#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/02/2210270.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_2210270
loop_
_publ_author_name
'Yu-Liang Zhang'
_publ_section_title
{2,4-Dichloro-6-[2-(dimethylamino)ethyliminomethyl]phenolato}thiocyanatonickel(II)
_journal_coeditor_code           HG2089
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2111
_journal_page_last               m2112
_journal_paper_doi               10.1107/S1600536806030789
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Ni (C11 H12 Cl2 N2 O) (N C S)]'
_chemical_formula_moiety         'C12 H13 Cl2 N3 Ni O S'
_chemical_formula_sum            'C12 H13 Cl2 N3 Ni O S'
_chemical_formula_weight         376.92
_chemical_name_systematic
;
{2,4-Dichloro-6-[2-
(dimethylamino)ethyliminomethyl]phenolato}thiocyanatonickel(II)
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.3080(10)
_cell_length_b                   6.949(2)
_cell_length_c                   11.169(2)
_cell_measurement_reflns_used    2170
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      24.3
_cell_measurement_theta_min      2.7
_cell_volume                     1498.6(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12576
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.787
_exptl_absorpt_correction_T_max  0.6440
_exptl_absorpt_correction_T_min  0.5278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.461
_refine_ls_extinction_coef       0.0043(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0401P)²+0.7298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0989
_reflns_number_gt                1505
_reflns_number_total             1978
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2089.cif
_cod_data_source_block           I
_cod_database_code               2210270
_cod_database_fobs_code          2210270
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'
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
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_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'
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) ?
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 ?
