catena-Poly[[diformatocopper(II)]-μ-1,4-bis­(imidazol-1-yl)benzene]

Chen, B.

doi:10.1107/S1600536811024019

metal-organic compounds

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Volume 67| Part 7| July 2011| Page m996

doi:10.1107/S1600536811024019

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catena-Poly[[diformatocopper(II)]-μ-1,4-bis(imidazol-1-yl)benzene]

Bang Chen ^a ^*

^aKey Laboratory of Synthetic and Natural Functional Molecule Chemistry (Ministry of Education), College of Chemistry & Materials Science, Northwest University, Xi'an 710069, People's Republic of China
^*Correspondence e-mail: nwuchem@126.com

(Received 31 March 2011; accepted 19 June 2011; online 30 June 2011)

In the title compound, [Cu(CHO₂)₂(C₁₂H₁₀N₄)], the Cu^II ion lies on an inversion center and is coordinated by two formate O atoms and two N atoms from two 1,4-bis(imidazol-1-yl)phenyl ligands (L), forming a square-planar coordination environment. The linear molecule L acts as a bidente bridging ligand, connecting the metal atoms into a chain along [101].

Related literature

For background to coordination polymers containing imidazole-derived ligands, see: Cui et al. (2005 ); Jin et al. (2008 ); Li et al. (2009 ).

Experimental

Crystal data

[Cu(CHO₂)₂(C₁₂H₁₀N₄)]
M_r = 363.82
Monoclinic, P 2₁ /c
a = 8.0971 (16) Å
b = 10.426 (2) Å
c = 8.5723 (17) Å
β = 107.02 (3)°
V = 692.0 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.61 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Rigaku Mercury CCD area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.624, T_max = 0.725
6003 measured reflections
1204 independent reflections
1108 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.075
S = 1.11
1204 reflections
106 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811024019/rn2086sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024019/rn2086Isup2.hkl

checkCIF report

Comment top

Imidazole has been extensively used in crystal engineering, and a large number of imidazole-containing flexible ligands have been extensively studied (Cui et al., 2005; Jin et al., 2008). However, to our knowledge, the research on imidazole ligands bearing rigid spacers is still less developed (Li et al., 2009). For the title compound, the geometry of the Cu^II ion is bound by two imidazole rings of individual L ligands and two formate ions forming a square planar coordination environment (Fig. 1). Notably, as shown in Fig. 2, the four-coordinate Cu^II center is bridged by the linear ligand L to form an infinite one-dimensional chain along the [101] direction.

Related literature top

For background to coordination polymers containing imidazole-derived ligands, see: Cui et al. (2005); Jin et al. (2008); Li et al. (2009).

Experimental top

A mixture of CH₃OH and H₂O (1:1, 8 ml), as a buffer layer, was carefully layered over a solution of Cu(HCO₂)₂ in H₂O (6 ml). Then a solution of 1,4-bis(imidazol-1-yl)phenyl (L, 0.06 mmol) in CH₃OH (6 ml) was layered over the buffer layer, and the resultant reaction was left to stand at room temperature. After ca. three weeks, blue block single crystals appeared at the boundary. Yield: ~25% (based on L).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radius (symmetry codes: A = 1-x, 1-y, -z; B = 1+x, y, -1+z; C = -x, 1-y, 1-z.).
	Fig. 2. The crystal packing for (I).

catena-Poly[[diformatocopper(II)]-µ-1,4-bis(imidazol-1-yl)benzene] top

Crystal data top

[Cu(CHO₂)₂(C₁₂H₁₀N₄)]	F(000) = 370
M_r = 363.82	D_x = 1.746 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.0971 (16) Å	Cell parameters from 2022 reflections
b = 10.426 (2) Å	θ = 2.0–27.9°
c = 8.5723 (17) Å	µ = 1.61 mm⁻¹
β = 107.02 (3)°	T = 293 K
V = 692.0 (2) Å³	Block, blue
Z = 2	0.30 × 0.25 × 0.20 mm

Data collection top

Rigaku Mercury CCD area-detector diffractometer	1204 independent reflections
Radiation source: fine-focus sealed tube	1108 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 9 pixels mm^-1	θ_max = 25.0°, θ_min = 3.3°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→12
T_min = 0.624, T_max = 0.725	l = −10→10
6003 measured reflections

Refinement top

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0452P)² + 0.4041P] where P = (F_o² + 2F_c²)/3
1204 reflections	(Δ/σ)_max < 0.001
106 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Cu(CHO₂)₂(C₁₂H₁₀N₄)]	V = 692.0 (2) Å³
M_r = 363.82	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0971 (16) Å	µ = 1.61 mm⁻¹
b = 10.426 (2) Å	T = 293 K
c = 8.5723 (17) Å	0.30 × 0.25 × 0.20 mm
β = 107.02 (3)°

Data collection top

Rigaku Mercury CCD area-detector diffractometer	1204 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1108 reflections with I > 2σ(I)
T_min = 0.624, T_max = 0.725	R_int = 0.026
6003 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.11	Δρ_max = 0.40 e Å⁻³
1204 reflections	Δρ_min = −0.39 e Å⁻³
106 parameters

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
Cu1	0.5000	0.5000	0.0000	0.01074 (16)
O2	0.3615 (2)	0.73953 (14)	−0.05814 (18)	0.0215 (4)
O1	0.55129 (17)	0.64376 (14)	0.15185 (16)	0.0154 (3)
N2	0.1326 (2)	0.44066 (17)	0.24042 (19)	0.0116 (4)
N1	0.3015 (2)	0.45187 (17)	0.0816 (2)	0.0128 (4)
C7	0.4602 (3)	0.73795 (19)	0.0823 (3)	0.0168 (4)
H7	0.4686	0.8130	0.1427	0.020*
C4	0.0645 (3)	0.4692 (2)	0.3731 (2)	0.0123 (4)
C3	0.0710 (2)	0.35192 (19)	0.1173 (2)	0.0142 (4)
H3	−0.0238	0.2981	0.1032	0.017*
C2	0.1769 (3)	0.35939 (19)	0.0218 (2)	0.0146 (4)
H2	0.1673	0.3097	−0.0706	0.018*
C6	−0.1121 (3)	0.4657 (2)	0.3490 (2)	0.0142 (4)
H6	−0.1864	0.4419	0.2482	0.017*
C1	0.2703 (3)	0.49981 (17)	0.2138 (3)	0.0112 (4)
H1	0.3340	0.5647	0.2786	0.013*
C5	0.1772 (3)	0.50202 (18)	0.5231 (3)	0.0144 (5)
H5	0.2957	0.5025	0.5382	0.017*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0110 (2)	0.0136 (2)	0.0095 (2)	0.00028 (12)	0.00592 (16)	−0.00072 (12)
O2	0.0258 (8)	0.0209 (8)	0.0175 (8)	0.0000 (7)	0.0058 (6)	0.0008 (6)
O1	0.0144 (7)	0.0196 (8)	0.0142 (7)	0.0003 (6)	0.0073 (6)	−0.0034 (6)
N2	0.0118 (8)	0.0144 (9)	0.0107 (8)	0.0009 (7)	0.0063 (7)	0.0008 (7)
N1	0.0144 (8)	0.0131 (8)	0.0123 (8)	0.0014 (7)	0.0062 (7)	0.0000 (7)
C7	0.0202 (10)	0.0138 (10)	0.0205 (11)	−0.0035 (8)	0.0124 (9)	−0.0034 (9)
C4	0.0158 (10)	0.0131 (9)	0.0104 (9)	0.0010 (8)	0.0077 (8)	0.0029 (8)
C3	0.0139 (9)	0.0150 (10)	0.0140 (9)	−0.0027 (8)	0.0045 (8)	−0.0008 (8)
C2	0.0181 (10)	0.0150 (10)	0.0117 (9)	−0.0005 (8)	0.0059 (8)	−0.0030 (8)
C6	0.0128 (10)	0.0216 (10)	0.0080 (9)	−0.0016 (8)	0.0028 (8)	−0.0006 (8)
C1	0.0115 (11)	0.0137 (10)	0.0098 (10)	0.0003 (7)	0.0050 (9)	0.0012 (7)
C5	0.0101 (10)	0.0201 (12)	0.0143 (11)	−0.0004 (7)	0.0055 (9)	0.0014 (7)

Geometric parameters (Å, º) top

Cu1—O1ⁱ	1.9485 (14)	C7—H7	0.9300
Cu1—O1	1.9485 (14)	C4—C5	1.384 (3)
Cu1—N1ⁱ	1.9953 (17)	C4—C6	1.384 (3)
Cu1—N1	1.9953 (17)	C3—C2	1.350 (3)
O2—C7	1.235 (3)	C3—H3	0.9300
O1—C7	1.267 (3)	C2—H2	0.9300
N2—C1	1.351 (3)	C6—C5ⁱⁱ	1.390 (3)
N2—C3	1.382 (3)	C6—H6	0.9300
N2—C4	1.433 (3)	C1—H1	0.9300
N1—C1	1.329 (3)	C5—C6ⁱⁱ	1.390 (3)
N1—C2	1.381 (3)	C5—H5	0.9300

O1ⁱ—Cu1—O1	180.00 (8)	C5—C4—N2	119.09 (19)
O1ⁱ—Cu1—N1ⁱ	89.73 (7)	C6—C4—N2	119.75 (19)
O1—Cu1—N1ⁱ	90.27 (7)	C2—C3—N2	105.86 (17)
O1ⁱ—Cu1—N1	90.27 (7)	C2—C3—H3	127.1
O1—Cu1—N1	89.73 (7)	N2—C3—H3	127.1
N1ⁱ—Cu1—N1	180.0	C3—C2—N1	109.86 (17)
C7—O1—Cu1	107.51 (12)	C3—C2—H2	125.1
C1—N2—C3	107.92 (16)	N1—C2—H2	125.1
C1—N2—C4	124.60 (17)	C4—C6—C5ⁱⁱ	119.3 (2)
C3—N2—C4	127.48 (17)	C4—C6—H6	120.4
C1—N1—C2	106.15 (17)	C5ⁱⁱ—C6—H6	120.4
C1—N1—Cu1	125.33 (14)	N1—C1—N2	110.19 (18)
C2—N1—Cu1	128.41 (13)	N1—C1—H1	124.9
O2—C7—O1	126.19 (19)	N2—C1—H1	124.9
O2—C7—H7	116.9	C4—C5—C6ⁱⁱ	119.6 (2)
O1—C7—H7	116.9	C4—C5—H5	120.2
C5—C4—C6	121.1 (2)	C6ⁱⁱ—C5—H5	120.2

O1ⁱ—Cu1—O1—C7	−151.1 (3)	C1—N2—C3—C2	1.1 (2)
N1ⁱ—Cu1—O1—C7	93.37 (13)	C4—N2—C3—C2	−179.90 (19)
N1—Cu1—O1—C7	−86.63 (13)	N2—C3—C2—N1	−0.7 (2)
O1ⁱ—Cu1—N1—C1	168.60 (17)	C1—N1—C2—C3	0.1 (2)
O1—Cu1—N1—C1	−11.40 (17)	Cu1—N1—C2—C3	176.50 (14)
N1ⁱ—Cu1—N1—C1	−7 (100)	C5—C4—C6—C5ⁱⁱ	1.2 (3)
O1ⁱ—Cu1—N1—C2	−7.16 (17)	N2—C4—C6—C5ⁱⁱ	−177.73 (18)
O1—Cu1—N1—C2	172.84 (17)	C2—N1—C1—N2	0.6 (2)
N1ⁱ—Cu1—N1—C2	177 (100)	Cu1—N1—C1—N2	−175.95 (12)
Cu1—O1—C7—O2	−2.2 (3)	C3—N2—C1—N1	−1.1 (2)
C1—N2—C4—C5	−35.7 (3)	C4—N2—C1—N1	179.88 (17)
C3—N2—C4—C5	145.4 (2)	C6—C4—C5—C6ⁱⁱ	−1.2 (3)
C1—N2—C4—C6	143.3 (2)	N2—C4—C5—C6ⁱⁱ	177.73 (18)
C3—N2—C4—C6	−35.6 (3)

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

Experimental details

Crystal data
Chemical formula	[Cu(CHO₂)₂(C₁₂H₁₀N₄)]
M_r	363.82
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.0971 (16), 10.426 (2), 8.5723 (17)
β (°)	107.02 (3)
V (Å³)	692.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.61
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku Mercury CCD area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.624, 0.725
No. of measured, independent and observed [I > 2σ(I)] reflections	6003, 1204, 1108
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.075, 1.11
No. of reflections	1204
No. of parameters	106
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.39

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

Cui, G. H., Li, J. R., Tian, J. L., Bu, X. H. & Batten, S. R. (2005). Cryst. Growth Des. 5, 1775–1780. Web of Science CSD CrossRef CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Jin, C. M., Wu, L. Y., Lu, H. & Xu, Y. (2008). Cryst. Growth Des. 8, 215–218. Web of Science CSD CrossRef CAS Google Scholar
Li, Z. X., Xu, Y., Zuo, Y., Li, L., Pan, Q., Hu, T. L. & Bu, X. H. (2009). Cryst. Growth Des. 9, 3904–3909. Web of Science CSD CrossRef CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar