5-(Adamantan-1-yl)-3-anilinomethyl-2,3-di-hydro-1,3,4-oxa-diazole-2-thione.

In the title compound, C19H23N3OS, the oxa-diazole and benzene rings are inclined at a dihedral angle of 50.30 (11)°, with the major twist between them occurring at the ring-methyl-ene N-C bond [N-N-C-N torsion angle = -101.2 (2)°]. In the crystal, helical supra-molecular chains along [010] are sustained by N-H⋯S hydrogen bonds. These are linked into layers lying parallel to (-101) by methyl-ene-phenyl C-H⋯π inter-actions.

Related literature

For the anti-viral and anti-inflammatory activity of adamantane derivatives, see: El-Emam et al. (2004 ▶); El-Emam & Ibrahim (1991 ▶). For the structure of the 4-fluoro derivative, see: Al-Tamimi et al. (2013 ▶).

Experimental

Crystal data

C19H23N3OS

M = 341.46

Monoclinic,

a = 14.1326 (13) Å

b = 7.1179 (5) Å

c = 18.3685 (16) Å

β = 105.546 (10)°

V = 1780.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 295 K

0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.863, T max = 1.000

12073 measured reflections

4115 independent reflections

2827 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.131

S = 1.03

4115 reflections

221 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813009835/hb7068sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009835/hb7068Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009835/hb7068Isup3.cml

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

C19H23N3OS	F(000) = 728
Mr = 341.46	Dx = 1.274 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2861 reflections
a = 14.1326 (13) Å	θ = 2.9–27.5°
b = 7.1179 (5) Å	µ = 0.19 mm−1
c = 18.3685 (16) Å	T = 295 K
β = 105.546 (10)°	Prism, colourless
V = 1780.2 (3) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	4115 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2827 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.033
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.0°
ω scan	h = −16→18
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −7→9
Tmin = 0.863, Tmax = 1.000	l = −23→22
12073 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0529P)2 + 0.3647P] where P = (Fo2 + 2Fc2)/3
4115 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.27 e Å−3
1 restraint	Δρmin = −0.21 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	0.24181 (4)	0.53985 (8)	0.68790 (3)	0.05916 (19)
O1	0.37654 (9)	0.79478 (17)	0.67903 (7)	0.0445 (3)
N1	0.40128 (11)	0.6798 (2)	0.79036 (8)	0.0443 (4)
N2	0.47627 (11)	0.8094 (2)	0.79447 (8)	0.0439 (4)
N3	0.42471 (14)	0.4044 (3)	0.87149 (10)	0.0572 (5)
H3	0.3797 (12)	0.317 (2)	0.8616 (12)	0.064 (7)*
C1	0.33997 (14)	0.6695 (2)	0.72114 (10)	0.0434 (4)
C2	0.45822 (13)	0.8739 (2)	0.72695 (9)	0.0387 (4)
C3	0.51147 (13)	1.0228 (2)	0.69660 (9)	0.0380 (4)
C4	0.44544 (15)	1.1970 (3)	0.67713 (12)	0.0521 (5)
H4A	0.3850	1.1644	0.6397	0.063*
H4B	0.4288	1.2415	0.7220	0.063*
C5	0.49874 (17)	1.3518 (3)	0.64617 (13)	0.0600 (6)
H5	0.4563	1.4627	0.6340	0.072*
C6	0.52324 (16)	1.2811 (3)	0.57462 (12)	0.0601 (6)
H6A	0.4632	1.2484	0.5368	0.072*
H6B	0.5562	1.3793	0.5541	0.072*
C7	0.58959 (15)	1.1093 (3)	0.59392 (10)	0.0499 (5)
H7	0.6054	1.0647	0.5481	0.060*
C8	0.53678 (15)	0.9534 (3)	0.62449 (10)	0.0445 (4)
H8A	0.5786	0.8433	0.6360	0.053*
H8B	0.4771	0.9188	0.5867	0.053*
C9	0.60678 (14)	1.0759 (3)	0.75559 (9)	0.0445 (4)
H9A	0.5919	1.1190	0.8014	0.053*
H9B	0.6490	0.9665	0.7680	0.053*
C10	0.65936 (15)	1.2308 (3)	0.72437 (11)	0.0516 (5)
H10	0.7201	1.2644	0.7624	0.062*
C11	0.59323 (18)	1.4034 (3)	0.70569 (13)	0.0638 (6)
H11A	0.6270	1.5030	0.6867	0.077*
H11B	0.5777	1.4484	0.7510	0.077*
C12	0.68424 (15)	1.1618 (3)	0.65259 (11)	0.0525 (5)
H12A	0.7180	1.2601	0.6329	0.063*
H12B	0.7272	1.0534	0.6642	0.063*
C13	0.38778 (16)	0.5893 (3)	0.85927 (11)	0.0539 (5)
H13A	0.4199	0.6655	0.9026	0.065*
H13B	0.3182	0.5869	0.8562	0.065*
C14	0.51825 (16)	0.3569 (3)	0.91240 (10)	0.0501 (5)
C15	0.59359 (18)	0.4873 (4)	0.93158 (12)	0.0721 (7)
H15	0.5821	0.6127	0.9178	0.087*
C16	0.6873 (2)	0.4277 (6)	0.97194 (15)	0.0973 (11)
H16	0.7381	0.5145	0.9856	0.117*
C17	0.7051 (2)	0.2421 (6)	0.99156 (16)	0.1006 (11)
H17	0.7679	0.2037	1.0178	0.121*
C18	0.6307 (2)	0.1144 (5)	0.97258 (14)	0.0864 (9)
H18	0.6427	−0.0112	0.9858	0.104*
C19	0.53828 (19)	0.1709 (3)	0.93402 (11)	0.0643 (6)
H19	0.4878	0.0830	0.9220	0.077*

	U11	U22	U33	U12	U13	U23
S1	0.0456 (3)	0.0447 (3)	0.0819 (4)	−0.0051 (2)	0.0079 (3)	0.0002 (2)
O1	0.0420 (7)	0.0413 (7)	0.0474 (7)	−0.0013 (6)	0.0072 (6)	0.0018 (5)
N1	0.0449 (9)	0.0411 (8)	0.0483 (8)	−0.0022 (8)	0.0147 (7)	0.0023 (6)
N2	0.0435 (9)	0.0417 (8)	0.0467 (8)	−0.0038 (8)	0.0126 (7)	0.0011 (7)
N3	0.0549 (11)	0.0478 (10)	0.0605 (10)	−0.0125 (9)	0.0007 (9)	0.0073 (8)
C1	0.0428 (10)	0.0340 (9)	0.0558 (11)	0.0045 (8)	0.0171 (9)	0.0021 (8)
C2	0.0375 (10)	0.0371 (9)	0.0412 (9)	0.0024 (8)	0.0101 (8)	−0.0024 (7)
C3	0.0389 (10)	0.0354 (9)	0.0403 (9)	0.0024 (8)	0.0115 (8)	−0.0006 (7)
C4	0.0488 (12)	0.0452 (11)	0.0661 (12)	0.0104 (10)	0.0217 (10)	0.0070 (9)
C5	0.0618 (14)	0.0390 (10)	0.0846 (15)	0.0146 (10)	0.0291 (12)	0.0150 (10)
C6	0.0578 (13)	0.0620 (13)	0.0601 (12)	0.0056 (11)	0.0154 (11)	0.0230 (10)
C7	0.0545 (12)	0.0577 (12)	0.0401 (9)	0.0046 (10)	0.0173 (9)	0.0026 (8)
C8	0.0491 (11)	0.0428 (10)	0.0412 (9)	0.0030 (9)	0.0117 (8)	−0.0023 (7)
C9	0.0454 (11)	0.0485 (11)	0.0400 (9)	−0.0011 (9)	0.0117 (8)	−0.0012 (8)
C10	0.0492 (11)	0.0535 (12)	0.0508 (11)	−0.0106 (10)	0.0115 (9)	−0.0037 (9)
C11	0.0811 (17)	0.0411 (11)	0.0773 (14)	−0.0083 (12)	0.0352 (13)	−0.0054 (10)
C12	0.0461 (11)	0.0593 (12)	0.0550 (11)	0.0023 (10)	0.0188 (9)	0.0079 (9)
C13	0.0588 (13)	0.0555 (12)	0.0532 (11)	−0.0052 (11)	0.0250 (10)	0.0048 (9)
C14	0.0522 (12)	0.0644 (13)	0.0340 (9)	−0.0061 (11)	0.0121 (9)	0.0013 (8)
C15	0.0603 (15)	0.0996 (19)	0.0548 (12)	−0.0252 (14)	0.0124 (11)	0.0134 (12)
C16	0.0567 (17)	0.168 (3)	0.0676 (16)	−0.032 (2)	0.0168 (14)	0.0173 (19)
C17	0.0655 (19)	0.173 (4)	0.0645 (16)	0.026 (2)	0.0193 (15)	0.025 (2)
C18	0.093 (2)	0.106 (2)	0.0594 (14)	0.032 (2)	0.0173 (15)	0.0027 (14)
C19	0.0756 (16)	0.0685 (15)	0.0453 (11)	0.0103 (13)	0.0101 (11)	−0.0020 (10)

S1—C1	1.642 (2)	C8—H8A	0.9700
O1—C1	1.369 (2)	C8—H8B	0.9700
O1—C2	1.371 (2)	C9—C10	1.525 (3)
N1—C1	1.335 (2)	C9—H9A	0.9700
N1—N2	1.392 (2)	C9—H9B	0.9700
N1—C13	1.478 (2)	C10—C11	1.526 (3)
N2—C2	1.283 (2)	C10—C12	1.533 (3)
N3—C14	1.376 (3)	C10—H10	0.9800
N3—C13	1.411 (3)	C11—H11A	0.9700
N3—H3	0.872 (10)	C11—H11B	0.9700
C2—C3	1.492 (2)	C12—H12A	0.9700
C3—C9	1.533 (3)	C12—H12B	0.9700
C3—C4	1.535 (2)	C13—H13A	0.9700
C3—C8	1.543 (2)	C13—H13B	0.9700
C4—C5	1.528 (3)	C14—C15	1.385 (3)
C4—H4A	0.9700	C14—C19	1.389 (3)
C4—H4B	0.9700	C15—C16	1.399 (4)
C5—C11	1.527 (3)	C15—H15	0.9300
C5—C6	1.531 (3)	C16—C17	1.375 (5)
C5—H5	0.9800	C16—H16	0.9300
C6—C7	1.524 (3)	C17—C18	1.363 (4)
C6—H6A	0.9700	C17—H17	0.9300
C6—H6B	0.9700	C18—C19	1.368 (3)
C7—C12	1.522 (3)	C18—H18	0.9300
C7—C8	1.526 (3)	C19—H19	0.9300
C7—H7	0.9800
C1—O1—C2	106.57 (13)	H8A—C8—H8B	108.2
C1—N1—N2	112.24 (14)	C10—C9—C3	109.68 (15)
C1—N1—C13	126.30 (16)	C10—C9—H9A	109.7
N2—N1—C13	120.92 (15)	C3—C9—H9A	109.7
C2—N2—N1	103.52 (15)	C10—C9—H9B	109.7
C14—N3—C13	125.16 (19)	C3—C9—H9B	109.7
C14—N3—H3	118.6 (15)	H9A—C9—H9B	108.2
C13—N3—H3	114.4 (15)	C9—C10—C11	109.63 (16)
N1—C1—O1	104.80 (15)	C9—C10—C12	109.81 (16)
N1—C1—S1	130.78 (14)	C11—C10—C12	109.40 (16)
O1—C1—S1	124.43 (14)	C9—C10—H10	109.3
N2—C2—O1	112.87 (15)	C11—C10—H10	109.3
N2—C2—C3	128.79 (16)	C12—C10—H10	109.3
O1—C2—C3	118.31 (14)	C10—C11—C5	109.43 (17)
C2—C3—C9	110.28 (14)	C10—C11—H11A	109.8
C2—C3—C4	108.94 (14)	C5—C11—H11A	109.8
C9—C3—C4	109.27 (15)	C10—C11—H11B	109.8
C2—C3—C8	110.47 (14)	C5—C11—H11B	109.8
C9—C3—C8	108.90 (14)	H11A—C11—H11B	108.2
C4—C3—C8	108.96 (14)	C7—C12—C10	109.08 (15)
C5—C4—C3	109.84 (15)	C7—C12—H12A	109.9
C5—C4—H4A	109.7	C10—C12—H12A	109.9
C3—C4—H4A	109.7	C7—C12—H12B	109.9
C5—C4—H4B	109.7	C10—C12—H12B	109.9
C3—C4—H4B	109.7	H12A—C12—H12B	108.3
H4A—C4—H4B	108.2	N3—C13—N1	114.57 (16)
C4—C5—C11	109.33 (17)	N3—C13—H13A	108.6
C4—C5—C6	109.28 (17)	N1—C13—H13A	108.6
C11—C5—C6	109.76 (18)	N3—C13—H13B	108.6
C4—C5—H5	109.5	N1—C13—H13B	108.6
C11—C5—H5	109.5	H13A—C13—H13B	107.6
C6—C5—H5	109.5	N3—C14—C15	122.3 (2)
C7—C6—C5	109.30 (16)	N3—C14—C19	118.8 (2)
C7—C6—H6A	109.8	C15—C14—C19	118.8 (2)
C5—C6—H6A	109.8	C14—C15—C16	119.0 (3)
C7—C6—H6B	109.8	C14—C15—H15	120.5
C5—C6—H6B	109.8	C16—C15—H15	120.5
H6A—C6—H6B	108.3	C17—C16—C15	120.7 (3)
C12—C7—C6	109.66 (17)	C17—C16—H16	119.6
C12—C7—C8	109.99 (15)	C15—C16—H16	119.6
C6—C7—C8	109.76 (15)	C18—C17—C16	120.0 (3)
C12—C7—H7	109.1	C18—C17—H17	120.0
C6—C7—H7	109.1	C16—C17—H17	120.0
C8—C7—H7	109.1	C17—C18—C19	120.0 (3)
C7—C8—C3	109.39 (14)	C17—C18—H18	120.0
C7—C8—H8A	109.8	C19—C18—H18	120.0
C3—C8—H8A	109.8	C18—C19—C14	121.4 (3)
C7—C8—H8B	109.8	C18—C19—H19	119.3
C3—C8—H8B	109.8	C14—C19—H19	119.3
C1—N1—N2—C2	−0.20 (19)	C2—C3—C8—C7	179.05 (15)
C13—N1—N2—C2	−172.34 (16)	C9—C3—C8—C7	−59.69 (19)
N2—N1—C1—O1	0.44 (19)	C4—C3—C8—C7	59.4 (2)
C13—N1—C1—O1	172.06 (15)	C2—C3—C9—C10	−178.88 (14)
N2—N1—C1—S1	179.88 (13)	C4—C3—C9—C10	−59.16 (18)
C13—N1—C1—S1	−8.5 (3)	C8—C3—C9—C10	59.75 (19)
C2—O1—C1—N1	−0.49 (17)	C3—C9—C10—C11	60.0 (2)
C2—O1—C1—S1	−179.97 (13)	C3—C9—C10—C12	−60.2 (2)
N1—N2—C2—O1	−0.13 (18)	C9—C10—C11—C5	−60.5 (2)
N1—N2—C2—C3	177.74 (16)	C12—C10—C11—C5	60.0 (2)
C1—O1—C2—N2	0.40 (19)	C4—C5—C11—C10	60.3 (2)
C1—O1—C2—C3	−177.71 (14)	C6—C5—C11—C10	−59.6 (2)
N2—C2—C3—C9	9.1 (2)	C6—C7—C12—C10	60.7 (2)
O1—C2—C3—C9	−173.15 (14)	C8—C7—C12—C10	−60.1 (2)
N2—C2—C3—C4	−110.8 (2)	C9—C10—C12—C7	59.9 (2)
O1—C2—C3—C4	66.93 (19)	C11—C10—C12—C7	−60.5 (2)
N2—C2—C3—C8	129.51 (19)	C14—N3—C13—N1	90.8 (2)
O1—C2—C3—C8	−52.7 (2)	C1—N1—C13—N3	87.8 (2)
C2—C3—C4—C5	179.79 (16)	N2—N1—C13—N3	−101.2 (2)
C9—C3—C4—C5	59.2 (2)	C13—N3—C14—C15	−15.3 (3)
C8—C3—C4—C5	−59.6 (2)	C13—N3—C14—C19	165.89 (18)
C3—C4—C5—C11	−59.9 (2)	N3—C14—C15—C16	−178.7 (2)
C3—C4—C5—C6	60.3 (2)	C19—C14—C15—C16	0.1 (3)
C4—C5—C6—C7	−60.4 (2)	C14—C15—C16—C17	0.9 (4)
C11—C5—C6—C7	59.5 (2)	C15—C16—C17—C18	−0.9 (4)
C5—C6—C7—C12	−60.2 (2)	C16—C17—C18—C19	0.0 (4)
C5—C6—C7—C8	60.7 (2)	C17—C18—C19—C14	1.0 (3)
C12—C7—C8—C3	60.39 (19)	N3—C14—C19—C18	177.80 (19)
C6—C7—C8—C3	−60.3 (2)	C15—C14—C19—C18	−1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S1i	0.87 (1)	2.62 (1)	3.4763 (19)	170 (2)
C13—H13A···Cg1ii	0.97	2.83	3.549 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯S1i	0.87 (1)	2.62 (1)	3.4763 (19)	170 (2)
C13—H13A⋯Cg1ii	0.97	2.83	3.549 (2)	132

Symmetry codes: (i) ; (ii) .