# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_160711b
_database_code_depnum_ccdc_archive 'CCDC 1569841'
_audit_update_record             
;
2017-08-20 deposited with the CCDC.
2017-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 Cl N2 O3 S'
_chemical_formula_weight         376.85

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   P2(1)/n

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

_cell_length_a                   13.2285(11)
_cell_length_b                   9.3407(8)
_cell_length_c                   14.9536(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.0870(10)
_cell_angle_gamma                90.00
_cell_volume                     1840.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1765
_cell_measurement_theta_min      2.574
_cell_measurement_theta_max      20.86

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8676
_exptl_absorpt_correction_T_max  0.9668
_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            8904
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_sigmaI/netI    0.1664
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3240
_reflns_number_gt                1791
_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)+(0.0001P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3240
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.2046
_refine_ls_wR_factor_gt          0.1500
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_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 0.44358(12) 0.48493(16) 0.70682(8) 0.1033(6) Uani 1 1 d . . .
N1 N 0.4685(2) 0.0361(3) 0.2488(2) 0.0548(8) Uani 1 1 d . . .
N2 N 0.4318(2) 0.1092(3) 0.32029(19) 0.0525(8) Uani 1 1 d . . .
O1 O 0.6883(2) 0.1470(5) 0.3732(2) 0.1122(14) Uani 1 1 d . . .
O2 O 0.4378(2) -0.0677(3) 0.09903(19) 0.0757(9) Uani 1 1 d . . .
O3 O 0.2941(2) -0.0280(3) 0.19074(18) 0.0739(9) Uani 1 1 d . . .
S1 S 0.38642(7) 0.01911(11) 0.15889(6) 0.0572(4) Uani 1 1 d . . .
C1 C 0.5054(3) 0.1542(4) 0.3749(2) 0.0526(10) Uani 1 1 d . . .
C2 C 0.6039(3) 0.1199(5) 0.3399(3) 0.0660(12) Uani 1 1 d . . .
C3 C 0.5801(3) 0.0489(5) 0.2495(3) 0.0570(10) Uani 1 1 d . . .
C4 C 0.4900(3) 0.2336(4) 0.4570(2) 0.0515(9) Uani 1 1 d . . .
C5 C 0.4051(3) 0.3167(5) 0.4620(3) 0.0610(11) Uani 1 1 d . . .
H5 H 0.3568 0.3208 0.4130 0.073 Uiso 1 1 calc R . .
C6 C 0.3902(3) 0.3944(5) 0.5385(3) 0.0665(12) Uani 1 1 d . . .
H6 H 0.3324 0.4505 0.5409 0.080 Uiso 1 1 calc R . .
C7 C 0.4611(4) 0.3876(5) 0.6103(3) 0.0691(12) Uani 1 1 d . . .
C8 C 0.5464(4) 0.3049(6) 0.6069(3) 0.0807(14) Uani 1 1 d . . .
H8 H 0.5943 0.3008 0.6563 0.097 Uiso 1 1 calc R . .
C9 C 0.5613(3) 0.2277(5) 0.5303(3) 0.0732(13) Uani 1 1 d . . .
H9 H 0.6193 0.1720 0.5280 0.088 Uiso 1 1 calc R . .
C10 C 0.6159(3) 0.1475(5) 0.1777(3) 0.0652(11) Uani 1 1 d . . .
H10A H 0.6038 0.1027 0.1200 0.098 Uiso 1 1 calc R . .
H10B H 0.6873 0.1656 0.1901 0.098 Uiso 1 1 calc R . .
H10C H 0.5794 0.2363 0.1778 0.098 Uiso 1 1 calc R . .
C11 C 0.6315(4) -0.0981(5) 0.2470(4) 0.0920(16) Uani 1 1 d . . .
H11A H 0.6194 -0.1510 0.3001 0.138 Uiso 1 1 calc R . .
H11B H 0.7032 -0.0856 0.2444 0.138 Uiso 1 1 calc R . .
H11C H 0.6040 -0.1498 0.1949 0.138 Uiso 1 1 calc R . .
C12 C 0.3684(2) 0.1899(4) 0.1125(2) 0.0485(9) Uani 1 1 d . . .
C13 C 0.3203(3) 0.2957(5) 0.1588(2) 0.0564(10) Uani 1 1 d . . .
H13 H 0.2958 0.2751 0.2137 0.068 Uiso 1 1 calc R . .
C14 C 0.3093(3) 0.4299(5) 0.1230(3) 0.0625(11) Uani 1 1 d . . .
H14 H 0.2780 0.5004 0.1548 0.075 Uiso 1 1 calc R . .
C15 C 0.3434(3) 0.4639(5) 0.0406(3) 0.0609(11) Uani 1 1 d . . .
C16 C 0.3908(3) 0.3555(5) -0.0037(3) 0.0642(11) Uani 1 1 d . . .
H16 H 0.4149 0.3757 -0.0589 0.077 Uiso 1 1 calc R . .
C17 C 0.4032(3) 0.2204(5) 0.0306(2) 0.0578(11) Uani 1 1 d . . .
H17 H 0.4348 0.1500 -0.0010 0.069 Uiso 1 1 calc R . .
C18 C 0.3288(4) 0.6093(5) 0.0006(3) 0.0884(15) Uani 1 1 d . . .
H18A H 0.3687 0.6183 -0.0497 0.133 Uiso 1 1 calc R . .
H18B H 0.3498 0.6803 0.0448 0.133 Uiso 1 1 calc R . .
H18C H 0.2584 0.6230 -0.0192 0.133 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 C7 1.739(4) . ?
N1 N2 1.392(4) . ?
N1 C3 1.480(4) . ?
N1 S1 1.659(3) . ?
N2 C1 1.284(4) . ?
O1 C2 1.207(5) . ?
O2 S1 1.425(3) . ?
O3 S1 1.419(3) . ?
S1 C12 1.747(4) . ?
C1 C4 1.464(5) . ?
C1 C2 1.482(5) . ?
C2 C3 1.514(6) . ?
C3 C10 1.521(5) . ?
C3 C11 1.535(6) . ?
C4 C5 1.372(5) . ?
C4 C9 1.382(5) . ?
C5 C6 1.384(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.363(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(6) . ?
C8 C9 1.383(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.376(5) . ?
C12 C13 1.392(5) . ?
C13 C14 1.366(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(6) . ?
C15 C18 1.490(6) . ?
C16 C17 1.367(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
N2 N1 C3 111.7(3) . . ?
N2 N1 S1 114.9(2) . . ?
C3 N1 S1 126.5(2) . . ?
C1 N2 N1 110.7(3) . . ?
O3 S1 O2 120.47(19) . . ?
O3 S1 N1 106.17(16) . . ?
O2 S1 N1 104.42(17) . . ?
O3 S1 C12 108.95(18) . . ?
O2 S1 C12 109.06(17) . . ?
N1 S1 C12 106.90(16) . . ?
N2 C1 C4 123.0(3) . . ?
N2 C1 C2 110.2(3) . . ?
C4 C1 C2 126.7(3) . . ?
O1 C2 C1 128.2(4) . . ?
O1 C2 C3 124.8(4) . . ?
C1 C2 C3 106.9(3) . . ?
N1 C3 C2 99.8(3) . . ?
N1 C3 C10 114.6(3) . . ?
C2 C3 C10 108.2(3) . . ?
N1 C3 C11 111.8(4) . . ?
C2 C3 C11 110.9(4) . . ?
C10 C3 C11 111.0(3) . . ?
C5 C4 C9 118.9(4) . . ?
C5 C4 C1 120.5(3) . . ?
C9 C4 C1 120.6(3) . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 119.2(4) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 120.6(4) . . ?
C6 C7 Cl1 119.8(4) . . ?
C8 C7 Cl1 119.7(4) . . ?
C7 C8 C9 120.1(4) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 119.9(4) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 119.9(4) . . ?
C17 C12 S1 119.9(3) . . ?
C13 C12 S1 120.2(3) . . ?
C14 C13 C12 119.7(4) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.7(4) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C16 117.0(4) . . ?
C14 C15 C18 121.6(4) . . ?
C16 C15 C18 121.4(4) . . ?
C17 C16 C15 122.5(4) . . ?
C17 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
C16 C17 C12 119.1(4) . . ?
C16 C17 H17 120.4 . . ?
C12 C17 H17 120.4 . . ?
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 . . ?

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 N1 N2 C1 -8.0(4) . . . . ?
S1 N1 N2 C1 -161.0(3) . . . . ?
N2 N1 S1 O3 -47.2(3) . . . . ?
C3 N1 S1 O3 164.5(3) . . . . ?
N2 N1 S1 O2 -175.5(2) . . . . ?
C3 N1 S1 O2 36.2(4) . . . . ?
N2 N1 S1 C12 69.0(3) . . . . ?
C3 N1 S1 C12 -79.3(3) . . . . ?
N1 N2 C1 C4 -179.3(3) . . . . ?
N1 N2 C1 C2 3.3(4) . . . . ?
N2 C1 C2 O1 179.4(5) . . . . ?
C4 C1 C2 O1 2.2(7) . . . . ?
N2 C1 C2 C3 2.3(5) . . . . ?
C4 C1 C2 C3 -174.9(4) . . . . ?
N2 N1 C3 C2 8.6(4) . . . . ?
S1 N1 C3 C2 157.8(3) . . . . ?
N2 N1 C3 C10 -106.7(4) . . . . ?
S1 N1 C3 C10 42.5(5) . . . . ?
N2 N1 C3 C11 125.9(4) . . . . ?
S1 N1 C3 C11 -84.9(4) . . . . ?
O1 C2 C3 N1 176.4(5) . . . . ?
C1 C2 C3 N1 -6.3(4) . . . . ?
O1 C2 C3 C10 -63.5(6) . . . . ?
C1 C2 C3 C10 113.8(3) . . . . ?
O1 C2 C3 C11 58.4(6) . . . . ?
C1 C2 C3 C11 -124.3(4) . . . . ?
N2 C1 C4 C5 -28.6(6) . . . . ?
C2 C1 C4 C5 148.3(4) . . . . ?
N2 C1 C4 C9 152.4(4) . . . . ?
C2 C1 C4 C9 -30.7(6) . . . . ?
C9 C4 C5 C6 0.2(6) . . . . ?
C1 C4 C5 C6 -178.8(4) . . . . ?
C4 C5 C6 C7 -0.2(6) . . . . ?
C5 C6 C7 C8 0.0(6) . . . . ?
C5 C6 C7 Cl1 179.8(3) . . . . ?
C6 C7 C8 C9 0.2(7) . . . . ?
Cl1 C7 C8 C9 -179.6(4) . . . . ?
C5 C4 C9 C8 0.1(6) . . . . ?
C1 C4 C9 C8 179.1(4) . . . . ?
C7 C8 C9 C4 -0.2(7) . . . . ?
O3 S1 C12 C17 -133.7(3) . . . . ?
O2 S1 C12 C17 -0.4(3) . . . . ?
N1 S1 C12 C17 111.9(3) . . . . ?
O3 S1 C12 C13 47.2(3) . . . . ?
O2 S1 C12 C13 -179.5(3) . . . . ?
N1 S1 C12 C13 -67.1(3) . . . . ?
C17 C12 C13 C14 -0.9(5) . . . . ?
S1 C12 C13 C14 178.1(3) . . . . ?
C12 C13 C14 C15 1.0(6) . . . . ?
C13 C14 C15 C16 -0.8(6) . . . . ?
C13 C14 C15 C18 178.3(4) . . . . ?
C14 C15 C16 C17 0.5(6) . . . . ?
C18 C15 C16 C17 -178.6(4) . . . . ?
C15 C16 C17 C12 -0.5(6) . . . . ?
C13 C12 C17 C16 0.6(5) . . . . ?
S1 C12 C17 C16 -178.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.047
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_161110d
_database_code_depnum_ccdc_archive 'CCDC 1569842'
_audit_update_record             
;
2017-08-20 deposited with the CCDC.
2017-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 Cl2 N2 O2 S'
_chemical_formula_weight         381.26

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   P2(1)/n

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

_cell_length_a                   11.6687(9)
_cell_length_b                   8.7574(6)
_cell_length_c                   17.8369(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.5120(10)
_cell_angle_gamma                90.00
_cell_volume                     1810.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1373
_cell_measurement_theta_min      2.298
_cell_measurement_theta_max      19.275

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8966
_exptl_absorpt_correction_T_max  0.9352
_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            8877
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_sigmaI/netI    0.0717
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3194
_reflns_number_gt                1538
_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)+(0.0254P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3194
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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 1.03241(10) 0.20181(13) -0.09705(6) 0.1171(5) Uani 1 1 d . . .
Cl2 Cl 0.26360(11) -0.02911(14) 0.10447(8) 0.1300(5) Uani 1 1 d . . .
N1 N 0.6286(2) 0.5798(3) 0.18985(13) 0.0630(7) Uani 1 1 d . . .
N2 N 0.6846(2) 0.5148(3) 0.13143(13) 0.0635(8) Uani 1 1 d . . .
O1 O 0.44403(17) 0.6815(3) 0.22308(11) 0.0815(7) Uani 1 1 d . . .
O2 O 0.48686(18) 0.6890(3) 0.08995(11) 0.0777(7) Uani 1 1 d . . .
S1 S 0.49017(7) 0.61144(12) 0.16045(5) 0.0694(3) Uani 1 1 d . . .
C1 C 0.7910(3) 0.4752(4) 0.15067(17) 0.0593(9) Uani 1 1 d . . .
C2 C 0.8471(3) 0.4914(4) 0.22797(18) 0.0738(11) Uani 1 1 d . . .
H2 H 0.9272 0.4893 0.2373 0.089 Uiso 1 1 calc R . .
C3 C 0.7840(3) 0.5090(4) 0.28444(18) 0.0674(10) Uani 1 1 d . . .
C4 C 0.6551(3) 0.5095(4) 0.26463(16) 0.0756(11) Uani 1 1 d . . .
H4A H 0.6258 0.4059 0.2639 0.091 Uiso 1 1 calc R . .
H4B H 0.6189 0.5671 0.3020 0.091 Uiso 1 1 calc R . .
C5 C 0.8514(3) 0.4068(4) 0.08966(17) 0.0596(9) Uani 1 1 d . . .
C6 C 0.8092(3) 0.4245(4) 0.01519(19) 0.0783(11) Uani 1 1 d . . .
H6 H 0.7418 0.4804 0.0032 0.094 Uiso 1 1 calc R . .
C7 C 0.8635(3) 0.3620(5) -0.04253(19) 0.0830(11) Uani 1 1 d . . .
H7 H 0.8325 0.3749 -0.0925 0.100 Uiso 1 1 calc R . .
C8 C 0.9624(3) 0.2816(4) -0.0256(2) 0.0772(11) Uani 1 1 d . . .
C9 C 1.0072(3) 0.2614(4) 0.0473(2) 0.0887(12) Uani 1 1 d . . .
H9 H 1.0741 0.2043 0.0586 0.106 Uiso 1 1 calc R . .
C10 C 0.9527(3) 0.3266(4) 0.10551(19) 0.0804(11) Uani 1 1 d . . .
H10 H 0.9851 0.3156 0.1553 0.097 Uiso 1 1 calc R . .
C11 C 0.8278(3) 0.5186(4) 0.36641(18) 0.0986(13) Uani 1 1 d . . .
H11A H 0.9105 0.5143 0.3723 0.148 Uiso 1 1 calc R . .
H11B H 0.7979 0.4345 0.3928 0.148 Uiso 1 1 calc R . .
H11C H 0.8030 0.6129 0.3867 0.148 Uiso 1 1 calc R . .
C12 C 0.4266(2) 0.4306(4) 0.14536(17) 0.0617(9) Uani 1 1 d . . .
C13 C 0.3628(3) 0.3687(5) 0.19844(18) 0.0833(11) Uani 1 1 d . . .
H13 H 0.3532 0.4222 0.2423 0.100 Uiso 1 1 calc R . .
C14 C 0.3133(3) 0.2260(5) 0.1856(2) 0.0977(13) Uani 1 1 d . . .
H14 H 0.2706 0.1830 0.2212 0.117 Uiso 1 1 calc R . .
C15 C 0.3268(3) 0.1484(5) 0.1209(2) 0.0822(11) Uani 1 1 d . . .
C16 C 0.3906(3) 0.2096(5) 0.06820(19) 0.0792(11) Uani 1 1 d . . .
H16 H 0.4001 0.1558 0.0244 0.095 Uiso 1 1 calc R . .
C17 C 0.4406(3) 0.3514(5) 0.08063(17) 0.0708(10) Uani 1 1 d . . .
H17 H 0.4840 0.3934 0.0451 0.085 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 C8 1.736(3) . ?
Cl2 C15 1.731(4) . ?
N1 N2 1.411(3) . ?
N1 C4 1.470(3) . ?
N1 S1 1.663(3) . ?
N2 C1 1.297(4) . ?
O1 S1 1.4320(19) . ?
O2 S1 1.426(2) . ?
S1 C12 1.757(3) . ?
C1 C2 1.465(4) . ?
C1 C5 1.488(4) . ?
C2 C3 1.322(4) . ?
C2 H2 0.9300 . ?
C3 C11 1.495(4) . ?
C3 C4 1.505(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.372(4) . ?
C5 C10 1.376(4) . ?
C6 C7 1.382(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.357(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.356(4) . ?
C9 C10 1.399(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.373(4) . ?
C12 C13 1.380(4) . ?
C13 C14 1.384(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(4) . ?
C16 C17 1.379(4) . ?
C16 H16 0.9300 . ?
C17 H17 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
N2 N1 C4 115.7(2) . . ?
N2 N1 S1 110.42(19) . . ?
C4 N1 S1 117.0(2) . . ?
C1 N2 N1 115.0(2) . . ?
O2 S1 O1 120.59(14) . . ?
O2 S1 N1 106.60(13) . . ?
O1 S1 N1 105.24(13) . . ?
O2 S1 C12 109.01(14) . . ?
O1 S1 C12 108.42(14) . . ?
N1 S1 C12 106.03(14) . . ?
N2 C1 C2 122.4(3) . . ?
N2 C1 C5 115.6(3) . . ?
C2 C1 C5 121.9(3) . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C11 126.4(3) . . ?
C2 C3 C4 116.7(3) . . ?
C11 C3 C4 116.8(3) . . ?
N1 C4 C3 108.5(3) . . ?
N1 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
N1 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C6 C5 C10 117.5(3) . . ?
C6 C5 C1 121.0(3) . . ?
C10 C5 C1 121.5(3) . . ?
C5 C6 C7 122.2(3) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C8 C7 C6 119.4(3) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 Cl1 119.3(3) . . ?
C7 C8 Cl1 120.3(3) . . ?
C8 C9 C10 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C10 C9 120.5(3) . . ?
C5 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 120.3(4) . . ?
C17 C12 S1 119.7(3) . . ?
C13 C12 S1 120.0(3) . . ?
C12 C13 C14 119.2(4) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.5(4) . . ?
C14 C15 Cl2 120.2(3) . . ?
C16 C15 Cl2 119.2(3) . . ?
C15 C16 C17 119.6(4) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C12 C17 C16 120.1(3) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?

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
C4 N1 N2 C1 -39.3(4) . . . . ?
S1 N1 N2 C1 -175.0(2) . . . . ?
N2 N1 S1 O2 -48.9(2) . . . . ?
C4 N1 S1 O2 176.0(2) . . . . ?
N2 N1 S1 O1 -178.08(19) . . . . ?
C4 N1 S1 O1 46.8(3) . . . . ?
N2 N1 S1 C12 67.1(2) . . . . ?
C4 N1 S1 C12 -68.0(2) . . . . ?
N1 N2 C1 C2 2.2(4) . . . . ?
N1 N2 C1 C5 -179.9(2) . . . . ?
N2 C1 C2 C3 17.8(5) . . . . ?
C5 C1 C2 C3 -160.0(3) . . . . ?
C1 C2 C3 C11 176.5(3) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
N2 N1 C4 C3 54.2(3) . . . . ?
S1 N1 C4 C3 -173.0(2) . . . . ?
C2 C3 C4 N1 -33.6(4) . . . . ?
C11 C3 C4 N1 150.2(3) . . . . ?
N2 C1 C5 C6 17.6(4) . . . . ?
C2 C1 C5 C6 -164.5(3) . . . . ?
N2 C1 C5 C10 -163.9(3) . . . . ?
C2 C1 C5 C10 14.0(5) . . . . ?
C10 C5 C6 C7 1.5(5) . . . . ?
C1 C5 C6 C7 -179.9(3) . . . . ?
C5 C6 C7 C8 -0.7(6) . . . . ?
C6 C7 C8 C9 0.6(6) . . . . ?
C6 C7 C8 Cl1 180.0(3) . . . . ?
C7 C8 C9 C10 -1.4(6) . . . . ?
Cl1 C8 C9 C10 179.2(3) . . . . ?
C6 C5 C10 C9 -2.3(5) . . . . ?
C1 C5 C10 C9 179.1(3) . . . . ?
C8 C9 C10 C5 2.3(6) . . . . ?
O2 S1 C12 C17 35.5(3) . . . . ?
O1 S1 C12 C17 168.5(2) . . . . ?
N1 S1 C12 C17 -78.9(3) . . . . ?
O2 S1 C12 C13 -144.5(3) . . . . ?
O1 S1 C12 C13 -11.5(3) . . . . ?
N1 S1 C12 C13 101.1(3) . . . . ?
C17 C12 C13 C14 0.0(5) . . . . ?
S1 C12 C13 C14 180.0(3) . . . . ?
C12 C13 C14 C15 -0.5(6) . . . . ?
C13 C14 C15 C16 0.8(6) . . . . ?
C13 C14 C15 Cl2 -179.3(3) . . . . ?
C14 C15 C16 C17 -0.5(5) . . . . ?
Cl2 C15 C16 C17 179.6(3) . . . . ?
C13 C12 C17 C16 0.2(5) . . . . ?
S1 C12 C17 C16 -179.7(3) . . . . ?
C15 C16 C17 C12 0.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.044
