4-Carbamoylpiperidinium 5-nitro­salicylate

Smith, G.; Wermuth, U.D.

doi:10.1107/S1600536810050129

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o122

https://doi.org/10.1107/S1600536810050129

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4-Carbamoylpiperidinium 5-nitrosalicylate

Graham Smith ^a ^* and Urs D. Wermuth ^a

^aFaculty of Science and Technology, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
^*Correspondence e-mail: g.smith@qut.edu.au

(Received 29 November 2010; accepted 30 November 2010; online 15 December 2010)

In the crystal structure of the title compound, C₆H₁₃N₂O⁺·C₇H₄NO₅⁻, the isonipecotamide cations and the 5-nitrosalicylate anions form hydrogen-bonded chain substructures through head-to-tail piperidinium–carboxylate N—H⋯O hydrogen bonds and through centrosymmetric cyclic head-to-head amide–amide hydrogen-bonding associations [graph set R₂²(8)]. These chains are cross-linked by amide–carboxylate N—H⋯O and piperidinium–nitro N—H⋯O associations, giving a sheet structure.

Related literature

For structural data on isonipecotamide salts, see: Smith et al. (2010 ); Smith & Wermuth (2010a ,b ,c ,d ). For structures of 5-nitrosalicylates, see: Smith et al. (2005 ). For hydrogen-bonding graph-set and motif classification, see: Etter et al. (1990 ); Allen et al. (1998 ).

Experimental

Crystal data

C₆H₁₃N₂O⁺·C₇H₄NO₅⁻
M_r = 311.30
Monoclinic, P 2₁ /n
a = 15.0442 (10) Å
b = 5.5851 (3) Å
c = 17.1939 (10) Å
β = 91.466 (6)°
V = 1444.22 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 200 K
0.40 × 0.25 × 0.16 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.912, T_max = 0.980
9191 measured reflections
2833 independent reflections
1850 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.092
S = 0.95
2833 reflections
219 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H11A⋯O12ⁱ	1.00 (2)	1.71 (2)	2.688 (2)	164.2 (18)
N1A—H12A⋯O11	0.95 (2)	1.80 (2)	2.747 (2)	173.9 (17)
N41A—H41A⋯O52ⁱⁱ	0.83 (2)	2.39 (2)	3.216 (2)	170.8 (19)
N41A—H42A⋯O41Aⁱⁱⁱ	0.99 (2)	1.91 (2)	2.873 (2)	164.8 (18)
O2—H2⋯O12	0.96 (2)	1.58 (2)	2.4897 (18)	156 (2)
Symmetry codes: (i) x, y+1, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ) within WinGX (Farrugia, 1999 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810050129/bt5426sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050129/bt5426Isup2.hkl

checkCIF report

Comment top

The structures of a number of salts of the amide piperidine-4-carboxamide (isonipecotamide, INIPA) with a range of carboxylic acids, mainly aromatic, are now known (Smith & Wermuth, 2010a, 2010b, 2010c, Smith & Wermuth, 2010d,; Smith et al., 2010). The title compound C₆H₁₃N₂O⁺ C₇H₄NO₅^- (I) was obtained from the 1:1 stoichiometric reaction of 5-nitrosalicylic acid with INIPA in methanol and the structure is reported here.

In (I) (Fig. 1) the cations and anions form hydrogn-bonded chain substructures through head-to-tail piperidinium N—H···O_carboxyl hydrogen bonds and through centrosymmetric cyclic head-to-head amide–amide hydrogen-bonding associations [graph set R²₂(8) (Etter et al., 1990)]. These chains are cross linked by amide N—H···O_carboxyl and piperidinium N—H···O_nitro associations to giving a two-dimensional sheet structure (Fig. 2). The amide-amide dimer association [the 'amide motif' (Allen et al., 1998)] is relatively common among the INIPA salts (Smith & Wermuth, 2010b; Smith et al., 2010).

The 5-nitrosalicylate anions are essentially planar [torsion angles for the carboxyl group (C2–C1–C11–O11), 178.30 (16)° and the nitro group (C4–C5–N5–O52), -175.57 (16)°], which is the usual conformation for this anion in its proton-transfer compounds (Smith et al., 2005).

Related literature top

For structural data on isonipecotamide salts, see: Smith et al. (2010); Smith & Wermuth (2010a,b,c,d). For structures of 5-nitrosalicylates, see: Smith et al. (2005). For hydrogen-bonding graph-set and motif classification, see: Etter et al. (1990); Allen et al. (1998).

Experimental top

The title compound was synthesized by heating together under reflux for 10 minutes, 1 mmol quantities of piperidine-4-carboxamide (isonipecotamide) and 5-nitrosalicylic acid in 50 ml of methanol. After concentration to ca 30 ml, partial room temperature evaporation of the hot-filtered solution gave pale yellow prisms of the title compound from which a specimen was cleaved for the X-ray analysis.

Structure description top

For structural data on isonipecotamide salts, see: Smith et al. (2010); Smith & Wermuth (2010a,b,c,d). For structures of 5-nitrosalicylates, see: Smith et al. (2005). For hydrogen-bonding graph-set and motif classification, see: Etter et al. (1990); Allen et al. (1998).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular configuration and atom naming scheme for the INIPA cation and the 5-nitrosalicylate anion in (I). The inter-species hydrogen bond is shown as a dashed line and displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. The hydrogen-bonded chain substructures in (I) showing the cyclic R²₂(8) amide–amide and cation–anion associations. Non-associative H atoms are omitted and hydrogen bonds are shown as dashed lines. For symmetry codes, see Table 1.

4-carbamoylpiperidine 2-hydroxy-5-nitrobenzoate top

Crystal data top

C₆H₁₃N₂O⁺·C₇H₄NO₅⁻	F(000) = 656
M_r = 311.30	D_x = 1.432 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 463 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 15.0442 (10) Å	Cell parameters from 3270 reflections
b = 5.5851 (3) Å	θ = 3.6–28.7°
c = 17.1939 (10) Å	µ = 0.12 mm⁻¹
β = 91.466 (6)°	T = 200 K
V = 1444.22 (15) Å³	Prism, pale yellow
Z = 4	0.40 × 0.25 × 0.16 mm

Data collection top

Oxford Diffraction Gemini-S CCD-detector diffractometer	2833 independent reflections
Radiation source: Enhance (Mo)X-ray source	1850 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 16.077 pixels mm^-1	θ_max = 26.0°, θ_min = 3.6°
ω scans	h = −18→18
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −6→6
T_min = 0.912, T_max = 0.980	l = −12→21
9191 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0486P)²] where P = (F_o² + 2F_c²)/3
2833 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.11 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₆H₁₃N₂O⁺·C₇H₄NO₅⁻	V = 1444.22 (15) Å³
M_r = 311.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.0442 (10) Å	µ = 0.12 mm⁻¹
b = 5.5851 (3) Å	T = 200 K
c = 17.1939 (10) Å	0.40 × 0.25 × 0.16 mm
β = 91.466 (6)°

Data collection top

Oxford Diffraction Gemini-S CCD-detector diffractometer	2833 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	1850 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.980	R_int = 0.031
9191 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.11 e Å⁻³
2833 reflections	Δρ_min = −0.17 e Å⁻³
219 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. 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
O41A	0.44900 (9)	0.0250 (2)	0.90133 (7)	0.0575 (5)
N1A	0.39663 (10)	0.5656 (3)	0.69549 (9)	0.0452 (6)
N41A	0.54984 (11)	0.2658 (4)	0.96084 (10)	0.0480 (6)
C2A	0.49383 (12)	0.5253 (3)	0.70538 (12)	0.0545 (7)
C3A	0.51390 (12)	0.3391 (3)	0.76686 (10)	0.0516 (7)
C4A	0.47324 (11)	0.4101 (3)	0.84420 (9)	0.0423 (6)
C5A	0.37359 (11)	0.4529 (3)	0.83207 (10)	0.0451 (6)
C6A	0.35478 (11)	0.6369 (3)	0.76956 (10)	0.0463 (6)
C41A	0.48930 (12)	0.2177 (3)	0.90488 (10)	0.0435 (6)
O2	0.40541 (10)	−0.1530 (2)	0.42604 (8)	0.0605 (5)
O11	0.32739 (8)	0.1529 (2)	0.63160 (7)	0.0507 (4)
O12	0.39253 (9)	−0.1469 (3)	0.57010 (7)	0.0600 (5)
O51	0.16400 (10)	0.7176 (3)	0.34253 (8)	0.0729 (6)
O52	0.17024 (9)	0.7584 (2)	0.46713 (8)	0.0562 (5)
N5	0.19077 (10)	0.6528 (3)	0.40756 (9)	0.0510 (6)
C1	0.32654 (11)	0.1565 (3)	0.49283 (9)	0.0388 (6)
C2	0.35489 (12)	0.0445 (3)	0.42422 (10)	0.0460 (6)
C3	0.32936 (13)	0.1368 (4)	0.35198 (10)	0.0550 (7)
C4	0.27649 (13)	0.3354 (4)	0.34625 (10)	0.0529 (7)
C5	0.24816 (11)	0.4452 (3)	0.41392 (9)	0.0423 (6)
C6	0.27300 (11)	0.3580 (3)	0.48665 (9)	0.0396 (6)
C11	0.35061 (12)	0.0510 (3)	0.57113 (10)	0.0443 (6)
H4A	0.50110	0.55900	0.86250	0.0510*
H11A	0.3874 (12)	0.689 (4)	0.6540 (12)	0.065 (6)*
H12A	0.3699 (12)	0.422 (4)	0.6763 (11)	0.063 (6)*
H21A	0.52260	0.67460	0.72000	0.0650*
H22A	0.51770	0.47330	0.65630	0.0650*
H31A	0.57780	0.32230	0.77390	0.0620*
H32A	0.49000	0.18580	0.75010	0.0620*
H41A	0.5753 (13)	0.398 (4)	0.9620 (11)	0.054 (7)*
H42A	0.5568 (13)	0.147 (4)	1.0029 (12)	0.075 (7)*
H51A	0.34480	0.30340	0.81770	0.0540*
H52A	0.34870	0.50710	0.88050	0.0540*
H61A	0.29100	0.65250	0.76110	0.0560*
H62A	0.37790	0.79110	0.78630	0.0560*
H2	0.4119 (15)	−0.184 (4)	0.4809 (14)	0.109 (9)*
H3	0.34850	0.06260	0.30700	0.0660*
H4	0.25970	0.39640	0.29770	0.0630*
H6	0.25380	0.43450	0.53130	0.0470*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O41A	0.0736 (9)	0.0473 (8)	0.0500 (8)	0.0056 (7)	−0.0280 (7)	−0.0127 (6)
N1A	0.0518 (10)	0.0467 (10)	0.0368 (9)	−0.0015 (8)	−0.0070 (7)	−0.0078 (8)
N41A	0.0472 (10)	0.0463 (10)	0.0495 (10)	0.0124 (9)	−0.0208 (8)	−0.0123 (9)
C2A	0.0482 (12)	0.0624 (13)	0.0531 (12)	0.0009 (10)	0.0056 (9)	−0.0120 (10)
C3A	0.0439 (11)	0.0576 (12)	0.0530 (12)	0.0122 (9)	−0.0014 (9)	−0.0134 (10)
C4A	0.0421 (10)	0.0420 (10)	0.0420 (10)	0.0090 (8)	−0.0125 (8)	−0.0149 (8)
C5A	0.0422 (10)	0.0580 (11)	0.0348 (10)	0.0155 (9)	−0.0066 (8)	−0.0066 (9)
C6A	0.0429 (10)	0.0561 (11)	0.0396 (10)	0.0127 (9)	−0.0066 (8)	−0.0080 (9)
C41A	0.0418 (10)	0.0454 (11)	0.0426 (10)	0.0189 (9)	−0.0139 (8)	−0.0195 (9)
O2	0.0834 (10)	0.0489 (8)	0.0501 (8)	−0.0077 (8)	0.0216 (8)	−0.0104 (7)
O11	0.0597 (8)	0.0621 (8)	0.0303 (7)	−0.0163 (7)	−0.0002 (6)	−0.0097 (6)
O12	0.0762 (10)	0.0563 (8)	0.0474 (8)	0.0017 (8)	0.0024 (7)	−0.0007 (7)
O51	0.0929 (11)	0.0800 (11)	0.0455 (8)	−0.0009 (8)	−0.0025 (8)	0.0174 (7)
O52	0.0630 (9)	0.0544 (8)	0.0516 (9)	−0.0081 (7)	0.0075 (7)	−0.0025 (7)
N5	0.0580 (10)	0.0546 (10)	0.0406 (10)	−0.0209 (9)	0.0067 (8)	0.0033 (8)
C1	0.0423 (10)	0.0414 (10)	0.0331 (10)	−0.0211 (9)	0.0064 (7)	−0.0067 (8)
C2	0.0590 (12)	0.0407 (10)	0.0390 (11)	−0.0221 (9)	0.0148 (9)	−0.0066 (9)
C3	0.0810 (15)	0.0528 (12)	0.0322 (11)	−0.0223 (11)	0.0224 (10)	−0.0069 (9)
C4	0.0715 (14)	0.0585 (12)	0.0291 (10)	−0.0264 (11)	0.0099 (9)	0.0020 (9)
C5	0.0483 (11)	0.0438 (11)	0.0352 (10)	−0.0184 (9)	0.0073 (8)	0.0017 (8)
C6	0.0430 (10)	0.0457 (10)	0.0302 (9)	−0.0230 (9)	0.0056 (7)	−0.0079 (8)
C11	0.0453 (11)	0.0505 (11)	0.0369 (11)	−0.0208 (9)	0.0001 (8)	−0.0070 (9)

Geometric parameters (Å, º) top

O41A—C41A	1.236 (2)	C2A—H22A	0.9700
O2—C2	1.340 (2)	C2A—H21A	0.9700
O11—C11	1.243 (2)	C3A—H31A	0.9700
O12—C11	1.273 (2)	C3A—H32A	0.9700
O51—N5	1.233 (2)	C4A—H4A	0.9800
O52—N5	1.228 (2)	C5A—H51A	0.9700
O2—H2	0.96 (2)	C5A—H52A	0.9700
N1A—C6A	1.489 (2)	C6A—H62A	0.9700
N1A—C2A	1.485 (2)	C6A—H61A	0.9700
N41A—C41A	1.335 (2)	C1—C6	1.386 (2)
N1A—H12A	0.95 (2)	C1—C11	1.505 (2)
N1A—H11A	1.00 (2)	C1—C2	1.411 (2)
N41A—H41A	0.83 (2)	C2—C3	1.390 (3)
N41A—H42A	0.99 (2)	C3—C4	1.367 (3)
N5—C5	1.448 (2)	C4—C5	1.392 (2)
C2A—C3A	1.508 (3)	C5—C6	1.385 (2)
C3A—C4A	1.530 (2)	C3—H3	0.9300
C4A—C5A	1.527 (2)	C4—H4	0.9300
C4A—C41A	1.513 (2)	C6—H6	0.9300
C5A—C6A	1.509 (2)

C2—O2—H2	102.4 (13)	C5A—C4A—H4A	109.00
C2A—N1A—C6A	112.29 (14)	C3A—C4A—H4A	109.00
C2A—N1A—H12A	108.5 (12)	C4A—C5A—H52A	109.00
C6A—N1A—H11A	111.8 (12)	C6A—C5A—H51A	109.00
H11A—N1A—H12A	106.5 (17)	C4A—C5A—H51A	109.00
C6A—N1A—H12A	109.7 (11)	C6A—C5A—H52A	109.00
C2A—N1A—H11A	107.8 (11)	H51A—C5A—H52A	108.00
H41A—N41A—H42A	122.7 (18)	H61A—C6A—H62A	108.00
C41A—N41A—H42A	116.8 (12)	C5A—C6A—H61A	110.00
C41A—N41A—H41A	120.1 (13)	C5A—C6A—H62A	110.00
O51—N5—O52	122.14 (16)	N1A—C6A—H61A	109.00
O51—N5—C5	118.93 (15)	N1A—C6A—H62A	110.00
O52—N5—C5	118.93 (14)	C2—C1—C11	120.22 (15)
N1A—C2A—C3A	111.33 (15)	C6—C1—C11	120.82 (14)
C2A—C3A—C4A	110.68 (14)	C2—C1—C6	118.90 (15)
C3A—C4A—C41A	110.79 (14)	O2—C2—C1	121.94 (15)
C5A—C4A—C41A	110.14 (14)	O2—C2—C3	118.03 (16)
C3A—C4A—C5A	109.56 (13)	C1—C2—C3	120.02 (16)
C4A—C5A—C6A	111.69 (14)	C2—C3—C4	120.82 (17)
N1A—C6A—C5A	110.57 (14)	C3—C4—C5	119.17 (16)
O41A—C41A—N41A	122.38 (17)	N5—C5—C6	119.77 (14)
N41A—C41A—C4A	116.62 (16)	C4—C5—C6	121.25 (16)
O41A—C41A—C4A	120.99 (15)	N5—C5—C4	118.98 (15)
N1A—C2A—H21A	109.00	C1—C6—C5	119.84 (15)
N1A—C2A—H22A	109.00	O11—C11—C1	120.16 (15)
C3A—C2A—H21A	109.00	O12—C11—C1	115.81 (15)
C3A—C2A—H22A	109.00	O11—C11—O12	123.99 (16)
H21A—C2A—H22A	108.00	C2—C3—H3	120.00
C2A—C3A—H32A	110.00	C4—C3—H3	120.00
C4A—C3A—H31A	109.00	C3—C4—H4	120.00
C2A—C3A—H31A	110.00	C5—C4—H4	120.00
C4A—C3A—H32A	109.00	C1—C6—H6	120.00
H31A—C3A—H32A	108.00	C5—C6—H6	120.00
C41A—C4A—H4A	109.00

C6A—N1A—C2A—C3A	56.83 (19)	C6—C1—C2—C3	0.2 (3)
C2A—N1A—C6A—C5A	−56.01 (18)	C11—C1—C2—O2	−1.8 (3)
O51—N5—C5—C4	4.5 (2)	C11—C1—C2—C3	177.28 (17)
O51—N5—C5—C6	−174.74 (16)	C2—C1—C6—C5	0.2 (2)
O52—N5—C5—C4	−175.57 (16)	C11—C1—C6—C5	−176.88 (16)
O52—N5—C5—C6	5.2 (2)	C2—C1—C11—O11	178.30 (16)
N1A—C2A—C3A—C4A	−56.37 (19)	C2—C1—C11—O12	−3.8 (2)
C2A—C3A—C4A—C5A	55.43 (18)	C6—C1—C11—O11	−4.7 (3)
C2A—C3A—C4A—C41A	177.15 (14)	C6—C1—C11—O12	173.26 (16)
C5A—C4A—C41A—O41A	49.2 (2)	O2—C2—C3—C4	178.81 (18)
C5A—C4A—C41A—N41A	−132.02 (17)	C1—C2—C3—C4	−0.3 (3)
C3A—C4A—C41A—O41A	−72.2 (2)	C2—C3—C4—C5	0.0 (3)
C3A—C4A—C5A—C6A	−55.62 (18)	C3—C4—C5—N5	−178.83 (17)
C41A—C4A—C5A—C6A	−177.72 (14)	C3—C4—C5—C6	0.4 (3)
C3A—C4A—C41A—N41A	106.61 (18)	N5—C5—C6—C1	178.76 (15)
C4A—C5A—C6A—N1A	55.72 (18)	C4—C5—C6—C1	−0.5 (3)
C6—C1—C2—O2	−178.84 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H11A···O12ⁱ	1.00 (2)	1.71 (2)	2.688 (2)	164.2 (18)
N1A—H12A···O11	0.95 (2)	1.80 (2)	2.747 (2)	173.9 (17)
N41A—H41A···O52ⁱⁱ	0.83 (2)	2.39 (2)	3.216 (2)	170.8 (19)
N41A—H42A···O41Aⁱⁱⁱ	0.99 (2)	1.91 (2)	2.873 (2)	164.8 (18)
O2—H2···O12	0.96 (2)	1.58 (2)	2.4897 (18)	156 (2)
C2A—H22A···O2^iv	0.97	2.57	3.450 (2)	150
C6A—H61A···O11^v	0.97	2.60	3.263 (2)	126
C6A—H62A···O41Aⁱ	0.97	2.58	3.417 (2)	145

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

Experimental details

Crystal data
Chemical formula	C₆H₁₃N₂O⁺·C₇H₄NO₅⁻
M_r	311.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	200
a, b, c (Å)	15.0442 (10), 5.5851 (3), 17.1939 (10)
β (°)	91.466 (6)
V (Å³)	1444.22 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.40 × 0.25 × 0.16

Data collection
Diffractometer	Oxford Diffraction Gemini-S CCD-detector
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.912, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	9191, 2833, 1850
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.092, 0.95
No. of reflections	2833
No. of parameters	219
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.17

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H11A···O12ⁱ	1.00 (2)	1.71 (2)	2.688 (2)	164.2 (18)
N1A—H12A···O11	0.95 (2)	1.80 (2)	2.747 (2)	173.9 (17)
N41A—H41A···O52ⁱⁱ	0.83 (2)	2.39 (2)	3.216 (2)	170.8 (19)
N41A—H42A···O41Aⁱⁱⁱ	0.99 (2)	1.91 (2)	2.873 (2)	164.8 (18)
O2—H2···O12	0.96 (2)	1.58 (2)	2.4897 (18)	156 (2)

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

Acknowledgements

The authors acknowledge financial support from the Australian Research Council, the Faculty of Science and Technology and the University Library, Queensland University of Technology, and the School of Biomolecular and Physical Sciences, Griffith University.

References

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