N-(4-Chloro-butanoyl)-N'-(2-fluoro-phen-yl)thio-urea.

In the title compound, C(11)H(12)ClFN(2)OS, the asymmetric unit consists of two indenpendent mol-ecules. Both mol-ecules maintain a trans-cis configuration of the positions of the butanoyl and fluoro-phenyl groups with respect to the thiono group across their C-N bonds and are stabilized by classical intra-molecular N-H⋯O hydrogen bonds. In the crystal, inter-molecular N-H⋯O, C-H⋯S and N-H⋯S hydrogen bonds link the mol-ecules 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 = 274.75

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.138

S = 0.89

4501 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.30 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024743/rk2280sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811024743/rk2280Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H12ClFN2OS	F(000) = 1136
Mr = 274.75	Dx = 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

Bruker SMART APEX CCD area-detector diffractometer	4501 independent reflections
Radiation source: fine-focus sealed tube	2231 reflections with I > 2σ(I)
graphite	Rint = 0.119
Detector resolution: 83.66 pixels mm-1	θmax = 25.0°, θmin = 1.5°
ω scans	h = −17→16
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −12→12
Tmin = 0.803, Tmax = 0.969	l = −13→21
13771 measured reflections

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(Fo2) + (0.0451P)2] where P = (Fo2 + 2Fc2)/3
4501 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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···S2iv	0.97	2.74	3.691 (5)	168

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⋯S2iv	0.97	2.74	3.691 (5)	168

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .