# 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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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_131021_zhw_1021

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H14 Cl N O4 S'
_chemical_formula_sum            'C19 H14 Cl N O4 S'
_chemical_formula_weight         387.82

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'
Cl Cl 0.1484 0.1585 '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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   6.4358(3)
_cell_length_b                   12.1826(7)
_cell_length_c                   12.7387(7)
_cell_angle_alpha                103.653(5)
_cell_angle_beta                 103.478(5)
_cell_angle_gamma                95.006(4)
_cell_volume                     933.06(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2079
_cell_measurement_theta_min      3.2807
_cell_measurement_theta_max      29.4621

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8620
_exptl_absorpt_correction_T_max  0.8873
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent Technologies, 2011) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5913
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3410
_reflns_number_gt                2606
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0476P)²+0.1945P] 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         3410
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 -0.28007(9) -0.43196(6) 0.59677(6) 0.0626(2) Uani 1 1 d . . .
S1 S 0.30206(9) 0.13590(6) 0.55935(5) 0.0512(2) Uani 1 1 d . . .
O1 O 0.1248(3) 0.08566(17) 0.46409(14) 0.0701(6) Uani 1 1 d . . .
O2 O 0.5087(3) 0.16460(17) 0.54303(15) 0.0646(5) Uani 1 1 d . . .
O3 O 0.6159(2) 0.13345(15) 0.76876(14) 0.0589(5) Uani 1 1 d . . .
O4 O 0.8431(2) -0.10763(15) 1.00998(13) 0.0546(4) Uani 1 1 d . . .
N1 N 0.3138(3) 0.04226(17) 0.63429(15) 0.0471(5) Uani 1 1 d . . .
H1 H 0.2144 -0.0164 0.6116 0.057 Uiso 1 1 calc R . .
C1 C 0.0396(4) 0.2477(3) 0.6712(2) 0.0623(7) Uani 1 1 d . . .
H1A H -0.0534 0.1787 0.6467 0.075 Uiso 1 1 calc R . .
C2 C -0.0138(5) 0.3419(3) 0.7357(3) 0.0786(10) Uani 1 1 d . . .
H2 H -0.1429 0.3368 0.7563 0.094 Uiso 1 1 calc R . .
C3 C 0.1228(6) 0.4444(3) 0.7703(3) 0.0901(10) Uani 1 1 d . . .
H3 H 0.0852 0.5084 0.8139 0.108 Uiso 1 1 calc R . .
C4 C 0.3148(6) 0.4526(3) 0.7405(3) 0.0869(10) Uani 1 1 d . . .
H4 H 0.4060 0.5222 0.7636 0.104 Uiso 1 1 calc R . .
C5 C 0.3717(4) 0.3587(2) 0.6771(3) 0.0659(8) Uani 1 1 d . . .
H5 H 0.5018 0.3638 0.6574 0.079 Uiso 1 1 calc R . .
C6 C 0.2341(3) 0.2567(2) 0.6428(2) 0.0495(6) Uani 1 1 d . . .
C7 C 0.4733(3) 0.0519(2) 0.73133(18) 0.0414(5) Uani 1 1 d . . .
C8 C 0.4552(3) -0.04431(18) 0.78389(17) 0.0360(5) Uani 1 1 d . . .
C9 C 0.6141(3) -0.04086(19) 0.87395(17) 0.0380(5) Uani 1 1 d . . .
H9 H 0.7196 0.0235 0.8988 0.046 Uiso 1 1 calc R . .
C10 C 0.6418(3) -0.12424(19) 0.93691(17) 0.0399(5) Uani 1 1 d . . .
C11 C 0.5262(4) -0.2173(2) 0.9456(2) 0.0591(7) Uani 1 1 d . . .
H11 H 0.3847 -0.2480 0.9053 0.071 Uiso 1 1 calc R . .
C12 C 0.6576(5) -0.2601(3) 1.0265(2) 0.0734(8) Uani 1 1 d . . .
H12 H 0.6195 -0.3237 1.0504 0.088 Uiso 1 1 calc R . .
C13 C 0.8474(4) -0.1920(3) 1.0625(2) 0.0680(8) Uani 1 1 d . . .
H13 H 0.9658 -0.2011 1.1159 0.082 Uiso 1 1 calc R . .
C14 C 0.2702(3) -0.13999(17) 0.73510(16) 0.0333(5) Uani 1 1 d . . .
C15 C 0.0942(3) -0.1419(2) 0.78035(19) 0.0467(6) Uani 1 1 d . . .
H15 H 0.0889 -0.0818 0.8397 0.056 Uiso 1 1 calc R . .
C16 C -0.0731(3) -0.2321(2) 0.73819(19) 0.0489(6) Uani 1 1 d . . .
H16 H -0.1902 -0.2332 0.7693 0.059 Uiso 1 1 calc R . .
C17 C -0.0656(3) -0.31981(19) 0.65048(19) 0.0401(5) Uani 1 1 d . . .
C18 C 0.1052(4) -0.3204(2) 0.60342(19) 0.0462(5) Uani 1 1 d . . .
H18 H 0.1082 -0.3806 0.5435 0.055 Uiso 1 1 calc R . .
C19 C 0.2732(3) -0.22998(19) 0.64653(18) 0.0411(5) Uani 1 1 d . . .
H19 H 0.3902 -0.2298 0.6153 0.049 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 C17 1.740(2) . ?
S1 O2 1.4198(16) . ?
S1 O1 1.4250(17) . ?
S1 N1 1.6474(18) . ?
S1 C6 1.755(3) . ?
O3 C7 1.212(3) . ?
O4 C13 1.351(3) . ?
O4 C10 1.374(2) . ?
N1 C7 1.384(3) . ?
N1 H1 0.8600 . ?
C1 C2 1.365(4) . ?
C1 C6 1.384(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.376(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.490(3) . ?
C8 C9 1.337(3) . ?
C8 C14 1.494(3) . ?
C9 C10 1.434(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.342(3) . ?
C11 C12 1.405(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.332(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.380(3) . ?
C14 C15 1.387(3) . ?
C15 C16 1.378(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(3) . ?
C18 C19 1.384(3) . ?
C18 H18 0.9300 . ?
C19 H19 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 119.03(11) . . ?
O2 S1 N1 109.85(10) . . ?
O1 S1 N1 104.04(10) . . ?
O2 S1 C6 109.01(11) . . ?
O1 S1 C6 109.51(11) . . ?
N1 S1 C6 104.35(10) . . ?
C13 O4 C10 107.30(19) . . ?
C7 N1 S1 124.19(15) . . ?
C7 N1 H1 117.9 . . ?
S1 N1 H1 117.9 . . ?
C2 C1 C6 119.0(3) . . ?
C2 C1 H1A 120.5 . . ?
C6 C1 H1A 120.5 . . ?
C1 C2 C3 120.3(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 121.1(3) . . ?
C5 C6 S1 119.9(2) . . ?
C1 C6 S1 119.0(2) . . ?
O3 C7 N1 121.2(2) . . ?
O3 C7 C8 123.75(19) . . ?
N1 C7 C8 115.06(18) . . ?
C9 C8 C7 116.45(18) . . ?
C9 C8 C14 122.82(19) . . ?
C7 C8 C14 120.71(17) . . ?
C8 C9 C10 127.9(2) . . ?
C8 C9 H9 116.0 . . ?
C10 C9 H9 116.0 . . ?
C11 C10 O4 108.22(19) . . ?
C11 C10 C9 138.2(2) . . ?
O4 C10 C9 113.56(18) . . ?
C10 C11 C12 107.7(2) . . ?
C10 C11 H11 126.2 . . ?
C12 C11 H11 126.2 . . ?
C13 C12 C11 106.7(2) . . ?
C13 C12 H12 126.7 . . ?
C11 C12 H12 126.7 . . ?
C12 C13 O4 110.1(2) . . ?
C12 C13 H13 124.9 . . ?
O4 C13 H13 124.9 . . ?
C19 C14 C15 118.47(19) . . ?
C19 C14 C8 121.02(18) . . ?
C15 C14 C8 120.49(19) . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 121.4(2) . . ?
C16 C17 Cl1 118.96(16) . . ?
C18 C17 Cl1 119.65(18) . . ?
C17 C18 C19 118.8(2) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C14 C19 C18 121.13(19) . . ?
C14 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 979066'
