# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2008


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        "Peter O'Brien"
_publ_contact_author_email       PAOB1@YORK.AC.UK

_publ_section_title              
;
Stereoselective Aziridination of Cyclic Allylic
Alcohols Using Chloramine-T
;
_publ_author_name                "Peter O'Brien"


  
data_pob0701m 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety 
 'C13 H17 N O3 S' 
_chemical_formula_sum 
 'C13 H17 N O3 S' 
_chemical_formula_weight          267.34 
_chemical_absolute_configuration   ad
  
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            Orthorhombic 
_symmetry_space_group_name_H-M    P2(1)2(1)2(1) 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
  
_cell_length_a                    9.8353(7) 
_cell_length_b                    17.4256(13) 
_cell_length_c                    31.038(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      5319.5(6) 
_cell_formula_units_Z             16 
_cell_measurement_temperature     110(2) 
_cell_measurement_reflns_used     9078 
_cell_measurement_theta_min       2.17 
_cell_measurement_theta_max       25.02 
  
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.28 
_exptl_crystal_size_mid           0.26 
_exptl_crystal_size_min           0.18 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.335 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              2272 
_exptl_absorpt_coefficient_mu     0.243 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.829
_exptl_absorpt_correction_T_max   0.960
_exptl_absorpt_process_details    'SADABS v2.03; (Sheldrick)'
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       110(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             41651 
_diffrn_reflns_av_R_equivalents   0.0470 
_diffrn_reflns_av_sigmaI/netI     0.0383 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -20 
_diffrn_reflns_limit_k_max        20 
_diffrn_reflns_limit_l_min        -36 
_diffrn_reflns_limit_l_max        36 
_diffrn_reflns_theta_min          1.34 
_diffrn_reflns_theta_max          25.06 
_reflns_number_total              9388 
_reflns_number_gt                 8695 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_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^)+(0.0546P)^2^+13.6084P] 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     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0.09(10) 
_refine_ls_number_reflns          9388 
_refine_ls_number_parameters      671 
_refine_ls_number_restraints      4 
_refine_ls_R_factor_all           0.0645 
_refine_ls_R_factor_gt            0.0600 
_refine_ls_wR_factor_ref          0.1647 
_refine_ls_wR_factor_gt           0.1625 
_refine_ls_goodness_of_fit_ref    1.141 
_refine_ls_restrained_S_all       1.140 
_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 
C1 C 0.8124(5) 0.6407(3) 1.05996(15) 0.0241(10) Uani 1 1 d . . . 
H1 H 0.7934 0.6968 1.0632 0.029 Uiso 1 1 calc R . . 
C2 C 0.7328(5) 0.6100(3) 1.02294(16) 0.0260(10) Uani 1 1 d . . . 
H2 H 0.7284 0.6397 0.9954 0.031 Uiso 1 1 calc R . . 
C3 C 0.6129(5) 0.5680(3) 1.03792(18) 0.0290(11) Uani 1 1 d . . . 
C4 C 0.6128(6) 0.5707(3) 1.08686(19) 0.0381(13) Uani 1 1 d . . . 
H4A H 0.5930 0.5193 1.0990 0.046 Uiso 1 1 calc R . . 
H4B H 0.5435 0.6073 1.0975 0.046 Uiso 1 1 calc R . . 
C5 C 0.7560(6) 0.5971(3) 1.09973(18) 0.0362(13) Uani 1 1 d . . . 
H5A H 0.8142 0.5524 1.1067 0.043 Uiso 1 1 calc R . . 
H5B H 0.7521 0.6313 1.1251 0.043 Uiso 1 1 calc R . . 
C6 C 0.4855(6) 0.5566(4) 1.0140(2) 0.0485(16) Uani 1 1 d . . . 
H6A H 0.4174 0.5936 1.0240 0.073 Uiso 1 1 calc R . . 
H6B H 0.4521 0.5043 1.0189 0.073 Uiso 1 1 calc R . . 
H6C H 0.5020 0.5642 0.9832 0.073 Uiso 1 1 calc R . . 
C7 C 1.0681(5) 0.6934(3) 0.98426(14) 0.0229(10) Uani 1 1 d . . . 
C8 C 1.1734(5) 0.6595(3) 0.96100(17) 0.0306(11) Uani 1 1 d . . . 
H8 H 1.2449 0.6338 0.9757 0.037 Uiso 1 1 calc R . . 
C9 C 1.1737(6) 0.6630(3) 0.91700(18) 0.0329(12) Uani 1 1 d . . . 
H9 H 1.2472 0.6408 0.9015 0.040 Uiso 1 1 calc R . . 
C10 C 1.0690(6) 0.6985(3) 0.89433(16) 0.0348(12) Uani 1 1 d . . . 
C11 C 0.9640(6) 0.7320(3) 0.91827(17) 0.0328(12) Uani 1 1 d . . . 
H11 H 0.8910 0.7564 0.9036 0.039 Uiso 1 1 calc R . . 
C12 C 0.9642(5) 0.7305(3) 0.96246(16) 0.0271(11) Uani 1 1 d . . . 
H12 H 0.8933 0.7548 0.9781 0.032 Uiso 1 1 calc R . . 
C13 C 1.0673(8) 0.7006(4) 0.84550(18) 0.0515(17) Uani 1 1 d . . . 
H13A H 1.1564 0.6849 0.8345 0.077 Uiso 1 1 calc R . . 
H13B H 1.0471 0.7529 0.8358 0.077 Uiso 1 1 calc R . . 
H13C H 0.9974 0.6654 0.8347 0.077 Uiso 1 1 calc R . . 
N1 N 0.9589(4) 0.6287(2) 1.05680(13) 0.0255(9) Uani 1 1 d D . . 
H1A H 0.983(6) 0.5810(14) 1.0589(17) 0.031 Uiso 1 1 d D . . 
O1 O 0.7323(4) 0.5275(2) 1.02169(12) 0.0320(8) Uani 1 1 d . . . 
O2 O 1.0226(4) 0.7646(2) 1.05560(11) 0.0333(8) Uani 1 1 d . . . 
O3 O 1.1979(4) 0.6618(2) 1.05398(11) 0.0353(9) Uani 1 1 d . . . 
S1 S 1.06839(12) 0.69079(7) 1.04121(4) 0.0249(3) Uani 1 1 d . . . 
C14 C 0.9664(5) 0.3656(3) 1.04572(15) 0.0247(10) Uani 1 1 d . . . 
H14 H 0.9860 0.3096 1.0424 0.030 Uiso 1 1 calc R . . 
C15 C 1.0357(5) 0.3947(3) 1.08582(16) 0.0259(10) Uani 1 1 d . . . 
H15 H 1.0309 0.3645 1.1132 0.031 Uiso 1 1 calc R . . 
C16 C 1.1604(5) 0.4353(3) 1.07432(17) 0.0271(11) Uani 1 1 d . . . 
C17 C 1.1767(5) 0.4331(3) 1.02626(16) 0.0290(11) Uani 1 1 d . . . 
H17A H 1.2465 0.3950 1.0178 0.035 Uiso 1 1 calc R . . 
H17B H 1.2038 0.4841 1.0151 0.035 Uiso 1 1 calc R . . 
C18 C 1.0359(5) 0.4099(3) 1.00887(16) 0.0311(11) Uani 1 1 d . . . 
H18A H 1.0452 0.3769 0.9831 0.037 Uiso 1 1 calc R . . 
H18B H 0.9823 0.4559 1.0011 0.037 Uiso 1 1 calc R . . 
C19 C 1.2817(6) 0.4459(3) 1.10294(19) 0.0397(14) Uani 1 1 d . . . 
H19A H 1.3174 0.4980 1.0994 0.060 Uiso 1 1 calc R . . 
H19B H 1.3521 0.4086 1.0951 0.060 Uiso 1 1 calc R . . 
H19C H 1.2549 0.4380 1.1330 0.060 Uiso 1 1 calc R . . 
C20 C 0.6987(5) 0.3083(3) 0.97759(15) 0.0224(10) Uani 1 1 d . . . 
C21 C 0.5869(5) 0.3408(3) 0.95686(17) 0.0294(11) Uani 1 1 d . . . 
H21 H 0.5203 0.3681 0.9729 0.035 Uiso 1 1 calc R . . 
C22 C 0.5740(6) 0.3331(3) 0.91357(16) 0.0302(11) Uani 1 1 d . . . 
H22 H 0.4979 0.3555 0.8995 0.036 Uiso 1 1 calc R . . 
C23 C 0.6700(5) 0.2929(3) 0.88906(16) 0.0281(11) Uani 1 1 d . . . 
C24 C 0.7831(6) 0.2634(3) 0.90963(17) 0.0315(12) Uani 1 1 d . . . 
H24 H 0.8517 0.2384 0.8933 0.038 Uiso 1 1 calc R . . 
C25 C 0.7972(5) 0.2699(3) 0.95401(18) 0.0311(12) Uani 1 1 d . . . 
H25 H 0.8739 0.2482 0.9681 0.037 Uiso 1 1 calc R . . 
C26 C 0.6481(7) 0.2812(3) 0.84080(17) 0.0398(14) Uani 1 1 d . . . 
H26A H 0.7285 0.2990 0.8250 0.060 Uiso 1 1 calc R . . 
H26B H 0.5683 0.3106 0.8315 0.060 Uiso 1 1 calc R . . 
H26C H 0.6333 0.2266 0.8349 0.060 Uiso 1 1 calc R . . 
N2 N 0.8200(4) 0.3767(2) 1.04844(14) 0.0261(9) Uani 1 1 d D . . 
H2A H 0.791(5) 0.4205(17) 1.0422(18) 0.031 Uiso 1 1 d D . . 
O4 O 1.0392(3) 0.47758(19) 1.08714(11) 0.0284(8) Uani 1 1 d . . . 
O5 O 0.5816(4) 0.3387(2) 1.04999(11) 0.0353(9) Uani 1 1 d . . . 
O6 O 0.7630(4) 0.2398(2) 1.04861(13) 0.0390(10) Uani 1 1 d . . . 
S2 S 0.71033(12) 0.31254(7) 1.03454(4) 0.0272(3) Uani 1 1 d . . . 
C27 C 0.7252(5) 0.1238(3) 0.29029(16) 0.0299(11) Uani 1 1 d . . . 
H27 H 0.7217 0.0665 0.2896 0.036 Uiso 1 1 calc R . . 
C28 C 0.8440(6) 0.1513(3) 0.26486(17) 0.0316(12) Uani 1 1 d . . . 
H28 H 0.8616 0.1308 0.2353 0.038 Uiso 1 1 calc R . . 
C29 C 0.9581(6) 0.1684(3) 0.29426(16) 0.0320(12) Uani 1 1 d . . . 
C30 C 0.9104(6) 0.1508(4) 0.33930(17) 0.0382(13) Uani 1 1 d . . . 
H30A H 0.9431 0.1902 0.3598 0.046 Uiso 1 1 calc R . . 
H30B H 0.9439 0.0999 0.3488 0.046 Uiso 1 1 calc R . . 
C31 C 0.7572(6) 0.1513(4) 0.33673(17) 0.0394(14) Uani 1 1 d . . . 
H31A H 0.7210 0.2036 0.3417 0.047 Uiso 1 1 calc R . . 
H31B H 0.7173 0.1160 0.3583 0.047 Uiso 1 1 calc R . . 
C32 C 1.1042(6) 0.1669(4) 0.28183(18) 0.0374(13) Uani 1 1 d . . . 
H32A H 1.1121 0.1718 0.2505 0.056 Uiso 1 1 calc R . . 
H32B H 1.1448 0.1182 0.2910 0.056 Uiso 1 1 calc R . . 
H32C H 1.1518 0.2096 0.2958 0.056 Uiso 1 1 calc R . . 
C33 C 0.5804(5) 0.0818(3) 0.19858(16) 0.0290(11) Uani 1 1 d . . . 
C34 C 0.5792(6) 0.1355(3) 0.16592(17) 0.0328(12) Uani 1 1 d . . . 
H34 H 0.5308 0.1823 0.1694 0.039 Uiso 1 1 calc R . . 
C35 C 0.6481(6) 0.1211(3) 0.12841(17) 0.0376(14) Uani 1 1 d . . . 
H35 H 0.6437 0.1570 0.1054 0.045 Uiso 1 1 calc R . . 
C36 C 0.7242(6) 0.0546(3) 0.12361(16) 0.0321(12) Uani 1 1 d . . . 
C37 C 0.7279(6) 0.0017(3) 0.15741(16) 0.0316(12) Uani 1 1 d . . . 
H37 H 0.7803 -0.0438 0.1546 0.038 Uiso 1 1 calc R . . 
C38 C 0.6548(5) 0.0152(3) 0.19542(16) 0.0276(11) Uani 1 1 d . . . 
H38 H 0.6567 -0.0207 0.2184 0.033 Uiso 1 1 calc R . . 
C39 C 0.7967(8) 0.0369(4) 0.08193(18) 0.0467(16) Uani 1 1 d . . . 
H39A H 0.7425 0.0005 0.0651 0.070 Uiso 1 1 calc R . . 
H39B H 0.8858 0.0144 0.0882 0.070 Uiso 1 1 calc R . . 
H39C H 0.8088 0.0843 0.0654 0.070 Uiso 1 1 calc R . . 
N3 N 0.5945(5) 0.1551(2) 0.27630(14) 0.0282(9) Uani 1 1 d D . . 
H3 H 0.613(5) 0.1962(19) 0.2626(15) 0.026(14) Uiso 1 1 d D . . 
O7 O 0.8775(4) 0.2306(2) 0.27556(13) 0.0350(9) Uani 1 1 d . . . 
O8 O 0.4729(4) 0.0323(2) 0.26955(13) 0.0403(10) Uani 1 1 d . . . 
O9 O 0.3805(4) 0.1509(2) 0.23693(14) 0.0424(10) Uani 1 1 d . . . 
S3 S 0.49339(13) 0.10298(7) 0.24716(4) 0.0294(3) Uani 1 1 d . . . 
C40 C 0.2108(5) 0.9002(3) 0.28569(16) 0.0282(11) Uani 1 1 d . . . 
H40 H 0.2084 0.9574 0.2835 0.034 Uiso 1 1 calc R . . 
C41 C 0.3329(5) 0.8709(3) 0.26150(16) 0.0258(10) Uani 1 1 d . . . 
H41 H 0.3531 0.8896 0.2317 0.031 Uiso 1 1 calc R . . 
C42 C 0.4430(5) 0.8548(3) 0.29162(16) 0.0271(11) Uani 1 1 d . . . 
C43 C 0.3954(6) 0.8747(4) 0.33666(17) 0.0379(13) Uani 1 1 d . . . 
H43A H 0.4324 0.9249 0.3460 0.045 Uiso 1 1 calc R . . 
H43B H 0.4232 0.8348 0.3576 0.045 Uiso 1 1 calc R . . 
C44 C 0.2391(6) 0.8781(3) 0.33232(16) 0.0354(13) Uani 1 1 d . . . 
H44A H 0.1983 0.8276 0.3391 0.042 Uiso 1 1 calc R . . 
H44B H 0.2007 0.9168 0.3522 0.042 Uiso 1 1 calc R . . 
C45 C 0.5895(6) 0.8534(3) 0.28104(18) 0.0367(13) Uani 1 1 d . . . 
H45A H 0.6018 0.8343 0.2516 0.055 Uiso 1 1 calc R . . 
H45B H 0.6370 0.8195 0.3012 0.055 Uiso 1 1 calc R . . 
H45C H 0.6268 0.9054 0.2833 0.055 Uiso 1 1 calc R . . 
C46 C 0.0845(5) 0.9399(3) 0.19217(18) 0.0304(12) Uani 1 1 d . . . 
C47 C 0.0884(6) 0.8885(3) 0.1589(2) 0.0396(13) Uani 1 1 d . . . 
H47 H 0.0351 0.8430 0.1601 0.048 Uiso 1 1 calc R . . 
C48 C 0.1709(6) 0.9029(3) 0.12341(19) 0.0392(13) Uani 1 1 d . . . 
H48 H 0.1700 0.8683 0.0998 0.047 Uiso 1 1 calc R . . 
C49 C 0.2538(6) 0.9665(3) 0.12189(17) 0.0341(12) Uani 1 1 d . . . 
C50 C 0.2467(6) 1.0186(3) 0.15597(18) 0.0326(12) Uani 1 1 d . . . 
H50 H 0.3007 1.0638 0.1550 0.039 Uiso 1 1 calc R . . 
C51 C 0.1636(6) 1.0064(3) 0.19102(17) 0.0309(12) Uani 1 1 d . . . 
H51 H 0.1603 1.0424 0.2139 0.037 Uiso 1 1 calc R . . 
C52 C 0.3460(7) 0.9826(4) 0.0848(2) 0.0444(15) Uani 1 1 d . . . 
H52A H 0.3477 0.9382 0.0655 0.067 Uiso 1 1 calc R . . 
H52B H 0.4381 0.9926 0.0956 0.067 Uiso 1 1 calc R . . 
H52C H 0.3130 1.0277 0.0691 0.067 Uiso 1 1 calc R . . 
N4 N 0.0802(5) 0.8695(2) 0.27081(15) 0.0306(10) Uani 1 1 d D . . 
H4 H 0.069(10) 0.824(2) 0.261(3) 0.11(3) Uiso 1 1 d D . . 
O10 O 0.3620(4) 0.79272(19) 0.27352(12) 0.0311(8) Uani 1 1 d . . . 
O11 O -0.1253(4) 0.8714(2) 0.22577(14) 0.0418(10) Uani 1 1 d . . . 
O12 O -0.0415(4) 0.9908(2) 0.25973(14) 0.0409(10) Uani 1 1 d . . . 
S4 S -0.01535(13) 0.91981(7) 0.23856(5) 0.0326(3) Uani 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 
C1 0.024(2) 0.023(2) 0.026(2) 0.000(2) 0.001(2) -0.003(2) 
C2 0.026(2) 0.026(3) 0.026(2) 0.007(2) -0.005(2) 0.003(2) 
C3 0.023(2) 0.022(2) 0.042(3) 0.007(2) -0.006(2) 0.005(2) 
C4 0.033(3) 0.035(3) 0.046(3) 0.012(3) 0.014(3) 0.003(3) 
C5 0.038(3) 0.039(3) 0.032(3) 0.003(2) 0.005(2) -0.002(3) 
C6 0.029(3) 0.041(3) 0.075(5) 0.006(3) -0.010(3) -0.004(3) 
C7 0.030(2) 0.017(2) 0.022(2) 0.0014(19) -0.0005(19) -0.004(2) 
C8 0.032(3) 0.026(2) 0.034(3) -0.005(2) -0.008(2) 0.001(2) 
C9 0.036(3) 0.026(3) 0.037(3) -0.006(2) -0.002(2) 0.009(2) 
C10 0.048(3) 0.033(3) 0.023(3) 0.001(2) -0.003(2) 0.005(3) 
C11 0.038(3) 0.032(3) 0.028(3) 0.008(2) -0.002(2) 0.010(2) 
C12 0.033(3) 0.022(2) 0.026(2) 0.002(2) 0.002(2) 0.001(2) 
C13 0.068(4) 0.059(4) 0.027(3) 0.003(3) -0.005(3) 0.021(4) 
N1 0.030(2) 0.022(2) 0.024(2) 0.0051(17) -0.0061(17) 0.0007(18) 
O1 0.0251(18) 0.0258(18) 0.045(2) -0.0009(16) -0.0051(16) 0.0002(15) 
O2 0.043(2) 0.0285(18) 0.0287(18) -0.0027(15) 0.0000(17) -0.0102(17) 
O3 0.0311(19) 0.050(2) 0.0247(18) 0.0059(17) -0.0064(16) -0.0095(17) 
S1 0.0271(6) 0.0257(6) 0.0221(6) 0.0011(5) -0.0043(5) -0.0075(5) 
C14 0.025(2) 0.021(2) 0.028(3) 0.0023(19) -0.002(2) -0.0030(19) 
C15 0.023(2) 0.023(2) 0.031(3) 0.007(2) -0.004(2) 0.001(2) 
C16 0.022(2) 0.020(2) 0.040(3) -0.002(2) -0.004(2) 0.002(2) 
C17 0.026(3) 0.032(3) 0.029(3) 0.004(2) 0.002(2) -0.006(2) 
C18 0.031(3) 0.036(3) 0.026(2) -0.001(2) 0.003(2) -0.002(2) 
C19 0.036(3) 0.039(3) 0.045(3) 0.005(3) -0.012(3) -0.010(3) 
C20 0.023(2) 0.017(2) 0.027(2) 0.0020(19) 0.0002(19) -0.003(2) 
C21 0.027(3) 0.027(3) 0.033(3) 0.006(2) 0.003(2) 0.005(2) 
C22 0.031(3) 0.032(3) 0.027(3) 0.006(2) 0.000(2) 0.004(2) 
C23 0.032(3) 0.021(2) 0.030(3) -0.001(2) 0.005(2) -0.002(2) 
C24 0.035(3) 0.023(3) 0.036(3) -0.005(2) 0.011(2) 0.000(2) 
C25 0.022(2) 0.025(3) 0.046(3) 0.002(2) -0.004(2) 0.000(2) 
C26 0.056(4) 0.042(3) 0.021(3) 0.001(2) 0.010(2) -0.003(3) 
N2 0.022(2) 0.019(2) 0.037(2) 0.0032(18) -0.0025(18) 0.0009(17) 
O4 0.0296(19) 0.0257(18) 0.0298(18) -0.0012(14) -0.0048(15) 0.0036(15) 
O5 0.0234(18) 0.058(2) 0.0248(18) 0.0048(17) -0.0010(15) -0.0118(17) 
O6 0.049(2) 0.0280(19) 0.040(2) 0.0090(17) -0.0103(18) -0.0147(18) 
S2 0.0244(6) 0.0298(6) 0.0275(6) 0.0068(5) -0.0021(5) -0.0075(5) 
C27 0.034(3) 0.027(3) 0.029(3) 0.000(2) -0.007(2) 0.006(2) 
C28 0.043(3) 0.021(2) 0.030(3) -0.008(2) -0.005(2) 0.008(2) 
C29 0.036(3) 0.036(3) 0.025(2) 0.003(2) -0.004(2) 0.007(2) 
C30 0.043(3) 0.047(3) 0.024(3) -0.004(2) -0.002(2) 0.000(3) 
C31 0.043(3) 0.053(4) 0.022(3) 0.000(3) 0.002(2) 0.003(3) 
C32 0.032(3) 0.048(4) 0.032(3) 0.000(3) -0.008(2) 0.002(3) 
C33 0.027(3) 0.029(3) 0.031(3) 0.000(2) -0.003(2) -0.007(2) 
C34 0.042(3) 0.019(2) 0.037(3) 0.007(2) -0.004(2) -0.006(2) 
C35 0.057(4) 0.029(3) 0.027(3) 0.011(2) -0.008(3) -0.014(3) 
C36 0.041(3) 0.033(3) 0.022(2) -0.003(2) -0.002(2) -0.016(2) 
C37 0.046(3) 0.030(3) 0.019(2) 0.000(2) -0.002(2) -0.003(2) 
C38 0.037(3) 0.026(3) 0.020(2) 0.0005(19) -0.002(2) -0.001(2) 
C39 0.071(4) 0.045(3) 0.024(3) -0.008(3) 0.009(3) -0.020(3) 
N3 0.035(2) 0.020(2) 0.030(2) -0.0003(18) 0.0020(19) 0.0011(19) 
O7 0.036(2) 0.0286(19) 0.040(2) 0.0002(17) -0.0039(17) -0.0026(16) 
O8 0.045(2) 0.0315(19) 0.045(2) -0.0054(17) 0.0138(19) -0.0071(18) 
O9 0.0234(18) 0.039(2) 0.065(3) -0.007(2) -0.0018(19) 0.0031(17) 
S3 0.0270(6) 0.0233(6) 0.0378(7) -0.0010(5) 0.0041(5) -0.0020(5) 
C40 0.032(3) 0.020(2) 0.033(3) -0.003(2) 0.002(2) 0.003(2) 
C41 0.033(3) 0.021(2) 0.024(2) -0.0039(19) -0.001(2) 0.002(2) 
C42 0.034(3) 0.022(2) 0.026(3) 0.004(2) -0.002(2) -0.003(2) 
C43 0.048(3) 0.045(3) 0.021(3) -0.001(2) -0.001(2) -0.008(3) 
C44 0.040(3) 0.044(3) 0.022(3) -0.006(2) 0.006(2) -0.002(3) 
C45 0.037(3) 0.036(3) 0.037(3) 0.003(2) -0.009(2) 0.005(3) 
C46 0.027(3) 0.027(3) 0.038(3) 0.001(2) -0.005(2) 0.007(2) 
C47 0.032(3) 0.032(3) 0.054(4) -0.011(3) -0.005(3) -0.007(2) 
C48 0.045(3) 0.037(3) 0.036(3) -0.014(2) -0.005(3) -0.003(3) 
C49 0.032(3) 0.039(3) 0.031(3) -0.002(2) 0.000(2) 0.001(2) 
C50 0.039(3) 0.026(3) 0.033(3) -0.002(2) -0.005(2) -0.003(2) 
C51 0.037(3) 0.022(3) 0.033(3) -0.004(2) -0.009(2) 0.002(2) 
C52 0.053(4) 0.042(3) 0.038(3) -0.005(3) 0.000(3) -0.008(3) 
N4 0.031(2) 0.022(2) 0.039(2) -0.0012(19) -0.001(2) 0.0013(19) 
O10 0.037(2) 0.0221(18) 0.035(2) -0.0024(15) -0.0026(16) -0.0006(15) 
O11 0.0235(19) 0.038(2) 0.064(3) 0.009(2) 0.0025(18) 0.0026(17) 
O12 0.032(2) 0.036(2) 0.054(3) 0.0057(18) 0.0097(18) 0.0108(17) 
S4 0.0237(6) 0.0271(6) 0.0470(8) 0.0001(6) 0.0023(6) 0.0065(5) 
  
_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 
C1 N1 1.459(6) . ? 
C1 C2 1.490(7) . ? 
C1 C5 1.552(7) . ? 
C1 H1 1.0000 . ? 
C2 O1 1.438(6) . ? 
C2 C3 1.464(7) . ? 
C2 H2 1.0000 . ? 
C3 O1 1.461(6) . ? 
C3 C6 1.470(8) . ? 
C3 C4 1.520(8) . ? 
C4 C5 1.534(8) . ? 
C4 H4A 0.9900 . ? 
C4 H4B 0.9900 . ? 
C5 H5A 0.9900 . ? 
C5 H5B 0.9900 . ? 
C6 H6A 0.9800 . ? 
C6 H6B 0.9800 . ? 
C6 H6C 0.9800 . ? 
C7 C12 1.385(7) . ? 
C7 C8 1.395(7) . ? 
C7 S1 1.768(5) . ? 
C8 C9 1.367(7) . ? 
C8 H8 0.9500 . ? 
C9 C10 1.392(8) . ? 
C9 H9 0.9500 . ? 
C10 C11 1.400(8) . ? 
C10 C13 1.516(7) . ? 
C11 C12 1.372(7) . ? 
C11 H11 0.9500 . ? 
C12 H12 0.9500 . ? 
C13 H13A 0.9800 . ? 
C13 H13B 0.9800 . ? 
C13 H13C 0.9800 . ? 
N1 S1 1.601(4) . ? 
N1 H1A 0.87(2) . ? 
O2 S1 1.434(4) . ? 
O3 S1 1.426(4) . ? 
C14 N2 1.455(6) . ? 
C14 C15 1.507(7) . ? 
C14 C18 1.540(7) . ? 
C14 H14 1.0000 . ? 
C15 O4 1.445(6) . ? 
C15 C16 1.460(7) . ? 
C15 H15 1.0000 . ? 
C16 O4 1.457(6) . ? 
C16 C19 1.499(7) . ? 
C16 C17 1.501(7) . ? 
C17 C18 1.541(7) . ? 
C17 H17A 0.9900 . ? 
C17 H17B 0.9900 . ? 
C18 H18A 0.9900 . ? 
C18 H18B 0.9900 . ? 
C19 H19A 0.9800 . ? 
C19 H19B 0.9800 . ? 
C19 H19C 0.9800 . ? 
C20 C25 1.387(7) . ? 
C20 C21 1.394(7) . ? 
C20 S2 1.773(5) . ? 
C21 C22 1.356(7) . ? 
C21 H21 0.9500 . ? 
C22 C23 1.400(7) . ? 
C22 H22 0.9500 . ? 
C23 C24 1.382(8) . ? 
C23 C26 1.527(7) . ? 
C24 C25 1.389(8) . ? 
C24 H24 0.9500 . ? 
C25 H25 0.9500 . ? 
C26 H26A 0.9800 . ? 
C26 H26B 0.9800 . ? 
C26 H26C 0.9800 . ? 
N2 S2 1.613(4) . ? 
N2 H2A 0.84(2) . ? 
O5 S2 1.429(4) . ? 
O6 S2 1.438(4) . ? 
C27 N3 1.462(7) . ? 
C27 C28 1.489(8) . ? 
C27 C31 1.551(7) . ? 
C27 H27 1.0000 . ? 
C28 O7 1.459(6) . ? 
C28 C29 1.477(7) . ? 
C28 H28 1.0000 . ? 
C29 O7 1.463(6) . ? 
C29 C32 1.488(8) . ? 
C29 C30 1.506(7) . ? 
C30 C31 1.509(8) . ? 
C30 H30A 0.9900 . ? 
C30 H30B 0.9900 . ? 
C31 H31A 0.9900 . ? 
C31 H31B 0.9900 . ? 
C32 H32A 0.9800 . ? 
C32 H32B 0.9800 . ? 
C32 H32C 0.9800 . ? 
C33 C38 1.375(7) . ? 
C33 C34 1.380(7) . ? 
C33 S3 1.773(5) . ? 
C34 C35 1.370(8) . ? 
C34 H34 0.9500 . ? 
C35 C36 1.388(8) . ? 
C35 H35 0.9500 . ? 
C36 C37 1.397(7) . ? 
C36 C39 1.509(8) . ? 
C37 C38 1.401(7) . ? 
C37 H37 0.9500 . ? 
C38 H38 0.9500 . ? 
C39 H39A 0.9800 . ? 
C39 H39B 0.9800 . ? 
C39 H39C 0.9800 . ? 
N3 S3 1.622(4) . ? 
N3 H3 0.85(2) . ? 
O8 S3 1.429(4) . ? 
O9 S3 1.425(4) . ? 
C40 N4 1.465(7) . ? 
C40 C41 1.506(7) . ? 
C40 C44 1.523(7) . ? 
C40 H40 1.0000 . ? 
C41 O10 1.441(6) . ? 
C41 C42 1.457(7) . ? 
C41 H41 1.0000 . ? 
C42 O10 1.456(6) . ? 
C42 C45 1.478(8) . ? 
C42 C43 1.515(7) . ? 
C43 C44 1.544(8) . ? 
C43 H43A 0.9900 . ? 
C43 H43B 0.9900 . ? 
C44 H44A 0.9900 . ? 
C44 H44B 0.9900 . ? 
C45 H45A 0.9800 . ? 
C45 H45B 0.9800 . ? 
C45 H45C 0.9800 . ? 
C46 C47 1.367(8) . ? 
C46 C51 1.396(7) . ? 
C46 S4 1.778(6) . ? 
C47 C48 1.393(9) . ? 
C47 H47 0.9500 . ? 
C48 C49 1.375(8) . ? 
C48 H48 0.9500 . ? 
C49 C50 1.397(8) . ? 
C49 C52 1.492(8) . ? 
C50 C51 1.377(8) . ? 
C50 H50 0.9500 . ? 
C51 H51 0.9500 . ? 
C52 H52A 0.9800 . ? 
C52 H52B 0.9800 . ? 
C52 H52C 0.9800 . ? 
N4 S4 1.629(5) . ? 
N4 H4 0.86(2) . ? 
O11 S4 1.428(4) . ? 
O12 S4 1.424(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 
 _geom_angle_publ_flag 
N1 C1 C2 114.6(4) . . ? 
N1 C1 C5 109.7(4) . . ? 
C2 C1 C5 104.5(4) . . ? 
N1 C1 H1 109.3 . . ? 
C2 C1 H1 109.3 . . ? 
C5 C1 H1 109.3 . . ? 
O1 C2 C3 60.4(3) . . ? 
O1 C2 C1 112.4(4) . . ? 
C3 C2 C1 111.0(4) . . ? 
O1 C2 H2 119.7 . . ? 
C3 C2 H2 119.7 . . ? 
C1 C2 H2 119.7 . . ? 
O1 C3 C2 58.9(3) . . ? 
O1 C3 C6 116.5(5) . . ? 
C2 C3 C6 126.5(5) . . ? 
O1 C3 C4 111.1(4) . . ? 
C2 C3 C4 107.6(4) . . ? 
C6 C3 C4 120.6(5) . . ? 
C3 C4 C5 105.6(4) . . ? 
C3 C4 H4A 110.6 . . ? 
C5 C4 H4A 110.6 . . ? 
C3 C4 H4B 110.6 . . ? 
C5 C4 H4B 110.6 . . ? 
H4A C4 H4B 108.7 . . ? 
C4 C5 C1 105.5(4) . . ? 
C4 C5 H5A 110.6 . . ? 
C1 C5 H5A 110.6 . . ? 
C4 C5 H5B 110.6 . . ? 
C1 C5 H5B 110.6 . . ? 
H5A C5 H5B 108.8 . . ? 
C3 C6 H6A 109.5 . . ? 
C3 C6 H6B 109.5 . . ? 
H6A C6 H6B 109.5 . . ? 
C3 C6 H6C 109.5 . . ? 
H6A C6 H6C 109.5 . . ? 
H6B C6 H6C 109.5 . . ? 
C12 C7 C8 119.5(4) . . ? 
C12 C7 S1 120.1(4) . . ? 
C8 C7 S1 120.3(4) . . ? 
C9 C8 C7 120.0(5) . . ? 
C9 C8 H8 120.0 . . ? 
C7 C8 H8 120.0 . . ? 
C8 C9 C10 121.6(5) . . ? 
C8 C9 H9 119.2 . . ? 
C10 C9 H9 119.2 . . ? 
C9 C10 C11 117.6(5) . . ? 
C9 C10 C13 121.6(5) . . ? 
C11 C10 C13 120.8(5) . . ? 
C12 C11 C10 121.4(5) . . ? 
C12 C11 H11 119.3 . . ? 
C10 C11 H11 119.3 . . ? 
C11 C12 C7 119.9(5) . . ? 
C11 C12 H12 120.0 . . ? 
C7 C12 H12 120.0 . . ? 
C10 C13 H13A 109.5 . . ? 
C10 C13 H13B 109.5 . . ? 
H13A C13 H13B 109.5 . . ? 
C10 C13 H13C 109.5 . . ? 
H13A C13 H13C 109.5 . . ? 
H13B C13 H13C 109.5 . . ? 
C1 N1 S1 126.0(3) . . ? 
C1 N1 H1A 113(4) . . ? 
S1 N1 H1A 119(4) . . ? 
C2 O1 C3 60.6(3) . . ? 
O3 S1 O2 120.8(2) . . ? 
O3 S1 N1 106.1(2) . . ? 
O2 S1 N1 107.5(2) . . ? 
O3 S1 C7 106.8(2) . . ? 
O2 S1 C7 106.7(2) . . ? 
N1 S1 C7 108.6(2) . . ? 
N2 C14 C15 110.8(4) . . ? 
N2 C14 C18 114.5(4) . . ? 
C15 C14 C18 104.1(4) . . ? 
N2 C14 H14 109.1 . . ? 
C15 C14 H14 109.1 . . ? 
C18 C14 H14 109.1 . . ? 
O4 C15 C16 60.2(3) . . ? 
O4 C15 C14 111.8(4) . . ? 
C16 C15 C14 109.9(4) . . ? 
O4 C15 H15 120.2 . . ? 
C16 C15 H15 120.2 . . ? 
C14 C15 H15 120.2 . . ? 
O4 C16 C15 59.4(3) . . ? 
O4 C16 C19 115.3(4) . . ? 
C15 C16 C19 125.7(5) . . ? 
O4 C16 C17 111.8(4) . . ? 
C15 C16 C17 108.7(4) . . ? 
C19 C16 C17 120.5(5) . . ? 
C16 C17 C18 105.0(4) . . ? 
C16 C17 H17A 110.8 . . ? 
C18 C17 H17A 110.7 . . ? 
C16 C17 H17B 110.8 . . ? 
C18 C17 H17B 110.7 . . ? 
H17A C17 H17B 108.8 . . ? 
C17 C18 C14 105.7(4) . . ? 
C17 C18 H18A 110.6 . . ? 
C14 C18 H18A 110.6 . . ? 
C17 C18 H18B 110.6 . . ? 
C14 C18 H18B 110.6 . . ? 
H18A C18 H18B 108.7 . . ? 
C16 C19 H19A 109.5 . . ? 
C16 C19 H19B 109.5 . . ? 
H19A C19 H19B 109.5 . . ? 
C16 C19 H19C 109.5 . . ? 
H19A C19 H19C 109.5 . . ? 
H19B C19 H19C 109.5 . . ? 
C25 C20 C21 120.2(5) . . ? 
C25 C20 S2 120.1(4) . . ? 
C21 C20 S2 119.6(4) . . ? 
C22 C21 C20 119.4(5) . . ? 
C22 C21 H21 120.3 . . ? 
C20 C21 H21 120.3 . . ? 
C21 C22 C23 121.7(5) . . ? 
C21 C22 H22 119.2 . . ? 
C23 C22 H22 119.2 . . ? 
C24 C23 C22 118.5(5) . . ? 
C24 C23 C26 121.2(5) . . ? 
C22 C23 C26 120.3(5) . . ? 
C23 C24 C25 120.5(5) . . ? 
C23 C24 H24 119.7 . . ? 
C25 C24 H24 119.7 . . ? 
C20 C25 C24 119.5(5) . . ? 
C20 C25 H25 120.2 . . ? 
C24 C25 H25 120.2 . . ? 
C23 C26 H26A 109.5 . . ? 
C23 C26 H26B 109.5 . . ? 
H26A C26 H26B 109.5 . . ? 
C23 C26 H26C 109.5 . . ? 
H26A C26 H26C 109.5 . . ? 
H26B C26 H26C 109.5 . . ? 
C14 N2 S2 123.6(3) . . ? 
C14 N2 H2A 117(4) . . ? 
S2 N2 H2A 110(4) . . ? 
C15 O4 C16 60.4(3) . . ? 
O5 S2 O6 119.9(2) . . ? 
O5 S2 N2 106.3(2) . . ? 
O6 S2 N2 106.8(2) . . ? 
O5 S2 C20 106.9(2) . . ? 
O6 S2 C20 106.8(2) . . ? 
N2 S2 C20 109.8(2) . . ? 
N3 C27 C28 114.4(4) . . ? 
N3 C27 C31 109.8(4) . . ? 
C28 C27 C31 103.5(4) . . ? 
N3 C27 H27 109.6 . . ? 
C28 C27 H27 109.6 . . ? 
C31 C27 H27 109.6 . . ? 
O7 C28 C29 59.8(3) . . ? 
O7 C28 C27 111.1(4) . . ? 
C29 C28 C27 109.5(4) . . ? 
O7 C28 H28 120.5 . . ? 
C29 C28 H28 120.5 . . ? 
C27 C28 H28 120.5 . . ? 
O7 C29 C28 59.5(3) . . ? 
O7 C29 C32 115.7(5) . . ? 
C28 C29 C32 124.7(5) . . ? 
O7 C29 C30 110.5(4) . . ? 
C28 C29 C30 107.2(5) . . ? 
C32 C29 C30 122.5(5) . . ? 
C29 C30 C31 105.1(4) . . ? 
C29 C30 H30A 110.7 . . ? 
C31 C30 H30A 110.7 . . ? 
C29 C30 H30B 110.7 . . ? 
C31 C30 H30B 110.7 . . ? 
H30A C30 H30B 108.8 . . ? 
C30 C31 C27 104.5(4) . . ? 
C30 C31 H31A 110.9 . . ? 
C27 C31 H31A 110.9 . . ? 
C30 C31 H31B 110.9 . . ? 
C27 C31 H31B 110.9 . . ? 
H31A C31 H31B 108.9 . . ? 
C29 C32 H32A 109.5 . . ? 
C29 C32 H32B 109.5 . . ? 
H32A C32 H32B 109.5 . . ? 
C29 C32 H32C 109.5 . . ? 
H32A C32 H32C 109.5 . . ? 
H32B C32 H32C 109.5 . . ? 
C38 C33 C34 121.6(5) . . ? 
C38 C33 S3 119.6(4) . . ? 
C34 C33 S3 118.6(4) . . ? 
C35 C34 C33 119.7(5) . . ? 
C35 C34 H34 120.1 . . ? 
C33 C34 H34 120.1 . . ? 
C34 C35 C36 120.7(5) . . ? 
C34 C35 H35 119.6 . . ? 
C36 C35 H35 119.6 . . ? 
C35 C36 C37 119.0(5) . . ? 
C35 C36 C39 121.1(5) . . ? 
C37 C36 C39 119.8(5) . . ? 
C36 C37 C38 120.5(5) . . ? 
C36 C37 H37 119.7 . . ? 
C38 C37 H37 119.7 . . ? 
C33 C38 C37 118.4(5) . . ? 
C33 C38 H38 120.8 . . ? 
C37 C38 H38 120.8 . . ? 
C36 C39 H39A 109.5 . . ? 
C36 C39 H39B 109.5 . . ? 
H39A C39 H39B 109.5 . . ? 
C36 C39 H39C 109.5 . . ? 
H39A C39 H39C 109.5 . . ? 
H39B C39 H39C 109.5 . . ? 
C27 N3 S3 119.8(3) . . ? 
C27 N3 H3 106(4) . . ? 
S3 N3 H3 109(4) . . ? 
C28 O7 C29 60.7(3) . . ? 
O9 S3 O8 120.2(3) . . ? 
O9 S3 N3 105.9(2) . . ? 
O8 S3 N3 107.3(2) . . ? 
O9 S3 C33 108.0(3) . . ? 
O8 S3 C33 107.6(2) . . ? 
N3 S3 C33 107.2(2) . . ? 
N4 C40 C41 114.8(4) . . ? 
N4 C40 C44 111.6(4) . . ? 
C41 C40 C44 104.0(4) . . ? 
N4 C40 H40 108.8 . . ? 
C41 C40 H40 108.8 . . ? 
C44 C40 H40 108.8 . . ? 
O10 C41 C42 60.3(3) . . ? 
O10 C41 C40 110.5(4) . . ? 
C42 C41 C40 109.8(4) . . ? 
O10 C41 H41 120.6 . . ? 
C42 C41 H41 120.6 . . ? 
C40 C41 H41 120.6 . . ? 
O10 C42 C41 59.3(3) . . ? 
O10 C42 C45 115.8(5) . . ? 
C41 C42 C45 125.8(5) . . ? 
O10 C42 C43 110.9(4) . . ? 
C41 C42 C43 108.6(4) . . ? 
C45 C42 C43 120.7(5) . . ? 
C42 C43 C44 103.6(4) . . ? 
C42 C43 H43A 111.0 . . ? 
C44 C43 H43A 111.0 . . ? 
C42 C43 H43B 111.0 . . ? 
C44 C43 H43B 111.0 . . ? 
H43A C43 H43B 109.0 . . ? 
C40 C44 C43 105.9(4) . . ? 
C40 C44 H44A 110.5 . . ? 
C43 C44 H44A 110.5 . . ? 
C40 C44 H44B 110.5 . . ? 
C43 C44 H44B 110.5 . . ? 
H44A C44 H44B 108.7 . . ? 
C42 C45 H45A 109.5 . . ? 
C42 C45 H45B 109.5 . . ? 
H45A C45 H45B 109.5 . . ? 
C42 C45 H45C 109.5 . . ? 
H45A C45 H45C 109.5 . . ? 
H45B C45 H45C 109.5 . . ? 
C47 C46 C51 120.6(5) . . ? 
C47 C46 S4 119.8(4) . . ? 
C51 C46 S4 119.5(4) . . ? 
C46 C47 C48 119.7(5) . . ? 
C46 C47 H47 120.2 . . ? 
C48 C47 H47 120.2 . . ? 
C49 C48 C47 121.2(5) . . ? 
C49 C48 H48 119.4 . . ? 
C47 C48 H48 119.4 . . ? 
C48 C49 C50 117.9(5) . . ? 
C48 C49 C52 122.6(5) . . ? 
C50 C49 C52 119.4(5) . . ? 
C51 C50 C49 121.8(5) . . ? 
C51 C50 H50 119.1 . . ? 
C49 C50 H50 119.1 . . ? 
C50 C51 C46 118.7(5) . . ? 
C50 C51 H51 120.7 . . ? 
C46 C51 H51 120.7 . . ? 
C49 C52 H52A 109.5 . . ? 
C49 C52 H52B 109.5 . . ? 
H52A C52 H52B 109.5 . . ? 
C49 C52 H52C 109.5 . . ? 
H52A C52 H52C 109.5 . . ? 
H52B C52 H52C 109.5 . . ? 
C40 N4 S4 120.2(3) . . ? 
C40 N4 H4 124(7) . . ? 
S4 N4 H4 102(7) . . ? 
C41 O10 C42 60.4(3) . . ? 
O12 S4 O11 120.3(2) . . ? 
O12 S4 N4 106.7(2) . . ? 
O11 S4 N4 106.9(2) . . ? 
O12 S4 C46 107.6(2) . . ? 
O11 S4 C46 108.0(3) . . ? 
N4 S4 C46 106.6(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 
N1 C1 C2 O1 69.1(5) . . . . ? 
C5 C1 C2 O1 -50.9(5) . . . . ? 
N1 C1 C2 C3 134.7(4) . . . . ? 
C5 C1 C2 C3 14.7(5) . . . . ? 
C1 C2 C3 O1 -104.6(4) . . . . ? 
O1 C2 C3 C6 -101.7(6) . . . . ? 
C1 C2 C3 C6 153.7(5) . . . . ? 
O1 C2 C3 C4 104.5(4) . . . . ? 
C1 C2 C3 C4 -0.2(6) . . . . ? 
O1 C3 C4 C5 48.1(6) . . . . ? 
C2 C3 C4 C5 -14.7(6) . . . . ? 
C6 C3 C4 C5 -170.4(5) . . . . ? 
C3 C4 C5 C1 23.3(6) . . . . ? 
N1 C1 C5 C4 -146.4(4) . . . . ? 
C2 C1 C5 C4 -23.2(5) . . . . ? 
C12 C7 C8 C9 0.2(8) . . . . ? 
S1 C7 C8 C9 -178.8(4) . . . . ? 
C7 C8 C9 C10 -1.6(8) . . . . ? 
C8 C9 C10 C11 1.4(8) . . . . ? 
C8 C9 C10 C13 -178.3(6) . . . . ? 
C9 C10 C11 C12 0.3(8) . . . . ? 
C13 C10 C11 C12 180.0(6) . . . . ? 
C10 C11 C12 C7 -1.7(8) . . . . ? 
C8 C7 C12 C11 1.5(7) . . . . ? 
S1 C7 C12 C11 -179.6(4) . . . . ? 
C2 C1 N1 S1 99.3(5) . . . . ? 
C5 C1 N1 S1 -143.7(4) . . . . ? 
C1 C2 O1 C3 102.2(5) . . . . ? 
C6 C3 O1 C2 118.4(5) . . . . ? 
C4 C3 O1 C2 -98.4(5) . . . . ? 
C1 N1 S1 O3 165.0(4) . . . . ? 
C1 N1 S1 O2 34.5(5) . . . . ? 
C1 N1 S1 C7 -80.6(4) . . . . ? 
C12 C7 S1 O3 -169.6(4) . . . . ? 
C8 C7 S1 O3 9.3(5) . . . . ? 
C12 C7 S1 O2 -39.2(4) . . . . ? 
C8 C7 S1 O2 139.7(4) . . . . ? 
C12 C7 S1 N1 76.4(4) . . . . ? 
C8 C7 S1 N1 -104.7(4) . . . . ? 
N2 C14 C15 O4 -73.7(5) . . . . ? 
C18 C14 C15 O4 49.8(5) . . . . ? 
N2 C14 C15 C16 -138.6(4) . . . . ? 
C18 C14 C15 C16 -15.0(5) . . . . ? 
C14 C15 C16 O4 104.3(4) . . . . ? 
O4 C15 C16 C19 100.7(6) . . . . ? 
C14 C15 C16 C19 -155.0(5) . . . . ? 
O4 C15 C16 C17 -104.8(4) . . . . ? 
C14 C15 C16 C17 -0.6(6) . . . . ? 
O4 C16 C17 C18 -47.7(5) . . . . ? 
C15 C16 C17 C18 16.0(6) . . . . ? 
C19 C16 C17 C18 172.0(5) . . . . ? 
C16 C17 C18 C14 -25.0(5) . . . . ? 
N2 C14 C18 C17 145.5(4) . . . . ? 
C15 C14 C18 C17 24.4(5) . . . . ? 
C25 C20 C21 C22 1.4(7) . . . . ? 
S2 C20 C21 C22 -175.7(4) . . . . ? 
C20 C21 C22 C23 0.3(8) . . . . ? 
C21 C22 C23 C24 -2.7(8) . . . . ? 
C21 C22 C23 C26 176.3(5) . . . . ? 
C22 C23 C24 C25 3.4(7) . . . . ? 
C26 C23 C24 C25 -175.6(5) . . . . ? 
C21 C20 C25 C24 -0.6(7) . . . . ? 
S2 C20 C25 C24 176.5(4) . . . . ? 
C23 C24 C25 C20 -1.8(8) . . . . ? 
C15 C14 N2 S2 -136.1(4) . . . . ? 
C18 C14 N2 S2 106.6(4) . . . . ? 
C14 C15 O4 C16 -101.2(5) . . . . ? 
C19 C16 O4 C15 -118.1(5) . . . . ? 
C17 C16 O4 C15 99.5(5) . . . . ? 
C14 N2 S2 O5 168.5(4) . . . . ? 
C14 N2 S2 O6 39.3(5) . . . . ? 
C14 N2 S2 C20 -76.2(4) . . . . ? 
C25 C20 S2 O5 -166.5(4) . . . . ? 
C21 C20 S2 O5 10.6(5) . . . . ? 
C25 C20 S2 O6 -36.9(5) . . . . ? 
C21 C20 S2 O6 140.2(4) . . . . ? 
C25 C20 S2 N2 78.6(4) . . . . ? 
C21 C20 S2 N2 -104.3(4) . . . . ? 
N3 C27 C28 O7 73.9(5) . . . . ? 
C31 C27 C28 O7 -45.6(5) . . . . ? 
N3 C27 C28 C29 138.1(4) . . . . ? 
C31 C27 C28 C29 18.5(6) . . . . ? 
C27 C28 C29 O7 -103.7(5) . . . . ? 
O7 C28 C29 C32 -101.8(6) . . . . ? 
C27 C28 C29 C32 154.6(5) . . . . ? 
O7 C28 C29 C30 104.1(5) . . . . ? 
C27 C28 C29 C30 0.4(6) . . . . ? 
O7 C29 C30 C31 43.3(6) . . . . ? 
C28 C29 C30 C31 -19.9(6) . . . . ? 
C32 C29 C30 C31 -174.7(5) . . . . ? 
C29 C30 C31 C27 31.0(6) . . . . ? 
N3 C27 C31 C30 -153.0(5) . . . . ? 
C28 C27 C31 C30 -30.4(6) . . . . ? 
C38 C33 C34 C35 3.3(8) . . . . ? 
S3 C33 C34 C35 178.7(4) . . . . ? 
C33 C34 C35 C36 -2.9(8) . . . . ? 
C34 C35 C36 C37 1.0(8) . . . . ? 
C34 C35 C36 C39 178.0(5) . . . . ? 
C35 C36 C37 C38 0.6(8) . . . . ? 
C39 C36 C37 C38 -176.4(5) . . . . ? 
C34 C33 C38 C37 -1.6(8) . . . . ? 
S3 C33 C38 C37 -177.0(4) . . . . ? 
C36 C37 C38 C33 -0.3(8) . . . . ? 
C28 C27 N3 S3 101.7(5) . . . . ? 
C31 C27 N3 S3 -142.4(4) . . . . ? 
C27 C28 O7 C29 100.9(5) . . . . ? 
C32 C29 O7 C28 116.8(5) . . . . ? 
C30 C29 O7 C28 -98.4(5) . . . . ? 
C27 N3 S3 O9 -176.6(4) . . . . ? 
C27 N3 S3 O8 53.8(4) . . . . ? 
C27 N3 S3 C33 -61.5(4) . . . . ? 
C38 C33 S3 O9 -153.6(4) . . . . ? 
C34 C33 S3 O9 30.9(5) . . . . ? 
C38 C33 S3 O8 -22.4(5) . . . . ? 
C34 C33 S3 O8 162.1(4) . . . . ? 
C38 C33 S3 N3 92.8(4) . . . . ? 
C34 C33 S3 N3 -82.7(5) . . . . ? 
N4 C40 C41 O10 -73.9(5) . . . . ? 
C44 C40 C41 O10 48.2(5) . . . . ? 
N4 C40 C41 C42 -138.6(4) . . . . ? 
C44 C40 C41 C42 -16.4(5) . . . . ? 
C40 C41 C42 O10 102.9(4) . . . . ? 
O10 C41 C42 C45 101.3(6) . . . . ? 
C40 C41 C42 C45 -155.9(5) . . . . ? 
O10 C41 C42 C43 -103.8(4) . . . . ? 
C40 C41 C42 C43 -1.0(6) . . . . ? 
O10 C42 C43 C44 -45.7(6) . . . . ? 
C41 C42 C43 C44 17.7(6) . . . . ? 
C45 C42 C43 C44 174.1(5) . . . . ? 
N4 C40 C44 C43 151.4(4) . . . . ? 
C41 C40 C44 C43 27.1(6) . . . . ? 
C42 C43 C44 C40 -27.7(6) . . . . ? 
C51 C46 C47 C48 -0.8(9) . . . . ? 
S4 C46 C47 C48 -177.4(4) . . . . ? 
C46 C47 C48 C49 3.1(9) . . . . ? 
C47 C48 C49 C50 -3.8(9) . . . . ? 
C47 C48 C49 C52 178.4(6) . . . . ? 
C48 C49 C50 C51 2.3(8) . . . . ? 
C52 C49 C50 C51 -179.8(5) . . . . ? 
C49 C50 C51 C46 -0.1(8) . . . . ? 
C47 C46 C51 C50 -0.6(8) . . . . ? 
S4 C46 C51 C50 176.0(4) . . . . ? 
C41 C40 N4 S4 -99.2(5) . . . . ? 
C44 C40 N4 S4 142.8(4) . . . . ? 
C40 C41 O10 C42 -101.7(4) . . . . ? 
C45 C42 O10 C41 -117.9(5) . . . . ? 
C43 C42 O10 C41 99.8(5) . . . . ? 
C40 N4 S4 O12 -57.2(4) . . . . ? 
C40 N4 S4 O11 172.9(4) . . . . ? 
C40 N4 S4 C46 57.6(4) . . . . ? 
C47 C46 S4 O12 -159.1(4) . . . . ? 
C51 C46 S4 O12 24.2(5) . . . . ? 
C47 C46 S4 O11 -27.8(5) . . . . ? 
C51 C46 S4 O11 155.5(4) . . . . ? 
C47 C46 S4 N4 86.7(5) . . . . ? 
C51 C46 S4 N4 -90.0(4) . . . . ? 
  
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
N4 H4 O7  0.86(2) 2.05(5) 2.847(6) 153(9) 3_655 
N3 H3 O10  0.85(2) 2.04(2) 2.886(6) 174(5) 3_645 
N2 H2A O1  0.84(2) 2.05(2) 2.886(5) 174(6) . 
N1 H1A O4  0.87(2) 2.08(3) 2.906(5) 159(5) . 
  
_diffrn_measured_fraction_theta_max    0.995 
_diffrn_reflns_theta_full              25.06 
_diffrn_measured_fraction_theta_full   0.995 
_refine_diff_density_max    0.495 
_refine_diff_density_min   -0.366 
_refine_diff_density_rms    0.084 



data_pob0503a
_database_code_depnum_ccdc_archive 'CCDC 692183'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H27 N O3 S'
_chemical_formula_sum            'C18 H27 N O3 S'
_chemical_formula_weight         337.47
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   P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   12.940(3)
_cell_length_b                   12.042(2)
_cell_length_c                   11.540(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.062(4)
_cell_angle_gamma                90.00
_cell_volume                     1795.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3998
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.48
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728

_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.487
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'SADABS v2.03; (Sheldrick)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11428
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0603
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4098
_reflns_number_gt                3325
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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 Rfactors
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^)+(0.0677P)^2^+0.3592P] 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         4098
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.1160
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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

C1 C 0.75619(12) 0.04469(13) 0.06764(14) 0.0177(3) Uani 1 1 d . . .
C2 C 0.73979(12) 0.16744(13) 0.05328(14) 0.0180(3) Uani 1 1 d . . .
H2 H 0.7288 0.2089 0.1267 0.022 Uiso 1 1 calc R . .
C3 C 0.68930(13) 0.21888(13) -0.05572(15) 0.0200(3) Uani 1 1 d . . .
C4 C 0.68542(14) 0.13641(14) -0.15695(15) 0.0228(4) Uani 1 1 d . . .
H4A H 0.6376 0.1649 -0.2198 0.027 Uiso 1 1 calc R . .
H4B H 0.7551 0.1305 -0.1879 0.027 Uiso 1 1 calc R . .
C5 C 0.64959(13) 0.02091(14) -0.12096(15) 0.0231(4) Uani 1 1 d . . .
H5A H 0.5823 0.0269 -0.0845 0.028 Uiso 1 1 calc R . .
H5B H 0.6399 -0.0269 -0.1905 0.028 Uiso 1 1 calc R . .
C6 C 0.72958(13) -0.03144(13) -0.03535(15) 0.0218(4) Uani 1 1 d . . .
H6A H 0.7021 -0.1025 -0.0067 0.026 Uiso 1 1 calc R . .
H6B H 0.7933 -0.0479 -0.0759 0.026 Uiso 1 1 calc R . .
C7 C 0.74407(13) -0.00480(13) 0.18721(15) 0.0207(3) Uani 1 1 d . . .
H7A H 0.7752 0.0457 0.2471 0.025 Uiso 1 1 calc R . .
H7B H 0.7810 -0.0767 0.1933 0.025 Uiso 1 1 calc R . .
C8 C 0.62950(13) -0.02251(14) 0.20865(16) 0.0252(4) Uani 1 1 d . . .
H8A H 0.5933 0.0498 0.2021 0.030 Uiso 1 1 calc R . .
H8B H 0.5988 -0.0718 0.1474 0.030 Uiso 1 1 calc R . .
C9 C 0.61093(14) -0.07311(15) 0.32699(17) 0.0291(4) Uani 1 1 d . . .
H9A H 0.6487 -0.0286 0.3877 0.035 Uiso 1 1 calc R . .
H9B H 0.5362 -0.0681 0.3408 0.035 Uiso 1 1 calc R . .
C10 C 0.64469(17) -0.19362(17) 0.3393(2) 0.0397(5) Uani 1 1 d . . .
H10A H 0.6066 -0.2388 0.2807 0.060 Uiso 1 1 calc R . .
H10B H 0.6302 -0.2205 0.4169 0.060 Uiso 1 1 calc R . .
H10C H 0.7191 -0.1993 0.3282 0.060 Uiso 1 1 calc R . .
C11 C 0.58177(14) 0.25923(16) -0.02791(16) 0.0276(4) Uani 1 1 d . . .
H11A H 0.5879 0.3153 0.0337 0.041 Uiso 1 1 calc R . .
H11B H 0.5408 0.1964 -0.0019 0.041 Uiso 1 1 calc R . .
H11C H 0.5475 0.2920 -0.0976 0.041 Uiso 1 1 calc R . .
C12 C 1.01283(12) 0.24289(12) 0.07025(14) 0.0178(3) Uani 1 1 d . . .
C13 C 1.05423(12) 0.20885(13) -0.03310(14) 0.0199(3) Uani 1 1 d . . .
H13 H 1.0408 0.1365 -0.0630 0.024 Uiso 1 1 calc R . .
C14 C 1.11524(13) 0.28232(14) -0.09128(15) 0.0216(3) Uani 1 1 d . . .
H14 H 1.1436 0.2598 -0.1618 0.026 Uiso 1 1 calc R . .
C15 C 1.13592(13) 0.38907(14) -0.04845(15) 0.0217(3) Uani 1 1 d . . .
C16 C 1.09368(13) 0.42076(13) 0.05516(15) 0.0225(4) Uani 1 1 d . . .
H16 H 1.1075 0.4930 0.0854 0.027 Uiso 1 1 calc R . .
C17 C 1.03191(13) 0.34889(13) 0.11493(15) 0.0204(3) Uani 1 1 d . . .
H17 H 1.0031 0.3715 0.1852 0.024 Uiso 1 1 calc R . .
C18 C 1.20064(15) 0.46787(16) -0.11554(17) 0.0299(4) Uani 1 1 d . . .
H18A H 1.2076 0.5386 -0.0738 0.045 Uiso 1 1 calc R . .
H18B H 1.1671 0.4807 -0.1925 0.045 Uiso 1 1 calc R . .
H18C H 1.2693 0.4356 -0.1240 0.045 Uiso 1 1 calc R . .
N1 N 0.84502(10) 0.12070(11) 0.04391(12) 0.0175(3) Uani 1 1 d . . .
O1 O 0.74553(9) 0.31656(9) -0.08526(10) 0.0237(3) Uani 1 1 d . . .
H1 H 0.8070 0.2994 -0.0970 0.036 Uiso 1 1 calc R . .
O2 O 0.99256(9) 0.04763(9) 0.16761(11) 0.0239(3) Uani 1 1 d . . .
O3 O 0.89770(9) 0.20783(10) 0.24346(10) 0.0234(3) Uani 1 1 d . . .
S1 S 0.93653(3) 0.14948(3) 0.14556(3) 0.01767(13) Uani 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
C1 0.0195(7) 0.0118(7) 0.0215(8) -0.0003(6) -0.0033(6) -0.0018(6)
C2 0.0208(8) 0.0129(7) 0.0202(8) -0.0017(6) 0.0002(6) -0.0006(6)
C3 0.0246(8) 0.0139(7) 0.0212(8) 0.0007(6) 0.0001(6) 0.0004(6)
C4 0.0289(9) 0.0190(8) 0.0200(8) -0.0009(7) -0.0041(7) 0.0008(7)
C5 0.0263(8) 0.0184(8) 0.0240(9) -0.0039(7) -0.0059(7) -0.0014(6)
C6 0.0267(8) 0.0130(7) 0.0251(9) -0.0029(7) -0.0047(7) -0.0015(6)
C7 0.0241(8) 0.0133(7) 0.0242(9) 0.0009(6) -0.0045(7) -0.0016(6)
C8 0.0256(9) 0.0194(8) 0.0301(10) 0.0042(7) -0.0023(7) -0.0018(7)
C9 0.0285(9) 0.0240(9) 0.0348(10) 0.0077(8) 0.0023(8) -0.0030(7)
C10 0.0383(11) 0.0261(10) 0.0545(13) 0.0194(10) 0.0019(10) -0.0032(8)
C11 0.0264(9) 0.0263(9) 0.0300(10) 0.0004(7) -0.0004(7) 0.0061(7)
C12 0.0197(7) 0.0118(7) 0.0213(8) 0.0003(6) -0.0051(6) -0.0003(6)
C13 0.0249(8) 0.0132(7) 0.0213(8) -0.0024(6) -0.0029(6) -0.0006(6)
C14 0.0251(8) 0.0187(8) 0.0207(8) -0.0013(6) -0.0010(6) 0.0003(6)
C15 0.0240(8) 0.0166(8) 0.0237(8) 0.0022(7) -0.0060(7) -0.0034(6)
C16 0.0297(9) 0.0116(7) 0.0256(9) -0.0016(6) -0.0052(7) -0.0027(6)
C17 0.0257(8) 0.0142(8) 0.0206(8) -0.0027(6) -0.0037(7) 0.0001(6)
C18 0.0380(10) 0.0239(9) 0.0277(10) 0.0020(8) 0.0009(8) -0.0106(8)
N1 0.0209(7) 0.0106(6) 0.0206(7) -0.0005(5) -0.0027(5) -0.0017(5)
O1 0.0308(6) 0.0123(5) 0.0282(7) 0.0037(5) 0.0034(5) 0.0009(5)
O2 0.0280(6) 0.0145(6) 0.0284(7) 0.0048(5) -0.0069(5) 0.0000(5)
O3 0.0286(6) 0.0209(6) 0.0205(6) -0.0044(5) 0.0004(5) -0.0063(5)
S1 0.0214(2) 0.0126(2) 0.0186(2) -0.00005(14) -0.00332(15) -0.00211(14)
_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
C1 C2 1.501(2) . ?
C1 N1 1.506(2) . ?
C1 C7 1.519(2) . ?
C1 C6 1.526(2) . ?
C2 N1 1.483(2) . ?
C2 C3 1.518(2) . ?
C2 H2 1.0000 . ?
C3 O1 1.4338(19) . ?
C3 C11 1.524(2) . ?
C3 C4 1.532(2) . ?
C4 C5 1.531(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.528(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.531(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.526(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.520(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.394(2) . ?
C12 C13 1.395(2) . ?
C12 S1 1.7570(16) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.398(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(3) . ?
C15 C18 1.507(2) . ?
C16 C17 1.387(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1 S1 1.6583(14) . ?
O1 H1 0.8400 . ?
O2 S1 1.4404(12) . ?
O3 S1 1.4434(12) . ?
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

C2 C1 N1 59.09(10) . . ?
C2 C1 C7 117.76(14) . . ?
N1 C1 C7 121.37(13) . . ?
C2 C1 C6 118.75(14) . . ?
N1 C1 C6 111.49(13) . . ?
C7 C1 C6 116.23(13) . . ?
N1 C2 C1 60.61(10) . . ?
N1 C2 C3 116.79(13) . . ?
C1 C2 C3 123.04(14) . . ?
N1 C2 H2 115.1 . . ?
C1 C2 H2 115.1 . . ?
C3 C2 H2 115.1 . . ?
O1 C3 C2 109.29(13) . . ?
O1 C3 C11 105.61(13) . . ?
C2 C3 C11 108.23(14) . . ?
O1 C3 C4 110.30(13) . . ?
C2 C3 C4 111.25(13) . . ?
C11 C3 C4 111.97(14) . . ?
C5 C4 C3 112.35(14) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 110.23(14) . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C1 C6 C5 111.87(13) . . ?
C1 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C1 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C1 C7 C8 110.45(13) . . ?
C1 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C1 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C7 113.60(14) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 114.00(17) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 121.12(15) . . ?
C17 C12 S1 119.77(13) . . ?
C13 C12 S1 119.11(12) . . ?
C14 C13 C12 118.84(15) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 121.33(16) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 118.59(15) . . ?
C16 C15 C18 121.49(15) . . ?
C14 C15 C18 119.90(16) . . ?
C17 C16 C15 121.23(15) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C12 118.89(16) . . ?
C16 C17 H17 120.6 . . ?
C12 C17 H17 120.6 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 N1 C1 60.30(10) . . ?
C2 N1 S1 119.54(11) . . ?
C1 N1 S1 121.43(11) . . ?
C3 O1 H1 109.5 . . ?
O2 S1 O3 117.98(7) . . ?
O2 S1 N1 106.30(7) . . ?
O3 S1 N1 112.96(7) . . ?
O2 S1 C12 109.98(7) . . ?
O3 S1 C12 107.69(7) . . ?
N1 S1 C12 100.53(7) . . ?
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

C7 C1 C2 N1 111.75(15) . . . . ?
C6 C1 C2 N1 -99.12(16) . . . . ?
N1 C1 C2 C3 104.52(16) . . . . ?
C7 C1 C2 C3 -143.73(15) . . . . ?
C6 C1 C2 C3 5.4(2) . . . . ?
N1 C2 C3 O1 -66.62(17) . . . . ?
C1 C2 C3 O1 -137.51(15) . . . . ?
N1 C2 C3 C11 178.84(13) . . . . ?
C1 C2 C3 C11 107.95(17) . . . . ?
N1 C2 C3 C4 55.42(18) . . . . ?
C1 C2 C3 C4 -15.5(2) . . . . ?
O1 C3 C4 C5 166.39(13) . . . . ?
C2 C3 C4 C5 44.94(19) . . . . ?
C11 C3 C4 C5 -76.32(18) . . . . ?
C3 C4 C5 C6 -66.18(19) . . . . ?
C2 C1 C6 C5 -23.9(2) . . . . ?
N1 C1 C6 C5 -89.50(16) . . . . ?
C7 C1 C6 C5 125.65(15) . . . . ?
C4 C5 C6 C1 53.13(19) . . . . ?
C2 C1 C7 C8 80.27(17) . . . . ?
N1 C1 C7 C8 149.23(14) . . . . ?
C6 C1 C7 C8 -69.64(18) . . . . ?
C1 C7 C8 C9 179.50(14) . . . . ?
C7 C8 C9 C10 -69.7(2) . . . . ?
C17 C12 C13 C14 0.1(2) . . . . ?
S1 C12 C13 C14 -179.25(12) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C13 C14 C15 C18 -178.57(16) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C18 C15 C16 C17 178.26(16) . . . . ?
C15 C16 C17 C12 0.5(2) . . . . ?
C13 C12 C17 C16 -0.3(2) . . . . ?
S1 C12 C17 C16 178.97(12) . . . . ?
C3 C2 N1 C1 -114.62(16) . . . . ?
C1 C2 N1 S1 -111.52(13) . . . . ?
C3 C2 N1 S1 133.85(12) . . . . ?
C7 C1 N1 C2 -105.71(16) . . . . ?
C6 C1 N1 C2 111.51(15) . . . . ?
C2 C1 N1 S1 108.45(13) . . . . ?
C7 C1 N1 S1 2.7(2) . . . . ?
C6 C1 N1 S1 -140.03(12) . . . . ?
C2 N1 S1 O2 138.71(12) . . . . ?
C1 N1 S1 O2 67.44(13) . . . . ?
C2 N1 S1 O3 7.81(14) . . . . ?
C1 N1 S1 O3 -63.46(13) . . . . ?
C2 N1 S1 C12 -106.68(12) . . . . ?
C1 N1 S1 C12 -177.95(12) . . . . ?
C17 C12 S1 O2 -124.94(13) . . . . ?
C13 C12 S1 O2 54.40(15) . . . . ?
C17 C12 S1 O3 4.85(15) . . . . ?
C13 C12 S1 O3 -175.81(12) . . . . ?
C17 C12 S1 N1 123.26(13) . . . . ?
C13 C12 S1 N1 -57.40(14) . . . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.066