N-(3-Chloro­phen­yl)-4-methyl­benzamide hemihydrate

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

doi:10.1107/S1600536811040992

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2899

doi:10.1107/S1600536811040992

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N-(3-Chlorophenyl)-4-methylbenzamide hemihydrate

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 3 October 2011; accepted 5 October 2011; online 8 October 2011)

In the title compound, C₁₄H₁₂ClNO·0.5H₂O, the water molecule is located on a twofold axis of symmetry. The meta-Cl atom in the aniline ring is positioned anti to the N—H bond. The two benzene rings make a dihedral angle of 40.40 (11)°. The crystal structure is stabilized by intermolecular N—H⋯O and O—H⋯O hydrogen bonds, which link the molecules into chains along the a axis.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ). For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003 ); Gowda et al. (1999 ); Rodrigues et al. (2011 ); 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-arylsulfonamides, see: Gowda & Shetty (2004 ).

Experimental

Crystal data

C₁₄H₁₂ClNO·0.5H₂O
M_r = 254.71
Monoclinic, C 2/c
a = 7.8078 (3) Å
b = 12.1704 (5) Å
c = 27.1217 (9) Å
β = 93.564 (3)°
V = 2572.24 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 298 K
0.76 × 0.34 × 0.02 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 from Clark & Reid (1995 )] T_min = 0.890, T_max = 0.993
3313 measured reflections
3313 independent reflections
1943 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.142
S = 1.01
3313 reflections
169 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 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⋯O2ⁱ	0.86 (2)	2.11 (2)	2.947 (2)	167 (2)
O2—H2O⋯O1ⁱⁱ	0.84 (2)	1.92 (2)	2.7630 (19)	176 (3)
Symmetry codes: (i) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

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: DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811040992/bq2309sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811040992/bq2309Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811040992/bq2309Isup3.cml

checkCIF report

Comment top

The amide and sulfonamide moieties are the constituents of many biologically significant compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 1999; Saeed et al., 2010; Rodrigues et al., 2011), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloro-arylsulfonamides (Gowda & Shetty, 2004), in the present work, the crystal structure of N-(3-Chlorophenyl)- 4-methylbenzamide (I) has been determined (Fig.1).

In (I), the water molecule is in special position and connects the different molecules of the compound. Further, the meta-Cl atom 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 are anti to each other, similar to that observed in N-(2-chlorophenyl)- 4-methylbenzamide (Rodrigues et al., 2011). The C(benzoyl)—NH—C(O)—C(anilino) torsional angle is -172.65 (18)°.

The packing of molecules linked by N1—H1N···O2 and O2—H2O···O1 hydrogen bonds into infinite chains is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Gowda et al. (2003). For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (1999); Rodrigues et al. (2011); 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-arylsulfonamides, see: Gowda & Shetty (2004).

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 colourless single crystals of the title compound were obtained by slow evaporation of an 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: enCIFer (Allen et al., 2004).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of the title compound. Molecular chains are generated by N—H···O and O—H···O hydrogen bonds which are shown by dashed lines. H atoms not involved in intermolecular bonding have been omitted.

N-(3-Chlorophenyl)-4-methylbenzamide hemihydrate top

Crystal data top

C₁₄H₁₂ClNO·0.5H₂O	F(000) = 1064
M_r = 254.71	D_x = 1.315 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 21518 reflections
a = 7.8078 (3) Å	θ = 3.5–29.4°
b = 12.1704 (5) Å	µ = 0.29 mm⁻¹
c = 27.1217 (9) Å	T = 298 K
β = 93.564 (3)°	Plate, colorless
V = 2572.24 (17) Å³	0.76 × 0.34 × 0.02 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3313 independent reflections
Radiation source: fine-focus sealed tube	1943 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 10.4340 pixels mm^-1	θ_max = 29.5°, θ_min = 3.5°
ω scans	h = −10→10
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]	k = −16→16
T_min = 0.890, T_max = 0.993	l = −36→33
3313 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.049P)² + 2.1399P] where P = (F_o² + 2F_c²)/3
3313 reflections	(Δ/σ)_max < 0.001
169 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₄H₁₂ClNO·0.5H₂O	V = 2572.24 (17) Å³
M_r = 254.71	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 7.8078 (3) Å	µ = 0.29 mm⁻¹
b = 12.1704 (5) Å	T = 298 K
c = 27.1217 (9) Å	0.76 × 0.34 × 0.02 mm
β = 93.564 (3)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3313 independent reflections
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]	1943 reflections with I > 2σ(I)
T_min = 0.890, T_max = 0.993	R_int = 0.040
3313 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.31 e Å⁻³
3313 reflections	Δρ_min = −0.39 e Å⁻³
169 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	Occ. (<1)
C1	0.2326 (2)	0.60328 (17)	0.27192 (7)	0.0465 (5)
C2	0.2647 (2)	0.63298 (17)	0.21979 (7)	0.0452 (5)
C3	0.3261 (2)	0.73485 (18)	0.20695 (7)	0.0502 (5)
H3A	0.3404	0.7896	0.2307	0.060*
C4	0.3664 (3)	0.7558 (2)	0.15888 (8)	0.0589 (6)
H4A	0.4091	0.8245	0.1510	0.071*
C5	0.3444 (3)	0.6770 (2)	0.12247 (8)	0.0606 (6)
C6	0.2797 (3)	0.5762 (2)	0.13527 (8)	0.0639 (7)
H6A	0.2615	0.5226	0.1111	0.077*
C7	0.2413 (3)	0.55318 (19)	0.18318 (8)	0.0566 (6)
H7A	0.1998	0.4842	0.1910	0.068*
C8	0.3887 (4)	0.7009 (3)	0.07011 (9)	0.0856 (10)
H8C	0.423 (2)	0.6369 (10)	0.0554 (3)	0.103*	0.50
H8B	0.476 (2)	0.7518 (13)	0.07042 (9)	0.103*	0.50
H8A	0.2934 (16)	0.7286 (15)	0.0525 (3)	0.103*	0.50
H8F	0.424 (2)	0.6373 (10)	0.0552 (3)	0.103*	0.50
H8E	0.476 (2)	0.7517 (13)	0.07049 (9)	0.103*	0.50
H8D	0.2940 (16)	0.7288 (15)	0.0523 (3)	0.103*	0.50
C9	0.1532 (2)	0.68527 (16)	0.35142 (7)	0.0427 (5)
C10	0.1959 (3)	0.59716 (19)	0.38225 (7)	0.0528 (5)
H10A	0.2417	0.5330	0.3699	0.063*
C11	0.1685 (3)	0.6074 (2)	0.43183 (8)	0.0582 (6)
C12	0.1025 (3)	0.6999 (2)	0.45181 (8)	0.0623 (6)
H12A	0.0851	0.7040	0.4854	0.075*
C13	0.0623 (3)	0.7868 (2)	0.42085 (8)	0.0634 (6)
H13A	0.0179	0.8509	0.4337	0.076*
C14	0.0871 (3)	0.78007 (18)	0.37099 (8)	0.0532 (5)
H14A	0.0592	0.8395	0.3505	0.064*
N1	0.1767 (2)	0.68533 (15)	0.30024 (6)	0.0446 (4)
H1N	0.142 (3)	0.7439 (19)	0.2852 (8)	0.051 (6)*
O1	0.2586 (2)	0.50930 (12)	0.28769 (6)	0.0653 (5)
O2	0.5000	0.37191 (16)	0.2500	0.0465 (5)
H2O	0.573 (3)	0.412 (2)	0.2370 (9)	0.077 (8)*
Cl1	0.22644 (12)	0.49860 (7)	0.47115 (3)	0.0998 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0489 (11)	0.0454 (12)	0.0457 (11)	0.0082 (9)	0.0073 (9)	−0.0017 (9)
C2	0.0453 (11)	0.0496 (12)	0.0410 (11)	0.0132 (9)	0.0041 (8)	0.0001 (9)
C3	0.0487 (11)	0.0564 (13)	0.0457 (12)	0.0040 (10)	0.0052 (9)	−0.0042 (10)
C4	0.0569 (13)	0.0665 (15)	0.0544 (14)	0.0037 (11)	0.0113 (10)	0.0077 (11)
C5	0.0581 (13)	0.0809 (18)	0.0433 (12)	0.0259 (12)	0.0080 (10)	0.0040 (12)
C6	0.0819 (16)	0.0681 (17)	0.0413 (12)	0.0271 (13)	0.0003 (11)	−0.0106 (11)
C7	0.0728 (14)	0.0489 (13)	0.0480 (12)	0.0141 (11)	0.0024 (10)	−0.0052 (10)
C8	0.0910 (19)	0.119 (3)	0.0488 (14)	0.0294 (18)	0.0182 (13)	0.0114 (15)
C9	0.0407 (10)	0.0486 (12)	0.0393 (10)	−0.0001 (9)	0.0055 (8)	−0.0030 (9)
C10	0.0592 (13)	0.0557 (13)	0.0443 (12)	0.0075 (10)	0.0083 (9)	−0.0005 (10)
C11	0.0606 (13)	0.0699 (16)	0.0444 (12)	0.0025 (11)	0.0071 (10)	0.0079 (11)
C12	0.0630 (14)	0.0837 (18)	0.0413 (12)	−0.0007 (12)	0.0118 (10)	−0.0086 (12)
C13	0.0734 (15)	0.0627 (15)	0.0552 (14)	0.0057 (12)	0.0145 (11)	−0.0164 (12)
C14	0.0607 (13)	0.0501 (13)	0.0494 (12)	0.0046 (10)	0.0080 (10)	−0.0047 (10)
N1	0.0525 (10)	0.0426 (10)	0.0391 (9)	0.0097 (8)	0.0062 (7)	0.0009 (8)
O1	0.0982 (12)	0.0471 (9)	0.0530 (9)	0.0223 (8)	0.0233 (8)	0.0052 (7)
O2	0.0543 (12)	0.0347 (11)	0.0513 (12)	0.000	0.0100 (10)	0.000
Cl1	0.1414 (7)	0.1010 (6)	0.0589 (4)	0.0332 (5)	0.0211 (4)	0.0276 (4)

Geometric parameters (Å, º) top

C1—O1	1.233 (2)	C8—H8F	0.9223
C1—N1	1.349 (2)	C8—H8E	0.9222
C1—C2	1.495 (3)	C8—H8D	0.9223
C2—C3	1.382 (3)	C9—C14	1.383 (3)
C2—C7	1.393 (3)	C9—C10	1.388 (3)
C3—C4	1.384 (3)	C9—N1	1.411 (2)
C3—H3A	0.9300	C10—C11	1.380 (3)
C4—C5	1.379 (3)	C10—H10A	0.9300
C4—H4A	0.9300	C11—C12	1.365 (3)
C5—C6	1.380 (4)	C11—Cl1	1.742 (2)
C5—C8	1.511 (3)	C12—C13	1.374 (3)
C6—C7	1.380 (3)	C12—H12A	0.9300
C6—H6A	0.9300	C13—C14	1.380 (3)
C7—H7A	0.9300	C13—H13A	0.9300
C8—H8C	0.9223	C14—H14A	0.9300
C8—H8B	0.9223	N1—H1N	0.86 (2)
C8—H8A	0.9223	O2—H2O	0.84 (2)

O1—C1—N1	122.76 (19)	C5—C8—H8E	109.4
O1—C1—C2	121.22 (18)	H8C—C8—H8E	109.4
N1—C1—C2	116.01 (18)	H8A—C8—H8E	109.6
C3—C2—C7	118.55 (19)	H8F—C8—H8E	109.1
C3—C2—C1	122.43 (18)	C5—C8—H8D	109.9
C7—C2—C1	118.9 (2)	H8C—C8—H8D	109.4
C2—C3—C4	120.4 (2)	H8B—C8—H8D	109.1
C2—C3—H3A	119.8	H8F—C8—H8D	109.2
C4—C3—H3A	119.8	H8E—C8—H8D	109.2
C5—C4—C3	121.4 (2)	C14—C9—C10	119.64 (18)
C5—C4—H4A	119.3	C14—C9—N1	116.84 (18)
C3—C4—H4A	119.3	C10—C9—N1	123.51 (18)
C4—C5—C6	118.0 (2)	C11—C10—C9	118.1 (2)
C4—C5—C8	120.9 (3)	C11—C10—H10A	120.9
C6—C5—C8	121.1 (2)	C9—C10—H10A	120.9
C5—C6—C7	121.4 (2)	C12—C11—C10	123.1 (2)
C5—C6—H6A	119.3	C12—C11—Cl1	118.31 (17)
C7—C6—H6A	119.3	C10—C11—Cl1	118.56 (19)
C6—C7—C2	120.2 (2)	C11—C12—C13	118.0 (2)
C6—C7—H7A	119.9	C11—C12—H12A	121.0
C2—C7—H7A	119.9	C13—C12—H12A	121.0
C5—C8—H8C	109.5	C12—C13—C14	120.8 (2)
C5—C8—H8B	109.5	C12—C13—H13A	119.6
H8C—C8—H8B	109.5	C14—C13—H13A	119.6
C5—C8—H8A	109.5	C13—C14—C9	120.2 (2)
H8C—C8—H8A	109.5	C13—C14—H14A	119.9
H8B—C8—H8A	109.5	C9—C14—H14A	119.9
C5—C8—H8F	110.0	C1—N1—C9	128.76 (18)
H8B—C8—H8F	109.2	C1—N1—H1N	116.7 (14)
H8A—C8—H8F	109.3	C9—N1—H1N	114.3 (14)

O1—C1—C2—C3	−144.7 (2)	C14—C9—C10—C11	0.7 (3)
N1—C1—C2—C3	34.3 (3)	N1—C9—C10—C11	179.3 (2)
O1—C1—C2—C7	31.5 (3)	C9—C10—C11—C12	−0.3 (3)
N1—C1—C2—C7	−149.48 (19)	C9—C10—C11—Cl1	−178.47 (16)
C7—C2—C3—C4	−1.2 (3)	C10—C11—C12—C13	−0.3 (4)
C1—C2—C3—C4	174.99 (18)	Cl1—C11—C12—C13	177.90 (18)
C2—C3—C4—C5	0.9 (3)	C11—C12—C13—C14	0.5 (4)
C3—C4—C5—C6	0.4 (3)	C12—C13—C14—C9	−0.1 (3)
C3—C4—C5—C8	179.9 (2)	C10—C9—C14—C13	−0.5 (3)
C4—C5—C6—C7	−1.5 (3)	N1—C9—C14—C13	−179.24 (19)
C8—C5—C6—C7	179.0 (2)	O1—C1—N1—C9	6.4 (3)
C5—C6—C7—C2	1.2 (3)	C2—C1—N1—C9	−172.65 (18)
C3—C2—C7—C6	0.2 (3)	C14—C9—N1—C1	−177.4 (2)
C1—C2—C7—C6	−176.16 (19)	C10—C9—N1—C1	3.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.86 (2)	2.11 (2)	2.947 (2)	167 (2)
O2—H2O···O1ⁱⁱ	0.84 (2)	1.92 (2)	2.7630 (19)	176 (3)

Symmetry codes: (i) x−1/2, y+1/2, z; (ii) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClNO·0.5H₂O
M_r	254.71
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	7.8078 (3), 12.1704 (5), 27.1217 (9)
β (°)	93.564 (3)
V (Å³)	2572.24 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.76 × 0.34 × 0.02

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]
T_min, T_max	0.890, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	3313, 3313, 1943
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.693

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.142, 1.01
No. of reflections	3313
No. of parameters	169
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.39

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···O2ⁱ	0.86 (2)	2.11 (2)	2.947 (2)	167 (2)
O2—H2O···O1ⁱⁱ	0.84 (2)	1.92 (2)	2.7630 (19)	176 (3)

Symmetry codes: (i) x−1/2, y+1/2, z; (ii) −x+1, y, −z+1/2.

Acknowledgements

LK and JK thank the VEGA Grant Agency of Slovak Ministry of Education 1/0679/11, the Research and Development Agency of Slovakia (APVV-0202–10) for financial support of this work 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 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 CrossRef CAS IUCr Journals 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., Bhat, D. K., Fuess, H. & Weiss, A. (1999). Z. Naturforsch. Teil A, 54, 679–684. 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., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230. CAS Google Scholar
Gowda, B. T. & Shetty, M. (2004). J. Phys. Org. Chem. 17, 848–864. Web of Science CrossRef CAS Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Rodrigues, V. Z., Herich, P., Gowda, B. T. & Kožíšek, J. (2011). Acta Cryst. E67, o2767. 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
Shetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113–120. CAS Google Scholar