#------------------------------------------------------------------------------
#$Date: 2021-09-01 11:33:17 +0300 (Wed, 01 Sep 2021) $
#$Revision: 268348 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/45/1564508.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_1564508
loop_
_publ_author_name
'Santiago, Pedro H.O.'
'Santiago, Mariana B.'
'Martins, Carlos H.G.'
'Gatto, Claudia C.'
_publ_section_title
;
 Copper(II) and zinc(II) complexes with Hydrazone: Synthesis, crystal
 structure, Hirshfeld surface and antibacterial activity
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119632
_journal_paper_doi               10.1016/j.ica.2020.119632
_journal_volume                  508
_journal_year                    2020
_chemical_formula_moiety         'C13 H12 Cl2 Cu N4 O, 2(H2 O)'
_chemical_formula_sum            'C13 H16 Cl2 Cu N4 O3'
_chemical_formula_weight         410.74
_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   mixed
_atom_sites_solution_primary     direct
_cell_angle_alpha                94.723(3)
_cell_angle_beta                 96.994(3)
_cell_angle_gamma                118.855(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6985(11)
_cell_length_b                   8.7793(11)
_cell_length_c                   12.6496(16)
_cell_measurement_reflns_used    3482
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      21.69
_cell_measurement_theta_min      2.68
_cell_volume                     828.64(18)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19214
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.456
_diffrn_reflns_theta_min         1.644
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.658
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0955 before and 0.0564 after correction.
The Ratio of minimum to maximum transmission is 0.8582.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_description       Block
_exptl_crystal_F_000             418
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.137
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0017(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0353
_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)+(0.0368P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0827
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2381
_reflns_number_total             3079
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2020-508-119632.cif
_cod_data_source_block           ccg_phs_cu9_0m
_cod_database_code               1564508
_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   0.805
_shelx_estimated_absorpt_t_min   0.663
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O2(H2a,H2b), O3(H3a,H3b)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C10(H10), C4(H4a), C13(H13), C1(H1), C11(H11), C12(H12), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c)
;
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 0.60181(5) 0.52418(4) 0.28590(3) 0.03116(14) Uani 1 1 d . . . . .
Cl2 Cl 0.78205(11) 0.80747(10) 0.27668(7) 0.0431(2) Uani 1 1 d . . . . .
Cl1 Cl 0.73643(11) 0.36344(10) 0.18792(6) 0.0405(2) Uani 1 1 d . . . . .
O1 O 0.4047(3) 0.4740(3) 0.16302(17) 0.0369(5) Uani 1 1 d . . . . .
N3 N 0.2520(3) 0.2268(3) 0.24328(19) 0.0314(6) Uani 1 1 d . . . . .
N2 N 0.4073(3) 0.3122(3) 0.31822(18) 0.0285(6) Uani 1 1 d . . . . .
N1 N 0.7102(3) 0.5166(3) 0.43564(19) 0.0322(6) Uani 1 1 d . . . . .
C6 C 0.4282(4) 0.2521(4) 0.4047(2) 0.0301(7) Uani 1 1 d . . . . .
C5 C 0.6043(4) 0.3695(4) 0.4745(2) 0.0289(7) Uani 1 1 d . . . . .
C9 C 0.1048(4) 0.2559(4) 0.0822(2) 0.0287(7) Uani 1 1 d . . . . .
N4 N -0.2000(3) 0.0541(3) 0.0207(2) 0.0393(7) Uani 1 1 d . . . . .
H4 H -0.298275 -0.030900 0.031954 0.047 Uiso 1 1 calc R . . . .
C10 C -0.0545(4) 0.1192(4) 0.0971(2) 0.0334(7) Uani 1 1 d . . . . .
H10 H -0.060765 0.072195 0.160706 0.040 Uiso 1 1 calc R . . . .
C4 C 0.6590(5) 0.3366(4) 0.5729(3) 0.0404(8) Uani 1 1 d . . . . .
H4A H 0.585114 0.234888 0.598957 0.048 Uiso 1 1 calc R . . . .
C13 C 0.1068(4) 0.3191(4) -0.0140(3) 0.0434(9) Uani 1 1 d . . . . .
H13 H 0.212916 0.410206 -0.026966 0.052 Uiso 1 1 calc R . . . .
C1 C 0.8709(4) 0.6330(4) 0.4935(3) 0.0390(8) Uani 1 1 d . . . . .
H1 H 0.943270 0.734082 0.466386 0.047 Uiso 1 1 calc R . . . .
C7 C 0.2926(4) 0.0841(4) 0.4326(3) 0.0434(9) Uani 1 1 d . . . . .
H7A H 0.185682 0.033074 0.378853 0.065 Uiso 1 1 calc GR . . . .
H7B H 0.266253 0.106475 0.501766 0.065 Uiso 1 1 calc GR . . . .
H7C H 0.338211 0.004075 0.435118 0.065 Uiso 1 1 calc GR . . . .
C11 C -0.2001(4) 0.1146(4) -0.0723(3) 0.0440(9) Uani 1 1 d . . . . .
H11 H -0.304374 0.064989 -0.123794 0.053 Uiso 1 1 calc R . . . .
C12 C -0.0466(5) 0.2495(5) -0.0915(3) 0.0525(10) Uani 1 1 d . . . . .
H12 H -0.044658 0.294268 -0.155750 0.063 Uiso 1 1 calc R . . . .
C2 C 0.9328(5) 0.6072(5) 0.5928(3) 0.0467(9) Uani 1 1 d . . . . .
H2 H 1.044963 0.689834 0.632089 0.056 Uiso 1 1 calc R . . . .
O2 O 0.5507(4) 0.0109(4) 0.2912(3) 0.0797(9) Uani 1 1 d . . . . .
H2A H 0.590467 0.103770 0.262517 0.120 Uiso 1 1 d G . . . .
H2B H 0.617584 -0.031486 0.278842 0.120 Uiso 1 1 d G . . . .
C3 C 0.8257(5) 0.4579(5) 0.6319(3) 0.0480(9) Uani 1 1 d . . . . .
H3 H 0.865116 0.438098 0.698232 0.058 Uiso 1 1 calc R . . . .
C8 C 0.2669(4) 0.3264(4) 0.1677(2) 0.0291(7) Uani 1 1 d . . . . .
O3 O -0.5025(3) -0.2291(3) 0.0417(2) 0.0612(7) Uani 1 1 d . . . . .
H3A H -0.567890 -0.278927 -0.020218 0.092 Uiso 1 1 d G . . . .
H3B H -0.518893 -0.313642 0.075699 0.092 Uiso 1 1 d G . . . .
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
Cl2 Cu1 Cl1 103.90(3) . .
O1 Cu1 Cl2 97.99(6) . .
O1 Cu1 Cl1 97.12(7) . .
O1 Cu1 N1 156.44(9) . .
N2 Cu1 Cl2 161.26(8) . .
N2 Cu1 Cl1 94.84(7) . .
N2 Cu1 O1 79.25(9) . .
N2 Cu1 N1 79.29(10) . .
N1 Cu1 Cl2 99.21(7) . .
N1 Cu1 Cl1 94.24(7) . .
C8 O1 Cu1 108.69(18) . .
C8 N3 N2 107.9(2) . .
N3 N2 Cu1 117.37(17) . .
C6 N2 Cu1 120.3(2) . .
C6 N2 N3 122.2(2) . .
C5 N1 Cu1 112.89(19) . .
C1 N1 Cu1 127.6(2) . .
C1 N1 C5 119.4(3) . .
N2 C6 C5 112.4(2) . .
N2 C6 C7 124.4(3) . .
C5 C6 C7 123.2(3) . .
N1 C5 C6 114.7(2) . .
N1 C5 C4 121.4(3) . .
C4 C5 C6 123.9(3) . .
C10 C9 C13 117.4(3) . .
C10 C9 C8 119.7(3) . .
C13 C9 C8 122.8(3) . .
C11 N4 C10 122.9(3) . .
N4 C10 C9 120.2(3) . .
C5 C4 C3 118.6(3) . .
C9 C13 C12 121.0(3) . .
N1 C1 C2 121.8(3) . .
N4 C11 C12 119.5(3) . .
C11 C12 C13 118.9(3) . .
C3 C2 C1 118.7(3) . .
C2 C3 C4 120.1(3) . .
O1 C8 N3 126.2(3) . .
O1 C8 C9 119.0(3) . .
N3 C8 C9 114.7(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cl2 2.2330(8) .
Cu1 Cl1 2.5612(9) .
Cu1 O1 2.014(2) .
Cu1 N2 1.936(2) .
Cu1 N1 2.032(2) .
O1 C8 1.284(3) .
N3 N2 1.371(3) .
N3 C8 1.325(4) .
N2 C6 1.283(4) .
N1 C5 1.351(4) .
N1 C1 1.335(4) .
C6 C5 1.478(4) .
C6 C7 1.483(4) .
C5 C4 1.381(4) .
C9 C10 1.376(4) .
C9 C13 1.377(4) .
C9 C8 1.489(4) .
N4 C10 1.332(4) .
N4 C11 1.330(4) .
C4 C3 1.381(5) .
C13 C12 1.382(4) .
C1 C2 1.385(4) .
C11 C12 1.358(4) .
C2 C3 1.368(5) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4 O3 0.86 1.82 2.672(3) 172.2 . yes
O2 H2A Cl1 0.85 2.36 3.201(3) 172.7 . yes
O2 H2B Cl2 0.85 2.45 3.283(3) 166.7 1_545 yes
O3 H3A Cl1 0.85 2.27 3.106(2) 169.7 2 yes
O3 H3B O1 0.85 2.11 2.956(3) 171.6 1_445 yes
