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#$Date: 2023-09-05 22:55:13 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286135 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/82/1568242.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_1568242
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 Br4 Cu2 N2 O2 Se2'
_chemical_formula_sum            'C24 H22 Br4 Cu2 N2 O2 Se2'
_chemical_formula_weight         975.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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
;
2023-01-05 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.666(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1270(8)
_cell_length_b                   13.0444(15)
_cell_length_c                   14.4480(17)
_cell_measurement_reflns_used    4818
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.86
_cell_volume                     1509.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0668
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22506
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_min         2.117
_exptl_absorpt_coefficient_mu    9.136
_exptl_absorpt_correction_T_max  0.336
_exptl_absorpt_correction_T_min  0.132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    2.145
_exptl_crystal_description       plate
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.130
_refine_diff_density_max         1.062
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0381
_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)+(0.0531P)²+2.4087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2446
_reflns_number_total             3077
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2fd00160h1.cif
_cod_data_source_block           AO1
_cod_depositor_comments
'Adding full bibliography for 1568240--1568243.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1568242
_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   0.184
_shelx_estimated_absorpt_t_max   0.383
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.56971(8) 0.39735(5) 0.54842(4) 0.02330(17) Uani 1 1 d . . . . .
Br1 Br 0.84857(7) 0.49521(5) 0.62212(4) 0.03039(16) Uani 1 1 d . . . . .
Br2 Br 0.61159(8) 0.24008(5) 0.47248(4) 0.03712(18) Uani 1 1 d . . . . .
Se1 Se 0.75819(6) 0.47926(4) 0.39112(4) 0.02190(14) Uani 1 1 d . . . . .
O1 O 0.5691(4) 0.4767(3) 0.4320(3) 0.0232(8) Uani 1 1 d . . . . .
N1 N 0.5277(6) 0.3341(4) 0.6664(3) 0.0254(10) Uani 1 1 d . . . . .
C1 C 0.6594(7) 0.3012(5) 0.7288(4) 0.0310(13) Uani 1 1 d . . . . .
H1 H 0.767627 0.303875 0.712187 0.037 Uiso 1 1 calc R U . . .
C2 C 0.6420(9) 0.2637(5) 0.8160(5) 0.0385(15) Uani 1 1 d . . . . .
H2 H 0.736358 0.239536 0.858246 0.046 Uiso 1 1 calc R U . . .
C3 C 0.4861(8) 0.2621(5) 0.8408(4) 0.0336(13) Uani 1 1 d . . . . .
H3 H 0.471641 0.238170 0.901034 0.040 Uiso 1 1 calc R U . . .
C4 C 0.3498(8) 0.2957(4) 0.7770(4) 0.0298(12) Uani 1 1 d . . . . .
H4 H 0.240944 0.294351 0.792665 0.036 Uiso 1 1 calc R U . . .
C5 C 0.3748(7) 0.3314(4) 0.6898(4) 0.0245(11) Uani 1 1 d . . . . .
C6 C 0.6773(7) 0.4496(4) 0.2593(4) 0.0260(11) Uani 1 1 d . . . . .
C7 C 0.5106(8) 0.4253(5) 0.2330(5) 0.0397(15) Uani 1 1 d . . . . .
H7 H 0.437032 0.425739 0.277596 0.048 Uiso 1 1 calc R U . . .
C8 C 0.4532(10) 0.4001(6) 0.1395(5) 0.0505(19) Uani 1 1 d . . . . .
H8 H 0.339155 0.383061 0.119236 0.061 Uiso 1 1 calc R U . . .
C9 C 0.5637(11) 0.4002(5) 0.0766(5) 0.0513(19) Uani 1 1 d . . . . .
H9 H 0.524254 0.383836 0.012630 0.062 Uiso 1 1 calc R U . . .
C10 C 0.7297(10) 0.4234(6) 0.1046(4) 0.0460(17) Uani 1 1 d . . . . .
H10 H 0.803734 0.422213 0.060261 0.055 Uiso 1 1 calc R U . . .
C11 C 0.7894(9) 0.4484(5) 0.1976(4) 0.0377(14) Uani 1 1 d . . . . .
H11 H 0.903814 0.464275 0.217936 0.045 Uiso 1 1 calc R U . . .
C12 C 0.2325(6) 0.3700(4) 0.6199(4) 0.0248(11) Uani 1 1 d . . . . .
H12A H 0.126051 0.349917 0.639545 0.030 Uiso 1 1 calc R U . . .
H12B H 0.236332 0.338433 0.558015 0.030 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'
N N 0.0061 0.0033 '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'
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'
O O 0.0106 0.0060 '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 O1 168.12(17) . . ?
N1 Cu1 O1 92.14(17) . 3_666 ?
O1 Cu1 O1 76.90(16) . 3_666 ?
N1 Cu1 Br2 95.53(14) . . ?
O1 Cu1 Br2 92.26(11) . . ?
O1 Cu1 Br2 152.18(11) 3_666 . ?
N1 Cu1 Br1 96.56(14) . . ?
O1 Cu1 Br1 88.25(11) . . ?
O1 Cu1 Br1 90.69(11) 3_666 . ?
Br2 Cu1 Br1 114.83(3) . . ?
O1 Se1 C6 99.0(2) . . ?
O1 Se1 C12 95.42(19) . 3_666 ?
C6 Se1 C12 97.5(2) . 3_666 ?
Se1 O1 Cu1 115.09(18) . . ?
Se1 O1 Cu1 125.0(2) . 3_666 ?
Cu1 O1 Cu1 103.10(16) . 3_666 ?
C5 N1 C1 119.2(5) . . ?
C5 N1 Cu1 122.0(4) . . ?
C1 N1 Cu1 118.5(4) . . ?
N1 C1 C2 122.1(5) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 118.9(6) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.3(6) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 119.1(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.3(5) . . ?
N1 C5 C12 117.8(5) . . ?
C4 C5 C12 120.8(5) . . ?
C11 C6 C7 123.0(6) . . ?
C11 C6 Se1 119.0(4) . . ?
C7 C6 Se1 118.0(4) . . ?
C6 C7 C8 118.3(6) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
C9 C8 C7 119.3(7) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 121.4(6) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 120.2(6) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C6 C11 C10 117.9(6) . . ?
C6 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C5 C12 Se1 110.8(4) . 3_666 ?
C5 C12 H12A 109.5 . . ?
Se1 C12 H12A 109.5 3_666 . ?
C5 C12 H12B 109.5 . . ?
Se1 C12 H12B 109.5 3_666 . ?
H12A C12 H12B 108.1 . . ?
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 1.974(4) . ?
Cu1 O1 1.974(4) . ?
Cu1 O1 2.039(4) 3_666 ?
Cu1 Br2 2.3777(9) . ?
Cu1 Br1 2.6625(9) . ?
Se1 O1 1.737(3) . ?
Se1 C6 1.947(5) . ?
Se1 C12 1.975(5) 3_666 ?
N1 C5 1.342(7) . ?
N1 C1 1.348(7) . ?
C1 C2 1.381(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.374(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(7) . ?
C4 H4 0.9500 . ?
C5 C12 1.489(8) . ?
C6 C11 1.378(8) . ?
C6 C7 1.381(8) . ?
C7 C8 1.392(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(9) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
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 Se1 O1 Cu1 133.4(2) . . . . ?
C12 Se1 O1 Cu1 -128.1(2) 3_666 . . . ?
C6 Se1 O1 Cu1 -97.3(3) . . . 3_666 ?
C12 Se1 O1 Cu1 1.2(3) 3_666 . . 3_666 ?
C5 N1 C1 C2 0.7(9) . . . . ?
Cu1 N1 C1 C2 174.6(5) . . . . ?
N1 C1 C2 C3 -1.5(10) . . . . ?
C1 C2 C3 C4 1.5(9) . . . . ?
C2 C3 C4 C5 -0.7(9) . . . . ?
C1 N1 C5 C4 0.1(8) . . . . ?
Cu1 N1 C5 C4 -173.6(4) . . . . ?
C1 N1 C5 C12 178.9(5) . . . . ?
Cu1 N1 C5 C12 5.2(7) . . . . ?
C3 C4 C5 N1 -0.1(8) . . . . ?
C3 C4 C5 C12 -178.8(5) . . . . ?
C11 C6 C7 C8 -1.0(10) . . . . ?
Se1 C6 C7 C8 -177.6(5) . . . . ?
C6 C7 C8 C9 0.0(10) . . . . ?
C7 C8 C9 C10 0.8(11) . . . . ?
C8 C9 C10 C11 -0.7(11) . . . . ?
C7 C6 C11 C10 1.2(10) . . . . ?
Se1 C6 C11 C10 177.7(5) . . . . ?
C9 C10 C11 C6 -0.3(10) . . . . ?
N1 C5 C12 Se1 -71.5(5) . . . 3_666 ?
C4 C5 C12 Se1 107.2(5) . . . 3_666 ?
