Tetra­kis(μ-2-anilinobenzoato-κ²O:O′)bis­[(N,N-dimethyl­formamide-κO)copper(II)]

The title compound, [Cu₂(C₁₃H₁₀NO₂)₄(C₃H₇NO)₂], is a centrosymmetric paddle-wheel dinuclear complex. The two copper ions are bridged by four caboxylate groups, with a Cu...Cu separation of 2.6168 (7) Å. Additionally, each copper ion is coordinated by one N,N-dimethyl­formamide mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.045
• wR factor = 0.108
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT145_ALERT_4_C su on beta     Small or Missing  (x 10000) .....          4 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.82 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C25
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Cu1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART and SAINT (Siemens, 1994); data reduction: XPREP; program(s) used to solve structure: SHELXTL (Siemens, 1994); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Tetrakis(µ-2-anilinobenzoato-κ²O:O')bis[(N,N'-dimethylformamide- κO)copper(II)]

Crystal data

[Cu2(C13H10NO2)4(C3H7NO)2]	F(000) = 1164
Mr = 1122.15	Dx = 1.378 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6218 reflections
a = 14.1539 (3) Å	θ = 1.7–25.7°
b = 11.0440 (2) Å	µ = 0.85 mm^−1
c = 17.8517 (1) Å	T = 298 K
β = 104.2397 (4)°	Prism, blue
V = 2704.76 (8) Å^3	0.20 × 0.15 × 0.12 mm
Z = 2

Data collection

Siemens SMART CCD diffractometer	5115 independent reflections
Radiation source: fine-focus sealed tube	3784 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω scans	θmax = 25.7°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.868, Tmax = 0.903	k = −13→13
14382 measured reflections	l = −11→21

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) = 0.108	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0371P)^2 + 2.0208P] where P = (Fo^2 + 2Fc^2)/3
5115 reflections	(Δ/σ)max < 0.001
345 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.35 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	0.04042 (3)	0.43490 (3)	0.06066 (2)	0.03512 (12)
O1	0.02261 (18)	0.58387 (19)	0.11533 (12)	0.0532 (6)
O2	−0.04433 (17)	0.69665 (19)	0.01263 (12)	0.0489 (6)
O3	0.09537 (16)	0.6088 (2)	−0.05745 (13)	0.0509 (6)
O4	0.16428 (16)	0.4985 (2)	0.04613 (13)	0.0524 (6)
O5	0.10172 (18)	0.3407 (2)	0.16674 (13)	0.0563 (6)
N1	0.0317 (2)	0.6693 (3)	0.25490 (16)	0.0597 (8)
H1	0.0177	0.6057	0.2266	0.072*
N2	0.2083 (2)	0.7233 (3)	−0.13236 (16)	0.0552 (8)
H2	0.1518	0.7239	−0.1225	0.066*
N3	0.1792 (2)	0.1799 (3)	0.23311 (19)	0.0640 (9)
C1	−0.0131 (2)	0.6826 (3)	0.08482 (19)	0.0423 (7)
C2	−0.0204 (2)	0.7865 (3)	0.13647 (18)	0.0433 (7)
C3	−0.0523 (3)	0.8970 (3)	0.1017 (2)	0.0585 (10)
H3	−0.0662	0.9033	0.0482	0.070*
C4	−0.0639 (3)	0.9974 (3)	0.1446 (2)	0.0749 (12)
H4	−0.0853	1.0705	0.1204	0.090*
C5	−0.0429 (3)	0.9875 (4)	0.2242 (3)	0.0743 (12)
H5	−0.0508	1.0545	0.2536	0.089*
C6	−0.0109 (3)	0.8811 (3)	0.2603 (2)	0.0599 (10)
H6	0.0024	0.8769	0.3140	0.072*
C7	0.0024 (2)	0.7777 (3)	0.21820 (19)	0.0462 (8)
C8	0.0813 (3)	0.6485 (3)	0.33239 (18)	0.0504 (8)
C9	0.1508 (3)	0.7267 (3)	0.3750 (2)	0.0579 (9)
H9	0.1622	0.8006	0.3539	0.069*
C10	0.2029 (3)	0.6960 (4)	0.4480 (2)	0.0730 (12)
H10	0.2489	0.7497	0.4761	0.088*
C11	0.1879 (4)	0.5872 (5)	0.4798 (3)	0.0877 (14)
H11	0.2240	0.5662	0.5290	0.105*
C12	0.1193 (4)	0.5097 (5)	0.4386 (3)	0.0944 (15)
H12	0.1083	0.4360	0.4602	0.113*
C13	0.0658 (3)	0.5396 (4)	0.3651 (2)	0.0754 (12)
H13	0.0193	0.4859	0.3377	0.091*
C14	0.1695 (2)	0.5694 (3)	−0.00796 (17)	0.0405 (7)
C15	0.2681 (2)	0.6110 (3)	−0.01276 (18)	0.0415 (7)
C16	0.3476 (2)	0.5714 (3)	0.04471 (19)	0.0528 (9)
H16	0.3365	0.5220	0.0838	0.063*
C17	0.4421 (3)	0.6027 (4)	0.0457 (2)	0.0684 (11)
H17	0.4940	0.5772	0.0854	0.082*
C18	0.4574 (3)	0.6733 (4)	−0.0143 (2)	0.0678 (11)
H18	0.5208	0.6944	−0.0149	0.081*
C19	0.3821 (2)	0.7129 (3)	−0.0723 (2)	0.0546 (9)
H19	0.3952	0.7598	−0.1119	0.065*
C20	0.2854 (2)	0.6840 (3)	−0.07345 (18)	0.0439 (7)
C21	0.2123 (2)	0.7624 (3)	−0.20698 (19)	0.0465 (8)
C22	0.2676 (3)	0.8589 (4)	−0.2212 (2)	0.0670 (11)
H22	0.3066	0.9018	−0.1803	0.080*
C23	0.2647 (3)	0.8914 (4)	−0.2968 (3)	0.0774 (13)
H23	0.3032	0.9553	−0.3058	0.093*
C24	0.2081 (4)	0.8331 (5)	−0.3570 (3)	0.0845 (14)
H24	0.2079	0.8554	−0.4072	0.101*
C25	0.1500 (4)	0.7399 (4)	−0.3436 (3)	0.0994 (17)
H25	0.1086	0.7004	−0.3848	0.119*
C26	0.1535 (3)	0.7057 (4)	−0.2695 (2)	0.0733 (12)
H26	0.1147	0.6416	−0.2612	0.088*
C27	0.1280 (3)	0.2342 (3)	0.1703 (2)	0.0549 (9)
H27	0.1105	0.1885	0.1253	0.066*
C28	0.2127 (4)	0.2477 (5)	0.3032 (3)	0.114 (2)
H28A	0.1800	0.3245	0.2984	0.171*
H28B	0.2818	0.2605	0.3126	0.171*
H28C	0.1989	0.2034	0.3456	0.171*
C29	0.2090 (3)	0.0541 (4)	0.2321 (3)	0.0990 (17)
H29A	0.1776	0.0069	0.2641	0.149*
H29B	0.2784	0.0484	0.2514	0.149*
H29C	0.1907	0.0240	0.1801	0.149*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0396 (2)	0.0335 (2)	0.0311 (2)	0.00152 (17)	0.00665 (14)	0.00230 (16)
O1	0.0789 (17)	0.0387 (13)	0.0383 (12)	0.0106 (12)	0.0071 (11)	−0.0041 (10)
O2	0.0639 (15)	0.0424 (13)	0.0376 (13)	0.0086 (11)	0.0073 (11)	−0.0047 (10)
O3	0.0398 (13)	0.0590 (14)	0.0544 (14)	−0.0029 (11)	0.0125 (11)	0.0133 (11)
O4	0.0437 (13)	0.0605 (15)	0.0520 (14)	−0.0056 (11)	0.0100 (11)	0.0153 (12)
O5	0.0738 (17)	0.0486 (14)	0.0429 (13)	0.0076 (12)	0.0076 (12)	0.0125 (11)
N1	0.084 (2)	0.0484 (17)	0.0430 (17)	−0.0040 (16)	0.0075 (15)	−0.0089 (14)
N2	0.0450 (17)	0.071 (2)	0.0517 (18)	0.0039 (14)	0.0163 (14)	0.0145 (15)
N3	0.062 (2)	0.060 (2)	0.069 (2)	0.0070 (16)	0.0136 (17)	0.0297 (17)
C1	0.0395 (17)	0.0409 (18)	0.0459 (19)	−0.0003 (14)	0.0095 (14)	−0.0068 (15)
C2	0.0380 (17)	0.0417 (18)	0.0482 (19)	0.0011 (14)	0.0067 (14)	−0.0085 (15)
C3	0.062 (2)	0.050 (2)	0.057 (2)	0.0102 (17)	0.0039 (18)	−0.0090 (17)
C4	0.087 (3)	0.050 (2)	0.076 (3)	0.023 (2)	−0.002 (2)	−0.015 (2)
C5	0.078 (3)	0.065 (3)	0.074 (3)	0.020 (2)	0.006 (2)	−0.031 (2)
C6	0.063 (2)	0.064 (2)	0.053 (2)	0.0061 (19)	0.0143 (18)	−0.0200 (19)
C7	0.0425 (18)	0.052 (2)	0.0434 (19)	−0.0002 (15)	0.0083 (15)	−0.0109 (16)
C8	0.054 (2)	0.062 (2)	0.0366 (18)	−0.0007 (17)	0.0142 (16)	−0.0096 (16)
C9	0.056 (2)	0.064 (2)	0.057 (2)	−0.0042 (19)	0.0213 (19)	−0.0134 (19)
C10	0.058 (3)	0.099 (3)	0.057 (3)	−0.004 (2)	0.006 (2)	−0.022 (2)
C11	0.080 (3)	0.123 (4)	0.051 (3)	0.001 (3)	−0.001 (2)	0.005 (3)
C12	0.098 (4)	0.109 (4)	0.069 (3)	−0.012 (3)	0.006 (3)	0.033 (3)
C13	0.076 (3)	0.078 (3)	0.065 (3)	−0.022 (2)	0.004 (2)	0.008 (2)
C14	0.0440 (18)	0.0386 (16)	0.0404 (17)	−0.0019 (15)	0.0131 (14)	−0.0068 (15)
C15	0.0409 (18)	0.0439 (17)	0.0408 (18)	−0.0005 (14)	0.0118 (14)	−0.0062 (14)
C16	0.0465 (19)	0.070 (2)	0.0426 (19)	0.0019 (18)	0.0121 (15)	0.0083 (18)
C17	0.047 (2)	0.100 (3)	0.056 (2)	0.002 (2)	0.0076 (18)	0.013 (2)
C18	0.044 (2)	0.098 (3)	0.064 (3)	−0.007 (2)	0.0184 (19)	0.005 (2)
C19	0.047 (2)	0.071 (2)	0.048 (2)	−0.0061 (18)	0.0171 (17)	0.0060 (18)
C20	0.0472 (19)	0.0452 (18)	0.0410 (18)	−0.0009 (15)	0.0140 (15)	−0.0040 (15)
C21	0.0479 (19)	0.0456 (19)	0.0456 (19)	0.0056 (15)	0.0109 (16)	0.0063 (15)
C22	0.072 (3)	0.067 (3)	0.060 (2)	−0.019 (2)	0.011 (2)	0.006 (2)
C23	0.077 (3)	0.086 (3)	0.072 (3)	−0.014 (2)	0.023 (2)	0.026 (3)
C24	0.108 (4)	0.093 (3)	0.053 (3)	0.007 (3)	0.019 (3)	0.015 (2)
C25	0.144 (5)	0.079 (3)	0.060 (3)	−0.017 (3)	−0.006 (3)	0.006 (2)
C26	0.082 (3)	0.064 (3)	0.062 (3)	−0.014 (2)	−0.005 (2)	0.013 (2)
C27	0.057 (2)	0.056 (2)	0.051 (2)	0.0030 (18)	0.0121 (17)	0.0132 (18)
C28	0.153 (5)	0.099 (4)	0.067 (3)	−0.006 (4)	−0.018 (3)	0.034 (3)
C29	0.088 (3)	0.070 (3)	0.146 (5)	0.028 (3)	0.043 (3)	0.052 (3)

Geometric parameters (Å, º)

Cu1—O1	1.961 (2)	C10—C11	1.368 (6)
Cu1—O4	1.964 (2)	C10—H10	0.9300
Cu1—O2^i	1.965 (2)	C11—C12	1.366 (7)
Cu1—O3^i	1.969 (2)	C11—H11	0.9300
Cu1—O5	2.148 (2)	C12—C13	1.384 (6)
Cu1—Cu1^i	2.6168 (7)	C12—H12	0.9300
O1—C1	1.267 (4)	C13—H13	0.9300
O2—C1	1.265 (4)	C14—C15	1.492 (4)
O2—Cu1^i	1.965 (2)	C15—C16	1.394 (4)
O3—C14	1.271 (4)	C15—C20	1.419 (4)
O3—Cu1^i	1.969 (2)	C16—C17	1.377 (5)
O4—C14	1.260 (4)	C16—H16	0.9300
O5—C27	1.230 (4)	C17—C18	1.384 (5)
N1—C7	1.379 (4)	C17—H17	0.9300
N1—C8	1.408 (4)	C18—C19	1.363 (5)
N1—H1	0.8600	C18—H18	0.9300
N2—C20	1.386 (4)	C19—C20	1.402 (4)
N2—C21	1.415 (4)	C19—H19	0.9300
N2—H2	0.8600	C21—C26	1.369 (5)
N3—C27	1.319 (4)	C21—C22	1.382 (5)
N3—C28	1.435 (6)	C22—C23	1.387 (5)
N3—C29	1.453 (5)	C22—H22	0.9300
C1—C2	1.491 (4)	C23—C24	1.337 (6)
C2—C3	1.393 (5)	C23—H23	0.9300
C2—C7	1.418 (4)	C24—C25	1.374 (6)
C3—C4	1.380 (5)	C24—H24	0.9300
C3—H3	0.9300	C25—C26	1.364 (6)
C4—C5	1.382 (6)	C25—H25	0.9300
C4—H4	0.9300	C26—H26	0.9300
C5—C6	1.363 (5)	C27—H27	0.9300
C5—H5	0.9300	C28—H28A	0.9600
C6—C7	1.405 (4)	C28—H28B	0.9600
C6—H6	0.9300	C28—H28C	0.9600
C8—C13	1.378 (5)	C29—H29A	0.9600
C8—C9	1.388 (5)	C29—H29B	0.9600
C9—C10	1.373 (5)	C29—H29C	0.9600
C9—H9	0.9300
O1—Cu1—O4	89.66 (10)	C10—C11—H11	120.4
O1—Cu1—O2^i	168.52 (9)	C11—C12—C13	120.8 (5)
O4—Cu1—O2^i	90.23 (10)	C11—C12—H12	119.6
O1—Cu1—O3^i	88.63 (10)	C13—C12—H12	119.6
O4—Cu1—O3^i	168.68 (9)	C8—C13—C12	120.2 (4)
O2^i—Cu1—O3^i	89.23 (10)	C8—C13—H13	119.9
O1—Cu1—O5	92.36 (9)	C12—C13—H13	119.9
O4—Cu1—O5	96.28 (9)	O4—C14—O3	123.5 (3)
O2^i—Cu1—O5	99.06 (9)	O4—C14—C15	117.9 (3)
O3^i—Cu1—O5	94.97 (9)	O3—C14—C15	118.6 (3)
O1—Cu1—Cu1^i	82.37 (7)	C16—C15—C20	118.7 (3)
O4—Cu1—Cu1^i	85.25 (7)	C16—C15—C14	117.3 (3)
O2^i—Cu1—Cu1^i	86.18 (6)	C20—C15—C14	123.9 (3)
O3^i—Cu1—Cu1^i	83.44 (7)	C17—C16—C15	122.5 (3)
O5—Cu1—Cu1^i	174.52 (7)	C17—C16—H16	118.8
C1—O1—Cu1	126.5 (2)	C15—C16—H16	118.8
C1—O2—Cu1^i	121.9 (2)	C16—C17—C18	117.8 (3)
C14—O3—Cu1^i	124.7 (2)	C16—C17—H17	121.1
C14—O4—Cu1	123.1 (2)	C18—C17—H17	121.1
C27—O5—Cu1	124.1 (2)	C19—C18—C17	121.9 (3)
C7—N1—C8	128.9 (3)	C19—C18—H18	119.1
C7—N1—H1	115.6	C17—C18—H18	119.1
C8—N1—H1	115.6	C18—C19—C20	121.1 (3)
C20—N2—C21	127.1 (3)	C18—C19—H19	119.5
C20—N2—H2	116.4	C20—C19—H19	119.5
C21—N2—H2	116.4	N2—C20—C19	121.6 (3)
C27—N3—C28	119.9 (3)	N2—C20—C15	120.4 (3)
C27—N3—C29	121.6 (4)	C19—C20—C15	118.0 (3)
C28—N3—C29	118.3 (4)	C26—C21—C22	117.5 (3)
O2—C1—O1	123.1 (3)	C26—C21—N2	118.1 (3)
O2—C1—C2	118.4 (3)	C22—C21—N2	124.4 (3)
O1—C1—C2	118.5 (3)	C21—C22—C23	119.7 (4)
C3—C2—C7	119.0 (3)	C21—C22—H22	120.2
C3—C2—C1	117.6 (3)	C23—C22—H22	120.2
C7—C2—C1	123.4 (3)	C24—C23—C22	121.7 (4)
C4—C3—C2	121.8 (4)	C24—C23—H23	119.1
C4—C3—H3	119.1	C22—C23—H23	119.1
C2—C3—H3	119.1	C23—C24—C25	119.1 (4)
C3—C4—C5	118.8 (4)	C23—C24—H24	120.4
C3—C4—H4	120.6	C25—C24—H24	120.4
C5—C4—H4	120.6	C26—C25—C24	119.7 (4)
C6—C5—C4	121.2 (4)	C26—C25—H25	120.1
C6—C5—H5	119.4	C24—C25—H25	120.1
C4—C5—H5	119.4	C25—C26—C21	122.2 (4)
C5—C6—C7	121.3 (3)	C25—C26—H26	118.9
C5—C6—H6	119.4	C21—C26—H26	118.9
C7—C6—H6	119.4	O5—C27—N3	125.1 (4)
N1—C7—C6	121.0 (3)	O5—C27—H27	117.5
N1—C7—C2	120.9 (3)	N3—C27—H27	117.5
C6—C7—C2	118.0 (3)	N3—C28—H28A	109.5
C13—C8—C9	118.5 (3)	N3—C28—H28B	109.5
C13—C8—N1	117.8 (3)	H28A—C28—H28B	109.5
C9—C8—N1	123.5 (3)	N3—C28—H28C	109.5
C10—C9—C8	120.7 (4)	H28A—C28—H28C	109.5
C10—C9—H9	119.7	H28B—C28—H28C	109.5
C8—C9—H9	119.7	N3—C29—H29A	109.5
C11—C10—C9	120.6 (4)	N3—C29—H29B	109.5
C11—C10—H10	119.7	H29A—C29—H29B	109.5
C9—C10—H10	119.7	N3—C29—H29C	109.5
C12—C11—C10	119.3 (4)	H29A—C29—H29C	109.5
C12—C11—H11	120.4	H29B—C29—H29C	109.5

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.02	2.638 (3)	128
N2—H2···O3	0.86	2.01	2.644 (3)	129