2,2-Diphenyl-N-(1,3-thia­zol-2-yl)acetamide

Fun, H.-K.; Ooi, C.W.; Nayak, P.S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812013840

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1312-o1313

doi:10.1107/S1600536812013840

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2,2-Diphenyl-N-(1,3-thiazol-2-yl)acetamide

Hoong-Kun Fun,^a ^*‡ Chin Wei Ooi,^a Prakash S. Nayak,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Montepadavu, PO, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 26 March 2012; accepted 30 March 2012; online 6 April 2012)

In the title molecule, C₁₇H₁₄N₂OS, the mean plane of the acetamide group forms dihedral angles of 75.79 (5), 81.85 (6) and 12.32 (5)° with the two phenyl rings and the thiazole ring, respectively. In the crystal, N—H⋯N hydrogen bonds link pairs of molecules into inversion dimers with R₂²(8) ring motifs. The crystal packing is further stabilized by C—H⋯π interactions and by π–π interactions with a centroid–centroid distance of 3.6977 (5) Å.

Related literature

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006 ); Mijin et al. (2008 ). For the coordination abilities of amides, see: Wu et al. (2008 ,2010 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Praveen et al. (2011a ,b ,c ); Fun et al. (2011a ,b ). For standard bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₇H₁₄N₂OS
M_r = 294.36
Monoclinic, P 2₁ /c
a = 5.6915 (1) Å
b = 15.1889 (2) Å
c = 16.5967 (2) Å
β = 97.845 (1)°
V = 1421.32 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 100 K
0.41 × 0.22 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.912, T_max = 0.967
23915 measured reflections
6275 independent reflections
5255 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.106
S = 1.05
6275 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N2ⁱ	0.848 (17)	2.116 (17)	2.9600 (12)	173.0 (17)
C1—H1A⋯Cg2ⁱⁱ	0.95	2.88	3.6647 (11)	141
C12—H12A⋯Cg1ⁱⁱⁱ	0.95	2.92	3.6143 (13)	131
C17—H17A⋯Cg1^iv	0.95	2.61	3.4381 (11)	146
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z; (iii) -x+1, -y+2, -z+1; (iv) -x+2, -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: 10.1107/S1600536812013840/lh5446sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013840/lh5446Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013840/lh5446Isup3.cml

checkCIF report

Comment top

N-Substituted 2-arylacetamides are very interesting compounds because of their structural similarity to the lateral chain of natural benzylpenicillin (Mijin et al., 2006;2008). Amides are also used as ligands due to their excellent coordination abilities (Wu et al., 2008;2010). Crystal structures of some acetamide derivatives viz., N-(4-Chloro-1,3-benzothiazol-2-yl)-2-(3-methylphenyl) acetamide monohydrate, N-(3-Chloro-4-fluorophenyl)-2,2-diphenylacetamide and N-(3-Chloro-4-fluorophenyl)-2-(naphthalen-1-yl)acetamide (Praveen et al., 2011a,b,c) have been reported. In continuation of our work on synthesis of amides (Fun et al., 2011 a, b), we report herein the crystal structure of the title compound (I).

In the title compound (Fig. 1), the mean plane of acetamide (O1/N1/C7/C14) group makes dihedral angles of 75.79 (5)°, 81.85 (6)° and 12.32 (5)° with the two terminal phenyl rings (C1–C6 & C8–C13) and thiazole (S1/N2/C15–C17) ring, respectively. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structure (Praveen et al., 2011a,b,c; Fun et al., 2011a,b).

In the crystal (Fig. 2), intermolecular N1—H1N1···N26ⁱ hydrogen bonds (Table 1) link molecules to form R₂² (8) ring motifs (Bernstein et al., 1995), leading to the formation of dimers. The crystal packing is further stabilized by C—H···π interactions, involving the C1–C6 ring (centroid Cg1) and C8–C13 ring (centroid Cg2). Weak π–π interactions are observed with Cg3···Cg3 = 3.6977 (5) Å [symmetry code: 2-x, 1-y, 1-z], where Cg3 is the centroid of thiazole ring (S1/N2/C15–C17).

Related literature top

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006); Mijin et al. (2008). For the coordination abilities of amides, see: Wu et al. (2008,2010). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Praveen et al. (2011a,b,c); Fun et al. (2011a,b). For standard bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Diphenylacetic acid (0.212 g, 1 mmol), 2-amino thiazole (0.1 g, 1 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) were dissolved in dichloromethane (20 mL). The mixture was stirred in presence of triethylamine at 273 K for about 3 h. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring. The resultant mixture was then extracted three times with dichloromethane. The organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound (I). Single crystals were grown from methylene chloride and methanol (1:1) mixture by the slow evaporation method. (M.P.: 409–411 K).

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.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

2,2-Diphenyl-N-(1,3-thiazol-2-yl)acetamide top

Crystal data top

C₁₇H₁₄N₂OS	F(000) = 616
M_r = 294.36	D_x = 1.376 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9903 reflections
a = 5.6915 (1) Å	θ = 2.5–35.1°
b = 15.1889 (2) Å	µ = 0.23 mm⁻¹
c = 16.5967 (2) Å	T = 100 K
β = 97.845 (1)°	Block, colourless
V = 1421.32 (4) Å³	0.41 × 0.22 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6275 independent reflections
Radiation source: fine-focus sealed tube	5255 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 35.2°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.912, T_max = 0.967	k = −16→24
23915 measured reflections	l = −20→26

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0448P)² + 0.6018P] where P = (F_o² + 2F_c²)/3
6275 reflections	(Δ/σ)_max = 0.002
194 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₇H₁₄N₂OS	V = 1421.32 (4) Å³
M_r = 294.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.6915 (1) Å	µ = 0.23 mm⁻¹
b = 15.1889 (2) Å	T = 100 K
c = 16.5967 (2) Å	0.41 × 0.22 × 0.15 mm
β = 97.845 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6275 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5255 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.967	R_int = 0.026
23915 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.50 e Å⁻³
6275 reflections	Δρ_min = −0.28 e Å⁻³
194 parameters

Special details top

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

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	1.07647 (4)	0.542027 (16)	0.646585 (15)	0.01478 (6)
O1	0.87987 (13)	0.70144 (5)	0.63542 (5)	0.01719 (14)
N1	0.66503 (15)	0.60037 (5)	0.55657 (5)	0.01345 (15)
N2	0.75899 (15)	0.44947 (5)	0.55803 (5)	0.01470 (15)
C1	0.91770 (17)	0.83556 (6)	0.48940 (6)	0.01471 (17)
H1A	0.9756	0.8479	0.5447	0.018*
C2	1.04707 (18)	0.86252 (7)	0.42827 (6)	0.01756 (18)
H2A	1.1911	0.8941	0.4420	0.021*
C3	0.96610 (19)	0.84336 (7)	0.34702 (6)	0.01904 (19)
H3A	1.0555	0.8612	0.3055	0.023*
C4	0.75423 (19)	0.79806 (7)	0.32711 (6)	0.01852 (19)
H4A	0.6989	0.7845	0.2719	0.022*
C5	0.62220 (18)	0.77229 (7)	0.38820 (6)	0.01557 (17)
H5A	0.4761	0.7421	0.3741	0.019*
C6	0.70288 (16)	0.79043 (6)	0.46986 (6)	0.01264 (16)
C7	0.56466 (16)	0.75681 (6)	0.53608 (6)	0.01255 (16)
H7A	0.4160	0.7287	0.5087	0.015*
C8	0.49405 (16)	0.82524 (6)	0.59564 (6)	0.01339 (16)
C9	0.36637 (18)	0.79582 (7)	0.65657 (6)	0.01725 (18)
H9A	0.3371	0.7346	0.6617	0.021*
C10	0.2815 (2)	0.85479 (8)	0.70978 (7)	0.0214 (2)
H10A	0.1937	0.8339	0.7506	0.026*
C11	0.3251 (2)	0.94425 (8)	0.70328 (7)	0.0244 (2)
H11A	0.2682	0.9847	0.7398	0.029*
C12	0.4528 (2)	0.97440 (8)	0.64302 (8)	0.0251 (2)
H12A	0.4833	1.0356	0.6384	0.030*
C13	0.5361 (2)	0.91505 (7)	0.58931 (7)	0.01917 (19)
H13A	0.6222	0.9361	0.5481	0.023*
C14	0.71613 (16)	0.68473 (6)	0.58191 (6)	0.01301 (16)
C15	0.81095 (16)	0.53022 (6)	0.58261 (6)	0.01279 (16)
C16	1.12260 (18)	0.43055 (7)	0.63849 (6)	0.01723 (18)
H16A	1.2576	0.3998	0.6643	0.021*
C17	0.93884 (18)	0.39295 (7)	0.59006 (6)	0.01634 (17)
H17A	0.9337	0.3316	0.5788	0.020*
H1N1	0.548 (3)	0.5890 (11)	0.5207 (10)	0.030 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01364 (10)	0.01391 (11)	0.01602 (11)	0.00093 (7)	−0.00075 (8)	−0.00122 (8)
O1	0.0178 (3)	0.0141 (3)	0.0181 (3)	0.0002 (2)	−0.0030 (3)	−0.0008 (3)
N1	0.0134 (3)	0.0112 (3)	0.0150 (4)	0.0011 (3)	−0.0009 (3)	−0.0007 (3)
N2	0.0149 (3)	0.0119 (3)	0.0168 (4)	0.0012 (3)	0.0004 (3)	−0.0009 (3)
C1	0.0146 (4)	0.0153 (4)	0.0138 (4)	0.0009 (3)	0.0005 (3)	0.0003 (3)
C2	0.0151 (4)	0.0185 (4)	0.0192 (4)	0.0009 (3)	0.0031 (3)	0.0023 (4)
C3	0.0205 (4)	0.0208 (5)	0.0166 (4)	0.0049 (4)	0.0054 (3)	0.0046 (4)
C4	0.0225 (5)	0.0201 (5)	0.0128 (4)	0.0045 (4)	0.0014 (3)	0.0000 (3)
C5	0.0161 (4)	0.0156 (4)	0.0142 (4)	0.0026 (3)	−0.0007 (3)	−0.0015 (3)
C6	0.0134 (4)	0.0118 (4)	0.0127 (4)	0.0024 (3)	0.0014 (3)	0.0003 (3)
C7	0.0126 (4)	0.0114 (4)	0.0133 (4)	0.0008 (3)	0.0008 (3)	−0.0002 (3)
C8	0.0126 (4)	0.0139 (4)	0.0135 (4)	0.0021 (3)	0.0009 (3)	−0.0009 (3)
C9	0.0156 (4)	0.0192 (4)	0.0172 (4)	0.0015 (3)	0.0032 (3)	0.0018 (3)
C10	0.0201 (5)	0.0283 (5)	0.0166 (4)	0.0051 (4)	0.0057 (4)	0.0008 (4)
C11	0.0271 (5)	0.0261 (5)	0.0207 (5)	0.0083 (4)	0.0061 (4)	−0.0047 (4)
C12	0.0321 (6)	0.0159 (5)	0.0289 (6)	0.0043 (4)	0.0101 (5)	−0.0039 (4)
C13	0.0236 (5)	0.0137 (4)	0.0216 (5)	0.0023 (3)	0.0081 (4)	−0.0003 (4)
C14	0.0142 (4)	0.0119 (4)	0.0131 (4)	0.0000 (3)	0.0024 (3)	0.0000 (3)
C15	0.0126 (4)	0.0133 (4)	0.0125 (4)	0.0003 (3)	0.0019 (3)	0.0002 (3)
C16	0.0167 (4)	0.0152 (4)	0.0192 (4)	0.0036 (3)	0.0003 (3)	−0.0002 (3)
C17	0.0166 (4)	0.0129 (4)	0.0193 (4)	0.0031 (3)	0.0013 (3)	−0.0006 (3)

Geometric parameters (Å, º) top

S1—C16	1.7215 (10)	C6—C7	1.5243 (13)
S1—C15	1.7336 (10)	C7—C8	1.5257 (13)
O1—C14	1.2230 (12)	C7—C14	1.5302 (13)
N1—C14	1.3675 (12)	C7—H7A	1.0000
N1—C15	1.3833 (12)	C8—C13	1.3914 (14)
N1—H1N1	0.847 (17)	C8—C9	1.3967 (14)
N2—C15	1.3135 (12)	C9—C10	1.3899 (15)
N2—C17	1.3853 (13)	C9—H9A	0.9500
C1—C2	1.3939 (14)	C10—C11	1.3881 (17)
C1—C6	1.4006 (13)	C10—H10A	0.9500
C1—H1A	0.9500	C11—C12	1.3914 (18)
C2—C3	1.3950 (15)	C11—H11A	0.9500
C2—H2A	0.9500	C12—C13	1.3954 (15)
C3—C4	1.3885 (16)	C12—H12A	0.9500
C3—H3A	0.9500	C13—H13A	0.9500
C4—C5	1.3978 (15)	C16—C17	1.3552 (14)
C4—H4A	0.9500	C16—H16A	0.9500
C5—C6	1.3977 (13)	C17—H17A	0.9500
C5—H5A	0.9500

C16—S1—C15	88.85 (5)	C13—C8—C7	123.77 (9)
C14—N1—C15	122.15 (8)	C9—C8—C7	117.40 (9)
C14—N1—H1N1	121.4 (11)	C10—C9—C8	120.93 (10)
C15—N1—H1N1	116.2 (11)	C10—C9—H9A	119.5
C15—N2—C17	109.65 (8)	C8—C9—H9A	119.5
C2—C1—C6	120.42 (9)	C11—C10—C9	120.01 (10)
C2—C1—H1A	119.8	C11—C10—H10A	120.0
C6—C1—H1A	119.8	C9—C10—H10A	120.0
C1—C2—C3	120.32 (10)	C10—C11—C12	119.63 (10)
C1—C2—H2A	119.8	C10—C11—H11A	120.2
C3—C2—H2A	119.8	C12—C11—H11A	120.2
C4—C3—C2	119.67 (10)	C11—C12—C13	120.18 (11)
C4—C3—H3A	120.2	C11—C12—H12A	119.9
C2—C3—H3A	120.2	C13—C12—H12A	119.9
C3—C4—C5	120.10 (9)	C8—C13—C12	120.55 (10)
C3—C4—H4A	120.0	C8—C13—H13A	119.7
C5—C4—H4A	120.0	C12—C13—H13A	119.7
C6—C5—C4	120.68 (9)	O1—C14—N1	121.79 (9)
C6—C5—H5A	119.7	O1—C14—C7	122.29 (9)
C4—C5—H5A	119.7	N1—C14—C7	115.83 (8)
C5—C6—C1	118.81 (9)	N2—C15—N1	121.47 (9)
C5—C6—C7	119.96 (9)	N2—C15—S1	115.30 (7)
C1—C6—C7	121.14 (8)	N1—C15—S1	123.21 (7)
C6—C7—C8	116.51 (8)	C17—C16—S1	110.32 (7)
C6—C7—C14	106.68 (7)	C17—C16—H16A	124.8
C8—C7—C14	110.22 (8)	S1—C16—H16A	124.8
C6—C7—H7A	107.7	C16—C17—N2	115.87 (9)
C8—C7—H7A	107.7	C16—C17—H17A	122.1
C14—C7—H7A	107.7	N2—C17—H17A	122.1
C13—C8—C9	118.70 (9)

C6—C1—C2—C3	−1.20 (15)	C10—C11—C12—C13	0.13 (19)
C1—C2—C3—C4	0.70 (16)	C9—C8—C13—C12	0.21 (16)
C2—C3—C4—C5	0.39 (16)	C7—C8—C13—C12	175.82 (10)
C3—C4—C5—C6	−1.01 (15)	C11—C12—C13—C8	−0.42 (18)
C4—C5—C6—C1	0.51 (14)	C15—N1—C14—O1	−7.86 (15)
C4—C5—C6—C7	−176.13 (9)	C15—N1—C14—C7	168.96 (8)
C2—C1—C6—C5	0.59 (14)	C6—C7—C14—O1	81.74 (11)
C2—C1—C6—C7	177.19 (9)	C8—C7—C14—O1	−45.64 (12)
C5—C6—C7—C8	−126.30 (9)	C6—C7—C14—N1	−95.07 (9)
C1—C6—C7—C8	57.14 (12)	C8—C7—C14—N1	137.56 (9)
C5—C6—C7—C14	110.15 (9)	C17—N2—C15—N1	177.26 (9)
C1—C6—C7—C14	−66.41 (11)	C17—N2—C15—S1	−0.88 (11)
C6—C7—C8—C13	4.06 (13)	C14—N1—C15—N2	179.68 (9)
C14—C7—C8—C13	125.77 (10)	C14—N1—C15—S1	−2.33 (13)
C6—C7—C8—C9	179.72 (8)	C16—S1—C15—N2	0.84 (8)
C14—C7—C8—C9	−58.57 (11)	C16—S1—C15—N1	−177.26 (9)
C13—C8—C9—C10	0.29 (15)	C15—S1—C16—C17	−0.54 (8)
C7—C8—C9—C10	−175.60 (9)	S1—C16—C17—N2	0.17 (12)
C8—C9—C10—C11	−0.59 (16)	C15—N2—C17—C16	0.44 (13)
C9—C10—C11—C12	0.37 (18)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N2ⁱ	0.848 (17)	2.116 (17)	2.9600 (12)	173.0 (17)
C1—H1A···Cg2ⁱⁱ	0.95	2.88	3.6647 (11)	141
C12—H12A···Cg1ⁱⁱⁱ	0.95	2.92	3.6143 (13)	131
C17—H17A···Cg1^iv	0.95	2.61	3.4381 (11)	146

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₂OS
M_r	294.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.6915 (1), 15.1889 (2), 16.5967 (2)
β (°)	97.845 (1)
V (Å³)	1421.32 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.41 × 0.22 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.912, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	23915, 6275, 5255
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.810

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.106, 1.05
No. of reflections	6275
No. of parameters	194
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.28

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 of the C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N2ⁱ	0.848 (17)	2.116 (17)	2.9600 (12)	173.0 (17)
C1—H1A···Cg2ⁱⁱ	0.9500	2.88	3.6647 (11)	141
C12—H12A···Cg1ⁱⁱⁱ	0.9500	2.92	3.6143 (13)	131
C17—H17A···Cg1^iv	0.9500	2.61	3.4381 (11)	146

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). CWO also thanks the Malaysian Goverment and USM for the award of the post of Research Officer under the Research University Grant No. 1001/PFIZIK/811160. BN thanks the UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP–DRS–Phase 1 programme.

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Volume 68| Part 5| May 2012| Pages o1312-o1313

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