#------------------------------------------------------------------------------
#$Date: 2019-12-18 08:31:17 +0200 (Wed, 18 Dec 2019) $
#$Revision: 245311 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/32/2243222.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243222
loop_
_publ_author_name
'Manawar, Rohit B.'
'Mamtora, Mayank J.'
'Shah, Manish K.'
'Jotani, Mukesh M.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and computational study of
 bis(2-{[(2,6-dichlorobenzylidene)hydrazinylidene]methyl}phenolato)cobalt(II)
 and of the copper(II) analogue
;
_journal_coeditor_code           HB7872
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              53
_journal_page_last               61
_journal_paper_doi               10.1107/S2056989019016529
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          '[Cu (C14 H9 Cl2 N2 O1)2]'
_chemical_formula_moiety         'C28 H18 Cl4 Cu N4 O2'
_chemical_formula_sum            'C28 H18 Cl4 Cu N4 O2'
_chemical_formula_weight         647.80
_chemical_name_systematic
;
Bis(2-{[(2,6-dichlorobenzylidene)hydrazinylidene]methyl}phenolato)copper(II)
;
_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
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                83.240(4)
_cell_angle_beta                 87.646(3)
_cell_angle_gamma                81.533(4)
_cell_formula_units_Z            1
_cell_length_a                   8.1300(7)
_cell_length_b                   8.5072(11)
_cell_length_c                   9.7386(13)
_cell_measurement_reflns_used    3126
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      56.529
_cell_measurement_theta_min      4.872
_cell_volume                     661.39(14)
_computing_cell_refinement
;
APEX2/SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2017/1 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare et al.,  1994)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_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            5554
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_min         3.254
_exptl_absorpt_coefficient_mu    1.265
_exptl_absorpt_correction_T_max  0.714
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            dark-brown
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_description       block
_exptl_crystal_F_000             327
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.456
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0326
_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)+(0.0461P)²+0.2934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0933
_reflns_number_gt                2708
_reflns_number_total             3090
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7872sup1.cif
_cod_data_source_block           II
_cod_database_code               2243222
_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   0.666
_shelx_estimated_absorpt_t_max   0.703
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Cu Cu 0.500000 0.500000 0.500000 0.02898(11) Uani d 1
Cl Cl1 0.31832(11) 0.73971(12) 0.01621(8) 0.0830(3) Uani d 1
Cl Cl2 -0.14142(7) 0.45455(7) 0.33048(7) 0.05364(17) Uani d 1
O O1 0.5954(2) 0.30738(17) 0.59863(16) 0.0435(4) Uani d 1
N N1 0.4436(2) 0.37945(19) 0.34549(16) 0.0293(3) Uani d 1
N N2 0.3392(2) 0.4457(2) 0.23415(17) 0.0352(4) Uani d 1
C C1 0.6593(3) 0.1736(2) 0.5513(2) 0.0338(4) Uani d 1
C C2 0.6301(3) 0.1364(2) 0.4182(2) 0.0325(4) Uani d 1
C C3 0.7051(3) -0.0117(3) 0.3762(3) 0.0439(5) Uani d 1
H H3 0.684470 -0.036821 0.288672 0.053 Uiso calc 1
C C4 0.8071(3) -0.1183(3) 0.4617(3) 0.0519(6) Uani d 1
H H4 0.857619 -0.214233 0.432071 0.062 Uiso calc 1
C C5 0.8345(3) -0.0824(3) 0.5923(3) 0.0519(6) Uani d 1
H H5 0.903270 -0.155502 0.650883 0.062 Uiso calc 1
C C6 0.7625(3) 0.0588(3) 0.6378(3) 0.0459(5) Uani d 1
H H6 0.782038 0.079204 0.726963 0.055 Uiso calc 1
C C7 0.5198(3) 0.2392(2) 0.3251(2) 0.0321(4) Uani d 1
H H7 0.500996 0.201827 0.242030 0.038 Uiso calc 1
C C8 0.2031(2) 0.5217(2) 0.2710(2) 0.0327(4) Uani d 1
H H8 0.179795 0.526076 0.364870 0.039 Uiso calc 1
C C9 0.0790(3) 0.6043(2) 0.1705(2) 0.0338(4) Uani d 1
C C10 0.1164(3) 0.7083(3) 0.0554(2) 0.0456(5) Uani d 1
C C11 -0.0074(4) 0.7920(3) -0.0292(3) 0.0597(7) Uani d 1
H H11 0.019998 0.861210 -0.105066 0.072 Uiso calc 1
C C12 -0.1692(4) 0.7730(3) -0.0015(3) 0.0676(9) Uani d 1
H H12 -0.251592 0.830675 -0.058269 0.081 Uiso calc 1
C C13 -0.2130(3) 0.6699(3) 0.1091(3) 0.0589(7) Uani d 1
H H13 -0.323355 0.655485 0.126954 0.071 Uiso calc 1
C C14 -0.0872(3) 0.5881(2) 0.1931(2) 0.0392(5) Uani d 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1 Cu O1 . 2_666 180.00(10)
O1 Cu N1 . . 90.28(6)
O1 Cu N1 2_666 . 89.72(6)
O1 Cu N1 . 2_666 89.72(6)
O1 Cu N1 2_666 2_666 90.28(6)
N1 Cu N1 . 2_666 180.0
C1 O1 Cu . . 128.77(13)
C7 N1 N2 . . 111.28(16)
C7 N1 Cu . . 123.02(13)
N2 N1 Cu . . 124.88(12)
C8 N2 N1 . . 113.85(16)
O1 C1 C6 . . 118.78(19)
O1 C1 C2 . . 123.59(18)
C6 C1 C2 . . 117.63(19)
C1 C2 C3 . . 119.48(19)
C1 C2 C7 . . 122.47(18)
C3 C2 C7 . . 117.97(19)
C4 C3 C2 . . 121.2(2)
C4 C3 H3 . . 119.4
C2 C3 H3 . . 119.4
C3 C4 C5 . . 119.3(2)
C3 C4 H4 . . 120.3
C5 C4 H4 . . 120.3
C6 C5 C4 . . 121.4(2)
C6 C5 H5 . . 119.3
C4 C5 H5 . . 119.3
C5 C6 C1 . . 121.0(2)
C5 C6 H6 . . 119.5
C1 C6 H6 . . 119.5
N1 C7 C2 . . 126.18(18)
N1 C7 H7 . . 116.9
C2 C7 H7 . . 116.9
N2 C8 C9 . . 122.34(18)
N2 C8 H8 . . 118.8
C9 C8 H8 . . 118.8
C14 C9 C10 . . 116.3(2)
C14 C9 C8 . . 119.63(19)
C10 C9 C8 . . 124.0(2)
C11 C10 C9 . . 121.3(3)
C11 C10 Cl1 . . 117.8(2)
C9 C10 Cl1 . . 120.87(18)
C12 C11 C10 . . 120.1(3)
C12 C11 H11 . . 120.0
C10 C11 H11 . . 120.0
C11 C12 C13 . . 121.1(2)
C11 C12 H12 . . 119.4
C13 C12 H12 . . 119.4
C14 C13 C12 . . 117.9(3)
C14 C13 H13 . . 121.1
C12 C13 H13 . . 121.1
C13 C14 C9 . . 123.3(2)
C13 C14 Cl2 . . 118.0(2)
C9 C14 Cl2 . . 118.66(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu O1 . 1.8776(14)
Cu O1 2_666 1.8776(14)
Cu N1 . 2.0211(16)
Cu N1 2_666 2.0211(16)
Cl1 C10 . 1.722(3)
Cl2 C14 . 1.737(2)
O1 C1 . 1.306(2)
N1 C7 . 1.294(2)
N1 N2 . 1.416(2)
N2 C8 . 1.258(3)
C1 C6 . 1.411(3)
C1 C2 . 1.407(3)
C2 C3 . 1.415(3)
C2 C7 . 1.428(3)
C3 C4 . 1.365(3)
C3 H3 . 0.9300
C4 C5 . 1.377(4)
C4 H4 . 0.9300
C5 C6 . 1.371(3)
C5 H5 . 0.9300
C6 H6 . 0.9300
C7 H7 . 0.9300
C8 C9 . 1.476(3)
C8 H8 . 0.9300
C9 C14 . 1.384(3)
C9 C10 . 1.396(3)
C10 C11 . 1.385(3)
C11 C12 . 1.361(5)
C11 H11 . 0.9300
C12 C13 . 1.376(5)
C12 H12 . 0.9300
C13 C14 . 1.387(3)
C13 H13 . 0.9300
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_site_symmetry_1
_geom_torsion
N1 Cu O1 C1 . 25.25(19)
N1 Cu O1 C1 2_666 -154.75(19)
C7 N1 N2 C8 . 141.33(19)
Cu N1 N2 C8 . -48.8(2)
Cu O1 C1 C6 . 163.39(17)
Cu O1 C1 C2 . -17.0(3)
O1 C1 C2 C3 . 179.9(2)
C6 C1 C2 C3 . -0.5(3)
O1 C1 C2 C7 . -3.5(3)
C6 C1 C2 C7 . 176.1(2)
C1 C2 C3 C4 . -0.9(3)
C7 C2 C3 C4 . -177.7(2)
C2 C3 C4 C5 . 1.4(4)
C3 C4 C5 C6 . -0.6(4)
C4 C5 C6 C1 . -0.9(4)
O1 C1 C6 C5 . -179.0(2)
C2 C1 C6 C5 . 1.4(4)
N2 N1 C7 C2 . -177.83(19)
Cu N1 C7 C2 . 12.1(3)
C1 C2 C7 N1 . 4.8(3)
C3 C2 C7 N1 . -178.5(2)
N1 N2 C8 C9 . 178.03(18)
N2 C8 C9 C14 . 134.7(2)
N2 C8 C9 C10 . -49.5(3)
C14 C9 C10 C11 . 1.1(3)
C8 C9 C10 C11 . -174.8(2)
C14 C9 C10 Cl1 . 179.69(17)
C8 C9 C10 Cl1 . 3.8(3)
C9 C10 C11 C12 . -0.4(4)
Cl1 C10 C11 C12 . -179.1(2)
C10 C11 C12 C13 . -0.8(4)
C11 C12 C13 C14 . 1.2(4)
C12 C13 C14 C9 . -0.5(4)
C12 C13 C14 Cl2 . -178.6(2)
C10 C9 C14 C13 . -0.6(3)
C8 C9 C14 C13 . 175.5(2)
C10 C9 C14 Cl2 . 177.47(16)
C8 C9 C14 Cl2 . -6.4(3)

_cod_database_fobs_code 2243222
