Dicyclo­hexyl­ammonium 3-[(hy­droxy­meth­yl)carbamo­yl]propano­ate

Rajeswari, S.; Venkatesa Prabhu, G.; Tamilvendan, D.; Stoeckli-Evans, H.

doi:10.1107/S1600536810044958

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3096

https://doi.org/10.1107/S1600536810044958

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Dicyclohexylammonium 3-[(hydroxymethyl)carbamoyl]propanoate

Subadra Rajeswari,^a Ganesan Venkatesa Prabhu,^a ^* Dhanapal Tamilvendan ^a and Helen Stoeckli-Evans ^b

^aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, Tamil Nadu, India, and ^bInstitute of Physics, University of Neuchâtel, rue Emile-Argand 11, CH-2000 Neuchâtel, Switzerland
^*Correspondence e-mail: venkates@nitt.edu,helen.stoeckli-evans@unine.ch

(Received 2 November 2010; accepted 2 November 2010; online 6 November 2010)

The title compound, C₁₂H₂₄N⁺·C₅H₈NO₄⁻, contains one dicyclohexylammonium cation and one 3-[(hydroxymethyl)carbamoyl]propanoate anion in the asymmetric unit. In the crystal, the ions are linked by intermolecular N—H⋯O and O—H⋯O hydrogen bonds, forming chains propagating along [100].

Related literature

For the biological activity of succinimide derivatives, see: Argay et al. (1999 ). For the preparation of the Mannich base 1-[(dicyclohexylamino)methyl]pyrrolidine-2,5-dione, see: Tramontini (1973 ); Tramontini & Angliolini (1990 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₂H₂₄N⁺·C₅H₈NO₄⁻
M_r = 328.45
Monoclinic, P 2₁ /n
a = 5.6844 (5) Å
b = 17.7967 (12) Å
c = 18.4264 (16) Å
β = 95.495 (7)°
V = 1855.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.45 × 0.45 × 0.13 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009 ) T_min = 0.714, T_max = 1.000
11855 measured reflections
3941 independent reflections
2568 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.095
S = 0.93
3941 reflections
225 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.892 (17)	2.597 (17)	3.285 (2)	134.7 (14)
N1—H1A⋯O2ⁱ	0.892 (17)	1.975 (17)	2.8546 (18)	168.7 (15)
N1—H1B⋯O1ⁱⁱ	0.95 (2)	1.80 (2)	2.740 (2)	174.3 (17)
N2—H2N⋯O2ⁱⁱⁱ	0.829 (17)	2.069 (17)	2.8914 (18)	171.1 (16)
O4—H4O⋯O3ⁱⁱⁱ	0.88 (2)	1.78 (2)	2.6423 (16)	166.4 (19)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x-1, y, z.

Data collection: X-AREA (Stoe & Cie, 2009 ); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2009); 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 Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810044958/fj2363sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044958/fj2363Isup2.hkl

checkCIF report

Comment top

The pyrrolidine skeleton occurs in many families of biologically important compounds, and several succinimide derivatives are important in biology due to their antepileptic, anticonvulsive, fungicidal and other pharmalogical properties (Argay et al. 1999). The title compound was obtained during our attempts to prepare the Mannich base 1-((dicyclohexylamino)methyl)pyrrolidine-2,5-dione according to the reported procedure (Tramontini, 1973; Tramontini & Angliolini, 1990). The anion is probably formed by the hydrolysis of succinimide to yield the amino acid, i.e. NH₂COCH₂CH₂COOH. The formation of the the title compound can be accounted for by the reaction of this amino acid with formaldehyde and the subsequent protonation of dicyclohexylamine.

The molecular structure of the title compound is illustrated in Fig. 1. It is compossed of a dicyclohexylammonium cation and a 4-(hydroxymethylamino)-4-oxobutanoate anion. The bond lengths (Allen et al., 1987) and angles are normal.

In the crystal the cations and anions are linked via N—H···O and O—H···O hydrogen bonds involving both the cation and the anion. In this manner hydrogen bonded polymer chains are formed propagating in [100]; see Fig. 2 and Table 1 for details.

Related literature top

For the biological activity of succinimide derivatives, see: Argay et al. (1999). For the preparation of the Mannich base 1-[(dicyclohexylamino)methyl]pyrrolidine-2,5-dione, see: Tramontini (1973); Tramontini & Angliolini (1990). For standard bond lengths, see: Allen et al. (1987).

Experimental top

Dicyclohexylamine (36.2 ml, 0.2M) was added slowly to a solution of succinimide in ethanol (19.8 g, 0.2M). A solution of formaldehyde (40%, 15 ml) was added in drops with continuous stirring of the solution. The yellowish brown compound formed was initially sticky in nature and slowly turned into a stony mass, which was then crushed to form a fine powder. This product was washed several times with acetone and was then dried in the air in an oven at 333 K and recrystallized using water.

Structure description top

For the biological activity of succinimide derivatives, see: Argay et al. (1999). For the preparation of the Mannich base 1-[(dicyclohexylamino)methyl]pyrrolidine-2,5-dione, see: Tramontini (1973); Tramontini & Angliolini (1990). For standard bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-RED32 (Stoe & Cie, 2009); 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 Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A partial view of the crystal packing of the title compound, showing the formation of the N—H···O and O—H···O hydrogen bonded (dashed cyan lines) polymer chain propagating in [100]; see Table 1 for details. H-atoms not involved in hydrogen bonding have been omitted for clarity.

Dicyclohexylammonium 3-[(hydroxymethyl)carbamoyl]propanoate top

Crystal data top

C₁₂H₂₄N⁺·C₅H₈NO₄⁻	F(000) = 720
M_r = 328.45	D_x = 1.176 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7150 reflections
a = 5.6844 (5) Å	θ = 1.6–27.2°
b = 17.7967 (12) Å	µ = 0.08 mm⁻¹
c = 18.4264 (16) Å	T = 173 K
β = 95.495 (7)°	Plate, colourless
V = 1855.5 (3) Å³	0.45 × 0.45 × 0.13 mm
Z = 4

Data collection top

Stoe IPDS-2 diffractometer	3941 independent reflections
Radiation source: fine-focus sealed tube	2568 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
φ and ω scans	θ_max = 26.7°, θ_min = 1.6°
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009)	h = −6→7
T_min = 0.714, T_max = 1.000	k = −22→21
11855 measured reflections	l = −23→23

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0463P)²] where P = (F_o² + 2F_c²)/3
S = 0.93	(Δ/σ)_max < 0.001
3941 reflections	Δρ_max = 0.19 e Å⁻³
225 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0046 (12)

Crystal data top

C₁₂H₂₄N⁺·C₅H₈NO₄⁻	V = 1855.5 (3) Å³
M_r = 328.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.6844 (5) Å	µ = 0.08 mm⁻¹
b = 17.7967 (12) Å	T = 173 K
c = 18.4264 (16) Å	0.45 × 0.45 × 0.13 mm
β = 95.495 (7)°

Data collection top

Stoe IPDS-2 diffractometer	3941 independent reflections
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009)	2568 reflections with I > 2σ(I)
T_min = 0.714, T_max = 1.000	R_int = 0.055
11855 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	Δρ_max = 0.19 e Å⁻³
3941 reflections	Δρ_min = −0.16 e Å⁻³
225 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 e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. The H-atoms could all be located in difference electron-density maps. The NH₂, NH and OH H-atoms were freely refined. O—H = 0.88 (2) Å, N—H = 0.829 (17) - 0.95 (2) Å. The C-bound H-atoms were included in calculated positions and treated as riding: C—H = 0.99 and 1.0 Å for CH₂ and CH H-atoms, respectively, with U_iso(H) = 1.2Ueq (parent C-atom).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.1835 (3)	0.16377 (7)	0.26459 (6)	0.0231 (4)
C1	0.1626 (3)	0.15553 (8)	0.18284 (7)	0.0240 (4)
C2	0.3908 (3)	0.17650 (9)	0.15118 (7)	0.0302 (5)
C3	0.3685 (3)	0.16325 (9)	0.06882 (8)	0.0337 (5)
C4	0.2964 (3)	0.08243 (9)	0.05011 (8)	0.0376 (5)
C5	0.0679 (3)	0.06210 (9)	0.08250 (8)	0.0360 (5)
C6	0.0916 (3)	0.07455 (8)	0.16494 (7)	0.0295 (5)
C7	0.2441 (3)	0.24038 (8)	0.29523 (7)	0.0268 (5)
C8	0.2700 (3)	0.23401 (9)	0.37808 (8)	0.0342 (5)
C9	0.3228 (3)	0.31025 (10)	0.41315 (9)	0.0418 (6)
C10	0.1112 (5)	0.37352 (10)	0.30517 (10)	0.0554 (7)
C11	0.1319 (4)	0.36647 (10)	0.38784 (9)	0.0461 (6)
C12	0.0575 (4)	0.29729 (9)	0.26847 (8)	0.0402 (6)
O1	0.7522 (2)	0.63034 (6)	0.19198 (6)	0.0350 (3)
O2	1.02645 (19)	0.55189 (6)	0.16058 (6)	0.0358 (3)
O3	0.5058 (2)	0.35217 (7)	0.07565 (8)	0.0589 (5)
O4	−0.0493 (2)	0.31104 (7)	0.07088 (6)	0.0382 (4)
N2	0.1841 (2)	0.42193 (8)	0.08447 (7)	0.0317 (4)
C13	0.8158 (3)	0.57440 (8)	0.15773 (7)	0.0256 (4)
C14	0.6297 (3)	0.52971 (9)	0.11060 (8)	0.0292 (5)
C15	0.5506 (3)	0.46122 (9)	0.15209 (8)	0.0334 (5)
C16	0.4109 (3)	0.40679 (9)	0.10178 (8)	0.0324 (5)
C17	0.0415 (3)	0.37297 (9)	0.03501 (8)	0.0341 (5)
H1	0.03410	0.18950	0.16150	0.0290*
H1A	0.290 (3)	0.1313 (10)	0.2847 (8)	0.027 (4)*
H1B	0.038 (4)	0.1508 (10)	0.2824 (10)	0.046 (5)*
H2A	0.52230	0.14590	0.17460	0.0360*
H2B	0.42740	0.23010	0.16150	0.0360*
H3A	0.24910	0.19800	0.04500	0.0400*
H3B	0.52180	0.17420	0.04970	0.0400*
H4A	0.27430	0.07640	−0.00350	0.0450*
H4B	0.42380	0.04790	0.06940	0.0450*
H5A	0.02890	0.00880	0.07180	0.0430*
H5B	−0.06280	0.09340	0.05960	0.0430*
H6A	−0.06090	0.06330	0.18450	0.0350*
H6B	0.21240	0.04000	0.18840	0.0350*
H7	0.39910	0.25640	0.27880	0.0320*
H8A	0.12210	0.21370	0.39470	0.0410*
H8B	0.39970	0.19870	0.39350	0.0410*
H9A	0.33190	0.30530	0.46690	0.0500*
H9B	0.47760	0.32860	0.40000	0.0500*
H10A	0.26100	0.39360	0.28970	0.0670*
H10B	−0.01650	0.40940	0.28940	0.0670*
H11A	0.17100	0.41610	0.41020	0.0550*
H11B	−0.02120	0.34990	0.40380	0.0550*
H12A	−0.09990	0.27950	0.27980	0.0480*
H12B	0.05430	0.30280	0.21490	0.0480*
H2N	0.124 (3)	0.4572 (10)	0.1056 (9)	0.034 (5)*
H4O	−0.195 (4)	0.3219 (13)	0.0796 (11)	0.068 (7)*
H14A	0.69610	0.51300	0.06550	0.0350*
H14B	0.49160	0.56220	0.09640	0.0350*
H15A	0.69130	0.43540	0.17620	0.0400*
H15B	0.45190	0.47800	0.19050	0.0400*
H17A	−0.09140	0.40220	0.01050	0.0410*
H17B	0.13900	0.35450	−0.00300	0.0410*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0259 (7)	0.0221 (7)	0.0210 (6)	0.0028 (6)	0.0002 (5)	0.0016 (5)
C1	0.0289 (8)	0.0222 (7)	0.0202 (7)	0.0021 (7)	−0.0007 (6)	−0.0006 (5)
C2	0.0358 (9)	0.0276 (8)	0.0276 (7)	−0.0042 (7)	0.0051 (6)	−0.0013 (6)
C3	0.0427 (10)	0.0324 (9)	0.0273 (8)	−0.0034 (8)	0.0104 (7)	−0.0013 (6)
C4	0.0526 (11)	0.0335 (9)	0.0278 (8)	0.0002 (8)	0.0096 (7)	−0.0069 (7)
C5	0.0478 (11)	0.0306 (9)	0.0293 (8)	−0.0065 (8)	0.0019 (7)	−0.0077 (6)
C6	0.0362 (9)	0.0245 (8)	0.0277 (7)	−0.0039 (7)	0.0021 (6)	−0.0008 (6)
C7	0.0314 (9)	0.0245 (8)	0.0248 (7)	−0.0036 (7)	0.0041 (6)	−0.0039 (6)
C8	0.0418 (10)	0.0342 (9)	0.0254 (7)	0.0073 (8)	−0.0033 (7)	−0.0040 (6)
C9	0.0476 (11)	0.0452 (10)	0.0319 (8)	−0.0037 (9)	−0.0003 (7)	−0.0125 (8)
C10	0.0968 (18)	0.0235 (9)	0.0439 (10)	0.0069 (10)	−0.0043 (10)	−0.0039 (7)
C11	0.0669 (14)	0.0300 (9)	0.0411 (9)	0.0003 (9)	0.0038 (9)	−0.0121 (7)
C12	0.0623 (12)	0.0257 (9)	0.0305 (8)	0.0080 (9)	−0.0069 (8)	0.0000 (6)
O1	0.0304 (6)	0.0338 (6)	0.0409 (6)	−0.0011 (5)	0.0038 (5)	−0.0132 (5)
O2	0.0265 (6)	0.0311 (6)	0.0485 (6)	0.0006 (5)	−0.0026 (5)	−0.0113 (5)
O3	0.0329 (7)	0.0372 (8)	0.1074 (12)	−0.0028 (6)	0.0107 (7)	−0.0271 (7)
O4	0.0313 (7)	0.0291 (6)	0.0540 (7)	−0.0021 (6)	0.0033 (6)	−0.0010 (5)
N2	0.0303 (8)	0.0277 (7)	0.0366 (7)	−0.0019 (6)	0.0011 (6)	−0.0095 (6)
C13	0.0273 (8)	0.0243 (8)	0.0251 (7)	−0.0030 (7)	0.0017 (6)	0.0007 (6)
C14	0.0288 (9)	0.0250 (8)	0.0325 (8)	−0.0037 (7)	−0.0040 (6)	0.0005 (6)
C15	0.0316 (9)	0.0309 (9)	0.0368 (8)	−0.0074 (8)	−0.0020 (7)	0.0026 (7)
C16	0.0300 (9)	0.0236 (8)	0.0441 (9)	−0.0056 (7)	0.0060 (7)	−0.0008 (7)
C17	0.0357 (9)	0.0335 (9)	0.0330 (8)	−0.0047 (8)	0.0023 (7)	−0.0056 (7)

Geometric parameters (Å, º) top

O1—C13	1.2505 (18)	C3—H3A	0.9900
O2—C13	1.259 (2)	C4—H4B	0.9900
O3—C16	1.232 (2)	C4—H4A	0.9900
O4—C17	1.408 (2)	C5—H5A	0.9900
O4—H4O	0.88 (2)	C5—H5B	0.9900
N1—C1	1.5068 (17)	C6—H6B	0.9900
N1—C7	1.5030 (19)	C6—H6A	0.9900
N1—H1A	0.892 (17)	C7—H7	1.0000
N1—H1B	0.95 (2)	C8—H8B	0.9900
N2—C16	1.326 (2)	C8—H8A	0.9900
N2—C17	1.451 (2)	C9—H9B	0.9900
N2—H2N	0.829 (17)	C9—H9A	0.9900
C1—C6	1.524 (2)	C10—H10B	0.9900
C1—C2	1.519 (2)	C10—H10A	0.9900
C2—C3	1.529 (2)	C11—H11B	0.9900
C3—C4	1.526 (2)	C11—H11A	0.9900
C4—C5	1.524 (2)	C12—H12B	0.9900
C5—C6	1.528 (2)	C12—H12A	0.9900
C7—C12	1.515 (2)	C13—C14	1.526 (2)
C7—C8	1.524 (2)	C14—C15	1.529 (2)
C8—C9	1.520 (2)	C15—C16	1.512 (2)
C9—C11	1.516 (3)	C14—H14A	0.9900
C10—C12	1.533 (2)	C14—H14B	0.9900
C10—C11	1.522 (2)	C15—H15A	0.9900
C1—H1	1.0000	C15—H15B	0.9900
C2—H2A	0.9900	C17—H17A	0.9900
C2—H2B	0.9900	C17—H17B	0.9900
C3—H3B	0.9900

C17—O4—H4O	107.9 (15)	C5—C6—H6A	110.00
C1—N1—C7	117.20 (11)	N1—C7—H7	109.00
C7—N1—H1A	108.0 (11)	C8—C7—H7	109.00
C1—N1—H1A	109.8 (10)	C12—C7—H7	109.00
C1—N1—H1B	109.6 (11)	C7—C8—H8B	109.00
C7—N1—H1B	105.5 (11)	C9—C8—H8A	109.00
H1A—N1—H1B	106.2 (16)	C7—C8—H8A	109.00
C16—N2—C17	120.06 (14)	C9—C8—H8B	109.00
C16—N2—H2N	118.4 (12)	H8A—C8—H8B	108.00
C17—N2—H2N	121.3 (12)	C11—C9—H9B	109.00
N1—C1—C2	111.81 (13)	H9A—C9—H9B	108.00
C2—C1—C6	111.55 (13)	C8—C9—H9A	110.00
N1—C1—C6	107.59 (11)	C8—C9—H9B	110.00
C1—C2—C3	110.53 (13)	C11—C9—H9A	109.00
C2—C3—C4	111.38 (13)	C11—C10—H10B	109.00
C3—C4—C5	110.84 (13)	C12—C10—H10A	109.00
C4—C5—C6	110.95 (13)	C12—C10—H10B	109.00
C1—C6—C5	110.40 (12)	C11—C10—H10A	109.00
N1—C7—C8	107.79 (11)	H10A—C10—H10B	108.00
N1—C7—C12	110.86 (13)	C9—C11—H11B	110.00
C8—C7—C12	111.92 (13)	H11A—C11—H11B	108.00
C7—C8—C9	110.83 (13)	C10—C11—H11A	110.00
C8—C9—C11	110.60 (14)	C9—C11—H11A	110.00
C11—C10—C12	111.20 (14)	C10—C11—H11B	110.00
C9—C11—C10	110.29 (16)	C10—C12—H12B	110.00
C7—C12—C10	110.15 (16)	H12A—C12—H12B	108.00
N1—C1—H1	109.00	C7—C12—H12B	110.00
C6—C1—H1	109.00	C10—C12—H12A	110.00
C2—C1—H1	109.00	C7—C12—H12A	110.00
C3—C2—H2B	110.00	O1—C13—O2	123.51 (14)
C3—C2—H2A	110.00	O1—C13—C14	118.94 (15)
H2A—C2—H2B	108.00	O2—C13—C14	117.55 (13)
C1—C2—H2B	110.00	C13—C14—C15	110.60 (12)
C1—C2—H2A	110.00	C14—C15—C16	111.49 (12)
C2—C3—H3B	109.00	O3—C16—N2	121.23 (15)
H3A—C3—H3B	108.00	O3—C16—C15	121.41 (15)
C4—C3—H3B	109.00	N2—C16—C15	117.30 (14)
C2—C3—H3A	109.00	O4—C17—N2	112.52 (12)
C4—C3—H3A	109.00	C13—C14—H14A	110.00
C5—C4—H4B	109.00	C13—C14—H14B	110.00
H4A—C4—H4B	108.00	C15—C14—H14A	110.00
C5—C4—H4A	109.00	C15—C14—H14B	110.00
C3—C4—H4A	109.00	H14A—C14—H14B	108.00
C3—C4—H4B	109.00	C14—C15—H15A	109.00
C4—C5—H5B	109.00	C14—C15—H15B	109.00
H5A—C5—H5B	108.00	C16—C15—H15A	109.00
C4—C5—H5A	109.00	C16—C15—H15B	109.00
C6—C5—H5B	109.00	H15A—C15—H15B	108.00
C6—C5—H5A	109.00	O4—C17—H17A	109.00
C1—C6—H6B	110.00	O4—C17—H17B	109.00
H6A—C6—H6B	108.00	N2—C17—H17A	109.00
C5—C6—H6B	110.00	N2—C17—H17B	109.00
C1—C6—H6A	110.00	H17A—C17—H17B	108.00

C7—N1—C1—C2	59.28 (18)	C4—C5—C6—C1	56.57 (17)
C7—N1—C1—C6	−177.90 (14)	N1—C7—C8—C9	−177.94 (14)
C1—N1—C7—C8	−176.66 (14)	C8—C7—C12—C10	54.9 (2)
C1—N1—C7—C12	60.53 (19)	C12—C7—C8—C9	−55.78 (19)
C16—N2—C17—O4	84.82 (17)	N1—C7—C12—C10	175.30 (14)
C17—N2—C16—O3	1.2 (2)	C7—C8—C9—C11	56.73 (18)
C17—N2—C16—C15	178.48 (13)	C8—C9—C11—C10	−57.9 (2)
N1—C1—C2—C3	176.74 (12)	C12—C10—C11—C9	57.7 (3)
C2—C1—C6—C5	−56.83 (17)	C11—C10—C12—C7	−55.9 (2)
C6—C1—C2—C3	56.21 (16)	O1—C13—C14—C15	−96.94 (16)
N1—C1—C6—C5	−179.81 (14)	O2—C13—C14—C15	82.16 (17)
C1—C2—C3—C4	−55.54 (17)	C13—C14—C15—C16	−166.86 (13)
C2—C3—C4—C5	55.81 (17)	C14—C15—C16—O3	95.92 (18)
C3—C4—C5—C6	−56.27 (17)	C14—C15—C16—N2	−81.33 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.892 (17)	2.597 (17)	3.285 (2)	134.7 (14)
N1—H1A···O2ⁱ	0.892 (17)	1.975 (17)	2.8546 (18)	168.7 (15)
N1—H1B···O1ⁱⁱ	0.95 (2)	1.80 (2)	2.740 (2)	174.3 (17)
N2—H2N···O2ⁱⁱⁱ	0.829 (17)	2.069 (17)	2.8914 (18)	171.1 (16)
O4—H4O···O3ⁱⁱⁱ	0.88 (2)	1.78 (2)	2.6423 (16)	166.4 (19)

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₂₄N⁺·C₅H₈NO₄⁻
M_r	328.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	5.6844 (5), 17.7967 (12), 18.4264 (16)
β (°)	95.495 (7)
V (Å³)	1855.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.45 × 0.13

Data collection
Diffractometer	Stoe IPDS2
Absorption correction	Multi-scan (MULscanABS in PLATON; Spek, 2009)
T_min, T_max	0.714, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11855, 3941, 2568
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.095, 0.93
No. of reflections	3941
No. of parameters	225
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16

Computer programs: X-AREA (Stoe & Cie, 2009), X-RED32 (Stoe & Cie, 2009), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.892 (17)	2.597 (17)	3.285 (2)	134.7 (14)
N1—H1A···O2ⁱ	0.892 (17)	1.975 (17)	2.8546 (18)	168.7 (15)
N1—H1B···O1ⁱⁱ	0.95 (2)	1.80 (2)	2.740 (2)	174.3 (17)
N2—H2N···O2ⁱⁱⁱ	0.829 (17)	2.069 (17)	2.8914 (18)	171.1 (16)
O4—H4O···O3ⁱⁱⁱ	0.88 (2)	1.78 (2)	2.6423 (16)	166.4 (19)

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x−1, y, z.

Acknowledgements

The authors gratefully acknowledge Dr Panchanatheeswaran for his support and many helpful discussions. HSE thanks the X-Ray Application LAB, CSEM, Neuchâtel, for access to the X-ray diffraction equipment.

References

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