N-(3,4-Dichloro­phen­yl)-2,4-dimethyl­benzene­sulfonamide

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

doi:10.1107/S1600536809028840

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1976

doi:10.1107/S1600536809028840

Open

access

N-(3,4-Dichlorophenyl)-2,4-dimethylbenzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. G. Nirmala ^a 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 July 2009; accepted 21 July 2009; online 25 July 2009)

In the crystal structure of the title compound, C₁₄H₁₃Cl₂NO₂S, the configurations of the N—C bond with respect to the S=O bonds are trans and gauche. The molecule is bent at the S atom with a C—SO₂—NH—C torsion angle of −69.7 (2)°. The conformation of the N—H bond is syn to the 3-chloro group in the substituted aniline ring. The two benzene rings are tilted with respect to each other by 82.4 (1)°. The presence of N—H⋯O(S) hydrogen bonding packs the molecules into supramolecular chains along the b axis.

Related literature

For our study of the effect 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

C₁₄H₁₃Cl₂NO₂S
M_r = 330.21
Monoclinic, P 2₁ /c
a = 8.8046 (7) Å
b = 9.2688 (8) Å
c = 18.947 (1) Å
β = 99.644 (8)°
V = 1524.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.56 mm⁻¹
T = 299 K
0.44 × 0.40 × 0.38 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 = 0.790, T_max = 0.815
10274 measured reflections
3064 independent reflections
2618 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.100
S = 1.05
3064 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.833 (16)	2.176 (17)	2.984 (2)	164 (2)
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536809028840/tk2510sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028840/tk2510Isup2.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 2,4-dimethyl-N-(3,4-dichlorophenyl)benzenesulfonamide (I) has been determined. The conformations of the N—C bond in the C—SO₂—NH—C segment are trans and gauche to the S=O bonds (Fig. 1). The molecule is bent at the S atom with the C—SO₂—NH—C torsion angle of -69.7 (2)°, compared to the values of -48.2 (2)° in 2,4-dichloro-N-(3,4-dichlorophenyl)benzenesulfonamide (II) (Gowda et al., 2009b), and 46.1 (3)° and 47.7 (3)° in the two independent molecules of 2,4-dimethyl-N-(phenyl)benzenesulfonamide (III) (Gowda et al., 2009a). The conformation of the N—H bond is syn to the meta-chloro group in the substituted aniline ring. The two benzene rings in (I) are tilted by 82.4 (1)° to each other compared to the values of 68.9 (1)° in II, and 67.5 (1)° and 72.9 (1)° in III. The other bond parameters in (I) are similar to those observed in II, III, and other aryl sulfonamides (Gowda et al., 2008; Perlovich et al., 2006; Gelbrich et al., 2007). The crystal packing of molecules in (I) is via N—H···O(S) hydrogen bonding (Table 1) leading to a supramolecular chain.

Related literature top

For our study of effect 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

A solution of 1,3-xylene (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 3,4-dichloroaniline in a 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-(3,4-dichlorophenyl)benzenesulfonamide, was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The prisms used in the X-ray analysis 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

N-(3,4-Dichlorophenyl)-2,4-dimethylbenzenesulfonamide top

Crystal data top

C₁₄H₁₃Cl₂NO₂S	F(000) = 680
M_r = 330.21	D_x = 1.439 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4751 reflections
a = 8.8046 (7) Å	θ = 3.0–27.6°
b = 9.2688 (8) Å	µ = 0.56 mm⁻¹
c = 18.947 (1) Å	T = 299 K
β = 99.644 (8)°	Prism, colourless
V = 1524.4 (2) Å³	0.44 × 0.40 × 0.38 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3064 independent reflections
Radiation source: fine-focus sealed tube	2618 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→10
T_min = 0.790, T_max = 0.815	k = −11→11
10274 measured reflections	l = −23→23

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0506P)² + 0.7353P] where P = (F_o² + 2F_c²)/3
3064 reflections	(Δ/σ)_max = 0.007
186 parameters	Δρ_max = 0.27 e Å⁻³
1 restraint	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₄H₁₃Cl₂NO₂S	V = 1524.4 (2) Å³
M_r = 330.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.8046 (7) Å	µ = 0.56 mm⁻¹
b = 9.2688 (8) Å	T = 299 K
c = 18.947 (1) Å	0.44 × 0.40 × 0.38 mm
β = 99.644 (8)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3064 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2618 reflections with I > 2σ(I)
T_min = 0.790, T_max = 0.815	R_int = 0.013
10274 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.27 e Å⁻³
3064 reflections	Δρ_min = −0.39 e Å⁻³
186 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	0.7751 (2)	0.1105 (2)	0.26937 (9)	0.0342 (4)
C2	0.7595 (2)	0.0272 (2)	0.32852 (10)	0.0405 (4)
H2	0.8407	−0.0308	0.3497	0.049*
C3	0.6243 (2)	0.0301 (2)	0.35611 (10)	0.0425 (5)
C4	0.5020 (2)	0.1148 (2)	0.32506 (10)	0.0425 (5)
C5	0.5178 (2)	0.1972 (3)	0.26616 (10)	0.0472 (5)
H5	0.4360	0.2544	0.2449	0.057*
C6	0.6528 (2)	0.1963 (2)	0.23813 (10)	0.0441 (5)
H6	0.6618	0.2529	0.1985	0.053*
C7	0.8600 (2)	0.1276 (2)	0.09846 (9)	0.0334 (4)
C8	0.8733 (2)	−0.0147 (2)	0.07500 (10)	0.0363 (4)
C9	0.7833 (2)	−0.0518 (2)	0.01025 (10)	0.0410 (4)
H9	0.7907	−0.1453	−0.0067	0.049*
C10	0.6828 (2)	0.0432 (2)	−0.03070 (10)	0.0403 (4)
C11	0.6726 (2)	0.1824 (2)	−0.00542 (10)	0.0434 (5)
H11	0.6057	0.2479	−0.0317	0.052*
C12	0.7608 (2)	0.2250 (2)	0.05836 (10)	0.0406 (4)
H12	0.7537	0.3191	0.0746	0.049*
C13	0.9776 (3)	−0.1262 (2)	0.11551 (13)	0.0515 (5)
H13A	0.9396	−0.1519	0.1584	0.062*
H13B	1.0797	−0.0874	0.1277	0.062*
H13C	0.9800	−0.2103	0.0862	0.062*
C14	0.5881 (3)	−0.0036 (3)	−0.10031 (11)	0.0529 (5)
H14A	0.5855	−0.1071	−0.1026	0.064*
H14B	0.6331	0.0336	−0.1394	0.064*
H14C	0.4851	0.0328	−0.1035	0.064*
N1	0.91696 (19)	0.1015 (2)	0.24438 (8)	0.0407 (4)
H1N	0.976 (2)	0.035 (2)	0.2605 (12)	0.049*
O1	0.92732 (17)	0.33947 (15)	0.18616 (7)	0.0471 (4)
O2	1.12802 (16)	0.15602 (19)	0.18124 (8)	0.0530 (4)
Cl1	0.61158 (9)	−0.07351 (7)	0.43079 (4)	0.0753 (2)
Cl2	0.33330 (7)	0.12189 (9)	0.36022 (3)	0.0680 (2)
S1	0.96962 (5)	0.19135 (5)	0.17881 (2)	0.03717 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0378 (10)	0.0348 (9)	0.0301 (8)	−0.0019 (7)	0.0057 (7)	−0.0059 (7)
C2	0.0482 (11)	0.0329 (10)	0.0418 (10)	0.0070 (8)	0.0121 (8)	0.0008 (8)
C3	0.0561 (12)	0.0323 (10)	0.0428 (10)	−0.0013 (9)	0.0190 (9)	−0.0015 (8)
C4	0.0378 (10)	0.0490 (12)	0.0424 (10)	−0.0053 (9)	0.0116 (8)	−0.0117 (9)
C5	0.0372 (11)	0.0635 (14)	0.0389 (10)	0.0079 (9)	0.0010 (8)	−0.0018 (9)
C6	0.0414 (11)	0.0577 (13)	0.0325 (9)	0.0056 (9)	0.0045 (8)	0.0039 (9)
C7	0.0347 (9)	0.0356 (10)	0.0313 (8)	−0.0044 (7)	0.0093 (7)	0.0007 (7)
C8	0.0373 (9)	0.0337 (9)	0.0398 (9)	−0.0012 (8)	0.0121 (7)	0.0019 (7)
C9	0.0476 (11)	0.0346 (10)	0.0421 (10)	−0.0028 (8)	0.0112 (8)	−0.0050 (8)
C10	0.0438 (11)	0.0453 (11)	0.0330 (9)	−0.0057 (9)	0.0100 (8)	−0.0020 (8)
C11	0.0520 (12)	0.0418 (11)	0.0353 (9)	0.0052 (9)	0.0037 (8)	0.0059 (8)
C12	0.0517 (11)	0.0336 (10)	0.0370 (9)	0.0028 (8)	0.0087 (8)	0.0008 (8)
C13	0.0532 (13)	0.0401 (11)	0.0588 (13)	0.0051 (10)	0.0027 (10)	0.0035 (10)
C14	0.0577 (13)	0.0602 (14)	0.0391 (11)	−0.0061 (11)	0.0032 (9)	−0.0050 (10)
N1	0.0381 (9)	0.0497 (10)	0.0350 (8)	0.0079 (7)	0.0080 (7)	0.0061 (7)
O1	0.0542 (9)	0.0374 (8)	0.0481 (8)	−0.0112 (6)	0.0038 (6)	−0.0065 (6)
O2	0.0326 (7)	0.0724 (11)	0.0544 (9)	−0.0062 (7)	0.0087 (6)	−0.0024 (7)
Cl1	0.0973 (5)	0.0599 (4)	0.0818 (5)	0.0169 (3)	0.0531 (4)	0.0292 (3)
Cl2	0.0443 (3)	0.0965 (5)	0.0679 (4)	−0.0024 (3)	0.0234 (3)	−0.0037 (3)
S1	0.0339 (2)	0.0413 (3)	0.0365 (2)	−0.00631 (19)	0.00630 (18)	−0.00184 (19)

Geometric parameters (Å, º) top

C1—C2	1.387 (3)	C9—C10	1.389 (3)
C1—C6	1.389 (3)	C9—H9	0.9300
C1—N1	1.410 (2)	C10—C11	1.385 (3)
C2—C3	1.379 (3)	C10—C14	1.501 (3)
C2—H2	0.9300	C11—C12	1.380 (3)
C3—C4	1.382 (3)	C11—H11	0.9300
C3—Cl1	1.729 (2)	C12—H12	0.9300
C4—C5	1.378 (3)	C13—H13A	0.9600
C4—Cl2	1.7283 (19)	C13—H13B	0.9600
C5—C6	1.381 (3)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C12	1.391 (3)	C14—H14C	0.9600
C7—C8	1.403 (3)	N1—S1	1.6264 (17)
C7—S1	1.7623 (18)	N1—H1N	0.833 (16)
C8—C9	1.387 (3)	O1—S1	1.4353 (15)
C8—C13	1.505 (3)	O2—S1	1.4258 (15)

C2—C1—C6	119.25 (18)	C9—C10—C14	121.03 (19)
C2—C1—N1	116.83 (17)	C12—C11—C10	120.66 (18)
C6—C1—N1	123.92 (17)	C12—C11—H11	119.7
C3—C2—C1	120.29 (18)	C10—C11—H11	119.7
C3—C2—H2	119.9	C11—C12—C7	120.17 (18)
C1—C2—H2	119.9	C11—C12—H12	119.9
C2—C3—C4	120.68 (18)	C7—C12—H12	119.9
C2—C3—Cl1	118.55 (16)	C8—C13—H13A	109.5
C4—C3—Cl1	120.77 (15)	C8—C13—H13B	109.5
C5—C4—C3	118.87 (18)	H13A—C13—H13B	109.5
C5—C4—Cl2	120.05 (16)	C8—C13—H13C	109.5
C3—C4—Cl2	121.06 (16)	H13A—C13—H13C	109.5
C4—C5—C6	121.20 (19)	H13B—C13—H13C	109.5
C4—C5—H5	119.4	C10—C14—H14A	109.5
C6—C5—H5	119.4	C10—C14—H14B	109.5
C5—C6—C1	119.71 (18)	H14A—C14—H14B	109.5
C5—C6—H6	120.1	C10—C14—H14C	109.5
C1—C6—H6	120.1	H14A—C14—H14C	109.5
C12—C7—C8	121.01 (17)	H14B—C14—H14C	109.5
C12—C7—S1	117.22 (14)	C1—N1—S1	127.44 (14)
C8—C7—S1	121.76 (14)	C1—N1—H1N	117.1 (16)
C9—C8—C7	116.59 (17)	S1—N1—H1N	114.8 (16)
C9—C8—C13	119.36 (18)	O2—S1—O1	119.00 (9)
C7—C8—C13	124.05 (18)	O2—S1—N1	105.08 (9)
C8—C9—C10	123.55 (18)	O1—S1—N1	107.69 (9)
C8—C9—H9	118.2	O2—S1—C7	109.99 (9)
C10—C9—H9	118.2	O1—S1—C7	106.92 (9)
C11—C10—C9	118.01 (18)	N1—S1—C7	107.66 (9)
C11—C10—C14	120.96 (19)

C6—C1—C2—C3	−0.2 (3)	C8—C9—C10—C11	0.2 (3)
N1—C1—C2—C3	−179.96 (17)	C8—C9—C10—C14	−179.83 (18)
C1—C2—C3—C4	0.5 (3)	C9—C10—C11—C12	0.4 (3)
C1—C2—C3—Cl1	−179.00 (14)	C14—C10—C11—C12	−179.54 (19)
C2—C3—C4—C5	−0.3 (3)	C10—C11—C12—C7	−0.7 (3)
Cl1—C3—C4—C5	179.16 (16)	C8—C7—C12—C11	0.3 (3)
C2—C3—C4—Cl2	−178.74 (15)	S1—C7—C12—C11	179.45 (15)
Cl1—C3—C4—Cl2	0.7 (2)	C2—C1—N1—S1	−177.17 (15)
C3—C4—C5—C6	−0.1 (3)	C6—C1—N1—S1	3.1 (3)
Cl2—C4—C5—C6	178.33 (16)	C1—N1—S1—O2	173.04 (16)
C4—C5—C6—C1	0.4 (3)	C1—N1—S1—O1	45.23 (19)
C2—C1—C6—C5	−0.2 (3)	C1—N1—S1—C7	−69.74 (18)
N1—C1—C6—C5	179.52 (18)	C12—C7—S1—O2	−129.57 (15)
C12—C7—C8—C9	0.3 (3)	C8—C7—S1—O2	49.56 (17)
S1—C7—C8—C9	−178.82 (13)	C12—C7—S1—O1	0.97 (17)
C12—C7—C8—C13	−179.77 (19)	C8—C7—S1—O1	−179.90 (14)
S1—C7—C8—C13	1.1 (3)	C12—C7—S1—N1	116.45 (15)
C7—C8—C9—C10	−0.6 (3)	C8—C7—S1—N1	−64.42 (16)
C13—C8—C9—C10	179.49 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.83 (2)	2.18 (2)	2.984 (2)	164 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃Cl₂NO₂S
M_r	330.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	8.8046 (7), 9.2688 (8), 18.947 (1)
β (°)	99.644 (8)
V (Å³)	1524.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.56
Crystal size (mm)	0.44 × 0.40 × 0.38

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	0.790, 0.815
No. of measured, independent and observed [I > 2σ(I)] reflections	10274, 3064, 2618
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.100, 1.05
No. of reflections	3064
No. of parameters	186
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.39

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	0.833 (16)	2.176 (17)	2.984 (2)	164 (2)

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

Acknowledgements

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

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, o1825. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009a). Acta Cryst. E65, o576. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2009b). Acta Cryst. E65, o1940. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Perlovich, 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar