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In the title compound, bis(μ-p-aminobenzoato-κ2O:O)bis[(N,N-dimethylformamide-κO)copper(II)], [Cu2(L)4(DMF)2]·2DMF (HL is p-amino­benzoic acid, C7H6NO2, and DMF is N,N-dimethyl­formamide, C3H7NO), two CuII cations are bridged by four L anions to form a dinuclear complex that lies on a center of inversion. The CuII cation is coordinated by four carboxyl­ate O atoms from four L anions and one O atom from a DMF molecule. A free DMF molecule is present in the asymmetric unit. The L anions and the uncoordinated DMF molecules are linked through hydrogen bonds to form a one-dimensional structure along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804034336/ng6080sup1.cif
Contains datablocks global, (I)

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804034336/ng6080Isup2.hkl
Contains datablock I

CCDC reference: 263530

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.030
  • wR factor = 0.090
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O5 - C31 .. 5.10 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N4 PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.864(10) ...... 3.00 su-Rat N1 -H1A 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.846(10) ...... 3.00 su-Rat N2 -H2B 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(3), Rep 0.864(10) ...... 3.00 su-Rat N1 -H1A 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 2.12(3), Rep 2.122(11) ...... 2.73 su-Rat H1A -O6 1.555 2.746
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 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990).

(I) top
Crystal data top
[Cu2(C7H6NO2)4(C3H7NO)2]·2C3H7NOF(000) = 1004
Mr = 963.98Dx = 1.467 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 17677 reflections
a = 12.513 (3) Åθ = 1.8–27.5°
b = 15.918 (3) ŵ = 1.05 mm1
c = 12.122 (2) ÅT = 296 K
β = 115.32 (3)°Block, blue
V = 2182.5 (9) Å30.50 × 0.33 × 0.21 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4992 independent reflections
Radiation source: rotating anode3586 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ω scanθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1614
Tmin = 0.587, Tmax = 0.803k = 200
20168 measured reflectionsl = 015
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 0.96 w = 1/[σ2(Fo2) + (0.0462P)2]
where P = (Fo2 + 2Fc2)/3
4992 reflections(Δ/σ)max = 0.001
300 parametersΔρmax = 0.46 e Å3
4 restraintsΔρmin = 0.67 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.56461 (2)0.507104 (14)0.43898 (2)0.02657 (9)
C110.69479 (19)0.29652 (13)0.66441 (19)0.0294 (5)
C120.6596 (2)0.25307 (14)0.7438 (2)0.0339 (5)
H120.59690.27390.75760.041*
C130.7148 (2)0.18081 (14)0.8020 (2)0.0370 (5)
H130.68860.15320.85350.044*
C140.8105 (2)0.14847 (13)0.7843 (2)0.0343 (5)
C150.8466 (2)0.19175 (14)0.7057 (2)0.0387 (5)
H150.91000.17140.69270.046*
C160.7897 (2)0.26419 (14)0.6469 (2)0.0357 (5)
H160.81520.29170.59490.043*
C170.63061 (18)0.37365 (13)0.60174 (18)0.0295 (5)
C210.70646 (19)0.67402 (13)0.73414 (19)0.0314 (5)
C220.6618 (2)0.70685 (14)0.8130 (2)0.0381 (5)
H220.59420.68330.81390.046*
C230.7159 (2)0.77318 (15)0.8892 (2)0.0432 (6)
H230.68330.79440.93960.052*
C240.8185 (2)0.80909 (14)0.8921 (2)0.0390 (5)
C250.8643 (2)0.77669 (15)0.8135 (2)0.0431 (6)
H250.93250.79990.81350.052*
C260.8085 (2)0.71013 (14)0.7356 (2)0.0387 (5)
H260.83980.68950.68390.046*
C270.64126 (19)0.60497 (13)0.64966 (18)0.0297 (5)
C310.5637 (2)0.56787 (16)0.2075 (2)0.0400 (6)
H310.49590.59030.20930.048*
C320.6863 (2)0.5563 (2)0.0999 (3)0.0649 (9)
H32A0.75430.58730.15410.097*
H32B0.67610.56390.01740.097*
H32C0.69760.49770.12050.097*
C330.5067 (3)0.6430 (2)0.0171 (2)0.0718 (10)
H33A0.43780.65530.02990.108*
H33B0.48320.61710.06140.108*
H33C0.54860.69410.02030.108*
C410.9239 (3)0.47321 (19)0.7871 (3)0.0627 (8)
H410.86560.51320.74790.075*
C420.9980 (3)0.3637 (2)0.9367 (3)0.0806 (10)
H42A0.95690.31140.92700.121*
H42B1.03900.37701.02190.121*
H42C1.05390.35910.90210.121*
C430.8199 (3)0.4432 (2)0.9114 (3)0.0740 (10)
H43A0.77220.48940.86550.111*
H43B0.85260.45620.99690.111*
H43C0.77210.39360.89560.111*
N10.8682 (2)0.07691 (13)0.8464 (2)0.0463 (5)
H1A0.910 (2)0.0478 (16)0.819 (3)0.072 (10)*
H1B0.835 (2)0.0426 (14)0.875 (2)0.066 (10)*
N20.8710 (2)0.87531 (16)0.9675 (2)0.0584 (6)
H2A0.9422 (13)0.890 (2)0.985 (3)0.089 (12)*
H2B0.845 (2)0.8942 (17)1.017 (2)0.066 (10)*
N30.58286 (18)0.58617 (13)0.11123 (17)0.0417 (5)
N40.9149 (2)0.42899 (14)0.8755 (2)0.0520 (5)
O10.66211 (13)0.41125 (9)0.52782 (13)0.0342 (4)
O20.54641 (13)0.39751 (10)0.62555 (14)0.0370 (4)
O30.67205 (13)0.58318 (9)0.56670 (13)0.0339 (3)
O40.55648 (14)0.57244 (10)0.66522 (13)0.0390 (4)
O50.62674 (14)0.52408 (10)0.29523 (14)0.0362 (4)
O61.0016 (2)0.46604 (16)0.7529 (3)0.0907 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03121 (15)0.02750 (14)0.02486 (13)0.00044 (12)0.01568 (10)0.00120 (11)
C110.0318 (12)0.0275 (10)0.0288 (11)0.0011 (9)0.0127 (9)0.0020 (9)
C120.0360 (13)0.0339 (11)0.0361 (12)0.0004 (10)0.0196 (11)0.0020 (10)
C130.0449 (15)0.0331 (11)0.0364 (13)0.0031 (10)0.0209 (11)0.0023 (10)
C140.0334 (13)0.0275 (11)0.0350 (12)0.0017 (9)0.0078 (10)0.0002 (9)
C150.0337 (13)0.0379 (12)0.0482 (14)0.0054 (10)0.0210 (11)0.0030 (11)
C160.0371 (14)0.0364 (12)0.0389 (13)0.0013 (10)0.0213 (11)0.0043 (10)
C170.0310 (12)0.0298 (10)0.0267 (11)0.0007 (9)0.0116 (9)0.0044 (9)
C210.0327 (12)0.0309 (11)0.0292 (11)0.0007 (9)0.0116 (10)0.0007 (9)
C220.0369 (14)0.0415 (13)0.0391 (13)0.0048 (11)0.0193 (11)0.0045 (11)
C230.0474 (15)0.0422 (14)0.0449 (14)0.0028 (12)0.0244 (12)0.0100 (11)
C240.0408 (14)0.0318 (12)0.0381 (13)0.0007 (10)0.0109 (11)0.0043 (10)
C250.0352 (14)0.0432 (13)0.0518 (15)0.0078 (11)0.0196 (12)0.0040 (12)
C260.0396 (14)0.0413 (13)0.0394 (13)0.0022 (11)0.0207 (11)0.0045 (11)
C270.0318 (12)0.0283 (10)0.0268 (11)0.0020 (9)0.0104 (9)0.0045 (9)
C310.0418 (14)0.0477 (14)0.0382 (13)0.0074 (12)0.0243 (11)0.0041 (11)
C320.0580 (19)0.097 (2)0.0549 (17)0.0168 (18)0.0385 (16)0.0200 (17)
C330.073 (2)0.092 (2)0.0536 (19)0.0271 (19)0.0306 (17)0.0353 (17)
C410.0533 (19)0.0573 (17)0.068 (2)0.0019 (15)0.0173 (16)0.0090 (15)
C420.086 (3)0.0589 (19)0.073 (2)0.0144 (18)0.0114 (19)0.0107 (17)
C430.068 (2)0.093 (3)0.065 (2)0.013 (2)0.0331 (18)0.0178 (19)
N10.0450 (14)0.0334 (11)0.0563 (14)0.0029 (10)0.0177 (11)0.0093 (10)
N20.0513 (16)0.0571 (15)0.0621 (16)0.0134 (13)0.0197 (14)0.0247 (13)
N30.0457 (12)0.0524 (12)0.0326 (10)0.0075 (10)0.0220 (9)0.0097 (9)
N40.0483 (14)0.0487 (13)0.0499 (13)0.0032 (11)0.0125 (11)0.0007 (11)
O10.0394 (9)0.0317 (8)0.0387 (8)0.0059 (7)0.0234 (8)0.0064 (7)
O20.0393 (9)0.0409 (9)0.0385 (9)0.0117 (8)0.0240 (7)0.0086 (7)
O30.0384 (9)0.0328 (8)0.0338 (8)0.0038 (7)0.0185 (7)0.0036 (7)
O40.0428 (10)0.0438 (9)0.0336 (8)0.0133 (8)0.0192 (8)0.0071 (7)
O50.0398 (9)0.0423 (9)0.0324 (8)0.0060 (7)0.0211 (7)0.0082 (7)
O60.0733 (16)0.1000 (18)0.117 (2)0.0038 (15)0.0579 (16)0.0176 (17)
Geometric parameters (Å, º) top
Cu1—O11.9627 (15)C26—H260.9300
Cu1—O2i1.9792 (15)C27—O41.265 (2)
Cu1—O31.9724 (16)C27—O31.270 (2)
Cu1—O4i1.9639 (16)C31—O51.233 (3)
Cu1—O52.2074 (15)C31—N31.320 (3)
Cu1—Cu1i2.6269 (7)C31—H310.9300
C11—C161.391 (3)C32—N31.441 (3)
C11—C121.400 (3)C32—H32A0.9600
C11—C171.486 (3)C32—H32B0.9600
C12—C131.371 (3)C32—H32C0.9600
C12—H120.9300C33—N31.448 (3)
C13—C141.401 (3)C33—H33A0.9600
C13—H130.9300C33—H33B0.9600
C14—N11.386 (3)C33—H33C0.9600
C14—C151.399 (3)C41—O61.215 (4)
C15—C161.382 (3)C41—N41.327 (4)
C15—H150.9300C41—H410.9300
C16—H160.9300C42—N41.433 (3)
C17—O21.264 (2)C42—H42A0.9600
C17—O11.272 (2)C42—H42B0.9600
C21—C261.393 (3)C42—H42C0.9600
C21—C221.398 (3)C43—N41.447 (4)
C21—C271.486 (3)C43—H43A0.9600
C22—C231.375 (3)C43—H43B0.9600
C22—H220.9300C43—H43C0.9600
C23—C241.392 (3)N1—H1A0.864 (10)
C23—H230.9300N1—H1B0.843 (10)
C24—N21.365 (3)N2—H2A0.858 (10)
C24—C251.404 (3)N2—H2B0.846 (10)
C25—C261.392 (3)O2—Cu1i1.9792 (15)
C25—H250.9300O4—Cu1i1.9639 (16)
O1—Cu1—O2i168.43 (6)C25—C26—H26119.5
O1—Cu1—O389.52 (7)C21—C26—H26119.5
O1—Cu1—O4i88.81 (7)O4—C27—O3124.4 (2)
O1—Cu1—O5100.49 (6)O4—C27—C21116.64 (18)
O2i—Cu1—O388.10 (7)O3—C27—C21119.00 (19)
O2i—Cu1—O4i91.28 (7)O5—C31—N3126.6 (2)
O2i—Cu1—O591.08 (6)O5—C31—H31116.7
O3—Cu1—O4i168.51 (6)N3—C31—H31116.7
O3—Cu1—O5101.10 (6)N3—C32—H32A109.5
O4i—Cu1—O590.37 (6)N3—C32—H32B109.5
O1—Cu1—Cu1i90.69 (4)H32A—C32—H32B109.5
O4i—Cu1—Cu1i79.36 (5)N3—C32—H32C109.5
O3—Cu1—Cu1i89.30 (4)H32A—C32—H32C109.5
O2i—Cu1—Cu1i77.97 (4)H32B—C32—H32C109.5
O5—Cu1—Cu1i164.70 (5)N3—C33—H33A109.5
C16—C11—C12117.5 (2)N3—C33—H33B109.5
C16—C11—C17122.52 (19)H33A—C33—H33B109.5
C12—C11—C17119.98 (19)N3—C33—H33C109.5
C13—C12—C11122.1 (2)H33A—C33—H33C109.5
C13—C12—H12119.0H33B—C33—H33C109.5
C11—C12—H12119.0O6—C41—N4125.6 (3)
C12—C13—C14120.3 (2)O6—C41—H41117.2
C12—C13—H13119.9N4—C41—H41117.2
C14—C13—H13119.9N4—C42—H42A109.5
N1—C14—C15121.9 (2)N4—C42—H42B109.5
N1—C14—C13120.0 (2)H42A—C42—H42B109.5
C15—C14—C13118.0 (2)N4—C42—H42C109.5
C16—C15—C14121.1 (2)H42A—C42—H42C109.5
C16—C15—H15119.5H42B—C42—H42C109.5
C14—C15—H15119.5N4—C43—H43A109.5
C15—C16—C11121.1 (2)N4—C43—H43B109.5
C15—C16—H16119.5H43A—C43—H43B109.5
C11—C16—H16119.5N4—C43—H43C109.5
O2—C17—O1124.0 (2)H43A—C43—H43C109.5
O2—C17—C11116.91 (18)H43B—C43—H43C109.5
O1—C17—C11119.10 (18)C14—N1—H1A120 (2)
C26—C21—C22117.9 (2)C14—N1—H1B122 (2)
C26—C21—C27123.0 (2)H1A—N1—H1B107 (3)
C22—C21—C27119.0 (2)C24—N2—H2A122 (2)
C23—C22—C21121.4 (2)C24—N2—H2B122 (2)
C23—C22—H22119.3H2A—N2—H2B113 (3)
C21—C22—H22119.3C31—N3—C32121.5 (2)
C22—C23—C24121.0 (2)C31—N3—C33121.8 (2)
C22—C23—H23119.5C32—N3—C33116.5 (2)
C24—C23—H23119.5C41—N4—C42120.6 (3)
N2—C24—C23120.6 (2)C41—N4—C43121.6 (3)
N2—C24—C25121.3 (2)C42—N4—C43117.8 (3)
C23—C24—C25118.2 (2)C17—O1—Cu1116.43 (13)
C26—C25—C24120.5 (2)C17—O2—Cu1i130.77 (14)
C26—C25—H25119.7C27—O3—Cu1116.98 (14)
C24—C25—H25119.7C27—O4—Cu1i129.31 (14)
C25—C26—C21120.9 (2)C31—O5—Cu1116.04 (14)
C16—C11—C12—C130.7 (3)O5—C31—N3—C321.2 (4)
C17—C11—C12—C13178.8 (2)O5—C31—N3—C33175.8 (3)
C11—C12—C13—C140.8 (3)O6—C41—N4—C422.8 (5)
C12—C13—C14—N1178.0 (2)O6—C41—N4—C43178.8 (3)
C12—C13—C14—C150.3 (3)O2—C17—O1—Cu14.4 (3)
N1—C14—C15—C16178.4 (2)C11—C17—O1—Cu1175.15 (14)
C13—C14—C15—C160.1 (3)O4i—Cu1—O1—C1775.29 (15)
C14—C15—C16—C110.2 (4)O3—Cu1—O1—C1793.34 (15)
C12—C11—C16—C150.2 (3)O2i—Cu1—O1—C1715.3 (4)
C17—C11—C16—C15179.3 (2)O5—Cu1—O1—C17165.45 (14)
C16—C11—C17—O2179.4 (2)Cu1i—Cu1—O1—C174.04 (14)
C12—C11—C17—O21.1 (3)O1—C17—O2—Cu1i1.6 (3)
C16—C11—C17—O11.0 (3)C11—C17—O2—Cu1i177.95 (13)
C12—C11—C17—O1178.45 (19)O4—C27—O3—Cu110.3 (3)
C26—C21—C22—C230.5 (3)C21—C27—O3—Cu1168.65 (14)
C27—C21—C22—C23177.2 (2)O1—Cu1—O3—C2797.07 (15)
C21—C22—C23—C241.2 (4)O4i—Cu1—O3—C2715.5 (4)
C22—C23—C24—N2179.5 (2)O2i—Cu1—O3—C2771.61 (15)
C22—C23—C24—C251.1 (4)O5—Cu1—O3—C27162.33 (14)
N2—C24—C25—C26178.8 (2)Cu1i—Cu1—O3—C276.37 (14)
C23—C24—C25—C260.4 (4)O3—C27—O4—Cu1i8.9 (3)
C24—C25—C26—C210.2 (4)C21—C27—O4—Cu1i170.08 (14)
C22—C21—C26—C250.2 (3)N3—C31—O5—Cu1179.6 (2)
C27—C21—C26—C25177.7 (2)O1—Cu1—O5—C31164.31 (17)
C26—C21—C27—O4173.6 (2)O4i—Cu1—O5—C3175.45 (18)
C22—C21—C27—O48.8 (3)O3—Cu1—O5—C31104.11 (17)
C26—C21—C27—O37.3 (3)O2i—Cu1—O5—C3115.84 (17)
C22—C21—C27—O3170.2 (2)Cu1i—Cu1—O5—C3128.0 (3)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O6ii0.86 (1)2.12 (1)2.982 (3)174 (3)
N2—H2A···N1iii0.86 (1)2.43 (2)3.165 (4)143 (3)
Symmetry codes: (ii) x+2, y1/2, z+3/2; (iii) x+2, y+1, z+2.
 

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