15 0.9300 . C16 C17 1.382(5) . C16 H16 0.9300 . C17 H17 0.9300 . C19 C22 1.487(5) . C19 C20 1.511(5) . C19 C21 1.513(5) . C20 H20A 0.9600 . C20 H20B 0.9600 . C20 H20C 0.9600 . C21 H21A 0.9600 . C21 H21B 0.9600 . C21 H21C 0.9600 . C22 H22A 0.9600 . C22 H22B 0.9600 . C22 H22C 0.9600 . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C11 N1 C1 O1 -1.4(5) . . . . C11 N1 C1 C2 177.7(3) . . . . O1 C1 C2 C3 16.3(4) . . . . N1 C1 C2 C3 -162.8(3) . . . . C1 C2 C3 C4 169.5(2) . . . . C1 C2 C3 C18 49.4(3) . . . . C1 C2 C3 S1 -72.6(3) . . . . C2 C3 C4 C9 15.7(4) . . . . C18 C3 C4 C9 136.8(3) . . . . S1 C3 C4 C9 -105.3(3) . . . . C2 C3 C4 C5 -168.1(3) . . . . C18 C3 C4 C5 -47.0(3) . . . . S1 C3 C4 C5 70.9(3) . . . . C9 C4 C5 C6 0.6(5) . . . . C3 C4 C5 C6 -175.8(3) . . . . C4 C5 C6 C7 -0.9(6) . . . . C10 O2 C7 C8 3.5(5) . . . . C10 O2 C7 C6 -174.7(4) . . . . C5 C6 C7 O2 178.5(3) . . . . C5 C6 C7 C8 0.2(6) . . . . O2 C7 C8 C9 -177.5(3) . . . . C6 C7 C8 C9 0.7(5) . . . . C7 C8 C9 C4 -0.9(5) . . . . C5 C4 C9 C8 0.2(4) . . . . C3 C4 C9 C8 176.5(3) . . . . C1 N1 C11 C12 92.8(4) . . . . N1 C11 C12 C17 -105.0(4) . . . . N1 C11 C12 C13 76.7(4) . . . . C17 C12 C13 C14 1.1(6) . . . . C11 C12 C13 C14 179.5(4) . . . . C12 C13 C14 C15 -1.1(7) . . . . C13 C14 C15 C16 0.5(7) . . . . C14 C15 C16 C17 0.2(7) . . . . C13 C12 C17 C16 -0.5(5) . . . . C11 C12 C17 C16 -178.8(3) . . . . C15 C16 C17 C12 -0.1(6) . . . . C19 O4 C18 O3 5.1(4) . . . . C19 O4 C18 C3 -177.1(2) . . . . C4 C3 C18 O3 95.4(3) . . . . C2 C3 C18 O3 -141.2(3) . . . . S1 C3 C18 O3 -19.1(4) . . . . C4 C3 C18 O4 -82.4(3) . . . . C2 C3 C18 O4 41.0(3) . . . . S1 C3 C18 O4 163.11(19) . . . . C18 O4 C19 C22 -65.3(3) . . . . C18 O4 C19 C20 176.7(3) . . . . C18 O4 C19 C21 58.6(4) . . . .