metal-organic compounds
[μ-2,8-Dimethyl-1,4,5,6,7,10,11,12-octahydrodiimidazo[4,5-h;4′,5′-c][1,6]diazecine-5,11-diacetato]bis[diaquanitratocopper(II)] trihydrate
aDepartamento de Química Inorgánica y Nuclear, Facultad de Química, UNAM, 04510 México, DF, Mexico, and bDEP Facultad de Ciencias Químicas, UANL, Guerrero y Progreso S/N, Col. Treviño, 64570 Monterrey, NL, Mexico
*Correspondence e-mail: sylvain_bernes@hotmail.com
The title compound, [Cu2(C16H20N6O4)(NO3)2(H2O)4]·3H2O, crystallizes with two dinuclear CuII complex molecules, each lying on an inversion center, and six solvent water molecules per The central 1,6-diazecine ring adopts the common chair conformation invariably found in the family of complexes bearing such ligands. The CuII atoms have an octahedral geometry, with a very strong tetragonal distortion due to the Jahn–Teller effect. Axial sites are occupied by a nitrate ion and a water molecule. The Cu⋯Cu separations [7.3580 (9) and 7.3341 (9) Å] are compatible with a potential catecholase activity. Neighboring molecules in the are connected via O—H⋯O hydrogen bonds formed by water molecules and carboxylate O atoms. N—H⋯O hydrogen bonds are also present.
Related literature
For the X-ray characterized dinuclear CuII complexes based on related bis(aminoimidazole) ligands, which were designed as models of the catechol oxidaze active site, see: Driessen et al. (2005); Gasque et al. (2005, 2008); Mendoza-Díaz et al. (2002); Sosa et al. (2005).
Experimental
Crystal data
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Refinement
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Data collection: XSCANS (Siemens, 1996); cell XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536808023969/hy2146sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808023969/hy2146Isup2.hkl
The diazecine derivative was prepared as described previously (Mendoza-Díaz et al., 2002). To prepare the title compound, Cu(NO3)2.2.5H2O (0.232 g, 1 mmol) were dissolved in 20 ml of water, and an aqueous solution containing the ligand (0.251 g, 0.5 mmol) was added dropwise with stirring. The final pH was 2, at which the solution was left to stand. Blue crystals were collected after two days. Analysis, calculated for C16H34Cu2N8O17: C 26.05, H 4.61, N 15.20%; found: C 26.67, H 4.55, N 15.55%.
Water H atoms were located in a difference Fourier map and refined with distance restraints of O—H = 0.85 (1) and H···H = 1.34 (1) Å, and with Uiso(H) = 1.5Ueq(O). Other H atoms were positioned geometrically and refined as riding atoms, with N—H = 0.86 and C—H = 0.96 (CH3) and 0.97 Å (CH2), and with Uiso(H) = 1.2Ueq(C,N) or Uiso(H) = 1.5Ueq(methyl C).
Data collection: XSCANS (Siemens, 1996); cell
XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. Structure of the first independent molecule. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) -x, 2-y, 1-z.] | |
Fig. 2. Structure of the second independent molecule. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity. [Symmetry code: (ii) 1-x, 2-y, -z.] | |
Fig. 3. A part of the crystal packing, viewed down the [100] direction. C- and N–bonded H atoms have been omitted for clarity. Dashed lines represent hydrogen bonds involving water molecules and carboxylate O atoms. |
[Cu2(C16H20N6O4)(NO3)2(H2O)4]·3H2O | Z = 2 |
Mr = 737.59 | F(000) = 760 |
Triclinic, P1 | Dx = 1.752 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.7983 (9) Å | Cell parameters from 74 reflections |
b = 8.7523 (11) Å | θ = 3.8–12.5° |
c = 22.509 (2) Å | µ = 1.61 mm−1 |
α = 91.802 (10)° | T = 296 K |
β = 93.479 (9)° | Prism, blue |
γ = 114.023 (11)° | 0.24 × 0.20 × 0.18 mm |
V = 1398.0 (3) Å3 |
Bruker P4 diffractometer | 5139 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 27.5°, θmin = 2.6° |
2θ/ω scans | h = −9→7 |
Absorption correction: ψ scan (XSCANS; Siemens, 1996) | k = −10→11 |
Tmin = 0.638, Tmax = 0.750 | l = −29→29 |
12145 measured reflections | 3 standard reflections every 97 reflections |
6396 independent reflections | intensity decay: 2.5% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.082 | w = 1/[σ2(Fo2) + (0.0357P)2 + 0.6951P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.002 |
6396 reflections | Δρmax = 0.50 e Å−3 |
433 parameters | Δρmin = −0.48 e Å−3 |
22 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 constraints | Extinction coefficient: 0.0028 (5) |
Primary atom site location: structure-invariant direct methods |
[Cu2(C16H20N6O4)(NO3)2(H2O)4]·3H2O | γ = 114.023 (11)° |
Mr = 737.59 | V = 1398.0 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.7983 (9) Å | Mo Kα radiation |
b = 8.7523 (11) Å | µ = 1.61 mm−1 |
c = 22.509 (2) Å | T = 296 K |
α = 91.802 (10)° | 0.24 × 0.20 × 0.18 mm |
β = 93.479 (9)° |
Bruker P4 diffractometer | 5139 reflections with I > 2σ(I) |
Absorption correction: ψ scan (XSCANS; Siemens, 1996) | Rint = 0.028 |
Tmin = 0.638, Tmax = 0.750 | 3 standard reflections every 97 reflections |
12145 measured reflections | intensity decay: 2.5% |
6396 independent reflections |
R[F2 > 2σ(F2)] = 0.031 | 22 restraints |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.50 e Å−3 |
6396 reflections | Δρmin = −0.48 e Å−3 |
433 parameters |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.08644 (4) | 0.89792 (3) | 0.348009 (11) | 0.02579 (9) | |
N1 | −0.0982 (3) | 0.7671 (2) | 0.40361 (8) | 0.0248 (4) | |
C2 | −0.1523 (3) | 0.6214 (3) | 0.42879 (10) | 0.0256 (4) | |
N3 | −0.2240 (3) | 0.6329 (2) | 0.48134 (8) | 0.0258 (4) | |
H3A | −0.2680 | 0.5535 | 0.5052 | 0.031* | |
C4 | −0.2147 (3) | 0.7941 (3) | 0.49036 (9) | 0.0238 (4) | |
C5 | −0.1392 (3) | 0.8745 (3) | 0.44130 (9) | 0.0231 (4) | |
C6 | −0.0845 (3) | 1.0489 (3) | 0.42218 (9) | 0.0234 (4) | |
H6A | −0.0850 | 1.1228 | 0.4551 | 0.028* | |
H6B | −0.1710 | 1.0513 | 0.3898 | 0.028* | |
N7 | 0.1104 (3) | 1.1013 (2) | 0.40212 (8) | 0.0236 (4) | |
C8 | 0.1656 (3) | 1.2389 (3) | 0.36114 (10) | 0.0275 (5) | |
H8A | 0.2246 | 1.3460 | 0.3838 | 0.033* | |
H8B | 0.0550 | 1.2358 | 0.3380 | 0.033* | |
C9 | 0.3037 (3) | 1.2185 (3) | 0.31942 (10) | 0.0294 (5) | |
O10 | 0.2858 (2) | 1.06789 (19) | 0.30833 (7) | 0.0303 (3) | |
O11 | 0.4199 (3) | 1.3415 (2) | 0.29801 (9) | 0.0502 (5) | |
C12 | −0.1377 (4) | 0.4685 (3) | 0.40444 (12) | 0.0388 (6) | |
H12A | −0.0285 | 0.4996 | 0.3822 | 0.058* | |
H12B | −0.2484 | 0.4038 | 0.3787 | 0.058* | |
H12C | −0.1267 | 0.4028 | 0.4366 | 0.058* | |
C13 | −0.2580 (3) | 0.8638 (3) | 0.54610 (9) | 0.0262 (4) | |
H13A | −0.3785 | 0.7852 | 0.5578 | 0.031* | |
H13B | −0.2700 | 0.9673 | 0.5377 | 0.031* | |
O14 | 0.0602 (3) | 0.7270 (2) | 0.28594 (7) | 0.0337 (4) | |
H14A | −0.048 (2) | 0.651 (3) | 0.2794 (12) | 0.051* | |
H14B | 0.087 (4) | 0.770 (3) | 0.2528 (7) | 0.051* | |
O15 | −0.1735 (3) | 0.9468 (2) | 0.28392 (8) | 0.0421 (4) | |
H15A | −0.126 (4) | 0.955 (4) | 0.2509 (8) | 0.063* | |
H15B | −0.263 (3) | 0.851 (2) | 0.2816 (14) | 0.063* | |
Cu2 | 0.35494 (4) | 0.83718 (3) | 0.145370 (11) | 0.02455 (8) | |
N21 | 0.5757 (3) | 0.8507 (2) | 0.10232 (8) | 0.0246 (4) | |
C22 | 0.6423 (3) | 0.7446 (3) | 0.08044 (10) | 0.0273 (5) | |
N23 | 0.7269 (3) | 0.8023 (2) | 0.03001 (8) | 0.0258 (4) | |
H23A | 0.7806 | 0.7542 | 0.0086 | 0.031* | |
C24 | 0.7128 (3) | 0.9526 (3) | 0.01846 (9) | 0.0225 (4) | |
C25 | 0.6218 (3) | 0.9813 (3) | 0.06424 (9) | 0.0218 (4) | |
C26 | 0.5580 (3) | 1.1153 (3) | 0.08005 (9) | 0.0225 (4) | |
H26A | 0.5708 | 1.1879 | 0.0474 | 0.027* | |
H26B | 0.6314 | 1.1827 | 0.1152 | 0.027* | |
N27 | 0.3561 (2) | 1.0257 (2) | 0.09200 (7) | 0.0213 (3) | |
C28 | 0.2817 (3) | 1.1241 (3) | 0.12900 (10) | 0.0267 (5) | |
H28A | 0.2282 | 1.1836 | 0.1036 | 0.032* | |
H28B | 0.3831 | 1.2059 | 0.1552 | 0.032* | |
C29 | 0.1307 (3) | 1.0060 (3) | 0.16603 (10) | 0.0278 (5) | |
O30 | 0.1386 (2) | 0.86562 (19) | 0.17597 (7) | 0.0293 (3) | |
O31 | 0.0133 (3) | 1.0514 (2) | 0.18558 (8) | 0.0415 (4) | |
C32 | 0.6350 (4) | 0.5899 (3) | 0.10759 (12) | 0.0416 (6) | |
H32A | 0.5864 | 0.5831 | 0.1460 | 0.062* | |
H32B | 0.7595 | 0.5927 | 0.1119 | 0.062* | |
H32C | 0.5544 | 0.4937 | 0.0823 | 0.062* | |
C33 | 0.7703 (3) | 1.0501 (3) | −0.03551 (9) | 0.0248 (4) | |
H33A | 0.8968 | 1.0630 | −0.0427 | 0.030* | |
H33B | 0.7751 | 1.1612 | −0.0272 | 0.030* | |
O34 | 0.3272 (3) | 0.6462 (2) | 0.19384 (8) | 0.0351 (4) | |
H34A | 0.222 (2) | 0.564 (3) | 0.1904 (12) | 0.053* | |
H34B | 0.364 (4) | 0.668 (4) | 0.2303 (6) | 0.053* | |
O35 | 0.5368 (3) | 1.0386 (2) | 0.22603 (8) | 0.0393 (4) | |
H35A | 0.466 (3) | 1.044 (4) | 0.2520 (10) | 0.059* | |
H35B | 0.628 (3) | 1.029 (4) | 0.2450 (12) | 0.059* | |
N41 | 0.3385 (3) | 0.7364 (2) | 0.43818 (9) | 0.0332 (4) | |
O41 | 0.2854 (4) | 0.7699 (3) | 0.48506 (9) | 0.0635 (6) | |
O42 | 0.3741 (3) | 0.6098 (2) | 0.43267 (9) | 0.0426 (4) | |
O43 | 0.3583 (3) | 0.8284 (3) | 0.39489 (8) | 0.0487 (5) | |
N51 | 0.1540 (3) | 0.4932 (2) | 0.04767 (9) | 0.0320 (4) | |
O51 | 0.2721 (3) | 0.5612 (3) | 0.01204 (9) | 0.0540 (5) | |
O52 | 0.0845 (3) | 0.3372 (2) | 0.05034 (9) | 0.0449 (5) | |
O53 | 0.1045 (3) | 0.5808 (2) | 0.08235 (8) | 0.0425 (4) | |
O61 | 0.7678 (4) | 0.4526 (3) | 0.24970 (14) | 0.0846 (10) | |
H61A | 0.657 (3) | 0.398 (5) | 0.259 (2) | 0.127* | |
H61B | 0.819 (4) | 0.384 (3) | 0.250 (2) | 0.127* | |
O62 | −0.0134 (3) | 0.3570 (2) | 0.17744 (9) | 0.0484 (5) | |
H62A | −0.015 (5) | 0.260 (2) | 0.1804 (14) | 0.073* | |
H62B | −0.006 (5) | 0.371 (4) | 0.1406 (6) | 0.073* | |
O63 | 0.4948 (3) | 0.6773 (2) | 0.30304 (8) | 0.0404 (4) | |
H63A | 0.477 (5) | 0.5775 (18) | 0.3072 (14) | 0.061* | |
H63B | 0.448 (5) | 0.709 (4) | 0.3310 (11) | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.03386 (16) | 0.02060 (13) | 0.02290 (14) | 0.00971 (11) | 0.01201 (11) | 0.00325 (10) |
N1 | 0.0294 (10) | 0.0231 (9) | 0.0225 (9) | 0.0105 (8) | 0.0069 (7) | 0.0032 (7) |
C2 | 0.0292 (11) | 0.0233 (10) | 0.0246 (11) | 0.0104 (9) | 0.0057 (9) | 0.0047 (8) |
N3 | 0.0300 (10) | 0.0217 (9) | 0.0246 (9) | 0.0082 (7) | 0.0082 (7) | 0.0066 (7) |
C4 | 0.0232 (10) | 0.0216 (10) | 0.0250 (10) | 0.0069 (8) | 0.0054 (8) | 0.0026 (8) |
C5 | 0.0225 (10) | 0.0228 (10) | 0.0233 (10) | 0.0081 (8) | 0.0043 (8) | 0.0021 (8) |
C6 | 0.0256 (11) | 0.0249 (10) | 0.0220 (10) | 0.0119 (9) | 0.0060 (8) | 0.0038 (8) |
N7 | 0.0294 (10) | 0.0211 (8) | 0.0214 (9) | 0.0103 (7) | 0.0089 (7) | 0.0046 (7) |
C8 | 0.0361 (12) | 0.0221 (10) | 0.0256 (11) | 0.0117 (9) | 0.0111 (9) | 0.0064 (8) |
C9 | 0.0338 (12) | 0.0280 (11) | 0.0265 (11) | 0.0114 (10) | 0.0102 (9) | 0.0064 (9) |
O10 | 0.0363 (9) | 0.0257 (8) | 0.0298 (8) | 0.0116 (7) | 0.0150 (7) | 0.0051 (6) |
O11 | 0.0573 (12) | 0.0308 (9) | 0.0619 (13) | 0.0124 (9) | 0.0368 (10) | 0.0140 (9) |
C12 | 0.0554 (16) | 0.0271 (12) | 0.0382 (14) | 0.0197 (11) | 0.0143 (12) | 0.0054 (10) |
C13 | 0.0254 (11) | 0.0285 (11) | 0.0248 (11) | 0.0101 (9) | 0.0085 (8) | 0.0034 (8) |
O14 | 0.0437 (10) | 0.0272 (8) | 0.0259 (8) | 0.0088 (7) | 0.0127 (7) | 0.0000 (7) |
O15 | 0.0395 (11) | 0.0469 (11) | 0.0327 (9) | 0.0092 (8) | 0.0114 (8) | 0.0047 (8) |
Cu2 | 0.02862 (15) | 0.02653 (14) | 0.02214 (14) | 0.01350 (11) | 0.00965 (10) | 0.00828 (10) |
N21 | 0.0261 (9) | 0.0271 (9) | 0.0228 (9) | 0.0123 (8) | 0.0054 (7) | 0.0070 (7) |
C22 | 0.0281 (11) | 0.0315 (11) | 0.0257 (11) | 0.0148 (9) | 0.0056 (9) | 0.0064 (9) |
N23 | 0.0288 (10) | 0.0296 (9) | 0.0242 (9) | 0.0163 (8) | 0.0076 (7) | 0.0040 (7) |
C24 | 0.0211 (10) | 0.0252 (10) | 0.0218 (10) | 0.0098 (8) | 0.0032 (8) | 0.0037 (8) |
C25 | 0.0205 (10) | 0.0237 (10) | 0.0209 (10) | 0.0086 (8) | 0.0026 (8) | 0.0044 (8) |
C26 | 0.0230 (10) | 0.0224 (10) | 0.0220 (10) | 0.0085 (8) | 0.0055 (8) | 0.0035 (8) |
N27 | 0.0230 (9) | 0.0220 (8) | 0.0201 (8) | 0.0097 (7) | 0.0067 (7) | 0.0032 (7) |
C28 | 0.0314 (12) | 0.0297 (11) | 0.0243 (10) | 0.0166 (9) | 0.0099 (9) | 0.0052 (9) |
C29 | 0.0300 (12) | 0.0333 (12) | 0.0226 (11) | 0.0145 (10) | 0.0075 (9) | 0.0046 (9) |
O30 | 0.0343 (9) | 0.0302 (8) | 0.0265 (8) | 0.0146 (7) | 0.0128 (6) | 0.0076 (6) |
O31 | 0.0460 (11) | 0.0491 (11) | 0.0446 (10) | 0.0310 (9) | 0.0265 (8) | 0.0172 (8) |
C32 | 0.0576 (17) | 0.0428 (14) | 0.0415 (14) | 0.0350 (13) | 0.0172 (12) | 0.0187 (12) |
C33 | 0.0215 (10) | 0.0290 (11) | 0.0228 (10) | 0.0083 (9) | 0.0061 (8) | 0.0053 (8) |
O34 | 0.0404 (10) | 0.0308 (9) | 0.0314 (9) | 0.0109 (7) | 0.0053 (7) | 0.0111 (7) |
O35 | 0.0399 (10) | 0.0510 (11) | 0.0328 (9) | 0.0241 (9) | 0.0069 (8) | 0.0005 (8) |
N41 | 0.0346 (11) | 0.0308 (10) | 0.0348 (11) | 0.0136 (9) | 0.0039 (9) | 0.0068 (8) |
O41 | 0.1023 (19) | 0.0726 (15) | 0.0410 (12) | 0.0576 (14) | 0.0303 (12) | 0.0161 (10) |
O42 | 0.0498 (11) | 0.0284 (9) | 0.0530 (11) | 0.0177 (8) | 0.0129 (9) | 0.0093 (8) |
O43 | 0.0711 (14) | 0.0503 (11) | 0.0392 (10) | 0.0368 (11) | 0.0161 (9) | 0.0207 (9) |
N51 | 0.0358 (11) | 0.0319 (10) | 0.0311 (10) | 0.0174 (9) | −0.0023 (8) | −0.0005 (8) |
O51 | 0.0574 (13) | 0.0541 (12) | 0.0461 (12) | 0.0165 (10) | 0.0171 (10) | 0.0033 (9) |
O52 | 0.0558 (12) | 0.0292 (9) | 0.0502 (11) | 0.0183 (8) | 0.0008 (9) | 0.0021 (8) |
O53 | 0.0532 (12) | 0.0388 (10) | 0.0416 (10) | 0.0249 (9) | 0.0074 (9) | −0.0008 (8) |
O61 | 0.0627 (16) | 0.0583 (15) | 0.101 (2) | −0.0102 (12) | 0.0429 (15) | −0.0296 (15) |
O62 | 0.0574 (12) | 0.0403 (11) | 0.0497 (12) | 0.0196 (10) | 0.0189 (10) | 0.0102 (9) |
O63 | 0.0469 (11) | 0.0366 (10) | 0.0365 (10) | 0.0144 (9) | 0.0103 (8) | 0.0094 (8) |
Cu1—O10 | 1.9484 (16) | C33—N27ii | 1.514 (3) |
Cu1—O14 | 1.9533 (16) | N41—O41 | 1.226 (3) |
Cu1—N1 | 1.9789 (18) | N41—O42 | 1.251 (3) |
Cu1—N7 | 2.0619 (17) | N41—O43 | 1.260 (3) |
Cu1—O15 | 2.601 (2) | N51—O51 | 1.233 (3) |
Cu1—O43 | 2.607 (2) | N51—O52 | 1.253 (3) |
N1—C2 | 1.327 (3) | N51—O53 | 1.259 (3) |
N1—C5 | 1.390 (3) | N3—H3A | 0.8600 |
C2—N3 | 1.357 (3) | C6—H6A | 0.9700 |
C2—C12 | 1.480 (3) | C6—H6B | 0.9700 |
N3—C4 | 1.391 (3) | C8—H8A | 0.9700 |
C4—C5 | 1.361 (3) | C8—H8B | 0.9700 |
C4—C13 | 1.494 (3) | C12—H12A | 0.9600 |
C5—C6 | 1.493 (3) | C12—H12B | 0.9600 |
C6—N7 | 1.501 (3) | C12—H12C | 0.9600 |
N7—C8 | 1.477 (3) | C13—H13A | 0.9700 |
N7—C13i | 1.519 (3) | C13—H13B | 0.9700 |
C8—C9 | 1.530 (3) | O14—H14A | 0.84 (1) |
C9—O11 | 1.226 (3) | O14—H14B | 0.85 (1) |
C9—O10 | 1.282 (3) | O15—H15A | 0.84 (1) |
C13—N7i | 1.519 (3) | O15—H15B | 0.84 (1) |
Cu2—O30 | 1.9632 (15) | N23—H23A | 0.8600 |
Cu2—O34 | 1.9697 (17) | C26—H26A | 0.9700 |
Cu2—N21 | 1.9903 (18) | C26—H26B | 0.9700 |
Cu2—N27 | 2.0690 (17) | C28—H28A | 0.9700 |
Cu2—O35 | 2.4221 (19) | C28—H28B | 0.9700 |
Cu2—O53 | 2.5994 (19) | C32—H32A | 0.9600 |
N21—C22 | 1.330 (3) | C32—H32B | 0.9600 |
N21—C25 | 1.391 (3) | C32—H32C | 0.9600 |
C22—N23 | 1.355 (3) | C33—H33A | 0.9700 |
C22—C32 | 1.484 (3) | C33—H33B | 0.9700 |
N23—C24 | 1.395 (3) | O34—H34A | 0.84 (1) |
C24—C25 | 1.359 (3) | O34—H34B | 0.84 (1) |
C24—C33 | 1.492 (3) | O35—H35A | 0.84 (3) |
C25—C26 | 1.490 (3) | O35—H35B | 0.84 (3) |
C26—N27 | 1.492 (3) | O61—H61A | 0.84 (3) |
N27—C28 | 1.480 (3) | O61—H61B | 0.85 (3) |
N27—C33ii | 1.514 (3) | O62—H62A | 0.84 (1) |
C28—C29 | 1.527 (3) | O62—H62B | 0.84 (1) |
C29—O31 | 1.234 (3) | O63—H63A | 0.84 (1) |
C29—O30 | 1.281 (3) | O63—H63B | 0.84 (3) |
O10—Cu1—O14 | 91.21 (7) | N27—C28—C29 | 109.37 (17) |
O10—Cu1—N1 | 166.48 (7) | O31—C29—O30 | 124.2 (2) |
O14—Cu1—N1 | 102.13 (7) | O31—C29—C28 | 119.3 (2) |
O10—Cu1—N7 | 82.87 (7) | O30—C29—C28 | 116.51 (19) |
O14—Cu1—N7 | 170.59 (7) | C29—O30—Cu2 | 114.94 (14) |
N1—Cu1—N7 | 84.17 (7) | C24—C33—N27ii | 115.46 (17) |
O10—Cu1—O15 | 91.86 (7) | O41—N41—O42 | 120.3 (2) |
O14—Cu1—O15 | 86.02 (7) | O41—N41—O43 | 120.8 (2) |
N1—Cu1—O15 | 91.24 (7) | O42—N41—O43 | 118.9 (2) |
N7—Cu1—O15 | 86.87 (7) | N41—O43—Cu1 | 122.73 (16) |
O10—Cu1—O43 | 84.37 (7) | O51—N51—O52 | 120.4 (2) |
O14—Cu1—O43 | 84.84 (7) | O51—N51—O53 | 120.0 (2) |
N1—Cu1—O43 | 94.57 (7) | O52—N51—O53 | 119.5 (2) |
N7—Cu1—O43 | 101.77 (7) | N51—O53—Cu2 | 120.63 (15) |
O15—Cu1—O43 | 170.03 (6) | C2—N3—H3A | 125.6 |
C2—N1—C5 | 106.92 (17) | C4—N3—H3A | 125.6 |
C2—N1—Cu1 | 139.08 (15) | C5—C6—H6A | 110.6 |
C5—N1—Cu1 | 109.98 (13) | N7—C6—H6A | 110.6 |
N1—C2—N3 | 109.50 (18) | C5—C6—H6B | 110.6 |
N1—C2—C12 | 126.2 (2) | N7—C6—H6B | 110.6 |
N3—C2—C12 | 124.3 (2) | H6A—C6—H6B | 108.8 |
C2—N3—C4 | 108.79 (17) | N7—C8—H8A | 109.9 |
C5—C4—N3 | 105.16 (18) | C9—C8—H8A | 109.9 |
C5—C4—C13 | 128.95 (19) | N7—C8—H8B | 109.9 |
N3—C4—C13 | 125.51 (19) | C9—C8—H8B | 109.9 |
C4—C5—N1 | 109.61 (18) | H8A—C8—H8B | 108.3 |
C4—C5—C6 | 134.29 (19) | C2—C12—H12A | 109.5 |
N1—C5—C6 | 116.00 (18) | C2—C12—H12B | 109.5 |
C5—C6—N7 | 105.46 (16) | H12A—C12—H12B | 109.5 |
C8—N7—C6 | 114.66 (17) | C2—C12—H12C | 109.5 |
C8—N7—C13i | 111.73 (17) | H12A—C12—H12C | 109.5 |
C6—N7—C13i | 112.48 (16) | H12B—C12—H12C | 109.5 |
C8—N7—Cu1 | 102.92 (12) | C4—C13—H13A | 108.8 |
C6—N7—Cu1 | 102.80 (12) | N7i—C13—H13A | 108.8 |
C13i—N7—Cu1 | 111.46 (13) | C4—C13—H13B | 108.8 |
N7—C8—C9 | 108.93 (17) | N7i—C13—H13B | 108.8 |
O11—C9—O10 | 124.0 (2) | H13A—C13—H13B | 107.7 |
O11—C9—C8 | 120.1 (2) | Cu1—O14—H14A | 115.2 (19) |
O10—C9—C8 | 115.84 (19) | Cu1—O14—H14B | 111 (2) |
C9—O10—Cu1 | 114.73 (14) | H14A—O14—H14B | 105 (2) |
C4—C13—N7i | 113.84 (18) | Cu1—O15—H15A | 98 (2) |
O30—Cu2—O34 | 94.11 (7) | Cu1—O15—H15B | 102 (2) |
O30—Cu2—N21 | 166.65 (7) | H15A—O15—H15B | 105 (2) |
O34—Cu2—N21 | 99.21 (7) | C22—N23—H23A | 125.6 |
O30—Cu2—N27 | 82.21 (7) | C24—N23—H23A | 125.6 |
O34—Cu2—N27 | 174.38 (7) | C25—C26—H26A | 110.6 |
N21—Cu2—N27 | 84.44 (7) | N27—C26—H26A | 110.6 |
O30—Cu2—O35 | 84.72 (7) | C25—C26—H26B | 110.6 |
O34—Cu2—O35 | 92.25 (7) | N27—C26—H26B | 110.6 |
N21—Cu2—O35 | 95.62 (7) | H26A—C26—H26B | 108.8 |
N27—Cu2—O35 | 91.64 (7) | N27—C28—H28A | 109.8 |
O30—Cu2—O53 | 85.36 (6) | C29—C28—H28A | 109.8 |
O34—Cu2—O53 | 76.31 (7) | N27—C28—H28B | 109.8 |
N21—Cu2—O53 | 96.84 (7) | C29—C28—H28B | 109.8 |
N27—Cu2—O53 | 99.08 (6) | H28A—C28—H28B | 108.2 |
O35—Cu2—O53 | 164.27 (6) | C22—C32—H32A | 109.5 |
C22—N21—C25 | 106.61 (17) | C22—C32—H32B | 109.5 |
C22—N21—Cu2 | 137.21 (15) | H32A—C32—H32B | 109.5 |
C25—N21—Cu2 | 109.28 (13) | C22—C32—H32C | 109.5 |
N21—C22—N23 | 109.61 (19) | H32A—C32—H32C | 109.5 |
N21—C22—C32 | 126.3 (2) | H32B—C32—H32C | 109.5 |
N23—C22—C32 | 124.1 (2) | C24—C33—H33A | 108.4 |
C22—N23—C24 | 108.84 (18) | N27ii—C33—H33A | 108.4 |
C25—C24—N23 | 104.89 (18) | C24—C33—H33B | 108.4 |
C25—C24—C33 | 128.23 (19) | N27ii—C33—H33B | 108.4 |
N23—C24—C33 | 126.66 (19) | H33A—C33—H33B | 107.5 |
C24—C25—N21 | 110.02 (18) | Cu2—O34—H34A | 117 (2) |
C24—C25—C26 | 134.12 (19) | Cu2—O34—H34B | 117 (2) |
N21—C25—C26 | 115.81 (17) | H34A—O34—H34B | 109 (2) |
C25—C26—N27 | 105.47 (16) | Cu2—O35—H35A | 110 (2) |
C28—N27—C26 | 114.94 (16) | Cu2—O35—H35B | 121 (2) |
C28—N27—C33ii | 111.27 (17) | H35A—O35—H35B | 105 (2) |
C26—N27—C33ii | 112.37 (15) | H61A—O61—H61B | 106 (2) |
C28—N27—Cu2 | 104.14 (12) | H62A—O62—H62B | 103 (2) |
C26—N27—Cu2 | 103.68 (12) | H63A—O63—H63B | 108 (2) |
C33ii—N27—Cu2 | 109.74 (12) | ||
O10—Cu1—N1—C2 | −126.5 (3) | N27—Cu2—N21—C25 | 4.30 (14) |
O14—Cu1—N1—C2 | 44.1 (2) | O35—Cu2—N21—C25 | −86.81 (14) |
N7—Cu1—N1—C2 | −143.0 (2) | O53—Cu2—N21—C25 | 102.81 (14) |
O15—Cu1—N1—C2 | 130.3 (2) | C25—N21—C22—N23 | −0.5 (2) |
O43—Cu1—N1—C2 | −41.6 (2) | Cu2—N21—C22—N23 | 145.56 (18) |
O10—Cu1—N1—C5 | 26.7 (4) | C25—N21—C22—C32 | 176.9 (2) |
O14—Cu1—N1—C5 | −162.71 (14) | Cu2—N21—C22—C32 | −37.1 (4) |
N7—Cu1—N1—C5 | 10.21 (14) | N21—C22—N23—C24 | −0.5 (3) |
O15—Cu1—N1—C5 | −76.52 (14) | C32—C22—N23—C24 | −178.0 (2) |
O43—Cu1—N1—C5 | 111.60 (14) | C22—N23—C24—C25 | 1.3 (2) |
C5—N1—C2—N3 | −0.7 (2) | C22—N23—C24—C33 | −173.7 (2) |
Cu1—N1—C2—N3 | 152.96 (18) | N23—C24—C25—N21 | −1.6 (2) |
C5—N1—C2—C12 | 179.5 (2) | C33—C24—C25—N21 | 173.3 (2) |
Cu1—N1—C2—C12 | −26.8 (4) | N23—C24—C25—C26 | −179.1 (2) |
N1—C2—N3—C4 | −0.2 (3) | C33—C24—C25—C26 | −4.2 (4) |
C12—C2—N3—C4 | 179.6 (2) | C22—N21—C25—C24 | 1.3 (2) |
C2—N3—C4—C5 | 1.1 (2) | Cu2—N21—C25—C24 | −154.94 (15) |
C2—N3—C4—C13 | −172.3 (2) | C22—N21—C25—C26 | 179.31 (18) |
N3—C4—C5—N1 | −1.5 (2) | Cu2—N21—C25—C26 | 23.0 (2) |
C13—C4—C5—N1 | 171.5 (2) | C24—C25—C26—N27 | 129.3 (2) |
N3—C4—C5—C6 | −177.7 (2) | N21—C25—C26—N27 | −48.0 (2) |
C13—C4—C5—C6 | −4.7 (4) | C25—C26—N27—C28 | 158.64 (17) |
C2—N1—C5—C4 | 1.4 (2) | C25—C26—N27—C33ii | −72.8 (2) |
Cu1—N1—C5—C4 | −160.57 (15) | C25—C26—N27—Cu2 | 45.67 (16) |
C2—N1—C5—C6 | 178.42 (19) | O30—Cu2—N27—C28 | 30.55 (13) |
Cu1—N1—C5—C6 | 16.4 (2) | N21—Cu2—N27—C28 | −149.39 (14) |
C4—C5—C6—N7 | 131.6 (3) | O35—Cu2—N27—C28 | −53.90 (13) |
N1—C5—C6—N7 | −44.5 (2) | O53—Cu2—N27—C28 | 114.55 (13) |
C5—C6—N7—C8 | 158.05 (17) | O30—Cu2—N27—C26 | 151.13 (12) |
C5—C6—N7—C13i | −72.8 (2) | N21—Cu2—N27—C26 | −28.80 (12) |
C5—C6—N7—Cu1 | 47.16 (17) | O35—Cu2—N27—C26 | 66.69 (12) |
O10—Cu1—N7—C8 | 31.67 (14) | O53—Cu2—N27—C26 | −124.87 (12) |
N1—Cu1—N7—C8 | −152.16 (14) | O30—Cu2—N27—C33ii | −88.64 (13) |
O15—Cu1—N7—C8 | −60.59 (13) | N21—Cu2—N27—C33ii | 91.42 (13) |
O43—Cu1—N7—C8 | 114.37 (13) | O35—Cu2—N27—C33ii | −173.09 (12) |
O10—Cu1—N7—C6 | 151.08 (13) | O53—Cu2—N27—C33ii | −4.64 (13) |
N1—Cu1—N7—C6 | −32.75 (13) | C26—N27—C28—C29 | −148.41 (18) |
O15—Cu1—N7—C6 | 58.82 (12) | C33ii—N27—C28—C29 | 82.4 (2) |
O43—Cu1—N7—C6 | −126.22 (12) | Cu2—N27—C28—C29 | −35.70 (19) |
O10—Cu1—N7—C13i | −88.21 (13) | N27—C28—C29—O31 | −158.3 (2) |
N1—Cu1—N7—C13i | 87.95 (13) | N27—C28—C29—O30 | 23.4 (3) |
O15—Cu1—N7—C13i | 179.52 (13) | O31—C29—O30—Cu2 | −174.47 (19) |
O43—Cu1—N7—C13i | −5.51 (14) | C28—C29—O30—Cu2 | 3.7 (2) |
C6—N7—C8—C9 | −149.67 (18) | O34—Cu2—O30—C29 | 164.11 (16) |
C13i—N7—C8—C9 | 80.8 (2) | N21—Cu2—O30—C29 | −19.9 (4) |
Cu1—N7—C8—C9 | −38.8 (2) | N27—Cu2—O30—C29 | −20.16 (15) |
N7—C8—C9—O11 | −152.6 (2) | O35—Cu2—O30—C29 | 72.23 (16) |
N7—C8—C9—O10 | 28.6 (3) | O53—Cu2—O30—C29 | −120.00 (16) |
O11—C9—O10—Cu1 | −179.2 (2) | C25—C24—C33—N27ii | −101.2 (3) |
C8—C9—O10—Cu1 | −0.5 (3) | N23—C24—C33—N27ii | 72.7 (3) |
O14—Cu1—O10—C9 | 154.16 (17) | O41—N41—O43—Cu1 | −56.3 (3) |
N1—Cu1—O10—C9 | −35.0 (4) | O42—N41—O43—Cu1 | 123.81 (19) |
N7—Cu1—O10—C9 | −18.51 (16) | O10—Cu1—O43—N41 | 167.17 (19) |
O15—Cu1—O10—C9 | 68.10 (17) | O14—Cu1—O43—N41 | −101.09 (19) |
O43—Cu1—O10—C9 | −121.15 (17) | N1—Cu1—O43—N41 | 0.70 (19) |
C5—C4—C13—N7i | −99.9 (3) | N7—Cu1—O43—N41 | 85.68 (19) |
N3—C4—C13—N7i | 71.9 (3) | O51—N51—O53—Cu2 | −49.7 (3) |
O30—Cu2—N21—C22 | −141.4 (3) | O52—N51—O53—Cu2 | 129.25 (19) |
O34—Cu2—N21—C22 | 34.5 (2) | O30—Cu2—O53—N51 | 179.93 (17) |
N27—Cu2—N21—C22 | −141.1 (2) | O34—Cu2—O53—N51 | −84.69 (17) |
O35—Cu2—N21—C22 | 127.8 (2) | N21—Cu2—O53—N51 | 13.17 (18) |
O53—Cu2—N21—C22 | −42.6 (2) | N27—Cu2—O53—N51 | 98.60 (17) |
O30—Cu2—N21—C25 | 4.0 (4) | O35—Cu2—O53—N51 | −129.0 (2) |
O34—Cu2—N21—C25 | 179.99 (14) |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O42iii | 0.86 | 2.00 | 2.853 (3) | 173 |
N23—H23A···O52iv | 0.86 | 2.07 | 2.927 (3) | 173 |
O14—H14A···O61v | 0.84 (1) | 1.81 (1) | 2.613 (3) | 158 (3) |
O14—H14B···O30 | 0.85 (1) | 1.94 (1) | 2.782 (2) | 178 (3) |
O15—H15A···O31 | 0.84 (1) | 1.89 (1) | 2.701 (2) | 160 (3) |
O15—H15B···O63v | 0.84 (1) | 1.98 (2) | 2.769 (3) | 155 (3) |
O34—H34A···O62 | 0.84 (1) | 1.98 (1) | 2.819 (3) | 174 (3) |
O34—H34B···O63 | 0.84 (1) | 1.86 (1) | 2.665 (3) | 160 (3) |
O35—H35A···O10 | 0.84 (3) | 2.02 (3) | 2.855 (2) | 174 (3) |
O35—H35B···O15vi | 0.84 (3) | 2.11 (3) | 2.938 (3) | 166 (3) |
O61—H61A···O11vii | 0.84 (3) | 1.98 (2) | 2.787 (3) | 161 (4) |
O61—H61B···O62vi | 0.85 (3) | 2.22 (4) | 2.770 (3) | 123 (4) |
O62—H62A···O31vii | 0.84 (1) | 1.94 (1) | 2.777 (3) | 173 (4) |
O62—H62B···O52 | 0.84 (1) | 2.24 (2) | 3.023 (3) | 154 (3) |
O63—H63A···O11vii | 0.84 (1) | 1.93 (1) | 2.751 (3) | 167 (3) |
O63—H63B···O43 | 0.84 (3) | 2.07 (3) | 2.898 (3) | 170 (3) |
O63—H63B···O42 | 0.84 (3) | 2.49 (2) | 3.120 (3) | 133 (3) |
Symmetry codes: (iii) −x, −y+1, −z+1; (iv) −x+1, −y+1, −z; (v) x−1, y, z; (vi) x+1, y, z; (vii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Cu2(C16H20N6O4)(NO3)2(H2O)4]·3H2O |
Mr | 737.59 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 7.7983 (9), 8.7523 (11), 22.509 (2) |
α, β, γ (°) | 91.802 (10), 93.479 (9), 114.023 (11) |
V (Å3) | 1398.0 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.61 |
Crystal size (mm) | 0.24 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker P4 diffractometer |
Absorption correction | ψ scan (XSCANS; Siemens, 1996) |
Tmin, Tmax | 0.638, 0.750 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12145, 6396, 5139 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.082, 1.02 |
No. of reflections | 6396 |
No. of parameters | 433 |
No. of restraints | 22 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.50, −0.48 |
Computer programs: XSCANS (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).
Cu1—O10 | 1.9484 (16) | Cu2—O30 | 1.9632 (15) |
Cu1—O14 | 1.9533 (16) | Cu2—O34 | 1.9697 (17) |
Cu1—N1 | 1.9789 (18) | Cu2—N21 | 1.9903 (18) |
Cu1—N7 | 2.0619 (17) | Cu2—N27 | 2.0690 (17) |
Cu1—O15 | 2.601 (2) | Cu2—O35 | 2.4221 (19) |
Cu1—O43 | 2.607 (2) | Cu2—O53 | 2.5994 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O42i | 0.86 | 2.00 | 2.853 (3) | 172.8 |
N23—H23A···O52ii | 0.86 | 2.07 | 2.927 (3) | 172.6 |
O14—H14A···O61iii | 0.84 (1) | 1.81 (1) | 2.613 (3) | 158 (3) |
O14—H14B···O30 | 0.85 (1) | 1.94 (1) | 2.782 (2) | 178 (3) |
O15—H15A···O31 | 0.84 (1) | 1.89 (1) | 2.701 (2) | 160 (3) |
O15—H15B···O63iii | 0.84 (1) | 1.98 (2) | 2.769 (3) | 155 (3) |
O34—H34A···O62 | 0.84 (1) | 1.98 (1) | 2.819 (3) | 174 (3) |
O34—H34B···O63 | 0.84 (1) | 1.86 (1) | 2.665 (3) | 160 (3) |
O35—H35A···O10 | 0.84 (3) | 2.02 (3) | 2.855 (2) | 174 (3) |
O35—H35B···O15iv | 0.84 (3) | 2.11 (3) | 2.938 (3) | 166 (3) |
O61—H61A···O11v | 0.84 (3) | 1.98 (2) | 2.787 (3) | 161 (4) |
O61—H61B···O62iv | 0.85 (3) | 2.22 (4) | 2.770 (3) | 123 (4) |
O62—H62A···O31v | 0.84 (1) | 1.94 (1) | 2.777 (3) | 173 (4) |
O62—H62B···O52 | 0.84 (1) | 2.24 (2) | 3.023 (3) | 154 (3) |
O63—H63A···O11v | 0.84 (1) | 1.93 (1) | 2.751 (3) | 167 (3) |
O63—H63B···O43 | 0.84 (3) | 2.07 (3) | 2.898 (3) | 170 (3) |
O63—H63B···O42 | 0.84 (3) | 2.49 (2) | 3.120 (3) | 133 (3) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) x−1, y, z; (iv) x+1, y, z; (v) x, y−1, z. |
Acknowledgements
SB thanks Universidad de Puebla, Mexico, for diffractometer time.
References
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Sosa, A. M., Ugalde-Saldívar, V. M., González, I. & Gasque, L. (2005). J. Electroanal. Chem. 579, 103–111. Web of Science CrossRef CAS Google Scholar
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Several dinucleating ligands containing imidazole and amines condensed via the Mannich reaction have been recently described, as well as their dicopper complexes (Driessen et al., 2005; Gasque et al., 2005; Mendoza-Díaz et al., 2002; Sosa et al., 2005), which exhibit interesting magnetic properties and a significant catecholase activity (Gasque et al., 2008). The complex presented here is an analogue of the first dicopper complex of this family reported (Mendoza-Díaz et al., 2002), in which perchlorate ion has been substituted by nitrate. As nitrate ions have a stronger ability to coordinate metal ions, the present complex is found to have six-coordinated CuII centers, while perchlorate ions afforded a cationic complex including five-coordinated metal centers.
The asymmetric unit of the title compound is formed by two half-complexes, placed close to inversion centers, and three lattice water molecules, lying on general positions. The triclinic unit cell thus contains two dinuclar centrosymmetric complexes (Figs. 1 and 2), which have similar structures. The bis(aminoimidazole) ligand coordinates two CuII atoms, via imidazole and tertiary N atoms, and one carboxylate O atom. Each CuII atom completes its coordination environment with two water molecules and one monodentate nitrate ion. The resulting coordination geometry is octahedral, with a very strong distortion due to the Jahn-Teller effect: Cu—O axial bond lengths are in the range of 2.4221 (19)–2.607 (2) Å, while the longest equatorial bond measures 2.0690 (17) Å (Table 1). The central 1,6-diazecine 10-membered ring displays a chair conformation, with a total puckering amplitude of 1.441 (2) and 1.434 (2) Å for Cu1- and Cu2-complex, respectively. The Cu···Cu separations, 7.3580 (9) and 7.3341 (9) Å, are probably compatible with a catecholase activity for this molecular compound (Gasque et al., 2008).
Lattice water molecules are active into forming a number of rather strong hydrogen bonds (Table 2), connecting neighboring molecules in the crystal. Strongest hydrogen bonds involve all water molecules, as both donor and acceptor, and carboxylate O atoms as acceptor groups (Fig. 3).