Triethyl­ammonium (2R,3R)-2,3-bis­(benzo­yloxy)-3-carb­oxy­propano­ate

Li, S.-J.; Zhang, R.-J.; Hou, G.-F.; Li, G.-M.; Yan, P.-F.

doi:10.1107/S1600536812004308

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o651

doi:10.1107/S1600536812004308

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Triethylammonium (2R,3R)-2,3-bis(benzoyloxy)-3-carboxypropanoate

Shang-Ju Li,^a Rong-Jia Zhang,^a Guang-Feng Hou,^a Guang-Ming Li ^a ^* and Peng-Fei Yan ^a

^aKey Laboratory of Functional Inorganic Material Chemistry (HLJU), Ministry of Education, and School of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: gmli_2000@163.com

(Received 22 December 2011; accepted 1 February 2012; online 10 February 2012)

In the anion of the title salt, C₆H₁₆N⁺·C₁₈H₁₃O₈⁻, one of the carboxyl groups is deprotonated. Its O atoms are involved in intermolecular hydrogen bonding with the carboxyl group of an adjacent anion and the amino group of an adjacent cation. The two benzoyloxy rings are oriented with respect to each other at a dihedral angle of 79.46 (6)°.

Related literature

For background to tartaric acid derivatives, see: Kassai et al. (2000 ); Tan et al. (2006 ).

Experimental

Crystal data

C₆H₁₆N⁺·C₁₈H₁₃O₈⁻
M_r = 459.48
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.2148 (12) Å
b = 12.9835 (13) Å
c = 15.9499 (17) Å
V = 2322.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
17272 measured reflections
3242 independent reflections
2336 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.095
S = 1.02
3242 reflections
309 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H101⋯O4ⁱ	0.95 (3)	1.82 (3)	2.770 (3)	177 (3)
O5—H51⋯O3ⁱⁱ	0.93 (4)	1.60 (3)	2.525 (2)	171 (3)
Symmetry codes: (i) x-1, y, z; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812004308/xu5427sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004308/xu5427Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812004308/xu5427Isup3.cml

checkCIF report

Comment top

Optically active tartaric acid and its acyl derivatives (e.g. diacetyl, dibenzoyl, di-p-toluyl) continue to be widely used in the resolution of racemates. Their resolving power is connected with the ability to form diastereomeric salts with racemic amines and hydrazides. (2R,3R)-O,O'-Dibenzoyl-tartaric acid (DBTA) has been known as a chiral selector of enantiomers, such as ephedrine, chiral alcohols and N-methylamphetamine. It was also observed that DBTA can form complexes with some alcohols and aminos; the complex forming properties of DBTA have been investigated (Kassai et al., 2000; Tan et al., 2006).

The asymmertric unit of title compound contains one (2R,3R)-O,O'-dibenzoyl-tartrate anion and one triethylamine cation. In the anion, the two benzene rings make a dihedral angle of 79.46 (6)° (Fig. 1). In the crystal packing, intermoleculear O—H···O and N—H···O hydrogen bonds link these cations and anions into chain structures along [010] (Fig. 2, Table 1).

Related literature top

For background to tartaric acid derivatives, see: Kassai et al. (2000); Tan et al. (2006).

Experimental top

(2R,3R)-O,O'-Dibenzoyl-tartaric acid was a commercially available compound and used as received without further purification. (2R,3R)-O,O'-Dibenzoyl-tartaric acid (0.358 g, 1.0 mmol) and triethylamine (1 mL, 2 mol/L) were dissolved in methanol (8 mL), and the solution was stirring for 10 min at room temperature. And then, the solution was stood at room temperature for a few days, colorless block crystals of title compound were obtained (yield 27%).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. A partial packing view, showing the hydrogen bonding chain structure along [010].

Triethylammonium (2R,3R)-2,3-bis(benzoyloxy)-3-carboxypropanoate top

Crystal data top

C₆H₁₆N⁺·C₁₈H₁₃O₈⁻	F(000) = 976
M_r = 459.48	D_x = 1.314 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 17618 reflections
a = 11.2148 (12) Å	θ = 2.4–28.3°
b = 12.9835 (13) Å	µ = 0.10 mm⁻¹
c = 15.9499 (17) Å	T = 293 K
V = 2322.4 (4) Å³	Block, colorless
Z = 4	0.20 × 0.20 × 0.18 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2336 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.067
Graphite monochromator	θ_max = 28.3°, θ_min = 2.4°
ω scan	h = −14→14
17272 measured reflections	k = −17→17
3242 independent reflections	l = −21→18

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0431P)² + 0.0369P] where P = (F_o² + 2F_c²)/3
3242 reflections	(Δ/σ)_max < 0.001
309 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₆H₁₆N⁺·C₁₈H₁₃O₈⁻	V = 2322.4 (4) Å³
M_r = 459.48	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.2148 (12) Å	µ = 0.10 mm⁻¹
b = 12.9835 (13) Å	T = 293 K
c = 15.9499 (17) Å	0.20 × 0.20 × 0.18 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2336 reflections with I > 2σ(I)
17272 measured reflections	R_int = 0.067
3242 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.20 e Å⁻³
3242 reflections	Δρ_min = −0.21 e Å⁻³
309 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. merg 4 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 > 2sigma(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
C1	0.8315 (2)	0.31475 (18)	0.91650 (17)	0.0256 (6)
C2	0.7651 (2)	0.3345 (2)	0.98812 (17)	0.0318 (6)
H2	0.7737	0.3971	1.0157	0.038*
C3	0.6859 (3)	0.2615 (2)	1.01896 (18)	0.0355 (7)
H3	0.6412	0.2752	1.0668	0.043*
C4	0.6740 (2)	0.1687 (2)	0.97802 (19)	0.0366 (7)
H4	0.6215	0.1195	0.9988	0.044*
C5	0.7395 (2)	0.14762 (19)	0.90625 (18)	0.0329 (6)
H5	0.7306	0.0848	0.8790	0.039*
C6	0.8185 (2)	0.22080 (18)	0.87521 (17)	0.0272 (6)
H6	0.8625	0.2071	0.8271	0.033*
C7	0.9139 (2)	0.3955 (2)	0.88549 (16)	0.0267 (6)
C8	1.0565 (2)	0.43421 (16)	0.77853 (17)	0.0239 (5)
H8	1.0692	0.4933	0.8157	0.029*
C9	1.1775 (2)	0.38534 (17)	0.75872 (16)	0.0241 (5)
C10	0.9965 (2)	0.47203 (17)	0.69826 (16)	0.0237 (5)
H10	1.0568	0.5027	0.6614	0.028*
C11	0.8990 (2)	0.55163 (17)	0.71601 (18)	0.0273 (6)
C12	0.9025 (2)	0.3985 (2)	0.58089 (18)	0.0283 (6)
C13	0.8401 (2)	0.30655 (18)	0.54713 (17)	0.0284 (6)
C14	0.8626 (2)	0.2078 (2)	0.5773 (2)	0.0362 (7)
H14	0.9170	0.1978	0.6205	0.043*
C15	0.8031 (3)	0.1247 (2)	0.5423 (2)	0.0437 (8)
H15	0.8191	0.0584	0.5614	0.052*
C16	0.7203 (3)	0.1396 (2)	0.4795 (2)	0.0432 (8)
H16	0.6806	0.0834	0.4566	0.052*
C17	0.6964 (3)	0.2369 (2)	0.45069 (19)	0.0411 (7)
H17	0.6394	0.2467	0.4091	0.049*
C18	0.7572 (2)	0.3209 (2)	0.48357 (18)	0.0363 (7)
H18	0.7423	0.3867	0.4630	0.044*
C19	0.5614 (2)	0.4077 (2)	0.7214 (2)	0.0410 (7)
H19A	0.6369	0.3714	0.7220	0.049*
H19B	0.5653	0.4619	0.7631	0.049*
C20	0.5432 (3)	0.4554 (3)	0.6361 (2)	0.0549 (9)
H20A	0.4659	0.4871	0.6337	0.082*
H20B	0.5486	0.4030	0.5938	0.082*
H20C	0.6034	0.5066	0.6265	0.082*
C21	0.4518 (3)	0.2449 (2)	0.6854 (2)	0.0455 (8)
H21A	0.4350	0.2709	0.6296	0.055*
H21B	0.3841	0.2037	0.7029	0.055*
C22	0.5604 (3)	0.1767 (2)	0.6811 (3)	0.0685 (11)
H22A	0.5752	0.1471	0.7353	0.103*
H22B	0.6281	0.2168	0.6641	0.103*
H22C	0.5470	0.1226	0.6411	0.103*
C23	0.4718 (3)	0.2984 (2)	0.83353 (18)	0.0391 (7)
H23A	0.5499	0.2684	0.8429	0.047*
H23B	0.4129	0.2447	0.8424	0.047*
C24	0.4518 (3)	0.3828 (2)	0.89667 (19)	0.0479 (8)
H24A	0.3797	0.4191	0.8832	0.072*
H24B	0.5179	0.4298	0.8954	0.072*
H24C	0.4451	0.3534	0.9517	0.072*
N1	0.46413 (19)	0.33463 (16)	0.74420 (14)	0.0308 (5)
H101	0.391 (3)	0.372 (2)	0.7409 (18)	0.045 (8)*
O1	0.98006 (14)	0.36173 (11)	0.82011 (11)	0.0255 (4)
O2	0.92394 (19)	0.48083 (14)	0.91440 (14)	0.0451 (6)
O3	1.19370 (14)	0.29069 (12)	0.76840 (12)	0.0313 (4)
O4	1.25517 (14)	0.44777 (12)	0.73477 (13)	0.0334 (4)
O5	0.94968 (15)	0.64074 (12)	0.73381 (13)	0.0339 (4)
H51	0.891 (3)	0.691 (2)	0.735 (2)	0.076 (11)*
O6	0.79444 (15)	0.53471 (14)	0.71332 (15)	0.0447 (6)
O7	0.94704 (15)	0.38233 (11)	0.65836 (11)	0.0270 (4)
O8	0.91205 (18)	0.47972 (14)	0.54453 (13)	0.0425 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0253 (11)	0.0246 (13)	0.0270 (15)	0.0042 (10)	−0.0020 (11)	0.0015 (11)
C2	0.0355 (14)	0.0283 (13)	0.0315 (16)	0.0038 (12)	0.0048 (13)	−0.0028 (12)
C3	0.0363 (14)	0.0421 (16)	0.0283 (17)	0.0065 (13)	0.0100 (13)	0.0046 (13)
C4	0.0322 (14)	0.0350 (15)	0.0426 (18)	−0.0020 (13)	0.0084 (13)	0.0103 (14)
C5	0.0306 (13)	0.0243 (13)	0.0437 (18)	0.0006 (11)	0.0014 (13)	−0.0002 (12)
C6	0.0255 (12)	0.0265 (12)	0.0295 (15)	0.0030 (11)	0.0031 (11)	−0.0018 (11)
C7	0.0268 (13)	0.0246 (13)	0.0285 (15)	0.0013 (11)	−0.0008 (11)	−0.0025 (11)
C8	0.0263 (11)	0.0161 (10)	0.0294 (14)	−0.0049 (10)	0.0002 (12)	−0.0022 (10)
C9	0.0246 (12)	0.0202 (11)	0.0274 (15)	−0.0021 (10)	−0.0035 (11)	0.0014 (10)
C10	0.0243 (12)	0.0172 (10)	0.0296 (15)	−0.0023 (10)	−0.0013 (11)	0.0000 (10)
C11	0.0249 (12)	0.0187 (11)	0.0383 (17)	−0.0009 (10)	−0.0017 (12)	0.0025 (11)
C12	0.0277 (12)	0.0270 (13)	0.0303 (16)	0.0037 (11)	−0.0007 (12)	0.0006 (12)
C13	0.0257 (12)	0.0303 (14)	0.0294 (16)	0.0040 (11)	−0.0025 (12)	−0.0026 (12)
C14	0.0358 (15)	0.0296 (14)	0.0431 (19)	0.0004 (12)	−0.0113 (13)	−0.0021 (13)
C15	0.0478 (17)	0.0294 (14)	0.054 (2)	−0.0012 (14)	−0.0105 (16)	−0.0101 (15)
C16	0.0404 (16)	0.0432 (17)	0.046 (2)	−0.0043 (14)	−0.0063 (15)	−0.0155 (15)
C17	0.0354 (15)	0.0553 (19)	0.0327 (18)	0.0036 (14)	−0.0099 (14)	−0.0102 (15)
C18	0.0354 (14)	0.0421 (16)	0.0314 (17)	0.0063 (13)	−0.0029 (13)	−0.0019 (13)
C19	0.0281 (13)	0.0426 (15)	0.052 (2)	−0.0040 (12)	−0.0004 (15)	0.0036 (15)
C20	0.0392 (17)	0.069 (2)	0.057 (2)	−0.0049 (17)	0.0068 (16)	0.0195 (18)
C21	0.0456 (17)	0.0407 (16)	0.050 (2)	−0.0039 (15)	0.0022 (16)	−0.0131 (15)
C22	0.060 (2)	0.0522 (19)	0.093 (3)	0.0086 (18)	0.020 (2)	−0.022 (2)
C23	0.0418 (16)	0.0371 (15)	0.0383 (18)	0.0030 (13)	−0.0024 (14)	0.0056 (14)
C24	0.0506 (18)	0.0524 (18)	0.0405 (19)	0.0004 (16)	−0.0060 (16)	−0.0023 (15)
N1	0.0242 (10)	0.0305 (11)	0.0378 (15)	0.0030 (9)	−0.0022 (10)	−0.0008 (10)
O1	0.0282 (8)	0.0192 (8)	0.0291 (10)	−0.0022 (7)	0.0072 (8)	−0.0021 (7)
O2	0.0550 (13)	0.0276 (10)	0.0527 (14)	−0.0101 (9)	0.0192 (11)	−0.0143 (10)
O3	0.0269 (9)	0.0192 (8)	0.0477 (12)	0.0003 (7)	0.0017 (9)	0.0023 (9)
O4	0.0238 (8)	0.0243 (8)	0.0522 (13)	−0.0013 (8)	0.0029 (9)	0.0083 (9)
O5	0.0264 (8)	0.0164 (8)	0.0590 (13)	0.0011 (7)	−0.0004 (9)	−0.0024 (9)
O6	0.0221 (9)	0.0313 (9)	0.0805 (17)	−0.0026 (8)	0.0022 (10)	−0.0082 (11)
O7	0.0337 (9)	0.0179 (8)	0.0292 (11)	−0.0028 (7)	−0.0062 (8)	−0.0009 (7)
O8	0.0509 (12)	0.0318 (10)	0.0448 (13)	−0.0052 (9)	−0.0112 (11)	0.0133 (10)

Geometric parameters (Å, º) top

C1—C2	1.388 (4)	C14—H14	0.9300
C1—C6	1.394 (3)	C15—C16	1.380 (4)
C1—C7	1.482 (3)	C15—H15	0.9300
C2—C3	1.389 (4)	C16—C17	1.371 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.377 (4)	C17—C18	1.389 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.387 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—N1	1.491 (3)
C5—C6	1.390 (4)	C19—C20	1.508 (4)
C5—H5	0.9300	C19—H19A	0.9700
C6—H6	0.9300	C19—H19B	0.9700
C7—O2	1.205 (3)	C20—H20A	0.9600
C7—O1	1.353 (3)	C20—H20B	0.9600
C8—O1	1.435 (3)	C20—H20C	0.9600
C8—C10	1.527 (3)	C21—N1	1.502 (3)
C8—C9	1.532 (3)	C21—C22	1.507 (4)
C8—H8	0.9800	C21—H21A	0.9700
C9—O4	1.249 (3)	C21—H21B	0.9700
C9—O3	1.252 (3)	C22—H22A	0.9600
C10—O7	1.439 (3)	C22—H22B	0.9600
C10—C11	1.531 (3)	C22—H22C	0.9600
C10—H10	0.9800	C23—N1	1.503 (4)
C11—O6	1.194 (3)	C23—C24	1.505 (4)
C11—O5	1.320 (3)	C23—H23A	0.9700
C12—O8	1.208 (3)	C23—H23B	0.9700
C12—O7	1.349 (3)	C24—H24A	0.9600
C12—C13	1.485 (3)	C24—H24B	0.9600
C13—C18	1.388 (4)	C24—H24C	0.9600
C13—C14	1.392 (4)	N1—H101	0.95 (3)
C14—C15	1.386 (4)	O5—H51	0.93 (4)

C2—C1—C6	119.6 (2)	C15—C16—H16	119.8
C2—C1—C7	118.6 (2)	C16—C17—C18	120.1 (3)
C6—C1—C7	121.8 (2)	C16—C17—H17	120.0
C1—C2—C3	120.6 (3)	C18—C17—H17	120.0
C1—C2—H2	119.7	C13—C18—C17	119.9 (3)
C3—C2—H2	119.7	C13—C18—H18	120.0
C4—C3—C2	119.4 (3)	C17—C18—H18	120.0
C4—C3—H3	120.3	N1—C19—C20	112.5 (2)
C2—C3—H3	120.3	N1—C19—H19A	109.1
C3—C4—C5	120.9 (2)	C20—C19—H19A	109.1
C3—C4—H4	119.6	N1—C19—H19B	109.1
C5—C4—H4	119.6	C20—C19—H19B	109.1
C4—C5—C6	119.8 (2)	H19A—C19—H19B	107.8
C4—C5—H5	120.1	C19—C20—H20A	109.5
C6—C5—H5	120.1	C19—C20—H20B	109.5
C5—C6—C1	119.8 (2)	H20A—C20—H20B	109.5
C5—C6—H6	120.1	C19—C20—H20C	109.5
C1—C6—H6	120.1	H20A—C20—H20C	109.5
O2—C7—O1	122.8 (2)	H20B—C20—H20C	109.5
O2—C7—C1	125.5 (2)	N1—C21—C22	114.2 (3)
O1—C7—C1	111.7 (2)	N1—C21—H21A	108.7
O1—C8—C10	109.60 (19)	C22—C21—H21A	108.7
O1—C8—C9	110.67 (17)	N1—C21—H21B	108.7
C10—C8—C9	110.5 (2)	C22—C21—H21B	108.7
O1—C8—H8	108.7	H21A—C21—H21B	107.6
C10—C8—H8	108.7	C21—C22—H22A	109.5
C9—C8—H8	108.7	C21—C22—H22B	109.5
O4—C9—O3	125.0 (2)	H22A—C22—H22B	109.5
O4—C9—C8	114.34 (19)	C21—C22—H22C	109.5
O3—C9—C8	120.6 (2)	H22A—C22—H22C	109.5
O7—C10—C8	106.28 (17)	H22B—C22—H22C	109.5
O7—C10—C11	110.67 (19)	N1—C23—C24	113.4 (2)
C8—C10—C11	112.1 (2)	N1—C23—H23A	108.9
O7—C10—H10	109.2	C24—C23—H23A	108.9
C8—C10—H10	109.2	N1—C23—H23B	108.9
C11—C10—H10	109.2	C24—C23—H23B	108.9
O6—C11—O5	126.3 (2)	H23A—C23—H23B	107.7
O6—C11—C10	124.8 (2)	C23—C24—H24A	109.5
O5—C11—C10	108.9 (2)	C23—C24—H24B	109.5
O8—C12—O7	122.9 (2)	H24A—C24—H24B	109.5
O8—C12—C13	124.7 (2)	C23—C24—H24C	109.5
O7—C12—C13	112.4 (2)	H24A—C24—H24C	109.5
C18—C13—C14	119.8 (2)	H24B—C24—H24C	109.5
C18—C13—C12	118.2 (2)	C19—N1—C21	114.1 (2)
C14—C13—C12	122.0 (2)	C19—N1—C23	112.9 (2)
C15—C14—C13	119.4 (3)	C21—N1—C23	110.8 (2)
C15—C14—H14	120.3	C19—N1—H101	107.3 (17)
C13—C14—H14	120.3	C21—N1—H101	106.1 (17)
C16—C15—C14	120.4 (3)	C23—N1—H101	105.0 (18)
C16—C15—H15	119.8	C7—O1—C8	118.11 (18)
C14—C15—H15	119.8	C11—O5—H51	108 (2)
C17—C16—C15	120.3 (3)	C12—O7—C10	114.96 (18)
C17—C16—H16	119.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H101···O4ⁱ	0.95 (3)	1.82 (3)	2.770 (3)	177 (3)
O5—H51···O3ⁱⁱ	0.93 (4)	1.60 (3)	2.525 (2)	171 (3)

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

Experimental details

Crystal data
Chemical formula	C₆H₁₆N⁺·C₁₈H₁₃O₈⁻
M_r	459.48
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	11.2148 (12), 12.9835 (13), 15.9499 (17)
V (Å³)	2322.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	17272, 3242, 2336
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.095, 1.02
No. of reflections	3242
No. of parameters	309
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H101···O4ⁱ	0.95 (3)	1.82 (3)	2.770 (3)	177 (3)
O5—H51···O3ⁱⁱ	0.93 (4)	1.60 (3)	2.525 (2)	171 (3)

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

Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (grant Nos. 20872030 and 20972043) and Heilongjiang University, China.

References

Kassai, C., Juvancz, Z., BaAlint, J., Fogassy, E. & Kozma, D. (2000). Tetrahedron, 56, 8355–8359. Web of Science CrossRef CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tan, B., Luo, G.-S., Qi, X. & Wang, J.-D. (2006). Sep. Purif. Technol. A, 49, 186–191. Web of Science CrossRef CAS Google Scholar