#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006871.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2006871 loop_ _publ_author_name 'Bolte, M.' _publ_section_title ; (2S,3R,4R,5R,SS)-2-Benzyl-3-hydroxy-5-{N-[(S)-1-hydroxy-3-methylbut-2-yl]-4-methylphenylsulfonimidoylmethyl}-4-methyl-1-(4-methylphenylsulfonyl)pyrrolidine at 140K ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first IUC9700029 _journal_volume 53 _journal_year 1997 _chemical_formula_sum 'C32 H42 N2 O5 S2' _chemical_formula_weight 598.80 _chemical_name_systematic ; S~S~-N(1S),2S,3R,4R,5R-N-[(1-Hydroxymethyl)-2-(methylpropyl)]-3- hydroxy-4-methyl-5-(4-methylphenylsulfonimidoylmethyl)-1-(4- methylphenylsulfonyl)-2-(phenylmethyl)-pyrrolidine ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _audit_creation_method SHELXL _cell_angle_alpha 90 _cell_angle_beta 109.8840(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.1376(4) _cell_length_b 11.3443(4) _cell_length_c 13.2368(4) _cell_measurement_reflns_used 6019 _cell_measurement_temperature 140 _cell_measurement_theta_max 25.00 _cell_measurement_theta_min 1.00 _cell_volume 1572.74(9) _computing_cell_refinement 'Siemens SMART' _computing_data_collection 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_molecular_graphics 'XP (Siemens XTL-Plus)' _computing_structure_refinement 'SHELXL-96 (Sheldrick, 1996b)' _computing_structure_solution 'SHELXS-90 (Sheldrick, 1990)' _diffrn_ambient_temperature 140 _diffrn_measurement_device 'Siemens CCD three circle diffractometer' _diffrn_measurement_method \w _diffrn_radiation_monochromator 'highly oriented graphite crystal' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0623 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 12228 _diffrn_reflns_theta_max 26.46 _diffrn_reflns_theta_min 1.64 _diffrn_standards_decay_% 0.0 _diffrn_standards_interval_time 960 _diffrn_standards_number 263 _exptl_absorpt_coefficient_mu 0.211 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8410 _exptl_absorpt_correction_type 'Empirical using SADABS (Sheldrick, 1996a)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.264 _exptl_crystal_description block _exptl_crystal_F_000 640 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.220 _refine_diff_density_min -0.322 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.09(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.055 _refine_ls_goodness_of_fit_obs 1.051 _refine_ls_hydrogen_treatment 'see experimental section' _refine_ls_matrix_type full _refine_ls_number_parameters 374 _refine_ls_number_reflns 5705 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.055 _refine_ls_restrained_S_obs 1.051 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_obs 0.0437 _refine_ls_shift/esd_max 0.016 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.1313P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all 0.0950 _refine_ls_wR_factor_obs 0.0849 _reflns_number_observed 4657 _reflns_number_total 5705 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file qa0019.cif _[local]_cod_data_source_block th1 _[local]_cod_cif_authors_sg_H-M 'P 21' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2006871 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0253(17) 0.0214(16) 0.0246(16) -0.0014(13) 0.0126(13) -0.0012(13) S2 0.0237(4) 0.0194(4) 0.0226(4) -0.0011(3) 0.0093(3) -0.0002(3) O2 0.0276(12) 0.0282(11) 0.0211(11) 0.0004(9) 0.0070(9) 0.0002(9) C21 0.0248(16) 0.0199(17) 0.0260(16) 0.0030(12) 0.0136(13) 0.0038(13) C22 0.0293(17) 0.0257(18) 0.0256(17) 0.0036(14) 0.0108(14) 0.0031(14) C23 0.0269(17) 0.0300(17) 0.0309(17) -0.0019(15) 0.0083(14) 0.0026(16) C24 0.0274(18) 0.0273(17) 0.0361(19) 0.0027(14) 0.0156(15) 0.0113(15) C24' 0.0294(19) 0.040(2) 0.050(2) 0.0017(16) 0.0190(17) 0.0112(18) C25 0.034(2) 0.0357(19) 0.034(2) 0.0025(15) 0.0207(16) -0.0016(15) C26 0.0282(18) 0.0328(19) 0.0275(18) -0.0025(14) 0.0116(14) -0.0053(14) N3 0.0224(14) 0.0192(14) 0.0307(15) -0.0004(10) 0.0109(12) -0.0007(11) C4 0.0218(15) 0.0211(15) 0.0332(17) -0.0025(13) 0.0085(13) -0.0032(15) C5 0.032(2) 0.0254(18) 0.043(2) 0.0027(15) 0.0102(16) 0.0052(16) O5 0.0353(14) 0.0421(16) 0.0322(13) 0.0071(11) 0.0086(11) 0.0099(11) C6 0.0253(18) 0.0295(19) 0.047(2) -0.0026(14) 0.0150(16) -0.0126(16) C61 0.035(2) 0.033(2) 0.055(2) 0.0053(16) 0.0196(18) -0.0033(18) C62 0.0330(19) 0.057(2) 0.0311(19) 0.0055(18) 0.0095(16) -0.0121(19) C11 0.0269(17) 0.0204(16) 0.0219(16) 0.0001(13) 0.0095(13) 0.0023(13) C12 0.0299(18) 0.0217(16) 0.0211(16) -0.0026(13) 0.0063(14) -0.0015(12) C12' 0.047(2) 0.0308(19) 0.0233(17) -0.0068(15) 0.0140(16) -0.0045(14) C13 0.0260(16) 0.0219(17) 0.0261(16) -0.0027(13) 0.0052(13) -0.0023(14) O13 0.0277(12) 0.0272(12) 0.0365(14) -0.0080(10) -0.0014(10) -0.0007(11) C14 0.0207(16) 0.0208(16) 0.0268(17) -0.0005(12) 0.0086(13) 0.0012(13) C41 0.0284(17) 0.0236(16) 0.0296(18) -0.0047(14) 0.0110(14) 0.0013(14) C42 0.0272(16) 0.0286(16) 0.0197(15) -0.0013(15) 0.0101(13) 0.0039(14) C43 0.0318(17) 0.0369(18) 0.0288(17) -0.0061(16) 0.0139(14) 0.0018(16) C44 0.0289(19) 0.061(3) 0.034(2) 0.0026(18) 0.0190(16) 0.0081(18) C45 0.044(2) 0.055(2) 0.0243(19) 0.0141(19) 0.0155(17) -0.0024(17) C46 0.041(2) 0.047(2) 0.0266(18) 0.0045(17) 0.0099(16) -0.0086(16) C47 0.0270(18) 0.041(2) 0.0253(17) 0.0039(15) 0.0092(14) -0.0025(15) N15 0.0241(14) 0.0196(14) 0.0218(13) -0.0014(10) 0.0060(11) 0.0015(10) S51 0.0242(4) 0.0259(4) 0.0231(4) -0.0017(3) 0.0062(3) 0.0013(3) O51 0.0312(13) 0.0264(12) 0.0304(12) -0.0054(10) 0.0041(10) 0.0005(10) O52 0.0325(13) 0.0377(13) 0.0231(12) -0.0003(10) 0.0083(10) 0.0053(9) C51 0.0170(15) 0.0260(17) 0.0270(18) 0.0032(13) 0.0035(13) 0.0030(14) C52 0.0256(18) 0.0268(18) 0.0283(18) -0.0026(13) 0.0061(15) 0.0076(14) C53 0.0256(17) 0.0388(19) 0.0303(18) 0.0028(16) 0.0130(14) 0.0088(16) C54 0.0259(18) 0.0355(19) 0.0246(17) 0.0079(15) 0.0063(14) 0.0044(15) C54' 0.046(2) 0.039(2) 0.043(2) 0.0139(18) 0.0213(19) 0.0087(17) C55 0.0281(19) 0.0262(18) 0.0325(19) 0.0025(14) 0.0060(15) 0.0052(15) C56 0.0228(17) 0.0305(18) 0.0285(18) 0.0011(14) 0.0098(14) 0.0061(14) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol C1 0.3014(3) 0.5760(3) 0.7436(2) 0.0227(7) Uani d . 1 C H1A 0.3562 0.5955 0.8179 0.027 Uiso calc R 1 H H1B 0.2114 0.5860 0.7390 0.027 Uiso calc R 1 H S2 0.33535(7) 0.67813(6) 0.65237(6) 0.02152(17) Uani d . 1 S O2 0.26727(19) 0.63325(18) 0.54391(16) 0.0260(5) Uani d . 1 O C21 0.5015(3) 0.6607(2) 0.6796(2) 0.0223(7) Uani d . 1 C C22 0.5920(3) 0.6964(3) 0.7764(2) 0.0265(7) Uani d . 1 C H22 0.5663 0.7289 0.8320 0.032 Uiso calc R 1 H C23 0.7207(3) 0.6833(3) 0.7900(2) 0.0297(7) Uani d . 1 C H23 0.7832 0.7081 0.8554 0.036 Uiso calc R 1 H C24 0.7603(3) 0.6345(3) 0.7092(3) 0.0290(7) Uani d . 1 C C24' 0.8996(3) 0.6223(3) 0.7226(3) 0.0385(9) Uani d . 1 C H24A 0.9182 0.6689 0.6673 0.058 Uiso calc R 1 H H24B 0.9194 0.5393 0.7154 0.058 Uiso calc R 1 H H24C 0.9518 0.6510 0.7939 0.058 Uiso calc R 1 H C25 0.6665(3) 0.5966(3) 0.6143(3) 0.0324(8) Uani d . 1 C H25 0.6915 0.5608 0.5597 0.039 Uiso calc R 1 H C26 0.5388(3) 0.6105(3) 0.5988(3) 0.0289(7) Uani d . 1 C H26 0.4763 0.5859 0.5334 0.035 Uiso calc R 1 H N3 0.3187(2) 0.8066(2) 0.6793(2) 0.0237(6) Uani d . 1 N C4 0.1855(3) 0.8508(3) 0.6562(2) 0.0256(7) Uani d . 1 C H4 0.1251 0.7826 0.6358 0.031 Uiso calc R 1 H C5 0.1579(3) 0.9340(3) 0.5599(3) 0.0341(8) Uani d . 1 C H5A 0.0715 0.9679 0.5436 0.041 Uiso calc R 1 H H5B 0.2200 0.9997 0.5790 0.041 Uiso calc R 1 H O5 0.1651(2) 0.8762(2) 0.46594(17) 0.0373(6) Uani d . 1 O H5 0.2218 0.8239 0.4841 0.045 Uiso calc R 1 H C6 0.1708(3) 0.9123(3) 0.7545(3) 0.0334(8) Uani d . 1 C H6 0.2275 0.9833 0.7709 0.040 Uiso calc R 1 H C61 0.0321(3) 0.9545(3) 0.7293(3) 0.0402(9) Uani d . 1 C H61A 0.0081 1.0062 0.6663 0.060 Uiso calc R 1 H H61B 0.0251 0.9978 0.7911 0.060 Uiso calc R 1 H H61C -0.0251 0.8861 0.7145 0.060 Uiso calc R 1 H C62 0.2110(3) 0.8331(3) 0.8531(3) 0.0408(9) Uani d . 1 C H62A 0.2011 0.8757 0.9142 0.061 Uiso calc R 1 H H62B 0.3006 0.8101 0.8701 0.061 Uiso calc R 1 H H62C 0.1573 0.7624 0.8386 0.061 Uiso calc R 1 H C11 0.3235(3) 0.4461(3) 0.7207(2) 0.0227(7) Uani d . 1 C H11 0.4050 0.4393 0.7050 0.027 Uiso calc R 1 H C12 0.2147(3) 0.3878(3) 0.6295(2) 0.0248(7) Uani d . 1 C H12 0.1630 0.4495 0.5796 0.030 Uiso calc R 1 H C12' 0.2657(3) 0.2989(3) 0.5670(3) 0.0331(8) Uani d . 1 C H12A 0.3154 0.3405 0.5296 0.050 Uiso calc R 1 H H12B 0.1939 0.2580 0.5144 0.050 Uiso calc R 1 H H12C 0.3204 0.2414 0.6170 0.050 Uiso calc R 1 H C13 0.1350(3) 0.3302(3) 0.6912(2) 0.0256(7) Uani d . 1 C H13 0.0844 0.3922 0.7125 0.031 Uiso calc R 1 H O13 0.0519(2) 0.23902(19) 0.63453(18) 0.0336(5) Uani d . 1 O H13O -0.0202 0.2676 0.6008 0.040 Uiso calc R 1 H C14 0.2346(3) 0.2794(3) 0.7915(2) 0.0226(7) Uani d . 1 C H14 0.2720 0.2072 0.7705 0.027 Uiso calc R 1 H C41 0.1820(3) 0.2459(3) 0.8815(2) 0.0269(7) Uani d . 1 C H41A 0.1211 0.1799 0.8557 0.032 Uiso calc R 1 H H41B 0.2538 0.2168 0.9438 0.032 Uiso calc R 1 H C42 0.1156(3) 0.3438(3) 0.9197(2) 0.0246(6) Uani d . 1 C C43 -0.0168(3) 0.3422(3) 0.8940(2) 0.0316(7) Uani d . 1 C H43 -0.0649 0.2798 0.8514 0.038 Uiso calc R 1 H C44 -0.0797(3) 0.4305(3) 0.9296(3) 0.0389(9) Uani d . 1 C H44 -0.1696 0.4273 0.9125 0.047 Uiso calc R 1 H C45 -0.0104(4) 0.5224(3) 0.9899(3) 0.0402(9) Uani d . 1 C H45 -0.0531 0.5835 1.0133 0.048 Uiso calc R 1 H C46 0.1212(3) 0.5260(3) 1.0164(3) 0.0385(9) Uani d . 1 C H46 0.1686 0.5897 1.0578 0.046 Uiso calc R 1 H C47 0.1838(3) 0.4367(3) 0.9825(2) 0.0312(8) Uani d . 1 C H47 0.2742 0.4388 1.0022 0.037 Uiso calc R 1 H N15 0.3335(2) 0.3747(2) 0.81891(18) 0.0223(6) Uani d . 1 N S51 0.47870(7) 0.34694(7) 0.90178(6) 0.02487(18) Uani d . 1 S O51 0.54993(19) 0.45473(19) 0.90965(16) 0.0309(5) Uani d . 1 O O52 0.4656(2) 0.29491(19) 0.99697(17) 0.0314(5) Uani d . 1 O C51 0.5415(3) 0.2392(3) 0.8378(2) 0.0243(7) Uani d . 1 C C52 0.6109(3) 0.2730(3) 0.7719(2) 0.0277(7) Uani d . 1 C H52 0.6295 0.3537 0.7650 0.033 Uiso calc R 1 H C53 0.6524(3) 0.1865(3) 0.7166(2) 0.0307(7) Uani d . 1 C H53 0.7013 0.2090 0.6733 0.037 Uiso calc R 1 H C54 0.6238(3) 0.0684(3) 0.7234(3) 0.0293(7) Uani d . 1 C C54' 0.6723(3) -0.0255(3) 0.6656(3) 0.0410(9) Uani d . 1 C H54A 0.7080 0.0121 0.6154 0.062 Uiso calc R 1 H H54B 0.6016 -0.0772 0.6258 0.062 Uiso calc R 1 H H54C 0.7387 -0.0721 0.7182 0.062 Uiso calc R 1 H C55 0.5527(3) 0.0364(3) 0.7884(3) 0.0300(8) Uani d . 1 C H55 0.5310 -0.0439 0.7926 0.036 Uiso calc R 1 H C56 0.5137(3) 0.1203(3) 0.8466(2) 0.0270(7) Uani d . 1 C H56 0.4681 0.0972 0.8924 0.032 Uiso calc R 1 H 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 C11 C1 S2 113.5(2) O2 S2 N3 119.75(13) O2 S2 C21 108.46(13) N3 S2 C21 105.08(13) O2 S2 C1 106.02(13) N3 S2 C1 112.76(14) C21 S2 C1 103.55(14) C26 C21 C22 120.8(3) C26 C21 S2 116.9(2) C22 C21 S2 122.3(2) C23 C22 C21 118.7(3) C22 C23 C24 121.4(3) C25 C24 C23 118.2(3) C25 C24 C24' 120.1(3) C23 C24 C24' 121.7(3) C26 C25 C24 121.1(3) C25 C26 C21 119.7(3) C4 N3 S2 117.6(2) N3 C4 C5 106.4(2) N3 C4 C6 111.3(2) C5 C4 C6 112.1(3) O5 C5 C4 112.8(2) C62 C6 C4 112.0(3) C62 C6 C61 110.4(3) C4 C6 C61 110.3(3) N15 C11 C12 104.7(2) N15 C11 C1 108.4(2) C12 C11 C1 115.4(2) C12' C12 C13 113.2(2) C12' C12 C11 111.7(3) C13 C12 C11 102.1(2) O13 C13 C14 109.6(2) O13 C13 C12 114.8(2) C14 C13 C12 104.0(2) N15 C14 C13 101.3(2) N15 C14 C41 115.6(2) C13 C14 C41 114.3(2) C42 C41 C14 115.7(2) C43 C42 C47 118.1(3) C43 C42 C41 120.4(3) C47 C42 C41 121.5(3) C44 C43 C42 121.3(3) C45 C44 C43 119.5(3) C44 C45 C46 120.3(3) C45 C46 C47 120.0(3) C46 C47 C42 120.8(3) C14 N15 C11 110.3(2) C14 N15 S51 119.93(18) C11 N15 S51 116.48(19) O51 S51 O52 120.01(13) O51 S51 N15 106.13(12) O52 S51 N15 106.98(12) O51 S51 C51 108.94(14) O52 S51 C51 108.08(14) N15 S51 C51 105.83(13) C56 C51 C52 120.0(3) C56 C51 S51 119.6(2) C52 C51 S51 120.2(2) C53 C52 C51 119.1(3) C54 C53 C52 121.4(3) C53 C54 C55 118.7(3) C53 C54 C54' 121.2(3) C55 C54 C54' 120.1(3) C56 C55 C54 121.0(3) C55 C56 C51 119.8(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C11 1.541(4) C1 S2 1.804(3) S2 O2 1.468(2) S2 N3 1.526(2) S2 C21 1.771(3) C21 C26 1.394(4) C21 C22 1.394(4) C22 C23 1.391(4) C23 C24 1.402(4) C24 C25 1.401(5) C24 C24' 1.506(4) C25 C26 1.375(4) N3 C4 1.496(4) C4 C5 1.530(4) C4 C6 1.533(4) C5 O5 1.432(4) C6 C62 1.522(5) C6 C61 1.542(4) C11 N15 1.504(4) C11 C12 1.539(4) C12 C12' 1.531(4) C12 C13 1.541(4) C13 O13 1.420(3) C13 C14 1.524(4) C14 N15 1.497(4) C14 C41 1.543(4) C41 C42 1.514(4) C42 C43 1.395(4) C42 C47 1.396(4) C43 C44 1.392(5) C44 C45 1.379(5) C45 C46 1.388(5) C46 C47 1.389(4) N15 S51 1.646(2) S51 O51 1.442(2) S51 O52 1.443(2) S51 C51 1.761(3) C51 C56 1.397(4) C51 C52 1.402(4) C52 C53 1.393(5) C53 C54 1.388(5) C54 C55 1.401(4) C54 C54' 1.514(5) C55 C56 1.384(4) 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 C11 C1 S2 O2 49.7(2) C11 C1 S2 N3 -177.4(2) C11 C1 S2 C21 -64.4(2) O2 S2 C21 C26 0.0(3) N3 S2 C21 C26 -129.1(2) C1 S2 C21 C26 112.4(2) O2 S2 C21 C22 179.3(2) N3 S2 C21 C22 50.2(3) C1 S2 C21 C22 -68.3(3) C26 C21 C22 C23 1.5(4) S2 C21 C22 C23 -177.8(2) C21 C22 C23 C24 -0.6(5) C22 C23 C24 C25 -1.2(5) C22 C23 C24 C24' 178.8(3) C23 C24 C25 C26 2.2(5) C24' C24 C25 C26 -177.8(3) C24 C25 C26 C21 -1.4(5) C22 C21 C26 C25 -0.5(5) S2 C21 C26 C25 178.8(3) O2 S2 N3 C4 53.3(3) C21 S2 N3 C4 175.4(2) C1 S2 N3 C4 -72.5(2) S2 N3 C4 C5 -108.5(2) S2 N3 C4 C6 129.1(2) N3 C4 C5 O5 61.0(3) C6 C4 C5 O5 -177.1(2) N3 C4 C6 C62 -55.3(3) C5 C4 C6 C62 -174.4(3) N3 C4 C6 C61 -178.7(3) C5 C4 C6 C61 62.2(3) S2 C1 C11 N15 162.20(19) S2 C1 C11 C12 -80.9(3) N15 C11 C12 C12' -95.5(3) C1 C11 C12 C12' 145.4(3) N15 C11 C12 C13 25.6(3) C1 C11 C12 C13 -93.4(3) C12' C12 C13 O13 -40.5(4) C11 C12 C13 O13 -160.6(2) C12' C12 C13 C14 79.2(3) C11 C12 C13 C14 -40.9(3) O13 C13 C14 N15 162.6(2) C12 C13 C14 N15 39.5(3) O13 C13 C14 C41 -72.4(3) C12 C13 C14 C41 164.4(2) N15 C14 C41 C42 60.9(3) C13 C14 C41 C42 -56.1(3) C14 C41 C42 C43 108.1(3) C14 C41 C42 C47 -72.8(4) C47 C42 C43 C44 0.0(4) C41 C42 C43 C44 179.1(3) C42 C43 C44 C45 1.2(5) C43 C44 C45 C46 -1.1(5) C44 C45 C46 C47 -0.1(5) C45 C46 C47 C42 1.3(5) C43 C42 C47 C46 -1.2(4) C41 C42 C47 C46 179.7(3) C13 C14 N15 C11 -23.6(3) C41 C14 N15 C11 -147.6(2) C13 C14 N15 S51 -163.21(19) C41 C14 N15 S51 72.7(3) C12 C11 N15 C14 -1.4(3) C1 C11 N15 C14 122.2(3) C12 C11 N15 S51 139.7(2) C1 C11 N15 S51 -96.6(2) C14 N15 S51 O51 179.0(2) C11 N15 S51 O51 41.8(2) C14 N15 S51 O52 -51.7(2) C11 N15 S51 O52 171.00(19) C14 N15 S51 C51 63.4(2) C11 N15 S51 C51 -73.9(2) O51 S51 C51 C56 162.5(2) O52 S51 C51 C56 30.5(3) N15 S51 C51 C56 -83.8(3) O51 S51 C51 C52 -22.3(3) O52 S51 C51 C52 -154.2(2) N15 S51 C51 C52 91.4(3) C56 C51 C52 C53 -0.6(4) S51 C51 C52 C53 -175.8(2) C51 C52 C53 C54 1.6(5) C52 C53 C54 C55 -0.7(5) C52 C53 C54 C54' -178.3(3) C53 C54 C55 C56 -1.3(5) C54' C54 C55 C56 176.4(3) C54 C55 C56 C51 2.2(5) C52 C51 C56 C55 -1.3(5) S51 C51 C56 C55 174.0(2)