2-Phenyl­imidazolium chloride monohydrate

In the title hydrated molecular salt, C₉H₉N₂⁺·Cl⁻·H₂O, 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 inter­actions are present in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.074
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

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Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          6
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         15

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The 2-phenylimidazolium nitrate structure has been reported as a hemihydrate (Zhang et al., 2007) and as a hydrate (Xia et al., 2009). Here we report the synthesis and structure of the chloride hydrate, namely, C₉H₁₁ClN₂O.

The asymmetric unit of the title compound contains one 2-phenylimidazolium cation, one chloride anion and one water molecule (Fig. 1). There are O—H···Cl, N—H···O and N—H···Cl H-bonding interactions in the structure (Table I).

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).

S2. Experimental

A mixture of 2-phenylimidazole (0.5 mmol), hydrochloric acid (0.5 mmol) and H₂O (30 mmol) was mixed. After two weeks, colorless crystals were obtained at room temperature (22% yield).

S3. Refinement

All H atoms on C and N atoms were positioned geometrically (N—H = 0.86 Å and C—H = 0.93 Å) and refined as riding, with U_iso(H)=1.2U_eq(carrier). The water H-atom was located in a difference Fourier map, and was refined freely.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD (Oxford Diffraction, 2006); 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 (Sheldrick, 2008).

Figures

Fig. 1. The structure of the title compound showing the atomic numbering scheme and displacement ellipsoids at the 30% probability level.

2-Phenylimidazolium chloride monohydrate

Crystal data

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) Å^3

Data collection

Oxford Diffraction Gemini R Ultra diffractometer	2030 independent reflections
Radiation source: fine-focus sealed tube	1198 reflections with I > 2σ(I)
Graphite monochromator	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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	w = 1/[σ^2(Fo^2) + (0.0394P)^2] where P = (Fo^2 + 2Fc^2)/3
2030 reflections	(Δ/σ)max < 0.001
126 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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···Cl1^i	0.86	2.28	3.1371 (14)	172
O1W—HW11···Cl1	0.86 (3)	2.33 (3)	3.177 (2)	174 (2)
O1W—HW12···Cl1^ii	0.88 (3)	2.32 (3)	3.190 (2)	176 (2)

Symmetry codes: (i) x, y−1, z; (ii) −x, −y+1, −z.