6-Nitro-benzimidazolium dihydrogen phosphate 6-nitro-benzimidazole solvate dihydrate.

In the crystal structure of the title compound, C(7)H(6)N(3)O(2) (+)·H(2)PO(4) (-)·C(7)H(5)N(3)O(2)·2H(2)O, the components are connected through O-H⋯O, N-H⋯O and O-H⋯N hydrogen-bonding inter-actions, 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 inter-actions 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 = 460.31

Triclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.141

S = 1.14

4286 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.47 e Å−3

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.

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

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

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

C7H6N3O2+·H2PO4−·C7H5N3O2·2H2O	Z = 2
Mr = 460.31	F(000) = 476
Triclinic, P1	Dx = 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

Rigaku R-AXIS RAPID diffractometer	4286 independent reflections
Radiation source: fine-focus sealed tube	2827 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
Tmin = 0.924, Tmax = 0.975	k = −12→12
9332 measured reflections	l = −14→14

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(Fo2) + (0.0532P)2 + 0.7024P] where P = (Fo2 + 2Fc2)/3
4286 reflections	(Δ/σ)max = 0.005
280 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.47 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
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*

	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)

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

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···O4iv	0.91	2.43	3.161 (2)	137
O9—H9B···O10v	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···O3vi	0.84	2.61	3.106 (2)	119

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⋯O4iv	0.91	2.43	3.161 (2)	137
O9—H9B⋯O10v	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) ; (ii) ; (iii) ; (iv) ; (v) .