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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3349
https://doi.org/10.1107/S1600536810048786

N-(2,3-Di­methyl­phen­yl)-4-methyl­benzene­sulfonamide

P. G. Nirmala,a Sabine Foro,b B. Thimme Gowdaa* and Hartmut Fuessc

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287, Darmstadt, Germany, and cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 19 November 2010; accepted 22 November 2010; online 27 November 2010)

In the title compound, C15H17NO2S, the dihedral angle between the aromatic rings is 38.3 (1)°. The conformation of the N—H bond is anti to the methyl groups in the adjacent aromatic ring. In the crystal, N—H⋯O hydrogen bonds link the molecules into infinite chains.

Related literature

For the preparation of the title compound, see: Shetty & Gowda (2005[Shetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113-120.]). For our study of the effects of substituents on the structures of N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2009a[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2009a). Acta Cryst. E65, o366.],b[Gowda, B. T., Foro, S., Nirmala, P. G., Terao, H. & Fuess, H. (2009b). Acta Cryst. E65, o1219.]; 2010[Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o15.]); For related structures, see: Gelbrich et al. (2007[Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621-632.]); Perlovich et al. (2006[Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780-o782.])

[Scheme 1]

Experimental

Crystal data

  • C15H17NO2S

  • Mr = 275.36

  • Monoclinic, P 21 /c

  • a = 10.771 (1) Å

  • b = 13.357 (1) Å

  • c = 9.9667 (9) Å

  • β = 93.256 (8)°

  • V = 1431.6 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 299 K

  • 0.40 × 0.28 × 0.24 mm
Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.916, Tmax = 0.948

  • 5990 measured reflections

  • 2924 independent reflections

  • 2283 reflections with I > 2σ(I)

  • Rint = 0.016
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.118

  • S = 1.05

  • 2924 reflections

  • 178 parameters

  • 1 restraint

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

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O1i 0.85 (1) 2.08 (1) 2.8999 (19) 165 (2)
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810048786/bq2256sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048786/bq2256Isup2.hkl

checkCIF report


Comment top

As part of a study of the substituent effects on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2009a, b; 2010), the structure of 4-methyl-N-(2,3-dimethylphenyl)-benzenesulfonamide (I) has been determined (Fig. 1). The conformation of the N—H bond in (I) is anti to the ortho- and meta-methyl groups. The molecule is bent at the S atom with the C—SO2—NH—C torsion angle of 80.2 (2)°, compared to the values of -61.0 (2)° in 4-methyl-N-(2,5-dimethylphenyl)-benzenesulfonamide (II) (Gowda et al., 2010), -51.6 (3)° in 4-Methyl-N-(phenyl)- benzenesulfonamide (III) (Gowda et al., 2009b) and 71.0 (2)° in N-(2,3-dimethylphenyl)benzenesulfonamide (IV) (Gowda et al., 2009a). The two benzene rings in (I) are tilted relative to each other by 38.3 (1)°, compared to the values of 49.4 (1)° in (II), 68.4 (1)° in (III) and 64.8 (1)° in (IV). The other bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The packing of molecules via N—H···O hydrogen bonds (Table 1) into infinite chains is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Shetty & Gowda (2005). For our study of the effects of substituents on the structures of N-(aryl)-arylsulfonamides, see: Gowda et al. (2009a,b; 2010); For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006)

Experimental top

The solution of toluene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0 ° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 4-methylbenzenesulfonylchloride was treated with 2,3-dimethylaniline in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant 4-methyl-N-(2,3-dimethylphenyl)benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra (Shetty & Gowda, 2005).

Rod like colourless single crystals used in X-ray diffraction studies were grown in ethanolic solution by a slow evaporation at room temperature.

Refinement top

The H atom of the NH group was located in a difference map and later restrained to the distance N—H = 0.86 (1) Å. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

Structure description top

As part of a study of the substituent effects on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2009a, b; 2010), the structure of 4-methyl-N-(2,3-dimethylphenyl)-benzenesulfonamide (I) has been determined (Fig. 1). The conformation of the N—H bond in (I) is anti to the ortho- and meta-methyl groups. The molecule is bent at the S atom with the C—SO2—NH—C torsion angle of 80.2 (2)°, compared to the values of -61.0 (2)° in 4-methyl-N-(2,5-dimethylphenyl)-benzenesulfonamide (II) (Gowda et al., 2010), -51.6 (3)° in 4-Methyl-N-(phenyl)- benzenesulfonamide (III) (Gowda et al., 2009b) and 71.0 (2)° in N-(2,3-dimethylphenyl)benzenesulfonamide (IV) (Gowda et al., 2009a). The two benzene rings in (I) are tilted relative to each other by 38.3 (1)°, compared to the values of 49.4 (1)° in (II), 68.4 (1)° in (III) and 64.8 (1)° in (IV). The other bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The packing of molecules via N—H···O hydrogen bonds (Table 1) into infinite chains is shown in Fig. 2.

For the preparation of the title compound, see: Shetty & Gowda (2005). For our study of the effects of substituents on the structures of N-(aryl)-arylsulfonamides, see: Gowda et al. (2009a,b; 2010); For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006)

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom labeling scheme and displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.
N-(2,3-Dimethylphenyl)-4-methylbenzenesulfonamide top
Crystal data top
C15H17NO2SF(000) = 584
Mr = 275.36Dx = 1.278 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2134 reflections
a = 10.771 (1) Åθ = 2.7–27.8°
b = 13.357 (1) ŵ = 0.22 mm−1
c = 9.9667 (9) ÅT = 299 K
β = 93.256 (8)°Rod, colourless
V = 1431.6 (2) Å30.40 × 0.28 × 0.24 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2924 independent reflections
Radiation source: fine-focus sealed tube2283 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Rotation method data acquisition using ω and phi scans.θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −13→13
Tmin = 0.916, Tmax = 0.948k = −16→16
5990 measured reflectionsl = −12→12
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0541P)2 + 0.5306P]
where P = (Fo2 + 2Fc2)/3
2924 reflections(Δ/σ)max = 0.003
178 parametersΔρmax = 0.21 e Å−3
1 restraintΔρmin = −0.33 e Å−3
Crystal data top
C15H17NO2SV = 1431.6 (2) Å3
Mr = 275.36Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.771 (1) ŵ = 0.22 mm−1
b = 13.357 (1) ÅT = 299 K
c = 9.9667 (9) Å0.40 × 0.28 × 0.24 mm
β = 93.256 (8)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2924 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		2283 reflections with I > 2σ(I)
Tmin = 0.916, Tmax = 0.948Rint = 0.016
5990 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0451 restraint
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.21 e Å−3
2924 reflectionsΔρmin = −0.33 e Å−3
178 parameters
Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C10.8751 (2)0.83403 (14)0.00059 (18)0.0416 (5)
C20.9745 (2)0.79149 (16)0.0754 (2)0.0541 (6)
H20.96030.75330.15110.065*
C31.0950 (2)0.80616 (18)0.0367 (3)0.0618 (6)
H31.16100.77730.08700.074*
C41.1192 (2)0.86297 (18)−0.0755 (2)0.0597 (6)
C51.0186 (3)0.90574 (18)−0.1467 (2)0.0615 (6)
H51.03300.9452−0.22120.074*
C60.8977 (2)0.89196 (16)−0.1112 (2)0.0532 (5)
H60.83200.9212−0.16160.064*
C70.70153 (17)0.61341 (14)0.01859 (17)0.0370 (4)
C80.62354 (17)0.56874 (15)0.10963 (17)0.0388 (4)
C90.6555 (2)0.47214 (16)0.15710 (19)0.0474 (5)
C100.7613 (2)0.42509 (17)0.1120 (2)0.0566 (6)
H100.78290.36190.14500.068*
C110.8345 (2)0.46986 (18)0.0199 (2)0.0574 (6)
H110.90330.4363−0.01040.069*
C120.80522 (18)0.56454 (16)−0.0271 (2)0.0468 (5)
H120.85430.5955−0.08870.056*
C131.2511 (3)0.8780 (2)−0.1188 (3)0.0863 (9)
H13A1.30530.8298−0.07430.104*
H13B1.27880.9443−0.09510.104*
H13C1.25260.8693−0.21430.104*
C140.50770 (19)0.62004 (18)0.1532 (2)0.0541 (6)
H14A0.49440.68070.10270.065*
H14B0.51740.63560.24730.065*
H14C0.43750.57640.13740.065*
C150.5750 (3)0.4194 (2)0.2541 (2)0.0715 (8)
H15A0.49170.41400.21500.086*
H15B0.57440.45710.33610.086*
H15C0.60770.35370.27280.086*
N10.66972 (16)0.71156 (12)−0.03365 (15)0.0418 (4)
H1N0.674 (2)0.7188 (16)−0.1175 (10)0.050*
O10.72272 (15)0.79141 (12)0.18435 (13)0.0561 (4)
O20.64468 (16)0.89283 (12)−0.01147 (17)0.0629 (4)
S10.71972 (5)0.81273 (4)0.04301 (5)0.04238 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0596 (12)0.0339 (10)0.0315 (9)−0.0002 (9)0.0038 (8)−0.0015 (8)
C20.0682 (15)0.0489 (13)0.0451 (12)0.0008 (11)0.0017 (11)0.0089 (10)
C30.0572 (14)0.0599 (15)0.0678 (16)−0.0013 (12)−0.0016 (12)−0.0013 (12)
C40.0666 (15)0.0534 (14)0.0606 (14)−0.0176 (12)0.0150 (12)−0.0203 (12)
C50.0842 (18)0.0578 (14)0.0438 (12)−0.0181 (13)0.0151 (12)0.0006 (11)
C60.0710 (15)0.0511 (13)0.0377 (11)−0.0025 (11)0.0035 (10)0.0070 (9)
C70.0402 (10)0.0413 (10)0.0295 (9)−0.0032 (8)0.0026 (7)−0.0030 (8)
C80.0385 (10)0.0495 (12)0.0284 (9)−0.0088 (9)0.0018 (7)−0.0042 (8)
C90.0575 (13)0.0475 (12)0.0365 (10)−0.0180 (10)−0.0030 (9)−0.0004 (9)
C100.0684 (15)0.0395 (12)0.0606 (14)−0.0015 (11)−0.0082 (12)0.0003 (10)
C110.0512 (13)0.0514 (13)0.0701 (15)0.0085 (11)0.0066 (11)−0.0062 (11)
C120.0450 (11)0.0494 (12)0.0472 (11)−0.0024 (9)0.0133 (9)−0.0052 (9)
C130.0745 (18)0.086 (2)0.101 (2)−0.0270 (16)0.0265 (16)−0.0226 (17)
C140.0445 (11)0.0740 (16)0.0450 (12)−0.0075 (11)0.0133 (9)−0.0088 (11)
C150.096 (2)0.0647 (16)0.0538 (14)−0.0357 (15)0.0068 (13)0.0085 (12)
N10.0550 (10)0.0458 (9)0.0248 (7)0.0013 (8)0.0052 (7)0.0017 (7)
O10.0795 (11)0.0646 (10)0.0252 (7)−0.0021 (8)0.0122 (7)−0.0056 (6)
O20.0750 (11)0.0496 (9)0.0645 (10)0.0206 (8)0.0076 (8)0.0036 (8)
S10.0589 (3)0.0400 (3)0.0290 (2)0.0067 (2)0.0089 (2)−0.00128 (19)
Geometric parameters (Å, º) top
C1—C61.389 (3)C10—C111.381 (3)
C1—C21.391 (3)C10—H100.9300
C1—S11.773 (2)C11—C121.379 (3)
C2—C31.389 (3)C11—H110.9300
C2—H20.9300C12—H120.9300
C3—C41.388 (3)C13—H13A0.9600
C3—H30.9300C13—H13B0.9600
C4—C51.385 (4)C13—H13C0.9600
C4—C131.522 (3)C14—H14A0.9600
C5—C61.381 (3)C14—H14B0.9600
C5—H50.9300C14—H14C0.9600
C6—H60.9300C15—H15A0.9600
C7—C121.392 (3)C15—H15B0.9600
C7—C81.404 (2)C15—H15C0.9600
C7—N11.445 (2)N1—S11.6288 (17)
C8—C91.410 (3)N1—H1N0.845 (9)
C8—C141.509 (3)O1—S11.4357 (14)
C9—C101.398 (3)O2—S11.4294 (16)
C9—C151.509 (3)
C6—C1—C2119.6 (2)C10—C11—H11120.2
C6—C1—S1119.42 (17)C11—C12—C7119.44 (19)
C2—C1—S1121.00 (15)C11—C12—H12120.3
C3—C2—C1119.8 (2)C7—C12—H12120.3
C3—C2—H2120.1C4—C13—H13A109.5
C1—C2—H2120.1C4—C13—H13B109.5
C4—C3—C2121.5 (2)H13A—C13—H13B109.5
C4—C3—H3119.3C4—C13—H13C109.5
C2—C3—H3119.3H13A—C13—H13C109.5
C5—C4—C3117.5 (2)H13B—C13—H13C109.5
C5—C4—C13121.1 (2)C8—C14—H14A109.5
C3—C4—C13121.4 (3)C8—C14—H14B109.5
C6—C5—C4122.4 (2)H14A—C14—H14B109.5
C6—C5—H5118.8C8—C14—H14C109.5
C4—C5—H5118.8H14A—C14—H14C109.5
C5—C6—C1119.3 (2)H14B—C14—H14C109.5
C5—C6—H6120.3C9—C15—H15A109.5
C1—C6—H6120.3C9—C15—H15B109.5
C12—C7—C8122.17 (19)H15A—C15—H15B109.5
C12—C7—N1119.07 (16)C9—C15—H15C109.5
C8—C7—N1118.70 (17)H15A—C15—H15C109.5
C7—C8—C9117.52 (18)H15B—C15—H15C109.5
C7—C8—C14121.86 (19)C7—N1—S1121.23 (13)
C9—C8—C14120.59 (18)C7—N1—H1N115.7 (15)
C10—C9—C8119.44 (18)S1—N1—H1N109.4 (15)
C10—C9—C15120.3 (2)O2—S1—O1120.12 (9)
C8—C9—C15120.2 (2)O2—S1—N1106.14 (10)
C11—C10—C9121.8 (2)O1—S1—N1106.51 (9)
C11—C10—H10119.1O2—S1—C1108.09 (10)
C9—C10—H10119.1O1—S1—C1107.27 (10)
C12—C11—C10119.6 (2)N1—S1—C1108.23 (9)
C12—C11—H11120.2
C6—C1—C2—C3−0.9 (3)C8—C9—C10—C11−1.3 (3)
S1—C1—C2—C3177.42 (17)C15—C9—C10—C11177.8 (2)
C1—C2—C3—C40.2 (4)C9—C10—C11—C121.7 (4)
C2—C3—C4—C50.8 (3)C10—C11—C12—C7−0.4 (3)
C2—C3—C4—C13−179.3 (2)C8—C7—C12—C11−1.2 (3)
C3—C4—C5—C6−1.2 (3)N1—C7—C12—C11−178.47 (18)
C13—C4—C5—C6178.8 (2)C12—C7—N1—S1−93.10 (19)
C4—C5—C6—C10.6 (3)C8—C7—N1—S189.58 (19)
C2—C1—C6—C50.5 (3)C7—N1—S1—O2−163.99 (14)
S1—C1—C6—C5−177.87 (16)C7—N1—S1—O1−34.88 (17)
C12—C7—C8—C91.6 (3)C7—N1—S1—C180.18 (15)
N1—C7—C8—C9178.83 (16)C6—C1—S1—O2−24.52 (19)
C12—C7—C8—C14−176.82 (18)C2—C1—S1—O2157.18 (17)
N1—C7—C8—C140.4 (3)C6—C1—S1—O1−155.40 (16)
C7—C8—C9—C10−0.3 (3)C2—C1—S1—O126.30 (19)
C14—C8—C9—C10178.10 (19)C6—C1—S1—N190.03 (18)
C7—C8—C9—C15−179.40 (18)C2—C1—S1—N1−88.26 (18)
C14—C8—C9—C15−1.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.85 (1)2.08 (1)2.8999 (19)165 (2)
Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC15H17NO2S
Mr275.36
Crystal system, space groupMonoclinic, P21/c
Temperature (K)299
a, b, c (Å)10.771 (1), 13.357 (1), 9.9667 (9)
β (°) 93.256 (8)
V (Å3)1431.6 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.22
Crystal size (mm)0.40 × 0.28 × 0.24
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.916, 0.948
No. of measured, independent and
observed [I > 2σ(I)] reflections		5990, 2924, 2283
Rint0.016
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.118, 1.05
No. of reflections2924
No. of parameters178
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.21, −0.33

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.845 (9)2.076 (11)2.8999 (19)165 (2)
Symmetry code: (i) x, −y+3/2, z−1/2.
 

References

First citationGelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2009a). Acta Cryst. E65, o366.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o15.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Foro, S., Nirmala, P. G., Terao, H. & Fuess, H. (2009b). Acta Cryst. E65, o1219.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationPerlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780–o782.  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.

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3349
https://doi.org/10.1107/S1600536810048786
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