N-(Biphenyl-4-ylcarbon­yl)-N′-(2-pyridylmeth­yl)thio­urea

Yamin, B.M.; Deris, H.; Malik, Z.M.; Yousuf, S.

doi:10.1107/S1600536807067499

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o360

doi:10.1107/S1600536807067499

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N-(Biphenyl-4-ylcarbonyl)-N′-(2-pyridylmethyl)thiourea

Bohari M. Yamin,^a Hidayah Deris,^a Zaw Myint Malik ^a and Sammer Yousuf ^b ^*

^aSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, UKM 43600 Bangi Selangor, Malaysia, and ^bHEJ Research Institute of Chemistry, University of Karachi, Karachi 75270, Pakistan
^*Correspondence e-mail: sammer_yousuf@yahoo.com

(Received 29 November 2007; accepted 18 December 2007; online 4 January 2008)

In the title compound, C₂₀H₁₇N₃OS, the dihedral angle between the benzene rings of the biphenyl fragment is 36.84 (9)°. The trans–cis geometry of the thiourea unit is stabilized by intramolecular N—H⋯O and N—H⋯N hydrogen bonds between the H atom of the cis thioamide and the carbonyl O and pyridine N atoms, respectively. In the crystal structure, intermolecular N—H⋯S hydrogen bonds form centrosymmetric dimers extending along the b axis.

Related literature

For the crystal structure of the biphenyl-4-carbonylthiourea analogue, see: Arif & Yamin (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₁₇N₃OS
M_r = 347.43
Triclinic, $[P \overline 1]$
a = 7.467 (2) Å
b = 9.364 (2) Å
c = 13.184 (3) Å
α = 101.529 (5)°
β = 99.113 (4)°
γ = 101.543 (5)°
V = 865.9 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 273 (2) K
0.45 × 0.37 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.915, T_max = 0.965
8243 measured reflections
3036 independent reflections
2561 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.101
S = 1.05
3036 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.99	2.6681 (19)	135
N2—H2⋯N3	0.86	2.24	2.6488 (19)	109
N1—H1⋯S1ⁱ	0.86	2.79	3.4759 (17)	138
Symmetry code: (i) -x, -y+2, -z+2.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067499/at2519sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807067499/at2519Isup2.hkl

checkCIF report

Comment top

The title compound, (I), analogous to N-(biphenyl-4-carbonyl)-N'- (2-chlorophenyl)thiourea (II) (Arif & Yamin, 2007) except the 2-chlorobenzene group is replaced by the 2-methyl-pyridine group (Fig.1). The molecule maintains its trans-cis configuration with respect to the position of the biphenyl-4-carbonyl and 2-methyl-pyridin groups relative the thiono sulfur atom across the C14—N1 and C14—N2 bonds, respectively. Other bond lengths and angles are in normal ranges (Allen et al., 1987) and comparable to those in (II). However, the dihedral angle between the benzene rings of the biphenyl fragment, (C1—C6) and (C7—C12) of 36,84 (9)° is larger than that (20.71 (17)°) in (II). Both the central C13/O1/N1/C14/S1/N2/C15 fragment and pyridine ring (N3/C16—C20), are planar with a maximum deviation of 0.032 (2)Å for atom N1 atom from the least square plane of the central fragment. The central fragment makes dihedral angles with the (C7—C12) benzene and (N3/C16—C20) pyridine rings of 16.39 (8) and 13.21 (6)°, respectively. The trans-cis geometry of the thiourea moiety is stabilized by the relatively strong N2—H2···O1 and a weak N2—H2···N3 intramolecular hydrogen bonds (Table 2). In the crystal structure, the molecules are linked by N1—H1···S1 intermolecular hydrogen bonds to form centrosymmetric dimers and are arranged parallel to b axis (Fig.2). In (II), the molecule is stabilized by van der Waal and π-π interactions.

Related literature top

For the crystal structure of the biphenyl-4-carbonylthiourea analogue, see: (Arif & Yamin, 2007). For bond-length data, see: Allen et al. (1987).

Experimental top

The mixrure of biphenyl 1–4 carbonyl chloride (5.417 g, 0.025 mol), with the equimolar amount of ammonium thiocyanate (1.903 g, 0.025 mol) and 2-picolylamine (2.704 g, 0.025 mol) in 30 ml dry acetone was refluxed with stirring for 4 h. The solution was filtered and left to evaporate at room temperature. The black precipitate obtained after a few days, was washed with water and cold ethanol (80%; m.p 416.4–419.2 K). Suitable crystals for X-ray investigation were obtained byrecrystallization from mixture of dichloromethane and n-Hexane (1:3 v/v).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsods are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I) viewed down the a axis. Hydrogen bonds are shown by dashed lines.

N-(Biphenyl-4-ylcarbonyl)-N'-(2-pyridylmethyl)thiourea top

Crystal data top

C₂₀H₁₇N₃OS	Z = 2
M_r = 347.43	F(000) = 364
Triclinic, P1	D_x = 1.333 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.467 (2) Å	Cell parameters from 3740 reflections
b = 9.364 (2) Å	θ = 1.6–25.0°
c = 13.184 (3) Å	µ = 0.20 mm⁻¹
α = 101.529 (5)°	T = 273 K
β = 99.113 (4)°	Block, colourless
γ = 101.543 (5)°	0.45 × 0.37 × 0.18 mm
V = 865.9 (4) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3036 independent reflections
Radiation source: fine-focus sealed tube	2561 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.0°, θ_min = 1.6°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −11→11
T_min = 0.915, T_max = 0.965	l = −15→15
8243 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0535P)² + 0.1413P] where P = (F_o² + 2F_c²)/3
3036 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₀H₁₇N₃OS	γ = 101.543 (5)°
M_r = 347.43	V = 865.9 (4) Å³
Triclinic, P1	Z = 2
a = 7.467 (2) Å	Mo Kα radiation
b = 9.364 (2) Å	µ = 0.20 mm⁻¹
c = 13.184 (3) Å	T = 273 K
α = 101.529 (5)°	0.45 × 0.37 × 0.18 mm
β = 99.113 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3036 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2561 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.965	R_int = 0.019
8243 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.05	Δρ_max = 0.20 e Å⁻³
3036 reflections	Δρ_min = −0.19 e Å⁻³
226 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	0.04886 (8)	0.78345 (5)	1.01142 (3)	0.06855 (19)
O1	0.0915 (2)	0.84641 (13)	0.68251 (9)	0.0672 (4)
N1	0.1098 (2)	0.91996 (14)	0.85943 (10)	0.0523 (4)
H1	0.1330	0.9985	0.9106	0.063*
N2	0.00553 (19)	0.66245 (13)	0.80744 (10)	0.0481 (3)
H2	0.0145	0.6723	0.7448	0.058*
N3	−0.09400 (19)	0.44728 (14)	0.63072 (10)	0.0488 (3)
C1	0.3283 (3)	1.20743 (18)	0.85384 (13)	0.0578 (4)
H1A	0.3503	1.1786	0.9173	0.069*
C2	0.4042 (3)	1.35237 (19)	0.84981 (13)	0.0570 (4)
H2A	0.4774	1.4198	0.9109	0.068*
C3	0.3741 (2)	1.40021 (17)	0.75677 (12)	0.0477 (4)
C4	0.2679 (2)	1.29480 (18)	0.66663 (13)	0.0500 (4)
H4	0.2473	1.3231	0.6029	0.060*
C5	0.1927 (2)	1.14970 (18)	0.66996 (12)	0.0497 (4)
H5	0.1232	1.0811	0.6084	0.060*
C6	0.2193 (2)	1.10431 (17)	0.76401 (12)	0.0476 (4)
C7	0.4562 (2)	1.55747 (18)	0.75548 (13)	0.0515 (4)
C8	0.4688 (3)	1.6749 (2)	0.84207 (15)	0.0643 (5)
H8	0.4199	1.6550	0.8998	0.077*
C9	0.5536 (3)	1.8209 (2)	0.84273 (18)	0.0762 (6)
H9	0.5616	1.8986	0.9009	0.091*
C10	0.6255 (3)	1.8512 (2)	0.7583 (2)	0.0830 (7)
H10	0.6842	1.9491	0.7595	0.100*
C11	0.6113 (3)	1.7377 (2)	0.67184 (19)	0.0781 (6)
H11	0.6591	1.7591	0.6141	0.094*
C12	0.5262 (2)	1.5910 (2)	0.66975 (15)	0.0607 (5)
H12	0.5162	1.5147	0.6104	0.073*
C13	0.1346 (2)	0.94586 (17)	0.76308 (12)	0.0500 (4)
C14	0.0520 (2)	0.78342 (16)	0.88501 (12)	0.0471 (4)
C15	−0.0600 (3)	0.51329 (16)	0.82179 (12)	0.0506 (4)
H15A	−0.1582	0.5129	0.8619	0.061*
H15B	0.0418	0.4841	0.8615	0.061*
C16	−0.1336 (2)	0.40249 (16)	0.71635 (12)	0.0433 (3)
C17	−0.1583 (2)	0.34846 (18)	0.53719 (13)	0.0531 (4)
H17	−0.1312	0.3784	0.4771	0.064*
C18	−0.2621 (2)	0.20551 (18)	0.52501 (13)	0.0556 (4)
H18	−0.3042	0.1403	0.4584	0.067*
C19	−0.3025 (2)	0.16096 (18)	0.61372 (14)	0.0571 (4)
H19	−0.3731	0.0648	0.6080	0.069*
C20	−0.2370 (2)	0.26031 (17)	0.71097 (13)	0.0504 (4)
H20	−0.2619	0.2322	0.7721	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.1197 (5)	0.0465 (3)	0.0393 (3)	0.0166 (3)	0.0220 (2)	0.00870 (19)
O1	0.1052 (10)	0.0460 (7)	0.0428 (6)	0.0006 (6)	0.0275 (6)	0.0016 (5)
N1	0.0788 (9)	0.0363 (7)	0.0391 (7)	0.0075 (6)	0.0201 (6)	0.0027 (5)
N2	0.0685 (9)	0.0363 (7)	0.0378 (7)	0.0080 (6)	0.0155 (6)	0.0060 (5)
N3	0.0621 (8)	0.0403 (7)	0.0430 (7)	0.0081 (6)	0.0142 (6)	0.0092 (6)
C1	0.0791 (12)	0.0500 (9)	0.0405 (9)	0.0038 (8)	0.0147 (8)	0.0118 (7)
C2	0.0716 (11)	0.0478 (9)	0.0434 (9)	0.0012 (8)	0.0108 (8)	0.0064 (7)
C3	0.0480 (9)	0.0461 (8)	0.0515 (9)	0.0119 (7)	0.0155 (7)	0.0127 (7)
C4	0.0560 (9)	0.0520 (9)	0.0452 (9)	0.0150 (8)	0.0118 (7)	0.0157 (7)
C5	0.0560 (9)	0.0473 (9)	0.0431 (9)	0.0114 (7)	0.0100 (7)	0.0055 (7)
C6	0.0575 (9)	0.0431 (8)	0.0427 (8)	0.0099 (7)	0.0183 (7)	0.0071 (7)
C7	0.0473 (9)	0.0477 (9)	0.0595 (10)	0.0104 (7)	0.0059 (7)	0.0178 (8)
C8	0.0716 (12)	0.0499 (10)	0.0671 (12)	0.0104 (9)	0.0075 (9)	0.0141 (9)
C9	0.0860 (14)	0.0482 (10)	0.0823 (15)	0.0106 (10)	−0.0078 (11)	0.0131 (10)
C10	0.0821 (14)	0.0581 (12)	0.0998 (17)	−0.0004 (10)	−0.0113 (12)	0.0394 (13)
C11	0.0773 (14)	0.0774 (14)	0.0834 (15)	0.0063 (11)	0.0097 (11)	0.0457 (13)
C12	0.0610 (10)	0.0598 (11)	0.0637 (11)	0.0116 (8)	0.0097 (9)	0.0257 (9)
C13	0.0611 (10)	0.0440 (9)	0.0441 (9)	0.0086 (7)	0.0191 (7)	0.0065 (7)
C14	0.0577 (9)	0.0391 (8)	0.0437 (9)	0.0104 (7)	0.0149 (7)	0.0063 (7)
C15	0.0687 (10)	0.0393 (8)	0.0433 (9)	0.0096 (7)	0.0140 (8)	0.0102 (7)
C16	0.0508 (9)	0.0384 (8)	0.0426 (8)	0.0134 (7)	0.0130 (7)	0.0088 (6)
C17	0.0648 (10)	0.0510 (9)	0.0412 (9)	0.0090 (8)	0.0139 (7)	0.0084 (7)
C18	0.0629 (10)	0.0487 (9)	0.0456 (9)	0.0049 (8)	0.0073 (8)	0.0008 (7)
C19	0.0626 (10)	0.0407 (8)	0.0597 (10)	−0.0011 (8)	0.0114 (8)	0.0078 (8)
C20	0.0604 (10)	0.0442 (9)	0.0476 (9)	0.0089 (7)	0.0161 (7)	0.0133 (7)

Geometric parameters (Å, º) top

S1—C14	1.6703 (16)	C7—C12	1.383 (2)
O1—C13	1.2147 (18)	C7—C8	1.394 (2)
N1—C13	1.3735 (19)	C8—C9	1.385 (3)
N1—C14	1.390 (2)	C8—H8	0.9300
N1—H1	0.8600	C9—C10	1.365 (3)
N2—C14	1.3102 (19)	C9—H9	0.9300
N2—C15	1.4449 (19)	C10—C11	1.368 (3)
N2—H2	0.8600	C10—H10	0.9300
N3—C16	1.3351 (19)	C11—C12	1.386 (3)
N3—C17	1.336 (2)	C11—H11	0.9300
C1—C2	1.377 (2)	C12—H12	0.9300
C1—C6	1.386 (2)	C15—C16	1.505 (2)
C1—H1A	0.9300	C15—H15A	0.9700
C2—C3	1.389 (2)	C15—H15B	0.9700
C2—H2A	0.9300	C16—C20	1.381 (2)
C3—C4	1.391 (2)	C17—C18	1.370 (2)
C3—C7	1.482 (2)	C17—H17	0.9300
C4—C5	1.375 (2)	C18—C19	1.374 (2)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.387 (2)	C19—C20	1.375 (2)
C5—H5	0.9300	C19—H19	0.9300
C6—C13	1.489 (2)	C20—H20	0.9300

C13—N1—C14	128.47 (13)	C9—C10—H10	119.9
C13—N1—H1	115.8	C11—C10—H10	119.9
C14—N1—H1	115.8	C10—C11—C12	120.4 (2)
C14—N2—C15	123.28 (13)	C10—C11—H11	119.8
C14—N2—H2	118.4	C12—C11—H11	119.8
C15—N2—H2	118.4	C7—C12—C11	120.35 (19)
C16—N3—C17	117.48 (13)	C7—C12—H12	119.8
C2—C1—C6	120.47 (15)	C11—C12—H12	119.8
C2—C1—H1A	119.8	O1—C13—N1	122.47 (14)
C6—C1—H1A	119.8	O1—C13—C6	122.08 (14)
C1—C2—C3	121.59 (15)	N1—C13—C6	115.45 (13)
C1—C2—H2A	119.2	N2—C14—N1	117.11 (13)
C3—C2—H2A	119.2	N2—C14—S1	124.42 (12)
C2—C3—C4	117.39 (14)	N1—C14—S1	118.47 (11)
C2—C3—C7	120.20 (14)	N2—C15—C16	110.45 (12)
C4—C3—C7	122.41 (14)	N2—C15—H15A	109.6
C5—C4—C3	121.30 (14)	C16—C15—H15A	109.6
C5—C4—H4	119.4	N2—C15—H15B	109.6
C3—C4—H4	119.4	C16—C15—H15B	109.6
C4—C5—C6	120.79 (15)	H15A—C15—H15B	108.1
C4—C5—H5	119.6	N3—C16—C20	122.55 (14)
C6—C5—H5	119.6	N3—C16—C15	117.53 (13)
C1—C6—C5	118.42 (14)	C20—C16—C15	119.92 (13)
C1—C6—C13	123.02 (14)	N3—C17—C18	123.61 (15)
C5—C6—C13	118.53 (14)	N3—C17—H17	118.2
C12—C7—C8	118.43 (16)	C18—C17—H17	118.2
C12—C7—C3	120.95 (16)	C17—C18—C19	118.35 (15)
C8—C7—C3	120.60 (15)	C17—C18—H18	120.8
C9—C8—C7	120.47 (19)	C19—C18—H18	120.8
C9—C8—H8	119.8	C18—C19—C20	119.16 (15)
C7—C8—H8	119.8	C18—C19—H19	120.4
C10—C9—C8	120.2 (2)	C20—C19—H19	120.4
C10—C9—H9	119.9	C19—C20—C16	118.86 (15)
C8—C9—H9	119.9	C19—C20—H20	120.6
C9—C10—C11	120.11 (19)	C16—C20—H20	120.6

C6—C1—C2—C3	0.3 (3)	C14—N1—C13—O1	6.5 (3)
C1—C2—C3—C4	−1.6 (3)	C14—N1—C13—C6	−173.11 (16)
C1—C2—C3—C7	179.29 (16)	C1—C6—C13—O1	−156.33 (17)
C2—C3—C4—C5	1.2 (2)	C5—C6—C13—O1	21.6 (2)
C7—C3—C4—C5	−179.76 (15)	C1—C6—C13—N1	23.3 (2)
C3—C4—C5—C6	0.6 (2)	C5—C6—C13—N1	−158.76 (15)
C2—C1—C6—C5	1.5 (3)	C15—N2—C14—N1	−178.94 (15)
C2—C1—C6—C13	179.51 (16)	C15—N2—C14—S1	1.9 (2)
C4—C5—C6—C1	−2.0 (2)	C13—N1—C14—N2	−3.7 (3)
C4—C5—C6—C13	179.95 (15)	C13—N1—C14—S1	175.48 (14)
C2—C3—C7—C12	141.85 (17)	C14—N2—C15—C16	170.01 (14)
C4—C3—C7—C12	−37.2 (2)	C17—N3—C16—C20	−0.1 (2)
C2—C3—C7—C8	−36.5 (2)	C17—N3—C16—C15	179.56 (14)
C4—C3—C7—C8	144.45 (17)	N2—C15—C16—N3	13.4 (2)
C12—C7—C8—C9	−1.5 (3)	N2—C15—C16—C20	−166.90 (14)
C3—C7—C8—C9	176.90 (16)	C16—N3—C17—C18	0.2 (2)
C7—C8—C9—C10	0.1 (3)	N3—C17—C18—C19	0.0 (3)
C8—C9—C10—C11	1.1 (3)	C17—C18—C19—C20	−0.3 (3)
C9—C10—C11—C12	−0.8 (3)	C18—C19—C20—C16	0.5 (3)
C8—C7—C12—C11	1.8 (3)	N3—C16—C20—C19	−0.2 (2)
C3—C7—C12—C11	−176.64 (16)	C15—C16—C20—C19	−179.91 (15)
C10—C11—C12—C7	−0.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.99	2.6681 (19)	135
N2—H2···N3	0.86	2.24	2.6488 (19)	109
N1—H1···S1ⁱ	0.86	2.79	3.4759 (17)	138

Symmetry code: (i) −x, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇N₃OS
M_r	347.43
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	7.467 (2), 9.364 (2), 13.184 (3)
α, β, γ (°)	101.529 (5), 99.113 (4), 101.543 (5)
V (Å³)	865.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.45 × 0.37 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.915, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	8243, 3036, 2561
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.101, 1.05
No. of reflections	3036
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.19

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.99	2.6681 (19)	135
N2—H2···N3	0.86	2.24	2.6488 (19)	109
N1—H1···S1ⁱ	0.86	2.79	3.4759 (17)	138

Symmetry code: (i) −x, −y+2, −z+2.

Acknowledgements

The authors thank the Ministry of Higher Education of Malaysia for the Fundamental Research Grant UKM-ST-01-FRGS-0003–2006 and Universiti Kebangsaan Malaysian for the research facilities.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
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Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97, University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
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