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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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.                                        #
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# 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          #
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#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2006-08-04
_journal_date_accepted     2006-08-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      9
_journal_page_first     m2111
_journal_page_last     m2112
_journal_paper_category     EM
_journal_coeditor_code     HG2089
_publ_contact_author_name     'Dr. Yu-Liang Zhang'
_publ_contact_author_address
;
Department of Chemistry
East China University of Science and Technology
Shanghai 200237
People's Republic of China
;
_publ_contact_author_email     yuliang_zhang@sohu.com
_publ_contact_author_fax     '86 21 64252214'
_publ_contact_author_phone     '86 21 64252214'
_publ_section_title
;
{2,4-Dichloro-6-[2-
(dimethylamino)ethyliminomethyl]phenolato}thiocyanatonickel(II)
;
loop_
    _publ_author_name
    _publ_author_address
    'Yu-Liang Zhang'
;
Department of Chemistry
East China University of Science and Technology
Shanghai 200237
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
{2,4-Dichloro-6-[2-
(dimethylamino)ethyliminomethyl]phenolato}thiocyanatonickel(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H13 Cl2 N3 Ni O S'
_chemical_formula_sum     'C12 H13 Cl2 N3 Ni O S'
_chemical_formula_iupac     '[Ni (C11 H12 Cl2 N2 O) (N C S)]'
_chemical_formula_weight     376.92
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n m a'
_symmetry_space_group_name_Hall     '-P 2ac 2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z'
    'x+1/2, -y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z'
    '-x-1/2, y-1/2, z-1/2'
_cell_length_a     19.3080(10)
_cell_length_b     6.949(2)
_cell_length_c     11.169(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1498.6(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2170
_cell_measurement_theta_min     2.7
_cell_measurement_theta_max     24.3
_cell_measurement_temperature     291(2)
_exptl_crystal_description     block
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.41
_exptl_crystal_size_mid     0.32
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.671
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     768
_exptl_absorpt_coefficient_mu     1.787
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.5278
_exptl_absorpt_correction_T_max     0.6440
_exptl_special_details
;
;
_diffrn_ambient_temperature     291(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 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12576
_diffrn_reflns_av_R_equivalents     0.0542
_diffrn_reflns_av_sigmaI/netI     0.0450
_diffrn_reflns_theta_min     2.11
_diffrn_reflns_theta_max     28.35
_diffrn_reflns_theta_full     28.35
_diffrn_measured_fraction_theta_max     0.976
_diffrn_measured_fraction_theta_full     0.976
_diffrn_reflns_limit_h_min     -25
_diffrn_reflns_limit_h_max     24
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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 > 2sigma(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     1978
_reflns_number_gt     1505
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0605
_refine_ls_R_factor_gt     0.0410
_refine_ls_wR_factor_gt     0.0913
_refine_ls_wR_factor_ref     0.0989
_refine_ls_goodness_of_fit_ref     1.038
_refine_ls_restrained_S_all     1.038
_refine_ls_number_reflns     1978
_refine_ls_number_parameters     123
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0401P)²+0.7298P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.386
_refine_diff_density_min     -0.461
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.0043(7)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    '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'
    'S' 'S' 0.1246 0.1234
                         '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'
    'Ni' 'Ni' 0.3393 1.1124
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 1998)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997a)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997a)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material     'SHELXTL'
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
    Ni Ni1 0.17716(2) 0.2500 0.35610(4) 0.03625(17) Uani d S 1 . .
    Cl Cl1 0.11030(6) 0.2500 0.76849(10) 0.0730(4) Uani d S 1 . .
    Cl Cl2 -0.15792(6) 0.2500 0.64823(11) 0.0670(4) Uani d S 1 . .
    S S1 0.41005(6) 0.2500 0.46446(12) 0.0705(4) Uani d S 1 . .
    O O1 0.13490(13) 0.2500 0.5109(2) 0.0473(7) Uani d S 1 . .
    N N1 0.08867(16) 0.2500 0.2760(3) 0.0422(7) Uani d S 1 . .
    N N2 0.21763(17) 0.2500 0.1859(3) 0.0539(9) Uani d S 1 . .
    N N3 0.26849(18) 0.2500 0.4247(3) 0.0622(10) Uani d S 1 . .
    C C1 0.06906(18) 0.2500 0.5370(3) 0.0359(8) Uani d S 1 . .
    C C2 0.0479(2) 0.2500 0.6584(3) 0.0430(9) Uani d S 1 . .
    C C3 -0.0200(2) 0.2500 0.6916(3) 0.0437(9) Uani d S 1 . .
    H H3 -0.0321 0.2500 0.7723 0.052 Uiso calc SR 1 . .
    C C4 -0.07144(19) 0.2500 0.6034(4) 0.0431(9) Uani d S 1 . .
    C C5 -0.05422(19) 0.2500 0.4867(4) 0.0433(9) Uani d S 1 . .
    H H5 -0.0890 0.2500 0.4292 0.052 Uiso calc SR 1 . .
    C C6 0.01512(18) 0.2500 0.4505(3) 0.0375(8) Uani d S 1 . .
    C C7 0.0289(2) 0.2500 0.3246(3) 0.0412(9) Uani d S 1 . .
    H H7 -0.0092 0.2500 0.2736 0.049 Uiso calc SR 1 . .
    C C8 0.0937(2) 0.2500 0.1441(4) 0.0669(14) Uani d S 1 . .
    H H8A 0.0910 0.3793 0.1142 0.080 Uiso d PR 0.50 . .
    H H8B 0.0561 0.1772 0.1107 0.080 Uiso d PR 0.50 . .
    C C9 0.1591(3) 0.1653(10) 0.1098(5) 0.0570(17) Uani d P 0.50 . .
    H H9A 0.1572 0.0286 0.1217 0.068 Uiso d PR 0.50 . .
    H H9B 0.1682 0.1894 0.0267 0.068 Uiso d PR 0.50 . .
    C C10 0.2601(3) 0.0825(6) 0.1624(4) 0.1046(17) Uani d . 1 . .
    H H10A 0.2749 0.0839 0.0803 0.157 Uiso calc R 1 . .
    H H10B 0.2336 -0.0320 0.1773 0.157 Uiso calc R 1 . .
    H H10C 0.2999 0.0844 0.2139 0.157 Uiso calc R 1 . .
    C C11 0.3277(2) 0.2500 0.4409(4) 0.0492(10) Uani d S 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
    Ni1 0.0265(3) 0.0520(3) 0.0302(3) 0.000 0.00247(18) 0.000
    Cl1 0.0546(7) 0.1269(11) 0.0377(6) 0.000 -0.0053(5) 0.000
    Cl2 0.0391(6) 0.1019(10) 0.0598(7) 0.000 0.0161(5) 0.000
    S1 0.0344(6) 0.1111(11) 0.0659(8) 0.000 -0.0025(5) 0.000
    O1 0.0305(13) 0.0768(19) 0.0346(14) 0.000 0.0011(11) 0.000
    N1 0.0356(17) 0.059(2) 0.0317(16) 0.000 0.0017(13) 0.000
    N2 0.0371(19) 0.088(3) 0.0364(18) 0.000 0.0081(14) 0.000
    N3 0.0355(19) 0.107(3) 0.044(2) 0.000 -0.0007(16) 0.000
    C1 0.039(2) 0.0373(19) 0.0316(19) 0.000 0.0027(15) 0.000
    C2 0.045(2) 0.048(2) 0.035(2) 0.000 -0.0004(16) 0.000
    C3 0.048(2) 0.048(2) 0.035(2) 0.000 0.0120(17) 0.000
    C4 0.0307(19) 0.051(2) 0.047(2) 0.000 0.0091(16) 0.000
    C5 0.0340(19) 0.052(2) 0.044(2) 0.000 0.0017(16) 0.000
    C6 0.0347(19) 0.042(2) 0.036(2) 0.000 0.0044(15) 0.000
    C7 0.0334(19) 0.053(2) 0.037(2) 0.000 -0.0033(15) 0.000
    C8 0.049(3) 0.118(4) 0.034(2) 0.000 0.0057(19) 0.000
    C9 0.045(3) 0.092(5) 0.034(3) -0.002(3) -0.002(2) -0.005(3)
    C10 0.161(5) 0.067(2) 0.086(3) -0.003(3) 0.070(3) -0.013(2)
    C11 0.039(2) 0.073(3) 0.035(2) 0.000 0.0053(17) 0.000
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    Ni1 O1 . 1.912(3) yes
    Ni1 N3 . 1.923(4) yes
    Ni1 N1 . 1.929(3) yes
    Ni1 N2 . 2.056(3) yes
    Cl1 C2 . 1.722(4) ?
    Cl2 C4 . 1.743(4) ?
    S1 C11 . 1.611(4) ?
    O1 C1 . 1.304(4) ?
    N1 C7 . 1.276(5) ?
    N1 C8 . 1.476(5) ?
    N2 C10 . 1.447(5) ?
    N2 C10 7_565 1.447(5) ?
    N2 C9 . 1.531(6) ?
    N2 C9 7_565 1.531(6) ?
    N3 C11 . 1.158(5) ?
    C1 C2 . 1.416(5) ?
    C1 C6 . 1.421(5) ?
    C2 C3 . 1.363(5) ?
    C3 C4 . 1.399(6) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.344(6) ?
    C5 C6 . 1.399(5) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.431(5) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.444(7) ?
    C8 C9 7_565 1.444(7) ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C9 C9 7_565 1.177(14) ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
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
    O1 Ni1 N3 . . 91.78(13) yes
    O1 Ni1 N1 . . 92.39(11) yes
    N3 Ni1 N1 . . 175.83(14) yes
    O1 Ni1 N2 . . 177.08(12) yes
    N3 Ni1 N2 . . 91.14(14) yes
    N1 Ni1 N2 . . 84.69(13) yes
    C1 O1 Ni1 . . 128.2(2) ?
    C7 N1 C8 . . 119.0(3) ?
    C7 N1 Ni1 . . 127.2(3) ?
    C8 N1 Ni1 . . 113.9(3) ?
    C10 N2 C10 . 7_565 107.1(4) ?
    C10 N2 C9 . . 90.5(3) ?
    C10 N2 C9 7_565 . 128.8(4) ?
    C10 N2 C9 . 7_565 128.8(4) ?
    C10 N2 C9 7_565 7_565 90.5(3) ?
    C9 N2 C9 . 7_565 45.2(5) ?
    C10 N2 Ni1 . . 112.5(2) ?
    C10 N2 Ni1 7_565 . 112.5(2) ?
    C9 N2 Ni1 . . 103.4(3) ?
    C9 N2 Ni1 7_565 . 103.4(3) ?
    C11 N3 Ni1 . . 165.5(3) ?
    O1 C1 C2 . . 119.7(3) ?
    O1 C1 C6 . . 124.2(3) ?
    C2 C1 C6 . . 116.1(3) ?
    C3 C2 C1 . . 122.6(4) ?
    C3 C2 Cl1 . . 118.6(3) ?
    C1 C2 Cl1 . . 118.8(3) ?
    C2 C3 C4 . . 119.4(4) ?
    C2 C3 H3 . . 120.3 ?
    C4 C3 H3 . . 120.3 ?
    C5 C4 C3 . . 120.5(4) ?
    C5 C4 Cl2 . . 121.0(3) ?
    C3 C4 Cl2 . . 118.5(3) ?
    C4 C5 C6 . . 121.1(4) ?
    C4 C5 H5 . . 119.4 ?
    C6 C5 H5 . . 119.4 ?
    C5 C6 C1 . . 120.3(3) ?
    C5 C6 C7 . . 117.5(3) ?
    C1 C6 C7 . . 122.2(3) ?
    N1 C7 C6 . . 125.9(3) ?
    N1 C7 H7 . . 117.1 ?
    C6 C7 H7 . . 117.1 ?
    C9 C8 C9 . 7_565 48.1(6) ?
    C9 C8 N1 . . 108.8(4) ?
    C9 C8 N1 7_565 . 108.8(4) ?
    C9 C8 H8A . . 109.7 ?
    C9 C8 H8A 7_565 . 64.8 ?
    N1 C8 H8A . . 110.1 ?
    C9 C8 H8B . . 110.1 ?
    C9 C8 H8B 7_565 . 140.6 ?
    N1 C8 H8B . . 109.7 ?
    H8A C8 H8B . . 108.4 ?
    C9 C9 C8 7_565 . 66.0(3) ?
    C9 C9 N2 7_565 . 67.4(3) ?
    C8 C9 N2 . . 110.0(4) ?
    C9 C9 H9A 7_565 . 171.8 ?
    C8 C9 H9A . . 109.5 ?
    N2 C9 H9A . . 109.4 ?
    C9 C9 H9B 7_565 . 79.9 ?
    C8 C9 H9B . . 110.2 ?
    N2 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 108.2 ?
    N2 C10 H10A . . 109.5 ?
    N2 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    N2 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    N3 C11 S1 . . 179.6(4) ?
