4-Chloro-N-(3,5-dimethyl­phen­yl)benzamide

Rodrigues, V.Z.; Gowda, B.T.; Vrábel, V.; Kožíšek, J.

doi:10.1107/S1600536812007180

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o820

doi:10.1107/S1600536812007180

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4-Chloro-N-(3,5-dimethylphenyl)benzamide

Vinola Z. Rodrigues,^a B. Thimme Gowda,^a ^* Viktor Vrábel ^b and Jozef Kožíšek ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 15 February 2012; accepted 17 February 2012; online 24 February 2012)

In the molecular structure of the title compound, C₁₅H₁₄ClNO, the amide group forms dihedral angles of 15.8 (2) and 27.2 (2)°, respectively, with the benzoyl and aniline rings, while the angle between the benzoyl and aniline rings is 11.5 (1)°. The crystal structure is stabilized by N—H⋯O hydrogen bonds, which give rise to infinite chains running along the c axis.

Related literature

For studies, including ours, on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003 ); Gowda et al. (2000 ); Rodrigues et al. (2011 ); Saeed et al. (2010 ); N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ); N-chloroarylamides, see: Gowda et al. (2003 ); Jyothi & Gowda (2004 ); N-bromoarylsulfonamides, see: Usha & Gowda (2006 ).

Experimental

Crystal data

C₁₅H₁₄ClNO
M_r = 259.72
Monoclinic, P 2₁ /c
a = 14.2763 (7) Å
b = 10.7038 (6) Å
c = 9.5245 (4) Å
β = 108.087 (5)°
V = 1383.52 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 295 K
0.35 × 0.25 × 0.15 mm

Data collection

Oxford Xcalibur CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.916, T_max = 0.958
22077 measured reflections
2433 independent reflections
1542 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.152
S = 1.03
2433 reflections
169 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86 (1)	2.12 (1)	2.948 (2)	163 (2)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812007180/rk2336sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007180/rk2336Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007180/rk2336Isup3.cml

checkCIF report

Comment top

The amide and sulfonamide moieties are the constituents of many biologically important compounds. As part of studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 2000; Rodrigues et al., 2011; Saeed et al., 2010), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-chloroarylsulfonamides (Gowda et al., 2003; Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of 4-chloro-N-(3,5-dimethylphenyl)benzamide has been determined (Fig. 1).

In the title compound, one of the m-methyl groups in the aniline ring is positioned syn to the N—H bond, while the other m-methyl group is positioned anti to the N—H bond, the latter and the C═O bond being anti to each other, similar to that observed in 4-chloro-N-(3-methylphenyl)benzamide (Rodrigues et al., 2011).

In the title compound, the amide group forms dihedral angles of 15.8 (2)° and 27.2 (2)°, respectively, with the benzoyl and aniline rings, while the angle between the benzoyl and aniline rings is 11.5 (1)°.

In the crystal structure, classical intermolecular N1—H1···O1ⁱ hydrogen bonds (Table 1) link the molecules into infinite chains running along the c-axis. Symmetry code: (i) x, -y + 1/2, z - 1/2. Part of the crystal structure is shown in Fig. 2.

Related literature top

For studies, including ours, on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (2000); Rodrigues et al. (2011); Saeed et al. (2010); N-(aryl)-methanesulfonamides, see: Gowda et al. (2007); N-chloroarylamides, see: Gowda et al. (2003); Jyothi & Gowda (2004); N-bromoarylsulfonamides, see: Usha & Gowda (2006).

Experimental top

The title compound was prepared by a method similar to the one described by Rodrigues et al. (2011). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra.

Plate like colourless single crystals of the title compound used in the X-ray diffraction studies were obtained by slow evaporation of the solvent from its ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (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: DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radius.
	Fig. 2. Packing view of the title compound. Molecular chains along c-axis are generated by classical intermolecular N—H···O hydrogen bonds which are shown as dashed lines. Other H atoms have been omitted for clarity.

4-Chloro-N-(3,5-dimethylphenyl)benzamide top

Crystal data top

C₁₅H₁₄ClNO	F(000) = 544
M_r = 259.72	D_x = 1.247 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.2763 (7) Å	Cell parameters from 2433 reflections
b = 10.7038 (6) Å	θ = 0.9–1.0°
c = 9.5245 (4) Å	µ = 0.26 mm⁻¹
β = 108.087 (5)°	T = 295 K
V = 1383.52 (12) Å³	Plate, colourless
Z = 4	0.35 × 0.25 × 0.15 mm

Data collection top

Oxford Xcalibur CCD diffractometer	2433 independent reflections
Radiation source: fine-focus sealed tube	1542 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 10.4340 pixels mm^-1	θ_max = 25.0°, θ_min = 3.6°
ω scans with κ offsets	h = −16→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −12→12
T_min = 0.916, T_max = 0.958	l = −11→11
22077 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0866P)² + 0.1343P] where P = (F_o² + 2F_c²)/3
2433 reflections	(Δ/σ)_max < 0.001
169 parameters	Δρ_max = 0.34 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₅H₁₄ClNO	V = 1383.52 (12) Å³
M_r = 259.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.2763 (7) Å	µ = 0.26 mm⁻¹
b = 10.7038 (6) Å	T = 295 K
c = 9.5245 (4) Å	0.35 × 0.25 × 0.15 mm
β = 108.087 (5)°

Data collection top

Oxford Xcalibur CCD diffractometer	2433 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1542 reflections with I > 2σ(I)
T_min = 0.916, T_max = 0.958	R_int = 0.036
22077 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.34 e Å⁻³
2433 reflections	Δρ_min = −0.19 e Å⁻³
169 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.45950 (16)	0.1593 (2)	0.5588 (2)	0.0589 (6)
C2	0.41450 (19)	0.2143 (3)	0.4238 (3)	0.0841 (8)
H2	0.4474	0.2769	0.3902	0.101*
C3	0.3222 (2)	0.1787 (3)	0.3381 (3)	0.0940 (9)
H3	0.2935	0.2156	0.2465	0.113*
C4	0.27271 (18)	0.0882 (3)	0.3885 (3)	0.0733 (7)
C5	0.3153 (2)	0.0321 (2)	0.5211 (3)	0.0769 (7)
H5	0.2816	−0.0294	0.5549	0.092*
C6	0.40845 (18)	0.0672 (2)	0.6046 (3)	0.0717 (7)
H6	0.4378	0.0276	0.6945	0.086*
C7	0.55792 (16)	0.1969 (2)	0.6601 (2)	0.0601 (6)
C8	0.70886 (16)	0.3186 (2)	0.6783 (2)	0.0582 (6)
C9	0.73635 (18)	0.4271 (2)	0.6217 (2)	0.0664 (6)
H9	0.6927	0.4638	0.5384	0.080*
C10	0.82705 (19)	0.4817 (2)	0.6865 (3)	0.0702 (7)
C11	0.89035 (18)	0.4265 (2)	0.8120 (3)	0.0701 (7)
H11	0.9513	0.4632	0.8576	0.084*
C12	0.86517 (17)	0.3179 (2)	0.8711 (2)	0.0643 (6)
C13	0.77377 (16)	0.2640 (2)	0.8028 (2)	0.0615 (6)
H13	0.7560	0.1908	0.8408	0.074*
C14	0.93520 (19)	0.2590 (3)	1.0067 (3)	0.0848 (8)
H14A	0.9362	0.1702	0.9931	0.127*
H14B	0.9139	0.2771	1.0907	0.127*
H14C	1.0002	0.2922	1.0227	0.127*
C15	0.8581 (2)	0.5971 (3)	0.6211 (3)	0.1037 (10)
H15A	0.8784	0.6606	0.6957	0.156*
H15B	0.8037	0.6273	0.5411	0.156*
H15C	0.9120	0.5768	0.5850	0.156*
N1	0.61598 (14)	0.26628 (19)	0.60271 (18)	0.0631 (5)
H1	0.5938 (16)	0.283 (2)	0.5099 (6)	0.070 (7)*
O1	0.58311 (11)	0.16623 (18)	0.79101 (16)	0.0777 (6)
Cl1	0.15289 (5)	0.04825 (8)	0.28458 (9)	0.1054 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0569 (13)	0.0741 (15)	0.0468 (11)	0.0012 (12)	0.0178 (10)	−0.0037 (11)
C2	0.0613 (15)	0.119 (2)	0.0659 (15)	−0.0208 (15)	0.0113 (12)	0.0201 (15)
C3	0.0700 (17)	0.133 (3)	0.0692 (16)	−0.0179 (17)	0.0069 (14)	0.0241 (16)
C4	0.0609 (15)	0.0874 (18)	0.0697 (15)	−0.0113 (13)	0.0174 (13)	−0.0095 (14)
C5	0.0791 (18)	0.0753 (17)	0.0766 (17)	−0.0167 (14)	0.0247 (14)	0.0008 (14)
C6	0.0728 (16)	0.0820 (18)	0.0591 (14)	−0.0083 (13)	0.0185 (13)	0.0053 (12)
C7	0.0569 (13)	0.0793 (16)	0.0463 (12)	0.0042 (12)	0.0192 (11)	−0.0057 (11)
C8	0.0559 (13)	0.0741 (16)	0.0442 (11)	0.0000 (11)	0.0149 (10)	−0.0091 (11)
C9	0.0721 (16)	0.0753 (16)	0.0491 (12)	−0.0010 (13)	0.0148 (11)	−0.0028 (11)
C10	0.0768 (16)	0.0743 (17)	0.0604 (14)	−0.0110 (13)	0.0227 (13)	−0.0076 (12)
C11	0.0584 (14)	0.0906 (19)	0.0608 (14)	−0.0109 (13)	0.0177 (12)	−0.0154 (13)
C12	0.0556 (13)	0.0816 (17)	0.0549 (13)	0.0019 (12)	0.0161 (11)	−0.0087 (12)
C13	0.0586 (14)	0.0726 (15)	0.0534 (12)	−0.0011 (11)	0.0176 (11)	−0.0034 (11)
C14	0.0606 (16)	0.107 (2)	0.0763 (16)	0.0048 (14)	0.0062 (13)	0.0045 (15)
C15	0.115 (2)	0.098 (2)	0.095 (2)	−0.0299 (19)	0.0264 (18)	0.0059 (17)
N1	0.0596 (11)	0.0856 (14)	0.0414 (10)	−0.0081 (10)	0.0116 (9)	−0.0012 (10)
O1	0.0674 (10)	0.1213 (15)	0.0447 (9)	−0.0051 (9)	0.0177 (8)	0.0041 (9)
Cl1	0.0723 (5)	0.1250 (8)	0.1045 (6)	−0.0281 (4)	0.0065 (4)	−0.0081 (4)

Geometric parameters (Å, º) top

C1—C6	1.375 (3)	C9—C10	1.379 (3)
C1—C2	1.378 (3)	C9—H9	0.9300
C1—C7	1.492 (3)	C10—C11	1.387 (4)
C2—C3	1.371 (4)	C10—C15	1.511 (4)
C2—H2	0.9300	C11—C12	1.387 (3)
C3—C4	1.370 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.390 (3)
C4—C5	1.359 (4)	C12—C14	1.504 (3)
C4—Cl1	1.743 (2)	C13—H13	0.9300
C5—C6	1.373 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—O1	1.230 (2)	C15—H15A	0.9600
C7—N1	1.349 (3)	C15—H15B	0.9600
C8—C9	1.387 (3)	C15—H15C	0.9600
C8—C13	1.387 (3)	N1—H1	0.859 (2)
C8—N1	1.414 (3)

C6—C1—C2	117.6 (2)	C9—C10—C11	118.3 (2)
C6—C1—C7	118.2 (2)	C9—C10—C15	121.1 (2)
C2—C1—C7	124.1 (2)	C11—C10—C15	120.5 (2)
C3—C2—C1	121.3 (2)	C12—C11—C10	121.7 (2)
C3—C2—H2	119.3	C12—C11—H11	119.1
C1—C2—H2	119.3	C10—C11—H11	119.1
C4—C3—C2	119.6 (3)	C11—C12—C13	118.8 (2)
C4—C3—H3	120.2	C11—C12—C14	120.9 (2)
C2—C3—H3	120.2	C13—C12—C14	120.4 (2)
C5—C4—C3	120.4 (2)	C8—C13—C12	120.4 (2)
C5—C4—Cl1	119.7 (2)	C8—C13—H13	119.8
C3—C4—Cl1	119.8 (2)	C12—C13—H13	119.8
C4—C5—C6	119.4 (2)	C12—C14—H14A	109.5
C4—C5—H5	120.3	C12—C14—H14B	109.5
C6—C5—H5	120.3	H14A—C14—H14B	109.5
C5—C6—C1	121.7 (2)	C12—C14—H14C	109.5
C5—C6—H6	119.2	H14A—C14—H14C	109.5
C1—C6—H6	119.2	H14B—C14—H14C	109.5
O1—C7—N1	122.3 (2)	C10—C15—H15A	109.5
O1—C7—C1	120.3 (2)	C10—C15—H15B	109.5
N1—C7—C1	117.38 (18)	H15A—C15—H15B	109.5
C9—C8—C13	119.4 (2)	C10—C15—H15C	109.5
C9—C8—N1	117.9 (2)	H15A—C15—H15C	109.5
C13—C8—N1	122.7 (2)	H15B—C15—H15C	109.5
C10—C9—C8	121.4 (2)	C7—N1—C8	127.51 (17)
C10—C9—H9	119.3	C7—N1—H1	117.0 (16)
C8—C9—H9	119.3	C8—N1—H1	115.5 (16)

C6—C1—C2—C3	0.0 (4)	N1—C8—C9—C10	−177.95 (19)
C7—C1—C2—C3	−177.5 (2)	C8—C9—C10—C11	−1.0 (3)
C1—C2—C3—C4	1.3 (5)	C8—C9—C10—C15	177.7 (2)
C2—C3—C4—C5	−1.3 (5)	C9—C10—C11—C12	1.1 (4)
C2—C3—C4—Cl1	176.6 (2)	C15—C10—C11—C12	−177.5 (2)
C3—C4—C5—C6	0.1 (4)	C10—C11—C12—C13	−0.4 (3)
Cl1—C4—C5—C6	−177.79 (19)	C10—C11—C12—C14	179.6 (2)
C4—C5—C6—C1	1.1 (4)	C9—C8—C13—C12	0.6 (3)
C2—C1—C6—C5	−1.2 (4)	N1—C8—C13—C12	178.56 (18)
C7—C1—C6—C5	176.5 (2)	C11—C12—C13—C8	−0.4 (3)
C6—C1—C7—O1	−15.0 (3)	C14—C12—C13—C8	179.6 (2)
C2—C1—C7—O1	162.4 (2)	O1—C7—N1—C8	−3.0 (4)
C6—C1—C7—N1	165.9 (2)	C1—C7—N1—C8	176.0 (2)
C2—C1—C7—N1	−16.6 (3)	C9—C8—N1—C7	−151.7 (2)
C13—C8—C9—C10	0.2 (3)	C13—C8—N1—C7	30.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86 (1)	2.12 (1)	2.948 (2)	163 (2)

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄ClNO
M_r	259.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	14.2763 (7), 10.7038 (6), 9.5245 (4)
β (°)	108.087 (5)
V (Å³)	1383.52 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.35 × 0.25 × 0.15

Data collection
Diffractometer	Oxford Xcalibur CCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.916, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	22077, 2433, 1542
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.152, 1.03
No. of reflections	2433
No. of parameters	169
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)	0.34, −0.19

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.859 (2)	2.115 (7)	2.948 (2)	163 (2)

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS research fellowship. VV and JK thank the Slovak Grant Agencies for their financial support (VEGA Grant Agency of the Slovak Ministry of Education, grant No. 1/0679/11, and the Research and Development Agency of Slovakia, grant No. APVV-0202-10), and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

References

Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1–o3. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gowda, B. T., D'Souza, J. D. & Kumar, B. H. A. (2003). Z. Naturforsch. Teil A, 58, 51–56. CAS Google Scholar
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2570. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Paulus, H. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 711–720. CAS Google Scholar
Jyothi, K. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 64–68. CAS Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Rodrigues, V. Z., Fronc, M., Gowda, B. T. & Kožíšek, J. (2011). Acta Cryst. E67, o2903. Web of Science CSD CrossRef IUCr Journals Google Scholar
Saeed, A., Arshad, M. & Simpson, J. (2010). Acta Cryst. E66, o2808–o2809. 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
Usha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351–359. Web of Science CrossRef CAS Google Scholar