# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cm_obc_1a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H29 N O2 S2'
_chemical_formula_sum            'C22 H29 N O2 S2'
_chemical_formula_weight         403.58

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                   15.737(4)
_cell_length_b                   14.565(3)
_cell_length_c                   20.694(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.581(3)
_cell_angle_gamma                90.00
_cell_volume                     4410.6(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    18694
_cell_measurement_theta_min      1.3981
_cell_measurement_theta_max      32.7742

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1728
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7626
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31620
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         27.44
_reflns_number_total             10025
_reflns_number_gt                8956
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0152P)²+4.3827P] where P=(Fo²+2Fc²)/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         10025
_refine_ls_number_parameters     499
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0830
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1357
_refine_ls_goodness_of_fit_ref   1.271
_refine_ls_restrained_S_all      1.271
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.01722(5) 0.06938(5) 0.22458(4) 0.02796(17) Uani 1 1 d . . .
S2 S 0.07011(5) 0.01337(5) 0.10795(4) 0.02760(17) Uani 1 1 d . . .
S3 S 0.52106(5) -0.78653(5) 0.04689(4) 0.03022(18) Uani 1 1 d . . .
S4 S 0.45216(5) -0.71219(5) 0.15064(4) 0.03167(18) Uani 1 1 d . . .
O1 O 0.05671(15) 0.09240(15) 0.29777(11) 0.0355(5) Uani 1 1 d . . .
O2 O -0.05070(14) -0.00248(14) 0.20347(12) 0.0357(5) Uani 1 1 d . . .
O3 O 0.57548(14) -0.70408(15) 0.05635(12) 0.0378(5) Uani 1 1 d . . .
O4 O 0.48990(15) -0.83092(16) -0.02062(11) 0.0373(5) Uani 1 1 d . . .
N1 N 0.27644(16) 0.04678(17) 0.24418(13) 0.0279(5) Uani 1 1 d . . .
N2 N 0.25653(16) -0.78176(17) 0.01737(13) 0.0288(6) Uani 1 1 d . . .
C1 C -0.1638(3) 0.4194(2) 0.0790(2) 0.0522(10) Uani 1 1 d . . .
H1A H -0.1527 0.4262 0.0356 0.078 Uiso 1 1 calc R . .
H1C H -0.1375 0.4719 0.1094 0.078 Uiso 1 1 calc R . .
H1B H -0.2298 0.4169 0.0686 0.078 Uiso 1 1 calc R . .
C2 C -0.1198(2) 0.3318(2) 0.11498(17) 0.0331(7) Uani 1 1 d . . .
C3 C -0.1663(2) 0.2489(2) 0.10144(18) 0.0386(8) Uani 1 1 d . . .
H3 H -0.2279 0.2474 0.0698 0.046 Uiso 1 1 calc R . .
C4 C -0.1249(2) 0.1678(2) 0.13310(17) 0.0337(7) Uani 1 1 d . . .
H4 H -0.1576 0.1115 0.1229 0.040 Uiso 1 1 calc R . .
C5 C -0.0355(2) 0.1704(2) 0.17967(16) 0.0270(6) Uani 1 1 d . . .
C6 C 0.0127(2) 0.2528(2) 0.19502(17) 0.0332(7) Uani 1 1 d . . .
H6 H 0.0740 0.2543 0.2273 0.040 Uiso 1 1 calc R . .
C7 C -0.0301(2) 0.3326(2) 0.16249(17) 0.0350(7) Uani 1 1 d . . .
H7 H 0.0025 0.3889 0.1728 0.042 Uiso 1 1 calc R . .
C8 C 0.10630(19) 0.0436(2) 0.19598(16) 0.0266(6) Uani 1 1 d . . .
C9 C 0.1922(2) 0.06150(19) 0.24312(16) 0.0272(6) Uani 1 1 d . . .
H9 H 0.1917 0.0908 0.2840 0.033 Uiso 1 1 calc R . .
C10 C 0.3548(2) 0.0775(2) 0.30686(17) 0.0366(8) Uani 1 1 d . . .
H10 H 0.4116 0.0516 0.3030 0.044 Uiso 1 1 calc R . .
C11 C 0.3491(2) 0.0405(3) 0.37383(19) 0.0560(11) Uani 1 1 d . . .
H11B H 0.2970 0.0685 0.3815 0.084 Uiso 1 1 calc R . .
H11C H 0.4055 0.0554 0.4129 0.084 Uiso 1 1 calc R . .
H11A H 0.3411 -0.0263 0.3703 0.084 Uiso 1 1 calc R . .
C12 C 0.3640(3) 0.1814(3) 0.3078(2) 0.0525(10) Uani 1 1 d . . .
H12A H 0.3717 0.2018 0.2652 0.079 Uiso 1 1 calc R . .
H12C H 0.4173 0.1999 0.3483 0.079 Uiso 1 1 calc R . .
H12B H 0.3088 0.2093 0.3107 0.079 Uiso 1 1 calc R . .
C13 C 0.2962(2) -0.0103(2) 0.19212(18) 0.0372(8) Uani 1 1 d . . .
H13 H 0.2378 -0.0171 0.1511 0.045 Uiso 1 1 calc R . .
C14 C 0.3254(3) -0.1061(3) 0.2217(2) 0.0608(12) Uani 1 1 d . . .
H14C H 0.3813 -0.1017 0.2632 0.091 Uiso 1 1 calc R . .
H14B H 0.3370 -0.1442 0.1868 0.091 Uiso 1 1 calc R . .
H14A H 0.2768 -0.1338 0.2340 0.091 Uiso 1 1 calc R . .
C15 C 0.3655(2) 0.0351(3) 0.16638(19) 0.0526(10) Uani 1 1 d . . .
H15A H 0.3436 0.0963 0.1481 0.079 Uiso 1 1 calc R . .
H15B H 0.3729 -0.0025 0.1295 0.079 Uiso 1 1 calc R . .
H15C H 0.4245 0.0406 0.2050 0.079 Uiso 1 1 calc R . .
C16 C 0.07426(19) -0.1094(2) 0.10716(16) 0.0272(6) Uani 1 1 d . . .
C17 C 0.0713(2) -0.1640(2) 0.16105(17) 0.0320(7) Uani 1 1 d . . .
H17 H 0.0672 -0.1368 0.2015 0.038 Uiso 1 1 calc R . .
C18 C 0.0743(2) -0.2591(2) 0.15544(18) 0.0350(7) Uani 1 1 d . . .
H18 H 0.0725 -0.2963 0.1926 0.042 Uiso 1 1 calc R . .
C19 C 0.0800(2) -0.3010(2) 0.09718(18) 0.0347(7) Uani 1 1 d . . .
C20 C 0.0823(2) -0.2450(2) 0.04398(18) 0.0386(8) Uani 1 1 d . . .
H20 H 0.0858 -0.2723 0.0034 0.046 Uiso 1 1 calc R . .
C21 C 0.0797(2) -0.1500(2) 0.04801(17) 0.0339(7) Uani 1 1 d . . .
H21 H 0.0816 -0.1130 0.0107 0.041 Uiso 1 1 calc R . .
C22 C 0.0839(3) -0.4048(2) 0.0920(2) 0.0510(10) Uani 1 1 d . . .
H22A H 0.0488 -0.4240 0.0442 0.076 Uiso 1 1 calc R . .
H22C H 0.0578 -0.4330 0.1235 0.076 Uiso 1 1 calc R . .
H22B H 0.1476 -0.4243 0.1050 0.076 Uiso 1 1 calc R . .
C23 C 0.7642(2) -1.0650(2) 0.25003(19) 0.0436(9) Uani 1 1 d . . .
H23B H 0.8249 -1.0622 0.2472 0.065 Uiso 1 1 calc R . .
H23C H 0.7389 -1.1269 0.2376 0.065 Uiso 1 1 calc R . .
H23A H 0.7691 -1.0507 0.2975 0.065 Uiso 1 1 calc R . .
C24 C 0.7019(2) -0.9960(2) 0.20027(18) 0.0353(7) Uani 1 1 d . . .
C25 C 0.7217(2) -0.9027(2) 0.20849(18) 0.0378(8) Uani 1 1 d . . .
H25 H 0.7745 -0.8827 0.2460 0.045 Uiso 1 1 calc R . .
C26 C 0.6661(2) -0.8382(2) 0.16309(17) 0.0345(7) Uani 1 1 d . . .
H26 H 0.6806 -0.7747 0.1695 0.041 Uiso 1 1 calc R . .
C27 C 0.5893(2) -0.8673(2) 0.10826(16) 0.0299(7) Uani 1 1 d . . .
C28 C 0.5670(2) -0.9601(2) 0.09944(17) 0.0348(7) Uani 1 1 d . . .
H28 H 0.5135 -0.9798 0.0624 0.042 Uiso 1 1 calc R . .
C29 C 0.6238(2) -1.0239(2) 0.14538(17) 0.0356(7) Uani 1 1 d . . .
H29 H 0.6090 -1.0873 0.1392 0.043 Uiso 1 1 calc R . .
C30 C 0.4257(2) -0.7633(2) 0.06881(16) 0.0293(7) Uani 1 1 d . . .
C31 C 0.3431(2) -0.7933(2) 0.02250(16) 0.0275(6) Uani 1 1 d . . .
H31 H 0.3486 -0.8302 -0.0136 0.033 Uiso 1 1 calc R . .
C32 C 0.2272(2) -0.7157(2) 0.05935(17) 0.0331(7) Uani 1 1 d . . .
H32 H 0.2837 -0.6897 0.0953 0.040 Uiso 1 1 calc R . .
C33 C 0.1724(2) -0.7617(2) 0.09749(19) 0.0418(8) Uani 1 1 d . . .
H33A H 0.1581 -0.7166 0.1271 0.063 Uiso 1 1 calc R . .
H33C H 0.2083 -0.8119 0.1263 0.063 Uiso 1 1 calc R . .
H33B H 0.1155 -0.7863 0.0636 0.063 Uiso 1 1 calc R . .
C34 C 0.1748(3) -0.6358(2) 0.0139(2) 0.0564(11) Uani 1 1 d . . .
H34C H 0.1195 -0.6593 -0.0226 0.085 Uiso 1 1 calc R . .
H34B H 0.2136 -0.6056 -0.0075 0.085 Uiso 1 1 calc R . .
H34A H 0.1578 -0.5915 0.0426 0.085 Uiso 1 1 calc R . .
C35 C 0.1837(2) -0.8307(2) -0.04005(16) 0.0320(7) Uani 1 1 d . . .
H35 H 0.1238 -0.8133 -0.0371 0.038 Uiso 1 1 calc R . .
C36 C 0.1935(2) -0.9342(2) -0.03012(19) 0.0425(8) Uani 1 1 d . . .
H36C H 0.2503 -0.9543 -0.0349 0.064 Uiso 1 1 calc R . .
H36B H 0.1415 -0.9647 -0.0654 0.064 Uiso 1 1 calc R . .
H36A H 0.1950 -0.9503 0.0163 0.064 Uiso 1 1 calc R . .
C37 C 0.1808(2) -0.8010(3) -0.11125(18) 0.0458(9) Uani 1 1 d . . .
H37A H 0.1704 -0.7346 -0.1165 0.069 Uiso 1 1 calc R . .
H37B H 0.1310 -0.8331 -0.1473 0.069 Uiso 1 1 calc R . .
H37C H 0.2390 -0.8161 -0.1158 0.069 Uiso 1 1 calc R . .
C38 C 0.42912(19) -0.5928(2) 0.13282(16) 0.0284(7) Uani 1 1 d . . .
C39 C 0.4165(2) -0.5403(2) 0.18449(17) 0.0356(7) Uani 1 1 d . . .
H39 H 0.4213 -0.5681 0.2272 0.043 Uiso 1 1 calc R . .
C40 C 0.3969(2) -0.4475(2) 0.1740(2) 0.0415(8) Uani 1 1 d . . .
H40 H 0.3887 -0.4125 0.2100 0.050 Uiso 1 1 calc R . .
C41 C 0.3889(2) -0.4046(2) 0.11210(19) 0.0385(8) Uani 1 1 d . . .
C42 C 0.4025(2) -0.4580(2) 0.06093(17) 0.0347(7) Uani 1 1 d . . .
H42 H 0.3979 -0.4303 0.0182 0.042 Uiso 1 1 calc R . .
C43 C 0.4226(2) -0.5511(2) 0.07124(17) 0.0337(7) Uani 1 1 d . . .
H43 H 0.4320 -0.5862 0.0357 0.040 Uiso 1 1 calc R . .
C44 C 0.3655(3) -0.3034(2) 0.1003(2) 0.0539(10) Uani 1 1 d . . .
H44A H 0.3006 -0.2944 0.0920 0.081 Uiso 1 1 calc R . .
H44B H 0.3782 -0.2819 0.0599 0.081 Uiso 1 1 calc R . .
H44C H 0.4026 -0.2684 0.1415 0.081 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.444(2) . ?
S1 O1 1.449(2) . ?
S1 C8 1.751(3) . ?
S1 C5 1.775(3) . ?
S2 C8 1.753(3) . ?
S2 C16 1.789(3) . ?
S3 O3 1.446(2) . ?
S3 O4 1.451(2) . ?
S3 C30 1.753(3) . ?
S3 C27 1.774(3) . ?
S4 C30 1.754(3) . ?
S4 C38 1.787(3) . ?
N1 C9 1.336(4) . ?
N1 C13 1.482(4) . ?
N1 C10 1.492(4) . ?
N2 C31 1.338(4) . ?
N2 C32 1.480(4) . ?
N2 C35 1.494(4) . ?
C1 C2 1.510(4) . ?
C1 H1A 0.9800 . ?
C1 H1C 0.9800 . ?
C1 H1B 0.9800 . ?
C2 C3 1.386(5) . ?
C2 C7 1.393(4) . ?
C3 C4 1.391(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(4) . ?
C6 C7 1.387(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.370(4) . ?
C9 H9 0.9500 . ?
C10 C12 1.519(5) . ?
C10 C11 1.520(5) . ?
C10 H10 1.0000 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 H11A 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12C 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C14 1.524(5) . ?
C13 C15 1.529(5) . ?
C13 H13 1.0000 . ?
C14 H14C 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14A 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.385(4) . ?
C16 C21 1.390(4) . ?
C17 C18 1.393(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(5) . ?
C19 C22 1.519(4) . ?
C20 C21 1.388(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22C 0.9800 . ?
C22 H22B 0.9800 . ?
C23 C24 1.513(4) . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 H23A 0.9800 . ?
C24 C25 1.392(5) . ?
C24 C29 1.392(5) . ?
C25 C26 1.388(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.392(4) . ?
C28 C29 1.393(4) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C31 1.372(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.523(4) . ?
C32 C34 1.532(5) . ?
C32 H32 1.0000 . ?
C33 H33A 0.9800 . ?
C33 H33C 0.9800 . ?
C33 H33B 0.9800 . ?
C34 H34C 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34A 0.9800 . ?
C35 C37 1.520(4) . ?
C35 C36 1.521(4) . ?
C35 H35 1.0000 . ?
C36 H36C 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36A 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C43 1.381(4) . ?
C38 C39 1.387(4) . ?
C39 C40 1.386(5) . ?
C39 H39 0.9500 . ?
C40 C41 1.389(5) . ?
C40 H40 0.9500 . ?
C41 C42 1.392(5) . ?
C41 C44 1.517(5) . ?
C42 C43 1.392(4) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 117.97(14) . . ?
O2 S1 C8 109.73(14) . . ?
O1 S1 C8 108.30(14) . . ?
O2 S1 C5 106.91(14) . . ?
O1 S1 C5 107.08(14) . . ?
C8 S1 C5 106.22(14) . . ?
C8 S2 C16 105.14(14) . . ?
O3 S3 O4 118.29(14) . . ?
O3 S3 C30 109.00(14) . . ?
O4 S3 C30 108.46(14) . . ?
O3 S3 C27 106.35(14) . . ?
O4 S3 C27 107.16(14) . . ?
C30 S3 C27 107.03(14) . . ?
C30 S4 C38 104.82(14) . . ?
C9 N1 C13 123.5(3) . . ?
C9 N1 C10 117.7(3) . . ?
C13 N1 C10 118.2(2) . . ?
C31 N2 C32 124.3(3) . . ?
C31 N2 C35 117.6(3) . . ?
C32 N2 C35 117.6(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1C C1 H1B 109.5 . . ?
C3 C2 C7 118.1(3) . . ?
C3 C2 C1 121.6(3) . . ?
C7 C2 C1 120.2(3) . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 S1 120.2(2) . . ?
C6 C5 S1 118.9(2) . . ?
C7 C6 C5 119.0(3) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C2 121.4(3) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
C9 C8 S1 114.9(2) . . ?
C9 C8 S2 130.3(2) . . ?
S1 C8 S2 114.24(16) . . ?
N1 C9 C8 134.0(3) . . ?
N1 C9 H9 113.0 . . ?
C8 C9 H9 113.0 . . ?
N1 C10 C12 110.7(3) . . ?
N1 C10 C11 112.3(3) . . ?
C12 C10 C11 112.2(3) . . ?
N1 C10 H10 107.1 . . ?
C12 C10 H10 107.1 . . ?
C11 C10 H10 107.1 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
H11B C11 H11A 109.5 . . ?
H11C C11 H11A 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
N1 C13 C14 109.6(3) . . ?
N1 C13 C15 112.2(3) . . ?
C14 C13 C15 112.8(3) . . ?
N1 C13 H13 107.3 . . ?
C14 C13 H13 107.3 . . ?
C15 C13 H13 107.3 . . ?
C13 C14 H14C 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14C C14 H14B 109.5 . . ?
C13 C14 H14A 109.5 . . ?
H14C C14 H14A 109.5 . . ?
H14B C14 H14A 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 119.8(3) . . ?
C17 C16 S2 123.7(2) . . ?
C21 C16 S2 116.6(2) . . ?
C16 C17 C18 119.5(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 121.8(3) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C20 C19 C18 117.6(3) . . ?
C20 C19 C22 121.2(3) . . ?
C18 C19 C22 121.2(3) . . ?
C19 C20 C21 122.1(3) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C20 C21 C16 119.3(3) . . ?
C20 C21 H21 120.3 . . ?
C16 C21 H21 120.3 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22C C22 H22B 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
H23B C23 H23A 109.5 . . ?
H23C C23 H23A 109.5 . . ?
C25 C24 C29 118.4(3) . . ?
C25 C24 C23 120.4(3) . . ?
C29 C24 C23 121.2(3) . . ?
C26 C25 C24 121.4(3) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C27 C26 C25 119.4(3) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C27 C28 120.4(3) . . ?
C26 C27 S3 120.0(2) . . ?
C28 C27 S3 119.6(2) . . ?
C27 C28 C29 119.4(3) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C24 C29 C28 121.0(3) . . ?
C24 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C31 C30 S3 116.0(2) . . ?
C31 C30 S4 129.6(2) . . ?
S3 C30 S4 114.18(17) . . ?
N2 C31 C30 133.7(3) . . ?
N2 C31 H31 113.2 . . ?
C30 C31 H31 113.2 . . ?
N2 C32 C33 112.1(3) . . ?
N2 C32 C34 110.3(3) . . ?
C33 C32 C34 111.9(3) . . ?
N2 C32 H32 107.4 . . ?
C33 C32 H32 107.4 . . ?
C34 C32 H32 107.4 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33C C33 H33B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34C C34 H34B 109.5 . . ?
C32 C34 H34A 109.5 . . ?
H34C C34 H34A 109.5 . . ?
H34B C34 H34A 109.5 . . ?
N2 C35 C37 112.1(3) . . ?
N2 C35 C36 110.8(3) . . ?
C37 C35 C36 112.2(3) . . ?
N2 C35 H35 107.1 . . ?
C37 C35 H35 107.1 . . ?
C36 C35 H35 107.1 . . ?
C35 C36 H36C 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36C C36 H36B 109.5 . . ?
C35 C36 H36A 109.5 . . ?
H36C C36 H36A 109.5 . . ?
H36B C36 H36A 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C43 C38 C39 119.1(3) . . ?
C43 C38 S4 124.0(2) . . ?
C39 C38 S4 116.9(2) . . ?
C40 C39 C38 120.2(3) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C39 C40 C41 121.6(3) . . ?
C39 C40 H40 119.2 . . ?
C41 C40 H40 119.2 . . ?
C40 C41 C42 117.6(3) . . ?
C40 C41 C44 121.3(3) . . ?
C42 C41 C44 121.1(3) . . ?
C43 C42 C41 121.2(3) . . ?
C43 C42 H42 119.4 . . ?
C41 C42 H42 119.4 . . ?
C38 C43 C42 120.4(3) . . ?
C38 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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
C7 C2 C3 C4 -1.0(5) . . . . ?
C1 C2 C3 C4 178.1(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C3 C4 C5 S1 176.5(3) . . . . ?
O2 S1 C5 C4 -1.9(3) . . . . ?
O1 S1 C5 C4 -129.2(3) . . . . ?
C8 S1 C5 C4 115.2(3) . . . . ?
O2 S1 C5 C6 174.5(2) . . . . ?
O1 S1 C5 C6 47.2(3) . . . . ?
C8 S1 C5 C6 -68.3(3) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
S1 C5 C6 C7 -176.8(2) . . . . ?
C5 C6 C7 C2 -0.1(5) . . . . ?
C3 C2 C7 C6 0.8(5) . . . . ?
C1 C2 C7 C6 -178.4(3) . . . . ?
O2 S1 C8 C9 -138.4(2) . . . . ?
O1 S1 C8 C9 -8.3(3) . . . . ?
C5 S1 C8 C9 106.4(2) . . . . ?
O2 S1 C8 S2 49.6(2) . . . . ?
O1 S1 C8 S2 179.65(15) . . . . ?
C5 S1 C8 S2 -65.6(2) . . . . ?
C16 S2 C8 C9 89.9(3) . . . . ?
C16 S2 C8 S1 -99.60(18) . . . . ?
C13 N1 C9 C8 -9.8(5) . . . . ?
C10 N1 C9 C8 179.8(3) . . . . ?
S1 C8 C9 N1 174.8(3) . . . . ?
S2 C8 C9 N1 -14.7(5) . . . . ?
C9 N1 C10 C12 -73.5(4) . . . . ?
C13 N1 C10 C12 115.7(3) . . . . ?
C9 N1 C10 C11 52.8(4) . . . . ?
C13 N1 C10 C11 -118.0(3) . . . . ?
C9 N1 C13 C14 -98.8(4) . . . . ?
C10 N1 C13 C14 71.5(4) . . . . ?
C9 N1 C13 C15 135.1(3) . . . . ?
C10 N1 C13 C15 -54.6(4) . . . . ?
C8 S2 C16 C17 22.3(3) . . . . ?
C8 S2 C16 C21 -158.5(2) . . . . ?
C21 C16 C17 C18 0.4(5) . . . . ?
S2 C16 C17 C18 179.6(2) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C20 -0.2(5) . . . . ?
C17 C18 C19 C22 179.6(3) . . . . ?
C18 C19 C20 C21 0.4(5) . . . . ?
C22 C19 C20 C21 -179.4(3) . . . . ?
C19 C20 C21 C16 -0.2(5) . . . . ?
C17 C16 C21 C20 -0.2(5) . . . . ?
S2 C16 C21 C20 -179.5(3) . . . . ?
C29 C24 C25 C26 -0.6(5) . . . . ?
C23 C24 C25 C26 179.3(3) . . . . ?
C24 C25 C26 C27 -0.2(5) . . . . ?
C25 C26 C27 C28 1.2(5) . . . . ?
C25 C26 C27 S3 -176.4(2) . . . . ?
O3 S3 C27 C26 15.6(3) . . . . ?
O4 S3 C27 C26 143.0(3) . . . . ?
C30 S3 C27 C26 -100.8(3) . . . . ?
O3 S3 C27 C28 -162.0(2) . . . . ?
O4 S3 C27 C28 -34.6(3) . . . . ?
C30 S3 C27 C28 81.6(3) . . . . ?
C26 C27 C28 C29 -1.4(5) . . . . ?
S3 C27 C28 C29 176.2(2) . . . . ?
C25 C24 C29 C28 0.4(5) . . . . ?
C23 C24 C29 C28 -179.6(3) . . . . ?
C27 C28 C29 C24 0.6(5) . . . . ?
O3 S3 C30 C31 132.9(2) . . . . ?
O4 S3 C30 C31 2.8(3) . . . . ?
C27 S3 C30 C31 -112.5(2) . . . . ?
O3 S3 C30 S4 -51.6(2) . . . . ?
O4 S3 C30 S4 178.31(16) . . . . ?
C27 S3 C30 S4 63.0(2) . . . . ?
C38 S4 C30 C31 -85.0(3) . . . . ?
C38 S4 C30 S3 100.30(18) . . . . ?
C32 N2 C31 C30 10.6(5) . . . . ?
C35 N2 C31 C30 -176.9(3) . . . . ?
S3 C30 C31 N2 -172.7(3) . . . . ?
S4 C30 C31 N2 12.7(5) . . . . ?
C31 N2 C32 C33 -125.7(3) . . . . ?
C35 N2 C32 C33 61.8(4) . . . . ?
C31 N2 C32 C34 108.9(3) . . . . ?
C35 N2 C32 C34 -63.6(3) . . . . ?
C31 N2 C35 C37 -61.3(4) . . . . ?
C32 N2 C35 C37 111.8(3) . . . . ?
C31 N2 C35 C36 65.0(4) . . . . ?
C32 N2 C35 C36 -122.0(3) . . . . ?
C30 S4 C38 C43 -19.1(3) . . . . ?
C30 S4 C38 C39 160.4(2) . . . . ?
C43 C38 C39 C40 0.5(5) . . . . ?
S4 C38 C39 C40 -178.9(2) . . . . ?
C38 C39 C40 C41 0.3(5) . . . . ?
C39 C40 C41 C42 -0.8(5) . . . . ?
C39 C40 C41 C44 178.8(3) . . . . ?
C40 C41 C42 C43 0.5(5) . . . . ?
C44 C41 C42 C43 -179.1(3) . . . . ?
C39 C38 C43 C42 -0.9(5) . . . . ?
S4 C38 C43 C42 178.6(2) . . . . ?
C41 C42 C43 C38 0.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 997482'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cm_obc_1b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 N O2 S'
_chemical_formula_sum            'C13 H19 N O2 S'
_chemical_formula_weight         253.35

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                   22.425(5)
_cell_length_b                   8.478(3)
_cell_length_c                   14.695(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.438(4)
_cell_angle_gamma                90.00
_cell_volume                     2650.4(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8077
_cell_measurement_theta_min      1.47
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6895
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18441
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6022
_reflns_number_gt                5196
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 Ver 1.1'
_computing_molecular_graphics    'Olex2 Ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0382P)²+3.8031P] where P=(Fo²+2Fc²)/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         6022
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0809
_refine_ls_wR_factor_ref         0.1662
_refine_ls_wR_factor_gt          0.1577
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.61777(4) -0.13621(9) 0.61181(5) 0.02447(19) Uani 1 1 d . . .
S1A S 0.10348(4) 0.65623(9) 0.48932(5) 0.02379(19) Uani 1 1 d . . .
O1 O 0.57406(11) -0.1032(3) 0.51827(15) 0.0330(5) Uani 1 1 d . . .
O1A O 0.05733(11) 0.6355(3) 0.53865(15) 0.0279(5) Uani 1 1 d . . .
O2 O 0.66102(11) -0.2657(3) 0.62253(17) 0.0356(6) Uani 1 1 d . . .
O2A O 0.14328(11) 0.7943(3) 0.51121(16) 0.0308(5) Uani 1 1 d . . .
N7 N 0.47585(12) -0.1603(3) 0.71564(19) 0.0280(6) Uani 1 1 d . . .
N7A N -0.02836(12) 0.5921(3) 0.24050(18) 0.0260(6) Uani 1 1 d . . .
C1 C 0.66426(14) 0.0349(4) 0.6472(2) 0.0239(6) Uani 1 1 d . . .
C1A C 0.15396(14) 0.4908(3) 0.5174(2) 0.0224(6) Uani 1 1 d . . .
C2 C 0.64165(15) 0.1802(4) 0.6067(2) 0.0242(6) Uani 1 1 d . . .
H2 H 0.6011 0.1879 0.5604 0.029 Uiso 1 1 calc R . .
C2A C 0.13028(14) 0.3466(4) 0.5358(2) 0.0227(6) Uani 1 1 d . . .
H2A H 0.0886 0.3393 0.5383 0.027 Uiso 1 1 calc R . .
C3 C 0.67881(14) 0.3143(4) 0.6343(2) 0.0248(6) Uani 1 1 d . . .
H3 H 0.6635 0.4131 0.6060 0.030 Uiso 1 1 calc R . .
C3A C 0.16830(15) 0.2137(4) 0.5504(2) 0.0255(7) Uani 1 1 d . . .
H3A H 0.1523 0.1152 0.5632 0.031 Uiso 1 1 calc R . .
C4 C 0.73792(14) 0.3057(4) 0.7027(2) 0.0247(6) Uani 1 1 d . . .
C4A C 0.22951(16) 0.2222(4) 0.5466(2) 0.0298(7) Uani 1 1 d . . .
C5 C 0.75921(14) 0.1599(4) 0.7433(2) 0.0273(7) Uani 1 1 d . . .
H5 H 0.7995 0.1524 0.7901 0.033 Uiso 1 1 calc R . .
C5A C 0.25240(15) 0.3686(4) 0.5291(2) 0.0303(7) Uani 1 1 d . . .
H5A H 0.2942 0.3766 0.5271 0.036 Uiso 1 1 calc R . .
C6 C 0.72280(14) 0.0254(4) 0.7167(2) 0.0255(7) Uani 1 1 d . . .
H6 H 0.7378 -0.0730 0.7460 0.031 Uiso 1 1 calc R . .
C6A C 0.21503(15) 0.5019(4) 0.5145(2) 0.0271(7) Uani 1 1 d . . .
H6A H 0.2311 0.6007 0.5026 0.032 Uiso 1 1 calc R . .
C7 C 0.77880(16) 0.4501(4) 0.7309(2) 0.0335(8) Uani 1 1 d . . .
H7A H 0.8051 0.4602 0.6892 0.050 Uiso 1 1 calc R . .
H7B H 0.8057 0.4402 0.7978 0.050 Uiso 1 1 calc R . .
H7C H 0.7522 0.5439 0.7242 0.050 Uiso 1 1 calc R . .
C7A C 0.26956(18) 0.0771(4) 0.5604(3) 0.0406(9) Uani 1 1 d . . .
H7AA H 0.2916 0.0619 0.6289 0.061 Uiso 1 1 calc R . .
H7AB H 0.3003 0.0893 0.5261 0.061 Uiso 1 1 calc R . .
H7AC H 0.2429 -0.0147 0.5352 0.061 Uiso 1 1 calc R . .
C8 C 0.57760(16) -0.1619(4) 0.6924(2) 0.0282(7) Uani 1 1 d . . .
H8 H 0.5992 -0.1940 0.7563 0.034 Uiso 1 1 calc R . .
C8A C 0.06710(15) 0.6492(3) 0.3685(2) 0.0238(6) Uani 1 1 d . . .
H8A H 0.0891 0.6813 0.3259 0.029 Uiso 1 1 calc R . .
C9 C 0.51509(15) -0.1362(4) 0.6643(2) 0.0272(7) Uani 1 1 d . . .
H9 H 0.4967 -0.0967 0.6011 0.033 Uiso 1 1 calc R . .
C9A C 0.00671(14) 0.5976(4) 0.3327(2) 0.0245(6) Uani 1 1 d . . .
H9A H -0.0125 0.5619 0.3780 0.029 Uiso 1 1 calc R . .
C10 C 0.49689(16) -0.2165(4) 0.8148(2) 0.0305(7) Uani 1 1 d . . .
H10C H 0.5361 -0.2781 0.8261 0.037 Uiso 1 1 calc R . .
H10D H 0.4646 -0.2876 0.8250 0.037 Uiso 1 1 calc R . .
C10A C -0.00332(15) 0.6444(4) 0.1647(2) 0.0264(7) Uani 1 1 d . . .
H10A H 0.0233 0.7388 0.1871 0.032 Uiso 1 1 calc R . .
H10B H -0.0387 0.6751 0.1076 0.032 Uiso 1 1 calc R . .
C11 C 0.5086(2) -0.0832(5) 0.8857(3) 0.0501(11) Uani 1 1 d . . .
H11D H 0.5407 -0.0127 0.8760 0.075 Uiso 1 1 calc R . .
H11E H 0.5232 -0.1257 0.9510 0.075 Uiso 1 1 calc R . .
H11F H 0.4695 -0.0242 0.8762 0.075 Uiso 1 1 calc R . .
C11A C 0.03539(16) 0.5172(4) 0.1364(2) 0.0303(7) Uani 1 1 d . . .
H11A H 0.0530 0.5594 0.0883 0.045 Uiso 1 1 calc R . .
H11B H 0.0085 0.4266 0.1096 0.045 Uiso 1 1 calc R . .
H11C H 0.0697 0.4838 0.1931 0.045 Uiso 1 1 calc R . .
C12 C 0.40874(15) -0.1233(4) 0.6735(2) 0.0303(7) Uani 1 1 d . . .
H12C H 0.4030 -0.0535 0.6173 0.036 Uiso 1 1 calc R . .
H12D H 0.3945 -0.0648 0.7212 0.036 Uiso 1 1 calc R . .
C12A C -0.09492(15) 0.5499(4) 0.2126(2) 0.0272(7) Uani 1 1 d . . .
H12A H -0.1019 0.4782 0.2614 0.033 Uiso 1 1 calc R . .
H12B H -0.1066 0.4926 0.1507 0.033 Uiso 1 1 calc R . .
C13 C 0.36813(17) -0.2684(4) 0.6422(2) 0.0349(8) Uani 1 1 d . . .
H13D H 0.3775 -0.3180 0.5880 0.052 Uiso 1 1 calc R . .
H13E H 0.3237 -0.2380 0.6226 0.052 Uiso 1 1 calc R . .
H13F H 0.3769 -0.3432 0.6957 0.052 Uiso 1 1 calc R . .
C13A C -0.13682(15) 0.6930(4) 0.2025(2) 0.0287(7) Uani 1 1 d . . .
H13A H -0.1271 0.7692 0.1590 0.043 Uiso 1 1 calc R . .
H13B H -0.1295 0.7417 0.2656 0.043 Uiso 1 1 calc R . .
H13C H -0.1809 0.6607 0.1764 0.043 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.440(2) . ?
S1 O1 1.441(2) . ?
S1 C8 1.714(3) . ?
S1 C1 1.766(3) . ?
S1A O2A 1.445(2) . ?
S1A O1A 1.450(2) . ?
S1A C8A 1.705(3) . ?
S1A C1A 1.767(3) . ?
N7 C9 1.344(4) . ?
N7 C10 1.462(4) . ?
N7 C12 1.469(4) . ?
N7A C9A 1.335(4) . ?
N7A C12A 1.462(4) . ?
N7A C10A 1.465(4) . ?
C1 C6 1.388(4) . ?
C1 C2 1.392(4) . ?
C1A C6A 1.387(4) . ?
C1A C2A 1.393(4) . ?
C2 C3 1.392(4) . ?
C2 H2 0.9500 . ?
C2A C3A 1.388(4) . ?
C2A H2A 0.9500 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C3A C4A 1.393(4) . ?
C3A H3A 0.9500 . ?
C4 C5 1.389(4) . ?
C4 C7 1.507(4) . ?
C4A C5A 1.397(5) . ?
C4A C7A 1.499(5) . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C5A C6A 1.383(4) . ?
C5A H5A 0.9500 . ?
C6 H6 0.9500 . ?
C6A H6A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?
C8 C9 1.348(4) . ?
C8 H8 0.9500 . ?
C8A C9A 1.360(4) . ?
C8A H8A 0.9500 . ?
C9 H9 0.9500 . ?
C9A H9A 0.9500 . ?
C10 C11 1.503(5) . ?
C10 H10C 0.9900 . ?
C10 H10D 0.9900 . ?
C10A C11A 1.523(4) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11 H11D 0.9800 . ?
C11 H11E 0.9800 . ?
C11 H11F 0.9800 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12 C13 1.513(5) . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C12A C13A 1.512(4) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13 H13D 0.9800 . ?
C13 H13E 0.9800 . ?
C13 H13F 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.94(15) . . ?
O2 S1 C8 108.09(15) . . ?
O1 S1 C8 109.65(16) . . ?
O2 S1 C1 106.25(15) . . ?
O1 S1 C1 106.33(14) . . ?
C8 S1 C1 106.94(15) . . ?
O2A S1A O1A 118.36(13) . . ?
O2A S1A C8A 108.58(14) . . ?
O1A S1A C8A 109.55(15) . . ?
O2A S1A C1A 106.61(14) . . ?
O1A S1A C1A 107.03(14) . . ?
C8A S1A C1A 106.00(14) . . ?
C9 N7 C10 123.2(3) . . ?
C9 N7 C12 119.8(3) . . ?
C10 N7 C12 117.0(3) . . ?
C9A N7A C12A 121.0(3) . . ?
C9A N7A C10A 121.1(3) . . ?
C12A N7A C10A 117.6(2) . . ?
C6 C1 C2 119.9(3) . . ?
C6 C1 S1 120.1(2) . . ?
C2 C1 S1 120.0(2) . . ?
C6A C1A C2A 120.4(3) . . ?
C6A C1A S1A 120.3(2) . . ?
C2A C1A S1A 119.1(2) . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C3A C2A C1A 119.3(3) . . ?
C3A C2A H2A 120.4 . . ?
C1A C2A H2A 120.4 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C2A C3A C4A 121.1(3) . . ?
C2A C3A H3A 119.5 . . ?
C4A C3A H3A 119.5 . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 C7 121.0(3) . . ?
C5 C4 C7 120.6(3) . . ?
C3A C4A C5A 118.5(3) . . ?
C3A C4A C7A 120.5(3) . . ?
C5A C4A C7A 121.0(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C6A C5A C4A 120.9(3) . . ?
C6A C5A H5A 119.5 . . ?
C4A C5A H5A 119.5 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C5A C6A C1A 119.7(3) . . ?
C5A C6A H6A 120.1 . . ?
C1A C6A H6A 120.1 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4A C7A H7AA 109.5 . . ?
C4A C7A H7AB 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
C4A C7A H7AC 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C9 C8 S1 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
S1 C8 H8 120.3 . . ?
C9A C8A S1A 120.2(2) . . ?
C9A C8A H8A 119.9 . . ?
S1A C8A H8A 119.9 . . ?
N7 C9 C8 127.2(3) . . ?
N7 C9 H9 116.4 . . ?
C8 C9 H9 116.4 . . ?
N7A C9A C8A 126.7(3) . . ?
N7A C9A H9A 116.6 . . ?
C8A C9A H9A 116.6 . . ?
N7 C10 C11 112.1(3) . . ?
N7 C10 H10C 109.2 . . ?
C11 C10 H10C 109.2 . . ?
N7 C10 H10D 109.2 . . ?
C11 C10 H10D 109.2 . . ?
H10C C10 H10D 107.9 . . ?
N7A C10A C11A 112.5(3) . . ?
N7A C10A H10A 109.1 . . ?
C11A C10A H10A 109.1 . . ?
N7A C10A H10B 109.1 . . ?
C11A C10A H10B 109.1 . . ?
H10A C10A H10B 107.8 . . ?
C10 C11 H11D 109.5 . . ?
C10 C11 H11E 109.5 . . ?
H11D C11 H11E 109.5 . . ?
C10 C11 H11F 109.5 . . ?
H11D C11 H11F 109.5 . . ?
H11E C11 H11F 109.5 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
N7 C12 C13 113.1(3) . . ?
N7 C12 H12C 109.0 . . ?
C13 C12 H12C 109.0 . . ?
N7 C12 H12D 109.0 . . ?
C13 C12 H12D 109.0 . . ?
H12C C12 H12D 107.8 . . ?
N7A C12A C13A 112.3(3) . . ?
N7A C12A H12A 109.2 . . ?
C13A C12A H12A 109.2 . . ?
N7A C12A H12B 109.2 . . ?
C13A C12A H12B 109.2 . . ?
H12A C12A H12B 107.9 . . ?
C12 C13 H13D 109.5 . . ?
C12 C13 H13E 109.5 . . ?
H13D C13 H13E 109.5 . . ?
C12 C13 H13F 109.5 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
C12A C13A H13A 109.5 . . ?
C12A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C12A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C1 C6 -30.9(3) . . . . ?
O1 S1 C1 C6 -158.5(2) . . . . ?
C8 S1 C1 C6 84.4(3) . . . . ?
O2 S1 C1 C2 150.4(2) . . . . ?
O1 S1 C1 C2 22.8(3) . . . . ?
C8 S1 C1 C2 -94.3(3) . . . . ?
O2A S1A C1A C6A -26.7(3) . . . . ?
O1A S1A C1A C6A -154.3(2) . . . . ?
C8A S1A C1A C6A 88.8(3) . . . . ?
O2A S1A C1A C2A 157.8(2) . . . . ?
O1A S1A C1A C2A 30.2(3) . . . . ?
C8A S1A C1A C2A -86.7(3) . . . . ?
C6 C1 C2 C3 1.8(4) . . . . ?
S1 C1 C2 C3 -179.4(2) . . . . ?
C6A C1A C2A C3A -0.6(4) . . . . ?
S1A C1A C2A C3A 174.9(2) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C1A C2A C3A C4A -0.3(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C2 C3 C4 C7 178.5(3) . . . . ?
C2A C3A C4A C5A 1.0(5) . . . . ?
C2A C3A C4A C7A -178.7(3) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C7 C4 C5 C6 -178.6(3) . . . . ?
C3A C4A C5A C6A -0.9(5) . . . . ?
C7A C4A C5A C6A 178.8(3) . . . . ?
C4 C5 C6 C1 1.0(5) . . . . ?
C2 C1 C6 C5 -2.0(4) . . . . ?
S1 C1 C6 C5 179.3(2) . . . . ?
C4A C5A C6A C1A 0.1(5) . . . . ?
C2A C1A C6A C5A 0.7(4) . . . . ?
S1A C1A C6A C5A -174.8(2) . . . . ?
O2 S1 C8 C9 -136.8(3) . . . . ?
O1 S1 C8 C9 -5.7(3) . . . . ?
C1 S1 C8 C9 109.2(3) . . . . ?
O2A S1A C8A C9A -143.1(2) . . . . ?
O1A S1A C8A C9A -12.5(3) . . . . ?
C1A S1A C8A C9A 102.7(3) . . . . ?
C10 N7 C9 C8 1.7(5) . . . . ?
C12 N7 C9 C8 179.1(3) . . . . ?
S1 C8 C9 N7 175.3(3) . . . . ?
C12A N7A C9A C8A -173.3(3) . . . . ?
C10A N7A C9A C8A 0.0(5) . . . . ?
S1A C8A C9A N7A 177.0(2) . . . . ?
C9 N7 C10 C11 95.0(4) . . . . ?
C12 N7 C10 C11 -82.5(4) . . . . ?
C9A N7A C10A C11A 82.8(4) . . . . ?
C12A N7A C10A C11A -103.6(3) . . . . ?
C9 N7 C12 C13 104.2(3) . . . . ?
C10 N7 C12 C13 -78.3(4) . . . . ?
C9A N7A C12A C13A 91.8(3) . . . . ?
C10A N7A C12A C13A -81.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 997483'
