# 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 2018

####################################################################### 
# 
# 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_compound_1
_database_code_depnum_ccdc_archive 'CCDC 1844932'
_audit_update_record             
;
2018-05-23 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Co(NC5H4SeCH2C5H4N)Cl2
_chemical_formula_moiety         'C11 H10 Cl2 Co N2 Se'
_chemical_formula_sum            'C11 H10 Cl2 Co N2 Se'
_chemical_formula_iupac          ?
_chemical_formula_weight         379.00

_chemical_melting_point          '514.15-515.15 k'

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8194(3)
_cell_length_b                   8.2508(3)
_cell_length_c                   12.0455(5)
_cell_angle_alpha                94.298(2)
_cell_angle_beta                 107.224(2)
_cell_angle_gamma                115.874(2)
_cell_volume                     648.75(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.8247
_cell_measurement_theta_max      27.5110
_cell_measurement_temperature    293.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.940
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             370

_exptl_absorpt_coefficient_mu    4.516
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS (version 2016/2; Bruker, 2016) was used to perform the multi--scan
absorption correction.
;
_exptl_absorpt_correction_T_min  0.6837
_exptl_absorpt_correction_T_max  0.8622

_exptl_special_details           
;
;

_diffrn_ambient_temperature      293.(2)

_diffrn_source                   'microfocus X ray tube'
_diffrn_source_type              'Incoatex I\mS High Brilliance'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Incoatec Montel two dimensional X ray optics'

_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       '0.5 ° ω & φ scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            66615
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         30.62
_diffrn_reflns_theta_full        30.62
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             4002
_reflns_number_gt                3003
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0693
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.197
_refine_ls_number_reflns         4002
_refine_ls_number_parameters     167
_refine_ls_number_restraints     12
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0102P)²+0.8245P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.527
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Co Co 0.3494 0.9721 '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'

_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2016)'
_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  vim

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co Co1 0.28783(5) 0.48675(5) 0.77448(3) 0.02713(9) Uani d . . . 1.0 . .
Cl Cl1 0.59688(10) 0.51798(10) 0.86855(7) 0.04025(16) Uani d . . . 1.0 . .
Cl Cl2 0.00373(10) 0.24052(9) 0.77037(6) 0.03825(16) Uani d . . . 1.0 . .
N N1 0.2592(3) 0.4436(3) 0.59781(19) 0.0301(5) Uani d . . . 1.0 . .
N N2 0.2627(3) 0.7072(3) 0.83575(19) 0.0291(4) Uani d . . . 1.0 . .
C C1 0.2644(4) 0.5519(4) 0.5204(2) 0.0317(5) Uani d . . D 1.0 . .
C C2 0.2367(4) 0.4903(5) 0.4021(3) 0.0418(7) Uani d . . . 1.0 . .
H H2 0.242064 0.568061 0.349704 0.05 Uiso calc U . R 1.0 . .
C C3 0.2015(4) 0.3138(5) 0.3640(3) 0.0443(7) Uani d . . . 1.0 . .
H H3 0.179349 0.269618 0.284964 0.053 Uiso calc U . R 1.0 . .
C C4 0.1994(4) 0.2030(4) 0.4438(3) 0.0418(7) Uani d . . . 1.0 . .
H H4 0.177946 0.083625 0.420259 0.05 Uiso calc U . R 1.0 . .
C C5 0.2295(4) 0.2724(4) 0.5588(3) 0.0358(6) Uani d . . . 1.0 . .
H H5 0.229398 0.197646 0.612832 0.043 Uiso calc U . R 1.0 . .
C C6 0.3595(4) 0.8730(3) 0.8115(2) 0.0316(6) Uani d . . D 1.0 . .
C C7 0.3516(5) 1.0259(4) 0.8588(3) 0.0420(7) Uani d . . . 1.0 . .
H H7 0.41813 1.138985 0.840468 0.05 Uiso calc U . R 1.0 . .
C C8 0.2439(5) 1.0095(4) 0.9335(3) 0.0465(8) Uani d . . . 1.0 . .
H H8 0.238702 1.111846 0.966808 0.056 Uiso calc U . R 1.0 . .
C C9 0.1443(5) 0.8406(5) 0.9582(3) 0.0434(7) Uani d . . . 1.0 . .
H H9 0.07008 0.826565 1.007792 0.052 Uiso calc U . R 1.0 . .
C C10 0.1569(4) 0.6929(4) 0.9080(3) 0.0367(6) Uani d . . . 1.0 . .
H H10 0.089529 0.578487 0.924582 0.044 Uiso calc U . R 1.0 . .
Se Se1 0.31138(7) 0.79834(6) 0.56208(4) 0.04051(13) Uani d . P D 0.8020(13) A 1
C C11 0.486(2) 0.8808(18) 0.7339(10) 0.040(2) Uani d U P D 0.8020(13) A 1
H H11A 0.547559 0.801448 0.753272 0.048 Uiso calc U P R 0.8020(13) A 1
H H11B 0.595689 1.006624 0.750682 0.048 Uiso calc U P R 0.8020(13) A 1
C C11A 0.269(3) 0.735(2) 0.5657(19) 0.04051(13) Uani d . P D 0.1980(13) A 2
H H11C 0.143835 0.704134 0.58031 0.049 Uiso calc U P R 0.1980(13) A 2
H H11D 0.267727 0.800687 0.50206 0.049 Uiso calc U P R 0.1980(13) A 2
Se Se1A 0.4905(8) 0.8994(8) 0.7050(5) 0.0413(9) Uani d U P D 0.1980(13) A 2


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Co1 N2 . 2.022(2) ?
Co1 N1 . 2.059(2) ?
Co1 Cl1 . 2.2319(8) ?
Co1 Cl2 . 2.2462(7) ?
N1 C1 . 1.337(3) ?
N1 C5 . 1.349(3) ?
N2 C10 . 1.346(4) ?
N2 C6 . 1.348(3) ?
C1 C2 . 1.396(4) ?
C1 C11A . 1.552(16) ?
C1 Se1 . 1.899(3) ?
C2 C3 . 1.372(4) ?
C2 H2 . 0.93 ?
C3 C4 . 1.374(5) ?
C3 H3 . 0.93 ?
C4 C5 . 1.368(4) ?
C4 H4 . 0.93 ?
C5 H5 . 0.93 ?
C6 C7 . 1.379(4) ?
C6 C11 . 1.539(11) ?
C6 Se1A . 1.836(6) ?
C7 C8 . 1.380(5) ?
C7 H7 . 0.93 ?
C8 C9 . 1.374(5) ?
C8 H8 . 0.93 ?
C9 C10 . 1.375(4) ?
C9 H9 . 0.93 ?
C10 H10 . 0.93 ?
Se1 C11 . 1.979(12) ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
C11A Se1A . 1.88(2) ?
C11A H11C . 0.97 ?
C11A H11D . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 Co1 N1 . . 115.50(9) ?
N2 Co1 Cl1 . . 112.08(6) ?
N1 Co1 Cl1 . . 102.24(6) ?
N2 Co1 Cl2 . . 104.08(7) ?
N1 Co1 Cl2 . . 101.80(6) ?
Cl1 Co1 Cl2 . . 121.26(3) ?
C1 N1 C5 . . 117.9(2) ?
C1 N1 Co1 . . 131.73(18) ?
C5 N1 Co1 . . 110.37(18) ?
C10 N2 C6 . . 118.5(2) ?
C10 N2 Co1 . . 119.88(18) ?
C6 N2 Co1 . . 121.47(18) ?
N1 C1 C2 . . 121.5(3) ?
N1 C1 C11A . . 115.0(8) ?
C2 C1 C11A . . 122.8(8) ?
N1 C1 Se1 . . 123.2(2) ?
C2 C1 Se1 . . 115.3(2) ?
C3 C2 C1 . . 119.3(3) ?
C3 C2 H2 . . 120.4 ?
C1 C2 H2 . . 120.4 ?
C2 C3 C4 . . 119.3(3) ?
C2 C3 H3 . . 120.3 ?
C4 C3 H3 . . 120.3 ?
C5 C4 C3 . . 118.4(3) ?
C5 C4 H4 . . 120.8 ?
C3 C4 H4 . . 120.8 ?
N1 C5 C4 . . 123.5(3) ?
N1 C5 H5 . . 118.3 ?
C4 C5 H5 . . 118.3 ?
N2 C6 C7 . . 121.5(3) ?
N2 C6 C11 . . 115.4(5) ?
C7 C6 C11 . . 123.0(5) ?
N2 C6 Se1A . . 121.1(3) ?
C7 C6 Se1A . . 117.3(3) ?
C6 C7 C8 . . 119.3(3) ?
C6 C7 H7 . . 120.3 ?
C8 C7 H7 . . 120.3 ?
C9 C8 C7 . . 119.5(3) ?
C9 C8 H8 . . 120.3 ?
C7 C8 H8 . . 120.3 ?
C8 C9 C10 . . 118.6(3) ?
C8 C9 H9 . . 120.7 ?
C10 C9 H9 . . 120.7 ?
N2 C10 C9 . . 122.6(3) ?
N2 C10 H10 . . 118.7 ?
C9 C10 H10 . . 118.7 ?
C1 Se1 C11 . . 102.8(4) ?
C6 C11 Se1 . . 110.3(7) ?
C6 C11 H11A . . 109.6 ?
Se1 C11 H11A . . 109.6 ?
C6 C11 H11B . . 109.6 ?
Se1 C11 H11B . . 109.6 ?
H11A C11 H11B . . 108.1 ?
C1 C11A Se1A . . 116.8(11) ?
C1 C11A H11C . . 108.1 ?
Se1A C11A H11C . . 108.1 ?
C1 C11A H11D . . 108.1 ?
Se1A C11A H11D . . 108.1 ?
H11C C11A H11D . . 107.3 ?
C6 Se1A C11A . . 100.0(7) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . 1.0(4) ?
Co1 N1 C1 C2 . . . . -178.65(19) ?
C5 N1 C1 C11A . . . . 171.9(9) ?
Co1 N1 C1 C11A . . . . -7.8(9) ?
C5 N1 C1 Se1 . . . . -178.42(19) ?
Co1 N1 C1 Se1 . . . . 1.9(3) ?
N1 C1 C2 C3 . . . . 0.6(4) ?
C11A C1 C2 C3 . . . . -169.5(10) ?
Se1 C1 C2 C3 . . . . -179.9(2) ?
C1 C2 C3 C4 . . . . -1.6(4) ?
C2 C3 C4 C5 . . . . 1.0(4) ?
C1 N1 C5 C4 . . . . -1.7(4) ?
Co1 N1 C5 C4 . . . . 178.0(2) ?
C3 C4 C5 N1 . . . . 0.7(4) ?
C10 N2 C6 C7 . . . . -0.1(4) ?
Co1 N2 C6 C7 . . . . -176.35(19) ?
C10 N2 C6 C11 . . . . 176.9(6) ?
Co1 N2 C6 C11 . . . . 0.6(6) ?
C10 N2 C6 Se1A . . . . -175.3(3) ?
Co1 N2 C6 Se1A . . . . 8.4(3) ?
N2 C6 C7 C8 . . . . 0.6(4) ?
C11 C6 C7 C8 . . . . -176.1(6) ?
Se1A C6 C7 C8 . . . . 176.0(3) ?
C6 C7 C8 C9 . . . . -0.8(4) ?
C7 C8 C9 C10 . . . . 0.5(4) ?
C6 N2 C10 C9 . . . . -0.2(4) ?
Co1 N2 C10 C9 . . . . 176.1(2) ?
C8 C9 C10 N2 . . . . 0.0(4) ?
N1 C1 Se1 C11 . . . . 30.0(4) ?
C2 C1 Se1 C11 . . . . -149.5(4) ?
N2 C6 C11 Se1 . . . . 85.5(6) ?
C7 C6 C11 Se1 . . . . -97.5(7) ?
N1 C1 C11A Se1A . . . . 59.8(13) ?
C2 C1 C11A Se1A . . . . -129.4(9) ?
N2 C6 Se1A C11A . . . . 60.6(6) ?
C7 C6 Se1A C11A . . . . -114.8(6) ?
C1 C11A Se1A C6 . . . . -108.8(12) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 Cl2 2_556 0.93 2.88 3.696(3) 147.6 ?
C7 H7 Cl1 1_565 0.93 2.76 3.630(3) 157.0 ?
C9 H9 Cl2 2_567 0.93 2.94 3.791(3) 153.1 ?
C10 H10 Cl2 . 0.93 2.92 3.480(3) 120.0 ?
C11 H11A Cl1 . 0.97 2.92 3.807(12) 153.1 ?
C11 H11B Cl2 1_665 0.97 2.84 3.693(12) 147.1 ?



####################################################################### 
# 
# 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_compound_2d
_database_code_depnum_ccdc_archive 'CCDC 1844936'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2017.3-0'
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          '563.15-565.15 K'
_chemical_formula_moiety         'C12 H8 Cu N2 O4, 2(H2O)'
_chemical_formula_sum            'C12 H12 Cu N2 O6'
_chemical_formula_weight         343.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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'
N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3240 0.8257 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.114(2)
_cell_length_b                   7.550(3)
_cell_length_c                   9.106(3)
_cell_angle_alpha                75.934(15)
_cell_angle_beta                 85.21(2)
_cell_angle_gamma                72.06(2)
_cell_volume                     324.4(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      23.54
_cell_measurement_wavelength     0.56086

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_F_000             175
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    0.906
_shelx_estimated_absorpt_T_min   0.841
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6969
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_process_details   
;
        SADABS(Bruker, 2007) was used to perform the data scaling
        and semi-empirical absorption correction based on symmetry-
        related refkections.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.56086
_diffrn_radiation_type           AgK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30413
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.584
_diffrn_reflns_theta_max         23.699
_diffrn_reflns_theta_full        19.665
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1995
_reflns_number_gt                1899
_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       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2016)'
_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  vim
_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)+(0.0204P)²+0.2985P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1995
_refine_ls_number_parameters     119
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0578
_refine_ls_wR_factor_gt          0.0566
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.126
_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 0.500000 0.500000 0.500000 0.00935(7) Uani 1 2 d S . P . .
C1 C -0.0361(3) 0.67948(18) 0.56440(15) 0.0101(2) Uani 1 1 d . . . . .
N1 N 0.2812(2) 0.72938(16) 0.35976(12) 0.00951(19) Uani 1 1 d . . . . .
O1 O 0.16956(19) 0.54180(14) 0.62683(11) 0.01146(18) Uani 1 1 d . . . . .
O2 O -0.27508(19) 0.71578(14) 0.61623(11) 0.01385(19) Uani 1 1 d . . . . .
C2 C 0.0269(2) 0.80060(18) 0.41447(14) 0.0094(2) Uani 1 1 d . . . . .
C3 C -0.1564(3) 0.96977(19) 0.33994(15) 0.0123(2) Uani 1 1 d . . . . .
H3 H -0.335488 1.016245 0.379838 0.015 Uiso 1 1 calc R U . . .
C4 C -0.0702(3) 1.0701(2) 0.20434(16) 0.0150(2) Uani 1 1 d . . . . .
H4 H -0.188566 1.188613 0.151781 0.018 Uiso 1 1 calc R U . . .
C6 C 0.3621(3) 0.82209(19) 0.22652(15) 0.0127(2) Uani 1 1 d . . . . .
H6 H 0.538516 0.768726 0.186356 0.015 Uiso 1 1 calc R U . . .
C5 C 0.1912(3) 0.9947(2) 0.14694(16) 0.0151(3) Uani 1 1 d . . . . .
H5 H 0.251939 1.060612 0.054348 0.018 Uiso 1 1 calc R U . . .
O1W O -0.2692(4) 0.5593(4) 0.9415(2) 0.0285(8) Uani 0.927(16) 1 d . . P A 1
H1WA H -0.270(5) 0.592(4) 0.849(3) 0.037(7) Uiso 0.927(16) 1 d . . P A 1
H1WB H -0.387(11) 0.534(8) 0.978(7) 0.033(15) Uiso 0.464(8) 1 d . . P A 1
H1WC H -0.139(14) 0.529(10) 0.965(7) 0.040(17) Uiso 0.464(8) 1 d . . P A 1
O1WA O -0.227(19) 0.478(11) 0.922(5) 0.13(3) Uani 0.073(16) 1 d . U P A 2
H1WD H -0.270(5) 0.592(4) 0.849(3) 0.037(7) Uiso 0.073(16) 1 d . . P A 2
H1WE H -0.387(11) 0.534(8) 0.978(7) 0.033(15) Uiso 0.036(8) 1 d . . P A 2
H1WF H -0.139(14) 0.529(10) 0.965(7) 0.040(17) Uiso 0.036(8) 1 d . . P A 2


_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 O1 1.9522(12) 2_666 ?
Cu1 O1 1.9522(12) . ?
Cu1 N1 1.9624(13) 2_666 ?
Cu1 N1 1.9625(13) . ?
C1 O2 1.2457(16) . ?
C1 O1 1.2839(16) . ?
C1 C2 1.5182(19) . ?
N1 C6 1.3471(17) . ?
N1 C2 1.3489(17) . ?
C2 C3 1.3848(18) . ?
C3 C4 1.398(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(2) . ?
C4 H4 0.9500 . ?
C6 C5 1.3901(19) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
O1W H1WA 0.82(3) . ?
O1W H1WB 0.72(5) . ?
O1W H1WC 0.67(6) . ?
O1WA H1WD 0.93(6) . ?
O1WA H1WE 0.96(11) . ?
O1WA H1WF 0.85(7) . ?

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
O1 Cu1 O1 180.0 2_666 . ?
O1 Cu1 N1 83.82(5) 2_666 2_666 ?
O1 Cu1 N1 96.18(5) . 2_666 ?
O1 Cu1 N1 96.18(5) 2_666 . ?
O1 Cu1 N1 83.82(5) . . ?
N1 Cu1 N1 180.0 2_666 . ?
O2 C1 O1 125.10(12) . . ?
O2 C1 C2 119.75(12) . . ?
O1 C1 C2 115.14(11) . . ?
C6 N1 C2 119.78(12) . . ?
C6 N1 Cu1 127.78(9) . . ?
C2 N1 Cu1 112.33(9) . . ?
C1 O1 Cu1 114.32(9) . . ?
N1 C2 C3 122.42(12) . . ?
N1 C2 C1 113.79(11) . . ?
C3 C2 C1 123.79(12) . . ?
C2 C3 C4 118.07(12) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C5 C4 C3 119.36(13) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C6 C5 120.97(12) . . ?
N1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C5 C4 119.35(13) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
H1WA O1W H1WB 117(5) . . ?
H1WA O1W H1WC 109(6) . . ?
H1WB O1W H1WC 129(7) . . ?
H1WD O1WA H1WE 88(10) . . ?
H1WD O1WA H1WF 86(6) . . ?
H1WE O1WA H1WF 88(7) . . ?

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 O1 Cu1 170.46(10) . . . . ?
C2 C1 O1 Cu1 -8.26(14) . . . . ?
C6 N1 C2 C3 -1.29(19) . . . . ?
Cu1 N1 C2 C3 175.19(10) . . . . ?
C6 N1 C2 C1 179.26(11) . . . . ?
Cu1 N1 C2 C1 -4.26(13) . . . . ?
O2 C1 C2 N1 -170.34(11) . . . . ?
O1 C1 C2 N1 8.45(16) . . . . ?
O2 C1 C2 C3 10.2(2) . . . . ?
O1 C1 C2 C3 -170.99(12) . . . . ?
N1 C2 C3 C4 -1.0(2) . . . . ?
C1 C2 C3 C4 178.44(12) . . . . ?
C2 C3 C4 C5 1.9(2) . . . . ?
C2 N1 C6 C5 2.6(2) . . . . ?
Cu1 N1 C6 C5 -173.29(10) . . . . ?
N1 C6 C5 C4 -1.6(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?

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 O2 0.95 2.37 3.204(2) 146.7 2_476 yes
C6 H6 O1 0.95 2.64 3.125(2) 112.5 2_666 yes
O1W^a H1WA^a O2 0.82(3) 2.10(3) 2.909(2) 171(3) . yes
O1W^a H1WB^a O1W^a 0.72(5) 2.10(6) 2.815(4) 172(7) 2_467 yes
O1W^a H1WC^a O1W^a 0.67(6) 2.16(6) 2.833(4) 175(8) 2_567 yes
O1WA^b H1WD^b O2 0.93(6) 2.10(3) 2.91(4) 145(6) . yes
O1WA^b H1WE^b O1WA^b 0.96(11) 2.12(9) 2.98(18) 148(6) 2_467 yes
O1WA^b H1WF^b O1WA^b 0.85(7) 2.19(9) 2.96(13) 152(8) 2_567 yes

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.070



####################################################################### 
# 
# 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_compound_5
_database_code_depnum_ccdc_archive 'CCDC 1844939'
_audit_update_record             
;
2018-05-23 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Pd2(C11H9N2Se)2(O2CCH3)2(H2O)7
_chemical_formula_moiety         'C26 H24 N4 Pd2 O4 Se2, 7(H2 O)'
_chemical_formula_sum            'C26 H38 N4 O11 Pd2 Se2'
_chemical_formula_iupac          ?
_chemical_formula_weight         953.32

_chemical_melting_point          '501.15-503.15 K'

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

_cell_length_a                   21.3785(11)
_cell_length_b                   7.7887(4)
_cell_length_c                   20.5657(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.832(2)
_cell_angle_gamma                90
_cell_volume                     3363.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.3964
_cell_measurement_theta_max      30.5391
_cell_measurement_temperature    120.(2)

_exptl_crystal_description       'triangular plate'
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1880

_exptl_absorpt_coefficient_mu    3.294
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS (version 2016/2; Bruker, 2016) was used to perform the multi--scan
absorption correction.
;
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.80

_exptl_special_details           
;
;

_diffrn_ambient_temperature      120.(2)

_diffrn_source                   'microfocus X ray tube'
_diffrn_source_type              'Incoatex I\mS High Brilliance'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Incoatec Montel two dimensional X ray optics'

_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       '0.5 ° ω & φ scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            40389
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_full        30.57
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29

_refine_special_details          
;
;

_reflns_number_total             10285
_reflns_number_gt                8088
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0856
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.139
_refine_ls_number_reflns         10285
_refine_ls_number_parameters     462
_refine_ls_number_restraints     19
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0152P)²+12.4627P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.018
_refine_diff_density_min         -1.536
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'
Pd Pd -0.9988 1.0072 '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'

_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2016)'
_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  vim

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd Pd1 0.32957(2) 0.66381(3) 0.46403(2) 0.01065(4) Uani d . . . 1.0 . .
Pd Pd2 0.17276(2) 0.65995(3) 0.55180(2) 0.01284(4) Uani d . . . 1.0 . .
Se Se11 0.40299(2) 0.58847(4) 0.61478(2) 0.01714(6) Uani d . . . 1.0 . .
Se Se21 0.10018(2) 0.61751(5) 0.39852(2) 0.02258(7) Uani d . . . 1.0 . .
O O1 0.33065(10) 0.6404(3) 0.36192(9) 0.0162(4) Uani d . . . 1.0 . .
O O2 0.39169(10) 0.8704(3) 0.35867(10) 0.0209(5) Uani d . . . 1.0 . .
O O4 0.15680(10) 0.6551(3) 0.65001(10) 0.0212(5) Uani d . . . 1.0 . .
O O5 0.24895(11) 0.5215(3) 0.68194(10) 0.0258(5) Uani d . . . 1.0 . .
N N11 0.39463(11) 0.4707(3) 0.48599(11) 0.0126(5) Uani d . . . 1.0 . .
N N12 0.23798(11) 0.8504(3) 0.58109(11) 0.0138(5) Uani d . . . 1.0 . .
N N21 0.10710(11) 0.4732(3) 0.52355(12) 0.0174(5) Uani d . . . 1.0 . .
N N22 0.26762(11) 0.8661(3) 0.44402(11) 0.0127(5) Uani d . . . 1.0 . .
C C1 0.42511(14) 0.4463(4) 0.54915(13) 0.0146(6) Uani d . . . 1.0 . .
C C2 0.47269(14) 0.3239(4) 0.56555(15) 0.0187(6) Uani d . . . 1.0 . .
H H2 0.493196 0.308448 0.610316 0.022 Uiso calc U . R 1.0 . .
C C3 0.48974(15) 0.2254(4) 0.51624(15) 0.0202(7) Uani d . . . 1.0 . .
H H3 0.523172 0.143693 0.526278 0.024 Uiso calc U . R 1.0 . .
C C4 0.45756(14) 0.2467(4) 0.45174(15) 0.0193(6) Uani d . . . 1.0 . .
H H4 0.467832 0.177265 0.417246 0.023 Uiso calc U . R 1.0 . .
C C5 0.41070(14) 0.3690(4) 0.43805(14) 0.0164(6) Uani d . . . 1.0 . .
H H5 0.388827 0.382891 0.39368 0.02 Uiso calc U . R 1.0 . .
C C6 0.30161(13) 0.8288(4) 0.58385(12) 0.0127(5) Uani d . . . 1.0 . .
C C7 0.34374(14) 0.9660(4) 0.60384(13) 0.0156(6) Uani d . . . 1.0 . .
H H7 0.388153 0.951832 0.605505 0.019 Uiso calc U . R 1.0 . .
C C8 0.32025(15) 1.1208(4) 0.62098(14) 0.0190(6) Uani d . . . 1.0 . .
H H8 0.348317 1.214092 0.634436 0.023 Uiso calc U . R 1.0 . .
C C9 0.25516(15) 1.1395(4) 0.61844(15) 0.0221(7) Uani d . . . 1.0 . .
H H9 0.238073 1.2453 0.630045 0.027 Uiso calc U . R 1.0 . .
C C10 0.21638(15) 1.0026(4) 0.59892(14) 0.0199(6) Uani d . . . 1.0 . .
H H10 0.171991 1.015146 0.597835 0.024 Uiso calc U . R 1.0 . .
C C11 0.32205(13) 0.6614(4) 0.56082(12) 0.0120(5) Uani d . . . 1.0 . .
H H11 0.289109 0.574181 0.566341 0.014 Uiso calc U . R 1.0 . .
C C12 0.07655(14) 0.4619(4) 0.45967(14) 0.0176(6) Uani d . . . 1.0 . .
C C13 0.02947(15) 0.3399(4) 0.43912(16) 0.0242(7) Uani d . . . 1.0 . .
H H13 0.008046 0.335042 0.39429 0.029 Uiso calc U . R 1.0 . .
C C14 0.01458(16) 0.2260(4) 0.48526(18) 0.0276(8) Uani d . . . 1.0 . .
H H14 -0.01768 0.142193 0.472524 0.033 Uiso calc U . R 1.0 . .
C C15 0.04684(15) 0.2342(4) 0.55030(17) 0.0237(7) Uani d . . . 1.0 . .
H H15 0.037317 0.155786 0.582456 0.028 Uiso calc U . R 1.0 . .
C C16 0.09294(14) 0.3581(4) 0.56743(15) 0.0195(6) Uani d . . . 1.0 . .
H H16 0.115563 0.362561 0.611818 0.023 Uiso calc U . R 1.0 . .
C C17 0.20358(13) 0.8475(4) 0.43919(12) 0.0149(6) Uani d . . . 1.0 . .
C C18 0.16403(15) 0.9893(4) 0.42466(14) 0.0201(7) Uani d . . . 1.0 . .
H H18 0.119273 0.976029 0.420429 0.024 Uiso calc U . R 1.0 . .
C C19 0.18912(16) 1.1491(4) 0.41632(15) 0.0237(7) Uani d . . . 1.0 . .
H H19 0.161867 1.245332 0.405401 0.028 Uiso calc U . R 1.0 . .
C C20 0.25433(15) 1.1675(4) 0.42403(15) 0.0215(7) Uani d . . . 1.0 . .
H H20 0.272801 1.277069 0.420048 0.026 Uiso calc U . R 1.0 . .
C C21 0.29204(15) 1.0238(4) 0.43762(14) 0.0177(6) Uani d . . . 1.0 . .
H H21 0.336913 1.035998 0.442687 0.021 Uiso calc U . R 1.0 . .
C C22 0.18179(13) 0.6747(4) 0.45517(13) 0.0153(6) Uani d . . . 1.0 . .
H H22 0.214199 0.588542 0.447226 0.018 Uiso calc U . R 1.0 . .
C C23 0.36304(14) 0.7426(4) 0.33273(14) 0.0171(6) Uani d . . . 1.0 . .
C C24 0.36539(18) 0.6959(4) 0.26201(14) 0.0264(8) Uani d . . . 1.0 . .
H H24A 0.33553 0.601839 0.247621 0.04 Uiso calc U . R 1.0 . .
H H24B 0.408633 0.659447 0.258999 0.04 Uiso calc U . R 1.0 . .
H H24C 0.353538 0.795977 0.233493 0.04 Uiso calc U . R 1.0 . .
C C25 0.20183(15) 0.5960(4) 0.69505(14) 0.0200(6) Uani d . . . 1.0 . .
C C26 0.19294(18) 0.6208(5) 0.76510(15) 0.0328(9) Uani d . . . 1.0 . .
H H26A 0.198333 0.742436 0.77698 0.049 Uiso calc U . R 1.0 . .
H H26B 0.224622 0.552553 0.794897 0.049 Uiso calc U . R 1.0 . .
H H26C 0.150071 0.583469 0.769181 0.049 Uiso calc U . R 1.0 . .
O O1W 0.33216(11) 0.1523(3) 0.27564(11) 0.0249(5) Uani d . . D 1.0 . .
H H1WA 0.3525(14) 0.084(3) 0.3025(12) 0.037 Uiso d U . D 1.0 . .
H H1WB 0.3069(12) 0.094(4) 0.2484(12) 0.037 Uiso d U . D 1.0 . .
O O2W 0.50179(11) 0.0063(3) 0.32084(11) 0.0239(5) Uani d . . D 1.0 . .
H H2WA 0.5163(12) -0.051(4) 0.2931(11) 0.036 Uiso d U . D 1.0 . .
H H2WB 0.4710(9) -0.045(4) 0.3301(14) 0.036 Uiso d U . D 1.0 . .
O O3W 0.45009(12) 0.3158(3) 0.27045(14) 0.0371(7) Uani d . . D 1.0 . .
H H3WA 0.4693(13) 0.224(3) 0.282(2) 0.056 Uiso d U . D 1.0 . .
H H3WB 0.4118(8) 0.288(5) 0.258(2) 0.056 Uiso d U . D 1.0 . .
O O4W 0.24108(15) 0.4036(4) 0.29336(15) 0.0460(8) Uani d . . D 1.0 . .
H H4WA 0.2635(15) 0.487(3) 0.3098(19) 0.069 Uiso d U . D 1.0 . .
H H4WB 0.2664(13) 0.323(3) 0.288(2) 0.069 Uiso d U . D 1.0 . .
O O5W 0.12465(16) 0.3098(5) 0.22191(16) 0.0579(10) Uani d . . D 1.0 . .
H H5WA 0.1583(11) 0.333(6) 0.2513(15) 0.087 Uiso d U . D 1.0 . .
H H5WB 0.1032(12) 0.248(4) 0.2432(15) 0.087 Uiso d U . D 1.0 . .
O O6W 0.06733(14) 0.6002(4) 0.16575(17) 0.0397(8) Uani d . P D 0.8616(12) . .
H H6WA 0.0507(13) 0.638(5) 0.1979(11) 0.06 Uiso d U P D 0.8616(12) . .
H H6WB 0.0964(11) 0.674(3) 0.166(2) 0.06 Uiso d U P D 0.8616(12) . .
O O7W -0.0411(4) 0.566(2) 0.2157(5) 0.149(5) Uani d . P G 0.5418(12) . .
H H7WA -0.004106 0.581811 0.208593 0.223 Uiso d U P G 0.5418(12) . .
H H7WB -0.036411 0.513498 0.25199 0.223 Uiso d U P G 0.5418(12) . .
O O8W 0.0101(6) 0.240(3) 0.2632(5) 0.239(7) Uani d . P G 0.5966(12) . .
H H8WA -0.001512 0.142124 0.273396 0.358 Uiso d U P G 0.5966(12) . .
H H8WB -0.01667 0.308699 0.27343 0.358 Uiso d U P G 0.5966(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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Pd1 C11 . 2.027(2) ?
Pd1 N11 . 2.041(2) ?
Pd1 N22 . 2.050(2) ?
Pd1 O1 . 2.1122(19) ?
Pd2 N21 . 2.029(3) ?
Pd2 C22 . 2.036(3) ?
Pd2 N12 . 2.047(2) ?
Pd2 O4 . 2.111(2) ?
Se11 C1 . 1.874(3) ?
Se11 C11 . 1.956(3) ?
Se21 C12 . 1.883(3) ?
Se21 C22 . 1.959(3) ?
O1 C23 . 1.276(4) ?
O2 C23 . 1.237(4) ?
O4 C25 . 1.289(4) ?
O5 C25 . 1.236(4) ?
N11 C1 . 1.353(3) ?
N11 C5 . 1.358(4) ?
N12 C10 . 1.348(4) ?
N12 C6 . 1.361(4) ?
N21 C16 . 1.346(4) ?
N21 C12 . 1.355(4) ?
N22 C21 . 1.351(4) ?
N22 C17 . 1.362(4) ?
C1 C2 . 1.389(4) ?
C2 C3 . 1.375(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.385(4) ?
C3 H3 . 0.95 ?
C4 C5 . 1.373(4) ?
C4 H4 . 0.95 ?
C5 H5 . 0.95 ?
C6 C7 . 1.408(4) ?
C6 C11 . 1.481(4) ?
C7 C8 . 1.377(4) ?
C7 H7 . 0.95 ?
C8 C9 . 1.390(4) ?
C8 H8 . 0.95 ?
C9 C10 . 1.364(4) ?
C9 H9 . 0.95 ?
C10 H10 . 0.95 ?
C11 H11 . 1.0 ?
C12 C13 . 1.391(4) ?
C13 C14 . 1.379(5) ?
C13 H13 . 0.95 ?
C14 C15 . 1.386(5) ?
C14 H14 . 0.95 ?
C15 C16 . 1.377(4) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C17 C18 . 1.389(4) ?
C17 C22 . 1.481(4) ?
C18 C19 . 1.379(5) ?
C18 H18 . 0.95 ?
C19 C20 . 1.381(5) ?
C19 H19 . 0.95 ?
C20 C21 . 1.377(4) ?
C20 H20 . 0.95 ?
C21 H21 . 0.95 ?
C22 H22 . 1.0 ?
C23 C24 . 1.509(4) ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
C25 C26 . 1.501(4) ?
C26 H26A . 0.98 ?
C26 H26B . 0.98 ?
C26 H26C . 0.98 ?
O1W H1WA . 0.830(16) ?
O1W H1WB . 0.836(16) ?
O2W H2WA . 0.829(16) ?
O2W H2WB . 0.824(16) ?
O3W H3WA . 0.836(16) ?
O3W H3WB . 0.838(16) ?
O4W H4WA . 0.839(17) ?
O4W H4WB . 0.850(17) ?
O5W H5WA . 0.867(17) ?
O5W H5WB . 0.845(17) ?
O6W H6WA . 0.858(17) ?
O6W H6WB . 0.845(17) ?
O7W O8W 2 1.54(2) ?
O7W H7WA . 0.8399 ?
O7W H7WB . 0.8401 ?
O8W H8WA . 0.84 ?
O8W H8WB . 0.84 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 Pd1 N11 . . 87.27(10) ?
C11 Pd1 N22 . . 92.11(10) ?
N11 Pd1 N22 . . 177.19(9) ?
C11 Pd1 O1 . . 173.30(10) ?
N11 Pd1 O1 . . 91.27(8) ?
N22 Pd1 O1 . . 89.67(8) ?
N21 Pd2 C22 . . 87.04(11) ?
N21 Pd2 N12 . . 179.07(10) ?
C22 Pd2 N12 . . 93.55(10) ?
N21 Pd2 O4 . . 91.92(9) ?
C22 Pd2 O4 . . 175.62(10) ?
N12 Pd2 O4 . . 87.43(9) ?
C1 Se11 C11 . . 94.52(11) ?
C12 Se21 C22 . . 94.01(12) ?
C23 O1 Pd1 . . 121.47(18) ?
C25 O4 Pd2 . . 117.44(19) ?
C1 N11 C5 . . 118.3(2) ?
C1 N11 Pd1 . . 120.08(19) ?
C5 N11 Pd1 . . 121.60(18) ?
C10 N12 C6 . . 119.2(3) ?
C10 N12 Pd2 . . 117.9(2) ?
C6 N12 Pd2 . . 122.89(19) ?
C16 N21 C12 . . 118.6(3) ?
C16 N21 Pd2 . . 121.1(2) ?
C12 N21 Pd2 . . 120.3(2) ?
C21 N22 C17 . . 119.5(2) ?
C21 N22 Pd1 . . 118.13(19) ?
C17 N22 Pd1 . . 122.4(2) ?
N11 C1 C2 . . 121.9(3) ?
N11 C1 Se11 . . 117.9(2) ?
C2 C1 Se11 . . 120.2(2) ?
C3 C2 C1 . . 119.2(3) ?
C3 C2 H2 . . 120.4 ?
C1 C2 H2 . . 120.4 ?
C2 C3 C4 . . 119.1(3) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C5 C4 C3 . . 119.5(3) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
N11 C5 C4 . . 122.0(3) ?
N11 C5 H5 . . 119.0 ?
C4 C5 H5 . . 119.0 ?
N12 C6 C7 . . 119.9(3) ?
N12 C6 C11 . . 116.6(2) ?
C7 C6 C11 . . 123.4(3) ?
C8 C7 C6 . . 119.7(3) ?
C8 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C7 C8 C9 . . 119.5(3) ?
C7 C8 H8 . . 120.2 ?
C9 C8 H8 . . 120.2 ?
C10 C9 C8 . . 118.5(3) ?
C10 C9 H9 . . 120.7 ?
C8 C9 H9 . . 120.7 ?
N12 C10 C9 . . 123.2(3) ?
N12 C10 H10 . . 118.4 ?
C9 C10 H10 . . 118.4 ?
C6 C11 Se11 . . 110.90(17) ?
C6 C11 Pd1 . . 112.85(18) ?
Se11 C11 Pd1 . . 109.56(13) ?
C6 C11 H11 . . 107.8 ?
Se11 C11 H11 . . 107.8 ?
Pd1 C11 H11 . . 107.8 ?
N21 C12 C13 . . 121.9(3) ?
N21 C12 Se21 . . 117.7(2) ?
C13 C12 Se21 . . 120.4(2) ?
C14 C13 C12 . . 118.5(3) ?
C14 C13 H13 . . 120.7 ?
C12 C13 H13 . . 120.7 ?
C13 C14 C15 . . 119.8(3) ?
C13 C14 H14 . . 120.1 ?
C15 C14 H14 . . 120.1 ?
C16 C15 C14 . . 118.8(3) ?
C16 C15 H15 . . 120.6 ?
C14 C15 H15 . . 120.6 ?
N21 C16 C15 . . 122.4(3) ?
N21 C16 H16 . . 118.8 ?
C15 C16 H16 . . 118.8 ?
N22 C17 C18 . . 119.6(3) ?
N22 C17 C22 . . 115.8(2) ?
C18 C17 C22 . . 124.5(3) ?
C19 C18 C17 . . 120.6(3) ?
C19 C18 H18 . . 119.7 ?
C17 C18 H18 . . 119.7 ?
C18 C19 C20 . . 119.2(3) ?
C18 C19 H19 . . 120.4 ?
C20 C19 H19 . . 120.4 ?
C21 C20 C19 . . 118.6(3) ?
C21 C20 H20 . . 120.7 ?
C19 C20 H20 . . 120.7 ?
N22 C21 C20 . . 122.5(3) ?
N22 C21 H21 . . 118.8 ?
C20 C21 H21 . . 118.8 ?
C17 C22 Se21 . . 110.92(19) ?
C17 C22 Pd2 . . 111.07(19) ?
Se21 C22 Pd2 . . 109.30(13) ?
C17 C22 H22 . . 108.5 ?
Se21 C22 H22 . . 108.5 ?
Pd2 C22 H22 . . 108.5 ?
O2 C23 O1 . . 124.6(3) ?
O2 C23 C24 . . 120.4(3) ?
O1 C23 C24 . . 115.0(3) ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
O5 C25 O4 . . 122.7(3) ?
O5 C25 C26 . . 121.7(3) ?
O4 C25 C26 . . 115.6(3) ?
C25 C26 H26A . . 109.5 ?
C25 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C25 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
H1WA O1W H1WB . . 107.(3) ?
H2WA O2W H2WB . . 108.(3) ?
H3WA O3W H3WB . . 105.(3) ?
H4WA O4W H4WB . . 107.(3) ?
H5WA O5W H5WB . . 103.(3) ?
H6WA O6W H6WB . . 100.(3) ?
O8W O7W H7WA 2 . 63.1 ?
O8W O7W H7WB 2 . 101.7 ?
H7WA O7W H7WB . . 105.5 ?
O7W O8W H8WA 2_545 . 42.3 ?
O7W O8W H8WB 2_545 . 140.4 ?
H8WA O8W H8WB . . 105.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N11 C1 C2 . . . . 1.4(4) ?
Pd1 N11 C1 C2 . . . . -175.7(2) ?
C5 N11 C1 Se11 . . . . 179.6(2) ?
Pd1 N11 C1 Se11 . . . . 2.5(3) ?
C11 Se11 C1 N11 . . . . 18.1(2) ?
C11 Se11 C1 C2 . . . . -163.7(2) ?
N11 C1 C2 C3 . . . . 0.5(5) ?
Se11 C1 C2 C3 . . . . -177.6(2) ?
C1 C2 C3 C4 . . . . -2.2(5) ?
C2 C3 C4 C5 . . . . 1.9(5) ?
C1 N11 C5 C4 . . . . -1.6(4) ?
Pd1 N11 C5 C4 . . . . 175.4(2) ?
C3 C4 C5 N11 . . . . 0.0(5) ?
C10 N12 C6 C7 . . . . -1.3(4) ?
Pd2 N12 C6 C7 . . . . 179.37(18) ?
C10 N12 C6 C11 . . . . -177.4(2) ?
Pd2 N12 C6 C11 . . . . 3.3(3) ?
N12 C6 C7 C8 . . . . 0.5(4) ?
C11 C6 C7 C8 . . . . 176.3(2) ?
C6 C7 C8 C9 . . . . 0.1(4) ?
C7 C8 C9 C10 . . . . 0.0(4) ?
C6 N12 C10 C9 . . . . 1.5(4) ?
Pd2 N12 C10 C9 . . . . -179.1(2) ?
C8 C9 C10 N12 . . . . -0.9(5) ?
N12 C6 C11 Se11 . . . . -143.4(2) ?
C7 C6 C11 Se11 . . . . 40.7(3) ?
N12 C6 C11 Pd1 . . . . 93.3(2) ?
C7 C6 C11 Pd1 . . . . -82.6(3) ?
C16 N21 C12 C13 . . . . 2.7(4) ?
Pd2 N21 C12 C13 . . . . -177.4(2) ?
C16 N21 C12 Se21 . . . . -177.0(2) ?
Pd2 N21 C12 Se21 . . . . 2.9(3) ?
C22 Se21 C12 N21 . . . . 18.7(2) ?
C22 Se21 C12 C13 . . . . -161.0(3) ?
N21 C12 C13 C14 . . . . -1.1(5) ?
Se21 C12 C13 C14 . . . . 178.6(3) ?
C12 C13 C14 C15 . . . . -0.6(5) ?
C13 C14 C15 C16 . . . . 0.6(5) ?
C12 N21 C16 C15 . . . . -2.7(5) ?
Pd2 N21 C16 C15 . . . . 177.4(2) ?
C14 C15 C16 N21 . . . . 1.1(5) ?
C21 N22 C17 C18 . . . . 3.0(4) ?
Pd1 N22 C17 C18 . . . . -179.2(2) ?
C21 N22 C17 C22 . . . . -172.6(2) ?
Pd1 N22 C17 C22 . . . . 5.2(3) ?
N22 C17 C18 C19 . . . . -1.2(4) ?
C22 C17 C18 C19 . . . . 174.0(3) ?
C17 C18 C19 C20 . . . . -1.4(5) ?
C18 C19 C20 C21 . . . . 2.2(5) ?
C17 N22 C21 C20 . . . . -2.3(4) ?
Pd1 N22 C21 C20 . . . . 179.8(2) ?
C19 C20 C21 N22 . . . . -0.4(4) ?
N22 C17 C22 Se21 . . . . -144.3(2) ?
C18 C17 C22 Se21 . . . . 40.3(3) ?
N22 C17 C22 Pd2 . . . . 93.9(2) ?
C18 C17 C22 Pd2 . . . . -81.5(3) ?
Pd1 O1 C23 O2 . . . . -6.4(4) ?
Pd1 O1 C23 C24 . . . . 172.8(2) ?
Pd2 O4 C25 O5 . . . . -10.5(4) ?
Pd2 O4 C25 C26 . . . . 170.6(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 O2W . 0.95 2.6 3.550(4) 175.5 ?
C5 H5 O1 . 0.95 2.39 2.974(4) 119.7 ?
C7 H7 O2W 3_666 0.95 2.57 3.381(4) 143.6 ?
C9 H9 O5 1_565 0.95 2.39 3.262(4) 151.9 ?
C13 H13 O6W 2_545 0.95 2.59 3.277(4) 129.3 ?
C15 H15 O6W 4_566 0.95 2.63 3.496(5) 152.1 ?
C16 H16 O4 . 0.95 2.51 3.037(4) 114.7 ?
C16 H16 O5W 4_566 0.95 2.61 3.384(5) 139.2 ?
C21 H21 O2 . 0.95 2.6 3.147(4) 116.6 ?
C24 H24C Se11 4_575 0.98 2.98 3.681(3) 129.8 ?
O1W H1WA O2 1_545 0.830(16) 2.105(18) 2.922(3) 168.(3) ?
O1W H1WB O5 4_565 0.836(16) 1.890(17) 2.724(3) 175.(3) ?
O2W H2WA O3W 2_645 0.829(16) 1.912(17) 2.740(4) 180.(3) ?
O2W H2WB O2 1_545 0.824(16) 2.006(16) 2.820(3) 170.(3) ?
O3W H3WA O2W . 0.836(16) 1.947(19) 2.771(3) 168.(4) ?
O3W H3WB O1W . 0.838(16) 2.09(3) 2.844(3) 150.(4) ?
O4W H4WA O1 . 0.839(17) 2.02(2) 2.836(4) 166.(3) ?
O4W H4WB O1W . 0.850(17) 1.986(18) 2.833(4) 174.(3) ?
O5W H5WA O4W . 0.867(17) 1.900(18) 2.741(4) 163.(3) ?
O5W H5WB O7W 2_545 0.845(17) 2.21(2) 3.052(13) 171.(3) ?
O5W H5WB O8W . 0.845(17) 2.11(3) 2.791(12) 138.(3) ?
O6W H6WA O7W . 0.858(17) 2.14(3) 2.719(10) 125.(3) ?
O6W H6WA O8W 2 0.858(17) 1.83(2) 2.641(12) 156.(3) ?
O6W H6WB O4 4_575 0.845(17) 1.925(18) 2.762(4) 170.(4) ?



####################################################################### 
# 
# 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_compound_2a
_database_code_depnum_ccdc_archive 'CCDC 1844933'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H20 Cl4 Cu2 N4 Se2'
_chemical_formula_sum            'C22 H20 Cl4 Cu2 N4 Se2'
_chemical_formula_iupac          ?
_chemical_formula_weight         767.22

_chemical_melting_point          '414.15-415.15 K'

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7590(5)
_cell_length_b                   8.3854(6)
_cell_length_c                   11.2192(8)
_cell_angle_alpha                90.009(2)
_cell_angle_beta                 106.819(2)
_cell_angle_gamma                112.097(2)
_cell_volume                     642.49(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      2.6400
_cell_measurement_theta_max      30.5558
_cell_measurement_temperature    294.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.142
_exptl_crystal_density_diffrn    1.983
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             374

_exptl_absorpt_coefficient_mu    4.924
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS (version 2016/2; Bruker, 2016) was used to perform the multi--scan
absorption correction.
;
_exptl_absorpt_correction_T_min  0.40
_exptl_absorpt_correction_T_max  0.54

_exptl_special_details           
;
The Se1 & C11 atoms are positionally disordered. They were treated, allowing
their positions and occupancies to vary. Their anisotropic thermal parameters
either constrained to be equal (Se1 & C11A) or restrained to be similar (C11 &
Se1A). Furthermore to maintain a more planar phenyl ipso-C atom, FLAT & CHIV
were
applied.
;

_diffrn_ambient_temperature      294.(2)

_diffrn_source                   'microfocus X ray tube'
_diffrn_source_type              'Incoatex I\mS High Brilliance'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Incoatec Montel two dimensional X ray optics'

_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       '0.5 ° ω & φ scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            54520
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         30.63
_diffrn_reflns_theta_full        30.63
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             3929
_reflns_number_gt                3169
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0882
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.180
_refine_ls_number_reflns         3929
_refine_ls_number_parameters     167
_refine_ls_number_restraints     21
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+0.7664P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.546
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2016)'
_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  vim

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.53650(5) 0.52425(4) 0.24104(3) 0.03013(10) Uani d . . . 1.0 . .
Cl Cl1 0.78945(11) 0.72203(10) 0.39166(7) 0.04224(17) Uani d . . . 1.0 . .
Cl Cl2 0.30439(11) 0.34392(10) 0.07048(7) 0.04055(16) Uani d . . . 1.0 . .
N N1 0.6824(3) 0.3690(3) 0.2618(2) 0.0322(5) Uani d . . D 1.0 . .
C C1 0.6661(4) 0.2541(3) 0.3456(3) 0.0323(5) Uani d . . D 1.0 . .
Se Se1 0.49286(5) 0.24761(6) 0.43784(4) 0.03455(12) Uani d . P D 0.8336(14) A 1
C C11A 0.548(3) 0.257(3) 0.435(2) 0.03455(12) Uani d . P D 0.1664(14) A 2
H H11A 0.497796 0.1438 0.462666 0.041 Uiso calc U P R 0.1664(14) A 2
H H11B 0.437723 0.285998 0.391849 0.041 Uiso calc U P R 0.1664(14) A 2
C C5 0.7998(5) 0.3784(4) 0.1924(3) 0.0404(6) Uani d . . D 1.0 . .
H H5 0.810003 0.4567 0.133505 0.049 Uiso calc U . R 1.0 . .
C C2 0.7641(5) 0.1446(4) 0.3609(3) 0.0412(6) Uani d . . . 1.0 . .
H H2 0.748641 0.064457 0.418316 0.049 Uiso calc U . R 1.0 . .
C C3 0.8861(5) 0.1561(5) 0.2894(3) 0.0474(8) Uani d . . . 1.0 . .
H H3 0.953986 0.083785 0.298235 0.057 Uiso calc U . R 1.0 . .
C C4 0.9056(5) 0.2758(5) 0.2053(3) 0.0469(8) Uani d . . . 1.0 . .
H H4 0.989025 0.287376 0.157754 0.056 Uiso calc U . R 1.0 . .
N N2 0.3973(3) 0.6858(3) 0.2196(2) 0.0318(5) Uani d . . D 1.0 . .
C C6 0.2988(4) 0.7071(3) 0.2944(3) 0.0328(5) Uani d . . D 1.0 . .
Se Se1A 0.2633(6) 0.5536(4) 0.4071(4) 0.0325(7) Uani d U P D 0.1664(14) A 2
C C11 0.2994(12) 0.6096(7) 0.4086(8) 0.0360(15) Uani d U P D 0.8336(14) A 1
H H11C 0.319461 0.505079 0.393061 0.043 Uiso calc U P R 0.8336(14) A 1
H H11D 0.172853 0.575135 0.421973 0.043 Uiso calc U P R 0.8336(14) A 1
C C10 0.4084(5) 0.7804(4) 0.1231(3) 0.0405(6) Uani d . . D 1.0 . .
H H10 0.477713 0.766112 0.071589 0.049 Uiso calc U . R 1.0 . .
C C7 0.2028(5) 0.8198(4) 0.2712(3) 0.0436(7) Uani d . . . 1.0 . .
H H7 0.131386 0.830587 0.322292 0.052 Uiso calc U . R 1.0 . .
C C8 0.2144(5) 0.9151(4) 0.1720(3) 0.0446(7) Uani d . . . 1.0 . .
H H8 0.1506 0.990763 0.155216 0.054 Uiso calc U . R 1.0 . .
C C9 0.3209(5) 0.8976(4) 0.0978(3) 0.0444(7) Uani d . . . 1.0 . .
H H9 0.333764 0.963603 0.031834 0.053 Uiso calc U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 N1 . 1.996(2) ?
Cu1 N2 . 2.003(2) ?
Cu1 Cl1 . 2.2559(8) ?
Cu1 Cl2 . 2.2688(8) ?
N1 C5 . 1.342(4) ?
N1 C1 . 1.344(4) ?
C1 C2 . 1.378(4) ?
C1 C11A . 1.549(15) ?
C1 Se1 . 1.905(3) ?
Se1 C11 2_666 1.985(7) ?
C11A Se1A 2_666 2.13(2) ?
C11A H11A . 0.97 ?
C11A H11B . 0.97 ?
C5 C4 . 1.377(5) ?
C5 H5 . 0.93 ?
C2 C3 . 1.386(4) ?
C2 H2 . 0.93 ?
C3 C4 . 1.375(5) ?
C3 H3 . 0.93 ?
C4 H4 . 0.93 ?
N2 C6 . 1.339(3) ?
N2 C10 . 1.347(4) ?
C6 C7 . 1.390(4) ?
C6 C11 . 1.520(8) ?
C6 Se1A . 1.807(4) ?
C11 H11C . 0.97 ?
C11 H11D . 0.97 ?
C10 C9 . 1.378(4) ?
C10 H10 . 0.93 ?
C7 C8 . 1.375(5) ?
C7 H7 . 0.93 ?
C8 C9 . 1.374(5) ?
C8 H8 . 0.93 ?
C9 H9 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 Cu1 N2 . . 178.28(9) ?
N1 Cu1 Cl1 . . 89.67(7) ?
N2 Cu1 Cl1 . . 89.25(7) ?
N1 Cu1 Cl2 . . 90.08(7) ?
N2 Cu1 Cl2 . . 90.80(7) ?
Cl1 Cu1 Cl2 . . 171.96(3) ?
C5 N1 C1 . . 118.7(3) ?
C5 N1 Cu1 . . 120.3(2) ?
C1 N1 Cu1 . . 120.95(18) ?
N1 C1 C2 . . 122.0(3) ?
N1 C1 C11A . . 118.4(11) ?
C2 C1 C11A . . 119.4(11) ?
N1 C1 Se1 . . 115.7(2) ?
C2 C1 Se1 . . 122.3(2) ?
C1 Se1 C11 . 2_666 95.7(3) ?
C1 C11A Se1A . 2_666 108.6(11) ?
C1 C11A H11A . . 110.0 ?
Se1A C11A H11A 2_666 . 110.0 ?
C1 C11A H11B . . 110.0 ?
Se1A C11A H11B 2_666 . 110.0 ?
H11A C11A H11B . . 108.4 ?
N1 C5 C4 . . 122.2(3) ?
N1 C5 H5 . . 118.9 ?
C4 C5 H5 . . 118.9 ?
C1 C2 C3 . . 118.9(3) ?
C1 C2 H2 . . 120.6 ?
C3 C2 H2 . . 120.6 ?
C4 C3 C2 . . 119.1(3) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C3 C4 C5 . . 119.0(3) ?
C3 C4 H4 . . 120.5 ?
C5 C4 H4 . . 120.5 ?
C6 N2 C10 . . 118.9(2) ?
C6 N2 Cu1 . . 124.98(19) ?
C10 N2 Cu1 . . 116.11(19) ?
N2 C6 C7 . . 121.2(3) ?
N2 C6 C11 . . 118.5(4) ?
C7 C6 C11 . . 120.3(4) ?
N2 C6 Se1A . . 115.3(2) ?
C7 C6 Se1A . . 122.6(3) ?
C6 Se1A C11A . 2_666 94.0(7) ?
C6 C11 Se1 . 2_666 112.0(3) ?
C6 C11 H11C . . 109.2 ?
Se1 C11 H11C 2_666 . 109.2 ?
C6 C11 H11D . . 109.2 ?
Se1 C11 H11D 2_666 . 109.2 ?
H11C C11 H11D . . 107.9 ?
N2 C10 C9 . . 122.4(3) ?
N2 C10 H10 . . 118.8 ?
C9 C10 H10 . . 118.8 ?
C8 C7 C6 . . 119.4(3) ?
C8 C7 H7 . . 120.3 ?
C6 C7 H7 . . 120.3 ?
C9 C8 C7 . . 119.4(3) ?
C9 C8 H8 . . 120.3 ?
C7 C8 H8 . . 120.3 ?
C8 C9 C10 . . 118.7(3) ?
C8 C9 H9 . . 120.7 ?
C10 C9 H9 . . 120.7 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . -0.8(4) ?
Cu1 N1 C1 C2 . . . . 179.5(2) ?
C5 N1 C1 C11A . . . . 173.7(10) ?
Cu1 N1 C1 C11A . . . . -6.0(10) ?
C5 N1 C1 Se1 . . . . -179.0(2) ?
Cu1 N1 C1 Se1 . . . . 1.3(3) ?
N1 C1 C11A Se1A . . . 2_666 -84.9(13) ?
C2 C1 C11A Se1A . . . 2_666 89.8(13) ?
C1 N1 C5 C4 . . . . -0.8(4) ?
Cu1 N1 C5 C4 . . . . 178.9(2) ?
N1 C1 C2 C3 . . . . 1.3(4) ?
C11A C1 C2 C3 . . . . -173.2(10) ?
Se1 C1 C2 C3 . . . . 179.3(2) ?
C1 C2 C3 C4 . . . . -0.1(5) ?
C2 C3 C4 C5 . . . . -1.5(5) ?
N1 C5 C4 C3 . . . . 2.0(5) ?
C10 N2 C6 C7 . . . . 2.4(4) ?
Cu1 N2 C6 C7 . . . . -178.7(2) ?
C10 N2 C6 C11 . . . . -175.6(4) ?
Cu1 N2 C6 C11 . . . . 3.3(4) ?
C10 N2 C6 Se1A . . . . 171.7(3) ?
Cu1 N2 C6 Se1A . . . . -9.4(3) ?
N2 C6 Se1A C11A . . . 2_666 111.8(6) ?
C7 C6 Se1A C11A . . . 2_666 -79.0(6) ?
N2 C6 C11 Se1 . . . 2_666 94.7(5) ?
C7 C6 C11 Se1 . . . 2_666 -83.3(5) ?
C6 N2 C10 C9 . . . . -0.5(5) ?
Cu1 N2 C10 C9 . . . . -179.5(3) ?
N2 C6 C7 C8 . . . . -2.1(5) ?
C11 C6 C7 C8 . . . . 175.9(4) ?
Se1A C6 C7 C8 . . . . -170.6(3) ?
C6 C7 C8 C9 . . . . -0.2(5) ?
C7 C8 C9 C10 . . . . 2.0(5) ?
N2 C10 C9 C8 . . . . -1.7(5) ?



####################################################################### 
# 
# 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_compound_2b
_database_code_depnum_ccdc_archive 'CCDC 1844934'
_audit_update_record             
;
2018-05-23 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C11 H10 Cl2 Cu N2  Se'
_chemical_formula_sum            'C11 H10 Cl2 Cu N2 Se'
_chemical_formula_iupac          ?
_chemical_formula_weight         383.61

_chemical_melting_point          '399.15-401.15 K'

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9883(4)
_cell_length_b                   7.3034(4)
_cell_length_c                   14.1926(8)
_cell_angle_alpha                77.7050(17)
_cell_angle_beta                 81.6484(17)
_cell_angle_gamma                63.8415(15)
_cell_volume                     634.17(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    720
_cell_measurement_theta_min      2.4511
_cell_measurement_theta_max      25.5649
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       'triangular plate'
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.048
_exptl_crystal_density_diffrn    2.009
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             374

_exptl_absorpt_coefficient_mu    2.625
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
SADABS (version 2014/5; Bruker, 2014) was used to perform the
absorption correction based on the face index crystal dimensions.
;
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.88

_exptl_special_details           
;
During indexing, a second diffraction pattern with noted. This was separated
from the principal diffraction
pattern and indexed to the same cell, but related by a rotation of about 8 °
about the real c axis from the
principal cell. It is presumed to be from a small crystal fragment joined to
the main crystal. Integration used
both cells. During scaling and adsorption correction, it was noted that the
smaller crystal has just about
10% the average I/σ(I) of the main crystal. Only the data for the main crystal
were processed and saved.
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus X ray tube'
_diffrn_source_type              'Incoatex I\mS High Brilliance'

_diffrn_radiation_type           'Ag K\a'
_diffrn_radiation_wavelength     0.56086
_diffrn_radiation_monochromator  'Incoatec Montel two dimensional X ray optics'

_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       '0.5 ° ω & φ scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            8907
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.64
_diffrn_reflns_theta_full        25.64
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             4843
_reflns_number_gt                4134
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0916
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_restrained_S_all      1.191
_refine_ls_number_reflns         4843
_refine_ls_number_parameters     161
_refine_ls_number_restraints     5
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+2.0050P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.912
_refine_diff_density_min         -0.776
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.0998 0.0984 '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'
N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se 0.2367 1.4831 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3240 0.8257 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 v2015.5-2 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 758)'
_computing_publication_material  vim

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se Se1 0.58664(5) 0.85188(8) 0.30201(3) 0.01735(10) Uani d . P D 0.8674(15) A 1
Se Se1A 0.7294(5) 0.6247(7) 0.2383(3) 0.0157(7) Uani d . P D 0.1326(15) A 2
Cu Cu1 0.21970(5) 0.74592(5) 0.24177(2) 0.01489(8) Uani d . . . 1.0 . .
Cl Cl1 -0.02787(11) 1.06476(11) 0.19842(5) 0.02268(14) Uani d . . . 1.0 . .
Cl Cl2 0.26879(12) 0.41590(11) 0.27431(5) 0.02135(14) Uani d . . . 1.0 . .
N N1 0.2360(4) 0.7582(4) 0.37971(17) 0.0158(4) Uani d . . . 1.0 . .
N N13 0.4035(4) 0.7307(4) 0.11979(17) 0.0158(4) Uani d . . . 1.0 . .
C C2 0.0993(4) 0.7246(4) 0.4513(2) 0.0189(5) Uani d . . . 1.0 . .
H H2 -0.0093 0.6927 0.436 0.023 Uiso calc U . R 1.0 . .
C C3 0.1124(5) 0.7351(4) 0.5461(2) 0.0206(5) Uani d . . . 1.0 . .
H H3 0.0109 0.7162 0.5947 0.025 Uiso calc U . R 1.0 . .
C C4 0.2758(5) 0.7737(4) 0.5690(2) 0.0213(5) Uani d . . . 1.0 . .
H H4 0.2862 0.7847 0.6333 0.026 Uiso calc U . R 1.0 . .
C C5 0.4246(5) 0.7961(4) 0.4962(2) 0.0205(5) Uani d . . . 1.0 . .
H H5 0.5431 0.8137 0.511 0.025 Uiso calc U . R 1.0 . .
C C6 0.3973(4) 0.7924(4) 0.4013(2) 0.0173(5) Uani d . . D 1.0 . .
C C7 0.6847(9) 0.6153(12) 0.2316(5) 0.0157(7) Uani d . P D 0.8674(15) A 1
H H7A 0.8426 0.5455 0.229 0.019 Uiso calc U P R 0.8674(15) A 1
H H7B 0.6308 0.5142 0.2681 0.019 Uiso calc U P R 0.8674(15) A 1
C C7A 0.542(5) 0.868(5) 0.306(2) 0.01735(10) Uani d . P D 0.1326(15) A 2
H H7AA 0.6314 0.9209 0.3296 0.021 Uiso calc U P R 0.1326(15) A 2
H H7AB 0.4433 0.9817 0.2601 0.021 Uiso calc U P R 0.1326(15) A 2
C C8 0.6112(4) 0.6780(4) 0.1293(2) 0.0179(5) Uani d . . D 1.0 . .
C C9 0.7512(5) 0.6783(5) 0.0492(2) 0.0232(6) Uani d . . . 1.0 . .
H H9 0.896 0.6454 0.0572 0.028 Uiso calc U . R 1.0 . .
C C10 0.6778(5) 0.7271(5) -0.0426(2) 0.0237(6) Uani d . . . 1.0 . .
H H10 0.7718 0.7268 -0.0982 0.028 Uiso calc U . R 1.0 . .
C C11 0.4649(5) 0.7764(4) -0.0522(2) 0.0215(5) Uani d . . . 1.0 . .
H H11 0.4112 0.8079 -0.1142 0.026 Uiso calc U . R 1.0 . .
C C12 0.3314(5) 0.7787(4) 0.0313(2) 0.0189(5) Uani d . . . 1.0 . .
H H12 0.1848 0.8155 0.0251 0.023 Uiso calc U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Se1 C6 . 1.905(3) ?
Se1 C7 . 1.987(8) ?
Se1A C8 . 1.748(5) ?
Se1A C7A . 2.030(17) ?
Cu1 N13 . 1.992(2) ?
Cu1 N1 . 2.001(2) ?
Cu1 Cl1 . 2.2229(8) ?
Cu1 Cl2 . 2.2323(8) ?
N1 C6 . 1.345(4) ?
N1 C2 . 1.350(4) ?
N13 C12 . 1.340(4) ?
N13 C8 . 1.347(4) ?
C2 C3 . 1.381(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.386(5) ?
C3 H3 . 0.95 ?
C4 C5 . 1.393(4) ?
C4 H4 . 0.95 ?
C5 C6 . 1.395(4) ?
C5 H5 . 0.95 ?
C6 C7A . 1.71(4) ?
C7 C8 . 1.518(7) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C7A H7AA . 0.99 ?
C7A H7AB . 0.99 ?
C8 C9 . 1.388(4) ?
C9 C10 . 1.387(5) ?
C9 H9 . 0.95 ?
C10 C11 . 1.388(5) ?
C10 H10 . 0.95 ?
C11 C12 . 1.395(4) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 Se1 C7 . . 101.9(2) ?
C8 Se1A C7A . . 104.9(9) ?
N13 Cu1 N1 . . 137.76(10) ?
N13 Cu1 Cl1 . . 96.96(7) ?
N1 Cu1 Cl1 . . 98.89(7) ?
N13 Cu1 Cl2 . . 97.68(7) ?
N1 Cu1 Cl2 . . 93.48(7) ?
Cl1 Cu1 Cl2 . . 141.84(3) ?
C6 N1 C2 . . 119.4(2) ?
C6 N1 Cu1 . . 117.55(19) ?
C2 N1 Cu1 . . 123.0(2) ?
C12 N13 C8 . . 119.4(2) ?
C12 N13 Cu1 . . 124.32(19) ?
C8 N13 Cu1 . . 116.15(19) ?
N1 C2 C3 . . 122.1(3) ?
N1 C2 H2 . . 118.9 ?
C3 C2 H2 . . 118.9 ?
C2 C3 C4 . . 118.9(3) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C3 C4 C5 . . 119.0(3) ?
C3 C4 H4 . . 120.5 ?
C5 C4 H4 . . 120.5 ?
C4 C5 C6 . . 119.1(3) ?
C4 C5 H5 . . 120.4 ?
C6 C5 H5 . . 120.4 ?
N1 C6 C5 . . 121.2(3) ?
N1 C6 C7A . . 116.7(10) ?
C5 C6 C7A . . 121.4(10) ?
N1 C6 Se1 . . 120.8(2) ?
C5 C6 Se1 . . 117.9(2) ?
C8 C7 Se1 . . 113.5(4) ?
C8 C7 H7A . . 108.9 ?
Se1 C7 H7A . . 108.9 ?
C8 C7 H7B . . 108.9 ?
Se1 C7 H7B . . 108.9 ?
H7A C7 H7B . . 107.7 ?
C6 C7A Se1A . . 110.(2) ?
C6 C7A H7AA . . 109.8 ?
Se1A C7A H7AA . . 109.8 ?
C6 C7A H7AB . . 109.8 ?
Se1A C7A H7AB . . 109.8 ?
H7AA C7A H7AB . . 108.2 ?
N13 C8 C9 . . 121.4(3) ?
N13 C8 C7 . . 116.8(3) ?
C9 C8 C7 . . 121.8(3) ?
N13 C8 Se1A . . 125.6(2) ?
C9 C8 Se1A . . 112.8(3) ?
C10 C9 C8 . . 119.4(3) ?
C10 C9 H9 . . 120.3 ?
C8 C9 H9 . . 120.3 ?
C9 C10 C11 . . 119.0(3) ?
C9 C10 H10 . . 120.5 ?
C11 C10 H10 . . 120.5 ?
C10 C11 C12 . . 118.6(3) ?
C10 C11 H11 . . 120.7 ?
C12 C11 H11 . . 120.7 ?
N13 C12 C11 . . 122.1(3) ?
N13 C12 H12 . . 119.0 ?
C11 C12 H12 . . 119.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N13 Cu1 N1 C6 . . . . 11.2(3) ?
Cl1 Cu1 N1 C6 . . . . -99.58(19) ?
Cl2 Cu1 N1 C6 . . . . 116.64(19) ?
N13 Cu1 N1 C2 . . . . -165.71(19) ?
Cl1 Cu1 N1 C2 . . . . 83.5(2) ?
Cl2 Cu1 N1 C2 . . . . -60.3(2) ?
N1 Cu1 N13 C12 . . . . -161.4(2) ?
Cl1 Cu1 N13 C12 . . . . -49.9(2) ?
Cl2 Cu1 N13 C12 . . . . 94.7(2) ?
N1 Cu1 N13 C8 . . . . 15.2(3) ?
Cl1 Cu1 N13 C8 . . . . 126.65(19) ?
Cl2 Cu1 N13 C8 . . . . -88.7(2) ?
C6 N1 C2 C3 . . . . 3.6(4) ?
Cu1 N1 C2 C3 . . . . -179.6(2) ?
N1 C2 C3 C4 . . . . -2.5(4) ?
C2 C3 C4 C5 . . . . -1.4(4) ?
C3 C4 C5 C6 . . . . 4.1(4) ?
C2 N1 C6 C5 . . . . -0.7(4) ?
Cu1 N1 C6 C5 . . . . -177.8(2) ?
C2 N1 C6 C7A . . . . -171.3(11) ?
Cu1 N1 C6 C7A . . . . 11.6(11) ?
C2 N1 C6 Se1 . . . . -177.4(2) ?
Cu1 N1 C6 Se1 . . . . 5.6(3) ?
C4 C5 C6 N1 . . . . -3.1(4) ?
C4 C5 C6 C7A . . . . 167.1(12) ?
C4 C5 C6 Se1 . . . . 173.6(2) ?
C7 Se1 C6 N1 . . . . -53.7(3) ?
C7 Se1 C6 C5 . . . . 129.6(3) ?
C6 Se1 C7 C8 . . . . 113.9(3) ?
N1 C6 C7A Se1A . . . . -72.8(16) ?
C5 C6 C7A Se1A . . . . 116.6(10) ?
C8 Se1A C7A C6 . . . . 107.7(14) ?
C12 N13 C8 C9 . . . . 1.9(4) ?
Cu1 N13 C8 C9 . . . . -174.8(2) ?
C12 N13 C8 C7 . . . . -177.1(4) ?
Cu1 N13 C8 C7 . . . . 6.1(4) ?
C12 N13 C8 Se1A . . . . 176.3(3) ?
Cu1 N13 C8 Se1A . . . . -0.5(4) ?
Se1 C7 C8 N13 . . . . -73.6(4) ?
Se1 C7 C8 C9 . . . . 107.3(4) ?
C7A Se1A C8 N13 . . . . -50.8(13) ?
C7A Se1A C8 C9 . . . . 124.0(13) ?
N13 C8 C9 C10 . . . . -2.2(4) ?
C7 C8 C9 C10 . . . . 176.8(4) ?
Se1A C8 C9 C10 . . . . -177.2(3) ?
C8 C9 C10 C11 . . . . 0.6(5) ?
C9 C10 C11 C12 . . . . 1.2(4) ?
C8 N13 C12 C11 . . . . -0.1(4) ?
Cu1 N13 C12 C11 . . . . 176.4(2) ?
C10 C11 C12 N13 . . . . -1.5(4) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C3 H3 Cl2 2_566 0.95 2.84 3.772(3) 168.4 ?
C7 H7A Cl2 1_655 0.99 2.83 3.775(5) 160.8 ?
C7 H7B Cl2 . 0.99 2.90 3.712(5) 139.4 ?
C7A H7AB Cl2 1_565 0.99 2.89 3.55(3) 124.3 ?
C11 H11 Cl1 2_575 0.95 2.78 3.560(3) 139.9 ?



####################################################################### 
# 
# 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_compound_4
_database_code_depnum_ccdc_archive 'CCDC 1844938'
_audit_update_record             
;
2018-05-23 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 Cu2 I2 N2 Se'
_chemical_formula_sum            'C11 H10 Cu2 I2 N2 Se'
_chemical_formula_iupac          ?
_chemical_formula_weight         630.05
_chemical_absolute_configuration ad

_chemical_melting_point          '452.15-454.15 K'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5828(3)
_cell_length_b                   8.4187(3)
_cell_length_c                   9.7002(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.0880(10)
_cell_angle_gamma                90
_cell_volume                     755.58(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.2011
_cell_measurement_theta_max      30.4231
_cell_measurement_temperature    295.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.091
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.058
_exptl_crystal_density_diffrn    2.769
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576

_exptl_absorpt_coefficient_mu    9.291
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS (version 2016/2; Bruker, 2016) was used to perform the multi--scan
absorption correction.
;
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_T_max  0.61

_exptl_special_details           
;
;

_diffrn_ambient_temperature      295.(2)

_diffrn_source                   'microfocus X ray tube'
_diffrn_source_type              'Incoatex I\mS High Brilliance'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Incoatec Montel two dimensional X ray optics'

_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       '0.5 ° ω & φ scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            32101
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_full        30.57
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;

Refined as a 2-component inversion twin.
;

_reflns_number_total             4626
_reflns_number_gt                4274
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0189
_refine_ls_wR_factor_gt          0.0340
_refine_ls_wR_factor_ref         0.0352
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_number_reflns         4626
_refine_ls_number_parameters     164
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0149P)²+0.3986P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.818
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.494(11)

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2016)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
'Diamond (version 3.2k; Crystal Impact GbR, Bonn, Germany)'
_computing_publication_material  vim

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.18920(3) 0.40559(4) 0.24097(3) 0.03653(7) Uani d . . . 1 . .
I I2 0.58328(3) 0.49223(3) 0.58466(3) 0.03222(6) Uani d . . . 1 . .
Se Se1 0.19194(4) 0.71542(5) 0.57055(4) 0.02968(8) Uani d . . . 1 . .
Cu Cu1 0.30546(6) 0.45697(7) 0.50928(6) 0.04108(14) Uani d . . . 1 . .
Cu Cu2 0.54102(6) 0.80880(7) 0.63873(6) 0.04064(13) Uani d . . . 1 . .
N N1 0.2023(4) 0.3517(4) 0.6450(3) 0.0318(7) Uani d . . . 1 . .
N N2 0.4258(3) 0.8025(4) 0.7896(3) 0.0304(7) Uani d . . . 1 . .
C C1 0.0900(4) 0.4282(5) 0.6752(4) 0.0292(8) Uani d . . . 1 . .
C C2 0.0263(5) 0.3740(6) 0.7794(5) 0.0411(10) Uani d . . . 1 . .
H H2 -0.05078 0.42837 0.799005 0.049 Uiso calc U . R 1 . .
C C3 0.0798(6) 0.2372(6) 0.8537(5) 0.0491(12) Uani d . . . 1 . .
H H3 0.040094 0.199548 0.925231 0.059 Uiso calc U . R 1 . .
C C4 0.1912(6) 0.1580(6) 0.8212(5) 0.0488(12) Uani d . . . 1 . .
H H4 0.2277 0.065369 0.869423 0.059 Uiso calc U . R 1 . .
C C5 0.2488(5) 0.2179(5) 0.7153(5) 0.0394(9) Uani d . . . 1 . .
H H5 0.323417 0.162256 0.692061 0.047 Uiso calc U . R 1 . .
C C6 0.2897(4) 0.7518(4) 0.7675(4) 0.0256(7) Uani d . . . 1 . .
C C7 0.2241(5) 0.7315(5) 0.8776(4) 0.0360(9) Uani d . . . 1 . .
H H7 0.130089 0.692834 0.858818 0.043 Uiso calc U . R 1 . .
C C8 0.2985(5) 0.7688(6) 1.0143(5) 0.0426(10) Uani d . . . 1 . .
H H8 0.256914 0.75438 1.089955 0.051 Uiso calc U . R 1 . .
C C9 0.4361(5) 0.8281(7) 1.0369(5) 0.0466(11) Uani d . . . 1 . .
H H9 0.487977 0.857995 1.128124 0.056 Uiso calc U . R 1 . .
C C10 0.4968(5) 0.8428(6) 0.9234(4) 0.0429(11) Uani d . . . 1 . .
H H10 0.590371 0.882165 0.940153 0.051 Uiso calc U . R 1 . .
C C11 0.0357(4) 0.5754(5) 0.5919(5) 0.0338(9) Uani d . . . 1 . .
H H11A -0.025937 0.633044 0.639634 0.041 Uiso calc U . R 1 . .
H H11B -0.022577 0.545365 0.497972 0.041 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 Cu1 . 2.5870(6) ?
I1 Cu2 2_646 2.6718(6) ?
I2 Cu1 . 2.5879(6) ?
I2 Cu2 2_646 2.6750(6) ?
I2 Cu2 . 2.7663(7) ?
Se1 C6 . 1.921(4) ?
Se1 C11 . 1.959(4) ?
Se1 Cu1 . 2.5705(7) ?
Cu1 N1 . 2.043(3) ?
Cu1 Cu2 2_646 2.6232(7) ?
Cu2 N2 . 2.050(3) ?
N1 C5 . 1.332(6) ?
N1 C1 . 1.350(5) ?
N2 C6 . 1.336(5) ?
N2 C10 . 1.343(5) ?
C1 C2 . 1.387(5) ?
C1 C11 . 1.497(6) ?
C2 C3 . 1.384(7) ?
C2 H2 . 0.93 ?
C3 C4 . 1.362(8) ?
C3 H3 . 0.93 ?
C4 C5 . 1.382(7) ?
C4 H4 . 0.93 ?
C5 H5 . 0.93 ?
C6 C7 . 1.384(5) ?
C7 C8 . 1.369(6) ?
C7 H7 . 0.93 ?
C8 C9 . 1.373(7) ?
C8 H8 . 0.93 ?
C9 C10 . 1.378(6) ?
C9 H9 . 0.93 ?
C10 H10 . 0.93 ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cu1 I1 Cu2 . 2_646 59.818(17) ?
Cu1 I2 Cu2 . 2_646 59.767(17) ?
Cu1 I2 Cu2 . . 88.482(18) ?
Cu2 I2 Cu2 2_646 . 130.804(15) ?
C6 Se1 C11 . . 100.33(17) ?
C6 Se1 Cu1 . . 103.82(11) ?
C11 Se1 Cu1 . . 84.04(13) ?
N1 Cu1 Se1 . . 85.03(10) ?
N1 Cu1 I1 . . 114.96(10) ?
Se1 Cu1 I1 . . 106.07(2) ?
N1 Cu1 I2 . . 120.16(10) ?
Se1 Cu1 I2 . . 107.68(2) ?
I1 Cu1 I2 . . 116.45(2) ?
N1 Cu1 Cu2 . 2_646 125.51(10) ?
Se1 Cu1 Cu2 . 2_646 149.37(3) ?
I1 Cu1 Cu2 . 2_646 61.697(18) ?
I2 Cu1 Cu2 . 2_646 61.767(18) ?
N2 Cu2 Cu1 . 2_656 152.35(11) ?
N2 Cu2 I1 . 2_656 109.62(10) ?
Cu1 Cu2 I1 2_656 2_656 58.484(18) ?
N2 Cu2 I2 . 2_656 112.59(10) ?
Cu1 Cu2 I2 2_656 2_656 58.467(18) ?
I1 Cu2 I2 2_656 2_656 110.73(2) ?
N2 Cu2 I2 . . 104.06(10) ?
Cu1 Cu2 I2 2_656 . 102.93(2) ?
I1 Cu2 I2 2_656 . 101.76(2) ?
I2 Cu2 I2 2_656 . 117.31(2) ?
C5 N1 C1 . . 118.2(4) ?
C5 N1 Cu1 . . 122.9(3) ?
C1 N1 Cu1 . . 118.6(3) ?
C6 N2 C10 . . 117.6(3) ?
C6 N2 Cu2 . . 125.4(3) ?
C10 N2 Cu2 . . 116.9(3) ?
N1 C1 C2 . . 121.8(4) ?
N1 C1 C11 . . 117.6(3) ?
C2 C1 C11 . . 120.6(4) ?
C3 C2 C1 . . 118.7(4) ?
C3 C2 H2 . . 120.7 ?
C1 C2 H2 . . 120.7 ?
C4 C3 C2 . . 119.5(4) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C3 C4 C5 . . 118.8(5) ?
C3 C4 H4 . . 120.6 ?
C5 C4 H4 . . 120.6 ?
N1 C5 C4 . . 122.9(4) ?
N1 C5 H5 . . 118.5 ?
C4 C5 H5 . . 118.5 ?
N2 C6 C7 . . 122.5(4) ?
N2 C6 Se1 . . 114.4(3) ?
C7 C6 Se1 . . 123.1(3) ?
C8 C7 C6 . . 119.5(4) ?
C8 C7 H7 . . 120.3 ?
C6 C7 H7 . . 120.3 ?
C7 C8 C9 . . 118.3(4) ?
C7 C8 H8 . . 120.8 ?
C9 C8 H8 . . 120.8 ?
C8 C9 C10 . . 119.5(4) ?
C8 C9 H9 . . 120.2 ?
C10 C9 H9 . . 120.2 ?
N2 C10 C9 . . 122.5(4) ?
N2 C10 H10 . . 118.8 ?
C9 C10 H10 . . 118.8 ?
C1 C11 Se1 . . 112.8(3) ?
C1 C11 H11A . . 109.0 ?
Se1 C11 H11A . . 109.0 ?
C1 C11 H11B . . 109.0 ?
Se1 C11 H11B . . 109.0 ?
H11A C11 H11B . . 107.8 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . 2.1(6) ?
Cu1 N1 C1 C2 . . . . -171.9(3) ?
C5 N1 C1 C11 . . . . -177.9(4) ?
Cu1 N1 C1 C11 . . . . 8.1(4) ?
N1 C1 C2 C3 . . . . -0.2(6) ?
C11 C1 C2 C3 . . . . 179.8(4) ?
C1 C2 C3 C4 . . . . -1.2(7) ?
C2 C3 C4 C5 . . . . 0.6(7) ?
C1 N1 C5 C4 . . . . -2.7(6) ?
Cu1 N1 C5 C4 . . . . 171.0(4) ?
C3 C4 C5 N1 . . . . 1.4(7) ?
C10 N2 C6 C7 . . . . -3.7(6) ?
Cu2 N2 C6 C7 . . . . 171.6(3) ?
C10 N2 C6 Se1 . . . . 174.7(3) ?
Cu2 N2 C6 Se1 . . . . -10.1(4) ?
N2 C6 C7 C8 . . . . 2.0(6) ?
Se1 C6 C7 C8 . . . . -176.2(3) ?
C6 C7 C8 C9 . . . . 1.1(7) ?
C7 C8 C9 C10 . . . . -2.3(8) ?
C6 N2 C10 C9 . . . . 2.4(7) ?
Cu2 N2 C10 C9 . . . . -173.3(4) ?
C8 C9 C10 N2 . . . . 0.6(8) ?
N1 C1 C11 Se1 . . . . -43.9(4) ?
C2 C1 C11 Se1 . . . . 136.1(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C9 H9 I2 2_657 0.93 3.24 3.972(5) 137.1 ?
C10 H10 I1 2_656 0.93 3.09 3.792(5) 134.1 ?
C11 H11A I1 2_556 0.97 3.16 4.101(4) 163.5 ?



####################################################################### 
# 
# 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_compound_3
_database_code_depnum_ccdc_archive 'CCDC 1844937'
_audit_update_record             
;
2018-05-23 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Cu(NC5H4CH2SeC5N)I2
_chemical_formula_moiety         'C22 H20 Cu2 I2 N4 Se2'
_chemical_formula_sum            'C22 H20 Cu2 I2 N4 Se2'
_chemical_formula_iupac          ?
_chemical_formula_weight         879.22

_chemical_melting_point          '438.15-440.15 K'

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8651(4)
_cell_length_b                   9.3649(5)
_cell_length_c                   9.9211(5)
_cell_angle_alpha                87.404(2)
_cell_angle_beta                 71.217(2)
_cell_angle_gamma                71.497(2)
_cell_volume                     654.75(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    834
_cell_measurement_theta_min      2.1491
_cell_measurement_theta_max      27.2863
_cell_measurement_temperature    294.(2)

_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    2.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412

_exptl_absorpt_coefficient_mu    6.779
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS (version 2016/2; Bruker, 2016) was used to perform the multi--scan
absorption correction.
Values from SABADS output file and are estimated. Their ratio is more
reliable.
;
_exptl_absorpt_correction_T_min  0.4059
_exptl_absorpt_correction_T_max  0.7461

_exptl_special_details           
;
;

_diffrn_ambient_temperature      294.(2)

_diffrn_source                   'microfocus X ray tube'
_diffrn_source_type              'Incoatex I\mS High Brilliance'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Incoatec Montel two dimensional X ray optics'

_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       '0.5 ° ω & φ scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            52788
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         30.67
_diffrn_reflns_theta_full        30.67
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             4040
_reflns_number_gt                3324
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0677
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.157
_refine_ls_number_reflns         4040
_refine_ls_number_parameters     158
_refine_ls_number_restraints     23
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0150P)²+1.4023P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.254
_refine_diff_density_min         -1.201
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2016)'
_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  vim

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.35953(3) 0.34808(2) 0.12322(2) 0.03776(7) Uani d . . . 1.0 . .
Cu Cu1 0.39040(7) 0.62009(5) 0.13157(5) 0.04412(11) Uani d . . . 1.0 . .
N N1 0.5316(4) 0.6227(3) 0.2744(3) 0.0391(6) Uani d . . D 1.0 . .
C C1 0.4813(5) 0.7238(5) 0.3826(4) 0.0454(8) Uani d . . D 1.0 . .
Se Se1 0.26572(8) 0.90310(7) 0.41555(6) 0.0651(2) Uani d . P D 0.8585(19) A 1
C C11A 0.272(3) 0.829(3) 0.414(3) 0.0651(2) Uani d . P D 0.1415(19) A 2
H H11C 0.224549 0.878073 0.509049 0.078 Uiso calc U P R 0.1415(19) A 2
H H11D 0.192279 0.770658 0.409153 0.078 Uiso calc U P R 0.1415(19) A 2
C C2 0.5822(7) 0.7075(6) 0.4766(4) 0.0658(13) Uani d . . D 1.0 . .
H H2 0.544851 0.780878 0.549686 0.079 Uiso calc U . R 1.0 . .
C C3 0.7373(7) 0.5826(7) 0.4613(5) 0.0695(14) Uani d . . . 1.0 . .
H H3 0.803565 0.567898 0.526064 0.083 Uiso calc U . R 1.0 . .
C C4 0.7937(6) 0.4791(6) 0.3484(5) 0.0586(11) Uani d . . . 1.0 . .
H H4 0.900865 0.394705 0.333581 0.07 Uiso calc U . R 1.0 . .
C C5 0.6883(6) 0.5033(5) 0.2586(4) 0.0475(8) Uani d . . . 1.0 . .
H H5 0.727178 0.433259 0.1823 0.057 Uiso calc U . R 1.0 . .
N N2 0.1356(4) 0.7765(3) 0.1527(3) 0.0354(6) Uani d . . D 1.0 . .
C C6 0.1020(5) 0.9202(4) 0.1928(3) 0.0382(7) Uani d . . D 1.0 . .
Se Se1A 0.2659(8) 0.9778(6) 0.2763(7) 0.0703(19) Uani d U P D 0.1415(19) A 2
C C11 0.2634(12) 0.9511(7) 0.2232(9) 0.0525(17) Uani d U P D 0.8585(19) A 1
H H11A 0.252055 1.056721 0.211168 0.063 Uiso calc U P R 0.8585(19) A 1
H H11B 0.382449 0.891425 0.154992 0.063 Uiso calc U P R 0.8585(19) A 1
C C7 -0.0664(6) 1.0317(4) 0.1994(4) 0.0508(9) Uani d . . D 1.0 . .
H H7 -0.086034 1.130995 0.226181 0.061 Uiso calc U . R 1.0 . .
C C8 -0.2044(6) 0.9942(5) 0.1661(5) 0.0560(11) Uani d . . . 1.0 . .
H H8 -0.318289 1.067762 0.170226 0.067 Uiso calc U . R 1.0 . .
C C9 -0.1717(5) 0.8477(5) 0.1268(4) 0.0501(9) Uani d . . . 1.0 . .
H H9 -0.263212 0.819609 0.104279 0.06 Uiso calc U . R 1.0 . .
C C10 -0.0009(5) 0.7418(4) 0.1210(4) 0.0415(7) Uani d . . . 1.0 . .
H H10 0.020729 0.642119 0.09395 0.05 Uiso calc U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 Cu1 . 2.6419(5) ?
I1 Cu1 2_665 2.7293(6) ?
Cu1 N2 . 2.025(3) ?
Cu1 N1 . 2.067(3) ?
N1 C1 . 1.336(4) ?
N1 C5 . 1.346(5) ?
C1 C2 . 1.382(5) ?
C1 C11A . 1.564(17) ?
C1 Se1 . 1.920(4) ?
Se1 C11 . 1.946(8) ?
C11A Se1A . 1.90(3) ?
C11A H11C . 0.97 ?
C11A H11D . 0.97 ?
C2 C3 . 1.367(7) ?
C2 H2 . 0.93 ?
C3 C4 . 1.378(7) ?
C3 H3 . 0.93 ?
C4 C5 . 1.367(6) ?
C4 H4 . 0.93 ?
C5 H5 . 0.93 ?
N2 C6 . 1.339(4) ?
N2 C10 . 1.344(4) ?
C6 C7 . 1.386(5) ?
C6 C11 . 1.508(8) ?
C6 Se1A . 1.952(7) ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
C7 C8 . 1.376(6) ?
C7 H7 . 0.93 ?
C8 C9 . 1.365(6) ?
C8 H8 . 0.93 ?
C9 C10 . 1.379(5) ?
C9 H9 . 0.93 ?
C10 H10 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cu1 I1 Cu1 . 2_665 72.195(17) ?
N2 Cu1 N1 . . 120.69(12) ?
N2 Cu1 I1 . . 109.07(8) ?
N1 Cu1 I1 . . 107.61(8) ?
N2 Cu1 I1 . 2_665 108.04(8) ?
N1 Cu1 I1 . 2_665 102.91(8) ?
I1 Cu1 I1 . 2_665 107.806(17) ?
C1 N1 C5 . . 117.1(3) ?
C1 N1 Cu1 . . 128.0(3) ?
C5 N1 Cu1 . . 114.9(2) ?
N1 C1 C2 . . 122.4(4) ?
N1 C1 C11A . . 111.2(12) ?
C2 C1 C11A . . 124.1(12) ?
N1 C1 Se1 . . 122.0(3) ?
C2 C1 Se1 . . 115.6(3) ?
C1 Se1 C11 . . 102.5(3) ?
C1 C11A Se1A . . 108.9(16) ?
C1 C11A H11C . . 109.9 ?
Se1A C11A H11C . . 109.9 ?
C1 C11A H11D . . 109.9 ?
Se1A C11A H11D . . 109.9 ?
H11C C11A H11D . . 108.3 ?
C3 C2 C1 . . 119.5(4) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
C2 C3 C4 . . 118.8(4) ?
C2 C3 H3 . . 120.6 ?
C4 C3 H3 . . 120.6 ?
C5 C4 C3 . . 118.5(4) ?
C5 C4 H4 . . 120.8 ?
C3 C4 H4 . . 120.8 ?
N1 C5 C4 . . 123.7(4) ?
N1 C5 H5 . . 118.2 ?
C4 C5 H5 . . 118.2 ?
C6 N2 C10 . . 118.0(3) ?
C6 N2 Cu1 . . 120.4(2) ?
C10 N2 Cu1 . . 121.6(2) ?
N2 C6 C7 . . 121.7(3) ?
N2 C6 C11 . . 114.9(4) ?
C7 C6 C11 . . 123.3(4) ?
N2 C6 Se1A . . 121.7(3) ?
C7 C6 Se1A . . 115.8(3) ?
C11A Se1A C6 . . 96.9(10) ?
C6 C11 Se1 . . 111.8(5) ?
C6 C11 H11A . . 109.3 ?
Se1 C11 H11A . . 109.3 ?
C6 C11 H11B . . 109.3 ?
Se1 C11 H11B . . 109.3 ?
H11A C11 H11B . . 107.9 ?
C8 C7 C6 . . 119.5(4) ?
C8 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C9 C8 C7 . . 119.0(4) ?
C9 C8 H8 . . 120.5 ?
C7 C8 H8 . . 120.5 ?
C8 C9 C10 . . 118.9(4) ?
C8 C9 H9 . . 120.5 ?
C10 C9 H9 . . 120.5 ?
N2 C10 C9 . . 122.8(4) ?
N2 C10 H10 . . 118.6 ?
C9 C10 H10 . . 118.6 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . -0.9(6) ?
Cu1 N1 C1 C2 . . . . 175.7(3) ?
C5 N1 C1 C11A . . . . -164.2(14) ?
Cu1 N1 C1 C11A . . . . 12.4(14) ?
C5 N1 C1 Se1 . . . . 178.1(3) ?
Cu1 N1 C1 Se1 . . . . -5.3(4) ?
N1 C1 C11A Se1A . . . . -78.3(17) ?
C2 C1 C11A Se1A . . . . 118.7(13) ?
N1 C1 C2 C3 . . . . -1.3(7) ?
C11A C1 C2 C3 . . . . 159.9(16) ?
Se1 C1 C2 C3 . . . . 179.7(4) ?
C1 C2 C3 C4 . . . . 2.7(8) ?
C2 C3 C4 C5 . . . . -2.0(8) ?
C1 N1 C5 C4 . . . . 1.7(6) ?
Cu1 N1 C5 C4 . . . . -175.4(3) ?
C3 C4 C5 N1 . . . . -0.2(7) ?
C10 N2 C6 C7 . . . . -1.1(5) ?
Cu1 N2 C6 C7 . . . . 175.8(3) ?
C10 N2 C6 C11 . . . . -178.6(4) ?
Cu1 N2 C6 C11 . . . . -1.6(5) ?
C10 N2 C6 Se1A . . . . 168.0(3) ?
Cu1 N2 C6 Se1A . . . . -15.1(4) ?
N2 C6 C11 Se1 . . . . -83.0(5) ?
C7 C6 C11 Se1 . . . . 99.6(5) ?
N2 C6 C7 C8 . . . . 0.9(5) ?
C11 C6 C7 C8 . . . . 178.2(5) ?
Se1A C6 C7 C8 . . . . -168.8(4) ?
C6 C7 C8 C9 . . . . -0.1(6) ?
C7 C8 C9 C10 . . . . -0.4(6) ?
C6 N2 C10 C9 . . . . 0.6(5) ?
Cu1 N2 C10 C9 . . . . -176.3(3) ?
C8 C9 C10 N2 . . . . 0.1(6) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C11 H11A I1 1_565 0.97 3.11 4.043(7) 161.0 ?
C11 H11B I1 2_665 0.97 3.29 4.182(7) 153.6 ?
C9 H9 I1 2_565 0.93 3.21 4.023(4) 146.9 ?
C10 H10 I1 . 0.93 3.25 3.877(4) 127.0 ?



####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1844935'
_audit_update_record             
;
2018-08-27 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          443.15-445.15
_chemical_formula_moiety         
;
0.27(C20 H16 Cl2 Cu2 N4 S2 Se2, 0.73(C20 H16 Cl2 Cu2 N4 Se4)
;
_chemical_formula_sum            'C20 H16 Cl2 Cu2 N4 S0.55 Se3.45'
_chemical_formula_weight         800.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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'
N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.0998 0.0984 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3240 0.8257 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se 0.2367 1.4831 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.0826 0.0763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.0642(3)
_cell_length_b                   8.6710(3)
_cell_length_c                   9.5068(3)
_cell_angle_alpha                82.4090(10)
_cell_angle_beta                 73.8920(10)
_cell_angle_gamma                67.8180(10)
_cell_volume                     591.11(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      23.59

_exptl_crystal_description       Block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.248
_exptl_crystal_F_000             382
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.099
_exptl_absorpt_coefficient_mu    3.905
_shelx_estimated_absorpt_T_min   0.619
_shelx_estimated_absorpt_T_max   0.698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6496
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_process_details   
;
        SADABS(Bruker, 2007) was used to perform the data scaling
        and semi-empirical absorption correction based on symmetry-
        related refkections.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.56086
_diffrn_radiation_type           AgK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29331
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.400
_diffrn_reflns_theta_max         23.640
_diffrn_reflns_theta_full        19.665
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3624
_reflns_number_gt                3323
_reflns_threshold_expression     'I > 2σ(I)'

_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       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2016)'
_computing_structure_solution    'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  vim
_refine_special_details          
;Two large peaks of approximately 4 e Å⁻³were observed close to the the 
selenium atoms. After considerable testing, the only chemical and 
crystallographic solution was to consider disorder with a selenosulfide 
species together with the diselenide. This was modeled and produced a 27%
occupancy with the selenosulfide over two orientations and 73% diselenide.
The possibilty of a disufide was not considered due to the very small
percentage (~9%).,Two large peaks of approximately 4 e Å⁻³were observed close to the the  selenium atoms. After considerable testing, the only chemical and  crystallographic solution was to consider disorder with a selenosulfide  species together with the diselenide. This was modeled and produced a 27% occupancy with the selenosulfide over two orientations and 73% diselenide. The possibilty of a disufide was not considered due to the very small percentage (~9%).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0109P)²+1.1193P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3624
_refine_ls_number_parameters     166
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0512
_refine_ls_wR_factor_gt          0.0502
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_restrained_S_all      1.184
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.098

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
Se1 Se 0.24062(4) 0.35412(6) 0.89794(4) 0.01375(10) Uani 0.727(4) 1 d . . P A 1
Se2 Se 0.29879(12) 0.56598(10) 0.74136(9) 0.01313(12) Uani 0.727(4) 1 d . . P A
1
Se1' Se 0.24062(4) 0.35412(6) 0.89794(4) 0.01375(10) Uani 0.148(3) 1 d . . P A
2
S1 S 0.3071(19) 0.5442(15) 0.7601(13) 0.0109(19) Uani 0.148(3) 1 d . U P A 2
Se2' Se 0.29879(12) 0.56598(10) 0.74136(9) 0.01313(12) Uani 0.125(3) 1 d . . P
A 3
S2 S 0.2532(7) 0.4001(8) 0.8642(7) 0.0080(11) Uani 0.125(3) 1 d . U P A 3
Cu1 Cu 0.45732(4) 0.15286(3) 0.60067(3) 0.01405(7) Uani 1 1 d . . . . .
Cl1 Cl 0.28737(7) -0.02388(6) 0.61378(5) 0.01274(10) Uani 1 1 d . . . . .
N1 N 0.5810(2) 0.1194(2) 0.76156(19) 0.0115(3) Uani 1 1 d . . . . .
C1 C 0.7542(3) 0.0096(3) 0.7547(2) 0.0135(4) Uani 1 1 d . . . . .
H1 H 0.822617 -0.047707 0.666386 0.016 Uiso 1 1 calc R U . . .
N2 N 0.3154(2) 0.3714(2) 0.51287(19) 0.0114(3) Uani 1 1 d . . . . .
C2 C 0.8367(3) -0.0235(3) 0.8711(3) 0.0165(4) Uani 1 1 d . . . . .
H2 H 0.957748 -0.103797 0.863007 0.020 Uiso 1 1 calc R U . . .
C3 C 0.7400(3) 0.0624(3) 0.9993(3) 0.0195(4) Uani 1 1 d . . . . .
H3 H 0.792851 0.040867 1.080803 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5643(3) 0.1805(3) 1.0062(2) 0.0176(4) Uani 1 1 d . . . . .
H4 H 0.496365 0.243901 1.091458 0.021 Uiso 1 1 calc R U . . .
C5 C 0.4896(3) 0.2042(3) 0.8859(2) 0.0141(4) Uani 1 1 d . . . . .
C6 C 0.2572(3) 0.5250(3) 0.5625(2) 0.0117(4) Uani 1 1 d . . . . .
C7 C 0.1633(3) 0.6679(3) 0.4886(2) 0.0147(4) Uani 1 1 d . . . . .
H7 H 0.127160 0.775361 0.525780 0.018 Uiso 1 1 calc R U . . .
C10 C 0.2767(3) 0.3562(3) 0.3873(2) 0.0132(4) Uani 1 1 d . . . . .
H10 H 0.316442 0.247663 0.351193 0.016 Uiso 1 1 calc R U . . .
C9 C 0.1820(3) 0.4903(3) 0.3083(2) 0.0149(4) Uani 1 1 d . . . . .
H9 H 0.157023 0.473823 0.220631 0.018 Uiso 1 1 calc R U . . .
C8 C 0.1242(3) 0.6496(3) 0.3600(3) 0.0165(4) Uani 1 1 d . . . . .
H8 H 0.059068 0.744208 0.308149 0.020 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
Se1 C5 1.917(2) . ?
Se1 Se2 2.3134(10) . ?
Se2 C6 1.922(2) . ?
Se1' C5 1.917(2) . ?
Se1' S1 2.104(12) . ?
S1 C6 2.067(13) . ?
Se2' S2 1.812(8) . ?
Se2' C6 1.922(2) . ?
S2 C5 2.060(6) . ?
Cu1 N1 1.9823(18) . ?
Cu1 N2 2.0180(18) . ?
Cu1 Cl1 2.3839(6) . ?
Cu1 Cl1 2.4861(6) 2_656 ?
N1 C5 1.348(3) . ?
N1 C1 1.350(3) . ?
C1 C2 1.390(3) . ?
C1 H1 0.9500 . ?
N2 C6 1.337(3) . ?
N2 C10 1.349(3) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C6 C7 1.400(3) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C10 C9 1.384(3) . ?
C10 H10 0.9500 . ?
C9 C8 1.390(3) . ?
C9 H9 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
C5 Se1 Se2 99.47(7) . . ?
C6 Se2 Se1 102.99(7) . . ?
C5 Se1' S1 96.8(4) . . ?
C6 S1 Se1' 105.7(6) . . ?
S2 Se2' C6 103.06(18) . . ?
Se2' S2 C5 113.3(3) . . ?
N1 Cu1 N2 127.42(7) . . ?
N1 Cu1 Cl1 115.31(5) . . ?
N2 Cu1 Cl1 105.44(5) . . ?
N1 Cu1 Cl1 104.39(5) . 2_656 ?
N2 Cu1 Cl1 101.89(5) . 2_656 ?
Cl1 Cu1 Cl1 97.113(18) . 2_656 ?
Cu1 Cl1 Cu1 82.887(18) . 2_656 ?
C5 N1 C1 117.40(18) . . ?
C5 N1 Cu1 119.94(14) . . ?
C1 N1 Cu1 122.62(15) . . ?
N1 C1 C2 122.9(2) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C6 N2 C10 117.40(18) . . ?
C6 N2 Cu1 128.69(15) . . ?
C10 N2 Cu1 113.92(14) . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 118.8(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 123.1(2) . . ?
N1 C5 Se1' 117.29(16) . . ?
C4 C5 Se1' 119.56(17) . . ?
N1 C5 Se1 117.29(16) . . ?
C4 C5 Se1 119.56(17) . . ?
N1 C5 S2 112.7(2) . . ?
C4 C5 S2 123.3(2) . . ?
N2 C6 C7 123.02(19) . . ?
N2 C6 Se2 122.14(16) . . ?
C7 C6 Se2 114.84(15) . . ?
N2 C6 Se2' 122.14(16) . . ?
C7 C6 Se2' 114.84(15) . . ?
N2 C6 S1 116.7(4) . . ?
C7 C6 S1 120.3(4) . . ?
C8 C7 C6 118.70(19) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
N2 C10 C9 123.5(2) . . ?
N2 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
C10 C9 C8 118.6(2) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C7 C8 C9 118.7(2) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?

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
C6 Se2' S2 C5 100.0(2) . . . . ?
C5 N1 C1 C2 2.7(3) . . . . ?
Cu1 N1 C1 C2 -175.13(16) . . . . ?
N1 C1 C2 C3 -1.6(3) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 2.1(3) . . . . ?
C1 N1 C5 C4 -1.4(3) . . . . ?
Cu1 N1 C5 C4 176.53(17) . . . . ?
C1 N1 C5 Se1' -177.82(15) . . . . ?
Cu1 N1 C5 Se1' 0.1(2) . . . . ?
C1 N1 C5 Se1 -177.82(15) . . . . ?
Cu1 N1 C5 Se1 0.1(2) . . . . ?
C1 N1 C5 S2 167.7(3) . . . . ?
Cu1 N1 C5 S2 -14.4(3) . . . . ?
C3 C4 C5 N1 -1.0(3) . . . . ?
C3 C4 C5 Se1' 175.35(17) . . . . ?
C3 C4 C5 Se1 175.35(17) . . . . ?
C3 C4 C5 S2 -169.0(3) . . . . ?
C10 N2 C6 C7 -1.6(3) . . . . ?
Cu1 N2 C6 C7 178.31(15) . . . . ?
C10 N2 C6 Se2 179.04(15) . . . . ?
Cu1 N2 C6 Se2 -1.1(3) . . . . ?
C10 N2 C6 Se2' 179.04(15) . . . . ?
Cu1 N2 C6 Se2' -1.1(3) . . . . ?
C10 N2 C6 S1 177.1(5) . . . . ?
Cu1 N2 C6 S1 -3.0(5) . . . . ?
N2 C6 C7 C8 1.8(3) . . . . ?
Se2 C6 C7 C8 -178.74(16) . . . . ?
Se2' C6 C7 C8 -178.74(16) . . . . ?
S1 C6 C7 C8 -176.8(5) . . . . ?
C6 N2 C10 C9 0.5(3) . . . . ?
Cu1 N2 C10 C9 -179.43(17) . . . . ?
N2 C10 C9 C8 0.4(3) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C10 C9 C8 C7 -0.1(3) . . . . ?




_exptl_crystal_recrystallization_method 'mother liquor'
