1-Carboxy-methyl-2-ethyl-4-methyl-1H-imidazol-3-ium chloride monohydrate.

In the title compound, C(8)H(13)N(2)O(2) (+)·Cl(-)·H(2)O, the methyl C atom of the ethyl group is slightly out of the imidazole plane, with an N-C(ring)-C-C torsion angle of -15.1 (2)°. In the crystal structure, there are strong inter-molecular hydrogen-bonding inter-actions between the solvent water mol-ecule, the free chloride anion and the organic cation, resulting in a two-dimensional supra-molecular network in the ab plane.

Related literature

The title compound is a vital intermediate in the synthesis of bisphosphonic acid, i.e. n class="Chemical">2-(2-ethyl-4-methyl-1H-imidazol-1-yl)-1-hydroxyethane-1,1-diyldiphosphonic acid; for a general background on bis­phospho­nates, see: Dawson (2003 ▶); Vasireddy et al. (2003 ▶). For related structures, see: Gao et al. (2004 ▶); Barczynski et al. (2008 ▶). For the synthesis, see: Zederenko et al. (1994 ▶).

Experimental

Crystal data

C8H13N2O2 +·Cl−·n class="Chemical">H2O

M = 222.67

Monoclinic,

a = 11.077 (2) Å

b = 8.4542 (18) Å

c = 11.938 (3) Å

β = 90.265 (3)°

V = 1117.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 93 K

0.40 × 0.40 × 0.35 mm

Data collection

Rigaku SPIDER diffractometer

Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 2004 ▶) T min = 0.880, T max = 0.894

8869 measured reflections

2532 independent reflections

2203 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.099

S = 1.00

2532 reflections

145 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.20 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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 global, I. DOI: 10.1107/S1600536809013403/fj2205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013403/fj2205Isup2.hkl

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

C8H13N2O2+·Cl−·H2O	F(000) = 472
Mr = 222.67	Dx = 1.323 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3544 reflections
a = 11.077 (2) Å	θ = 3.0–27.5°
b = 8.4542 (18) Å	µ = 0.33 mm−1
c = 11.938 (3) Å	T = 93 K
β = 90.265 (3)°	Block, colorless
V = 1117.9 (4) Å3	0.40 × 0.40 × 0.35 mm
Z = 4

Rigaku SPIDER diffractometer	2532 independent reflections
Radiation source: Rotating Anode	2203 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 2004)	h = −13→14
Tmin = 0.880, Tmax = 0.894	k = −10→10
8869 measured reflections	l = −15→14

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0582P)2 + 0.06P] where P = (Fo2 + 2Fc2)/3
2532 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.29 e Å−3
1 restraint	Δρmin = −0.20 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
Cl1	0.19761 (3)	0.57092 (4)	0.31835 (3)	0.02509 (14)
O1	0.88525 (10)	0.95264 (13)	0.14174 (10)	0.0295 (3)
O2	0.79630 (9)	0.72040 (13)	0.17923 (9)	0.0273 (3)
O3	0.40590 (10)	0.32662 (16)	0.33959 (12)	0.0382 (3)
N1	0.42391 (11)	0.70595 (14)	0.18900 (10)	0.0184 (3)
N2	0.57147 (10)	0.84373 (14)	0.12622 (10)	0.0184 (3)
C1	0.42085 (12)	0.68984 (18)	0.07348 (12)	0.0210 (3)
C2	0.51409 (12)	0.77535 (17)	0.03442 (12)	0.0211 (3)
H2	0.5366	0.7869	−0.0418	0.025*
C3	0.51465 (12)	0.79974 (16)	0.21927 (12)	0.0178 (3)
C4	0.32597 (14)	0.5958 (2)	0.01537 (14)	0.0292 (4)
H4A	0.3426	0.5934	−0.0652	0.035*
H4B	0.2469	0.6445	0.0281	0.035*
H4C	0.3258	0.4877	0.0449	0.035*
C5	0.54916 (13)	0.84647 (19)	0.33464 (12)	0.0234 (3)
H5A	0.5677	0.9610	0.3355	0.028*
H5B	0.6236	0.7891	0.3562	0.028*
C6	0.45261 (15)	0.8131 (2)	0.42068 (13)	0.0304 (4)
H6A	0.3789	0.8710	0.4008	0.037*
H6B	0.4809	0.8473	0.4947	0.037*
H6C	0.4355	0.6994	0.4222	0.037*
C7	0.67760 (12)	0.94450 (17)	0.12097 (12)	0.0202 (3)
H7A	0.6672	1.0345	0.1731	0.024*
H7B	0.6849	0.9879	0.0443	0.024*
C8	0.79233 (12)	0.85727 (18)	0.15091 (12)	0.0205 (3)
H1N	0.3693 (15)	0.667 (2)	0.2348 (14)	0.027 (4)*
H1O	0.961 (2)	0.900 (3)	0.1558 (18)	0.060 (7)*
H3A	0.344 (2)	0.397 (3)	0.336 (2)	0.077 (8)*
H3B	0.385 (2)	0.243 (3)	0.289 (2)	0.067 (7)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0190 (2)	0.0276 (2)	0.0287 (2)	−0.00309 (14)	0.00545 (15)	−0.00028 (14)
O1	0.0168 (5)	0.0245 (6)	0.0472 (7)	−0.0020 (5)	0.0009 (5)	0.0008 (5)
O2	0.0199 (5)	0.0236 (6)	0.0384 (6)	0.0035 (4)	0.0019 (5)	0.0087 (5)
O3	0.0206 (6)	0.0333 (7)	0.0605 (9)	0.0012 (5)	−0.0053 (6)	−0.0059 (6)
N1	0.0141 (6)	0.0215 (6)	0.0196 (6)	−0.0007 (5)	0.0018 (5)	−0.0005 (5)
N2	0.0139 (6)	0.0212 (6)	0.0202 (6)	0.0015 (5)	0.0002 (5)	0.0007 (5)
C1	0.0162 (7)	0.0250 (8)	0.0220 (7)	0.0033 (6)	−0.0002 (6)	−0.0028 (6)
C2	0.0178 (7)	0.0276 (8)	0.0178 (7)	0.0040 (6)	0.0004 (5)	−0.0008 (6)
C3	0.0139 (6)	0.0179 (7)	0.0217 (7)	0.0029 (5)	0.0018 (5)	−0.0005 (5)
C4	0.0202 (8)	0.0392 (10)	0.0281 (8)	−0.0016 (7)	−0.0013 (6)	−0.0088 (7)
C5	0.0236 (8)	0.0269 (8)	0.0197 (7)	−0.0040 (6)	−0.0004 (6)	−0.0027 (6)
C6	0.0303 (9)	0.0381 (10)	0.0229 (8)	−0.0054 (7)	0.0031 (7)	−0.0040 (7)
C7	0.0165 (7)	0.0195 (7)	0.0247 (7)	−0.0007 (6)	0.0021 (6)	0.0018 (5)
C8	0.0173 (7)	0.0232 (8)	0.0211 (7)	−0.0001 (6)	0.0021 (6)	−0.0003 (6)

O1—C8	1.3125 (18)	C3—C5	1.481 (2)
O1—H1O	0.96 (2)	C4—H4A	0.9800
O2—C8	1.2063 (18)	C4—H4B	0.9800
O3—H3A	0.91 (2)	C4—H4C	0.9800
O3—H3B	0.96 (2)	C5—C6	1.513 (2)
N1—C3	1.3290 (18)	C5—H5A	0.9900
N1—C1	1.3860 (18)	C5—H5B	0.9900
N1—H1N	0.881 (17)	C6—H6A	0.9800
N2—C3	1.3322 (18)	C6—H6B	0.9800
N2—C2	1.3903 (18)	C6—H6C	0.9800
N2—C7	1.4534 (18)	C7—C8	1.5109 (19)
C1—C2	1.346 (2)	C7—H7A	0.9900
C1—C4	1.487 (2)	C7—H7B	0.9900
C2—H2	0.9500
C8—O1—H1O	112.3 (13)	H4B—C4—H4C	109.5
H3A—O3—H3B	106.1 (16)	C3—C5—C6	113.66 (12)
C3—N1—C1	110.13 (12)	C3—C5—H5A	108.8
C3—N1—H1N	125.1 (11)	C6—C5—H5A	108.8
C1—N1—H1N	124.5 (11)	C3—C5—H5B	108.8
C3—N2—C2	108.97 (12)	C6—C5—H5B	108.8
C3—N2—C7	125.80 (12)	H5A—C5—H5B	107.7
C2—N2—C7	125.22 (12)	C5—C6—H6A	109.5
C2—C1—N1	106.06 (12)	C5—C6—H6B	109.5
C2—C1—C4	131.87 (14)	H6A—C6—H6B	109.5
N1—C1—C4	122.06 (13)	C5—C6—H6C	109.5
C1—C2—N2	107.40 (13)	H6A—C6—H6C	109.5
C1—C2—H2	126.3	H6B—C6—H6C	109.5
N2—C2—H2	126.3	N2—C7—C8	112.54 (12)
N1—C3—N2	107.43 (12)	N2—C7—H7A	109.1
N1—C3—C5	127.13 (13)	C8—C7—H7A	109.1
N2—C3—C5	125.44 (13)	N2—C7—H7B	109.1
C1—C4—H4A	109.5	C8—C7—H7B	109.1
C1—C4—H4B	109.5	H7A—C7—H7B	107.8
H4A—C4—H4B	109.5	O2—C8—O1	125.81 (14)
C1—C4—H4C	109.5	O2—C8—C7	124.34 (13)
H4A—C4—H4C	109.5	O1—C8—C7	109.85 (13)
C3—N1—C1—C2	0.88 (16)	C7—N2—C3—N1	−178.83 (12)
C3—N1—C1—C4	−177.84 (13)	C2—N2—C3—C5	179.31 (13)
N1—C1—C2—N2	−0.76 (16)	C7—N2—C3—C5	0.3 (2)
C4—C1—C2—N2	177.78 (15)	N1—C3—C5—C6	−15.1 (2)
C3—N2—C2—C1	0.40 (16)	N2—C3—C5—C6	165.88 (14)
C7—N2—C2—C1	179.39 (13)	C3—N2—C7—C8	77.86 (17)
C1—N1—C3—N2	−0.63 (16)	C2—N2—C7—C8	−100.96 (15)
C1—N1—C3—C5	−179.78 (14)	N2—C7—C8—O2	−2.0 (2)
C2—N2—C3—N1	0.14 (15)	N2—C7—C8—O1	178.25 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl1	0.881 (17)	2.300 (18)	3.1635 (14)	166.6 (15)
O3—H3A···Cl1	0.91 (2)	2.20 (2)	3.1062 (14)	177 (2)
O1—H1O···O3i	0.96 (2)	1.60 (2)	2.5557 (16)	170 (2)
O3—H3B···Cl1ii	0.96 (2)	2.14 (2)	3.0860 (14)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl1	0.881 (17)	2.300 (18)	3.1635 (14)	166.6 (15)
O3—H3A⋯Cl1	0.91 (2)	2.20 (2)	3.1062 (14)	177 (2)
O1—H1O⋯O3i	0.96 (2)	1.60 (2)	2.5557 (16)	170 (2)
O3—H3B⋯Cl1ii	0.96 (2)	2.14 (2)	3.0860 (14)	168.2 (19)

Symmetry codes: (i) ; (ii) .