Diaqua-bis-(4-carb-oxy-2-propyl-1H-imidazole-5-carboxyl-ato-κN,O)zinc(II) N,N-dimethyl-formamide disolvate.

In the crystal structure of the title compound, [Zn(C(8)H(9)N(2)O(4))(2)(H(2)O)(2)]·2C(3)H(7)NO, the Zn(II) atom is coordinated by two N,O-bidentate 2-propyl-1H-imidazole-4,5-dicarboxyl-ate anions and two water mol-ecules in a distorted octa-hedral environment. The asymmetric unit consists of one Zn(II) atom located on a center of inversion as well as one anion, one water mol-ecule and one additional dimethyl-formamide mol-ecule that occupy general positions. Between the carboxyl and the carboxyl-ate group an intra-molecular hydrogen bond is found in which the hydroxy H atom is disordered. Disorder is also found for the H atoms of one of the three methyl groups. In the crystal structure, additional inter-molecular N-H⋯O and O-H⋯O hydrogen bonding is found.

Related literature

For imidazole-4,5-dicarb­oxy­lic complexes, see: Maji et al. (2005 ▶); Yang & Zhang (2006 ▶).

Experimental

Crystal data

[Zn(C8H9N2O4)2(H2O)2]·2C3H7NO

M = 641.94

Triclinic,

a = 7.3619 (9) Å

b = 9.3194 (13) Å

c = 11.2301 (15) Å

α = 76.281 (1)°

β = 87.621 (2)°

γ = 68.888 (1)°

V = 697.44 (16) Å3

Z = 1

Mo Kα radiation

μ = 0.95 mm−1

T = 298 K

0.43 × 0.28 × 0.25 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.685, T max = 0.797

3640 measured reflections

2425 independent reflections

2205 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.076

S = 1.06

2425 reflections

179 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022282/nc2185sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022282/nc2185Isup2.hkl

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

[Zn(C8H9N2O4)2(H2O)2]·2C3H7NO	Z = 1
Mr = 641.94	F(000) = 336
Triclinic, P1	Dx = 1.528 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3619 (9) Å	Cell parameters from 2051 reflections
b = 9.3194 (13) Å	θ = 2.5–23.9°
c = 11.2301 (15) Å	µ = 0.95 mm−1
α = 76.281 (1)°	T = 298 K
β = 87.621 (2)°	Block, colorless
γ = 68.888 (1)°	0.43 × 0.28 × 0.25 mm
V = 697.44 (16) Å3

Bruker SMART 1000 CCD area-detector diffractometer	2425 independent reflections
Radiation source: fine-focus sealed tube	2205 reflections with I > 2σ(I)
graphite	Rint = 0.015
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→8
Tmin = 0.685, Tmax = 0.797	k = −10→11
3640 measured reflections	l = −13→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H-atom parameters constrained
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0389P)2 + 0.2536P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2425 reflections	Δρmax = 0.26 e Å−3
179 parameters	Δρmin = −0.33 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.067 (4)

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	Occ. (<1)
Zn1	0.5000	0.5000	0.5000	0.02921 (14)
N1	0.6351 (2)	0.25671 (17)	0.54820 (14)	0.0248 (3)
N2	0.8023 (2)	0.00172 (18)	0.60587 (15)	0.0287 (4)
H1N1	0.8740	−0.0885	0.6506	0.034*
N3	0.1215 (3)	0.4911 (2)	0.86419 (18)	0.0419 (4)
O1	0.4380 (2)	0.43510 (15)	0.33379 (12)	0.0342 (3)
O2	0.49486 (10)	0.22669 (8)	0.25454 (6)	0.0384 (4)
H1O2	0.5591	0.1315	0.2727	0.058*	0.60
O3	0.68632 (10)	−0.06116 (8)	0.31714 (6)	0.0423 (4)
H1O3	0.6132	0.0311	0.2920	0.063*	0.40
O4	0.86310 (10)	−0.23869 (8)	0.47855 (6)	0.0412 (4)
O5	0.03879 (10)	0.74901 (8)	0.76828 (6)	0.0575 (5)
O6	0.77394 (10)	0.51222 (8)	0.43114 (6)	0.0381 (4)
H1O6	0.7938	0.5887	0.4435	0.057*
H2O6	0.8631	0.4310	0.4647	0.057*
C1	0.5133 (3)	0.2910 (2)	0.34026 (17)	0.0275 (4)
C2	0.6268 (3)	0.1875 (2)	0.45418 (17)	0.0240 (4)
C3	0.7305 (3)	0.0277 (2)	0.48902 (17)	0.0251 (4)
C4	0.7647 (3)	−0.1017 (2)	0.42490 (19)	0.0306 (4)
C5	0.7424 (3)	0.1403 (2)	0.63940 (17)	0.0272 (4)
C6	0.7850 (3)	0.1559 (2)	0.76285 (18)	0.0357 (5)
H6C	0.7435	0.2675	0.7620	0.043*
H6D	0.9247	0.1093	0.7807	0.043*
C7	0.6844 (4)	0.0768 (3)	0.8641 (2)	0.0553 (7)
H7A	0.5456	0.1187	0.8432	0.066*
H7B	0.7320	−0.0358	0.8679	0.066*
C8	0.7156 (4)	0.0996 (3)	0.9888 (2)	0.0571 (7)
H8B	0.7054	0.2071	0.9815	0.086*	0.60
H8C	0.8429	0.0289	1.0226	0.086*	0.60
H8A	0.6186	0.0775	1.0420	0.086*	0.60
H8E	0.8356	0.1177	0.9921	0.086*	0.40
H8D	0.7220	0.0065	1.0504	0.086*	0.40
H8F	0.6094	0.1893	1.0037	0.086*	0.40
C9	0.0112 (3)	0.6238 (3)	0.7883 (2)	0.0442 (6)
H9	−0.0947	0.6218	0.7473	0.053*
C10	0.2943 (4)	0.4853 (3)	0.9244 (3)	0.0616 (7)
H10A	0.4070	0.4350	0.8825	0.092*
H10B	0.3051	0.4261	1.0080	0.092*
H10C	0.2858	0.5910	0.9226	0.092*
C11	0.0897 (6)	0.3442 (3)	0.8741 (3)	0.0793 (10)
H11A	−0.0320	0.3659	0.8325	0.119*
H11B	0.0863	0.2947	0.9590	0.119*
H11C	0.1939	0.2747	0.8372	0.119*

	U11	U22	U33	U12	U13	U23
Zn1	0.0353 (2)	0.01589 (19)	0.0328 (2)	−0.00545 (13)	−0.00206 (13)	−0.00454 (13)
N1	0.0288 (8)	0.0178 (8)	0.0263 (8)	−0.0071 (6)	−0.0014 (6)	−0.0037 (6)
N2	0.0310 (8)	0.0161 (8)	0.0325 (9)	−0.0048 (7)	−0.0042 (7)	0.0012 (7)
N3	0.0475 (11)	0.0272 (10)	0.0455 (11)	−0.0102 (8)	0.0006 (9)	−0.0037 (8)
O1	0.0437 (8)	0.0194 (7)	0.0312 (8)	−0.0033 (6)	−0.0080 (6)	−0.0020 (6)
O2	0.0494 (9)	0.0298 (8)	0.0317 (8)	−0.0069 (7)	−0.0092 (6)	−0.0090 (6)
O3	0.0549 (9)	0.0284 (8)	0.0421 (9)	−0.0081 (7)	−0.0025 (7)	−0.0156 (7)
O4	0.0415 (8)	0.0192 (7)	0.0586 (10)	−0.0040 (6)	−0.0032 (7)	−0.0113 (7)
O5	0.0633 (11)	0.0276 (9)	0.0651 (12)	−0.0046 (8)	−0.0201 (9)	0.0046 (8)
O6	0.0358 (8)	0.0230 (7)	0.0548 (10)	−0.0097 (6)	0.0027 (7)	−0.0097 (7)
C1	0.0283 (10)	0.0239 (10)	0.0281 (10)	−0.0075 (8)	0.0003 (8)	−0.0050 (8)
C2	0.0248 (9)	0.0205 (9)	0.0264 (10)	−0.0081 (7)	0.0016 (7)	−0.0051 (7)
C3	0.0245 (9)	0.0199 (9)	0.0300 (10)	−0.0077 (7)	0.0017 (7)	−0.0045 (8)
C4	0.0285 (10)	0.0229 (10)	0.0410 (12)	−0.0089 (8)	0.0050 (9)	−0.0100 (9)
C5	0.0291 (10)	0.0199 (9)	0.0296 (10)	−0.0079 (8)	−0.0023 (8)	−0.0011 (7)
C6	0.0445 (12)	0.0277 (11)	0.0320 (11)	−0.0117 (9)	−0.0089 (9)	−0.0020 (8)
C7	0.0699 (17)	0.0634 (17)	0.0420 (14)	−0.0321 (14)	0.0123 (12)	−0.0188 (12)
C8	0.0653 (17)	0.0591 (17)	0.0402 (14)	−0.0146 (14)	0.0039 (12)	−0.0123 (12)
C9	0.0379 (12)	0.0437 (14)	0.0437 (13)	−0.0057 (10)	−0.0053 (10)	−0.0099 (11)
C10	0.0469 (14)	0.0528 (16)	0.0639 (18)	−0.0051 (12)	−0.0138 (13)	0.0076 (13)
C11	0.113 (3)	0.0437 (17)	0.089 (2)	−0.0384 (18)	0.014 (2)	−0.0156 (16)

Zn1—N1	2.0643 (15)	C1—C2	1.479 (3)
Zn1—N1i	2.0643 (15)	C2—C3	1.372 (3)
Zn1—O6i	2.1616	C3—C4	1.488 (3)
Zn1—O6	2.1616	C5—C6	1.485 (3)
Zn1—O1	2.2053 (14)	C6—C7	1.520 (3)
Zn1—O1i	2.2053 (14)	C6—H6C	0.9700
N1—C5	1.331 (2)	C6—H6D	0.9700
N1—C2	1.375 (2)	C7—C8	1.505 (3)
N2—C5	1.346 (2)	C7—H7A	0.9700
N2—C3	1.369 (2)	C7—H7B	0.9700
N2—H1N1	0.8600	C8—H8B	0.9600
N3—C9	1.322 (3)	C8—H8C	0.9600
N3—C10	1.443 (3)	C8—H8A	0.9600
N3—C11	1.448 (3)	C8—H8E	0.9602
O1—C1	1.240 (2)	C8—H8D	0.9601
O2—C1	1.284 (2)	C8—H8F	0.9602
O2—H1O2	0.8200	C9—H9	0.9300
O3—C4	1.274 (2)	C10—H10A	0.9600
O3—H1O3	0.8200	C10—H10B	0.9600
O4—C4	1.234 (2)	C10—H10C	0.9600
O5—C9	1.223 (3)	C11—H11A	0.9600
O6—H1O6	0.8201	C11—H11B	0.9600
O6—H2O6	0.8200	C11—H11C	0.9600
N1—Zn1—N1i	180.0	O3—C4—C3	116.34 (16)
N1—Zn1—O6i	92.14 (5)	N1—C5—N2	110.03 (17)
N1i—Zn1—O6i	87.86 (5)	N1—C5—C6	126.12 (17)
N1—Zn1—O6	87.86 (5)	N2—C5—C6	123.80 (17)
N1i—Zn1—O6	92.14 (5)	C5—C6—C7	113.04 (18)
O6i—Zn1—O6	180.0	C5—C6—H6C	109.0
N1—Zn1—O1	78.58 (5)	C7—C6—H6C	109.0
N1i—Zn1—O1	101.43 (5)	C5—C6—H6D	109.0
O6i—Zn1—O1	88.98 (4)	C7—C6—H6D	109.0
O6—Zn1—O1	91.02 (4)	H6C—C6—H6D	107.8
N1—Zn1—O1i	101.43 (5)	C8—C7—C6	113.9 (2)
N1i—Zn1—O1i	78.57 (5)	C8—C7—H7A	108.8
O6i—Zn1—O1i	91.02 (4)	C6—C7—H7A	108.8
O6—Zn1—O1i	88.98 (4)	C8—C7—H7B	108.8
O1—Zn1—O1i	180.0	C6—C7—H7B	108.8
C5—N1—C2	106.21 (15)	H7A—C7—H7B	107.7
C5—N1—Zn1	141.02 (13)	C7—C8—H8B	109.5
C2—N1—Zn1	112.56 (12)	C7—C8—H8C	109.5
C5—N2—C3	108.91 (16)	C7—C8—H8A	109.5
C5—N2—H1N1	125.5	C7—C8—H8E	109.5
C3—N2—H1N1	125.5	C7—C8—H8D	109.5
C9—N3—C10	119.9 (2)	H8E—C8—H8D	109.5
C9—N3—C11	121.1 (2)	C7—C8—H8F	109.5
C10—N3—C11	118.4 (2)	H8E—C8—H8F	109.5
C1—O1—Zn1	112.88 (12)	H8D—C8—H8F	109.5
C1—O2—H1O2	110.3	O5—C9—N3	124.6 (2)
C4—O3—H1O3	117.8	O5—C9—H9	117.7
Zn1—O6—H1O6	112.3	N3—C9—H9	117.7
Zn1—O6—H2O6	109.2	N3—C10—H10A	109.5
H1O6—O6—H2O6	108.9	N3—C10—H10B	109.5
O1—C1—O2	123.54 (16)	H10A—C10—H10B	109.5
O1—C1—C2	118.08 (17)	N3—C10—H10C	109.5
O2—C1—C2	118.37 (16)	H10A—C10—H10C	109.5
C3—C2—N1	109.67 (16)	H10B—C10—H10C	109.5
C3—C2—C1	132.62 (17)	N3—C11—H11A	109.5
N1—C2—C1	117.71 (16)	N3—C11—H11B	109.5
N2—C3—C2	105.17 (16)	H11A—C11—H11B	109.5
N2—C3—C4	122.91 (17)	N3—C11—H11C	109.5
C2—C3—C4	131.90 (18)	H11A—C11—H11C	109.5
O4—C4—O3	124.73 (17)	H11B—C11—H11C	109.5
O4—C4—C3	118.93 (18)
N1i—Zn1—N1—C5	23 (100)	O1—C1—C2—N1	2.6 (3)
O6i—Zn1—N1—C5	−94.0 (2)	O2—C1—C2—N1	−175.99 (15)
O6—Zn1—N1—C5	86.0 (2)	C5—N2—C3—C2	0.5 (2)
O1—Zn1—N1—C5	177.5 (2)	C5—N2—C3—C4	−178.27 (17)
O1i—Zn1—N1—C5	−2.5 (2)	N1—C2—C3—N2	−0.2 (2)
N1i—Zn1—N1—C2	−151 (100)	C1—C2—C3—N2	−179.58 (19)
O6i—Zn1—N1—C2	92.28 (12)	N1—C2—C3—C4	178.35 (18)
O6—Zn1—N1—C2	−87.72 (12)	C1—C2—C3—C4	−1.0 (4)
O1—Zn1—N1—C2	3.76 (12)	N2—C3—C4—O4	−0.5 (3)
O1i—Zn1—N1—C2	−176.24 (12)	C2—C3—C4—O4	−178.83 (17)
N1—Zn1—O1—C1	−2.53 (13)	N2—C3—C4—O3	178.75 (15)
N1i—Zn1—O1—C1	177.47 (13)	C2—C3—C4—O3	0.4 (3)
O6i—Zn1—O1—C1	−94.92 (13)	C2—N1—C5—N2	0.4 (2)
O6—Zn1—O1—C1	85.08 (13)	Zn1—N1—C5—N2	−173.60 (14)
O1i—Zn1—O1—C1	168 (100)	C2—N1—C5—C6	−177.05 (18)
Zn1—O1—C1—O2	179.33 (13)	Zn1—N1—C5—C6	8.9 (3)
Zn1—O1—C1—C2	0.8 (2)	C3—N2—C5—N1	−0.6 (2)
C5—N1—C2—C3	−0.1 (2)	C3—N2—C5—C6	176.97 (17)
Zn1—N1—C2—C3	175.82 (12)	N1—C5—C6—C7	110.5 (2)
C5—N1—C2—C1	179.37 (16)	N2—C5—C6—C7	−66.6 (3)
Zn1—N1—C2—C1	−4.7 (2)	C5—C6—C7—C8	−176.5 (2)
O1—C1—C2—C3	−178.04 (19)	C10—N3—C9—O5	−3.7 (4)
O2—C1—C2—C3	3.3 (3)	C11—N3—C9—O5	−174.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H2O6···O4ii	0.82	2.16	2.9594 (14)	167
O6—H1O6···O4iii	0.82	1.98	2.796	175
O3—H1O3···O2	0.82	1.67	2.478	169
O2—H1O2···O3	0.82	1.66	2.478	177
N2—H1N1···O5iv	0.86	1.84	2.6789 (17)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H2O6⋯O4i	0.82	2.16	2.9594 (14)	167
O6—H1O6⋯O4ii	0.82	1.98	2.796	175
O3—H1O3⋯O2	0.82	1.67	2.478	169
O2—H1O2⋯O3	0.82	1.66	2.478	177
N2—H1N1⋯O5iii	0.86	1.84	2.6789 (17)	166

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