2-Amino-pyrimidinium 4-hy-droxy-pyridinium-2,6-dicarboxyl-ate monohydrate.

In the crystal structure of the title compound, C(4)H(6)N(3) (+)·C(7)H(4)NO(5) (-)·H(2)O, inter-molecular N-H⋯N, N-H⋯O and O-H⋯O hydrogen bonds link the cations and anions into almost planar sheets parallel to (102). These hydrogen-bonded sheets are packed into the crystal with the formation of centrosymmetric voids of 68 Å(3), which are filled by the water mol-ecules, each of which is disordered over four positions.

Related literature

For related structures, see: Aghabozorg et al. (2008 ▶); Moghimi et al. (2005 ▶); Hall et al. (2000 ▶); Lynch & Jones (2004 ▶); Eshtiagh-Hosseini et al. (2010 ▶); Smith et al. (2006a ▶,b ▶). For hydrogen bonding, see: Desiraju (1989 ▶).

Experimental

Crystal data

C4H6N3 +·C7H4NO5 −·H2O

M = 296.25

Monoclinic,

a = 17.822 (2) Å

b = 12.2233 (14) Å

c = 12.0676 (14) Å

β = 103.345 (2)°

V = 2557.8 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 100 K

0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.970, T max = 0.983

14881 measured reflections

3383 independent reflections

2703 reflections with I > 2/s(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.134

S = 0.90

3383 reflections

203 parameters

13 restraints

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810029533/cv2745sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029533/cv2745Isup2.hkl

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

C4H6N3+·C7H4NO5−·H2O	F(000) = 1232
Mr = 296.25	Dx = 1.539 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2135 reflections
a = 17.822 (2) Å	θ = 3–30°
b = 12.2233 (14) Å	µ = 0.13 mm−1
c = 12.0676 (14) Å	T = 100 K
β = 103.345 (2)°	Prism, colourless
V = 2557.8 (5) Å3	0.20 × 0.20 × 0.15 mm
Z = 8

Bruker SMART APEXII CCD area detector diffractometer	3383 independent reflections
Radiation source: fine-focus sealed tube	2703 reflections with I > 2/s(I)
graphite	Rint = 0.031
phi and ω scans	θmax = 29.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −24→24
Tmin = 0.970, Tmax = 0.983	k = −16→16
14881 measured reflections	l = −16→16

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)] = 0.046	Hydrogen site location: mixed
wR(F2) = 0.134	H-atom parameters constrained
S = 0.90	w = 1/[σ2(Fo2) + (0.0847P)2 + 2.9446P] where P = (Fo2 + 2Fc2)/3
3383 reflections	(Δ/σ)max = 0.002
203 parameters	Δρmax = 0.45 e Å−3
13 restraints	Δρmin = −0.33 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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)
N1	1.14962 (8)	−0.04289 (11)	0.20255 (13)	0.0224 (3)
H1N	1.1618	0.0308	0.2020	0.027*
O1	1.04750 (7)	0.11863 (10)	0.14699 (12)	0.0282 (3)
O2	0.94910 (7)	−0.00108 (11)	0.09859 (11)	0.0285 (3)
O3	1.08809 (7)	−0.36262 (10)	0.17357 (11)	0.0255 (3)
H3O	1.1310	−0.4104	0.1904	0.031*
O4	1.29127 (7)	0.02724 (11)	0.27479 (14)	0.0350 (4)
O5	1.33747 (7)	−0.14137 (11)	0.32416 (14)	0.0373 (4)
C1	1.01849 (10)	0.02443 (14)	0.13234 (15)	0.0239 (3)
C2	1.07491 (9)	−0.06993 (14)	0.16221 (14)	0.0208 (3)
C3	1.05349 (9)	−0.17748 (14)	0.15300 (13)	0.0197 (3)
H3A	1.0009	−0.1967	0.1244	0.024*
C4	1.10958 (9)	−0.25973 (13)	0.18601 (14)	0.0197 (3)
C5	1.18672 (9)	−0.22748 (13)	0.23042 (14)	0.0207 (3)
H5A	1.2257	−0.2810	0.2551	0.025*
C6	1.20497 (9)	−0.11862 (13)	0.23764 (15)	0.0222 (3)
C7	1.28608 (10)	−0.07533 (15)	0.28376 (17)	0.0290 (4)
N2	0.82237 (8)	0.35778 (12)	0.04751 (13)	0.0223 (3)
N3	0.94887 (8)	0.28765 (12)	0.10759 (12)	0.0206 (3)
H3N	0.9807	0.2273	0.1274	0.025*
N4	0.84352 (8)	0.17156 (12)	0.06968 (13)	0.0233 (3)
H4NA	0.8755	0.1131	0.0843	0.028*
H4NB	0.7931	0.1639	0.0425	0.028*
C8	0.87116 (9)	0.27213 (13)	0.07514 (14)	0.0194 (3)
C9	0.85244 (10)	0.45737 (14)	0.05743 (15)	0.0244 (4)
H9A	0.8184	0.5180	0.0396	0.029*
C10	0.93171 (10)	0.47828 (14)	0.09281 (15)	0.0247 (4)
H10A	0.9515	0.5508	0.1004	0.030*
C11	0.97917 (9)	0.38928 (15)	0.11582 (14)	0.0227 (3)
H11A	1.0335	0.3990	0.1376	0.027*
O1W	0.8160 (2)	0.8577 (4)	−0.0224 (4)	0.0257 (5)	0.292 (3)
H1WA	0.8468	0.8115	0.0198	0.031*	0.292 (3)
H1WB	0.8055	0.9096	0.0223	0.031*	0.292 (3)
O2W	0.8104 (3)	0.9291 (4)	0.0129 (4)	0.0257 (5)	0.249 (3)
H2WA	0.8544	0.9496	0.0513	0.031*	0.249 (3)
H2WB	0.8178	0.8757	−0.0286	0.031*	0.249 (3)
O3W	0.8024 (3)	0.7046 (4)	0.0112 (5)	0.0257 (5)	0.236 (3)
H3WA	0.8188	0.7058	−0.0496	0.031*	0.236 (3)
H3WB	0.7571	0.6781	−0.0054	0.031*	0.236 (3)
O4W	0.8561 (3)	0.7918 (5)	0.0081 (5)	0.0257 (5)	0.224 (3)
H4WA	0.8132	0.8099	−0.0354	0.031*	0.224 (3)
H4WB	0.8853	0.8478	0.0157	0.031*	0.224 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0147 (6)	0.0179 (6)	0.0343 (8)	0.0014 (5)	0.0046 (5)	−0.0010 (5)
O1	0.0217 (6)	0.0226 (6)	0.0404 (7)	0.0071 (5)	0.0073 (5)	0.0056 (5)
O2	0.0163 (6)	0.0317 (7)	0.0376 (7)	0.0079 (5)	0.0064 (5)	0.0096 (5)
O3	0.0164 (5)	0.0187 (6)	0.0386 (7)	−0.0016 (4)	0.0010 (5)	0.0032 (5)
O4	0.0188 (6)	0.0212 (6)	0.0616 (9)	−0.0020 (5)	0.0024 (6)	−0.0111 (6)
O5	0.0145 (6)	0.0261 (7)	0.0649 (10)	0.0030 (5)	−0.0041 (6)	−0.0122 (6)
C1	0.0192 (8)	0.0243 (8)	0.0292 (8)	0.0072 (6)	0.0077 (6)	0.0066 (6)
C2	0.0144 (7)	0.0233 (8)	0.0245 (8)	0.0042 (6)	0.0041 (6)	0.0023 (6)
C3	0.0127 (7)	0.0233 (8)	0.0223 (7)	0.0006 (6)	0.0027 (5)	0.0014 (6)
C4	0.0156 (7)	0.0211 (7)	0.0218 (7)	−0.0011 (6)	0.0031 (6)	0.0014 (6)
C5	0.0139 (7)	0.0195 (7)	0.0270 (8)	0.0024 (5)	0.0010 (6)	−0.0010 (6)
C6	0.0132 (7)	0.0208 (7)	0.0311 (8)	0.0021 (6)	0.0018 (6)	−0.0039 (6)
C7	0.0151 (7)	0.0234 (8)	0.0460 (11)	−0.0010 (6)	0.0020 (7)	−0.0125 (7)
N2	0.0139 (6)	0.0213 (7)	0.0301 (7)	0.0010 (5)	0.0018 (5)	0.0020 (5)
N3	0.0112 (6)	0.0252 (7)	0.0235 (7)	0.0014 (5)	0.0001 (5)	0.0016 (5)
N4	0.0119 (6)	0.0206 (7)	0.0351 (8)	0.0015 (5)	0.0008 (5)	0.0035 (6)
C8	0.0128 (7)	0.0220 (7)	0.0220 (7)	0.0010 (5)	0.0015 (6)	0.0017 (6)
C9	0.0179 (8)	0.0225 (8)	0.0314 (9)	0.0018 (6)	0.0025 (6)	0.0023 (6)
C10	0.0189 (8)	0.0244 (8)	0.0297 (8)	−0.0034 (6)	0.0031 (6)	0.0002 (6)
C11	0.0139 (7)	0.0298 (8)	0.0231 (8)	−0.0037 (6)	0.0015 (6)	0.0003 (6)
O1W	0.0201 (11)	0.0265 (12)	0.0296 (13)	−0.0109 (9)	0.0042 (9)	−0.0058 (10)
O2W	0.0201 (11)	0.0265 (12)	0.0296 (13)	−0.0109 (9)	0.0042 (9)	−0.0058 (10)
O3W	0.0201 (11)	0.0265 (12)	0.0296 (13)	−0.0109 (9)	0.0042 (9)	−0.0058 (10)
O4W	0.0201 (11)	0.0265 (12)	0.0296 (13)	−0.0109 (9)	0.0042 (9)	−0.0058 (10)

N1—C6	1.348 (2)	N3—C11	1.349 (2)
N1—C2	1.349 (2)	N3—C8	1.363 (2)
N1—H1N	0.9263	N3—H3N	0.9273
O1—C1	1.258 (2)	N4—C8	1.320 (2)
O2—C1	1.249 (2)	N4—H4NA	0.9056
O3—C4	1.3131 (19)	N4—H4NB	0.8882
O3—H3O	0.9466	C9—C10	1.402 (2)
O4—C7	1.264 (2)	C9—H9A	0.9500
O5—C7	1.234 (2)	C10—C11	1.367 (2)
C1—C2	1.518 (2)	C10—H10A	0.9500
C2—C3	1.366 (2)	C11—H11A	0.9500
C3—C4	1.409 (2)	O1W—H1WA	0.8664
C3—H3A	0.9500	O1W—H1WB	0.8805
C4—C5	1.411 (2)	O2W—H2WA	0.8508
C5—C6	1.368 (2)	O2W—H2WB	0.8509
C5—H5A	0.9500	O3W—H3WA	0.8500
C6—C7	1.519 (2)	O3W—H3WB	0.8501
N2—C9	1.324 (2)	O4W—H4WA	0.8501
N2—C8	1.353 (2)	O4W—H4WB	0.8523
C6—N1—C2	122.33 (15)	O4—C7—C6	113.36 (15)
C6—N1—H1N	121.0	C9—N2—C8	117.74 (14)
C2—N1—H1N	116.7	C11—N3—C8	120.82 (14)
C4—O3—H3O	111.5	C11—N3—H3N	120.2
O2—C1—O1	128.19 (15)	C8—N3—H3N	119.0
O2—C1—C2	116.07 (15)	C8—N4—H4NA	121.0
O1—C1—C2	115.72 (15)	C8—N4—H4NB	116.8
N1—C2—C3	119.94 (14)	H4NA—N4—H4NB	121.7
N1—C2—C1	116.36 (15)	N4—C8—N2	119.81 (14)
C3—C2—C1	123.68 (14)	N4—C8—N3	119.12 (14)
C2—C3—C4	119.80 (14)	N2—C8—N3	121.07 (15)
C2—C3—H3A	120.1	N2—C9—C10	123.61 (15)
C4—C3—H3A	120.1	N2—C9—H9A	118.2
O3—C4—C3	118.81 (14)	C10—C9—H9A	118.2
O3—C4—C5	122.94 (14)	C11—C10—C9	116.72 (16)
C3—C4—C5	118.25 (15)	C11—C10—H10A	121.6
C6—C5—C4	119.49 (14)	C9—C10—H10A	121.6
C6—C5—H5A	120.3	N3—C11—C10	119.98 (15)
C4—C5—H5A	120.3	N3—C11—H11A	120.0
N1—C6—C5	120.14 (15)	C10—C11—H11A	120.0
N1—C6—C7	116.19 (15)	H1WA—O1W—H1WB	107.7
C5—C6—C7	123.67 (14)	H2WA—O2W—H2WB	107.3
O5—C7—O4	128.37 (16)	H3WA—O3W—H3WB	107.4
O5—C7—C6	118.28 (16)	H4WA—O4W—H4WB	107.2
C6—N1—C2—C3	−1.8 (3)	C4—C5—C6—N1	0.0 (3)
C6—N1—C2—C1	176.57 (15)	C4—C5—C6—C7	−179.86 (16)
O2—C1—C2—N1	−177.73 (15)	N1—C6—C7—O5	175.00 (18)
O1—C1—C2—N1	0.9 (2)	C5—C6—C7—O5	−5.1 (3)
O2—C1—C2—C3	0.5 (2)	N1—C6—C7—O4	−5.0 (2)
O1—C1—C2—C3	179.14 (16)	C5—C6—C7—O4	174.86 (17)
N1—C2—C3—C4	0.2 (2)	C9—N2—C8—N4	178.06 (16)
C1—C2—C3—C4	−178.04 (15)	C9—N2—C8—N3	−2.6 (2)
C2—C3—C4—O3	−178.17 (15)	C11—N3—C8—N4	−178.99 (15)
C2—C3—C4—C5	1.4 (2)	C11—N3—C8—N2	1.7 (2)
O3—C4—C5—C6	178.07 (16)	C8—N2—C9—C10	1.2 (3)
C3—C4—C5—C6	−1.5 (2)	N2—C9—C10—C11	1.2 (3)
C2—N1—C6—C5	1.7 (3)	C8—N3—C11—C10	0.8 (2)
C2—N1—C6—C7	−178.45 (16)	C9—C10—C11—N3	−2.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4NA···O2	0.91	1.90	2.795 (2)	172
N1—H1N···O1	0.93	2.26	2.6639 (19)	105
N1—H1N···O4	0.93	2.27	2.618 (2)	101
N4—H4NB···N2i	0.89	2.11	2.990 (2)	171
N3—H3N···O1	0.93	1.76	2.683 (2)	171
O3—H3O···O4ii	0.95	1.55	2.4910 (19)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4NA⋯O2	0.91	1.90	2.795 (2)	172
N4—H4NB⋯N2i	0.89	2.11	2.990 (2)	171
N3—H3N⋯O1	0.93	1.76	2.683 (2)	171
O3—H3O⋯O4ii	0.95	1.55	2.4910 (19)	171

Symmetry codes: (i) ; (ii) .