# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_BzTz
_database_code_depnum_ccdc_archive 'CCDC 1988747'
loop_
_audit_author_name
_audit_author_address
'A. Rossin' 'ICCOM CNR'
_audit_update_record             
;
2020-03-06 deposited with the CCDC.	2020-04-16 downloaded from the CCDC.
;

_audit_creation_date             2019-11-14T10:36:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_formula_moiety         'C15 H12 N O2 S, Br'
_chemical_formula_sum            'C15 H12 Br N O2 S'
_chemical_formula_weight         350.23

#----------------------------------------------------------------------------#
#                   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                   7.3944(5)
_cell_length_b                   14.8659(9)
_cell_length_c                   13.0018(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.5700(10)
_cell_angle_gamma                90
_cell_volume                     1428.68(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      4.5189
_cell_measurement_theta_max      74.5716
_cell_measurement_wavelength     1.54178

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704

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

_exptl_absorpt_coefficient_mu    5.294
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.049
_diffrn_reflns_number            2174
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         28.493
_diffrn_reflns_theta_max         74.563
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.585
_diffrn_measured_fraction_theta_max 0.568
_diffrn_reflns_Laue_measured_fraction_full 0.585
_diffrn_reflns_Laue_measured_fraction_max 0.568
_diffrn_reflns_point_group_measured_fraction_full 0.585
_diffrn_reflns_point_group_measured_fraction_max 0.568
_reflns_Friedel_coverage         0
_reflns_number_total             1666
_reflns_number_gt                1654
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_solution    'SIR 2014'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   mixed

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

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0934P)²+2.1985P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1666
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.053
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1537
_refine_ls_wR_factor_gt          0.1534
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_restrained_S_all      1.213
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.952
_refine_diff_density_rms         0.126

#----------------------------------------------------------------------------#
#                   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 0.2643(8) 0.1473(2) 1.0494(4) 0.0132(12) Uani 1 1 d . . . . .
C2 C 0.0955(8) 0.1478(3) 1.1096(3) 0.0147(13) Uani 1 1 d . . . . .
C3 C -0.0598(8) 0.1044(3) 1.0767(4) 0.0152(13) Uani 1 1 d . . . . .
H3 H -0.062061 0.073182 1.012944 0.018 Uiso 1 1 calc R U . . .
C4 C -0.2152(8) 0.1059(3) 1.1366(3) 0.0138(11) Uani 1 1 d . . . . .
H4 H -0.321643 0.074982 1.1142 0.017 Uiso 1 1 calc R U . . .
C5 C -0.2112(8) 0.1532(2) 1.2290(3) 0.0103(12) Uani 1 1 d . . . . .
C6 C -0.0547(8) 0.1988(3) 1.2614(3) 0.0128(12) Uani 1 1 d . . . . .
H6 H -0.054038 0.232549 1.323424 0.015 Uiso 1 1 calc R U . . .
C7 C 0.0988(8) 0.1950(3) 1.2039(3) 0.0120(11) Uani 1 1 d . . . . .
H7 H 0.206486 0.224128 1.227545 0.014 Uiso 1 1 calc R U . . .
C8 C -0.3809(8) 0.1594(3) 1.2910(3) 0.0118(11) Uani 1 1 d . . . . .
H8A H -0.433788 0.220267 1.283561 0.014 Uiso 1 1 calc R U . . .
H8B H -0.471024 0.115255 1.264561 0.014 Uiso 1 1 calc R U . . .
C9 C -0.3269(7) 0.2035(3) 1.4728(3) 0.0116(11) Uani 1 1 d . . . . .
H9 H -0.348922 0.265364 1.458885 0.014 Uiso 1 1 calc R U . . .
C10 C -0.2987(7) 0.0545(3) 1.4382(3) 0.0092(10) Uani 1 1 d . . . . .
C11 C -0.2567(7) 0.0561(3) 1.5435(3) 0.0124(11) Uani 1 1 d . . . . .
C12 C -0.2155(8) -0.0237(3) 1.5971(3) 0.0132(11) Uani 1 1 d . . . . .
H12 H -0.186745 -0.023526 1.668736 0.016 Uiso 1 1 calc R U . . .
C13 C -0.2190(8) -0.1025(3) 1.5406(4) 0.0148(12) Uani 1 1 d . . . . .
H13 H -0.191298 -0.15762 1.57445 0.018 Uiso 1 1 calc R U . . .
C14 C -0.2622(8) -0.1035(3) 1.4345(4) 0.0159(12) Uani 1 1 d . . . . .
H14 H -0.263145 -0.159197 1.39859 0.019 Uiso 1 1 calc R U . . .
C15 C -0.3038(8) -0.0246(3) 1.3811(4) 0.0131(11) Uani 1 1 d . . . . .
H15 H -0.333855 -0.024814 1.309593 0.016 Uiso 1 1 calc R U . . .
N1 N -0.3386(6) 0.1410(2) 1.4010(3) 0.0105(10) Uani 1 1 d . . . . .
O1 O 0.2453(7) 0.1060(3) 0.9593(3) 0.0238(11) Uani 1 1 d . . . . .
H100 H 0.365(19) 0.105(6) 0.933(8) 0.036 Uiso 1 1 d . U . . .
O2 O 0.4046(6) 0.1834(2) 1.0794(3) 0.0149(10) Uani 1 1 d . . . . .
S1 S -0.26972(18) 0.16488(6) 1.59137(8) 0.0140(4) Uani 1 1 d . . . . .
Br1 Br 0.61103(7) 0.08532(3) 0.83689(3) 0.0146(4) 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 O2 1.222(7) . ?
C1 O1 1.328(6) . ?
C1 C2 1.491(7) . ?
C2 C3 1.375(8) . ?
C2 C7 1.413(6) . ?
C3 C4 1.406(7) . ?
C3 H3 0.95 . ?
C4 C5 1.392(6) . ?
C4 H4 0.95 . ?
C5 C6 1.396(8) . ?
C5 C8 1.512(7) . ?
C6 C7 1.377(7) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 N1 1.481(6) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 N1 1.319(6) . ?
C9 S1 1.689(5) . ?
C9 H9 0.95 . ?
C10 C15 1.391(6) . ?
C10 C11 1.395(7) . ?
C10 N1 1.402(5) . ?
C11 C12 1.406(6) . ?
C11 S1 1.736(4) . ?
C12 C13 1.382(7) . ?
C12 H12 0.95 . ?
C13 C14 1.408(8) . ?
C13 H13 0.95 . ?
C14 C15 1.394(7) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
O1 H100 0.96(13) . ?

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 C1 O1 123.6(4) . . ?
O2 C1 C2 123.1(4) . . ?
O1 C1 C2 113.3(5) . . ?
C3 C2 C7 119.8(4) . . ?
C3 C2 C1 122.6(4) . . ?
C7 C2 C1 117.6(5) . . ?
C2 C3 C4 120.6(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.2(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 C8 119.5(5) . . ?
C6 C5 C8 120.2(4) . . ?
C7 C6 C5 120.4(4) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C2 119.8(5) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
N1 C8 C5 110.3(5) . . ?
N1 C8 H8A 109.6 . . ?
C5 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C5 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N1 C9 S1 114.6(3) . . ?
N1 C9 H9 122.7 . . ?
S1 C9 H9 122.7 . . ?
C15 C10 C11 122.7(4) . . ?
C15 C10 N1 126.0(4) . . ?
C11 C10 N1 111.2(4) . . ?
C10 C11 C12 120.7(4) . . ?
C10 C11 S1 110.8(3) . . ?
C12 C11 S1 128.5(4) . . ?
C13 C12 C11 116.8(4) . . ?
C13 C12 H12 121.6 . . ?
C11 C12 H12 121.6 . . ?
C12 C13 C14 122.0(4) . . ?
C12 C13 H13 119 . . ?
C14 C13 H13 119 . . ?
C15 C14 C13 121.3(4) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C10 C15 C14 116.3(4) . . ?
C10 C15 H15 121.8 . . ?
C14 C15 H15 121.8 . . ?
C9 N1 C10 113.1(4) . . ?
C9 N1 C8 124.2(4) . . ?
C10 N1 C8 122.7(4) . . ?
C1 O1 H100 104(6) . . ?
C9 S1 C11 90.2(2) . . ?

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 C1 C2 C3 -177.8(4) . . . . ?
O1 C1 C2 C3 3.9(6) . . . . ?
O2 C1 C2 C7 2.1(6) . . . . ?
O1 C1 C2 C7 -176.2(4) . . . . ?
C7 C2 C3 C4 -0.6(7) . . . . ?
C1 C2 C3 C4 179.3(4) . . . . ?
C2 C3 C4 C5 1.1(7) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C3 C4 C5 C8 176.6(4) . . . . ?
C4 C5 C6 C7 -2.1(6) . . . . ?
C8 C5 C6 C7 -178.4(4) . . . . ?
C5 C6 C7 C2 2.6(6) . . . . ?
C3 C2 C7 C6 -1.2(6) . . . . ?
C1 C2 C7 C6 178.9(4) . . . . ?
C4 C5 C8 N1 134.2(4) . . . . ?
C6 C5 C8 N1 -49.4(5) . . . . ?
C15 C10 C11 C12 0.5(8) . . . . ?
N1 C10 C11 C12 178.8(4) . . . . ?
C15 C10 C11 S1 -178.1(4) . . . . ?
N1 C10 C11 S1 0.3(5) . . . . ?
C10 C11 C12 C13 0.0(8) . . . . ?
S1 C11 C12 C13 178.3(4) . . . . ?
C11 C12 C13 C14 -0.3(8) . . . . ?
C12 C13 C14 C15 0.1(9) . . . . ?
C11 C10 C15 C14 -0.7(8) . . . . ?
N1 C10 C15 C14 -178.8(5) . . . . ?
C13 C14 C15 C10 0.4(8) . . . . ?
S1 C9 N1 C10 -0.6(6) . . . . ?
S1 C9 N1 C8 -178.0(4) . . . . ?
C15 C10 N1 C9 178.5(5) . . . . ?
C11 C10 N1 C9 0.2(6) . . . . ?
C15 C10 N1 C8 -4.1(8) . . . . ?
C11 C10 N1 C8 177.5(5) . . . . ?
C5 C8 N1 C9 103.9(5) . . . . ?
C5 C8 N1 C10 -73.2(5) . . . . ?
N1 C9 S1 C11 0.7(4) . . . . ?
C10 C11 S1 C9 -0.6(4) . . . . ?
C12 C11 S1 C9 -178.9(5) . . . . ?

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
_geom_hbond_publ_flag
C8 H8A Br1 0.99 2.99 3.843(4) 145.2 4_466 yes
C9 H9 Br1 0.95 2.74 3.625(4) 155.4 4_466 yes
C12 H12 Br1 0.95 3.13 3.770(4) 126 1_456 yes
C15 H15 Br1 0.95 2.9 3.696(6) 141.8 3_557 yes
O1 H100 Br1 0.96(13) 2.25(12) 3.190(4) 165(9) . yes

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
