Benzyl 3-(2-methyl­phen­yl)dithio­carbazate

Tayamon, S.; Ravoof, T.B.S.A.; Tahir, M.I.M.; Crouse, K.A.; Tiekink, E.R.T.

doi:10.1107/S160053681201567X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1402

doi:10.1107/S160053681201567X

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Benzyl 3-(2-methylphenyl)dithiocarbazate

Shahedeh Tayamon,^a Thahira Begum S. A. Ravoof,^a Mohamed Ibrahim Mohamed Tahir,^a Karen A. Crouse ^a ‡ and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 10 April 2012; accepted 11 April 2012; online 18 April 2012)

In the title compound, C₁₅H₁₆N₂S₂, the central C₂N₂S₂ unit is essentially planar (r.m.s. deviation = 0.047 Å) and forms dihedral angles of 68.26 (4) and 65.99 (4)° with the phenyl and benzene rings, respectively, indicating a twisted molecule. Supramolecular chains with a step topology and propagating along [100] feature in the crystal packing, mediated through N—H⋯S hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C—H⋯π interactions.

Related literature

For background to the coordination chemistry and bio-activity of hydrazinecarbodithioates, see: Khoo et al. (2005 ); Chan et al. (2008 ); Ravoof et al. (2010 ). For related structures, see: Paulus et al. (2011 ); Manan et al. (2012 ). For the synthesis, see: Tarafder et al. (2002 ).

Experimental

Crystal data

C₁₅H₁₆N₂S₂
M_r = 288.42
Monoclinic, P 2₁ /n
a = 5.7000 (1) Å
b = 11.0136 (2) Å
c = 22.7545 (4) Å
β = 95.198 (2)°
V = 1422.60 (4) Å³
Z = 4
Cu Kα radiation
μ = 3.27 mm⁻¹
T = 100 K
0.22 × 0.14 × 0.08 mm

Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.63, T_max = 0.77
15011 measured reflections
2725 independent reflections
2560 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.097
S = 1.03
2725 reflections
179 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C9–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯S2ⁱ	0.88 (1)	2.50 (1)	3.3625 (14)	169 (2)
N2—H2n⋯S2ⁱⁱ	0.88 (1)	2.79 (2)	3.5919 (13)	152 (1)
C11—H11⋯Cg1ⁱⁱⁱ	0.95	2.98	3.8594 (18)	155
C5—H5⋯Cg2^iv	0.95	2.84	3.7005 (18)	151
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x+1, y, z; (iii) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) x-1, y+1, z.

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/S160053681201567X/hg5209sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201567X/hg5209Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201567X/hg5209Isup3.cml

checkCIF report

Comment top

The study of hydrazinecarbodithioate derivatives, their coordination chemistry and bio-activities has been carried out in our laboratory for a number of years (Khoo et al. 2005; Chan et al. 2008; Ravoof et al., 2010; Paulus et al., 2011; Manan et al., 2012). In our efforts to expand the scope of these investigations, the title compound (I) was synthesized and characterized crystallographically.

In (I), Fig. 1, the central moiety is essentially planar with a r.m.s. deviation of the fitted atoms (S1,S2,N1,N2,C1 and C8) of 0.047 Å with the maximum deviations being 0.0709 (8) and -0.0711 (11) Å for the N2 and N1 atoms, respectively. The phenyl and o-tolyl rings lie out of this plane forming dihedral angles of 68.26 (4) and 65.99 (4)°, respectively. The o-tolyl ring is orientated to one side of the central plane as seen in the C8—N1—N2—C9 torsion angle of 111.24 (16)°, whereas the plane through the central atoms almost bisects the phenyl ring with the C8—S1—C1—C2 torsion angle being 176.89 (11)°.

The most prominent feature of the crystal packing is the formation of supramolecular chains along [100]. These are mediated through N—H···S hydrogen bonds involving the thione-S2 atom, Table 1. Thus, centrosymmetrically related molecules are connected into dimeric aggregates via eight-membered {···HNCS}₂ synthons. These are connected to translationally related dimeric aggregates via weaker N—H···S hydrogen bonds leading to 10-membered {···HNNH···S}₂ synthons. The chain has a step topology and comprises alternating {···HNCS}₂ and {···HNNH···S}₂ synthons, Fig. 2. The chains are consolidated into a three-dimensional architecture by C—H···π interactions, Fig. 3 and Table 1.

Related literature top

For background to the coordination chemistry and bio-activity of hydrazinecarbodithioates, see: Khoo et al. (2005); Chan et al. (2008); Ravoof et al. (2010). For related structures, see: Paulus et al. (2011); Manan et al. (2012). For the synthesis, see: Tarafder et al. (2002).

Experimental top

The compound was prepared by adapting the synthetic procedure for S-benzyldithiocarbazate (Tarafder et al., 2002). o-Tolylhydrazine hydrochloride (0.1 mol) in absolute ethanol (70 ml) was added to a solution of potassium hydroxide (0.1 mol) in absolute ethanol (40 ml). The mixture was cooled in an ice-salt bath and carbon disulfide (0.1 mol) was added drop-wise with constant stirring over one hour, during which a yellow-orange solution was formed. The temperature of reaction was kept below 278 K. Benzyl chloride (0.1 mol) was added drop-wise to the above solution with vigorous stirring while continuing to maintain the temperature below 278 K. The pale product was filtered off, dried briefly in a vacuum desiccator over anhydrous silica gel, recrystallized from absolute ethanol and kept in a freezer overnight. Dark-yellow crystals were grown from its ethanol solution. Yield 89%. M.pt: 392 K. Anal. Found (Calc.): C, 62.03 (62.46); H, 5.34 (5.59); N: 10.26 (9.71)%.

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 supramolecular chain in (I) mediated by N—H···S hydrogen bonding, shown as blue dashed lines.
	Fig. 3. A view in projection down the a axis of the unit-cell contents for (I). The N—H···S hydrogen bonding and C—H···π interactions are shown as blue and purple dashed lines, respectively.

Benzyl 3-(2-methylphenyl)dithiocarbazate top

Crystal data top

C₁₅H₁₆N₂S₂	F(000) = 608
M_r = 288.42	D_x = 1.347 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 8863 reflections
a = 5.7000 (1) Å	θ = 4–71°
b = 11.0136 (2) Å	µ = 3.27 mm⁻¹
c = 22.7545 (4) Å	T = 100 K
β = 95.198 (2)°	Prism, dark-yellow
V = 1422.60 (4) Å³	0.22 × 0.14 × 0.08 mm
Z = 4

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	2725 independent reflections
Radiation source: fine-focus sealed tube	2560 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 16.1952 pixels mm^-1	θ_max = 71.5°, θ_min = 3.9°
ω/2θ scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −13→13
T_min = 0.63, T_max = 0.77	l = −27→25
15011 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0646P)² + 0.6201P] where P = (F_o² + 2F_c²)/3
2725 reflections	(Δ/σ)_max = 0.001
179 parameters	Δρ_max = 0.44 e Å⁻³
2 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₅H₁₆N₂S₂	V = 1422.60 (4) Å³
M_r = 288.42	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 5.7000 (1) Å	µ = 3.27 mm⁻¹
b = 11.0136 (2) Å	T = 100 K
c = 22.7545 (4) Å	0.22 × 0.14 × 0.08 mm
β = 95.198 (2)°

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	2725 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2560 reflections with I > 2σ(I)
T_min = 0.63, T_max = 0.77	R_int = 0.022
15011 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	2 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.44 e Å⁻³
2725 reflections	Δρ_min = −0.23 e Å⁻³
179 parameters

Special details top

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 > 2σ(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	0.96691 (6)	0.83305 (3)	0.582743 (16)	0.02154 (13)
S2	0.73047 (7)	0.64766 (4)	0.498745 (16)	0.02497 (14)
N1	1.1403 (2)	0.62113 (12)	0.56054 (6)	0.0234 (3)
H1n	1.153 (3)	0.5503 (11)	0.5436 (8)	0.028*
N2	1.3086 (2)	0.65256 (12)	0.60680 (6)	0.0226 (3)
H2n	1.446 (2)	0.6572 (17)	0.5924 (8)	0.027*
C1	0.6928 (3)	0.90389 (14)	0.55250 (7)	0.0247 (3)
H1A	0.6944	0.9153	0.5094	0.030*
H1B	0.5571	0.8516	0.5597	0.030*
C2	0.6713 (3)	1.02493 (14)	0.58237 (6)	0.0216 (3)
C3	0.8217 (3)	1.12038 (16)	0.57225 (7)	0.0277 (4)
H3	0.9444	1.1086	0.5472	0.033*
C4	0.7947 (3)	1.23226 (16)	0.59816 (8)	0.0314 (4)
H4	0.8989	1.2967	0.5908	0.038*
C5	0.6166 (3)	1.25144 (15)	0.63490 (7)	0.0285 (4)
H5	0.5978	1.3288	0.6524	0.034*
C6	0.4669 (3)	1.15700 (15)	0.64578 (8)	0.0279 (4)
H6	0.3445	1.1693	0.6709	0.033*
C7	0.4950 (3)	1.04384 (15)	0.62004 (7)	0.0252 (3)
H7	0.3931	0.9789	0.6282	0.030*
C8	0.9545 (3)	0.69201 (14)	0.54650 (6)	0.0206 (3)
C9	1.3110 (3)	0.57463 (14)	0.65724 (7)	0.0211 (3)
C10	1.4934 (3)	0.59097 (14)	0.70252 (7)	0.0231 (3)
C11	1.4978 (3)	0.51509 (15)	0.75165 (7)	0.0272 (3)
H11	1.6205	0.5243	0.7825	0.033*
C12	1.3278 (3)	0.42639 (16)	0.75675 (7)	0.0294 (4)
H12	1.3361	0.3745	0.7902	0.035*
C13	1.1459 (3)	0.41438 (16)	0.71253 (7)	0.0288 (4)
H13	1.0267	0.3553	0.7161	0.035*
C14	1.1371 (3)	0.48843 (15)	0.66296 (7)	0.0250 (3)
H14	1.0114	0.4800	0.6328	0.030*
C15	1.6766 (3)	0.68749 (16)	0.69763 (7)	0.0288 (4)
H15A	1.7773	0.6925	0.7348	0.043*
H15B	1.5991	0.7659	0.6894	0.043*
H15C	1.7730	0.6670	0.6655	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0220 (2)	0.0224 (2)	0.0195 (2)	0.00052 (13)	−0.00217 (14)	−0.00249 (13)
S2	0.0232 (2)	0.0274 (2)	0.0232 (2)	−0.00015 (14)	−0.00370 (15)	−0.00584 (14)
N1	0.0266 (7)	0.0216 (6)	0.0210 (6)	0.0004 (5)	−0.0032 (5)	−0.0029 (5)
N2	0.0217 (7)	0.0245 (7)	0.0207 (7)	−0.0005 (5)	−0.0028 (5)	0.0004 (5)
C1	0.0217 (8)	0.0261 (8)	0.0253 (8)	0.0019 (6)	−0.0035 (6)	−0.0019 (6)
C2	0.0209 (7)	0.0242 (8)	0.0188 (7)	0.0017 (6)	−0.0030 (5)	0.0008 (6)
C3	0.0288 (8)	0.0312 (8)	0.0241 (8)	−0.0025 (7)	0.0065 (6)	−0.0002 (6)
C4	0.0372 (10)	0.0252 (8)	0.0323 (9)	−0.0060 (7)	0.0055 (7)	0.0007 (7)
C5	0.0320 (9)	0.0256 (8)	0.0268 (8)	0.0048 (6)	−0.0037 (6)	−0.0036 (6)
C6	0.0214 (8)	0.0359 (9)	0.0263 (8)	0.0047 (6)	0.0019 (6)	−0.0026 (7)
C7	0.0207 (7)	0.0287 (8)	0.0260 (8)	−0.0021 (6)	0.0003 (6)	0.0016 (6)
C8	0.0230 (7)	0.0233 (7)	0.0157 (7)	−0.0025 (6)	0.0026 (5)	0.0008 (6)
C9	0.0217 (7)	0.0214 (7)	0.0203 (7)	0.0037 (6)	0.0030 (6)	−0.0018 (6)
C10	0.0218 (8)	0.0269 (8)	0.0208 (7)	0.0033 (6)	0.0024 (6)	−0.0049 (6)
C11	0.0255 (8)	0.0366 (9)	0.0192 (7)	0.0045 (7)	0.0000 (6)	−0.0025 (6)
C12	0.0343 (9)	0.0339 (9)	0.0205 (8)	0.0048 (7)	0.0062 (6)	0.0034 (6)
C13	0.0283 (8)	0.0298 (8)	0.0289 (8)	−0.0017 (7)	0.0067 (6)	0.0010 (7)
C14	0.0234 (8)	0.0263 (8)	0.0247 (8)	0.0004 (6)	−0.0004 (6)	−0.0019 (6)
C15	0.0249 (8)	0.0355 (9)	0.0254 (8)	−0.0024 (7)	−0.0016 (6)	−0.0024 (7)

Geometric parameters (Å, º) top

S1—C8	1.7571 (15)	C5—H5	0.9500
S1—C1	1.8247 (16)	C6—C7	1.392 (2)
S2—C8	1.6729 (15)	C6—H6	0.9500
N1—C8	1.331 (2)	C7—H7	0.9500
N1—N2	1.4020 (17)	C9—C14	1.387 (2)
N1—H1n	0.877 (9)	C9—C10	1.407 (2)
N2—C9	1.432 (2)	C10—C11	1.394 (2)
N2—H2n	0.878 (9)	C10—C15	1.501 (2)
C1—C2	1.506 (2)	C11—C12	1.388 (2)
C1—H1A	0.9900	C11—H11	0.9500
C1—H1B	0.9900	C12—C13	1.384 (2)
C2—C3	1.389 (2)	C12—H12	0.9500
C2—C7	1.394 (2)	C13—C14	1.389 (2)
C3—C4	1.381 (2)	C13—H13	0.9500
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.389 (3)	C15—H15A	0.9800
C4—H4	0.9500	C15—H15B	0.9800
C5—C6	1.382 (2)	C15—H15C	0.9800

C8—S1—C1	101.79 (7)	C2—C7—H7	119.7
C8—N1—N2	120.74 (13)	C6—C7—H7	119.7
C8—N1—H1n	120.8 (13)	N1—C8—S2	121.91 (12)
N2—N1—H1n	118.2 (13)	N1—C8—S1	114.11 (11)
N1—N2—C9	114.19 (12)	S2—C8—S1	123.98 (9)
N1—N2—H2n	108.0 (13)	C14—C9—C10	120.37 (14)
C9—N2—H2n	112.9 (13)	C14—C9—N2	122.02 (14)
C2—C1—S1	108.06 (10)	C10—C9—N2	117.57 (14)
C2—C1—H1A	110.1	C11—C10—C9	117.97 (15)
S1—C1—H1A	110.1	C11—C10—C15	121.44 (14)
C2—C1—H1B	110.1	C9—C10—C15	120.59 (14)
S1—C1—H1B	110.1	C12—C11—C10	121.78 (15)
H1A—C1—H1B	108.4	C12—C11—H11	119.1
C3—C2—C7	118.62 (15)	C10—C11—H11	119.1
C3—C2—C1	121.22 (14)	C13—C12—C11	119.28 (15)
C7—C2—C1	120.15 (14)	C13—C12—H12	120.4
C4—C3—C2	120.69 (15)	C11—C12—H12	120.4
C4—C3—H3	119.7	C12—C13—C14	120.25 (16)
C2—C3—H3	119.7	C12—C13—H13	119.9
C3—C4—C5	120.58 (16)	C14—C13—H13	119.9
C3—C4—H4	119.7	C9—C14—C13	120.29 (15)
C5—C4—H4	119.7	C9—C14—H14	119.9
C6—C5—C4	119.37 (15)	C13—C14—H14	119.9
C6—C5—H5	120.3	C10—C15—H15A	109.5
C4—C5—H5	120.3	C10—C15—H15B	109.5
C5—C6—C7	120.12 (16)	H15A—C15—H15B	109.5
C5—C6—H6	119.9	C10—C15—H15C	109.5
C7—C6—H6	119.9	H15A—C15—H15C	109.5
C2—C7—C6	120.61 (15)	H15B—C15—H15C	109.5

C8—N1—N2—C9	111.24 (16)	C1—S1—C8—S2	−1.24 (12)
C8—S1—C1—C2	176.89 (11)	N1—N2—C9—C14	−9.7 (2)
S1—C1—C2—C3	68.74 (16)	N1—N2—C9—C10	172.43 (13)
S1—C1—C2—C7	−112.65 (14)	C14—C9—C10—C11	2.4 (2)
C7—C2—C3—C4	−1.1 (2)	N2—C9—C10—C11	−179.66 (14)
C1—C2—C3—C4	177.55 (15)	C14—C9—C10—C15	−177.54 (14)
C2—C3—C4—C5	0.0 (3)	N2—C9—C10—C15	0.4 (2)
C3—C4—C5—C6	0.5 (3)	C9—C10—C11—C12	−0.6 (2)
C4—C5—C6—C7	0.0 (2)	C15—C10—C11—C12	179.38 (15)
C3—C2—C7—C6	1.6 (2)	C10—C11—C12—C13	−1.4 (2)
C1—C2—C7—C6	−177.07 (14)	C11—C12—C13—C14	1.5 (2)
C5—C6—C7—C2	−1.0 (2)	C10—C9—C14—C13	−2.3 (2)
N2—N1—C8—S2	−170.63 (11)	N2—C9—C14—C13	179.88 (14)
N2—N1—C8—S1	8.92 (19)	C12—C13—C14—C9	0.3 (2)
C1—S1—C8—N1	179.22 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C2–C7 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···S2ⁱ	0.88 (1)	2.50 (1)	3.3625 (14)	169 (2)
N2—H2n···S2ⁱⁱ	0.88 (1)	2.79 (2)	3.5919 (13)	152 (1)
C11—H11···Cg1ⁱⁱⁱ	0.95	2.98	3.8594 (18)	155
C5—H5···Cg2^iv	0.95	2.84	3.7005 (18)	151

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+5/2, y−1/2, −z+3/2; (iv) x−1, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₂S₂
M_r	288.42
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	5.7000 (1), 11.0136 (2), 22.7545 (4)
β (°)	95.198 (2)
V (Å³)	1422.60 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.27
Crystal size (mm)	0.22 × 0.14 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.63, 0.77
No. of measured, independent and observed [I > 2σ(I)] reflections	15011, 2725, 2560
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.097, 1.03
No. of reflections	2725
No. of parameters	179
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)	0.44, −0.23

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 C2–C7 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···S2ⁱ	0.876 (14)	2.498 (14)	3.3625 (14)	169.3 (15)
N2—H2n···S2ⁱⁱ	0.877 (13)	2.794 (16)	3.5919 (13)	151.9 (14)
C11—H11···Cg1ⁱⁱⁱ	0.95	2.98	3.8594 (18)	155
C5—H5···Cg2^iv	0.95	2.84	3.7005 (18)	151

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+5/2, y−1/2, −z+3/2; (iv) x−1, y+1, z.

Footnotes

‡Additional correspondence author, e-mail: kacrouse@gmail.com.

Acknowledgements

Support for the project came from Universiti Putra Malaysia under their Research University Grant Scheme (grant No. 9174000) and from the Malaysian Ministry of Science, Technology and Innovation (grant No. 09–02-04–0752-EA001). 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

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