4-(2-Hydroxy­ethyl)anilinium 3,5-dinitro­benzoate

Smith, G.; Wermuth, U.D.

doi:10.1107/S1600536809030426

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2109

doi:10.1107/S1600536809030426

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4-(2-Hydroxyethyl)anilinium 3,5-dinitrobenzoate

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

^aSchool of Physical and Chemical Sciences, Queensland University of Technology, GPO Box 2434, Brisbane, Qld 4001, Australia
^*Correspondence e-mail: g.smith@qut.edu.au

(Received 16 July 2009; accepted 31 July 2009; online 8 August 2009)

In the title compound, C₈H₁₂NO⁺·C₇H₃N₂O₆⁻, the anilinium and hydroxyl protons of the cation result in N—H⋯O, N—H⋯(O,O) and O—H⋯O hydrogen-bonding interactions with carboxylate O-atom acceptors, forming a two-dimensional network structure. An intermolecular C—H⋯O interaction is also present.

Related literature

For related structures, see: Etter & Frankenbach (1989 ); Lynch et al. (1991a ,b , 1992 , 1993 ); Ranganathan & Pedireddi (1998 ); Aakeröy et al. (2003 ); Hosomi et al. (2000 ).

Experimental

Crystal data

C₈H₁₂NO⁺·C₇H₃N₂O₆⁻
M_r = 349.30
Monoclinic, P 2₁ /n
a = 15.9566 (19) Å
b = 5.7844 (5) Å
c = 17.4118 (14) Å
β = 102.811 (10)°
V = 1567.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 297 K
0.30 × 0.30 × 0.25 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.950, T_max = 0.980
5928 measured reflections
3061 independent reflections
2203 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.099
S = 0.98
3061 reflections
242 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 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
O11A—H11A⋯O11ⁱ	0.89 (2)	1.88 (2)	2.7569 (16)	168 (2)
N4A—H41A⋯O12	0.958 (19)	1.924 (19)	2.845 (2)	160.8 (17)
N4A—H42A⋯O11ⁱⁱ	0.936 (19)	2.02 (2)	2.8905 (19)	154.0 (18)
N4A—H42A⋯O12ⁱⁱ	0.936 (19)	2.53 (2)	3.1033 (18)	119.9 (14)
N4A—H43A⋯O11Aⁱⁱⁱ	1.005 (19)	1.783 (19)	2.785 (2)	174.4 (19)
C5A—H5A⋯O11A^iv	0.93	2.43	3.317 (2)	161
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030426/bt5012sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809030426/bt5012Isup2.hkl

checkCIF report

Comment top

The nitro-substituted aromatic acid, 3,5-dinitrobenzoic acid (3,5-DNBA) has been used to synthesize chiral crystalline adduct materials with physical properties potentially useful in applications such as nonlinear optics, giving e.g. the compound 3,5-DNBA–4-aminobenzoic acid (1/1) (Etter & Frankenbach, 1989). Since that time there have been a large number of 3,5-DNBA adduct structures reported, e.g. with indole-3-acetic acid (1:1) (Lynch et al., 1991a), phenoxyacetic acid (a 2:1 monohydrate) (Lynch et al., 1991b), 1,4-diiodobenzene (2:1) (Ranganathan & Pedireddi (1998)], a series of alkyl-substituted carbazoles (all 1:1) (Hosomi et al., 2000) and benzamide (1:1)] (Aakeröy et al., 2003); Proton-transfer compounds and proton-transfer-3,5-DNBA adduct compounds are also very common, e.g. with the herbicides amitrole (3-amino-1,2,4-triazole) and prometryn (N,N'-bis(1-methylethyl)-6- methylthio-1,2,4-triazine-2,4-diamide) (Lynch et al., 1993) (all 1:1)

In the light of this background we looked at 3,5-DNBA as a possible means of obtaining a crystalline compound from the non-crystalline aromatic Lewis base 2-(4-aminophenyl)ethanol. The 1:1 stoichiometric reaction of 3,5-DNBA with this reagent in 50% ethanol–water was expected to give either an anilinium salt or an adduct salt and the result was a 1:1 salt 4-(2-hydroxyethyl)anilinium 3,5-dinitrobenzoate C₈H₁₂NO⁺. C₇H₃N₂O₆^- (I), the structure of which is reported here.

With (I) (Fig. 1), proton transfer occurs and the resulting anilinium group is subsequently involved in four hydrogen-bonding interactions with only carboxylate-O acceptors (Table 1). One of these associations is asymmetric cyclic [N–H···O,O', graph set R²₁(4)]. These interactions, together with an hydroxyl O–H···O_carboxyl hydrogen bond give a two-dimensional network structure which lies in the (a0c) plane and extends down the b cell direction (Fig. 2). Also present in the structure are short inversion-related intermolecular nitro O···O nonbonding interactions [O32···O32^iv, 2.8799 (18) Å; symmetry code: (iv) -x + 1, -y, -z]. The 3,5-DNBA anion is essentially planar [C2–C1–C11–O11A, -172.71 (13)° (carboxyl); C2–C3–N3–O32, -161.49 (14)° and C4–C5–N5–O52, -177.25 (13)° (nitro)].

Related literature top

For related structures, see: Etter & Frankenbach (1989); Lynch et al. (1991a,b, 1992, 1993); Ranganathan & Pedireddi (1998); Aakeröy et al. (2003); Hosomi et al. (2000).

Experimental top

The title compound was synthesized by heating together 1 mmol quantities of 2-(4-aminophenyl)ethanol with 3,5-dinitrobenzoic acid in 50 ml of 50% ethanol–water under reflux for 10 minutes. After concentration to ca 30 ml, partial room temperature evaporation of the hot-filtered solution gave light brown coloured flat prisms (m.p. 389 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); 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 substituted anilinium cation and the 3,5-dinitrobenzoate anion in (I). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The two-dimensional hydrogen-bonded network structure of (I) extending across the (a0c) plane and viewed down the approximate b axial direction of the unit cell, showing hydrogen-bonding associations as dashed lines. Non-interactive H atoms are omitted. For symmetry codes, see Table 1.

4-(2-Hydroxyethyl)anilinium 3,5-dinitrobenzoate top

Crystal data top

C₈H₁₂NO⁺·C₇H₃N₂O₆⁻	F(000) = 728
M_r = 349.30	D_x = 1.480 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 389 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 15.9566 (19) Å	Cell parameters from 3103 reflections
b = 5.7844 (5) Å	θ = 3.0–28.9°
c = 17.4118 (14) Å	µ = 0.12 mm⁻¹
β = 102.811 (10)°	T = 297 K
V = 1567.1 (3) Å³	Cut block, pale brown
Z = 4	0.30 × 0.30 × 0.25 mm

Data collection top

Oxford Diffraction Gemini-S CCD-detector diffractometer	3061 independent reflections
Radiation source: Enhance (Mo) X-ray source	2203 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω scans	θ_max = 26.0°, θ_min = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
T_min = 0.950, T_max = 0.980	k = −4→7
5928 measured reflections	l = −21→15

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0603P)²] where P = (F_o² + 2F_c²)/3
3061 reflections	(Δ/σ)_max < 0.001
242 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₈H₁₂NO⁺·C₇H₃N₂O₆⁻	V = 1567.1 (3) Å³
M_r = 349.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.9566 (19) Å	µ = 0.12 mm⁻¹
b = 5.7844 (5) Å	T = 297 K
c = 17.4118 (14) Å	0.30 × 0.30 × 0.25 mm
β = 102.811 (10)°

Data collection top

Oxford Diffraction Gemini-S CCD-detector diffractometer	3061 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2203 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.980	R_int = 0.017
5928 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.21 e Å⁻³
3061 reflections	Δρ_min = −0.17 e Å⁻³
242 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
O11A	0.46281 (7)	0.8636 (2)	0.32392 (7)	0.0479 (4)
N4A	0.09143 (8)	0.6731 (3)	0.07459 (9)	0.0423 (4)
C1A	0.33713 (9)	0.9649 (3)	0.17095 (8)	0.0376 (5)
C2A	0.32916 (10)	0.7560 (3)	0.13049 (10)	0.0468 (5)
C3A	0.24921 (10)	0.6600 (3)	0.09931 (10)	0.0458 (5)
C4A	0.17646 (9)	0.7749 (2)	0.10760 (8)	0.0343 (4)
C5A	0.18206 (9)	0.9815 (3)	0.14700 (9)	0.0423 (5)
C6A	0.26212 (10)	1.0747 (3)	0.17881 (10)	0.0435 (5)
C21A	0.49028 (10)	0.9216 (3)	0.25331 (10)	0.0541 (6)
C31A	0.42384 (9)	1.0756 (3)	0.20306 (10)	0.0493 (5)
O11	0.04161 (6)	−0.00501 (19)	−0.08313 (7)	0.0524 (4)
O12	0.10800 (7)	0.31952 (19)	−0.03468 (7)	0.0518 (4)
O31	0.42127 (8)	0.3454 (2)	0.01994 (9)	0.0690 (5)
O32	0.48427 (7)	0.1694 (2)	−0.06214 (8)	0.0596 (4)
O51	0.34790 (7)	−0.5258 (2)	−0.18874 (7)	0.0600 (4)
O52	0.21061 (8)	−0.5622 (2)	−0.20625 (7)	0.0544 (4)
N3	0.42210 (8)	0.2056 (2)	−0.03294 (8)	0.0456 (5)
N5	0.27785 (8)	−0.4606 (2)	−0.17929 (7)	0.0410 (4)
C1	0.19176 (8)	0.0264 (2)	−0.07694 (8)	0.0335 (4)
C2	0.26684 (9)	0.1488 (2)	−0.04825 (8)	0.0359 (5)
C3	0.34373 (9)	0.0683 (3)	−0.06244 (9)	0.0356 (4)
C4	0.34961 (9)	−0.1305 (2)	−0.10445 (9)	0.0369 (4)
C5	0.27433 (9)	−0.2501 (2)	−0.13187 (8)	0.0344 (4)
C6	0.19600 (9)	−0.1775 (2)	−0.11857 (8)	0.0349 (4)
C11	0.10697 (9)	0.1224 (3)	−0.06366 (9)	0.0376 (5)
H2A	0.37840	0.67910	0.12420	0.0560*
H3A	0.24490	0.51900	0.07300	0.0550*
H5A	0.13250	1.05830	0.15230	0.0510*
H6A	0.26570	1.21390	0.20610	0.0520*
H11A	0.4946 (13)	0.751 (4)	0.3511 (12)	0.077 (7)*
H21A	0.49730	0.78200	0.22460	0.0650*
H22A	0.54520	1.00100	0.26650	0.0650*
H31A	0.44640	1.13040	0.15900	0.0590*
H32A	0.41540	1.20950	0.23400	0.0590*
H41A	0.0919 (12)	0.580 (3)	0.0292 (12)	0.069 (6)*
H42A	0.0494 (13)	0.788 (3)	0.0611 (12)	0.069 (6)*
H43A	0.0745 (12)	0.566 (3)	0.1140 (12)	0.074 (6)*
H2	0.26560	0.28400	−0.01970	0.0430*
H4	0.40170	−0.18130	−0.11380	0.0440*
H6	0.14660	−0.26430	−0.13730	0.0420*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O11A	0.0444 (6)	0.0510 (7)	0.0489 (7)	0.0053 (5)	0.0116 (5)	0.0101 (6)
N4A	0.0347 (7)	0.0486 (8)	0.0425 (8)	−0.0028 (6)	0.0065 (6)	−0.0058 (7)
C1A	0.0356 (8)	0.0449 (9)	0.0319 (8)	−0.0004 (7)	0.0067 (6)	0.0067 (7)
C2A	0.0335 (8)	0.0548 (10)	0.0541 (10)	0.0072 (7)	0.0141 (7)	−0.0055 (8)
C3A	0.0456 (9)	0.0435 (9)	0.0501 (10)	0.0029 (7)	0.0146 (8)	−0.0114 (8)
C4A	0.0328 (7)	0.0388 (8)	0.0308 (7)	−0.0001 (6)	0.0063 (6)	0.0004 (7)
C5A	0.0322 (8)	0.0431 (9)	0.0501 (10)	0.0093 (7)	0.0058 (7)	−0.0048 (8)
C6A	0.0443 (9)	0.0371 (8)	0.0469 (9)	0.0024 (7)	0.0057 (7)	−0.0059 (7)
C21A	0.0331 (8)	0.0813 (12)	0.0484 (10)	−0.0022 (8)	0.0100 (7)	0.0085 (9)
C31A	0.0380 (8)	0.0643 (11)	0.0455 (9)	−0.0075 (8)	0.0092 (7)	0.0108 (8)
O11	0.0340 (6)	0.0542 (7)	0.0722 (8)	−0.0052 (5)	0.0186 (6)	−0.0177 (6)
O12	0.0423 (6)	0.0502 (7)	0.0635 (8)	0.0051 (5)	0.0130 (5)	−0.0216 (6)
O31	0.0583 (8)	0.0695 (9)	0.0818 (10)	−0.0207 (6)	0.0211 (7)	−0.0324 (8)
O32	0.0366 (6)	0.0669 (8)	0.0808 (9)	−0.0044 (5)	0.0251 (6)	−0.0015 (7)
O51	0.0541 (7)	0.0592 (8)	0.0694 (8)	0.0179 (6)	0.0193 (6)	−0.0151 (6)
O52	0.0585 (7)	0.0490 (7)	0.0551 (8)	−0.0050 (6)	0.0111 (6)	−0.0155 (6)
N3	0.0385 (7)	0.0448 (8)	0.0540 (9)	−0.0055 (6)	0.0113 (6)	−0.0019 (7)
N5	0.0487 (8)	0.0381 (7)	0.0366 (7)	0.0082 (6)	0.0102 (6)	−0.0009 (6)
C1	0.0334 (7)	0.0366 (8)	0.0320 (7)	0.0018 (6)	0.0105 (6)	0.0014 (6)
C2	0.0399 (8)	0.0343 (8)	0.0353 (8)	0.0011 (6)	0.0124 (6)	−0.0031 (6)
C3	0.0325 (7)	0.0389 (8)	0.0361 (8)	−0.0015 (6)	0.0093 (6)	0.0010 (7)
C4	0.0341 (7)	0.0410 (8)	0.0381 (8)	0.0058 (6)	0.0136 (6)	0.0029 (7)
C5	0.0413 (8)	0.0335 (7)	0.0294 (7)	0.0056 (6)	0.0098 (6)	0.0004 (6)
C6	0.0338 (7)	0.0362 (8)	0.0343 (8)	−0.0013 (6)	0.0069 (6)	−0.0019 (7)
C11	0.0349 (8)	0.0430 (9)	0.0356 (8)	0.0020 (7)	0.0096 (6)	−0.0029 (7)

Geometric parameters (Å, º) top

O11A—C21A	1.434 (2)	C5A—C6A	1.384 (2)
O11A—H11A	0.89 (2)	C21A—C31A	1.507 (2)
O11—C11	1.2606 (19)	C2A—H2A	0.9300
O12—C11	1.246 (2)	C3A—H3A	0.9300
O31—N3	1.2277 (19)	C5A—H5A	0.9300
O32—N3	1.2289 (18)	C6A—H6A	0.9300
O51—N5	1.2249 (17)	C21A—H21A	0.9700
O52—N5	1.2221 (18)	C21A—H22A	0.9700
N4A—C4A	1.474 (2)	C31A—H31A	0.9700
N4A—H43A	1.005 (19)	C31A—H32A	0.9700
N4A—H41A	0.958 (19)	C1—C2	1.3859 (19)
N4A—H42A	0.936 (19)	C1—C6	1.3939 (17)
N3—C3	1.474 (2)	C1—C11	1.527 (2)
N5—C5	1.4792 (17)	C2—C3	1.385 (2)
C1A—C6A	1.388 (2)	C3—C4	1.377 (2)
C1A—C2A	1.390 (2)	C4—C5	1.377 (2)
C1A—C31A	1.515 (2)	C5—C6	1.386 (2)
C2A—C3A	1.387 (2)	C2—H2	0.9300
C3A—C4A	1.373 (2)	C4—H4	0.9300
C4A—C5A	1.371 (2)	C6—H6	0.9300

C21A—O11A—H11A	112.3 (13)	C1A—C6A—H6A	119.00
C4A—N4A—H43A	110.1 (11)	C31A—C21A—H21A	110.00
H41A—N4A—H42A	109.2 (17)	O11A—C21A—H22A	110.00
H42A—N4A—H43A	108.8 (17)	O11A—C21A—H21A	110.00
C4A—N4A—H42A	111.1 (12)	C31A—C21A—H22A	110.00
H41A—N4A—H43A	105.6 (15)	H21A—C21A—H22A	108.00
C4A—N4A—H41A	111.8 (12)	H31A—C31A—H32A	107.00
O31—N3—O32	124.50 (14)	C1A—C31A—H31A	108.00
O32—N3—C3	117.66 (13)	C1A—C31A—H32A	108.00
O31—N3—C3	117.82 (13)	C21A—C31A—H31A	108.00
O51—N5—O52	123.36 (13)	C21A—C31A—H32A	108.00
O52—N5—C5	118.13 (12)	C2—C1—C6	118.82 (12)
O51—N5—C5	118.50 (12)	C2—C1—C11	118.94 (12)
C2A—C1A—C6A	117.62 (14)	C6—C1—C11	122.23 (12)
C6A—C1A—C31A	120.48 (15)	C1—C2—C3	119.55 (12)
C2A—C1A—C31A	121.87 (14)	N3—C3—C2	118.25 (14)
C1A—C2A—C3A	121.28 (15)	N3—C3—C4	118.85 (13)
C2A—C3A—C4A	119.40 (15)	C2—C3—C4	122.88 (14)
N4A—C4A—C3A	119.50 (13)	C3—C4—C5	116.54 (13)
N4A—C4A—C5A	119.71 (13)	N5—C5—C4	117.97 (12)
C3A—C4A—C5A	120.79 (14)	N5—C5—C6	119.34 (12)
C4A—C5A—C6A	119.46 (15)	C4—C5—C6	122.66 (12)
C1A—C6A—C5A	121.45 (16)	C1—C6—C5	119.53 (12)
O11A—C21A—C31A	109.07 (13)	O11—C11—O12	125.45 (14)
C1A—C31A—C21A	115.58 (14)	O11—C11—C1	117.05 (14)
C3A—C2A—H2A	119.00	O12—C11—C1	117.50 (13)
C1A—C2A—H2A	119.00	C1—C2—H2	120.00
C2A—C3A—H3A	120.00	C3—C2—H2	120.00
C4A—C3A—H3A	120.00	C3—C4—H4	122.00
C4A—C5A—H5A	120.00	C5—C4—H4	122.00
C6A—C5A—H5A	120.00	C1—C6—H6	120.00
C5A—C6A—H6A	119.00	C5—C6—H6	120.00

O32—N3—C3—C2	−161.49 (14)	C4A—C5A—C6A—C1A	0.8 (2)
O32—N3—C3—C4	16.9 (2)	O11A—C21A—C31A—C1A	−65.65 (18)
O31—N3—C3—C2	19.7 (2)	C6—C1—C2—C3	0.9 (2)
O31—N3—C3—C4	−161.93 (14)	C11—C1—C2—C3	−177.57 (13)
O51—N5—C5—C4	3.63 (19)	C2—C1—C6—C5	−1.49 (19)
O52—N5—C5—C6	1.02 (18)	C11—C1—C6—C5	176.97 (13)
O51—N5—C5—C6	−178.10 (12)	C2—C1—C11—O11	−172.71 (13)
O52—N5—C5—C4	−177.25 (13)	C2—C1—C11—O12	7.4 (2)
C6A—C1A—C2A—C3A	−0.2 (2)	C6—C1—C11—O11	8.8 (2)
C31A—C1A—C2A—C3A	−178.02 (15)	C6—C1—C11—O12	−171.08 (13)
C2A—C1A—C6A—C5A	−0.6 (2)	C1—C2—C3—N3	178.42 (13)
C31A—C1A—C6A—C5A	177.21 (15)	C1—C2—C3—C4	0.1 (2)
C2A—C1A—C31A—C21A	−51.8 (2)	N3—C3—C4—C5	−178.87 (13)
C6A—C1A—C31A—C21A	130.51 (16)	C2—C3—C4—C5	−0.6 (2)
C1A—C2A—C3A—C4A	0.9 (3)	C3—C4—C5—N5	178.18 (13)
C2A—C3A—C4A—C5A	−0.7 (2)	C3—C4—C5—C6	0.0 (2)
C2A—C3A—C4A—N4A	−179.93 (16)	N5—C5—C6—C1	−177.13 (12)
N4A—C4A—C5A—C6A	179.12 (14)	C4—C5—C6—C1	1.1 (2)
C3A—C4A—C5A—C6A	−0.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O11A—H11A···O11ⁱ	0.89 (2)	1.88 (2)	2.7569 (16)	168 (2)
N4A—H41A···O12	0.958 (19)	1.924 (19)	2.845 (2)	160.8 (17)
N4A—H42A···O11ⁱⁱ	0.936 (19)	2.02 (2)	2.8905 (19)	154.0 (18)
N4A—H42A···O12ⁱⁱ	0.936 (19)	2.53 (2)	3.1033 (18)	119.9 (14)
N4A—H43A···O11Aⁱⁱⁱ	1.005 (19)	1.783 (19)	2.785 (2)	174.4 (19)
C5A—H5A···O11A^iv	0.93	2.43	3.317 (2)	161

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

Experimental details

Crystal data
Chemical formula	C₈H₁₂NO⁺·C₇H₃N₂O₆⁻
M_r	349.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	297
a, b, c (Å)	15.9566 (19), 5.7844 (5), 17.4118 (14)
β (°)	102.811 (10)
V (Å³)	1567.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.30 × 0.30 × 0.25

Data collection
Diffractometer	Oxford Diffraction Gemini-S CCD-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.950, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	5928, 3061, 2203
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.099, 0.98
No. of reflections	3061
No. of parameters	242
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.17

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O11A—H11A···O11ⁱ	0.89 (2)	1.88 (2)	2.7569 (16)	168 (2)
N4A—H41A···O12	0.958 (19)	1.924 (19)	2.845 (2)	160.8 (17)
N4A—H42A···O11ⁱⁱ	0.936 (19)	2.02 (2)	2.8905 (19)	154.0 (18)
N4A—H42A···O12ⁱⁱ	0.936 (19)	2.53 (2)	3.1033 (18)	119.9 (14)
N4A—H43A···O11Aⁱⁱⁱ	1.005 (19)	1.783 (19)	2.785 (2)	174.4 (19)
C5A—H5A···O11A^iv	0.9300	2.4300	3.317 (2)	161.00

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

Acknowledgements

The authors acknowledge financial support from the Australian Research Council and the School of Physical and Chemical Sciences, Queensland University of Technology.

References

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