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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 65| Part 11| November 2009| Page o2763
https://doi.org/10.1107/S1600536809041841

N-(2,5-Di­methyl­phen­yl)benzene­sulfonamide

B. Thimme Gowda,a* Sabine Foro,b P. G. Nirmalaa and Hartmut Fuessb

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287, Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 9 October 2009; accepted 13 October 2009; online 17 October 2009)

In the title compound, C14H15NO2S, the dihedral angle between the aromatic rings is 40.4 (1)° relative to each other. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur.

Related literature

For the preparation of the title compound, see: Gowda et al. (2005[Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.]). For related structures, see: Gowda et al. (2008a[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64, o1691.],b[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1692.]; 2009[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2009). Acta Cryst. E65, o366.]). For bond-length data for other aryl sulfonamides, 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

  • C14H15NO2S

  • Mr = 261.33

  • Monoclinic, P 21 /n

  • a = 10.523 (1) Å

  • b = 8.5631 (7) Å

  • c = 15.135 (2) Å

  • β = 101.86 (1)°

  • V = 1334.7 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 299 K

  • 0.44 × 0.40 × 0.34 mm
Data collection

  • Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.903, Tmax = 0.924

  • 5236 measured reflections

  • 2727 independent reflections

  • 2221 reflections with I > 2σ(I)

  • Rint = 0.010
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.108

  • S = 1.10

  • 2727 reflections

  • 169 parameters

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

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O1i 0.828 (19) 2.16 (2) 2.9634 (19) 163.3 (19)
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, 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/S1600536809041841/pk2200sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041841/pk2200Isup2.hkl

checkCIF report


Comment top

In the present work, as part of a study of substituent effects on the structures of N-(aryl)-arylsulfonamides, the structure of N-(2,5-dimethylphenyl)benzenesulfonamide (I) has been determined (Gowda et al., 2008a, 2008b, 2009). The conformation of the N—C bond in the C—SO2—NH—C segment has gauche torsions with the S=O bonds (Fig. 1). The molecule is bent at the S atom with the C—SO2—NH—C torsion angle of 62.7 (2)°. The two benzene rings in (I) are tilted relative to each other by 40.4 (1)°, compared to the values of 61.5 (1)° in N-(2-methylphenyl)benzenesulfonamide (II) (Gowda et al., 2008b), 64.8 (1)° in N-(2,3-dimethylphenyl)- benzenesulfonamide (III) (Gowda et al., 2009) and 44.9 (1)° in N-(2,6-dimethylphenyl)benzenesulfonamide (IV) (Gowda et al., 2008a). The other bond parameters are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The crystal packing of (I) showing dimers linked via N—H···O(S) hydrogen bonds (Table 1) is given in Fig.2.

Related literature top

For the preparation of the title compound, see: Gowda et al. (2005). For related structures, see: Gowda et al. (2008a,b; 2009). For bond-length data for other aryl sulfonamides, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Experimental top

A solution of benzene (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 benzenesulfonylchloride was treated with 2,5-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 solid N-(2,5-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 (Gowda et al., 2005). The 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 its position refined with N—H = 0.83 (2) %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).

Structure description top

In the present work, as part of a study of substituent effects on the structures of N-(aryl)-arylsulfonamides, the structure of N-(2,5-dimethylphenyl)benzenesulfonamide (I) has been determined (Gowda et al., 2008a, 2008b, 2009). The conformation of the N—C bond in the C—SO2—NH—C segment has gauche torsions with the S=O bonds (Fig. 1). The molecule is bent at the S atom with the C—SO2—NH—C torsion angle of 62.7 (2)°. The two benzene rings in (I) are tilted relative to each other by 40.4 (1)°, compared to the values of 61.5 (1)° in N-(2-methylphenyl)benzenesulfonamide (II) (Gowda et al., 2008b), 64.8 (1)° in N-(2,3-dimethylphenyl)- benzenesulfonamide (III) (Gowda et al., 2009) and 44.9 (1)° in N-(2,6-dimethylphenyl)benzenesulfonamide (IV) (Gowda et al., 2008a). The other bond parameters are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The crystal packing of (I) showing dimers linked via N—H···O(S) hydrogen bonds (Table 1) is given in Fig.2.

For the preparation of the title compound, see: Gowda et al. (2005). For related structures, see: Gowda et al. (2008a,b; 2009). For bond-length data for other aryl sulfonamides, 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 labelling 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, viewed down the b axis.
N-(2,5-Dimethylphenyl)benzenesulfonamide top
Crystal data top
C14H15NO2SF(000) = 552
Mr = 261.33Dx = 1.301 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2374 reflections
a = 10.523 (1) Åθ = 2.6–27.8°
b = 8.5631 (7) ŵ = 0.24 mm−1
c = 15.135 (2) ÅT = 299 K
β = 101.86 (1)°Prism, colourless
V = 1334.7 (2) Å30.44 × 0.40 × 0.34 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur (TM) Single Crystal X-ray Diffractometer with Sapphire CCD Detector.2727 independent reflections
Radiation source: fine-focus sealed tube2221 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.010
Detector resolution: 0 pixels mm-1θmax = 26.4°, θmin = 2.6°
Rotation method data acquisition using ω and phi scans.h = −10→13
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		k = −10→7
Tmin = 0.903, Tmax = 0.924l = −17→18
5236 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)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0568P)2 + 0.2974P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
2727 reflectionsΔρmax = 0.27 e Å−3
169 parametersΔρmin = −0.26 e Å−3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0149 (18)
Crystal data top
C14H15NO2SV = 1334.7 (2) Å3
Mr = 261.33Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.523 (1) ŵ = 0.24 mm−1
b = 8.5631 (7) ÅT = 299 K
c = 15.135 (2) Å0.44 × 0.40 × 0.34 mm
β = 101.86 (1)°
Data collection top
Oxford Diffraction Xcalibur (TM) Single Crystal X-ray Diffractometer with Sapphire CCD Detector.2727 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		2221 reflections with I > 2σ(I)
Tmin = 0.903, Tmax = 0.924Rint = 0.010
5236 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.27 e Å−3
2727 reflectionsΔρmin = −0.26 e Å−3
169 parameters
Special details top

Experimental. 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
S10.78193 (4)0.44572 (5)−0.00630 (3)0.03753 (16)
O10.88777 (11)0.35489 (14)−0.02510 (9)0.0504 (3)
O20.68808 (12)0.37259 (15)0.03523 (9)0.0476 (3)
N10.84891 (13)0.58790 (18)0.05948 (10)0.0417 (4)
H1N0.9148 (19)0.619 (2)0.0428 (13)0.050*
C10.70021 (15)0.53338 (19)−0.10743 (11)0.0381 (4)
C20.57570 (16)0.5897 (2)−0.11257 (13)0.0474 (4)
H20.53350.5753−0.06490.057*
C30.5152 (2)0.6672 (3)−0.18942 (16)0.0647 (6)
H30.43150.7057−0.19370.078*
C40.5778 (2)0.6880 (3)−0.25983 (16)0.0722 (7)
H40.53610.7404−0.31150.087*
C50.7015 (2)0.6322 (3)−0.25444 (14)0.0672 (6)
H50.74290.6467−0.30250.081*
C60.76449 (19)0.5545 (2)−0.17803 (13)0.0513 (5)
H60.84840.5170−0.17390.062*
C70.76772 (16)0.7043 (2)0.08868 (12)0.0437 (4)
C80.7529 (2)0.8517 (2)0.04985 (15)0.0607 (5)
C90.6695 (3)0.9543 (3)0.0839 (2)0.0831 (8)
H90.65501.05380.05930.100*
C100.6091 (3)0.9108 (3)0.1524 (2)0.0825 (8)
H100.55400.98150.17220.099*
C110.62731 (19)0.7668 (3)0.19244 (15)0.0622 (6)
C120.70773 (16)0.6642 (2)0.15926 (13)0.0486 (4)
H120.72210.56550.18490.058*
C130.8207 (3)0.9011 (3)−0.0238 (2)0.0899 (8)
H13A0.90910.8655−0.00990.108*
H13B0.81931.0129−0.02850.108*
H13C0.77710.8565−0.08010.108*
C140.5648 (2)0.7236 (4)0.27002 (18)0.0873 (9)
H14A0.56220.81360.30740.105*
H14B0.61430.64250.30500.105*
H14C0.47800.68730.24710.105*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0331 (2)0.0359 (2)0.0443 (3)0.00200 (16)0.00952 (16)0.00318 (17)
O10.0408 (7)0.0461 (7)0.0665 (8)0.0092 (5)0.0160 (6)0.0016 (6)
O20.0451 (7)0.0453 (7)0.0557 (7)−0.0032 (5)0.0178 (6)0.0076 (6)
N10.0323 (7)0.0464 (8)0.0455 (8)−0.0026 (6)0.0059 (6)0.0000 (6)
C10.0367 (8)0.0365 (9)0.0401 (9)−0.0039 (7)0.0057 (6)−0.0013 (7)
C20.0361 (9)0.0486 (10)0.0563 (11)−0.0009 (8)0.0065 (7)0.0057 (8)
C30.0464 (11)0.0637 (13)0.0759 (15)−0.0004 (10)−0.0062 (10)0.0161 (11)
C40.0747 (15)0.0708 (15)0.0588 (13)−0.0115 (12)−0.0145 (11)0.0211 (11)
C50.0848 (16)0.0733 (15)0.0435 (11)−0.0153 (13)0.0134 (10)0.0075 (10)
C60.0522 (10)0.0533 (11)0.0513 (11)−0.0013 (9)0.0174 (8)0.0003 (9)
C70.0362 (8)0.0413 (9)0.0479 (10)−0.0017 (7)−0.0048 (7)−0.0071 (8)
C80.0646 (13)0.0414 (10)0.0685 (14)−0.0071 (9)−0.0041 (10)−0.0037 (9)
C90.0940 (19)0.0369 (11)0.105 (2)0.0072 (12)−0.0096 (16)−0.0086 (12)
C100.0697 (15)0.0679 (16)0.106 (2)0.0097 (13)0.0097 (14)−0.0323 (15)
C110.0484 (11)0.0638 (14)0.0715 (14)−0.0028 (10)0.0057 (9)−0.0311 (11)
C120.0402 (9)0.0514 (11)0.0507 (10)−0.0020 (8)0.0016 (7)−0.0129 (8)
C130.113 (2)0.0534 (14)0.097 (2)−0.0199 (15)0.0091 (16)0.0187 (13)
C140.0714 (15)0.109 (2)0.0881 (18)−0.0067 (15)0.0315 (13)−0.0484 (16)
Geometric parameters (Å, º) top
S1—O21.4205 (12)C7—C81.387 (3)
S1—O11.4340 (12)C7—C121.391 (3)
S1—N11.6377 (15)C8—C91.412 (3)
S1—C11.7620 (17)C8—C131.503 (4)
N1—C71.440 (2)C9—C101.374 (4)
N1—H1N0.828 (19)C9—H90.9300
C1—C21.383 (2)C10—C111.370 (4)
C1—C61.389 (2)C10—H100.9300
C2—C31.376 (3)C11—C121.384 (3)
C2—H20.9300C11—C141.505 (3)
C3—C41.375 (3)C12—H120.9300
C3—H30.9300C13—H13A0.9600
C4—C51.373 (3)C13—H13B0.9600
C4—H40.9300C13—H13C0.9600
C5—C61.380 (3)C14—H14A0.9600
C5—H50.9300C14—H14B0.9600
C6—H60.9300C14—H14C0.9600
O2—S1—O1119.19 (8)C12—C7—N1117.14 (16)
O2—S1—N1108.07 (8)C7—C8—C9115.8 (2)
O1—S1—N1105.61 (8)C7—C8—C13122.8 (2)
O2—S1—C1108.22 (8)C9—C8—C13121.4 (2)
O1—S1—C1108.61 (8)C10—C9—C8121.7 (2)
N1—S1—C1106.47 (8)C10—C9—H9119.2
C7—N1—S1119.53 (11)C8—C9—H9119.2
C7—N1—H1N117.4 (15)C11—C10—C9122.3 (2)
S1—N1—H1N109.5 (14)C11—C10—H10118.9
C2—C1—C6121.13 (16)C9—C10—H10118.9
C2—C1—S1119.01 (13)C10—C11—C12116.8 (2)
C6—C1—S1119.72 (13)C10—C11—C14121.5 (2)
C3—C2—C1118.92 (18)C12—C11—C14121.7 (2)
C3—C2—H2120.5C11—C12—C7122.0 (2)
C1—C2—H2120.5C11—C12—H12119.0
C4—C3—C2120.4 (2)C7—C12—H12119.0
C4—C3—H3119.8C8—C13—H13A109.5
C2—C3—H3119.8C8—C13—H13B109.5
C5—C4—C3120.5 (2)H13A—C13—H13B109.5
C5—C4—H4119.7C8—C13—H13C109.5
C3—C4—H4119.7H13A—C13—H13C109.5
C4—C5—C6120.3 (2)H13B—C13—H13C109.5
C4—C5—H5119.9C11—C14—H14A109.5
C6—C5—H5119.9C11—C14—H14B109.5
C5—C6—C1118.76 (19)H14A—C14—H14B109.5
C5—C6—H6120.6C11—C14—H14C109.5
C1—C6—H6120.6H14A—C14—H14C109.5
C8—C7—C12121.37 (18)H14B—C14—H14C109.5
C8—C7—N1121.47 (18)
O2—S1—N1—C7−53.36 (15)S1—C1—C6—C5−175.98 (16)
O1—S1—N1—C7178.05 (13)S1—N1—C7—C8−102.82 (18)
C1—S1—N1—C762.70 (15)S1—N1—C7—C1278.98 (18)
O2—S1—C1—C231.30 (16)C12—C7—C8—C9−2.6 (3)
O1—S1—C1—C2162.03 (14)N1—C7—C8—C9179.28 (17)
N1—S1—C1—C2−84.66 (15)C12—C7—C8—C13177.4 (2)
O2—S1—C1—C6−153.10 (14)N1—C7—C8—C13−0.8 (3)
O1—S1—C1—C6−22.37 (16)C7—C8—C9—C101.2 (3)
N1—S1—C1—C690.94 (15)C13—C8—C9—C10−178.8 (2)
C6—C1—C2—C30.2 (3)C8—C9—C10—C110.8 (4)
S1—C1—C2—C3175.78 (15)C9—C10—C11—C12−1.5 (3)
C1—C2—C3—C40.1 (3)C9—C10—C11—C14177.4 (2)
C2—C3—C4—C5−0.1 (4)C10—C11—C12—C70.0 (3)
C3—C4—C5—C6−0.1 (4)C14—C11—C12—C7−178.80 (18)
C4—C5—C6—C10.4 (3)C8—C7—C12—C112.1 (3)
C2—C1—C6—C5−0.5 (3)N1—C7—C12—C11−179.74 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.828 (19)2.16 (2)2.9634 (19)163.3 (19)
Symmetry code: (i) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formulaC14H15NO2S
Mr261.33
Crystal system, space groupMonoclinic, P21/n
Temperature (K)299
a, b, c (Å)10.523 (1), 8.5631 (7), 15.135 (2)
β (°) 101.86 (1)
V (Å3)1334.7 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.24
Crystal size (mm)0.44 × 0.40 × 0.34
Data collection
DiffractometerOxford Diffraction Xcalibur (TM) Single Crystal X-ray Diffractometer with Sapphire CCD Detector.
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.903, 0.924
No. of measured, independent and
observed [I > 2σ(I)] reflections		5236, 2727, 2221
Rint0.010
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.108, 1.10
No. of reflections2727
No. of parameters169
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.27, −0.26

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (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···O1i0.828 (19)2.16 (2)2.9634 (19)163.3 (19)
Symmetry code: (i) −x+2, −y+1, −z.
 

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for an extension of his research fellowship.

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
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ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page o2763
https://doi.org/10.1107/S1600536809041841
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