# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

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

data_5e
_database_code_depnum_ccdc_archive 'CCDC 1546836'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H19 Cl2 N O3 S'
_chemical_formula_sum            'C31 H19 Cl2 N O3 S'
_chemical_formula_weight         556.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7443(10)
_cell_length_b                   11.9610(14)
_cell_length_c                   13.2912(13)
_cell_angle_alpha                79.913(3)
_cell_angle_beta                 70.808(3)
_cell_angle_gamma                75.349(4)
_cell_volume                     1263.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5690
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.05

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.376
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17424
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.282
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4913
_reflns_number_gt                3227
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+0.1065P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4913
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.7770(3) 1.05754(18) 1.01474(16) 0.0374(5) Uani 1 1 d . . . . .
C2 C 0.8118(3) 1.16116(19) 0.96013(19) 0.0508(6) Uani 1 1 d . . . . .
H2 H 0.8065 1.1817 0.8904 0.061 Uiso 1 1 calc R U . . .
C3 C 0.8551(3) 1.2348(2) 1.0117(2) 0.0600(7) Uani 1 1 d . . . . .
H3 H 0.8774 1.3056 0.9758 0.072 Uiso 1 1 calc R U . . .
C4 C 0.8657(3) 1.2056(2) 1.1137(2) 0.0594(7) Uani 1 1 d . . . . .
H4 H 0.8953 1.2565 1.1458 0.071 Uiso 1 1 calc R U . . .
C5 C 0.8331(3) 1.1023(2) 1.16891(19) 0.0518(6) Uani 1 1 d . . . . .
H5 H 0.8411 1.0820 1.2381 0.062 Uiso 1 1 calc R U . . .
C6 C 0.7878(3) 1.02822(18) 1.11888(17) 0.0413(5) Uani 1 1 d . . . . .
C7 C 0.7128(3) 0.87378(18) 1.05813(15) 0.0377(5) Uani 1 1 d . . . . .
C8 C 0.7141(2) 0.93958(18) 0.88762(15) 0.0363(5) Uani 1 1 d . . . . .
C9 C 0.7182(3) 1.02342(19) 0.79279(16) 0.0392(5) Uani 1 1 d . . . . .
C10 C 0.7705(3) 0.97981(18) 0.68639(16) 0.0399(5) Uani 1 1 d . . . . .
C11 C 0.8926(3) 0.88192(19) 0.65888(16) 0.0441(6) Uani 1 1 d . . . . .
H11 H 0.9467 0.8417 0.7083 0.053 Uiso 1 1 calc R U . . .
C12 C 0.9365(3) 0.8421(2) 0.55888(17) 0.0472(6) Uani 1 1 d . . . . .
H12 H 1.0212 0.7773 0.5407 0.057 Uiso 1 1 calc R U . . .
C13 C 0.8525(3) 0.9000(2) 0.48697(17) 0.0506(6) Uani 1 1 d . . . . .
C14 C 0.9898(4) 0.7594(2) 0.3626(2) 0.0737(8) Uani 1 1 d . . . . .
H14A H 1.0994 0.7630 0.3602 0.111 Uiso 1 1 calc R U . . .
H14B H 0.9912 0.7429 0.2941 0.111 Uiso 1 1 calc R U . . .
H14C H 0.9526 0.6990 0.4163 0.111 Uiso 1 1 calc R U . . .
C15 C 0.7309(3) 0.9992(2) 0.51356(18) 0.0585(7) Uani 1 1 d . . . . .
H15 H 0.6750 1.0384 0.4648 0.070 Uiso 1 1 calc R U . . .
C16 C 0.6925(3) 1.0396(2) 0.61032(17) 0.0511(6) Uani 1 1 d . . . . .
H16 H 0.6135 1.1078 0.6260 0.061 Uiso 1 1 calc R U . . .
C17 C 0.6696(3) 0.6305(2) 0.89397(18) 0.0486(6) Uani 1 1 d . . . . .
C18 C 0.6483(4) 0.5472(2) 0.8430(2) 0.0651(7) Uani 1 1 d . . . . .
H18 H 0.6715 0.4693 0.8687 0.078 Uiso 1 1 calc R U . . .
C19 C 0.5933(4) 0.5786(2) 0.7547(2) 0.0664(8) Uani 1 1 d . . . . .
H19 H 0.5811 0.5225 0.7192 0.080 Uiso 1 1 calc R U . . .
C20 C 0.5567(3) 0.6940(2) 0.71958(18) 0.0534(6) Uani 1 1 d . . . . .
C21 C 0.5796(3) 0.7788(2) 0.76799(17) 0.0452(6) Uani 1 1 d . . . . .
H21 H 0.5529 0.8565 0.7426 0.054 Uiso 1 1 calc R U . . .
C22 C 0.6425(3) 0.74826(18) 0.85460(16) 0.0394(5) Uani 1 1 d . . . . .
C23 C 0.6803(3) 0.82781(17) 0.91168(15) 0.0362(5) Uani 1 1 d . . . . .
C24 C 0.6809(3) 0.78755(18) 1.01755(16) 0.0386(5) Uani 1 1 d . . . . .
C25 C 0.6411(3) 0.67219(19) 1.06592(17) 0.0477(6) Uani 1 1 d . . . . .
H25 H 0.5210 0.6799 1.0846 0.057 Uiso 1 1 calc R U . . .
C26 C 0.6935(3) 0.62109(18) 1.16392(17) 0.0442(6) Uani 1 1 d . . . . .
C27 C 0.5883(3) 0.6498(2) 1.26273(18) 0.0532(6) Uani 1 1 d . . . . .
H27 H 0.4878 0.7016 1.2668 0.064 Uiso 1 1 calc R U . . .
C28 C 0.6275(3) 0.6042(2) 1.35504(19) 0.0583(7) Uani 1 1 d . . . . .
H28 H 0.5547 0.6255 1.4208 0.070 Uiso 1 1 calc R U . . .
C29 C 0.7727(4) 0.5279(2) 1.3502(2) 0.0562(7) Uani 1 1 d . . . . .
C30 C 0.8818(4) 0.4971(2) 1.2540(2) 0.0697(8) Uani 1 1 d . . . . .
H30 H 0.9818 0.4451 1.2513 0.084 Uiso 1 1 calc R U . . .
C31 C 0.8424(3) 0.5438(2) 1.1608(2) 0.0616(7) Uani 1 1 d . . . . .
H31 H 0.9167 0.5232 1.0951 0.074 Uiso 1 1 calc R U . . .
Cl1 Cl 0.47416(11) 0.73555(6) 0.61284(6) 0.0870(3) Uani 1 1 d . . . . .
Cl2 Cl 0.82084(12) 0.46896(7) 1.46787(6) 0.0978(3) Uani 1 1 d . . . . .
N1 N 0.7302(2) 0.96784(14) 0.98177(12) 0.0364(4) Uani 1 1 d . . . . .
O1 O 0.6747(2) 1.12825(13) 0.80015(12) 0.0517(4) Uani 1 1 d . . . . .
O2 O 0.8809(2) 0.86720(15) 0.38814(12) 0.0689(5) Uani 1 1 d . . . . .
O3 O 0.7202(2) 0.59311(12) 0.98424(12) 0.0580(5) Uani 1 1 d . . . . .
S1 S 0.74028(8) 0.89349(5) 1.17632(4) 0.04823(19) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.373(3) . ?
C1 C6 1.395(3) . ?
C1 N1 1.420(2) . ?
C2 C3 1.392(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9300 . ?
C6 S1 1.747(2) . ?
C7 C24 1.368(3) . ?
C7 N1 1.380(3) . ?
C7 S1 1.728(2) . ?
C8 C23 1.402(3) . ?
C8 N1 1.410(2) . ?
C8 C9 1.463(3) . ?
C9 O1 1.226(2) . ?
C9 C10 1.481(3) . ?
C10 C11 1.380(3) . ?
C10 C16 1.397(3) . ?
C11 C12 1.391(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C13 O2 1.363(3) . ?
C13 C15 1.387(3) . ?
C14 O2 1.416(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.361(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.377(3) . ?
C17 O3 1.377(3) . ?
C17 C22 1.403(3) . ?
C18 C19 1.370(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(3) . ?
C20 Cl1 1.739(2) . ?
C21 C22 1.389(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.472(3) . ?
C23 C24 1.407(3) . ?
C24 C25 1.491(3) . ?
C25 O3 1.445(3) . ?
C25 C26 1.501(3) . ?
C25 H25 0.9800 . ?
C26 C27 1.376(3) . ?
C26 C31 1.386(3) . ?
C27 C28 1.367(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.353(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.366(4) . ?
C29 Cl2 1.737(2) . ?
C30 C31 1.381(3) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.63(19) . . ?
C2 C1 N1 129.95(19) . . ?
C6 C1 N1 110.42(18) . . ?
C1 C2 C3 118.4(2) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 121.7(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 118.3(2) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C5 C6 C1 121.2(2) . . ?
C5 C6 S1 125.11(18) . . ?
C1 C6 S1 113.65(16) . . ?
C24 C7 N1 109.53(17) . . ?
C24 C7 S1 137.00(16) . . ?
N1 C7 S1 113.45(14) . . ?
C23 C8 N1 106.07(16) . . ?
C23 C8 C9 131.66(18) . . ?
N1 C8 C9 121.99(18) . . ?
O1 C9 C8 121.39(19) . . ?
O1 C9 C10 119.67(19) . . ?
C8 C9 C10 118.91(19) . . ?
C11 C10 C16 118.24(19) . . ?
C11 C10 C9 122.95(19) . . ?
C16 C10 C9 118.8(2) . . ?
C10 C11 C12 121.4(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 119.1(2) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
O2 C13 C12 124.4(2) . . ?
O2 C13 C15 115.8(2) . . ?
C12 C13 C15 119.8(2) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 120.7(2) . . ?
C16 C15 H15 119.7 . . ?
C13 C15 H15 119.7 . . ?
C15 C16 C10 120.7(2) . . ?
C15 C16 H16 119.7 . . ?
C10 C16 H16 119.7 . . ?
C18 C17 O3 117.2(2) . . ?
C18 C17 C22 121.3(2) . . ?
O3 C17 C22 121.50(19) . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 118.9(2) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 C21 121.9(2) . . ?
C19 C20 Cl1 119.29(18) . . ?
C21 C20 Cl1 118.81(19) . . ?
C20 C21 C22 120.1(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 117.33(19) . . ?
C21 C22 C23 126.48(19) . . ?
C17 C22 C23 116.17(19) . . ?
C8 C23 C24 108.74(17) . . ?
C8 C23 C22 135.57(18) . . ?
C24 C23 C22 115.68(18) . . ?
C7 C24 C23 107.24(18) . . ?
C7 C24 C25 132.51(19) . . ?
C23 C24 C25 120.15(18) . . ?
O3 C25 C24 107.14(17) . . ?
O3 C25 C26 108.91(18) . . ?
C24 C25 C26 115.96(18) . . ?
O3 C25 H25 108.2 . . ?
C24 C25 H25 108.2 . . ?
C26 C25 H25 108.2 . . ?
C27 C26 C31 117.6(2) . . ?
C27 C26 C25 119.1(2) . . ?
C31 C26 C25 123.4(2) . . ?
C28 C27 C26 121.8(2) . . ?
C28 C27 H27 119.1 . . ?
C26 C27 H27 119.1 . . ?
C29 C28 C27 119.6(2) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C28 C29 C30 120.8(2) . . ?
C28 C29 Cl2 119.4(2) . . ?
C30 C29 Cl2 119.7(2) . . ?
C29 C30 C31 119.4(2) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C30 C31 C26 120.7(2) . . ?
C30 C31 H31 119.6 . . ?
C26 C31 H31 119.6 . . ?
C7 N1 C8 108.37(16) . . ?
C7 N1 C1 112.94(16) . . ?
C8 N1 C1 138.17(17) . . ?
C13 O2 C14 117.55(19) . . ?
C17 O3 C25 112.36(17) . . ?
C7 S1 C6 89.42(10) . . ?

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_3r
_database_code_depnum_ccdc_archive 'CCDC 1546833'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H22 Br Cl N2 O4 S'
_chemical_formula_sum            'C31 H22 Br Cl N2 O4 S'
_chemical_formula_weight         633.92

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.5910(12)
_cell_length_b                   13.1205(13)
_cell_length_c                   20.4645(18)
_cell_angle_alpha                90
_cell_angle_beta                 118.012(5)
_cell_angle_gamma                90
_cell_volume                     2747.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9881
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.09

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    1.710
_shelx_estimated_absorpt_T_min   0.665
_shelx_estimated_absorpt_T_max   0.684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_T_max  0.663
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38256
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.255
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5396
_reflns_number_gt                4433
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+1.0726P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5396
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.23285(3) 1.13684(2) 0.36100(2) 0.07105(13) Uani 1 1 d . . . . .
Cl1 Cl 0.52717(10) 1.39338(6) 0.55132(7) 0.1050(4) Uani 1 1 d . . . . .
S1 S 0.54226(5) 0.65383(4) 0.67584(3) 0.04229(15) Uani 1 1 d . . . . .
O1 O 0.28690(13) 1.00447(11) 0.65768(8) 0.0406(3) Uani 1 1 d . . . . .
O2 O 0.21842(18) 0.67782(13) 0.47523(9) 0.0568(4) Uani 1 1 d . . . . .
O3 O 0.28231(17) 0.57946(12) 0.57038(9) 0.0553(4) Uani 1 1 d . . . . .
O4 O 0.07510(13) 0.82345(11) 0.51773(8) 0.0384(3) Uani 1 1 d . . . . .
N1 N 0.45558(15) 0.83411(12) 0.69789(8) 0.0307(4) Uani 1 1 d . . . . .
N2 N 0.26572(16) 0.66328(13) 0.54156(10) 0.0379(4) Uani 1 1 d . . . . .
C1 C 0.5464(2) 1.11794(16) 0.63615(13) 0.0437(5) Uani 1 1 d . . . . .
H1 H 0.6100 1.0689 0.6609 0.052 Uiso 1 1 calc R U . . .
C2 C 0.5805(2) 1.20894(18) 0.61594(15) 0.0542(6) Uani 1 1 d . . . . .
H2 H 0.6672 1.2220 0.6281 0.065 Uiso 1 1 calc R U . . .
C3 C 0.4855(3) 1.27991(17) 0.57782(15) 0.0530(6) Uani 1 1 d . . . . .
C4 C 0.3570(2) 1.26263(18) 0.55967(14) 0.0509(6) Uani 1 1 d . . . . .
H4 H 0.2934 1.3109 0.5329 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3236(2) 1.17317(17) 0.58154(13) 0.0419(5) Uani 1 1 d . . . . .
H5 H 0.2372 1.1620 0.5707 0.050 Uiso 1 1 calc R U . . .
C6 C 0.41751(19) 1.09921(14) 0.61968(11) 0.0328(4) Uani 1 1 d . . . . .
C7 C 0.37475(18) 1.00393(14) 0.64095(10) 0.0310(4) Uani 1 1 d . . . . .
C8 C 0.43768(17) 0.90324(14) 0.63661(10) 0.0289(4) Uani 1 1 d . . . . .
H8 H 0.5231 0.9174 0.6396 0.035 Uiso 1 1 calc R U . . .
C9 C 0.59043(18) 0.82484(15) 0.75150(10) 0.0331(4) Uani 1 1 d . . . . .
C10 C 0.6608(2) 0.90036(17) 0.80132(12) 0.0451(5) Uani 1 1 d . . . . .
H10 H 0.6196 0.9591 0.8053 0.054 Uiso 1 1 calc R U . . .
C11 C 0.7938(2) 0.88677(19) 0.84524(13) 0.0528(6) Uani 1 1 d . . . . .
H11 H 0.8428 0.9368 0.8791 0.063 Uiso 1 1 calc R U . . .
C12 C 0.8539(2) 0.7996(2) 0.83910(13) 0.0518(6) Uani 1 1 d . . . . .
H12 H 0.9436 0.7920 0.8686 0.062 Uiso 1 1 calc R U . . .
C13 C 0.7840(2) 0.72303(18) 0.78996(12) 0.0442(5) Uani 1 1 d . . . . .
H13 H 0.8254 0.6640 0.7867 0.053 Uiso 1 1 calc R U . . .
C14 C 0.65049(19) 0.73644(15) 0.74560(11) 0.0346(4) Uani 1 1 d . . . . .
C15 C 0.40432(18) 0.73351(14) 0.66911(10) 0.0319(4) Uani 1 1 d . . . . .
H15 H 0.3664 0.7028 0.6983 0.038 Uiso 1 1 calc R U . . .
C16 C 0.1224(2) 0.70759(18) 0.68632(12) 0.0456(5) Uani 1 1 d . . . . .
H16 H 0.1827 0.7519 0.7210 0.055 Uiso 1 1 calc R U . . .
C17 C 0.0571(3) 0.6381(2) 0.70789(13) 0.0537(6) Uani 1 1 d . . . . .
H17 H 0.0756 0.6354 0.7573 0.064 Uiso 1 1 calc R U . . .
C18 C -0.0354(2) 0.57238(18) 0.65735(13) 0.0469(5) Uani 1 1 d . . . . .
C19 C -0.1079(3) 0.4974(3) 0.68023(18) 0.0760(9) Uani 1 1 d . . . . .
H19A H -0.0543 0.4385 0.7018 0.114 Uiso 1 1 calc R U . . .
H19B H -0.1872 0.4773 0.6376 0.114 Uiso 1 1 calc R U . . .
H19C H -0.1287 0.5286 0.7159 0.114 Uiso 1 1 calc R U . . .
C20 C -0.0588(2) 0.57784(17) 0.58465(12) 0.0429(5) Uani 1 1 d . . . . .
H20 H -0.1204 0.5345 0.5497 0.052 Uiso 1 1 calc R U . . .
C21 C 0.0067(2) 0.64582(16) 0.56269(11) 0.0389(5) Uani 1 1 d . . . . .
H21 H -0.0110 0.6475 0.5134 0.047 Uiso 1 1 calc R U . . .
C22 C 0.09865(19) 0.71177(15) 0.61325(11) 0.0334(4) Uani 1 1 d . . . . .
C23 C 0.16776(18) 0.78965(15) 0.59029(11) 0.0318(4) Uani 1 1 d . . . . .
H23 H 0.1886 0.8479 0.6239 0.038 Uiso 1 1 calc R U . . .
C24 C 0.29677(18) 0.75531(14) 0.59058(10) 0.0300(4) Uani 1 1 d . . . . .
C25 C 0.35209(17) 0.84275(14) 0.56386(10) 0.0283(4) Uani 1 1 d . . . . .
H25 H 0.4098 0.8137 0.5458 0.034 Uiso 1 1 calc R U . . .
C26 C 0.24824(18) 0.90500(15) 0.50245(10) 0.0297(4) Uani 1 1 d . . . . .
C27 C 0.2813(2) 0.97673(16) 0.46406(11) 0.0359(4) Uani 1 1 d . . . . .
H27 H 0.3682 0.9851 0.4750 0.043 Uiso 1 1 calc R U . . .
C28 C 0.1859(2) 1.03553(16) 0.40982(11) 0.0382(5) Uani 1 1 d . . . . .
C29 C 0.0559(2) 1.02314(17) 0.39154(11) 0.0404(5) Uani 1 1 d . . . . .
H29 H -0.0079 1.0629 0.3546 0.048 Uiso 1 1 calc R U . . .
C30 C 0.02176(19) 0.95169(17) 0.42833(11) 0.0378(5) Uani 1 1 d . . . . .
H30 H -0.0657 0.9421 0.4158 0.045 Uiso 1 1 calc R U . . .
C31 C 0.11760(18) 0.89379(15) 0.48417(10) 0.0324(4) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C28 1.890(2) . ?
Cl1 C3 1.729(2) . ?
S1 C14 1.762(2) . ?
S1 C15 1.860(2) . ?
O1 C7 1.217(2) . ?
O2 N2 1.217(2) . ?
O3 N2 1.220(2) . ?
O4 C31 1.372(2) . ?
O4 C23 1.434(2) . ?
N1 C9 1.432(2) . ?
N1 C15 1.454(2) . ?
N1 C8 1.481(2) . ?
N2 C24 1.502(2) . ?
C1 C2 1.381(3) . ?
C1 C6 1.390(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(4) . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.483(3) . ?
C7 C8 1.532(3) . ?
C8 C25 1.563(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.380(3) . ?
C9 C14 1.387(3) . ?
C10 C11 1.384(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9300 . ?
C15 C24 1.529(3) . ?
C15 H15 0.9800 . ?
C16 C17 1.383(3) . ?
C16 C22 1.389(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9300 . ?
C18 C20 1.383(3) . ?
C18 C19 1.505(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.376(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.386(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.503(3) . ?
C23 C24 1.559(3) . ?
C23 H23 0.9800 . ?
C24 C25 1.535(3) . ?
C25 C26 1.508(3) . ?
C25 H25 0.9800 . ?
C26 C31 1.386(3) . ?
C26 C27 1.390(3) . ?
C27 C28 1.377(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.381(3) . ?
C29 C30 1.372(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.387(3) . ?
C30 H30 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 S1 C15 88.53(9) . . ?
C31 O4 C23 117.12(14) . . ?
C9 N1 C15 108.94(15) . . ?
C9 N1 C8 111.66(15) . . ?
C15 N1 C8 110.17(14) . . ?
O2 N2 O3 124.54(18) . . ?
O2 N2 C24 117.40(17) . . ?
O3 N2 C24 117.91(17) . . ?
C2 C1 C6 120.5(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 Cl1 119.7(2) . . ?
C4 C3 Cl1 118.95(19) . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.77(19) . . ?
C1 C6 C7 123.16(18) . . ?
C5 C6 C7 118.08(18) . . ?
O1 C7 C6 121.10(17) . . ?
O1 C7 C8 120.36(17) . . ?
C6 C7 C8 118.42(17) . . ?
N1 C8 C7 111.11(16) . . ?
N1 C8 C25 105.63(14) . . ?
C7 C8 C25 112.74(14) . . ?
N1 C8 H8 109.1 . . ?
C7 C8 H8 109.1 . . ?
C25 C8 H8 109.1 . . ?
C10 C9 C14 121.22(19) . . ?
C10 C9 N1 123.94(19) . . ?
C14 C9 N1 114.60(17) . . ?
C9 C10 C11 118.6(2) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.4(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C14 118.4(2) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C9 C14 C13 119.97(19) . . ?
C9 C14 S1 112.93(14) . . ?
C13 C14 S1 127.03(17) . . ?
N1 C15 C24 103.43(14) . . ?
N1 C15 S1 107.86(13) . . ?
C24 C15 S1 115.54(14) . . ?
N1 C15 H15 109.9 . . ?
C24 C15 H15 109.9 . . ?
S1 C15 H15 109.9 . . ?
C17 C16 C22 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C22 C16 H16 119.7 . . ?
C16 C17 C18 121.3(2) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C20 C18 C17 117.6(2) . . ?
C20 C18 C19 120.8(2) . . ?
C17 C18 C19 121.6(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C18 121.7(2) . . ?
C21 C20 H20 119.2 . . ?
C18 C20 H20 119.2 . . ?
C20 C21 C22 120.6(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C16 118.25(19) . . ?
C21 C22 C23 121.80(18) . . ?
C16 C22 C23 119.89(18) . . ?
O4 C23 C22 106.50(15) . . ?
O4 C23 C24 110.10(15) . . ?
C22 C23 C24 116.96(16) . . ?
O4 C23 H23 107.6 . . ?
C22 C23 H23 107.6 . . ?
C24 C23 H23 107.6 . . ?
N2 C24 C15 111.91(15) . . ?
N2 C24 C25 111.85(16) . . ?
C15 C24 C25 104.10(15) . . ?
N2 C24 C23 107.54(15) . . ?
C15 C24 C23 111.42(16) . . ?
C25 C24 C23 110.06(15) . . ?
C26 C25 C24 113.47(15) . . ?
C26 C25 C8 114.83(15) . . ?
C24 C25 C8 102.98(14) . . ?
C26 C25 H25 108.4 . . ?
C24 C25 H25 108.4 . . ?
C8 C25 H25 108.4 . . ?
C31 C26 C27 118.39(17) . . ?
C31 C26 C25 120.69(17) . . ?
C27 C26 C25 120.90(17) . . ?
C28 C27 C26 120.30(19) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C29 120.88(19) . . ?
C27 C28 Br1 119.90(16) . . ?
C29 C28 Br1 119.20(15) . . ?
C30 C29 C28 119.42(18) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C29 C30 C31 120.02(19) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
O4 C31 C26 122.65(16) . . ?
O4 C31 C30 116.34(17) . . ?
C26 C31 C30 120.97(18) . . ?

_refine_diff_density_max         0.446
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_5c
_database_code_depnum_ccdc_archive 'CCDC 1546835'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H22 Cl N O3 S'
_chemical_formula_sum            'C32 H22 Cl N O3 S'
_chemical_formula_weight         536.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   12.9531(11)
_cell_length_b                   13.3809(11)
_cell_length_c                   15.6390(14)
_cell_angle_alpha                90
_cell_angle_beta                 106.449(3)
_cell_angle_gamma                90
_cell_volume                     2599.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6616
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      22.75

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.263
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35301
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.639
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5098
_reflns_number_gt                2957
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1947P)²+0.7066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5098
_refine_ls_number_parameters     345
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.1577
_refine_ls_R_factor_gt           0.0923
_refine_ls_wR_factor_ref         0.3078
_refine_ls_wR_factor_gt          0.2705
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7238(4) 0.1728(4) 0.0804(3) 0.0499(13) Uani 1 1 d . . . . .
H1 H 0.7519 0.2233 0.1211 0.060 Uiso 1 1 calc R U . . .
C2 C 0.7902(5) 0.0979(4) 0.0672(4) 0.0632(15) Uani 1 1 d . . . . .
H2 H 0.8624 0.0970 0.0997 0.076 Uiso 1 1 calc R U . . .
C3 C 0.7483(6) 0.0226(4) 0.0045(4) 0.0710(18) Uani 1 1 d . . . . .
C4 C 0.7647(7) -0.1123(5) -0.0858(5) 0.1083(16) Uani 1 1 d . U . . .
H4A H 0.6976 -0.1360 -0.0789 0.163 Uiso 1 1 calc R U . . .
H4B H 0.8105 -0.1681 -0.0876 0.163 Uiso 1 1 calc R U . . .
H4C H 0.7516 -0.0750 -0.1402 0.163 Uiso 1 1 calc R U . . .
C5 C 0.6423(6) 0.0224(5) -0.0399(4) 0.0746(19) Uani 1 1 d . . . . .
H5 H 0.6146 -0.0280 -0.0809 0.090 Uiso 1 1 calc R U . . .
C6 C 0.5756(5) 0.0950(4) -0.0252(4) 0.0639(16) Uani 1 1 d . . . . .
H6 H 0.5024 0.0923 -0.0548 0.077 Uiso 1 1 calc R U . . .
C7 C 0.6159(4) 0.1740(4) 0.0339(3) 0.0456(12) Uani 1 1 d . . . . .
C8 C 0.5421(4) 0.2572(4) 0.0403(3) 0.0486(12) Uani 1 1 d . . . . .
C9 C 0.5888(3) 0.3559(3) 0.0559(3) 0.0379(11) Uani 1 1 d . . . . .
C10 C 0.6133(3) 0.5144(3) 0.1094(3) 0.0384(11) Uani 1 1 d . . . . .
C11 C 0.4904(4) 0.5265(4) 0.2016(3) 0.0513(13) Uani 1 1 d . . . . .
C12 C 0.4262(4) 0.5475(5) 0.2574(4) 0.0651(16) Uani 1 1 d . . . . .
H12 H 0.4286 0.6103 0.2834 0.078 Uiso 1 1 calc R U . . .
C13 C 0.3595(5) 0.4745(6) 0.2738(4) 0.0749(18) Uani 1 1 d . . . . .
H13 H 0.3149 0.4887 0.3095 0.090 Uiso 1 1 calc R U . . .
C14 C 0.3582(4) 0.3807(5) 0.2376(4) 0.0719(18) Uani 1 1 d . . . . .
H14 H 0.3145 0.3315 0.2510 0.086 Uiso 1 1 calc R U . . .
C15 C 0.4206(4) 0.3581(4) 0.1818(4) 0.0584(14) Uani 1 1 d . . . . .
H15 H 0.4184 0.2947 0.1570 0.070 Uiso 1 1 calc R U . . .
C16 C 0.4862(3) 0.4314(4) 0.1635(3) 0.0467(12) Uani 1 1 d . . . . .
C17 C 0.8225(3) 0.4286(3) -0.0314(3) 0.0378(11) Uani 1 1 d . . . . .
C18 C 0.8919(4) 0.4029(4) -0.0811(4) 0.0524(13) Uani 1 1 d . . . . .
H18 H 0.9530 0.4413 -0.0769 0.063 Uiso 1 1 calc R U . . .
C19 C 0.8709(4) 0.3211(4) -0.1367(3) 0.0520(13) Uani 1 1 d . . . . .
H19 H 0.9186 0.3020 -0.1683 0.062 Uiso 1 1 calc R U . . .
C20 C 0.7786(4) 0.2686(3) -0.1443(3) 0.0421(11) Uani 1 1 d . . . . .
C21 C 0.7075(4) 0.2940(4) -0.0963(3) 0.0426(11) Uani 1 1 d . . . . .
H21 H 0.6437 0.2585 -0.1046 0.051 Uiso 1 1 calc R U . . .
C22 C 0.7312(3) 0.3718(3) -0.0362(3) 0.0337(10) Uani 1 1 d . . . . .
C23 C 0.6674(3) 0.4029(3) 0.0242(3) 0.0382(11) Uani 1 1 d . . . . .
C24 C 0.6843(3) 0.5005(3) 0.0599(3) 0.0383(11) Uani 1 1 d . . . . .
C25 C 0.7663(3) 0.5691(3) 0.0413(3) 0.0422(11) Uani 1 1 d . . . . .
H25 H 0.7332 0.6093 -0.0118 0.051 Uiso 1 1 calc R U . . .
C26 C 0.8174(4) 0.6365(4) 0.1185(4) 0.0624(8) Uani 1 1 d . U . . .
C27 C 0.8165(4) 0.7390(4) 0.1091(4) 0.0642(8) Uani 1 1 d . U . . .
H27 H 0.7827 0.7682 0.0543 0.077 Uiso 1 1 calc R U . . .
C28 C 0.8665(4) 0.7989(5) 0.1822(4) 0.0662(8) Uani 1 1 d . U . . .
H28 H 0.8659 0.8678 0.1746 0.079 Uiso 1 1 calc R U . . .
C29 C 0.9143(4) 0.7620(4) 0.2610(4) 0.0665(8) Uani 1 1 d . U . . .
C30 C 0.9663(7) 0.8250(7) 0.3423(7) 0.146(4) Uani 1 1 d . . . . .
H30A H 1.0403 0.8369 0.3454 0.219 Uiso 1 1 calc R U . . .
H30B H 0.9623 0.7904 0.3951 0.219 Uiso 1 1 calc R U . . .
H30C H 0.9291 0.8877 0.3381 0.219 Uiso 1 1 calc R U . . .
C31 C 0.9161(4) 0.6596(4) 0.2708(4) 0.0665(8) Uani 1 1 d . U . . .
H31 H 0.9500 0.6320 0.3262 0.080 Uiso 1 1 calc R U . . .
C32 C 0.8690(4) 0.5972(4) 0.2008(4) 0.0645(8) Uani 1 1 d . U . . .
H32 H 0.8720 0.5283 0.2092 0.077 Uiso 1 1 calc R U . . .
Cl1 Cl 0.74915(12) 0.16523(11) -0.21572(9) 0.0658(5) Uani 1 1 d . . . . .
N1 N 0.5547(3) 0.4284(3) 0.1068(2) 0.0397(9) Uani 1 1 d . . . . .
O1 O 0.8170(4) -0.0479(4) -0.0106(3) 0.1003(14) Uani 1 1 d . U . . .
O2 O 0.4465(3) 0.2414(3) 0.0315(3) 0.0724(12) Uani 1 1 d . . . . .
O3 O 0.8521(2) 0.5084(2) 0.0259(2) 0.0507(9) Uani 1 1 d . . . . .
S1 S 0.58190(10) 0.60662(10) 0.17451(9) 0.0557(5) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.373(7) . ?
C1 C7 1.381(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.403(8) . ?
C2 H2 0.9300 . ?
C3 C5 1.351(9) . ?
C3 O1 1.362(7) . ?
C4 O1 1.460(8) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.363(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.404(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.490(7) . ?
C8 O2 1.224(5) . ?
C8 C9 1.444(6) . ?
C9 C23 1.402(6) . ?
C9 N1 1.403(5) . ?
C10 C24 1.372(6) . ?
C10 N1 1.373(6) . ?
C10 S1 1.720(5) . ?
C11 C12 1.394(7) . ?
C11 C16 1.400(7) . ?
C11 S1 1.737(5) . ?
C12 C13 1.376(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(7) . ?
C15 H15 0.9300 . ?
C16 N1 1.422(6) . ?
C17 O3 1.377(5) . ?
C17 C18 1.389(6) . ?
C17 C22 1.389(6) . ?
C18 C19 1.376(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.363(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.385(6) . ?
C20 Cl1 1.751(5) . ?
C21 C22 1.377(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.479(6) . ?
C23 C24 1.413(6) . ?
C24 C25 1.493(6) . ?
C25 O3 1.451(5) . ?
C25 C26 1.502(7) . ?
C25 H25 0.9800 . ?
C26 C32 1.376(8) . ?
C26 C27 1.380(7) . ?
C27 C28 1.396(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.309(8) . ?
C28 H28 0.9300 . ?
C29 C31 1.378(8) . ?
C29 C30 1.515(9) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.374(7) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 120.9(5) . . ?
C2 C1 H1 119.6 . . ?
C7 C1 H1 119.6 . . ?
C1 C2 C3 119.6(6) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C5 C3 O1 121.9(6) . . ?
C5 C3 C2 119.7(6) . . ?
O1 C3 C2 118.4(7) . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 120.9(5) . . ?
C3 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 120.8(6) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C1 C7 C6 118.0(5) . . ?
C1 C7 C8 123.1(4) . . ?
C6 C7 C8 118.8(5) . . ?
O2 C8 C9 122.6(5) . . ?
O2 C8 C7 120.7(5) . . ?
C9 C8 C7 116.7(4) . . ?
C23 C9 N1 105.5(4) . . ?
C23 C9 C8 131.5(4) . . ?
N1 C9 C8 122.9(4) . . ?
C24 C10 N1 108.8(4) . . ?
C24 C10 S1 137.7(4) . . ?
N1 C10 S1 113.4(3) . . ?
C12 C11 C16 119.4(5) . . ?
C12 C11 S1 126.7(5) . . ?
C16 C11 S1 113.9(3) . . ?
C13 C12 C11 119.4(6) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 121.3(6) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C16 118.7(6) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C11 120.7(4) . . ?
C15 C16 N1 129.7(5) . . ?
C11 C16 N1 109.6(4) . . ?
O3 C17 C18 116.8(4) . . ?
O3 C17 C22 122.4(4) . . ?
C18 C17 C22 120.7(4) . . ?
C19 C18 C17 120.4(4) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 118.5(4) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C21 121.8(4) . . ?
C19 C20 Cl1 119.4(4) . . ?
C21 C20 Cl1 118.8(4) . . ?
C22 C21 C20 120.1(4) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C17 118.2(4) . . ?
C21 C22 C23 126.2(4) . . ?
C17 C22 C23 115.6(4) . . ?
C9 C23 C24 108.7(4) . . ?
C9 C23 C22 133.8(4) . . ?
C24 C23 C22 117.4(4) . . ?
C10 C24 C23 107.2(4) . . ?
C10 C24 C25 130.8(4) . . ?
C23 C24 C25 122.0(4) . . ?
O3 C25 C24 108.0(4) . . ?
O3 C25 C26 106.5(4) . . ?
C24 C25 C26 112.9(4) . . ?
O3 C25 H25 109.8 . . ?
C24 C25 H25 109.8 . . ?
C26 C25 H25 109.8 . . ?
C32 C26 C27 117.8(5) . . ?
C32 C26 C25 120.6(5) . . ?
C27 C26 C25 121.5(5) . . ?
C26 C27 C28 119.7(6) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C29 C28 C27 122.8(6) . . ?
C29 C28 H28 118.6 . . ?
C27 C28 H28 118.6 . . ?
C28 C29 C31 117.9(6) . . ?
C28 C29 C30 124.0(7) . . ?
C31 C29 C30 118.1(7) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C29 121.8(6) . . ?
C32 C31 H31 119.1 . . ?
C29 C31 H31 119.1 . . ?
C31 C32 C26 120.1(6) . . ?
C31 C32 H32 120.0 . . ?
C26 C32 H32 120.0 . . ?
C10 N1 C9 109.6(3) . . ?
C10 N1 C16 113.3(4) . . ?
C9 N1 C16 136.5(4) . . ?
C3 O1 C4 111.8(6) . . ?
C17 O3 C25 117.2(3) . . ?
C10 S1 C11 89.6(2) . . ?

_refine_diff_density_max         1.692
_refine_diff_density_min         -1.169
_refine_diff_density_rms         0.134

####################################################################### 
# 
# 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_4d
_database_code_depnum_ccdc_archive 'CCDC 1546834'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 Cl2 N2 O5 S'
_chemical_formula_sum            'C26 H20 Cl2 N2 O5 S'
_chemical_formula_weight         543.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   14.6578(7)
_cell_length_b                   10.9282(5)
_cell_length_c                   16.4917(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.7536(15)
_cell_angle_gamma                90
_cell_volume                     2453.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9989
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.27

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.391
_shelx_estimated_absorpt_T_min   0.898
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21672
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.289
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4813
_reflns_number_gt                3781
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+0.5878P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4813
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.33869(15) 0.16410(18) 0.75555(12) 0.0406(5) Uani 1 1 d . . . . .
C2 C 0.38004(17) 0.1231(2) 0.69683(13) 0.0500(5) Uani 1 1 d . . . . .
H2 H 0.3516 0.0591 0.6587 0.060 Uiso 1 1 calc R U . . .
C3 C 0.46397(17) 0.1794(2) 0.69628(14) 0.0554(6) Uani 1 1 d . . . . .
H3 H 0.4927 0.1519 0.6579 0.067 Uiso 1 1 calc R U . . .
C4 C 0.50583(16) 0.2750(2) 0.75121(15) 0.0535(6) Uani 1 1 d . . . . .
H4 H 0.5611 0.3133 0.7480 0.064 Uiso 1 1 calc R U . . .
C5 C 0.46710(14) 0.3155(2) 0.81148(13) 0.0452(5) Uani 1 1 d . . . . .
H5 H 0.4959 0.3800 0.8490 0.054 Uiso 1 1 calc R U . . .
C6 C 0.38460(14) 0.25738(17) 0.81436(12) 0.0367(4) Uani 1 1 d . . . . .
C7 C 0.26834(14) 0.19117(16) 0.87202(12) 0.0372(4) Uani 1 1 d . . . . .
H7 H 0.3024 0.1311 0.9173 0.045 Uiso 1 1 calc R U . . .
C8 C 0.28974(13) 0.40928(15) 0.85918(11) 0.0308(4) Uani 1 1 d . . . . .
H8 H 0.2857 0.4425 0.8028 0.037 Uiso 1 1 calc R U . . .
C9 C 0.34769(13) 0.49723(16) 0.93195(12) 0.0317(4) Uani 1 1 d . . . . .
C10 C 0.38215(19) 0.70669(19) 0.96541(15) 0.0579(6) Uani 1 1 d . . . . .
H10A H 0.4529 0.6981 0.9926 0.069 Uiso 1 1 calc R U . . .
H10B H 0.3547 0.7016 1.0105 0.069 Uiso 1 1 calc R U . . .
C11 C 0.3566(3) 0.8263(2) 0.91935(19) 0.0809(9) Uani 1 1 d . . . . .
H11A H 0.3817 0.8290 0.8732 0.121 Uiso 1 1 calc R U . . .
H11B H 0.3852 0.8915 0.9599 0.121 Uiso 1 1 calc R U . . .
H11C H 0.2865 0.8357 0.8952 0.121 Uiso 1 1 calc R U . . .
C12 C 0.18402(13) 0.38556(15) 0.85736(11) 0.0309(4) Uani 1 1 d . . . . .
H12 H 0.1389 0.3816 0.7963 0.037 Uiso 1 1 calc R U . . .
C13 C 0.14673(13) 0.48109(15) 0.90300(11) 0.0317(4) Uani 1 1 d . . . . .
C14 C 0.11655(14) 0.59450(16) 0.86473(13) 0.0386(4) Uani 1 1 d . . . . .
H14 H 0.1165 0.6108 0.8094 0.046 Uiso 1 1 calc R U . . .
C15 C 0.08674(14) 0.68277(17) 0.90907(14) 0.0421(5) Uani 1 1 d . . . . .
C16 C 0.08546(14) 0.66099(18) 0.99086(14) 0.0435(5) Uani 1 1 d . . . . .
H16 H 0.0658 0.7220 1.0202 0.052 Uiso 1 1 calc R U . . .
C17 C 0.11356(14) 0.54840(17) 1.02871(13) 0.0413(5) Uani 1 1 d . . . . .
H17 H 0.1122 0.5323 1.0836 0.050 Uiso 1 1 calc R U . . .
C18 C 0.14387(13) 0.45889(16) 0.98489(12) 0.0337(4) Uani 1 1 d . . . . .
C19 C 0.14387(15) 0.10412(18) 1.05813(14) 0.0436(5) Uani 1 1 d . . . . .
H19 H 0.0864 0.1500 1.0372 0.052 Uiso 1 1 calc R U . . .
C20 C 0.14503(15) -0.00415(18) 1.10181(14) 0.0444(5) Uani 1 1 d . . . . .
H20 H 0.0890 -0.0312 1.1101 0.053 Uiso 1 1 calc R U . . .
C21 C 0.23023(14) -0.07102(16) 1.13273(12) 0.0366(4) Uani 1 1 d . . . . .
C22 C 0.31421(14) -0.03170(18) 1.12163(13) 0.0417(5) Uani 1 1 d . . . . .
H22 H 0.3717 -0.0775 1.1432 0.050 Uiso 1 1 calc R U . . .
C23 C 0.31164(14) 0.07681(18) 1.07794(12) 0.0388(4) Uani 1 1 d . . . . .
H23 H 0.3682 0.1042 1.0706 0.047 Uiso 1 1 calc R U . . .
C24 C 0.22644(13) 0.14571(16) 1.04490(12) 0.0337(4) Uani 1 1 d . . . . .
C25 C 0.22544(14) 0.26489(16) 0.99850(12) 0.0333(4) Uani 1 1 d . . . . .
H25 H 0.2926 0.2971 1.0207 0.040 Uiso 1 1 calc R U . . .
C26 C 0.19092(13) 0.25742(16) 0.89733(11) 0.0329(4) Uani 1 1 d . . . . .
Cl1 Cl 0.05398(5) 0.82652(5) 0.86189(5) 0.0680(2) Uani 1 1 d . . . . .
Cl2 Cl 0.23250(4) -0.20568(5) 1.18973(4) 0.05287(17) Uani 1 1 d . . . . .
N1 N 0.33677(11) 0.28802(13) 0.87229(10) 0.0333(3) Uani 1 1 d . . . . .
N2 N 0.09238(13) 0.19507(15) 0.86341(11) 0.0431(4) Uani 1 1 d . . . . .
O1 O 0.39024(10) 0.46976(12) 1.00685(9) 0.0451(3) Uani 1 1 d . . . . .
O2 O 0.34148(10) 0.61006(11) 0.90081(9) 0.0425(3) Uani 1 1 d . . . . .
O3 O 0.16607(10) 0.34695(11) 1.02520(8) 0.0408(3) Uani 1 1 d . . . . .
O4 O 0.02162(11) 0.25490(15) 0.86030(11) 0.0618(4) Uani 1 1 d . . . . .
O5 O 0.08935(13) 0.08742(14) 0.84498(12) 0.0694(5) Uani 1 1 d . . . . .
S1 S 0.22796(4) 0.11615(5) 0.76370(4) 0.05220(17) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.393(3) . ?
C1 C6 1.396(3) . ?
C1 S1 1.757(2) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.419(2) . ?
C7 N1 1.457(2) . ?
C7 C26 1.529(3) . ?
C7 S1 1.8521(19) . ?
C7 H7 0.9800 . ?
C8 N1 1.472(2) . ?
C8 C9 1.526(2) . ?
C8 C12 1.560(2) . ?
C8 H8 0.9800 . ?
C9 O1 1.197(2) . ?
C9 O2 1.326(2) . ?
C10 O2 1.461(2) . ?
C10 C11 1.489(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.503(2) . ?
C12 C26 1.535(2) . ?
C12 H12 0.9800 . ?
C13 C14 1.387(2) . ?
C13 C18 1.388(3) . ?
C14 C15 1.376(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 Cl1 1.7397(19) . ?
C16 C17 1.372(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9300 . ?
C18 O3 1.373(2) . ?
C19 C20 1.382(3) . ?
C19 C24 1.384(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.379(3) . ?
C21 Cl2 1.7399(18) . ?
C22 C23 1.381(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.508(2) . ?
C25 O3 1.428(2) . ?
C25 C26 1.556(2) . ?
C25 H25 0.9800 . ?
C26 N2 1.505(2) . ?
N2 O4 1.211(2) . ?
N2 O5 1.212(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
C2 C1 C6 119.7(2) . . ?
C2 C1 S1 127.55(17) . . ?
C6 C1 S1 112.69(14) . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 118.3(2) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C1 120.94(18) . . ?
C5 C6 N1 124.88(18) . . ?
C1 C6 N1 114.14(17) . . ?
N1 C7 C26 103.59(14) . . ?
N1 C7 S1 107.34(12) . . ?
C26 C7 S1 117.95(13) . . ?
N1 C7 H7 109.2 . . ?
C26 C7 H7 109.2 . . ?
S1 C7 H7 109.2 . . ?
N1 C8 C9 110.94(14) . . ?
N1 C8 C12 105.12(13) . . ?
C9 C8 C12 112.28(14) . . ?
N1 C8 H8 109.5 . . ?
C9 C8 H8 109.5 . . ?
C12 C8 H8 109.5 . . ?
O1 C9 O2 124.58(17) . . ?
O1 C9 C8 125.35(16) . . ?
O2 C9 C8 110.04(15) . . ?
O2 C10 C11 107.77(19) . . ?
O2 C10 H10A 110.2 . . ?
C11 C10 H10A 110.2 . . ?
O2 C10 H10B 110.2 . . ?
C11 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C26 113.38(14) . . ?
C13 C12 C8 114.69(14) . . ?
C26 C12 C8 103.67(13) . . ?
C13 C12 H12 108.3 . . ?
C26 C12 H12 108.3 . . ?
C8 C12 H12 108.3 . . ?
C14 C13 C18 118.65(16) . . ?
C14 C13 C12 120.44(16) . . ?
C18 C13 C12 120.90(15) . . ?
C15 C14 C13 119.69(18) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 121.45(17) . . ?
C14 C15 Cl1 119.00(16) . . ?
C16 C15 Cl1 119.51(15) . . ?
C17 C16 C15 119.34(18) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 119.78(18) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
O3 C18 C17 116.20(16) . . ?
O3 C18 C13 122.67(16) . . ?
C17 C18 C13 121.06(17) . . ?
C20 C19 C24 121.39(18) . . ?
C20 C19 H19 119.3 . . ?
C24 C19 H19 119.3 . . ?
C21 C20 C19 118.91(18) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C20 C21 C22 121.29(17) . . ?
C20 C21 Cl2 118.93(15) . . ?
C22 C21 Cl2 119.74(15) . . ?
C21 C22 C23 118.94(18) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C22 C23 C24 121.22(17) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C19 C24 C23 118.24(17) . . ?
C19 C24 C25 121.27(16) . . ?
C23 C24 C25 120.45(16) . . ?
O3 C25 C24 106.17(14) . . ?
O3 C25 C26 111.74(14) . . ?
C24 C25 C26 115.91(15) . . ?
O3 C25 H25 107.6 . . ?
C24 C25 H25 107.6 . . ?
C26 C25 H25 107.6 . . ?
N2 C26 C7 113.04(15) . . ?
N2 C26 C12 110.61(15) . . ?
C7 C26 C12 104.61(14) . . ?
N2 C26 C25 107.95(14) . . ?
C7 C26 C25 109.77(14) . . ?
C12 C26 C25 110.86(14) . . ?
C6 N1 C7 109.75(14) . . ?
C6 N1 C8 115.78(14) . . ?
C7 N1 C8 111.65(14) . . ?
O4 N2 O5 124.22(18) . . ?
O4 N2 C26 117.41(16) . . ?
O5 N2 C26 118.27(18) . . ?
C9 O2 C10 116.02(15) . . ?
C18 O3 C25 118.21(13) . . ?
C1 S1 C7 88.15(9) . . ?

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_3e
_database_code_depnum_ccdc_archive 'CCDC 1546831'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H25 Br N2 O4 S'
_chemical_formula_sum            'C32 H25 Br N2 O4 S'
_chemical_formula_weight         613.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.643(2)
_cell_length_b                   13.163(3)
_cell_length_c                   20.446(4)
_cell_angle_alpha                90
_cell_angle_beta                 118.101(10)
_cell_angle_gamma                90
_cell_volume                     2764.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.10

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.604
_shelx_estimated_absorpt_T_min   0.662
_shelx_estimated_absorpt_T_max   0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_T_max  0.725
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25464
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.258
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5408
_reflns_number_gt                4218
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+0.7639P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5408
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.76879(3) 1.13722(2) 1.13969(2) 0.06693(12) Uani 1 1 d . . . . .
C1 C 0.34804(19) 0.73675(15) 0.75472(11) 0.0332(5) Uani 1 1 d . . . . .
C2 C 0.2151(2) 0.72300(18) 0.71045(12) 0.0440(5) Uani 1 1 d . . . . .
H2 H 0.1744 0.6639 0.7138 0.053 Uiso 1 1 calc R U . . .
C3 C 0.1446(2) 0.7994(2) 0.66119(13) 0.0515(6) Uani 1 1 d . . . . .
H3 H 0.0553 0.7915 0.6315 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2041(2) 0.88675(18) 0.65538(13) 0.0516(6) Uani 1 1 d . . . . .
H4 H 0.1549 0.9368 0.6217 0.062 Uiso 1 1 calc R U . . .
C5 C 0.3362(2) 0.90054(17) 0.69913(11) 0.0436(6) Uani 1 1 d . . . . .
H5 H 0.3766 0.9594 0.6952 0.052 Uiso 1 1 calc R U . . .
C6 C 0.40741(19) 0.82544(14) 0.74889(10) 0.0325(5) Uani 1 1 d . . . . .
C7 C 0.59399(18) 0.73462(14) 0.83063(11) 0.0303(4) Uani 1 1 d . . . . .
H7 H 0.6315 0.7045 0.8011 0.036 Uiso 1 1 calc R U . . .
C8 C 0.56158(18) 0.90426(13) 0.86339(10) 0.0277(4) Uani 1 1 d . . . . .
H8 H 0.4771 0.9193 0.8608 0.033 Uiso 1 1 calc R U . . .
C9 C 0.62544(18) 1.00396(14) 0.85903(10) 0.0298(4) Uani 1 1 d . . . . .
C10 C 0.5841(2) 1.09975(14) 0.88043(11) 0.0318(4) Uani 1 1 d . . . . .
C11 C 0.4568(2) 1.11904(16) 0.86520(13) 0.0422(5) Uani 1 1 d . . . . .
H11 H 0.3926 1.0703 0.8412 0.051 Uiso 1 1 calc R U . . .
C12 C 0.4254(2) 1.21102(17) 0.88577(15) 0.0522(6) Uani 1 1 d . . . . .
H12 H 0.3393 1.2240 0.8739 0.063 Uiso 1 1 calc R U . . .
C13 C 0.5186(3) 1.28359(16) 0.92331(15) 0.0503(6) Uani 1 1 d . . . . .
C14 C 0.4861(4) 1.3846(2) 0.9462(2) 0.0895(11) Uani 1 1 d . . . . .
H14A H 0.3945 1.3873 0.9308 0.134 Uiso 1 1 calc R U . . .
H14B H 0.5089 1.4388 0.9231 0.134 Uiso 1 1 calc R U . . .
H14C H 0.5341 1.3915 0.9991 0.134 Uiso 1 1 calc R U . . .
C15 C 0.6454(2) 1.26268(16) 0.93948(14) 0.0483(6) Uani 1 1 d . . . . .
H15 H 0.7100 1.3103 0.9655 0.058 Uiso 1 1 calc R U . . .
C16 C 0.6786(2) 1.17302(16) 0.91798(12) 0.0399(5) Uani 1 1 d . . . . .
H16 H 0.7645 1.1614 0.9286 0.048 Uiso 1 1 calc R U . . .
C17 C 0.64726(18) 0.84381(13) 0.93634(10) 0.0277(4) Uani 1 1 d . . . . .
H17 H 0.5901 0.8151 0.9546 0.033 Uiso 1 1 calc R U . . .
C18 C 0.75157(19) 0.90556(14) 0.99762(10) 0.0284(4) Uani 1 1 d . . . . .
C19 C 0.7194(2) 0.97744(15) 1.03650(11) 0.0340(5) Uani 1 1 d . . . . .
H19 H 0.6331 0.9856 1.0260 0.041 Uiso 1 1 calc R U . . .
C20 C 0.8144(2) 1.03606(16) 1.09000(11) 0.0367(5) Uani 1 1 d . . . . .
C21 C 0.9439(2) 1.02388(16) 1.10810(11) 0.0391(5) Uani 1 1 d . . . . .
H21 H 1.0076 1.0639 1.1447 0.047 Uiso 1 1 calc R U . . .
C22 C 0.9773(2) 0.95204(16) 1.07149(11) 0.0361(5) Uani 1 1 d . . . . .
H22 H 1.0643 0.9422 1.0838 0.043 Uiso 1 1 calc R U . . .
C23 C 0.88151(19) 0.89410(14) 1.01615(10) 0.0304(4) Uani 1 1 d . . . . .
C24 C 0.9907(2) 0.64658(15) 0.93701(12) 0.0374(5) Uani 1 1 d . . . . .
H24 H 1.0086 0.6483 0.9864 0.045 Uiso 1 1 calc R U . . .
C25 C 1.0558(2) 0.57885(16) 0.91487(12) 0.0411(5) Uani 1 1 d . . . . .
H25 H 1.1177 0.5359 0.9498 0.049 Uiso 1 1 calc R U . . .
C26 C 1.0311(2) 0.57316(17) 0.84194(13) 0.0446(5) Uani 1 1 d . . . . .
C27 C 1.1031(3) 0.4981(2) 0.81871(17) 0.0731(8) Uani 1 1 d . . . . .
H27A H 1.0482 0.4405 0.7955 0.110 Uiso 1 1 calc R U . . .
H27B H 1.1806 0.4761 0.8616 0.110 Uiso 1 1 calc R U . . .
H27C H 1.1261 0.5299 0.7843 0.110 Uiso 1 1 calc R U . . .
C28 C 0.9388(3) 0.63839(19) 0.79162(13) 0.0517(6) Uani 1 1 d . . . . .
H28 H 0.9199 0.6357 0.7421 0.062 Uiso 1 1 calc R U . . .
C29 C 0.8740(2) 0.70757(18) 0.81341(12) 0.0437(5) Uani 1 1 d . . . . .
H29 H 0.8132 0.7514 0.7786 0.052 Uiso 1 1 calc R U . . .
C30 C 0.89885(19) 0.71202(14) 0.88639(11) 0.0322(4) Uani 1 1 d . . . . .
C31 C 0.83027(18) 0.78998(14) 0.90993(10) 0.0308(4) Uani 1 1 d . . . . .
H31 H 0.8100 0.8484 0.8766 0.037 Uiso 1 1 calc R U . . .
C32 C 0.70163(19) 0.75630(14) 0.90922(10) 0.0292(4) Uani 1 1 d . . . . .
N1 N 0.54174(15) 0.83469(11) 0.80189(8) 0.0293(4) Uani 1 1 d . . . . .
N2 N 0.73194(16) 0.66416(12) 0.95821(10) 0.0365(4) Uani 1 1 d . . . . .
O1 O 0.71230(14) 1.00344(10) 0.84180(8) 0.0386(3) Uani 1 1 d . . . . .
O2 O 0.92328(13) 0.82295(10) 0.98270(8) 0.0371(3) Uani 1 1 d . . . . .
O3 O 0.77587(18) 0.67813(12) 1.02451(9) 0.0561(5) Uani 1 1 d . . . . .
O4 O 0.71710(16) 0.58069(11) 0.92950(9) 0.0542(4) Uani 1 1 d . . . . .
S1 S 0.45717(5) 0.65442(4) 0.82411(3) 0.04141(15) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C20 1.896(2) . ?
C1 C2 1.388(3) . ?
C1 C6 1.390(3) . ?
C1 S1 1.762(2) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.428(3) . ?
C7 N1 1.454(2) . ?
C7 C32 1.529(3) . ?
C7 S1 1.863(2) . ?
C7 H7 0.9800 . ?
C8 N1 1.483(2) . ?
C8 C9 1.532(3) . ?
C8 C17 1.566(3) . ?
C8 H8 0.9800 . ?
C9 O1 1.217(2) . ?
C9 C10 1.487(3) . ?
C10 C11 1.387(3) . ?
C10 C16 1.391(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C13 C15 1.380(3) . ?
C13 C14 1.515(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.507(3) . ?
C17 C32 1.538(3) . ?
C17 H17 0.9800 . ?
C18 C23 1.384(3) . ?
C18 C19 1.396(3) . ?
C19 C20 1.369(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(3) . ?
C21 C22 1.371(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(3) . ?
C22 H22 0.9300 . ?
C23 O2 1.376(2) . ?
C24 C25 1.377(3) . ?
C24 C30 1.383(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(3) . ?
C25 H25 0.9300 . ?
C26 C28 1.382(3) . ?
C26 C27 1.509(3) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.384(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.381(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.511(3) . ?
C31 O2 1.434(2) . ?
C31 C32 1.556(3) . ?
C31 H31 0.9800 . ?
C32 N2 1.505(2) . ?
N2 O3 1.216(2) . ?
N2 O4 1.219(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
C2 C1 C6 120.01(19) . . ?
C2 C1 S1 127.19(17) . . ?
C6 C1 S1 112.74(14) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 118.9(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 120.94(19) . . ?
C5 C6 N1 124.16(18) . . ?
C1 C6 N1 114.68(17) . . ?
N1 C7 C32 103.62(14) . . ?
N1 C7 S1 107.68(13) . . ?
C32 C7 S1 115.54(14) . . ?
N1 C7 H7 109.9 . . ?
C32 C7 H7 109.9 . . ?
S1 C7 H7 109.9 . . ?
N1 C8 C9 111.45(16) . . ?
N1 C8 C17 105.59(14) . . ?
C9 C8 C17 112.46(15) . . ?
N1 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
C17 C8 H8 109.1 . . ?
O1 C9 C10 121.20(18) . . ?
O1 C9 C8 120.28(17) . . ?
C10 C9 C8 118.43(17) . . ?
C11 C10 C16 118.75(19) . . ?
C11 C10 C9 123.30(18) . . ?
C16 C10 C9 117.95(18) . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 121.6(2) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C15 118.0(2) . . ?
C12 C13 C14 122.3(2) . . ?
C15 C13 C14 119.7(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 121.6(2) . . ?
C16 C15 H15 119.2 . . ?
C13 C15 H15 119.2 . . ?
C15 C16 C10 120.1(2) . . ?
C15 C16 H16 119.9 . . ?
C10 C16 H16 119.9 . . ?
C18 C17 C32 113.35(16) . . ?
C18 C17 C8 114.85(15) . . ?
C32 C17 C8 102.89(15) . . ?
C18 C17 H17 108.5 . . ?
C32 C17 H17 108.5 . . ?
C8 C17 H17 108.5 . . ?
C23 C18 C19 118.04(17) . . ?
C23 C18 C17 121.18(17) . . ?
C19 C18 C17 120.77(17) . . ?
C20 C19 C18 120.30(19) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 121.14(19) . . ?
C19 C20 Br1 119.96(16) . . ?
C21 C20 Br1 118.90(15) . . ?
C22 C21 C20 119.21(19) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C23 119.97(19) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
O2 C23 C18 122.32(17) . . ?
O2 C23 C22 116.34(18) . . ?
C18 C23 C22 121.31(18) . . ?
C25 C24 C30 120.5(2) . . ?
C25 C24 H24 119.7 . . ?
C30 C24 H24 119.7 . . ?
C24 C25 C26 121.5(2) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C25 C26 C28 117.6(2) . . ?
C25 C26 C27 120.7(2) . . ?
C28 C26 C27 121.6(2) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 C29 121.3(2) . . ?
C26 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C30 C29 C28 120.5(2) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C24 118.48(19) . . ?
C29 C30 C31 119.97(17) . . ?
C24 C30 C31 121.51(18) . . ?
O2 C31 C30 106.37(15) . . ?
O2 C31 C32 110.43(15) . . ?
C30 C31 C32 117.02(16) . . ?
O2 C31 H31 107.5 . . ?
C30 C31 H31 107.5 . . ?
C32 C31 H31 107.5 . . ?
N2 C32 C7 111.60(15) . . ?
N2 C32 C17 111.78(16) . . ?
C7 C32 C17 104.23(15) . . ?
N2 C32 C31 107.49(15) . . ?
C7 C32 C31 111.84(16) . . ?
C17 C32 C31 109.95(15) . . ?
C6 N1 C7 109.26(14) . . ?
C6 N1 C8 111.94(15) . . ?
C7 N1 C8 110.38(14) . . ?
O3 N2 O4 124.24(17) . . ?
O3 N2 C32 117.60(16) . . ?
O4 N2 C32 118.05(17) . . ?
C23 O2 C31 116.78(14) . . ?
C1 S1 C7 88.69(9) . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_5h
_database_code_depnum_ccdc_archive 'CCDC 1546838'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H22 Br N O4 S'
_chemical_formula_sum            'C32 H22 Br N O4 S'
_chemical_formula_weight         596.47

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   12.3329(12)
_cell_length_b                   13.8610(12)
_cell_length_c                   16.0666(15)
_cell_angle_alpha                90
_cell_angle_beta                 106.912(3)
_cell_angle_gamma                90
_cell_volume                     2627.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7995
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      23.87

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.684
_shelx_estimated_absorpt_T_min   0.669
_shelx_estimated_absorpt_T_max   0.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_T_max  0.690
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32870
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5164
_reflns_number_gt                3083
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0846P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5164
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.74189(4) 0.82901(3) 0.17518(3) 0.0687(2) Uani 1 1 d . . . . .
C1 C 1.0043(3) 0.4548(3) 0.7000(2) 0.0467(9) Uani 1 1 d . . . . .
C2 C 1.0696(3) 0.4296(3) 0.7823(3) 0.0604(11) Uani 1 1 d . . . . .
H2 H 1.0651 0.3678 0.8036 0.072 Uiso 1 1 calc R U . . .
C3 C 1.1413(4) 0.4968(4) 0.8323(3) 0.0691(12) Uani 1 1 d . . . . .
H3 H 1.1875 0.4798 0.8872 0.083 Uiso 1 1 calc R U . . .
C4 C 1.1453(3) 0.5901(4) 0.8014(3) 0.0675(12) Uani 1 1 d . . . . .
H4 H 1.1921 0.6357 0.8368 0.081 Uiso 1 1 calc R U . . .
C5 C 1.0806(3) 0.6158(3) 0.7187(2) 0.0535(10) Uani 1 1 d . . . . .
H5 H 1.0843 0.6780 0.6981 0.064 Uiso 1 1 calc R U . . .
C6 C 1.0105(3) 0.5479(3) 0.6669(2) 0.0434(9) Uani 1 1 d . . . . .
C7 C 0.8729(3) 0.4744(2) 0.5527(2) 0.0390(8) Uani 1 1 d . . . . .
C8 C 0.9035(2) 0.6284(2) 0.5173(2) 0.0375(8) Uani 1 1 d . . . . .
C9 C 0.9619(3) 0.7215(2) 0.5264(2) 0.0398(8) Uani 1 1 d . . . . .
C10 C 0.8977(3) 0.8074(2) 0.4871(2) 0.0395(8) Uani 1 1 d . . . . .
C11 C 0.9494(3) 0.8768(3) 0.4494(2) 0.0484(9) Uani 1 1 d . . . . .
H11 H 1.0261 0.8706 0.4543 0.058 Uiso 1 1 calc R U . . .
C12 C 0.8913(3) 0.9537(3) 0.4054(3) 0.0510(10) Uani 1 1 d . . . . .
H12 H 0.9274 0.9979 0.3789 0.061 Uiso 1 1 calc R U . . .
C13 C 0.7776(3) 0.9654(3) 0.4003(2) 0.0464(9) Uani 1 1 d . . . . .
C14 C 0.7546(4) 1.0937(3) 0.2977(3) 0.0781(13) Uani 1 1 d . . . . .
H14A H 0.8203 1.1290 0.3302 0.117 Uiso 1 1 calc R U . . .
H14B H 0.6976 1.1381 0.2663 0.117 Uiso 1 1 calc R U . . .
H14C H 0.7749 1.0513 0.2575 0.117 Uiso 1 1 calc R U . . .
C15 C 0.7262(3) 0.9012(3) 0.4425(2) 0.0462(9) Uani 1 1 d . . . . .
H15 H 0.6520 0.9120 0.4430 0.055 Uiso 1 1 calc R U . . .
C16 C 0.7835(3) 0.8216(2) 0.4838(2) 0.0414(8) Uani 1 1 d . . . . .
H16 H 0.7468 0.7771 0.5095 0.050 Uiso 1 1 calc R U . . .
C17 C 0.6532(3) 0.5663(2) 0.3226(2) 0.0434(9) Uani 1 1 d . . . . .
C18 C 0.5835(3) 0.5907(3) 0.2409(3) 0.0554(10) Uani 1 1 d . . . . .
H18 H 0.5191 0.5541 0.2158 0.066 Uiso 1 1 calc R U . . .
C19 C 0.6085(3) 0.6687(3) 0.1966(3) 0.0541(10) Uani 1 1 d . . . . .
H19 H 0.5612 0.6858 0.1421 0.065 Uiso 1 1 calc R U . . .
C20 C 0.7056(3) 0.7210(3) 0.2353(2) 0.0429(8) Uani 1 1 d . . . . .
C21 C 0.7765(3) 0.6970(3) 0.3155(2) 0.0399(8) Uani 1 1 d . . . . .
H21 H 0.8426 0.7323 0.3389 0.048 Uiso 1 1 calc R U . . .
C22 C 0.7504(3) 0.6203(2) 0.3625(2) 0.0384(8) Uani 1 1 d . . . . .
C23 C 0.8170(2) 0.5878(2) 0.4501(2) 0.0374(8) Uani 1 1 d . . . . .
C24 C 0.7983(3) 0.4920(2) 0.4728(2) 0.0385(8) Uani 1 1 d . . . . .
C25 C 0.7110(3) 0.4289(2) 0.4147(2) 0.0444(9) Uani 1 1 d . . . . .
H25 H 0.7450 0.3940 0.3754 0.053 Uiso 1 1 calc R U . . .
C26 C 0.6615(3) 0.3572(3) 0.4640(2) 0.0434(9) Uani 1 1 d . . . . .
C27 C 0.6043(3) 0.3865(3) 0.5220(3) 0.0568(11) Uani 1 1 d . . . . .
H27 H 0.5919 0.4520 0.5278 0.068 Uiso 1 1 calc R U . . .
C28 C 0.5651(3) 0.3215(3) 0.5713(3) 0.0575(11) Uani 1 1 d . . . . .
H28 H 0.5252 0.3429 0.6089 0.069 Uiso 1 1 calc R U . . .
C29 C 0.5855(3) 0.2240(3) 0.5645(3) 0.0490(9) Uani 1 1 d . . . . .
C30 C 0.5246(4) 0.1839(3) 0.6893(3) 0.0782(14) Uani 1 1 d . . . . .
H30A H 0.5844 0.2228 0.7253 0.117 Uiso 1 1 calc R U . . .
H30B H 0.5137 0.1280 0.7213 0.117 Uiso 1 1 calc R U . . .
H30C H 0.4558 0.2208 0.6722 0.117 Uiso 1 1 calc R U . . .
C31 C 0.6400(3) 0.1938(3) 0.5061(3) 0.0496(9) Uani 1 1 d . . . . .
H31 H 0.6511 0.1281 0.4997 0.059 Uiso 1 1 calc R U . . .
C32 C 0.6782(3) 0.2586(3) 0.4573(3) 0.0479(9) Uani 1 1 d . . . . .
H32 H 0.7161 0.2364 0.4187 0.057 Uiso 1 1 calc R U . . .
N1 N 0.9384(2) 0.5556(2) 0.58078(18) 0.0386(7) Uani 1 1 d . . . . .
O1 O 0.7114(2) 1.03826(19) 0.35625(19) 0.0629(8) Uani 1 1 d . . . . .
O2 O 1.06428(19) 0.72719(19) 0.56396(17) 0.0560(7) Uani 1 1 d . . . . .
O3 O 0.61966(18) 0.48902(18) 0.36361(17) 0.0528(7) Uani 1 1 d . . . . .
O4 O 0.5544(2) 0.15393(18) 0.6132(2) 0.0645(8) Uani 1 1 d . . . . .
S1 S 0.90572(8) 0.38081(7) 0.62718(7) 0.0527(3) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C20 1.904(3) . ?
C1 C2 1.378(5) . ?
C1 C6 1.406(5) . ?
C1 S1 1.753(4) . ?
C2 C3 1.372(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(5) . ?
C5 H5 0.9300 . ?
C6 N1 1.415(4) . ?
C7 C24 1.366(5) . ?
C7 N1 1.383(4) . ?
C7 S1 1.731(3) . ?
C8 C23 1.396(4) . ?
C8 N1 1.409(4) . ?
C8 C9 1.465(5) . ?
C9 O2 1.234(4) . ?
C9 C10 1.467(5) . ?
C10 C11 1.387(5) . ?
C10 C16 1.408(5) . ?
C11 C12 1.362(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(5) . ?
C12 H12 0.9300 . ?
C13 O1 1.360(4) . ?
C13 C15 1.380(5) . ?
C14 O1 1.432(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.372(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O3 1.383(4) . ?
C17 C18 1.386(5) . ?
C17 C22 1.400(5) . ?
C18 C19 1.378(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(5) . ?
C21 C22 1.395(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.479(5) . ?
C23 C24 1.413(5) . ?
C24 C25 1.488(5) . ?
C25 O3 1.449(4) . ?
C25 C26 1.507(5) . ?
C25 H25 0.9800 . ?
C26 C27 1.383(5) . ?
C26 C32 1.391(5) . ?
C27 C28 1.377(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.384(5) . ?
C28 H28 0.9300 . ?
C29 C31 1.369(5) . ?
C29 O4 1.371(4) . ?
C30 O4 1.436(5) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.364(5) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.0(4) . . ?
C2 C1 S1 126.2(3) . . ?
C6 C1 S1 112.9(3) . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 119.2(4) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 N1 130.0(3) . . ?
C1 C6 N1 110.6(3) . . ?
C24 C7 N1 109.3(3) . . ?
C24 C7 S1 137.9(3) . . ?
N1 C7 S1 112.8(3) . . ?
C23 C8 N1 106.0(3) . . ?
C23 C8 C9 132.4(3) . . ?
N1 C8 C9 121.4(3) . . ?
O2 C9 C8 120.6(3) . . ?
O2 C9 C10 120.4(3) . . ?
C8 C9 C10 119.0(3) . . ?
C11 C10 C16 117.9(3) . . ?
C11 C10 C9 119.4(3) . . ?
C16 C10 C9 122.6(3) . . ?
C12 C11 C10 122.0(3) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 119.5(3) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
O1 C13 C15 116.2(3) . . ?
O1 C13 C12 124.1(3) . . ?
C15 C13 C12 119.7(3) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 120.7(3) . . ?
C16 C15 H15 119.6 . . ?
C13 C15 H15 119.6 . . ?
C15 C16 C10 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C10 C16 H16 120.0 . . ?
O3 C17 C18 116.8(3) . . ?
O3 C17 C22 122.1(3) . . ?
C18 C17 C22 121.0(3) . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 118.2(4) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
C21 C20 C19 121.8(3) . . ?
C21 C20 Br1 119.2(3) . . ?
C19 C20 Br1 119.0(3) . . ?
C20 C21 C22 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C17 117.5(3) . . ?
C21 C22 C23 126.5(3) . . ?
C17 C22 C23 115.9(3) . . ?
C8 C23 C24 108.9(3) . . ?
C8 C23 C22 134.5(3) . . ?
C24 C23 C22 116.4(3) . . ?
C7 C24 C23 107.1(3) . . ?
C7 C24 C25 130.6(3) . . ?
C23 C24 C25 122.3(3) . . ?
O3 C25 C24 108.5(3) . . ?
O3 C25 C26 108.1(2) . . ?
C24 C25 C26 112.8(3) . . ?
O3 C25 H25 109.1 . . ?
C24 C25 H25 109.1 . . ?
C26 C25 H25 109.1 . . ?
C27 C26 C32 117.2(3) . . ?
C27 C26 C25 121.7(3) . . ?
C32 C26 C25 121.0(3) . . ?
C28 C27 C26 121.9(3) . . ?
C28 C27 H27 119.0 . . ?
C26 C27 H27 119.0 . . ?
C27 C28 C29 119.3(3) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C31 C29 O4 116.7(3) . . ?
C31 C29 C28 119.4(3) . . ?
O4 C29 C28 124.0(3) . . ?
O4 C30 H30A 109.5 . . ?
O4 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O4 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C29 120.8(3) . . ?
C32 C31 H31 119.6 . . ?
C29 C31 H31 119.6 . . ?
C31 C32 C26 121.2(3) . . ?
C31 C32 H32 119.4 . . ?
C26 C32 H32 119.4 . . ?
C7 N1 C8 108.7(3) . . ?
C7 N1 C6 113.5(3) . . ?
C8 N1 C6 137.3(3) . . ?
C13 O1 C14 117.2(3) . . ?
C17 O3 C25 115.1(2) . . ?
C29 O4 C30 117.7(3) . . ?
C7 S1 C1 90.01(18) . . ?

_refine_diff_density_max         0.516
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.094

####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1546830'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

#=================================================================== data_3a 

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H23 Br N2 O4 S'
_chemical_formula_sum            'C31 H23 Br N2 O4 S'
_chemical_formula_weight         599.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.303(2)
_cell_length_b                   12.821(2)
_cell_length_c                   20.763(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.403(7)
_cell_angle_gamma                90
_cell_volume                     2695.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4496
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      26.12

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    1.643
_shelx_estimated_absorpt_T_min   0.621
_shelx_estimated_absorpt_T_max   0.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.597
_exptl_absorpt_correction_T_max  0.674
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14481
_diffrn_reflns_av_unetI/netI     0.0937
_diffrn_reflns_av_R_equivalents  0.1354
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.929
_diffrn_reflns_theta_max         24.710
_diffrn_reflns_theta_full        24.710
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4589
_reflns_number_gt                3233
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0854P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4589
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1534
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.76940(5) 0.34928(4) 1.13125(3) 0.0725(2) Uani 1 1 d . . . . .
C1 C 0.6520(4) 0.3121(3) 0.9120(2) 0.0511(10) Uani 1 1 d . . . . .
H1 H 0.7405 0.3171 0.9217 0.061 Uiso 1 1 calc R U . . .
C2 C 0.6047(6) 0.2235(3) 0.9313(2) 0.0699(14) Uani 1 1 d . . . . .
H2 H 0.6633 0.1709 0.9571 0.084 Uiso 1 1 calc R U . . .
C3 C 0.4757(6) 0.2126(4) 0.9133(3) 0.0695(14) Uani 1 1 d . . . . .
H3 H 0.4451 0.1513 0.9246 0.083 Uiso 1 1 calc R U . . .
C4 C 0.3881(5) 0.2916(3) 0.8782(2) 0.0626(12) Uani 1 1 d . . . . .
H4 H 0.2990 0.2833 0.8662 0.075 Uiso 1 1 calc R U . . .
C5 C 0.4308(4) 0.3818(3) 0.8609(2) 0.0451(9) Uani 1 1 d . . . . .
H5 H 0.3713 0.4354 0.8380 0.054 Uiso 1 1 calc R U . . .
C6 C 0.5641(4) 0.3938(3) 0.87741(17) 0.0373(8) Uani 1 1 d . . . . .
C7 C 0.6182(3) 0.4895(3) 0.86023(16) 0.0328(8) Uani 1 1 d . . . . .
C8 C 0.5573(3) 0.5941(2) 0.86527(16) 0.0300(7) Uani 1 1 d . . . . .
H8 H 0.4696 0.5820 0.8626 0.036 Uiso 1 1 calc R U . . .
C9 C 0.5933(3) 0.7679(2) 0.83239(17) 0.0323(8) Uani 1 1 d . . . . .
H9 H 0.6333 0.7999 0.8039 0.039 Uiso 1 1 calc R U . . .
C10 C 0.4105(3) 0.6737(3) 0.75179(16) 0.0340(8) Uani 1 1 d . . . . .
C11 C 0.3443(4) 0.5964(3) 0.70256(19) 0.0468(10) Uani 1 1 d . . . . .
H11 H 0.3879 0.5373 0.6983 0.056 Uiso 1 1 calc R U . . .
C12 C 0.2073(4) 0.6109(3) 0.6588(2) 0.0569(12) Uani 1 1 d . . . . .
H12 H 0.1591 0.5590 0.6265 0.068 Uiso 1 1 calc R U . . .
C13 C 0.1447(4) 0.6997(3) 0.6633(2) 0.0483(10) Uani 1 1 d . . . . .
H13 H 0.0553 0.7084 0.6328 0.058 Uiso 1 1 calc R U . . .
C14 C 0.2118(3) 0.7764(3) 0.71232(19) 0.0424(9) Uani 1 1 d . . . . .
H14 H 0.1680 0.8364 0.7151 0.051 Uiso 1 1 calc R U . . .
C15 C 0.3449(3) 0.7637(3) 0.75742(17) 0.0365(8) Uani 1 1 d . . . . .
C16 C 0.8823(3) 0.6102(3) 1.01477(16) 0.0335(8) Uani 1 1 d . . . . .
C17 C 0.9802(4) 0.5544(3) 1.07039(17) 0.0413(9) Uani 1 1 d . . . . .
H17 H 1.0687 0.5694 1.0841 0.050 Uiso 1 1 calc R U . . .
C18 C 0.9469(4) 0.4781(3) 1.10469(18) 0.0425(9) Uani 1 1 d . . . . .
H18 H 1.0125 0.4396 1.1410 0.051 Uiso 1 1 calc R U . . .
C19 C 0.8136(4) 0.4576(3) 1.08538(18) 0.0424(9) Uani 1 1 d . . . . .
C20 C 0.7155(3) 0.5146(3) 1.03162(17) 0.0347(8) Uani 1 1 d . . . . .
H20 H 0.6271 0.5021 1.0197 0.042 Uiso 1 1 calc R U . . .
C21 C 0.7506(3) 0.5920(3) 0.99491(15) 0.0306(7) Uani 1 1 d . . . . .
C22 C 0.6444(3) 0.6551(2) 0.93606(16) 0.0310(8) Uani 1 1 d . . . . .
H22 H 0.5859 0.6838 0.9551 0.037 Uiso 1 1 calc R U . . .
C23 C 0.7000(3) 0.7468(3) 0.90971(16) 0.0309(8) Uani 1 1 d . . . . .
C24 C 0.8325(3) 0.7158(3) 0.91141(17) 0.0345(8) Uani 1 1 d . . . . .
H24 H 0.8163 0.6540 0.8809 0.041 Uiso 1 1 calc R U . . .
C25 C 0.9046(3) 0.7949(3) 0.88669(17) 0.0339(8) Uani 1 1 d . . . . .
C26 C 0.8773(4) 0.8000(3) 0.81557(19) 0.0439(9) Uani 1 1 d . . . . .
H26 H 0.8139 0.7561 0.7824 0.053 Uiso 1 1 calc R U . . .
C27 C 0.9443(4) 0.8705(3) 0.7930(2) 0.0491(10) Uani 1 1 d . . . . .
H27 H 0.9245 0.8735 0.7445 0.059 Uiso 1 1 calc R U . . .
C28 C 1.0407(4) 0.9371(3) 0.8412(2) 0.0481(10) Uani 1 1 d . . . . .
C29 C 1.1120(5) 1.0129(4) 0.8174(3) 0.0660(13) Uani 1 1 d . . . . .
H29A H 1.1795 1.0467 0.8587 0.099 Uiso 1 1 calc R U . . .
H29B H 1.0510 1.0642 0.7868 0.099 Uiso 1 1 calc R U . . .
H29C H 1.1518 0.9771 0.7914 0.099 Uiso 1 1 calc R U . . .
C30 C 1.0646(4) 0.9299(3) 0.91274(19) 0.0436(9) Uani 1 1 d . . . . .
H30 H 1.1270 0.9738 0.9464 0.052 Uiso 1 1 calc R U . . .
C31 C 0.9994(3) 0.8603(3) 0.93519(18) 0.0384(9) Uani 1 1 d . . . . .
H31 H 1.0190 0.8570 0.9836 0.046 Uiso 1 1 calc R U . . .
N1 N 0.5448(3) 0.6645(2) 0.80511(13) 0.0311(6) Uani 1 1 d . . . . .
N2 N 0.7235(3) 0.8413(2) 0.95675(15) 0.0378(7) Uani 1 1 d . . . . .
O1 O 0.7102(2) 0.48711(19) 0.84661(13) 0.0431(6) Uani 1 1 d . . . . .
O2 O 0.7139(3) 0.9266(2) 0.92863(14) 0.0567(8) Uani 1 1 d . . . . .
O3 O 0.7564(3) 0.8277(2) 1.02021(14) 0.0643(9) Uani 1 1 d . . . . .
O4 O 0.9240(2) 0.68578(19) 0.98339(12) 0.0404(6) Uani 1 1 d . . . . .
S1 S 0.44994(9) 0.84795(7) 0.82577(5) 0.0430(3) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C19 1.873(4) . ?
C1 C2 1.389(6) . ?
C1 C6 1.403(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.342(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.361(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.483(5) . ?
C7 O1 1.194(4) . ?
C7 C8 1.532(4) . ?
C8 N1 1.495(4) . ?
C8 C22 1.567(4) . ?
C8 H8 0.9800 . ?
C9 N1 1.450(4) . ?
C9 C23 1.544(4) . ?
C9 S1 1.871(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.380(5) . ?
C10 C15 1.404(5) . ?
C10 N1 1.432(4) . ?
C11 C12 1.417(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(5) . ?
C14 H14 0.9300 . ?
C15 S1 1.759(3) . ?
C16 O4 1.363(4) . ?
C16 C21 1.377(5) . ?
C16 C17 1.390(5) . ?
C17 C18 1.358(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.401(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(5) . ?
C20 C21 1.411(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.512(4) . ?
C22 C23 1.543(5) . ?
C22 H22 0.9800 . ?
C23 N2 1.504(4) . ?
C23 C24 1.534(5) . ?
C24 O4 1.441(4) . ?
C24 C25 1.525(5) . ?
C24 H24 0.9800 . ?
C25 C26 1.369(5) . ?
C25 C31 1.381(5) . ?
C26 C27 1.388(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.395(5) . ?
C27 H27 0.9300 . ?
C28 C30 1.390(5) . ?
C28 C29 1.481(5) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.364(5) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
N2 O3 1.212(4) . ?
N2 O2 1.222(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
C2 C1 C6 118.8(4) . . ?
C2 C1 H1 120.6 . . ?
C6 C1 H1 120.6 . . ?
C3 C2 C1 121.0(4) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.0(4) . . ?
C5 C6 C7 123.2(3) . . ?
C1 C6 C7 117.8(3) . . ?
O1 C7 C6 122.1(3) . . ?
O1 C7 C8 120.3(3) . . ?
C6 C7 C8 117.5(3) . . ?
N1 C8 C7 110.4(3) . . ?
N1 C8 C22 105.6(2) . . ?
C7 C8 C22 112.8(2) . . ?
N1 C8 H8 109.3 . . ?
C7 C8 H8 109.3 . . ?
C22 C8 H8 109.3 . . ?
N1 C9 C23 103.4(2) . . ?
N1 C9 S1 108.0(2) . . ?
C23 C9 S1 115.0(2) . . ?
N1 C9 H9 110.1 . . ?
C23 C9 H9 110.1 . . ?
S1 C9 H9 110.1 . . ?
C11 C10 C15 121.3(3) . . ?
C11 C10 N1 123.5(3) . . ?
C15 C10 N1 114.9(3) . . ?
C10 C11 C12 117.3(4) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
C13 C12 C11 121.2(4) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 121.0(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 119.5(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C10 119.7(3) . . ?
C14 C15 S1 127.9(3) . . ?
C10 C15 S1 112.3(2) . . ?
O4 C16 C21 122.3(3) . . ?
O4 C16 C17 116.5(3) . . ?
C21 C16 C17 121.1(3) . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.9(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 Br1 120.2(3) . . ?
C18 C19 Br1 119.3(3) . . ?
C19 C20 C21 119.4(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C16 C21 C20 118.9(3) . . ?
C16 C21 C22 121.0(3) . . ?
C20 C21 C22 120.0(3) . . ?
C21 C22 C23 113.1(3) . . ?
C21 C22 C8 115.6(3) . . ?
C23 C22 C8 103.5(2) . . ?
C21 C22 H22 108.1 . . ?
C23 C22 H22 108.1 . . ?
C8 C22 H22 108.1 . . ?
N2 C23 C24 107.8(3) . . ?
N2 C23 C22 111.4(3) . . ?
C24 C23 C22 110.0(3) . . ?
N2 C23 C9 111.4(3) . . ?
C24 C23 C9 111.9(3) . . ?
C22 C23 C9 104.4(3) . . ?
O4 C24 C25 106.4(3) . . ?
O4 C24 C23 109.6(3) . . ?
C25 C24 C23 118.9(3) . . ?
O4 C24 H24 107.1 . . ?
C25 C24 H24 107.1 . . ?
C23 C24 H24 107.1 . . ?
C26 C25 C31 119.1(3) . . ?
C26 C25 C24 119.8(3) . . ?
C31 C25 C24 121.1(3) . . ?
C25 C26 C27 120.0(3) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C28 121.7(3) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 H27 119.1 . . ?
C30 C28 C27 116.4(4) . . ?
C30 C28 C29 121.6(4) . . ?
C27 C28 C29 122.0(4) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C28 122.1(3) . . ?
C31 C30 H30 119.0 . . ?
C28 C30 H30 119.0 . . ?
C30 C31 C25 120.7(3) . . ?
C30 C31 H31 119.7 . . ?
C25 C31 H31 119.7 . . ?
C10 N1 C9 108.2(2) . . ?
C10 N1 C8 111.7(3) . . ?
C9 N1 C8 110.3(2) . . ?
O3 N2 O2 124.6(3) . . ?
O3 N2 C23 118.1(3) . . ?
O2 N2 C23 117.3(3) . . ?
C16 O4 C24 116.4(2) . . ?
C15 S1 C9 88.51(15) . . ?

_refine_diff_density_max         0.405
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_3n
_database_code_depnum_ccdc_archive 'CCDC 1546832'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H23 Br N2 O5 S'
_chemical_formula_sum            'C31 H23 Br N2 O5 S'
_chemical_formula_weight         615.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   16.7535(18)
_cell_length_b                   7.6164(8)
_cell_length_c                   24.6930(19)
_cell_angle_alpha                90
_cell_angle_beta                 120.576(5)
_cell_angle_gamma                90
_cell_volume                     2712.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9901
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      26.73

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    1.637
_shelx_estimated_absorpt_T_min   0.657
_shelx_estimated_absorpt_T_max   0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_T_max  0.675
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26050
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.478
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6183
_reflns_number_gt                4066
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+0.6214P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6183
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.32879(2) 0.55342(4) 0.80699(2) 0.07885(14) Uani 1 1 d . . . . .
C1 C 0.52901(16) 0.9183(3) 0.78212(11) 0.0475(5) Uani 1 1 d . . . . .
H1 H 0.5824 0.8724 0.7849 0.057 Uiso 1 1 calc R U . . .
C2 C 0.44624(16) 0.9077(3) 0.72636(11) 0.0503(5) Uani 1 1 d . . . . .
H2 H 0.4439 0.8557 0.6915 0.060 Uiso 1 1 calc R U . . .
C3 C 0.36585(16) 0.9747(3) 0.72180(11) 0.0508(5) Uani 1 1 d . . . . .
C4 C 0.20174(18) 1.0057(5) 0.65914(15) 0.0838(9) Uani 1 1 d . . . . .
H4A H 0.2027 1.1290 0.6676 0.126 Uiso 1 1 calc R U . . .
H4B H 0.1931 0.9401 0.6890 0.126 Uiso 1 1 calc R U . . .
H4C H 0.1517 0.9812 0.6174 0.126 Uiso 1 1 calc R U . . .
C5 C 0.36975(16) 1.0529(3) 0.77349(11) 0.0549(6) Uani 1 1 d . . . . .
H5 H 0.3161 1.0969 0.7709 0.066 Uiso 1 1 calc R U . . .
C6 C 0.45314(15) 1.0654(3) 0.82874(11) 0.0508(5) Uani 1 1 d . . . . .
H6 H 0.4555 1.1211 0.8631 0.061 Uiso 1 1 calc R U . . .
C7 C 0.53402(14) 0.9970(3) 0.83463(10) 0.0420(5) Uani 1 1 d . . . . .
C8 C 0.62120(14) 1.0114(3) 0.89642(10) 0.0431(5) Uani 1 1 d . . . . .
C9 C 0.69504(13) 0.8679(3) 0.91493(10) 0.0418(5) Uani 1 1 d . . . . .
H9 H 0.6895 0.8175 0.8766 0.050 Uiso 1 1 calc R U . . .
C10 C 0.83884(13) 0.8499(3) 1.01478(10) 0.0465(5) Uani 1 1 d . . . . .
H10 H 0.8702 0.9375 1.0482 0.056 Uiso 1 1 calc R U . . .
C11 C 0.91951(14) 0.8301(3) 0.95157(11) 0.0531(6) Uani 1 1 d . . . . .
C12 C 0.97555(16) 0.8175(4) 0.92503(14) 0.0663(7) Uani 1 1 d . . . . .
H12 H 1.0262 0.7421 0.9419 0.080 Uiso 1 1 calc R U . . .
C13 C 0.95417(19) 0.9191(4) 0.87346(14) 0.0750(9) Uani 1 1 d . . . . .
H13 H 0.9912 0.9118 0.8555 0.090 Uiso 1 1 calc R U . . .
C14 C 0.8798(2) 1.0308(4) 0.84775(14) 0.0766(8) Uani 1 1 d . . . . .
H14 H 0.8669 1.0979 0.8127 0.092 Uiso 1 1 calc R U . . .
C15 C 0.82352(18) 1.0443(4) 0.87390(13) 0.0664(7) Uani 1 1 d . . . . .
H15 H 0.7729 1.1200 0.8567 0.080 Uiso 1 1 calc R U . . .
C16 C 0.84403(15) 0.9442(3) 0.92550(11) 0.0500(6) Uani 1 1 d . . . . .
C17 C 0.82814(16) 1.1051(3) 1.13143(12) 0.0568(6) Uani 1 1 d . . . . .
H17 H 0.8113 1.1794 1.0974 0.068 Uiso 1 1 calc R U . . .
C18 C 0.88799(19) 1.1643(5) 1.19071(15) 0.0774(8) Uani 1 1 d . . . . .
H18 H 0.9112 1.2780 1.1967 0.093 Uiso 1 1 calc R U . . .
C19 C 0.9139(2) 1.0579(6) 1.24117(16) 0.0925(11) Uani 1 1 d . . . . .
H19 H 0.9557 1.0976 1.2815 0.111 Uiso 1 1 calc R U . . .
C20 C 0.8781(2) 0.8924(6) 1.23221(14) 0.0887(10) Uani 1 1 d . . . . .
H20 H 0.8954 0.8202 1.2668 0.106 Uiso 1 1 calc R U . . .
C21 C 0.81588(19) 0.8297(4) 1.17193(12) 0.0708(7) Uani 1 1 d . . . . .
H21 H 0.7910 0.7174 1.1663 0.085 Uiso 1 1 calc R U . . .
C22 C 0.79188(15) 0.9374(3) 1.12075(11) 0.0512(6) Uani 1 1 d . . . . .
C23 C 0.72541(14) 0.8797(3) 1.05441(10) 0.0485(5) Uani 1 1 d . . . . .
H23 H 0.7020 0.9864 1.0288 0.058 Uiso 1 1 calc R U . . .
C24 C 0.76340(14) 0.7593(3) 1.02191(10) 0.0455(5) Uani 1 1 d . . . . .
C25 C 0.68630(13) 0.7172(3) 0.95469(10) 0.0428(5) Uani 1 1 d . . . . .
H25 H 0.7013 0.6058 0.9421 0.051 Uiso 1 1 calc R U . . .
C26 C 0.59152(14) 0.7001(3) 0.94783(10) 0.0447(5) Uani 1 1 d . . . . .
C27 C 0.51718(15) 0.6388(3) 0.89212(11) 0.0497(5) Uani 1 1 d . . . . .
H27 H 0.5259 0.6034 0.8595 0.060 Uiso 1 1 calc R U . . .
C28 C 0.43029(15) 0.6301(3) 0.88513(12) 0.0534(6) Uani 1 1 d . . . . .
C29 C 0.41578(16) 0.6795(3) 0.93302(13) 0.0608(6) Uani 1 1 d . . . . .
H29 H 0.3566 0.6745 0.9275 0.073 Uiso 1 1 calc R U . . .
C30 C 0.48942(16) 0.7365(3) 0.98900(12) 0.0614(6) Uani 1 1 d . . . . .
H30 H 0.4805 0.7682 1.0219 0.074 Uiso 1 1 calc R U . . .
C31 C 0.57698(15) 0.7466(3) 0.99640(11) 0.0507(5) Uani 1 1 d . . . . .
N1 N 0.78941(11) 0.9380(2) 0.95455(8) 0.0447(4) Uani 1 1 d . . . . .
N2 N 0.80022(15) 0.5932(3) 1.06012(11) 0.0614(5) Uani 1 1 d . . . . .
O1 O 0.28729(12) 0.9567(2) 0.66425(8) 0.0714(5) Uani 1 1 d . . . . .
O2 O 0.63268(11) 1.1298(2) 0.93265(8) 0.0601(4) Uani 1 1 d . . . . .
O3 O 0.74760(15) 0.4695(3) 1.04556(12) 0.0910(7) Uani 1 1 d . . . . .
O4 O 0.87994(13) 0.5944(3) 1.10451(9) 0.0826(6) Uani 1 1 d . . . . .
O5 O 0.64823(10) 0.7985(2) 1.05429(7) 0.0601(4) Uani 1 1 d . . . . .
S1 S 0.92700(4) 0.70374(9) 1.01334(3) 0.06313(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C28 1.902(2) . ?
C1 C2 1.372(3) . ?
C1 C7 1.392(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.390(3) . ?
C2 H2 0.9300 . ?
C3 O1 1.367(3) . ?
C3 C5 1.379(3) . ?
C4 O1 1.423(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.372(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.485(3) . ?
C8 O2 1.214(3) . ?
C8 C9 1.536(3) . ?
C9 N1 1.473(3) . ?
C9 C25 1.565(3) . ?
C9 H9 0.9800 . ?
C10 N1 1.447(3) . ?
C10 C24 1.527(3) . ?
C10 S1 1.864(2) . ?
C10 H10 0.9800 . ?
C11 C16 1.393(3) . ?
C11 C12 1.395(3) . ?
C11 S1 1.753(3) . ?
C12 C13 1.373(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(3) . ?
C15 H15 0.9300 . ?
C16 N1 1.422(3) . ?
C17 C18 1.363(4) . ?
C17 C22 1.381(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.359(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.364(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.397(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.504(3) . ?
C23 O5 1.432(3) . ?
C23 C24 1.553(3) . ?
C23 H23 0.9800 . ?
C24 N2 1.509(3) . ?
C24 C25 1.531(3) . ?
C25 C26 1.514(3) . ?
C25 H25 0.9800 . ?
C26 C27 1.385(3) . ?
C26 C31 1.386(3) . ?
C27 C28 1.378(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.375(4) . ?
C29 C30 1.373(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.385(3) . ?
C30 H30 0.9300 . ?
C31 O5 1.374(3) . ?
N2 O3 1.213(3) . ?
N2 O4 1.223(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
C2 C1 C7 120.8(2) . . ?
C2 C1 H1 119.6 . . ?
C7 C1 H1 119.6 . . ?
C1 C2 C3 120.2(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O1 C3 C5 124.9(2) . . ?
O1 C3 C2 115.4(2) . . ?
C5 C3 C2 119.7(2) . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 119.7(2) . . ?
C6 C5 H5 120.2 . . ?
C3 C5 H5 120.2 . . ?
C5 C6 C7 121.6(2) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C1 118.1(2) . . ?
C6 C7 C8 118.50(19) . . ?
C1 C7 C8 123.42(19) . . ?
O2 C8 C7 121.08(19) . . ?
O2 C8 C9 120.48(19) . . ?
C7 C8 C9 118.37(18) . . ?
N1 C9 C8 111.68(17) . . ?
N1 C9 C25 105.11(16) . . ?
C8 C9 C25 112.97(16) . . ?
N1 C9 H9 109.0 . . ?
C8 C9 H9 109.0 . . ?
C25 C9 H9 109.0 . . ?
N1 C10 C24 104.69(16) . . ?
N1 C10 S1 107.58(14) . . ?
C24 C10 S1 116.25(16) . . ?
N1 C10 H10 109.4 . . ?
C24 C10 H10 109.4 . . ?
S1 C10 H10 109.4 . . ?
C16 C11 C12 119.7(2) . . ?
C16 C11 S1 113.01(16) . . ?
C12 C11 S1 127.1(2) . . ?
C13 C12 C11 118.5(3) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C14 C13 C12 121.8(2) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 118.8(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C11 121.1(2) . . ?
C15 C16 N1 124.5(2) . . ?
C11 C16 N1 114.3(2) . . ?
C18 C17 C22 121.5(3) . . ?
C18 C17 H17 119.2 . . ?
C22 C17 H17 119.2 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 119.5(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C21 121.1(3) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 C20 118.9(3) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C17 C22 C21 118.6(2) . . ?
C17 C22 C23 119.2(2) . . ?
C21 C22 C23 122.1(2) . . ?
O5 C23 C22 107.23(17) . . ?
O5 C23 C24 110.54(18) . . ?
C22 C23 C24 117.69(18) . . ?
O5 C23 H23 107.0 . . ?
C22 C23 H23 107.0 . . ?
C24 C23 H23 107.0 . . ?
N2 C24 C10 110.61(17) . . ?
N2 C24 C25 110.71(19) . . ?
C10 C24 C25 105.12(17) . . ?
N2 C24 C23 108.46(17) . . ?
C10 C24 C23 111.92(18) . . ?
C25 C24 C23 110.01(16) . . ?
C26 C25 C24 113.44(18) . . ?
C26 C25 C9 114.85(17) . . ?
C24 C25 C9 103.31(16) . . ?
C26 C25 H25 108.3 . . ?
C24 C25 H25 108.3 . . ?
C9 C25 H25 108.3 . . ?
C27 C26 C31 118.72(19) . . ?
C27 C26 C25 120.14(19) . . ?
C31 C26 C25 121.14(19) . . ?
C28 C27 C26 120.0(2) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C29 C28 C27 121.1(2) . . ?
C29 C28 Br1 119.90(17) . . ?
C27 C28 Br1 118.96(19) . . ?
C30 C29 C28 119.4(2) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C29 C30 C31 120.0(2) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
O5 C31 C30 117.0(2) . . ?
O5 C31 C26 122.11(18) . . ?
C30 C31 C26 120.8(2) . . ?
C16 N1 C10 110.80(17) . . ?
C16 N1 C9 115.21(17) . . ?
C10 N1 C9 111.98(16) . . ?
O3 N2 O4 124.7(2) . . ?
O3 N2 C24 117.5(2) . . ?
O4 N2 C24 117.8(2) . . ?
C3 O1 C4 117.3(2) . . ?
C31 O5 C23 115.61(16) . . ?
C11 S1 C10 88.97(10) . . ?

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_5g
_database_code_depnum_ccdc_archive 'CCDC 1546837'
_audit_update_record             
;
2017-05-03 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H22 Br N O3 S'
_chemical_formula_sum            'C32 H22 Br N O3 S'
_chemical_formula_weight         580.47

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   12.9498(8)
_cell_length_b                   13.3015(9)
_cell_length_c                   15.8317(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.084(2)
_cell_angle_gamma                90
_cell_volume                     2620.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6008
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      23.95

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.684
_shelx_estimated_absorpt_T_min   0.688
_shelx_estimated_absorpt_T_max   0.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_T_max  0.690
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23835
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.241
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5130
_reflns_number_gt                3264
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1184P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5130
_refine_ls_number_parameters     345
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1091
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.1920
_refine_ls_wR_factor_gt          0.1739
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.74775(4) 0.84448(4) 1.21636(3) 0.0596(2) Uani 1 1 d . . . . .
C1 C 1.0103(3) 0.4716(4) 0.7988(3) 0.0467(11) Uani 1 1 d . . . . .
C2 C 1.0725(4) 0.4491(4) 0.7432(3) 0.0595(14) Uani 1 1 d . . . . .
H2 H 1.0692 0.3859 0.7174 0.071 Uiso 1 1 calc R U . . .
C3 C 1.1402(5) 0.5231(5) 0.7264(4) 0.0713(16) Uani 1 1 d . . . . .
H3 H 1.1836 0.5093 0.6899 0.086 Uiso 1 1 calc R U . . .
C4 C 1.1430(4) 0.6174(5) 0.7643(4) 0.0682(16) Uani 1 1 d . . . . .
H4 H 1.1872 0.6668 0.7514 0.082 Uiso 1 1 calc R U . . .
C5 C 1.0818(4) 0.6399(4) 0.8206(3) 0.0533(13) Uani 1 1 d . . . . .
H5 H 1.0846 0.7033 0.8458 0.064 Uiso 1 1 calc R U . . .
C6 C 1.0156(3) 0.5651(3) 0.8388(3) 0.0401(10) Uani 1 1 d . . . . .
C7 C 0.8869(3) 0.4828(3) 0.8913(3) 0.0353(10) Uani 1 1 d . . . . .
C8 C 0.9126(3) 0.6411(3) 0.9452(3) 0.0345(10) Uani 1 1 d . . . . .
C9 C 0.9588(4) 0.7424(3) 0.9610(3) 0.0430(11) Uani 1 1 d . . . . .
C10 C 0.8875(4) 0.8250(3) 0.9678(3) 0.0432(11) Uani 1 1 d . . . . .
C11 C 0.7794(4) 0.8271(3) 0.9214(3) 0.0494(12) Uani 1 1 d . . . . .
H11 H 0.7511 0.7765 0.8811 0.059 Uiso 1 1 calc R U . . .
C12 C 0.7142(5) 0.9029(4) 0.9347(3) 0.0600(14) Uani 1 1 d . . . . .
H12 H 0.6423 0.9045 0.9024 0.072 Uiso 1 1 calc R U . . .
C13 C 0.7551(5) 0.9772(4) 0.9962(4) 0.0636(15) Uani 1 1 d . . . . .
C14 C 0.7314(6) 1.1201(5) 1.0844(5) 0.1024(15) Uani 1 1 d . U . . .
H14A H 0.7557 1.0829 1.1382 0.154 Uiso 1 1 calc R U . . .
H14B H 0.6770 1.1671 1.0892 0.154 Uiso 1 1 calc R U . . .
H14C H 0.7908 1.1558 1.0734 0.154 Uiso 1 1 calc R U . . .
C15 C 0.8626(5) 0.9784(4) 1.0409(4) 0.0698(17) Uani 1 1 d . . . . .
H15 H 0.8906 1.0295 1.0807 0.084 Uiso 1 1 calc R U . . .
C16 C 0.9274(4) 0.9037(4) 1.0259(3) 0.0600(14) Uani 1 1 d . . . . .
H16 H 1.0004 0.9053 1.0552 0.072 Uiso 1 1 calc R U . . .
C17 C 0.6770(3) 0.5675(3) 1.0304(3) 0.0377(10) Uani 1 1 d . . . . .
C18 C 0.6053(4) 0.5941(4) 1.0777(3) 0.0495(12) Uani 1 1 d . . . . .
H18 H 0.5434 0.5562 1.0723 0.059 Uiso 1 1 calc R U . . .
C19 C 0.6259(4) 0.6771(4) 1.1329(3) 0.0493(12) Uani 1 1 d . . . . .
H19 H 0.5778 0.6958 1.1641 0.059 Uiso 1 1 calc R U . . .
C20 C 0.7184(3) 0.7309(3) 1.1408(3) 0.0378(10) Uani 1 1 d . . . . .
C21 C 0.7905(3) 0.7047(3) 1.0945(3) 0.0384(10) Uani 1 1 d . . . . .
H21 H 0.8543 0.7404 1.1032 0.046 Uiso 1 1 calc R U . . .
C22 C 0.7683(3) 0.6253(3) 1.0347(3) 0.0329(9) Uani 1 1 d . . . . .
C23 C 0.8327(3) 0.5945(3) 0.9750(3) 0.0333(9) Uani 1 1 d . . . . .
C24 C 0.8166(3) 0.4967(3) 0.9401(3) 0.0351(9) Uani 1 1 d . . . . .
C25 C 0.7332(3) 0.4272(3) 0.9568(3) 0.0397(10) Uani 1 1 d . . . . .
H25 H 0.7655 0.3852 1.0082 0.048 Uiso 1 1 calc R U . . .
C26 C 0.6815(3) 0.3621(3) 0.8802(3) 0.0393(10) Uani 1 1 d . . . . .
C27 C 0.6818(4) 0.2586(4) 0.8880(4) 0.0575(13) Uani 1 1 d . . . . .
H27 H 0.7145 0.2286 0.9419 0.069 Uiso 1 1 calc R U . . .
C28 C 0.6334(5) 0.1993(4) 0.8156(5) 0.0741(18) Uani 1 1 d . . . . .
H28 H 0.6360 0.1298 0.8221 0.089 Uiso 1 1 calc R U . . .
C29 C 0.5832(4) 0.2380(5) 0.7369(5) 0.0712(17) Uani 1 1 d . . . . .
C30 C 0.5312(7) 0.1735(6) 0.6585(6) 0.133(4) Uani 1 1 d . . . . .
H30A H 0.5690 0.1108 0.6628 0.199 Uiso 1 1 calc R U . . .
H30B H 0.5338 0.2076 0.6056 0.199 Uiso 1 1 calc R U . . .
H30C H 0.4577 0.1610 0.6569 0.199 Uiso 1 1 calc R U . . .
C31 C 0.5813(4) 0.3435(4) 0.7291(4) 0.0652(16) Uani 1 1 d . . . . .
H31 H 0.5467 0.3731 0.6756 0.078 Uiso 1 1 calc R U . . .
C32 C 0.6305(4) 0.4038(4) 0.8002(3) 0.0554(13) Uani 1 1 d . . . . .
H32 H 0.6289 0.4733 0.7937 0.066 Uiso 1 1 calc R U . . .
N1 N 0.9469(2) 0.5689(3) 0.8947(2) 0.0359(8) Uani 1 1 d . . . . .
O1 O 0.6859(4) 1.0497(3) 1.0107(3) 0.0923(12) Uani 1 1 d . U . . .
O2 O 1.0556(3) 0.7557(3) 0.9716(2) 0.0654(10) Uani 1 1 d . . . . .
O3 O 0.6478(2) 0.4881(2) 0.9738(2) 0.0480(8) Uani 1 1 d . . . . .
S1 S 0.91835(10) 0.39044(10) 0.82561(8) 0.0513(4) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C20 1.898(4) . ?
C1 C2 1.381(6) . ?
C1 C6 1.389(6) . ?
C1 S1 1.745(5) . ?
C2 C3 1.391(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(6) . ?
C5 H5 0.9300 . ?
C6 N1 1.420(5) . ?
C7 C24 1.360(5) . ?
C7 N1 1.377(5) . ?
C7 S1 1.730(4) . ?
C8 C23 1.395(5) . ?
C8 N1 1.398(5) . ?
C8 C9 1.468(6) . ?
C9 O2 1.230(5) . ?
C9 C10 1.458(6) . ?
C10 C11 1.389(7) . ?
C10 C16 1.395(6) . ?
C11 C12 1.367(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(7) . ?
C12 H12 0.9300 . ?
C13 C15 1.376(8) . ?
C13 O1 1.379(6) . ?
C14 O1 1.484(8) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.363(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O3 1.369(5) . ?
C17 C18 1.390(6) . ?
C17 C22 1.395(5) . ?
C18 C19 1.387(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(6) . ?
C21 C22 1.394(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.482(5) . ?
C23 C24 1.406(6) . ?
C24 C25 1.499(5) . ?
C25 O3 1.455(5) . ?
C25 C26 1.491(6) . ?
C25 H25 0.9800 . ?
C26 C32 1.372(7) . ?
C26 C27 1.382(6) . ?
C27 C28 1.391(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.339(9) . ?
C28 H28 0.9300 . ?
C29 C31 1.409(8) . ?
C29 C30 1.506(8) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.385(7) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.4(5) . . ?
C2 C1 S1 125.4(4) . . ?
C6 C1 S1 113.2(3) . . ?
C1 C2 C3 118.6(5) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 120.0(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 121.6(5) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 118.4(5) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 120.0(4) . . ?
C1 C6 N1 110.8(4) . . ?
C5 C6 N1 129.1(4) . . ?
C24 C7 N1 108.9(4) . . ?
C24 C7 S1 138.1(3) . . ?
N1 C7 S1 113.0(3) . . ?
C23 C8 N1 105.7(3) . . ?
C23 C8 C9 131.0(4) . . ?
N1 C8 C9 123.3(3) . . ?
O2 C9 C10 121.6(4) . . ?
O2 C9 C8 120.5(4) . . ?
C10 C9 C8 117.9(4) . . ?
C11 C10 C16 117.9(5) . . ?
C11 C10 C9 122.9(4) . . ?
C16 C10 C9 119.1(5) . . ?
C12 C11 C10 120.5(5) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.1(5) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C15 C13 O1 121.2(5) . . ?
C15 C13 C12 120.3(5) . . ?
O1 C13 C12 118.5(6) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 119.1(5) . . ?
C16 C15 H15 120.5 . . ?
C13 C15 H15 120.5 . . ?
C15 C16 C10 121.9(5) . . ?
C15 C16 H16 119.1 . . ?
C10 C16 H16 119.1 . . ?
O3 C17 C18 116.3(3) . . ?
O3 C17 C22 122.3(3) . . ?
C18 C17 C22 121.1(4) . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 118.9(4) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 121.4(4) . . ?
C19 C20 Br1 119.4(3) . . ?
C21 C20 Br1 119.2(3) . . ?
C20 C21 C22 120.6(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C17 117.6(4) . . ?
C21 C22 C23 126.6(4) . . ?
C17 C22 C23 115.8(3) . . ?
C8 C23 C24 108.8(3) . . ?
C8 C23 C22 133.9(4) . . ?
C24 C23 C22 117.2(3) . . ?
C7 C24 C23 107.3(4) . . ?
C7 C24 C25 130.2(4) . . ?
C23 C24 C25 122.5(3) . . ?
O3 C25 C26 106.3(3) . . ?
O3 C25 C24 108.1(3) . . ?
C26 C25 C24 113.4(3) . . ?
O3 C25 H25 109.6 . . ?
C26 C25 H25 109.6 . . ?
C24 C25 H25 109.6 . . ?
C32 C26 C27 118.3(5) . . ?
C32 C26 C25 120.6(4) . . ?
C27 C26 C25 121.1(4) . . ?
C26 C27 C28 120.1(5) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C29 C28 C27 122.8(6) . . ?
C29 C28 H28 118.6 . . ?
C27 C28 H28 118.6 . . ?
C28 C29 C31 117.1(5) . . ?
C28 C29 C30 122.6(7) . . ?
C31 C29 C30 120.2(7) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C29 120.9(6) . . ?
C32 C31 H31 119.6 . . ?
C29 C31 H31 119.6 . . ?
C26 C32 C31 120.7(5) . . ?
C26 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C7 N1 C8 109.2(3) . . ?
C7 N1 C6 113.0(3) . . ?
C8 N1 C6 137.2(4) . . ?
C13 O1 C14 116.0(5) . . ?
C17 O3 C25 117.7(3) . . ?
C7 S1 C1 89.8(2) . . ?

_refine_diff_density_max         1.605
_refine_diff_density_min         -1.213
_refine_diff_density_rms         0.092

