Download citation
Download citation
link to html
The title complex, [Cu2(C7H4NO4)4(H2O)2]·2C2H6O, forms a dimer of the paddle-wheel type located on a crystallographic inversion center. The two Cu2+ cations [Cu...Cu = 2.6543 (10) Å] are connected by four 2-nitro­benzoate ligands. The apical positions of the square-pyramidal copper coordination polyhedra are occupied by the water O atoms. The two ethanol solvent mol­ecules are linked to complex mol­ecules via O—H...O hydrogen bonds, which create one-dimensional chains of R23(13) and R44(12) rings. A π–π stacking inter­action is observed between symmetry-related benzene rings of the 2-nitro­benzoate anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045296/ng2126sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045296/ng2126Isup2.hkl
Contains datablock I

CCDC reference: 630177

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.031
  • wR factor = 0.081
  • Data-to-parameter ratio = 19.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.65 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu - O1W .. 6.49 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1998); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Tetrakis(µ-2-nitrobenzoato-κ2O:O')bis[aquacopper(II)] ethanol solvate top
Crystal data top
[Cu2(C7H4NO4)4(H2O)2]·2C2H6OF(000) = 940
Mr = 919.72Dx = 1.711 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
a = 8.326 (3) ÅCell parameters from 21708 reflections
b = 20.028 (6) Åθ = 3.2–30.0°
c = 10.803 (3) ŵ = 1.29 mm1
β = 97.77 (3)°T = 100 K
V = 1784.9 (10) Å3Block, green-blue
Z = 20.59 × 0.55 × 0.48 mm
Data collection top
Kuma KM-4 CCD
diffractometer
5144 independent reflections
Radiation source: medium-focus sealed tube4424 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scansθmax = 30.0°, θmin = 3.2°
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2003)
h = 1111
Tmin = 0.494, Tmax = 0.636k = 2528
22049 measured reflectionsl = 1415
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0424P)2 + 1.2345P]
where P = (Fo2 + 2Fc2)/3
5144 reflections(Δ/σ)max = 0.001
270 parametersΔρmax = 0.62 e Å3
3 restraintsΔρmin = 0.39 e Å3
Special details top

Experimental. IR (cm-1, KBr): 3610 (sh,ν(OH)), 3491 (s,ν(OH)), 1625 (s,νa(COO), 1577 (w), 1530 (s,νa(NOO), 1487 (w), 1413 (s,νs(COO)), 1348 (s,νs(NOO)), 1306 (w), 1267 (w), 1159 (w), 1078 (w), 1039 (w), 864 (w), 839 (w), 793 (w), 783 (w), 743 (w), 703 (w), 652 (w), 492 (s); UV-VIS (nm): 716 (λ(d–d)).

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
Cu0.64057 (2)0.499545 (8)0.454909 (15)0.01055 (6)
N10.28053 (16)0.68053 (7)0.22338 (12)0.0178 (3)
N20.09068 (18)0.38054 (7)0.25129 (13)0.0228 (3)
O10.58936 (13)0.59556 (5)0.43561 (10)0.0155 (2)
O20.34781 (13)0.59799 (5)0.50880 (10)0.0143 (2)
O1W0.86484 (15)0.51320 (6)0.38329 (12)0.0225 (2)
O30.31691 (16)0.62119 (6)0.22755 (11)0.0228 (2)
O40.18168 (16)0.70557 (6)0.14186 (12)0.0284 (3)
O50.50660 (13)0.48074 (6)0.29450 (10)0.0156 (2)
O60.26610 (14)0.48510 (5)0.37038 (10)0.0161 (2)
O70.19917 (18)0.35025 (6)0.31637 (12)0.0308 (3)
O80.05209 (18)0.38324 (8)0.27126 (14)0.0379 (3)
O91.02981 (15)0.63037 (7)0.39121 (13)0.0296 (3)
H9O1.10510.62430.45010.044*
C10.46225 (18)0.62388 (7)0.45797 (13)0.0133 (3)
C20.44859 (17)0.69775 (7)0.42914 (13)0.0135 (3)
C30.36281 (18)0.72476 (7)0.32081 (14)0.0152 (3)
C40.35452 (19)0.79303 (8)0.29764 (15)0.0179 (3)
H40.29490.80980.22290.021*
C50.4349 (2)0.83628 (8)0.38555 (16)0.0206 (3)
H50.43090.88310.37130.025*
C60.5215 (2)0.81086 (8)0.49449 (15)0.0200 (3)
H60.57640.84050.55460.024*
C70.52815 (19)0.74219 (8)0.51624 (14)0.0176 (3)
H70.58750.72550.59110.021*
C80.35381 (18)0.47656 (7)0.28482 (13)0.0137 (3)
C90.26630 (18)0.45987 (7)0.15736 (13)0.0150 (3)
C100.1349 (2)0.41613 (8)0.14181 (14)0.0187 (3)
C110.0473 (2)0.40171 (8)0.02658 (16)0.0223 (3)
H110.04240.37200.01960.027*
C120.0944 (2)0.43207 (9)0.07882 (15)0.0233 (3)
H120.03720.42270.15910.028*
C130.2251 (2)0.47603 (9)0.06686 (15)0.0224 (3)
H130.25690.49640.13920.027*
C140.3098 (2)0.49043 (8)0.05091 (14)0.0186 (3)
H140.39740.52120.05830.022*
C150.9511 (3)0.69339 (11)0.40860 (18)0.0331 (4)
H15A1.03140.73010.41480.040*
H15B0.90100.69240.48660.040*
C160.8237 (2)0.70436 (11)0.29851 (19)0.0334 (4)
H16A0.87530.70810.22250.050*
H16B0.76430.74560.31060.050*
H16C0.74830.66650.29050.050*
H1W0.915 (2)0.5497 (6)0.387 (2)0.040*
H2W0.933 (2)0.4844 (9)0.369 (2)0.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.01289 (9)0.00924 (9)0.00887 (9)0.00110 (6)0.00095 (6)0.00018 (6)
N10.0197 (6)0.0180 (6)0.0151 (6)0.0021 (5)0.0002 (5)0.0010 (5)
N20.0284 (7)0.0190 (6)0.0202 (6)0.0064 (5)0.0002 (5)0.0026 (5)
O10.0183 (5)0.0104 (5)0.0172 (5)0.0009 (4)0.0010 (4)0.0006 (4)
O20.0169 (5)0.0106 (4)0.0150 (5)0.0005 (4)0.0005 (4)0.0010 (4)
O1W0.0194 (6)0.0249 (6)0.0240 (6)0.0016 (4)0.0056 (5)0.0023 (5)
O30.0327 (7)0.0146 (5)0.0198 (5)0.0005 (4)0.0014 (5)0.0012 (4)
O40.0315 (7)0.0256 (6)0.0238 (6)0.0015 (5)0.0114 (5)0.0020 (5)
O50.0181 (5)0.0153 (5)0.0122 (5)0.0004 (4)0.0024 (4)0.0013 (4)
O60.0195 (5)0.0168 (5)0.0110 (5)0.0018 (4)0.0023 (4)0.0021 (4)
O70.0427 (8)0.0220 (6)0.0258 (6)0.0012 (5)0.0020 (6)0.0046 (5)
O80.0278 (7)0.0483 (9)0.0384 (8)0.0107 (6)0.0076 (6)0.0031 (7)
O90.0182 (6)0.0387 (7)0.0302 (7)0.0008 (5)0.0026 (5)0.0065 (6)
C10.0175 (7)0.0109 (6)0.0101 (6)0.0009 (5)0.0028 (5)0.0009 (5)
C20.0147 (6)0.0105 (6)0.0156 (6)0.0002 (5)0.0026 (5)0.0010 (5)
C30.0158 (7)0.0141 (6)0.0153 (6)0.0004 (5)0.0006 (5)0.0002 (5)
C40.0193 (7)0.0152 (7)0.0189 (7)0.0019 (5)0.0022 (6)0.0035 (5)
C50.0242 (8)0.0119 (6)0.0260 (8)0.0008 (6)0.0047 (6)0.0018 (6)
C60.0238 (8)0.0128 (7)0.0228 (8)0.0023 (5)0.0012 (6)0.0030 (5)
C70.0208 (7)0.0141 (7)0.0172 (7)0.0006 (5)0.0002 (5)0.0001 (5)
C80.0198 (7)0.0088 (6)0.0109 (6)0.0007 (5)0.0031 (5)0.0004 (5)
C90.0172 (7)0.0144 (6)0.0121 (6)0.0022 (5)0.0029 (5)0.0023 (5)
C100.0216 (8)0.0172 (7)0.0166 (7)0.0005 (5)0.0007 (6)0.0018 (5)
C110.0230 (8)0.0214 (7)0.0208 (7)0.0015 (6)0.0037 (6)0.0048 (6)
C120.0254 (8)0.0260 (8)0.0163 (7)0.0042 (6)0.0049 (6)0.0053 (6)
C130.0271 (8)0.0254 (8)0.0141 (7)0.0038 (6)0.0009 (6)0.0005 (6)
C140.0200 (7)0.0204 (7)0.0147 (7)0.0007 (6)0.0004 (5)0.0006 (5)
C150.0324 (10)0.0405 (11)0.0277 (9)0.0038 (8)0.0089 (8)0.0033 (8)
C160.0316 (10)0.0351 (10)0.0353 (10)0.0068 (8)0.0111 (8)0.0120 (8)
Geometric parameters (Å, º) top
Cu—O1W2.1331 (15)C3—C41.390 (2)
Cu—O11.9746 (12)C4—C51.389 (2)
Cu—O2i1.9922 (12)C4—H40.9500
Cu—O51.9664 (12)C5—C61.391 (2)
Cu—O6i1.9657 (12)C5—H50.9500
Cu—Cui2.6543 (10)C6—C71.395 (2)
N1—O31.2259 (18)C6—H60.9500
N1—O41.2281 (18)C7—H70.9500
N1—C31.4720 (19)C8—C91.5058 (19)
N2—O71.227 (2)C9—C141.393 (2)
N2—O81.238 (2)C9—C101.394 (2)
N2—C101.470 (2)C10—C111.386 (2)
O1—C11.2527 (19)C11—C121.393 (3)
O2—C11.2726 (19)C11—H110.9500
O2—Cui1.9922 (12)C12—C131.392 (3)
O1W—H1W0.84 (1)C12—H120.9500
O1W—H2W0.84 (1)C13—C141.399 (2)
O5—C81.2651 (19)C13—H130.9500
O6—C81.2647 (19)C14—H140.9500
O6—Cui1.9657 (12)C15—C161.499 (3)
O9—C151.446 (3)C15—H15A0.9900
O9—H9O0.8400C15—H15B0.9900
C1—C21.513 (2)C16—H16A0.9800
C2—C31.395 (2)C16—H16B0.9800
C2—C71.396 (2)C16—H16C0.9800
O1—Cu—O1W91.37 (5)C4—C5—H5120.1
O2i—Cu—O1W100.11 (5)C6—C5—H5120.1
O5—Cu—O1W97.18 (6)C5—C6—C7120.51 (14)
O6i—Cu—O1W94.38 (6)C5—C6—H6119.7
O1—Cu—O2i168.45 (5)C7—C6—H6119.7
O1—Cu—O590.28 (5)C6—C7—C2120.71 (14)
O1—Cu—O6i90.04 (5)C6—C7—H7119.6
O2i—Cu—O589.56 (5)C2—C7—H7119.6
O2i—Cu—O6i87.82 (5)O6—C8—O5127.17 (13)
O5—Cu—O6i168.42 (5)O6—C8—C9116.27 (13)
O6i—Cu—Cui84.28 (4)O5—C8—C9116.56 (13)
O5—Cu—Cui84.34 (4)C14—C9—C10117.64 (14)
O1—Cu—Cui81.00 (3)C14—C9—C8120.65 (14)
O2i—Cu—Cui87.49 (3)C10—C9—C8121.64 (14)
O1W—Cu—Cui172.24 (4)C11—C10—C9123.29 (15)
O3—N1—O4124.09 (13)C11—C10—N2117.58 (15)
O3—N1—C3117.93 (13)C9—C10—N2119.06 (14)
O4—N1—C3117.97 (13)C10—C11—C12118.08 (16)
O7—N2—O8124.85 (16)C10—C11—H11121.0
O7—N2—C10117.10 (15)C12—C11—H11121.0
O8—N2—C10118.04 (15)C13—C12—C11120.22 (15)
C1—O1—Cu126.63 (10)C13—C12—H12119.9
C1—O2—Cui117.72 (9)C11—C12—H12119.9
Cu—O1W—H1W123.2 (16)C12—C13—C14120.43 (16)
Cu—O1W—H2W128.9 (17)C12—C13—H13119.8
H1W—O1W—H2W105.3 (17)C14—C13—H13119.8
C8—O5—Cu122.00 (10)C9—C14—C13120.32 (15)
C8—O6—Cui122.04 (10)C9—C14—H14119.8
C15—O9—H9O109.5C13—C14—H14119.8
O1—C1—O2126.87 (13)O9—C15—C16108.01 (16)
O1—C1—C2116.43 (13)O9—C15—H15A110.1
O2—C1—C2116.57 (13)C16—C15—H15A110.1
C3—C2—C7117.44 (13)O9—C15—H15B110.1
C3—C2—C1124.58 (13)C16—C15—H15B110.1
C7—C2—C1117.98 (13)H15A—C15—H15B108.4
C4—C3—C2122.67 (14)C15—C16—H16A109.5
C4—C3—N1117.14 (13)C15—C16—H16B109.5
C2—C3—N1120.17 (13)H16A—C16—H16B109.5
C5—C4—C3118.86 (14)C15—C16—H16C109.5
C5—C4—H4120.6H16A—C16—H16C109.5
C3—C4—H4120.6H16B—C16—H16C109.5
C4—C5—C6119.81 (14)
O6i—Cu—O1—C188.45 (12)C3—C4—C5—C60.1 (2)
O5—Cu—O1—C179.98 (12)C4—C5—C6—C70.0 (3)
O2i—Cu—O1—C19.2 (3)C5—C6—C7—C20.1 (2)
O1W—Cu—O1—C1177.17 (12)C3—C2—C7—C60.1 (2)
Cui—Cu—O1—C14.25 (11)C1—C2—C7—C6179.38 (14)
O6i—Cu—O5—C811.6 (3)Cui—O6—C8—O55.0 (2)
O1—Cu—O5—C880.00 (11)Cui—O6—C8—C9175.27 (9)
O2i—Cu—O5—C888.45 (11)Cu—O5—C8—O62.1 (2)
O1W—Cu—O5—C8171.42 (11)Cu—O5—C8—C9178.21 (9)
Cui—Cu—O5—C80.92 (11)O6—C8—C9—C14136.38 (15)
Cu—O1—C1—O27.4 (2)O5—C8—C9—C1443.4 (2)
Cu—O1—C1—C2176.92 (9)O6—C8—C9—C1040.5 (2)
Cui—O2—C1—O15.47 (19)O5—C8—C9—C10139.73 (15)
Cui—O2—C1—C2178.82 (9)C14—C9—C10—C110.3 (2)
O1—C1—C2—C398.68 (18)C8—C9—C10—C11177.26 (15)
O2—C1—C2—C385.15 (18)C14—C9—C10—N2177.06 (14)
O1—C1—C2—C780.80 (18)C8—C9—C10—N25.9 (2)
O2—C1—C2—C795.37 (17)O7—N2—C10—C11125.48 (17)
C7—C2—C3—C40.0 (2)O8—N2—C10—C1154.6 (2)
C1—C2—C3—C4179.47 (15)O7—N2—C10—C951.5 (2)
C7—C2—C3—N1178.05 (14)O8—N2—C10—C9128.45 (17)
C1—C2—C3—N11.4 (2)C9—C10—C11—C120.7 (3)
O3—N1—C3—C4163.19 (15)N2—C10—C11—C12176.16 (15)
O4—N1—C3—C415.7 (2)C10—C11—C12—C130.7 (3)
O3—N1—C3—C214.9 (2)C11—C12—C13—C140.3 (3)
O4—N1—C3—C2166.20 (15)C10—C9—C14—C131.2 (2)
C2—C3—C4—C50.1 (2)C8—C9—C14—C13178.26 (14)
N1—C3—C4—C5177.97 (14)C12—C13—C14—C91.3 (3)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H9O···O2ii0.842.102.852 (2)149
O1W—H1W···O90.84 (1)1.88 (1)2.715 (2)178 (2)
O1W—H2W···O8ii0.84 (1)2.29 (1)2.991 (2)141 (2)
Symmetry code: (ii) x+1, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds