Download citation
Download citation
link to html
The title compound, [Ni(C14H10N3O4)2(C5H5N)2], contains a Ni atom (site symmetry 2) six-coordinated by two N,O-bidentate Schiff base ligands and two pyridine N atoms, giving a distorted trans-NiN4O2 octa­hedral coordination environment for the metal atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806014541/hb2036sup1.cif
Contains datablocks global, a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806014541/hb2036Isup2.hkl
Contains datablock I

CCDC reference: 610777

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.036
  • wR factor = 0.111
  • Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.95 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for N3 - C10 .. 5.49 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O1 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 O2 -NI1 -O2 -C7 -58.03 0.15 2.675 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis[(E)—N'-(2-nitrobenzylidene)-2-oxidobenzohydrazide]bis(pyridine- kN)nickel(II) top
Crystal data top
[Ni(C14H10N3O4)2(C5H5N)2]F(000) = 3248
Mr = 785.41Dx = 1.406 Mg m3
Orthorhombic, CccaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2b 2bcCell parameters from 3676 reflections
a = 14.9148 (2) Åθ = 4.2–26°
b = 22.1842 (4) ŵ = 0.59 mm1
c = 22.4259 (4) ÅT = 298 K
V = 7420.1 (2) Å3Block, green
Z = 80.46 × 0.24 × 0.13 mm
Data collection top
Bruker SMART APEX area-detector
diffractometer
4484 independent reflections
Radiation source: fine-focus sealed tube3308 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
ω scansθmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1916
Tmin = 0.841, Tmax = 0.925k = 2828
22385 measured reflectionsl = 2828
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0557P)2 + 3.9687P]
where P = (Fo2 + 2Fc2)/3
4484 reflections(Δ/σ)max = 0.001
249 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.43 e Å3
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
Ni10.75001.00000.846794 (13)0.04435 (11)
O20.84721 (8)0.93748 (5)0.84727 (5)0.0526 (3)
O11.08690 (12)0.98318 (10)0.93350 (8)0.0948 (6)
O30.91042 (16)1.18609 (10)0.91366 (12)0.1200 (8)
O40.8212 (2)1.24784 (11)0.87335 (14)0.1551 (11)
N10.92227 (10)1.00278 (7)0.90870 (6)0.0498 (3)
H10.97021.01330.92730.060*
N20.84214 (9)1.03529 (6)0.91118 (6)0.0459 (3)
N40.68284 (10)0.94826 (6)0.78115 (6)0.0504 (3)
N30.83677 (19)1.20626 (9)0.90609 (11)0.0917 (7)
C90.76532 (13)1.11916 (9)0.95617 (9)0.0563 (5)
C100.76022 (16)1.17881 (10)0.93819 (11)0.0724 (6)
C21.08082 (15)0.93539 (12)0.89681 (9)0.0727 (6)
C80.84489 (13)1.08056 (8)0.94592 (8)0.0540 (4)
H80.89821.08970.96540.065*
C150.68977 (15)0.88828 (9)0.78282 (10)0.0646 (5)
H150.72570.87100.81210.078*
C70.91669 (12)0.95442 (8)0.87488 (8)0.0479 (4)
C140.69242 (14)1.09590 (10)0.98708 (9)0.0651 (5)
H140.69381.05600.99990.078*
C170.59421 (17)0.87531 (11)0.69985 (11)0.0780 (6)
H170.56450.85080.67260.094*
C60.99904 (17)0.86759 (11)0.83315 (11)0.0792 (7)
H60.94570.85600.81500.095*
C120.6138 (2)1.18861 (14)0.97950 (15)0.1024 (10)
H120.56291.21160.98710.123*
C130.61808 (16)1.13063 (13)0.99920 (12)0.0840 (7)
H130.57071.11441.02090.101*
C160.64654 (17)0.85101 (10)0.74360 (12)0.0782 (6)
H160.65280.80940.74670.094*
C190.63146 (14)0.97157 (9)0.73851 (9)0.0612 (5)
H190.62551.01320.73640.073*
C31.15858 (17)0.90145 (16)0.88546 (13)0.1012 (10)
H31.21290.91300.90230.121*
C180.58667 (16)0.93667 (11)0.69731 (10)0.0763 (6)
H180.55160.95470.66800.092*
C41.1546 (2)0.85197 (17)0.84998 (13)0.1081 (12)
H41.20660.82990.84310.130*
C51.0759 (2)0.83382 (14)0.82408 (14)0.1044 (10)
H51.07410.79920.80070.125*
C110.6840 (2)1.21329 (12)0.94862 (14)0.0988 (9)
H110.68071.25270.93470.119*
C11.00073 (13)0.91859 (9)0.86897 (8)0.0569 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.04162 (18)0.04133 (17)0.05010 (19)0.00634 (12)0.0000.000
O20.0484 (7)0.0471 (6)0.0624 (7)0.0103 (5)0.0008 (6)0.0047 (5)
O10.0666 (10)0.1362 (16)0.0815 (11)0.0212 (10)0.0266 (9)0.0176 (11)
O30.0920 (15)0.0884 (14)0.179 (2)0.0015 (12)0.0286 (15)0.0190 (14)
O40.166 (2)0.1011 (15)0.198 (3)0.0332 (17)0.041 (2)0.0662 (18)
N10.0384 (7)0.0589 (9)0.0522 (8)0.0067 (6)0.0011 (6)0.0024 (7)
N20.0423 (7)0.0470 (7)0.0483 (8)0.0056 (6)0.0031 (6)0.0005 (6)
N40.0502 (8)0.0480 (8)0.0529 (8)0.0007 (6)0.0003 (7)0.0001 (6)
N30.1113 (19)0.0533 (11)0.1104 (18)0.0067 (12)0.0116 (14)0.0040 (11)
C90.0583 (11)0.0540 (10)0.0566 (10)0.0076 (8)0.0044 (9)0.0135 (8)
C100.0787 (15)0.0551 (11)0.0834 (15)0.0112 (10)0.0043 (12)0.0100 (11)
C20.0568 (12)0.1059 (18)0.0555 (11)0.0288 (12)0.0024 (9)0.0151 (12)
C80.0492 (10)0.0538 (10)0.0589 (10)0.0023 (8)0.0035 (8)0.0059 (8)
C150.0734 (13)0.0501 (10)0.0705 (12)0.0022 (9)0.0098 (11)0.0006 (9)
C70.0456 (9)0.0504 (9)0.0476 (9)0.0085 (7)0.0052 (7)0.0067 (7)
C140.0567 (11)0.0699 (12)0.0687 (13)0.0002 (9)0.0001 (10)0.0151 (10)
C170.0737 (15)0.0814 (15)0.0790 (15)0.0097 (12)0.0089 (12)0.0204 (12)
C60.0746 (15)0.0740 (14)0.0891 (16)0.0288 (12)0.0100 (13)0.0070 (12)
C120.0743 (17)0.104 (2)0.129 (2)0.0357 (16)0.0019 (17)0.0356 (19)
C130.0603 (13)0.0972 (18)0.0946 (17)0.0075 (12)0.0070 (13)0.0302 (15)
C160.0852 (16)0.0554 (11)0.0938 (17)0.0052 (11)0.0069 (14)0.0131 (12)
C190.0625 (12)0.0594 (11)0.0616 (12)0.0021 (9)0.0089 (9)0.0040 (9)
C30.0638 (15)0.160 (3)0.0797 (16)0.0499 (17)0.0036 (13)0.0149 (19)
C180.0730 (14)0.0883 (16)0.0677 (13)0.0000 (12)0.0182 (11)0.0007 (12)
C40.089 (2)0.146 (3)0.0889 (19)0.076 (2)0.0202 (16)0.0232 (19)
C50.106 (2)0.104 (2)0.103 (2)0.0581 (18)0.0188 (18)0.0071 (17)
C110.104 (2)0.0668 (14)0.125 (2)0.0329 (15)0.0009 (19)0.0123 (15)
C10.0535 (10)0.0660 (11)0.0511 (9)0.0195 (9)0.0083 (8)0.0114 (9)
Geometric parameters (Å, º) top
Ni1—O22.0064 (11)C15—H150.9300
Ni1—O2i2.0064 (11)C7—C11.490 (2)
Ni1—N42.1184 (15)C14—C131.377 (3)
Ni1—N4i2.1184 (15)C14—H140.9300
Ni1—N22.1416 (14)C17—C161.365 (3)
Ni1—N2i2.1416 (14)C17—C181.367 (3)
O2—C71.264 (2)C17—H170.9300
O1—C21.345 (3)C6—C51.384 (3)
O3—N31.198 (3)C6—C11.388 (3)
O4—N31.202 (3)C6—H60.9300
N1—C71.316 (2)C12—C131.361 (4)
N1—N21.3970 (19)C12—C111.369 (4)
N1—H10.8600C12—H120.9300
N2—C81.272 (2)C13—H130.9300
N4—C191.330 (2)C16—H160.9300
N4—C151.335 (2)C19—C181.378 (3)
N3—C101.481 (3)C19—H190.9300
C9—C101.386 (3)C3—C41.357 (5)
C9—C141.389 (3)C3—H30.9300
C9—C81.481 (3)C18—H180.9300
C10—C111.390 (3)C4—C51.371 (5)
C2—C11.398 (3)C4—H40.9300
C2—C31.406 (3)C5—H50.9300
C8—H80.9300C11—H110.9300
C15—C161.369 (3)
O2—Ni1—O2i179.39 (7)O2—C7—N1125.18 (15)
O2—Ni1—N488.33 (5)O2—C7—C1119.16 (16)
O2i—Ni1—N492.09 (5)N1—C7—C1115.65 (17)
O2—Ni1—N4i92.09 (5)C13—C14—C9121.4 (2)
O2i—Ni1—N4i88.33 (5)C13—C14—H14119.3
N4—Ni1—N4i91.96 (8)C9—C14—H14119.3
O2—Ni1—N277.61 (5)C16—C17—C18118.1 (2)
O2i—Ni1—N2101.97 (5)C16—C17—H17121.0
N4—Ni1—N2165.93 (5)C18—C17—H17121.0
N4i—Ni1—N288.11 (6)C5—C6—C1120.8 (3)
O2—Ni1—N2i101.97 (5)C5—C6—H6119.6
O2i—Ni1—N2i77.61 (5)C1—C6—H6119.6
N4—Ni1—N2i88.11 (6)C13—C12—C11120.4 (2)
N4i—Ni1—N2i165.93 (5)C13—C12—H12119.8
N2—Ni1—N2i95.21 (7)C11—C12—H12119.8
C7—O2—Ni1112.92 (10)C12—C13—C14120.1 (3)
C7—N1—N2112.93 (14)C12—C13—H13119.9
C7—N1—H1123.5C14—C13—H13119.9
N2—N1—H1123.5C17—C16—C15119.5 (2)
C8—N2—N1113.86 (15)C17—C16—H16120.2
C8—N2—Ni1136.26 (13)C15—C16—H16120.2
N1—N2—Ni1109.48 (10)N4—C19—C18122.9 (2)
C19—N4—C15116.88 (17)N4—C19—H19118.6
C19—N4—Ni1124.15 (13)C18—C19—H19118.6
C15—N4—Ni1118.94 (13)C4—C3—C2120.2 (3)
O3—N3—O4123.4 (3)C4—C3—H3119.9
O3—N3—C10119.0 (2)C2—C3—H3119.9
O4—N3—C10117.7 (3)C17—C18—C19119.4 (2)
C10—C9—C14117.19 (19)C17—C18—H18120.3
C10—C9—C8123.43 (19)C19—C18—H18120.3
C14—C9—C8119.34 (18)C3—C4—C5121.6 (2)
C9—C10—C11121.4 (2)C3—C4—H4119.2
C9—C10—N3119.46 (19)C5—C4—H4119.2
C11—C10—N3119.1 (2)C4—C5—C6119.2 (3)
O1—C2—C1122.73 (19)C4—C5—H5120.4
O1—C2—C3118.5 (2)C6—C5—H5120.4
C1—C2—C3118.8 (2)C12—C11—C10119.4 (3)
N2—C8—C9121.71 (17)C12—C11—H11120.3
N2—C8—H8119.1C10—C11—H11120.3
C9—C8—H8119.1C6—C1—C2119.43 (19)
N4—C15—C16123.2 (2)C6—C1—C7118.10 (19)
N4—C15—H15118.4C2—C1—C7122.45 (19)
C16—C15—H15118.4
O2i—Ni1—O2—C758.03 (15)C10—C9—C8—N2113.6 (2)
N4—Ni1—O2—C7167.91 (12)C14—C9—C8—N268.6 (3)
N4i—Ni1—O2—C776.01 (12)C19—N4—C15—C160.5 (3)
N2—Ni1—O2—C711.60 (12)Ni1—N4—C15—C16177.80 (19)
N2i—Ni1—O2—C7104.38 (12)Ni1—O2—C7—N111.0 (2)
C7—N1—N2—C8176.79 (16)Ni1—O2—C7—C1167.87 (12)
C7—N1—N2—Ni19.33 (16)N2—N1—C7—O20.5 (2)
O2—Ni1—N2—C8176.91 (19)N2—N1—C7—C1178.38 (14)
O2i—Ni1—N2—C82.64 (19)C10—C9—C14—C130.2 (3)
N4—Ni1—N2—C8178.9 (2)C8—C9—C14—C13178.1 (2)
N4i—Ni1—N2—C890.53 (18)C11—C12—C13—C141.4 (4)
N2i—Ni1—N2—C875.77 (18)C9—C14—C13—C121.7 (4)
O2—Ni1—N2—N111.19 (10)C18—C17—C16—C150.4 (4)
O2i—Ni1—N2—N1169.26 (10)N4—C15—C16—C170.8 (4)
N4—Ni1—N2—N19.2 (3)C15—N4—C19—C180.0 (3)
N4i—Ni1—N2—N181.37 (10)Ni1—N4—C19—C18178.25 (17)
N2i—Ni1—N2—N1112.33 (11)O1—C2—C3—C4178.2 (3)
O2—Ni1—N4—C19148.49 (16)C1—C2—C3—C42.6 (4)
O2i—Ni1—N4—C1931.95 (16)C16—C17—C18—C190.1 (4)
N4i—Ni1—N4—C1956.45 (14)N4—C19—C18—C170.3 (4)
N2—Ni1—N4—C19146.5 (2)C2—C3—C4—C50.4 (5)
N2i—Ni1—N4—C19109.47 (16)C3—C4—C5—C61.6 (5)
O2—Ni1—N4—C1533.33 (15)C1—C6—C5—C41.3 (4)
O2i—Ni1—N4—C15146.23 (15)C13—C12—C11—C100.8 (5)
N4i—Ni1—N4—C15125.37 (17)C9—C10—C11—C122.8 (4)
N2—Ni1—N4—C1535.3 (3)N3—C10—C11—C12178.5 (3)
N2i—Ni1—N4—C1568.70 (15)C5—C6—C1—C20.9 (4)
C14—C9—C10—C112.4 (3)C5—C6—C1—C7177.5 (2)
C8—C9—C10—C11179.8 (2)O1—C2—C1—C6178.0 (2)
C14—C9—C10—N3178.8 (2)C3—C2—C1—C62.8 (3)
C8—C9—C10—N31.0 (3)O1—C2—C1—C73.7 (3)
O3—N3—C10—C925.7 (4)C3—C2—C1—C7175.5 (2)
O4—N3—C10—C9154.0 (3)O2—C7—C1—C60.1 (3)
O3—N3—C10—C11155.6 (3)N1—C7—C1—C6179.12 (18)
O4—N3—C10—C1124.7 (4)O2—C7—C1—C2178.22 (17)
N1—N2—C8—C9177.64 (16)N1—C7—C1—C20.8 (3)
Ni1—N2—C8—C910.7 (3)
Symmetry code: (i) x+3/2, y+2, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds