#------------------------------------------------------------------------------
#$Date: 2021-11-24 11:39:48 +0200 (Wed, 24 Nov 2021) $
#$Revision: 270852 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/53/1565389.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_1565389
loop_
_publ_author_name
'Şahin, Musa'
'Eğlence-Bakır, Songül'
'Alpay, Merve'
'Alpay, Selin'
'Özmerdivenli, Recep'
'Ülküseven, Bahri'
_publ_section_title
;
 Effective copper(II) and nickel(II) complexes with N3O and ON3
 thiosemicarbazidato ligands. Synthesis, structural analysis and in vitro
 cytotoxity on melanoma B16F10 cells
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119347
_journal_paper_doi               10.1016/j.ica.2019.119347
_journal_volume                  502
_journal_year                    2020
_chemical_formula_moiety         'C18 H15 Br3 N4 Ni O S'
_chemical_formula_sum            'C18 H15 Br3 N4 Ni O S'
_chemical_formula_weight         633.84
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                107.93(2)
_cell_angle_beta                 101.94(2)
_cell_angle_gamma                93.81(2)
_cell_formula_units_Z            2
_cell_length_a                   7.082(6)
_cell_length_b                   12.394(10)
_cell_length_c                   13.144(10)
_cell_measurement_temperature    302(2)
_cell_volume                     1063.4(15)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      302(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1593
_diffrn_reflns_av_unetI/netI     0.4123
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6847
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.790
_exptl_absorpt_coefficient_mu    6.664
_exptl_crystal_density_diffrn    1.980
_exptl_crystal_F_000             616
_refine_diff_density_max         2.849
_refine_diff_density_min         -0.945
_refine_diff_density_rms         0.256
_refine_ls_extinction_coef       0.006(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3715
_refine_ls_number_restraints     268
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.3234
_refine_ls_R_factor_gt           0.1265
_refine_ls_shift/su_max          0.088
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1753P)²+8.3775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2879
_refine_ls_wR_factor_ref         0.3827
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1240
_reflns_number_total             3715
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1acif.cif
_cod_data_source_block           sm39_a
_cod_database_code               1565389
_shelx_shelxl_version_number     2014/7
_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.
;
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 0.7061(4) 0.1813(3) 0.8423(3) 0.0606(12) Uani 1 1 d . . . . .
Ni Ni 0.2405(4) 0.4979(3) 0.4892(2) 0.0302(10) Uani 1 1 d . . . . .
Br3 Br -0.2837(5) 0.6637(3) 0.0291(2) 0.0649(12) Uani 1 1 d . . . . .
Br2 Br 0.2188(6) 0.0843(3) 0.4181(3) 0.0805(14) Uani 1 1 d . . . . .
S S 0.5118(14) 0.7668(8) 0.8023(6) 0.076(3) Uani 1 1 d . . . . .
O1 O 0.108(2) 0.4320(15) 0.3421(13) 0.041(5) Uani 1 1 d . . . . .
N2 N 0.302(3) 0.7334(17) 0.6009(16) 0.031(4) Uani 1 1 d . U . . .
N1 N 0.373(3) 0.5666(18) 0.6362(14) 0.050(10) Uani 1.04(6) 1 d . U . . .
N3 N 0.208(3) 0.6501(16) 0.4983(15) 0.029(4) Uani 1 1 d . U . . .
C5 C 0.109(3) 0.683(2) 0.4199(19) 0.034(4) Uani 1 1 d . U . . .
H7 H 0.0965 0.7604 0.4366 0.041 Uiso 1 1 calc R U . . .
N4 N 0.270(3) 0.3509(18) 0.4885(17) 0.042(6) Uani 1 1 d . U . . .
H4 H 0.2175 0.2979 0.4270 0.051 Uiso 1 1 calc R U . . .
C8 C 0.031(4) 0.491(2) 0.282(2) 0.036(3) Uani 1 1 d . U . . .
C13 C 0.461(3) 0.392(2) 0.674(2) 0.038(3) Uani 1 1 d . U . . .
C14 C 0.567(3) 0.354(2) 0.758(2) 0.039(3) Uani 1 1 d . U . . .
H8 H 0.6343 0.4071 0.8248 0.047 Uiso 1 1 calc R U . . .
C18 C 0.570(4) 0.234(2) 0.739(2) 0.041(3) Uani 1 1 d . U . . .
C6 C 0.021(3) 0.611(2) 0.314(2) 0.035(3) Uani 1 1 d . U . . .
C7 C -0.065(3) 0.662(2) 0.238(2) 0.037(3) Uani 1 1 d . U . . .
H6 H -0.0587 0.7413 0.2600 0.044 Uiso 1 1 calc R U . . .
C12 C 0.466(3) 0.509(2) 0.702(2) 0.037(4) Uani 1 1 d . U . . .
H2 H 0.5389 0.5535 0.7714 0.044 Uiso 1 1 calc R U . . .
C4 C 0.387(4) 0.684(2) 0.667(2) 0.037(7) Uani 1 1 d . U . . .
C9 C -0.065(3) 0.424(2) 0.168(2) 0.040(3) Uani 1 1 d . U . . .
H3 H -0.0644 0.3457 0.1420 0.048 Uiso 1 1 calc R U . . .
C16 C 0.356(4) 0.196(2) 0.553(2) 0.040(4) Uani 1 1 d . U . . .
C15 C 0.358(4) 0.315(2) 0.566(2) 0.039(3) Uani 1 1 d . U . . .
C11 C -0.161(3) 0.480(2) 0.096(2) 0.042(4) Uani 1 1 d . U . . .
H9 H -0.2269 0.4372 0.0239 0.050 Uiso 1 1 calc R U . . .
C10 C -0.158(4) 0.599(2) 0.132(2) 0.040(3) Uani 1 1 d . U . . .
C17 C 0.448(3) 0.156(2) 0.635(2) 0.042(4) Uani 1 1 d . U . . .
H10 H 0.4323 0.0778 0.6234 0.051 Uiso 1 1 calc R U . . .
C3 C 0.398(6) 0.895(3) 0.818(4) 0.118(10) Uani 1 1 d . U . . .
H1A H 0.4814 0.9548 0.8814 0.142 Uiso 1 1 calc R U . . .
H1B H 0.4030 0.9180 0.7543 0.142 Uiso 1 1 calc R U . . .
C2 C 0.209(6) 0.899(3) 0.831(4) 0.119(10) Uani 1 1 d . U . . .
H2A H 0.1211 0.8457 0.7656 0.143 Uiso 1 1 calc R U . . .
H2B H 0.1983 0.8724 0.8924 0.143 Uiso 1 1 calc R U . . .
C1 C 0.145(6) 1.006(3) 0.851(3) 0.127(10) Uani 1 1 d . U . . .
H4A H 0.2518 1.0633 0.8609 0.190 Uiso 1 1 calc R U . . .
H4B H 0.0956 1.0246 0.9161 0.190 Uiso 1 1 calc R U . . .
H4C H 0.0433 1.0046 0.7892 0.190 Uiso 1 1 calc R U . . .
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'
N N 0.0061 0.0033 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
N1 Ni N4 94.5(9) . .
N1 Ni O1 178.9(9) . .
N4 Ni O1 86.6(9) . .
N1 Ni N3 82.9(8) . .
N4 Ni N3 176.6(8) . .
O1 Ni N3 96.0(8) . .
C4 S C3 100.4(17) . .
C8 O1 Ni 123.2(17) . .
C4 N2 N3 110.0(19) . .
C12 N1 C4 124(2) . .
C12 N1 Ni 124.5(18) . .
C4 N1 Ni 111.3(16) . .
C5 N3 N2 119(2) . .
C5 N3 Ni 126.0(17) . .
N2 N3 Ni 114.6(13) . .
N3 C5 C6 125(2) . .
N3 C5 H7 117.6 . .
C6 C5 H7 117.6 . .
C15 N4 Ni 130(2) . .
C15 N4 H4 115.0 . .
Ni N4 H4 115.0 . .
O1 C8 C6 129(2) . .
O1 C8 C9 115(2) . .
C6 C8 C9 116(2) . .
C12 C13 C14 115(2) . .
C12 C13 C15 121(2) . .
C14 C13 C15 124(3) . .
C18 C14 C13 120(2) . .
C18 C14 H8 120.1 . .
C13 C14 H8 120.1 . .
C14 C18 C17 117(2) . .
C14 C18 Br1 121.7(19) . .
C17 C18 Br1 121(2) . .
C7 C6 C5 117(2) . .
C7 C6 C8 122(2) . .
C5 C6 C8 121(2) . .
C10 C7 C6 122(3) . .
C10 C7 H6 119.0 . .
C6 C7 H6 119.0 . .
N1 C12 C13 126(2) . .
N1 C12 H2 116.7 . .
C13 C12 H2 116.8 . .
N2 C4 N1 121(2) . .
N2 C4 S 120.1(19) . .
N1 C4 S 119(2) . .
C11 C9 C8 120(3) . .
C11 C9 H3 120.0 . .
C8 C9 H3 120.0 . .
C17 C16 C15 123(3) . .
C17 C16 Br2 117(2) . .
C15 C16 Br2 119.9(19) . .
N4 C15 C16 122(2) . .
N4 C15 C13 123(3) . .
C16 C15 C13 115(2) . .
C9 C11 C10 121(3) . .
C9 C11 H9 119.7 . .
C10 C11 H9 119.7 . .
C7 C10 C11 120(2) . .
C7 C10 Br3 123(2) . .
C11 C10 Br3 116.8(19) . .
C16 C17 C18 121(3) . .
C16 C17 H10 119.4 . .
C18 C17 H10 119.4 . .
C2 C3 S 122(3) . .
C2 C3 H1A 106.8 . .
S C3 H1A 106.8 . .
C2 C3 H1B 106.8 . .
S C3 H1B 106.8 . .
H1A C3 H1B 106.7 . .
C1 C2 C3 116(4) . .
C1 C2 H2A 108.4 . .
C3 C2 H2A 108.3 . .
C1 C2 H2B 108.4 . .
C3 C2 H2B 108.4 . .
H2A C2 H2B 107.4 . .
C2 C1 H4A 109.5 . .
C2 C1 H4B 109.5 . .
H4A C1 H4B 109.5 . .
C2 C1 H4C 109.5 . .
H4A C1 H4C 109.5 . .
H4B C1 H4C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C18 1.82(3) .
Ni N1 1.863(18) .
Ni N4 1.84(2) .
Ni O1 1.859(16) .
Ni N3 1.887(18) .
Br3 C10 1.88(3) .
Br2 C16 1.89(3) .
S C4 1.76(3) .
S C3 1.81(3) .
O1 C8 1.30(3) .
N2 C4 1.28(3) .
N2 N3 1.42(3) .
N1 C12 1.37(3) .
N1 C4 1.38(3) .
N3 C5 1.31(3) .
C5 C6 1.39(3) .
C5 H7 0.9300 .
N4 C15 1.30(3) .
N4 H4 0.8600 .
C8 C6 1.42(4) .
C8 C9 1.46(3) .
C13 C12 1.38(3) .
C13 C14 1.41(3) .
C13 C15 1.45(3) .
C14 C18 1.43(3) .
C14 H8 0.9300 .
C18 C17 1.46(3) .
C6 C7 1.40(3) .
C7 C10 1.36(3) .
C7 H6 0.9300 .
C12 H2 0.9300 .
C9 C11 1.43(3) .
C9 H3 0.9300 .
C16 C17 1.38(3) .
C16 C15 1.43(3) .
C11 C10 1.40(4) .
C11 H9 0.9300 .
C17 H10 0.9300 .
C3 C2 1.39(5) .
C3 H1A 0.9700 .
C3 H1B 0.9700 .
C2 C1 1.40(5) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C1 H4A 0.9600 .
C1 H4B 0.9600 .
C1 H4C 0.9600 .
