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The Ni atom in the title compound, [Ni(C19H14ClN4O)2]·2C2H6OS, which lies on a centre of inversion, is N,O-chelated by the two monoanionic ligands in a square-planar geometry. The asymmetric unit also contains a dimethyl sulfoxide solvent mol­ecule. The donor amino sites of the metal-bearing mol­ecule inter­act with the solvent mol­ecules to furnish a hydrogen-bonded layer structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056966/sj2417sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056966/sj2417Isup2.hkl
Contains datablock I

CCDC reference: 672669

Key indicators

  • Single-crystal X-ray study
  • T = 139 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.049
  • wR factor = 0.198
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.108 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8 PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... H1<I>N< PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... H4<I>N< PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C2 H6 O S
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (3) 2.96 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Related literature top

For the structure of 2'-[(5-chloro-1H-indol-3-yl)methylene]-2-(1H-indol-3-yl)acetohydrazide, see Ali et al. (2007).

Experimental top

2'-[(5-Chloro-1H-indol-3-yl)methylene]-2-(1H-indol-3-yl)acetohydrazide was synthesized by using a reported procedure (Ali et al., 2007). This compound (1 g, 2.85 mmol) and nickel acetate tetrahydrate (0.35 g, 1.42 mmol) were heated in ethanol (50 ml) for 5 h. The product that separated was collected and recrystallized from DMSO.

Refinement top

Carbon-bound H atoms were placed at calculated positions (C–H 0.95–0.99 Å), and were included in the refinement in the riding model approximation with U(H) set to 1.2–1.5Ueq(C). The amino hydrogen atom was located in a difference Fouier map, and was refined with a distance restraint of N–H 0.88±0.01 Å.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of (C19H14ClN4OS)2Ni.2DMSO. Displacement ellipsoids are drawn at the 50% probability level, and H atoms are shown as spheres of arbitrary radii. [Symmetry code (i): 1 – x, 1 – y, 1 – z.]
Bis{2'-[(5-chloro-1H-3-indolyl)methylene]-2-(1H-3- indolyl)acetohydrazido-κ2N,O}nickel(II) dimethyl sulfoxide disolvate top
Crystal data top
[Ni(C19H14ClN4O)2]·2C2H6OSF(000) = 948
Mr = 914.55Dx = 1.484 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1360 reflections
a = 11.659 (1) Åθ = 4.4–22.5°
b = 10.219 (1) ŵ = 0.76 mm1
c = 17.585 (2) ÅT = 139 K
β = 102.272 (3)°Block, red
V = 2047.2 (3) Å30.42 × 0.05 × 0.02 mm
Z = 2
Data collection top
Bruker APEXII CCD
diffractometer
4683 independent reflections
Radiation source: medium-focus sealed tube2216 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.108
ϕ and ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1514
Tmin = 0.776, Tmax = 0.985k = 1310
13220 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.076P)2]
where P = (Fo2 + 2Fc2)/3
4683 reflections(Δ/σ)max = 0.001
278 parametersΔρmax = 0.50 e Å3
2 restraintsΔρmin = 0.89 e Å3
Crystal data top
[Ni(C19H14ClN4O)2]·2C2H6OSV = 2047.2 (3) Å3
Mr = 914.55Z = 2
Monoclinic, P21/cMo Kα radiation
a = 11.659 (1) ŵ = 0.76 mm1
b = 10.219 (1) ÅT = 139 K
c = 17.585 (2) Å0.42 × 0.05 × 0.02 mm
β = 102.272 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
4683 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2216 reflections with I > 2σ(I)
Tmin = 0.776, Tmax = 0.985Rint = 0.108
13220 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0492 restraints
wR(F2) = 0.198H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.50 e Å3
4683 reflectionsΔρmin = 0.89 e Å3
278 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50000.50000.50000.0207 (3)
Cl10.77582 (14)0.23758 (13)0.53762 (9)0.0329 (4)
S10.21730 (14)0.18848 (14)0.10978 (9)0.0305 (4)
O10.3902 (3)0.5808 (3)0.4234 (2)0.0240 (9)
O20.2384 (3)0.0989 (4)0.1797 (2)0.0315 (10)
N10.4210 (4)0.0021 (5)0.2925 (3)0.0263 (11)
H1N0.369 (4)0.029 (6)0.252 (2)0.05 (2)*
N20.4846 (4)0.3641 (4)0.4281 (3)0.0214 (10)
N30.4110 (4)0.3933 (4)0.3554 (3)0.0242 (11)
N40.0266 (5)0.5368 (5)0.3064 (3)0.0289 (12)
H4N0.096 (2)0.499 (5)0.297 (4)0.040 (19)*
C10.5565 (5)0.0105 (5)0.4043 (3)0.0207 (12)
C20.6428 (5)0.0401 (5)0.4652 (3)0.0230 (13)
H20.67870.01310.50790.028*
C30.6737 (5)0.1689 (5)0.4610 (3)0.0262 (14)
C40.6230 (5)0.2500 (5)0.3983 (3)0.0276 (14)
H40.64740.33860.39760.033*
C50.5385 (5)0.2023 (5)0.3380 (3)0.0276 (14)
H50.50410.25600.29500.033*
C60.5055 (5)0.0719 (5)0.3425 (3)0.0230 (13)
C70.4171 (5)0.1210 (5)0.3197 (3)0.0240 (13)
H70.36570.18770.29500.029*
C80.4989 (5)0.1359 (5)0.3887 (3)0.0237 (13)
C90.5233 (5)0.2449 (5)0.4401 (3)0.0226 (13)
H90.57390.22850.48910.027*
C100.3674 (5)0.5089 (5)0.3609 (3)0.0223 (12)
C110.2836 (5)0.5632 (5)0.2906 (3)0.0243 (13)
H11A0.31270.64950.27740.029*
H11B0.28200.50410.24580.029*
C120.1612 (5)0.5787 (5)0.3033 (3)0.0224 (13)
C130.0737 (5)0.4888 (5)0.2867 (3)0.0252 (13)
H130.08060.40490.26480.030*
C140.1126 (5)0.6907 (5)0.3346 (3)0.0211 (12)
C150.1571 (5)0.8133 (5)0.3635 (3)0.0267 (14)
H150.23510.83790.36200.032*
C160.0856 (6)0.8971 (6)0.3938 (3)0.0331 (16)
H160.11520.97990.41340.040*
C170.0294 (6)0.8624 (5)0.3964 (3)0.0315 (15)
H170.07610.92120.41870.038*
C180.0766 (6)0.7439 (5)0.3671 (3)0.0291 (14)
H180.15540.72080.36750.035*
C190.0038 (5)0.6605 (5)0.3371 (3)0.0233 (13)
C200.1682 (6)0.0854 (6)0.0285 (4)0.0445 (18)
H20A0.23450.03450.01820.067*
H20B0.10800.02570.03960.067*
H20C0.13490.13880.01710.067*
C210.0809 (6)0.2677 (6)0.1102 (4)0.0408 (17)
H21A0.08880.32140.15720.061*
H21B0.05930.32360.06410.061*
H21C0.01980.20170.10950.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0197 (6)0.0166 (5)0.0232 (6)0.0004 (4)0.0016 (4)0.0016 (4)
Cl10.0278 (9)0.0262 (8)0.0419 (9)0.0053 (6)0.0011 (7)0.0021 (6)
S10.0267 (9)0.0282 (8)0.0343 (9)0.0030 (7)0.0017 (7)0.0093 (7)
O10.024 (2)0.0199 (19)0.025 (2)0.0006 (17)0.0017 (18)0.0009 (16)
O20.023 (2)0.037 (2)0.029 (2)0.0041 (19)0.0044 (19)0.0139 (18)
N10.026 (3)0.026 (3)0.024 (3)0.004 (2)0.002 (2)0.007 (2)
N20.016 (3)0.023 (2)0.025 (3)0.002 (2)0.003 (2)0.0009 (19)
N30.025 (3)0.021 (2)0.023 (3)0.001 (2)0.003 (2)0.0013 (19)
N40.023 (3)0.027 (3)0.036 (3)0.006 (2)0.002 (2)0.001 (2)
C10.019 (3)0.018 (3)0.025 (3)0.004 (2)0.004 (2)0.005 (2)
C20.018 (3)0.025 (3)0.025 (3)0.005 (2)0.000 (3)0.005 (2)
C30.023 (3)0.023 (3)0.033 (3)0.000 (2)0.006 (3)0.001 (2)
C40.028 (4)0.017 (3)0.041 (4)0.001 (3)0.013 (3)0.006 (3)
C50.024 (3)0.025 (3)0.033 (3)0.009 (3)0.005 (3)0.010 (3)
C60.015 (3)0.027 (3)0.024 (3)0.004 (2)0.001 (3)0.000 (2)
C70.026 (3)0.022 (3)0.023 (3)0.006 (2)0.001 (3)0.001 (2)
C80.025 (3)0.021 (3)0.023 (3)0.002 (2)0.001 (3)0.004 (2)
C90.022 (3)0.019 (3)0.025 (3)0.002 (2)0.003 (3)0.000 (2)
C100.017 (3)0.027 (3)0.021 (3)0.004 (2)0.001 (2)0.002 (2)
C110.024 (3)0.025 (3)0.021 (3)0.003 (3)0.003 (3)0.000 (2)
C120.023 (3)0.022 (3)0.019 (3)0.000 (2)0.002 (3)0.004 (2)
C130.023 (3)0.024 (3)0.027 (3)0.001 (3)0.002 (3)0.002 (2)
C140.021 (3)0.021 (3)0.018 (3)0.002 (2)0.001 (2)0.005 (2)
C150.026 (3)0.024 (3)0.026 (3)0.003 (3)0.003 (3)0.004 (2)
C160.041 (4)0.022 (3)0.032 (4)0.002 (3)0.002 (3)0.001 (3)
C170.034 (4)0.028 (3)0.033 (4)0.010 (3)0.007 (3)0.003 (3)
C180.024 (3)0.031 (3)0.031 (3)0.002 (3)0.003 (3)0.007 (3)
C190.026 (3)0.020 (3)0.022 (3)0.002 (2)0.001 (3)0.006 (2)
C200.058 (5)0.044 (4)0.030 (4)0.012 (4)0.007 (4)0.003 (3)
C210.042 (4)0.040 (4)0.036 (4)0.017 (3)0.001 (3)0.001 (3)
Geometric parameters (Å, º) top
Ni1—O11.845 (4)C7—C81.382 (7)
Ni1—O1i1.845 (4)C7—H70.9500
Ni1—N2i1.861 (4)C8—C91.425 (7)
Ni1—N21.861 (4)C9—H90.9500
Cl1—C31.745 (6)C10—C111.510 (7)
S1—O21.510 (4)C11—C121.499 (8)
S1—C201.769 (6)C11—H11A0.9900
S1—C211.786 (6)C11—H11B0.9900
O1—C101.301 (6)C12—C131.358 (7)
N1—C71.351 (6)C12—C141.438 (7)
N1—C61.372 (7)C13—H130.9500
N1—H1N0.88 (4)C14—C191.402 (8)
N2—C91.300 (6)C14—C151.408 (7)
N2—N31.413 (6)C15—C161.379 (8)
N3—C101.297 (6)C15—H150.9500
N4—C191.378 (7)C16—C171.398 (8)
N4—C131.378 (7)C16—H160.9500
N4—H4N0.88 (3)C17—C181.383 (8)
C1—C21.403 (7)C17—H170.9500
C1—C61.403 (7)C18—C191.384 (8)
C1—C81.446 (7)C18—H180.9500
C2—C31.370 (7)C20—H20A0.9800
C2—H20.9500C20—H20B0.9800
C3—C41.405 (8)C20—H20C0.9800
C4—C51.374 (8)C21—H21A0.9800
C4—H40.9500C21—H21B0.9800
C5—C61.395 (7)C21—H21C0.9800
C5—H50.9500
O1—Ni1—O1i180.000 (1)C8—C9—H9116.1
O1—Ni1—N2i96.52 (17)N3—C10—O1124.4 (5)
O1i—Ni1—N2i83.48 (17)N3—C10—C11118.0 (5)
O1—Ni1—N283.48 (17)O1—C10—C11117.6 (5)
O1i—Ni1—N296.52 (17)C12—C11—C10112.9 (5)
N2i—Ni1—N2180.000 (1)C12—C11—H11A109.0
O2—S1—C20105.4 (3)C10—C11—H11A109.0
O2—S1—C21105.2 (3)C12—C11—H11B109.0
C20—S1—C2197.9 (3)C10—C11—H11B109.0
C10—O1—Ni1110.4 (3)H11A—C11—H11B107.8
C7—N1—C6109.3 (5)C13—C12—C14106.4 (5)
C7—N1—H1N121 (4)C13—C12—C11126.3 (5)
C6—N1—H1N129 (4)C14—C12—C11127.3 (5)
C9—N2—N3117.9 (4)C12—C13—N4110.1 (5)
C9—N2—Ni1127.5 (4)C12—C13—H13124.9
N3—N2—Ni1114.2 (3)N4—C13—H13124.9
C10—N3—N2107.2 (4)C19—C14—C15118.0 (5)
C19—N4—C13108.8 (5)C19—C14—C12107.4 (5)
C19—N4—H4N125 (4)C15—C14—C12134.6 (5)
C13—N4—H4N126 (4)C16—C15—C14119.1 (6)
C2—C1—C6119.1 (5)C16—C15—H15120.5
C2—C1—C8134.5 (5)C14—C15—H15120.5
C6—C1—C8106.3 (5)C15—C16—C17121.2 (6)
C3—C2—C1117.8 (5)C15—C16—H16119.4
C3—C2—H2121.1C17—C16—H16119.4
C1—C2—H2121.1C18—C17—C16121.2 (6)
C2—C3—C4122.5 (5)C18—C17—H17119.4
C2—C3—Cl1119.3 (4)C16—C17—H17119.4
C4—C3—Cl1118.2 (4)C17—C18—C19117.0 (6)
C5—C4—C3120.6 (5)C17—C18—H18121.5
C5—C4—H4119.7C19—C18—H18121.5
C3—C4—H4119.7N4—C19—C18129.2 (6)
C4—C5—C6117.1 (5)N4—C19—C14107.3 (5)
C4—C5—H5121.4C18—C19—C14123.5 (5)
C6—C5—H5121.4S1—C20—H20A109.5
N1—C6—C5129.0 (5)S1—C20—H20B109.5
N1—C6—C1108.2 (5)H20A—C20—H20B109.5
C5—C6—C1122.8 (5)S1—C20—H20C109.5
N1—C7—C8110.2 (5)H20A—C20—H20C109.5
N1—C7—H7124.9H20B—C20—H20C109.5
C8—C7—H7124.9S1—C21—H21A109.5
C7—C8—C9130.6 (5)S1—C21—H21B109.5
C7—C8—C1105.9 (5)H21A—C21—H21B109.5
C9—C8—C1123.4 (5)S1—C21—H21C109.5
N2—C9—C8127.8 (5)H21A—C21—H21C109.5
N2—C9—H9116.1H21B—C21—H21C109.5
N2i—Ni1—O1—C10175.5 (4)Ni1—N2—C9—C8170.9 (5)
N2—Ni1—O1—C104.5 (4)C7—C8—C9—N210.9 (11)
O1—Ni1—N2—C9167.7 (5)C1—C8—C9—N2173.1 (6)
O1i—Ni1—N2—C912.3 (5)N2—N3—C10—O10.0 (7)
O1—Ni1—N2—N34.7 (3)N2—N3—C10—C11179.2 (4)
O1i—Ni1—N2—N3175.3 (3)Ni1—O1—C10—N33.8 (7)
C9—N2—N3—C10169.3 (5)Ni1—O1—C10—C11177.0 (4)
Ni1—N2—N3—C103.8 (5)N3—C10—C11—C12113.6 (6)
C6—C1—C2—C30.3 (8)O1—C10—C11—C1265.7 (6)
C8—C1—C2—C3177.8 (6)C10—C11—C12—C1391.7 (7)
C1—C2—C3—C40.5 (9)C10—C11—C12—C1488.7 (7)
C1—C2—C3—Cl1177.1 (4)C14—C12—C13—N40.6 (6)
C2—C3—C4—C50.4 (9)C11—C12—C13—N4179.8 (5)
Cl1—C3—C4—C5177.3 (5)C19—N4—C13—C120.5 (6)
C3—C4—C5—C60.6 (9)C13—C12—C14—C191.4 (6)
C7—N1—C6—C5179.2 (6)C11—C12—C14—C19178.9 (5)
C7—N1—C6—C10.5 (7)C13—C12—C14—C15178.9 (6)
C4—C5—C6—N1177.1 (6)C11—C12—C14—C151.4 (10)
C4—C5—C6—C11.4 (9)C19—C14—C15—C161.0 (8)
C2—C1—C6—N1177.5 (5)C12—C14—C15—C16176.3 (6)
C8—C1—C6—N10.7 (6)C14—C15—C16—C170.0 (8)
C2—C1—C6—C51.3 (9)C15—C16—C17—C181.4 (9)
C8—C1—C6—C5179.4 (5)C16—C17—C18—C191.6 (8)
C6—N1—C7—C80.2 (7)C13—N4—C19—C18177.5 (5)
N1—C7—C8—C9176.8 (6)C13—N4—C19—C141.4 (6)
N1—C7—C8—C10.2 (7)C17—C18—C19—N4178.2 (5)
C2—C1—C8—C7177.2 (6)C17—C18—C19—C140.5 (8)
C6—C1—C8—C70.6 (6)C15—C14—C19—N4179.7 (5)
C2—C1—C8—C90.3 (10)C12—C14—C19—N41.7 (6)
C6—C1—C8—C9177.4 (5)C15—C14—C19—C180.8 (8)
N3—N2—C9—C81.3 (9)C12—C14—C19—C18177.3 (5)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O20.88 (4)1.90 (5)2.766 (6)167 (6)
N4—H4N···O2ii0.88 (3)2.05 (3)2.887 (6)158 (6)
Symmetry code: (ii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Ni(C19H14ClN4O)2]·2C2H6OS
Mr914.55
Crystal system, space groupMonoclinic, P21/c
Temperature (K)139
a, b, c (Å)11.659 (1), 10.219 (1), 17.585 (2)
β (°) 102.272 (3)
V3)2047.2 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.76
Crystal size (mm)0.42 × 0.05 × 0.02
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.776, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
13220, 4683, 2216
Rint0.108
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.198, 0.99
No. of reflections4683
No. of parameters278
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.50, 0.89

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).

Selected bond lengths (Å) top
Ni1—O11.845 (4)Ni1—N21.861 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O20.88 (4)1.90 (5)2.766 (6)167 (6)
N4—H4N···O2i0.88 (3)2.05 (3)2.887 (6)158 (6)
Symmetry code: (i) x, y+1/2, z+1/2.
 

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