catena-Poly[[bis-(1-methyl-1H-imidazole-κN)zinc]-μ-3-nitro-phthalato-κO:O].

In the title complex, [Zn(C(8)H(3)NO(6))(C(4)H(6)N(2))(2)](n), the carboxyl-ate groups of the 3-nitro-phthalate dianion ligand coordinate the Zn(II) ion in a bis-monodentate mode. The Zn(II) ion shows distorted tetra-hedral coordination as it is bonded to two O atoms from the carboxyl-ate groups of symmetry-related 3-nitro-phthalate anions and two N atoms of two independent 1-methyl-imidazole mol-ecules. The bridging 3-nitro-phthalate ligand allows the formation of one-dimensional chains in the c direction. The crystal structure is further stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For related structures with methyl­imidazole, see: Baca et al. (2003 ▶, 2004 ▶); Zhao (2008 ▶). For related coordination modes of phthalate and substituted phthalate with metal, see: Biagini Cingi et al. (1978 ▶); Guo & Guo (2007 ▶); Ma et al. (2004 ▶); Wang et al. (2009 ▶); Yang et al. (2003 ▶).

Experimental

Crystal data

[Zn(C8H3NO6)(C4H6N2)2]

M = 438.70

Monoclinic,

a = 8.375 (2) Å

b = 16.005 (4) Å

c = 14.057 (4) Å

β = 102.618 (4)°

V = 1838.7 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.38 mm−1

T = 294 K

0.18 × 0.06 × 0.06 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.883, T max = 0.921

13428 measured reflections

3240 independent reflections

2904 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.074

S = 1.06

3240 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.37 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812004576/bh2410sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004576/bh2410Isup2.hkl

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

[Zn(C8H3NO6)(C4H6N2)2]	F(000) = 896
Mr = 438.70	Dx = 1.585 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6551 reflections
a = 8.375 (2) Å	θ = 1.5–27.9°
b = 16.005 (4) Å	µ = 1.38 mm−1
c = 14.057 (4) Å	T = 294 K
β = 102.618 (4)°	Needle, colorless
V = 1838.7 (8) Å3	0.18 × 0.06 × 0.06 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	3240 independent reflections
Radiation source: rotating anode	2904 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.027
Detector resolution: 28.57 pixels mm-1	θmax = 25.0°, θmin = 2.0°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −19→18
Tmin = 0.883, Tmax = 0.921	l = −16→16
13428 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0448P)2 + 0.3182P] where P = (Fo2 + 2Fc2)/3
3240 reflections	(Δ/σ)max = 0.009
255 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.37 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Zn1	0.37841 (3)	0.207619 (14)	0.455381 (16)	0.01901 (10)
O1	0.40470 (16)	0.33302 (8)	0.29849 (10)	0.0208 (3)
O2	0.21557 (17)	0.27506 (9)	0.36867 (10)	0.0232 (3)
O3	0.25521 (18)	0.36236 (9)	0.02871 (10)	0.0240 (3)
O4	0.21554 (18)	0.24772 (9)	0.11179 (10)	0.0247 (3)
O5	0.1941 (2)	0.44350 (11)	0.44209 (11)	0.0380 (4)
O6	−0.0626 (2)	0.41913 (11)	0.43565 (12)	0.0429 (4)
N1	0.4567 (2)	0.12574 (10)	0.36701 (12)	0.0205 (4)
N2	0.4793 (2)	0.05951 (11)	0.23352 (12)	0.0242 (4)
N3	0.5739 (2)	0.25540 (11)	0.54444 (12)	0.0230 (4)
N4	0.7568 (2)	0.28401 (11)	0.67687 (13)	0.0282 (4)
N5	0.0545 (2)	0.42875 (11)	0.39749 (13)	0.0289 (4)
C1	0.2635 (2)	0.32439 (12)	0.30897 (13)	0.0178 (4)
C2	0.1264 (2)	0.37573 (12)	0.24794 (14)	0.0180 (4)
C3	0.0247 (3)	0.42461 (13)	0.29116 (15)	0.0246 (5)
C4	−0.0997 (3)	0.47334 (15)	0.23928 (17)	0.0353 (6)
H4	−0.1657	0.5046	0.2712	0.042*
C5	−0.1245 (3)	0.47481 (16)	0.13908 (17)	0.0392 (6)
H5	−0.2058	0.5085	0.1026	0.047*
C6	−0.0277 (3)	0.42597 (14)	0.09312 (16)	0.0320 (5)
H6	−0.0457	0.4265	0.0255	0.038*
C7	0.0960 (2)	0.37607 (12)	0.14624 (14)	0.0205 (4)
C8	0.1969 (2)	0.32282 (13)	0.09277 (14)	0.0208 (4)
C9	0.4173 (2)	0.12626 (12)	0.27040 (15)	0.0217 (5)
H9	0.3547	0.1675	0.2331	0.026*
C10	0.5501 (3)	0.05407 (14)	0.39165 (16)	0.0283 (5)
H10	0.5967	0.0371	0.4549	0.034*
C11	0.5631 (3)	0.01286 (14)	0.31019 (16)	0.0302 (5)
H11	0.6178	−0.0372	0.3066	0.036*
C12	0.4611 (3)	0.03974 (15)	0.13012 (16)	0.0350 (6)
H12A	0.3992	0.0830	0.0914	0.053*
H12B	0.4050	−0.0126	0.1161	0.053*
H12C	0.5673	0.0358	0.1150	0.053*
C13	0.6139 (3)	0.24697 (13)	0.64004 (15)	0.0244 (5)
H13	0.5510	0.2190	0.6768	0.029*
C14	0.6993 (3)	0.30033 (14)	0.51958 (17)	0.0305 (5)
H14	0.7046	0.3160	0.4566	0.037*
C15	0.8124 (3)	0.31792 (15)	0.60038 (17)	0.0344 (6)
H15	0.9094	0.3473	0.6039	0.041*
C16	0.8332 (3)	0.29180 (16)	0.78106 (17)	0.0407 (6)
H16A	0.8170	0.3474	0.8027	0.061*
H16B	0.9483	0.2807	0.7910	0.061*
H16C	0.7842	0.2524	0.8176	0.061*

	U11	U22	U33	U12	U13	U23
Zn1	0.02000 (15)	0.01878 (15)	0.01866 (14)	−0.00048 (9)	0.00515 (10)	0.00074 (9)
O1	0.0161 (8)	0.0221 (8)	0.0249 (7)	0.0007 (6)	0.0061 (6)	0.0011 (6)
O2	0.0216 (8)	0.0265 (8)	0.0231 (7)	0.0019 (6)	0.0087 (6)	0.0072 (6)
O3	0.0287 (8)	0.0241 (8)	0.0211 (7)	0.0016 (6)	0.0099 (6)	−0.0014 (6)
O4	0.0267 (9)	0.0216 (8)	0.0249 (8)	0.0037 (6)	0.0036 (6)	−0.0006 (6)
O5	0.0327 (10)	0.0483 (11)	0.0323 (9)	0.0025 (8)	0.0058 (7)	−0.0094 (8)
O6	0.0411 (11)	0.0552 (11)	0.0412 (10)	0.0013 (9)	0.0285 (8)	−0.0008 (9)
N1	0.0228 (10)	0.0190 (9)	0.0207 (9)	0.0013 (7)	0.0068 (7)	0.0010 (7)
N2	0.0248 (10)	0.0224 (9)	0.0269 (9)	−0.0005 (8)	0.0086 (8)	−0.0023 (8)
N3	0.0197 (9)	0.0255 (10)	0.0245 (9)	−0.0002 (7)	0.0066 (7)	−0.0014 (8)
N4	0.0187 (10)	0.0357 (11)	0.0295 (10)	0.0015 (8)	0.0036 (8)	−0.0062 (8)
N5	0.0340 (12)	0.0273 (10)	0.0289 (10)	0.0058 (8)	0.0146 (9)	−0.0006 (8)
C1	0.0217 (11)	0.0157 (10)	0.0163 (10)	−0.0006 (8)	0.0047 (8)	−0.0030 (8)
C2	0.0163 (10)	0.0169 (10)	0.0220 (10)	−0.0001 (8)	0.0066 (8)	0.0023 (8)
C3	0.0248 (12)	0.0261 (12)	0.0251 (11)	0.0029 (9)	0.0106 (9)	0.0013 (9)
C4	0.0301 (14)	0.0393 (14)	0.0395 (14)	0.0162 (11)	0.0142 (11)	0.0017 (11)
C5	0.0300 (14)	0.0484 (16)	0.0380 (14)	0.0215 (11)	0.0047 (11)	0.0079 (12)
C6	0.0279 (13)	0.0407 (14)	0.0257 (12)	0.0086 (10)	0.0027 (9)	0.0041 (10)
C7	0.0166 (11)	0.0221 (11)	0.0232 (10)	0.0011 (8)	0.0052 (8)	0.0009 (9)
C8	0.0165 (11)	0.0261 (12)	0.0175 (10)	0.0002 (9)	−0.0013 (8)	−0.0027 (9)
C9	0.0187 (11)	0.0176 (11)	0.0292 (11)	−0.0002 (8)	0.0058 (8)	0.0011 (9)
C10	0.0273 (13)	0.0291 (12)	0.0285 (11)	0.0057 (10)	0.0059 (9)	0.0088 (10)
C11	0.0305 (13)	0.0240 (12)	0.0375 (13)	0.0091 (10)	0.0104 (10)	0.0043 (10)
C12	0.0433 (15)	0.0348 (13)	0.0287 (12)	−0.0035 (11)	0.0115 (11)	−0.0080 (11)
C13	0.0206 (11)	0.0263 (12)	0.0269 (11)	0.0016 (9)	0.0066 (9)	−0.0010 (9)
C14	0.0286 (13)	0.0348 (13)	0.0313 (13)	−0.0064 (10)	0.0134 (10)	−0.0026 (10)
C15	0.0237 (13)	0.0396 (14)	0.0425 (14)	−0.0095 (10)	0.0129 (10)	−0.0082 (12)
C16	0.0277 (14)	0.0570 (17)	0.0324 (14)	0.0029 (11)	−0.0047 (10)	−0.0035 (12)

Zn1—O2	1.9454 (14)	C2—C7	1.396 (3)
Zn1—O3i	1.9612 (14)	C3—C4	1.376 (3)
Zn1—N3	1.9841 (17)	C4—C5	1.378 (3)
Zn1—N1	2.0116 (17)	C4—H4	0.9300
O1—C1	1.231 (2)	C5—C6	1.383 (3)
O2—C1	1.279 (2)	C5—H5	0.9300
O3—C8	1.281 (2)	C6—C7	1.389 (3)
O4—C8	1.234 (2)	C6—H6	0.9300
O5—N5	1.223 (2)	C7—C8	1.511 (3)
O6—N5	1.226 (2)	C9—H9	0.9300
N1—C9	1.326 (3)	C10—C11	1.346 (3)
N1—C10	1.389 (3)	C10—H10	0.9300
N2—C9	1.341 (3)	C11—H11	0.9300
N2—C11	1.371 (3)	C12—H12A	0.9600
N2—C12	1.463 (3)	C12—H12B	0.9600
N3—C13	1.319 (3)	C12—H12C	0.9600
N3—C14	1.380 (3)	C13—H13	0.9300
N4—C13	1.335 (3)	C14—C15	1.340 (3)
N4—C15	1.373 (3)	C14—H14	0.9300
N4—C16	1.470 (3)	C15—H15	0.9300
N5—C3	1.462 (3)	C16—H16A	0.9600
C1—C2	1.516 (3)	C16—H16B	0.9600
C2—C3	1.390 (3)	C16—H16C	0.9600
O2—Zn1—O3i	105.60 (6)	C5—C6—H6	119.4
O2—Zn1—N3	123.39 (7)	C7—C6—H6	119.4
O3i—Zn1—N3	110.17 (7)	C6—C7—C2	120.04 (19)
O2—Zn1—N1	104.66 (6)	C6—C7—C8	119.29 (18)
O3i—Zn1—N1	103.44 (7)	C2—C7—C8	120.67 (17)
N3—Zn1—N1	107.78 (7)	O4—C8—O3	125.73 (19)
C1—O2—Zn1	118.44 (13)	O4—C8—C7	119.97 (18)
C8—O3—Zn1ii	114.34 (13)	O3—C8—C7	114.30 (17)
C9—N1—C10	105.16 (17)	N1—C9—N2	111.11 (18)
C9—N1—Zn1	125.92 (14)	N1—C9—H9	124.4
C10—N1—Zn1	128.74 (14)	N2—C9—H9	124.4
C9—N2—C11	107.74 (17)	C11—C10—N1	109.76 (19)
C9—N2—C12	126.27 (18)	C11—C10—H10	125.1
C11—N2—C12	125.99 (19)	N1—C10—H10	125.1
C13—N3—C14	105.86 (18)	C10—C11—N2	106.23 (19)
C13—N3—Zn1	126.48 (15)	C10—C11—H11	126.9
C14—N3—Zn1	127.59 (15)	N2—C11—H11	126.9
C13—N4—C15	107.49 (19)	N2—C12—H12A	109.5
C13—N4—C16	125.6 (2)	N2—C12—H12B	109.5
C15—N4—C16	126.8 (2)	H12A—C12—H12B	109.5
O5—N5—O6	124.51 (19)	N2—C12—H12C	109.5
O5—N5—C3	117.59 (18)	H12A—C12—H12C	109.5
O6—N5—C3	117.88 (19)	H12B—C12—H12C	109.5
O1—C1—O2	126.52 (18)	N3—C13—N4	110.9 (2)
O1—C1—C2	119.99 (17)	N3—C13—H13	124.6
O2—C1—C2	113.49 (17)	N4—C13—H13	124.6
C3—C2—C7	116.93 (18)	C15—C14—N3	109.3 (2)
C3—C2—C1	121.21 (17)	C15—C14—H14	125.3
C7—C2—C1	121.86 (17)	N3—C14—H14	125.3
C4—C3—C2	123.5 (2)	C14—C15—N4	106.4 (2)
C4—C3—N5	117.16 (19)	C14—C15—H15	126.8
C2—C3—N5	119.23 (18)	N4—C15—H15	126.8
C3—C4—C5	118.6 (2)	N4—C16—H16A	109.5
C3—C4—H4	120.7	N4—C16—H16B	109.5
C5—C4—H4	120.7	H16A—C16—H16B	109.5
C4—C5—C6	119.7 (2)	N4—C16—H16C	109.5
C4—C5—H5	120.2	H16A—C16—H16C	109.5
C6—C5—H5	120.2	H16B—C16—H16C	109.5
C5—C6—C7	121.2 (2)
O3i—Zn1—O2—C1	−177.09 (13)	C4—C5—C6—C7	−0.9 (4)
N3—Zn1—O2—C1	55.12 (16)	C5—C6—C7—C2	−1.2 (3)
N1—Zn1—O2—C1	−68.28 (15)	C5—C6—C7—C8	179.1 (2)
O2—Zn1—N1—C9	7.11 (18)	C3—C2—C7—C6	2.2 (3)
O3i—Zn1—N1—C9	117.49 (17)	C1—C2—C7—C6	−178.04 (19)
N3—Zn1—N1—C9	−125.83 (17)	C3—C2—C7—C8	−178.14 (18)
O2—Zn1—N1—C10	−167.15 (17)	C1—C2—C7—C8	1.7 (3)
O3i—Zn1—N1—C10	−56.76 (19)	Zn1ii—O3—C8—O4	1.6 (3)
N3—Zn1—N1—C10	59.91 (19)	Zn1ii—O3—C8—C7	−177.52 (12)
O2—Zn1—N3—C13	121.96 (17)	C6—C7—C8—O4	−129.1 (2)
O3i—Zn1—N3—C13	−3.9 (2)	C2—C7—C8—O4	51.2 (3)
N1—Zn1—N3—C13	−116.05 (18)	C6—C7—C8—O3	50.1 (3)
O2—Zn1—N3—C14	−61.5 (2)	C2—C7—C8—O3	−129.6 (2)
O3i—Zn1—N3—C14	172.64 (17)	C10—N1—C9—N2	0.3 (2)
N1—Zn1—N3—C14	60.4 (2)	Zn1—N1—C9—N2	−175.08 (13)
Zn1—O2—C1—O1	1.6 (3)	C11—N2—C9—N1	0.3 (2)
Zn1—O2—C1—C2	−177.94 (12)	C12—N2—C9—N1	−179.79 (19)
O1—C1—C2—C3	−125.2 (2)	C9—N1—C10—C11	−0.7 (2)
O2—C1—C2—C3	54.5 (2)	Zn1—N1—C10—C11	174.44 (15)
O1—C1—C2—C7	55.0 (3)	N1—C10—C11—N2	0.9 (3)
O2—C1—C2—C7	−125.3 (2)	C9—N2—C11—C10	−0.7 (2)
C7—C2—C3—C4	−1.3 (3)	C12—N2—C11—C10	179.3 (2)
C1—C2—C3—C4	178.9 (2)	C14—N3—C13—N4	0.1 (2)
C7—C2—C3—N5	−178.00 (18)	Zn1—N3—C13—N4	177.23 (14)
C1—C2—C3—N5	2.2 (3)	C15—N4—C13—N3	−0.3 (2)
O5—N5—C3—C4	−127.4 (2)	C16—N4—C13—N3	175.7 (2)
O6—N5—C3—C4	50.9 (3)	C13—N3—C14—C15	0.1 (3)
O5—N5—C3—C2	49.5 (3)	Zn1—N3—C14—C15	−176.93 (16)
O6—N5—C3—C2	−132.1 (2)	N3—C14—C15—N4	−0.3 (3)
C2—C3—C4—C5	−0.7 (4)	C13—N4—C15—C14	0.4 (3)
N5—C3—C4—C5	176.1 (2)	C16—N4—C15—C14	−175.5 (2)
C3—C4—C5—C6	1.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O4	0.93	2.25	3.156 (3)	166
C11—H11···O1iii	0.93	2.53	3.297 (3)	140
C12—H12A···O5ii	0.96	2.44	3.078 (3)	124
C13—H13···O1i	0.93	2.46	3.373 (3)	169
C16—H16B···O2iv	0.96	2.44	3.345 (3)	158

Table 1

Selected bond angles (°)

O2—Zn1—O3i	105.60 (6)
O2—Zn1—N3	123.39 (7)
O3i—Zn1—N3	110.17 (7)
O2—Zn1—N1	104.66 (6)
O3i—Zn1—N1	103.44 (7)
N3—Zn1—N1	107.78 (7)
O1—C1—O2	126.52 (18)
O4—C8—O3	125.73 (19)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O4	0.93	2.25	3.156 (3)	166
C11—H11⋯O1ii	0.93	2.53	3.297 (3)	140
C12—H12A⋯O5iii	0.96	2.44	3.078 (3)	124
C13—H13⋯O1i	0.93	2.46	3.373 (3)	169
C16—H16B⋯O2iv	0.96	2.44	3.345 (3)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .