data_exp_2476 _audit_creation_date 2014-10-27 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common '1,2,4-thiadiazinane 6b' _chemical_name_systematic ; Ethyl rel(4bR,5R,13bS)-4b,5,9,13b,15,16-hexahydro-8H-[1,2,4]thiadiazino[3,2-a:5,4-a']diisoquinoline-5-carboxylate 6,6-dioxide ; _chemical_formula_moiety 'C22 H24 N2 O4 S' _chemical_formula_sum 'C22 H24 N2 O4 S' _chemical_formula_weight 412.49 _chemical_melting_point '146-148 deg' 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' _space_group_crystal_system 'monoclinic' _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.9160(13) _cell_length_b 13.6054(10) _cell_length_c 17.845(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.441(14) _cell_angle_gamma 90.00 _cell_volume 1916.1(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3619 _cell_measurement_temperature 106.7 _cell_measurement_theta_max 29.4867 _cell_measurement_theta_min 2.8982 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.94324 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'colorless' _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_meas 'none' _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'block' _exptl_crystal_F_000 872 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.34 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_unetI/netI 0.0391 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 9331 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.90 _diffrn_ambient_temperature 106.7 _diffrn_detector_area_resol_mean 16.0971 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -29.00 19.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -13.4480 -94.0000 -170.0000 48 #__ type_ start__ end____ width___ exp.time_ 2 omega -13.00 12.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -13.4480 -94.0000 59.0000 25 #__ type_ start__ end____ width___ exp.time_ 3 omega -45.00 -17.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 18.6043 -37.0000 -90.0000 28 #__ type_ start__ end____ width___ exp.time_ 4 omega -1.00 67.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 18.6043 37.0000 -30.0000 68 #__ type_ start__ end____ width___ exp.time_ 5 omega 3.00 88.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 18.6043 37.0000 90.0000 85 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0182781000 _diffrn_orient_matrix_UB_12 0.0463763000 _diffrn_orient_matrix_UB_13 -0.0155933000 _diffrn_orient_matrix_UB_21 -0.0208868000 _diffrn_orient_matrix_UB_22 0.0234275000 _diffrn_orient_matrix_UB_23 0.0335924000 _diffrn_orient_matrix_UB_31 0.0855329000 _diffrn_orient_matrix_UB_32 -0.0042041000 _diffrn_orient_matrix_UB_33 0.0147901000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3195 _reflns_number_total 3761 _reflns_odcompleteness_completeness 99.78 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.292 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.051 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 263 _refine_ls_number_reflns 3761 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0373 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0342P)^2^+0.9081P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0838 _refine_ls_wR_factor_ref 0.0897 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.79080(5) 0.70134(3) 0.01507(2) 0.01527(12) Uani 1 1 d . . . O1 O 0.71680(15) 0.73488(9) 0.08138(6) 0.0210(3) Uani 1 1 d . . . O4 O 0.64684(15) 0.48425(9) -0.08303(6) 0.0187(3) Uani 1 1 d . . . O3 O 0.74754(15) 0.60424(9) -0.15431(7) 0.0218(3) Uani 1 1 d . . . O2 O 0.93374(15) 0.63667(9) 0.02205(7) 0.0208(3) Uani 1 1 d . . . N1 N 0.83894(17) 0.79760(10) -0.03218(8) 0.0142(3) Uani 1 1 d . . . N2 N 0.55992(17) 0.81470(10) -0.10412(7) 0.0133(3) Uani 1 1 d . . . C13 C 0.1976(2) 0.66211(13) -0.24542(10) 0.0182(4) Uani 1 1 d . . . H13 H 0.1738 0.6835 -0.2946 0.022 Uiso 1 1 calc R . . C11 C 0.4091(2) 0.80090(13) -0.22681(9) 0.0166(4) Uani 1 1 d . . . H11A H 0.3418 0.8592 -0.2194 0.020 Uiso 1 1 calc R . . H11B H 0.4214 0.7941 -0.2802 0.020 Uiso 1 1 calc R . . C9 C 0.9703(2) 0.79412(13) -0.08656(10) 0.0161(4) Uani 1 1 d . . . H9A H 0.9203 0.7765 -0.1361 0.019 Uiso 1 1 calc R . . H9B H 1.0561 0.7458 -0.0711 0.019 Uiso 1 1 calc R . . C20 C 0.6804(2) 0.57816(13) -0.09978(9) 0.0152(4) Uani 1 1 d . . . C16 C 0.2669(2) 0.59708(13) -0.10003(10) 0.0161(4) Uani 1 1 d . . . H16 H 0.2898 0.5753 -0.0509 0.019 Uiso 1 1 calc R . . C17 C 0.3547(2) 0.67789(12) -0.12550(9) 0.0138(3) Uani 1 1 d . . . C19 C 0.6177(2) 0.64527(12) -0.04004(9) 0.0139(3) Uani 1 1 d . . . H19 H 0.5575 0.6038 -0.0059 0.017 Uiso 1 1 calc R . . C14 C 0.1120(2) 0.58175(14) -0.21980(10) 0.0197(4) Uani 1 1 d . . . H14 H 0.0312 0.5497 -0.2516 0.024 Uiso 1 1 calc R . . C3 C 0.6291(2) 1.03465(13) -0.08942(9) 0.0165(4) Uani 1 1 d . . . H3 H 0.5174 1.0226 -0.0795 0.020 Uiso 1 1 calc R . . C10 C 0.5827(2) 0.81257(13) -0.18523(9) 0.0150(4) Uani 1 1 d . . . H10A H 0.6553 0.7581 -0.1968 0.018 Uiso 1 1 calc R . . H10B H 0.6353 0.8731 -0.2003 0.018 Uiso 1 1 calc R . . C2 C 0.7477(2) 0.95898(13) -0.08130(9) 0.0143(4) Uani 1 1 d . . . C7 C 0.9155(2) 0.97615(13) -0.09729(9) 0.0162(4) Uani 1 1 d . . . C5 C 0.8416(2) 1.14466(14) -0.12782(10) 0.0218(4) Uani 1 1 d . . . H5 H 0.8736 1.2068 -0.1433 0.026 Uiso 1 1 calc R . . C12 C 0.3191(2) 0.71162(13) -0.19885(9) 0.0151(4) Uani 1 1 d . . . C21 C 0.6904(2) 0.41061(14) -0.13752(10) 0.0233(4) Uani 1 1 d . . . H21A H 0.7124 0.3483 -0.1122 0.028 Uiso 1 1 calc R . . H21B H 0.7926 0.4305 -0.1601 0.028 Uiso 1 1 calc R . . C8 C 1.0479(2) 0.89601(13) -0.08797(10) 0.0179(4) Uani 1 1 d . . . H8A H 1.1174 0.9068 -0.0415 0.022 Uiso 1 1 calc R . . H8B H 1.1210 0.8998 -0.1291 0.022 Uiso 1 1 calc R . . C4 C 0.6752(2) 1.12738(13) -0.11204(10) 0.0198(4) Uani 1 1 d . . . H4 H 0.5955 1.1777 -0.1167 0.024 Uiso 1 1 calc R . . C22 C 0.5486(2) 0.39842(16) -0.19784(10) 0.0277(5) Uani 1 1 d . . . H22A H 0.5750 0.3456 -0.2306 0.042 Uiso 1 1 calc R . . H22B H 0.5347 0.4582 -0.2263 0.042 Uiso 1 1 calc R . . H22C H 0.4455 0.3837 -0.1751 0.042 Uiso 1 1 calc R . . C1 C 0.6886(2) 0.86087(12) -0.05336(9) 0.0142(4) Uani 1 1 d . . . H1 H 0.6351 0.8743 -0.0067 0.017 Uiso 1 1 calc R . . C6 C 0.9597(2) 1.06973(13) -0.12062(10) 0.0199(4) Uani 1 1 d . . . H6 H 1.0707 1.0821 -0.1316 0.024 Uiso 1 1 calc R . . C15 C 0.1466(2) 0.54897(14) -0.14676(10) 0.0192(4) Uani 1 1 d . . . H15 H 0.0892 0.4950 -0.1293 0.023 Uiso 1 1 calc R . . C18 C 0.4879(2) 0.72714(12) -0.07171(9) 0.0138(3) Uani 1 1 d . . . H18 H 0.4283 0.7498 -0.0288 0.017 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 0.0179(2) 0.0142(2) 0.0132(2) 0.00100(17) -0.00171(16) -0.00051(17) O1 0.0278(7) 0.0214(7) 0.0138(6) -0.0006(5) 0.0009(5) -0.0029(6) O4 0.0266(6) 0.0117(6) 0.0178(6) -0.0010(5) 0.0010(5) -0.0002(5) O3 0.0236(6) 0.0202(7) 0.0227(7) -0.0007(6) 0.0084(5) 0.0003(5) O2 0.0205(6) 0.0169(7) 0.0242(7) 0.0034(6) -0.0035(5) 0.0013(5) N1 0.0139(7) 0.0132(7) 0.0158(7) 0.0005(6) 0.0025(6) 0.0000(6) N2 0.0158(7) 0.0116(7) 0.0124(7) 0.0011(6) 0.0012(5) -0.0009(6) C13 0.0170(8) 0.0209(9) 0.0163(8) 0.0009(7) -0.0008(7) 0.0020(7) C11 0.0186(8) 0.0173(9) 0.0138(8) 0.0027(7) 0.0004(7) 0.0006(7) C9 0.0146(8) 0.0161(9) 0.0179(8) -0.0011(7) 0.0027(7) 0.0019(7) C20 0.0132(8) 0.0141(9) 0.0176(9) 0.0001(7) -0.0032(7) 0.0014(7) C16 0.0143(8) 0.0168(9) 0.0174(8) 0.0031(7) 0.0018(7) 0.0026(7) C17 0.0118(8) 0.0123(8) 0.0172(8) -0.0018(7) 0.0011(6) 0.0030(7) C19 0.0150(8) 0.0127(8) 0.0142(8) 0.0014(7) 0.0021(6) -0.0011(7) C14 0.0160(8) 0.0193(10) 0.0232(9) -0.0022(8) -0.0030(7) -0.0020(7) C3 0.0177(8) 0.0165(9) 0.0152(8) -0.0024(7) -0.0003(7) -0.0011(7) C10 0.0161(8) 0.0150(9) 0.0141(8) 0.0011(7) 0.0029(6) 0.0000(7) C2 0.0183(8) 0.0139(9) 0.0104(8) -0.0035(7) -0.0003(6) -0.0010(7) C7 0.0183(8) 0.0164(9) 0.0140(8) -0.0020(7) 0.0015(7) -0.0015(7) C5 0.0294(10) 0.0144(9) 0.0214(9) 0.0018(8) 0.0017(8) -0.0047(8) C12 0.0133(8) 0.0146(9) 0.0176(8) 0.0002(7) 0.0029(6) 0.0022(7) C21 0.0298(10) 0.0142(9) 0.0264(10) -0.0054(8) 0.0046(8) 0.0023(8) C8 0.0161(8) 0.0207(10) 0.0174(9) -0.0008(8) 0.0036(7) -0.0011(7) C4 0.0240(9) 0.0157(9) 0.0191(9) -0.0024(8) -0.0035(7) 0.0024(8) C22 0.0311(10) 0.0301(11) 0.0227(10) -0.0096(9) 0.0066(8) -0.0091(9) C1 0.0147(8) 0.0141(9) 0.0140(8) -0.0011(7) 0.0025(6) 0.0016(7) C6 0.0201(9) 0.0196(10) 0.0202(9) -0.0018(8) 0.0033(7) -0.0046(7) C15 0.0164(8) 0.0157(9) 0.0255(9) 0.0038(8) 0.0008(7) -0.0005(7) C18 0.0141(8) 0.0135(9) 0.0141(8) 0.0004(7) 0.0033(6) 0.0015(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 O1 1.4348(13) . ? S1 O2 1.4311(13) . ? S1 N1 1.6190(15) . ? S1 C19 1.7939(16) . ? O4 C20 1.343(2) . ? O4 C21 1.456(2) . ? O3 C20 1.198(2) . ? N1 C9 1.477(2) . ? N1 C1 1.493(2) . ? N2 C10 1.473(2) . ? N2 C1 1.453(2) . ? N2 C18 1.459(2) . ? C13 H13 0.9300 . ? C13 C14 1.383(3) . ? C13 C12 1.395(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C10 1.519(2) . ? C11 C12 1.512(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C8 1.517(2) . ? C20 C19 1.516(2) . ? C16 H16 0.9300 . ? C16 C17 1.395(2) . ? C16 C15 1.381(2) . ? C17 C12 1.395(2) . ? C17 C18 1.525(2) . ? C19 H19 0.9800 . ? C19 C18 1.589(2) . ? C14 H14 0.9300 . ? C14 C15 1.385(2) . ? C3 H3 0.9300 . ? C3 C2 1.393(2) . ? C3 C4 1.382(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C2 C7 1.400(2) . ? C2 C1 1.512(2) . ? C7 C8 1.512(2) . ? C7 C6 1.393(2) . ? C5 H5 0.9300 . ? C5 C4 1.388(3) . ? C5 C6 1.383(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 C22 1.503(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C4 H4 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C1 H1 0.9800 . ? C6 H6 0.9300 . ? C15 H15 0.9300 . ? C18 H18 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 O1 S1 N1 107.45(8) . . ? O1 S1 C19 104.12(8) . . ? O2 S1 O1 119.62(7) . . ? O2 S1 N1 109.04(7) . . ? O2 S1 C19 110.58(8) . . ? N1 S1 C19 105.02(7) . . ? C20 O4 C21 116.41(14) . . ? C9 N1 S1 121.49(12) . . ? C9 N1 C1 116.09(13) . . ? C1 N1 S1 112.53(11) . . ? C1 N2 C10 119.20(13) . . ? C1 N2 C18 112.50(12) . . ? C18 N2 C10 117.05(13) . . ? C14 C13 H13 119.4 . . ? C14 C13 C12 121.19(16) . . ? C12 C13 H13 119.4 . . ? H11A C11 H11B 108.1 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? C12 C11 C10 110.76(14) . . ? N1 C9 H9A 110.4 . . ? N1 C9 H9B 110.4 . . ? N1 C9 C8 106.75(14) . . ? H9A C9 H9B 108.6 . . ? C8 C9 H9A 110.4 . . ? C8 C9 H9B 110.4 . . ? O4 C20 C19 109.58(14) . . ? O3 C20 O4 124.77(16) . . ? O3 C20 C19 125.64(16) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C15 C16 C17 120.94(16) . . ? C16 C17 C18 118.59(15) . . ? C12 C17 C16 119.69(15) . . ? C12 C17 C18 121.72(15) . . ? S1 C19 H19 107.0 . . ? C20 C19 S1 111.34(11) . . ? C20 C19 H19 107.0 . . ? C20 C19 C18 114.19(13) . . ? C18 C19 S1 110.02(11) . . ? C18 C19 H19 107.0 . . ? C13 C14 H14 120.0 . . ? C13 C14 C15 119.98(16) . . ? C15 C14 H14 120.0 . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C4 C3 C2 120.93(16) . . ? N2 C10 C11 107.87(13) . . ? N2 C10 H10A 110.1 . . ? N2 C10 H10B 110.1 . . ? C11 C10 H10A 110.1 . . ? C11 C10 H10B 110.1 . . ? H10A C10 H10B 108.4 . . ? C3 C2 C7 119.86(16) . . ? C3 C2 C1 117.64(15) . . ? C7 C2 C1 122.49(15) . . ? C2 C7 C8 121.18(15) . . ? C6 C7 C2 118.54(16) . . ? C6 C7 C8 120.27(15) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C6 C5 C4 120.13(17) . . ? C13 C12 C11 120.80(15) . . ? C13 C12 C17 118.69(16) . . ? C17 C12 C11 120.50(15) . . ? O4 C21 H21A 109.5 . . ? O4 C21 H21B 109.5 . . ? O4 C21 C22 110.61(15) . . ? H21A C21 H21B 108.1 . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? C9 C8 H8A 109.1 . . ? C9 C8 H8B 109.1 . . ? C7 C8 C9 112.49(14) . . ? C7 C8 H8A 109.1 . . ? C7 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C3 C4 C5 119.33(17) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N1 C1 C2 109.39(13) . . ? N1 C1 H1 106.3 . . ? N2 C1 N1 114.53(13) . . ? N2 C1 C2 113.33(13) . . ? N2 C1 H1 106.3 . . ? C2 C1 H1 106.3 . . ? C7 C6 H6 119.4 . . ? C5 C6 C7 121.21(16) . . ? C5 C6 H6 119.4 . . ? C16 C15 C14 119.50(17) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? N2 C18 C17 112.43(13) . . ? N2 C18 C19 116.82(13) . . ? N2 C18 H18 106.2 . . ? C17 C18 C19 108.21(13) . . ? C17 C18 H18 106.2 . . ? C19 C18 H18 106.2 . . ? 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 S1 N1 C9 C8 -150.27(12) . . . . ? S1 N1 C1 N2 -64.17(16) . . . . ? S1 N1 C1 C2 167.37(11) . . . . ? S1 C19 C18 N2 45.31(17) . . . . ? S1 C19 C18 C17 173.36(11) . . . . ? O1 S1 N1 C9 156.95(12) . . . . ? O1 S1 N1 C1 -58.71(12) . . . . ? O1 S1 C19 C20 -162.07(12) . . . . ? O1 S1 C19 C18 70.30(12) . . . . ? O4 C20 C19 S1 111.13(13) . . . . ? O4 C20 C19 C18 -123.53(14) . . . . ? O3 C20 C19 S1 -69.84(19) . . . . ? O3 C20 C19 C18 55.5(2) . . . . ? O2 S1 N1 C9 25.91(14) . . . . ? O2 S1 N1 C1 170.25(10) . . . . ? O2 S1 C19 C20 -32.36(14) . . . . ? O2 S1 C19 C18 -159.99(11) . . . . ? N1 S1 C19 C20 85.13(13) . . . . ? N1 S1 C19 C18 -42.51(13) . . . . ? N1 C9 C8 C7 -49.20(18) . . . . ? C13 C14 C15 C16 0.0(3) . . . . ? C9 N1 C1 N2 82.22(17) . . . . ? C9 N1 C1 C2 -46.24(18) . . . . ? C20 O4 C21 C22 -85.81(18) . . . . ? C20 C19 C18 N2 -80.73(18) . . . . ? C20 C19 C18 C17 47.33(18) . . . . ? C16 C17 C12 C13 -1.1(2) . . . . ? C16 C17 C12 C11 178.20(15) . . . . ? C16 C17 C18 N2 -175.73(14) . . . . ? C16 C17 C18 C19 53.76(19) . . . . ? C17 C16 C15 C14 -0.3(3) . . . . ? C19 S1 N1 C9 -92.62(13) . . . . ? C19 S1 N1 C1 51.72(12) . . . . ? C14 C13 C12 C11 -178.55(16) . . . . ? C14 C13 C12 C17 0.7(3) . . . . ? C3 C2 C7 C8 179.10(15) . . . . ? C3 C2 C7 C6 0.4(2) . . . . ? C3 C2 C1 N1 -167.40(14) . . . . ? C3 C2 C1 N2 63.47(19) . . . . ? C10 N2 C1 N1 -81.24(18) . . . . ? C10 N2 C1 C2 45.22(19) . . . . ? C10 N2 C18 C17 -35.59(18) . . . . ? C10 N2 C18 C19 90.39(17) . . . . ? C10 C11 C12 C13 -153.06(16) . . . . ? C10 C11 C12 C17 27.7(2) . . . . ? C2 C3 C4 C5 0.9(3) . . . . ? C2 C7 C8 C9 19.4(2) . . . . ? C2 C7 C6 C5 0.2(3) . . . . ? C7 C2 C1 N1 11.2(2) . . . . ? C7 C2 C1 N2 -117.97(17) . . . . ? C12 C13 C14 C15 -0.2(3) . . . . ? C12 C11 C10 N2 -54.72(18) . . . . ? C12 C17 C18 N2 4.2(2) . . . . ? C12 C17 C18 C19 -126.27(16) . . . . ? C21 O4 C20 O3 -2.6(2) . . . . ? C21 O4 C20 C19 176.49(13) . . . . ? C8 C7 C6 C5 -178.48(16) . . . . ? C4 C3 C2 C7 -1.0(2) . . . . ? C4 C3 C2 C1 177.61(15) . . . . ? C4 C5 C6 C7 -0.3(3) . . . . ? C1 N1 C9 C8 66.57(17) . . . . ? C1 N2 C10 C11 -156.96(14) . . . . ? C1 N2 C18 C17 -179.14(13) . . . . ? C1 N2 C18 C19 -53.16(18) . . . . ? C1 C2 C7 C8 0.6(2) . . . . ? C1 C2 C7 C6 -178.08(15) . . . . ? C6 C7 C8 C9 -161.99(15) . . . . ? C6 C5 C4 C3 -0.2(3) . . . . ? C15 C16 C17 C12 0.9(3) . . . . ? C15 C16 C17 C18 -179.14(16) . . . . ? C18 N2 C10 C11 61.99(18) . . . . ? C18 N2 C1 N1 61.46(18) . . . . ? C18 N2 C1 C2 -172.09(13) . . . . ? C18 C17 C12 C13 178.97(15) . . . . ? C18 C17 C12 C11 -1.8(2) . . . . ?