N-[Eth-yl(2-hy-droxy-eth-yl)carbamo-thio-yl]-3-fluoro-benzamide.

In the title compound, C12H15FN2O2S, the mol-ecule adopts a cis configuration of the fluoro-benzoyl group with respect to the thiono group about their C-N bond. The dihedral angle between the fluoro-benzoyl group and the thio-urea N2CS fragment is 69.60 (11)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, mol-ecules form chains along the b-axis direction via O-H⋯S and C-H⋯O hydrogen bonds.

Related literature

For bond length data see: Allen et al. (1987 ▶). For a related structure, see: Yamin et al. (2014 ▶).

Experimental

Crystal data

C12H15FN2O2S

M = 270.32

Orthorhombic,

a = 6.0205 (3) Å

b = 12.9441 (6) Å

c = 17.1071 (9) Å

V = 1333.16 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.50 × 0.50 × 0.29 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.885, T max = 0.931

21708 measured reflections

3290 independent reflections

2864 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.086

S = 1.07

3290 reflections

168 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1378 Friedel pairs

Absolute structure parameter: −0.05 (8)

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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814008174/bq2395sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008174/bq2395Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008174/bq2395Isup3.cml

CCDC reference: 996752

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H15FN2O2S	F(000) = 568
Mr = 270.32	Dx = 1.347 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 11689 reflections
a = 6.0205 (3) Å	θ = 3.1–28.2°
b = 12.9441 (6) Å	µ = 0.25 mm−1
c = 17.1071 (9) Å	T = 296 K
V = 1333.16 (11) Å3	Block, colorless
Z = 4	0.50 × 0.50 × 0.29 mm

Bruker SMART APEX CCD area-detector diffractometer	3290 independent reflections
Radiation source: fine-focus sealed tube	2864 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω scans	θmax = 28.2°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→7
Tmin = 0.885, Tmax = 0.931	k = −17→16
21708 measured reflections	l = −21→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0367P)2 + 0.3143P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3290 reflections	Δρmax = 0.22 e Å−3
168 parameters	Δρmin = −0.18 e Å−3
1 restraint	Absolute structure: Flack (1983), 1378 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (8)

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.

	x	y	z	Uiso*/Ueq
F1	−0.5492 (2)	0.22048 (12)	0.06124 (8)	0.0690 (4)
S1	0.25957 (10)	0.08756 (4)	0.35274 (3)	0.05288 (15)
O1	0.2778 (3)	0.02641 (9)	0.17285 (8)	0.0537 (4)
O2	0.0320 (2)	0.39036 (10)	0.21034 (9)	0.0501 (3)
H2A	−0.053 (3)	0.4382 (14)	0.2024 (14)	0.067 (7)*
N1	0.1564 (2)	0.18174 (10)	0.21762 (8)	0.0369 (3)
H1A	0.0836	0.2359	0.2039	0.044*
N2	0.3727 (2)	0.27479 (10)	0.30261 (8)	0.0360 (3)
C1	−0.2089 (3)	0.16654 (13)	0.11163 (9)	0.0382 (4)
H1	−0.2228	0.2134	0.1526	0.046*
C2	−0.3693 (3)	0.15905 (16)	0.05543 (10)	0.0438 (4)
C3	−0.3574 (4)	0.09202 (19)	−0.00610 (11)	0.0556 (5)
H3	−0.4698	0.0890	−0.0433	0.067*
C4	−0.1751 (4)	0.02952 (18)	−0.01123 (13)	0.0625 (6)
H4	−0.1633	−0.0167	−0.0526	0.075*
C5	−0.0084 (4)	0.03385 (15)	0.04385 (11)	0.0497 (5)
H5	0.1148	−0.0091	0.0394	0.060*
C6	−0.0245 (3)	0.10242 (12)	0.10612 (10)	0.0341 (3)
C7	0.1516 (3)	0.09866 (12)	0.16784 (10)	0.0349 (3)
C8	0.2701 (3)	0.18551 (11)	0.28899 (10)	0.0348 (3)
C9	0.4712 (4)	0.29815 (16)	0.37932 (11)	0.0546 (5)
H9A	0.3884	0.2621	0.4196	0.066*
H9B	0.4587	0.3717	0.3893	0.066*
C10	0.7126 (4)	0.26688 (19)	0.38404 (16)	0.0765 (8)
H10A	0.7259	0.1941	0.3743	0.115*
H10B	0.7690	0.2823	0.4352	0.115*
H10C	0.7964	0.3044	0.3456	0.115*
C11	0.4091 (3)	0.35433 (13)	0.24232 (10)	0.0366 (4)
H11A	0.4176	0.3211	0.1916	0.044*
H11B	0.5505	0.3879	0.2520	0.044*
C12	0.2301 (4)	0.43491 (12)	0.24008 (11)	0.0447 (4)
H12A	0.2041	0.4615	0.2923	0.054*
H12B	0.2760	0.4919	0.2070	0.054*

	U11	U22	U33	U12	U13	U23
F1	0.0511 (7)	0.0961 (10)	0.0598 (7)	0.0225 (7)	−0.0128 (6)	−0.0004 (7)
S1	0.0634 (3)	0.0408 (2)	0.0544 (3)	−0.0138 (2)	−0.0199 (3)	0.0157 (2)
O1	0.0596 (9)	0.0393 (6)	0.0622 (8)	0.0182 (7)	−0.0127 (7)	−0.0037 (6)
O2	0.0487 (8)	0.0337 (7)	0.0677 (9)	0.0113 (6)	−0.0071 (7)	−0.0017 (6)
N1	0.0404 (8)	0.0252 (6)	0.0451 (8)	0.0027 (6)	−0.0149 (6)	0.0016 (6)
N2	0.0388 (8)	0.0307 (7)	0.0385 (7)	−0.0034 (6)	−0.0073 (6)	−0.0005 (6)
C1	0.0421 (10)	0.0422 (8)	0.0301 (7)	0.0018 (8)	−0.0015 (7)	−0.0009 (6)
C2	0.0367 (9)	0.0559 (11)	0.0389 (9)	0.0023 (8)	−0.0004 (8)	0.0067 (8)
C3	0.0562 (12)	0.0745 (14)	0.0360 (9)	−0.0134 (12)	−0.0118 (9)	0.0010 (10)
C4	0.0816 (17)	0.0612 (13)	0.0446 (11)	−0.0042 (13)	−0.0055 (11)	−0.0176 (10)
C5	0.0578 (12)	0.0452 (10)	0.0460 (11)	0.0046 (9)	−0.0001 (9)	−0.0088 (9)
C6	0.0377 (8)	0.0304 (8)	0.0343 (8)	−0.0033 (7)	−0.0008 (7)	0.0019 (6)
C7	0.0355 (8)	0.0278 (7)	0.0413 (9)	−0.0010 (7)	−0.0014 (7)	0.0033 (6)
C8	0.0304 (8)	0.0315 (7)	0.0427 (8)	0.0003 (7)	−0.0065 (7)	0.0005 (6)
C9	0.0727 (14)	0.0475 (11)	0.0437 (10)	−0.0147 (10)	−0.0170 (10)	−0.0025 (9)
C10	0.0724 (17)	0.0650 (14)	0.0920 (17)	−0.0156 (13)	−0.0453 (15)	0.0178 (13)
C11	0.0368 (9)	0.0304 (8)	0.0425 (9)	−0.0040 (7)	−0.0002 (7)	0.0001 (7)
C12	0.0554 (12)	0.0275 (7)	0.0512 (10)	0.0047 (9)	−0.0025 (10)	−0.0039 (7)

F1—C2	1.347 (2)	C4—C5	1.377 (3)
S1—C8	1.6736 (16)	C4—H4	0.9300
O1—C7	1.208 (2)	C5—C6	1.390 (2)
O2—C12	1.419 (2)	C5—H5	0.9300
O2—H2A	0.816 (10)	C6—C7	1.497 (2)
N1—C7	1.372 (2)	C9—C10	1.511 (3)
N1—C8	1.401 (2)	C9—H9A	0.9700
N1—H1A	0.8600	C9—H9B	0.9700
N2—C8	1.331 (2)	C10—H10A	0.9600
N2—C9	1.471 (2)	C10—H10B	0.9600
N2—C11	1.474 (2)	C10—H10C	0.9600
C1—C2	1.366 (2)	C11—C12	1.500 (3)
C1—C6	1.389 (2)	C11—H11A	0.9700
C1—H1	0.9300	C11—H11B	0.9700
C2—C3	1.366 (3)	C12—H12A	0.9700
C3—C4	1.366 (3)	C12—H12B	0.9700
C3—H3	0.9300
C12—O2—H2A	106.3 (18)	N2—C8—N1	114.19 (13)
C7—N1—C8	125.36 (13)	N2—C8—S1	124.15 (13)
C7—N1—H1A	117.3	N1—C8—S1	121.54 (12)
C8—N1—H1A	117.3	N2—C9—C10	112.35 (19)
C8—N2—C9	121.44 (15)	N2—C9—H9A	109.1
C8—N2—C11	123.58 (14)	C10—C9—H9A	109.1
C9—N2—C11	114.88 (14)	N2—C9—H9B	109.1
C2—C1—C6	118.34 (16)	C10—C9—H9B	109.1
C2—C1—H1	120.8	H9A—C9—H9B	107.9
C6—C1—H1	120.8	C9—C10—H10A	109.5
F1—C2—C3	118.29 (17)	C9—C10—H10B	109.5
F1—C2—C1	118.32 (16)	H10A—C10—H10B	109.5
C3—C2—C1	123.38 (18)	C9—C10—H10C	109.5
C2—C3—C4	117.89 (18)	H10A—C10—H10C	109.5
C2—C3—H3	121.1	H10B—C10—H10C	109.5
C4—C3—H3	121.1	N2—C11—C12	113.38 (15)
C3—C4—C5	121.14 (19)	N2—C11—H11A	108.9
C3—C4—H4	119.4	C12—C11—H11A	108.9
C5—C4—H4	119.4	N2—C11—H11B	108.9
C4—C5—C6	120.0 (2)	C12—C11—H11B	108.9
C4—C5—H5	120.0	H11A—C11—H11B	107.7
C6—C5—H5	120.0	O2—C12—C11	109.28 (13)
C1—C6—C5	119.29 (16)	O2—C12—H12A	109.8
C1—C6—C7	122.51 (15)	C11—C12—H12A	109.8
C5—C6—C7	118.06 (16)	O2—C12—H12B	109.8
O1—C7—N1	123.33 (15)	C11—C12—H12B	109.8
O1—C7—C6	121.38 (15)	H12A—C12—H12B	108.3
N1—C7—C6	115.29 (14)
C6—C1—C2—F1	179.31 (16)	C1—C6—C7—N1	−18.5 (2)
C6—C1—C2—C3	−0.2 (3)	C5—C6—C7—N1	165.87 (16)
F1—C2—C3—C4	−179.56 (19)	C9—N2—C8—N1	170.60 (17)
C1—C2—C3—C4	0.0 (3)	C11—N2—C8—N1	−13.3 (2)
C2—C3—C4—C5	0.0 (3)	C9—N2—C8—S1	−5.4 (3)
C3—C4—C5—C6	0.2 (3)	C11—N2—C8—S1	170.74 (13)
C2—C1—C6—C5	0.5 (2)	C7—N1—C8—N2	139.06 (17)
C2—C1—C6—C7	−175.11 (16)	C7—N1—C8—S1	−44.8 (2)
C4—C5—C6—C1	−0.5 (3)	C8—N2—C9—C10	91.8 (2)
C4—C5—C6—C7	175.31 (19)	C11—N2—C9—C10	−84.6 (2)
C8—N1—C7—O1	−14.3 (3)	C8—N2—C11—C12	93.48 (19)
C8—N1—C7—C6	165.10 (16)	C9—N2—C11—C12	−90.17 (19)
C1—C6—C7—O1	160.93 (17)	N2—C11—C12—O2	−70.51 (19)
C5—C6—C7—O1	−14.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	2.03	2.805 (2)	150
C9—H9A···S1	0.97	2.65	3.043 (3)	105
O2—H2A···S1i	0.82 (3)	2.49 (3)	3.2805 (19)	166 (3)
C11—H11B···O1ii	0.97	2.44	3.259 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.86	2.03	2.805 (2)	150
O2—H2A⋯S1i	0.82 (3)	2.49 (3)	3.2805 (19)	166 (3)
C11—H11B⋯O1ii	0.97	2.44	3.259 (3)	142

Symmetry codes: (i) ; (ii) .