Bis(acetato-κO,O')bis-(3,5-dimethyl-1H-pyrazole-κN)copper(II).

In the title compound, [Cu(C(2)H(3)O(2))(2)(C(5)H(8)N(2))(2)], the Cu(II) atom has a distorted tetra-gonal-bipyramidal geometry, with the equatorial plane formed by two N atoms belonging to two 3,5-dimethyl-1H-pyrazole ligands and two O atoms from two acetate anions. The second O atoms of the acetate groups provide elongated Cu-O axial contacts, so that the acetates appear to be coordinated in a pseudo-chelate fashion. The pyrazole ligands are situated in cis positions with respect to each other. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming a one-dimensional chain.

Related literature

For properties and applications of 1H-pyrazole and its 3,5-substituted derivatives, see: Fritsky et al. (1993 ▶, 1994a ▶,b ▶); Halcrow (2001 ▶); Jain et al. (2004 ▶); Krämer (1999 ▶); Krämer et al. (2002 ▶); Raptis et al. (1999 ▶); Seredyuk et al. (2007 ▶); Skopenko et al. (1990 ▶). For related compounds, see: Barooah et al. (2006 ▶); Deka et al. (2006 ▶); Karmakar et al. (2007 ▶); Porai-Koshits (1980 ▶); Pradeep et al. (2006 ▶).

Experimental

Crystal data

[Cu(C2H3O2)2(C5H8N2)2]

M = 373.90

Triclinic,

a = 9.2861 (11) Å

b = 10.1684 (12) Å

c = 10.3139 (13) Å

α = 110.755 (9)°

β = 100.901 (10)°

γ = 99.383 (9)°

V = 865.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.29 mm−1

T = 133 K

0.50 × 0.08 × 0.07 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: numerical (X-RED; Stoe & Cie, 2002 ▶) T min = 0.790, T max = 0.935

7882 measured reflections

3713 independent reflections

3129 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.071

S = 1.02

3713 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.66 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019400/hy2196sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019400/hy2196Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C2H3O2)2(C5H8N2)2]	Z = 2
Mr = 373.90	F(000) = 390
Triclinic, P1	Dx = 1.434 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2861 (11) Å	Cell parameters from 7882 reflections
b = 10.1684 (12) Å	θ = 2.2–27.1°
c = 10.3139 (13) Å	µ = 1.29 mm−1
α = 110.755 (9)°	T = 133 K
β = 100.901 (10)°	Needle, blue
γ = 99.383 (9)°	0.50 × 0.08 × 0.07 mm
V = 865.7 (2) Å3

Stoe IPDSII diffractometer	3713 independent reflections
Radiation source: fine-focus sealed tube	3129 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω scans	θmax = 27.1°, θmin = 2.2°
Absorption correction: numerical (X-RED; Stoe & Cie, 2002)	h = −11→11
Tmin = 0.790, Tmax = 0.935	k = −12→12
7882 measured reflections	l = −13→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0405P)2] where P = (Fo2 + 2Fc2)/3
3713 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.66 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.59542 (3)	0.26364 (3)	0.28774 (3)	0.01892 (8)
N1	0.46111 (18)	0.31000 (19)	0.1448 (2)	0.0219 (4)
N2	0.35711 (19)	0.2059 (2)	0.0274 (2)	0.0236 (4)
N3	0.41420 (18)	0.17191 (19)	0.3311 (2)	0.0206 (4)
N4	0.30556 (18)	0.2416 (2)	0.3681 (2)	0.0208 (4)
O1	0.73397 (15)	0.25272 (16)	0.45427 (17)	0.0241 (3)
O2	0.69120 (17)	0.47040 (17)	0.52556 (18)	0.0290 (3)
O3	0.77354 (16)	0.32001 (17)	0.21787 (18)	0.0274 (3)
O4	0.67255 (17)	0.08587 (17)	0.09809 (18)	0.0313 (4)
C1	0.4435 (2)	0.4379 (2)	0.1444 (2)	0.0236 (4)
C2	0.3264 (2)	0.4129 (3)	0.0235 (3)	0.0281 (5)
H2A	0.2906	0.4827	−0.0025	0.080*
C3	0.2751 (2)	0.2644 (3)	−0.0486 (2)	0.0264 (5)
C4	0.5404 (3)	0.5761 (2)	0.2603 (3)	0.0295 (5)
H4A	0.4975	0.6013	0.3409	0.080*
H4B	0.5460	0.6519	0.2251	0.080*
H4C	0.6402	0.5645	0.2900	0.080*
C5	0.1575 (3)	0.1717 (3)	−0.1863 (3)	0.0361 (6)
H5A	0.2058	0.1261	−0.2587	0.080*
H5B	0.1002	0.2310	−0.2170	0.080*
H5C	0.0909	0.0986	−0.1719	0.080*
C6	0.3738 (2)	0.0426 (2)	0.3370 (2)	0.0223 (4)
C7	0.2394 (2)	0.0308 (2)	0.3797 (3)	0.0260 (5)
H7	0.1875	−0.0481	0.3924	0.080*
C8	0.1996 (2)	0.1597 (2)	0.3991 (2)	0.0226 (4)
C9	0.4646 (3)	−0.0668 (3)	0.2981 (3)	0.0331 (5)
H9A	0.4376	−0.1180	0.1954	0.080*
H9B	0.4442	−0.1345	0.3417	0.080*
H9C	0.5705	−0.0183	0.3320	0.080*
C10	0.0700 (2)	0.2149 (3)	0.4456 (3)	0.0317 (5)
H10A	0.1082	0.3080	0.5246	0.080*
H10B	0.0138	0.1479	0.4753	0.080*
H10C	0.0049	0.2240	0.3668	0.080*
C11	0.7570 (2)	0.3795 (2)	0.5494 (2)	0.0232 (4)
C12	0.8678 (3)	0.4198 (3)	0.6921 (3)	0.0344 (5)
H12A	0.9637	0.4742	0.6944	0.080*
H12B	0.8803	0.3331	0.7054	0.080*
H12C	0.8303	0.4777	0.7678	0.080*
C13	0.7706 (2)	0.1986 (3)	0.1243 (2)	0.0268 (5)
C14	0.8912 (3)	0.1923 (3)	0.0435 (3)	0.0450 (7)
H14A	0.9847	0.1944	0.1038	0.080*
H14B	0.9053	0.2743	0.0174	0.080*
H14C	0.8601	0.1042	−0.0418	0.080*
H4	0.319 (3)	0.334 (3)	0.384 (3)	0.023 (6)*
H2	0.351 (3)	0.118 (3)	0.003 (3)	0.027 (7)*

	U11	U22	U33	U12	U13	U23
Cu1	0.01590 (12)	0.01845 (13)	0.02150 (14)	0.00555 (9)	0.00670 (9)	0.00546 (10)
N1	0.0212 (8)	0.0212 (9)	0.0221 (10)	0.0048 (7)	0.0071 (7)	0.0068 (8)
N2	0.0227 (8)	0.0215 (10)	0.0224 (10)	0.0043 (7)	0.0060 (7)	0.0047 (8)
N3	0.0179 (7)	0.0201 (9)	0.0239 (10)	0.0087 (7)	0.0071 (7)	0.0064 (8)
N4	0.0182 (8)	0.0218 (9)	0.0241 (10)	0.0090 (7)	0.0086 (7)	0.0078 (8)
O1	0.0202 (7)	0.0217 (8)	0.0275 (9)	0.0083 (6)	0.0053 (6)	0.0057 (7)
O2	0.0331 (8)	0.0240 (8)	0.0318 (9)	0.0132 (7)	0.0121 (7)	0.0088 (7)
O3	0.0225 (7)	0.0264 (8)	0.0282 (9)	0.0029 (6)	0.0101 (6)	0.0046 (7)
O4	0.0274 (8)	0.0259 (8)	0.0331 (10)	0.0053 (7)	0.0110 (7)	0.0024 (7)
C1	0.0259 (10)	0.0257 (11)	0.0233 (12)	0.0093 (8)	0.0126 (9)	0.0102 (10)
C2	0.0303 (11)	0.0317 (12)	0.0293 (13)	0.0140 (9)	0.0125 (10)	0.0151 (11)
C3	0.0215 (9)	0.0365 (13)	0.0242 (12)	0.0094 (9)	0.0096 (9)	0.0126 (10)
C4	0.0364 (11)	0.0227 (11)	0.0294 (13)	0.0073 (9)	0.0106 (10)	0.0097 (10)
C5	0.0264 (11)	0.0475 (15)	0.0279 (13)	0.0065 (10)	0.0030 (10)	0.0109 (12)
C6	0.0225 (9)	0.0204 (10)	0.0233 (11)	0.0077 (8)	0.0063 (8)	0.0069 (9)
C7	0.0208 (9)	0.0273 (11)	0.0302 (12)	0.0035 (8)	0.0076 (9)	0.0123 (10)
C8	0.0175 (9)	0.0267 (11)	0.0214 (11)	0.0057 (8)	0.0054 (8)	0.0069 (9)
C9	0.0336 (11)	0.0251 (12)	0.0473 (16)	0.0153 (10)	0.0167 (11)	0.0155 (11)
C10	0.0225 (10)	0.0410 (14)	0.0336 (13)	0.0129 (10)	0.0137 (10)	0.0118 (12)
C11	0.0185 (9)	0.0244 (11)	0.0256 (12)	0.0059 (8)	0.0086 (8)	0.0073 (9)
C12	0.0298 (11)	0.0380 (14)	0.0276 (13)	0.0105 (10)	0.0049 (10)	0.0048 (11)
C13	0.0203 (9)	0.0308 (12)	0.0238 (12)	0.0061 (9)	0.0048 (9)	0.0053 (10)
C14	0.0316 (12)	0.0565 (18)	0.0360 (15)	0.0053 (12)	0.0197 (11)	0.0029 (14)

Cu1—N1	1.9851 (18)	C4—H4B	0.9600
Cu1—N3	1.9925 (16)	C4—H4C	0.9600
Cu1—O1	1.9909 (15)	C5—H5A	0.9600
Cu1—O2	2.4774 (18)	C5—H5B	0.9600
Cu1—O3	2.0045 (14)	C5—H5C	0.9600
Cu1—O4	2.4603 (16)	C6—C7	1.402 (3)
N1—C1	1.338 (3)	C6—C9	1.492 (3)
N1—N2	1.355 (3)	C7—C8	1.377 (3)
N2—C3	1.342 (3)	C7—H7	0.9300
N2—H2	0.82 (3)	C8—C10	1.497 (3)
N3—C6	1.333 (3)	C9—H9A	0.9600
N3—N4	1.361 (2)	C9—H9B	0.9600
N4—C8	1.343 (3)	C9—H9C	0.9600
N4—H4	0.87 (3)	C10—H10A	0.9600
O1—C11	1.266 (3)	C10—H10B	0.9600
O2—C11	1.256 (2)	C10—H10C	0.9600
O3—C13	1.262 (3)	C11—C12	1.502 (3)
O4—C13	1.250 (3)	C12—H12A	0.9600
C1—C2	1.405 (3)	C12—H12B	0.9600
C1—C4	1.485 (3)	C12—H12C	0.9600
C2—C3	1.377 (3)	C13—C14	1.513 (3)
C2—H2A	0.9300	C14—H14A	0.9600
C3—C5	1.492 (3)	C14—H14B	0.9600
C4—H4A	0.9600	C14—H14C	0.9600
N1—Cu1—O1	170.00 (7)	C3—C5—H5A	109.5
N1—Cu1—N3	89.80 (7)	C3—C5—H5B	109.5
O1—Cu1—N3	91.52 (7)	H5A—C5—H5B	109.5
N1—Cu1—O3	90.43 (7)	C3—C5—H5C	109.5
O1—Cu1—O3	90.04 (6)	H5A—C5—H5C	109.5
N3—Cu1—O3	169.70 (7)	H5B—C5—H5C	109.5
N1—Cu1—O4	91.91 (7)	N3—C6—C7	109.75 (17)
O1—Cu1—O4	96.79 (6)	N3—C6—C9	121.28 (18)
N3—Cu1—O4	111.84 (6)	C7—C6—C9	128.9 (2)
O3—Cu1—O4	57.86 (6)	C8—C7—C6	106.03 (18)
N1—Cu1—O2	112.23 (6)	C8—C7—H7	127.0
O1—Cu1—O2	57.78 (6)	C6—C7—H7	127.0
N3—Cu1—O2	95.42 (7)	N4—C8—C7	106.80 (17)
O3—Cu1—O2	94.03 (6)	N4—C8—C10	121.04 (19)
O4—Cu1—O2	143.81 (5)	C7—C8—C10	132.2 (2)
C1—N1—N2	106.62 (17)	C6—C9—H9A	109.5
C1—N1—Cu1	130.74 (16)	C6—C9—H9B	109.5
N2—N1—Cu1	122.49 (13)	H9A—C9—H9B	109.5
C3—N2—N1	111.34 (19)	C6—C9—H9C	109.5
C3—N2—H2	125.2 (19)	H9A—C9—H9C	109.5
N1—N2—H2	123.2 (18)	H9B—C9—H9C	109.5
C6—N3—N4	106.06 (15)	C8—C10—H10A	109.5
C6—N3—Cu1	131.10 (13)	C8—C10—H10B	109.5
N4—N3—Cu1	122.80 (13)	H10A—C10—H10B	109.5
C8—N4—N3	111.35 (17)	C8—C10—H10C	109.5
C8—N4—H4	127.8 (15)	H10A—C10—H10C	109.5
N3—N4—H4	119.9 (15)	H10B—C10—H10C	109.5
C11—O1—Cu1	101.34 (13)	O2—C11—O1	121.5 (2)
C11—O2—Cu1	79.30 (13)	O2—C11—C12	120.4 (2)
C13—O3—Cu1	100.41 (13)	O1—C11—C12	118.11 (19)
C13—O4—Cu1	79.78 (13)	C11—C12—H12A	109.5
N1—C1—C2	109.0 (2)	C11—C12—H12B	109.5
N1—C1—C4	120.58 (19)	H12A—C12—H12B	109.5
C2—C1—C4	130.46 (19)	C11—C12—H12C	109.5
C3—C2—C1	106.30 (19)	H12A—C12—H12C	109.5
C3—C2—H2A	126.8	H12B—C12—H12C	109.5
C1—C2—H2A	126.8	O4—C13—O3	121.95 (19)
N2—C3—C2	106.8 (2)	O4—C13—C14	120.2 (2)
N2—C3—C5	121.5 (2)	O3—C13—C14	117.8 (2)
C2—C3—C5	131.7 (2)	C13—C14—H14A	109.5
C1—C4—H4A	109.5	C13—C14—H14B	109.5
C1—C4—H4B	109.5	H14A—C14—H14B	109.5
H4A—C4—H4B	109.5	C13—C14—H14C	109.5
C1—C4—H4C	109.5	H14A—C14—H14C	109.5
H4A—C4—H4C	109.5	H14B—C14—H14C	109.5
H4B—C4—H4C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4i	0.82 (3)	1.92 (3)	2.726 (3)	166 (3)
N4—H4···O2ii	0.87 (3)	1.91 (3)	2.732 (2)	157 (2)

Table 1

Selected bond lengths (Å)

Cu1—N1	1.9851 (18)
Cu1—N3	1.9925 (16)
Cu1—O1	1.9909 (15)
Cu1—O2	2.4774 (18)
Cu1—O3	2.0045 (14)
Cu1—O4	2.4603 (16)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4i	0.82 (3)	1.92 (3)	2.726 (3)	166 (3)
N4—H4⋯O2ii	0.87 (3)	1.91 (3)	2.732 (2)	157 (2)

Symmetry codes: (i) ; (ii) .