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#$Date: 2021-12-10 10:16:28 +0100 (Fri 10 de Dec de 2021) $
#$Revision: 271325 $
#$URL: svn://www.crystallography.net/cod/cif/1/56/56/1565659.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_1565659
loop_
_publ_author_name
'Shakirova, Olga'
'Protsenko, Alexandra'
'Protsenko, Alexander'
'Kuratieva, Natalia'
'Fowles, Samantha'
'Turnbull, Mark M.'
_publ_section_title
;
 Syntheses, structures and properties of copper(II) and cobalt(II)
 complexes with 5(3)-amino-2-chloro-3(5)-methylpyridine isomer cations
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119246
_journal_paper_doi               10.1016/j.ica.2019.119246
_journal_volume                  500
_journal_year                    2020
_chemical_formula_moiety         'C9 H12 Cl4 Cu N2'
_chemical_formula_sum            'C9 H12 Cl4 Cu N2'
_chemical_formula_weight         353.55
_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
_cell_angle_alpha                105.909(9)
_cell_angle_beta                 102.298(9)
_cell_angle_gamma                111.663(10)
_cell_formula_units_Z            2
_cell_length_a                   8.732(3)
_cell_length_b                   9.132(3)
_cell_length_c                   9.792(3)
_cell_measurement_reflns_used    3342
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      2.31
_cell_volume                     653.3(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 25
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Apex DUO CCD area-detector'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5610
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         27.194
_diffrn_reflns_theta_min         2.310
_exptl_absorpt_coefficient_mu    2.462
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_description       prism
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0228
_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)+(0.0257P)²+0.1506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0571
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2587
_reflns_number_total             2883
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ICA-2020-500-119246.cif
_cod_data_source_block           shak120
_cod_original_cell_volume        653.4(4)
_cod_database_code               1565659
_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   0.694
_shelx_estimated_absorpt_t_max   0.866
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 0.29427(3) 0.33099(3) 0.79909(2) 0.01281(7) Uani 1 1 d . . . . .
Cl1 Cl 0.19342(5) 0.02320(6) 0.49243(5) 0.01735(11) Uani 1 1 d . . . . .
Cl2 Cl 0.43875(6) 0.28217(7) 0.99003(5) 0.02061(11) Uani 1 1 d . . . . .
Cl3 Cl 0.18603(6) 0.41448(7) 0.61635(5) 0.02019(11) Uani 1 1 d . . . . .
Cl4 Cl 0.06340(5) 0.29996(6) 0.87675(5) 0.01732(11) Uani 1 1 d . . . . .
N1 N 0.46354(19) 0.3020(2) 0.69039(16) 0.0125(3) Uani 1 1 d . . . . .
N2 N 0.92635(19) 0.5388(2) 0.73980(16) 0.0144(3) Uani 1 1 d . . . . .
H2 H 1.0028 0.4973 0.7438 0.017 Uiso 1 1 calc R U . . .
C1 C 0.4057(2) 0.1811(2) 0.55112(19) 0.0123(3) Uani 1 1 d . . . . .
C2 C 0.5085(2) 0.1737(2) 0.45967(19) 0.0133(4) Uani 1 1 d . . . . .
C3 C 0.6830(2) 0.2957(2) 0.52495(19) 0.0136(4) Uani 1 1 d . . . . .
H3 H 0.7606 0.2960 0.4700 0.016 Uiso 1 1 calc R U . . .
C4 C 0.7448(2) 0.4178(2) 0.67081(19) 0.0128(3) Uani 1 1 d . . . . .
C5 C 0.6322(2) 0.4187(2) 0.75126(19) 0.0135(4) Uani 1 1 d . . . . .
H5 H 0.6756 0.5032 0.8507 0.016 Uiso 1 1 calc R U . . .
C6 C 0.4358(2) 0.0465(3) 0.29750(19) 0.0181(4) Uani 1 1 d . . . . .
H6A H 0.4117 0.1015 0.2283 0.027 Uiso 1 1 calc R U . . .
H6B H 0.3266 -0.0512 0.2812 0.027 Uiso 1 1 calc R U . . .
H6C H 0.5221 0.0069 0.2781 0.027 Uiso 1 1 calc R U . . .
C7 C 0.9897(2) 0.7032(2) 0.79701(19) 0.0158(4) Uani 1 1 d . . . . .
C8 C 1.1827(3) 0.8074(3) 0.8728(2) 0.0276(5) Uani 1 1 d . . . . .
H8A H 1.2394 0.7323 0.8629 0.041 Uiso 1 1 calc R U . . .
H8B H 1.2100 0.8709 0.9805 0.041 Uiso 1 1 calc R U . . .
H8C H 1.2263 0.8881 0.8253 0.041 Uiso 1 1 calc R U . . .
C9 C 0.8760(3) 0.7903(3) 0.7899(2) 0.0209(4) Uani 1 1 d . . . . .
H9A H 0.7710 0.7208 0.6979 0.031 Uiso 1 1 calc R U . . .
H9B H 0.9414 0.9025 0.7880 0.031 Uiso 1 1 calc R U . . .
H9C H 0.8405 0.8049 0.8792 0.031 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'
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'
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
N1 Cu1 Cl4 166.32(5) . .
N1 Cu1 Cl2 89.22(5) . .
Cl4 Cu1 Cl2 94.02(3) . .
N1 Cu1 Cl3 87.08(5) . .
Cl4 Cu1 Cl3 91.29(3) . .
Cl2 Cu1 Cl3 171.74(2) . .
C5 N1 C1 118.83(14) . .
C5 N1 Cu1 118.98(11) . .
C1 N1 Cu1 121.68(12) . .
C7 N2 C4 126.46(16) . .
C7 N2 H2 116.8 . .
C4 N2 H2 116.8 . .
N1 C1 C2 124.40(16) . .
N1 C1 Cl1 114.94(13) . .
C2 C1 Cl1 120.58(14) . .
C3 C2 C1 115.76(16) . .
C3 C2 C6 120.78(15) . .
C1 C2 C6 123.42(16) . .
C2 C3 C4 119.97(16) . .
C2 C3 H3 120.0 . .
C4 C3 H3 120.0 . .
C5 C4 C3 120.31(17) . .
C5 C4 N2 119.95(15) . .
C3 C4 N2 119.71(15) . .
N1 C5 C4 120.63(16) . .
N1 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C2 C6 H6A 109.5 . .
C2 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C2 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N2 C7 C8 118.39(17) . .
N2 C7 C9 122.35(17) . .
C8 C7 C9 119.25(18) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 2.0477(15) .
Cu1 Cl4 2.2522(8) .
Cu1 Cl2 2.2701(7) .
Cu1 Cl3 2.2882(7) .
Cl1 C1 1.7217(19) .
N1 C5 1.334(2) .
N1 C1 1.343(2) .
N2 C7 1.291(2) .
N2 C4 1.425(2) .
N2 H2 0.8800 .
C1 C2 1.402(2) .
C2 C3 1.383(3) .
C2 C6 1.513(2) .
C3 C4 1.389(2) .
C3 H3 0.9500 .
C4 C5 1.386(2) .
C5 H5 0.9500 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C8 1.481(3) .
C7 C9 1.486(3) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
