catena-Poly[[[diaqua-copper(II)]-bis-[μ-1,5-bis-(1H-imidazol-1-yl)pentane-κ(2) N (3):N (3')]] naphthalene-1,5-disulfonate].

In the title complex, {[Cu(C11H16N4)2(H2O)2](C10H6O6S2)} n , the Cu(II) atom, lying on an inversion center, is six-coordinated by two water mol-ecules and four N atoms from four 1,5-bis-(1H-imidazol-1-yl)pentane (biim-5) ligands in a distorted octa-hedral geometry. Adjacent Cu(II) atoms are linked by two biim-5 ligands, forming a chain along [111]. Two atoms of the pentane group are disordered over two sets of sites, with an occupancy ratio of 0.554 (18):0.446 (18). Inter-molecular O-H⋯O hydrogen bonds link the chains and the centrosymmetric naphthalene-1,5-disulfonate anions into a layer structure parallel to (0-11).

Related literature

For background to metal-organic coordination polymers with N-donor ligands, see: Kesanli et al. (2005 ▶); Wei et al. (2008 ▶); Zhang et al. (2010 ▶).

Experimental

Crystal data

[Cu(C11H16N4)2(H2O)2](C10H6O6S2)

M = 790.37

Triclinic,

a = 9.300 (5) Å

b = 9.880 (5) Å

c = 11.020 (5) Å

α = 95.490 (5)°

β = 102.930 (5)°

γ = 114.000 (5)°

V = 881.5 (8) Å3

Z = 1

Mo Kα radiation

μ = 0.80 mm−1

T = 293 K

0.41 × 0.33 × 0.21 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.970, T max = 0.980

8706 measured reflections

3995 independent reflections

2218 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.167

S = 1.03

3995 reflections

258 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.62 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812045679/hy2599sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045679/hy2599Isup2.hkl

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

[Cu(C11H16N4)2(H2O)2](C10H6O6S2)	Z = 1
Mr = 790.37	F(000) = 411
Triclinic, P1	Dx = 1.489 Mg m−3
Hall symbol: -P 1	Melting point: not measured K
a = 9.300 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.880 (5) Å	Cell parameters from 3995 reflections
c = 11.020 (5) Å	θ = 3.0–27.5°
α = 95.490 (5)°	µ = 0.80 mm−1
β = 102.930 (5)°	T = 293 K
γ = 114.000 (5)°	Block, blue
V = 881.5 (8) Å3	0.41 × 0.33 × 0.21 mm

Rigaku R-AXIS RAPID diffractometer	3995 independent reflections
Radiation source: fine-focus sealed tube	2218 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
Detector resolution: 10 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −12→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→12
Tmin = 0.970, Tmax = 0.980	l = −13→14
8706 measured reflections

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)] = 0.074	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.167	w = 1/[σ2(Fo2) + (0.0505P)2 + 1.4149P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3995 reflections	Δρmax = 0.52 e Å−3
258 parameters	Δρmin = −0.62 e Å−3
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (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	Occ. (<1)
Cu	0.5000	0.5000	0.5000	0.0421 (3)
C1	0.2899 (6)	0.3794 (7)	0.2360 (5)	0.0641 (17)
H1	0.1991	0.3656	0.2646	0.077*
C2	0.5349 (6)	0.4438 (6)	0.2291 (5)	0.0485 (13)
H2	0.6490	0.4841	0.2538	0.058*
C3	0.4368 (7)	0.3741 (8)	0.1108 (5)	0.0675 (18)
H3	0.4693	0.3573	0.0391	0.081*
C4	0.1318 (13)	0.1980 (15)	0.0189 (10)	0.053 (4)	0.554 (18)
H4A	0.1603	0.1171	−0.0048	0.063*	0.554 (18)
H4B	0.0399	0.1584	0.0543	0.063*	0.554 (18)
C5	0.0905 (13)	0.2632 (15)	−0.0932 (11)	0.058 (4)	0.554 (18)
H5A	0.1793	0.2974	−0.1322	0.069*	0.554 (18)
H5B	0.0664	0.3470	−0.0694	0.069*	0.554 (18)
C4'	0.1284 (16)	0.305 (2)	0.0057 (13)	0.056 (5)	0.446 (18)
H4'1	0.0332	0.2855	0.0362	0.068*	0.446 (18)
H4'2	0.1494	0.3908	−0.0355	0.068*	0.446 (18)
C5'	0.1049 (18)	0.1697 (19)	−0.0814 (16)	0.065 (5)	0.446 (18)
H5'1	0.1007	0.0890	−0.0365	0.078*	0.446 (18)
H5'2	0.1929	0.1935	−0.1212	0.078*	0.446 (18)
C6	−0.0690 (7)	0.1223 (9)	−0.1858 (6)	0.082 (2)
C7	−0.1086 (8)	0.2045 (7)	−0.2907 (6)	0.078 (2)
H7A	−0.1019	0.3000	−0.2517	0.094*
H7B	−0.0273	0.2267	−0.3370	0.094*
C8	−0.2770 (7)	0.1114 (6)	−0.3822 (5)	0.0565 (15)
H8A	−0.3585	0.0944	−0.3364	0.068*
H8B	−0.2967	0.1679	−0.4461	0.068*
C9	−0.2189 (6)	−0.0582 (6)	−0.5301 (5)	0.0482 (13)
H9	−0.1436	0.0150	−0.5605	0.058*
C11	−0.3937 (6)	−0.1703 (6)	−0.4280 (5)	0.0445 (12)
H11	−0.4599	−0.1853	−0.3738	0.053*
C10	−0.2722 (6)	−0.2088 (6)	−0.5604 (5)	0.0511 (13)
H10	−0.2386	−0.2577	−0.6164	0.061*
C12	0.4074 (6)	0.7806 (6)	1.1100 (5)	0.0474 (13)
H12	0.3943	0.7151	1.1664	0.057*
C13	0.2935 (6)	0.7343 (5)	0.9885 (5)	0.0432 (12)
H13	0.2051	0.6385	0.9657	0.052*
C14	0.3102 (5)	0.8269 (5)	0.9041 (4)	0.0349 (11)
C15	0.4423 (5)	0.9768 (5)	0.9385 (4)	0.0366 (11)
C16	0.4633 (6)	1.0791 (6)	0.8548 (4)	0.0422 (12)
H16	0.3876	1.0500	0.7748	0.051*
N2	0.2814 (6)	0.3331 (7)	0.1160 (4)	0.0786 (18)
N1	0.4413 (5)	0.4466 (4)	0.3081 (4)	0.0413 (10)
N3	−0.2978 (5)	−0.0341 (4)	−0.4455 (4)	0.0411 (10)
N4	−0.3829 (5)	−0.2802 (5)	−0.4970 (4)	0.0426 (10)
O1	0.0560 (4)	0.6024 (4)	0.7469 (4)	0.0597 (10)
O2	0.2596 (4)	0.7717 (4)	0.6604 (3)	0.0529 (10)
O3	0.0816 (4)	0.8556 (4)	0.7419 (3)	0.0544 (10)
S1	0.16398 (15)	0.75847 (15)	0.75061 (12)	0.0442 (4)
O1W	0.2295 (5)	0.5212 (5)	0.4900 (4)	0.0657 (12)
H1A	0.217 (7)	0.588 (6)	0.542 (5)	0.099*
H1B	0.144 (5)	0.486 (7)	0.420 (3)	0.099*

	U11	U22	U33	U12	U13	U23
Cu	0.0430 (5)	0.0387 (5)	0.0300 (5)	0.0065 (4)	0.0085 (4)	−0.0002 (3)
C1	0.035 (3)	0.098 (5)	0.038 (3)	0.015 (3)	0.009 (3)	−0.007 (3)
C2	0.036 (3)	0.062 (4)	0.037 (3)	0.016 (2)	0.007 (2)	0.000 (2)
C3	0.055 (3)	0.102 (5)	0.032 (3)	0.025 (3)	0.015 (3)	−0.006 (3)
C4	0.054 (6)	0.051 (8)	0.035 (7)	0.012 (5)	0.002 (5)	0.004 (5)
C5	0.057 (7)	0.049 (8)	0.047 (8)	0.017 (6)	−0.007 (6)	0.004 (5)
C4'	0.046 (7)	0.068 (12)	0.039 (9)	0.023 (7)	−0.006 (6)	−0.007 (7)
C5'	0.074 (10)	0.046 (9)	0.061 (11)	0.034 (8)	−0.011 (8)	−0.009 (7)
C6	0.054 (4)	0.104 (6)	0.046 (4)	0.018 (4)	−0.020 (3)	−0.015 (3)
C7	0.070 (4)	0.050 (4)	0.074 (4)	−0.004 (3)	0.019 (4)	−0.027 (3)
C8	0.072 (4)	0.045 (3)	0.053 (3)	0.027 (3)	0.016 (3)	0.010 (3)
C9	0.049 (3)	0.046 (3)	0.045 (3)	0.012 (2)	0.021 (3)	0.009 (2)
C11	0.041 (3)	0.044 (3)	0.040 (3)	0.012 (2)	0.009 (2)	0.005 (2)
C10	0.054 (3)	0.050 (3)	0.048 (3)	0.017 (3)	0.027 (3)	0.005 (2)
C12	0.057 (3)	0.042 (3)	0.044 (3)	0.018 (3)	0.022 (3)	0.013 (2)
C13	0.042 (3)	0.032 (3)	0.048 (3)	0.010 (2)	0.016 (2)	0.002 (2)
C14	0.027 (2)	0.038 (3)	0.035 (2)	0.012 (2)	0.008 (2)	−0.001 (2)
C15	0.033 (2)	0.038 (3)	0.037 (2)	0.016 (2)	0.0092 (19)	0.003 (2)
C16	0.045 (3)	0.043 (3)	0.036 (3)	0.019 (2)	0.008 (2)	0.007 (2)
N2	0.038 (2)	0.133 (5)	0.030 (2)	0.016 (3)	0.001 (2)	−0.015 (3)
N1	0.038 (2)	0.042 (2)	0.036 (2)	0.0116 (18)	0.0102 (19)	0.0011 (17)
N3	0.040 (2)	0.038 (2)	0.035 (2)	0.0113 (19)	0.0035 (18)	0.0040 (17)
N4	0.046 (2)	0.040 (2)	0.036 (2)	0.0132 (19)	0.0129 (19)	0.0054 (18)
O1	0.048 (2)	0.045 (2)	0.059 (2)	0.0027 (17)	0.0022 (18)	0.0011 (17)
O2	0.052 (2)	0.059 (2)	0.042 (2)	0.0200 (18)	0.0161 (17)	−0.0015 (16)
O3	0.044 (2)	0.062 (2)	0.057 (2)	0.0268 (19)	0.0090 (18)	0.0094 (18)
S1	0.0364 (7)	0.0429 (8)	0.0408 (7)	0.0108 (6)	0.0052 (6)	−0.0013 (5)
O1W	0.055 (2)	0.068 (3)	0.059 (3)	0.028 (2)	−0.001 (2)	−0.015 (2)

Cu—N4i	1.988 (4)	C8—N3	1.453 (6)
Cu—N1	2.021 (4)	C8—H8A	0.9700
Cu—O1W	2.587 (5)	C8—H8B	0.9700
C1—N1	1.302 (6)	C9—C10	1.343 (7)
C1—N2	1.331 (7)	C9—N3	1.367 (6)
C1—H1	0.9300	C9—H9	0.9300
C2—C3	1.339 (7)	C11—N4	1.316 (6)
C2—N1	1.368 (6)	C11—N3	1.339 (6)
C2—H2	0.9300	C11—H11	0.9300
C3—N2	1.350 (7)	C10—N4	1.368 (6)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.49 (2)	C12—C16ii	1.360 (7)
C4—N2	1.553 (11)	C12—C13	1.406 (7)
C4—H4A	0.9700	C12—H12	0.9300
C4—H4B	0.9700	C13—C14	1.355 (6)
C5—C6	1.597 (12)	C13—H13	0.9300
C5—H5A	0.9700	C14—C15	1.432 (6)
C5—H5B	0.9700	C14—S1	1.781 (4)
C4'—C5'	1.48 (3)	C15—C16	1.417 (6)
C4'—N2	1.555 (14)	C15—C15ii	1.425 (9)
C4'—H4'1	0.9700	C16—C12ii	1.360 (7)
C4'—H4'2	0.9700	C16—H16	0.9300
C5'—C6	1.615 (15)	N4—Cuiii	1.988 (4)
C5'—H5'1	0.9700	O1—S1	1.448 (4)
C5'—H5'2	0.9700	O2—S1	1.457 (4)
C6—C7	1.537 (10)	O3—S1	1.449 (4)
C7—C8	1.504 (7)	O1W—H1A	0.89 (6)
C7—H7A	0.9700	O1W—H1B	0.89 (4)
C7—H7B	0.9700
N4i—Cu—N4iv	180.000 (1)	N3—C8—C7	112.9 (5)
N4i—Cu—N1v	91.92 (16)	N3—C8—H8A	109.0
N4iv—Cu—N1v	88.08 (16)	C7—C8—H8A	109.0
N4i—Cu—N1	88.08 (16)	N3—C8—H8B	109.0
N4iv—Cu—N1	91.92 (16)	C7—C8—H8B	109.0
N1v—Cu—N1	180.000 (1)	H8A—C8—H8B	107.8
O1W—Cu—N1	91.80 (17)	C10—C9—N3	106.1 (5)
O1W—Cu—N4iv	91.02 (18)	C10—C9—H9	127.0
O1W—Cu—N4i	88.98 (18)	N3—C9—H9	127.0
O1W—Cu—O1Wv	180.00	N4—C11—N3	111.7 (5)
O1W—Cu—N1v	88.20 (17)	N4—C11—H11	124.2
N1—C1—N2	111.5 (5)	N3—C11—H11	124.2
N1—C1—H1	124.3	C9—C10—N4	110.3 (5)
N2—C1—H1	124.3	C9—C10—H10	124.8
C3—C2—N1	109.5 (5)	N4—C10—H10	124.8
C3—C2—H2	125.3	C16ii—C12—C13	120.1 (5)
N1—C2—H2	125.3	C16ii—C12—H12	120.0
C2—C3—N2	106.4 (5)	C13—C12—H12	120.0
C2—C3—H3	126.8	C14—C13—C12	121.2 (4)
N2—C3—H3	126.8	C14—C13—H13	119.4
C5—C4—N2	104.6 (10)	C12—C13—H13	119.4
C5—C4—H4A	110.8	C13—C14—C15	120.5 (4)
N2—C4—H4A	110.8	C13—C14—S1	118.6 (4)
C5—C4—H4B	110.8	C15—C14—S1	120.9 (4)
N2—C4—H4B	110.8	C16—C15—C15ii	119.2 (5)
H4A—C4—H4B	108.9	C16—C15—C14	122.7 (4)
C4—C5—C6	102.3 (10)	C15ii—C15—C14	118.1 (5)
C4—C5—H5A	111.3	C12ii—C16—C15	120.9 (5)
C6—C5—H5A	111.3	C12ii—C16—H16	119.5
C4—C5—H5B	111.3	C15—C16—H16	119.5
C6—C5—H5B	111.3	C1—N2—C3	107.3 (4)
H5A—C5—H5B	109.2	C1—N2—C4	125.1 (6)
C5'—C4'—N2	102.7 (13)	C3—N2—C4	122.1 (6)
C5'—C4'—H4'1	111.2	C1—N2—C4'	120.2 (7)
N2—C4'—H4'1	111.2	C3—N2—C4'	127.6 (7)
C5'—C4'—H4'2	111.2	C1—N1—C2	105.4 (4)
N2—C4'—H4'2	111.2	C1—N1—Cu	122.5 (4)
H4'1—C4'—H4'2	109.1	C2—N1—Cu	131.1 (3)
C4'—C5'—C6	103.8 (12)	C11—N3—C9	106.9 (4)
C4'—C5'—H5'1	111.0	C11—N3—C8	126.2 (5)
C6—C5'—H5'1	111.0	C9—N3—C8	126.8 (5)
C4'—C5'—H5'2	111.0	C11—N4—C10	105.0 (4)
C6—C5'—H5'2	111.0	C11—N4—Cuiii	126.0 (4)
H5'1—C5'—H5'2	109.0	C10—N4—Cuiii	129.0 (4)
C7—C6—C5	97.8 (7)	O1—S1—O3	113.4 (2)
C7—C6—C5'	128.2 (9)	O1—S1—O2	112.4 (2)
C8—C7—C6	112.0 (5)	O3—S1—O2	113.0 (2)
C8—C7—H7A	109.2	O1—S1—C14	105.8 (2)
C6—C7—H7A	109.2	O3—S1—C14	105.9 (2)
C8—C7—H7B	109.2	O2—S1—C14	105.5 (2)
C6—C7—H7B	109.2	H1A—O1W—H1B	107 (5)
H7A—C7—H7B	107.9
N1—C2—C3—N2	−0.1 (7)	C5—C4—N2—C4'	28.3 (11)
N2—C4—C5—C6	−177.0 (7)	C5'—C4'—N2—C1	−142.0 (11)
N2—C4'—C5'—C6	171.5 (9)	C5'—C4'—N2—C3	66.1 (17)
C4—C5—C6—C7	175.4 (10)	C5'—C4'—N2—C4	−31.9 (11)
C4—C5—C6—C5'	−34.7 (13)	N2—C1—N1—C2	0.5 (7)
C4'—C5'—C6—C7	70.9 (16)	N2—C1—N1—Cu	−169.3 (4)
C4'—C5'—C6—C5	31.7 (12)	C3—C2—N1—C1	−0.2 (7)
C5—C6—C7—C8	−167.3 (7)	C3—C2—N1—Cu	168.3 (4)
C5'—C6—C7—C8	170.4 (9)	N4i—Cu—N1—C1	61.3 (5)
C6—C7—C8—N3	−59.1 (7)	N4iv—Cu—N1—C1	−118.7 (5)
N3—C9—C10—N4	0.1 (6)	N4i—Cu—N1—C2	−105.5 (5)
C16ii—C12—C13—C14	0.5 (8)	N4iv—Cu—N1—C2	74.5 (5)
C12—C13—C14—C15	−2.0 (7)	N4—C11—N3—C9	−0.7 (5)
C12—C13—C14—S1	178.4 (4)	N4—C11—N3—C8	−178.5 (4)
C13—C14—C15—C16	−178.6 (5)	C10—C9—N3—C11	0.3 (5)
S1—C14—C15—C16	0.9 (6)	C10—C9—N3—C8	178.1 (5)
C13—C14—C15—C15ii	2.1 (8)	C7—C8—N3—C11	111.1 (6)
S1—C14—C15—C15ii	−178.3 (4)	C7—C8—N3—C9	−66.2 (7)
C15ii—C15—C16—C12ii	0.8 (8)	N3—C11—N4—C10	0.7 (5)
C14—C15—C16—C12ii	−178.5 (5)	N3—C11—N4—Cuiii	179.0 (3)
N1—C1—N2—C3	−0.5 (8)	C9—C10—N4—C11	−0.5 (6)
N1—C1—N2—C4	153.4 (8)	C9—C10—N4—Cuiii	−178.7 (3)
N1—C1—N2—C4'	−157.5 (9)	C13—C14—S1—O1	−3.7 (5)
C2—C3—N2—C1	0.3 (8)	C15—C14—S1—O1	176.8 (4)
C2—C3—N2—C4	−154.5 (8)	C13—C14—S1—O3	117.0 (4)
C2—C3—N2—C4'	155.1 (10)	C15—C14—S1—O3	−62.6 (4)
C5—C4—N2—C1	125.9 (9)	C13—C14—S1—O2	−123.0 (4)
C5—C4—N2—C3	−83.8 (12)	C15—C14—S1—O2	57.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2	0.89 (6)	1.97 (6)	2.836 (6)	163 (6)
O1W—H1B···O1vi	0.89 (4)	2.11 (4)	3.001 (6)	178 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O2	0.89 (6)	1.97 (6)	2.836 (6)	163 (6)
O1W—H1B⋯O1i	0.89 (4)	2.11 (4)	3.001 (6)	178 (7)

Symmetry code: (i) .