2-Phenyl-imidazolium chloride monohydrate.

In the title hydrated molecular salt, C(9)H(9)N(2) (+)·Cl(-)·H(2)O, the dihedral angle between the five- and six-membered rings in the cation is 18.00 (2)°. O-H⋯Cl, N-H⋯O and N-H⋯Cl hrdrogen-bonding inter-actions are present in the crystal structure.

Related literature

For related 2-phenyl­imidazolium nitrate structures, see: Zhang et al. (2007 ▶); Xia et al. (2009 ▶). For a phosphate salt of phenyl­imadazole, see: Xia & Yao (2010 ▶) and for a silver complex, see: Han et al. (2010 ▶).

Experimental

Crystal data

C9H9N2 +·Cl−·H2O

M = 198.65

Triclinic,

a = 7.2751 (10) Å

b = 8.8816 (13) Å

c = 9.3228 (10) Å

α = 105.486 (11)°

β = 106.516 (11)°

γ = 109.337 (13)°

V = 499.65 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.31 × 0.24 × 0.22 mm

Data collection

Oxford Diffraction Gemini R Ultra diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.52, T max = 0.78

3460 measured reflections

2030 independent reflections

1198 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.074

S = 0.81

2030 reflections

126 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); 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/S1600536810006136/om2320sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006136/om2320Isup2.hkl

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

C9H9N2+·Cl−·H2O	Z = 2
Mr = 198.65	F(000) = 208
Triclinic, P1	Dx = 1.320 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2751 (10) Å	Cell parameters from 2030 reflections
b = 8.8816 (13) Å	θ = 2.5–26.4°
c = 9.3228 (10) Å	µ = 0.34 mm−1
α = 105.486 (11)°	T = 293 K
β = 106.516 (11)°	Block, colorless
γ = 109.337 (13)°	0.31 × 0.24 × 0.22 mm
V = 499.65 (15) Å3

Oxford Diffraction Gemini R Ultra diffractometer	2030 independent reflections
Radiation source: fine-focus sealed tube	1198 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 10.0 pixels mm-1	θmax = 26.4°, θmin = 2.5°
ω scan	h = −6→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −10→11
Tmin = 0.52, Tmax = 0.78	l = −11→9
3460 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	w = 1/[σ2(Fo2) + (0.0394P)2] where P = (Fo2 + 2Fc2)/3
2030 reflections	(Δ/σ)max < 0.001
126 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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 > 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
C1	0.4640 (3)	0.2399 (2)	0.3466 (2)	0.0617 (5)
H1A	0.5140	0.2530	0.4549	0.074*
C2	0.4744 (3)	0.3668 (2)	0.2929 (2)	0.0653 (6)
H2A	0.5322	0.4849	0.3570	0.078*
C3	0.3188 (3)	0.1197 (2)	0.0774 (2)	0.0437 (4)
C4	0.2201 (3)	−0.0061 (2)	−0.0909 (2)	0.0441 (4)
C5	0.1124 (3)	−0.1827 (2)	−0.1299 (2)	0.0548 (5)
H5	0.1007	−0.2215	−0.0482	0.066*
C6	0.0231 (3)	−0.3006 (2)	−0.2889 (2)	0.0665 (6)
H6	−0.0509	−0.4186	−0.3146	0.080*
C7	0.0428 (3)	−0.2445 (3)	−0.4101 (3)	0.0693 (6)
H7	−0.0167	−0.3247	−0.5174	0.083*
C8	0.1500 (3)	−0.0708 (3)	−0.3728 (2)	0.0661 (6)
H8	0.1634	−0.0336	−0.4551	0.079*
C9	0.2382 (3)	0.0496 (2)	−0.2145 (2)	0.0550 (5)
H9	0.3095	0.1676	−0.1903	0.066*
N1	0.3844 (2)	0.29054 (16)	0.12684 (18)	0.0543 (4)
H1	0.3719	0.3448	0.0635	0.065*
N2	0.3658 (2)	0.08756 (17)	0.21156 (17)	0.0504 (4)
H2	0.3385	−0.0138	0.2129	0.060*
O1W	0.2454 (3)	0.4594 (2)	−0.0598 (3)	0.0680 (4)
HW11	0.249 (4)	0.538 (3)	0.019 (3)	0.114 (11)*
HW12	0.107 (5)	0.407 (3)	−0.117 (3)	0.122 (11)*
Cl1	0.26211 (8)	0.73220 (5)	0.25005 (5)	0.0634 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0669 (14)	0.0637 (12)	0.0518 (12)	0.0312 (10)	0.0177 (10)	0.0234 (10)
C2	0.0746 (14)	0.0527 (11)	0.0572 (14)	0.0266 (10)	0.0189 (11)	0.0164 (9)
C3	0.0437 (10)	0.0496 (10)	0.0537 (11)	0.0267 (8)	0.0245 (8)	0.0305 (8)
C4	0.0444 (10)	0.0503 (10)	0.0551 (11)	0.0291 (8)	0.0245 (9)	0.0311 (8)
C5	0.0648 (13)	0.0558 (11)	0.0580 (12)	0.0308 (10)	0.0284 (10)	0.0340 (9)
C6	0.0788 (15)	0.0552 (11)	0.0645 (14)	0.0289 (10)	0.0271 (11)	0.0255 (10)
C7	0.0787 (15)	0.0748 (14)	0.0579 (13)	0.0407 (12)	0.0277 (11)	0.0229 (10)
C8	0.0818 (15)	0.0869 (14)	0.0602 (14)	0.0500 (12)	0.0389 (11)	0.0459 (11)
C9	0.0628 (12)	0.0587 (11)	0.0663 (13)	0.0335 (10)	0.0350 (10)	0.0397 (10)
N1	0.0650 (10)	0.0474 (9)	0.0635 (11)	0.0286 (7)	0.0295 (8)	0.0324 (7)
N2	0.0566 (10)	0.0501 (8)	0.0560 (10)	0.0293 (7)	0.0218 (8)	0.0316 (7)
O1W	0.0656 (12)	0.0655 (9)	0.0919 (12)	0.0366 (8)	0.0345 (9)	0.0460 (9)
Cl1	0.0715 (3)	0.0529 (3)	0.0548 (3)	0.0174 (2)	0.0143 (2)	0.0311 (2)

C1—C2	1.339 (2)	C6—C7	1.375 (3)
C1—N2	1.366 (2)	C6—H6	0.9300
C1—H1A	0.9300	C7—C8	1.368 (3)
C2—N1	1.362 (2)	C7—H7	0.9300
C2—H2A	0.9300	C8—C9	1.378 (3)
C3—N1	1.3282 (19)	C8—H8	0.9300
C3—N2	1.332 (2)	C9—H9	0.9300
C3—C4	1.455 (2)	N1—H1	0.8600
C4—C5	1.388 (2)	N2—H2	0.8600
C4—C9	1.392 (2)	O1W—HW11	0.86 (3)
C5—C6	1.374 (3)	O1W—HW12	0.88 (3)
C5—H5	0.9300
C2—C1—N2	106.67 (17)	C7—C6—H6	119.9
C2—C1—H1A	126.7	C8—C7—C6	120.01 (19)
N2—C1—H1A	126.7	C8—C7—H7	120.0
C1—C2—N1	107.20 (16)	C6—C7—H7	120.0
C1—C2—H2A	126.4	C7—C8—C9	120.68 (17)
N1—C2—H2A	126.4	C7—C8—H8	119.7
N1—C3—N2	106.63 (14)	C9—C8—H8	119.7
N1—C3—C4	126.29 (15)	C8—C9—C4	119.67 (16)
N2—C3—C4	127.06 (15)	C8—C9—H9	120.2
C5—C4—C9	119.14 (16)	C4—C9—H9	120.2
C5—C4—C3	120.82 (15)	C3—N1—C2	109.75 (14)
C9—C4—C3	120.01 (15)	C3—N1—H1	125.1
C6—C5—C4	120.30 (16)	C2—N1—H1	125.1
C6—C5—H5	119.8	C3—N2—C1	109.74 (14)
C4—C5—H5	119.8	C3—N2—H2	125.1
C5—C6—C7	120.18 (18)	C1—N2—H2	125.1
C5—C6—H6	119.9	HW11—O1W—HW12	97 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1W	0.86	1.96	2.774 (2)	157
N2—H2···Cl1i	0.86	2.28	3.1371 (14)	172
O1W—HW11···Cl1	0.86 (3)	2.33 (3)	3.177 (2)	174 (2)
O1W—HW12···Cl1ii	0.88 (3)	2.32 (3)	3.190 (2)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1W	0.86	1.96	2.774 (2)	157
N2—H2⋯Cl1i	0.86	2.28	3.1371 (14)	172
O1W—HW11⋯Cl1	0.86 (3)	2.33 (3)	3.177 (2)	174 (2)
O1W—HW12⋯Cl1ii	0.88 (3)	2.32 (3)	3.190 (2)	176 (2)

Symmetry codes: (i) ; (ii) .