Crystal structure of 2-(adamantan-1-yl)-5-(4-bromo­phen­yl)-1,3,4-oxa­diazole

Alzoman, N.Z.; El-Emam, A.A.; Ghabbour, H.A.; Chidan Kumar, C.S.; Fun, H.-K.

doi:10.1107/S1600536814023861

organic compounds

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ISSN: 2056-9890

Volume 70| Part 12| December 2014| Pages o1231-o1232

doi:10.1107/S1600536814023861

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Crystal structure of 2-(adamantan-1-yl)-5-(4-bromophenyl)-1,3,4-oxadiazole

Nourah Z. Alzoman,^a Ali A. El-Emam,^a,^b ^* Hazem A. Ghabbour,^a C. S. Chidan Kumar ^c,^d ‡ and Hoong-Kun Fun ^a,^c ^*§

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riaydh 11451, Saudi Arabia, ^bKing Abdullah Institute for Nanotechnology (KAIN), King Saud University, Riyadh 11451, Saudi Arabia, ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^dDepartment of Chemistry, Alva's Institute of Engineering & Technology, Mijar, Moodbidri 574225, Karnataka, India
^*Correspondence e-mail: elemam5@hotmail.com, hfun.c@ksu.edu.sa

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 23 October 2014; accepted 29 October 2014; online 5 November 2014)

In the title molecule, C₁₈H₁₉BrN₂O, the benzene ring is inclined to the oxadiazole ring by 10.44 (8)°. In the crystal, C—H⋯π interactions link the molecules in a head-to-tail fashion, forming chains extending along the c-axis direction. The chains are further connected by π–π stacking interactions, with centroid–centroid distances of 3.6385 (7) Å, forming layers parallel to the bc plane.

Keywords: crystal structure; adamntane derivative; 1,3,4-oxadiazole; C—H⋯π hydrogen bonds; π–π interactions.

CCDC reference: 1031604

1. Related literature

For the biological activity of adamantane derivatives, see: Al-Abdullah et al. (2014 ); Vernier et al. (1969 ); El-Emam et al. (2013 ); Kadi et al. (2010 ); Balzarini et al. (2009 ). For the biological activity of adamantyl-1,3,4- oxadiazole derivatives, see: Al-Deeb et al. (2006 ); El-Emam et al. (2004 ); Kadi et al. (2007 ). For related adamantyl 1,3,4-oxadiazole structures, see: El-Emam et al. (2012 ); Al-Omary et al. (2014 ). For related 2,5-disubstituted 1,3,4-oxadiazole structures, see: Cordes et al. (2011 ); Franco et al. (2003 ). For the synthesis of the title compound, see: Kadi et al. (2007).

2. Experimental

2.1. Crystal data

C₁₈H₁₉BrN₂O
M_r = 359.26
Monoclinic, P 2₁ /c
a = 13.2571 (5) Å
b = 6.4753 (3) Å
c = 19.6761 (7) Å
β = 114.924 (2)°
V = 1531.76 (11) Å³
Z = 4
Mo Kα radiation
μ = 2.69 mm⁻¹
T = 293 K
0.28 × 0.22 × 0.10 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.520, T_max = 0.779
39946 measured reflections
4678 independent reflections
3996 reflections with I > 2σ(I)
R_int = 0.033

2.3. Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.069
S = 1.06
4678 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18B⋯Cg1ⁱ	0.97	2.74	3.6709 (19)	162
Symmetry code: (i) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1031604

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814023861/rz5137sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814023861/rz5137Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814023861/rz5137Isup3.cml

checkCIF report

Comment top

Adamantane derivatives have long been known for their diverse biological activities including antiviral activity against the influenza (Vernier et al., 1969) and HIV viruses (El-Emam et al., 2004; Balzarini et al., 2009). In addition, Adamantyl 1,3,4-oxadiazole derivative were reported to exhibit marked antibacterial and anti-inflammatory activities (Kadi et al., 2007, 2010). In continuation to our interest in the chemical and structural properties of adamantane derivatives (El-Emam et al., 2012; Al-Omary et al., 2014) the title compound (I) was prepared as potential bioactive agent.

In the title compound (Fig. 1), the benzene (C1–C6) ring is inclined relative to the oxadiazole (O1/N1/N2/C7/C8) ring by a dihedral angle of 10.44 (8)%. Bond lengths (Allen et al., 1987) and angles in the title compound are within normal ranges and are comparable with those reported earlier for the structure of related compounds (Cordes et al., 2011; Franco et al., 2003). In the crystal structure, the molecules are connected into head-to-tail fashion to form chains extending along the c axis via C–H···π interactions (Table 1, Fig. 2) involving the centroid of the C1–C6 benzene ring (Cg1). In addition, π–π interactions (Cg1··· Cg1ⁱ = 3.6385 (7) Å; symmetry code: (i) -x, -y, 1-z) link the chains into layers parallel to the bc plane.

Related literature top

For the biological activity of adamantane derivatives, see: Al-Abdullah et al. (2014); Vernier et al. (1969); El-Emam et al. (2013); Kadi et al. (2010); Balzarini et al. (2009). For the biological activity of adamantyl-1,3,4- oxadiazole derivatives, see: Al-Deeb et al. (2006); El-Emam et al. (2004); Kadi et al. (2007). For related adamantyl 1,3,4-oxadiazole structures, see: El-Emam et al. (2012); Al-Omary et al. (2014). For related 2,5-disubstituted 1,3,4-oxadiazole structures, see: Cordes et al. (2011); Franco et al. (2003). For the synthesis of the title compound, see: Kadi et al. (2007).

Experimental top

The title compound was prepared following our previously described method (Kadi et al., 2007). A mixture of the 4-bromobenzoic acid hydrazide (2.15 g, 0.01 mol), 1-adamantane carboxylic acid (1.8 g, 0.01 mol) and phosphorus oxychloride (8 ml) was heated under reflux for 1 h. On cooling, crushed ice (50 g) was added cautiously and the mixture was stirred for 30 min. The separated crude product was filtered, washed with water, then with a saturated sodium hydrogen carbonate solution and finally with water, dried and crystallized from EtOH/CHCl₃ (1:1 v/v) to yield 3.16 g (88%) of the title compound (C₁₈H₁₉BrN₂O) as colorless crystals. M. p.: 188–190 °C.

¹H NMR (CDCl₃): δ 1.81 (s, 6H, Adamantane-H), 2.15 (s, 9H, Adamantane-H), 7.64 (d, 2H, Ar—H, J = 8.1 Hz), 7.92 (d, 2H, Ar—H, J = 8.1 Hz). 13 C NMR: δ 27.74, 34.45, 36.29, 39.96 (Adamantane-C), 123.26, 125.99, 128.23, 132.28 (Ar—C), 163.56 (Oxadiazole C-5), 172.85 (Oxadiazole C-2).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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 50% probability displacement ellipsoids.

Fig. 2. Crystal packing of the title compound, showing the C–H···π interactions as dashed lines. Other H-atoms are omitted for clarity.

2-(Adamantan-1-yl)-5-(4-bromophenyl)-1,3,4-oxadiazole top

Crystal data top

C₁₈H₁₉BrN₂O	F(000) = 736
M_r = 359.26	D_x = 1.558 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9861 reflections
a = 13.2571 (5) Å	θ = 2.3–30.5°
b = 6.4753 (3) Å	µ = 2.69 mm⁻¹
c = 19.6761 (7) Å	T = 293 K
β = 114.924 (2)°	Block, colourless
V = 1531.76 (11) Å³	0.28 × 0.22 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4678 independent reflections
Radiation source: fine-focus sealed tube	3996 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 30.6°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
T_min = 0.520, T_max = 0.779	k = −9→9
39946 measured reflections	l = −28→28

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0261P)² + 1.1502P] where P = (F_o² + 2F_c²)/3
4678 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₁₈H₁₉BrN₂O	V = 1531.76 (11) Å³
M_r = 359.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.2571 (5) Å	µ = 2.69 mm⁻¹
b = 6.4753 (3) Å	T = 293 K
c = 19.6761 (7) Å	0.28 × 0.22 × 0.10 mm
β = 114.924 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4678 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3996 reflections with I > 2σ(I)
T_min = 0.520, T_max = 0.779	R_int = 0.033
39946 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 1.06	Δρ_max = 0.40 e Å⁻³
4678 reflections	Δρ_min = −0.50 e Å⁻³
199 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
Br1	0.032308 (13)	−0.26186 (3)	0.704343 (9)	0.02674 (6)
O1	0.23225 (9)	0.17552 (15)	0.46715 (6)	0.0156 (2)
N1	0.16178 (12)	0.4626 (2)	0.48948 (8)	0.0232 (3)
N2	0.21377 (12)	0.5092 (2)	0.44146 (8)	0.0220 (3)
C1	0.06684 (12)	0.2219 (2)	0.57759 (8)	0.0182 (3)
H1A	0.0403	0.3560	0.5652	0.022*
C2	0.03445 (12)	0.1033 (3)	0.62379 (8)	0.0204 (3)
H2A	−0.0139	0.1568	0.6425	0.025*
C3	0.07532 (12)	−0.0960 (2)	0.64159 (8)	0.0184 (3)
C4	0.14611 (13)	−0.1809 (2)	0.61362 (8)	0.0190 (3)
H4A	0.1722	−0.3153	0.6260	0.023*
C5	0.17744 (12)	−0.0626 (2)	0.56699 (8)	0.0184 (3)
H5A	0.2240	−0.1184	0.5472	0.022*
C6	0.13929 (12)	0.1400 (2)	0.54964 (8)	0.0150 (3)
C7	0.17477 (12)	0.2668 (2)	0.50242 (8)	0.0155 (3)
C8	0.25323 (12)	0.3371 (2)	0.43018 (8)	0.0149 (3)
C9	0.32131 (11)	0.2945 (2)	0.38782 (7)	0.0129 (2)
C10	0.43936 (12)	0.2361 (2)	0.44483 (8)	0.0163 (3)
H10A	0.4702	0.3473	0.4807	0.020*
H10B	0.4361	0.1132	0.4720	0.020*
C11	0.51455 (12)	0.1961 (2)	0.40472 (9)	0.0192 (3)
H11A	0.5896	0.1613	0.4417	0.023*
C12	0.51921 (13)	0.3889 (2)	0.36103 (9)	0.0220 (3)
H12A	0.5668	0.3634	0.3356	0.026*
H12B	0.5501	0.5036	0.3953	0.026*
C13	0.40153 (13)	0.4430 (2)	0.30350 (9)	0.0202 (3)
H13A	0.4046	0.5659	0.2753	0.024*
C14	0.32711 (13)	0.4874 (2)	0.34404 (8)	0.0182 (3)
H14A	0.2530	0.5245	0.3078	0.022*
H14B	0.3572	0.6025	0.3783	0.022*
C15	0.27356 (12)	0.1114 (2)	0.33328 (8)	0.0181 (3)
H15A	0.2698	−0.0105	0.3608	0.022*
H15B	0.1989	0.1439	0.2968	0.022*
C16	0.34879 (13)	0.0691 (2)	0.29311 (9)	0.0210 (3)
H16A	0.3185	−0.0468	0.2583	0.025*
C17	0.46678 (13)	0.0156 (2)	0.35028 (9)	0.0217 (3)
H17A	0.4650	−0.1076	0.3778	0.026*
H17B	0.5137	−0.0117	0.3245	0.026*
C18	0.35327 (14)	0.2619 (3)	0.24913 (9)	0.0240 (3)
H18A	0.3994	0.2350	0.2228	0.029*
H18B	0.2790	0.2962	0.2124	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02327 (9)	0.03737 (10)	0.02322 (8)	−0.00111 (7)	0.01336 (6)	0.00809 (7)
O1	0.0214 (5)	0.0128 (4)	0.0179 (5)	0.0028 (4)	0.0133 (4)	0.0014 (4)
N1	0.0332 (7)	0.0170 (6)	0.0291 (7)	0.0049 (5)	0.0227 (6)	0.0016 (5)
N2	0.0305 (7)	0.0158 (6)	0.0276 (7)	0.0048 (5)	0.0201 (6)	0.0023 (5)
C1	0.0185 (6)	0.0197 (7)	0.0187 (6)	0.0043 (5)	0.0101 (5)	0.0008 (5)
C2	0.0185 (7)	0.0274 (8)	0.0183 (7)	0.0044 (6)	0.0107 (6)	−0.0005 (6)
C3	0.0167 (6)	0.0261 (7)	0.0136 (6)	−0.0029 (6)	0.0076 (5)	0.0011 (5)
C4	0.0206 (7)	0.0174 (6)	0.0202 (7)	0.0021 (6)	0.0096 (6)	0.0013 (5)
C5	0.0196 (7)	0.0186 (7)	0.0205 (7)	0.0028 (5)	0.0118 (6)	−0.0005 (5)
C6	0.0157 (6)	0.0166 (6)	0.0135 (6)	0.0013 (5)	0.0068 (5)	−0.0013 (5)
C7	0.0164 (6)	0.0160 (6)	0.0163 (6)	0.0025 (5)	0.0089 (5)	−0.0018 (5)
C8	0.0168 (6)	0.0129 (6)	0.0150 (6)	0.0003 (5)	0.0067 (5)	0.0010 (5)
C9	0.0147 (6)	0.0108 (6)	0.0139 (6)	0.0006 (5)	0.0068 (5)	0.0005 (4)
C10	0.0164 (6)	0.0165 (6)	0.0152 (6)	0.0014 (5)	0.0060 (5)	0.0021 (5)
C11	0.0147 (6)	0.0208 (7)	0.0223 (7)	0.0026 (5)	0.0081 (6)	0.0046 (6)
C12	0.0221 (7)	0.0193 (7)	0.0296 (8)	−0.0039 (6)	0.0158 (6)	0.0005 (6)
C13	0.0269 (8)	0.0165 (6)	0.0226 (7)	0.0027 (6)	0.0156 (6)	0.0064 (5)
C14	0.0224 (7)	0.0137 (6)	0.0212 (7)	0.0042 (5)	0.0117 (6)	0.0050 (5)
C15	0.0176 (7)	0.0185 (7)	0.0193 (7)	−0.0047 (5)	0.0089 (6)	−0.0057 (5)
C16	0.0270 (8)	0.0188 (7)	0.0224 (7)	−0.0040 (6)	0.0153 (6)	−0.0074 (6)
C17	0.0279 (8)	0.0150 (6)	0.0314 (8)	0.0052 (6)	0.0214 (7)	0.0029 (6)
C18	0.0278 (8)	0.0306 (8)	0.0173 (7)	0.0027 (7)	0.0130 (6)	0.0013 (6)

Geometric parameters (Å, º) top

Br1—C3	1.8965 (14)	C10—H10B	0.9700
O1—C7	1.3629 (16)	C11—C17	1.530 (2)
O1—C8	1.3682 (17)	C11—C12	1.532 (2)
N1—C7	1.2902 (19)	C11—H11A	0.9800
N1—N2	1.4169 (18)	C12—C13	1.533 (2)
N2—C8	1.2891 (18)	C12—H12A	0.9700
C1—C2	1.389 (2)	C12—H12B	0.9700
C1—C6	1.3968 (19)	C13—C18	1.534 (2)
C1—H1A	0.9300	C13—C14	1.535 (2)
C2—C3	1.386 (2)	C13—H13A	0.9800
C2—H2A	0.9300	C14—H14A	0.9700
C3—C4	1.386 (2)	C14—H14B	0.9700
C4—C5	1.386 (2)	C15—C16	1.536 (2)
C4—H4A	0.9300	C15—H15A	0.9700
C5—C6	1.396 (2)	C15—H15B	0.9700
C5—H5A	0.9300	C16—C17	1.533 (2)
C6—C7	1.4584 (19)	C16—C18	1.534 (2)
C8—C9	1.4899 (19)	C16—H16A	0.9800
C9—C14	1.5376 (19)	C17—H17A	0.9700
C9—C10	1.5397 (19)	C17—H17B	0.9700
C9—C15	1.5447 (19)	C18—H18A	0.9700
C10—C11	1.532 (2)	C18—H18B	0.9700
C10—H10A	0.9700

C7—O1—C8	102.80 (11)	C12—C11—H11A	109.6
C7—N1—N2	106.19 (12)	C11—C12—C13	109.36 (12)
C8—N2—N1	106.11 (12)	C11—C12—H12A	109.8
C2—C1—C6	120.09 (14)	C13—C12—H12A	109.8
C2—C1—H1A	120.0	C11—C12—H12B	109.8
C6—C1—H1A	120.0	C13—C12—H12B	109.8
C3—C2—C1	118.96 (13)	H12A—C12—H12B	108.3
C3—C2—H2A	120.5	C12—C13—C18	109.63 (13)
C1—C2—H2A	120.5	C12—C13—C14	109.63 (12)
C4—C3—C2	121.79 (14)	C18—C13—C14	109.58 (13)
C4—C3—Br1	118.26 (12)	C12—C13—H13A	109.3
C2—C3—Br1	119.93 (11)	C18—C13—H13A	109.3
C3—C4—C5	119.04 (14)	C14—C13—H13A	109.3
C3—C4—H4A	120.5	C13—C14—C9	109.50 (11)
C5—C4—H4A	120.5	C13—C14—H14A	109.8
C4—C5—C6	120.16 (13)	C9—C14—H14A	109.8
C4—C5—H5A	119.9	C13—C14—H14B	109.8
C6—C5—H5A	119.9	C9—C14—H14B	109.8
C5—C6—C1	119.93 (13)	H14A—C14—H14B	108.2
C5—C6—C7	120.28 (13)	C16—C15—C9	109.24 (12)
C1—C6—C7	119.80 (13)	C16—C15—H15A	109.8
N1—C7—O1	112.48 (13)	C9—C15—H15A	109.8
N1—C7—C6	128.83 (13)	C16—C15—H15B	109.8
O1—C7—C6	118.67 (12)	C9—C15—H15B	109.8
N2—C8—O1	112.42 (12)	H15A—C15—H15B	108.3
N2—C8—C9	129.92 (13)	C17—C16—C18	109.12 (13)
O1—C8—C9	117.56 (12)	C17—C16—C15	110.23 (12)
C8—C9—C14	110.37 (11)	C18—C16—C15	109.44 (13)
C8—C9—C10	107.90 (11)	C17—C16—H16A	109.3
C14—C9—C10	109.40 (11)	C18—C16—H16A	109.3
C8—C9—C15	111.30 (11)	C15—C16—H16A	109.3
C14—C9—C15	109.70 (12)	C11—C17—C16	109.56 (12)
C10—C9—C15	108.11 (11)	C11—C17—H17A	109.8
C11—C10—C9	110.40 (11)	C16—C17—H17A	109.8
C11—C10—H10A	109.6	C11—C17—H17B	109.8
C9—C10—H10A	109.6	C16—C17—H17B	109.8
C11—C10—H10B	109.6	H17A—C17—H17B	108.2
C9—C10—H10B	109.6	C13—C18—C16	109.45 (12)
H10A—C10—H10B	108.1	C13—C18—H18A	109.8
C17—C11—C10	108.83 (12)	C16—C18—H18A	109.8
C17—C11—C12	109.40 (13)	C13—C18—H18B	109.8
C10—C11—C12	109.87 (12)	C16—C18—H18B	109.8
C17—C11—H11A	109.6	H18A—C18—H18B	108.2
C10—C11—H11A	109.6

C7—N1—N2—C8	−0.10 (18)	O1—C8—C9—C15	52.62 (16)
C6—C1—C2—C3	0.1 (2)	C8—C9—C10—C11	−178.46 (11)
C1—C2—C3—C4	−1.0 (2)	C14—C9—C10—C11	−58.36 (15)
C1—C2—C3—Br1	−179.84 (11)	C15—C9—C10—C11	61.06 (15)
C2—C3—C4—C5	0.4 (2)	C9—C10—C11—C17	−61.10 (15)
Br1—C3—C4—C5	179.30 (11)	C9—C10—C11—C12	58.67 (16)
C3—C4—C5—C6	1.0 (2)	C17—C11—C12—C13	60.01 (16)
C4—C5—C6—C1	−1.8 (2)	C10—C11—C12—C13	−59.40 (16)
C4—C5—C6—C7	178.16 (14)	C11—C12—C13—C18	−59.80 (16)
C2—C1—C6—C5	1.3 (2)	C11—C12—C13—C14	60.53 (16)
C2—C1—C6—C7	−178.74 (14)	C12—C13—C14—C9	−60.59 (16)
N2—N1—C7—O1	0.28 (18)	C18—C13—C14—C9	59.77 (16)
N2—N1—C7—C6	178.56 (14)	C8—C9—C14—C13	177.65 (12)
C8—O1—C7—N1	−0.34 (16)	C10—C9—C14—C13	59.08 (15)
C8—O1—C7—C6	−178.81 (12)	C15—C9—C14—C13	−59.35 (15)
C5—C6—C7—N1	−168.91 (16)	C8—C9—C15—C16	−178.05 (12)
C1—C6—C7—N1	11.1 (2)	C14—C9—C15—C16	59.51 (15)
C5—C6—C7—O1	9.3 (2)	C10—C9—C15—C16	−59.72 (15)
C1—C6—C7—O1	−170.73 (13)	C9—C15—C16—C17	59.96 (16)
N1—N2—C8—O1	−0.12 (17)	C9—C15—C16—C18	−60.05 (16)
N1—N2—C8—C9	−176.25 (14)	C10—C11—C17—C16	59.51 (15)
C7—O1—C8—N2	0.27 (16)	C12—C11—C17—C16	−60.55 (15)
C7—O1—C8—C9	176.93 (12)	C18—C16—C17—C11	60.45 (15)
N2—C8—C9—C14	−9.4 (2)	C15—C16—C17—C11	−59.76 (16)
O1—C8—C9—C14	174.68 (12)	C12—C13—C18—C16	59.93 (16)
N2—C8—C9—C10	110.13 (17)	C14—C13—C18—C16	−60.43 (16)
O1—C8—C9—C10	−65.84 (15)	C17—C16—C18—C13	−60.03 (16)
N2—C8—C9—C15	−131.41 (16)	C15—C16—C18—C13	60.66 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···Cg1ⁱ	0.97	2.74	3.6709 (19)	162

Symmetry code: (i) x, −y−1/2, z−3/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···Cg1ⁱ	0.9700	2.74	3.6709 (19)	162.00

Symmetry code: (i) x, −y−1/2, z−3/2.

Footnotes

‡Thomson Reuters ResearcherID: C-3194-2011.

§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 (USM) for a postdoctoral research fellowship.

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Volume 70| Part 12| December 2014| Pages o1231-o1232

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