1-(Biphenyl-4-ylcarbon­yl)-3-(2-chloro-4-nitro­phen­yl)thio­urea

Yusof, M.S.M.; Yamin, B.M.; Ngah, N.

doi:10.1107/S1600536812016686

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1485

doi:10.1107/S1600536812016686

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1-(Biphenyl-4-ylcarbonyl)-3-(2-chloro-4-nitrophenyl)thiourea

M. Sukeri M. Yusof,^a Bohari M. Yamin ^b and Nurziana Ngah ^c ^*

^aDepartment of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, Menggabang Telipot, 21030 Kuala Terengganu, Malaysia, ^bSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, UKM 43600 Bangi Selangor, Malaysia, and ^cKulliyyah of Science, International Islamic University Malaysia, Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia
^*Correspondence e-mail: nurziana@iium.edu.my

(Received 3 April 2012; accepted 17 April 2012; online 21 April 2012)

The benzene rings of the biphenyl group in the title compound, C₂₀H₁₄ClN₃O₃S, are nearly coplanar [maximum deviation = 0.20 (3) Å]. The mean plane of the biphenyl group forms a dihedral angle of 5.24 (7)° with the aromatic ring of the nitrochlorobenzene group. Intramolecular N—H⋯Cl, N—H⋯O and C—H⋯S hydrogen bonds stabilize the cis–trans conformation of the molecule. In the crystal, molecules are linked by C—H⋯O and C—H⋯S hydrogen bonds into mutually interwoven corrugated layers parallel to (10-2).

Related literature

For a related structure, see: Yusof et al. (2011 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₁₄ClN₃O₃S
M_r = 411.85
Monoclinic, P 2₁ /c
a = 10.889 (2) Å
b = 5.4502 (10) Å
c = 30.532 (5) Å
β = 99.202 (4)°
V = 1788.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 298 K
0.35 × 0.13 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.885, T_max = 0.972
9537 measured reflections
3154 independent reflections
2704 reflections with I > 2/s(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.137
S = 1.16
3154 reflections
253 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl1	0.86	2.43	2.938 (2)	118
N2—H2A⋯O1	0.86	1.87	2.608 (3)	143
C16—H16A⋯S1	0.93	2.53	3.208 (3)	130
C10—H10A⋯O3ⁱ	0.93	2.57	3.354 (4)	142
C17—H17A⋯S1ⁱⁱ	0.93	2.77	3.673 (3)	165
Symmetry codes: (i) $[x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812016686/rz2737sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016686/rz2737Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812016686/rz2737Isup3.cml

checkCIF report

Comment top

The title compound, (I), is similiar to the previously reported compound 1-(biphenyl-4-yl-carbonyl)-3-(4-nitrophenyl)thiourea (II) (Yusof et al., 2011) except for the presence of a chlorine atom at 2-position of the nitrobenzene ring. The bond lengths and angles are in normal ranges (Allen et al. 1987) and comparable to those reported for (II). The molecule (Fig. 1) is essentially planar, with a maximum deviation of 0.076 (2) Å for atom N1. The introduction of a chlorine substituent at the 2-position of the nitrobenzene ring makes the two benzene rings in biphenyl group nearly coplanar, forming a dihedral angle of 1.02 (14)° compared to that of 40.11 (15)° observed in II. The thiourea moiety makes dihedral angle of 6.15 (10)° and 0.92 (10)° with the C1—C6 and C15—C20 rings, respectively, compared to the corresponding angles of 16.14 (13)° and 17.75 (14)° in II. The cis-trans conformation of the molecule is stabilized by intramolecular N2—H2A···Cl1, N2—H2A···O1 and C16—H16A···S1 hydrogen interactions (Table 1). In the crystal structure (Fig. 2), the molecules interact through intermolecular C—H···O and C—H···S hydrogen bonds to form mutually interwoven corrugated layers parallel to the (1 0 -2) plane.

Related literature top

For a related structure, see: Yusof et al. (2011). For bond-length data, see: Allen et al. (1987).

Experimental top

An acetone (30 ml) solution of 2-chloro-4-nitroaniline (1.60 g, 9.5 mmol) was added to a round-bottom flask containing 4-biphenylcarbonyl chloride (2.00 g, 9.5 mmol) and ammonium thiocyanate (0.70 g, 9.5 mmol). The mixture was refluxed for 2.5 h then filtered off and left to evaporate at room temperature. The yellowish precipitate obtained was washed with water and cold ethanol. Yellowish crystals suitable for X-ray analysis were obtained by recrystallization of the precipitate in DMSO.

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

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsods drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound viewed down the b axis. Intermolecular hydrogen bonds are shown as dashed lines.

1-(Biphenyl-4-ylcarbonyl)-3-(2-chloro-4-nitrophenyl)thiourea top

Crystal data top

C₂₀H₁₄ClN₃O₃S	F(000) = 848
M_r = 411.85	D_x = 1.529 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1235 reflections
a = 10.889 (2) Å	θ = 1.9–25.0°
b = 5.4502 (10) Å	µ = 0.36 mm⁻¹
c = 30.532 (5) Å	T = 298 K
β = 99.202 (4)°	Slab, yellow
V = 1788.6 (6) Å³	0.35 × 0.13 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3154 independent reflections
Radiation source: fine-focus sealed tube	2704 reflections with I > 2/s(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.0°, θ_min = 1.9°
ω scan	h = −11→12
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −6→6
T_min = 0.885, T_max = 0.972	l = −35→36
9537 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0709P)² + 0.5419P] where P = (F_o² + 2F_c²)/3
3154 reflections	(Δ/σ)_max = 0.002
253 parameters	Δρ_max = 0.25 e Å⁻³
3 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₀H₁₄ClN₃O₃S	V = 1788.6 (6) Å³
M_r = 411.85	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.889 (2) Å	µ = 0.36 mm⁻¹
b = 5.4502 (10) Å	T = 298 K
c = 30.532 (5) Å	0.35 × 0.13 × 0.08 mm
β = 99.202 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3154 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2704 reflections with I > 2/s(I)
T_min = 0.885, T_max = 0.972	R_int = 0.026
9537 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	3 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.16	Δρ_max = 0.25 e Å⁻³
3154 reflections	Δρ_min = −0.24 e Å⁻³
253 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	0.66457 (7)	0.06984 (14)	0.93137 (2)	0.0553 (3)
Cl1	0.88661 (6)	0.87141 (13)	1.03030 (2)	0.0511 (2)
O1	0.9472 (2)	0.6794 (4)	0.93384 (7)	0.0691 (7)
O2	0.5004 (3)	0.4603 (5)	1.13921 (9)	0.0849 (8)
O3	0.6132 (2)	0.7850 (5)	1.15220 (7)	0.0701 (6)
N1	0.8315 (2)	0.3541 (4)	0.90589 (7)	0.0449 (5)
H1A	0.8162	0.2613	0.8829	0.054*
N2	0.7806 (2)	0.4647 (4)	0.97322 (7)	0.0456 (5)
H2A	0.8366	0.5731	0.9709	0.055*
N3	0.5772 (2)	0.6060 (5)	1.12973 (9)	0.0559 (6)
C1	1.0767 (3)	0.7043 (5)	0.86344 (10)	0.0538 (7)
H1B	1.0856	0.8296	0.8844	0.065*
C2	1.1482 (3)	0.7078 (5)	0.83008 (9)	0.0509 (7)
H2B	1.2040	0.8359	0.8290	0.061*
C3	1.1390 (2)	0.5250 (5)	0.79806 (8)	0.0374 (6)
C4	1.0527 (3)	0.3419 (5)	0.80119 (9)	0.0520 (7)
H4A	1.0432	0.2171	0.7801	0.062*
C5	0.9802 (3)	0.3377 (5)	0.83435 (9)	0.0509 (7)
H5A	0.9228	0.2119	0.8351	0.061*
C6	0.9919 (2)	0.5184 (5)	0.86650 (8)	0.0394 (6)
C7	1.2173 (2)	0.5270 (5)	0.76232 (8)	0.0393 (6)
C8	1.3045 (3)	0.7076 (6)	0.75971 (10)	0.0609 (8)
H8A	1.3153	0.8315	0.7809	0.073*
C9	1.3767 (3)	0.7083 (7)	0.72601 (11)	0.0681 (9)
H9A	1.4342	0.8333	0.7248	0.082*
C10	1.3638 (3)	0.5275 (6)	0.69487 (9)	0.0551 (8)
H10A	1.4127	0.5274	0.6725	0.066*
C11	1.2787 (3)	0.3470 (7)	0.69684 (11)	0.0661 (9)
H11A	1.2691	0.2228	0.6757	0.079*
C12	1.2060 (3)	0.3469 (6)	0.73013 (10)	0.0570 (8)
H12A	1.1481	0.2222	0.7308	0.068*
C13	0.9227 (2)	0.5278 (5)	0.90462 (9)	0.0439 (6)
C14	0.7603 (2)	0.3068 (5)	0.93919 (8)	0.0404 (6)
C15	0.7273 (2)	0.4852 (5)	1.01169 (8)	0.0408 (6)
C16	0.6357 (3)	0.3307 (6)	1.02337 (10)	0.0543 (7)
H16A	0.6067	0.2002	1.0050	0.065*
C17	0.5876 (3)	0.3692 (6)	1.06191 (10)	0.0547 (7)
H17A	0.5274	0.2636	1.0696	0.066*
C18	0.6284 (2)	0.5623 (5)	1.08869 (9)	0.0446 (6)
C19	0.7191 (2)	0.7181 (5)	1.07878 (8)	0.0449 (6)
H19A	0.7467	0.8485	1.0974	0.054*
C20	0.7686 (2)	0.6773 (5)	1.04071 (8)	0.0396 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0593 (5)	0.0552 (5)	0.0514 (4)	−0.0271 (4)	0.0085 (3)	−0.0054 (3)
Cl1	0.0524 (4)	0.0538 (4)	0.0498 (4)	−0.0219 (3)	0.0157 (3)	−0.0058 (3)
O1	0.0819 (15)	0.0638 (14)	0.0722 (14)	−0.0380 (12)	0.0450 (12)	−0.0317 (12)
O2	0.0952 (18)	0.0893 (18)	0.0836 (16)	−0.0164 (13)	0.0550 (15)	0.0070 (14)
O3	0.0645 (14)	0.0899 (16)	0.0605 (13)	0.0008 (11)	0.0238 (11)	−0.0129 (12)
N1	0.0453 (12)	0.0477 (13)	0.0434 (12)	−0.0120 (10)	0.0128 (10)	−0.0082 (10)
N2	0.0458 (13)	0.0420 (12)	0.0526 (13)	−0.0151 (10)	0.0190 (10)	−0.0077 (11)
N3	0.0498 (14)	0.0645 (16)	0.0577 (14)	0.0066 (11)	0.0216 (11)	0.0093 (11)
C1	0.0617 (18)	0.0461 (17)	0.0583 (17)	−0.0176 (14)	0.0241 (14)	−0.0175 (14)
C2	0.0548 (17)	0.0448 (16)	0.0573 (17)	−0.0188 (13)	0.0219 (13)	−0.0077 (13)
C3	0.0366 (13)	0.0363 (13)	0.0390 (13)	0.0025 (10)	0.0051 (10)	0.0045 (11)
C4	0.0615 (18)	0.0478 (17)	0.0504 (16)	−0.0162 (14)	0.0201 (13)	−0.0125 (13)
C5	0.0573 (17)	0.0461 (16)	0.0534 (16)	−0.0211 (13)	0.0216 (13)	−0.0096 (13)
C6	0.0393 (13)	0.0382 (14)	0.0410 (13)	−0.0018 (11)	0.0076 (11)	0.0008 (11)
C7	0.0386 (13)	0.0429 (14)	0.0361 (12)	0.0016 (11)	0.0049 (10)	0.0066 (11)
C8	0.071 (2)	0.061 (2)	0.0552 (17)	−0.0232 (16)	0.0239 (15)	−0.0135 (15)
C9	0.073 (2)	0.075 (2)	0.0625 (19)	−0.0270 (18)	0.0315 (16)	−0.0033 (17)
C10	0.0517 (17)	0.072 (2)	0.0442 (15)	0.0002 (15)	0.0169 (13)	0.0032 (15)
C11	0.070 (2)	0.074 (2)	0.0601 (18)	−0.0131 (18)	0.0278 (16)	−0.0217 (17)
C12	0.0601 (18)	0.0551 (18)	0.0606 (17)	−0.0152 (14)	0.0240 (14)	−0.0149 (15)
C13	0.0427 (14)	0.0406 (15)	0.0500 (15)	−0.0056 (12)	0.0118 (12)	−0.0052 (13)
C14	0.0337 (13)	0.0414 (15)	0.0452 (14)	−0.0030 (11)	0.0036 (10)	0.0034 (12)
C15	0.0375 (14)	0.0404 (14)	0.0461 (14)	−0.0030 (11)	0.0113 (11)	0.0016 (12)
C16	0.0545 (17)	0.0507 (17)	0.0624 (18)	−0.0163 (14)	0.0236 (14)	−0.0086 (14)
C17	0.0513 (16)	0.0541 (18)	0.0645 (18)	−0.0134 (14)	0.0265 (14)	0.0032 (15)
C18	0.0389 (14)	0.0507 (16)	0.0463 (14)	0.0028 (12)	0.0133 (11)	0.0062 (13)
C19	0.0425 (14)	0.0482 (16)	0.0441 (14)	−0.0021 (12)	0.0078 (11)	0.0005 (12)
C20	0.0343 (13)	0.0416 (15)	0.0439 (13)	−0.0056 (11)	0.0097 (10)	0.0027 (11)

Geometric parameters (Å, º) top

S1—C14	1.653 (3)	C5—H5A	0.9300
Cl1—C20	1.733 (3)	C6—C13	1.485 (4)
O1—C13	1.214 (3)	C7—C8	1.379 (4)
O2—N3	1.221 (3)	C7—C12	1.380 (4)
O3—N3	1.221 (3)	C8—C9	1.391 (4)
N1—C13	1.377 (3)	C8—H8A	0.9300
N1—C14	1.397 (3)	C9—C10	1.361 (5)
N1—H1A	0.8600	C9—H9A	0.9300
N2—C14	1.340 (3)	C10—C11	1.360 (5)
N2—C15	1.395 (3)	C10—H10A	0.9300
N2—H2A	0.8600	C11—C12	1.384 (4)
N3—C18	1.470 (4)	C11—H11A	0.9300
C1—C2	1.377 (4)	C12—H12A	0.9300
C1—C6	1.384 (4)	C15—C16	1.395 (4)
C1—H1B	0.9300	C15—C20	1.398 (4)
C2—C3	1.388 (4)	C16—C17	1.378 (4)
C2—H2B	0.9300	C16—H16A	0.9300
C3—C4	1.385 (4)	C17—C18	1.363 (4)
C3—C7	1.488 (3)	C17—H17A	0.9300
C4—C5	1.380 (4)	C18—C19	1.373 (4)
C4—H4A	0.9300	C19—C20	1.375 (3)
C5—C6	1.382 (4)	C19—H19A	0.9300

C13—N1—C14	129.3 (2)	C8—C9—H9A	119.7
C13—N1—H1A	115.3	C11—C10—C9	119.2 (3)
C14—N1—H1A	115.3	C11—C10—H10A	120.4
C14—N2—C15	131.7 (2)	C9—C10—H10A	120.4
C14—N2—H2A	114.1	C10—C11—C12	120.4 (3)
C15—N2—H2A	114.1	C10—C11—H11A	119.8
O2—N3—O3	123.9 (3)	C12—C11—H11A	119.8
O2—N3—C18	117.7 (3)	C7—C12—C11	121.8 (3)
O3—N3—C18	118.5 (2)	C7—C12—H12A	119.1
C2—C1—C6	121.5 (3)	C11—C12—H12A	119.1
C2—C1—H1B	119.3	O1—C13—N1	121.5 (2)
C6—C1—H1B	119.3	O1—C13—C6	121.3 (2)
C1—C2—C3	121.7 (2)	N1—C13—C6	117.2 (2)
C1—C2—H2B	119.2	N2—C14—N1	113.8 (2)
C3—C2—H2B	119.2	N2—C14—S1	129.5 (2)
C4—C3—C2	116.2 (2)	N1—C14—S1	116.71 (19)
C4—C3—C7	122.0 (2)	C16—C15—N2	125.3 (2)
C2—C3—C7	121.8 (2)	C16—C15—C20	117.4 (2)
C5—C4—C3	122.5 (3)	N2—C15—C20	117.3 (2)
C5—C4—H4A	118.8	C17—C16—C15	120.7 (3)
C3—C4—H4A	118.8	C17—C16—H16A	119.6
C4—C5—C6	120.7 (2)	C15—C16—H16A	119.6
C4—C5—H5A	119.7	C18—C17—C16	119.9 (3)
C6—C5—H5A	119.7	C18—C17—H17A	120.1
C5—C6—C1	117.4 (2)	C16—C17—H17A	120.1
C5—C6—C13	125.5 (2)	C17—C18—C19	121.5 (3)
C1—C6—C13	117.1 (2)	C17—C18—N3	120.3 (3)
C8—C7—C12	116.7 (2)	C19—C18—N3	118.2 (3)
C8—C7—C3	121.9 (2)	C18—C19—C20	118.6 (3)
C12—C7—C3	121.4 (2)	C18—C19—H19A	120.7
C7—C8—C9	121.4 (3)	C20—C19—H19A	120.7
C7—C8—H8A	119.3	C19—C20—C15	121.8 (2)
C9—C8—H8A	119.3	C19—C20—Cl1	117.3 (2)
C10—C9—C8	120.5 (3)	C15—C20—Cl1	120.91 (19)
C10—C9—H9A	119.7

C6—C1—C2—C3	−0.2 (5)	C5—C6—C13—N1	−6.0 (4)
C1—C2—C3—C4	1.0 (4)	C1—C6—C13—N1	175.1 (3)
C1—C2—C3—C7	−179.3 (3)	C15—N2—C14—N1	178.0 (2)
C2—C3—C4—C5	−0.7 (4)	C15—N2—C14—S1	−1.8 (4)
C7—C3—C4—C5	179.6 (3)	C13—N1—C14—N2	4.2 (4)
C3—C4—C5—C6	−0.5 (5)	C13—N1—C14—S1	−175.9 (2)
C4—C5—C6—C1	1.3 (4)	C14—N2—C15—C16	0.8 (5)
C4—C5—C6—C13	−177.5 (3)	C14—N2—C15—C20	−178.8 (3)
C2—C1—C6—C5	−0.9 (5)	N2—C15—C16—C17	−179.0 (3)
C2—C1—C6—C13	178.0 (3)	C20—C15—C16—C17	0.6 (4)
C4—C3—C7—C8	−179.0 (3)	C15—C16—C17—C18	1.0 (5)
C2—C3—C7—C8	1.3 (4)	C16—C17—C18—C19	−1.6 (5)
C4—C3—C7—C12	0.9 (4)	C16—C17—C18—N3	179.6 (3)
C2—C3—C7—C12	−178.8 (3)	O2—N3—C18—C17	1.9 (4)
C12—C7—C8—C9	0.5 (5)	O3—N3—C18—C17	−177.8 (3)
C3—C7—C8—C9	−179.7 (3)	O2—N3—C18—C19	−176.9 (3)
C7—C8—C9—C10	−0.8 (6)	O3—N3—C18—C19	3.3 (4)
C8—C9—C10—C11	0.6 (5)	C17—C18—C19—C20	0.5 (4)
C9—C10—C11—C12	−0.1 (5)	N3—C18—C19—C20	179.3 (2)
C8—C7—C12—C11	0.0 (5)	C18—C19—C20—C15	1.2 (4)
C3—C7—C12—C11	−179.8 (3)	C18—C19—C20—Cl1	−177.9 (2)
C10—C11—C12—C7	−0.2 (5)	C16—C15—C20—C19	−1.7 (4)
C14—N1—C13—O1	−4.7 (5)	N2—C15—C20—C19	177.9 (2)
C14—N1—C13—C6	173.9 (2)	C16—C15—C20—Cl1	177.3 (2)
C5—C6—C13—O1	172.6 (3)	N2—C15—C20—Cl1	−3.1 (3)
C1—C6—C13—O1	−6.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1	0.86	2.43	2.938 (2)	118
N2—H2A···O1	0.86	1.87	2.608 (3)	143
C16—H16A···S1	0.93	2.53	3.208 (3)	130
C10—H10A···O3ⁱ	0.93	2.57	3.354 (4)	142
C17—H17A···S1ⁱⁱ	0.93	2.77	3.673 (3)	165

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄ClN₃O₃S
M_r	411.85
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.889 (2), 5.4502 (10), 30.532 (5)
β (°)	99.202 (4)
V (Å³)	1788.6 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.35 × 0.13 × 0.08

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.885, 0.972
No. of measured, independent and observed [I > 2/s(I)] reflections	9537, 3154, 2704
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.137, 1.16
No. of reflections	3154
No. of parameters	253
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.24

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1	0.86	2.43	2.938 (2)	118
N2—H2A···O1	0.86	1.87	2.608 (3)	143
C16—H16A···S1	0.93	2.53	3.208 (3)	130
C10—H10A···O3ⁱ	0.93	2.57	3.354 (4)	142
C17—H17A···S1ⁱⁱ	0.93	2.77	3.673 (3)	165

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

Acknowledgements

The authors thank the Ministry of Higher Education of Malaysia, Universiti Kebangsaan Malaysia and Universiti Malaysia Terengganu for research grant 59166.

References

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