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The title compound, [Ni(C18H12N4O2)], which was synthesized by reaction of N-[2-(picolinamido)phen­yl]picolinamide with Ni(NO3)2·6H2O in ethanol, is a mononuclear complex in which the nickel(II) ion is coordinated by four N atoms and displays a distorted square-planar coordination geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048386/bv2070sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048386/bv2070Isup2.hkl
Contains datablock I

CCDC reference: 1294088

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.045
  • wR factor = 0.119
  • Data-to-parameter ratio = 12.3

checkCIF/PLATON results

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Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - N1 .. 5.76 su PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (2) 1.95 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 234
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

As shown in Fig. 1, the title compound is a mononuclear complex in which each nickel(II) ion is coordinated by four N atoms from the same N-(2-(picolinamido)phenyl)picolinamide molecule and displays a distorted planar quadrilateral coordination geometry. The coordination bonds of Ni1—N are between 1.920 (4) Å and 2.016 (4) Å, atoms N1, N2, N3, and N4 are approximately coplanar with the central nickel(II) ion with a maximum deviation from the least squares plane of 0.0876 (2) Å for atom N1. Along the a axis, the benzene rings and pyridine rings of adjacent N-(2-(picolinamido)phenyl)picolinamide molecules are nearly parallel to each other impling there may exist π-π interactions between them. In the complex no classical hydrogen bonds are found and the three-dimensional network of the crystal is mainly consolidated by π-π interactions and weak interactions involving O atoms and the H atoms of adjacent pyridine rings.

Related literature top

For related literature, see: Liu et al. (2007).

Experimental top

A mixture of N-(2-(picolinamido)phenyl)picolinamide(0.314 g, 0.001 mol) and Ni(NO3)2.6H2O(0.288 g, 0.001 mol) was added to 20 ml e thanol, The mixture was closed in a steel tomb and heated at 418 K for 4 days, Single crystals suitable for X-ray diffraction analysis formed after it cooled down untouched in the air.

Refinement top

All H atoms were located at calculated positions and refined as riding on their parent C atoms with the C—H bond length fixed at 0.93Å with Uiso(H) = 1.2 times Ueq(C). In the final refinement cycles the anistropic parameters of atoms bonding to each other were constrained to be approximately equal.

Structure description top

As shown in Fig. 1, the title compound is a mononuclear complex in which each nickel(II) ion is coordinated by four N atoms from the same N-(2-(picolinamido)phenyl)picolinamide molecule and displays a distorted planar quadrilateral coordination geometry. The coordination bonds of Ni1—N are between 1.920 (4) Å and 2.016 (4) Å, atoms N1, N2, N3, and N4 are approximately coplanar with the central nickel(II) ion with a maximum deviation from the least squares plane of 0.0876 (2) Å for atom N1. Along the a axis, the benzene rings and pyridine rings of adjacent N-(2-(picolinamido)phenyl)picolinamide molecules are nearly parallel to each other impling there may exist π-π interactions between them. In the complex no classical hydrogen bonds are found and the three-dimensional network of the crystal is mainly consolidated by π-π interactions and weak interactions involving O atoms and the H atoms of adjacent pyridine rings.

For related literature, see: Liu et al. (2007).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures top
[Figure 1] Fig. 1. The molecular unit of (I), showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The packing diagram of (I), viewed along the c axis. Hydrogen bonds are shown as dashed lines.
[N,N'-(o-Phenylene)dipicolinamide-κ4N]nickel(II) top
Crystal data top
[Ni(C18H12N4O2)]F(000) = 768.0
Mr = 375.01Dx = 1.644 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6201 reflections
a = 7.052 (2) Åθ = 2.8–27.9°
b = 18.383 (5) ŵ = 1.30 mm1
c = 11.826 (3) ÅT = 293 K
β = 98.827 (4)°Block, blue
V = 1514.8 (7) Å30.31 × 0.27 × 0.22 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2784 independent reflections
Radiation source: fine-focus sealed tube2087 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 88
Tmin = 0.679, Tmax = 0.750k = 2222
9286 measured reflectionsl = 1414
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0623P)2 + 1.4239P]
where P = (Fo2 + 2Fc2)/3
2784 reflections(Δ/σ)max = 0.003
226 parametersΔρmax = 0.48 e Å3
234 restraintsΔρmin = 0.56 e Å3
Crystal data top
[Ni(C18H12N4O2)]V = 1514.8 (7) Å3
Mr = 375.01Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.052 (2) ŵ = 1.30 mm1
b = 18.383 (5) ÅT = 293 K
c = 11.826 (3) Å0.31 × 0.27 × 0.22 mm
β = 98.827 (4)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2784 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
2087 reflections with I > 2σ(I)
Tmin = 0.679, Tmax = 0.750Rint = 0.035
9286 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045234 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.00Δρmax = 0.48 e Å3
2784 reflectionsΔρmin = 0.56 e Å3
226 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.27023 (8)0.49353 (2)0.04659 (5)0.0392 (2)
N40.3749 (5)0.54985 (19)0.1888 (3)0.0491 (5)
C180.3852 (7)0.5336 (3)0.2993 (4)0.0525 (6)
H180.34900.48710.31890.063*
C170.4466 (7)0.5821 (2)0.3866 (4)0.0557 (6)
H170.45150.56860.46270.067*
C160.5004 (7)0.6508 (3)0.3581 (4)0.0562 (6)
H160.54120.68480.41480.067*
C150.4931 (7)0.6685 (3)0.2443 (4)0.0537 (6)
H150.53060.71440.22340.064*
C140.4297 (7)0.6176 (2)0.1617 (4)0.0496 (5)
C130.4132 (7)0.6356 (2)0.0369 (4)0.0492 (5)
C60.2871 (7)0.5805 (2)0.1482 (4)0.0479 (5)
C50.3207 (7)0.6352 (2)0.2235 (4)0.0513 (6)
H50.38750.67680.19590.062*
C40.2551 (7)0.6281 (3)0.3395 (4)0.0545 (6)
H40.27960.66470.38960.065*
C30.1537 (7)0.5672 (3)0.3814 (4)0.0556 (6)
H30.10780.56360.45920.067*
C20.1194 (7)0.5110 (2)0.3080 (4)0.0530 (6)
H20.05240.46970.33670.064*
C10.1860 (7)0.5172 (2)0.1916 (4)0.0487 (5)
C70.0884 (7)0.3988 (2)0.1232 (4)0.0508 (5)
C80.0954 (7)0.3593 (2)0.0110 (4)0.0509 (5)
C90.0197 (7)0.2900 (3)0.0066 (4)0.0548 (6)
H90.03860.26720.07310.066*
C100.0318 (7)0.2553 (2)0.0974 (4)0.0570 (6)
H100.01910.20890.10170.068*
C110.1188 (7)0.2894 (2)0.1942 (4)0.0554 (6)
H110.12890.26640.26490.067*
C120.1923 (7)0.3591 (2)0.1851 (4)0.0524 (6)
H120.25200.38230.25090.063*
N30.1797 (5)0.39376 (18)0.0844 (3)0.0492 (5)
N10.1611 (5)0.46607 (19)0.1063 (3)0.0477 (5)
N20.3430 (5)0.57963 (18)0.0291 (3)0.0467 (5)
O10.0220 (5)0.36873 (16)0.2133 (3)0.0565 (6)
O20.4605 (4)0.69673 (16)0.0071 (3)0.0542 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0475 (4)0.0257 (3)0.0445 (3)0.0000 (2)0.0071 (2)0.0003 (2)
N40.0594 (12)0.0381 (9)0.0502 (8)0.0017 (9)0.0098 (10)0.0048 (7)
C180.0640 (13)0.0437 (11)0.0501 (8)0.0017 (11)0.0093 (12)0.0053 (8)
C170.0667 (14)0.0470 (12)0.0532 (10)0.0011 (11)0.0087 (12)0.0080 (9)
C160.0660 (14)0.0458 (11)0.0566 (10)0.0014 (11)0.0085 (12)0.0101 (10)
C150.0625 (13)0.0408 (10)0.0578 (10)0.0023 (10)0.0088 (12)0.0086 (9)
C140.0584 (11)0.0359 (9)0.0549 (8)0.0023 (8)0.0095 (10)0.0059 (7)
C130.0583 (11)0.0329 (8)0.0569 (9)0.0038 (8)0.0101 (9)0.0018 (7)
C60.0558 (11)0.0379 (9)0.0507 (8)0.0020 (8)0.0108 (9)0.0026 (7)
C50.0587 (13)0.0433 (10)0.0528 (10)0.0032 (10)0.0117 (11)0.0052 (9)
C40.0617 (13)0.0495 (11)0.0530 (10)0.0045 (10)0.0113 (11)0.0056 (10)
C30.0625 (13)0.0521 (12)0.0525 (10)0.0041 (11)0.0095 (11)0.0028 (9)
C20.0598 (13)0.0480 (11)0.0514 (9)0.0028 (10)0.0089 (11)0.0007 (9)
C10.0559 (11)0.0408 (9)0.0499 (7)0.0020 (8)0.0095 (9)0.0012 (7)
C70.0559 (11)0.0366 (9)0.0601 (9)0.0029 (8)0.0097 (9)0.0076 (7)
C80.0544 (11)0.0338 (8)0.0656 (10)0.0025 (8)0.0129 (10)0.0034 (7)
C90.0577 (13)0.0363 (10)0.0717 (12)0.0031 (9)0.0139 (11)0.0023 (9)
C100.0599 (13)0.0378 (11)0.0748 (13)0.0027 (10)0.0155 (12)0.0026 (9)
C110.0595 (13)0.0372 (11)0.0714 (12)0.0016 (10)0.0158 (12)0.0065 (9)
C120.0573 (13)0.0353 (10)0.0664 (11)0.0011 (10)0.0151 (12)0.0063 (8)
N30.0540 (12)0.0323 (9)0.0629 (10)0.0015 (9)0.0136 (11)0.0020 (7)
N10.0549 (11)0.0367 (9)0.0518 (8)0.0018 (8)0.0090 (9)0.0044 (7)
N20.0562 (11)0.0325 (8)0.0519 (8)0.0019 (8)0.0098 (9)0.0012 (7)
O10.0618 (13)0.0426 (11)0.0642 (11)0.0040 (10)0.0072 (11)0.0110 (9)
O20.0641 (13)0.0352 (10)0.0633 (12)0.0068 (10)0.0101 (12)0.0001 (9)
Geometric parameters (Å, º) top
Ni1—N11.920 (4)C5—H50.9300
Ni1—N21.926 (3)C4—C31.378 (7)
Ni1—N42.016 (4)C4—H40.9300
Ni1—N32.015 (3)C3—C21.395 (6)
N4—C181.332 (6)C3—H30.9300
N4—C141.357 (5)C2—C11.389 (7)
C18—C171.382 (6)C2—H20.9300
C18—H180.9300C1—N11.409 (6)
C17—C161.374 (7)C7—O11.228 (5)
C17—H170.9300C7—N11.342 (5)
C16—C151.378 (7)C7—C81.506 (7)
C16—H160.9300C8—N31.350 (6)
C15—C141.375 (6)C8—C91.385 (6)
C15—H150.9300C9—C101.377 (6)
C14—C131.500 (6)C9—H90.9300
C13—O21.238 (5)C10—C111.365 (7)
C13—N21.339 (5)C10—H100.9300
C6—C51.388 (6)C11—C121.392 (6)
C6—N21.403 (6)C11—H110.9300
C6—C11.419 (6)C12—N31.341 (6)
C5—C41.386 (6)C12—H120.9300
N1—Ni1—N282.83 (15)C4—C3—C2120.6 (5)
N1—Ni1—N4164.32 (15)C4—C3—H3119.7
N2—Ni1—N482.89 (15)C2—C3—H3119.7
N1—Ni1—N382.82 (16)C1—C2—C3119.4 (5)
N2—Ni1—N3165.30 (16)C1—C2—H2120.3
N4—Ni1—N3111.72 (15)C3—C2—H2120.3
C18—N4—C14117.6 (4)C2—C1—N1126.5 (4)
C18—N4—Ni1131.4 (3)C2—C1—C6120.0 (4)
C14—N4—Ni1110.8 (3)N1—C1—C6113.4 (4)
N4—C18—C17123.4 (5)O1—C7—N1129.1 (5)
N4—C18—H18118.3O1—C7—C8120.3 (4)
C17—C18—H18118.3N1—C7—C8110.7 (4)
C18—C17—C16118.5 (5)N3—C8—C9121.5 (4)
C18—C17—H17120.8N3—C8—C7117.5 (4)
C16—C17—H17120.8C9—C8—C7121.1 (4)
C17—C16—C15119.1 (4)C10—C9—C8119.3 (5)
C17—C16—H16120.5C10—C9—H9120.4
C15—C16—H16120.5C8—C9—H9120.4
C14—C15—C16119.4 (4)C11—C10—C9119.6 (4)
C14—C15—H15120.3C11—C10—H10120.2
C16—C15—H15120.3C9—C10—H10120.2
N4—C14—C15122.0 (4)C10—C11—C12118.9 (5)
N4—C14—C13116.9 (4)C10—C11—H11120.6
C15—C14—C13121.1 (4)C12—C11—H11120.6
O2—C13—N2128.5 (4)N3—C12—C11122.1 (5)
O2—C13—C14119.7 (4)N3—C12—H12119.0
N2—C13—C14111.7 (4)C11—C12—H12119.0
C5—C6—N2127.0 (4)C12—N3—C8118.7 (4)
C5—C6—C1119.2 (4)C12—N3—Ni1130.5 (3)
N2—C6—C1113.7 (4)C8—N3—Ni1110.8 (3)
C6—C5—C4120.2 (5)C7—N1—C1126.5 (4)
C6—C5—H5119.9C7—N1—Ni1118.1 (3)
C4—C5—H5119.9C1—N1—Ni1115.0 (3)
C3—C4—C5120.5 (5)C13—N2—C6126.7 (4)
C3—C4—H4119.7C13—N2—Ni1117.5 (3)
C5—C4—H4119.7C6—N2—Ni1114.9 (3)

Experimental details

Crystal data
Chemical formula[Ni(C18H12N4O2)]
Mr375.01
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.052 (2), 18.383 (5), 11.826 (3)
β (°) 98.827 (4)
V3)1514.8 (7)
Z4
Radiation typeMo Kα
µ (mm1)1.30
Crystal size (mm)0.31 × 0.27 × 0.22
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.679, 0.750
No. of measured, independent and
observed [I > 2σ(I)] reflections
9286, 2784, 2087
Rint0.035
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.119, 1.00
No. of reflections2784
No. of parameters226
No. of restraints234
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.56

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

 

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