(Benzoato-κO,O')(quinoline-2-carboxyl-ato-κN,O)(quinoline-2-carboxylic acid-κN,O)copper(II).

The crystal structure of the title compound, [Cu(C(10)H(6)NO(2))(C(7)H(5)O(2))(C(10)H(7)NO(2))], contains copper(II) ions five-coordinated in a distorted trigonal-bipyramidal environment. The equatorial plane is occupied by three O atoms, one from the carboxyl-ate group of the benzoate ion considered as occupying a single coordination site, the other two from two carboxyl-ate groups of the quinaldic acid and quinaldate ligands. The axial positions are occupied by the N atoms of the quinoline ring system. The metal ion lies on a twofold axis that bisects the benzoate ion. The quinaldate and quinaldic acid ligands are equivalent by symmetry, and the carboxyl-ate/carboxyl groups are disordered. The disordered H atom is shared between the carboxyl-ate groups of adjacent quinaldic acid mol-ecules. Such hydrogen bonds delineate zigzag chains that run along the c axis. The structure is very similar to that of the Mn(II) analog.

Related literature

For related literature, see: Zurowska et al. (2007 ▶); Dobrzynska et al. (2005 ▶); Kumar & Gandotra (1980 ▶); Catterick et al. (1974 ▶); Martins et al. (2008 ▶).

Experimental

Crystal data

[Cu(C10H6NO2)(C7H5O2)(C10H7NO2)]

M = 529.97

Monoclinic,

a = 19.1140 (9) Å

b = 11.4665 (5) Å

c = 12.1885 (8) Å

β = 118.788 (1)°

V = 2341.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.98 mm−1

T = 293 (2) K

0.26 × 0.22 × 0.20 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.75, T max = 0.82

27106 measured reflections

2928 independent reflections

2536 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.104

S = 1.06

2928 reflections

178 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014268/bt2705sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014268/bt2705Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C10H6NO2)(C7H5O2)(C10H7NO2)]	F000 = 1084
Mr = 529.97	Dx = 1.504 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4050 reflections
a = 19.1140 (9) Å	θ = 3.2–26.8º
b = 11.4665 (5) Å	µ = 0.98 mm−1
c = 12.1885 (8) Å	T = 293 (2) K
β = 118.7880 (10)º	Block, green
V = 2341.2 (2) Å3	0.26 × 0.22 × 0.20 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	2928 independent reflections
Radiation source: fine-focus sealed tube	2536 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
T = 293(2) K	θmax = 28.4º
φ and ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)	h = −24→25
Tmin = 0.75, Tmax = 0.82	k = −15→15
27106 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0492P)2 + 2.1952P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2928 reflections	Δρmax = 0.38 e Å−3
178 parameters	Δρmin = −0.32 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.5000	0.31494 (3)	0.2500	0.04408 (13)
O1	0.51571 (18)	0.1520 (3)	0.3083 (3)	0.0467 (7)	0.50
O2	0.47650 (18)	0.1264 (3)	0.1065 (3)	0.0517 (7)	0.50
C1	0.4960 (2)	0.0874 (4)	0.2116 (3)	0.0406 (9)	0.50
O3	0.49011 (9)	0.42154 (18)	0.10765 (18)	0.0766 (6)
H1	0.5218	0.4412	0.0837	0.115*	0.50
O4	0.39680 (14)	0.5024 (3)	−0.0713 (3)	0.1504 (15)
N1	0.37963 (10)	0.34319 (16)	0.15664 (16)	0.0460 (4)
C2	0.5000	−0.0419 (3)	0.2500	0.0568 (8)
C3	0.50955 (16)	−0.1029 (3)	0.3531 (2)	0.0671 (7)
H3	0.5165	−0.0628	0.4239	0.080*
C4	0.50904 (19)	−0.2216 (3)	0.3528 (3)	0.0774 (8)
H4	0.5149	−0.2620	0.4228	0.093*
C5	0.5000	−0.2814 (3)	0.2500	0.0767 (11)
H5	0.5000	−0.3625	0.2500	0.092*
C6	0.41763 (13)	0.4477 (2)	0.0220 (2)	0.0563 (5)
C7	0.35528 (12)	0.40982 (19)	0.05672 (19)	0.0492 (5)
C8	0.27586 (13)	0.4476 (2)	−0.0157 (2)	0.0631 (6)
H8	0.2609	0.4935	−0.0865	0.076*
C9	0.22163 (14)	0.4154 (3)	0.0204 (3)	0.0690 (7)
H9	0.1688	0.4392	−0.0260	0.083*
C10	0.24486 (14)	0.3469 (2)	0.1267 (3)	0.0632 (6)
C11	0.19152 (17)	0.3123 (3)	0.1708 (4)	0.0827 (9)
H11	0.1385	0.3361	0.1280	0.099*
C12	0.21650 (19)	0.2459 (4)	0.2729 (4)	0.0950 (11)
H12	0.1807	0.2246	0.3007	0.114*
C13	0.2958 (2)	0.2080 (3)	0.3386 (3)	0.0862 (9)
H13	0.3122	0.1617	0.4095	0.103*
C14	0.34976 (15)	0.2385 (3)	0.2997 (2)	0.0657 (6)
H14	0.4022	0.2122	0.3431	0.079*
C15	0.32525 (13)	0.30941 (19)	0.1942 (2)	0.0522 (5)

	U11	U22	U33	U12	U13	U23
Cu1	0.03721 (19)	0.03809 (19)	0.0498 (2)	0.000	0.01525 (15)	0.000
O1	0.0443 (16)	0.0374 (16)	0.0491 (16)	−0.0029 (13)	0.0152 (13)	−0.0017 (14)
O2	0.0571 (17)	0.0465 (17)	0.0476 (16)	−0.0006 (13)	0.0221 (14)	0.0053 (13)
C1	0.0313 (17)	0.039 (2)	0.047 (2)	0.0006 (17)	0.015 (2)	−0.0005 (15)
O3	0.0441 (8)	0.0868 (13)	0.0932 (13)	0.0102 (8)	0.0286 (8)	0.0495 (11)
O4	0.0687 (14)	0.217 (4)	0.144 (2)	0.0178 (17)	0.0337 (15)	0.124 (2)
N1	0.0362 (8)	0.0478 (9)	0.0496 (9)	−0.0066 (7)	0.0172 (7)	−0.0082 (7)
C2	0.0363 (13)	0.0389 (15)	0.094 (2)	0.000	0.0301 (15)	0.000
C3	0.0658 (15)	0.0756 (17)	0.0649 (14)	−0.0121 (13)	0.0356 (12)	−0.0229 (13)
C4	0.087 (2)	0.0765 (18)	0.0623 (15)	−0.0115 (15)	0.0309 (14)	0.0163 (14)
C5	0.080 (3)	0.0383 (16)	0.092 (3)	0.000	0.026 (2)	0.000
C6	0.0461 (11)	0.0635 (14)	0.0533 (11)	−0.0014 (10)	0.0192 (9)	0.0046 (10)
C7	0.0401 (10)	0.0490 (11)	0.0510 (11)	−0.0015 (8)	0.0158 (8)	−0.0064 (9)
C8	0.0441 (11)	0.0684 (15)	0.0636 (13)	0.0069 (10)	0.0155 (10)	−0.0013 (12)
C9	0.0395 (11)	0.0742 (17)	0.0812 (17)	0.0045 (11)	0.0194 (11)	−0.0122 (14)
C10	0.0425 (11)	0.0688 (15)	0.0784 (16)	−0.0107 (10)	0.0291 (11)	−0.0234 (13)
C11	0.0506 (14)	0.101 (2)	0.105 (2)	−0.0152 (14)	0.0443 (16)	−0.0185 (19)
C12	0.0675 (18)	0.126 (3)	0.114 (3)	−0.0322 (19)	0.0611 (19)	−0.022 (2)
C13	0.0775 (19)	0.106 (3)	0.088 (2)	−0.0260 (17)	0.0494 (17)	0.0001 (17)
C14	0.0536 (13)	0.0770 (17)	0.0695 (14)	−0.0168 (12)	0.0320 (12)	−0.0058 (13)
C15	0.0416 (10)	0.0560 (13)	0.0595 (12)	−0.0126 (9)	0.0247 (9)	−0.0154 (10)

Cu1—O1i	1.970 (3)	C3—C4	1.361 (4)
Cu1—O1	1.970 (3)	C3—H3	0.9300
Cu1—N1	2.0424 (16)	C4—C5	1.364 (4)
Cu1—N1i	2.0424 (16)	C4—H4	0.9300
Cu1—O3i	2.0553 (16)	C5—C4i	1.364 (4)
Cu1—O3	2.0553 (16)	C5—H5	0.9300
O1—C1i	0.777 (4)	C6—C7	1.508 (3)
O1—O2i	1.018 (4)	C7—C8	1.407 (3)
O1—O1i	1.249 (7)	C8—C9	1.358 (4)
O1—C1	1.285 (4)	C8—H8	0.9300
O2—O1i	1.018 (4)	C9—C10	1.392 (4)
O2—C1	1.233 (5)	C9—H9	0.9300
C1—O1i	0.777 (4)	C10—C15	1.416 (3)
C1—C1i	0.872 (8)	C10—C11	1.419 (4)
C1—C2	1.545 (5)	C11—C12	1.336 (5)
O3—C6	1.306 (3)	C11—H11	0.9300
O3—H1	0.8200	C12—C13	1.400 (5)
O4—C6	1.187 (3)	C12—H12	0.9300
N1—C7	1.318 (3)	C13—C14	1.371 (4)
N1—C15	1.378 (3)	C13—H13	0.9300
C2—C3i	1.372 (3)	C14—C15	1.398 (4)
C2—C3	1.372 (3)	C14—H14	0.9300
C2—C1i	1.545 (5)
O1i—Cu1—O1	36.95 (19)	C3—C2—C1i	104.3 (2)
O1i—Cu1—N1	90.82 (10)	C4—C3—C2	120.7 (2)
O1—Cu1—N1	106.65 (10)	C4—C3—H3	119.6
O1i—Cu1—N1i	106.65 (10)	C2—C3—H3	119.6
O1—Cu1—N1i	90.82 (10)	C3—C4—C5	120.2 (3)
N1—Cu1—N1i	161.74 (10)	C3—C4—H4	119.9
O1i—Cu1—O3i	143.58 (12)	C5—C4—H4	119.9
O1—Cu1—O3i	108.87 (12)	C4i—C5—C4	119.6 (4)
N1—Cu1—O3i	89.83 (7)	C4i—C5—H5	120.2
N1i—Cu1—O3i	79.30 (7)	C4—C5—H5	120.2
O1i—Cu1—O3	108.87 (12)	O4—C6—O3	128.6 (2)
O1—Cu1—O3	143.58 (12)	O4—C6—C7	118.4 (2)
N1—Cu1—O3	79.30 (7)	O3—C6—C7	112.78 (19)
N1i—Cu1—O3	89.83 (7)	N1—C7—C8	123.5 (2)
O3i—Cu1—O3	107.02 (13)	N1—C7—C6	116.81 (18)
C1i—O1—O2i	85.6 (5)	C8—C7—C6	119.6 (2)
O2i—O1—O1i	156.1 (4)	C9—C8—C7	118.3 (2)
O2i—O1—C1	127.1 (3)	C9—C8—H8	120.9
C1i—O1—Cu1	145.0 (5)	C7—C8—H8	120.9
O2i—O1—Cu1	124.3 (3)	C8—C9—C10	120.3 (2)
O1i—O1—Cu1	71.52 (10)	C8—C9—H9	119.9
C1—O1—Cu1	106.8 (3)	C10—C9—H9	119.9
O1i—C1—C1i	102.2 (5)	C9—C10—C15	118.9 (2)
O1i—C1—O2	55.5 (4)	C9—C10—C11	123.0 (3)
C1i—C1—O2	157.5 (4)	C15—C10—C11	118.1 (3)
O1i—C1—O1	69.6 (5)	C12—C11—C10	120.8 (3)
O2—C1—O1	123.6 (4)	C12—C11—H11	119.6
O1i—C1—C2	166.6 (5)	C10—C11—H11	119.6
C1i—C1—C2	73.61 (15)	C11—C12—C13	120.8 (3)
O2—C1—C2	127.5 (4)	C11—C12—H12	119.6
O1—C1—C2	109.0 (3)	C13—C12—H12	119.6
C6—O3—Cu1	116.24 (14)	C14—C13—C12	120.7 (3)
C6—O3—H1	109.5	C14—C13—H13	119.7
Cu1—O3—H1	132.9	C12—C13—H13	119.7
C7—N1—C15	118.85 (18)	C13—C14—C15	119.5 (3)
C7—N1—Cu1	114.11 (14)	C13—C14—H14	120.3
C15—N1—Cu1	126.73 (15)	C15—C14—H14	120.3
C3i—C2—C3	118.6 (3)	N1—C15—C14	119.8 (2)
C3i—C2—C1	104.3 (2)	N1—C15—C10	120.2 (2)
C3—C2—C1	137.1 (2)	C14—C15—C10	120.0 (2)
C3i—C2—C1i	137.1 (2)
O1i—Cu1—O1—C1i	−15.7 (7)	O3i—Cu1—N1—C15	−65.38 (18)
N1—Cu1—O1—C1i	52.4 (9)	O3—Cu1—N1—C15	−172.74 (19)
N1i—Cu1—O1—C1i	−132.9 (8)	O1i—C1—C2—C3i	108 (2)
O3i—Cu1—O1—C1i	148.1 (8)	C1i—C1—C2—C3i	−179.0 (5)
O3—Cu1—O1—C1i	−42.1 (9)	O2—C1—C2—C3i	9.9 (5)
O1i—Cu1—O1—O2i	−159.9 (6)	O1—C1—C2—C3i	−170.9 (3)
N1—Cu1—O1—O2i	−91.8 (4)	O1i—C1—C2—C3	−72 (2)
N1i—Cu1—O1—O2i	82.8 (4)	C1i—C1—C2—C3	1.4 (7)
O3i—Cu1—O1—O2i	3.9 (4)	O2—C1—C2—C3	−169.7 (3)
O3—Cu1—O1—O2i	173.7 (3)	O1—C1—C2—C3	9.5 (4)
N1—Cu1—O1—O1i	68.1 (3)	O1i—C1—C2—C1i	−73 (2)
N1i—Cu1—O1—O1i	−117.2 (3)	O2—C1—C2—C1i	−171.1 (9)
O3i—Cu1—O1—O1i	163.8 (3)	O1—C1—C2—C1i	8.2 (3)
O3—Cu1—O1—O1i	−26.4 (4)	C3i—C2—C3—C4	−0.4 (2)
O1i—Cu1—O1—C1	5.6 (2)	C1—C2—C3—C4	179.1 (3)
N1—Cu1—O1—C1	73.7 (3)	C1i—C2—C3—C4	179.9 (3)
N1i—Cu1—O1—C1	−111.6 (2)	C2—C3—C4—C5	0.9 (4)
O3i—Cu1—O1—C1	169.4 (2)	C3—C4—C5—C4i	−0.4 (2)
O3—Cu1—O1—C1	−20.8 (3)	Cu1—O3—C6—O4	−176.0 (3)
O1i—O2—C1—C1i	6.7 (16)	Cu1—O3—C6—C7	9.5 (3)
O1i—O2—C1—O1	−15.3 (5)	C15—N1—C7—C8	−0.9 (3)
O1i—O2—C1—C2	163.8 (7)	Cu1—N1—C7—C8	−175.00 (18)
C1i—O1—C1—O1i	152.6 (11)	C15—N1—C7—C6	177.99 (18)
O2i—O1—C1—O1i	155.8 (7)	Cu1—N1—C7—C6	3.9 (2)
Cu1—O1—C1—O1i	−9.2 (4)	O4—C6—C7—N1	175.9 (3)
O2i—O1—C1—C1i	3.3 (8)	O3—C6—C7—N1	−9.0 (3)
O1i—O1—C1—C1i	−152.6 (11)	O4—C6—C7—C8	−5.2 (4)
Cu1—O1—C1—C1i	−161.7 (7)	O3—C6—C7—C8	170.0 (2)
C1i—O1—C1—O2	166.0 (10)	N1—C7—C8—C9	1.2 (4)
O2i—O1—C1—O2	169.3 (3)	C6—C7—C8—C9	−177.7 (2)
O1i—O1—C1—O2	13.4 (4)	C7—C8—C9—C10	0.1 (4)
Cu1—O1—C1—O2	4.2 (5)	C8—C9—C10—C15	−1.5 (4)
C1i—O1—C1—C2	−13.3 (5)	C8—C9—C10—C11	178.7 (3)
O2i—O1—C1—C2	−10.0 (5)	C9—C10—C11—C12	179.6 (3)
O1i—O1—C1—C2	−165.9 (6)	C15—C10—C11—C12	−0.2 (4)
Cu1—O1—C1—C2	−175.0 (2)	C10—C11—C12—C13	−0.5 (6)
O1i—Cu1—O3—C6	81.1 (2)	C11—C12—C13—C14	0.1 (6)
O1—Cu1—O3—C6	97.5 (2)	C12—C13—C14—C15	0.9 (5)
N1—Cu1—O3—C6	−6.11 (19)	C7—N1—C15—C14	179.8 (2)
N1i—Cu1—O3—C6	−171.4 (2)	Cu1—N1—C15—C14	−6.9 (3)
O3i—Cu1—O3—C6	−92.6 (2)	C7—N1—C15—C10	−0.6 (3)
O1i—Cu1—N1—C7	−108.25 (18)	Cu1—N1—C15—C10	172.68 (16)
O1—Cu1—N1—C7	−142.16 (17)	C13—C14—C15—N1	178.1 (2)
N1i—Cu1—N1—C7	55.17 (14)	C13—C14—C15—C10	−1.5 (4)
O3i—Cu1—N1—C7	108.16 (16)	C9—C10—C15—N1	1.8 (3)
O3—Cu1—N1—C7	0.80 (15)	C11—C10—C15—N1	−178.4 (2)
O1i—Cu1—N1—C15	78.21 (19)	C9—C10—C15—C14	−178.6 (2)
O1—Cu1—N1—C15	44.3 (2)	C11—C10—C15—C14	1.2 (4)
N1i—Cu1—N1—C15	−118.37 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O4ii	0.82	1.76	2.560 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1⋯O4i	0.82	1.76	2.560 (3)	165

Symmetry code: (i) .