5-(Adamantan-1-yl)-3-[(2-meth-oxy-eth-yl)sulfan-yl]-4-phenyl-4H-1,2,4-triazole.

In the title adamantyl derivative, C(21)H(27)N(3)OS, the terminal meth-oxy-ethyl unit is disordered over two orientations with a refined site-occupancy ratio of 0.846 (6):0.154 (6). The 1,2,4-triazole ring is statistically planar [r.m.s. deviation = 0.002 (2) Å] and the phenyl substituent is almost perpendicular to its mean plane [dihedral angle = 83.57 (11)°]. No directional inter-molecular inter-actions were observed in the crystal structure.

Related literature

For the biological activity of adamantane derivatives, see: Kadi et al. (2010 ▶). For related adamantyl-1,2,4-triazole structures, see: Al-Abdullah et al. (2012 ▶); Almutairi et al. (2012 ▶); El-Emam et al. (2012 ▶). For substituted sulfanyl-1,2,4-triazole structures, see: Fun et al. (2011 ▶); Wang et al. (2011 ▶).

Experimental

Crystal data

C21H27N3OS

M = 369.53

Monoclinic,

a = 22.5107 (5) Å

b = 9.7642 (2) Å

c = 19.5594 (3) Å

β = 116.679 (1)°

V = 3841.43 (13) Å3

Z = 8

Cu Kα radiation

μ = 1.60 mm−1

T = 296 K

0.59 × 0.56 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.453, T max = 0.761

12922 measured reflections

3499 independent reflections

3075 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.130

S = 1.05

3499 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029510/hb6881sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029510/hb6881Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029510/hb6881Isup3.cml

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

C21H27N3OS	F(000) = 1584
Mr = 369.53	Dx = 1.278 Mg m−3
Monoclinic, C2/c	Melting point = 428–430 K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.54178 Å
a = 22.5107 (5) Å	Cell parameters from 3499 reflections
b = 9.7642 (2) Å	θ = 5.0–69.0°
c = 19.5594 (3) Å	µ = 1.60 mm−1
β = 116.679 (1)°	T = 296 K
V = 3841.43 (13) Å3	Plate, colorless
Z = 8	0.59 × 0.56 × 0.18 mm

Bruker SMART APEXII CCD diffractometer	3499 independent reflections
Radiation source: fine-focus sealed tube	3075 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 69.0°, θmin = 5.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −27→26
Tmin = 0.453, Tmax = 0.761	k = −11→11
12922 measured reflections	l = −23→23

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0809P)2 + 1.3248P] where P = (Fo2 + 2Fc2)/3
3499 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.30 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	Occ. (<1)
S1	0.08715 (2)	0.28171 (4)	0.23891 (2)	0.05409 (17)
N1	0.11945 (7)	0.33435 (13)	0.38845 (7)	0.0413 (3)
N2	0.10327 (8)	0.11543 (14)	0.35822 (9)	0.0532 (4)
N3	0.11921 (8)	0.13061 (14)	0.43546 (9)	0.0526 (4)
O1A	0.10717 (11)	0.1555 (2)	0.10375 (10)	0.0672 (7)	0.846 (6)
O1B	0.0543 (8)	0.1948 (10)	0.0738 (6)	0.076 (5)	0.154 (6)
C1	0.10350 (8)	0.23789 (17)	0.33203 (9)	0.0444 (4)
C2	0.12860 (8)	0.26011 (16)	0.45299 (9)	0.0424 (3)
C3	0.14495 (8)	0.31590 (16)	0.53129 (9)	0.0417 (3)
C4	0.13939 (12)	0.19832 (18)	0.58035 (11)	0.0593 (5)
H4A	0.0946	0.1616	0.5565	0.071*
H4B	0.1698	0.1254	0.5835	0.071*
C5	0.15593 (12)	0.2492 (2)	0.66116 (11)	0.0655 (5)
H5A	0.1524	0.1727	0.6916	0.079*
C6	0.10653 (11)	0.3612 (2)	0.65583 (11)	0.0627 (5)
H6A	0.0616	0.3249	0.6320	0.075*
H6B	0.1161	0.3931	0.7067	0.075*
C7	0.11237 (9)	0.47934 (19)	0.60849 (10)	0.0529 (4)
H7A	0.0812	0.5520	0.6053	0.063*
C8	0.09607 (8)	0.42908 (18)	0.52755 (9)	0.0463 (4)
H8A	0.0990	0.5050	0.4972	0.056*
H8B	0.0510	0.3938	0.5030	0.056*
C9	0.21600 (9)	0.3739 (2)	0.57084 (11)	0.0568 (4)
H9A	0.2475	0.3035	0.5738	0.068*
H9B	0.2201	0.4496	0.5411	0.068*
C10	0.23171 (9)	0.4233 (2)	0.65161 (11)	0.0649 (5)
H10A	0.2770	0.4604	0.6762	0.078*
C11	0.18282 (10)	0.5350 (2)	0.64632 (11)	0.0629 (5)
H11A	0.1932	0.5681	0.6972	0.076*
H11B	0.1866	0.6113	0.6167	0.076*
C12	0.22647 (12)	0.3049 (3)	0.69881 (11)	0.0755 (6)
H12A	0.2375	0.3359	0.7502	0.091*
H12B	0.2575	0.2333	0.7022	0.091*
C13	0.12558 (8)	0.47952 (16)	0.37871 (9)	0.0433 (4)
C14	0.18701 (10)	0.5351 (2)	0.39749 (12)	0.0607 (5)
H14A	0.2247	0.4800	0.4152	0.073*
C15	0.19180 (14)	0.6760 (2)	0.38947 (15)	0.0795 (7)
H15A	0.2331	0.7154	0.4022	0.095*
C16	0.13615 (16)	0.7570 (2)	0.36300 (13)	0.0793 (7)
H16A	0.1399	0.8511	0.3589	0.095*
C17	0.07556 (13)	0.6996 (2)	0.34282 (12)	0.0694 (6)
H17A	0.0379	0.7549	0.3241	0.083*
C18	0.06922 (10)	0.55996 (19)	0.34984 (10)	0.0544 (4)
H18A	0.0276	0.5210	0.3353	0.065*
C19	0.07046 (11)	0.1108 (2)	0.19793 (11)	0.0597 (5)
H19A	0.1092	0.0533	0.2248	0.072*
H19B	0.0337	0.0708	0.2040	0.072*
C20	0.05380 (13)	0.1161 (3)	0.11512 (13)	0.0738 (6)
H20A	0.0389	0.0263	0.0926	0.089*	0.846 (6)
H20B	0.0175	0.1800	0.0894	0.089*	0.846 (6)
H20C	0.0797	0.0424	0.1098	0.089*	0.154 (6)
H20D	0.0087	0.0837	0.0911	0.089*	0.154 (6)
C21	0.08943 (16)	0.1691 (3)	0.02410 (14)	0.0851 (7)
H21A	0.1278	0.1967	0.0183	0.128*	0.846 (6)
H21B	0.0552	0.2370	0.0017	0.128*	0.846 (6)
H21C	0.0735	0.0829	−0.0011	0.128*	0.846 (6)
H21D	0.0838	0.2477	−0.0077	0.128*	0.154 (6)
H21E	0.1359	0.1547	0.0565	0.128*	0.154 (6)
H21F	0.0711	0.0899	−0.0075	0.128*	0.154 (6)

	U11	U22	U33	U12	U13	U23
S1	0.0784 (3)	0.0442 (3)	0.0448 (3)	0.00191 (19)	0.0322 (2)	−0.00132 (15)
N1	0.0540 (7)	0.0328 (6)	0.0422 (7)	0.0010 (5)	0.0260 (6)	0.0000 (5)
N2	0.0774 (10)	0.0377 (7)	0.0523 (8)	−0.0018 (6)	0.0360 (8)	−0.0030 (6)
N3	0.0776 (10)	0.0362 (7)	0.0533 (8)	0.0003 (6)	0.0376 (8)	0.0005 (6)
O1A	0.0721 (14)	0.0758 (13)	0.0534 (10)	−0.0075 (10)	0.0280 (10)	−0.0151 (8)
O1B	0.123 (13)	0.055 (5)	0.065 (6)	0.010 (6)	0.056 (7)	0.022 (5)
C1	0.0529 (8)	0.0404 (8)	0.0449 (8)	0.0008 (6)	0.0263 (7)	−0.0019 (6)
C2	0.0520 (8)	0.0356 (8)	0.0456 (8)	0.0027 (6)	0.0272 (7)	0.0032 (6)
C3	0.0490 (8)	0.0377 (8)	0.0413 (8)	0.0026 (6)	0.0228 (7)	0.0023 (6)
C4	0.0881 (13)	0.0434 (9)	0.0560 (10)	0.0048 (9)	0.0408 (10)	0.0079 (8)
C5	0.0989 (16)	0.0556 (11)	0.0519 (10)	0.0053 (10)	0.0425 (11)	0.0125 (8)
C6	0.0718 (12)	0.0775 (13)	0.0489 (10)	−0.0054 (10)	0.0360 (9)	−0.0048 (9)
C7	0.0591 (10)	0.0553 (10)	0.0441 (9)	0.0095 (8)	0.0232 (8)	−0.0048 (7)
C8	0.0502 (8)	0.0471 (9)	0.0409 (8)	0.0059 (7)	0.0198 (7)	−0.0012 (6)
C9	0.0474 (9)	0.0705 (12)	0.0529 (10)	0.0028 (8)	0.0229 (8)	0.0019 (8)
C10	0.0480 (9)	0.0863 (14)	0.0494 (10)	−0.0035 (9)	0.0120 (8)	−0.0056 (9)
C11	0.0776 (12)	0.0604 (11)	0.0467 (10)	−0.0109 (9)	0.0242 (9)	−0.0126 (8)
C12	0.0768 (13)	0.0928 (16)	0.0453 (10)	0.0270 (12)	0.0172 (10)	0.0131 (10)
C13	0.0617 (9)	0.0335 (8)	0.0406 (8)	0.0006 (6)	0.0282 (7)	0.0013 (6)
C14	0.0665 (11)	0.0519 (10)	0.0701 (12)	−0.0058 (8)	0.0365 (10)	0.0029 (8)
C15	0.1005 (17)	0.0571 (13)	0.0889 (16)	−0.0289 (12)	0.0497 (14)	−0.0048 (11)
C16	0.141 (2)	0.0356 (9)	0.0696 (13)	−0.0053 (12)	0.0546 (15)	0.0023 (9)
C17	0.1080 (17)	0.0449 (10)	0.0599 (11)	0.0206 (11)	0.0419 (12)	0.0118 (8)
C18	0.0689 (11)	0.0469 (9)	0.0502 (9)	0.0084 (8)	0.0292 (8)	0.0051 (7)
C19	0.0726 (12)	0.0502 (10)	0.0541 (10)	−0.0017 (8)	0.0264 (9)	−0.0092 (8)
C20	0.0829 (15)	0.0723 (15)	0.0653 (13)	−0.0105 (11)	0.0325 (11)	−0.0228 (11)
C21	0.132 (2)	0.0667 (14)	0.0634 (13)	−0.0083 (14)	0.0501 (14)	−0.0103 (10)

S1—C1	1.7418 (17)	C9—H9B	0.9700
S1—C19	1.8161 (19)	C10—C12	1.517 (3)
N1—C1	1.370 (2)	C10—C11	1.519 (3)
N1—C2	1.389 (2)	C10—H10A	0.9800
N1—C13	1.4450 (19)	C11—H11A	0.9700
N2—C1	1.302 (2)	C11—H11B	0.9700
N2—N3	1.395 (2)	C12—H12A	0.9700
N3—C2	1.302 (2)	C12—H12B	0.9700
O1A—C20	1.371 (3)	C13—C14	1.374 (3)
O1A—C21	1.430 (3)	C13—C18	1.379 (2)
O1B—C20	1.119 (9)	C14—C15	1.394 (3)
O1B—C21	1.524 (11)	C14—H14A	0.9300
C2—C3	1.507 (2)	C15—C16	1.371 (4)
C3—C4	1.537 (2)	C15—H15A	0.9300
C3—C8	1.538 (2)	C16—C17	1.359 (4)
C3—C9	1.538 (2)	C16—H16A	0.9300
C4—C5	1.534 (3)	C17—C18	1.384 (3)
C4—H4A	0.9700	C17—H17A	0.9300
C4—H4B	0.9700	C18—H18A	0.9300
C5—C12	1.520 (3)	C19—C20	1.491 (3)
C5—C6	1.530 (3)	C19—H19A	0.9700
C5—H5A	0.9800	C19—H19B	0.9700
C6—C7	1.522 (3)	C20—H20A	0.9700
C6—H6A	0.9700	C20—H20B	0.9700
C6—H6B	0.9700	C20—H20C	0.9601
C7—C11	1.518 (3)	C20—H20D	0.9599
C7—C8	1.536 (2)	C21—H21A	0.9599
C7—H7A	0.9800	C21—H21B	0.9600
C8—H8A	0.9700	C21—H21C	0.9600
C8—H8B	0.9700	C21—H21D	0.9600
C9—C10	1.534 (3)	C21—H21E	0.9598
C9—H9A	0.9700	C21—H21F	0.9600
C1—S1—C19	98.08 (9)	C10—C12—H12B	109.9
C1—N1—C2	104.57 (13)	C5—C12—H12B	109.9
C1—N1—C13	125.03 (13)	H12A—C12—H12B	108.3
C2—N1—C13	130.39 (13)	C14—C13—C18	120.99 (16)
C1—N2—N3	106.50 (13)	C14—C13—N1	119.80 (15)
C2—N3—N2	108.70 (13)	C18—C13—N1	119.21 (15)
C20—O1A—C21	111.5 (2)	C13—C14—C15	118.7 (2)
C21—O1A—H20C	105.5	C13—C14—H14A	120.7
C20—O1A—H21E	146.8	C15—C14—H14A	120.7
H20C—O1A—H21E	117.0	C16—C15—C14	120.5 (2)
C20—O1B—C21	121.6 (9)	C16—C15—H15A	119.7
C20—O1B—H21B	152.8	C14—C15—H15A	119.7
N2—C1—N1	111.12 (14)	C17—C16—C15	120.0 (2)
N2—C1—S1	126.93 (13)	C17—C16—H16A	120.0
N1—C1—S1	121.95 (12)	C15—C16—H16A	120.0
N3—C2—N1	109.10 (14)	C16—C17—C18	120.8 (2)
N3—C2—C3	123.72 (14)	C16—C17—H17A	119.6
N1—C2—C3	127.16 (14)	C18—C17—H17A	119.6
C2—C3—C4	108.26 (13)	C13—C18—C17	119.01 (19)
C2—C3—C8	111.61 (13)	C13—C18—H18A	120.5
C4—C3—C8	108.03 (14)	C17—C18—H18A	120.5
C2—C3—C9	111.62 (13)	C20—C19—S1	110.44 (15)
C4—C3—C9	108.59 (15)	C20—C19—H19A	109.6
C8—C3—C9	108.64 (14)	S1—C19—H19A	109.6
C5—C4—C3	110.57 (15)	C20—C19—H19B	109.6
C5—C4—H4A	109.5	S1—C19—H19B	109.6
C3—C4—H4A	109.5	H19A—C19—H19B	108.1
C5—C4—H4B	109.5	O1B—C20—O1A	52.9 (7)
C3—C4—H4B	109.5	O1B—C20—C19	136.8 (6)
H4A—C4—H4B	108.1	O1A—C20—C19	112.00 (19)
C12—C5—C6	110.26 (19)	O1B—C20—H20A	114.0
C12—C5—C4	109.43 (18)	O1A—C20—H20A	109.2
C6—C5—C4	109.17 (17)	C19—C20—H20A	109.2
C12—C5—H5A	109.3	O1B—C20—H20B	57.4
C6—C5—H5A	109.3	O1A—C20—H20B	109.2
C4—C5—H5A	109.3	C19—C20—H20B	109.2
C7—C6—C5	108.95 (15)	H20A—C20—H20B	107.9
C7—C6—H6A	109.9	O1B—C20—H20C	103.5
C5—C6—H6A	109.9	O1A—C20—H20C	64.8
C7—C6—H6B	109.9	C19—C20—H20C	102.9
C5—C6—H6B	109.9	H20A—C20—H20C	51.4
H6A—C6—H6B	108.3	H20B—C20—H20C	146.7
C11—C7—C6	109.37 (16)	O1B—C20—H20D	103.0
C11—C7—C8	109.30 (15)	O1A—C20—H20D	145.4
C6—C7—C8	109.82 (15)	C19—C20—H20D	102.4
C11—C7—H7A	109.4	H20A—C20—H20D	53.6
C6—C7—H7A	109.4	H20B—C20—H20D	60.0
C8—C7—H7A	109.4	H20C—C20—H20D	105.0
C7—C8—C3	110.23 (13)	O1A—C21—H21A	109.3
C7—C8—H8A	109.6	O1B—C21—H21A	141.5
C3—C8—H8A	109.6	O1A—C21—H21B	109.6
C7—C8—H8B	109.6	O1B—C21—H21B	68.7
C3—C8—H8B	109.6	H21A—C21—H21B	109.5
H8A—C8—H8B	108.1	O1A—C21—H21C	109.6
C10—C9—C3	109.92 (15)	O1B—C21—H21C	106.9
C10—C9—H9A	109.7	H21A—C21—H21C	109.5
C3—C9—H9A	109.7	H21B—C21—H21C	109.5
C10—C9—H9B	109.7	O1A—C21—H21D	132.2
C3—C9—H9B	109.7	O1B—C21—H21D	109.1
H9A—C9—H9B	108.2	H21A—C21—H21D	64.1
C12—C10—C11	109.68 (18)	H21B—C21—H21D	46.1
C12—C10—C9	109.98 (19)	H21C—C21—H21D	117.2
C11—C10—C9	109.32 (15)	O1A—C21—H21E	65.1
C12—C10—H10A	109.3	O1B—C21—H21E	109.0
C11—C10—H10A	109.3	H21A—C21—H21E	49.2
C9—C10—H10A	109.3	H21B—C21—H21E	144.7
C7—C11—C10	110.02 (16)	H21C—C21—H21E	104.8
C7—C11—H11A	109.7	H21D—C21—H21E	109.5
C10—C11—H11A	109.7	O1A—C21—H21F	117.1
C7—C11—H11B	109.7	O1B—C21—H21F	110.3
C10—C11—H11B	109.7	H21A—C21—H21F	107.4
H11A—C11—H11B	108.2	H21B—C21—H21F	103.8
C10—C12—C5	109.14 (16)	H21D—C21—H21F	109.5
C10—C12—H12A	109.9	H21E—C21—H21F	109.5
C5—C12—H12A	109.9
C1—N2—N3—C2	−0.2 (2)	C2—C3—C9—C10	−177.38 (15)
N3—N2—C1—N1	0.5 (2)	C4—C3—C9—C10	−58.1 (2)
N3—N2—C1—S1	179.88 (13)	C8—C3—C9—C10	59.14 (19)
C2—N1—C1—N2	−0.63 (18)	C3—C9—C10—C12	60.3 (2)
C13—N1—C1—N2	178.41 (15)	C3—C9—C10—C11	−60.2 (2)
C2—N1—C1—S1	179.98 (12)	C6—C7—C11—C10	60.1 (2)
C13—N1—C1—S1	−1.0 (2)	C8—C7—C11—C10	−60.1 (2)
C19—S1—C1—N2	0.81 (19)	C12—C10—C11—C7	−60.1 (2)
C19—S1—C1—N1	−179.90 (14)	C9—C10—C11—C7	60.6 (2)
N2—N3—C2—N1	−0.18 (19)	C11—C10—C12—C5	59.3 (2)
N2—N3—C2—C3	178.35 (15)	C9—C10—C12—C5	−60.9 (2)
C1—N1—C2—N3	0.48 (17)	C6—C5—C12—C10	−59.7 (2)
C13—N1—C2—N3	−178.49 (16)	C4—C5—C12—C10	60.4 (2)
C1—N1—C2—C3	−177.99 (15)	C1—N1—C13—C14	−95.7 (2)
C13—N1—C2—C3	3.0 (3)	C2—N1—C13—C14	83.1 (2)
N3—C2—C3—C4	−7.1 (2)	C1—N1—C13—C18	83.7 (2)
N1—C2—C3—C4	171.18 (16)	C2—N1—C13—C18	−97.5 (2)
N3—C2—C3—C8	−125.84 (17)	C18—C13—C14—C15	2.3 (3)
N1—C2—C3—C8	52.4 (2)	N1—C13—C14—C15	−178.32 (18)
N3—C2—C3—C9	112.38 (18)	C13—C14—C15—C16	−0.3 (3)
N1—C2—C3—C9	−69.4 (2)	C14—C15—C16—C17	−1.4 (4)
C2—C3—C4—C5	179.69 (16)	C15—C16—C17—C18	1.1 (3)
C8—C3—C4—C5	−59.3 (2)	C14—C13—C18—C17	−2.6 (3)
C9—C3—C4—C5	58.3 (2)	N1—C13—C18—C17	178.02 (15)
C3—C4—C5—C12	−60.0 (2)	C16—C17—C18—C13	0.9 (3)
C3—C4—C5—C6	60.8 (2)	C1—S1—C19—C20	179.61 (15)
C12—C5—C6—C7	59.8 (2)	C21—O1B—C20—O1A	44.6 (9)
C4—C5—C6—C7	−60.4 (2)	C21—O1B—C20—C19	127.7 (7)
C5—C6—C7—C11	−59.5 (2)	C21—O1A—C20—O1B	−43.2 (7)
C5—C6—C7—C8	60.5 (2)	C21—O1A—C20—C19	−176.1 (2)
C11—C7—C8—C3	59.56 (19)	S1—C19—C20—O1B	8.4 (12)
C6—C7—C8—C3	−60.43 (19)	S1—C19—C20—O1A	67.0 (2)
C2—C3—C8—C7	177.63 (14)	C20—O1A—C21—O1B	34.6 (6)
C4—C3—C8—C7	58.74 (19)	C20—O1B—C21—O1A	−49.5 (9)
C9—C3—C8—C7	−58.88 (18)