# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_a
_database_code_depnum_ccdc_archive 'CCDC 1430129'
_audit_update_record             
;
2015-10-08 deposited with the CCDC.
2016-01-25 downloaded from the CCDC.
;
_audit_creation_date             2014-08-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H14 Br N O3 S'
_chemical_formula_sum            'C13 H14 Br N O3 S'
_chemical_formula_weight         344.22
_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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.218(4)
_cell_length_b                   9.2121(19)
_cell_length_c                   15.306(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.315(4)
_cell_angle_gamma                90
_cell_volume                     2838.6(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8530
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4840
_cell_measurement_theta_min      1.3361
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.046
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19717
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         1.011
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             6851
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0654
_diffrn_orient_matrix_UB_12      0.0054
_diffrn_orient_matrix_UB_13      0.0021
_diffrn_orient_matrix_UB_21      -0.0050
_diffrn_orient_matrix_UB_22      -0.0856
_diffrn_orient_matrix_UB_23      0.0666
_diffrn_orient_matrix_UB_31      -0.0008
_diffrn_orient_matrix_UB_32      0.0305
_diffrn_orient_matrix_UB_33      0.0392
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5796
_reflns_number_total             6448
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6448
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0243P)²+2.8076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0810
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1A(H1A), C2A(H2A), C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C3(H3A,H3B),
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A), C10(H10), C11(H11), C12(H12),
 C13(H13)
;
_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
Br1A Br -0.16607(2) 0.65085(3) 0.22934(2) 0.03714(8) Uani 1 1 d . . . . .
S1A S 0.13086(3) 0.70423(7) 0.33943(4) 0.02656(13) Uani 1 1 d . . . . .
O1A O -0.04030(8) 0.83376(19) 0.27837(11) 0.0271(4) Uani 1 1 d . . . . .
O2A O 0.14266(9) 0.5514(2) 0.34635(13) 0.0392(4) Uani 1 1 d . . . . .
O3A O 0.17339(8) 0.7982(2) 0.39381(11) 0.0337(4) Uani 1 1 d . . . . .
N1A N 0.05223(9) 0.7364(2) 0.35677(13) 0.0265(4) Uani 1 1 d . . . . .
C1A C -0.15136(11) 0.8055(3) 0.31770(16) 0.0261(5) Uani 1 1 d . . . . .
H1A H -0.1623 0.8991 0.2896 0.031 Uiso 1 1 calc R . . . .
C2A C -0.07916(11) 0.8068(3) 0.35297(15) 0.0245(5) Uani 1 1 d . . . . .
H2A H -0.0669 0.7125 0.3795 0.029 Uiso 1 1 calc R . . . .
C3A C -0.06580(12) 0.9268(3) 0.42069(18) 0.0328(6) Uani 1 1 d . . . . .
H3AA H -0.0746 1.0205 0.3931 0.039 Uiso 1 1 calc R . . . .
H3AB H -0.0195 0.9243 0.4438 0.039 Uiso 1 1 calc R . . . .
C4A C -0.10996(13) 0.9073(3) 0.49552(18) 0.0382(6) Uani 1 1 d . . . . .
H4AA H -0.0981 0.8181 0.5267 0.046 Uiso 1 1 calc R . . . .
H4AB H -0.1028 0.9873 0.5365 0.046 Uiso 1 1 calc R . . . .
C5A C -0.18267(12) 0.9019(3) 0.46062(19) 0.0366(6) Uani 1 1 d . . . . .
H5AA H -0.1957 0.9951 0.4350 0.044 Uiso 1 1 calc R . . . .
H5AB H -0.2096 0.8839 0.5088 0.044 Uiso 1 1 calc R . . . .
C6A C -0.19556(12) 0.7830(3) 0.39154(17) 0.0312(5) Uani 1 1 d . . . . .
H6AA H -0.1866 0.6888 0.4183 0.037 Uiso 1 1 calc R . . . .
H6AB H -0.2418 0.7854 0.3682 0.037 Uiso 1 1 calc R . . . .
C7A C 0.02228(11) 0.7939(3) 0.28690(16) 0.0242(5) Uani 1 1 d . . . . .
C8A C 0.06043(11) 0.8157(3) 0.21011(16) 0.0254(5) Uani 1 1 d . . . . .
C9A C 0.12487(12) 0.7659(3) 0.22958(15) 0.0255(5) Uani 1 1 d . . . . .
C10A C 0.17234(12) 0.7756(3) 0.17083(17) 0.0306(5) Uani 1 1 d . . . . .
H10A H 0.2155 0.7423 0.1848 0.037 Uiso 1 1 calc R . . . .
C11A C 0.15282(14) 0.8371(3) 0.09012(17) 0.0371(6) Uani 1 1 d . . . . .
H11A H 0.1835 0.8457 0.0487 0.045 Uiso 1 1 calc R . . . .
C12A C 0.08835(14) 0.8863(3) 0.06961(17) 0.0386(6) Uani 1 1 d . . . . .
H12A H 0.0767 0.9270 0.0147 0.046 Uiso 1 1 calc R . . . .
C13A C 0.04063(13) 0.8762(3) 0.12946(16) 0.0311(5) Uani 1 1 d . . . . .
H13A H -0.0026 0.9089 0.1157 0.037 Uiso 1 1 calc R . . . .
Br1 Br 0.34844(2) 0.53556(3) 0.19817(2) 0.04561(9) Uani 1 1 d . . . . .
S1 S 0.63903(3) 0.45484(6) 0.33008(4) 0.02285(12) Uani 1 1 d . . . . .
O1 O 0.46724(8) 0.33790(19) 0.25906(11) 0.0279(4) Uani 1 1 d . . . . .
O2 O 0.67905(8) 0.3591(2) 0.38671(11) 0.0304(4) Uani 1 1 d . . . . .
O3 O 0.65213(9) 0.60682(19) 0.33698(12) 0.0318(4) Uani 1 1 d . . . . .
N1 N 0.55960(9) 0.4243(2) 0.34330(13) 0.0249(4) Uani 1 1 d . . . . .
C1 C 0.35520(11) 0.3873(3) 0.29056(17) 0.0292(5) Uani 1 1 d . . . . .
H1 H 0.3405 0.2940 0.2647 0.035 Uiso 1 1 calc R . . . .
C2 C 0.42612(11) 0.3719(3) 0.33010(16) 0.0261(5) Uani 1 1 d . . . . .
H2 H 0.4410 0.4635 0.3580 0.031 Uiso 1 1 calc R . . . .
C3 C 0.43125(13) 0.2512(3) 0.39772(17) 0.0337(6) Uani 1 1 d . . . . .
H3A H 0.4770 0.2408 0.4221 0.040 Uiso 1 1 calc R . . . .
H3B H 0.4172 0.1602 0.3701 0.040 Uiso 1 1 calc R . . . .
C4 C 0.38738(14) 0.2868(4) 0.47092(19) 0.0443(7) Uani 1 1 d . . . . .
H4A H 0.3891 0.2073 0.5127 0.053 Uiso 1 1 calc R . . . .
H4B H 0.4040 0.3733 0.5017 0.053 Uiso 1 1 calc R . . . .
C5 C 0.31582(14) 0.3113(4) 0.4338(2) 0.0475(8) Uani 1 1 d . . . . .
H5A H 0.2974 0.2209 0.4100 0.057 Uiso 1 1 calc R . . . .
H5B H 0.2897 0.3415 0.4806 0.057 Uiso 1 1 calc R . . . .
C6 C 0.31102(13) 0.4263(3) 0.3622(2) 0.0440(7) Uani 1 1 d . . . . .
H6A H 0.2653 0.4344 0.3371 0.053 Uiso 1 1 calc R . . . .
H6B H 0.3245 0.5196 0.3873 0.053 Uiso 1 1 calc R . . . .
C7 C 0.53045(11) 0.3729(3) 0.27098(15) 0.0237(5) Uani 1 1 d . . . . .
C8 C 0.57021(11) 0.3534(3) 0.19557(15) 0.0240(5) Uani 1 1 d . . . . .
C9 C 0.63496(11) 0.3974(3) 0.21912(15) 0.0230(5) Uani 1 1 d . . . . .
C10 C 0.68338(12) 0.3946(3) 0.16147(16) 0.0284(5) Uani 1 1 d . . . . .
H10 H 0.7266 0.4252 0.1780 0.034 Uiso 1 1 calc R . . . .
C11 C 0.66451(13) 0.3435(3) 0.07701(17) 0.0341(6) Uani 1 1 d . . . . .
H11 H 0.6958 0.3396 0.0362 0.041 Uiso 1 1 calc R . . . .
C12 C 0.59969(13) 0.2982(3) 0.05269(17) 0.0368(6) Uani 1 1 d . . . . .
H12 H 0.5885 0.2638 -0.0039 0.044 Uiso 1 1 calc R . . . .
C13 C 0.55127(12) 0.3035(3) 0.11174(16) 0.0319(6) Uani 1 1 d . . . . .
H13 H 0.5078 0.2745 0.0954 0.038 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
Br1A C1A 1.968(2) . ?
S1A O2A 1.431(2) . ?
S1A O3A 1.4317(18) . ?
S1A N1A 1.662(2) . ?
S1A C9A 1.768(3) . ?
O1A C2A 1.466(3) . ?
O1A C7A 1.312(3) . ?
N1A C7A 1.293(3) . ?
C1A C2A 1.509(3) . ?
C1A C6A 1.518(3) . ?
C2A C3A 1.523(3) . ?
C3A C4A 1.527(4) . ?
C4A C5A 1.518(4) . ?
C5A C6A 1.528(4) . ?
C7A C8A 1.478(3) . ?
C8A C9A 1.387(3) . ?
C8A C13A 1.380(3) . ?
C9A C10A 1.377(3) . ?
C10A C11A 1.383(4) . ?
C11A C12A 1.388(4) . ?
C12A C13A 1.394(4) . ?
Br1 C1 1.962(3) . ?
S1 O2 1.4333(17) . ?
S1 O3 1.4269(18) . ?
S1 N1 1.661(2) . ?
S1 C9 1.774(2) . ?
O1 C2 1.463(3) . ?
O1 C7 1.314(3) . ?
N1 C7 1.295(3) . ?
C1 C2 1.510(3) . ?
C1 C6 1.520(4) . ?
C2 C3 1.516(4) . ?
C3 C4 1.527(4) . ?
C4 C5 1.521(4) . ?
C5 C6 1.521(5) . ?
C7 C8 1.477(3) . ?
C8 C9 1.386(3) . ?
C8 C13 1.383(3) . ?
C9 C10 1.378(3) . ?
C10 C11 1.395(4) . ?
C11 C12 1.393(4) . ?
C12 C13 1.393(4) . ?

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
O2A S1A O3A 117.72(12) . . ?
O2A S1A N1A 108.61(11) . . ?
O2A S1A C9A 112.52(12) . . ?
O3A S1A N1A 109.33(11) . . ?
O3A S1A C9A 110.06(11) . . ?
N1A S1A C9A 96.45(11) . . ?
C7A O1A C2A 117.16(18) . . ?
C7A N1A S1A 108.82(17) . . ?
C2A C1A Br1A 109.35(16) . . ?
C2A C1A C6A 110.6(2) . . ?
C6A C1A Br1A 110.57(16) . . ?
O1A C2A C1A 107.05(19) . . ?
O1A C2A C3A 109.44(19) . . ?
C1A C2A C3A 110.7(2) . . ?
C2A C3A C4A 110.2(2) . . ?
C5A C4A C3A 110.8(2) . . ?
C4A C5A C6A 111.4(2) . . ?
C1A C6A C5A 110.1(2) . . ?
O1A C7A C8A 116.9(2) . . ?
N1A C7A O1A 124.8(2) . . ?
N1A C7A C8A 118.3(2) . . ?
C9A C8A C7A 109.5(2) . . ?
C13A C8A C7A 129.5(2) . . ?
C13A C8A C9A 121.0(2) . . ?
C8A C9A S1A 106.90(18) . . ?
C10A C9A S1A 130.6(2) . . ?
C10A C9A C8A 122.4(2) . . ?
C9A C10A C11A 116.8(2) . . ?
C10A C11A C12A 121.3(2) . . ?
C11A C12A C13A 121.5(3) . . ?
C8A C13A C12A 117.0(2) . . ?
O2 S1 N1 108.67(10) . . ?
O2 S1 C9 111.66(11) . . ?
O3 S1 O2 117.94(11) . . ?
O3 S1 N1 109.39(11) . . ?
O3 S1 C9 110.82(11) . . ?
N1 S1 C9 96.11(10) . . ?
C7 O1 C2 117.17(18) . . ?
C7 N1 S1 109.05(16) . . ?
C2 C1 Br1 110.74(17) . . ?
C2 C1 C6 109.4(2) . . ?
C6 C1 Br1 110.42(19) . . ?
O1 C2 C1 107.82(19) . . ?
O1 C2 C3 110.0(2) . . ?
C1 C2 C3 110.2(2) . . ?
C2 C3 C4 109.6(2) . . ?
C5 C4 C3 110.8(2) . . ?
C6 C5 C4 111.6(2) . . ?
C1 C6 C5 110.7(2) . . ?
O1 C7 C8 117.0(2) . . ?
N1 C7 O1 124.6(2) . . ?
N1 C7 C8 118.3(2) . . ?
C9 C8 C7 109.3(2) . . ?
C13 C8 C7 129.9(2) . . ?
C13 C8 C9 120.8(2) . . ?
C8 C9 S1 107.17(17) . . ?
C10 C9 S1 130.27(18) . . ?
C10 C9 C8 122.6(2) . . ?
C9 C10 C11 116.8(2) . . ?
C12 C11 C10 121.2(2) . . ?
C11 C12 C13 121.1(2) . . ?
C8 C13 C12 117.6(2) . . ?

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
Br1A C1A C2A O1A 59.9(2) . . . . ?
Br1A C1A C2A C3A 179.17(17) . . . . ?
Br1A C1A C6A C5A 178.85(17) . . . . ?
S1A N1A C7A O1A -179.54(19) . . . . ?
S1A N1A C7A C8A 1.1(3) . . . . ?
S1A C9A C10A C11A -176.3(2) . . . . ?
O1A C2A C3A C4A 175.5(2) . . . . ?
O1A C7A C8A C9A -179.0(2) . . . . ?
O1A C7A C8A C13A 1.9(4) . . . . ?
O2A S1A N1A C7A -118.20(18) . . . . ?
O2A S1A C9A C8A 115.23(18) . . . . ?
O2A S1A C9A C10A -68.3(3) . . . . ?
O3A S1A N1A C7A 112.14(18) . . . . ?
O3A S1A C9A C8A -111.34(18) . . . . ?
O3A S1A C9A C10A 65.1(3) . . . . ?
N1A S1A C9A C8A 1.99(19) . . . . ?
N1A S1A C9A C10A 178.4(2) . . . . ?
N1A C7A C8A C9A 0.4(3) . . . . ?
N1A C7A C8A C13A -178.7(3) . . . . ?
C1A C2A C3A C4A 57.7(3) . . . . ?
C2A O1A C7A N1A -1.9(3) . . . . ?
C2A O1A C7A C8A 177.45(19) . . . . ?
C2A C1A C6A C5A 57.6(3) . . . . ?
C2A C3A C4A C5A -56.0(3) . . . . ?
C3A C4A C5A C6A 55.8(3) . . . . ?
C4A C5A C6A C1A -56.3(3) . . . . ?
C6A C1A C2A O1A -178.09(19) . . . . ?
C6A C1A C2A C3A -58.9(3) . . . . ?
C7A O1A C2A C1A -158.5(2) . . . . ?
C7A O1A C2A C3A 81.4(3) . . . . ?
C7A C8A C9A S1A -1.6(2) . . . . ?
C7A C8A C9A C10A -178.4(2) . . . . ?
C7A C8A C13A C12A 178.3(2) . . . . ?
C8A C9A C10A C11A -0.4(4) . . . . ?
C9A S1A N1A C7A -1.79(19) . . . . ?
C9A C8A C13A C12A -0.7(4) . . . . ?
C9A C10A C11A C12A -0.1(4) . . . . ?
C10A C11A C12A C13A 0.2(4) . . . . ?
C11A C12A C13A C8A 0.3(4) . . . . ?
C13A C8A C9A S1A 177.6(2) . . . . ?
C13A C8A C9A C10A 0.8(4) . . . . ?
Br1 C1 C2 O1 -56.7(2) . . . . ?
Br1 C1 C2 C3 -176.82(17) . . . . ?
Br1 C1 C6 C5 179.74(18) . . . . ?
S1 N1 C7 O1 -179.53(19) . . . . ?
S1 N1 C7 C8 -0.4(3) . . . . ?
S1 C9 C10 C11 -179.6(2) . . . . ?
O1 C2 C3 C4 -179.2(2) . . . . ?
O1 C7 C8 C9 179.1(2) . . . . ?
O1 C7 C8 C13 0.3(4) . . . . ?
O2 S1 N1 C7 -114.69(18) . . . . ?
O2 S1 C9 C8 112.19(17) . . . . ?
O2 S1 C9 C10 -68.7(3) . . . . ?
O3 S1 N1 C7 115.28(18) . . . . ?
O3 S1 C9 C8 -114.15(18) . . . . ?
O3 S1 C9 C10 65.0(3) . . . . ?
N1 S1 C9 C8 -0.70(18) . . . . ?
N1 S1 C9 C10 178.4(2) . . . . ?
N1 C7 C8 C9 -0.1(3) . . . . ?
N1 C7 C8 C13 -178.9(3) . . . . ?
C1 C2 C3 C4 -60.4(3) . . . . ?
C2 O1 C7 N1 5.7(3) . . . . ?
C2 O1 C7 C8 -173.4(2) . . . . ?
C2 C1 C6 C5 -58.1(3) . . . . ?
C2 C3 C4 C5 56.5(3) . . . . ?
C3 C4 C5 C6 -54.3(4) . . . . ?
C4 C5 C6 C1 55.1(3) . . . . ?
C6 C1 C2 O1 -178.7(2) . . . . ?
C6 C1 C2 C3 61.2(3) . . . . ?
C7 O1 C2 C1 155.0(2) . . . . ?
C7 O1 C2 C3 -84.8(2) . . . . ?
C7 C8 C9 S1 0.5(2) . . . . ?
C7 C8 C9 C10 -178.7(2) . . . . ?
C7 C8 C13 C12 179.1(3) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 S1 N1 C7 0.65(19) . . . . ?
C9 C8 C13 C12 0.5(4) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C11 C12 C13 C8 -0.8(4) . . . . ?
C13 C8 C9 S1 179.5(2) . . . . ?
C13 C8 C9 C10 0.3(4) . . . . ?

####################################################################### 
# 
# 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_sa3560
_database_code_depnum_ccdc_archive 'CCDC 1430132'
_audit_update_record             
;
2015-10-08 deposited with the CCDC.
2016-01-25 downloaded from the CCDC.
;
_audit_creation_date             2014-08-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H14 Br N O3 S'
_chemical_formula_sum            'C13 H14 Br N O3 S'
_chemical_formula_weight         344.22
_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'

_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.
;
_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                   7.8592(17)
_cell_length_b                   9.0905(18)
_cell_length_c                   9.748(2)
_cell_angle_alpha                79.190(7)
_cell_angle_beta                 89.100(8)
_cell_angle_gamma                77.310(6)
_cell_volume                     667.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2386
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4777
_cell_measurement_theta_min      2.6575
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.240
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8259
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         2.657
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             3050
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0319
_diffrn_orient_matrix_UB_12      -0.0802
_diffrn_orient_matrix_UB_13      -0.0978
_diffrn_orient_matrix_UB_21      -0.0435
_diffrn_orient_matrix_UB_22      0.1005
_diffrn_orient_matrix_UB_23      -0.0345
_diffrn_orient_matrix_UB_31      0.0964
_diffrn_orient_matrix_UB_32      0.0056
_diffrn_orient_matrix_UB_33      -0.0398
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2943
_reflns_number_total             3044
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3044
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0287P)²+0.3450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0632
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
;
_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 0.26588(2) 0.59971(2) 0.48315(2) 0.02735(7) Uani 1 1 d . . . . .
S1 S 0.05802(6) 0.71606(5) 0.07503(5) 0.02168(10) Uani 1 1 d . . . . .
O1 O 0.34871(18) 0.91556(16) 0.23809(15) 0.0283(3) Uani 1 1 d . . . . .
O2 O -0.07729(17) 0.81539(19) -0.01660(15) 0.0331(3) Uani 1 1 d . . . . .
O3 O 0.0253(2) 0.57297(17) 0.14603(15) 0.0319(3) Uani 1 1 d . . . . .
N1 N 0.12074(19) 0.80831(18) 0.19183(16) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.0173(2) 0.8447(2) 0.31361(19) 0.0205(3) Uani 1 1 d . . . . .
H1 H 0.0685 0.9170 0.3533 0.025 Uiso 1 1 calc R . . . .
C2 C -0.1723(2) 0.9231(2) 0.2720(2) 0.0259(4) Uani 1 1 d . . . . .
H2A H -0.2272 0.8537 0.2332 0.031 Uiso 1 1 calc R . . . .
H2B H -0.1755 1.0138 0.2006 0.031 Uiso 1 1 calc R . . . .
C3 C -0.2735(2) 0.9691(2) 0.3983(2) 0.0287(4) Uani 1 1 d . . . . .
H3A H -0.2255 1.0460 0.4315 0.034 Uiso 1 1 calc R . . . .
H3B H -0.3946 1.0140 0.3705 0.034 Uiso 1 1 calc R . . . .
C4 C -0.2639(3) 0.8313(2) 0.5154(2) 0.0301(4) Uani 1 1 d . . . . .
H4A H -0.3253 0.7604 0.4860 0.036 Uiso 1 1 calc R . . . .
H4B H -0.3216 0.8650 0.5964 0.036 Uiso 1 1 calc R . . . .
C5 C -0.0747(3) 0.7480(2) 0.5561(2) 0.0256(4) Uani 1 1 d . . . . .
H5A H -0.0166 0.8144 0.5962 0.031 Uiso 1 1 calc R . . . .
H5B H -0.0733 0.6564 0.6260 0.031 Uiso 1 1 calc R . . . .
C6 C 0.0221(2) 0.7039(2) 0.42843(19) 0.0209(3) Uani 1 1 d . . . . .
H6 H -0.0343 0.6324 0.3922 0.025 Uiso 1 1 calc R . . . .
C7 C 0.2839(2) 0.8449(2) 0.16813(19) 0.0211(3) Uani 1 1 d . . . . .
C8 C 0.3627(2) 0.7777(2) 0.04766(18) 0.0196(3) Uani 1 1 d . . . . .
C9 C 0.5249(2) 0.7864(2) -0.0078(2) 0.0242(4) Uani 1 1 d . . . . .
H9 H 0.5964 0.8395 0.0287 0.029 Uiso 1 1 calc R . . . .
C10 C 0.5772(2) 0.7137(2) -0.1194(2) 0.0270(4) Uani 1 1 d . . . . .
H10 H 0.6860 0.7170 -0.1572 0.032 Uiso 1 1 calc R . . . .
C11 C 0.4698(3) 0.6358(2) -0.1759(2) 0.0266(4) Uani 1 1 d . . . . .
H11 H 0.5080 0.5882 -0.2508 0.032 Uiso 1 1 calc R . . . .
C12 C 0.3057(2) 0.6280(2) -0.12197(19) 0.0251(4) Uani 1 1 d . . . . .
H12 H 0.2324 0.5775 -0.1598 0.030 Uiso 1 1 calc R . . . .
C13 C 0.2581(2) 0.6992(2) -0.00949(18) 0.0198(3) 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
Br1 C6 1.9746(18) . ?
S1 O2 1.4316(15) . ?
S1 O3 1.4285(15) . ?
S1 N1 1.6733(15) . ?
S1 C13 1.7536(18) . ?
O1 C7 1.207(2) . ?
N1 C1 1.476(2) . ?
N1 C7 1.399(2) . ?
C1 H1 0.9800 . ?
C1 C2 1.529(2) . ?
C1 C6 1.528(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.529(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.518(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.534(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.520(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.489(2) . ?
C8 C9 1.390(2) . ?
C8 C13 1.385(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.394(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.396(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 N1 110.93(9) . . ?
O2 S1 C13 109.77(9) . . ?
O3 S1 O2 117.34(9) . . ?
O3 S1 N1 109.19(8) . . ?
O3 S1 C13 113.87(9) . . ?
N1 S1 C13 93.11(8) . . ?
C1 N1 S1 123.58(12) . . ?
C7 N1 S1 114.64(12) . . ?
C7 N1 C1 121.75(14) . . ?
N1 C1 H1 107.5 . . ?
N1 C1 C2 111.89(15) . . ?
N1 C1 C6 112.90(14) . . ?
C2 C1 H1 107.5 . . ?
C2 C1 C6 109.42(15) . . ?
C6 C1 H1 107.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 C3 110.84(16) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.07(16) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C3 C4 C5 111.77(16) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C4 110.20(16) . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
Br1 C6 H6 108.7 . . ?
C1 C6 Br1 110.20(12) . . ?
C1 C6 H6 108.7 . . ?
C5 C6 Br1 109.36(12) . . ?
C5 C6 C1 111.24(15) . . ?
C5 C6 H6 108.7 . . ?
O1 C7 N1 124.41(17) . . ?
O1 C7 C8 127.01(16) . . ?
N1 C7 C8 108.55(15) . . ?
C9 C8 C7 126.54(16) . . ?
C13 C8 C7 113.60(15) . . ?
C13 C8 C9 119.85(17) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 C8 118.08(17) . . ?
C10 C9 H9 121.0 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.23(17) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.10(18) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 121.8 . . ?
C13 C12 C11 116.47(17) . . ?
C13 C12 H12 121.8 . . ?
C8 C13 S1 109.73(13) . . ?
C12 C13 S1 126.91(14) . . ?
C12 C13 C8 123.25(16) . . ?

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
S1 N1 C1 C2 -50.2(2) . . . . ?
S1 N1 C1 C6 73.73(18) . . . . ?
S1 N1 C7 O1 177.47(15) . . . . ?
S1 N1 C7 C8 -4.50(18) . . . . ?
O1 C7 C8 C9 -1.2(3) . . . . ?
O1 C7 C8 C13 178.31(18) . . . . ?
O2 S1 N1 C1 75.23(16) . . . . ?
O2 S1 N1 C7 -106.78(14) . . . . ?
O2 S1 C13 C8 108.28(14) . . . . ?
O2 S1 C13 C12 -67.90(19) . . . . ?
O3 S1 N1 C1 -55.59(16) . . . . ?
O3 S1 N1 C7 122.39(14) . . . . ?
O3 S1 C13 C8 -117.87(14) . . . . ?
O3 S1 C13 C12 65.95(19) . . . . ?
N1 S1 C13 C8 -5.28(14) . . . . ?
N1 S1 C13 C12 178.54(17) . . . . ?
N1 C1 C2 C3 -176.22(15) . . . . ?
N1 C1 C6 Br1 54.31(17) . . . . ?
N1 C1 C6 C5 175.78(14) . . . . ?
N1 C7 C8 C9 -179.13(17) . . . . ?
N1 C7 C8 C13 0.3(2) . . . . ?
C1 N1 C7 O1 -4.5(3) . . . . ?
C1 N1 C7 C8 173.52(15) . . . . ?
C1 C2 C3 C4 -56.3(2) . . . . ?
C2 C1 C6 Br1 179.63(12) . . . . ?
C2 C1 C6 C5 -58.9(2) . . . . ?
C2 C3 C4 C5 54.7(2) . . . . ?
C3 C4 C5 C6 -55.0(2) . . . . ?
C4 C5 C6 Br1 179.19(13) . . . . ?
C4 C5 C6 C1 57.2(2) . . . . ?
C6 C1 C2 C3 57.9(2) . . . . ?
C7 N1 C1 C2 131.91(17) . . . . ?
C7 N1 C1 C6 -104.12(19) . . . . ?
C7 C8 C9 C10 178.86(17) . . . . ?
C7 C8 C13 S1 3.63(19) . . . . ?
C7 C8 C13 C12 179.98(16) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C9 C8 C13 S1 -176.85(14) . . . . ?
C9 C8 C13 C12 -0.5(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
C11 C12 C13 S1 176.94(14) . . . . ?
C11 C12 C13 C8 1.2(3) . . . . ?
C13 S1 N1 C1 -172.21(14) . . . . ?
C13 S1 N1 C7 5.77(14) . . . . ?
C13 C8 C9 C10 -0.6(3) . . . . ?

####################################################################### 
# 
# 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_sa3564
_database_code_depnum_ccdc_archive 'CCDC 1430133'
_audit_update_record             
;
2015-10-08 deposited with the CCDC.
2016-01-25 downloaded from the CCDC.
;
_audit_creation_date             2014-08-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H14 Br N O3 S'
_chemical_formula_sum            'C16 H14 Br N O3 S'
_chemical_formula_weight         380.25
_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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.830(2)
_cell_length_b                   9.2659(19)
_cell_length_c                   14.590(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.60(3)
_cell_angle_gamma                90
_cell_volume                     1585.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5307
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      31.4309
_cell_measurement_theta_min      2.1980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.736
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.52992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.619
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.212
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10495
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_min         2.611
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             3846
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0810
_diffrn_orient_matrix_UB_12      0.0258
_diffrn_orient_matrix_UB_13      -0.0066
_diffrn_orient_matrix_UB_21      0.0260
_diffrn_orient_matrix_UB_22      0.0938
_diffrn_orient_matrix_UB_23      0.0467
_diffrn_orient_matrix_UB_31      0.0049
_diffrn_orient_matrix_UB_32      0.0297
_diffrn_orient_matrix_UB_33      -0.0623
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3329
_reflns_number_total             3618
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3618
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.155
_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)+(0.0222P)²+1.4615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0807
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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 0.88179(2) 0.64653(3) 0.47358(2) 0.03240(9) Uani 1 1 d . . . . .
S1 S 0.69753(5) 1.01861(7) 0.77189(4) 0.02437(14) Uani 1 1 d . . . . .
O1 O 0.87718(14) 0.92290(18) 0.59173(11) 0.0222(4) Uani 1 1 d . . . . .
O2 O 0.73606(17) 1.1270(2) 0.83841(13) 0.0355(5) Uani 1 1 d . . . . .
O3 O 0.62580(17) 0.9072(2) 0.80010(15) 0.0383(5) Uani 1 1 d . . . . .
N1 N 0.80809(17) 0.9429(2) 0.73166(14) 0.0236(4) Uani 1 1 d . . . . .
C1 C 0.9616(2) 0.8168(3) 0.63404(16) 0.0222(5) Uani 1 1 d . . . . .
H1 H 0.9243 0.7474 0.6709 0.027 Uiso 1 1 calc R . . . .
C2 C 1.0579(2) 0.8901(3) 0.69439(17) 0.0217(5) Uani 1 1 d . . . . .
C3 C 1.0907(2) 0.8424(3) 0.78397(17) 0.0256(5) Uani 1 1 d . . . . .
H3 H 1.0499 0.7692 0.8083 0.031 Uiso 1 1 calc R . . . .
C4 C 1.1841(2) 0.9035(3) 0.83761(18) 0.0316(6) Uani 1 1 d . . . . .
H4 H 1.2055 0.8700 0.8975 0.038 Uiso 1 1 calc R . . . .
C5 C 1.2462(2) 1.0134(3) 0.80359(19) 0.0300(6) Uani 1 1 d . . . . .
C6 C 1.2115(2) 1.0629(3) 0.71405(19) 0.0299(6) Uani 1 1 d . . . . .
H6 H 1.2513 1.1377 0.6903 0.036 Uiso 1 1 calc R . . . .
C7 C 1.1188(2) 1.0023(3) 0.66011(17) 0.0258(5) Uani 1 1 d . . . . .
H7 H 1.0969 1.0366 0.6005 0.031 Uiso 1 1 calc R . . . .
C8 C 1.3487(3) 1.0777(4) 0.8621(2) 0.0447(8) Uani 1 1 d . . . . .
H8A H 1.3435 1.0601 0.9262 0.067 Uiso 1 1 calc GR . . . .
H8B H 1.3510 1.1798 0.8513 0.067 Uiso 1 1 calc GR . . . .
H8C H 1.4170 1.0340 0.8459 0.067 Uiso 1 1 calc GR . . . .
C9 C 1.0047(2) 0.7400(3) 0.55420(17) 0.0269(5) Uani 1 1 d . . . . .
H9A H 1.0604 0.6680 0.5781 0.032 Uiso 1 1 calc R . . . .
H9B H 1.0424 0.8091 0.5185 0.032 Uiso 1 1 calc R . . . .
C10 C 0.8028(2) 0.9708(2) 0.64449(16) 0.0208(5) Uani 1 1 d . . . . .
C11 C 0.7061(2) 1.0584(3) 0.59983(16) 0.0221(5) Uani 1 1 d . . . . .
C12 C 0.6367(2) 1.0949(3) 0.66547(17) 0.0238(5) Uani 1 1 d . . . . .
C13 C 0.5392(2) 1.1754(3) 0.6450(2) 0.0354(6) Uani 1 1 d . . . . .
H13 H 0.4933 1.1987 0.6900 0.043 Uiso 1 1 calc R . . . .
C14 C 0.5124(3) 1.2202(4) 0.5536(2) 0.0447(8) Uani 1 1 d . . . . .
H14 H 0.4471 1.2751 0.5368 0.054 Uiso 1 1 calc R . . . .
C15 C 0.5813(3) 1.1845(4) 0.4872(2) 0.0419(7) Uani 1 1 d . . . . .
H15 H 0.5612 1.2159 0.4267 0.050 Uiso 1 1 calc R . . . .
C16 C 0.6796(2) 1.1030(3) 0.50902(18) 0.0319(6) Uani 1 1 d . . . . .
H16 H 0.7258 1.0794 0.4644 0.038 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
Br1 C9 1.948(3) . ?
S1 O2 1.429(2) . ?
S1 O3 1.431(2) . ?
S1 N1 1.658(2) . ?
S1 C12 1.770(3) . ?
O1 C1 1.477(3) . ?
O1 C10 1.320(3) . ?
N1 C10 1.291(3) . ?
C1 C2 1.505(3) . ?
C1 C9 1.510(3) . ?
C2 C3 1.386(3) . ?
C2 C7 1.396(4) . ?
C3 C4 1.388(4) . ?
C4 C5 1.385(4) . ?
C5 C6 1.394(4) . ?
C5 C8 1.510(4) . ?
C6 C7 1.381(4) . ?
C10 C11 1.482(3) . ?
C11 C12 1.383(3) . ?
C11 C16 1.384(3) . ?
C12 C13 1.373(4) . ?
C13 C14 1.394(4) . ?
C14 C15 1.385(4) . ?
C15 C16 1.388(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 117.37(13) . . ?
O2 S1 N1 110.00(12) . . ?
O2 S1 C12 111.81(12) . . ?
O3 S1 N1 108.78(11) . . ?
O3 S1 C12 110.66(13) . . ?
N1 S1 C12 96.10(11) . . ?
C10 O1 C1 116.49(18) . . ?
C10 N1 S1 109.04(17) . . ?
O1 C1 C2 111.22(19) . . ?
O1 C1 C9 105.65(19) . . ?
C2 C1 C9 111.0(2) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 C7 118.8(2) . . ?
C7 C2 C1 120.9(2) . . ?
C2 C3 C4 120.3(2) . . ?
C5 C4 C3 121.2(3) . . ?
C4 C5 C6 118.3(2) . . ?
C4 C5 C8 120.8(3) . . ?
C6 C5 C8 121.0(3) . . ?
C7 C6 C5 120.9(3) . . ?
C6 C7 C2 120.5(2) . . ?
C1 C9 Br1 112.00(17) . . ?
O1 C10 C11 117.6(2) . . ?
N1 C10 O1 123.9(2) . . ?
N1 C10 C11 118.5(2) . . ?
C12 C11 C10 108.9(2) . . ?
C12 C11 C16 120.7(2) . . ?
C16 C11 C10 130.5(2) . . ?
C11 C12 S1 107.49(18) . . ?
C13 C12 S1 129.8(2) . . ?
C13 C12 C11 122.7(2) . . ?
C12 C13 C14 116.6(3) . . ?
C15 C14 C13 121.2(3) . . ?
C14 C15 C16 121.5(3) . . ?
C11 C16 C15 117.3(2) . . ?

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
S1 N1 C10 O1 -178.40(18) . . . . ?
S1 N1 C10 C11 -0.1(3) . . . . ?
S1 C12 C13 C14 -179.6(2) . . . . ?
O1 C1 C2 C3 129.6(2) . . . . ?
O1 C1 C2 C7 -53.3(3) . . . . ?
O1 C1 C9 Br1 -58.5(2) . . . . ?
O1 C10 C11 C12 178.5(2) . . . . ?
O1 C10 C11 C16 -1.3(4) . . . . ?
O2 S1 N1 C10 -115.79(18) . . . . ?
O2 S1 C12 C11 114.36(19) . . . . ?
O2 S1 C12 C13 -66.2(3) . . . . ?
O3 S1 N1 C10 114.37(19) . . . . ?
O3 S1 C12 C11 -112.79(19) . . . . ?
O3 S1 C12 C13 66.7(3) . . . . ?
N1 S1 C12 C11 -0.06(19) . . . . ?
N1 S1 C12 C13 179.4(3) . . . . ?
N1 C10 C11 C12 0.1(3) . . . . ?
N1 C10 C11 C16 -179.7(3) . . . . ?
C1 O1 C10 N1 8.0(3) . . . . ?
C1 O1 C10 C11 -170.35(19) . . . . ?
C1 C2 C3 C4 175.7(2) . . . . ?
C1 C2 C7 C6 -175.9(2) . . . . ?
C2 C1 C9 Br1 -179.11(16) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C2 C7 C6 1.2(4) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C3 C4 C5 C8 -179.1(3) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C5 C6 C7 C2 0.0(4) . . . . ?
C7 C2 C3 C4 -1.4(4) . . . . ?
C8 C5 C6 C7 178.9(3) . . . . ?
C9 C1 C2 C3 -113.1(3) . . . . ?
C9 C1 C2 C7 64.0(3) . . . . ?
C10 O1 C1 C2 -80.1(3) . . . . ?
C10 O1 C1 C9 159.4(2) . . . . ?
C10 C11 C12 S1 0.0(2) . . . . ?
C10 C11 C12 C13 -179.5(2) . . . . ?
C10 C11 C16 C15 179.5(3) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 S1 N1 C10 0.10(19) . . . . ?
C12 C11 C16 C15 -0.2(4) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C14 C15 C16 C11 0.1(5) . . . . ?
C16 C11 C12 S1 179.8(2) . . . . ?
C16 C11 C12 C13 0.2(4) . . . . ?

####################################################################### 
# 
# 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_sa3947
_database_code_depnum_ccdc_archive 'CCDC 1430134'
_audit_update_record             
;
2015-10-08 deposited with the CCDC.
2016-01-25 downloaded from the CCDC.
;
_audit_creation_date             2015-02-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Br N O3 S'
_chemical_formula_sum            'C16 H14 Br N O3 S'
_chemical_formula_weight         380.25
_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'

_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.
;
_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                   8.3045(15)
_cell_length_b                   9.415(2)
_cell_length_c                   11.190(2)
_cell_angle_alpha                87.089(10)
_cell_angle_beta                 73.797(9)
_cell_angle_gamma                70.74(7)
_cell_volume                     792.4(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2724
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4815
_cell_measurement_theta_min      2.2938
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.737
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10014
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.705
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 40.0801
	          2theta: -20.0701
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 40.0801
	          2theta: -20.0701
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 40.0801
	          2theta: -20.0701
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             3617
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0331
_diffrn_orient_matrix_UB_12      -0.0552
_diffrn_orient_matrix_UB_13      0.1162
_diffrn_orient_matrix_UB_21      -0.0342
_diffrn_orient_matrix_UB_22      -0.0669
_diffrn_orient_matrix_UB_23      -0.0839
_diffrn_orient_matrix_UB_31      0.0868
_diffrn_orient_matrix_UB_32      -0.0284
_diffrn_orient_matrix_UB_33      -0.0184
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3405
_reflns_number_total             3615
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'

;
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3615
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.148
_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)+(0.0357P)²+0.4345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0850
_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 C(H,H,H) groups
2. Restrained distances
 C16-C15
 1.54 with sigma of 0.01
 C16A-C15
 1.54 with sigma of 0.01
 C16A-Br1A
 2.8 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Br1A \\sim C16 \\sim C16A \\sim Br1: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.04
Uanis(C16) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C16A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(H15A)=Sof(Br1A)=Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(Br1)=Sof(H15)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
5.a Riding coordinates:
 C16A(H16D,H16E,H16F)
5.b Ternary CH refined with riding coordinates:
 C8(H8), C15(H15), C15(H15A)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 -0.04364(4) 0.82243(3) 0.05847(3) 0.04427(12) Uani 0.9303(12) 1 d . U P
A 1
S1 S 0.50278(6) 0.44755(5) 0.19995(4) 0.02127(12) Uani 1 1 d . . . . .
O1 O 0.4917(2) 0.35350(16) 0.10845(13) 0.0299(3) Uani 1 1 d . . . . .
O2 O 0.6343(2) 0.51957(18) 0.16355(15) 0.0334(3) Uani 1 1 d . . . . .
O3 O 0.0838(2) 0.64466(16) 0.44643(13) 0.0291(3) Uani 1 1 d . . . . .
N1 N 0.3032(2) 0.57599(17) 0.26106(14) 0.0196(3) Uani 1 1 d . . . . .
C1 C 0.5033(3) 0.3580(2) 0.34122(18) 0.0240(4) Uani 1 1 d . . . . .
C2 C 0.6321(3) 0.2307(3) 0.3623(2) 0.0366(5) Uani 1 1 d . . . . .
H2 H 0.7336 0.1816 0.2994 0.044 Uiso 1 1 calc R . . . .
C3 C 0.6017(4) 0.1798(3) 0.4830(3) 0.0440(6) Uani 1 1 d . . . . .
H3 H 0.6841 0.0934 0.5012 0.053 Uiso 1 1 calc R . . . .
C4 C 0.4508(4) 0.2553(3) 0.5768(2) 0.0405(6) Uani 1 1 d . . . . .
H4 H 0.4352 0.2198 0.6569 0.049 Uiso 1 1 calc R . . . .
C5 C 0.3234(3) 0.3826(3) 0.5528(2) 0.0315(5) Uani 1 1 d . . . . .
H5 H 0.2222 0.4327 0.6156 0.038 Uiso 1 1 calc R . . . .
C6 C 0.3509(3) 0.4334(2) 0.43280(18) 0.0229(4) Uani 1 1 d . . . . .
C7 C 0.2282(3) 0.5633(2) 0.38660(17) 0.0208(4) Uani 1 1 d . . . . .
C8 C 0.2232(2) 0.6922(2) 0.17981(17) 0.0204(4) Uani 1 1 d . . . . .
H8 H 0.3000 0.6647 0.0946 0.024 Uiso 1 1 calc R . . . .
C9 C 0.2270(3) 0.8455(2) 0.21392(18) 0.0231(4) Uani 1 1 d . . . . .
C10 C 0.3733(3) 0.8877(2) 0.1515(2) 0.0297(4) Uani 1 1 d . . . . .
H10 H 0.4635 0.8242 0.0888 0.036 Uiso 1 1 calc R . . . .
C11 C 0.3854(4) 1.0241(3) 0.1824(2) 0.0384(5) Uani 1 1 d . . . . .
H11 H 0.4836 1.0517 0.1407 0.046 Uiso 1 1 calc R . . . .
C12 C 0.2509(3) 1.1190(2) 0.2752(2) 0.0375(5) Uani 1 1 d . . . . .
H12 H 0.2590 1.2103 0.2960 0.045 Uiso 1 1 calc R . . . .
C13 C 0.1042(3) 1.0788(2) 0.3373(2) 0.0343(5) Uani 1 1 d . . . . .
H13 H 0.0138 1.1432 0.3994 0.041 Uiso 1 1 calc R . . . .
C14 C 0.0922(3) 0.9418(2) 0.3067(2) 0.0290(4) Uani 1 1 d . . . . .
H14 H -0.0063 0.9147 0.3485 0.035 Uiso 1 1 calc R . . . .
C15 C 0.0418(3) 0.6831(2) 0.18088(19) 0.0251(4) Uani 1 1 d D . . . .
H15 H -0.0411 0.7154 0.2637 0.030 Uiso 0.9303(12) 1 calc R . P A 1
H15A H -0.0236 0.7021 0.2693 0.030 Uiso 0.0697(12) 1 calc R . P A 2
C16 C 0.0491(18) 0.5236(9) 0.1461(12) 0.0370(19) Uani 0.9303(12) 1 d D U P A 1
H16A H -0.0643 0.5277 0.1378 0.056 Uiso 0.9303(12) 1 calc GR . P A 1
H16B H 0.0778 0.4565 0.2103 0.056 Uiso 0.9303(12) 1 calc GR . P A 1
H16C H 0.1383 0.4876 0.0686 0.056 Uiso 0.9303(12) 1 calc GR . P A 1
Br1A Br 0.055(2) 0.4910(16) 0.1534(17) 0.042(2) Uani 0.0697(12) 1 d D U P A 2
C16A C -0.084(8) 0.800(2) 0.119(6) 0.076(14) Uani 0.0697(12) 1 d D U P A 2
H16D H -0.0261 0.8686 0.0761 0.114 Uiso 0.0697(12) 1 d R . P A 2
H16E H -0.1907 0.8549 0.1803 0.114 Uiso 0.0697(12) 1 d R . P A 2
H16F H -0.1136 0.7493 0.0595 0.114 Uiso 0.0697(12) 1 d R . P A 2


_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 C15 1.961(2) . ?
S1 O1 1.4280(15) . ?
S1 O2 1.4252(17) . ?
S1 N1 1.675(2) . ?
S1 C1 1.754(2) . ?
O3 C7 1.213(3) . ?
N1 C7 1.386(2) . ?
N1 C8 1.490(2) . ?
C1 C2 1.379(3) . ?
C1 C6 1.383(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C6 C7 1.486(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.524(3) . ?
C8 C15 1.534(3) . ?
C9 C10 1.392(3) . ?
C9 C14 1.390(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.393(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9800 . ?
C15 H15A 0.9800 . ?
C15 C16 1.548(8) . ?
C15 Br1A 1.811(15) . ?
C15 C16A 1.537(10) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 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
O1 S1 N1 109.77(9) . . ?
O1 S1 C1 111.50(9) . . ?
O2 S1 O1 117.57(10) . . ?
O2 S1 N1 109.80(9) . . ?
O2 S1 C1 112.59(10) . . ?
N1 S1 C1 92.84(9) . . ?
C7 N1 S1 114.94(13) . . ?
C7 N1 C8 125.93(16) . . ?
C8 N1 S1 119.13(13) . . ?
C2 C1 S1 126.94(17) . . ?
C2 C1 C6 123.2(2) . . ?
C6 C1 S1 109.88(15) . . ?
C1 C2 H2 121.9 . . ?
C1 C2 C3 116.3(2) . . ?
C3 C2 H2 121.9 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.2(2) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 119.9(2) . . ?
C1 C6 C7 113.36(18) . . ?
C5 C6 C7 126.72(19) . . ?
O3 C7 N1 124.41(18) . . ?
O3 C7 C6 126.63(18) . . ?
N1 C7 C6 108.94(16) . . ?
N1 C8 H8 106.8 . . ?
N1 C8 C9 110.13(15) . . ?
N1 C8 C15 109.33(16) . . ?
C9 C8 H8 106.8 . . ?
C9 C8 C15 116.58(17) . . ?
C15 C8 H8 106.8 . . ?
C10 C9 C8 118.36(18) . . ?
C14 C9 C8 122.24(18) . . ?
C14 C9 C10 119.38(19) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.9(2) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 C13 120.2(2) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
Br1 C15 H15 109.2 . . ?
C8 C15 Br1 107.18(14) . . ?
C8 C15 H15 109.2 . . ?
C8 C15 H15A 102.2 . . ?
C8 C15 C16 113.4(5) . . ?
C8 C15 Br1A 111.2(6) . . ?
C8 C15 C16A 122(2) . . ?
C16 C15 Br1 108.6(5) . . ?
C16 C15 H15 109.2 . . ?
Br1A C15 H15A 102.2 . . ?
C16A C15 H15A 102.2 . . ?
C16A C15 Br1A 113.6(11) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C16A H16D 109.2 . . ?
C15 C16A H16E 110.0 . . ?
C15 C16A H16F 109.3 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 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
S1 N1 C7 O3 -179.02(15) . . . . ?
S1 N1 C7 C6 -0.33(19) . . . . ?
S1 N1 C8 C9 -108.17(16) . . . . ?
S1 N1 C8 C15 122.52(15) . . . . ?
S1 C1 C2 C3 -179.40(18) . . . . ?
S1 C1 C6 C5 -179.69(15) . . . . ?
S1 C1 C6 C7 2.0(2) . . . . ?
O1 S1 N1 C7 115.33(14) . . . . ?
O1 S1 N1 C8 -65.28(15) . . . . ?
O1 S1 C1 C2 65.0(2) . . . . ?
O1 S1 C1 C6 -114.43(15) . . . . ?
O2 S1 N1 C7 -113.97(14) . . . . ?
O2 S1 N1 C8 65.41(15) . . . . ?
O2 S1 C1 C2 -69.7(2) . . . . ?
O2 S1 C1 C6 110.95(15) . . . . ?
N1 S1 C1 C2 177.5(2) . . . . ?
N1 S1 C1 C6 -1.88(15) . . . . ?
N1 C8 C9 C10 91.3(2) . . . . ?
N1 C8 C9 C14 -87.1(2) . . . . ?
N1 C8 C15 Br1 -173.80(11) . . . . ?
N1 C8 C15 C16 -53.9(6) . . . . ?
N1 C8 C15 Br1A -48.8(6) . . . . ?
N1 C8 C15 C16A 173(3) . . . . ?
C1 S1 N1 C7 1.27(15) . . . . ?
C1 S1 N1 C8 -179.34(14) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C1 C6 C7 O3 177.50(19) . . . . ?
C1 C6 C7 N1 -1.1(2) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C2 C1 C6 C7 -177.4(2) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 177.4(2) . . . . ?
C5 C6 C7 O3 -0.6(3) . . . . ?
C5 C6 C7 N1 -179.29(18) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C7 N1 C8 C9 71.1(2) . . . . ?
C7 N1 C8 C15 -58.2(2) . . . . ?
C8 N1 C7 O3 1.6(3) . . . . ?
C8 N1 C7 C6 -179.67(16) . . . . ?
C8 C9 C10 C11 -177.8(2) . . . . ?
C8 C9 C14 C13 177.97(19) . . . . ?
C9 C8 C15 Br1 60.52(19) . . . . ?
C9 C8 C15 C16 -179.6(5) . . . . ?
C9 C8 C15 Br1A -174.4(6) . . . . ?
C9 C8 C15 C16A 47(3) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C10 C9 C14 C13 -0.4(3) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C9 -0.1(3) . . . . ?
C14 C9 C10 C11 0.6(3) . . . . ?
C15 C8 C9 C10 -143.43(19) . . . . ?
C15 C8 C9 C14 38.2(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1442748'
_audit_update_record             
;
2015-12-16 deposited with the CCDC.
2016-01-25 downloaded from the CCDC.
;
_audit_creation_date             2014-08-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H14 Br N O3 S'
_chemical_formula_sum            'C16 H14 Br N O3 S'
_chemical_formula_weight         380.25
_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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.825(4)
_cell_length_b                   8.982(3)
_cell_length_c                   11.426(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.905(4)
_cell_angle_gamma                90
_cell_volume                     1527.2(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4283
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4811
_cell_measurement_theta_min      2.6488
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.840
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10011
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.437
_diffrn_reflns_theta_min         1.369
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             3694
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0885
_diffrn_orient_matrix_UB_12      -0.0209
_diffrn_orient_matrix_UB_13      -0.0197
_diffrn_orient_matrix_UB_21      0.0342
_diffrn_orient_matrix_UB_22      -0.0692
_diffrn_orient_matrix_UB_23      -0.0802
_diffrn_orient_matrix_UB_31      -0.0199
_diffrn_orient_matrix_UB_32      -0.0526
_diffrn_orient_matrix_UB_33      0.0369
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3090
_reflns_number_total             3465
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.867
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3465
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0663
_refine_ls_restrained_S_all      1.126
_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)+(0.0378P)²+6.1349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1474
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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 0.43504(3) 0.73021(6) 0.49945(5) 0.04400(18) Uani 1 1 d . . . . .
S1 S 0.15348(8) 0.77270(13) 0.12858(13) 0.0373(3) Uani 1 1 d . . . . .
O1 O 0.1989(3) 0.7244(4) 0.0477(4) 0.0507(10) Uani 1 1 d . . . . .
O2 O 0.1689(2) 0.9221(4) 0.1730(4) 0.0494(10) Uani 1 1 d . . . . .
O3 O 0.1020(3) 0.4903(4) 0.3354(4) 0.0494(9) Uani 1 1 d . . . . .
N1 N 0.1749(3) 0.6547(5) 0.2489(4) 0.0384(9) Uani 1 1 d . . . . .
C1 C 0.0385(3) 0.7307(5) 0.0723(5) 0.0335(10) Uani 1 1 d . . . . .
C2 C -0.0267(4) 0.7902(6) -0.0301(5) 0.0416(11) Uani 1 1 d . . . . .
H2 H -0.0131 0.8620 -0.0795 0.050 Uiso 1 1 calc R . . . .
C3 C -0.1137(3) 0.7377(6) -0.0559(5) 0.0462(13) Uani 1 1 d . . . . .
H3 H -0.1594 0.7746 -0.1247 0.055 Uiso 1 1 calc R . . . .
C4 C -0.1336(3) 0.6337(6) 0.0170(6) 0.0499(14) Uani 1 1 d . . . . .
H4 H -0.1925 0.6003 -0.0033 0.060 Uiso 1 1 calc R . . . .
C5 C -0.0671(3) 0.5760(6) 0.1219(5) 0.0427(12) Uani 1 1 d . . . . .
H5 H -0.0812 0.5060 0.1724 0.051 Uiso 1 1 calc R . . . .
C6 C 0.0198(3) 0.6254(5) 0.1487(4) 0.0343(10) Uani 1 1 d . . . . .
C7 C 0.0996(3) 0.5794(5) 0.2545(5) 0.0378(10) Uani 1 1 d . . . . .
C8 C 0.2646(3) 0.6218(6) 0.3422(5) 0.0446(12) Uani 1 1 d . . . . .
H8 H 0.2549 0.5984 0.4205 0.054 Uiso 1 1 calc R . . . .
C9 C 0.3208(4) 0.7583(6) 0.3646(6) 0.0497(14) Uani 1 1 d . . . . .
H9A H 0.2883 0.8400 0.3853 0.060 Uiso 1 1 calc R . . . .
H9B H 0.3323 0.7846 0.2890 0.060 Uiso 1 1 calc R . . . .
C10 C 0.3048(3) 0.4835(5) 0.3049(5) 0.0389(11) Uani 1 1 d . . . . .
C11 C 0.3477(3) 0.4818(6) 0.2173(5) 0.0462(13) Uani 1 1 d . . . . .
H11 H 0.3547 0.5700 0.1791 0.055 Uiso 1 1 calc R . . . .
C12 C 0.3804(3) 0.3491(6) 0.1862(5) 0.0438(12) Uani 1 1 d . . . . .
H12 H 0.4095 0.3501 0.1278 0.053 Uiso 1 1 calc R . . . .
C13 C 0.3703(3) 0.2153(6) 0.2408(5) 0.0367(10) Uani 1 1 d . . . . .
C14 C 0.3283(3) 0.2196(6) 0.3285(5) 0.0374(10) Uani 1 1 d . . . . .
H14 H 0.3215 0.1316 0.3673 0.045 Uiso 1 1 calc R . . . .
C15 C 0.2962(3) 0.3502(6) 0.3604(5) 0.0400(11) Uani 1 1 d . . . . .
H15 H 0.2683 0.3489 0.4202 0.048 Uiso 1 1 calc R . . . .
C16 C 0.4027(4) 0.0711(6) 0.2063(6) 0.0510(14) Uani 1 1 d . . . . .
H16A H 0.3523 0.0138 0.1560 0.077 Uiso 1 1 calc GR . . . .
H16B H 0.4344 0.0165 0.2805 0.077 Uiso 1 1 calc GR . . . .
H16C H 0.4423 0.0905 0.1604 0.077 Uiso 1 1 calc GR . . . .


_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 1.952(6) . ?
S1 O1 1.419(4) . ?
S1 O2 1.427(4) . ?
S1 N1 1.676(4) . ?
S1 C1 1.752(5) . ?
O3 C7 1.213(6) . ?
N1 C7 1.392(6) . ?
N1 C8 1.486(6) . ?
C1 C2 1.377(7) . ?
C1 C6 1.386(7) . ?
C2 C3 1.389(8) . ?
C3 C4 1.357(8) . ?
C4 C5 1.399(8) . ?
C5 C6 1.377(6) . ?
C6 C7 1.478(6) . ?
C8 C9 1.485(7) . ?
C8 C10 1.522(7) . ?
C10 C11 1.387(8) . ?
C10 C15 1.383(7) . ?
C11 C12 1.393(8) . ?
C12 C13 1.388(7) . ?
C13 C14 1.379(7) . ?
C13 C16 1.494(7) . ?
C14 C15 1.376(7) . ?

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
O1 S1 O2 117.1(3) . . ?
O1 S1 N1 109.6(2) . . ?
O1 S1 C1 112.9(2) . . ?
O2 S1 N1 109.9(2) . . ?
O2 S1 C1 111.4(2) . . ?
N1 S1 C1 93.4(2) . . ?
C7 N1 S1 114.1(3) . . ?
C7 N1 C8 119.6(4) . . ?
C8 N1 S1 126.3(4) . . ?
C2 C1 S1 127.7(4) . . ?
C2 C1 C6 122.8(5) . . ?
C6 C1 S1 109.5(3) . . ?
C1 C2 C3 116.8(5) . . ?
C4 C3 C2 121.6(5) . . ?
C3 C4 C5 121.1(5) . . ?
C6 C5 C4 118.3(5) . . ?
C1 C6 C7 113.6(4) . . ?
C5 C6 C1 119.4(5) . . ?
C5 C6 C7 127.0(5) . . ?
O3 C7 N1 123.4(5) . . ?
O3 C7 C6 127.2(5) . . ?
N1 C7 C6 109.4(4) . . ?
N1 C8 C10 110.5(4) . . ?
C9 C8 N1 109.2(4) . . ?
C9 C8 C10 116.0(5) . . ?
C8 C9 Br1 111.6(4) . . ?
C11 C10 C8 124.4(5) . . ?
C15 C10 C8 117.5(5) . . ?
C15 C10 C11 118.1(5) . . ?
C10 C11 C12 120.6(5) . . ?
C13 C12 C11 121.1(5) . . ?
C12 C13 C16 122.0(5) . . ?
C14 C13 C12 117.4(5) . . ?
C14 C13 C16 120.6(5) . . ?
C15 C14 C13 121.9(5) . . ?
C14 C15 C10 120.9(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
S1 N1 C7 O3 -179.6(4) . . . . ?
S1 N1 C7 C6 0.6(5) . . . . ?
S1 N1 C8 C9 33.7(7) . . . . ?
S1 N1 C8 C10 -95.0(5) . . . . ?
S1 C1 C2 C3 179.8(4) . . . . ?
S1 C1 C6 C5 179.8(4) . . . . ?
S1 C1 C6 C7 0.5(5) . . . . ?
O1 S1 N1 C7 -116.0(4) . . . . ?
O1 S1 N1 C8 61.4(5) . . . . ?
O1 S1 C1 C2 -68.0(5) . . . . ?
O1 S1 C1 C6 112.8(4) . . . . ?
O2 S1 N1 C7 113.9(4) . . . . ?
O2 S1 N1 C8 -68.7(5) . . . . ?
O2 S1 C1 C2 66.2(5) . . . . ?
O2 S1 C1 C6 -113.1(4) . . . . ?
N1 S1 C1 C2 179.1(5) . . . . ?
N1 S1 C1 C6 -0.1(4) . . . . ?
N1 C8 C9 Br1 173.7(4) . . . . ?
N1 C8 C10 C11 80.2(6) . . . . ?
N1 C8 C10 C15 -98.4(5) . . . . ?
C1 S1 N1 C7 -0.3(4) . . . . ?
C1 S1 N1 C8 177.1(4) . . . . ?
C1 C2 C3 C4 0.6(8) . . . . ?
C1 C6 C7 O3 179.5(5) . . . . ?
C1 C6 C7 N1 -0.7(6) . . . . ?
C2 C1 C6 C5 0.6(7) . . . . ?
C2 C1 C6 C7 -178.8(4) . . . . ?
C2 C3 C4 C5 0.5(8) . . . . ?
C3 C4 C5 C6 -1.1(8) . . . . ?
C4 C5 C6 C1 0.6(8) . . . . ?
C4 C5 C6 C7 179.8(5) . . . . ?
C5 C6 C7 O3 0.2(9) . . . . ?
C5 C6 C7 N1 -180.0(5) . . . . ?
C6 C1 C2 C3 -1.1(7) . . . . ?
C7 N1 C8 C9 -149.0(5) . . . . ?
C7 N1 C8 C10 82.2(6) . . . . ?
C8 N1 C7 O3 2.8(8) . . . . ?
C8 N1 C7 C6 -177.0(4) . . . . ?
C8 C10 C11 C12 -178.2(4) . . . . ?
C8 C10 C15 C14 177.9(4) . . . . ?
C9 C8 C10 C11 -44.7(7) . . . . ?
C9 C8 C10 C15 136.7(5) . . . . ?
C10 C8 C9 Br1 -60.6(6) . . . . ?
C10 C11 C12 C13 0.6(8) . . . . ?
C11 C10 C15 C14 -0.8(7) . . . . ?
C11 C12 C13 C14 -1.2(7) . . . . ?
C11 C12 C13 C16 178.4(5) . . . . ?
C12 C13 C14 C15 0.8(7) . . . . ?
C13 C14 C15 C10 0.2(8) . . . . ?
C15 C10 C11 C12 0.4(7) . . . . ?
C16 C13 C14 C15 -178.7(5) . . . . ?

