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Acta Cryst. (2007). E63, m1942    [ doi:10.1107/S1600536807028668 ]

Diamminebis[5-(pyrimidin-2-yl-[kappa]N1)tetrazolato-[kappa]N1]copper(II) dihydrate

J.-T. Liu and S.-D. Fan

Abstract top

The title compound, [Cu(C5H3N6)2(NH3)2]·2H2O, consists of a mononuclear copper complex and two solvent water molecules. The center CuII ion is coordinated by two NH3 and two 5-(pyrimidin-2-yl)tetrazolato ligands through the tetrazole N atoms in the 1 positions to form a square geometry. The two axial positions are occupied by weakly coordinated pyrimidinyl N atoms, thus giving rise to a highly distorted octahedral geometry. Furthermore, extensive intermolecular hydrogen-bond interactions lead to the formation of a three-dimensional network.

Comment top

The crystal structures of Fe(II) and Co(II) complexes with 5-(pyrimidin-2-yl)tetrazolate ligand have been reported recently (Rodríguez et al., 2005), which feature a two-dimensional square-grid-like network. And, the ligands coordinate to metal atoms through one of the pyrimidinyl nitrogen atoms and the 1- and 3-positon tetrazole nitrogen atoms. The title complex, diamminobis[5-(pyrimidin-2-yl-κN1)tetrazolato-κN1]copper(II) dehydrate (I) performs a mono-nuclear structure (Fig. 1), in which the center CuII atom, located on a normal position, is normally coordinated by two NH3 and two ligand molecules using tetrazole N atoms in 1-position to form a square geometry. Simultaneously, two apical positions in CuII atom form weak coordination (Cu1—N11 = 2.429 (2) and Cu1—N5 = 2.728 (2) Å) with two pyrimidinyl N atoms of two ligands, thus giving a highly distorted octahedral geometry (see Table 1). In addition, a three-dimensional supramolecular framework (Fig. 2) is formed by the intermolecular extensive N—H···O, N—H···N, O—H···N and O—H···O hydrogen-bond interactions between parking water molecules and complex molecules. The hydrogen bond parameters are listed in Table 2.

Related literature top

For related literature, see: Demko & Sharpless (2001); Rodríguez et al. (2005).

Experimental top

TThe ligand, 2-(1H-tetrazol-5-yl)pyrimidine (L) was synthesized according to the literature method (Demko & Sharpless, 2001). CuCl2·2H2O (34 mg, 0.2 mmol) and L (60 mg, 0.4 mmol) were dissolved in ammonium hydroxide (20%, 10 ml). The solution was filtered, and then filtrate was allowed to stand for about 10 days. Blue crystals of (I) were isolated in about 30% yield.

Refinement top

H atoms bound to carbon and amine were included in calculated positions and treated in the subsequent refinement as riding atoms, with C—H = 0.93 and N—H = 0.89 Å and Uiso(H) = 1.2 and 1.5 Ueq(C and N), respectively. The H atoms of the water molecules were located in Fourier difference maps and refined with isotropic displacement parameters set at 1.5 times those of the parent O atoms.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Three-dimensional hydrogen-bonded network.
Diamminebis[5-(pyrimidin-2-yl-κN1)tetrazolato-κN1]copper(II) dihydrate top
Crystal data top
[Cu(C5H3N6)2(NH3)2]·2H2OZ = 2
Mr = 427.91F000 = 438
Triclinic, P1Dx = 1.605 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 7.1533 (12) ÅCell parameters from 3035 reflections
b = 9.5708 (16) Åθ = 2.5–26.4º
c = 13.155 (2) ŵ = 1.28 mm−1
α = 97.048 (3)ºT = 294 (2) K
β = 90.214 (2)ºBlock, blue
γ = 97.777 (3)º0.22 × 0.22 × 0.20 mm
V = 885.4 (2) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer		3549 independent reflections
Radiation source: fine-focus sealed tube3104 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.023
T = 294(2) Kθmax = 26.4º
φ and ω scansθmin = 1.6º
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		h = −6→8
Tmin = 0.975, Tmax = 1.000k = −11→10
5086 measured reflectionsl = −16→16
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.097  w = 1/[σ2(Fo2) + (0.0583P)2 + 0.2049P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3549 reflectionsΔρmax = 0.56 e Å−3
257 parametersΔρmin = −0.63 e Å−3
4 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.096 (5)
Crystal data top
[Cu(C5H3N6)2(NH3)2]·2H2Oγ = 97.777 (3)º
Mr = 427.91V = 885.4 (2) Å3
Triclinic, P1Z = 2
a = 7.1533 (12) ÅMo Kα
b = 9.5708 (16) ŵ = 1.28 mm−1
c = 13.155 (2) ÅT = 294 (2) K
α = 97.048 (3)º0.22 × 0.22 × 0.20 mm
β = 90.214 (2)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		3549 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		3104 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 1.000Rint = 0.023
5086 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0364 restraints
wR(F2) = 0.097H atoms treated by a mixture of
independent and constrained refinement
S = 1.04Δρmax = 0.56 e Å−3
3549 reflectionsΔρmin = −0.63 e Å−3
257 parameters
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
Cu10.23179 (3)0.95624 (3)0.245828 (19)0.02515 (13)
N10.2492 (3)1.0675 (2)0.38683 (14)0.0257 (4)
N20.2601 (3)1.2084 (2)0.41174 (16)0.0352 (5)
N30.2667 (3)1.2353 (2)0.51209 (17)0.0402 (5)
N40.2606 (3)1.1139 (2)0.55440 (15)0.0333 (5)
N50.2149 (3)0.7757 (2)0.39173 (18)0.0384 (5)
N60.2597 (4)0.8204 (2)0.57417 (18)0.0448 (6)
N70.2131 (3)0.8657 (2)0.09642 (15)0.0285 (4)
N80.1767 (3)0.7331 (2)0.04961 (17)0.0389 (5)
N90.1783 (4)0.7390 (3)−0.05057 (18)0.0469 (6)
N100.2150 (3)0.8732 (3)−0.07049 (16)0.0410 (5)
N110.2867 (3)1.1532 (2)0.14470 (15)0.0314 (4)
N120.2938 (3)1.1822 (3)−0.03200 (16)0.0418 (5)
C10.2495 (3)1.0122 (2)0.47534 (17)0.0246 (5)
C20.2402 (3)0.8601 (2)0.48099 (18)0.0282 (5)
C30.2101 (5)0.6381 (3)0.3973 (3)0.0554 (8)
H3A0.19210.57510.33730.067*
C40.2309 (5)0.5847 (3)0.4888 (3)0.0641 (10)
H4A0.22870.48790.49160.077*
C50.2547 (5)0.6800 (3)0.5747 (3)0.0642 (10)
H5A0.26830.64610.63730.077*
C60.2364 (3)0.9490 (3)0.02177 (17)0.0284 (5)
C70.2752 (3)1.1045 (3)0.04536 (18)0.0291 (5)
C80.3217 (4)1.2939 (3)0.1692 (2)0.0407 (6)
H8A0.33231.33160.23790.049*
C90.3426 (4)1.3842 (3)0.0953 (2)0.0478 (7)
H9A0.36621.48220.11240.057*
C100.3270 (4)1.3236 (3)−0.0047 (2)0.0502 (7)
H10A0.33991.3827−0.05600.060*
N140.5061 (3)0.9386 (3)0.24816 (16)0.0369 (5)
H14A0.52540.86820.28350.055*
H14B0.57041.01960.27770.055*
H14C0.54490.92030.18430.055*
N13−0.0473 (3)0.9502 (3)0.24504 (15)0.0383 (5)
H13A−0.09860.88130.28010.057*
H13B−0.09150.93340.18070.057*
H13C−0.07681.03320.27390.057*
O1W0.6222 (4)0.6186 (4)0.2726 (2)0.0799 (8)
H2WA0.895 (7)0.449 (3)0.145 (4)0.120*
H1WA0.655 (7)0.643 (6)0.3348 (14)0.120*
O2W0.9450 (4)0.5292 (3)0.17569 (19)0.0651 (6)
H2WB1.008 (6)0.579 (4)0.135 (3)0.098*
H1WB0.731 (3)0.610 (6)0.251 (3)0.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.01906 (17)0.0352 (2)0.02059 (18)0.00532 (11)−0.00056 (10)−0.00088 (11)
N10.0269 (10)0.0287 (10)0.0217 (9)0.0063 (8)0.0015 (7)0.0010 (8)
N20.0455 (13)0.0277 (10)0.0331 (11)0.0075 (9)0.0035 (9)0.0042 (9)
N30.0575 (15)0.0301 (11)0.0322 (12)0.0083 (10)0.0039 (10)−0.0019 (9)
N40.0457 (12)0.0274 (10)0.0259 (10)0.0048 (9)0.0015 (9)0.0000 (8)
N50.0390 (12)0.0318 (11)0.0415 (13)0.0038 (9)0.0001 (10)−0.0051 (9)
N60.0580 (15)0.0366 (12)0.0408 (13)0.0028 (11)−0.0064 (11)0.0130 (10)
N70.0244 (10)0.0329 (10)0.0269 (10)0.0040 (8)−0.0010 (8)−0.0012 (8)
N80.0427 (13)0.0353 (12)0.0363 (12)0.0059 (10)−0.0024 (9)−0.0054 (9)
N90.0540 (15)0.0445 (14)0.0380 (13)0.0049 (11)−0.0038 (11)−0.0101 (10)
N100.0474 (13)0.0467 (14)0.0263 (11)0.0057 (11)−0.0018 (9)−0.0056 (10)
N110.0341 (11)0.0340 (11)0.0259 (10)0.0057 (9)0.0019 (8)0.0016 (8)
N120.0441 (13)0.0507 (14)0.0296 (11)−0.0030 (11)−0.0026 (9)0.0113 (10)
C10.0214 (10)0.0305 (12)0.0211 (11)0.0040 (9)0.0002 (8)0.0004 (9)
C20.0238 (11)0.0277 (12)0.0327 (12)0.0026 (9)0.0006 (9)0.0039 (10)
C30.0542 (19)0.0307 (15)0.076 (2)0.0039 (13)−0.0033 (16)−0.0113 (14)
C40.067 (2)0.0276 (15)0.099 (3)0.0053 (14)−0.006 (2)0.0125 (17)
C50.081 (2)0.0436 (18)0.074 (2)0.0062 (17)−0.0107 (19)0.0299 (17)
C60.0199 (10)0.0409 (13)0.0234 (11)0.0045 (9)−0.0001 (8)−0.0007 (9)
C70.0202 (11)0.0407 (13)0.0258 (12)0.0033 (9)0.0002 (9)0.0033 (10)
C80.0456 (15)0.0358 (14)0.0389 (14)0.0051 (11)0.0020 (12)−0.0015 (11)
C90.0487 (17)0.0344 (14)0.0589 (19)−0.0019 (12)0.0016 (14)0.0089 (13)
C100.0549 (18)0.0475 (17)0.0496 (17)−0.0036 (14)0.0000 (14)0.0239 (14)
N140.0262 (10)0.0590 (14)0.0258 (10)0.0120 (10)−0.0029 (8)0.0000 (9)
N130.0230 (10)0.0663 (15)0.0250 (10)0.0072 (10)−0.0001 (8)0.0023 (10)
O1W0.0835 (19)0.094 (2)0.0572 (16)0.0256 (17)−0.0117 (15)−0.0251 (15)
O2W0.0788 (18)0.0543 (14)0.0550 (14)0.0030 (12)0.0053 (12)−0.0155 (11)
Geometric parameters (Å, °) top
Cu1—N12.0170 (18)N12—C101.345 (4)
Cu1—N52.728 (2)C1—C21.459 (3)
Cu1—N72.0447 (19)C3—C41.379 (5)
Cu1—N112.429 (2)C3—H3A0.9300
Cu1—N131.990 (2)C4—C51.357 (5)
Cu1—N141.992 (2)C4—H4A0.9300
N1—C11.337 (3)C5—H5A0.9300
N1—N21.339 (3)C6—C71.471 (3)
N2—N31.313 (3)C8—C91.374 (4)
N3—N41.344 (3)C8—H8A0.9300
N4—C11.329 (3)C9—C101.369 (4)
N5—C31.324 (4)C9—H9A0.9300
N5—C21.338 (3)C10—H10A0.9300
N6—C21.339 (3)N14—H14A0.8900
N6—C51.341 (4)N14—H14B0.8900
N7—N81.332 (3)N14—H14C0.8900
N7—C61.336 (3)N13—H13A0.8900
N8—N91.326 (3)N13—H13B0.8900
N9—N101.334 (3)N13—H13C0.8900
N10—C61.332 (3)O1W—H1WA0.846 (10)
N11—C71.331 (3)O1W—H1WB0.843 (10)
N11—C81.334 (3)O2W—H2WA0.849 (10)
N12—C71.329 (3)O2W—H2WB0.848 (10)
N13—Cu1—N14173.45 (9)C4—C3—H3A118.8
N13—Cu1—N190.18 (8)C5—C4—C3117.0 (3)
N14—Cu1—N191.95 (8)C5—C4—H4A121.5
N13—Cu1—N788.98 (8)C3—C4—H4A121.5
N14—Cu1—N789.61 (8)N6—C5—C4123.4 (3)
N1—Cu1—N7173.28 (7)N6—C5—H5A118.3
N13—Cu1—N1194.55 (8)C4—C5—H5A118.3
N14—Cu1—N1191.24 (8)N10—C6—N7111.5 (2)
N1—Cu1—N1198.88 (7)N10—C6—C7127.4 (2)
N7—Cu1—N1174.54 (7)N7—C6—C7121.1 (2)
C1—N1—N2106.16 (18)N12—C7—N11126.4 (2)
C1—N1—Cu1125.67 (16)N12—C7—C6118.5 (2)
N2—N1—Cu1128.17 (15)N11—C7—C6115.1 (2)
N3—N2—N1107.98 (19)N11—C8—C9121.5 (3)
N2—N3—N4110.3 (2)N11—C8—H8A119.2
C1—N4—N3104.76 (19)C9—C8—H8A119.2
C3—N5—C2115.6 (3)C10—C9—C8117.1 (3)
C2—N6—C5114.4 (3)C10—C9—H9A121.5
N8—N7—C6105.87 (19)C8—C9—H9A121.5
N8—N7—Cu1134.76 (17)N12—C10—C9122.9 (3)
C6—N7—Cu1119.35 (16)N12—C10—H10A118.6
N9—N8—N7107.8 (2)C9—C10—H10A118.6
N8—N9—N10110.8 (2)Cu1—N14—H14A109.5
C6—N10—N9104.1 (2)Cu1—N14—H14B109.5
C7—N11—C8116.9 (2)H14A—N14—H14B109.5
C7—N11—Cu1109.90 (16)Cu1—N14—H14C109.5
C8—N11—Cu1133.21 (17)H14A—N14—H14C109.5
C7—N12—C10115.2 (2)H14B—N14—H14C109.5
N4—C1—N1110.8 (2)Cu1—N13—H13A109.5
N4—C1—C2126.1 (2)Cu1—N13—H13B109.5
N1—C1—C2123.1 (2)H13A—N13—H13B109.5
N5—C2—N6127.2 (2)Cu1—N13—H13C109.5
N5—C2—C1116.0 (2)H13A—N13—H13C109.5
N6—C2—C1116.8 (2)H13B—N13—H13C109.5
N5—C3—C4122.4 (3)H1WA—O1W—H1WB96 (5)
N5—C3—H3A118.8H2WA—O2W—H2WB112 (5)
N13—Cu1—N1—C192.85 (19)C3—N5—C2—N6−0.5 (4)
N14—Cu1—N1—C1−80.95 (19)C3—N5—C2—C1178.8 (2)
N11—Cu1—N1—C1−172.51 (18)C5—N6—C2—N50.8 (4)
N13—Cu1—N1—N2−86.2 (2)C5—N6—C2—C1−178.4 (3)
N14—Cu1—N1—N2100.0 (2)N4—C1—C2—N5175.0 (2)
N11—Cu1—N1—N28.5 (2)N1—C1—C2—N5−5.5 (3)
C1—N1—N2—N30.0 (3)N4—C1—C2—N6−5.7 (4)
Cu1—N1—N2—N3179.19 (16)N1—C1—C2—N6173.8 (2)
N1—N2—N3—N40.1 (3)C2—N5—C3—C4−0.4 (5)
N2—N3—N4—C1−0.2 (3)N5—C3—C4—C50.7 (5)
N13—Cu1—N7—N8−83.5 (2)C2—N6—C5—C4−0.4 (5)
N14—Cu1—N7—N890.1 (2)C3—C4—C5—N6−0.3 (6)
N11—Cu1—N7—N8−178.6 (2)N9—N10—C6—N7−0.3 (3)
N14—Cu1—N7—C6−91.74 (18)N9—N10—C6—C7−178.6 (2)
N11—Cu1—N7—C6−0.35 (16)N8—N7—C6—N100.3 (3)
C6—N7—N8—N9−0.1 (3)Cu1—N7—C6—N10−178.39 (16)
Cu1—N7—N8—N9178.26 (17)N8—N7—C6—C7178.7 (2)
N7—N8—N9—N10−0.1 (3)Cu1—N7—C6—C70.0 (3)
N8—N9—N10—C60.3 (3)C10—N12—C7—N11−0.2 (4)
N13—Cu1—N11—C7−86.98 (16)C10—N12—C7—C6179.3 (2)
N14—Cu1—N11—C789.95 (16)C8—N11—C7—N12−0.5 (4)
N1—Cu1—N11—C7−177.88 (15)Cu1—N11—C7—N12178.6 (2)
N7—Cu1—N11—C70.69 (15)C8—N11—C7—C6180.0 (2)
N13—Cu1—N11—C891.9 (2)Cu1—N11—C7—C6−0.9 (2)
N14—Cu1—N11—C8−91.1 (2)N10—C6—C7—N12−0.7 (4)
N1—Cu1—N11—C81.0 (2)N7—C6—C7—N12−178.8 (2)
N7—Cu1—N11—C8179.6 (3)N10—C6—C7—N11178.8 (2)
N3—N4—C1—N10.2 (3)N7—C6—C7—N110.7 (3)
N3—N4—C1—C2179.8 (2)C7—N11—C8—C90.8 (4)
N2—N1—C1—N4−0.2 (3)Cu1—N11—C8—C9−178.1 (2)
Cu1—N1—C1—N4−179.34 (15)N11—C8—C9—C10−0.4 (4)
N2—N1—C1—C2−179.7 (2)C7—N12—C10—C90.6 (4)
Cu1—N1—C1—C21.1 (3)C8—C9—C10—N12−0.4 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N14—H14A···O1W0.892.563.332 (4)145
N14—H14A···N4i0.892.593.209 (3)127
N14—H14B···N6i0.892.523.345 (3)154
N14—H14C···N12ii0.892.483.339 (3)162
N13—H13A···N4iii0.892.473.137 (3)132
N13—H13B···N12iv0.892.483.325 (3)158
O2W—H2WA···N9v0.85 (1)2.07 (2)2.901 (3)168 (5)
O1W—H1WA···N3i0.85 (1)2.23 (2)3.053 (3)165 (5)
O1W—H1WA···N4i0.85 (1)2.59 (4)3.227 (3)133 (5)
O2W—H2WB···N8vi0.85 (1)2.199 (12)3.041 (4)172 (4)
O1W—H1WB···O2W0.84 (1)2.01 (2)2.825 (4)161 (5)
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+2, −z; (iii) −x, −y+2, −z+1; (iv) −x, −y+2, −z; (v) −x+1, −y+1, −z; (vi) x+1, y, z.
Table 1
Selected geometric parameters (Å, °) top
Cu1—N12.0170 (18)Cu1—N112.429 (2)
Cu1—N52.728 (2)Cu1—N131.990 (2)
Cu1—N72.0447 (19)Cu1—N141.992 (2)
N13—Cu1—N14173.45 (9)N1—Cu1—N7173.28 (7)
N13—Cu1—N190.18 (8)N13—Cu1—N1194.55 (8)
N14—Cu1—N191.95 (8)N14—Cu1—N1191.24 (8)
N13—Cu1—N788.98 (8)N1—Cu1—N1198.88 (7)
N14—Cu1—N789.61 (8)N7—Cu1—N1174.54 (7)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N14—H14A···O1W0.892.563.332 (4)145
N14—H14A···N4i0.892.593.209 (3)127
N14—H14B···N6i0.892.523.345 (3)154
N14—H14C···N12ii0.892.483.339 (3)162
N13—H13A···N4iii0.892.473.137 (3)132
N13—H13B···N12iv0.892.483.325 (3)158
O2W—H2WA···N9v0.85 (1)2.07 (2)2.901 (3)168 (5)
O1W—H1WA···N3i0.85 (1)2.23 (2)3.053 (3)165 (5)
O1W—H1WA···N4i0.85 (1)2.59 (4)3.227 (3)133 (5)
O2W—H2WB···N8vi0.85 (1)2.199 (12)3.041 (4)172 (4)
O1W—H1WB···O2W0.84 (1)2.01 (2)2.825 (4)161 (5)
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+2, −z; (iii) −x, −y+2, −z+1; (iv) −x, −y+2, −z; (v) −x+1, −y+1, −z; (vi) x+1, y, z.
Acknowledgements top

The authors thank Dalian Nationalities University for supporting this work.

references
References top

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Rodríguez, A., Kivekäsb, R. & Colacio, E. (2005). Chem. Commun. pp. 5228–5230.

Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.