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The tridentate Schiff base ligand 2,4-dihydroxy­acetophenone salicylhydrazide, derived from the condensation of 2,4-dihydroxy­acetophenone and salicylhydrazide, in the presence of pyridine and N,N′-dimethyl­formamide, forms a dinuclear distorted square-pyramidal Zn complex with Zn(OAc)2·2H2O, viz. [Zn2(C15H12N2O4)2(C5H5N)2]·2C3H7NO. The complex is centrosymmetric and the two Zn atoms are bridged by two phenolate O atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805021677/wn6369sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805021677/wn6369Isup2.hkl
Contains datablock I

CCDC reference: 274128

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.052
  • wR factor = 0.140
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C23
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 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: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2001); program(s) used to refine structure: SHELXL97 (Sheldrick, 2001); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Bis(µ-2,4-dihydroxyacetophenone salicylhydrazidato)bis[pyridinezinc(II)] dimethylformamide disolvate top
Crystal data top
[Zn2(C15H12N2O4)2(C5H5N)2]·2C3H7NOF(000) = 1040
Mr = 1003.66Dx = 1.445 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 2274 reflections
a = 9.8061 (7) Åθ = 2.2–21.6°
b = 9.9171 (7) ŵ = 1.11 mm1
c = 23.7427 (17) ÅT = 292 K
β = 92.545 (2)°Block, yellow
V = 2306.7 (3) Å30.30 × 0.20 × 0.20 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
4511 independent reflections
Radiation source: fine-focus sealed tube3444 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
φ and ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1112
Tmin = 0.733, Tmax = 0.809k = 1112
12351 measured reflectionsl = 2927
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0678P)2]
where P = (Fo2 + 2Fc2)/3
4511 reflections(Δ/σ)max = 0.001
303 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.34 e Å3
Special details top

Experimental. bis[(2,4-dihydroxyacetophenone-salicylhydrazide)- pyridine-zinc(II)] 2DMF

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
Zn10.06743 (4)0.88969 (4)0.039701 (16)0.03520 (16)
O30.1179 (2)0.9550 (2)0.01047 (10)0.0406 (6)
N10.2270 (3)0.8858 (3)0.14535 (12)0.0429 (8)
N30.1184 (3)0.7255 (3)0.00788 (13)0.0419 (7)
N20.2282 (3)0.9518 (3)0.09301 (12)0.0372 (7)
O10.0249 (3)0.7907 (3)0.11089 (10)0.0471 (7)
C200.3412 (4)0.8977 (3)0.03130 (15)0.0380 (8)
C150.2424 (4)0.9003 (3)0.01476 (16)0.0361 (8)
C70.1192 (4)0.8061 (4)0.14883 (14)0.0370 (8)
C60.1095 (4)0.7275 (4)0.20178 (14)0.0401 (9)
C160.2741 (4)0.8432 (4)0.06595 (16)0.0419 (9)
H160.21070.84880.09620.050*
C170.3970 (4)0.7783 (4)0.07354 (17)0.0475 (10)
C50.0069 (5)0.6505 (4)0.20942 (16)0.0482 (10)
H50.07700.65100.18170.058*
C100.1585 (5)0.6104 (4)0.01614 (19)0.0556 (11)
H100.15800.60340.05520.067*
C130.1564 (7)0.6259 (5)0.0964 (2)0.0858 (18)
H130.15580.63470.13550.103*
C190.4618 (4)0.8291 (4)0.02125 (18)0.0541 (11)
H190.52710.82290.05080.065*
C180.4910 (4)0.7702 (4)0.02899 (19)0.0569 (11)
H180.57330.72530.03290.068*
C40.0206 (5)0.5729 (4)0.25748 (18)0.0626 (13)
H40.09940.52290.26240.075*
C10.2143 (4)0.7265 (4)0.24383 (17)0.0533 (11)
C30.0846 (6)0.5714 (5)0.29771 (19)0.0663 (14)
H30.07700.51860.32980.080*
C140.1166 (5)0.7315 (5)0.06370 (18)0.0719 (15)
H140.08720.81070.08140.086*
C120.1964 (6)0.5090 (5)0.0717 (2)0.0803 (16)
H120.22060.43550.09340.096*
C20.2005 (5)0.6462 (5)0.29148 (18)0.0688 (14)
H20.27040.64340.31920.083*
C110.2009 (6)0.5007 (5)0.0144 (2)0.0795 (16)
H110.23190.42280.00390.095*
O40.4171 (3)0.7257 (3)0.12510 (12)0.0623 (8)
H4A0.47310.66440.12220.093*
O20.3294 (3)0.7995 (4)0.23968 (13)0.0837 (11)
H2A0.32110.85030.21250.126*
N40.3102 (4)0.3881 (4)0.19118 (16)0.0611 (10)
O50.3788 (3)0.5475 (4)0.13010 (14)0.0782 (10)
C80.3255 (4)1.0361 (4)0.08563 (15)0.0389 (9)
C90.4293 (4)1.0649 (4)0.13301 (17)0.0571 (11)
H9A0.38791.05310.16850.086*
H9B0.46131.15600.13000.086*
H9C0.50491.00390.13060.086*
C210.3917 (5)0.4826 (5)0.1746 (2)0.0687 (13)
H210.46660.50320.19850.082*
C220.1914 (6)0.3541 (5)0.1564 (2)0.0804 (15)
H22A0.11370.40210.16940.121*
H22B0.17490.25890.15860.121*
H22C0.20610.37860.11800.121*
C230.3296 (5)0.3222 (5)0.2449 (2)0.0778 (15)
H23A0.41220.35420.26350.117*
H23B0.33580.22650.23930.117*
H23C0.25360.34170.26770.117*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0355 (3)0.0330 (3)0.0369 (3)0.00296 (18)0.00072 (18)0.00277 (17)
O30.0292 (14)0.0416 (14)0.0507 (15)0.0057 (11)0.0014 (12)0.0133 (12)
N10.0385 (19)0.054 (2)0.0358 (16)0.0029 (15)0.0027 (14)0.0033 (14)
N30.0411 (19)0.0360 (18)0.0482 (19)0.0000 (14)0.0048 (15)0.0010 (14)
N20.0382 (18)0.0398 (17)0.0335 (15)0.0015 (14)0.0004 (13)0.0001 (13)
O10.0442 (16)0.0585 (17)0.0382 (14)0.0114 (13)0.0026 (12)0.0116 (12)
C200.037 (2)0.0333 (19)0.044 (2)0.0029 (16)0.0030 (17)0.0038 (16)
C150.033 (2)0.0266 (18)0.049 (2)0.0031 (15)0.0075 (16)0.0000 (16)
C70.037 (2)0.040 (2)0.0337 (18)0.0068 (16)0.0020 (16)0.0012 (15)
C60.040 (2)0.044 (2)0.0364 (19)0.0056 (17)0.0053 (17)0.0007 (16)
C160.038 (2)0.038 (2)0.051 (2)0.0044 (17)0.0030 (18)0.0009 (18)
C170.048 (3)0.042 (2)0.055 (2)0.0053 (18)0.017 (2)0.0043 (19)
C50.060 (3)0.044 (2)0.041 (2)0.001 (2)0.0039 (19)0.0033 (18)
C100.064 (3)0.046 (2)0.057 (3)0.005 (2)0.002 (2)0.004 (2)
C130.138 (6)0.070 (4)0.048 (3)0.034 (3)0.007 (3)0.010 (2)
C190.038 (2)0.059 (3)0.065 (3)0.010 (2)0.003 (2)0.000 (2)
C180.037 (2)0.060 (3)0.074 (3)0.018 (2)0.010 (2)0.008 (2)
C40.081 (4)0.052 (3)0.056 (3)0.001 (2)0.019 (3)0.012 (2)
C10.045 (3)0.068 (3)0.046 (2)0.006 (2)0.0011 (19)0.005 (2)
C30.090 (4)0.066 (3)0.044 (3)0.013 (3)0.014 (3)0.016 (2)
C140.115 (4)0.052 (3)0.047 (3)0.025 (3)0.009 (3)0.004 (2)
C120.107 (5)0.056 (3)0.077 (3)0.027 (3)0.010 (3)0.021 (3)
C20.068 (3)0.094 (4)0.044 (2)0.013 (3)0.009 (2)0.017 (2)
C110.114 (5)0.045 (3)0.079 (4)0.025 (3)0.005 (3)0.002 (2)
O40.063 (2)0.065 (2)0.0598 (18)0.0185 (16)0.0186 (15)0.0102 (15)
O20.061 (2)0.128 (3)0.060 (2)0.020 (2)0.0191 (17)0.025 (2)
N40.061 (3)0.060 (2)0.063 (2)0.008 (2)0.007 (2)0.0087 (19)
O50.072 (2)0.088 (2)0.075 (2)0.0224 (19)0.0095 (19)0.023 (2)
C80.036 (2)0.035 (2)0.045 (2)0.0008 (16)0.0019 (17)0.0068 (16)
C90.050 (3)0.061 (3)0.059 (3)0.010 (2)0.012 (2)0.002 (2)
C210.052 (3)0.078 (4)0.076 (3)0.016 (3)0.003 (3)0.005 (3)
C220.081 (4)0.065 (3)0.094 (4)0.012 (3)0.001 (3)0.006 (3)
C230.073 (4)0.083 (4)0.078 (3)0.003 (3)0.009 (3)0.021 (3)
Geometric parameters (Å, º) top
Zn1—O12.014 (2)C19—C181.370 (5)
Zn1—O3i2.022 (2)C19—H190.9300
Zn1—O32.023 (2)C18—H180.9300
Zn1—N32.056 (3)C4—C31.374 (6)
Zn1—N22.071 (3)C4—H40.9300
Zn1—Zn1i3.1415 (8)C1—O21.348 (5)
O3—C151.344 (4)C1—C21.395 (6)
O3—Zn1i2.022 (2)C3—C21.370 (7)
N1—C71.325 (5)C3—H30.9300
N1—N21.405 (4)C14—H140.9300
N3—C141.326 (5)C12—C111.363 (6)
N3—C101.328 (5)C12—H120.9300
N2—C81.287 (5)C2—H20.9300
O1—C71.272 (4)C11—H110.9300
C20—C191.394 (5)O4—H4A0.8200
C20—C151.429 (5)O2—H2A0.8200
C20—C8i1.462 (5)N4—C211.303 (6)
C15—C161.389 (5)N4—C221.438 (6)
C7—C61.486 (5)N4—C231.439 (6)
C6—C51.392 (5)O5—C211.239 (5)
C6—C11.401 (5)C8—C20i1.462 (5)
C16—C171.385 (5)C8—C91.511 (5)
C16—H160.9300C9—H9A0.9600
C17—O41.353 (4)C9—H9B0.9600
C17—C181.374 (6)C9—H9C0.9600
C5—C41.388 (5)C21—H210.9300
C5—H50.9300C22—H22A0.9600
C10—C111.381 (6)C22—H22B0.9600
C10—H100.9300C22—H22C0.9600
C13—C121.350 (6)C23—H23A0.9600
C13—C141.372 (6)C23—H23B0.9600
C13—H130.9300C23—H23C0.9600
O1—Zn1—O3i158.56 (11)C20—C19—H19117.7
O1—Zn1—O3103.14 (10)C19—C18—C17119.1 (4)
O3i—Zn1—O378.10 (10)C19—C18—H18120.4
O1—Zn1—N398.03 (11)C17—C18—H18120.4
O3i—Zn1—N3101.98 (12)C3—C4—C5118.7 (5)
O3—Zn1—N3107.55 (11)C3—C4—H4120.6
O1—Zn1—N279.19 (11)C5—C4—H4120.6
O3i—Zn1—N286.21 (10)O2—C1—C2118.5 (4)
O3—Zn1—N2139.67 (11)O2—C1—C6122.3 (4)
N3—Zn1—N2111.98 (12)C2—C1—C6119.2 (4)
O1—Zn1—Zn1i138.21 (8)C2—C3—C4121.3 (4)
O3i—Zn1—Zn1i39.07 (7)C2—C3—H3119.4
O3—Zn1—Zn1i39.04 (6)C4—C3—H3119.4
N3—Zn1—Zn1i109.14 (9)N3—C14—C13122.7 (4)
N2—Zn1—Zn1i116.65 (8)N3—C14—H14118.6
C15—O3—Zn1i126.8 (2)C13—C14—H14118.6
C15—O3—Zn1130.5 (2)C13—C12—C11118.8 (4)
Zn1i—O3—Zn1101.90 (10)C13—C12—H12120.6
C7—N1—N2111.7 (3)C11—C12—H12120.6
C14—N3—C10117.3 (4)C3—C2—C1120.5 (4)
C14—N3—Zn1121.4 (3)C3—C2—H2119.8
C10—N3—Zn1121.3 (3)C1—C2—H2119.8
C8—N2—N1117.3 (3)C12—C11—C10118.6 (4)
C8—N2—Zn1131.2 (3)C12—C11—H11120.7
N1—N2—Zn1111.5 (2)C10—C11—H11120.7
C7—O1—Zn1111.4 (2)C17—O4—H4A109.5
C19—C20—C15115.4 (3)C1—O2—H2A109.5
C19—C20—C8i119.6 (3)C21—N4—C22119.2 (4)
C15—C20—C8i125.0 (3)C21—N4—C23122.4 (4)
O3—C15—C16118.1 (3)C22—N4—C23118.3 (4)
O3—C15—C20122.5 (3)N2—C8—C20i121.3 (3)
C16—C15—C20119.5 (3)N2—C8—C9120.1 (3)
O1—C7—N1125.8 (3)C20i—C8—C9118.6 (3)
O1—C7—C6117.6 (3)C8—C9—H9A109.5
N1—C7—C6116.6 (3)C8—C9—H9B109.5
C5—C6—C1118.9 (4)H9A—C9—H9B109.5
C5—C6—C7118.8 (3)C8—C9—H9C109.5
C1—C6—C7122.3 (4)H9A—C9—H9C109.5
C17—C16—C15122.2 (4)H9B—C9—H9C109.5
C17—C16—H16118.9O5—C21—N4126.2 (5)
C15—C16—H16118.9O5—C21—H21116.9
O4—C17—C18123.6 (4)N4—C21—H21116.9
O4—C17—C16117.3 (4)N4—C22—H22A109.5
C18—C17—C16119.0 (4)N4—C22—H22B109.5
C4—C5—C6121.4 (4)H22A—C22—H22B109.5
C4—C5—H5119.3N4—C22—H22C109.5
C6—C5—H5119.3H22A—C22—H22C109.5
N3—C10—C11122.8 (4)H22B—C22—H22C109.5
N3—C10—H10118.6N4—C23—H23A109.5
C11—C10—H10118.6N4—C23—H23B109.5
C12—C13—C14119.6 (5)H23A—C23—H23B109.5
C12—C13—H13120.2N4—C23—H23C109.5
C14—C13—H13120.2H23A—C23—H23C109.5
C18—C19—C20124.7 (4)H23B—C23—H23C109.5
C18—C19—H19117.7
O1—Zn1—O3—C1531.5 (3)C8i—C20—C15—C16174.5 (3)
O3i—Zn1—O3—C15170.4 (4)Zn1—O1—C7—N15.7 (5)
N3—Zn1—O3—C1571.4 (3)Zn1—O1—C7—C6173.8 (2)
N2—Zn1—O3—C15120.2 (3)N2—N1—C7—O11.4 (5)
Zn1i—Zn1—O3—C15170.4 (4)N2—N1—C7—C6178.1 (3)
O1—Zn1—O3—Zn1i158.07 (11)O1—C7—C6—C55.4 (5)
O3i—Zn1—O3—Zn1i0.0N1—C7—C6—C5175.0 (3)
N3—Zn1—O3—Zn1i98.97 (13)O1—C7—C6—C1173.5 (4)
N2—Zn1—O3—Zn1i69.36 (18)N1—C7—C6—C16.1 (5)
O1—Zn1—N3—C14159.9 (3)O3—C15—C16—C17176.6 (3)
O3i—Zn1—N3—C1427.8 (4)C20—C15—C16—C172.7 (6)
O3—Zn1—N3—C1453.3 (4)C15—C16—C17—O4179.7 (3)
N2—Zn1—N3—C14118.5 (3)C15—C16—C17—C180.1 (6)
Zn1i—Zn1—N3—C1412.1 (4)C1—C6—C5—C40.2 (6)
O1—Zn1—N3—C1022.2 (3)C7—C6—C5—C4178.7 (4)
O3i—Zn1—N3—C10150.1 (3)C14—N3—C10—C111.8 (7)
O3—Zn1—N3—C10128.8 (3)Zn1—N3—C10—C11176.2 (4)
N2—Zn1—N3—C1059.3 (3)C15—C20—C19—C182.1 (6)
Zn1i—Zn1—N3—C10170.0 (3)C8i—C20—C19—C18176.1 (4)
C7—N1—N2—C8177.3 (3)C20—C19—C18—C170.4 (7)
C7—N1—N2—Zn13.6 (4)O4—C17—C18—C19178.8 (4)
O1—Zn1—N2—C8176.1 (3)C16—C17—C18—C191.5 (6)
O3i—Zn1—N2—C811.9 (3)C6—C5—C4—C31.0 (7)
O3—Zn1—N2—C878.5 (4)C5—C6—C1—O2179.4 (4)
N3—Zn1—N2—C889.5 (3)C7—C6—C1—O21.8 (6)
Zn1i—Zn1—N2—C837.3 (4)C5—C6—C1—C21.4 (6)
O1—Zn1—N2—N14.9 (2)C7—C6—C1—C2177.5 (4)
O3i—Zn1—N2—N1169.2 (2)C5—C4—C3—C21.0 (7)
O3—Zn1—N2—N1102.6 (2)C10—N3—C14—C131.2 (7)
N3—Zn1—N2—N189.4 (2)Zn1—N3—C14—C13176.7 (4)
Zn1i—Zn1—N2—N1143.81 (19)C12—C13—C14—N31.5 (9)
O3i—Zn1—O1—C753.4 (4)C14—C13—C12—C112.3 (10)
O3—Zn1—O1—C7144.3 (2)C4—C3—C2—C10.2 (8)
N3—Zn1—O1—C7105.5 (3)O2—C1—C2—C3179.4 (5)
N2—Zn1—O1—C75.5 (2)C6—C1—C2—C31.4 (7)
Zn1i—Zn1—O1—C7123.6 (2)C13—C12—C11—C102.8 (9)
Zn1i—O3—C15—C16150.4 (3)N3—C10—C11—C122.6 (8)
Zn1—O3—C15—C1641.3 (5)N1—N2—C8—C20i175.5 (3)
Zn1i—O3—C15—C2030.3 (5)Zn1—N2—C8—C20i3.4 (5)
Zn1—O3—C15—C20138.0 (3)N1—N2—C8—C92.4 (5)
C19—C20—C15—O3175.7 (3)Zn1—N2—C8—C9178.7 (3)
C8i—C20—C15—O36.2 (6)C22—N4—C21—O51.2 (8)
C19—C20—C15—C163.5 (5)C23—N4—C21—O5177.0 (5)
Symmetry code: (i) x, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···O10.932.393.119 (5)135
O4—H4A···O5ii0.821.872.677 (4)166
O2—H2A···N10.821.842.561 (4)146
Symmetry code: (ii) x1, y, z.
 

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