5-((Meth­oxy­imino)­{2-[(2-methyl­phen­oxy)meth­yl]phen­yl}meth­yl)-N-phenyl-1,3,4-oxa­diazol-2-amine

Sharma, D.K.; Shripanavar, C.S.; Anthal, S.; Gupta, V.K.; Kant, R.

doi:10.1107/S1600536814003821

organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o357-o358

doi:10.1107/S1600536814003821

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5-((Methoxyimino){2-[(2-methylphenoxy)methyl]phenyl}methyl)-N-phenyl-1,3,4-oxadiazol-2-amine

Devinder K. Sharma,^a Chetan S. Shripanavar,^b Sumati Anthal,^a Vivek K. Gupta ^a and Rajni Kant ^a ^*

^aPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^bNational Research Centre for Grapes, Pune 412 307, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 11 February 2014; accepted 19 February 2014; online 26 February 2014)

In the title molecule, C₂₄H₂₂N₄O₃, the plane of the oxadiazole ring forms a dihedral angle of 32.41 (12)° with that of the phenyl ring and dihedral angles of 74.51 (10) and 56.38 (10)° with the planes of the benzene rings. In the crystal, pairs of N—H⋯N hydrogen bonds link molecules into inversion dimers featuring R₂²(8) graph-set motifs.

CCDC reference: 987804

Related literature

For background information and applications of oxadiazole derivatives, see: Schnurch et al. (2006 ); Crabtree (2005 ); Venkatakrishnan et al. (2000 ); Brown et al. (1992 ). For biological activity of oxadiazole derivatives, see: Omar et al. (1996 ); Talawar et al. (1996 ); Hamad et al. (1996 ); Tully et al. (1991 ); Barry et al. (1991 ); Ladduwahetty et al. (1996 ); Borg et al. (1999 ). For standard bond lengths, see: Allen et al. (1987 ). For a related structure, see: Shang et al. (2005 ).

Experimental

Crystal data

C₂₄H₂₂N₄O₃
M_r = 414.46
Triclinic, $[P \overline 1]$
a = 7.0629 (4) Å
b = 12.5553 (9) Å
c = 13.3705 (11) Å
α = 68.321 (7)°
β = 83.678 (6)°
γ = 78.567 (6)°
V = 1079.04 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.874, T_max = 1.000
7584 measured reflections
4233 independent reflections
2679 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.121
S = 1.01
4233 reflections
286 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6′⋯N3ⁱ	0.93 (2)	1.99 (2)	2.922 (2)	174
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

CCDC reference: 987804

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814003821/lh5692sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814003821/lh5692Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814003821/lh5692Isup3.cml

checkCIF report

Comment top

Derivatives of oxadiazole systems are a growing research interest, as they are precursors to functional N-heterocyclic compounds, as well as being used in pharmaceuticals as metabolically stable surrogates and photographically active systems (Schnurch et al., 2006; Crabtree, 2005; Venkatakrishnan, et al., 2000). Symmetrical and unsymmetrical 1,3,4-oxadiazoles have been reported to be versatile compounds displaying a variety of biological effects, which include anti-inflammatory (Omar et al., 1996), antifungal (Talawar et al., 1996) and antimicrobial (Hamad et al., 1996) activities. They have been utilized as bioisosteres of the carboxamide moiety in benzodiazepine receptor agonists, muscarinic receptor agonists, NK1 receptor antagonists, and Phe–Gly peptidomimetics (Tully et al., 1991; Barry et al., 1991; Ladduwahetty et al., 1996; Borg et al., 1999). Moreover, oxadiazole derivatives have been widely used as electron-conducting and hole-blocking materials in moleculebased as well as polymeric light-emitting devices (LEDs) due to the electron-deficient and favourable electron-transport properties of the oxadiazole rings (Brown et al., 1992).

In the molecule of the title compound, Fig.1, bond lengths are in normal ranges (Allen et al., 1987) and are comparable with a related structure (Shang et al., 2005). The oxadiazole ring (O1/N3/N4/C17/C18) forms a dihedral angle of 32.41 (12)° with the phenyl ring (C19-C24) and dihedral angles 74.51 (10) and 56.38 (10)° with the benzene rings (C1-C6 and C8-C13, respectfully). In the crystal, pairs of N—H···N hydrogen bonds form inversion dimers (Fig. 2).

Related literature top

For background information and applications of oxadiazole derivatives, see: Schnurch et al. (2006); Crabtree (2005); Venkatakrishnan et al. (2000); Brown et al. (1992). For biological activity of oxadiazole derivatives, see: Omar et al. (1996); Talawar et al. (1996); Hamad et al. (1996); Tully et al. (1991); Barry et al. (1991); Ladduwahetty et al. (1996); Borg et al. (1999). For standard bond lengths, see: Allen et al. (1987). For a related structure, see: Shang et al. (2005).

Experimental top

To a suspension of 2-[(2-(methoxyimino)-2-{2-[(2-methylphenoxy)methyl]phenyl}acetyl]-*N* -phenylhydrazinecarbothioamide (2.240 g, 5 mmol) in ethanol, potassium hydroxide solution (4 N, 30 ml) was added with cooling and shaking. A solution of 10% iodine in potassium iodide was added drop wise with stirring till the color of iodine persisted. The mixture was refluxed on a water bath for 4 h, and then left to cool. The separated solid was filtered off washed with water, by the process of slow evaporation recrystallized it from methanol.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines showing and inversion dimer.

5-((Methoxyimino){2-[(2-methylphenoxy)methyl]phenyl}methyl)-N-phenyl-1,3,4-oxadiazol-2-amine top

Crystal data top

C₂₄H₂₂N₄O₃	Z = 2
M_r = 414.46	F(000) = 436
Triclinic, P1	D_x = 1.276 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0629 (4) Å	Cell parameters from 2043 reflections
b = 12.5553 (9) Å	θ = 3.9–25.8°
c = 13.3705 (11) Å	µ = 0.09 mm⁻¹
α = 68.321 (7)°	T = 293 K
β = 83.678 (6)°	Block, colourless
γ = 78.567 (6)°	0.30 × 0.20 × 0.20 mm
V = 1079.04 (13) Å³

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4233 independent reflections
Radiation source: fine-focus sealed tube	2679 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.5°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −15→13
T_min = 0.874, T_max = 1.000	l = −16→13
7584 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0476P)²] where P = (F_o² + 2F_c²)/3
4233 reflections	(Δ/σ)_max = 0.001
286 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₄H₂₂N₄O₃	γ = 78.567 (6)°
M_r = 414.46	V = 1079.04 (13) Å³
Triclinic, P1	Z = 2
a = 7.0629 (4) Å	Mo Kα radiation
b = 12.5553 (9) Å	µ = 0.09 mm⁻¹
c = 13.3705 (11) Å	T = 293 K
α = 68.321 (7)°	0.30 × 0.20 × 0.20 mm
β = 83.678 (6)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4233 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	2679 reflections with I > 2σ(I)
T_min = 0.874, T_max = 1.000	R_int = 0.023
7584 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.19 e Å⁻³
4233 reflections	Δρ_min = −0.15 e Å⁻³
286 parameters

Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
O1	0.59108 (16)	0.51331 (10)	0.15728 (10)	0.0477 (3)
O2	0.09810 (18)	0.40040 (11)	0.31402 (11)	0.0599 (4)
N5	0.2555 (2)	0.44773 (13)	0.25488 (13)	0.0503 (4)
O3	0.57360 (17)	0.21849 (12)	0.42203 (11)	0.0591 (4)
N3	0.7893 (2)	0.43994 (14)	0.04992 (13)	0.0505 (4)
C1	0.3357 (2)	0.25405 (15)	0.23721 (14)	0.0408 (4)
C2	0.4559 (3)	0.15355 (15)	0.29884 (15)	0.0443 (5)
C17	0.5374 (2)	0.41397 (15)	0.15669 (15)	0.0428 (4)
N4	0.6492 (2)	0.36807 (13)	0.09560 (13)	0.0503 (4)
C7	0.6318 (3)	0.15775 (16)	0.34995 (16)	0.0513 (5)
H7A	0.6962	0.0794	0.3887	0.062*
H7B	0.7216	0.1971	0.2949	0.062*
N6	0.8571 (2)	0.60402 (15)	0.07479 (14)	0.0549 (5)
C16	0.3681 (2)	0.37311 (15)	0.22091 (14)	0.0420 (4)
C18	0.7501 (3)	0.52194 (16)	0.09016 (15)	0.0448 (5)
C8	0.7125 (3)	0.22372 (16)	0.48381 (16)	0.0460 (5)
C9	0.9052 (3)	0.17465 (16)	0.47816 (16)	0.0514 (5)
H9	0.9485	0.1368	0.4297	0.062*
C10	1.0330 (3)	0.18281 (17)	0.54587 (18)	0.0599 (6)
H10	1.1631	0.1512	0.5419	0.072*
C15	−0.0188 (3)	0.48144 (17)	0.35618 (17)	0.0598 (5)
H15A	0.0509	0.4915	0.4089	0.090*
H15B	−0.1353	0.4527	0.3893	0.090*
H15C	−0.0510	0.5548	0.2988	0.090*
C3	0.4104 (3)	0.04676 (16)	0.31252 (17)	0.0576 (6)
H3	0.4885	−0.0206	0.3542	0.069*
C6	0.1759 (3)	0.24319 (18)	0.19236 (16)	0.0525 (5)
H6	0.0941	0.3098	0.1525	0.063*
C13	0.6458 (3)	0.28167 (17)	0.55509 (17)	0.0540 (5)
C11	0.9692 (3)	0.23681 (19)	0.61822 (18)	0.0621 (6)
H11	1.0549	0.2403	0.6646	0.074*
C12	0.7771 (3)	0.28617 (18)	0.62222 (17)	0.0607 (6)
H12	0.7349	0.3234	0.6713	0.073*
C19	0.8052 (3)	0.71032 (17)	0.09168 (16)	0.0536 (5)
C5	0.1362 (3)	0.1356 (2)	0.20575 (18)	0.0628 (6)
H5	0.0302	0.1298	0.1737	0.075*
C4	0.2533 (3)	0.0375 (2)	0.26631 (19)	0.0650 (6)
H4	0.2266	−0.0354	0.2762	0.078*
C24	0.9531 (4)	0.7683 (2)	0.08959 (18)	0.0709 (6)
H24	1.0806	0.7354	0.0798	0.085*
C22	0.7283 (6)	0.9234 (2)	0.1171 (2)	0.1028 (10)
H22	0.7021	0.9951	0.1258	0.123*
C23	0.9130 (5)	0.8743 (2)	0.1019 (2)	0.0896 (8)
H23	1.0137	0.9130	0.0997	0.108*
C20	0.6179 (3)	0.7598 (2)	0.1058 (2)	0.0837 (8)
H20	0.5165	0.7223	0.1062	0.100*
C14	0.4381 (3)	0.3382 (2)	0.5583 (2)	0.0883 (8)
H14A	0.4059	0.3956	0.4888	0.133*
H14B	0.4189	0.3748	0.6111	0.133*
H14C	0.3567	0.2802	0.5771	0.133*
C21	0.5811 (5)	0.8661 (2)	0.1194 (3)	0.1116 (10)
H21	0.4543	0.8992	0.1304	0.134*
H6'	0.975 (3)	0.5895 (19)	0.039 (2)	0.088 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0448 (7)	0.0463 (7)	0.0474 (8)	−0.0087 (6)	0.0157 (6)	−0.0156 (6)
O2	0.0570 (8)	0.0457 (8)	0.0728 (10)	−0.0148 (7)	0.0342 (7)	−0.0234 (7)
N5	0.0458 (9)	0.0449 (9)	0.0513 (11)	−0.0104 (8)	0.0191 (7)	−0.0114 (8)
O3	0.0436 (8)	0.0714 (9)	0.0732 (11)	−0.0007 (7)	−0.0062 (7)	−0.0419 (8)
N3	0.0400 (9)	0.0536 (10)	0.0539 (11)	−0.0067 (8)	0.0127 (7)	−0.0193 (9)
C1	0.0410 (10)	0.0443 (10)	0.0348 (11)	−0.0065 (8)	0.0075 (8)	−0.0144 (9)
C2	0.0458 (11)	0.0436 (11)	0.0424 (11)	−0.0060 (9)	0.0030 (8)	−0.0162 (9)
C17	0.0406 (10)	0.0390 (10)	0.0426 (12)	−0.0018 (8)	0.0049 (8)	−0.0117 (9)
N4	0.0422 (9)	0.0528 (10)	0.0534 (11)	−0.0075 (8)	0.0116 (7)	−0.0200 (8)
C7	0.0509 (12)	0.0461 (11)	0.0528 (13)	0.0024 (9)	−0.0045 (9)	−0.0178 (10)
N6	0.0481 (10)	0.0530 (10)	0.0604 (12)	−0.0149 (9)	0.0221 (8)	−0.0203 (9)
C16	0.0389 (10)	0.0398 (10)	0.0396 (11)	−0.0010 (8)	0.0043 (8)	−0.0097 (9)
C18	0.0379 (10)	0.0484 (11)	0.0395 (12)	−0.0031 (9)	0.0089 (8)	−0.0110 (9)
C8	0.0406 (11)	0.0459 (11)	0.0514 (13)	−0.0130 (9)	−0.0007 (9)	−0.0147 (9)
C9	0.0472 (11)	0.0489 (11)	0.0564 (13)	−0.0068 (9)	−0.0030 (9)	−0.0175 (10)
C10	0.0468 (12)	0.0605 (13)	0.0670 (16)	−0.0124 (10)	−0.0052 (11)	−0.0140 (12)
C15	0.0588 (13)	0.0536 (12)	0.0630 (14)	−0.0063 (10)	0.0255 (10)	−0.0256 (11)
C3	0.0673 (14)	0.0433 (11)	0.0595 (14)	−0.0084 (10)	0.0009 (11)	−0.0169 (10)
C6	0.0474 (11)	0.0636 (13)	0.0448 (12)	−0.0046 (10)	0.0010 (9)	−0.0205 (10)
C13	0.0448 (11)	0.0598 (12)	0.0638 (14)	−0.0206 (10)	0.0104 (10)	−0.0271 (11)
C11	0.0621 (14)	0.0693 (14)	0.0570 (15)	−0.0264 (12)	−0.0048 (11)	−0.0167 (12)
C12	0.0643 (14)	0.0704 (14)	0.0591 (15)	−0.0340 (12)	0.0134 (11)	−0.0297 (12)
C19	0.0650 (13)	0.0486 (12)	0.0401 (12)	−0.0123 (11)	0.0133 (9)	−0.0105 (9)
C5	0.0560 (13)	0.0876 (17)	0.0600 (15)	−0.0243 (13)	0.0056 (11)	−0.0401 (13)
C4	0.0752 (15)	0.0620 (14)	0.0699 (16)	−0.0254 (13)	0.0125 (12)	−0.0346 (13)
C24	0.0824 (16)	0.0648 (15)	0.0629 (16)	−0.0224 (13)	0.0050 (12)	−0.0170 (12)
C22	0.157 (3)	0.0627 (17)	0.089 (2)	−0.027 (2)	0.025 (2)	−0.0315 (16)
C23	0.130 (3)	0.0741 (18)	0.0700 (19)	−0.0429 (18)	0.0010 (17)	−0.0207 (15)
C20	0.0751 (17)	0.0590 (15)	0.112 (2)	−0.0109 (13)	0.0269 (14)	−0.0335 (15)
C14	0.0543 (14)	0.114 (2)	0.129 (2)	−0.0165 (14)	0.0132 (14)	−0.0842 (19)
C21	0.113 (2)	0.0676 (18)	0.140 (3)	−0.0059 (18)	0.0436 (19)	−0.0384 (19)

Geometric parameters (Å, º) top

O1—C18	1.354 (2)	C15—H15B	0.9600
O1—C17	1.377 (2)	C15—H15C	0.9600
O2—N5	1.3912 (18)	C3—C4	1.372 (3)
O2—C15	1.422 (2)	C3—H3	0.9300
N5—C16	1.287 (2)	C6—C5	1.377 (3)
O3—C8	1.3759 (19)	C6—H6	0.9300
O3—C7	1.418 (2)	C13—C12	1.382 (3)
N3—C18	1.300 (2)	C13—C14	1.501 (3)
N3—N4	1.407 (2)	C11—C12	1.380 (3)
C1—C6	1.386 (2)	C11—H11	0.9300
C1—C2	1.397 (2)	C12—H12	0.9300
C1—C16	1.489 (2)	C19—C20	1.370 (3)
C2—C3	1.382 (2)	C19—C24	1.380 (3)
C2—C7	1.501 (2)	C5—C4	1.365 (3)
C17—N4	1.284 (2)	C5—H5	0.9300
C17—C16	1.456 (2)	C4—H4	0.9300
C7—H7A	0.9700	C24—C23	1.371 (3)
C7—H7B	0.9700	C24—H24	0.9300
N6—C18	1.339 (2)	C22—C23	1.356 (4)
N6—C19	1.406 (2)	C22—C21	1.368 (4)
N6—H6'	0.93 (2)	C22—H22	0.9300
C8—C9	1.385 (2)	C23—H23	0.9300
C8—C13	1.392 (3)	C20—C21	1.383 (3)
C9—C10	1.389 (2)	C20—H20	0.9300
C9—H9	0.9300	C14—H14A	0.9600
C10—C11	1.366 (3)	C14—H14B	0.9600
C10—H10	0.9300	C14—H14C	0.9600
C15—H15A	0.9600	C21—H21	0.9300

C18—O1—C17	102.10 (15)	C4—C3—C2	121.79 (18)
N5—O2—C15	109.64 (13)	C4—C3—H3	119.1
C16—N5—O2	110.37 (14)	C2—C3—H3	119.1
C8—O3—C7	117.77 (14)	C5—C6—C1	121.23 (18)
C18—N3—N4	105.98 (15)	C5—C6—H6	119.4
C6—C1—C2	119.05 (16)	C1—C6—H6	119.4
C6—C1—C16	118.34 (15)	C12—C13—C8	117.91 (18)
C2—C1—C16	122.56 (14)	C12—C13—C14	121.1 (2)
C3—C2—C1	118.43 (16)	C8—C13—C14	120.98 (17)
C3—C2—C7	119.19 (16)	C10—C11—C12	119.67 (18)
C1—C2—C7	122.38 (16)	C10—C11—H11	120.2
N4—C17—O1	112.81 (16)	C12—C11—H11	120.2
N4—C17—C16	127.54 (17)	C11—C12—C13	121.6 (2)
O1—C17—C16	119.65 (16)	C11—C12—H12	119.2
C17—N4—N3	106.21 (14)	C13—C12—H12	119.2
O3—C7—C2	108.75 (15)	C20—C19—C24	119.4 (2)
O3—C7—H7A	109.9	C20—C19—N6	123.6 (2)
C2—C7—H7A	109.9	C24—C19—N6	116.96 (19)
O3—C7—H7B	109.9	C4—C5—C6	119.65 (17)
C2—C7—H7B	109.9	C4—C5—H5	120.2
H7A—C7—H7B	108.3	C6—C5—H5	120.2
C18—N6—C19	129.13 (18)	C5—C4—C3	119.83 (19)
C18—N6—H6'	111.4 (14)	C5—C4—H4	120.1
C19—N6—H6'	118.8 (14)	C3—C4—H4	120.1
N5—C16—C17	115.10 (16)	C23—C24—C19	120.3 (2)
N5—C16—C1	126.20 (17)	C23—C24—H24	119.9
C17—C16—C1	118.63 (16)	C19—C24—H24	119.9
N3—C18—N6	125.74 (18)	C23—C22—C21	119.2 (3)
N3—C18—O1	112.89 (17)	C23—C22—H22	120.4
N6—C18—O1	121.25 (18)	C21—C22—H22	120.4
O3—C8—C9	123.67 (17)	C22—C23—C24	120.8 (3)
O3—C8—C13	115.14 (16)	C22—C23—H23	119.6
C9—C8—C13	121.19 (17)	C24—C23—H23	119.6
C8—C9—C10	119.03 (19)	C19—C20—C21	119.3 (3)
C8—C9—H9	120.5	C19—C20—H20	120.3
C10—C9—H9	120.5	C21—C20—H20	120.3
C11—C10—C9	120.60 (19)	C13—C14—H14A	109.5
C11—C10—H10	119.7	C13—C14—H14B	109.5
C9—C10—H10	119.7	H14A—C14—H14B	109.5
O2—C15—H15A	109.5	C13—C14—H14C	109.5
O2—C15—H15B	109.5	H14A—C14—H14C	109.5
H15A—C15—H15B	109.5	H14B—C14—H14C	109.5
O2—C15—H15C	109.5	C22—C21—C20	121.1 (3)
H15A—C15—H15C	109.5	C22—C21—H21	119.5
H15B—C15—H15C	109.5	C20—C21—H21	119.5

C15—O2—N5—C16	176.64 (15)	C7—O3—C8—C13	−178.30 (18)
C6—C1—C2—C3	0.1 (3)	O3—C8—C9—C10	−178.63 (18)
C16—C1—C2—C3	177.78 (18)	C13—C8—C9—C10	0.6 (3)
C6—C1—C2—C7	179.86 (17)	C8—C9—C10—C11	1.0 (3)
C16—C1—C2—C7	−2.4 (3)	C1—C2—C3—C4	0.8 (3)
C18—O1—C17—N4	−0.61 (19)	C7—C2—C3—C4	−178.94 (19)
C18—O1—C17—C16	179.83 (15)	C2—C1—C6—C5	−1.3 (3)
O1—C17—N4—N3	−0.39 (19)	C16—C1—C6—C5	−179.06 (18)
C16—C17—N4—N3	179.14 (16)	O3—C8—C13—C12	177.67 (17)
C18—N3—N4—C17	1.28 (19)	C9—C8—C13—C12	−1.7 (3)
C8—O3—C7—C2	174.85 (15)	O3—C8—C13—C14	−2.7 (3)
C3—C2—C7—O3	−120.2 (2)	C9—C8—C13—C14	177.93 (19)
C1—C2—C7—O3	60.0 (2)	C9—C10—C11—C12	−1.6 (3)
O2—N5—C16—C17	179.34 (14)	C10—C11—C12—C13	0.5 (3)
O2—N5—C16—C1	2.2 (2)	C8—C13—C12—C11	1.1 (3)
N4—C17—C16—N5	−164.43 (18)	C14—C13—C12—C11	−178.5 (2)
O1—C17—C16—N5	15.1 (2)	C18—N6—C19—C20	−14.8 (3)
N4—C17—C16—C1	12.9 (3)	C18—N6—C19—C24	167.7 (2)
O1—C17—C16—C1	−167.60 (14)	C1—C6—C5—C4	1.5 (3)
C6—C1—C16—N5	63.0 (3)	C6—C5—C4—C3	−0.6 (3)
C2—C1—C16—N5	−114.7 (2)	C2—C3—C4—C5	−0.6 (3)
C6—C1—C16—C17	−114.00 (19)	C20—C19—C24—C23	0.2 (3)
C2—C1—C16—C17	68.3 (2)	N6—C19—C24—C23	177.8 (2)
N4—N3—C18—N6	174.36 (17)	C21—C22—C23—C24	−0.4 (4)
N4—N3—C18—O1	−1.76 (19)	C19—C24—C23—C22	0.5 (4)
C19—N6—C18—N3	162.55 (19)	C24—C19—C20—C21	−1.0 (4)
C19—N6—C18—O1	−21.6 (3)	N6—C19—C20—C21	−178.5 (2)
C17—O1—C18—N3	1.49 (19)	C23—C22—C21—C20	−0.5 (5)
C17—O1—C18—N6	−174.82 (16)	C19—C20—C21—C22	1.2 (4)
C7—O3—C8—C9	1.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6′···N3ⁱ	0.93 (2)	1.99 (2)	2.922 (2)	174

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6'···N3ⁱ	0.93 (2)	1.99 (2)	2.922 (2)	174

Symmetry code: (i) −x+2, −y+1, −z.

Acknowledgements

RK acknowledges the Department of Science & Technology for the purchase of a single-crystal X-ray diffractometer sanctioned as a National Facility under Project No. SR/S2/CMP-47/2003.

References

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Volume 70| Part 3| March 2014| Pages o357-o358

doi:10.1107/S1600536814003821

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5-((Meth­­oxy­imino)­{2-[(2-methyl­phen­­oxy)meth­yl]phen­yl}meth­yl)-N-phenyl-1,3,4-oxa­diazol-2-amine

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organic compounds

5-((Methoxyimino){2-[(2-methylphenoxy)methyl]phenyl}methyl)-N-phenyl-1,3,4-oxadiazol-2-amine