#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/06/2210633.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_2210633
loop_
_publ_author_name
'Ali, Hapipah M.'
'Najwa, Mohd Idris'
'Xie, Ming-Jin'
'Ng, Seik Weng'
_publ_section_title
;
 Bis(2-methyl-1H-indole-3-carbaldehyde
 4-hydroxybenzoylhydrazonato-κ²N,O)nickel(II)
 N,N-dimethylformamide disolvate dihydrate
;
_journal_coeditor_code           HB2145
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2625
_journal_page_last               m2626
_journal_paper_doi               10.1107/S1600536806037172
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Ni (C17 H14 N3 O2)2], 2C3 H7 N O, 2H2 O'
_chemical_formula_moiety         'C34 H28 N6 Ni O4, 2C3 H7 N O, 2H2 O'
_chemical_formula_sum            'C40 H46 N8 Ni O8'
_chemical_formula_weight         825.56
_chemical_name_systematic
;
Bis(2-methyl-1H-indole-3-carbaldehyde
4-hydroxybenzoylhydrazonato-κ²N,O)nickel(II)
N,N-dimethylformamide disolvate dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.3360(10)
_cell_angle_beta                 74.1200(10)
_cell_angle_gamma                86.2530(10)
_cell_formula_units_Z            1
_cell_length_a                   7.2441(6)
_cell_length_b                   12.3260(10)
_cell_length_c                   12.3950(10)
_cell_measurement_reflns_used    3608
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.7
_cell_volume                     1034.39(15)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEXII (Bruker, 2004)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Bruker APEX-II 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  0.017
_diffrn_reflns_av_sigmaI/netI    0.027
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9651
_diffrn_reflns_theta_full        27.1
_diffrn_reflns_theta_max         27.1
_diffrn_reflns_theta_min         1.7
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Irregular block'
_exptl_crystal_F_000             434
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4495
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.047
_refine_ls_R_factor_gt           0.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0595P)²+0.185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.100
_refine_ls_wR_factor_ref         0.107
_reflns_number_gt                3822
_reflns_number_total             4495
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2145.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap and geom' was changed
to 'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        1034.5(2)
_cod_database_code               2210633
_cod_database_fobs_code          2210633
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.03490(10) Uani d S 1
O O1 0.5708(2) 0.47510(10) 0.35410(10) 0.0402(3) Uani d . 1
O O2 0.8370(3) 0.5232(2) -0.18330(10) 0.0681(5) Uani d D 1
O O3 0.8506(2) 0.17390(10) 0.53980(10) 0.0536(4) Uani d . 1
O O1W 0.9006(3) 0.3339(2) 0.33720(10) 0.0652(5) Uani d D 1
N N1 0.6373(2) 0.66330(10) 0.30300(10) 0.0399(4) Uani d . 1
N N2 0.5809(2) 0.64500(10) 0.42410(10) 0.0370(3) Uani d . 1
N N3 0.7667(3) 1.00030(10) 0.4428(2) 0.0481(4) Uani d D 1
N N4 0.8494(3) 0.2488(2) 0.6909(2) 0.0590(5) Uani d . 1
C C1 0.6833(3) 0.5601(2) 0.1543(2) 0.0386(4) Uani d . 1
C C2 0.6589(3) 0.4595(2) 0.1271(2) 0.0463(5) Uani d . 1
C C3 0.7124(3) 0.4491(2) 0.0142(2) 0.0541(5) Uani d . 1
C C4 0.7904(3) 0.5381(2) -0.0739(2) 0.0485(5) Uani d . 1
C C5 0.8148(3) 0.6392(2) -0.0486(2) 0.0526(5) Uani d . 1
C C6 0.7616(3) 0.6493(2) 0.0648(2) 0.0496(5) Uani d . 1
C C7 0.6279(3) 0.56830(10) 0.2759(2) 0.0366(4) Uani d . 1
C C8 0.5984(3) 0.72550(10) 0.4719(2) 0.0385(4) Uani d . 1
C C9 0.6632(3) 0.83870(10) 0.4276(2) 0.0385(4) Uani d . 1
C C10 0.7043(3) 0.8969(2) 0.5019(2) 0.0413(4) Uani d . 1
C C11 0.6951(3) 0.8610(2) 0.6272(2) 0.0544(5) Uani d . 1
C C12 0.7671(3) 1.0150(2) 0.3292(2) 0.0474(5) Uani d . 1
C C13 0.8188(4) 1.1089(2) 0.2393(2) 0.0674(7) Uani d . 1
C C14 0.8003(5) 1.1028(2) 0.1338(2) 0.0880(10) Uani d . 1
C C15 0.7319(5) 1.0061(2) 0.1179(2) 0.0863(10) Uani d . 1
C C16 0.6818(4) 0.9130(2) 0.2070(2) 0.0625(6) Uani d . 1
C C17 0.7015(3) 0.9149(2) 0.3149(2) 0.0438(4) Uani d . 1
C C18 0.8306(3) 0.1669(2) 0.6431(2) 0.0547(5) Uani d . 1
C C19 0.8989(4) 0.3612(2) 0.6225(2) 0.0692(7) Uani d . 1
C C20 0.8215(6) 0.2320(3) 0.8135(2) 0.1060(12) Uani d . 1
H H2o 0.910(4) 0.5731(18) -0.232(2) 0.088(10) Uiso d D 1
H H1w1 0.798(2) 0.371(2) 0.343(2) 0.069(8) Uiso d D 1
H H1w2 0.902(4) 0.293(2) 0.4020(10) 0.082(9) Uiso d D 1
H H3n 0.796(3) 1.048(2) 0.476(2) 0.066(7) Uiso d D 1
H H2 0.6059 0.3987 0.1857 0.056 Uiso calc R 1
H H3 0.6956 0.3813 -0.0024 0.065 Uiso calc R 1
H H5 0.8666 0.6999 -0.1076 0.063 Uiso calc R 1
H H6 0.7787 0.7172 0.0811 0.060 Uiso calc R 1
H H8 0.5609 0.7053 0.5520 0.046 Uiso calc R 1
H H11a 0.8227 0.8486 0.6363 0.082 Uiso calc R 1
H H11b 0.6225 0.7931 0.6601 0.082 Uiso calc R 1
H H11c 0.6341 0.9182 0.6656 0.082 Uiso calc R 1
H H13 0.8640 1.1731 0.2504 0.081 Uiso calc R 1
H H14 0.8339 1.1639 0.0719 0.106 Uiso calc R 1
H H15 0.7197 1.0043 0.0456 0.104 Uiso calc R 1
H H16 0.6353 0.8495 0.1949 0.075 Uiso calc R 1
H H18 0.7992 0.0971 0.6921 0.066 Uiso calc R 1
H H19a 0.9576 0.3585 0.5437 0.104 Uiso calc R 1
H H19b 0.9870 0.3933 0.6517 0.104 Uiso calc R 1
H H19c 0.7847 0.4060 0.6270 0.104 Uiso calc R 1
H H20a 0.7939 0.1548 0.8496 0.159 Uiso calc R 1
H H20b 0.7161 0.2771 0.8441 0.159 Uiso calc R 1
H H20c 0.9360 0.2530 0.8282 0.159 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'
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 N2 . . 83.52(6) yes
O1 Ni1 N2 . 2_666 96.48(6) yes
O1 Ni1 O1 . 2_666 180.0 ?
O1 Ni1 N2 2_666 2_666 83.52(6) ?
O1 Ni1 N2 2_666 . 96.48(6) ?
N2 Ni1 N2 2_666 . 180.0 ?
C7 O1 Ni1 . . 111.37(10) ?
C4 O2 H2o . . 114(2) ?
H1w1 O1W H1w2 . . 110(3) ?
C7 N1 N2 . . 108.06(14) ?
C8 N2 N1 . . 119.22(14) ?
C8 N2 Ni1 . . 126.36(12) ?
N1 N2 Ni1 . . 114.32(11) ?
C10 N3 C12 . . 110.12(16) ?
C10 N3 H3n . . 121.7(16) ?
C12 N3 H3n . . 128.2(16) ?
C18 N4 C20 . . 122.0(2) ?
C18 N4 C19 . . 121.52(19) ?
C20 N4 C19 . . 116.5(2) ?
C6 C1 C2 . . 118.08(17) ?
C6 C1 C7 . . 122.32(17) ?
C2 C1 C7 . . 119.60(16) ?
C3 C2 C1 . . 120.76(18) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C4 C3 C2 . . 120.65(19) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
O2 C4 C3 . . 117.86(19) ?
O2 C4 C5 . . 122.69(19) ?
C3 C4 C5 . . 119.43(18) ?
C6 C5 C4 . . 119.84(18) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C1 C6 C5 . . 121.24(18) ?
C1 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
N1 C7 O1 . . 122.54(16) ?
N1 C7 C1 . . 120.75(16) ?
O1 C7 C1 . . 116.71(15) ?
N2 C8 C9 . . 133.60(17) ?
N2 C8 H8 . . 113.2 ?
C9 C8 H8 . . 113.2 ?
C10 C9 C8 . . 119.01(16) ?
C10 C9 C17 . . 106.48(16) ?
C8 C9 C17 . . 134.51(17) ?
N3 C10 C9 . . 109.52(17) ?
N3 C10 C11 . . 119.78(17) ?
C9 C10 C11 . . 130.66(17) ?
C10 C11 H11a . . 109.5 ?
C10 C11 H11b . . 109.5 ?
H11a C11 H11b . . 109.5 ?
C10 C11 H11c . . 109.5 ?
H11a C11 H11c . . 109.5 ?
H11b C11 H11c . . 109.5 ?
N3 C12 C13 . . 129.01(19) ?
N3 C12 C17 . . 108.10(17) ?
C13 C12 C17 . . 122.9(2) ?
C14 C13 C12 . . 117.4(2) ?
C14 C13 H13 . . 121.3 ?
C12 C13 H13 . . 121.3 ?
C13 C14 C15 . . 120.9(2) ?
C13 C14 H14 . . 119.5 ?
C15 C14 H14 . . 119.5 ?
C16 C15 C14 . . 121.6(2) ?
C16 C15 H15 . . 119.2 ?
C14 C15 H15 . . 119.2 ?
C15 C16 C17 . . 119.4(2) ?
C15 C16 H16 . . 120.3 ?
C17 C16 H16 . . 120.3 ?
C16 C17 C12 . . 117.81(18) ?
C16 C17 C9 . . 136.35(18) ?
C12 C17 C9 . . 105.77(17) ?
O3 C18 N4 . . 126.3(2) ?
O3 C18 H18 . . 116.8 ?
N4 C18 H18 . . 116.8 ?
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 O1 . 1.8330(10) yes
Ni1 O1 2_666 1.8330(10) ?
Ni1 N2 2_666 1.8620(10) ?
Ni1 N2 . 1.8620(10) yes
O1 C7 . 1.322(2) ?
O2 C4 . 1.358(2) ?
O2 H2o . 0.850(10) ?
O3 C18 . 1.231(2) ?
O1W H1w1 . 0.840(10) ?
O1W H1w2 . 0.840(10) ?
N1 C7 . 1.302(2) ?
N1 N2 . 1.410(2) ?
N2 C8 . 1.299(2) ?
N3 C10 . 1.349(2) ?
N3 C12 . 1.376(3) ?
N3 H3n . 0.861(10) ?
N4 C18 . 1.316(3) ?
N4 C20 . 1.443(3) ?
N4 C19 . 1.453(3) ?
C1 C6 . 1.387(3) ?
C1 C2 . 1.394(3) ?
C1 C7 . 1.476(2) ?
C2 C3 . 1.381(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.375(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.388(3) ?
C5 C6 . 1.385(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C8 C9 . 1.432(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.394(3) ?
C9 C17 . 1.453(3) ?
C10 C11 . 1.494(3) ?
C11 H11a . 0.9600 ?
C11 H11b . 0.9600 ?
C11 H11c . 0.9600 ?
C12 C13 . 1.393(3) ?
C12 C17 . 1.416(3) ?
C13 C14 . 1.369(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.395(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.380(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.390(3) ?
C16 H16 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 H19a . 0.9600 ?
C19 H19b . 0.9600 ?
C19 H19c . 0.9600 ?
C20 H20a . 0.9600 ?
C20 H20b . 0.9600 ?
C20 H20c . 0.9600 ?
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
_geom_hbond_publ_flag
O2 H2o O1w 2_765 0.850(10) 1.850(10) 2.688(2) 171(3) yes
O1w H1w1 O1 . 0.840(10) 2.020(10) 2.852(2) 173(3) yes
O1w H1w2 O3 . 0.840(10) 1.940(10) 2.754(2) 163(3) yes
N3 H3n O3 1_565 0.860(10) 2.000(10) 2.859(2) 173(2) yes
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 O1 C7 2_666 176.52(12)
N2 Ni1 O1 C7 . -3.48(12)
C7 N1 N2 C8 . 172.68(17)
C7 N1 N2 Ni1 . -3.80(19)
O1 Ni1 N2 C8 . -172.04(17)
O1 Ni1 N2 C8 2_666 7.96(17)
O1 Ni1 N2 N1 . 4.15(12)
O1 Ni1 N2 N1 2_666 -175.85(12)
N2 Ni1 N2 N1 2_666 -6E1(10)
C6 C1 C2 C3 . 0.4(3)
C7 C1 C2 C3 . -178.95(19)
C1 C2 C3 C4 . -0.2(3)
C2 C3 C4 O2 . -178.8(2)
C2 C3 C4 C5 . -0.2(3)
O2 C4 C5 C6 . 179.0(2)
C3 C4 C5 C6 . 0.4(3)
C2 C1 C6 C5 . -0.2(3)
C7 C1 C6 C5 . 179.16(19)
C4 C5 C6 C1 . -0.2(4)
N2 N1 C7 O1 . 0.9(2)
N2 N1 C7 C1 . -178.49(15)
Ni1 O1 C7 N1 . 2.4(2)
Ni1 O1 C7 C1 . -178.19(13)
C6 C1 C7 N1 . 5.3(3)
C2 C1 C7 N1 . -175.40(18)
C6 C1 C7 O1 . -174.15(18)
C2 C1 C7 O1 . 5.2(3)
N1 N2 C8 C9 . 1.6(3)
Ni1 N2 C8 C9 . 177.63(17)
N2 C8 C9 C10 . -166.0(2)
N2 C8 C9 C17 . 13.5(4)
C12 N3 C10 C9 . 0.8(2)
C12 N3 C10 C11 . 178.84(19)
C8 C9 C10 N3 . 178.62(17)
C17 C9 C10 N3 . -1.1(2)
C8 C9 C10 C11 . 0.8(3)
C17 C9 C10 C11 . -178.9(2)
C10 N3 C12 C13 . 179.3(2)
C10 N3 C12 C17 . -0.1(2)
N3 C12 C13 C14 . -178.0(3)
C17 C12 C13 C14 . 1.3(4)
C12 C13 C14 C15 . 0.2(5)
C13 C14 C15 C16 . -0.5(6)
C14 C15 C16 C17 . -0.6(5)
C15 C16 C17 C12 . 2.0(4)
C15 C16 C17 C9 . 178.6(3)
N3 C12 C17 C16 . 177.0(2)
C13 C12 C17 C16 . -2.4(3)
N3 C12 C17 C9 . -0.5(2)
C13 C12 C17 C9 . -180.0(2)
C10 C9 C17 C16 . -175.9(3)
C8 C9 C17 C16 . 4.5(4)
C10 C9 C17 C12 . 1.0(2)
C8 C9 C17 C12 . -178.7(2)
C20 N4 C18 O3 . 179.6(3)
C19 N4 C18 O3 . -0.2(4)
