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

Wang, J.; Hou, Y.; Fang, Z.

doi:10.1107/S1600536810035440

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1229

doi:10.1107/S1600536810035440

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

Jun Wang,^a ^* Yong Hou ^a and Zhi-li Fang ^b

^aZhongshan Polytechnic, Zhongshan, Guangdong 528404, People's Republic of China, and ^bSchool of Basic Science, East China Jiaotong University, Nanchang 330013, People's Republic of China
^*Correspondence e-mail: wangjun7203@126.com

(Received 31 August 2010; accepted 2 September 2010; online 8 September 2010)

In the title coordination polymer, [Cu(C₂O₄)(C₁₂H₈N₂)]_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 octahedral coordination geometry. The oxalate anions act as bis-bidentate ligands, bridging the Cu–phen units in zigzag chains extending parallel to [100]. Interchain C—H⋯O hydrogen bonding and π–π stacking interactions [centroid–centroid distance = 3.7439 (17) Å] assemble neighboring chains, forming a three-dimensional supramolecular 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_r = 331.76
Orthorhombic, P n a 2₁
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[F² > 2σ(F²)] = 0.024
wR(F²) = 0.059
S = 1.04
2618 reflections
190 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ), 1217 Friedel pairs
Flack parameter: 0.019 (14)

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⋯O4^iv	0.93	2.56	3.072 (3)	115
Symmetry codes: (i) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{5\over 2}}, z]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

The design and construction of metal coordination polymers based on metal ions and multifunctional bridging ligands is of great interest due to their intriguing topologies and potential applications as functional materials (Benneli & Gatteschi, 2002; Qiu et al., 2007). Copper, with its variable coordination numbers and flexible coordination geometry, provides unique opportunities for the discovery of unusual networks in this interesting and challenging field (Qin et al., 2005). We chose oxalate ligands as organic spacers since this rigid molecule has proven to be able to establish a bridge between metal centers. Herein, we present the structure of the title compound, [Cu(C₂O₄)(C₁₂H₈N₂)]_n.

The Cu^II atom exhibits a distorted octahedral configuration coordinated by four oxygen atoms from two oxalate ligands (Cu—O = 1.9753 (18)-2.3135 (18) Å) and two nitrogen atoms from one 1,10-phenanthroline ligand (Cu—N = 2.024 (2) and 2.049 (2) Å) (Fig. 1). The oxalate ligands bridge adjacent Cu-phen units to form a one-dimensional zigzag chain along the a-axis of the unit cell. The Cu—Cu separation is 5.529 (2) Å. Interchain π-π stacking interactions between phen ligands in neighboring chainslead to the formation of sheets of connected chains in the ab-plane. The centroid to centroid distances between neighboring 1,10-phenanthroline ligands is 3.7439 (17) Å [ring (C4-C9) to ring (N2, C1 to C5) (symmetry code: –1/2+x, 3/2–y, z)]. C–H···O hydrogen bonds interconnect these sheets to extend to a three-dimensional supramolecular network motif (Table 1; Fig. 2).

Related literature top

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 top

A sample of cupric acetate (0.0399 g, 0.20 mmol), oxalic acid (0.1015 g, 0.50 mmol), 1,10-phenanthroline (0.2523 g, 0.50 mmol), were added to water (10 ml). The resultant mixture was sealed in a 25 ml stainless steel reactor with a Teflon liner and kept under autogenous pressure at 413 K for 78 h, and then cooled to room temperature at a rate of 0.5 K/min. Colorless blocky crystals of the title compound suitable for single-crystal X-ray diffraction analyses formed in a yield of approximately 65%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP represention of atom numbering diagram for the title complex, showing 30% probability displacement ellipsoids. Symmetry code: (i) –1/2 + x, 2.5–y, z.
	Fig. 2. View of the three-dimensional structure of the title compound.

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

Crystal data top

[Cu(C₂O₄)(C₁₂H₈N₂)]	F(000) = 668
M_r = 331.76	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0289P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2618 reflections	Δρ_max = 0.29 e Å⁻³
190 parameters	Δρ_min = −0.30 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1217 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.019 (14)

Crystal data top

[Cu(C₂O₄)(C₁₂H₈N₂)]	V = 1236.50 (18) Å³
M_r = 331.76	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 9.1445 (8) Å	µ = 1.78 mm⁻¹
b = 10.1443 (9) Å	T = 298 K
c = 13.3294 (11) Å	0.42 × 0.35 × 0.29 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2618 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	2373 reflections with I > 2σ(I)
T_min = 0.544, T_max = 0.612	R_int = 0.021
6811 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.059	Δρ_max = 0.29 e Å⁻³
S = 1.04	Δρ_min = −0.30 e Å⁻³
2618 reflections	Absolute structure: Flack (1983), 1217 Friedel pairs
190 parameters	Absolute structure parameter: 0.019 (14)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry codes: (i) x−1/2, −y+5/2, z; (ii) x+1/2, −y+5/2, z.

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.93	2.49	3.160 (3)	129
C2—H2···O2^v	0.93	2.52	3.136 (3)	124
C1—H1···O4ⁱ	0.93	2.56	3.072 (3)	115

Symmetry codes: (i) x−1/2, −y+5/2, z; (iii) −x+5/2, y−1/2, z+1/2; (iv) x−1/2, −y+3/2, z; (v) −x+3/2, y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₂O₄)(C₁₂H₈N₂)]
M_r	331.76
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	9.1445 (8), 10.1443 (9), 13.3294 (11)
V (Å³)	1236.50 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.78
Crystal size (mm)	0.42 × 0.35 × 0.29

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.544, 0.612
No. of measured, independent and observed [I > 2σ(I)] reflections	6811, 2618, 2373
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.059, 1.04
No. of reflections	2618
No. of parameters	190
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.30
Absolute structure	Flack (1983), 1217 Friedel pairs
Absolute structure parameter	0.019 (14)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O4ⁱ	0.93	2.51	3.416 (4)	165.5
C9—H9···O1ⁱⁱ	0.93	2.49	3.160 (3)	128.9
C2—H2···O2ⁱⁱⁱ	0.93	2.52	3.136 (3)	124.1
C1—H1···O4^iv	0.93	2.56	3.072 (3)	115.2

Symmetry codes: (i) −x+5/2, y−1/2, z+1/2; (ii) x−1/2, −y+3/2, z; (iii) −x+3/2, y−1/2, z−1/2; (iv) x−1/2, −y+5/2, z.

Acknowledgements

This work was supported financially by Zhongshan Polytechnic.

References

Benneli, C. & Gatteschi, D. (2002). Chem. Rev. 102, 2369–2388. Web of Science PubMed Google Scholar
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