Poly[chlorido[μ(4)-2,2'-(2-methyl-1H-benzimidazol-3-ium-1,3-di-yl)diacetato]-zinc].

The title compound, [Zn(C(12)H(11)N(2)O(4))Cl](n), contains a centrosymmetric dimetal tetra-carboxyl-ate paddle-wheel moiety in which the Zn(II) atom is square-pyramidally coordinated by four carboxyl-ate O atoms at the basal positions and one Cl(-) anion at the apical position. Each paddle-wheel unit is joined to four such neighbours through bridging dicarboxyl-ate ligands, producing a two-dimensional undulating layer parallel to (-101). Adjacent sheets are stacked in a parallel fashion to form a three-dimensional supra-molecular structure which is stabilized by inter-layer π-π inter-actions between benzene rings, with a centroid-centroid distance of 3.722 Å. The range of Zn-O bond lengths is 2.0440 (17)-2.1256 (15) Å and the Zn-Cl bond length is 2.2622 (6) Å.

Related literature

For background to and potential applications of carboxyl­ate-containing coordination polymers, see Bourne et al. (2001 ▶); Chen et al. (2005 ▶); Kitagawa et al. (2004 ▶); Li et al. (2012 ▶); Xuan et al. (2012 ▶).

Experimental

Crystal data

[Zn(C12H11N2O4)Cl]

M = 348.05

Monoclinic,

a = 7.1285 (17) Å

b = 13.301 (3) Å

c = 12.804 (3) Å

β = 90.540 (4)°

V = 1214.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.26 mm−1

T = 173 K

0.48 × 0.32 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.424, T max = 0.508

6072 measured reflections

2640 independent reflections

2327 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.078

S = 1.07

2640 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.45 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812020077/bg2452sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020077/bg2452Isup2.hkl

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

[Zn(C12H11N2O4)Cl]	Z = 4
Mr = 348.05	F(000) = 704
Monoclinic, P21/n	Dx = 1.904 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.1285 (17) Å	θ = 2.2–27.1°
b = 13.301 (3) Å	µ = 2.26 mm−1
c = 12.804 (3) Å	T = 173 K
β = 90.540 (4)°	Block, colorless
V = 1214.0 (5) Å3	0.48 × 0.32 × 0.30 mm

Bruker SMART CCD area-detector diffractometer	2640 independent reflections
Radiation source: fine-focus sealed tube	2327 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scans	θmax = 27.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→8
Tmin = 0.424, Tmax = 0.508	k = −11→17
6072 measured reflections	l = −16→9

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0438P)2 + 0.6356P] where P = (Fo2 + 2Fc2)/3
2640 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

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
Zn1	0.13104 (3)	0.553340 (17)	0.417142 (17)	0.01203 (10)
Cl1	0.29440 (7)	0.65999 (4)	0.31470 (4)	0.01697 (13)
O1	0.4360 (2)	0.84000 (11)	0.97522 (12)	0.0181 (3)
O2	0.2502 (2)	0.91230 (12)	1.09352 (13)	0.0217 (4)
O3	0.2669 (2)	0.56544 (13)	0.55787 (12)	0.0241 (4)
O4	0.0830 (2)	0.49535 (12)	0.67900 (12)	0.0203 (3)
N1	0.3143 (2)	0.58092 (13)	0.83280 (13)	0.0122 (3)
N2	0.2081 (2)	0.67202 (13)	0.96116 (14)	0.0131 (4)
C1	0.2938 (3)	0.51606 (15)	0.91696 (16)	0.0123 (4)
C2	0.3314 (3)	0.41392 (16)	0.92770 (17)	0.0164 (4)
H2A	0.3829	0.3755	0.8724	0.020*
C3	0.2899 (3)	0.37134 (16)	1.02313 (18)	0.0190 (5)
H3A	0.3135	0.3018	1.0338	0.023*
C4	0.2140 (3)	0.42806 (17)	1.10429 (18)	0.0190 (5)
H4A	0.1854	0.3957	1.1683	0.023*
C5	0.1792 (3)	0.53041 (16)	1.09412 (16)	0.0157 (4)
H5A	0.1280	0.5689	1.1495	0.019*
C6	0.2235 (3)	0.57346 (15)	0.99858 (16)	0.0133 (4)
C7	0.2610 (3)	0.67345 (15)	0.86146 (16)	0.0128 (4)
C8	0.2578 (3)	0.75932 (16)	0.78819 (17)	0.0197 (5)
H8A	0.2142	0.8196	0.8246	0.030*
H8B	0.1726	0.7443	0.7297	0.030*
H8C	0.3844	0.7709	0.7617	0.030*
C9	0.1487 (3)	0.75902 (15)	1.02331 (17)	0.0159 (4)
H9A	0.1187	0.7357	1.0946	0.019*
H9B	0.0321	0.7867	0.9920	0.019*
C10	0.2944 (3)	0.84401 (15)	1.03157 (16)	0.0136 (4)
C11	0.3852 (3)	0.55606 (16)	0.72945 (16)	0.0142 (4)
H11A	0.4637	0.4948	0.7348	0.017*
H11B	0.4662	0.6116	0.7051	0.017*
C12	0.2295 (3)	0.53811 (15)	0.64823 (17)	0.0138 (4)

	U11	U22	U33	U12	U13	U23
Zn1	0.01287 (15)	0.01381 (14)	0.00939 (14)	−0.00070 (8)	−0.00114 (9)	0.00073 (8)
Cl1	0.0203 (3)	0.0164 (2)	0.0142 (2)	−0.00402 (19)	0.00246 (19)	−0.00035 (18)
O1	0.0171 (8)	0.0169 (7)	0.0205 (8)	−0.0037 (6)	0.0038 (6)	−0.0020 (6)
O2	0.0251 (9)	0.0166 (7)	0.0235 (8)	−0.0044 (6)	0.0047 (7)	−0.0089 (7)
O3	0.0191 (8)	0.0415 (10)	0.0114 (8)	−0.0005 (7)	−0.0032 (6)	0.0026 (7)
O4	0.0199 (8)	0.0227 (8)	0.0181 (8)	−0.0067 (7)	−0.0050 (6)	−0.0012 (6)
N1	0.0123 (8)	0.0143 (8)	0.0100 (8)	−0.0009 (7)	−0.0026 (6)	−0.0012 (7)
N2	0.0136 (9)	0.0126 (8)	0.0130 (8)	−0.0012 (7)	−0.0004 (7)	−0.0009 (7)
C1	0.0113 (10)	0.0153 (10)	0.0102 (9)	−0.0027 (8)	−0.0039 (7)	−0.0003 (8)
C2	0.0161 (10)	0.0153 (10)	0.0176 (10)	0.0004 (8)	−0.0048 (8)	−0.0025 (8)
C3	0.0172 (11)	0.0136 (10)	0.0261 (12)	−0.0031 (8)	−0.0065 (9)	0.0049 (9)
C4	0.0170 (11)	0.0222 (11)	0.0178 (11)	−0.0050 (9)	−0.0047 (8)	0.0066 (9)
C5	0.0153 (10)	0.0206 (10)	0.0112 (10)	−0.0045 (8)	−0.0019 (8)	−0.0014 (8)
C6	0.0117 (9)	0.0136 (9)	0.0145 (10)	−0.0035 (8)	−0.0032 (8)	−0.0012 (8)
C7	0.0110 (9)	0.0150 (10)	0.0121 (9)	−0.0027 (8)	−0.0038 (7)	−0.0015 (8)
C8	0.0264 (12)	0.0172 (10)	0.0154 (10)	0.0003 (9)	−0.0016 (9)	0.0030 (9)
C9	0.0154 (10)	0.0131 (10)	0.0191 (10)	−0.0007 (8)	0.0028 (8)	−0.0055 (8)
C10	0.0152 (10)	0.0131 (9)	0.0126 (9)	−0.0012 (8)	−0.0025 (8)	−0.0003 (8)
C11	0.0134 (10)	0.0198 (11)	0.0093 (9)	0.0010 (8)	−0.0014 (8)	−0.0014 (8)
C12	0.0142 (10)	0.0150 (10)	0.0121 (9)	0.0045 (8)	−0.0034 (8)	−0.0034 (8)

Zn1—O3	2.0440 (17)	C2—H2A	0.9500
Zn1—O4i	2.0559 (16)	C3—C4	1.397 (3)
Zn1—O2ii	2.0632 (16)	C3—H3A	0.9500
Zn1—O1iii	2.1256 (15)	C4—C5	1.390 (3)
Zn1—Cl1	2.2622 (6)	C4—H4A	0.9500
O1—C10	1.247 (3)	C5—C6	1.390 (3)
O2—C10	1.248 (3)	C5—H5A	0.9500
O3—C12	1.244 (3)	C7—C8	1.478 (3)
O4—C12	1.256 (3)	C8—H8A	0.9800
N1—C7	1.340 (3)	C8—H8B	0.9800
N1—C1	1.389 (3)	C8—H8C	0.9800
N1—C11	1.459 (3)	C9—C10	1.538 (3)
N2—C7	1.335 (3)	C9—H9A	0.9900
N2—C6	1.400 (3)	C9—H9B	0.9900
N2—C9	1.469 (3)	C11—C12	1.532 (3)
C1—C2	1.391 (3)	C11—H11A	0.9900
C1—C6	1.392 (3)	C11—H11B	0.9900
C2—C3	1.381 (3)
O3—Zn1—O4i	153.56 (7)	C6—C5—H5A	121.8
O3—Zn1—O2ii	86.48 (7)	C4—C5—H5A	121.8
O4i—Zn1—O2ii	88.65 (7)	C5—C6—C1	121.4 (2)
O3—Zn1—O1iii	86.86 (7)	C5—C6—N2	132.0 (2)
O4i—Zn1—O1iii	86.31 (7)	C1—C6—N2	106.52 (18)
O2ii—Zn1—O1iii	154.17 (6)	N2—C7—N1	109.40 (18)
O3—Zn1—Cl1	102.68 (5)	N2—C7—C8	127.98 (19)
O4i—Zn1—Cl1	103.50 (5)	N1—C7—C8	122.58 (19)
O2ii—Zn1—Cl1	108.55 (5)	C7—C8—H8A	109.5
O1iii—Zn1—Cl1	97.25 (5)	C7—C8—H8B	109.5
C10—O1—Zn1iv	135.18 (14)	H8A—C8—H8B	109.5
C10—O2—Zn1v	120.91 (14)	C7—C8—H8C	109.5
C12—O3—Zn1	133.86 (15)	H8A—C8—H8C	109.5
C12—O4—Zn1i	124.71 (14)	H8B—C8—H8C	109.5
C7—N1—C1	109.00 (17)	N2—C9—C10	114.73 (17)
C7—N1—C11	123.92 (17)	N2—C9—H9A	108.6
C1—N1—C11	127.07 (18)	C10—C9—H9A	108.6
C7—N2—C6	108.60 (17)	N2—C9—H9B	108.6
C7—N2—C9	126.32 (18)	C10—C9—H9B	108.6
C6—N2—C9	125.06 (18)	H9A—C9—H9B	107.6
N1—C1—C2	131.4 (2)	O1—C10—O2	127.5 (2)
N1—C1—C6	106.45 (18)	O1—C10—C9	118.58 (18)
C2—C1—C6	122.14 (19)	O2—C10—C9	113.85 (18)
C3—C2—C1	116.4 (2)	N1—C11—C12	113.33 (17)
C3—C2—H2A	121.8	N1—C11—H11A	108.9
C1—C2—H2A	121.8	C12—C11—H11A	108.9
C2—C3—C4	121.6 (2)	N1—C11—H11B	108.9
C2—C3—H3A	119.2	C12—C11—H11B	108.9
C4—C3—H3A	119.2	H11A—C11—H11B	107.7
C5—C4—C3	122.0 (2)	O3—C12—O4	127.6 (2)
C5—C4—H4A	119.0	O3—C12—C11	115.17 (19)
C3—C4—H4A	119.0	O4—C12—C11	117.18 (19)
C6—C5—C4	116.4 (2)