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

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

data_s_peru_mj_513a_0m
_database_code_depnum_ccdc_archive 'CCDC 1545244'
_audit_update_record             
;
2017-04-21 deposited with the CCDC.
2017-07-03 downloaded from the CCDC.
;
_audit_creation_date             2017-04-20
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        2-anilino-3-cyanobenzo[b]thiophene
_chemical_formula_moiety         'C15 H10 N2 S'
_chemical_formula_sum            'C15 H10 N2 S'
_chemical_formula_weight         250.31
_chemical_melting_point          134-136
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   3.905(5)
_cell_length_b                   12.317(5)
_cell_length_c                   13.486(5)
_cell_angle_alpha                74.773(5)
_cell_angle_beta                 83.574(5)
_cell_angle_gamma                81.477(5)
_cell_volume                     617.2(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6962
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.069
_cell_measurement_theta_min      3.140
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6942
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.63
_diffrn_reflns_theta_min         1.57
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1376
_reflns_number_total             2311
_reflns_threshold_expression     >2σ(I)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT  A'
_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         0.222
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0619P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1369
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C15(H15), C6(H6), C3(H3), C11(H11), C14(H14), C5(H5), C4(H4),
 C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8815(7) 0.2222(3) 0.0371(2) 0.0490(8) Uani 1 1 d . . .
H1 H 0.8372 0.1939 -0.0171 0.059 Uiso 1 1 calc R . .
C2 C 0.8124(7) 0.3361(3) 0.0324(2) 0.0554(8) Uani 1 1 d . . .
H2 H 0.7201 0.3858 -0.0257 0.066 Uiso 1 1 calc R . .
C3 C 0.8790(8) 0.3773(3) 0.1132(2) 0.0569(9) Uani 1 1 d . . .
H3 H 0.8308 0.4546 0.1085 0.068 Uiso 1 1 calc R . .
C4 C 1.0145(7) 0.3067(3) 0.2004(2) 0.0523(8) Uani 1 1 d . . .
H4 H 1.0563 0.3357 0.2544 0.063 Uiso 1 1 calc R . .
C5 C 1.0878(7) 0.1920(3) 0.2068(2) 0.0407(7) Uani 1 1 d . . .
C6 C 1.0199(6) 0.1503(2) 0.1255(2) 0.0399(7) Uani 1 1 d . . .
C7 C 1.2304(7) 0.1015(3) 0.2889(2) 0.0420(7) Uani 1 1 d . . .
C8 C 1.3230(7) 0.1207(3) 0.3810(2) 0.0505(8) Uani 1 1 d . . .
C9 C 1.2613(7) -0.0033(3) 0.2698(2) 0.0403(7) Uani 1 1 d . . .
C10 C 1.3939(7) -0.2129(3) 0.3181(2) 0.0428(7) Uani 1 1 d . . .
C11 C 1.2755(8) -0.2993(3) 0.3964(2) 0.0559(9) Uani 1 1 d . . .
H11 H 1.1749 -0.2846 0.4581 0.067 Uiso 1 1 calc R . .
C12 C 1.3076(8) -0.4076(3) 0.3824(3) 0.0644(9) Uani 1 1 d . . .
H12 H 1.2297 -0.4660 0.4352 0.077 Uiso 1 1 calc R . .
C13 C 1.4528(8) -0.4299(3) 0.2917(3) 0.0620(9) Uani 1 1 d . . .
H13 H 1.4703 -0.5028 0.2825 0.074 Uiso 1 1 calc R . .
C14 C 1.5723(7) -0.3444(3) 0.2145(3) 0.0551(9) Uani 1 1 d . . .
H14 H 1.6723 -0.3595 0.1528 0.066 Uiso 1 1 calc R . .
C15 C 1.5453(7) -0.2361(3) 0.2275(2) 0.0475(8) Uani 1 1 d . . .
H15 H 1.6295 -0.1786 0.1750 0.057 Uiso 1 1 calc R . .
N1 N 1.4008(8) 0.1378(2) 0.4542(2) 0.0765(9) Uani 1 1 d . . .
N2 N 1.3700(6) -0.1036(2) 0.33509(19) 0.0509(7) Uani 1 1 d . . .
S1 S 1.12923(19) 0.00454(7) 0.14834(5) 0.0476(3) Uani 1 1 d . . .
H16 H 1.400(7) -0.103(2) 0.401(2) 0.070(10) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.375(4) . ?
C1 C6 1.394(4) . ?
C2 C3 1.381(4) . ?
C3 C4 1.372(4) . ?
C4 C5 1.380(4) . ?
C5 C6 1.393(4) . ?
C5 C7 1.443(4) . ?
C6 S1 1.736(3) . ?
C7 C8 1.418(4) . ?
C7 C9 1.366(4) . ?
C8 N1 1.144(3) . ?
C9 N2 1.357(4) . ?
C9 S1 1.746(3) . ?
C10 C11 1.381(4) . ?
C10 C15 1.376(4) . ?
C10 N2 1.411(4) . ?
C11 C12 1.382(4) . ?
C12 C13 1.366(4) . ?
C13 C14 1.368(4) . ?
C14 C15 1.378(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.1(3) . . ?
C1 C2 C3 120.6(3) . . ?
C4 C3 C2 121.5(3) . . ?
C3 C4 C5 119.1(3) . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 C7 129.6(3) . . ?
C6 C5 C7 110.9(3) . . ?
C1 C6 S1 126.2(2) . . ?
C5 C6 C1 121.3(3) . . ?
C5 C6 S1 112.5(2) . . ?
C8 C7 C5 122.5(3) . . ?
C9 C7 C5 113.7(2) . . ?
C9 C7 C8 123.7(3) . . ?
N1 C8 C7 178.7(3) . . ?
C7 C9 S1 111.6(2) . . ?
N2 C9 C7 126.4(3) . . ?
N2 C9 S1 122.0(2) . . ?
C11 C10 N2 118.7(3) . . ?
C15 C10 C11 119.5(3) . . ?
C15 C10 N2 121.7(3) . . ?
C10 C11 C12 119.6(3) . . ?
C13 C12 C11 120.7(3) . . ?
C12 C13 C14 119.7(3) . . ?
C13 C14 C15 120.3(3) . . ?
C10 C15 C14 120.2(3) . . ?
C9 N2 C10 127.3(2) . . ?
C6 S1 C9 91.33(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane & Dichloromethane'
####################################################################### 
# 
# 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_peru_sa-74
_database_code_depnum_ccdc_archive 'CCDC 1545245'
_audit_update_record             
;
2017-04-21 deposited with the CCDC.
2017-07-03 downloaded from the CCDC.
;
_audit_creation_date             2017-04-18
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
2-(isopropyl-amino)-3-(2-bromo-4,5-demethoxybenzoyl)-benzo[b]thiophene
_chemical_formula_moiety         'C20 H20 Br N O3 S'
_chemical_formula_sum            'C20 H20 Br N O3 S'
_chemical_formula_weight         434.34
_chemical_melting_point          130-132
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'
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'
N N 0.0061 0.0033 '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                   13.8970(6)
_cell_length_b                   9.2923(3)
_cell_length_c                   16.3213(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.260(3)
_cell_angle_gamma                90
_cell_volume                     1977.25(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5695
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.531
_cell_measurement_theta_min      2.564
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.203
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0633 before and 0.0440 after correction.
The Ratio of minimum to maximum transmission is 0.8600.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34415
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.788
_diffrn_reflns_theta_min         1.562
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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                3294
_reflns_number_total             5138
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²+0.9063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1048
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C14(H14), C8(H8), C7(H7), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C16(H16A,H16B,
 H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.051
;
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 0.87340(2) 0.40908(3) 0.54512(2) 0.06338(13) Uani 1 1 d . . . . .
S1 S 0.55357(5) 0.27741(7) 0.23265(4) 0.04580(17) Uani 1 1 d . . . . .
O3 O 0.96951(14) 0.9578(2) 0.58765(13) 0.0572(5) Uani 1 1 d . . . . .
O2 O 0.79219(14) 1.0427(2) 0.48676(13) 0.0553(5) Uani 1 1 d . . . . .
O1 O 0.59070(16) 0.5589(2) 0.46697(14) 0.0641(6) Uani 1 1 d . . . . .
N1 N 0.47730(16) 0.3753(2) 0.35148(15) 0.0478(6) Uani 1 1 d . . . . .
H1 H 0.4801 0.4326 0.3936 0.057 Uiso 1 1 calc R . . . .
C3 C 0.71194(18) 0.4468(3) 0.30619(15) 0.0359(5) Uani 1 1 d . . . . .
C10 C 0.74757(17) 0.6504(3) 0.46960(15) 0.0351(5) Uani 1 1 d . . . . .
C2 C 0.64370(17) 0.4660(3) 0.35608(15) 0.0354(5) Uani 1 1 d . . . . .
C12 C 0.80438(19) 0.8976(3) 0.49555(16) 0.0390(6) Uani 1 1 d . . . . .
C11 C 0.72977(18) 0.7986(3) 0.45633(15) 0.0381(5) Uani 1 1 d . . . . .
H11 H 0.6657 0.8303 0.4200 0.046 Uiso 1 1 calc R . . . .
C14 C 0.92106(18) 0.7064(3) 0.56368(16) 0.0420(6) Uani 1 1 d . . . . .
H14 H 0.9853 0.6744 0.5995 0.050 Uiso 1 1 calc R . . . .
C9 C 0.65639(19) 0.5534(3) 0.43128(16) 0.0397(6) Uani 1 1 d . . . . .
C13 C 0.90155(18) 0.8504(3) 0.55036(16) 0.0396(6) Uani 1 1 d . . . . .
C1 C 0.55412(19) 0.3816(2) 0.32205(15) 0.0369(5) Uani 1 1 d . . . . .
C8 C 0.80546(19) 0.5120(3) 0.31454(17) 0.0435(6) Uani 1 1 d . . . . .
H8 H 0.8341 0.5793 0.3584 0.052 Uiso 1 1 calc R . . . .
C4 C 0.67361(19) 0.3458(3) 0.23896(16) 0.0411(6) Uani 1 1 d . . . . .
C15 C 0.8432(2) 0.6079(3) 0.52273(17) 0.0410(6) Uani 1 1 d . . . . .
C19 C 0.38741(19) 0.2810(3) 0.32003(18) 0.0467(6) Uani 1 1 d . . . . .
H19 H 0.3841 0.2387 0.2641 0.056 Uiso 1 1 calc R . . . .
C7 C 0.8555(2) 0.4757(3) 0.25707(19) 0.0516(7) Uani 1 1 d . . . . .
H7 H 0.9175 0.5202 0.2628 0.062 Uiso 1 1 calc R . . . .
C5 C 0.7244(2) 0.3089(3) 0.18253(18) 0.0524(7) Uani 1 1 d . . . . .
H5 H 0.6974 0.2404 0.1391 0.063 Uiso 1 1 calc R . . . .
C6 C 0.8161(2) 0.3763(3) 0.19217(19) 0.0547(7) Uani 1 1 d . . . . .
H6 H 0.8512 0.3541 0.1545 0.066 Uiso 1 1 calc R . . . .
C18 C 0.3983(2) 0.1624(3) 0.3852(2) 0.0604(8) Uani 1 1 d . . . . .
H18A H 0.4555 0.1024 0.3875 0.091 Uiso 1 1 calc GR . . . .
H18B H 0.3368 0.1057 0.3680 0.091 Uiso 1 1 calc GR . . . .
H18C H 0.4097 0.2033 0.4418 0.091 Uiso 1 1 calc GR . . . .
C20 C 0.2914(2) 0.3693(4) 0.3064(2) 0.0724(10) Uani 1 1 d . . . . .
H20A H 0.2961 0.4162 0.3601 0.109 Uiso 1 1 calc GR . . . .
H20B H 0.2325 0.3073 0.2884 0.109 Uiso 1 1 calc GR . . . .
H20C H 0.2848 0.4404 0.2621 0.109 Uiso 1 1 calc GR . . . .
C17 C 1.0686(2) 0.9152(4) 0.6439(3) 0.0792(11) Uani 1 1 d . . . . .
H17A H 1.0991 0.8527 0.6129 0.119 Uiso 1 1 calc GR . . . .
H17B H 1.0628 0.8652 0.6935 0.119 Uiso 1 1 calc GR . . . .
H17C H 1.1109 0.9988 0.6634 0.119 Uiso 1 1 calc GR . . . .
C16 C 0.6921(3) 1.0946(3) 0.4416(3) 0.0834(12) Uani 1 1 d . . . . .
H16A H 0.6718 1.0680 0.3811 0.125 Uiso 1 1 calc GR . . . .
H16B H 0.6913 1.1976 0.4464 0.125 Uiso 1 1 calc GR . . . .
H16C H 0.6451 1.0536 0.4665 0.125 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 C15 1.902(3) . ?
S1 C1 1.749(2) . ?
S1 C4 1.755(3) . ?
O3 C13 1.364(3) . ?
O3 C17 1.422(4) . ?
O2 C12 1.360(3) . ?
O2 C16 1.415(4) . ?
O1 C9 1.242(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.315(3) . ?
N1 C19 1.466(3) . ?
C3 C2 1.459(3) . ?
C3 C8 1.397(3) . ?
C3 C4 1.401(3) . ?
C10 C11 1.402(3) . ?
C10 C9 1.504(3) . ?
C10 C15 1.370(3) . ?
C2 C9 1.431(3) . ?
C2 C1 1.412(3) . ?
C12 C11 1.368(3) . ?
C12 C13 1.407(3) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.368(4) . ?
C14 C15 1.398(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.389(4) . ?
C4 C5 1.384(4) . ?
C19 H19 0.9800 . ?
C19 C18 1.503(4) . ?
C19 C20 1.516(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.369(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(4) . ?
C6 H6 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C1 S1 C4 91.21(12) . . ?
C13 O3 C17 116.8(2) . . ?
C12 O2 C16 117.2(2) . . ?
C1 N1 H1 116.6 . . ?
C1 N1 C19 126.9(2) . . ?
C19 N1 H1 116.6 . . ?
C8 C3 C2 130.9(2) . . ?
C8 C3 C4 117.1(2) . . ?
C4 C3 C2 112.0(2) . . ?
C11 C10 C9 116.5(2) . . ?
C15 C10 C11 117.5(2) . . ?
C15 C10 C9 125.7(2) . . ?
C9 C2 C3 129.6(2) . . ?
C1 C2 C3 111.5(2) . . ?
C1 C2 C9 118.8(2) . . ?
O2 C12 C11 124.8(2) . . ?
O2 C12 C13 115.7(2) . . ?
C11 C12 C13 119.5(2) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.1(2) . . ?
C15 C14 H14 120.4 . . ?
O1 C9 C10 115.5(2) . . ?
O1 C9 C2 122.3(2) . . ?
C2 C9 C10 122.2(2) . . ?
O3 C13 C12 114.8(2) . . ?
O3 C13 C14 125.2(2) . . ?
C14 C13 C12 120.0(2) . . ?
N1 C1 S1 120.71(18) . . ?
N1 C1 C2 126.7(2) . . ?
C2 C1 S1 112.60(19) . . ?
C3 C8 H8 120.1 . . ?
C7 C8 C3 119.7(3) . . ?
C7 C8 H8 120.1 . . ?
C3 C4 S1 112.61(19) . . ?
C5 C4 S1 124.4(2) . . ?
C5 C4 C3 122.9(2) . . ?
C10 C15 Br1 120.21(19) . . ?
C10 C15 C14 122.3(2) . . ?
C14 C15 Br1 117.47(19) . . ?
N1 C19 H19 109.0 . . ?
N1 C19 C18 109.0(2) . . ?
N1 C19 C20 109.2(2) . . ?
C18 C19 H19 109.0 . . ?
C18 C19 C20 111.7(3) . . ?
C20 C19 H19 109.0 . . ?
C8 C7 H7 119.1 . . ?
C6 C7 C8 121.7(3) . . ?
C6 C7 H7 119.1 . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.4(3) . . ?
C6 C5 H5 120.8 . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane & dichloromethane'
