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#$Date: 2021-09-01 11:33:17 +0300 (Wed, 01 Sep 2021) $
#$Revision: 268348 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/45/1564509.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_1564509
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 Br2 Cu N4 O, 2(H2 O)'
_chemical_formula_sum            'C13 H16 Br2 Cu N4 O3'
_chemical_formula_weight         499.66
_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     dual
_cell_angle_alpha                95.985(2)
_cell_angle_beta                 97.046(2)
_cell_angle_gamma                119.341(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8985(11)
_cell_length_b                   8.9337(11)
_cell_length_c                   12.8937(16)
_cell_measurement_reflns_used    3651
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.70
_cell_measurement_theta_min      2.65
_cell_volume                     870.61(19)
_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    'ShelXT (Sheldrick, 2015)'
_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  0.0838
_diffrn_reflns_av_unetI/netI     0.0588
_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            20209
_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         25.491
_diffrn_reflns_theta_min         1.621
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.861
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1739 before and 0.0922 after correction.
The Ratio of minimum to maximum transmission is 0.6816.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_description       Block
_exptl_crystal_F_000             490
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.286
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.0013(5)
_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   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0338
_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)+(0.0178P)²+0.1596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0792
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2384
_reflns_number_total             3219
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2020-508-119632.cif
_cod_data_source_block           ccg_phs_cu10_0m
_cod_database_code               1564509
_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   0.285
_shelx_estimated_absorpt_t_min   0.197
_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
2. Restrained distances
3.a Free rotating group:
 H2A(O2,H2B,H3A,O3,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C10(H10), C1(H1), C4(H4A), C13(H13), C2(H2), C11(H11), C3(H3), C12(H12)
3.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
Br1 Br 1.23630(6) 0.35798(6) 0.18591(3) 0.04500(16) Uani 1 1 d . . . . .
Br2 Br 1.28917(6) 0.82034(6) 0.28504(4) 0.04849(16) Uani 1 1 d . . . . .
Cu1 Cu 1.09767(6) 0.52295(7) 0.29024(4) 0.03318(16) Uani 1 1 d . . . . .
O1 O 0.9041(3) 0.4729(4) 0.1687(2) 0.0371(7) Uani 1 1 d . . . . .
N1 N 1.2050(4) 0.5148(4) 0.4369(2) 0.0319(8) Uani 1 1 d . . . . .
N2 N 0.9054(4) 0.3129(4) 0.3182(2) 0.0304(8) Uani 1 1 d . . . . .
N3 N 0.7508(4) 0.2284(4) 0.2429(3) 0.0328(8) Uani 1 1 d . . . . .
N4 N 0.3067(4) 0.0534(5) 0.0230(3) 0.0414(9) Uani 1 1 d . . . . .
H4 H 0.210715 -0.032922 0.032684 0.050 Uiso 1 1 calc R . . . .
C8 C 0.7674(5) 0.3265(5) 0.1704(3) 0.0308(9) Uani 1 1 d . . . . .
C6 C 0.9255(5) 0.2510(5) 0.4009(3) 0.0322(10) Uani 1 1 d . . . . .
C5 C 1.0996(5) 0.3675(6) 0.4716(3) 0.0315(10) Uani 1 1 d . . . . .
C9 C 0.6074(5) 0.2573(5) 0.0861(3) 0.0317(10) Uani 1 1 d . . . . .
C10 C 0.4511(5) 0.1189(5) 0.0987(3) 0.0360(10) Uani 1 1 d . . . . .
H10 H 0.446389 0.071197 0.159844 0.043 Uiso 1 1 calc R . . . .
C1 C 1.3638(6) 0.6274(6) 0.4955(3) 0.0450(12) Uani 1 1 d . . . . .
H1 H 1.436728 0.728088 0.471212 0.054 Uiso 1 1 calc R . . . .
C4 C 1.1535(6) 0.3312(6) 0.5662(3) 0.0435(11) Uani 1 1 d . . . . .
H4A H 1.080147 0.229163 0.589117 0.052 Uiso 1 1 calc R . . . .
C13 C 0.6078(6) 0.3225(6) -0.0061(3) 0.0472(12) Uani 1 1 d . . . . .
H13 H 0.711594 0.414932 -0.017152 0.057 Uiso 1 1 calc R . . . .
C7 C 0.7898(6) 0.0832(5) 0.4256(3) 0.0446(12) Uani 1 1 d . . . . .
H7A H 0.686143 0.029727 0.370464 0.067 Uiso 1 1 calc GR . . . .
H7B H 0.760748 0.106041 0.492492 0.067 Uiso 1 1 calc GR . . . .
H7C H 0.835312 0.005773 0.429873 0.067 Uiso 1 1 calc GR . . . .
C2 C 1.4240(6) 0.5995(7) 0.5912(4) 0.0491(12) Uani 1 1 d . . . . .
H2 H 1.534643 0.681623 0.631492 0.059 Uiso 1 1 calc R . . . .
C11 C 0.3033(6) 0.1143(6) -0.0662(4) 0.0498(13) Uani 1 1 d . . . . .
H11 H 0.199495 0.064471 -0.116743 0.060 Uiso 1 1 calc R . . . .
C3 C 1.3198(6) 0.4509(7) 0.6258(4) 0.0527(13) Uani 1 1 d . . . . .
H3 H 1.359837 0.429362 0.689453 0.063 Uiso 1 1 calc R . . . .
C12 C 0.4550(6) 0.2516(7) -0.0827(4) 0.0565(14) Uani 1 1 d . . . . .
H12 H 0.455446 0.296772 -0.144491 0.068 Uiso 1 1 calc R . . . .
H2A H 1.111880 0.138998 0.277459 0.35(7) Uiso 1 1 d . . . . .
O2 O 1.0277(4) -0.0046(6) 0.2880(3) 0.1074(16) Uani 1 1 d G . . . .
H2B H 1.127969 0.002357 0.273998 0.40(8) Uiso 1 1 d G . . . .
H3A H -0.062401 -0.270940 -0.021058 0.094(19) Uiso 1 1 d G . . . .
O3 O 0.0123(4) -0.2305(5) 0.0475(3) 0.0843(13) Uani 1 1 d G . . . .
H3B H -0.014140 -0.312890 0.089442 0.19(4) 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'
Br Br -0.2901 2.4595 '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
Br2 Cu1 Br1 103.09(2) . .
O1 Cu1 Br1 97.22(8) . .
O1 Cu1 Br2 97.93(8) . .
O1 Cu1 N1 156.70(12) . .
N1 Cu1 Br1 93.88(9) . .
N1 Cu1 Br2 99.41(10) . .
N2 Cu1 Br1 95.23(10) . .
N2 Cu1 Br2 161.68(10) . .
N2 Cu1 O1 79.33(12) . .
N2 Cu1 N1 79.31(13) . .
C8 O1 Cu1 108.8(2) . .
C5 N1 Cu1 112.6(3) . .
C1 N1 Cu1 128.2(3) . .
C1 N1 C5 119.0(4) . .
N3 N2 Cu1 117.2(2) . .
C6 N2 Cu1 120.6(3) . .
C6 N2 N3 122.1(3) . .
C8 N3 N2 108.0(3) . .
C11 N4 C10 123.5(4) . .
O1 C8 N3 126.2(4) . .
O1 C8 C9 119.2(3) . .
N3 C8 C9 114.6(3) . .
N2 C6 C5 112.2(4) . .
N2 C6 C7 124.8(4) . .
C5 C6 C7 123.0(4) . .
N1 C5 C6 114.8(3) . .
N1 C5 C4 121.6(4) . .
C4 C5 C6 123.6(4) . .
C10 C9 C8 119.1(4) . .
C13 C9 C8 123.1(4) . .
C13 C9 C10 117.8(4) . .
N4 C10 C9 119.9(4) . .
N1 C1 C2 122.0(5) . .
C5 C4 C3 118.3(4) . .
C9 C13 C12 120.6(4) . .
C3 C2 C1 119.2(4) . .
N4 C11 C12 118.9(4) . .
C2 C3 C4 119.8(4) . .
C11 C12 C13 119.2(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 Cu1 2.6979(7) .
Br2 Cu1 2.3654(7) .
Cu1 O1 2.015(3) .
Cu1 N1 2.037(3) .
Cu1 N2 1.930(3) .
O1 C8 1.282(4) .
N1 C5 1.352(5) .
N1 C1 1.329(5) .
N2 N3 1.381(4) .
N2 C6 1.284(5) .
N3 C8 1.320(5) .
N4 C10 1.335(5) .
N4 C11 1.326(5) .
C8 C9 1.486(5) .
C6 C5 1.480(6) .
C6 C7 1.493(5) .
C5 C4 1.383(5) .
C9 C10 1.379(5) .
C9 C13 1.377(5) .
C1 C2 1.380(6) .
C4 C3 1.387(6) .
C13 C12 1.386(6) .
C2 C3 1.356(7) .
C11 C12 1.369(6) .
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 1.83 2.692(5) 174.7 . yes
O2 H2A Br1 1.16 2.264(11) 3.356(5) 156.0(18) . yes
O2 H2B Br2 0.91 2.65 3.382(4) 138.9 1_545 yes
O3 H3A Br1 0.95 2.28 3.230(3) 178.0 2_655 yes
O3 H3B O1 0.91 2.11 3.021(5) 172.7 1_445 yes
