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 67| Part 12| December 2011| Page o3317
https://doi.org/10.1107/S1600536811047817

N-(4-Chloro-2-methyl­phen­yl)maleamic acid

K. Shakuntala,a Viktor Vrábel,b B. Thimme Gowdaa* and Jozef Kožíšekb

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
*Correspondence e-mail: gowdabt@yahoo.com

(Received 8 November 2011; accepted 10 November 2011; online 16 November 2011)

In the mol­ecular structure of the title compound, C11H10ClNO3, the conformation of the N—H bond in the amide segment is syn to the ortho-methyl group in the phenyl ring. The C=O and O—H bonds of the acid group are in the relatively rare anti position with respect to each other. This is an obvious consequence of the hydrogen bond donated to the amide carbonyl group. The central oxobutenoic acid core C(=O)—C=C—C—OH is twisted by 31.65 (6)° out of the plane of the 4-chloro-2-methyl­phenyl ring. An intra­molecular O—H⋯O hydrogen bond occurs. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into infinite chains running along the a axis.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2000[Gowda, B. T., Paulus, H. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 791-800.], 2010[Gowda, B. T., Tokarčík, M., Shakuntala, K., Kožíšek, J. & Fuess, H. (2010). Acta Cryst. E66, o1554.]); Prasad et al. (2002[Prasad, S. M., Sinha, R. B. P., Mandal, D. K. & Rani, A. (2002). Acta Cryst. E58, o1296-o1297.]), on N-(ar­yl)-methane­sulfonamides, see: Jayalakshmi & Gowda (2004[Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.]), on N-(ar­yl)-aryl­sulfonamides, see: Shetty & Gowda (2005[Shetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113-120.]) and on N-chloro­aryl­sulfonamides, see: Gowda & Kumar (2003[Gowda, B. T. & Kumar, B. H. A. (2003). Oxid. Commun. A, 26, 403-425.]). For modes of inter­linking carb­oxy­lic acids by hydrogen bonds, see: Leiserowitz (1976[Leiserowitz, L. (1976). Acta Cryst. B32, 775-802.])

[Scheme 1]

Experimental

Crystal data

  • C11H10ClNO3

  • Mr = 239.65

  • Orthorhombic, P b c a

  • a = 12.1310 (11) Å

  • b = 7.3990 (7) Å

  • c = 25.466 (2) Å

  • V = 2285.7 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.33 mm−1

  • T = 295 K

  • 0.45 × 0.35 × 0.25 mm
Data collection

  • Oxford Diffraction Xcalibur diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.865, Tmax = 0.918

  • 17740 measured reflections

  • 1819 independent reflections

  • 1642 reflections with I > 2σ(I)

  • Rint = 0.025
Refinement

  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.089

  • S = 1.02

  • 1819 reflections

  • 154 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O3i 0.86 (1) 2.10 (1) 2.9556 (19) 174 (2)
O2—H2A⋯O1 0.92 (1) 1.57 (1) 2.4797 (17) 171 (3)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2002[Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811047817/bq2317sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047817/bq2317Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811047817/bq2317Isup3.cml

checkCIF report


Comment top

The amide moiety is the constituent of many biologically significant compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2000, 2010), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloroarylsulfoamides (Gowda & Kumar, 2003), in the present work, the crystal structure of N-(4-chloro-2-methylphenyl)-maleamic acid (I) has been determined (Fig.1).

The conformations of the N—H and the C=O bonds in the amide segment are anti to each other. But the conformation of the N—H bond is syn to the ortho-methyl group in the phenyl ring. In the maleamic acid moiety, the amide C=O bond is anti to the adjacent C—H bond, while the carboxyl C=O bond is syn to the adjacent C—H bond. The observed rare anti conformation of the C=O and O—H bonds of the acid group is similar to that observed in N-(2-methylphenyl)-maleamic acid (Gowda et al., 2010). This is an obvious consequence of the hydrogen bond donated to the amide carbonyl group. The central oxobutenoic acid core C(=O)—C=C—C—OH is twisted by 31.65 (6)° out of the plane of the 4-chloro-2-methylphenyl ring. The C2–C3 bond length of 1.333 (2)Å clearly indicates the double bond character.

The various modes of interlinking carboxylic acids by hydrogen bonds is described elsewhere (Leiserowitz, 1976).

In (I), both the intramolecular O–H···O and intermolecular N–H···O hydrogen bonds have been observed. The packing of molecules linked by N—H···O hydrogen bonds into infinite chains running along the a-axis is shown in Fig. 2.

Related literature top

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2000, 2010); Prasad et al. (2002), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004), onN-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005) and on N-chloroarylsulfonamides, see: Gowda & Kumar (2003). For modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976)

Experimental top

The solution of maleic anhydride (0.025 mol) in toluene (25 ml) was treated dropwise with the solution of 4-chloro-2-methylaniline (0.025 mol) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for about 30 min. and set aside for an additional 30 min. at room temperature for the completion of reaction. The mixture was then treated with dilute hydrochloric acid to remove the unreacted 4-chloro-2-methylaniline. The resultant solid N-(4-chloro-2-methylphenyl)-maleamic acid was filtered under suction and washed thoroughly with water to remove the unreacted maleic anhydride and maleic acid. It was recrystallized to constant melting point from ethanol. The purity of the compound was checked by elemental analysis and characterized by its infrared spectra.

The plate like colorless single crystals of the title compound used in X-ray diffraction studies were grown in an ethanol solution by slow evaporation (0.5 g in about 30 ml of ethanol) at room temperature.

Refinement top

All hydrogen atoms were placed in calculated positions with C–H distances of 0.93Å (C-aromatic) and 0.96Å (C-methyl), and constrained to ride on their parent atoms. Amide and O—H atoms were seen in difference map and were refined with the N—H and O—H distances restrained to 0.86 (1)Å and 0.92 (1) Å, respectively. The Uiso(H) values were set at 1.2 Ueq (C-aromatic, N) or 1.5Ueq (C-methyl).

Structure description top

The amide moiety is the constituent of many biologically significant compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2000, 2010), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloroarylsulfoamides (Gowda & Kumar, 2003), in the present work, the crystal structure of N-(4-chloro-2-methylphenyl)-maleamic acid (I) has been determined (Fig.1).

The conformations of the N—H and the C=O bonds in the amide segment are anti to each other. But the conformation of the N—H bond is syn to the ortho-methyl group in the phenyl ring. In the maleamic acid moiety, the amide C=O bond is anti to the adjacent C—H bond, while the carboxyl C=O bond is syn to the adjacent C—H bond. The observed rare anti conformation of the C=O and O—H bonds of the acid group is similar to that observed in N-(2-methylphenyl)-maleamic acid (Gowda et al., 2010). This is an obvious consequence of the hydrogen bond donated to the amide carbonyl group. The central oxobutenoic acid core C(=O)—C=C—C—OH is twisted by 31.65 (6)° out of the plane of the 4-chloro-2-methylphenyl ring. The C2–C3 bond length of 1.333 (2)Å clearly indicates the double bond character.

The various modes of interlinking carboxylic acids by hydrogen bonds is described elsewhere (Leiserowitz, 1976).

In (I), both the intramolecular O–H···O and intermolecular N–H···O hydrogen bonds have been observed. The packing of molecules linked by N—H···O hydrogen bonds into infinite chains running along the a-axis is shown in Fig. 2.

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2000, 2010); Prasad et al. (2002), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004), onN-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005) and on N-chloroarylsulfonamides, see: Gowda & Kumar (2003). For modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976)

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing the atom labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing view of the title compound. Molecular chains along a-axis are generated by N–H···O hydrogen bonds which are shown as dashed lines. H atoms not involved in H-bonding have been omitted.
N-(4-Chloro-2-methylphenyl)maleamic acid top
Crystal data top
C11H10ClNO3Dx = 1.393 Mg m−3
Mr = 239.65Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 1819 reflections
a = 12.1310 (11) Åθ = 3.6–24.4°
b = 7.3990 (7) ŵ = 0.33 mm−1
c = 25.466 (2) ÅT = 295 K
V = 2285.7 (3) Å3Plate, colourless
Z = 80.45 × 0.35 × 0.25 mm
F(000) = 992
Data collection top
Oxford Diffraction Xcalibur
diffractometer		1819 independent reflections
Radiation source: fine-focus sealed tube1642 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 0 pixels mm-1θmax = 24.4°, θmin = 3.6°
ω scans with κ offsetsh = −14→13
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		k = −8→8
Tmin = 0.865, Tmax = 0.918l = −29→28
17740 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0445P)2 + 0.9459P]
where P = (Fo2 + 2Fc2)/3
1819 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.19 e Å−3
2 restraintsΔρmin = −0.27 e Å−3
Crystal data top
C11H10ClNO3V = 2285.7 (3) Å3
Mr = 239.65Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 12.1310 (11) ŵ = 0.33 mm−1
b = 7.3990 (7) ÅT = 295 K
c = 25.466 (2) Å0.45 × 0.35 × 0.25 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer		1819 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		1642 reflections with I > 2σ(I)
Tmin = 0.865, Tmax = 0.918Rint = 0.025
17740 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0332 restraints
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.19 e Å−3
1819 reflectionsΔρmin = −0.27 e Å−3
154 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
xyzUiso*/Ueq
C10.29051 (13)0.3610 (2)0.08033 (7)0.0428 (4)
C20.31769 (14)0.3019 (3)0.02624 (7)0.0485 (5)
H20.39250.29170.01880.058*
C30.25011 (15)0.2612 (3)−0.01329 (6)0.0505 (5)
H30.28600.2317−0.04440.061*
C40.12845 (15)0.2543 (3)−0.01670 (7)0.0496 (5)
C50.37645 (12)0.4444 (2)0.16488 (6)0.0368 (4)
C60.46315 (13)0.5525 (2)0.18298 (6)0.0383 (4)
C70.46319 (14)0.6020 (2)0.23578 (6)0.0431 (4)
H70.52050.67230.24890.052*
C80.37918 (14)0.5481 (2)0.26889 (6)0.0410 (4)
C90.29334 (14)0.4439 (2)0.25077 (7)0.0449 (4)
H90.23660.40970.27320.054*
C100.29265 (14)0.3907 (2)0.19860 (7)0.0429 (4)
H100.23570.31850.18610.051*
C110.55428 (15)0.6166 (3)0.14712 (7)0.0517 (5)
H11A0.59370.51410.13360.078*
H11B0.60390.69270.16640.078*
H11C0.52310.68370.11850.078*
N10.37789 (11)0.38698 (19)0.11129 (5)0.0406 (4)
H10.4407 (8)0.369 (2)0.0965 (6)0.046 (5)*
O10.19506 (10)0.3884 (2)0.09562 (5)0.0656 (4)
O20.06813 (10)0.2998 (3)0.02376 (5)0.0746 (5)
H2A0.1092 (19)0.340 (3)0.0519 (7)0.098 (8)*
O30.08638 (11)0.2036 (2)−0.05732 (5)0.0700 (4)
Cl10.38181 (4)0.61481 (7)0.334722 (17)0.0585 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0340 (9)0.0542 (10)0.0401 (9)−0.0017 (8)−0.0029 (7)−0.0048 (8)
C20.0339 (9)0.0681 (12)0.0436 (10)−0.0021 (8)0.0016 (7)−0.0083 (9)
C30.0436 (9)0.0720 (12)0.0359 (9)−0.0057 (9)0.0018 (8)−0.0065 (9)
C40.0438 (10)0.0691 (12)0.0358 (10)−0.0091 (9)−0.0067 (8)0.0037 (9)
C50.0355 (8)0.0380 (8)0.0370 (9)0.0011 (7)−0.0049 (7)−0.0031 (7)
C60.0355 (8)0.0360 (8)0.0434 (9)−0.0009 (7)−0.0029 (7)−0.0012 (7)
C70.0441 (10)0.0389 (9)0.0463 (10)−0.0041 (8)−0.0090 (8)−0.0061 (7)
C80.0509 (10)0.0366 (8)0.0356 (9)0.0025 (8)−0.0047 (7)−0.0026 (7)
C90.0473 (10)0.0460 (9)0.0415 (9)−0.0040 (8)0.0030 (7)0.0015 (8)
C100.0410 (9)0.0452 (9)0.0425 (9)−0.0094 (8)−0.0028 (7)−0.0027 (7)
C110.0440 (10)0.0592 (11)0.0519 (11)−0.0133 (9)0.0002 (8)−0.0048 (9)
N10.0321 (8)0.0517 (9)0.0380 (8)−0.0033 (6)−0.0008 (6)−0.0070 (6)
O10.0350 (7)0.1178 (13)0.0441 (7)0.0058 (7)−0.0029 (5)−0.0196 (7)
O20.0374 (7)0.1425 (15)0.0439 (8)−0.0093 (8)−0.0041 (6)−0.0140 (9)
O30.0527 (8)0.1129 (12)0.0444 (7)−0.0126 (8)−0.0140 (6)−0.0092 (8)
Cl10.0767 (4)0.0599 (3)0.0388 (3)−0.0056 (2)−0.0028 (2)−0.00955 (19)
Geometric parameters (Å, º) top
C1—O11.238 (2)C6—C111.510 (2)
C1—O11.238 (2)C7—C81.382 (2)
C1—N11.335 (2)C7—H70.9300
C1—C21.482 (2)C8—C91.375 (2)
C2—C31.333 (2)C8—Cl11.7478 (16)
C2—H20.9300C9—C101.386 (2)
C3—C41.479 (3)C9—H90.9300
C3—H30.9300C10—H100.9300
C4—O31.213 (2)C11—H11A0.9600
C4—O21.308 (2)C11—H11B0.9600
C5—C101.389 (2)C11—H11C0.9600
C5—C61.400 (2)N1—H10.861 (5)
C5—N11.429 (2)O1—O10.000 (5)
C6—C71.394 (2)O2—H2A0.920 (5)
O1—C1—O10.00 (12)C8—C7—H7119.6
O1—C1—N1122.22 (16)C6—C7—H7119.6
O1—C1—N1122.22 (16)C9—C8—C7121.03 (15)
O1—C1—C2123.26 (15)C9—C8—Cl1119.60 (13)
O1—C1—C2123.26 (15)C7—C8—Cl1119.37 (13)
N1—C1—C2114.50 (14)C8—C9—C10119.05 (16)
C3—C2—C1129.17 (16)C8—C9—H9120.5
C3—C2—H2115.4C10—C9—H9120.5
C1—C2—H2115.4C9—C10—C5120.47 (15)
C2—C3—C4131.75 (17)C9—C10—H10119.8
C2—C3—H3114.1C5—C10—H10119.8
C4—C3—H3114.1C6—C11—H11A109.5
O3—C4—O2121.08 (16)C6—C11—H11B109.5
O3—C4—C3118.71 (17)H11A—C11—H11B109.5
O2—C4—C3120.21 (15)C6—C11—H11C109.5
C10—C5—C6120.67 (15)H11A—C11—H11C109.5
C10—C5—N1120.95 (14)H11B—C11—H11C109.5
C6—C5—N1118.36 (14)C1—N1—C5126.65 (14)
C7—C6—C5117.92 (15)C1—N1—H1114.9 (12)
C7—C6—C11120.05 (15)C5—N1—H1118.4 (12)
C5—C6—C11122.03 (15)O1—O1—C10 (10)
C8—C7—C6120.85 (15)C4—O2—H2A113.1 (17)
O1—C1—C2—C3−3.2 (3)C6—C7—C8—Cl1−179.45 (13)
O1—C1—C2—C3−3.2 (3)C7—C8—C9—C100.9 (3)
N1—C1—C2—C3178.4 (2)Cl1—C8—C9—C10−179.48 (13)
C1—C2—C3—C4−2.4 (4)C8—C9—C10—C5−1.1 (3)
C2—C3—C4—O3−176.3 (2)C6—C5—C10—C90.2 (3)
C2—C3—C4—O22.7 (4)N1—C5—C10—C9178.60 (15)
C10—C5—C6—C70.8 (2)O1—C1—N1—C51.3 (3)
N1—C5—C6—C7−177.59 (14)O1—C1—N1—C51.3 (3)
C10—C5—C6—C11−178.68 (16)C2—C1—N1—C5179.73 (16)
N1—C5—C6—C112.9 (2)C10—C5—N1—C134.9 (3)
C5—C6—C7—C8−1.0 (2)C6—C5—N1—C1−146.67 (17)
C11—C6—C7—C8178.52 (16)N1—C1—O1—O10.00 (10)
C6—C7—C8—C90.1 (3)C2—C1—O1—O10.00 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.86 (1)2.10 (1)2.9556 (19)174 (2)
O2—H2A···O10.92 (1)1.57 (1)2.4797 (17)171 (3)
Symmetry code: (i) x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formulaC11H10ClNO3
Mr239.65
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)295
a, b, c (Å)12.1310 (11), 7.3990 (7), 25.466 (2)
V (Å3)2285.7 (3)
Z8
Radiation typeMo Kα
µ (mm−1)0.33
Crystal size (mm)0.45 × 0.35 × 0.25
Data collection
DiffractometerOxford Diffraction Xcalibur
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.865, 0.918
No. of measured, independent and
observed [I > 2σ(I)] reflections		17740, 1819, 1642
Rint0.025
(sin θ/λ)max (Å−1)0.581
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.089, 1.02
No. of reflections1819
No. of parameters154
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.19, −0.27

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.861 (5)2.099 (6)2.9556 (19)173.6 (17)
O2—H2A···O10.920 (5)1.568 (7)2.4797 (17)171 (3)
Symmetry code: (i) x+1/2, −y+1/2, −z.
 

Acknowledgements

VV and JK thank the VEGA Grant Agency of the Slovak Ministry of Education (1/0679/11) and the Research and Development Agency of Slovakia (APVV-0202–10) for support and the Structural Funds, Inter­reg IIIA, for financial support in purchasing the diffractometer. VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS research fellowship.

References

First citationBrandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationGowda, B. T. & Kumar, B. H. A. (2003). Oxid. Commun. A, 26, 403–425.  CAS Google Scholar
 First citationGowda, B. T., Paulus, H. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 791–800.  CAS Google Scholar
 First citationGowda, B. T., Tokarčík, M., Shakuntala, K., Kožíšek, J. & Fuess, H. (2010). Acta Cryst. E66, o1554.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationJayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491–500.  CAS Google Scholar
 First citationLeiserowitz, L. (1976). Acta Cryst. B32, 775–802.  CrossRef CAS IUCr Journals Web of Science Google Scholar
 First citationOxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationPrasad, S. M., Sinha, R. B. P., Mandal, D. K. & Rani, A. (2002). Acta Cryst. E58, o1296–o1297.  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 citationShetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113–120.  CAS 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 67| Part 12| December 2011| Page o3317
https://doi.org/10.1107/S1600536811047817
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