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In the title compound, [Zn(C2H3O2)(C11H12N3O2)(C3H4N2)], the Zn atom is five-coordinate in a ZnN3O2 trigonal-bipyramidal enviroment. Adjacent mol­ecules are linked by an intermolecular hydrogen bond into a chain running along the a axis of the monoclinic cell.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009912/ng6025sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009912/ng6025Isup2.hkl
Contains datablock I

CCDC reference: 239116

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.036
  • wR factor = 0.089
  • Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O4 .. O4 .. 2.80 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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, 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)[N-(diacetyl monooxime)-N'-benzoylhydrazonato-κ3O,N,N'](1H-imidazole-κN3)zinc(II) top
Crystal data top
[Zn(C2H3O2)(C11H12N3O2)(C3H4N2)]F(000) = 848
Mr = 410.75Dx = 1.512 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 11353 reflections
a = 7.731 (2) Åθ = 3.4–27.4°
b = 18.334 (4) ŵ = 1.39 mm1
c = 12.931 (3) ÅT = 293 K
β = 100.07 (3)°Prism, yellow
V = 1804.6 (8) Å30.37 × 0.25 × 0.18 mm
Z = 4
Data collection top
Rigaku RAXIS-RAPID
diffractometer
4122 independent reflections
Radiation source: fine-focus sealed tube3431 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 10 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 1010
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 2323
Tmin = 0.626, Tmax = 0.788l = 1616
16947 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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0509P)2 + 0.4702P]
where P = (Fo2 + 2Fc2)/3
4122 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.47 e Å3
2 restraintsΔρmin = 0.26 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.24758 (3)0.59385 (1)0.26486 (2)0.03707 (9)
N10.3754 (2)0.6577 (1)0.4087 (1)0.0447 (4)
N20.2141 (2)0.7018 (1)0.2298 (1)0.0388 (4)
N30.1204 (2)0.7198 (1)0.1328 (1)0.0415 (4)
N40.4694 (2)0.55362 (9)0.2279 (1)0.0368 (4)
N50.7476 (2)0.5302 (1)0.2388 (2)0.0475 (4)
O10.0921 (2)0.59408 (7)0.1144 (1)0.0453 (4)
O20.4626 (3)0.63416 (9)0.5054 (1)0.0583 (5)
O30.0988 (2)0.52482 (8)0.3268 (1)0.0399 (3)
O40.3254 (2)0.49637 (9)0.4484 (1)0.0599 (5)
C10.4612 (3)0.7792 (1)0.4782 (2)0.0533 (6)
C20.3769 (3)0.7269 (1)0.3964 (2)0.0397 (4)
C30.2841 (3)0.7526 (1)0.2925 (2)0.0398 (4)
C40.2706 (3)0.8320 (1)0.2651 (2)0.0578 (6)
C50.0650 (2)0.6592 (1)0.0810 (2)0.0368 (4)
C60.0403 (3)0.6709 (1)0.0263 (2)0.0378 (4)
C70.0628 (3)0.7407 (1)0.0695 (2)0.0477 (5)
C80.1626 (3)0.7510 (1)0.1677 (2)0.0565 (6)
C90.2430 (3)0.6926 (2)0.2240 (2)0.0568 (6)
C100.2196 (3)0.6231 (2)0.1824 (2)0.0515 (6)
C110.1175 (3)0.6120 (1)0.0849 (2)0.0421 (5)
C120.6186 (3)0.5413 (1)0.2920 (2)0.0438 (5)
C130.6815 (3)0.5350 (2)0.1359 (2)0.0638 (7)
C140.5081 (3)0.5492 (2)0.1291 (2)0.0536 (6)
C150.0732 (3)0.4221 (1)0.4356 (2)0.0509 (5)
C160.1751 (3)0.4851 (1)0.4034 (2)0.0385 (4)
H1A0.43770.76430.54560.080*
H1B0.41440.82720.46210.080*
H1C0.58580.77980.47970.080*
H4A0.26890.83780.19110.087*
H4B0.36990.85740.30360.087*
H4C0.16440.85150.28280.087*
H70.01010.78050.03190.057*
H80.17600.79770.19620.068*
H90.31240.69990.28950.068*
H100.27290.58360.22030.062*
H110.10030.56500.05820.051*
H120.63150.54050.36480.053*
H130.74250.52970.08040.077*
H140.42810.55510.06700.064*
H15A0.10050.37880.39990.076*
H15B0.05020.43210.41750.076*
H15C0.10420.41500.51010.076*
H170.435 (5)0.5896 (7)0.504 (3)0.087*
H180.855 (2)0.527 (1)0.268 (2)0.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0287 (1)0.0398 (1)0.0421 (1)0.00181 (9)0.00455 (9)0.0030 (1)
N10.046 (1)0.046 (1)0.0398 (9)0.0022 (8)0.0006 (7)0.0003 (8)
N20.0334 (8)0.0419 (9)0.0401 (9)0.0047 (7)0.0034 (7)0.0003 (7)
N30.0400 (9)0.0435 (9)0.0388 (9)0.0055 (8)0.0008 (7)0.0016 (7)
N40.0279 (8)0.0430 (9)0.0387 (9)0.0014 (7)0.0036 (6)0.0040 (7)
N50.0269 (8)0.057 (1)0.057 (1)0.0012 (8)0.0035 (8)0.0033 (9)
O10.0437 (8)0.0412 (8)0.0459 (8)0.0010 (6)0.0063 (6)0.0037 (6)
O20.073 (1)0.0521 (9)0.0432 (9)0.0061 (9)0.0075 (8)0.0024 (8)
O30.0278 (6)0.0507 (8)0.0398 (7)0.0003 (6)0.0019 (5)0.0081 (6)
O40.0393 (8)0.060 (1)0.072 (1)0.0087 (7)0.0161 (7)0.0227 (9)
C10.057 (1)0.053 (1)0.047 (1)0.003 (1)0.000 (1)0.010 (1)
C20.0307 (9)0.045 (1)0.043 (1)0.0008 (8)0.0059 (8)0.0057 (9)
C30.032 (1)0.041 (1)0.045 (1)0.0033 (8)0.0053 (8)0.0025 (9)
C40.060 (2)0.043 (1)0.065 (2)0.002 (1)0.005 (1)0.000 (1)
C50.0290 (9)0.044 (1)0.038 (1)0.0025 (8)0.0069 (8)0.0023 (8)
C60.0315 (9)0.047 (1)0.036 (1)0.0050 (8)0.0090 (8)0.0022 (8)
C70.052 (1)0.046 (1)0.045 (1)0.005 (1)0.007 (1)0.001 (1)
C80.063 (2)0.058 (1)0.048 (1)0.012 (1)0.009 (1)0.012 (1)
C90.057 (2)0.076 (2)0.035 (1)0.011 (1)0.002 (1)0.005 (1)
C100.052 (1)0.064 (2)0.038 (1)0.004 (1)0.006 (1)0.009 (1)
C110.042 (1)0.047 (1)0.038 (1)0.0015 (9)0.0091 (8)0.0001 (9)
C120.033 (1)0.056 (1)0.040 (1)0.0032 (9)0.0007 (8)0.000 (1)
C130.045 (1)0.099 (2)0.052 (1)0.010 (1)0.021 (1)0.016 (1)
C140.040 (1)0.082 (2)0.039 (1)0.008 (1)0.0062 (9)0.014 (1)
C150.057 (1)0.051 (1)0.044 (1)0.015 (1)0.007 (1)0.002 (1)
C160.036 (1)0.043 (1)0.035 (1)0.0010 (8)0.0045 (8)0.0010 (8)
Geometric parameters (Å, º) top
Zn1—N12.272 (2)C3—C41.497 (3)
Zn1—N22.037 (2)C4—H4A0.9600
Zn1—N42.000 (2)C4—H4B0.9600
Zn1—O12.100 (2)C4—H4C0.9600
Zn1—O31.972 (1)C5—C61.496 (3)
N1—C21.279 (3)C6—C71.395 (3)
N2—N31.374 (2)C6—C111.392 (3)
N2—C31.290 (3)C7—C81.379 (3)
N3—C51.329 (3)C7—H70.9300
O1—C51.274 (2)C8—C91.380 (4)
O2—N11.382 (2)C8—H80.9300
C2—C31.485 (3)C9—C101.382 (4)
N4—C121.316 (2)C9—H90.9300
N4—C141.365 (3)C10—C111.380 (3)
N5—C121.323 (3)C10—H100.9300
N5—C131.343 (3)C11—H110.9300
N5—H180.85 (3)C12—H120.9300
O2—H170.84 (3)C13—C141.353 (3)
O3—C161.286 (2)C13—H130.9300
O4—C161.223 (2)C14—H140.9300
C1—C21.491 (3)C15—C161.497 (3)
C1—H1A0.9600C15—H15A0.9600
C1—H1B0.9600C15—H15B0.9600
C1—H1C0.9600C15—H15C0.9600
N2—Zn1—N172.65 (7)C5—O1—Zn1110.5 (1)
N2—Zn1—O176.23 (6)C6—C7—H7119.8
N4—Zn1—N196.71 (7)C6—C11—H11119.8
N4—Zn1—N2112.70 (7)C7—C6—C5120.8 (2)
N4—Zn1—O198.95 (7)C7—C8—C9120.5 (2)
O1—Zn1—N1148.61 (6)C7—C8—H8119.8
O3—Zn1—N1101.48 (7)C8—C7—C6120.4 (2)
O3—Zn1—N2130.82 (6)C8—C7—H7119.8
O3—Zn1—N4116.48 (6)C8—C9—C10119.6 (2)
O3—Zn1—O195.60 (6)C8—C9—H9120.2
N1—O2—H17102 (3)C9—C8—H8119.8
N1—C2—C1124.2 (2)C9—C10—H10119.8
N1—C2—C3114.5 (2)C10—C9—H9120.2
N3—N2—Zn1117.5 (1)C10—C11—C6120.3 (2)
N2—C3—C2115.0 (2)C10—C11—H11119.8
N2—C3—C4123.3 (2)C11—C6—C7118.8 (2)
N3—C5—C6115.0 (2)C11—C6—C5120.4 (2)
N4—C12—N5110.9 (2)C11—C10—C9120.4 (2)
N4—C12—H12124.5C11—C10—H10119.8
N4—C14—H14125.5C12—N4—C14105.6 (2)
N5—C12—H12124.5C12—N4—Zn1127.4 (2)
N5—C13—C14106.2 (2)C12—N5—C13108.3 (2)
N5—C13—H13126.9C12—N5—H18124 (2)
O1—C5—N3126.3 (2)C13—N5—H18128 (2)
O1—C5—C6118.7 (2)C13—C14—N4109.1 (2)
O2—N1—Zn1130.8 (1)C13—C14—H14125.5
O3—C16—C15117.3 (2)C14—N4—Zn1125.6 (1)
O4—C16—O3122.7 (2)C14—C13—H13126.9
O4—C16—C15120.0 (2)C16—O3—Zn1117.1 (1)
C2—N1—Zn1114.9 (1)C16—C15—H15A109.5
C2—N1—O2114.1 (2)C16—C15—H15B109.5
C2—C1—H1C109.5C16—C15—H15C109.5
C2—C1—H1A109.5H1A—C1—H1B109.5
C2—C1—H1B109.5H1A—C1—H1C109.5
C2—C3—C4121.7 (2)H1B—C1—H1C109.5
C3—N2—Zn1122.6 (2)H4A—C4—H4B109.5
C3—N2—N3119.8 (2)H4A—C4—H4C109.5
C3—C2—C1121.3 (2)H4B—C4—H4C109.5
C3—C4—H4A109.5H15A—C15—H15B109.5
C3—C4—H4B109.5H15A—C15—H15C109.5
C3—C4—H4C109.5H15B—C15—H15C109.5
C5—N3—N2109.4 (2)
Zn1—N1—C2—C1177.0 (2)N4—Zn1—O3—C1648.8 (2)
Zn1—N1—C2—C33.9 (2)N5—C13—C14—N40.5 (3)
Zn1—N2—N3—C51.6 (2)O1—Zn1—N1—O2172.1 (2)
Zn1—N2—C3—C25.5 (3)O1—Zn1—N1—C212.8 (2)
Zn1—N2—C3—C4175.9 (2)O1—Zn1—N2—N32.0 (1)
Zn1—N4—C12—N5166.1 (2)O1—Zn1—N2—C3178.6 (2)
Zn1—N4—C14—C13166.2 (2)O1—Zn1—N4—C12179.4 (2)
Zn1—O1—C5—N31.9 (3)O1—Zn1—N4—C1415.3 (2)
Zn1—O1—C5—C6178.7 (1)O1—Zn1—O3—C16151.8 (2)
Zn1—O3—C16—O411.6 (3)O1—C5—C6—C7175.3 (2)
Zn1—O3—C16—C15167.2 (2)O1—C5—C6—C114.6 (3)
N1—Zn1—N2—N3177.8 (2)O2—N1—C2—C11.1 (3)
N1—Zn1—N2—C35.6 (2)O2—N1—C2—C3179.8 (2)
N1—Zn1—N4—C1226.7 (2)O3—Zn1—N1—O250.5 (2)
N1—Zn1—N4—C14137.4 (2)O3—Zn1—N1—C2134.4 (2)
N1—Zn1—O1—C59.7 (2)O3—Zn1—N2—N387.5 (2)
N1—Zn1—O3—C1654.7 (2)O3—Zn1—N2—C396.0 (2)
N1—C2—C3—N20.5 (3)O3—Zn1—N4—C1279.7 (2)
N1—C2—C3—C4179.1 (2)O3—Zn1—N4—C14116.2 (2)
N2—Zn1—N1—O2180.0 (2)O3—Zn1—O1—C5132.7 (1)
N2—Zn1—N1—C25.0 (2)C1—C2—C3—N2178.7 (2)
N2—Zn1—N4—C12100.7 (2)C1—C2—C3—C40.1 (3)
N2—Zn1—N4—C1463.4 (2)C3—N2—N3—C5178.3 (2)
N2—Zn1—O1—C52.0 (2)C5—C6—C7—C8178.9 (2)
N2—Zn1—O3—C16131.6 (1)C5—C6—C11—C10177.8 (2)
N2—N3—C5—O10.3 (3)C6—C7—C8—C90.6 (4)
N2—N3—C5—C6179.7 (2)C7—C6—C11—C102.3 (3)
N3—N2—C3—C2178.0 (2)C7—C8—C9—C101.5 (4)
N3—N2—C3—C40.6 (3)C8—C9—C10—C110.4 (4)
N3—C5—C6—C75.3 (3)C9—C10—C11—C61.5 (4)
N3—C5—C6—C11174.8 (2)C11—C6—C7—C81.2 (3)
N4—Zn1—N1—O268.3 (2)C12—N4—C14—C130.7 (3)
N4—Zn1—N1—C2106.8 (2)C12—N5—C13—C140.2 (3)
N4—Zn1—N2—N392.1 (2)C13—N5—C12—N40.2 (3)
N4—Zn1—N2—C384.5 (2)C14—N4—C12—N50.5 (3)
N4—Zn1—O1—C5109.4 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H18···O3i0.85 (3)1.91 (3)2.756 (2)176 (3)
O2—H17···O40.84 (3)1.99 (3)2.789 (2)159 (4)
Symmetry code: (i) x+1, y, z.
 

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