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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Apr 13;68(Pt 5):o1356. doi: 10.1107/S160053681201464X

2-{[5-(Adamantan-1-yl)-4-methyl-4H-1,2,4-triazol-3-yl]sulfan­yl}-N,N-dimethyl­ethanamine

Ali A El-Emam a, Siham Lahsasni b, Hanadi H Asiri a, Ching Kheng Quah c,‡, Hoong-Kun Fun c,*,§
PMCID: PMC3344488  PMID: 22590250

Abstract

In the title compound, C17H28N4S, the 1,2,4-triazole ring is nearly planar [maximum deviation = 0.005 (2) Å]. There are no significant hydrogen bonds observed in the crystal structure. The crystal studied was a non-merohedral twin, the refined ratio of twin components being 0.281 (3):0.719 (3).

Related literature  

For the biological activity of adamantyl derivatives see: Al-Omar et al. (2010 ▶); Al-Deeb et al. (2006 ▶); El-Emam et al. (2004 ▶); Kadi et al. (2007 ▶, 2010 ▶); Vernier et al. (1969 ▶). For the structures of related adamantyl-1,2,4-triazoles, see: Almutairi et al. (2012 ▶); Al-Tamimi et al. (2010 ▶); Al-Abdullah et al. (2012 ▶). For the structures of substituted sulfanyl-1,2,4-triazoles, see: Fun et al. (2011 ▶); Wang et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).graphic file with name e-68-o1356-scheme1.jpg

Experimental  

Crystal data  

  • C17H28N4S

  • M r = 320.49

  • Monoclinic, Inline graphic

  • a = 12.5133 (7) Å

  • b = 10.3779 (5) Å

  • c = 14.3044 (8) Å

  • β = 106.766 (3)°

  • V = 1778.63 (16) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 1.62 mm−1

  • T = 296 K

  • 0.64 × 0.59 × 0.05 mm

Data collection  

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.204, T max = 0.923

  • 3267 measured reflections

  • 3267 independent reflections

  • 2846 reflections with I > 2σ(I)

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.064

  • wR(F 2) = 0.184

  • S = 1.13

  • 3267 reflections

  • 203 parameters

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.37 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 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201464X/rz2734sup1.cif

e-68-o1356-sup1.cif (27.4KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201464X/rz2734Isup2.hkl

e-68-o1356-Isup2.hkl (160.3KB, hkl)

Supplementary material file. DOI: 10.1107/S160053681201464X/rz2734Isup3.cml

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

Acknowledgments

The financial support of the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, is greatly appreciated. HKF and CKQ thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160).

supplementary crystallographic information

Comment

Considerable attention has been devoted to adamantane derivatives which have long been known for their diverse biological properties as antiviral against the influenza (Vernier et al., 1969) and HIV viruses (El-Emam, Al-Deeb, Al-Omar & Lehmann, 2004). Moreover, adamantane derivatives were recently reported to exhibit marked antibacterial activity (Kadi et al., 2007, 2010). In continuation of our interest in the chemical and pharmacological properties of adamantane derivatives, we synthesized the title compound as a potential chemotherapeutic agent.

In the title molecule, Fig. 1, the 1,2,4-triazole ring (N1-N3/C11/C12) is nearly planar with a maximum deviation of 0.005 (2) Å at atom N2. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those reported for related structures (Almutairi et al., 2012; Al-Tamimi et al., 2010; Al-Abdullah et al., 2012; Fun et al., 2011; Wang et al., 2011). The crystal studied was a non-merohedral twin, the refined ratio of twin components being 0.281 (3):0.719 (3). There are no significant hydrogen bonds observed in this compound.

Experimental

A mixture of 3-(adamantan-1-yl)-4-methyl-4H-1,2,4-triazole-5-thiol (2.49 g, 0.01 mol), potassium hydroxide (1.12 g, 0.02 mol) and 2-dimethylaminoethyl chloride hydrochloride (1.44 g, 0.01 mol) in ethanol (15 ml) was heated under reflux with stirring for 3 h and the solvent was distilled off in vacuo. The obtained residue was washed with water and purified by column chromatography on silica gel column using CHCl3:MeOH (9:1 v/v) as eluent to yield 2.02 g (63%) of the title compound as colorless powder. M.p. 133-135°C. Single crystals suitable for X-ray diffraction were obtained by crystallization from aqueous ethanol. 1H NMR (CDCl3, 500.13 MHz): δ 1.69-1.75 (m, 6H, adamantane-H), 2.04-2.85 (m, 9H, adamantane-H), 2.21 (s, 6H, 2xCH3), 2.62 (t, 2H, CH2N, J = 6.5 Hz), 3.28 (t, 2H, SCH2, J = 6.5 Hz), 3.59 (s, 3H, CH3). 13C NMR (CDCl3, 125.76 MHz): δ 28.07, 34.98, 36.50, 49.56 (adamantane-C), 31.05 (CH3), 32.33 (SCH2), 45.21 (2xCH3), 58.24 (CH2N), 152.16, 161.21 (triazole C).

Refinement

All hydrogen atoms were positioned geometrically [C–H = 0.96–0.98 Å] and refined using a riding model, with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups. The crystal studied was a non-merohedral twin, the refined ratio of twin components being 0.281 (3):0.719 (3).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C17H28N4S F(000) = 696
Mr = 320.49 Dx = 1.197 Mg m−3
Monoclinic, P21/c Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc Cell parameters from 3932 reflections
a = 12.5133 (7) Å θ = 7.7–69.2°
b = 10.3779 (5) Å µ = 1.62 mm−1
c = 14.3044 (8) Å T = 296 K
β = 106.766 (3)° Plate, colourless
V = 1778.63 (16) Å3 0.64 × 0.59 × 0.05 mm
Z = 4
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Data collection

Bruker SMART APEXII CCD area-detector diffractometer 3267 independent reflections
Radiation source: fine-focus sealed tube 2846 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.000
φ and ω scans θmax = 69.8°, θmin = 7.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009) h = −15→14
Tmin = 0.204, Tmax = 0.923 k = −12→12
3267 measured reflections l = 0→16
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Refinement

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)] = 0.064 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184 H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.P)2 + 1.1111P] where P = (Fo2 + 2Fc2)/3
3267 reflections (Δ/σ)max = 0.001
203 parameters Δρmax = 0.32 e Å−3
0 restraints Δρmin = −0.37 e Å−3
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Special details

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

x y z Uiso*/Ueq
S1 0.59451 (7) 0.30472 (8) 0.05471 (7) 0.0589 (3)
N1 0.4306 (2) 0.2967 (2) 0.14471 (19) 0.0478 (6)
N4 0.7649 (3) 0.2967 (3) −0.0644 (2) 0.0630 (7)
C9 0.2838 (2) 0.2248 (3) 0.2293 (2) 0.0476 (7)
C10 0.3344 (3) 0.2856 (4) 0.3307 (3) 0.0672 (9)
H10A 0.3944 0.2315 0.3689 0.081*
H10B 0.3653 0.3694 0.3234 0.081*
C6 0.2449 (4) 0.3001 (5) 0.3838 (3) 0.0814 (12)
H6A 0.2779 0.3402 0.4477 0.098*
C5 0.1995 (4) 0.1692 (5) 0.3976 (3) 0.0893 (14)
H5A 0.1441 0.1778 0.4328 0.107*
H5B 0.2594 0.1149 0.4359 0.107*
C4 0.1465 (4) 0.1071 (4) 0.2985 (3) 0.0765 (11)
H4A 0.1169 0.0222 0.3077 0.092*
C3 0.0526 (3) 0.1919 (5) 0.2391 (3) 0.0817 (13)
H3A 0.0183 0.1524 0.1761 0.098*
H3B −0.0041 0.2011 0.2728 0.098*
C13 0.6508 (4) 0.1620 (4) 0.0134 (4) 0.0803 (12)
H13A 0.6560 0.0927 0.0600 0.096*
H13B 0.6015 0.1344 −0.0490 0.096*
C2 0.0985 (3) 0.3229 (4) 0.2249 (3) 0.0757 (11)
H2A 0.0375 0.3775 0.1869 0.091*
C7 0.1513 (4) 0.3853 (5) 0.3230 (4) 0.0861 (13)
H7A 0.0954 0.3977 0.3571 0.103*
H7B 0.1810 0.4691 0.3136 0.103*
C1 0.1858 (3) 0.3084 (4) 0.1699 (3) 0.0653 (9)
H1A 0.2132 0.3927 0.1586 0.078*
H1B 0.1520 0.2684 0.1069 0.078*
C8 0.2350 (3) 0.0923 (3) 0.2444 (3) 0.0666 (9)
H8A 0.2018 0.0521 0.1814 0.080*
H8B 0.2944 0.0367 0.2817 0.080*
C11 0.3702 (2) 0.2040 (3) 0.1772 (2) 0.0477 (7)
N2 0.4021 (2) 0.0897 (2) 0.1572 (2) 0.0577 (7)
N3 0.4859 (3) 0.1046 (3) 0.1120 (2) 0.0599 (7)
C12 0.5001 (3) 0.2289 (3) 0.1054 (2) 0.0516 (7)
C14 0.7641 (4) 0.1909 (5) 0.0031 (4) 0.0874 (14)
H14A 0.8139 0.2124 0.0669 0.105*
H14B 0.7930 0.1140 −0.0196 0.105*
C16 0.7117 (7) 0.2636 (6) −0.1633 (5) 0.126 (2)
H16A 0.7180 0.3341 −0.2048 0.189*
H16B 0.6342 0.2457 −0.1713 0.189*
H16C 0.7468 0.1886 −0.1805 0.189*
C17 0.4269 (3) 0.4366 (3) 0.1495 (3) 0.0633 (9)
H17A 0.4899 0.4723 0.1330 0.095*
H17B 0.4292 0.4626 0.2145 0.095*
H17C 0.3593 0.4674 0.1043 0.095*
C15 0.8793 (5) 0.3349 (7) −0.0500 (6) 0.120 (2)
H15A 0.8822 0.4023 −0.0951 0.181*
H15B 0.9217 0.2623 −0.0608 0.181*
H15C 0.9101 0.3655 0.0156 0.181*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
S1 0.0605 (5) 0.0553 (5) 0.0668 (6) −0.0051 (3) 0.0278 (4) −0.0023 (4)
N1 0.0524 (14) 0.0418 (13) 0.0497 (15) 0.0000 (10) 0.0156 (11) 0.0003 (10)
N4 0.0598 (17) 0.0665 (18) 0.0661 (19) 0.0050 (13) 0.0236 (14) 0.0030 (14)
C9 0.0478 (15) 0.0505 (16) 0.0430 (16) 0.0012 (12) 0.0105 (13) −0.0010 (12)
C10 0.060 (2) 0.084 (2) 0.051 (2) −0.0009 (18) 0.0042 (16) −0.0097 (17)
C6 0.076 (3) 0.113 (4) 0.054 (2) −0.003 (2) 0.0162 (19) −0.021 (2)
C5 0.082 (3) 0.133 (4) 0.059 (3) 0.012 (3) 0.031 (2) 0.017 (2)
C4 0.079 (3) 0.078 (3) 0.083 (3) −0.011 (2) 0.039 (2) 0.003 (2)
C3 0.056 (2) 0.123 (4) 0.070 (3) −0.011 (2) 0.0232 (19) −0.009 (2)
C13 0.081 (3) 0.064 (2) 0.114 (4) 0.0078 (19) 0.056 (3) 0.006 (2)
C2 0.057 (2) 0.095 (3) 0.073 (3) 0.0195 (19) 0.0154 (18) 0.007 (2)
C7 0.085 (3) 0.092 (3) 0.091 (3) 0.009 (2) 0.042 (3) −0.018 (2)
C1 0.059 (2) 0.080 (2) 0.055 (2) 0.0125 (16) 0.0139 (16) 0.0096 (17)
C8 0.070 (2) 0.063 (2) 0.072 (2) −0.0051 (16) 0.0289 (18) 0.0026 (17)
C11 0.0505 (16) 0.0440 (15) 0.0476 (17) 0.0002 (12) 0.0126 (13) 0.0023 (12)
N2 0.0657 (16) 0.0454 (14) 0.0686 (18) 0.0029 (12) 0.0299 (14) 0.0032 (12)
N3 0.0682 (17) 0.0466 (15) 0.0727 (19) 0.0041 (12) 0.0327 (15) 0.0027 (12)
C12 0.0531 (17) 0.0499 (17) 0.0499 (18) 0.0020 (13) 0.0118 (14) 0.0008 (13)
C14 0.080 (3) 0.094 (3) 0.096 (3) 0.024 (2) 0.038 (3) 0.024 (3)
C16 0.181 (6) 0.097 (4) 0.082 (4) 0.030 (4) 0.008 (4) −0.013 (3)
C17 0.069 (2) 0.0442 (17) 0.080 (2) −0.0017 (15) 0.0273 (18) −0.0028 (15)
C15 0.082 (3) 0.137 (5) 0.151 (6) 0.003 (3) 0.047 (4) 0.032 (4)
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Geometric parameters (Å, º)

S1—C12 1.742 (3) C13—C14 1.498 (6)
S1—C13 1.811 (4) C13—H13A 0.9700
N1—C12 1.361 (4) C13—H13B 0.9700
N1—C11 1.384 (4) C2—C7 1.513 (7)
N1—C17 1.455 (4) C2—C1 1.527 (5)
N4—C16 1.421 (7) C2—H2A 0.9800
N4—C15 1.441 (6) C7—H7A 0.9700
N4—C14 1.464 (5) C7—H7B 0.9700
C9—C11 1.495 (4) C1—H1A 0.9700
C9—C10 1.539 (5) C1—H1B 0.9700
C9—C1 1.542 (4) C8—H8A 0.9700
C9—C8 1.546 (5) C8—H8B 0.9700
C10—C6 1.531 (6) C11—N2 1.310 (4)
C10—H10A 0.9700 N2—N3 1.390 (4)
C10—H10B 0.9700 N3—C12 1.309 (4)
C6—C5 1.508 (7) C14—H14A 0.9700
C6—C7 1.524 (7) C14—H14B 0.9700
C6—H6A 0.9800 C16—H16A 0.9600
C5—C4 1.524 (7) C16—H16B 0.9600
C5—H5A 0.9700 C16—H16C 0.9600
C5—H5B 0.9700 C17—H17A 0.9600
C4—C3 1.517 (7) C17—H17B 0.9600
C4—C8 1.531 (5) C17—H17C 0.9600
C4—H4A 0.9800 C15—H15A 0.9600
C3—C2 1.513 (7) C15—H15B 0.9600
C3—H3A 0.9700 C15—H15C 0.9600
C3—H3B 0.9700
C12—S1—C13 98.05 (17) C7—C2—H2A 109.2
C12—N1—C11 104.8 (2) C1—C2—H2A 109.2
C12—N1—C17 124.6 (3) C2—C7—C6 109.8 (4)
C11—N1—C17 130.5 (3) C2—C7—H7A 109.7
C16—N4—C15 111.7 (5) C6—C7—H7A 109.7
C16—N4—C14 112.6 (4) C2—C7—H7B 109.7
C15—N4—C14 107.9 (4) C6—C7—H7B 109.7
C11—C9—C10 111.7 (3) H7A—C7—H7B 108.2
C11—C9—C1 112.4 (3) C2—C1—C9 110.2 (3)
C10—C9—C1 109.5 (3) C2—C1—H1A 109.6
C11—C9—C8 108.2 (3) C9—C1—H1A 109.6
C10—C9—C8 107.7 (3) C2—C1—H1B 109.6
C1—C9—C8 107.1 (3) C9—C1—H1B 109.6
C6—C10—C9 110.3 (3) H1A—C1—H1B 108.1
C6—C10—H10A 109.6 C4—C8—C9 110.7 (3)
C9—C10—H10A 109.6 C4—C8—H8A 109.5
C6—C10—H10B 109.6 C9—C8—H8A 109.5
C9—C10—H10B 109.6 C4—C8—H8B 109.5
H10A—C10—H10B 108.1 C9—C8—H8B 109.5
C5—C6—C7 109.9 (4) H8A—C8—H8B 108.1
C5—C6—C10 109.5 (4) N2—C11—N1 109.0 (3)
C7—C6—C10 109.0 (4) N2—C11—C9 123.3 (3)
C5—C6—H6A 109.5 N1—C11—C9 127.6 (3)
C7—C6—H6A 109.5 C11—N2—N3 108.6 (3)
C10—C6—H6A 109.5 C12—N3—N2 106.3 (3)
C6—C5—C4 109.8 (3) N3—C12—N1 111.2 (3)
C6—C5—H5A 109.7 N3—C12—S1 126.8 (3)
C4—C5—H5A 109.7 N1—C12—S1 122.0 (2)
C6—C5—H5B 109.7 N4—C14—C13 113.7 (4)
C4—C5—H5B 109.7 N4—C14—H14A 108.8
H5A—C5—H5B 108.2 C13—C14—H14A 108.8
C3—C4—C5 109.5 (4) N4—C14—H14B 108.8
C3—C4—C8 109.4 (4) C13—C14—H14B 108.8
C5—C4—C8 109.2 (4) H14A—C14—H14B 107.7
C3—C4—H4A 109.6 N4—C16—H16A 109.5
C5—C4—H4A 109.6 N4—C16—H16B 109.5
C8—C4—H4A 109.6 H16A—C16—H16B 109.5
C2—C3—C4 109.5 (3) N4—C16—H16C 109.5
C2—C3—H3A 109.8 H16A—C16—H16C 109.5
C4—C3—H3A 109.8 H16B—C16—H16C 109.5
C2—C3—H3B 109.8 N1—C17—H17A 109.5
C4—C3—H3B 109.8 N1—C17—H17B 109.5
H3A—C3—H3B 108.2 H17A—C17—H17B 109.5
C14—C13—S1 109.7 (3) N1—C17—H17C 109.5
C14—C13—H13A 109.7 H17A—C17—H17C 109.5
S1—C13—H13A 109.7 H17B—C17—H17C 109.5
C14—C13—H13B 109.7 N4—C15—H15A 109.5
S1—C13—H13B 109.7 N4—C15—H15B 109.5
H13A—C13—H13B 108.2 H15A—C15—H15B 109.5
C3—C2—C7 110.0 (4) N4—C15—H15C 109.5
C3—C2—C1 109.7 (4) H15A—C15—H15C 109.5
C7—C2—C1 109.6 (3) H15B—C15—H15C 109.5
C3—C2—H2A 109.2
C11—C9—C10—C6 −177.5 (3) C10—C9—C8—C4 58.6 (4)
C1—C9—C10—C6 57.3 (4) C1—C9—C8—C4 −59.2 (4)
C8—C9—C10—C6 −58.8 (4) C12—N1—C11—N2 −0.5 (4)
C9—C10—C6—C5 60.9 (4) C17—N1—C11—N2 −179.8 (3)
C9—C10—C6—C7 −59.3 (5) C12—N1—C11—C9 178.0 (3)
C7—C6—C5—C4 58.9 (5) C17—N1—C11—C9 −1.3 (5)
C10—C6—C5—C4 −60.8 (5) C10—C9—C11—N2 113.2 (4)
C6—C5—C4—C3 −59.6 (5) C1—C9—C11—N2 −123.3 (4)
C6—C5—C4—C8 60.2 (5) C8—C9—C11—N2 −5.3 (4)
C5—C4—C3—C2 59.8 (5) C10—C9—C11—N1 −65.1 (4)
C8—C4—C3—C2 −59.8 (5) C1—C9—C11—N1 58.4 (4)
C12—S1—C13—C14 −157.1 (3) C8—C9—C11—N1 176.4 (3)
C4—C3—C2—C7 −59.9 (5) N1—C11—N2—N3 0.8 (4)
C4—C3—C2—C1 60.7 (4) C9—C11—N2—N3 −177.8 (3)
C3—C2—C7—C6 59.1 (5) C11—N2—N3—C12 −0.8 (4)
C1—C2—C7—C6 −61.6 (5) N2—N3—C12—N1 0.5 (4)
C5—C6—C7—C2 −58.6 (5) N2—N3—C12—S1 −179.9 (3)
C10—C6—C7—C2 61.3 (5) C11—N1—C12—N3 −0.1 (4)
C3—C2—C1—C9 −61.4 (4) C17—N1—C12—N3 179.3 (3)
C7—C2—C1—C9 59.4 (5) C11—N1—C12—S1 −179.7 (2)
C11—C9—C1—C2 178.2 (3) C17—N1—C12—S1 −0.3 (5)
C10—C9—C1—C2 −57.1 (4) C13—S1—C12—N3 3.1 (4)
C8—C9—C1—C2 59.5 (4) C13—S1—C12—N1 −177.3 (3)
C3—C4—C8—C9 60.2 (5) C16—N4—C14—C13 −69.9 (6)
C5—C4—C8—C9 −59.7 (5) C15—N4—C14—C13 166.4 (5)
C11—C9—C8—C4 179.4 (3) S1—C13—C14—N4 −58.1 (5)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2734).

References

  1. Al-Abdullah, E. S., Asiri, H. H., El-Emam, A. & Ng, S. W. (2012). Acta Cryst. E68, o344. [DOI] [PMC free article] [PubMed]
  2. Al-Deeb, O. A., Al-Omar, M. A., El-Brollosy, N. R., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2006). Arzneim. Forsch./Drug Res. 56, 40–47. [DOI] [PubMed]
  3. Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  4. Almutairi, M. S., Al-Shehri, M. M., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o656. [DOI] [PMC free article] [PubMed]
  5. Al-Omar, M. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2010). Molecules, 15, 2526–2550. [DOI] [PMC free article] [PubMed]
  6. Al-Tamimi, A.-M. S., Bari, A., Al-Omar, M. A., Alrashood, K. A. & El-Emam, A. A. (2010). Acta Cryst. E66, o1756. [DOI] [PMC free article] [PubMed]
  7. Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  8. El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107–5113. [DOI] [PubMed]
  9. Fun, H.-K., Asik, S. I. J., Chandrakantha, B., Isloor, A. M. & Shetty, P. (2011). Acta Cryst. E67, o3422–o3423. [DOI] [PMC free article] [PubMed]
  10. Kadi, A. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2010). Eur. J. Med. Chem. 45, 5006–5011. [DOI] [PubMed]
  11. Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem 42, 235–242. [DOI] [PubMed]
  12. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  13. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
  14. Vernier, V. G., Harmon, J. B., Stump, J. M., Lynes, T. L., Marvel, M. P. & Smith, D. H. (1969). Toxicol. Appl. Pharmacol. 15, 642–665. [DOI] [PubMed]
  15. Wang, W., Liu, Q., Xu, C., Wu, W. & Gao, Y. (2011). Acta Cryst. E67, o2236. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201464X/rz2734sup1.cif

e-68-o1356-sup1.cif (27.4KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201464X/rz2734Isup2.hkl

e-68-o1356-Isup2.hkl (160.3KB, hkl)

Supplementary material file. DOI: 10.1107/S160053681201464X/rz2734Isup3.cml

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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