# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_wv329
_database_code_depnum_ccdc_archive 'CCDC 1909120'
loop_
_audit_author_name
_audit_author_address
'Peter Mayer'
;LMU Muenchen
Germany
;

_audit_update_record             
;
2019-04-10 deposited with the CCDC.	2020-04-29 downloaded from the CCDC.
;

_chemical_name_common            AB124
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.030 #?# in millimeters
_exptl_crystal_size_mid          0.030 #?# in millimeters
_exptl_crystal_size_min          0.020 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      299.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.3910

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   12.8850(4)
_cell_length_b                   7.0118(2)
_cell_length_c                   18.0443(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.2010(10)
_cell_angle_gamma                90
_cell_volume                     1587.17(9)
_cell_measurement_temperature    299.(2) #?# in K
_cell_measurement_reflns_used    6776
_cell_measurement_theta_min      3.1202
_cell_measurement_theta_max      26.0968
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    9.051
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.84
_shelx_estimated_absorpt_T_min   0.773
_shelx_estimated_absorpt_T_max   0.840
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_diffrn_reflns_number            14753 #xl
_diffrn_reflns_av_R_equivalents  0.0286 #xl
_diffrn_reflns_av_unetI/netI     0.0259 #xl
_diffrn_reflns_limit_h_min       -16 #xl
_diffrn_reflns_limit_h_max       16 #xl
_diffrn_reflns_limit_k_min       -8 #xl
_diffrn_reflns_limit_k_max       8 #xl
_diffrn_reflns_limit_l_min       -22 #xl
_diffrn_reflns_limit_l_max       22 #xl
_diffrn_reflns_theta_min         3.120 #xl
_diffrn_reflns_theta_max         26.371 #xl
_diffrn_measured_fraction_theta_max 0.999 #xl
_diffrn_reflns_theta_full        25.242 #xl
_diffrn_measured_fraction_theta_full 0.999 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.999 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.999 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.999 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.999 #xl

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

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

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_reflns_number_total             3250 #xl
_reflns_number_gt                2693 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_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.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0155P)²+1.1418P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         3250 #xl
_refine_ls_number_parameters     174 #xl
_refine_ls_number_restraints     0 #xl
_refine_ls_R_factor_all          0.0330 #xl
_refine_ls_R_factor_gt           0.0229 #xl
_refine_ls_wR_factor_ref         0.0480 #xl
_refine_ls_wR_factor_gt          0.0450 #xl
_refine_ls_goodness_of_fit_ref   1.021 #xl
_refine_ls_restrained_S_all      1.021 #xl
_refine_ls_shift/su_max          0.001 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.317 #xl
_refine_diff_density_min         -0.420 #xl
_refine_diff_density_rms         0.066 #xl

_refine_special_details          
;
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'

_computing_publication_material  ?

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 0.91043(2) 0.24460(4) 0.47428(2) 0.04451(9) Uani 1 1 d . . . . .
Br2 Br 0.60432(2) 0.47372(4) 0.40937(2) 0.04440(9) Uani 1 1 d . . . . .
Br3 Br 0.75824(2) 0.28684(4) 0.24990(2) 0.04611(9) Uani 1 1 d . . . . .
Cu1 Cu 0.75998(3) 0.33550(5) 0.38058(2) 0.04495(11) Uani 1 1 d . . . . .
S1 S 0.34036(5) 0.35438(10) 0.31998(4) 0.03445(16) Uani 1 1 d . . . . .
N1 N 0.43124(16) 0.0145(3) 0.37363(12) 0.0336(5) Uani 1 1 d . . . . .
N2 N 0.30684(17) 0.0958(3) 0.43042(12) 0.0333(5) Uani 1 1 d . . . . .
N3 N 0.13807(17) 0.3462(3) 0.33838(13) 0.0353(5) Uani 1 1 d . . . . .
N4 N 0.14178(17) 0.3114(3) 0.22021(13) 0.0336(5) Uani 1 1 d . . . . .
C1 C 0.3589(2) 0.1483(4) 0.37681(14) 0.0298(6) Uani 1 1 d . . . . .
C2 C 0.4240(2) -0.1266(4) 0.42505(17) 0.0428(7) Uani 1 1 d . . . . .
H2 H 0.465322 -0.236539 0.434160 0.051 Uiso 1 1 calc R U . . .
C3 C 0.3469(2) -0.0772(4) 0.45944(16) 0.0432(7) Uani 1 1 d . . . . .
H3 H 0.324223 -0.147370 0.496534 0.052 Uiso 1 1 calc R U . . .
C4 C 0.4999(2) 0.0067(4) 0.31943(18) 0.0465(8) Uani 1 1 d . . . . .
H4A H 0.540683 -0.109137 0.326920 0.070 Uiso 1 1 calc R U . . .
H4B H 0.547312 0.114117 0.327311 0.070 Uiso 1 1 calc R U . . .
H4C H 0.456733 0.009874 0.268475 0.070 Uiso 1 1 calc R U . . .
C5 C 0.2208(2) 0.1901(4) 0.45900(17) 0.0455(8) Uani 1 1 d . . . . .
H5A H 0.247405 0.217048 0.512712 0.055 Uiso 1 1 calc R U . . .
H5B H 0.162271 0.100575 0.454638 0.055 Uiso 1 1 calc R U . . .
C6 C 0.1776(2) 0.3711(4) 0.42006(17) 0.0434(7) Uani 1 1 d . . . . .
H6A H 0.120175 0.417123 0.441895 0.052 Uiso 1 1 calc R U . . .
H6B H 0.233424 0.466933 0.429081 0.052 Uiso 1 1 calc R U . . .
C7 C 0.2023(2) 0.3335(4) 0.28973(15) 0.0294(6) Uani 1 1 d . . . . .
C8 C 0.0348(2) 0.3300(4) 0.2984(2) 0.0474(8) Uani 1 1 d . . . . .
H8 H -0.025702 0.331909 0.318374 0.057 Uiso 1 1 calc R U . . .
C9 C 0.0372(2) 0.3108(4) 0.2252(2) 0.0485(8) Uani 1 1 d . . . . .
H9 H -0.021724 0.299016 0.184698 0.058 Uiso 1 1 calc R U . . .
C10 C 0.1789(3) 0.2987(4) 0.14978(16) 0.0496(8) Uani 1 1 d . . . . .
H10A H 0.134288 0.212098 0.115423 0.074 Uiso 1 1 calc R U . . .
H10B H 0.251106 0.253217 0.160877 0.074 Uiso 1 1 calc R U . . .
H10C H 0.175874 0.422614 0.126712 0.074 Uiso 1 1 calc R U . . .


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 2.3507(5) . ?
Br2 Cu1 2.3891(5) . ?
Br3 Cu1 2.3777(5) . ?
S1 C7 1.744(3) . ?
S1 C1 1.757(3) . ?
N1 C1 1.332(3) . ?
N1 C2 1.374(3) . ?
N1 C4 1.462(3) . ?
N2 C1 1.348(3) . ?
N2 C3 1.375(4) . ?
N2 C5 1.481(3) . ?
N3 C7 1.340(3) . ?
N3 C8 1.366(4) . ?
N3 C6 1.456(4) . ?
N4 C7 1.326(3) . ?
N4 C9 1.371(4) . ?
N4 C10 1.460(3) . ?
C2 C3 1.331(4) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.495(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.335(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
Br1 Cu1 Br3 119.597(18) . . ?
Br1 Cu1 Br2 123.30(2) . . ?
Br3 Cu1 Br2 117.101(19) . . ?
C7 S1 C1 96.14(12) . . ?
C1 N1 C2 108.8(2) . . ?
C1 N1 C4 126.3(2) . . ?
C2 N1 C4 124.7(2) . . ?
C1 N2 C3 108.0(2) . . ?
C1 N2 C5 131.5(2) . . ?
C3 N2 C5 120.5(2) . . ?
C7 N3 C8 108.8(2) . . ?
C7 N3 C6 123.1(2) . . ?
C8 N3 C6 128.2(2) . . ?
C7 N4 C9 108.2(2) . . ?
C7 N4 C10 126.3(2) . . ?
C9 N4 C10 125.5(3) . . ?
N1 C1 N2 107.9(2) . . ?
N1 C1 S1 123.9(2) . . ?
N2 C1 S1 128.3(2) . . ?
C3 C2 N1 107.5(3) . . ?
C3 C2 H2 126.3 . . ?
N1 C2 H2 126.3 . . ?
C2 C3 N2 107.9(2) . . ?
C2 C3 H3 126.0 . . ?
N2 C3 H3 126.0 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 116.3(2) . . ?
N2 C5 H5A 108.2 . . ?
C6 C5 H5A 108.2 . . ?
N2 C5 H5B 108.2 . . ?
C6 C5 H5B 108.2 . . ?
H5A C5 H5B 107.4 . . ?
N3 C6 C5 112.4(2) . . ?
N3 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N3 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
N4 C7 N3 108.1(2) . . ?
N4 C7 S1 130.03(19) . . ?
N3 C7 S1 121.9(2) . . ?
C9 C8 N3 106.9(3) . . ?
C9 C8 H8 126.6 . . ?
N3 C8 H8 126.6 . . ?
C8 C9 N4 108.1(3) . . ?
C8 C9 H9 125.9 . . ?
N4 C9 H9 125.9 . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
C2 N1 C1 N2 1.0(3) . . . . ?
C4 N1 C1 N2 175.1(2) . . . . ?
C2 N1 C1 S1 -179.6(2) . . . . ?
C4 N1 C1 S1 -5.5(4) . . . . ?
C3 N2 C1 N1 -1.4(3) . . . . ?
C5 N2 C1 N1 178.8(3) . . . . ?
C3 N2 C1 S1 179.2(2) . . . . ?
C5 N2 C1 S1 -0.6(4) . . . . ?
C7 S1 C1 N1 131.0(2) . . . . ?
C7 S1 C1 N2 -49.8(3) . . . . ?
C1 N1 C2 C3 -0.1(3) . . . . ?
C4 N1 C2 C3 -174.3(3) . . . . ?
N1 C2 C3 N2 -0.8(3) . . . . ?
C1 N2 C3 C2 1.4(3) . . . . ?
C5 N2 C3 C2 -178.8(3) . . . . ?
C1 N2 C5 C6 3.8(5) . . . . ?
C3 N2 C5 C6 -176.0(3) . . . . ?
C7 N3 C6 C5 -76.9(3) . . . . ?
C8 N3 C6 C5 102.3(3) . . . . ?
N2 C5 C6 N3 56.5(4) . . . . ?
C9 N4 C7 N3 0.2(3) . . . . ?
C10 N4 C7 N3 177.6(2) . . . . ?
C9 N4 C7 S1 -177.3(2) . . . . ?
C10 N4 C7 S1 0.0(4) . . . . ?
C8 N3 C7 N4 0.5(3) . . . . ?
C6 N3 C7 N4 179.9(2) . . . . ?
C8 N3 C7 S1 178.3(2) . . . . ?
C6 N3 C7 S1 -2.3(4) . . . . ?
C1 S1 C7 N4 -118.2(3) . . . . ?
C1 S1 C7 N3 64.6(2) . . . . ?
C7 N3 C8 C9 -1.1(3) . . . . ?
C6 N3 C8 C9 179.6(3) . . . . ?
N3 C8 C9 N4 1.2(3) . . . . ?
C7 N4 C9 C8 -0.9(3) . . . . ?
C10 N4 C9 C8 -178.3(3) . . . . ?

_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.
;

_audit_block_code                Cu_Br_C10H14N4S_wv329_beheshti
_audit_creation_method           'APEX3 v2017.3-0'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H14 N4 S, Cu Br3'
_chemical_formula_sum            'C10 H14 Br3 Cu N4 S'
_chemical_formula_weight         525.58 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            4 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    2.200
_exptl_crystal_F_000             1008 #?# check!

####################################################################### 
# 
# 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_wv330
_database_code_depnum_ccdc_archive 'CCDC 1909121'
loop_
_audit_author_name
_audit_author_address
'Peter Mayer'
;LMU Muenchen
Germany
;
# end Validation Reply Form

_audit_update_record             
;
2019-04-10 deposited with the CCDC.	2020-04-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT232_wv330               
;
PROBLEM: Hirshfeld Test Diff (M-X)  Cu1      --S1_e     .       14.8 s.u.  
RESPONSE:  This Hirshfeld difference between Cu and a symmetry related S could
not be handled by a DELU instruction. The difference is no issue in the 
asymmetric unit. The atoms have been assigned correctly.
;

_chemical_name_common            AB124
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.070 #?# in millimeters
_exptl_crystal_size_mid          0.040 #?# in millimeters
_exptl_crystal_size_min          0.010 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      299.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.3910

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   9.5738(3)
_cell_length_b                   10.5680(3)
_cell_length_c                   7.7642(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.6780(10)
_cell_angle_gamma                90
_cell_volume                     759.91(4)
_cell_measurement_temperature    299.(2) #?# in K
_cell_measurement_reflns_used    4813
_cell_measurement_theta_min      2.9245
_cell_measurement_theta_max      27.1183
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    8.324
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.92
_shelx_estimated_absorpt_T_min   0.593
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_diffrn_reflns_number            7855 #xl
_diffrn_reflns_av_R_equivalents  0.0268 #xl
_diffrn_reflns_av_unetI/netI     0.0243 #xl
_diffrn_reflns_limit_h_min       -12 #xl
_diffrn_reflns_limit_h_max       12 #xl
_diffrn_reflns_limit_k_min       -13 #xl
_diffrn_reflns_limit_k_max       13 #xl
_diffrn_reflns_limit_l_min       -9 #xl
_diffrn_reflns_limit_l_max       9 #xl
_diffrn_reflns_theta_min         3.328 #xl
_diffrn_reflns_theta_max         27.100 #xl
_diffrn_measured_fraction_theta_max 0.996 #xl
_diffrn_reflns_theta_full        25.242 #xl
_diffrn_measured_fraction_theta_full 0.996 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.996 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.996 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.996 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.996 #xl

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

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

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_reflns_number_total             1669 #xl
_reflns_number_gt                1494 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_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.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+3.5406P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         1669 #xl
_refine_ls_number_parameters     92 #xl
_refine_ls_number_restraints     1 #xl
_refine_ls_R_factor_all          0.0426 #xl
_refine_ls_R_factor_gt           0.0376 #xl
_refine_ls_wR_factor_ref         0.0964 #xl
_refine_ls_wR_factor_gt          0.0929 #xl
_refine_ls_goodness_of_fit_ref   1.045 #xl
_refine_ls_restrained_S_all      1.050 #xl
_refine_ls_shift/su_max          0.000 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         1.779 #xl
_refine_diff_density_min         -1.365 #xl
_refine_diff_density_rms         0.129 #xl

_refine_special_details          
;
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'

_computing_publication_material  ?

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 0.68945(5) 0.41445(4) 1.05843(6) 0.03169(16) Uani 1 1 d . . . . .
Cu1 Cu 0.42199(7) 0.36685(6) 0.96179(8) 0.0390(2) Uani 1 1 d . U . . .
S1 S 0.35099(13) 0.26142(10) 0.68131(15) 0.0292(2) Uani 1 1 d . U . . .
N1 N 0.1176(4) 0.3618(4) 0.4425(5) 0.0266(8) Uani 1 1 d . . . . .
N2 N 0.3049(4) 0.4821(3) 0.4894(5) 0.0242(7) Uani 1 1 d . . . . .
C1 C 0.2562(4) 0.3715(4) 0.5368(5) 0.0219(8) Uani 1 1 d . . . . .
C2 C 0.0809(5) 0.4668(5) 0.3346(7) 0.0355(11) Uani 1 1 d . . . . .
H2 H -0.008305 0.482635 0.256173 0.043 Uiso 1 1 calc R U . . .
C3 C 0.1974(5) 0.5413(5) 0.3638(6) 0.0330(10) Uani 1 1 d . . . . .
H3 H 0.204391 0.618622 0.309375 0.040 Uiso 1 1 calc R U . . .
C4 C 0.0256(6) 0.2521(5) 0.4461(8) 0.0435(13) Uani 1 1 d . . . . .
H4A H -0.071688 0.271210 0.381753 0.065 Uiso 1 1 calc R U . . .
H4B H 0.027632 0.231810 0.567240 0.065 Uiso 1 1 calc R U . . .
H4C H 0.060280 0.181203 0.391681 0.065 Uiso 1 1 calc R U . . .
C5 C 0.4524(4) 0.5286(4) 0.5541(6) 0.0281(9) Uani 1 1 d . . . . .
H5A H 0.489336 0.506139 0.678478 0.034 Uiso 1 1 calc R U . . .
H5B H 0.453444 0.620080 0.544513 0.034 Uiso 1 1 calc R U . . .


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 2.5296(8) . ?
Br1 Cu1 2.5338(8) 3_667 ?
Cu1 S1 2.3866(13) . ?
Cu1 S1 2.4065(13) 4_566 ?
S1 C1 1.709(4) . ?
N1 C1 1.348(5) . ?
N1 C2 1.381(6) . ?
N1 C4 1.461(6) . ?
N2 C1 1.343(5) . ?
N2 C3 1.376(6) . ?
N2 C5 1.459(5) . ?
C2 C3 1.337(7) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C5 1.512(9) 3_666 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?

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 Br1 Cu1 77.55(3) . 3_667 ?
S1 Cu1 S1 108.48(3) . 4_566 ?
S1 Cu1 Br1 113.35(4) . . ?
S1 Cu1 Br1 110.38(4) 4_566 . ?
S1 Cu1 Br1 110.56(4) . 3_667 ?
S1 Cu1 Br1 111.57(4) 4_566 3_667 ?
Br1 Cu1 Br1 102.45(3) . 3_667 ?
C1 S1 Cu1 105.21(14) . . ?
C1 S1 Cu1 96.71(14) . 4_565 ?
Cu1 S1 Cu1 147.45(6) . 4_565 ?
C1 N1 C2 109.4(4) . . ?
C1 N1 C4 124.5(4) . . ?
C2 N1 C4 126.0(4) . . ?
C1 N2 C3 109.9(4) . . ?
C1 N2 C5 124.8(4) . . ?
C3 N2 C5 125.2(4) . . ?
N2 C1 N1 106.2(4) . . ?
N2 C1 S1 127.5(3) . . ?
N1 C1 S1 126.2(3) . . ?
C3 C2 N1 107.3(4) . . ?
C3 C2 H2 126.3 . . ?
N1 C2 H2 126.3 . . ?
C2 C3 N2 107.1(4) . . ?
C2 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C5 109.9(4) . 3_666 ?
N2 C5 H5A 109.7 . . ?
C5 C5 H5A 109.7 3_666 . ?
N2 C5 H5B 109.7 . . ?
C5 C5 H5B 109.7 3_666 . ?
H5A C5 H5B 108.2 . . ?

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
C3 N2 C1 N1 -0.7(5) . . . . ?
C5 N2 C1 N1 -177.3(4) . . . . ?
C3 N2 C1 S1 177.2(3) . . . . ?
C5 N2 C1 S1 0.6(6) . . . . ?
C2 N1 C1 N2 0.6(5) . . . . ?
C4 N1 C1 N2 176.5(4) . . . . ?
C2 N1 C1 S1 -177.3(3) . . . . ?
C4 N1 C1 S1 -1.4(6) . . . . ?
Cu1 S1 C1 N2 62.4(4) . . . . ?
Cu1 S1 C1 N2 -93.3(4) 4_565 . . . ?
Cu1 S1 C1 N1 -120.1(4) . . . . ?
Cu1 S1 C1 N1 84.2(4) 4_565 . . . ?
C1 N1 C2 C3 -0.3(5) . . . . ?
C4 N1 C2 C3 -176.1(5) . . . . ?
N1 C2 C3 N2 -0.1(6) . . . . ?
C1 N2 C3 C2 0.5(5) . . . . ?
C5 N2 C3 C2 177.1(4) . . . . ?
C1 N2 C5 C5 83.2(6) . . . 3_666 ?
C3 N2 C5 C5 -92.9(6) . . . 3_666 ?

_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.
;

_audit_block_code                Cu_Br_C10H14N4S2_wv330_beheshti
_audit_creation_method           'APEX3 v2017.3-0'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H14 Br2 Cu2 N4 S2'
_chemical_formula_sum            'C10 H14 Br2 Cu2 N4 S2'
_chemical_formula_weight         541.27 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            2 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    2.366
_exptl_crystal_F_000             524 #?# check!

