catena-Poly[[[diaqua-copper(II)]-bis-[μ-1,1'-(butane-1,4-di-yl)diimidazole-κN:N]] dinitrate].

In the title compound, {[Cu(C(10)H(14)N(4))(2)(H(2)O)(2)](NO(3))(2)}(n), the Cu(II) ion lies on an inversion center and is six-coordinated in an octa-hedral environment by four N atoms from four different 1,1'-butane-1,4-diyldiimidazole ligands and two O atoms from the two water mol-ecules. Bridging by the ligands results in a ribbon structure. Adjacent ribbons are linked to the nitrate anions via O-H⋯O hydrogen bonds, forming layers. One nitrate O atom is disordered equally over two positions.

Related literature

For background and the synthesis of 1,1′-butane-1,4-diyldiimidazole, see: Ma et al. (2003 ▶). For the crystal structure of a metal adduct, see: Che et al. (2006 ▶).

Experimental

Crystal data

[Cu(C10H14N4)2(H2O)2](NO3)2

M = 604.10

Monoclinic,

a = 22.161 (11) Å

b = 10.334 (4) Å

c = 14.366 (7) Å

β = 126.375 (18)°

V = 2649 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.89 mm−1

T = 291 (2) K

0.48 × 0.36 × 0.25 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.673, T max = 0.808

12704 measured reflections

3023 independent reflections

2753 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.113

S = 1.07

3023 reflections

188 parameters

H-atom parameters constrained

Δρmax = 0.82 e Å−3

Δρmin = −0.55 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027281/ng2477sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027281/ng2477Isup2.hkl

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

[Cu(C10H14N4)2(H2O)2](NO3)2	F000 = 1260
Mr = 604.10	Dx = 1.515 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 11099 reflections
a = 22.161 (11) Å	θ = 3.3–27.5º
b = 10.334 (4) Å	µ = 0.89 mm−1
c = 14.366 (7) Å	T = 291 (2) K
β = 126.375 (18)º	Block, blue
V = 2649 (2) Å3	0.48 × 0.36 × 0.25 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3023 independent reflections
Radiation source: fine-focus sealed tube	2753 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
T = 291(2) K	θmax = 27.5º
ω scans	θmin = 3.3º
Absorption correction: Multi-scan(ABSCOR; Higashi, 1995)	h = −28→28
Tmin = 0.673, Tmax = 0.808	k = −13→12
12704 measured reflections	l = −18→18

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0644P)2 + 3.5066P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3023 reflections	Δρmax = 0.82 e Å−3
188 parameters	Δρmin = −0.55 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	Occ. (<1)
C1	0.43494 (12)	0.5667 (2)	0.87357 (19)	0.0360 (4)
H1	0.4387	0.4802	0.8600	0.043*
C2	0.40800 (13)	0.6108 (2)	0.9310 (2)	0.0395 (5)
H2	0.3901	0.5611	0.9638	0.047*
C3	0.44106 (11)	0.7749 (2)	0.87476 (18)	0.0321 (4)
H3	0.4495	0.8593	0.8627	0.038*
C4	0.38590 (14)	0.8327 (3)	0.9787 (2)	0.0460 (6)
H4A	0.4039	0.9190	0.9807	0.055*
H4B	0.4069	0.8078	1.0576	0.055*
C5	0.30100 (14)	0.8355 (3)	0.9086 (2)	0.0514 (7)
H5A	0.2872	0.8926	0.9467	0.062*
H5B	0.2836	0.7493	0.9084	0.062*
C6	0.26042 (14)	0.8803 (3)	0.7830 (2)	0.0473 (6)
H6A	0.2128	0.9186	0.7569	0.057*
H6B	0.2902	0.9470	0.7804	0.057*
C7	0.24623 (12)	0.7730 (2)	0.70083 (18)	0.0394 (5)
H7A	0.2938	0.7405	0.7214	0.047*
H7B	0.2205	0.7023	0.7082	0.047*
C8	0.22282 (12)	0.9038 (3)	0.5330 (2)	0.0427 (5)
H8	0.2696	0.9427	0.5699	0.051*
C9	0.16308 (12)	0.9201 (3)	0.42203 (19)	0.0402 (5)
H9	0.1619	0.9731	0.3687	0.048*
C10	0.12939 (11)	0.7874 (2)	0.49805 (18)	0.0325 (4)
H10	0.1010	0.7315	0.5086	0.039*
Cu1	0.5000	0.66433 (3)	0.7500	0.02769 (13)
N1	0.45588 (9)	0.67011 (16)	0.83845 (14)	0.0293 (4)
N2	0.41221 (9)	0.74259 (19)	0.93120 (14)	0.0328 (4)
N3	0.20075 (10)	0.81828 (18)	0.58036 (16)	0.0342 (4)
N4	0.10424 (9)	0.84658 (17)	0.39970 (15)	0.0317 (4)
N5	0.59796 (14)	0.1501 (2)	0.7259 (3)	0.0516 (6)
O1	0.5000	0.9027 (3)	0.7500	0.0740 (10)
H11	0.4628	0.9523	0.7254	0.111*
O2	0.5825 (2)	0.0978 (4)	0.6366 (3)	0.1229 (13)
O3	0.5894 (5)	0.2662 (7)	0.7011 (8)	0.089 (2)	0.50
O4	0.61485 (19)	0.0723 (3)	0.8025 (3)	0.0997 (10)
O5	0.5000	0.4120 (3)	0.7500	0.0640 (8)
H12	0.4690	0.3573	0.7433	0.082 (13)*
O3'	0.6140 (5)	0.2592 (7)	0.7753 (9)	0.099 (3)	0.50

	U11	U22	U33	U12	U13	U23
C1	0.0384 (11)	0.0388 (11)	0.0349 (10)	0.0060 (9)	0.0239 (9)	0.0065 (9)
C2	0.0400 (11)	0.0502 (13)	0.0353 (11)	0.0056 (10)	0.0263 (10)	0.0109 (10)
C3	0.0270 (9)	0.0405 (11)	0.0284 (9)	−0.0014 (8)	0.0162 (8)	−0.0031 (8)
C4	0.0390 (12)	0.0706 (17)	0.0274 (11)	0.0129 (11)	0.0191 (10)	−0.0063 (10)
C5	0.0388 (12)	0.089 (2)	0.0311 (12)	0.0203 (12)	0.0233 (11)	0.0022 (11)
C6	0.0419 (12)	0.0596 (14)	0.0324 (11)	0.0185 (11)	0.0178 (10)	0.0020 (11)
C7	0.0314 (10)	0.0485 (13)	0.0256 (10)	0.0068 (9)	0.0099 (9)	0.0054 (9)
C8	0.0284 (10)	0.0633 (15)	0.0339 (11)	−0.0104 (10)	0.0170 (9)	−0.0013 (10)
C9	0.0313 (10)	0.0588 (14)	0.0309 (10)	−0.0083 (10)	0.0187 (9)	0.0017 (10)
C10	0.0263 (9)	0.0397 (10)	0.0281 (10)	−0.0016 (8)	0.0144 (8)	0.0021 (8)
Cu1	0.02036 (18)	0.0421 (2)	0.02152 (19)	0.000	0.01289 (15)	0.000
N1	0.0239 (8)	0.0408 (9)	0.0241 (8)	0.0015 (6)	0.0147 (7)	−0.0004 (6)
N2	0.0254 (8)	0.0509 (10)	0.0216 (8)	0.0055 (7)	0.0135 (7)	−0.0009 (7)
N3	0.0252 (8)	0.0453 (10)	0.0258 (9)	0.0011 (7)	0.0116 (7)	0.0020 (7)
N4	0.0249 (8)	0.0436 (9)	0.0260 (8)	−0.0019 (7)	0.0147 (7)	0.0002 (7)
N5	0.0477 (12)	0.0460 (12)	0.0739 (17)	0.0010 (9)	0.0430 (13)	0.0065 (11)
O1	0.098 (2)	0.0383 (14)	0.134 (3)	0.000	0.095 (3)	0.000
O2	0.162 (3)	0.137 (3)	0.090 (2)	−0.032 (3)	0.086 (3)	−0.006 (2)
O3	0.112 (6)	0.045 (3)	0.150 (7)	0.023 (4)	0.098 (6)	0.024 (5)
O4	0.109 (2)	0.108 (2)	0.0686 (16)	−0.0290 (19)	0.0449 (16)	0.0012 (16)
O5	0.086 (2)	0.0417 (14)	0.097 (2)	0.000	0.072 (2)	0.000
O3'	0.085 (5)	0.043 (3)	0.158 (8)	0.002 (3)	0.066 (6)	0.001 (5)

C1—C2	1.352 (3)	C8—C9	1.349 (3)
C1—N1	1.374 (3)	C8—N3	1.370 (3)
C1—H1	0.9300	C8—H8	0.9300
C2—N2	1.365 (3)	C9—N4	1.372 (3)
C2—H2	0.9300	C9—H9	0.9300
C3—N1	1.325 (3)	C10—N4	1.322 (3)
C3—N2	1.339 (3)	C10—N3	1.335 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—N2	1.465 (3)	Cu1—N1	2.0120 (18)
C4—C5	1.519 (4)	Cu1—N1i	2.0120 (18)
C4—H4A	0.9700	Cu1—N4ii	2.020 (2)
C4—H4B	0.9700	Cu1—N4iii	2.020 (2)
C5—C6	1.535 (3)	Cu1—O1	2.463 (3)
C5—H5A	0.9700	Cu1—O5	2.608 (3)
C5—H5B	0.9700	N4—Cu1ii	2.0203 (19)
C6—C7	1.510 (3)	N5—O4	1.228 (4)
C6—H6A	0.9700	N5—O3	1.234 (7)
C6—H6B	0.9700	N5—O2	1.239 (4)
C7—N3	1.470 (3)	O1—H11	0.8500
C7—H7A	0.9700	O5—H12	0.8500
C7—H7B	0.9700
C2—C1—N1	109.2 (2)	C8—C9—H9	125.1
C2—C1—H1	125.4	N4—C9—H9	125.1
N1—C1—H1	125.4	N4—C10—N3	111.30 (19)
C1—C2—N2	106.46 (19)	N4—C10—H10	124.3
C1—C2—H2	126.8	N3—C10—H10	124.3
N2—C2—H2	126.8	N1—Cu1—N1i	176.60 (10)
N1—C3—N2	110.72 (19)	N1—Cu1—N4ii	89.82 (8)
N1—C3—H3	124.6	N1i—Cu1—N4ii	90.37 (8)
N2—C3—H3	124.6	N1—Cu1—N4iii	90.37 (8)
N2—C4—C5	112.4 (2)	N1i—Cu1—N4iii	89.82 (8)
N2—C4—H4A	109.1	N4ii—Cu1—N4iii	173.60 (10)
C5—C4—H4A	109.1	N1—Cu1—O1	88.30 (5)
N2—C4—H4B	109.1	N1i—Cu1—O1	88.30 (5)
C5—C4—H4B	109.1	N4ii—Cu1—O1	93.20 (5)
H4A—C4—H4B	107.8	N4iii—Cu1—O1	93.20 (5)
C4—C5—C6	114.7 (2)	N1—Cu1—O5	91.70 (5)
C4—C5—H5A	108.6	N1i—Cu1—O5	91.70 (5)
C6—C5—H5A	108.6	N4ii—Cu1—O5	86.80 (5)
C4—C5—H5B	108.6	N4iii—Cu1—O5	86.80 (5)
C6—C5—H5B	108.6	O1—Cu1—O5	180.000 (1)
H5A—C5—H5B	107.6	C3—N1—C1	105.91 (18)
C7—C6—C5	113.8 (2)	C3—N1—Cu1	126.85 (14)
C7—C6—H6A	108.8	C1—N1—Cu1	127.24 (14)
C5—C6—H6A	108.8	C3—N2—C2	107.66 (18)
C7—C6—H6B	108.8	C3—N2—C4	126.1 (2)
C5—C6—H6B	108.8	C2—N2—C4	126.2 (2)
H6A—C6—H6B	107.7	C10—N3—C8	107.36 (18)
N3—C7—C6	111.5 (2)	C10—N3—C7	126.27 (19)
N3—C7—H7A	109.3	C8—N3—C7	126.33 (19)
C6—C7—H7A	109.3	C10—N4—C9	105.44 (18)
N3—C7—H7B	109.3	C10—N4—Cu1ii	127.10 (15)
C6—C7—H7B	109.3	C9—N4—Cu1ii	127.43 (15)
H7A—C7—H7B	108.0	O4—N5—O3	144.0 (5)
C9—C8—N3	106.16 (19)	O4—N5—O2	113.1 (3)
C9—C8—H8	126.9	O3—N5—O2	103.0 (5)
N3—C8—H8	126.9	Cu1—O1—H11	127.1
C8—C9—N4	109.7 (2)	Cu1—O5—H12	131.6

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11···O4iv	0.85	1.96	2.801 (4)	170
O5—H12···O3i	0.85	2.10	2.888 (8)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H11⋯O4i	0.85	1.96	2.801 (4)	170
O5—H12⋯O3ii	0.85	2.10	2.888 (8)	153

Symmetry codes: (i) ; (ii) .