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In the title complex, [Ni(C11H12N3O2)(C2H3O2)(C5H5N)2], the NiII atom exhibits a distorted octahedral geometry, with two N atoms and one O atom of a tridentate butane-2,3-dione monooxime benzoyl­hydrazone ligand and one acetate O atom in the equatorial plane, and two pyridine N atoms in the axial sites. The uncoordinated acetate O atom forms an intramolecular hydrogen bond with the oxime O atom of the hydrazone ligand, with an O...O distance and an O—H...O angle of 2.541 (4) Å and 176 (5)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804022767/cv6375sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804022767/cv6375Isup2.hkl
Contains datablock I

CCDC reference: 252778

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.038
  • wR factor = 0.087
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N1 - C2 .. 8.41 su
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C9 .. 5.33 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C13 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C15 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C20 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for N4 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C23
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 4892 Count of symmetry unique reflns 2765 Completeness (_total/calc) 176.93% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2127 Fraction of Friedel pairs measured 0.769 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 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 1 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)[butane-2,3-dione monooxime benzoylhydrazonato-κ3O,N2,O']bis(pyridine-κN)nickel(II) top
Crystal data top
[Ni(C11H12N3O2)(C2H3O2)(C5H5N)2]F(000) = 1032
Mr = 494.17Dx = 1.364 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 10153 reflections
a = 12.378 (1) Åθ = 3.1–27.5°
b = 14.770 (1) ŵ = 0.84 mm1
c = 13.3291 (7) ÅT = 293 K
β = 99.073 (4)°Prism, green
V = 2406.4 (3) Å30.38 × 0.25 × 0.18 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4892 independent reflections
Radiation source: fine-focus sealed tube4039 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 10 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scanh = 1416
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1919
Tmin = 0.739, Tmax = 0.863l = 1717
11139 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0482P)2 + 0.1684P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
4892 reflectionsΔρmax = 0.31 e Å3
304 parametersΔρmin = 0.20 e Å3
3 restraintsAbsolute structure: Friedel pairs were 2313.
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (1)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.62258 (3)0.18061 (2)0.48281 (3)0.0600 (1)
N10.5839 (2)0.0438 (2)0.4523 (2)0.0716 (7)
N20.5550 (3)0.1803 (2)0.3378 (3)0.0605 (7)
N30.5559 (2)0.2596 (2)0.2831 (2)0.0643 (6)
N40.4661 (2)0.2048 (2)0.5312 (2)0.0654 (6)
N50.7831 (2)0.1655 (2)0.4464 (2)0.0644 (7)
O10.6336 (2)0.3174 (1)0.4412 (2)0.0658 (5)
O20.6055 (2)0.0292 (2)0.5168 (2)0.0871 (7)
O30.6904 (2)0.1899 (2)0.6306 (2)0.0745 (8)
O40.7069 (3)0.0449 (2)0.6764 (2)0.1043 (8)
C10.4915 (4)0.0656 (2)0.3296 (3)0.095 (1)
C20.5306 (3)0.0269 (2)0.3627 (2)0.0683 (7)
C30.5141 (3)0.1066 (2)0.2961 (2)0.0652 (8)
C40.4571 (3)0.1011 (3)0.1890 (2)0.087 (1)
C50.6018 (2)0.3241 (2)0.3449 (2)0.0610 (7)
C60.6176 (3)0.4124 (2)0.2952 (2)0.0634 (7)
C70.5670 (3)0.4308 (2)0.1956 (3)0.079 (1)
C80.5880 (4)0.5109 (3)0.1493 (3)0.091 (1)
C90.6577 (4)0.5739 (3)0.2006 (4)0.097 (1)
C100.7073 (4)0.5570 (3)0.2978 (4)0.094 (1)
C110.6871 (3)0.4773 (2)0.3466 (3)0.0754 (9)
C120.4335 (3)0.2880 (3)0.5449 (4)0.097 (1)
C130.3403 (4)0.3088 (3)0.5856 (4)0.113 (2)
C140.2774 (3)0.2398 (3)0.6119 (3)0.096 (1)
C150.3080 (4)0.1552 (4)0.5951 (4)0.113 (2)
C160.4025 (3)0.1393 (3)0.5551 (3)0.099 (1)
C170.8585 (3)0.2223 (3)0.4894 (3)0.0782 (8)
C180.9647 (3)0.2231 (3)0.4710 (3)0.090 (1)
C190.9938 (4)0.1645 (3)0.4051 (4)0.108 (1)
C200.9175 (4)0.1054 (3)0.3565 (4)0.117 (2)
C210.8116 (3)0.1067 (3)0.3794 (3)0.0855 (9)
C220.7795 (4)0.1580 (3)0.7968 (3)0.104 (1)
C230.7206 (3)0.1276 (3)0.6926 (3)0.0759 (9)
H1A0.48110.10070.38790.143*
H1B0.54480.09460.29540.143*
H1C0.42340.06100.28410.143*
H4A0.42060.15730.17030.131*
H4B0.40430.05290.18300.131*
H4C0.50960.08930.14480.131*
H70.51920.38880.16070.094*
H80.55480.52240.08300.109*
H90.67110.62800.16910.116*
H100.75510.59950.33170.113*
H110.71980.46710.41330.091*
H120.47540.33560.52620.117*
H130.32100.36870.59470.135*
H140.21510.25130.64080.115*
H150.26540.10680.61050.136*
H160.42210.07970.54440.118*
H170.83870.26440.53500.094*
H181.01510.26410.50430.107*
H191.06540.16340.39190.129*
H200.93630.06480.30870.140*
H210.76000.06600.34750.103*
H22A0.81770.10750.83120.155*
H22B0.72690.18050.83640.155*
H22C0.83080.20500.78820.155*
H240.643 (4)0.005 (3)0.570 (2)0.131*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0604 (2)0.0583 (2)0.0646 (2)0.0071 (2)0.0202 (1)0.0065 (2)
N10.075 (2)0.058 (1)0.089 (2)0.007 (1)0.033 (1)0.015 (1)
N20.059 (2)0.058 (2)0.068 (2)0.003 (1)0.020 (1)0.003 (1)
N30.066 (2)0.064 (1)0.067 (1)0.010 (1)0.021 (1)0.008 (1)
N40.055 (2)0.074 (2)0.070 (2)0.006 (1)0.017 (1)0.005 (1)
N50.064 (2)0.062 (1)0.070 (2)0.008 (1)0.022 (1)0.003 (1)
O10.073 (1)0.061 (1)0.067 (1)0.0068 (9)0.022 (1)0.0046 (8)
O20.101 (2)0.065 (1)0.099 (2)0.006 (1)0.028 (1)0.023 (1)
O30.071 (2)0.086 (2)0.069 (2)0.013 (1)0.019 (1)0.0089 (1)
O40.123 (2)0.089 (2)0.094 (2)0.003 (2)0.003 (2)0.028 (1)
C10.104 (3)0.072 (2)0.112 (3)0.013 (2)0.026 (2)0.004 (2)
C20.069 (2)0.067 (2)0.074 (2)0.003 (1)0.027 (2)0.001 (1)
C30.058 (2)0.070 (2)0.073 (2)0.001 (1)0.026 (1)0.002 (2)
C40.091 (3)0.096 (2)0.075 (2)0.004 (2)0.013 (2)0.004 (2)
C50.058 (2)0.063 (2)0.067 (2)0.015 (1)0.024 (1)0.009 (1)
C60.064 (2)0.061 (2)0.071 (2)0.011 (1)0.028 (1)0.007 (1)
C70.088 (2)0.067 (2)0.086 (2)0.018 (2)0.030 (2)0.011 (2)
C80.107 (3)0.083 (2)0.086 (2)0.018 (2)0.028 (2)0.025 (2)
C90.102 (3)0.075 (2)0.123 (4)0.020 (2)0.051 (3)0.039 (2)
C100.085 (3)0.072 (2)0.133 (3)0.006 (2)0.042 (2)0.011 (2)
C110.066 (2)0.071 (2)0.093 (2)0.006 (2)0.028 (2)0.011 (2)
C120.078 (3)0.089 (2)0.135 (3)0.007 (2)0.046 (2)0.026 (2)
C130.089 (3)0.104 (3)0.156 (4)0.010 (2)0.053 (3)0.033 (3)
C140.067 (2)0.139 (4)0.085 (2)0.014 (2)0.027 (2)0.002 (2)
C150.088 (3)0.114 (3)0.153 (5)0.006 (3)0.064 (3)0.028 (3)
C160.090 (3)0.086 (2)0.132 (3)0.015 (2)0.055 (3)0.026 (2)
C170.069 (2)0.089 (2)0.079 (2)0.004 (2)0.018 (2)0.007 (2)
C180.057 (2)0.107 (3)0.106 (2)0.002 (2)0.016 (2)0.004 (2)
C190.066 (3)0.131 (4)0.133 (4)0.005 (2)0.038 (2)0.013 (3)
C200.105 (3)0.120 (4)0.140 (4)0.016 (3)0.062 (3)0.034 (3)
C210.081 (2)0.080 (2)0.103 (2)0.008 (2)0.035 (2)0.013 (2)
C220.097 (3)0.120 (3)0.087 (2)0.021 (2)0.005 (2)0.028 (2)
C230.065 (2)0.088 (2)0.077 (2)0.004 (2)0.018 (2)0.019 (2)
Geometric parameters (Å, º) top
Ni1—N12.102 (2)C7—C81.378 (5)
Ni1—N21.982 (3)C7—H70.9300
Ni1—N52.130 (3)C8—C91.375 (7)
Ni1—N42.165 (3)C8—H80.9300
Ni1—O12.106 (2)C9—C101.367 (6)
Ni1—O32.020 (3)C9—H90.9300
N2—N31.380 (3)C10—C111.387 (5)
C2—C31.469 (4)C10—H100.9300
N1—C21.294 (4)C11—H110.9300
N2—C31.288 (4)C12—C131.384 (5)
N3—C51.328 (4)C12—H120.9300
O1—C51.286 (4)C13—C141.361 (6)
N4—C121.315 (5)C13—H130.9300
N4—C161.319 (5)C14—C151.335 (7)
N5—C171.317 (5)C14—H140.9300
N5—C211.332 (4)C15—C161.381 (5)
O2—N11.378 (3)C15—H150.9300
O2—H240.86 (4)C16—H160.9300
O3—C231.254 (4)C17—C181.374 (5)
O4—C231.246 (5)C17—H170.9300
C1—C21.493 (5)C18—C191.323 (6)
C1—H1A0.9600C18—H180.9300
C1—H1B0.9600C19—C201.373 (7)
C1—H1C0.9600C19—H190.9300
C3—C41.492 (5)C20—C211.392 (6)
C4—H4A0.9600C20—H200.9300
C4—H4B0.9600C21—H210.9300
C4—H4C0.9600C22—C231.531 (6)
C5—C61.489 (4)C22—H22A0.9600
C6—C71.402 (5)C22—H22B0.9600
C6—C111.393 (5)C22—H22C0.9600
N1—Ni1—N491.7 (1)C8—C7—H7119.9
N1—Ni1—N592.7 (1)C8—C9—H9120.0
N1—Ni1—O1153.4 (1)C9—C8—C7120.4 (4)
N2—Ni1—N176.2 (1)C9—C8—H8119.8
N2—Ni1—N491.8 (1)C9—C10—C11120.8 (4)
N2—Ni1—N592.5 (1)C9—C10—H10119.6
N2—Ni1—O177.28 (9)C10—C9—C8120.0 (3)
N2—Ni1—O3176.21 (9)C10—C9—H9120.0
N5—Ni1—N4174.5 (1)C10—C11—C6119.7 (4)
O1—Ni1—N491.04 (9)C10—C11—H11120.1
O1—Ni1—N586.51 (9)C11—C6—C5119.8 (3)
O3—Ni1—N1107.5 (1)C11—C6—C7118.8 (3)
O3—Ni1—N487.2 (1)C11—C10—H10119.6
O3—Ni1—N588.3 (1)C12—N4—Ni1120.3 (2)
O3—Ni1—O199.06 (9)C12—N4—C16116.4 (3)
N1—O2—H24103 (4)C12—C13—H13120.6
N1—C2—C1122.9 (3)C13—C12—H12118.2
N1—C2—C3113.9 (3)C13—C14—H14121.0
N2—C3—C2114.1 (3)C14—C13—C12118.8 (4)
N2—C3—C4123.6 (3)C14—C13—H13120.6
N3—N2—Ni1118.4 (2)C14—C15—C16120.3 (5)
N3—C5—C6115.3 (3)C14—C15—H15119.9
N4—C12—C13123.7 (4)C15—C14—C13117.9 (4)
N4—C12—H12118.2C15—C14—H14121.0
N4—C16—C15122.9 (4)C15—C16—H16118.6
N4—C16—H16118.6C16—N4—Ni1123.2 (3)
N5—C17—C18124.1 (3)C16—C15—H15119.9
N5—C17—H17118.0C17—N5—Ni1117.2 (2)
N5—C21—C20120.9 (4)C17—N5—C21117.5 (3)
N5—C21—H21119.5C17—C18—H18120.6
O1—C5—N3126.7 (2)C18—C17—H17118.0
O1—C5—C6118.0 (3)C18—C19—C20119.4 (4)
O2—N1—Ni1127.9 (2)C18—C19—H19120.3
O3—C23—C22115.6 (4)C19—C18—C17118.7 (4)
O4—C23—O3125.9 (4)C19—C18—H18120.6
O4—C23—C22118.4 (3)C19—C20—C21119.3 (4)
C2—N1—Ni1115.5 (2)C19—C20—H20120.4
C2—N1—O2116.5 (3)C20—C19—H19120.3
C2—C1—H1A109.5C20—C21—H21119.5
C2—C1—H1B109.5C21—N5—Ni1125.2 (3)
C2—C1—H1C109.5C21—C20—H20120.4
C2—C3—C4122.2 (3)C23—O3—Ni1128.9 (3)
C3—N2—Ni1119.9 (2)C23—C22—H22A109.5
C3—N2—N3121.6 (3)C23—C22—H22B109.5
C3—C2—C1123.2 (3)C23—C22—H22C109.5
C3—C4—H4A109.5H1A—C1—H1B109.5
C3—C4—H4B109.5H1A—C1—H1C109.5
C3—C4—H4C109.5H1B—C1—H1C109.5
C5—N3—N2108.7 (2)H4A—C4—H4B109.5
C5—O1—Ni1108.3 (2)H4A—C4—H4C109.5
C6—C7—H7119.9H4B—C4—H4C109.5
C6—C11—H11120.1H22A—C22—H22B109.5
C7—C6—C5121.3 (3)H22A—C22—H22C109.5
C7—C8—H8119.8H22B—C22—H22C109.5
C8—C7—C6120.2 (4)
Ni1—N1—C2—C1176.9 (3)N5—Ni1—N2—C397.2 (3)
Ni1—N1—C2—C34.3 (3)N5—Ni1—O1—C586.9 (2)
Ni1—N2—N3—C52.2 (3)N5—Ni1—O3—C2382.6 (3)
Ni1—N2—C3—C24.3 (4)N5—C17—C18—C191.0 (6)
Ni1—N2—C3—C4177.0 (2)O1—Ni1—N1—O2172.9 (2)
Ni1—N4—C12—C13173.1 (4)O1—Ni1—N1—C29.2 (3)
Ni1—N4—C16—C15173.6 (4)O1—Ni1—N2—N34.9 (2)
Ni1—N5—C17—C18177.8 (3)O1—Ni1—N2—C3176.9 (3)
Ni1—N5—C21—C20176.3 (3)O1—Ni1—N4—C1214.7 (3)
Ni1—O1—C5—N38.4 (3)O1—Ni1—N4—C16170.0 (3)
Ni1—O1—C5—C6171.3 (2)O1—Ni1—N5—C1752.6 (3)
Ni1—O3—C23—O45.8 (6)O1—Ni1—N5—C21123.4 (3)
Ni1—O3—C23—C22174.2 (3)O1—Ni1—O3—C23168.8 (3)
N1—Ni1—N2—N3173.2 (3)O1—C5—C6—C7167.6 (3)
N1—Ni1—N2—C35.0 (2)O1—C5—C6—C1114.9 (4)
N1—Ni1—N4—C12168.2 (3)O2—N1—C2—C11.3 (4)
N1—Ni1—N4—C1616.5 (3)O2—N1—C2—C3177.6 (2)
N1—Ni1—N5—C17154.1 (3)O3—Ni1—N1—C2174.1 (2)
N1—Ni1—N5—C2130.0 (3)O3—Ni1—N1—O23.8 (3)
N1—Ni1—O1—C52.2 (3)O3—Ni1—N4—C1284.4 (3)
N1—Ni1—O3—C239.7 (4)O3—Ni1—N4—C1690.9 (3)
N1—C2—C3—N20.2 (4)O3—Ni1—N5—C1746.6 (3)
N1—C2—C3—C4178.4 (3)O3—Ni1—N5—C21137.4 (3)
N2—Ni1—N1—O2177.1 (3)O3—Ni1—O1—C5174.6 (2)
N2—Ni1—N1—C25.0 (2)C1—C2—C3—N2179.1 (3)
N2—Ni1—N4—C1292.0 (3)C1—C2—C3—C40.4 (5)
N2—Ni1—N4—C1692.7 (3)C3—N2—N3—C5179.6 (3)
N2—Ni1—N5—C17129.7 (3)C5—C6—C7—C8176.2 (3)
N2—Ni1—N5—C2146.3 (3)C5—C6—C11—C10175.8 (3)
N2—Ni1—O1—C56.42 (18)C6—C7—C8—C90.6 (6)
N2—N3—C5—O14.7 (4)C7—C6—C11—C101.8 (5)
N2—N3—C5—C6175.0 (2)C7—C8—C9—C100.4 (6)
N3—N2—C3—C2173.8 (3)C8—C9—C10—C110.9 (6)
N3—N2—C3—C44.8 (5)C9—C10—C11—C61.6 (6)
N3—C5—C6—C712.6 (4)C11—C6—C7—C81.3 (5)
N3—C5—C6—C11164.9 (3)C12—N4—C16—C151.9 (7)
N4—Ni1—N1—C286.5 (2)C12—C13—C14—C151.4 (7)
N4—Ni1—N1—O291.5 (2)C13—C14—C15—C161.9 (7)
N4—Ni1—N2—N395.5 (2)C14—C15—C16—N40.3 (8)
N4—Ni1—N2—C386.3 (3)C16—N4—C12—C132.5 (7)
N4—Ni1—O1—C598.0 (2)C17—N5—C21—C200.4 (6)
N4—Ni1—O3—C23100.6 (3)C17—C18—C19—C200.6 (8)
N4—C12—C13—C140.9 (8)C18—C19—C20—C211.7 (8)
N5—Ni1—N1—O285.2 (2)C19—C20—C21—N51.2 (7)
N5—Ni1—N1—C296.9 (2)C21—N5—C17—C181.5 (5)
N5—Ni1—N2—N381.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H24···O40.86 (4)1.68 (3)2.541 (4)176 (5)
 

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