N-(3,5-Dimethyl­phen­yl)benzene­sulfonamide

Nirmala, P.G.; Gowda, B.T.; Foro, S.; Fuess, H.

doi:10.1107/S1600536809050089

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3225

doi:10.1107/S1600536809050089

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N-(3,5-Dimethylphenyl)benzenesulfonamide

P. G. Nirmala,^a B. Thimme Gowda,^a ^* Sabine Foro ^b and Hartmut Fuess ^b

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

(Received 15 November 2009; accepted 21 November 2009; online 28 November 2009)

In the crystal structure of the title compound, C₁₄H₁₅NO₂S, the molecule is bent at the S atom with a C—SO₂—NH—C torsion angle of 67.9 (2)°. The two benzene rings are tilted by 54.6 (1)° relative to each other. In the crystal, intermolecular N—H⋯O hydrogen bonds pack the molecules into a supramolecular structure.

Related literature

For preparation of the title compound, see: Gowda et al. (2005 ). For our study of the effects of substituents on the structures of N-(aryl)-arylsulfonamides, see: Gowda et al. (2008 ; 2009a ,b ). For related structures, see: Gelbrich et al. (2007 ); Perlovich et al. (2006 ).

Experimental

Crystal data

C₁₄H₁₅NO₂S
M_r = 261.33
Monoclinic, P 2₁ /c
a = 11.192 (1) Å
b = 7.3543 (7) Å
c = 16.672 (2) Å
β = 101.62 (1)°
V = 1344.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 299 K
0.48 × 0.40 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.896, T_max = 0.959
5063 measured reflections
2742 independent reflections
2187 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.111
S = 1.05
2742 reflections
169 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.81 (2)	2.14 (2)	2.942 (2)	176 (2)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050089/bx2251sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050089/bx2251Isup2.hkl

checkCIF report

Comment top

As part of a study of substituent effects on the structures of N-(aryl)-arylsulfonamides (Gowda et al., 2008; 2009a,b), in the present work, the structure of N-(3,5-dimethylphenyl)benzenesulfonamide (I) has been determined (Fig. 1). The molecule is bent at the S atom with the C1—SO₂—NH—C7 torsion angle of 67.9 (2)°, compared to the values of 71.0 (2)° in N-(2,3-dimethylphenyl)benzenesulfonamide (II)(Gowda et al., 2009a), 62.7 (2)° in N-(2,5-dimethylphenyl)benzenesulfonamide (III) (Gowda et al., 2009b) and -78.7 (2)° in N-(2,6-dimethylphenyl)benzenesulfonamide (IV)(Gowda et al., 2008). The two benzene rings in (I) are tilted relative to each other by 54.6 (1)°, compared to the values of 64.8 (1)° in (II), 40.4 (1)° in (III) and 44.9 (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 crystal packing of molecules in (I) via N—H···O(S) hydrogen bonds (Table 1) is shown in Fig.2.

Related literature top

For preparation of the title compound, see: Gowda et al. (2005). For our study of the effects of substituents on the structures of N-(aryl)-arylsulfonamides, see: Gowda et al. (2008; 2009a,b). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006)

Experimental top

The solution of benzene (10 cc) in chloroform (40 cc) was treated dropwise with chlorosulfonic acid (25 cc) 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 3,5-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 cc). The resultant solid N-(3,5-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.

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

	Fig. 1. Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

N-(3,5-Dimethylphenyl)benzenesulfonamide top

Crystal data top

C₁₄H₁₅NO₂S	F(000) = 552
M_r = 261.33	D_x = 1.291 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.192 (1) Å	θ = 2.5–27.8°
b = 7.3543 (7) Å	µ = 0.23 mm⁻¹
c = 16.672 (2) Å	T = 299 K
β = 101.62 (1)°	Prism, colourless
V = 1344.1 (2) Å³	0.48 × 0.40 × 0.18 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2742 independent reflections
Radiation source: fine-focus sealed tube	2187 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
Rotation method data acquisition using ω and phi scans	θ_max = 26.4°, θ_min = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→13
T_min = 0.896, T_max = 0.959	k = −6→9
5063 measured reflections	l = −9→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0575P)² + 0.3783P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.004
2742 reflections	Δρ_max = 0.31 e Å⁻³
169 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0115 (18)

Crystal data top

C₁₄H₁₅NO₂S	V = 1344.1 (2) Å³
M_r = 261.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.192 (1) Å	µ = 0.23 mm⁻¹
b = 7.3543 (7) Å	T = 299 K
c = 16.672 (2) Å	0.48 × 0.40 × 0.18 mm
β = 101.62 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2742 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2187 reflections with I > 2σ(I)
T_min = 0.896, T_max = 0.959	R_int = 0.015
5063 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.31 e Å⁻³
2742 reflections	Δρ_min = −0.31 e Å⁻³
169 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

	x	y	z	U_iso*/U_eq
C1	0.41245 (16)	0.1889 (3)	0.59746 (11)	0.0434 (4)
C2	0.52681 (19)	0.2478 (3)	0.59053 (14)	0.0618 (6)
H2	0.5873	0.2668	0.6369	0.074*
C3	0.5495 (3)	0.2780 (4)	0.51321 (17)	0.0816 (8)
H3	0.6266	0.3161	0.5074	0.098*
C4	0.4597 (3)	0.2524 (4)	0.44490 (15)	0.0790 (8)
H4	0.4764	0.2716	0.3931	0.095*
C5	0.3458 (3)	0.1986 (4)	0.45274 (14)	0.0805 (8)
H5	0.2846	0.1846	0.4063	0.097*
C6	0.3209 (2)	0.1650 (3)	0.52926 (13)	0.0620 (6)
H6	0.2438	0.1268	0.5347	0.074*
C7	0.20322 (14)	0.3865 (2)	0.68610 (10)	0.0354 (4)
C8	0.18940 (16)	0.5491 (2)	0.64340 (10)	0.0410 (4)
H8	0.2578	0.6162	0.6381	0.049*
C9	0.07428 (18)	0.6121 (3)	0.60856 (12)	0.0479 (5)
C10	−0.02579 (17)	0.5069 (3)	0.61670 (12)	0.0514 (5)
H10	−0.1035	0.5477	0.5929	0.062*
C11	−0.01416 (16)	0.3444 (3)	0.65873 (12)	0.0489 (5)
C12	0.10215 (16)	0.2850 (3)	0.69465 (11)	0.0430 (4)
H12	0.1122	0.1772	0.7244	0.052*
C13	0.0577 (2)	0.7909 (3)	0.56388 (16)	0.0733 (7)
H13A	0.1323	0.8239	0.5476	0.088*
H13B	0.0364	0.8830	0.5993	0.088*
H13C	−0.0063	0.7799	0.5162	0.088*
C14	−0.12452 (19)	0.2338 (4)	0.66755 (16)	0.0755 (7)
H14A	−0.1717	0.2058	0.6142	0.091*
H14B	−0.1735	0.3023	0.6978	0.091*
H14C	−0.0985	0.1229	0.6962	0.091*
N1	0.32271 (13)	0.3272 (2)	0.72571 (9)	0.0395 (4)
H1N	0.3739 (18)	0.406 (3)	0.7338 (12)	0.047*
O1	0.49861 (12)	0.12569 (19)	0.75071 (8)	0.0526 (4)
O2	0.29563 (13)	0.00239 (19)	0.68847 (10)	0.0590 (4)
S1	0.38310 (4)	0.14444 (6)	0.69537 (3)	0.04071 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0437 (10)	0.0417 (10)	0.0431 (9)	0.0098 (8)	0.0043 (8)	−0.0040 (8)
C2	0.0500 (12)	0.0781 (15)	0.0577 (13)	0.0046 (11)	0.0119 (10)	0.0035 (11)
C3	0.0782 (18)	0.100 (2)	0.0758 (17)	0.0074 (16)	0.0366 (14)	0.0110 (16)
C4	0.110 (2)	0.0806 (18)	0.0512 (14)	0.0199 (16)	0.0283 (15)	0.0035 (12)
C5	0.104 (2)	0.0826 (18)	0.0466 (13)	0.0137 (16)	−0.0035 (13)	−0.0090 (12)
C6	0.0616 (14)	0.0681 (14)	0.0509 (12)	0.0016 (11)	−0.0019 (10)	−0.0081 (10)
C7	0.0323 (8)	0.0407 (9)	0.0330 (8)	0.0014 (7)	0.0063 (6)	−0.0033 (7)
C8	0.0411 (9)	0.0395 (9)	0.0419 (9)	−0.0038 (8)	0.0074 (7)	−0.0010 (7)
C9	0.0507 (11)	0.0427 (10)	0.0458 (10)	0.0040 (8)	−0.0008 (8)	−0.0007 (8)
C10	0.0365 (10)	0.0596 (12)	0.0539 (11)	0.0079 (9)	−0.0012 (8)	−0.0014 (10)
C11	0.0354 (9)	0.0621 (12)	0.0495 (11)	−0.0036 (8)	0.0093 (8)	0.0006 (9)
C12	0.0393 (9)	0.0463 (10)	0.0441 (10)	−0.0018 (8)	0.0101 (7)	0.0058 (8)
C13	0.0773 (16)	0.0504 (13)	0.0804 (17)	0.0035 (12)	−0.0119 (13)	0.0119 (12)
C14	0.0411 (12)	0.100 (2)	0.0858 (17)	−0.0124 (12)	0.0142 (11)	0.0160 (15)
N1	0.0326 (8)	0.0392 (8)	0.0450 (8)	−0.0012 (6)	0.0038 (6)	−0.0030 (6)
O1	0.0436 (7)	0.0577 (8)	0.0510 (7)	0.0142 (6)	−0.0032 (6)	0.0062 (6)
O2	0.0556 (8)	0.0410 (7)	0.0798 (10)	−0.0062 (6)	0.0123 (7)	−0.0002 (7)
S1	0.0367 (3)	0.0373 (3)	0.0457 (3)	0.00433 (18)	0.00246 (18)	0.00225 (18)

Geometric parameters (Å, º) top

C1—C2	1.378 (3)	C9—C10	1.390 (3)
C1—C6	1.380 (3)	C9—C13	1.505 (3)
C1—S1	1.7594 (19)	C10—C11	1.378 (3)
C2—C3	1.381 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.389 (2)
C3—C4	1.372 (4)	C11—C14	1.511 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.366 (4)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—C6	1.382 (3)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C8	1.384 (2)	C14—H14C	0.9600
C7—C12	1.386 (2)	N1—S1	1.6302 (15)
C7—N1	1.435 (2)	N1—H1N	0.81 (2)
C8—C9	1.382 (2)	O1—S1	1.4356 (13)
C8—H8	0.9300	O2—S1	1.4204 (14)

C2—C1—C6	121.3 (2)	C9—C10—H10	118.8
C2—C1—S1	119.10 (15)	C10—C11—C12	118.44 (17)
C6—C1—S1	119.64 (16)	C10—C11—C14	121.40 (19)
C1—C2—C3	118.5 (2)	C12—C11—C14	120.15 (19)
C1—C2—H2	120.7	C7—C12—C11	119.97 (17)
C3—C2—H2	120.7	C7—C12—H12	120.0
C4—C3—C2	120.7 (2)	C11—C12—H12	120.0
C4—C3—H3	119.6	C9—C13—H13A	109.5
C2—C3—H3	119.6	C9—C13—H13B	109.5
C5—C4—C3	120.2 (2)	H13A—C13—H13B	109.5
C5—C4—H4	119.9	C9—C13—H13C	109.5
C3—C4—H4	119.9	H13A—C13—H13C	109.5
C4—C5—C6	120.4 (2)	H13B—C13—H13C	109.5
C4—C5—H5	119.8	C11—C14—H14A	109.5
C6—C5—H5	119.8	C11—C14—H14B	109.5
C1—C6—C5	118.9 (2)	H14A—C14—H14B	109.5
C1—C6—H6	120.5	C11—C14—H14C	109.5
C5—C6—H6	120.5	H14A—C14—H14C	109.5
C8—C7—C12	120.60 (16)	H14B—C14—H14C	109.5
C8—C7—N1	119.75 (15)	C7—N1—S1	120.92 (12)
C12—C7—N1	119.56 (16)	C7—N1—H1N	115.0 (15)
C9—C8—C7	120.24 (16)	S1—N1—H1N	108.7 (15)
C9—C8—H8	119.9	O2—S1—O1	119.88 (9)
C7—C8—H8	119.9	O2—S1—N1	108.03 (8)
C8—C9—C10	118.28 (18)	O1—S1—N1	104.82 (8)
C8—C9—C13	120.85 (19)	O2—S1—C1	108.42 (9)
C10—C9—C13	120.87 (18)	O1—S1—C1	107.56 (9)
C11—C10—C9	122.46 (17)	N1—S1—C1	107.53 (8)
C11—C10—H10	118.8

C6—C1—C2—C3	−1.8 (3)	C8—C7—C12—C11	1.4 (3)
S1—C1—C2—C3	178.45 (19)	N1—C7—C12—C11	177.90 (16)
C1—C2—C3—C4	0.9 (4)	C10—C11—C12—C7	−1.5 (3)
C2—C3—C4—C5	0.8 (4)	C14—C11—C12—C7	179.70 (19)
C3—C4—C5—C6	−1.7 (4)	C8—C7—N1—S1	−114.44 (16)
C2—C1—C6—C5	0.9 (3)	C12—C7—N1—S1	69.0 (2)
S1—C1—C6—C5	−179.33 (19)	C7—N1—S1—O2	−48.89 (16)
C4—C5—C6—C1	0.9 (4)	C7—N1—S1—O1	−177.81 (13)
C12—C7—C8—C9	−0.1 (3)	C7—N1—S1—C1	67.93 (15)
N1—C7—C8—C9	−176.67 (16)	C2—C1—S1—O2	−148.57 (17)
C7—C8—C9—C10	−0.9 (3)	C6—C1—S1—O2	31.65 (19)
C7—C8—C9—C13	178.38 (19)	C2—C1—S1—O1	−17.56 (19)
C8—C9—C10—C11	0.7 (3)	C6—C1—S1—O1	162.66 (16)
C13—C9—C10—C11	−178.5 (2)	C2—C1—S1—N1	94.86 (17)
C9—C10—C11—C12	0.5 (3)	C6—C1—S1—N1	−84.93 (18)
C9—C10—C11—C14	179.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.81 (2)	2.14 (2)	2.942 (2)	176 (2)

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅NO₂S
M_r	261.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	11.192 (1), 7.3543 (7), 16.672 (2)
β (°)	101.62 (1)
V (Å³)	1344.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.48 × 0.40 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.896, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	5063, 2742, 2187
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.111, 1.05
No. of reflections	2742
No. of parameters	169
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.31

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···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.81 (2)	2.14 (2)	2.942 (2)	176 (2)

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

References

Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1691. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 65| Part 12| December 2009| Page o3225

doi:10.1107/S1600536809050089

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