# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 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.
#
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#  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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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_140719e

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 N3 O4 S2'
_chemical_formula_weight         453.52

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                   10.0474(9)
_cell_length_b                   16.5840(14)
_cell_length_c                   13.7955(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.968(2)
_cell_angle_gamma                90.00
_cell_volume                     2210.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1084
_cell_measurement_theta_min      2.443
_cell_measurement_theta_max      19.149

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9197
_exptl_absorpt_correction_T_max  0.9652
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10990
_diffrn_reflns_av_R_equivalents  0.1187
_diffrn_reflns_av_sigmaI/netI    0.1642
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3895
_reflns_number_gt                1456
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of 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)+(0.0004P)²+0.0000P] 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         3895
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1663
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0877
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_restrained_S_all      0.894
_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
N1 N 0.2149(3) -0.02501(19) 0.0823(3) 0.0504(10) Uani 1 1 d . . .
H1 H 0.2595 -0.0457 0.0434 0.060 Uiso 1 1 calc R . .
N2 N 0.3571(4) 0.0942(2) 0.1325(3) 0.0512(10) Uani 1 1 d . . .
N3 N 0.4316(4) 0.0688(2) 0.0786(3) 0.0622(12) Uani 1 1 d . . .
O1 O 0.3016(3) 0.16284(16) 0.3143(2) 0.0739(10) Uani 1 1 d . . .
O2 O 0.0796(3) 0.11556(16) 0.3393(2) 0.0721(10) Uani 1 1 d . . .
O3 O 0.5964(4) 0.12740(17) -0.0083(3) 0.1082(15) Uani 1 1 d . . .
O4 O 0.6780(3) 0.09907(17) 0.1735(3) 0.1108(15) Uani 1 1 d . . .
S1 S 0.16001(14) 0.13923(7) 0.27309(10) 0.0584(4) Uani 1 1 d . . .
S2 S 0.57370(15) 0.12980(7) 0.08874(14) 0.0748(5) Uani 1 1 d . . .
C1 C 0.2487(5) 0.0447(3) 0.1363(3) 0.0449(12) Uani 1 1 d . . .
C2 C 0.1543(4) 0.0589(2) 0.1903(3) 0.0446(12) Uani 1 1 d . . .
C3 C 0.0566(5) -0.0050(2) 0.1683(3) 0.0465(12) Uani 1 1 d . . .
C4 C 0.0980(5) -0.0564(3) 0.1006(3) 0.0457(12) Uani 1 1 d . . .
C5 C 0.0266(5) -0.1268(2) 0.0627(4) 0.0583(13) Uani 1 1 d . . .
H5 H 0.0563 -0.1606 0.0190 0.070 Uiso 1 1 calc R . .
C6 C -0.0886(5) -0.1435(3) 0.0927(4) 0.0630(14) Uani 1 1 d . . .
H6 H -0.1376 -0.1906 0.0700 0.076 Uiso 1 1 calc R . .
C7 C -0.1353(5) -0.0927(3) 0.1560(4) 0.0684(16) Uani 1 1 d . . .
H7 H -0.2171 -0.1053 0.1717 0.082 Uiso 1 1 calc R . .
C8 C -0.0646(5) -0.0244(3) 0.1961(3) 0.0546(13) Uani 1 1 d . . .
H8 H -0.0955 0.0082 0.2404 0.065 Uiso 1 1 calc R . .
C9 C 0.0731(5) 0.2189(2) 0.1968(3) 0.0477(12) Uani 1 1 d . . .
C10 C -0.0603(5) 0.2367(3) 0.1945(4) 0.0653(15) Uani 1 1 d . . .
H10 H -0.1056 0.2068 0.2328 0.078 Uiso 1 1 calc R . .
C11 C -0.1283(5) 0.3002(3) 0.1339(4) 0.0781(17) Uani 1 1 d . . .
H11 H -0.2190 0.3129 0.1324 0.094 Uiso 1 1 calc R . .
C12 C -0.0615(6) 0.3437(3) 0.0768(4) 0.0656(15) Uani 1 1 d . . .
C13 C 0.0724(5) 0.3249(3) 0.0801(4) 0.0622(14) Uani 1 1 d . . .
H13 H 0.1182 0.3543 0.0416 0.075 Uiso 1 1 calc R . .
C14 C 0.1394(5) 0.2629(3) 0.1399(4) 0.0552(13) Uani 1 1 d . . .
H14 H 0.2305 0.2506 0.1419 0.066 Uiso 1 1 calc R . .
C15 C -0.1374(5) 0.4117(3) 0.0114(4) 0.109(2) Uani 1 1 d . . .
H15A H -0.2297 0.3947 -0.0226 0.163 Uiso 1 1 calc R . .
H15B H -0.0893 0.4259 -0.0374 0.163 Uiso 1 1 calc R . .
H15C H -0.1412 0.4576 0.0529 0.163 Uiso 1 1 calc R . .
C16 C 0.5291(4) 0.2271(3) 0.1142(4) 0.0524(13) Uani 1 1 d . . .
C17 C 0.5529(5) 0.2535(3) 0.2113(4) 0.0715(16) Uani 1 1 d . . .
H17 H 0.5906 0.2185 0.2643 0.086 Uiso 1 1 calc R . .
C18 C 0.5214(5) 0.3317(4) 0.2314(4) 0.0810(18) Uani 1 1 d . . .
H18 H 0.5383 0.3491 0.2978 0.097 Uiso 1 1 calc R . .
C19 C 0.4654(5) 0.3837(3) 0.1539(5) 0.0713(16) Uani 1 1 d . . .
C20 C 0.4400(4) 0.3572(3) 0.0575(4) 0.0655(15) Uani 1 1 d . . .
H20 H 0.4003 0.3923 0.0049 0.079 Uiso 1 1 calc R . .
C21 C 0.4715(4) 0.2789(3) 0.0350(4) 0.0578(14) Uani 1 1 d . . .
H21 H 0.4544 0.2618 -0.0315 0.069 Uiso 1 1 calc R . .
C22 C 0.4289(6) 0.4694(3) 0.1768(5) 0.127(3) Uani 1 1 d . . .
H22A H 0.4612 0.5065 0.1349 0.190 Uiso 1 1 calc R . .
H22B H 0.4723 0.4814 0.2464 0.190 Uiso 1 1 calc R . .
H22C H 0.3303 0.4743 0.1635 0.190 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
N1 C1 1.366(5) . ?
N1 C4 1.370(4) . ?
N1 H1 0.8600 . ?
N2 N3 1.265(4) . ?
N2 C1 1.377(5) . ?
N3 S2 1.723(3) . ?
O1 S1 1.434(3) . ?
O2 S1 1.431(3) . ?
O3 S2 1.419(3) . ?
O4 S2 1.433(3) . ?
S1 C2 1.746(4) . ?
S1 C9 1.764(4) . ?
S2 C16 1.736(4) . ?
C1 C2 1.378(5) . ?
C2 C3 1.420(5) . ?
C3 C4 1.408(5) . ?
C3 C8 1.411(5) . ?
C4 C5 1.394(5) . ?
C5 C6 1.361(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.370(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.363(5) . ?
C9 C14 1.370(5) . ?
C10 C11 1.400(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(6) . ?
C12 C15 1.512(6) . ?
C13 C14 1.374(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.366(6) . ?
C16 C21 1.385(5) . ?
C17 C18 1.381(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.356(6) . ?
C19 C22 1.523(6) . ?
C20 C21 1.391(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
C1 N1 C4 108.5(4) . . ?
C1 N1 H1 125.7 . . ?
C4 N1 H1 125.7 . . ?
N3 N2 C1 115.2(4) . . ?
N2 N3 S2 111.6(3) . . ?
O2 S1 O1 119.7(2) . . ?
O2 S1 C2 106.6(2) . . ?
O1 S1 C2 108.6(2) . . ?
O2 S1 C9 108.2(2) . . ?
O1 S1 C9 107.9(2) . . ?
C2 S1 C9 105.0(2) . . ?
O3 S2 O4 119.3(3) . . ?
O3 S2 N3 104.6(2) . . ?
O4 S2 N3 105.12(19) . . ?
O3 S2 C16 109.5(2) . . ?
O4 S2 C16 109.7(3) . . ?
N3 S2 C16 107.93(19) . . ?
N1 C1 N2 124.4(4) . . ?
N1 C1 C2 109.5(4) . . ?
N2 C1 C2 125.9(4) . . ?
C1 C2 C3 107.2(4) . . ?
C1 C2 S1 125.5(4) . . ?
C3 C2 S1 127.3(3) . . ?
C4 C3 C8 118.5(4) . . ?
C4 C3 C2 106.3(4) . . ?
C8 C3 C2 135.2(4) . . ?
N1 C4 C5 128.8(4) . . ?
N1 C4 C3 108.5(4) . . ?
C5 C4 C3 122.7(4) . . ?
C6 C5 C4 116.7(5) . . ?
C6 C5 H5 121.7 . . ?
C4 C5 H5 121.7 . . ?
C5 C6 C7 122.1(5) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C8 C7 C6 122.0(5) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C3 117.9(5) . . ?
C7 C8 H8 121.0 . . ?
C3 C8 H8 121.0 . . ?
C10 C9 C14 120.1(4) . . ?
C10 C9 S1 119.8(4) . . ?
C14 C9 S1 120.1(4) . . ?
C9 C10 C11 119.4(5) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 120.2(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 119.5(5) . . ?
C13 C12 C15 121.2(5) . . ?
C11 C12 C15 119.3(5) . . ?
C12 C13 C14 120.3(5) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 120.4(4) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
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 . . ?
C17 C16 C21 119.8(4) . . ?
C17 C16 S2 120.7(5) . . ?
C21 C16 S2 119.4(4) . . ?
C16 C17 C18 120.7(5) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 120.1(5) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 119.3(5) . . ?
C20 C19 C22 121.0(6) . . ?
C18 C19 C22 119.7(6) . . ?
C19 C20 C21 121.9(5) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C16 C21 C20 118.3(4) . . ?
C16 C21 H21 120.9 . . ?
C20 C21 H21 120.9 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N3 S2 -174.0(3) . . . . ?
N2 N3 S2 O3 -146.1(3) . . . . ?
N2 N3 S2 O4 87.5(4) . . . . ?
N2 N3 S2 C16 -29.5(4) . . . . ?
C4 N1 C1 N2 -176.9(4) . . . . ?
C4 N1 C1 C2 0.2(5) . . . . ?
N3 N2 C1 N1 -3.9(6) . . . . ?
N3 N2 C1 C2 179.5(4) . . . . ?
N1 C1 C2 C3 -0.3(5) . . . . ?
N2 C1 C2 C3 176.8(4) . . . . ?
N1 C1 C2 S1 177.7(3) . . . . ?
N2 C1 C2 S1 -5.2(7) . . . . ?
O2 S1 C2 C1 -158.5(4) . . . . ?
O1 S1 C2 C1 -28.3(5) . . . . ?
C9 S1 C2 C1 86.8(4) . . . . ?
O2 S1 C2 C3 19.1(4) . . . . ?
O1 S1 C2 C3 149.3(4) . . . . ?
C9 S1 C2 C3 -95.6(4) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
S1 C2 C3 C4 -177.7(3) . . . . ?
C1 C2 C3 C8 -177.9(5) . . . . ?
S1 C2 C3 C8 4.2(7) . . . . ?
C1 N1 C4 C5 -179.5(4) . . . . ?
C1 N1 C4 C3 0.0(5) . . . . ?
C8 C3 C4 N1 178.4(4) . . . . ?
C2 C3 C4 N1 -0.1(5) . . . . ?
C8 C3 C4 C5 -2.1(6) . . . . ?
C2 C3 C4 C5 179.4(4) . . . . ?
N1 C4 C5 C6 -179.3(4) . . . . ?
C3 C4 C5 C6 1.2(6) . . . . ?
C4 C5 C6 C7 1.4(7) . . . . ?
C5 C6 C7 C8 -3.2(7) . . . . ?
C6 C7 C8 C3 2.2(7) . . . . ?
C4 C3 C8 C7 0.3(6) . . . . ?
C2 C3 C8 C7 178.3(5) . . . . ?
O2 S1 C9 C10 -12.2(4) . . . . ?
O1 S1 C9 C10 -143.0(4) . . . . ?
C2 S1 C9 C10 101.4(4) . . . . ?
O2 S1 C9 C14 167.8(3) . . . . ?
O1 S1 C9 C14 37.0(4) . . . . ?
C2 S1 C9 C14 -78.6(4) . . . . ?
C14 C9 C10 C11 -0.2(7) . . . . ?
S1 C9 C10 C11 179.8(4) . . . . ?
C9 C10 C11 C12 0.5(8) . . . . ?
C10 C11 C12 C13 -0.5(8) . . . . ?
C10 C11 C12 C15 179.6(5) . . . . ?
C11 C12 C13 C14 0.1(7) . . . . ?
C15 C12 C13 C14 -180.0(5) . . . . ?
C10 C9 C14 C13 -0.2(7) . . . . ?
S1 C9 C14 C13 179.8(3) . . . . ?
C12 C13 C14 C9 0.2(7) . . . . ?
O3 S2 C16 C17 -154.8(4) . . . . ?
O4 S2 C16 C17 -22.1(4) . . . . ?
N3 S2 C16 C17 91.9(4) . . . . ?
O3 S2 C16 C21 23.9(4) . . . . ?
O4 S2 C16 C21 156.6(3) . . . . ?
N3 S2 C16 C21 -89.4(4) . . . . ?
C21 C16 C17 C18 -0.7(7) . . . . ?
S2 C16 C17 C18 177.9(4) . . . . ?
C16 C17 C18 C19 0.2(8) . . . . ?
C17 C18 C19 C20 0.7(8) . . . . ?
C17 C18 C19 C22 179.1(4) . . . . ?
C18 C19 C20 C21 -1.1(8) . . . . ?
C22 C19 C20 C21 -179.5(4) . . . . ?
C17 C16 C21 C20 0.3(6) . . . . ?
S2 C16 C21 C20 -178.4(3) . . . . ?
C19 C20 C21 C16 0.7(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 1021404'
#######################################################################
#
#                 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_140818e

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N3 O2 S'
_chemical_formula_weight         299.34

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1000(8)
_cell_length_b                   9.2299(11)
_cell_length_c                   12.3601(13)
_cell_angle_alpha                94.1800(10)
_cell_angle_beta                 104.161(2)
_cell_angle_gamma                111.952(3)
_cell_volume                     716.16(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    434
_cell_measurement_theta_min      2.709
_cell_measurement_theta_max      23.021

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9124
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3425
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_av_sigmaI/netI    0.2848
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2433
_reflns_number_gt                835
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of 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)+(0.1269P)²+0.0000P] 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         2433
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2827
_refine_ls_R_factor_gt           0.1337
_refine_ls_wR_factor_ref         0.3498
_refine_ls_wR_factor_gt          0.3089
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.3765(6) 0.9616(4) 0.2438(3) 0.0554(11) Uani 1 1 d . . .
N1 N 0.2927(13) 0.6491(10) 0.4978(7) 0.038(2) Uani 1 1 d . . .
H1 H 0.3199 0.7425 0.5319 0.046 Uiso 1 1 calc R . .
N2 N 0.3105(14) 0.7032(10) 0.3097(7) 0.043(2) Uani 1 1 d . . .
N3 N 0.3559(15) 0.8496(10) 0.3470(7) 0.050(3) Uani 1 1 d . . .
O1 O 0.5622(16) 1.1053(9) 0.2982(7) 0.087(3) Uani 1 1 d . . .
O2 O 0.1763(15) 0.9674(10) 0.2053(8) 0.079(3) Uani 1 1 d . . .
C1 C 0.2818(17) 0.6101(13) 0.3877(9) 0.039(3) Uani 1 1 d . . .
C2 C 0.2313(16) 0.4447(12) 0.3632(9) 0.039(3) Uani 1 1 d . . .
C3 C 0.2083(16) 0.3902(12) 0.4626(9) 0.039(3) Uani 1 1 d . . .
C4 C 0.2544(16) 0.5193(12) 0.5446(10) 0.040(3) Uani 1 1 d . . .
C5 C 0.2449(17) 0.5008(14) 0.6563(9) 0.045(3) Uani 1 1 d . . .
H5 H 0.2683 0.5861 0.7103 0.054 Uiso 1 1 calc R . .
C6 C 0.2001(17) 0.3531(14) 0.6805(10) 0.054(3) Uani 1 1 d . . .
H6 H 0.1961 0.3386 0.7537 0.065 Uiso 1 1 calc R . .
C7 C 0.1603(17) 0.2236(13) 0.6025(11) 0.054(3) Uani 1 1 d . . .
H7 H 0.1284 0.1249 0.6242 0.065 Uiso 1 1 calc R . .
C8 C 0.1662(17) 0.2361(12) 0.4933(10) 0.047(3) Uani 1 1 d . . .
H8 H 0.1441 0.1489 0.4414 0.056 Uiso 1 1 calc R . .
C9 C 0.194(2) 0.3524(14) 0.2504(10) 0.063(4) Uani 1 1 d . . .
H9A H 0.2565 0.2767 0.2602 0.095 Uiso 1 1 calc R . .
H9B H 0.2563 0.4235 0.2039 0.095 Uiso 1 1 calc R . .
H9C H 0.0435 0.2974 0.2144 0.095 Uiso 1 1 calc R . .
C10 C 0.424(2) 0.8638(15) 0.1357(10) 0.057(4) Uani 1 1 d . . .
C11 C 0.252(2) 0.7415(15) 0.0517(11) 0.067(4) Uani 1 1 d . . .
H11 H 0.1118 0.7154 0.0519 0.080 Uiso 1 1 calc R . .
C12 C 0.298(3) 0.6649(17) -0.0282(11) 0.076(4) Uani 1 1 d . . .
H12 H 0.1872 0.5823 -0.0821 0.091 Uiso 1 1 calc R . .
C13 C 0.499(3) 0.7027(18) -0.0337(11) 0.072(4) Uani 1 1 d . . .
H13 H 0.5226 0.6438 -0.0892 0.087 Uiso 1 1 calc R . .
C14 C 0.668(2) 0.8267(18) 0.0418(13) 0.076(4) Uani 1 1 d . . .
H14 H 0.8051 0.8555 0.0363 0.091 Uiso 1 1 calc R . .
C15 C 0.627(3) 0.9085(16) 0.1271(11) 0.067(4) Uani 1 1 d . . .
H15 H 0.7385 0.9938 0.1786 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 1.407(9) . ?
S1 O1 1.442(8) . ?
S1 N3 1.698(9) . ?
S1 C10 1.728(13) . ?
N1 C4 1.334(12) . ?
N1 C1 1.358(12) . ?
N1 H1 0.8600 . ?
N2 N3 1.286(10) . ?
N2 C1 1.341(13) . ?
C1 C2 1.422(13) . ?
C2 C3 1.384(14) . ?
C2 C9 1.488(13) . ?
C3 C4 1.387(13) . ?
C3 C8 1.439(14) . ?
C4 C5 1.418(14) . ?
C5 C6 1.353(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(15) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(15) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.378(16) . ?
C10 C11 1.423(16) . ?
C11 C12 1.348(17) . ?
C11 H11 0.9300 . ?
C12 C13 1.356(17) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(17) . ?
C13 H13 0.9300 . ?
C14 C15 1.401(17) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

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 120.0(6) . . ?
O2 S1 N3 104.9(5) . . ?
O1 S1 N3 103.8(5) . . ?
O2 S1 C10 110.0(6) . . ?
O1 S1 C10 109.3(7) . . ?
N3 S1 C10 108.0(5) . . ?
C4 N1 C1 109.0(9) . . ?
C4 N1 H1 125.5 . . ?
C1 N1 H1 125.5 . . ?
N3 N2 C1 113.8(9) . . ?
N2 N3 S1 112.4(7) . . ?
N2 C1 N1 129.2(10) . . ?
N2 C1 C2 122.3(10) . . ?
N1 C1 C2 108.6(10) . . ?
C3 C2 C1 105.1(9) . . ?
C3 C2 C9 128.9(10) . . ?
C1 C2 C9 125.8(10) . . ?
C2 C3 C4 108.2(10) . . ?
C2 C3 C8 132.0(10) . . ?
C4 C3 C8 119.6(10) . . ?
N1 C4 C3 109.0(10) . . ?
N1 C4 C5 129.5(10) . . ?
C3 C4 C5 121.3(10) . . ?
C6 C5 C4 116.9(10) . . ?
C6 C5 H5 121.6 . . ?
C4 C5 H5 121.6 . . ?
C5 C6 C7 123.3(12) . . ?
C5 C6 H6 118.3 . . ?
C7 C6 H6 118.3 . . ?
C6 C7 C8 121.7(11) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C3 117.1(10) . . ?
C7 C8 H8 121.5 . . ?
C3 C8 H8 121.5 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 119.5(12) . . ?
C15 C10 S1 120.4(11) . . ?
C11 C10 S1 120.0(12) . . ?
C12 C11 C10 117.6(14) . . ?
C12 C11 H11 121.2 . . ?
C10 C11 H11 121.2 . . ?
C11 C12 C13 123.0(14) . . ?
C11 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C12 C13 C14 120.9(14) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 117.9(14) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C10 C15 C14 120.8(13) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?

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
C1 N2 N3 S1 -176.6(8) . . . . ?
O2 S1 N3 N2 96.1(8) . . . . ?
O1 S1 N3 N2 -137.1(8) . . . . ?
C10 S1 N3 N2 -21.2(10) . . . . ?
N3 N2 C1 N1 0.5(16) . . . . ?
N3 N2 C1 C2 -179.8(9) . . . . ?
C4 N1 C1 N2 -179.6(11) . . . . ?
C4 N1 C1 C2 0.6(11) . . . . ?
N2 C1 C2 C3 -178.3(10) . . . . ?
N1 C1 C2 C3 1.5(11) . . . . ?
N2 C1 C2 C9 -3.1(17) . . . . ?
N1 C1 C2 C9 176.6(9) . . . . ?
C1 C2 C3 C4 -3.0(11) . . . . ?
C9 C2 C3 C4 -177.9(10) . . . . ?
C1 C2 C3 C8 -177.1(11) . . . . ?
C9 C2 C3 C8 8.0(19) . . . . ?
C1 N1 C4 C3 -2.6(12) . . . . ?
C1 N1 C4 C5 -178.8(10) . . . . ?
C2 C3 C4 N1 3.6(12) . . . . ?
C8 C3 C4 N1 178.5(9) . . . . ?
C2 C3 C4 C5 -179.9(10) . . . . ?
C8 C3 C4 C5 -5.0(15) . . . . ?
N1 C4 C5 C6 179.2(10) . . . . ?
C3 C4 C5 C6 3.5(15) . . . . ?
C4 C5 C6 C7 -1.4(17) . . . . ?
C5 C6 C7 C8 0.9(18) . . . . ?
C6 C7 C8 C3 -2.3(16) . . . . ?
C2 C3 C8 C7 177.8(11) . . . . ?
C4 C3 C8 C7 4.3(15) . . . . ?
O2 S1 C10 C15 146.2(9) . . . . ?
O1 S1 C10 C15 12.6(11) . . . . ?
N3 S1 C10 C15 -99.8(10) . . . . ?
O2 S1 C10 C11 -30.7(11) . . . . ?
O1 S1 C10 C11 -164.3(9) . . . . ?
N3 S1 C10 C11 83.3(10) . . . . ?
C15 C10 C11 C12 5.5(17) . . . . ?
S1 C10 C11 C12 -177.5(10) . . . . ?
C10 C11 C12 C13 -2(2) . . . . ?
C11 C12 C13 C14 -2(2) . . . . ?
C12 C13 C14 C15 3(2) . . . . ?
C11 C10 C15 C14 -5.0(18) . . . . ?
S1 C10 C15 C14 178.1(10) . . . . ?
C13 C14 C15 C10 0.9(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.102
_database_code_depnum_ccdc_archive 'CCDC 1021405'
