Dicyclo­hexyl­ammonium hydrogen phenyl­phospho­nate

Diop, T.; Diop, L.; Maris, T.; Stoeckli-Evans, H.

doi:10.1107/S160053681201553X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1432

doi:10.1107/S160053681201553X

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Dicyclohexylammonium hydrogen phenylphosphonate

Tidiane Diop,^a ^* Libasse Diop,^a Thierry Maris ^b and Helen Stoeckli-Evans ^c

^aLaboratoire de Chimie Minerale et Analytique, Departement de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, ^bDepartement de Chimie, Université de Montreal, CP 6128, Succ. Centre-Ville, Montreal, Quebec, Canada H3C 3J7, and ^cInstitute of Physics, University of Neuchâtel, rue Emile-Argand 11, CH-2000 Neuchâtel, Switzerland
^*Correspondence e-mail: tijchimia@yahoo.fr

(Received 30 March 2012; accepted 10 April 2012; online 18 April 2012)

In the title salt, [(C₆H₁₁)₂NH₂]⁺·[C₆H₅PO₂(OH)]⁻, the anion is monodeprotonated and acts as both a hydrogen-bond donor and acceptor. The anions are linked by pairs of O—H⋯O interactions, forming inversion dimers with R₂²(8) ring motifs. These dimers are bridged by two dicyclohexylaminium cations via pairs of N—H⋯O hydrogen bonds, giving R₄⁴(12) ring motifs, forming chains propagating along [010]. The chains are bridged by C—H⋯O interactions, forming a two-dimensional network lying parallel to (101).

Related literature

For the crystal structure of phenylphosphonic acid, see: Weakley (1976 ). For the crystal structure of anilinium phenylphosphonate, see: Mahmoudkhani & Langer (2002 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₂H₂₄N⁺·C₆H₆O₃P⁻
M_r = 339.40
Monoclinic, P 2₁ /n
a = 13.3212 (4) Å
b = 8.9093 (3) Å
c = 16.0670 (5) Å
β = 104.385 (1)°
V = 1847.09 (10) Å³
Z = 4
Cu Kα radiation
μ = 1.43 mm⁻¹
T = 150 K
0.16 × 0.12 × 0.08 mm

Data collection

Bruker Microstar diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.749, T_max = 0.892
21802 measured reflections
3456 independent reflections
3221 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.098
S = 1.08
3456 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1ⁱ	0.84	1.75	2.5920 (13)	175
N1—H1A⋯O1	0.92	1.86	2.7520 (14)	161
N1—H1B⋯O2ⁱⁱ	0.92	1.81	2.6897 (15)	159
C18—H18A⋯O3ⁱⁱⁱ	0.99	2.52	3.3019 (16)	136
C18—H18B⋯O2ⁱⁱ	0.99	2.52	3.2693 (16)	133
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681201553X/hb6721sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201553X/hb6721Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201553X/hb6721Isup3.cml

checkCIF report

Comment top

In the title salt (Fig. 1), the hydrogen phenylphosphonate anion is unequivocally tetrahedral, with three oxygen atoms and a phenyl group; O2—P1—O1 116.59 (5)°, O3—P1—C1 104.45 (5)°. The P—O distances are different [1.4870 (10) Å for P═O, 1.5134 (9) Å for P-O^-, and 1.574 (3) Å for bond P-O(H)]. This is similar to the situation in the crystal structure of the parent phenylphosphonic acid PhPO₃H₂ (Weakley, 1976), with bond distances of 1.496 Å for P═O and 1.545 Å for P—O(H).

In the crystal, the anions are linked by a pair of O-H···O hydrogen bonds to form inversion dimers with a ring motif of R²₂(8) (Bernstein et al., 1995; Table 1 and Fig. 2). These dimers are linked by two dicyclohexylaminium cations, via pairs of N-H···O hydrogen bonds forming a ring motif of R⁴₄(12), to form chains propagating along [010], as shown in Table 1 and Fig. 2. A similar chain arrangement has been observed in the crystal structure of anilinium phenylphosphonate (Mahmoudkhani & Langer, 2002). In the title compound the chains are linked by C-H···O interactions to form a two-dimensional network that lies parallel to (101); see Table 1 and Fig. 2.

Related literature top

For the crystal structure of phenylphosphonic acid, see: Weakley (1976). For the crystal structure of anilinium phenylphosphonate, see: Mahmoudkhani & Langer (2002). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

When dicyclohexylamine was allowed to react with phenylphosphonic acid in an equimolar ratio (1:1) in water, a precipitate was obtained and filtered [Yield: 83%; M.p: 448 K]. The filtrate was allowed to evaporate at 333 K, giving colourless block-like crystals of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title salt. Displacement ellipsoids are drawn at the 50% probability level [an N-H···O hydrogen bond is shown as a dashed line].
	Fig. 2. A view of the crystal packing of the title salt. The O-H···O and N-H···O hydrogen bonds, and the C-H···O interactions are shown as dashed cyan lines (see Table 1 for details; H atoms not involved in these interactions have been omitted for clarity).

dicyclohexylammonium hydrogen phenylphosphonate top

Crystal data top

C₁₂H₂₄N⁺·C₆H₆O₃P⁻	F(000) = 736
M_r = 339.40	D_x = 1.220 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 10987 reflections
a = 13.3212 (4) Å	θ = 3.9–69.5°
b = 8.9093 (3) Å	µ = 1.43 mm⁻¹
c = 16.0670 (5) Å	T = 150 K
β = 104.385 (1)°	Block, colourless
V = 1847.09 (10) Å³	0.16 × 0.12 × 0.08 mm
Z = 4

Data collection top

Bruker Microstar diffractometer	3456 independent reflections
Radiation source: Rotating Anode	3221 reflections with I > 2σ(I)
Helios optics monochromator	R_int = 0.045
Detector resolution: 8.3 pixels mm^-1	θ_max = 70.0°, θ_min = 3.9°
ω scans	h = −15→16
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	k = −10→10
T_min = 0.749, T_max = 0.892	l = −19→17
21802 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0485P)² + 0.5837P] where P = (F_o² + 2F_c²)/3
3456 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₂H₂₄N⁺·C₆H₆O₃P⁻	V = 1847.09 (10) Å³
M_r = 339.40	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 13.3212 (4) Å	µ = 1.43 mm⁻¹
b = 8.9093 (3) Å	T = 150 K
c = 16.0670 (5) Å	0.16 × 0.12 × 0.08 mm
β = 104.385 (1)°

Data collection top

Bruker Microstar diffractometer	3456 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3221 reflections with I > 2σ(I)
T_min = 0.749, T_max = 0.892	R_int = 0.045
21802 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.08	Δρ_max = 0.34 e Å⁻³
3456 reflections	Δρ_min = −0.34 e Å⁻³
210 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
N1	0.61697 (8)	0.08819 (12)	0.61698 (7)	0.0241 (3)
C7	0.78359 (11)	0.20505 (17)	0.60436 (11)	0.0360 (4)
C8	0.88185 (13)	0.17940 (19)	0.57279 (13)	0.0474 (6)
C9	0.85691 (14)	0.1191 (2)	0.48160 (12)	0.0504 (6)
C10	0.79476 (14)	−0.02535 (19)	0.47509 (11)	0.0456 (6)
C11	0.69609 (12)	−0.00267 (17)	0.50547 (9)	0.0347 (4)
C12	0.71952 (10)	0.06220 (15)	0.59617 (9)	0.0270 (4)
C13	0.61555 (10)	0.16079 (14)	0.70110 (8)	0.0246 (4)
C14	0.50257 (10)	0.18592 (16)	0.70178 (9)	0.0297 (4)
C15	0.49544 (11)	0.25630 (18)	0.78668 (10)	0.0359 (4)
C16	0.54933 (12)	0.15792 (18)	0.86212 (10)	0.0375 (5)
C17	0.66214 (11)	0.13042 (17)	0.86139 (9)	0.0335 (4)
C18	0.67143 (10)	0.06407 (15)	0.77601 (8)	0.0285 (4)
P1	0.48868 (2)	0.32919 (3)	0.40858 (2)	0.0235 (1)
O1	0.52613 (7)	0.31140 (10)	0.50502 (6)	0.0267 (3)
O2	0.43638 (8)	0.19710 (11)	0.35992 (6)	0.0353 (3)
O3	0.41421 (7)	0.46904 (10)	0.38831 (6)	0.0278 (3)
C1	0.59865 (10)	0.38079 (15)	0.36779 (8)	0.0267 (4)
C2	0.61401 (14)	0.31648 (17)	0.29338 (10)	0.0401 (5)
C3	0.69755 (16)	0.3597 (2)	0.26150 (12)	0.0534 (7)
C4	0.76585 (14)	0.46728 (19)	0.30332 (13)	0.0492 (6)
C5	0.75229 (12)	0.53178 (18)	0.37773 (11)	0.0401 (5)
C6	0.66913 (11)	0.48883 (16)	0.40993 (9)	0.0309 (4)
H1A	0.57730	0.14630	0.57380	0.0360*
H1B	0.58430	−0.00320	0.61490	0.0360*
H7A	0.80310	0.23750	0.66520	0.0430*
H7B	0.74170	0.28580	0.57010	0.0430*
H8A	0.91990	0.27540	0.57510	0.0570*
H8B	0.92740	0.10730	0.61150	0.0570*
H9A	0.92210	0.09980	0.46440	0.0600*
H9B	0.81670	0.19490	0.44190	0.0600*
H10A	0.83780	−0.10390	0.51050	0.0550*
H10B	0.77630	−0.06020	0.41470	0.0550*
H11A	0.66020	−0.10020	0.50450	0.0420*
H11B	0.64910	0.06620	0.46550	0.0420*
H12	0.75910	−0.01410	0.63710	0.0320*
H13	0.65120	0.26030	0.70480	0.0290*
H14A	0.46530	0.08880	0.69370	0.0360*
H14B	0.46920	0.25290	0.65370	0.0360*
H15A	0.52820	0.35680	0.79260	0.0430*
H15B	0.42170	0.26900	0.78700	0.0430*
H16A	0.51270	0.06060	0.85890	0.0450*
H16B	0.54650	0.20750	0.91660	0.0450*
H17A	0.69400	0.06080	0.90860	0.0400*
H17B	0.70060	0.22640	0.87170	0.0400*
H18A	0.74550	0.05610	0.77590	0.0340*
H18B	0.64150	−0.03820	0.76940	0.0340*
H2	0.56710	0.24240	0.26400	0.0480*
H3	0.70750	0.31480	0.21050	0.0640*
H3A	0.43610	0.53690	0.42460	0.0420*
H4	0.82240	0.49710	0.28090	0.0590*
H5	0.79970	0.60540	0.40690	0.0480*
H6	0.66000	0.53350	0.46130	0.0370*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0276 (5)	0.0192 (5)	0.0238 (5)	−0.0008 (4)	0.0032 (4)	0.0000 (4)
C7	0.0332 (7)	0.0271 (7)	0.0489 (9)	−0.0022 (6)	0.0124 (7)	−0.0015 (6)
C8	0.0360 (8)	0.0408 (10)	0.0700 (12)	−0.0010 (7)	0.0217 (8)	0.0067 (8)
C9	0.0545 (10)	0.0475 (10)	0.0595 (11)	0.0129 (8)	0.0339 (9)	0.0174 (8)
C10	0.0634 (11)	0.0403 (9)	0.0396 (9)	0.0131 (8)	0.0251 (8)	0.0038 (7)
C11	0.0468 (8)	0.0285 (7)	0.0297 (7)	0.0028 (6)	0.0111 (6)	−0.0007 (6)
C12	0.0302 (7)	0.0217 (6)	0.0292 (7)	0.0024 (5)	0.0074 (5)	0.0004 (5)
C13	0.0286 (7)	0.0185 (6)	0.0254 (7)	−0.0005 (5)	0.0044 (5)	−0.0015 (5)
C14	0.0285 (7)	0.0290 (7)	0.0302 (7)	0.0033 (5)	0.0046 (6)	0.0043 (5)
C15	0.0349 (7)	0.0358 (8)	0.0385 (8)	0.0055 (6)	0.0121 (6)	−0.0022 (6)
C16	0.0432 (8)	0.0409 (9)	0.0292 (8)	−0.0010 (7)	0.0105 (6)	−0.0028 (6)
C17	0.0391 (8)	0.0326 (8)	0.0256 (7)	0.0007 (6)	0.0018 (6)	−0.0028 (6)
C18	0.0316 (7)	0.0257 (7)	0.0245 (7)	0.0035 (5)	0.0001 (5)	−0.0016 (5)
P1	0.0288 (2)	0.0179 (2)	0.0229 (2)	−0.0024 (1)	0.0046 (1)	0.0004 (1)
O1	0.0342 (5)	0.0218 (5)	0.0240 (5)	0.0016 (4)	0.0072 (4)	0.0029 (3)
O2	0.0477 (6)	0.0236 (5)	0.0325 (5)	−0.0097 (4)	0.0060 (5)	−0.0035 (4)
O3	0.0270 (5)	0.0248 (5)	0.0285 (5)	0.0002 (4)	0.0008 (4)	0.0000 (4)
C1	0.0343 (7)	0.0201 (6)	0.0258 (7)	0.0042 (5)	0.0079 (5)	0.0043 (5)
C2	0.0615 (10)	0.0278 (8)	0.0359 (8)	−0.0015 (7)	0.0216 (7)	−0.0011 (6)
C3	0.0848 (14)	0.0386 (9)	0.0523 (11)	0.0060 (9)	0.0464 (10)	0.0020 (8)
C4	0.0544 (10)	0.0389 (9)	0.0673 (12)	0.0076 (8)	0.0396 (9)	0.0146 (8)
C5	0.0342 (7)	0.0362 (8)	0.0523 (10)	−0.0008 (6)	0.0151 (7)	0.0093 (7)
C6	0.0313 (7)	0.0299 (7)	0.0318 (7)	0.0003 (6)	0.0084 (6)	0.0036 (6)

Geometric parameters (Å, º) top

P1—O1	1.5136 (10)	C10—H10A	0.9900
P1—O2	1.4869 (10)	C10—H10B	0.9900
P1—O3	1.5755 (10)	C11—H11A	0.9900
P1—C1	1.8066 (14)	C11—H11B	0.9900
O3—H3A	0.8400	C12—H12	1.0000
N1—C12	1.5029 (18)	C13—H13	1.0000
N1—C13	1.5027 (17)	C14—H14B	0.9900
N1—H1A	0.9200	C14—H14A	0.9900
N1—H1B	0.9200	C15—H15A	0.9900
C7—C12	1.520 (2)	C15—H15B	0.9900
C7—C8	1.534 (2)	C16—H16A	0.9900
C8—C9	1.518 (3)	C16—H16B	0.9900
C9—C10	1.520 (3)	C17—H17A	0.9900
C10—C11	1.525 (2)	C17—H17B	0.9900
C11—C12	1.526 (2)	C18—H18B	0.9900
C13—C14	1.5243 (19)	C18—H18A	0.9900
C13—C18	1.5166 (18)	C1—C6	1.397 (2)
C14—C15	1.526 (2)	C1—C2	1.386 (2)
C15—C16	1.523 (2)	C2—C3	1.390 (3)
C16—C17	1.526 (2)	C3—C4	1.376 (3)
C17—C18	1.5267 (19)	C4—C5	1.378 (3)
C7—H7A	0.9900	C5—C6	1.388 (2)
C7—H7B	0.9900	C2—H2	0.9500
C8—H8B	0.9900	C3—H3	0.9500
C8—H8A	0.9900	C4—H4	0.9500
C9—H9A	0.9900	C5—H5	0.9500
C9—H9B	0.9900	C6—H6	0.9500

O1—P1—O2	116.59 (5)	C12—C11—H11B	109.00
O1—P1—O3	108.96 (5)	H11A—C11—H11B	108.00
O1—P1—C1	107.90 (6)	N1—C12—H12	109.00
O2—P1—O3	109.18 (6)	C11—C12—H12	109.00
O2—P1—C1	109.08 (6)	C7—C12—H12	109.00
O3—P1—C1	104.45 (6)	C18—C13—H13	109.00
P1—O3—H3A	109.00	N1—C13—H13	109.00
C12—N1—C13	118.80 (10)	C14—C13—H13	109.00
H1A—N1—H1B	107.00	C15—C14—H14A	110.00
C12—N1—H1A	108.00	C13—C14—H14B	110.00
C12—N1—H1B	108.00	C13—C14—H14A	110.00
C13—N1—H1B	108.00	C15—C14—H14B	110.00
C13—N1—H1A	108.00	H14A—C14—H14B	108.00
C8—C7—C12	110.71 (13)	H15A—C15—H15B	108.00
C7—C8—C9	111.83 (15)	C14—C15—H15B	110.00
C8—C9—C10	110.55 (15)	C16—C15—H15A	110.00
C9—C10—C11	111.34 (14)	C14—C15—H15A	109.00
C10—C11—C12	111.58 (13)	C16—C15—H15B	109.00
C7—C12—C11	112.15 (12)	C15—C16—H16B	109.00
N1—C12—C11	106.81 (11)	C15—C16—H16A	109.00
N1—C12—C7	111.94 (11)	H16A—C16—H16B	108.00
C14—C13—C18	111.63 (11)	C17—C16—H16A	109.00
N1—C13—C14	107.62 (10)	C17—C16—H16B	109.00
N1—C13—C18	110.85 (10)	C16—C17—H17B	109.00
C13—C14—C15	110.35 (11)	C16—C17—H17A	109.00
C14—C15—C16	110.69 (13)	C18—C17—H17A	109.00
C15—C16—C17	110.90 (13)	C18—C17—H17B	109.00
C16—C17—C18	111.65 (12)	H17A—C17—H17B	108.00
C13—C18—C17	111.08 (11)	C13—C18—H18A	109.00
C8—C7—H7B	110.00	C13—C18—H18B	109.00
C12—C7—H7A	110.00	C17—C18—H18A	109.00
C12—C7—H7B	109.00	C17—C18—H18B	109.00
C8—C7—H7A	109.00	H18A—C18—H18B	108.00
H7A—C7—H7B	108.00	P1—C1—C2	120.96 (11)
H8A—C8—H8B	108.00	C2—C1—C6	118.53 (13)
C7—C8—H8A	109.00	P1—C1—C6	120.50 (10)
C7—C8—H8B	109.00	C1—C2—C3	120.44 (15)
C9—C8—H8B	109.00	C2—C3—C4	120.38 (17)
C9—C8—H8A	109.00	C3—C4—C5	120.04 (18)
C8—C9—H9B	110.00	C4—C5—C6	119.81 (15)
C8—C9—H9A	110.00	C1—C6—C5	120.80 (13)
H9A—C9—H9B	108.00	C1—C2—H2	120.00
C10—C9—H9A	110.00	C3—C2—H2	120.00
C10—C9—H9B	110.00	C2—C3—H3	120.00
C9—C10—H10B	109.00	C4—C3—H3	120.00
C9—C10—H10A	109.00	C3—C4—H4	120.00
C11—C10—H10A	109.00	C5—C4—H4	120.00
C11—C10—H10B	109.00	C4—C5—H5	120.00
H10A—C10—H10B	108.00	C6—C5—H5	120.00
C10—C11—H11A	109.00	C1—C6—H6	120.00
C10—C11—H11B	109.00	C5—C6—H6	120.00
C12—C11—H11A	109.00

O3—P1—C1—C2	−106.84 (12)	C10—C11—C12—N1	176.67 (12)
O1—P1—C1—C6	−43.88 (13)	N1—C13—C14—C15	178.67 (11)
O2—P1—C1—C6	−171.43 (11)	C14—C13—C18—C17	−55.08 (15)
O3—P1—C1—C6	71.95 (12)	C18—C13—C14—C15	56.83 (15)
O1—P1—C1—C2	137.33 (12)	N1—C13—C18—C17	−175.05 (11)
O2—P1—C1—C2	9.78 (14)	C13—C14—C15—C16	−57.40 (16)
C12—N1—C13—C18	−62.64 (14)	C14—C15—C16—C17	56.75 (16)
C13—N1—C12—C11	−176.40 (11)	C15—C16—C17—C18	−55.13 (16)
C12—N1—C13—C14	175.04 (11)	C16—C17—C18—C13	54.13 (16)
C13—N1—C12—C7	−53.28 (15)	P1—C1—C2—C3	178.46 (13)
C12—C7—C8—C9	55.25 (18)	C6—C1—C2—C3	−0.4 (2)
C8—C7—C12—N1	−173.44 (13)	P1—C1—C6—C5	−178.34 (12)
C8—C7—C12—C11	−53.39 (17)	C2—C1—C6—C5	0.5 (2)
C7—C8—C9—C10	−56.75 (19)	C1—C2—C3—C4	−0.2 (3)
C8—C9—C10—C11	56.27 (19)	C2—C3—C4—C5	0.7 (3)
C9—C10—C11—C12	−54.83 (17)	C3—C4—C5—C6	−0.5 (3)
C10—C11—C12—C7	53.68 (16)	C4—C5—C6—C1	0.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.84	1.75	2.5920 (13)	175
N1—H1A···O1	0.92	1.86	2.7520 (14)	161
N1—H1B···O2ⁱⁱ	0.92	1.81	2.6897 (15)	159
C18—H18A···O3ⁱⁱⁱ	0.99	2.52	3.3019 (16)	136
C18—H18B···O2ⁱⁱ	0.99	2.52	3.2693 (16)	133

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

Experimental details

Crystal data
Chemical formula	C₁₂H₂₄N⁺·C₆H₆O₃P⁻
M_r	339.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	13.3212 (4), 8.9093 (3), 16.0670 (5)
β (°)	104.385 (1)
V (Å³)	1847.09 (10)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.43
Crystal size (mm)	0.16 × 0.12 × 0.08

Data collection
Diffractometer	Bruker Microstar diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.749, 0.892
No. of measured, independent and observed [I > 2σ(I)] reflections	21802, 3456, 3221
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.098, 1.08
No. of reflections	3456
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.34

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.84	1.75	2.5920 (13)	175
N1—H1A···O1	0.92	1.86	2.7520 (14)	161
N1—H1B···O2ⁱⁱ	0.92	1.81	2.6897 (15)	159
C18—H18A···O3ⁱⁱⁱ	0.99	2.52	3.3019 (16)	136
C18—H18B···O2ⁱⁱ	0.99	2.52	3.2693 (16)	133

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

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mahmoudkhani, A. H. & Langer, V. (2002). J. Mol. Struct. 609, 97–108. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Weakley, T. J. R. (1976). Acta Cryst. B32, 2889–2890. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 5| May 2012| Page o1432

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