1,1,3,3-Tetra­ethyl­isoindolin-2-ium chloride

Smith, G.; Wermuth, U.D.

doi:10.1107/S1600536812004588

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o659

doi:10.1107/S1600536812004588

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1,1,3,3-Tetraethylisoindolin-2-ium chloride

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

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

(Received 15 January 2012; accepted 2 February 2012; online 10 February 2012)

In the title compound, C₁₆H₂₆N⁺·Cl⁻, the cations and anions form discrete centrosymetric cyclic dimers through N—H⋯Cl hydrogen-bonding associations with graph-set R₄²(8).

Related literature

For the structures of related isoindoline and isoindolinium compounds, see: Fairhurst et al. (1996 ); Micallef et al. (1999 ). For the synthesis of alkyl-substituted isoindolines, see: Tönjes et al. (1964 ); Griffiths et al. (1983 ). For graph-set anlysis, see: Etter et al. (1990 ).

Experimental

Crystal data

C₁₆H₂₆N⁺·Cl⁻
M_r = 267.83
Orthorhombic, P b c a
a = 12.7282 (4) Å
b = 14.0676 (4) Å
c = 17.0771 (5) Å
V = 3057.74 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 200 K
0.45 × 0.12 × 0.08 mm

Data collection

Oxford Diffraction Gemini-S CCD diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.980, T_max = 0.990
9765 measured reflections
3007 independent reflections
2126 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.086
S = 0.91
3007 reflections
171 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1A⋯Cl1ⁱ	0.906 (18)	2.322 (18)	3.2054 (15)	165.0 (15)
N2—H1B⋯Cl1	0.915 (17)	2.306 (17)	3.1669 (14)	156.8 (14)
Symmetry code: (i) -x+1, -y, -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: 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: 10.1107/S1600536812004588/lh5407sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004588/lh5407Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812004588/lh5407Isup3.cml

checkCIF report

Comment top

The 1,1,3,3-tetraalkyl-substituted isoindolines have been useful intermediates for the synthesis of nitroxide free-radical scavengers (Griffiths et al., 1983). However, few structures of these compounds are found in the crystallographic literature, e.g. 5-nitro-1,1,3,3-tetramethylisoindoline (Fairhurst et al., 1996) and the salt hydrate 1,1,3,3-tetramethylisoindolinium bromide dihydrate (Micallef et al., 1999). The analogous anhydrous 1,1,3,3-tetraethyl-substituted salt C₁₆H₂₆N⁺ Cl^-, the title compound, has been synthesized and the structure is reported here.

The molecular structure of the title compound is shown in Fig. 1. The cations and the chloride anions form discrete centrosymetric cyclic dimers through N—H···Cl hydrogen-bonding associations [graph set R²₄(8) (Etter et al., 1990)] (Table 1, Fig. 2). The ethyl substituent groups of the molecule adopt various conformations [torsion angles N2—C1—C11—C12, 174.22 (14)°; N2—C1—C13—C14, -69.14 (18)°; N2—C3—C31—C32, 66.66 (17)°; N2—C3—C33—C34, 71.03 (18)°].

Related literature top

For the structures of related isoindoline and isoindolinium compounds, see: Fairhurst et al. (1996); Micallef et al. (1999). For the synthesis of alkyl-substituted isoindolines, see: Tönjes et al. (1964); Griffiths et al. (1983). For graph-set anlysis, see: Etter et al. (1990).

Experimental top

The title compound was synthesized using a modification of the method of Tönjes et al. (1964) for the synthesis of the 1,1,3,3-tetramethyl analogue (Griffiths et al., 1983). The modification involved the use of ethylmagnesium iodide in the reaction with N-benzylphthalimide followed by hydrogenation and conversion to the chloride salt. Colourless needles were obtained from a solution in glacial acetic acid and a specimen was cleaved for the X-ray analysis.

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. The molecular structure of title compound. The inter-species hydrogen bond is shown as a dashed line and displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. A perspective view of the hydrogen-bonded dimeric structure in the unit cell, showing the centrosymmetric cyclic R²₄(8) hydrogen-bonding motif. For symmetry code (i), see Table 1.

1,1,3,3-Tetraethylisoindolin-2-ium chloride top

Crystal data top

C₁₆H₂₆N⁺·Cl⁻	F(000) = 1168
M_r = 267.83	D_x = 1.164 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4071 reflections
a = 12.7282 (4) Å	θ = 3.2–28.8°
b = 14.0676 (4) Å	µ = 0.24 mm⁻¹
c = 17.0771 (5) Å	T = 200 K
V = 3057.74 (16) Å³	Needle, colourless
Z = 8	0.45 × 0.12 × 0.08 mm

Data collection top

Oxford Diffraction Gemini-S CCD diffractometer	3007 independent reflections
Radiation source: Enhance (Mo) X-ray source	2126 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 16.077 pixels mm^-1	θ_max = 26.0°, θ_min = 3.2°
ω scans	h = −14→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −17→16
T_min = 0.980, T_max = 0.990	l = −9→21
9765 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ²(F_o²) + (0.0507P)²] where P = (F_o² + 2F_c²)/3
3007 reflections	(Δ/σ)_max < 0.001
171 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₆H₂₆N⁺·Cl⁻	V = 3057.74 (16) Å³
M_r = 267.83	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.7282 (4) Å	µ = 0.24 mm⁻¹
b = 14.0676 (4) Å	T = 200 K
c = 17.0771 (5) Å	0.45 × 0.12 × 0.08 mm

Data collection top

Oxford Diffraction Gemini-S CCD diffractometer	3007 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2126 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.990	R_int = 0.028
9765 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	Δρ_max = 0.25 e Å⁻³
3007 reflections	Δρ_min = −0.15 e Å⁻³
171 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
N2	0.57440 (10)	0.11256 (10)	0.59705 (8)	0.0215 (4)
C1	0.53181 (12)	0.11091 (11)	0.68132 (9)	0.0231 (5)
C3	0.66601 (12)	0.18396 (10)	0.58973 (9)	0.0228 (5)
C4	0.71046 (12)	0.31935 (11)	0.68650 (9)	0.0265 (5)
C5	0.68541 (13)	0.36369 (11)	0.75667 (10)	0.0294 (5)
C6	0.60529 (13)	0.32973 (11)	0.80353 (9)	0.0281 (5)
C7	0.55023 (12)	0.24882 (11)	0.78244 (9)	0.0262 (5)
C8	0.57612 (12)	0.20269 (10)	0.71300 (9)	0.0213 (5)
C9	0.65433 (11)	0.23876 (10)	0.66514 (9)	0.0210 (5)
C11	0.58119 (13)	0.02388 (11)	0.72323 (9)	0.0296 (5)
C12	0.55776 (16)	0.01439 (14)	0.81002 (10)	0.0443 (7)
C13	0.41208 (12)	0.10409 (12)	0.68007 (10)	0.0306 (5)
C14	0.35314 (13)	0.19029 (12)	0.65082 (11)	0.0391 (6)
C31	0.65211 (13)	0.24731 (12)	0.51751 (9)	0.0313 (6)
C32	0.55947 (15)	0.31571 (13)	0.51940 (11)	0.0406 (6)
C33	0.77174 (12)	0.13089 (12)	0.58608 (11)	0.0338 (6)
C34	0.79401 (15)	0.07602 (14)	0.51062 (12)	0.0484 (7)
Cl1	0.41410 (3)	0.10600 (3)	0.45532 (2)	0.0300 (1)
H1A	0.5909 (13)	0.0523 (13)	0.5829 (11)	0.038 (5)*
H1B	0.5243 (13)	0.1283 (11)	0.5609 (10)	0.025 (4)*
H4	0.76350	0.34300	0.65460	0.0320*
H5	0.72310	0.41700	0.77240	0.0350*
H6	0.58820	0.36150	0.84960	0.0340*
H7	0.49670	0.22560	0.81420	0.0310*
H11A	0.55690	−0.03330	0.69710	0.0350*
H11B	0.65680	0.02690	0.71660	0.0350*
H12A	0.59160	−0.04150	0.83010	0.0660*
H12B	0.48330	0.00930	0.81770	0.0660*
H12C	0.58360	0.06940	0.83720	0.0660*
H13A	0.39270	0.05030	0.64760	0.0370*
H13B	0.38830	0.09050	0.73280	0.0370*
H14A	0.27900	0.17790	0.65230	0.0590*
H14B	0.37400	0.20390	0.59800	0.0590*
H14C	0.36890	0.24390	0.68360	0.0590*
H31A	0.71590	0.28410	0.51050	0.0370*
H31B	0.64460	0.20660	0.47200	0.0370*
H32A	0.55800	0.35200	0.47180	0.0610*
H32B	0.56670	0.35790	0.56320	0.0610*
H32C	0.49530	0.28030	0.52440	0.0610*
H33A	0.82770	0.17680	0.59370	0.0410*
H33B	0.77460	0.08650	0.62950	0.0410*
H34A	0.86140	0.04570	0.51440	0.0730*
H34B	0.79410	0.11920	0.46710	0.0730*
H34C	0.74060	0.02880	0.50300	0.0730*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0211 (7)	0.0257 (7)	0.0177 (7)	−0.0002 (6)	−0.0007 (6)	−0.0027 (6)
C1	0.0233 (8)	0.0279 (8)	0.0181 (8)	−0.0014 (7)	0.0032 (6)	−0.0008 (7)
C3	0.0205 (8)	0.0284 (8)	0.0196 (8)	−0.0049 (7)	0.0027 (6)	−0.0033 (7)
C4	0.0260 (9)	0.0310 (9)	0.0226 (9)	−0.0042 (7)	0.0025 (7)	0.0020 (7)
C5	0.0354 (10)	0.0260 (8)	0.0269 (9)	−0.0036 (7)	−0.0052 (7)	−0.0031 (7)
C6	0.0367 (10)	0.0283 (9)	0.0194 (8)	0.0081 (7)	−0.0007 (7)	−0.0042 (7)
C7	0.0277 (9)	0.0314 (9)	0.0195 (8)	0.0033 (7)	0.0047 (6)	0.0037 (7)
C8	0.0206 (8)	0.0250 (8)	0.0182 (8)	0.0022 (6)	−0.0002 (6)	0.0010 (7)
C9	0.0195 (8)	0.0262 (8)	0.0173 (8)	0.0028 (7)	−0.0007 (6)	−0.0006 (7)
C11	0.0345 (10)	0.0274 (9)	0.0269 (9)	0.0008 (8)	−0.0001 (8)	0.0027 (7)
C12	0.0594 (13)	0.0461 (11)	0.0274 (10)	0.0057 (10)	0.0009 (9)	0.0078 (9)
C13	0.0241 (8)	0.0378 (9)	0.0298 (9)	−0.0025 (8)	0.0038 (7)	0.0009 (8)
C14	0.0277 (10)	0.0511 (11)	0.0384 (11)	0.0086 (9)	0.0028 (8)	−0.0024 (9)
C31	0.0369 (10)	0.0400 (10)	0.0169 (9)	−0.0107 (8)	0.0024 (7)	−0.0002 (8)
C32	0.0508 (12)	0.0372 (10)	0.0338 (10)	−0.0044 (9)	−0.0092 (8)	0.0118 (9)
C33	0.0225 (9)	0.0419 (10)	0.0370 (11)	−0.0001 (8)	0.0066 (7)	−0.0069 (8)
C34	0.0368 (11)	0.0508 (12)	0.0576 (14)	−0.0053 (9)	0.0198 (10)	−0.0192 (11)
Cl1	0.0298 (2)	0.0341 (2)	0.0260 (2)	0.0029 (2)	−0.0059 (2)	−0.0047 (2)

Geometric parameters (Å, º) top

N2—C1	1.538 (2)	C6—H6	0.9300
N2—C3	1.544 (2)	C7—H7	0.9300
N2—H1A	0.906 (18)	C11—H11A	0.9700
N2—H1B	0.915 (17)	C11—H11B	0.9700
C1—C8	1.509 (2)	C12—H12A	0.9600
C1—C13	1.527 (2)	C12—H12B	0.9600
C1—C11	1.551 (2)	C12—H12C	0.9600
C3—C31	1.532 (2)	C13—H13A	0.9700
C3—C33	1.540 (2)	C13—H13B	0.9700
C3—C9	1.508 (2)	C14—H14A	0.9600
C4—C5	1.388 (2)	C14—H14B	0.9600
C4—C9	1.389 (2)	C14—H14C	0.9600
C5—C6	1.382 (2)	C31—H31A	0.9700
C6—C7	1.384 (2)	C31—H31B	0.9700
C7—C8	1.391 (2)	C32—H32A	0.9600
C8—C9	1.384 (2)	C32—H32B	0.9600
C11—C12	1.518 (2)	C32—H32C	0.9600
C13—C14	1.511 (2)	C33—H33A	0.9700
C31—C32	1.522 (3)	C33—H33B	0.9700
C33—C34	1.529 (3)	C34—H34A	0.9600
C4—H4	0.9300	C34—H34B	0.9600
C5—H5	0.9300	C34—H34C	0.9600

C1—N2—C3	110.59 (12)	C12—C11—H11A	108.00
H1A—N2—H1B	102.0 (15)	C12—C11—H11B	108.00
C1—N2—H1A	108.5 (12)	H11A—C11—H11B	107.00
C1—N2—H1B	112.9 (11)	C11—C12—H12A	109.00
C3—N2—H1A	114.3 (11)	C11—C12—H12B	110.00
C3—N2—H1B	108.3 (10)	C11—C12—H12C	109.00
N2—C1—C13	109.85 (12)	H12A—C12—H12B	109.00
C8—C1—C11	111.00 (12)	H12A—C12—H12C	109.00
N2—C1—C11	107.51 (12)	H12B—C12—H12C	109.00
N2—C1—C8	101.00 (12)	C1—C13—H13A	108.00
C11—C1—C13	111.17 (13)	C1—C13—H13B	108.00
C8—C1—C13	115.57 (13)	C14—C13—H13A	108.00
C9—C3—C33	111.62 (13)	C14—C13—H13B	108.00
C9—C3—C31	112.25 (12)	H13A—C13—H13B	107.00
N2—C3—C9	100.89 (12)	C13—C14—H14A	109.00
N2—C3—C31	110.88 (12)	C13—C14—H14B	109.00
N2—C3—C33	110.35 (12)	C13—C14—H14C	110.00
C31—C3—C33	110.51 (13)	H14A—C14—H14B	109.00
C5—C4—C9	118.39 (14)	H14A—C14—H14C	109.00
C4—C5—C6	120.95 (15)	H14B—C14—H14C	109.00
C5—C6—C7	120.49 (14)	C3—C31—H31A	108.00
C6—C7—C8	119.03 (14)	C3—C31—H31B	108.00
C1—C8—C9	111.76 (13)	C32—C31—H31A	108.00
C7—C8—C9	120.17 (14)	C32—C31—H31B	108.00
C1—C8—C7	128.03 (14)	H31A—C31—H31B	107.00
C3—C9—C8	112.81 (13)	C31—C32—H32A	109.00
C4—C9—C8	120.94 (14)	C31—C32—H32B	109.00
C3—C9—C4	126.21 (13)	C31—C32—H32C	109.00
C1—C11—C12	116.13 (14)	H32A—C32—H32B	109.00
C1—C13—C14	116.72 (14)	H32A—C32—H32C	110.00
C3—C31—C32	116.11 (14)	H32B—C32—H32C	109.00
C3—C33—C34	116.16 (14)	C3—C33—H33A	108.00
C5—C4—H4	121.00	C3—C33—H33B	108.00
C9—C4—H4	121.00	C34—C33—H33A	108.00
C4—C5—H5	120.00	C34—C33—H33B	108.00
C6—C5—H5	119.00	H33A—C33—H33B	107.00
C5—C6—H6	120.00	C33—C34—H34A	109.00
C7—C6—H6	120.00	C33—C34—H34B	109.00
C6—C7—H7	121.00	C33—C34—H34C	109.00
C8—C7—H7	120.00	H34A—C34—H34B	109.00
C1—C11—H11A	108.00	H34A—C34—H34C	110.00
C1—C11—H11B	108.00	H34B—C34—H34C	110.00

C3—N2—C1—C8	17.41 (15)	C31—C3—C9—C8	122.53 (14)
C3—N2—C1—C11	−98.96 (14)	C33—C3—C9—C4	69.65 (19)
C3—N2—C1—C13	139.94 (13)	C33—C3—C9—C8	−112.77 (15)
C1—N2—C3—C33	104.26 (14)	N2—C3—C31—C32	66.66 (17)
C1—N2—C3—C9	−13.87 (15)	C9—C3—C31—C32	−45.33 (19)
C1—N2—C3—C31	−132.96 (13)	C33—C3—C31—C32	−170.65 (14)
N2—C1—C8—C9	−14.63 (16)	N2—C3—C33—C34	71.03 (18)
C13—C1—C8—C7	49.6 (2)	C9—C3—C33—C34	−177.64 (14)
C11—C1—C8—C7	−78.24 (19)	C31—C3—C33—C34	−51.97 (18)
C11—C1—C8—C9	99.12 (15)	C9—C4—C5—C6	−1.2 (2)
N2—C1—C8—C7	168.01 (15)	C5—C4—C9—C3	176.62 (14)
C13—C1—C11—C12	−65.51 (18)	C5—C4—C9—C8	−0.8 (2)
N2—C1—C13—C14	−69.14 (18)	C4—C5—C6—C7	1.9 (2)
C8—C1—C13—C14	44.3 (2)	C5—C6—C7—C8	−0.6 (2)
C11—C1—C13—C14	171.99 (14)	C6—C7—C8—C1	175.77 (15)
C13—C1—C8—C9	−133.09 (14)	C6—C7—C8—C9	−1.4 (2)
N2—C1—C11—C12	174.22 (14)	C1—C8—C9—C3	6.78 (18)
C8—C1—C11—C12	64.62 (18)	C1—C8—C9—C4	−175.50 (14)
N2—C3—C9—C4	−173.14 (14)	C7—C8—C9—C3	−175.63 (13)
N2—C3—C9—C8	4.44 (16)	C7—C8—C9—C4	2.1 (2)
C31—C3—C9—C4	−55.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1A···Cl1ⁱ	0.906 (18)	2.322 (18)	3.2054 (15)	165.0 (15)
N2—H1B···Cl1	0.915 (17)	2.306 (17)	3.1669 (14)	156.8 (14)
C4—H4···Cl1ⁱⁱ	0.93	2.78	3.6995 (16)	172
C11—H11A···Cl1ⁱ	0.97	2.82	3.5551 (16)	133
C34—H34C···Cl1ⁱ	0.96	2.82	3.730 (2)	158

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

Experimental details

Crystal data
Chemical formula	C₁₆H₂₆N⁺·Cl⁻
M_r	267.83
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	200
a, b, c (Å)	12.7282 (4), 14.0676 (4), 17.0771 (5)
V (Å³)	3057.74 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.45 × 0.12 × 0.08

Data collection
Diffractometer	Oxford Diffraction Gemini-S CCD diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.980, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	9765, 3007, 2126
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.086, 0.91
No. of reflections	3007
No. of parameters	171
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.15

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
N2—H1A···Cl1ⁱ	0.906 (18)	2.322 (18)	3.2054 (15)	165.0 (15)
N2—H1B···Cl1	0.915 (17)	2.306 (17)	3.1669 (14)	156.8 (14)

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

The authors acknowledge financial support from the Australian Research Council, and the Science and Engineering Faculty and the University Library, Queensland University of Technology.

References

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