catena-Poly[[bis­(1-vinyl­imidazole-κN³)zinc(II)]-μ-phthalato-κ²O¹:O²]

The title compound, [Zn(C₈H₄O₄)(C₅H₆N₂)₂]_n, in the solid state comprises polymeric zigzag chains extending along the c axis. Each Zn^II ion is coordinated by two N [Zn—N = 1.991 (6) and 2.031 (5) Å] and two O [Zn—O = 1.912 (5) and 1.965 (5) Å] atoms in a distorted tetra­hedral geometry. Weak C—H...O inter­actions contribute to the crystal packing stability.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.045
• wR factor = 0.139
• Data-to-parameter ratio = 19.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         12

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn          (2)       1.98
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        133

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

In the title compound, (I) (Fig. 1), the zinc(II) centers are bridged by the carboxylate group of o-phthalate and saturated by 1-vinylimidazole. Each Zn^II ion is coordinated by two N [Zn—N1 = 1.993 (3) Å, Zn—N3 = 2.031 (5) Å] and two O [Zn—O2 = 1.912 (5) Å, Zn—O3 = 1.965 (5) Å] atoms in a distorted tetrahedral geometry. All these values agree well with those observed in [Zn(phthalato)(1-H-imidazole)₂] (Liu et al., 2002), where Zn^II ions also have a distorted tetrahedral environment. Each o-phthalate in (I) dianion acts as a bidentate ligand to bridge two Zn^II ions through the two monodentate carboxylate groups, building a zigzag infinate chain structure along the c axis. The metal-metal distances across each polymer backbone are 7.1397 (18) Å.

In the crystal, weak C—H···O interactions (Table 1) contribute to the crystal packing stability.

Related literature

In the corresponding compound [Zn(phthalato)(1-H-imidazole)₂] the Zn^II ions have a distorted tetrahedral environment (Liu et al., 2002).

S2. Experimental

The reaction of ZnCl₂ (0.68 g, 5 mmol) with o-phthalic acid (0.83 g, 5 mmol) in an aqueous-alcohol (3:1) solution (40 ml) at 363 K for 30 minutes produced a blue solution, to which 1-vinylimidazole (0.94 g, 10 mmol) was added. The reaction solution was kept at room temperature after stirring for an hour at 333 K. Colourless crystals were obtained after a few days.

S3. Refinement

All H atoms were positioned geometrically (C—H 0.93 Å) and allowed to ride on their parent atoms with U_iso(H) = 1.2 U_eq(C).

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2001) and local programs.

Figures

	Fig. 1. A portion of the polymeric chain in the title compound showing the atomic numbering and 30% probability displacement ellipsoids [symmetry code: (A) x,-y + 1/2,z + 1/2].
	Fig. 2. The packing of (I), viewed down the b axis.

catena-Poly[[bis(1-vinylimidazole-κN³)zinc(II)]-µ-phthalato-κ²O¹:O²]

Crystal data

[Zn(C8H4O4)(C5H6N2)2]	F(000) = 856
Mr = 417.72	Dx = 1.461 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3025 reflections
a = 8.4110 (17) Å	θ = 2.5–25.1°
b = 16.329 (3) Å	µ = 1.32 mm^−1
c = 14.083 (3) Å	T = 293 K
β = 100.87 (3)°	Block, colourless
V = 1899.5 (7) Å^3	0.40 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART 1K CCD area-detector diffractometer	3678 independent reflections
Radiation source: fine-focus sealed tube	2090 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
thin–slice ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
Tmin = 0.620, Tmax = 0.879	k = 0→20
3729 measured reflections	l = 0→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.1041P)^2] where P = (Fo^2 + 2Fc^2)/3
3678 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 1.03 e Å^−3
133 restraints	Δρmin = −1.09 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Zn	0.11543 (10)	0.21386 (5)	0.54220 (5)	0.0456 (3)
O1	0.0879 (6)	0.1714 (3)	0.2024 (3)	0.0524 (12)
O2	0.2671 (6)	0.2117 (3)	0.1147 (3)	0.0608 (14)
O3	0.2286 (6)	0.1414 (3)	0.4655 (3)	0.0570 (14)
O4	0.2799 (7)	0.2508 (3)	0.3833 (3)	0.0567 (14)
N1	−0.0828 (8)	0.2607 (4)	0.4605 (4)	0.0562 (16)
N2	−0.2745 (10)	0.2885 (5)	0.3388 (6)	0.087 (2)
N3	0.0464 (7)	0.1306 (3)	0.6335 (4)	0.0459 (13)
N4	0.0425 (8)	0.0561 (4)	0.7615 (5)	0.059
C1	0.5666 (14)	0.0239 (7)	0.2496 (8)	0.105
H1A	0.6262	−0.0093	0.2156	0.125*
C2	0.4515 (10)	0.0729 (5)	0.1993 (6)	0.068 (2)
H2A	0.4353	0.0730	0.1322	0.082*
C3	0.3591 (8)	0.1219 (4)	0.2441 (4)	0.0469 (16)
C4	0.3852 (8)	0.1234 (4)	0.3456 (5)	0.0452 (16)
C5	0.5051 (10)	0.0725 (5)	0.3981 (6)	0.064 (2)
H5A	0.5227	0.0727	0.4653	0.077*
C6	0.5999 (12)	0.0208 (6)	0.3497 (7)	0.087 (3)
H6A	0.6798	−0.0132	0.3834	0.104*
C7	0.2259 (8)	0.1715 (4)	0.1859 (4)	0.0422 (16)
C8	0.2909 (8)	0.1767 (5)	0.3999 (5)	0.0439 (16)
C9	−0.1283 (10)	0.2505 (5)	0.3651 (6)	0.067 (2)
H9A	−0.0713	0.2229	0.3245	0.080*
C10	−0.3184 (13)	0.3235 (7)	0.4126 (7)	0.089
H10A	−0.4129	0.3530	0.4128	0.107*
C11	−0.1980 (14)	0.3083 (7)	0.4892 (8)	0.099
H11A	−0.1946	0.3275	0.5517	0.119*
C12	−0.3286 (13)	0.2862 (6)	0.2280 (8)	0.101
H12A	−0.2862	0.2467	0.1922	0.121*
C13	−0.4307 (12)	0.3378 (7)	0.1850 (8)	0.101
H13A	−0.4734	0.3774	0.2205	0.121*
H13B	−0.4625	0.3359	0.1181	0.121*
C14	0.0926 (8)	0.1266 (4)	0.7271 (5)	0.0464 (16)
H14A	0.1520	0.1669	0.7649	0.056*
C15	−0.0419 (11)	0.0139 (6)	0.6833 (6)	0.080
H15A	−0.0898	−0.0373	0.6848	0.097*
C16	−0.0421 (10)	0.0598 (5)	0.6052 (6)	0.064
H16A	−0.0927	0.0468	0.5425	0.077*
C17	0.0665 (12)	0.0246 (7)	0.8540 (7)	0.087
H17A	0.0191	−0.0257	0.8626	0.105*
C18	0.1471 (12)	0.0584 (6)	0.9271 (7)	0.090 (3)
H18A	0.1964	0.1087	0.9214	0.108*
H18B	0.1579	0.0333	0.9873	0.108*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn	0.0559 (5)	0.0507 (5)	0.0273 (4)	0.0043 (4)	0.0006 (3)	−0.0008 (4)
O1	0.057 (3)	0.051 (3)	0.048 (3)	0.003 (3)	0.007 (2)	0.011 (2)
O2	0.068 (3)	0.073 (4)	0.041 (3)	0.007 (3)	0.008 (2)	0.016 (3)
O3	0.086 (4)	0.054 (3)	0.035 (3)	0.009 (3)	0.020 (3)	0.005 (2)
O4	0.085 (4)	0.044 (3)	0.040 (3)	0.016 (3)	0.010 (3)	−0.003 (2)
N1	0.061 (4)	0.063 (4)	0.041 (3)	−0.003 (3)	0.001 (3)	0.004 (3)
N2	0.079 (5)	0.084 (5)	0.080 (4)	0.001 (4)	−0.031 (4)	0.010 (4)
N3	0.055 (3)	0.047 (3)	0.037 (3)	0.006 (3)	0.009 (3)	−0.002 (2)
N4	0.059	0.059	0.059	0.000	0.011	0.000
C1	0.105	0.105	0.105	0.000	0.020	0.000
C2	0.092 (6)	0.069 (5)	0.048 (4)	0.016 (4)	0.022 (4)	0.004 (4)
C3	0.056 (4)	0.052 (4)	0.032 (3)	−0.002 (3)	0.005 (3)	0.001 (3)
C4	0.056 (4)	0.045 (4)	0.034 (3)	0.000 (3)	0.006 (3)	0.007 (3)
C5	0.074 (5)	0.062 (5)	0.052 (4)	0.018 (4)	0.001 (4)	0.014 (3)
C6	0.077 (6)	0.098 (6)	0.084 (5)	0.031 (5)	0.013 (4)	0.008 (5)
C7	0.051 (4)	0.040 (4)	0.031 (3)	−0.001 (3)	−0.002 (3)	−0.001 (3)
C8	0.043 (4)	0.050 (4)	0.031 (3)	0.001 (3)	−0.010 (3)	−0.004 (3)
C9	0.063 (4)	0.074 (5)	0.059 (4)	−0.014 (4)	−0.001 (4)	0.009 (4)
C10	0.089	0.089	0.089	0.000	0.017	0.000
C11	0.099	0.099	0.099	0.000	0.019	0.000
C12	0.101	0.101	0.101	0.000	0.019	0.000
C13	0.101	0.101	0.101	0.000	0.019	0.000
C14	0.061 (4)	0.042 (3)	0.037 (3)	0.006 (3)	0.012 (3)	0.002 (3)
C15	0.080	0.080	0.080	0.000	0.015	0.000
C16	0.064	0.064	0.064	0.000	0.012	0.000
C17	0.087	0.087	0.087	0.000	0.016	0.000
C18	0.103 (8)	0.082 (7)	0.082 (7)	0.005 (6)	0.009 (6)	0.010 (6)

Geometric parameters (Å, º)

Zn—O2^i	1.912 (5)	C3—C4	1.406 (8)
Zn—O3	1.965 (5)	C3—C7	1.495 (7)
Zn—N1	1.991 (6)	C4—C5	1.404 (9)
Zn—N3	2.031 (5)	C4—C8	1.483 (9)
O1—C7	1.226 (8)	C5—C6	1.420 (11)
O2—C7	1.299 (8)	C5—H5A	0.9300
O2—Zn^ii	1.912 (5)	C6—H6A	0.9300
O3—C8	1.282 (8)	C9—H9A	0.9300
O4—C8	1.232 (8)	C10—C11	1.356 (14)
N1—C9	1.335 (9)	C10—H10A	0.9300
N1—C11	1.363 (12)	C11—H11A	0.9300
N2—C10	1.299 (12)	C12—C13	1.272 (8)
N2—C9	1.365 (11)	C12—H12A	0.9300
N2—C12	1.541 (12)	C13—H13A	0.9300
N3—C14	1.303 (8)	C13—H13B	0.9300
N3—C16	1.392 (9)	C14—H14A	0.9300
N4—C14	1.348 (9)	C15—C16	1.330 (11)
N4—C15	1.377 (10)	C15—H15A	0.9300
N4—C17	1.379 (10)	C16—H16A	0.9300
C1—C2	1.350 (13)	C17—C18	1.250 (12)
C1—C6	1.385 (12)	C17—H17A	0.9300
C1—H1A	0.9300	C18—H18A	0.9300
C2—C3	1.351 (10)	C18—H18B	0.9300
C2—H2A	0.9300
O2^i—Zn—O3	109.4 (2)	C5—C6—H6A	121.8
O2^i—Zn—N1	117.8 (3)	O1—C7—O2	123.2 (6)
O3—Zn—N1	110.7 (2)	O1—C7—C3	122.2 (6)
O2^i—Zn—N3	109.3 (2)	O2—C7—C3	114.6 (6)
O3—Zn—N3	99.9 (2)	O4—C8—O3	123.5 (7)
N1—Zn—N3	108.4 (2)	O4—C8—C4	120.5 (6)
C7—O2—Zn^ii	119.0 (4)	O3—C8—C4	116.0 (6)
C8—O3—Zn	115.6 (4)	N1—C9—N2	106.8 (8)
C9—N1—C11	106.5 (8)	N1—C9—H9A	126.6
C9—N1—Zn	125.7 (6)	N2—C9—H9A	126.6
C11—N1—Zn	127.8 (6)	N2—C10—C11	105.9 (10)
C10—N2—C9	111.1 (8)	N2—C10—H10A	127.0
C10—N2—C12	138.3 (9)	C11—C10—H10A	127.0
C9—N2—C12	110.1 (9)	C10—C11—N1	109.5 (10)
C14—N3—C16	106.9 (6)	C10—C11—H11A	125.3
C14—N3—Zn	127.4 (5)	N1—C11—H11A	125.3
C16—N3—Zn	125.2 (5)	C13—C12—N2	120.6 (11)
C14—N4—C15	106.8 (7)	C13—C12—H12A	119.7
C14—N4—C17	131.2 (8)	N2—C12—H12A	119.7
C15—N4—C17	122.0 (8)	C12—C13—H13A	120.0
C2—C1—C6	122.9 (11)	C12—C13—H13B	120.0
C2—C1—H1A	118.6	H13A—C13—H13B	120.0
C6—C1—H1A	118.6	N3—C14—N4	110.6 (6)
C3—C2—C1	121.7 (8)	N3—C14—H14A	124.7
C3—C2—H2A	119.2	N4—C14—H14A	124.7
C1—C2—H2A	119.2	C16—C15—N4	107.5 (9)
C2—C3—C4	119.4 (6)	C16—C15—H15A	126.3
C2—C3—C7	120.1 (6)	N4—C15—H15A	126.3
C4—C3—C7	120.4 (6)	C15—C16—N3	108.3 (8)
C3—C4—C5	118.9 (7)	C15—C16—H16A	125.9
C3—C4—C8	122.5 (6)	N3—C16—H16A	125.9
C5—C4—C8	118.5 (6)	C18—C17—N4	124.9 (10)
C4—C5—C6	120.8 (7)	C18—C17—H17A	117.5
C4—C5—H5A	119.6	N4—C17—H17A	117.5
C6—C5—H5A	119.6	C17—C18—H18A	120.0
C1—C6—C5	116.3 (9)	C17—C18—H18B	120.0
C1—C6—H6A	121.8	H18A—C18—H18B	120.0
O2^i—Zn—O3—C8	−64.4 (5)	C2—C3—C7—O2	−47.7 (9)
N1—Zn—O3—C8	67.0 (5)	C4—C3—C7—O2	134.8 (7)
N3—Zn—O3—C8	−179.0 (5)	Zn—O3—C8—O4	−1.2 (9)
O2^i—Zn—N1—C9	121.9 (6)	Zn—O3—C8—C4	176.4 (4)
O3—Zn—N1—C9	−5.0 (7)	C3—C4—C8—O4	−52.7 (10)
N3—Zn—N1—C9	−113.5 (7)	C5—C4—C8—O4	127.3 (7)
O2^i—Zn—N1—C11	−58.4 (8)	C3—C4—C8—O3	129.7 (7)
O3—Zn—N1—C11	174.7 (7)	C5—C4—C8—O3	−50.4 (9)
N3—Zn—N1—C11	66.2 (8)	C11—N1—C9—N2	−3.2 (10)
O2^i—Zn—N3—C14	0.9 (6)	Zn—N1—C9—N2	176.6 (5)
O3—Zn—N3—C14	115.7 (6)	C10—N2—C9—N1	2.0 (11)
N1—Zn—N3—C14	−128.6 (6)	C12—N2—C9—N1	175.0 (7)
O2^i—Zn—N3—C16	−169.2 (5)	C9—N2—C10—C11	0.1 (12)
O3—Zn—N3—C16	−54.5 (6)	C12—N2—C10—C11	−169.9 (11)
N1—Zn—N3—C16	61.3 (6)	N2—C10—C11—N1	−2.1 (12)
C6—C1—C2—C3	−0.8 (13)	C9—N1—C11—C10	3.4 (11)
C1—C2—C3—C4	1.3 (10)	Zn—N1—C11—C10	−176.4 (6)
C1—C2—C3—C7	−176.2 (8)	C10—N2—C12—C13	12.3 (19)
C2—C3—C4—C5	−1.1 (10)	C9—N2—C12—C13	−157.8 (10)
C7—C3—C4—C5	176.3 (7)	C16—N3—C14—N4	1.4 (8)
C2—C3—C4—C8	178.8 (7)	Zn—N3—C14—N4	−170.2 (4)
C7—C3—C4—C8	−3.7 (10)	C15—N4—C14—N3	−0.5 (9)
C3—C4—C5—C6	0.5 (12)	C17—N4—C14—N3	177.9 (8)
C8—C4—C5—C6	−179.4 (8)	C14—N4—C15—C16	−0.8 (10)
C2—C1—C6—C5	0.2 (15)	C17—N4—C15—C16	−179.3 (8)
C4—C5—C6—C1	−0.1 (14)	N4—C15—C16—N3	1.6 (10)
Zn^ii—O2—C7—O1	8.7 (9)	C14—N3—C16—C15	−1.9 (9)
Zn^ii—O2—C7—C3	−173.8 (4)	Zn—N3—C16—C15	169.9 (6)
C2—C3—C7—O1	129.9 (8)	C14—N4—C17—C18	−1.1 (17)
C4—C3—C7—O1	−47.6 (10)	C15—N4—C17—C18	177.0 (11)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.93	2.51	3.435 (10)	170
C14—H14A···O4^i	0.93	2.25	3.166 (8)	167
C18—H18A···O4^i	0.93	2.49	3.405 (11)	169

Symmetry code: (i) x, −y+1/2, z+1/2.