Bis(1-methyl-4-oxoimidazolidin-2-iminium) diaqua-bis-(pyridine-2,4-dicarboxyl-ato-κN,O)zincate(II) dihydrate.

In the title compound, (C(4)H(8)N(3)O)(2)[Zn(C(7)H(3)NO(4))(2)(H(2)O)(2)]·2H(2)O, the Zn(II) ion is six-coordinated in a distorted octa-hedral geometry by two pyridine-2,4-dicarboxyl-ate (pydc) ligands in the equatorial plane and two water mol-ecules in the axial positions. The pydc ligands act as bidentate chelating ligands through one carboxyl-ate O atom and the pyridine N atom. Inter-molecular N-H⋯O, O-H⋯O and weak C-H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For a review article on proton-transfer compounds, see: Aghabozorg et al. (2008b ▶). For related structures, see: Aghabozorg et al. (2008a ▶,c ▶); Attar Gharamaleki et al. (2009 ▶); Moghimi et al. (2004 ▶, 2005 ▶).

Experimental

Crystal data

(C4H8N3O)2[Zn(C7H3NO4)2(H2O)2]·2H2O

M = 695.93

Triclinic,

a = 5.3209 (11) Å

b = 8.3893 (17) Å

c = 16.621 (3) Å

α = 81.58 (3)°

β = 85.26 (3)°

γ = 74.09 (3)°

V = 705.1 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.96 mm−1

T = 298 K

0.30 × 0.20 × 0.15 mm

Data collection

Stoe IPDS-2 diffractometer

Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ▶) T min = 0.793, T max = 0.862

7743 measured reflections

3787 independent reflections

3206 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.090

S = 1.05

3787 reflections

226 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.48 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008452/hy2411sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008452/hy2411Isup2.hkl

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

(C4H8N3O)2[Zn(C7H3NO4)2(H2O)2]·2H2O	Z = 1
Mr = 695.93	F(000) = 360.0
Triclinic, P1	Dx = 1.639 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3209 (11) Å	Cell parameters from 3787 reflections
b = 8.3893 (17) Å	θ = 2.5–29.2°
c = 16.621 (3) Å	µ = 0.96 mm−1
α = 81.58 (3)°	T = 298 K
β = 85.26 (3)°	Block, colorless
γ = 74.09 (3)°	0.30 × 0.20 × 0.15 mm
V = 705.1 (3) Å3

Stoe IPDS-2 diffractometer	3787 independent reflections
Radiation source: fine-focus sealed tube	3206 reflections with I > 2σ(I)
graphite	Rint = 0.043
ω scans	θmax = 29.2°, θmin = 2.5°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	h = −7→7
Tmin = 0.793, Tmax = 0.862	k = −11→11
7743 measured reflections	l = −18→22

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.059P)2] where P = (Fo2 + 2Fc2)/3
3787 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.46 e Å−3
1 restraint	Δρmin = −0.48 e Å−3

	x	y	z	Uiso*/Ueq
Zn1	0.5000	0.0000	0.5000	0.02707 (9)
O1	0.2451 (2)	0.02688 (14)	0.40534 (7)	0.0301 (2)
O2	0.1143 (3)	0.18980 (16)	0.28950 (8)	0.0395 (3)
O3	0.4093 (3)	0.72611 (16)	0.22032 (9)	0.0432 (3)
O4	0.7237 (3)	0.74523 (17)	0.29581 (9)	0.0462 (4)
O5	0.8365 (2)	−0.13001 (16)	0.42711 (8)	0.0325 (3)
O6	0.1878 (3)	0.07267 (19)	0.03511 (9)	0.0476 (3)
O7	0.0855 (4)	0.6692 (3)	0.09580 (15)	0.0641 (5)
N1	0.5314 (2)	0.22674 (15)	0.43582 (8)	0.0239 (2)
N2	0.6139 (3)	0.25207 (17)	0.11654 (9)	0.0313 (3)
N3	0.4814 (3)	0.02055 (17)	0.13579 (9)	0.0305 (3)
N4	0.7948 (3)	0.03970 (18)	0.22119 (10)	0.0379 (4)
H4B	0.8947	0.0943	0.2359	0.045*
H4A	0.7965	−0.0579	0.2462	0.045*
C1	0.3894 (3)	0.27280 (17)	0.36902 (9)	0.0228 (3)
C2	0.3856 (3)	0.41957 (18)	0.31741 (9)	0.0266 (3)
H2	0.2819	0.4505	0.2724	0.032*
C3	0.5398 (3)	0.51957 (17)	0.33430 (9)	0.0252 (3)
C4	0.6886 (3)	0.46909 (18)	0.40272 (10)	0.0282 (3)
H4	0.7951	0.5326	0.4151	0.034*
C5	0.6774 (3)	0.32360 (19)	0.45239 (10)	0.0277 (3)
H5	0.7746	0.2921	0.4988	0.033*
C6	0.2358 (3)	0.15364 (18)	0.35239 (9)	0.0251 (3)
C7	0.5555 (3)	0.67753 (19)	0.27867 (10)	0.0302 (3)
C8	0.6413 (3)	0.10458 (19)	0.16135 (10)	0.0275 (3)
C9	0.3457 (3)	0.1124 (2)	0.07056 (11)	0.0322 (3)
C10	0.4348 (3)	0.2712 (2)	0.05257 (11)	0.0348 (4)
H10A	0.5227	0.2790	−0.0008	0.042*
H10B	0.2887	0.3694	0.0555	0.042*
C11	0.7495 (4)	0.3769 (2)	0.12415 (12)	0.0360 (4)
H11A	0.8693	0.3364	0.1673	0.054*
H11B	0.6247	0.4781	0.1362	0.054*
H11C	0.8445	0.3988	0.0739	0.054*
H3	0.453 (6)	−0.081 (4)	0.155 (2)	0.076 (9)*
H7A	0.113 (8)	0.685 (5)	0.136 (2)	0.085 (13)*
H5B	0.952 (5)	−0.078 (3)	0.4112 (15)	0.048 (7)*
H7B	0.025 (7)	0.763 (5)	0.072 (2)	0.083 (11)*
H5A	0.818 (6)	−0.174 (3)	0.3900 (14)	0.060 (8)*

	U11	U22	U33	U12	U13	U23
Zn1	0.03224 (15)	0.02409 (13)	0.02854 (15)	−0.01705 (9)	−0.01220 (10)	0.00935 (9)
O1	0.0344 (6)	0.0286 (5)	0.0326 (6)	−0.0204 (4)	−0.0115 (5)	0.0074 (4)
O2	0.0513 (7)	0.0399 (6)	0.0359 (7)	−0.0273 (6)	−0.0237 (6)	0.0088 (5)
O3	0.0569 (8)	0.0353 (6)	0.0435 (7)	−0.0273 (6)	−0.0233 (6)	0.0156 (5)
O4	0.0700 (9)	0.0397 (7)	0.0419 (7)	−0.0400 (7)	−0.0218 (7)	0.0124 (5)
O5	0.0335 (6)	0.0362 (6)	0.0326 (6)	−0.0182 (5)	−0.0065 (5)	−0.0004 (5)
O6	0.0467 (8)	0.0542 (8)	0.0483 (8)	−0.0211 (6)	−0.0229 (6)	−0.0009 (7)
O7	0.0781 (13)	0.0550 (10)	0.0624 (12)	−0.0174 (9)	−0.0188 (10)	−0.0093 (9)
N1	0.0256 (6)	0.0233 (5)	0.0251 (6)	−0.0117 (4)	−0.0077 (5)	0.0029 (4)
N2	0.0348 (7)	0.0267 (6)	0.0343 (7)	−0.0152 (5)	−0.0096 (6)	0.0081 (5)
N3	0.0394 (7)	0.0280 (6)	0.0295 (7)	−0.0187 (5)	−0.0106 (6)	0.0031 (5)
N4	0.0529 (9)	0.0315 (7)	0.0369 (8)	−0.0264 (6)	−0.0225 (7)	0.0119 (6)
C1	0.0247 (6)	0.0227 (6)	0.0242 (7)	−0.0125 (5)	−0.0057 (5)	0.0013 (5)
C2	0.0323 (7)	0.0246 (6)	0.0254 (7)	−0.0140 (6)	−0.0099 (6)	0.0053 (5)
C3	0.0301 (7)	0.0208 (6)	0.0268 (7)	−0.0121 (5)	−0.0059 (6)	0.0028 (5)
C4	0.0328 (8)	0.0247 (7)	0.0321 (8)	−0.0164 (6)	−0.0092 (6)	0.0013 (6)
C5	0.0313 (7)	0.0266 (7)	0.0286 (7)	−0.0141 (6)	−0.0130 (6)	0.0041 (6)
C6	0.0269 (7)	0.0254 (6)	0.0273 (7)	−0.0149 (5)	−0.0071 (6)	0.0010 (5)
C7	0.0424 (9)	0.0228 (6)	0.0296 (8)	−0.0173 (6)	−0.0054 (6)	0.0024 (6)
C8	0.0335 (8)	0.0254 (7)	0.0269 (7)	−0.0152 (6)	−0.0047 (6)	0.0024 (6)
C9	0.0321 (8)	0.0349 (8)	0.0308 (8)	−0.0108 (6)	−0.0080 (6)	−0.0005 (6)
C10	0.0338 (8)	0.0338 (8)	0.0354 (9)	−0.0111 (6)	−0.0113 (7)	0.0094 (7)
C11	0.0402 (9)	0.0273 (7)	0.0435 (10)	−0.0180 (6)	−0.0069 (7)	0.0055 (7)

Zn1—N1	2.0819 (14)	N3—H3	0.91 (4)
Zn1—O1	2.1087 (13)	N4—C8	1.298 (2)
Zn1—O5	2.1957 (15)	N4—H4B	0.8600
O1—C6	1.2696 (18)	N4—H4A	0.8600
O2—C6	1.2303 (19)	C1—C2	1.390 (2)
O3—C7	1.244 (2)	C1—C6	1.520 (2)
O4—C7	1.254 (2)	C2—C3	1.393 (2)
O5—H5B	0.85 (3)	C2—H2	0.9300
O5—H5A	0.79 (2)	C3—C4	1.387 (2)
O6—C9	1.207 (2)	C3—C7	1.519 (2)
O7—H7A	0.74 (4)	C4—C5	1.383 (2)
O7—H7B	0.82 (4)	C4—H4	0.9300
N1—C5	1.3367 (19)	C5—H5	0.9300
N1—C1	1.3437 (19)	C9—C10	1.514 (3)
N2—C8	1.325 (2)	C10—H10A	0.9700
N2—C10	1.449 (2)	C10—H10B	0.9700
N2—C11	1.449 (2)	C11—H11A	0.9600
N3—C9	1.368 (2)	C11—H11B	0.9600
N3—C8	1.370 (2)	C11—H11C	0.9600
N1—Zn1—N1i	180.000 (1)	C1—C2—H2	120.6
N1—Zn1—O1	79.39 (5)	C3—C2—H2	120.6
N1i—Zn1—O1	100.61 (5)	C4—C3—C2	118.38 (13)
N1—Zn1—O1i	100.61 (5)	C4—C3—C7	119.66 (14)
N1i—Zn1—O1i	79.39 (5)	C2—C3—C7	121.92 (14)
O1—Zn1—O1i	180.00 (4)	C5—C4—C3	119.50 (14)
N1—Zn1—O5	89.26 (6)	C5—C4—H4	120.2
N1i—Zn1—O5	90.74 (6)	C3—C4—H4	120.2
O1—Zn1—O5	91.70 (5)	N1—C5—C4	122.15 (14)
O1i—Zn1—O5	88.30 (5)	N1—C5—H5	118.9
N1—Zn1—O5i	90.74 (6)	C4—C5—H5	118.9
N1i—Zn1—O5i	89.26 (6)	O2—C6—O1	126.60 (14)
O1—Zn1—O5i	88.30 (5)	O2—C6—C1	117.01 (13)
O1i—Zn1—O5i	91.70 (5)	O1—C6—C1	116.38 (13)
O5—Zn1—O5i	180.000 (1)	O3—C7—O4	125.95 (15)
C6—O1—Zn1	114.83 (9)	O3—C7—C3	118.71 (14)
Zn1—O5—H5B	116.8 (17)	O4—C7—C3	115.32 (14)
Zn1—O5—H5A	121 (2)	N4—C8—N2	127.93 (15)
H5B—O5—H5A	106 (3)	N4—C8—N3	121.60 (14)
H7A—O7—H7B	103 (4)	N2—C8—N3	110.47 (13)
C5—N1—C1	118.96 (13)	O6—C9—N3	126.13 (17)
C5—N1—Zn1	127.89 (10)	O6—C9—C10	127.74 (16)
C1—N1—Zn1	113.12 (10)	N3—C9—C10	106.12 (14)
C8—N2—C10	110.12 (14)	N2—C10—C9	102.65 (13)
C8—N2—C11	127.22 (14)	N2—C10—H10A	111.2
C10—N2—C11	122.56 (14)	C9—C10—H10A	111.2
C9—N3—C8	110.51 (14)	N2—C10—H10B	111.2
C9—N3—H3	118 (2)	C9—C10—H10B	111.2
C8—N3—H3	131 (2)	H10A—C10—H10B	109.2
C8—N4—H4B	120.0	N2—C11—H11A	109.5
C8—N4—H4A	120.0	N2—C11—H11B	109.5
H4B—N4—H4A	120.0	H11A—C11—H11B	109.5
N1—C1—C2	122.12 (13)	N2—C11—H11C	109.5
N1—C1—C6	116.08 (12)	H11A—C11—H11C	109.5
C2—C1—C6	121.80 (13)	H11B—C11—H11C	109.5
C1—C2—C3	118.85 (13)
N1—Zn1—O1—C6	3.82 (11)	C3—C4—C5—N1	1.5 (3)
N1i—Zn1—O1—C6	−176.18 (11)	Zn1—O1—C6—O2	175.35 (14)
O5—Zn1—O1—C6	−85.11 (12)	Zn1—O1—C6—C1	−5.02 (18)
O5i—Zn1—O1—C6	94.89 (12)	N1—C1—C6—O2	−176.70 (15)
O1—Zn1—N1—C5	−179.66 (15)	C2—C1—C6—O2	2.4 (2)
O1i—Zn1—N1—C5	0.34 (15)	N1—C1—C6—O1	3.6 (2)
O5—Zn1—N1—C5	−87.80 (14)	C2—C1—C6—O1	−177.22 (14)
O5i—Zn1—N1—C5	92.20 (14)	C4—C3—C7—O3	−175.83 (16)
O1—Zn1—N1—C1	−1.69 (11)	C2—C3—C7—O3	6.3 (3)
O1i—Zn1—N1—C1	178.31 (11)	C4—C3—C7—O4	5.8 (2)
O5—Zn1—N1—C1	90.17 (11)	C2—C3—C7—O4	−172.14 (17)
O5i—Zn1—N1—C1	−89.83 (11)	C10—N2—C8—N4	176.19 (18)
C5—N1—C1—C2	−1.2 (2)	C11—N2—C8—N4	−0.2 (3)
Zn1—N1—C1—C2	−179.41 (12)	C10—N2—C8—N3	−3.2 (2)
C5—N1—C1—C6	177.91 (14)	C11—N2—C8—N3	−179.64 (17)
Zn1—N1—C1—C6	−0.26 (17)	C9—N3—C8—N4	−178.09 (16)
N1—C1—C2—C3	1.9 (2)	C9—N3—C8—N2	1.4 (2)
C6—C1—C2—C3	−177.24 (14)	C8—N3—C9—O6	−179.20 (18)
C1—C2—C3—C4	−0.8 (2)	C8—N3—C9—C10	1.0 (2)
C1—C2—C3—C7	177.16 (15)	C8—N2—C10—C9	3.57 (19)
C2—C3—C4—C5	−0.8 (2)	C11—N2—C10—C9	−179.80 (16)
C7—C3—C4—C5	−178.81 (15)	O6—C9—C10—N2	177.51 (19)
C1—N1—C5—C4	−0.5 (2)	N3—C9—C10—N2	−2.67 (19)
Zn1—N1—C5—C4	177.40 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3ii	0.91 (3)	1.87 (3)	2.764 (2)	165 (3)
N4—H4A···O4ii	0.86	1.86	2.706 (2)	168
N4—H4B···O2iii	0.86	1.92	2.771 (2)	169
O5—H5A···O4ii	0.79 (2)	1.95 (3)	2.729 (2)	171 (3)
O5—H5B···O1iii	0.85 (3)	1.98 (3)	2.8088 (17)	165 (2)
O7—H7A···O3	0.73 (4)	2.32 (4)	2.968 (3)	148 (4)
O7—H7B···O6iv	0.82 (4)	2.26 (4)	2.993 (3)	149 (4)
C5—H5···O5v	0.93	2.46	3.308 (2)	152
C11—H11A···O2iii	0.96	2.48	3.425 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O3i	0.91 (3)	1.87 (3)	2.764 (2)	165 (3)
N4—H4A⋯O4i	0.86	1.86	2.706 (2)	168
N4—H4B⋯O2ii	0.86	1.92	2.771 (2)	169
O5—H5A⋯O4i	0.79 (2)	1.95 (3)	2.729 (2)	171 (3)
O5—H5B⋯O1ii	0.85 (3)	1.98 (3)	2.8088 (17)	165 (2)
O7—H7A⋯O3	0.73 (4)	2.32 (4)	2.968 (3)	148 (4)
O7—H7B⋯O6iii	0.82 (4)	2.26 (4)	2.993 (3)	149 (4)
C5—H5⋯O5iv	0.93	2.46	3.308 (2)	152
C11—H11A⋯O2ii	0.96	2.48	3.425 (3)	167

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