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#$Date: 2022-06-27 11:14:12 +0300 (Mon, 27 Jun 2022) $
#$Revision: 276273 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105521.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_8105521
loop_
_publ_author_name
'Ju, Hongping'
'Li, Meihua'
'Chen, Zihao'
'Wu, Qiong'
'Chai, Yanling'
_publ_section_title
;
 Crystal structure of
 (6,6′-((ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato-κ2
 N,O))copper(II), C16H12Cl2CuN2O2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              3
_journal_page_last               4
_journal_paper_doi               10.1515/ncrs-2017-0249
_journal_volume                  234
_journal_year                    2018
_chemical_formula_moiety         'C16 H12 Cl2 Cu N2 O2'
_chemical_formula_sum            'C16 H12 Cl2 Cu N2 O2'
_chemical_formula_weight         398.72
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.8449(5)
_cell_length_b                   12.5266(6)
_cell_length_c                   19.0540(11)
_cell_measurement_reflns_used    2480
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.3360
_cell_measurement_theta_min      3.7480
_cell_volume                     3065.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Diamond 3.2k)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'multiwire proportional'
_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  0.0529
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11780
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.42
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.783
_exptl_absorpt_correction_T_max  0.814
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0509P)²+0.7304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1164
_reflns_number_gt                2003
_reflns_number_total             2695
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0249_suppl.cif
_cod_data_source_block           d10
_cod_database_code               8105521
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C12(H12), C13(H13), C4(H4), C3(H3), C14(H14), C5(H5)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cu1 Cu 0.12642(3) 0.47053(3) 0.49464(3) 0.0370(2) Uani 1 d . . .
Cl2 Cl 0.09318(8) 0.47984(8) 0.24615(6) 0.0553(3) Uani 1 d . . .
Cl1 Cl -0.06125(10) 0.16275(9) 0.41990(7) 0.0708(4) Uani 1 d . . .
O2 O 0.13738(18) 0.48691(19) 0.39622(15) 0.0402(7) Uani 1 d . . .
N1 N 0.1133(2) 0.4639(2) 0.59533(19) 0.0407(8) Uani 1 d . . .
O1 O 0.0393(2) 0.3489(2) 0.48131(15) 0.0467(7) Uani 1 d . . .
N2 N 0.2230(2) 0.5860(2) 0.51383(18) 0.0407(8) Uani 1 d . . .
C16 C 0.1850(3) 0.5625(3) 0.3621(2) 0.0390(9) Uani 1 d . . .
C11 C 0.2484(3) 0.6429(3) 0.3936(2) 0.0395(9) Uani 1 d . . .
C1 C 0.0080(3) 0.2815(3) 0.5296(2) 0.0405(10) Uani 1 d . . .
C6 C 0.0209(3) 0.2947(3) 0.6026(2) 0.0401(9) Uani 1 d . . .
C7 C 0.0701(3) 0.3888(3) 0.6310(2) 0.0453(10) Uani 1 d . . .
H7 H 0.0706 0.3960 0.6806 0.054 Uiso 1 calc . . R
C10 C 0.2626(3) 0.6489(3) 0.4683(2) 0.0411(10) Uani 1 d . . .
H10 H 0.3054 0.7050 0.4854 0.049 Uiso 1 calc . . R
C15 C 0.1747(3) 0.5702(3) 0.2883(2) 0.0414(10) Uani 1 d . . .
C12 C 0.2956(3) 0.7221(3) 0.3520(3) 0.0524(11) Uani 1 d . . .
H12 H 0.3369 0.7754 0.3740 0.063 Uiso 1 calc . . R
C13 C 0.2834(4) 0.7243(3) 0.2809(3) 0.0618(13) Uani 1 d . . .
H13 H 0.3171 0.7775 0.2535 0.074 Uiso 1 calc . . R
C2 C -0.0438(3) 0.1866(3) 0.5083(2) 0.0470(11) Uani 1 d . . .
C9 C 0.2469(3) 0.5974(3) 0.5889(2) 0.0518(11) Uani 1 d . . .
H9A H 0.2620 0.6730 0.6001 0.062 Uiso 1 calc . . R
H9B H 0.3087 0.5540 0.6012 0.062 Uiso 1 calc . . R
C4 C -0.0680(3) 0.1291(4) 0.6267(3) 0.0639(14) Uani 1 d . . .
H4 H -0.0941 0.0781 0.6592 0.077 Uiso 1 calc . . R
C3 C -0.0797(3) 0.1136(4) 0.5569(3) 0.0618(14) Uani 1 d . . .
H3 H -0.1134 0.0507 0.5409 0.074 Uiso 1 calc . . R
C8 C 0.1533(3) 0.5597(3) 0.6295(2) 0.0514(11) Uani 1 d . . .
H8A H 0.1732 0.5435 0.6785 0.062 Uiso 1 calc . . R
H8B H 0.0992 0.6160 0.6301 0.062 Uiso 1 calc . . R
C14 C 0.2211(3) 0.6479(3) 0.2492(2) 0.0546(11) Uani 1 d . . .
H14 H 0.2106 0.6497 0.1998 0.066 Uiso 1 calc . . R
C5 C -0.0181(3) 0.2195(3) 0.6504(3) 0.0532(11) Uani 1 d . . .
H5 H -0.0100 0.2309 0.6994 0.064 Uiso 1 calc . . R
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'
O O 0.0106 0.0060 '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
O2 Cu1 N1 176.18(12) . .
O2 Cu1 O1 89.90(11) . .
O2 Cu1 N2 93.35(13) . .
N1 Cu1 N2 84.30(14) . .
O1 Cu1 N1 92.67(13) . .
O1 Cu1 N2 174.65(13) . .
C16 O2 Cu1 127.5(3) . .
C7 N1 Cu1 126.5(3) . .
C7 N1 C8 121.2(4) . .
C8 N1 Cu1 112.2(3) . .
C1 O1 Cu1 126.9(3) . .
C10 N2 Cu1 125.9(3) . .
C10 N2 C9 121.2(3) . .
C9 N2 Cu1 112.9(3) . .
O2 C16 C11 124.9(4) . .
O2 C16 C15 120.0(3) . .
C15 C16 C11 115.0(3) . .
C16 C11 C10 121.7(4) . .
C12 C11 C16 120.4(4) . .
C12 C11 C10 117.8(4) . .
O1 C1 C6 125.4(4) . .
O1 C1 C2 118.7(4) . .
C6 C1 C2 115.8(4) . .
C1 C6 C7 121.1(4) . .
C5 C6 C1 121.2(4) . .
C5 C6 C7 117.5(4) . .
N1 C7 C6 126.1(4) . .
N2 C10 C11 126.1(4) . .
C16 C15 Cl2 118.1(3) . .
C14 C15 Cl2 118.3(3) . .
C14 C15 C16 123.4(4) . .
C13 C12 C11 121.6(4) . .
C12 C13 C14 119.0(4) . .
C1 C2 Cl1 119.0(3) . .
C3 C2 Cl1 119.8(4) . .
C3 C2 C1 121.2(4) . .
N2 C9 C8 107.6(3) . .
C3 C4 C5 119.5(5) . .
C4 C3 C2 121.8(4) . .
N1 C8 C9 108.1(3) . .
C15 C14 C13 120.4(4) . .
C4 C5 C6 120.4(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.892(3) .
Cu1 N1 1.928(4) .
Cu1 O1 1.908(3) .
Cu1 N2 1.940(3) .
Cl2 C15 1.739(4) .
Cl1 C2 1.726(5) .
O2 C16 1.302(4) .
N1 C7 1.286(5) .
N1 C8 1.459(5) .
O1 C1 1.313(5) .
N2 C10 1.278(5) .
N2 C9 1.470(5) .
C16 C11 1.426(5) .
C16 C15 1.416(6) .
C11 C10 1.436(5) .
C11 C12 1.408(5) .
C1 C6 1.411(6) .
C1 C2 1.420(5) .
C6 C7 1.442(5) .
C6 C5 1.403(5) .
C15 C14 1.364(5) .
C12 C13 1.364(6) .
C13 C14 1.386(6) .
C2 C3 1.381(6) .
C9 C8 1.506(6) .
C4 C3 1.352(7) .
C4 C5 1.377(6) .
