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#$Date: 2022-03-31 10:20:30 +0300 (Thu, 31 Mar 2022) $
#$Revision: 274160 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/49/8104966.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_8104966
loop_
_publ_author_name
'Duan, Rui'
'Ma, Xun'
'Huang, Meifen'
'Wang, Man'
'Wu, Qiong'
_publ_section_title
;
 Crystal structure of
 [6,6′-(((2,2-dimethylpropane-1,3-diyl)bis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato)-κ4N,N′,O,O′]copper(II)
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              79
_journal_page_last               80
_journal_paper_doi               10.1515/ncrs-2021-0376
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C19 H18 Cl2 Cu N2 O2'
_chemical_formula_sum            'C19 H18 Cl2 Cu N2 O2'
_chemical_formula_weight         440.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 100.725(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.010(3)
_cell_length_b                   11.3886(15)
_cell_length_c                   7.9578(10)
_cell_measurement_reflns_used    2781
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      26.11
_cell_measurement_theta_min      3.45
_cell_volume                     1870.8(4)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8248
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.464
_diffrn_reflns_theta_min         1.973
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.469
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear greenish black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.179
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0778P)²+4.4047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1620
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1526
_reflns_number_total             1902
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0376_suppl.cif
_cod_data_source_block           mx44
_cod_database_code               8104966
_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_max   0.843
_shelx_estimated_absorpt_t_min   0.758
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.000000 0.01438(6) 0.250000 0.0261(3) Uani 1 2 d S T P . .
Cl1 Cl 0.13532(5) -0.32244(10) 0.27252(16) 0.0388(3) Uani 1 1 d . . . . .
O1 O 0.06290(13) -0.1035(3) 0.2386(4) 0.0297(7) Uani 1 1 d . . . . .
N1 N 0.04804(16) 0.1346(3) 0.1521(4) 0.0293(8) Uani 1 1 d . . . . .
C1 C 0.1442(2) 0.0173(4) 0.1451(5) 0.0275(9) Uani 1 1 d . . . . .
C2 C 0.11978(19) -0.0901(4) 0.1992(5) 0.0274(9) Uani 1 1 d . . . . .
C3 C 0.1624(2) -0.1881(4) 0.2091(5) 0.0305(10) Uani 1 1 d . . . . .
C4 C 0.2242(2) -0.1796(4) 0.1709(6) 0.0347(11) Uani 1 1 d . . . . .
H4 H 0.251430 -0.246814 0.181136 0.042 Uiso 1 1 calc R U . . .
C5 C 0.2461(2) -0.0744(5) 0.1184(6) 0.0394(12) Uani 1 1 d . . . . .
H5 H 0.288190 -0.069007 0.091237 0.047 Uiso 1 1 calc R U . . .
C6 C 0.2068(2) 0.0227(5) 0.1055(6) 0.0368(11) Uani 1 1 d . . . . .
H6 H 0.222149 0.095143 0.069167 0.044 Uiso 1 1 calc R U . . .
C7 C 0.1052(2) 0.1211(4) 0.1174(5) 0.0293(9) Uani 1 1 d . . . . .
H7 H 0.123246 0.186522 0.068779 0.035 Uiso 1 1 calc R U . . .
C8 C 0.0122(2) 0.2433(4) 0.0982(5) 0.0280(9) Uani 1 1 d . . . . .
H8A H -0.030023 0.222788 0.026076 0.034 Uiso 1 1 calc R U . . .
H8B H 0.036864 0.290208 0.027509 0.034 Uiso 1 1 calc R U . . .
C9 C 0.000000 0.3188(6) 0.250000 0.0314(14) Uani 1 2 d S T P . .
C10 C -0.0596(3) 0.3944(5) 0.1857(7) 0.0518(14) Uani 1 1 d . . . . .
H10A H -0.052208 0.441473 0.088005 0.078 Uiso 1 1 calc R U . . .
H10B H -0.067401 0.446689 0.277602 0.078 Uiso 1 1 calc R U . . .
H10C H -0.097360 0.343683 0.150312 0.078 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'
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 89.95(17) 2 .
O1 Cu1 N1 93.50(14) . .
O1 Cu1 N1 159.03(14) 2 .
O1 Cu1 N1 159.03(14) . 2
O1 Cu1 N1 93.50(14) 2 2
N1 Cu1 N1 90.7(2) . 2
C2 O1 Cu1 127.4(3) . .
C7 N1 Cu1 125.0(3) . .
C7 N1 C8 119.0(4) . .
C8 N1 Cu1 115.6(2) . .
C2 C1 C7 121.9(4) . .
C6 C1 C2 120.6(4) . .
C6 C1 C7 117.4(4) . .
O1 C2 C1 125.0(4) . .
O1 C2 C3 119.4(4) . .
C1 C2 C3 115.6(4) . .
C2 C3 Cl1 118.0(3) . .
C4 C3 Cl1 119.6(3) . .
C4 C3 C2 122.4(4) . .
C3 C4 H4 119.8 . .
C5 C4 C3 120.4(4) . .
C5 C4 H4 119.8 . .
C4 C5 H5 120.2 . .
C6 C5 C4 119.6(4) . .
C6 C5 H5 120.2 . .
C1 C6 H6 119.3 . .
C5 C6 C1 121.5(5) . .
C5 C6 H6 119.3 . .
N1 C7 C1 126.4(4) . .
N1 C7 H7 116.8 . .
C1 C7 H7 116.8 . .
N1 C8 H8A 109.0 . .
N1 C8 H8B 109.0 . .
N1 C8 C9 113.1(3) . .
H8A C8 H8B 107.8 . .
C9 C8 H8A 109.0 . .
C9 C8 H8B 109.0 . .
C8 C9 C8 112.2(5) 2 .
C10 C9 C8 109.4(3) 2 .
C10 C9 C8 109.4(3) . 2
C10 C9 C8 107.3(3) 2 2
C10 C9 C8 107.3(3) . .
C10 C9 C10 111.3(6) 2 .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10B 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.898(3) 2
Cu1 O1 1.898(3) .
Cu1 N1 1.948(4) .
Cu1 N1 1.948(4) 2
Cl1 C3 1.739(5) .
O1 C2 1.300(5) .
N1 C7 1.291(5) .
N1 C8 1.471(5) .
C1 C2 1.424(6) .
C1 C6 1.410(6) .
C1 C7 1.431(6) .
C2 C3 1.424(6) .
C3 C4 1.391(6) .
C4 H4 0.9500 .
C4 C5 1.377(7) .
C5 H5 0.9500 .
C5 C6 1.373(7) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C8 C9 1.542(5) .
C9 C10 1.527(6) 2
C9 C10 1.527(6) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
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
Cu1 O1 C2 C1 -4.4(6) . . . .
Cu1 O1 C2 C3 175.6(3) . . . .
Cu1 N1 C7 C1 -0.6(6) . . . .
Cu1 N1 C8 C9 71.4(4) . . . .
Cl1 C3 C4 C5 179.2(4) . . . .
O1 Cu1 O1 C2 167.4(4) 2 . . .
O1 C2 C3 Cl1 0.5(5) . . . .
O1 C2 C3 C4 -179.2(4) . . . .
N1 Cu1 O1 C2 8.1(3) . . . .
N1 Cu1 O1 C2 -92.9(5) 2 . . .
N1 C8 C9 C8 -35.3(2) . . . 2
N1 C8 C9 C10 -155.5(4) . . . .
N1 C8 C9 C10 83.6(5) . . . 2
C1 C2 C3 Cl1 -179.4(3) . . . .
C1 C2 C3 C4 0.9(6) . . . .
C2 C1 C6 C5 -0.3(7) . . . .
C2 C1 C7 N1 7.1(7) . . . .
C2 C3 C4 C5 -1.2(7) . . . .
C3 C4 C5 C6 0.7(7) . . . .
C4 C5 C6 C1 0.0(7) . . . .
C6 C1 C2 O1 179.9(4) . . . .
C6 C1 C2 C3 -0.2(6) . . . .
C6 C1 C7 N1 -177.1(4) . . . .
C7 N1 C8 C9 -115.0(4) . . . .
C7 C1 C2 O1 -4.5(7) . . . .
C7 C1 C2 C3 175.5(4) . . . .
C7 C1 C6 C5 -176.1(4) . . . .
C8 N1 C7 C1 -173.5(4) . . . .
