1-(2-Fluoro-phen-yl)-3-(3,4,5-trimethoxy-benzo-yl)thio-urea.

The two m-meth-oxy groups of the title compound, C(17)H(17)FN(2)O(4)S, are almost coplanar with the aromatic ring [CH(3)-O-C-C = 5.8 (1) and 5.9 (1)°], whereas the meth-oxy group in the para position is bent out of the ring plane [78.6 (1)°]. Mol-ecules are connected by inter-molecular N-H⋯S hydrogen bonds to form centrosymmetric dimers that are stacked along the a axis.

Related literature

For details of the biological activity of fluorinated thio­ureas, see: Sun et al. (2006 ▶); Saeed et al. (2009 ▶); Xu et al. (2003 ▶). For the use of fluorinated thio­ureas in organic synthesis, see: Nosova et al. (2006 ▶, 2007 ▶); Berkessel et al. (2006 ▶). For fluorine-containing heterocycles, see: Lipunova et al. (2008 ▶). For intra­molecular hydrogen bonds and Fermi resonance measurements, see: Hritzová & Koščík (2008 ▶).

Experimental

Crystal data

C17H17FN2O4S

M = 364.39

Triclinic,

a = 4.0828 (5) Å

b = 14.0420 (16) Å

c = 14.2295 (16) Å

α = 91.092 (2)°

β = 90.694 (2)°

γ = 91.712 (2)°

V = 815.21 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 120 K

0.48 × 0.20 × 0.19 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.896, T max = 0.957

7686 measured reflections

3868 independent reflections

3128 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.109

S = 1.03

3868 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681001408X/si2257sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001408X/si2257Isup2.hkl

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

C17H17FN2O4S	Z = 2
Mr = 364.39	F(000) = 380
Triclinic, P1	Dx = 1.484 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.0828 (5) Å	Cell parameters from 2067 reflections
b = 14.0420 (16) Å	θ = 2.9–28.2°
c = 14.2295 (16) Å	µ = 0.24 mm−1
α = 91.092 (2)°	T = 120 K
β = 90.694 (2)°	Prism, colourless
γ = 91.712 (2)°	0.48 × 0.20 × 0.19 mm
V = 815.21 (16) Å3

Bruker SMART APEX diffractometer	3868 independent reflections
Radiation source: sealed tube	3128 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 27.9°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −5→5
Tmin = 0.896, Tmax = 0.957	k = −18→18
7686 measured reflections	l = −17→18

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)] = 0.042	Hydrogen site location: difference Fourier map
wR(F2) = 0.109	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0485P)2 + 0.2731P] where P = (Fo2 + 2Fc2)/3
3868 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
S1	0.28840 (12)	0.51052 (3)	0.37700 (3)	0.02191 (13)
F1	0.1367 (3)	0.83707 (8)	0.21822 (8)	0.0346 (3)
O1	0.0156 (4)	0.81511 (9)	0.44315 (9)	0.0287 (3)
O2	−0.5433 (3)	0.95757 (8)	0.72291 (8)	0.0239 (3)
O3	−0.3506 (3)	0.85284 (8)	0.86784 (8)	0.0220 (3)
O4	0.0054 (3)	0.70067 (8)	0.84415 (8)	0.0228 (3)
N1	0.2791 (4)	0.69556 (10)	0.32920 (10)	0.0220 (3)
H1A	0.2360	0.7532	0.3500	0.026*
N2	0.0880 (4)	0.65816 (10)	0.47587 (10)	0.0199 (3)
H2A	0.0559	0.6148	0.5189	0.024*
C1	0.3979 (4)	0.69150 (12)	0.23660 (12)	0.0199 (4)
C2	0.5894 (5)	0.62118 (13)	0.19798 (13)	0.0264 (4)
H2B	0.6512	0.5687	0.2347	0.032*
C3	0.6906 (5)	0.62772 (13)	0.10527 (14)	0.0309 (5)
H3A	0.8210	0.5792	0.0791	0.037*
C4	0.6043 (5)	0.70389 (13)	0.05025 (13)	0.0279 (4)
H4A	0.6729	0.7071	−0.0132	0.033*
C5	0.4183 (5)	0.77486 (13)	0.08855 (13)	0.0271 (4)
H5A	0.3590	0.8279	0.0522	0.032*
C6	0.3206 (5)	0.76752 (12)	0.17987 (13)	0.0232 (4)
C7	0.2210 (4)	0.62634 (12)	0.39079 (11)	0.0176 (3)
C8	0.0018 (4)	0.74974 (11)	0.49981 (12)	0.0190 (3)
C9	−0.1053 (4)	0.76904 (11)	0.59750 (11)	0.0174 (3)
C10	−0.2858 (4)	0.85088 (11)	0.61089 (12)	0.0189 (3)
H10A	−0.3518	0.8868	0.5584	0.023*
C11	−0.3685 (4)	0.87953 (11)	0.70090 (12)	0.0187 (3)
C12	−0.2668 (4)	0.82639 (11)	0.77787 (11)	0.0182 (3)
C13	−0.0860 (4)	0.74466 (11)	0.76356 (11)	0.0175 (3)
C14	−0.0055 (4)	0.71485 (11)	0.67339 (12)	0.0181 (3)
H14A	0.1150	0.6588	0.6635	0.022*
C15	−0.6232 (5)	1.01977 (12)	0.64767 (13)	0.0262 (4)
H15A	−0.7484	1.0730	0.6723	0.039*
H15B	−0.7549	0.9843	0.5999	0.039*
H15C	−0.4210	1.0444	0.6194	0.039*
C16	−0.1525 (5)	0.93050 (14)	0.90583 (13)	0.0296 (4)
H16A	−0.2241	0.9460	0.9697	0.044*
H16B	−0.1753	0.9863	0.8662	0.044*
H16C	0.0774	0.9124	0.9077	0.044*
C17	0.1706 (5)	0.61312 (12)	0.83456 (13)	0.0247 (4)
H17B	0.2231	0.5891	0.8970	0.037*
H17C	0.3735	0.6237	0.7996	0.037*
H17D	0.0289	0.5663	0.8004	0.037*

	U11	U22	U33	U12	U13	U23
S1	0.0321 (3)	0.0160 (2)	0.0179 (2)	0.00099 (17)	0.00664 (18)	0.00108 (16)
F1	0.0514 (8)	0.0262 (6)	0.0278 (6)	0.0146 (5)	0.0146 (5)	0.0083 (5)
O1	0.0488 (9)	0.0200 (6)	0.0181 (6)	0.0067 (6)	0.0106 (6)	0.0048 (5)
O2	0.0307 (7)	0.0210 (6)	0.0207 (6)	0.0083 (5)	0.0058 (5)	0.0027 (5)
O3	0.0309 (7)	0.0197 (6)	0.0152 (6)	−0.0016 (5)	0.0066 (5)	−0.0027 (5)
O4	0.0358 (8)	0.0189 (6)	0.0139 (6)	0.0060 (5)	0.0014 (5)	0.0024 (5)
N1	0.0360 (9)	0.0155 (7)	0.0147 (7)	0.0027 (6)	0.0068 (6)	0.0006 (5)
N2	0.0310 (9)	0.0165 (7)	0.0123 (7)	0.0005 (6)	0.0037 (6)	0.0016 (5)
C1	0.0266 (10)	0.0195 (8)	0.0135 (8)	−0.0010 (7)	0.0035 (7)	0.0018 (6)
C2	0.0348 (11)	0.0218 (9)	0.0233 (9)	0.0045 (8)	0.0084 (8)	0.0050 (7)
C3	0.0431 (12)	0.0252 (9)	0.0250 (10)	0.0035 (8)	0.0141 (9)	−0.0003 (8)
C4	0.0388 (12)	0.0298 (10)	0.0150 (8)	−0.0035 (8)	0.0076 (8)	0.0017 (7)
C5	0.0339 (11)	0.0277 (9)	0.0199 (9)	−0.0004 (8)	0.0022 (8)	0.0091 (7)
C6	0.0281 (10)	0.0208 (8)	0.0209 (9)	0.0028 (7)	0.0047 (7)	0.0004 (7)
C7	0.0211 (9)	0.0196 (8)	0.0122 (8)	−0.0004 (6)	0.0017 (6)	−0.0002 (6)
C8	0.0241 (9)	0.0174 (8)	0.0156 (8)	0.0001 (6)	0.0023 (7)	0.0007 (6)
C9	0.0215 (9)	0.0160 (7)	0.0146 (8)	−0.0031 (6)	0.0038 (7)	−0.0019 (6)
C10	0.0228 (9)	0.0175 (8)	0.0167 (8)	−0.0003 (6)	0.0027 (7)	0.0036 (6)
C11	0.0201 (9)	0.0159 (8)	0.0202 (8)	−0.0004 (6)	0.0033 (7)	0.0000 (6)
C12	0.0233 (9)	0.0167 (8)	0.0146 (8)	−0.0024 (6)	0.0046 (7)	−0.0016 (6)
C13	0.0221 (9)	0.0150 (7)	0.0153 (8)	−0.0024 (6)	0.0004 (7)	0.0032 (6)
C14	0.0224 (9)	0.0141 (7)	0.0176 (8)	−0.0008 (6)	0.0029 (7)	−0.0002 (6)
C15	0.0312 (11)	0.0219 (9)	0.0260 (10)	0.0063 (7)	0.0017 (8)	0.0053 (7)
C16	0.0355 (11)	0.0311 (10)	0.0216 (9)	−0.0034 (8)	0.0032 (8)	−0.0087 (8)
C17	0.0320 (10)	0.0207 (8)	0.0217 (9)	0.0059 (7)	−0.0006 (8)	0.0031 (7)

S1—C7	1.6659 (17)	C4—H4A	0.9500
F1—C6	1.360 (2)	C5—C6	1.369 (2)
O1—C8	1.2337 (19)	C5—H5A	0.9500
O2—C11	1.359 (2)	C8—C9	1.485 (2)
O2—C15	1.435 (2)	C9—C10	1.395 (2)
O3—C12	1.3763 (19)	C9—C14	1.397 (2)
O3—C16	1.432 (2)	C10—C11	1.384 (2)
O4—C13	1.3660 (19)	C10—H10A	0.9500
O4—C17	1.425 (2)	C11—C12	1.403 (2)
N1—C7	1.339 (2)	C12—C13	1.396 (2)
N1—C1	1.410 (2)	C13—C14	1.388 (2)
N1—H1A	0.8800	C14—H14A	0.9500
N2—C8	1.381 (2)	C15—H15A	0.9800
N2—C7	1.404 (2)	C15—H15B	0.9800
N2—H2A	0.8800	C15—H15C	0.9800
C1—C2	1.387 (2)	C16—H16A	0.9800
C1—C6	1.392 (2)	C16—H16B	0.9800
C2—C3	1.391 (3)	C16—H16C	0.9800
C2—H2B	0.9500	C17—H17B	0.9800
C3—C4	1.389 (3)	C17—H17C	0.9800
C3—H3A	0.9500	C17—H17D	0.9800
C4—C5	1.379 (3)
C11—O2—C15	117.24 (13)	C14—C9—C8	122.59 (15)
C12—O3—C16	113.37 (13)	C11—C10—C9	119.76 (15)
C13—O4—C17	117.45 (13)	C11—C10—H10A	120.1
C7—N1—C1	130.78 (14)	C9—C10—H10A	120.1
C7—N1—H1A	114.6	O2—C11—C10	125.26 (15)
C1—N1—H1A	114.6	O2—C11—C12	115.17 (14)
C8—N2—C7	127.44 (14)	C10—C11—C12	119.56 (15)
C8—N2—H2A	116.3	O3—C12—C13	119.38 (14)
C7—N2—H2A	116.3	O3—C12—C11	120.47 (15)
C2—C1—C6	117.45 (16)	C13—C12—C11	120.13 (15)
C2—C1—N1	126.57 (15)	O4—C13—C14	124.86 (15)
C6—C1—N1	115.96 (15)	O4—C13—C12	114.50 (14)
C1—C2—C3	119.80 (17)	C14—C13—C12	120.63 (15)
C1—C2—H2B	120.1	C13—C14—C9	118.61 (15)
C3—C2—H2B	120.1	C13—C14—H14A	120.7
C4—C3—C2	121.17 (18)	C9—C14—H14A	120.7
C4—C3—H3A	119.4	O2—C15—H15A	109.5
C2—C3—H3A	119.4	O2—C15—H15B	109.5
C5—C4—C3	119.40 (17)	H15A—C15—H15B	109.5
C5—C4—H4A	120.3	O2—C15—H15C	109.5
C3—C4—H4A	120.3	H15A—C15—H15C	109.5
C6—C5—C4	118.79 (16)	H15B—C15—H15C	109.5
C6—C5—H5A	120.6	O3—C16—H16A	109.5
C4—C5—H5A	120.6	O3—C16—H16B	109.5
F1—C6—C5	119.23 (15)	H16A—C16—H16B	109.5
F1—C6—C1	117.40 (15)	O3—C16—H16C	109.5
C5—C6—C1	123.38 (17)	H16A—C16—H16C	109.5
N1—C7—N2	114.10 (14)	H16B—C16—H16C	109.5
N1—C7—S1	127.56 (13)	O4—C17—H17B	109.5
N2—C7—S1	118.34 (12)	O4—C17—H17C	109.5
O1—C8—N2	122.03 (15)	H17B—C17—H17C	109.5
O1—C8—C9	119.80 (15)	O4—C17—H17D	109.5
N2—C8—C9	118.16 (14)	H17B—C17—H17D	109.5
C10—C9—C14	121.30 (15)	H17C—C17—H17D	109.5
C10—C9—C8	115.80 (14)
C7—N1—C1—C2	−24.6 (3)	C14—C9—C10—C11	0.0 (3)
C7—N1—C1—C6	157.28 (18)	C8—C9—C10—C11	−173.74 (15)
C6—C1—C2—C3	−1.2 (3)	C15—O2—C11—C10	−5.8 (3)
N1—C1—C2—C3	−179.34 (19)	C15—O2—C11—C12	173.60 (15)
C1—C2—C3—C4	0.2 (3)	C9—C10—C11—O2	−179.91 (16)
C2—C3—C4—C5	0.8 (3)	C9—C10—C11—C12	0.7 (3)
C3—C4—C5—C6	−0.7 (3)	C16—O3—C12—C13	102.98 (18)
C4—C5—C6—F1	−179.93 (17)	C16—O3—C12—C11	−78.6 (2)
C4—C5—C6—C1	−0.3 (3)	O2—C11—C12—O3	1.5 (2)
C2—C1—C6—F1	−179.10 (16)	C10—C11—C12—O3	−179.01 (15)
N1—C1—C6—F1	−0.8 (3)	O2—C11—C12—C13	179.89 (15)
C2—C1—C6—C5	1.3 (3)	C10—C11—C12—C13	−0.6 (3)
N1—C1—C6—C5	179.62 (18)	C17—O4—C13—C14	−5.9 (2)
C1—N1—C7—N2	−177.33 (17)	C17—O4—C13—C12	175.70 (15)
C1—N1—C7—S1	2.7 (3)	O3—C12—C13—O4	−3.2 (2)
C8—N2—C7—N1	2.9 (3)	C11—C12—C13—O4	178.39 (15)
C8—N2—C7—S1	−177.17 (14)	O3—C12—C13—C14	178.27 (15)
C7—N2—C8—O1	4.8 (3)	C11—C12—C13—C14	−0.1 (3)
C7—N2—C8—C9	−174.22 (16)	O4—C13—C14—C9	−177.53 (16)
O1—C8—C9—C10	20.7 (3)	C12—C13—C14—C9	0.8 (3)
N2—C8—C9—C10	−160.21 (16)	C10—C9—C14—C13	−0.8 (3)
O1—C8—C9—C14	−152.96 (18)	C8—C9—C14—C13	172.57 (16)
N2—C8—C9—C14	26.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1i	0.88	2.70	3.5219 (15)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯S1i	0.88	2.70	3.5219 (15)	157

Symmetry code: (i) .