data_150415_dpp_cf _audit_creation_date 2015-04-15 _audit_creation_method ; Olex2 1.2 (compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816) ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C44 H52 N2 O8 S2' _chemical_formula_sum 'C44 H52 N2 O8 S2' _chemical_formula_weight 801.00 _chemical_melting_point ? _chemical_oxdiff_formula 'c10 h10 n2 o8 s1' 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 'triclinic' _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 8.4348(7) _cell_length_b 10.0466(11) _cell_length_c 12.8543(14) _cell_angle_alpha 87.934(9) _cell_angle_beta 73.154(9) _cell_angle_gamma 76.337(8) _cell_volume 1012.43(18) _cell_formula_units_Z 1 _cell_measurement_reflns_used 1614 _cell_measurement_temperature 170 _cell_measurement_theta_max 29.5642 _cell_measurement_theta_min 2.9168 _exptl_absorpt_coefficient_mu 0.188 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.75634 _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 'dark red' _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 426 _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.18 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_unetI/netI 0.0667 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 6200 _diffrn_reflns_theta_full 25.35 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_min 2.92 _diffrn_ambient_temperature 170 _diffrn_detector_area_resol_mean 10.3592 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0871160000 _diffrn_orient_matrix_UB_12 0.0221729000 _diffrn_orient_matrix_UB_13 0.0300450000 _diffrn_orient_matrix_UB_21 -0.0074536000 _diffrn_orient_matrix_UB_22 0.0593272000 _diffrn_orient_matrix_UB_23 -0.0315282000 _diffrn_orient_matrix_UB_31 -0.0230346000 _diffrn_orient_matrix_UB_32 -0.0356948000 _diffrn_orient_matrix_UB_33 -0.0378327000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2552 _reflns_number_total 3692 _reflns_odcompleteness_completeness 99.71 _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 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.926 _refine_diff_density_min -0.889 _refine_diff_density_rms 0.077 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 256 _refine_ls_number_reflns 3692 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1121 _refine_ls_R_factor_gt 0.0786 _refine_ls_restrained_S_all 1.035 _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^)+(0.1212P)^2^+0.9876P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2001 _refine_ls_wR_factor_ref 0.2360 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C16(H16) 2.b Secondary CH2 refined with riding coordinates: C13(H13A,H13B), C15(H15A,H15B), C17(H17A,H17B), C19(H19A,H19B), C20(H20A, H20B), C21(H21A,H21B) 2.c Aromatic/amide H refined with riding coordinates: C5(H5), C6(H6), C9(H9), C10(H10) 2.d Idealised Me refined as rotating group: C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C22(H22A,H22B,H22C) ; _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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn S1 S 0.39048(13) 0.60817(10) 0.34077(8) 0.0400(3) Uani 1 d . . . O1 O -0.2453(4) 0.9627(3) 0.3859(2) 0.0445(7) Uani 1 d . . . O2 O 0.8506(3) 0.4308(3) 0.3664(2) 0.0370(7) Uani 1 d . . . O3 O 1.1524(4) 0.3294(3) 0.4106(3) 0.0604(9) Uani 1 d . . . O4 O 1.2210(3) 0.1589(3) 0.2856(2) 0.0407(7) Uani 1 d . . . N1 N 0.0252(4) 0.8410(3) 0.3861(3) 0.0342(8) Uani 1 d . . . C1 C -0.1208(5) 0.9515(4) 0.4199(3) 0.0350(9) Uani 1 d . . . C2 C 0.1479(5) 0.8497(4) 0.4370(3) 0.0317(8) Uani 1 d . . . C3 C 0.0813(5) 0.9679(4) 0.5042(3) 0.0312(8) Uani 1 d . . . C4 C 0.3103(5) 0.7560(4) 0.4233(3) 0.0328(9) Uani 1 d . . . C5 C 0.4285(5) 0.7728(4) 0.4743(3) 0.0395(10) Uani 1 d . . . H5 H 0.4093 0.8476 0.5231 0.047 Uiso 1 calc . . R C6 C 0.5787(5) 0.6694(4) 0.4473(3) 0.0384(9) Uani 1 d . . . H6 H 0.6706 0.6662 0.4767 0.046 Uiso 1 calc . . R C7 C 0.5798(5) 0.5733(4) 0.3742(3) 0.0340(9) Uani 1 d . . . C8 C 0.7114(5) 0.4539(4) 0.3280(3) 0.0358(9) Uani 1 d . . . C9 C 0.7324(5) 0.3550(4) 0.2536(4) 0.0444(10) Uani 1 d . . . H9 H 0.6547 0.3481 0.2145 0.053 Uiso 1 calc . . R C10 C 0.8908(5) 0.2643(4) 0.2449(3) 0.0438(10) Uani 1 d . . . H10 H 0.9403 0.1840 0.1993 0.053 Uiso 1 calc . . R C11 C 0.9587(5) 0.3132(4) 0.3138(3) 0.0370(9) Uani 1 d . . . C12 C 1.1186(5) 0.2700(4) 0.3437(3) 0.0383(9) Uani 1 d . . . C13 C 1.3859(5) 0.1119(4) 0.3071(4) 0.0437(10) Uani 1 d . . . H13A H 1.3698 0.0801 0.3824 0.052 Uiso 1 calc . . R H13B H 1.4449 0.1877 0.2983 0.052 Uiso 1 calc . . R C14 C 1.4894(6) -0.0034(5) 0.2275(4) 0.0551(12) Uani 1 d . . . H14A H 1.5070 0.0298 0.1534 0.083 Uiso 1 calc . . GR H14B H 1.4290 -0.0771 0.2361 0.083 Uiso 1 calc . . GR H14C H 1.6001 -0.0383 0.2411 0.083 Uiso 1 calc . . GR C15 C 0.0292(5) 0.7362(4) 0.3082(3) 0.0397(9) Uani 1 d . . . H15A H -0.0891 0.7315 0.3144 0.048 Uiso 1 calc . . R H15B H 0.0896 0.6459 0.3272 0.048 Uiso 1 calc . . R C16 C 0.1181(10) 0.7644(6) 0.1891(4) 0.083(2) Uani 1 d . . . H16 H 0.2417 0.7419 0.1852 0.100 Uiso 1 calc . . R C17 C 0.0908(13) 0.8925(7) 0.1523(5) 0.126(4) Uani 1 d . . . H17A H 0.0997 0.9531 0.2084 0.152 Uiso 1 calc . . R H17B H -0.0295 0.9178 0.1513 0.152 Uiso 1 calc . . R C18 C 0.1944(8) 0.9317(6) 0.0452(4) 0.0736(16) Uani 1 d . . . H18A H 0.1987 0.8682 -0.0122 0.110 Uiso 1 calc . . GR H18B H 0.3104 0.9272 0.0481 0.110 Uiso 1 calc . . GR H18C H 0.1421 1.0252 0.0295 0.110 Uiso 1 calc . . GR C19 C 0.1050(11) 0.6539(6) 0.1150(5) 0.091(2) Uani 1 d . . . H19A H -0.0124 0.6401 0.1398 0.109 Uiso 1 calc . . R H19B H 0.1232 0.6884 0.0404 0.109 Uiso 1 calc . . R C20 C 0.2258(8) 0.5192(6) 0.1104(4) 0.0729(17) Uani 1 d . . . H20A H 0.1981 0.4779 0.1826 0.087 Uiso 1 calc . . R H20B H 0.3428 0.5331 0.0942 0.087 Uiso 1 calc . . R C21 C 0.2213(9) 0.4203(6) 0.0251(5) 0.0833(19) Uani 1 d . . . H21A H 0.1070 0.4002 0.0451 0.100 Uiso 1 calc . . R H21B H 0.2384 0.4652 -0.0458 0.100 Uiso 1 calc . . R C22 C 0.3484(11) 0.2925(7) 0.0130(6) 0.110(3) Uani 1 d . . . H22A H 0.3283 0.2289 -0.0351 0.164 Uiso 1 calc . . GR H22B H 0.3411 0.2525 0.0844 0.164 Uiso 1 calc . . GR H22C H 0.4620 0.3096 -0.0185 0.164 Uiso 1 calc . . GR 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 0.0314(6) 0.0452(6) 0.0467(6) -0.0068(4) -0.0203(5) -0.0027(4) O1 0.0307(16) 0.0571(18) 0.0526(17) -0.0105(13) -0.0236(14) -0.0072(13) O2 0.0289(15) 0.0420(15) 0.0431(15) -0.0010(11) -0.0177(12) -0.0045(12) O3 0.045(2) 0.065(2) 0.077(2) -0.0201(17) -0.0363(18) 0.0026(16) O4 0.0238(15) 0.0504(16) 0.0483(16) -0.0026(12) -0.0152(13) -0.0033(12) N1 0.0262(18) 0.0398(17) 0.0404(18) -0.0059(13) -0.0153(14) -0.0071(14) C1 0.029(2) 0.043(2) 0.037(2) -0.0021(16) -0.0145(17) -0.0094(17) C2 0.026(2) 0.042(2) 0.0310(19) 0.0015(15) -0.0119(16) -0.0114(16) C3 0.0209(19) 0.044(2) 0.0320(19) 0.0010(15) -0.0121(15) -0.0084(16) C4 0.024(2) 0.042(2) 0.034(2) 0.0001(16) -0.0100(16) -0.0090(16) C5 0.032(2) 0.046(2) 0.044(2) -0.0036(18) -0.0167(19) -0.0091(18) C6 0.027(2) 0.046(2) 0.048(2) -0.0008(18) -0.0207(18) -0.0075(17) C7 0.025(2) 0.040(2) 0.038(2) 0.0031(16) -0.0124(17) -0.0066(16) C8 0.026(2) 0.046(2) 0.038(2) 0.0059(17) -0.0148(17) -0.0065(17) C9 0.033(2) 0.052(2) 0.051(2) -0.0068(19) -0.020(2) -0.0028(19) C10 0.033(2) 0.049(2) 0.049(2) -0.0073(19) -0.017(2) -0.0027(19) C11 0.032(2) 0.039(2) 0.040(2) 0.0012(16) -0.0142(18) -0.0048(17) C12 0.031(2) 0.043(2) 0.042(2) 0.0006(17) -0.0159(18) -0.0041(18) C13 0.022(2) 0.056(3) 0.053(2) 0.0037(19) -0.0167(19) -0.0032(18) C14 0.030(2) 0.074(3) 0.054(3) 0.000(2) -0.015(2) 0.007(2) C15 0.037(2) 0.044(2) 0.046(2) -0.0063(17) -0.0206(19) -0.0113(18) C16 0.150(7) 0.067(3) 0.047(3) -0.002(2) -0.043(4) -0.035(4) C17 0.219(11) 0.116(6) 0.051(4) -0.001(4) -0.007(5) -0.092(6) C18 0.067(4) 0.107(4) 0.051(3) 0.013(3) -0.021(3) -0.026(3) C19 0.157(7) 0.078(4) 0.056(3) -0.011(3) -0.053(4) -0.035(4) C20 0.074(4) 0.087(4) 0.064(3) -0.019(3) -0.010(3) -0.040(3) C21 0.101(5) 0.073(4) 0.078(4) -0.021(3) -0.024(4) -0.025(4) C22 0.097(6) 0.103(5) 0.110(6) -0.027(4) -0.012(5) -0.006(4) _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 C4 1.736(4) . ? S1 C7 1.727(4) . ? O1 C1 1.230(5) . ? O2 C8 1.368(5) . ? O2 C11 1.370(5) . ? O3 C12 1.199(5) . ? O4 C12 1.334(5) . ? O4 C13 1.462(5) . ? N1 C1 1.420(5) . ? N1 C2 1.396(5) . ? N1 C15 1.467(5) . ? C1 C3 1.446(5) 2_576 ? C2 C3 1.397(5) . ? C2 C4 1.434(5) . ? C3 C1 1.446(5) 2_576 ? C3 C3 1.404(7) 2_576 ? C4 C5 1.385(5) . ? C5 H5 0.9500 . ? C5 C6 1.398(6) . ? C6 H6 0.9500 . ? C6 C7 1.368(5) . ? C7 C8 1.437(5) . ? C8 C9 1.349(6) . ? C9 H9 0.9500 . ? C9 C10 1.405(6) . ? C10 H10 0.9500 . ? C10 C11 1.346(6) . ? C11 C12 1.472(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 C14 1.497(6) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C15 C16 1.545(7) . ? C16 H16 1.0000 . ? C16 C17 1.347(8) . ? C16 C19 1.532(7) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C17 C18 1.497(8) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C19 C20 1.480(8) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C20 C21 1.521(7) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 C22 1.445(9) . ? 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 C7 S1 C4 92.14(18) . . ? C8 O2 C11 106.1(3) . . ? C12 O4 C13 115.2(3) . . ? C1 N1 C15 119.5(3) . . ? C2 N1 C1 111.4(3) . . ? C2 N1 C15 129.1(3) . . ? O1 C1 N1 122.1(3) . . ? O1 C1 C3 133.5(4) . 2_576 ? N1 C1 C3 104.4(3) . 2_576 ? N1 C2 C3 106.4(3) . . ? N1 C2 C4 127.0(3) . . ? C3 C2 C4 126.7(3) . . ? C2 C3 C1 142.2(3) . 2_576 ? C2 C3 C3 109.7(4) . 2_576 ? C3 C3 C1 108.1(4) 2_576 2_576 ? C2 C4 S1 126.2(3) . . ? C5 C4 S1 109.8(3) . . ? C5 C4 C2 124.0(4) . . ? C4 C5 H5 123.1 . . ? C4 C5 C6 113.7(4) . . ? C6 C5 H5 123.1 . . ? C5 C6 H6 123.4 . . ? C7 C6 C5 113.1(4) . . ? C7 C6 H6 123.4 . . ? C6 C7 S1 111.1(3) . . ? C6 C7 C8 128.7(4) . . ? C8 C7 S1 120.2(3) . . ? O2 C8 C7 115.1(3) . . ? C9 C8 O2 109.9(3) . . ? C9 C8 C7 134.9(4) . . ? C8 C9 H9 126.5 . . ? C8 C9 C10 107.1(4) . . ? C10 C9 H9 126.5 . . ? C9 C10 H10 126.7 . . ? C11 C10 C9 106.7(4) . . ? C11 C10 H10 126.7 . . ? O2 C11 C12 114.8(3) . . ? C10 C11 O2 110.3(4) . . ? C10 C11 C12 134.9(4) . . ? O3 C12 O4 124.8(4) . . ? O3 C12 C11 123.7(4) . . ? O4 C12 C11 111.5(3) . . ? O4 C13 H13A 110.2 . . ? O4 C13 H13B 110.2 . . ? O4 C13 C14 107.7(3) . . ? H13A C13 H13B 108.5 . . ? C14 C13 H13A 110.2 . . ? C14 C13 H13B 110.2 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 H15A 109.0 . . ? N1 C15 H15B 109.0 . . ? N1 C15 C16 113.1(3) . . ? H15A C15 H15B 107.8 . . ? C16 C15 H15A 109.0 . . ? C16 C15 H15B 109.0 . . ? C15 C16 H16 103.6 . . ? C17 C16 C15 120.4(5) . . ? C17 C16 H16 103.6 . . ? C17 C16 C19 115.0(5) . . ? C19 C16 C15 108.5(5) . . ? C19 C16 H16 103.6 . . ? C16 C17 H17A 106.5 . . ? C16 C17 H17B 106.5 . . ? C16 C17 C18 123.1(7) . . ? H17A C17 H17B 106.5 . . ? C18 C17 H17A 106.5 . . ? C18 C17 H17B 106.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 108.4 . . ? C16 C19 H19B 108.4 . . ? H19A C19 H19B 107.4 . . ? C20 C19 C16 115.7(5) . . ? C20 C19 H19A 108.4 . . ? C20 C19 H19B 108.4 . . ? C19 C20 H20A 109.0 . . ? C19 C20 H20B 109.0 . . ? C19 C20 C21 112.9(5) . . ? H20A C20 H20B 107.8 . . ? C21 C20 H20A 109.0 . . ? C21 C20 H20B 109.0 . . ? C20 C21 H21A 108.8 . . ? C20 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C22 C21 C20 113.7(6) . . ? C22 C21 H21A 108.8 . . ? C22 C21 H21B 108.8 . . ? 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 . . ? 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 C4 C5 C6 0.0(4) . . . . ? S1 C7 C8 O2 -175.3(3) . . . . ? S1 C7 C8 C9 4.5(6) . . . . ? O2 C8 C9 C10 0.6(5) . . . . ? O2 C11 C12 O3 2.0(6) . . . . ? O2 C11 C12 O4 -176.9(3) . . . . ? N1 C2 C3 C1 -179.8(5) . . . 2_576 ? N1 C2 C3 C3 0.3(5) . . . 2_576 ? N1 C2 C4 S1 -0.8(6) . . . . ? N1 C2 C4 C5 178.1(4) . . . . ? N1 C15 C16 C17 -41.1(9) . . . . ? N1 C15 C16 C19 -176.6(5) . . . . ? C1 N1 C2 C3 -0.4(4) . . . . ? C1 N1 C2 C4 179.6(3) . . . . ? C1 N1 C15 C16 94.9(5) . . . . ? C2 N1 C1 O1 -179.1(4) . . . . ? C2 N1 C1 C3 0.4(4) . . . 2_576 ? C2 N1 C15 C16 -86.2(5) . . . . ? C2 C4 C5 C6 -179.1(4) . . . . ? C3 C2 C4 S1 179.2(3) . . . . ? C3 C2 C4 C5 -1.9(6) . . . . ? C4 S1 C7 C6 1.4(3) . . . . ? C4 S1 C7 C8 -179.9(3) . . . . ? C4 C2 C3 C1 0.2(8) . . . 2_576 ? C4 C2 C3 C3 -179.7(4) . . . 2_576 ? C4 C5 C6 C7 1.0(5) . . . . ? C5 C6 C7 S1 -1.6(4) . . . . ? C5 C6 C7 C8 179.8(4) . . . . ? C6 C7 C8 O2 3.2(6) . . . . ? C6 C7 C8 C9 -177.0(4) . . . . ? C7 S1 C4 C2 178.3(3) . . . . ? C7 S1 C4 C5 -0.8(3) . . . . ? C7 C8 C9 C10 -179.2(4) . . . . ? C8 O2 C11 C10 0.2(4) . . . . ? C8 O2 C11 C12 179.8(3) . . . . ? C8 C9 C10 C11 -0.5(5) . . . . ? C9 C10 C11 O2 0.2(5) . . . . ? C9 C10 C11 C12 -179.4(4) . . . . ? C10 C11 C12 O3 -178.5(5) . . . . ? C10 C11 C12 O4 2.6(7) . . . . ? C11 O2 C8 C7 179.4(3) . . . . ? C11 O2 C8 C9 -0.5(4) . . . . ? C12 O4 C13 C14 -174.3(3) . . . . ? C13 O4 C12 O3 -1.1(6) . . . . ? C13 O4 C12 C11 177.8(3) . . . . ? C15 N1 C1 O1 0.0(6) . . . . ? C15 N1 C1 C3 179.5(3) . . . 2_576 ? C15 N1 C2 C3 -179.4(3) . . . . ? C15 N1 C2 C4 0.6(6) . . . . ? C15 C16 C17 C18 169.0(6) . . . . ? C15 C16 C19 C20 -78.0(7) . . . . ? C16 C19 C20 C21 -172.8(5) . . . . ? C17 C16 C19 C20 143.9(8) . . . . ? C19 C16 C17 C18 -58.3(12) . . . . ? C19 C20 C21 C22 175.0(6) . . . . ?