6-Nitro­benzimidazolium dihydrogen phosphate 6-nitro­benzimidazole solvate dihydrate

Shao, Z.-D.; Jiang, X.; Lan, S.-M.; Di, W.-J.; Liang, Y.-X.

doi:10.1107/S1600536810023603

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1757-o1758

doi:10.1107/S1600536810023603

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6-Nitrobenzimidazolium dihydrogen phosphate 6-nitrobenzimidazole solvate dihydrate

Zhi-Dong Shao,^a Xiao Jiang,^a Shao-Min Lan,^a Wen-Jing Di ^a and Yun-Xiao Liang ^a ^*

^aState Key Lab. Base of Novel Functional Materials and Preparation Science, Faculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang, 315211, People's Republic of China
^*Correspondence e-mail: liangyunxiao@nbu.edu.cn

(Received 29 May 2010; accepted 18 June 2010; online 23 June 2010)

In the crystal structure of the title compound, C₇H₆N₃O₂⁺·H₂PO₄⁻·C₇H₅N₃O₂·2H₂O, the components are connected through O—H⋯O, N—H⋯O and O—H⋯N hydrogen-bonding interactions, forming a sheet-like structure parallel to (101). Adjacent sheets are further linked together by strong O—H⋯O hydrogen-bonds involving the dihydrogenphosphate groups. π–π stacking interactions between neighbouring aromatic constituents [centroid–centroid distance 3.653 (3) Å] help to consolidate the crystal packing.

Related literature

For the preparation of inorganic metal phosphates, see: Benard et al. (1996 ); Jensen et al. (2000 ). For template synthesis of phosphates, see: Sameski et al. (1993 ); Lii et al. (1998 ). For phosphates with organic cations, see: Dakhlaoui et al. (2007 ).

Experimental

Crystal data

C₇H₆N₃O₂⁺·H₂PO₄⁻·C₇H₅N₃O₂·2H₂O
M_r = 460.31
Triclinic, $[P \overline 1]$
a = 9.4683 (19) Å
b = 9.990 (2) Å
c = 11.407 (2) Å
α = 90.73 (3)°
β = 107.10 (3)°
γ = 111.66 (3)°
V = 949.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.37 × 0.32 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.924, T_max = 0.975
9332 measured reflections
4286 independent reflections
2827 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.141
S = 1.14
4286 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected bond lengths (Å)

P1—O8	1.500 (2)
P1—O7	1.504 (2)
P1—O5	1.5591 (19)
P1—O6	1.562 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O7ⁱ	0.86	1.74	2.600 (2)	179
N2—H2A⋯O9	0.86	1.92	2.752 (2)	164
O6—H6A⋯N4ⁱⁱ	1.03	1.66	2.665 (2)	165
O5—H5A⋯O8ⁱⁱⁱ	0.91	1.62	2.531 (2)	174
N5—H5B⋯O7	0.86	1.91	2.773 (2)	176
O9—H9A⋯O4^iv	0.91	2.43	3.161 (2)	137
O9—H9B⋯O10^v	0.85	1.92	2.754 (2)	165
O10—H10A⋯O8	0.91	1.85	2.740 (2)	169
O10—H10B⋯O9ⁱⁱⁱ	0.84	2.16	2.917 (2)	149
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+2, -z+1; (iv) -x+1, -y+2, -z; (v) x, y, z-1.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ) and DIAMOND (Brandenburg, 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023603/wm2359sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023603/wm2359Isup2.hkl

checkCIF report

Comment top

Phosphates are of great interest because of their rich crystal chemistry and practical applications. Up to now, numerous inorganic metal phosphates have been reported (e.g. Benard et al., 1996; Jensen et al., 2000). Furthermore, various of these phosphates were synthesized by structure-orienting templates molecules, most ferquently amines (Sameski et al., 1993; Lii et al., 1998). Compared with these inorganic phosphates, the synthesis of non-metal phosphates was less well explored in the past decades (Dakhlaoui et al., 2007). Herein, we describe the synthesis and crystal structure of the title compound (I), a new non-metal phosphate with formula (C₇H₆N₃O₂)[H₂PO₄]^.(C₇H₅N₃O₂)^.2(H₂O)

As shown in Fig.1, the structure of (I) consists of one (C₇H₆N₃O₂)⁺ cation, one [H₂PO₄]^- anion, one (C₇H₅N₃O₂) solvent molecule and two H₂O molecules, viz. one imidazole molecule is protonated, one imidazole molecule acts as an unprotonated solvent and a dihydrogenphosphate group is present. The O—P—O angles are in the range 105.62 (11)—115.73 (13) °. The P—O bond lengths to the terminal O atoms are 1.500 (2) and 1.504 (2) Å while the P—OH bond lengths are considerably longer with 1.5591 (19) and 1.562 (2) Å.

As is well known, hydrogen bonding interactions play an important role in the formation and stability of low-dimensional structures. In the present structure, the [(C₇H₆N₃O₂)]⁺ cations, [H₂PO₄]^- anions, (C₇H₅N₃O₂) and H₂O molecules are linked together through hydrogen bonds: N1—H1A···O7, N5—H5B···O7; N2—H2A···O9, O6—H6A···N4, O9—H4A···O4, O9—H9B···O10, O10—H10B···O3 (Fig. 2), forming a two-dimensional sheetlike structure parallel to (101). Adjacent sheets are further linked together by strong H-bonding interactions [O5—H5A···O8, O10—H10A···O8, O10—H10B···O9]. π—π stacking interactions between neighboring 6-nitrobenzimidazole molecules with an interplanar distance of 3.653 (3) Å help to consolidate a three-dimensional supramolecular network structure (Fig. 3).

Related literature top

For the preparation of inorganic metal phosphates, see: Benard et al. (1996); Jensen et al. (2000). For template synthesis of phosphates, see: Sameski et al. (1993); Lii et al. (1998). For phosphates with organic cations, see: Dakhlaoui et al. (2007).

Experimental top

The title compound was obtained by the reaction of phosphoric acid, 6-nitrobenzimidazole and methanol/distilled water under room temperature. Typically, a mixture of phosphoric acid (0.2 ml), analytically pure 6-nitrobenzimidazole (0.164 g) and methanol/distilled water (10 ml/10 ml) was stirred at room temperature before it was filtered. The final filtrate was allowed to evaporate slowly at room temperature for 7 days to obtain yellow crystals.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: Crystal Structure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The layer structure of (C₇H₆N₃O₂)[H₂PO₄]^.(C₇H₅N₃O₂)^.2(H₂O). Hydrogen bonds are indicated by dashed lines.
	Fig. 3. A packing diagram for the title compound, viewed along the a axis. Dashed lines indicate hydrogen bonds.

6-Nitrobenzimidazolium dihydrogen phosphate 6-nitrobenzimidazole solvate dihydrate top

Crystal data top

C₇H₆N₃O₂⁺·H₂PO₄⁻·C₇H₅N₃O₂·2H₂O	Z = 2
M_r = 460.31	F(000) = 476
Triclinic, P1	D_x = 1.610 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4683 (19) Å	Cell parameters from 6404 reflections
b = 9.990 (2) Å	θ = 3.1–27.5°
c = 11.407 (2) Å	µ = 0.22 mm⁻¹
α = 90.73 (3)°	T = 293 K
β = 107.10 (3)°	Platelet, yellow
γ = 111.66 (3)°	0.37 × 0.32 × 0.12 mm
V = 949.4 (3) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	4286 independent reflections
Radiation source: fine-focus sealed tube	2827 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
T_min = 0.924, T_max = 0.975	k = −12→12
9332 measured reflections	l = −14→14

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0532P)² + 0.7024P] where P = (F_o² + 2F_c²)/3
4286 reflections	(Δ/σ)_max = 0.005
280 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₇H₆N₃O₂⁺·H₂PO₄⁻·C₇H₅N₃O₂·2H₂O	γ = 111.66 (3)°
M_r = 460.31	V = 949.4 (3) Å³
Triclinic, P1	Z = 2
a = 9.4683 (19) Å	Mo Kα radiation
b = 9.990 (2) Å	µ = 0.22 mm⁻¹
c = 11.407 (2) Å	T = 293 K
α = 90.73 (3)°	0.37 × 0.32 × 0.12 mm
β = 107.10 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4286 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2827 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.975	R_int = 0.021
9332 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.14	Δρ_max = 0.43 e Å⁻³
4286 reflections	Δρ_min = −0.47 e Å⁻³
280 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
P1	0.46015 (8)	0.77962 (7)	0.52850 (6)	0.03448 (19)
O1	1.0279 (3)	0.6110 (3)	0.1175 (3)	0.0759 (8)
N1	0.4441 (3)	0.4733 (2)	0.2701 (2)	0.0392 (5)
H1A	0.4368	0.4114	0.3221	0.047*
C1	0.6946 (3)	0.4893 (3)	0.2258 (2)	0.0336 (5)
H1B	0.7181	0.4226	0.2760	0.040*
O2	0.9605 (3)	0.4445 (3)	0.2308 (2)	0.0638 (6)
N2	0.3902 (3)	0.6274 (2)	0.1497 (2)	0.0385 (5)
H2A	0.3417	0.6800	0.1120	0.046*
C2	0.5632 (3)	0.5227 (3)	0.2149 (2)	0.0313 (5)
O3	1.1886 (3)	1.0612 (3)	0.1237 (3)	0.0771 (8)
N3	0.9352 (3)	0.5369 (3)	0.1686 (2)	0.0447 (6)
C3	0.5284 (3)	0.6217 (3)	0.1383 (2)	0.0317 (5)
O4	1.0632 (3)	1.1997 (3)	0.1303 (3)	0.0762 (8)
N4	1.0431 (3)	0.7285 (2)	0.4511 (2)	0.0379 (5)
C4	0.6251 (3)	0.6929 (3)	0.0684 (2)	0.0376 (6)
H4B	0.6011	0.7583	0.0168	0.045*
O5	0.4699 (3)	0.8359 (2)	0.40310 (18)	0.0489 (5)
H5A	0.4918	0.9324	0.4014	0.050*
N5	0.8298 (3)	0.7543 (2)	0.47608 (19)	0.0375 (5)
H5B	0.7499	0.7403	0.5024	0.045*
C5	0.7570 (3)	0.6616 (3)	0.0796 (2)	0.0376 (6)
H5C	0.8259	0.7070	0.0355	0.045*
O6	0.2931 (2)	0.6510 (2)	0.4983 (2)	0.0471 (5)
H6A	0.1868	0.6647	0.4826	0.050*
N6	1.0976 (3)	1.0955 (3)	0.1613 (2)	0.0492 (6)
C6	0.7888 (3)	0.5623 (3)	0.1566 (2)	0.0347 (6)
O7	0.5822 (2)	0.7132 (2)	0.57244 (19)	0.0456 (5)
C7	0.3444 (3)	0.5381 (3)	0.2287 (3)	0.0425 (6)
H7B	0.2539	0.5234	0.2518	0.051*
O8	0.4731 (3)	0.8988 (2)	0.61749 (16)	0.0435 (5)
C8	1.0885 (3)	0.9142 (3)	0.3032 (2)	0.0367 (6)
H8B	1.1769	0.9045	0.2902	0.044*
O9	0.2853 (3)	0.8166 (3)	0.0119 (2)	0.0625 (6)
H9A	0.2025	0.8421	0.0112	0.050*
H9B	0.3401	0.8590	−0.0339	0.050*
C9	1.0114 (3)	0.8331 (3)	0.3813 (2)	0.0320 (5)
O10	0.4652 (3)	0.9058 (3)	0.8556 (2)	0.0754 (8)
H10A	0.4652	0.8914	0.7771	0.050*
H10B	0.5564	0.9646	0.9008	0.050*
C10	0.8767 (3)	0.8494 (3)	0.3970 (2)	0.0322 (5)
C11	0.8168 (3)	0.9477 (3)	0.3391 (2)	0.0389 (6)
H11A	0.7279	0.9578	0.3508	0.047*
C12	0.8942 (3)	1.0293 (3)	0.2638 (2)	0.0401 (6)
H12A	0.8592	1.0976	0.2244	0.048*
C13	1.0254 (3)	1.0093 (3)	0.2469 (2)	0.0364 (6)
C14	0.9324 (3)	0.6863 (3)	0.5052 (2)	0.0387 (6)
H14A	0.9253	0.6161	0.5585	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0389 (4)	0.0324 (4)	0.0420 (4)	0.0175 (3)	0.0220 (3)	0.0148 (3)
O1	0.0584 (15)	0.097 (2)	0.104 (2)	0.0408 (15)	0.0564 (15)	0.0469 (16)
N1	0.0364 (12)	0.0418 (13)	0.0442 (13)	0.0156 (10)	0.0187 (10)	0.0156 (10)
C1	0.0338 (13)	0.0333 (13)	0.0338 (13)	0.0131 (11)	0.0109 (10)	0.0113 (10)
O2	0.0587 (14)	0.0820 (17)	0.0750 (16)	0.0482 (14)	0.0283 (12)	0.0319 (13)
N2	0.0416 (13)	0.0427 (13)	0.0403 (12)	0.0253 (11)	0.0146 (10)	0.0109 (10)
C2	0.0294 (12)	0.0323 (13)	0.0327 (13)	0.0109 (10)	0.0120 (10)	0.0063 (10)
O3	0.0843 (18)	0.103 (2)	0.0893 (18)	0.0559 (17)	0.0655 (16)	0.0499 (16)
N3	0.0375 (13)	0.0537 (15)	0.0484 (14)	0.0204 (12)	0.0182 (11)	0.0078 (11)
C3	0.0347 (13)	0.0311 (13)	0.0282 (12)	0.0131 (11)	0.0084 (10)	0.0037 (9)
O4	0.0911 (19)	0.0713 (16)	0.101 (2)	0.0464 (15)	0.0594 (16)	0.0566 (15)
N4	0.0334 (12)	0.0393 (12)	0.0444 (13)	0.0156 (10)	0.0151 (10)	0.0105 (10)
C4	0.0433 (15)	0.0337 (13)	0.0330 (13)	0.0130 (12)	0.0107 (11)	0.0087 (10)
O5	0.0798 (15)	0.0367 (10)	0.0441 (11)	0.0264 (11)	0.0341 (11)	0.0164 (8)
N5	0.0325 (12)	0.0453 (13)	0.0373 (12)	0.0135 (10)	0.0172 (9)	0.0084 (9)
C5	0.0366 (14)	0.0419 (15)	0.0325 (13)	0.0109 (12)	0.0144 (11)	0.0086 (11)
O6	0.0365 (11)	0.0321 (10)	0.0764 (14)	0.0126 (8)	0.0240 (10)	0.0171 (9)
N6	0.0469 (14)	0.0591 (16)	0.0500 (15)	0.0219 (13)	0.0252 (12)	0.0194 (12)
C6	0.0289 (13)	0.0423 (14)	0.0322 (13)	0.0149 (11)	0.0078 (10)	0.0036 (10)
O7	0.0405 (11)	0.0490 (11)	0.0649 (13)	0.0249 (9)	0.0316 (10)	0.0280 (10)
C7	0.0383 (15)	0.0491 (16)	0.0470 (16)	0.0212 (13)	0.0182 (12)	0.0106 (12)
O8	0.0659 (13)	0.0377 (10)	0.0380 (10)	0.0233 (10)	0.0281 (9)	0.0151 (8)
C8	0.0297 (13)	0.0420 (15)	0.0407 (14)	0.0125 (11)	0.0166 (11)	0.0042 (11)
O9	0.0635 (14)	0.0811 (16)	0.0725 (15)	0.0465 (13)	0.0389 (12)	0.0432 (12)
C9	0.0291 (12)	0.0320 (13)	0.0331 (13)	0.0088 (10)	0.0116 (10)	0.0031 (10)
O10	0.0840 (19)	0.100 (2)	0.0467 (13)	0.0308 (16)	0.0344 (13)	0.0136 (13)
C10	0.0298 (13)	0.0349 (13)	0.0319 (13)	0.0097 (11)	0.0133 (10)	0.0055 (10)
C11	0.0332 (14)	0.0465 (15)	0.0410 (15)	0.0189 (12)	0.0133 (11)	0.0054 (11)
C12	0.0376 (14)	0.0437 (15)	0.0426 (15)	0.0183 (12)	0.0148 (12)	0.0108 (11)
C13	0.0357 (14)	0.0355 (14)	0.0360 (14)	0.0090 (11)	0.0150 (11)	0.0075 (10)
C14	0.0367 (14)	0.0356 (14)	0.0417 (15)	0.0111 (12)	0.0132 (11)	0.0093 (11)

Geometric parameters (Å, º) top

P1—O8	1.500 (2)	O5—H5A	0.9100
P1—O7	1.504 (2)	N5—C14	1.348 (4)
P1—O5	1.5591 (19)	N5—C10	1.364 (3)
P1—O6	1.562 (2)	N5—H5B	0.8600
O1—N3	1.221 (3)	C5—C6	1.391 (4)
N1—C7	1.315 (4)	C5—H5C	0.9300
N1—C2	1.388 (3)	O6—H6A	1.0287
N1—H1A	0.8600	N6—C13	1.463 (3)
C1—C2	1.376 (3)	C7—H7B	0.9300
C1—C6	1.378 (3)	C8—C13	1.371 (4)
C1—H1B	0.9300	C8—C9	1.396 (3)
O2—N3	1.221 (3)	C8—H8B	0.9300
N2—C7	1.328 (3)	O9—H9A	0.9074
N2—C3	1.374 (3)	O9—H9B	0.8512
N2—H2A	0.8600	C9—C10	1.405 (3)
C2—C3	1.393 (3)	O10—H10A	0.9048
O3—N6	1.215 (3)	O10—H10B	0.8438
N3—C6	1.467 (3)	C10—C11	1.389 (4)
C3—C4	1.394 (4)	C11—C12	1.373 (4)
O4—N6	1.228 (3)	C11—H11A	0.9300
N4—C14	1.310 (3)	C12—C13	1.395 (4)
N4—C9	1.388 (3)	C12—H12A	0.9300
C4—C5	1.367 (4)	C14—H14A	0.9300
C4—H4B	0.9300

O8—P1—O7	115.73 (13)	C6—C5—H5C	119.8
O8—P1—O5	109.95 (10)	P1—O6—H6A	123.8
O7—P1—O5	108.51 (11)	O3—N6—O4	122.7 (3)
O8—P1—O6	110.30 (12)	O3—N6—C13	118.9 (3)
O7—P1—O6	105.62 (11)	O4—N6—C13	118.4 (2)
O5—P1—O6	106.23 (13)	C1—C6—C5	124.3 (2)
C7—N1—C2	107.7 (2)	C1—C6—N3	117.6 (2)
C7—N1—H1A	126.2	C5—C6—N3	118.0 (2)
C2—N1—H1A	126.2	N1—C7—N2	110.9 (2)
C2—C1—C6	114.8 (2)	N1—C7—H7B	124.5
C2—C1—H1B	122.6	N2—C7—H7B	124.5
C6—C1—H1B	122.6	C13—C8—C9	115.7 (2)
C7—N2—C3	108.4 (2)	C13—C8—H8B	122.2
C7—N2—H2A	125.8	C9—C8—H8B	122.2
C3—N2—H2A	125.8	H9A—O9—H9B	116.1
C1—C2—N1	131.2 (2)	N4—C9—C8	130.5 (2)
C1—C2—C3	122.0 (2)	N4—C9—C10	109.0 (2)
N1—C2—C3	106.8 (2)	C8—C9—C10	120.4 (2)
O1—N3—O2	122.8 (3)	H10A—O10—H10B	110.3
O1—N3—C6	118.4 (2)	N5—C10—C11	132.1 (2)
O2—N3—C6	118.8 (2)	N5—C10—C9	105.6 (2)
N2—C3—C2	106.2 (2)	C11—C10—C9	122.3 (2)
N2—C3—C4	131.9 (2)	C12—C11—C10	117.3 (2)
C2—C3—C4	121.9 (2)	C12—C11—H11A	121.4
C14—N4—C9	104.8 (2)	C10—C11—H11A	121.4
C5—C4—C3	116.5 (2)	C11—C12—C13	119.7 (3)
C5—C4—H4B	121.8	C11—C12—H12A	120.1
C3—C4—H4B	121.8	C13—C12—H12A	120.1
P1—O5—H5A	115.9	C8—C13—C12	124.6 (2)
C14—N5—C10	107.1 (2)	C8—C13—N6	118.7 (2)
C14—N5—H5B	126.5	C12—C13—N6	116.7 (2)
C10—N5—H5B	126.5	N4—C14—N5	113.5 (2)
C4—C5—C6	120.4 (2)	N4—C14—H14A	123.3
C4—C5—H5C	119.8	N5—C14—H14A	123.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O7ⁱ	0.86	1.74	2.600 (2)	179
N2—H2A···O9	0.86	1.92	2.752 (2)	164
O6—H6A···N4ⁱⁱ	1.03	1.66	2.665 (2)	165
O5—H5A···O8ⁱⁱⁱ	0.91	1.62	2.531 (2)	174
N5—H5B···O7	0.86	1.91	2.773 (2)	176
O9—H9A···O3ⁱⁱ	0.91	2.59	3.269 (2)	132
O9—H9A···O4^iv	0.91	2.43	3.161 (2)	137
O9—H9B···O10^v	0.85	1.92	2.754 (2)	165
O10—H10A···O8	0.91	1.85	2.740 (2)	169
O10—H10B···O9ⁱⁱⁱ	0.84	2.16	2.917 (2)	149
O10—H10B···O3^vi	0.84	2.61	3.106 (2)	119

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

Experimental details

Crystal data
Chemical formula	C₇H₆N₃O₂⁺·H₂PO₄⁻·C₇H₅N₃O₂·2H₂O
M_r	460.31
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.4683 (19), 9.990 (2), 11.407 (2)
α, β, γ (°)	90.73 (3), 107.10 (3), 111.66 (3)
V (Å³)	949.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.37 × 0.32 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.924, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	9332, 4286, 2827
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.141, 1.14
No. of reflections	4286
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.47

Computer programs: RAPID-AUTO (Rigaku, 1998), Crystal Structure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2008).

Selected bond lengths (Å) top

P1—O8	1.500 (2)	P1—O5	1.5591 (19)
P1—O7	1.504 (2)	P1—O6	1.562 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O7ⁱ	0.86	1.74	2.600 (2)	179
N2—H2A···O9	0.86	1.92	2.752 (2)	164
O6—H6A···N4ⁱⁱ	1.03	1.66	2.665 (2)	165
O5—H5A···O8ⁱⁱⁱ	0.91	1.62	2.531 (2)	174
N5—H5B···O7	0.86	1.91	2.773 (2)	176
O9—H9A···O4^iv	0.91	2.43	3.161 (2)	137
O9—H9B···O10^v	0.85	1.92	2.754 (2)	165
O10—H10A···O8	0.91	1.85	2.740 (2)	169
O10—H10B···O9ⁱⁱⁱ	0.84	2.16	2.917 (2)	149

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

Acknowledgements

This work was supported by the Ningbo Natural Science Foundation (grant Nos. 2007 A610022 and 2009 A610052) and the K. C. Wong Magna Fund in Ningbo University.

References

Benard, P., Brandel, V., Dacheux, N., Jaulmes, S., Launay, S., Lindecker, C., Genet, M. & Quarton, M. (1996). Chem. Mater. 8, 181–188. CrossRef CAS Web of Science Google Scholar
Brandenburg, K. (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Dakhlaoui, A., Gmigui, K. & Smiri, L. S. (2007). Acta Cryst. E63, o537–o539. Web of Science CSD CrossRef IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Jensen, T. R., Hazell, R. G., Vosegaard, T. & Jakobsen, H. J. (2000). Inorg. Chem. 39, 2026–2032. Web of Science CrossRef PubMed CAS Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL–5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Lii, K.-H., Huang, Y.-F., Huang, C.-Y., Lin, H.-M., Jiang, Y.-C., Liao, F.-L. & Wang, S.-L. (1998). Chem. Mater. 10, 2599–2609. Web of Science CrossRef CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sameski, J. E., Brzezinski, L. J., Anderson, B., Didiuk, M., Manchanda, R., Crabtree, R. H., BrudVig, G. W. & Schulte, G. K. (1993). Inorg. Chem. 32, 3265–3269. Google Scholar
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Volume 66| Part 7| July 2010| Pages o1757-o1758

doi:10.1107/S1600536810023603

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6-Nitro­benzimidazolium di­hydrogen phosphate 6-nitro­benzimidazole solvate dihydrate

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Experimental

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organic compounds

6-Nitrobenzimidazolium dihydrogen phosphate 6-nitrobenzimidazole solvate dihydrate