# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2023

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2191590'
loop_
_audit_author_name
_audit_author_address
'Melanie Rademeyer'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2022-07-20 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H5 Br2 Cu N O S'
_chemical_formula_sum            'C4 H5 Br2 Cu N O S'
_chemical_formula_weight         338.51

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'
Cu Cu 0.3201 1.2651 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   3.9875(2)
_cell_length_b                   15.7850(10)
_cell_length_c                   13.2012(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.532(2)
_cell_angle_gamma                90
_cell_volume                     825.53(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9864
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      26.42

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.724
_exptl_crystal_F_000             636
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.073
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_max          0.159
_exptl_absorpt_coefficient_mu    12.508
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1738
_exptl_absorpt_correction_T_max  0.2602
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker kappa, Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20574
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.581
_diffrn_reflns_theta_max         26.461
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1682
_reflns_number_gt                1555
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0256P)²+1.6437P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1682
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0593
_refine_ls_wR_factor_gt          0.0583
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_restrained_S_all      1.186
_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 0.99702(8) 0.58796(2) 0.28454(2) 0.01439(11) Uani 1 1 d . . . . .
Br2 Br 0.65800(7) 0.42869(2) 0.42720(2) 0.01198(10) Uani 1 1 d . . . . .
Cu1 Cu 0.65391(10) 0.58147(2) 0.42306(3) 0.01389(12) Uani 1 1 d . . . . .
S1 S 0.7116(2) 0.92889(5) 0.38044(7) 0.01771(19) Uani 1 1 d . . . . .
O1 O 0.7178(6) 0.69973(14) 0.45839(18) 0.0178(5) Uani 1 1 d . . . . .
N1 N 0.8066(7) 0.84113(17) 0.4515(2) 0.0150(6) Uani 1 1 d . . . . .
C2 C 0.4792(8) 0.7862(2) 0.3136(3) 0.0163(7) Uani 1 1 d . . . . .
C3 C 0.4796(8) 0.8690(2) 0.2899(3) 0.0168(7) Uani 1 1 d . . . . .
C4 C 1.0124(10) 0.8456(3) 0.5506(3) 0.0218(8) Uani 1 1 d . . . . .
C1 C 0.6705(8) 0.7687(2) 0.4104(2) 0.0135(7) Uani 1 1 d . . . . .
H3 H 0.363(9) 0.895(2) 0.233(3) 0.010(9) Uiso 1 1 d . . . . .
H2 H 0.353(11) 0.745(3) 0.274(3) 0.029(11) Uiso 1 1 d . . . . .
H4A H 1.083(11) 0.793(3) 0.569(3) 0.031(12) Uiso 1 1 d . . . . .
H4B H 0.895(12) 0.866(3) 0.599(4) 0.045(14) Uiso 1 1 d . . . . .
H4C H 1.175(12) 0.882(3) 0.547(3) 0.032(12) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.01529(18) 0.01459(17) 0.01374(18) 0.00134(12) 0.00362(13) -0.00189(12)
Br2 0.01345(18) 0.01038(17) 0.01240(17) 0.00012(11) 0.00270(12) -0.00035(11)
Cu1 0.0183(2) 0.0092(2) 0.0153(2) 0.00113(14) 0.00636(17) -0.00109(14)
S1 0.0220(4) 0.0105(4) 0.0204(4) 0.0020(3) 0.0009(3) -0.0011(3)
O1 0.0263(13) 0.0108(11) 0.0163(12) 0.0019(9) 0.0025(10) -0.0018(10)
N1 0.0190(14) 0.0100(13) 0.0160(14) 0.0017(11) 0.0014(11) -0.0007(11)
C2 0.0139(16) 0.0182(17) 0.0172(17) -0.0016(13) 0.0036(13) -0.0032(13)
C3 0.0137(16) 0.0210(18) 0.0153(17) 0.0032(14) 0.0002(13) 0.0004(13)
C4 0.026(2) 0.021(2) 0.0177(19) -0.0010(15) -0.0028(15) -0.0013(16)
C1 0.0143(16) 0.0121(16) 0.0154(17) 0.0001(12) 0.0078(13) -0.0012(12)

_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 Cu1 2.4073(5) . ?
Br2 Cu1 2.4124(5) . ?
Br2 Cu1 2.4575(5) 3_666 ?
Cu1 O1 1.934(2) . ?
S1 N1 1.692(3) . ?
S1 C3 1.711(4) . ?
O1 C1 1.264(4) . ?
N1 C1 1.352(4) . ?
N1 C4 1.465(4) . ?
C2 C3 1.344(5) . ?
C2 C1 1.438(5) . ?
C2 H2 0.94(4) . ?
C3 H3 0.93(4) . ?
C4 H4A 0.91(5) . ?
C4 H4B 0.89(5) . ?
C4 H4C 0.87(5) . ?

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
Cu1 Br2 Cu1 94.631(16) . 3_666 ?
O1 Cu1 Br1 94.10(7) . . ?
O1 Cu1 Br2 163.57(7) . . ?
Br1 Cu1 Br2 93.254(17) . . ?
O1 Cu1 Br2 86.21(7) . 3_666 ?
Br1 Cu1 Br2 175.65(2) . 3_666 ?
Br2 Cu1 Br2 85.370(16) . 3_666 ?
N1 S1 C3 90.21(15) . . ?
C1 O1 Cu1 134.7(2) . . ?
C1 N1 C4 123.9(3) . . ?
C1 N1 S1 114.5(2) . . ?
C4 N1 S1 121.6(2) . . ?
C3 C2 C1 112.2(3) . . ?
C3 C2 H2 124(3) . . ?
C1 C2 H2 124(3) . . ?
C2 C3 S1 113.0(3) . . ?
C2 C3 H3 127(2) . . ?
S1 C3 H3 120(2) . . ?
N1 C4 H4A 109(3) . . ?
N1 C4 H4B 111(3) . . ?
H4A C4 H4B 108(4) . . ?
N1 C4 H4C 109(3) . . ?
H4A C4 H4C 114(4) . . ?
H4B C4 H4C 105(4) . . ?
O1 C1 N1 119.8(3) . . ?
O1 C1 C2 130.1(3) . . ?
N1 C1 C2 110.1(3) . . ?

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
C3 S1 N1 C1 -0.2(3) . . . . ?
C3 S1 N1 C4 -178.6(3) . . . . ?
C1 C2 C3 S1 0.9(4) . . . . ?
N1 S1 C3 C2 -0.4(3) . . . . ?
Cu1 O1 C1 N1 -166.1(2) . . . . ?
Cu1 O1 C1 C2 15.2(5) . . . . ?
C4 N1 C1 O1 0.2(5) . . . . ?
S1 N1 C1 O1 -178.1(2) . . . . ?
C4 N1 C1 C2 179.1(3) . . . . ?
S1 N1 C1 C2 0.8(3) . . . . ?
C3 C2 C1 O1 177.7(3) . . . . ?
C3 C2 C1 N1 -1.0(4) . . . . ?

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
C3 H3 Br1 0.93(4) 3.11(4) 3.598(3) 114(3) 2_655 yes
C2 H2 Br1 0.94(4) 2.87(4) 3.669(3) 144(3) 1_455 yes
C3 H3 Br1 0.93(4) 3.11(4) 3.598(3) 114(3) 2_655 yes
C3 H3 Br2 0.93(4) 3.05(4) 3.483(3) 110(2) 2_655 yes
C2 H2 Br1 0.94(4) 2.87(4) 3.669(3) 144(3) 1_455 yes

_refine_diff_density_max         0.685
_refine_diff_density_min         -0.906
_refine_diff_density_rms         0.144

_shelx_res_file                  
;
TITL mo_SC64_0m_a.res in P2(1)/n
    shelx.res
    created by SHELXL-2018/3 at 07:43:31 on 10-Mar-2022
CELL  0.71073   3.9875  15.7850  13.2012   90.000   96.532   90.000
ZERR     4.00   0.0002   0.0010   0.0009    0.000    0.002    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    BR   CU   N    O    S
UNIT  16 20 8 4 4 4 4
MERG   2
EQIV $2 -x+3/2, y+1/2, -z+1/2
HTAB C3 Br1_$2
EQIV $3 x-1, y, z
HTAB C2 Br1_$3
HTAB C3 Br1_$2
HTAB C3 Br2_$2
HTAB C2 Br1_$3
FMAP   2
PLAN   20
ACTA
BOND   $H
CONF
LIST   6
L.S.  20
TEMP  -123.15
WGHT    0.025600    1.643700
FVAR       0.31634
BR1   3    0.997018    0.587961    0.284545    11.00000    0.01529    0.01459 =
         0.01374    0.00134    0.00362   -0.00189
BR2   3    0.658003    0.428688    0.427202    11.00000    0.01345    0.01038 =
         0.01240    0.00012    0.00270   -0.00035
CU1   4    0.653911    0.581473    0.423063    11.00000    0.01826    0.00918 =
         0.01527    0.00113    0.00636   -0.00109
S1    7    0.711616    0.928889    0.380441    11.00000    0.02198    0.01047 =
         0.02035    0.00200    0.00091   -0.00113
O1    6    0.717836    0.699732    0.458391    11.00000    0.02632    0.01084 =
         0.01628    0.00187    0.00251   -0.00182
N1    5    0.806556    0.841134    0.451504    11.00000    0.01896    0.01005 =
         0.01599    0.00170    0.00140   -0.00068
C2    1    0.479151    0.786171    0.313645    11.00000    0.01386    0.01816 =
         0.01721   -0.00158    0.00356   -0.00315
C3    1    0.479642    0.868957    0.289923    11.00000    0.01369    0.02095 =
         0.01529    0.00317    0.00016    0.00041
C4    1    1.012389    0.845579    0.550633    11.00000    0.02594    0.02066 =
         0.01767   -0.00100   -0.00280   -0.00132
C1    1    0.670480    0.768749    0.410393    11.00000    0.01425    0.01213 =
         0.01545    0.00009    0.00785   -0.00125
H3    2    0.363342    0.894979    0.232905    11.00000    0.00976
H2    2    0.353173    0.745144    0.274449    11.00000    0.02900
H4A   2    1.082639    0.792731    0.569298    11.00000    0.03105
H4B   2    0.894633    0.865827    0.598509    11.00000    0.04515
H4C   2    1.175177    0.881920    0.546518    11.00000    0.03176
HKLF    4




REM  mo_SC64_0m_a.res in P2(1)/n
REM wR2 = 0.0593, GooF = S = 1.186, Restrained GooF = 1.186 for all data
REM R1 = 0.0237 for 1555 Fo > 4sig(Fo) and 0.0264 for all 1682 data
REM 111 parameters refined using 0 restraints

END

WGHT      0.0256      1.6437

REM Highest difference peak  0.685,  deepest hole -0.906,  1-sigma level  0.144
Q1    1   0.9848  0.6451  0.2807  11.00000  0.05    0.68
Q2    1   0.6488  0.4937  0.4203  11.00000  0.05    0.58
Q3    1   0.8060  0.4593  0.4960  11.00000  0.05    0.53
Q4    1   1.1539  0.5750  0.3669  11.00000  0.05    0.52
Q5    1   0.5275  0.4614  0.3573  11.00000  0.05    0.52
Q6    1   0.8500  0.5899  0.2062  11.00000  0.05    0.49
Q7    1   0.8113  0.5389  0.4900  11.00000  0.05    0.48
Q8    1   0.4847  0.5547  0.3423  11.00000  0.05    0.45
Q9    1   0.8447  0.4164  0.5153  11.00000  0.05    0.42
Q10   1   0.8777  0.5178  0.2192  11.00000  0.05    0.42
Q11   1   0.5718  0.9098  0.3347  11.00000  0.05    0.41
Q12   1   0.7953  0.8776  0.4211  11.00000  0.05    0.40
Q13   1   0.7145  0.9813  0.3800  11.00000  0.05    0.36
Q14   1   1.0878  0.4189  0.4581  11.00000  0.05    0.36
Q15   1   0.5532  0.3562  0.3913  11.00000  0.05    0.35
Q16   1   0.7552  0.5994  0.4941  11.00000  0.05    0.35
Q17   1   0.7694  0.7046  0.5026  11.00000  0.05    0.33
Q18   1   0.4173  0.8242  0.3253  11.00000  0.05    0.32
Q19   1   1.3908  0.7022  0.6559  11.00000  0.05    0.32
Q20   1   0.1287  0.9054  0.1720  11.00000  0.05    0.31
;
_shelx_res_checksum              29267
