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The title complex, [Cu
2(C
2H
3O
2)
4(C
7H
6N
2)
2], shows a binuclear cage structure having an inversion centre. There are intramolecular N-H
O hydrogen bonds between the 7-azaindole ligands and the bridging acetate O atoms.
Supporting information
CCDC reference: 145637
1-Propanol (10 ml) solutions of copper(II) acetate monohydrate (0.5 mmol) and
7-azaindole (1 mmol) were mixed and filtered. From the light blue–green
filtrate, crystals of the title compound, [Cu2(CH3COO)4(Haz)2], were
obtained.
The positional parameters of all the H atoms were calculated geometrically and
fixed with U(H) = 1.2Ueq(parent atom).
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.
Crystal data top
[Cu2(C2H3O2)4(C7H6N2)2] | Dx = 1.642 Mg m−3 |
Mr = 599.55 | Mo Kα radiation, λ = 0.71073 Å |
Monoclinic, P21/a | Cell parameters from 25 reflections |
a = 7.453 (5) Å | θ = 10–15° |
b = 14.911 (5) Å | µ = 1.81 mm−1 |
c = 11.458 (5) Å | T = 298 K |
β = 107.75 (4)° | Prism, green |
V = 1212.7 (10) Å3 | 0.2 × 0.1 × 0.1 mm |
Z = 2 | |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.035 |
θ–2θ scans | θmax = 27.5° |
Absorption correction: integration (Coppens et al., 1965) | h = 0→10 |
Tmin = 0.745, Tmax = 0.854 | k = −19→0 |
3109 measured reflections | l = −15→15 |
2779 independent reflections | 3 standard reflections every 150 reflections |
1860 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.1(Fo2 + 2Fc2)/3)2] |
wR(F2) = 0.148 | (Δ/σ)max = 0.007 |
S = 0.93 | Δρmax = 0.56 e Å−3 |
2779 reflections | Δρmin = −0.38 e Å−3 |
163 parameters | |
Crystal data top
[Cu2(C2H3O2)4(C7H6N2)2] | V = 1212.7 (10) Å3 |
Mr = 599.55 | Z = 2 |
Monoclinic, P21/a | Mo Kα radiation |
a = 7.453 (5) Å | µ = 1.81 mm−1 |
b = 14.911 (5) Å | T = 298 K |
c = 11.458 (5) Å | 0.2 × 0.1 × 0.1 mm |
β = 107.75 (4)° | |
Data collection top
Rigaku AFC-7R diffractometer | 1860 reflections with I > 2σ(I) |
Absorption correction: integration (Coppens et al., 1965) | Rint = 0.035 |
Tmin = 0.745, Tmax = 0.854 | 3 standard reflections every 150 reflections |
3109 measured reflections | intensity decay: none |
2779 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.041 | 163 parameters |
wR(F2) = 0.148 | H-atom parameters not refined |
S = 0.93 | Δρmax = 0.56 e Å−3 |
2779 reflections | Δρmin = −0.38 e Å−3 |
Special details top
Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The
weighted R-factor (wR) and goodness of fit (S) are based
on F2. R-factor (gt) are based on F. The threshold
expression of F2 > 2.0 σ(F2) is used only for calculating
R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.93853 (7) | 0.01409 (4) | 0.09550 (5) | 0.0297 (1) | |
O1 | 0.7752 (4) | 0.1007 (2) | −0.0191 (3) | 0.0426 (9) | |
O2 | 0.8780 (5) | 0.0784 (2) | −0.1804 (3) | 0.0484 (10) | |
O3 | 0.7574 (5) | −0.0827 (2) | 0.0243 (3) | 0.047 (1) | |
O4 | 0.8539 (4) | −0.1045 (2) | −0.1385 (3) | 0.0448 (10) | |
N1 | 0.8284 (5) | 0.0445 (3) | 0.2466 (3) | 0.039 (1) | |
N2 | 1.0966 (6) | 0.1248 (3) | 0.3716 (4) | 0.050 (1) | |
C1 | 0.7778 (6) | 0.1172 (3) | −0.1265 (4) | 0.038 (1) | |
C2 | 0.6487 (8) | 0.1906 (4) | −0.1947 (5) | 0.060 (2) | |
C3 | 0.7489 (6) | −0.1217 (3) | −0.0733 (4) | 0.036 (1) | |
C4 | 0.6055 (7) | −0.1949 (4) | −0.1163 (5) | 0.052 (2) | |
C5 | 0.6578 (7) | 0.0135 (3) | 0.2439 (4) | 0.043 (1) | |
C6 | 0.5821 (8) | 0.0244 (4) | 0.3399 (5) | 0.051 (2) | |
C7 | 0.6844 (8) | 0.0674 (4) | 0.4461 (5) | 0.055 (2) | |
C8 | 0.8606 (8) | 0.0989 (3) | 0.4528 (4) | 0.046 (1) | |
C9 | 1.0095 (9) | 0.1459 (4) | 0.5410 (5) | 0.062 (2) | |
C10 | 1.1460 (9) | 0.1614 (4) | 0.4881 (5) | 0.062 (2) | |
C11 | 0.9241 (6) | 0.0866 (3) | 0.3497 (4) | 0.037 (1) | |
H1 | 1.1708 | 0.1262 | 0.3163 | 0.0605* | |
H2 | 0.6807 | 0.2459 | −0.1503 | 0.0723* | |
H3 | 0.6627 | 0.1974 | −0.2747 | 0.0723* | |
H4 | 0.5205 | 0.1752 | −0.2023 | 0.0723* | |
H5 | 0.4816 | −0.1708 | −0.1290 | 0.0628* | |
H6 | 0.6145 | −0.2193 | −0.1919 | 0.0628* | |
H7 | 0.6289 | −0.2414 | −0.0556 | 0.0628* | |
H8 | 0.5845 | −0.0179 | 0.1720 | 0.0511* | |
H9 | 0.4583 | 0.0019 | 0.3324 | 0.0609* | |
H10 | 0.6339 | 0.0751 | 0.5132 | 0.0656* | |
H11 | 1.0119 | 0.1631 | 0.6222 | 0.0744* | |
H12 | 1.2609 | 0.1932 | 0.5260 | 0.0741* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0322 (3) | 0.0277 (3) | 0.0299 (3) | −0.0004 (2) | 0.0105 (2) | 0.0001 (2) |
O1 | 0.046 (2) | 0.040 (2) | 0.040 (2) | 0.010 (1) | 0.010 (1) | 0.003 (1) |
O2 | 0.056 (2) | 0.047 (2) | 0.041 (2) | 0.014 (2) | 0.013 (2) | 0.011 (2) |
O3 | 0.048 (2) | 0.045 (2) | 0.052 (2) | −0.013 (2) | 0.020 (2) | −0.003 (2) |
O4 | 0.041 (2) | 0.047 (2) | 0.046 (2) | −0.013 (1) | 0.013 (1) | −0.004 (2) |
N1 | 0.037 (2) | 0.046 (2) | 0.033 (2) | 0.003 (2) | 0.010 (2) | 0.001 (2) |
N2 | 0.045 (2) | 0.061 (3) | 0.043 (2) | −0.010 (2) | 0.009 (2) | −0.008 (2) |
C1 | 0.037 (2) | 0.029 (2) | 0.039 (2) | 0.003 (2) | −0.001 (2) | −0.002 (2) |
C2 | 0.059 (3) | 0.052 (3) | 0.057 (3) | 0.015 (3) | −0.001 (3) | 0.012 (3) |
C3 | 0.034 (2) | 0.029 (2) | 0.041 (3) | 0.000 (2) | 0.005 (2) | 0.003 (2) |
C4 | 0.049 (3) | 0.042 (3) | 0.062 (3) | −0.015 (2) | 0.010 (2) | 0.002 (2) |
C5 | 0.039 (2) | 0.048 (3) | 0.040 (2) | 0.000 (2) | 0.010 (2) | 0.005 (2) |
C6 | 0.051 (3) | 0.058 (3) | 0.052 (3) | −0.003 (2) | 0.028 (2) | 0.000 (3) |
C7 | 0.074 (4) | 0.055 (3) | 0.047 (3) | 0.007 (3) | 0.037 (3) | 0.002 (2) |
C8 | 0.066 (3) | 0.039 (3) | 0.033 (2) | 0.005 (2) | 0.016 (2) | −0.001 (2) |
C9 | 0.084 (4) | 0.059 (4) | 0.040 (3) | 0.002 (3) | 0.015 (3) | −0.013 (3) |
C10 | 0.067 (4) | 0.054 (4) | 0.051 (3) | −0.013 (3) | −0.002 (3) | −0.015 (3) |
C11 | 0.048 (3) | 0.029 (2) | 0.035 (2) | 0.000 (2) | 0.012 (2) | 0.000 (2) |
Geometric parameters (Å, º) top
Cu1—Cu1i | 2.651 (1) | C2—H3 | 0.960 |
Cu1—O1 | 1.974 (3) | C2—H4 | 0.960 |
Cu1—O2i | 1.976 (3) | C3—C4 | 1.502 (6) |
Cu1—O3 | 1.975 (3) | C4—H5 | 0.960 |
Cu1—O4i | 1.997 (3) | C4—H6 | 0.960 |
Cu1—N1 | 2.177 (4) | C4—H7 | 0.960 |
O1—C1 | 1.261 (6) | C5—C6 | 1.390 (7) |
O2—C1 | 1.248 (6) | C5—H8 | 0.960 |
O3—C3 | 1.245 (6) | C6—C7 | 1.382 (8) |
O4—C3 | 1.262 (6) | C6—H9 | 0.960 |
N1—C5 | 1.345 (6) | C7—C8 | 1.375 (8) |
N1—C11 | 1.336 (6) | C7—H10 | 0.960 |
N2—C10 | 1.383 (7) | C8—C9 | 1.435 (7) |
N2—C11 | 1.357 (6) | C8—C11 | 1.413 (7) |
N2—H1 | 0.960 | C9—C10 | 1.353 (9) |
C1—C2 | 1.509 (6) | C9—H11 | 0.960 |
C2—H2 | 0.960 | C10—H12 | 0.960 |
| | | |
Cu1···Cu1i | 2.651 (1) | C3···C6iv | 3.596 (7) |
O1···C4ii | 3.413 (6) | C4···C5iv | 3.400 (8) |
O4···C4iii | 3.497 (6) | C4···C6iv | 3.578 (8) |
O4···C6iv | 3.569 (7) | C8···C8v | 3.579 (10) |
C3···C5iv | 3.464 (7) | | |
| | | |
Cu1i—Cu1—O1 | 81.5 (1) | H2—C2—H4 | 109.5 |
Cu1i—Cu1—O2i | 86.2 (1) | H3—C2—H4 | 109.5 |
Cu1i—Cu1—O3 | 84.7 (1) | O3—C3—O4 | 124.5 (4) |
Cu1i—Cu1—O4i | 82.8 (1) | O3—C3—C4 | 118.1 (4) |
Cu1i—Cu1—N1 | 176.5 (1) | O4—C3—C4 | 117.4 (4) |
O1—Cu1—O2i | 167.8 (1) | C3—C4—H5 | 109.5 |
O1—Cu1—O3 | 89.9 (2) | C3—C4—H6 | 109.5 |
O1—Cu1—O4i | 89.8 (1) | C3—C4—H7 | 109.5 |
O1—Cu1—N1 | 95.0 (1) | H5—C4—H6 | 109.5 |
O2i—Cu1—O3 | 88.7 (2) | H5—C4—H7 | 109.5 |
O2i—Cu1—O4i | 89.0 (2) | H6—C4—H7 | 109.5 |
O2i—Cu1—N1 | 97.2 (1) | N1—C5—C6 | 123.5 (5) |
O3—Cu1—O4i | 167.4 (1) | N1—C5—H8 | 118.3 |
O3—Cu1—N1 | 96.0 (2) | C6—C5—H8 | 118.3 |
O4i—Cu1—N1 | 96.6 (1) | C5—C6—C7 | 120.2 (5) |
Cu1—O1—C1 | 125.9 (3) | C5—C6—H9 | 119.9 |
Cu1i—O2—C1 | 120.5 (3) | C7—C6—H9 | 119.9 |
Cu1—O3—C3 | 123.6 (3) | C6—C7—C8 | 118.0 (4) |
Cu1i—O4—C3 | 124.3 (3) | C6—C7—H10 | 121.0 |
Cu1—N1—C5 | 119.6 (3) | C8—C7—H10 | 121.0 |
Cu1—N1—C11 | 124.9 (3) | C7—C8—C9 | 136.6 (5) |
C5—N1—C11 | 115.3 (4) | C7—C8—C11 | 117.8 (4) |
C10—N2—C11 | 107.6 (4) | C9—C8—C11 | 105.5 (5) |
C10—N2—H1 | 126.2 | C8—C9—C10 | 107.1 (5) |
C11—N2—H1 | 126.2 | C8—C9—H11 | 126.5 |
O1—C1—O2 | 125.6 (4) | C10—C9—H11 | 126.5 |
O1—C1—C2 | 116.7 (4) | N2—C10—C9 | 110.5 (5) |
O2—C1—C2 | 117.6 (4) | N2—C10—H12 | 124.8 |
C1—C2—H2 | 109.5 | C9—C10—H12 | 124.8 |
C1—C2—H3 | 109.5 | N1—C11—N2 | 125.5 (4) |
C1—C2—H4 | 109.5 | N1—C11—C8 | 125.2 (4) |
H2—C2—H3 | 109.5 | N2—C11—C8 | 109.3 (4) |
Symmetry codes: (i) −x+2, −y, −z; (ii) −x+3/2, y+1/2, −z; (iii) x+1/2, −y−1/2, z; (iv) −x+1, −y, −z; (v) −x+2, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1···O4i | 0.960 | 2.015 | 2.822 (6) | 140.4 |
Symmetry code: (i) −x+2, −y, −z. |
Experimental details
Crystal data |
Chemical formula | [Cu2(C2H3O2)4(C7H6N2)2] |
Mr | 599.55 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 298 |
a, b, c (Å) | 7.453 (5), 14.911 (5), 11.458 (5) |
β (°) | 107.75 (4) |
V (Å3) | 1212.7 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.81 |
Crystal size (mm) | 0.2 × 0.1 × 0.1 |
|
Data collection |
Diffractometer | Rigaku AFC-7R diffractometer |
Absorption correction | Integration (Coppens et al., 1965) |
Tmin, Tmax | 0.745, 0.854 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3109, 2779, 1860 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.148, 0.93 |
No. of reflections | 2779 |
No. of parameters | 163 |
No. of restraints | ? |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.56, −0.38 |
Selected geometric parameters (Å, º) topCu1—Cu1i | 2.651 (1) | Cu1—O3 | 1.975 (3) |
Cu1—O1 | 1.974 (3) | Cu1—O4i | 1.997 (3) |
Cu1—O2i | 1.976 (3) | Cu1—N1 | 2.177 (4) |
| | | |
O1—Cu1—O2i | 167.8 (1) | O1—C1—O2 | 125.6 (4) |
O3—Cu1—O4i | 167.4 (1) | O3—C3—O4 | 124.5 (4) |
Symmetry code: (i) −x+2, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1···O4i | 0.960 | 2.015 | 2.822 (6) | 140.4 |
Symmetry code: (i) −x+2, −y, −z. |
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The structure of the mixed-bridged binuclear copper(II) complex [Cu2(CH3COO)2(az)2(Haz)2] (Haz is 7-azaindole) was reported by Peng & Lai (1988). The structure of [Cu2(CH3COO)4(Haz)2], (I), is reported here.