2-Phenyl-imidazolium nitrate monohydrate.

In the title hydrated mol-ecular salt, C(9)H(9)N(2) (+)·NO(3) (-)·H(2)O, the dihedral angle between the aromatic rings in the cation is 11.09 (8)°. In the crystal, the components are linked into chains propagating in [101] by N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For related structures containing 2-phenyl­imidazole, see: Liu et al. (2008 ▶); Yang et al. (2008 ▶).

Experimental

Crystal data

C9H9N2 +·NO3 −·H2O

M = 225.21

Monoclinic,

a = 8.026 (4) Å

b = 14.951 (7) Å

c = 8.895 (5) Å

β = 101.096 (5)°

V = 1047.4 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.33 × 0.28 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.56, T max = 0.81

4388 measured reflections

2407 independent reflections

1430 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.104

S = 0.88

2407 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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/S1600536809050703/hb5245sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050703/hb5245Isup2.hkl

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

C9H9N2+·NO3−·H2O	F(000) = 472
Mr = 225.21	Dx = 1.428 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2407 reflections
a = 8.026 (4) Å	θ = 3.0–29.2°
b = 14.951 (7) Å	µ = 0.11 mm−1
c = 8.895 (5) Å	T = 293 K
β = 101.096 (5)°	Block, colourless
V = 1047.4 (9) Å3	0.33 × 0.28 × 0.22 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2407 independent reflections
Radiation source: fine-focus sealed tube	1430 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 29.2°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.56, Tmax = 0.81	k = −19→20
4388 measured reflections	l = −7→12

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	w = 1/[σ2(Fo2) + (0.0625P)2] where P = (Fo2 + 2Fc2)/3
2407 reflections	(Δ/σ)max < 0.001
153 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.21 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
C1	0.41911 (19)	−0.16151 (10)	1.11954 (17)	0.0528 (4)
H1	0.4944	−0.1975	1.1858	0.063*
C2	0.31545 (19)	−0.18758 (10)	0.99079 (18)	0.0532 (4)
H2A	0.3044	−0.2452	0.9508	0.064*
C3	0.27630 (15)	−0.04284 (9)	1.01806 (14)	0.0382 (3)
C4	0.21609 (15)	0.04875 (9)	0.99206 (14)	0.0375 (3)
C5	0.11719 (17)	0.07305 (9)	0.85184 (15)	0.0475 (4)
H5	0.0869	0.0302	0.7756	0.057*
C6	0.0641 (2)	0.15982 (10)	0.82541 (19)	0.0591 (4)
H6	−0.0019	0.1753	0.7313	0.071*
C7	0.1073 (2)	0.22399 (10)	0.9361 (2)	0.0626 (5)
H7	0.0726	0.2829	0.9169	0.075*
C8	0.2026 (2)	0.20012 (10)	1.0760 (2)	0.0609 (4)
H8	0.2306	0.2432	1.1521	0.073*
C9	0.25738 (17)	0.11317 (9)	1.10495 (17)	0.0502 (4)
H9	0.3218	0.0979	1.1999	0.060*
N1	0.31081 (15)	0.01630 (11)	0.54668 (14)	0.0575 (4)
N2	0.22881 (14)	−0.11327 (7)	0.92928 (13)	0.0452 (3)
H2	0.1546	−0.1123	0.8455	0.054*
N3	0.39323 (14)	−0.07206 (7)	1.13512 (12)	0.0455 (3)
H3	0.4446	−0.0394	1.2093	0.055*
O1	0.39439 (12)	−0.03171 (7)	0.64925 (11)	0.0619 (3)
O2	0.20267 (15)	−0.01926 (11)	0.44597 (13)	0.0921 (5)
O1W	0.03846 (18)	−0.13296 (8)	0.63882 (14)	0.0607 (3)
O3	0.33396 (17)	0.09768 (10)	0.54776 (15)	0.0860 (4)
HW11	−0.049 (3)	−0.1037 (14)	0.606 (2)	0.090 (7)*
HW12	0.104 (2)	−0.1081 (14)	0.584 (2)	0.097 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0531 (9)	0.0454 (9)	0.0587 (10)	0.0079 (7)	0.0078 (7)	0.0124 (7)
C2	0.0587 (9)	0.0372 (8)	0.0638 (10)	0.0043 (7)	0.0121 (7)	0.0023 (7)
C3	0.0371 (7)	0.0404 (7)	0.0367 (7)	−0.0022 (6)	0.0065 (5)	0.0017 (6)
C4	0.0352 (6)	0.0388 (7)	0.0394 (7)	−0.0026 (6)	0.0094 (5)	0.0004 (6)
C5	0.0537 (8)	0.0446 (8)	0.0435 (8)	0.0045 (7)	0.0076 (6)	0.0002 (6)
C6	0.0647 (9)	0.0536 (10)	0.0584 (9)	0.0137 (8)	0.0103 (7)	0.0122 (8)
C7	0.0614 (10)	0.0393 (8)	0.0896 (13)	0.0091 (7)	0.0210 (9)	0.0066 (8)
C8	0.0573 (9)	0.0459 (9)	0.0798 (12)	−0.0053 (8)	0.0140 (8)	−0.0217 (8)
C9	0.0478 (8)	0.0504 (8)	0.0502 (9)	−0.0019 (7)	0.0037 (6)	−0.0079 (7)
N1	0.0460 (7)	0.0799 (11)	0.0466 (8)	0.0057 (7)	0.0090 (6)	0.0068 (7)
N2	0.0488 (7)	0.0375 (6)	0.0461 (7)	−0.0002 (5)	0.0013 (5)	0.0004 (5)
N3	0.0459 (6)	0.0464 (7)	0.0418 (7)	0.0006 (5)	0.0020 (5)	0.0022 (5)
O1	0.0602 (7)	0.0620 (7)	0.0550 (7)	0.0060 (5)	−0.0102 (5)	0.0027 (5)
O2	0.0663 (7)	0.1416 (14)	0.0571 (8)	−0.0208 (8)	−0.0163 (6)	0.0107 (8)
O1W	0.0608 (7)	0.0538 (7)	0.0612 (8)	−0.0042 (6)	−0.0041 (6)	−0.0026 (5)
O3	0.1057 (11)	0.0655 (9)	0.0903 (10)	0.0136 (7)	0.0277 (8)	0.0200 (7)

C1—C2	1.337 (2)	C6—H6	0.9300
C1—N3	1.3646 (19)	C7—C8	1.376 (2)
C1—H1	0.9300	C7—H7	0.9300
C2—N2	1.3678 (18)	C8—C9	1.380 (2)
C2—H2A	0.9300	C8—H8	0.9300
C3—N2	1.3274 (17)	C9—H9	0.9300
C3—N3	1.3340 (17)	N1—O3	1.2305 (19)
C3—C4	1.4556 (19)	N1—O2	1.2406 (17)
C4—C9	1.3849 (19)	N1—O1	1.2498 (16)
C4—C5	1.3917 (19)	N2—H2	0.8600
C5—C6	1.372 (2)	N3—H3	0.8600
C5—H5	0.9300	O1W—HW11	0.83 (2)
C6—C7	1.371 (2)	O1W—HW12	0.87 (2)
C2—C1—N3	106.90 (12)	C6—C7—H7	120.4
C2—C1—H1	126.5	C8—C7—H7	120.4
N3—C1—H1	126.5	C7—C8—C9	120.96 (14)
C1—C2—N2	106.88 (13)	C7—C8—H8	119.5
C1—C2—H2A	126.6	C9—C8—H8	119.5
N2—C2—H2A	126.6	C8—C9—C4	119.77 (14)
N2—C3—N3	106.43 (12)	C8—C9—H9	120.1
N2—C3—C4	127.10 (12)	C4—C9—H9	120.1
N3—C3—C4	126.46 (12)	O3—N1—O2	120.86 (15)
C9—C4—C5	118.94 (13)	O3—N1—O1	120.21 (14)
C9—C4—C3	120.88 (12)	O2—N1—O1	118.92 (17)
C5—C4—C3	120.18 (12)	C3—N2—C2	109.92 (11)
C6—C5—C4	120.35 (13)	C3—N2—H2	125.0
C6—C5—H5	119.8	C2—N2—H2	125.0
C4—C5—H5	119.8	C3—N3—C1	109.86 (12)
C7—C6—C5	120.78 (15)	C3—N3—H3	125.1
C7—C6—H6	119.6	C1—N3—H3	125.1
C5—C6—H6	119.6	HW11—O1W—HW12	98.1 (18)
C6—C7—C8	119.18 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1W	0.86	1.92	2.753 (2)	163
N3—H3···O1i	0.86	1.94	2.7809 (17)	166
O1W—HW11···O2ii	0.83 (2)	2.21 (2)	2.989 (2)	155.3 (19)
O1W—HW12···O2	0.87 (2)	2.07 (2)	2.905 (2)	162.3 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1W	0.86	1.92	2.753 (2)	163
N3—H3⋯O1i	0.86	1.94	2.7809 (17)	166
O1W—HW11⋯O2ii	0.83 (2)	2.21 (2)	2.989 (2)	155.3 (19)
O1W—HW12⋯O2	0.87 (2)	2.07 (2)	2.905 (2)	162.3 (19)

Symmetry codes: (i) ; (ii) .