5-((Meth-oxy-imino)-{2-[(2-methyl-phen-oxy)meth-yl]phen-yl}meth-yl)-N-phenyl-1,3,4-oxa-diazol-2-amine.

In the title mol-ecule, C24H22N4O3, the plane of the oxa-diazole 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 R 2 (2)(8) graph-set motifs.

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 = 414.46

Triclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.121

S = 1.01

4233 reflections

286 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); 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.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814003821/lh5692sup1.cif

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

Click here for additional data file.

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

CCDC reference:

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

C24H22N4O3	Z = 2
Mr = 414.46	F(000) = 436
Triclinic, P1	Dx = 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

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4233 independent reflections
Radiation source: fine-focus sealed tube	2679 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −15→13
Tmin = 0.874, Tmax = 1.000	l = −16→13
7584 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) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0476P)2] where P = (Fo2 + 2Fc2)/3
4233 reflections	(Δ/σ)max = 0.001
286 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) .