##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
Chlorido[1-(4,5-dihydro-1,3-thiazol-2-yl-κN)ethanone
thiosemicarbazonato-κ²N¹,S]nickel(II)
;
_chemical_formula_moiety     'C6 H9 Cl N4 Ni S2'
_chemical_formula_sum     'C6 H9 Cl N4 Ni S2'
_chemical_formula_iupac     '[Ni (C6 H9 N4 S2) Cl]'
_chemical_formula_weight     295.45
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     9.656(2)
_cell_length_b     10.617(2)
_cell_length_c     11.187(3)
_cell_angle_alpha     90
_cell_angle_beta     112.874(4)
_cell_angle_gamma     90
_cell_volume     1056.7(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     912
_cell_measurement_theta_min     2.29
_cell_measurement_theta_max     26.265
_cell_measurement_temperature     298(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'brown'
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.857
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     600
_exptl_absorpt_coefficient_mu     2.447
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min     0.615
_exptl_absorpt_correction_T_max     0.828
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine--focus sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker SMART 1000 CCD'
_diffrn_measurement_method     ω
_diffrn_reflns_number     2554
_diffrn_reflns_av_R_equivalents     0.0303
_diffrn_reflns_theta_min     2.29
_diffrn_reflns_theta_max     28.32
_diffrn_reflns_theta_full     27.5
_diffrn_measured_fraction_theta_max     0.971
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     14
_refine_special_details
;
 Refinement of F² against ALL reflections. The weighted
 R--factor wR and goodness of fit S are based on
 F², conventional R--factors R are based on F,
 with F set to zero for negative F². The threshold expression
 of F² > σ(F²) is used only for calculating
 R--factors(gt) etc. and is not relevant to the choice of
 reflections for refinement. R--factors based on F² are
 statistically about twice as large as those based on F, and
 R--factors based on ALL data will be even larger.
;
_reflns_number_total     2554
_reflns_number_gt     1758
_reflns_threshold_expression     2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0604
_refine_ls_R_factor_gt     0.0341
_refine_ls_wR_factor_ref     0.0755
_refine_ls_goodness_of_fit_ref     1.053
_refine_ls_restrained_S_all     1.053
_refine_ls_number_reflns     2554
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0327P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.331
_refine_diff_density_min     -0.341
_refine_ls_extinction_method     none
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'
    Cl Cl 0.1484 0.1585 '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'
    S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'publCIF  (Westrip, 2010)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.3581(3) 0.6235(2) 0.0701(2) 0.0334(6) Uani d . 1 . .
    C C2 0.3833(3) 0.4480(2) 0.1999(3) 0.0426(7) Uani d . 1 . .
    H H2A 0.4210 0.4551 0.2936 0.051 Uiso calc R 1 . .
    H H2B 0.4086 0.3650 0.1783 0.051 Uiso calc R 1 . .
    C C3 0.2123(3) 0.4657(3) 0.1417(3) 0.0504(8) Uani d . 1 . .
    H H3A 0.1753 0.4759 0.2103 0.06 Uiso calc R 1 . .
    H H3B 0.1639 0.3926 0.0905 0.06 Uiso calc R 1 . .
    C C4 0.4210(3) 0.7245(2) 0.0176(2) 0.0340(6) Uani d . 1 . .
    C C5 0.3317(3) 0.8206(3) -0.0777(3) 0.0460(7) Uani d . 1 . .
    H H5A 0.3662 0.9032 -0.0445 0.069 Uiso calc R 1 . .
    H H5B 0.2275 0.8121 -0.0919 0.069 Uiso calc R 1 . .
    H H5C 0.3438 0.8085 -0.1581 0.069 Uiso calc R 1 . .
    C C6 0.7922(3) 0.7897(2) 0.0918(3) 0.0385(6) Uani d . 1 . .
    Cl Cl 0.75176(8) 0.43164(6) 0.31254(7) 0.0474(2) Uani d . 1 . .
    N N1 0.4522(2) 0.5445(2) 0.1476(2) 0.0361(5) Uani d . 1 . .
    N N2 0.5671(2) 0.71858(19) 0.0663(2) 0.0333(5) Uani d . 1 . .
    N N3 0.6450(2) 0.8074(2) 0.0291(2) 0.0399(6) Uani d . 1 . .
    N N4 0.8837(3) 0.8692(2) 0.0669(2) 0.0552(7) Uani d . 1 . .
    H H4A 0.8472 0.9292 0.0121 0.066 Uiso calc R 1 . .
    H H4B 0.9795 0.8606 0.1057 0.066 Uiso calc R 1 . .
    Ni Ni 0.65556(4) 0.58829(3) 0.18229(3) 0.03380(12) Uani d . 1 . .
    S S1 0.17043(8) 0.60537(7) 0.03983(8) 0.0493(2) Uani d . 1 . .
    S S2 0.86881(8) 0.66908(7) 0.20402(7) 0.0465(2) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0295(14) 0.0359(14) 0.0342(15) -0.0026(11) 0.0119(12) -0.0042(12)
    C2 0.0445(17) 0.0365(15) 0.0506(19) -0.0033(13) 0.0225(15) 0.0017(13)
    C3 0.0422(17) 0.0473(17) 0.061(2) -0.0105(14) 0.0187(16) 0.0021(15)
    C4 0.0331(15) 0.0317(14) 0.0340(15) 0.0010(11) 0.0094(12) -0.0004(11)
    C5 0.0394(16) 0.0458(17) 0.0475(18) 0.0044(13) 0.0112(14) 0.0105(14)
    C6 0.0358(15) 0.0396(15) 0.0441(17) -0.0061(12) 0.0199(13) -0.0028(13)
    Cl 0.0398(4) 0.0440(4) 0.0541(5) 0.0087(3) 0.0137(3) 0.0101(3)
    N1 0.0314(12) 0.0359(12) 0.0403(13) -0.0027(10) 0.0131(10) 0.0025(10)
    N2 0.0303(12) 0.0333(12) 0.0369(13) -0.0006(9) 0.0137(10) 0.0004(10)
    N3 0.0393(13) 0.0383(13) 0.0458(14) -0.0047(10) 0.0206(12) 0.0030(11)
    N4 0.0351(14) 0.0576(16) 0.0727(19) -0.0084(12) 0.0207(13) 0.0112(14)
    Ni 0.02818(19) 0.03349(19) 0.0382(2) 0.00139(15) 0.01121(15) 0.00176(15)
    S1 0.0281(4) 0.0485(5) 0.0661(5) -0.0031(3) 0.0126(4) 0.0033(4)
    S2 0.0293(4) 0.0486(4) 0.0578(5) -0.0008(3) 0.0128(3) 0.0060(4)
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix. The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry. An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
    C1 N1 . 1.292(3) ?
    C1 C4 . 1.463(3) ?
    C1 S1 . 1.720(3) ?
    C2 N1 . 1.462(3) ?
    C2 C3 . 1.533(4) ?
    C2 H2A . 0.97 ?
    C2 H2B . 0.97 ?
    C3 S1 . 1.817(3) ?
    C3 H3A . 0.97 ?
    C3 H3B . 0.97 ?
    C4 N2 . 1.302(3) ?
    C4 C5 . 1.485(3) ?
    C5 H5A . 0.96 ?
    C5 H5B . 0.96 ?
    C5 H5C . 0.96 ?
    C6 N4 . 1.327(3) ?
    C6 N3 . 1.332(3) ?
    C6 S2 . 1.743(3) ?
    Cl Ni . 2.1679(8) ?
    N1 Ni . 1.905(2) ?
    N2 N3 . 1.367(3) ?
    N2 Ni . 1.861(2) ?
    N4 H4A . 0.86 ?
    N4 H4B . 0.86 ?
    Ni S2 . 2.1554(9) ?
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
    N1 C1 C4 . . 116.9(2) ?
    N1 C1 S1 . . 118.2(2) ?
    C4 C1 S1 . . 124.9(2) ?
    N1 C2 C3 . . 109.1(2) ?
    N1 C2 H2A . . 109.9 ?
    C3 C2 H2A . . 109.9 ?
    N1 C2 H2B . . 109.9 ?
    C3 C2 H2B . . 109.9 ?
    H2A C2 H2B . . 108.3 ?
    C2 C3 S1 . . 107.85(19) ?
    C2 C3 H3A . . 110.1 ?
    S1 C3 H3A . . 110.1 ?
    C2 C3 H3B . . 110.1 ?
    S1 C3 H3B . . 110.1 ?
    H3A C3 H3B . . 108.4 ?
    N2 C4 C1 . . 110.4(2) ?
    N2 C4 C5 . . 124.5(2) ?
    C1 C4 C5 . . 125.2(2) ?
    C4 C5 H5A . . 109.5 ?
    C4 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C4 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    N4 C6 N3 . . 117.4(3) ?
    N4 C6 S2 . . 119.2(2) ?
    N3 C6 S2 . . 123.4(2) ?
    C1 N1 C2 . . 114.4(2) ?
    C1 N1 Ni . . 112.27(18) ?
    C2 N1 Ni . . 133.07(18) ?
    C4 N2 N3 . . 118.3(2) ?
    C4 N2 Ni . . 117.17(18) ?
    N3 N2 Ni . . 124.56(16) ?
    C6 N3 N2 . . 110.0(2) ?
    C6 N4 H4A . . 120 ?
    C6 N4 H4B . . 120 ?
    H4A N4 H4B . . 120 ?
    N2 Ni N1 . . 83.24(9) ?
    N2 Ni S2 . . 86.68(7) ?
    N1 Ni S2 . . 169.68(7) ?
    N2 Ni Cl . . 177.76(7) ?
    N1 Ni Cl . . 95.06(7) ?
    S2 Ni Cl . . 95.08(3) ?
    C1 S1 C3 . . 90.43(13) ?
    C6 S2 Ni . . 95.27(9) ?
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
    N1 C2 C3 S1 . . . . -3.3(3) ?
    N1 C1 C4 N2 . . . . -3.2(3) ?
    S1 C1 C4 N2 . . . . 174.88(19) ?
    N1 C1 C4 C5 . . . . 176.9(2) ?
    S1 C1 C4 C5 . . . . -5.1(4) ?
    C4 C1 N1 C2 . . . . 178.3(2) ?
    S1 C1 N1 C2 . . . . 0.1(3) ?
    C4 C1 N1 Ni . . . . 3.7(3) ?
    S1 C1 N1 Ni . . . . -174.50(12) ?
    C3 C2 N1 C1 . . . . 2.2(3) ?
    C3 C2 N1 Ni . . . . 175.34(19) ?
    C1 C4 N2 N3 . . . . -179.1(2) ?
    C5 C4 N2 N3 . . . . 0.8(4) ?
    C1 C4 N2 Ni . . . . 1.1(3) ?
    C5 C4 N2 Ni . . . . -179.0(2) ?
    N4 C6 N3 N2 . . . . -179.5(2) ?
    S2 C6 N3 N2 . . . . 0.1(3) ?
    C4 N2 N3 C6 . . . . 177.7(2) ?
    Ni N2 N3 C6 . . . . -2.5(3) ?
    C4 N2 Ni N1 . . . . 0.65(19) ?
    N3 N2 Ni N1 . . . . -179.2(2) ?
    C4 N2 Ni S2 . . . . -177.17(19) ?
    N3 N2 Ni S2 . . . . 3.02(19) ?
    C1 N1 Ni N2 . . . . -2.43(19) ?
    C2 N1 Ni N2 . . . . -175.7(3) ?
    C1 N1 Ni S2 . . . . 9.8(5) ?
    C2 N1 Ni S2 . . . . -163.5(3) ?
    C1 N1 Ni Cl . . . . 179.02(18) ?
    C2 N1 Ni Cl . . . . 5.7(2) ?
    N1 C1 S1 C3 . . . . -1.9(2) ?
    C4 C1 S1 C3 . . . . -179.9(2) ?
    C2 C3 S1 C1 . . . . 2.9(2) ?
    N4 C6 S2 Ni . . . . -178.7(2) ?
    N3 C6 S2 Ni . . . . 1.6(2) ?
    N2 Ni S2 C6 . . . . -2.03(11) ?
    N1 Ni S2 C6 . . . . -14.2(4) ?
    Cl Ni S2 C6 . . . . 176.58(9) ?
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
    N4 H4B Cl 2_755 0.86 2.51 3.310(3) 155.4
    N4 H4A Cl 4_575 0.86 2.53 3.373(3) 165.8
    C3 H3B S1 3_565 0.97 2.98 3.537(3) 117.6
data_global
_journal_date_recd_electronic     2010-11-22
_journal_date_accepted     2010-12-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      1
_journal_page_first     m79
_journal_page_last     m79
_journal_paper_category     QM
_journal_coeditor_code     RK2251
_publ_contact_author_name     'E. Viñuelas--Zahínos'
_publ_contact_author_address
;
Departamento de Quimica Organica e Inorganica
Facultad de Ciencias
Universidad de Extremadura
Badajoz
Spain
;
_publ_contact_author_email     emilvin@unex.es
_publ_contact_author_fax     '0034 924271149'
_publ_contact_author_phone     '0034 924289395'
_publ_section_title
;
Chlorido[1-(4,5-dihydro-1,3-thiazol-2-yl-κN)ethanone
thiosemicarbazonato-κ²N¹,S]nickel(II)
;
loop_
    _publ_author_name
    _publ_author_address
    'Viñuelas-Zahínos, Emilio'
;
Departamento de Quimica Organica e Inorganica
Facultad de Ciencias
Universidad de Extremadura
Badajoz
Spain
;
    'Luna-Giles, Francisco'
;
Departamento de Quimica Organica e Inorganica
Facultad de Ciencias
Universidad de Extremadura
Badajoz
Spain
;
    'Torres-García, Pablo'
;
Departamento de Quimica Organica e Inorganica
Facultad de Ciencias
Universidad de Extremadura
Badajoz
Spain
;
    'Bernalte-García, Álvaro'
;
Departamento de Quimica Organica e Inorganica
Facultad de Ciencias
Universidad de Extremadura
Badajoz
Spain
;
