2-Phenyl­imidazole dihydrogen phosphate phospho­ric acid

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

doi:10.1107/S1600536810004927

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o609

doi:10.1107/S1600536810004927

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2-Phenylimidazole dihydrogen phosphate phosphoric acid

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 5 February 2010; accepted 8 February 2010; online 13 February 2010)

The crystal structure of the title compound, C₉H₉N₂⁺·H₂PO₄⁻·H₃PO₄, is stabilized by N—H⋯O and O—H⋯O hydrogen-bonding interactions, resulting in a two-dimensional network.

Related literature

For related structures, see: Liu et al. (2008 ); Yang et al. (2008 ); Xia et al. (2009 ).

Experimental

Crystal data

C₉H₉N₂⁺·H₂PO₄⁻·H₃PO₄
M_r = 340.16
Monoclinic, P 2₁ /c
a = 17.1875 (12) Å
b = 4.7220 (3) Å
c = 17.7585 (14) Å
β = 99.767 (7)°
V = 1420.38 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.20 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 = 0.61, T_max = 0.84
5555 measured reflections
2893 independent reflections
1549 reflections with I > 2.0 σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.080
S = 0.87
2893 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O2ⁱ	0.82	1.91	2.563 (2)	136
O3—H3A⋯O2ⁱⁱ	0.82	1.76	2.546 (2)	159
O8—H8A⋯O6ⁱⁱⁱ	0.82	2.01	2.553 (2)	123
N2—H2⋯O6ⁱⁱⁱ	0.86	2.05	2.859 (3)	157
N1—H1B⋯O4	0.86	2.02	2.871 (3)	169
O7—H7⋯O4^iv	0.82	1.76	2.536 (3)	158
O1—H1⋯O3ⁱⁱⁱ	0.82	2.19	2.625 (2)	113
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+2; (iii) x, y+1, z; (iv) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536810004927/pv2259sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004927/pv2259Isup2.hkl

checkCIF report

Comment top

2-Phenylimidazole is a good candidate for building supramolecular architectures (Liu et al., 2008; Yang et al., 2008). Continuing our research in this important field (Xia et al., 2009), we now report the preparation and crystal structure of the title compound, (I).

The asymmetric unit of the title compound contains one 2-phenylimidazole cation, one dihydrogen phosphate anion and one phosphoric acid molecule (Fig. 1). The structure is stabilized by the O—H···O and N—H···O H–bonding interactions (Table 1); a rather weak interaction of the type C—H···O is also present in the structure.

Related literature top

For related structures, see: Liu et al. (2008); Yang et al. (2008); Xia et al. (2009).

Experimental top

A mixture of 2-phenylimidazole (0.5 mmol), phosphoric acid (1 mmol) and H₂O (30 mmol) was mixed. After two weeks, colorless crystals of (I) were yielded at room temperature (18% 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 (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

2-Phenylimidazole dihydrogen phosphate phosphoric acid top

Crystal data top

C₉H₉N₂⁺·H₂PO₄⁻·H₃PO₄	F(000) = 704
M_r = 340.16	D_x = 1.591 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2893 reflections
a = 17.1875 (12) Å	θ = 2.3–26.4°
b = 4.7220 (3) Å	µ = 0.35 mm⁻¹
c = 17.7585 (14) Å	T = 293 K
β = 99.767 (7)°	Block, colorless
V = 1420.38 (17) Å³	0.25 × 0.22 × 0.20 mm
Z = 4

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	2893 independent reflections
Radiation source: fine-focus sealed tube	1549 reflections with I > 2.0 σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 10.0 pixels mm^-1	θ_max = 26.4°, θ_min = 2.3°
ω scan	h = −21→21
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −5→4
T_min = 0.61, T_max = 0.84	l = −13→22
5555 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 0.87	w = 1/[σ²(F_o²) + (0.0302P)²] where P = (F_o² + 2F_c²)/3
2893 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₉H₉N₂⁺·H₂PO₄⁻·H₃PO₄	V = 1420.38 (17) Å³
M_r = 340.16	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.1875 (12) Å	µ = 0.35 mm⁻¹
b = 4.7220 (3) Å	T = 293 K
c = 17.7585 (14) Å	0.25 × 0.22 × 0.20 mm
β = 99.767 (7)°

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	2893 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	1549 reflections with I > 2.0 σ(I)
T_min = 0.61, T_max = 0.84	R_int = 0.038
5555 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 0.87	Δρ_max = 0.27 e Å⁻³
2893 reflections	Δρ_min = −0.37 e Å⁻³
190 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
P1	0.21882 (4)	−0.03732 (14)	0.43687 (4)	0.0302 (2)
P2	0.42236 (4)	0.04439 (15)	0.89806 (4)	0.0299 (2)
O4	0.35030 (10)	−0.0447 (4)	0.84416 (10)	0.0393 (5)
O5	0.28575 (10)	0.0703 (4)	0.50061 (9)	0.0381 (5)
H5A	0.3047	0.2162	0.4864	0.057*
O3	0.48015 (11)	−0.2115 (3)	0.91299 (11)	0.0381 (5)
H3A	0.5199	−0.1635	0.9425	0.057*
O6	0.18630 (11)	−0.3002 (3)	0.46455 (11)	0.0388 (5)
O2	0.40773 (10)	0.1605 (4)	0.97411 (10)	0.0380 (5)
O7	0.25178 (11)	−0.0717 (4)	0.36199 (10)	0.0428 (5)
H7	0.2877	−0.1882	0.3682	0.064*
O1	0.46827 (11)	0.2710 (4)	0.85825 (11)	0.0399 (5)
H1	0.4399	0.4091	0.8466	0.060*
O8	0.15458 (10)	0.1928 (4)	0.41974 (11)	0.0405 (5)
H8A	0.1738	0.3365	0.4045	0.061*
N2	0.26383 (14)	0.5520 (5)	0.61475 (12)	0.0382 (6)
H2	0.2309	0.6152	0.5765	0.046*
N1	0.31292 (13)	0.3278 (5)	0.71534 (12)	0.0395 (6)
H1B	0.3176	0.2181	0.7545	0.047*
C5	0.16191 (18)	0.0460 (7)	0.72484 (19)	0.0548 (9)
H5	0.2037	0.0178	0.7649	0.066*
C8	0.37239 (17)	0.4892 (6)	0.69554 (17)	0.0443 (8)
H8	0.4242	0.4991	0.7212	0.053*
C6	0.17162 (16)	0.2248 (6)	0.66598 (16)	0.0361 (7)
C3	0.0300 (2)	−0.0510 (8)	0.6673 (2)	0.0657 (10)
H3	−0.0174	−0.1454	0.6676	0.079*
C9	0.34158 (17)	0.6299 (6)	0.63224 (17)	0.0429 (8)
H9	0.3679	0.7565	0.6052	0.051*
C2	0.03804 (19)	0.1260 (9)	0.6094 (2)	0.0719 (11)
H2A	−0.0043	0.1531	0.5699	0.086*
C7	0.24664 (16)	0.3649 (6)	0.66528 (15)	0.0332 (7)
C1	0.10825 (19)	0.2679 (8)	0.60773 (18)	0.0604 (10)
H1A	0.1128	0.3911	0.5678	0.072*
C4	0.0923 (2)	−0.0905 (8)	0.7256 (2)	0.0691 (10)
H4	0.0870	−0.2109	0.7658	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0327 (4)	0.0264 (4)	0.0305 (4)	−0.0009 (3)	0.0027 (3)	−0.0005 (3)
P2	0.0291 (4)	0.0297 (4)	0.0301 (4)	0.0019 (3)	0.0027 (3)	0.0022 (3)
O4	0.0320 (10)	0.0512 (12)	0.0313 (11)	−0.0061 (9)	−0.0042 (9)	0.0072 (9)
O5	0.0402 (11)	0.0425 (11)	0.0293 (11)	−0.0111 (9)	−0.0012 (9)	0.0036 (9)
O3	0.0348 (11)	0.0290 (10)	0.0457 (13)	0.0045 (8)	−0.0063 (9)	−0.0022 (9)
O6	0.0451 (12)	0.0271 (10)	0.0430 (13)	−0.0067 (9)	0.0036 (10)	−0.0010 (9)
O2	0.0331 (11)	0.0520 (12)	0.0283 (11)	0.0102 (9)	0.0033 (9)	−0.0007 (9)
O7	0.0525 (13)	0.0445 (12)	0.0315 (12)	0.0114 (10)	0.0077 (9)	0.0030 (9)
O1	0.0448 (12)	0.0311 (10)	0.0461 (13)	0.0029 (9)	0.0136 (10)	0.0066 (9)
O8	0.0350 (12)	0.0289 (10)	0.0547 (15)	0.0002 (9)	−0.0011 (10)	−0.0008 (9)
N2	0.0431 (15)	0.0443 (14)	0.0263 (14)	0.0063 (12)	0.0031 (11)	0.0070 (12)
N1	0.0407 (16)	0.0522 (15)	0.0246 (14)	−0.0007 (12)	0.0023 (12)	0.0090 (11)
C5	0.0418 (19)	0.065 (2)	0.054 (2)	−0.0073 (17)	−0.0042 (16)	0.0145 (18)
C8	0.0353 (17)	0.061 (2)	0.0354 (18)	−0.0041 (15)	0.0028 (14)	0.0083 (16)
C6	0.0346 (18)	0.0438 (17)	0.0296 (19)	0.0066 (14)	0.0049 (14)	−0.0059 (14)
C3	0.042 (2)	0.079 (3)	0.077 (3)	−0.0129 (19)	0.013 (2)	−0.012 (2)
C9	0.0433 (19)	0.0520 (19)	0.0337 (19)	−0.0065 (16)	0.0073 (15)	0.0051 (15)
C2	0.041 (2)	0.117 (3)	0.051 (3)	−0.001 (2)	−0.0093 (18)	−0.004 (2)
C7	0.0368 (17)	0.0394 (16)	0.0234 (16)	0.0082 (14)	0.0052 (14)	−0.0019 (13)
C1	0.041 (2)	0.097 (3)	0.039 (2)	−0.0023 (18)	−0.0026 (17)	0.0111 (18)
C4	0.051 (2)	0.081 (3)	0.074 (3)	−0.0155 (19)	0.007 (2)	0.018 (2)

Geometric parameters (Å, º) top

P1—O6	1.4790 (18)	N1—C8	1.368 (3)
P1—O7	1.5400 (19)	N1—H1B	0.8600
P1—O8	1.5421 (18)	C5—C4	1.361 (4)
P1—O5	1.5559 (17)	C5—C6	1.376 (4)
P2—O4	1.4916 (18)	C5—H5	0.9300
P2—O2	1.5175 (19)	C8—C9	1.335 (4)
P2—O3	1.5579 (18)	C8—H8	0.9300
P2—O1	1.568 (2)	C6—C1	1.384 (4)
O5—H5A	0.8200	C6—C7	1.451 (4)
O3—H3A	0.8200	C3—C2	1.350 (5)
O7—H7	0.8200	C3—C4	1.370 (4)
O1—H1	0.8200	C3—H3	0.9300
O8—H8A	0.8200	C9—H9	0.9300
N2—C7	1.328 (3)	C2—C1	1.385 (5)
N2—C9	1.370 (3)	C2—H2A	0.9300
N2—H2	0.8600	C1—H1A	0.9300
N1—C7	1.332 (3)	C4—H4	0.9300

O6—P1—O7	114.43 (11)	C6—C5—H5	119.4
O6—P1—O8	111.01 (11)	C9—C8—N1	106.7 (3)
O7—P1—O8	105.07 (11)	C9—C8—H8	126.7
O6—P1—O5	107.86 (10)	N1—C8—H8	126.7
O7—P1—O5	109.12 (10)	C5—C6—C1	118.5 (3)
O8—P1—O5	109.25 (10)	C5—C6—C7	120.6 (3)
O4—P2—O2	115.35 (11)	C1—C6—C7	120.9 (3)
O4—P2—O3	109.06 (11)	C2—C3—C4	119.5 (3)
O2—P2—O3	109.01 (10)	C2—C3—H3	120.3
O4—P2—O1	109.26 (11)	C4—C3—H3	120.3
O2—P2—O1	109.08 (11)	C8—C9—N2	106.8 (3)
O3—P2—O1	104.53 (11)	C8—C9—H9	126.6
P1—O5—H5A	109.5	N2—C9—H9	126.6
P2—O3—H3A	109.5	C3—C2—C1	121.2 (3)
P1—O7—H7	109.5	C3—C2—H2A	119.4
P2—O1—H1	109.5	C1—C2—H2A	119.4
P1—O8—H8A	109.5	N2—C7—N1	106.0 (2)
C7—N2—C9	110.2 (2)	N2—C7—C6	127.5 (2)
C7—N2—H2	124.9	N1—C7—C6	126.5 (3)
C9—N2—H2	124.9	C6—C1—C2	119.4 (3)
C7—N1—C8	110.3 (2)	C6—C1—H1A	120.3
C7—N1—H1B	124.9	C2—C1—H1A	120.3
C8—N1—H1B	124.9	C5—C4—C3	120.3 (3)
C4—C5—C6	121.2 (3)	C5—C4—H4	119.9
C4—C5—H5	119.4	C3—C4—H4	119.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2ⁱ	0.82	1.91	2.563 (2)	136
O3—H3A···O2ⁱⁱ	0.82	1.76	2.546 (2)	159
O8—H8A···O6ⁱⁱⁱ	0.82	2.01	2.553 (2)	123
N2—H2···O6ⁱⁱⁱ	0.86	2.05	2.859 (3)	157
N1—H1B···O4	0.86	2.02	2.871 (3)	169
O7—H7···O4^iv	0.82	1.76	2.536 (3)	158
O1—H1···O3ⁱⁱⁱ	0.82	2.19	2.625 (2)	113
C9—H9···O5ⁱⁱⁱ	0.93	2.60	3.154 (3)	119

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y, −z+2; (iii) x, y+1, z; (iv) x, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₉H₉N₂⁺·H₂PO₄⁻·H₃PO₄
M_r	340.16
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	17.1875 (12), 4.7220 (3), 17.7585 (14)
β (°)	99.767 (7)
V (Å³)	1420.38 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.25 × 0.22 × 0.20

Data collection
Diffractometer	Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.61, 0.84
No. of measured, independent and observed [I > 2.0 σ(I)] reflections	5555, 2893, 1549
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.080, 0.87
No. of reflections	2893
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.37

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
O5—H5A···O2ⁱ	0.82	1.91	2.563 (2)	136
O3—H3A···O2ⁱⁱ	0.82	1.76	2.546 (2)	159
O8—H8A···O6ⁱⁱⁱ	0.82	2.01	2.553 (2)	123
N2—H2···O6ⁱⁱⁱ	0.86	2.05	2.859 (3)	157
N1—H1B···O4	0.86	2.02	2.871 (3)	169
O7—H7···O4^iv	0.82	1.76	2.536 (3)	158
O1—H1···O3ⁱⁱⁱ	0.82	2.19	2.625 (2)	113

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y, −z+2; (iii) x, y+1, z; (iv) x, −y−1/2, z−1/2.

Acknowledgements

We thank Yuncheng University for support.

References

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