[N-(2-Oxido­phenyl)­salicyl­aldiminato-κ³N,O,O′](2,2′:6′,2′′-ter­pyridine-κ³N)copper(II)

The title compound, [Cu(C₁₃H₉NO₂)(C₁₅H₁₁N₃)], was prepared by direct reaction of the ligands with copper(II) salts in methanol solution. The air-stable compound crystallizes in the mononclinic space group C2/c. Although the imine portion of the chelate is disordered over a twofold axis, the copper environment is well defined as a meridionally substituted, tetragonally distorted octahedron.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.045
• wR factor = 0.105
• Data-to-parameter ratio = 11.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: XSCANS/P4 (Siemens, 1994); cell refinement: XSCANS/P4; data reduction: XSCANS/P4; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

[Cu(C13H9NO2)(C15H11N3)]	F(000) = 1044
Mr = 508.02	Dx = 1.482 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 20 reflections
a = 17.132 (3) Å	θ = 1.5–22.5°
b = 13.918 (3) Å	µ = 0.99 mm^−1
c = 9.793 (2) Å	T = 293 K
β = 102.87 (3)°	Rhomb, dark green
V = 2276.5 (8) Å^3	0.5 × 0.3 × 0.3 mm
Z = 4

Data collection

Siemens P4 diffractometer	1395 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
ω scans	h = −20→1
Absorption correction: ψ scan (XSCANS/P4; Siemens, 1994)	k = −1→16
Tmin = 0.666, Tmax = 0.743	l = −11→11
2417 measured reflections	3 standard reflections every 47 reflections
1997 independent reflections	intensity decay: none

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0421P)^2 + 0.7221P] where P = (Fo^2 + 2Fc^2)/3
1997 reflections	(Δ/σ)max < 0.001
171 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.34 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	Occ. (<1)
Cu1	1.0000	0.21678 (5)	0.2500	0.0441 (2)
O1	1.07961 (17)	0.2199 (2)	0.1352 (3)	0.0660 (8)
N1	1.0194 (3)	0.3559 (4)	0.2259 (6)	0.0321 (14)	0.50
N2	0.90201 (19)	0.1705 (2)	0.0544 (3)	0.0511 (8)
N3	1.0000	0.0664 (3)	0.2500	0.0364 (9)
C1	0.9833 (5)	0.4226 (6)	0.2780 (8)	0.040 (2)	0.50
C2	1.0718 (2)	0.3912 (3)	0.1335 (4)	0.0540 (11)
C3	1.0972 (3)	0.4770 (3)	0.0845 (4)	0.0665 (12)
C4	1.1476 (3)	0.4795 (3)	−0.0064 (4)	0.0610 (11)
C5	1.1735 (2)	0.3934 (3)	−0.0502 (4)	0.0537 (10)
C6	1.1509 (2)	0.3075 (3)	−0.0033 (4)	0.0487 (10)
C7	1.0995 (2)	0.3028 (3)	0.0908 (4)	0.0483 (10)
C8	0.8528 (3)	0.2267 (3)	−0.0395 (4)	0.0654 (11)
C9	0.8014 (3)	0.1907 (4)	−0.1551 (5)	0.0735 (14)
C10	0.8004 (3)	0.0947 (4)	−0.1774 (4)	0.0713 (13)
C11	0.8498 (3)	0.0351 (3)	−0.0835 (4)	0.0613 (11)
C12	0.8997 (2)	0.0764 (3)	0.0335 (3)	0.0424 (9)
C13	0.9529 (2)	0.0178 (2)	0.1433 (3)	0.0400 (8)
C14	0.9540 (2)	−0.0821 (3)	0.1398 (4)	0.0540 (10)
C15	1.0000	−0.1315 (4)	0.2500	0.0597 (16)
H1	1.0000	0.490 (5)	0.2500	0.09 (2)*
H3A	1.0794	0.5347	0.1145	0.080*
H4A	1.1640	0.5377	−0.0376	0.073*
H5A	1.2070	0.3938	−0.1130	0.064*
H6A	1.1698	0.2507	−0.0342	0.058*
H8A	0.8540	0.2928	−0.0248	0.078*
H9A	0.7678	0.2313	−0.2173	0.088*
H10A	0.7662	0.0689	−0.2561	0.086*
H11A	0.8498	−0.0309	−0.0981	0.074*
H14A	0.9239	−0.1150	0.0633	0.065*
H15A	1.0000	−0.1983	0.2500	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0617 (5)	0.0313 (4)	0.0410 (4)	0.000	0.0147 (3)	0.000
O1	0.081 (2)	0.0681 (18)	0.0540 (16)	−0.0311 (17)	0.0270 (15)	−0.0001 (15)
N1	0.032 (4)	0.027 (3)	0.038 (4)	0.005 (3)	0.009 (3)	−0.004 (3)
N2	0.057 (2)	0.0481 (19)	0.0461 (18)	0.0051 (17)	0.0082 (16)	−0.0014 (16)
N3	0.041 (2)	0.033 (2)	0.037 (2)	0.000	0.013 (2)	0.000
C1	0.046 (6)	0.033 (4)	0.038 (6)	0.000 (4)	0.007 (3)	−0.002 (4)
C2	0.036 (2)	0.089 (3)	0.036 (2)	−0.003 (2)	0.0064 (17)	0.003 (2)
C3	0.065 (3)	0.068 (3)	0.065 (3)	0.027 (2)	0.012 (2)	−0.003 (2)
C4	0.068 (3)	0.051 (3)	0.066 (3)	0.005 (2)	0.019 (2)	0.012 (2)
C5	0.057 (2)	0.056 (3)	0.055 (2)	−0.007 (2)	0.025 (2)	0.0011 (19)
C6	0.052 (2)	0.049 (3)	0.049 (2)	−0.0091 (18)	0.0178 (19)	−0.0062 (17)
C7	0.045 (2)	0.065 (3)	0.0341 (19)	−0.0160 (19)	0.0061 (17)	−0.0010 (18)
C8	0.071 (3)	0.065 (3)	0.055 (3)	0.009 (2)	0.005 (2)	0.003 (2)
C9	0.062 (3)	0.099 (4)	0.055 (3)	0.003 (3)	0.005 (2)	0.014 (3)
C10	0.057 (3)	0.106 (4)	0.047 (2)	−0.023 (3)	0.003 (2)	0.001 (3)
C11	0.063 (3)	0.068 (3)	0.053 (2)	−0.026 (2)	0.013 (2)	−0.006 (2)
C12	0.041 (2)	0.050 (2)	0.039 (2)	−0.0088 (18)	0.0153 (17)	−0.0026 (18)
C13	0.048 (2)	0.0360 (19)	0.041 (2)	−0.0067 (17)	0.0203 (18)	−0.0048 (16)
C14	0.068 (3)	0.041 (2)	0.060 (2)	−0.014 (2)	0.030 (2)	−0.0104 (19)
C15	0.076 (4)	0.030 (3)	0.082 (4)	0.000	0.038 (4)	0.000

Geometric parameters (Å, º)

Cu1—O1	1.952 (3)	C5—C6	1.369 (5)
Cu1—N1	1.987 (5)	C5—H5A	0.930
Cu1—N3	2.093 (4)	C6—C7	1.410 (5)
Cu1—N2	2.339 (3)	C6—H6A	0.930
O1—C7	1.305 (4)	C8—C9	1.366 (6)
N1—C1	1.283 (7)	C8—H8A	0.930
N1—C2	1.493 (6)	C9—C10	1.353 (6)
C1—H1	1.04 (6)	C9—H9A	0.930
N2—C12	1.326 (5)	C10—C11	1.380 (6)
N2—C8	1.350 (5)	C10—H10A	0.930
N3—C13	1.351 (4)	C11—C12	1.392 (5)
C2—C3	1.393 (6)	C11—H11A	0.930
C2—C7	1.416 (5)	C12—C13	1.488 (5)
C3—C4	1.372 (5)	C13—C14	1.391 (5)
C3—H3A	0.930	C14—C15	1.371 (5)
C4—C5	1.378 (5)	C14—H14A	0.930
C4—H4A	0.930	C15—H15A	0.930
O1—Cu1—O1^i	177.48 (18)	C2—C3—H3A	118.8
O1—Cu1—N1^i	101.73 (16)	C3—C4—C5	118.2 (4)
O1^i—Cu1—N1^i	75.75 (16)	C3—C4—H4A	120.9
O1—Cu1—N1	75.75 (16)	C5—C4—H4A	120.9
O1^i—Cu1—N1	101.73 (16)	C6—C5—C4	121.3 (4)
O1—Cu1—N3	91.26 (9)	C6—C5—H5A	119.3
O1—Cu1—N2	90.03 (11)	C4—C5—H5A	119.3
N1—Cu1—N2	106.2 (2)	C5—C6—C7	121.7 (3)
N3—Cu1—N2	74.02 (8)	C5—C6—H6A	119.2
O1—Cu1—N2^i	90.67 (11)	C7—C6—H6A	119.2
N1—Cu1—N2^i	104.9 (2)	O1—C7—C6	120.4 (4)
N3—Cu1—N2^i	74.02 (8)	O1—C7—C2	122.7 (4)
N2—Cu1—N2^i	148.03 (16)	C6—C7—C2	116.9 (3)
C7—O1—Cu1	118.6 (3)	N2—C8—C9	122.8 (4)
C1—N1—C2	114.3 (5)	N2—C8—H8A	118.6
C1^i—N1—Cu1	165.9 (7)	C9—C8—H8A	118.6
C1—N1—Cu1	123.4 (4)	C10—C9—C8	118.6 (4)
C2—N1—Cu1	122.1 (3)	C10—C9—H9A	120.7
C1^i—C1—C2^i	162.8 (3)	C8—C9—H9A	120.7
N1^i—C1—C2^i	72.4 (6)	C9—C10—C11	120.2 (4)
N1—C1—C2^i	116.4 (6)	C9—C10—H10A	119.9
C1^i—C1—H1	64.9 (17)	C11—C10—H10A	119.9
N1^i—C1—H1	155.1 (19)	C10—C11—C12	118.3 (4)
N1—C1—H1	111.4 (18)	C10—C11—H11A	120.9
C2^i—C1—H1	132.2 (17)	C12—C11—H11A	120.9
C12—N2—C8	118.3 (4)	N2—C12—C11	121.8 (4)
C12—N2—Cu1	113.0 (2)	N2—C12—C13	115.9 (3)
C8—N2—Cu1	128.6 (3)	C11—C12—C13	122.3 (4)
C13—N3—C13^i	119.9 (4)	N3—C13—C14	120.7 (4)
C13—N3—Cu1	120.1 (2)	N3—C13—C12	116.7 (3)
C13^i—N3—Cu1	120.1 (2)	C14—C13—C12	122.7 (3)
C3—C2—C7	119.5 (3)	C15—C14—C13	119.4 (4)
C3—C2—C1^i	103.7 (4)	C15—C14—H14A	120.3
C7—C2—C1^i	136.8 (4)	C13—C14—H14A	120.3
C3—C2—N1	140.1 (4)	C14^i—C15—C14	119.8 (5)
C7—C2—N1	100.4 (4)	C14^i—C15—H15A	120.1
C4—C3—C2	122.4 (4)	C14—C15—H15A	120.1
C4—C3—H3A	118.8

Symmetry code: (i) −x+2, y, −z+1/2.