#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/01/2220197.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_2220197
loop_
_publ_author_name
'Khaledi, Hamid'
'Mohd Ali, Hapipah'
'Ng, Seik Weng'
_publ_section_title
;Bis[benzyl
 N'-(1H-indol-3-ylmethylene)hydrazinecarbodithioato-κ²N',S]nickel(II)
 N,N-dimethylformamide disolvate
;
_journal_coeditor_code           HB2849
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1615
_journal_paper_doi               10.1107/S1600536808038580
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Ni (C17 H14 N3 S2)2], 2C3 H7 N O'
_chemical_formula_moiety         'C34 H28 N6 Ni S4, 2(C3 H7 N O)'
_chemical_formula_sum            'C40 H42 N8 Ni O2 S4'
_chemical_formula_weight         853.77
_chemical_name_systematic
;
Bis[benzyl N'-(1H-indol-3-ylmethylene)hydrazinecarbodithioato-
κ²N',S]nickel(II) N,N-dimethylformamide
disolvate
;
_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                90.00
_cell_angle_beta                 117.921(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.3808(3)
_cell_length_b                   20.0219(7)
_cell_length_c                   10.7831(3)
_cell_measurement_reflns_used    1450
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.7
_cell_measurement_theta_min      2.2
_cell_volume                     1980.31(11)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'pubCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       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  0.0619
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13342
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.293
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0396P)²+0.2888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0942
_reflns_number_gt                2615
_reflns_number_total             3481
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2849.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1980.30(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220197
_cod_database_fobs_code          2220197
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
Ni Ni1 0.5000 0.5000 0.5000 0.01710(15) Uani d S 1
S S1 0.48640(8) 0.60841(4) 0.48343(8) 0.0236(2) Uani d . 1
S S2 0.38426(8) 0.70431(4) 0.62163(8) 0.0234(2) Uani d . 1
O O1 0.1755(3) 0.56685(12) 1.1091(2) 0.0472(7) Uani d . 1
N N1 0.2818(3) 0.49406(11) 0.9618(2) 0.0220(6) Uani d . 1
H H1 0.2520 0.5191 1.0105 0.026 Uiso calc R 1
N N2 0.4331(2) 0.51020(11) 0.6371(2) 0.0182(5) Uani d . 1
N N3 0.3953(2) 0.57357(11) 0.6685(2) 0.0192(5) Uani d . 1
N N4 0.0849(3) 0.57529(12) 1.2634(2) 0.0252(6) Uani d . 1
C C1 0.2942(3) 0.42563(14) 0.9707(3) 0.0192(6) Uani d . 1
C C2 0.2658(3) 0.38131(15) 1.0548(3) 0.0232(7) Uani d . 1
H H2 0.2351 0.3967 1.1200 0.028 Uiso calc R 1
C C3 0.2842(3) 0.31463(15) 1.0393(3) 0.0260(7) Uani d . 1
H H3 0.2647 0.2832 1.0945 0.031 Uiso calc R 1
C C4 0.3308(3) 0.29162(15) 0.9445(3) 0.0250(7) Uani d . 1
H H4 0.3412 0.2450 0.9354 0.030 Uiso calc R 1
C C5 0.3621(3) 0.33626(15) 0.8636(3) 0.0219(7) Uani d . 1
H H5 0.3955 0.3205 0.8005 0.026 Uiso calc R 1
C C6 0.3437(3) 0.40438(14) 0.8763(3) 0.0187(6) Uani d . 1
C C7 0.3625(3) 0.46401(14) 0.8099(3) 0.0188(6) Uani d . 1
C C8 0.3220(3) 0.51697(15) 0.8678(3) 0.0223(7) Uani d . 1
H H8 0.3227 0.5627 0.8443 0.027 Uiso calc R 1
C C9 0.4138(3) 0.46239(15) 0.7091(3) 0.0198(7) Uani d . 1
H H9 0.4382 0.4191 0.6907 0.024 Uiso calc R 1
C C10 0.4193(3) 0.62076(14) 0.6009(3) 0.0191(6) Uani d . 1
C C11 0.3353(3) 0.70343(15) 0.7620(3) 0.0245(7) Uani d . 1
H H11A 0.4028 0.6726 0.8354 0.029 Uiso calc R 1
H H11B 0.3535 0.7487 0.8039 0.029 Uiso calc R 1
C C12 0.1817(3) 0.68378(14) 0.7277(3) 0.0206(7) Uani d . 1
C C13 0.0673(3) 0.68232(15) 0.5927(3) 0.0259(7) Uani d . 1
H H13 0.0838 0.6939 0.5159 0.031 Uiso calc R 1
C C14 -0.0716(3) 0.66398(16) 0.5687(3) 0.0309(8) Uani d . 1
H H14 -0.1490 0.6622 0.4754 0.037 Uiso calc R 1
C C15 -0.0977(3) 0.64846(16) 0.6793(3) 0.0320(8) Uani d . 1
H H15 -0.1930 0.6364 0.6627 0.038 Uiso calc R 1
C C16 0.0152(3) 0.65049(15) 0.8139(3) 0.0291(8) Uani d . 1
H H16 -0.0020 0.6398 0.8908 0.035 Uiso calc R 1
C C17 0.1540(3) 0.66816(15) 0.8379(3) 0.0243(7) Uani d . 1
H H17 0.2312 0.6696 0.9313 0.029 Uiso calc R 1
C C18 0.1381(4) 0.54196(18) 1.1919(3) 0.0376(9) Uani d . 1
H H18 0.1485 0.4950 1.2054 0.045 Uiso calc R 1
C C19 0.0701(3) 0.64730(15) 1.2501(3) 0.0289(8) Uani d . 1
H H19A 0.0755 0.6616 1.1658 0.043 Uiso calc R 1
H H19B 0.1489 0.6684 1.3329 0.043 Uiso calc R 1
H H19C -0.0241 0.6606 1.2427 0.043 Uiso calc R 1
C C20 0.0490(3) 0.54232(15) 1.3634(3) 0.0293(7) Uani d . 1
H H20A 0.0590 0.4939 1.3579 0.044 Uiso calc R 1
H H20B -0.0516 0.5531 1.3412 0.044 Uiso calc R 1
H H20C 0.1154 0.5578 1.4584 0.044 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 0.0000 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'
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
N2 Ni1 N2 3_666 . 180.0
N2 Ni1 S1 3_666 . 94.36(7)
N2 Ni1 S1 . . 85.64(7)
N2 Ni1 S1 3_666 3_666 85.64(7)
N2 Ni1 S1 . 3_666 94.36(7)
S1 Ni1 S1 . 3_666 180.0
C10 S1 Ni1 . . 96.64(10)
C10 S2 C11 . . 104.76(13)
C8 N1 C1 . . 109.9(2)
C8 N1 H1 . . 125.1
C1 N1 H1 . . 125.1
C9 N2 N3 . . 112.2(2)
C9 N2 Ni1 . . 126.4(2)
N3 N2 Ni1 . . 121.46(17)
C10 N3 N2 . . 111.9(2)
C18 N4 C20 . . 121.8(3)
C18 N4 C19 . . 119.9(3)
C20 N4 C19 . . 118.2(2)
N1 C1 C2 . . 129.6(3)
N1 C1 C6 . . 107.8(2)
C2 C1 C6 . . 122.6(3)
C3 C2 C1 . . 117.2(3)
C3 C2 H2 . . 121.4
C1 C2 H2 . . 121.4
C2 C3 C4 . . 121.7(3)
C2 C3 H3 . . 119.2
C4 C3 H3 . . 119.2
C5 C4 C3 . . 120.7(3)
C5 C4 H4 . . 119.7
C3 C4 H4 . . 119.7
C4 C5 C6 . . 119.0(3)
C4 C5 H5 . . 120.5
C6 C5 H5 . . 120.5
C5 C6 C1 . . 118.8(3)
C5 C6 C7 . . 134.5(3)
C1 C6 C7 . . 106.7(2)
C8 C7 C9 . . 131.5(3)
C8 C7 C6 . . 105.5(2)
C9 C7 C6 . . 123.0(3)
N1 C8 C7 . . 110.1(3)
N1 C8 H8 . . 125.0
C7 C8 H8 . . 125.0
N2 C9 C7 . . 131.1(3)
N2 C9 H9 . . 114.5
C7 C9 H9 . . 114.5
N3 C10 S1 . . 124.2(2)
N3 C10 S2 . . 121.5(2)
S1 C10 S2 . . 114.26(16)
C12 C11 S2 . . 118.4(2)
C12 C11 H11A . . 107.7
S2 C11 H11A . . 107.7
C12 C11 H11B . . 107.7
S2 C11 H11B . . 107.7
H11A C11 H11B . . 107.1
C17 C12 C13 . . 118.5(3)
C17 C12 C11 . . 118.0(2)
C13 C12 C11 . . 123.5(3)
C12 C13 C14 . . 120.4(3)
C12 C13 H13 . . 119.8
C14 C13 H13 . . 119.8
C15 C14 C13 . . 120.4(3)
C15 C14 H14 . . 119.8
C13 C14 H14 . . 119.8
C14 C15 C16 . . 119.4(3)
C14 C15 H15 . . 120.3
C16 C15 H15 . . 120.3
C15 C16 C17 . . 120.2(3)
C15 C16 H16 . . 119.9
C17 C16 H16 . . 119.9
C12 C17 C16 . . 121.0(3)
C12 C17 H17 . . 119.5
C16 C17 H17 . . 119.5
O1 C18 N4 . . 125.3(3)
O1 C18 H18 . . 117.3
N4 C18 H18 . . 117.3
N4 C19 H19A . . 109.5
N4 C19 H19B . . 109.5
H19A C19 H19B . . 109.5
N4 C19 H19C . . 109.5
H19A C19 H19C . . 109.5
H19B C19 H19C . . 109.5
N4 C20 H20A . . 109.5
N4 C20 H20B . . 109.5
H20A C20 H20B . . 109.5
N4 C20 H20C . . 109.5
H20A C20 H20C . . 109.5
H20B C20 H20C . . 109.5
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 N2 3_666 1.916(2) ?
Ni1 N2 . 1.916(2) yes
Ni1 S1 . 2.1770(7) yes
Ni1 S1 3_666 2.1770(7) ?
S1 C10 . 1.725(3) ?
S2 C10 . 1.748(3) ?
S2 C11 . 1.808(3) ?
O1 C18 . 1.233(4) ?
N1 C8 . 1.346(3) ?
N1 C1 . 1.375(3) ?
N1 H1 . 0.8800 ?
N2 C9 . 1.306(3) ?
N2 N3 . 1.416(3) ?
N3 C10 . 1.287(3) ?
N4 C18 . 1.321(4) ?
N4 C20 . 1.454(4) ?
N4 C19 . 1.450(4) ?
C1 C2 . 1.395(4) ?
C1 C6 . 1.404(4) ?
C2 C3 . 1.370(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.398(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.390(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.393(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.451(4) ?
C7 C8 . 1.391(4) ?
C7 C9 . 1.418(4) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C11 C12 . 1.511(4) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C17 . 1.383(4) ?
C12 C13 . 1.382(4) ?
C13 C14 . 1.390(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.377(4) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.375(4) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.385(4) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 0.88 1.86 2.739(3) 175 no
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
N2 Ni1 S1 C10 3_666 177.84(11)
N2 Ni1 S1 C10 . -2.16(11)
S1 Ni1 N2 C9 . -177.9(2)
S1 Ni1 N2 C9 3_666 2.1(2)
S1 Ni1 N2 N3 . 3.52(18)
S1 Ni1 N2 N3 3_666 -176.48(18)
C9 N2 N3 C10 . 177.8(2)
Ni1 N2 N3 C10 . -3.5(3)
C8 N1 C1 C2 . 179.3(3)
C8 N1 C1 C6 . -0.5(3)
N1 C1 C2 C3 . 178.4(3)
C6 C1 C2 C3 . -1.9(4)
C1 C2 C3 C4 . 0.7(4)
C2 C3 C4 C5 . 0.8(4)
C3 C4 C5 C6 . -1.2(4)
C4 C5 C6 C1 . 0.0(4)
C4 C5 C6 C7 . -178.9(3)
N1 C1 C6 C5 . -178.6(2)
C2 C1 C6 C5 . 1.5(4)
N1 C1 C6 C7 . 0.6(3)
C2 C1 C6 C7 . -179.3(3)
C5 C6 C7 C8 . 178.6(3)
C1 C6 C7 C8 . -0.5(3)
C5 C6 C7 C9 . -2.0(5)
C1 C6 C7 C9 . 179.0(2)
C1 N1 C8 C7 . 0.2(3)
C9 C7 C8 N1 . -179.2(3)
C6 C7 C8 N1 . 0.2(3)
N3 N2 C9 C7 . 0.1(4)
Ni1 N2 C9 C7 . -178.5(2)
C8 C7 C9 N2 . -2.8(5)
C6 C7 C9 N2 . 177.9(3)
N2 N3 C10 S1 . 1.1(3)
N2 N3 C10 S2 . -179.25(17)
Ni1 S1 C10 N3 . 1.2(2)
Ni1 S1 C10 S2 . -178.47(13)
C11 S2 C10 N3 . 6.4(3)
C11 S2 C10 S1 . -173.95(15)
C10 S2 C11 C12 . -80.3(2)
S2 C11 C12 C17 . 165.3(2)
S2 C11 C12 C13 . -16.5(4)
C17 C12 C13 C14 . -1.5(4)
C11 C12 C13 C14 . -179.7(3)
C12 C13 C14 C15 . 1.4(5)
C13 C14 C15 C16 . -0.7(5)
C14 C15 C16 C17 . 0.1(5)
C13 C12 C17 C16 . 0.9(4)
C11 C12 C17 C16 . 179.2(3)
C15 C16 C17 C12 . -0.2(5)
C20 N4 C18 O1 . -177.4(3)
C19 N4 C18 O1 . -1.6(5)
