Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 10| October 2013| Page o1546
doi:10.1107/S1600536813025014

4-Meth­­oxy­anilinium 2-carb­­oxy-4,5-di­chloro­benzoate

Graham Smitha* and Urs D. Wermutha

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

(Received 8 September 2013; accepted 9 September 2013; online 18 September 2013)

In the title salt C7H10NO+·C8H3Cl2O4− the benzene rings of the cation and anion are essentially parallel [inter-ring dihedral angle 4.8 (2)°]. In the anion the carb­oxy­lic acid and carboxyl­ate groups make dihedral angles of 19.0 (2) and 79.5 (2)°, respectively, with the benzene ring. Aminium N—H⋯O, carb­oxy­lic acid O—H⋯O and weak aromatic C—H⋯O hydrogen-bonding associations with carboxyl O-atom acceptors together with cation–anion π–π ring inter­actions [minimum ring centroid separation = 3.734 (3) Å] give rise to a sheet structure lying parallel to (001).

CCDC reference: 960147

Related literature

For background to 4,5-di­chloro­phthalate salts, see: Mattes & Dorau (1986[Mattes, R. & Dorau, A. (1986). Z. Naturforsch. Chem. Sci. 41, 808-814.]); Smith et al. (2008a[Smith, G., Wermuth, U. D. & White, J. M. (2008a). Acta Cryst. C64, o180-o183.]). For structures of some 1:1 anilinium salts of 4,5-di­chloro­phthalic acid, see: Odabaşoğlu & Büyükgüngör (2007[Odabaşoğlu, M. & Büyükgüngör, O. (2007). Acta Cryst. E63, o4374-o4375.]); Smith et al. (2008b[Smith, G., Wermuth, U. D. & White, J. M. (2008b). Acta Cryst. C64, o532-o536.]); Smith et al. (2009[Smith, G., Wermuth, U. D. & White, J. M. (2009). Acta Cryst. E65, o2111.]). For the structure of a dianionic 4,5-di­chloro­phthalate salt, see: Smith & Wermuth (2012[Smith, G. & Wermuth, U. D. (2012). Acta Cryst. E68, o1928.]).

[Scheme 1]

Experimental

Crystal data

  • C7H10NO+·C8H3Cl2O4−

  • Mr = 358.16

  • Orthorhombic, C 2221

  • a = 7.5319 (8) Å

  • b = 12.9302 (14) Å

  • c = 32.3268 (18) Å

  • V = 3148.3 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.44 mm−1

  • T = 200 K

  • 0.35 × 0.30 × 0.15 mm
Data collection

  • Oxford Diffraction Gemini-S CCD-detector diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO, Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.759, Tmax = 0.980

  • 6518 measured reflections

  • 2730 independent reflections

  • 2620 reflections with I > 2σ(I)

  • Rint = 0.036
Refinement

  • R[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 0.117

  • S = 1.42

  • 2730 reflections

  • 208 parameters

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.33 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1569 Friedel pairs

  • Absolute structure parameter: 0.03 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1A—H11A⋯O22i 0.81 2.10 2.881 (5) 163
N1A—H12A⋯O11ii 0.87 1.95 2.811 (5) 168
N1A—H13A⋯O12 0.99 1.84 2.814 (5) 167
O21—H21⋯O12ii 0.95 1.53 2.480 (4) 179
C3A—H3A⋯O12iii 0.95 2.50 3.265 (7) 137
Symmetry codes: (i) [x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (iii) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) within ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information

CCDC reference: 960147

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813025014/sj5350sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813025014/sj5350Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813025014/sj5350Isup3.cml

checkCIF report


Comment top

4,5-Dichlorophthalic acid (DCPA) most commonly forms 1:1 salts with organic Lewis bases, often giving low-dimensional hydrogen-bonded structures (Mattes & Dorau, 1986; Smith et al., 2008a). The 1:2 DCPA salts are uncommon, as is the presence of water molecules of solvation, an example being the benzylamine salt (a monohydrate) (Smith & Wermuth, 2012). The salts with the aniline analogues are also not common, e.g. with 3-(trifluoromethyl)aniline (Odabaşoğlu & Büyükgüngör, 2007), the three isomeric carboxylanilines (Smith et al., 2008b and 2-chloroaniline (Smith et al., 2009). Our 1:1 stoichiometric reaction of DCPA with 4-methoxyaniline (p-anisidine) gave the anhydrous 1:1 salt C7H10NO+ C8H3Cl2O4-, the title compound, and the structure is reported herein.

In this structure (Fig. 1), the DCPA anion does not have the 'planar' conformation which is found in a large number of the 1:1 structures, but has the carboxylic acid and carboxylate groups rotated out of the benzene plane forming dihedral angles of 19.0 (2)° and 79.5 (2)°, respectively, with it. These correspond to torsion angles C1—C2—C21—O21 and C2—C1—C11—O11 of 19.1 (6) and 81.2 (5)°. In the crystal the cation and anion rings are close to parallel [inter-ring dihedral angle = 4.8 (2)°], giving layering along b. Weak π–π interactions are present between the benzene rings of the cations and anions [minimum ring centroid separation Cg···Cgiv = 3.734 (3) Å] [for symmetry code (iv): x + 1/2, y + 1/2, z]. Aminium N—H···O, water O—H···O and weak aromatic C—H···O hydrogen-bonding associations with carboxyl O-atom acceptors (Table 1) give a two-dimensional sheet structure which lies parallel to (001) (Fig. 2).

Related literature top

For background to 4,5-dichlorophthalate salts, see: Mattes & Dorau (1986); Smith et al. (2008a). For structures of some 1:1 anilinium salts of 4,5-dichlorophthalic acid, see: Odabaşoğlu & Büyükgüngör (2007); Smith et al. (2008b); Smith et al. (2009). For the structure of a dianionic 4,5-dichlorophthalate salt, see: Smith & Wermuth (2012).

Experimental top

The title compound was synthesized by heating together for 10 min under reflux, 1 mmol quantities of 4,5-dichlorophthalic acid and 4-methoxyaniline (p-anisidine) in 50 ml of methanol. Partial evaporation of the solvent gave large colourless crystalline plates of the title compound (m.p. 473 K) from which a specimen was cleaved for the X-ray analysis..

Refinement top

The aminium and carboxylic acid hydrogen atoms were located by difference methods but in the final refinement cycles these were allowed to ride on the parent atom, with Uiso(H) = 1.2Ueq(N) or 1.5Ueq(O)]. Other H atoms were included at calculated positions [C—H (aromatic) = 0.95 Å or C—H (methyl) = 0.98 Å] and allowed to ride, with Uiso(H) = 1.2 or 1.5Ueq(C), respectively. Although not of great importance in this achiral molecule, the Flack parameter (Flack, 1983) was determined as 0.03 (13) for 1569 Friedel pairs. The TwinRotMat check [PLATON (Spek, 2009)] indicated no applicable twin law.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within ORTEP-3 for Windows (Farrugia, 2012); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular conformation and atom-numbering scheme for the cation and anion in the title salt, with the inter-species hydrogen bond shown as a dashed line. Non-H atoms are shown with 40% probability displacement ellipsoids.
[Figure 2] Fig. 2. The two-dimensional structure in the unit cell viewed down the polymer layer, showing hydrogen-bonding associations as dashed lines. Non-associative H-atoms are omitted.
4-Methoxyanilinium 2-carboxy-4,5-dichlorobenzoate top
Crystal data top
C7H10NO+·C8H3Cl2O4−Dx = 1.511 Mg m−3
Mr = 358.16Melting point: 473 K
Orthorhombic, C2221Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c 2Cell parameters from 2436 reflections
a = 7.5319 (8) Åθ = 3.7–28.1°
b = 12.9302 (14) ŵ = 0.44 mm−1
c = 32.3268 (18) ÅT = 200 K
V = 3148.3 (5) Å3Plate, colourless
Z = 80.35 × 0.30 × 0.15 mm
F(000) = 1472
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer		2730 independent reflections
Radiation source: Enhance (Mo) X-ray source2620 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 16.077 pixels mm-1θmax = 25.0°, θmin = 3.1°
ω scansh = −8→8
Absorption correction: multi-scan
(CrysAlis PRO, Agilent, 2012)		k = −15→16
Tmin = 0.759, Tmax = 0.980l = −38→38
6518 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0003P)2 + 10.2538P]
where P = (Fo2 + 2Fc2)/3
S = 1.42(Δ/σ)max = 0.001
2730 reflectionsΔρmax = 0.32 e Å−3
208 parametersΔρmin = −0.33 e Å−3
0 restraintsAbsolute structure: Flack (1983), 1569 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (13)
Crystal data top
C7H10NO+·C8H3Cl2O4−V = 3148.3 (5) Å3
Mr = 358.16Z = 8
Orthorhombic, C2221Mo Kα radiation
a = 7.5319 (8) ŵ = 0.44 mm−1
b = 12.9302 (14) ÅT = 200 K
c = 32.3268 (18) Å0.35 × 0.30 × 0.15 mm
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer		2730 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO, Agilent, 2012)		2620 reflections with I > 2σ(I)
Tmin = 0.759, Tmax = 0.980Rint = 0.036
6518 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0003P)2 + 10.2538P]
where P = (Fo2 + 2Fc2)/3
S = 1.42Δρmax = 0.32 e Å−3
2730 reflectionsΔρmin = −0.33 e Å−3
208 parametersAbsolute structure: Flack (1983), 1569 Friedel pairs
0 restraintsAbsolute structure parameter: 0.03 (13)
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
xyzUiso*/Ueq
Cl41.0614 (2)0.04524 (14)0.69649 (4)0.0504 (5)
Cl50.6536 (2)0.09989 (13)0.70946 (4)0.0482 (5)
O110.5402 (5)0.1011 (3)0.53015 (10)0.0269 (11)
O120.5633 (4)0.2669 (2)0.54919 (9)0.0213 (10)
O210.9047 (5)0.1895 (3)0.51574 (10)0.0281 (11)
O221.1354 (5)0.0921 (3)0.53458 (11)0.0380 (12)
C10.7212 (6)0.1407 (3)0.58796 (14)0.0170 (14)
C20.9001 (5)0.1197 (3)0.58236 (14)0.0147 (12)
C31.0023 (7)0.0889 (4)0.61632 (14)0.0240 (16)
C40.9274 (7)0.0827 (4)0.65531 (15)0.0270 (17)
C50.7505 (8)0.1047 (4)0.66078 (13)0.0263 (16)
C60.6454 (7)0.1346 (4)0.62745 (13)0.0233 (16)
C110.6000 (6)0.1710 (4)0.55224 (14)0.0163 (12)
C210.9909 (6)0.1314 (3)0.54121 (15)0.0200 (16)
O4A1.2905 (6)0.3233 (4)0.67922 (14)0.0607 (19)
N1A0.8469 (5)0.4080 (3)0.54416 (11)0.0233 (11)
C1A0.9599 (6)0.3876 (3)0.58068 (14)0.0203 (14)
C2A1.1396 (7)0.3733 (4)0.57540 (15)0.0270 (17)
C3A1.2440 (8)0.3499 (4)0.60887 (18)0.0350 (17)
C4A1.1695 (8)0.3463 (4)0.64817 (18)0.0333 (19)
C5A0.9921 (8)0.3605 (5)0.65369 (16)0.037 (2)
C6A0.8838 (7)0.3818 (4)0.61917 (15)0.0270 (17)
C41A1.2233 (11)0.3165 (6)0.71999 (19)0.072 (3)
H31.124100.072200.612600.0290*
H60.523600.150700.631400.0280*
H210.966200.206400.491000.0420*
H2A1.191100.379600.548700.0320*
H3A1.366900.336300.605200.0420*
H5A0.941600.356100.680600.0450*
H6A0.759700.392000.622500.0330*
H11A0.803500.465200.544700.0280*
H12A0.894100.400300.519800.0280*
H13A0.754600.355800.549900.0280*
H41A1.320100.299600.739100.1080*
H42A1.132500.262300.721300.1080*
H43A1.170600.382900.727900.1080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl40.0580 (10)0.0630 (11)0.0301 (7)0.0060 (9)−0.0209 (7)0.0088 (7)
Cl50.0724 (11)0.0539 (10)0.0182 (6)0.0038 (9)0.0077 (7)0.0036 (7)
O110.031 (2)0.0218 (18)0.0280 (17)−0.0087 (16)−0.0101 (16)0.0035 (16)
O120.0197 (18)0.0207 (18)0.0236 (16)0.0035 (15)−0.0036 (15)0.0038 (14)
O210.027 (2)0.036 (2)0.0213 (17)0.0074 (17)0.0072 (15)0.0107 (15)
O220.030 (2)0.044 (2)0.040 (2)0.017 (2)0.0067 (18)0.0123 (19)
C10.026 (3)0.005 (2)0.020 (2)−0.0021 (19)−0.003 (2)0.0001 (19)
C20.010 (2)0.006 (2)0.028 (2)0.0044 (18)0.0030 (19)0.0034 (18)
C30.028 (3)0.014 (2)0.030 (3)−0.006 (2)−0.008 (2)0.001 (2)
C40.038 (3)0.014 (3)0.029 (3)0.006 (2)−0.016 (3)0.003 (2)
C50.041 (3)0.022 (3)0.016 (2)0.000 (3)−0.002 (2)0.002 (2)
C60.024 (3)0.022 (3)0.024 (2)0.000 (2)−0.001 (2)0.000 (2)
C110.007 (2)0.019 (2)0.023 (2)−0.0040 (19)0.0051 (18)0.005 (2)
C210.016 (3)0.011 (2)0.033 (3)−0.003 (2)0.002 (2)0.006 (2)
O4A0.061 (3)0.075 (4)0.046 (3)0.013 (3)−0.024 (2)0.010 (2)
N1A0.027 (2)0.020 (2)0.0228 (19)−0.0015 (19)0.0007 (18)0.0026 (18)
C1A0.028 (3)0.007 (2)0.026 (2)−0.006 (2)−0.003 (2)−0.001 (2)
C2A0.022 (3)0.026 (3)0.033 (3)−0.001 (2)0.003 (2)0.002 (2)
C3A0.030 (3)0.027 (3)0.048 (3)−0.001 (3)−0.004 (3)0.000 (3)
C4A0.039 (4)0.019 (3)0.042 (3)−0.003 (3)−0.018 (3)0.004 (2)
C5A0.054 (4)0.038 (4)0.020 (3)−0.004 (3)0.002 (2)0.002 (2)
C6A0.033 (3)0.016 (3)0.032 (3)0.003 (2)0.004 (2)−0.002 (2)
C41A0.108 (7)0.065 (5)0.043 (4)−0.007 (5)−0.030 (4)0.016 (4)
Geometric parameters (Å, º) top
Cl4—C41.739 (5)C3—C41.383 (7)
Cl5—C51.736 (5)C4—C51.374 (8)
O11—C111.237 (6)C5—C61.392 (7)
O12—C111.274 (6)C3—H30.9500
O21—C211.290 (6)C6—H60.9500
O22—C211.220 (6)C1A—C6A1.372 (7)
O21—H210.9500C1A—C2A1.377 (7)
O4A—C41A1.415 (8)C2A—C3A1.371 (8)
O4A—C4A1.388 (7)C3A—C4A1.390 (8)
N1A—C1A1.479 (6)C4A—C5A1.361 (9)
N1A—H13A0.9900C5A—C6A1.409 (7)
N1A—H11A0.8100C2A—H2A0.9500
N1A—H12A0.8700C3A—H3A0.9500
C1—C111.523 (6)C5A—H5A0.9500
C1—C61.401 (6)C6A—H6A0.9500
C1—C21.386 (6)C41A—H41A0.9800
C2—C31.399 (6)C41A—H42A0.9800
C2—C211.503 (6)C41A—H43A0.9800
C21—O21—H21115.00C2—C3—H3120.00
C4A—O4A—C41A116.9 (5)C4—C3—H3120.00
H11A—N1A—H12A107.00C1—C6—H6120.00
C1A—N1A—H13A98.00C5—C6—H6120.00
H12A—N1A—H13A112.00C2A—C1A—C6A121.1 (4)
H11A—N1A—H13A110.00N1A—C1A—C6A119.6 (4)
C1A—N1A—H12A118.00N1A—C1A—C2A119.4 (4)
C1A—N1A—H11A112.00C1A—C2A—C3A119.7 (5)
C2—C1—C11122.3 (4)C2A—C3A—C4A119.8 (5)
C6—C1—C11117.5 (4)O4A—C4A—C3A113.8 (5)
C2—C1—C6120.3 (4)O4A—C4A—C5A125.4 (5)
C1—C2—C21122.5 (4)C3A—C4A—C5A120.8 (5)
C1—C2—C3119.2 (4)C4A—C5A—C6A119.4 (5)
C3—C2—C21118.2 (4)C1A—C6A—C5A119.1 (5)
C2—C3—C4120.5 (5)C1A—C2A—H2A120.00
C3—C4—C5120.1 (5)C3A—C2A—H2A120.00
Cl4—C4—C3118.5 (4)C2A—C3A—H3A120.00
Cl4—C4—C5121.5 (4)C4A—C3A—H3A120.00
Cl5—C5—C6118.2 (4)C4A—C5A—H5A120.00
C4—C5—C6120.6 (4)C6A—C5A—H5A120.00
Cl5—C5—C4121.1 (4)C1A—C6A—H6A120.00
C1—C6—C5119.3 (5)C5A—C6A—H6A120.00
O11—C11—O12126.0 (4)O4A—C41A—H41A110.00
O11—C11—C1117.9 (4)O4A—C41A—H42A110.00
O12—C11—C1116.0 (4)O4A—C41A—H43A109.00
O21—C21—O22125.4 (5)H41A—C41A—H42A109.00
O21—C21—C2113.2 (4)H41A—C41A—H43A109.00
O22—C21—C2121.3 (4)H42A—C41A—H43A109.00
C41A—O4A—C4A—C5A−1.5 (9)C2—C3—C4—Cl4−179.4 (4)
C41A—O4A—C4A—C3A−178.9 (5)C2—C3—C4—C51.4 (8)
C6—C1—C2—C21−176.1 (4)Cl4—C4—C5—C6180.0 (4)
C6—C1—C2—C32.2 (6)C3—C4—C5—Cl5−178.8 (4)
C2—C1—C6—C5−1.6 (7)Cl4—C4—C5—Cl52.0 (7)
C11—C1—C6—C5178.4 (4)C3—C4—C5—C6−0.8 (8)
C2—C1—C11—O1181.2 (6)C4—C5—C6—C10.9 (8)
C2—C1—C11—O12−101.9 (5)Cl5—C5—C6—C1179.0 (4)
C6—C1—C11—O11−98.9 (5)N1A—C1A—C2A—C3A−177.2 (4)
C11—C1—C2—C3−177.8 (4)C6A—C1A—C2A—C3A1.9 (7)
C11—C1—C2—C213.8 (6)N1A—C1A—C6A—C5A178.9 (5)
C6—C1—C11—O1278.0 (5)C2A—C1A—C6A—C5A−0.2 (7)
C1—C2—C21—O2119.1 (6)C1A—C2A—C3A—C4A−3.5 (8)
C1—C2—C21—O22−163.9 (4)C2A—C3A—C4A—O4A−179.1 (5)
C21—C2—C3—C4176.3 (4)C2A—C3A—C4A—C5A3.4 (8)
C3—C2—C21—O2217.8 (6)O4A—C4A—C5A—C6A−178.9 (5)
C3—C2—C21—O21−159.3 (4)C3A—C4A—C5A—C6A−1.7 (9)
C1—C2—C3—C4−2.1 (7)C4A—C5A—C6A—C1A0.1 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H11A···O11i0.812.552.926 (5)110
N1A—H11A···O22ii0.812.102.881 (5)163
N1A—H12A···O11iii0.871.952.811 (5)168
N1A—H13A···O120.991.842.814 (5)167
O21—H21···O12iii0.951.532.480 (4)179
C3A—H3A···O12iv0.952.503.265 (7)137
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x−1/2, y+1/2, z; (iii) x+1/2, −y+1/2, −z+1; (iv) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H11A···O22i0.812.102.881 (5)163
N1A—H12A···O11ii0.871.952.811 (5)168
N1A—H13A···O120.991.842.814 (5)167
O21—H21···O12ii0.951.532.480 (4)179
C3A—H3A···O12iii0.952.503.265 (7)137
Symmetry codes: (i) x−1/2, y+1/2, z; (ii) x+1/2, −y+1/2, −z+1; (iii) x+1, y, z.
 

Acknowledgements

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

References

First citationAgilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.  Google Scholar
 First citationAltomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350.  CrossRef Web of Science IUCr Journals Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationMattes, R. & Dorau, A. (1986). Z. Naturforsch. Chem. Sci. 41, 808–814.  Google Scholar
 First citationOdabaşoğlu, M. & Büyükgüngör, O. (2007). Acta Cryst. E63, o4374–o4375.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSmith, G., Wermuth, U. D. & White, J. M. (2009). Acta Cryst. E65, o2111.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSmith, G. & Wermuth, U. D. (2012). Acta Cryst. E68, o1928.  CSD CrossRef IUCr Journals Google Scholar
 First citationSmith, G., Wermuth, U. D. & White, J. M. (2008a). Acta Cryst. C64, o180–o183.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationSmith, G., Wermuth, U. D. & White, J. M. (2008b). Acta Cryst. C64, o532–o536.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 10| October 2013| Page o1546
doi:10.1107/S1600536813025014
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS