1-(Adamantan-1-ylcarbon-yl)-3-(2,6-difluoro-4-hy-droxy-phen-yl)thio-urea.

In the title mol-ecule, C(18)H(20)F(2)N(2)O(2)S, the 2,6-difluoro-4-hy-droxy-phenyl ring and the carbonyl-thio-urea group are each essentially planar, with maximum deviations of atoms from their mean planes of 0.0113 (14) and 0.1017 (15) Å, respectively; the dihedral angle between these two planes is 71.03 (6)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, N-H⋯O and O-H⋯S hydrogen bonds connect the mol-ecules into chains running diagonally across the bc plane. C-H⋯S and C-H⋯F contacts are also observed.

Related literature

For background studies of thio­urea derivatives, see: Saeed et al. (2011 ▶). For a related structure, see: Saeed et al. (2010 ▶).

Experimental

Crystal data

C18H20F2N2O2S

M = 366.42

Triclinic,

a = 7.3985 (9) Å

b = 10.4953 (13) Å

c = 12.4094 (15) Å

α = 65.554 (2)°

β = 79.372 (2)°

γ = 89.766 (2)°

V = 859.34 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.38 × 0.36 × 0.08 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.920, T max = 0.982

4824 measured reflections

2976 independent reflections

2399 reflections with I > 2σ(I)

R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.100

S = 1.04

2976 reflections

238 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018806/pv2537sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018806/pv2537Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018806/pv2537Isup3.cml

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

C18H20F2N2O2S	Z = 2
Mr = 366.42	F(000) = 384
Triclinic, P1	Dx = 1.416 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3985 (9) Å	Cell parameters from 4824 reflections
b = 10.4953 (13) Å	θ = 2.8–25.0°
c = 12.4094 (15) Å	µ = 0.22 mm−1
α = 65.554 (2)°	T = 296 K
β = 79.372 (2)°	Plate, colourless
γ = 89.766 (2)°	0.38 × 0.36 × 0.08 mm
V = 859.34 (18) Å3

Bruker SMART 1000 CCD diffractometer	2976 independent reflections
Radiation source: fine-focus sealed tube	2399 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.010
ω & φ scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −8→8
Tmin = 0.920, Tmax = 0.982	k = −9→12
4824 measured reflections	l = −14→14

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0409P)2 + 0.3498P] where P = (Fo2 + 2Fc2)/3
2976 reflections	(Δ/σ)max < 0.001
238 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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
S1	0.98449 (8)	−0.02031 (6)	0.68281 (5)	0.05290 (18)
F1	1.3675 (2)	0.16253 (18)	0.66290 (12)	0.0801 (5)
F2	0.81301 (19)	0.25665 (16)	0.85556 (13)	0.0769 (4)
O1	1.2972 (3)	0.08462 (19)	1.06720 (15)	0.0659 (5)
H1O	1.212 (4)	0.076 (3)	1.128 (3)	0.095 (11)*
O2	0.8566 (3)	0.42734 (17)	0.47025 (18)	0.0918 (7)
N1	1.0107 (3)	0.2470 (2)	0.64901 (16)	0.0533 (5)
H1	0.993 (3)	0.327 (3)	0.613 (2)	0.061 (7)*
N2	0.8692 (3)	0.19619 (19)	0.51851 (15)	0.0481 (4)
H2	0.838 (3)	0.132 (2)	0.5017 (18)	0.046 (6)*
C1	1.0863 (3)	0.2106 (2)	0.75458 (17)	0.0465 (5)
C2	1.2611 (3)	0.1657 (2)	0.76211 (18)	0.0508 (5)
C3	1.3321 (3)	0.1234 (2)	0.86477 (18)	0.0521 (5)
H3	1.4501	0.0926	0.8662	0.063*
C4	1.2233 (3)	0.1278 (2)	0.96622 (17)	0.0467 (5)
C5	1.0489 (3)	0.1751 (2)	0.96344 (18)	0.0491 (5)
H5	0.9768	0.1803	1.0311	0.059*
C6	0.9851 (3)	0.2141 (2)	0.85798 (19)	0.0484 (5)
C7	0.9559 (3)	0.1514 (2)	0.61553 (16)	0.0433 (5)
C8	0.8121 (3)	0.3264 (2)	0.45461 (19)	0.0517 (5)
C9	0.6926 (3)	0.3338 (2)	0.36480 (16)	0.0417 (4)
C10	0.5468 (3)	0.4380 (2)	0.3671 (2)	0.0615 (6)
H10A	0.4691	0.4041	0.4471	0.074*
H10B	0.6072	0.5285	0.3488	0.074*
C11	0.4287 (4)	0.4539 (3)	0.2740 (3)	0.0733 (8)
H11	0.3357	0.5200	0.2761	0.088*
C12	0.3332 (3)	0.3132 (3)	0.3014 (3)	0.0759 (8)
H12A	0.2537	0.2768	0.3810	0.091*
H12B	0.2573	0.3246	0.2426	0.091*
C13	0.4766 (3)	0.2112 (2)	0.2971 (2)	0.0541 (5)
H13	0.4143	0.1204	0.3151	0.065*
C14	0.5933 (3)	0.1922 (2)	0.39204 (18)	0.0457 (5)
H14A	0.6834	0.1251	0.3912	0.055*
H14B	0.5145	0.1559	0.4718	0.055*
C15	0.8154 (3)	0.3888 (3)	0.23861 (19)	0.0575 (6)
H15A	0.9072	0.3232	0.2363	0.069*
H15B	0.8793	0.4783	0.2197	0.069*
C16	0.6960 (4)	0.4067 (3)	0.1452 (2)	0.0684 (7)
H16	0.7744	0.4432	0.0643	0.082*
C17	0.6014 (3)	0.2650 (3)	0.1738 (2)	0.0631 (6)
H17A	0.5297	0.2744	0.1133	0.076*
H17B	0.6932	0.1990	0.1728	0.076*
C18	0.5517 (4)	0.5102 (3)	0.1499 (2)	0.0811 (9)
H18A	0.6129	0.6003	0.1320	0.097*
H18B	0.4778	0.5238	0.0896	0.097*

	U11	U22	U33	U12	U13	U23
S1	0.0726 (4)	0.0439 (3)	0.0474 (3)	0.0169 (3)	−0.0265 (3)	−0.0185 (2)
F1	0.0762 (10)	0.1176 (13)	0.0479 (8)	0.0208 (9)	−0.0104 (7)	−0.0372 (8)
F2	0.0675 (9)	0.0973 (11)	0.0828 (10)	0.0420 (8)	−0.0378 (8)	−0.0454 (9)
O1	0.0662 (11)	0.0889 (13)	0.0456 (9)	0.0123 (9)	−0.0283 (8)	−0.0240 (9)
O2	0.1500 (18)	0.0459 (10)	0.1119 (15)	0.0241 (10)	−0.0993 (14)	−0.0348 (10)
N1	0.0806 (14)	0.0408 (10)	0.0478 (10)	0.0158 (10)	−0.0380 (10)	−0.0175 (9)
N2	0.0674 (12)	0.0421 (10)	0.0468 (10)	0.0137 (9)	−0.0317 (9)	−0.0221 (8)
C1	0.0626 (13)	0.0406 (11)	0.0417 (11)	0.0084 (10)	−0.0255 (10)	−0.0165 (9)
C2	0.0556 (13)	0.0596 (13)	0.0379 (11)	0.0067 (10)	−0.0114 (9)	−0.0203 (10)
C3	0.0463 (12)	0.0630 (14)	0.0465 (12)	0.0087 (10)	−0.0163 (9)	−0.0194 (10)
C4	0.0523 (12)	0.0483 (12)	0.0398 (11)	0.0010 (9)	−0.0199 (9)	−0.0142 (9)
C5	0.0561 (13)	0.0529 (12)	0.0414 (11)	0.0070 (10)	−0.0134 (9)	−0.0214 (10)
C6	0.0515 (12)	0.0458 (11)	0.0549 (12)	0.0139 (9)	−0.0240 (10)	−0.0226 (10)
C7	0.0497 (11)	0.0473 (11)	0.0370 (10)	0.0114 (9)	−0.0172 (9)	−0.0183 (9)
C8	0.0689 (14)	0.0439 (12)	0.0497 (12)	0.0104 (10)	−0.0311 (11)	−0.0192 (10)
C9	0.0494 (11)	0.0394 (10)	0.0394 (10)	0.0077 (9)	−0.0197 (9)	−0.0152 (9)
C10	0.0797 (16)	0.0561 (14)	0.0650 (14)	0.0285 (12)	−0.0339 (12)	−0.0335 (12)
C11	0.0812 (18)	0.0689 (17)	0.0902 (19)	0.0416 (14)	−0.0524 (16)	−0.0393 (15)
C12	0.0513 (14)	0.090 (2)	0.096 (2)	0.0159 (13)	−0.0330 (14)	−0.0404 (16)
C13	0.0497 (12)	0.0524 (13)	0.0647 (14)	0.0012 (10)	−0.0258 (11)	−0.0232 (11)
C14	0.0472 (11)	0.0448 (11)	0.0428 (11)	0.0029 (9)	−0.0128 (9)	−0.0145 (9)
C15	0.0553 (13)	0.0594 (14)	0.0500 (12)	−0.0110 (11)	−0.0106 (10)	−0.0152 (11)
C16	0.0849 (18)	0.0748 (17)	0.0357 (11)	−0.0125 (14)	−0.0149 (11)	−0.0124 (11)
C17	0.0784 (16)	0.0709 (16)	0.0530 (13)	0.0091 (13)	−0.0310 (12)	−0.0314 (12)
C18	0.124 (2)	0.0520 (14)	0.0721 (17)	0.0101 (15)	−0.0662 (17)	−0.0112 (13)

S1—C7	1.675 (2)	C10—C11	1.529 (3)
F1—C2	1.346 (2)	C10—H10A	0.9700
F2—C6	1.349 (2)	C10—H10B	0.9700
O1—C4	1.362 (2)	C11—C18	1.512 (4)
O1—H1O	0.87 (3)	C11—C12	1.517 (4)
O2—C8	1.211 (2)	C11—H11	0.9800
N1—C7	1.325 (3)	C12—C13	1.514 (3)
N1—C1	1.425 (2)	C12—H12A	0.9700
N1—H1	0.79 (2)	C12—H12B	0.9700
N2—C7	1.377 (2)	C13—C17	1.510 (3)
N2—C8	1.377 (3)	C13—C14	1.534 (3)
N2—H2	0.83 (2)	C13—H13	0.9800
C1—C6	1.376 (3)	C14—H14A	0.9700
C1—C2	1.380 (3)	C14—H14B	0.9700
C2—C3	1.369 (3)	C15—C16	1.535 (3)
C3—C4	1.382 (3)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—C5	1.382 (3)	C16—C17	1.519 (3)
C5—C6	1.373 (3)	C16—C18	1.531 (4)
C5—H5	0.9300	C16—H16	0.9800
C8—C9	1.523 (2)	C17—H17A	0.9700
C9—C15	1.531 (3)	C17—H17B	0.9700
C9—C10	1.538 (3)	C18—H18A	0.9700
C9—C14	1.538 (3)	C18—H18B	0.9700
C4—O1—H1O	109 (2)	C18—C11—H11	109.4
C7—N1—C1	122.30 (17)	C12—C11—H11	109.4
C7—N1—H1	119.5 (17)	C10—C11—H11	109.4
C1—N1—H1	118.0 (17)	C13—C12—C11	109.5 (2)
C7—N2—C8	129.89 (18)	C13—C12—H12A	109.8
C7—N2—H2	113.5 (14)	C11—C12—H12A	109.8
C8—N2—H2	116.3 (14)	C13—C12—H12B	109.8
C6—C1—C2	115.57 (17)	C11—C12—H12B	109.8
C6—C1—N1	121.27 (19)	H12A—C12—H12B	108.2
C2—C1—N1	123.14 (19)	C17—C13—C12	110.9 (2)
F1—C2—C3	118.07 (19)	C17—C13—C14	109.09 (17)
F1—C2—C1	118.10 (17)	C12—C13—C14	109.23 (19)
C3—C2—C1	123.83 (19)	C17—C13—H13	109.2
C2—C3—C4	118.00 (19)	C12—C13—H13	109.2
C2—C3—H3	121.0	C14—C13—H13	109.2
C4—C3—H3	121.0	C13—C14—C9	109.91 (16)
O1—C4—C5	122.39 (19)	C13—C14—H14A	109.7
O1—C4—C3	116.74 (19)	C9—C14—H14A	109.7
C5—C4—C3	120.87 (17)	C13—C14—H14B	109.7
C6—C5—C4	118.13 (19)	C9—C14—H14B	109.7
C6—C5—H5	120.9	H14A—C14—H14B	108.2
C4—C5—H5	120.9	C9—C15—C16	109.42 (18)
F2—C6—C5	118.48 (19)	C9—C15—H15A	109.8
F2—C6—C1	117.93 (17)	C16—C15—H15A	109.8
C5—C6—C1	123.58 (19)	C9—C15—H15B	109.8
N1—C7—N2	117.75 (17)	C16—C15—H15B	109.8
N1—C7—S1	124.67 (14)	H15A—C15—H15B	108.2
N2—C7—S1	117.59 (15)	C17—C16—C18	110.1 (2)
O2—C8—N2	120.81 (18)	C17—C16—C15	109.17 (19)
O2—C8—C9	123.18 (18)	C18—C16—C15	109.3 (2)
N2—C8—C9	116.01 (17)	C17—C16—H16	109.4
C8—C9—C15	108.41 (17)	C18—C16—H16	109.4
C8—C9—C10	107.81 (16)	C15—C16—H16	109.4
C15—C9—C10	109.33 (17)	C13—C17—C16	109.20 (19)
C8—C9—C14	114.03 (15)	C13—C17—H17A	109.8
C15—C9—C14	108.57 (16)	C16—C17—H17A	109.8
C10—C9—C14	108.62 (17)	C13—C17—H17B	109.8
C11—C10—C9	109.65 (17)	C16—C17—H17B	109.8
C11—C10—H10A	109.7	H17A—C17—H17B	108.3
C9—C10—H10A	109.7	C11—C18—C16	109.77 (19)
C11—C10—H10B	109.7	C11—C18—H18A	109.7
C9—C10—H10B	109.7	C16—C18—H18A	109.7
H10A—C10—H10B	108.2	C11—C18—H18B	109.7
C18—C11—C12	109.5 (2)	C16—C18—H18B	109.7
C18—C11—C10	108.9 (2)	H18A—C18—H18B	108.2
C12—C11—C10	110.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.79 (2)	2.09 (2)	2.692 (2)	133 (2)
N1—H1···O2i	0.79 (2)	2.52 (2)	3.185 (3)	142 (2)
O1—H1O···S1ii	0.87 (3)	2.36 (3)	3.212 (2)	169 (3)
C14—H14A···S1iii	0.97	2.84	3.761 (2)	159
C14—H14B···F1iv	0.97	2.45	3.354 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.79 (2)	2.09 (2)	2.692 (2)	133 (2)
N1—H1⋯O2i	0.79 (2)	2.52 (2)	3.185 (3)	142 (2)
O1—H1O⋯S1ii	0.87 (3)	2.36 (3)	3.212 (2)	169 (3)
C14—H14A⋯S1iii	0.97	2.84	3.761 (2)	159
C14—H14B⋯F1iv	0.97	2.45	3.354 (3)	155

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