[1-Acetyl­acetone (2-hydroxy­benzoyl)hydrazonato]pyridine­copper(II)

In the title complex, [Cu(C₁₂H₁₂N₂O₃)(C₅H₅N)], the Cu^II atom has a square-planar coordination geometry, formed by the tridentate hydrazone and the monodentate pyridine ligands. The distance of 3.706 (4) Å between the centroids of the nearly parallel [dihedral angle 4.9 (5)°] pyridine ring and the benzene ring of a neighbouring complex mol­ecule suggests the existence of π–π stacking.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.067
• wR factor = 0.220
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.125
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         13
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C8
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C12

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

[Cu(C12H12N2O3)(C5H5N)]	F(000) = 1544
Mr = 374.88	Dx = 1.498 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1882 reflections
a = 12.503 (5) Å	θ = 3.0–19.7°
b = 9.894 (4) Å	µ = 1.33 mm^−1
c = 26.88 (1) Å	T = 298 K
V = 3325 (2) Å^3	Rectangular, green
Z = 8	0.42 × 0.29 × 0.23 mm

Data collection

Siemens SMART CCD area-detector diffractometer	2931 independent reflections
Radiation source: fine-focus sealed tube	1494 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.125
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
Tmin = 0.604, Tmax = 0.749	k = −11→11
15733 measured reflections	l = −32→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.220	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0595P)^2 + 10.1233P] where P = (Fo^2 + 2Fc^2)/3
2931 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.70 e Å^−3
2 restraints	Δρmin = −0.66 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.81627 (7)	0.19885 (10)	0.59883 (3)	0.0501 (4)
N1	0.6669 (5)	0.2299 (7)	0.5917 (2)	0.0504 (16)
N2	0.6038 (5)	0.1441 (7)	0.6205 (2)	0.0505 (16)
N3	0.9699 (5)	0.1639 (7)	0.6146 (2)	0.0529 (17)
O1	0.7676 (4)	0.0617 (5)	0.64429 (18)	0.0524 (13)
O2	0.4348 (4)	0.0500 (6)	0.6606 (2)	0.0749 (18)
H2	0.4712	0.0974	0.6421	0.112*
O3	0.8521 (4)	0.3283 (6)	0.5494 (2)	0.0620 (16)
C1	0.6646 (6)	0.0608 (7)	0.6464 (3)	0.0455 (18)
C2	0.6096 (6)	−0.0340 (8)	0.6801 (3)	0.0466 (19)
C3	0.4992 (7)	−0.0342 (9)	0.6864 (3)	0.058 (2)
C4	0.4519 (7)	−0.1223 (11)	0.7198 (4)	0.076 (3)
H4	0.3782	−0.1200	0.7244	0.092*
C5	0.5111 (9)	−0.2111 (12)	0.7456 (4)	0.084 (3)
H5	0.4781	−0.2693	0.7681	0.101*
C6	0.6225 (9)	−0.2167 (9)	0.7390 (3)	0.071 (3)
H6	0.6633	−0.2800	0.7561	0.085*
C7	0.6701 (6)	−0.1276 (9)	0.7068 (3)	0.060 (2)
H7	0.7439	−0.1296	0.7028	0.072*
C8	0.4971 (6)	0.3208 (9)	0.5594 (4)	0.075 (3)
H8A	0.4672	0.2554	0.5818	0.112*
H8B	0.4746	0.3011	0.5261	0.112*
H8C	0.4731	0.4095	0.5686	0.112*
C9	0.6178 (6)	0.3152 (8)	0.5623 (3)	0.056 (2)
C10	0.6782 (7)	0.4048 (8)	0.5318 (3)	0.059 (2)
H10	0.6399	0.4687	0.5137	0.071*
C11	0.7854 (7)	0.4062 (9)	0.5264 (3)	0.058 (2)
C12	0.8347 (7)	0.5052 (9)	0.4901 (3)	0.070 (3)
H12A	0.9110	0.4947	0.4901	0.106*
H12B	0.8167	0.5958	0.4998	0.106*
H12C	0.8075	0.4879	0.4573	0.106*
C13	0.9969 (7)	0.0739 (9)	0.6492 (3)	0.066 (2)
H13	0.9427	0.0274	0.6657	0.079*
C14	1.1013 (8)	0.0467 (11)	0.6616 (4)	0.088 (3)
H14	1.1166	−0.0185	0.6855	0.106*
C15	1.1821 (7)	0.1148 (11)	0.6391 (4)	0.080 (3)
H15	1.2533	0.0997	0.6475	0.095*
C16	1.1539 (7)	0.2058 (12)	0.6037 (4)	0.083 (3)
H16	1.2069	0.2526	0.5866	0.100*
C17	1.0490 (6)	0.2301 (10)	0.5928 (3)	0.068 (3)
H17	1.0326	0.2955	0.5692	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0397 (6)	0.0661 (7)	0.0444 (6)	0.0035 (5)	−0.0009 (4)	0.0038 (5)
N1	0.051 (4)	0.056 (4)	0.045 (4)	0.003 (3)	−0.002 (3)	0.001 (3)
N2	0.042 (4)	0.058 (4)	0.052 (4)	0.006 (3)	−0.004 (3)	0.002 (3)
N3	0.043 (4)	0.069 (5)	0.046 (4)	−0.003 (3)	0.008 (3)	0.002 (3)
O1	0.038 (3)	0.071 (4)	0.048 (3)	0.001 (3)	−0.003 (2)	0.005 (3)
O2	0.039 (3)	0.092 (5)	0.093 (5)	0.001 (3)	0.002 (3)	0.016 (4)
O3	0.048 (3)	0.073 (4)	0.065 (4)	0.007 (3)	0.001 (3)	0.016 (3)
C1	0.044 (5)	0.054 (5)	0.038 (4)	−0.005 (4)	−0.003 (3)	−0.006 (4)
C2	0.044 (5)	0.051 (5)	0.045 (4)	0.001 (4)	−0.001 (3)	−0.011 (4)
C3	0.055 (6)	0.059 (6)	0.060 (5)	−0.006 (4)	0.002 (4)	−0.007 (4)
C4	0.053 (6)	0.095 (8)	0.080 (7)	−0.015 (5)	0.011 (5)	0.000 (6)
C5	0.078 (8)	0.104 (9)	0.070 (7)	−0.022 (7)	0.009 (5)	0.007 (6)
C6	0.101 (8)	0.059 (6)	0.054 (5)	−0.005 (5)	−0.004 (5)	0.010 (5)
C7	0.051 (5)	0.070 (6)	0.059 (5)	−0.013 (5)	−0.005 (4)	−0.007 (5)
C8	0.050 (5)	0.072 (6)	0.101 (8)	0.010 (5)	−0.022 (5)	0.012 (6)
C9	0.054 (5)	0.060 (5)	0.056 (5)	0.000 (4)	−0.017 (4)	−0.012 (5)
C10	0.068 (6)	0.062 (5)	0.047 (5)	0.005 (5)	−0.012 (4)	0.008 (4)
C11	0.064 (6)	0.066 (6)	0.045 (5)	0.004 (5)	0.000 (4)	−0.001 (4)
C12	0.088 (7)	0.062 (6)	0.061 (6)	−0.005 (5)	0.000 (5)	0.014 (5)
C13	0.054 (5)	0.088 (7)	0.056 (5)	0.004 (5)	0.004 (4)	0.013 (5)
C14	0.052 (6)	0.125 (9)	0.087 (7)	0.013 (6)	−0.010 (5)	0.030 (7)
C15	0.040 (5)	0.131 (9)	0.068 (6)	0.012 (6)	−0.004 (5)	0.007 (6)
C16	0.044 (5)	0.128 (9)	0.076 (7)	0.003 (5)	0.005 (4)	0.027 (7)
C17	0.043 (5)	0.094 (7)	0.067 (6)	−0.002 (5)	0.002 (4)	0.016 (5)

Geometric parameters (Å, º)

Cu1—O1	1.925 (5)	C6—H6	0.9300
Cu1—O3	1.900 (6)	C7—H7	0.9300
Cu1—N1	1.902 (6)	C8—C9	1.512 (9)
Cu1—N3	1.998 (6)	C8—H8A	0.9600
N1—N2	1.394 (9)	C8—H8B	0.9600
N1—C9	1.310 (10)	C8—H8C	0.9600
N2—C1	1.320 (9)	C9—C10	1.424 (11)
N3—C17	1.324 (10)	C10—C11	1.348 (11)
N3—C13	1.330 (10)	C10—H10	0.9300
O1—C1	1.289 (8)	C11—C12	1.515 (10)
O2—C3	1.350 (10)	C12—H12A	0.9600
O2—H2	0.8200	C12—H12B	0.9600
O3—C11	1.292 (9)	C12—H12C	0.9600
C1—C2	1.473 (10)	C13—C14	1.374 (11)
C2—C3	1.391 (10)	C13—H13	0.9300
C2—C7	1.395 (11)	C14—C15	1.357 (13)
C3—C4	1.384 (12)	C14—H14	0.9300
C4—C5	1.343 (13)	C15—C16	1.356 (12)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.405 (13)	C16—C17	1.365 (11)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.371 (11)	C17—H17	0.9300
O3—Cu1—N1	93.0 (3)	C9—C8—H8A	109.5
O3—Cu1—O1	173.8 (2)	C9—C8—H8B	109.5
N1—Cu1—O1	82.4 (2)	H8A—C8—H8B	109.5
O3—Cu1—N3	92.2 (2)	C9—C8—H8C	109.5
N1—Cu1—N3	173.4 (3)	H8A—C8—H8C	109.5
O1—Cu1—N3	92.7 (2)	H8B—C8—H8C	109.5
C9—N1—N2	117.6 (6)	N1—C9—C10	120.0 (7)
C9—N1—Cu1	128.7 (6)	N1—C9—C8	121.5 (8)
N2—N1—Cu1	113.7 (5)	C10—C9—C8	118.5 (8)
C1—N2—N1	110.3 (6)	C11—C10—C9	126.5 (8)
C17—N3—C13	116.9 (8)	C11—C10—H10	116.8
C17—N3—Cu1	122.6 (6)	C9—C10—H10	116.8
C13—N3—Cu1	120.5 (5)	O3—C11—C10	125.8 (8)
C1—O1—Cu1	110.4 (4)	O3—C11—C12	115.5 (8)
C3—O2—H2	109.5	C10—C11—C12	118.6 (8)
C11—O3—Cu1	125.7 (5)	C11—C12—H12A	109.5
O1—C1—N2	123.2 (7)	C11—C12—H12B	109.5
O1—C1—C2	119.9 (7)	H12A—C12—H12B	109.5
N2—C1—C2	116.9 (7)	C11—C12—H12C	109.5
C3—C2—C7	118.3 (8)	H12A—C12—H12C	109.5
C3—C2—C1	122.6 (7)	H12B—C12—H12C	109.5
C7—C2—C1	119.1 (7)	N3—C13—C14	122.8 (8)
O2—C3—C4	117.9 (8)	N3—C13—H13	118.6
O2—C3—C2	121.9 (8)	C14—C13—H13	118.6
C4—C3—C2	120.3 (9)	C15—C14—C13	120.2 (9)
C5—C4—C3	120.8 (9)	C15—C14—H14	119.9
C5—C4—H4	119.6	C13—C14—H14	119.9
C3—C4—H4	119.6	C16—C15—C14	116.6 (9)
C4—C5—C6	120.4 (9)	C16—C15—H15	121.7
C4—C5—H5	119.8	C14—C15—H15	121.7
C6—C5—H5	119.8	C15—C16—C17	121.2 (9)
C7—C6—C5	119.0 (9)	C15—C16—H16	119.4
C7—C6—H6	120.5	C17—C16—H16	119.4
C5—C6—H6	120.5	N3—C17—C16	122.4 (9)
C6—C7—C2	121.1 (8)	N3—C17—H17	118.8
C6—C7—H7	119.4	C16—C17—H17	118.8
C2—C7—H7	119.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.82	2.547 (8)	148
C15—H15···O2^i	0.93	2.35	3.275 (11)	174

Symmetry code: (i) x+1, y, z.