2,6-Diethyl-anilinium dihydrogen phosphate-phospho-ric acid (1/1).

In the crystal structure of the title salt, C(10)H(16)N(+)·H(2)PO(4) (-)·H(3)PO(4), the H(2)PO(4) (-) and H(3)PO(4) components are connected into infinite chains extending along the b-axis direction by way of O-H⋯O links. These chains are also linked through O-H⋯O hydrogen bonds thus building up a supra-molecular two-dimensional framework extending parallel to (001). The organic cations cross-link the anionic layers by way of multiple N-H⋯O inter-actions, leading to a cohesive network.

Related literature

For hydrogen bonds, see: Blessing (1986 ▶); Desiraju (1995 ▶). For their biological occurence, see: Richards et al. (1972 ▶); Perutz & Ten Eyck (1972 ▶). For related structures with n class="Chemical">phosphoric acid, see: Belam et al. (2005 ▶); Mighell et al. (1969 ▶); Smith et al. (1955 ▶). For related organic cations, see: Akriche & Rzaigui (2008 ▶); Smirani Sta et al. (2010 ▶).

Experimental

Crystal data

C10H16N+·n class="Chemical">H2O4P−·H3O4P

M = 345.22

Monoclinic,

a = 8.1634 (10) Å

b = 7.707 (2) Å

c = 25.680 (6) Å

β = 102.686 (19)°

V = 1576.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.45 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

5173 measured reflections

2776 independent reflections

2417 reflections with I > 2σ(I)

R int = 0.011

2 standard reflections every 120 min intensity decay: 4%

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.104

S = 1.06

2776 reflections

198 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.47 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and n class="Disease">DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051159/dn2632sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051159/dn2632Isup2.hkl

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

C10H16N+·H2O4P−·H3O4P	F(000) = 728
Mr = 345.22	Dx = 1.455 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.1634 (10) Å	θ = 9–11°
b = 7.707 (2) Å	µ = 0.31 mm−1
c = 25.680 (6) Å	T = 293 K
β = 102.686 (19)°	Prism, colourless
V = 1576.2 (6) Å3	0.45 × 0.30 × 0.20 mm
Z = 4

Enraf–Nonius TurboCAD-4 diffractometer	Rint = 0.011
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.6°
graphite	h = −9→9
non–profiled ω scans	k = −9→0
5173 measured reflections	l = −30→26
2776 independent reflections	2 standard reflections every 120 min
2417 reflections with I > 2σ(I)	intensity decay: 4%

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0631P)2 + 0.6675P] where P = (Fo2 + 2Fc2)/3
2776 reflections	(Δ/σ)max = 0.001
198 parameters	Δρmax = 0.27 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	0.89551 (6)	0.42643 (7)	0.69762 (2)	0.02954 (17)
P2	0.57483 (6)	0.63702 (6)	0.78754 (2)	0.02854 (16)
O1	0.90841 (18)	0.36241 (19)	0.75328 (6)	0.0396 (4)
O2	0.9067 (2)	0.6272 (2)	0.69495 (7)	0.0520 (5)
H2	0.9850	0.6616	0.7184	0.078*
O3	0.72469 (17)	0.39370 (19)	0.65968 (6)	0.0391 (4)
H3	0.6783	0.3113	0.6706	0.059*
O4	1.0255 (2)	0.3435 (3)	0.67058 (7)	0.0600 (5)
H4	1.1176	0.3437	0.6913	0.090*
O5	0.69580 (18)	0.48369 (19)	0.80976 (6)	0.0388 (4)
H5	0.7548	0.4612	0.7886	0.058*
O6	0.49043 (19)	0.59476 (19)	0.72822 (6)	0.0387 (4)
H6	0.4372	0.5041	0.7269	0.058*
O7	0.66900 (17)	0.80396 (18)	0.78532 (7)	0.0400 (4)
O8	0.44861 (18)	0.63937 (18)	0.82220 (6)	0.0379 (4)
N1	0.6019 (2)	0.8023 (2)	0.64703 (7)	0.0376 (4)
H1A	0.5247	0.7406	0.6585	0.056*
H1B	0.5939	0.9133	0.6558	0.056*
H1C	0.7036	0.7626	0.6621	0.056*
C1	0.5743 (3)	0.7867 (3)	0.58854 (9)	0.0389 (5)
C2	0.4324 (3)	0.7015 (3)	0.56111 (10)	0.0469 (6)
C3	0.4120 (4)	0.6914 (3)	0.50585 (11)	0.0575 (7)
H3A	0.3183	0.6356	0.4856	0.069*
C4	0.5292 (4)	0.7631 (4)	0.48074 (10)	0.0613 (7)
H4A	0.5136	0.7546	0.4439	0.074*
C5	0.6679 (4)	0.8466 (3)	0.50942 (10)	0.0555 (7)
H5A	0.7453	0.8938	0.4917	0.067*
C6	0.6953 (3)	0.8624 (3)	0.56494 (9)	0.0452 (6)
C7	0.3079 (4)	0.6215 (4)	0.59107 (12)	0.0626 (7)
H7A	0.3650	0.5291	0.6136	0.075*
H7B	0.2783	0.7095	0.6144	0.075*
C8	0.1485 (4)	0.5490 (5)	0.55760 (15)	0.0829 (10)
H8A	0.0873	0.6398	0.5362	0.124*
H8B	0.0812	0.5013	0.5804	0.124*
H8C	0.1750	0.4594	0.5348	0.124*
C9	0.8439 (4)	0.9572 (4)	0.59828 (11)	0.0589 (7)
H9A	0.8011	1.0495	0.6173	0.071*
H9B	0.9036	0.8768	0.6248	0.071*
C10	0.9693 (4)	1.0357 (5)	0.56996 (13)	0.0706 (8)
H10A	1.0219	0.9453	0.5537	0.106*
H10B	1.0532	1.0977	0.5952	0.106*
H10C	0.9128	1.1143	0.5429	0.106*

	U11	U22	U33	U12	U13	U23
P1	0.0263 (3)	0.0247 (3)	0.0378 (3)	0.00059 (19)	0.0075 (2)	0.0007 (2)
P2	0.0267 (3)	0.0179 (3)	0.0428 (3)	0.00200 (18)	0.0113 (2)	0.0022 (2)
O1	0.0415 (8)	0.0350 (8)	0.0435 (8)	0.0127 (6)	0.0116 (7)	0.0082 (6)
O2	0.0617 (11)	0.0258 (9)	0.0574 (11)	−0.0121 (7)	−0.0108 (8)	0.0056 (7)
O3	0.0319 (8)	0.0319 (8)	0.0508 (9)	−0.0057 (6)	0.0033 (7)	0.0076 (7)
O4	0.0376 (9)	0.0916 (15)	0.0514 (10)	0.0181 (9)	0.0113 (7)	−0.0113 (10)
O5	0.0412 (8)	0.0293 (8)	0.0496 (9)	0.0141 (6)	0.0182 (7)	0.0093 (7)
O6	0.0469 (9)	0.0261 (8)	0.0437 (8)	−0.0069 (6)	0.0111 (7)	0.0043 (6)
O7	0.0295 (7)	0.0216 (7)	0.0689 (10)	−0.0021 (6)	0.0105 (7)	0.0031 (7)
O8	0.0375 (8)	0.0277 (8)	0.0533 (9)	0.0065 (6)	0.0203 (7)	0.0026 (7)
N1	0.0473 (10)	0.0293 (9)	0.0390 (10)	0.0005 (8)	0.0154 (8)	0.0022 (7)
C1	0.0564 (13)	0.0247 (10)	0.0368 (11)	0.0084 (9)	0.0130 (10)	0.0011 (8)
C2	0.0609 (14)	0.0301 (12)	0.0472 (13)	0.0067 (11)	0.0065 (11)	0.0013 (10)
C3	0.0760 (18)	0.0397 (14)	0.0497 (15)	0.0056 (13)	−0.0014 (13)	−0.0045 (11)
C4	0.101 (2)	0.0459 (15)	0.0362 (13)	0.0114 (15)	0.0134 (14)	−0.0023 (11)
C5	0.0851 (19)	0.0433 (14)	0.0443 (14)	0.0056 (13)	0.0279 (13)	0.0005 (11)
C6	0.0645 (15)	0.0335 (12)	0.0421 (12)	0.0054 (10)	0.0215 (11)	0.0010 (10)
C7	0.0640 (17)	0.0617 (18)	0.0573 (16)	−0.0121 (14)	0.0027 (13)	0.0002 (13)
C8	0.074 (2)	0.079 (2)	0.089 (2)	−0.0143 (18)	0.0033 (18)	−0.0070 (19)
C9	0.0748 (18)	0.0567 (16)	0.0522 (15)	−0.0140 (14)	0.0290 (13)	−0.0032 (12)
C10	0.077 (2)	0.077 (2)	0.0653 (18)	−0.0115 (17)	0.0303 (15)	0.0042 (16)

P1—O1	1.4937 (16)	C2—C7	1.532 (4)
P1—O4	1.5296 (16)	C3—C4	1.381 (4)
P1—O3	1.5364 (15)	C3—H3A	0.9300
P1—O2	1.5525 (17)	C4—C5	1.368 (4)
P2—O8	1.5022 (15)	C4—H4A	0.9300
P2—O7	1.5063 (15)	C5—C6	1.399 (3)
P2—O6	1.5622 (16)	C5—H5A	0.9300
P2—O5	1.5652 (14)	C6—C9	1.511 (4)
O2—H2	0.8200	C7—C8	1.501 (4)
O3—H3	0.8200	C7—H7A	0.9700
O4—H4	0.8200	C7—H7B	0.9700
O5—H5	0.8200	C8—H8A	0.9600
O6—H6	0.8200	C8—H8B	0.9600
N1—C1	1.474 (3)	C8—H8C	0.9600
N1—H1A	0.8900	C9—C10	1.507 (4)
N1—H1B	0.8900	C9—H9A	0.9700
N1—H1C	0.8900	C9—H9B	0.9700
C1—C2	1.382 (3)	C10—H10A	0.9600
C1—C6	1.395 (3)	C10—H10B	0.9600
C2—C3	1.394 (4)	C10—H10C	0.9600
O1—P1—O4	112.72 (10)	C5—C4—H4A	119.6
O1—P1—O3	114.58 (9)	C3—C4—H4A	119.6
O4—P1—O3	105.49 (10)	C4—C5—C6	121.2 (3)
O1—P1—O2	112.27 (10)	C4—C5—H5A	119.4
O4—P1—O2	110.04 (12)	C6—C5—H5A	119.4
O3—P1—O2	100.93 (9)	C1—C6—C5	115.9 (2)
O8—P2—O7	115.74 (9)	C1—C6—C9	120.9 (2)
O8—P2—O6	111.54 (9)	C5—C6—C9	123.2 (2)
O7—P2—O6	105.11 (9)	C8—C7—C2	116.7 (3)
O8—P2—O5	104.66 (8)	C8—C7—H7A	108.1
O7—P2—O5	111.86 (9)	C2—C7—H7A	108.1
O6—P2—O5	107.82 (9)	C8—C7—H7B	108.1
P1—O2—H2	109.5	C2—C7—H7B	108.1
P1—O3—H3	109.5	H7A—C7—H7B	107.3
P1—O4—H4	109.5	C7—C8—H8A	109.5
P2—O5—H5	109.5	C7—C8—H8B	109.5
P2—O6—H6	109.5	H8A—C8—H8B	109.5
C1—N1—H1A	109.5	C7—C8—H8C	109.5
C1—N1—H1B	109.5	H8A—C8—H8C	109.5
H1A—N1—H1B	109.5	H8B—C8—H8C	109.5
C1—N1—H1C	109.5	C10—C9—C6	117.8 (2)
H1A—N1—H1C	109.5	C10—C9—H9A	107.8
H1B—N1—H1C	109.5	C6—C9—H9A	107.8
C2—C1—C6	124.9 (2)	C10—C9—H9B	107.8
C2—C1—N1	118.8 (2)	C6—C9—H9B	107.8
C6—C1—N1	116.4 (2)	H9A—C9—H9B	107.2
C1—C2—C3	116.4 (2)	C9—C10—H10A	109.5
C1—C2—C7	120.6 (2)	C9—C10—H10B	109.5
C3—C2—C7	123.0 (2)	H10A—C10—H10B	109.5
C4—C3—C2	120.8 (3)	C9—C10—H10C	109.5
C4—C3—H3A	119.6	H10A—C10—H10C	109.5
C2—C3—H3A	119.6	H10B—C10—H10C	109.5
C5—C4—C3	120.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.84	2.540 (2)	142.
O3—H3···O8ii	0.82	1.72	2.520 (2)	166.
O4—H4···O7iii	0.82	1.74	2.521 (2)	158.
O5—H5···O1	0.82	1.86	2.664 (2)	165.
O6—H6···O7ii	0.82	1.76	2.577 (2)	171.
N1—H1A···O6	0.89	2.18	2.927 (2)	141.
N1—H1B···O8iv	0.89	1.89	2.772 (2)	172.
N1—H1C···O2	0.89	1.98	2.861 (3)	168.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.84	2.540 (2)	142
O3—H3⋯O8ii	0.82	1.72	2.520 (2)	166
O4—H4⋯O7iii	0.82	1.74	2.521 (2)	158
O5—H5⋯O1	0.82	1.86	2.664 (2)	165
O6—H6⋯O7ii	0.82	1.76	2.577 (2)	171
N1—H1A⋯O6	0.89	2.18	2.927 (2)	141
N1—H1B⋯O8iv	0.89	1.89	2.772 (2)	172
N1—H1C⋯O2	0.89	1.98	2.861 (3)	168

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