3-Acetyl-1-(3-methyl­phen­yl)thio­urea

Gowda, B.T.; Foro, S.; Kumar, S.

doi:10.1107/S1600536812032825

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2574

https://doi.org/10.1107/S1600536812032825

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3-Acetyl-1-(3-methylphenyl)thiourea

B. Thimme Gowda,^a ^* Sabine Foro ^b and Sharatha Kumar ^a

^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 17 July 2012; accepted 19 July 2012; online 28 July 2012)

In the crystal structure of the title compound, C₁₀H₁₂N₂OS, the conformation of the two N—H bonds are anti to each other. The amide C=O and the C=S are are also anti to each other. The N—H bond adjacent to the benzene ring is syn to the m-methyl groups. The dihedral angle between the benzene ring and the side chain [mean plane of atoms C—C(O)N—C—N; maximum deviation 0.029 (2) Å] is 14.30 (7)°. There is an intramolecular N—H⋯O hydrogen bond generating an S(6) ring motif. In the crystal, the molecules are linked via N—H⋯) hydrogen bonds, forming chains propagating along [001]. The S atom is disordered and was refined using a split model [occupancy ratio 0.56 (4):0.44 (4)].

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Alkan et al. (2011 ); Bhat & Gowda (2000 ); Bowes et al. (2003 ); Gowda et al. (2000 ); Saeed et al. (2010 ); Shahwar et al. (2012 ), of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ) and of N-chloroarylsulfonamides, see: Gowda & Ramachandra (1989 ); Jyothi & Gowda (2004 ); Shetty & Gowda (2004 ).

Experimental

Crystal data

C₁₀H₁₂N₂OS
M_r = 208.29
Monoclinic, P 2₁ /c
a = 7.6841 (9) Å
b = 14.943 (1) Å
c = 9.5358 (9) Å
β = 107.49 (1)°
V = 1044.32 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 295 K
0.48 × 0.44 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur Sapphire CCD. diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.878, T_max = 0.936
4011 measured reflections
2137 independent reflections
1789 reflections with I > 2σ(I)
R_int = 0.011

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.100
S = 1.06
2137 reflections
145 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.87 (1)	1.90 (2)	2.6536 (16)	144 (2)
N2—H2N⋯O1ⁱ	0.85 (1)	2.12 (1)	2.9564 (16)	166 (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 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: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812032825/rk2375sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812032825/rk2375Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812032825/rk2375Isup3.cml

checkCIF report

Comment top

Thiourea and its derivatives are known to exhibit a wide variety of biological activities. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Alkan et al., 2011; Bhat & Gowda, 2000; Bowes et al., 2003; Gowda et al., 2000; Saeed et al., 2010; Shahwar et al., 2012); N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-chloroarylamides (Gowda & Ramachandra, 1989; Jyothi & Gowda, 2004; Shetty & Gowda, 2004), in the present work, the crystal structure of 3-acetyl-1-(3-methylphenyl)thiourea, has been determined (Fig. 1).

The conformation of the two N–H bonds are anti to each other. The adjacent N–H bond is syn to the m-methyl group in the benzene ring, compared to the anti conformation observed between the N–H bond and the o-methyl group in the benzene ring in 3-acetyl-1-(2-methylphenyl)thiourea, I, (Shahwar et al., 2012). Furthermore, the conformation of the amide C═O and the C═S are anti to each other, similar to that observed in I.

The side chain is oriented itself with respect to the phenyl ring with the torsion angles of C2—C1–N1—C7 = -168.76 (14)° and C6—C1—N1—C7 = 14.71 (24)°. The dihedral angle between the phenyl ring and the side chain (N1/C7/N2/C8/O1/C9) is 14.30 (7)°.

The amide oxygen exhibits a bifurcated hydrogen bonding by showing the simultaneous intra- and intermolecular hydrogen bonding generating S(6) and C(4) motifs. In the crystal of the title compound, the molecules are linked via N—H···S hydrogen bonds with an R₂²(12) motif and N—H···O hydrogen bonds with a C(4) motif into a layered structure (Table 1, Fig. 2).

Related literature top

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Alkan et al. (2011); Bhat & Gowda (2000); Bowes et al. (2003); Gowda et al. (2000); Saeed et al. (2010); Shahwar et al. (2012), of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and of N-chloroarylsulfonamides, see: Gowda & Ramachandra (1989); Jyothi & Gowda (2004); Shetty & Gowda (2004).

Experimental top

3-Acetyl-1-(3-methylphenyl)thiourea was synthesized by adding a solution of acetyl chloride (0.10 mol) in acetone (30 ml) dropwise to a suspension of ammonium thiocyanate (0.10 mol) in acetone (30 ml). The reaction mixture was refluxed for 30 min. After cooling to room temperature, a solution of 3-methylaniline (0.10 mol) in acetone (10 ml) was added and refluxed for 3 h. The reaction mixture was poured into acidified cold water. The precipitated title compound was recrystallized to constant melting point from acetonitrile. The purity of the compound was checked and characterized by its infrared spectrum. The characteristic absorptions observed are 3163.7 cm^-1, 1690.0 cm^-1, 1269.5 cm^-1 and 693.3 cm^-1 for the stretching bands of N-H, C═O, C-N and C═S, respectively.

Prism like yellow single crystals used in X-ray diffraction studies were grown in acetonitrile solution by slow evaporation of the solvent at room temperature.

Structure description top

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Alkan et al. (2011); Bhat & Gowda (2000); Bowes et al. (2003); Gowda et al. (2000); Saeed et al. (2010); Shahwar et al. (2012), of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and of N-chloroarylsulfonamides, see: Gowda & Ramachandra (1989); Jyothi & Gowda (2004); Shetty & Gowda (2004).

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: 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. H atoms are presented as small spheres of arbitrary radius. Only major moiety (S1A) are presented.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

3-Acetyl-1-(3-methylphenyl)thiourea top

Crystal data top

C₁₀H₁₂N₂OS	F(000) = 440
M_r = 208.29	D_x = 1.325 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1948 reflections
a = 7.6841 (9) Å	θ = 2.6–27.9°
b = 14.943 (1) Å	µ = 0.28 mm⁻¹
c = 9.5358 (9) Å	T = 295 K
β = 107.49 (1)°	Prism, yellow
V = 1044.32 (18) Å³	0.48 × 0.44 × 0.24 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire CCD. diffractometer	2137 independent reflections
Radiation source: fine-focus sealed tube	1789 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
Rotation method data acquisition using ω and φ scans	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→8
T_min = 0.878, T_max = 0.936	k = −13→18
4011 measured reflections	l = −9→11

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0535P)² + 0.2352P] where P = (F_o² + 2F_c²)/3
2137 reflections	(Δ/σ)_max = 0.001
145 parameters	Δρ_max = 0.17 e Å⁻³
2 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₀H₁₂N₂OS	V = 1044.32 (18) Å³
M_r = 208.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.6841 (9) Å	µ = 0.28 mm⁻¹
b = 14.943 (1) Å	T = 295 K
c = 9.5358 (9) Å	0.48 × 0.44 × 0.24 mm
β = 107.49 (1)°

Data collection top

Oxford Diffraction Xcalibur Sapphire CCD. diffractometer	2137 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1789 reflections with I > 2σ(I)
T_min = 0.878, T_max = 0.936	R_int = 0.011
4011 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	2 restraints
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.17 e Å⁻³
2137 reflections	Δρ_min = −0.22 e Å⁻³
145 parameters

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	Occ. (<1)
C1	0.20722 (18)	1.01499 (9)	0.39974 (15)	0.0337 (3)
C2	0.23877 (19)	1.03395 (10)	0.54780 (17)	0.0364 (3)
H2	0.3113	0.9953	0.6178	0.044*
C3	0.1649 (2)	1.10903 (10)	0.59419 (18)	0.0413 (4)
C4	0.0590 (2)	1.16622 (11)	0.4881 (2)	0.0494 (4)
H4	0.0085	1.2171	0.5163	0.059*
C5	0.0282 (2)	1.14793 (11)	0.3408 (2)	0.0506 (4)
H5	−0.0429	1.1871	0.2710	0.061*
C6	0.1008 (2)	1.07243 (10)	0.29439 (18)	0.0428 (4)
H6	0.0785	1.0607	0.1948	0.051*
C7	0.30263 (18)	0.89953 (9)	0.24567 (15)	0.0334 (3)
C8	0.4388 (2)	0.76042 (10)	0.38195 (15)	0.0361 (3)
C9	0.5236 (3)	0.67388 (11)	0.35913 (18)	0.0520 (4)
H9A	0.6484	0.6724	0.4198	0.078*
H9B	0.5190	0.6685	0.2577	0.078*
H9C	0.4580	0.6251	0.3851	0.078*
C10	0.1971 (2)	1.12586 (13)	0.7555 (2)	0.0539 (4)
H10A	0.2948	1.0885	0.8117	0.081*
H10B	0.0880	1.1123	0.7807	0.081*
H10C	0.2289	1.1875	0.7772	0.081*
N1	0.28202 (17)	0.93305 (8)	0.36952 (13)	0.0354 (3)
H1N	0.323 (2)	0.8973 (10)	0.4440 (16)	0.042*
N2	0.37949 (17)	0.81347 (8)	0.26055 (13)	0.0344 (3)
H2N	0.391 (2)	0.7951 (11)	0.1792 (16)	0.041*
O1	0.42351 (17)	0.78202 (7)	0.50180 (11)	0.0483 (3)
S1A	0.2654 (12)	0.9501 (3)	0.0852 (7)	0.0498 (10)	0.56 (4)
S1B	0.234 (2)	0.9416 (8)	0.0776 (9)	0.0656 (16)	0.44 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0337 (7)	0.0314 (7)	0.0377 (8)	−0.0023 (6)	0.0131 (6)	−0.0005 (6)
C2	0.0353 (7)	0.0366 (8)	0.0373 (7)	−0.0019 (6)	0.0106 (6)	−0.0014 (6)
C3	0.0392 (8)	0.0389 (8)	0.0495 (9)	−0.0076 (6)	0.0191 (7)	−0.0089 (7)
C4	0.0506 (9)	0.0353 (8)	0.0676 (11)	0.0024 (7)	0.0256 (8)	−0.0049 (8)
C5	0.0517 (9)	0.0398 (9)	0.0612 (11)	0.0092 (7)	0.0182 (8)	0.0120 (8)
C6	0.0461 (8)	0.0421 (8)	0.0402 (8)	0.0039 (7)	0.0129 (7)	0.0052 (7)
C7	0.0344 (7)	0.0363 (7)	0.0299 (7)	−0.0020 (6)	0.0103 (5)	0.0014 (6)
C8	0.0471 (8)	0.0337 (7)	0.0297 (7)	−0.0007 (6)	0.0150 (6)	0.0016 (6)
C9	0.0795 (12)	0.0421 (9)	0.0397 (9)	0.0143 (8)	0.0256 (8)	0.0051 (7)
C10	0.0549 (10)	0.0569 (11)	0.0547 (10)	−0.0057 (8)	0.0238 (8)	−0.0196 (8)
N1	0.0451 (7)	0.0337 (6)	0.0273 (6)	0.0047 (5)	0.0108 (5)	0.0027 (5)
N2	0.0456 (7)	0.0344 (6)	0.0254 (6)	0.0008 (5)	0.0140 (5)	−0.0008 (5)
O1	0.0791 (8)	0.0417 (6)	0.0292 (6)	0.0119 (5)	0.0242 (5)	0.0047 (4)
S1A	0.078 (2)	0.043 (2)	0.0358 (14)	0.0165 (11)	0.0274 (16)	0.0155 (6)
S1B	0.076 (3)	0.091 (4)	0.0285 (11)	0.031 (2)	0.0134 (15)	0.0141 (17)

Geometric parameters (Å, º) top

C1—C6	1.386 (2)	C7—S1A	1.653 (5)
C1—C2	1.388 (2)	C7—S1B	1.654 (7)
C1—N1	1.4186 (18)	C8—O1	1.2268 (17)
C2—C3	1.388 (2)	C8—N2	1.3636 (18)
C2—H2	0.9300	C8—C9	1.493 (2)
C3—C4	1.386 (2)	C9—H9A	0.9600
C3—C10	1.504 (2)	C9—H9B	0.9600
C4—C5	1.379 (3)	C9—H9C	0.9600
C4—H4	0.9300	C10—H10A	0.9600
C5—C6	1.389 (2)	C10—H10B	0.9600
C5—H5	0.9300	C10—H10C	0.9600
C6—H6	0.9300	N1—H1N	0.868 (13)
C7—N1	1.3354 (18)	N2—H2N	0.853 (14)
C7—N2	1.4044 (19)

C6—C1—C2	119.71 (14)	S1A—C7—S1B	9.2 (7)
C6—C1—N1	125.04 (13)	O1—C8—N2	122.46 (13)
C2—C1—N1	115.17 (13)	O1—C8—C9	122.14 (13)
C3—C2—C1	121.73 (14)	N2—C8—C9	115.40 (13)
C3—C2—H2	119.1	C8—C9—H9A	109.5
C1—C2—H2	119.1	C8—C9—H9B	109.5
C4—C3—C2	118.18 (15)	H9A—C9—H9B	109.5
C4—C3—C10	121.56 (15)	C8—C9—H9C	109.5
C2—C3—C10	120.25 (15)	H9A—C9—H9C	109.5
C5—C4—C3	120.29 (15)	H9B—C9—H9C	109.5
C5—C4—H4	119.9	C3—C10—H10A	109.5
C3—C4—H4	119.9	C3—C10—H10B	109.5
C4—C5—C6	121.54 (16)	H10A—C10—H10B	109.5
C4—C5—H5	119.2	C3—C10—H10C	109.5
C6—C5—H5	119.2	H10A—C10—H10C	109.5
C1—C6—C5	118.55 (15)	H10B—C10—H10C	109.5
C1—C6—H6	120.7	C7—N1—C1	131.79 (12)
C5—C6—H6	120.7	C7—N1—H1N	112.6 (11)
N1—C7—N2	114.34 (12)	C1—N1—H1N	115.7 (11)
N1—C7—S1A	127.9 (2)	C8—N2—C7	129.89 (12)
N2—C7—S1A	117.58 (19)	C8—N2—H2N	119.0 (11)
N1—C7—S1B	128.8 (3)	C7—N2—H2N	111.0 (11)
N2—C7—S1B	116.6 (3)

C6—C1—C2—C3	0.6 (2)	N2—C7—N1—C1	−178.23 (13)
N1—C1—C2—C3	−176.12 (12)	S1A—C7—N1—C1	7.4 (5)
C1—C2—C3—C4	−0.8 (2)	S1B—C7—N1—C1	−4.2 (10)
C1—C2—C3—C10	178.03 (14)	C6—C1—N1—C7	14.7 (2)
C2—C3—C4—C5	0.3 (2)	C2—C1—N1—C7	−168.76 (14)
C10—C3—C4—C5	−178.41 (16)	O1—C8—N2—C7	3.5 (2)
C3—C4—C5—C6	0.2 (3)	C9—C8—N2—C7	−176.63 (14)
C2—C1—C6—C5	−0.1 (2)	N1—C7—N2—C8	−1.4 (2)
N1—C1—C6—C5	176.32 (14)	S1A—C7—N2—C8	173.5 (4)
C4—C5—C6—C1	−0.3 (2)	S1B—C7—N2—C8	−176.3 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.87 (1)	1.90 (2)	2.6536 (16)	144 (2)
N2—H2N···O1ⁱ	0.85 (1)	2.12 (1)	2.9564 (16)	166 (2)

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂N₂OS
M_r	208.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.6841 (9), 14.943 (1), 9.5358 (9)
β (°)	107.49 (1)
V (Å³)	1044.32 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.48 × 0.44 × 0.24

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire CCD.
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.878, 0.936
No. of measured, independent and observed [I > 2σ(I)] reflections	4011, 2137, 1789
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.100, 1.06
No. of reflections	2137
No. of parameters	145
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.22

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···O1	0.868 (13)	1.901 (15)	2.6536 (16)	144.0 (15)
N2—H2N···O1ⁱ	0.853 (14)	2.122 (14)	2.9564 (16)	165.8 (16)

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC–BSR one-time grant to faculty.

References

Alkan, C., Tek, Y. & Kahraman, D. (2011). Turk. J. Chem. 35, 769–777. CAS 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
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2337. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T. & Ramachandra, P. (1989). J. Chem. Soc. Perkin Trans. 2, pp. 1067–1071. CrossRef Google Scholar
Gowda, B. T., Svoboda, I. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 779–790. 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, England. Google Scholar
Saeed, A., Arshad, M. & Simpson, J. (2010). Acta Cryst. E66, o2808–o2809. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160. 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. (2004). Z. Naturforsch. Teil B, 59, 63–72. CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar