catena-Poly[[bis-(3-carb-oxy-5-nitro-benzoato-κO)copper(II)]-μ-1,3-di-4-pyridylpropane-κN:N'].

In the title compound, [Cu(C(8)H(4)NO(6))(2)(C(13)H(14)N(2))](n), the square-planar coordinated Cu(II) ion lies on an inversion centre and is coordinated by two protonated 5-nitro-isophthalate ligands. The Cu(II) ions are linked into a one-dimensional coordination polymer by tethering 1,3-di-4-pyridylpropane ligands, whose central methyl-ene C atoms are situated on twofold rotation axes. The chains are oriented parallel to the c axis, and stack into a supra-molecular three-dimensional structure through O-H⋯O hydrogen-bonding inter-actions.

Related literature

For some recent divalent copper dicarboxyl­ate coordination polymers containing 1,3-di-4-pyridylpropane, see: Wang et al. (2009 ▶).

Experimental

Crystal data

[Cu(C8H4NO6)2(C13H14N2)]

M = 682.05

Monoclinic,

a = 25.2976 (8) Å

b = 5.3702 (2) Å

c = 21.3122 (7) Å

β = 115.865 (2)°

V = 2605.29 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.92 mm−1

T = 173 K

0.22 × 0.22 × 0.11 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.821, T max = 0.905

10349 measured reflections

2401 independent reflections

2087 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.112

S = 1.08

2401 reflections

213 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.10 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalMaker (Palmer, 2007 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031821/tk2526sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031821/tk2526Isup2.hkl

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

[Cu(C8H4NO6)2(C13H14N2)]	F(000) = 1396
Mr = 682.05	Dx = 1.739 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 10349 reflections
a = 25.2976 (8) Å	θ = 1.8–25.4°
b = 5.3702 (2) Å	µ = 0.92 mm−1
c = 21.3122 (7) Å	T = 173 K
β = 115.865 (2)°	Block, blue
V = 2605.29 (15) Å3	0.22 × 0.22 × 0.11 mm
Z = 4

Bruker APEXII diffractometer	2401 independent reflections
Radiation source: fine-focus sealed tube	2087 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω and φ scans	θmax = 25.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −30→28
Tmin = 0.821, Tmax = 0.905	k = −6→6
10349 measured reflections	l = −24→25

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0535P)2 + 8.8582P] where P = (Fo2 + 2Fc2)/3
2401 reflections	(Δ/σ)max < 0.001
213 parameters	Δρmax = 1.10 e Å−3
1 restraint	Δρmin = −0.31 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	Occ. (<1)
Cu1	0.0000	0.0000	0.0000	0.01865 (18)
O1	0.07835 (8)	−0.1413 (4)	0.04676 (10)	0.0209 (5)
O2	0.11395 (9)	0.1584 (4)	0.00388 (11)	0.0273 (5)
O3	0.31946 (10)	0.1103 (5)	0.04659 (13)	0.0332 (6)
H3A	0.3473 (12)	0.154 (7)	0.0365 (19)	0.040*
O4	0.37815 (10)	−0.2063 (5)	0.10363 (13)	0.0374 (6)
O5	0.30010 (10)	−0.7828 (4)	0.22279 (12)	0.0325 (6)
O6	0.20769 (10)	−0.7829 (4)	0.19827 (11)	0.0279 (5)
N1	0.01902 (10)	0.2420 (5)	0.07966 (12)	0.0207 (5)
N2	0.25020 (11)	−0.6974 (5)	0.19249 (12)	0.0222 (6)
C1	0.17873 (12)	−0.1639 (6)	0.07286 (14)	0.0180 (6)
C2	0.22615 (12)	−0.0740 (6)	0.06286 (14)	0.0178 (6)
H2	0.2213	0.0694	0.0348	0.021*
C3	0.28055 (12)	−0.1922 (6)	0.09360 (14)	0.0189 (6)
C4	0.28838 (12)	−0.3992 (6)	0.13549 (14)	0.0187 (6)
H4	0.3252	−0.4823	0.1562	0.022*
C5	0.24125 (13)	−0.4817 (5)	0.14633 (14)	0.0187 (6)
C6	0.18627 (12)	−0.3712 (6)	0.11546 (14)	0.0178 (6)
H6	0.1545	−0.4349	0.1231	0.021*
C7	0.11985 (12)	−0.0359 (6)	0.03800 (14)	0.0190 (6)
C8	0.33175 (12)	−0.0985 (6)	0.08267 (15)	0.0230 (7)
C11	0.06442 (14)	0.2091 (7)	0.14297 (17)	0.0299 (7)
H11	0.0897	0.0709	0.1492	0.036*
C12	0.07641 (14)	0.3641 (7)	0.19921 (16)	0.0300 (8)
H12	0.1088	0.3305	0.2428	0.036*
C13	0.04037 (13)	0.5719 (6)	0.19170 (16)	0.0255 (7)
C14	−0.00464 (13)	0.6150 (6)	0.12500 (16)	0.0270 (7)
H14	−0.0290	0.7579	0.1164	0.032*
C15	−0.01359 (13)	0.4504 (6)	0.07206 (16)	0.0265 (7)
H15	−0.0445	0.4844	0.0274	0.032*
C16	0.05196 (14)	0.7391 (7)	0.25328 (16)	0.0297 (7)
H16A	0.0841	0.8549	0.2586	0.036*
H16B	0.0662	0.6344	0.2957	0.036*
C17	0.0000	0.8934 (9)	0.2500	0.0293 (10)
H17A	−0.0137	1.0023	0.2084	0.035*	0.50
H17B	0.0137	1.0023	0.2916	0.035*	0.50

	U11	U22	U33	U12	U13	U23
Cu1	0.0127 (3)	0.0208 (3)	0.0223 (3)	0.0016 (2)	0.0075 (2)	−0.0009 (2)
O1	0.0152 (9)	0.0220 (12)	0.0241 (10)	0.0019 (9)	0.0072 (8)	0.0005 (9)
O2	0.0225 (10)	0.0269 (13)	0.0338 (12)	0.0092 (10)	0.0135 (9)	0.0115 (10)
O3	0.0267 (12)	0.0337 (14)	0.0471 (14)	0.0025 (11)	0.0235 (11)	0.0139 (12)
O4	0.0198 (11)	0.0438 (15)	0.0491 (14)	0.0036 (11)	0.0153 (10)	0.0089 (12)
O5	0.0296 (12)	0.0306 (14)	0.0346 (12)	0.0131 (10)	0.0116 (10)	0.0145 (11)
O6	0.0330 (12)	0.0236 (12)	0.0294 (11)	−0.0015 (10)	0.0158 (10)	0.0040 (10)
N1	0.0171 (12)	0.0233 (14)	0.0213 (12)	0.0037 (11)	0.0079 (10)	0.0006 (11)
N2	0.0278 (14)	0.0191 (14)	0.0196 (12)	0.0036 (11)	0.0103 (11)	0.0000 (10)
C1	0.0160 (13)	0.0193 (15)	0.0174 (13)	0.0025 (12)	0.0061 (11)	−0.0026 (12)
C2	0.0197 (14)	0.0177 (15)	0.0157 (13)	0.0016 (12)	0.0075 (11)	0.0016 (11)
C3	0.0177 (14)	0.0212 (16)	0.0172 (13)	0.0008 (12)	0.0071 (11)	−0.0022 (12)
C4	0.0152 (13)	0.0203 (15)	0.0173 (13)	0.0032 (12)	0.0039 (11)	−0.0017 (12)
C5	0.0223 (14)	0.0176 (15)	0.0139 (13)	0.0015 (12)	0.0059 (11)	0.0002 (12)
C6	0.0161 (13)	0.0194 (16)	0.0173 (13)	−0.0022 (12)	0.0066 (11)	−0.0038 (12)
C7	0.0169 (14)	0.0216 (17)	0.0158 (13)	0.0018 (12)	0.0046 (11)	−0.0030 (12)
C8	0.0175 (14)	0.0279 (17)	0.0222 (15)	−0.0001 (13)	0.0072 (12)	−0.0001 (13)
C11	0.0274 (16)	0.0300 (19)	0.0332 (17)	0.0041 (14)	0.0142 (14)	0.0028 (15)
C12	0.0304 (17)	0.032 (2)	0.0257 (16)	−0.0019 (15)	0.0105 (13)	0.0022 (14)
C13	0.0227 (15)	0.0277 (18)	0.0283 (16)	−0.0034 (13)	0.0129 (13)	0.0012 (14)
C14	0.0239 (15)	0.0255 (18)	0.0327 (17)	−0.0002 (14)	0.0133 (13)	0.0007 (14)
C15	0.0217 (15)	0.0339 (19)	0.0236 (15)	0.0000 (14)	0.0098 (13)	0.0031 (14)
C16	0.0268 (17)	0.034 (2)	0.0261 (16)	−0.0030 (15)	0.0092 (13)	−0.0004 (14)
C17	0.033 (2)	0.030 (3)	0.025 (2)	0.000	0.0131 (19)	0.000

Cu1—O1	1.9427 (19)	C3—C8	1.500 (4)
Cu1—O1i	1.9427 (19)	C4—C5	1.383 (4)
Cu1—N1i	2.022 (2)	C4—H4	0.9500
Cu1—N1	2.022 (2)	C5—C6	1.386 (4)
O1—C7	1.276 (3)	C6—H6	0.9500
O2—C7	1.243 (4)	C11—C12	1.380 (5)
O3—C8	1.318 (4)	C11—H11	0.9500
O3—H3A	0.85 (4)	C12—C13	1.405 (5)
O4—C8	1.206 (4)	C12—H12	0.9500
O5—N2	1.229 (3)	C13—C14	1.399 (4)
O6—N2	1.224 (3)	C13—C16	1.510 (5)
N1—C11	1.349 (4)	C14—C15	1.372 (5)
N1—C15	1.358 (4)	C14—H14	0.9500
N2—C5	1.472 (4)	C15—H15	0.9500
C1—C2	1.393 (4)	C16—C17	1.529 (4)
C1—C6	1.396 (4)	C16—H16A	0.9900
C1—C7	1.509 (4)	C16—H16B	0.9900
C2—C3	1.392 (4)	C17—C16ii	1.530 (4)
C2—H2	0.9500	C17—H17A	0.9900
C3—C4	1.385 (4)	C17—H17B	0.9900
O1—Cu1—O1i	180.00 (11)	O2—C7—C1	120.7 (3)
O1—Cu1—N1i	89.75 (9)	O1—C7—C1	115.1 (3)
O1i—Cu1—N1i	90.25 (9)	O4—C8—O3	124.6 (3)
O1—Cu1—N1	90.25 (9)	O4—C8—C3	123.3 (3)
O1i—Cu1—N1	89.75 (9)	O3—C8—C3	112.1 (2)
N1i—Cu1—N1	180.0	N1—C11—C12	124.0 (3)
C7—O1—Cu1	118.18 (18)	N1—C11—H11	118.0
C8—O3—H3A	112 (3)	C12—C11—H11	118.0
C11—N1—C15	115.8 (3)	C11—C12—C13	119.6 (3)
C11—N1—Cu1	122.9 (2)	C11—C12—H12	120.2
C15—N1—Cu1	121.3 (2)	C13—C12—H12	120.2
O6—N2—O5	123.6 (3)	C14—C13—C12	116.5 (3)
O6—N2—C5	118.5 (2)	C14—C13—C16	123.2 (3)
O5—N2—C5	117.9 (2)	C12—C13—C16	120.2 (3)
C2—C1—C6	119.6 (3)	C15—C14—C13	119.9 (3)
C2—C1—C7	119.9 (3)	C15—C14—H14	120.1
C6—C1—C7	120.6 (2)	C13—C14—H14	120.1
C3—C2—C1	120.7 (3)	N1—C15—C14	124.0 (3)
C3—C2—H2	119.7	N1—C15—H15	118.0
C1—C2—H2	119.7	C14—C15—H15	118.0
C4—C3—C2	120.2 (3)	C13—C16—C17	116.5 (2)
C4—C3—C8	118.6 (3)	C13—C16—H16A	108.2
C2—C3—C8	121.2 (3)	C17—C16—H16A	108.2
C5—C4—C3	118.3 (3)	C13—C16—H16B	108.2
C5—C4—H4	120.9	C17—C16—H16B	108.2
C3—C4—H4	120.9	H16A—C16—H16B	107.3
C4—C5—C6	122.9 (3)	C16—C17—C16ii	114.4 (4)
C4—C5—N2	118.1 (3)	C16—C17—H17A	108.7
C6—C5—N2	118.9 (3)	C16ii—C17—H17A	108.7
C5—C6—C1	118.3 (3)	C16—C17—H17B	108.7
C5—C6—H6	120.9	C16ii—C17—H17B	108.7
C1—C6—H6	120.9	H17A—C17—H17B	107.6
O2—C7—O1	124.2 (3)
N1i—Cu1—O1—C7	94.8 (2)	Cu1—O1—C7—C1	−176.93 (17)
N1—Cu1—O1—C7	−85.2 (2)	C2—C1—C7—O2	−4.5 (4)
O1—Cu1—N1—C11	−17.8 (2)	C6—C1—C7—O2	175.1 (3)
O1i—Cu1—N1—C11	162.2 (2)	C2—C1—C7—O1	175.8 (2)
O1—Cu1—N1—C15	161.9 (2)	C6—C1—C7—O1	−4.6 (4)
O1i—Cu1—N1—C15	−18.1 (2)	C4—C3—C8—O4	6.5 (5)
C6—C1—C2—C3	1.5 (4)	C2—C3—C8—O4	−173.9 (3)
C7—C1—C2—C3	−178.9 (3)	C4—C3—C8—O3	−174.8 (3)
C1—C2—C3—C4	−1.0 (4)	C2—C3—C8—O3	4.8 (4)
C1—C2—C3—C8	179.4 (3)	C15—N1—C11—C12	4.0 (5)
C2—C3—C4—C5	−0.8 (4)	Cu1—N1—C11—C12	−176.3 (2)
C8—C3—C4—C5	178.9 (3)	N1—C11—C12—C13	−0.7 (5)
C3—C4—C5—C6	2.1 (4)	C11—C12—C13—C14	−3.1 (5)
C3—C4—C5—N2	−178.3 (2)	C11—C12—C13—C16	178.3 (3)
O6—N2—C5—C4	−174.7 (3)	C12—C13—C14—C15	3.4 (5)
O5—N2—C5—C4	4.8 (4)	C16—C13—C14—C15	−178.0 (3)
O6—N2—C5—C6	5.0 (4)	C11—N1—C15—C14	−3.6 (4)
O5—N2—C5—C6	−175.5 (3)	Cu1—N1—C15—C14	176.7 (2)
C4—C5—C6—C1	−1.5 (4)	C13—C14—C15—N1	−0.1 (5)
N2—C5—C6—C1	178.8 (2)	C14—C13—C16—C17	24.3 (5)
C2—C1—C6—C5	−0.3 (4)	C12—C13—C16—C17	−157.2 (3)
C7—C1—C6—C5	−179.9 (2)	C13—C16—C17—C16ii	62.0 (2)
Cu1—O1—C7—O2	3.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2iii	0.85 (4)	1.86 (2)	2.668 (3)	158 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2i	0.85 (4)	1.86 (2)	2.668 (3)	158 (4)

Symmetry code: (i) .