Bis­[2-(quinolin-3-yl­imino­methyl)­phenolato-κ²N,O]copper(II)

In the title complex, [Cu(C₁₆H₁₁N₂O)₂], the Cu^II atom lies on a center of symmetry within a square-planar trans-N₂O₂ coordination geometry and adopts a stepped conformation with regard to the bulky Schiff base ligands.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.039
• wR factor = 0.112
• Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.6497
            Proportion of unique data used    0.6299
            Ratio reflections to parameters   9.9665
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.97
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a

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

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Computing details

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(I)

Crystal data

[Cu(C16H11N2O)2]	F(000) = 574.0
Mr = 558.09	Dx = 1.505 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yab	Cell parameters from 25 reflections
a = 12.767 (3) Å	θ = 10.0–13.3°
b = 7.346 (2) Å	µ = 0.93 mm^−1
c = 13.133 (5) Å	T = 298 K
β = 90.66 (3)°	Plate, brown
V = 1231.6 (6) Å^3	0.40 × 0.30 × 0.20 mm
Z = 2

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.028
ω–2θ scans	θmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = −6→16
Tmin = 0.724, Tmax = 0.831	k = −9→3
3539 measured reflections	l = −17→17
2832 independent reflections	3 standard reflections every 150 reflections
1784 reflections with I > 2σ(I)	intensity decay: 0.2%

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0388P)^2 + 0.6777P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.112	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.30 e Å^−3
1784 reflections	Δρmin = −0.32 e Å^−3
179 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	1.0000	0.0000	1.0000	0.0320 (2)
O1	1.0809 (2)	−0.1032 (3)	0.8944 (2)	0.0345 (5)
N1	0.9096 (2)	−0.2287 (3)	1.0051 (2)	0.0319 (6)
N2	0.6716 (2)	−0.3774 (4)	1.1406 (2)	0.0393 (6)
C1	0.9551 (2)	−0.3191 (4)	0.8324 (2)	0.0337 (7)
C2	0.9194 (3)	−0.4253 (5)	0.7492 (3)	0.0452 (8)
C3	0.9695 (3)	−0.4239 (5)	0.6585 (3)	0.0504 (9)
C4	1.0601 (3)	−0.3201 (5)	0.6485 (3)	0.0483 (9)
C5	1.0983 (3)	−0.2181 (5)	0.7282 (3)	0.0405 (8)
C6	1.0452 (2)	−0.2089 (4)	0.8219 (2)	0.0311 (6)
C7	0.8995 (2)	−0.3324 (4)	0.9258 (2)	0.0377 (7)
C8	0.7373 (2)	−0.3260 (5)	1.0701 (2)	0.0397 (7)
C9	0.8428 (2)	−0.2698 (4)	1.0885 (2)	0.0320 (6)
C10	0.8757 (2)	−0.2527 (4)	1.1874 (2)	0.0352 (7)
C11	0.8062 (2)	−0.2980 (4)	1.2661 (2)	0.0343 (7)
C12	0.8325 (3)	−0.2761 (5)	1.3705 (2)	0.0441 (8)
C13	0.7636 (3)	−0.3277 (6)	1.4442 (3)	0.0507 (9)
C14	0.6672 (3)	−0.4064 (5)	1.4171 (3)	0.0480 (9)
C15	0.6381 (3)	−0.4254 (5)	1.3178 (3)	0.0433 (8)
C16	0.7059 (2)	−0.3679 (4)	1.2397 (2)	0.0342 (7)
H1	0.8592	−0.5001	0.7567	0.0547*
H2	0.9431	−0.4932	0.6029	0.0614*
H3	1.0960	−0.3202	0.5856	0.0583*
H4	1.1618	−0.1527	0.7204	0.0491*
H5	0.8493	−0.4278	0.9305	0.0463*
H6	0.7126	−0.3268	1.0016	0.0481*
H7	0.9445	−0.2108	1.2033	0.0427*
H8	0.8983	−0.2250	1.3895	0.0534*
H9	0.7807	−0.3104	1.5142	0.0616*
H10	0.6213	−0.4475	1.4686	0.0580*
H11	0.5721	−0.4780	1.3004	0.0525*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0260 (2)	0.0329 (3)	0.0371 (3)	−0.0055 (3)	0.0045 (2)	−0.0064 (3)
O1	0.0284 (10)	0.039 (1)	0.036 (1)	−0.0056 (9)	0.0025 (8)	−0.0085 (10)
N1	0.031 (1)	0.031 (1)	0.033 (1)	−0.006 (1)	−0.001 (1)	0.000 (1)
N2	0.032 (1)	0.049 (2)	0.037 (1)	−0.009 (1)	−0.001 (1)	0.000 (1)
C1	0.035 (1)	0.032 (2)	0.034 (2)	−0.001 (1)	−0.001 (1)	−0.005 (1)
C2	0.043 (2)	0.042 (2)	0.051 (2)	−0.006 (2)	0.002 (2)	−0.010 (2)
C3	0.060 (2)	0.050 (2)	0.042 (2)	0.004 (2)	−0.002 (2)	−0.016 (2)
C4	0.062 (2)	0.048 (2)	0.036 (2)	0.007 (2)	0.014 (2)	−0.006 (2)
C5	0.043 (2)	0.037 (2)	0.042 (2)	−0.001 (1)	0.010 (1)	−0.002 (1)
C6	0.030 (1)	0.031 (2)	0.033 (2)	0.006 (1)	0.001 (1)	0.000 (1)
C7	0.035 (2)	0.034 (2)	0.044 (2)	−0.010 (1)	−0.001 (1)	−0.002 (1)
C8	0.035 (2)	0.049 (2)	0.035 (2)	−0.011 (1)	−0.002 (1)	0.002 (2)
C9	0.028 (1)	0.032 (2)	0.036 (2)	−0.005 (1)	0.000 (1)	0.001 (1)
C10	0.032 (2)	0.037 (2)	0.036 (2)	−0.003 (1)	−0.003 (1)	0.001 (1)
C11	0.033 (1)	0.033 (2)	0.036 (2)	0.001 (1)	−0.001 (1)	0.001 (1)
C12	0.045 (2)	0.051 (2)	0.037 (2)	−0.001 (2)	−0.003 (1)	−0.002 (2)
C13	0.062 (2)	0.058 (2)	0.032 (2)	0.007 (2)	0.001 (2)	−0.001 (2)
C14	0.056 (2)	0.049 (2)	0.040 (2)	0.001 (2)	0.016 (2)	0.004 (2)
C15	0.043 (2)	0.041 (2)	0.047 (2)	−0.004 (2)	0.010 (1)	0.003 (2)
C16	0.034 (2)	0.031 (2)	0.038 (2)	0.001 (1)	0.003 (1)	0.001 (1)

Geometric parameters (Å, º)

Cu1—O1	1.898 (2)	C5—C6	1.413 (4)
Cu1—O1^i	1.898 (2)	C5—H4	0.950
Cu1—N1	2.040 (2)	C7—H5	0.950
Cu1—N1^i	2.040 (2)	C8—C9	1.426 (4)
O1—C6	1.306 (4)	C8—H6	0.950
N1—C7	1.296 (4)	C9—C10	1.367 (4)
N1—C9	1.429 (4)	C10—C11	1.409 (4)
N2—C8	1.312 (4)	C10—H7	0.950
N2—C16	1.371 (4)	C11—C12	1.416 (4)
C1—C2	1.414 (5)	C11—C16	1.420 (4)
C1—C6	1.415 (4)	C12—C13	1.369 (5)
C1—C7	1.427 (4)	C12—H8	0.950
C2—C3	1.359 (5)	C13—C14	1.402 (5)
C2—H1	0.950	C13—H9	0.950
C3—C4	1.393 (5)	C14—C15	1.359 (5)
C3—H2	0.950	C14—H10	0.950
C4—C5	1.372 (5)	C15—C16	1.414 (5)
C4—H3	0.950	C15—H11	0.950
O1—Cu1—O1^i	180.0	N1—C7—H5	116.2
O1—Cu1—N1	90.46 (9)	C1—C7—H5	116.7
O1—Cu1—N1^i	89.54 (9)	N2—C8—C9	125.0 (3)
O1^i—Cu1—N1	89.54 (9)	N2—C8—H6	117.2
O1^i—Cu1—N1^i	90.46 (9)	C9—C8—H6	117.7
N1—Cu1—N1^i	180.0	N1—C9—C8	120.2 (3)
Cu1—O1—C6	125.6 (2)	N1—C9—C10	122.0 (3)
Cu1—N1—C7	120.6 (2)	C8—C9—C10	117.8 (3)
Cu1—N1—C9	122.9 (2)	C9—C10—C11	119.1 (3)
C7—N1—C9	115.9 (3)	C9—C10—H7	120.7
C8—N2—C16	117.1 (3)	C11—C10—H7	120.2
C2—C1—C6	119.7 (3)	C10—C11—C12	122.6 (3)
C2—C1—C7	117.9 (3)	C10—C11—C16	118.7 (3)
C6—C1—C7	122.5 (3)	C12—C11—C16	118.7 (3)
C1—C2—C3	121.6 (3)	C11—C12—C13	120.4 (3)
C1—C2—H1	119.5	C11—C12—H8	119.8
C3—C2—H1	118.9	C13—C12—H8	119.7
C2—C3—C4	119.1 (3)	C12—C13—C14	120.2 (3)
C2—C3—H2	120.3	C12—C13—H9	120.3
C4—C3—H2	120.6	C14—C13—H9	119.5
C3—C4—C5	121.0 (3)	C13—C14—C15	121.1 (3)
C3—C4—H3	119.4	C13—C14—H10	119.8
C5—C4—H3	119.6	C15—C14—H10	119.2
C4—C5—C6	121.4 (3)	C14—C15—C16	120.2 (3)
C4—C5—H4	119.4	C14—C15—H11	120.2
C6—C5—H4	119.3	C16—C15—H11	119.7
O1—C6—C1	123.1 (3)	N2—C16—C11	121.9 (3)
O1—C6—C5	119.7 (3)	N2—C16—C15	118.8 (3)
C1—C6—C5	117.2 (3)	C11—C16—C15	119.3 (3)
N1—C7—C1	127.2 (3)
Cu1—O1—C6—C1	−26.3 (4)	C2—C1—C6—C5	−2.9 (4)
Cu1—O1—C6—C5	154.6 (2)	C2—C3—C4—C5	−0.9 (6)
Cu1—N1—C7—C1	7.8 (4)	C3—C2—C1—C6	−0.3 (5)
Cu1—N1—C9—C8	132.8 (3)	C3—C2—C1—C7	−178.4 (3)
Cu1—N1—C9—C10	−45.5 (4)	C3—C4—C5—C6	−2.4 (5)
O1—Cu1—N1—C7	−25.6 (2)	C5—C6—C1—C7	175.1 (3)
O1—Cu1—N1—C9	163.9 (2)	C7—N1—C9—C8	−38.2 (4)
O1—C6—C1—C2	177.9 (3)	C7—N1—C9—C10	143.6 (3)
O1—C6—C1—C7	−4.1 (5)	C8—N2—C16—C11	2.8 (5)
O1—C6—C5—C4	−176.5 (3)	C8—N2—C16—C15	−178.8 (3)
N1—Cu1—O1—C6	35.4 (2)	C8—C9—C10—C11	2.6 (5)
N1—C7—C1—C2	−169.1 (3)	C9—C8—N2—C16	3.2 (5)
N1—C7—C1—C6	12.8 (5)	C9—C10—C11—C12	−177.0 (3)
N1—C9—C8—N2	175.7 (3)	C9—C10—C11—C16	2.8 (5)
N1—C9—C10—C11	−179.1 (3)	C10—C11—C12—C13	−177.8 (3)
N2—C8—C9—C10	−6.0 (5)	C10—C11—C16—C15	175.8 (3)
N2—C16—C11—C10	−5.8 (5)	C11—C12—C13—C14	1.3 (6)
N2—C16—C11—C12	174.0 (3)	C11—C16—C15—C14	2.9 (5)
N2—C16—C15—C14	−175.6 (3)	C12—C11—C16—C15	−4.4 (5)
C1—C2—C3—C4	2.3 (6)	C12—C13—C14—C15	−3.0 (6)
C1—C6—C5—C4	4.2 (5)	C13—C12—C11—C16	2.4 (5)
C1—C7—N1—C9	179.0 (3)	C13—C14—C15—C16	0.9 (6)

Symmetry code: (i) −x+2, −y, −z+2.