1,4-Dimethyl­piperazin-1-ium 3-hy­droxy-2-naphtho­ate

Craig, G.E.; Johnson, C.; Kennedy, A.R.

doi:10.1107/S1600536812005375

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o787

doi:10.1107/S1600536812005375

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1,4-Dimethylpiperazin-1-ium 3-hydroxy-2-naphthoate

Gemma E. Craig,^a Carla Johnson ^a and Alan R. Kennedy ^a ^*

^aDepartment of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland
^*Correspondence e-mail: a.r.kennedy@strath.ac.uk

(Received 31 January 2012; accepted 7 February 2012; online 17 February 2012)

The reaction of 1,4-dimethylpiperazine and 3-hydroxy-2-naphthoic acid gives the title 1:1 salt, C₆H₁₅N₂⁺·C₁₁H₇O₃⁻, with a singly protonated piperazinium cation. In the crystal, a single N—H⋯O hydrogen bond links the cations and anions into discrete pairs and the aromatic anions stack along the crystallographic a-axis direction. This results in layers of cations and anions alternating along the crystallographic c-axis direction. An intramolecular O—H⋯O hydrogen bond is also present.

Related literature

For general descriptions of the salt selection process in the pharmacy industry, see: Stahl & Wermuth (2002 ); Gould (1986 ); Serajuddin (2007 ). For structures of monoprotonated 1,4-dimethylpiperazinium, see: Clemente et al. (1999 ); Marzotto et al. (2001 ). For systematic structural studies of structure–property relationships of salts in a pharmaceutical context, see: Arlin et al. (2011 ); Kennedy et al. (2011 ). For the Cambridge Structural Database, see: Allen (2002 ). For a related aryl carboxylate structure, see: Burchell et al. (2001 ).

Experimental

Crystal data

C₆H₁₅N₂⁺·C₁₁H₇O₃⁻
M_r = 302.37
Monoclinic, P 2₁
a = 5.8772 (16) Å
b = 10.892 (2) Å
c = 12.562 (2) Å
β = 100.29 (2)°
V = 791.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.15 × 0.08 mm

Data collection

Oxford Diffraction Xcaliber S diffractometer
7855 measured reflections
2996 independent reflections
1608 reflections with I > 2σ(I)
R_int = 0.119

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.121
S = 0.83
2996 reflections
203 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 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
O3—H3⋯O2	0.82	1.81	2.541 (3)	148
N2—H2⋯O1ⁱ	0.91	1.71	2.613 (3)	174
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

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: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and X-SEED (Barbour, 2001 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812005375/lh5414sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005375/lh5414Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005375/lh5414Isup3.cml

checkCIF report

Comment top

The influence of solid-state structure on salt selection in the pharmacy industry is of ongoing interest and importance (Stahl & Wermuth, 2002; Gould, 1986; Serajuddin, 2007). As a contribution towards this we have recently investigated series of salt structures based on both protonated tertiary amines and anions derived from aryl carboxylic acids (Arlin et al., 2011; Kennedy et al., 2011). Combining these two themes we present here the structure of 1,4-dimethylpiperazinium 3-hydroxy-2-naphthoate (I).

Reaction of equimolar amounts of 1,4-dimethylpiperazine and 3-hydroxy-2-naphthoic acid in an aqueous environment gave a 1:1 salt with the base monoprotonated to give 1,4-dimethylpiperazinium, see Fig. 1. A search of the Cambridge Structural Database (Allen, 2002) found only three other examples of structures containing the monoprotonated base. All were RMCl₃ structures (M = Co, Cu, Zn) with the non-protonated amine forming a bond to the metal centre (Clemente et al., 1999; Marzotto et al., 2001). In contrast there were 54 hits for the di-protonated cation, [C₆N₂H₁₆]²⁺, with organic anions. This later group includes all the carboxylate based anions, including the only other aryl-carboxylate reported (Burchell et al., 2001). The molecular geometries of both ions in (I) are unexceptional. The near equal C—O lengths of the carboxylate group confirm its deprotonated nature. The piperazine ring exists in a chair conformation with equatorial methyl groups. Note that the C—N bond lengths of the protonated N2 atom are systematically longer than those involving the neutral atom N1.

Both potential hydrogen bond donors are utilized. The hydroxy group makes an internal hydrogen bond with one O atom of the carboxylate group whilst the the second O atom accepts an intermolecular hydrogen bond from NH of the cation, Table 1. This relatively limited hydrogen bonding results only in discrete cation-anion pairs being formed with no extended hydrogen bonding network. The aromatic anions stack along the crystallographic a direction in an offset manner such that the closest contact is between C2 of the carboxylate substituted ring and C11 of the non-substituted ring (C2···C11' = 3.576 (4) Å, ' = x + 1, y, z). The polar orientation of neighbouring anion stacks is reversed along the crystallographic c direction and this results in alternating layers of anions and cations as shown in Fig. 2.

Related literature top

For salt selection in the pharmacy industry, see: Stahl & Wermuth (2002); Gould (1986); Serajuddin (2007). For structures of monoprotonated 1,4-dimethylpiperazinium, see: Clemente et al. (1999); Marzotto et al. (2001). For systematic structural studies of structure–property relationships of salts in a pharmaceutical context, see: Arlin et al. (2011); Kennedy et al. (2011). For the Cambridge Structural Database, see: Allen (2002). For a related aryl carboxylate structure, see: Burchell et al. (2001).

Experimental top

Addition of an equimolar amount of 1,4-dimethylpiperazine to an aqueous slurry of 3-hydroxy-2-naphthoic acid with stirring and heating to 323 K gave a clear solution. After cooling to room temperature, colourless crystals of (I) were deposited after 3 days.

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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and X-SEED (Barbour, 2001).

Figures top

	Fig. 1. Contents of the asymmetric unit of (I). Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. Packing of (I) viewed along the a direction. Note the stacked anions down the a direction and the layers of cations and anions that alternate along the c direction.

1,4-Dimethylpiperazinium 3-hydroxy-2-naphthoate top

Crystal data top

C₆H₁₅N₂⁺·C₁₁H₇O₃⁻	F(000) = 324
M_r = 302.37	D_x = 1.269 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1466 reflections
a = 5.8772 (16) Å	θ = 2.5–31.3°
b = 10.892 (2) Å	µ = 0.09 mm⁻¹
c = 12.562 (2) Å	T = 293 K
β = 100.29 (2)°	Fragment, colourless
V = 791.2 (3) Å³	0.20 × 0.15 × 0.08 mm
Z = 2

Data collection top

Oxford Diffraction Xcaliber S diffractometer	1608 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.119
Graphite monochromator	θ_max = 26.0°, θ_min = 2.5°
Detector resolution: 16.0268 pixels mm^-1	h = −7→7
ω scans	k = −13→13
7855 measured reflections	l = −15→15
2996 independent reflections

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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.0613P)²] where P = (F_o² + 2F_c²)/3
S = 0.83	(Δ/σ)_max < 0.001
2996 reflections	Δρ_max = 0.14 e Å⁻³
203 parameters	Δρ_min = −0.16 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.046 (5)

Crystal data top

C₆H₁₅N₂⁺·C₁₁H₇O₃⁻	V = 791.2 (3) Å³
M_r = 302.37	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.8772 (16) Å	µ = 0.09 mm⁻¹
b = 10.892 (2) Å	T = 293 K
c = 12.562 (2) Å	0.20 × 0.15 × 0.08 mm
β = 100.29 (2)°

Data collection top

Oxford Diffraction Xcaliber S diffractometer	1608 reflections with I > 2σ(I)
7855 measured reflections	R_int = 0.119
2996 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.121	H-atom parameters constrained
S = 0.83	Δρ_max = 0.14 e Å⁻³
2996 reflections	Δρ_min = −0.16 e Å⁻³
203 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.4807 (4)	0.4173 (2)	0.83756 (18)	0.0698 (7)
O2	0.7191 (4)	0.2587 (2)	0.86723 (18)	0.0693 (7)
O3	0.6220 (4)	0.0581 (2)	0.7662 (2)	0.0713 (7)
H3	0.6909	0.1050	0.8120	0.107*
N1	0.0615 (5)	0.2188 (2)	0.18076 (18)	0.0540 (7)
N2	0.2028 (4)	0.0436 (2)	0.03575 (18)	0.0485 (6)
H2	0.3079	0.0004	0.0834	0.058*
C1	0.5324 (6)	0.3081 (3)	0.8212 (2)	0.0499 (8)
C2	0.3691 (5)	0.2334 (2)	0.7444 (2)	0.0421 (7)
C3	0.4223 (5)	0.1106 (3)	0.7177 (2)	0.0492 (8)
C4	0.2712 (6)	0.0446 (3)	0.6450 (2)	0.0577 (8)
H4	0.3089	−0.0353	0.6286	0.069*
C5	0.0600 (6)	0.0946 (3)	0.5943 (2)	0.0511 (8)
C6	0.0011 (5)	0.2159 (3)	0.6212 (2)	0.0481 (8)
C7	0.1630 (5)	0.2818 (2)	0.6959 (2)	0.0460 (7)
H7	0.1275	0.3618	0.7128	0.055*
C8	−0.1018 (7)	0.0297 (3)	0.5177 (3)	0.0691 (10)
H8	−0.0694	−0.0504	0.4995	0.083*
C9	−0.3021 (7)	0.0825 (4)	0.4708 (3)	0.0819 (12)
H9	−0.4035	0.0387	0.4192	0.098*
C10	−0.3613 (7)	0.2015 (4)	0.4978 (3)	0.0815 (12)
H10	−0.5014	0.2359	0.4653	0.098*
C11	−0.2116 (6)	0.2662 (3)	0.5721 (3)	0.0642 (9)
H11	−0.2509	0.3450	0.5907	0.077*
C12	0.2864 (6)	0.2257 (3)	0.1499 (3)	0.0621 (9)
H12A	0.3974	0.1803	0.2017	0.074*
H12B	0.3362	0.3107	0.1514	0.074*
C13	0.2821 (6)	0.1748 (3)	0.0404 (3)	0.0582 (9)
H13A	0.4357	0.1793	0.0224	0.070*
H13B	0.1784	0.2230	−0.0123	0.070*
C14	−0.0210 (5)	0.0334 (3)	0.0721 (2)	0.0559 (8)
H14A	−0.0635	−0.0524	0.0751	0.067*
H14B	−0.1396	0.0745	0.0208	0.067*
C15	−0.0076 (6)	0.0901 (3)	0.1817 (2)	0.0572 (9)
H15A	−0.1573	0.0843	0.2036	0.069*
H15B	0.1034	0.0454	0.2339	0.069*
C16	0.0568 (7)	0.2757 (3)	0.2852 (3)	0.0778 (11)
H16A	0.1569	0.2313	0.3408	0.117*
H16B	−0.0983	0.2742	0.2995	0.117*
H16C	0.1086	0.3592	0.2841	0.117*
C17	0.1976 (6)	−0.0108 (3)	−0.0721 (2)	0.0694 (10)
H17A	0.1472	−0.0946	−0.0717	0.104*
H17B	0.3498	−0.0079	−0.0898	0.104*
H17C	0.0926	0.0347	−0.1249	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0622 (15)	0.0473 (14)	0.0920 (16)	0.0018 (12)	−0.0080 (11)	−0.0174 (12)
O2	0.0633 (17)	0.0680 (15)	0.0704 (14)	0.0035 (13)	−0.0053 (12)	−0.0016 (12)
O3	0.0711 (16)	0.0539 (14)	0.0857 (16)	0.0150 (13)	0.0058 (12)	0.0047 (12)
N1	0.0617 (18)	0.0417 (15)	0.0584 (15)	0.0002 (14)	0.0099 (12)	0.0000 (12)
N2	0.0493 (15)	0.0434 (14)	0.0510 (14)	0.0044 (12)	0.0042 (10)	0.0066 (12)
C1	0.049 (2)	0.047 (2)	0.0516 (18)	−0.0045 (16)	0.0016 (15)	0.0030 (15)
C2	0.0478 (18)	0.0365 (15)	0.0419 (15)	−0.0003 (14)	0.0074 (13)	0.0016 (13)
C3	0.055 (2)	0.0392 (17)	0.0534 (17)	0.0029 (15)	0.0085 (15)	0.0040 (15)
C4	0.079 (2)	0.0358 (16)	0.062 (2)	0.0007 (18)	0.0225 (17)	−0.0012 (15)
C5	0.066 (2)	0.0445 (19)	0.0440 (16)	−0.0126 (16)	0.0121 (15)	−0.0028 (14)
C6	0.0483 (19)	0.0502 (19)	0.0452 (15)	−0.0061 (15)	0.0069 (14)	0.0008 (15)
C7	0.057 (2)	0.0347 (15)	0.0462 (15)	0.0011 (15)	0.0089 (14)	−0.0039 (12)
C8	0.086 (3)	0.062 (2)	0.059 (2)	−0.021 (2)	0.0122 (19)	−0.0126 (18)
C9	0.078 (3)	0.101 (3)	0.061 (2)	−0.034 (3)	−0.0001 (19)	−0.008 (2)
C10	0.068 (3)	0.105 (3)	0.065 (2)	−0.015 (2)	−0.0048 (19)	0.013 (2)
C11	0.061 (2)	0.065 (2)	0.0631 (19)	0.0012 (19)	0.0015 (16)	0.0026 (17)
C12	0.065 (2)	0.0412 (18)	0.078 (2)	−0.0092 (17)	0.0058 (17)	0.0020 (17)
C13	0.063 (2)	0.0390 (17)	0.074 (2)	−0.0047 (16)	0.0165 (16)	0.0120 (15)
C14	0.0497 (19)	0.0503 (18)	0.067 (2)	−0.0031 (15)	0.0078 (15)	0.0032 (16)
C15	0.064 (2)	0.050 (2)	0.0585 (19)	−0.0035 (16)	0.0110 (16)	0.0051 (15)
C16	0.098 (3)	0.067 (2)	0.067 (2)	0.004 (2)	0.0124 (19)	−0.0089 (18)
C17	0.082 (3)	0.068 (2)	0.058 (2)	0.013 (2)	0.0097 (17)	0.0025 (18)

Geometric parameters (Å, º) top

O1—C1	1.253 (4)	C8—H8	0.9300
O2—C1	1.265 (4)	C9—C10	1.399 (6)
O3—C3	1.349 (4)	C9—H9	0.9300
O3—H3	0.8200	C10—C11	1.360 (5)
N1—C12	1.445 (4)	C10—H10	0.9300
N1—C16	1.455 (4)	C11—H11	0.9300
N1—C15	1.460 (4)	C12—C13	1.479 (5)
N2—C14	1.472 (4)	C12—H12A	0.9700
N2—C17	1.474 (4)	C12—H12B	0.9700
N2—C13	1.501 (4)	C13—H13A	0.9700
N2—H2	0.9100	C13—H13B	0.9700
C1—C2	1.479 (4)	C14—C15	1.497 (4)
C2—C7	1.361 (4)	C14—H14A	0.9700
C2—C3	1.427 (4)	C14—H14B	0.9700
C3—C4	1.360 (4)	C15—H15A	0.9700
C4—C5	1.400 (4)	C15—H15B	0.9700
C4—H4	0.9300	C16—H16A	0.9600
C5—C8	1.416 (4)	C16—H16B	0.9600
C5—C6	1.421 (4)	C16—H16C	0.9600
C6—C11	1.403 (4)	C17—H17A	0.9600
C6—C7	1.408 (4)	C17—H17B	0.9600
C7—H7	0.9300	C17—H17C	0.9600
C8—C9	1.348 (5)

C3—O3—H3	109.5	C10—C11—C6	121.1 (4)
C12—N1—C16	112.7 (3)	C10—C11—H11	119.5
C12—N1—C15	108.7 (2)	C6—C11—H11	119.5
C16—N1—C15	110.6 (3)	N1—C12—C13	111.5 (3)
C14—N2—C17	112.5 (2)	N1—C12—H12A	109.3
C14—N2—C13	110.4 (2)	C13—C12—H12A	109.3
C17—N2—C13	111.9 (2)	N1—C12—H12B	109.3
C14—N2—H2	107.2	C13—C12—H12B	109.3
C17—N2—H2	107.2	H12A—C12—H12B	108.0
C13—N2—H2	107.2	C12—C13—N2	110.3 (3)
O1—C1—O2	123.0 (3)	C12—C13—H13A	109.6
O1—C1—C2	118.8 (3)	N2—C13—H13A	109.6
O2—C1—C2	118.2 (3)	C12—C13—H13B	109.6
C7—C2—C3	118.2 (3)	N2—C13—H13B	109.6
C7—C2—C1	120.1 (3)	H13A—C13—H13B	108.1
C3—C2—C1	121.7 (3)	N2—C14—C15	110.6 (2)
O3—C3—C4	119.4 (3)	N2—C14—H14A	109.5
O3—C3—C2	120.1 (3)	C15—C14—H14A	109.5
C4—C3—C2	120.6 (3)	N2—C14—H14B	109.5
C3—C4—C5	121.3 (3)	C15—C14—H14B	109.5
C3—C4—H4	119.4	H14A—C14—H14B	108.1
C5—C4—H4	119.4	N1—C15—C14	111.0 (2)
C4—C5—C8	123.2 (3)	N1—C15—H15A	109.4
C4—C5—C6	119.2 (3)	C14—C15—H15A	109.4
C8—C5—C6	117.6 (3)	N1—C15—H15B	109.4
C11—C6—C7	122.5 (3)	C14—C15—H15B	109.4
C11—C6—C5	119.6 (3)	H15A—C15—H15B	108.0
C7—C6—C5	117.9 (3)	N1—C16—H16A	109.5
C2—C7—C6	122.8 (3)	N1—C16—H16B	109.5
C2—C7—H7	118.6	H16A—C16—H16B	109.5
C6—C7—H7	118.6	N1—C16—H16C	109.5
C9—C8—C5	120.8 (4)	H16A—C16—H16C	109.5
C9—C8—H8	119.6	H16B—C16—H16C	109.5
C5—C8—H8	119.6	N2—C17—H17A	109.5
C8—C9—C10	121.7 (3)	N2—C17—H17B	109.5
C8—C9—H9	119.2	H17A—C17—H17B	109.5
C10—C9—H9	119.2	N2—C17—H17C	109.5
C11—C10—C9	119.2 (4)	H17A—C17—H17C	109.5
C11—C10—H10	120.4	H17B—C17—H17C	109.5
C9—C10—H10	120.4

O1—C1—C2—C7	−2.5 (5)	C5—C6—C7—C2	−1.4 (4)
O2—C1—C2—C7	177.8 (3)	C4—C5—C8—C9	−179.6 (3)
O1—C1—C2—C3	176.7 (3)	C6—C5—C8—C9	1.2 (5)
O2—C1—C2—C3	−3.0 (4)	C5—C8—C9—C10	−1.8 (6)
C7—C2—C3—O3	−178.2 (3)	C8—C9—C10—C11	0.9 (6)
C1—C2—C3—O3	2.6 (4)	C9—C10—C11—C6	0.5 (6)
C7—C2—C3—C4	0.6 (4)	C7—C6—C11—C10	178.0 (3)
C1—C2—C3—C4	−178.6 (3)	C5—C6—C11—C10	−1.0 (5)
O3—C3—C4—C5	178.8 (3)	C16—N1—C12—C13	−176.1 (3)
C2—C3—C4—C5	−0.1 (4)	C15—N1—C12—C13	60.9 (3)
C3—C4—C5—C8	179.6 (3)	N1—C12—C13—N2	−58.3 (4)
C3—C4—C5—C6	−1.2 (4)	C14—N2—C13—C12	54.3 (3)
C4—C5—C6—C11	−179.0 (3)	C17—N2—C13—C12	−179.6 (3)
C8—C5—C6—C11	0.2 (4)	C17—N2—C14—C15	−179.8 (3)
C4—C5—C6—C7	1.9 (4)	C13—N2—C14—C15	−54.0 (3)
C8—C5—C6—C7	−178.9 (3)	C12—N1—C15—C14	−60.2 (3)
C3—C2—C7—C6	0.1 (4)	C16—N1—C15—C14	175.6 (3)
C1—C2—C7—C6	179.3 (3)	N2—C14—C15—N1	57.8 (3)
C11—C6—C7—C2	179.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.81	2.541 (3)	148
N2—H2···O1ⁱ	0.91	1.71	2.613 (3)	174

Symmetry code: (i) −x+1, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₆H₁₅N₂⁺·C₁₁H₇O₃⁻
M_r	302.37
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	5.8772 (16), 10.892 (2), 12.562 (2)
β (°)	100.29 (2)
V (Å³)	791.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.15 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcaliber S diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7855, 2996, 1608
R_int	0.119
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.121, 0.83
No. of reflections	2996
No. of parameters	203
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.16
Absolute structure parameter	0.2 (18)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and X-SEED (Barbour, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.81	2.541 (3)	147.8
N2—H2···O1ⁱ	0.91	1.71	2.613 (3)	174.4

Symmetry code: (i) −x+1, y−1/2, −z+1.

References

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Volume 68| Part 3| March 2012| Page o787

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