# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1897274'
loop_
_audit_author_name
_audit_author_address
'Adrian Perez-Redondo'
;Universidad de Alcala
Spain
;
_audit_update_record             
;
2019-02-14 deposited with the CCDC.	2019-08-09 downloaded from the CCDC.
;

_audit_creation_date             2018-12-20T12:25:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C16 H9 N3 O2 S'
_chemical_formula_sum            'C16 H9 N3 O2 S'
_chemical_formula_weight         307.32
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.1680(4)
_cell_length_b                   15.6589(7)
_cell_length_c                   15.9344(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1289.49(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    71
_cell_measurement_theta_min      3
_cell_measurement_theta_max      21
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 1 0 0.193
0 1 0 0.081
0 -1 0 0.044
1 0 0 0.235
0 0 1 0.038
0 -1 -11 0.074


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  1.032
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      -0.034691
_diffrn_orient_matrix_ub_12      -0.024668
_diffrn_orient_matrix_ub_13      0.056782
_diffrn_orient_matrix_ub_21      -0.190135
_diffrn_orient_matrix_ub_22      0.007359
_diffrn_orient_matrix_ub_23      -0.009132
_diffrn_orient_matrix_ub_31      -0.0093
_diffrn_orient_matrix_ub_32      -0.058443
_diffrn_orient_matrix_ub_33      -0.025117
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_number            18859
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.649
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     1
_reflns_Friedel_coverage         0.703
_reflns_number_total             2968
_reflns_number_gt                2401
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+0.7103P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2968
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.0938
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 816 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.058

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8416(7) 0.4740(2) 0.4239(2) 0.0255(7) Uani 1 1 d . . . . .
C2 C 1.0419(7) 0.4293(2) 0.3863(2) 0.0298(8) Uani 1 1 d . . . . .
H2 H 1.1115 0.4463 0.3337 0.036 Uiso 1 1 calc R U . . .
C3 C 1.1362(8) 0.3585(2) 0.4291(2) 0.0332(8) Uani 1 1 d . . . . .
H3 H 1.2702 0.3254 0.4045 0.04 Uiso 1 1 calc R U . . .
C4 C 1.0383(8) 0.3350(2) 0.5073(2) 0.0364(9) Uani 1 1 d . . . . .
H4 H 1.1101 0.2871 0.5356 0.044 Uiso 1 1 calc R U . . .
C5 C 0.8393(8) 0.3799(2) 0.5445(2) 0.0312(8) Uani 1 1 d . . . . .
H5 H 0.7729 0.3632 0.5977 0.037 Uiso 1 1 calc R U . . .
C6 C 0.7378(7) 0.4504(2) 0.5023(2) 0.0280(9) Uani 1 1 d . . . . .
C7 C 0.5328(7) 0.5098(2) 0.5218(2) 0.0268(8) Uani 1 1 d . . . . .
C8 C 0.3563(7) 0.5219(2) 0.5863(2) 0.0292(8) Uani 1 1 d . . . . .
H8 H 0.3572 0.4863 0.6346 0.035 Uiso 1 1 calc R U . . .
C9 C 0.1784(8) 0.5877(2) 0.5781(2) 0.0314(8) Uani 1 1 d . . . . .
H9 H 0.0574 0.5954 0.6223 0.038 Uiso 1 1 calc R U . . .
C10 C 0.3346(7) 0.6302(2) 0.44928(19) 0.0248(7) Uani 1 1 d . . . . .
C11 C 0.5169(7) 0.5668(2) 0.45417(19) 0.0251(7) Uani 1 1 d . . . . .
C12 C 0.3258(8) 0.6847(2) 0.3745(2) 0.0264(7) Uani 1 1 d . . . . .
C13 C 0.1658(8) 0.7561(2) 0.3683(2) 0.0336(8) Uani 1 1 d . . . . .
H13 H 0.0575 0.7721 0.4139 0.04 Uiso 1 1 calc R U . . .
C14 C 0.1667(9) 0.8030(2) 0.2958(2) 0.0386(9) Uani 1 1 d . . . . .
H14 H 0.0573 0.8515 0.2903 0.046 Uiso 1 1 calc R U . . .
C15 C 0.3279(9) 0.7795(3) 0.2305(2) 0.0413(10) Uani 1 1 d . . . . .
H15 H 0.3291 0.8136 0.1812 0.05 Uiso 1 1 calc R U . . .
C16 C 0.4760(7) 0.6660(2) 0.3047(2) 0.0261(7) Uani 1 1 d . . . . .
N1 N 0.7109(6) 0.54806(17) 0.39525(17) 0.0252(7) Uani 1 1 d . . . . .
N2 N 0.1633(6) 0.64184(18) 0.51221(17) 0.0283(6) Uani 1 1 d . . . . .
N3 N 0.4826(7) 0.7108(2) 0.23336(18) 0.0361(8) Uani 1 1 d . . . . .
O1 O 0.5116(5) 0.50630(16) 0.25587(15) 0.0347(6) Uani 1 1 d . . . . .
O2 O 0.9115(5) 0.58827(17) 0.25793(16) 0.0366(7) Uani 1 1 d . . . . .
S1 S 0.66584(17) 0.57104(5) 0.29418(5) 0.0251(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.385(5) . ?
C1 C6 1.409(5) . ?
C1 N1 1.418(4) . ?
C2 C3 1.390(5) . ?
C2 H2 0.95 . ?
C3 C4 1.395(5) . ?
C3 H3 0.95 . ?
C4 C5 1.380(5) . ?
C4 H4 0.95 . ?
C5 C6 1.395(5) . ?
C5 H5 0.95 . ?
C6 C7 1.444(5) . ?
C7 C8 1.387(5) . ?
C7 C11 1.403(5) . ?
C8 C9 1.388(5) . ?
C8 H8 0.95 . ?
C9 N2 1.351(4) . ?
C9 H9 0.95 . ?
C10 N2 1.350(4) . ?
C10 C11 1.371(5) . ?
C10 C12 1.466(4) . ?
C11 N1 1.405(4) . ?
C12 C16 1.389(5) . ?
C12 C13 1.395(5) . ?
C13 C14 1.370(5) . ?
C13 H13 0.95 . ?
C14 C15 1.383(5) . ?
C14 H14 0.95 . ?
C15 N3 1.340(5) . ?
C15 H15 0.95 . ?
C16 N3 1.336(4) . ?
C16 S1 1.789(3) . ?
N1 S1 1.666(3) . ?
O1 S1 1.427(3) . ?
O2 S1 1.421(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.4(3) . . ?
C2 C1 N1 129.0(3) . . ?
C6 C1 N1 108.6(3) . . ?
C1 C2 C3 116.9(3) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C2 C3 C4 121.5(4) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C7 133.0(3) . . ?
C1 C6 C7 107.6(3) . . ?
C8 C7 C11 116.3(3) . . ?
C8 C7 C6 136.9(3) . . ?
C11 C7 C6 106.7(3) . . ?
C7 C8 C9 117.8(3) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
N2 C9 C8 125.3(3) . . ?
N2 C9 H9 117.3 . . ?
C8 C9 H9 117.3 . . ?
N2 C10 C11 120.4(3) . . ?
N2 C10 C12 120.3(3) . . ?
C11 C10 C12 119.3(3) . . ?
C10 C11 C7 123.1(3) . . ?
C10 C11 N1 127.1(3) . . ?
C7 C11 N1 109.8(3) . . ?
C16 C12 C13 116.4(3) . . ?
C16 C12 C10 120.7(3) . . ?
C13 C12 C10 122.9(3) . . ?
C14 C13 C12 119.2(3) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
N3 C15 C14 123.2(3) . . ?
N3 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
N3 C16 C12 125.8(3) . . ?
N3 C16 S1 110.1(3) . . ?
C12 C16 S1 123.9(3) . . ?
C11 N1 C1 107.2(3) . . ?
C11 N1 S1 120.1(2) . . ?
C1 N1 S1 123.7(2) . . ?
C10 N2 C9 117.0(3) . . ?
C16 N3 C15 115.8(3) . . ?
O2 S1 O1 117.41(16) . . ?
O2 S1 N1 108.01(16) . . ?
O1 S1 N1 109.76(15) . . ?
O2 S1 C16 111.73(16) . . ?
O1 S1 C16 108.89(16) . . ?
N1 S1 C16 99.55(15) . . ?


# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1897908'
loop_
_audit_author_name
_audit_author_address
'Adrian Perez-Redondo'
;Universidad de Alcala
Spain
;
_audit_update_record             
;
2019-02-18 deposited with the CCDC.	2019-08-09 downloaded from the CCDC.
;

_audit_creation_date             2018-12-21T10:55:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C16 H10 Br N3 O2 S'
_chemical_formula_sum            'C16 H10 Br N3 O2 S'
_chemical_formula_weight         388.24

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3252(6)
_cell_length_b                   9.8395(12)
_cell_length_c                   11.1869(13)
_cell_angle_alpha                65.080(9)
_cell_angle_beta                 71.705(9)
_cell_angle_gamma                67.231(6)
_cell_volume                     753.73(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    74
_cell_measurement_theta_min      3
_cell_measurement_theta_max      21
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -1 -8 0.373
-5 -6 -16 0.431
-13 -8 -14 0.425
-12 -4 -1 0.352
-15 -4 3 0.344
0 1 3 0.392
2 1 3 0.325
8 3 1 0.293
1 -3 0 0.296
-8 -12 -1 0.29
1 11 0 0.178


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  1.217
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      0.01
_diffrn_orient_matrix_ub_12      0
_diffrn_orient_matrix_ub_13      0
_diffrn_orient_matrix_ub_21      0
_diffrn_orient_matrix_ub_22      0.01
_diffrn_orient_matrix_ub_23      0
_diffrn_orient_matrix_ub_31      0
_diffrn_orient_matrix_ub_32      0
_diffrn_orient_matrix_ub_33      0.01
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.1071
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_number            24452
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.029
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             3451
_reflns_number_gt                2972
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²+0.8016P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3451
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.047
_refine_ls_R_factor_gt           0.036
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.082
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.088

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4459(3) 0.4061(3) 0.2063(2) 0.0228(5) Uani 1 1 d . . . . .
C2 C 0.7173(3) 0.4453(3) 0.1495(3) 0.0283(6) Uani 1 1 d . . . . .
H2 H 0.8349 0.4266 0.1005 0.034 Uiso 1 1 calc R U . . .
C3 C 0.6648(3) 0.5440(3) 0.2223(2) 0.0236(5) Uani 1 1 d . . . . .
H3 H 0.7456 0.5859 0.2293 0.028 Uiso 1 1 calc R U . . .
C4 C 0.4885(3) 0.5792(3) 0.2848(2) 0.0192(5) Uani 1 1 d . . . . .
C5 C 0.3883(3) 0.6667(3) 0.3756(2) 0.0192(5) Uani 1 1 d . . . . .
C6 C 0.4338(4) 0.7498(3) 0.4273(3) 0.0269(5) Uani 1 1 d . . . . .
H6 H 0.5496 0.7606 0.4021 0.032 Uiso 1 1 calc R U . . .
C7 C 0.3048(4) 0.8168(4) 0.5172(3) 0.0317(6) Uani 1 1 d . . . . .
H7 H 0.3314 0.877 0.5521 0.038 Uiso 1 1 calc R U . . .
C8 C 0.1371(4) 0.7968(3) 0.5566(3) 0.0301(6) Uani 1 1 d . . . . .
H8 H 0.0525 0.8412 0.6202 0.036 Uiso 1 1 calc R U . . .
C9 C 0.0900(3) 0.7139(3) 0.5058(3) 0.0257(5) Uani 1 1 d . . . . .
H9 H -0.0248 0.7007 0.533 0.031 Uiso 1 1 calc R U . . .
C10 C 0.2178(3) 0.6513(3) 0.4136(2) 0.0203(5) Uani 1 1 d . . . . .
C11 C 0.3748(3) 0.5160(3) 0.2701(2) 0.0183(5) Uani 1 1 d . . . . .
C12 C 0.1096(3) 0.8537(3) 0.1514(2) 0.0195(5) Uani 1 1 d . . . . .
C13 C 0.2363(3) 0.8599(3) 0.0354(3) 0.0237(5) Uani 1 1 d . . . . .
H13 H 0.2813 0.7773 -0.0002 0.028 Uiso 1 1 calc R U . . .
C14 C 0.2941(4) 0.9915(3) -0.0259(3) 0.0281(6) Uani 1 1 d . . . . .
H14 H 0.379 1.0029 -0.1066 0.034 Uiso 1 1 calc R U . . .
C15 C 0.2263(4) 1.1068(3) 0.0318(3) 0.0314(6) Uani 1 1 d . . . . .
H15 H 0.2708 1.1946 -0.01 0.038 Uiso 1 1 calc R U . . .
C16 C 0.0450(3) 0.9769(3) 0.2001(3) 0.0269(6) Uani 1 1 d . . . . .
H16 H -0.0443 0.9711 0.2783 0.032 Uiso 1 1 calc R U . . .
N1 N 0.6123(3) 0.3745(3) 0.1440(2) 0.0271(5) Uani 1 1 d . . . . .
N2 N 0.1985(3) 0.5674(3) 0.3417(2) 0.0193(4) Uani 1 1 d . . . . .
N3 N 0.1024(3) 1.1027(3) 0.1424(2) 0.0332(5) Uani 1 1 d . . . . .
O1 O 0.0595(2) 0.6073(2) 0.15409(19) 0.0278(4) Uani 1 1 d . . . . .
O2 O -0.1202(2) 0.7197(3) 0.3317(2) 0.0309(4) Uani 1 1 d . . . . .
S1 S 0.04287(7) 0.68346(8) 0.24285(6) 0.02062(14) Uani 1 1 d . . . . .
Br1 Br 0.31890(4) 0.27746(4) 0.21530(3) 0.03477(11) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.321(3) . ?
C1 C11 1.385(3) . ?
C1 Br1 1.895(3) . ?
C2 N1 1.340(4) . ?
C2 C3 1.383(4) . ?
C2 H2 0.95 . ?
C3 C4 1.389(3) . ?
C3 H3 0.95 . ?
C4 C11 1.396(3) . ?
C4 C5 1.456(3) . ?
C5 C6 1.386(4) . ?
C5 C10 1.397(3) . ?
C6 C7 1.390(4) . ?
C6 H6 0.95 . ?
C7 C8 1.391(4) . ?
C7 H7 0.95 . ?
C8 C9 1.386(4) . ?
C8 H8 0.95 . ?
C9 C10 1.384(3) . ?
C9 H9 0.95 . ?
C10 N2 1.448(3) . ?
C11 N2 1.442(3) . ?
C12 C16 1.387(4) . ?
C12 C13 1.387(3) . ?
C12 S1 1.755(3) . ?
C13 C14 1.381(4) . ?
C13 H13 0.95 . ?
C14 C15 1.384(4) . ?
C14 H14 0.95 . ?
C15 N3 1.336(4) . ?
C15 H15 0.95 . ?
C16 N3 1.330(4) . ?
C16 H16 0.95 . ?
N2 S1 1.702(2) . ?
O1 S1 1.4237(19) . ?
O2 S1 1.4267(18) . ?

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
N1 C1 C11 122.2(2) . . ?
N1 C1 Br1 115.00(19) . . ?
C11 C1 Br1 122.60(18) . . ?
N1 C2 C3 124.0(2) . . ?
N1 C2 H2 118 . . ?
C3 C2 H2 118 . . ?
C2 C3 C4 116.9(2) . . ?
C2 C3 H3 121.5 . . ?
C4 C3 H3 121.5 . . ?
C3 C4 C11 119.3(2) . . ?
C3 C4 C5 133.1(2) . . ?
C11 C4 C5 107.5(2) . . ?
C6 C5 C10 120.5(2) . . ?
C6 C5 C4 132.6(2) . . ?
C10 C5 C4 106.8(2) . . ?
C5 C6 C7 117.9(2) . . ?
C5 C6 H6 121 . . ?
C7 C6 H6 121 . . ?
C6 C7 C8 120.7(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 121.9(2) . . ?
C9 C8 H8 119 . . ?
C7 C8 H8 119 . . ?
C10 C9 C8 116.9(2) . . ?
C10 C9 H9 121.6 . . ?
C8 C9 H9 121.6 . . ?
C9 C10 C5 122.0(2) . . ?
C9 C10 N2 127.4(2) . . ?
C5 C10 N2 110.7(2) . . ?
C1 C11 C4 118.6(2) . . ?
C1 C11 N2 130.5(2) . . ?
C4 C11 N2 110.5(2) . . ?
C16 C12 C13 120.2(2) . . ?
C16 C12 S1 119.95(19) . . ?
C13 C12 S1 119.66(19) . . ?
C14 C13 C12 116.9(2) . . ?
C14 C13 H13 121.5 . . ?
C12 C13 H13 121.5 . . ?
C13 C14 C15 119.0(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N3 C15 C14 124.4(3) . . ?
N3 C15 H15 117.8 . . ?
C14 C15 H15 117.8 . . ?
N3 C16 C12 123.0(2) . . ?
N3 C16 H16 118.5 . . ?
C12 C16 H16 118.5 . . ?
C1 N1 C2 118.4(2) . . ?
C11 N2 C10 104.11(18) . . ?
C11 N2 S1 114.64(16) . . ?
C10 N2 S1 110.89(16) . . ?
C16 N3 C15 116.5(2) . . ?
O1 S1 O2 120.32(11) . . ?
O1 S1 N2 107.48(11) . . ?
O2 S1 N2 105.95(11) . . ?
O1 S1 C12 109.38(12) . . ?
O2 S1 C12 109.13(12) . . ?
N2 S1 C12 103.17(11) . . ?


# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
