N-(Adamantan-1-yl)-1,2,3,4-tetra­hydro­iso­quinoline-2-carbo­thio­amide

El-Emam, A.A.; Al-Abdullah, E.S.; Al-Tuwaijri, H.M.; Chidan Kumar, C.S.; Fun, H.-K.

doi:10.1107/S1600536813031516

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page o1815

doi:10.1107/S1600536813031516

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N-(Adamantan-1-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide

Ali A. El-Emam,^a ‡ Ebtehal S. Al-Abdullah,^a Hanaa M. Al-Tuwaijri,^a C. S. Chidan Kumar ^b and Hoong-Kun Fun ^a ^*§

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riaydh 11451, Saudi Arabia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hfun.c@ksu.edu.sa

(Received 18 November 2013; accepted 19 November 2013; online 23 November 2013)

In the title compound, C₂₀H₂₆N₂S, the N-containing six-membered ring adopts a boat conformation and the dihedral angle between the thiocarbamide group and the benzene ring is 49.67 (9)°. An intramolecular C—H⋯S hydrogen bond generates an S(6) ring motif. The N—H group is sterically hindered and there are no significant intermolecular interactions beyond van der Waals contacts.

CCDC reference: 972606

Related literature

For related structures and biological background, see: Al-Abdullah et al. (2012 ); El-Emam et al. (2012 ); Al-Tamimi et al. (2013 ).

Experimental

Crystal data

C₂₀H₂₆N₂S
M_r = 326.49
Monoclinic, P 2₁ /c
a = 19.1707 (5) Å
b = 6.4106 (2) Å
c = 14.2838 (3) Å
β = 103.366 (2)°
V = 1707.87 (8) Å³
Z = 4
Cu Kα radiation
μ = 1.67 mm⁻¹
T = 296 K
0.81 × 0.13 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.345, T_max = 0.921
10894 measured reflections
2831 independent reflections
2351 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.114
S = 1.07
2831 reflections
212 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯S1	0.97	2.72	3.365 (2)	125

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 ).

Supporting information

CCDC reference: 972606

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813031516/hb7163sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813031516/hb7163Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813031516/hb7163Isup3.cml

checkCIF report

Comment top

In continuation to our interest in the chemical and pharmacological properties of adamantane derivatives, (Al-Abdullah et al., 2012; El-Emam et al., 2012; Al-Tamimi et al., 2013) we synthesized the title compound (I) as a potential bioactive agent and its crystal structure is described here.

In the crystal structure of the title compound (I), the N-containing six-membered (N1/C1—C3/C8/C9) ring, Fig. 1, adopts a boat conformation, puckering parameters: Q = 0.639 (2) Å, θ = 88.01 (18)°, and ϕ = 119.18 (18)° with a maximum deviation of 0.380 (2) Å at atom C2. An intramolecular C–H···S hydrogen bond form a six-membered ring, Fig. 1, generating an S(6) ring motif, In the crystal structure, no significant intermolecular hydrogen bonds are observed.

Related literature top

For related structures and biological background, see: Al-Abdullah et al. (2012); El-Emam et al. (2012); Al-Tamimi et al. (2013).

Experimental top

A mixture of 387 mg 1-adamantylisothiocyanate (387 mg, 2 mmol) and 1,2,3,4-tetrahydroisoquinoline (266 mg, 2 mmol), in ethanol (15 ml), was heated under reflux for 2 h. On cooling, the precipitated crude product were filtered, washed with cold ethanol, dried, and crystallized from ethanol to yield 575 mg (88%) of the title compound (C₂₀H₂₆N₂S), m.p.: 420–422 K. Colorless needles were obtained from the slow evaporation of a CHCl₃:EtOH solution (1:1; 5 ml) at room temperature.

¹H NMR (CDCl₃, 500.13 MHz): δ 1.60–1.67 (m, 6H, Adamantane-H), 2.05 (s, 3H, Adamantane-H), 2.25–2.26 (m, 6H, Adamantane-H), 2.85 (t, 2H, J = 6.0 Hz, Isoquinoline-CH₂), 3.81 (t, 2H, J = 6.0 Hz, Isoquinoline-CH₂), 4.80 (s, 2H, Isoquinoline-CH₂), 5.15 (s, 1H, NH), 7.08–7.15 (m, 4H, Ar—H). ¹³C NMR (CDCl₃, 125.76 MHz): δ 29.68, 32.88, 35.56, 42.01 (Adamantane-C), 29.24, 48.12, 54.82, 126.49, 127.08, 128.33, 129.14, 133.43, 135.50 (Isoquinoline-C), 179.46 (C=S).

Computing details top

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

Figures top

Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids.

N-(Adamantan-1-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide top

Crystal data top

C₂₀H₂₆N₂S	F(000) = 704
M_r = 326.49	D_x = 1.270 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 2009 reflections
a = 19.1707 (5) Å	θ = 4.7–68.5°
b = 6.4106 (2) Å	µ = 1.67 mm⁻¹
c = 14.2838 (3) Å	T = 296 K
β = 103.366 (2)°	Needle, colorless
V = 1707.87 (8) Å³	0.81 × 0.13 × 0.05 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2831 independent reflections
Radiation source: fine-focus sealed tube	2351 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 65.0°, θ_min = 4.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −22→22
T_min = 0.345, T_max = 0.921	k = −5→7
10894 measured reflections	l = −16→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0467P)² + 0.4078P] where P = (F_o² + 2F_c²)/3
2831 reflections	(Δ/σ)_max = 0.001
212 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₀H₂₆N₂S	V = 1707.87 (8) Å³
M_r = 326.49	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 19.1707 (5) Å	µ = 1.67 mm⁻¹
b = 6.4106 (2) Å	T = 296 K
c = 14.2838 (3) Å	0.81 × 0.13 × 0.05 mm
β = 103.366 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2831 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2351 reflections with I > 2σ(I)
T_min = 0.345, T_max = 0.921	R_int = 0.040
10894 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.16 e Å⁻³
2831 reflections	Δρ_min = −0.20 e Å⁻³
212 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	0.28539 (3)	0.53707 (8)	0.87853 (4)	0.04780 (18)
N1	0.31695 (8)	0.8392 (2)	1.01049 (11)	0.0410 (4)
N2	0.22585 (9)	0.9145 (3)	0.88193 (13)	0.0487 (4)
C1	0.30653 (10)	1.0463 (3)	1.04991 (15)	0.0454 (5)
H1A	0.2582	1.0555	1.0596	0.054*
H1B	0.3118	1.1525	1.0037	0.054*
C2	0.35954 (10)	1.0889 (3)	1.14462 (14)	0.0468 (5)
H2A	0.3574	1.2352	1.1611	0.056*
H2B	0.3466	1.0071	1.1952	0.056*
C3	0.43444 (10)	1.0346 (3)	1.13817 (13)	0.0394 (4)
C4	0.49318 (11)	1.1642 (3)	1.16802 (14)	0.0477 (5)
H4A	0.4874	1.2961	1.1922	0.057*
C5	0.56065 (11)	1.0963 (4)	1.16170 (15)	0.0541 (6)
H5A	0.6002	1.1827	1.1819	0.065*
C6	0.56903 (11)	0.9017 (4)	1.12565 (15)	0.0549 (6)
H6A	0.6146	0.8556	1.1231	0.066*
C7	0.51028 (10)	0.7734 (3)	1.09301 (13)	0.0485 (5)
H7A	0.5162	0.6430	1.0674	0.058*
C8	0.44261 (10)	0.8406 (3)	1.09868 (13)	0.0388 (4)
C9	0.37639 (10)	0.7106 (3)	1.06543 (14)	0.0464 (5)
H9A	0.3863	0.5977	1.0252	0.056*
H9B	0.3626	0.6500	1.1207	0.056*
C10	0.27588 (9)	0.7748 (3)	0.92530 (14)	0.0386 (4)
C11	0.17921 (9)	0.9182 (3)	0.78351 (14)	0.0388 (4)
C12	0.13539 (11)	1.1194 (3)	0.77934 (17)	0.0559 (6)
H12A	0.1675	1.2379	0.7938	0.067*
H12B	0.1069	1.1140	0.8272	0.067*
C13	0.08603 (11)	1.1464 (3)	0.67914 (16)	0.0545 (6)
H13A	0.0589	1.2764	0.6773	0.065*
C14	0.03443 (11)	0.9647 (4)	0.65865 (17)	0.0556 (6)
H14A	0.0029	0.9802	0.5953	0.067*
H14B	0.0053	0.9610	0.7058	0.067*
C15	0.07696 (12)	0.7641 (3)	0.66319 (17)	0.0580 (6)
H15A	0.0437	0.6459	0.6497	0.070*
C16	0.12637 (10)	0.7366 (3)	0.76323 (15)	0.0491 (5)
H16A	0.0981	0.7328	0.8115	0.059*
H16B	0.1523	0.6060	0.7661	0.059*
C17	0.12141 (15)	0.7699 (4)	0.58855 (17)	0.0754 (8)
H17A	0.0902	0.7830	0.5249	0.090*
H17B	0.1483	0.6411	0.5908	0.090*
C18	0.17292 (14)	0.9540 (5)	0.60795 (19)	0.0727 (8)
H18A	0.2013	0.9586	0.5591	0.087*
C19	0.22293 (11)	0.9277 (4)	0.70823 (17)	0.0599 (6)
H19A	0.2506	0.8006	0.7101	0.072*
H19B	0.2560	1.0442	0.7215	0.072*
C20	0.13032 (13)	1.1555 (4)	0.6051 (2)	0.0729 (7)
H20A	0.1629	1.2734	0.6181	0.087*
H20B	0.0993	1.1740	0.5416	0.087*
H1N2	0.2278 (11)	1.034 (4)	0.9084 (15)	0.051 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0513 (3)	0.0321 (3)	0.0554 (4)	0.0024 (2)	0.0028 (2)	−0.0036 (2)
N1	0.0388 (8)	0.0340 (9)	0.0481 (10)	0.0010 (6)	0.0057 (7)	−0.0023 (7)
N2	0.0455 (9)	0.0361 (11)	0.0575 (11)	0.0066 (7)	−0.0024 (8)	−0.0109 (8)
C1	0.0437 (11)	0.0419 (12)	0.0509 (12)	0.0046 (8)	0.0117 (9)	−0.0049 (8)
C2	0.0508 (12)	0.0453 (12)	0.0451 (12)	0.0021 (9)	0.0126 (9)	−0.0060 (9)
C3	0.0456 (11)	0.0434 (12)	0.0290 (10)	−0.0016 (8)	0.0082 (8)	0.0022 (7)
C4	0.0589 (12)	0.0463 (12)	0.0359 (11)	−0.0082 (9)	0.0067 (9)	−0.0005 (8)
C5	0.0464 (12)	0.0705 (16)	0.0440 (12)	−0.0172 (11)	0.0076 (10)	0.0007 (10)
C6	0.0420 (11)	0.0819 (17)	0.0419 (12)	0.0021 (11)	0.0121 (9)	0.0031 (11)
C7	0.0528 (12)	0.0557 (13)	0.0363 (11)	0.0108 (10)	0.0088 (9)	−0.0016 (9)
C8	0.0430 (10)	0.0406 (11)	0.0309 (10)	0.0017 (8)	0.0049 (8)	0.0020 (7)
C9	0.0493 (11)	0.0363 (11)	0.0490 (12)	0.0027 (9)	0.0020 (9)	0.0021 (8)
C10	0.0336 (9)	0.0353 (10)	0.0472 (12)	−0.0029 (7)	0.0101 (8)	0.0012 (8)
C11	0.0333 (9)	0.0306 (10)	0.0501 (12)	0.0003 (7)	0.0046 (8)	−0.0002 (8)
C12	0.0495 (12)	0.0392 (13)	0.0717 (15)	0.0064 (9)	−0.0010 (11)	−0.0092 (10)
C13	0.0521 (12)	0.0348 (12)	0.0698 (15)	0.0127 (9)	0.0002 (11)	0.0022 (9)
C14	0.0413 (11)	0.0607 (15)	0.0593 (14)	0.0029 (9)	0.0004 (10)	0.0047 (10)
C15	0.0582 (13)	0.0365 (13)	0.0661 (15)	−0.0082 (10)	−0.0124 (11)	0.0015 (10)
C16	0.0454 (11)	0.0386 (12)	0.0587 (13)	−0.0052 (9)	0.0024 (9)	0.0102 (9)
C17	0.1000 (19)	0.0659 (18)	0.0500 (15)	0.0366 (15)	−0.0034 (14)	−0.0084 (11)
C18	0.0681 (16)	0.098 (2)	0.0596 (16)	0.0250 (14)	0.0300 (13)	0.0246 (14)
C19	0.0428 (11)	0.0660 (16)	0.0751 (16)	0.0084 (10)	0.0219 (11)	0.0182 (12)
C20	0.0663 (15)	0.0633 (17)	0.0850 (18)	0.0017 (12)	0.0093 (14)	0.0356 (13)

Geometric parameters (Å, º) top

S1—C10	1.6906 (19)	C11—C16	1.526 (2)
N1—C10	1.352 (2)	C11—C12	1.533 (3)
N1—C1	1.473 (2)	C12—C13	1.532 (3)
N1—C9	1.477 (2)	C12—H12A	0.9700
N2—C10	1.353 (2)	C12—H12B	0.9700
N2—C11	1.482 (2)	C13—C20	1.503 (3)
N2—H1N2	0.85 (2)	C13—C14	1.512 (3)
C1—C2	1.517 (3)	C13—H13A	0.9800
C1—H1A	0.9700	C14—C15	1.516 (3)
C1—H1B	0.9700	C14—H14A	0.9700
C2—C3	1.501 (3)	C14—H14B	0.9700
C2—H2A	0.9700	C15—C17	1.511 (4)
C2—H2B	0.9700	C15—C16	1.531 (3)
C3—C4	1.385 (3)	C15—H15A	0.9800
C3—C8	1.389 (3)	C16—H16A	0.9700
C4—C5	1.387 (3)	C16—H16B	0.9700
C4—H4A	0.9300	C17—C18	1.522 (4)
C5—C6	1.373 (3)	C17—H17A	0.9700
C5—H5A	0.9300	C17—H17B	0.9700
C6—C7	1.385 (3)	C18—C20	1.524 (4)
C6—H6A	0.9300	C18—C19	1.538 (3)
C7—C8	1.387 (3)	C18—H18A	0.9800
C7—H7A	0.9300	C19—H19A	0.9700
C8—C9	1.501 (3)	C19—H19B	0.9700
C9—H9A	0.9700	C20—H20A	0.9700
C9—H9B	0.9700	C20—H20B	0.9700
C11—C19	1.510 (3)

C10—N1—C1	121.12 (15)	C13—C12—H12A	109.6
C10—N1—C9	121.67 (16)	C11—C12—H12B	109.6
C1—N1—C9	117.13 (15)	C13—C12—H12B	109.6
C10—N2—C11	130.81 (17)	H12A—C12—H12B	108.1
C10—N2—H1N2	116.1 (15)	C20—C13—C14	110.2 (2)
C11—N2—H1N2	111.1 (15)	C20—C13—C12	109.55 (18)
N1—C1—C2	112.39 (16)	C14—C13—C12	109.20 (18)
N1—C1—H1A	109.1	C20—C13—H13A	109.3
C2—C1—H1A	109.1	C14—C13—H13A	109.3
N1—C1—H1B	109.1	C12—C13—H13A	109.3
C2—C1—H1B	109.1	C13—C14—C15	108.90 (17)
H1A—C1—H1B	107.9	C13—C14—H14A	109.9
C3—C2—C1	110.89 (16)	C15—C14—H14A	109.9
C3—C2—H2A	109.5	C13—C14—H14B	109.9
C1—C2—H2A	109.5	C15—C14—H14B	109.9
C3—C2—H2B	109.5	H14A—C14—H14B	108.3
C1—C2—H2B	109.5	C17—C15—C14	109.51 (19)
H2A—C2—H2B	108.0	C17—C15—C16	109.45 (18)
C4—C3—C8	120.13 (18)	C14—C15—C16	110.37 (19)
C4—C3—C2	124.29 (18)	C17—C15—H15A	109.2
C8—C3—C2	115.58 (17)	C14—C15—H15A	109.2
C3—C4—C5	119.7 (2)	C16—C15—H15A	109.2
C3—C4—H4A	120.1	C11—C16—C15	109.25 (16)
C5—C4—H4A	120.1	C11—C16—H16A	109.8
C6—C5—C4	120.06 (19)	C15—C16—H16A	109.8
C6—C5—H5A	120.0	C11—C16—H16B	109.8
C4—C5—H5A	120.0	C15—C16—H16B	109.8
C5—C6—C7	120.60 (19)	H16A—C16—H16B	108.3
C5—C6—H6A	119.7	C15—C17—C18	109.80 (19)
C7—C6—H6A	119.7	C15—C17—H17A	109.7
C6—C7—C8	119.6 (2)	C18—C17—H17A	109.7
C6—C7—H7A	120.2	C15—C17—H17B	109.7
C8—C7—H7A	120.2	C18—C17—H17B	109.7
C7—C8—C3	119.76 (18)	H17A—C17—H17B	108.2
C7—C8—C9	122.91 (18)	C17—C18—C20	109.3 (2)
C3—C8—C9	117.32 (16)	C17—C18—C19	108.9 (2)
N1—C9—C8	110.52 (16)	C20—C18—C19	109.4 (2)
N1—C9—H9A	109.5	C17—C18—H18A	109.7
C8—C9—H9A	109.5	C20—C18—H18A	109.7
N1—C9—H9B	109.5	C19—C18—H18A	109.7
C8—C9—H9B	109.5	C11—C19—C18	109.80 (17)
H9A—C9—H9B	108.1	C11—C19—H19A	109.7
N1—C10—N2	114.44 (17)	C18—C19—H19A	109.7
N1—C10—S1	122.50 (14)	C11—C19—H19B	109.7
N2—C10—S1	123.05 (15)	C18—C19—H19B	109.7
N2—C11—C19	111.34 (16)	H19A—C19—H19B	108.2
N2—C11—C16	113.34 (16)	C13—C20—C18	109.52 (18)
C19—C11—C16	110.43 (18)	C13—C20—H20A	109.8
N2—C11—C12	104.80 (16)	C18—C20—H20A	109.8
C19—C11—C12	109.13 (17)	C13—C20—H20B	109.8
C16—C11—C12	107.50 (16)	C18—C20—H20B	109.8
C11—C12—C13	110.23 (17)	H20A—C20—H20B	108.2
C11—C12—H12A	109.6

C10—N1—C1—C2	−178.44 (16)	C10—N2—C11—C12	−179.4 (2)
C9—N1—C1—C2	−1.5 (2)	N2—C11—C12—C13	178.19 (16)
N1—C1—C2—C3	47.4 (2)	C19—C11—C12—C13	58.8 (2)
C1—C2—C3—C4	131.5 (2)	C16—C11—C12—C13	−60.9 (2)
C1—C2—C3—C8	−48.2 (2)	C11—C12—C13—C20	−59.5 (2)
C8—C3—C4—C5	−2.4 (3)	C11—C12—C13—C14	61.2 (2)
C2—C3—C4—C5	177.96 (19)	C20—C13—C14—C15	60.7 (2)
C3—C4—C5—C6	0.2 (3)	C12—C13—C14—C15	−59.6 (2)
C4—C5—C6—C7	1.7 (3)	C13—C14—C15—C17	−60.3 (2)
C5—C6—C7—C8	−1.4 (3)	C13—C14—C15—C16	60.2 (2)
C6—C7—C8—C3	−0.8 (3)	N2—C11—C16—C15	175.54 (16)
C6—C7—C8—C9	−179.65 (18)	C19—C11—C16—C15	−58.8 (2)
C4—C3—C8—C7	2.7 (3)	C12—C11—C16—C15	60.2 (2)
C2—C3—C8—C7	−177.63 (17)	C17—C15—C16—C11	59.4 (2)
C4—C3—C8—C9	−178.40 (17)	C14—C15—C16—C11	−61.2 (2)
C2—C3—C8—C9	1.2 (3)	C14—C15—C17—C18	60.0 (2)
C10—N1—C9—C8	133.07 (17)	C16—C15—C17—C18	−61.1 (2)
C1—N1—C9—C8	−43.8 (2)	C15—C17—C18—C20	−58.9 (3)
C7—C8—C9—N1	−136.37 (18)	C15—C17—C18—C19	60.6 (2)
C3—C8—C9—N1	44.8 (2)	N2—C11—C19—C18	−174.24 (19)
C1—N1—C10—N2	−0.3 (3)	C16—C11—C19—C18	58.9 (2)
C9—N1—C10—N2	−177.09 (16)	C12—C11—C19—C18	−59.0 (2)
C1—N1—C10—S1	−179.06 (14)	C17—C18—C19—C11	−59.3 (3)
C9—N1—C10—S1	4.2 (2)	C20—C18—C19—C11	60.2 (3)
C11—N2—C10—N1	169.16 (18)	C14—C13—C20—C18	−60.1 (3)
C11—N2—C10—S1	−12.1 (3)	C12—C13—C20—C18	60.0 (3)
C10—N2—C11—C19	−61.5 (3)	C17—C18—C20—C13	58.8 (3)
C10—N2—C11—C16	63.7 (3)	C19—C18—C20—C13	−60.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···S1	0.97	2.72	3.365 (2)	125

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···S1	0.97	2.72	3.365 (2)	125

Footnotes

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

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center for Female Scientific and Medical Colleges, King Saud University, is greatly appreciated. CSCK thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

References

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