3-Chloro-N-(3-methyl­phen­yl)benzamide

Rodrigues, V.Z.; Kucková,, L.; Gowda, B.T.; Kožíšek, J.

doi:10.1107/S1600536811047271

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3277

https://doi.org/10.1107/S1600536811047271

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3-Chloro-N-(3-methylphenyl)benzamide

Vinola Z. Rodrigues,^a Lenka Kucková,,^b B. Thimme Gowda ^a ^* 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 7 November 2011; accepted 8 November 2011; online 12 November 2011)

In the molecular structure of the title compound, C₁₄H₁₂ClNO, the meta-Cl atom in the benzoyl ring is positioned syn to the C=O bond, while the meta-methyl group in the aniline ring is positioned anti to the N—H bond. The two aromatic rings make a dihedral angle of 77.4 (1)°. In the crystal, the molecules are linked by N—H⋯O hydrogen bonds, forming C(4) chains propagating in [010].

Related literature

For preparation of the title compound, see: Gowda et al. (2003 ). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000 ); Bowes et al. (2003 ); Gowda et al. (2008 ); Saeed et al. (2010 ), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ), on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005 ) and on N-chloro-amides, see: Gowda & Weiss (1994 ).

Experimental

Crystal data

C₁₄H₁₂ClNO
M_r = 245.70
Orthorhombic, P b c n
a = 9.4032 (3) Å
b = 10.0963 (2) Å
c = 25.9904 (7) Å
V = 2467.46 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 298 K
0.38 × 0.24 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ), based on expressions derived by Clark & Reid (1995 )] T_min = 0.921, T_max = 0.988
39014 measured reflections
3440 independent reflections
1666 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.191
S = 1.02
3440 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.86	2.10	2.938 (3)	163
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811047271/bt5712sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047271/bt5712Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811047271/bt5712Isup3.cml

checkCIF report

Comment top

The amide and sulfonamide moieties are the constituents of many biologically important compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bhat & Gowda, 2000; Bowes et al., 2003; Gowda et al., 2008; Saeed et al., 2010), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloro-arylamides (Gowda & Weiss, 1994), in the present work, the crystal structure of 3-Chloro-N-(3-methylphenyl)benzamide (I) has been determined (Fig.1).

In (I), the meta-Cl atom in the benzoyl ring is positioned syn to the C=O bond, while the meta-methyl group in the anilino ring is positioned anti to the N—H bond, the N—H and C=O bonds in the C—NH—C(O)—C segment being anti to each other. Further, the two aromatic rings make the dihedral angle of 77.4 (1)°, compared to the values of 9.1 (2)° and 7.3 (3)° in the two independent molecules of 3-chloro-N-(3-chlorophenyl)benzamide (Gowda et al., 2008).

In the crystal structure, intermolecular N—H···O hydrogen bonds link the molecules into infinite chains running along the b-axis. Part of the crystal structure is shown in Fig. 2.

Related literature top

For preparation of the title compound, see: Gowda et al. (2003). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000); Bowes et al. (2003); Gowda et al. (2008); Saeed et al. (2010), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007), on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005) and on N-chloro-amides, see: Gowda & Weiss (1994).

Experimental top

The title compound was prepared according to the method described by Gowda et al. (2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra.

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

Structure description top

In the crystal structure, intermolecular N—H···O hydrogen bonds link the molecules into infinite chains running along the b-axis. Part of the crystal structure is shown in Fig. 2.

For preparation of the title compound, see: Gowda et al. (2003). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000); Bowes et al. (2003); Gowda et al. (2008); Saeed et al. (2010), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007), on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005) and on N-chloro-amides, see: Gowda & Weiss (1994).

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: enCIFer (Allen et al., 2004).

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 radii.
	Fig. 2. Part of the crystal structure of the title compound. Molecular chains are generated by N—H···O hydrogen bonds which are shown by dashed lines.

3-Chloro-N-(3-methylphenyl)benzamide top

Crystal data top

C₁₄H₁₂ClNO	F(000) = 1024
M_r = 245.70	D_x = 1.323 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 6149 reflections
a = 9.4032 (3) Å	θ = 2.2–29.5°
b = 10.0963 (2) Å	µ = 0.29 mm⁻¹
c = 25.9904 (7) Å	T = 298 K
V = 2467.46 (11) Å³	Plate, colourless
Z = 8	0.38 × 0.24 × 0.04 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3440 independent reflections
Radiation source: fine-focus sealed tube	1666 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
Detector resolution: 10.4340 pixels mm^-1	θ_max = 29.5°, θ_min = 2.7°
ω scans	h = −13→13
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −14→14
T_min = 0.921, T_max = 0.988	l = −36→36
39014 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.191	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0806P)² + 0.6744P] where P = (F_o² + 2F_c²)/3
3440 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₂ClNO	V = 2467.46 (11) Å³
M_r = 245.70	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 9.4032 (3) Å	µ = 0.29 mm⁻¹
b = 10.0963 (2) Å	T = 298 K
c = 25.9904 (7) Å	0.38 × 0.24 × 0.04 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3440 independent reflections
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	1666 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.988	R_int = 0.072
39014 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.191	H-atom parameters constrained
S = 1.02	Δρ_max = 0.20 e Å⁻³
3440 reflections	Δρ_min = −0.24 e Å⁻³
154 parameters

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived (Clark & Reid, 1995).

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	0.2146 (3)	0.4686 (2)	0.23782 (10)	0.0575 (6)
C2	0.1595 (3)	0.5148 (2)	0.18676 (10)	0.0559 (6)
C3	0.1825 (3)	0.4345 (3)	0.14430 (10)	0.0615 (7)
H3A	0.2272	0.3530	0.1483	0.074*
C4	0.1393 (3)	0.4751 (3)	0.09637 (10)	0.0657 (7)
C5	0.0675 (3)	0.5920 (3)	0.08959 (11)	0.0743 (8)
H5A	0.0374	0.6179	0.0570	0.089*
C6	0.0407 (3)	0.6699 (3)	0.13170 (13)	0.0764 (8)
H6A	−0.0099	0.7484	0.1277	0.092*
C7	0.0881 (3)	0.6333 (2)	0.18017 (11)	0.0657 (7)
H7A	0.0718	0.6884	0.2082	0.079*
C8	0.3209 (3)	0.5467 (2)	0.31904 (10)	0.0546 (6)
C9	0.2617 (3)	0.4605 (2)	0.35419 (10)	0.0588 (6)
H9A	0.1822	0.4109	0.3451	0.071*
C10	0.3201 (3)	0.4473 (2)	0.40297 (10)	0.0601 (7)
C11	0.4389 (3)	0.5208 (3)	0.41499 (11)	0.0719 (8)
H11A	0.4797	0.5128	0.4474	0.086*
C12	0.4979 (3)	0.6061 (3)	0.37956 (13)	0.0770 (8)
H12A	0.5782	0.6550	0.3883	0.092*
C13	0.4390 (3)	0.6196 (3)	0.33154 (11)	0.0665 (7)
H13A	0.4788	0.6775	0.3077	0.080*
C14	0.2552 (4)	0.3530 (3)	0.44195 (12)	0.0796 (9)
H14C	0.3088	0.3565	0.4734	0.095*
H14B	0.2572	0.2644	0.4285	0.095*
H14A	0.1586	0.3784	0.4486	0.095*
N1	0.2606 (2)	0.56520 (19)	0.26937 (8)	0.0600 (6)
H1N	0.2529	0.6453	0.2585	0.072*
O1	0.2191 (2)	0.35053 (16)	0.24849 (7)	0.0776 (6)
Cl1	0.17750 (10)	0.37730 (9)	0.04296 (3)	0.0932 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0787 (16)	0.0375 (13)	0.0563 (15)	0.0021 (11)	0.0064 (13)	0.0007 (10)
C2	0.0672 (15)	0.0420 (12)	0.0585 (15)	−0.0051 (12)	0.0003 (12)	0.0033 (11)
C3	0.0768 (17)	0.0486 (14)	0.0591 (16)	0.0002 (12)	−0.0029 (13)	0.0033 (12)
C4	0.0783 (17)	0.0599 (16)	0.0590 (17)	−0.0098 (14)	−0.0038 (13)	0.0027 (12)
C5	0.087 (2)	0.0708 (18)	0.0650 (18)	−0.0045 (16)	−0.0159 (15)	0.0150 (15)
C6	0.0796 (19)	0.0596 (16)	0.090 (2)	0.0089 (14)	−0.0155 (17)	0.0102 (16)
C7	0.0780 (18)	0.0488 (14)	0.0702 (18)	−0.0001 (13)	−0.0028 (14)	0.0026 (12)
C8	0.0717 (16)	0.0376 (12)	0.0546 (15)	0.0096 (11)	0.0009 (12)	0.0013 (10)
C9	0.0708 (16)	0.0442 (13)	0.0615 (16)	0.0051 (12)	0.0008 (13)	0.0018 (11)
C10	0.0785 (18)	0.0481 (14)	0.0538 (15)	0.0142 (13)	0.0031 (13)	−0.0001 (11)
C11	0.0861 (19)	0.0670 (17)	0.0626 (17)	0.0130 (16)	−0.0118 (15)	−0.0082 (14)
C12	0.085 (2)	0.0655 (18)	0.081 (2)	−0.0042 (15)	−0.0085 (16)	−0.0060 (16)
C13	0.0766 (18)	0.0520 (15)	0.0708 (18)	−0.0030 (13)	0.0031 (15)	−0.0007 (13)
C14	0.100 (2)	0.0742 (19)	0.0640 (18)	0.0066 (16)	0.0039 (17)	0.0155 (15)
N1	0.0853 (15)	0.0348 (10)	0.0599 (13)	0.0008 (10)	−0.0027 (11)	0.0053 (9)
O1	0.1386 (18)	0.0328 (9)	0.0615 (12)	0.0018 (10)	−0.0036 (11)	0.0041 (8)
Cl1	0.1290 (8)	0.0918 (7)	0.0588 (5)	−0.0005 (5)	−0.0013 (4)	−0.0071 (4)

Geometric parameters (Å, º) top

C1—O1	1.225 (3)	C8—C9	1.379 (3)
C1—N1	1.345 (3)	C8—N1	1.422 (3)
C1—C2	1.499 (4)	C9—C10	1.388 (4)
C2—C7	1.383 (3)	C9—H9A	0.9300
C2—C3	1.386 (4)	C10—C11	1.377 (4)
C3—C4	1.373 (4)	C10—C14	1.518 (4)
C3—H3A	0.9300	C11—C12	1.377 (4)
C4—C5	1.371 (4)	C11—H11A	0.9300
C4—Cl1	1.741 (3)	C12—C13	1.372 (4)
C5—C6	1.371 (4)	C12—H12A	0.9300
C5—H5A	0.9300	C13—H13A	0.9300
C6—C7	1.386 (4)	C14—H14C	0.9600
C6—H6A	0.9300	C14—H14B	0.9600
C7—H7A	0.9300	C14—H14A	0.9600
C8—C13	1.371 (4)	N1—H1N	0.8600

O1—C1—N1	123.8 (2)	C8—C9—C10	120.4 (3)
O1—C1—C2	121.0 (2)	C8—C9—H9A	119.8
N1—C1—C2	115.2 (2)	C10—C9—H9A	119.8
C7—C2—C3	118.9 (2)	C11—C10—C9	118.4 (3)
C7—C2—C1	123.1 (2)	C11—C10—C14	120.8 (3)
C3—C2—C1	118.0 (2)	C9—C10—C14	120.7 (3)
C4—C3—C2	120.2 (2)	C10—C11—C12	120.8 (3)
C4—C3—H3A	119.9	C10—C11—H11A	119.6
C2—C3—H3A	119.9	C12—C11—H11A	119.6
C5—C4—C3	121.3 (3)	C13—C12—C11	120.5 (3)
C5—C4—Cl1	119.2 (2)	C13—C12—H12A	119.8
C3—C4—Cl1	119.6 (2)	C11—C12—H12A	119.8
C4—C5—C6	118.8 (3)	C8—C13—C12	119.3 (3)
C4—C5—H5A	120.6	C8—C13—H13A	120.4
C6—C5—H5A	120.6	C12—C13—H13A	120.4
C5—C6—C7	120.9 (3)	C10—C14—H14C	109.5
C5—C6—H6A	119.6	C10—C14—H14B	109.5
C7—C6—H6A	119.6	H14C—C14—H14B	109.5
C2—C7—C6	119.9 (3)	C10—C14—H14A	109.5
C2—C7—H7A	120.0	H14C—C14—H14A	109.5
C6—C7—H7A	120.0	H14B—C14—H14A	109.5
C13—C8—C9	120.6 (2)	C1—N1—C8	125.9 (2)
C13—C8—N1	117.9 (2)	C1—N1—H1N	117.1
C9—C8—N1	121.5 (2)	C8—N1—H1N	117.1

O1—C1—C2—C7	147.5 (3)	C13—C8—C9—C10	0.7 (4)
N1—C1—C2—C7	−34.1 (4)	N1—C8—C9—C10	−178.0 (2)
O1—C1—C2—C3	−32.8 (4)	C8—C9—C10—C11	−0.8 (4)
N1—C1—C2—C3	145.6 (2)	C8—C9—C10—C14	179.8 (2)
C7—C2—C3—C4	2.4 (4)	C9—C10—C11—C12	0.4 (4)
C1—C2—C3—C4	−177.3 (2)	C14—C10—C11—C12	179.8 (3)
C2—C3—C4—C5	−2.9 (4)	C10—C11—C12—C13	0.1 (4)
C2—C3—C4—Cl1	176.50 (19)	C9—C8—C13—C12	−0.1 (4)
C3—C4—C5—C6	0.9 (4)	N1—C8—C13—C12	178.6 (2)
Cl1—C4—C5—C6	−178.5 (2)	C11—C12—C13—C8	−0.3 (4)
C4—C5—C6—C7	1.5 (5)	O1—C1—N1—C8	0.1 (4)
C3—C2—C7—C6	0.0 (4)	C2—C1—N1—C8	−178.2 (2)
C1—C2—C7—C6	179.7 (2)	C13—C8—N1—C1	136.5 (3)
C5—C6—C7—C2	−2.0 (4)	C9—C8—N1—C1	−44.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.10	2.938 (3)	163

Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClNO
M_r	245.70
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	9.4032 (3), 10.0963 (2), 25.9904 (7)
V (Å³)	2467.46 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.38 × 0.24 × 0.04

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini
Absorption correction	Analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.921, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	39014, 3440, 1666
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.693

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.191, 1.02
No. of reflections	3440
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.24

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2002), enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.10	2.938 (3)	163.0

Symmetry code: (i) −x+1/2, y+1/2, z.

Acknowledgements

LK and JK thank the VEGA Grant Agency of the Slovak Ministry of Education (1/0679/11) and the Research and Development Agency of Slovakia (APVV-0202–10) for financial support and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer. VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS research fellowship.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bhat, D. K. & Gowda, B. T. (2000). J. Indian Chem. Soc. 77, 279–284. CAS Google Scholar
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
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887–897. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2339. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o949. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230. CAS Google Scholar
Gowda, B. T. & Weiss, A. (1994). Z. Naturforsch. Teil A, 49, 695–702. CAS Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. 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
Shetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113–120. CAS Google Scholar