Download citation
Download citation
link to html
In the title complex, [Ni(C12H14N3O3)(C2H3O2)(C5H5N)2], the NiII atom is six-coordinated by two N atoms and one O atom from a tridentate hydrazone ligand, two N atoms from two pyridine molecules, and one O atom from an acetate group, leading to a distorted octahedral geometry. The two N atoms of the pyridine molecules occupy the axial sites and the other four coordinated atoms define the equatorial plane. The uncoordinated acetate O atom forms an intramolecular hydrogen bond with the oxime O atom of the hydrazone ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804033495/kp6029sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804033495/kp6029Isup2.hkl
Contains datablock I

CCDC reference: 262273

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.041
  • wR factor = 0.104
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C6 - C7 .. 5.20 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(Acetato-κO)[diacetyl monooxime (4-methoxybenzoyl)hydrazonato- κ3O,N,N']bis(pyridine-κN)nickel(II) top
Crystal data top
[Ni(C12H14N3O3)(C2H3O2)(C5H5N)2]Z = 2
Mr = 524.20F(000) = 548
Triclinic, P1Dx = 1.400 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1027 (16) ÅCell parameters from 10312 reflections
b = 12.668 (3) Åθ = 3.0–27.4°
c = 13.436 (3) ŵ = 0.82 mm1
α = 110.74 (3)°T = 296 K
β = 92.41 (3)°Prism, brown
γ = 103.37 (3)°0.34 × 0.25 × 0.13 mm
V = 1243.1 (6) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5635 independent reflections
Radiation source: fine-focus sealed tube4089 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 10 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scanh = 1010
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1616
Tmin = 0.767, Tmax = 0.900l = 1717
12322 measured reflections
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0535P)2 + 0.0609P]
where P = (Fo2 + 2Fc2)/3
5635 reflections(Δ/σ)max = 0.001
323 parametersΔρmax = 0.28 e Å3
1 restraintΔρmin = 0.21 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.20474 (4)0.64634 (3)0.32097 (2)0.04187 (11)
N10.3677 (3)0.60966 (18)0.20229 (14)0.0480 (5)
N20.4297 (2)0.75760 (17)0.39396 (14)0.0420 (4)
N30.4449 (2)0.82680 (18)0.50125 (14)0.0446 (4)
N40.1469 (2)0.76983 (18)0.25929 (15)0.0462 (5)
N50.2551 (2)0.51253 (18)0.37233 (14)0.0466 (5)
O10.3282 (2)0.52721 (18)0.09877 (13)0.0626 (5)
O20.15253 (19)0.73611 (14)0.47367 (11)0.0459 (4)
O30.2455 (3)1.0180 (2)0.97390 (14)0.0811 (6)
O40.0331 (2)0.54286 (16)0.25803 (13)0.0535 (4)
O50.0240 (3)0.4201 (2)0.10706 (16)0.0815 (6)
C10.6549 (4)0.6686 (3)0.1552 (2)0.0686 (8)
C20.5226 (3)0.6763 (2)0.22897 (18)0.0479 (6)
C30.5610 (3)0.7611 (2)0.34145 (18)0.0458 (5)
C40.7356 (3)0.8382 (3)0.3877 (2)0.0652 (7)
C50.2897 (3)0.8044 (2)0.53332 (17)0.0414 (5)
C60.2833 (3)0.8640 (2)0.64942 (17)0.0418 (5)
C70.1518 (3)0.8179 (2)0.69751 (18)0.0504 (6)
C80.1456 (3)0.8704 (2)0.80595 (19)0.0563 (6)
C90.2682 (3)0.9725 (2)0.86799 (18)0.0547 (6)
C100.3972 (3)1.0195 (3)0.8217 (2)0.0606 (7)
C110.4066 (3)0.9653 (2)0.71324 (19)0.0543 (6)
C120.3600 (5)1.1284 (3)1.0389 (2)0.1004 (13)
C130.1593 (3)0.8807 (2)0.3211 (2)0.0521 (6)
C140.1337 (4)0.9628 (3)0.2818 (2)0.0632 (7)
C150.0955 (4)0.9289 (3)0.1716 (2)0.0639 (7)
C160.0827 (4)0.8161 (3)0.1074 (2)0.0623 (7)
C170.1076 (3)0.7386 (2)0.15243 (19)0.0533 (6)
C180.2116 (3)0.5068 (2)0.46464 (19)0.0543 (6)
C190.2395 (4)0.4231 (3)0.5023 (2)0.0636 (7)
C200.3211 (3)0.3433 (3)0.4429 (2)0.0622 (7)
C210.3650 (4)0.3470 (3)0.3480 (2)0.0675 (7)
C220.3311 (4)0.4316 (3)0.3151 (2)0.0635 (7)
C230.0743 (3)0.4543 (2)0.1725 (2)0.0554 (6)
C240.2598 (4)0.3834 (3)0.1477 (3)0.0768 (9)
H1A0.74630.64530.18220.103*
H1B0.69930.74370.15060.103*
H1C0.60460.61200.08510.103*
H4A0.73240.89370.45770.098*
H4B0.77650.87900.34190.098*
H4C0.81100.79160.39350.098*
H70.06700.75090.65610.060*
H80.05890.83740.83760.068*
H100.47911.08820.86300.073*
H110.49650.99700.68280.065*
H12A0.47471.12031.04350.151*
H12B0.32731.15421.10960.151*
H12C0.35501.18481.00720.151*
H130.18680.90370.39490.063*
H140.14181.03910.32780.076*
H150.07900.98250.14200.077*
H160.05710.79170.03330.075*
H170.09700.66150.10770.064*
H180.15940.56220.50650.065*
H190.20360.42110.56660.076*
H200.34580.28780.46730.075*
H210.41780.29250.30520.081*
H220.36240.43280.24960.076*
H24A0.31130.39990.21270.115*
H24B0.26520.30150.11740.115*
H24C0.32050.40380.09730.115*
H250.2236 (18)0.490 (3)0.089 (3)0.094*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.03947 (17)0.04536 (19)0.03871 (16)0.01130 (13)0.00858 (11)0.01287 (12)
N10.0562 (12)0.0521 (13)0.0391 (9)0.0218 (10)0.0149 (8)0.0154 (8)
N20.0416 (10)0.0455 (12)0.0411 (9)0.0136 (8)0.0098 (7)0.0171 (8)
N30.0413 (10)0.0471 (12)0.0436 (10)0.0105 (9)0.0090 (8)0.0152 (8)
N40.0386 (10)0.0501 (13)0.0507 (11)0.0128 (9)0.0077 (8)0.0188 (9)
N50.0426 (10)0.0481 (12)0.0466 (10)0.0100 (9)0.0062 (8)0.0161 (9)
O10.0694 (12)0.0670 (13)0.0412 (9)0.0194 (10)0.0145 (8)0.0065 (8)
O20.0366 (8)0.0516 (10)0.0410 (8)0.0063 (7)0.0088 (6)0.0101 (7)
O30.0979 (16)0.0849 (16)0.0392 (9)0.0066 (13)0.0120 (10)0.0090 (9)
O40.0448 (9)0.0523 (11)0.0551 (10)0.0056 (8)0.0027 (7)0.0153 (8)
O50.0706 (13)0.0749 (15)0.0659 (12)0.0008 (11)0.0138 (10)0.0014 (10)
C10.0692 (18)0.077 (2)0.0697 (17)0.0273 (16)0.0379 (14)0.0307 (15)
C20.0466 (13)0.0557 (16)0.0519 (13)0.0211 (12)0.0179 (10)0.0266 (11)
C30.0400 (12)0.0501 (15)0.0548 (13)0.0152 (10)0.0141 (10)0.0254 (11)
C40.0452 (14)0.080 (2)0.0677 (16)0.0032 (13)0.0137 (12)0.0321 (15)
C50.0428 (12)0.0410 (13)0.0421 (11)0.0140 (10)0.0080 (9)0.0154 (9)
C60.0387 (11)0.0447 (14)0.0437 (11)0.0128 (10)0.0078 (9)0.0170 (9)
C70.0500 (13)0.0491 (15)0.0444 (12)0.0091 (11)0.0069 (10)0.0109 (10)
C80.0563 (15)0.0596 (17)0.0503 (13)0.0089 (13)0.0146 (11)0.0206 (12)
C90.0610 (16)0.0610 (17)0.0382 (12)0.0162 (13)0.0048 (11)0.0143 (11)
C100.0544 (15)0.0571 (17)0.0516 (14)0.0007 (13)0.0012 (11)0.0079 (12)
C110.0495 (14)0.0561 (16)0.0488 (13)0.0066 (12)0.0070 (10)0.0141 (11)
C120.134 (3)0.088 (3)0.0431 (16)0.004 (2)0.0046 (18)0.0011 (15)
C130.0499 (14)0.0510 (16)0.0525 (13)0.0124 (12)0.0063 (10)0.0164 (11)
C140.0657 (17)0.0470 (16)0.0783 (19)0.0158 (13)0.0150 (14)0.0240 (14)
C150.0591 (16)0.067 (2)0.0814 (19)0.0197 (14)0.0142 (14)0.0446 (16)
C160.0648 (16)0.074 (2)0.0576 (15)0.0236 (15)0.0099 (12)0.0323 (15)
C170.0532 (14)0.0559 (16)0.0495 (13)0.0154 (12)0.0065 (11)0.0177 (11)
C180.0563 (15)0.0545 (16)0.0540 (14)0.0125 (12)0.0156 (11)0.0228 (12)
C190.0702 (18)0.0654 (19)0.0582 (15)0.0112 (15)0.0095 (13)0.0306 (14)
C200.0572 (15)0.0594 (18)0.0743 (18)0.0094 (14)0.0051 (13)0.0355 (15)
C210.078 (2)0.0622 (19)0.0729 (18)0.0330 (16)0.0176 (15)0.0282 (15)
C220.083 (2)0.0613 (18)0.0554 (15)0.0311 (16)0.0206 (13)0.0239 (13)
C230.0577 (15)0.0483 (16)0.0528 (14)0.0065 (12)0.0020 (12)0.0158 (12)
C240.0600 (17)0.063 (2)0.087 (2)0.0032 (15)0.0000 (15)0.0175 (16)
Geometric parameters (Å, º) top
Ni1—N21.988 (2)C7—C81.380 (3)
Ni1—O42.0144 (18)C7—H70.9300
Ni1—O22.0794 (16)C8—C91.388 (4)
Ni1—N12.107 (2)C8—H80.9300
Ni1—N42.140 (2)C9—C101.366 (4)
Ni1—N52.154 (2)C10—C111.388 (3)
N1—C21.294 (3)C10—H100.9300
N2—C31.302 (3)C11—H110.9300
N2—N31.379 (3)C12—H12A0.9600
N3—C51.347 (3)C12—H12B0.9600
O1—N11.381 (3)C12—H12C0.9600
O2—C51.271 (3)C13—C141.373 (4)
N4—C131.331 (3)C13—H130.9300
N4—C171.349 (3)C14—C151.387 (4)
N5—C181.325 (3)C14—H140.9300
N5—C221.340 (3)C15—C161.359 (4)
O1—H250.85 (3)C15—H150.9300
O3—C91.372 (3)C16—C171.368 (4)
O3—C121.431 (4)C16—H160.9300
O4—C231.254 (3)C17—H170.9300
O5—C231.242 (3)C18—C191.383 (4)
C1—C21.487 (3)C18—H180.9300
C1—H1A0.9600C19—C201.371 (4)
C1—H1B0.9600C19—H190.9300
C1—H1C0.9600C20—C211.352 (4)
C2—C31.480 (3)C20—H200.9300
C3—C41.483 (3)C21—C221.371 (4)
C4—H4A0.9600C21—H210.9300
C4—H4B0.9600C22—H220.9300
C4—H4C0.9600C23—C241.517 (4)
C5—C61.482 (3)C24—H24A0.9600
C6—C71.390 (3)C24—H24B0.9600
C6—C111.391 (3)C24—H24C0.9600
N1—Ni1—N487.34 (8)C7—C8—C9120.2 (2)
N1—Ni1—N590.85 (8)C7—C8—H8119.9
N2—Ni1—N176.48 (8)C8—C7—C6120.7 (2)
N2—Ni1—N490.22 (8)C8—C7—H7119.6
N2—Ni1—N592.84 (8)C9—O3—C12116.7 (2)
N2—Ni1—O276.81 (7)C9—C8—H8119.9
N2—Ni1—O4174.67 (7)C9—C10—C11120.2 (2)
N4—Ni1—N5175.99 (7)C9—C10—H10119.9
O2—Ni1—N1153.30 (8)C10—C9—O3125.5 (2)
O2—Ni1—N492.89 (7)C10—C9—C8119.7 (2)
O2—Ni1—N590.34 (7)C10—C11—C6120.8 (2)
O4—Ni1—N1108.63 (8)C10—C11—H11119.6
O4—Ni1—N488.55 (8)C11—C6—C5122.0 (2)
O4—Ni1—N588.64 (8)C11—C10—H10119.9
O4—Ni1—O298.06 (7)C13—N4—C17117.1 (2)
N1—O1—H25109 (2)C13—N4—Ni1122.92 (16)
N1—C2—C1123.8 (2)C13—C14—C15118.2 (3)
N1—C2—C3114.5 (2)C13—C14—H14120.9
N2—C3—C2113.5 (2)C14—C13—H13118.2
N2—C3—C4124.9 (2)C14—C15—H15120.6
N3—N2—Ni1118.89 (14)C15—C14—H14120.9
N3—C5—C6115.65 (19)C15—C16—C17119.6 (3)
N4—C13—C14123.5 (2)C15—C16—H16120.2
N4—C13—H13118.2C16—C15—C14118.9 (3)
N4—C17—C16122.6 (3)C16—C15—H15120.6
N4—C17—H17118.7C16—C17—H17118.7
N5—C18—C19123.7 (3)C17—N4—Ni1119.77 (17)
N5—C18—H18118.2C17—C16—H16120.2
N5—C22—C21123.4 (2)C18—N5—Ni1120.63 (18)
N5—C22—H22118.3C18—N5—C22116.2 (2)
O1—N1—Ni1128.27 (16)C18—C19—H19120.7
O2—C5—N3125.85 (19)C19—C18—H18118.2
O2—C5—C6118.48 (19)C19—C20—H20120.7
O3—C9—C8114.7 (2)C20—C19—C18118.6 (3)
O3—C12—H12A109.5C20—C19—H19120.7
O3—C12—H12B109.5C20—C21—C22119.6 (3)
O3—C12—H12C109.5C20—C21—H21120.2
O4—C23—C24116.8 (3)C21—C20—C19118.5 (3)
O5—C23—O4125.5 (2)C21—C20—H20120.7
O5—C23—C24117.7 (2)C21—C22—H22118.3
C2—N1—Ni1115.42 (16)C22—N5—Ni1123.20 (17)
C2—N1—O1116.24 (19)C22—C21—H21120.2
C2—C1—H1A109.5C23—O4—Ni1126.71 (17)
C2—C1—H1B109.5C23—C24—H24A109.5
C2—C1—H1C109.5C23—C24—H24B109.5
C2—C3—C4121.6 (2)C23—C24—H24C109.5
C3—N2—Ni1119.93 (16)H1A—C1—H1B109.5
C3—N2—N3121.13 (19)H1A—C1—H1C109.5
C3—C2—C1121.6 (2)H1B—C1—H1C109.5
C3—C4—H4A109.5H4A—C4—H4B109.5
C3—C4—H4B109.5H4A—C4—H4C109.5
C3—C4—H4C109.5H4B—C4—H4C109.5
C5—N3—N2107.71 (18)H12A—C12—H12B109.5
C5—O2—Ni1110.30 (13)H12A—C12—H12C109.5
C6—C7—H7119.6H12B—C12—H12C109.5
C6—C11—H11119.6H24A—C24—H24B109.5
C7—C6—C11118.2 (2)H24A—C24—H24C109.5
C7—C6—C5119.8 (2)H24B—C24—H24C109.5
N2—Ni1—O2—C55.62 (15)O1—N1—C2—C10.4 (4)
O4—Ni1—O2—C5175.90 (15)Ni1—N1—C2—C2176.86 (19)
N1—Ni1—O2—C55.3 (2)Ni1—N2—C3—C20.6 (3)
N4—Ni1—O2—C595.16 (16)N3—N2—C3—C41.1 (4)
N5—Ni1—O2—C587.23 (15)Ni1—N2—C3—C4178.6 (2)
O2—Ni1—O4—C23166.2 (2)N1—C2—C3—N22.6 (3)
N1—Ni1—O4—C2314.4 (2)C1—C2—C3—N2178.7 (2)
N4—Ni1—O4—C23101.1 (2)N1—C2—C3—C4175.5 (2)
N5—Ni1—O4—C2376.0 (2)C1—C2—C3—C43.3 (4)
N2—Ni1—N1—C23.57 (17)Ni1—O2—C5—N36.9 (3)
O4—Ni1—N1—C2174.86 (16)Ni1—O2—C5—C6171.69 (16)
O2—Ni1—N1—C23.8 (3)N2—N3—C5—O23.3 (3)
N4—Ni1—N1—C287.29 (18)N2—N3—C5—C6175.32 (18)
N5—Ni1—N1—C296.29 (18)O2—C5—C6—C721.6 (3)
N2—Ni1—N1—O1179.4 (2)N3—C5—C6—C7157.1 (2)
O4—Ni1—N1—O12.1 (2)O2—C5—C6—C11159.0 (2)
O2—Ni1—N1—O1179.17 (16)N3—C5—C6—C1122.2 (3)
N4—Ni1—N1—O189.70 (19)C11—C6—C7—C80.9 (4)
N5—Ni1—N1—O186.72 (19)C5—C6—C7—C8178.5 (2)
O2—Ni1—N2—C3177.99 (19)C6—C7—C8—C92.0 (4)
N1—Ni1—N2—C32.14 (17)C12—O3—C9—C104.7 (4)
N4—Ni1—N2—C385.07 (18)C12—O3—C9—C8174.7 (3)
N5—Ni1—N2—C392.33 (18)C7—C8—C9—C101.3 (4)
O2—Ni1—N2—N34.52 (15)C7—C8—C9—O3178.3 (2)
N1—Ni1—N2—N3175.36 (17)O3—C9—C10—C11180.0 (3)
N4—Ni1—N2—N397.43 (16)C8—C9—C10—C110.5 (4)
N5—Ni1—N2—N385.16 (16)C9—C10—C11—C61.6 (4)
C3—N2—N3—C5180.0 (2)C7—C6—C11—C100.8 (4)
Ni1—N2—N3—C52.5 (2)C5—C6—C11—C10179.8 (2)
N2—Ni1—N4—C1351.35 (19)C17—N4—C13—C140.3 (3)
O4—Ni1—N4—C13123.46 (19)Ni1—N4—C13—C14175.48 (19)
O2—Ni1—N4—C1325.45 (18)N4—C13—C14—C151.1 (4)
N1—Ni1—N4—C13127.81 (19)C13—C14—C15—C160.9 (4)
N2—Ni1—N4—C17123.72 (18)C14—C15—C16—C170.0 (4)
O4—Ni1—N4—C1761.47 (18)C13—N4—C17—C160.7 (3)
O2—Ni1—N4—C17159.48 (17)Ni1—N4—C17—C16174.70 (19)
N1—Ni1—N4—C1747.26 (18)C15—C16—C17—N40.8 (4)
N2—Ni1—N5—C1889.76 (19)C22—N5—C18—C190.5 (4)
O4—Ni1—N5—C1885.11 (19)Ni1—N5—C18—C19179.8 (2)
O2—Ni1—N5—C1812.95 (18)N5—C18—C19—C202.0 (4)
N1—Ni1—N5—C18166.27 (19)C18—C19—C20—C212.5 (4)
N2—Ni1—N5—C2290.0 (2)C19—C20—C21—C221.7 (4)
O4—Ni1—N5—C2295.1 (2)C18—N5—C22—C210.5 (4)
O2—Ni1—N5—C22166.8 (2)Ni1—N5—C22—C21179.3 (2)
N1—Ni1—N5—C2213.5 (2)C20—C21—C22—N50.1 (5)
O1—N1—C2—C3178.32 (19)Ni1—O4—C23—O56.0 (4)
Ni1—N1—C2—C34.3 (3)Ni1—O4—C23—C24173.90 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H25···O50.85 (3)1.73 (3)2.552 (3)163 (3)
 

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