2,2,6,6-Tetra­methyl-4-oxopiperidin-1-ium 4-chloro-3-nitro­benzoate

Yamin, B.M.; Zulkifli, N.Z.

doi:10.1107/S1600536811025074

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1920

doi:10.1107/S1600536811025074

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2,2,6,6-Tetramethyl-4-oxopiperidin-1-ium 4-chloro-3-nitrobenzoate

Bohari M. Yamin ^a ^* and Norsakina Z. Zulkifli ^a

^aSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, UKM 43500 Bangi Selangor, Malaysia
^*Correspondence e-mail: bohari@ukm.my

(Received 8 June 2011; accepted 25 June 2011; online 6 July 2011)

The title salt, C₉H₁₈NO⁺·C₇H₃ClNO₄⁻, was obtained as an unexpected product of the reaction of 4-chloro-3-nitrobenzoyl isothiocyanate with pyrrolidine. The six-membered ring of the 4-oxopiperidinium cation adopts a chair conformation. In the crystal structure, two cations and three anions are linked together by intermolecular N—H⋯O and C—H⋯O hydrogen bonds and arranged diagonally along the ac face.

Related literature

For related structures, see: Wang et al. (2008 ); Jasinski et al. (2009 ), Smith & Wermuth (2011 ). For bond-length data, see Allen et al. (1987 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₉H₁₈NO⁺·C₇H₃ClNO₄⁻
M_r = 356.80
Triclinic, $[P \overline 1]$
a = 7.9974 (10) Å
b = 10.3267 (13) Å
c = 11.9196 (15) Å
α = 109.101 (3)°
β = 96.785 (3)°
γ = 104.720 (3)°
V = 877.58 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 298 K
0.40 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.908, T_max = 0.978
10082 measured reflections
3431 independent reflections
2268 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.126
S = 1.01
3431 reflections
229 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3ⁱ	0.87 (2)	1.89 (2)	2.750 (2)	165
N1—H1B⋯O2ⁱⁱ	0.89 (1)	1.77 (1)	2.653 (2)	171
C3—H3A⋯O4ⁱⁱⁱ	0.97	2.54	3.269 (3)	132
C8—H8B⋯O3ⁱ	0.96	2.54	3.297 (3)	136
Symmetry codes: (i) x-1, y-1, z; (ii) -x+1, -y+1, -z+2; (iii) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811025074/ff2016sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025074/ff2016Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025074/ff2016Isup3.cml

checkCIF report

Comment top

The title salt is an unexpected product of the reaction of 4-chloro-3- nitro-benzoylisothiocyanate with pyrrolidine. The expected product was N-(4-chloro-3-nitrobenzoyl)-N'-(pyrrolidin-1-yl)thiourea. The salt consists of 2,2,6,6-tetramethylpiperidinium-4-one cation and 4-chloro-3-nitrobenzoate anion (Fig.1) indicating the opening of pyrrolidine ring and involvement of acetone solvent in the reaction mechanism. The piperidinium ring adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) Q, θ and ϕ, of 0.507 (2) Å, 3.4 (3)° and 207 (6)°, respectively. The bond lengths and angles are in normal range (Allen et al., 1987) and comparable to those in piperidinium 3-hydroxy-2-naphthoate (Wang et al., 2008) and 4-carbamoylpiperidinium 5-nitrosalicylate (Smith & Wermuth, 2011). All atoms of the benzoate anion are essentially coplanar with the benzene ring except O4 and O5, which are deviated from the plane by 0.690 (2) and 0.880 (2) Å, respectively. In the crystal structure, two cations and three anions are linked together by intermolecular hydrogen bonds (symmetry codes as in Table 2) and arranged diagonally along the ac face (Fig.2).

Related literature top

For related structures, see: Wang et al. (2008); Jasinski et al. (2009), Smith & Wermuth (2011). For bond-length data, see Allen et al. (1987). For puckering parameter, see: Cremer & Pople (1975).

Experimental top

A solution of 4-chloro-3-nitrobenzoylisothiocyanate (2.42 g, 0.01 mol) in 30 ml acetone was added into a flask containing 30 ml acetone solution of pyyrolidine (0.71 g, 0.01 mol).The mixture was refluxed for 1 h. Then, the solution was filtered-off and left to evaporate at room temperature. The colourless solid was obtained after one day of evaporation (yield 83%, m.p 473.1–474.3 K).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsods drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I) viewed down the b axis. Hydrogen bonds are shown by dashed lines.

2,2,6,6-Tetramethyl-4-oxopiperidin-1-ium 4-chloro-3-nitrobenzoate top

Crystal data top

C₉H₁₈NO⁺·C₇H₃ClNO₄⁻	Z = 2
M_r = 356.80	F(000) = 376
Triclinic, P1	D_x = 1.350 Mg m⁻³
Hall symbol: -P 1	Melting point = 447.3–448.1 K
a = 7.9974 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3267 (13) Å	Cell parameters from 1985 reflections
c = 11.9196 (15) Å	θ = 1.8–26.0°
α = 109.101 (3)°	µ = 0.25 mm⁻¹
β = 96.785 (3)°	T = 298 K
γ = 104.720 (3)°	Slab, colourless
V = 877.58 (19) Å³	0.40 × 0.14 × 0.09 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3431 independent reflections
Radiation source: fine-focus sealed tube	2268 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 83.66 pixels mm^-1	θ_max = 26.0°, θ_min = 1.8°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −12→12
T_min = 0.908, T_max = 0.978	l = −14→14
10082 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0655P)² + 0.0942P] where P = (F_o² + 2F_c²)/3
3431 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.25 e Å⁻³
2 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₉H₁₈NO⁺·C₇H₃ClNO₄⁻	γ = 104.720 (3)°
M_r = 356.80	V = 877.58 (19) Å³
Triclinic, P1	Z = 2
a = 7.9974 (10) Å	Mo Kα radiation
b = 10.3267 (13) Å	µ = 0.25 mm⁻¹
c = 11.9196 (15) Å	T = 298 K
α = 109.101 (3)°	0.40 × 0.14 × 0.09 mm
β = 96.785 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3431 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2268 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.978	R_int = 0.030
10082 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	2 restraints
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.25 e Å⁻³
3431 reflections	Δρ_min = −0.18 e Å⁻³
229 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
Cl1	0.10661 (8)	0.44819 (7)	0.35541 (6)	0.0712 (2)
O1	0.1974 (3)	0.1497 (2)	0.57035 (16)	0.0823 (6)
O2	0.7048 (2)	0.76828 (18)	0.88016 (14)	0.0742 (5)
O3	0.7880 (2)	0.93410 (17)	0.80065 (14)	0.0624 (5)
O4	0.3749 (3)	0.8614 (2)	0.41307 (17)	0.0802 (6)
O5	0.3627 (3)	0.6544 (2)	0.28559 (16)	0.0862 (6)
N1	0.1289 (2)	0.11990 (18)	0.88732 (15)	0.0386 (4)
H1A	0.0241 (16)	0.0568 (17)	0.8704 (17)	0.042 (6)*
H1B	0.176 (3)	0.151 (2)	0.9662 (10)	0.052 (6)*
N2	0.3733 (2)	0.7373 (2)	0.38805 (18)	0.0578 (5)
C1	0.2358 (3)	0.0336 (2)	0.81718 (18)	0.0452 (5)
C2	0.0998 (3)	0.2474 (2)	0.86054 (19)	0.0460 (5)
C3	0.0313 (3)	0.1960 (3)	0.7231 (2)	0.0561 (6)
H3A	−0.0898	0.1326	0.7014	0.067*
H3B	0.0300	0.2788	0.7019	0.067*
C4	0.1398 (3)	0.1179 (3)	0.6502 (2)	0.0559 (6)
C5	0.1637 (3)	−0.0069 (3)	0.68090 (19)	0.0575 (6)
H5A	0.2447	−0.0452	0.6356	0.069*
H5B	0.0505	−0.0824	0.6552	0.069*
C6	0.2039 (3)	−0.1004 (2)	0.8498 (2)	0.0587 (6)
H6A	0.2490	−0.0723	0.9354	0.088*
H6B	0.2636	−0.1627	0.8047	0.088*
H6C	0.0791	−0.1504	0.8297	0.088*
C7	0.4326 (3)	0.1167 (3)	0.8553 (2)	0.0642 (7)
H7A	0.4688	0.1553	0.9425	0.096*
H7B	0.4550	0.1943	0.8259	0.096*
H7C	0.4984	0.0532	0.8216	0.096*
C8	−0.0406 (3)	0.2880 (3)	0.9280 (2)	0.0639 (7)
H8A	0.0056	0.3221	1.0141	0.096*
H8B	−0.1435	0.2050	0.9045	0.096*
H8C	−0.0723	0.3627	0.9080	0.096*
C9	0.2697 (3)	0.3757 (2)	0.9055 (2)	0.0682 (7)
H9A	0.3208	0.3943	0.9885	0.102*
H9B	0.2425	0.4593	0.9006	0.102*
H9C	0.3525	0.3541	0.8558	0.102*
C10	0.4375 (3)	0.5931 (2)	0.67661 (19)	0.0457 (5)
H10A	0.4547	0.5605	0.7398	0.055*
C11	0.5459 (2)	0.7263 (2)	0.68617 (17)	0.0379 (5)
C12	0.5203 (2)	0.7728 (2)	0.59146 (17)	0.0410 (5)
H12A	0.5910	0.8622	0.5968	0.049*
C13	0.3893 (3)	0.6860 (2)	0.48870 (18)	0.0419 (5)
C14	0.2792 (3)	0.5541 (2)	0.47945 (18)	0.0442 (5)
C15	0.3041 (3)	0.5083 (2)	0.5742 (2)	0.0501 (5)
H15A	0.2311	0.4200	0.5696	0.060*
C16	0.6921 (3)	0.8182 (2)	0.79869 (18)	0.0444 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0475 (4)	0.0709 (4)	0.0599 (4)	0.0018 (3)	−0.0096 (3)	−0.0004 (3)
O1	0.0921 (14)	0.1105 (15)	0.0579 (11)	0.0264 (11)	0.0259 (10)	0.0492 (11)
O2	0.0933 (13)	0.0718 (11)	0.0368 (9)	0.0035 (10)	−0.0101 (8)	0.0193 (8)
O3	0.0499 (9)	0.0538 (10)	0.0625 (10)	−0.0038 (8)	−0.0101 (8)	0.0179 (8)
O4	0.0923 (14)	0.0673 (12)	0.0808 (13)	0.0234 (10)	−0.0083 (10)	0.0380 (10)
O5	0.1131 (16)	0.0961 (14)	0.0418 (10)	0.0258 (12)	0.0073 (10)	0.0245 (10)
N1	0.0376 (10)	0.0401 (10)	0.0317 (9)	0.0051 (8)	0.0009 (8)	0.0127 (8)
N2	0.0518 (12)	0.0640 (14)	0.0517 (13)	0.0125 (10)	−0.0058 (9)	0.0241 (11)
C1	0.0452 (12)	0.0525 (13)	0.0394 (11)	0.0177 (10)	0.0074 (9)	0.0178 (10)
C2	0.0479 (12)	0.0425 (12)	0.0479 (12)	0.0111 (9)	0.0079 (10)	0.0203 (10)
C3	0.0547 (14)	0.0666 (15)	0.0555 (14)	0.0179 (12)	0.0054 (11)	0.0369 (12)
C4	0.0526 (13)	0.0719 (16)	0.0384 (12)	0.0106 (12)	0.0014 (10)	0.0240 (11)
C5	0.0676 (16)	0.0656 (15)	0.0383 (12)	0.0252 (12)	0.0132 (11)	0.0142 (11)
C6	0.0660 (15)	0.0537 (14)	0.0607 (15)	0.0240 (12)	0.0115 (12)	0.0234 (12)
C7	0.0469 (14)	0.0842 (18)	0.0701 (16)	0.0235 (13)	0.0146 (12)	0.0365 (14)
C8	0.0691 (16)	0.0586 (15)	0.0727 (17)	0.0284 (13)	0.0236 (13)	0.0263 (13)
C9	0.0698 (17)	0.0487 (14)	0.0756 (18)	0.0016 (12)	0.0062 (13)	0.0262 (13)
C10	0.0469 (12)	0.0481 (12)	0.0415 (12)	0.0116 (10)	0.0106 (9)	0.0178 (10)
C11	0.0354 (10)	0.0399 (11)	0.0344 (10)	0.0119 (9)	0.0068 (8)	0.0092 (9)
C12	0.0361 (11)	0.0389 (11)	0.0426 (12)	0.0084 (9)	0.0056 (9)	0.0120 (9)
C13	0.0387 (11)	0.0469 (12)	0.0385 (11)	0.0148 (9)	0.0058 (9)	0.0136 (9)
C14	0.0341 (11)	0.0445 (12)	0.0416 (12)	0.0106 (9)	0.0043 (9)	0.0030 (9)
C15	0.0436 (12)	0.0403 (12)	0.0575 (14)	0.0029 (9)	0.0120 (10)	0.0146 (10)
C16	0.0414 (12)	0.0472 (13)	0.0357 (11)	0.0133 (10)	0.0015 (9)	0.0068 (10)

Geometric parameters (Å, º) top

Cl1—C14	1.726 (2)	C6—H6A	0.9600
O1—C4	1.207 (3)	C6—H6B	0.9600
O2—C16	1.245 (3)	C6—H6C	0.9600
O3—C16	1.238 (3)	C7—H7A	0.9600
O4—N2	1.213 (2)	C7—H7B	0.9600
O5—N2	1.219 (2)	C7—H7C	0.9600
N1—C1	1.514 (3)	C8—H8A	0.9600
N1—C2	1.517 (3)	C8—H8B	0.9600
N1—H1A	0.874 (9)	C8—H8C	0.9600
N1—H1B	0.888 (9)	C9—H9A	0.9600
N2—C13	1.467 (3)	C9—H9B	0.9600
C1—C7	1.520 (3)	C9—H9C	0.9600
C1—C6	1.524 (3)	C10—C15	1.383 (3)
C1—C5	1.536 (3)	C10—C11	1.387 (3)
C2—C8	1.521 (3)	C10—H10A	0.9300
C2—C3	1.529 (3)	C11—C12	1.377 (3)
C2—C9	1.529 (3)	C11—C16	1.516 (3)
C3—C4	1.494 (3)	C12—C13	1.379 (3)
C3—H3A	0.9700	C12—H12A	0.9300
C3—H3B	0.9700	C13—C14	1.383 (3)
C4—C5	1.499 (3)	C14—C15	1.372 (3)
C5—H5A	0.9700	C15—H15A	0.9300
C5—H5B	0.9700

C1—N1—C2	120.56 (16)	H6B—C6—H6C	109.5
C1—N1—H1A	103.8 (13)	C1—C7—H7A	109.5
C2—N1—H1A	106.4 (13)	C1—C7—H7B	109.5
C1—N1—H1B	108.5 (14)	H7A—C7—H7B	109.5
C2—N1—H1B	107.7 (13)	C1—C7—H7C	109.5
H1A—N1—H1B	109.6 (19)	H7A—C7—H7C	109.5
O4—N2—O5	124.2 (2)	H7B—C7—H7C	109.5
O4—N2—C13	117.4 (2)	C2—C8—H8A	109.5
O5—N2—C13	118.4 (2)	C2—C8—H8B	109.5
N1—C1—C7	111.61 (17)	H8A—C8—H8B	109.5
N1—C1—C6	105.17 (17)	C2—C8—H8C	109.5
C7—C1—C6	109.29 (17)	H8A—C8—H8C	109.5
N1—C1—C5	107.97 (16)	H8B—C8—H8C	109.5
C7—C1—C5	111.59 (19)	C2—C9—H9A	109.5
C6—C1—C5	111.04 (18)	C2—C9—H9B	109.5
N1—C2—C8	105.96 (17)	H9A—C9—H9B	109.5
N1—C2—C3	107.28 (17)	C2—C9—H9C	109.5
C8—C2—C3	110.62 (19)	H9A—C9—H9C	109.5
N1—C2—C9	111.61 (17)	H9B—C9—H9C	109.5
C8—C2—C9	109.71 (19)	C15—C10—C11	120.8 (2)
C3—C2—C9	111.51 (19)	C15—C10—H10A	119.6
C4—C3—C2	113.43 (18)	C11—C10—H10A	119.6
C4—C3—H3A	108.9	C12—C11—C10	119.08 (18)
C2—C3—H3A	108.9	C12—C11—C16	120.59 (18)
C4—C3—H3B	108.9	C10—C11—C16	120.33 (18)
C2—C3—H3B	108.9	C11—C12—C13	119.65 (19)
H3A—C3—H3B	107.7	C11—C12—H12A	120.2
O1—C4—C3	122.5 (2)	C13—C12—H12A	120.2
O1—C4—C5	123.1 (2)	C12—C13—C14	121.47 (19)
C3—C4—C5	114.4 (2)	C12—C13—N2	117.49 (18)
C4—C5—C1	113.22 (18)	C14—C13—N2	121.03 (18)
C4—C5—H5A	108.9	C15—C14—C13	118.79 (19)
C1—C5—H5A	108.9	C15—C14—Cl1	118.87 (17)
C4—C5—H5B	108.9	C13—C14—Cl1	122.29 (17)
C1—C5—H5B	108.9	C14—C15—C10	120.2 (2)
H5A—C5—H5B	107.7	C14—C15—H15A	119.9
C1—C6—H6A	109.5	C10—C15—H15A	119.9
C1—C6—H6B	109.5	O3—C16—O2	126.28 (19)
H6A—C6—H6B	109.5	O3—C16—C11	117.47 (19)
C1—C6—H6C	109.5	O2—C16—C11	116.24 (19)
H6A—C6—H6C	109.5

C2—N1—C1—C7	73.0 (2)	C16—C11—C12—C13	178.44 (17)
C2—N1—C1—C6	−168.64 (17)	C11—C12—C13—C14	1.6 (3)
C2—N1—C1—C5	−50.0 (2)	C11—C12—C13—N2	−177.04 (18)
C1—N1—C2—C8	168.99 (17)	O4—N2—C13—C12	−47.1 (3)
C1—N1—C2—C3	50.8 (2)	O5—N2—C13—C12	131.6 (2)
C1—N1—C2—C9	−71.6 (2)	O4—N2—C13—C14	134.3 (2)
N1—C2—C3—C4	−49.4 (2)	O5—N2—C13—C14	−47.1 (3)
C8—C2—C3—C4	−164.50 (19)	C12—C13—C14—C15	−1.2 (3)
C9—C2—C3—C4	73.1 (3)	N2—C13—C14—C15	177.42 (19)
C2—C3—C4—O1	−128.3 (2)	C12—C13—C14—Cl1	176.34 (15)
C2—C3—C4—C5	54.4 (3)	N2—C13—C14—Cl1	−5.0 (3)
O1—C4—C5—C1	129.6 (2)	C13—C14—C15—C10	−0.2 (3)
C3—C4—C5—C1	−53.1 (3)	Cl1—C14—C15—C10	−177.79 (16)
N1—C1—C5—C4	47.4 (2)	C11—C10—C15—C14	1.1 (3)
C7—C1—C5—C4	−75.6 (2)	C12—C11—C16—O3	−1.2 (3)
C6—C1—C5—C4	162.25 (19)	C10—C11—C16—O3	177.94 (19)
C15—C10—C11—C12	−0.7 (3)	C12—C11—C16—O2	179.46 (19)
C15—C10—C11—C16	−179.79 (18)	C10—C11—C16—O2	−1.4 (3)
C10—C11—C12—C13	−0.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.87 (2)	1.89 (2)	2.750 (2)	165
N1—H1B···O2ⁱⁱ	0.89 (1)	1.77 (1)	2.653 (2)	171
C3—H3A···O4ⁱⁱⁱ	0.97	2.54	3.269 (3)	132
C8—H8B···O3ⁱ	0.96	2.54	3.297 (3)	136

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

Experimental details

Crystal data
Chemical formula	C₉H₁₈NO⁺·C₇H₃ClNO₄⁻
M_r	356.80
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.9974 (10), 10.3267 (13), 11.9196 (15)
α, β, γ (°)	109.101 (3), 96.785 (3), 104.720 (3)
V (Å³)	877.58 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.40 × 0.14 × 0.09

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.908, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	10082, 3431, 2268
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.126, 1.01
No. of reflections	3431
No. of parameters	229
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.18

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.874 (16)	1.894 (16)	2.750 (2)	165
N1—H1B···O2ⁱⁱ	0.887 (12)	1.773 (13)	2.653 (2)	171
C3—H3A···O4ⁱⁱⁱ	0.97	2.54	3.269 (3)	132
C8—H8B···O3ⁱ	0.96	2.54	3.297 (3)	136

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

Acknowledgements

The authors thank the Malaysian Government, Universiti Kebangsaan Malaysia and the Ministry of Higher Education, Malaysia, for research grants UKM-GUP-NBT– 08–27–110.

References

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