catena-Poly[[[aqua-copper(II)]-bis-[μ-bis-(3,5-dimethyl-1H-pyrazol-4-yl) selenide-κN:N]] dichloride monohydrate].

In the title compound, {[Cu(C(10)H(14)N(4)Se)(2)(H(2)O)]Cl(2)·H(2)O}(n), the Cu(II) ion, lying on a twofold rotation axis, has a square-pyramidal geometry constituted by four N atoms of pyrazolyl groups in the basal plane and an apical O atom of a water mol-ecule. A pair of bis-(3,5-dimethyl-1H-pyrazol-4-yl) selenide ligands bridge the Cu centers into a polymeric double-chain extending along [001]. The chloride anions are involved in inter-molecular N-H⋯Cl and O-H⋯Cl hydrogen bonds, which link the chains into a three-dimensional network.

Related literature

For general background to the applications of coordination polymers, see: Farha et al. (2009 ▶); Shibahara et al. (2007 ▶); Zhang et al. (2009 ▶). For our studies of similar complexes, see: Seredyuk et al. (2007 ▶, 2009 ▶).

Experimental

Crystal data

[Cu(C10H14N4Se)2(H2O)]Cl2·H2O

M = 708.90

Monoclinic,

a = 11.332 (1) Å

b = 13.229 (2) Å

c = 18.786 (1) Å

β = 92.45 (3)°

V = 2813.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.59 mm−1

T = 100 K

0.10 × 0.05 × 0.01 mm

Data collection

Kuma KM-4 CCD diffractometer

6625 measured reflections

2377 independent reflections

2217 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.072

S = 1.10

2377 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.44 e Å−3

Data collection: KM-4 CCD Software. (Kuma Diffraction, 1998 ▶); cell refinement: KM-4 CCD Software.; data reduction: KM-4 CCD Software.; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007403/hy2286sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007403/hy2286Isup2.hkl

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

[Cu(C10H14N4Se)2(H2O)]Cl2·H2O	F(000) = 1420
Mr = 708.90	Dx = 1.673 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6625 reflections
a = 11.332 (1) Å	θ = 3.2–28.4°
b = 13.229 (2) Å	µ = 3.59 mm−1
c = 18.786 (1) Å	T = 100 K
β = 92.45 (3)°	Plates, blue
V = 2813.7 (5) Å3	0.10 × 0.05 × 0.01 mm
Z = 4

Kuma KM-4 CCD diffractometer	2217 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.061
graphite	θmax = 25.0°, θmin = 3.2°
ω scans	h = −13→7
6625 measured reflections	k = −15→15
2377 independent reflections	l = −22→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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0419P)2 + 1.7165P] where P = (Fo2 + 2Fc2)/3
2377 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

	x	y	z	Uiso*/Ueq
C1	−0.0470 (2)	−0.1461 (2)	0.41623 (14)	0.0171 (6)
H22A	0.0111	−0.1105	0.4471	0.026*
H22B	−0.0068	−0.1790	0.3773	0.026*
H22C	−0.0873	−0.1974	0.4440	0.026*
C2	−0.1350 (2)	−0.07273 (19)	0.38631 (13)	0.0112 (5)
C3	0.2414 (2)	0.04235 (18)	0.58358 (13)	0.0106 (5)
C4	−0.2939 (2)	0.02624 (19)	0.36872 (14)	0.0137 (5)
C5	−0.4086 (2)	0.0822 (2)	0.36926 (16)	0.0232 (7)
H9A	−0.4637	0.0538	0.3330	0.035*
H9B	−0.3950	0.1538	0.3589	0.035*
H9C	−0.4421	0.0758	0.4163	0.035*
C6	0.0587 (2)	0.14112 (19)	0.38756 (14)	0.0124 (5)
H5A	0.0236	0.1593	0.3407	0.019*
H5B	0.1033	0.1988	0.4074	0.019*
H5C	−0.0040	0.1230	0.4196	0.019*
C7	0.1401 (2)	0.05297 (19)	0.37995 (13)	0.0106 (5)
C8	0.2365 (2)	0.02232 (19)	0.42508 (13)	0.0115 (5)
C9	0.2796 (2)	−0.0650 (2)	0.39493 (13)	0.0129 (5)
C10	0.3787 (2)	−0.1344 (2)	0.41780 (15)	0.0205 (6)
H14A	0.3463	−0.1955	0.4392	0.031*
H14B	0.4311	−0.1001	0.4529	0.031*
H14C	0.4234	−0.1532	0.3763	0.031*
N1	−0.12324 (17)	−0.02426 (15)	0.32427 (11)	0.0112 (4)
N2	−0.22165 (18)	0.03492 (15)	0.31502 (11)	0.0128 (4)
H2N	−0.2356	0.0742	0.2778	0.015*
N3	0.12555 (17)	−0.01244 (16)	0.32624 (11)	0.0113 (4)
N4	0.21226 (19)	−0.08360 (16)	0.33652 (12)	0.0123 (5)
H4N	0.2223	−0.1354	0.3080	0.015*
O1	0.0000	−0.19654 (18)	0.2500	0.0154 (5)
H1O1	−0.0625	−0.2317	0.2606	0.023*
O1W	−0.5000	−0.1193 (3)	0.2500	0.0387 (8)
H1W	−0.4338	−0.1589	0.2619	0.058*
Cl1	−0.25642 (5)	−0.26253 (5)	0.26925 (3)	0.01824 (17)
Cu1	0.0000	−0.02962 (3)	0.2500	0.00888 (13)
Se1	0.30884 (2)	0.097275 (18)	0.501388 (12)	0.01122 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0139 (12)	0.0217 (15)	0.0161 (14)	0.0071 (11)	0.0043 (11)	0.0059 (10)
C2	0.0097 (11)	0.0122 (12)	0.0116 (13)	−0.0016 (10)	−0.0015 (10)	−0.0020 (10)
C3	0.0099 (11)	0.0106 (12)	0.0114 (13)	−0.0014 (9)	0.0035 (10)	−0.0007 (9)
C4	0.0112 (12)	0.0169 (14)	0.0134 (14)	0.0001 (10)	0.0038 (11)	−0.0019 (10)
C5	0.0174 (14)	0.0321 (17)	0.0204 (15)	0.0133 (12)	0.0048 (12)	0.0067 (12)
C6	0.0120 (12)	0.0111 (13)	0.0139 (13)	0.0018 (10)	0.0005 (10)	−0.0001 (9)
C7	0.0087 (11)	0.0117 (12)	0.0113 (13)	−0.0023 (10)	0.0020 (10)	0.0011 (9)
C8	0.0077 (11)	0.0162 (13)	0.0105 (13)	−0.0012 (10)	0.0007 (10)	−0.0004 (9)
C9	0.0091 (12)	0.0158 (13)	0.0138 (14)	0.0009 (10)	0.0004 (11)	−0.0009 (10)
C10	0.0153 (13)	0.0217 (15)	0.0242 (15)	0.0091 (11)	−0.0030 (12)	−0.0013 (11)
N1	0.0090 (10)	0.0106 (11)	0.0139 (11)	0.0019 (8)	−0.0005 (9)	−0.0001 (8)
N2	0.0118 (10)	0.0162 (11)	0.0103 (11)	0.0042 (9)	−0.0009 (9)	0.0022 (8)
N3	0.0069 (10)	0.0116 (11)	0.0154 (11)	0.0024 (8)	0.0013 (9)	0.0009 (8)
N4	0.0108 (10)	0.0126 (11)	0.0134 (11)	0.0041 (8)	0.0004 (9)	−0.0020 (8)
O1	0.0122 (12)	0.0104 (13)	0.0241 (14)	0.000	0.0053 (11)	0.000
O1W	0.0318 (17)	0.0365 (19)	0.048 (2)	0.000	0.0058 (16)	0.000
Cl1	0.0215 (3)	0.0131 (3)	0.0206 (4)	−0.0055 (2)	0.0061 (3)	−0.0008 (2)
Cu1	0.0069 (2)	0.0108 (2)	0.0089 (2)	0.000	0.00069 (17)	0.000
Se1	0.00924 (16)	0.01421 (17)	0.01027 (17)	−0.00342 (9)	0.00104 (11)	−0.00041 (8)

C1—C2	1.485 (3)	C7—N3	1.334 (3)
C1—H22A	0.9800	C7—C8	1.413 (4)
C1—H22B	0.9800	C8—C9	1.385 (4)
C1—H22C	0.9800	C8—Se1	1.900 (2)
C2—N1	1.342 (3)	C9—N4	1.332 (3)
C2—C3i	1.412 (3)	C9—C10	1.499 (3)
C3—C4i	1.391 (4)	C10—H14A	0.9800
C3—C2i	1.412 (3)	C10—H14B	0.9800
C3—Se1	1.896 (2)	C10—H14C	0.9800
C4—N2	1.331 (3)	N1—N2	1.368 (3)
C4—C3i	1.391 (4)	N2—H2N	0.8800
C4—C5	1.496 (4)	N3—N4	1.368 (3)
C5—H9A	0.9800	N4—H4N	0.8800
C5—H9B	0.9800	O1—H1O1	0.8771
C5—H9C	0.9800	O1W—H1W	0.9337
C6—C7	1.497 (3)	Cu1—N1ii	2.017 (2)
C6—H5A	0.9800	Cu1—N3ii	1.988 (2)
C6—H5B	0.9800	Cu1—O1	2.208 (3)
C6—H5C	0.9800
C2—C1—H22A	109.5	N4—C9—C8	106.9 (2)
C2—C1—H22B	109.5	N4—C9—C10	121.2 (2)
H22A—C1—H22B	109.5	C8—C9—C10	131.8 (2)
C2—C1—H22C	109.5	C9—C10—H14A	109.5
H22A—C1—H22C	109.5	C9—C10—H14B	109.5
H22B—C1—H22C	109.5	H14A—C10—H14B	109.5
N1—C2—C3i	109.3 (2)	C9—C10—H14C	109.5
N1—C2—C1	123.4 (2)	H14A—C10—H14C	109.5
C3i—C2—C1	127.3 (2)	H14B—C10—H14C	109.5
C4i—C3—C2i	106.1 (2)	C2—N1—N2	105.85 (19)
C4i—C3—Se1	126.76 (19)	C2—N1—Cu1	132.97 (17)
C2i—C3—Se1	126.70 (19)	N2—N1—Cu1	121.14 (15)
N2—C4—C3i	106.5 (2)	C4—N2—N1	112.3 (2)
N2—C4—C5	121.7 (2)	C4—N2—H2N	123.9
C3i—C4—C5	131.8 (2)	N1—N2—H2N	123.9
C4—C5—H9A	109.5	C7—N3—N4	105.95 (19)
C4—C5—H9B	109.5	C7—N3—Cu1	132.87 (17)
H9A—C5—H9B	109.5	N4—N3—Cu1	120.69 (16)
C4—C5—H9C	109.5	C9—N4—N3	111.8 (2)
H9A—C5—H9C	109.5	C9—N4—H4N	124.1
H9B—C5—H9C	109.5	N3—N4—H4N	124.1
C7—C6—H5A	109.5	Cu1—O1—H1O1	122.0
C7—C6—H5B	109.5	N3ii—Cu1—N3	166.88 (12)
H5A—C6—H5B	109.5	N3ii—Cu1—N1ii	89.60 (8)
C7—C6—H5C	109.5	N3—Cu1—N1ii	89.94 (8)
H5A—C6—H5C	109.5	N3ii—Cu1—N1	89.94 (8)
H5B—C6—H5C	109.5	N3—Cu1—N1	89.60 (8)
N3—C7—C8	109.6 (2)	N1ii—Cu1—N1	175.97 (11)
N3—C7—C6	121.4 (2)	N3ii—Cu1—O1	96.56 (6)
C8—C7—C6	129.0 (2)	N3—Cu1—O1	96.56 (6)
C9—C8—C7	105.7 (2)	N1ii—Cu1—O1	92.01 (6)
C9—C8—Se1	126.54 (19)	N1—Cu1—O1	92.01 (6)
C7—C8—Se1	126.90 (19)	C3—Se1—C8	103.80 (10)
N3—C7—C8—C9	0.5 (3)	C10—C9—N4—N3	178.6 (2)
C6—C7—C8—C9	178.4 (2)	C7—N3—N4—C9	0.4 (3)
N3—C7—C8—Se1	170.61 (17)	Cu1—N3—N4—C9	−172.60 (17)
C6—C7—C8—Se1	−11.5 (4)	C7—N3—Cu1—N3ii	38.4 (2)
C7—C8—C9—N4	−0.2 (3)	N4—N3—Cu1—N3ii	−150.87 (17)
Se1—C8—C9—N4	−170.41 (18)	C7—N3—Cu1—N1ii	126.3 (2)
C7—C8—C9—C10	−178.7 (3)	N4—N3—Cu1—N1ii	−62.89 (17)
Se1—C8—C9—C10	11.1 (4)	C7—N3—Cu1—N1	−49.7 (2)
C3i—C2—N1—N2	−0.7 (3)	N4—N3—Cu1—N1	121.11 (17)
C1—C2—N1—N2	179.3 (2)	C7—N3—Cu1—O1	−141.6 (2)
C3i—C2—N1—Cu1	−178.10 (17)	N4—N3—Cu1—O1	29.13 (17)
C1—C2—N1—Cu1	2.0 (4)	C2—N1—Cu1—N3ii	143.2 (2)
C3i—C4—N2—N1	−0.1 (3)	N2—N1—Cu1—N3ii	−33.83 (17)
C5—C4—N2—N1	−178.6 (2)	C2—N1—Cu1—N3	−49.9 (2)
C2—N1—N2—C4	0.5 (3)	N2—N1—Cu1—N3	133.06 (17)
Cu1—N1—N2—C4	178.26 (17)	C2—N1—Cu1—O1	46.7 (2)
C8—C7—N3—N4	−0.5 (3)	N2—N1—Cu1—O1	−130.39 (16)
C6—C7—N3—N4	−178.6 (2)	C4i—C3—Se1—C8	102.0 (2)
C8—C7—N3—Cu1	171.23 (17)	C2i—C3—Se1—C8	−87.0 (2)
C6—C7—N3—Cu1	−6.9 (4)	C9—C8—Se1—C3	−92.4 (2)
C8—C9—N4—N3	−0.1 (3)	C7—C8—Se1—C3	99.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···Cl1	0.93	2.43	3.354 (2)	169
O1—H1O1···Cl1	0.88	2.25	3.0702 (10)	156
N2—H2N···Cl1iii	0.88	2.33	3.117 (2)	148
N4—H4N···Cl1ii	0.88	2.27	3.144 (2)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯Cl1	0.93	2.43	3.354 (2)	169
O1—H1O1⋯Cl1	0.88	2.25	3.0702 (10)	156
N2—H2N⋯Cl1i	0.88	2.33	3.117 (2)	148
N4—H4N⋯Cl1ii	0.88	2.27	3.144 (2)	176

Symmetry codes: (i) ; (ii) .