  
data_shelx 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C18 H18 Cl2 N2 O4 S' 
_chemical_formula_weight          429.30 
  
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            Triclinic 
_symmetry_space_group_name_H-M    P-1 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
  
_cell_length_a                    8.6136(12) 
_cell_length_b                    11.2490(15) 
_cell_length_c                    11.7697(17) 
_cell_angle_alpha                 113.5820(10) 
_cell_angle_beta                  108.764(2) 
_cell_angle_gamma                 96.299(2) 
_cell_volume                      951.5(2) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     113(2) 
_cell_measurement_reflns_used           3602 
_cell_measurement_theta_min             3.2 
_cell_measurement_theta_max             27.5 
  
_exptl_crystal_description        Prism 
_exptl_crystal_colour             Colorless 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.18 
_exptl_crystal_size_min           0.12 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.498 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              444 
_exptl_absorpt_coefficient_mu     0.478 
_exptl_absorpt_correction_type    MULTI-SCAN 
_exptl_absorpt_correction_T_min   0.9104 
_exptl_absorpt_correction_T_max   0.9448 
_exptl_absorpt_process_details    'REQAB (Rigaku, 1998)' 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       113(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'rotating anode' 
_diffrn_radiation_monochromator   multilayer 
_diffrn_measurement_device_type   'Rigaku XtaLAB P200' 
_diffrn_measurement_method        'ω and φ scans' 
_diffrn_detector_area_resol_mean  5.814 
_diffrn_standards_number          0 
_diffrn_standards_interval_count  0 
_diffrn_standards_interval_time   0 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             12342 
_diffrn_reflns_av_R_equivalents   0.0274 
_diffrn_reflns_av_sigmaI/netI     0.0223 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          3.15 
_diffrn_reflns_theta_max          27.53 
_reflns_number_total              4308 
_reflns_number_gt                 3984 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection   'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)' 
_computing_cell_refinement    'CrystalClear-SM Expert 2.1 b42' 
_computing_data_reduction     'CrystalClear-SM Expert 2.1 b42' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'CrystalStructure 4.1' 
_computing_publication_material   'CrystalStructure 4.1 (Rigaku, 2014)' 
  
_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)+(0.0432P)²+0.4269P] 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          4308 
_refine_ls_number_parameters      246 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0312 
_refine_ls_R_factor_gt            0.0294 
_refine_ls_wR_factor_ref          0.0835 
_refine_ls_wR_factor_gt           0.0825 
_refine_ls_goodness_of_fit_ref    1.077 
_refine_ls_restrained_S_all       1.077 
_refine_ls_shift/su_max           0.002 
_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 -0.00534(4) 0.13086(3) 0.95406(3) 0.01938(9) Uani 1 1 d . . . 
Cl1 Cl -0.00836(5) 0.51612(3) 1.17347(3) 0.02557(10) Uani 1 1 d . . . 
Cl2 Cl 0.34962(4) 0.50306(3) 1.12137(4) 0.02741(10) Uani 1 1 d . . . 
O1 O 0.33421(13) 0.06115(11) 1.13016(10) 0.0249(2) Uani 1 1 d . . . 
O2 O 0.79533(19) 0.45007(14) 1.49658(11) 0.0499(4) Uani 1 1 d . . . 
O3 O 0.53510(12) 0.15430(11) 0.58880(9) 0.0211(2) Uani 1 1 d . . . 
O4 O 0.26136(13) 0.17886(11) 0.44138(10) 0.0239(2) Uani 1 1 d . . . 
N1 N -0.08024(15) 0.25370(12) 1.03340(12) 0.0206(2) Uani 1 1 d . . . 
N2 N 0.58187(15) 0.22792(12) 1.24690(11) 0.0191(2) Uani 1 1 d . . . 
C1 C 0.03349(17) 0.36834(14) 1.08519(13) 0.0187(3) Uani 1 1 d . . . 
C2 C 0.18611(16) 0.36382(13) 1.06306(12) 0.0172(2) Uani 1 1 d . . . 
C3 C 0.18303(16) 0.23359(13) 0.98780(12) 0.0159(2) Uani 1 1 d . . . 
C4 C 0.31128(16) 0.18485(12) 0.93476(12) 0.0151(2) Uani 1 1 d . . . 
C5 C 0.43484(17) 0.14866(13) 1.00575(12) 0.0167(2) Uani 1 1 d . . . 
H5 H 0.5209 0.1253 0.9739 0.020 Uiso 1 1 calc R . . 
C6 C 0.44444(16) 0.14315(13) 1.13319(13) 0.0164(2) Uani 1 1 d . . . 
C7 C 0.71652(18) 0.32575(15) 1.25445(14) 0.0249(3) Uani 1 1 d . . . 
H7A H 0.6791 0.3347 1.1701 0.030 Uiso 1 1 calc R . . 
H7B H 0.8204 0.2939 1.2638 0.030 Uiso 1 1 calc R . . 
C8 C 0.7561(3) 0.46087(18) 1.37411(16) 0.0402(4) Uani 1 1 d . . . 
H8A H 0.8542 0.5242 1.3834 0.048 Uiso 1 1 calc R . . 
H8B H 0.6567 0.4980 1.3583 0.048 Uiso 1 1 calc R . . 
C9 C 0.6529(2) 0.36220(16) 1.48613(15) 0.0335(4) Uani 1 1 d . . . 
H9A H 0.5527 0.3982 1.4688 0.040 Uiso 1 1 calc R . . 
H9B H 0.6791 0.3588 1.5729 0.040 Uiso 1 1 calc R . . 
C10 C 0.61056(18) 0.22182(14) 1.37371(13) 0.0218(3) Uani 1 1 d . . . 
H10A H 0.7057 0.1815 1.3950 0.026 Uiso 1 1 calc R . . 
H10B H 0.5069 0.1644 1.3644 0.026 Uiso 1 1 calc R . . 
C11 C 0.29537(16) 0.18413(12) 0.80499(12) 0.0146(2) Uani 1 1 d . . . 
C12 C 0.14744(17) 0.19746(14) 0.72389(13) 0.0187(3) Uani 1 1 d . . . 
H12 H 0.0565 0.2083 0.7527 0.022 Uiso 1 1 calc R . . 
C13 C 0.12977(17) 0.19518(14) 0.60055(13) 0.0201(3) Uani 1 1 d . . . 
H13 H 0.0272 0.2037 0.5463 0.024 Uiso 1 1 calc R . . 
C14 C 0.26120(17) 0.18050(13) 0.55762(12) 0.0177(2) Uani 1 1 d . . . 
C15 C 0.41302(16) 0.16699(13) 0.63952(12) 0.0160(2) Uani 1 1 d . . . 
C16 C 0.42923(16) 0.16866(13) 0.76084(12) 0.0157(2) Uani 1 1 d . . . 
H16 H 0.5313 0.1593 0.8149 0.019 Uiso 1 1 calc R . . 
C17 C 0.10989(19) 0.18787(16) 0.35227(14) 0.0258(3) Uani 1 1 d . . . 
H17A H 0.0127 0.1152 0.3280 0.039 Uiso 1 1 calc R . . 
H17B H 0.1237 0.1793 0.2701 0.039 Uiso 1 1 calc R . . 
H17C H 0.0895 0.2753 0.3976 0.039 Uiso 1 1 calc R . . 
C18 C 0.68870(16) 0.13637(15) 0.66591(14) 0.0208(3) Uani 1 1 d . . . 
H18A H 0.7470 0.2170 0.7538 0.031 Uiso 1 1 calc R . . 
H18B H 0.7634 0.1220 0.6169 0.031 Uiso 1 1 calc R . . 
H18C H 0.6609 0.0578 0.6798 0.031 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 N1 1.6578(12) . ? 
S1 C3 1.7125(13) . ? 
Cl1 C1 1.7214(13) . ? 
Cl2 C2 1.7153(14) . ? 
O1 C6 1.2303(17) . ? 
O2 C9 1.427(2) . ? 
O2 C8 1.4291(19) . ? 
O3 C15 1.3606(15) . ? 
O3 C18 1.4308(15) . ? 
O4 C14 1.3613(15) . ? 
O4 C17 1.4304(16) . ? 
N1 C1 1.3054(19) . ? 
N2 C6 1.3467(17) . ? 
N2 C7 1.4628(17) . ? 
N2 C10 1.4634(16) . ? 
C1 C2 1.4222(18) . ? 
C2 C3 1.3673(18) . ? 
C3 C4 1.4878(17) . ? 
C4 C5 1.3386(18) . ? 
C4 C11 1.4855(16) . ? 
C5 C6 1.5020(16) . ? 
C5 H5 0.9500 . ? 
C7 C8 1.508(2) . ? 
C7 H7A 0.9900 . ? 
C7 H7B 0.9900 . ? 
C8 H8A 0.9900 . ? 
C8 H8B 0.9900 . ? 
C9 C10 1.506(2) . ? 
C9 H9A 0.9900 . ? 
C9 H9B 0.9900 . ? 
C10 H10A 0.9900 . ? 
C10 H10B 0.9900 . ? 
C11 C12 1.3896(17) . ? 
C11 C16 1.4096(17) . ? 
C12 C13 1.3994(18) . ? 
C12 H12 0.9500 . ? 
C13 C14 1.3808(18) . ? 
C13 H13 0.9500 . ? 
C14 C15 1.4186(17) . ? 
C15 C16 1.3815(17) . ? 
C16 H16 0.9500 . ? 
C17 H17A 0.9800 . ? 
C17 H17B 0.9800 . ? 
C17 H17C 0.9800 . ? 
C18 H18A 0.9800 . ? 
C18 H18B 0.9800 . ? 
C18 H18C 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 
N1 S1 C3 96.06(6) . . ? 
C9 O2 C8 109.91(13) . . ? 
C15 O3 C18 116.64(10) . . ? 
C14 O4 C17 117.61(11) . . ? 
C1 N1 S1 108.19(9) . . ? 
C6 N2 C7 124.67(11) . . ? 
C6 N2 C10 120.50(11) . . ? 
C7 N2 C10 114.74(11) . . ? 
N1 C1 C2 117.39(12) . . ? 
N1 C1 Cl1 119.25(10) . . ? 
C2 C1 Cl1 123.35(11) . . ? 
C3 C2 C1 110.57(12) . . ? 
C3 C2 Cl2 124.98(10) . . ? 
C1 C2 Cl2 124.45(10) . . ? 
C2 C3 C4 127.99(12) . . ? 
C2 C3 S1 107.79(9) . . ? 
C4 C3 S1 124.11(9) . . ? 
C5 C4 C11 123.94(11) . . ? 
C5 C4 C3 119.78(11) . . ? 
C11 C4 C3 116.25(11) . . ? 
C4 C5 C6 123.40(11) . . ? 
C4 C5 H5 118.3 . . ? 
C6 C5 H5 118.3 . . ? 
O1 C6 N2 122.99(12) . . ? 
O1 C6 C5 120.54(12) . . ? 
N2 C6 C5 116.41(11) . . ? 
N2 C7 C8 109.86(12) . . ? 
N2 C7 H7A 109.7 . . ? 
C8 C7 H7A 109.7 . . ? 
N2 C7 H7B 109.7 . . ? 
C8 C7 H7B 109.7 . . ? 
H7A C7 H7B 108.2 . . ? 
O2 C8 C7 111.49(14) . . ? 
O2 C8 H8A 109.3 . . ? 
C7 C8 H8A 109.3 . . ? 
O2 C8 H8B 109.3 . . ? 
C7 C8 H8B 109.3 . . ? 
H8A C8 H8B 108.0 . . ? 
O2 C9 C10 111.30(13) . . ? 
O2 C9 H9A 109.4 . . ? 
C10 C9 H9A 109.4 . . ? 
O2 C9 H9B 109.4 . . ? 
C10 C9 H9B 109.4 . . ? 
H9A C9 H9B 108.0 . . ? 
N2 C10 C9 109.33(11) . . ? 
N2 C10 H10A 109.8 . . ? 
C9 C10 H10A 109.8 . . ? 
N2 C10 H10B 109.8 . . ? 
C9 C10 H10B 109.8 . . ? 
H10A C10 H10B 108.3 . . ? 
C12 C11 C16 118.58(11) . . ? 
C12 C11 C4 120.66(11) . . ? 
C16 C11 C4 120.76(11) . . ? 
C11 C12 C13 121.29(12) . . ? 
C11 C12 H12 119.4 . . ? 
C13 C12 H12 119.4 . . ? 
C14 C13 C12 120.09(12) . . ? 
C14 C13 H13 120.0 . . ? 
C12 C13 H13 120.0 . . ? 
O4 C14 C13 125.92(12) . . ? 
O4 C14 C15 114.88(11) . . ? 
C13 C14 C15 119.20(11) . . ? 
O3 C15 C16 125.01(11) . . ? 
O3 C15 C14 114.59(11) . . ? 
C16 C15 C14 120.39(11) . . ? 
C15 C16 C11 120.45(11) . . ? 
C15 C16 H16 119.8 . . ? 
C11 C16 H16 119.8 . . ? 
O4 C17 H17A 109.5 . . ? 
O4 C17 H17B 109.5 . . ? 
H17A C17 H17B 109.5 . . ? 
O4 C17 H17C 109.5 . . ? 
H17A C17 H17C 109.5 . . ? 
H17B C17 H17C 109.5 . . ? 
O3 C18 H18A 109.5 . . ? 
O3 C18 H18B 109.5 . . ? 
H18A C18 H18B 109.5 . . ? 
O3 C18 H18C 109.5 . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 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 
C3 S1 N1 C1 -0.76(10) . . . . ? 
S1 N1 C1 C2 0.49(15) . . . . ? 
S1 N1 C1 Cl1 179.48(7) . . . . ? 
N1 C1 C2 C3 0.15(17) . . . . ? 
Cl1 C1 C2 C3 -178.79(9) . . . . ? 
N1 C1 C2 Cl2 179.44(10) . . . . ? 
Cl1 C1 C2 Cl2 0.49(17) . . . . ? 
C1 C2 C3 C4 175.76(12) . . . . ? 
Cl2 C2 C3 C4 -3.52(19) . . . . ? 
C1 C2 C3 S1 -0.69(13) . . . . ? 
Cl2 C2 C3 S1 -179.97(8) . . . . ? 
N1 S1 C3 C2 0.85(10) . . . . ? 
N1 S1 C3 C4 -175.77(11) . . . . ? 
C2 C3 C4 C5 94.31(17) . . . . ? 
S1 C3 C4 C5 -89.78(14) . . . . ? 
C2 C3 C4 C11 -83.74(16) . . . . ? 
S1 C3 C4 C11 92.17(13) . . . . ? 
C11 C4 C5 C6 -176.80(11) . . . . ? 
C3 C4 C5 C6 5.31(19) . . . . ? 
C7 N2 C6 O1 179.32(13) . . . . ? 
C10 N2 C6 O1 2.8(2) . . . . ? 
C7 N2 C6 C5 1.99(19) . . . . ? 
C10 N2 C6 C5 -174.53(11) . . . . ? 
C4 C5 C6 O1 65.55(18) . . . . ? 
C4 C5 C6 N2 -117.05(15) . . . . ? 
C6 N2 C7 C8 133.33(14) . . . . ? 
C10 N2 C7 C8 -49.97(17) . . . . ? 
C9 O2 C8 C7 -60.8(2) . . . . ? 
N2 C7 C8 O2 53.9(2) . . . . ? 
C8 O2 C9 C10 61.8(2) . . . . ? 
C6 N2 C10 C9 -132.44(14) . . . . ? 
C7 N2 C10 C9 50.71(16) . . . . ? 
O2 C9 C10 N2 -55.68(17) . . . . ? 
C5 C4 C11 C12 167.47(13) . . . . ? 
C3 C4 C11 C12 -14.57(17) . . . . ? 
C5 C4 C11 C16 -11.93(19) . . . . ? 
C3 C4 C11 C16 166.02(11) . . . . ? 
C16 C11 C12 C13 0.3(2) . . . . ? 
C4 C11 C12 C13 -179.15(12) . . . . ? 
C11 C12 C13 C14 -0.5(2) . . . . ? 
C17 O4 C14 C13 -2.6(2) . . . . ? 
C17 O4 C14 C15 178.11(12) . . . . ? 
C12 C13 C14 O4 -178.90(13) . . . . ? 
C12 C13 C14 C15 0.4(2) . . . . ? 
C18 O3 C15 C16 2.45(19) . . . . ? 
C18 O3 C15 C14 -178.21(12) . . . . ? 
O4 C14 C15 O3 -0.09(17) . . . . ? 
C13 C14 C15 O3 -179.46(12) . . . . ? 
O4 C14 C15 C16 179.29(12) . . . . ? 
C13 C14 C15 C16 -0.1(2) . . . . ? 
O3 C15 C16 C11 179.16(12) . . . . ? 
C14 C15 C16 C11 -0.15(19) . . . . ? 
C12 C11 C16 C15 0.06(19) . . . . ? 
C4 C11 C16 C15 179.47(11) . . . . ? 
  
_diffrn_measured_fraction_theta_max    0.981 
_diffrn_reflns_theta_full              27.53 
_diffrn_measured_fraction_theta_full   0.981 
_refine_diff_density_max    0.705 
_refine_diff_density_min   -0.415 
_refine_diff_density_rms    0.053 
