Literature DB >> 22412666

2-(Adamantan-1-yl)-5-(4-nitro-phen-yl)-1,3,4-oxadiazole.

Ali A El-Emam, Adnan A Kadi, Nasser R El-Brollosy, Seik Weng Ng, Edward R T Tiekink.

Abstract

The title mol-ecule, C(18)H(19)N(3)O(3), lies on a mirror plane that bis-ects the adamantyl group. In the crystal, C-H⋯O and C-H⋯N inter-actions lead to supra-molecular chains along [100]. These assemble into layers in the ab plane via π-π inter-actions [centroid-centroid distance = 3.6548 (7) Å] between the oxadiazole and benzene rings.

Entities: CellLine Chemical Disease Gene

Year: 2012 PMID： 22412666 PMCID： PMC3297863 DOI： 10.1107/S1600536812005302

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the biological activity of adamantyl-1,3,4-oxadiazole derivatives, see: Kadi et al. (2007 ▶); El-Emam et al. (2004 ▶). For related adamantane structures, see: Al-Tamimi et al. (2010 ▶); Kadi et al. (2011 ▶).

Experimental

Crystal data

C18H19N3O3 M = 325.36 Monoclinic, a = 6.8502 (6) Å b = 6.5705 (7) Å c = 17.6761 (15) Å β = 98.432 (8)° V = 786.99 (13) Å3 Z = 2 Mo Kα radiation μ = 0.10 mm−1 T = 100 K 0.30 × 0.30 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.972, T max = 0.986 3236 measured reflections 1956 independent reflections 1456 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.123 S = 1.05 1956 reflections 136 parameters H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.34 e Å−3 Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005302/gg2074sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005302/gg2074Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812005302/gg2074Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₈H₁₉N₃O₃	F(000) = 344
M_r = 325.36	D_x = 1.373 Mg m⁻³
Monoclinic, P2₁/m	Melting point: 512 K
Hall symbol: -P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 6.8502 (6) Å	Cell parameters from 1102 reflections
b = 6.5705 (7) Å	θ = 3.0–27.5°
c = 17.6761 (15) Å	µ = 0.10 mm⁻¹
β = 98.432 (8)°	T = 100 K
V = 786.99 (13) Å³	Prism, colourless
Z = 2	0.30 × 0.30 × 0.15 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	1956 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1456 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.027
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 3.0°
ω scan	h = −8→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −8→5
T_min = 0.972, T_max = 0.986	l = −23→20
3236 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0476P)² + 0.27P] where P = (F_o² + 2F_c²)/3
1956 reflections	(Δ/σ)_max = 0.001
136 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.9944 (2)	0.2500	0.34929 (8)	0.0164 (3)
O2	1.7026 (2)	0.2500	0.67325 (10)	0.0406 (6)
O3	1.4757 (2)	0.2500	0.74600 (9)	0.0243 (4)
N1	0.6690 (3)	0.2500	0.33989 (10)	0.0178 (4)
N2	0.7505 (3)	0.2500	0.41856 (10)	0.0171 (4)
N3	1.5294 (3)	0.2500	0.68283 (11)	0.0216 (4)
C1	0.8170 (3)	0.2500	0.30226 (12)	0.0156 (4)
C2	0.8215 (3)	0.2500	0.21783 (12)	0.0148 (4)
C3	0.9314 (2)	0.4411 (2)	0.19610 (9)	0.0195 (4)
H3A	0.8624	0.5649	0.2101	0.023*
H3B	1.0672	0.4426	0.2245	0.023*
C4	0.9390 (2)	0.4400 (2)	0.10939 (9)	0.0204 (4)
H4A	1.0100	0.5642	0.0953	0.024*
C5	1.0483 (3)	0.2500	0.08863 (13)	0.0227 (5)
H5A	1.0563	0.2500	0.0332	0.027*
H5B	1.1844	0.2500	0.1168	0.027*
C6	0.6100 (3)	0.2500	0.17372 (12)	0.0184 (5)
H6A	0.5382	0.1279	0.1875	0.022*	0.50
H6B	0.5382	0.3721	0.1875	0.022*	0.50
C7	0.6192 (3)	0.2500	0.08724 (12)	0.0198 (5)
H7	0.4821	0.2500	0.0586	0.024*
C8	0.7279 (2)	0.0604 (3)	0.06587 (9)	0.0214 (4)
H8A	0.7318	0.0591	0.0101	0.026*
H8B	0.6572	−0.0632	0.0790	0.026*
C10	0.9399 (3)	0.2500	0.42055 (12)	0.0148 (4)
C11	1.0933 (3)	0.2500	0.48726 (12)	0.0148 (4)
C12	1.2920 (3)	0.2500	0.47852 (12)	0.0184 (5)
H12A	1.3293	0.2500	0.4288	0.022*
C13	1.4351 (3)	0.2500	0.54269 (13)	0.0206 (5)
H13A	1.5712	0.2500	0.5375	0.025*
C14	1.3771 (3)	0.2500	0.61451 (12)	0.0166 (5)
C15	1.1807 (3)	0.2500	0.62466 (12)	0.0163 (5)
H15A	1.1445	0.2500	0.6745	0.020*
C16	1.0384 (3)	0.2500	0.56058 (12)	0.0163 (5)
H16A	0.9026	0.2500	0.5663	0.020*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0157 (8)	0.0229 (8)	0.0104 (7)	0.000	0.0019 (6)	0.000
O2	0.0151 (9)	0.0839 (17)	0.0224 (9)	0.000	0.0019 (7)	0.000
O3	0.0265 (9)	0.0349 (10)	0.0117 (8)	0.000	0.0031 (7)	0.000
N1	0.0194 (9)	0.0220 (10)	0.0123 (9)	0.000	0.0030 (7)	0.000
N2	0.0190 (10)	0.0210 (10)	0.0115 (9)	0.000	0.0024 (7)	0.000
N3	0.0197 (10)	0.0301 (11)	0.0149 (9)	0.000	0.0025 (8)	0.000
C1	0.0162 (10)	0.0159 (10)	0.0143 (10)	0.000	0.0011 (8)	0.000
C2	0.0153 (10)	0.0186 (11)	0.0107 (9)	0.000	0.0027 (8)	0.000
C3	0.0245 (8)	0.0199 (8)	0.0142 (7)	−0.0043 (7)	0.0036 (6)	−0.0010 (6)
C4	0.0259 (8)	0.0210 (8)	0.0147 (7)	−0.0066 (7)	0.0048 (6)	0.0019 (6)
C5	0.0178 (11)	0.0383 (14)	0.0128 (10)	0.000	0.0049 (9)	0.000
C6	0.0165 (11)	0.0256 (12)	0.0131 (10)	0.000	0.0024 (9)	0.000
C7	0.0180 (11)	0.0273 (12)	0.0138 (10)	0.000	0.0008 (9)	0.000
C8	0.0291 (9)	0.0222 (8)	0.0129 (7)	−0.0049 (7)	0.0030 (7)	−0.0030 (6)
C10	0.0188 (11)	0.0149 (10)	0.0116 (10)	0.000	0.0049 (8)	0.000
C11	0.0164 (11)	0.0152 (10)	0.0127 (10)	0.000	0.0023 (8)	0.000
C12	0.0191 (11)	0.0243 (12)	0.0126 (10)	0.000	0.0049 (9)	0.000
C13	0.0152 (11)	0.0296 (13)	0.0173 (11)	0.000	0.0033 (9)	0.000
C14	0.0174 (11)	0.0185 (11)	0.0133 (10)	0.000	0.0002 (8)	0.000
C15	0.0201 (11)	0.0172 (11)	0.0125 (10)	0.000	0.0051 (8)	0.000
C16	0.0162 (11)	0.0189 (11)	0.0145 (10)	0.000	0.0042 (8)	0.000

O1—C10	1.365 (2)	C7—C8ⁱ	1.527 (2)
O1—C1	1.368 (3)	C7—C8	1.527 (2)
O2—N3	1.223 (2)	C7—H7	1.0000
O3—N3	1.226 (2)	C8—C4ⁱ	1.535 (2)
C1—N1	1.292 (3)	C8—H8A	0.9900
C1—C2	1.497 (3)	C8—H8B	0.9900
C2—C3ⁱ	1.5412 (19)	C10—N2	1.293 (3)
C2—C3	1.5412 (19)	C10—C11	1.460 (3)
C2—C6	1.542 (3)	C11—C12	1.392 (3)
C3—C4	1.541 (2)	C11—C16	1.402 (3)
C3—H3A	0.9900	C12—C13	1.386 (3)
C3—H3B	0.9900	C12—H12A	0.9500
C4—C5	1.528 (2)	C13—C14	1.385 (3)
C4—C8ⁱ	1.535 (2)	C13—H13A	0.9500
C4—H4A	1.0000	C14—C15	1.383 (3)
C5—C4ⁱ	1.528 (2)	C14—N3	1.475 (3)
C5—H5A	0.9900	C15—C16	1.382 (3)
C5—H5B	0.9900	C15—H15A	0.9500
C6—C7	1.539 (3)	C16—H16A	0.9500
C6—H6A	0.9900	N1—N2	1.421 (2)
C6—H6B	0.9900

C10—O1—C1	102.83 (16)	C8—C7—C6	109.77 (12)
N1—C1—O1	112.43 (18)	C8ⁱ—C7—H7	109.3
N1—C1—C2	130.2 (2)	C8—C7—H7	109.3
O1—C1—C2	117.35 (17)	C6—C7—H7	109.3
C1—C2—C3ⁱ	109.31 (12)	C7—C8—C4ⁱ	109.56 (14)
C1—C2—C3	109.31 (12)	C7—C8—H8A	109.8
C3ⁱ—C2—C3	109.10 (17)	C4ⁱ—C8—H8A	109.8
C1—C2—C6	110.42 (17)	C7—C8—H8B	109.8
C3ⁱ—C2—C6	109.34 (12)	C4ⁱ—C8—H8B	109.8
C3—C2—C6	109.34 (12)	H8A—C8—H8B	108.2
C4—C3—C2	109.45 (13)	N2—C10—O1	112.58 (18)
C4—C3—H3A	109.8	N2—C10—C11	128.51 (19)
C2—C3—H3A	109.8	O1—C10—C11	118.91 (18)
C4—C3—H3B	109.8	C12—C11—C16	120.1 (2)
C2—C3—H3B	109.8	C12—C11—C10	120.67 (18)
H3A—C3—H3B	108.2	C16—C11—C10	119.19 (19)
C5—C4—C8ⁱ	109.71 (14)	C13—C12—C11	119.7 (2)
C5—C4—C3	109.36 (14)	C13—C12—H12A	120.2
C8ⁱ—C4—C3	109.38 (13)	C11—C12—H12A	120.2
C5—C4—H4A	109.5	C12—C13—C14	119.1 (2)
C8ⁱ—C4—H4A	109.5	C12—C13—H13A	120.4
C3—C4—H4A	109.5	C14—C13—H13A	120.4
C4ⁱ—C5—C4	109.59 (17)	C15—C14—C13	122.3 (2)
C4ⁱ—C5—H5A	109.8	C15—C14—N3	118.57 (19)
C4—C5—H5A	109.8	C13—C14—N3	119.13 (19)
C4ⁱ—C5—H5B	109.8	C16—C15—C14	118.46 (19)
C4—C5—H5B	109.8	C16—C15—H15A	120.8
H5A—C5—H5B	108.2	C14—C15—H15A	120.8
C7—C6—C2	109.26 (17)	C15—C16—C11	120.3 (2)
C7—C6—H6A	109.8	C15—C16—H16A	119.8
C2—C6—H6A	109.8	C11—C16—H16A	119.8
C7—C6—H6B	109.8	C1—N1—N2	106.17 (18)
C2—C6—H6B	109.8	C10—N2—N1	105.99 (17)
H6A—C6—H6B	108.3	O2—N3—O3	123.5 (2)
C8ⁱ—C7—C8	109.38 (18)	O2—N3—C14	118.08 (18)
C8ⁱ—C7—C6	109.77 (12)	O3—N3—C14	118.39 (18)

C10—O1—C1—N1	0	N2—C10—C11—C12	180
C10—O1—C1—C2	180	O1—C10—C11—C12	0
N1—C1—C2—C3ⁱ	−120.32 (12)	N2—C10—C11—C16	0
O1—C1—C2—C3ⁱ	59.68 (12)	O1—C10—C11—C16	180
N1—C1—C2—C3	120.32 (12)	C16—C11—C12—C13	0
O1—C1—C2—C3	−59.68 (12)	C10—C11—C12—C13	180
N1—C1—C2—C6	0	C11—C12—C13—C14	0
O1—C1—C2—C6	180	C12—C13—C14—C15	0
C1—C2—C3—C4	179.20 (14)	C12—C13—C14—N3	180
C3ⁱ—C2—C3—C4	59.7 (2)	C13—C14—C15—C16	0
C6—C2—C3—C4	−59.83 (17)	N3—C14—C15—C16	180
C2—C3—C4—C5	−60.23 (18)	C14—C15—C16—C11	0
C2—C3—C4—C8ⁱ	59.94 (17)	C12—C11—C16—C15	0
C8ⁱ—C4—C5—C4ⁱ	−59.3 (2)	C10—C11—C16—C15	180
C3—C4—C5—C4ⁱ	60.7 (2)	O1—C1—N1—N2	0
C1—C2—C6—C7	180	C2—C1—N1—N2	180
C3ⁱ—C2—C6—C7	−59.70 (11)	O1—C10—N2—N1	0
C3—C2—C6—C7	59.70 (11)	C11—C10—N2—N1	180
C2—C6—C7—C8ⁱ	−60.13 (12)	C1—N1—N2—C10	0
C2—C6—C7—C8	60.13 (12)	C15—C14—N3—O2	180
C8ⁱ—C7—C8—C4ⁱ	60.1 (2)	C13—C14—N3—O2	0
C6—C7—C8—C4ⁱ	−60.40 (18)	C15—C14—N3—O3	0
C1—O1—C10—N2	0	C13—C14—N3—O3	180
C1—O1—C10—C11	180

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···N2ⁱⁱ	0.95	2.59	3.297 (3)	132
C16—H16A···O2ⁱⁱⁱ	0.95	2.49	3.256 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯N2ⁱ	0.95	2.59	3.297 (3)	132
C16—H16A⋯O2ⁱⁱ	0.95	2.49	3.256 (3)	137

Symmetry codes: (i) ; (ii) .

5 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles.

Authors: Adnan A Kadi; Nasser R El-Brollosy; Omar A Al-Deeb; Elsayed E Habib; Tarek M Ibrahim; Ali A El-Emam
Journal: Eur J Med Chem Date: 2006-11-28 Impact factor: 6.514

3. Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones.

Authors: Ali A El-Emam; Omar A Al-Deeb; Mohamed Al-Omar; Jochen Lehmann
Journal: Bioorg Med Chem Date: 2004-10-01 Impact factor: 3.641

4. N'-[(2-n-Butyl-4-chloro-1H-imidazol-5-yl)-methyl-idene]adamantane-1-carbo-hydrazide sesquihydrate ethanol hemi-solvate.

Authors: Abdul-Malek S Al-Tamimi; Ahmed Bari; Mohamed A Al-Omar; Ali A El-Emam; Seik Weng Ng
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-07-31

2-(Adamantan-1-yl)-5-(4-nitro-phen-yl)-1,3,4-oxadiazole.

Related literature

Experimental

Crystal data

Data collection

Refinement

1. A short history of SHELX.

2. Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles.

3. Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones.

4. N'-[(2-n-Butyl-4-chloro-1H-imidazol-5-yl)-methyl-idene]adamantane-1-carbo-hydrazide sesquihydrate ethanol hemi-solvate.

5. N'-(Adamantan-2-yl-idene)thio-phene-2-carbohydrazide.

1. 3-[(N-Methyl-anilino)meth-yl]-5-(thio-phen-2-yl)-1,3,4-oxadiazole-2(3H)-thione.

2. 2,9-Bis(5-sulfanylidene-4,5-di-hydro-1,3,4-oxa-diazol-2-yl)-1,10-phenanthroline dimethyl sulfoxide disolvate.

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

4. 5-(Adamantan-1-yl)-N-methyl-1,3,4-thia-diazol-2-amine.

5. 5-(Adamantan-1-yl)-3-[(4-benzyl-piperazin-1-yl)meth-yl]-1,3,4-oxadiazole-2(3H)-thione.