# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_kbn22-150k
_database_code_depnum_ccdc_archive 'CCDC 2020826'
loop_
_audit_author_name
_audit_author_address
'Magali Allain'
;University of Angers, UMR CNRS
France
;
_audit_update_record             
;
2020-08-02 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;

_audit_creation_date             2019-04-10T16:07:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C14 H12 Br N3 O2 S'
_chemical_formula_sum            'C14 H12 Br N3 O2 S'
_chemical_formula_weight         366.24

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.3718(4)
_cell_length_b                   5.0528(2)
_cell_length_c                   19.9057(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.002(2)
_cell_angle_gamma                90
_cell_volume                     1444.63(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    3065
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      71.68

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

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.024
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_F_000             736

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

_exptl_absorpt_coefficient_mu    5.306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.60932
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 5.199
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_number            5496
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.077
_diffrn_reflns_theta_max         71.842
_diffrn_reflns_theta_full        70
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.968
_reflns_Friedel_coverage         0
_reflns_number_total             2750
_reflns_number_gt                2528
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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)+(0.0480P)²+1.0485P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2750
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_gt           0.035
_refine_ls_wR_factor_ref         0.0909
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.134
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.082

#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 '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 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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 0.66186(18) 0.6636(5) 0.47785(13) 0.0230(5) Uani 1 1 d . . . . .
H1 H 0.720754 0.662505 0.498745 0.028 Uiso 1 1 calc R U . . .
C2 C 0.63332(18) 0.4922(5) 0.42433(12) 0.0214(5) Uani 1 1 d . . . . .
C3 C 0.54064(18) 0.5648(5) 0.40952(13) 0.0222(5) Uani 1 1 d . . . . .
C4 C 0.48659(19) 0.4374(5) 0.35960(13) 0.0254(5) Uani 1 1 d . . . . .
C5 C 0.5255(2) 0.2321(6) 0.32523(13) 0.0285(6) Uani 1 1 d . . . . .
H5 H 0.490317 0.142255 0.292436 0.034 Uiso 1 1 calc R U . . .
C6 C 0.6190(2) 0.1566(5) 0.33954(13) 0.0262(5) Uani 1 1 d . . . . .
H6 H 0.64438 0.017495 0.31567 0.031 Uiso 1 1 calc R U . . .
C7 C 0.67345(18) 0.2839(5) 0.38789(12) 0.0218(5) Uani 1 1 d . . . . .
C8 C 0.85532(17) 0.3439(5) 0.28798(13) 0.0220(5) Uani 1 1 d . . . . .
C9 C 0.90625(19) 0.1371(6) 0.26151(14) 0.0265(5) Uani 1 1 d . . . . .
H9 H 0.936793 0.016485 0.289858 0.032 Uiso 1 1 calc R U . . .
C10 C 0.91095(19) 0.1127(6) 0.19233(14) 0.0299(6) Uani 1 1 d . . . . .
H10 H 0.945194 -0.025032 0.174492 0.036 Uiso 1 1 calc R U . . .
C11 C 0.86531(19) 0.2908(6) 0.14899(14) 0.0300(6) Uani 1 1 d . . . . .
C12 C 0.8131(2) 0.4909(6) 0.17688(15) 0.0336(6) Uani 1 1 d . . . . .
H12 H 0.781107 0.608773 0.148599 0.04 Uiso 1 1 calc R U . . .
C13 C 0.8073(2) 0.5196(6) 0.24588(15) 0.0297(6) Uani 1 1 d . . . . .
H13 H 0.771822 0.654701 0.263693 0.036 Uiso 1 1 calc R U . . .
C14 C 0.8746(3) 0.2682(8) 0.07388(16) 0.0487(9) Uani 1 1 d . . . . .
H14A H 0.815139 0.299343 0.05179 0.073 Uiso 1 1 calc R U . . .
H14B H 0.89597 0.093992 0.06297 0.073 Uiso 1 1 calc R U . . .
H14C H 0.918523 0.397058 0.059133 0.073 Uiso 1 1 calc R U . . .
N1 N 0.51975(15) 0.7634(4) 0.45238(10) 0.0226(4) Uani 1 1 d . . . . .
H1A H 0.466494 0.840737 0.453134 0.027 Uiso 1 1 calc R U . . .
N2 N 0.59372(15) 0.8244(5) 0.49396(11) 0.0253(5) Uani 1 1 d . . . . .
N3 N 0.76703(15) 0.2040(4) 0.40330(11) 0.0229(4) Uani 1 1 d . . . . .
H3 H 0.778103 0.06355 0.426642 0.027 Uiso 1 1 calc R U . . .
O1 O 0.83080(14) 0.6540(4) 0.38894(10) 0.0288(4) Uani 1 1 d . . . . .
O2 O 0.93610(13) 0.2681(4) 0.40503(9) 0.0286(4) Uani 1 1 d . . . . .
S1 S 0.85341(4) 0.38285(12) 0.37600(3) 0.02210(15) Uani 1 1 d . . . . .
BR1 Br 0.36367(2) 0.55752(7) 0.34231(2) 0.03369(12) 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 N2 1.321(3) . ?
C1 C2 1.422(4) . ?
C1 H1 0.93 . ?
C2 C3 1.403(4) . ?
C2 C7 1.413(3) . ?
C3 N1 1.357(3) . ?
C3 C4 1.397(4) . ?
C4 C5 1.372(4) . ?
C4 BR1 1.888(3) . ?
C5 C6 1.417(4) . ?
C5 H5 0.93 . ?
C6 C7 1.378(4) . ?
C6 H6 0.93 . ?
C7 N3 1.427(3) . ?
C8 C13 1.388(4) . ?
C8 C9 1.390(4) . ?
C8 S1 1.764(3) . ?
C9 C10 1.387(4) . ?
C9 H9 0.93 . ?
C10 C11 1.395(4) . ?
C10 H10 0.93 . ?
C11 C12 1.387(4) . ?
C11 C14 1.510(4) . ?
C12 C13 1.386(4) . ?
C12 H12 0.93 . ?
C13 H13 0.93 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
N1 N2 1.360(3) . ?
N1 H1A 0.86 . ?
N3 S1 1.643(2) . ?
N3 H3 0.86 . ?
O1 S1 1.4336(19) . ?
O2 S1 1.426(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C2 111.1(2) . . ?
N2 C1 H1 124.5 . . ?
C2 C1 H1 124.5 . . ?
C3 C2 C7 119.2(2) . . ?
C3 C2 C1 104.2(2) . . ?
C7 C2 C1 136.5(3) . . ?
N1 C3 C4 131.1(2) . . ?
N1 C3 C2 106.9(2) . . ?
C4 C3 C2 122.0(2) . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 BR1 123.2(2) . . ?
C3 C4 BR1 118.4(2) . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 121.7(2) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C2 118.3(2) . . ?
C6 C7 N3 121.7(2) . . ?
C2 C7 N3 119.9(2) . . ?
C13 C8 C9 120.6(2) . . ?
C13 C8 S1 120.2(2) . . ?
C9 C8 S1 119.1(2) . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 121.3(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 118.2(3) . . ?
C12 C11 C14 121.3(3) . . ?
C10 C11 C14 120.5(3) . . ?
C13 C12 C11 121.7(3) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C8 119.1(3) . . ?
C12 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 N1 N2 111.4(2) . . ?
C3 N1 H1A 124.3 . . ?
N2 N1 H1A 124.3 . . ?
C1 N2 N1 106.4(2) . . ?
C7 N3 S1 119.36(17) . . ?
C7 N3 H3 120.3 . . ?
S1 N3 H3 120.3 . . ?
O2 S1 O1 120.45(13) . . ?
O2 S1 N3 105.71(12) . . ?
O1 S1 N3 106.72(11) . . ?
O2 S1 C8 108.38(12) . . ?
O1 S1 C8 107.25(12) . . ?
N3 S1 C8 107.77(12) . . ?

