PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o1992.
Published online 2010 July 10. doi:  10.1107/S1600536810026735
PMCID: PMC3007270

2-Methyl-N-(2-methyl­benzo­yl)benzene­sulfonamide

Abstract

In the title compound, C15H15NO3S, the 2-methyl­phenyl ring bonded to the sulfonyl group is disordered with site-occupation factors of 0.75:0.25. The dihedral angles between the two aromatic rings are 67.6 (1) and 69.2 (1)° for the major and the minor occupied sites, respectively. In the crystal, mol­ecules are linked into centrosymmetric dimers by pairs of N—H(...)O hydrogen bonds.

Related literature

For background literature and similar structures, see: Gowda et al. (2010a [triangle],b [triangle]); Suchetan et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1992-scheme1.jpg

Experimental

Crystal data

  • C15H15NO3S
  • M r = 289.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1992-efi1.jpg
  • a = 13.997 (1) Å
  • b = 14.165 (1) Å
  • c = 14.395 (2) Å
  • β = 96.955 (8)°
  • V = 2833.1 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 299 K
  • 0.40 × 0.36 × 0.34 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 [triangle]) T min = 0.912, T max = 0.925
  • 5920 measured reflections
  • 2895 independent reflections
  • 2281 reflections with I > 2σ(I)
  • R int = 0.015

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.114
  • S = 1.12
  • 2895 reflections
  • 251 parameters
  • 9 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810026735/bt5290sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026735/bt5290Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.

supplementary crystallographic information

Comment

Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts in nude mice. As part of a study of the effect of ring and the side chain substituents on the crystal structures of N-aromatic sulfonamides (Gowda et al., 2010a,b; Suchetan et al., 2010), in the present work, the structure of 2-methyl-N-(2-methylbenzoyl)benzenesulfonamide (I) has been determined (Fig.1). The conformation of the N—H bond in the S—NH—C═O segment of the structure is anti to the C═O bond, similar to that observed in 2-methyl-N-(3-methylbenzoyl)benzenesulfonamide (II) (Gowda et al., 2010a), 2-methyl-N-(4-methylbenzoyl)- benzenesulfonamide (III) (Gowda et al., 2010b) and 2-chloro-N-(2-chlorobenzoyl)benzenesulfonamide (IV) (Suchetan et al., 2010).

The conformation of the C=O bond is syn to the ortho-methyl group in the benzoyl ring, similar to that observed between the C=O bond and the ortho-Cl in (IV), but contrary to the anti conformation observed between the C=O bond and the meta-methyl group in (II).

The molecules are twisted at the S atom with the torsional angles of 57.8 (2)° (major component) and 78.6 (2)° (minor component), compared to the values of -66.2 (3)° in (II), -53.1 (2)° and 61.2 (2)° in the two molecules of (III), and 66.5 (3)° in (IV),

The dihedral angles between the sulfonyl benzene ring and the S—NH—C═O segment are 82.7 (1)° (major component) and 85.1 (3)° (minor component), compared to the values of 83.1 (1) in (II), 86.0 (1)° and 87.9 (1)° in the two molecules of (III), and 86.9 (1) in (IV)

The dihedral angle between the sulfonyl and the benzoyl benzene rings are 67.6 (1)° and 69.2 (1)° in the major and the minor components, respectively, compared to the values of 74.8 (1) in (II), 88.1 (1)° (molecule 1) and 83.5 (1)° (molecule 2) of (III), and 76.9 (1) in (IV).

The molecules are linked into chains by N—H···O(S) hydrogen bonds (Table 1 and Fig. 2).

Experimental

The title compound was prepared by refluxing a mixture of 2-methylbenzoic acid, 2-methylbenzenesulfonamide and phosphorous oxy chloride for 5 h on a water bath. The reaction mixture was cooled and poured into ice cold water. The resulting solid, 2-methyl-N-(2-methylbenzoyl)benzenesulfonamide, was separated, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried compound was recrystallized to the constant melting point.

Prism like colourless single crystals of the title compound were grown by slow evaporation of its toluene solution at room temperature.

Refinement

The H atom of the NH group was located in a difference map and restrained to N—H = 0.86 (1) %A. 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.

The methylphenyl ring with atoms C1, C2, C3, C4, C5, C6 and C14 is disordered over two sites related by a twofold rotation. The corresponding site-occupation factors were fixed to 0.75:0.25 and their corresponding bond distances in the disordered groups were restrained to be equal.

Figures

Fig. 1.
Molecular structure of (I), showing the atom labeling and displacement ellipsoids drawn at the 50% probability level. Both disorder components are shown. The minor disorder component is shown with dashed bonds.
Fig. 2.
Molecular packing of (I) with hydrogen bonding shown as dashed lines. For clarity the minor occupied disorder component was omitted.

Crystal data

C15H15NO3SF(000) = 1216
Mr = 289.34Dx = 1.357 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2699 reflections
a = 13.997 (1) Åθ = 2.6–27.8°
b = 14.165 (1) ŵ = 0.24 mm1
c = 14.395 (2) ÅT = 299 K
β = 96.955 (8)°Prism, colourless
V = 2833.1 (5) Å30.40 × 0.36 × 0.34 mm
Z = 8

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector2895 independent reflections
Radiation source: fine-focus sealed tube2281 reflections with I > 2σ(I)
graphiteRint = 0.015
Rotation method data acquisition using ω and phi scansθmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)h = −14→17
Tmin = 0.912, Tmax = 0.925k = −17→12
5920 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.12w = 1/[σ2(Fo2) + (0.0707P)2] where P = (Fo2 + 2Fc2)/3
2895 reflections(Δ/σ)max < 0.001
251 parametersΔρmax = 0.30 e Å3
9 restraintsΔρmin = −0.26 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
C1A0.1586 (2)0.3862 (2)0.2895 (2)0.0392 (7)0.75
C1B0.1568 (6)0.3398 (6)0.2942 (6)0.0354 (18)0.25
C2A0.13372 (16)0.3021 (2)0.2415 (2)0.0506 (6)0.75
C2B0.1299 (5)0.3961 (6)0.2180 (5)0.0528 (18)0.25
C3A0.0925 (6)0.3103 (4)0.1473 (4)0.0680 (17)0.75
H3A0.07260.25670.11310.082*0.75
C3B0.0951 (16)0.3438 (9)0.1388 (10)0.041 (3)0.25
H3B0.07420.37790.08490.050*0.25
C4A0.0817 (2)0.3986 (3)0.1061 (2)0.0712 (8)0.75
H4A0.05430.40290.04410.085*0.75
C4B0.0886 (6)0.2496 (8)0.1325 (6)0.066 (2)0.25
H4B0.06480.22200.07580.079*0.25
C5A0.1093 (2)0.4781 (2)0.1523 (2)0.0650 (8)0.75
H5A0.10240.53630.12230.078*0.75
C5B0.1164 (7)0.1931 (7)0.2084 (7)0.079 (3)0.25
H5B0.11330.12760.20560.095*0.25
C6A0.1483 (3)0.4725 (3)0.2459 (3)0.0505 (8)0.75
H6A0.16750.52720.27880.061*0.75
C6B0.1493 (10)0.2411 (8)0.2890 (9)0.050 (3)0.25
H6B0.16750.20620.34300.060*0.25
C70.38609 (11)0.39162 (11)0.36903 (10)0.0396 (3)
C80.47917 (10)0.33980 (11)0.37729 (10)0.0390 (3)
C90.56650 (11)0.38885 (13)0.38842 (11)0.0496 (4)
C100.65018 (12)0.33451 (18)0.39523 (14)0.0675 (6)
H100.70940.36510.40450.081*
C110.64890 (13)0.23848 (17)0.38881 (14)0.0712 (6)
H110.70640.20500.39330.085*
C120.56284 (14)0.19138 (15)0.37571 (13)0.0614 (5)
H120.56140.12600.36990.074*
C130.47861 (12)0.24202 (12)0.37119 (11)0.0479 (4)
H130.42010.21010.36390.057*
C14A0.1486 (5)0.2049 (3)0.2834 (5)0.0866 (18)0.75
H14A0.10530.19570.32950.104*0.75
H14B0.21380.19890.31240.104*0.75
H14C0.13620.15830.23510.104*0.75
C14B0.1351 (11)0.4964 (9)0.2142 (8)0.062 (3)0.25
H14D0.19190.51760.25260.074*0.25
H14E0.07920.52310.23680.074*0.25
H14F0.13760.51600.15080.074*0.25
C150.57390 (14)0.49465 (14)0.39237 (14)0.0687 (6)
H15C0.63800.51250.41760.082*
H15B0.52880.51900.43160.082*
H15A0.55960.52010.33040.082*
N10.31537 (9)0.34845 (10)0.41437 (9)0.0439 (3)
H1N0.3279 (12)0.2983 (8)0.4467 (11)0.053*
O10.15903 (8)0.32012 (10)0.46446 (9)0.0645 (4)
O20.20209 (10)0.48187 (10)0.43476 (10)0.0743 (4)
O30.36933 (9)0.46426 (9)0.32707 (9)0.0609 (4)
S10.20355 (3)0.38584 (3)0.40857 (3)0.04381 (16)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C1A0.0344 (11)0.0406 (16)0.0446 (15)0.0054 (14)0.0126 (10)0.0021 (15)
C1B0.028 (3)0.032 (5)0.046 (4)0.001 (4)0.004 (3)−0.011 (4)
C2A0.0416 (13)0.0475 (15)0.0645 (17)−0.0073 (11)0.0139 (12)−0.0012 (16)
C2B0.045 (4)0.076 (6)0.038 (4)0.008 (3)0.005 (3)0.002 (4)
C3A0.0522 (19)0.075 (5)0.078 (3)−0.018 (4)0.015 (2)−0.024 (3)
C3B0.043 (5)0.041 (8)0.038 (5)−0.008 (7)−0.003 (4)0.002 (5)
C4A0.0545 (16)0.110 (3)0.0481 (16)0.0103 (18)0.0022 (13)−0.0010 (18)
C4B0.058 (5)0.083 (7)0.057 (5)−0.022 (5)0.011 (4)−0.012 (5)
C5A0.0680 (18)0.076 (2)0.0507 (15)0.0261 (15)0.0078 (13)0.0176 (16)
C5B0.076 (6)0.065 (6)0.098 (7)−0.018 (5)0.014 (5)−0.041 (6)
C6A0.0564 (17)0.049 (2)0.047 (2)0.0174 (15)0.0092 (15)0.0061 (15)
C6B0.049 (4)0.046 (8)0.054 (5)−0.005 (6)0.004 (3)−0.012 (6)
C70.0404 (8)0.0437 (9)0.0353 (7)−0.0031 (6)0.0067 (6)0.0002 (7)
C80.0363 (8)0.0497 (9)0.0318 (7)−0.0026 (6)0.0077 (6)0.0028 (7)
C90.0449 (9)0.0658 (11)0.0392 (8)−0.0119 (8)0.0096 (7)0.0006 (8)
C100.0349 (9)0.1043 (17)0.0642 (11)−0.0074 (9)0.0089 (8)0.0060 (11)
C110.0480 (12)0.0952 (17)0.0733 (13)0.0213 (11)0.0186 (9)0.0147 (12)
C120.0604 (11)0.0623 (12)0.0648 (11)0.0151 (9)0.0214 (9)0.0044 (9)
C130.0445 (9)0.0491 (9)0.0518 (9)−0.0002 (7)0.0134 (7)0.0028 (8)
C14A0.103 (3)0.043 (3)0.118 (4)−0.016 (3)0.029 (3)−0.001 (3)
C14B0.081 (8)0.045 (7)0.058 (9)0.014 (5)0.004 (7)0.007 (6)
C150.0678 (12)0.0737 (14)0.0661 (12)−0.0303 (10)0.0151 (9)−0.0087 (10)
N10.0364 (7)0.0493 (8)0.0471 (7)0.0055 (6)0.0094 (6)0.0136 (6)
O10.0443 (7)0.0843 (9)0.0688 (8)0.0123 (6)0.0224 (6)0.0321 (7)
O20.0819 (10)0.0615 (9)0.0828 (10)0.0224 (7)0.0240 (8)−0.0093 (7)
O30.0606 (8)0.0533 (7)0.0711 (8)0.0053 (6)0.0179 (6)0.0228 (6)
S10.0401 (2)0.0535 (3)0.0392 (2)0.01159 (17)0.01069 (16)0.00625 (17)

Geometric parameters (Å, °)

C1A—C6A1.374 (4)C7—C81.488 (2)
C1A—C2A1.400 (3)C8—C131.388 (2)
C1A—S11.753 (3)C8—C91.398 (2)
C1B—C2B1.372 (10)C9—C101.395 (3)
C1B—C6B1.403 (10)C9—C151.503 (3)
C1B—S11.817 (8)C10—C111.363 (3)
C2A—C3A1.412 (7)C10—H100.9300
C2A—C14A1.507 (5)C11—C121.370 (3)
C2B—C3B1.397 (13)C11—H110.9300
C2B—C14B1.423 (13)C12—C131.375 (2)
C3A—C4A1.384 (5)C12—H120.9300
C3A—H3A0.9300C13—H130.9300
C3B—C4B1.340 (13)C14A—H14A0.9600
C3B—H3B0.9300C14A—H14B0.9600
C4A—C5A1.341 (5)C14A—H14C0.9600
C4A—H4A0.9300C14B—H14D0.9600
C4B—C5B1.372 (12)C14B—H14E0.9600
C4B—H4B0.9300C14B—H14F0.9600
C5A—C6A1.393 (4)C15—H15C0.9600
C5A—H5A0.9300C15—H15B0.9600
C5B—C6B1.375 (13)C15—H15A0.9600
C5B—H5B0.9300N1—S11.6449 (13)
C6A—H6A0.9300N1—H1N0.856 (9)
C6B—H6B0.9300O1—S11.4226 (12)
C7—O31.2018 (18)O2—S11.4123 (14)
C7—N11.3915 (19)
C6A—C1A—C2A121.7 (3)C9—C8—C7120.59 (15)
C6A—C1A—S1117.0 (3)C10—C9—C8116.66 (17)
C2A—C1A—S1121.2 (2)C10—C9—C15119.61 (16)
C2B—C1B—C6B121.7 (9)C8—C9—C15123.72 (16)
C2B—C1B—S1123.3 (7)C11—C10—C9122.80 (17)
C6B—C1B—S1115.0 (7)C11—C10—H10118.6
C1A—C2A—C3A116.9 (3)C9—C10—H10118.6
C1A—C2A—C14A124.4 (3)C10—C11—C12119.96 (17)
C3A—C2A—C14A118.7 (4)C10—C11—H11120.0
C1B—C2B—C3B112.2 (9)C12—C11—H11120.0
C1B—C2B—C14B126.9 (8)C11—C12—C13119.16 (19)
C3B—C2B—C14B120.9 (8)C11—C12—H12120.4
C4A—C3A—C2A119.8 (5)C13—C12—H12120.4
C4A—C3A—H3A120.1C12—C13—C8121.29 (17)
C2A—C3A—H3A120.1C12—C13—H13119.4
C4B—C3B—C2B126.7 (12)C8—C13—H13119.4
C4B—C3B—H3B116.6C2B—C14B—H14D109.5
C2B—C3B—H3B116.6C2B—C14B—H14E109.5
C5A—C4A—C3A122.5 (4)H14D—C14B—H14E109.5
C5A—C4A—H4A118.8C2B—C14B—H14F109.5
C3A—C4A—H4A118.8H14D—C14B—H14F109.5
C3B—C4B—C5B121.1 (9)H14E—C14B—H14F109.5
C3B—C4B—H4B119.5C9—C15—H15C109.5
C5B—C4B—H4B119.5C9—C15—H15B109.5
C4A—C5A—C6A119.2 (3)H15C—C15—H15B109.5
C4A—C5A—H5A120.4C9—C15—H15A109.5
C6A—C5A—H5A120.4H15C—C15—H15A109.5
C4B—C5B—C6B114.7 (9)H15B—C15—H15A109.5
C4B—C5B—H5B122.6C7—N1—S1124.14 (11)
C6B—C5B—H5B122.6C7—N1—H1N120.6 (12)
C1A—C6A—C5A119.9 (4)S1—N1—H1N115.2 (12)
C1A—C6A—H6A120.0O2—S1—O1117.24 (9)
C5A—C6A—H6A120.0O2—S1—N1109.94 (8)
C5B—C6B—C1B123.5 (10)O1—S1—N1103.88 (7)
C5B—C6B—H6B118.3O2—S1—C1A104.07 (11)
C1B—C6B—H6B118.3O1—S1—C1A115.14 (11)
O3—C7—N1120.35 (14)N1—S1—C1A106.11 (10)
O3—C7—C8125.34 (14)O2—S1—C1B124.9 (3)
N1—C7—C8114.30 (13)O1—S1—C1B98.2 (3)
C13—C8—C9120.09 (15)N1—S1—C1B99.6 (2)
C13—C8—C7119.29 (13)
C6A—C1A—C2A—C3A−3.5 (6)C8—C9—C10—C111.9 (3)
S1—C1A—C2A—C3A176.1 (4)C15—C9—C10—C11−177.57 (19)
C6A—C1A—C2A—C14A176.2 (4)C9—C10—C11—C12−0.4 (3)
S1—C1A—C2A—C14A−4.2 (5)C10—C11—C12—C13−1.4 (3)
C6B—C1B—C2B—C3B0.4 (16)C11—C12—C13—C81.6 (3)
S1—C1B—C2B—C3B−179.1 (12)C9—C8—C13—C12−0.1 (2)
C6B—C1B—C2B—C14B−179.3 (12)C7—C8—C13—C12178.09 (14)
S1—C1B—C2B—C14B1.2 (13)O3—C7—N1—S15.0 (2)
C1A—C2A—C3A—C4A2.3 (9)C8—C7—N1—S1−174.44 (10)
C14A—C2A—C3A—C4A−177.4 (6)C7—N1—S1—O2−54.19 (15)
C1B—C2B—C3B—C4B−1(3)C7—N1—S1—O1179.57 (13)
C14B—C2B—C3B—C4B178.4 (18)C7—N1—S1—C1A57.78 (17)
C2A—C3A—C4A—C5A0.1 (9)C7—N1—S1—C1B78.5 (3)
C2B—C3B—C4B—C5B1(3)C6A—C1A—S1—O210.4 (3)
C3A—C4A—C5A—C6A−1.5 (6)C2A—C1A—S1—O2−169.2 (2)
C3B—C4B—C5B—C6B1(2)C6A—C1A—S1—O1140.2 (2)
C2A—C1A—C6A—C5A2.2 (5)C2A—C1A—S1—O1−39.5 (3)
S1—C1A—C6A—C5A−177.4 (3)C6A—C1A—S1—N1−105.6 (3)
C4A—C5A—C6A—C1A0.3 (5)C2A—C1A—S1—N174.8 (2)
C4B—C5B—C6B—C1B−1.7 (18)C6A—C1A—S1—C1B179.8 (10)
C2B—C1B—C6B—C5B1.1 (18)C2A—C1A—S1—C1B0.2 (7)
S1—C1B—C6B—C5B−179.4 (10)C2B—C1B—S1—O211.0 (8)
O3—C7—C8—C13−139.43 (17)C6B—C1B—S1—O2−168.6 (7)
N1—C7—C8—C1339.97 (19)C2B—C1B—S1—O1142.7 (6)
O3—C7—C8—C938.8 (2)C6B—C1B—S1—O1−36.9 (8)
N1—C7—C8—C9−141.84 (14)C2B—C1B—S1—N1−111.7 (7)
C13—C8—C9—C10−1.6 (2)C6B—C1B—S1—N168.8 (8)
C7—C8—C9—C10−179.76 (14)C2B—C1B—S1—C1A−1.6 (5)
C13—C8—C9—C15177.84 (16)C6B—C1B—S1—C1A178.9 (14)
C7—C8—C9—C15−0.3 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.86 (1)2.10 (1)2.9531 (17)172 (2)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5290).

References

  • Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010a). Acta Cryst. E66, o433. [PMC free article] [PubMed]
  • Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010b). Acta Cryst. E66, o747. [PMC free article] [PubMed]
  • Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Yarnton, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1040. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography