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#$Date: 2022-03-07 10:14:33 +0200 (Mon, 07 Mar 2022) $
#$Revision: 273478 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/46/8104650.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_8104650
loop_
_publ_author_name
'Jaćimović, Željko K.'
'Tomić, Zoran D.'
'Giester, Gerald'
'Libowitzky, Eugen'
'Ajanović, Atifa'
'Kosović, Milica'
_publ_section_title
;
 The crystal structure of bis[4-bromo-2-(1H-pyrazol-3-yl) phenolato-κ2
 N,O] copper(II), C18H12Br2CuN4O2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1003
_journal_page_last               1005
_journal_paper_doi               10.1515/ncrs-2021-0191
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C18 H12 Br2 Cu N4 O2'
_chemical_formula_sum            'C18 H12 Br2 Cu N4 O2'
_chemical_formula_weight         539.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 105.639(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5165(11)
_cell_length_b                   5.4369(5)
_cell_length_c                   14.4872(14)
_cell_measurement_reflns_used    7616
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.18
_cell_measurement_theta_min      2.64
_cell_volume                     873.52(14)
_computing_cell_refinement       'APEX2 (Bruker, 2008)'
_computing_data_collection       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 2012), Mercury (Macrae, 2020)'
_computing_publication_material  'PLATON (Spek, 2003), WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker ApexII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24890
_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         30.623
_diffrn_reflns_theta_min         1.836
_exptl_absorpt_coefficient_mu    5.847
_exptl_absorpt_correction_type   "'partial multi scans'"
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    2.052
_exptl_crystal_description       prism
_exptl_crystal_F_000             526
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0232
_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)+(0.0240P)²+0.5488P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0528
_refine_ls_wR_factor_ref         0.0559
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2239
_reflns_number_total             2680
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0191_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8104650
_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.
;
_shelxl_version_number           2013-2
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'
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
Br1 Br 0.92682(2) 0.29323(4) 0.29381(2) 0.03565(7) Uani 1 1 d . . . . .
C1 C 0.71540(16) 0.8184(3) 0.45057(13) 0.0247(3) Uani 1 1 d . . . . .
C2 C 0.83933(18) 0.8481(4) 0.45822(16) 0.0351(4) Uani 1 1 d . . . . .
C3 C 0.90086(18) 0.6939(4) 0.41266(17) 0.0364(5) Uani 1 1 d . . . . .
C4 C 0.84106(17) 0.5011(3) 0.35819(13) 0.0271(4) Uani 1 1 d . . . . .
C5 C 0.72055(16) 0.4605(3) 0.34963(12) 0.0247(3) Uani 1 1 d . . . . .
C6 C 0.65605(15) 0.6163(3) 0.39524(11) 0.0213(3) Uani 1 1 d . . . . .
C7 C 0.52762(15) 0.5696(3) 0.38121(11) 0.0211(3) Uani 1 1 d . . . . .
C8 C 0.45589(16) 0.3758(3) 0.33160(12) 0.0260(4) Uani 1 1 d . . . . .
C9 C 0.34164(16) 0.4199(4) 0.33940(13) 0.0270(4) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 1.0000 0.5000 0.02228(7) Uani 1 2 d S . P . .
H1 H 0.295(2) 0.704(5) 0.4089(17) 0.037(7) Uiso 1 1 d . . . . .
H2 H 0.2671 0.3376 0.3185 0.032 Uiso 1 1 d R U . . .
H3 H 0.4793 0.2475 0.2959 0.031 Uiso 1 1 d R U . . .
H4 H 0.6821 0.3254 0.3085 0.030 Uiso 1 1 d R U . . .
H5 H 0.9829 0.7163 0.4192 0.044 Uiso 1 1 d R U . . .
H6 H 0.8764 0.9900 0.4923 0.042 Uiso 1 1 d R U . . .
N1 N 0.45866(13) 0.7188(3) 0.41696(10) 0.0227(3) Uani 1 1 d . . . . .
N2 N 0.34578(14) 0.6249(3) 0.39083(11) 0.0258(3) Uani 1 1 d . . . . .
O1 O 0.66406(11) 0.9777(2) 0.49569(10) 0.0290(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'
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'
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'
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
O1 Cu1 O1 180.0 3_676 .
O1 Cu1 N1 90.54(6) 3_676 3_676
O1 Cu1 N1 89.46(6) . 3_676
O1 Cu1 N1 89.47(6) 3_676 .
O1 Cu1 N1 90.53(6) . .
N1 Cu1 N1 180.0 3_676 .
C1 O1 Cu1 129.63(11) . .
C7 N1 N2 106.85(14) . .
C7 N1 Cu1 130.78(12) . .
N2 N1 Cu1 122.15(12) . .
C9 N2 N1 111.02(16) . .
C9 N2 H1 133.9(17) . .
N1 N2 H1 115.1(17) . .
C5 C4 C3 120.59(17) . .
C5 C4 Br1 120.28(14) . .
C3 C4 Br1 119.13(14) . .
O1 C1 C2 117.75(16) . .
O1 C1 C6 125.17(16) . .
C2 C1 C6 117.08(17) . .
N2 C9 C8 107.54(16) . .
N2 C9 H2 117.9 . .
C8 C9 H2 134.5 . .
C2 C3 C4 119.68(18) . .
C2 C3 H5 120.7 . .
C4 C3 H5 119.6 . .
C3 C2 C1 122.26(18) . .
C3 C2 H6 121.7 . .
C1 C2 H6 115.8 . .
N1 C7 C8 108.91(15) . .
N1 C7 C6 121.81(15) . .
C8 C7 C6 129.28(16) . .
C4 C5 C6 120.59(16) . .
C4 C5 H4 117.2 . .
C6 C5 H4 122.2 . .
C5 C6 C1 119.78(15) . .
C5 C6 C7 118.31(15) . .
C1 C6 C7 121.87(16) . .
C9 C8 C7 105.69(16) . .
C9 C8 H3 126.3 . .
C7 C8 H3 127.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C4 1.9025(18) .
Cu1 O1 1.9111(13) 3_676
Cu1 O1 1.9111(13) .
Cu1 N1 1.9241(14) 3_676
Cu1 N1 1.9241(14) .
O1 C1 1.317(2) .
N1 C7 1.334(2) .
N1 N2 1.352(2) .
N2 C9 1.335(2) .
N2 H1 0.82(2) .
C4 C5 1.378(3) .
C4 C3 1.379(3) .
C1 C2 1.411(3) .
C1 C6 1.421(2) .
C9 C8 1.372(3) .
C9 H2 0.9422 .
C3 C2 1.376(3) .
C3 H5 0.9313 .
C2 H6 0.9529 .
C7 C8 1.411(2) .
C7 C6 1.460(2) .
C5 C6 1.404(2) .
C5 H4 0.9736 .
C8 H3 0.9496 .
