# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cd17395
_database_code_depnum_ccdc_archive 'CCDC 1561913'
_audit_update_record             
;
2017-07-13 deposited with the CCDC.
2017-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 Br2 N2 O3 S'
_chemical_formula_weight         592.34

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      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                   8.4549(14)
_cell_length_b                   13.872(2)
_cell_length_c                   14.009(2)
_cell_angle_alpha                117.552(3)
_cell_angle_beta                 101.368(4)
_cell_angle_gamma                92.964(4)
_cell_volume                     1408.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1590
_cell_measurement_theta_min      4.982
_cell_measurement_theta_max      41.086

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.977
_shelx_estimated_absorpt_T_min   0.560
_shelx_estimated_absorpt_T_max   0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4434
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            8150
_diffrn_reflns_av_unetI/netI     0.0823
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.679
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5227
_reflns_number_gt                3182
_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 SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0614P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5227
_refine_ls_number_parameters     304
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_restrained_S_all      0.919
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.269 0.240 0.291 122 49 ' '
2 -0.269 0.760 0.709 122 49 ' '
_platon_squeeze_details          
;
;


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 0.76151(6) 0.35291(4) 0.18771(5) 0.0773(2) Uani 1 1 d . . . . .
Br2 Br 0.93748(6) 0.81821(4) 0.42608(5) 0.0881(2) Uani 1 1 d . . . . .
S1 S 0.29541(15) 0.92215(9) 0.29400(10) 0.0702(4) Uani 1 1 d . . . . .
N1 N 0.5475(4) 0.7952(3) 0.3821(3) 0.0584(10) Uani 1 1 d D . . . .
N2 N 0.2860(4) 0.7978(3) 0.2729(3) 0.0580(9) Uani 1 1 d . . . . .
O1 O 0.3357(4) 0.9892(2) 0.4119(3) 0.0838(10) Uani 1 1 d . . . . .
O2 O 0.1485(4) 0.9274(2) 0.2273(3) 0.0885(11) Uani 1 1 d . . . . .
O3 O 0.2419(3) 0.5983(2) 0.3475(2) 0.0562(7) Uani 1 1 d . . . . .
C1 C 0.6133(4) 0.7010(3) 0.3458(3) 0.0479(10) Uani 1 1 d . . . . .
C2 C 0.7781(5) 0.6894(3) 0.3544(3) 0.0575(11) Uani 1 1 d . . . . .
C3 C 0.8223(5) 0.5864(3) 0.3092(3) 0.0543(10) Uani 1 1 d . . . . .
H3 H 0.9318 0.5785 0.3156 0.065 Uiso 1 1 calc R U . . .
C4 C 0.7013(5) 0.4955(3) 0.2544(3) 0.0492(10) Uani 1 1 d . . . . .
C5 C 0.5381(4) 0.5029(3) 0.2436(3) 0.0433(9) Uani 1 1 d . . . . .
H5 H 0.4585 0.4401 0.2066 0.052 Uiso 1 1 calc R U . . .
C6 C 0.4961(4) 0.6070(3) 0.2894(3) 0.0416(9) Uani 1 1 d . . . . .
C7 C 0.3283(4) 0.6405(3) 0.2943(3) 0.0457(9) Uani 1 1 d . . . . .
C8 C 0.3722(5) 0.7691(3) 0.3555(3) 0.0525(10) Uani 1 1 d . . . . .
H8 H 0.3319 0.8018 0.4230 0.063 Uiso 1 1 calc R U . . .
C9 C 0.2611(5) 0.7044(3) 0.1622(3) 0.0563(11) Uani 1 1 d . . . . .
H9A H 0.3604 0.6979 0.1365 0.068 Uiso 1 1 calc R U . . .
H9B H 0.1741 0.7099 0.1091 0.068 Uiso 1 1 calc R U . . .
C10 C 0.2145(4) 0.6102(3) 0.1811(3) 0.0464(9) Uani 1 1 d . . . . .
H10 H 0.1036 0.6147 0.1921 0.056 Uiso 1 1 calc R U . . .
C11 C 0.2088(5) 0.4952(3) 0.0888(3) 0.0476(10) Uani 1 1 d . . . . .
C12 C 0.1297(5) 0.4063(4) 0.0898(4) 0.0631(12) Uani 1 1 d . . . . .
H12 H 0.0777 0.4182 0.1461 0.076 Uiso 1 1 calc R U . . .
C13 C 0.1266(7) 0.3006(4) 0.0092(5) 0.0800(15) Uani 1 1 d . . . . .
H13 H 0.0745 0.2417 0.0121 0.096 Uiso 1 1 calc R U . . .
C14 C 0.1990(7) 0.2812(4) -0.0749(4) 0.0803(16) Uani 1 1 d . . . . .
H14 H 0.1953 0.2095 -0.1303 0.096 Uiso 1 1 calc R U . . .
C15 C 0.2756(7) 0.3666(4) -0.0770(4) 0.0771(15) Uani 1 1 d . . . . .
H15 H 0.3260 0.3533 -0.1343 0.092 Uiso 1 1 calc R U . . .
C16 C 0.2821(6) 0.4747(3) 0.0040(3) 0.0630(12) Uani 1 1 d . . . . .
H16 H 0.3359 0.5328 0.0005 0.076 Uiso 1 1 calc R U . . .
C17 C 0.3291(6) 0.6157(5) 0.4538(4) 0.0843(16) Uani 1 1 d . . . . .
H17A H 0.3792 0.6925 0.5003 0.101 Uiso 1 1 calc R U . . .
H17B H 0.4153 0.5710 0.4453 0.101 Uiso 1 1 calc R U . . .
C18 C 0.2161(9) 0.5857(7) 0.5067(5) 0.128(3) Uani 1 1 d . . . . .
H18A H 0.1453 0.6397 0.5292 0.192 Uiso 1 1 calc R U . . .
H18B H 0.2775 0.5833 0.5707 0.192 Uiso 1 1 calc R U . . .
H18C H 0.1518 0.5147 0.4548 0.192 Uiso 1 1 calc R U . . .
C19 C 0.4553(6) 0.9483(3) 0.2418(4) 0.0684(13) Uani 1 1 d . . . . .
C20 C 0.4267(7) 0.9146(4) 0.1295(5) 0.0826(15) Uani 1 1 d . . . . .
H20 H 0.3242 0.8772 0.0826 0.099 Uiso 1 1 calc R U . . .
C21 C 0.5465(8) 0.9356(4) 0.0875(5) 0.0896(17) Uani 1 1 d . . . . .
H21 H 0.5261 0.9107 0.0115 0.108 Uiso 1 1 calc R U . . .
C22 C 0.6996(7) 0.9935(4) 0.1554(6) 0.0872(16) Uani 1 1 d . . . . .
C23 C 0.7291(7) 1.0245(4) 0.2674(5) 0.0887(16) Uani 1 1 d . . . . .
H23 H 0.8323 1.0604 0.3140 0.106 Uiso 1 1 calc R U . . .
C24 C 0.6072(7) 1.0028(4) 0.3104(5) 0.0848(16) Uani 1 1 d . . . . .
H24 H 0.6278 1.0251 0.3860 0.102 Uiso 1 1 calc R U . . .
C25 C 0.8319(8) 1.0206(6) 0.1098(6) 0.120(2) Uani 1 1 d . . . . .
H25A H 0.9213 0.9830 0.1184 0.180 Uiso 1 1 calc R U . . .
H25B H 0.8697 1.0987 0.1495 0.180 Uiso 1 1 calc R U . . .
H25C H 0.7892 0.9974 0.0323 0.180 Uiso 1 1 calc R U . . .
H1 H 0.597(4) 0.848(2) 0.439(2) 0.042(11) Uiso 1 1 d 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 C4 1.904(4) . ?
Br2 C2 1.891(4) . ?
S1 O1 1.426(3) . ?
S1 O2 1.427(3) . ?
S1 N2 1.605(4) . ?
S1 C19 1.754(6) . ?
N1 C1 1.359(5) . ?
N1 C8 1.439(5) . ?
N1 H1 0.803(18) . ?
N2 C9 1.453(5) . ?
N2 C8 1.467(5) . ?
O3 C7 1.416(5) . ?
O3 C17 1.427(5) . ?
C1 C6 1.382(5) . ?
C1 C2 1.399(5) . ?
C2 C3 1.376(5) . ?
C3 C4 1.374(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(5) . ?
C5 C6 1.381(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.520(5) . ?
C7 C10 1.536(5) . ?
C7 C8 1.564(5) . ?
C8 H8 0.9800 . ?
C9 C10 1.497(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.510(5) . ?
C10 H10 0.9800 . ?
C11 C16 1.369(6) . ?
C11 C12 1.379(6) . ?
C12 C13 1.371(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.358(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.335(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.469(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C24 1.373(7) . ?
C19 C20 1.382(7) . ?
C20 C21 1.350(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.388(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(8) . ?
C22 C25 1.504(8) . ?
C23 C24 1.377(8) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.3(2) . . ?
O1 S1 N2 105.1(2) . . ?
O2 S1 N2 107.38(18) . . ?
O1 S1 C19 109.5(2) . . ?
O2 S1 C19 106.2(2) . . ?
N2 S1 C19 107.8(2) . . ?
C1 N1 C8 110.0(3) . . ?
C1 N1 H1 119(3) . . ?
C8 N1 H1 121(3) . . ?
C9 N2 C8 109.5(3) . . ?
C9 N2 S1 121.9(3) . . ?
C8 N2 S1 122.9(2) . . ?
C7 O3 C17 116.1(3) . . ?
N1 C1 C6 112.8(3) . . ?
N1 C1 C2 128.5(4) . . ?
C6 C1 C2 118.6(3) . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 Br2 121.0(3) . . ?
C1 C2 Br2 118.5(3) . . ?
C4 C3 C2 118.7(4) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 122.8(3) . . ?
C5 C4 Br1 118.4(3) . . ?
C3 C4 Br1 118.8(3) . . ?
C4 C5 C6 117.7(3) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C5 C6 C1 121.7(3) . . ?
C5 C6 C7 129.4(3) . . ?
C1 C6 C7 108.8(3) . . ?
O3 C7 C6 113.7(3) . . ?
O3 C7 C10 107.4(3) . . ?
C6 C7 C10 114.8(3) . . ?
O3 C7 C8 114.2(3) . . ?
C6 C7 C8 101.6(3) . . ?
C10 C7 C8 104.8(3) . . ?
N1 C8 N2 114.2(4) . . ?
N1 C8 C7 106.6(3) . . ?
N2 C8 C7 102.9(3) . . ?
N1 C8 H8 110.9 . . ?
N2 C8 H8 110.9 . . ?
C7 C8 H8 110.9 . . ?
N2 C9 C10 101.6(3) . . ?
N2 C9 H9A 111.5 . . ?
C10 C9 H9A 111.5 . . ?
N2 C9 H9B 111.5 . . ?
C10 C9 H9B 111.5 . . ?
H9A C9 H9B 109.3 . . ?
C9 C10 C11 117.5(3) . . ?
C9 C10 C7 103.7(3) . . ?
C11 C10 C7 115.6(3) . . ?
C9 C10 H10 106.4 . . ?
C11 C10 H10 106.4 . . ?
C7 C10 H10 106.4 . . ?
C16 C11 C12 118.0(4) . . ?
C16 C11 C10 122.4(4) . . ?
C12 C11 C10 119.5(4) . . ?
C13 C12 C11 121.0(5) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.6(5) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 119.0(4) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 121.9(5) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C11 C16 C15 119.6(5) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
O3 C17 C18 109.6(4) . . ?
O3 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
O3 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 119.5(6) . . ?
C24 C19 S1 121.4(4) . . ?
C20 C19 S1 119.1(4) . . ?
C21 C20 C19 120.4(5) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 121.4(6) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C23 C22 C21 118.0(6) . . ?
C23 C22 C25 120.3(6) . . ?
C21 C22 C25 121.7(6) . . ?
C24 C23 C22 120.7(5) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C19 C24 C23 120.0(5) . . ?
C19 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N2 C9 -174.7(3) . . . . ?
O2 S1 N2 C9 56.1(4) . . . . ?
C19 S1 N2 C9 -58.0(4) . . . . ?
O1 S1 N2 C8 -24.0(4) . . . . ?
O2 S1 N2 C8 -153.2(3) . . . . ?
C19 S1 N2 C8 92.7(4) . . . . ?
C8 N1 C1 C6 2.8(5) . . . . ?
C8 N1 C1 C2 179.8(4) . . . . ?
N1 C1 C2 C3 -177.9(4) . . . . ?
C6 C1 C2 C3 -1.1(6) . . . . ?
N1 C1 C2 Br2 0.5(6) . . . . ?
C6 C1 C2 Br2 177.4(3) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
Br2 C2 C3 C4 -177.6(3) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C2 C3 C4 Br1 178.1(3) . . . . ?
C3 C4 C5 C6 0.6(6) . . . . ?
Br1 C4 C5 C6 -178.0(3) . . . . ?
C4 C5 C6 C1 -0.9(6) . . . . ?
C4 C5 C6 C7 -177.5(4) . . . . ?
N1 C1 C6 C5 178.4(4) . . . . ?
C2 C1 C6 C5 1.1(6) . . . . ?
N1 C1 C6 C7 -4.3(5) . . . . ?
C2 C1 C6 C7 178.3(3) . . . . ?
C17 O3 C7 C6 50.4(5) . . . . ?
C17 O3 C7 C10 178.5(4) . . . . ?
C17 O3 C7 C8 -65.7(5) . . . . ?
C5 C6 C7 O3 57.6(5) . . . . ?
C1 C6 C7 O3 -119.4(3) . . . . ?
C5 C6 C7 C10 -66.7(5) . . . . ?
C1 C6 C7 C10 116.4(4) . . . . ?
C5 C6 C7 C8 -179.2(4) . . . . ?
C1 C6 C7 C8 3.9(4) . . . . ?
C1 N1 C8 N2 -113.0(4) . . . . ?
C1 N1 C8 C7 -0.1(5) . . . . ?
C9 N2 C8 N1 90.6(4) . . . . ?
S1 N2 C8 N1 -63.2(4) . . . . ?
C9 N2 C8 C7 -24.5(4) . . . . ?
S1 N2 C8 C7 -178.3(3) . . . . ?
O3 C7 C8 N1 120.6(3) . . . . ?
C6 C7 C8 N1 -2.2(4) . . . . ?
C10 C7 C8 N1 -122.1(3) . . . . ?
O3 C7 C8 N2 -118.8(3) . . . . ?
C6 C7 C8 N2 118.3(3) . . . . ?
C10 C7 C8 N2 -1.6(4) . . . . ?
C8 N2 C9 C10 41.2(4) . . . . ?
S1 N2 C9 C10 -164.7(3) . . . . ?
N2 C9 C10 C11 -168.8(3) . . . . ?
N2 C9 C10 C7 -39.8(4) . . . . ?
O3 C7 C10 C9 147.4(3) . . . . ?
C6 C7 C10 C9 -85.0(4) . . . . ?
C8 C7 C10 C9 25.5(4) . . . . ?
O3 C7 C10 C11 -82.5(4) . . . . ?
C6 C7 C10 C11 45.1(5) . . . . ?
C8 C7 C10 C11 155.7(3) . . . . ?
C9 C10 C11 C16 16.8(6) . . . . ?
C7 C10 C11 C16 -106.3(5) . . . . ?
C9 C10 C11 C12 -164.3(4) . . . . ?
C7 C10 C11 C12 72.6(5) . . . . ?
C16 C11 C12 C13 0.9(6) . . . . ?
C10 C11 C12 C13 -178.0(4) . . . . ?
C11 C12 C13 C14 -1.3(7) . . . . ?
C12 C13 C14 C15 1.0(8) . . . . ?
C13 C14 C15 C16 -0.5(8) . . . . ?
C12 C11 C16 C15 -0.4(6) . . . . ?
C10 C11 C16 C15 178.5(4) . . . . ?
C14 C15 C16 C11 0.2(7) . . . . ?
C7 O3 C17 C18 169.9(5) . . . . ?
O1 S1 C19 C24 15.4(5) . . . . ?
O2 S1 C19 C24 146.7(4) . . . . ?
N2 S1 C19 C24 -98.4(4) . . . . ?
O1 S1 C19 C20 -163.6(3) . . . . ?
O2 S1 C19 C20 -32.3(4) . . . . ?
N2 S1 C19 C20 82.6(4) . . . . ?
C24 C19 C20 C21 -0.4(7) . . . . ?
S1 C19 C20 C21 178.7(4) . . . . ?
C19 C20 C21 C22 -1.6(8) . . . . ?
C20 C21 C22 C23 3.3(8) . . . . ?
C20 C21 C22 C25 -177.9(5) . . . . ?
C21 C22 C23 C24 -3.0(8) . . . . ?
C25 C22 C23 C24 178.1(5) . . . . ?
C20 C19 C24 C23 0.6(8) . . . . ?
S1 C19 C24 C23 -178.4(4) . . . . ?
C22 C23 C24 C19 1.1(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.803(18) 2.19(2) 2.972(4) 164(3) 2_676
C3 H3 O3 0.93 2.55 3.466(5) 168.5 1_655
C3 H3 O3 0.93 2.55 3.466(5) 168.5 1_655
N1 H1 O1 0.803(18) 2.19(2) 2.972(4) 164(3) 2_676

_refine_diff_density_max         0.550
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-4

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

data_mo_d8v17274_0m
_database_code_depnum_ccdc_archive 'CCDC 1570336'
_audit_update_record             
;
2017-08-23 deposited with the CCDC.
2017-09-08 downloaded from the CCDC.
;
_audit_creation_date             2017-08-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C44 H45 Br2 N3 O6 S2'
_chemical_formula_sum            'C44 H45 Br2 N3 O6 S2'
_chemical_formula_weight         935.77
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.823(2)
_cell_length_b                   11.5473(19)
_cell_length_c                   30.267(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.559(6)
_cell_angle_gamma                90
_cell_volume                     4777.3(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4075
_cell_measurement_temperature    272(2)
_cell_measurement_theta_max      21.610
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.771
_shelx_estimated_absorpt_T_min   0.689
_exptl_absorpt_coefficient_mu    1.830
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0882 before and 0.0552 after correction. The Ratio of minimum to maximum transmission is 0.7598. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.1150
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            22460
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         2.698
_diffrn_ambient_temperature      272.29
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4890
_reflns_number_total             10781
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     518
_refine_ls_number_reflns         10781
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1540
_refine_ls_R_factor_gt           0.0663
_refine_ls_restrained_S_all      0.941
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1030P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.2048
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C15(H15A,H15B), C36(H36A,H36B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C13(H13), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C31(H31), C32(H32), C33(H33),
  C34(H34), C35(H35), C39(H39), C40(H40), C42(H42), C43(H43)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C29(H29A,H29B,H29C), C37(H37A,H37B,H37C), C44(H44A,H44B,
 H44C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.52219(4) 0.19632(5) 0.32009(2) 0.0598(2) Uani 1 1 d . . . . .
Br2 Br 0.23176(5) 0.86905(6) 0.46524(3) 0.0854(3) Uani 1 1 d . . . . .
S1 S 0.40245(10) 0.22661(13) 0.43879(5) 0.0529(4) Uani 1 1 d . . . . .
S2 S 0.11894(9) 0.20139(12) 0.30382(5) 0.0479(3) Uani 1 1 d . . . . .
O1 O 0.5681(2) 0.4471(3) 0.41495(11) 0.0460(9) Uani 1 1 d . . . . .
O2 O 0.0275(2) 0.4563(3) 0.38687(11) 0.0479(9) Uani 1 1 d . . . . .
O3 O 0.2986(3) 0.2241(4) 0.43391(13) 0.0628(11) Uani 1 1 d . . . . .
O4 O 0.4595(3) 0.2556(4) 0.48089(12) 0.0678(11) Uani 1 1 d . . . . .
O5 O 0.2081(3) 0.1422(3) 0.32061(14) 0.0618(11) Uani 1 1 d . . . . .
O6 O 0.0805(3) 0.1947(3) 0.25742(11) 0.0561(10) Uani 1 1 d . . . . .
N1 N 0.4291(3) 0.3236(4) 0.40230(13) 0.0393(10) Uani 1 1 d . . . . .
N2 N 0.2761(2) 0.4198(4) 0.36766(13) 0.0398(10) Uani 1 1 d . . . . .
N3 N 0.1385(3) 0.3401(4) 0.31410(13) 0.0422(10) Uani 1 1 d . . . . .
C1 C 0.3564(3) 0.3497(5) 0.36089(16) 0.0416(12) Uani 1 1 d . . . . .
H1 H 0.3320 0.2767 0.3470 0.050 Uiso 1 1 calc R . . . .
C2 C 0.4231(3) 0.4078(5) 0.33165(16) 0.0420(12) Uani 1 1 d . . . . .
H2A H 0.3998 0.3929 0.3003 0.050 Uiso 1 1 calc R . . . .
H2B H 0.4245 0.4909 0.3365 0.050 Uiso 1 1 calc R . . . .
C3 C 0.5238(3) 0.3571(4) 0.34482(16) 0.0393(11) Uani 1 1 d . . . . .
C4 C 0.5306(3) 0.3424(5) 0.39600(16) 0.0415(12) Uani 1 1 d . . . . .
H4 H 0.5722 0.2766 0.4069 0.050 Uiso 1 1 calc R . . . .
C5 C 0.1758(3) 0.3760(4) 0.36094(16) 0.0381(11) Uani 1 1 d . . . . .
H5 H 0.1675 0.3141 0.3822 0.046 Uiso 1 1 calc R . . . .
C6 C 0.0607(4) 0.4200(4) 0.29341(18) 0.0484(13) Uani 1 1 d . . . . .
H6A H -0.0037 0.3883 0.2950 0.058 Uiso 1 1 calc R . . . .
H6B H 0.0665 0.4346 0.2624 0.058 Uiso 1 1 calc R . . . .
C7 C 0.0778(3) 0.5305(5) 0.32099(16) 0.0434(12) Uani 1 1 d . . . . .
H7 H 0.0147 0.5692 0.3210 0.052 Uiso 1 1 calc R . . . .
C8 C 0.1132(3) 0.4836(4) 0.36868(15) 0.0374(11) Uani 1 1 d . . . . .
C9 C 0.1856(3) 0.5617(5) 0.39627(16) 0.0418(12) Uani 1 1 d . . . . .
C10 C 0.1689(4) 0.6624(5) 0.41742(18) 0.0502(13) Uani 1 1 d . . . . .
H10 H 0.1057 0.6877 0.4192 0.060 Uiso 1 1 calc R . . . .
C11 C 0.2516(4) 0.7267(5) 0.43654(17) 0.0498(13) Uani 1 1 d . . . . .
C12 C 0.3444(4) 0.6878(5) 0.43435(18) 0.0515(14) Uani 1 1 d . . . . .
H12 H 0.3978 0.7311 0.4474 0.062 Uiso 1 1 calc R . . . .
C13 C 0.3596(3) 0.5851(5) 0.41297(17) 0.0448(12) Uani 1 1 d . . . . .
H13 H 0.4228 0.5587 0.4120 0.054 Uiso 1 1 calc R . . . .
C14 C 0.2795(3) 0.5218(4) 0.39304(16) 0.0395(11) Uani 1 1 d . . . . .
C15 C 0.6169(5) 0.4386(7) 0.4604(2) 0.090(2) Uani 1 1 d . . . . .
H15A H 0.5686 0.4385 0.4806 0.108 Uiso 1 1 calc R . . . .
H15B H 0.6529 0.3663 0.4643 0.108 Uiso 1 1 calc R . . . .
C16 C 0.6832(6) 0.5340(8) 0.4711(3) 0.110(3) Uani 1 1 d . . . . .
H16A H 0.7227 0.5432 0.4478 0.165 Uiso 1 1 calc GR . . . .
H16B H 0.7245 0.5188 0.4989 0.165 Uiso 1 1 calc GR . . . .
H16C H 0.6465 0.6036 0.4737 0.165 Uiso 1 1 calc GR . . . .
C17 C 0.6081(3) 0.4195(4) 0.32862(17) 0.0402(12) Uani 1 1 d . . . . .
C18 C 0.5917(4) 0.4974(5) 0.29316(19) 0.0565(15) Uani 1 1 d . . . . .
H18 H 0.5281 0.5138 0.2799 0.068 Uiso 1 1 calc R . . . .
C19 C 0.6688(4) 0.5499(5) 0.2778(2) 0.0660(17) Uani 1 1 d . . . . .
H19 H 0.6568 0.6015 0.2540 0.079 Uiso 1 1 calc R . . . .
C20 C 0.7620(4) 0.5284(5) 0.2964(2) 0.0623(16) Uani 1 1 d . . . . .
H20 H 0.8138 0.5646 0.2856 0.075 Uiso 1 1 calc R . . . .
C21 C 0.7797(4) 0.4518(5) 0.3319(2) 0.0595(16) Uani 1 1 d . . . . .
H21 H 0.8436 0.4360 0.3450 0.071 Uiso 1 1 calc R . . . .
C22 C 0.7028(4) 0.3993(5) 0.34772(18) 0.0492(13) Uani 1 1 d . . . . .
H22 H 0.7151 0.3489 0.3719 0.059 Uiso 1 1 calc R . . . .
C23 C 0.4444(4) 0.0918(5) 0.4233(2) 0.0565(15) Uani 1 1 d . . . . .
C24 C 0.5341(4) 0.0513(6) 0.4439(2) 0.0714(19) Uani 1 1 d . . . . .
H24 H 0.5710 0.0935 0.4666 0.086 Uiso 1 1 calc R . . . .
C25 C 0.5680(5) -0.0545(7) 0.4298(3) 0.091(3) Uani 1 1 d . . . . .
H25 H 0.6273 -0.0832 0.4441 0.109 Uiso 1 1 calc R . . . .
C26 C 0.5174(6) -0.1171(6) 0.3959(3) 0.092(3) Uani 1 1 d . . . . .
C27 C 0.4269(6) -0.0756(6) 0.3759(3) 0.088(2) Uani 1 1 d . . . . .
H27 H 0.3908 -0.1180 0.3531 0.106 Uiso 1 1 calc R . . . .
C28 C 0.3892(5) 0.0282(6) 0.3895(2) 0.0694(18) Uani 1 1 d . . . . .
H28 H 0.3282 0.0545 0.3762 0.083 Uiso 1 1 calc R . . . .
C29 C 0.5595(7) -0.2302(6) 0.3800(4) 0.142(4) Uani 1 1 d . . . . .
H29A H 0.5596 -0.2884 0.4027 0.213 Uiso 1 1 calc GR . . . .
H29B H 0.6252 -0.2172 0.3745 0.213 Uiso 1 1 calc GR . . . .
H29C H 0.5199 -0.2557 0.3530 0.213 Uiso 1 1 calc GR . . . .
C30 C 0.1464(4) 0.6138(5) 0.30382(18) 0.0482(13) Uani 1 1 d . . . . .
C31 C 0.1349(5) 0.7340(5) 0.3095(2) 0.0639(16) Uani 1 1 d . . . . .
H31 H 0.0840 0.7616 0.3235 0.077 Uiso 1 1 calc R . . . .
C32 C 0.2000(6) 0.8116(7) 0.2942(3) 0.091(2) Uani 1 1 d . . . . .
H32 H 0.1928 0.8907 0.2985 0.109 Uiso 1 1 calc R . . . .
C33 C 0.2745(6) 0.7722(8) 0.2729(3) 0.089(2) Uani 1 1 d . . . . .
H33 H 0.3173 0.8242 0.2625 0.106 Uiso 1 1 calc R . . . .
C34 C 0.2850(5) 0.6573(7) 0.2671(2) 0.077(2) Uani 1 1 d . . . . .
H34 H 0.3359 0.6306 0.2529 0.093 Uiso 1 1 calc R . . . .
C35 C 0.2222(4) 0.5790(6) 0.28179(18) 0.0583(15) Uani 1 1 d . . . . .
H35 H 0.2308 0.5005 0.2768 0.070 Uiso 1 1 calc R . . . .
C36 C 0.0413(4) 0.4120(6) 0.43159(19) 0.0650(17) Uani 1 1 d . . . . .
H36A H 0.0821 0.4645 0.4513 0.078 Uiso 1 1 calc R . . . .
H36B H 0.0735 0.3372 0.4326 0.078 Uiso 1 1 calc R . . . .
C37 C -0.0561(5) 0.4004(7) 0.4463(2) 0.079(2) Uani 1 1 d . . . . .
H37A H -0.0975 0.3528 0.4254 0.118 Uiso 1 1 calc GR . . . .
H37B H -0.0851 0.4756 0.4476 0.118 Uiso 1 1 calc GR . . . .
H37C H -0.0486 0.3652 0.4753 0.118 Uiso 1 1 calc GR . . . .
C38 C 0.0287(4) 0.1563(5) 0.33465(19) 0.0493(13) Uani 1 1 d . . . . .
C39 C 0.0535(5) 0.1120(5) 0.3769(2) 0.0693(18) Uani 1 1 d . . . . .
H39 H 0.1186 0.0984 0.3885 0.083 Uiso 1 1 calc R . . . .
C40 C -0.0198(6) 0.0878(6) 0.4019(2) 0.084(2) Uani 1 1 d . . . . .
H40 H -0.0036 0.0570 0.4304 0.101 Uiso 1 1 calc R . . . .
C41 C -0.1182(6) 0.1089(6) 0.3851(3) 0.080(2) Uani 1 1 d . . . . .
C42 C -0.1414(5) 0.1499(6) 0.3430(2) 0.0687(17) Uani 1 1 d . . . . .
H42 H -0.2066 0.1622 0.3312 0.082 Uiso 1 1 calc R . . . .
C43 C -0.0693(4) 0.1738(5) 0.31737(19) 0.0548(14) Uani 1 1 d . . . . .
H43 H -0.0861 0.2018 0.2884 0.066 Uiso 1 1 calc R . . . .
C44 C -0.1975(7) 0.0831(9) 0.4142(3) 0.128(3) Uani 1 1 d . . . . .
H44A H -0.2159 0.1537 0.4275 0.191 Uiso 1 1 calc GR . . . .
H44B H -0.1725 0.0293 0.4373 0.191 Uiso 1 1 calc GR . . . .
H44C H -0.2536 0.0503 0.3960 0.191 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 2.001(5) . ?
Br2 C11 1.898(5) . ?
S1 O3 1.421(4) . ?
S1 O4 1.435(4) . ?
S1 N1 1.652(4) . ?
S1 C23 1.750(6) . ?
S2 O5 1.434(4) . ?
S2 O6 1.428(4) . ?
S2 N3 1.647(4) . ?
S2 C38 1.745(6) . ?
O1 C4 1.404(6) . ?
O1 C15 1.442(6) . ?
O2 C8 1.415(5) . ?
O2 C36 1.433(6) . ?
N1 C1 1.516(6) . ?
N1 C4 1.460(6) . ?
N2 C1 1.412(6) . ?
N2 C5 1.462(6) . ?
N2 C14 1.403(6) . ?
N3 C5 1.493(6) . ?
N3 C6 1.483(6) . ?
C1 H1 0.9800 . ?
C1 C2 1.525(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.508(6) . ?
C3 C4 1.547(7) . ?
C3 C17 1.512(7) . ?
C4 H4 0.9800 . ?
C5 H5 0.9800 . ?
C5 C8 1.551(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.523(7) . ?
C7 H7 0.9800 . ?
C7 C8 1.551(7) . ?
C7 C30 1.498(7) . ?
C8 C9 1.504(7) . ?
C9 C10 1.364(7) . ?
C9 C14 1.394(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.413(7) . ?
C11 C12 1.370(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.439(9) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.393(7) . ?
C17 C22 1.370(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.366(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.351(8) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(8) . ?
C21 H21 0.9300 . ?
C21 C22 1.371(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(8) . ?
C23 C28 1.390(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.398(10) . ?
C25 H25 0.9300 . ?
C25 C26 1.360(11) . ?
C26 C27 1.391(10) . ?
C26 C29 1.535(10) . ?
C27 H27 0.9300 . ?
C27 C28 1.393(9) . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.410(8) . ?
C30 C35 1.383(8) . ?
C31 H31 0.9300 . ?
C31 C32 1.397(9) . ?
C32 H32 0.9300 . ?
C32 C33 1.372(11) . ?
C33 H33 0.9300 . ?
C33 C34 1.349(11) . ?
C34 H34 0.9300 . ?
C34 C35 1.373(8) . ?
C35 H35 0.9300 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C37 1.485(8) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C39 1.372(8) . ?
C38 C43 1.392(7) . ?
C39 H39 0.9300 . ?
C39 C40 1.380(9) . ?
C40 H40 0.9300 . ?
C40 C41 1.401(10) . ?
C41 C42 1.352(9) . ?
C41 C44 1.534(10) . ?
C42 H42 0.9300 . ?
C42 C43 1.379(8) . ?
C43 H43 0.9300 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 120.7(3) . . ?
O3 S1 N1 105.5(2) . . ?
O3 S1 C23 108.9(3) . . ?
O4 S1 N1 106.7(2) . . ?
O4 S1 C23 106.6(3) . . ?
N1 S1 C23 107.9(2) . . ?
O5 S2 N3 106.8(2) . . ?
O5 S2 C38 108.3(3) . . ?
O6 S2 O5 119.8(2) . . ?
O6 S2 N3 105.4(2) . . ?
O6 S2 C38 108.6(2) . . ?
N3 S2 C38 107.4(2) . . ?
C4 O1 C15 115.0(4) . . ?
C8 O2 C36 116.4(4) . . ?
C1 N1 S1 120.1(3) . . ?
C4 N1 S1 120.2(3) . . ?
C4 N1 C1 113.2(4) . . ?
C1 N2 C5 122.1(4) . . ?
C14 N2 C1 126.7(4) . . ?
C14 N2 C5 108.7(3) . . ?
C5 N3 S2 118.2(3) . . ?
C6 N3 S2 115.9(3) . . ?
C6 N3 C5 110.8(4) . . ?
N1 C1 H1 109.1 . . ?
N1 C1 C2 100.6(3) . . ?
N2 C1 N1 115.7(4) . . ?
N2 C1 H1 109.1 . . ?
N2 C1 C2 112.8(4) . . ?
C2 C1 H1 109.1 . . ?
C1 C2 H2A 110.4 . . ?
C1 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C3 C2 C1 106.8(4) . . ?
C3 C2 H2A 110.4 . . ?
C3 C2 H2B 110.4 . . ?
C2 C3 Br1 107.6(3) . . ?
C2 C3 C4 102.9(4) . . ?
C2 C3 C17 117.0(4) . . ?
C4 C3 Br1 105.6(3) . . ?
C17 C3 Br1 106.7(3) . . ?
C17 C3 C4 116.2(4) . . ?
O1 C4 N1 112.3(4) . . ?
O1 C4 C3 106.2(4) . . ?
O1 C4 H4 111.6 . . ?
N1 C4 C3 103.3(3) . . ?
N1 C4 H4 111.6 . . ?
C3 C4 H4 111.6 . . ?
N2 C5 N3 114.5(4) . . ?
N2 C5 H5 111.3 . . ?
N2 C5 C8 104.0(4) . . ?
N3 C5 H5 111.3 . . ?
N3 C5 C8 104.1(4) . . ?
C8 C5 H5 111.3 . . ?
N3 C6 H6A 110.9 . . ?
N3 C6 H6B 110.9 . . ?
N3 C6 C7 104.2(4) . . ?
H6A C6 H6B 108.9 . . ?
C7 C6 H6A 110.9 . . ?
C7 C6 H6B 110.9 . . ?
C6 C7 H7 108.5 . . ?
C6 C7 C8 102.7(4) . . ?
C8 C7 H7 108.5 . . ?
C30 C7 C6 113.8(4) . . ?
C30 C7 H7 108.5 . . ?
C30 C7 C8 114.8(4) . . ?
O2 C8 C5 113.5(4) . . ?
O2 C8 C7 105.8(3) . . ?
O2 C8 C9 116.4(4) . . ?
C7 C8 C5 104.2(4) . . ?
C9 C8 C5 102.9(4) . . ?
C9 C8 C7 113.5(4) . . ?
C10 C9 C8 128.8(4) . . ?
C10 C9 C14 122.6(5) . . ?
C14 C9 C8 108.2(4) . . ?
C9 C10 H10 121.4 . . ?
C9 C10 C11 117.2(5) . . ?
C11 C10 H10 121.4 . . ?
C10 C11 Br2 118.7(4) . . ?
C12 C11 Br2 120.4(4) . . ?
C12 C11 C10 121.0(5) . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.2(5) . . ?
C14 C13 H13 120.4 . . ?
C9 C14 N2 111.1(4) . . ?
C13 C14 N2 129.8(4) . . ?
C13 C14 C9 119.1(5) . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 O1 110.7(6) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C3 120.8(4) . . ?
C22 C17 C3 121.1(5) . . ?
C22 C17 C18 118.1(5) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(5) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.3(6) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.3(5) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.8(5) . . ?
C22 C21 H21 120.1 . . ?
C17 C22 H22 119.3 . . ?
C21 C22 C17 121.3(5) . . ?
C21 C22 H22 119.3 . . ?
C24 C23 S1 119.3(5) . . ?
C24 C23 C28 120.6(6) . . ?
C28 C23 S1 120.0(4) . . ?
C23 C24 H24 120.8 . . ?
C23 C24 C25 118.4(7) . . ?
C25 C24 H24 120.8 . . ?
C24 C25 H25 118.8 . . ?
C26 C25 C24 122.5(7) . . ?
C26 C25 H25 118.8 . . ?
C25 C26 C27 118.2(7) . . ?
C25 C26 C29 120.8(8) . . ?
C27 C26 C29 121.0(9) . . ?
C26 C27 H27 119.3 . . ?
C26 C27 C28 121.4(7) . . ?
C28 C27 H27 119.3 . . ?
C23 C28 C27 118.8(6) . . ?
C23 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C7 120.1(5) . . ?
C35 C30 C7 123.0(5) . . ?
C35 C30 C31 116.9(5) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.1(7) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 119.7 . . ?
C33 C32 C31 120.6(8) . . ?
C33 C32 H32 119.7 . . ?
C32 C33 H33 120.3 . . ?
C34 C33 C32 119.3(7) . . ?
C34 C33 H33 120.3 . . ?
C33 C34 H34 119.3 . . ?
C33 C34 C35 121.4(7) . . ?
C35 C34 H34 119.3 . . ?
C30 C35 H35 119.1 . . ?
C34 C35 C30 121.7(6) . . ?
C34 C35 H35 119.1 . . ?
O2 C36 H36A 110.0 . . ?
O2 C36 H36B 110.0 . . ?
O2 C36 C37 108.4(5) . . ?
H36A C36 H36B 108.4 . . ?
C37 C36 H36A 110.0 . . ?
C37 C36 H36B 110.0 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 C38 S2 120.7(4) . . ?
C39 C38 C43 119.9(5) . . ?
C43 C38 S2 119.2(4) . . ?
C38 C39 H39 120.5 . . ?
C38 C39 C40 119.0(6) . . ?
C40 C39 H39 120.5 . . ?
C39 C40 H40 119.4 . . ?
C39 C40 C41 121.2(7) . . ?
C41 C40 H40 119.4 . . ?
C40 C41 C44 119.7(8) . . ?
C42 C41 C40 119.0(6) . . ?
C42 C41 C44 121.3(8) . . ?
C41 C42 H42 119.7 . . ?
C41 C42 C43 120.7(6) . . ?
C43 C42 H42 119.7 . . ?
C38 C43 H43 119.9 . . ?
C42 C43 C38 120.2(6) . . ?
C42 C43 H43 119.9 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.500 449.6 176.0 ?
2 0.000 0.500 0.000 449.6 176.0 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd17389
_database_code_depnum_ccdc_archive 'CCDC 1560323'
_audit_update_record             
;
2017-07-05 deposited with the CCDC.
2017-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H38 Br N3 O4 S2'
_chemical_formula_weight         804.79

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      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                   11.9360(15)
_cell_length_b                   13.1209(17)
_cell_length_c                   13.8558(16)
_cell_angle_alpha                89.702(4)
_cell_angle_beta                 84.883(3)
_cell_angle_gamma                66.690(3)
_cell_volume                     1983.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1694
_cell_measurement_theta_min      4.535
_cell_measurement_theta_max      40.540

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.187
_shelx_estimated_absorpt_T_min   0.797
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6340
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            11488
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.691
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7361
_reflns_number_gt                3848
_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 SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1034P)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         7361
_refine_ls_number_parameters     480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1878
_refine_ls_wR_factor_gt          0.1505
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.925
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.001

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 0.61131(6) 0.28799(6) 0.47371(4) 0.1199(3) Uani 1 1 d . . . . .
S1 S 0.73511(12) 0.58177(12) 0.76864(10) 0.0842(4) Uani 1 1 d . . . . .
S2 S 1.24837(8) -0.09899(8) 0.97433(7) 0.0525(3) Uani 1 1 d . . . . .
N1 N 0.7863(3) 0.3253(3) 0.8068(2) 0.0615(9) Uani 1 1 d . . . . .
N2 N 0.6462(3) 0.5198(3) 0.8093(3) 0.0764(11) Uani 1 1 d . . . . .
N3 N 1.2480(3) 0.0004(3) 0.9036(2) 0.0502(8) Uani 1 1 d . . . . .
O1 O 0.8343(3) 0.5479(4) 0.8283(3) 0.1163(14) Uani 1 1 d . . . . .
O2 O 0.6571(4) 0.6949(3) 0.7620(3) 0.1155(14) Uani 1 1 d . . . . .
O3 O 1.1372(2) -0.1126(2) 0.96226(19) 0.0625(7) Uani 1 1 d . . . . .
O4 O 1.3635(2) -0.1893(2) 0.9527(2) 0.0684(8) Uani 1 1 d . . . . .
C1 C 0.8978(3) 0.2658(4) 0.8408(3) 0.0607(11) Uani 1 1 d . . . . .
H1 H 0.9205 0.2806 0.8999 0.073 Uiso 1 1 calc R U . . .
C2 C 0.9703(3) 0.1831(3) 0.7774(3) 0.0541(10) Uani 1 1 d . . . . .
C3 C 0.8998(4) 0.1905(3) 0.6974(3) 0.0560(10) Uani 1 1 d . . . . .
C4 C 0.7854(4) 0.2791(3) 0.7190(3) 0.0585(11) Uani 1 1 d . . . . .
C5 C 0.6969(4) 0.3082(4) 0.6530(3) 0.0649(12) Uani 1 1 d . . . . .
H5 H 0.6208 0.3663 0.6664 0.078 Uiso 1 1 calc R U . . .
C6 C 0.7272(4) 0.2476(4) 0.5676(3) 0.0736(13) Uani 1 1 d . . . . .
C7 C 0.8388(5) 0.1606(4) 0.5447(3) 0.0817(15) Uani 1 1 d . . . . .
H7 H 0.8551 0.1220 0.4855 0.098 Uiso 1 1 calc R U . . .
C8 C 0.9250(4) 0.1316(4) 0.6092(3) 0.0706(13) Uani 1 1 d . . . . .
H8 H 1.0004 0.0729 0.5944 0.085 Uiso 1 1 calc R U . . .
C9 C 1.0970(3) 0.0973(3) 0.7866(3) 0.0556(10) Uani 1 1 d . . . . .
H9 H 1.0969 0.0249 0.7698 0.067 Uiso 1 1 calc R U . . .
C10 C 1.1301(3) 0.0931(3) 0.8911(3) 0.0502(9) Uani 1 1 d . . . . .
H10A H 1.1350 0.1625 0.9088 0.060 Uiso 1 1 calc R U . . .
H10B H 1.0659 0.0846 0.9342 0.060 Uiso 1 1 calc R U . . .
C11 C 1.1934(4) 0.1138(5) 0.7188(3) 0.0719(14) Uani 1 1 d . . . . .
C12 C 1.2786(5) 0.0275(6) 0.6638(4) 0.108(2) Uani 1 1 d . . . . .
H12 H 1.2737 -0.0415 0.6633 0.130 Uiso 1 1 calc R U . . .
C13 C 1.3734(7) 0.0437(11) 0.6081(5) 0.163(5) Uani 1 1 d . . . . .
H13 H 1.4319 -0.0160 0.5717 0.196 Uiso 1 1 calc R U . . .
C14 C 1.3831(9) 0.1410(13) 0.6052(7) 0.174(6) Uani 1 1 d . . . . .
H14 H 1.4480 0.1492 0.5684 0.209 Uiso 1 1 calc R U . . .
C15 C 1.2963(8) 0.2278(9) 0.6570(7) 0.172(5) Uani 1 1 d . . . . .
H15 H 1.2998 0.2973 0.6544 0.206 Uiso 1 1 calc R U . . .
C16 C 1.2004(5) 0.2137(6) 0.7148(5) 0.109(2) Uani 1 1 d . . . . .
H16 H 1.1415 0.2739 0.7505 0.131 Uiso 1 1 calc R U . . .
C17 C 1.3565(3) 0.0279(4) 0.9003(3) 0.0588(11) Uani 1 1 d . . . . .
H17A H 1.4276 -0.0394 0.9093 0.071 Uiso 1 1 calc R U . . .
H17B H 1.3692 0.0542 0.8364 0.071 Uiso 1 1 calc R U . . .
C18 C 1.3486(4) 0.1106(4) 0.9719(3) 0.0646(12) Uani 1 1 d . . . . .
C19 C 1.3388(5) 0.1760(5) 1.0317(5) 0.0954(17) Uani 1 1 d . . . . .
H19 H 1.3309 0.2283 1.0796 0.114 Uiso 1 1 calc R U . . .
C20 C 0.6879(4) 0.4146(4) 0.8620(3) 0.0706(13) Uani 1 1 d . . . . .
H20 H 0.7165 0.4267 0.9234 0.085 Uiso 1 1 calc R U . . .
C21 C 0.5694(4) 0.3952(4) 0.8837(3) 0.0739(13) Uani 1 1 d . . . . .
H21A H 0.5736 0.3307 0.8473 0.089 Uiso 1 1 calc R U . . .
H21B H 0.5557 0.3840 0.9522 0.089 Uiso 1 1 calc R U . . .
C22 C 0.4683(4) 0.4993(4) 0.8527(3) 0.0587(11) Uani 1 1 d . . . . .
C23 C 0.5170(4) 0.5650(4) 0.8106(3) 0.0678(12) Uani 1 1 d . . . . .
H23 H 0.4715 0.6330 0.7849 0.081 Uiso 1 1 calc R U . . .
C24 C 0.3394(4) 0.5194(4) 0.8694(3) 0.0594(11) Uani 1 1 d . . . . .
C25 C 0.3036(5) 0.4343(5) 0.8941(4) 0.0901(16) Uani 1 1 d . . . . .
H25 H 0.3629 0.3632 0.8998 0.108 Uiso 1 1 calc R U . . .
C26 C 0.1804(6) 0.4529(6) 0.9107(5) 0.1085(19) Uani 1 1 d . . . . .
H26 H 0.1577 0.3944 0.9272 0.130 Uiso 1 1 calc R U . . .
C27 C 0.0929(5) 0.5567(6) 0.9026(4) 0.0970(18) Uani 1 1 d . . . . .
H27 H 0.0105 0.5686 0.9119 0.116 Uiso 1 1 calc R U . . .
C28 C 0.1252(4) 0.6435(5) 0.8812(4) 0.0844(15) Uani 1 1 d . . . . .
H28 H 0.0652 0.7149 0.8785 0.101 Uiso 1 1 calc R U . . .
C29 C 0.2472(4) 0.6248(4) 0.8634(3) 0.0687(12) Uani 1 1 d . . . . .
H29 H 0.2686 0.6839 0.8471 0.082 Uiso 1 1 calc R U . . .
C30 C 0.7928(4) 0.5248(4) 0.6515(3) 0.0708(12) Uani 1 1 d . . . . .
C31 C 0.7185(5) 0.5600(5) 0.5779(4) 0.0964(17) Uani 1 1 d . . . . .
H31 H 0.6413 0.6173 0.5889 0.116 Uiso 1 1 calc R U . . .
C32 C 0.7592(8) 0.5099(6) 0.4883(5) 0.114(2) Uani 1 1 d . . . . .
H32 H 0.7072 0.5322 0.4390 0.136 Uiso 1 1 calc R U . . .
C33 C 0.8745(8) 0.4275(6) 0.4679(4) 0.112(2) Uani 1 1 d . . . . .
C34 C 0.9489(6) 0.3967(5) 0.5434(4) 0.0984(18) Uani 1 1 d . . . . .
H34 H 1.0281 0.3428 0.5318 0.118 Uiso 1 1 calc R U . . .
C35 C 0.9088(4) 0.4437(4) 0.6339(4) 0.0801(14) Uani 1 1 d . . . . .
H35 H 0.9597 0.4209 0.6838 0.096 Uiso 1 1 calc R U . . .
C36 C 0.9208(9) 0.3707(7) 0.3697(5) 0.188(4) Uani 1 1 d . . . . .
H36A H 1.0087 0.3408 0.3626 0.282 Uiso 1 1 calc R U . . .
H36B H 0.8898 0.4234 0.3203 0.282 Uiso 1 1 calc R U . . .
H36C H 0.8933 0.3117 0.3635 0.282 Uiso 1 1 calc R U . . .
C37 C 1.2423(4) -0.0521(3) 1.0939(3) 0.0539(10) Uani 1 1 d . . . . .
C38 C 1.3486(4) -0.0850(4) 1.1391(3) 0.0684(12) Uani 1 1 d . . . . .
H38 H 1.4220 -0.1359 1.1088 0.082 Uiso 1 1 calc R U . . .
C39 C 1.3440(5) -0.0408(5) 1.2306(4) 0.0863(16) Uani 1 1 d . . . . .
H39 H 1.4155 -0.0635 1.2617 0.104 Uiso 1 1 calc R U . . .
C40 C 1.2381(6) 0.0350(5) 1.2766(3) 0.0858(15) Uani 1 1 d . . . . .
C41 C 1.1325(5) 0.0649(5) 1.2303(3) 0.0835(15) Uani 1 1 d . . . . .
H41 H 1.0588 0.1150 1.2611 0.100 Uiso 1 1 calc R U . . .
C42 C 1.1339(4) 0.0222(4) 1.1394(3) 0.0641(11) Uani 1 1 d . . . . .
H42 H 1.0620 0.0435 1.1090 0.077 Uiso 1 1 calc R U . . .
C43 C 1.2361(7) 0.0851(6) 1.3759(4) 0.135(3) Uani 1 1 d . . . . .
H43A H 1.2910 0.0295 1.4141 0.202 Uiso 1 1 calc R U . . .
H43B H 1.1545 0.1115 1.4078 0.202 Uiso 1 1 calc R U . . .
H43C H 1.2615 0.1458 1.3684 0.202 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C6 1.902(4) . ?
S1 O2 1.414(4) . ?
S1 O1 1.427(4) . ?
S1 N2 1.635(4) . ?
S1 C30 1.753(5) . ?
S2 O4 1.422(3) . ?
S2 O3 1.432(3) . ?
S2 N3 1.626(3) . ?
S2 C37 1.755(4) . ?
N1 C4 1.365(5) . ?
N1 C1 1.374(5) . ?
N1 C20 1.448(5) . ?
N2 C23 1.415(5) . ?
N2 C20 1.483(6) . ?
N3 C17 1.472(5) . ?
N3 C10 1.475(4) . ?
C1 C2 1.352(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.431(5) . ?
C2 C9 1.502(5) . ?
C3 C8 1.393(6) . ?
C3 C4 1.407(5) . ?
C4 C5 1.396(5) . ?
C5 C6 1.367(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(6) . ?
C7 C8 1.361(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C11 1.502(6) . ?
C9 C10 1.529(5) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.346(8) . ?
C11 C12 1.362(7) . ?
C12 C13 1.397(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.326(14) . ?
C13 H13 0.9300 . ?
C14 C15 1.352(14) . ?
C14 H14 0.9300 . ?
C15 C16 1.411(9) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.443(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.161(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.538(6) . ?
C20 H20 0.9800 . ?
C21 C22 1.512(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.324(6) . ?
C22 C24 1.452(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.375(7) . ?
C24 C29 1.393(6) . ?
C25 C26 1.391(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.361(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.362(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.377(6) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 C31 1.367(6) . ?
C30 C35 1.373(6) . ?
C31 C32 1.364(8) . ?
C31 H31 0.9300 . ?
C32 C33 1.378(9) . ?
C32 H32 0.9300 . ?
C33 C34 1.387(9) . ?
C33 C36 1.504(9) . ?
C34 C35 1.360(7) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C42 1.373(6) . ?
C37 C38 1.376(5) . ?
C38 C39 1.384(7) . ?
C38 H38 0.9300 . ?
C39 C40 1.365(7) . ?
C39 H39 0.9300 . ?
C40 C41 1.380(7) . ?
C40 C43 1.521(7) . ?
C41 C42 1.378(6) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 121.4(3) . . ?
O2 S1 N2 105.7(2) . . ?
O1 S1 N2 106.1(2) . . ?
O2 S1 C30 109.0(2) . . ?
O1 S1 C30 108.3(2) . . ?
N2 S1 C30 105.2(2) . . ?
O4 S2 O3 120.07(18) . . ?
O4 S2 N3 106.66(17) . . ?
O3 S2 N3 105.75(16) . . ?
O4 S2 C37 107.75(18) . . ?
O3 S2 C37 108.72(17) . . ?
N3 S2 C37 107.24(18) . . ?
C4 N1 C1 107.7(3) . . ?
C4 N1 C20 128.7(3) . . ?
C1 N1 C20 123.4(3) . . ?
C23 N2 C20 109.8(4) . . ?
C23 N2 S1 125.2(3) . . ?
C20 N2 S1 124.5(3) . . ?
C17 N3 C10 116.5(3) . . ?
C17 N3 S2 116.3(2) . . ?
C10 N3 S2 118.6(2) . . ?
C2 C1 N1 111.5(3) . . ?
C2 C1 H1 124.3 . . ?
N1 C1 H1 124.3 . . ?
C1 C2 C3 105.6(3) . . ?
C1 C2 C9 129.1(3) . . ?
C3 C2 C9 125.3(4) . . ?
C8 C3 C4 119.7(4) . . ?
C8 C3 C2 133.1(4) . . ?
C4 C3 C2 107.2(3) . . ?
N1 C4 C5 131.4(4) . . ?
N1 C4 C3 108.0(3) . . ?
C5 C4 C3 120.6(4) . . ?
C6 C5 C4 117.0(4) . . ?
C6 C5 H5 121.5 . . ?
C4 C5 H5 121.5 . . ?
C5 C6 C7 123.4(4) . . ?
C5 C6 Br1 118.4(3) . . ?
C7 C6 Br1 118.2(3) . . ?
C8 C7 C6 119.7(4) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C3 119.6(4) . . ?
C7 C8 H8 120.2 . . ?
C3 C8 H8 120.2 . . ?
C2 C9 C11 113.1(3) . . ?
C2 C9 C10 111.1(3) . . ?
C11 C9 C10 110.2(3) . . ?
C2 C9 H9 107.4 . . ?
C11 C9 H9 107.4 . . ?
C10 C9 H9 107.4 . . ?
N3 C10 C9 111.6(3) . . ?
N3 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N3 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C16 C11 C12 118.8(5) . . ?
C16 C11 C9 120.2(5) . . ?
C12 C11 C9 121.0(6) . . ?
C11 C12 C13 119.3(8) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 122.6(10) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C13 C14 C15 118.2(10) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C14 C15 C16 120.5(10) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 120.5(7) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 N3 114.6(3) . . ?
C18 C17 H17A 108.6 . . ?
N3 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
N3 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 177.2(5) . . ?
C18 C19 H19 180.0 . . ?
N1 C20 N2 112.3(4) . . ?
N1 C20 C21 114.6(4) . . ?
N2 C20 C21 102.8(3) . . ?
N1 C20 H20 108.9 . . ?
N2 C20 H20 108.9 . . ?
C21 C20 H20 108.9 . . ?
C22 C21 C20 105.3(4) . . ?
C22 C21 H21A 110.7 . . ?
C20 C21 H21A 110.7 . . ?
C22 C21 H21B 110.7 . . ?
C20 C21 H21B 110.7 . . ?
H21A C21 H21B 108.8 . . ?
C23 C22 C24 127.7(4) . . ?
C23 C22 C21 109.4(4) . . ?
C24 C22 C21 123.0(4) . . ?
C22 C23 N2 112.1(4) . . ?
C22 C23 H23 123.9 . . ?
N2 C23 H23 123.9 . . ?
C25 C24 C29 117.3(4) . . ?
C25 C24 C22 120.7(4) . . ?
C29 C24 C22 122.0(4) . . ?
C24 C25 C26 121.1(5) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C27 C26 C25 119.9(6) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C28 C27 C26 120.5(5) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 119.6(5) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C28 C29 C24 121.6(5) . . ?
C28 C29 H29 119.2 . . ?
C24 C29 H29 119.2 . . ?
C31 C30 C35 120.3(5) . . ?
C31 C30 S1 118.7(4) . . ?
C35 C30 S1 121.0(4) . . ?
C30 C31 C32 119.1(6) . . ?
C30 C31 H31 120.5 . . ?
C32 C31 H31 120.5 . . ?
C31 C32 C33 122.4(6) . . ?
C31 C32 H32 118.8 . . ?
C33 C32 H32 118.8 . . ?
C34 C33 C32 116.9(6) . . ?
C34 C33 C36 119.9(8) . . ?
C32 C33 C36 123.2(8) . . ?
C35 C34 C33 121.5(6) . . ?
C35 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C34 C35 C30 119.8(5) . . ?
C34 C35 H35 120.1 . . ?
C30 C35 H35 120.1 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C42 C37 C38 120.4(4) . . ?
C42 C37 S2 120.1(3) . . ?
C38 C37 S2 119.4(3) . . ?
C37 C38 C39 118.7(4) . . ?
C37 C38 H38 120.6 . . ?
C39 C38 H38 120.6 . . ?
C40 C39 C38 122.1(4) . . ?
C40 C39 H39 118.9 . . ?
C38 C39 H39 118.9 . . ?
C39 C40 C41 117.9(4) . . ?
C39 C40 C43 121.2(5) . . ?
C41 C40 C43 120.9(6) . . ?
C40 C41 C42 121.3(5) . . ?
C40 C41 H41 119.3 . . ?
C42 C41 H41 119.3 . . ?
C37 C42 C41 119.5(4) . . ?
C37 C42 H42 120.3 . . ?
C41 C42 H42 120.3 . . ?
C40 C43 H43A 109.5 . . ?
C40 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C40 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N2 C23 15.7(5) . . . . ?
O1 S1 N2 C23 145.8(4) . . . . ?
C30 S1 N2 C23 -99.5(4) . . . . ?
O2 S1 N2 C20 -155.7(4) . . . . ?
O1 S1 N2 C20 -25.5(4) . . . . ?
C30 S1 N2 C20 89.1(4) . . . . ?
O4 S2 N3 C17 -49.0(3) . . . . ?
O3 S2 N3 C17 -177.9(3) . . . . ?
C37 S2 N3 C17 66.2(3) . . . . ?
O4 S2 N3 C10 164.2(3) . . . . ?
O3 S2 N3 C10 35.3(3) . . . . ?
C37 S2 N3 C10 -80.6(3) . . . . ?
C4 N1 C1 C2 0.8(5) . . . . ?
C20 N1 C1 C2 176.3(4) . . . . ?
N1 C1 C2 C3 -0.1(5) . . . . ?
N1 C1 C2 C9 -178.4(4) . . . . ?
C1 C2 C3 C8 177.5(5) . . . . ?
C9 C2 C3 C8 -4.1(8) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C9 C2 C3 C4 177.7(4) . . . . ?
C1 N1 C4 C5 -178.3(4) . . . . ?
C20 N1 C4 C5 6.4(8) . . . . ?
C1 N1 C4 C3 -1.2(5) . . . . ?
C20 N1 C4 C3 -176.4(4) . . . . ?
C8 C3 C4 N1 -177.3(4) . . . . ?
C2 C3 C4 N1 1.1(5) . . . . ?
C8 C3 C4 C5 0.2(7) . . . . ?
C2 C3 C4 C5 178.7(4) . . . . ?
N1 C4 C5 C6 176.5(5) . . . . ?
C3 C4 C5 C6 -0.4(7) . . . . ?
C4 C5 C6 C7 0.1(8) . . . . ?
C4 C5 C6 Br1 -177.8(3) . . . . ?
C5 C6 C7 C8 0.2(8) . . . . ?
Br1 C6 C7 C8 178.2(4) . . . . ?
C6 C7 C8 C3 -0.3(8) . . . . ?
C4 C3 C8 C7 0.1(7) . . . . ?
C2 C3 C8 C7 -177.8(5) . . . . ?
C1 C2 C9 C11 -110.4(5) . . . . ?
C3 C2 C9 C11 71.6(6) . . . . ?
C1 C2 C9 C10 14.1(6) . . . . ?
C3 C2 C9 C10 -163.9(4) . . . . ?
C17 N3 C10 C9 97.7(4) . . . . ?
S2 N3 C10 C9 -115.6(3) . . . . ?
C2 C9 C10 N3 173.2(3) . . . . ?
C11 C9 C10 N3 -60.6(5) . . . . ?
C2 C9 C11 C16 51.0(6) . . . . ?
C10 C9 C11 C16 -74.0(5) . . . . ?
C2 C9 C11 C12 -132.2(4) . . . . ?
C10 C9 C11 C12 102.8(5) . . . . ?
C16 C11 C12 C13 2.6(8) . . . . ?
C9 C11 C12 C13 -174.3(5) . . . . ?
C11 C12 C13 C14 -1.1(12) . . . . ?
C12 C13 C14 C15 -1.2(15) . . . . ?
C13 C14 C15 C16 2.0(14) . . . . ?
C12 C11 C16 C15 -1.9(8) . . . . ?
C9 C11 C16 C15 175.1(5) . . . . ?
C14 C15 C16 C11 -0.5(11) . . . . ?
C10 N3 C17 C18 58.4(4) . . . . ?
S2 N3 C17 C18 -89.1(4) . . . . ?
C4 N1 C20 N2 -61.4(6) . . . . ?
C1 N1 C20 N2 124.0(4) . . . . ?
C4 N1 C20 C21 55.5(6) . . . . ?
C1 N1 C20 C21 -119.1(4) . . . . ?
C23 N2 C20 N1 130.6(4) . . . . ?
S1 N2 C20 N1 -56.9(5) . . . . ?
C23 N2 C20 C21 6.9(5) . . . . ?
S1 N2 C20 C21 179.4(3) . . . . ?
N1 C20 C21 C22 -129.4(4) . . . . ?
N2 C20 C21 C22 -7.2(5) . . . . ?
C20 C21 C22 C23 5.5(5) . . . . ?
C20 C21 C22 C24 -174.0(4) . . . . ?
C24 C22 C23 N2 178.3(4) . . . . ?
C21 C22 C23 N2 -1.2(5) . . . . ?
C20 N2 C23 C22 -3.9(5) . . . . ?
S1 N2 C23 C22 -176.3(3) . . . . ?
C23 C22 C24 C25 165.4(5) . . . . ?
C21 C22 C24 C25 -15.1(7) . . . . ?
C23 C22 C24 C29 -16.0(7) . . . . ?
C21 C22 C24 C29 163.4(4) . . . . ?
C29 C24 C25 C26 1.1(8) . . . . ?
C22 C24 C25 C26 179.7(5) . . . . ?
C24 C25 C26 C27 -0.1(9) . . . . ?
C25 C26 C27 C28 -1.9(9) . . . . ?
C26 C27 C28 C29 2.8(8) . . . . ?
C27 C28 C29 C24 -1.8(7) . . . . ?
C25 C24 C29 C28 -0.2(7) . . . . ?
C22 C24 C29 C28 -178.8(4) . . . . ?
O2 S1 C30 C31 -35.9(5) . . . . ?
O1 S1 C30 C31 -169.8(4) . . . . ?
N2 S1 C30 C31 77.1(5) . . . . ?
O2 S1 C30 C35 146.3(4) . . . . ?
O1 S1 C30 C35 12.4(5) . . . . ?
N2 S1 C30 C35 -100.7(4) . . . . ?
C35 C30 C31 C32 2.9(8) . . . . ?
S1 C30 C31 C32 -174.9(5) . . . . ?
C30 C31 C32 C33 -2.3(10) . . . . ?
C31 C32 C33 C34 0.0(10) . . . . ?
C31 C32 C33 C36 179.6(6) . . . . ?
C32 C33 C34 C35 1.7(10) . . . . ?
C36 C33 C34 C35 -177.8(6) . . . . ?
C33 C34 C35 C30 -1.1(9) . . . . ?
C31 C30 C35 C34 -1.3(8) . . . . ?
S1 C30 C35 C34 176.5(4) . . . . ?
O4 S2 C37 C42 -169.1(3) . . . . ?
O3 S2 C37 C42 -37.5(4) . . . . ?
N3 S2 C37 C42 76.4(4) . . . . ?
O4 S2 C37 C38 15.0(4) . . . . ?
O3 S2 C37 C38 146.6(3) . . . . ?
N3 S2 C37 C38 -99.5(4) . . . . ?
C42 C37 C38 C39 -0.7(6) . . . . ?
S2 C37 C38 C39 175.2(4) . . . . ?
C37 C38 C39 C40 -0.7(8) . . . . ?
C38 C39 C40 C41 1.9(8) . . . . ?
C38 C39 C40 C43 -178.1(5) . . . . ?
C39 C40 C41 C42 -1.7(8) . . . . ?
C43 C40 C41 C42 178.3(5) . . . . ?
C38 C37 C42 C41 0.9(7) . . . . ?
S2 C37 C42 C41 -174.9(4) . . . . ?
C40 C41 C42 C37 0.3(8) . . . . ?

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-4

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

data_cd17318
_database_code_depnum_ccdc_archive 'CCDC 1552681'
_audit_update_record             
;
2017-05-27 deposited with the CCDC.
2017-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H26 N2 O2 S'
_chemical_formula_weight         490.60

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

_space_group_crystal_system      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                   10.688(2)
_cell_length_b                   10.745(2)
_cell_length_c                   11.245(2)
_cell_angle_alpha                103.535(4)
_cell_angle_beta                 94.412(4)
_cell_angle_gamma                96.045(4)
_cell_volume                     1241.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1885
_cell_measurement_theta_min      4.722
_cell_measurement_theta_max      48.099

_exptl_crystal_description       prismatic
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6561
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            7170
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.873
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4618
_reflns_number_gt                3563
_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 SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0916P)²+0.0908P] 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         4618
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1554
_refine_ls_wR_factor_gt          0.1430
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.006
_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
S1 S 0.68435(6) 0.86149(6) 0.92499(5) 0.0367(2) Uani 1 1 d . . . . .
N1 N 0.59050(18) 0.81701(18) 0.79728(17) 0.0364(5) Uani 1 1 d . . . . .
N2 N 0.63184(17) 0.60658(17) 0.68354(18) 0.0364(5) Uani 1 1 d . . . . .
O1 O 0.75841(17) 0.76000(16) 0.92612(16) 0.0474(5) Uani 1 1 d . . . . .
O2 O 0.60548(17) 0.89966(17) 1.01996(15) 0.0476(5) Uani 1 1 d . . . . .
C1 C 0.6311(2) 0.7405(2) 0.6813(2) 0.0332(5) Uani 1 1 d . . . . .
H1 H 0.7165 0.7769 0.6711 0.040 Uiso 1 1 calc R U . . .
C2 C 0.5369(2) 0.7646(2) 0.5814(2) 0.0375(5) Uani 1 1 d . . . . .
H2A H 0.5812 0.7930 0.5184 0.045 Uiso 1 1 calc R U . . .
H2B H 0.4799 0.6867 0.5432 0.045 Uiso 1 1 calc R U . . .
C3 C 0.4655(2) 0.8685(2) 0.6478(2) 0.0324(5) Uani 1 1 d . . . . .
C4 C 0.4997(2) 0.8936(2) 0.7672(2) 0.0346(5) Uani 1 1 d . . . . .
H4 H 0.4673 0.9553 0.8251 0.041 Uiso 1 1 calc R U . . .
C5 C 0.3691(2) 0.9251(2) 0.5865(2) 0.0340(5) Uani 1 1 d . . . . .
C6 C 0.3431(2) 0.8885(2) 0.4597(2) 0.0398(6) Uani 1 1 d . . . . .
H6 H 0.3899 0.8300 0.4138 0.048 Uiso 1 1 calc R U . . .
C7 C 0.2491(3) 0.9371(3) 0.4003(2) 0.0489(7) Uani 1 1 d . . . . .
H7 H 0.2328 0.9105 0.3151 0.059 Uiso 1 1 calc R U . . .
C8 C 0.1798(3) 1.0238(3) 0.4653(3) 0.0524(7) Uani 1 1 d . . . . .
H8 H 0.1154 1.0554 0.4252 0.063 Uiso 1 1 calc R U . . .
C9 C 0.2065(3) 1.0640(3) 0.5910(3) 0.0579(8) Uani 1 1 d . . . . .
H9 H 0.1612 1.1248 0.6358 0.070 Uiso 1 1 calc R U . . .
C10 C 0.2990(3) 1.0153(3) 0.6510(2) 0.0506(7) Uani 1 1 d . . . . .
H10 H 0.3151 1.0430 0.7361 0.061 Uiso 1 1 calc R U . . .
C11 C 0.5373(2) 0.5356(2) 0.7270(2) 0.0407(6) Uani 1 1 d . . . . .
C12 C 0.4135(2) 0.5575(3) 0.7438(3) 0.0540(7) Uani 1 1 d . . . . .
H12 H 0.3808 0.6275 0.7234 0.065 Uiso 1 1 calc R U . . .
C13 C 0.3410(3) 0.4719(3) 0.7918(3) 0.0673(9) Uani 1 1 d . . . . .
H13 H 0.2577 0.4842 0.8044 0.081 Uiso 1 1 calc R U . . .
C14 C 0.3902(3) 0.3671(3) 0.8218(3) 0.0732(10) Uani 1 1 d . . . . .
H14 H 0.3389 0.3109 0.8545 0.088 Uiso 1 1 calc R U . . .
C15 C 0.5112(3) 0.3443(3) 0.8048(3) 0.0622(8) Uani 1 1 d . . . . .
H15 H 0.5421 0.2732 0.8246 0.075 Uiso 1 1 calc R U . . .
C16 C 0.5881(2) 0.4305(2) 0.7569(2) 0.0462(6) Uani 1 1 d . . . . .
C17 C 0.7168(2) 0.4407(2) 0.7309(2) 0.0473(6) Uani 1 1 d . . . . .
H17 H 0.7739 0.3833 0.7405 0.057 Uiso 1 1 calc R U . . .
C18 C 0.7411(2) 0.5479(2) 0.6901(2) 0.0365(5) Uani 1 1 d . . . . .
C19 C 0.8592(2) 0.6026(2) 0.6519(2) 0.0392(6) Uani 1 1 d . . . . .
C20 C 0.8645(3) 0.6235(3) 0.5357(3) 0.0538(7) Uani 1 1 d . . . . .
H20 H 0.7918 0.6044 0.4805 0.065 Uiso 1 1 calc R U . . .
C21 C 0.9765(3) 0.6723(3) 0.5009(3) 0.0663(9) Uani 1 1 d . . . . .
H21 H 0.9794 0.6845 0.4219 0.080 Uiso 1 1 calc R U . . .
C22 C 1.0835(3) 0.7028(3) 0.5823(4) 0.0754(10) Uani 1 1 d . . . . .
H22 H 1.1588 0.7368 0.5589 0.090 Uiso 1 1 calc R U . . .
C23 C 1.0799(3) 0.6832(3) 0.6987(3) 0.0706(9) Uani 1 1 d . . . . .
H23 H 1.1527 0.7039 0.7539 0.085 Uiso 1 1 calc R U . . .
C24 C 0.9689(3) 0.6331(3) 0.7331(3) 0.0540(7) Uani 1 1 d . . . . .
H24 H 0.9670 0.6195 0.8116 0.065 Uiso 1 1 calc R U . . .
C25 C 0.7848(2) 0.9988(2) 0.9169(2) 0.0380(6) Uani 1 1 d . . . . .
C26 C 0.9002(2) 0.9844(2) 0.8714(2) 0.0435(6) Uani 1 1 d . . . . .
H26 H 0.9252 0.9028 0.8465 0.052 Uiso 1 1 calc R U . . .
C27 C 0.9775(2) 1.0916(3) 0.8632(2) 0.0497(7) Uani 1 1 d . . . . .
H27 H 1.0551 1.0817 0.8323 0.060 Uiso 1 1 calc R U . . .
C28 C 0.9430(3) 1.2139(3) 0.8996(2) 0.0495(7) Uani 1 1 d . . . . .
C29 C 0.8275(3) 1.2268(3) 0.9454(2) 0.0533(7) Uani 1 1 d . . . . .
H29 H 0.8029 1.3086 0.9703 0.064 Uiso 1 1 calc R U . . .
C30 C 0.7482(3) 1.1207(2) 0.9549(2) 0.0480(6) Uani 1 1 d . . . . .
H30 H 0.6709 1.1307 0.9864 0.058 Uiso 1 1 calc R U . . .
C31 C 1.0286(3) 1.3306(3) 0.8878(3) 0.0716(9) Uani 1 1 d . . . . .
H31A H 1.0940 1.3547 0.9554 0.107 Uiso 1 1 calc R U . . .
H31B H 0.9801 1.4011 0.8886 0.107 Uiso 1 1 calc R U . . .
H31C H 1.0662 1.3104 0.8119 0.107 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4151(17) . ?
S1 O2 1.4233(17) . ?
S1 N1 1.6289(19) . ?
S1 C25 1.755(3) . ?
N1 C4 1.408(3) . ?
N1 C1 1.492(3) . ?
N2 C11 1.389(3) . ?
N2 C18 1.389(3) . ?
N2 C1 1.446(3) . ?
C1 C2 1.536(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.504(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.320(3) . ?
C3 C5 1.458(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 C10 1.391(3) . ?
C6 C7 1.377(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.365(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.388(3) . ?
C11 C16 1.401(3) . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.402(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.427(4) . ?
C17 C18 1.344(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.473(3) . ?
C19 C20 1.380(4) . ?
C19 C24 1.389(4) . ?
C20 C21 1.378(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.376(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.372(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.381(3) . ?
C25 C30 1.387(3) . ?
C26 C27 1.371(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.380(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.382(4) . ?
C28 C31 1.511(4) . ?
C29 C30 1.377(4) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.58(11) . . ?
O1 S1 N1 106.20(10) . . ?
O2 S1 N1 105.94(10) . . ?
O1 S1 C25 108.37(12) . . ?
O2 S1 C25 107.86(11) . . ?
N1 S1 C25 107.19(11) . . ?
C4 N1 C1 108.83(17) . . ?
C4 N1 S1 121.84(15) . . ?
C1 N1 S1 122.09(15) . . ?
C11 N2 C18 107.78(19) . . ?
C11 N2 C1 123.88(18) . . ?
C18 N2 C1 123.98(19) . . ?
N2 C1 N1 111.37(18) . . ?
N2 C1 C2 115.02(18) . . ?
N1 C1 C2 103.00(16) . . ?
N2 C1 H1 109.1 . . ?
N1 C1 H1 109.1 . . ?
C2 C1 H1 109.1 . . ?
C3 C2 C1 105.00(18) . . ?
C3 C2 H2A 110.7 . . ?
C1 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
C1 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
C4 C3 C5 126.8(2) . . ?
C4 C3 C2 109.5(2) . . ?
C5 C3 C2 123.59(19) . . ?
C3 C4 N1 112.75(19) . . ?
C3 C4 H4 123.6 . . ?
N1 C4 H4 123.6 . . ?
C6 C5 C10 117.4(2) . . ?
C6 C5 C3 120.2(2) . . ?
C10 C5 C3 122.4(2) . . ?
C7 C6 C5 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 119.1(2) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C5 121.0(2) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C12 C11 N2 130.1(2) . . ?
C12 C11 C16 122.1(2) . . ?
N2 C11 C16 107.8(2) . . ?
C13 C12 C11 117.5(3) . . ?
C13 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
C12 C13 C14 121.0(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 121.9(3) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C16 118.5(3) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C11 C16 C15 118.9(2) . . ?
C11 C16 C17 106.6(2) . . ?
C15 C16 C17 134.4(2) . . ?
C18 C17 C16 108.0(2) . . ?
C18 C17 H17 126.0 . . ?
C16 C17 H17 126.0 . . ?
C17 C18 N2 109.7(2) . . ?
C17 C18 C19 129.7(2) . . ?
N2 C18 C19 120.6(2) . . ?
C20 C19 C24 118.5(3) . . ?
C20 C19 C18 121.5(2) . . ?
C24 C19 C18 120.0(2) . . ?
C21 C20 C19 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.1(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 119.9(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C19 120.7(3) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
C26 C25 C30 120.2(2) . . ?
C26 C25 S1 119.48(18) . . ?
C30 C25 S1 120.3(2) . . ?
C27 C26 C25 119.3(2) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C27 C28 121.6(3) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 H27 119.2 . . ?
C27 C28 C29 118.4(3) . . ?
C27 C28 C31 120.8(3) . . ?
C29 C28 C31 120.8(3) . . ?
C30 C29 C28 121.2(2) . . ?
C30 C29 H29 119.4 . . ?
C28 C29 H29 119.4 . . ?
C29 C30 C25 119.3(3) . . ?
C29 C30 H30 120.3 . . ?
C25 C30 H30 120.3 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C4 177.88(18) . . . . ?
O2 S1 N1 C4 48.5(2) . . . . ?
C25 S1 N1 C4 -66.4(2) . . . . ?
O1 S1 N1 C1 -35.2(2) . . . . ?
O2 S1 N1 C1 -164.55(17) . . . . ?
C25 S1 N1 C1 80.47(19) . . . . ?
C11 N2 C1 N1 42.6(3) . . . . ?
C18 N2 C1 N1 -111.0(2) . . . . ?
C11 N2 C1 C2 -74.0(3) . . . . ?
C18 N2 C1 C2 132.3(2) . . . . ?
C4 N1 C1 N2 -133.09(19) . . . . ?
S1 N1 C1 N2 76.2(2) . . . . ?
C4 N1 C1 C2 -9.3(2) . . . . ?
S1 N1 C1 C2 -159.95(16) . . . . ?
N2 C1 C2 C3 130.10(19) . . . . ?
N1 C1 C2 C3 8.7(2) . . . . ?
C1 C2 C3 C4 -5.6(3) . . . . ?
C1 C2 C3 C5 177.5(2) . . . . ?
C5 C3 C4 N1 176.5(2) . . . . ?
C2 C3 C4 N1 -0.4(3) . . . . ?
C1 N1 C4 C3 6.5(3) . . . . ?
S1 N1 C4 C3 157.21(17) . . . . ?
C4 C3 C5 C6 -179.7(2) . . . . ?
C2 C3 C5 C6 -3.2(3) . . . . ?
C4 C3 C5 C10 -0.5(4) . . . . ?
C2 C3 C5 C10 175.9(2) . . . . ?
C10 C5 C6 C7 -1.7(4) . . . . ?
C3 C5 C6 C7 177.5(2) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 C9 1.2(4) . . . . ?
C7 C8 C9 C10 -1.8(5) . . . . ?
C8 C9 C10 C5 0.6(5) . . . . ?
C6 C5 C10 C9 1.1(4) . . . . ?
C3 C5 C10 C9 -178.1(2) . . . . ?
C18 N2 C11 C12 177.0(3) . . . . ?
C1 N2 C11 C12 19.7(4) . . . . ?
C18 N2 C11 C16 -1.7(3) . . . . ?
C1 N2 C11 C16 -159.0(2) . . . . ?
N2 C11 C12 C13 -178.4(3) . . . . ?
C16 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C12 C13 C14 C15 -0.3(6) . . . . ?
C13 C14 C15 C16 0.8(5) . . . . ?
C12 C11 C16 C15 0.3(4) . . . . ?
N2 C11 C16 C15 179.1(2) . . . . ?
C12 C11 C16 C17 -178.4(2) . . . . ?
N2 C11 C16 C17 0.4(3) . . . . ?
C14 C15 C16 C11 -0.8(4) . . . . ?
C14 C15 C16 C17 177.6(3) . . . . ?
C11 C16 C17 C18 1.2(3) . . . . ?
C15 C16 C17 C18 -177.3(3) . . . . ?
C16 C17 C18 N2 -2.3(3) . . . . ?
C16 C17 C18 C19 179.5(2) . . . . ?
C11 N2 C18 C17 2.5(3) . . . . ?
C1 N2 C18 C17 159.8(2) . . . . ?
C11 N2 C18 C19 -179.1(2) . . . . ?
C1 N2 C18 C19 -21.8(3) . . . . ?
C17 C18 C19 C20 122.0(3) . . . . ?
N2 C18 C19 C20 -56.1(3) . . . . ?
C17 C18 C19 C24 -57.4(4) . . . . ?
N2 C18 C19 C24 124.6(3) . . . . ?
C24 C19 C20 C21 0.7(4) . . . . ?
C18 C19 C20 C21 -178.7(2) . . . . ?
C19 C20 C21 C22 -1.2(4) . . . . ?
C20 C21 C22 C23 0.9(5) . . . . ?
C21 C22 C23 C24 0.0(5) . . . . ?
C22 C23 C24 C19 -0.5(5) . . . . ?
C20 C19 C24 C23 0.1(4) . . . . ?
C18 C19 C24 C23 179.5(2) . . . . ?
O1 S1 C25 C26 22.2(2) . . . . ?
O2 S1 C25 C26 154.26(18) . . . . ?
N1 S1 C25 C26 -92.0(2) . . . . ?
O1 S1 C25 C30 -158.45(19) . . . . ?
O2 S1 C25 C30 -26.4(2) . . . . ?
N1 S1 C25 C30 87.3(2) . . . . ?
C30 C25 C26 C27 -0.5(3) . . . . ?
S1 C25 C26 C27 178.85(18) . . . . ?
C25 C26 C27 C28 0.2(4) . . . . ?
C26 C27 C28 C29 0.1(4) . . . . ?
C26 C27 C28 C31 -179.0(2) . . . . ?
C27 C28 C29 C30 0.1(4) . . . . ?
C31 C28 C29 C30 179.1(2) . . . . ?
C28 C29 C30 C25 -0.4(4) . . . . ?
C26 C25 C30 C29 0.6(4) . . . . ?
S1 C25 C30 C29 -178.72(19) . . . . ?

_refine_diff_density_max         0.428
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-4

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

data_cd17132
_database_code_depnum_ccdc_archive 'CCDC 1538040'
_audit_update_record             
;
2017-03-15 deposited with the CCDC.
2017-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 Br N2 O2 S'
_chemical_formula_weight         493.41

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.816(3)
_cell_length_b                   10.4010(11)
_cell_length_c                   16.9512(18)
_cell_angle_alpha                90
_cell_angle_beta                 96.192(2)
_cell_angle_gamma                90
_cell_volume                     4349.7(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2719
_cell_measurement_theta_min      4.801
_cell_measurement_theta_max      44.678

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             2016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.011
_shelx_estimated_absorpt_T_min   0.689
_shelx_estimated_absorpt_T_max   0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6232
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            12209
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.651
_diffrn_reflns_theta_max         25.499
_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             4054
_reflns_number_gt                2926
_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 SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0609P)²+0.3353P] 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         4054
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.21423(2) 0.07665(4) 0.99622(2) 0.07201(17) Uani 1 1 d . . . . .
S1 S 0.14462(3) 0.35999(8) 0.56741(4) 0.0488(2) Uani 1 1 d . . . . .
N1 N 0.08087(8) 0.3340(2) 0.72576(13) 0.0461(6) Uani 1 1 d . . . . .
N2 N 0.09788(9) 0.2637(2) 0.59329(14) 0.0497(6) Uani 1 1 d . . . . .
O1 O 0.12492(9) 0.4869(2) 0.57862(14) 0.0647(6) Uani 1 1 d . . . . .
O2 O 0.15696(8) 0.3183(2) 0.49149(12) 0.0625(6) Uani 1 1 d . . . . .
C1 C 0.11059(10) 0.2572(3) 0.78164(15) 0.0404(6) Uani 1 1 d . . . . .
C2 C 0.12863(11) 0.1310(3) 0.77683(18) 0.0512(7) Uani 1 1 d . . . . .
H2 H 0.1204 0.0826 0.7310 0.061 Uiso 1 1 calc R U . . .
C3 C 0.15857(12) 0.0808(3) 0.84134(18) 0.0523(7) Uani 1 1 d . . . . .
H3 H 0.1710 -0.0035 0.8399 0.063 Uiso 1 1 calc R U . . .
C4 C 0.17084(10) 0.1542(3) 0.90953(17) 0.0481(7) Uani 1 1 d . . . . .
C5 C 0.15346(10) 0.2776(3) 0.91637(16) 0.0453(7) Uani 1 1 d . . . . .
H5 H 0.1618 0.3242 0.9629 0.054 Uiso 1 1 calc R U . . .
C6 C 0.12259(10) 0.3312(3) 0.85061(16) 0.0417(6) Uani 1 1 d . . . . .
C7 C 0.09884(11) 0.4549(3) 0.83495(18) 0.0496(7) Uani 1 1 d . . . . .
H7 H 0.0999 0.5238 0.8700 0.060 Uiso 1 1 calc R U . . .
C8 C 0.07473(11) 0.4530(3) 0.75999(19) 0.0514(7) Uani 1 1 d . . . . .
H8 H 0.0564 0.5221 0.7347 0.062 Uiso 1 1 calc R U . . .
C9 C 0.05732(11) 0.2985(3) 0.64689(17) 0.0497(7) Uani 1 1 d . . . . .
H9 H 0.0356 0.3706 0.6238 0.060 Uiso 1 1 calc R U . . .
C10 C 0.02133(11) 0.1774(3) 0.64503(18) 0.0565(8) Uani 1 1 d . . . . .
H10A H 0.0181 0.1471 0.6984 0.068 Uiso 1 1 calc R U . . .
H10B H -0.0146 0.1957 0.6192 0.068 Uiso 1 1 calc R U . . .
C11 C 0.04920(10) 0.0790(3) 0.59904(16) 0.0465(7) Uani 1 1 d . . . . .
C12 C 0.09131(11) 0.1332(3) 0.57103(16) 0.0456(7) Uani 1 1 d . . . . .
H12 H 0.1142 0.0901 0.5400 0.055 Uiso 1 1 calc R U . . .
C13 C 0.03074(11) -0.0547(3) 0.59182(17) 0.0498(7) Uani 1 1 d . . . . .
C14 C -0.01384(14) -0.0953(4) 0.6280(2) 0.0721(10) Uani 1 1 d . . . . .
H14 H -0.0324 -0.0371 0.6567 0.087 Uiso 1 1 calc R U . . .
C15 C -0.03072(17) -0.2217(4) 0.6216(3) 0.0898(13) Uani 1 1 d . . . . .
H15 H -0.0607 -0.2475 0.6460 0.108 Uiso 1 1 calc R U . . .
C16 C -0.00427(15) -0.3091(4) 0.5804(2) 0.0790(11) Uani 1 1 d . . . . .
H16 H -0.0159 -0.3941 0.5768 0.095 Uiso 1 1 calc R U . . .
C17 C 0.03946(13) -0.2707(3) 0.5443(2) 0.0686(9) Uani 1 1 d . . . . .
H17 H 0.0580 -0.3300 0.5164 0.082 Uiso 1 1 calc R U . . .
C18 C 0.05640(12) -0.1450(3) 0.54892(19) 0.0569(8) Uani 1 1 d . . . . .
H18 H 0.0857 -0.1200 0.5227 0.068 Uiso 1 1 calc R U . . .
C19 C 0.20213(10) 0.3338(2) 0.63572(16) 0.0406(6) Uani 1 1 d . . . . .
C20 C 0.23991(12) 0.2439(3) 0.61907(18) 0.0502(7) Uani 1 1 d . . . . .
H20 H 0.2358 0.1990 0.5714 0.060 Uiso 1 1 calc R U . . .
C21 C 0.28403(12) 0.2214(3) 0.6743(2) 0.0578(8) Uani 1 1 d . . . . .
H21 H 0.3098 0.1611 0.6632 0.069 Uiso 1 1 calc R U . . .
C22 C 0.29065(12) 0.2864(3) 0.74575(19) 0.0525(7) Uani 1 1 d . . . . .
C23 C 0.25201(12) 0.3759(3) 0.76012(18) 0.0542(7) Uani 1 1 d . . . . .
H23 H 0.2558 0.4205 0.8079 0.065 Uiso 1 1 calc R U . . .
C24 C 0.20827(11) 0.4010(3) 0.70611(18) 0.0504(7) Uani 1 1 d . . . . .
H24 H 0.1830 0.4628 0.7168 0.060 Uiso 1 1 calc R U . . .
C25 C 0.33998(14) 0.2650(4) 0.8047(2) 0.0816(11) Uani 1 1 d . . . . .
H25A H 0.3565 0.3463 0.8191 0.122 Uiso 1 1 calc R U . . .
H25B H 0.3654 0.2116 0.7811 0.122 Uiso 1 1 calc R U . . .
H25C H 0.3293 0.2236 0.8511 0.122 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.905(3) . ?
S1 O2 1.422(2) . ?
S1 O1 1.427(2) . ?
S1 N2 1.628(2) . ?
S1 C19 1.759(3) . ?
N1 C8 1.382(4) . ?
N1 C1 1.389(3) . ?
N1 C9 1.448(3) . ?
N2 C12 1.414(4) . ?
N2 C9 1.472(4) . ?
C1 C2 1.393(4) . ?
C1 C6 1.404(4) . ?
C2 C3 1.358(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(4) . ?
C5 C6 1.399(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.428(4) . ?
C7 C8 1.345(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.542(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.500(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.320(4) . ?
C11 C13 1.465(4) . ?
C12 H12 0.9300 . ?
C13 C18 1.385(4) . ?
C13 C14 1.387(4) . ?
C14 C15 1.380(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.359(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.362(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.375(4) . ?
C19 C24 1.377(4) . ?
C20 C21 1.382(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.377(4) . ?
C22 C25 1.510(4) . ?
C23 C24 1.368(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 120.84(14) . . ?
O2 S1 N2 106.57(13) . . ?
O1 S1 N2 105.60(13) . . ?
O2 S1 C19 108.04(13) . . ?
O1 S1 C19 108.71(13) . . ?
N2 S1 C19 106.16(12) . . ?
C8 N1 C1 107.6(2) . . ?
C8 N1 C9 124.4(2) . . ?
C1 N1 C9 127.9(2) . . ?
C12 N2 C9 109.5(2) . . ?
C12 N2 S1 125.73(19) . . ?
C9 N2 S1 124.7(2) . . ?
N1 C1 C2 130.8(2) . . ?
N1 C1 C6 107.6(2) . . ?
C2 C1 C6 121.6(3) . . ?
C3 C2 C1 117.8(3) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 123.0(3) . . ?
C5 C4 Br1 119.4(2) . . ?
C3 C4 Br1 117.6(2) . . ?
C4 C5 C6 117.3(2) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 C7 133.4(3) . . ?
C1 C6 C7 107.0(2) . . ?
C8 C7 C6 107.1(2) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
C7 C8 N1 110.6(3) . . ?
C7 C8 H8 124.7 . . ?
N1 C8 H8 124.7 . . ?
N1 C9 N2 113.5(2) . . ?
N1 C9 C10 113.7(2) . . ?
N2 C9 C10 102.7(2) . . ?
N1 C9 H9 108.9 . . ?
N2 C9 H9 108.9 . . ?
C10 C9 H9 108.9 . . ?
C11 C10 C9 105.6(2) . . ?
C11 C10 H10A 110.6 . . ?
C9 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C12 C11 C13 128.9(3) . . ?
C12 C11 C10 108.8(3) . . ?
C13 C11 C10 122.3(3) . . ?
C11 C12 N2 112.8(3) . . ?
C11 C12 H12 123.6 . . ?
N2 C12 H12 123.6 . . ?
C18 C13 C14 117.4(3) . . ?
C18 C13 C11 122.0(3) . . ?
C14 C13 C11 120.6(3) . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 121.2(4) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 119.1(4) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 120.6(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 121.4(3) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
C20 C19 C24 120.6(3) . . ?
C20 C19 S1 119.5(2) . . ?
C24 C19 S1 119.8(2) . . ?
C19 C20 C21 119.0(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C22 C21 C20 121.5(3) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C23 C22 C21 117.8(3) . . ?
C23 C22 C25 120.8(3) . . ?
C21 C22 C25 121.3(3) . . ?
C24 C23 C22 121.9(3) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C23 C24 C19 119.2(3) . . ?
C23 C24 H24 120.4 . . ?
C19 C24 H24 120.4 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N2 C12 30.4(3) . . . . ?
O1 S1 N2 C12 160.1(2) . . . . ?
C19 S1 N2 C12 -84.6(2) . . . . ?
O2 S1 N2 C9 -152.6(2) . . . . ?
O1 S1 N2 C9 -22.9(3) . . . . ?
C19 S1 N2 C9 92.4(2) . . . . ?
C8 N1 C1 C2 -178.7(3) . . . . ?
C9 N1 C1 C2 4.3(5) . . . . ?
C8 N1 C1 C6 -0.1(3) . . . . ?
C9 N1 C1 C6 -177.1(2) . . . . ?
N1 C1 C2 C3 178.3(3) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C2 C3 C4 Br1 -178.8(2) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
Br1 C4 C5 C6 178.80(19) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C4 C5 C6 C7 -178.4(3) . . . . ?
N1 C1 C6 C5 -178.7(2) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
N1 C1 C6 C7 0.4(3) . . . . ?
C2 C1 C6 C7 179.2(3) . . . . ?
C5 C6 C7 C8 178.3(3) . . . . ?
C1 C6 C7 C8 -0.7(3) . . . . ?
C6 C7 C8 N1 0.6(3) . . . . ?
C1 N1 C8 C7 -0.4(3) . . . . ?
C9 N1 C8 C7 176.8(2) . . . . ?
C8 N1 C9 N2 119.1(3) . . . . ?
C1 N1 C9 N2 -64.3(4) . . . . ?
C8 N1 C9 C10 -124.0(3) . . . . ?
C1 N1 C9 C10 52.5(3) . . . . ?
C12 N2 C9 N1 116.2(3) . . . . ?
S1 N2 C9 N1 -61.2(3) . . . . ?
C12 N2 C9 C10 -7.0(3) . . . . ?
S1 N2 C9 C10 175.6(2) . . . . ?
N1 C9 C10 C11 -115.7(2) . . . . ?
N2 C9 C10 C11 7.3(3) . . . . ?
C9 C10 C11 C12 -5.3(3) . . . . ?
C9 C10 C11 C13 172.9(2) . . . . ?
C13 C11 C12 N2 -177.1(3) . . . . ?
C10 C11 C12 N2 1.0(3) . . . . ?
C9 N2 C12 C11 4.1(3) . . . . ?
S1 N2 C12 C11 -178.5(2) . . . . ?
C12 C11 C13 C18 -2.6(5) . . . . ?
C10 C11 C13 C18 179.6(3) . . . . ?
C12 C11 C13 C14 177.7(3) . . . . ?
C10 C11 C13 C14 -0.1(4) . . . . ?
C18 C13 C14 C15 0.9(5) . . . . ?
C11 C13 C14 C15 -179.4(3) . . . . ?
C13 C14 C15 C16 0.2(6) . . . . ?
C14 C15 C16 C17 -0.4(6) . . . . ?
C15 C16 C17 C18 -0.6(6) . . . . ?
C16 C17 C18 C13 1.8(5) . . . . ?
C14 C13 C18 C17 -2.0(5) . . . . ?
C11 C13 C18 C17 178.4(3) . . . . ?
O2 S1 C19 C20 -22.5(3) . . . . ?
O1 S1 C19 C20 -155.4(2) . . . . ?
N2 S1 C19 C20 91.5(2) . . . . ?
O2 S1 C19 C24 159.0(2) . . . . ?
O1 S1 C19 C24 26.2(3) . . . . ?
N2 S1 C19 C24 -87.0(2) . . . . ?
C24 C19 C20 C21 0.4(4) . . . . ?
S1 C19 C20 C21 -178.0(2) . . . . ?
C19 C20 C21 C22 0.5(5) . . . . ?
C20 C21 C22 C23 -0.6(5) . . . . ?
C20 C21 C22 C25 -177.7(3) . . . . ?
C21 C22 C23 C24 -0.1(5) . . . . ?
C25 C22 C23 C24 177.0(3) . . . . ?
C22 C23 C24 C19 0.9(5) . . . . ?
C20 C19 C24 C23 -1.1(4) . . . . ?
S1 C19 C24 C23 177.3(2) . . . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4

