# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1417521'
_audit_update_record             
;
2015-08-07 deposited with the CCDC.
2016-01-21 downloaded from the CCDC.
;
_audit_creation_date             2015-05-14
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H10 Br N O4 S'
_chemical_formula_sum            'C14 H10 Br N O4 S'
_chemical_formula_weight         368.20
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.608(2)
_cell_length_b                   9.473(3)
_cell_length_c                   9.930(3)
_cell_angle_alpha                99.760(5)
_cell_angle_beta                 96.941(4)
_cell_angle_gamma                90.080(5)
_cell_volume                     700.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    3.100
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10906
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.208
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2246
_reflns_number_total             2461
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    ?
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2461
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0492P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0900
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C17(H17), C20(H20), C21(H21)
2.c Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Br1 Br 0.43284(5) 0.67200(4) 0.62581(3) 0.02857(15) Uani 1 1 d . . . . .
S2 S 0.26245(10) 0.90753(7) -0.00994(8) 0.01322(19) Uani 1 1 d . . . . .
O3 O 0.1171(3) 0.78391(19) -0.0049(2) 0.0146(5) Uani 1 1 d . . . . .
O4 O 0.4302(3) 0.8415(2) -0.0198(2) 0.0147(5) Uani 1 1 d . . . . .
O5 O 0.1904(3) 0.9851(2) -0.1147(2) 0.0189(5) Uani 1 1 d . . . . .
O6 O 0.6912(3) 0.7932(3) 0.4456(3) 0.0284(6) Uani 1 1 d . . . . .
H6 H 0.7028 0.7451 0.5097 0.043 Uiso 1 1 calc R U . . .
C7 C 0.2557(4) 1.0151(3) 0.1539(3) 0.0171(7) Uani 1 1 d . . . . .
H7A H 0.3405 1.0968 0.1647 0.021 Uiso 1 1 calc R U . . .
H7B H 0.1357 1.0545 0.1584 0.021 Uiso 1 1 calc R U . . .
C8 C 0.1685(4) 0.6393(3) -0.0322(3) 0.0136(7) Uani 1 1 d . . . . .
C9 C 0.3796(5) 0.7775(3) 0.4802(3) 0.0200(7) Uani 1 1 d . . . . .
C10 C 0.4747(4) 0.9009(3) 0.3099(3) 0.0145(7) Uani 1 1 d . . . . .
H10 H 0.5665 0.9328 0.2646 0.017 Uiso 1 1 calc R U . . .
C11 C 0.1651(4) 0.8903(3) 0.3387(3) 0.0192(7) Uani 1 1 d . . . . .
H11 H 0.0458 0.9137 0.3126 0.023 Uiso 1 1 calc R U . . .
C12 C 0.2660(4) 0.5779(3) 0.0668(3) 0.0178(7) Uani 1 1 d . . . . .
H12 H 0.3046 0.6323 0.1549 0.021 Uiso 1 1 calc R U . . .
C13 C 0.3071(4) 0.4345(3) 0.0355(4) 0.0192(7) Uani 1 1 d . . . . .
H13 H 0.3751 0.3903 0.1029 0.023 Uiso 1 1 calc R U . . .
C14 C 0.1083(4) 0.5615(3) -0.1622(3) 0.0157(7) Uani 1 1 d . . . . .
C15 C 0.2999(4) 0.9342(3) 0.2710(3) 0.0147(7) Uani 1 1 d . . . . .
N16 N -0.0930(4) 0.6759(3) -0.3407(3) 0.0289(7) Uani 1 1 d . . . . .
C17 C 0.1527(4) 0.4168(3) -0.1912(4) 0.0201(7) Uani 1 1 d . . . . .
H17 H 0.1151 0.3617 -0.2792 0.024 Uiso 1 1 calc R U . . .
C18 C 0.5166(4) 0.8214(3) 0.4147(3) 0.0166(7) Uani 1 1 d . . . . .
C19 C -0.0031(4) 0.6258(3) -0.2615(3) 0.0205(7) Uani 1 1 d . . . . .
C20 C 0.2506(4) 0.3553(3) -0.0922(4) 0.0205(8) Uani 1 1 d . . . . .
H20 H 0.2798 0.2571 -0.1118 0.025 Uiso 1 1 calc R U . . .
C21 C 0.2051(5) 0.8125(3) 0.4443(3) 0.0222(8) Uani 1 1 d . . . . .
H21 H 0.1138 0.7834 0.4917 0.027 Uiso 1 1 calc R U . . .


_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
Br1 C9 1.898(3) . ?
S2 O3 1.620(2) . ?
S2 O4 1.429(2) . ?
S2 O5 1.430(2) . ?
S2 C7 1.773(3) . ?
O3 C8 1.415(3) . ?
O6 H6 0.8400 . ?
O6 C18 1.364(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C15 1.504(4) . ?
C8 C12 1.368(4) . ?
C8 C14 1.398(4) . ?
C9 C18 1.392(5) . ?
C9 C21 1.388(5) . ?
C10 H10 0.9500 . ?
C10 C15 1.391(4) . ?
C10 C18 1.392(4) . ?
C11 H11 0.9500 . ?
C11 C15 1.392(5) . ?
C11 C21 1.386(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(4) . ?
C13 H13 0.9500 . ?
C13 C20 1.378(5) . ?
C14 C17 1.402(4) . ?
C14 C19 1.437(4) . ?
N16 C19 1.144(4) . ?
C17 H17 0.9500 . ?
C17 C20 1.371(5) . ?
C20 H20 0.9500 . ?
C21 H21 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
O3 S2 C7 100.46(14) . . ?
O4 S2 O3 108.06(11) . . ?
O4 S2 O5 119.39(13) . . ?
O4 S2 C7 111.45(14) . . ?
O5 S2 O3 106.40(12) . . ?
O5 S2 C7 109.24(14) . . ?
C8 O3 S2 117.98(18) . . ?
C18 O6 H6 109.5 . . ?
S2 C7 H7A 109.0 . . ?
S2 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C15 C7 S2 113.0(2) . . ?
C15 C7 H7A 109.0 . . ?
C15 C7 H7B 109.0 . . ?
C12 C8 O3 121.2(3) . . ?
C12 C8 C14 122.0(3) . . ?
C14 C8 O3 116.8(3) . . ?
C18 C9 Br1 119.4(2) . . ?
C21 C9 Br1 119.1(3) . . ?
C21 C9 C18 121.5(3) . . ?
C15 C10 H10 119.7 . . ?
C15 C10 C18 120.7(3) . . ?
C18 C10 H10 119.7 . . ?
C15 C11 H11 120.1 . . ?
C21 C11 H11 120.1 . . ?
C21 C11 C15 119.9(3) . . ?
C8 C12 H12 120.7 . . ?
C8 C12 C13 118.5(3) . . ?
C13 C12 H12 120.7 . . ?
C12 C13 H13 119.6 . . ?
C20 C13 C12 120.8(3) . . ?
C20 C13 H13 119.6 . . ?
C8 C14 C17 118.3(3) . . ?
C8 C14 C19 121.0(3) . . ?
C17 C14 C19 120.6(3) . . ?
C10 C15 C7 120.1(3) . . ?
C10 C15 C11 120.1(3) . . ?
C11 C15 C7 119.8(3) . . ?
C14 C17 H17 120.1 . . ?
C20 C17 C14 119.7(3) . . ?
C20 C17 H17 120.1 . . ?
O6 C18 C9 125.0(3) . . ?
O6 C18 C10 116.7(3) . . ?
C9 C18 C10 118.4(3) . . ?
N16 C19 C14 179.3(4) . . ?
C13 C20 H20 119.7 . . ?
C17 C20 C13 120.7(3) . . ?
C17 C20 H20 119.7 . . ?
C9 C21 H21 120.3 . . ?
C11 C21 C9 119.5(3) . . ?
C11 C21 H21 120.3 . . ?

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
Br1 C9 C18 O6 0.8(4) . . . . ?
Br1 C9 C18 C10 -178.8(2) . . . . ?
Br1 C9 C21 C11 179.6(2) . . . . ?
S2 O3 C8 C12 79.7(3) . . . . ?
S2 O3 C8 C14 -103.1(3) . . . . ?
S2 C7 C15 C10 75.7(3) . . . . ?
S2 C7 C15 C11 -103.2(3) . . . . ?
O3 S2 C7 C15 58.7(2) . . . . ?
O3 C8 C12 C13 177.8(3) . . . . ?
O3 C8 C14 C17 -178.3(3) . . . . ?
O3 C8 C14 C19 -1.1(5) . . . . ?
O4 S2 O3 C8 -9.7(2) . . . . ?
O4 S2 C7 C15 -55.6(3) . . . . ?
O5 S2 O3 C8 119.7(2) . . . . ?
O5 S2 C7 C15 170.3(2) . . . . ?
C7 S2 O3 C8 -126.5(2) . . . . ?
C8 C12 C13 C20 -0.2(5) . . . . ?
C8 C14 C17 C20 1.0(5) . . . . ?
C12 C8 C14 C17 -1.1(5) . . . . ?
C12 C8 C14 C19 176.1(3) . . . . ?
C12 C13 C20 C17 0.2(5) . . . . ?
C14 C8 C12 C13 0.7(5) . . . . ?
C14 C17 C20 C13 -0.5(5) . . . . ?
C15 C10 C18 O6 179.7(3) . . . . ?
C15 C10 C18 C9 -0.7(4) . . . . ?
C15 C11 C21 C9 -0.8(5) . . . . ?
C18 C9 C21 C11 1.5(5) . . . . ?
C18 C10 C15 C7 -177.6(3) . . . . ?
C18 C10 C15 C11 1.3(4) . . . . ?
C19 C14 C17 C20 -176.2(3) . . . . ?
C21 C9 C18 O6 178.9(3) . . . . ?
C21 C9 C18 C10 -0.7(5) . . . . ?
C21 C11 C15 C7 178.3(3) . . . . ?
C21 C11 C15 C10 -0.5(4) . . . . ?

_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.280
_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.
;
_shelxl_version_number           2012-9
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1417522'
_audit_update_record             
;
2015-08-07 deposited with the CCDC.
2016-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 F N O5 S'
_chemical_formula_weight         349.33

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'
F F 0.0171 0.0103 '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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   8.087(2)
_cell_length_b                   8.590(3)
_cell_length_c                   11.637(4)
_cell_angle_alpha                87.857(13)
_cell_angle_beta                 79.184(11)
_cell_angle_gamma                79.188(12)
_cell_volume                     779.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9526
_exptl_absorpt_correction_T_max  0.9526
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2508
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1928
_reflns_number_gt                1578
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0800P)²+0.1791P] 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         1928
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
S1 S 0.85119(9) 0.59130(8) 0.66942(5) 0.0194(3) Uani 1 1 d . . .
F3 F 0.5553(2) 1.2973(2) 0.48541(14) 0.0353(6) Uani 1 1 d . . .
O2 O 1.0012(2) 0.4383(2) 0.67297(14) 0.0221(6) Uani 1 1 d . . .
O4 O 0.7528(2) 0.5415(2) 0.59326(15) 0.0259(6) Uani 1 1 d . . .
O5 O 0.7734(2) 0.6384(2) 0.78662(15) 0.0255(6) Uani 1 1 d . . .
O7 O 0.6053(3) 1.0391(3) 0.34429(15) 0.0307(6) Uani 1 1 d . . .
O13 O 0.8317(3) 1.1051(3) 0.22514(17) 0.0443(8) Uani 1 1 d . . .
N9 N 0.7595(4) 0.2532(3) 0.8956(2) 0.0330(8) Uani 1 1 d . . .
C6 C 1.1031(4) 0.4260(3) 0.7602(2) 0.0215(8) Uani 1 1 d . . .
C10 C 0.7847(3) 0.8927(4) 0.4704(2) 0.0220(8) Uani 1 1 d . . .
H10 H 0.8070 0.8031 0.4207 0.026 Uiso 1 1 calc R . .
C11 C 0.7139(4) 1.1542(4) 0.6182(2) 0.0234(8) Uani 1 1 d . . .
H11 H 0.6880 1.2433 0.6686 0.028 Uiso 1 1 calc R . .
C12 C 1.1516(4) 0.3296(4) 0.9502(2) 0.0279(9) Uani 1 1 d . . .
H12 H 1.1151 0.2815 1.0231 0.034 Uiso 1 1 calc R . .
C14 C 0.6918(4) 1.0741(3) 0.2378(2) 0.0229(8) Uani 1 1 d . . .
C15 C 0.8872(4) 0.2971(4) 0.8832(2) 0.0238(8) Uani 1 1 d . . .
C16 C 0.6852(4) 1.0331(4) 0.4419(2) 0.0225(8) Uani 1 1 d . . .
C17 C 0.9689(4) 0.7351(3) 0.6008(2) 0.0191(7) Uani 1 1 d . . .
H17A H 1.0432 0.7611 0.6532 0.023 Uiso 1 1 calc R . .
H17B H 1.0435 0.6905 0.5277 0.023 Uiso 1 1 calc R . .
C18 C 0.8146(4) 1.0133(3) 0.6466(2) 0.0202(7) Uani 1 1 d . . .
H18 H 0.8581 1.0060 0.7174 0.024 Uiso 1 1 calc R . .
C19 C 1.0475(4) 0.3506(3) 0.8651(2) 0.0212(8) Uani 1 1 d . . .
C20 C 1.2591(4) 0.4730(4) 0.7368(2) 0.0262(8) Uani 1 1 d . . .
H20 H 1.2969 0.5194 0.6634 0.031 Uiso 1 1 calc R . .
C21 C 0.5874(4) 1.0663(4) 0.1463(2) 0.0282(8) Uani 1 1 d . . .
H21A H 0.4774 1.0383 0.1826 0.034 Uiso 1 1 calc R . .
H21B H 0.6488 0.9858 0.0883 0.034 Uiso 1 1 calc R . .
H21C H 0.5674 1.1697 0.1077 0.034 Uiso 1 1 calc R . .
C22 C 0.6526(4) 1.1607(4) 0.5151(2) 0.0243(8) Uani 1 1 d . . .
C23 C 1.3610(4) 0.4518(4) 0.8218(2) 0.0308(9) Uani 1 1 d . . .
H23 H 1.4677 0.4867 0.8079 0.037 Uiso 1 1 calc R . .
C24 C 1.3061(4) 0.3788(4) 0.9278(2) 0.0321(9) Uani 1 1 d . . .
H24 H 1.3771 0.3631 0.9853 0.039 Uiso 1 1 calc R . .
C25 C 0.8519(3) 0.8844(3) 0.5728(2) 0.0206(7) Uani 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
S1 O4 1.422(2) . ?
S1 O5 1.4295(18) . ?
S1 O2 1.6179(18) . ?
S1 C17 1.775(3) . ?
F3 C22 1.357(3) . ?
O2 C6 1.412(4) . ?
O7 C14 1.357(3) . ?
O7 C16 1.403(4) . ?
O13 C14 1.192(4) . ?
N9 C15 1.147(4) . ?
C6 C20 1.372(5) . ?
C6 C19 1.399(4) . ?
C10 C16 1.385(4) . ?
C10 C25 1.393(4) . ?
C10 H10 0.9500 . ?
C11 C22 1.377(4) . ?
C11 C18 1.392(4) . ?
C11 H11 0.9500 . ?
C12 C24 1.370(5) . ?
C12 C19 1.402(4) . ?
C12 H12 0.9500 . ?
C14 C21 1.488(4) . ?
C15 C19 1.432(5) . ?
C16 C22 1.369(4) . ?
C17 C25 1.508(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C25 1.380(4) . ?
C18 H18 0.9500 . ?
C20 C23 1.388(4) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C23 C24 1.398(4) . ?
C23 H23 0.9500 . ?
C24 H24 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
O4 S1 O5 120.28(12) . . ?
O4 S1 O2 102.70(12) . . ?
O5 S1 O2 108.98(9) . . ?
O4 S1 C17 111.04(13) . . ?
O5 S1 C17 110.13(13) . . ?
O2 S1 C17 101.81(12) . . ?
C6 O2 S1 119.96(17) . . ?
C14 O7 C16 119.1(2) . . ?
C20 C6 C19 121.8(3) . . ?
C20 C6 O2 120.1(2) . . ?
C19 C6 O2 117.7(3) . . ?
C16 C10 C25 119.3(3) . . ?
C16 C10 H10 120.3 . . ?
C25 C10 H10 120.3 . . ?
C22 C11 C18 118.2(3) . . ?
C22 C11 H11 120.9 . . ?
C18 C11 H11 120.9 . . ?
C24 C12 C19 119.7(3) . . ?
C24 C12 H12 120.2 . . ?
C19 C12 H12 120.2 . . ?
O13 C14 O7 122.0(3) . . ?
O13 C14 C21 127.8(2) . . ?
O7 C14 C21 110.3(3) . . ?
N9 C15 C19 178.7(3) . . ?
C22 C16 C10 119.7(3) . . ?
C22 C16 O7 120.3(2) . . ?
C10 C16 O7 119.8(3) . . ?
C25 C17 S1 111.54(19) . . ?
C25 C17 H17A 109.3 . . ?
S1 C17 H17A 109.3 . . ?
C25 C17 H17B 109.3 . . ?
S1 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C25 C18 C11 120.6(3) . . ?
C25 C18 H18 119.7 . . ?
C11 C18 H18 119.7 . . ?
C6 C19 C12 118.6(3) . . ?
C6 C19 C15 119.7(3) . . ?
C12 C19 C15 121.7(2) . . ?
C6 C20 C23 119.0(3) . . ?
C6 C20 H20 120.5 . . ?
C23 C20 H20 120.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F3 C22 C16 118.8(3) . . ?
F3 C22 C11 119.1(3) . . ?
C16 C22 C11 122.1(2) . . ?
C20 C23 C24 119.8(3) . . ?
C20 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C12 C24 C23 121.0(3) . . ?
C12 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C18 C25 C10 120.1(2) . . ?
C18 C25 C17 120.3(2) . . ?
C10 C25 C17 119.6(3) . . ?

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
O4 S1 O2 C6 -165.3(2) . . . . ?
O5 S1 O2 C6 -36.7(2) . . . . ?
C17 S1 O2 C6 79.7(2) . . . . ?
S1 O2 C6 C20 -96.0(3) . . . . ?
S1 O2 C6 C19 90.2(3) . . . . ?
C16 O7 C14 O13 -2.5(4) . . . . ?
C16 O7 C14 C21 177.2(2) . . . . ?
C25 C10 C16 C22 -0.8(4) . . . . ?
C25 C10 C16 O7 -174.7(2) . . . . ?
C14 O7 C16 C22 97.9(3) . . . . ?
C14 O7 C16 C10 -88.1(3) . . . . ?
O4 S1 C17 C25 63.6(2) . . . . ?
O5 S1 C17 C25 -72.2(2) . . . . ?
O2 S1 C17 C25 172.28(19) . . . . ?
C22 C11 C18 C25 0.1(4) . . . . ?
C20 C6 C19 C12 2.9(4) . . . . ?
O2 C6 C19 C12 176.6(2) . . . . ?
C20 C6 C19 C15 -177.1(3) . . . . ?
O2 C6 C19 C15 -3.4(4) . . . . ?
C24 C12 C19 C6 -1.8(4) . . . . ?
C24 C12 C19 C15 178.2(3) . . . . ?
N9 C15 C19 C6 41(14) . . . . ?
N9 C15 C19 C12 -139(14) . . . . ?
C19 C6 C20 C23 -3.0(4) . . . . ?
O2 C6 C20 C23 -176.5(2) . . . . ?
C10 C16 C22 F3 179.8(2) . . . . ?
O7 C16 C22 F3 -6.3(4) . . . . ?
C10 C16 C22 C11 -0.9(5) . . . . ?
O7 C16 C22 C11 173.0(3) . . . . ?
C18 C11 C22 F3 -179.5(2) . . . . ?
C18 C11 C22 C16 1.2(4) . . . . ?
C6 C20 C23 C24 2.0(4) . . . . ?
C19 C12 C24 C23 0.9(5) . . . . ?
C20 C23 C24 C12 -0.9(5) . . . . ?
C11 C18 C25 C10 -1.8(4) . . . . ?
C11 C18 C25 C17 176.7(2) . . . . ?
C16 C10 C25 C18 2.1(4) . . . . ?
C16 C10 C25 C17 -176.4(2) . . . . ?
S1 C17 C25 C18 98.0(3) . . . . ?
S1 C17 C25 C10 -83.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.701
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.701
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1417523'
_audit_update_record             
;
2015-08-07 deposited with the CCDC.
2016-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Cl2 N O5 S'
_chemical_formula_weight         401.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   5.327(3)
_cell_length_b                   15.367(10)
_cell_length_c                   19.690(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1611.8(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             820
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8960
_exptl_absorpt_correction_T_max  0.8960
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12367
_diffrn_reflns_av_R_equivalents  0.1009
_diffrn_reflns_av_sigmaI/netI    0.0903
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2824
_reflns_number_gt                2568
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0688P)²+0.8403P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(14)
_refine_ls_number_reflns         2824
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1530
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_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 0.3192(3) -0.01360(10) 0.18204(7) 0.0167(4) Uani 1 1 d . . .
Cl26 Cl 0.4141(3) 0.08099(10) 0.04124(7) 0.0187(4) Uani 1 1 d . . .
S3 S 0.0179(3) 0.10921(10) 0.33586(7) 0.0137(4) Uani 1 1 d . . .
O2 O 0.2844(8) 0.1192(3) 0.3277(2) 0.0208(10) Uani 1 1 d . . .
O4 O -0.1228(8) 0.3769(3) 0.1607(2) 0.0212(10) Uani 1 1 d . . .
O5 O -0.1118(8) 0.2022(2) 0.32312(19) 0.0134(9) Uani 1 1 d . . .
O6 O -0.0741(8) 0.0738(3) 0.39828(19) 0.0186(10) Uani 1 1 d . . .
O7 O -0.3249(9) 0.2780(3) 0.0959(2) 0.0175(10) Uani 1 1 d . . .
N9 N 0.4060(10) 0.3174(4) 0.2581(3) 0.0216(13) Uani 1 1 d . . .
C8 C -0.0629(11) 0.1002(4) 0.1994(3) 0.0119(13) Uani 1 1 d . . .
C10 C -0.2439(11) 0.2741(4) 0.4263(3) 0.0157(14) Uani 1 1 d . . .
H10 H -0.3815 0.2351 0.4301 0.019 Uiso 1 1 calc R . .
C11 C 0.1256(12) 0.3246(4) 0.3651(3) 0.0168(14) Uani 1 1 d . . .
C12 C -0.1225(11) 0.0560(4) 0.2659(3) 0.0138(14) Uani 1 1 d . . .
H12A H -0.0626 -0.0049 0.2642 0.017 Uiso 1 1 calc R . .
H12B H -0.3067 0.0549 0.2724 0.017 Uiso 1 1 calc R . .
C13 C -0.2972(12) 0.3591(4) 0.1249(3) 0.0136(14) Uani 1 1 d . . .
C14 C -0.0041(12) 0.3960(4) 0.4690(3) 0.0206(15) Uani 1 1 d . . .
H14 H 0.0218 0.4396 0.5025 0.025 Uiso 1 1 calc R . .
C16 C 0.1342(11) 0.0742(4) 0.1580(3) 0.0134(13) Uani 1 1 d . . .
C17 C -0.0757(12) 0.2673(4) 0.3736(3) 0.0159(14) Uani 1 1 d . . .
C18 C 0.1823(12) 0.1163(4) 0.0957(3) 0.0164(14) Uani 1 1 d . . .
C19 C -0.2125(11) 0.1701(4) 0.1786(3) 0.0143(13) Uani 1 1 d . . .
H19 H -0.3500 0.1884 0.2058 0.017 Uiso 1 1 calc R . .
C20 C -0.1589(12) 0.2127(4) 0.1179(3) 0.0139(14) Uani 1 1 d . . .
C21 C 0.0337(11) 0.1869(4) 0.0761(3) 0.0146(13) Uani 1 1 d . . .
H21 H 0.0652 0.2164 0.0345 0.018 Uiso 1 1 calc R . .
C22 C 0.2818(12) 0.3200(4) 0.3056(3) 0.0163(14) Uani 1 1 d . . .
C23 C -0.5129(12) 0.4153(4) 0.1055(3) 0.0184(14) Uani 1 1 d . . .
H23A H -0.5513 0.4068 0.0572 0.022 Uiso 1 1 calc R . .
H23B H -0.4698 0.4764 0.1135 0.022 Uiso 1 1 calc R . .
H23C H -0.6598 0.3996 0.1328 0.022 Uiso 1 1 calc R . .
C24 C 0.1614(13) 0.3881(4) 0.4145(3) 0.0181(14) Uani 1 1 d . . .
H24 H 0.3004 0.4266 0.4110 0.022 Uiso 1 1 calc R . .
C25 C -0.2066(12) 0.3398(4) 0.4740(3) 0.0192(15) Uani 1 1 d . . .
H25 H -0.3218 0.3461 0.5105 0.023 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 C16 1.736(6) . ?
Cl26 C18 1.724(6) . ?
S3 O6 1.431(4) . ?
S3 O2 1.437(4) . ?
S3 O5 1.607(4) . ?
S3 C12 1.767(6) . ?
O4 C13 1.199(7) . ?
O5 C17 1.423(7) . ?
O7 C13 1.377(7) . ?
O7 C20 1.406(7) . ?
N9 C22 1.147(8) . ?
C8 C16 1.387(8) . ?
C8 C19 1.398(8) . ?
C8 C12 1.509(7) . ?
C10 C17 1.375(8) . ?
C10 C25 1.393(8) . ?
C10 H10 0.9500 . ?
C11 C24 1.391(9) . ?
C11 C17 1.397(9) . ?
C11 C22 1.438(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C23 1.487(9) . ?
C14 C25 1.386(9) . ?
C14 C24 1.395(8) . ?
C14 H14 0.9500 . ?
C16 C18 1.411(8) . ?
C18 C21 1.397(9) . ?
C19 C20 1.393(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(8) . ?
C21 H21 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24 0.9500 . ?
C25 H25 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
O6 S3 O2 118.4(3) . . ?
O6 S3 O5 109.0(2) . . ?
O2 S3 O5 108.2(3) . . ?
O6 S3 C12 110.4(3) . . ?
O2 S3 C12 112.4(3) . . ?
O5 S3 C12 96.2(3) . . ?
C17 O5 S3 117.3(4) . . ?
C13 O7 C20 116.8(5) . . ?
C16 C8 C19 118.7(5) . . ?
C16 C8 C12 122.6(6) . . ?
C19 C8 C12 118.6(5) . . ?
C17 C10 C25 118.1(6) . . ?
C17 C10 H10 120.9 . . ?
C25 C10 H10 120.9 . . ?
C24 C11 C17 117.6(6) . . ?
C24 C11 C22 121.6(6) . . ?
C17 C11 C22 120.7(6) . . ?
C8 C12 S3 112.3(4) . . ?
C8 C12 H12A 109.1 . . ?
S3 C12 H12A 109.1 . . ?
C8 C12 H12B 109.1 . . ?
S3 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
O4 C13 O7 122.2(6) . . ?
O4 C13 C23 128.1(6) . . ?
O7 C13 C23 109.6(5) . . ?
C25 C14 C24 119.5(6) . . ?
C25 C14 H14 120.2 . . ?
C24 C14 H14 120.2 . . ?
C8 C16 C18 121.0(6) . . ?
C8 C16 Cl1 119.6(5) . . ?
C18 C16 Cl1 119.4(5) . . ?
C10 C17 C11 122.8(6) . . ?
C10 C17 O5 119.5(6) . . ?
C11 C17 O5 117.6(5) . . ?
C21 C18 C16 119.6(6) . . ?
C21 C18 Cl26 118.5(4) . . ?
C16 C18 Cl26 121.8(5) . . ?
C20 C19 C8 119.7(6) . . ?
C20 C19 H19 120.1 . . ?
C8 C19 H19 120.1 . . ?
C21 C20 C19 122.1(6) . . ?
C21 C20 O7 119.4(5) . . ?
C19 C20 O7 118.1(5) . . ?
C20 C21 C18 118.7(5) . . ?
C20 C21 H21 120.6 . . ?
C18 C21 H21 120.6 . . ?
N9 C22 C11 179.1(7) . . ?
C13 C23 H23A 109.5 . . ?
C13 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C13 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11 C24 C14 120.8(6) . . ?
C11 C24 H24 119.6 . . ?
C14 C24 H24 119.6 . . ?
C14 C25 C10 121.0(6) . . ?
C14 C25 H25 119.5 . . ?
C10 C25 H25 119.5 . . ?

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
O6 S3 O5 C17 58.8(5) . . . . ?
O2 S3 O5 C17 -71.1(5) . . . . ?
C12 S3 O5 C17 172.9(4) . . . . ?
C16 C8 C12 S3 94.8(6) . . . . ?
C19 C8 C12 S3 -85.2(6) . . . . ?
O6 S3 C12 C8 171.0(4) . . . . ?
O2 S3 C12 C8 -54.5(5) . . . . ?
O5 S3 C12 C8 58.1(5) . . . . ?
C20 O7 C13 O4 8.9(8) . . . . ?
C20 O7 C13 C23 -170.0(5) . . . . ?
C19 C8 C16 C18 -0.8(9) . . . . ?
C12 C8 C16 C18 179.2(5) . . . . ?
C19 C8 C16 Cl1 -178.9(4) . . . . ?
C12 C8 C16 Cl1 1.1(8) . . . . ?
C25 C10 C17 C11 -1.7(9) . . . . ?
C25 C10 C17 O5 -178.5(5) . . . . ?
C24 C11 C17 C10 3.3(10) . . . . ?
C22 C11 C17 C10 -173.9(6) . . . . ?
C24 C11 C17 O5 -179.9(5) . . . . ?
C22 C11 C17 O5 3.0(9) . . . . ?
S3 O5 C17 C10 -90.3(6) . . . . ?
S3 O5 C17 C11 92.7(6) . . . . ?
C8 C16 C18 C21 1.7(9) . . . . ?
Cl1 C16 C18 C21 179.9(5) . . . . ?
C8 C16 C18 Cl26 -176.0(5) . . . . ?
Cl1 C16 C18 Cl26 2.1(7) . . . . ?
C16 C8 C19 C20 -1.0(9) . . . . ?
C12 C8 C19 C20 179.0(5) . . . . ?
C8 C19 C20 C21 1.9(9) . . . . ?
C8 C19 C20 O7 174.9(5) . . . . ?
C13 O7 C20 C21 -105.5(6) . . . . ?
C13 O7 C20 C19 81.2(7) . . . . ?
C19 C20 C21 C18 -1.0(9) . . . . ?
O7 C20 C21 C18 -173.9(5) . . . . ?
C16 C18 C21 C20 -0.8(9) . . . . ?
Cl26 C18 C21 C20 177.0(5) . . . . ?
C24 C11 C22 N9 -49(45) . . . . ?
C17 C11 C22 N9 128(45) . . . . ?
C17 C11 C24 C14 -2.4(9) . . . . ?
C22 C11 C24 C14 174.8(6) . . . . ?
C25 C14 C24 C11 0.0(9) . . . . ?
C24 C14 C25 C10 1.6(9) . . . . ?
C17 C10 C25 C14 -0.8(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.142
