Poly[{μ3-3-[4-(1H-imidazol-1-yl­methyl)phen­yl]prop-2-enoato-κN:η2:κO}copper(I)]

Lou, B.

doi:10.1107/S1600536811015005

metal-organic compounds

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Volume 67| Part 5| May 2011| Page m640

doi:10.1107/S1600536811015005

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Poly[{μ₃-3-[4-(1H-imidazol-1-ylmethyl)phenyl]prop-2-enoato-κN:η²:κO}copper(I)]

Benyong Lou ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Minjiang University, Fuzhou 350108, People's Republic of China
^*Correspondence e-mail: lby@mju.edu.cn

(Received 19 April 2011; accepted 21 April 2011; online 29 April 2011)

In the coordination polymer, [Cu^I(C₁₃H₁₁N₂O₂)]_n, the Cu^I atom exists in a trigonal–planar geometry that is defined by the C=C unit, the imidazole N atom and carboxylate O atoms from three different ozagrel ligands, resulting in the formation of a three-dimensional framework.

Related literature

For background to the design and construction of coordination polymers, see: Kitagawa et al. (2004 ); Zhao et al. (2008 ). For other olefin complexes, see: Kato et al. (1997 ); Wang et al. (2005 , 2007 ); Young et al. (1998 ); Zhang et al. (2001 ).

Experimental

Crystal data

[Cu(C₁₃H₁₁N₂O₂)]
M_r = 290.78
Trigonal, P 3₁
a = 9.7894 (19) Å
c = 10.483 (2) Å
V = 870.0 (3) Å³
Z = 3
Mo Kα radiation
μ = 1.88 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 ) T_min = 0.765, T_max = 1.000
6852 measured reflections
2105 independent reflections
1904 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.105
S = 1.03
2105 reflections
163 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ), 773 Friedel pairs
Flack parameter: 0.05 (3)

Table 1
Selected geometric parameters (Å, °)

Cu1—N1ⁱ	1.962 (5)
Cu1—C2	2.000 (6)
Cu1—O2ⁱⁱ	2.007 (4)
Cu1—C3	2.030 (5)
C2—C3	1.381 (7)

N1ⁱ—Cu1—C2	151.2 (2)
N1ⁱ—Cu1—O2ⁱⁱ	104.12 (19)
C2—Cu1—O2ⁱⁱ	104.49 (19)
N1ⁱ—Cu1—C3	111.1 (2)
C2—Cu1—C3	40.1 (2)
Symmetry codes: (i) $[-x+y, -x, z+{\script{2\over 3}}]$ ; (ii) $[-y+1, x-y, z+{\script{1\over 3}}]$ .

Data collection: CrystalClear (Rigaku, 2000); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015005/ng5155sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015005/ng5155Isup2.hkl

checkCIF report

Comment top

The design and construction of coordination polymers have been an area of explosive growth in recent years (Kitagawa et al., 2004). Some active pharmaceutical ingredients (APIs), which contain carboxylic group, N-containing ring in the structures, have also utilized for constructing specific functional coordination polymers (Zhao et al., 2008). The hydrophilic or hydrophobic groups in drug molecules may play an important role in the structures and properties of final metal- organic frameworks.

Ozagrel, (E)-3-[4-(1H-imidiazol-1-ylmethyl)phenyl]-2-propenic acid, is a selective thromboxane A2-synthetase inhibitor which is used for treating cerebrovascular disease (Kato et al., 1997). It has a carboxylic group and an imidazole ring in the structure. The molecule is an ideal building block for constructing coordination polymers with specific structures. In this contribution, we report a Cu(I)-olefin coordination polymer of ozagrel, [(C₁₃H₁₁N₂O₂)Cu(I)] (I), which was obtained under solvothermal reaction conditions. In the structure, conjugated olefinic and carboxylic groups of ozagrel link metal centers into a 3-fold helical chain which is linked into a three-dimensional framework structure by metal- imidazole coordination interactions.

Compound I crystallizes in the space group P31 with a deprotonated ozagrel anion and a Cu(I) cation in the asymmetric unit (Fig.1). There exist obvious interactions between Cu(I) center and C═C moiety of the olefin of ozagrel (Cu1—C2, Cu1—C3, Table 1). The C═C bond distance (1.381 Å) of the coordinated olefin is longer than that in free ozagrel (1.324 Å) (Wang et al., 2007). The lengthening of the C═C distance is typical for ethylene that is η²-bonded to low-valent, electron-rich, transition metals such as copper(I) (Young et al., 1998). Cu(I) ion is nearly centered in a trigonal planar geometry, which is defined by C═C moiety, imidazole N atom and carboxylic O atom from three different ozagrel molecules. Interestingly, carboxylic group of ozagrel doesn't serve as bidentate moiety as does it in [Cu(3-PYA)]n reported previously (Zhang et al., 2001). But, conjugated olefinic and carboxylic groups as bidentate spacer link Cu(I) centers into a 3-fold helical chain along c axis (Fig.2). Cu(I)-imidazole interactions further link the one-dimensional helical chain into a three-dimensional framework structure (Fig.3). Thus, ozagrel anion acting as a tridentate linker is coordinated to Cu(I) ion generating a three-dimensional coordination polymer based on one-dimensional helical chain of Cu(I) centers.

Since Schultz synthesized the first air-stable Cu(I)-olefin coordination polymer based on fumarate ligand under hydrothermal conditions (Young et al., 1998), some Cu(I)-olefin complexes with extended framework structures have been prepared by crystal engineering strategies (Wang et al., 2005). Impressively, two luminescent two-dimensional layered copper(I)-olefin coordination polymers were constructed by the use of 3(2)-pyridylacrylic acid as tetradentate linkers (Zhang et al., 2001). Therein, acrylic acid anions linked Cu(I) centers into a one-dimensional chain which was further linked into two-dimensional coordination layers by coordinated pyridyl rings. Otherwise from that in pyridylacrylic acid, the acrylic acid anion in ozagrel acts as a bidentate spacer and links Cu(I) centers into a 3-fold helical chain which is further linked into a three-dimensional framework structure by coordinated imidazole ring. In other words, rigid 3(2)-pyridylacrylic acid resulted in two-dimensional coordination layers by metal coordination to Cu(I) ion while more flexible ozagrel gave rise to a three-dimensional coordination framework. The flexible molecular structure of ozagrel could play the subtle role in the final extended structure.

In conclusion, a Cu(I)-olefin coordination polymer based on ozagrel ligand was synthesized under solvothermal conditions. Conjugated olefinic and carboxylic groups of ozagrel as bidentate spacer link Cu(I) centers into a 3-fold helical chain which is linked into a three-dimensional framework structure by metal-imidazole coordination interactions.

Related literature top

For background, see: Kitagawa et al. (2004); Zhao et al. (2008). For other olefin complexes, see: Kato et al. (1997); Wang et al. (2005, 2007); Young et al. (1998); Zhang et al. (2001).

Experimental top

Ozagrel (228 mg, 1 mmol) and Cu(NO₃)₂.3H₂O (240 mg, 1 mmol) were suspended in 10 ml me thanol and a few drops of triethylamine were added. The mixture was placed in a 23 ml Teflon-lined autoclave, sealed, and placed in a furnace at 130 °C for 2 days. Yellow block crystals were isolated. Element analysis for C₁₃H₁₁N₂O₂ Cu₁ (%), Calcd: C, 53.65; H, 3.22; N, 9.63; Found: C, 53.57; H, 3.89; N, 9.66.

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear (Rigaku, 2000); data reduction: CrystalClear (Rigaku, 2000); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP of compound I with 30% thermal ellipsoids. A = 1-Y,X—Y,Z+1/3; B = –X+Y,-X,Z+2/3
	Fig. 2. One-dimensional helical chain of Cu(I) along c axis in compound I. Imidazole group of ozagrel is omitted for clarity.
	Fig. 3. The three-dimensional structure of compound I viewed along c axis.

Poly[{µ₃-3-[4-(1H-imidazol-1-ylmethyl)phenyl]prop-2-enoato- κN:η²:κO}copper(I)] top

Crystal data top

[Cu(C₁₃H₁₁N₂O₂)]	D_x = 1.665 Mg m⁻³
M_r = 290.78	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3₁	Cell parameters from 987 reflections
Hall symbol: P 31	θ = 2.4–27.4°
a = 9.7894 (19) Å	µ = 1.88 mm⁻¹
c = 10.483 (2) Å	T = 293 K
V = 870.0 (3) Å³	Block, yellow
Z = 3	0.20 × 0.20 × 0.20 mm
F(000) = 444

Data collection top

Rigaku Mercury CCD diffractometer	2105 independent reflections
Radiation source: fine-focus sealed tube	1904 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
ϕ and ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	k = −12→12
T_min = 0.765, T_max = 1.000	l = −9→13
6852 measured reflections

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.052P)² + 0.5211P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2105 reflections	Δρ_max = 0.36 e Å⁻³
163 parameters	Δρ_min = −0.32 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 773 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (3)

Crystal data top

[Cu(C₁₃H₁₁N₂O₂)]	Z = 3
M_r = 290.78	Mo Kα radiation
Trigonal, P3₁	µ = 1.88 mm⁻¹
a = 9.7894 (19) Å	T = 293 K
c = 10.483 (2) Å	0.20 × 0.20 × 0.20 mm
V = 870.0 (3) Å³

Data collection top

Rigaku Mercury CCD diffractometer	2105 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	1904 reflections with I > 2σ(I)
T_min = 0.765, T_max = 1.000	R_int = 0.053
6852 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.105	Δρ_max = 0.36 e Å⁻³
S = 1.03	Δρ_min = −0.32 e Å⁻³
2105 reflections	Absolute structure: Flack (1983), 773 Friedel pairs
163 parameters	Absolute structure parameter: 0.05 (3)
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
Cu1	0.44797 (7)	0.33783 (7)	0.62232 (6)	0.03118 (17)
O1	0.6474 (5)	0.5593 (5)	0.3892 (5)	0.0532 (12)
N1	−0.3953 (6)	−0.0278 (5)	0.1055 (5)	0.0353 (11)
C1	0.6055 (6)	0.4173 (6)	0.3901 (5)	0.0335 (11)
O2	0.6941 (4)	0.3626 (5)	0.3546 (4)	0.0413 (9)
N2	−0.3899 (5)	−0.0886 (6)	0.3067 (5)	0.0375 (10)
C2	0.4448 (6)	0.2963 (6)	0.4352 (5)	0.0312 (11)
H2	0.4069	0.1847	0.4093	0.037*
C3	0.3305 (6)	0.3354 (6)	0.4620 (5)	0.0330 (12)
H3	0.3597	0.4436	0.4320	0.040*
C4	0.1578 (6)	0.2269 (6)	0.4662 (5)	0.0311 (11)
C5	0.0875 (7)	0.0622 (7)	0.4627 (6)	0.0403 (13)
H5	0.1519	0.0150	0.4631	0.048*
C6	−0.0749 (7)	−0.0321 (7)	0.4588 (6)	0.0406 (13)
H6	−0.1213	−0.1436	0.4558	0.049*
C7	0.0604 (6)	0.2919 (7)	0.4678 (6)	0.0387 (13)
H7	0.1061	0.4034	0.4692	0.046*
C8	−0.1017 (7)	0.1980 (7)	0.4675 (6)	0.0417 (14)
H8	−0.1662	0.2449	0.4731	0.050*
C9	−0.1707 (6)	0.0355 (7)	0.4591 (6)	0.0357 (12)
C10	−0.3482 (7)	−0.0695 (9)	0.4438 (6)	0.0441 (15)
H10A	−0.3824	−0.1740	0.4824	0.053*
H10B	−0.4031	−0.0216	0.4884	0.053*
C11	−0.3627 (7)	0.0271 (7)	0.2233 (6)	0.0403 (13)
H11	−0.3250	0.1340	0.2462	0.048*
C12	−0.4460 (7)	−0.2242 (7)	0.2378 (6)	0.0449 (14)
H12	−0.4761	−0.3261	0.2701	0.054*
C13	−0.4504 (7)	−0.1860 (7)	0.1143 (6)	0.0392 (13)
H13	−0.4863	−0.2579	0.0448	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0309 (3)	0.0364 (4)	0.0284 (3)	0.0185 (3)	0.0010 (3)	0.0030 (3)
O1	0.038 (2)	0.035 (2)	0.082 (4)	0.0155 (18)	0.004 (2)	0.012 (2)
N1	0.041 (3)	0.030 (2)	0.036 (3)	0.019 (2)	−0.003 (2)	0.002 (2)
C1	0.029 (2)	0.043 (3)	0.029 (3)	0.018 (2)	0.002 (2)	0.005 (2)
O2	0.037 (2)	0.044 (2)	0.043 (2)	0.0197 (17)	0.0039 (17)	0.0035 (18)
N2	0.030 (2)	0.044 (3)	0.035 (3)	0.016 (2)	−0.0026 (19)	0.006 (2)
C2	0.030 (3)	0.029 (2)	0.030 (3)	0.011 (2)	0.002 (2)	0.003 (2)
C3	0.031 (3)	0.041 (3)	0.030 (3)	0.021 (2)	−0.005 (2)	0.005 (2)
C4	0.032 (3)	0.033 (3)	0.028 (3)	0.016 (2)	−0.002 (2)	0.005 (2)
C5	0.041 (3)	0.047 (3)	0.043 (3)	0.030 (3)	−0.002 (3)	0.005 (3)
C6	0.036 (3)	0.036 (3)	0.042 (3)	0.012 (2)	−0.001 (2)	0.002 (2)
C7	0.029 (3)	0.031 (3)	0.052 (4)	0.011 (2)	−0.006 (2)	−0.003 (3)
C8	0.036 (3)	0.051 (3)	0.048 (4)	0.029 (3)	−0.007 (3)	0.001 (3)
C9	0.031 (3)	0.041 (3)	0.027 (3)	0.013 (2)	0.000 (2)	0.005 (2)
C10	0.030 (3)	0.054 (4)	0.036 (3)	0.012 (3)	0.001 (2)	0.008 (3)
C11	0.041 (3)	0.037 (3)	0.037 (3)	0.015 (2)	−0.002 (2)	0.004 (2)
C12	0.050 (3)	0.038 (3)	0.048 (4)	0.023 (3)	−0.002 (3)	0.000 (3)
C13	0.047 (3)	0.031 (3)	0.041 (3)	0.021 (3)	−0.003 (3)	−0.003 (2)

Geometric parameters (Å, º) top

Cu1—N1ⁱ	1.962 (5)	C4—C7	1.386 (8)
Cu1—C2	2.000 (6)	C4—C5	1.402 (8)
Cu1—O2ⁱⁱ	2.007 (4)	C5—C6	1.383 (8)
Cu1—C3	2.030 (5)	C5—H5	0.9500
O1—C1	1.237 (7)	C6—C9	1.392 (8)
N1—C11	1.320 (8)	C6—H6	0.9500
N1—C13	1.364 (7)	C7—C8	1.380 (7)
N1—Cu1ⁱⁱⁱ	1.962 (5)	C7—H7	0.9500
C1—O2	1.281 (6)	C8—C9	1.386 (8)
C1—C2	1.496 (7)	C8—H8	0.9500
O2—Cu1^iv	2.007 (4)	C9—C10	1.521 (8)
N2—C11	1.347 (7)	C10—H10A	0.9900
N2—C12	1.363 (8)	C10—H10B	0.9900
N2—C10	1.480 (8)	C11—H11	0.9500
C2—C3	1.381 (7)	C12—C13	1.354 (9)
C2—H2	1.0000	C12—H12	0.9500
C3—C4	1.481 (7)	C13—H13	0.9500
C3—H3	1.0000

N1ⁱ—Cu1—C2	151.2 (2)	C6—C5—C4	120.5 (5)
N1ⁱ—Cu1—O2ⁱⁱ	104.12 (19)	C6—C5—H5	119.7
C2—Cu1—O2ⁱⁱ	104.49 (19)	C4—C5—H5	119.7
N1ⁱ—Cu1—C3	111.1 (2)	C5—C6—C9	120.3 (5)
C2—Cu1—C3	40.1 (2)	C5—C6—H6	119.8
O2ⁱⁱ—Cu1—C3	144.1 (2)	C9—C6—H6	119.8
C11—N1—C13	106.1 (5)	C8—C7—C4	121.3 (5)
C11—N1—Cu1ⁱⁱⁱ	122.7 (4)	C8—C7—H7	119.3
C13—N1—Cu1ⁱⁱⁱ	130.5 (4)	C4—C7—H7	119.3
O1—C1—O2	123.6 (5)	C7—C8—C9	120.2 (5)
O1—C1—C2	121.2 (5)	C7—C8—H8	119.9
O2—C1—C2	115.2 (5)	C9—C8—H8	119.9
C1—O2—Cu1^iv	104.3 (3)	C8—C9—C6	119.2 (5)
C11—N2—C12	106.8 (5)	C8—C9—C10	121.3 (5)
C11—N2—C10	126.7 (5)	C6—C9—C10	119.5 (5)
C12—N2—C10	126.1 (5)	N2—C10—C9	109.7 (5)
C3—C2—C1	121.5 (5)	N2—C10—H10A	109.7
C3—C2—Cu1	71.1 (3)	C9—C10—H10A	109.7
C1—C2—Cu1	104.2 (3)	N2—C10—H10B	109.7
C3—C2—H2	116.6	C9—C10—H10B	109.7
C1—C2—H2	116.6	H10A—C10—H10B	108.2
Cu1—C2—H2	116.6	N1—C11—N2	111.0 (5)
C2—C3—C4	126.9 (5)	N1—C11—H11	124.5
C2—C3—Cu1	68.8 (3)	N2—C11—H11	124.5
C4—C3—Cu1	114.9 (4)	C13—C12—N2	106.9 (5)
C2—C3—H3	112.8	C13—C12—H12	126.6
C4—C3—H3	112.8	N2—C12—H12	126.6
Cu1—C3—H3	112.8	C12—C13—N1	109.2 (5)
C7—C4—C5	118.2 (5)	C12—C13—H13	125.4
C7—C4—C3	118.2 (5)	N1—C13—H13	125.4
C5—C4—C3	123.5 (5)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₁₃H₁₁N₂O₂)]
M_r	290.78
Crystal system, space group	Trigonal, P3₁
Temperature (K)	293
a, c (Å)	9.7894 (19), 10.483 (2)
V (Å³)	870.0 (3)
Z	3
Radiation type	Mo Kα
µ (mm⁻¹)	1.88
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2000)
T_min, T_max	0.765, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6852, 2105, 1904
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.105, 1.03
No. of reflections	2105
No. of parameters	163
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.32
Absolute structure	Flack (1983), 773 Friedel pairs
Absolute structure parameter	0.05 (3)

Computer programs: CrystalClear (Rigaku, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu1—N1ⁱ	1.962 (5)	Cu1—C3	2.030 (5)
Cu1—C2	2.000 (6)	C2—C3	1.381 (7)
Cu1—O2ⁱⁱ	2.007 (4)

N1ⁱ—Cu1—C2	151.2 (2)	N1ⁱ—Cu1—C3	111.1 (2)
N1ⁱ—Cu1—O2ⁱⁱ	104.12 (19)	C2—Cu1—C3	40.1 (2)
C2—Cu1—O2ⁱⁱ	104.49 (19)

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

Acknowledgements

The author is grateful for grants from the National Natural Science Foundation of China (grant No. 20901037), Fujian Provincial Department of Education (grant No. JB09181) and the Program for New Century Excellent Talents in Fujian Province University (grant No. JK2010043).

References

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