1-Benzoyl-3,3-dibutyl­thio­urea

Gunasekaran, N.; Karvembu, R.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536810037177

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2601

doi:10.1107/S1600536810037177

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1-Benzoyl-3,3-dibutylthiourea

N. Gunasekaran,^a R. Karvembu,^a ‡ Seik Weng Ng ^b and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 13 September 2010; accepted 16 September 2010; online 25 September 2010)

The title molecule, C₁₆H₂₄N₂OS, is twisted about the central N(H)—C bond with a C—N(H)—C—N torsion angle of −62.67 (15)°. The carbonyl group is twisted out of the plane of the benzene ring, forming a C—C—C=O torsion angle of −25.06 (17)°. In the crystal, molecules related by centres of symmetry are linked by pairs of intermolecular N—H⋯S hydrogen bonds, forming eight-membered {⋯HNCS}₂ synthons. These are further connected by weak via C—H⋯O contacts, forming a two-dimensional array in the bc plane.

Related literature

For pharmaceutical applications of thiourea derivatives, see: Binzet et al. (2009 ); Lipowska et al. (1996 ). For the coordination potential of thiourea derivatives, see: Henderson et al. (2002 ); Hallale et al. (2005 ). For the use of ruthenium(III) complexes of thioureas as catalysts, see: Gunasekaran & Karvembu (2010 ). For related structures, see: Gunasekaran et al. (2010a ,b ).

Experimental

Crystal data

C₁₆H₂₄N₂OS
M_r = 292.43
Monoclinic, P 2₁ /c
a = 10.3213 (7) Å
b = 15.7043 (11) Å
c = 10.0992 (7) Å
β = 98.751 (1)°
V = 1617.91 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 100 K
0.40 × 0.40 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.925, T_max = 0.971
15120 measured reflections
3725 independent reflections
3204 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.092
S = 1.03
3725 reflections
185 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯S1ⁱ	0.85 (1)	2.64 (1)	3.4547 (11)	160 (1)
C2—H2a⋯O1ⁱⁱ	0.95	2.47	3.4102 (16)	173
C14—H14b⋯O1ⁱⁱⁱ	0.99	2.58	3.3559 (16)	136
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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/S1600536810037177/lh5132sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037177/lh5132Isup2.hkl

checkCIF report

Comment top

Thiourea and its derivatives have important pharmaceutical applications (Binzet et al., 2009; Lipowska et al., 1996). These species are also considered as versatile and attractive ligands due to their coordination ability to a wide range of metal centres, either as neutral ligands, or as mono- or di-anions (Henderson et al., 2002; Hallale et al., 2005). Their coordination complexes can also exhibit useful properties. As an example of a recent application, ruthenium(III) complexes containing these ligands have recently been used as catalysts for oxidation of alcohols to carbonyl compounds (Gunasekaran & Karvembu, 2010). In continuation of structural studies of these molecules (Gunasekaran et al., 2010a; Gunasekaran et al., 2010b), (I), the crystal structure of the title compound was carried out.

In (I), the molecule is twisted about the central N1—C8 bond as reflected in the value of the C7—N1—C8—S1 torsion angle of 119.81 (11) ° and C7—N1—C8—-N2 of -62.67 (15) ° (see Fig. 1). The carbonyl group is twisted out of the plane of the benzene ring to which it is attached [the C2—C1—C7—O1 dihedral angle = -25.06 (17) °], and the butyl groups lie on opposite sides of the mean plane formed by the N₂S atoms.

The most prominent intermolecular interactions are of the type N—H···S, occurring between centrosymmetrically related molecules to form an eight-membered {···HNCS}₂ synthon, Table 1. The dimeric aggregates are linked into a 2-D array via C—H···O contacts, Fig. 2 and Table 1. The layers thus formed stack along the a axis, Fig. 3.

Related literature top

For pharmaceutical applications of thiourea derivatives, see: Binzet et al. (2009); Lipowska et al. (1996). For the coordination potential of thiourea derivatives, see: Henderson et al. (2002); Hallale et al. (2005). For the use of ruthenium(III) complexes of thioureas as catalysts, see: Gunasekaran & Karvembu (2010). For related structures, see: Gunasekaran et al. (2010a,b).

Experimental top

A solution of benzoyl chloride (0.7029 g, 5 mmol) in acetone (50 ml) was added drop wise to a suspension of potassium thiocyanate (0.4859 g, 5 mmol) in anhydrous acetone (50 ml). The reaction mixture was heated under reflux for 45 min and then cooled to room temperature. A solution of dibutyl amine (0.6462 g, 5 mmol) in acetone (30 ml) was added and the resulting mixture was stirred for 2 h. Hydrochloric acid (0.1 N, 300 ml) was added and the resulting white solid was filtered, washed with water and dried in vacuo. Single crystals of (I) for X-ray diffraction were grown at room temperature from its acetone solution. M. pt. 358–360 K; Yield 76%. FT—IR (KBr) ν(N—H) 3174, ν(C═O) 1688, ν(C═S) 1243 cm^-1.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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. View of the 2-D array in (I). The N–H···S hydrogen bonding and C–H···O contacts are shown as orange and blue dashed lines, respectively.
	Fig. 3. Unit-cell contents shown in projection down the a axis in (I) showing the stacking of layers. The N–H···S hydrogen bonding and C–H···O contacts are shown as orange and blue dashed lines, respectively.

1-Benzoyl-3,3-dibutylthiourea top

Crystal data top

C₁₆H₂₄N₂OS	F(000) = 632
M_r = 292.43	D_x = 1.201 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5696 reflections
a = 10.3213 (7) Å	θ = 4.4–28.3°
b = 15.7043 (11) Å	µ = 0.20 mm⁻¹
c = 10.0992 (7) Å	T = 100 K
β = 98.751 (1)°	Block, colourless
V = 1617.91 (19) Å³	0.40 × 0.40 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3725 independent reflections
Radiation source: fine-focus sealed tube	3204 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
T_min = 0.925, T_max = 0.971	k = −20→20
15120 measured reflections	l = −13→12

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0441P)² + 0.602P] where P = (F_o² + 2F_c²)/3
3725 reflections	(Δ/σ)_max = 0.001
185 parameters	Δρ_max = 0.31 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₆H₂₄N₂OS	V = 1617.91 (19) Å³
M_r = 292.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.3213 (7) Å	µ = 0.20 mm⁻¹
b = 15.7043 (11) Å	T = 100 K
c = 10.0992 (7) Å	0.40 × 0.40 × 0.15 mm
β = 98.751 (1)°

Data collection top

Bruker SMART APEX diffractometer	3725 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3204 reflections with I > 2σ(I)
T_min = 0.925, T_max = 0.971	R_int = 0.036
15120 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	1 restraint
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.31 e Å⁻³
3725 reflections	Δρ_min = −0.26 e Å⁻³
185 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	0.31557 (3)	0.56922 (2)	0.46025 (3)	0.01948 (10)
O1	0.49254 (9)	0.58166 (6)	0.12400 (9)	0.0197 (2)
N1	0.53208 (10)	0.59664 (7)	0.35231 (10)	0.0161 (2)
H1n	0.5663 (15)	0.5638 (9)	0.4155 (13)	0.027 (4)*
N2	0.36726 (10)	0.69784 (7)	0.30300 (10)	0.0178 (2)
C1	0.70516 (12)	0.54489 (8)	0.23442 (12)	0.0169 (2)
C2	0.73420 (13)	0.49345 (8)	0.13018 (13)	0.0214 (3)
H2A	0.6667	0.4767	0.0604	0.026*
C3	0.86217 (14)	0.46701 (9)	0.12914 (15)	0.0275 (3)
H3A	0.8821	0.4311	0.0592	0.033*
C4	0.96133 (14)	0.49266 (9)	0.22958 (15)	0.0281 (3)
H4A	1.0489	0.4746	0.2278	0.034*
C5	0.93326 (13)	0.54464 (9)	0.33254 (14)	0.0252 (3)
H5A	1.0014	0.5624	0.4010	0.030*
C6	0.80499 (13)	0.57064 (8)	0.33523 (13)	0.0205 (3)
H6A	0.7853	0.6060	0.4059	0.025*
C7	0.56729 (12)	0.57488 (7)	0.22861 (12)	0.0159 (2)
C8	0.40510 (12)	0.62549 (8)	0.36472 (12)	0.0164 (2)
C9	0.23215 (13)	0.72865 (8)	0.29594 (13)	0.0205 (3)
H9A	0.2320	0.7916	0.2996	0.025*
H9B	0.1944	0.7070	0.3739	0.025*
C10	0.14839 (12)	0.69899 (8)	0.16698 (13)	0.0202 (3)
H10A	0.1403	0.6362	0.1687	0.024*
H10B	0.1926	0.7144	0.0899	0.024*
C11	0.01211 (14)	0.73842 (9)	0.14782 (14)	0.0274 (3)
H11A	−0.0298	0.7261	0.2276	0.033*
H11B	0.0202	0.8010	0.1407	0.033*
C12	−0.07515 (14)	0.70524 (10)	0.02386 (14)	0.0282 (3)
H12A	−0.1617	0.7321	0.0166	0.042*
H12B	−0.0845	0.6434	0.0308	0.042*
H12C	−0.0356	0.7189	−0.0558	0.042*
C13	0.45409 (13)	0.75523 (8)	0.24042 (12)	0.0194 (3)
H13A	0.4005	0.7903	0.1711	0.023*
H13B	0.5153	0.7208	0.1959	0.023*
C14	0.53205 (13)	0.81332 (8)	0.34351 (13)	0.0218 (3)
H14A	0.5934	0.7786	0.4065	0.026*
H14B	0.4713	0.8425	0.3956	0.026*
C15	0.60954 (14)	0.87993 (8)	0.27769 (14)	0.0247 (3)
H15A	0.5473	0.9163	0.2184	0.030*
H15B	0.6574	0.9168	0.3483	0.030*
C16	0.70717 (14)	0.84140 (9)	0.19606 (14)	0.0265 (3)
H16A	0.7538	0.8871	0.1570	0.040*
H16B	0.6603	0.8061	0.1242	0.040*
H16C	0.7703	0.8062	0.2544	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01575 (16)	0.02258 (17)	0.02072 (17)	0.00138 (11)	0.00475 (12)	0.00432 (12)
O1	0.0204 (5)	0.0224 (4)	0.0150 (4)	−0.0002 (3)	−0.0014 (4)	−0.0001 (3)
N1	0.0144 (5)	0.0204 (5)	0.0133 (5)	0.0021 (4)	0.0010 (4)	0.0027 (4)
N2	0.0170 (5)	0.0197 (5)	0.0162 (5)	0.0014 (4)	0.0007 (4)	0.0015 (4)
C1	0.0165 (6)	0.0178 (6)	0.0169 (6)	−0.0016 (4)	0.0042 (5)	0.0036 (4)
C2	0.0238 (7)	0.0202 (6)	0.0207 (6)	−0.0016 (5)	0.0048 (5)	0.0000 (5)
C3	0.0292 (8)	0.0245 (7)	0.0310 (8)	0.0039 (6)	0.0121 (6)	−0.0009 (6)
C4	0.0199 (7)	0.0292 (7)	0.0372 (8)	0.0061 (5)	0.0102 (6)	0.0093 (6)
C5	0.0179 (7)	0.0312 (7)	0.0258 (7)	−0.0025 (5)	0.0010 (5)	0.0064 (6)
C6	0.0191 (6)	0.0247 (6)	0.0178 (6)	−0.0020 (5)	0.0038 (5)	0.0020 (5)
C7	0.0174 (6)	0.0143 (5)	0.0160 (6)	−0.0028 (4)	0.0026 (5)	0.0009 (4)
C8	0.0146 (6)	0.0199 (6)	0.0140 (6)	0.0005 (4)	−0.0001 (4)	−0.0013 (4)
C9	0.0199 (6)	0.0220 (6)	0.0191 (6)	0.0066 (5)	0.0015 (5)	0.0000 (5)
C10	0.0190 (6)	0.0241 (6)	0.0171 (6)	0.0036 (5)	0.0016 (5)	0.0003 (5)
C11	0.0239 (7)	0.0314 (7)	0.0248 (7)	0.0096 (6)	−0.0025 (5)	−0.0028 (6)
C12	0.0210 (7)	0.0386 (8)	0.0238 (7)	0.0056 (6)	−0.0008 (5)	0.0007 (6)
C13	0.0229 (6)	0.0174 (6)	0.0176 (6)	−0.0008 (5)	0.0019 (5)	0.0023 (5)
C14	0.0217 (7)	0.0247 (6)	0.0190 (6)	0.0007 (5)	0.0028 (5)	−0.0045 (5)
C15	0.0270 (7)	0.0216 (6)	0.0247 (7)	−0.0026 (5)	0.0013 (5)	−0.0051 (5)
C16	0.0227 (7)	0.0313 (7)	0.0253 (7)	−0.0010 (6)	0.0029 (6)	0.0025 (6)

Geometric parameters (Å, º) top

S1—C8	1.6843 (13)	C9—H9B	0.9900
O1—C7	1.2144 (15)	C10—C11	1.5221 (18)
N1—C7	1.3955 (16)	C10—H10A	0.9900
N1—C8	1.4102 (16)	C10—H10B	0.9900
N1—H1n	0.854 (9)	C11—C12	1.5188 (19)
N2—C8	1.3259 (16)	C11—H11A	0.9900
N2—C9	1.4675 (16)	C11—H11B	0.9900
N2—C13	1.4790 (16)	C12—H12A	0.9800
C1—C6	1.3938 (18)	C12—H12B	0.9800
C1—C2	1.3953 (18)	C12—H12C	0.9800
C1—C7	1.4915 (17)	C13—C14	1.5194 (17)
C2—C3	1.3861 (19)	C13—H13A	0.9900
C2—H2A	0.9500	C13—H13B	0.9900
C3—C4	1.387 (2)	C14—C15	1.5289 (19)
C3—H3A	0.9500	C14—H14A	0.9900
C4—C5	1.387 (2)	C14—H14B	0.9900
C4—H4A	0.9500	C15—C16	1.5212 (19)
C5—C6	1.3896 (19)	C15—H15A	0.9900
C5—H5A	0.9500	C15—H15B	0.9900
C6—H6A	0.9500	C16—H16A	0.9800
C9—C10	1.5225 (18)	C16—H16B	0.9800
C9—H9A	0.9900	C16—H16C	0.9800

C7—N1—C8	122.03 (10)	C9—C10—H10B	109.2
C7—N1—H1n	112.7 (11)	C11—C10—H10B	109.2
C8—N1—H1n	114.3 (11)	H10A—C10—H10B	107.9
C8—N2—C9	121.01 (11)	C12—C11—C10	112.69 (12)
C8—N2—C13	124.66 (11)	C12—C11—H11A	109.1
C9—N2—C13	114.30 (10)	C10—C11—H11A	109.1
C6—C1—C2	119.95 (12)	C12—C11—H11B	109.1
C6—C1—C7	122.14 (11)	C10—C11—H11B	109.1
C2—C1—C7	117.80 (11)	H11A—C11—H11B	107.8
C3—C2—C1	119.57 (13)	C11—C12—H12A	109.5
C3—C2—H2A	120.2	C11—C12—H12B	109.5
C1—C2—H2A	120.2	H12A—C12—H12B	109.5
C4—C3—C2	120.37 (13)	C11—C12—H12C	109.5
C4—C3—H3A	119.8	H12A—C12—H12C	109.5
C2—C3—H3A	119.8	H12B—C12—H12C	109.5
C3—C4—C5	120.29 (13)	N2—C13—C14	111.42 (10)
C3—C4—H4A	119.9	N2—C13—H13A	109.3
C5—C4—H4A	119.9	C14—C13—H13A	109.3
C4—C5—C6	119.73 (13)	N2—C13—H13B	109.3
C4—C5—H5A	120.1	C14—C13—H13B	109.3
C6—C5—H5A	120.1	H13A—C13—H13B	108.0
C5—C6—C1	120.08 (13)	C13—C14—C15	111.74 (11)
C5—C6—H6A	120.0	C13—C14—H14A	109.3
C1—C6—H6A	120.0	C15—C14—H14A	109.3
O1—C7—N1	122.67 (11)	C13—C14—H14B	109.3
O1—C7—C1	122.54 (11)	C15—C14—H14B	109.3
N1—C7—C1	114.77 (10)	H14A—C14—H14B	107.9
N2—C8—N1	116.41 (11)	C16—C15—C14	113.39 (11)
N2—C8—S1	124.81 (10)	C16—C15—H15A	108.9
N1—C8—S1	118.73 (9)	C14—C15—H15A	108.9
N2—C9—C10	110.64 (10)	C16—C15—H15B	108.9
N2—C9—H9A	109.5	C14—C15—H15B	108.9
C10—C9—H9A	109.5	H15A—C15—H15B	107.7
N2—C9—H9B	109.5	C15—C16—H16A	109.5
C10—C9—H9B	109.5	C15—C16—H16B	109.5
H9A—C9—H9B	108.1	H16A—C16—H16B	109.5
C9—C10—C11	112.19 (11)	C15—C16—H16C	109.5
C9—C10—H10A	109.2	H16A—C16—H16C	109.5
C11—C10—H10A	109.2	H16B—C16—H16C	109.5

C6—C1—C2—C3	1.20 (19)	C9—N2—C8—N1	172.80 (10)
C7—C1—C2—C3	177.48 (11)	C13—N2—C8—N1	−9.26 (17)
C1—C2—C3—C4	−1.2 (2)	C9—N2—C8—S1	−9.85 (17)
C2—C3—C4—C5	0.4 (2)	C13—N2—C8—S1	168.09 (9)
C3—C4—C5—C6	0.4 (2)	C7—N1—C8—N2	−62.67 (15)
C4—C5—C6—C1	−0.3 (2)	C7—N1—C8—S1	119.81 (11)
C2—C1—C6—C5	−0.46 (19)	C8—N2—C9—C10	−93.34 (14)
C7—C1—C6—C5	−176.57 (12)	C13—N2—C9—C10	88.52 (13)
C8—N1—C7—O1	2.17 (18)	N2—C9—C10—C11	−173.07 (11)
C8—N1—C7—C1	−179.45 (11)	C9—C10—C11—C12	−176.53 (12)
C6—C1—C7—O1	151.14 (12)	C8—N2—C13—C14	−82.29 (15)
C2—C1—C7—O1	−25.06 (17)	C9—N2—C13—C14	95.77 (12)
C6—C1—C7—N1	−27.25 (16)	N2—C13—C14—C15	−173.16 (10)
C2—C1—C7—N1	156.56 (11)	C13—C14—C15—C16	−59.57 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···S1ⁱ	0.85 (1)	2.64 (1)	3.4547 (11)	160 (1)
C2—H2a···O1ⁱⁱ	0.95	2.47	3.4102 (16)	173
C14—H14b···O1ⁱⁱⁱ	0.99	2.58	3.3559 (16)	136

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

Experimental details

Crystal data
Chemical formula	C₁₆H₂₄N₂OS
M_r	292.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.3213 (7), 15.7043 (11), 10.0992 (7)
β (°)	98.751 (1)
V (Å³)	1617.91 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.40 × 0.40 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.925, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	15120, 3725, 3204
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.03
No. of reflections	3725
No. of parameters	185
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.26

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···S1ⁱ	0.854 (9)	2.638 (10)	3.4547 (11)	160.4 (14)
C2—H2a···O1ⁱⁱ	0.95	2.47	3.4102 (16)	173
C14—H14b···O1ⁱⁱⁱ	0.99	2.58	3.3559 (16)	136

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

Footnotes

‡Additional correspondence author, e-mail: kar@nitt.edu.

Acknowledgements

NG thanks the NITT for a Fellowship. The authors also thank the University of Malaya for support of the crystallographic facility.

References

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