# 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
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# 
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#  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.
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data_Compound5bb
#data_gc352 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H56 Cl2 N2 O12 S2'
_chemical_formula_sum            'C38 H56 Cl2 N2 O12 S2'
_chemical_formula_weight         867.87
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_HALL  'P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.2925(5)
_cell_length_b                   22.0931(18)
_cell_length_c                   15.8946(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.1980(10)
_cell_angle_gamma                90.00
_cell_volume                     2209.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8351
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_process_details   
;
SADABS G.M Sheldrick, University of 
Gẗtingen, Germany, 2008.
;

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37001
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0650
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         30.09
_reflns_number_total             12989
_reflns_number_gt                12308
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0523P)²+4.9345P] where P=(Fo²+2Fc²)/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   0.06(7)
_refine_ls_number_reflns         12989
_refine_ls_number_parameters     525
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1875
_refine_ls_wR_factor_gt          0.1860
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_restrained_S_all      1.177
_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
Cl1 Cl 0.64464(16) 0.61567(5) -0.04205(6) 0.0269(2) Uani 1 1 d . . .
S1 S 0.93206(16) 0.43521(4) 0.15071(6) 0.02157(18) Uani 1 1 d . . .
O1 O 0.7820(6) 0.44652(15) 0.22091(19) 0.0300(7) Uani 1 1 d . . .
N1 N 0.9781(5) 0.49772(14) 0.0973(2) 0.0185(6) Uani 1 1 d D . .
H1N H 1.074(8) 0.514(2) 0.133(3) 0.028 Uiso 1 1 d D . .
C1 C 0.8834(6) 0.57758(19) -0.0011(2) 0.0216(7) Uani 1 1 d . . .
O2 O 0.8991(4) 0.59167(12) 0.20134(16) 0.0186(5) Uani 1 1 d . . .
C2 C 0.8056(6) 0.53848(17) 0.0733(2) 0.0172(6) Uani 1 1 d . . .
H2A H 0.6848 0.5131 0.0525 0.021 Uiso 1 1 calc R . .
Cl2 Cl 0.13251(17) 0.40913(4) 0.78835(6) 0.0265(2) Uani 1 1 d . . .
S2 S 0.41045(15) 0.58854(4) 0.59473(6) 0.01949(17) Uani 1 1 d . . .
N2 N 0.4603(5) 0.52379(14) 0.6443(2) 0.0171(6) Uani 1 1 d D . .
H2N H 0.586(7) 0.510(2) 0.623(3) 0.026 Uiso 1 1 d D . .
O3 O 1.0653(4) 0.65194(13) 0.28375(17) 0.0210(5) Uani 1 1 d . . .
C3 C 0.7788(6) 0.39517(17) 0.0736(2) 0.0200(7) Uani 1 1 d . . .
O4 O 0.7462(5) 0.68187(13) 0.23053(19) 0.0254(6) Uani 1 1 d . . .
C4 C 0.5758(7) 0.3762(2) 0.0929(3) 0.0298(9) Uani 1 1 d . . .
H4A H 0.5106 0.3892 0.1436 0.036 Uiso 1 1 calc R . .
O5 O 0.3961(5) 0.52374(15) 0.15516(19) 0.0274(6) Uani 1 1 d . . .
C5 C 0.4670(8) 0.3382(2) 0.0384(3) 0.0344(10) Uani 1 1 d . . .
H5A H 0.3263 0.3260 0.0518 0.041 Uiso 1 1 calc R . .
O6 O 0.5475(4) 0.55492(13) 0.27557(17) 0.0207(5) Uani 1 1 d . . .
C6 C 0.5589(8) 0.3175(2) -0.0350(3) 0.0333(10) Uani 1 1 d . . .
C7 C 0.7625(8) 0.33807(19) -0.0552(3) 0.0293(9) Uani 1 1 d . . .
H7A H 0.8267 0.3255 -0.1063 0.035 Uiso 1 1 calc R . .
O7 O 0.2551(5) 0.58154(14) 0.52571(17) 0.0273(6) Uani 1 1 d . . .
C8 C 0.8720(7) 0.37671(19) -0.0014(3) 0.0247(8) Uani 1 1 d . . .
H8A H 1.0103 0.3905 -0.0158 0.030 Uiso 1 1 calc R . .
O8 O 0.3766(4) 0.42840(12) 0.54235(17) 0.0190(5) Uani 1 1 d . . .
C9 C 0.4422(11) 0.2742(3) -0.0922(4) 0.0468(14) Uani 1 1 d . . .
H9A H 0.3375 0.2513 -0.0595 0.070 Uiso 1 1 calc R . .
H9B H 0.5439 0.2460 -0.1176 0.070 Uiso 1 1 calc R . .
H9C H 0.3693 0.2970 -0.1367 0.070 Uiso 1 1 calc R . .
O9 O 0.5244(4) 0.37131(13) 0.45136(18) 0.0233(6) Uani 1 1 d . . .
C10 C 0.7229(5) 0.57727(17) 0.1471(2) 0.0171(6) Uani 1 1 d . . .
H10A H 0.6686 0.6161 0.1231 0.021 Uiso 1 1 calc R . .
O10 O 0.1997(5) 0.34400(13) 0.50187(19) 0.0253(6) Uani 1 1 d . . .
C11 C 0.8868(6) 0.64669(17) 0.2392(2) 0.0183(7) Uani 1 1 d . . .
O11 O -0.1243(5) 0.49654(15) 0.58749(19) 0.0275(6) Uani 1 1 d . . .
C12 C 1.1010(7) 0.70625(18) 0.3365(3) 0.0230(7) Uani 1 1 d . . .
O12 O 0.0369(4) 0.47180(13) 0.46647(17) 0.0220(5) Uani 1 1 d . . .
C13 C 0.9519(8) 0.7035(3) 0.4104(3) 0.0370(11) Uani 1 1 d . . .
H13A H 0.8059 0.7102 0.3909 0.056 Uiso 1 1 calc R . .
H13B H 0.9906 0.7348 0.4513 0.056 Uiso 1 1 calc R . .
H13C H 0.9621 0.6636 0.4370 0.056 Uiso 1 1 calc R . .
C14 C 1.0796(12) 0.7636(3) 0.2857(4) 0.059(2) Uani 1 1 d . . .
H14A H 0.9299 0.7700 0.2710 0.088 Uiso 1 1 calc R . .
H14B H 1.1638 0.7601 0.2342 0.088 Uiso 1 1 calc R . .
H14C H 1.1312 0.7980 0.3189 0.088 Uiso 1 1 calc R . .
C15 C 1.3313(7) 0.6968(2) 0.3649(3) 0.0331(10) Uani 1 1 d . . .
H15A H 1.4241 0.6960 0.3155 0.050 Uiso 1 1 calc R . .
H15B H 1.3431 0.6583 0.3952 0.050 Uiso 1 1 calc R . .
H15C H 1.3740 0.7301 0.4021 0.050 Uiso 1 1 calc R . .
C16 C 0.5392(6) 0.54710(18) 0.1935(2) 0.0204(7) Uani 1 1 d . . .
C17 C 0.3698(7) 0.52801(19) 0.3217(3) 0.0243(8) Uani 1 1 d . . .
H17A H 0.3942 0.5325 0.3823 0.036 Uiso 1 1 calc R . .
H17B H 0.3588 0.4849 0.3077 0.036 Uiso 1 1 calc R . .
H17C H 0.2375 0.5486 0.3060 0.036 Uiso 1 1 calc R . .
C18 C 0.9674(7) 0.5389(2) -0.0730(3) 0.0282(8) Uani 1 1 d . . .
H18A H 1.1094 0.5239 -0.0586 0.042 Uiso 1 1 calc R . .
H18B H 0.9751 0.5634 -0.1243 0.042 Uiso 1 1 calc R . .
H18C H 0.8716 0.5046 -0.0824 0.042 Uiso 1 1 calc R . .
C19 C 1.0413(7) 0.6269(2) 0.0233(3) 0.0270(8) Uani 1 1 d . . .
H19A H 1.1652 0.6085 0.0507 0.040 Uiso 1 1 calc R . .
H19B H 0.9735 0.6553 0.0622 0.040 Uiso 1 1 calc R . .
H19C H 1.0869 0.6486 -0.0273 0.040 Uiso 1 1 calc R . .
C20 C 0.3723(6) 0.44493(16) 0.7453(2) 0.0179(6) Uani 1 1 d . . .
C21 C 0.2902(5) 0.48322(16) 0.6692(2) 0.0158(6) Uani 1 1 d . . .
H21A H 0.1701 0.5088 0.6899 0.019 Uiso 1 1 calc R . .
C22 C 0.2675(6) 0.62618(16) 0.6769(2) 0.0189(7) Uani 1 1 d . . .
C23 C 0.0634(6) 0.64576(17) 0.6629(3) 0.0220(7) Uani 1 1 d . . .
H23A H -0.0113 0.6332 0.6139 0.026 Uiso 1 1 calc R . .
C24 C -0.0337(6) 0.68390(18) 0.7204(3) 0.0222(7) Uani 1 1 d . . .
H24A H -0.1751 0.6973 0.7106 0.027 Uiso 1 1 calc R . .
C25 C 0.0740(7) 0.70273(17) 0.7924(3) 0.0220(7) Uani 1 1 d . . .
C26 C 0.2799(7) 0.68163(18) 0.8069(3) 0.0234(7) Uani 1 1 d . . .
H26A H 0.3540 0.6934 0.8564 0.028 Uiso 1 1 calc R . .
C27 C 0.3764(6) 0.64364(17) 0.7495(2) 0.0192(7) Uani 1 1 d . . .
H27A H 0.5168 0.6294 0.7594 0.023 Uiso 1 1 calc R . .
C28 C -0.0297(8) 0.74673(19) 0.8530(3) 0.0301(9) Uani 1 1 d . . .
H28A H -0.0723 0.7834 0.8226 0.045 Uiso 1 1 calc R . .
H28B H 0.0715 0.7574 0.8976 0.045 Uiso 1 1 calc R . .
H28C H -0.1554 0.7278 0.8780 0.045 Uiso 1 1 calc R . .
C29 C 0.2036(5) 0.44368(17) 0.5968(2) 0.0177(6) Uani 1 1 d . . .
H29A H 0.1470 0.4054 0.6216 0.021 Uiso 1 1 calc R . .
C30 C 0.3516(6) 0.37696(17) 0.4969(2) 0.0186(7) Uani 1 1 d . . .
C31 C 0.5383(7) 0.32260(18) 0.3864(3) 0.0236(7) Uani 1 1 d . . .
C32 C 0.5047(10) 0.2606(2) 0.4243(3) 0.0395(12) Uani 1 1 d . . .
H32A H 0.3555 0.2562 0.4407 0.059 Uiso 1 1 calc R . .
H32B H 0.5958 0.2560 0.4740 0.059 Uiso 1 1 calc R . .
H32C H 0.5409 0.2295 0.3828 0.059 Uiso 1 1 calc R . .
C33 C 0.3826(8) 0.3362(2) 0.3177(3) 0.0303(9) Uani 1 1 d . . .
H33A H 0.2384 0.3367 0.3408 0.045 Uiso 1 1 calc R . .
H33B H 0.3924 0.3051 0.2740 0.045 Uiso 1 1 calc R . .
H33C H 0.4149 0.3759 0.2932 0.045 Uiso 1 1 calc R . .
C34 C 0.7658(8) 0.3306(2) 0.3554(3) 0.0352(10) Uani 1 1 d . . .
H34A H 0.7834 0.3716 0.3327 0.053 Uiso 1 1 calc R . .
H34B H 0.7953 0.3009 0.3113 0.053 Uiso 1 1 calc R . .
H34C H 0.8648 0.3246 0.4024 0.053 Uiso 1 1 calc R . .
C35 C 0.0219(6) 0.47491(17) 0.5490(2) 0.0187(7) Uani 1 1 d . . .
C36 C -0.1357(6) 0.5000(2) 0.4204(3) 0.0247(8) Uani 1 1 d . . .
H36A H -0.1334 0.4862 0.3618 0.037 Uiso 1 1 calc R . .
H36B H -0.1191 0.5441 0.4222 0.037 Uiso 1 1 calc R . .
H36C H -0.2714 0.4887 0.4461 0.037 Uiso 1 1 calc R . .
C37 C 0.5221(7) 0.39432(19) 0.7199(3) 0.0260(8) Uani 1 1 d . . .
H37A H 0.6456 0.4115 0.6910 0.039 Uiso 1 1 calc R . .
H37B H 0.4479 0.3663 0.6820 0.039 Uiso 1 1 calc R . .
H37C H 0.5694 0.3724 0.7702 0.039 Uiso 1 1 calc R . .
C38 C 0.4633(8) 0.4847(2) 0.8139(3) 0.0282(8) Uani 1 1 d . . .
H38A H 0.6000 0.5013 0.7955 0.042 Uiso 1 1 calc R . .
H38B H 0.4843 0.4606 0.8650 0.042 Uiso 1 1 calc R . .
H38C H 0.3647 0.5180 0.8255 0.042 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
Cl1 C1 1.839(4) . ?
S1 O1 1.485(3) . ?
S1 N1 1.648(3) . ?
S1 C3 1.791(4) . ?
N1 C2 1.460(5) . ?
N1 H1N 0.90(4) . ?
C1 C18 1.523(6) . ?
C1 C19 1.524(6) . ?
C1 C2 1.544(5) . ?
O2 C11 1.358(4) . ?
O2 C10 1.438(4) . ?
C2 C10 1.546(5) . ?
C2 H2A 1.0000 . ?
Cl2 C20 1.838(4) . ?
S2 O7 1.475(3) . ?
S2 N2 1.663(3) . ?
S2 C22 1.793(4) . ?
N2 C21 1.452(4) . ?
N2 H2N 0.91(4) . ?
O3 C11 1.331(4) . ?
O3 C12 1.481(5) . ?
C3 C4 1.380(6) . ?
C3 C8 1.391(5) . ?
O4 C11 1.185(5) . ?
C4 C5 1.387(7) . ?
C4 H4A 0.9500 . ?
O5 C16 1.202(5) . ?
C5 C6 1.381(7) . ?
C5 H5A 0.9500 . ?
O6 C16 1.317(5) . ?
O6 C17 1.466(5) . ?
C6 C7 1.397(7) . ?
C6 C9 1.510(7) . ?
C7 C8 1.390(6) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
O8 C30 1.356(4) . ?
O8 C29 1.434(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O9 C30 1.314(4) . ?
O9 C31 1.494(5) . ?
C10 C16 1.526(5) . ?
C10 H10A 1.0000 . ?
O10 C30 1.205(5) . ?
O11 C35 1.205(5) . ?
C12 C13 1.506(6) . ?
C12 C14 1.508(7) . ?
C12 C15 1.530(6) . ?
O12 C35 1.317(5) . ?
O12 C36 1.448(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C38 1.511(5) . ?
C20 C37 1.518(5) . ?
C20 C21 1.562(5) . ?
C21 C29 1.543(5) . ?
C21 H21A 1.0000 . ?
C22 C23 1.373(5) . ?
C22 C27 1.393(5) . ?
C23 C24 1.387(6) . ?
C23 H23A 0.9500 . ?
C24 C25 1.391(6) . ?
C24 H24A 0.9500 . ?
C25 C26 1.396(6) . ?
C25 C28 1.518(5) . ?
C26 C27 1.382(5) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C35 1.535(5) . ?
C29 H29A 1.0000 . ?
C31 C33 1.495(6) . ?
C31 C32 1.511(6) . ?
C31 C34 1.526(6) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 111.08(18) . . ?
O1 S1 C3 104.79(19) . . ?
N1 S1 C3 98.98(17) . . ?
C2 N1 S1 121.3(3) . . ?
C2 N1 H1N 114(4) . . ?
S1 N1 H1N 98(4) . . ?
C18 C1 C19 111.4(3) . . ?
C18 C1 C2 111.9(3) . . ?
C19 C1 C2 114.4(3) . . ?
C18 C1 Cl1 106.0(3) . . ?
C19 C1 Cl1 107.1(3) . . ?
C2 C1 Cl1 105.5(3) . . ?
C11 O2 C10 114.7(3) . . ?
N1 C2 C1 107.9(3) . . ?
N1 C2 C10 113.3(3) . . ?
C1 C2 C10 112.3(3) . . ?
N1 C2 H2A 107.7 . . ?
C1 C2 H2A 107.7 . . ?
C10 C2 H2A 107.7 . . ?
O7 S2 N2 112.71(17) . . ?
O7 S2 C22 104.94(18) . . ?
N2 S2 C22 98.49(16) . . ?
C21 N2 S2 121.5(2) . . ?
C21 N2 H2N 123(4) . . ?
S2 N2 H2N 106(4) . . ?
C11 O3 C12 119.9(3) . . ?
C4 C3 C8 119.7(4) . . ?
C4 C3 S1 119.6(3) . . ?
C8 C3 S1 120.2(3) . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 121.4(4) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C16 O6 C17 114.5(3) . . ?
C5 C6 C7 118.3(4) . . ?
C5 C6 C9 120.9(5) . . ?
C7 C6 C9 120.8(5) . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C7 C8 C3 119.8(4) . . ?
C7 C8 H8A 120.1 . . ?
C3 C8 H8A 120.1 . . ?
C30 O8 C29 115.6(3) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C30 O9 C31 120.0(3) . . ?
O2 C10 C16 113.1(3) . . ?
O2 C10 C2 108.5(3) . . ?
C16 C10 C2 112.5(3) . . ?
O2 C10 H10A 107.5 . . ?
C16 C10 H10A 107.5 . . ?
C2 C10 H10A 107.5 . . ?
O4 C11 O3 129.3(4) . . ?
O4 C11 O2 125.4(3) . . ?
O3 C11 O2 105.3(3) . . ?
O3 C12 C13 108.3(3) . . ?
O3 C12 C14 111.3(4) . . ?
C13 C12 C14 113.4(5) . . ?
O3 C12 C15 101.4(3) . . ?
C13 C12 C15 110.9(4) . . ?
C14 C12 C15 110.8(4) . . ?
C35 O12 C36 115.1(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O5 C16 O6 125.8(4) . . ?
O5 C16 C10 120.7(3) . . ?
O6 C16 C10 113.2(3) . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 C18 H18A 109.5 . . ?
C1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 C19 H19A 109.5 . . ?
C1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C38 C20 C37 112.7(4) . . ?
C38 C20 C21 111.5(3) . . ?
C37 C20 C21 113.4(3) . . ?
C38 C20 Cl2 106.9(3) . . ?
C37 C20 Cl2 107.1(3) . . ?
C21 C20 Cl2 104.6(2) . . ?
N2 C21 C29 113.9(3) . . ?
N2 C21 C20 107.6(3) . . ?
C29 C21 C20 112.7(3) . . ?
N2 C21 H21A 107.4 . . ?
C29 C21 H21A 107.4 . . ?
C20 C21 H21A 107.4 . . ?
C23 C22 C27 120.3(3) . . ?
C23 C22 S2 119.9(3) . . ?
C27 C22 S2 119.0(3) . . ?
C22 C23 C24 119.9(4) . . ?
C22 C23 H23A 120.1 . . ?
C24 C23 H23A 120.1 . . ?
C23 C24 C25 120.6(4) . . ?
C23 C24 H24A 119.7 . . ?
C25 C24 H24A 119.7 . . ?
C24 C25 C26 119.0(4) . . ?
C24 C25 C28 120.3(4) . . ?
C26 C25 C28 120.7(4) . . ?
C27 C26 C25 120.3(4) . . ?
C27 C26 H26A 119.9 . . ?
C25 C26 H26A 119.9 . . ?
C26 C27 C22 119.9(4) . . ?
C26 C27 H27A 120.1 . . ?
C22 C27 H27A 120.1 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O8 C29 C35 111.9(3) . . ?
O8 C29 C21 108.4(3) . . ?
C35 C29 C21 112.1(3) . . ?
O8 C29 H29A 108.1 . . ?
C35 C29 H29A 108.1 . . ?
C21 C29 H29A 108.1 . . ?
O10 C30 O9 129.6(4) . . ?
O10 C30 O8 124.2(3) . . ?
O9 C30 O8 106.2(3) . . ?
O9 C31 C33 108.7(3) . . ?
O9 C31 C32 111.6(3) . . ?
C33 C31 C32 112.4(4) . . ?
O9 C31 C34 101.3(3) . . ?
C33 C31 C34 110.8(4) . . ?
C32 C31 C34 111.5(4) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O11 C35 O12 125.8(4) . . ?
O11 C35 C29 119.7(3) . . ?
O12 C35 C29 114.4(3) . . ?
O12 C36 H36A 109.5 . . ?
O12 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O12 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C20 C37 H37A 109.5 . . ?
C20 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C20 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C20 C38 H38A 109.5 . . ?
C20 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C20 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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
O1 S1 N1 C2 -44.5(3) . . . . ?
C3 S1 N1 C2 65.2(3) . . . . ?
S1 N1 C2 C1 -159.2(3) . . . . ?
S1 N1 C2 C10 75.8(4) . . . . ?
C18 C1 C2 N1 53.6(4) . . . . ?
C19 C1 C2 N1 -74.2(4) . . . . ?
Cl1 C1 C2 N1 168.4(2) . . . . ?
C18 C1 C2 C10 179.2(3) . . . . ?
C19 C1 C2 C10 51.4(4) . . . . ?
Cl1 C1 C2 C10 -66.0(3) . . . . ?
O7 S2 N2 C21 -45.5(3) . . . . ?
C22 S2 N2 C21 64.7(3) . . . . ?
O1 S1 C3 C4 -7.4(4) . . . . ?
N1 S1 C3 C4 -122.1(4) . . . . ?
O1 S1 C3 C8 -179.5(3) . . . . ?
N1 S1 C3 C8 65.8(4) . . . . ?
C8 C3 C4 C5 1.0(7) . . . . ?
S1 C3 C4 C5 -171.1(4) . . . . ?
C3 C4 C5 C6 1.2(7) . . . . ?
C4 C5 C6 C7 -2.7(7) . . . . ?
C4 C5 C6 C9 177.5(5) . . . . ?
C5 C6 C7 C8 2.1(7) . . . . ?
C9 C6 C7 C8 -178.2(5) . . . . ?
C6 C7 C8 C3 0.1(7) . . . . ?
C4 C3 C8 C7 -1.7(6) . . . . ?
S1 C3 C8 C7 170.4(3) . . . . ?
C11 O2 C10 C16 -87.9(4) . . . . ?
C11 O2 C10 C2 146.7(3) . . . . ?
N1 C2 C10 O2 34.7(4) . . . . ?
C1 C2 C10 O2 -87.9(3) . . . . ?
N1 C2 C10 C16 -91.1(4) . . . . ?
C1 C2 C10 C16 146.3(3) . . . . ?
C12 O3 C11 O4 4.5(6) . . . . ?
C12 O3 C11 O2 -177.5(3) . . . . ?
C10 O2 C11 O4 0.0(5) . . . . ?
C10 O2 C11 O3 -178.1(3) . . . . ?
C11 O3 C12 C13 70.7(5) . . . . ?
C11 O3 C12 C14 -54.7(5) . . . . ?
C11 O3 C12 C15 -172.5(3) . . . . ?
C17 O6 C16 O5 4.6(6) . . . . ?
C17 O6 C16 C10 178.3(3) . . . . ?
O2 C10 C16 O5 -168.0(4) . . . . ?
C2 C10 C16 O5 -44.7(5) . . . . ?
O2 C10 C16 O6 18.0(5) . . . . ?
C2 C10 C16 O6 141.3(3) . . . . ?
S2 N2 C21 C29 79.4(4) . . . . ?
S2 N2 C21 C20 -154.9(2) . . . . ?
C38 C20 C21 N2 51.5(4) . . . . ?
C37 C20 C21 N2 -77.0(4) . . . . ?
Cl2 C20 C21 N2 166.7(2) . . . . ?
C38 C20 C21 C29 178.0(3) . . . . ?
C37 C20 C21 C29 49.4(4) . . . . ?
Cl2 C20 C21 C29 -66.8(3) . . . . ?
O7 S2 C22 C23 -5.3(4) . . . . ?
N2 S2 C22 C23 -121.6(3) . . . . ?
O7 S2 C22 C27 -175.2(3) . . . . ?
N2 S2 C22 C27 68.5(3) . . . . ?
C27 C22 C23 C24 1.1(6) . . . . ?
S2 C22 C23 C24 -168.7(3) . . . . ?
C22 C23 C24 C25 0.2(6) . . . . ?
C23 C24 C25 C26 -1.4(6) . . . . ?
C23 C24 C25 C28 177.2(4) . . . . ?
C24 C25 C26 C27 1.4(6) . . . . ?
C28 C25 C26 C27 -177.2(4) . . . . ?
C25 C26 C27 C22 -0.2(6) . . . . ?
C23 C22 C27 C26 -1.1(6) . . . . ?
S2 C22 C27 C26 168.8(3) . . . . ?
C30 O8 C29 C35 -80.8(4) . . . . ?
C30 O8 C29 C21 155.1(3) . . . . ?
N2 C21 C29 O8 35.1(4) . . . . ?
C20 C21 C29 O8 -87.9(3) . . . . ?
N2 C21 C29 C35 -88.9(4) . . . . ?
C20 C21 C29 C35 148.1(3) . . . . ?
C31 O9 C30 O10 8.9(6) . . . . ?
C31 O9 C30 O8 -173.1(3) . . . . ?
C29 O8 C30 O10 -2.2(5) . . . . ?
C29 O8 C30 O9 179.6(3) . . . . ?
C30 O9 C31 C33 67.2(5) . . . . ?
C30 O9 C31 C32 -57.3(5) . . . . ?
C30 O9 C31 C34 -176.1(4) . . . . ?
C36 O12 C35 O11 3.2(6) . . . . ?
C36 O12 C35 C29 178.8(3) . . . . ?
O8 C29 C35 O11 -171.7(3) . . . . ?
C21 C29 C35 O11 -49.7(5) . . . . ?
O8 C29 C35 O12 12.3(4) . . . . ?
C21 C29 C35 O12 134.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.09
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.108
_database_code_depnum_ccdc_archive 'CCDC 977960'
#######################################################################
#
#                 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_Compound6dc
#data_mn28a

_audit_creation_date             2013-11-29T16:27:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H27 N O6 S'
_chemical_formula_sum            'C15 H27 N O6 S'
_chemical_formula_weight         349.44
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.2379(2)
_cell_length_b                   10.1214(2)
_cell_length_c                   19.9426(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1864.64(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2598
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.283
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_number            3998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.62
_diffrn_reflns_theta_max         27
_diffrn_reflns_theta_full        27
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             3998
_reflns_number_gt                3829
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0181P)²+0.6454P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3998
_refine_ls_number_parameters     215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0637
_refine_ls_wR_factor_gt          0.0622
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.031

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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 0.63838(4) 0.18426(4) 0.057119(18) 0.02441(8) Uani 1 1 d . . .
O1 O 0.79235(13) 0.14885(12) 0.04477(6) 0.0383(3) Uani 1 1 d . . .
O2 O 0.41913(11) -0.12263(10) 0.12793(5) 0.0221(2) Uani 1 1 d . . .
O3 O 0.22548(10) -0.21425(10) 0.09208(5) 0.0236(2) Uani 1 1 d . . .
O4 O 0.23948(11) -0.15930(10) 0.20277(5) 0.0257(2) Uani 1 1 d . . .
O5 O 0.69020(10) -0.19292(10) 0.25028(5) 0.0232(2) Uani 1 1 d . . .
O6 O 0.53311(12) -0.32616(11) 0.19642(6) 0.0293(2) Uani 1 1 d . . .
N1 N 0.58949(13) 0.13245(12) 0.13586(6) 0.0202(2) Uani 1 1 d . . .
C1 C 0.70833(16) 0.10125(14) 0.18362(7) 0.0228(3) Uani 1 1 d . . .
H1A H 0.8087 0.1216 0.1696 0.027 Uiso 1 1 calc R . .
H1B H 0.6889 0.1127 0.2321 0.027 Uiso 1 1 calc R . .
C2 C 0.63181(15) -0.00626(13) 0.14821(7) 0.0203(3) Uani 1 1 d . . .
H2 H 0.6873 -0.0498 0.1113 0.024 Uiso 1 1 calc R . .
C3 C 0.63406(16) 0.36403(14) 0.07201(7) 0.0229(3) Uani 1 1 d . . .
C4 C 0.48231(17) 0.40220(16) 0.09451(8) 0.0289(3) Uani 1 1 d . . .
H4A H 0.4638 0.3657 0.1392 0.043 Uiso 1 1 calc R . .
H4B H 0.4113 0.3668 0.0627 0.043 Uiso 1 1 calc R . .
H4C H 0.4742 0.4987 0.0961 0.043 Uiso 1 1 calc R . .
C5 C 0.6678(2) 0.42125(17) 0.00249(8) 0.0369(4) Uani 1 1 d . . .
H5A H 0.592 0.3947 -0.0292 0.055 Uiso 1 1 calc R . .
H5B H 0.7615 0.3878 -0.013 0.055 Uiso 1 1 calc R . .
H5C H 0.6713 0.5179 0.0052 0.055 Uiso 1 1 calc R . .
C6 C 0.74944(18) 0.40322(15) 0.12272(9) 0.0312(4) Uani 1 1 d . . .
H6A H 0.7553 0.4998 0.1253 0.047 Uiso 1 1 calc R . .
H6B H 0.8433 0.3675 0.1087 0.047 Uiso 1 1 calc R . .
H6C H 0.724 0.3676 0.1669 0.047 Uiso 1 1 calc R . .
C7 C 0.51800(15) -0.08981(14) 0.18079(7) 0.0194(3) Uani 1 1 d . . .
H7 H 0.4673 -0.0387 0.2167 0.023 Uiso 1 1 calc R . .
C8 C 0.28743(15) -0.16655(13) 0.14712(7) 0.0193(3) Uani 1 1 d . . .
C9 C 0.08570(15) -0.28584(16) 0.09705(8) 0.0258(3) Uani 1 1 d . . .
C10 C 0.09996(18) -0.39795(17) 0.14713(10) 0.0368(4) Uani 1 1 d . . .
H10A H 0.1896 -0.4468 0.1384 0.055 Uiso 1 1 calc R . .
H10B H 0.017 -0.4577 0.1426 0.055 Uiso 1 1 calc R . .
H10C H 0.1024 -0.3618 0.1927 0.055 Uiso 1 1 calc R . .
C11 C -0.03437(17) -0.19026(18) 0.11486(9) 0.0329(4) Uani 1 1 d . . .
H11A H -0.0176 -0.1548 0.1599 0.049 Uiso 1 1 calc R . .
H11B H -0.1276 -0.2365 0.1138 0.049 Uiso 1 1 calc R . .
H11C H -0.0357 -0.1176 0.0824 0.049 Uiso 1 1 calc R . .
C12 C 0.0682(2) -0.3381(2) 0.02622(9) 0.0434(5) Uani 1 1 d . . .
H12A H 0.0661 -0.2639 -0.0054 0.065 Uiso 1 1 calc R . .
H12B H -0.0225 -0.3879 0.0229 0.065 Uiso 1 1 calc R . .
H12C H 0.1497 -0.3962 0.0153 0.065 Uiso 1 1 calc R . .
C13 C 0.57912(15) -0.21832(14) 0.20925(7) 0.0205(3) Uani 1 1 d . . .
C14 C 0.75432(16) -0.30926(15) 0.28245(8) 0.0263(3) Uani 1 1 d . . .
H14A H 0.7841 -0.3745 0.2481 0.032 Uiso 1 1 calc R . .
H14B H 0.6831 -0.3516 0.3127 0.032 Uiso 1 1 calc R . .
C15 C 0.88351(17) -0.26334(17) 0.32163(9) 0.0319(4) Uani 1 1 d . . .
H15A H 0.953 -0.2213 0.2912 0.048 Uiso 1 1 calc R . .
H15B H 0.9293 -0.3392 0.3436 0.048 Uiso 1 1 calc R . .
H15C H 0.8526 -0.1995 0.3557 0.048 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4873(12) . ?
S1 N1 1.7159(12) . ?
S1 C3 1.8441(15) . ?
O2 C8 1.3506(16) . ?
O2 C7 1.4338(16) . ?
O3 C8 1.3287(16) . ?
O3 C9 1.4840(17) . ?
O4 C8 1.1971(17) . ?
O5 C13 1.3374(17) . ?
O5 C14 1.4660(17) . ?
O6 C13 1.1990(18) . ?
N1 C2 1.4781(17) . ?
N1 C1 1.4874(18) . ?
C1 C2 1.4772(19) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C2 C7 1.4975(19) . ?
C2 H2 1 . ?
C3 C4 1.522(2) . ?
C3 C6 1.522(2) . ?
C3 C5 1.534(2) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 C13 1.5273(19) . ?
C7 H7 1 . ?
C9 C11 1.514(2) . ?
C9 C12 1.517(2) . ?
C9 C10 1.517(2) . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C14 C15 1.500(2) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 109.24(7) . . ?
O1 S1 C3 106.57(7) . . ?
N1 S1 C3 98.54(6) . . ?
C8 O2 C7 116.21(11) . . ?
C8 O3 C9 119.80(11) . . ?
C13 O5 C14 115.05(11) . . ?
C2 N1 C1 59.75(9) . . ?
C2 N1 S1 111.91(9) . . ?
C1 N1 S1 117.17(9) . . ?
C2 C1 N1 59.81(9) . . ?
C2 C1 H1A 117.8 . . ?
N1 C1 H1A 117.8 . . ?
C2 C1 H1B 117.8 . . ?
N1 C1 H1B 117.8 . . ?
H1A C1 H1B 114.9 . . ?
C1 C2 N1 60.43(9) . . ?
C1 C2 C7 123.00(12) . . ?
N1 C2 C7 115.02(11) . . ?
C1 C2 H2 115.5 . . ?
N1 C2 H2 115.5 . . ?
C7 C2 H2 115.5 . . ?
C4 C3 C6 112.53(13) . . ?
C4 C3 C5 110.95(13) . . ?
C6 C3 C5 111.09(13) . . ?
C4 C3 S1 108.53(10) . . ?
C6 C3 S1 110.43(10) . . ?
C5 C3 S1 102.86(10) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
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 . . ?
O2 C7 C2 105.02(11) . . ?
O2 C7 C13 108.15(11) . . ?
C2 C7 C13 112.49(12) . . ?
O2 C7 H7 110.3 . . ?
C2 C7 H7 110.3 . . ?
C13 C7 H7 110.3 . . ?
O4 C8 O3 128.95(13) . . ?
O4 C8 O2 125.16(13) . . ?
O3 C8 O2 105.87(11) . . ?
O3 C9 C11 109.95(12) . . ?
O3 C9 C12 101.58(12) . . ?
C11 C9 C12 111.29(14) . . ?
O3 C9 C10 109.48(12) . . ?
C11 C9 C10 112.77(14) . . ?
C12 C9 C10 111.19(15) . . ?
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 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 C13 O5 125.28(13) . . ?
O6 C13 C7 124.39(13) . . ?
O5 C13 C7 110.33(12) . . ?
O5 C14 C15 107.49(12) . . ?
O5 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
O5 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O1 S1 N1 C2 -48.77(11) . . . . ?
C3 S1 N1 C2 -159.74(10) . . . . ?
O1 S1 N1 C1 17.41(12) . . . . ?
C3 S1 N1 C1 -93.56(11) . . . . ?
S1 N1 C1 C2 -100.74(11) . . . . ?
N1 C1 C2 C7 -102.21(14) . . . . ?
S1 N1 C2 C1 109.58(11) . . . . ?
C1 N1 C2 C7 115.23(14) . . . . ?
S1 N1 C2 C7 -135.19(10) . . . . ?
O1 S1 C3 C4 -172.17(10) . . . . ?
N1 S1 C3 C4 -59.07(11) . . . . ?
O1 S1 C3 C6 -48.39(12) . . . . ?
N1 S1 C3 C6 64.71(12) . . . . ?
O1 S1 C3 C5 70.23(12) . . . . ?
N1 S1 C3 C5 -176.67(11) . . . . ?
C8 O2 C7 C2 -162.57(11) . . . . ?
C8 O2 C7 C13 77.11(14) . . . . ?
C1 C2 C7 O2 147.84(13) . . . . ?
N1 C2 C7 O2 78.09(14) . . . . ?
C1 C2 C7 C13 -94.77(15) . . . . ?
N1 C2 C7 C13 -164.52(11) . . . . ?
C9 O3 C8 O4 -9.0(2) . . . . ?
C9 O3 C8 O2 172.49(11) . . . . ?
C7 O2 C8 O4 13.11(19) . . . . ?
C7 O2 C8 O3 -168.33(11) . . . . ?
C8 O3 C9 C11 69.92(16) . . . . ?
C8 O3 C9 C12 -172.13(14) . . . . ?
C8 O3 C9 C10 -54.49(17) . . . . ?
C14 O5 C13 O6 -1.9(2) . . . . ?
C14 O5 C13 C7 177.96(11) . . . . ?
O2 C7 C13 O6 -11.05(19) . . . . ?
C2 C7 C13 O6 -126.57(15) . . . . ?
O2 C7 C13 O5 169.07(11) . . . . ?
C2 C7 C13 O5 53.55(16) . . . . ?
C13 O5 C14 C15 175.42(12) . . . . ?

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 977961'
#######################################################################
#
#                 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_Compound7ac
#data_gc348 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 Cl N O4 S'
_chemical_formula_sum            'C12 H24 Cl N O4 S'
_chemical_formula_weight         313.83
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_H-M   P3(1)
_symmetry_space_group_name_HALL  ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   9.4099(9)
_cell_length_b                   9.4099(9)
_cell_length_c                   31.116(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2386.1(4)
_cell_formula_units_Z            6
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9653
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      31.48

_exptl_crystal_description       'irregular prism'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.51
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8238
_exptl_absorpt_correction_T_max  0.8300
_exptl_absorpt_process_details   
;
SADABS G.M Sheldrick, University of 
Gẗtingen, Germany, 2008.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41013
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         31.48
_reflns_number_total             10576
_reflns_number_gt                10532
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0319P)²+1.2559P] where P=(Fo²+2Fc²)/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   0.08(4)
_refine_ls_number_reflns         10576
_refine_ls_number_parameters     363
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.244
_refine_ls_restrained_S_all      1.244
_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
Cl1 Cl -0.33604(5) 0.63845(6) 0.115250(15) 0.02067(9) Uani 1 1 d . . .
S1 S -0.06353(5) 0.53296(5) 0.139018(13) 0.01334(7) Uani 1 1 d . . .
O1 O -0.19710(16) 0.37672(16) 0.15757(5) 0.0190(2) Uani 1 1 d . . .
N1 N -0.01697(18) 0.68711(18) 0.17282(5) 0.0137(2) Uani 1 1 d . . .
H1 H -0.027(3) 0.664(3) 0.1982(9) 0.016 Uiso 1 1 d . . .
C1 C -0.2469(2) 0.7562(2) 0.16475(6) 0.0151(3) Uani 1 1 d . . .
O2 O 0.00124(17) 0.90412(19) 0.23642(4) 0.0218(3) Uani 1 1 d . . .
H2A H 0.0857 0.9523 0.2518 0.033 Uiso 1 1 calc R . .
N2 N 0.50386(19) 0.16426(18) 0.29487(5) 0.0134(2) Uani 1 1 d . . .
C2 C -0.06159(19) 0.8122(2) 0.16277(5) 0.0122(3) Uani 1 1 d . . .
H2B H -0.0233 0.8514 0.1328 0.015 Uiso 1 1 calc R . .
Cl2 Cl 0.44913(6) -0.15397(5) 0.353595(14) 0.02000(8) Uani 1 1 d . . .
S2 S 0.35042(5) 0.11963(5) 0.328865(13) 0.01303(7) Uani 1 1 d . . .
H2 H 0.482(3) 0.144(3) 0.2698(9) 0.016 Uiso 1 1 d . . .
O3 O 0.26050(16) 1.07710(18) 0.14424(4) 0.0196(3) Uani 1 1 d . . .
C3 C 0.1235(2) 0.5179(2) 0.14434(6) 0.0180(3) Uani 1 1 d . . .
O4 O 0.32175(18) 1.0457(2) 0.21206(5) 0.0243(3) Uani 1 1 d . . .
C4 C 0.2629(3) 0.6739(3) 0.12527(9) 0.0289(4) Uani 1 1 d . . .
H4A H 0.3576 0.6592 0.1203 0.043 Uiso 1 1 calc R . .
H4B H 0.2938 0.7652 0.1453 0.043 Uiso 1 1 calc R . .
H4C H 0.2275 0.6981 0.0980 0.043 Uiso 1 1 calc R . .
C5 C 0.1532(3) 0.4899(3) 0.19088(7) 0.0291(4) Uani 1 1 d . . .
H5A H 0.2467 0.4713 0.1923 0.044 Uiso 1 1 calc R . .
H5B H 0.0552 0.3937 0.2022 0.044 Uiso 1 1 calc R . .
H5C H 0.1769 0.5867 0.2080 0.044 Uiso 1 1 calc R . .
O5 O 0.19405(17) -0.01405(16) 0.31027(5) 0.0181(2) Uani 1 1 d . . .
C6 C 0.0893(3) 0.3691(3) 0.11679(8) 0.0265(4) Uani 1 1 d . . .
H6A H 0.1868 0.3568 0.1164 0.040 Uiso 1 1 calc R . .
H6B H 0.0628 0.3853 0.0874 0.040 Uiso 1 1 calc R . .
H6C H -0.0035 0.2701 0.1289 0.040 Uiso 1 1 calc R . .
O6 O 0.7351(2) 0.18375(17) 0.23401(4) 0.0229(3) Uani 1 1 d . . .
H6 H 0.7662 0.2694 0.2194 0.034 Uiso 1 1 calc R . .
C7 C 0.0415(2) 0.9571(2) 0.19353(5) 0.0150(3) Uani 1 1 d . . .
H7A H 0.0129 1.0446 0.1882 0.018 Uiso 1 1 calc R . .
O7 O 0.88658(19) 0.45269(16) 0.32475(4) 0.0211(3) Uani 1 1 d . . .
C8 C 0.2231(2) 1.0284(2) 0.18482(6) 0.0156(3) Uani 1 1 d . . .
O8 O 0.8661(2) 0.50138(18) 0.25533(5) 0.0256(3) Uani 1 1 d . . .
C9 C 0.4360(2) 1.1652(3) 0.13387(6) 0.0215(4) Uani 1 1 d . . .
H9A H 0.4837 1.0933 0.1383 0.026 Uiso 1 1 calc R . .
H9B H 0.4953 1.2634 0.1523 0.026 Uiso 1 1 calc R . .
C10 C 0.4490(3) 1.2143(3) 0.08745(6) 0.0237(4) Uani 1 1 d . . .
H10A H 0.5649 1.2781 0.0792 0.035 Uiso 1 1 calc R . .
H10B H 0.3970 1.2811 0.0833 0.035 Uiso 1 1 calc R . .
H10C H 0.3937 1.1157 0.0695 0.035 Uiso 1 1 calc R . .
C11 C -0.2763(2) 0.9017(2) 0.16245(7) 0.0210(3) Uani 1 1 d . . .
H11A H -0.2431 0.9623 0.1896 0.032 Uiso 1 1 calc R . .
H11B H -0.3930 0.8616 0.1573 0.032 Uiso 1 1 calc R . .
H11C H -0.2115 0.9744 0.1389 0.032 Uiso 1 1 calc R . .
C12 C -0.3385(2) 0.6421(2) 0.20188(7) 0.0202(3) Uani 1 1 d . . .
H12A H -0.2915 0.6983 0.2291 0.030 Uiso 1 1 calc R . .
H12B H -0.3285 0.5435 0.1999 0.030 Uiso 1 1 calc R . .
H12C H -0.4546 0.6108 0.2005 0.030 Uiso 1 1 calc R . .
C13 C 0.5745(2) -0.0633(2) 0.30519(6) 0.0151(3) Uani 1 1 d . . .
C14 C 0.6293(2) 0.12261(19) 0.30660(5) 0.0128(3) Uani 1 1 d . . .
H14A H 0.6641 0.1612 0.3367 0.015 Uiso 1 1 calc R . .
C15 C 0.3339(2) 0.3052(2) 0.32355(6) 0.0174(3) Uani 1 1 d . . .
C16 C 0.2950(3) 0.3295(3) 0.27755(7) 0.0287(4) Uani 1 1 d . . .
H16A H 0.2838 0.4274 0.2760 0.043 Uiso 1 1 calc R . .
H16B H 0.1921 0.2333 0.2685 0.043 Uiso 1 1 calc R . .
H16C H 0.3841 0.3433 0.2585 0.043 Uiso 1 1 calc R . .
C17 C 0.4946(3) 0.4487(2) 0.33959(8) 0.0277(4) Uani 1 1 d . . .
H17A H 0.4829 0.5460 0.3426 0.042 Uiso 1 1 calc R . .
H17B H 0.5823 0.4714 0.3190 0.042 Uiso 1 1 calc R . .
H17C H 0.5223 0.4211 0.3676 0.042 Uiso 1 1 calc R . .
C18 C 0.1923(3) 0.2745(3) 0.35361(8) 0.0276(4) Uani 1 1 d . . .
H18A H 0.1788 0.3712 0.3538 0.041 Uiso 1 1 calc R . .
H18B H 0.2168 0.2536 0.3828 0.041 Uiso 1 1 calc R . .
H18C H 0.0908 0.1791 0.3435 0.041 Uiso 1 1 calc R . .
C19 C 0.7779(2) 0.2260(2) 0.27718(6) 0.0157(3) Uani 1 1 d . . .
H19A H 0.8659 0.2002 0.2846 0.019 Uiso 1 1 calc R . .
C20 C 0.8462(2) 0.4090(2) 0.28414(6) 0.0159(3) Uani 1 1 d . . .
C21 C 0.9707(3) 0.6310(2) 0.33253(7) 0.0245(4) Uani 1 1 d . . .
H21A H 0.9033 0.6770 0.3216 0.029 Uiso 1 1 calc R . .
H21B H 1.0778 0.6860 0.3175 0.029 Uiso 1 1 calc R . .
C22 C 0.9960(4) 0.6583(3) 0.38017(8) 0.0361(6) Uani 1 1 d . . .
H22A H 1.0577 0.7763 0.3861 0.054 Uiso 1 1 calc R . .
H22B H 1.0576 0.6069 0.3909 0.054 Uiso 1 1 calc R . .
H22C H 0.8892 0.6094 0.3946 0.054 Uiso 1 1 calc R . .
C23 C 0.4663(3) -0.1550(2) 0.26728(7) 0.0217(4) Uani 1 1 d . . .
H23A H 0.5249 -0.1052 0.2405 0.032 Uiso 1 1 calc R . .
H23B H 0.3654 -0.1490 0.2684 0.032 Uiso 1 1 calc R . .
H23C H 0.4387 -0.2701 0.2684 0.032 Uiso 1 1 calc R . .
C24 C 0.7209(3) -0.0902(3) 0.30947(8) 0.0250(4) Uani 1 1 d . . .
H24A H 0.7867 -0.0538 0.2831 0.038 Uiso 1 1 calc R . .
H24B H 0.6816 -0.2071 0.3141 0.038 Uiso 1 1 calc R . .
H24C H 0.7886 -0.0270 0.3340 0.038 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
Cl1 C1 1.8369(17) . ?
S1 O1 1.4921(14) . ?
S1 N1 1.6634(15) . ?
S1 C3 1.8418(18) . ?
N1 C2 1.468(2) . ?
N1 H1 0.81(3) . ?
C1 C12 1.518(3) . ?
C1 C11 1.528(3) . ?
C1 C2 1.550(2) . ?
O2 C7 1.409(2) . ?
O2 H2A 0.8400 . ?
N2 C14 1.464(2) . ?
N2 S2 1.6655(16) . ?
N2 H2 0.81(3) . ?
C2 C7 1.547(2) . ?
C2 H2B 1.0000 . ?
Cl2 C13 1.8390(17) . ?
S2 O5 1.4937(14) . ?
S2 C15 1.8362(19) . ?
O3 C8 1.329(2) . ?
O3 C9 1.466(2) . ?
C3 C4 1.518(3) . ?
C3 C5 1.523(3) . ?
C3 C6 1.532(3) . ?
O4 C8 1.207(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
O6 C19 1.401(2) . ?
O6 H6 0.8400 . ?
C7 C8 1.516(2) . ?
C7 H7A 1.0000 . ?
O7 C20 1.324(2) . ?
O7 C21 1.474(2) . ?
O8 C20 1.197(2) . ?
C9 C10 1.503(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 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C23 1.515(3) . ?
C13 C24 1.526(3) . ?
C13 C14 1.558(2) . ?
C14 C19 1.542(2) . ?
C14 H14A 1.0000 . ?
C15 C16 1.523(3) . ?
C15 C17 1.523(3) . ?
C15 C18 1.533(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.522(2) . ?
C19 H19A 1.0000 . ?
C21 C22 1.503(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 109.84(8) . . ?
O1 S1 C3 104.83(8) . . ?
N1 S1 C3 99.50(8) . . ?
C2 N1 S1 120.57(11) . . ?
C2 N1 H1 112(2) . . ?
S1 N1 H1 116(2) . . ?
C12 C1 C11 112.11(16) . . ?
C12 C1 C2 114.53(15) . . ?
C11 C1 C2 111.71(15) . . ?
C12 C1 Cl1 106.55(12) . . ?
C11 C1 Cl1 105.57(12) . . ?
C2 C1 Cl1 105.58(11) . . ?
C7 O2 H2A 109.5 . . ?
C14 N2 S2 119.18(11) . . ?
C14 N2 H2 109.2(19) . . ?
S2 N2 H2 117.8(19) . . ?
N1 C2 C7 105.68(13) . . ?
N1 C2 C1 116.29(14) . . ?
C7 C2 C1 112.23(14) . . ?
N1 C2 H2B 107.4 . . ?
C7 C2 H2B 107.4 . . ?
C1 C2 H2B 107.4 . . ?
O5 S2 N2 109.34(8) . . ?
O5 S2 C15 104.46(8) . . ?
N2 S2 C15 100.25(8) . . ?
C8 O3 C9 115.66(14) . . ?
C4 C3 C5 113.21(18) . . ?
C4 C3 C6 110.49(17) . . ?
C5 C3 C6 110.28(18) . . ?
C4 C3 S1 106.73(13) . . ?
C5 C3 S1 111.35(13) . . ?
C6 C3 S1 104.36(13) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
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 . . ?
C19 O6 H6 109.5 . . ?
O2 C7 C8 111.73(14) . . ?
O2 C7 C2 109.57(14) . . ?
C8 C7 C2 110.53(14) . . ?
O2 C7 H7A 108.3 . . ?
C8 C7 H7A 108.3 . . ?
C2 C7 H7A 108.3 . . ?
C20 O7 C21 114.69(15) . . ?
O4 C8 O3 124.57(17) . . ?
O4 C8 C7 123.73(16) . . ?
O3 C8 C7 111.60(15) . . ?
O3 C9 C10 106.30(16) . . ?
O3 C9 H9A 110.5 . . ?
C10 C9 H9A 110.5 . . ?
O3 C9 H9B 110.5 . . ?
C10 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
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 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C23 C13 C24 112.28(16) . . ?
C23 C13 C14 114.35(15) . . ?
C24 C13 C14 111.39(15) . . ?
C23 C13 Cl2 106.32(12) . . ?
C24 C13 Cl2 105.94(13) . . ?
C14 C13 Cl2 105.84(11) . . ?
N2 C14 C19 106.32(13) . . ?
N2 C14 C13 115.82(14) . . ?
C19 C14 C13 112.22(14) . . ?
N2 C14 H14A 107.4 . . ?
C19 C14 H14A 107.4 . . ?
C13 C14 H14A 107.4 . . ?
C16 C15 C17 112.44(18) . . ?
C16 C15 C18 110.52(18) . . ?
C17 C15 C18 110.58(17) . . ?
C16 C15 S2 111.61(14) . . ?
C17 C15 S2 107.16(14) . . ?
C18 C15 S2 104.18(13) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
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 . . ?
O6 C19 C20 110.87(14) . . ?
O6 C19 C14 110.42(14) . . ?
C20 C19 C14 111.47(14) . . ?
O6 C19 H19A 108.0 . . ?
C20 C19 H19A 108.0 . . ?
C14 C19 H19A 108.0 . . ?
O8 C20 O7 124.94(17) . . ?
O8 C20 C19 122.64(16) . . ?
O7 C20 C19 112.36(15) . . ?
O7 C21 C22 107.77(17) . . ?
O7 C21 H21A 110.2 . . ?
C22 C21 H21A 110.2 . . ?
O7 C21 H21B 110.2 . . ?
C22 C21 H21B 110.2 . . ?
H21A C21 H21B 108.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13 C23 H23A 109.5 . . ?
C13 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C13 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C13 C24 H24A 109.5 . . ?
C13 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C13 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O1 S1 N1 C2 -108.89(13) . . . . ?
C3 S1 N1 C2 141.46(13) . . . . ?
S1 N1 C2 C7 -164.28(11) . . . . ?
S1 N1 C2 C1 70.49(17) . . . . ?
C12 C1 C2 N1 40.1(2) . . . . ?
C11 C1 C2 N1 168.89(14) . . . . ?
Cl1 C1 C2 N1 -76.84(15) . . . . ?
C12 C1 C2 C7 -81.78(18) . . . . ?
C11 C1 C2 C7 47.1(2) . . . . ?
Cl1 C1 C2 C7 161.32(12) . . . . ?
C14 N2 S2 O5 -111.08(13) . . . . ?
C14 N2 S2 C15 139.50(13) . . . . ?
O1 S1 C3 C4 179.28(14) . . . . ?
N1 S1 C3 C4 -67.12(15) . . . . ?
O1 S1 C3 C5 -56.70(17) . . . . ?
N1 S1 C3 C5 56.90(16) . . . . ?
O1 S1 C3 C6 62.27(15) . . . . ?
N1 S1 C3 C6 175.87(13) . . . . ?
N1 C2 C7 O2 -60.83(17) . . . . ?
C1 C2 C7 O2 66.88(18) . . . . ?
N1 C2 C7 C8 62.73(17) . . . . ?
C1 C2 C7 C8 -169.57(14) . . . . ?
C9 O3 C8 O4 -3.4(3) . . . . ?
C9 O3 C8 C7 173.18(16) . . . . ?
O2 C7 C8 O4 -3.9(3) . . . . ?
C2 C7 C8 O4 -126.21(19) . . . . ?
O2 C7 C8 O3 179.51(15) . . . . ?
C2 C7 C8 O3 57.2(2) . . . . ?
C8 O3 C9 C10 -177.48(17) . . . . ?
S2 N2 C14 C19 -162.06(11) . . . . ?
S2 N2 C14 C13 72.54(17) . . . . ?
C23 C13 C14 N2 40.5(2) . . . . ?
C24 C13 C14 N2 169.11(15) . . . . ?
Cl2 C13 C14 N2 -76.19(15) . . . . ?
C23 C13 C14 C19 -81.84(19) . . . . ?
C24 C13 C14 C19 46.8(2) . . . . ?
Cl2 C13 C14 C19 161.48(12) . . . . ?
O5 S2 C15 C16 -53.22(16) . . . . ?
N2 S2 C15 C16 60.00(16) . . . . ?
O5 S2 C15 C17 -176.72(14) . . . . ?
N2 S2 C15 C17 -63.50(15) . . . . ?
O5 S2 C15 C18 66.06(15) . . . . ?
N2 S2 C15 C18 179.28(13) . . . . ?
N2 C14 C19 O6 -62.41(17) . . . . ?
C13 C14 C19 O6 65.17(19) . . . . ?
N2 C14 C19 C20 61.30(18) . . . . ?
C13 C14 C19 C20 -171.13(14) . . . . ?
C21 O7 C20 O8 -3.8(3) . . . . ?
C21 O7 C20 C19 173.38(16) . . . . ?
O6 C19 C20 O8 -3.3(3) . . . . ?
C14 C19 C20 O8 -126.7(2) . . . . ?
O6 C19 C20 O7 179.48(16) . . . . ?
C14 C19 C20 O7 56.0(2) . . . . ?
C20 O7 C21 C22 175.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        31.48
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.075
_database_code_depnum_ccdc_archive 'CCDC 977962'
