# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1846586'
_audit_update_record             
;
2018-05-31 deposited with the CCDC.
2018-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 N2 O4 S'
_chemical_formula_weight         316.33

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.2011(3)
_cell_length_b                   11.2011(3)
_cell_length_c                   9.5878(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1041.77(6)
_cell_formula_units_Z            3
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    3378
_cell_measurement_theta_min      3.6290
_cell_measurement_theta_max      27.4330

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.254
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93875
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Empirical absorption correction'

_exptl_special_details           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8942
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.638
_diffrn_reflns_theta_max         29.873
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             3404
_reflns_number_gt                2953
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_max     0.777
_reflns_Friedel_fraction_full    0.930

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0887P)²+0.1726P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1184 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3404
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   0.821
_refine_ls_restrained_S_all      0.821
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.51334(8) 0.74107(8) 0.32471(9) 0.0239(2) Uani 1 1 d . . . . .
O1 O 0.4214(3) 0.5973(3) 0.3147(3) 0.0421(8) Uani 1 1 d . . . . .
O2 O 0.6008(3) 0.8111(3) 0.2096(2) 0.0265(5) Uani 1 1 d . . . . .
O3 O 0.6075(3) 0.7589(3) 0.4543(3) 0.0332(6) Uani 1 1 d . . . . .
O4 O 0.3530(4) 0.8694(3) 0.6238(4) 0.0476(9) Uani 1 1 d . . . . .
N1 N 0.4325(3) 0.8205(3) 0.3669(4) 0.0278(7) Uani 1 1 d . . . . .
N2 N 0.4019(4) 1.3200(3) 0.3504(3) 0.0315(7) Uani 1 1 d . . . . .
C1 C 0.5275(4) 0.9705(3) 0.3954(3) 0.0220(6) Uani 1 1 d . . . . .
C2 C 0.6430(4) 0.9914(4) 0.4944(4) 0.0262(7) Uani 1 1 d . . . . .
C3 C 0.7226(4) 1.1164(5) 0.5625(5) 0.0365(9) Uani 1 1 d . . . . .
C4 C 0.8320(5) 1.1395(6) 0.6473(5) 0.0498(13) Uani 1 1 d . . . . .
C5 C 0.8625(6) 1.0360(7) 0.6687(5) 0.0533(14) Uani 1 1 d . . . . .
C6 C 0.7860(5) 0.9098(6) 0.6042(4) 0.0427(11) Uani 1 1 d . . . . .
C7 C 0.6790(4) 0.8910(4) 0.5167(4) 0.0288(7) Uani 1 1 d . . . . .
C8 C 0.4440(4) 1.0349(4) 0.4460(4) 0.0241(7) Uani 1 1 d . . . . .
C9 C 0.4542(4) 1.1518(3) 0.3808(3) 0.0229(7) Uani 1 1 d . . . . .
C10 C 0.5379(4) 1.2403(4) 0.2704(4) 0.0268(7) Uani 1 1 d . . . . .
C11 C 0.5029(5) 1.3412(4) 0.2563(4) 0.0350(9) Uani 1 1 d . . . . .
C12 C 0.3700(4) 1.2053(4) 0.4283(4) 0.0256(7) Uani 1 1 d . . . . .
C13 C 0.2766(4) 1.1438(4) 0.5385(4) 0.0311(8) Uani 1 1 d . . . . .
C14 C 0.2713(4) 1.0325(4) 0.6028(4) 0.0330(9) Uani 1 1 d . . . . .
C15 C 0.3550(4) 0.9799(4) 0.5587(4) 0.0298(8) Uani 1 1 d . . . . .
H1 H 0.563(5) 1.008(5) 0.306(5) 0.028(11) Uiso 1 1 d . . . . .
H1N H 0.380(5) 0.781(5) 0.439(5) 0.033(12) Uiso 1 1 d . . . . .
H2N H 0.376(5) 1.376(5) 0.368(5) 0.037(13) Uiso 1 1 d . . . . .
H14 H 0.213(5) 0.988(5) 0.687(5) 0.044(13) Uiso 1 1 d . . . . .
H10 H 0.599(5) 1.224(5) 0.216(5) 0.035(12) Uiso 1 1 d . . . . .
H6 H 0.794(6) 0.824(6) 0.627(6) 0.057(16) Uiso 1 1 d . . . . .
H11 H 0.531(6) 1.422(6) 0.194(6) 0.053(15) Uiso 1 1 d . . . . .
H4 H 0.892(6) 1.228(6) 0.693(6) 0.053(15) Uiso 1 1 d . . . . .
H13 H 0.226(5) 1.181(5) 0.568(5) 0.037(12) Uiso 1 1 d . . . . .
H3 H 0.702(5) 1.185(5) 0.550(5) 0.039(12) Uiso 1 1 d . . . . .
H5 H 0.927(6) 1.047(6) 0.722(6) 0.046(14) Uiso 1 1 d . . . . .
H1O H 0.284(9) 0.830(9) 0.683(8) 0.09(3) Uiso 1 1 d . . . . .


_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
S O2 1.423(3) . ?
S O1 1.416(3) . ?
S O3 1.577(3) . ?
S N1 1.606(3) . ?
O3 C7 1.416(5) . ?
O4 C15 1.376(5) . ?
N1 C1 1.497(4) . ?
N2 C12 1.370(5) . ?
N2 C11 1.371(6) . ?
C1 C8 1.518(5) . ?
C1 C2 1.526(5) . ?
C2 C7 1.388(5) . ?
C2 C3 1.391(6) . ?
C3 C4 1.383(7) . ?
C4 C5 1.378(8) . ?
C5 C6 1.380(8) . ?
C6 C7 1.391(6) . ?
C8 C15 1.388(5) . ?
C8 C9 1.402(5) . ?
C9 C12 1.422(5) . ?
C9 C10 1.433(5) . ?
C10 C11 1.375(5) . ?
C12 C13 1.402(6) . ?
C13 C14 1.366(6) . ?
C14 C15 1.399(5) . ?

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 S O1 118.90(17) . . ?
O2 S O3 107.99(16) . . ?
O1 S O3 104.92(18) . . ?
O2 S N1 108.25(16) . . ?
O1 S N1 110.87(17) . . ?
O3 S N1 104.96(16) . . ?
C7 O3 S 117.3(2) . . ?
C1 N1 S 112.8(2) . . ?
C12 N2 C11 109.1(3) . . ?
N1 C1 C8 109.3(3) . . ?
N1 C1 C2 111.0(3) . . ?
C8 C1 C2 113.9(3) . . ?
C7 C2 C3 116.4(4) . . ?
C7 C2 C1 122.6(3) . . ?
C3 C2 C1 120.9(3) . . ?
C4 C3 C2 121.7(5) . . ?
C5 C4 C3 120.0(5) . . ?
C4 C5 C6 120.5(4) . . ?
C5 C6 C7 118.2(5) . . ?
C2 C7 C6 123.2(4) . . ?
C2 C7 O3 122.7(3) . . ?
C6 C7 O3 114.0(3) . . ?
C15 C8 C9 117.8(3) . . ?
C15 C8 C1 120.9(3) . . ?
C9 C8 C1 121.3(3) . . ?
C8 C9 C12 119.3(3) . . ?
C8 C9 C10 134.0(3) . . ?
C12 C9 C10 106.6(3) . . ?
C11 C10 C9 106.6(3) . . ?
N2 C11 C10 110.0(3) . . ?
N2 C12 C13 130.7(3) . . ?
N2 C12 C9 107.7(3) . . ?
C13 C12 C9 121.6(3) . . ?
C14 C13 C12 118.0(3) . . ?
C13 C14 C15 121.0(4) . . ?
O4 C15 C8 116.0(3) . . ?
O4 C15 C14 121.9(3) . . ?
C8 C15 C14 122.2(3) . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.050

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1875758'
_audit_update_record             
;
2018-10-28 deposited with the CCDC.
2018-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 Cl2 N3 O4 S'
_chemical_formula_weight         400.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+5/6'
'y, -x+y, z+1/6'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'

_cell_length_a                   23.7500(5)
_cell_length_b                   23.7500(5)
_cell_length_c                   5.12390(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2502.99(12)
_cell_formula_units_Z            6
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9862
_cell_measurement_theta_min      3.722
_cell_measurement_theta_max      72.45

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    4.924
_shelx_estimated_absorpt_T_min   0.757
_shelx_estimated_absorpt_T_max   0.827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Empirical absorption correction'

_exptl_special_details           
;
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker S8 x-ray diffraction'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52942
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.148
_diffrn_reflns_theta_max         72.445
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3256
_reflns_number_gt                3061
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.962
_reflns_Friedel_fraction_full    0.979

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3, Bruker'
_computing_cell_refinement       'APEX3, Bruker'
_computing_data_reduction        'APEX3, Bruker'
_computing_structure_solution    SHELXS-2014
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1160P)²+2.2525P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1266 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.045(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3256
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1669
_refine_ls_wR_factor_gt          0.1632
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.003
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.07327(7) 0.23042(8) 1.1022(3) 0.0416(4) Uani 1 1 d . . . . .
Cl2 Cl 0.04920(9) 0.17568(9) 0.3421(5) 0.0568(6) Uani 1 1 d . . . . .
S S 0.04392(6) 0.43461(7) 0.8826(3) 0.0257(3) Uani 1 1 d . . . . .
O1 O 0.0047(2) 0.4272(2) 0.6627(10) 0.0361(11) Uani 1 1 d . . . . .
O2 O 0.0454(2) 0.4712(2) 1.1032(10) 0.0358(10) Uani 1 1 d . . . . .
O3 O 0.20500(19) 0.5080(2) 0.2167(9) 0.0291(9) Uani 1 1 d . . . . .
N1 N 0.1162(2) 0.4566(2) 0.7883(11) 0.0252(10) Uani 1 1 d . . . . .
N2 N 0.0197(2) 0.3625(2) 0.9948(9) 0.0189(9) Uani 1 1 d . . . . .
H2 H 0.0021 0.3502 1.1505 0.023 Uiso 1 1 calc R U . . .
N3 N 0.3858(2) 0.4914(3) 0.4532(12) 0.0311(12) Uani 1 1 d . . . . .
C1 C 0.1215(3) 0.4155(3) 0.5828(12) 0.0242(11) Uani 1 1 d . . . . .
C2 C 0.0770(3) 0.3435(3) 0.6401(13) 0.0278(12) Uani 1 1 d . . . . .
C3 C 0.0285(3) 0.3212(3) 0.8300(13) 0.0292(12) Uani 1 1 d . . . . .
C4 C -0.0136(3) 0.2545(3) 0.8690(16) 0.0322(13) Uani 1 1 d . . . . .
C5 C -0.0070(3) 0.2097(3) 0.7212(17) 0.0385(15) Uani 1 1 d . . . . .
H5 H -0.0349 0.1644 0.7482 0.046 Uiso 1 1 calc R U . . .
C6 C 0.0412(3) 0.2321(3) 0.5318(17) 0.0383(16) Uani 1 1 d . . . . .
C7 C 0.0825(3) 0.2971(3) 0.4903(16) 0.0358(14) Uani 1 1 d . . . . .
H7 H 0.1150 0.3108 0.3592 0.043 Uiso 1 1 calc R U . . .
C8 C 0.1923(3) 0.4343(3) 0.5578(13) 0.0245(11) Uani 1 1 d . . . . .
C9 C 0.2201(3) 0.4084(3) 0.7278(13) 0.0279(12) Uani 1 1 d . . . . .
H9 H 0.1933 0.3783 0.8572 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2846(3) 0.4249(3) 0.7155(13) 0.0295(12) Uani 1 1 d . . . . .
H10 H 0.3025 0.4071 0.8336 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3225(3) 0.4689(3) 0.5217(13) 0.0252(11) Uani 1 1 d . . . . .
C12 C 0.2979(3) 0.4977(2) 0.3501(12) 0.0235(11) Uani 1 1 d . . . . .
C13 C 0.2317(3) 0.4804(3) 0.3740(12) 0.0238(11) Uani 1 1 d . . . . .
C14 C 0.4013(3) 0.5324(3) 0.2445(14) 0.0311(13) Uani 1 1 d . . . . .
H14 H 0.4422 0.5533 0.1589 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3490(3) 0.5390(3) 0.1769(13) 0.0277(12) Uani 1 1 d . . . . .
H15 H 0.3472 0.5656 0.0423 0.033 Uiso 1 1 calc R U . . .
O4 O 0.2735(2) 0.6179(2) -0.0961(11) 0.0390(10) Uiso 1 1 d . . . . .
H1A H 0.109(3) 0.425(3) 0.418(14) 0.014(13) Uiso 1 1 d . . . . .
H1 H 0.141(3) 0.464(3) 0.910(14) 0.013(14) Uiso 1 1 d . . . . .
H3 H 0.229(3) 0.542(4) 0.121(15) 0.027(17) Uiso 1 1 d . . . . .
H3A H 0.408(4) 0.484(4) 0.52(2) 0.04(3) Uiso 1 1 d . . . . .


_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 C4 1.719(7) . ?
Cl2 C6 1.741(7) . ?
S O2 1.416(5) . ?
S O1 1.416(5) . ?
S N1 1.598(5) . ?
S N2 1.616(4) . ?
O3 C13 1.377(7) . ?
O3 H3 0.87(8) . ?
N1 C1 1.484(8) . ?
N1 H1 0.82(7) . ?
N2 C3 1.386(8) . ?
N2 H2 0.8800 . ?
N3 C11 1.366(7) . ?
N3 C14 1.367(9) . ?
N3 H3A 0.74(9) . ?
C1 C8 1.514(7) . ?
C1 C2 1.523(8) . ?
C1 H1A 0.96(7) . ?
C2 C3 1.394(8) . ?
C2 C7 1.401(9) . ?
C3 C4 1.402(8) . ?
C4 C5 1.376(10) . ?
C5 C6 1.387(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.371(9) . ?
C7 H7 0.9500 . ?
C8 C13 1.391(8) . ?
C8 C9 1.406(8) . ?
C9 C10 1.380(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.395(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.409(8) . ?
C12 C13 1.418(7) . ?
C12 C15 1.426(8) . ?
C14 C15 1.370(9) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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 S O1 121.6(3) . . ?
O2 S N1 110.4(3) . . ?
O1 S N1 109.4(3) . . ?
O2 S N2 104.7(3) . . ?
O1 S N2 106.8(3) . . ?
N1 S N2 102.0(2) . . ?
C13 O3 H3 121(5) . . ?
C1 N1 S 115.6(4) . . ?
C1 N1 H1 112(4) . . ?
S N1 H1 113(5) . . ?
C3 N2 S 115.7(4) . . ?
C3 N2 H2 122.2 . . ?
S N2 H2 122.2 . . ?
C11 N3 C14 109.4(5) . . ?
C11 N3 H3A 124(8) . . ?
C14 N3 H3A 126(8) . . ?
N1 C1 C8 108.3(5) . . ?
N1 C1 C2 111.2(5) . . ?
C8 C1 C2 113.1(5) . . ?
N1 C1 H1A 110(4) . . ?
C8 C1 H1A 107(4) . . ?
C2 C1 H1A 108(4) . . ?
C3 C2 C7 117.9(6) . . ?
C3 C2 C1 122.6(5) . . ?
C7 C2 C1 119.4(5) . . ?
N2 C3 C2 123.0(5) . . ?
N2 C3 C4 116.0(6) . . ?
C2 C3 C4 121.0(6) . . ?
C5 C4 C3 120.2(6) . . ?
C5 C4 Cl1 121.3(5) . . ?
C3 C4 Cl1 118.5(5) . . ?
C4 C5 C6 118.6(6) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C7 C6 C5 121.9(6) . . ?
C7 C6 Cl2 119.2(6) . . ?
C5 C6 Cl2 118.8(5) . . ?
C6 C7 C2 120.4(6) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
C13 C8 C9 119.1(5) . . ?
C13 C8 C1 119.9(5) . . ?
C9 C8 C1 120.9(5) . . ?
C10 C9 C8 123.0(6) . . ?
C10 C9 H9 118.5 . . ?
C8 C9 H9 118.5 . . ?
C9 C10 C11 117.0(5) . . ?
C9 C10 H10 121.5 . . ?
C11 C10 H10 121.5 . . ?
N3 C11 C10 130.4(5) . . ?
N3 C11 C12 107.0(5) . . ?
C10 C11 C12 122.6(5) . . ?
C11 C12 C13 118.3(5) . . ?
C11 C12 C15 107.7(5) . . ?
C13 C12 C15 133.9(5) . . ?
O3 C13 C8 118.9(5) . . ?
O3 C13 C12 121.2(5) . . ?
C8 C13 C12 119.9(5) . . ?
C15 C14 N3 110.0(5) . . ?
C15 C14 H14 125.0 . . ?
N3 C14 H14 125.0 . . ?
C14 C15 C12 105.9(5) . . ?
C14 C15 H15 127.1 . . ?
C12 C15 H15 127.1 . . ?

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
O2 S N1 C1 171.5(4) . . . . ?
O1 S N1 C1 -52.2(5) . . . . ?
N2 S N1 C1 60.7(5) . . . . ?
O2 S N2 C3 -165.6(4) . . . . ?
O1 S N2 C3 64.2(5) . . . . ?
N1 S N2 C3 -50.5(5) . . . . ?
S N1 C1 C8 -168.4(4) . . . . ?
S N1 C1 C2 -43.5(6) . . . . ?
N1 C1 C2 C3 12.4(8) . . . . ?
C8 C1 C2 C3 134.6(6) . . . . ?
N1 C1 C2 C7 -170.3(5) . . . . ?
C8 C1 C2 C7 -48.2(8) . . . . ?
S N2 C3 C2 26.7(7) . . . . ?
S N2 C3 C4 -154.9(5) . . . . ?
C7 C2 C3 N2 178.0(6) . . . . ?
C1 C2 C3 N2 -4.7(9) . . . . ?
C7 C2 C3 C4 -0.2(9) . . . . ?
C1 C2 C3 C4 177.0(6) . . . . ?
N2 C3 C4 C5 -177.6(6) . . . . ?
C2 C3 C4 C5 0.7(10) . . . . ?
N2 C3 C4 Cl1 2.9(8) . . . . ?
C2 C3 C4 Cl1 -178.7(5) . . . . ?
C3 C4 C5 C6 -0.9(10) . . . . ?
Cl1 C4 C5 C6 178.5(6) . . . . ?
C4 C5 C6 C7 0.6(11) . . . . ?
C4 C5 C6 Cl2 -179.4(5) . . . . ?
C5 C6 C7 C2 -0.1(11) . . . . ?
Cl2 C6 C7 C2 179.9(5) . . . . ?
C3 C2 C7 C6 -0.1(10) . . . . ?
C1 C2 C7 C6 -177.4(6) . . . . ?
N1 C1 C8 C13 -93.5(6) . . . . ?
C2 C1 C8 C13 142.7(6) . . . . ?
N1 C1 C8 C9 82.9(7) . . . . ?
C2 C1 C8 C9 -40.8(8) . . . . ?
C13 C8 C9 C10 -2.4(10) . . . . ?
C1 C8 C9 C10 -178.9(6) . . . . ?
C8 C9 C10 C11 -0.6(10) . . . . ?
C14 N3 C11 C10 177.9(6) . . . . ?
C14 N3 C11 C12 -0.7(7) . . . . ?
C9 C10 C11 N3 -176.1(6) . . . . ?
C9 C10 C11 C12 2.3(9) . . . . ?
N3 C11 C12 C13 177.7(5) . . . . ?
C10 C11 C12 C13 -1.0(8) . . . . ?
N3 C11 C12 C15 -0.5(6) . . . . ?
C10 C11 C12 C15 -179.3(6) . . . . ?
C9 C8 C13 O3 -176.8(5) . . . . ?
C1 C8 C13 O3 -0.3(8) . . . . ?
C9 C8 C13 C12 3.7(9) . . . . ?
C1 C8 C13 C12 -179.8(5) . . . . ?
C11 C12 C13 O3 178.4(5) . . . . ?
C15 C12 C13 O3 -3.9(10) . . . . ?
C11 C12 C13 C8 -2.1(8) . . . . ?
C15 C12 C13 C8 175.6(6) . . . . ?
C11 N3 C14 C15 1.7(7) . . . . ?
N3 C14 C15 C12 -1.9(7) . . . . ?
C11 C12 C15 C14 1.5(7) . . . . ?
C13 C12 C15 C14 -176.4(6) . . . . ?

_refine_diff_density_max         1.290
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.124

_shelxl_version_number           2014-1

