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#$Date: 2023-09-04 17:14:14 +0300 (Mon, 04 Sep 2023) $
#$Revision: 285988 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/97/1569771.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_1569771
loop_
_publ_author_name
'Aliyeva, Vusala A.'
'Gurbanov, Atash V.'
'Mahmoud, Abdallah G.'
'Gomila, Rosa M.'
'Frontera, Antonio'
'Mahmudov, Kamran T.'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Chalcogen bonding in copper(II)-mediated synthesis.
;
_journal_issue                   0
_journal_name_full               'Faraday discussions'
_journal_page_first              77
_journal_page_last               95
_journal_paper_doi               10.1039/d2fd00160h
_journal_volume                  244
_journal_year                    2023
_chemical_formula_moiety         'C24 H22 Cl2 Cu N2 Se2'
_chemical_formula_sum            'C24 H22 Cl2 Cu N2 Se2'
_chemical_formula_weight         630.79
_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-2019/1
_audit_update_record
;
2022-10-22 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                77.9040(10)
_cell_angle_beta                 73.2640(10)
_cell_angle_gamma                73.8940(10)
_cell_formula_units_Z            2
_cell_length_a                   9.5330(3)
_cell_length_b                   10.8335(3)
_cell_length_c                   12.5170(4)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.43
_cell_volume                     1177.49(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            92063
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.529
_diffrn_reflns_theta_min         1.976
_exptl_absorpt_coefficient_mu    4.261
_exptl_absorpt_correction_T_max  0.746070
_exptl_absorpt_correction_T_min  0.561702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
TWINABS 2012/1: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.
(2015). J. Appl. Cryst. 48 3-10.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_description       plate
_exptl_crystal_F_000             622
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.150
_refine_diff_density_max         1.725
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         7191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.215
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0004P)²+5.4969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6457
_reflns_number_total             7191
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2fd00160h9.cif
_cod_data_source_block           AO3
_cod_database_code               1569771
_shelx_shelxl_version_number     2019/1
_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.
;
_shelx_estimated_absorpt_t_min   0.382
_shelx_estimated_absorpt_t_max   0.567
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
Cu1 Cu 0.500000 0.000000 0.500000 0.01589(11) Uani 1 2 d S . P . .
Cu2 Cu 0.000000 0.500000 1.000000 0.01587(11) Uani 1 2 d S . P . .
Cl1 Cl 0.34222(10) 0.19880(8) 0.53057(7) 0.02115(16) Uani 1 1 d . . . . .
Cl2 Cl -0.14691(10) 0.35636(9) 1.02582(7) 0.02116(16) Uani 1 1 d . . . . .
Se1 Se 0.75667(4) 0.13065(4) 0.41899(3) 0.01971(8) Uani 1 1 d . . . . .
Se2 Se 0.26152(4) 0.29676(4) 0.90408(3) 0.02100(8) Uani 1 1 d . . . . .
N1 N 0.5097(3) 0.0503(3) 0.3326(2) 0.0175(5) Uani 1 1 d . . . . .
N2 N 0.0008(3) 0.5408(3) 0.8335(2) 0.0168(5) Uani 1 1 d . . . . .
C1 C 0.9143(4) 0.0207(3) 0.3239(3) 0.0189(6) Uani 1 1 d . . . . .
C2 C 0.9980(5) -0.0882(4) 0.3773(4) 0.0303(9) Uani 1 1 d . . . . .
H2A H 0.976014 -0.104973 0.457270 0.036 Uiso 1 1 calc R U . . .
C3 C 1.1127(5) -0.1718(4) 0.3142(5) 0.0373(10) Uani 1 1 d . . . . .
H3A H 1.169987 -0.245831 0.351171 0.045 Uiso 1 1 calc R U . . .
C4 C 1.1459(5) -0.1494(4) 0.1976(5) 0.0358(10) Uani 1 1 d . . . . .
H4A H 1.223158 -0.209052 0.154635 0.043 Uiso 1 1 calc R U . . .
C5 C 1.0649(5) -0.0388(5) 0.1441(4) 0.0322(9) Uani 1 1 d . . . . .
H5A H 1.088641 -0.021739 0.064151 0.039 Uiso 1 1 calc R U . . .
C6 C 0.9497(4) 0.0468(4) 0.2065(3) 0.0267(8) Uani 1 1 d . . . . .
H6A H 0.895214 0.122784 0.169601 0.032 Uiso 1 1 calc R U . . .
C7 C 0.6367(4) 0.2270(3) 0.3133(3) 0.0192(6) Uani 1 1 d . . . . .
H7A H 0.554001 0.293246 0.351653 0.023 Uiso 1 1 calc R U . . .
H7B H 0.700850 0.273410 0.249927 0.023 Uiso 1 1 calc R U . . .
C8 C 0.5695(4) 0.1472(3) 0.2659(3) 0.0170(6) Uani 1 1 d . . . . .
C9 C 0.5667(4) 0.1778(4) 0.1527(3) 0.0230(7) Uani 1 1 d . . . . .
H9A H 0.611973 0.244569 0.105945 0.028 Uiso 1 1 calc R U . . .
C10 C 0.4971(5) 0.1101(4) 0.1082(3) 0.0274(8) Uani 1 1 d . . . . .
H10A H 0.493516 0.130650 0.031284 0.033 Uiso 1 1 calc R U . . .
C11 C 0.4334(5) 0.0125(4) 0.1778(3) 0.0266(8) Uani 1 1 d . . . . .
H11A H 0.383883 -0.034308 0.150061 0.032 Uiso 1 1 calc R U . . .
C12 C 0.4434(4) -0.0155(4) 0.2888(3) 0.0221(7) Uani 1 1 d . . . . .
H12A H 0.401762 -0.083992 0.336171 0.026 Uiso 1 1 calc R U . . .
C13 C 0.4192(4) 0.3782(4) 0.8115(3) 0.0210(7) Uani 1 1 d . . . . .
C14 C 0.4959(4) 0.4270(4) 0.8664(4) 0.0263(8) Uani 1 1 d . . . . .
H14A H 0.467583 0.421348 0.946179 0.032 Uiso 1 1 calc R U . . .
C15 C 0.6139(5) 0.4838(4) 0.8041(4) 0.0303(9) Uani 1 1 d . . . . .
H15A H 0.667532 0.515531 0.841506 0.036 Uiso 1 1 calc R U . . .
C16 C 0.6537(5) 0.4945(4) 0.6873(4) 0.0312(9) Uani 1 1 d . . . . .
H16A H 0.733118 0.534844 0.644662 0.037 Uiso 1 1 calc R U . . .
C17 C 0.5764(4) 0.4458(4) 0.6332(4) 0.0278(8) Uani 1 1 d . . . . .
H17A H 0.603256 0.453344 0.553276 0.033 Uiso 1 1 calc R U . . .
C18 C 0.4606(4) 0.3862(4) 0.6945(3) 0.0233(7) Uani 1 1 d . . . . .
H18A H 0.409929 0.351212 0.657130 0.028 Uiso 1 1 calc R U . . .
C19 C 0.1381(4) 0.3181(4) 0.7986(3) 0.0203(7) Uani 1 1 d . . . . .
H19A H 0.200923 0.275740 0.732190 0.024 Uiso 1 1 calc R U . . .
H19B H 0.056029 0.272402 0.835107 0.024 Uiso 1 1 calc R U . . .
C20 C 0.0698(4) 0.4567(4) 0.7587(3) 0.0185(6) Uani 1 1 d . . . . .
C21 C 0.0735(4) 0.4943(4) 0.6443(3) 0.0234(7) Uani 1 1 d . . . . .
H21A H 0.126691 0.435114 0.591869 0.028 Uiso 1 1 calc R U . . .
C22 C -0.0008(5) 0.6186(4) 0.6076(3) 0.0273(8) Uani 1 1 d . . . . .
H22A H -0.000519 0.644890 0.530233 0.033 Uiso 1 1 calc R U . . .
C23 C -0.0747(4) 0.7032(4) 0.6847(3) 0.0252(7) Uani 1 1 d . . . . .
H23A H -0.128276 0.788146 0.661981 0.030 Uiso 1 1 calc R U . . .
C24 C -0.0696(4) 0.6620(4) 0.7965(3) 0.0217(7) Uani 1 1 d . . . . .
H24A H -0.117679 0.721518 0.849210 0.026 Uiso 1 1 calc R U . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 180.0 2_656 . ?
N1 Cu1 Cl1 90.93(9) 2_656 . ?
N1 Cu1 Cl1 89.07(9) . . ?
N1 Cu1 Cl1 89.07(9) 2_656 2_656 ?
N1 Cu1 Cl1 90.93(9) . 2_656 ?
Cl1 Cu1 Cl1 180.0 . 2_656 ?
N2 Cu2 N2 180.0 2_567 . ?
N2 Cu2 Cl2 89.94(9) 2_567 2_567 ?
N2 Cu2 Cl2 90.06(9) . 2_567 ?
N2 Cu2 Cl2 90.06(9) 2_567 . ?
N2 Cu2 Cl2 89.94(9) . . ?
Cl2 Cu2 Cl2 180.0 2_567 . ?
C1 Se1 C7 100.59(15) . . ?
C13 Se2 C19 100.89(15) . . ?
C8 N1 C12 119.0(3) . . ?
C8 N1 Cu1 124.9(2) . . ?
C12 N1 Cu1 116.1(2) . . ?
C20 N2 C24 118.6(3) . . ?
C20 N2 Cu2 124.4(2) . . ?
C24 N2 Cu2 117.0(2) . . ?
C2 C1 C6 119.9(4) . . ?
C2 C1 Se1 116.7(3) . . ?
C6 C1 Se1 123.4(3) . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C6 C5 C4 120.5(4) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 H6A 120.2 . . ?
C1 C6 H6A 120.2 . . ?
C8 C7 Se1 115.5(2) . . ?
C8 C7 H7A 108.4 . . ?
Se1 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
Se1 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
N1 C8 C9 121.0(3) . . ?
N1 C8 C7 120.4(3) . . ?
C9 C8 C7 118.6(3) . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C11 C10 C9 118.9(3) . . ?
C11 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
C10 C11 C12 118.6(4) . . ?
C10 C11 H11A 120.7 . . ?
C12 C11 H11A 120.7 . . ?
N1 C12 C11 122.8(3) . . ?
N1 C12 H12A 118.6 . . ?
C11 C12 H12A 118.6 . . ?
C18 C13 C14 120.2(4) . . ?
C18 C13 Se2 122.6(3) . . ?
C14 C13 Se2 117.2(3) . . ?
C15 C14 C13 119.8(4) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C14 C15 C16 120.3(4) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C17 119.5(4) . . ?
C15 C16 H16A 120.2 . . ?
C17 C16 H16A 120.2 . . ?
C18 C17 C16 120.8(4) . . ?
C18 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?
C17 C18 C13 119.4(4) . . ?
C17 C18 H18A 120.3 . . ?
C13 C18 H18A 120.3 . . ?
C20 C19 Se2 114.6(2) . . ?
C20 C19 H19A 108.6 . . ?
Se2 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
Se2 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
N2 C20 C21 121.1(3) . . ?
N2 C20 C19 119.9(3) . . ?
C21 C20 C19 118.9(3) . . ?
C22 C21 C20 119.6(4) . . ?
C22 C21 H21A 120.2 . . ?
C20 C21 H21A 120.2 . . ?
C23 C22 C21 119.1(3) . . ?
C23 C22 H22A 120.5 . . ?
C21 C22 H22A 120.5 . . ?
C22 C23 C24 118.7(4) . . ?
C22 C23 H23A 120.7 . . ?
C24 C23 H23A 120.7 . . ?
N2 C24 C23 122.8(4) . . ?
N2 C24 H24A 118.6 . . ?
C23 C24 H24A 118.6 . . ?
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
Cu1 N1 2.033(3) 2_656 ?
Cu1 N1 2.033(3) . ?
Cu1 Cl1 2.2943(8) . ?
Cu1 Cl1 2.2943(8) 2_656 ?
Cu2 N2 2.036(3) 2_567 ?
Cu2 N2 2.036(3) . ?
Cu2 Cl2 2.2858(9) 2_567 ?
Cu2 Cl2 2.2858(9) . ?
Se1 C1 1.914(4) . ?
Se1 C7 1.944(3) . ?
Se2 C13 1.920(4) . ?
Se2 C19 1.949(4) . ?
N1 C8 1.347(4) . ?
N1 C12 1.350(5) . ?
N2 C20 1.345(4) . ?
N2 C24 1.351(5) . ?
C1 C2 1.390(5) . ?
C1 C6 1.394(5) . ?
C2 C3 1.375(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.386(7) . ?
C3 H3A 0.9500 . ?
C4 C5 1.388(7) . ?
C4 H4A 0.9500 . ?
C5 C6 1.386(6) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.500(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.392(5) . ?
C9 C10 1.393(6) . ?
C9 H9A 0.9500 . ?
C10 C11 1.382(6) . ?
C10 H10A 0.9500 . ?
C11 C12 1.383(5) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C18 1.393(5) . ?
C13 C14 1.392(5) . ?
C14 C15 1.390(6) . ?
C14 H14A 0.9500 . ?
C15 C16 1.388(7) . ?
C15 H15A 0.9500 . ?
C16 C17 1.390(6) . ?
C16 H16A 0.9500 . ?
C17 C18 1.387(6) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C20 1.503(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.398(5) . ?
C21 C22 1.387(6) . ?
C21 H21A 0.9500 . ?
C22 C23 1.375(6) . ?
C22 H22A 0.9500 . ?
C23 C24 1.386(5) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?
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 C1 C2 C3 -1.8(6) . . . . ?
Se1 C1 C2 C3 179.8(3) . . . . ?
C1 C2 C3 C4 -0.4(7) . . . . ?
C2 C3 C4 C5 2.0(7) . . . . ?
C3 C4 C5 C6 -1.5(7) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
C2 C1 C6 C5 2.2(6) . . . . ?
Se1 C1 C6 C5 -179.4(3) . . . . ?
C12 N1 C8 C9 -1.5(5) . . . . ?
Cu1 N1 C8 C9 -177.8(3) . . . . ?
C12 N1 C8 C7 176.7(3) . . . . ?
Cu1 N1 C8 C7 0.5(4) . . . . ?
Se1 C7 C8 N1 41.2(4) . . . . ?
Se1 C7 C8 C9 -140.6(3) . . . . ?
N1 C8 C9 C10 2.0(5) . . . . ?
C7 C8 C9 C10 -176.3(3) . . . . ?
C8 C9 C10 C11 -0.7(6) . . . . ?
C9 C10 C11 C12 -1.0(6) . . . . ?
C8 N1 C12 C11 -0.2(6) . . . . ?
Cu1 N1 C12 C11 176.3(3) . . . . ?
C10 C11 C12 N1 1.5(6) . . . . ?
C18 C13 C14 C15 0.1(6) . . . . ?
Se2 C13 C14 C15 178.3(3) . . . . ?
C13 C14 C15 C16 1.3(6) . . . . ?
C14 C15 C16 C17 -1.2(6) . . . . ?
C15 C16 C17 C18 -0.3(6) . . . . ?
C16 C17 C18 C13 1.6(6) . . . . ?
C14 C13 C18 C17 -1.5(6) . . . . ?
Se2 C13 C18 C17 -179.6(3) . . . . ?
C24 N2 C20 C21 2.1(5) . . . . ?
Cu2 N2 C20 C21 -175.9(3) . . . . ?
C24 N2 C20 C19 -175.0(3) . . . . ?
Cu2 N2 C20 C19 7.0(4) . . . . ?
Se2 C19 C20 N2 -47.0(4) . . . . ?
Se2 C19 C20 C21 135.8(3) . . . . ?
N2 C20 C21 C22 -2.9(5) . . . . ?
C19 C20 C21 C22 174.2(3) . . . . ?
C20 C21 C22 C23 1.1(6) . . . . ?
C21 C22 C23 C24 1.4(6) . . . . ?
C20 N2 C24 C23 0.5(5) . . . . ?
Cu2 N2 C24 C23 178.6(3) . . . . ?
C22 C23 C24 N2 -2.3(6) . . . . ?
