2-Phenyl-imidazole dihydrogen phosphate phospho-ric acid.

The crystal structure of the title compound, C(9)H(9)N(2) (+)·H(2)PO(4) (-)·H(3)PO(4), is stabilized by N-H⋯O and O-H⋯O hydrogen-bonding inter-actions, 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 = 340.16

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.080

S = 0.87

2893 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.37 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004927/pv2259sup1.cif

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

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

C9H9N2+·H2PO4−·H3PO4	F(000) = 704
Mr = 340.16	Dx = 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

Oxford Diffraction Gemini R Ultra diffractometer	2893 independent reflections
Radiation source: fine-focus sealed tube	1549 reflections with I > 2.0 σ(I)
graphite	Rint = 0.038
Detector resolution: 10.0 pixels mm-1	θmax = 26.4°, θmin = 2.3°
ω scan	h = −21→21
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −5→4
Tmin = 0.61, Tmax = 0.84	l = −13→22
5555 measured reflections

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(Fo2) + (0.0302P)2] where P = (Fo2 + 2Fc2)/3
2893 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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···O4iv	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

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⋯O4iv	0.82	1.76	2.536 (3)	158
O1—H1⋯O3iii	0.82	2.19	2.625 (2)	113

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .