#------------------------------------------------------------------------------
#$Date: 2022-01-15 04:38:26 +0200 (Sat, 15 Jan 2022) $
#$Revision: 272055 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/40/2244014.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_2244014
loop_
_publ_author_name
'Vassilyeva, Olga Yu.'
'Buvaylo, Elena A.'
'Kokozay, Vladimir N.'
'Studzinsky, Sergey L.'
'Skelton, Brian W.'
'Vasyliev, Georgii S.'
_publ_section_title
;
 NiII molecular complex with a tetradentate aminoguanidine-derived
 Schiff base ligand: structural, spectroscopic and electrochemical studies
 and photoelectric response
;
_journal_coeditor_code           DJ2041
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022000317
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          '[Ni (C15 H11 Br N4 O2)], C3 H7 N O, H2 O'
_chemical_formula_moiety         'C15 H11 Br N4 Ni O2, C3 H7 N O, H2 O'
_chemical_formula_sum            'C18 H20 Br N5 Ni O4'
_chemical_formula_weight         509.01
_chemical_name_systematic
;{4-Bromo-2-[({N'-[(2-oxidobenzylidene)amino]carbamimidoyl}imino)methyl]phenolato}nickel(II)
N,N-dimethylformamide monosolvate monohydrate
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                95.338(4)
_cell_angle_beta                 104.493(4)
_cell_angle_gamma                112.592(5)
_cell_formula_units_Z            2
_cell_length_a                   8.3057(4)
_cell_length_b                   9.2300(4)
_cell_length_c                   14.3970(7)
_cell_measurement_reflns_used    11025
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.2605
_cell_measurement_theta_min      3.3928
_cell_volume                     964.23(9)
_computing_cell_refinement
;
CrysAlis Pro (Rigaku OD, 2016)
;
_computing_data_collection
;
CrysAlis Pro (Rigaku OD, 2016)
;
_computing_data_reduction
;
CrysAlis Pro (Rigaku OD, 2016)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.0009
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0919
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28563
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.5
_diffrn_reflns_theta_min         3.4
_exptl_absorpt_coefficient_mu    3.115
_exptl_absorpt_correction_T_max  0.721
_exptl_absorpt_correction_T_min  0.484
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlis Pro; Rigaku OD, 2016)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_description       plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.73
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         9442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0353P)²+0.1785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.078
_refine_ls_wR_factor_ref         0.0826
_reflns_number_gt                7711
_reflns_number_total             9442
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dj2041sup1.cif
_cod_data_source_block           I
_cod_database_code               2244014
loop_
_symmetry_equiv_pos_as_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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni1 0.71284(2) 0.50588(2) 0.54926(2) 0.01171(4) Uani d 1 . .
Br Br1 0.78673(2) -0.02916(2) 0.16762(2) 0.02100(4) Uani d 1 . .
C C11 0.59223(17) 0.53634(16) 0.71522(10) 0.0144(2) Uani d 1 . .
O O11 0.61079(14) 0.44311(12) 0.64783(8) 0.01633(18) Uani d 1 . .
C C12 0.65390(17) 0.70528(16) 0.72467(10) 0.0145(2) Uani d 1 . .
C C13 0.62837(19) 0.79600(18) 0.79975(11) 0.0183(3) Uani d 1 . .
H H13 0.670747 0.908793 0.805476 0.022 Uiso calc 1 . .
C C14 0.5434(2) 0.72456(19) 0.86487(11) 0.0203(3) Uani d 1 . .
H H14 0.528595 0.787163 0.915561 0.024 Uiso calc 1 . .
C C15 0.4794(2) 0.55819(19) 0.85484(11) 0.0205(3) Uani d 1 . .
H H15 0.418098 0.507219 0.898316 0.025 Uiso calc 1 . .
C C16 0.5039(2) 0.46680(18) 0.78260(11) 0.0182(3) Uani d 1 . .
H H16 0.460325 0.354169 0.778076 0.022 Uiso calc 1 . .
C C1 0.73956(18) 0.78904(17) 0.65882(10) 0.0150(2) Uani d 1 . .
H H1 0.776971 0.901853 0.668905 0.018 Uiso calc 1 . .
N N2 0.76894(15) 0.71997(13) 0.58640(9) 0.01352(19) Uani d 1 . .
N N3 0.85703(16) 0.82274(14) 0.53203(9) 0.0156(2) Uani d 1 . .
C C4 0.88158(18) 0.74226(16) 0.46136(10) 0.0142(2) Uani d 1 . .
N N4 0.96020(18) 0.81776(15) 0.39828(10) 0.0179(2) Uani d 1 . .
N N5 0.81845(15) 0.57454(13) 0.45334(8) 0.01256(19) Uani d 1 . .
C C6 0.83447(17) 0.48570(16) 0.38291(10) 0.0134(2) Uani d 1 . .
H H6 0.887782 0.537164 0.336972 0.016 Uiso calc 1 . .
C C21 0.69562(17) 0.22941(16) 0.43607(10) 0.0135(2) Uani d 1 . .
O O21 0.66497(14) 0.29247(12) 0.51103(8) 0.01554(18) Uani d 1 . .
C C22 0.77713(17) 0.31744(15) 0.37102(10) 0.0129(2) Uani d 1 . .
C C23 0.80347(18) 0.23840(16) 0.29043(10) 0.0145(2) Uani d 1 . .
H H23 0.85787 0.297919 0.247395 0.017 Uiso calc 1 . .
C C24 0.75004(18) 0.07631(17) 0.27528(11) 0.0158(2) Uani d 1 . .
C C25 0.67098(19) -0.01344(17) 0.33888(11) 0.0175(2) Uani d 1 . .
H H25 0.635444 -0.126036 0.327557 0.021 Uiso calc 1 . .
C C26 0.64509(19) 0.06105(16) 0.41707(11) 0.0168(2) Uani d 1 . .
H H26 0.592223 -0.001036 0.459596 0.02 Uiso calc 1 . .
C C101 1.2835(2) 0.7674(2) 1.04820(14) 0.0279(3) Uani d 1 . .
H H10A 1.320626 0.688278 1.021153 0.042 Uiso calc 1 . .
H H10B 1.303048 0.771121 1.118552 0.042 Uiso calc 1 . .
H H10C 1.356958 0.873448 1.038389 0.042 Uiso calc 1 . .
C C102 1.0013(2) 0.8037(2) 1.04333(14) 0.0300(4) Uani d 1 . .
H H10D 1.008633 0.783988 1.109651 0.045 Uiso calc 1 . .
H H10E 0.872272 0.762924 1.00362 0.045 Uiso calc 1 . .
H H10F 1.062839 0.91934 1.0469 0.045 Uiso calc 1 . .
N N10 1.09055(17) 0.72197(16) 0.99855(10) 0.0211(2) Uani d 1 . .
C C10 0.9998(2) 0.6113(2) 0.91592(12) 0.0240(3) Uani d 1 . .
H H10 0.873871 0.587458 0.88718 0.029 Uiso calc 1 . .
O O10 1.06542(18) 0.53699(16) 0.87336(9) 0.0302(3) Uani d 1 . .
O O1 0.8463(2) 0.27288(17) 0.72054(11) 0.0263(2) Uani d 1 . .
H H4A 1.011(3) 0.919(3) 0.4152(17) 0.032(6) Uiso d 1 . .
H H4B 1.005(3) 0.780(3) 0.3645(18) 0.036(6) Uiso d 1 . .
H H1A 0.773(4) 0.281(3) 0.686(2) 0.054(9) Uiso d 1 . .
H H1B 0.911(4) 0.349(3) 0.764(2) 0.044(7) Uiso 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 0 '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 0.006 '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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0564
0 0 -1 0.0588
3 0 -2 0.1271
0 1 -1 0.0853
-2 1 1 0.1747
-2 0 1 0.1246
1 -3 -1 0.1273
-1 -2 0 0.0985
3 -2 -2 0.1308
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
_geom_angle_publ_flag
N2 Ni1 N5 . . 83.08(5) y
N2 Ni1 O21 . . 177.80(5) y
N5 Ni1 O21 . . 95.25(5) y
N2 Ni1 O11 . . 95.35(5) y
N5 Ni1 O11 . . 178.29(5) y
O21 Ni1 O11 . . 86.30(4) y
O11 C11 C16 . . 119.03(13) ?
O11 C11 C12 . . 124.05(12) ?
C16 C11 C12 . . 116.91(12) ?
C11 O11 Ni1 . . 126.59(9) ?
C13 C12 C11 . . 120.07(13) ?
C13 C12 C1 . . 117.68(13) ?
C11 C12 C1 . . 122.24(12) ?
C14 C13 C12 . . 121.51(14) ?
C14 C13 H13 . . 119.2 ?
C12 C13 H13 . . 119.2 ?
C13 C14 C15 . . 118.70(14) ?
C13 C14 H14 . . 120.7 ?
C15 C14 H14 . . 120.7 ?
C16 C15 C14 . . 120.97(14) ?
C16 C15 H15 . . 119.5 ?
C14 C15 H15 . . 119.5 ?
C15 C16 C11 . . 121.82(14) ?
C15 C16 H16 . . 119.1 ?
C11 C16 H16 . . 119.1 ?
N2 C1 C12 . . 123.84(13) ?
N2 C1 H1 . . 118.1 ?
C12 C1 H1 . . 118.1 ?
C1 N2 N3 . . 115.09(12) ?
C1 N2 Ni1 . . 127.91(10) ?
N3 N2 Ni1 . . 116.98(9) ?
C4 N3 N2 . . 110.50(11) ?
N3 C4 N4 . . 120.38(12) ?
N3 C4 N5 . . 117.40(12) ?
N4 C4 N5 . . 122.21(12) ?
C4 N4 H4A . . 114.7(15) ?
C4 N4 H4B . . 123.3(17) ?
H4A N4 H4B . . 115(2) ?
C6 N5 C4 . . 120.76(12) ?
C6 N5 Ni1 . . 127.20(9) ?
C4 N5 Ni1 . . 112.02(9) ?
N5 C6 C22 . . 124.01(12) ?
N5 C6 H6 . . 118 ?
C22 C6 H6 . . 118 ?
O21 C21 C26 . . 118.42(12) ?
O21 C21 C22 . . 124.57(12) ?
C26 C21 C22 . . 117.02(12) ?
C21 O21 Ni1 . . 126.68(9) ?
C6 C22 C23 . . 117.06(12) ?
C6 C22 C21 . . 122.19(12) ?
C23 C22 C21 . . 120.75(12) ?
C24 C23 C22 . . 119.52(13) ?
C24 C23 H23 . . 120.2 ?
C22 C23 H23 . . 120.2 ?
C23 C24 C25 . . 120.99(13) ?
C23 C24 Br1 . . 119.43(11) ?
C25 C24 Br1 . . 119.57(10) ?
C26 C25 C24 . . 120.21(13) ?
C26 C25 H25 . . 119.9 ?
C24 C25 H25 . . 119.9 ?
C25 C26 C21 . . 121.51(13) ?
C25 C26 H26 . . 119.2 ?
C21 C26 H26 . . 119.2 ?
N10 C101 H10A . . 109.5 ?
N10 C101 H10B . . 109.5 ?
H10A C101 H10B . . 109.5 ?
N10 C101 H10C . . 109.5 ?
H10A C101 H10C . . 109.5 ?
H10B C101 H10C . . 109.5 ?
N10 C102 H10D . . 109.5 ?
N10 C102 H10E . . 109.5 ?
H10D C102 H10E . . 109.5 ?
N10 C102 H10F . . 109.5 ?
H10D C102 H10F . . 109.5 ?
H10E C102 H10F . . 109.5 ?
C10 N10 C101 . . 121.63(14) ?
C10 N10 C102 . . 121.41(14) ?
C101 N10 C102 . . 116.96(14) ?
O10 C10 N10 . . 125.34(16) ?
O10 C10 H10 . . 117.3 ?
N10 C10 H10 . . 117.3 ?
H1A O1 H1B . . 115(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 N2 . 1.8383(11) y
Ni1 N5 . 1.8494(11) y
Ni1 O21 . 1.8515(10) y
Ni1 O11 . 1.8562(10) y
Br1 C24 . 1.9044(14) ?
C11 O11 . 1.3142(17) ?
C11 C16 . 1.415(2) ?
C11 C12 . 1.4228(19) ?
C12 C13 . 1.413(2) ?
C12 C1 . 1.433(2) ?
C13 C14 . 1.379(2) ?
C13 H13 . 0.95 ?
C14 C15 . 1.398(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.382(2) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C1 N2 . 1.2947(18) ?
C1 H1 . 0.95 ?
N2 N3 . 1.3926(16) ?
N3 C4 . 1.3069(18) ?
C4 N4 . 1.3423(18) ?
C4 N5 . 1.4133(17) ?
N4 H4A . 0.85(2) ?
N4 H4B . 0.81(2) ?
N5 C6 . 1.3095(17) ?
C6 C22 . 1.4176(18) ?
C6 H6 . 0.95 ?
C21 O21 . 1.3048(16) ?
C21 C26 . 1.4241(19) ?
C21 C22 . 1.4255(19) ?
C22 C23 . 1.4208(19) ?
C23 C24 . 1.3651(19) ?
C23 H23 . 0.95 ?
C24 C25 . 1.407(2) ?
C25 C26 . 1.370(2) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
C101 N10 . 1.452(2) ?
C101 H10A . 0.98 ?
C101 H10B . 0.98 ?
C101 H10C . 0.98 ?
C102 N10 . 1.453(2) ?
C102 H10D . 0.98 ?
C102 H10E . 0.98 ?
C102 H10F . 0.98 ?
N10 C10 . 1.327(2) ?
C10 O10 . 1.233(2) ?
C10 H10 . 0.95 ?
O1 H1A . 0.72(3) ?
O1 H1B . 0.80(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N4 H4A N3 2_776 0.85(2) 2.16(2) 3.0116(17) 176(2) yes
N4 H4B O1 2_766 0.81(2) 2.09(2) 2.8900(19) 169(2) yes
O1 H1A O11 . 0.72(3) 2.38(3) 3.0056(17) 146(3) yes
O1 H1A O21 . 0.72(3) 2.48(3) 3.0719(18) 141(3) yes
O1 H1B O10 . 0.80(3) 1.97(3) 2.772(2) 178(3) yes
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C16 C11 O11 Ni1 . . . . 177.39(10) ?
C12 C11 O11 Ni1 . . . . -1.81(19) ?
N2 Ni1 O11 C11 . . . . 1.06(12) ?
O21 Ni1 O11 C11 . . . . 179.59(11) ?
O11 C11 C12 C13 . . . . -179.83(13) ?
C16 C11 C12 C13 . . . . 0.96(19) ?
O11 C11 C12 C1 . . . . 1.4(2) ?
C16 C11 C12 C1 . . . . -177.81(13) ?
C11 C12 C13 C14 . . . . -0.3(2) ?
C1 C12 C13 C14 . . . . 178.49(13) ?
C12 C13 C14 C15 . . . . -0.9(2) ?
C13 C14 C15 C16 . . . . 1.4(2) ?
C14 C15 C16 C11 . . . . -0.8(2) ?
O11 C11 C16 C15 . . . . -179.68(13) ?
C12 C11 C16 C15 . . . . -0.4(2) ?
C13 C12 C1 N2 . . . . -179.16(13) ?
C11 C12 C1 N2 . . . . -0.4(2) ?
C12 C1 N2 N3 . . . . -178.84(12) ?
C12 C1 N2 Ni1 . . . . -0.2(2) ?
N5 Ni1 N2 C1 . . . . -179.40(13) ?
O11 Ni1 N2 C1 . . . . -0.08(13) ?
N5 Ni1 N2 N3 . . . . -0.76(9) ?
O11 Ni1 N2 N3 . . . . 178.56(9) ?
C1 N2 N3 C4 . . . . 179.55(12) ?
Ni1 N2 N3 C4 . . . . 0.73(14) ?
N2 N3 C4 N4 . . . . 178.31(12) ?
N2 N3 C4 N5 . . . . -0.22(17) ?
N3 C4 N5 C6 . . . . 178.37(12) ?
N4 C4 N5 C6 . . . . -0.1(2) ?
N3 C4 N5 Ni1 . . . . -0.36(15) ?
N4 C4 N5 Ni1 . . . . -178.86(11) ?
N2 Ni1 N5 C6 . . . . -178.04(12) ?
O21 Ni1 N5 C6 . . . . 3.41(12) ?
N2 Ni1 N5 C4 . . . . 0.59(9) ?
O21 Ni1 N5 C4 . . . . -177.96(9) ?
C4 N5 C6 C22 . . . . 178.98(12) ?
Ni1 N5 C6 C22 . . . . -2.50(19) ?
C26 C21 O21 Ni1 . . . . -178.48(9) ?
C22 C21 O21 Ni1 . . . . 1.61(19) ?
N5 Ni1 O21 C21 . . . . -2.96(11) ?
O11 Ni1 O21 C21 . . . . 177.76(11) ?
N5 C6 C22 C23 . . . . 179.74(12) ?
N5 C6 C22 C21 . . . . 0.0(2) ?
O21 C21 C22 C6 . . . . 0.4(2) ?
C26 C21 C22 C6 . . . . -179.48(12) ?
O21 C21 C22 C23 . . . . -179.27(13) ?
C26 C21 C22 C23 . . . . 0.82(18) ?
C6 C22 C23 C24 . . . . -179.73(12) ?
C21 C22 C23 C24 . . . . -0.02(19) ?
C22 C23 C24 C25 . . . . -0.7(2) ?
C22 C23 C24 Br1 . . . . -179.66(10) ?
C23 C24 C25 C26 . . . . 0.5(2) ?
Br1 C24 C25 C26 . . . . 179.49(11) ?
C24 C25 C26 C21 . . . . 0.4(2) ?
O21 C21 C26 C25 . . . . 179.09(13) ?
C22 C21 C26 C25 . . . . -1.0(2) ?
C101 N10 C10 O10 . . . . 0.1(3) ?
C102 N10 C10 O10 . . . . 179.88(17) ?

_cod_database_fobs_code 2244014
