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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051890/kp2064sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051890/kp2064Isup2.hkl
Contains datablock I

CCDC reference: 633903

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

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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

Computing details top

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)] top
Crystal data top
[Cu2(C13H10NO2)4(C3H7NO)2]F(000) = 1164
Mr = 1122.15Dx = 1.378 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6218 reflections
a = 14.1539 (3) Åθ = 1.7–25.7°
b = 11.0440 (2) ŵ = 0.85 mm1
c = 17.8517 (1) ÅT = 298 K
β = 104.2397 (4)°Prism, blue
V = 2704.76 (8) Å30.20 × 0.15 × 0.12 mm
Z = 2
Data collection top
Siemens SMART CCD
diffractometer
5115 independent reflections
Radiation source: fine-focus sealed tube3784 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω scansθmax = 25.7°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1717
Tmin = 0.868, Tmax = 0.903k = 1313
14382 measured reflectionsl = 1121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0371P)2 + 2.0208P]
where P = (Fo2 + 2Fc2)/3
5115 reflections(Δ/σ)max < 0.001
345 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.35 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cu10.04042 (3)0.43490 (3)0.06066 (2)0.03512 (12)
O10.02261 (18)0.58387 (19)0.11533 (12)0.0532 (6)
O20.04433 (17)0.69665 (19)0.01263 (12)0.0489 (6)
O30.09537 (16)0.6088 (2)0.05745 (13)0.0509 (6)
O40.16428 (16)0.4985 (2)0.04613 (13)0.0524 (6)
O50.10172 (18)0.3407 (2)0.16674 (13)0.0563 (6)
N10.0317 (2)0.6693 (3)0.25490 (16)0.0597 (8)
H10.01770.60570.22660.072*
N20.2083 (2)0.7233 (3)0.13236 (16)0.0552 (8)
H20.15180.72390.12250.066*
N30.1792 (2)0.1799 (3)0.23311 (19)0.0640 (9)
C10.0131 (2)0.6826 (3)0.08482 (19)0.0423 (7)
C20.0204 (2)0.7865 (3)0.13647 (18)0.0433 (7)
C30.0523 (3)0.8970 (3)0.1017 (2)0.0585 (10)
H30.06620.90330.04820.070*
C40.0639 (3)0.9974 (3)0.1446 (2)0.0749 (12)
H40.08531.07050.12040.090*
C50.0429 (3)0.9875 (4)0.2242 (3)0.0743 (12)
H50.05081.05450.25360.089*
C60.0109 (3)0.8811 (3)0.2603 (2)0.0599 (10)
H60.00240.87690.31400.072*
C70.0024 (2)0.7777 (3)0.21820 (19)0.0462 (8)
C80.0813 (3)0.6485 (3)0.33239 (18)0.0504 (8)
C90.1508 (3)0.7267 (3)0.3750 (2)0.0579 (9)
H90.16220.80060.35390.069*
C100.2029 (3)0.6960 (4)0.4480 (2)0.0730 (12)
H100.24890.74970.47610.088*
C110.1879 (4)0.5872 (5)0.4798 (3)0.0877 (14)
H110.22400.56620.52900.105*
C120.1193 (4)0.5097 (5)0.4386 (3)0.0944 (15)
H120.10830.43600.46020.113*
C130.0658 (3)0.5396 (4)0.3651 (2)0.0754 (12)
H130.01930.48590.33770.091*
C140.1695 (2)0.5694 (3)0.00796 (17)0.0405 (7)
C150.2681 (2)0.6110 (3)0.01276 (18)0.0415 (7)
C160.3476 (2)0.5714 (3)0.04471 (19)0.0528 (9)
H160.33650.52200.08380.063*
C170.4421 (3)0.6027 (4)0.0457 (2)0.0684 (11)
H170.49400.57720.08540.082*
C180.4574 (3)0.6733 (4)0.0143 (2)0.0678 (11)
H180.52080.69440.01490.081*
C190.3821 (2)0.7129 (3)0.0723 (2)0.0546 (9)
H190.39520.75980.11190.065*
C200.2854 (2)0.6840 (3)0.07345 (18)0.0439 (7)
C210.2123 (2)0.7624 (3)0.20698 (19)0.0465 (8)
C220.2676 (3)0.8589 (4)0.2212 (2)0.0670 (11)
H220.30660.90180.18030.080*
C230.2647 (3)0.8914 (4)0.2968 (3)0.0774 (13)
H230.30320.95530.30580.093*
C240.2081 (4)0.8331 (5)0.3570 (3)0.0845 (14)
H240.20790.85540.40720.101*
C250.1500 (4)0.7399 (4)0.3436 (3)0.0994 (17)
H250.10860.70040.38480.119*
C260.1535 (3)0.7057 (4)0.2695 (2)0.0733 (12)
H260.11470.64160.26120.088*
C270.1280 (3)0.2342 (3)0.1703 (2)0.0549 (9)
H270.11050.18850.12530.066*
C280.2127 (4)0.2477 (5)0.3032 (3)0.114 (2)
H28A0.18000.32450.29840.171*
H28B0.28180.26050.31260.171*
H28C0.19890.20340.34560.171*
C290.2090 (3)0.0541 (4)0.2321 (3)0.0990 (17)
H29A0.17760.00690.26410.149*
H29B0.27840.04840.25140.149*
H29C0.19070.02400.18010.149*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0396 (2)0.0335 (2)0.0311 (2)0.00152 (17)0.00665 (14)0.00230 (16)
O10.0789 (17)0.0387 (13)0.0383 (12)0.0106 (12)0.0071 (11)0.0041 (10)
O20.0639 (15)0.0424 (13)0.0376 (13)0.0086 (11)0.0073 (11)0.0047 (10)
O30.0398 (13)0.0590 (14)0.0544 (14)0.0029 (11)0.0125 (11)0.0133 (11)
O40.0437 (13)0.0605 (15)0.0520 (14)0.0056 (11)0.0100 (11)0.0153 (12)
O50.0738 (17)0.0486 (14)0.0429 (13)0.0076 (12)0.0076 (12)0.0125 (11)
N10.084 (2)0.0484 (17)0.0430 (17)0.0040 (16)0.0075 (15)0.0089 (14)
N20.0450 (17)0.071 (2)0.0517 (18)0.0039 (14)0.0163 (14)0.0145 (15)
N30.062 (2)0.060 (2)0.069 (2)0.0070 (16)0.0136 (17)0.0297 (17)
C10.0395 (17)0.0409 (18)0.0459 (19)0.0003 (14)0.0095 (14)0.0068 (15)
C20.0380 (17)0.0417 (18)0.0482 (19)0.0011 (14)0.0067 (14)0.0085 (15)
C30.062 (2)0.050 (2)0.057 (2)0.0102 (17)0.0039 (18)0.0090 (17)
C40.087 (3)0.050 (2)0.076 (3)0.023 (2)0.002 (2)0.015 (2)
C50.078 (3)0.065 (3)0.074 (3)0.020 (2)0.006 (2)0.031 (2)
C60.063 (2)0.064 (2)0.053 (2)0.0061 (19)0.0143 (18)0.0200 (19)
C70.0425 (18)0.052 (2)0.0434 (19)0.0002 (15)0.0083 (15)0.0109 (16)
C80.054 (2)0.062 (2)0.0366 (18)0.0007 (17)0.0142 (16)0.0096 (16)
C90.056 (2)0.064 (2)0.057 (2)0.0042 (19)0.0213 (19)0.0134 (19)
C100.058 (3)0.099 (3)0.057 (3)0.004 (2)0.006 (2)0.022 (2)
C110.080 (3)0.123 (4)0.051 (3)0.001 (3)0.001 (2)0.005 (3)
C120.098 (4)0.109 (4)0.069 (3)0.012 (3)0.006 (3)0.033 (3)
C130.076 (3)0.078 (3)0.065 (3)0.022 (2)0.004 (2)0.008 (2)
C140.0440 (18)0.0386 (16)0.0404 (17)0.0019 (15)0.0131 (14)0.0068 (15)
C150.0409 (18)0.0439 (17)0.0408 (18)0.0005 (14)0.0118 (14)0.0062 (14)
C160.0465 (19)0.070 (2)0.0426 (19)0.0019 (18)0.0121 (15)0.0083 (18)
C170.047 (2)0.100 (3)0.056 (2)0.002 (2)0.0076 (18)0.013 (2)
C180.044 (2)0.098 (3)0.064 (3)0.007 (2)0.0184 (19)0.005 (2)
C190.047 (2)0.071 (2)0.048 (2)0.0061 (18)0.0171 (17)0.0060 (18)
C200.0472 (19)0.0452 (18)0.0410 (18)0.0009 (15)0.0140 (15)0.0040 (15)
C210.0479 (19)0.0456 (19)0.0456 (19)0.0056 (15)0.0109 (16)0.0063 (15)
C220.072 (3)0.067 (3)0.060 (2)0.019 (2)0.011 (2)0.006 (2)
C230.077 (3)0.086 (3)0.072 (3)0.014 (2)0.023 (2)0.026 (3)
C240.108 (4)0.093 (3)0.053 (3)0.007 (3)0.019 (3)0.015 (2)
C250.144 (5)0.079 (3)0.060 (3)0.017 (3)0.006 (3)0.006 (2)
C260.082 (3)0.064 (3)0.062 (3)0.014 (2)0.005 (2)0.013 (2)
C270.057 (2)0.056 (2)0.051 (2)0.0030 (18)0.0121 (17)0.0132 (18)
C280.153 (5)0.099 (4)0.067 (3)0.006 (4)0.018 (3)0.034 (3)
C290.088 (3)0.070 (3)0.146 (5)0.028 (3)0.043 (3)0.052 (3)
Geometric parameters (Å, º) top
Cu1—O11.961 (2)C10—C111.368 (6)
Cu1—O41.964 (2)C10—H100.9300
Cu1—O2i1.965 (2)C11—C121.366 (7)
Cu1—O3i1.969 (2)C11—H110.9300
Cu1—O52.148 (2)C12—C131.384 (6)
Cu1—Cu1i2.6168 (7)C12—H120.9300
O1—C11.267 (4)C13—H130.9300
O2—C11.265 (4)C14—C151.492 (4)
O2—Cu1i1.965 (2)C15—C161.394 (4)
O3—C141.271 (4)C15—C201.419 (4)
O3—Cu1i1.969 (2)C16—C171.377 (5)
O4—C141.260 (4)C16—H160.9300
O5—C271.230 (4)C17—C181.384 (5)
N1—C71.379 (4)C17—H170.9300
N1—C81.408 (4)C18—C191.363 (5)
N1—H10.8600C18—H180.9300
N2—C201.386 (4)C19—C201.402 (4)
N2—C211.415 (4)C19—H190.9300
N2—H20.8600C21—C261.369 (5)
N3—C271.319 (4)C21—C221.382 (5)
N3—C281.435 (6)C22—C231.387 (5)
N3—C291.453 (5)C22—H220.9300
C1—C21.491 (4)C23—C241.337 (6)
C2—C31.393 (5)C23—H230.9300
C2—C71.418 (4)C24—C251.374 (6)
C3—C41.380 (5)C24—H240.9300
C3—H30.9300C25—C261.364 (6)
C4—C51.382 (6)C25—H250.9300
C4—H40.9300C26—H260.9300
C5—C61.363 (5)C27—H270.9300
C5—H50.9300C28—H28A0.9600
C6—C71.405 (4)C28—H28B0.9600
C6—H60.9300C28—H28C0.9600
C8—C131.378 (5)C29—H29A0.9600
C8—C91.388 (5)C29—H29B0.9600
C9—C101.373 (5)C29—H29C0.9600
C9—H90.9300
O1—Cu1—O489.66 (10)C10—C11—H11120.4
O1—Cu1—O2i168.52 (9)C11—C12—C13120.8 (5)
O4—Cu1—O2i90.23 (10)C11—C12—H12119.6
O1—Cu1—O3i88.63 (10)C13—C12—H12119.6
O4—Cu1—O3i168.68 (9)C8—C13—C12120.2 (4)
O2i—Cu1—O3i89.23 (10)C8—C13—H13119.9
O1—Cu1—O592.36 (9)C12—C13—H13119.9
O4—Cu1—O596.28 (9)O4—C14—O3123.5 (3)
O2i—Cu1—O599.06 (9)O4—C14—C15117.9 (3)
O3i—Cu1—O594.97 (9)O3—C14—C15118.6 (3)
O1—Cu1—Cu1i82.37 (7)C16—C15—C20118.7 (3)
O4—Cu1—Cu1i85.25 (7)C16—C15—C14117.3 (3)
O2i—Cu1—Cu1i86.18 (6)C20—C15—C14123.9 (3)
O3i—Cu1—Cu1i83.44 (7)C17—C16—C15122.5 (3)
O5—Cu1—Cu1i174.52 (7)C17—C16—H16118.8
C1—O1—Cu1126.5 (2)C15—C16—H16118.8
C1—O2—Cu1i121.9 (2)C16—C17—C18117.8 (3)
C14—O3—Cu1i124.7 (2)C16—C17—H17121.1
C14—O4—Cu1123.1 (2)C18—C17—H17121.1
C27—O5—Cu1124.1 (2)C19—C18—C17121.9 (3)
C7—N1—C8128.9 (3)C19—C18—H18119.1
C7—N1—H1115.6C17—C18—H18119.1
C8—N1—H1115.6C18—C19—C20121.1 (3)
C20—N2—C21127.1 (3)C18—C19—H19119.5
C20—N2—H2116.4C20—C19—H19119.5
C21—N2—H2116.4N2—C20—C19121.6 (3)
C27—N3—C28119.9 (3)N2—C20—C15120.4 (3)
C27—N3—C29121.6 (4)C19—C20—C15118.0 (3)
C28—N3—C29118.3 (4)C26—C21—C22117.5 (3)
O2—C1—O1123.1 (3)C26—C21—N2118.1 (3)
O2—C1—C2118.4 (3)C22—C21—N2124.4 (3)
O1—C1—C2118.5 (3)C21—C22—C23119.7 (4)
C3—C2—C7119.0 (3)C21—C22—H22120.2
C3—C2—C1117.6 (3)C23—C22—H22120.2
C7—C2—C1123.4 (3)C24—C23—C22121.7 (4)
C4—C3—C2121.8 (4)C24—C23—H23119.1
C4—C3—H3119.1C22—C23—H23119.1
C2—C3—H3119.1C23—C24—C25119.1 (4)
C3—C4—C5118.8 (4)C23—C24—H24120.4
C3—C4—H4120.6C25—C24—H24120.4
C5—C4—H4120.6C26—C25—C24119.7 (4)
C6—C5—C4121.2 (4)C26—C25—H25120.1
C6—C5—H5119.4C24—C25—H25120.1
C4—C5—H5119.4C25—C26—C21122.2 (4)
C5—C6—C7121.3 (3)C25—C26—H26118.9
C5—C6—H6119.4C21—C26—H26118.9
C7—C6—H6119.4O5—C27—N3125.1 (4)
N1—C7—C6121.0 (3)O5—C27—H27117.5
N1—C7—C2120.9 (3)N3—C27—H27117.5
C6—C7—C2118.0 (3)N3—C28—H28A109.5
C13—C8—C9118.5 (3)N3—C28—H28B109.5
C13—C8—N1117.8 (3)H28A—C28—H28B109.5
C9—C8—N1123.5 (3)N3—C28—H28C109.5
C10—C9—C8120.7 (4)H28A—C28—H28C109.5
C10—C9—H9119.7H28B—C28—H28C109.5
C8—C9—H9119.7N3—C29—H29A109.5
C11—C10—C9120.6 (4)N3—C29—H29B109.5
C11—C10—H10119.7H29A—C29—H29B109.5
C9—C10—H10119.7N3—C29—H29C109.5
C12—C11—C10119.3 (4)H29A—C29—H29C109.5
C12—C11—H11120.4H29B—C29—H29C109.5
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.862.022.638 (3)128
N2—H2···O30.862.012.644 (3)129
 

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