2-Amino-1-(2-carboxyl-atoeth-yl)pyrimidin-1-ium monohydrate.

In the title structure, C(7)H(9)N(3)O(2)·H(2)O, there are two formula units in the asymmetric unit. The mol-ecule is a zwitterion, containing a quaternary N atom and a deprotonated carboxyl group, with C-O distances in the range 1.256 (2)-1.266 (3) Å. The two independent mol-ecules form a hydrogen-bonded R(2) (2)(16) dimer about an approximate inversion center via N-H⋯O hydrogen bonds, with N⋯O distances of 2.766 (2) and 2.888 (2) Å. O-H⋯O hydro-gen bonds involving the water mol-ecules and additional N-H⋯O hydrogen bonds link these dimers, forming double chains.

Related literature

For background information on deep eutectic solvents, see: Abbott et al. (2003 ▶, 2004 ▶); Reddy (2006 ▶); Santos et al. (2007 ▶); Walker et al. (2004 ▶). For graph sets, see: Etter (1990 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For related structures, see: Holy et al. (1999 ▶); Slouf et al. (2002 ▶).

Experimental

Crystal data

C7H9N3O2·n class="Chemical">H2O

M = 185.19

Monoclinic,

a = 10.075 (2) Å

b = 15.576 (5) Å

c = 10.810 (3) Å

β = 107.741 (16)°

V = 1615.7 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 90 K

0.17 × 0.12 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer with Oxford Cryostream cooler

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.980, T max = 0.994

10202 measured reflections

3518 independent reflections

2418 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.119

S = 1.02

3518 reflections

260 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.34 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045332/pv2345sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045332/pv2345Isup2.hkl

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

C7H9N3O2·H2O	F(000) = 784
Mr = 185.19	Dx = 1.523 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3071 reflections
a = 10.075 (2) Å	θ = 2.5–27.1°
b = 15.576 (5) Å	µ = 0.12 mm−1
c = 10.810 (3) Å	T = 90 K
β = 107.741 (16)°	Plate, colorless
V = 1615.7 (8) Å3	0.17 × 0.12 × 0.05 mm
Z = 8

Nonius KappaCCD diffractometer with Oxford Cryostream cooler	3518 independent reflections
Radiation source: fine-focus sealed tube	2418 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω and φ scans	θmax = 27.1°, θmin = 2.7°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −12→12
Tmin = 0.980, Tmax = 0.994	k = −19→16
10202 measured reflections	l = −13→13

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0416P)2 + 1.0034P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3518 reflections	Δρmax = 0.26 e Å−3
260 parameters	Δρmin = −0.34 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0052 (10)

Experimental. 1H (D2O): δ(p.p.m.) 2.72 (t, 2H, J = 6.14 Hz), 4.33 (t, 2H, J = 6.14 Hz), 7.01 (t, 1H, J = 5.6 Hz), 8.32 (d, 1H, J = 5.6 Hz), and 8.69 (d, 1H, J = 5.6 Hz). 13C (D2O): δ(p.p.m.) 34.2, 51.9, 111.3, 150.5, 155.8, 166.2, and 177.5. IR (thin film, KBr plates, cm-1): 3428.76 (m, br), 3093.35 (br), 2363.8 (m), 1675.0 (m), 1386.82 (s), 1262.48 (s), 1193.82 (w, sh), 1094.27 (w), 1024.62 (w), and 931.94 (w, sh).

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
O1	0.16601 (14)	0.69376 (10)	0.15055 (14)	0.0176 (4)
O2	0.30612 (14)	0.78552 (10)	0.28952 (15)	0.0188 (4)
N1	−0.14185 (16)	0.70633 (11)	0.33727 (16)	0.0135 (4)
N2	−0.23793 (17)	0.66797 (12)	0.50401 (18)	0.0161 (4)
N3	−0.02988 (18)	0.60908 (12)	0.50172 (19)	0.0159 (4)
H31N	−0.036 (2)	0.5803 (16)	0.566 (2)	0.019*
H32N	0.038 (2)	0.5978 (15)	0.464 (2)	0.019*
C1	−0.1350 (2)	0.66116 (13)	0.4473 (2)	0.0134 (4)
C2	−0.3421 (2)	0.72143 (14)	0.4525 (2)	0.0152 (5)
H2	−0.4151	0.7250	0.4909	0.018*
C3	−0.3504 (2)	0.77295 (14)	0.3446 (2)	0.0159 (5)
H3	−0.4249	0.8122	0.3112	0.019*
C4	−0.2464 (2)	0.76392 (14)	0.2900 (2)	0.0161 (5)
H4	−0.2467	0.7985	0.2175	0.019*
C5	−0.0369 (2)	0.69512 (14)	0.2672 (2)	0.0143 (5)
H5A	−0.0817	0.7058	0.1734	0.017*
H5B	−0.0029	0.6351	0.2774	0.017*
C6	0.0857 (2)	0.75559 (14)	0.3174 (2)	0.0164 (5)
H6A	0.1298	0.7452	0.4113	0.020*
H6B	0.0516	0.8156	0.3065	0.020*
C7	0.1944 (2)	0.74413 (14)	0.2470 (2)	0.0142 (5)
O3	0.20974 (14)	0.56176 (10)	0.42323 (14)	0.0169 (3)
O4	0.07476 (14)	0.47312 (10)	0.27549 (14)	0.0175 (4)
N4	0.51826 (16)	0.56177 (11)	0.22871 (16)	0.0132 (4)
N5	0.58362 (17)	0.58906 (12)	0.03946 (17)	0.0159 (4)
N6	0.37231 (18)	0.63627 (12)	0.05084 (19)	0.0161 (4)
H61N	0.362 (2)	0.6558 (16)	−0.025 (3)	0.019*
H62N	0.313 (2)	0.6537 (15)	0.094 (2)	0.019*
C8	0.4900 (2)	0.59599 (13)	0.1067 (2)	0.0137 (4)
C9	0.7023 (2)	0.54856 (14)	0.0946 (2)	0.0164 (5)
H9	0.7685	0.5450	0.0483	0.020*
C10	0.7352 (2)	0.51078 (14)	0.2174 (2)	0.0172 (5)
H10	0.8202	0.4807	0.2535	0.021*
C11	0.6406 (2)	0.51888 (14)	0.2830 (2)	0.0169 (5)
H11	0.6595	0.4946	0.3672	0.020*
C12	0.4179 (2)	0.56957 (14)	0.3045 (2)	0.0140 (5)
H12A	0.3793	0.6285	0.2953	0.017*
H12B	0.4672	0.5594	0.3976	0.017*
C13	0.2994 (2)	0.50517 (14)	0.2575 (2)	0.0171 (5)
H13A	0.3384	0.4464	0.2729	0.021*
H13B	0.2565	0.5123	0.1627	0.021*
C14	0.1859 (2)	0.51433 (14)	0.3239 (2)	0.0144 (5)
O1W	0.42213 (16)	0.65900 (11)	0.59146 (17)	0.0215 (4)
H11W	0.359 (3)	0.6329 (17)	0.527 (3)	0.032*
H12W	0.384 (3)	0.6801 (18)	0.643 (3)	0.032*
O2W	−0.06112 (17)	0.60258 (12)	−0.02453 (18)	0.0270 (4)
H21W	0.023 (3)	0.6207 (18)	0.026 (3)	0.040*
H22W	−0.043 (3)	0.5764 (19)	−0.088 (3)	0.040*

	U11	U22	U33	U12	U13	U23
O1	0.0148 (7)	0.0222 (9)	0.0171 (8)	0.0004 (6)	0.0067 (6)	−0.0044 (7)
O2	0.0152 (7)	0.0226 (9)	0.0200 (9)	−0.0030 (6)	0.0072 (6)	−0.0027 (7)
N1	0.0126 (8)	0.0152 (9)	0.0133 (10)	0.0016 (7)	0.0050 (7)	0.0000 (8)
N2	0.0147 (8)	0.0181 (10)	0.0170 (10)	−0.0001 (7)	0.0070 (7)	−0.0013 (8)
N3	0.0152 (9)	0.0178 (10)	0.0164 (10)	0.0020 (8)	0.0073 (8)	0.0037 (8)
C1	0.0138 (9)	0.0130 (11)	0.0136 (11)	−0.0026 (8)	0.0044 (8)	−0.0024 (9)
C2	0.0116 (9)	0.0182 (12)	0.0169 (12)	−0.0017 (9)	0.0061 (9)	−0.0049 (9)
C3	0.0129 (10)	0.0168 (12)	0.0177 (12)	0.0018 (8)	0.0042 (9)	0.0004 (9)
C4	0.0167 (10)	0.0168 (12)	0.0137 (12)	0.0002 (9)	0.0030 (9)	−0.0010 (9)
C5	0.0145 (10)	0.0168 (11)	0.0138 (11)	0.0016 (9)	0.0073 (8)	0.0005 (9)
C6	0.0153 (10)	0.0163 (12)	0.0186 (12)	−0.0011 (9)	0.0065 (9)	−0.0016 (9)
C7	0.0158 (10)	0.0150 (11)	0.0127 (11)	0.0019 (9)	0.0056 (9)	0.0047 (9)
O3	0.0154 (7)	0.0205 (8)	0.0159 (8)	0.0005 (6)	0.0063 (6)	−0.0019 (7)
O4	0.0141 (7)	0.0216 (9)	0.0168 (8)	−0.0026 (6)	0.0050 (6)	0.0005 (7)
N4	0.0123 (8)	0.0142 (9)	0.0143 (9)	0.0001 (7)	0.0057 (7)	0.0010 (7)
N5	0.0156 (8)	0.0172 (10)	0.0167 (10)	−0.0018 (7)	0.0077 (7)	−0.0012 (8)
N6	0.0170 (9)	0.0196 (10)	0.0135 (10)	0.0025 (8)	0.0074 (8)	0.0011 (8)
C8	0.0138 (9)	0.0118 (11)	0.0163 (11)	−0.0029 (8)	0.0059 (8)	−0.0019 (9)
C9	0.0134 (10)	0.0187 (12)	0.0183 (12)	−0.0029 (9)	0.0068 (9)	−0.0050 (10)
C10	0.0134 (10)	0.0169 (12)	0.0202 (12)	0.0003 (9)	0.0037 (9)	−0.0025 (9)
C11	0.0149 (10)	0.0168 (12)	0.0180 (12)	−0.0019 (9)	0.0035 (9)	−0.0010 (9)
C12	0.0146 (10)	0.0174 (12)	0.0116 (11)	0.0001 (8)	0.0064 (8)	−0.0013 (9)
C13	0.0178 (10)	0.0161 (11)	0.0190 (12)	−0.0009 (9)	0.0080 (9)	−0.0032 (9)
C14	0.0141 (10)	0.0168 (12)	0.0132 (11)	0.0020 (9)	0.0055 (8)	0.0040 (9)
O1W	0.0201 (8)	0.0266 (10)	0.0194 (9)	−0.0030 (7)	0.0083 (7)	−0.0066 (7)
O2W	0.0221 (8)	0.0396 (11)	0.0215 (10)	−0.0092 (8)	0.0100 (7)	−0.0071 (8)

O1—C7	1.266 (3)	N4—C11	1.367 (3)
O2—C7	1.256 (2)	N4—C8	1.370 (3)
N1—C4	1.359 (3)	N4—C12	1.487 (2)
N1—C1	1.365 (3)	N5—C9	1.322 (3)
N1—C5	1.487 (3)	N5—C8	1.359 (3)
N2—C2	1.322 (3)	N6—C8	1.315 (3)
N2—C1	1.360 (3)	N6—H61N	0.85 (3)
N3—C1	1.322 (3)	N6—H62N	0.90 (2)
N3—H31N	0.85 (3)	C9—C10	1.397 (3)
N3—H32N	0.91 (2)	C9—H9	0.9500
C2—C3	1.397 (3)	C10—C11	1.356 (3)
C2—H2	0.9500	C10—H10	0.9500
C3—C4	1.358 (3)	C11—H11	0.9500
C3—H3	0.9500	C12—C13	1.523 (3)
C4—H4	0.9500	C12—H12A	0.9900
C5—C6	1.516 (3)	C12—H12B	0.9900
C5—H5A	0.9900	C13—C14	1.531 (3)
C5—H5B	0.9900	C13—H13A	0.9900
C6—C7	1.522 (3)	C13—H13B	0.9900
C6—H6A	0.9900	O1W—H11W	0.89 (3)
C6—H6B	0.9900	O1W—H12W	0.84 (3)
O3—C14	1.265 (3)	O2W—H21W	0.90 (3)
O4—C14	1.258 (2)	O2W—H22W	0.86 (3)
C4—N1—C1	119.69 (17)	C11—N4—C12	118.61 (17)
C4—N1—C5	118.41 (17)	C8—N4—C12	121.46 (16)
C1—N1—C5	121.90 (17)	C9—N5—C8	118.44 (19)
C2—N2—C1	118.38 (19)	C8—N6—H61N	116.1 (16)
C1—N3—H31N	116.4 (16)	C8—N6—H62N	123.7 (15)
C1—N3—H32N	121.7 (15)	H61N—N6—H62N	119 (2)
H31N—N3—H32N	121 (2)	N6—C8—N5	117.9 (2)
N3—C1—N2	117.7 (2)	N6—C8—N4	121.43 (18)
N3—C1—N1	121.68 (18)	N5—C8—N4	120.66 (18)
N2—C1—N1	120.64 (18)	N5—C9—C10	123.34 (19)
N2—C2—C3	123.45 (19)	N5—C9—H9	118.3
N2—C2—H2	118.3	C10—C9—H9	118.3
C3—C2—H2	118.3	C11—C10—C9	117.2 (2)
C4—C3—C2	116.5 (2)	C11—C10—H10	121.4
C4—C3—H3	121.8	C9—C10—H10	121.4
C2—C3—H3	121.8	C10—C11—N4	120.4 (2)
C3—C4—N1	121.1 (2)	C10—C11—H11	119.8
C3—C4—H4	119.4	N4—C11—H11	119.8
N1—C4—H4	119.4	N4—C12—C13	110.99 (17)
N1—C5—C6	111.90 (17)	N4—C12—H12A	109.4
N1—C5—H5A	109.2	C13—C12—H12A	109.4
C6—C5—H5A	109.2	N4—C12—H12B	109.4
N1—C5—H5B	109.2	C13—C12—H12B	109.4
C6—C5—H5B	109.2	H12A—C12—H12B	108.0
H5A—C5—H5B	107.9	C12—C13—C14	113.84 (18)
C5—C6—C7	112.33 (18)	C12—C13—H13A	108.8
C5—C6—H6A	109.1	C14—C13—H13A	108.8
C7—C6—H6A	109.1	C12—C13—H13B	108.8
C5—C6—H6B	109.1	C14—C13—H13B	108.8
C7—C6—H6B	109.1	H13A—C13—H13B	107.7
H6A—C6—H6B	107.9	O4—C14—O3	124.47 (19)
O2—C7—O1	124.89 (19)	O4—C14—C13	117.05 (19)
O2—C7—C6	117.22 (19)	O3—C14—C13	118.48 (18)
O1—C7—C6	117.88 (18)	H11W—O1W—H12W	110 (2)
C11—N4—C8	119.92 (17)	H21W—O2W—H22W	104 (2)
C2—N2—C1—N3	178.36 (19)	C9—N5—C8—N6	−179.88 (19)
C2—N2—C1—N1	−2.2 (3)	C9—N5—C8—N4	0.0 (3)
C4—N1—C1—N3	−175.13 (19)	C11—N4—C8—N6	178.78 (19)
C5—N1—C1—N3	4.3 (3)	C12—N4—C8—N6	−0.8 (3)
C4—N1—C1—N2	5.4 (3)	C11—N4—C8—N5	−1.1 (3)
C5—N1—C1—N2	−175.12 (18)	C12—N4—C8—N5	179.27 (18)
C1—N2—C2—C3	−1.6 (3)	C8—N5—C9—C10	1.5 (3)
N2—C2—C3—C4	2.1 (3)	N5—C9—C10—C11	−1.8 (3)
C2—C3—C4—N1	1.2 (3)	C9—C10—C11—N4	0.6 (3)
C1—N1—C4—C3	−4.9 (3)	C8—N4—C11—C10	0.8 (3)
C5—N1—C4—C3	175.6 (2)	C12—N4—C11—C10	−179.63 (19)
C4—N1—C5—C6	90.1 (2)	C11—N4—C12—C13	−101.4 (2)
C1—N1—C5—C6	−89.4 (2)	C8—N4—C12—C13	78.2 (2)
N1—C5—C6—C7	179.52 (17)	N4—C12—C13—C14	−175.40 (17)
C5—C6—C7—O2	−173.50 (18)	C12—C13—C14—O4	168.71 (18)
C5—C6—C7—O1	6.4 (3)	C12—C13—C14—O3	−11.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H31N···O4i	0.85 (3)	2.05 (3)	2.882 (3)	170 (2)
N3—H32N···O3	0.91 (2)	1.99 (2)	2.888 (2)	166 (2)
N6—H61N···O2ii	0.85 (3)	2.12 (3)	2.960 (3)	170 (2)
N6—H62N···O1	0.90 (2)	1.88 (2)	2.766 (2)	169 (2)
O1W—H11W···O3	0.89 (3)	1.93 (3)	2.794 (2)	165 (3)
O1W—H12W···O2iii	0.84 (3)	2.04 (3)	2.867 (2)	170 (3)
O2W—H21W···O1	0.90 (3)	2.00 (3)	2.863 (2)	159 (2)
O2W—H22W···O4iv	0.86 (3)	2.10 (3)	2.923 (2)	159 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H31N⋯O4i	0.85 (3)	2.05 (3)	2.882 (3)	170 (2)
N3—H32N⋯O3	0.91 (2)	1.99 (2)	2.888 (2)	166 (2)
N6—H61N⋯O2ii	0.85 (3)	2.12 (3)	2.960 (3)	170 (2)
N6—H62N⋯O1	0.90 (2)	1.88 (2)	2.766 (2)	169 (2)
O1W—H11W⋯O3	0.89 (3)	1.93 (3)	2.794 (2)	165 (3)
O1W—H12W⋯O2iii	0.84 (3)	2.04 (3)	2.867 (2)	170 (3)
O2W—H21W⋯O1	0.90 (3)	2.00 (3)	2.863 (2)	159 (2)
O2W—H22W⋯O4iv	0.86 (3)	2.10 (3)	2.923 (2)	159 (3)

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