Literature DB >> 21583955

2-Methyl-anilinium dihydrogen phosphate-phospho-ric acid (1/1).

Hamed Khemiri¹, Samah Akriche, Mohamed Rzaigui.

Abstract

In the title compound, C(7)H(10)N(+)·H(2)PO(4) (-)·H(3)PO(4), there is a clear distinction between the P-O/P=O and P-OH bond lengths. In the crystal, the H(2)PO(4) (-) anions and H(3)PO(4) mol-ecules are linked by O-H⋯O hydrogen bonds, leading to layers propagating in the bc plane. The organic cations are located between these layers and inter-act with them by way of N-H⋯O hydrogen bonds.

Entities: Chemical Disease Gene

Year: 2009 PMID： 21583955 PMCID： PMC2977818 DOI： 10.1107/S1600536809014536

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For related structures, see: Akriche & Rzaigui (2000 ▶); Zaccaro et al. (1996 ▶). For background, see: Desiraju (1995 ▶).

Experimental

Crystal data

C7H10N+·H2PO4 −·H3PO4 M = 303.14 Monoclinic, a = 10.8769 (10) Å b = 7.938 (4) Å c = 15.302 (3) Å β = 91.57 (2)° V = 1320.7 (7) Å3 Z = 4 Ag Kα radiation μ = 0.19 mm−1 T = 298 K 0.37 × 0.31 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer Absorption correction: none 5416 measured reflections 5250 independent reflections 4134 reflections with I > 2σ(I) R int = 0.013 2 standard reflections frequency: 120 min intensity decay: 18%

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.092 S = 1.08 5250 reflections 170 parameters H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.41 e Å−3 Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND Brandenburg (2005); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809014536/hb2955sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014536/hb2955Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₇H₁₀N⁺·H₂PO₄⁻·H₃PO₄	F(000) = 632
M_r = 303.14	D_x = 1.525 Mg m⁻³
Monoclinic, P2₁/c	Ag Kα radiation, λ = 0.56085 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.8769 (10) Å	θ = 8–12°
b = 7.938 (4) Å	µ = 0.19 mm⁻¹
c = 15.302 (3) Å	T = 298 K
β = 91.57 (2)°	Prism, colorless
V = 1320.7 (7) Å³	0.37 × 0.31 × 0.25 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	θ_max = 26.0°, θ_min = 2.1°
Radiation source: fine-focus sealed tube	h = −16→16
Nonprofiled ω scans	k = 0→12
5416 measured reflections	l = 0→23
5250 independent reflections	2 standard reflections every 120 min
4134 reflections with I > 2σ(I)	intensity decay: 18%
R_int = 0.013

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0493P)² + 0.181P] where P = (F_o² + 2F_c²)/3
5250 reflections	(Δ/σ)_max = 0.001
170 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.41 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	U_iso*/U_eq
P1	0.08064 (3)	0.43847 (3)	0.736601 (16)	0.02322 (6)
P2	0.10749 (3)	0.71819 (3)	0.986049 (17)	0.02487 (7)
O1	−0.06037 (8)	0.40074 (11)	0.74454 (6)	0.03314 (17)
H1	−0.0695	0.3079	0.7670	0.050*
O2	0.13778 (8)	0.28822 (10)	0.68641 (6)	0.03396 (18)
H2	0.0974	0.2708	0.6413	0.051*
O3	0.14542 (9)	0.44285 (11)	0.82411 (5)	0.03420 (18)
O4	0.08566 (9)	0.59919 (10)	0.68413 (6)	0.03335 (18)
O5	0.19612 (9)	0.70906 (12)	0.90923 (6)	0.0394 (2)
H5	0.1806	0.6250	0.8798	0.059*
O6	0.14555 (9)	0.58760 (11)	1.05701 (6)	0.0372 (2)
H6	0.1003	0.5052	1.0530	0.056*
O7	0.13831 (9)	0.89278 (10)	1.02544 (5)	0.03362 (18)
H7	0.1232	0.8928	1.0776	0.050*
O8	−0.02457 (8)	0.69700 (11)	0.95881 (6)	0.03445 (18)
N1	0.20745 (9)	0.11752 (14)	0.87628 (7)	0.0355 (2)
H1A	0.1698	0.0513	0.8370	0.053*
H1B	0.1808	0.2228	0.8695	0.053*
H1C	0.1910	0.0818	0.9298	0.053*
C1	0.34057 (12)	0.11198 (18)	0.86394 (10)	0.0400 (3)
C2	0.41777 (14)	0.1876 (2)	0.92552 (12)	0.0517 (4)
C3	0.54313 (16)	0.1826 (3)	0.90905 (19)	0.0797 (7)
H3C	0.5986	0.2305	0.9492	0.096*
C4	0.58628 (19)	0.1090 (4)	0.8354 (2)	0.0930 (8)
H4C	0.6702	0.1099	0.8252	0.112*
C5	0.5070 (2)	0.0340 (4)	0.7763 (2)	0.0930 (8)
H5C	0.5374	−0.0182	0.7269	0.112*
C6	0.38195 (18)	0.0357 (3)	0.78970 (14)	0.0643 (5)
H6C	0.3272	−0.0136	0.7496	0.077*
C7	0.3703 (2)	0.2703 (4)	1.00570 (16)	0.0795 (7)
H7A	0.3238	0.1902	1.0382	0.119*
H7B	0.3185	0.3634	0.9890	0.119*
H7C	0.4382	0.3104	1.0413	0.119*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.03254 (13)	0.01806 (11)	0.01906 (11)	0.00111 (9)	0.00062 (9)	−0.00078 (8)
P2	0.03360 (14)	0.02046 (11)	0.02043 (11)	−0.00449 (9)	−0.00143 (9)	0.00068 (9)
O1	0.0333 (4)	0.0282 (4)	0.0379 (4)	−0.0007 (3)	0.0019 (3)	0.0069 (3)
O2	0.0416 (5)	0.0282 (4)	0.0317 (4)	0.0095 (3)	−0.0053 (3)	−0.0105 (3)
O3	0.0498 (5)	0.0286 (4)	0.0238 (4)	−0.0003 (3)	−0.0071 (3)	−0.0040 (3)
O4	0.0491 (5)	0.0222 (3)	0.0292 (4)	0.0023 (3)	0.0101 (3)	0.0047 (3)
O5	0.0494 (5)	0.0385 (5)	0.0309 (4)	−0.0126 (4)	0.0104 (4)	−0.0106 (4)
O6	0.0437 (5)	0.0286 (4)	0.0387 (5)	−0.0069 (3)	−0.0126 (4)	0.0104 (3)
O7	0.0533 (5)	0.0225 (3)	0.0252 (4)	−0.0075 (3)	0.0034 (3)	−0.0037 (3)
O8	0.0366 (4)	0.0299 (4)	0.0363 (4)	−0.0056 (3)	−0.0082 (3)	0.0101 (3)
N1	0.0315 (5)	0.0339 (5)	0.0409 (5)	−0.0036 (4)	−0.0042 (4)	0.0062 (4)
C1	0.0318 (5)	0.0355 (6)	0.0526 (8)	0.0023 (5)	−0.0013 (5)	0.0065 (6)
C2	0.0360 (6)	0.0522 (9)	0.0662 (10)	0.0007 (6)	−0.0108 (6)	−0.0003 (8)
C3	0.0317 (7)	0.0912 (16)	0.1154 (19)	0.0004 (9)	−0.0107 (10)	−0.0069 (14)
C4	0.0366 (8)	0.123 (2)	0.120 (2)	0.0120 (11)	0.0082 (11)	−0.0074 (19)
C5	0.0630 (13)	0.113 (2)	0.105 (2)	0.0177 (13)	0.0272 (13)	−0.0215 (17)
C6	0.0528 (9)	0.0726 (12)	0.0677 (11)	0.0044 (9)	0.0066 (8)	−0.0128 (10)
C7	0.0610 (12)	0.1016 (18)	0.0752 (14)	−0.0020 (11)	−0.0123 (10)	−0.0313 (13)

P1—O3	1.4964 (9)	N1—H1C	0.8900
P1—O4	1.5092 (10)	C1—C6	1.374 (2)
P1—O2	1.5571 (9)	C1—C2	1.382 (2)
P1—O1	1.5707 (9)	C2—C3	1.394 (2)
P2—O8	1.4942 (9)	C2—C7	1.496 (3)
P2—O5	1.5422 (10)	C3—C4	1.365 (4)
P2—O7	1.5445 (10)	C3—H3C	0.9300
P2—O6	1.5493 (10)	C4—C5	1.368 (4)
O1—H1	0.8200	C4—H4C	0.9300
O2—H2	0.8200	C5—C6	1.381 (3)
O5—H5	0.8200	C5—H5C	0.9300
O6—H6	0.8200	C6—H6C	0.9300
O7—H7	0.8200	C7—H7A	0.9600
N1—C1	1.4659 (16)	C7—H7B	0.9600
N1—H1A	0.8900	C7—H7C	0.9600
N1—H1B	0.8900

O3—P1—O4	115.69 (5)	C6—C1—N1	117.83 (14)
O3—P1—O2	105.94 (5)	C2—C1—N1	118.88 (14)
O4—P1—O2	111.37 (6)	C1—C2—C3	116.33 (18)
O3—P1—O1	111.84 (6)	C1—C2—C7	122.21 (15)
O4—P1—O1	104.60 (5)	C3—C2—C7	121.46 (18)
O2—P1—O1	107.21 (5)	C4—C3—C2	121.5 (2)
O8—P2—O5	113.47 (6)	C4—C3—H3C	119.3
O8—P2—O7	113.99 (6)	C2—C3—H3C	119.3
O5—P2—O7	101.89 (5)	C3—C4—C5	120.51 (19)
O8—P2—O6	110.89 (5)	C3—C4—H4C	119.7
O5—P2—O6	110.01 (6)	C5—C4—H4C	119.7
O7—P2—O6	106.02 (6)	C4—C5—C6	120.2 (2)
P1—O1—H1	109.5	C4—C5—H5C	119.9
P1—O2—H2	109.5	C6—C5—H5C	119.9
P2—O5—H5	109.5	C1—C6—C5	118.3 (2)
P2—O6—H6	109.5	C1—C6—H6C	120.9
P2—O7—H7	109.5	C5—C6—H6C	120.9
C1—N1—H1A	109.5	C2—C7—H7A	109.5
C1—N1—H1B	109.5	C2—C7—H7B	109.5
H1A—N1—H1B	109.5	H7A—C7—H7B	109.5
C1—N1—H1C	109.5	C2—C7—H7C	109.5
H1A—N1—H1C	109.5	H7A—C7—H7C	109.5
H1B—N1—H1C	109.5	H7B—C7—H7C	109.5
C6—C1—C2	123.26 (15)

C6—C1—C2—C3	−0.3 (3)	C2—C3—C4—C5	−1.6 (5)
N1—C1—C2—C3	−178.19 (16)	C3—C4—C5—C6	1.6 (5)
C6—C1—C2—C7	179.8 (2)	C2—C1—C6—C5	0.3 (3)
N1—C1—C2—C7	1.9 (3)	N1—C1—C6—C5	178.2 (2)
C1—C2—C3—C4	0.9 (3)	C4—C5—C6—C1	−0.9 (4)
C7—C2—C3—C4	−179.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.82	1.83	2.6483 (16)	178
O2—H2···O8ⁱ	0.82	1.80	2.6132 (13)	170
O5—H5···O3	0.82	1.72	2.5351 (15)	176
O6—H6···O8ⁱⁱ	0.82	1.81	2.6223 (16)	170
O7—H7···O4ⁱⁱⁱ	0.82	1.69	2.5109 (13)	177
N1—H1A···O1ⁱ	0.89	2.08	2.9627 (16)	172
N1—H1B···O3	0.89	1.91	2.7808 (19)	164
N1—H1C···O7^iv	0.89	2.18	3.0086 (15)	154

Table 1

Selected bond lengths (Å)

P1—O3	1.4964 (9)
P1—O4	1.5092 (10)
P1—O2	1.5571 (9)
P1—O1	1.5707 (9)
P2—O8	1.4942 (9)
P2—O5	1.5422 (10)
P2—O7	1.5445 (10)
P2—O6	1.5493 (10)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.82	1.83	2.6483 (16)	178
O2—H2⋯O8ⁱ	0.82	1.80	2.6132 (13)	170
O5—H5⋯O3	0.82	1.72	2.5351 (15)	176
O6—H6⋯O8ⁱⁱ	0.82	1.81	2.6223 (16)	170
O7—H7⋯O4ⁱⁱⁱ	0.82	1.69	2.5109 (13)	177
N1—H1A⋯O1ⁱ	0.89	2.08	2.9627 (16)	172
N1—H1B⋯O3	0.89	1.91	2.7808 (19)	164
N1—H1C⋯O7^iv	0.89	2.18	3.0086 (15)	154

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

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