2-Phenyl­imidazolium chloride monohydrate

Xia, D.-C.; Yao, J.-H.

doi:10.1107/S1600536810006136

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o673

doi:10.1107/S1600536810006136

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2-Phenylimidazolium chloride monohydrate

Dao-Cheng Xia ^a ^* and Ji-Huan Yao ^a

^aYuncheng University, College of Chemistry, Yuncheng 044000, People's Republic of China
^*Correspondence e-mail: xiadaocheng1976@yahoo.com.cn

(Received 6 February 2010; accepted 16 February 2010; online 20 February 2010)

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.

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_r = 198.65
Triclinic, $[P \overline 1]$
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 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) 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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.074
S = 0.81
2030 reflections
126 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) x, y-1, z; (ii) -x, -y+1, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006136/om2320sup1.cif

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

checkCIF report

Comment top

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 top

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 top

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).

Computing details top

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 top

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 top

Crystal data top

C₉H₉N₂⁺·Cl⁻·H₂O	Z = 2
M_r = 198.65	F(000) = 208
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0394P)²] where P = (F_o² + 2F_c²)/3
2030 reflections	(Δ/σ)_max < 0.001
126 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₉H₉N₂⁺·Cl⁻·H₂O	γ = 109.337 (13)°
M_r = 198.65	V = 499.65 (15) Å³
Triclinic, P1	Z = 2
a = 7.2751 (10) Å	Mo Kα radiation
b = 8.8816 (13) Å	µ = 0.34 mm⁻¹
c = 9.3228 (10) Å	T = 293 K
α = 105.486 (11)°	0.31 × 0.24 × 0.22 mm
β = 106.516 (11)°

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	2030 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	1198 reflections with I > 2σ(I)
T_min = 0.52, T_max = 0.78	R_int = 0.025
3460 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	Δρ_max = 0.16 e Å⁻³
2030 reflections	Δρ_min = −0.25 e Å⁻³
126 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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)

Geometric parameters (Å, º) top

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) top

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) x, y−1, z; (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₉H₉N₂⁺·Cl⁻·H₂O
M_r	198.65
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.2751 (10), 8.8816 (13), 9.3228 (10)
α, β, γ (°)	105.486 (11), 106.516 (11), 109.337 (13)
V (Å³)	499.65 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.31 × 0.24 × 0.22

Data collection
Diffractometer	Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.52, 0.78
No. of measured, independent and observed [I > 2σ(I)] reflections	3460, 2030, 1198
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.074, 0.81
No. of reflections	2030
No. of parameters	126
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.25

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1W	0.86	1.96	2.774 (2)	157.1
N2—H2···Cl1ⁱ	0.86	2.28	3.1371 (14)	172.0
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) x, y−1, z; (ii) −x, −y+1, −z.

Acknowledgements

We thank Yuncheng University for support.

References

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