# 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_CS
_database_code_depnum_ccdc_archive 'CCDC 2005080'
loop_
_audit_author_name
_audit_author_address
'Adailton Bortoluzzi'
;Universidade Federal de Santa Catarina
Brazil
;
_audit_update_record             
;
2020-06-30 deposited with the CCDC.	2020-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 Cl2 Cu N S2'
_chemical_formula_sum            'C16 H19 Cl2 Cu N S2'
_chemical_formula_weight         423.88

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   11.1289(4)
_cell_length_b                   15.0127(6)
_cell_length_c                   10.5764(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1767.05(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5503
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      29.99

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             868
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.769
_shelx_estimated_absorpt_T_min   0.568
_shelx_estimated_absorpt_T_max   0.843
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6237
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   
;
Bruker APEX2, SAINT and SADABS, version 2011.8-0; Bruker AXS Inc., 
Madison, Wisconsin, USA
;
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10619
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.356
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2664
_reflns_number_gt                2299
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0224P)²+1.6583P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   diffmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2664
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0638
_refine_ls_wR_factor_gt          0.0587
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_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
Cu1 Cu 0.44235(2) 0.750000 0.72985(2) 0.01776(7) Uani 1 2 d S T P . .
Cl1 Cl 0.35908(6) 0.750000 0.53825(5) 0.03039(14) Uani 1 2 d S T P . .
Cl2 Cl 0.26084(5) 0.750000 0.85414(5) 0.02135(11) Uani 1 2 d S T P . .
N1 N 0.55785(17) 0.750000 0.87647(17) 0.0188(3) Uani 1 2 d S T P . .
H1 H 0.629236 0.750000 0.842407 0.023 Uiso 1 2 d R U P . .
C1 C 0.54787(15) 0.66745(10) 0.95169(15) 0.0222(3) Uani 1 1 d . . . . .
H1A H 0.464032 0.658815 0.980469 0.027 Uiso 1 1 calc R U . . .
H1B H 0.600581 0.670762 1.026946 0.027 Uiso 1 1 calc R U . . .
C2 C 0.58602(15) 0.59101(11) 0.86719(16) 0.0240(3) Uani 1 1 d . . . . .
H2A H 0.566997 0.533865 0.909389 0.029 Uiso 1 1 calc R U . . .
H2B H 0.674029 0.593570 0.854069 0.029 Uiso 1 1 calc R U . . .
S1 S 0.51018(4) 0.59516(3) 0.71374(4) 0.02055(9) Uani 1 1 d . . . . .
C3 C 0.39545(15) 0.51365(10) 0.73262(14) 0.0204(3) Uani 1 1 d . . . . .
C4 C 0.31780(15) 0.51197(11) 0.83586(15) 0.0233(3) Uani 1 1 d . . . . .
H4 H 0.321865 0.557239 0.898479 0.028 Uiso 1 1 calc R U . . .
C5 C 0.23424(16) 0.44349(11) 0.84654(17) 0.0276(3) Uani 1 1 d . . . . .
H5 H 0.183109 0.440900 0.918367 0.033 Uiso 1 1 calc R U . . .
C6 C 0.2250(2) 0.37915(13) 0.7535(2) 0.0365(4) Uani 1 1 d . . . . .
H6 H 0.166807 0.333123 0.760991 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3003(2) 0.38180(13) 0.64974(19) 0.0404(5) Uani 1 1 d . . . . .
H7 H 0.292759 0.338223 0.585090 0.048 Uiso 1 1 calc R U . . .
C8 C 0.38715(18) 0.44820(12) 0.63964(16) 0.0309(4) Uani 1 1 d . . . . .
H8 H 0.440570 0.448852 0.569590 0.037 Uiso 1 1 calc R U . . .


_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
Cu1 N1 2.0141(18) . y
Cu1 Cl1 2.2284(6) . y
Cu1 Cl2 2.4100(6) . y
Cu1 S1 2.4500(4) . y
Cu1 S1 2.4501(4) 7_575 ?
N1 C1 1.4769(18) . ?
N1 C1 1.4770(18) 7_575 ?
N1 H1 0.8722 . ?
C1 C2 1.515(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 S1 1.8303(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
S1 C3 1.7797(17) . ?
C3 C4 1.393(2) . ?
C3 C8 1.393(2) . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?

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 Cu1 Cl1 164.92(6) . . y
N1 Cu1 Cl2 96.60(6) . . y
Cl1 Cu1 Cl2 98.48(2) . . y
N1 Cu1 S1 81.774(19) . . y
Cl1 Cu1 S1 93.720(12) . . y
Cl2 Cu1 S1 107.228(11) . . y
N1 Cu1 S1 81.774(19) . 7_575 ?
Cl1 Cu1 S1 93.720(12) . 7_575 ?
Cl2 Cu1 S1 107.228(11) . 7_575 ?
S1 Cu1 S1 143.18(2) . 7_575 y
C1 N1 C1 114.10(17) . 7_575 ?
C1 N1 Cu1 111.51(10) . . ?
C1 N1 Cu1 111.51(10) 7_575 . ?
C1 N1 H1 106.9 . . ?
C1 N1 H1 106.9 7_575 . ?
Cu1 N1 H1 105.3 . . ?
N1 C1 C2 107.26(13) . . ?
N1 C1 H1A 110.3 . . ?
C2 C1 H1A 110.3 . . ?
N1 C1 H1B 110.3 . . ?
C2 C1 H1B 110.3 . . ?
H1A C1 H1B 108.5 . . ?
C1 C2 S1 111.60(11) . . ?
C1 C2 H2A 109.3 . . ?
S1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
S1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C3 S1 C2 102.00(7) . . ?
C3 S1 Cu1 115.06(5) . . ?
C2 S1 Cu1 96.47(5) . . ?
C4 C3 C8 119.96(16) . . ?
C4 C3 S1 123.06(12) . . ?
C8 C3 S1 116.95(13) . . ?
C5 C4 C3 119.46(16) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 120.58(17) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C7 C6 C5 119.99(18) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.17(18) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 119.78(17) . . ?
C7 C8 H8 120.1 . . ?
C3 C8 H8 120.1 . . ?

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
C1 N1 C1 C2 -168.16(12) 7_575 . . . ?
Cu1 N1 C1 C2 64.38(15) . . . . ?
N1 C1 C2 S1 -49.16(17) . . . . ?
C1 C2 S1 C3 -101.22(13) . . . . ?
C1 C2 S1 Cu1 16.16(12) . . . . ?
C2 S1 C3 C4 50.35(15) . . . . ?
Cu1 S1 C3 C4 -52.75(15) . . . . ?
C2 S1 C3 C8 -128.12(14) . . . . ?
Cu1 S1 C3 C8 128.79(12) . . . . ?
C8 C3 C4 C5 1.5(2) . . . . ?
S1 C3 C4 C5 -176.94(12) . . . . ?
C3 C4 C5 C6 -2.3(3) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C6 C7 C8 C3 -2.0(3) . . . . ?
C4 C3 C8 C7 0.7(3) . . . . ?
S1 C3 C8 C7 179.17(15) . . . . ?

_refine_diff_density_max         0.900
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_CSe
_database_code_depnum_ccdc_archive 'CCDC 2005081'
loop_
_audit_author_name
_audit_author_address
'Adailton Bortoluzzi'
;Universidade Federal de Santa Catarina
Brazil
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2020-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 Cl2 Cu N Se2'
_chemical_formula_sum            'C16 H19 Cl2 Cu N Se2'
_chemical_formula_weight         517.68

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'
Cl Cl 0.1484 0.1585 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   11.0926(6)
_cell_length_b                   15.3632(9)
_cell_length_c                   10.7113(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1825.40(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5647
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      30.05

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_F_000             1012
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    5.472
_shelx_estimated_absorpt_T_min   0.218
_shelx_estimated_absorpt_T_max   0.735
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4767
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   
;
Bruker APEX2, SAINT and SADABS, version 2011.8-0; Bruker AXS Inc., 
Madison, Wisconsin, USA
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15442
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.318
_diffrn_reflns_theta_max         30.079
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2770
_reflns_number_gt                2278
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0223P)²+2.2839P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   diffmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2770
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0613
_refine_ls_wR_factor_gt          0.0555
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_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
Cu1 Cu 0.43331(3) 0.750000 0.73182(3) 0.01867(9) Uani 1 2 d S T P . .
Cl1 Cl 0.34892(8) 0.750000 0.54171(7) 0.03042(18) Uani 1 2 d S T P . .
Cl2 Cl 0.25200(7) 0.750000 0.85538(7) 0.02370(16) Uani 1 2 d S T P . .
N1 N 0.5515(2) 0.750000 0.8773(2) 0.0200(5) Uani 1 2 d S T P . .
H1 H 0.622849 0.750000 0.843247 0.024 Uiso 1 2 d R U P . .
C1 C 0.5425(2) 0.66953(15) 0.9514(2) 0.0248(5) Uani 1 1 d . . . . .
H1A H 0.457926 0.659633 0.977127 0.030 Uiso 1 1 calc R U . . .
H1B H 0.592713 0.674414 1.027540 0.030 Uiso 1 1 calc R U . . .
C2 C 0.5862(2) 0.59435(15) 0.8716(2) 0.0281(5) Uani 1 1 d . . . . .
H2A H 0.566676 0.538671 0.913506 0.034 Uiso 1 1 calc R U . . .
H2B H 0.674863 0.597836 0.862312 0.034 Uiso 1 1 calc R U . . .
Se1 Se 0.51037(2) 0.59681(2) 0.70558(2) 0.02324(7) Uani 1 1 d . . . . .
C3 C 0.3882(2) 0.50958(14) 0.7312(2) 0.0238(4) Uani 1 1 d . . . . .
C4 C 0.3144(2) 0.50756(15) 0.8353(2) 0.0262(5) Uani 1 1 d . . . . .
H4 H 0.319849 0.552040 0.896628 0.031 Uiso 1 1 calc R U . . .
C5 C 0.2324(2) 0.44028(16) 0.8494(2) 0.0308(5) Uani 1 1 d . . . . .
H5 H 0.183293 0.437808 0.921963 0.037 Uiso 1 1 calc R U . . .
C6 C 0.2215(3) 0.37655(18) 0.7586(3) 0.0417(7) Uani 1 1 d . . . . .
H6 H 0.164570 0.330834 0.768436 0.050 Uiso 1 1 calc R U . . .
C7 C 0.2938(3) 0.37988(19) 0.6536(3) 0.0477(8) Uani 1 1 d . . . . .
H7 H 0.285416 0.337032 0.590259 0.057 Uiso 1 1 calc R U . . .
C8 C 0.3787(3) 0.44568(17) 0.6405(2) 0.0364(6) Uani 1 1 d . . . . .
H8 H 0.430042 0.446860 0.569577 0.044 Uiso 1 1 calc R U . . .


_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
Cu1 N1 2.036(3) . y
Cu1 Cl1 2.2411(9) . y
Cu1 Cl2 2.4076(8) . y
Cu1 Se1 2.5196(3) . y
Cu1 Se1 2.5196(3) 7_575 ?
N1 C1 1.472(3) 7_575 ?
N1 C1 1.473(3) . ?
N1 H1 0.8718 . ?
C1 C2 1.516(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 Se1 1.968(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
Se1 C3 1.925(2) . ?
C3 C4 1.384(3) . ?
C3 C8 1.385(3) . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?

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 Cu1 Cl1 164.62(8) . . y
N1 Cu1 Cl2 96.72(8) . . y
Cl1 Cu1 Cl2 98.66(3) . . y
N1 Cu1 Se1 82.36(3) . . y
Cl1 Cu1 Se1 92.312(13) . . y
Cl2 Cu1 Se1 110.164(10) . . y
N1 Cu1 Se1 82.36(3) . 7_575 ?
Cl1 Cu1 Se1 92.312(13) . 7_575 ?
Cl2 Cu1 Se1 110.164(10) . 7_575 ?
Se1 Cu1 Se1 138.154(19) . 7_575 y
C1 N1 C1 114.2(2) 7_575 . ?
C1 N1 Cu1 111.67(14) 7_575 . ?
C1 N1 Cu1 111.67(14) . . ?
C1 N1 H1 106.7 7_575 . ?
C1 N1 H1 106.7 . . ?
Cu1 N1 H1 105.3 . . ?
N1 C1 C2 108.31(19) . . ?
N1 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
N1 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
C1 C2 Se1 111.00(15) . . ?
C1 C2 H2A 109.4 . . ?
Se1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
Se1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C3 Se1 C2 99.13(10) . . ?
C3 Se1 Cu1 113.30(7) . . ?
C2 Se1 Cu1 93.56(7) . . ?
C4 C3 C8 120.2(2) . . ?
C4 C3 Se1 123.16(17) . . ?
C8 C3 Se1 116.59(19) . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C3 C8 C7 119.8(3) . . ?
C3 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?

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
C1 N1 C1 C2 -164.91(16) 7_575 . . . ?
Cu1 N1 C1 C2 67.2(2) . . . . ?
N1 C1 C2 Se1 -48.5(2) . . . . ?
C8 C3 C4 C5 1.3(4) . . . . ?
Se1 C3 C4 C5 -177.05(17) . . . . ?
C3 C4 C5 C6 -1.9(4) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C5 C6 C7 C8 1.4(5) . . . . ?
C4 C3 C8 C7 0.6(4) . . . . ?
Se1 C3 C8 C7 179.1(2) . . . . ?
C6 C7 C8 C3 -2.0(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
N1 H1 Cl1 0.87 2.79 3.412(3) 129 6_657 yes
N1 H1 Cl2 0.87 2.56 3.341(3) 149 6_657 yes

_refine_diff_density_max         0.853
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.095


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane (1:1 v:v)'
