# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_sa3368
_audit_block_doi                 10.5517/cc13vfx9
_database_code_depnum_ccdc_archive 'CCDC 1038311'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;
_audit_creation_date             2014-05-12
_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         'C14 H16 Br N O4 S'
_chemical_formula_sum            'C14 H16 Br N O4 S'
_chemical_formula_weight         374.25
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.0644(6)
_cell_length_b                   11.5331(10)
_cell_length_c                   8.2552(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.154(5)
_cell_angle_gamma                90
_cell_volume                     764.69(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2821
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4713
_cell_measurement_theta_min      2.5359
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.838
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.29
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8525
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_min         3.043
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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             1851
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0079
_diffrn_orient_matrix_UB_12      -0.1240
_diffrn_orient_matrix_UB_13      0.0072
_diffrn_orient_matrix_UB_21      -0.0180
_diffrn_orient_matrix_UB_22      0.0060
_diffrn_orient_matrix_UB_23      0.0846
_diffrn_orient_matrix_UB_31      -0.1189
_diffrn_orient_matrix_UB_32      -0.0049
_diffrn_orient_matrix_UB_33      -0.0250
_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         0.782
_reflns_Friedel_fraction_full    0.888
_reflns_Friedel_fraction_max     0.862
_reflns_number_gt                3249
_reflns_number_total             3285
_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         0.263
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 
;
 Flack x determined using 1392 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.007(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3285
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.166
_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)+(0.0330P)²+0.1197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0659
_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), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_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 0.30967(4) 0.66331(3) 0.66584(4) 0.03125(11) Uani 1 1 d . . . . .
S1 S 0.50062(9) 0.70150(6) 0.18657(9) 0.01695(16) Uani 1 1 d . . . . .
O1 O 0.6645(3) 0.5515(2) 0.5893(3) 0.0250(5) Uani 1 1 d . . . . .
O2 O 0.6194(3) 0.49105(19) 0.3371(3) 0.0215(5) Uani 1 1 d . . . . .
O3 O 0.6315(2) 0.6669(3) 0.0905(2) 0.0248(5) Uani 1 1 d . . . . .
O4 O 0.4440(3) 0.8191(2) 0.1791(3) 0.0251(5) Uani 1 1 d . . . . .
N1 N 0.5653(3) 0.6809(2) 0.3853(3) 0.0157(5) Uani 1 1 d . . . . .
C1 C 0.5580(4) 0.7799(3) 0.4991(4) 0.0180(6) Uani 1 1 d . . . . .
H1 H 0.4614 0.8279 0.4631 0.022 Uiso 1 1 calc R . . . .
C2 C 0.5330(4) 0.7309(3) 0.6664(4) 0.0224(6) Uani 1 1 d . . . . .
H2 H 0.5442 0.7938 0.7464 0.027 Uiso 1 1 calc R . . . .
C3 C 0.6623(5) 0.6404(3) 0.7126(4) 0.0286(8) Uani 1 1 d . . . . .
H3A H 0.7710 0.6768 0.7279 0.034 Uiso 1 1 calc R . . . .
H3B H 0.6394 0.6051 0.8149 0.034 Uiso 1 1 calc R . . . .
C4 C 0.6176(4) 0.5709(3) 0.4318(4) 0.0174(6) Uani 1 1 d . . . . .
C5 C 0.7119(4) 0.8545(3) 0.5061(4) 0.0220(7) Uani 1 1 d . . . . .
H5 H 0.7129 0.9199 0.5721 0.026 Uiso 1 1 calc R . . . .
C6 C 0.8457(4) 0.8363(3) 0.4278(5) 0.0267(7) Uani 1 1 d . . . . .
H6 H 0.8479 0.7696 0.3647 0.032 Uiso 1 1 calc R . . . .
C7 C 0.9937(5) 0.9148(4) 0.4329(6) 0.0362(9) Uani 1 1 d . . . . .
H7A H 1.0090 0.9411 0.3249 0.054 Uiso 1 1 calc GR . . . .
H7B H 1.0911 0.8733 0.4761 0.054 Uiso 1 1 calc GR . . . .
H7C H 0.9762 0.9803 0.5010 0.054 Uiso 1 1 calc GR . . . .
C8 C 0.3291(4) 0.6088(3) 0.1487(4) 0.0171(6) Uani 1 1 d . . . . .
C9 C 0.3435(4) 0.5061(3) 0.0628(4) 0.0204(6) Uani 1 1 d . . . . .
H9 H 0.4447 0.4846 0.0261 0.024 Uiso 1 1 calc R . . . .
C10 C 0.2041(4) 0.4365(3) 0.0332(4) 0.0236(7) Uani 1 1 d . . . . .
H10 H 0.2125 0.3676 -0.0240 0.028 Uiso 1 1 calc R . . . .
C11 C 0.0512(4) 0.4678(3) 0.0874(4) 0.0232(7) Uani 1 1 d . . . . .
C12 C 0.0404(4) 0.5718(3) 0.1718(4) 0.0246(7) Uani 1 1 d . . . . .
H12 H -0.0611 0.5941 0.2072 0.029 Uiso 1 1 calc R . . . .
C13 C 0.1781(4) 0.6426(3) 0.2041(4) 0.0207(7) Uani 1 1 d . . . . .
H13 H 0.1701 0.7114 0.2616 0.025 Uiso 1 1 calc R . . . .
C14 C -0.1007(5) 0.3923(4) 0.0554(6) 0.0391(10) Uani 1 1 d . . . . .
H14A H -0.1479 0.4037 -0.0543 0.059 Uiso 1 1 calc GR . . . .
H14B H -0.1812 0.4125 0.1295 0.059 Uiso 1 1 calc GR . . . .
H14C H -0.0696 0.3124 0.0708 0.059 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 C2 1.962(3) . ?
S1 O3 1.433(2) . ?
S1 O4 1.431(3) . ?
S1 N1 1.693(3) . ?
S1 C8 1.754(3) . ?
O1 C3 1.446(4) . ?
O1 C4 1.340(4) . ?
O2 C4 1.209(4) . ?
N1 C1 1.483(4) . ?
N1 C4 1.380(4) . ?
C1 C2 1.522(5) . ?
C1 C5 1.506(4) . ?
C2 C3 1.500(5) . ?
C5 C6 1.324(5) . ?
C6 C7 1.495(5) . ?
C8 C9 1.390(5) . ?
C8 C13 1.394(4) . ?
C9 C10 1.385(5) . ?
C10 C11 1.397(5) . ?
C11 C12 1.394(5) . ?
C11 C14 1.507(5) . ?
C12 C13 1.384(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
O3 S1 N1 108.61(13) . . ?
O3 S1 C8 109.86(16) . . ?
O4 S1 O3 119.25(16) . . ?
O4 S1 N1 104.15(14) . . ?
O4 S1 C8 109.08(15) . . ?
N1 S1 C8 104.84(14) . . ?
C4 O1 C3 123.0(3) . . ?
C1 N1 S1 118.6(2) . . ?
C4 N1 S1 117.3(2) . . ?
C4 N1 C1 124.1(3) . . ?
N1 C1 C2 107.7(2) . . ?
N1 C1 C5 112.7(3) . . ?
C5 C1 C2 110.7(3) . . ?
C1 C2 Br1 110.0(2) . . ?
C3 C2 Br1 109.9(3) . . ?
C3 C2 C1 110.1(3) . . ?
O1 C3 C2 111.5(3) . . ?
O1 C4 N1 118.4(3) . . ?
O2 C4 O1 118.8(3) . . ?
O2 C4 N1 122.8(3) . . ?
C6 C5 C1 126.6(3) . . ?
C5 C6 C7 125.0(3) . . ?
C9 C8 S1 120.6(2) . . ?
C9 C8 C13 121.4(3) . . ?
C13 C8 S1 118.0(3) . . ?
C10 C9 C8 118.7(3) . . ?
C9 C10 C11 121.3(3) . . ?
C10 C11 C14 121.4(3) . . ?
C12 C11 C10 118.6(3) . . ?
C12 C11 C14 119.9(3) . . ?
C13 C12 C11 121.2(3) . . ?
C12 C13 C8 118.8(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 C2 C3 O1 67.2(3) . . . . ?
S1 N1 C1 C2 151.0(2) . . . . ?
S1 N1 C1 C5 -86.7(3) . . . . ?
S1 N1 C4 O1 -178.0(2) . . . . ?
S1 N1 C4 O2 0.4(4) . . . . ?
S1 C8 C9 C10 -178.8(3) . . . . ?
S1 C8 C13 C12 178.5(2) . . . . ?
O3 S1 N1 C1 125.7(2) . . . . ?
O3 S1 N1 C4 -56.0(3) . . . . ?
O3 S1 C8 C9 11.8(3) . . . . ?
O3 S1 C8 C13 -166.8(3) . . . . ?
O4 S1 N1 C1 -2.4(3) . . . . ?
O4 S1 N1 C4 175.9(2) . . . . ?
O4 S1 C8 C9 144.2(3) . . . . ?
O4 S1 C8 C13 -34.4(3) . . . . ?
N1 S1 C8 C9 -104.7(3) . . . . ?
N1 S1 C8 C13 76.7(3) . . . . ?
N1 C1 C2 Br1 -68.8(3) . . . . ?
N1 C1 C2 C3 52.4(3) . . . . ?
N1 C1 C5 C6 -2.5(5) . . . . ?
C1 N1 C4 O1 0.2(4) . . . . ?
C1 N1 C4 O2 178.6(3) . . . . ?
C1 C2 C3 O1 -54.1(4) . . . . ?
C1 C5 C6 C7 177.6(4) . . . . ?
C2 C1 C5 C6 118.1(4) . . . . ?
C3 O1 C4 O2 -178.2(3) . . . . ?
C3 O1 C4 N1 0.2(5) . . . . ?
C4 O1 C3 C2 27.6(5) . . . . ?
C4 N1 C1 C2 -27.2(4) . . . . ?
C4 N1 C1 C5 95.1(3) . . . . ?
C5 C1 C2 Br1 167.6(2) . . . . ?
C5 C1 C2 C3 -71.1(4) . . . . ?
C8 S1 N1 C1 -117.0(2) . . . . ?
C8 S1 N1 C4 61.4(2) . . . . ?
C8 C9 C10 C11 0.1(5) . . . . ?
C9 C8 C13 C12 -0.1(5) . . . . ?
C9 C10 C11 C12 0.5(5) . . . . ?
C9 C10 C11 C14 -180.0(4) . . . . ?
C10 C11 C12 C13 -0.9(5) . . . . ?
C11 C12 C13 C8 0.8(5) . . . . ?
C13 C8 C9 C10 -0.3(5) . . . . ?
C14 C11 C12 C13 179.5(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_sa3653
_audit_block_doi                 10.5517/cc13vfyb
_database_code_depnum_ccdc_archive 'CCDC 1038312'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;
_audit_creation_date             2014-10-10
_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         'C14 H15 Br N4 O4 S'
_chemical_formula_sum            'C14 H15 Br N4 O4 S'
_chemical_formula_weight         415.27
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.079(2)
_cell_length_b                   11.113(3)
_cell_length_c                   18.417(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1653.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5587
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4699
_cell_measurement_theta_min      2.1405
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18210
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         3.117
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_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             2185
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0132
_diffrn_orient_matrix_UB_12      0.0239
_diffrn_orient_matrix_UB_13      -0.1207
_diffrn_orient_matrix_UB_21      -0.0155
_diffrn_orient_matrix_UB_22      0.0866
_diffrn_orient_matrix_UB_23      0.0188
_diffrn_orient_matrix_UB_31      0.0532
_diffrn_orient_matrix_UB_32      0.0103
_diffrn_orient_matrix_UB_33      -0.0038
_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         0.742
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3714
_reflns_number_total             3757
_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         0.316
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1539 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.011(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0235
_refine_ls_restrained_S_all      1.091
_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)+(0.0271P)²+0.3870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0567
_refine_ls_wR_factor_ref         0.0569
_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), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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 0.67493(3) 0.75423(3) 0.17062(2) 0.02948(9) Uani 1 1 d . . . . .
S1 S 0.17234(8) 0.69456(5) 0.24191(4) 0.02052(13) Uani 1 1 d . . . . .
O1 O 0.5422(2) 0.87169(16) 0.32381(11) 0.0243(4) Uani 1 1 d . . . . .
O2 O 0.2878(2) 0.92181(16) 0.29534(11) 0.0255(4) Uani 1 1 d . . . . .
O3 O 0.1863(2) 0.57200(16) 0.21990(12) 0.0281(4) Uani 1 1 d . . . . .
O4 O 0.0491(2) 0.72745(19) 0.29353(11) 0.0282(4) Uani 1 1 d . . . . .
N1 N 0.3617(2) 0.72608(17) 0.27716(12) 0.0174(4) Uani 1 1 d . . . . .
N2 N 0.3816(4) 0.5629(3) 0.53651(17) 0.0493(8) Uani 1 1 d . . . . .
N3 N 0.4838(4) 0.6444(3) 0.53582(15) 0.0454(7) Uani 1 1 d . . . . .
N4 N 0.5727(6) 0.7226(3) 0.5402(2) 0.0703(12) Uani 1 1 d . . . . .
C1 C 0.6575(3) 0.6896(2) 0.26930(14) 0.0204(5) Uani 1 1 d . . . . .
H1 H 0.7439 0.6288 0.2765 0.024 Uiso 1 1 calc R . . . .
C2 C 0.4886(3) 0.6309(2) 0.27892(14) 0.0187(5) Uani 1 1 d . . . . .
H2 H 0.4693 0.5760 0.2381 0.022 Uiso 1 1 calc R . . . .
C3 C 0.3909(3) 0.8440(2) 0.29891(14) 0.0188(5) Uani 1 1 d . . . . .
C4 C 0.6803(3) 0.7883(2) 0.32400(15) 0.0227(5) Uani 1 1 d . . . . .
H4A H 0.6914 0.7532 0.3720 0.027 Uiso 1 1 calc R . . . .
H4B H 0.7815 0.8317 0.3132 0.027 Uiso 1 1 calc R . . . .
C5 C 0.4844(3) 0.5594(2) 0.34834(15) 0.0219(5) Uani 1 1 d . . . . .
H5 H 0.5653 0.5007 0.3544 0.026 Uiso 1 1 calc R . . . .
C6 C 0.3767(3) 0.5727(2) 0.40117(16) 0.0245(6) Uani 1 1 d . . . . .
H6 H 0.2988 0.6340 0.3972 0.029 Uiso 1 1 calc R . . . .
C7 C 0.3723(4) 0.4947(3) 0.46743(17) 0.0328(7) Uani 1 1 d . . . . .
H7A H 0.2708 0.4481 0.4670 0.039 Uiso 1 1 calc R . . . .
H7B H 0.4642 0.4386 0.4654 0.039 Uiso 1 1 calc R . . . .
C8 C 0.1563(3) 0.7858(2) 0.16430(14) 0.0209(5) Uani 1 1 d . . . . .
C9 C 0.2246(3) 0.7446(3) 0.09992(15) 0.0280(5) Uani 1 1 d . . . . .
H9 H 0.2781 0.6705 0.0981 0.034 Uiso 1 1 calc R . . . .
C10 C 0.2117(4) 0.8154(3) 0.03817(17) 0.0333(7) Uani 1 1 d . . . . .
H10 H 0.2580 0.7887 -0.0052 0.040 Uiso 1 1 calc R . . . .
C11 C 0.1306(4) 0.9259(3) 0.04000(17) 0.0302(6) Uani 1 1 d . . . . .
C12 C 0.0630(3) 0.9647(3) 0.10548(17) 0.0268(6) Uani 1 1 d . . . . .
H12 H 0.0089 1.0385 0.1073 0.032 Uiso 1 1 calc R . . . .
C13 C 0.0745(3) 0.8960(2) 0.16792(16) 0.0226(5) Uani 1 1 d . . . . .
H13 H 0.0286 0.9228 0.2113 0.027 Uiso 1 1 calc R . . . .
C14 C 0.1142(6) 1.0014(4) -0.0278(2) 0.0468(9) Uani 1 1 d . . . . .
H14A H 0.1992 0.9793 -0.0617 0.070 Uiso 1 1 calc GR . . . .
H14B H 0.1254 1.0849 -0.0155 0.070 Uiso 1 1 calc GR . . . .
H14C H 0.0076 0.9879 -0.0493 0.070 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 C1 1.959(3) . ?
S1 O3 1.4255(19) . ?
S1 O4 1.424(2) . ?
S1 N1 1.698(2) . ?
S1 C8 1.757(3) . ?
O1 C3 1.341(3) . ?
O1 C4 1.450(3) . ?
O2 C3 1.202(3) . ?
N1 C2 1.474(3) . ?
N1 C3 1.391(3) . ?
N2 N3 1.226(5) . ?
N2 C7 1.483(5) . ?
N3 N4 1.130(5) . ?
C1 C2 1.524(3) . ?
C1 C4 1.500(4) . ?
C2 C5 1.505(4) . ?
C5 C6 1.314(4) . ?
C6 C7 1.497(4) . ?
C8 C9 1.386(4) . ?
C8 C13 1.393(3) . ?
C9 C10 1.387(4) . ?
C10 C11 1.392(4) . ?
C11 C12 1.392(4) . ?
C11 C14 1.510(4) . ?
C12 C13 1.383(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
O3 S1 N1 103.57(11) . . ?
O3 S1 C8 109.03(12) . . ?
O4 S1 O3 119.35(13) . . ?
O4 S1 N1 108.76(12) . . ?
O4 S1 C8 110.07(12) . . ?
N1 S1 C8 104.97(11) . . ?
C3 O1 C4 123.7(2) . . ?
C2 N1 S1 119.14(16) . . ?
C3 N1 S1 117.23(16) . . ?
C3 N1 C2 123.5(2) . . ?
N3 N2 C7 113.8(3) . . ?
N4 N3 N2 174.5(4) . . ?
C2 C1 Br1 109.22(17) . . ?
C4 C1 Br1 110.25(18) . . ?
C4 C1 C2 110.2(2) . . ?
N1 C2 C1 108.25(19) . . ?
N1 C2 C5 112.5(2) . . ?
C5 C2 C1 110.2(2) . . ?
O1 C3 N1 118.0(2) . . ?
O2 C3 O1 119.1(2) . . ?
O2 C3 N1 123.0(2) . . ?
O1 C4 C1 111.8(2) . . ?
C6 C5 C2 125.8(2) . . ?
C5 C6 C7 123.7(3) . . ?
N2 C7 C6 113.7(3) . . ?
C9 C8 S1 118.4(2) . . ?
C9 C8 C13 121.4(3) . . ?
C13 C8 S1 120.2(2) . . ?
C8 C9 C10 118.9(3) . . ?
C9 C10 C11 121.1(3) . . ?
C10 C11 C12 118.6(3) . . ?
C10 C11 C14 120.7(3) . . ?
C12 C11 C14 120.6(3) . . ?
C13 C12 C11 121.5(3) . . ?
C12 C13 C8 118.5(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 C1 C2 N1 -67.9(2) . . . . ?
Br1 C1 C2 C5 168.74(17) . . . . ?
Br1 C1 C4 O1 69.2(2) . . . . ?
S1 N1 C2 C1 147.37(18) . . . . ?
S1 N1 C2 C5 -90.7(2) . . . . ?
S1 N1 C3 O1 -177.05(18) . . . . ?
S1 N1 C3 O2 1.9(4) . . . . ?
S1 C8 C9 C10 179.6(2) . . . . ?
S1 C8 C13 C12 -179.4(2) . . . . ?
O3 S1 N1 C2 -0.8(2) . . . . ?
O3 S1 N1 C3 175.40(19) . . . . ?
O3 S1 C8 C9 -26.2(2) . . . . ?
O3 S1 C8 C13 152.8(2) . . . . ?
O4 S1 N1 C2 127.13(19) . . . . ?
O4 S1 N1 C3 -56.7(2) . . . . ?
O4 S1 C8 C9 -158.9(2) . . . . ?
O4 S1 C8 C13 20.1(2) . . . . ?
N1 S1 C8 C9 84.2(2) . . . . ?
N1 S1 C8 C13 -96.7(2) . . . . ?
N1 C2 C5 C6 3.6(4) . . . . ?
N3 N2 C7 C6 -42.9(4) . . . . ?
C1 C2 C5 C6 124.4(3) . . . . ?
C2 N1 C3 O1 -1.1(4) . . . . ?
C2 N1 C3 O2 177.9(2) . . . . ?
C2 C1 C4 O1 -51.5(3) . . . . ?
C2 C5 C6 C7 176.5(3) . . . . ?
C3 O1 C4 C1 22.2(3) . . . . ?
C3 N1 C2 C1 -28.6(3) . . . . ?
C3 N1 C2 C5 93.4(3) . . . . ?
C4 O1 C3 O2 -173.9(2) . . . . ?
C4 O1 C3 N1 5.1(4) . . . . ?
C4 C1 C2 N1 53.3(3) . . . . ?
C4 C1 C2 C5 -70.0(3) . . . . ?
C5 C6 C7 N2 124.9(3) . . . . ?
C8 S1 N1 C2 -115.10(19) . . . . ?
C8 S1 N1 C3 61.1(2) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
C9 C8 C13 C12 -0.3(4) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
C9 C10 C11 C14 -178.8(3) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C11 C12 C13 C8 0.2(4) . . . . ?
C13 C8 C9 C10 0.5(4) . . . . ?
C14 C11 C12 C13 179.0(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_sa3281b
_audit_block_doi                 10.5517/cc13vfzc
_database_code_depnum_ccdc_archive 'CCDC 1038313'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;
_audit_creation_date             2014-03-24
_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         'C15 H18 Br N O4 S'
_chemical_formula_sum            'C15 H18 Br N O4 S'
_chemical_formula_weight         388.27
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.1106(16)
_cell_length_b                   15.869(3)
_cell_length_c                   13.458(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.33(3)
_cell_angle_gamma                90
_cell_volume                     1670.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5532
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4853
_cell_measurement_theta_min      1.5690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.602
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.48329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.133
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18963
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         1.569
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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             7632
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0266
_diffrn_orient_matrix_UB_12      -0.0269
_diffrn_orient_matrix_UB_13      -0.1221
_diffrn_orient_matrix_UB_21      -0.0158
_diffrn_orient_matrix_UB_22      0.0679
_diffrn_orient_matrix_UB_23      -0.0329
_diffrn_orient_matrix_UB_31      0.0609
_diffrn_orient_matrix_UB_32      0.0070
_diffrn_orient_matrix_UB_33      -0.0148
_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         0.909
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                7032
_reflns_number_total             7586
_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  'XL (Sheldrick, 2013)'
_computing_structure_solution    
;
'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Flack x determined using 2742 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.001(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         7586
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.100
_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)+(0.0359P)²+0.0091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1043
_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:
 C25(H25), C26(H26), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C21(H21), C22(H22), C27(H27), C3(H3), C4(H4), C6(H6),
 C7(H7), C12(H12)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C1(H1A,H1B,
 H1C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_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
Br2 Br 0.34493(8) 0.41304(4) 1.06480(5) 0.03756(17) Uani 1 1 d . . . . .
S2 S 0.83282(19) 0.41979(13) 0.95312(15) 0.0446(5) Uani 1 1 d . . . . .
O5 O 0.8827(6) 0.3432(3) 1.0076(5) 0.070(2) Uani 1 1 d . . . . .
O6 O 0.8857(6) 0.4369(4) 0.8629(4) 0.074(2) Uani 1 1 d . . . . .
O7 O 0.6027(6) 0.5500(3) 0.8597(3) 0.0367(11) Uani 1 1 d . . . . .
O8 O 0.3592(5) 0.4835(3) 0.8443(3) 0.0303(9) Uani 1 1 d . . . . .
N1 N 0.6171(5) 0.4165(4) 0.9231(4) 0.0279(10) Uani 1 1 d . . . . .
C16 C 1.0256(12) 0.7080(6) 1.2526(7) 0.069(3) Uani 1 1 d . . . . .
H16A H 0.9258 0.7250 1.2731 0.103 Uiso 1 1 calc GR . . . .
H16B H 1.0668 0.7546 1.2205 0.103 Uiso 1 1 calc GR . . . .
H16C H 1.1128 0.6904 1.3122 0.103 Uiso 1 1 calc GR . . . .
C17 C 0.9808(9) 0.6361(5) 1.1776(6) 0.0399(16) Uani 1 1 d . . . . .
C18 C 0.9283(8) 0.5593(5) 1.2076(5) 0.0389(16) Uani 1 1 d . . . . .
H18 H 0.9225 0.5527 1.2752 0.047 Uiso 1 1 calc R . . . .
C19 C 0.8844(7) 0.4925(5) 1.1407(5) 0.0338(13) Uani 1 1 d . . . . .
H19 H 0.8514 0.4411 1.1626 0.041 Uiso 1 1 calc R . . . .
C20 C 0.8908(7) 0.5039(4) 1.0394(5) 0.0326(14) Uani 1 1 d . . . . .
C21 C 0.9447(9) 0.5795(5) 1.0076(5) 0.0413(16) Uani 1 1 d . . . . .
H21 H 0.9508 0.5862 0.9400 0.050 Uiso 1 1 calc R . . . .
C22 C 0.9893(9) 0.6447(5) 1.0773(6) 0.0445(18) Uani 1 1 d . . . . .
H22 H 1.0259 0.6955 1.0561 0.053 Uiso 1 1 calc R . . . .
C23 C 0.5315(7) 0.4861(4) 0.8743(4) 0.0275(12) Uani 1 1 d . . . . .
C24 C 0.2674(7) 0.4056(4) 0.8447(4) 0.0314(13) Uani 1 1 d . . . . .
H24A H 0.2649 0.3738 0.7828 0.038 Uiso 1 1 calc R . . . .
H24B H 0.1504 0.4178 0.8452 0.038 Uiso 1 1 calc R . . . .
C25 C 0.3527(8) 0.3543(4) 0.9380(5) 0.0300(13) Uani 1 1 d . . . . .
H25 H 0.2909 0.3008 0.9349 0.036 Uiso 1 1 calc R . . . .
C26 C 0.5350(8) 0.3352(4) 0.9370(5) 0.0276(12) Uani 1 1 d . . . . .
H26 H 0.5956 0.3108 1.0035 0.033 Uiso 1 1 calc R . . . .
C27 C 0.5399(8) 0.2732(4) 0.8523(5) 0.0314(14) Uani 1 1 d . . . . .
H27 H 0.5515 0.2947 0.7902 0.038 Uiso 1 1 calc R . . . .
C28 C 0.5286(8) 0.1908(4) 0.8608(5) 0.0317(14) Uani 1 1 d . . . . .
C29 C 0.5150(11) 0.1467(4) 0.9561(5) 0.0436(17) Uani 1 1 d . . . . .
H29A H 0.5085 0.1877 1.0075 0.065 Uiso 1 1 calc GR . . . .
H29B H 0.6137 0.1118 0.9815 0.065 Uiso 1 1 calc GR . . . .
H29C H 0.4139 0.1124 0.9407 0.065 Uiso 1 1 calc GR . . . .
C30 C 0.5332(10) 0.1343(5) 0.7727(6) 0.0448(18) Uani 1 1 d . . . . .
H30A H 0.5441 0.1677 0.7153 0.067 Uiso 1 1 calc GR . . . .
H30B H 0.4294 0.1021 0.7530 0.067 Uiso 1 1 calc GR . . . .
H30C H 0.6290 0.0967 0.7931 0.067 Uiso 1 1 calc GR . . . .
Br1 Br 0.31752(8) 0.49536(4) 0.40298(5) 0.03840(18) Uani 1 1 d . . . . .
S1 S 0.87401(19) 0.46538(10) 0.53698(12) 0.0289(3) Uani 1 1 d . . . . .
O1 O 1.0026(5) 0.4452(3) 0.6290(3) 0.0413(12) Uani 1 1 d . . . . .
O2 O 0.8953(6) 0.5380(3) 0.4788(4) 0.0393(11) Uani 1 1 d . . . . .
O3 O 0.6943(6) 0.3518(3) 0.6355(3) 0.0341(10) Uani 1 1 d . . . . .
O4 O 0.4791(5) 0.4346(3) 0.6431(3) 0.0311(10) Uani 1 1 d . . . . .
N2 N 0.6871(6) 0.4832(3) 0.5656(4) 0.0251(10) Uani 1 1 d . . . . .
C1 C 0.8011(11) 0.1725(5) 0.2436(6) 0.0494(19) Uani 1 1 d . . . . .
H1A H 0.8448 0.1914 0.1877 0.074 Uiso 1 1 calc GR . . . .
H1B H 0.6844 0.1550 0.2172 0.074 Uiso 1 1 calc GR . . . .
H1C H 0.8683 0.1259 0.2776 0.074 Uiso 1 1 calc GR . . . .
C2 C 0.8101(8) 0.2430(4) 0.3188(5) 0.0345(15) Uani 1 1 d . . . . .
C3 C 0.9085(9) 0.2362(4) 0.4202(5) 0.0389(16) Uani 1 1 d . . . . .
H3 H 0.9648 0.1859 0.4428 0.047 Uiso 1 1 calc R . . . .
C4 C 0.9239(8) 0.3026(5) 0.4877(5) 0.0350(15) Uani 1 1 d . . . . .
H4 H 0.9907 0.2972 0.5551 0.042 Uiso 1 1 calc R . . . .
C5 C 0.8392(7) 0.3779(4) 0.4548(4) 0.0257(12) Uani 1 1 d . . . . .
C6 C 0.7375(8) 0.3861(4) 0.3546(5) 0.0337(14) Uani 1 1 d . . . . .
H6 H 0.6799 0.4361 0.3325 0.040 Uiso 1 1 calc R . . . .
C7 C 0.7234(9) 0.3186(4) 0.2886(5) 0.0379(16) Uani 1 1 d . . . . .
H7 H 0.6540 0.3235 0.2218 0.045 Uiso 1 1 calc R . . . .
C8 C 0.6252(7) 0.4191(4) 0.6165(4) 0.0271(12) Uani 1 1 d . . . . .
C9 C 0.3874(8) 0.5133(4) 0.6209(5) 0.0336(15) Uani 1 1 d . . . . .
H9A H 0.4219 0.5498 0.6806 0.040 Uiso 1 1 calc R . . . .
H9B H 0.2660 0.5024 0.6086 0.040 Uiso 1 1 calc R . . . .
C10 C 0.4180(8) 0.5580(4) 0.5292(5) 0.0300(13) Uani 1 1 d . . . . .
H10 H 0.3650 0.6139 0.5239 0.036 Uiso 1 1 calc R . . . .
C11 C 0.6106(8) 0.5684(4) 0.5472(4) 0.0262(12) Uani 1 1 d . . . . .
H11 H 0.6337 0.5920 0.4850 0.031 Uiso 1 1 calc R . . . .
C12 C 0.6837(8) 0.6264(4) 0.6368(5) 0.0295(13) Uani 1 1 d . . . . .
H12 H 0.7300 0.6019 0.7008 0.035 Uiso 1 1 calc R . . . .
C13 C 0.6868(9) 0.7085(4) 0.6311(5) 0.0357(15) Uani 1 1 d . . . . .
C14 C 0.7553(10) 0.7620(5) 0.7253(6) 0.054(2) Uani 1 1 d . . . . .
H14A H 0.7882 0.7264 0.7850 0.081 Uiso 1 1 calc GR . . . .
H14B H 0.6684 0.8005 0.7331 0.081 Uiso 1 1 calc GR . . . .
H14C H 0.8530 0.7930 0.7180 0.081 Uiso 1 1 calc GR . . . .
C15 C 0.6219(12) 0.7568(5) 0.5329(7) 0.061(2) Uani 1 1 d . . . . .
H15A H 0.6030 0.7188 0.4755 0.091 Uiso 1 1 calc GR . . . .
H15B H 0.7046 0.7984 0.5272 0.091 Uiso 1 1 calc GR . . . .
H15C H 0.5163 0.7840 0.5332 0.091 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
Br2 C25 1.960(6) . ?
S2 O5 1.422(6) . ?
S2 O6 1.416(6) . ?
S2 N1 1.689(5) . ?
S2 C20 1.750(7) . ?
O7 C23 1.209(7) . ?
O8 C23 1.348(7) . ?
O8 C24 1.444(7) . ?
N1 C23 1.375(8) . ?
N1 C26 1.487(8) . ?
C16 C17 1.503(10) . ?
C17 C18 1.386(10) . ?
C17 C22 1.376(10) . ?
C18 C19 1.375(9) . ?
C19 C20 1.390(8) . ?
C20 C21 1.382(9) . ?
C21 C22 1.380(9) . ?
C24 C25 1.504(8) . ?
C25 C26 1.513(8) . ?
C26 C27 1.513(8) . ?
C27 C28 1.319(9) . ?
C28 C29 1.490(9) . ?
C28 C30 1.495(9) . ?
Br1 C10 1.950(6) . ?
S1 O1 1.428(4) . ?
S1 O2 1.429(5) . ?
S1 N2 1.684(5) . ?
S1 C5 1.750(6) . ?
O3 C8 1.201(7) . ?
O4 C8 1.348(6) . ?
O4 C9 1.445(7) . ?
N2 C8 1.391(7) . ?
N2 C11 1.481(7) . ?
C1 C2 1.497(9) . ?
C2 C3 1.392(10) . ?
C2 C7 1.395(9) . ?
C3 C4 1.375(9) . ?
C4 C5 1.391(9) . ?
C5 C6 1.387(8) . ?
C6 C7 1.377(9) . ?
C9 C10 1.499(8) . ?
C10 C11 1.525(8) . ?
C11 C12 1.508(8) . ?
C12 C13 1.306(9) . ?
C13 C14 1.505(10) . ?
C13 C15 1.497(10) . ?

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
O5 S2 N1 103.4(3) . . ?
O5 S2 C20 108.7(3) . . ?
O6 S2 O5 119.8(4) . . ?
O6 S2 N1 109.3(3) . . ?
O6 S2 C20 109.5(3) . . ?
N1 S2 C20 105.2(3) . . ?
C23 O8 C24 121.3(5) . . ?
C23 N1 S2 116.8(4) . . ?
C23 N1 C26 124.8(5) . . ?
C26 N1 S2 117.8(4) . . ?
C18 C17 C16 120.7(7) . . ?
C22 C17 C16 121.2(7) . . ?
C22 C17 C18 118.1(7) . . ?
C19 C18 C17 122.3(6) . . ?
C18 C19 C20 118.1(7) . . ?
C19 C20 S2 118.6(5) . . ?
C21 C20 S2 120.6(5) . . ?
C21 C20 C19 120.9(6) . . ?
C22 C21 C20 119.2(6) . . ?
C17 C22 C21 121.4(7) . . ?
O7 C23 O8 118.6(6) . . ?
O7 C23 N1 123.2(5) . . ?
O8 C23 N1 118.2(5) . . ?
O8 C24 C25 110.1(5) . . ?
C24 C25 Br2 110.9(4) . . ?
C24 C25 C26 109.6(5) . . ?
C26 C25 Br2 111.1(4) . . ?
N1 C26 C25 107.4(5) . . ?
N1 C26 C27 111.6(5) . . ?
C25 C26 C27 110.9(5) . . ?
C28 C27 C26 124.2(6) . . ?
C27 C28 C29 124.2(6) . . ?
C27 C28 C30 120.6(6) . . ?
C29 C28 C30 115.1(6) . . ?
O1 S1 O2 119.3(3) . . ?
O1 S1 N2 109.5(3) . . ?
O1 S1 C5 109.2(3) . . ?
O2 S1 N2 103.7(3) . . ?
O2 S1 C5 108.4(3) . . ?
N2 S1 C5 105.9(3) . . ?
C8 O4 C9 122.9(5) . . ?
C8 N2 S1 117.0(4) . . ?
C8 N2 C11 124.0(5) . . ?
C11 N2 S1 118.5(4) . . ?
C3 C2 C1 121.2(7) . . ?
C3 C2 C7 117.8(6) . . ?
C7 C2 C1 121.0(6) . . ?
C4 C3 C2 121.1(6) . . ?
C3 C4 C5 119.8(6) . . ?
C4 C5 S1 119.7(5) . . ?
C6 C5 S1 119.7(5) . . ?
C6 C5 C4 120.4(6) . . ?
C7 C6 C5 118.8(6) . . ?
C6 C7 C2 122.1(6) . . ?
O3 C8 O4 119.9(5) . . ?
O3 C8 N2 123.0(5) . . ?
O4 C8 N2 117.0(5) . . ?
O4 C9 C10 113.0(5) . . ?
C9 C10 Br1 110.7(4) . . ?
C9 C10 C11 107.8(5) . . ?
C11 C10 Br1 111.6(4) . . ?
N2 C11 C10 107.1(5) . . ?
N2 C11 C12 111.4(5) . . ?
C12 C11 C10 111.3(5) . . ?
C13 C12 C11 124.9(6) . . ?
C12 C13 C14 121.4(7) . . ?
C12 C13 C15 123.7(7) . . ?
C15 C13 C14 114.9(6) . . ?

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
Br2 C25 C26 N1 -70.8(5) . . . . ?
Br2 C25 C26 C27 167.1(4) . . . . ?
S2 N1 C23 O7 -5.7(8) . . . . ?
S2 N1 C23 O8 176.4(4) . . . . ?
S2 N1 C26 C25 162.5(4) . . . . ?
S2 N1 C26 C27 -75.7(6) . . . . ?
S2 C20 C21 C22 179.9(5) . . . . ?
O5 S2 N1 C23 176.3(5) . . . . ?
O5 S2 N1 C26 -12.5(5) . . . . ?
O5 S2 C20 C19 -33.9(6) . . . . ?
O5 S2 C20 C21 145.0(6) . . . . ?
O6 S2 N1 C23 -55.1(5) . . . . ?
O6 S2 N1 C26 116.1(5) . . . . ?
O6 S2 C20 C19 -166.3(5) . . . . ?
O6 S2 C20 C21 12.5(7) . . . . ?
O8 C24 C25 Br2 63.5(5) . . . . ?
O8 C24 C25 C26 -59.4(6) . . . . ?
N1 S2 C20 C19 76.4(5) . . . . ?
N1 S2 C20 C21 -104.7(6) . . . . ?
N1 C26 C27 C28 157.3(6) . . . . ?
C16 C17 C18 C19 179.2(7) . . . . ?
C16 C17 C22 C21 -178.5(7) . . . . ?
C17 C18 C19 C20 -1.1(10) . . . . ?
C18 C17 C22 C21 0.9(11) . . . . ?
C18 C19 C20 S2 -179.2(5) . . . . ?
C18 C19 C20 C21 1.9(9) . . . . ?
C19 C20 C21 C22 -1.3(10) . . . . ?
C20 S2 N1 C23 62.3(5) . . . . ?
C20 S2 N1 C26 -126.5(5) . . . . ?
C20 C21 C22 C17 -0.2(11) . . . . ?
C22 C17 C18 C19 -0.2(10) . . . . ?
C23 O8 C24 C25 39.0(7) . . . . ?
C23 N1 C26 C25 -27.0(7) . . . . ?
C23 N1 C26 C27 94.7(6) . . . . ?
C24 O8 C23 O7 170.3(5) . . . . ?
C24 O8 C23 N1 -11.8(7) . . . . ?
C24 C25 C26 N1 52.0(6) . . . . ?
C24 C25 C26 C27 -70.1(7) . . . . ?
C25 C26 C27 C28 -83.1(8) . . . . ?
C26 N1 C23 O7 -176.2(5) . . . . ?
C26 N1 C23 O8 5.9(8) . . . . ?
C26 C27 C28 C29 -2.0(11) . . . . ?
C26 C27 C28 C30 179.5(6) . . . . ?
Br1 C10 C11 N2 -65.6(5) . . . . ?
Br1 C10 C11 C12 172.5(4) . . . . ?
S1 N2 C8 O3 -3.7(8) . . . . ?
S1 N2 C8 O4 177.5(4) . . . . ?
S1 N2 C11 C10 153.4(4) . . . . ?
S1 N2 C11 C12 -84.7(5) . . . . ?
S1 C5 C6 C7 174.6(5) . . . . ?
O1 S1 N2 C8 -56.3(5) . . . . ?
O1 S1 N2 C11 116.4(4) . . . . ?
O1 S1 C5 C4 4.2(6) . . . . ?
O1 S1 C5 C6 -170.9(5) . . . . ?
O2 S1 N2 C8 175.3(4) . . . . ?
O2 S1 N2 C11 -12.0(5) . . . . ?
O2 S1 C5 C4 135.7(5) . . . . ?
O2 S1 C5 C6 -39.4(5) . . . . ?
O4 C9 C10 Br1 67.8(6) . . . . ?
O4 C9 C10 C11 -54.5(7) . . . . ?
N2 S1 C5 C4 -113.6(5) . . . . ?
N2 S1 C5 C6 71.3(5) . . . . ?
N2 C11 C12 C13 156.1(6) . . . . ?
C1 C2 C3 C4 176.5(7) . . . . ?
C1 C2 C7 C6 -176.2(6) . . . . ?
C2 C3 C4 C5 0.4(10) . . . . ?
C3 C2 C7 C6 2.2(10) . . . . ?
C3 C4 C5 S1 -174.3(5) . . . . ?
C3 C4 C5 C6 0.8(10) . . . . ?
C4 C5 C6 C7 -0.6(9) . . . . ?
C5 S1 N2 C8 61.3(5) . . . . ?
C5 S1 N2 C11 -126.0(4) . . . . ?
C5 C6 C7 C2 -1.0(10) . . . . ?
C7 C2 C3 C4 -1.8(10) . . . . ?
C8 O4 C9 C10 26.2(8) . . . . ?
C8 N2 C11 C10 -34.4(7) . . . . ?
C8 N2 C11 C12 87.5(6) . . . . ?
C9 O4 C8 O3 -178.7(5) . . . . ?
C9 O4 C8 N2 0.1(8) . . . . ?
C9 C10 C11 N2 56.2(6) . . . . ?
C9 C10 C11 C12 -65.7(7) . . . . ?
C10 C11 C12 C13 -84.5(8) . . . . ?
C11 N2 C8 O3 -176.0(6) . . . . ?
C11 N2 C8 O4 5.2(8) . . . . ?
C11 C12 C13 C14 177.2(6) . . . . ?
C11 C12 C13 C15 -1.8(11) . . . . ?

####################################################################### 
# 
# 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
_audit_block_doi                 10.5517/cc13vg0f
_database_code_depnum_ccdc_archive 'CCDC 1038314'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;
_audit_creation_date             2014-04-09
_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         'C15 H18 Br N O4 S'
_chemical_formula_sum            'C15 H18 Br N O4 S'
_chemical_formula_weight         388.27
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.900(2)
_cell_length_b                   17.232(3)
_cell_length_c                   8.4931(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1595.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5014
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4822
_cell_measurement_theta_min      1.8684
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.725
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9741
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         3.263
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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             2114
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0052
_diffrn_orient_matrix_UB_12      -0.0531
_diffrn_orient_matrix_UB_13      0.1050
_diffrn_orient_matrix_UB_21      -0.0738
_diffrn_orient_matrix_UB_22      0.0471
_diffrn_orient_matrix_UB_23      0.0274
_diffrn_orient_matrix_UB_31      -0.0344
_diffrn_orient_matrix_UB_32      -0.0424
_diffrn_orient_matrix_UB_33      -0.0197
_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         0.732
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3560
_reflns_number_total             3627
_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  'XL (Sheldrick, 2013)'
_computing_structure_solution    
;
'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 1447 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.011(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3627
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.089
_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)+(0.0350P)²+0.4567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0722
_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), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C11(H11), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
;
_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 0.43993(3) 0.66421(2) 0.71010(4) 0.03147(12) Uani 1 1 d . . . . .
S1 S 0.76221(7) 0.53271(4) 0.48826(9) 0.01927(16) Uani 1 1 d . . . . .
O1 O 0.7006(2) 0.74618(13) 0.6083(3) 0.0263(5) Uani 1 1 d . . . . .
O2 O 0.8530(2) 0.66566(14) 0.6528(3) 0.0253(5) Uani 1 1 d . . . . .
O3 O 0.8754(2) 0.54583(15) 0.4092(3) 0.0281(5) Uani 1 1 d . . . . .
O4 O 0.6713(2) 0.48540(13) 0.4128(3) 0.0271(5) Uani 1 1 d . . . . .
N1 N 0.6889(2) 0.61822(14) 0.5170(3) 0.0177(5) Uani 1 1 d . . . . .
C1 C 0.5751(3) 0.63126(18) 0.4273(4) 0.0188(6) Uani 1 1 d . . . . .
H1 H 0.5246 0.5843 0.4333 0.023 Uiso 1 1 calc R . . . .
C2 C 0.5060(3) 0.69761(19) 0.5062(4) 0.0239(7) Uani 1 1 d . . . . .
H2 H 0.4374 0.7128 0.4383 0.029 Uiso 1 1 calc R . . . .
C3 C 0.5887(3) 0.76592(19) 0.5261(4) 0.0278(8) Uani 1 1 d . . . . .
H3A H 0.6091 0.7867 0.4232 0.033 Uiso 1 1 calc R . . . .
H3B H 0.5458 0.8060 0.5843 0.033 Uiso 1 1 calc R . . . .
C4 C 0.7536(3) 0.67605(17) 0.5937(4) 0.0203(6) Uani 1 1 d . . . . .
C5 C 0.5962(3) 0.65098(18) 0.2546(4) 0.0214(7) Uani 1 1 d . . . . .
C6 C 0.7035(3) 0.6743(2) 0.2011(4) 0.0262(7) Uani 1 1 d . . . . .
H6 H 0.7675 0.6759 0.2735 0.031 Uiso 1 1 calc R . . . .
C7 C 0.7335(4) 0.6989(2) 0.0350(4) 0.0352(9) Uani 1 1 d . . . . .
H7A H 0.6641 0.6892 -0.0318 0.053 Uiso 1 1 calc GR . . . .
H7B H 0.8027 0.6698 -0.0023 0.053 Uiso 1 1 calc GR . . . .
H7C H 0.7527 0.7532 0.0335 0.053 Uiso 1 1 calc GR . . . .
C8 C 0.4825(4) 0.6431(3) 0.1565(5) 0.0452(11) Uani 1 1 d . . . . .
H8A H 0.4383 0.5975 0.1879 0.068 Uiso 1 1 calc GR . . . .
H8B H 0.5048 0.6389 0.0474 0.068 Uiso 1 1 calc GR . . . .
H8C H 0.4315 0.6880 0.1712 0.068 Uiso 1 1 calc GR . . . .
C9 C 0.7920(3) 0.49652(18) 0.6781(4) 0.0206(6) Uani 1 1 d . . . . .
C10 C 0.8885(3) 0.44418(18) 0.6889(4) 0.0214(7) Uani 1 1 d . . . . .
H10 H 0.9346 0.4314 0.6005 0.026 Uiso 1 1 calc R . . . .
C11 C 0.9149(3) 0.41131(18) 0.8336(4) 0.0240(7) Uani 1 1 d . . . . .
H11 H 0.9779 0.3752 0.8412 0.029 Uiso 1 1 calc R . . . .
C12 C 0.8490(3) 0.43123(19) 0.9682(4) 0.0245(7) Uani 1 1 d . . . . .
C13 C 0.7516(4) 0.4834(2) 0.9534(4) 0.0270(7) Uani 1 1 d . . . . .
H13 H 0.7061 0.4970 1.0419 0.032 Uiso 1 1 calc R . . . .
C14 C 0.7219(3) 0.51546(19) 0.8082(4) 0.0265(7) Uani 1 1 d . . . . .
H14 H 0.6557 0.5492 0.7987 0.032 Uiso 1 1 calc R . . . .
C15 C 0.8838(4) 0.3977(2) 1.1261(5) 0.0333(8) Uani 1 1 d . . . . .
H15A H 0.9326 0.3519 1.1107 0.050 Uiso 1 1 calc GR . . . .
H15B H 0.8108 0.3845 1.1834 0.050 Uiso 1 1 calc GR . . . .
H15C H 0.9301 0.4353 1.1846 0.050 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 C2 1.962(3) . ?
S1 O3 1.423(3) . ?
S1 O4 1.434(3) . ?
S1 N1 1.694(3) . ?
S1 C9 1.759(3) . ?
O1 C3 1.446(4) . ?
O1 C4 1.345(4) . ?
O2 C4 1.208(4) . ?
N1 C1 1.474(4) . ?
N1 C4 1.383(4) . ?
C1 C2 1.524(4) . ?
C1 C5 1.523(4) . ?
C2 C3 1.492(5) . ?
C5 C6 1.317(5) . ?
C5 C8 1.500(5) . ?
C6 C7 1.509(5) . ?
C9 C10 1.388(4) . ?
C9 C14 1.383(4) . ?
C10 C11 1.384(5) . ?
C11 C12 1.393(5) . ?
C12 C13 1.397(5) . ?
C12 C15 1.509(5) . ?
C13 C14 1.389(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 118.60(15) . . ?
O3 S1 N1 109.81(14) . . ?
O3 S1 C9 109.19(15) . . ?
O4 S1 N1 103.48(14) . . ?
O4 S1 C9 109.60(15) . . ?
N1 S1 C9 105.27(14) . . ?
C4 O1 C3 121.9(3) . . ?
C1 N1 S1 117.1(2) . . ?
C4 N1 S1 117.0(2) . . ?
C4 N1 C1 124.2(3) . . ?
N1 C1 C2 107.6(3) . . ?
N1 C1 C5 113.9(3) . . ?
C5 C1 C2 109.3(3) . . ?
C1 C2 Br1 110.5(2) . . ?
C3 C2 Br1 110.7(2) . . ?
C3 C2 C1 110.1(3) . . ?
O1 C3 C2 112.2(3) . . ?
O1 C4 N1 118.2(3) . . ?
O2 C4 O1 118.7(3) . . ?
O2 C4 N1 123.1(3) . . ?
C6 C5 C1 122.3(3) . . ?
C6 C5 C8 124.7(3) . . ?
C8 C5 C1 112.9(3) . . ?
C5 C6 C7 126.9(3) . . ?
C10 C9 S1 115.6(2) . . ?
C14 C9 S1 123.1(2) . . ?
C14 C9 C10 121.3(3) . . ?
C11 C10 C9 118.8(3) . . ?
C10 C11 C12 121.4(3) . . ?
C11 C12 C13 118.4(3) . . ?
C11 C12 C15 120.4(3) . . ?
C13 C12 C15 121.2(3) . . ?
C14 C13 C12 120.9(3) . . ?
C9 C14 C13 119.1(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 C2 C3 O1 68.4(3) . . . . ?
S1 N1 C1 C2 162.9(2) . . . . ?
S1 N1 C1 C5 -75.7(3) . . . . ?
S1 N1 C4 O1 175.5(2) . . . . ?
S1 N1 C4 O2 -7.3(4) . . . . ?
S1 C9 C10 C11 -177.9(2) . . . . ?
S1 C9 C14 C13 179.4(3) . . . . ?
O3 S1 N1 C1 111.5(2) . . . . ?
O3 S1 N1 C4 -54.4(3) . . . . ?
O3 S1 C9 C10 -38.8(3) . . . . ?
O3 S1 C9 C14 144.0(3) . . . . ?
O4 S1 N1 C1 -16.0(3) . . . . ?
O4 S1 N1 C4 178.1(2) . . . . ?
O4 S1 C9 C10 92.6(3) . . . . ?
O4 S1 C9 C14 -84.6(3) . . . . ?
N1 S1 C9 C10 -156.7(2) . . . . ?
N1 S1 C9 C14 26.1(3) . . . . ?
N1 C1 C2 Br1 -70.5(3) . . . . ?
N1 C1 C2 C3 52.0(3) . . . . ?
N1 C1 C5 C6 -17.1(4) . . . . ?
N1 C1 C5 C8 164.6(3) . . . . ?
C1 N1 C4 O1 10.6(4) . . . . ?
C1 N1 C4 O2 -172.1(3) . . . . ?
C1 C2 C3 O1 -54.1(4) . . . . ?
C1 C5 C6 C7 -177.0(3) . . . . ?
C2 C1 C5 C6 103.3(4) . . . . ?
C2 C1 C5 C8 -75.0(4) . . . . ?
C3 O1 C4 O2 172.8(3) . . . . ?
C3 O1 C4 N1 -9.9(4) . . . . ?
C4 O1 C3 C2 32.8(4) . . . . ?
C4 N1 C1 C2 -32.3(4) . . . . ?
C4 N1 C1 C5 89.1(4) . . . . ?
C5 C1 C2 Br1 165.3(2) . . . . ?
C5 C1 C2 C3 -72.1(3) . . . . ?
C8 C5 C6 C7 1.1(6) . . . . ?
C9 S1 N1 C1 -131.0(2) . . . . ?
C9 S1 N1 C4 63.0(3) . . . . ?
C9 C10 C11 C12 -1.7(5) . . . . ?
C10 C9 C14 C13 2.3(5) . . . . ?
C10 C11 C12 C13 2.4(5) . . . . ?
C10 C11 C12 C15 -176.8(3) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C12 C13 C14 C9 -1.6(5) . . . . ?
C14 C9 C10 C11 -0.7(5) . . . . ?
C15 C12 C13 C14 178.5(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_sa3324
_audit_block_doi                 10.5517/cc13vg1g
_database_code_depnum_ccdc_archive 'CCDC 1038315'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;
_audit_creation_date             2014-04-11
_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 H19 N O4 S'
_chemical_formula_sum            'C13 H19 N O4 S'
_chemical_formula_weight         285.35
_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'
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                   7.714(2)
_cell_length_b                   8.924(3)
_cell_length_c                   11.423(3)
_cell_angle_alpha                76.922(12)
_cell_angle_beta                 75.224(12)
_cell_angle_gamma                74.066(12)
_cell_volume                     720.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2678
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4777
_cell_measurement_theta_min      2.7900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.116
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12392
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.806
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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             3297
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0707
_diffrn_orient_matrix_UB_12      -0.0828
_diffrn_orient_matrix_UB_13      0.0845
_diffrn_orient_matrix_UB_21      0.1105
_diffrn_orient_matrix_UB_22      -0.0412
_diffrn_orient_matrix_UB_23      0.0077
_diffrn_orient_matrix_UB_31      0.0084
_diffrn_orient_matrix_UB_32      0.0761
_diffrn_orient_matrix_UB_33      0.0507
_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                3191
_reflns_number_total             3293
_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  'XL (Sheldrick, 2013)'
_computing_structure_solution    
;
'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.161
_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)+(0.0494P)²+0.3010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1198
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4A), C8(H8), C9(H9), C11(H11), C12(H12)
2.e Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C13(H13A,H13B,H13C)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_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
S1 S 0.91629(5) -0.01899(5) 0.32810(3) 0.02241(14) Uani 1 1 d . . . . .
O1 O 0.79248(17) -0.05386(14) 0.26804(11) 0.0281(3) Uani 1 1 d . . . . .
O2 O 1.00685(17) -0.14274(14) 0.41206(11) 0.0282(3) Uani 1 1 d . . . . .
O3 O 0.47259(17) 0.21512(15) 0.57178(11) 0.0291(3) Uani 1 1 d . . . . .
H3 H 0.3913 0.1742 0.6176 0.044 Uiso 1 1 calc GR . . . .
O4 O 0.52253(17) 0.51958(14) 0.34228(12) 0.0309(3) Uani 1 1 d . . . . .
H4 H 0.5211 0.6044 0.3593 0.046 Uiso 1 1 calc GR . . . .
N1 N 0.79937(19) 0.11788(16) 0.40585(12) 0.0238(3) Uani 1 1 d . . . . .
H1 H 0.8734 0.1572 0.4282 0.029 Uiso 1 1 d R . . . .
C1 C 0.6495(2) 0.24602(19) 0.36621(15) 0.0235(3) Uani 1 1 d . . . . .
H1A H 0.6486 0.2415 0.2815 0.028 Uiso 1 1 calc R . . . .
C2 C 0.6842(2) 0.40646(19) 0.36859(15) 0.0250(3) Uani 1 1 d . . . . .
H2 H 0.6978 0.4090 0.4511 0.030 Uiso 1 1 calc R . . . .
C3 C 0.8512(2) 0.4423(2) 0.27629(16) 0.0285(4) Uani 1 1 d . . . . .
H3A H 0.8642 0.4272 0.1963 0.034 Uiso 1 1 calc R . . . .
C4 C 0.9802(3) 0.4936(2) 0.30071(18) 0.0369(4) Uani 1 1 d . . . . .
H4A H 0.9718 0.5001 0.3822 0.044 Uiso 1 1 calc R . . . .
C5 C 1.1401(3) 0.5425(3) 0.2080(2) 0.0456(5) Uani 1 1 d . . . . .
H5A H 1.1384 0.5240 0.1288 0.068 Uiso 1 1 calc GR . . . .
H5B H 1.2532 0.4820 0.2317 0.068 Uiso 1 1 calc GR . . . .
H5C H 1.1311 0.6529 0.2042 0.068 Uiso 1 1 calc GR . . . .
C6 C 0.4664(2) 0.2200(2) 0.44700(16) 0.0274(4) Uani 1 1 d . . . . .
H6A H 0.3663 0.3053 0.4232 0.033 Uiso 1 1 calc R . . . .
H6B H 0.4457 0.1213 0.4376 0.033 Uiso 1 1 calc R . . . .
C7 C 1.0879(2) 0.05322(19) 0.21313(14) 0.0233(3) Uani 1 1 d . . . . .
C8 C 1.2510(2) 0.0507(2) 0.24460(16) 0.0311(4) Uani 1 1 d . . . . .
H8 H 1.2712 0.0055 0.3231 0.037 Uiso 1 1 calc R . . . .
C9 C 1.3831(3) 0.1162(2) 0.15776(17) 0.0346(4) Uani 1 1 d . . . . .
H9 H 1.4930 0.1138 0.1784 0.041 Uiso 1 1 calc R . . . .
C10 C 1.3548(3) 0.1856(2) 0.04015(16) 0.0306(4) Uani 1 1 d . . . . .
C11 C 1.1924(3) 0.1836(2) 0.00965(16) 0.0322(4) Uani 1 1 d . . . . .
H11 H 1.1733 0.2268 -0.0694 0.039 Uiso 1 1 calc R . . . .
C12 C 1.0582(2) 0.1181(2) 0.09540(15) 0.0286(4) Uani 1 1 d . . . . .
H12 H 0.9497 0.1177 0.0742 0.034 Uiso 1 1 calc R . . . .
C13 C 1.4997(3) 0.2604(3) -0.0508(2) 0.0443(5) Uani 1 1 d . . . . .
H13A H 1.5091 0.3512 -0.0231 0.066 Uiso 1 1 calc GR . . . .
H13B H 1.4660 0.2923 -0.1296 0.066 Uiso 1 1 calc GR . . . .
H13C H 1.6163 0.1852 -0.0576 0.066 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
S1 O1 1.4401(12) . ?
S1 O2 1.4374(12) . ?
S1 N1 1.6037(14) . ?
S1 C7 1.7584(16) . ?
O3 C6 1.429(2) . ?
O4 C2 1.424(2) . ?
N1 C1 1.468(2) . ?
C1 C2 1.534(2) . ?
C1 C6 1.523(2) . ?
C2 C3 1.501(2) . ?
C3 C4 1.314(3) . ?
C4 C5 1.502(3) . ?
C7 C8 1.386(2) . ?
C7 C12 1.389(2) . ?
C8 C9 1.383(2) . ?
C9 C10 1.391(3) . ?
C10 C11 1.388(3) . ?
C10 C13 1.509(2) . ?
C11 C12 1.389(2) . ?

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 107.17(7) . . ?
O1 S1 C7 107.60(8) . . ?
O2 S1 O1 119.00(8) . . ?
O2 S1 N1 106.09(7) . . ?
O2 S1 C7 107.64(8) . . ?
N1 S1 C7 109.05(8) . . ?
C1 N1 S1 123.91(11) . . ?
N1 C1 C2 109.89(13) . . ?
N1 C1 C6 109.14(13) . . ?
C6 C1 C2 112.86(14) . . ?
O4 C2 C1 105.04(13) . . ?
O4 C2 C3 110.39(13) . . ?
C3 C2 C1 113.04(14) . . ?
C4 C3 C2 124.53(17) . . ?
C3 C4 C5 125.42(19) . . ?
O3 C6 C1 108.35(13) . . ?
C8 C7 S1 118.20(12) . . ?
C8 C7 C12 120.67(15) . . ?
C12 C7 S1 121.06(13) . . ?
C9 C8 C7 119.18(16) . . ?
C8 C9 C10 121.31(17) . . ?
C9 C10 C13 119.74(18) . . ?
C11 C10 C9 118.57(16) . . ?
C11 C10 C13 121.70(17) . . ?
C10 C11 C12 121.00(16) . . ?
C7 C12 C11 119.24(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 S1 0.82 2.93 3.6874(15) 154.1 2_656
O3 H3 O1 0.82 2.03 2.8487(17) 174.8 2_656
O4 H4 O3 0.82 1.96 2.7731(19) 169.7 2_666
N1 H1 O2 0.86 2.21 2.9303(19) 141.1 2_756

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 -126.77(13) . . . . ?
S1 N1 C1 C6 108.98(14) . . . . ?
S1 C7 C8 C9 -175.85(14) . . . . ?
S1 C7 C12 C11 175.62(14) . . . . ?
O1 S1 N1 C1 -35.02(14) . . . . ?
O1 S1 C7 C8 -161.03(14) . . . . ?
O1 S1 C7 C12 22.01(17) . . . . ?
O2 S1 N1 C1 -163.14(12) . . . . ?
O2 S1 C7 C8 -31.63(16) . . . . ?
O2 S1 C7 C12 151.40(14) . . . . ?
O4 C2 C3 C4 110.5(2) . . . . ?
N1 S1 C7 C8 83.04(16) . . . . ?
N1 S1 C7 C12 -93.92(15) . . . . ?
N1 C1 C2 O4 -173.71(12) . . . . ?
N1 C1 C2 C3 65.87(18) . . . . ?
N1 C1 C6 O3 58.23(17) . . . . ?
C1 C2 C3 C4 -132.14(19) . . . . ?
C2 C1 C6 O3 -64.26(18) . . . . ?
C2 C3 C4 C5 -174.79(18) . . . . ?
C6 C1 C2 O4 -51.64(17) . . . . ?
C6 C1 C2 C3 -172.06(14) . . . . ?
C7 S1 N1 C1 81.18(14) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C7 C12 C11 -1.3(3) . . . . ?
C8 C9 C10 C11 -2.0(3) . . . . ?
C8 C9 C10 C13 178.10(19) . . . . ?
C9 C10 C11 C12 1.9(3) . . . . ?
C10 C11 C12 C7 -0.3(3) . . . . ?
C12 C7 C8 C9 1.1(3) . . . . ?
C13 C10 C11 C12 -178.25(18) . . . . ?

####################################################################### 
# 
# 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_sa3352
_audit_block_doi                 10.5517/cc13vg2h
_database_code_depnum_ccdc_archive 'CCDC 1038316'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;
_audit_creation_date             2014-05-04
_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 H19 N O3 S, H2 O'
_chemical_formula_sum            'C13 H21 N O4 S'
_chemical_formula_weight         287.37
_chemical_absolute_configuration ad
_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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.036(2)
_cell_length_b                   7.3432(15)
_cell_length_c                   10.826(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.23(3)
_cell_angle_gamma                90
_cell_volume                     743.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2772
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4846
_cell_measurement_theta_min      2.0182
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.613
_exptl_crystal_size_mid          0.59
_exptl_crystal_size_min          0.128
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8617
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         3.431
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_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             1833
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.1005
_diffrn_orient_matrix_UB_12      -0.0034
_diffrn_orient_matrix_UB_13      0.0363
_diffrn_orient_matrix_UB_21      -0.0084
_diffrn_orient_matrix_UB_22      -0.1312
_diffrn_orient_matrix_UB_23      -0.0356
_diffrn_orient_matrix_UB_31      -0.0028
_diffrn_orient_matrix_UB_32      -0.0258
_diffrn_orient_matrix_UB_33      0.0956
_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         0.800
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                3235
_reflns_number_total             3285
_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         0.214
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1391 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3285
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.076
_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)+(0.0336P)²+0.1168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0671
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C8(H8)
2.c Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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
S1 S 0.48290(5) 0.39761(6) 0.34478(4) 0.02387(12) Uani 1 1 d . . . . .
O1 O 0.41971(15) 0.2864(2) 0.22877(15) 0.0334(3) Uani 1 1 d . . . . .
O2 O 0.46455(15) 0.3471(2) 0.46600(15) 0.0347(4) Uani 1 1 d . . . . .
O3 O 0.08142(17) 0.6277(2) 0.05745(16) 0.0382(4) Uani 1 1 d . . . . .
H3 H 0.0976 0.5258 0.0904 0.057 Uiso 1 1 calc GR . . . .
N1 N 0.41439(17) 0.5986(2) 0.31075(15) 0.0220(3) Uani 1 1 d . . . . .
H1 H 0.4531 0.6703 0.3769 0.026 Uiso 1 1 d R . . . .
C1 C 1.1198(2) 0.4562(3) 0.4654(2) 0.0339(5) Uani 1 1 d . . . . .
H1A H 1.1424 0.4123 0.3918 0.051 Uiso 1 1 calc GR . . . .
H1B H 1.1709 0.3860 0.5429 0.051 Uiso 1 1 calc GR . . . .
H1C H 1.1468 0.5819 0.4811 0.051 Uiso 1 1 calc GR . . . .
C2 C 0.9611(2) 0.4378(3) 0.4343(2) 0.0267(4) Uani 1 1 d . . . . .
C3 C 0.8701(2) 0.3701(3) 0.3125(2) 0.0301(4) Uani 1 1 d . . . . .
H3A H 0.9077 0.3352 0.2493 0.036 Uiso 1 1 calc R . . . .
C4 C 0.7236(2) 0.3540(3) 0.2842(2) 0.0285(4) Uani 1 1 d . . . . .
H4 H 0.6637 0.3083 0.2029 0.034 Uiso 1 1 calc R . . . .
C5 C 0.66838(18) 0.4069(3) 0.37851(18) 0.0234(3) Uani 1 1 d . . . . .
C6 C 0.7569(2) 0.4755(3) 0.50062(19) 0.0265(4) Uani 1 1 d . . . . .
H6 H 0.7188 0.5123 0.5631 0.032 Uiso 1 1 calc R . . . .
C7 C 0.9023(2) 0.4882(3) 0.5277(2) 0.0286(4) Uani 1 1 d . . . . .
H7 H 0.9619 0.5312 0.6099 0.034 Uiso 1 1 calc R . . . .
C8 C 0.4001(2) 0.6932(3) 0.18530(18) 0.0237(4) Uani 1 1 d . . . . .
H8 H 0.3717 0.6037 0.1132 0.028 Uiso 1 1 calc R . . . .
C9 C 0.5379(2) 0.7801(3) 0.1915(2) 0.0293(4) Uani 1 1 d . . . . .
H9 H 0.5760 0.8700 0.2551 0.035 Uiso 1 1 calc R . . . .
C10 C 0.6092(2) 0.7392(3) 0.1141(2) 0.0357(5) Uani 1 1 d . . . . .
H10 H 0.5693 0.6537 0.0476 0.043 Uiso 1 1 calc R . . . .
C11 C 0.7504(3) 0.8211(4) 0.1261(3) 0.0502(7) Uani 1 1 d . . . . .
H11A H 0.7772 0.9114 0.1949 0.075 Uiso 1 1 calc GR . . . .
H11B H 0.7425 0.8769 0.0435 0.075 Uiso 1 1 calc GR . . . .
H11C H 0.8219 0.7274 0.1474 0.075 Uiso 1 1 calc GR . . . .
C12 C 0.2806(2) 0.8346(3) 0.1577(2) 0.0278(4) Uani 1 1 d . . . . .
H12A H 0.3130 0.9302 0.2237 0.033 Uiso 1 1 calc R . . . .
H12B H 0.2642 0.8894 0.0719 0.033 Uiso 1 1 calc R . . . .
C13 C 0.1397(2) 0.7617(3) 0.1585(2) 0.0298(4) Uani 1 1 d . . . . .
H13A H 0.1543 0.7080 0.2443 0.036 Uiso 1 1 calc R . . . .
H13B H 0.0724 0.8613 0.1447 0.036 Uiso 1 1 calc R . . . .
O4 O 0.11347(18) 0.2826(2) 0.15735(16) 0.0341(3) Uani 1 1 d . . . . .
H4A H 0.201(4) 0.260(5) 0.174(3) 0.050(8) Uiso 1 1 d . . . . .
H4B H 0.056(4) 0.216(5) 0.087(3) 0.060(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4385(15) . ?
S1 O2 1.4383(15) . ?
S1 N1 1.6135(16) . ?
S1 C5 1.7637(18) . ?
O3 C13 1.429(3) . ?
N1 C8 1.486(2) . ?
C1 C2 1.509(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.393(3) . ?
C3 C4 1.394(3) . ?
C4 C5 1.382(3) . ?
C5 C6 1.393(3) . ?
C6 C7 1.383(3) . ?
C8 C9 1.502(3) . ?
C8 C12 1.532(3) . ?
C9 C10 1.319(3) . ?
C10 C11 1.501(3) . ?
C12 C13 1.514(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
O1 S1 N1 107.65(9) . . ?
O1 S1 C5 107.53(9) . . ?
O2 S1 O1 119.25(10) . . ?
O2 S1 N1 105.03(9) . . ?
O2 S1 C5 107.18(9) . . ?
N1 S1 C5 110.01(9) . . ?
C8 N1 S1 121.91(12) . . ?
C3 C2 C1 121.27(19) . . ?
C7 C2 C1 120.34(19) . . ?
C7 C2 C3 118.39(18) . . ?
C4 C3 C2 121.03(18) . . ?
C5 C4 C3 119.12(18) . . ?
C4 C5 S1 120.76(15) . . ?
C4 C5 C6 120.94(17) . . ?
C6 C5 S1 118.25(14) . . ?
C7 C6 C5 119.15(18) . . ?
C6 C7 C2 121.35(19) . . ?
N1 C8 C9 112.04(15) . . ?
N1 C8 C12 107.73(15) . . ?
C9 C8 C12 111.35(17) . . ?
C10 C9 C8 125.3(2) . . ?
C9 C10 C11 124.5(2) . . ?
C13 C12 C8 115.19(17) . . ?
O3 C13 C12 111.31(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O4 0.82 1.91 2.728(2) 173.7 .
N1 H1 O2 0.86 2.06 2.919(2) 177.1 2_656
O4 H4A S1 0.85(3) 2.94(3) 3.623(2) 139(3) .
O4 H4A O1 0.85(3) 2.06(3) 2.885(2) 163(3) .
O4 H4B O3 0.91(4) 1.79(4) 2.689(2) 167(3) 2_545

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 C8 C9 -80.55(19) . . . . ?
S1 N1 C8 C12 156.65(14) . . . . ?
S1 C5 C6 C7 -178.41(15) . . . . ?
O1 S1 N1 C8 -46.28(16) . . . . ?
O1 S1 C5 C4 15.2(2) . . . . ?
O1 S1 C5 C6 -167.25(16) . . . . ?
O2 S1 N1 C8 -174.34(14) . . . . ?
O2 S1 C5 C4 144.52(17) . . . . ?
O2 S1 C5 C6 -37.89(19) . . . . ?
N1 S1 C5 C4 -101.81(18) . . . . ?
N1 S1 C5 C6 75.79(18) . . . . ?
N1 C8 C9 C10 118.6(2) . . . . ?
N1 C8 C12 C13 -53.0(2) . . . . ?
C1 C2 C3 C4 -179.78(19) . . . . ?
C1 C2 C7 C6 178.87(19) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C2 C7 C6 -1.3(3) . . . . ?
C3 C4 C5 S1 177.47(16) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C5 S1 N1 C8 70.62(16) . . . . ?
C5 C6 C7 C2 1.5(3) . . . . ?
C7 C2 C3 C4 0.4(3) . . . . ?
C8 C9 C10 C11 -176.9(2) . . . . ?
C8 C12 C13 O3 -61.9(2) . . . . ?
C9 C8 C12 C13 -176.20(16) . . . . ?
C12 C8 C9 C10 -120.6(2) . . . . ?

####################################################################### 
# 
# 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_sa3453
_audit_block_doi                 10.5517/cc13vg3j
_database_code_depnum_ccdc_archive 'CCDC 1038317'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;
_audit_creation_date             2014-06-17
_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         'C20 H24 Br N O5 S2'
_chemical_formula_sum            'C20 H24 Br N O5 S2'
_chemical_formula_weight         502.43
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.6597(12)
_cell_length_b                   15.690(3)
_cell_length_c                   24.567(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2181.6(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6744
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4672
_cell_measurement_theta_min      1.5400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.107
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            14174
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.467
_diffrn_reflns_theta_min         2.596
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_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             2901
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0109
_diffrn_orient_matrix_UB_12      0.0642
_diffrn_orient_matrix_UB_13      -0.1642
_diffrn_orient_matrix_UB_21      -0.0635
_diffrn_orient_matrix_UB_22      -0.0043
_diffrn_orient_matrix_UB_23      0.0025
_diffrn_orient_matrix_UB_31      -0.0020
_diffrn_orient_matrix_UB_32      0.0378
_diffrn_orient_matrix_UB_33      0.0149
_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         0.696
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                4457
_reflns_number_total             4865
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 1581 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.024(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4865
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.104
_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)+(0.0156P)²+1.6129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0809
_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:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C15(H15), C16(H16),
 C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.02822(9) 0.26904(3) 0.57258(2) 0.03604(14) Uani 1 1 d . . . . .
S1 S 0.6541(2) 0.49863(9) 0.49872(5) 0.0277(3) Uani 1 1 d . . . . .
S2 S 0.5163(2) 0.28480(8) 0.72998(4) 0.0286(3) Uani 1 1 d . . . . .
O1 O 0.9028(6) 0.5037(2) 0.50153(16) 0.0407(9) Uani 1 1 d . . . . .
O2 O 0.5413(7) 0.4828(2) 0.44784(12) 0.0332(8) Uani 1 1 d . . . . .
O3 O 0.5886(5) 0.4252(2) 0.54048(13) 0.0266(8) Uani 1 1 d . . . . .
O4 O 0.7505(6) 0.2861(3) 0.70708(14) 0.0362(9) Uani 1 1 d . . . . .
O5 O 0.4379(7) 0.2125(2) 0.76064(13) 0.0372(9) Uani 1 1 d . . . . .
N1 N 0.3309(8) 0.2931(3) 0.67986(17) 0.0290(10) Uani 1 1 d . . . . .
C1 C 0.2181(10) 0.8058(4) 0.6070(2) 0.0417(14) Uani 1 1 d . . . . .
H1A H 0.3106 0.8559 0.6000 0.062 Uiso 1 1 calc GR . . . .
H1B H 0.2114 0.7956 0.6455 0.062 Uiso 1 1 calc GR . . . .
H1C H 0.0610 0.8139 0.5932 0.062 Uiso 1 1 calc GR . . . .
C2 C 0.3295(8) 0.7307(3) 0.57928(19) 0.0278(10) Uani 1 1 d . . . . .
C3 C 0.2238(8) 0.6931(3) 0.5343(2) 0.0269(11) Uani 1 1 d . . . . .
H3 H 0.0830 0.7155 0.5211 0.032 Uiso 1 1 calc R . . . .
C4 C 0.3219(8) 0.6230(3) 0.50857(19) 0.0268(11) Uani 1 1 d . . . . .
H4 H 0.2488 0.5987 0.4785 0.032 Uiso 1 1 calc R . . . .
C5 C 0.5307(8) 0.5902(3) 0.52855(18) 0.0238(10) Uani 1 1 d . . . . .
C6 C 0.6416(8) 0.6256(3) 0.5740(2) 0.0309(11) Uani 1 1 d . . . . .
H6 H 0.7814 0.6025 0.5874 0.037 Uiso 1 1 calc R . . . .
C7 C 0.5401(9) 0.6953(3) 0.5986(2) 0.0319(11) Uani 1 1 d . . . . .
H7 H 0.6133 0.7195 0.6288 0.038 Uiso 1 1 calc R . . . .
C8 C 0.3471(8) 0.3936(3) 0.53841(19) 0.0259(11) Uani 1 1 d . . . . .
H8A H 0.3136 0.3685 0.5032 0.031 Uiso 1 1 calc R . . . .
H8B H 0.2356 0.4394 0.5450 0.031 Uiso 1 1 calc R . . . .
C9 C 0.3316(8) 0.3274(3) 0.58273(18) 0.0240(10) Uani 1 1 d . . . . .
H9 H 0.4594 0.2860 0.5776 0.029 Uiso 1 1 calc R . . . .
C10 C 0.3492(8) 0.3642(3) 0.64051(19) 0.0253(11) Uani 1 1 d . . . . .
H10 H 0.5085 0.3879 0.6443 0.030 Uiso 1 1 calc R . . . .
C11 C 0.1793(9) 0.4349(3) 0.65327(19) 0.0271(11) Uani 1 1 d . . . . .
H11 H 0.0190 0.4244 0.6482 0.032 Uiso 1 1 calc R . . . .
C12 C 0.2416(10) 0.5106(3) 0.67114(19) 0.0291(11) Uani 1 1 d . . . . .
H12 H 0.4027 0.5217 0.6734 0.035 Uiso 1 1 calc R . . . .
C13 C 0.0776(10) 0.5808(3) 0.6883(2) 0.0359(13) Uani 1 1 d . . . . .
H13A H 0.0998 0.6293 0.6650 0.054 Uiso 1 1 calc GR . . . .
H13B H 0.1108 0.5965 0.7253 0.054 Uiso 1 1 calc GR . . . .
H13C H -0.0829 0.5614 0.6856 0.054 Uiso 1 1 calc GR . . . .
C14 C 0.4893(9) 0.3764(3) 0.77119(17) 0.0253(10) Uani 1 1 d . . . . .
C15 C 0.6639(9) 0.4376(3) 0.7715(2) 0.0307(12) Uani 1 1 d . . . . .
H15 H 0.7975 0.4313 0.7498 0.037 Uiso 1 1 calc R . . . .
C16 C 0.6383(9) 0.5087(3) 0.8045(2) 0.0322(12) Uani 1 1 d . . . . .
H16 H 0.7550 0.5505 0.8045 0.039 Uiso 1 1 calc R . . . .
C17 C 0.4406(9) 0.5187(3) 0.83764(19) 0.0284(11) Uani 1 1 d . . . . .
C18 C 0.2672(9) 0.4564(3) 0.8364(2) 0.0307(12) Uani 1 1 d . . . . .
H18 H 0.1339 0.4623 0.8582 0.037 Uiso 1 1 calc R . . . .
C19 C 0.2889(9) 0.3857(3) 0.8031(2) 0.0296(12) Uani 1 1 d . . . . .
H19 H 0.1702 0.3448 0.8022 0.036 Uiso 1 1 calc R . . . .
C20 C 0.4194(10) 0.5953(3) 0.8741(2) 0.0413(14) Uani 1 1 d . . . . .
H20A H 0.5722 0.6208 0.8789 0.062 Uiso 1 1 calc GR . . . .
H20B H 0.3581 0.5781 0.9088 0.062 Uiso 1 1 calc GR . . . .
H20C H 0.3142 0.6360 0.8578 0.062 Uiso 1 1 calc GR . . . .
H1 H 0.196(9) 0.282(4) 0.686(2) 0.037(16) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C9 1.962(4) . ?
S1 O1 1.411(3) . ?
S1 O2 1.426(3) . ?
S1 O3 1.587(3) . ?
S1 C5 1.757(5) . ?
S2 O4 1.440(4) . ?
S2 O5 1.432(3) . ?
S2 N1 1.623(4) . ?
S2 C14 1.765(5) . ?
O3 C8 1.455(5) . ?
N1 C10 1.480(6) . ?
C1 C2 1.499(7) . ?
C2 C3 1.388(6) . ?
C2 C7 1.398(7) . ?
C3 C4 1.384(7) . ?
C4 C5 1.380(6) . ?
C5 C6 1.397(6) . ?
C6 C7 1.376(7) . ?
C8 C9 1.508(6) . ?
C9 C10 1.536(6) . ?
C10 C11 1.501(6) . ?
C11 C12 1.315(7) . ?
C12 C13 1.501(7) . ?
C14 C15 1.378(7) . ?
C14 C19 1.387(7) . ?
C15 C16 1.387(7) . ?
C16 C17 1.392(7) . ?
C17 C18 1.385(7) . ?
C17 C20 1.505(7) . ?
C18 C19 1.382(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 119.9(2) . . ?
O1 S1 O3 104.0(2) . . ?
O1 S1 C5 109.3(2) . . ?
O2 S1 O3 109.6(2) . . ?
O2 S1 C5 109.3(2) . . ?
O3 S1 C5 103.4(2) . . ?
O4 S2 N1 107.3(2) . . ?
O4 S2 C14 107.0(2) . . ?
O5 S2 O4 120.1(2) . . ?
O5 S2 N1 105.2(2) . . ?
O5 S2 C14 108.4(2) . . ?
N1 S2 C14 108.3(2) . . ?
C8 O3 S1 116.4(3) . . ?
C10 N1 S2 120.7(3) . . ?
C3 C2 C1 120.9(5) . . ?
C3 C2 C7 118.0(5) . . ?
C7 C2 C1 121.0(5) . . ?
C4 C3 C2 121.9(4) . . ?
C5 C4 C3 118.6(4) . . ?
C4 C5 S1 119.9(4) . . ?
C4 C5 C6 121.4(4) . . ?
C6 C5 S1 118.7(4) . . ?
C7 C6 C5 118.7(5) . . ?
C6 C7 C2 121.4(5) . . ?
O3 C8 C9 105.3(4) . . ?
C8 C9 Br1 106.3(3) . . ?
C8 C9 C10 113.9(4) . . ?
C10 C9 Br1 110.5(3) . . ?
N1 C10 C9 108.4(4) . . ?
N1 C10 C11 112.1(4) . . ?
C11 C10 C9 115.4(4) . . ?
C12 C11 C10 124.4(5) . . ?
C11 C12 C13 126.2(5) . . ?
C15 C14 S2 120.6(4) . . ?
C15 C14 C19 120.6(4) . . ?
C19 C14 S2 118.8(4) . . ?
C14 C15 C16 119.3(5) . . ?
C15 C16 C17 121.1(5) . . ?
C16 C17 C20 120.1(5) . . ?
C18 C17 C16 118.5(5) . . ?
C18 C17 C20 121.4(5) . . ?
C19 C18 C17 121.1(5) . . ?
C18 C19 C14 119.5(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.80(5) 2.58(5) 3.354(6) 166(6) 1_455

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 C10 N1 60.3(4) . . . . ?
Br1 C9 C10 C11 -66.4(5) . . . . ?
S1 O3 C8 C9 -178.3(3) . . . . ?
S1 C5 C6 C7 -177.5(4) . . . . ?
S2 N1 C10 C9 132.5(4) . . . . ?
S2 N1 C10 C11 -98.9(4) . . . . ?
S2 C14 C15 C16 -179.7(4) . . . . ?
S2 C14 C19 C18 178.9(4) . . . . ?
O1 S1 O3 C8 -168.0(3) . . . . ?
O1 S1 C5 C4 146.9(4) . . . . ?
O1 S1 C5 C6 -36.2(4) . . . . ?
O2 S1 O3 C8 -38.6(4) . . . . ?
O2 S1 C5 C4 13.9(4) . . . . ?
O2 S1 C5 C6 -169.3(4) . . . . ?
O3 S1 C5 C4 -102.8(4) . . . . ?
O3 S1 C5 C6 74.1(4) . . . . ?
O3 C8 C9 Br1 -170.0(3) . . . . ?
O3 C8 C9 C10 68.2(5) . . . . ?
O4 S2 N1 C10 -54.0(4) . . . . ?
O4 S2 C14 C15 7.4(4) . . . . ?
O4 S2 C14 C19 -172.8(4) . . . . ?
O5 S2 N1 C10 177.0(4) . . . . ?
O5 S2 C14 C15 138.4(4) . . . . ?
O5 S2 C14 C19 -41.8(4) . . . . ?
N1 S2 C14 C15 -108.0(4) . . . . ?
N1 S2 C14 C19 71.9(4) . . . . ?
N1 C10 C11 C12 110.6(5) . . . . ?
C1 C2 C3 C4 -179.2(5) . . . . ?
C1 C2 C7 C6 179.0(5) . . . . ?
C2 C3 C4 C5 0.1(7) . . . . ?
C3 C2 C7 C6 0.3(7) . . . . ?
C3 C4 C5 S1 177.3(4) . . . . ?
C3 C4 C5 C6 0.5(7) . . . . ?
C4 C5 C6 C7 -0.7(7) . . . . ?
C5 S1 O3 C8 77.9(4) . . . . ?
C5 C6 C7 C2 0.3(8) . . . . ?
C7 C2 C3 C4 -0.5(7) . . . . ?
C8 C9 C10 N1 179.8(4) . . . . ?
C8 C9 C10 C11 53.2(6) . . . . ?
C9 C10 C11 C12 -124.6(5) . . . . ?
C10 C11 C12 C13 -175.2(5) . . . . ?
C14 S2 N1 C10 61.2(4) . . . . ?
C14 C15 C16 C17 0.7(8) . . . . ?
C15 C14 C19 C18 -1.3(7) . . . . ?
C15 C16 C17 C18 -1.0(8) . . . . ?
C15 C16 C17 C20 178.5(5) . . . . ?
C16 C17 C18 C19 0.2(8) . . . . ?
C17 C18 C19 C14 1.0(8) . . . . ?
C19 C14 C15 C16 0.4(7) . . . . ?
C20 C17 C18 C19 -179.4(5) . . . . ?

####################################################################### 
# 
# 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_sa3504
_audit_block_doi                 10.5517/cc13vg4k
_database_code_depnum_ccdc_archive 'CCDC 1038318'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;
_audit_creation_date             2014-07-09
_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         'C15 H19 N O5 S'
_chemical_formula_sum            'C15 H19 N O5 S'
_chemical_formula_weight         325.37
_chemical_absolute_configuration ad
_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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.116(2)
_cell_length_b                   14.954(5)
_cell_length_c                   13.474(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.642(3)
_cell_angle_gamma                90
_cell_volume                     1633.4(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5834
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4838
_cell_measurement_theta_min      1.5129
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18681
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.992
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_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             3862
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.1205
_diffrn_orient_matrix_UB_12      0.0035
_diffrn_orient_matrix_UB_13      -0.0264
_diffrn_orient_matrix_UB_21      -0.0053
_diffrn_orient_matrix_UB_22      0.0585
_diffrn_orient_matrix_UB_23      0.0319
_diffrn_orient_matrix_UB_31      0.0115
_diffrn_orient_matrix_UB_32      0.0359
_diffrn_orient_matrix_UB_33      -0.0640
_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         0.909
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                7152
_reflns_number_total             7346
_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         0.192
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 3191 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         7346
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.065
_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)+(0.0315P)²+0.3089P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0735
_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:
 C1A(H1A), C4A(H4A), C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C7A(H7A), C10A(H10A), C11A(H11A), C13A(H13A), C14A(H14A), C6(H6),
 C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C5A(H5AA,H5AB,H5AC), C8A(H8AA,H8AB,H8AC), C15A(H15A,H15B,H15C), C5(H5A,H5B,
 H5C), C8(H8A,H8B,H8C), C15(H15D,H15E,H15F)
;
_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
S1A S 0.81172(7) 0.72052(4) 0.39643(4) 0.02523(12) Uani 1 1 d . . . . .
O1A O 1.1647(2) 0.55155(12) 0.39428(14) 0.0356(4) Uani 1 1 d . . . . .
O2A O 0.9048(3) 0.52267(12) 0.43265(15) 0.0416(5) Uani 1 1 d . . . . .
O3A O 0.8440(2) 0.80430(12) 0.35057(13) 0.0322(4) Uani 1 1 d . . . . .
O4A O 0.6847(2) 0.66323(13) 0.35596(13) 0.0358(4) Uani 1 1 d . . . . .
O5A O 1.2368(2) 0.72061(14) 0.53894(12) 0.0381(4) Uani 1 1 d . . . . .
N1A N 0.9893(2) 0.66587(13) 0.39199(14) 0.0256(4) Uani 1 1 d . . . . .
C1A C 1.1464(3) 0.70992(16) 0.37052(16) 0.0254(5) Uani 1 1 d . . . . .
H1A H 1.1350 0.7417 0.3070 0.030 Uiso 1 1 calc R . . . .
C2A C 1.2568(3) 0.62715(17) 0.35972(19) 0.0321(5) Uani 1 1 d . . . . .
H2AA H 1.2832 0.6188 0.2908 0.039 Uiso 1 1 calc R . . . .
H2AB H 1.3590 0.6341 0.3993 0.039 Uiso 1 1 calc R . . . .
C3A C 1.0077(3) 0.57452(16) 0.40897(18) 0.0296(5) Uani 1 1 d . . . . .
C4A C 1.2092(3) 0.77377(17) 0.45194(19) 0.0294(5) Uani 1 1 d . . . . .
H4A H 1.1234 0.8181 0.4640 0.035 Uiso 1 1 calc R . . . .
C5A C 1.2682(4) 0.7736(2) 0.6263(2) 0.0490(8) Uani 1 1 d . . . . .
H5AA H 1.3680 0.8072 0.6198 0.074 Uiso 1 1 calc GR . . . .
H5AB H 1.2799 0.7352 0.6833 0.074 Uiso 1 1 calc GR . . . .
H5AC H 1.1779 0.8140 0.6344 0.074 Uiso 1 1 calc GR . . . .
C6A C 1.3615(3) 0.82125(17) 0.4211(2) 0.0318(5) Uani 1 1 d . . . . .
H6A H 1.4474 0.7870 0.3979 0.038 Uiso 1 1 calc R . . . .
C7A C 1.3804(3) 0.90796(19) 0.4248(2) 0.0419(7) Uani 1 1 d . . . . .
H7A H 1.2936 0.9416 0.4477 0.050 Uiso 1 1 calc R . . . .
C8A C 1.5314(4) 0.9574(2) 0.3951(3) 0.0519(8) Uani 1 1 d . . . . .
H8AA H 1.5020 0.9983 0.3423 0.078 Uiso 1 1 calc GR . . . .
H8AB H 1.6114 0.9155 0.3728 0.078 Uiso 1 1 calc GR . . . .
H8AC H 1.5775 0.9901 0.4511 0.078 Uiso 1 1 calc GR . . . .
C9A C 0.7761(3) 0.73751(15) 0.52236(16) 0.0243(5) Uani 1 1 d . . . . .
C10A C 0.7034(3) 0.66941(16) 0.57448(18) 0.0306(5) Uani 1 1 d . . . . .
H10A H 0.6746 0.6158 0.5432 0.037 Uiso 1 1 calc R . . . .
C11A C 0.6741(3) 0.68236(16) 0.67417(18) 0.0332(5) Uani 1 1 d . . . . .
H11A H 0.6259 0.6367 0.7097 0.040 Uiso 1 1 calc R . . . .
C12A C 0.7156(3) 0.76231(16) 0.72199(17) 0.0260(5) Uani 1 1 d . . . . .
C13A C 0.7855(3) 0.82987(16) 0.66753(18) 0.0288(5) Uani 1 1 d . . . . .
H13A H 0.8120 0.8840 0.6983 0.035 Uiso 1 1 calc R . . . .
C14A C 0.8167(3) 0.81845(16) 0.56781(18) 0.0272(5) Uani 1 1 d . . . . .
H14A H 0.8640 0.8642 0.5321 0.033 Uiso 1 1 calc R . . . .
C15A C 0.6822(4) 0.77481(18) 0.83074(18) 0.0344(6) Uani 1 1 d . . . . .
H15A H 0.5659 0.7699 0.8397 0.052 Uiso 1 1 calc GR . . . .
H15B H 0.7200 0.8328 0.8521 0.052 Uiso 1 1 calc GR . . . .
H15C H 0.7396 0.7296 0.8693 0.052 Uiso 1 1 calc GR . . . .
S1 S 1.03424(7) 0.54236(4) 0.11455(4) 0.02727(13) Uani 1 1 d . . . . .
O1 O 0.6765(2) 0.39299(13) 0.18404(14) 0.0378(4) Uani 1 1 d . . . . .
O2 O 0.9145(2) 0.34498(13) 0.12451(15) 0.0414(5) Uani 1 1 d . . . . .
O3 O 1.0218(2) 0.63324(12) 0.14702(13) 0.0341(4) Uani 1 1 d . . . . .
O4 O 1.1632(2) 0.48697(13) 0.15521(13) 0.0363(4) Uani 1 1 d . . . . .
O5 O 0.5782(3) 0.50850(12) 0.00539(13) 0.0378(4) Uani 1 1 d . . . . .
N1 N 0.8571(3) 0.49671(13) 0.14343(14) 0.0288(4) Uani 1 1 d . . . . .
C1 C 0.7070(3) 0.54911(17) 0.15952(17) 0.0294(5) Uani 1 1 d . . . . .
H1 H 0.7327 0.5988 0.2050 0.035 Uiso 1 1 calc R . . . .
C2 C 0.6063(4) 0.47797(19) 0.2118(2) 0.0377(6) Uani 1 1 d . . . . .
H2A H 0.6153 0.4860 0.2832 0.045 Uiso 1 1 calc R . . . .
H2B H 0.4909 0.4813 0.1899 0.045 Uiso 1 1 calc R . . . .
C3 C 0.8263(3) 0.40463(17) 0.14779(18) 0.0323(5) Uani 1 1 d . . . . .
C4 C 0.6262(3) 0.58438(17) 0.06308(18) 0.0306(5) Uani 1 1 d . . . . .
H4 H 0.7076 0.6188 0.0275 0.037 Uiso 1 1 calc R . . . .
C5 C 0.5309(5) 0.5301(2) -0.0948(2) 0.0576(9) Uani 1 1 d . . . . .
H5A H 0.6249 0.5523 -0.1278 0.086 Uiso 1 1 calc GR . . . .
H5B H 0.4464 0.5750 -0.0958 0.086 Uiso 1 1 calc GR . . . .
H5C H 0.4897 0.4774 -0.1283 0.086 Uiso 1 1 calc GR . . . .
C6 C 0.4826(3) 0.64412(17) 0.08428(19) 0.0333(5) Uani 1 1 d . . . . .
H6 H 0.3842 0.6167 0.1000 0.040 Uiso 1 1 calc R . . . .
C7 C 0.4856(4) 0.73186(18) 0.0823(2) 0.0385(6) Uani 1 1 d . . . . .
H7 H 0.5824 0.7589 0.0634 0.046 Uiso 1 1 calc R . . . .
C8 C 0.3463(4) 0.7921(2) 0.1079(3) 0.0493(7) Uani 1 1 d . . . . .
H8A H 0.3201 0.8313 0.0530 0.074 Uiso 1 1 calc GR . . . .
H8B H 0.3783 0.8268 0.1655 0.074 Uiso 1 1 calc GR . . . .
H8C H 0.2514 0.7566 0.1215 0.074 Uiso 1 1 calc GR . . . .
C9 C 1.0394(3) 0.54066(17) -0.01542(16) 0.0267(4) Uani 1 1 d . . . . .
C10 C 1.0496(4) 0.45959(18) -0.0641(2) 0.0378(6) Uani 1 1 d . . . . .
H10 H 1.0521 0.4062 -0.0287 0.045 Uiso 1 1 calc R . . . .
C11 C 1.0563(4) 0.45930(19) -0.1672(2) 0.0407(6) Uani 1 1 d . . . . .
H11 H 1.0625 0.4051 -0.2007 0.049 Uiso 1 1 calc R . . . .
C12 C 1.0537(3) 0.5385(2) -0.22075(17) 0.0339(5) Uani 1 1 d . . . . .
C13 C 1.0461(3) 0.61857(18) -0.17013(19) 0.0341(6) Uani 1 1 d . . . . .
H13 H 1.0460 0.6719 -0.2056 0.041 Uiso 1 1 calc R . . . .
C14 C 1.0387(3) 0.62106(17) -0.06727(18) 0.0299(5) Uani 1 1 d . . . . .
H14 H 1.0333 0.6753 -0.0339 0.036 Uiso 1 1 calc R . . . .
C15 C 1.0583(4) 0.5368(2) -0.33268(19) 0.0465(7) Uani 1 1 d . . . . .
H15D H 1.0790 0.4768 -0.3544 0.070 Uiso 1 1 calc GR . . . .
H15E H 1.1446 0.5754 -0.3535 0.070 Uiso 1 1 calc GR . . . .
H15F H 0.9544 0.5569 -0.3613 0.070 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
S1A O3A 1.4265(19) . ?
S1A O4A 1.4290(18) . ?
S1A N1A 1.660(2) . ?
S1A C9A 1.753(2) . ?
O1A C2A 1.444(3) . ?
O1A C3A 1.343(3) . ?
O2A C3A 1.194(3) . ?
O5A C4A 1.425(3) . ?
O5A C5A 1.433(3) . ?
N1A C1A 1.476(3) . ?
N1A C3A 1.392(3) . ?
C1A C2A 1.539(3) . ?
C1A C4A 1.524(3) . ?
C4A C6A 1.501(4) . ?
C6A C7A 1.306(4) . ?
C7A C8A 1.502(4) . ?
C9A C10A 1.384(3) . ?
C9A C14A 1.389(3) . ?
C10A C11A 1.388(3) . ?
C11A C12A 1.392(3) . ?
C12A C13A 1.385(3) . ?
C12A C15A 1.514(3) . ?
C13A C14A 1.389(3) . ?
S1 O3 1.4326(19) . ?
S1 O4 1.4241(19) . ?
S1 N1 1.654(2) . ?
S1 C9 1.754(2) . ?
O1 C2 1.448(3) . ?
O1 C3 1.342(3) . ?
O2 C3 1.195(3) . ?
O5 C4 1.420(3) . ?
O5 C5 1.423(3) . ?
N1 C1 1.473(3) . ?
N1 C3 1.401(3) . ?
C1 C2 1.532(4) . ?
C1 C4 1.523(3) . ?
C4 C6 1.506(4) . ?
C6 C7 1.313(4) . ?
C7 C8 1.497(4) . ?
C9 C10 1.383(4) . ?
C9 C14 1.390(3) . ?
C10 C11 1.393(4) . ?
C11 C12 1.387(4) . ?
C12 C13 1.380(4) . ?
C12 C15 1.511(3) . ?
C13 C14 1.391(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
O3A S1A O4A 120.31(12) . . ?
O3A S1A N1A 103.89(10) . . ?
O3A S1A C9A 109.50(11) . . ?
O4A S1A N1A 107.64(11) . . ?
O4A S1A C9A 107.95(11) . . ?
N1A S1A C9A 106.75(10) . . ?
C3A O1A C2A 110.86(19) . . ?
C4A O5A C5A 112.5(2) . . ?
C1A N1A S1A 123.13(16) . . ?
C3A N1A S1A 124.35(17) . . ?
C3A N1A C1A 112.5(2) . . ?
N1A C1A C2A 99.89(19) . . ?
N1A C1A C4A 113.68(18) . . ?
C4A C1A C2A 113.3(2) . . ?
O1A C2A C1A 106.65(19) . . ?
O1A C3A N1A 108.8(2) . . ?
O2A C3A O1A 123.6(2) . . ?
O2A C3A N1A 127.6(2) . . ?
O5A C4A C1A 106.1(2) . . ?
O5A C4A C6A 113.1(2) . . ?
C6A C4A C1A 110.4(2) . . ?
C7A C6A C4A 123.7(2) . . ?
C6A C7A C8A 125.0(3) . . ?
C10A C9A S1A 118.52(18) . . ?
C10A C9A C14A 121.0(2) . . ?
C14A C9A S1A 120.45(18) . . ?
C9A C10A C11A 119.0(2) . . ?
C10A C11A C12A 121.3(2) . . ?
C11A C12A C15A 120.3(2) . . ?
C13A C12A C11A 118.5(2) . . ?
C13A C12A C15A 121.2(2) . . ?
C12A C13A C14A 121.3(2) . . ?
C9A C14A C13A 118.9(2) . . ?
O3 S1 N1 104.21(11) . . ?
O3 S1 C9 108.90(11) . . ?
O4 S1 O3 119.68(11) . . ?
O4 S1 N1 107.48(11) . . ?
O4 S1 C9 108.95(12) . . ?
N1 S1 C9 106.85(11) . . ?
C3 O1 C2 110.7(2) . . ?
C4 O5 C5 113.2(2) . . ?
C1 N1 S1 123.29(17) . . ?
C3 N1 S1 125.07(18) . . ?
C3 N1 C1 111.5(2) . . ?
N1 C1 C2 99.2(2) . . ?
N1 C1 C4 112.66(19) . . ?
C4 C1 C2 114.5(2) . . ?
O1 C2 C1 105.5(2) . . ?
O1 C3 N1 108.0(2) . . ?
O2 C3 O1 124.2(2) . . ?
O2 C3 N1 127.7(2) . . ?
O5 C4 C1 106.7(2) . . ?
O5 C4 C6 112.5(2) . . ?
C6 C4 C1 110.5(2) . . ?
C7 C6 C4 125.0(3) . . ?
C6 C7 C8 125.5(3) . . ?
C10 C9 S1 119.43(19) . . ?
C10 C9 C14 121.2(2) . . ?
C14 C9 S1 119.30(19) . . ?
C9 C10 C11 118.8(2) . . ?
C12 C11 C10 121.0(2) . . ?
C11 C12 C15 120.3(3) . . ?
C13 C12 C11 118.9(2) . . ?
C13 C12 C15 120.8(2) . . ?
C12 C13 C14 121.4(2) . . ?
C9 C14 C13 118.6(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
S1A N1A C1A C2A -171.43(16) . . . . ?
S1A N1A C1A C4A 67.6(2) . . . . ?
S1A N1A C3A O1A 176.71(15) . . . . ?
S1A N1A C3A O2A -3.2(4) . . . . ?
S1A C9A C10A C11A -179.8(2) . . . . ?
S1A C9A C14A C13A 179.44(18) . . . . ?
O3A S1A N1A C1A 14.9(2) . . . . ?
O3A S1A N1A C3A -165.86(19) . . . . ?
O3A S1A C9A C10A 164.31(19) . . . . ?
O3A S1A C9A C14A -14.2(2) . . . . ?
O4A S1A N1A C1A 143.54(17) . . . . ?
O4A S1A N1A C3A -37.2(2) . . . . ?
O4A S1A C9A C10A 31.7(2) . . . . ?
O4A S1A C9A C14A -146.84(19) . . . . ?
O5A C4A C6A C7A -112.3(3) . . . . ?
N1A S1A C9A C10A -83.8(2) . . . . ?
N1A S1A C9A C14A 97.7(2) . . . . ?
N1A C1A C2A O1A -10.9(2) . . . . ?
N1A C1A C4A O5A 61.7(3) . . . . ?
N1A C1A C4A C6A -175.5(2) . . . . ?
C1A N1A C3A O1A -4.0(3) . . . . ?
C1A N1A C3A O2A 176.1(2) . . . . ?
C1A C4A C6A C7A 129.0(3) . . . . ?
C2A O1A C3A O2A 176.1(2) . . . . ?
C2A O1A C3A N1A -3.9(3) . . . . ?
C2A C1A C4A O5A -51.4(3) . . . . ?
C2A C1A C4A C6A 71.4(3) . . . . ?
C3A O1A C2A C1A 9.8(3) . . . . ?
C3A N1A C1A C2A 9.3(2) . . . . ?
C3A N1A C1A C4A -111.7(2) . . . . ?
C4A C1A C2A O1A 110.3(2) . . . . ?
C4A C6A C7A C8A 179.6(3) . . . . ?
C5A O5A C4A C1A -169.6(2) . . . . ?
C5A O5A C4A C6A 69.2(3) . . . . ?
C9A S1A N1A C1A -100.78(18) . . . . ?
C9A S1A N1A C3A 78.5(2) . . . . ?
C9A C10A C11A C12A 0.4(4) . . . . ?
C10A C9A C14A C13A 1.0(4) . . . . ?
C10A C11A C12A C13A 0.8(4) . . . . ?
C10A C11A C12A C15A 179.9(2) . . . . ?
C11A C12A C13A C14A -1.1(4) . . . . ?
C12A C13A C14A C9A 0.2(4) . . . . ?
C14A C9A C10A C11A -1.3(4) . . . . ?
C15A C12A C13A C14A 179.8(2) . . . . ?
S1 N1 C1 C2 -164.28(17) . . . . ?
S1 N1 C1 C4 74.2(2) . . . . ?
S1 N1 C3 O1 173.30(16) . . . . ?
S1 N1 C3 O2 -6.4(4) . . . . ?
S1 C9 C10 C11 -179.0(2) . . . . ?
S1 C9 C14 C13 178.73(19) . . . . ?
O3 S1 N1 C1 21.4(2) . . . . ?
O3 S1 N1 C3 -164.08(19) . . . . ?
O3 S1 C9 C10 -179.4(2) . . . . ?
O3 S1 C9 C14 2.8(2) . . . . ?
O4 S1 N1 C1 149.35(18) . . . . ?
O4 S1 N1 C3 -36.1(2) . . . . ?
O4 S1 C9 C10 48.5(2) . . . . ?
O4 S1 C9 C14 -129.4(2) . . . . ?
O5 C4 C6 C7 -139.2(3) . . . . ?
N1 S1 C9 C10 -67.4(2) . . . . ?
N1 S1 C9 C14 114.8(2) . . . . ?
N1 C1 C2 O1 -21.5(2) . . . . ?
N1 C1 C4 O5 62.5(3) . . . . ?
N1 C1 C4 C6 -174.9(2) . . . . ?
C1 N1 C3 O1 -11.6(3) . . . . ?
C1 N1 C3 O2 168.7(2) . . . . ?
C1 C4 C6 C7 101.7(3) . . . . ?
C2 O1 C3 O2 175.8(2) . . . . ?
C2 O1 C3 N1 -3.9(3) . . . . ?
C2 C1 C4 O5 -49.9(3) . . . . ?
C2 C1 C4 C6 72.6(3) . . . . ?
C3 O1 C2 C1 17.0(3) . . . . ?
C3 N1 C1 C2 20.5(2) . . . . ?
C3 N1 C1 C4 -101.0(2) . . . . ?
C4 C1 C2 O1 98.7(2) . . . . ?
C4 C6 C7 C8 -176.9(3) . . . . ?
C5 O5 C4 C1 -168.1(3) . . . . ?
C5 O5 C4 C6 70.6(3) . . . . ?
C9 S1 N1 C1 -93.83(19) . . . . ?
C9 S1 N1 C3 80.7(2) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
C10 C9 C14 C13 0.9(4) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C10 C11 C12 C15 -179.1(3) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C9 0.2(4) . . . . ?
C14 C9 C10 C11 -1.2(4) . . . . ?
C15 C12 C13 C14 178.8(2) . . . . ?

####################################################################### 
# 
# 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_sa3759
_audit_block_doi                 10.5517/cc13vg7n
_database_code_depnum_ccdc_archive 'CCDC 1038321'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;
_audit_creation_date             2014-12-02
_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         'C19 H18 Br N O4 S'
_chemical_formula_sum            'C19 H18 Br N O4 S'
_chemical_formula_weight         436.31
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.963(2)
_cell_length_b                   11.336(3)
_cell_length_c                   20.402(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1841.7(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5985
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4797
_cell_measurement_theta_min      0.9980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.370
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.27
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12167
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         3.126
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.987
_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             2418
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.1235
_diffrn_orient_matrix_UB_12      -0.0052
_diffrn_orient_matrix_UB_13      -0.0223
_diffrn_orient_matrix_UB_21      0.0075
_diffrn_orient_matrix_UB_22      0.0851
_diffrn_orient_matrix_UB_23      0.0221
_diffrn_orient_matrix_UB_31      0.0079
_diffrn_orient_matrix_UB_32      -0.0128
_diffrn_orient_matrix_UB_33      0.0467
_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         0.741
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                4032
_reflns_number_total             4159
_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         0.237
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 1588 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.018(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.123
_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)+(0.0164P)²+0.8072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0620
_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), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14),
 C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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 0.39930(5) 0.30537(3) 0.85487(2) 0.03301(10) Uani 1 1 d . . . . .
S1 S 0.86866(10) 0.25032(7) 0.76684(4) 0.01957(16) Uani 1 1 d . . . . .
O1 O 0.4903(3) 0.4430(2) 0.71323(12) 0.0251(5) Uani 1 1 d . . . . .
O2 O 0.7560(3) 0.4845(2) 0.72855(13) 0.0276(6) Uani 1 1 d . . . . .
O3 O 0.9876(3) 0.2895(2) 0.71942(11) 0.0274(5) Uani 1 1 d . . . . .
O4 O 0.8513(3) 0.12645(19) 0.77901(12) 0.0263(5) Uani 1 1 d . . . . .
N1 N 0.6753(3) 0.2925(2) 0.74212(12) 0.0178(5) Uani 1 1 d . . . . .
C1 C 0.3783(4) 0.2622(3) 0.76231(14) 0.0197(6) Uani 1 1 d . . . . .
H1 H 0.2852 0.2063 0.7575 0.024 Uiso 1 1 calc R . . . .
C2 C 0.5393(4) 0.2034(3) 0.73928(14) 0.0179(6) Uani 1 1 d . . . . .
H2 H 0.5667 0.1384 0.7691 0.021 Uiso 1 1 calc R . . . .
C3 C 0.6471(4) 0.4107(3) 0.72798(16) 0.0208(7) Uani 1 1 d . . . . .
C4 C 0.3427(4) 0.3698(3) 0.72111(17) 0.0242(7) Uani 1 1 d . . . . .
H4A H 0.3031 0.3451 0.6783 0.029 Uiso 1 1 calc R . . . .
H4B H 0.2543 0.4156 0.7416 0.029 Uiso 1 1 calc R . . . .
C5 C 0.5130(4) 0.1546(3) 0.67147(16) 0.0225(7) Uani 1 1 d . . . . .
H5 H 0.4349 0.0940 0.6672 0.027 Uiso 1 1 calc R . . . .
C6 C 0.5898(4) 0.1891(3) 0.61748(14) 0.0234(6) Uani 1 1 d . . . . .
H6 H 0.6735 0.2456 0.6222 0.028 Uiso 1 1 calc R . . . .
C7 C 0.5563(4) 0.1472(3) 0.55043(16) 0.0232(7) Uani 1 1 d . . . . .
C8 C 0.4598(5) 0.0461(3) 0.53697(18) 0.0279(8) Uani 1 1 d . . . . .
H8 H 0.4172 0.0013 0.5714 0.033 Uiso 1 1 calc R . . . .
C9 C 0.4277(5) 0.0125(3) 0.47281(17) 0.0323(9) Uani 1 1 d . . . . .
H9 H 0.3652 -0.0551 0.4645 0.039 Uiso 1 1 calc R . . . .
C10 C 0.4884(5) 0.0796(3) 0.42070(18) 0.0327(9) Uani 1 1 d . . . . .
H10 H 0.4665 0.0573 0.3777 0.039 Uiso 1 1 calc R . . . .
C11 C 0.5818(5) 0.1798(3) 0.43376(16) 0.0326(8) Uani 1 1 d . . . . .
H11 H 0.6209 0.2259 0.3993 0.039 Uiso 1 1 calc R . . . .
C12 C 0.6175(5) 0.2119(3) 0.49762(15) 0.0285(7) Uani 1 1 d . . . . .
H12 H 0.6836 0.2781 0.5054 0.034 Uiso 1 1 calc R . . . .
C13 C 0.9064(4) 0.3218(3) 0.84161(14) 0.0212(6) Uani 1 1 d . . . . .
C14 C 0.9752(4) 0.4352(3) 0.84335(17) 0.0231(7) Uani 1 1 d . . . . .
H14 H 0.9930 0.4772 0.8048 0.028 Uiso 1 1 calc R . . . .
C15 C 1.0163(5) 0.4839(3) 0.90366(18) 0.0268(8) Uani 1 1 d . . . . .
H15 H 1.0616 0.5594 0.9052 0.032 Uiso 1 1 calc R . . . .
C16 C 0.9912(5) 0.4225(3) 0.96156(17) 0.0289(8) Uani 1 1 d . . . . .
C17 C 0.9223(5) 0.3100(4) 0.95853(16) 0.0349(8) Uani 1 1 d . . . . .
H17 H 0.9050 0.2679 0.9971 0.042 Uiso 1 1 calc R . . . .
C18 C 0.8790(5) 0.2594(3) 0.89907(16) 0.0296(8) Uani 1 1 d . . . . .
H18 H 0.8320 0.1844 0.8977 0.035 Uiso 1 1 calc R . . . .
C19 C 1.0437(6) 0.4746(4) 1.0264(2) 0.0423(11) Uani 1 1 d . . . . .
H19A H 1.1639 0.4803 1.0281 0.063 Uiso 1 1 calc GR . . . .
H19B H 1.0051 0.4248 1.0614 0.063 Uiso 1 1 calc GR . . . .
H19C H 0.9954 0.5517 1.0311 0.063 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 C1 1.958(3) . ?
S1 O3 1.425(2) . ?
S1 O4 1.433(2) . ?
S1 N1 1.689(3) . ?
S1 C13 1.754(3) . ?
O1 C3 1.336(4) . ?
O1 C4 1.448(4) . ?
O2 C3 1.205(4) . ?
N1 C2 1.482(4) . ?
N1 C3 1.390(4) . ?
C1 C2 1.519(4) . ?
C1 C4 1.508(4) . ?
C2 C5 1.505(4) . ?
C5 C6 1.319(4) . ?
C6 C7 1.473(4) . ?
C7 C8 1.407(5) . ?
C7 C12 1.392(5) . ?
C8 C9 1.387(5) . ?
C9 C10 1.394(5) . ?
C10 C11 1.384(6) . ?
C11 C12 1.382(5) . ?
C13 C14 1.397(4) . ?
C13 C18 1.386(4) . ?
C14 C15 1.388(5) . ?
C15 C16 1.386(5) . ?
C16 C17 1.390(5) . ?
C16 C19 1.508(5) . ?
C17 C18 1.385(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 119.19(15) . . ?
O3 S1 N1 108.36(14) . . ?
O3 S1 C13 109.42(15) . . ?
O4 S1 N1 103.93(14) . . ?
O4 S1 C13 108.59(15) . . ?
N1 S1 C13 106.58(14) . . ?
C3 O1 C4 125.2(2) . . ?
C2 N1 S1 119.0(2) . . ?
C3 N1 S1 118.8(2) . . ?
C3 N1 C2 122.1(3) . . ?
C2 C1 Br1 109.6(2) . . ?
C4 C1 Br1 110.6(2) . . ?
C4 C1 C2 109.9(3) . . ?
N1 C2 C1 107.8(2) . . ?
N1 C2 C5 112.9(3) . . ?
C5 C2 C1 109.2(2) . . ?
O1 C3 N1 117.5(3) . . ?
O2 C3 O1 119.0(3) . . ?
O2 C3 N1 123.5(3) . . ?
O1 C4 C1 111.9(3) . . ?
C6 C5 C2 126.4(3) . . ?
C5 C6 C7 126.6(3) . . ?
C8 C7 C6 122.9(3) . . ?
C12 C7 C6 119.1(3) . . ?
C12 C7 C8 118.0(3) . . ?
C9 C8 C7 120.5(3) . . ?
C8 C9 C10 120.4(4) . . ?
C11 C10 C9 119.2(3) . . ?
C12 C11 C10 120.5(3) . . ?
C11 C12 C7 121.3(3) . . ?
C14 C13 S1 121.0(2) . . ?
C18 C13 S1 118.2(2) . . ?
C18 C13 C14 120.6(3) . . ?
C15 C14 C13 118.7(3) . . ?
C16 C15 C14 121.5(3) . . ?
C15 C16 C17 118.7(3) . . ?
C15 C16 C19 120.8(4) . . ?
C17 C16 C19 120.5(3) . . ?
C18 C17 C16 121.1(3) . . ?
C17 C18 C13 119.3(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 C1 C2 N1 -65.4(3) . . . . ?
Br1 C1 C2 C5 171.7(2) . . . . ?
Br1 C1 C4 O1 74.2(3) . . . . ?
S1 N1 C2 C1 141.6(2) . . . . ?
S1 N1 C2 C5 -97.8(3) . . . . ?
S1 N1 C3 O1 -175.2(2) . . . . ?
S1 N1 C3 O2 4.7(4) . . . . ?
S1 C13 C14 C15 -174.5(3) . . . . ?
S1 C13 C18 C17 174.2(3) . . . . ?
O3 S1 N1 C2 128.7(2) . . . . ?
O3 S1 N1 C3 -54.2(3) . . . . ?
O3 S1 C13 C14 29.9(3) . . . . ?
O3 S1 C13 C18 -145.0(3) . . . . ?
O4 S1 N1 C2 1.0(2) . . . . ?
O4 S1 N1 C3 178.1(2) . . . . ?
O4 S1 C13 C14 161.5(3) . . . . ?
O4 S1 C13 C18 -13.4(3) . . . . ?
N1 S1 C13 C14 -87.1(3) . . . . ?
N1 S1 C13 C18 98.0(3) . . . . ?
N1 C2 C5 C6 -4.6(5) . . . . ?
C1 C2 C5 C6 115.3(4) . . . . ?
C2 N1 C3 O1 1.8(4) . . . . ?
C2 N1 C3 O2 -178.4(3) . . . . ?
C2 C1 C4 O1 -47.0(4) . . . . ?
C2 C5 C6 C7 -175.6(3) . . . . ?
C3 O1 C4 C1 13.1(4) . . . . ?
C3 N1 C2 C1 -35.4(4) . . . . ?
C3 N1 C2 C5 85.3(3) . . . . ?
C4 O1 C3 O2 -169.1(3) . . . . ?
C4 O1 C3 N1 10.8(5) . . . . ?
C4 C1 C2 N1 56.3(3) . . . . ?
C4 C1 C2 C5 -66.6(3) . . . . ?
C5 C6 C7 C8 -13.5(6) . . . . ?
C5 C6 C7 C12 164.3(4) . . . . ?
C6 C7 C8 C9 178.0(3) . . . . ?
C6 C7 C12 C11 -176.5(3) . . . . ?
C7 C8 C9 C10 -1.0(6) . . . . ?
C8 C7 C12 C11 1.4(5) . . . . ?
C8 C9 C10 C11 0.3(6) . . . . ?
C9 C10 C11 C12 1.3(6) . . . . ?
C10 C11 C12 C7 -2.1(6) . . . . ?
C12 C7 C8 C9 0.2(5) . . . . ?
C13 S1 N1 C2 -113.6(2) . . . . ?
C13 S1 N1 C3 63.5(3) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C13 C18 C17 -0.8(6) . . . . ?
C14 C15 C16 C17 -0.4(6) . . . . ?
C14 C15 C16 C19 177.3(4) . . . . ?
C15 C16 C17 C18 0.0(6) . . . . ?
C16 C17 C18 C13 0.6(6) . . . . ?
C18 C13 C14 C15 0.3(5) . . . . ?
C19 C16 C17 C18 -177.7(4) . . . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
