Diaqua-(5-carb-oxy-benzene-1,3-di-carboxyl-ato-κO)(4,4'-dimethyl-2,2'-bipyridine-κN,N')zinc.

In the title compound, [Zn(C(9)H(4)O(6))(C(12)H(12)N(2))(H(2)O)(2)], the Zn(II) atom is five-coordinated by two N atoms from a 4,4'-dimethyl-2,2'-bipyridine ligand, one O atom from a 5-carb-oxy-benzene-1,3-dicarboxyl-ate ligand and two water mol-ecules in a distorted trigonal-bipyramidal geometry. The complex mol-ecules are linked by inter-molecular O-H⋯O hydrogen bonds and partly overlapping π-π inter-actions [centroid-centroid distance = 4.017 (2) Å] into a three-dimensional supra-molecular network.

Related literature

For background to the network topologies and applications of coordination polymers, see: Maspoch et al. (2007 ▶); Ockwig et al. (2005 ▶); Zang et al. (2006 ▶). For O—H⋯O hydrogen bonds, see: Desiraju et al. (2004 ▶). For π–π inter­actions, see: Zang et al. (2010 ▶).

Experimental

Crystal data

[Zn(C9H4O6)(C12H12N2)(H2O)2]

M = 493.76

Triclinic,

a = 9.1938 (9) Å

b = 10.7978 (8) Å

c = 11.5842 (7) Å

α = 85.238 (6)°

β = 72.960 (7)°

γ = 69.760 (8)°

V = 1031.40 (16) Å3

Z = 2

Mo Kα radiation

μ = 1.24 mm−1

T = 296 K

0.21 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.780, T max = 0.798

7701 measured reflections

3607 independent reflections

3246 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.089

S = 1.05

3607 reflections

292 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019519/hy2433sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019519/hy2433Isup2.hkl

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

[Zn(C9H4O6)(C12H12N2)(H2O)2]	Z = 2
Mr = 493.76	F(000) = 508
Triclinic, P1	Dx = 1.590 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1938 (9) Å	Cell parameters from 4795 reflections
b = 10.7978 (8) Å	θ = 3.5–29.1°
c = 11.5842 (7) Å	µ = 1.24 mm−1
α = 85.238 (6)°	T = 296 K
β = 72.960 (7)°	Block, colorless
γ = 69.760 (8)°	0.21 × 0.20 × 0.19 mm
V = 1031.40 (16) Å3

Bruker APEXII CCD diffractometer	3607 independent reflections
Radiation source: fine-focus sealed tube	3246 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 25.0°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.780, Tmax = 0.798	k = −12→12
7701 measured reflections	l = −13→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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0516P)2] where P = (Fo2 + 2Fc2)/3
3607 reflections	(Δ/σ)max = 0.009
292 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

	x	y	z	Uiso*/Ueq
Zn1	0.29959 (3)	0.80971 (2)	0.41463 (2)	0.02705 (12)
O1	0.3344 (2)	0.21247 (17)	0.51057 (18)	0.0451 (5)
O2	0.1654 (2)	0.11417 (16)	0.62226 (18)	0.0417 (5)
O3	0.1815 (2)	0.68960 (16)	0.50550 (15)	0.0353 (4)
O4	−0.0341 (2)	0.81358 (16)	0.64551 (17)	0.0442 (5)
O5	−0.4023 (2)	0.60517 (15)	0.91517 (15)	0.0378 (4)
H5A	−0.4810	0.5991	0.9684	0.057*
O6	−0.3417 (2)	0.38720 (15)	0.90916 (15)	0.0377 (4)
O1W	0.34722 (19)	0.87467 (15)	0.55069 (14)	0.0310 (4)
H1WA	0.4474	0.8605	0.5349	0.046*
H1WB	0.2920	0.9551	0.5668	0.046*
O2W	0.1124 (2)	0.92769 (15)	0.35858 (16)	0.0380 (4)
H2WA	0.0254	0.9106	0.3765	0.057*
H2WB	0.0912	1.0101	0.3581	0.057*
N1	0.4831 (2)	0.64334 (18)	0.31684 (17)	0.0294 (4)
N2	0.4584 (2)	0.89292 (18)	0.27789 (18)	0.0313 (5)
C1	0.2061 (3)	0.2140 (2)	0.5853 (2)	0.0295 (5)
C2	0.0560 (3)	0.7072 (2)	0.5941 (2)	0.0277 (5)
C3	−0.3103 (3)	0.4905 (2)	0.8723 (2)	0.0257 (5)
C4	0.0878 (3)	0.3468 (2)	0.6388 (2)	0.0244 (5)
C5	−0.0533 (3)	0.3572 (2)	0.7292 (2)	0.0261 (5)
H5	−0.0770	0.2816	0.7590	0.031*
C6	−0.1601 (3)	0.4811 (2)	0.7756 (2)	0.0254 (5)
C7	−0.1244 (3)	0.5936 (2)	0.73168 (19)	0.0246 (5)
H7	−0.1955	0.6759	0.7635	0.030*
C8	0.0167 (3)	0.5847 (2)	0.6404 (2)	0.0241 (5)
C9	0.1210 (3)	0.4604 (2)	0.5950 (2)	0.0256 (5)
H9	0.2154	0.4532	0.5337	0.031*
C10	0.4961 (3)	0.5176 (2)	0.3444 (2)	0.0352 (6)
H10	0.4184	0.5014	0.4101	0.042*
C11	0.6183 (3)	0.4113 (2)	0.2805 (2)	0.0378 (6)
H11	0.6214	0.3259	0.3027	0.045*
C12	0.7357 (3)	0.4315 (2)	0.1840 (2)	0.0341 (6)
C13	0.8735 (4)	0.3183 (3)	0.1126 (3)	0.0495 (7)
H13A	0.9377	0.2685	0.1638	0.074*
H13B	0.9394	0.3519	0.0463	0.074*
H13C	0.8313	0.2621	0.0821	0.074*
C14	0.7234 (3)	0.5617 (2)	0.1547 (2)	0.0319 (6)
H14	0.8002	0.5794	0.0894	0.038*
C15	0.5972 (3)	0.6652 (2)	0.2222 (2)	0.0269 (5)
C16	0.5789 (3)	0.8062 (2)	0.1965 (2)	0.0278 (5)
C17	0.6761 (3)	0.8476 (2)	0.0971 (2)	0.0374 (6)
H17	0.7560	0.7855	0.0409	0.045*
C18	0.6557 (3)	0.9805 (2)	0.0801 (2)	0.0384 (6)
C19	0.7596 (4)	1.0268 (3)	−0.0278 (3)	0.0604 (9)
H19A	0.8531	1.0303	−0.0091	0.091*
H19B	0.6990	1.1132	−0.0489	0.091*
H19C	0.7930	0.9666	−0.0946	0.091*
C20	0.5346 (3)	1.0673 (3)	0.1677 (3)	0.0436 (7)
H20	0.5178	1.1574	0.1616	0.052*
C21	0.4393 (3)	1.0211 (2)	0.2634 (2)	0.0398 (6)
H21	0.3581	1.0815	0.3204	0.048*

	U11	U22	U33	U12	U13	U23
Zn1	0.02375 (18)	0.02181 (17)	0.03013 (18)	−0.00935 (12)	0.00191 (12)	0.00227 (11)
O1	0.0236 (10)	0.0374 (10)	0.0601 (12)	−0.0075 (8)	0.0085 (9)	−0.0093 (9)
O2	0.0267 (9)	0.0214 (8)	0.0687 (13)	−0.0072 (7)	−0.0004 (9)	−0.0071 (8)
O3	0.0319 (10)	0.0301 (9)	0.0400 (10)	−0.0185 (7)	0.0036 (8)	0.0062 (7)
O4	0.0418 (11)	0.0204 (8)	0.0559 (12)	−0.0106 (8)	0.0066 (9)	0.0036 (8)
O5	0.0326 (10)	0.0273 (9)	0.0371 (10)	−0.0088 (8)	0.0132 (8)	−0.0019 (7)
O6	0.0350 (10)	0.0280 (9)	0.0419 (10)	−0.0160 (8)	0.0064 (8)	0.0056 (8)
O1W	0.0220 (9)	0.0236 (8)	0.0419 (10)	−0.0063 (7)	−0.0016 (8)	−0.0038 (7)
O2W	0.0299 (10)	0.0224 (8)	0.0614 (12)	−0.0118 (7)	−0.0109 (9)	0.0087 (8)
N1	0.0298 (11)	0.0249 (10)	0.0308 (10)	−0.0114 (8)	−0.0025 (9)	0.0018 (8)
N2	0.0269 (11)	0.0269 (10)	0.0334 (11)	−0.0088 (9)	0.0008 (9)	0.0014 (9)
C1	0.0227 (13)	0.0257 (12)	0.0387 (14)	−0.0066 (10)	−0.0073 (11)	−0.0044 (10)
C2	0.0272 (13)	0.0243 (12)	0.0321 (13)	−0.0128 (10)	−0.0062 (11)	0.0086 (10)
C3	0.0262 (12)	0.0240 (12)	0.0236 (11)	−0.0099 (10)	−0.0011 (10)	0.0021 (9)
C4	0.0211 (12)	0.0230 (11)	0.0294 (12)	−0.0099 (9)	−0.0048 (10)	0.0009 (9)
C5	0.0281 (13)	0.0202 (11)	0.0304 (12)	−0.0121 (10)	−0.0052 (10)	0.0046 (9)
C6	0.0237 (12)	0.0256 (11)	0.0258 (11)	−0.0107 (10)	−0.0033 (10)	0.0029 (9)
C7	0.0232 (12)	0.0196 (11)	0.0270 (12)	−0.0075 (9)	−0.0008 (10)	0.0003 (9)
C8	0.0220 (12)	0.0240 (11)	0.0256 (11)	−0.0099 (9)	−0.0040 (10)	0.0037 (9)
C9	0.0198 (12)	0.0273 (12)	0.0286 (12)	−0.0122 (9)	−0.0004 (10)	0.0016 (10)
C10	0.0410 (15)	0.0290 (13)	0.0341 (13)	−0.0167 (11)	−0.0040 (12)	0.0064 (11)
C11	0.0471 (17)	0.0233 (12)	0.0422 (15)	−0.0103 (11)	−0.0149 (13)	0.0060 (11)
C12	0.0369 (15)	0.0291 (13)	0.0359 (14)	−0.0065 (11)	−0.0144 (12)	−0.0011 (11)
C13	0.0533 (19)	0.0326 (14)	0.0516 (17)	−0.0004 (13)	−0.0134 (15)	−0.0062 (13)
C14	0.0288 (14)	0.0317 (13)	0.0305 (13)	−0.0088 (10)	−0.0033 (11)	0.0012 (10)
C15	0.0244 (12)	0.0296 (12)	0.0249 (12)	−0.0096 (10)	−0.0043 (10)	0.0030 (10)
C16	0.0250 (13)	0.0258 (12)	0.0303 (12)	−0.0090 (10)	−0.0050 (10)	0.0033 (10)
C17	0.0323 (14)	0.0343 (13)	0.0343 (14)	−0.0098 (11)	0.0054 (12)	0.0006 (11)
C18	0.0371 (15)	0.0327 (13)	0.0425 (15)	−0.0160 (12)	−0.0046 (12)	0.0101 (12)
C19	0.063 (2)	0.0489 (18)	0.062 (2)	−0.0310 (16)	0.0061 (17)	0.0128 (16)
C20	0.0425 (16)	0.0268 (13)	0.0559 (17)	−0.0132 (12)	−0.0060 (14)	0.0082 (12)
C21	0.0383 (15)	0.0256 (12)	0.0456 (15)	−0.0087 (11)	0.0008 (13)	−0.0008 (11)

Zn1—O1W	1.9922 (16)	C7—C8	1.392 (3)
Zn1—O2W	2.0018 (16)	C7—H7	0.9300
Zn1—O3	2.0115 (16)	C8—C9	1.389 (3)
Zn1—N1	2.1159 (19)	C9—H9	0.9300
Zn1—N2	2.1826 (19)	C10—C11	1.374 (4)
O1—C1	1.238 (3)	C10—H10	0.9300
O2—C1	1.262 (3)	C11—C12	1.370 (4)
O3—C2	1.268 (3)	C11—H11	0.9300
O4—C2	1.235 (3)	C12—C14	1.391 (3)
O5—C3	1.275 (3)	C12—C13	1.506 (4)
O5—H5A	0.8200	C13—H13A	0.9600
O6—C3	1.257 (3)	C13—H13B	0.9600
O1W—H1WA	0.8444	C13—H13C	0.9600
O1W—H1WB	0.8446	C14—C15	1.387 (3)
O2W—H2WA	0.8460	C14—H14	0.9300
O2W—H2WB	0.8421	C15—C16	1.487 (3)
N1—C10	1.341 (3)	C16—C17	1.382 (3)
N1—C15	1.346 (3)	C17—C18	1.386 (3)
N2—C21	1.336 (3)	C17—H17	0.9300
N2—C16	1.346 (3)	C18—C20	1.386 (4)
C1—C4	1.516 (3)	C18—C19	1.501 (4)
C2—C8	1.505 (3)	C19—H19A	0.9600
C3—C6	1.480 (3)	C19—H19B	0.9600
C4—C5	1.384 (3)	C19—H19C	0.9600
C4—C9	1.386 (3)	C20—C21	1.374 (4)
C5—C6	1.394 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.384 (3)
O1W—Zn1—O2W	117.76 (7)	C7—C8—C2	120.5 (2)
O1W—Zn1—O3	99.49 (7)	C4—C9—C8	121.6 (2)
O2W—Zn1—O3	94.51 (7)	C4—C9—H9	119.2
O1W—Zn1—N1	115.84 (7)	C8—C9—H9	119.2
O2W—Zn1—N1	124.77 (8)	N1—C10—C11	123.3 (2)
O3—Zn1—N1	89.06 (7)	N1—C10—H10	118.3
O1W—Zn1—N2	93.17 (7)	C11—C10—H10	118.3
O2W—Zn1—N2	89.03 (7)	C12—C11—C10	119.9 (2)
O3—Zn1—N2	163.37 (7)	C12—C11—H11	120.1
N1—Zn1—N2	75.66 (7)	C10—C11—H11	120.1
C2—O3—Zn1	133.53 (15)	C11—C12—C14	117.2 (2)
C3—O5—H5A	109.5	C11—C12—C13	121.7 (2)
Zn1—O1W—H1WA	110.1	C14—C12—C13	121.0 (2)
Zn1—O1W—H1WB	111.0	C12—C13—H13A	109.5
H1WA—O1W—H1WB	112.2	C12—C13—H13B	109.5
Zn1—O2W—H2WA	119.9	H13A—C13—H13B	109.5
Zn1—O2W—H2WB	120.2	C12—C13—H13C	109.5
H2WA—O2W—H2WB	109.6	H13A—C13—H13C	109.5
C10—N1—C15	117.7 (2)	H13B—C13—H13C	109.5
C10—N1—Zn1	124.60 (16)	C15—C14—C12	120.5 (2)
C15—N1—Zn1	117.70 (14)	C15—C14—H14	119.7
C21—N2—C16	118.1 (2)	C12—C14—H14	119.7
C21—N2—Zn1	125.98 (17)	N1—C15—C14	121.4 (2)
C16—N2—Zn1	115.76 (15)	N1—C15—C16	115.7 (2)
O1—C1—O2	125.7 (2)	C14—C15—C16	123.0 (2)
O1—C1—C4	117.5 (2)	N2—C16—C17	121.5 (2)
O2—C1—C4	116.8 (2)	N2—C16—C15	114.79 (19)
O4—C2—O3	126.4 (2)	C17—C16—C15	123.7 (2)
O4—C2—C8	118.0 (2)	C16—C17—C18	120.8 (2)
O3—C2—C8	115.6 (2)	C16—C17—H17	119.6
O6—C3—O5	123.0 (2)	C18—C17—H17	119.6
O6—C3—C6	119.6 (2)	C17—C18—C20	116.4 (2)
O5—C3—C6	117.45 (19)	C17—C18—C19	121.4 (2)
C5—C4—C9	119.4 (2)	C20—C18—C19	122.2 (2)
C5—C4—C1	121.50 (19)	C18—C19—H19A	109.5
C9—C4—C1	119.1 (2)	C18—C19—H19B	109.5
C4—C5—C6	119.9 (2)	H19A—C19—H19B	109.5
C4—C5—H5	120.0	C18—C19—H19C	109.5
C6—C5—H5	120.0	H19A—C19—H19C	109.5
C7—C6—C5	120.0 (2)	H19B—C19—H19C	109.5
C7—C6—C3	120.7 (2)	C21—C20—C18	120.3 (2)
C5—C6—C3	119.27 (19)	C21—C20—H20	119.8
C6—C7—C8	120.7 (2)	C18—C20—H20	119.8
C6—C7—H7	119.6	N2—C21—C20	122.7 (2)
C8—C7—H7	119.6	N2—C21—H21	118.6
C9—C8—C7	118.4 (2)	C20—C21—H21	118.6
C9—C8—C2	121.1 (2)
O1W—Zn1—O3—C2	57.8 (2)	O4—C2—C8—C9	−173.5 (2)
O2W—Zn1—O3—C2	−61.4 (2)	O3—C2—C8—C9	5.7 (3)
N1—Zn1—O3—C2	173.8 (2)	O4—C2—C8—C7	5.3 (3)
N2—Zn1—O3—C2	−163.2 (2)	O3—C2—C8—C7	−175.5 (2)
O1W—Zn1—N1—C10	89.3 (2)	C5—C4—C9—C8	0.6 (3)
O2W—Zn1—N1—C10	−105.6 (2)	C1—C4—C9—C8	179.8 (2)
O3—Zn1—N1—C10	−10.8 (2)	C7—C8—C9—C4	−0.3 (3)
N2—Zn1—N1—C10	175.8 (2)	C2—C8—C9—C4	178.6 (2)
O1W—Zn1—N1—C15	−88.84 (17)	C15—N1—C10—C11	−0.6 (4)
O2W—Zn1—N1—C15	76.23 (18)	Zn1—N1—C10—C11	−178.77 (19)
O3—Zn1—N1—C15	171.07 (17)	N1—C10—C11—C12	0.7 (4)
N2—Zn1—N1—C15	−2.30 (16)	C10—C11—C12—C14	−0.6 (4)
O1W—Zn1—N2—C21	−63.8 (2)	C10—C11—C12—C13	179.0 (2)
O2W—Zn1—N2—C21	54.0 (2)	C11—C12—C14—C15	0.5 (4)
O3—Zn1—N2—C21	156.6 (2)	C13—C12—C14—C15	−179.0 (2)
N1—Zn1—N2—C21	−179.6 (2)	C10—N1—C15—C14	0.5 (3)
O1W—Zn1—N2—C16	121.32 (17)	Zn1—N1—C15—C14	178.81 (18)
O2W—Zn1—N2—C16	−120.94 (18)	C10—N1—C15—C16	−179.1 (2)
O3—Zn1—N2—C16	−18.3 (4)	Zn1—N1—C15—C16	−0.8 (3)
N1—Zn1—N2—C16	5.44 (17)	C12—C14—C15—N1	−0.5 (4)
Zn1—O3—C2—O4	3.8 (4)	C12—C14—C15—C16	179.1 (2)
Zn1—O3—C2—C8	−175.34 (15)	C21—N2—C16—C17	−3.1 (4)
O1—C1—C4—C5	−175.4 (2)	Zn1—N2—C16—C17	172.22 (19)
O2—C1—C4—C5	3.9 (3)	C21—N2—C16—C15	177.2 (2)
O1—C1—C4—C9	5.5 (3)	Zn1—N2—C16—C15	−7.5 (3)
O2—C1—C4—C9	−175.3 (2)	N1—C15—C16—N2	5.6 (3)
C9—C4—C5—C6	−0.3 (3)	C14—C15—C16—N2	−174.0 (2)
C1—C4—C5—C6	−179.5 (2)	N1—C15—C16—C17	−174.1 (2)
C4—C5—C6—C7	−0.3 (3)	C14—C15—C16—C17	6.2 (4)
C4—C5—C6—C3	−179.9 (2)	N2—C16—C17—C18	2.2 (4)
O6—C3—C6—C7	178.6 (2)	C15—C16—C17—C18	−178.1 (2)
O5—C3—C6—C7	−1.8 (3)	C16—C17—C18—C20	0.2 (4)
O6—C3—C6—C5	−1.8 (3)	C16—C17—C18—C19	−179.6 (3)
O5—C3—C6—C5	177.8 (2)	C17—C18—C20—C21	−1.6 (4)
C5—C6—C7—C8	0.7 (3)	C19—C18—C20—C21	178.2 (3)
C3—C6—C7—C8	−179.8 (2)	C16—N2—C21—C20	1.7 (4)
C6—C7—C8—C9	−0.3 (3)	Zn1—N2—C21—C20	−173.1 (2)
C6—C7—C8—C2	−179.2 (2)	C18—C20—C21—N2	0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O6i	0.82	1.79	2.603 (2)	171
O1W—H1WA···O1ii	0.84	1.81	2.635 (2)	165
O1W—H1WB···O2iii	0.84	1.75	2.593 (2)	171
O2W—H2WA···O2iv	0.85	1.86	2.688 (2)	166
O2W—H2WB···O4v	0.84	1.79	2.633 (2)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O6i	0.82	1.79	2.603 (2)	171
O1W—H1WA⋯O1ii	0.84	1.81	2.635 (2)	165
O1W—H1WB⋯O2iii	0.84	1.75	2.593 (2)	171
O2W—H2WA⋯O2iv	0.85	1.86	2.688 (2)	166
O2W—H2WB⋯O4v	0.84	1.79	2.633 (2)	176

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