catena-Poly[[copper(II)-bis[μ-bis(3,5-dimethyl-1H-pyrazol-4-yl) selenide]] bis(perchlorate)].

In the title compound, {[Cu(C(10)H(14)N(4)Se)(2)](ClO(4))(2)}(n), the Cu(II) ion is located on a twofold rotation axis and has a tetra-gonally distorted square-planar geometry constituted by four N atoms. A pair of bis(3,5-dimethyl-1H-pyrazol-4-yl) selenide (L) ligands bridges the copper centers into a polymeric chain extending along [001]. The perchlorate anions are involved in inter-molecular N-H⋯O hydrogen bonding, which links the chains into layers parallel to the bc plane.

Related literature

For the potential applications of coordination polymers, see: Farha et al. (2009 ▶); Ohba et al. (2009 ▶); Shibahara et al. (2007 ▶). For our studies of similar complexes with different dimensionality, see Seredyuk et al. (2007 ▶).

Experimental

Crystal data

[Cu(C10H14N4Se)2](ClO4)2

M = 800.86

Monoclinic,

a = 28.398 (6) Å

b = 7.5865 (15) Å

c = 18.517 (4) Å

β = 130.69 (3)°

V = 3025.1 (17) Å3

Z = 4

Mo Kα radiation

μ = 3.36 mm−1

T = 120 K

0.20 × 0.15 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.552, T max = 0.845

13077 measured reflections

3415 independent reflections

2799 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.115

S = 1.04

3415 reflections

191 parameters

H-atom parameters constrained

Δρmax = 2.18 e Å−3

Δρmin = −1.00 e Å−3

Data collection: COLLECT (Bruker–Nonius, 2004 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: DIAMOND (Brandenburg, 2006 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809042056/cv2624sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042056/cv2624Isup2.hkl

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

[Cu(C10H14N4Se)2](ClO4)2	F(000) = 1596
Mr = 800.86	Dx = 1.758 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3400 reflections
a = 28.398 (6) Å	θ = 2.9–27.5°
b = 7.5865 (15) Å	µ = 3.36 mm−1
c = 18.517 (4) Å	T = 120 K
β = 130.69 (3)°	Plates, brown
V = 3025.1 (17) Å3	0.2 × 0.15 × 0.05 mm
Z = 4

Nonius KappaCCD diffractometer	3415 independent reflections
Radiation source: fine-focus sealed tube	2799 reflections with I > 2σ(I)
graphite	Rint = 0.074
ω–scans	θmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −36→34
Tmin = 0.552, Tmax = 0.845	k = −9→9
13077 measured reflections	l = −24→22

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0574P)2 + 8.3063P] where P = (Fo2 + 2Fc2)/3
3415 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 2.18 e Å−3
0 restraints	Δρmin = −1.00 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cu1	0.0000	0.48037 (13)	−0.2500	0.0124 (2)
Se1	0.15222 (2)	0.73993 (6)	0.14892 (4)	0.01476 (14)
Cl1	0.13436 (8)	0.99852 (19)	0.36166 (12)	0.0307 (4)
O1	0.1340 (3)	1.0280 (6)	0.2844 (4)	0.0369 (12)
O2	0.1537 (3)	1.1562 (6)	0.4173 (3)	0.0430 (13)
O3	0.1753 (2)	0.8577 (5)	0.4177 (4)	0.0410 (14)
O4	0.0732 (2)	0.9468 (7)	0.3248 (4)	0.0510 (14)
N1	0.0655 (2)	0.5177 (6)	−0.1109 (3)	0.0144 (10)
N2	0.1167 (2)	0.4166 (6)	−0.0546 (3)	0.0146 (10)
H4	0.1257	0.3301	−0.0755	0.017*
N3	0.0637 (2)	0.5450 (6)	0.2384 (3)	0.0125 (10)
N4	0.1183 (2)	0.4511 (6)	0.2931 (3)	0.0131 (10)
H3	0.1284	0.3739	0.3367	0.016*
C1	0.0190 (3)	0.7707 (8)	−0.0923 (4)	0.0237 (14)
H11A	0.0036	0.8098	−0.1548	0.036*
H11B	0.0367	0.8713	−0.0486	0.036*
H11C	−0.0155	0.7211	−0.0987	0.036*
C2	0.0679 (3)	0.6330 (7)	−0.0538 (4)	0.0141 (12)
C3	0.1216 (3)	0.6022 (7)	0.0402 (4)	0.0128 (12)
C4	0.1526 (3)	0.4643 (7)	0.0377 (4)	0.0146 (11)
C5	0.2128 (3)	0.3741 (9)	0.1141 (5)	0.0268 (15)
H19A	0.2057	0.2792	0.1420	0.040*
H19B	0.2422	0.4595	0.1637	0.040*
H19C	0.2300	0.3245	0.0867	0.040*
C6	0.0155 (3)	0.7705 (8)	0.1110 (5)	0.0217 (14)
H8A	−0.0160	0.7091	0.0508	0.033*
H8B	0.0328	0.8680	0.1000	0.033*
H8C	−0.0035	0.8168	0.1362	0.033*
C7	0.0657 (3)	0.6460 (7)	0.1804 (4)	0.0140 (12)
C8	0.1218 (3)	0.6135 (7)	0.1993 (4)	0.0128 (11)
C9	0.1539 (3)	0.4907 (7)	0.2723 (4)	0.0148 (12)
C10	0.2162 (3)	0.4049 (8)	0.3247 (5)	0.0250 (14)
H17A	0.2105	0.2792	0.3088	0.037*
H17B	0.2407	0.4188	0.3935	0.037*
H17C	0.2380	0.4608	0.3061	0.037*

	U11	U22	U33	U12	U13	U23
Cu1	0.0104 (4)	0.0185 (5)	0.0111 (5)	0.000	0.0082 (4)	0.000
Se1	0.0156 (2)	0.0179 (3)	0.0128 (3)	−0.0062 (2)	0.0101 (3)	−0.0039 (2)
Cl1	0.0342 (8)	0.0231 (7)	0.0390 (9)	0.0019 (7)	0.0258 (8)	0.0063 (7)
O1	0.052 (3)	0.032 (3)	0.038 (3)	−0.003 (2)	0.034 (3)	−0.001 (2)
O2	0.068 (4)	0.030 (2)	0.027 (3)	0.000 (3)	0.029 (3)	0.003 (2)
O3	0.055 (4)	0.022 (2)	0.064 (4)	0.013 (2)	0.048 (3)	0.016 (2)
O4	0.037 (3)	0.070 (4)	0.048 (3)	−0.017 (3)	0.029 (3)	−0.011 (3)
N1	0.015 (3)	0.016 (2)	0.012 (2)	0.002 (2)	0.008 (2)	−0.0016 (18)
N2	0.013 (3)	0.016 (2)	0.012 (2)	0.0048 (19)	0.007 (2)	−0.0009 (18)
N3	0.012 (2)	0.018 (2)	0.010 (2)	0.004 (2)	0.008 (2)	0.0002 (18)
N4	0.011 (2)	0.015 (2)	0.010 (2)	0.0013 (19)	0.005 (2)	0.0022 (17)
C1	0.024 (4)	0.021 (3)	0.017 (3)	0.009 (3)	0.010 (3)	0.001 (2)
C2	0.012 (3)	0.017 (3)	0.016 (3)	0.001 (2)	0.011 (3)	0.001 (2)
C3	0.015 (3)	0.014 (3)	0.011 (3)	−0.003 (2)	0.009 (2)	0.001 (2)
C4	0.015 (3)	0.017 (2)	0.014 (3)	0.001 (2)	0.011 (3)	0.001 (2)
C5	0.021 (4)	0.033 (4)	0.024 (3)	0.007 (3)	0.013 (3)	0.003 (3)
C6	0.015 (3)	0.026 (3)	0.022 (3)	0.004 (3)	0.010 (3)	0.011 (2)
C7	0.017 (3)	0.014 (3)	0.011 (3)	−0.001 (2)	0.009 (3)	−0.001 (2)
C8	0.014 (3)	0.015 (3)	0.010 (3)	−0.001 (2)	0.009 (2)	−0.003 (2)
C9	0.012 (3)	0.017 (3)	0.016 (3)	−0.001 (2)	0.009 (2)	−0.001 (2)
C10	0.020 (3)	0.031 (3)	0.029 (3)	0.006 (3)	0.018 (3)	0.008 (3)

Cu1—N3i	1.967 (5)	C1—H11A	0.9800
Cu1—N3ii	1.967 (5)	C1—H11B	0.9800
Cu1—N1	1.982 (5)	C1—H11C	0.9800
Cu1—N1iii	1.982 (5)	C2—C3	1.396 (8)
Se1—C8	1.893 (5)	C3—C4	1.387 (8)
Se1—C3	1.902 (5)	C4—C5	1.497 (8)
Cl1—O3	1.413 (5)	C5—H19A	0.9800
Cl1—O2	1.434 (5)	C5—H19B	0.9800
Cl1—O1	1.442 (5)	C5—H19C	0.9800
Cl1—O4	1.447 (5)	C6—C7	1.478 (8)
N1—C2	1.339 (7)	C6—H8A	0.9800
N1—N2	1.347 (6)	C6—H8B	0.9800
N2—C4	1.349 (7)	C6—H8C	0.9800
N2—H4	0.8800	C7—C8	1.413 (8)
N3—C7	1.349 (7)	C8—C9	1.386 (8)
N3—N4	1.373 (6)	C9—C10	1.502 (8)
N3—Cu1i	1.967 (5)	C10—H17A	0.9800
N4—C9	1.330 (7)	C10—H17B	0.9800
N4—H3	0.8800	C10—H17C	0.9800
C1—C2	1.497 (8)
N3i—Cu1—N3ii	168.8 (3)	C4—C3—C2	106.5 (5)
N3i—Cu1—N1	91.28 (16)	C4—C3—Se1	126.0 (4)
N3ii—Cu1—N1	90.32 (16)	C2—C3—Se1	127.0 (4)
N3i—Cu1—N1iii	90.32 (16)	N2—C4—C3	105.9 (5)
N3ii—Cu1—N1iii	91.28 (16)	N2—C4—C5	121.9 (5)
N1—Cu1—N1iii	163.6 (3)	C3—C4—C5	132.2 (5)
C8—Se1—C3	101.66 (19)	C4—C5—H19A	109.5
O3—Cl1—O2	110.9 (3)	C4—C5—H19B	109.5
O3—Cl1—O1	108.4 (3)	H19A—C5—H19B	109.5
O2—Cl1—O1	109.5 (3)	C4—C5—H19C	109.5
O3—Cl1—O4	107.6 (3)	H19A—C5—H19C	109.5
O2—Cl1—O4	110.2 (4)	H19B—C5—H19C	109.5
O1—Cl1—O4	110.2 (4)	C7—C6—H8A	109.5
C2—N1—N2	106.7 (5)	C7—C6—H8B	109.5
C2—N1—Cu1	129.9 (4)	H8A—C6—H8B	109.5
N2—N1—Cu1	123.3 (3)	C7—C6—H8C	109.5
N1—N2—C4	111.7 (4)	H8A—C6—H8C	109.5
N1—N2—H4	124.1	H8B—C6—H8C	109.5
C4—N2—H4	124.1	N3—C7—C8	109.2 (5)
C7—N3—N4	105.7 (4)	N3—C7—C6	122.5 (5)
C7—N3—Cu1i	131.4 (4)	C8—C7—C6	128.3 (5)
N4—N3—Cu1i	122.9 (3)	C9—C8—C7	106.1 (5)
C9—N4—N3	112.0 (4)	C9—C8—Se1	126.9 (4)
C9—N4—H3	124.0	C7—C8—Se1	126.3 (4)
N3—N4—H3	124.0	N4—C9—C8	107.1 (5)
C2—C1—H11A	109.5	N4—C9—C10	120.8 (5)
C2—C1—H11B	109.5	C8—C9—C10	132.0 (5)
H11A—C1—H11B	109.5	C9—C10—H17A	109.5
C2—C1—H11C	109.5	C9—C10—H17B	109.5
H11A—C1—H11C	109.5	H17A—C10—H17B	109.5
H11B—C1—H11C	109.5	C9—C10—H17C	109.5
N1—C2—C3	109.1 (5)	H17A—C10—H17C	109.5
N1—C2—C1	121.8 (5)	H17B—C10—H17C	109.5
C3—C2—C1	129.1 (5)
N3i—Cu1—N1—C2	−53.2 (5)	N1—N2—C4—C5	−178.8 (5)
N3ii—Cu1—N1—C2	138.0 (5)	C2—C3—C4—N2	−1.3 (6)
N1iii—Cu1—N1—C2	42.3 (5)	Se1—C3—C4—N2	−174.1 (4)
N3i—Cu1—N1—N2	122.9 (4)	C2—C3—C4—C5	178.5 (6)
N3ii—Cu1—N1—N2	−45.9 (4)	Se1—C3—C4—C5	5.7 (9)
N1iii—Cu1—N1—N2	−141.6 (4)	N4—N3—C7—C8	0.3 (6)
C2—N1—N2—C4	−0.4 (6)	Cu1i—N3—C7—C8	−179.0 (4)
Cu1—N1—N2—C4	−177.3 (4)	N4—N3—C7—C6	−178.8 (5)
C7—N3—N4—C9	0.7 (6)	Cu1i—N3—C7—C6	2.0 (9)
Cu1i—N3—N4—C9	180.0 (4)	N3—C7—C8—C9	−1.0 (6)
N2—N1—C2—C3	−0.4 (6)	C6—C7—C8—C9	177.9 (6)
Cu1—N1—C2—C3	176.2 (4)	N3—C7—C8—Se1	−172.0 (4)
N2—N1—C2—C1	178.4 (5)	C6—C7—C8—Se1	7.0 (9)
Cu1—N1—C2—C1	−5.0 (8)	C3—Se1—C8—C9	97.2 (5)
N1—C2—C3—C4	1.1 (6)	C3—Se1—C8—C7	−93.7 (5)
C1—C2—C3—C4	−177.6 (6)	N3—N4—C9—C8	−1.3 (6)
N1—C2—C3—Se1	173.8 (4)	N3—N4—C9—C10	179.1 (5)
C1—C2—C3—Se1	−4.9 (9)	C7—C8—C9—N4	1.4 (6)
C8—Se1—C3—C4	−91.4 (5)	Se1—C8—C9—N4	172.3 (4)
C8—Se1—C3—C2	97.3 (5)	C7—C8—C9—C10	−179.1 (6)
N1—N2—C4—C3	1.1 (6)	Se1—C8—C9—C10	−8.3 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H4···O3ii	0.88	2.06	2.912 (6)	161
N4—H3···O2iv	0.88	2.02	2.879 (6)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H4⋯O3i	0.88	2.06	2.912 (6)	161
N4—H3⋯O2ii	0.88	2.02	2.879 (6)	166

Symmetry codes: (i) ; (ii) .