2,4-Dimethyl-N-(3-methyl­phen­yl)benzene­sulfonamide

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

doi:10.1107/S1600536810011529

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o989

doi:10.1107/S1600536810011529

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2,4-Dimethyl-N-(3-methylphenyl)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 20 March 2010; accepted 26 March 2010; online 31 March 2010)

In the structure of the title compound, C₁₅H₁₇NO₂S, the dihedral angle between the two aromatic rings is 47.1 (1)°. In the crystal structure, molecules are connected by N—H⋯O hydrogen bonds, forming C(4) chains running along the c axis.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009 , 2010 ); Nirmala et al. (2009 ). For related structures, see: Gelbrich et al. (2007 ); Perlovich et al. (2006 ).

Experimental

Crystal data

C₁₅H₁₇NO₂S
M_r = 275.36
Monoclinic, P 2₁ /c
a = 9.110 (1) Å
b = 15.367 (2) Å
c = 10.422 (1) Å
β = 104.05 (1)°
V = 1415.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 299 K
0.40 × 0.40 × 0.26 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 = 0.915, T_max = 0.944
5538 measured reflections
2870 independent reflections
2375 reflections with I > 2σ(I)
R_int = 0.012

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.112
S = 1.06
2870 reflections
178 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.83 (2)	2.13 (3)	2.932 (2)	162 (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 ); 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/S1600536810011529/bt5222sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810011529/bt5222Isup2.hkl

checkCIF report

Comment top

As part of a study of the effect of substitutions on the structures of N-(aryl)-arylsulfonamides (Gowda et al., 2009; Gowda et al., 2010; Nirmala et al., 2009), in the present work, the structure of 2,4-dimethyl-N-(3-methylphenyl)benzenesulfonamide (I) has been determined (Fig. 1). The conformation of the N—C bond in the C—SO₂—NH—C segment has gauche torsions with respect to the S═O bonds. The molecule is twisted at the S—N bond with the C1—SO₂—NH—C7 torsion angle of -58.4 (2)°, compared to the values of 71.6 (1)° in 2,4-dimethyl-N-(3-methylphenyl)benzenesulfonamide (II)(Nirmala et al., 2009), -46.1 (3)° (molecule 1) & 47.7 (3)° (molecule 2) in the two molecules of 2,4-dimethyl-N-(phenyl)- benzenesulfonamide (III)(Gowda et al., 2009) and 55.8 (2)° and -58.4 (3)°, respectively, in the 2 molecules of N- (3-methylphenyl)benzenesulfonamide (IV)(Gowda et al., 2010). The conformation of the N—H bond in (I) is anti to the 3-methyl group in the aniline benzene ring, compared the syn conformation observed between the N—H bond and the 3-methyl group in (IV).

The sulfonyl benzene and the aniline benzene rings in (I) are tilted relative to each other by 47.1 (1)°, compared to the values of 47.0 (1)° in (II), 67.5 (1)° in molecule 1 and 72.9 (1)° in molecule 2 of (III), and 67.9 (1)° in molecule 1 and 68.6 (1)° in molecule 2 of (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 shows that the molecules are connected by N—H···O hydrogen bonds (Table 1) to chains running along the c axis (Fig. 2).

Related literature top

For the preparation of the title compound, see: Savitha & Gowda (2006). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009, 2010); Nirmala et al. (2009). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Experimental top

The solution of 1,3-xylene (1,3-dimethylbenzene) (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 2,4-dimethylbenzenesulfonylchloride was treated with m-toluidine 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 2,4-dimethyl-N-(3-methylphenyl)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 (Savitha & Gowda, 2006). The prism like colourless 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 the title compound, showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

2,4-Dimethyl-N-(3-methylphenyl)benzenesulfonamide top

Crystal data top

C₁₅H₁₇NO₂S	F(000) = 584
M_r = 275.36	D_x = 1.292 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3146 reflections
a = 9.110 (1) Å	θ = 2.6–27.7°
b = 15.367 (2) Å	µ = 0.23 mm⁻¹
c = 10.422 (1) Å	T = 299 K
β = 104.05 (1)°	Prism, colourless
V = 1415.4 (3) Å³	0.40 × 0.40 × 0.26 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2870 independent reflections
Radiation source: fine-focus sealed tube	2375 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
Rotation method data acquisition using ω and phi scans	θ_max = 26.4°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→9
T_min = 0.915, T_max = 0.944	k = −19→14
5538 measured reflections	l = −13→10

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0485P)² + 0.8232P] where P = (F_o² + 2F_c²)/3
2870 reflections	(Δ/σ)_max = 0.014
178 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₅H₁₇NO₂S	V = 1415.4 (3) Å³
M_r = 275.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.110 (1) Å	µ = 0.23 mm⁻¹
b = 15.367 (2) Å	T = 299 K
c = 10.422 (1) Å	0.40 × 0.40 × 0.26 mm
β = 104.05 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2870 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2375 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.944	R_int = 0.012
5538 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.23 e Å⁻³
2870 reflections	Δρ_min = −0.34 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.4436 (2)	0.60399 (12)	0.09959 (19)	0.0371 (4)
C2	0.4722 (2)	0.55232 (13)	0.2140 (2)	0.0411 (4)
C3	0.3789 (2)	0.48048 (14)	0.2118 (2)	0.0492 (5)
H3	0.3962	0.4450	0.2863	0.059*
C4	0.2619 (2)	0.45894 (14)	0.1049 (3)	0.0522 (6)
C5	0.2385 (3)	0.51066 (16)	−0.0060 (2)	0.0567 (6)
H5	0.1616	0.4968	−0.0797	0.068*
C6	0.3279 (2)	0.58303 (15)	−0.0092 (2)	0.0491 (5)
H6	0.3103	0.6177	−0.0846	0.059*
C7	0.3096 (2)	0.79578 (12)	0.12108 (18)	0.0361 (4)
C8	0.2602 (2)	0.84940 (13)	0.01270 (19)	0.0415 (4)
H8	0.3302	0.8725	−0.0298	0.050*
C9	0.1078 (2)	0.86943 (14)	−0.0339 (2)	0.0485 (5)
C10	0.0062 (3)	0.83549 (16)	0.0326 (3)	0.0574 (6)
H10	−0.0963	0.8480	0.0027	0.069*
C11	0.0547 (3)	0.78367 (17)	0.1417 (3)	0.0579 (6)
H11	−0.0150	0.7622	0.1858	0.069*
C12	0.2064 (2)	0.76310 (15)	0.1869 (2)	0.0470 (5)
H12	0.2388	0.7277	0.2607	0.056*
C13	0.5968 (3)	0.56894 (17)	0.3359 (2)	0.0578 (6)
H13A	0.5926	0.6284	0.3629	0.069*
H13B	0.6929	0.5578	0.3168	0.069*
H13C	0.5841	0.5312	0.4058	0.069*
C14	0.1627 (3)	0.38099 (18)	0.1097 (3)	0.0747 (8)
H14A	0.1046	0.3909	0.1738	0.090*
H14B	0.2248	0.3303	0.1341	0.090*
H14C	0.0955	0.3722	0.0243	0.090*
C15	0.0547 (3)	0.92755 (19)	−0.1527 (3)	0.0722 (8)
H15A	0.1317	0.9310	−0.2010	0.087*
H15B	0.0345	0.9847	−0.1239	0.087*
H15C	−0.0361	0.9040	−0.2087	0.087*
N1	0.46833 (19)	0.77649 (11)	0.16714 (16)	0.0385 (4)
H1N	0.499 (3)	0.7705 (15)	0.249 (2)	0.046*
O1	0.69751 (16)	0.69397 (11)	0.16345 (16)	0.0528 (4)
O2	0.51059 (18)	0.72673 (10)	−0.04494 (14)	0.0497 (4)
S1	0.54326 (5)	0.70137 (3)	0.09104 (5)	0.03742 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0366 (9)	0.0369 (10)	0.0394 (10)	0.0039 (8)	0.0121 (8)	−0.0016 (8)
C2	0.0402 (10)	0.0411 (11)	0.0437 (11)	0.0093 (8)	0.0132 (8)	0.0034 (8)
C3	0.0516 (12)	0.0411 (11)	0.0600 (13)	0.0067 (9)	0.0230 (10)	0.0058 (10)
C4	0.0462 (12)	0.0414 (11)	0.0754 (16)	−0.0002 (9)	0.0270 (11)	−0.0091 (11)
C5	0.0492 (13)	0.0552 (14)	0.0613 (14)	−0.0057 (11)	0.0049 (10)	−0.0138 (11)
C6	0.0516 (12)	0.0511 (13)	0.0411 (11)	0.0000 (10)	0.0044 (9)	−0.0020 (9)
C7	0.0386 (10)	0.0353 (10)	0.0351 (9)	−0.0017 (8)	0.0106 (7)	−0.0069 (8)
C8	0.0456 (11)	0.0397 (10)	0.0417 (10)	−0.0010 (9)	0.0154 (8)	−0.0017 (8)
C9	0.0483 (12)	0.0447 (12)	0.0512 (12)	0.0073 (9)	0.0093 (9)	−0.0012 (9)
C10	0.0404 (12)	0.0573 (14)	0.0746 (16)	0.0049 (10)	0.0141 (11)	−0.0018 (12)
C11	0.0488 (13)	0.0625 (15)	0.0695 (15)	−0.0050 (11)	0.0283 (11)	0.0010 (12)
C12	0.0501 (12)	0.0504 (12)	0.0434 (11)	−0.0025 (10)	0.0167 (9)	0.0015 (9)
C13	0.0599 (14)	0.0602 (14)	0.0476 (13)	0.0055 (12)	0.0021 (10)	0.0126 (11)
C14	0.0625 (16)	0.0534 (15)	0.116 (2)	−0.0128 (12)	0.0367 (16)	−0.0095 (15)
C15	0.0686 (17)	0.0737 (18)	0.0720 (17)	0.0219 (14)	0.0124 (13)	0.0188 (14)
N1	0.0411 (9)	0.0435 (9)	0.0297 (8)	−0.0028 (7)	0.0064 (7)	−0.0042 (7)
O1	0.0348 (8)	0.0641 (10)	0.0587 (9)	−0.0024 (7)	0.0101 (7)	0.0024 (8)
O2	0.0614 (9)	0.0565 (9)	0.0359 (7)	−0.0010 (7)	0.0207 (7)	0.0015 (7)
S1	0.0361 (3)	0.0441 (3)	0.0336 (3)	−0.0008 (2)	0.01146 (18)	0.0008 (2)

Geometric parameters (Å, º) top

C1—C6	1.386 (3)	C10—C11	1.371 (4)
C1—C2	1.403 (3)	C10—H10	0.9300
C1—S1	1.764 (2)	C11—C12	1.385 (3)
C2—C3	1.390 (3)	C11—H11	0.9300
C2—C13	1.506 (3)	C12—H12	0.9300
C3—C4	1.383 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.376 (3)	C13—H13C	0.9600
C4—C14	1.509 (3)	C14—H14A	0.9600
C5—C6	1.383 (3)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C7—C8	1.382 (3)	C15—H15B	0.9600
C7—C12	1.386 (3)	C15—H15C	0.9600
C7—N1	1.439 (2)	N1—S1	1.6402 (17)
C8—C9	1.390 (3)	N1—H1N	0.83 (2)
C8—H8	0.9300	O1—S1	1.4291 (15)
C9—C10	1.385 (3)	O2—S1	1.4298 (15)
C9—C15	1.508 (3)

C6—C1—C2	120.74 (19)	C12—C11—H11	119.7
C6—C1—S1	117.03 (16)	C11—C12—C7	119.4 (2)
C2—C1—S1	122.10 (15)	C11—C12—H12	120.3
C3—C2—C1	116.67 (19)	C7—C12—H12	120.3
C3—C2—C13	118.75 (19)	C2—C13—H13A	109.5
C1—C2—C13	124.57 (19)	C2—C13—H13B	109.5
C4—C3—C2	123.5 (2)	H13A—C13—H13B	109.5
C4—C3—H3	118.2	C2—C13—H13C	109.5
C2—C3—H3	118.2	H13A—C13—H13C	109.5
C5—C4—C3	118.1 (2)	H13B—C13—H13C	109.5
C5—C4—C14	121.0 (2)	C4—C14—H14A	109.5
C3—C4—C14	120.9 (2)	C4—C14—H14B	109.5
C4—C5—C6	120.8 (2)	H14A—C14—H14B	109.5
C4—C5—H5	119.6	C4—C14—H14C	109.5
C6—C5—H5	119.6	H14A—C14—H14C	109.5
C5—C6—C1	120.1 (2)	H14B—C14—H14C	109.5
C5—C6—H6	119.9	C9—C15—H15A	109.5
C1—C6—H6	119.9	C9—C15—H15B	109.5
C8—C7—C12	119.67 (19)	H15A—C15—H15B	109.5
C8—C7—N1	119.79 (17)	C9—C15—H15C	109.5
C12—C7—N1	120.51 (18)	H15A—C15—H15C	109.5
C7—C8—C9	121.15 (19)	H15B—C15—H15C	109.5
C7—C8—H8	119.4	C7—N1—S1	119.08 (13)
C9—C8—H8	119.4	C7—N1—H1N	115.2 (16)
C10—C9—C8	118.3 (2)	S1—N1—H1N	109.8 (16)
C10—C9—C15	120.9 (2)	O1—S1—O2	119.10 (9)
C8—C9—C15	120.8 (2)	O1—S1—N1	105.78 (9)
C11—C10—C9	120.9 (2)	O2—S1—N1	106.05 (9)
C11—C10—H10	119.5	O1—S1—C1	110.99 (9)
C9—C10—H10	119.5	O2—S1—C1	107.19 (9)
C10—C11—C12	120.6 (2)	N1—S1—C1	107.04 (9)
C10—C11—H11	119.7

C6—C1—C2—C3	−0.2 (3)	C8—C9—C10—C11	0.2 (4)
S1—C1—C2—C3	175.52 (14)	C15—C9—C10—C11	−179.0 (2)
C6—C1—C2—C13	178.9 (2)	C9—C10—C11—C12	−0.9 (4)
S1—C1—C2—C13	−5.4 (3)	C10—C11—C12—C7	0.3 (4)
C1—C2—C3—C4	−0.5 (3)	C8—C7—C12—C11	1.0 (3)
C13—C2—C3—C4	−179.7 (2)	N1—C7—C12—C11	179.05 (19)
C2—C3—C4—C5	1.2 (3)	C8—C7—N1—S1	−80.5 (2)
C2—C3—C4—C14	−178.8 (2)	C12—C7—N1—S1	101.5 (2)
C3—C4—C5—C6	−1.2 (3)	C7—N1—S1—O1	−176.76 (14)
C14—C4—C5—C6	178.8 (2)	C7—N1—S1—O2	55.85 (17)
C4—C5—C6—C1	0.5 (4)	C7—N1—S1—C1	−58.35 (17)
C2—C1—C6—C5	0.2 (3)	C6—C1—S1—O1	−148.09 (16)
S1—C1—C6—C5	−175.76 (17)	C2—C1—S1—O1	36.00 (19)
C12—C7—C8—C9	−1.7 (3)	C6—C1—S1—O2	−16.48 (19)
N1—C7—C8—C9	−179.83 (18)	C2—C1—S1—O2	167.61 (15)
C7—C8—C9—C10	1.1 (3)	C6—C1—S1—N1	96.94 (17)
C7—C8—C9—C15	−179.6 (2)	C2—C1—S1—N1	−78.97 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.83 (2)	2.13 (3)	2.932 (2)	162 (2)

Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇NO₂S
M_r	275.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	9.110 (1), 15.367 (2), 10.422 (1)
β (°)	104.05 (1)
V (Å³)	1415.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.40 × 0.40 × 0.26

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	0.915, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	5538, 2870, 2375
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.112, 1.06
No. of reflections	2870
No. of parameters	178
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.34

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···O2ⁱ	0.83 (2)	2.13 (3)	2.932 (2)	162 (2)

Symmetry code: (i) x, −y+3/2, z+1/2.

References

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Volume 66| Part 4| April 2010| Page o989

doi:10.1107/S1600536810011529

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