#------------------------------------------------------------------------------
#$Date: 2025-03-07 18:30:27 +0200 (Fri, 07 Mar 2025) $
#$Revision: 298328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/45/7244590.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7244590
loop_
_publ_author_name
'Parisi, Emmanuele'
'CARELLA, Antonio'
'Borbone, Fabio'
'Gentile, Francesco Silvio'
'Centore, Roberto'
'Chiarella, Fabio'
_publ_section_title
;
 Effect of chalcogen bond on the packing and coordination geometry in
 hybrid organic-inorganic Cu(II) networks.
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00069E
_journal_year                    2022
_chemical_formula_moiety         'C12 H8 Br2 Cu N4 Se2'
_chemical_formula_sum            'C12 H8 Br2 Cu N4 Se2'
_chemical_formula_weight         589.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-10 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                94.514(10)
_cell_angle_beta                 109.679(9)
_cell_angle_gamma                102.793(11)
_cell_formula_units_Z            2
_cell_length_a                   8.4870(10)
_cell_length_b                   9.5870(12)
_cell_length_c                   10.3190(8)
_cell_measurement_reflns_used    277
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.365
_cell_measurement_theta_min      2.897
_cell_volume                     760.13(16)
_computing_cell_refinement
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_collection       'Collect (Nonius, 1999)'
_computing_data_reduction
;
EvalCCD (Duisenberg et al., 2003)
;
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 2012) and 
Mercury (Macrae et al., 2006)
;
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution
;
SIR97 (Altomare et al., 1999)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method
;
CCD rotation images, thick slices
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9198
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         3.283
_diffrn_source                   'normal-focus sealed tube'
_exptl_absorpt_coefficient_mu    11.477
_exptl_absorpt_correction_T_max  0.369
_exptl_absorpt_correction_T_min  0.135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Bruker, 2001)
;
_exptl_crystal_colour            'DARK BROWN'
_exptl_crystal_density_diffrn    2.576
_exptl_crystal_description       LOZENGE
_exptl_crystal_F_000             550
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.924
_refine_diff_density_min         -1.149
_refine_diff_density_rms         0.231
_refine_ls_extinction_coef       0.0060(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0454P)²+10.9147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1435
_refine_ls_wR_factor_ref         0.1529
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2634
_reflns_number_total             3438
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00069e2.cif
_cod_data_source_block           shelx_CCDC3
_cod_depositor_comments
;

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         294.75
_cod_original_formula_moiety         'C6 H4 Br Cu0.50 N2 Se'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        760.13(15)
_cod_original_formula_sum        'C6 H4 Br Cu0.50 N2 Se'
_cod_database_code               7244590
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.108
_shelx_estimated_absorpt_t_max   0.393
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8129(12) 0.2981(10) 0.3721(9) 0.0250(18) Uani 1 1 d . . . . .
C2 C 0.8531(16) 0.1692(11) 0.4163(11) 0.039(2) Uani 1 1 d . . . . .
H2 H 0.854582 0.149015 0.503364 0.046 Uiso 1 1 calc R U . . .
C3 C 0.8887(18) 0.0772(12) 0.3329(12) 0.045(3) Uani 1 1 d . . . . .
H3 H 0.911583 -0.008182 0.361612 0.054 Uiso 1 1 calc R U . . .
C4 C 0.8924(14) 0.1078(12) 0.1986(11) 0.037(2) Uani 1 1 d . . . . .
H4 H 0.922500 0.043908 0.144415 0.044 Uiso 1 1 calc R U . . .
C5 C 0.8531(14) 0.2270(10) 0.1508(10) 0.032(2) Uani 1 1 d . . . . .
H5 H 0.853971 0.244407 0.063575 0.038 Uiso 1 1 calc R U . . .
C6 C 0.8106(11) 0.3251(9) 0.2338(8) 0.0211(16) Uani 1 1 d . . . . .
C7 C 0.6814(13) 0.7350(10) -0.3403(9) 0.0266(19) Uani 1 1 d . . . . .
C8 C 0.6523(15) 0.8598(11) -0.4016(10) 0.036(2) Uani 1 1 d . . . . .
H8 H 0.646835 0.864155 -0.492673 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6330(15) 0.9715(11) -0.3255(11) 0.039(2) Uani 1 1 d . . . . .
H9 H 0.617366 1.054286 -0.363800 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6361(17) 0.9643(12) -0.1883(12) 0.042(3) Uani 1 1 d . . . . .
H10 H 0.617478 1.041315 -0.139973 0.050 Uiso 1 1 calc R U . . .
C11 C 0.6653(14) 0.8487(10) -0.1247(10) 0.031(2) Uani 1 1 d . . . . .
H11 H 0.669331 0.847571 -0.033634 0.038 Uiso 1 1 calc R U . . .
C12 C 0.6894(12) 0.7306(9) -0.1990(9) 0.0225(17) Uani 1 1 d . . . . .
N1 N 0.7796(11) 0.3965(9) 0.4474(8) 0.0286(17) Uani 1 1 d . . . . .
N2 N 0.7683(11) 0.4487(8) 0.2018(8) 0.0281(17) Uani 1 1 d . . . . .
N3 N 0.7161(11) 0.6069(8) -0.1544(7) 0.0247(16) Uani 1 1 d . . . . .
N4 N 0.7033(12) 0.6214(9) -0.4057(8) 0.0327(18) Uani 1 1 d . . . . .
Se1 Se 0.73695(14) 0.53779(10) 0.34886(9) 0.0282(3) Uani 1 1 d . . . . .
Se2 Se 0.73521(14) 0.49259(10) -0.29202(9) 0.0293(3) Uani 1 1 d . . . . .
Br2 Br 0.99081(14) 0.73152(11) 0.15019(10) 0.0346(3) Uani 1 1 d . . . . .
Br1 Br 0.50844(13) 0.31874(9) -0.10373(9) 0.0294(3) Uani 1 1 d . . . . .
Cu1 Cu 0.73700(15) 0.53676(11) 0.02838(10) 0.0243(3) Uani 1 1 d . . . . .
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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 124.5(8) . . ?
N1 C1 C6 117.2(8) . . ?
C2 C1 C6 118.2(8) . . ?
C3 C2 C1 120.0(9) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 121.2(9) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 121.2(10) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.4(9) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
N2 C6 C5 126.9(8) . . ?
N2 C6 C1 113.2(8) . . ?
C5 C6 C1 119.9(8) . . ?
N4 C7 C8 123.5(8) . . ?
N4 C7 C12 117.0(8) . . ?
C8 C7 C12 119.5(8) . . ?
C9 C8 C7 119.1(9) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 120.9(9) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 122.2(10) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 118.9(9) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
N3 C12 C11 127.2(8) . . ?
N3 C12 C7 113.5(7) . . ?
C11 C12 C7 119.3(8) . . ?
C1 N1 Se1 108.4(6) . . ?
C6 N2 Se1 108.6(6) . . ?
C6 N2 Cu1 131.0(6) . . ?
Se1 N2 Cu1 120.4(4) . . ?
C12 N3 Se2 108.6(6) . . ?
C12 N3 Cu1 132.1(6) . . ?
Se2 N3 Cu1 119.3(4) . . ?
C7 N4 Se2 108.6(6) . . ?
N1 Se1 N2 92.5(3) . . ?
N4 Se2 N3 92.3(3) . . ?
N2 Cu1 N3 173.3(3) . . ?
N2 Cu1 Br2 90.6(2) . . ?
N3 Cu1 Br2 91.1(2) . . ?
N2 Cu1 Br1 89.2(2) . . ?
N3 Cu1 Br1 88.1(2) . . ?
Br2 Cu1 Br1 171.21(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.313(12) . ?
C1 C2 1.422(13) . ?
C1 C6 1.464(11) . ?
C2 C3 1.336(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.448(16) . ?
C3 H3 0.9300 . ?
C4 C5 1.344(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.408(12) . ?
C5 H5 0.9300 . ?
C6 N2 1.346(11) . ?
C7 N4 1.317(12) . ?
C7 C8 1.427(12) . ?
C7 C12 1.442(12) . ?
C8 C9 1.350(15) . ?
C8 H8 0.9300 . ?
C9 C10 1.414(16) . ?
C9 H9 0.9300 . ?
C10 C11 1.360(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.408(12) . ?
C11 H11 0.9300 . ?
C12 N3 1.342(11) . ?
N1 Se1 1.785(7) . ?
N2 Se1 1.808(7) . ?
N2 Cu1 2.001(7) . ?
N3 Se2 1.798(7) . ?
N3 Cu1 2.017(7) . ?
N4 Se2 1.771(8) . ?
Br2 Cu1 2.3942(16) . ?
Br1 Cu1 2.4423(15) . ?
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
N1 C1 C2 C3 -178.6(11) . . . . ?
C6 C1 C2 C3 0.5(16) . . . . ?
C1 C2 C3 C4 1.8(19) . . . . ?
C2 C3 C4 C5 -2.8(19) . . . . ?
C3 C4 C5 C6 1.2(17) . . . . ?
C4 C5 C6 N2 -180.0(10) . . . . ?
C4 C5 C6 C1 1.2(15) . . . . ?
N1 C1 C6 N2 -1.9(12) . . . . ?
C2 C1 C6 N2 178.9(9) . . . . ?
N1 C1 C6 C5 177.1(9) . . . . ?
C2 C1 C6 C5 -2.1(14) . . . . ?
N4 C7 C8 C9 -179.4(11) . . . . ?
C12 C7 C8 C9 0.0(16) . . . . ?
C7 C8 C9 C10 -1.9(17) . . . . ?
C8 C9 C10 C11 2.7(19) . . . . ?
C9 C10 C11 C12 -1.5(18) . . . . ?
C10 C11 C12 N3 -178.6(11) . . . . ?
C10 C11 C12 C7 -0.4(15) . . . . ?
N4 C7 C12 N3 -1.0(13) . . . . ?
C8 C7 C12 N3 179.6(9) . . . . ?
N4 C7 C12 C11 -179.4(9) . . . . ?
C8 C7 C12 C11 1.1(14) . . . . ?
C2 C1 N1 Se1 180.0(9) . . . . ?
C6 C1 N1 Se1 0.8(10) . . . . ?
C5 C6 N2 Se1 -177.0(8) . . . . ?
C1 C6 N2 Se1 1.9(10) . . . . ?
C5 C6 N2 Cu1 3.4(15) . . . . ?
C1 C6 N2 Cu1 -177.7(7) . . . . ?
C11 C12 N3 Se2 179.2(8) . . . . ?
C7 C12 N3 Se2 0.9(10) . . . . ?
C11 C12 N3 Cu1 -1.1(15) . . . . ?
C7 C12 N3 Cu1 -179.4(7) . . . . ?
C8 C7 N4 Se2 180.0(9) . . . . ?
C12 C7 N4 Se2 0.6(11) . . . . ?
C1 N1 Se1 N2 0.2(7) . . . . ?
C6 N2 Se1 N1 -1.2(7) . . . . ?
Cu1 N2 Se1 N1 178.4(5) . . . . ?
C7 N4 Se2 N3 0.0(7) . . . . ?
C12 N3 Se2 N4 -0.5(7) . . . . ?
Cu1 N3 Se2 N4 179.7(5) . . . . ?
