Tetra-kis(μ-2-anilinobenzoato)bis-[methano-lcopper(II)](Cu-Cu).

The title compound, [Cu(2)(C(13)H(10)NO(2))(4)(CH(4)O)(2)], has been prepared by the reaction of 2-anilinobenzoic acid, HL, with copper(II) nitrate in methanol. This dinuclear complex is arranged around an inversion center. Each Cu atom displays a distorted trigonal-pyramidal coordination with four O atoms from the four ligands L and one axial O atom of the methanol solvent mol-ecule. Each carboxyl-ate group of the ligands L links two Cu atoms, building a dinuclear complex with a Cu-Cu distance of 2.5774 (10) Å. There are intra-molecular N-H⋯O hydrogen bonds, and the H atom of the methanol mol-ecule is involved in weak bifurcated hydrogen-bonding inter-actions with two carboxyl-ate O atoms of related mol-ecules, forming a chain developing parallel to the a axis.

Related literature

For general background, see: Melnik et al. (1998 ▶); Facchin et al. (1998 ▶); Martin & Greenwood (1997 ▶); Moulton et al. (2003 ▶). For a related structure, see: Churchill et al. (1985 ▶).

Experimental

Crystal data

[Cu2(C13H10NO2)4(CH4O)2]

M = 1040.06

Monoclinic,

a = 7.2467 (14) Å

b = 14.171 (3) Å

c = 23.813 (5) Å

β = 97.11 (3)°

V = 2426.6 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.94 mm−1

T = 293 (2) K

0.22 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

23688 measured reflections

5568 independent reflections

3886 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.115

S = 1.05

5568 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038063/dn2398sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038063/dn2398Isup2.hkl

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

[Cu2(C13H10NO2)4(CH4O)2]	F000 = 1076
Mr = 1040.06	Dx = 1.423 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19383 reflections
a = 7.2467 (14) Å	θ = 3.0–27.6º
b = 14.171 (3) Å	µ = 0.94 mm−1
c = 23.813 (5) Å	T = 293 (2) K
β = 97.11 (3)º	Block, black
V = 2426.6 (9) Å3	0.22 × 0.20 × 0.15 mm
Z = 2

Bruker SMART CCD diffractometer	3886 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.073
Monochromator: graphite	θmax = 27.5º
T = 293(2) K	θmin = 3.0º
ω scans	h = −9→9
Absorption correction: none	k = −18→17
23688 measured reflections	l = −30→30
5568 independent reflections

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)] = 0.059	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0338P)2 + 2.4261P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
5568 reflections	Δρmax = 0.41 e Å−3
316 parameters	Δρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Cu1	1.13786 (5)	0.05253 (3)	0.990416 (16)	0.02737 (12)
N1	0.9279 (4)	0.2080 (2)	0.83101 (12)	0.0481 (8)
H1	0.9928	0.1944	0.8612	0.058*
N2	1.0262 (4)	0.3315 (2)	1.06884 (14)	0.0492 (8)
H2	1.0768	0.2917	1.0500	0.059*
O1	0.7459 (3)	0.00204 (19)	0.93852 (11)	0.0549 (7)
O2	0.9804 (3)	0.09287 (18)	0.92135 (9)	0.0424 (6)
O3	1.0252 (3)	0.15225 (16)	1.03190 (10)	0.0436 (6)
O4	0.7885 (3)	0.06096 (16)	1.04750 (12)	0.0532 (7)
O5	1.3926 (3)	0.12326 (16)	0.97707 (10)	0.0460 (6)
H5A	1.4998	0.0999	0.9789	0.055*
C1	0.8163 (4)	0.0628 (2)	0.90930 (13)	0.0319 (7)
C2	0.6955 (4)	0.0996 (2)	0.85929 (13)	0.0311 (7)
C3	0.5154 (5)	0.0638 (2)	0.84879 (14)	0.0404 (8)
H3	0.4795	0.0165	0.8723	0.049*
C4	0.3890 (5)	0.0955 (3)	0.80525 (16)	0.0502 (10)
H4	0.2712	0.0688	0.7983	0.060*
C5	0.4416 (5)	0.1681 (3)	0.77200 (16)	0.0536 (11)
H5	0.3564	0.1922	0.7432	0.064*
C6	0.6177 (5)	0.2053 (3)	0.78080 (15)	0.0473 (10)
H6	0.6491	0.2544	0.7578	0.057*
C7	0.7506 (4)	0.1714 (2)	0.82325 (14)	0.0354 (8)
C8	1.0119 (5)	0.2737 (2)	0.79817 (15)	0.0391 (8)
C9	1.1365 (5)	0.3380 (3)	0.82540 (16)	0.0464 (9)
H9	1.1578	0.3381	0.8647	0.056*
C10	1.2290 (6)	0.4012 (3)	0.7956 (2)	0.0625 (12)
H10	1.3126	0.4435	0.8147	0.075*
C11	1.1986 (7)	0.4023 (4)	0.7379 (2)	0.0776 (15)
H11	1.2604	0.4456	0.7175	0.093*
C12	1.0764 (6)	0.3393 (4)	0.71023 (19)	0.0752 (15)
H12	1.0554	0.3403	0.6709	0.090*
C13	0.9836 (5)	0.2743 (3)	0.73948 (16)	0.0544 (11)
H13	0.9027	0.2312	0.7200	0.065*
C14	0.8729 (4)	0.1384 (2)	1.05159 (13)	0.0323 (7)
C15	0.7840 (4)	0.2162 (2)	1.07961 (13)	0.0308 (7)
C16	0.6150 (5)	0.1969 (3)	1.10022 (14)	0.0395 (8)
H16	0.5680	0.1358	1.0971	0.047*
C17	0.5161 (5)	0.2646 (3)	1.12476 (16)	0.0454 (9)
H17	0.4044	0.2499	1.1382	0.055*
C18	0.5858 (5)	0.3544 (3)	1.12903 (16)	0.0485 (10)
H18	0.5195	0.4013	1.1451	0.058*
C19	0.7510 (5)	0.3763 (2)	1.11009 (16)	0.0441 (9)
H19	0.7934	0.4383	1.1130	0.053*
C20	0.8583 (4)	0.3083 (2)	1.08640 (14)	0.0353 (8)
C21	1.1236 (5)	0.4172 (2)	1.08019 (18)	0.0446 (9)
C22	1.2051 (5)	0.4608 (3)	1.03751 (19)	0.0583 (11)
H22	1.1940	0.4345	1.0015	0.070*
C23	1.3035 (6)	0.5441 (3)	1.0488 (2)	0.0743 (14)
H23	1.3570	0.5738	1.0200	0.089*
C24	1.3229 (6)	0.5830 (3)	1.1018 (3)	0.0756 (15)
H24	1.3891	0.6388	1.1089	0.091*
C25	1.2444 (6)	0.5391 (3)	1.1442 (2)	0.0630 (12)
H25	1.2570	0.5656	1.1802	0.076*
C26	1.1472 (5)	0.4564 (3)	1.13402 (18)	0.0520 (10)
H26	1.0968	0.4264	1.1634	0.062*
C27	1.4132 (6)	0.2166 (3)	0.95906 (19)	0.0658 (12)
H27A	1.5422	0.2292	0.9568	0.099*
H27B	1.3682	0.2592	0.9856	0.099*
H27C	1.3433	0.2252	0.9225	0.099*

	U11	U22	U33	U12	U13	U23
Cu1	0.0269 (2)	0.0242 (2)	0.0313 (2)	−0.00364 (18)	0.00475 (14)	0.00085 (17)
N1	0.0402 (18)	0.061 (2)	0.0409 (18)	−0.0093 (16)	−0.0023 (14)	0.0202 (15)
N2	0.0371 (17)	0.0344 (17)	0.080 (2)	−0.0060 (14)	0.0218 (16)	−0.0171 (16)
O1	0.0446 (15)	0.0644 (18)	0.0516 (16)	−0.0184 (14)	−0.0104 (12)	0.0285 (14)
O2	0.0358 (14)	0.0535 (15)	0.0366 (14)	−0.0067 (12)	−0.0015 (11)	0.0123 (12)
O3	0.0407 (14)	0.0362 (14)	0.0571 (16)	−0.0074 (12)	0.0189 (12)	−0.0157 (12)
O4	0.0511 (16)	0.0295 (14)	0.085 (2)	−0.0092 (13)	0.0326 (14)	−0.0149 (13)
O5	0.0321 (13)	0.0390 (14)	0.0679 (18)	−0.0078 (11)	0.0098 (12)	0.0084 (13)
C1	0.0351 (19)	0.0304 (18)	0.0307 (17)	0.0024 (16)	0.0060 (14)	−0.0032 (15)
C2	0.0326 (18)	0.0308 (18)	0.0304 (17)	0.0025 (15)	0.0059 (14)	−0.0027 (14)
C3	0.038 (2)	0.042 (2)	0.041 (2)	−0.0035 (17)	0.0059 (16)	0.0038 (17)
C4	0.032 (2)	0.068 (3)	0.049 (2)	−0.0077 (19)	−0.0012 (17)	0.006 (2)
C5	0.037 (2)	0.077 (3)	0.045 (2)	0.009 (2)	−0.0025 (17)	0.017 (2)
C6	0.041 (2)	0.056 (2)	0.045 (2)	0.0051 (19)	0.0051 (17)	0.0188 (18)
C7	0.0319 (19)	0.040 (2)	0.0345 (19)	0.0012 (16)	0.0052 (14)	0.0004 (15)
C8	0.0348 (19)	0.040 (2)	0.042 (2)	0.0010 (17)	0.0046 (16)	0.0095 (16)
C9	0.046 (2)	0.047 (2)	0.045 (2)	−0.0055 (19)	0.0005 (17)	−0.0036 (18)
C10	0.053 (3)	0.046 (3)	0.088 (4)	−0.013 (2)	0.006 (2)	0.003 (2)
C11	0.064 (3)	0.083 (4)	0.085 (4)	−0.021 (3)	0.006 (3)	0.044 (3)
C12	0.055 (3)	0.120 (4)	0.048 (3)	−0.018 (3)	0.000 (2)	0.035 (3)
C13	0.042 (2)	0.074 (3)	0.046 (2)	−0.017 (2)	0.0003 (18)	0.010 (2)
C14	0.0312 (18)	0.0302 (19)	0.0347 (19)	−0.0006 (15)	0.0004 (14)	−0.0009 (14)
C15	0.0272 (17)	0.0312 (18)	0.0335 (18)	0.0007 (14)	0.0014 (14)	−0.0026 (14)
C16	0.039 (2)	0.035 (2)	0.045 (2)	−0.0044 (16)	0.0083 (16)	−0.0021 (16)
C17	0.035 (2)	0.045 (2)	0.060 (2)	−0.0055 (18)	0.0168 (18)	−0.0112 (19)
C18	0.033 (2)	0.047 (2)	0.066 (3)	0.0111 (18)	0.0081 (18)	−0.014 (2)
C19	0.035 (2)	0.0287 (19)	0.068 (3)	0.0007 (16)	0.0032 (18)	−0.0070 (17)
C20	0.0268 (18)	0.0327 (19)	0.046 (2)	0.0006 (15)	0.0031 (15)	−0.0048 (16)
C21	0.0280 (19)	0.0310 (19)	0.075 (3)	−0.0015 (16)	0.0094 (18)	−0.0045 (18)
C22	0.047 (2)	0.052 (3)	0.074 (3)	−0.005 (2)	0.003 (2)	0.006 (2)
C23	0.058 (3)	0.056 (3)	0.107 (4)	−0.018 (2)	0.003 (3)	0.027 (3)
C24	0.057 (3)	0.037 (2)	0.128 (5)	−0.011 (2)	−0.007 (3)	−0.003 (3)
C25	0.043 (2)	0.048 (3)	0.096 (4)	0.000 (2)	0.001 (2)	−0.023 (2)
C26	0.037 (2)	0.044 (2)	0.077 (3)	−0.0041 (19)	0.0122 (19)	−0.012 (2)
C27	0.074 (3)	0.046 (2)	0.077 (3)	−0.016 (2)	0.007 (2)	0.014 (2)

Cu1—O4i	1.951 (2)	C9—H9	0.9300
Cu1—O1i	1.954 (2)	C10—C11	1.365 (6)
Cu1—O3	1.959 (2)	C10—H10	0.9300
Cu1—O2	1.967 (2)	C11—C12	1.367 (6)
Cu1—O5	2.159 (2)	C11—H11	0.9300
Cu1—Cu1i	2.5774 (10)	C12—C13	1.379 (5)
N1—C7	1.377 (4)	C12—H12	0.9300
N1—C8	1.402 (4)	C13—H13	0.9300
N1—H1	0.8314	C14—C15	1.477 (4)
N2—C20	1.375 (4)	C15—C16	1.402 (4)
N2—C21	1.413 (4)	C15—C20	1.413 (4)
N2—H2	0.8323	C16—C17	1.371 (5)
O1—C1	1.254 (4)	C16—H16	0.9300
O1—Cu1i	1.954 (2)	C17—C18	1.368 (5)
O2—C1	1.263 (4)	C17—H17	0.9300
O3—C14	1.266 (4)	C18—C19	1.366 (5)
O4—C14	1.255 (4)	C18—H18	0.9300
O4—Cu1i	1.951 (2)	C19—C20	1.400 (5)
O5—C27	1.404 (4)	C19—H19	0.9300
O5—H5A	0.8409	C21—C22	1.383 (5)
C1—C2	1.483 (4)	C21—C26	1.388 (5)
C2—C3	1.394 (5)	C22—C23	1.387 (6)
C2—C7	1.420 (4)	C22—H22	0.9300
C3—C4	1.371 (5)	C23—C24	1.368 (7)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.380 (5)	C24—C25	1.369 (6)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.373 (5)	C25—C26	1.374 (5)
C5—H5	0.9300	C25—H25	0.9300
C6—C7	1.392 (5)	C26—H26	0.9300
C6—H6	0.9300	C27—H27A	0.9600
C8—C9	1.386 (5)	C27—H27B	0.9600
C8—C13	1.387 (5)	C27—H27C	0.9600
C9—C10	1.369 (5)
O4i—Cu1—O1i	87.77 (12)	C11—C10—H10	120.0
O4i—Cu1—O3	169.37 (10)	C9—C10—H10	120.0
O1i—Cu1—O3	90.61 (12)	C10—C11—C12	119.4 (4)
O4i—Cu1—O2	90.93 (12)	C10—C11—H11	120.3
O1i—Cu1—O2	169.23 (10)	C12—C11—H11	120.3
O3—Cu1—O2	88.69 (11)	C11—C12—C13	121.3 (4)
O4i—Cu1—O5	91.53 (10)	C11—C12—H12	119.3
O1i—Cu1—O5	91.52 (10)	C13—C12—H12	119.3
O3—Cu1—O5	99.02 (10)	C12—C13—C8	119.6 (4)
O2—Cu1—O5	99.21 (10)	C12—C13—H13	120.2
O4i—Cu1—Cu1i	82.43 (8)	C8—C13—H13	120.2
O1i—Cu1—Cu1i	83.02 (8)	O4—C14—O3	123.1 (3)
O3—Cu1—Cu1i	86.94 (7)	O4—C14—C15	116.9 (3)
O2—Cu1—Cu1i	86.21 (7)	O3—C14—C15	120.0 (3)
O5—Cu1—Cu1i	171.98 (7)	C16—C15—C20	118.5 (3)
C7—N1—C8	129.6 (3)	C16—C15—C14	117.5 (3)
C7—N1—H1	116.6	C20—C15—C14	124.0 (3)
C8—N1—H1	113.4	C17—C16—C15	122.6 (3)
C20—N2—C21	125.9 (3)	C17—C16—H16	118.7
C20—N2—H2	117.8	C15—C16—H16	118.7
C21—N2—H2	116.2	C18—C17—C16	118.4 (3)
C1—O1—Cu1i	126.2 (2)	C18—C17—H17	120.8
C1—O2—Cu1	121.6 (2)	C16—C17—H17	120.8
C14—O3—Cu1	120.8 (2)	C19—C18—C17	121.2 (3)
C14—O4—Cu1i	126.8 (2)	C19—C18—H18	119.4
C27—O5—Cu1	127.4 (2)	C17—C18—H18	119.4
C27—O5—H5A	104.8	C18—C19—C20	122.0 (3)
Cu1—O5—H5A	127.6	C18—C19—H19	119.0
O1—C1—O2	122.8 (3)	C20—C19—H19	119.0
O1—C1—C2	116.5 (3)	N2—C20—C19	121.0 (3)
O2—C1—C2	120.6 (3)	N2—C20—C15	121.7 (3)
C3—C2—C7	118.6 (3)	C19—C20—C15	117.3 (3)
C3—C2—C1	117.6 (3)	C22—C21—C26	119.0 (4)
C7—C2—C1	123.7 (3)	C22—C21—N2	119.5 (4)
C4—C3—C2	122.6 (3)	C26—C21—N2	121.5 (4)
C4—C3—H3	118.7	C21—C22—C23	119.6 (4)
C2—C3—H3	118.7	C21—C22—H22	120.2
C3—C4—C5	118.2 (3)	C23—C22—H22	120.2
C3—C4—H4	120.9	C24—C23—C22	120.9 (5)
C5—C4—H4	120.9	C24—C23—H23	119.6
C6—C5—C4	121.1 (3)	C22—C23—H23	119.6
C6—C5—H5	119.5	C23—C24—C25	119.6 (4)
C4—C5—H5	119.5	C23—C24—H24	120.2
C5—C6—C7	121.6 (4)	C25—C24—H24	120.2
C5—C6—H6	119.2	C24—C25—C26	120.5 (5)
C7—C6—H6	119.2	C24—C25—H25	119.7
N1—C7—C6	121.1 (3)	C26—C25—H25	119.7
N1—C7—C2	121.1 (3)	C25—C26—C21	120.4 (4)
C6—C7—C2	117.7 (3)	C25—C26—H26	119.8
C9—C8—C13	118.2 (3)	C21—C26—H26	119.8
C9—C8—N1	118.5 (3)	O5—C27—H27A	109.5
C13—C8—N1	123.1 (3)	O5—C27—H27B	109.5
C10—C9—C8	121.4 (4)	H27A—C27—H27B	109.5
C10—C9—H9	119.3	O5—C27—H27C	109.5
C8—C9—H9	119.3	H27A—C27—H27C	109.5
C11—C10—C9	120.1 (4)	H27B—C27—H27C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.83	2.04	2.690 (4)	135
N2—H2···O3	0.83	2.05	2.688 (4)	133
O5—H5A···O1ii	0.84	2.54	3.306 (4)	152
O5—H5A···O4ii	0.84	2.55	3.260 (4)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.83	2.04	2.690 (4)	135
N2—H2⋯O3	0.83	2.05	2.688 (4)	133
O5—H5A⋯O1i	0.84	2.54	3.306 (4)	152
O5—H5A⋯O4i	0.84	2.55	3.260 (4)	143

Symmetry code: (i) .