#------------------------------------------------------------------------------
#$Date: 2021-12-10 10:16:28 +0100 (Fri 10 de Dec de 2021) $
#$Revision: 271325 $
#$URL: svn://www.crystallography.net/cod/cif/1/56/56/1565656.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_1565656
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         '2(C6 H8 Cl N2), Cl4 Cu'
_chemical_formula_sum            'C12 H16 Cl6 Cu N4'
_chemical_formula_weight         492.53
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 100.146(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   18.0407(16)
_cell_length_b                   7.3919(6)
_cell_length_c                   7.3131(5)
_cell_measurement_reflns_used    4795
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.98
_cell_volume                     959.99(13)
_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      296(2)
_diffrn_detector_area_resol_mean 25
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Nonius X8Apex 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  0.0345
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7803
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         3.586
_exptl_absorpt_coefficient_mu    1.974
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_description       plate
_exptl_crystal_F_000             494
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1953
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.189
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0259
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0160P)²+0.7806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0639
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1784
_reflns_number_total             1953
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ICA-2020-500-119246.cif
_cod_data_source_block           shak101
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1565656
_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   0.562
_shelx_estimated_absorpt_t_max   0.827
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
Cu1 Cu 0.0000 0.5000 0.5000 0.02420(11) Uani 1 2 d S . P . .
Cl1 Cl 0.01904(3) 0.28923(7) 0.27994(7) 0.03370(14) Uani 1 1 d . . . . .
Cl2 Cl 0.12625(3) 0.54738(8) 0.57256(8) 0.03648(14) Uani 1 1 d . . . . .
Cl3A Cl 0.4420(4) 0.3337(10) 0.2138(11) 0.0752(9) Uani 0.418(11) 1 d . U P A 1
Cl3B Cl 0.4492(3) 0.3908(9) 0.1883(8) 0.0752(9) Uani 0.582(11) 1 d . . P A 2
N1 N 0.30984(14) 0.3340(4) 0.0195(3) 0.0615(7) Uani 1 1 d . . . . .
N2 N 0.12286(10) 0.5218(3) 0.0484(3) 0.0376(4) Uani 1 1 d . . . . .
H2A H 0.0998 0.4601 0.1266 0.056 Uiso 1 1 calc R U . . .
H2B H 0.1050 0.4873 -0.0676 0.056 Uiso 1 1 calc R U . . .
H2C H 0.1145 0.6396 0.0602 0.056 Uiso 1 1 calc R U . . .
C1 C 0.23610(15) 0.3695(4) -0.0148(4) 0.0484(6) Uani 1 1 d . . . . .
H1 H 0.2059 0.3124 -0.1144 0.058 Uiso 1 1 calc R U . . .
C2 C 0.20387(12) 0.4865(3) 0.0912(3) 0.0284(4) Uani 1 1 d . . . . .
C3 C 0.24795(12) 0.5707(3) 0.2399(3) 0.0342(5) Uani 1 1 d . . . . .
H3 H 0.2264 0.6514 0.3128 0.041 Uiso 1 1 calc R U . . .
C4 C 0.32402(13) 0.5350(3) 0.2805(3) 0.0382(5) Uani 1 1 d . . . . .
C5 C 0.35080(14) 0.4168(4) 0.1620(4) 0.0460(6) Uani 1 1 d . . . . .
C6 C 0.37410(18) 0.6196(5) 0.4449(5) 0.0766(11) Uani 1 1 d . . . B 1
H6C H 0.4104 0.6966 0.4022 0.115 Uiso 1 1 calc R U . B 1
H6B H 0.3998 0.5262 0.5226 0.115 Uiso 1 1 calc R U . B 1
H6A H 0.3441 0.6898 0.5147 0.115 Uiso 1 1 calc R U . B 1
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
Cl2 Cu1 Cl2 180.0 . 3_566
Cl2 Cu1 Cl1 90.04(2) . .
Cl2 Cu1 Cl1 89.96(2) 3_566 .
Cl2 Cu1 Cl1 89.96(2) . 3_566
Cl2 Cu1 Cl1 90.04(2) 3_566 3_566
Cl1 Cu1 Cl1 180.0 . 3_566
C5 N1 C1 117.3(2) . .
C2 N2 H2A 109.5 . .
C2 N2 H2B 109.5 . .
H2A N2 H2B 109.5 . .
C2 N2 H2C 109.5 . .
H2A N2 H2C 109.5 . .
H2B N2 H2C 109.5 . .
N1 C1 C2 122.0(2) . .
N1 C1 H1 119.0 . .
C2 C1 H1 119.0 . .
C1 C2 C3 119.5(2) . .
C1 C2 N2 120.2(2) . .
C3 C2 N2 120.28(19) . .
C4 C3 C2 119.9(2) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C5 C4 C3 115.6(2) . .
C5 C4 C6 122.6(2) . .
C3 C4 C6 121.8(2) . .
N1 C5 C4 125.6(2) . .
N1 C5 Cl3A 112.8(3) . .
C4 C5 Cl3A 120.8(3) . .
N1 C5 Cl3B 116.7(3) . .
C4 C5 Cl3B 117.3(3) . .
C4 C6 H6C 109.5 . .
C4 C6 H6B 109.5 . .
H6C C6 H6B 109.5 . .
C4 C6 H6A 109.5 . .
H6C C6 H6A 109.5 . .
H6B C6 H6A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cl2 2.2728(5) .
Cu1 Cl2 2.2729(5) 3_566
Cu1 Cl1 2.3087(5) .
Cu1 Cl1 2.3087(5) 3_566
Cl3A C5 1.734(7) .
Cl3B C5 1.762(5) .
N1 C5 1.317(3) .
N1 C1 1.336(3) .
N2 C2 1.463(3) .
N2 H2A 0.8900 .
N2 H2B 0.8900 .
N2 H2C 0.8900 .
C1 C2 1.359(3) .
C1 H1 0.9300 .
C2 C3 1.377(3) .
C3 C4 1.378(3) .
C3 H3 0.9300 .
C4 C5 1.377(4) .
C4 C6 1.506(3) .
C6 H6C 0.9600 .
C6 H6B 0.9600 .
C6 H6A 0.9600 .
