Crystal structures and Hirshfeld surface analysis of 2-(adamantan-1-yl)-5-(4-fluoro­phen­yl)-1,3,4-oxa­diazole and 2-(adamantan-1-yl)-5-(4-chloro­phen­yl)-1,3,4-oxa­diazole

Al-Wahaibi, L.H.; Alsfouk, A.; El-Emam, A.A.; Blacque, O.

doi:10.1107/S2056989019004651

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 75| Part 5| May 2019| Pages 611-615

https://doi.org/10.1107/S2056989019004651

Open

access

Crystal structures and Hirshfeld surface analysis of 2-(adamantan-1-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole and 2-(adamantan-1-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole

Lamya H. Al-Wahaibi,^a Aisha Alsfouk,^b Ali A. El-Emam ^c and Olivier Blacque ^d ^*

^aDepartment of Chemistry, College of Sciences, Princess Nourah Bint Abdulrahman University, Riyadh 11671, Saudi Arabia, ^bDepartment of Pharmaceutical Sciences, College of Pharmacy, Princess Nourah Bint Abdulrahman University, Riyadh 11671, Saudi Arabia, ^cDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt, and ^dDepartment of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland
^*Correspondence e-mail: olivier.blacque@chem.uzh.ch

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 22 March 2019; accepted 5 April 2019; online 12 April 2019)

The crystal structures of the title adamantane-oxadiazole hybrid compounds, C₁₈H₁₉FN₂O (I) and C₁₈H₁₉ClN₂O (II), are built up from an adamantane unit and a halogenophenyl ring, [X = F (I), Cl (II)], in position 5 on the central 1,3,4-oxadiazole unit. The molecular structures are very similar, only the relative orientation of the halogenophenyl ring in comparison with the central five-membered ring differs slightly. In the crystals of both compounds, molecules are linked by pairs of C—H⋯N hydrogen bonds, forming inversion dimers with R²₂(12) ring motifs. In (I) the dimers are connected by C—H⋯F interactions, forming slabs lying parallel to the bc plane. In (II), the dimers are linked by C—H⋯π and offset π–π interactions [interplanar distance = 3.4039 (9) Å], forming layers parallel to (10 $[\overline{1}]$ ).

Keywords: crystal structure; adamantyl derivatives; 1,3,4-oxadiazoles; C—H⋯N hydrogen bonds; C—H⋯F interactions; Hirshfeld surface analysis..

CCDC references: 1908204; 1908203

1. Chemical context

Considerable attention has been devoted to adamantane derivatives, which have long been known for their diverse biological properties (Liu et al., 2011 ; Lamoureux & Artavia, 2010 ). In view of the pronounced lipophilicity of the adamantane cage, it has been observed that adamantyl-bearing compounds are characterized by high therapeutic indices (Wanka et al., 2013 ). Sixty years ago, the first adamantane-based drug, amantadine, was discovered to be an efficient therapy for the treatment of Influenza A infection (Davies et al., 1964 ; Togo et al., 1968 ). As a result of intensive research based on adamantane derivatives, the adamantane nucleus was further recognized as the key pharmacophore in several biologically active compounds. Among the major biological activities displayed by adamantane derivatives, the anti-HIV (El-Emam et al., 2004 ; Burstein et al., 1999 ; Balzarini et al., 2009 ), antibacterial (Protopopova et al., 2005 ; El-Emam et al., 2013 ; Kadi et al., 2010 ; Al-Abdullah et al., 2014 ; Al-Wahaibi et al., 2017 ), antifungal (Omar et al., 2010 ), anticancer (Sun et al., 2002 ), anti-diabetic (Villhauer et al., 2003 ; Augeri et al., 2005 ) and antimalarial (Dong et al., 2010 ) activities are the most interesting. In addition, 1,3,4-oxadiazole derivatives occupy a unique place in the field of medicinal chemistry as pharmacophores or auxophores possessing diverse pharmacological activities including antibacterial (Prakash et al., 2010 ; Ogata et al., 1971 ; Kadi et al., 2007 ), anticancer (Zhang et al., 2014 ), antiviral (Wu et al., 2015 ) and anti-inflammatory (Bansal et al., 2014 ) activities. We report herein on the crystal structure determinations of the title adamantane-oxadiazole hybrid molecules 2-(adamantan-1-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole (I) and 2-(adamantan-1-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole (II). The crystal structure of the 4-bromophenyl derivative has been reported previously (Alzoman et al., 2014 ), and after examination of the deposited CIF and transformation of the space group, from P2₁/c to P2₁/n, it is found to be isotypic with compound (II).

2. Structural commentary

Compounds (I) and (II), are built up from a central 1,3,4-oxadiazole unit, an adamantane unit and a halogenophenyl group (Figs. 1 and 2, respectively). The C—N bonds in the oxadiazole rings have double-bond character [C7=N1 = 1.279 (5) and 1.292 (3) Å, and C8=N2 = 1.288 (5) and 1.288 (3) Å in (I) and (II), respectively], while the N—N and C—O bonds exhibit single-bond character [N1—N2 = 1.408 (4) and 1.417 (3) Å, C7—O1 = 1.366 (4) and 1.360 (2) Å, and C8—O1 = 1.369 (4) and 1.359 (2) Å in (I) and (II), respectively]. These geometrical parameters are very similar to those observed for similar compounds; see §5. Database survey.

Figure 1
Molecular structure of compound (I)

, with the atom labelling and displacement ellipsoids drawn at the 50% probability level.

Figure 2
Molecular structure of compound (II)

, with the atom labelling and displacement ellipsoids drawn at the 50% probability level.

As seen in Fig. 3, the molecular structures of compounds (I) and (II) are very similar. The largest difference is highlighted by the structural overlay plot, and comes from the relative orientation of the halogenophenyl group with respect to the oxadiazole ring. In compound (II), the rings are almost coplanar with their mean planes being inclined to each other by 9.5 (1)°, while in compound (I) the equivalent dihedral angle is 20.8 (2)°.

Figure 3
View of the structural overlay of compounds (I)

and (II)

. Compound (I)

is drawn according to element type, while compound (II)

is drawn in pale green.

3. Supramolecular features

In the crystals of both compounds, molecules are linked by pairs of C—H⋯N hydrogen bonds, forming inversion dimers with R₂²(12) ring motifs (Tables 1 and 2, respectively). In the crystal of (I), the dimers are connected by C—H⋯F interactions, forming slabs lying parallel to the bc plane (Fig. 4 and Table 1). In the crystal of (II), the dimers are linked by C—H⋯π and offset π–π interactions, forming layers lying parallel to the (10 $[\overline{1}]$ ) plane; see Fig. 5 and Table 2. The offset π–π interactions involve inversion-related 4-chlorophenyl rings (C1–C6) with an intercentroid distance of 3.687 (1) Å, an interplanar distance of 3.404 (1) Å, and an offset of 1.418 Å. In Fig. 5 these interactions are represented by double-headed red arrows.

Table 1
Hydrogen-bond geometry (Å, °) for (I)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1ⁱ	0.95	2.56	3.383 (5)	146
C18—H18A⋯F1ⁱⁱ	0.99	2.47	3.415 (5)	159
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °) for (II)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1ⁱ	0.95	2.61	3.386 (3)	139
C12—H12A⋯Cg1ⁱⁱ	0.99	2.73	3.680 (3)	160
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 4
A view along the b axis of the crystal packing of compound (I)

. The hydrogen-bonding interactions (see Table 1

) are shown as dashed lines. For clarity, only hydrogen atoms H3 and H18A have been included.

Figure 5
A view along the b axis of the crystal packing of compound (II)

, showing the C—H⋯N hydrogen bonds and the C—H⋯π interactions (see Table 2

) as dashed lines. The offset π–π interactions are indicated by double-headed red arrows. For clarity, only hydrogen atoms H3 and H12A have been included.

4. Hirshfeld surface analysis

The Hirshfeld surfaces for (I) and (II) mapped over d_norm were calculated using CrystalExplorer 17 (Turner et al., 2017 ) with the default setting of arbitrary units range. The characteristic bright-red spots near atoms H3, H18A, N1 and F1 (Fig. 6) confirm the previously mentioned C3—H3⋯N1ⁱ and C18—H18A⋯F1ⁱⁱ [symmetry codes: (i) −x + 1, −y + 1, −z + 1; (ii) −x + 1, y − $[{1\over 2}]$ , −z + $[{3\over 2}]$ ] interatomic contacts in the crystal packing of (I). As expected, the same bright-red spots are observed near atoms H3 and N1 on the Hirshfeld surface of (II); see Fig. 7. The Hirshfeld surface mapped over the shape-index property elegantly illustrates the π–π stacking and the C—H⋯π interactions observed in the crystal packing of (II). Two views are presented in Fig. 8. The π–π stacking between inversion-related 4-chlorophenyl rings (C1–C6) is indicated by the appearance of small blue regions surrounding a bright-red triangle within the six-membered ring (Fig. 8a), while the C12—H12A⋯π(C1–C6)ⁱⁱⁱ interaction [symmetry code: (iii) x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z + $[{1\over 2}]$ ] appears as a large red region within the ring (Fig. 8b).

Figure 6
A view of the Hirshfeld surface mapped over d_norm for compound (I)

over the range −0.138 to 1.364 arbitrary units.

Figure 7
A view of the Hirshfeld surface mapped over d_norm for compound (II)

over the range −0.203 to 1.273 arbitrary units.

Figure 8
Two views, (a) and (b), of the Hirshfeld surface mapped over the shape-index property for compound (II)

5. Database survey

A search of the Cambridge Structural Database (CSD, version 5.40, February 2019; Groom et al., 2016 ) for the substructure 2-(adamantan-1-yl)-1,3,4-oxadiazole gave five hits. The crystal structures of three very similar compounds were reported in the last decade, namely 2-(adamantan-1-yl)-5-(4-nitrophenyl)-1,3,4-oxadiazole (CSD refcode LAPVOP; El-Emam et al., 2012 ), which has an NO₂ group on the phenyl ring (in the para position to the oxadiazole ring), 2-(adamantan-1-yl)-5-(4-bromophenyl)-1,3,4-oxadiazole (SOSXIJ; Alzoman et al. 2014), which has a Br atom on the phenyl ring (same para position) and 2-(adamantan-1-yl)-5-(3-fluorophenyl)-1,3,4-oxadiazole (SIKKAA; Khan et al., 2012 ), with a 3-fluorophenyl substituent at position 5 on the oxadiazole ring. Two more recently reported structures are (5-(adamantan-1-yl)-1,3,4-oxadiazole-2-thiolato)triphenylphosphinegold(I) (AZECAL; Garcia et al., 2016 ) and 2-(adamantan-1-yl)-5-[2-(2-methylphenyl)-1,3-thiazol-4-yl]-1,3,4-oxadiazole (XARGEE01; Khan et al., 2016 ).

The reduced cell of SOSXIJ indicates that it is isotypic with compound (II). Compound LAPVOP resides on a mirror plane, while compound SIKKAA crystallizes with two independent molecules in the asymmetric unit. The geometrical parameters of the oxadiazole rings are similar to those reported above for the title compounds. The 4-substituted phenyl rings are inclined to the oxadiazole ring by 0.0° in LAPVOP (as it lies in a mirror plane), 3.01 and 3.31° in the two independent molecules of SIKKAA and 10.44° in SOSXIJ. In the title compounds the corresponding dihedral angle is 20.8 (2)° for compound (I) and 9.5 (1)° for compound (II).

6. Synthesis and crystallization

Compounds (I) and (II) were synthesized via condensation of adamantane-1-carboxylic acid with 4-fluorobenzohydrazide, or 4-chlorobenzohydrazide in the presence of phosphorus oxychloride, as described previously (Kadi et al., 2007). Colourless plate-like crystals of compound (I) and colourless needle-like crystals of compound (II) were obtained by slow evaporation of CHCl₃:EtOH (1:1 v:v) solutions at room temperature.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All H atoms were placed in calculated positions and treated as riding atoms: C—H = 0.95–1.00 Å with U_iso = 1.2U_eq(C).

Table 3
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₈H₁₉FN₂O	C₁₈H₁₉ClN₂O
M_r	298.35	314.80
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/n
Temperature (K)	160	160
a, b, c (Å)	18.2525 (4), 7.07855 (16), 11.2207 (2)	13.08241 (19), 6.49259 (9), 18.5129 (3)
β (°)	98.556 (2)	105.5609 (16)
V (Å³)	1433.59 (6)	1514.83 (4)
Z	4	4
Radiation type	Cu Kα	Cu Kα
μ (mm⁻¹)	0.78	2.25
Crystal size (mm)	0.18 × 0.15 × 0.02	0.33 × 0.12 × 0.08

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, Pilatus 200K	XtaLAB Synergy, Dualflex, Pilatus 200K
Absorption correction	Analytical (CrysAlis PRO; Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction Ltd., Yarnton, England.]$ )	Analytical (CrysAlis PRO; Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction Ltd., Yarnton, England.]$ )
T_min, T_max	0.921, 0.990	0.642, 0.870
No. of measured, independent and observed [I > 2σ(I)] reflections	13058, 2903, 2578	14318, 3217, 3052
R_int	0.030	0.023
(sin θ/λ)_max (Å⁻¹)	0.625	0.636

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.233, 1.23	0.061, 0.167, 1.08
No. of reflections	2903	3217
No. of parameters	199	199
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.38	0.81, −0.26
Computer programs: CrysAlis PRO (Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction Ltd., Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), Mercury (Macrae et al., 2008 ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC references: 1908204; 1908203

Crystal structure: contains datablocks I, II, Global. DOI: https://doi.org/10.1107/S2056989019004651/su5492sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019004651/su5492Isup4.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989019004651/su5492Isup4.cml

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989019004651/su5492IIsup5.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989019004651/su5492IIsup5.cml

checkCIF report

Computing details top

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

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

Crystal data top

C₁₈H₁₉FN₂O	F(000) = 632
M_r = 298.35	D_x = 1.382 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 18.2525 (4) Å	Cell parameters from 7588 reflections
b = 7.07855 (16) Å	θ = 4.9–78.5°
c = 11.2207 (2) Å	µ = 0.78 mm⁻¹
β = 98.556 (2)°	T = 160 K
V = 1433.59 (6) Å³	Plate, colourless
Z = 4	0.18 × 0.15 × 0.02 mm

Data collection top

XtaLAB Synergy, Dualflex, Pilatus 200K diffractometer	2903 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2578 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.030
Detector resolution: 5.8140 pixels mm^-1	θ_max = 74.5°, θ_min = 4.9°
ω scans	h = −22→22
Absorption correction: analytical (CrysAlisPro; Rigaku OD, 2019)	k = −8→8
T_min = 0.921, T_max = 0.990	l = −11→14
13058 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.080	H-atom parameters constrained
wR(F²) = 0.233	w = 1/[σ²(F_o²) + (0.0572P)² + 6.0123P] where P = (F_o² + 2F_c²)/3
S = 1.23	(Δ/σ)_max < 0.001
2903 reflections	Δρ_max = 0.47 e Å⁻³
199 parameters	Δρ_min = −0.38 e Å⁻³
0 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.6397 (2)	0.5834 (6)	0.8751 (3)	0.0220 (8)
C2	0.6287 (2)	0.5485 (6)	0.7528 (3)	0.0218 (8)
H2	0.669009	0.519350	0.711237	0.026*
C3	0.5568 (2)	0.5574 (5)	0.6928 (3)	0.0189 (7)
H3	0.547397	0.536452	0.608242	0.023*
C4	0.4979 (2)	0.5973 (5)	0.7558 (3)	0.0178 (7)
C5	0.5114 (2)	0.6345 (5)	0.8784 (3)	0.0201 (8)
H5	0.471482	0.664740	0.920495	0.024*
C6	0.5836 (2)	0.6276 (6)	0.9397 (3)	0.0234 (8)
H6	0.593767	0.652639	1.023700	0.028*
C7	0.42268 (19)	0.5993 (5)	0.6869 (3)	0.0188 (7)
C8	0.3054 (2)	0.5755 (5)	0.6523 (3)	0.0194 (8)
C9	0.22741 (19)	0.5532 (5)	0.6776 (3)	0.0188 (8)
C10	0.2034 (2)	0.7286 (6)	0.7450 (4)	0.0229 (8)
H10A	0.235907	0.742685	0.823383	0.027*
H10B	0.208148	0.843843	0.696746	0.027*
C11	0.1226 (2)	0.7041 (6)	0.7656 (4)	0.0249 (9)
H11	0.107002	0.816945	0.809285	0.030*
C12	0.0729 (2)	0.6855 (7)	0.6436 (4)	0.0280 (9)
H12A	0.020522	0.672769	0.656054	0.034*
H12B	0.077248	0.800506	0.594894	0.034*
C13	0.0958 (2)	0.5124 (6)	0.5766 (3)	0.0261 (9)
H13	0.063156	0.501154	0.496999	0.031*
C14	0.1769 (2)	0.5336 (6)	0.5561 (3)	0.0241 (8)
H14A	0.191844	0.421626	0.512660	0.029*
H14B	0.181982	0.646678	0.506007	0.029*
C15	0.1155 (2)	0.5267 (7)	0.8408 (4)	0.0282 (9)
H15A	0.147857	0.538200	0.919522	0.034*
H15B	0.063748	0.512872	0.855987	0.034*
C16	0.1378 (2)	0.3532 (6)	0.7743 (4)	0.0264 (9)
H16	0.132697	0.237763	0.823688	0.032*
C17	0.0881 (2)	0.3342 (6)	0.6516 (4)	0.0282 (9)
H17A	0.102861	0.221647	0.608557	0.034*
H17B	0.035805	0.318109	0.663834	0.034*
C18	0.2193 (2)	0.3748 (6)	0.7544 (4)	0.0242 (8)
H18A	0.234847	0.261751	0.712615	0.029*
H18B	0.251650	0.386012	0.833140	0.029*
F1	0.71024 (12)	0.5714 (4)	0.9363 (2)	0.0321 (6)
N1	0.40489 (17)	0.6139 (5)	0.5727 (3)	0.0237 (7)
N2	0.32721 (18)	0.5975 (5)	0.5493 (3)	0.0245 (7)
O1	0.36296 (13)	0.5751 (4)	0.7457 (2)	0.0192 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0185 (18)	0.0220 (19)	0.0239 (19)	−0.0016 (15)	−0.0015 (14)	0.0036 (15)
C2	0.0179 (17)	0.0239 (19)	0.0245 (19)	−0.0014 (15)	0.0059 (14)	0.0014 (15)
C3	0.0218 (18)	0.0180 (17)	0.0177 (17)	0.0000 (14)	0.0055 (14)	−0.0012 (13)
C4	0.0152 (16)	0.0155 (16)	0.0232 (17)	−0.0024 (13)	0.0048 (13)	0.0008 (14)
C5	0.0199 (17)	0.0201 (18)	0.0217 (18)	0.0007 (14)	0.0083 (14)	0.0003 (14)
C6	0.028 (2)	0.0220 (19)	0.0204 (18)	−0.0023 (16)	0.0029 (15)	−0.0004 (15)
C7	0.0170 (17)	0.0187 (17)	0.0220 (18)	−0.0004 (14)	0.0074 (14)	0.0000 (14)
C8	0.0182 (17)	0.0217 (19)	0.0178 (17)	0.0005 (14)	0.0014 (13)	−0.0002 (14)
C9	0.0163 (17)	0.0260 (19)	0.0141 (16)	0.0021 (14)	0.0015 (13)	0.0001 (14)
C10	0.0163 (18)	0.027 (2)	0.0257 (19)	−0.0027 (15)	0.0034 (14)	−0.0046 (16)
C11	0.0153 (17)	0.034 (2)	0.027 (2)	0.0003 (16)	0.0061 (14)	−0.0057 (17)
C12	0.0159 (18)	0.039 (2)	0.029 (2)	0.0032 (17)	0.0029 (15)	0.0023 (18)
C13	0.0170 (18)	0.041 (2)	0.0191 (18)	−0.0018 (16)	−0.0021 (14)	−0.0039 (17)
C14	0.0179 (18)	0.038 (2)	0.0161 (17)	−0.0002 (16)	0.0018 (14)	−0.0001 (16)
C15	0.0197 (18)	0.045 (3)	0.0201 (19)	−0.0023 (17)	0.0047 (14)	−0.0018 (18)
C16	0.0197 (18)	0.031 (2)	0.030 (2)	−0.0026 (16)	0.0057 (15)	0.0047 (17)
C17	0.0205 (19)	0.034 (2)	0.030 (2)	−0.0060 (17)	0.0046 (16)	−0.0061 (18)
C18	0.0211 (18)	0.029 (2)	0.0233 (19)	0.0043 (16)	0.0051 (15)	0.0048 (16)
F1	0.0198 (11)	0.0465 (16)	0.0278 (12)	−0.0006 (10)	−0.0032 (9)	0.0031 (11)
N1	0.0194 (15)	0.0318 (18)	0.0207 (16)	0.0022 (13)	0.0061 (12)	0.0008 (14)
N2	0.0202 (16)	0.0366 (19)	0.0171 (15)	0.0020 (14)	0.0044 (12)	0.0013 (14)
O1	0.0148 (12)	0.0288 (14)	0.0146 (12)	−0.0007 (10)	0.0036 (9)	−0.0009 (10)

Geometric parameters (Å, º) top

C1—C2	1.380 (5)	C11—H11	1.0000
C1—C6	1.376 (5)	C11—C12	1.532 (6)
C1—F1	1.369 (4)	C11—C15	1.529 (6)
C2—H2	0.9500	C12—H12A	0.9900
C2—C3	1.384 (5)	C12—H12B	0.9900
C3—H3	0.9500	C12—C13	1.528 (6)
C3—C4	1.400 (5)	C13—H13	1.0000
C4—C5	1.386 (5)	C13—C14	1.539 (5)
C4—C7	1.472 (5)	C13—C17	1.535 (6)
C5—H5	0.9500	C14—H14A	0.9900
C5—C6	1.394 (5)	C14—H14B	0.9900
C6—H6	0.9500	C15—H15A	0.9900
C7—N1	1.279 (5)	C15—H15B	0.9900
C7—O1	1.366 (4)	C15—C16	1.523 (6)
C8—C9	1.500 (5)	C16—H16	1.0000
C8—N2	1.288 (5)	C16—C17	1.538 (6)
C8—O1	1.369 (4)	C16—C18	1.544 (5)
C9—C10	1.550 (5)	C17—H17A	0.9900
C9—C14	1.534 (5)	C17—H17B	0.9900
C9—C18	1.548 (5)	C18—H18A	0.9900
C10—H10A	0.9900	C18—H18B	0.9900
C10—H10B	0.9900	N1—N2	1.408 (4)
C10—C11	1.537 (5)

C6—C1—C2	123.8 (4)	H12A—C12—H12B	108.2
F1—C1—C2	118.3 (3)	C13—C12—C11	109.8 (3)
F1—C1—C6	117.9 (3)	C13—C12—H12A	109.7
C1—C2—H2	121.2	C13—C12—H12B	109.7
C1—C2—C3	117.5 (3)	C12—C13—H13	109.5
C3—C2—H2	121.2	C12—C13—C14	109.6 (3)
C2—C3—H3	119.8	C12—C13—C17	109.6 (3)
C2—C3—C4	120.5 (3)	C14—C13—H13	109.5
C4—C3—H3	119.8	C17—C13—H13	109.5
C3—C4—C7	117.6 (3)	C17—C13—C14	109.3 (3)
C5—C4—C3	120.2 (3)	C9—C14—C13	109.9 (3)
C5—C4—C7	122.2 (3)	C9—C14—H14A	109.7
C4—C5—H5	120.1	C9—C14—H14B	109.7
C4—C5—C6	119.9 (3)	C13—C14—H14A	109.7
C6—C5—H5	120.1	C13—C14—H14B	109.7
C1—C6—C5	118.1 (3)	H14A—C14—H14B	108.2
C1—C6—H6	121.0	C11—C15—H15A	109.7
C5—C6—H6	121.0	C11—C15—H15B	109.7
N1—C7—C4	127.2 (3)	H15A—C15—H15B	108.2
N1—C7—O1	113.1 (3)	C16—C15—C11	110.0 (3)
O1—C7—C4	119.7 (3)	C16—C15—H15A	109.7
N2—C8—C9	127.7 (3)	C16—C15—H15B	109.7
N2—C8—O1	112.5 (3)	C15—C16—H16	109.4
O1—C8—C9	119.8 (3)	C15—C16—C17	110.1 (3)
C8—C9—C10	110.7 (3)	C15—C16—C18	108.9 (3)
C8—C9—C14	107.7 (3)	C17—C16—H16	109.4
C8—C9—C18	111.2 (3)	C17—C16—C18	109.5 (3)
C14—C9—C10	109.3 (3)	C18—C16—H16	109.4
C14—C9—C18	109.1 (3)	C13—C17—C16	109.2 (3)
C18—C9—C10	108.9 (3)	C13—C17—H17A	109.8
C9—C10—H10A	109.8	C13—C17—H17B	109.8
C9—C10—H10B	109.8	C16—C17—H17A	109.8
H10A—C10—H10B	108.3	C16—C17—H17B	109.8
C11—C10—C9	109.3 (3)	H17A—C17—H17B	108.3
C11—C10—H10A	109.8	C9—C18—H18A	109.8
C11—C10—H10B	109.8	C9—C18—H18B	109.8
C10—C11—H11	109.4	C16—C18—C9	109.6 (3)
C12—C11—C10	109.2 (3)	C16—C18—H18A	109.8
C12—C11—H11	109.4	C16—C18—H18B	109.8
C15—C11—C10	109.7 (3)	H18A—C18—H18B	108.2
C15—C11—H11	109.4	C7—N1—N2	106.2 (3)
C15—C11—C12	109.6 (3)	C8—N2—N1	106.3 (3)
C11—C12—H12A	109.7	C7—O1—C8	102.0 (3)
C11—C12—H12B	109.7

C1—C2—C3—C4	−1.1 (6)	C11—C15—C16—C17	−59.2 (4)
C2—C1—C6—C5	1.1 (6)	C11—C15—C16—C18	60.8 (4)
C2—C3—C4—C5	2.2 (6)	C12—C11—C15—C16	59.0 (4)
C2—C3—C4—C7	−178.3 (3)	C12—C13—C14—C9	59.4 (4)
C3—C4—C5—C6	−1.6 (6)	C12—C13—C17—C16	−59.5 (4)
C3—C4—C7—N1	−18.2 (6)	C14—C9—C10—C11	59.8 (4)
C3—C4—C7—O1	158.6 (3)	C14—C9—C18—C16	−59.3 (4)
C4—C5—C6—C1	0.0 (6)	C14—C13—C17—C16	60.6 (4)
C4—C7—N1—N2	176.5 (4)	C15—C11—C12—C13	−59.5 (4)
C4—C7—O1—C8	−176.9 (3)	C15—C16—C17—C13	59.3 (4)
C5—C4—C7—N1	161.3 (4)	C15—C16—C18—C9	−60.5 (4)
C5—C4—C7—O1	−22.0 (5)	C17—C13—C14—C9	−60.7 (4)
C6—C1—C2—C3	−0.5 (6)	C17—C16—C18—C9	59.9 (4)
C7—C4—C5—C6	178.9 (4)	C18—C9—C10—C11	−59.3 (4)
C7—N1—N2—C8	0.4 (4)	C18—C9—C14—C13	59.8 (4)
C8—C9—C10—C11	178.1 (3)	C18—C16—C17—C13	−60.5 (4)
C8—C9—C14—C13	−179.4 (3)	F1—C1—C2—C3	178.7 (3)
C8—C9—C18—C16	−177.9 (3)	F1—C1—C6—C5	−178.2 (3)
C9—C8—N2—N1	179.3 (4)	N1—C7—O1—C8	0.3 (4)
C9—C8—O1—C7	−179.6 (3)	N2—C8—C9—C10	−111.7 (4)
C9—C10—C11—C12	−60.3 (4)	N2—C8—C9—C14	7.7 (6)
C9—C10—C11—C15	59.8 (4)	N2—C8—C9—C18	127.1 (4)
C10—C9—C14—C13	−59.2 (4)	N2—C8—O1—C7	−0.1 (4)
C10—C9—C18—C16	59.8 (4)	O1—C7—N1—N2	−0.4 (4)
C10—C11—C12—C13	60.7 (4)	O1—C8—C9—C10	67.8 (4)
C10—C11—C15—C16	−60.9 (4)	O1—C8—C9—C14	−172.9 (3)
C11—C12—C13—C14	−60.0 (4)	O1—C8—C9—C18	−53.4 (4)
C11—C12—C13—C17	60.0 (4)	O1—C8—N2—N1	−0.2 (4)

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
C3—H3···N1ⁱ	0.95	2.56	3.383 (5)	146
C18—H18A···F1ⁱⁱ	0.99	2.47	3.415 (5)	159

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y−1/2, −z+3/2.

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

Crystal data top

C₁₈H₁₉ClN₂O	F(000) = 664
M_r = 314.80	D_x = 1.380 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 13.08241 (19) Å	Cell parameters from 11758 reflections
b = 6.49259 (9) Å	θ = 3.7–79.0°
c = 18.5129 (3) Å	µ = 2.25 mm⁻¹
β = 105.5609 (16)°	T = 160 K
V = 1514.83 (4) Å³	Needle, colourless
Z = 4	0.33 × 0.12 × 0.08 mm

Data collection top

XtaLAB Synergy, Dualflex, Pilatus 200K diffractometer	3217 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	3052 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.023
Detector resolution: 5.8140 pixels mm^-1	θ_max = 78.9°, θ_min = 3.7°
ω scans	h = −16→16
Absorption correction: analytical (CrysAlisPro; Rigaku OD, 2019)	k = −7→8
T_min = 0.642, T_max = 0.870	l = −23→23
14318 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.061	H-atom parameters constrained
wR(F²) = 0.167	w = 1/[σ²(F_o²) + (0.094P)² + 1.5575P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
3217 reflections	Δρ_max = 0.81 e Å⁻³
199 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.42626 (17)	0.6044 (4)	0.35491 (12)	0.0302 (5)
C2	0.40263 (17)	0.4056 (4)	0.37203 (12)	0.0317 (5)
H2	0.333320	0.351478	0.352048	0.038*
C3	0.48137 (17)	0.2855 (4)	0.41883 (12)	0.0279 (5)
H3	0.466239	0.148920	0.431206	0.034*
C4	0.58338 (16)	0.3685 (3)	0.44753 (11)	0.0254 (4)
C5	0.60437 (17)	0.5705 (3)	0.43076 (12)	0.0280 (5)
H5	0.672884	0.627166	0.451644	0.034*
C6	0.52611 (17)	0.6897 (4)	0.38380 (13)	0.0302 (5)
H6	0.540617	0.826921	0.371688	0.036*
C7	0.66623 (17)	0.2413 (3)	0.49555 (12)	0.0229 (4)
C8	0.81754 (16)	0.1694 (3)	0.56872 (11)	0.0238 (4)
C9	0.92972 (16)	0.2106 (3)	0.61176 (11)	0.0219 (4)
C10	0.93691 (16)	0.3930 (4)	0.66595 (12)	0.0282 (5)
H10A	0.897237	0.360738	0.703168	0.034*
H10B	0.904931	0.517124	0.637722	0.034*
C11	1.05425 (18)	0.4345 (4)	0.70636 (13)	0.0314 (5)
H11	1.059032	0.553003	0.741610	0.038*
C12	1.1016 (2)	0.2426 (4)	0.75071 (13)	0.0333 (5)
H12A	1.062078	0.209782	0.787976	0.040*
H12B	1.176566	0.268774	0.778004	0.040*
C13	1.09521 (18)	0.0597 (4)	0.69691 (13)	0.0319 (5)
H13	1.126743	−0.065180	0.726092	0.038*
C14	0.97843 (17)	0.0175 (3)	0.65594 (12)	0.0285 (5)
H14A	0.938650	−0.018439	0.692756	0.034*
H14B	0.973710	−0.100189	0.621181	0.034*
C15	1.11625 (17)	0.4853 (3)	0.64960 (14)	0.0319 (5)
H15A	1.191412	0.512639	0.676075	0.038*
H15B	1.086479	0.610423	0.621095	0.038*
C16	1.10922 (16)	0.3031 (4)	0.59555 (13)	0.0284 (5)
H16	1.149192	0.336599	0.557972	0.034*
C17	1.15702 (17)	0.1113 (4)	0.63970 (14)	0.0330 (5)
H17A	1.232475	0.136605	0.665944	0.040*
H17B	1.153464	−0.006047	0.604985	0.040*
C18	0.99249 (17)	0.2645 (3)	0.55507 (12)	0.0231 (4)
H18A	0.987062	0.149794	0.518988	0.028*
H18B	0.961848	0.389182	0.526636	0.028*
Cl1	0.32838 (4)	0.75434 (10)	0.29606 (3)	0.0384 (2)
N1	0.66468 (15)	0.0461 (3)	0.50869 (12)	0.0348 (5)
N2	0.76544 (15)	−0.0012 (3)	0.55744 (12)	0.0330 (4)
O1	0.76044 (11)	0.3299 (2)	0.53130 (8)	0.0254 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0236 (10)	0.0423 (13)	0.0245 (10)	0.0028 (9)	0.0060 (8)	0.0015 (9)
C2	0.0215 (9)	0.0424 (13)	0.0291 (10)	−0.0040 (9)	0.0036 (8)	−0.0017 (9)
C3	0.0218 (10)	0.0354 (11)	0.0263 (10)	−0.0056 (8)	0.0060 (8)	−0.0019 (8)
C4	0.0218 (9)	0.0291 (11)	0.0248 (9)	−0.0027 (8)	0.0054 (7)	−0.0014 (8)
C5	0.0232 (9)	0.0290 (11)	0.0307 (10)	−0.0028 (8)	0.0050 (8)	−0.0010 (8)
C6	0.0256 (10)	0.0341 (11)	0.0310 (11)	−0.0006 (9)	0.0077 (8)	0.0012 (9)
C7	0.0186 (9)	0.0250 (10)	0.0244 (10)	−0.0048 (7)	0.0045 (8)	−0.0021 (7)
C8	0.0236 (9)	0.0217 (10)	0.0263 (9)	−0.0011 (8)	0.0069 (8)	−0.0003 (8)
C9	0.0200 (9)	0.0223 (9)	0.0233 (9)	−0.0016 (7)	0.0055 (7)	−0.0007 (7)
C10	0.0248 (10)	0.0286 (11)	0.0303 (10)	0.0010 (8)	0.0056 (8)	−0.0073 (8)
C11	0.0292 (11)	0.0290 (11)	0.0311 (11)	−0.0009 (9)	−0.0001 (8)	−0.0078 (9)
C12	0.0294 (11)	0.0431 (14)	0.0233 (10)	−0.0022 (9)	−0.0001 (9)	0.0021 (8)
C13	0.0289 (11)	0.0258 (11)	0.0349 (11)	0.0003 (9)	−0.0018 (9)	0.0083 (9)
C14	0.0285 (10)	0.0229 (10)	0.0314 (10)	−0.0029 (8)	0.0034 (8)	0.0052 (8)
C15	0.0238 (10)	0.0234 (10)	0.0432 (12)	−0.0052 (8)	−0.0004 (9)	0.0036 (9)
C16	0.0205 (10)	0.0332 (11)	0.0322 (11)	−0.0003 (8)	0.0081 (8)	0.0056 (9)
C17	0.0251 (10)	0.0296 (11)	0.0413 (12)	0.0057 (9)	0.0036 (9)	0.0000 (9)
C18	0.0213 (9)	0.0254 (10)	0.0225 (9)	−0.0001 (7)	0.0059 (8)	0.0018 (7)
Cl1	0.0242 (3)	0.0543 (4)	0.0342 (3)	0.0096 (2)	0.0034 (2)	0.0102 (2)
N1	0.0268 (9)	0.0279 (10)	0.0437 (11)	−0.0052 (7)	−0.0007 (8)	0.0024 (8)
N2	0.0258 (9)	0.0255 (9)	0.0426 (11)	−0.0055 (7)	0.0000 (8)	0.0036 (8)
O1	0.0203 (7)	0.0236 (7)	0.0300 (7)	−0.0035 (6)	0.0030 (6)	0.0005 (6)

Geometric parameters (Å, º) top

C1—C2	1.384 (4)	C11—H11	1.0000
C1—C6	1.387 (3)	C11—C12	1.529 (3)
C1—Cl1	1.740 (2)	C11—C15	1.526 (3)
C2—H2	0.9500	C12—H12A	0.9900
C2—C3	1.393 (3)	C12—H12B	0.9900
C3—H3	0.9500	C12—C13	1.538 (3)
C3—C4	1.405 (3)	C13—H13	1.0000
C4—C5	1.391 (3)	C13—C14	1.537 (3)
C4—C7	1.460 (3)	C13—C17	1.532 (3)
C5—H5	0.9500	C14—H14A	0.9900
C5—C6	1.388 (3)	C14—H14B	0.9900
C6—H6	0.9500	C15—H15A	0.9900
C7—N1	1.292 (3)	C15—H15B	0.9900
C7—O1	1.360 (2)	C15—C16	1.536 (3)
C8—C9	1.494 (3)	C16—H16	1.0000
C8—N2	1.288 (3)	C16—C17	1.528 (3)
C8—O1	1.359 (3)	C16—C18	1.531 (3)
C9—C10	1.538 (3)	C17—H17A	0.9900
C9—C14	1.539 (3)	C17—H17B	0.9900
C9—C18	1.536 (3)	C18—H18A	0.9900
C10—H10A	0.9900	C18—H18B	0.9900
C10—H10B	0.9900	N1—N2	1.417 (3)
C10—C11	1.540 (3)

C2—C1—C6	122.0 (2)	C11—C12—C13	109.73 (18)
C2—C1—Cl1	119.56 (17)	H12A—C12—H12B	108.2
C6—C1—Cl1	118.48 (19)	C13—C12—H12A	109.7
C1—C2—H2	120.3	C13—C12—H12B	109.7
C1—C2—C3	119.4 (2)	C12—C13—H13	109.5
C3—C2—H2	120.3	C14—C13—C12	109.36 (19)
C2—C3—H3	120.3	C14—C13—H13	109.5
C2—C3—C4	119.3 (2)	C17—C13—C12	109.38 (19)
C4—C3—H3	120.3	C17—C13—H13	109.5
C3—C4—C7	119.2 (2)	C17—C13—C14	109.69 (18)
C5—C4—C3	120.1 (2)	C9—C14—H14A	109.8
C5—C4—C7	120.68 (19)	C9—C14—H14B	109.8
C4—C5—H5	119.7	C13—C14—C9	109.39 (17)
C6—C5—C4	120.6 (2)	C13—C14—H14A	109.8
C6—C5—H5	119.7	C13—C14—H14B	109.8
C1—C6—C5	118.6 (2)	H14A—C14—H14B	108.2
C1—C6—H6	120.7	C11—C15—H15A	109.8
C5—C6—H6	120.7	C11—C15—H15B	109.8
N1—C7—C4	128.6 (2)	C11—C15—C16	109.40 (18)
N1—C7—O1	112.39 (19)	H15A—C15—H15B	108.2
O1—C7—C4	119.03 (17)	C16—C15—H15A	109.8
N2—C8—C9	129.94 (19)	C16—C15—H15B	109.8
N2—C8—O1	112.47 (18)	C15—C16—H16	109.5
O1—C8—C9	117.48 (17)	C17—C16—C15	109.55 (18)
C8—C9—C10	111.42 (17)	C17—C16—H16	109.5
C8—C9—C14	110.16 (17)	C17—C16—C18	109.88 (18)
C8—C9—C18	107.76 (17)	C18—C16—C15	108.81 (17)
C10—C9—C14	109.67 (17)	C18—C16—H16	109.5
C18—C9—C10	108.65 (17)	C13—C17—H17A	109.8
C18—C9—C14	109.12 (17)	C13—C17—H17B	109.8
C9—C10—H10A	109.8	C16—C17—C13	109.39 (18)
C9—C10—H10B	109.8	C16—C17—H17A	109.8
C9—C10—C11	109.27 (17)	C16—C17—H17B	109.8
H10A—C10—H10B	108.3	H17A—C17—H17B	108.2
C11—C10—H10A	109.8	C9—C18—H18A	109.6
C11—C10—H10B	109.8	C9—C18—H18B	109.6
C10—C11—H11	109.3	C16—C18—C9	110.41 (17)
C12—C11—C10	109.02 (19)	C16—C18—H18A	109.6
C12—C11—H11	109.3	C16—C18—H18B	109.6
C15—C11—C10	110.36 (18)	H18A—C18—H18B	108.1
C15—C11—H11	109.3	C7—N1—N2	105.90 (18)
C15—C11—C12	109.41 (19)	C8—N2—N1	106.14 (18)
C11—C12—H12A	109.7	C8—O1—C7	103.10 (16)
C11—C12—H12B	109.7

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
C3—H3···N1ⁱ	0.95	2.61	3.386 (3)	139
C12—H12A···Cg1ⁱⁱ	0.99	2.73	3.680 (3)	160

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

Funding information

This work was funded by the Deanship of Scientific Research at Princess Nourah bint Abdulrahman University through the Research Group Program (grant No. RGP-1438–0010).

References

Al-Abdullah, E. S., Asiri, H. H., Lahsasni, S., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2014). Drug Des. Dev. Ther. 8, 505–518. CAS Google Scholar
Al-Wahaibi, L. H., Hassan, H. M., Abo-Kamar, A. M., Ghabbour, H. A. & El-Emam, A. A. (2017). Molecules, 22, 710, 1–12. Google Scholar
Alzoman, N. Z., El-Emam, A. A., Ghabbour, H. A., Chidan Kumar, C. S. & Fun, H.-K. (2014). Acta Cryst. E70, o1231–o1232. CSD CrossRef IUCr Journals Google Scholar
Augeri, D. J., Robl, J. A., Betebenner, D. A., Magnin, D. R., Khanna, A., Robertson, J. G., Wang, A., Simpkins, L. M., Taunk, P., Huang, Q., Han, S., Abboa-Offei, B., Cap, M., Xin, L., Tao, L., Tozzo, E., Welzel, G. E., Egan, D. M., Marcinkeviciene, J., Chang, S. Y., Biller, S. A., Kirby, M. S., Parker, R. A. & Hamann, L. G. (2005). J. Med. Chem. 48, 5025–5037. Web of Science CrossRef PubMed CAS Google Scholar
Balzarini, J., Orzeszko-Krzesińska, B., Maurin, J. K. & Orzeszko, A. (2009). Eur. J. Med. Chem. 44, 303–311. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bansal, S., Bala, M., Suthar, S. K., Choudhary, S., Bhattacharya, S., Bhardwaj, V., Singla, S. & Joseph, A. (2014). Eur. J. Med. Chem. 80, 167–174. Web of Science CrossRef CAS PubMed Google Scholar
Burstein, M. E., Serbin, A. V., Khakhulina, T. V., Alymova, I. V., Stotskaya, L. L., Bogdan, O. P., Manukchina, E. E., Jdanov, V. V., Sharova, N. K. & Bukrinskaya, A. G. (1999). Antiviral Res. 41, 135–144. Web of Science CrossRef PubMed CAS Google Scholar
Davies, W. L., Grunert, R. R., Haff, R. F., Mcgahen, J. W., Neumayer, E. M., Paulshock, M., Watts, J. C., Wood, T. R., Hermann, E. C. & Hoffmann, C. E. (1964). Science, 144, 862–863. CrossRef PubMed CAS Web of Science Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Dong, Y., Wittlin, S., Sriraghavan, K., Chollet, J., Charman, S. A., Charman, W. N., Scheurer, C., Urwyler, H., Santo Tomas, J., Snyder, C., Creek, D. J., Morizzi, J., Koltun, M., Matile, H., Wang, X., Padmanilayam, M., Tang, Y., Dorn, A., Brun, R. & Vennerstrom, J. L. (2010). J. Med. Chem. 53, 481–491. CrossRef PubMed CAS Google Scholar
El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107–5113. Web of Science CrossRef PubMed CAS Google Scholar
El-Emam, A. A., Al-Tamimi, A.-S., Al-Omar, M. A., Alrashood, K. A. & Habib, E. E. (2013). Eur. J. Med. Chem. 68, 96–102. Web of Science CAS PubMed Google Scholar
El-Emam, A. A., Kadi, A. A., El-Brollosy, N. R., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o795. CSD CrossRef IUCr Journals Google Scholar
Garcia, A., Machado, R. C., Grazul, R. M., Lopes, M. T. P., Corrêa, C. C., Dos Santos, H. F., de Almeida, M. V. & Silva, H. (2016). J. Biol. Inorg. Chem. 21, 275–292. CSD CrossRef CAS PubMed Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
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. Web of Science CrossRef CAS PubMed Google Scholar
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. Web of Science CrossRef PubMed CAS Google Scholar
Khan, M., Akhtar, T., Al-Masoudi, N. A., Stoeckli-Evans, H. & Hameed, S. (2012). Med. Chem. 8, 1190–1197. CAS PubMed Google Scholar
Khan, M., Hameed, S., Akhtar, T., Al-Masoudi, N. A., Al-Masoudi, W. A., Jones, P. G. & Pannecouque, C. (2016). Med. Chem. Res. 25, 2399–2409. CSD CrossRef CAS Google Scholar
Lamoureux, G. & Artavia, G. (2010). Curr. Med. Chem. 17, 2967–2978. Web of Science CrossRef CAS PubMed Google Scholar
Liu, J., Obando, D., Liao, V., Lifa, T. & Codd, R. (2011). Eur. J. Med. Chem. 46, 1949–1963. Web of Science CrossRef CAS PubMed Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ogata, M., Atobe, H., Kushida, H. & Yamamoto, K. (1971). J. Antibiot. 24, 443–451. CrossRef CAS PubMed Web of Science Google Scholar
Omar, K., Geronikaki, A., Zoumpoulakis, P., Camoutsis, C., Soković, M., Ćirić, A. & Glamočlija, J. (2010). Bioorg. Med. Chem. 18, 426–432. Web of Science CrossRef PubMed CAS Google Scholar
Prakash, O., Kumar, M., Kumar, R., Sharma, C. & Aneja, K. R. (2010). Eur. J. Med. Chem. 45, 4252–4257. Web of Science CrossRef CAS PubMed Google Scholar
Protopopova, M., Hanrahan, C., Nikonenko, B., Samala, R., Chen, P., Gearhart, J., Einck, L. & Nacy, C. A. (2005). J. Antimicrob. Chemother. 56, 968–974. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction Ltd., Yarnton, England. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sun, S. Y., Yue, P., Chen, X., Hong, W. K. & Lotan, R. (2002). Cancer Res. 62, 2430–2436. Web of Science PubMed CAS Google Scholar
Togo, Y., Hornick, R. B. & Dawkins, A. T. (1968). J. Am. Med. Assoc. 203, 1089–1094. CrossRef CAS Google Scholar
Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17. University of Western Australia. https://hirshfeldsurface.net Google Scholar
Villhauer, E. B., Brinkman, J. A., Naderi, G. B., Burkey, B. F., Dunning, B. E., Prasad, K., Mangold, B. L., Russell, M. E. & Hughes, T. E. (2003). J. Med. Chem. 46, 2774–2789. Web of Science CSD CrossRef PubMed CAS Google Scholar
Wanka, L., Iqbal, K. & Schreiner, P. R. (2013). Chem. Rev. 113, 3516–3604. Web of Science CrossRef CAS PubMed Google Scholar
Wu, W., Chen, Q., Tai, A., Jiang, G. & Ouyang, G. (2015). Bioorg. Med. Chem. Lett. 25, 2243–2246. Web of Science CSD CrossRef CAS PubMed Google Scholar
Zhang, K., Wang, P., Xuan, L.-N., Fu, X.-Y., Jing, F., Li, S., Liu, Y.-M. & Chen, B.-Q. (2014). Bioorg. Med. Chem. Lett. 24, 5154–5156. Web of Science CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 75| Part 5| May 2019| Pages 611-615

https://doi.org/10.1107/S2056989019004651

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structures and Hirshfeld surface analysis of 2-(adamantan-1-yl)-5-(4-fluoro­phen­yl)-1,3,4-oxa­diazole and 2-(adamantan-1-yl)-5-(4-chloro­phen­yl)-1,3,4-oxa­diazole

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Hirshfeld surface analysis

5. Database survey

6. Synthesis and crystallization

7. Refinement

Supporting information

Funding information

References

research communications

Crystal structures and Hirshfeld surface analysis of 2-(adamantan-1-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole and 2-(adamantan-1-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole

3. Supramolecular features