1,1-Dibenzyl-3-(4-fluoro-benzo-yl)thio-urea.

In the title compound, C(22)H(19)FN(2)OS, the 2-fluoro-benzoyl group adopts a trans conformation with respect to the thiono S atom across the N-C bond. In the crystal, inter-molecular N-H⋯S, C-H⋯S and C-H⋯O hydrogen bonds link the mol-ecules, forming a two-dimensional network parallel to (101).

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For related structures, see: Nasir et al. (2011 ▶); Yamin & Hassan (2004 ▶); Hassan et al. (2008a ▶,b ▶,c ▶, 2009 ▶). For the synthesis, see: Hassan et al. (2008a ▶).

Experimental

Crystal data

C22H19FN2OS

M = 378.45

Monoclinic,

a = 10.683 (3) Å

b = 7.026 (2) Å

c = 26.435 (7) Å

β = 101.100 (6)°

V = 1946.9 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 298 K

0.42 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.925, T max = 0.967

8644 measured reflections

3425 independent reflections

2659 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.138

S = 1.15

3425 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.23 e Å−3

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: ORTEPIII (Burnett & Johnson, 1996 ▶), XP in SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026687/dn2702sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026687/dn2702Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026687/dn2702Isup3.cml

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

C22H19FN2OS	F(000) = 792
Mr = 378.45	Dx = 1.291 Mg m−3
Monoclinic, P21/n	Melting point: 410 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.683 (3) Å	Cell parameters from 2659 reflections
b = 7.026 (2) Å	θ = 2.0–25.0°
c = 26.435 (7) Å	µ = 0.19 mm−1
β = 101.100 (6)°	T = 298 K
V = 1946.9 (10) Å3	Block, colourless
Z = 4	0.42 × 0.21 × 0.18 mm

Bruker SMART APEX CCD area-detector diffractometer	3425 independent reflections
Radiation source: fine-focus sealed tube	2659 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −12→8
Tmin = 0.925, Tmax = 0.967	k = −8→8
8644 measured reflections	l = −31→28

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0542P)2 + 0.5146P] where P = (Fo2 + 2Fc2)/3
3425 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.23 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 > 2sigma(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	0.8992 (2)	−0.7024 (3)	0.17795 (9)	0.1137 (8)
S1	0.47635 (8)	0.26603 (10)	0.02677 (3)	0.0641 (3)
O1	0.5719 (2)	0.0400 (3)	0.17142 (7)	0.0736 (6)
N1	0.5164 (2)	−0.0377 (3)	0.08698 (7)	0.0502 (6)
H1	0.5210	−0.1222	0.0639	0.060*
N2	0.3452 (2)	0.1514 (3)	0.09743 (7)	0.0453 (5)
C1	0.6626 (3)	−0.3835 (4)	0.11002 (10)	0.0570 (7)
H1A	0.6047	−0.3773	0.0789	0.068*
C2	0.7407 (3)	−0.5402 (5)	0.12067 (12)	0.0697 (8)
H2	0.7369	−0.6391	0.0970	0.084*
C3	0.8236 (3)	−0.5463 (5)	0.16670 (13)	0.0742 (9)
C4	0.8339 (3)	−0.4041 (6)	0.20216 (12)	0.0807 (10)
H4	0.8924	−0.4120	0.2331	0.097*
C5	0.7554 (3)	−0.2481 (5)	0.19116 (10)	0.0694 (9)
H5	0.7605	−0.1501	0.2151	0.083*
C6	0.6688 (2)	−0.2352 (4)	0.14481 (9)	0.0495 (6)
C7	0.5840 (2)	−0.0665 (4)	0.13658 (9)	0.0507 (7)
C8	0.4407 (3)	0.1238 (3)	0.07298 (8)	0.0460 (6)
C9	0.2742 (3)	0.3312 (4)	0.09357 (10)	0.0532 (7)
H9A	0.1842	0.3052	0.0815	0.064*
H9B	0.3027	0.4123	0.0683	0.064*
C10	0.2914 (3)	0.4349 (3)	0.14432 (9)	0.0482 (6)
C11	0.4099 (3)	0.4550 (4)	0.17540 (11)	0.0627 (8)
H11	0.4801	0.3968	0.1659	0.075*
C12	0.4261 (4)	0.5594 (5)	0.22019 (12)	0.0768 (10)
H12	0.5069	0.5718	0.2406	0.092*
C13	0.3240 (4)	0.6450 (4)	0.23477 (12)	0.0796 (10)
H13	0.3351	0.7164	0.2649	0.096*
C14	0.2052 (4)	0.6251 (4)	0.20481 (13)	0.0776 (10)
H14	0.1352	0.6823	0.2148	0.093*
C15	0.1887 (3)	0.5196 (4)	0.15949 (11)	0.0625 (8)
H15	0.1076	0.5062	0.1393	0.075*
C16	0.2919 (3)	0.0015 (4)	0.12613 (9)	0.0506 (7)
H16A	0.2790	0.0517	0.1589	0.061*
H16B	0.3517	−0.1036	0.1330	0.061*
C17	0.1667 (3)	−0.0689 (4)	0.09543 (9)	0.0521 (7)
C18	0.0539 (3)	−0.0329 (5)	0.11120 (12)	0.0716 (9)
H18	0.0539	0.0402	0.1405	0.086*
C19	−0.0598 (3)	−0.1044 (7)	0.08383 (17)	0.0976 (12)
H19	−0.1357	−0.0802	0.0950	0.117*
C20	−0.0607 (5)	−0.2105 (7)	0.04053 (17)	0.1034 (14)
H20	−0.1371	−0.2595	0.0224	0.124*
C21	0.0496 (5)	−0.2446 (5)	0.02384 (13)	0.0921 (12)
H21	0.0482	−0.3150	−0.0060	0.111*
C22	0.1643 (3)	−0.1750 (4)	0.05112 (11)	0.0680 (8)
H22	0.2398	−0.1996	0.0397	0.082*

	U11	U22	U33	U12	U13	U23
F1	0.1048 (16)	0.1189 (18)	0.1105 (16)	0.0546 (14)	0.0040 (13)	0.0346 (14)
S1	0.1037 (6)	0.0484 (4)	0.0428 (4)	−0.0095 (4)	0.0210 (4)	0.0047 (3)
O1	0.0912 (15)	0.0817 (15)	0.0405 (10)	0.0164 (12)	−0.0058 (10)	−0.0154 (10)
N1	0.0710 (14)	0.0460 (12)	0.0316 (10)	0.0060 (11)	0.0050 (10)	−0.0024 (9)
N2	0.0605 (13)	0.0358 (11)	0.0379 (11)	0.0003 (10)	0.0055 (10)	0.0029 (8)
C1	0.0627 (18)	0.0552 (17)	0.0482 (15)	0.0041 (15)	−0.0013 (13)	0.0088 (13)
C2	0.075 (2)	0.063 (2)	0.0670 (19)	0.0095 (17)	0.0033 (16)	0.0058 (15)
C3	0.064 (2)	0.087 (2)	0.072 (2)	0.0230 (18)	0.0127 (17)	0.0279 (19)
C4	0.064 (2)	0.121 (3)	0.0510 (18)	0.020 (2)	−0.0025 (15)	0.020 (2)
C5	0.0630 (18)	0.099 (3)	0.0424 (15)	0.0080 (19)	0.0008 (14)	0.0019 (15)
C6	0.0500 (15)	0.0624 (17)	0.0360 (13)	−0.0023 (14)	0.0080 (11)	0.0092 (12)
C7	0.0567 (16)	0.0580 (17)	0.0350 (13)	−0.0042 (14)	0.0027 (12)	−0.0001 (12)
C8	0.0644 (17)	0.0389 (14)	0.0309 (12)	−0.0067 (13)	−0.0007 (12)	−0.0060 (10)
C9	0.0685 (18)	0.0413 (15)	0.0468 (14)	0.0062 (14)	0.0038 (13)	0.0037 (11)
C10	0.0657 (17)	0.0346 (13)	0.0452 (14)	−0.0024 (13)	0.0125 (13)	0.0041 (11)
C11	0.072 (2)	0.0539 (18)	0.0614 (17)	−0.0025 (15)	0.0122 (15)	−0.0097 (14)
C12	0.101 (3)	0.065 (2)	0.0594 (19)	−0.012 (2)	0.0029 (18)	−0.0140 (16)
C13	0.143 (3)	0.0475 (19)	0.0521 (18)	−0.005 (2)	0.029 (2)	−0.0051 (14)
C14	0.118 (3)	0.0539 (19)	0.074 (2)	0.018 (2)	0.051 (2)	0.0056 (16)
C15	0.076 (2)	0.0505 (17)	0.0659 (18)	0.0077 (16)	0.0252 (16)	0.0086 (14)
C16	0.0652 (17)	0.0459 (15)	0.0415 (13)	0.0018 (13)	0.0126 (12)	0.0053 (11)
C17	0.0682 (18)	0.0428 (15)	0.0455 (14)	−0.0060 (14)	0.0114 (13)	0.0071 (12)
C18	0.074 (2)	0.078 (2)	0.0655 (19)	−0.0069 (18)	0.0196 (17)	0.0071 (16)
C19	0.067 (2)	0.127 (4)	0.098 (3)	−0.021 (2)	0.014 (2)	0.022 (3)
C20	0.100 (3)	0.116 (3)	0.083 (3)	−0.051 (3)	−0.011 (2)	0.022 (2)
C21	0.135 (4)	0.074 (2)	0.060 (2)	−0.038 (3)	0.001 (2)	−0.0021 (17)
C22	0.092 (2)	0.0541 (17)	0.0564 (17)	−0.0092 (17)	0.0109 (16)	−0.0003 (14)

F1—C3	1.360 (4)	C10—C11	1.376 (4)
S1—C8	1.678 (3)	C11—C12	1.375 (4)
O1—C7	1.213 (3)	C11—H11	0.9300
N1—C7	1.385 (3)	C12—C13	1.365 (5)
N1—C8	1.401 (3)	C12—H12	0.9300
N1—H1	0.8600	C13—C14	1.367 (5)
N2—C8	1.323 (3)	C13—H13	0.9300
N2—C9	1.467 (3)	C14—C15	1.391 (4)
N2—C16	1.475 (3)	C14—H14	0.9300
C1—C2	1.378 (4)	C15—H15	0.9300
C1—C6	1.383 (4)	C16—C17	1.508 (4)
C1—H1A	0.9300	C16—H16A	0.9700
C2—C3	1.361 (4)	C16—H16B	0.9700
C2—H2	0.9300	C17—C18	1.372 (4)
C3—C4	1.360 (5)	C17—C22	1.385 (4)
C4—C5	1.376 (4)	C18—C19	1.383 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.389 (4)	C19—C20	1.364 (6)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.482 (4)	C20—C21	1.356 (6)
C9—C10	1.507 (3)	C20—H20	0.9300
C9—H9A	0.9700	C21—C22	1.386 (5)
C9—H9B	0.9700	C21—H21	0.9300
C10—C15	1.375 (4)	C22—H22	0.9300
C7—N1—C8	122.6 (2)	C12—C11—C10	121.2 (3)
C7—N1—H1	118.7	C12—C11—H11	119.4
C8—N1—H1	118.7	C10—C11—H11	119.4
C8—N2—C9	122.0 (2)	C13—C12—C11	120.2 (3)
C8—N2—C16	123.8 (2)	C13—C12—H12	119.9
C9—N2—C16	113.9 (2)	C11—C12—H12	119.9
C2—C1—C6	121.1 (3)	C12—C13—C14	119.6 (3)
C2—C1—H1A	119.4	C12—C13—H13	120.2
C6—C1—H1A	119.4	C14—C13—H13	120.2
C3—C2—C1	118.2 (3)	C13—C14—C15	120.2 (3)
C3—C2—H2	120.9	C13—C14—H14	119.9
C1—C2—H2	120.9	C15—C14—H14	119.9
C4—C3—F1	118.4 (3)	C10—C15—C14	120.4 (3)
C4—C3—C2	123.0 (3)	C10—C15—H15	119.8
F1—C3—C2	118.5 (3)	C14—C15—H15	119.8
C3—C4—C5	118.3 (3)	N2—C16—C17	110.32 (19)
C3—C4—H4	120.8	N2—C16—H16A	109.6
C5—C4—H4	120.8	C17—C16—H16A	109.6
C4—C5—C6	120.9 (3)	N2—C16—H16B	109.6
C4—C5—H5	119.5	C17—C16—H16B	109.6
C6—C5—H5	119.5	H16A—C16—H16B	108.1
C1—C6—C5	118.4 (3)	C18—C17—C22	118.8 (3)
C1—C6—C7	123.7 (2)	C18—C17—C16	121.1 (3)
C5—C6—C7	117.8 (3)	C22—C17—C16	120.1 (3)
O1—C7—N1	121.1 (2)	C17—C18—C19	120.5 (3)
O1—C7—C6	122.2 (2)	C17—C18—H18	119.7
N1—C7—C6	116.7 (2)	C19—C18—H18	119.7
N2—C8—N1	116.7 (2)	C20—C19—C18	120.1 (4)
N2—C8—S1	124.9 (2)	C20—C19—H19	120.0
N1—C8—S1	118.3 (2)	C18—C19—H19	120.0
N2—C9—C10	112.4 (2)	C21—C20—C19	120.2 (4)
N2—C9—H9A	109.1	C21—C20—H20	119.9
C10—C9—H9A	109.1	C19—C20—H20	119.9
N2—C9—H9B	109.1	C20—C21—C22	120.3 (4)
C10—C9—H9B	109.1	C20—C21—H21	119.8
H9A—C9—H9B	107.8	C22—C21—H21	119.8
C15—C10—C11	118.4 (3)	C17—C22—C21	120.0 (3)
C15—C10—C9	120.1 (3)	C17—C22—H22	120.0
C11—C10—C9	121.5 (3)	C21—C22—H22	120.0

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···S1	0.97	2.55	3.076 (3)	114
N1—H1···S1i	0.86	2.61	3.422 (2)	159
C1—H1A···S1i	0.93	2.87	3.727 (3)	154
C4—H4···O1ii	0.93	2.50	3.322 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.86	2.61	3.422 (2)	159
C1—H1A⋯S1i	0.93	2.87	3.727 (3)	154
C4—H4⋯O1ii	0.93	2.50	3.322 (4)	147

Symmetry codes: (i) ; (ii) .