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The title complex, [Cu(C14H12N3O2)2], consists of two deprotonated 2-acetyl­pyridine salicylhydrazone ligands coordinated to the copper as N,N,O-tridentate ligands, forming a neutral complex. The Cu atom lies on a twofold rotation axis. The structure is stabilized by intra­molecular O—H...N hydrogen bonding, and π–π stacking inter­actions between the pyridyl and benzene rings lead to a two-dimensional network in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019337/hg2032sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019337/hg2032Isup2.hkl
Contains datablock I

CCDC reference: 613707

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.036
  • wR factor = 0.077
  • Data-to-parameter ratio = 11.0

checkCIF/PLATON results

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Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.21 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 16 N2 -CU1 -N2 -C6 -131.50 0.30 2.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 21 N2 -CU1 -N2 -N3 40.90 0.20 2.555 1.555 1.555 1.555
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 25.50 From the CIF: _reflns_number_total 1968 Count of symmetry unique reflns 1230 Completeness (_total/calc) 160.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 738 Fraction of Friedel pairs measured 0.600 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis{N-(2-hydroxybenzoyl)-N'-[1-(2-pyridyl)ethylidene]hydrazinato]copper(II) top
Crystal data top
[Cu(C14H12N3O2)2]F(000) = 1180
Mr = 572.07Dx = 1.516 Mg m3
Orthorhombic, Aba2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2acCell parameters from 1902 reflections
a = 12.570 (2) Åθ = 2.7–22.0°
b = 18.731 (4) ŵ = 0.92 mm1
c = 10.6482 (19) ÅT = 293 K
V = 2507.1 (8) Å3Block, green
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1628 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Graphite monochromatorθmax = 25.5°, θmin = 2.2°
φ and ω scansh = 1315
6226 measured reflectionsk = 2222
1968 independent reflectionsl = 1012
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)] = 0.036H-atom parameters constrained
wR(F2) = 0.077 w = 1/[σ2(Fo2) + (0.035P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1968 reflectionsΔρmax = 0.52 e Å3
179 parametersΔρmin = 0.16 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.018 (19)
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
Cu10.00000.00000.15509 (8)0.05477 (18)
O10.01374 (17)0.08533 (14)0.0199 (3)0.0647 (7)
O20.2825 (2)0.16322 (19)0.0921 (3)0.0944 (11)
H20.26840.13660.03320.142*
N10.0829 (2)0.05852 (16)0.2994 (3)0.0559 (7)
N20.1460 (2)0.03693 (15)0.1424 (4)0.0536 (7)
N30.1671 (2)0.08738 (15)0.0528 (3)0.0578 (8)
C10.0453 (4)0.1023 (2)0.3847 (5)0.0796 (12)
H10.02660.11380.38240.096*
C20.1079 (5)0.1322 (2)0.4778 (5)0.1006 (17)
H2A0.07860.16190.53860.121*
C30.2147 (5)0.1166 (3)0.4774 (5)0.1028 (18)
H30.25930.13700.53710.123*
C40.2557 (4)0.0708 (2)0.3891 (5)0.0782 (13)
H40.32770.05940.38850.094*
C50.1877 (3)0.0426 (2)0.3020 (3)0.0565 (9)
C60.2216 (3)0.00967 (18)0.2055 (4)0.0575 (10)
C70.3361 (3)0.0287 (2)0.1857 (5)0.0852 (15)
H7A0.36660.00290.12440.128*
H7B0.37400.02400.26360.128*
H7C0.34120.07700.15650.128*
C80.0776 (3)0.10946 (18)0.0042 (3)0.0534 (9)
C90.0921 (3)0.16456 (17)0.1038 (3)0.0537 (9)
C100.0033 (3)0.1935 (2)0.1616 (4)0.0657 (10)
H100.06390.18030.13350.079*
C110.0114 (3)0.2405 (2)0.2577 (4)0.0781 (12)
H110.04960.25960.29410.094*
C120.1099 (3)0.2599 (2)0.3009 (4)0.0823 (13)
H120.11590.29120.36830.099*
C130.1991 (3)0.2334 (2)0.2454 (5)0.0803 (13)
H130.26570.24670.27540.096*
C140.1916 (3)0.1868 (2)0.1446 (4)0.0687 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0486 (3)0.0660 (3)0.0497 (3)0.0084 (3)0.0000.000
O10.0515 (15)0.0773 (18)0.0651 (18)0.0171 (11)0.0059 (12)0.0092 (15)
O20.0515 (18)0.113 (3)0.119 (3)0.0051 (14)0.0164 (19)0.033 (2)
N10.0522 (18)0.0604 (18)0.055 (2)0.0076 (14)0.0031 (14)0.0059 (16)
N20.0467 (15)0.0590 (15)0.0552 (19)0.0014 (12)0.0021 (16)0.0092 (19)
N30.0551 (18)0.0591 (18)0.059 (2)0.0060 (13)0.0037 (15)0.0004 (16)
C10.087 (3)0.074 (3)0.078 (3)0.001 (2)0.016 (3)0.010 (3)
C20.148 (5)0.083 (3)0.070 (4)0.028 (3)0.005 (4)0.013 (3)
C30.142 (5)0.091 (4)0.075 (4)0.055 (3)0.036 (3)0.010 (3)
C40.080 (3)0.078 (3)0.076 (3)0.026 (3)0.030 (3)0.021 (3)
C50.053 (2)0.061 (2)0.056 (2)0.0171 (17)0.0125 (18)0.017 (2)
C60.0448 (19)0.061 (2)0.067 (3)0.0001 (16)0.0022 (16)0.0221 (19)
C70.050 (2)0.095 (3)0.111 (5)0.0083 (18)0.005 (2)0.028 (3)
C80.056 (2)0.054 (2)0.050 (2)0.0076 (18)0.0088 (18)0.0109 (18)
C90.051 (2)0.055 (2)0.055 (3)0.0110 (15)0.0062 (18)0.0050 (19)
C100.054 (2)0.073 (2)0.070 (3)0.0091 (19)0.0036 (19)0.010 (2)
C110.071 (3)0.081 (3)0.082 (3)0.010 (2)0.002 (2)0.013 (3)
C120.085 (3)0.085 (3)0.077 (4)0.016 (2)0.010 (2)0.014 (2)
C130.065 (3)0.087 (3)0.090 (3)0.011 (2)0.029 (2)0.017 (3)
C140.054 (2)0.079 (3)0.073 (3)0.002 (2)0.008 (2)0.001 (2)
Geometric parameters (Å, º) top
Cu1—N21.966 (3)C3—H30.9300
Cu1—N2i1.966 (3)C4—C51.368 (5)
Cu1—N1i2.156 (3)C4—H40.9300
Cu1—N12.156 (3)C5—C61.482 (5)
Cu1—O1i2.158 (3)C6—C71.498 (5)
Cu1—O12.158 (3)C7—H7A0.9600
O1—C81.260 (4)C7—H7B0.9600
O2—C141.346 (4)C7—H7C0.9600
O2—H20.8200C8—C91.491 (5)
N1—C11.311 (5)C9—C101.386 (5)
N1—C51.351 (4)C9—C141.388 (5)
N2—C61.272 (4)C10—C111.354 (6)
N2—N31.369 (4)C10—H100.9300
N3—C81.344 (4)C11—C121.371 (5)
C1—C21.384 (6)C11—H110.9300
C1—H10.9300C12—C131.361 (6)
C2—C31.375 (7)C12—H120.9300
C2—H2A0.9300C13—C141.387 (6)
C3—C41.372 (7)C13—H130.9300
N2—Cu1—N2i172.1 (2)C3—C4—H4120.9
N2—Cu1—N1i108.75 (13)N1—C5—C4122.5 (4)
N2i—Cu1—N1i77.11 (13)N1—C5—C6114.4 (3)
N2—Cu1—N177.11 (13)C4—C5—C6123.1 (4)
N2i—Cu1—N1108.75 (13)N2—C6—C5114.6 (3)
N1i—Cu1—N189.07 (16)N2—C6—C7123.3 (4)
N2—Cu1—O1i98.04 (11)C5—C6—C7122.1 (4)
N2i—Cu1—O1i76.59 (12)C6—C7—H7A109.5
N1i—Cu1—O1i152.95 (10)C6—C7—H7B109.5
N1—Cu1—O1i93.46 (10)H7A—C7—H7B109.5
N2—Cu1—O176.59 (12)C6—C7—H7C109.5
N2i—Cu1—O198.04 (11)H7A—C7—H7C109.5
N1i—Cu1—O193.46 (11)H7B—C7—H7C109.5
N1—Cu1—O1152.95 (10)O1—C8—N3124.1 (3)
O1i—Cu1—O196.32 (15)O1—C8—C9120.3 (3)
C8—O1—Cu1109.2 (2)N3—C8—C9115.6 (3)
C14—O2—H2109.5C10—C9—C14118.0 (4)
C1—N1—C5118.4 (4)C10—C9—C8119.2 (3)
C1—N1—Cu1129.6 (3)C14—C9—C8122.7 (3)
C5—N1—Cu1111.9 (2)C11—C10—C9122.0 (4)
C6—N2—N3120.0 (3)C11—C10—H10119.0
C6—N2—Cu1121.3 (3)C9—C10—H10119.0
N3—N2—Cu1118.2 (2)C10—C11—C12119.6 (4)
C8—N3—N2111.4 (3)C10—C11—H11120.2
N1—C1—C2123.0 (5)C12—C11—H11120.2
N1—C1—H1118.5C13—C12—C11120.1 (4)
C2—C1—H1118.5C13—C12—H12119.9
C3—C2—C1117.8 (5)C11—C12—H12119.9
C3—C2—H2A121.1C12—C13—C14120.7 (4)
C1—C2—H2A121.1C12—C13—H13119.7
C4—C3—C2120.1 (4)C14—C13—H13119.7
C4—C3—H3119.9O2—C14—C13118.1 (4)
C2—C3—H3119.9O2—C14—C9122.5 (4)
C5—C4—C3118.1 (5)C13—C14—C9119.5 (4)
C5—C4—H4120.9
N2—Cu1—O1—C85.5 (2)Cu1—N1—C5—C4177.2 (3)
N2i—Cu1—O1—C8168.6 (2)C1—N1—C5—C6177.5 (3)
N1i—Cu1—O1—C8114.0 (2)Cu1—N1—C5—C60.9 (3)
N1—Cu1—O1—C819.3 (4)C3—C4—C5—N10.6 (6)
O1i—Cu1—O1—C891.3 (2)C3—C4—C5—C6177.3 (4)
N2—Cu1—N1—C1173.4 (4)N3—N2—C6—C5178.2 (3)
N2i—Cu1—N1—C112.1 (4)Cu1—N2—C6—C59.4 (4)
N1i—Cu1—N1—C163.9 (3)N3—N2—C6—C71.4 (5)
O1i—Cu1—N1—C189.2 (3)Cu1—N2—C6—C7170.9 (3)
O1—Cu1—N1—C1159.7 (3)N1—C5—C6—N26.3 (4)
N2—Cu1—N1—C52.7 (2)C4—C5—C6—N2171.7 (3)
N2i—Cu1—N1—C5171.7 (2)N1—C5—C6—C7174.1 (3)
N1i—Cu1—N1—C5112.2 (3)C4—C5—C6—C77.9 (5)
O1i—Cu1—N1—C594.7 (2)Cu1—O1—C8—N33.8 (4)
O1—Cu1—N1—C516.4 (4)Cu1—O1—C8—C9174.4 (2)
N2i—Cu1—N2—C6131.5 (3)N2—N3—C8—O11.6 (4)
N1i—Cu1—N2—C691.5 (3)N2—N3—C8—C9179.9 (3)
N1—Cu1—N2—C67.0 (3)O1—C8—C9—C105.8 (5)
O1i—Cu1—N2—C684.8 (3)N3—C8—C9—C10175.9 (3)
O1—Cu1—N2—C6179.4 (3)O1—C8—C9—C14172.1 (3)
N2i—Cu1—N2—N340.9 (2)N3—C8—C9—C146.2 (5)
N1i—Cu1—N2—N396.0 (2)C14—C9—C10—C112.0 (6)
N1—Cu1—N2—N3179.4 (3)C8—C9—C10—C11176.0 (4)
O1i—Cu1—N2—N387.7 (2)C9—C10—C11—C120.7 (7)
O1—Cu1—N2—N36.9 (2)C10—C11—C12—C131.6 (7)
C6—N2—N3—C8179.7 (3)C11—C12—C13—C140.2 (7)
Cu1—N2—N3—C87.1 (3)C12—C13—C14—O2178.9 (4)
C5—N1—C1—C20.8 (6)C12—C13—C14—C92.9 (6)
Cu1—N1—C1—C2175.1 (3)C10—C9—C14—O2178.1 (4)
N1—C1—C2—C32.1 (7)C8—C9—C14—O24.0 (6)
C1—C2—C3—C42.0 (7)C10—C9—C14—C133.8 (6)
C2—C3—C4—C50.8 (7)C8—C9—C14—C13174.1 (4)
C1—N1—C5—C40.6 (5)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N30.821.822.550 (4)148
 

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