Benzyl 2-methyl-3-[(E)-(thio­phen-2-yl)methyl­idene]dithio­carbazate

Hazari, S.K.S.; Dey, B.K.; Roy, T.G.; Ganguly, B.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812012652

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1216

doi:10.1107/S1600536812012652

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Benzyl 2-methyl-3-[(E)-(thiophen-2-yl)methylidene]dithiocarbazate

Saroj K. S. Hazari,^a B. K. Dey,^a Tapashi G. Roy,^a ‡ B. Ganguly,^a Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, University of Chittagong, Chittagong 4331, Bangladesh, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 21 March 2012; accepted 23 March 2012; online 28 March 2012)

In the title compound, C₁₄H₁₄N₂S₃, the thione S atom and methyl group are syn, as are the two thioether S atoms. The molecule is twisted, the dihedral angles between the central (C₂N₂S₂) residue and the pendent 2-thienyl and phenyl rings being 21.57 (6) and 77.54 (3)°, respectively. In the crystal, molecules assemble into a three-dimensional architecture via C—H⋯π interactions, involving both the five- and six-membered rings as acceptors, as well as S⋯S interactions [3.3406 (5) Å] between centrosymmetrically related 2-thienyl rings.

Related literature

For the biological activity of related Schiff base compounds, see: Hazari et al. (2002 ). For a related structure, see: Scovill & Silverton (1980 ).

Experimental

Crystal data

C₁₄H₁₄N₂S₃
M_r = 306.45
Monoclinic, P 2₁ /n
a = 6.0585 (1) Å
b = 19.3774 (5) Å
c = 12.5769 (3) Å
β = 103.200 (2)°
V = 1437.49 (6) Å³
Z = 4
Cu Kα radiation
μ = 4.60 mm⁻¹
T = 100 K
0.15 × 0.15 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.871, T_max = 1.000
5742 measured reflections
2958 independent reflections
2746 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.080
S = 1.04
2958 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the S1,C1–C4 and C9–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯Cg1ⁱ	0.98	2.85	3.4021 (17)	117
C8—H8A⋯Cg2ⁱⁱ	0.99	2.80	3.4795 (15)	127
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+3, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812012652/hg5198sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812012652/hg5198Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812012652/hg5198Isup3.cml

checkCIF report

Comment top

As a continuation of systematic studies into the synthesis, characterization and biological activities of substituted Schiff base ligands and their metal complexes (Hazari et al., 2002), crystals of the title compound, (I), were isolated and characterized crystallographically.

In (I), Fig. 1, the conformation about the imine N1═C5 bond [1.2876 (18) Å] is E. The six atoms of the central residue (S2,S3,N1,N2,C6 & C7) are co-planar having a r.m.s. deviation for the fitted atoms of 0.0395 Å. The maximum deviations from this plane are 0.0478 (7) Å for the S2 atom and -0.0557 (7) Å for the N1 atom. The 2-thienyl and phenyl rings form dihedral angles of 21.57 (6) and 77.54 (3)°, respectively, with the central plane, indicating a twisted molecule. In a rare example of a closely related compound, an S-methyl ester, the extreme ends of the molecule are both co-planar with the central residue (Scovill & Silverton, 1980). In (I), the thione-S and methyl group are syn, as are the two thioether-S atoms.

Molecules are consolidated into a three-dimensional architecture by C—H···π interactions, involving both the five- and six-membered rings as acceptors, Table 1, as well as S1···S1ⁱ interactions [distance = 3.3406 (5) Å for symmetry operation i: 1 - x, 1 - y, -z] between centrosymmetrically related 2-thienyl rings, Fig. 2.

Related literature top

For the biological activity of related Schiff base compounds, see: Hazari et al. (2002). For a related structure, see: Scovill & Silverton (1980).

Experimental top

The title compound was isolated after a four step synthetic procedure. Synthesis of N-methyl-S-benzyldithiocarbazate: Potassium hydroxide (11.5 g), was dissolved in 90% ethanol (60 ml) and the mixture was cooled down to 273 K in an ice-bath. To this, methyl hydrazine (11.1 ml) was added slowly with mechanical stirring. A solution of carbondisulfide (12 ml) was added drop-wise from a burette with constant stirring over a period of 1 h. During this addition, the temperature of the reaction mixture was not to allowed to rise above 279 K. A yellow solution was obtained. Benzyl chloride (25 mL) was then added drop-wise with vigorous mechanical stirring. After the complete addition, the mixture was stirred for further 15 min, whereupon well formed crystals appeared. The product was separated by filtration and washed with water and recrystallized from ethanol and dried in a vacuum desiccator over silica gel. Yield: 15.75 g. M.pt: 373–375 K.

Synthesis of (I): A hot solution thiophene-2-carboxaldehyde (1.05 ml, 10 mmol) in absolute ethanol (40 ml) was mixed with a hot solution of N-methyl-S-benzyldithiocarbazate (2.12 g, 10 mmol) in the same solvent (40 ml). The mixture was refluxed for 6 h. on a water bath. After reducing a pale-red product appeared which was filtered off. This product was washed with ethanol several times (3 × 2 ml) and dried in a vacuum desiccator over silica gel. Yield: 1.55 g. M.pt: 433–435 K.

Attempted preparation of the dioxomolybdenum(VI) complex with (I): [MoO₂(acac)₂] (10 mmol) was dissolved in dry ethanol (40 ml) to which a hot solution of L (10 mmol) in dry ethanol (40 ml) was added. The mixture was refluxed for 6 h. on a water bath. After reducing the volume and standing overnight a light-blue product appeared, which was washed with ethanol for several times and dried in a vacuum desiccator over silica gel. M. pt: of product was > 493 K. Crystallization: The product was dissolved in ethanol to which half volume of petroleum ether was added (10/5 ml v/v). The solution was left for several days after which the title compound, (I), was deposited as crystals.

Structure description top

For the biological activity of related Schiff base compounds, see: Hazari et al. (2002). For a related structure, see: Scovill & Silverton (1980).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the unit-cell contents in projection down the a axis in (I). The C—H···π and S···S interactions are shown as purple and orange dashed lines, respectively.

Benzyl 2-methyl-3-[(E)-(thiophen-2-yl)methylidene]dithiocarbazate top

Crystal data top

C₁₄H₁₄N₂S₃	F(000) = 640
M_r = 306.45	D_x = 1.416 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 3411 reflections
a = 6.0585 (1) Å	θ = 3.6–76.3°
b = 19.3774 (5) Å	µ = 4.60 mm⁻¹
c = 12.5769 (3) Å	T = 100 K
β = 103.200 (2)°	Block, yellow-green
V = 1437.49 (6) Å³	0.15 × 0.15 × 0.15 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2958 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2746 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.017
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.5°, θ_min = 4.3°
ω scan	h = −7→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −21→24
T_min = 0.871, T_max = 1.000	l = −14→15
5742 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0498P)² + 0.373P] where P = (F_o² + 2F_c²)/3
2958 reflections	(Δ/σ)_max = 0.001
173 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₁₄H₁₄N₂S₃	V = 1437.49 (6) Å³
M_r = 306.45	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 6.0585 (1) Å	µ = 4.60 mm⁻¹
b = 19.3774 (5) Å	T = 100 K
c = 12.5769 (3) Å	0.15 × 0.15 × 0.15 mm
β = 103.200 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2958 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2746 reflections with I > 2σ(I)
T_min = 0.871, T_max = 1.000	R_int = 0.017
5742 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.04	Δρ_max = 0.29 e Å⁻³
2958 reflections	Δρ_min = −0.50 e Å⁻³
173 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
S1	0.38152 (6)	0.42510 (2)	0.02208 (3)	0.02374 (11)
S2	0.98715 (5)	0.412867 (18)	0.30849 (3)	0.01609 (10)
S3	1.13698 (6)	0.28550 (2)	0.44362 (3)	0.02327 (11)
N1	0.6131 (2)	0.34137 (6)	0.21795 (9)	0.0164 (2)
N2	0.7444 (2)	0.30069 (6)	0.29841 (9)	0.0173 (2)
C1	0.1243 (3)	0.43987 (9)	−0.06539 (13)	0.0309 (4)
H1	0.0995	0.4737	−0.1215	0.037*
C2	−0.0402 (3)	0.39739 (10)	−0.04503 (13)	0.0308 (4)
H2	−0.1931	0.3985	−0.0855	0.037*
C3	0.0401 (3)	0.35160 (8)	0.04254 (12)	0.0226 (3)
H3	−0.0520	0.3185	0.0677	0.027*
C4	0.2703 (2)	0.36066 (8)	0.08760 (11)	0.0176 (3)
C5	0.4082 (2)	0.32207 (7)	0.17652 (11)	0.0171 (3)
H5	0.3479	0.2825	0.2044	0.020*
C6	0.6657 (3)	0.23282 (8)	0.32401 (13)	0.0230 (3)
H6A	0.7881	0.2090	0.3753	0.035*
H6B	0.6211	0.2057	0.2568	0.035*
H6C	0.5352	0.2382	0.3571	0.035*
C7	0.9478 (2)	0.32789 (7)	0.35022 (11)	0.0161 (3)
C8	1.2618 (2)	0.43443 (8)	0.39547 (11)	0.0182 (3)
H8A	1.2569	0.4301	0.4733	0.022*
H8B	1.3797	0.4028	0.3809	0.022*
C9	1.3146 (2)	0.50761 (8)	0.36994 (11)	0.0167 (3)
C10	1.4672 (2)	0.52084 (8)	0.30438 (11)	0.0186 (3)
H10	1.5329	0.4834	0.2737	0.022*
C11	1.5239 (3)	0.58827 (8)	0.28352 (12)	0.0212 (3)
H11	1.6290	0.5967	0.2393	0.025*
C12	1.4274 (3)	0.64340 (8)	0.32713 (12)	0.0217 (3)
H12	1.4663	0.6894	0.3129	0.026*
C13	1.2733 (3)	0.63085 (8)	0.39186 (12)	0.0217 (3)
H13	1.2065	0.6684	0.4217	0.026*
C14	1.2175 (2)	0.56349 (8)	0.41276 (11)	0.0204 (3)
H14	1.1120	0.5553	0.4568	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0266 (2)	0.0239 (2)	0.01970 (19)	0.00074 (14)	0.00326 (14)	0.00408 (13)
S2	0.01503 (17)	0.01798 (18)	0.01359 (17)	−0.00058 (12)	−0.00020 (12)	0.00121 (11)
S3	0.02006 (18)	0.0231 (2)	0.0235 (2)	0.00380 (13)	−0.00161 (14)	0.00613 (14)
N1	0.0182 (6)	0.0174 (6)	0.0126 (5)	0.0008 (4)	0.0012 (4)	0.0017 (4)
N2	0.0183 (6)	0.0169 (6)	0.0151 (5)	−0.0003 (5)	0.0005 (4)	0.0031 (4)
C1	0.0414 (10)	0.0315 (9)	0.0169 (7)	0.0162 (7)	0.0005 (7)	−0.0005 (6)
C2	0.0237 (8)	0.0413 (10)	0.0227 (8)	0.0135 (7)	−0.0043 (6)	−0.0136 (7)
C3	0.0194 (7)	0.0290 (8)	0.0188 (7)	−0.0013 (6)	0.0030 (5)	−0.0106 (6)
C4	0.0180 (6)	0.0198 (7)	0.0145 (6)	−0.0010 (5)	0.0028 (5)	−0.0048 (5)
C5	0.0180 (6)	0.0176 (6)	0.0157 (6)	−0.0028 (5)	0.0041 (5)	−0.0016 (5)
C6	0.0237 (7)	0.0184 (7)	0.0254 (7)	−0.0028 (6)	0.0025 (6)	0.0057 (6)
C7	0.0160 (6)	0.0190 (6)	0.0139 (6)	0.0016 (5)	0.0044 (5)	−0.0009 (5)
C8	0.0153 (6)	0.0211 (7)	0.0162 (6)	0.0000 (5)	−0.0008 (5)	0.0001 (5)
C9	0.0136 (6)	0.0208 (7)	0.0130 (6)	0.0006 (5)	−0.0023 (5)	−0.0002 (5)
C10	0.0168 (6)	0.0221 (7)	0.0161 (6)	0.0031 (5)	0.0023 (5)	−0.0032 (5)
C11	0.0201 (7)	0.0270 (8)	0.0171 (7)	−0.0013 (6)	0.0056 (5)	0.0003 (6)
C12	0.0229 (7)	0.0215 (7)	0.0186 (7)	0.0000 (6)	0.0007 (6)	0.0014 (6)
C13	0.0234 (7)	0.0217 (7)	0.0194 (7)	0.0051 (6)	0.0038 (6)	−0.0023 (5)
C14	0.0191 (7)	0.0267 (8)	0.0161 (6)	0.0026 (6)	0.0055 (5)	−0.0007 (5)

Geometric parameters (Å, º) top

S1—C1	1.7139 (17)	C6—H6A	0.9800
S1—C4	1.7164 (15)	C6—H6B	0.9800
S2—C7	1.7610 (15)	C6—H6C	0.9800
S2—C8	1.8188 (14)	C8—C9	1.504 (2)
S3—C7	1.6594 (14)	C8—H8A	0.9900
N1—C5	1.2876 (18)	C8—H8B	0.9900
N1—N2	1.3821 (16)	C9—C10	1.3960 (19)
N2—C7	1.3615 (18)	C9—C14	1.398 (2)
N2—C6	1.4597 (18)	C10—C11	1.391 (2)
C1—C2	1.362 (3)	C10—H10	0.9500
C1—H1	0.9500	C11—C12	1.389 (2)
C2—C3	1.412 (2)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.393 (2)
C3—C4	1.3915 (19)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.388 (2)
C4—C5	1.443 (2)	C13—H13	0.9500
C5—H5	0.9500	C14—H14	0.9500

C1—S1—C4	91.75 (8)	N2—C7—S3	123.41 (11)
C7—S2—C8	101.72 (7)	N2—C7—S2	112.87 (10)
C5—N1—N2	118.12 (12)	S3—C7—S2	123.72 (8)
C7—N2—N1	115.86 (11)	C9—C8—S2	107.34 (9)
C7—N2—C6	123.27 (12)	C9—C8—H8A	110.2
N1—N2—C6	120.86 (11)	S2—C8—H8A	110.2
C2—C1—S1	112.07 (13)	C9—C8—H8B	110.2
C2—C1—H1	124.0	S2—C8—H8B	110.2
S1—C1—H1	124.0	H8A—C8—H8B	108.5
C1—C2—C3	112.96 (14)	C10—C9—C14	118.61 (14)
C1—C2—H2	123.5	C10—C9—C8	120.07 (13)
C3—C2—H2	123.5	C14—C9—C8	121.30 (13)
C4—C3—C2	111.92 (15)	C11—C10—C9	120.62 (13)
C4—C3—H3	124.0	C11—C10—H10	119.7
C2—C3—H3	124.0	C9—C10—H10	119.7
C3—C4—C5	126.83 (14)	C12—C11—C10	120.22 (14)
C3—C4—S1	111.30 (11)	C12—C11—H11	119.9
C5—C4—S1	121.87 (11)	C10—C11—H11	119.9
N1—C5—C4	119.83 (13)	C11—C12—C13	119.67 (14)
N1—C5—H5	120.1	C11—C12—H12	120.2
C4—C5—H5	120.1	C13—C12—H12	120.2
N2—C6—H6A	109.5	C14—C13—C12	119.97 (14)
N2—C6—H6B	109.5	C14—C13—H13	120.0
H6A—C6—H6B	109.5	C12—C13—H13	120.0
N2—C6—H6C	109.5	C13—C14—C9	120.90 (13)
H6A—C6—H6C	109.5	C13—C14—H14	119.6
H6B—C6—H6C	109.5	C9—C14—H14	119.6

C5—N1—N2—C7	−171.17 (12)	C6—N2—C7—S2	−175.83 (11)
C5—N1—N2—C6	9.13 (19)	C8—S2—C7—N2	177.56 (10)
C4—S1—C1—C2	0.23 (13)	C8—S2—C7—S3	−1.90 (10)
S1—C1—C2—C3	−0.11 (18)	C7—S2—C8—C9	−178.59 (9)
C1—C2—C3—C4	−0.10 (19)	S2—C8—C9—C10	−102.29 (13)
C2—C3—C4—C5	−178.82 (13)	S2—C8—C9—C14	79.22 (14)
C2—C3—C4—S1	0.27 (16)	C14—C9—C10—C11	0.9 (2)
C1—S1—C4—C3	−0.28 (12)	C8—C9—C10—C11	−177.58 (13)
C1—S1—C4—C5	178.86 (12)	C9—C10—C11—C12	−0.5 (2)
N2—N1—C5—C4	−176.07 (12)	C10—C11—C12—C13	0.0 (2)
C3—C4—C5—N1	−172.02 (13)	C11—C12—C13—C14	0.2 (2)
S1—C4—C5—N1	8.98 (19)	C12—C13—C14—C9	0.2 (2)
N1—N2—C7—S3	−176.06 (9)	C10—C9—C14—C13	−0.8 (2)
C6—N2—C7—S3	3.63 (19)	C8—C9—C14—C13	177.73 (13)
N1—N2—C7—S2	4.48 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the S1,C1–C4 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···Cg1ⁱ	0.98	2.85	3.4021 (17)	117
C8—H8A···Cg2ⁱⁱ	0.99	2.80	3.4795 (15)	127

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+3, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂S₃
M_r	306.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	6.0585 (1), 19.3774 (5), 12.5769 (3)
β (°)	103.200 (2)
V (Å³)	1437.49 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.60
Crystal size (mm)	0.15 × 0.15 × 0.15

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.871, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5742, 2958, 2746
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.080, 1.04
No. of reflections	2958
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.50

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the S1,C1–C4 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···Cg1ⁱ	0.98	2.85	3.4021 (17)	117
C8—H8A···Cg2ⁱⁱ	0.99	2.80	3.4795 (15)	127

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+3, −y+1, −z+1.

Footnotes

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

Acknowledgements

The University Grants Commission, Bangladesh, is thanked for a fellowship to BG. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hazari, S. K. S., Dey, B. K., Palit, D., Ganguli, B. & Sen, K. (2002). Ceylon J. Sci. Phys. Sci. 9, 23–30. Google Scholar
Scovill, J. P. & Silverton, J. V. (1980). J. Org. Chem. 45, 4372–4376. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 4| April 2012| Page o1216

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