4-Chloro­anilinium 2-carb­oxy-4,5-dichloro­benzoate

Smith, G.; Wermuth, U.D.; White, J.M.

doi:10.1107/S160053680903044X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2111

doi:10.1107/S160053680903044X

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4-Chloroanilinium 2-carboxy-4,5-dichlorobenzoate

Graham Smith,^a ^* Urs D. Wermuth ^a and Jonathan M. White ^b

^aSchool of Physical and Chemical Sciences, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia, and ^bBIO-21 Molecular Science and Biotechnology, University of Melbourne, Parkville, Victoria 3052, Australia
^*Correspondence e-mail: g.smith@qut.edu.au

(Received 14 July 2009; accepted 31 July 2009; online 8 August 2009)

The structure of the 1:1 proton-transfer compound of 4-chloroaniline with 4,5-dichlorophthalic acid (DCPA), viz. C₆H₇ClN⁺·C₈H₃Cl₂O₄⁻, has been determined at 130 K. The non-planar hydrogen phthalate anions and the 4-chloroanilinium cations form two-dimensional O—H⋯O and N—H⋯O hydrogen-bonded substructures which have no peripheral extension. Between the sheets there are weak π–π associations between alternating cation–anion aromatic ring systems [shortest centroid–centroid separation = 3.735 (4) Å].

Related literature

For the structures of other hydrogen DCPA salts with aromatic Lewis bases showing similar two-dimensional substructures, see: Smith et al. (2008b ). This contrasts with the majority of the compounds in which the DCPA anion is planar with a short intramolecular carboxylic acid hydrogen bond, see: Smith et al. (2007 , 2008a , 2009 ).

Experimental

Crystal data

C₆H₇ClN⁺·C₈H₃Cl₂O₄⁻
M_r = 362.58
Monoclinic, C 2
a = 12.8171 (8) Å
b = 7.5954 (3) Å
c = 16.0909 (6) Å
β = 109.815 (5)°
V = 1473.72 (13) Å³
Z = 4
Cu Kα radiation
μ = 5.80 mm⁻¹
T = 130 K
0.34 × 0.27 × 0.05 mm

Data collection

Oxford Diffraction Gemini Ultra CCD-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.201, T_max = 0.748
3680 measured reflections
2288 independent reflections
1879 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.175
S = 1.00
2288 reflections
215 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.56 e Å⁻³
Absolute structure: Flack (1983 ), 723 Friedel pairs
Flack parameter: 0.04 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O12—H12⋯O21ⁱ	0.81 (3)	1.69 (3)	2.485 (5)	166 (4)
N1A—H11A⋯O11ⁱⁱ	0.89 (4)	2.03 (4)	2.867 (8)	157 (4)
N1A—H11A⋯O22	0.89 (4)	2.59 (4)	2.875 (7)	100 (2)
N1A—H12A⋯O22	0.88 (3)	2.58 (5)	2.875 (7)	100 (3)
N1A—H12A⋯O22ⁱⁱⁱ	0.88 (3)	1.94 (3)	2.813 (6)	172 (5)
N1A—H13A⋯O12^iv	0.88 (4)	2.58 (5)	3.019 (7)	112 (3)
N1A—H13A⋯O21^iv	0.88 (4)	1.94 (4)	2.805 (7)	166 (4)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+2]$ ; (ii) x, y+1, z; (iii) -x+1, y, -z+2; (iv) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); 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/S160053680903044X/at2844sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680903044X/at2844Isup2.hkl

checkCIF report

Comment top

Among the known structures of the 1:1 aromatic Lewis base compounds of 4,5-dichlorophthalic acid (DCPA), a small number have similar hydrogen-bonded substructures in which the basic N⁺—H···O_carboxyl linked cation–anion unit is propagated in two dimensions (Smith et al., 2008b). In these the DCPA anions are non-planar with the carboxylic acid and carboxylate groups rotated out of the plane of the benzene ring. This contrasts with the majority of the compounds in which the DCPA anion is planar with a short intramolecular carboxylic acid O–H···O_carboxyl hydrogen bond (Smith et al., 2007, 2008a, 2009). Since the examples having the two-dimensional substructures were substituted anilines, the 4-chloro-analogue was reacted with DCPA, giving anhydrous 4-chloroanilinium 2-carboxy-4,5-dichlorobenzoate C₆H₇ClN⁺. C₈H₃Cl₂O₄^- (I) and its structure is reported here.

In (I), as expected, the primary hydrogen-bonded cation–anion structural unit (Fig.1) provides the basis for formation of the previously described two-dimensional substructure which extends across the ab plane in the unit cell, having no lateral interactions (Fig. 2). The hydrogen bonding within the plane (Table 1) includes a cyclic R²₁(6) anilinium–H···O12,O21 interaction. The alternating cation–anion aromatic ring systems (C1–C6 and C1A–C6A) give weak π–π interactions [shortest centroid separation 3.735 (4) Å]. The hydrogen 4,5-dichlorophthalate anion is non-planar [torsion angles C2–C1–C11–O11, 163.7 (7)°: C1–C2–C21–O22, -83.3 (8)°].,

Related literature top

For the structures of other hydrogen DCPA salts with aromatic Lewis bases showing similar two-dimensional substructures, see: Smith et al. (2008b). This contrasts with the majority of the compounds in which the DCPA anion is planar with a short intramolecular carboxylic acid hydrogen bond, see: Smith et al. (2007, 2008a, 2009).

Experimental top

The title compound (I) was synthesized by heating together 1 mmol quantities of 4-chloroaniline and 4,5-dichlorophthalic acid in 50 ml of 50% aqueous methanol for 10 min under reflux. After concentration to ca. 30 ml, partial room-temperature evaporation of the hot-filtered solution gave small colourless plates [m.p. 492 K]).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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 numbering scheme for the 4-chloroanilinium cation and the hydrogen 4,5-dichlorophthalate anion in (I). Non-H atoms are shown as 50% probability displacement ellipsoids. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The two-dimensional sheet structure in (I) viewed down the b axis in the unit cell. Non-interactive H atoms are omitted and hydrogen bonds are shown as dashed lines. (For symmetry codes, see Table 1).

4-Chloroanilinium 2-carboxy-4,5-dichlorobenzoate top

Crystal data top

C₆H₇ClN⁺·C₈H₃Cl₂O₄⁻	F(000) = 736
M_r = 362.58	D_x = 1.634 Mg m⁻³
Monoclinic, C2	Melting point: 492 K
Hall symbol: C 2y	Cu Kα radiation, λ = 1.54184 Å
a = 12.8171 (8) Å	Cell parameters from 1721 reflections
b = 7.5954 (3) Å	θ = 2.9–71.8°
c = 16.0909 (6) Å	µ = 5.80 mm⁻¹
β = 109.815 (5)°	T = 130 K
V = 1473.72 (13) Å³	Plate, colourless
Z = 4	0.34 × 0.27 × 0.05 mm

Data collection top

Oxford Diffraction Gemini Ultra CCD-detector diffractometer	2288 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray source	1879 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.061
ω scans	θ_max = 72.1°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→14
T_min = 0.201, T_max = 0.748	k = −9→8
3680 measured reflections	l = −15→19

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)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.175	w = 1/[σ²(F_o²) + (0.135P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2288 reflections	Δρ_max = 0.64 e Å⁻³
215 parameters	Δρ_min = −0.56 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 723 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (3)

Crystal data top

C₆H₇ClN⁺·C₈H₃Cl₂O₄⁻	V = 1473.72 (13) Å³
M_r = 362.58	Z = 4
Monoclinic, C2	Cu Kα radiation
a = 12.8171 (8) Å	µ = 5.80 mm⁻¹
b = 7.5954 (3) Å	T = 130 K
c = 16.0909 (6) Å	0.34 × 0.27 × 0.05 mm
β = 109.815 (5)°

Data collection top

Oxford Diffraction Gemini Ultra CCD-detector diffractometer	2288 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1879 reflections with I > 2σ(I)
T_min = 0.201, T_max = 0.748	R_int = 0.061
3680 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.175	Δρ_max = 0.64 e Å⁻³
S = 1.00	Δρ_min = −0.56 e Å⁻³
2288 reflections	Absolute structure: Flack (1983), 723 Friedel pairs
215 parameters	Absolute structure parameter: 0.04 (3)
1 restraint

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
Cl4	0.39571 (14)	0.8094 (3)	0.55613 (9)	0.0377 (5)
Cl5	0.37318 (14)	0.3980 (3)	0.58289 (9)	0.0418 (5)
O11	0.5642 (4)	0.3295 (7)	0.9286 (3)	0.0348 (14)
O12	0.6750 (3)	0.5632 (6)	0.9688 (2)	0.0282 (11)
O21	0.7198 (3)	0.9010 (6)	0.8943 (2)	0.0243 (10)
O22	0.5704 (3)	0.9285 (6)	0.9364 (2)	0.0272 (13)
C1	0.5441 (5)	0.5652 (8)	0.8257 (4)	0.0244 (16)
C2	0.5583 (5)	0.7457 (8)	0.8141 (3)	0.0222 (16)
C3	0.5118 (5)	0.8181 (9)	0.7299 (4)	0.0257 (16)
C4	0.4522 (5)	0.7126 (9)	0.6581 (4)	0.0289 (18)
C5	0.4402 (5)	0.5333 (9)	0.6707 (4)	0.0311 (18)
C6	0.4861 (5)	0.4599 (9)	0.7537 (4)	0.0276 (17)
C11	0.5956 (5)	0.4739 (9)	0.9139 (4)	0.0244 (17)
C21	0.6212 (4)	0.8673 (7)	0.8897 (3)	0.0237 (16)
Cl4A	0.13666 (14)	0.6564 (2)	0.60330 (9)	0.0387 (5)
N1A	0.3688 (4)	1.1240 (7)	0.9059 (3)	0.0234 (14)
C1A	0.3149 (5)	1.0096 (8)	0.8304 (3)	0.0233 (16)
C2A	0.2717 (5)	1.0813 (9)	0.7460 (4)	0.0292 (17)
C3A	0.2162 (5)	0.9729 (9)	0.6753 (4)	0.0300 (18)
C4A	0.2064 (5)	0.7965 (9)	0.6903 (4)	0.0286 (17)
C5A	0.2510 (5)	0.7210 (9)	0.7743 (4)	0.0283 (17)
C6A	0.3054 (5)	0.8316 (9)	0.8443 (3)	0.0263 (18)
H3	0.52050	0.93760	0.72140	0.0310*
H6	0.47830	0.34000	0.76170	0.0340*
H12	0.700 (3)	0.509 (4)	1.015 (2)	0.042 (11)*
H2A	0.27990	1.20080	0.73710	0.0340*
H3A	0.18610	1.01900	0.61860	0.0360*
H5A	0.24450	0.60100	0.78290	0.0340*
H6A	0.33560	0.78560	0.90100	0.0320*
H11A	0.425 (3)	1.179 (4)	0.897 (3)	0.035 (10)*
H12A	0.393 (4)	1.059 (3)	0.954 (2)	0.041 (11)*
H13A	0.320 (4)	1.202 (4)	0.910 (3)	0.038 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl4	0.0444 (9)	0.0546 (10)	0.0141 (6)	−0.0005 (8)	0.0035 (5)	0.0056 (6)
Cl5	0.0482 (10)	0.0479 (10)	0.0206 (6)	−0.0014 (8)	0.0002 (6)	−0.0120 (6)
O11	0.038 (2)	0.035 (3)	0.026 (2)	−0.011 (2)	0.0037 (17)	0.0002 (19)
O12	0.031 (2)	0.034 (2)	0.0147 (17)	0.0000 (18)	0.0015 (15)	0.0039 (16)
O21	0.0266 (18)	0.031 (2)	0.0155 (15)	−0.0022 (18)	0.0075 (14)	−0.0015 (15)
O22	0.026 (2)	0.033 (3)	0.0203 (17)	0.0019 (17)	0.0050 (15)	−0.0038 (16)
C1	0.028 (3)	0.027 (3)	0.017 (2)	0.001 (2)	0.006 (2)	−0.004 (2)
C2	0.023 (3)	0.029 (3)	0.015 (2)	−0.001 (2)	0.007 (2)	−0.001 (2)
C3	0.028 (3)	0.029 (3)	0.020 (2)	0.001 (3)	0.008 (2)	−0.001 (2)
C4	0.029 (3)	0.043 (4)	0.011 (2)	0.002 (3)	0.002 (2)	0.000 (2)
C5	0.030 (3)	0.041 (4)	0.017 (2)	−0.005 (3)	0.001 (2)	−0.006 (3)
C6	0.030 (3)	0.031 (3)	0.024 (3)	−0.003 (3)	0.012 (2)	−0.002 (2)
C11	0.022 (3)	0.033 (3)	0.019 (3)	−0.003 (2)	0.008 (2)	−0.001 (2)
C21	0.023 (3)	0.030 (3)	0.018 (2)	−0.002 (2)	0.007 (2)	−0.001 (2)
Cl4A	0.0489 (9)	0.0436 (10)	0.0201 (6)	−0.0072 (8)	0.0073 (6)	−0.0054 (6)
N1A	0.023 (2)	0.030 (3)	0.016 (2)	0.001 (2)	0.0050 (16)	0.0040 (19)
C1A	0.024 (3)	0.029 (3)	0.017 (2)	−0.004 (2)	0.007 (2)	−0.003 (2)
C2A	0.036 (3)	0.029 (3)	0.020 (3)	0.005 (3)	0.006 (2)	0.001 (2)
C3A	0.034 (3)	0.039 (4)	0.016 (2)	0.000 (3)	0.007 (2)	0.001 (2)
C4A	0.035 (3)	0.029 (3)	0.022 (3)	0.003 (3)	0.010 (2)	0.000 (2)
C5A	0.032 (3)	0.031 (3)	0.021 (3)	−0.002 (3)	0.008 (2)	0.002 (2)
C6A	0.029 (3)	0.032 (4)	0.018 (2)	0.000 (3)	0.008 (2)	0.002 (2)

Geometric parameters (Å, º) top

Cl4—C4	1.718 (6)	C2—C3	1.395 (8)
Cl5—C5	1.723 (7)	C3—C4	1.401 (9)
Cl4A—C4A	1.744 (7)	C4—C5	1.393 (10)
O11—C11	1.219 (9)	C5—C6	1.381 (9)
O12—C11	1.291 (8)	C3—H3	0.9300
O21—C21	1.267 (7)	C6—H6	0.9300
O22—C21	1.240 (6)	C1A—C6A	1.383 (9)
O12—H12	0.81 (3)	C1A—C2A	1.392 (8)
N1A—C1A	1.463 (7)	C2A—C3A	1.389 (9)
N1A—H13A	0.89 (4)	C3A—C4A	1.375 (10)
N1A—H12A	0.88 (3)	C4A—C5A	1.400 (9)
N1A—H11A	0.88 (4)	C5A—C6A	1.389 (8)
C1—C2	1.404 (9)	C2A—H2A	0.9300
C1—C11	1.515 (9)	C3A—H3A	0.9300
C1—C6	1.397 (9)	C5A—H5A	0.9300
C2—C21	1.523 (7)	C6A—H6A	0.9300

C11—O12—H12	110 (2)	O22—C21—C2	117.9 (5)
H11A—N1A—H12A	110 (4)	O21—C21—C2	114.6 (5)
H11A—N1A—H13A	109 (4)	C2—C3—H3	120.00
C1A—N1A—H13A	108 (3)	C4—C3—H3	120.00
C1A—N1A—H11A	109 (3)	C5—C6—H6	120.00
H12A—N1A—H13A	111 (4)	C1—C6—H6	120.00
C6—C1—C11	117.1 (6)	C2A—C1A—C6A	120.9 (5)
C2—C1—C11	122.5 (5)	N1A—C1A—C6A	119.3 (4)
C2—C1—C6	120.4 (5)	N1A—C1A—C2A	119.8 (5)
C1—C2—C3	118.8 (5)	C1A—C2A—C3A	119.4 (6)
C3—C2—C21	118.2 (5)	C2A—C3A—C4A	119.1 (6)
C1—C2—C21	122.9 (5)	Cl4A—C4A—C3A	120.4 (5)
C2—C3—C4	120.6 (6)	Cl4A—C4A—C5A	117.1 (5)
C3—C4—C5	119.7 (6)	C3A—C4A—C5A	122.5 (6)
Cl4—C4—C5	121.7 (5)	C4A—C5A—C6A	117.6 (6)
Cl4—C4—C3	118.6 (5)	C1A—C6A—C5A	120.5 (5)
Cl5—C5—C6	118.9 (5)	C1A—C2A—H2A	120.00
C4—C5—C6	120.2 (6)	C3A—C2A—H2A	120.00
Cl5—C5—C4	120.9 (5)	C2A—C3A—H3A	120.00
C1—C6—C5	120.2 (6)	C4A—C3A—H3A	120.00
O11—C11—C1	121.7 (6)	C4A—C5A—H5A	121.00
O11—C11—O12	125.1 (6)	C6A—C5A—H5A	121.00
O12—C11—C1	113.1 (6)	C1A—C6A—H6A	120.00
O21—C21—O22	127.4 (5)	C5A—C6A—H6A	120.00

C6—C1—C2—C3	1.2 (10)	C2—C3—C4—C5	−0.7 (10)
C6—C1—C2—C21	−179.6 (6)	Cl4—C4—C5—Cl5	3.1 (9)
C11—C1—C2—C3	177.4 (6)	Cl4—C4—C5—C6	−179.6 (5)
C11—C1—C2—C21	−3.4 (10)	C3—C4—C5—Cl5	−176.9 (5)
C2—C1—C6—C5	−1.4 (10)	C3—C4—C5—C6	0.5 (10)
C11—C1—C6—C5	−177.8 (6)	Cl5—C5—C6—C1	177.9 (5)
C2—C1—C11—O11	163.7 (7)	C4—C5—C6—C1	0.5 (10)
C2—C1—C11—O12	−17.4 (9)	N1A—C1A—C2A—C3A	−177.1 (6)
C6—C1—C11—O11	−20.0 (10)	C6A—C1A—C2A—C3A	1.5 (10)
C6—C1—C11—O12	159.0 (6)	N1A—C1A—C6A—C5A	177.6 (6)
C1—C2—C3—C4	−0.2 (10)	C2A—C1A—C6A—C5A	−0.9 (10)
C21—C2—C3—C4	−179.4 (6)	C1A—C2A—C3A—C4A	−0.8 (10)
C1—C2—C21—O21	100.2 (7)	C2A—C3A—C4A—Cl4A	179.7 (5)
C1—C2—C21—O22	−83.3 (8)	C2A—C3A—C4A—C5A	−0.5 (10)
C3—C2—C21—O21	−80.6 (7)	Cl4A—C4A—C5A—C6A	−179.1 (5)
C3—C2—C21—O22	95.9 (7)	C3A—C4A—C5A—C6A	1.0 (10)
C2—C3—C4—Cl4	179.4 (5)	C4A—C5A—C6A—C1A	−0.3 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···O21ⁱ	0.81 (3)	1.69 (3)	2.485 (5)	166 (4)
N1A—H11A···O11ⁱⁱ	0.89 (4)	2.03 (4)	2.867 (8)	157 (4)
N1A—H11A···O22	0.89 (4)	2.59 (4)	2.875 (7)	100 (2)
N1A—H12A···O22	0.88 (3)	2.58 (5)	2.875 (7)	100 (3)
N1A—H12A···O22ⁱⁱⁱ	0.88 (3)	1.94 (3)	2.813 (6)	172 (5)
N1A—H13A···O12^iv	0.88 (4)	2.58 (5)	3.019 (7)	112 (3)
N1A—H13A···O21^iv	0.88 (4)	1.94 (4)	2.805 (7)	166 (4)
C5A—H5A···O21^v	0.93	2.45	3.212 (8)	139

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

Experimental details

Crystal data
Chemical formula	C₆H₇ClN⁺·C₈H₃Cl₂O₄⁻
M_r	362.58
Crystal system, space group	Monoclinic, C2
Temperature (K)	130
a, b, c (Å)	12.8171 (8), 7.5954 (3), 16.0909 (6)
β (°)	109.815 (5)
V (Å³)	1473.72 (13)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	5.80
Crystal size (mm)	0.34 × 0.27 × 0.05

Data collection
Diffractometer	Oxford Diffraction Gemini Ultra CCD-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.201, 0.748
No. of measured, independent and observed [I > 2σ(I)] reflections	3680, 2288, 1879
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.175, 1.00
No. of reflections	2288
No. of parameters	215
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.56
Absolute structure	Flack (1983), 723 Friedel pairs
Absolute structure parameter	0.04 (3)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···O21ⁱ	0.81 (3)	1.69 (3)	2.485 (5)	166 (4)
N1A—H11A···O11ⁱⁱ	0.89 (4)	2.03 (4)	2.867 (8)	157 (4)
N1A—H11A···O22	0.89 (4)	2.59 (4)	2.875 (7)	100 (2)
N1A—H12A···O22	0.88 (3)	2.58 (5)	2.875 (7)	100 (3)
N1A—H12A···O22ⁱⁱⁱ	0.88 (3)	1.94 (3)	2.813 (6)	172 (5)
N1A—H13A···O12^iv	0.88 (4)	2.58 (5)	3.019 (7)	112 (3)
N1A—H13A···O21^iv	0.88 (4)	1.94 (4)	2.805 (7)	166 (4)

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

Acknowledgements

The authors acknowledge financial support from the School of Physical and Chemical Sciences (Queensland University of Technology) and the School of Chemistry, the University of Melbourne.

References

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