catena-Poly[[(1,10-phenanthroline)copper(II)]-μ-oxalato].

In the title coordination polymer, [Cu(C(2)O(4))(C(12)H(8)N(2))](n), the Cu(II) atom is six-coordinated by four O atoms from two oxalate ligands and two N atoms from one 1,10-phenanthroline (phen) ligand in a distorted octa-hedral coordination geometry. The oxalate anions act as bis-bidentate ligands, bridging the Cu-phen units in zigzag chains extending parallel to [100]. Inter-chain C-H⋯O hydrogen bonding and π-π stacking inter-actions [centroid-centroid distance = 3.7439 (17) Å] assemble neighboring chains, forming a three-dimensional supra-molecular network.

Related literature

For the topologies and potential applications as functional materials of metal coordination polymers, see: Benneli & Gatteschi (2002 ▶); Qin et al. (2005 ▶); Qiu et al. (2007 ▶).

Experimental

Crystal data

[Cu(C2O4)(C12H8N2)]

M = 331.76

Orthorhombic,

a = 9.1445 (8) Å

b = 10.1443 (9) Å

c = 13.3294 (11) Å

V = 1236.50 (18) Å3

Z = 4

Mo Kα radiation

μ = 1.78 mm−1

T = 298 K

0.42 × 0.35 × 0.29 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.544, T max = 0.612

6811 measured reflections

2618 independent reflections

2373 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.059

S = 1.04

2618 reflections

190 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 1217 Friedel pairs

Flack parameter: 0.019 (14)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035440/zl2304sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035440/zl2304Isup2.hkl

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

[Cu(C2O4)(C12H8N2)]	F(000) = 668
Mr = 331.76	Dx = 1.782 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2618 reflections
a = 9.1445 (8) Å	θ = 2.5–27.0°
b = 10.1443 (9) Å	µ = 1.78 mm−1
c = 13.3294 (11) Å	T = 298 K
V = 1236.50 (18) Å3	Block, blue
Z = 4	0.42 × 0.35 × 0.29 mm

Bruker APEXII CCD area-detector diffractometer	2618 independent reflections
Radiation source: fine-focus sealed tube	2373 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scan	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −8→11
Tmin = 0.544, Tmax = 0.612	k = −10→12
6811 measured reflections	l = −16→15

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)] = 0.024	H-atom parameters constrained
wR(F2) = 0.059	w = 1/[σ2(Fo2) + (0.0289P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2618 reflections	Δρmax = 0.28 e Å−3
190 parameters	Δρmin = −0.30 e Å−3
1 restraint	Absolute structure: Flack (1983), 1217 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.019 (14)

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
C1	0.6938 (3)	0.9764 (3)	−0.04988 (19)	0.0407 (6)
H1	0.6652	1.0617	−0.0662	0.049*
Cu1	0.87241 (3)	1.09675 (2)	0.11815 (4)	0.03062 (9)
N1	0.9474 (2)	0.9310 (2)	0.18929 (17)	0.0352 (5)
O1	1.0814 (2)	1.12990 (18)	0.02682 (14)	0.0377 (4)
C2	0.6422 (3)	0.8724 (3)	−0.1095 (2)	0.0486 (7)
H2	0.5818	0.8883	−0.1643	0.058*
N2	0.7802 (2)	0.9598 (2)	0.02762 (16)	0.0325 (4)
O2	0.98329 (19)	1.21773 (18)	0.20589 (13)	0.0377 (4)
C3	0.6829 (3)	0.7475 (3)	−0.0849 (2)	0.0472 (7)
H3	0.6506	0.6770	−0.1237	0.057*
O3	1.1635 (2)	1.36277 (17)	0.21108 (14)	0.0358 (4)
C4	0.7727 (3)	0.7242 (2)	−0.0022 (2)	0.0386 (6)
O4	1.2795 (2)	1.25638 (18)	0.04136 (14)	0.0376 (4)
C5	0.8190 (3)	0.8351 (2)	0.05270 (19)	0.0321 (5)
C6	0.9086 (2)	0.8194 (2)	0.13957 (17)	0.0307 (6)
C7	0.9518 (3)	0.6918 (3)	0.1703 (2)	0.0404 (6)
C8	0.9027 (3)	0.5816 (2)	0.1130 (4)	0.0500 (7)
H8	0.9293	0.4971	0.1330	0.060*
C9	0.8186 (4)	0.5967 (2)	0.0306 (3)	0.0485 (7)
H9	0.7899	0.5226	−0.0055	0.058*
C10	1.0386 (3)	0.6850 (3)	0.2567 (2)	0.0498 (7)
H10	1.0723	0.6038	0.2794	0.060*
C11	1.0740 (4)	0.7970 (3)	0.3077 (3)	0.0555 (8)
H11	1.1295	0.7922	0.3660	0.067*
C12	1.0266 (3)	0.9184 (3)	0.2720 (2)	0.0471 (7)
H12	1.0515	0.9940	0.3076	0.056*
C13	1.1578 (3)	1.2130 (2)	0.07154 (19)	0.0303 (5)
C14	1.0979 (3)	1.2700 (2)	0.17167 (19)	0.0288 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0439 (15)	0.0420 (14)	0.0362 (14)	0.0018 (12)	−0.0088 (12)	−0.0036 (12)
Cu1	0.03102 (14)	0.02964 (14)	0.03119 (13)	−0.00071 (10)	−0.00153 (13)	−0.00414 (16)
N1	0.0315 (11)	0.0393 (11)	0.0347 (12)	0.0005 (9)	−0.0041 (9)	−0.0007 (9)
O1	0.0370 (10)	0.0409 (9)	0.0350 (10)	−0.0020 (8)	0.0025 (8)	−0.0107 (8)
C2	0.0555 (19)	0.0558 (17)	0.0346 (15)	0.0010 (14)	−0.0120 (13)	−0.0089 (13)
N2	0.0336 (10)	0.0323 (10)	0.0317 (11)	0.0008 (8)	−0.0013 (9)	−0.0039 (9)
O2	0.0365 (11)	0.0433 (10)	0.0335 (10)	−0.0101 (8)	0.0092 (8)	−0.0118 (9)
C3	0.0500 (18)	0.0539 (17)	0.0376 (16)	−0.0090 (14)	−0.0026 (14)	−0.0157 (13)
O3	0.0382 (10)	0.0329 (9)	0.0361 (10)	−0.0043 (8)	0.0007 (8)	−0.0064 (8)
C4	0.0393 (14)	0.0370 (13)	0.0395 (15)	−0.0068 (11)	0.0064 (11)	−0.0096 (12)
O4	0.0363 (10)	0.0388 (9)	0.0377 (10)	−0.0026 (8)	0.0102 (8)	−0.0030 (8)
C5	0.0320 (13)	0.0337 (13)	0.0307 (13)	−0.0018 (11)	0.0058 (11)	−0.0035 (10)
C6	0.0288 (12)	0.0328 (12)	0.0305 (16)	0.0004 (9)	0.0055 (9)	−0.0016 (9)
C7	0.0375 (14)	0.0414 (15)	0.0424 (15)	0.0040 (12)	0.0059 (12)	0.0067 (12)
C8	0.0599 (17)	0.0306 (12)	0.0593 (18)	0.0031 (10)	0.011 (2)	0.0032 (18)
C9	0.0581 (18)	0.0317 (15)	0.056 (2)	−0.0092 (12)	0.0074 (16)	−0.0072 (13)
C10	0.0491 (18)	0.0495 (18)	0.0509 (19)	0.0092 (13)	0.0012 (14)	0.0111 (14)
C11	0.0519 (19)	0.068 (2)	0.0465 (19)	0.0056 (17)	−0.0099 (15)	0.0107 (17)
C12	0.0499 (17)	0.0496 (16)	0.0417 (16)	0.0011 (13)	−0.0124 (13)	−0.0052 (13)
C13	0.0327 (13)	0.0285 (12)	0.0296 (12)	0.0062 (10)	−0.0010 (11)	0.0017 (10)
C14	0.0293 (12)	0.0297 (12)	0.0274 (12)	0.0011 (10)	−0.0030 (10)	−0.0022 (11)

C1—N2	1.311 (3)	O3—Cu1ii	2.3135 (18)
C1—C2	1.403 (4)	C4—C5	1.407 (3)
C1—H1	0.9300	C4—C9	1.428 (4)
Cu1—O2	1.9753 (18)	O4—C13	1.263 (3)
Cu1—O4i	1.9973 (19)	O4—Cu1ii	1.9973 (19)
Cu1—N2	2.024 (2)	C5—C6	1.428 (3)
Cu1—N1	2.049 (2)	C6—C7	1.414 (3)
Cu1—O1	2.2909 (19)	C7—C10	1.401 (4)
Cu1—O3i	2.3135 (18)	C7—C8	1.426 (5)
N1—C12	1.325 (4)	C8—C9	1.350 (6)
N1—C6	1.359 (3)	C8—H8	0.9300
O1—C13	1.247 (3)	C9—H9	0.9300
C2—C3	1.360 (5)	C10—C11	1.363 (4)
C2—H2	0.9300	C10—H10	0.9300
N2—C5	1.356 (3)	C11—C12	1.390 (4)
O2—C14	1.260 (3)	C11—H11	0.9300
C3—C4	1.395 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.554 (3)
O3—C14	1.234 (3)
N2—C1—C2	123.5 (2)	C3—C4—C9	124.7 (3)
N2—C1—H1	118.3	C5—C4—C9	118.4 (3)
C2—C1—H1	118.3	C13—O4—Cu1ii	118.13 (17)
O2—Cu1—O4i	93.34 (8)	N2—C5—C4	122.6 (2)
O2—Cu1—N2	173.31 (8)	N2—C5—C6	117.0 (2)
O4i—Cu1—N2	91.68 (9)	C4—C5—C6	120.4 (2)
O2—Cu1—N1	93.68 (8)	N1—C6—C7	123.3 (2)
O4i—Cu1—N1	172.68 (8)	N1—C6—C5	116.9 (2)
N2—Cu1—N1	81.49 (9)	C7—C6—C5	119.8 (2)
O2—Cu1—O1	78.18 (7)	C10—C7—C6	116.2 (2)
O4i—Cu1—O1	88.46 (7)	C10—C7—C8	125.5 (3)
N2—Cu1—O1	97.55 (7)	C6—C7—C8	118.3 (3)
N1—Cu1—O1	95.01 (8)	C9—C8—C7	121.7 (3)
O2—Cu1—O3i	89.80 (7)	C9—C8—H8	119.1
O4i—Cu1—O3i	77.92 (7)	C7—C8—H8	119.1
N2—Cu1—O3i	95.57 (7)	C8—C9—C4	121.3 (3)
N1—Cu1—O3i	100.03 (8)	C8—C9—H9	119.3
O1—Cu1—O3i	161.33 (6)	C4—C9—H9	119.3
C12—N1—C6	117.9 (2)	C11—C10—C7	120.2 (3)
C12—N1—Cu1	130.30 (19)	C11—C10—H10	119.9
C6—N1—Cu1	111.77 (16)	C7—C10—H10	119.9
C13—O1—Cu1	108.21 (16)	C10—C11—C12	119.6 (3)
C3—C2—C1	118.2 (3)	C10—C11—H11	120.2
C3—C2—H2	120.9	C12—C11—H11	120.2
C1—C2—H2	120.9	N1—C12—C11	122.7 (3)
C1—N2—C5	118.1 (2)	N1—C12—H12	118.6
C1—N2—Cu1	129.22 (18)	C11—C12—H12	118.6
C5—N2—Cu1	112.62 (16)	O1—C13—O4	125.2 (2)
C14—O2—Cu1	118.30 (16)	O1—C13—C14	117.7 (2)
C2—C3—C4	120.6 (3)	O4—C13—C14	117.1 (2)
C2—C3—H3	119.7	O3—C14—O2	124.9 (2)
C4—C3—H3	119.7	O3—C14—C13	118.5 (2)
C14—O3—Cu1ii	108.00 (16)	O2—C14—C13	116.6 (2)
C3—C4—C5	116.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4iii	0.93	2.51	3.416 (4)	166
C9—H9···O1iv	0.93	2.49	3.160 (3)	129
C2—H2···O2v	0.93	2.52	3.136 (3)	124
C1—H1···O4i	0.93	2.56	3.072 (3)	115

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O4i	0.93	2.51	3.416 (4)	166
C9—H9⋯O1ii	0.93	2.49	3.160 (3)	129
C2—H2⋯O2iii	0.93	2.52	3.136 (3)	124
C1—H1⋯O4iv	0.93	2.56	3.072 (3)	115

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .