1-(Biphenyl-4-ylcarbon­yl)-3-(4-nitro­phen­yl)thio­urea

Yusof, M.S.M.; Wong, S.T.; Yamin, B.M.

doi:10.1107/S160053681103426X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2483

doi:10.1107/S160053681103426X

Open

access

1-(Biphenyl-4-ylcarbonyl)-3-(4-nitrophenyl)thiourea

M. Sukeri M. Yusof,^a ^* Sze Ting Wong ^a and Bohari M. Yamin ^b

^aDepartment of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu, Malaysia, and ^bSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, UKM 43500 Bangi Selangor, Malaysia
^*Correspondence e-mail: mohdsukeri@umt.edu.my

(Received 8 August 2011; accepted 21 August 2011; online 27 August 2011)

In the title compound, C₂₀H₁₅N₃O₃S, the two benzene rings of the biphenyl group form a dihedral angle of 40.11 (15)°. The conformation of the molecule is trans–cis and is stabilized by two intramolecular N—H⋯O and C—H⋯S hydrogen bonds. In the crystal structure, the molecules are linked by weak π–π stacking interactions [centroid–centroid distance = 3.991 (2) Å].

Related literature

For related structures, see: Arif &Yamin (2007 ); Yamin & Arif (2008 ). For standard bond lengths, see: Allen et al. (2003 ).

Experimental

Crystal data

C₂₀H₁₅N₃O₃S
M_r = 377.41
Monoclinic, P 2₁ /c
a = 12.154 (2) Å
b = 9.4509 (18) Å
c = 17.471 (3) Å
β = 118.133 (9)°
V = 1769.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 298 K
0.38 × 0.14 × 0.07 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.925, T_max = 0.986
9891 measured reflections
3116 independent reflections
2268 reflections with I > 2/s(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.143
S = 0.88
3116 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.90	2.633 (4)	142
C20—H20⋯S1	0.93	2.55	3.186 (4)	126

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: OLEX2 (Dolomanov et al., 2009 ), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681103426X/bx2367sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681103426X/bx2367Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681103426X/bx2367Isup3.cml

checkCIF report

Comment top

The title compound, (I) is analogous to the previously reported N-(biphenyl-4-carbonyl)-N'-(4-chlorophenyl)thiourea (II) (Yamin & Arif, 2008) except the chlorine atom in (II) is replaced by a nitro group. The bond lengths and angles are in normal ranges (Allen et al., 2003) and comparable to those previous reported (Arif & Yamin, 2007). The benzene rings (C1—C6, C7—C12, C15—C20) and thiourea moities (C14/N1/N2/S1) are all planar with maximum deviation of 0.043 (3) Å for atom N1 from the mean plane. The dihedral angle of two benzene rings of the biphenyl group are at an angle of 40.11 (15)° smaller compared in (II)(44.23 (12)°). The central thiourea fragment makes dihedral angles with the benzene-carbonyl (C7—C12) and nitrobenzene (C15—C20) rings of 16.14 (13) and 17.75 (14)°, respectively, smaller compared in (II) (55.96 (9) and 64.09 (9)°). The conformation of the molecule is trans-cis and is stabilized by two intramolecular hydrogen bonds N—H^.···O and C—H^.···S interactions. In the crystal structure, the molecules are linked by weak π-π stacking interactions, Table1 & Table2, Fig2.

Related literature top

For a related structure, see: Arif &Yamin (2007); Yamin & Arif (2008). For standard bond lengths, see: Allen et al. (2003).

Experimental top

A solution of biphenylcarbomoylisothiocyanate (2.0 g, 8.4 mmol) in 20 ml acetone was added dropwise to a two-necked round-bottomed flask containing an equimolar amount of 4-nitroaniline (1.15 g, 8.4 mmol) in 20 ml of acetone. The mixture was refluxed for about 2.5 h. The light yellow solution was filtered and the filtrate allowed to evaporate at room temperature. Light yellow crystals were obtained after five days (yield 63%, m.p.: 164–166°C).

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: OLEX2 (Dolomanov et al., 2009), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsods drawn at the 50% probability level. The hydrogen bonds are shown by dashed lines.
	Fig. 2. π-π stacking interactions. The centroids are linked by dashed lines.

1-(Biphenyl-4-ylcarbonyl)-3-(4-nitrophenyl)thiourea top

Crystal data top

C₂₀H₁₅N₃O₃S	F(000) = 784
M_r = 377.41	D_x = 1.416 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 777 reflections
a = 12.154 (2) Å	θ = 1.9–25.0°
b = 9.4509 (18) Å	µ = 0.21 mm⁻¹
c = 17.471 (3) Å	T = 298 K
β = 118.133 (9)°	Slab, light yellow
V = 1769.7 (5) Å³	0.38 × 0.14 × 0.07 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3116 independent reflections
Radiation source: fine-focus sealed tube	2268 reflections with I > 2/s(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.0°, θ_min = 1.9°
ω scan	h = −13→14
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −10→11
T_min = 0.925, T_max = 0.986	l = −20→20
9891 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 0.88	w = 1/[σ²(F_o²) + (0.0447P)² + 3.2573P] where P = (F_o² + 2F_c²)/3
3116 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₀H₁₅N₃O₃S	V = 1769.7 (5) Å³
M_r = 377.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.154 (2) Å	µ = 0.21 mm⁻¹
b = 9.4509 (18) Å	T = 298 K
c = 17.471 (3) Å	0.38 × 0.14 × 0.07 mm
β = 118.133 (9)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3116 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2268 reflections with I > 2/s(I)
T_min = 0.925, T_max = 0.986	R_int = 0.043
9891 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 0.88	Δρ_max = 0.26 e Å⁻³
3116 reflections	Δρ_min = −0.22 e Å⁻³
244 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	0.34844 (10)	−0.26185 (12)	−0.10149 (6)	0.0687 (4)
O1	0.3207 (2)	−0.5537 (3)	0.09461 (16)	0.0618 (7)
O2	1.0052 (2)	−0.1773 (3)	0.30122 (17)	0.0662 (7)
O3	0.9535 (3)	−0.0226 (3)	0.19967 (19)	0.0773 (9)
N1	0.2547 (2)	−0.4403 (3)	−0.03407 (17)	0.0445 (7)
H1	0.1906	−0.4296	−0.0842	0.053*
N2	0.4557 (2)	−0.3739 (3)	0.05899 (17)	0.0473 (7)
H2A	0.4451	−0.4353	0.0913	0.057*
N3	0.9295 (3)	−0.1246 (3)	0.2325 (2)	0.0540 (8)
C1	−0.3311 (3)	−0.7919 (4)	−0.1811 (2)	0.0524 (9)
H1A	−0.3269	−0.7079	−0.2074	0.063*
C2	−0.4442 (3)	−0.8619 (5)	−0.2122 (2)	0.0612 (10)
H2B	−0.5157	−0.8240	−0.2578	0.073*
C3	−0.4498 (4)	−0.9871 (5)	−0.1752 (3)	0.0674 (12)
H3A	−0.5255	−1.0347	−0.1962	0.081*
C4	−0.3461 (4)	−1.0434 (5)	−0.1080 (3)	0.0717 (12)
H4	−0.3508	−1.1292	−0.0837	0.086*
C5	−0.2324 (4)	−0.9710 (4)	−0.0758 (2)	0.0595 (10)
H5	−0.1617	−1.0090	−0.0295	0.071*
C6	−0.2238 (3)	−0.8443 (3)	−0.1117 (2)	0.0423 (8)
C7	−0.1055 (3)	−0.7659 (3)	−0.0786 (2)	0.0402 (7)
C8	−0.0235 (3)	−0.7554 (4)	0.0100 (2)	0.0468 (8)
H8	−0.0436	−0.7995	0.0493	0.056*
C9	0.0873 (3)	−0.6809 (4)	0.0405 (2)	0.0462 (8)
H9	0.1410	−0.6763	0.0999	0.055*
C10	0.1184 (3)	−0.6134 (3)	−0.0165 (2)	0.0398 (7)
C11	0.0382 (3)	−0.6242 (3)	−0.1049 (2)	0.0435 (8)
H11	0.0586	−0.5800	−0.1440	0.052*
C12	−0.0709 (3)	−0.6991 (4)	−0.1351 (2)	0.0471 (8)
H12	−0.1229	−0.7055	−0.1946	0.056*
C13	0.2392 (3)	−0.5352 (3)	0.0202 (2)	0.0450 (8)
C14	0.3579 (3)	−0.3590 (3)	−0.0200 (2)	0.0433 (8)
C15	0.5734 (3)	−0.3067 (3)	0.0989 (2)	0.0407 (8)
C16	0.6628 (3)	−0.3681 (4)	0.1744 (2)	0.0458 (8)
H16	0.6438	−0.4499	0.1954	0.055*
C17	0.7800 (3)	−0.3090 (4)	0.2191 (2)	0.0484 (8)
H17	0.8405	−0.3504	0.2698	0.058*
C18	0.8055 (3)	−0.1871 (4)	0.1869 (2)	0.0452 (8)
C19	0.7179 (3)	−0.1240 (4)	0.1130 (2)	0.0557 (9)
H19	0.7372	−0.0418	0.0926	0.067*
C20	0.5997 (3)	−0.1833 (4)	0.0686 (2)	0.0561 (9)
H20	0.5387	−0.1401	0.0188	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0687 (7)	0.0718 (7)	0.0517 (6)	−0.0203 (6)	0.0169 (5)	0.0114 (5)
O1	0.0406 (14)	0.0756 (18)	0.0498 (15)	−0.0105 (12)	0.0054 (12)	0.0164 (13)
O2	0.0439 (15)	0.0724 (18)	0.0605 (17)	−0.0035 (13)	0.0068 (13)	−0.0029 (14)
O3	0.0691 (19)	0.075 (2)	0.0768 (19)	−0.0285 (16)	0.0255 (16)	0.0006 (16)
N1	0.0330 (15)	0.0523 (17)	0.0412 (15)	−0.0026 (13)	0.0118 (13)	0.0020 (13)
N2	0.0439 (17)	0.0477 (16)	0.0481 (16)	−0.0050 (13)	0.0198 (14)	0.0046 (13)
N3	0.0472 (19)	0.056 (2)	0.0563 (19)	−0.0065 (15)	0.0223 (17)	−0.0103 (16)
C1	0.045 (2)	0.055 (2)	0.050 (2)	−0.0013 (17)	0.0155 (18)	−0.0062 (17)
C2	0.039 (2)	0.075 (3)	0.060 (2)	−0.0044 (19)	0.0147 (18)	−0.022 (2)
C3	0.050 (2)	0.082 (3)	0.076 (3)	−0.028 (2)	0.034 (2)	−0.032 (2)
C4	0.082 (3)	0.066 (3)	0.075 (3)	−0.026 (2)	0.043 (3)	−0.006 (2)
C5	0.055 (2)	0.058 (2)	0.058 (2)	−0.0060 (19)	0.0209 (19)	0.0014 (19)
C6	0.0398 (19)	0.0454 (19)	0.0434 (18)	−0.0018 (15)	0.0211 (16)	−0.0078 (15)
C7	0.0355 (18)	0.0381 (18)	0.0447 (18)	0.0028 (14)	0.0171 (15)	−0.0019 (14)
C8	0.0411 (19)	0.055 (2)	0.0437 (19)	−0.0005 (16)	0.0192 (16)	0.0033 (16)
C9	0.0369 (18)	0.060 (2)	0.0349 (17)	−0.0019 (16)	0.0112 (15)	0.0011 (16)
C10	0.0333 (17)	0.0415 (18)	0.0416 (18)	0.0054 (14)	0.0152 (15)	0.0004 (14)
C11	0.0423 (19)	0.049 (2)	0.0438 (19)	0.0019 (16)	0.0239 (16)	0.0039 (15)
C12	0.0409 (19)	0.056 (2)	0.0356 (17)	−0.0030 (16)	0.0112 (15)	−0.0014 (15)
C13	0.0371 (19)	0.0444 (19)	0.047 (2)	0.0019 (15)	0.0151 (17)	0.0007 (16)
C14	0.0384 (19)	0.0388 (18)	0.0474 (19)	0.0024 (15)	0.0160 (16)	−0.0037 (15)
C15	0.0370 (18)	0.0422 (18)	0.0447 (18)	−0.0019 (15)	0.0206 (16)	−0.0044 (15)
C16	0.042 (2)	0.047 (2)	0.050 (2)	−0.0038 (16)	0.0229 (17)	0.0040 (16)
C17	0.043 (2)	0.055 (2)	0.0412 (19)	0.0029 (17)	0.0151 (16)	0.0006 (16)
C18	0.0373 (18)	0.0473 (19)	0.049 (2)	−0.0056 (16)	0.0185 (16)	−0.0078 (16)
C19	0.054 (2)	0.046 (2)	0.061 (2)	−0.0100 (18)	0.022 (2)	0.0050 (18)
C20	0.046 (2)	0.054 (2)	0.057 (2)	−0.0009 (18)	0.0153 (18)	0.0103 (18)

Geometric parameters (Å, º) top

S1—C14	1.652 (3)	C6—C7	1.472 (4)
O1—C13	1.219 (4)	C7—C12	1.393 (4)
O2—N3	1.222 (4)	C7—C8	1.394 (4)
O3—N3	1.226 (4)	C8—C9	1.384 (4)
N1—C13	1.382 (4)	C8—H8	0.9300
N1—C14	1.391 (4)	C9—C10	1.378 (4)
N1—H1	0.8605	C9—H9	0.9300
N2—C14	1.338 (4)	C10—C11	1.387 (4)
N2—C15	1.413 (4)	C10—C13	1.492 (4)
N2—H2A	0.8601	C11—C12	1.370 (4)
N3—C18	1.457 (4)	C11—H11	0.9300
C1—C2	1.385 (5)	C12—H12	0.9300
C1—C6	1.388 (4)	C15—C20	1.379 (5)
C1—H1A	0.9300	C15—C16	1.381 (4)
C2—C3	1.365 (6)	C16—C17	1.379 (4)
C2—H2B	0.9300	C16—H16	0.9300
C3—C4	1.361 (6)	C17—C18	1.380 (5)
C3—H3A	0.9300	C17—H17	0.9300
C4—C5	1.400 (5)	C18—C19	1.363 (5)
C4—H4	0.9300	C19—C20	1.389 (5)
C5—C6	1.378 (5)	C19—H19	0.9300
C5—H5	0.9300	C20—H20	0.9300

C13—N1—C14	129.9 (3)	C8—C9—H9	119.8
C13—N1—H1	115.1	C9—C10—C11	118.8 (3)
C14—N1—H1	115.1	C9—C10—C13	117.9 (3)
C14—N2—C15	131.5 (3)	C11—C10—C13	123.3 (3)
C14—N2—H2A	114.3	C12—C11—C10	120.7 (3)
C15—N2—H2A	114.2	C12—C11—H11	119.6
O2—N3—O3	123.1 (3)	C10—C11—H11	119.6
O2—N3—C18	118.5 (3)	C11—C12—C7	121.5 (3)
O3—N3—C18	118.4 (3)	C11—C12—H12	119.3
C2—C1—C6	121.5 (4)	C7—C12—H12	119.3
C2—C1—H1A	119.3	O1—C13—N1	121.3 (3)
C6—C1—H1A	119.3	O1—C13—C10	121.9 (3)
C3—C2—C1	119.4 (4)	N1—C13—C10	116.8 (3)
C3—C2—H2B	120.3	N2—C14—N1	114.4 (3)
C1—C2—H2B	120.3	N2—C14—S1	127.9 (3)
C4—C3—C2	120.9 (4)	N1—C14—S1	117.7 (2)
C4—C3—H3A	119.5	C20—C15—C16	120.2 (3)
C2—C3—H3A	119.5	C20—C15—N2	123.7 (3)
C3—C4—C5	119.5 (4)	C16—C15—N2	116.1 (3)
C3—C4—H4	120.2	C17—C16—C15	120.5 (3)
C5—C4—H4	120.2	C17—C16—H16	119.7
C6—C5—C4	120.9 (4)	C15—C16—H16	119.7
C6—C5—H5	119.5	C16—C17—C18	118.5 (3)
C4—C5—H5	119.5	C16—C17—H17	120.7
C5—C6—C1	117.8 (3)	C18—C17—H17	120.7
C5—C6—C7	121.9 (3)	C19—C18—C17	121.7 (3)
C1—C6—C7	120.3 (3)	C19—C18—N3	119.0 (3)
C12—C7—C8	117.2 (3)	C17—C18—N3	119.2 (3)
C12—C7—C6	121.0 (3)	C18—C19—C20	119.6 (3)
C8—C7—C6	121.7 (3)	C18—C19—H19	120.2
C9—C8—C7	121.3 (3)	C20—C19—H19	120.2
C9—C8—H8	119.3	C15—C20—C19	119.5 (3)
C7—C8—H8	119.3	C15—C20—H20	120.3
C10—C9—C8	120.4 (3)	C19—C20—H20	120.3
C10—C9—H9	119.8

C6—C1—C2—C3	−1.8 (5)	C9—C10—C13—O1	15.8 (5)
C1—C2—C3—C4	0.5 (6)	C11—C10—C13—O1	−162.5 (3)
C2—C3—C4—C5	0.7 (6)	C9—C10—C13—N1	−164.2 (3)
C3—C4—C5—C6	−0.6 (6)	C11—C10—C13—N1	17.4 (5)
C4—C5—C6—C1	−0.6 (5)	C15—N2—C14—N1	−177.0 (3)
C4—C5—C6—C7	179.7 (3)	C15—N2—C14—S1	5.4 (5)
C2—C1—C6—C5	1.8 (5)	C13—N1—C14—N2	−1.4 (5)
C2—C1—C6—C7	−178.5 (3)	C13—N1—C14—S1	176.4 (3)
C5—C6—C7—C12	139.9 (3)	C14—N2—C15—C20	16.4 (5)
C1—C6—C7—C12	−39.8 (5)	C14—N2—C15—C16	−166.6 (3)
C5—C6—C7—C8	−40.0 (5)	C20—C15—C16—C17	−1.7 (5)
C1—C6—C7—C8	140.3 (3)	N2—C15—C16—C17	−178.8 (3)
C12—C7—C8—C9	0.5 (5)	C15—C16—C17—C18	0.4 (5)
C6—C7—C8—C9	−179.7 (3)	C16—C17—C18—C19	0.5 (5)
C7—C8—C9—C10	0.7 (5)	C16—C17—C18—N3	−179.0 (3)
C8—C9—C10—C11	−1.3 (5)	O2—N3—C18—C19	176.0 (3)
C8—C9—C10—C13	−179.8 (3)	O3—N3—C18—C19	−4.9 (5)
C9—C10—C11—C12	0.7 (5)	O2—N3—C18—C17	−4.5 (5)
C13—C10—C11—C12	179.1 (3)	O3—N3—C18—C17	174.6 (3)
C10—C11—C12—C7	0.5 (5)	C17—C18—C19—C20	−0.1 (5)
C8—C7—C12—C11	−1.1 (5)	N3—C18—C19—C20	179.5 (3)
C6—C7—C12—C11	179.0 (3)	C16—C15—C20—C19	2.2 (5)
C14—N1—C13—O1	3.9 (5)	N2—C15—C20—C19	179.0 (3)
C14—N1—C13—C10	−176.1 (3)	C18—C19—C20—C15	−1.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.90	2.633 (4)	142
C20—H20···S1	0.93	2.55	3.186 (4)	126

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅N₃O₃S
M_r	377.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.154 (2), 9.4509 (18), 17.471 (3)
β (°)	118.133 (9)
V (Å³)	1769.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.38 × 0.14 × 0.07

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.925, 0.986
No. of measured, independent and observed [I > 2/s(I)] reflections	9891, 3116, 2268
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.143, 0.88
No. of reflections	3116
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.22

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.90	2.633 (4)	142
C20—H20···S1	0.93	2.55	3.186 (4)	126

π–π stacking interaction in (I) top

Cg1 is the centroid of the C7–C12 ring, ϕ is the dihedral angle (°) between the planes of the rings, d is the distance (Å) between the ring centroids and Δ is the displacement (Å) of the centroid of ring 2 relative to the intersection point of the normal to the centroid of ring 1 and the least-squares plane of ring 2.

Ring 1	Ring 2	ϕ	d	Δ
Cg1	Cg1i	0.0	3.991 (2)	1.778

Symmetry code: (i) -x, -1-y, -z

Acknowledgements

The authors thank the Malaysian Government, Universiti Kebangsaan Malaysia, Faculty of Science and Technology, Universiti Malaysia Terengganu and the Ministry of Higher Education, Malaysia for research grant Nos. UKM-GUP-NBT-08-27-110 and FRGS 59178.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (2003). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. Google Scholar
Arif, M. A. M. & Yamin, B. M. (2007). Acta Cryst. E63, o3594. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals 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. & Arif, M. A. M. (2008). Acta Cryst. E64, o104. CrossRef IUCr Journals Google Scholar