(Z)-3-(4-Chloro­benz­yl)-1,5-benzothia­zepin-4(5H)-one

Lakshmanan, D.; Murugavel, S.; Selvakumar, R.; Bakthadoss, M.

doi:10.1107/S1600536812026608

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2130

https://doi.org/10.1107/S1600536812026608

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(Z)-3-(4-Chlorobenzyl)-1,5-benzothiazepin-4(5H)-one

D. Lakshmanan,^a S. Murugavel,^b ^* R. Selvakumar ^c and M. Bakthadoss ^c ‡

^aDepartment of Physics, C. Abdul Hakeem College of Engineering & Technology, Melvisharam, Vellore 632 509, India, ^bDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, and ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
^*Correspondence e-mail: smurugavel27@gmail.com

(Received 10 June 2012; accepted 12 June 2012; online 16 June 2012)

In the title compound, C₁₆H₁₂ClNOS, the seven-membered thiazepine ring adopts a distorted twisted boat conformation. The dihedral angle between the least-squares planes of the 1,5-benzothiazepine ring system and the benzene ring is 50.2 (1)°. In the crystal, pairs of N—H⋯O hydrogen bonds link centrosymmetrically related molecules into dimers, generating R₂²(8) ring motifs. The crystal packing is further stabilized by π–π interactions [centroid–centroid distance = 3.763 (2) Å].

Related literature

For the pharmaceutical properties of thiazepin derivatives, see: Tomascovic et al. (2000 ); Rajsner et al. (1971 ); Metys et al. (1965 ). For related structures, see: Sridevi et al. (2011 ); Sabari et al. (2011 ); Selvakumar et al. (2012 ). For ring-puckering parameters, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₂ClNOS
M_r = 301.78
Orthorhombic, P b c a
a = 9.0486 (3) Å
b = 9.4105 (3) Å
c = 33.4876 (10) Å
V = 2851.53 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 293 K
0.23 × 0.21 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.910, T_max = 0.941
14850 measured reflections
3099 independent reflections
2382 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.118
S = 1.03
3099 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.45 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	2.07	2.854 (2)	151
Symmetry code: (i) -x, -y, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812026608/tk5111sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812026608/tk5111Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812026608/tk5111Isup3.cml

checkCIF report

Comment top

The title compound is used as an intermediate for the synthesis of dosulepin, which is an anti-depressant of the tricyclic family. Dosulepin prevents reabsorbing of serotonin and noradrenaline in the brain, helps to prolong the mood lightening effect of any released noradrenaline and serotonin, thus relieving depression. The dibenzo[c,e]thiazepin derivatives exhibit chiroptical properties (Tomascovic et al., 2000). Dibenzo[b,e]thiazepin-5,5-dioxide derivatives possess anti-histaminic and anti-allergenic activities (Rajsner et al., 1971). Benzene thiazepin derivatives are identified as a new type of effective anti-histaminic compounds (Metys et al., 1965). In view of this biological importance, the crystal structure of the title compound has been carried out and the results are presented here.

Fig. 1. shows the seven membered thiazepine ring (N1/S1/C1/C2/C7/C8/C9) to adopt a twisted-boat conformation as indicated by puckering parameters (Cremer & Pople, 1975) QT = 1.0015 (16) Å, θ₂ = 74.1 (1)°, φ₂ = 177.3 (1)° and φ₃ = 177.6 (4)°. The dihedral angle between the benzothiazepin ring system and the benzene ring is 50.2 (1)°. The geometric parameters of the title molecule agree well with those reported for similar structures (Sridevi et al., 2011; Sabari et al., 2011).

In the crystal packing (Fig. 2), centrosymmetrically related molecules are linked by N1—H1···O1 hydrogen bonds into cyclic R₂²(8) dimers (Bernstein et al., 1995). The crystal packing (Fig. 3) is further stabilized by intermolecular π—π interactions with a Cg—Cgⁱ separation of 3.763 (1) Å [Cg is the centroid of the C2–C7 benzene ring, symmetry code as in Fig. 3].

Related literature top

For the pharmaceutical properties of thiazepin derivatives, see: Tomascovic et al. (2000); Rajsner et al. (1971); Metys et al. (1965). For related structures, see: Sridevi et al. (2011); Sabari et al. (2011); Selvakumar et al. (2012). . For ring-puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of (Z)-methyl 2-(bromomethyl)-3-(4-chlorophenyl)acrylate (2 mmol) and o-aminothiophenol (2 mmol) in the presence of potassium tert-butoxide (4.8 mmol) in dry THF (10 ml) was stirred at room temperature for 1 h. After the completion of the reaction as indicated by TLC, the reaction mixture was concentrated and the resulting crude mass was diluted with water (20 ml) and extracted with ethyl acetate (3 × 20 ml). The organic layer was washed with brine (2 × 20 ml) and dried over anhydrous sodium sulfate. The organic layer was concentrated, which successfully provided the crude final product. The final product was purified by column chromatography on silica gel to afford the title compound in good yield (43%).

Structure description top

For the pharmaceutical properties of thiazepin derivatives, see: Tomascovic et al. (2000); Rajsner et al. (1971); Metys et al. (1965). For related structures, see: Sridevi et al. (2011); Sabari et al. (2011); Selvakumar et al. (2012). . For ring-puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound showing displacement ellipsoids at the 30% probability level. H atoms are presented as a small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of the title compound showing N—H···O intermolecular hydrogen bonds (dotted lines) generating an R²₂(8) centrosymmetric dimer [Symmetry code: (i) -x, -y, -z].
	Fig. 3. A view of a π—π interaction (dotted lines) in the crystal structure of the title compound. Cg denotes centroid of the C2–C7 benzene ring [Symmetry code: (i) -x, 1 - y, -z].

(Z)-3-(4-Chlorobenzyl)-1,5-benzothiazepin-4(5H)-one top

Crystal data top

C₁₆H₁₂ClNOS	F(000) = 1248
M_r = 301.78	D_x = 1.406 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3130 reflections
a = 9.0486 (3) Å	θ = 2.4–27.0°
b = 9.4105 (3) Å	µ = 0.41 mm⁻¹
c = 33.4876 (10) Å	T = 293 K
V = 2851.53 (16) Å³	Block, colourless
Z = 8	0.23 × 0.21 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	3099 independent reflections
Radiation source: fine-focus sealed tube	2382 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 2.4°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→11
T_min = 0.910, T_max = 0.941	l = −42→29
14850 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.118	w = 1/[σ²(F_o²) + (0.0432P)² + 1.9074P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3099 reflections	Δρ_max = 0.35 e Å⁻³
182 parameters	Δρ_min = −0.45 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0057 (6)

Crystal data top

C₁₆H₁₂ClNOS	V = 2851.53 (16) Å³
M_r = 301.78	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.0486 (3) Å	µ = 0.41 mm⁻¹
b = 9.4105 (3) Å	T = 293 K
c = 33.4876 (10) Å	0.23 × 0.21 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	3099 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2382 reflections with I > 2σ(I)
T_min = 0.910, T_max = 0.941	R_int = 0.029
14850 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.03	Δρ_max = 0.35 e Å⁻³
3099 reflections	Δρ_min = −0.45 e Å⁻³
182 parameters

Special details top

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	0.0719 (3)	0.1514 (2)	0.12513 (6)	0.0476 (5)
H1A	0.0655	0.1466	0.1528	0.057*
C2	0.0392 (2)	0.3707 (2)	0.07497 (6)	0.0435 (5)
C3	0.0021 (3)	0.5128 (3)	0.08041 (7)	0.0580 (7)
H3	0.0457	0.5643	0.1010	0.070*
C4	−0.0985 (3)	0.5777 (3)	0.05567 (8)	0.0618 (7)
H4	−0.1210	0.6733	0.0592	0.074*
C5	−0.1654 (3)	0.5023 (2)	0.02586 (8)	0.0518 (6)
H5	−0.2335	0.5466	0.0092	0.062*
C6	−0.1323 (2)	0.3610 (2)	0.02049 (7)	0.0434 (5)
H6	−0.1789	0.3098	0.0004	0.052*
C7	−0.0300 (2)	0.2947 (2)	0.04485 (6)	0.0373 (4)
C8	0.0158 (2)	0.0388 (2)	0.06027 (6)	0.0399 (5)
C9	0.0015 (2)	0.0533 (2)	0.10436 (6)	0.0416 (5)
C10	−0.0895 (3)	−0.0641 (3)	0.12279 (7)	0.0555 (6)
H10A	−0.1879	−0.0612	0.1114	0.067*
H10B	−0.0457	−0.1547	0.1156	0.067*
C11	−0.1027 (3)	−0.0572 (2)	0.16758 (7)	0.0489 (6)
C12	−0.0147 (3)	−0.1404 (3)	0.19132 (8)	0.0590 (6)
H12	0.0524	−0.2022	0.1794	0.071*
C13	−0.0233 (3)	−0.1346 (3)	0.23246 (8)	0.0668 (7)
H13	0.0367	−0.1922	0.2482	0.080*
C14	−0.1208 (3)	−0.0436 (3)	0.24963 (8)	0.0639 (7)
C15	−0.2101 (3)	0.0408 (3)	0.22704 (9)	0.0733 (8)
H15	−0.2766	0.1028	0.2391	0.088*
C16	−0.2004 (3)	0.0329 (3)	0.18587 (8)	0.0664 (7)
H16	−0.2614	0.0899	0.1703	0.080*
N1	0.0078 (2)	0.15261 (18)	0.03612 (5)	0.0405 (4)
H1	0.0290	0.1363	0.0115	0.049*
O1	0.0322 (2)	−0.08062 (16)	0.04596 (4)	0.0551 (4)
S1	0.17684 (7)	0.29044 (7)	0.104528 (18)	0.0568 (2)
Cl1	−0.13112 (12)	−0.03656 (12)	0.30146 (2)	0.1046 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0518 (13)	0.0530 (13)	0.0379 (11)	−0.0069 (11)	−0.0027 (10)	0.0015 (10)
C2	0.0495 (13)	0.0381 (12)	0.0428 (11)	−0.0122 (10)	0.0066 (9)	−0.0021 (9)
C3	0.0789 (18)	0.0400 (13)	0.0552 (14)	−0.0191 (13)	0.0111 (13)	−0.0109 (11)
C4	0.0796 (19)	0.0336 (12)	0.0721 (17)	0.0004 (12)	0.0225 (15)	−0.0012 (12)
C5	0.0508 (14)	0.0379 (12)	0.0667 (15)	0.0020 (11)	0.0135 (12)	0.0109 (11)
C6	0.0418 (11)	0.0363 (12)	0.0522 (12)	−0.0045 (9)	0.0039 (10)	0.0036 (9)
C7	0.0389 (11)	0.0328 (10)	0.0400 (10)	−0.0049 (9)	0.0067 (8)	−0.0009 (8)
C8	0.0440 (12)	0.0361 (12)	0.0396 (10)	0.0032 (9)	−0.0035 (9)	−0.0018 (9)
C9	0.0469 (12)	0.0398 (12)	0.0380 (10)	0.0010 (10)	−0.0028 (9)	0.0018 (9)
C10	0.0696 (16)	0.0478 (13)	0.0492 (13)	−0.0110 (12)	−0.0046 (12)	0.0040 (11)
C11	0.0515 (14)	0.0455 (13)	0.0497 (12)	−0.0084 (11)	−0.0005 (10)	0.0095 (10)
C12	0.0615 (16)	0.0559 (15)	0.0595 (14)	0.0044 (13)	−0.0010 (12)	0.0090 (12)
C13	0.0687 (18)	0.0723 (18)	0.0593 (15)	−0.0046 (15)	−0.0117 (14)	0.0210 (14)
C14	0.0653 (17)	0.0791 (18)	0.0472 (13)	−0.0228 (15)	0.0080 (12)	0.0081 (13)
C15	0.0719 (19)	0.078 (2)	0.0698 (17)	0.0061 (16)	0.0219 (15)	0.0040 (15)
C16	0.0631 (17)	0.0714 (18)	0.0645 (16)	0.0115 (14)	0.0025 (13)	0.0179 (14)
N1	0.0527 (11)	0.0347 (9)	0.0342 (8)	0.0024 (8)	0.0011 (8)	−0.0025 (7)
O1	0.0836 (12)	0.0365 (8)	0.0453 (8)	0.0120 (8)	−0.0058 (8)	−0.0030 (7)
S1	0.0541 (4)	0.0654 (4)	0.0509 (3)	−0.0224 (3)	−0.0093 (3)	0.0030 (3)
Cl1	0.1122 (7)	0.1522 (9)	0.0494 (4)	−0.0371 (7)	0.0121 (4)	0.0051 (5)

Geometric parameters (Å, º) top

C1—C9	1.320 (3)	C8—C9	1.488 (3)
C1—S1	1.758 (2)	C9—C10	1.509 (3)
C1—H1A	0.9300	C10—C11	1.506 (3)
C2—C7	1.386 (3)	C10—H10A	0.9700
C2—C3	1.391 (3)	C10—H10B	0.9700
C2—S1	1.761 (2)	C11—C16	1.370 (4)
C3—C4	1.374 (4)	C11—C12	1.371 (3)
C3—H3	0.9300	C12—C13	1.381 (4)
C4—C5	1.366 (4)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.357 (4)
C5—C6	1.374 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.363 (4)
C6—C7	1.382 (3)	C14—Cl1	1.739 (3)
C6—H6	0.9300	C15—C16	1.383 (4)
C7—N1	1.411 (3)	C15—H15	0.9300
C8—O1	1.231 (2)	C16—H16	0.9300
C8—N1	1.344 (3)	N1—H1	0.8600

C9—C1—S1	125.10 (17)	C11—C10—H10A	108.6
C9—C1—H1A	117.5	C9—C10—H10A	108.6
S1—C1—H1A	117.5	C11—C10—H10B	108.6
C7—C2—C3	118.8 (2)	C9—C10—H10B	108.6
C7—C2—S1	120.49 (17)	H10A—C10—H10B	107.6
C3—C2—S1	120.64 (18)	C16—C11—C12	118.0 (2)
C4—C3—C2	120.6 (2)	C16—C11—C10	121.6 (2)
C4—C3—H3	119.7	C12—C11—C10	120.5 (2)
C2—C3—H3	119.7	C11—C12—C13	121.5 (3)
C5—C4—C3	120.2 (2)	C11—C12—H12	119.2
C5—C4—H4	119.9	C13—C12—H12	119.2
C3—C4—H4	119.9	C14—C13—C12	119.0 (3)
C4—C5—C6	120.1 (2)	C14—C13—H13	120.5
C4—C5—H5	120.0	C12—C13—H13	120.5
C6—C5—H5	120.0	C13—C14—C15	121.2 (3)
C5—C6—C7	120.4 (2)	C13—C14—Cl1	118.8 (2)
C5—C6—H6	119.8	C15—C14—Cl1	120.0 (2)
C7—C6—H6	119.8	C14—C15—C16	118.9 (3)
C6—C7—C2	119.92 (19)	C14—C15—H15	120.5
C6—C7—N1	117.91 (18)	C16—C15—H15	120.5
C2—C7—N1	122.02 (19)	C11—C16—C15	121.3 (3)
O1—C8—N1	119.98 (18)	C11—C16—H16	119.3
O1—C8—C9	118.70 (18)	C15—C16—H16	119.3
N1—C8—C9	121.31 (18)	C8—N1—C7	130.05 (17)
C1—C9—C8	123.0 (2)	C8—N1—H1	115.0
C1—C9—C10	124.05 (19)	C7—N1—H1	115.0
C8—C9—C10	112.71 (18)	C1—S1—C2	99.08 (10)
C11—C10—C9	114.76 (19)

C7—C2—C3—C4	−1.7 (3)	C9—C10—C11—C16	79.7 (3)
S1—C2—C3—C4	175.82 (19)	C9—C10—C11—C12	−99.3 (3)
C2—C3—C4—C5	1.3 (4)	C16—C11—C12—C13	0.1 (4)
C3—C4—C5—C6	0.0 (4)	C10—C11—C12—C13	179.1 (2)
C4—C5—C6—C7	−0.7 (3)	C11—C12—C13—C14	−0.4 (4)
C5—C6—C7—C2	0.2 (3)	C12—C13—C14—C15	0.4 (4)
C5—C6—C7—N1	−175.39 (19)	C12—C13—C14—Cl1	−179.9 (2)
C3—C2—C7—C6	1.0 (3)	C13—C14—C15—C16	0.0 (4)
S1—C2—C7—C6	−176.59 (15)	Cl1—C14—C15—C16	−179.7 (2)
C3—C2—C7—N1	176.41 (19)	C12—C11—C16—C15	0.3 (4)
S1—C2—C7—N1	−1.2 (3)	C10—C11—C16—C15	−178.7 (2)
S1—C1—C9—C8	6.9 (3)	C14—C15—C16—C11	−0.3 (4)
S1—C1—C9—C10	−179.25 (19)	O1—C8—N1—C7	170.5 (2)
O1—C8—C9—C1	135.4 (2)	C9—C8—N1—C7	−8.1 (3)
N1—C8—C9—C1	−46.0 (3)	C6—C7—N1—C8	−131.7 (2)
O1—C8—C9—C10	−39.0 (3)	C2—C7—N1—C8	52.8 (3)
N1—C8—C9—C10	139.5 (2)	C9—C1—S1—C2	58.0 (2)
C1—C9—C10—C11	3.5 (3)	C7—C2—S1—C1	−60.21 (19)
C8—C9—C10—C11	177.9 (2)	C3—C2—S1—C1	122.26 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.07	2.854 (2)	151

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂ClNOS
M_r	301.78
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	9.0486 (3), 9.4105 (3), 33.4876 (10)
V (Å³)	2851.53 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.23 × 0.21 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.910, 0.941
No. of measured, independent and observed [I > 2σ(I)] reflections	14850, 3099, 2382
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.118, 1.03
No. of reflections	3099
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.45

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.07	2.854 (2)	151

Symmetry code: (i) −x, −y, −z.

Footnotes

‡Additional correspondence author, e-mail: bhakthadoss@yahoo.com.

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

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