#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/67/2236763.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_2236763
loop_
_publ_author_name
'Pederzolli, Fernanda Rosi Soares'
'Bresolin, Leandro'
'Beck, Johannes'
'Daniels, Jörg'
'de Oliveira, Adriano Bof'
_publ_section_title
;
 [1-(5-Bromo-2-oxidobenzylidene)thiosemicarbazidato-κ³O,N¹,S](pyridine-κN)nickel(II)
;
_journal_coeditor_code           ZL2486
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1138
_journal_paper_doi               10.1107/S1600536812028917
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Ni (C8 H6 Br N3 O S) (C5 H5 N)]'
_chemical_formula_moiety         'C13 H11 Br N4 Ni O S'
_chemical_formula_sum            'C13 H11 Br N4 Ni O S'
_chemical_formula_weight         409.94
_chemical_name_systematic
;
[1-(5-Bromo-2-oxidobenzylidene)thiosemicarbazidato-
κ³O,N¹,S](pyridine-κN)nickel(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 112.6460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2447(4)
_cell_length_b                   4.11350(10)
_cell_length_c                   31.1380(11)
_cell_measurement_reflns_used    17227
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.91
_cell_volume                     1447.46(8)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            13946
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    4.247
_exptl_absorpt_correction_T_max  0.8303
_exptl_absorpt_correction_T_min  0.4429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Blessing, 1995)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.928
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.663
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0442P)²+0.6555P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0831
_reflns_number_gt                2697
_reflns_number_total             3224
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zl2486.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236763
_cod_database_fobs_code          2236763
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_refinement_flags
_atom_site_occupancy
Br Br1 1.37247(2) 0.72025(7) 0.228104(10) 0.04622(11) Uani d . 1
Ni Ni1 0.80812(3) -0.06339(9) 0.089703(11) 0.03527(11) Uani d . 1
S S1 0.71884(6) -0.35252(19) 0.02859(2) 0.04380(17) Uani d . 1
O O1 0.87955(16) 0.1736(5) 0.14418(7) 0.0419(4) Uani d . 1
N N1 0.93997(18) -0.0757(5) 0.07408(7) 0.0339(4) Uani d . 1
N N2 0.9399(2) -0.2507(6) 0.03540(8) 0.0403(5) Uani d . 1
N N3 0.8245(2) -0.5541(7) -0.02746(9) 0.0519(6) Uani d . 1
H H1 0.8831 -0.6069 -0.03 0.062 Uiso d R 1
H H2 0.7769 -0.6986 -0.0334 0.062 Uiso d R 1
N N4 0.67067(19) -0.0743(6) 0.10494(8) 0.0383(5) Uani d . 1
C C1 1.0684(2) 0.2490(6) 0.13889(9) 0.0350(5) Uani d . 1
C C2 0.9877(2) 0.2887(6) 0.16117(9) 0.0357(5) Uani d . 1
C C3 1.0269(2) 0.4575(7) 0.20359(10) 0.0423(6) Uani d . 1
H H3 0.9751 0.4858 0.2187 0.051 Uiso calc R 1
C C4 1.1399(2) 0.5829(7) 0.22359(10) 0.0428(6) Uani d . 1
H H4 1.1642 0.6923 0.2519 0.051 Uiso calc R 1
C C5 1.2167(2) 0.5430(6) 0.20077(9) 0.0377(5) Uani d . 1
C C6 1.1830(2) 0.3830(7) 0.15955(10) 0.0377(5) Uani d . 1
H H6 1.2358 0.3616 0.1448 0.045 Uiso calc R 1
C C7 1.0394(2) 0.0704(7) 0.09658(9) 0.0380(6) Uani d . 1
H H7 1.0971 0.0579 0.0841 0.046 Uiso calc R 1
C C8 0.8393(2) -0.3869(7) 0.01258(9) 0.0390(6) Uani d . 1
C C9 0.5660(2) 0.0532(7) 0.07772(10) 0.0439(6) Uani d . 1
H H9 0.558 0.1437 0.0493 0.053 Uiso calc R 1
C C10 0.4699(3) 0.0547(9) 0.09040(12) 0.0553(8) Uani d . 1
H H10 0.3986 0.1475 0.0711 0.066 Uiso calc R 1
C C11 0.4810(3) -0.0826(9) 0.13187(12) 0.0586(8) Uani d . 1
H H11 0.4172 -0.0845 0.1411 0.07 Uiso calc R 1
C C12 0.5869(3) -0.2171(8) 0.15973(11) 0.0569(8) Uani d . 1
H H12 0.5955 -0.3131 0.1879 0.068 Uiso calc R 1
C C13 0.6808(3) -0.2087(8) 0.14557(10) 0.0476(7) Uani d . 1
H H13 0.7528 -0.2985 0.1647 0.057 Uiso calc R 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'
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 0.006 '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
N1 Ni1 O1 95.87(9)
N1 Ni1 N4 177.00(10)
O1 Ni1 N4 86.32(9)
N1 Ni1 S1 87.15(7)
O1 Ni1 S1 176.46(6)
N4 Ni1 S1 90.60(7)
C8 S1 Ni1 95.77(10)
C2 O1 Ni1 127.26(17)
C7 N1 N2 113.1(2)
C7 N1 Ni1 125.23(18)
N2 N1 Ni1 121.70(16)
C8 N2 N1 112.4(2)
C8 N3 H1 115.1
C8 N3 H2 114.2
H1 N3 H2 112.6
C9 N4 C13 118.4(2)
C9 N4 Ni1 123.42(18)
C13 N4 Ni1 118.17(19)
C6 C1 C2 119.3(2)
C6 C1 C7 118.2(2)
C2 C1 C7 122.5(2)
O1 C2 C3 119.0(2)
O1 C2 C1 123.2(2)
C3 C2 C1 117.8(2)
C4 C3 C2 122.0(2)
C4 C3 H3 119
C2 C3 H3 119
C3 C4 C5 118.9(3)
C3 C4 H4 120.5
C5 C4 H4 120.5
C6 C5 C4 121.4(2)
C6 C5 Br1 119.63(19)
C4 C5 Br1 118.9(2)
C5 C6 C1 120.5(2)
C5 C6 H6 119.8
C1 C6 H6 119.8
N1 C7 C1 125.8(2)
N1 C7 H7 117.1
C1 C7 H7 117.1
N2 C8 N3 118.8(2)
N2 C8 S1 122.9(2)
N3 C8 S1 118.2(2)
N4 C9 C10 122.3(3)
N4 C9 H9 118.8
C10 C9 H9 118.8
C11 C10 C9 118.9(3)
C11 C10 H10 120.5
C9 C10 H10 120.5
C10 C11 C12 119.4(3)
C10 C11 H11 120.3
C12 C11 H11 120.3
C11 C12 C13 119.3(3)
C11 C12 H12 120.4
C13 C12 H12 120.4
N4 C13 C12 121.7(3)
N4 C13 H13 119.2
C12 C13 H13 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.909(3)
Ni1 N1 1.858(2)
Ni1 O1 1.8576(19)
Ni1 N4 1.917(2)
Ni1 S1 2.1516(8)
S1 C8 1.735(3)
O1 C2 1.311(3)
N1 C7 1.295(3)
N1 N2 1.403(3)
N2 C8 1.289(4)
N3 C8 1.373(4)
N3 H1 0.7822
N3 H2 0.8025
N4 C9 1.341(4)
N4 C13 1.342(4)
C1 C6 1.411(4)
C1 C2 1.419(3)
C1 C7 1.429(4)
C2 C3 1.403(4)
C3 C4 1.380(4)
C3 H3 0.93
C4 C5 1.390(4)
C4 H4 0.93
C5 C6 1.358(4)
C6 H6 0.93
C7 H7 0.93
C9 C10 1.378(4)
C9 H9 0.93
C10 C11 1.367(5)
C10 H10 0.93
C11 C12 1.369(5)
C11 H11 0.93
C12 C13 1.381(4)
C12 H12 0.93
C13 H13 0.93
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
N3 H1 N2 3_745 0.78 2.31 3.095(3) 178
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
N1 Ni1 S1 C8 1.82(11)
N4 Ni1 S1 C8 -176.20(12)
N1 Ni1 O1 C2 1.9(2)
N4 Ni1 O1 C2 179.8(2)
O1 Ni1 N1 C7 -4.3(2)
S1 Ni1 N1 C7 177.6(2)
O1 Ni1 N1 N2 175.74(19)
S1 Ni1 N1 N2 -2.40(18)
C7 N1 N2 C8 -178.1(2)
Ni1 N1 N2 C8 1.9(3)
O1 Ni1 N4 C9 119.2(2)
S1 Ni1 N4 C9 -62.5(2)
O1 Ni1 N4 C13 -58.9(2)
S1 Ni1 N4 C13 119.3(2)
Ni1 O1 C2 C3 -178.72(19)
Ni1 O1 C2 C1 0.8(4)
C6 C1 C2 O1 179.6(2)
C7 C1 C2 O1 -2.0(4)
C6 C1 C2 C3 -0.9(4)
C7 C1 C2 C3 177.5(2)
O1 C2 C3 C4 179.5(3)
C1 C2 C3 C4 0.0(4)
C2 C3 C4 C5 0.6(4)
C3 C4 C5 C6 -0.3(4)
C3 C4 C5 Br1 179.4(2)
C4 C5 C6 C1 -0.7(4)
Br1 C5 C6 C1 179.7(2)
C2 C1 C6 C5 1.3(4)
C7 C1 C6 C5 -177.2(2)
N2 N1 C7 C1 -175.7(2)
Ni1 N1 C7 C1 4.3(4)
C6 C1 C7 N1 177.7(3)
C2 C1 C7 N1 -0.7(4)
N1 N2 C8 N3 177.0(2)
N1 N2 C8 S1 0.2(3)
Ni1 S1 C8 N2 -1.6(3)
Ni1 S1 C8 N3 -178.4(2)
C13 N4 C9 C10 1.0(4)
Ni1 N4 C9 C10 -177.1(2)
N4 C9 C10 C11 -0.9(5)
C9 C10 C11 C12 0.1(5)
C10 C11 C12 C13 0.6(5)
C9 N4 C13 C12 -0.2(4)
Ni1 N4 C13 C12 178.0(2)
C11 C12 C13 N4 -0.6(5)
