1,1-Dibenzyl-3-(4-fluoro­benzo­yl)thio­urea

Nasir, M.F.M.; Hassan, I.N.; Wan Daud, W.R.; Yamin, B.M.; Kassim, M.B.

doi:10.1107/S1600536811026687

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1987

doi:10.1107/S1600536811026687

Open

access

1,1-Dibenzyl-3-(4-fluorobenzoyl)thiourea

Mohd Faizal Md Nasir,^a Ibrahim N. Hassan,^a ^* Wan Ramli Wan Daud,^b,^a Bohari M. Yamin ^c and Mohammad B. Kassim ^c,^a

^aFuel Cell Institute, Universiti Kebangsaan Malaysia, UKM 43600 Bangi Selangor, Malaysia, ^bDepartment of Chemical and Process Engineering, Faculty of Engineering, Universiti Kebangsaan Malaysia, UKM 43600 Bangi Selangor, Malaysia, and ^cSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, UKM 43600 Bangi Selangor, Malaysia
^*Correspondence e-mail: ibnhum@gmail.com

(Received 28 June 2011; accepted 4 July 2011; online 9 July 2011)

In the title compound, C₂₂H₁₉FN₂OS, the 2-fluorobenzoyl group adopts a trans conformation with respect to the thiono S atom across the N—C bond. In the crystal, intermolecular N—H⋯S, C—H⋯S and C—H⋯O hydrogen bonds link the molecules, forming a two-dimensional network parallel to (101).

Related literature

For standard bond lengths, see: Allen et al. (1987 ). For related structures, see: Nasir et al. (2011 ); Yamin & Hassan (2004 ); Hassan et al. (2008a ,b ,c , 2009 ). For the synthesis, see: Hassan et al. (2008a).

Experimental

Crystal data

C₂₂H₁₉FN₂OS
M_r = 378.45
Monoclinic, P 2₁ /n
a = 10.683 (3) Å
b = 7.026 (2) Å
c = 26.435 (7) Å
β = 101.100 (6)°
V = 1946.9 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 298 K
0.42 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.925, T_max = 0.967
8644 measured reflections
3425 independent reflections
2659 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.138
S = 1.15
3425 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1ⁱ	0.86	2.61	3.422 (2)	159
C1—H1A⋯S1ⁱ	0.93	2.87	3.727 (3)	154
C4—H4⋯O1ⁱⁱ	0.93	2.50	3.322 (4)	147
Symmetry codes: (i) -x+1, -y, -z; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), XP in SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811026687/dn2702sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026687/dn2702Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026687/dn2702Isup3.cml

checkCIF report

Comment top

The title compound, I, is a thiourea derivative of dibenzylamine analogous to our previous reported, 1,1-sibenzyl-3-(3-chlorobenzoyl)thiourea, II (Nasir et al. 2011). The molecule maintains the the same trans and cis conformation for both the 3-fluorobenzoyl and the dibenzylamine groups, respectively, relative to the S atom across the N2—C8 bond (Fig 1). The dihedral angle between the phenyl ring, (C1—C6), and the thiourea fragment, (S1/N1/N2/C8) is 70.95 (13)° , whereas in II was 72.9 (2)°. The bond lengths and angles in the molecules are in normal ranges (Allen et al., 1987) and comparable with those of II. However, the C=S bond length [1.678 (2)Å] is slightly longer than that of (II) [1.672 (6)Å]

Both phenyl rings, [C10/C11/C12/C13/C14/C15] and [C17/C18/C19/C20/C21/C22] are essentially planar and are twisted to each other by a dihedral angle of 22.4 (4)°. The intermolecular N1—H1···S1, C1—H1A···S and C4—H4···O1 hydrogen bonds (Table 1,) links the molecules into two dimensional ribbon parallel to the (1 0 1) plane (Fig 2).

Related literature top

For standard bond lengths, see: Allen et al. (1987). For related structures, see: Nasir et al. (2011); Yamin & Hassan (2004); Hassan et al. (2008a,b,c, 2009). For the synthesis, see: Hassan et al. (2008a).

Experimental top

The title compound was synthesized according to a previously reported compound (Hassan et al., 2008a). A colourless crystal, suitable for X-ray crystallography, was obtained by a slow evaporation from ethanolic solution at room temperature (yield 87%).

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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), XP in SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), with the atoms labeling scheme and displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing of (I) view down the b axis. H bonds are shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity.

1,1-Dibenzyl-3-(4-fluorobenzoyl)thiourea top

Crystal data top

C₂₂H₁₉FN₂OS	F(000) = 792
M_r = 378.45	D_x = 1.291 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 410 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.683 (3) Å	Cell parameters from 2659 reflections
b = 7.026 (2) Å	θ = 2.0–25.0°
c = 26.435 (7) Å	µ = 0.19 mm⁻¹
β = 101.100 (6)°	T = 298 K
V = 1946.9 (10) Å³	Block, colourless
Z = 4	0.42 × 0.21 × 0.18 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3425 independent reflections
Radiation source: fine-focus sealed tube	2659 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −12→8
T_min = 0.925, T_max = 0.967	k = −8→8
8644 measured reflections	l = −31→28

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0542P)² + 0.5146P] where P = (F_o² + 2F_c²)/3
3425 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₂H₁₉FN₂OS	V = 1946.9 (10) Å³
M_r = 378.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.683 (3) Å	µ = 0.19 mm⁻¹
b = 7.026 (2) Å	T = 298 K
c = 26.435 (7) Å	0.42 × 0.21 × 0.18 mm
β = 101.100 (6)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3425 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2659 reflections with I > 2σ(I)
T_min = 0.925, T_max = 0.967	R_int = 0.027
8644 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.15	Δρ_max = 0.25 e Å⁻³
3425 reflections	Δρ_min = −0.23 e Å⁻³
244 parameters

Special details top

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
F1	0.8992 (2)	−0.7024 (3)	0.17795 (9)	0.1137 (8)
S1	0.47635 (8)	0.26603 (10)	0.02677 (3)	0.0641 (3)
O1	0.5719 (2)	0.0400 (3)	0.17142 (7)	0.0736 (6)
N1	0.5164 (2)	−0.0377 (3)	0.08698 (7)	0.0502 (6)
H1	0.5210	−0.1222	0.0639	0.060*
N2	0.3452 (2)	0.1514 (3)	0.09743 (7)	0.0453 (5)
C1	0.6626 (3)	−0.3835 (4)	0.11002 (10)	0.0570 (7)
H1A	0.6047	−0.3773	0.0789	0.068*
C2	0.7407 (3)	−0.5402 (5)	0.12067 (12)	0.0697 (8)
H2	0.7369	−0.6391	0.0970	0.084*
C3	0.8236 (3)	−0.5463 (5)	0.16670 (13)	0.0742 (9)
C4	0.8339 (3)	−0.4041 (6)	0.20216 (12)	0.0807 (10)
H4	0.8924	−0.4120	0.2331	0.097*
C5	0.7554 (3)	−0.2481 (5)	0.19116 (10)	0.0694 (9)
H5	0.7605	−0.1501	0.2151	0.083*
C6	0.6688 (2)	−0.2352 (4)	0.14481 (9)	0.0495 (6)
C7	0.5840 (2)	−0.0665 (4)	0.13658 (9)	0.0507 (7)
C8	0.4407 (3)	0.1238 (3)	0.07298 (8)	0.0460 (6)
C9	0.2742 (3)	0.3312 (4)	0.09357 (10)	0.0532 (7)
H9A	0.1842	0.3052	0.0815	0.064*
H9B	0.3027	0.4123	0.0683	0.064*
C10	0.2914 (3)	0.4349 (3)	0.14432 (9)	0.0482 (6)
C11	0.4099 (3)	0.4550 (4)	0.17540 (11)	0.0627 (8)
H11	0.4801	0.3968	0.1659	0.075*
C12	0.4261 (4)	0.5594 (5)	0.22019 (12)	0.0768 (10)
H12	0.5069	0.5718	0.2406	0.092*
C13	0.3240 (4)	0.6450 (4)	0.23477 (12)	0.0796 (10)
H13	0.3351	0.7164	0.2649	0.096*
C14	0.2052 (4)	0.6251 (4)	0.20481 (13)	0.0776 (10)
H14	0.1352	0.6823	0.2148	0.093*
C15	0.1887 (3)	0.5196 (4)	0.15949 (11)	0.0625 (8)
H15	0.1076	0.5062	0.1393	0.075*
C16	0.2919 (3)	0.0015 (4)	0.12613 (9)	0.0506 (7)
H16A	0.2790	0.0517	0.1589	0.061*
H16B	0.3517	−0.1036	0.1330	0.061*
C17	0.1667 (3)	−0.0689 (4)	0.09543 (9)	0.0521 (7)
C18	0.0539 (3)	−0.0329 (5)	0.11120 (12)	0.0716 (9)
H18	0.0539	0.0402	0.1405	0.086*
C19	−0.0598 (3)	−0.1044 (7)	0.08383 (17)	0.0976 (12)
H19	−0.1357	−0.0802	0.0950	0.117*
C20	−0.0607 (5)	−0.2105 (7)	0.04053 (17)	0.1034 (14)
H20	−0.1371	−0.2595	0.0224	0.124*
C21	0.0496 (5)	−0.2446 (5)	0.02384 (13)	0.0921 (12)
H21	0.0482	−0.3150	−0.0060	0.111*
C22	0.1643 (3)	−0.1750 (4)	0.05112 (11)	0.0680 (8)
H22	0.2398	−0.1996	0.0397	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1048 (16)	0.1189 (18)	0.1105 (16)	0.0546 (14)	0.0040 (13)	0.0346 (14)
S1	0.1037 (6)	0.0484 (4)	0.0428 (4)	−0.0095 (4)	0.0210 (4)	0.0047 (3)
O1	0.0912 (15)	0.0817 (15)	0.0405 (10)	0.0164 (12)	−0.0058 (10)	−0.0154 (10)
N1	0.0710 (14)	0.0460 (12)	0.0316 (10)	0.0060 (11)	0.0050 (10)	−0.0024 (9)
N2	0.0605 (13)	0.0358 (11)	0.0379 (11)	0.0003 (10)	0.0055 (10)	0.0029 (8)
C1	0.0627 (18)	0.0552 (17)	0.0482 (15)	0.0041 (15)	−0.0013 (13)	0.0088 (13)
C2	0.075 (2)	0.063 (2)	0.0670 (19)	0.0095 (17)	0.0033 (16)	0.0058 (15)
C3	0.064 (2)	0.087 (2)	0.072 (2)	0.0230 (18)	0.0127 (17)	0.0279 (19)
C4	0.064 (2)	0.121 (3)	0.0510 (18)	0.020 (2)	−0.0025 (15)	0.020 (2)
C5	0.0630 (18)	0.099 (3)	0.0424 (15)	0.0080 (19)	0.0008 (14)	0.0019 (15)
C6	0.0500 (15)	0.0624 (17)	0.0360 (13)	−0.0023 (14)	0.0080 (11)	0.0092 (12)
C7	0.0567 (16)	0.0580 (17)	0.0350 (13)	−0.0042 (14)	0.0027 (12)	−0.0001 (12)
C8	0.0644 (17)	0.0389 (14)	0.0309 (12)	−0.0067 (13)	−0.0007 (12)	−0.0060 (10)
C9	0.0685 (18)	0.0413 (15)	0.0468 (14)	0.0062 (14)	0.0038 (13)	0.0037 (11)
C10	0.0657 (17)	0.0346 (13)	0.0452 (14)	−0.0024 (13)	0.0125 (13)	0.0041 (11)
C11	0.072 (2)	0.0539 (18)	0.0614 (17)	−0.0025 (15)	0.0122 (15)	−0.0097 (14)
C12	0.101 (3)	0.065 (2)	0.0594 (19)	−0.012 (2)	0.0029 (18)	−0.0140 (16)
C13	0.143 (3)	0.0475 (19)	0.0521 (18)	−0.005 (2)	0.029 (2)	−0.0051 (14)
C14	0.118 (3)	0.0539 (19)	0.074 (2)	0.018 (2)	0.051 (2)	0.0056 (16)
C15	0.076 (2)	0.0505 (17)	0.0659 (18)	0.0077 (16)	0.0252 (16)	0.0086 (14)
C16	0.0652 (17)	0.0459 (15)	0.0415 (13)	0.0018 (13)	0.0126 (12)	0.0053 (11)
C17	0.0682 (18)	0.0428 (15)	0.0455 (14)	−0.0060 (14)	0.0114 (13)	0.0071 (12)
C18	0.074 (2)	0.078 (2)	0.0655 (19)	−0.0069 (18)	0.0196 (17)	0.0071 (16)
C19	0.067 (2)	0.127 (4)	0.098 (3)	−0.021 (2)	0.014 (2)	0.022 (3)
C20	0.100 (3)	0.116 (3)	0.083 (3)	−0.051 (3)	−0.011 (2)	0.022 (2)
C21	0.135 (4)	0.074 (2)	0.060 (2)	−0.038 (3)	0.001 (2)	−0.0021 (17)
C22	0.092 (2)	0.0541 (17)	0.0564 (17)	−0.0092 (17)	0.0109 (16)	−0.0003 (14)

Geometric parameters (Å, º) top

F1—C3	1.360 (4)	C10—C11	1.376 (4)
S1—C8	1.678 (3)	C11—C12	1.375 (4)
O1—C7	1.213 (3)	C11—H11	0.9300
N1—C7	1.385 (3)	C12—C13	1.365 (5)
N1—C8	1.401 (3)	C12—H12	0.9300
N1—H1	0.8600	C13—C14	1.367 (5)
N2—C8	1.323 (3)	C13—H13	0.9300
N2—C9	1.467 (3)	C14—C15	1.391 (4)
N2—C16	1.475 (3)	C14—H14	0.9300
C1—C2	1.378 (4)	C15—H15	0.9300
C1—C6	1.383 (4)	C16—C17	1.508 (4)
C1—H1A	0.9300	C16—H16A	0.9700
C2—C3	1.361 (4)	C16—H16B	0.9700
C2—H2	0.9300	C17—C18	1.372 (4)
C3—C4	1.360 (5)	C17—C22	1.385 (4)
C4—C5	1.376 (4)	C18—C19	1.383 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.389 (4)	C19—C20	1.364 (6)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.482 (4)	C20—C21	1.356 (6)
C9—C10	1.507 (3)	C20—H20	0.9300
C9—H9A	0.9700	C21—C22	1.386 (5)
C9—H9B	0.9700	C21—H21	0.9300
C10—C15	1.375 (4)	C22—H22	0.9300

C7—N1—C8	122.6 (2)	C12—C11—C10	121.2 (3)
C7—N1—H1	118.7	C12—C11—H11	119.4
C8—N1—H1	118.7	C10—C11—H11	119.4
C8—N2—C9	122.0 (2)	C13—C12—C11	120.2 (3)
C8—N2—C16	123.8 (2)	C13—C12—H12	119.9
C9—N2—C16	113.9 (2)	C11—C12—H12	119.9
C2—C1—C6	121.1 (3)	C12—C13—C14	119.6 (3)
C2—C1—H1A	119.4	C12—C13—H13	120.2
C6—C1—H1A	119.4	C14—C13—H13	120.2
C3—C2—C1	118.2 (3)	C13—C14—C15	120.2 (3)
C3—C2—H2	120.9	C13—C14—H14	119.9
C1—C2—H2	120.9	C15—C14—H14	119.9
C4—C3—F1	118.4 (3)	C10—C15—C14	120.4 (3)
C4—C3—C2	123.0 (3)	C10—C15—H15	119.8
F1—C3—C2	118.5 (3)	C14—C15—H15	119.8
C3—C4—C5	118.3 (3)	N2—C16—C17	110.32 (19)
C3—C4—H4	120.8	N2—C16—H16A	109.6
C5—C4—H4	120.8	C17—C16—H16A	109.6
C4—C5—C6	120.9 (3)	N2—C16—H16B	109.6
C4—C5—H5	119.5	C17—C16—H16B	109.6
C6—C5—H5	119.5	H16A—C16—H16B	108.1
C1—C6—C5	118.4 (3)	C18—C17—C22	118.8 (3)
C1—C6—C7	123.7 (2)	C18—C17—C16	121.1 (3)
C5—C6—C7	117.8 (3)	C22—C17—C16	120.1 (3)
O1—C7—N1	121.1 (2)	C17—C18—C19	120.5 (3)
O1—C7—C6	122.2 (2)	C17—C18—H18	119.7
N1—C7—C6	116.7 (2)	C19—C18—H18	119.7
N2—C8—N1	116.7 (2)	C20—C19—C18	120.1 (4)
N2—C8—S1	124.9 (2)	C20—C19—H19	120.0
N1—C8—S1	118.3 (2)	C18—C19—H19	120.0
N2—C9—C10	112.4 (2)	C21—C20—C19	120.2 (4)
N2—C9—H9A	109.1	C21—C20—H20	119.9
C10—C9—H9A	109.1	C19—C20—H20	119.9
N2—C9—H9B	109.1	C20—C21—C22	120.3 (4)
C10—C9—H9B	109.1	C20—C21—H21	119.8
H9A—C9—H9B	107.8	C22—C21—H21	119.8
C15—C10—C11	118.4 (3)	C17—C22—C21	120.0 (3)
C15—C10—C9	120.1 (3)	C17—C22—H22	120.0
C11—C10—C9	121.5 (3)	C21—C22—H22	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···S1	0.97	2.55	3.076 (3)	114
N1—H1···S1ⁱ	0.86	2.61	3.422 (2)	159
C1—H1A···S1ⁱ	0.93	2.87	3.727 (3)	154
C4—H4···O1ⁱⁱ	0.93	2.50	3.322 (4)	147

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₉FN₂OS
M_r	378.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.683 (3), 7.026 (2), 26.435 (7)
β (°)	101.100 (6)
V (Å³)	1946.9 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.42 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.925, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	8644, 3425, 2659
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.138, 1.15
No. of reflections	3425
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.23

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), XP in SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···S1	0.97	2.55	3.076 (3)	114
N1—H1···S1ⁱ	0.86	2.61	3.422 (2)	159
C1—H1A···S1ⁱ	0.93	2.87	3.727 (3)	154
C4—H4···O1ⁱⁱ	0.93	2.50	3.322 (4)	147

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

Acknowledgements

The authors thank Universiti Kebangsaan Malaysia for providing facilities and grants (postdoctoral for INH, UKM-GUP-BTT-07–30-190 and UKM-OUP-TK-16– 73/2010&2011 for MBK sabbatical leave). They also expresstheir appreciation to the Kementerian Pengajian Tinggi, Malaysia, for the research fund No. UKM-ST-06-FRGS0111–2009.

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
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2008a). Acta Cryst. E64, o1727. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2008b). Acta Cryst. E64, o2083. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2008c). Acta Cryst. E64, o2167. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2009). Acta Cryst. E65, o3078. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nasir, M. F. M., Hassan, I. N., Wan Daud, W. R., Yamin, B. M. & Kassim, M. B. (2011). Acta Cryst. E67, o1218. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yamin, B. M. & Hassan, I. N. (2004). Acta Cryst. E60, o2513–o2514. Web of Science CSD CrossRef IUCr Journals Google Scholar