Crystal structure of 2-(adamantan-1-yl)-5-(4-bromo-phen-yl)-1,3,4-oxa-diazole.

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

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 ▶).

Experimental

Crystal data

C18H19BrN2O

M = 359.26

Monoclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.069

S = 1.06

4678 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.50 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814023861/rz5137sup1.cif

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

Click here for additional data file.

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

Click here for additional data file.

. DOI: 10.1107/S1600536814023861/rz5137fig1.tif

The mol­ecular structure of the title compound with 50% probability displacement ellipsoids.

Click here for additional data file.

. DOI: 10.1107/S1600536814023861/rz5137fig2.tif

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

CCDC reference: 1031604

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H19BrN2O	F(000) = 736
Mr = 359.26	Dx = 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

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

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(Fo2) + (0.0261P)2 + 1.1502P] where P = (Fo2 + 2Fc2)/3
4678 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the C1C6 ring.

DHA	DH	HA	D A	DHA
C18H18B Cg1i	0.97	2.74	3.6709(19)	162

Symmetry code: (i) .