2,2′-Dithio­dianiline: a redetermination at 100 K

Goh, J.H.; Fun, H.-K.; Babu, M.; Kalluraya, B.

doi:10.1107/S1600536810000024

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Pages o292-o293

https://doi.org/10.1107/S1600536810000024

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2,2′-Dithiodianiline: a redetermination at 100 K

Jia Hao Goh,^a ‡ Hoong-Kun Fun,^a ^*§ M. Babu ^b and B. Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 8 December 2009; accepted 1 January 2010; online 9 January 2010)

Structural studies of the title compound [systematic name: 2,2′-(disulfanediyl)dianiline], C₁₂H₁₂N₂S₂, were previously performed at room temperature [Gomes de Mesquita (1967 ). Acta Cryst. 23, 671; Lee & Bryant (1970 ). Acta Cryst. B26, 1729; Ribar et al. (1975 ). Bull. Yugoslav. Crystallogr. Centre, A10, 68]. The results of the current redetermination allow a clarification of the nature of the intra- and intermolecular N—H⋯S hydrogen bonding described in the literature for this compound. On cooling to 100 K, the unit cell contracts most in the c axis, and it changes rather less in the directions involving the strongly hydrogen-bonded chains, which are the a and b axes. In the crystal structure, N—H⋯N hydrogen bonds link neighbouring molecules into two-dimensional frameworks parallel to the ab plane. An additional intermolecular N—H⋯S hydrogen bond has also been established, based on freely refined H-atom positions. Intermolecular C—H⋯π interactions further stabilize the crystal structure.

Related literature

For previously reported structure determinations of the title compound, see: Gomes de Mesquita (1967); Lee & Bryant (1970); Ribar et al. (1975). For general background to and applications of the title compound, see: Garbarczyk et al. (1999 ); Kalluraya et al. (2000 ); Kalluraya & Chimbalkar (2001 ). For a description of the Cambridge Structural Database, see: Allen (2002 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₂H₁₂N₂S₂
M_r = 248.36
Orthorhombic, P b c a
a = 8.2531 (1) Å
b = 13.0278 (2) Å
c = 22.3655 (4) Å
V = 2404.73 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 100 K
0.23 × 0.18 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.912, T_max = 0.934
47724 measured reflections
2750 independent reflections
2417 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.124
S = 1.19
2750 reflections
193 parameters
All H-atom parameters refined
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C7–C12 and C1–C16 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N2ⁱ	0.87 (4)	2.39 (4)	3.222 (3)	160 (4)
N2—H1N2⋯N1ⁱⁱ	0.86 (4)	2.39 (4)	3.184 (3)	155 (3)
N2—H2N2⋯S1ⁱⁱⁱ	0.88 (4)	2.61 (3)	3.436 (2)	156 (3)
C4—H4A⋯Cg1^iv	0.97 (3)	2.95 (3)	3.689 (3)	134 (2)
C9—H9A⋯Cg2^v	0.96 (3)	2.89 (3)	3.637 (3)	135 (2)
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iv) x+1, y, z; (v) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810000024/tk2598sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810000024/tk2598Isup2.hkl

checkCIF report

Comment top

Nitrogen- and sulphur- containing compounds are important intermediates in the synthesis of various heterocyclic compounds. Ortho amino thiophenols are important precursors in the preparation of a variety of heterocycles such as benzothiadiazepines, thiadiazoles, thiadiazines etc. (Kalluraya et al., 2000; Kalluraya & Chimbalkar, 2001). The title compound was obtained during an attempt to study the aerial oxidation of aminothiophenols. Molecular and crystal structures of thioamide derivatives have been analyzed (Garbarczyk et al., 1999).

A search of the November 2008 release of the Cambridge Structural Database (Allen, 2002) reveals that the room temperature crystal structures of the title compound (Fig. 1) were first reported with R = 0.057 for 369 reflections (Gomes de Mesquita, 1967), then followed with R = 0.086 for 1313 reflections (Lee & Bryant, 1970) and R = 0.042 (Ribar et al., 1975). The current redetermination at 100 K increases significantly the precision of the structural and geometrical parameters and provides a lower R value (R = 0.048 based on 2750 independent observed reflections).

Comparison with the previously reported unit cell parameters (Ribar et al., 1975) reveals that on cooling to 100 K, a expands by 0.41 %, whereas b and c contract by 1.15 and 1.74 %, respectively. This can be explained by the fact that along the c axis, the molecules are interconnected by weak C—H···π interactions only whereas along the a and b axes, the molecules are interconnected by the stronger hydrogen bonds (Figs 2 & 3, Table 1). The previously reported structure (Lee & Bryant, 1970) suggests two intramolecular N—H···S hydrogen bonds, but the current work observes no such intramolecular hydrogen bonds with bond angle larger than 120°. The bond lengths are comparable to but more precise than the previously reported structures (Lee & Bryant, 1970; Ribar et al., 1975).

In the crystal structure, molecules are linked into two-dimensional frameworks parallel to the ab plane (Fig. 3) rather than one-dimensional infinite chains as reported previously (Lee & Bryant, 1970). Based on freely refined hydrogen atom positions, an additional intermolecular N2—H2N2···S1 hydrogen bond (Table 1) has also been established. Intermolecular C4—H4A···Cg1 and C9—H9A···Cg2 interactions (Table 1) further stabilize the crystal structure.

Related literature top

For previously reported structure determinations of the title compound, see: Gomes de Mesquita (1967); Lee & Bryant (1970); Ribar et al. (1975). For general background to and applications of the title compound, see: Garbarczyk et al. (1999); Kalluraya et al. (2000); Kalluraya & Chimbalkar (2001). For a description of the Cambridge Structural Database, see: Allen (2002). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound is obtained by exposing 2-aminobenzenethiol to sunlight in an open beaker for two days. The reagent 2-aminobenzenethiol undergoes self aerial oxidation to furnish the crystals. The crude product obtained through the photochemical condition was washed with ethanol and dried. Single crystals suitable for X-ray analysis were obtained from ethanol by slow evaporation.

Structure description top

For previously reported structure determinations of the title compound, see: Gomes de Mesquita (1967); Lee & Bryant (1970); Ribar et al. (1975). For general background to and applications of the title compound, see: Garbarczyk et al. (1999); Kalluraya et al. (2000); Kalluraya & Chimbalkar (2001). For a description of the Cambridge Structural Database, see: Allen (2002). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme.
	Fig. 2. Part of the crystal structure, viewed along the a axis, showing two interlayers being joined along the c axis by weak intermolecular C—H···π interactions. Hydrogen atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.
	Fig. 3. The crystal structure of the title compound, viewed along the c axis, showing a two-dimensional framework parallel to the ab plane. Intermolecular hydrogen bonds are shown as dashed lines.

2,2'-(disulfanediyl)dianiline top

Crystal data top

C₁₂H₁₂N₂S₂	F(000) = 1040
M_r = 248.36	D_x = 1.372 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9179 reflections
a = 8.2531 (1) Å	θ = 3.1–29.9°
b = 13.0278 (2) Å	µ = 0.42 mm⁻¹
c = 22.3655 (4) Å	T = 100 K
V = 2404.73 (6) Å³	Block, yellow
Z = 8	0.23 × 0.18 × 0.17 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2750 independent reflections
Radiation source: fine-focus sealed tube	2417 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.912, T_max = 0.934	k = −16→16
47724 measured reflections	l = −29→29

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	All H-atom parameters refined
S = 1.19	w = 1/[σ²(F_o²) + (0.0383P)² + 5.2113P] where P = (F_o² + 2F_c²)/3
2750 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₂H₁₂N₂S₂	V = 2404.73 (6) Å³
M_r = 248.36	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.2531 (1) Å	µ = 0.42 mm⁻¹
b = 13.0278 (2) Å	T = 100 K
c = 22.3655 (4) Å	0.23 × 0.18 × 0.17 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2750 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2417 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.934	R_int = 0.040
47724 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.124	All H-atom parameters refined
S = 1.19	Δρ_max = 0.50 e Å⁻³
2750 reflections	Δρ_min = −0.43 e Å⁻³
193 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.02244 (8)	0.44246 (5)	0.29158 (3)	0.02175 (17)
S2	−0.18075 (7)	0.49532 (5)	0.33614 (3)	0.01897 (17)
N1	0.1434 (3)	0.65943 (19)	0.27327 (11)	0.0261 (5)
N2	−0.3466 (3)	0.28926 (19)	0.32376 (10)	0.0226 (5)
C1	0.2321 (3)	0.6022 (2)	0.31445 (12)	0.0208 (5)
C2	0.3664 (3)	0.6450 (2)	0.34391 (13)	0.0267 (6)
C3	0.4491 (3)	0.5893 (2)	0.38682 (14)	0.0308 (7)
C4	0.4032 (3)	0.4902 (2)	0.40210 (13)	0.0287 (6)
C5	0.2712 (3)	0.4467 (2)	0.37320 (12)	0.0233 (5)
C6	0.1857 (3)	0.5017 (2)	0.32969 (11)	0.0193 (5)
C7	−0.2077 (3)	0.40351 (19)	0.39331 (11)	0.0171 (5)
C8	−0.1543 (3)	0.4247 (2)	0.45123 (12)	0.0220 (5)
C9	−0.1837 (3)	0.3567 (2)	0.49755 (12)	0.0275 (6)
C10	−0.2661 (4)	0.2664 (2)	0.48554 (13)	0.0295 (6)
C11	−0.3206 (3)	0.2437 (2)	0.42842 (13)	0.0251 (6)
C12	−0.2934 (3)	0.31171 (19)	0.38114 (11)	0.0190 (5)
H2A	0.402 (4)	0.715 (3)	0.3335 (14)	0.034 (9)*
H3A	0.536 (4)	0.621 (3)	0.4078 (15)	0.038 (9)*
H4A	0.457 (4)	0.451 (3)	0.4337 (15)	0.033 (9)*
H5A	0.240 (4)	0.379 (2)	0.3819 (13)	0.025 (8)*
H8A	−0.100 (4)	0.492 (2)	0.4590 (14)	0.027 (8)*
H9A	−0.153 (4)	0.373 (2)	0.5377 (14)	0.022 (8)*
H10A	−0.285 (4)	0.219 (3)	0.5158 (14)	0.030 (9)*
H11A	−0.374 (4)	0.179 (3)	0.4193 (14)	0.029 (8)*
H1N1	0.199 (5)	0.706 (3)	0.2542 (18)	0.048 (11)*
H2N1	0.083 (5)	0.620 (3)	0.2483 (16)	0.040 (10)*
H1N2	−0.422 (5)	0.244 (3)	0.3209 (15)	0.037 (9)*
H2N2	−0.362 (4)	0.343 (3)	0.3004 (14)	0.025 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0167 (3)	0.0245 (3)	0.0240 (3)	−0.0045 (2)	0.0039 (2)	−0.0044 (3)
S2	0.0123 (3)	0.0188 (3)	0.0258 (3)	−0.0004 (2)	0.0000 (2)	0.0029 (2)
N1	0.0241 (12)	0.0220 (12)	0.0321 (13)	0.0011 (10)	0.0068 (10)	0.0039 (10)
N2	0.0204 (11)	0.0205 (11)	0.0268 (12)	−0.0038 (9)	−0.0012 (9)	−0.0006 (9)
C1	0.0160 (12)	0.0212 (12)	0.0253 (12)	0.0025 (10)	0.0079 (10)	−0.0026 (10)
C2	0.0163 (12)	0.0258 (14)	0.0381 (15)	−0.0049 (11)	0.0101 (11)	−0.0089 (12)
C3	0.0112 (12)	0.0430 (17)	0.0382 (16)	−0.0015 (12)	0.0018 (11)	−0.0154 (13)
C4	0.0152 (12)	0.0395 (17)	0.0313 (15)	0.0069 (11)	0.0002 (11)	−0.0045 (13)
C5	0.0185 (12)	0.0235 (13)	0.0278 (13)	0.0035 (10)	0.0050 (10)	−0.0007 (11)
C6	0.0140 (11)	0.0219 (12)	0.0220 (12)	−0.0008 (9)	0.0057 (9)	−0.0013 (10)
C7	0.0100 (11)	0.0188 (12)	0.0225 (12)	0.0029 (9)	0.0026 (9)	0.0022 (9)
C8	0.0144 (12)	0.0275 (14)	0.0242 (13)	0.0028 (10)	−0.0004 (10)	−0.0030 (10)
C9	0.0211 (13)	0.0400 (17)	0.0214 (13)	0.0066 (12)	0.0004 (10)	0.0007 (12)
C10	0.0278 (14)	0.0325 (16)	0.0282 (14)	0.0090 (12)	0.0086 (12)	0.0095 (12)
C11	0.0214 (13)	0.0206 (13)	0.0333 (14)	0.0022 (11)	0.0068 (11)	0.0029 (11)
C12	0.0114 (11)	0.0212 (12)	0.0244 (12)	0.0028 (9)	0.0038 (9)	−0.0009 (10)

Geometric parameters (Å, º) top

S1—C6	1.771 (3)	C4—C5	1.388 (4)
S1—S2	2.0687 (9)	C4—H4A	0.97 (3)
S2—C7	1.765 (3)	C5—C6	1.400 (4)
N1—C1	1.392 (4)	C5—H5A	0.94 (3)
N1—H1N1	0.87 (4)	C7—C8	1.396 (4)
N1—H2N1	0.91 (4)	C7—C12	1.416 (3)
N2—C12	1.388 (3)	C8—C9	1.384 (4)
N2—H1N2	0.86 (4)	C8—H8A	1.00 (3)
N2—H2N2	0.88 (3)	C9—C10	1.386 (4)
C1—C2	1.405 (4)	C9—H9A	0.96 (3)
C1—C6	1.407 (4)	C10—C11	1.386 (4)
C2—C3	1.383 (4)	C10—H10A	0.93 (3)
C2—H2A	0.98 (3)	C11—C12	1.397 (4)
C3—C4	1.388 (4)	C11—H11A	0.97 (3)
C3—H3A	0.95 (4)

C6—S1—S2	103.87 (9)	C6—C5—H5A	119 (2)
C7—S2—S1	103.05 (8)	C5—C6—C1	120.5 (2)
C1—N1—H1N1	115 (3)	C5—C6—S1	119.7 (2)
C1—N1—H2N1	113 (2)	C1—C6—S1	119.8 (2)
H1N1—N1—H2N1	112 (3)	C8—C7—C12	120.2 (2)
C12—N2—H1N2	116 (2)	C8—C7—S2	119.9 (2)
C12—N2—H2N2	115 (2)	C12—C7—S2	119.74 (19)
H1N2—N2—H2N2	113 (3)	C9—C8—C7	120.9 (3)
N1—C1—C2	120.8 (3)	C9—C8—H8A	120.6 (18)
N1—C1—C6	121.0 (2)	C7—C8—H8A	118.4 (18)
C2—C1—C6	118.1 (3)	C8—C9—C10	119.0 (3)
C3—C2—C1	120.4 (3)	C8—C9—H9A	121.3 (18)
C3—C2—H2A	120 (2)	C10—C9—H9A	119.7 (18)
C1—C2—H2A	119 (2)	C9—C10—C11	121.2 (3)
C2—C3—C4	121.6 (3)	C9—C10—H10A	121 (2)
C2—C3—H3A	119 (2)	C11—C10—H10A	118 (2)
C4—C3—H3A	119 (2)	C10—C11—C12	120.7 (3)
C5—C4—C3	118.7 (3)	C10—C11—H11A	121.7 (19)
C5—C4—H4A	119 (2)	C12—C11—H11A	117.6 (19)
C3—C4—H4A	122 (2)	N2—C12—C11	121.0 (2)
C4—C5—C6	120.7 (3)	N2—C12—C7	120.9 (2)
C4—C5—H5A	120 (2)	C11—C12—C7	118.0 (2)

C6—S1—S2—C7	−89.29 (13)	S1—S2—C7—C8	99.8 (2)
N1—C1—C2—C3	176.9 (2)	S1—S2—C7—C12	−84.50 (19)
C6—C1—C2—C3	−0.4 (4)	C12—C7—C8—C9	0.1 (4)
C1—C2—C3—C4	0.1 (4)	S2—C7—C8—C9	175.7 (2)
C2—C3—C4—C5	0.2 (4)	C7—C8—C9—C10	0.6 (4)
C3—C4—C5—C6	−0.3 (4)	C8—C9—C10—C11	−0.7 (4)
C4—C5—C6—C1	0.0 (4)	C9—C10—C11—C12	0.1 (4)
C4—C5—C6—S1	177.7 (2)	C10—C11—C12—N2	179.6 (3)
N1—C1—C6—C5	−177.0 (2)	C10—C11—C12—C7	0.5 (4)
C2—C1—C6—C5	0.3 (4)	C8—C7—C12—N2	−179.7 (2)
N1—C1—C6—S1	5.4 (3)	S2—C7—C12—N2	4.7 (3)
C2—C1—C6—S1	−177.36 (19)	C8—C7—C12—C11	−0.6 (3)
S2—S1—C6—C5	98.6 (2)	S2—C7—C12—C11	−176.27 (19)
S2—S1—C6—C1	−83.8 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids for C7–C12 and C1–C16 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N2ⁱ	0.87 (4)	2.39 (4)	3.222 (3)	160 (4)
N2—H1N2···N1ⁱⁱ	0.86 (4)	2.39 (4)	3.184 (3)	155 (3)
N2—H2N2···S1ⁱⁱⁱ	0.88 (4)	2.61 (3)	3.436 (2)	156 (3)
C4—H4A···Cg1^iv	0.97 (3)	2.95 (3)	3.689 (3)	134 (2)
C9—H9A···Cg2^v	0.96 (3)	2.89 (3)	3.637 (3)	135 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂N₂S₂
M_r	248.36
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	8.2531 (1), 13.0278 (2), 22.3655 (4)
V (Å³)	2404.73 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.23 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.912, 0.934
No. of measured, independent and observed [I > 2σ(I)] reflections	47724, 2750, 2417
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.124, 1.19
No. of reflections	2750
No. of parameters	193
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.43

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids for C7–C12 and C1–C16 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N2ⁱ	0.87 (4)	2.39 (4)	3.222 (3)	160 (4)
N2—H1N2···N1ⁱⁱ	0.86 (4)	2.39 (4)	3.184 (3)	155 (3)
N2—H2N2···S1ⁱⁱⁱ	0.88 (4)	2.61 (3)	3.436 (2)	156 (3)
C4—H4A···Cg1^iv	0.97 (3)	2.95 (3)	3.689 (3)	134 (2)
C9—H9A···Cg2^v	0.96 (3)	2.89 (3)	3.637 (3)	135 (2)

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

Footnotes

‡Thomson Reuters ResearcherID: C-7576-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

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