N-(4-Chloro­butanoyl)-N′-(2-fluoro­phen­yl)thio­urea

Yusof, M.S.M.; Embong, N.F.; Othman, E.A.; Yamin, B.M.

doi:10.1107/S1600536811024743

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1849

doi:10.1107/S1600536811024743

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N-(4-Chlorobutanoyl)-N′-(2-fluorophenyl)thiourea

M. Sukeri M. Yusof,^a ^* Nur Farhana Embong,^a Eliyanti A. Othman ^b 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 6 June 2011; accepted 23 June 2011; online 30 June 2011)

In the title compound, C₁₁H₁₂ClFN₂OS, the asymmetric unit consists of two indenpendent molecules. Both molecules maintain a trans–cis configuration of the positions of the butanoyl and fluorophenyl groups with respect to the thiono group across their C—N bonds and are stabilized by classical intramolecular N—H⋯O hydrogen bonds. In the crystal, intermolecular N—H⋯O, C—H⋯S and N—H⋯S hydrogen bonds link the molecules into infinite chains along the c axis.

Related literature

For a related structure, see: Yamin et al. (2011 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₂ClFN₂OS
M_r = 274.75
Monoclinic, P 2₁ /c
a = 14.818 (7) Å
b = 10.291 (5) Å
c = 18.201 (9) Å
β = 112.599 (12)°
V = 2562 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 298 K
0.50 × 0.22 × 0.07 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.803, T_max = 0.969
13771 measured reflections
4501 independent reflections
2231 reflections with I > 2σ(I)
R_int = 0.119

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.138
S = 0.89
4501 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.30 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	2.02	2.691 (5)	134
N2—H2⋯O2ⁱ	0.86	2.40	3.128 (5)	143
N4—H4⋯O2	0.86	2.02	2.676 (5)	133
N4—H4⋯O1ⁱⁱ	0.86	2.32	3.033 (5)	141
N3—H3⋯S1ⁱⁱⁱ	0.86	2.59	3.447 (4)	176
N1—H1⋯S2ⁱⁱⁱ	0.86	2.52	3.364 (4)	169
C14—H14A⋯S1ⁱⁱⁱ	0.97	2.96	3.784 (5)	143
C14—H14B⋯S2^iv	0.97	2.74	3.691 (5)	168
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z; (iv) -x, -y+2, -z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; 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/S1600536811024743/rk2280sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024743/rk2280Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024743/rk2280Isup3.cml

checkCIF report

Comment top

The title compound, is analogous to the previously reported N-(4-chlorobutanoyl)-N'-(phenyl)thiourea (Yamin et al., 2011) except the fluoro atom is attached at the ortho-position of the phenyl ring. The asymmetric unit consists of two independent molecules (Fig. 1). The whole molecule is not planar. However, the thiourea N1/C5/S1/N2/C6, N3/C16/S2/N4/C17 fragments and the benzene rings, (C6–C11) and (C17–C22) are each planar with maximum deviation of 0.020 (3)Å for N4 atom from the least square plane. In each molecule, the benzene ring and thiourea moiety forms dihedral angle of 74.78 (19)° and 82.3 (2)°, respectively. The same dihedral angle in N-(4-chlorobutanoyl)-N'-(phenyl)thiourea are 72.98 (12)° and 81.47 (14)°, respectively. The bond lengths and angles are in normal ranges (Allen et al., 1987) and comparable to those in the analog. Both molecules maintain their trans–cis-configuration with respect to the position of the butanoyl and fluorophenyl groups against the thiono C═S-group bond across the C—N bonds. Like in most of the carbonylthiourea derivatives, the classical intramolecular hydrogen bonds between the carbonyl oxygen atom and thioamide hydrogen atom, N2—H2···O1 and N4—H4···O2, in both molecules are present. In the crystal packing, the molecules are linked by N3—H3···S1ⁱⁱⁱ and N1—H1···S2ⁱⁱⁱ; N2—H2···O2ⁱ and N4—H4···O1ⁱⁱ; C14—H14A···S1ⁱⁱⁱ and C14—H14B···S2^iv intermolecular hydrogen bonds (symmetry codes as in Table 1) and form infinite chains along the c-axis (Fig. 2).

Related literature top

For a related structure, see: Yamin et al. (2011). For standard bond lengths, see: Allen et al. (1987).

Experimental top

A solution of 4-chlorobutanoylisothiocyanate (1.25 g, 6.33 mmol) in 30 ml acetone was added into a flask containing 30 ml acetone solution of 2-floroaniline (0.71 g, 6.33 mmol. The mixture was refluxed for 1 h. Then, the solution was filtered-off and left to evaporate at room temperature. The colourless solid was obtained after one day of evaporation (yield 83%, m.p. 411.7 K–415.5 K)

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius. intramolecular H bonds are presented by dashed lines.
	Fig. 2. A packing diagram of title compound viewed down the a-axis. H bonds are shown by dashed lines.

N-(4-Chlorobutanoyl)-N'-(2-fluorophenyl)thiourea top

Crystal data top

C₁₁H₁₂ClFN₂OS	F(000) = 1136
M_r = 274.75	D_x = 1.425 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 411.7–415.5 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.818 (7) Å	Cell parameters from 1404 reflections
b = 10.291 (5) Å	θ = 1.5–25.0°
c = 18.201 (9) Å	µ = 0.46 mm⁻¹
β = 112.599 (12)°	T = 298 K
V = 2562 (2) Å³	Plate, colourless
Z = 8	0.50 × 0.22 × 0.07 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4501 independent reflections
Radiation source: fine-focus sealed tube	2231 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.119
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.0°, θ_min = 1.5°
ω scans	h = −17→16
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −12→12
T_min = 0.803, T_max = 0.969	l = −13→21
13771 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 0.89	w = 1/[σ²(F_o²) + (0.0451P)²] where P = (F_o² + 2F_c²)/3
4501 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₁H₁₂ClFN₂OS	V = 2562 (2) Å³
M_r = 274.75	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.818 (7) Å	µ = 0.46 mm⁻¹
b = 10.291 (5) Å	T = 298 K
c = 18.201 (9) Å	0.50 × 0.22 × 0.07 mm
β = 112.599 (12)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4501 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2231 reflections with I > 2σ(I)
T_min = 0.803, T_max = 0.969	R_int = 0.119
13771 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 0.89	Δρ_max = 0.34 e Å⁻³
4501 reflections	Δρ_min = −0.30 e Å⁻³
307 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Cl1	0.49078 (11)	0.21242 (19)	0.00799 (10)	0.1269 (7)
F1	1.0669 (2)	−0.1688 (3)	0.35144 (16)	0.0795 (9)
F2	0.3894 (2)	0.7354 (3)	0.12270 (17)	0.0868 (9)
S1	1.02276 (8)	−0.03047 (12)	0.17159 (6)	0.0509 (3)
S2	0.24427 (8)	1.01331 (12)	0.02342 (6)	0.0502 (3)
Cl2	−0.23288 (9)	0.68710 (13)	−0.21630 (7)	0.0804 (5)
O1	0.80228 (19)	0.1449 (3)	0.26210 (18)	0.0562 (9)
O2	0.0637 (2)	0.6917 (3)	0.07106 (17)	0.0552 (9)
N1	0.8543 (2)	0.0465 (3)	0.17333 (18)	0.0424 (9)
H1	0.8335	0.0212	0.1246	0.051*
N2	0.9869 (2)	0.0693 (3)	0.29214 (19)	0.0428 (9)
H2	0.9467	0.1033	0.3103	0.051*
N3	0.0918 (2)	0.8641 (3)	0.00426 (18)	0.0421 (9)
H3	0.0658	0.9086	−0.0388	0.051*
N4	0.2217 (2)	0.8449 (3)	0.12431 (18)	0.0447 (9)
H4	0.1883	0.7860	0.1360	0.054*
C1	0.5036 (3)	0.1269 (6)	0.0958 (3)	0.0858 (19)
H1A	0.4571	0.1608	0.1167	0.103*
H1B	0.4885	0.0359	0.0831	0.103*
C2	0.6047 (3)	0.1386 (5)	0.1580 (3)	0.0718 (16)
H2A	0.6195	0.2299	0.1700	0.086*
H2B	0.6065	0.0966	0.2063	0.086*
C3	0.6818 (3)	0.0806 (5)	0.1350 (2)	0.0547 (13)
H3A	0.6790	0.1208	0.0860	0.066*
H3B	0.6682	−0.0113	0.1246	0.066*
C4	0.7839 (3)	0.0961 (4)	0.1974 (3)	0.0453 (11)
C5	0.9539 (3)	0.0312 (4)	0.2162 (2)	0.0410 (11)
C6	1.0875 (3)	0.0553 (4)	0.3442 (2)	0.0407 (11)
C7	1.1249 (3)	−0.0633 (5)	0.3737 (3)	0.0522 (12)
C8	1.2206 (4)	−0.0794 (6)	0.4252 (3)	0.0739 (16)
H8	1.2448	−0.1613	0.4445	0.089*
C9	1.2793 (4)	0.0285 (7)	0.4472 (3)	0.0822 (19)
H9	1.3443	0.0198	0.4816	0.099*
C10	1.2431 (3)	0.1484 (6)	0.4192 (3)	0.0786 (17)
H10	1.2835	0.2210	0.4346	0.094*
C11	1.1459 (3)	0.1625 (5)	0.3675 (3)	0.0610 (14)
H11	1.1209	0.2444	0.3489	0.073*
C12	−0.2143 (3)	0.6210 (5)	−0.1206 (3)	0.0691 (15)
H12A	−0.2532	0.6696	−0.0977	0.083*
H12B	−0.2369	0.5316	−0.1269	0.083*
C13	−0.1093 (3)	0.6249 (4)	−0.0646 (2)	0.0530 (13)
H13A	−0.0713	0.5723	−0.0865	0.064*
H13B	−0.1036	0.5862	−0.0145	0.064*
C14	−0.0659 (3)	0.7590 (4)	−0.0487 (2)	0.0490 (12)
H14A	−0.0639	0.7934	−0.0977	0.059*
H14B	−0.1086	0.8147	−0.0334	0.059*
C15	0.0351 (3)	0.7652 (4)	0.0149 (2)	0.0418 (11)
C16	0.1846 (3)	0.9006 (4)	0.0537 (2)	0.0386 (10)
C17	0.3156 (3)	0.8794 (4)	0.1821 (2)	0.0453 (12)
C18	0.3983 (3)	0.8244 (5)	0.1795 (3)	0.0566 (13)
C19	0.4902 (3)	0.8541 (6)	0.2342 (3)	0.0781 (17)
H19	0.5457	0.8151	0.2319	0.094*
C20	0.4970 (4)	0.9431 (7)	0.2921 (4)	0.091 (2)
H20	0.5584	0.9657	0.3291	0.109*
C21	0.4160 (4)	0.9992 (5)	0.2966 (3)	0.0777 (17)
H21	0.4221	1.0588	0.3366	0.093*
C22	0.3243 (3)	0.9664 (4)	0.2409 (3)	0.0571 (13)
H22	0.2686	1.0039	0.2438	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0706 (11)	0.1612 (18)	0.1063 (14)	0.0426 (11)	−0.0131 (9)	0.0101 (12)
F1	0.077 (2)	0.0548 (19)	0.098 (2)	0.0034 (15)	0.0232 (16)	0.0093 (16)
F2	0.068 (2)	0.111 (3)	0.081 (2)	0.0213 (17)	0.0283 (16)	−0.0051 (19)
S1	0.0373 (6)	0.0695 (9)	0.0458 (7)	0.0083 (6)	0.0157 (5)	−0.0007 (6)
S2	0.0383 (6)	0.0665 (9)	0.0432 (7)	−0.0099 (6)	0.0128 (5)	0.0030 (6)
Cl2	0.0695 (9)	0.0838 (10)	0.0632 (9)	−0.0010 (7)	−0.0020 (7)	−0.0005 (7)
O1	0.0393 (18)	0.072 (2)	0.051 (2)	0.0063 (15)	0.0105 (15)	−0.0195 (17)
O2	0.0491 (19)	0.050 (2)	0.053 (2)	−0.0104 (15)	0.0043 (15)	0.0103 (16)
N1	0.0292 (19)	0.059 (2)	0.035 (2)	0.0022 (17)	0.0072 (16)	−0.0047 (16)
N2	0.0299 (19)	0.052 (2)	0.041 (2)	0.0042 (16)	0.0075 (16)	−0.0039 (17)
N3	0.032 (2)	0.052 (2)	0.036 (2)	−0.0023 (17)	0.0056 (16)	0.0003 (16)
N4	0.031 (2)	0.054 (2)	0.043 (2)	−0.0076 (16)	0.0067 (16)	0.0077 (17)
C1	0.030 (3)	0.135 (5)	0.086 (4)	−0.007 (3)	0.014 (3)	−0.035 (4)
C2	0.037 (3)	0.110 (5)	0.065 (3)	−0.002 (3)	0.017 (2)	−0.014 (3)
C3	0.031 (2)	0.078 (4)	0.051 (3)	0.006 (2)	0.011 (2)	−0.003 (2)
C4	0.037 (3)	0.051 (3)	0.045 (3)	0.003 (2)	0.013 (2)	−0.001 (2)
C5	0.033 (2)	0.040 (3)	0.045 (3)	−0.0013 (19)	0.009 (2)	0.003 (2)
C6	0.032 (2)	0.053 (3)	0.033 (2)	0.004 (2)	0.0073 (18)	−0.004 (2)
C7	0.046 (3)	0.055 (3)	0.051 (3)	0.007 (3)	0.013 (2)	−0.002 (2)
C8	0.058 (4)	0.089 (4)	0.061 (3)	0.032 (3)	0.007 (3)	0.008 (3)
C9	0.034 (3)	0.133 (6)	0.063 (4)	0.022 (3)	0.001 (3)	−0.007 (4)
C10	0.036 (3)	0.100 (5)	0.089 (4)	−0.013 (3)	0.011 (3)	−0.026 (3)
C11	0.047 (3)	0.055 (3)	0.070 (3)	0.003 (2)	0.010 (2)	−0.007 (3)
C12	0.050 (3)	0.082 (4)	0.068 (3)	−0.022 (3)	0.015 (3)	−0.010 (3)
C13	0.046 (3)	0.059 (3)	0.048 (3)	−0.012 (2)	0.011 (2)	−0.004 (2)
C14	0.032 (2)	0.052 (3)	0.060 (3)	0.003 (2)	0.014 (2)	−0.004 (2)
C15	0.032 (2)	0.042 (3)	0.045 (3)	0.000 (2)	0.008 (2)	−0.007 (2)
C16	0.028 (2)	0.048 (3)	0.038 (3)	−0.0008 (19)	0.0109 (19)	−0.003 (2)
C17	0.031 (3)	0.053 (3)	0.043 (3)	−0.005 (2)	0.005 (2)	0.010 (2)
C18	0.045 (3)	0.069 (4)	0.053 (3)	0.000 (3)	0.016 (2)	0.005 (3)
C19	0.037 (3)	0.104 (5)	0.082 (4)	0.006 (3)	0.011 (3)	0.025 (4)
C20	0.047 (4)	0.105 (5)	0.089 (5)	−0.022 (4)	−0.007 (3)	0.022 (4)
C21	0.068 (4)	0.077 (4)	0.068 (4)	−0.016 (3)	0.005 (3)	−0.013 (3)
C22	0.050 (3)	0.053 (3)	0.058 (3)	0.001 (2)	0.009 (2)	0.000 (3)

Geometric parameters (Å, º) top

Cl1—C1	1.769 (6)	C6—C7	1.361 (6)
F1—C7	1.347 (5)	C6—C11	1.365 (5)
F2—C18	1.350 (5)	C7—C8	1.377 (6)
S1—C5	1.654 (4)	C8—C9	1.372 (7)
S2—C16	1.675 (4)	C8—H8	0.9300
Cl2—C12	1.791 (5)	C9—C10	1.364 (7)
O1—C4	1.212 (4)	C9—H9	0.9300
O2—C15	1.210 (4)	C10—C11	1.393 (6)
N1—C4	1.374 (5)	C10—H10	0.9300
N1—C5	1.388 (4)	C11—H11	0.9300
N1—H1	0.8600	C12—C13	1.498 (5)
N2—C5	1.336 (5)	C12—H12A	0.9700
N2—C6	1.433 (5)	C12—H12B	0.9700
N2—H2	0.8600	C13—C14	1.502 (5)
N3—C16	1.375 (4)	C13—H13A	0.9700
N3—C15	1.380 (5)	C13—H13B	0.9700
N3—H3	0.8600	C14—C15	1.501 (5)
N4—C16	1.318 (4)	C14—H14A	0.9700
N4—C17	1.430 (5)	C14—H14B	0.9700
N4—H4	0.8600	C17—C22	1.363 (6)
C1—C2	1.496 (5)	C17—C18	1.366 (6)
C1—H1A	0.9700	C18—C19	1.377 (6)
C1—H1B	0.9700	C19—C20	1.369 (7)
C2—C3	1.485 (6)	C19—H19	0.9300
C2—H2A	0.9700	C20—C21	1.363 (8)
C2—H2B	0.9700	C20—H20	0.9300
C3—C4	1.511 (5)	C21—C22	1.389 (6)
C3—H3A	0.9700	C21—H21	0.9300
C3—H3B	0.9700	C22—H22	0.9300

C4—N1—C5	129.5 (4)	C9—C10—C11	120.2 (5)
C4—N1—H1	115.2	C9—C10—H10	119.9
C5—N1—H1	115.2	C11—C10—H10	119.9
C5—N2—C6	121.9 (4)	C6—C11—C10	119.5 (5)
C5—N2—H2	119.0	C6—C11—H11	120.2
C6—N2—H2	119.0	C10—C11—H11	120.2
C16—N3—C15	128.2 (3)	C13—C12—Cl2	112.4 (4)
C16—N3—H3	115.9	C13—C12—H12A	109.1
C15—N3—H3	115.9	Cl2—C12—H12A	109.1
C16—N4—C17	122.1 (3)	C13—C12—H12B	109.1
C16—N4—H4	118.9	Cl2—C12—H12B	109.1
C17—N4—H4	118.9	H12A—C12—H12B	107.8
C2—C1—Cl1	111.9 (4)	C12—C13—C14	114.3 (4)
C2—C1—H1A	109.2	C12—C13—H13A	108.7
Cl1—C1—H1A	109.2	C14—C13—H13A	108.7
C2—C1—H1B	109.2	C12—C13—H13B	108.7
Cl1—C1—H1B	109.2	C14—C13—H13B	108.7
H1A—C1—H1B	107.9	H13A—C13—H13B	107.6
C3—C2—C1	114.2 (4)	C15—C14—C13	114.4 (3)
C3—C2—H2A	108.7	C15—C14—H14A	108.7
C1—C2—H2A	108.7	C13—C14—H14A	108.7
C3—C2—H2B	108.7	C15—C14—H14B	108.7
C1—C2—H2B	108.7	C13—C14—H14B	108.7
H2A—C2—H2B	107.6	H14A—C14—H14B	107.6
C2—C3—C4	113.7 (4)	O2—C15—N3	123.0 (4)
C2—C3—H3A	108.8	O2—C15—C14	123.2 (4)
C4—C3—H3A	108.8	N3—C15—C14	113.8 (4)
C2—C3—H3B	108.8	N4—C16—N3	117.2 (4)
C4—C3—H3B	108.8	N4—C16—S2	123.2 (3)
H3A—C3—H3B	107.7	N3—C16—S2	119.7 (3)
O1—C4—N1	123.3 (4)	C22—C17—C18	119.0 (4)
O1—C4—C3	124.0 (4)	C22—C17—N4	120.8 (4)
N1—C4—C3	112.6 (4)	C18—C17—N4	120.3 (4)
N2—C5—N1	115.8 (4)	F2—C18—C17	118.9 (4)
N2—C5—S1	124.8 (3)	F2—C18—C19	118.9 (5)
N1—C5—S1	119.4 (3)	C17—C18—C19	122.2 (5)
C7—C6—C11	119.3 (4)	C20—C19—C18	117.7 (5)
C7—C6—N2	120.9 (4)	C20—C19—H19	121.2
C11—C6—N2	119.8 (4)	C18—C19—H19	121.2
F1—C7—C6	119.2 (4)	C21—C20—C19	121.6 (5)
F1—C7—C8	118.6 (5)	C21—C20—H20	119.2
C6—C7—C8	122.2 (5)	C19—C20—H20	119.2
C9—C8—C7	118.2 (5)	C20—C21—C22	119.4 (5)
C9—C8—H8	120.9	C20—C21—H21	120.3
C7—C8—H8	120.9	C22—C21—H21	120.3
C10—C9—C8	120.6 (5)	C17—C22—C21	120.2 (5)
C10—C9—H9	119.7	C17—C22—H22	119.9
C8—C9—H9	119.7	C21—C22—H22	119.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	2.02	2.691 (5)	134
N2—H2···O2ⁱ	0.86	2.40	3.128 (5)	143
N4—H4···O2	0.86	2.02	2.676 (5)	133
N4—H4···O1ⁱⁱ	0.86	2.32	3.033 (5)	141
N3—H3···S1ⁱⁱⁱ	0.86	2.59	3.447 (4)	176
N1—H1···S2ⁱⁱⁱ	0.86	2.52	3.364 (4)	169
C3—H3A···Cl1	0.97	2.76	3.189 (5)	107
C14—H14A···Cl2	0.97	2.82	3.190 (4)	103
C14—H14A···S1ⁱⁱⁱ	0.97	2.96	3.784 (5)	143
C14—H14B···S2^iv	0.97	2.74	3.691 (5)	168

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂ClFN₂OS
M_r	274.75
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	14.818 (7), 10.291 (5), 18.201 (9)
β (°)	112.599 (12)
V (Å³)	2562 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.50 × 0.22 × 0.07

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.803, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	13771, 4501, 2231
R_int	0.119
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.138, 0.89
No. of reflections	4501
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.30

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), 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—H2···O1	0.86	2.02	2.691 (5)	134
N2—H2···O2ⁱ	0.86	2.40	3.128 (5)	143
N4—H4···O2	0.86	2.02	2.676 (5)	133
N4—H4···O1ⁱⁱ	0.86	2.32	3.033 (5)	141
N3—H3···S1ⁱⁱⁱ	0.86	2.59	3.447 (4)	176
N1—H1···S2ⁱⁱⁱ	0.86	2.52	3.364 (4)	169
C3—H3A···Cl1	0.97	2.76	3.189 (5)	107
C14—H14A···Cl2	0.97	2.82	3.190 (4)	103
C14—H14A···S1ⁱⁱⁱ	0.97	2.96	3.784 (5)	143
C14—H14B···S2^iv	0.97	2.74	3.691 (5)	168

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

Acknowledgements

The authors thank the Malaysian Government, Universiti Kebangsaan Malaysia, Universiti Malaysia Terengganu and the Ministry of Higher Education, Malaysia, for research grants UKM–GUP–NBT–08–27–110 and FRGS 59178.

References

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