2-Phenyl­imidazolium nitrate monohydrate

Xia, D.-C.; Li, W.-C.; Han, S.

doi:10.1107/S1600536809050703

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3283

doi:10.1107/S1600536809050703

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2-Phenylimidazolium nitrate monohydrate

Dao-Cheng Xia,^a ^* Wan-Cheng Li ^b and Shuang Han ^a

^aYuncheng University, College of Chemistry, Yuncheng 044000, People's Republic of China, and ^bState Key Laboratory of Integrated Optoelectronics, Jilin University, Changchun 130021, People's Republic of China
^*Correspondence e-mail: xiadaocheng1976@yahoo.com.cn

(Received 21 November 2009; accepted 25 November 2009; online 28 November 2009)

In the title hydrated molecular salt, C₉H₉N₂⁺·NO₃⁻·H₂O, 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_r = 225.21
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.104
S = 0.88
2407 reflections
153 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) -x+1, -y, -z+2; (ii) -x, -y, -z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050703/hb5245sup1.cif

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

checkCIF report

Comment top

2-Phenylimidazole, as an important N-containing ligand with excellent coordinating abilities and fruitful aromatic systems, have been extensively used to build supramolecular architectures (Liu et al., 2008; Yang et al., 2008). We report here the synthesis and structure of the title compound, namely, C₉H₁₁N₃O₄ (I)

There are one 2-phenylimidazole cation, one nitrate anion and one water molecule in the asymmetric unit of the title compound, C₉H₁₁N₃O₄ (Fig. 1). In the crystal, molecules are linked into layer structures by N—H···O and O—H···O H-bonding interactions (Table 1).

Related literature top

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

Experimental top

A mixture of Cu(NO₃)₂^.2.5H₂O (0.5 mmol), 2-phenylimidazole (0.5 mmol), and H₂O (30 mmol) was heated in a sealed vessel at 413 K for 2 days. After the mixture was slowly cooled to room temperature, colorless blocks of (I) were obtained (23% yield).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (I), showing displacement ellipsoids drawn at the 30% probability level.

2-Phenylimidazolium nitrate monohydrate top

Crystal data top

C₉H₉N₂⁺·NO₃⁻·H₂O	F(000) = 472
M_r = 225.21	D_x = 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

Data collection top

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

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)] = 0.040	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(F_o²) + (0.0625P)²] where P = (F_o² + 2F_c²)/3
2407 reflections	(Δ/σ)_max < 0.001
153 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₉H₉N₂⁺·NO₃⁻·H₂O	V = 1047.4 (9) Å³
M_r = 225.21	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.026 (4) Å	µ = 0.11 mm⁻¹
b = 14.951 (7) Å	T = 293 K
c = 8.895 (5) Å	0.33 × 0.28 × 0.22 mm
β = 101.096 (5)°

Data collection top

Bruker SMART APEX CCD diffractometer	2407 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1430 reflections with I > 2σ(I)
T_min = 0.56, T_max = 0.81	R_int = 0.018
4388 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	Δρ_max = 0.15 e Å⁻³
2407 reflections	Δρ_min = −0.21 e Å⁻³
153 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+2; (ii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₉H₉N₂⁺·NO₃⁻·H₂O
M_r	225.21
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.026 (4), 14.951 (7), 8.895 (5)
β (°)	101.096 (5)
V (Å³)	1047.4 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.33 × 0.28 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.56, 0.81
No. of measured, independent and observed [I > 2σ(I)] reflections	4388, 2407, 1430
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.104, 0.88
No. of reflections	2407
No. of parameters	153
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.21

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), 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
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) −x+1, −y, −z+2; (ii) −x, −y, −z+1.

Acknowledgements

We thank Yuncheng University and Jilin University for support.

References

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