9-Benzyl-6-benzyl­sulfanyl-9H-purin-2-amine

Hariono, M.; Wahab, H.A.; Tan, M.L.; Rosli, M.M.; Razak, I.A.

doi:10.1107/S1600536814001986

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Page o288

doi:10.1107/S1600536814001986

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9-Benzyl-6-benzylsulfanyl-9H-purin-2-amine

Maywan Hariono,^a Habibah A. Wahab,^a,^b ‡ Mei Lan Tan,^b Mohd Mustaqim Rosli ^c and Ibrahim Abdul Razak ^c ^*§

^aPharmaceutical Design and Simulation (PhDs) Laboratory, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia, ^bMalaysian Institute of Pharmaceuticals and Nutraceuticals, Ministry of Science Technology and Inovation, 11700 Halaman Bukit Gambir, Pulau Pinang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 19 December 2013; accepted 28 January 2014; online 12 February 2014)

In the title compound, C₁₉H₁₇N₅S, the dihedral angles between the purine ring system (r.m.s. deviation = 0.009 Å) and the S-bound and methylene-bound phenyl rings are 74.67 (8) and 71.28 (7)°, respectively. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds generate R₂²(8) loops. C—H⋯N interactions link the dimers into (100) sheets.

CCDC reference: 983914

Related literature

For background to the biological activity of thiopurine derivatives, see: Hadda et al. (2009 ); Nguyen et al. (2009 ). For further synthetic details, see: Banh et al. (2011 ); Salvatore et al. (2002 , 2005 ).

Experimental

Crystal data

C₁₉H₁₇N₅S
M_r = 347.44
Monoclinic, P 2₁ /c
a = 16.7346 (7) Å
b = 5.5511 (3) Å
c = 20.4817 (10) Å
β = 121.325 (3)°
V = 1625.31 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.69 × 0.19 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.868, T_max = 0.972
16728 measured reflections
4956 independent reflections
3416 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.137
S = 1.06
4956 reflections
234 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H1N5⋯N3ⁱ	0.91 (3)	2.14 (3)	3.040 (3)	173 (2)
C7—H7B⋯N3ⁱⁱ	0.99	2.57	3.548 (2)	172
C8—H8A⋯N2ⁱⁱⁱ	0.95	2.39	3.274 (2)	155
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+2, -z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: 983914

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814001986/hb7176sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814001986/hb7176Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814001986/hb7176Isup3.cml

checkCIF report

Introduction top

Thiopurine and its analogues possess a broad pharmacological activity for example as a cytotoxic agent (Nguyen et al., 2009) and in the treatment of lupus nephritis (Hadda et al., 2009). As part of our studies in this area, we report the synthesis and structure of the title compound.

Experimental top

The method to synthesize the title compound was modified from a few papers (Banh et al., 2011; Salvatore et al., 2002; Salvatore et al., 2005). 2-amino-9H-purine-6-thiol (0.598 mmol) was mixed with cesium carbonate (0.598 mmol) in 3.5 ml of dimethylformamide and then stirred vigorously for 15 minutes. Another mixture containing benzyl bromide (1.315 mmol), tetrabutylammonium iodide (0.598 mmol) in 3.5 ml of DMF was added to the first mixture and the stirring was continued at room temperature for six hours. The reaction progress was monitored by TLC using n-hexane:ethyl acetate (0.5:3.5) as a solvent. After the product being formed, the reaction mixture was diluted with 70 mL of water and then extracted using 3 × 70 ml of ethyl acetate. The organic phase was collected, washed with 3× 70 ml of water and then dried over anhydrous magnesium sulfate. This organic phase was then evaporated in vacuo and the crude product was re-crystallized from a hot methanol to afford the title compound as colourless blocks.

Refinement top

N bound H atoms were located from difference Fourier maps and freely refined. The remaining H atoms were positioned geometrically and refined using a riding model with with C–H = 0.95–0.99 Å and U_iso(H) = 1.2U_eq(C).

Results and discussion top

The purin ring is almost planar with the maximum deviation of 0.014 (2)Å at atom C11. It makes a dihedral angle of 71.28 and 74.67 (8)° with the two benzene rings, C1—C6 and C14—C19, respectively and these two benzene rings make a dihedral angle of 76.04)10)° with each other (Fig. 1).

In the crytsal structure, two dimers involving N5—H1N5···N3ⁱ and C7—H7B···N3ⁱⁱ are observed. These two dimers formed stacked molecules down the b-axis. Intermolecular interactions of C8—H8A···N2ⁱⁱⁱ further expand the molecules into infinite layers parallel to the bc-plane (Fig. 2).

Related literature top

For background to the biological activity of thiopurine derivatives, see: Hadda et al. (2009); Nguyen et al. (2009). For further synthetic details, see: Banh et al. (2011); Salvatore et al. (2002, 2005).

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 asymmetric unit of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of (I). Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.

9-Benzyl-6-benzylsulfanyl-9H-purin-2-amine top

Crystal data top

C₁₉H₁₇N₅S	F(000) = 728
M_r = 347.44	D_x = 1.420 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3425 reflections
a = 16.7346 (7) Å	θ = 2.3–30.0°
b = 5.5511 (3) Å	µ = 0.21 mm⁻¹
c = 20.4817 (10) Å	T = 100 K
β = 121.325 (3)°	Block, colourless
V = 1625.31 (14) Å³	0.69 × 0.19 × 0.14 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4956 independent reflections
Radiation source: fine-focus sealed tube	3416 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
φ and ω scans	θ_max = 30.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −23→23
T_min = 0.868, T_max = 0.972	k = −7→7
16728 measured reflections	l = −25→29

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0602P)² + 0.4349P] where P = (F_o² + 2F_c²)/3
4956 reflections	(Δ/σ)_max < 0.001
234 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

C₁₉H₁₇N₅S	V = 1625.31 (14) Å³
M_r = 347.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.7346 (7) Å	µ = 0.21 mm⁻¹
b = 5.5511 (3) Å	T = 100 K
c = 20.4817 (10) Å	0.69 × 0.19 × 0.14 mm
β = 121.325 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4956 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3416 reflections with I > 2σ(I)
T_min = 0.868, T_max = 0.972	R_int = 0.048
16728 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.33 e Å⁻³
4956 reflections	Δρ_min = −0.58 e Å⁻³
234 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	0.24764 (3)	0.72454 (8)	0.12637 (3)	0.01824 (13)
N1	0.52964 (10)	1.0733 (3)	0.14394 (8)	0.0147 (3)
N2	0.42255 (10)	1.0996 (3)	0.17932 (8)	0.0169 (3)
N3	0.47003 (10)	0.7208 (3)	0.06126 (8)	0.0148 (3)
N4	0.32973 (10)	0.5624 (3)	0.05291 (8)	0.0151 (3)
N5	0.39014 (11)	0.3896 (3)	−0.01293 (9)	0.0183 (3)
C1	0.70179 (12)	0.7950 (3)	0.20967 (10)	0.0170 (4)
H1A	0.6619	0.7724	0.2293	0.020*
C2	0.77591 (13)	0.6376 (3)	0.23027 (10)	0.0200 (4)
H2A	0.7865	0.5080	0.2642	0.024*
C3	0.83454 (13)	0.6682 (4)	0.20170 (10)	0.0211 (4)
H3A	0.8838	0.5570	0.2147	0.025*
C4	0.82082 (13)	0.8621 (3)	0.15408 (10)	0.0210 (4)
H4A	0.8617	0.8863	0.1355	0.025*
C5	0.74731 (12)	1.0206 (3)	0.13374 (10)	0.0190 (4)
H5A	0.7385	1.1538	0.1016	0.023*
C6	0.68604 (12)	0.9858 (3)	0.16023 (9)	0.0154 (3)
C7	0.60378 (12)	1.1554 (3)	0.13203 (10)	0.0176 (4)
H7A	0.6271	1.3124	0.1581	0.021*
H7B	0.5767	1.1826	0.0767	0.021*
C8	0.49754 (13)	1.1938 (3)	0.18504 (10)	0.0165 (4)
H8A	0.5274	1.3330	0.2149	0.020*
C9	0.46824 (11)	0.8869 (3)	0.10795 (9)	0.0133 (3)
C10	0.39805 (12)	0.5647 (3)	0.03571 (9)	0.0144 (3)
C11	0.33280 (12)	0.7292 (3)	0.10083 (9)	0.0138 (3)
C12	0.40253 (12)	0.9046 (3)	0.13023 (9)	0.0141 (3)
C13	0.19169 (13)	0.4383 (3)	0.08654 (10)	0.0186 (4)
H13A	0.2409	0.3215	0.0950	0.022*
H13B	0.1636	0.3806	0.1160	0.022*
C14	0.11669 (12)	0.4322 (3)	0.00268 (10)	0.0166 (4)
C15	0.10259 (13)	0.6128 (3)	−0.04927 (10)	0.0198 (4)
H15A	0.1421	0.7504	−0.0327	0.024*
C16	0.03108 (13)	0.5934 (3)	−0.12532 (11)	0.0221 (4)
H16A	0.0219	0.7190	−0.1601	0.027*
C17	−0.02712 (13)	0.3932 (3)	−0.15127 (11)	0.0217 (4)
H17A	−0.0761	0.3812	−0.2033	0.026*
C18	−0.01235 (13)	0.2113 (3)	−0.09980 (11)	0.0217 (4)
H18A	−0.0512	0.0726	−0.1168	0.026*
C19	0.05850 (13)	0.2296 (3)	−0.02383 (11)	0.0196 (4)
H19A	0.0677	0.1032	0.0107	0.023*
H1N5	0.4310 (15)	0.370 (4)	−0.0289 (12)	0.030 (6)*
H2N5	0.3390 (15)	0.304 (4)	−0.0358 (12)	0.024 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0183 (2)	0.0203 (2)	0.0209 (2)	−0.00120 (18)	0.0136 (2)	−0.00239 (18)
N1	0.0136 (7)	0.0158 (7)	0.0139 (7)	−0.0025 (6)	0.0066 (6)	−0.0020 (6)
N2	0.0205 (8)	0.0153 (7)	0.0157 (7)	0.0009 (6)	0.0100 (6)	−0.0001 (6)
N3	0.0160 (7)	0.0152 (7)	0.0150 (7)	−0.0017 (6)	0.0095 (6)	−0.0013 (6)
N4	0.0148 (7)	0.0163 (7)	0.0158 (7)	0.0013 (6)	0.0090 (6)	−0.0001 (6)
N5	0.0161 (8)	0.0203 (8)	0.0209 (8)	−0.0053 (7)	0.0113 (7)	−0.0083 (6)
C1	0.0161 (9)	0.0189 (9)	0.0148 (8)	−0.0039 (7)	0.0072 (7)	−0.0020 (7)
C2	0.0188 (9)	0.0186 (9)	0.0177 (9)	−0.0028 (7)	0.0061 (7)	−0.0005 (7)
C3	0.0174 (9)	0.0218 (9)	0.0200 (9)	0.0004 (7)	0.0067 (8)	−0.0035 (7)
C4	0.0183 (9)	0.0238 (10)	0.0231 (9)	−0.0039 (8)	0.0121 (8)	−0.0046 (8)
C5	0.0203 (9)	0.0188 (9)	0.0176 (8)	−0.0052 (7)	0.0097 (8)	−0.0025 (7)
C6	0.0151 (9)	0.0153 (8)	0.0140 (8)	−0.0039 (7)	0.0062 (7)	−0.0047 (6)
C7	0.0180 (9)	0.0156 (8)	0.0214 (9)	−0.0016 (7)	0.0117 (8)	0.0005 (7)
C8	0.0214 (9)	0.0140 (8)	0.0140 (8)	−0.0004 (7)	0.0092 (7)	−0.0013 (6)
C9	0.0140 (8)	0.0134 (8)	0.0107 (7)	0.0003 (6)	0.0051 (6)	0.0004 (6)
C10	0.0148 (8)	0.0141 (8)	0.0142 (8)	0.0004 (7)	0.0074 (7)	0.0006 (6)
C11	0.0134 (8)	0.0149 (8)	0.0129 (8)	0.0017 (6)	0.0066 (7)	0.0026 (6)
C12	0.0165 (8)	0.0131 (8)	0.0139 (8)	0.0007 (7)	0.0088 (7)	0.0002 (6)
C13	0.0196 (9)	0.0171 (9)	0.0222 (9)	−0.0022 (7)	0.0129 (8)	0.0012 (7)
C14	0.0133 (8)	0.0187 (9)	0.0196 (8)	−0.0001 (7)	0.0099 (7)	−0.0001 (7)
C15	0.0189 (9)	0.0178 (9)	0.0241 (9)	0.0003 (7)	0.0122 (8)	0.0008 (7)
C16	0.0227 (10)	0.0212 (9)	0.0225 (9)	0.0048 (8)	0.0118 (8)	0.0056 (8)
C17	0.0168 (9)	0.0252 (10)	0.0194 (9)	0.0033 (8)	0.0068 (7)	0.0007 (8)
C18	0.0180 (9)	0.0203 (9)	0.0268 (10)	−0.0015 (7)	0.0117 (8)	−0.0013 (8)
C19	0.0184 (9)	0.0187 (9)	0.0235 (9)	0.0003 (7)	0.0122 (8)	0.0017 (7)

Geometric parameters (Å, º) top

S1—C11	1.7551 (17)	C5—C6	1.400 (2)
S1—C13	1.8091 (18)	C5—H5A	0.9500
N1—C9	1.372 (2)	C6—C7	1.513 (2)
N1—C8	1.384 (2)	C7—H7A	0.9900
N1—C7	1.456 (2)	C7—H7B	0.9900
N2—C8	1.307 (2)	C8—H8A	0.9500
N2—C12	1.395 (2)	C9—C12	1.396 (2)
N3—C9	1.340 (2)	C11—C12	1.393 (2)
N3—C10	1.349 (2)	C13—C14	1.512 (2)
N4—C11	1.331 (2)	C13—H13A	0.9900
N4—C10	1.360 (2)	C13—H13B	0.9900
N5—C10	1.348 (2)	C14—C15	1.390 (2)
N5—H1N5	0.90 (2)	C14—C19	1.399 (2)
N5—H2N5	0.87 (2)	C15—C16	1.390 (3)
C1—C2	1.392 (2)	C15—H15A	0.9500
C1—C6	1.392 (2)	C16—C17	1.388 (3)
C1—H1A	0.9500	C16—H16A	0.9500
C2—C3	1.390 (3)	C17—C18	1.386 (3)
C2—H2A	0.9500	C17—H17A	0.9500
C3—C4	1.389 (3)	C18—C19	1.385 (3)
C3—H3A	0.9500	C18—H18A	0.9500
C4—C5	1.388 (3)	C19—H19A	0.9500
C4—H4A	0.9500

C11—S1—C13	100.87 (8)	N3—C9—N1	127.88 (15)
C9—N1—C8	105.78 (14)	N3—C9—C12	126.53 (15)
C9—N1—C7	127.68 (14)	N1—C9—C12	105.59 (14)
C8—N1—C7	125.79 (14)	N5—C10—N3	118.33 (15)
C8—N2—C12	103.57 (14)	N5—C10—N4	114.32 (15)
C9—N3—C10	111.85 (14)	N3—C10—N4	127.34 (15)
C11—N4—C10	117.98 (14)	N4—C11—C12	120.50 (15)
C10—N5—H1N5	123.6 (14)	N4—C11—S1	118.92 (13)
C10—N5—H2N5	118.7 (14)	C12—C11—S1	120.58 (13)
H1N5—N5—H2N5	117.1 (19)	C11—C12—N2	133.42 (15)
C2—C1—C6	120.00 (16)	C11—C12—C9	115.76 (15)
C2—C1—H1A	120.0	N2—C12—C9	110.81 (15)
C6—C1—H1A	120.0	C14—C13—S1	117.49 (13)
C3—C2—C1	120.58 (17)	C14—C13—H13A	107.9
C3—C2—H2A	119.7	S1—C13—H13A	107.9
C1—C2—H2A	119.7	C14—C13—H13B	107.9
C4—C3—C2	119.68 (18)	S1—C13—H13B	107.9
C4—C3—H3A	120.2	H13A—C13—H13B	107.2
C2—C3—H3A	120.2	C15—C14—C19	118.40 (17)
C5—C4—C3	119.92 (17)	C15—C14—C13	124.32 (16)
C5—C4—H4A	120.0	C19—C14—C13	117.28 (16)
C3—C4—H4A	120.0	C16—C15—C14	120.45 (17)
C4—C5—C6	120.63 (17)	C16—C15—H15A	119.8
C4—C5—H5A	119.7	C14—C15—H15A	119.8
C6—C5—H5A	119.7	C17—C16—C15	120.97 (17)
C1—C6—C5	119.13 (16)	C17—C16—H16A	119.5
C1—C6—C7	122.79 (15)	C15—C16—H16A	119.5
C5—C6—C7	118.07 (15)	C18—C17—C16	118.67 (17)
N1—C7—C6	115.28 (14)	C18—C17—H17A	120.7
N1—C7—H7A	108.5	C16—C17—H17A	120.7
C6—C7—H7A	108.5	C19—C18—C17	120.73 (18)
N1—C7—H7B	108.5	C19—C18—H18A	119.6
C6—C7—H7B	108.5	C17—C18—H18A	119.6
H7A—C7—H7B	107.5	C18—C19—C14	120.75 (17)
N2—C8—N1	114.24 (15)	C18—C19—H19A	119.6
N2—C8—H8A	122.9	C14—C19—H19A	119.6
N1—C8—H8A	122.9

C6—C1—C2—C3	−0.2 (3)	C10—N4—C11—C12	2.0 (2)
C1—C2—C3—C4	2.1 (3)	C10—N4—C11—S1	−178.00 (12)
C2—C3—C4—C5	−1.6 (3)	C13—S1—C11—N4	9.65 (15)
C3—C4—C5—C6	−0.6 (3)	C13—S1—C11—C12	−170.34 (14)
C2—C1—C6—C5	−2.0 (2)	N4—C11—C12—N2	178.87 (17)
C2—C1—C6—C7	176.53 (16)	S1—C11—C12—N2	−1.1 (3)
C4—C5—C6—C1	2.4 (2)	N4—C11—C12—C9	−1.9 (2)
C4—C5—C6—C7	−176.18 (16)	S1—C11—C12—C9	178.12 (12)
C9—N1—C7—C6	−69.9 (2)	C8—N2—C12—C11	179.67 (19)
C8—N1—C7—C6	121.46 (18)	C8—N2—C12—C9	0.37 (18)
C1—C6—C7—N1	−14.7 (2)	N3—C9—C12—C11	0.5 (3)
C5—C6—C7—N1	163.78 (15)	N1—C9—C12—C11	−179.30 (14)
C12—N2—C8—N1	−0.76 (19)	N3—C9—C12—N2	179.94 (15)
C9—N1—C8—N2	0.87 (19)	N1—C9—C12—N2	0.13 (18)
C7—N1—C8—N2	171.58 (15)	C11—S1—C13—C14	−83.26 (14)
C10—N3—C9—N1	−179.61 (16)	S1—C13—C14—C15	15.4 (2)
C10—N3—C9—C12	0.6 (2)	S1—C13—C14—C19	−165.09 (13)
C8—N1—C9—N3	179.63 (17)	C19—C14—C15—C16	1.2 (3)
C7—N1—C9—N3	9.2 (3)	C13—C14—C15—C16	−179.25 (16)
C8—N1—C9—C12	−0.55 (17)	C14—C15—C16—C17	−0.6 (3)
C7—N1—C9—C12	−171.03 (16)	C15—C16—C17—C18	−0.3 (3)
C9—N3—C10—N5	178.94 (15)	C16—C17—C18—C19	0.6 (3)
C9—N3—C10—N4	−0.5 (2)	C17—C18—C19—C14	0.0 (3)
C11—N4—C10—N5	179.75 (15)	C15—C14—C19—C18	−0.9 (3)
C11—N4—C10—N3	−0.8 (3)	C13—C14—C19—C18	179.50 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H1N5···N3ⁱ	0.91 (3)	2.14 (3)	3.040 (3)	173 (2)
C7—H7B···N3ⁱⁱ	0.99	2.57	3.548 (2)	172
C8—H8A···N2ⁱⁱⁱ	0.95	2.39	3.274 (2)	155

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H1N5···N3ⁱ	0.91 (3)	2.14 (3)	3.040 (3)	173 (2)
C7—H7B···N3ⁱⁱ	0.99	2.57	3.548 (2)	172
C8—H8A···N2ⁱⁱⁱ	0.95	2.39	3.274 (2)	155

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

Footnotes

‡Additional correspondence author, e-mail: habibahw@usm.my.

§Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

MH and HAW acknowledge the Malaysian Ministry of Science, Technology and Innovations (MOSTI) for funding the synthetic chemistry work under 304/PFARMASI/650600/I121. MH thanks Universiti Sains Malaysia for the award of a postgraduate fellowship

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