# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Chen Zhu' _publ_contact_author_email chen.zhu@utsouthwestern.edu _publ_section_title ; Rhodium Catalyzed C-H Olefination of N-Benzoylsulfonamide with Internal Alkenes ; loop_ _publ_author_name 'Chen Zhu' J.Falck # Attachment '- X-ray structure of compound 6a.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 843998' #TrackingRef '- X-ray structure of compound 6a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H23 N O7 S' _chemical_formula_sum 'C22 H23 N O7 S' _chemical_formula_weight 445.47 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.754(2) _cell_length_b 8.5111(12) _cell_length_c 17.209(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.714(4) _cell_angle_gamma 90.00 _cell_volume 2069.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 37907 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prisms _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.890 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC-12 with Saturn 724+ CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36400 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 27.35 _reflns_number_total 4640 _reflns_number_gt 4280 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-ray Diffraction Data. Sheldrick, G. M. (2008). SHELXL-97. Acta Cryst., A64, 112-122. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_acknowledgements ; The data were collected using instrumentation purchased with funds provided by the National Science Foundation Grant No. 0741973. ; _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0266P)^2^+1.7790P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4640 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.0883 _refine_ls_wR_factor_gt 0.0868 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.68954(3) 0.19526(4) 0.44719(2) 0.01497(9) Uani 1 1 d . . . N1 N 0.76617(9) 0.33954(15) 0.48628(7) 0.0146(3) Uani 1 1 d . . . O1 O 0.89119(8) 0.19081(14) 0.56857(7) 0.0212(2) Uani 1 1 d . . . O2 O 0.74203(8) 0.06943(14) 0.42528(7) 0.0210(2) Uani 1 1 d . . . O3 O 0.61477(8) 0.27240(14) 0.38646(6) 0.0191(2) Uani 1 1 d . . . O4 O 0.66401(8) 0.65895(13) 0.34986(6) 0.0195(2) Uani 1 1 d . . . O5 O 0.75945(7) 0.45717(13) 0.33764(6) 0.0173(2) Uani 1 1 d . . . O6 O 0.74630(8) 0.47726(16) 0.64066(7) 0.0240(3) Uani 1 1 d . . . O7 O 0.60086(8) 0.58663(15) 0.61524(6) 0.0214(3) Uani 1 1 d . . . C1 C 0.74155(10) 0.50739(18) 0.46974(9) 0.0141(3) Uani 1 1 d . . . C2 C 0.83615(10) 0.58621(19) 0.51185(8) 0.0146(3) Uani 1 1 d . . . C3 C 0.85875(11) 0.74486(19) 0.51317(9) 0.0176(3) Uani 1 1 d . . . H3 H 0.8134 0.8204 0.4856 0.021 Uiso 1 1 calc R . . C4 C 0.95096(11) 0.7895(2) 0.55673(9) 0.0198(3) Uani 1 1 d . . . H4 H 0.9684 0.8972 0.5588 0.024 Uiso 1 1 calc R . . C5 C 1.01781(11) 0.6778(2) 0.59730(9) 0.0198(3) Uani 1 1 d . . . H5 H 1.0798 0.7107 0.6263 0.024 Uiso 1 1 calc R . . C6 C 0.99418(10) 0.5187(2) 0.59545(9) 0.0175(3) Uani 1 1 d . . . H6 H 1.0391 0.4425 0.6228 0.021 Uiso 1 1 calc R . . C7 C 0.90226(10) 0.47520(18) 0.55201(9) 0.0150(3) Uani 1 1 d . . . C8 C 0.85891(10) 0.31653(19) 0.54021(9) 0.0156(3) Uani 1 1 d . . . C9 C 0.64421(11) 0.13304(18) 0.52641(9) 0.0152(3) Uani 1 1 d . . . C10 C 0.55452(11) 0.18575(19) 0.52697(9) 0.0176(3) Uani 1 1 d . . . H10 H 0.5182 0.2514 0.4848 0.021 Uiso 1 1 calc R . . C11 C 0.51973(11) 0.14022(19) 0.59040(9) 0.0184(3) Uani 1 1 d . . . H11 H 0.4587 0.1745 0.5911 0.022 Uiso 1 1 calc R . . C12 C 0.57287(11) 0.04467(19) 0.65342(9) 0.0173(3) Uani 1 1 d . . . C13 C 0.66144(11) -0.00961(19) 0.65028(9) 0.0177(3) Uani 1 1 d . . . H13 H 0.6973 -0.0768 0.6919 0.021 Uiso 1 1 calc R . . C14 C 0.69780(11) 0.03353(18) 0.58700(9) 0.0171(3) Uani 1 1 d . . . H14 H 0.7578 -0.0039 0.5851 0.020 Uiso 1 1 calc R . . C15 C 0.53548(12) 0.0070(2) 0.72443(10) 0.0224(3) Uani 1 1 d . . . H15A H 0.5152 0.1042 0.7450 0.034 Uiso 1 1 calc R . . H15B H 0.5855 -0.0429 0.7676 0.034 Uiso 1 1 calc R . . H15C H 0.4815 -0.0648 0.7067 0.034 Uiso 1 1 calc R . . C16 C 0.66082(10) 0.56421(19) 0.50368(9) 0.0158(3) Uani 1 1 d . . . H16A H 0.6520 0.6785 0.4935 0.019 Uiso 1 1 calc R . . H16B H 0.6015 0.5114 0.4732 0.019 Uiso 1 1 calc R . . C17 C 0.67668(11) 0.53428(19) 0.59398(9) 0.0165(3) Uani 1 1 d . . . C18 C 0.60969(12) 0.5912(2) 0.70268(9) 0.0219(3) Uani 1 1 d . . . H18A H 0.5659 0.6714 0.7128 0.026 Uiso 1 1 calc R . . H18B H 0.6749 0.6228 0.7327 0.026 Uiso 1 1 calc R . . C19 C 0.58784(12) 0.4344(2) 0.73441(10) 0.0234(4) Uani 1 1 d . . . H19A H 0.5240 0.4010 0.7038 0.035 Uiso 1 1 calc R . . H19B H 0.5915 0.4443 0.7920 0.035 Uiso 1 1 calc R . . H19C H 0.6339 0.3561 0.7281 0.035 Uiso 1 1 calc R . . C20 C 0.71502(10) 0.54911(18) 0.37809(9) 0.0148(3) Uani 1 1 d . . . C21 C 0.73682(11) 0.4846(2) 0.24947(9) 0.0196(3) Uani 1 1 d . . . H21A H 0.7870 0.4378 0.2290 0.024 Uiso 1 1 calc R . . H21B H 0.7354 0.5991 0.2389 0.024 Uiso 1 1 calc R . . C22 C 0.64208(12) 0.4136(2) 0.20450(10) 0.0242(4) Uani 1 1 d . . . H22A H 0.6415 0.3020 0.2185 0.036 Uiso 1 1 calc R . . H22B H 0.6320 0.4242 0.1459 0.036 Uiso 1 1 calc R . . H22C H 0.5915 0.4684 0.2200 0.036 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 0.01659(18) 0.01693(18) 0.01131(16) 0.00060(13) 0.00390(13) 0.00126(14) N1 0.0139(6) 0.0159(6) 0.0137(6) 0.0028(5) 0.0036(5) 0.0026(5) O1 0.0184(5) 0.0214(6) 0.0231(6) 0.0068(5) 0.0051(4) 0.0057(5) O2 0.0266(6) 0.0210(6) 0.0176(5) -0.0013(4) 0.0096(5) 0.0033(5) O3 0.0183(5) 0.0237(6) 0.0133(5) 0.0027(4) 0.0012(4) 0.0005(4) O4 0.0224(6) 0.0199(6) 0.0155(5) 0.0035(4) 0.0044(4) 0.0056(5) O5 0.0183(5) 0.0234(6) 0.0110(5) 0.0017(4) 0.0054(4) 0.0049(4) O6 0.0168(5) 0.0397(7) 0.0155(5) 0.0049(5) 0.0047(4) 0.0086(5) O7 0.0192(5) 0.0318(7) 0.0146(5) 0.0035(5) 0.0072(4) 0.0096(5) C1 0.0144(7) 0.0158(7) 0.0122(6) 0.0021(5) 0.0041(5) 0.0033(6) C2 0.0134(7) 0.0213(8) 0.0097(6) -0.0002(6) 0.0044(5) 0.0022(6) C3 0.0186(7) 0.0195(8) 0.0161(7) 0.0006(6) 0.0074(6) 0.0037(6) C4 0.0221(8) 0.0208(8) 0.0183(7) -0.0029(6) 0.0088(6) -0.0018(6) C5 0.0156(7) 0.0284(9) 0.0161(7) -0.0026(6) 0.0059(6) -0.0014(6) C6 0.0145(7) 0.0259(8) 0.0129(6) 0.0018(6) 0.0052(5) 0.0043(6) C7 0.0151(7) 0.0201(8) 0.0113(6) 0.0019(6) 0.0062(5) 0.0037(6) C8 0.0136(7) 0.0218(8) 0.0126(6) 0.0021(6) 0.0058(5) 0.0039(6) C9 0.0181(7) 0.0156(7) 0.0124(6) -0.0016(5) 0.0052(5) -0.0018(6) C10 0.0175(7) 0.0183(7) 0.0153(7) 0.0006(6) 0.0019(6) 0.0013(6) C11 0.0153(7) 0.0212(8) 0.0185(7) -0.0016(6) 0.0047(6) 0.0011(6) C12 0.0189(7) 0.0186(8) 0.0138(7) -0.0025(6) 0.0038(6) -0.0040(6) C13 0.0181(7) 0.0191(8) 0.0146(7) 0.0022(6) 0.0026(6) -0.0006(6) C14 0.0159(7) 0.0184(7) 0.0163(7) 0.0010(6) 0.0035(6) 0.0022(6) C15 0.0228(8) 0.0278(9) 0.0180(7) 0.0003(7) 0.0082(6) -0.0020(7) C16 0.0135(7) 0.0214(8) 0.0126(7) 0.0034(6) 0.0037(5) 0.0054(6) C17 0.0149(7) 0.0192(7) 0.0161(7) 0.0006(6) 0.0055(6) 0.0015(6) C18 0.0247(8) 0.0279(9) 0.0147(7) -0.0004(6) 0.0080(6) 0.0071(7) C19 0.0208(8) 0.0321(9) 0.0180(7) -0.0012(7) 0.0065(6) -0.0036(7) C20 0.0135(7) 0.0175(7) 0.0131(6) 0.0007(5) 0.0034(5) -0.0004(6) C21 0.0225(8) 0.0263(8) 0.0111(6) 0.0013(6) 0.0065(6) 0.0016(6) C22 0.0246(8) 0.0299(9) 0.0169(7) -0.0018(7) 0.0041(6) 0.0011(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4342(12) . ? S1 O3 1.4412(11) . ? S1 N1 1.6737(13) . ? S1 C9 1.7638(15) . ? N1 C8 1.4289(18) . ? N1 C1 1.4813(19) . ? O1 C8 1.2150(19) . ? O4 C20 1.2109(18) . ? O5 C20 1.3375(18) . ? O5 C21 1.4754(17) . ? O6 C17 1.2089(19) . ? O7 C17 1.3487(18) . ? O7 C18 1.4732(18) . ? C1 C2 1.530(2) . ? C1 C16 1.547(2) . ? C1 C20 1.5531(19) . ? C2 C3 1.389(2) . ? C2 C7 1.391(2) . ? C3 C4 1.404(2) . ? C3 H3 0.9500 . ? C4 C5 1.403(2) . ? C4 H4 0.9500 . ? C5 C6 1.396(2) . ? C5 H5 0.9500 . ? C6 C7 1.397(2) . ? C6 H6 0.9500 . ? C7 C8 1.483(2) . ? C9 C14 1.398(2) . ? C9 C10 1.400(2) . ? C10 C11 1.388(2) . ? C10 H10 0.9500 . ? C11 C12 1.401(2) . ? C11 H11 0.9500 . ? C12 C13 1.402(2) . ? C12 C15 1.513(2) . ? C13 C14 1.395(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.525(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C18 C19 1.511(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C21 C22 1.515(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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 _geom_angle_publ_flag O2 S1 O3 120.55(7) . . ? O2 S1 N1 107.47(7) . . ? O3 S1 N1 104.18(7) . . ? O2 S1 C9 109.42(7) . . ? O3 S1 C9 108.42(7) . . ? N1 S1 C9 105.78(7) . . ? C8 N1 C1 113.15(12) . . ? C8 N1 S1 124.79(11) . . ? C1 N1 S1 122.03(10) . . ? C20 O5 C21 116.28(12) . . ? C17 O7 C18 116.69(12) . . ? N1 C1 C2 101.07(11) . . ? N1 C1 C16 113.69(12) . . ? C2 C1 C16 112.37(12) . . ? N1 C1 C20 113.07(12) . . ? C2 C1 C20 108.05(12) . . ? C16 C1 C20 108.39(11) . . ? C3 C2 C7 121.43(14) . . ? C3 C2 C1 128.00(14) . . ? C7 C2 C1 110.57(13) . . ? C2 C3 C4 117.57(14) . . ? C2 C3 H3 121.2 . . ? C4 C3 H3 121.2 . . ? C5 C4 C3 121.14(15) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C6 C5 C4 120.72(15) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 117.81(14) . . ? C5 C6 H6 121.1 . . ? C7 C6 H6 121.1 . . ? C2 C7 C6 121.35(15) . . ? C2 C7 C8 109.72(13) . . ? C6 C7 C8 128.93(14) . . ? O1 C8 N1 124.97(14) . . ? O1 C8 C7 130.03(14) . . ? N1 C8 C7 105.00(12) . . ? C14 C9 C10 121.46(14) . . ? C14 C9 S1 119.97(12) . . ? C10 C9 S1 118.58(12) . . ? C11 C10 C9 118.68(14) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? C10 C11 C12 121.30(14) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C11 C12 C13 118.81(14) . . ? C11 C12 C15 119.70(14) . . ? C13 C12 C15 121.45(14) . . ? C14 C13 C12 121.03(14) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C9 118.67(14) . . ? C13 C14 H14 120.7 . . ? C9 C14 H14 120.7 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C1 115.05(12) . . ? C17 C16 H16A 108.5 . . ? C1 C16 H16A 108.5 . . ? C17 C16 H16B 108.5 . . ? C1 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? O6 C17 O7 124.39(14) . . ? O6 C17 C16 126.60(14) . . ? O7 C17 C16 108.98(12) . . ? O7 C18 C19 112.36(14) . . ? O7 C18 H18A 109.1 . . ? C19 C18 H18A 109.1 . . ? O7 C18 H18B 109.1 . . ? C19 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O4 C20 O5 125.74(13) . . ? O4 C20 C1 122.00(13) . . ? O5 C20 C1 112.13(12) . . ? O5 C21 C22 111.38(13) . . ? O5 C21 H21A 109.4 . . ? C22 C21 H21A 109.4 . . ? O5 C21 H21B 109.4 . . ? C22 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 _geom_torsion_publ_flag O2 S1 N1 C8 -40.97(13) . . . . ? O3 S1 N1 C8 -169.95(11) . . . . ? C9 S1 N1 C8 75.84(13) . . . . ? O2 S1 N1 C1 141.35(11) . . . . ? O3 S1 N1 C1 12.38(13) . . . . ? C9 S1 N1 C1 -101.83(12) . . . . ? C8 N1 C1 C2 7.02(15) . . . . ? S1 N1 C1 C2 -175.06(9) . . . . ? C8 N1 C1 C16 -113.60(14) . . . . ? S1 N1 C1 C16 64.32(15) . . . . ? C8 N1 C1 C20 122.26(13) . . . . ? S1 N1 C1 C20 -59.82(15) . . . . ? N1 C1 C2 C3 176.01(14) . . . . ? C16 C1 C2 C3 -62.44(19) . . . . ? C20 C1 C2 C3 57.09(19) . . . . ? N1 C1 C2 C7 -4.25(15) . . . . ? C16 C1 C2 C7 117.30(14) . . . . ? C20 C1 C2 C7 -123.17(13) . . . . ? C7 C2 C3 C4 -0.1(2) . . . . ? C1 C2 C3 C4 179.62(13) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C3 C4 C5 C6 -0.1(2) . . . . ? C4 C5 C6 C7 0.0(2) . . . . ? C3 C2 C7 C6 0.1(2) . . . . ? C1 C2 C7 C6 -179.69(13) . . . . ? C3 C2 C7 C8 -179.95(13) . . . . ? C1 C2 C7 C8 0.29(16) . . . . ? C5 C6 C7 C2 0.0(2) . . . . ? C5 C6 C7 C8 179.99(14) . . . . ? C1 N1 C8 O1 172.67(14) . . . . ? S1 N1 C8 O1 -5.2(2) . . . . ? C1 N1 C8 C7 -7.09(15) . . . . ? S1 N1 C8 C7 175.05(10) . . . . ? C2 C7 C8 O1 -175.72(15) . . . . ? C6 C7 C8 O1 4.3(3) . . . . ? C2 C7 C8 N1 4.02(16) . . . . ? C6 C7 C8 N1 -176.01(14) . . . . ? O2 S1 C9 C14 36.75(14) . . . . ? O3 S1 C9 C14 170.02(12) . . . . ? N1 S1 C9 C14 -78.73(14) . . . . ? O2 S1 C9 C10 -143.42(12) . . . . ? O3 S1 C9 C10 -10.15(15) . . . . ? N1 S1 C9 C10 101.09(13) . . . . ? C14 C9 C10 C11 1.5(2) . . . . ? S1 C9 C10 C11 -178.35(12) . . . . ? C9 C10 C11 C12 0.6(2) . . . . ? C10 C11 C12 C13 -2.2(2) . . . . ? C10 C11 C12 C15 175.72(15) . . . . ? C11 C12 C13 C14 1.7(2) . . . . ? C15 C12 C13 C14 -176.10(15) . . . . ? C12 C13 C14 C9 0.2(2) . . . . ? C10 C9 C14 C13 -1.9(2) . . . . ? S1 C9 C14 C13 177.95(12) . . . . ? N1 C1 C16 C17 54.29(17) . . . . ? C2 C1 C16 C17 -59.74(17) . . . . ? C20 C1 C16 C17 -179.07(13) . . . . ? C18 O7 C17 O6 7.7(2) . . . . ? C18 O7 C17 C16 -170.42(13) . . . . ? C1 C16 C17 O6 3.0(2) . . . . ? C1 C16 C17 O7 -178.96(13) . . . . ? C17 O7 C18 C19 -84.10(17) . . . . ? C21 O5 C20 O4 -5.8(2) . . . . ? C21 O5 C20 C1 178.33(12) . . . . ? N1 C1 C20 O4 154.43(14) . . . . ? C2 C1 C20 O4 -94.58(16) . . . . ? C16 C1 C20 O4 27.44(19) . . . . ? N1 C1 C20 O5 -29.52(17) . . . . ? C2 C1 C20 O5 81.47(15) . . . . ? C16 C1 C20 O5 -156.51(12) . . . . ? C20 O5 C21 C22 -77.53(17) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.35 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.390 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.050