Poly[[[aqua(2,2'-bipyridine-κN,N')zinc(II)]-μ-2-nitroterephthalato-κO:O] monohydrate].

In the title compound, {[Zn(C(8)H(3)NO(6))(C(10)H(8)N(2))(H(2)O)]·H(2)O}(n), the Zn(II) ion is square-pyramidally coordinated, and bridged by 2-nitro-terephthalate ligands, forming a chain running along [10]. Intra-molecular hydrogen bonds are formed between the coordinated water mol-ecules and the nitro O atoms. Adjacent chains are linked by hydrogen bonds between the coordinated water mol-ecules and the O atoms of the monodentate carboxyl groups.

Related literature

Benzene polycarb­oxy­lic acids and nitro­gen hetero aromatic ligands have been used to construct ZnII coordination polymers by hydro­thermal synthesis, see: Huang et al. (2008 ▶); Ma et al. (2005 ▶); Song et al. (2006 ▶); Wang et al. (2005 ▶); Yang et al. (2002 ▶, 2003a ▶,b ▶,c ▶); Zhang et al. (2003 ▶, 2007 ▶); Zhou et al. (2009a ▶) The substituents on the benzene polycarb­oxy­lic acids have been found to play important roles in determining the structures of the coordination polymers, see: Prajapati et al. (2009 ▶); Zhou et al. (2009b ▶).

Experimental

Crystal data

[Zn(C8H3NO6)(C10H8N2)(H2O)]·H2O

M = 466.70

Triclinic,

a = 8.5570 (5) Å

b = 9.1074 (5) Å

c = 12.2060 (7) Å

α = 84.558 (1)°

β = 76.863 (1)°

γ = 73.692 (1)°

V = 888.58 (9) Å3

Z = 2

Mo Kα radiation

μ = 1.44 mm−1

T = 297 K

0.41 × 0.36 × 0.33 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.590, T max = 0.648

5326 measured reflections

3915 independent reflections

3739 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.119

S = 1.10

3915 reflections

285 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.65 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023615/kp2266sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023615/kp2266Isup2.hkl

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

[Zn(C8H3NO6)(C10H8N2)(H2O)]·H2O	Z = 2
Mr = 466.70	F(000) = 476
Triclinic, P1	Dx = 1.744 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5570 (5) Å	Cell parameters from 4213 reflections
b = 9.1074 (5) Å	θ = 2.3–28.5°
c = 12.2060 (7) Å	µ = 1.44 mm−1
α = 84.558 (1)°	T = 297 K
β = 76.863 (1)°	Block, yellow
γ = 73.692 (1)°	0.41 × 0.36 × 0.33 mm
V = 888.58 (9) Å3

Bruker SMART APEX area-detector diffractometer	3915 independent reflections
Radiation source: fine-focus sealed tube	3739 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scan	θmax = 28.6°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
Tmin = 0.590, Tmax = 0.648	k = −11→11
5326 measured reflections	l = −15→13

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0588P)2 + 0.302P] where P = (Fo2 + 2Fc2)/3
3915 reflections	(Δ/σ)max = 0.001
285 parameters	Δρmax = 0.65 e Å−3
4 restraints	Δρmin = −0.39 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.10197 (3)	0.50965 (3)	0.27688 (2)	0.02770 (12)
O1	0.3177 (2)	0.3927 (2)	0.31591 (17)	0.0375 (4)
O1W	−0.0424 (3)	0.4071 (2)	0.40216 (18)	0.0373 (4)
H1A	−0.131 (3)	0.463 (3)	0.440 (3)	0.043 (10)*
H1B	−0.003 (4)	0.340 (3)	0.448 (2)	0.043 (10)*
O2	0.3290 (3)	0.4075 (3)	0.49422 (19)	0.0493 (6)
O2W	0.4501 (5)	0.3808 (4)	0.6976 (2)	0.0700 (8)
H2A	0.425 (6)	0.386 (6)	0.634 (2)	0.084*
H2B	0.547 (3)	0.392 (6)	0.673 (4)	0.084*
O3	1.0362 (3)	−0.2228 (3)	0.4031 (2)	0.0547 (6)
O4	0.9149 (3)	−0.3030 (2)	0.2882 (2)	0.0460 (5)
O5	0.2308 (3)	0.1110 (3)	0.3586 (2)	0.0519 (6)
O6	0.3909 (4)	0.0225 (4)	0.2029 (3)	0.0690 (8)
N1	0.2312 (3)	0.6052 (2)	0.12874 (19)	0.0302 (4)
N2	0.0999 (3)	0.3715 (2)	0.15004 (19)	0.0306 (5)
N3	0.3663 (3)	0.0691 (3)	0.2970 (2)	0.0368 (5)
C1	0.5136 (3)	0.2006 (3)	0.3915 (2)	0.0258 (5)
C2	0.5128 (3)	0.0739 (3)	0.3376 (2)	0.0274 (5)
C3	0.6443 (3)	−0.0554 (3)	0.3223 (2)	0.0317 (5)
H3A	0.6396	−0.1378	0.2847	0.038*
C4	0.7833 (3)	−0.0609 (3)	0.3636 (2)	0.0304 (5)
C5	0.7895 (3)	0.0643 (3)	0.4159 (2)	0.0343 (6)
H5A	0.8840	0.0619	0.4422	0.041*
C6	0.6559 (3)	0.1934 (3)	0.4294 (2)	0.0318 (5)
H6A	0.6621	0.2771	0.4648	0.038*
C7	0.3725 (3)	0.3455 (3)	0.4030 (2)	0.0283 (5)
C8	0.9233 (4)	−0.2058 (3)	0.3517 (2)	0.0376 (6)
C9	0.2869 (4)	0.7290 (3)	0.1244 (3)	0.0378 (6)
H9A	0.2710	0.7795	0.1904	0.045*
C10	0.3665 (4)	0.7837 (3)	0.0258 (3)	0.0440 (7)
H10A	0.4041	0.8703	0.0248	0.053*
C11	0.3905 (4)	0.7090 (4)	−0.0723 (3)	0.0448 (7)
H11A	0.4457	0.7438	−0.1402	0.054*
C12	0.3314 (4)	0.5822 (3)	−0.0682 (2)	0.0395 (6)
H12A	0.3454	0.5303	−0.1333	0.047*
C13	0.2514 (3)	0.5336 (3)	0.0338 (2)	0.0302 (5)
C14	0.1825 (3)	0.3991 (3)	0.0464 (2)	0.0306 (5)
C15	0.1997 (4)	0.3087 (4)	−0.0424 (3)	0.0438 (7)
H15A	0.2559	0.3304	−0.1140	0.053*
C16	0.1324 (5)	0.1859 (4)	−0.0232 (3)	0.0510 (8)
H16A	0.1440	0.1225	−0.0816	0.061*
C17	0.0489 (4)	0.1579 (4)	0.0818 (3)	0.0464 (7)
H17A	0.0020	0.0757	0.0960	0.056*
C18	0.0344 (4)	0.2527 (3)	0.1669 (3)	0.0389 (6)
H18A	−0.0231	0.2332	0.2387	0.047*

	U11	U22	U33	U12	U13	U23
Zn1	0.02659 (18)	0.02438 (17)	0.02802 (18)	0.00097 (12)	−0.00622 (12)	−0.00332 (11)
O1	0.0309 (10)	0.0370 (10)	0.0351 (10)	0.0057 (8)	−0.0081 (8)	0.0037 (8)
O1W	0.0307 (10)	0.0347 (10)	0.0358 (11)	0.0018 (8)	0.0006 (8)	0.0006 (8)
O2	0.0432 (12)	0.0515 (12)	0.0397 (12)	0.0159 (10)	−0.0096 (10)	−0.0196 (10)
O2W	0.096 (2)	0.088 (2)	0.0453 (15)	−0.0528 (19)	−0.0214 (15)	0.0056 (14)
O3	0.0361 (12)	0.0516 (13)	0.0633 (16)	0.0094 (10)	−0.0150 (11)	0.0090 (11)
O4	0.0421 (12)	0.0311 (10)	0.0485 (13)	0.0097 (9)	0.0000 (10)	−0.0035 (9)
O5	0.0312 (11)	0.0619 (14)	0.0611 (15)	−0.0123 (10)	−0.0113 (10)	0.0092 (12)
O6	0.0621 (17)	0.0779 (18)	0.0722 (18)	−0.0005 (14)	−0.0334 (15)	−0.0364 (15)
N1	0.0317 (11)	0.0271 (10)	0.0298 (11)	−0.0043 (8)	−0.0068 (9)	−0.0017 (8)
N2	0.0302 (11)	0.0288 (10)	0.0323 (11)	−0.0032 (8)	−0.0101 (9)	−0.0032 (8)
N3	0.0367 (13)	0.0285 (11)	0.0477 (14)	−0.0062 (9)	−0.0173 (11)	0.0000 (10)
C1	0.0237 (11)	0.0238 (10)	0.0248 (11)	0.0002 (9)	−0.0033 (9)	0.0002 (9)
C2	0.0265 (12)	0.0262 (11)	0.0287 (12)	−0.0051 (9)	−0.0073 (9)	0.0015 (9)
C3	0.0350 (14)	0.0240 (11)	0.0329 (13)	−0.0027 (10)	−0.0055 (11)	−0.0049 (9)
C4	0.0285 (12)	0.0254 (11)	0.0293 (12)	0.0010 (9)	−0.0016 (10)	0.0027 (9)
C5	0.0259 (12)	0.0378 (13)	0.0365 (14)	−0.0012 (10)	−0.0106 (11)	0.0001 (11)
C6	0.0300 (13)	0.0291 (12)	0.0356 (14)	−0.0027 (10)	−0.0103 (11)	−0.0057 (10)
C7	0.0232 (11)	0.0246 (11)	0.0319 (13)	−0.0003 (9)	−0.0028 (10)	−0.0009 (9)
C8	0.0333 (14)	0.0281 (12)	0.0368 (15)	0.0039 (11)	0.0036 (11)	0.0064 (11)
C9	0.0405 (15)	0.0309 (13)	0.0417 (16)	−0.0078 (11)	−0.0087 (12)	−0.0047 (11)
C10	0.0459 (17)	0.0334 (14)	0.0508 (18)	−0.0131 (13)	−0.0053 (14)	0.0033 (12)
C11	0.0468 (17)	0.0478 (17)	0.0371 (16)	−0.0145 (14)	−0.0038 (13)	0.0054 (13)
C12	0.0451 (16)	0.0413 (15)	0.0301 (14)	−0.0093 (12)	−0.0055 (12)	−0.0035 (11)
C13	0.0278 (12)	0.0287 (11)	0.0310 (13)	−0.0008 (10)	−0.0074 (10)	−0.0037 (10)
C14	0.0297 (12)	0.0288 (11)	0.0317 (13)	−0.0017 (10)	−0.0096 (10)	−0.0039 (10)
C15	0.0501 (18)	0.0452 (16)	0.0371 (15)	−0.0095 (14)	−0.0110 (13)	−0.0125 (13)
C16	0.063 (2)	0.0447 (17)	0.053 (2)	−0.0159 (16)	−0.0197 (17)	−0.0158 (14)
C17	0.0522 (19)	0.0402 (15)	0.0542 (19)	−0.0177 (14)	−0.0179 (15)	−0.0055 (14)
C18	0.0406 (15)	0.0386 (14)	0.0385 (15)	−0.0108 (12)	−0.0105 (12)	0.0001 (12)

Zn1—O1	1.9922 (19)	C3—C4	1.381 (4)
Zn1—O1W	2.063 (2)	C3—H3A	0.9300
Zn1—O4i	1.976 (2)	C4—C5	1.377 (4)
Zn1—N1	2.141 (2)	C4—C8	1.506 (3)
Zn1—N2	2.091 (2)	C5—C6	1.383 (4)
O1—C7	1.249 (3)	C5—H5A	0.9300
O1W—H1A	0.85 (3)	C6—H6A	0.9300
O1W—H1B	0.84 (3)	C9—C10	1.366 (4)
O2—C7	1.230 (3)	C9—H9A	0.9300
O2W—H2A	0.85 (3)	C10—C11	1.379 (5)
O2W—H2B	0.85 (3)	C10—H10A	0.9300
O3—C8	1.234 (4)	C11—C12	1.377 (4)
O4—C8	1.257 (4)	C11—H11A	0.9300
O4—Zn1ii	1.976 (2)	C12—C13	1.376 (4)
O5—N3	1.210 (3)	C12—H12A	0.9300
O6—N3	1.215 (3)	C13—C14	1.483 (4)
N1—C9	1.334 (4)	C14—C15	1.380 (4)
N1—C13	1.337 (3)	C15—C16	1.374 (5)
N2—C18	1.332 (4)	C15—H15A	0.9300
N2—C14	1.340 (4)	C16—C17	1.357 (5)
N3—C2	1.461 (3)	C16—H16A	0.9300
C1—C6	1.381 (4)	C17—C18	1.375 (4)
C1—C2	1.384 (3)	C17—H17A	0.9300
C1—C7	1.510 (3)	C18—H18A	0.9300
C2—C3	1.375 (3)
O1—Zn1—O1W	95.05 (8)	C1—C6—C5	121.3 (2)
O1—Zn1—N1	90.59 (8)	C1—C6—H6A	119.3
O1—Zn1—N2	98.69 (9)	C5—C6—H6A	119.3
O1W—Zn1—N1	170.66 (9)	O2—C7—O1	127.0 (2)
O1W—Zn1—N2	94.61 (9)	O2—C7—C1	117.3 (2)
O4i—Zn1—O1	149.63 (10)	O1—C7—C1	115.6 (2)
O4i—Zn1—O1W	89.11 (9)	O3—C8—O4	124.5 (3)
O4i—Zn1—N1	89.79 (9)	O3—C8—C4	119.8 (3)
O4i—Zn1—N2	110.97 (10)	O4—C8—C4	115.8 (3)
N1—Zn1—N2	77.14 (9)	N1—C9—C10	121.9 (3)
C7—O1—Zn1	137.57 (18)	N1—C9—H9A	119.1
Zn1—O1W—H1A	118 (2)	C10—C9—H9A	119.1
Zn1—O1W—H1B	124 (2)	C9—C10—C11	119.2 (3)
H1A—O1W—H1B	106 (3)	C9—C10—H10A	120.4
H2A—O2W—H2B	96 (5)	C11—C10—H10A	120.4
C8—O4—Zn1ii	113.6 (2)	C12—C11—C10	119.0 (3)
C9—N1—C13	119.3 (2)	C12—C11—H11A	120.5
C9—N1—Zn1	125.6 (2)	C10—C11—H11A	120.5
C13—N1—Zn1	115.06 (17)	C13—C12—C11	118.9 (3)
C18—N2—C14	118.6 (2)	C13—C12—H12A	120.6
C18—N2—Zn1	124.7 (2)	C11—C12—H12A	120.6
C14—N2—Zn1	116.48 (18)	N1—C13—C12	121.7 (3)
O5—N3—O6	124.9 (3)	N1—C13—C14	115.5 (2)
O5—N3—C2	118.3 (3)	C12—C13—C14	122.8 (2)
O6—N3—C2	116.7 (3)	N2—C14—C15	121.7 (3)
C6—C1—C2	116.8 (2)	N2—C14—C13	115.6 (2)
C6—C1—C7	120.2 (2)	C15—C14—C13	122.7 (3)
C2—C1—C7	122.9 (2)	C16—C15—C14	118.9 (3)
C3—C2—C1	123.1 (2)	C16—C15—H15A	120.5
C3—C2—N3	116.1 (2)	C14—C15—H15A	120.5
C1—C2—N3	120.8 (2)	C17—C16—C15	119.4 (3)
C2—C3—C4	118.9 (2)	C17—C16—H16A	120.3
C2—C3—H3A	120.6	C15—C16—H16A	120.3
C4—C3—H3A	120.6	C16—C17—C18	119.2 (3)
C5—C4—C3	119.6 (2)	C16—C17—H17A	120.4
C5—C4—C8	121.8 (3)	C18—C17—H17A	120.4
C3—C4—C8	118.6 (3)	N2—C18—C17	122.3 (3)
C4—C5—C6	120.4 (3)	N2—C18—H18A	118.9
C4—C5—H5A	119.8	C17—C18—H18A	118.9
C6—C5—H5A	119.8
O4i—Zn1—O1—C7	58.0 (4)	C6—C1—C7—O2	−46.1 (4)
O1W—Zn1—O1—C7	−38.9 (3)	C2—C1—C7—O2	137.9 (3)
N2—Zn1—O1—C7	−134.3 (3)	C6—C1—C7—O1	130.8 (3)
N1—Zn1—O1—C7	148.6 (3)	C2—C1—C7—O1	−45.1 (3)
O4i—Zn1—N1—C9	64.9 (2)	Zn1ii—O4—C8—O3	0.0 (4)
O1—Zn1—N1—C9	−84.8 (2)	Zn1ii—O4—C8—C4	−179.80 (17)
N2—Zn1—N1—C9	176.5 (2)	C5—C4—C8—O3	10.4 (4)
O4i—Zn1—N1—C13	−113.31 (19)	C3—C4—C8—O3	−168.5 (3)
O1—Zn1—N1—C13	97.06 (19)	C5—C4—C8—O4	−169.8 (3)
N2—Zn1—N1—C13	−1.72 (18)	C3—C4—C8—O4	11.3 (4)
O4i—Zn1—N2—C18	−96.8 (2)	C13—N1—C9—C10	−1.0 (4)
O1—Zn1—N2—C18	89.8 (2)	Zn1—N1—C9—C10	−179.1 (2)
O1W—Zn1—N2—C18	−6.0 (2)	N1—C9—C10—C11	−0.1 (5)
N1—Zn1—N2—C18	178.4 (2)	C9—C10—C11—C12	0.8 (5)
O4i—Zn1—N2—C14	88.66 (19)	C10—C11—C12—C13	−0.4 (5)
O1—Zn1—N2—C14	−84.70 (19)	C9—N1—C13—C12	1.4 (4)
O1W—Zn1—N2—C14	179.47 (18)	Zn1—N1—C13—C12	179.7 (2)
N1—Zn1—N2—C14	3.91 (18)	C9—N1—C13—C14	−178.8 (2)
C6—C1—C2—C3	0.8 (4)	Zn1—N1—C13—C14	−0.5 (3)
C7—C1—C2—C3	176.8 (2)	C11—C12—C13—N1	−0.7 (4)
C6—C1—C2—N3	178.4 (2)	C11—C12—C13—C14	179.5 (3)
C7—C1—C2—N3	−5.5 (4)	C18—N2—C14—C15	0.5 (4)
O5—N3—C2—C3	132.7 (3)	Zn1—N2—C14—C15	175.4 (2)
O6—N3—C2—C3	−47.2 (4)	C18—N2—C14—C13	179.7 (2)
O5—N3—C2—C1	−45.1 (3)	Zn1—N2—C14—C13	−5.4 (3)
O6—N3—C2—C1	135.0 (3)	N1—C13—C14—N2	3.8 (3)
C1—C2—C3—C4	0.8 (4)	C12—C13—C14—N2	−176.4 (2)
N3—C2—C3—C4	−176.9 (2)	N1—C13—C14—C15	−176.9 (3)
C2—C3—C4—C5	−2.0 (4)	C12—C13—C14—C15	2.9 (4)
C2—C3—C4—C8	177.0 (2)	N2—C14—C15—C16	−1.0 (5)
C3—C4—C5—C6	1.5 (4)	C13—C14—C15—C16	179.8 (3)
C8—C4—C5—C6	−177.4 (2)	C14—C15—C16—C17	0.9 (5)
C2—C1—C6—C5	−1.2 (4)	C15—C16—C17—C18	−0.4 (5)
C7—C1—C6—C5	−177.4 (2)	C14—N2—C18—C17	0.1 (4)
C4—C5—C6—C1	0.1 (4)	Zn1—N2—C18—C17	−174.4 (2)
Zn1—O1—C7—O2	−33.2 (5)	C16—C17—C18—N2	−0.1 (5)
Zn1—O1—C7—C1	150.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2iii	0.85 (3)	1.83 (3)	2.670 (3)	174 (4)
O1W—H1B···O3iv	0.84 (3)	2.02 (2)	2.779 (3)	150 (3)
O1W—H1B···O5	0.84 (3)	2.58 (3)	3.031 (3)	115 (3)
O2W—H2A···O2	0.85 (3)	2.03 (3)	2.865 (4)	171 (5)
O2W—H2B···O1v	0.85 (3)	2.57 (4)	3.213 (4)	134 (4)

Zn1—O1	1.9922 (19)
Zn1—O1W	2.063 (2)
Zn1—O4i	1.976 (2)
Zn1—N1	2.141 (2)
Zn1—N2	2.091 (2)

O1—Zn1—O1W	95.05 (8)
O1—Zn1—N1	90.59 (8)
O1—Zn1—N2	98.69 (9)
O1W—Zn1—N1	170.66 (9)
O1W—Zn1—N2	94.61 (9)
O4i—Zn1—O1	149.63 (10)
O4i—Zn1—O1W	89.11 (9)
O4i—Zn1—N1	89.79 (9)
O4i—Zn1—N2	110.97 (10)
N1—Zn1—N2	77.14 (9)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O2ii	0.85 (3)	1.83 (3)	2.670 (3)	174 (4)
O1W—H1B⋯O3iii	0.84 (3)	2.02 (2)	2.779 (3)	150 (3)
O1W—H1B⋯O5	0.84 (3)	2.58 (3)	3.031 (3)	115 (3)
O2W—H2A⋯O2	0.85 (3)	2.03 (3)	2.865 (4)	171 (5)
O2W—H2B⋯O1iv	0.85 (3)	2.57 (4)	3.213 (4)	134 (4)

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