5-(Adamantan-1-yl)-3-anilinomethyl-2,3-di­hydro-1,3,4-oxa­diazole-2-thione

Al-Tamimi, A.-M.S.; Al-Deeb, O.A.; El-Emam, A.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536813009835

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o729

https://doi.org/10.1107/S1600536813009835

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5-(Adamantan-1-yl)-3-anilinomethyl-2,3-dihydro-1,3,4-oxadiazole-2-thione

Abdul-Malek S. Al-Tamimi,^a Omar A. Al-Deeb,^b Ali A. El-Emam,^b ‡ Seik Weng Ng ^c,^d and Edward R. T. Tiekink ^c ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, Salman bin Abdulaziz University, Alkharj 11942, Saudi Arabia, ^bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 8 April 2013; accepted 10 April 2013; online 13 April 2013)

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

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_r = 341.46
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.131
S = 1.03
4115 reflections
221 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+2.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813009835/hb7068sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009835/hb7068Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813009835/hb7068Isup3.cml

checkCIF report

Comment top

In continuation of our long-term interest in the chemical and pharmacological properties of adamantane derivatives (El-Emam & Ibrahim, 1991; El-Emam et al., 2004), including structural studies (Al-Tamimi et al., 2013), we describe herein the X-ray crystal structure determination of the title compound, (I).

In (I), Fig. 1, the oxadiazole ring is strictly planar (r.m.s. deviation = 0.003 Å) and the thione-S1 atom lies in this plane. The benzene ring is highly twisted out of this plane, forming a dihedral angle of 50.30 (11)°; the N2—N1—C13—N3 torsion angle = -101.2 (2)°. Despite the kink in the molecule, the thione-S1 and amine-N3—H atoms are syn, as seen in the S1—C1···N3—H3 torsion angle of 3 (1)°. This allows for the formation of N—H···S hydrogen bonds that lead to helical supramolecular chains along the b axis, Fig. 2 and Table 1. Chains are connected into layers parallel to (101) by methylene-C—H···π(phenyl) interactions, Fig. 3 and Table 1.

Related literature top

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 top

A mixture of 5-(adamantane-1-yl)-1,3,4-oxadiazole-2-thiol (2.36 g, 0.01 mol), aniline (0.93 g, 0.01 mol) and 37% formaldehyde solution (1.5 ml), in ethanol (15 ml), was stirred at room temperature for 2 h and allowed to stand overnight. The precipitated crude product was filtered, washed with water, dried, and crystallized from ethanol to yield 3.04 g (89%) of the title compound (I) as fine colourless crystals. M.pt: 439–471 K. Colourless prisms were obtained by slow evaporation of its CHCl₃-ethanol (1:1; 10 ml) solution held at room temperature. ¹H NMR (CDCl₃, 500.13 MHz): δ 1.75 (q, 6H, adamantane-H), 2.01 (s, 6H, adamantane-H), 2.12 (s, 3H, adamantane-H), 2.98 (t, 4H, piperazine-H), 3.20 (t, 4H, piperazine-H), 5.06 (s, 2H, CH₂), 6.88–6.95 (m, 3H, Ar—H), 7.27 (t, 2H, Ar—H, J = 7.5 Hz). ¹³C NMR (CDCl₃, 125.76 MHz): δ 27.47, 34.40, 36.10, 39.12 (adamantane-C), 49.36, 50.26 (piperazine-C), 69.86 (CH₂), 116.43, 120.15, 129.17, 151.22 (Ar—C), 167.91 (C═N), 178.62 (C═S).

Structure description top

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).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 35% probability level.
	Fig. 2. A view of the helical supramolecular chain along the b axis in (I), which is sustained by N—H···S hydrogen bonds shown as orange dashed lines.
	Fig. 3. View of the unit-cell contents in projection down the b axis of (I). The N—H···S and C—H···π interactions are shown as orange and purple dashed lines, respectively.

5-(Adamantan-1-yl)-3-anilinomethyl-2,3-dihydro-1,3,4-oxadiazole-2-thione top

Crystal data top

C₁₉H₂₃N₃OS	F(000) = 728
M_r = 341.46	D_x = 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

Data collection top

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	R_int = 0.033
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 3.0°
ω scan	h = −16→18
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −7→9
T_min = 0.863, T_max = 1.000	l = −23→22
12073 measured reflections

Refinement top

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(F_o²) + (0.0529P)² + 0.3647P] where P = (F_o² + 2F_c²)/3
4115 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.27 e Å⁻³
1 restraint	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₉H₂₃N₃OS	V = 1780.2 (3) Å³
M_r = 341.46	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.1326 (13) Å	µ = 0.19 mm⁻¹
b = 7.1179 (5) Å	T = 295 K
c = 18.3685 (16) Å	0.40 × 0.30 × 0.20 mm
β = 105.546 (10)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4115 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2827 reflections with I > 2σ(I)
T_min = 0.863, T_max = 1.000	R_int = 0.033
12073 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	1 restraint
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.27 e Å⁻³
4115 reflections	Δρ_min = −0.21 e Å⁻³
221 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₃N₃OS
M_r	341.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	14.1326 (13), 7.1179 (5), 18.3685 (16)
β (°)	105.546 (10)
V (Å³)	1780.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.863, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12073, 4115, 2827
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.131, 1.03
No. of reflections	4115
No. of parameters	221
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.21

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S1ⁱ	0.872 (10)	2.615 (10)	3.4763 (19)	169.7 (18)
C13—H13A···Cg1ⁱⁱ	0.97	2.83	3.549 (2)	132

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+2.

Footnotes

‡Additional correspondence author, e-mail: elemam5@hotmail.com.

Acknowledgements

The financial support of the Deanship of Scientific Research, Salman bin Abdulaziz University, Alkharj, Saudi Arabia, is greatly appreciated. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Al-Tamimi, A.-M. S., Alafeefy, A. M., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o730. CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107-5113. Web of Science CrossRef PubMed CAS Google Scholar
El-Emam, A. A. & Ibrahim, T. M. (1991). Arzneim. Forsch. Drug. Res. 41, 1260–1264. CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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