N-(2,6-Dimethyl­phen­yl)-2-{2-[3-(3-methoxy­phen­yl)-1,2,4-oxadiazol-5-yl]phen­oxy}acetamide

In the title compound, C₂₅H₂₃N₃O₄, a bifurcated intra­molecular N—H...(O,N) hydrogen bond helps to establish the mol­ecular conformation.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.169
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C19

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: PLATON (Spek, 2003).

N-(2,6-Dimethylphenyl)-2-{2-[3-(3-methoxyphenyl)-1,2,4-oxadiazol- 5-yl]phenoxy}acetamide

Crystal data

C25H23N3O4	Z = 2
Mr = 429.46	F(000) = 452
Triclinic, P1	Dx = 1.307 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0360 (16) Å	Cell parameters from 25 reflections
b = 11.692 (2) Å	θ = 9–12°
c = 12.780 (3) Å	µ = 0.09 mm^−1
α = 66.93 (3)°	T = 293 K
β = 85.56 (3)°	Block, colourless
γ = 81.18 (3)°	0.30 × 0.20 × 0.10 mm
V = 1091.5 (4) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	2740 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 26.0°, θmin = 1.7°
ω/2θ scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = −12→14
Tmin = 0.974, Tmax = 0.991	l = 0→15
4271 measured reflections	3 standard reflections every 200 reflections
4271 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0809P)^2 + 0.1494P] where P = (Fo^2 + 2Fc^2)/3
4271 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.1472 (3)	1.0792 (2)	0.35968 (18)	0.0837 (7)
O2	0.2570 (2)	1.13202 (15)	−0.11728 (15)	0.0631 (5)
O3	0.5234 (2)	0.79004 (16)	−0.07785 (15)	0.0668 (5)
O4	0.6533 (2)	0.47606 (16)	0.09651 (15)	0.0673 (5)
N1	0.1663 (3)	1.1272 (2)	−0.01782 (19)	0.0650 (6)
N2	0.2958 (2)	0.93490 (17)	0.00285 (16)	0.0480 (5)
N3	0.4544 (3)	0.62721 (18)	0.11566 (17)	0.0538 (5)
H3A	0.4142	0.7054	0.0865	0.065*
C1	−0.1885 (5)	1.2080 (3)	0.2906 (3)	0.0943 (11)
H1B	−0.2589	1.2490	0.3334	0.141*
H1C	−0.2475	1.2163	0.2250	0.141*
H1D	−0.0871	1.2462	0.2667	0.141*
C2	−0.0455 (3)	1.0053 (3)	0.3135 (2)	0.0595 (7)
C3	−0.0038 (4)	0.8816 (3)	0.3856 (3)	0.0708 (8)
H3B	−0.0452	0.8541	0.4602	0.085*
C4	0.0973 (4)	0.7995 (3)	0.3488 (2)	0.0737 (8)
H4A	0.1226	0.7160	0.3977	0.088*
C5	0.1624 (4)	0.8402 (2)	0.2386 (2)	0.0625 (7)
H5A	0.2332	0.7847	0.2139	0.075*
C6	0.1220 (3)	0.9632 (2)	0.1661 (2)	0.0489 (6)
C7	0.0161 (3)	1.0463 (2)	0.2036 (2)	0.0527 (6)
H7A	−0.0125	1.1293	0.1544	0.063*
C8	0.1937 (3)	1.0097 (2)	0.0495 (2)	0.0472 (6)
C9	0.3296 (3)	1.0141 (2)	−0.0983 (2)	0.0463 (6)
C10	0.4299 (3)	0.9977 (2)	−0.1926 (2)	0.0483 (6)
C11	0.4302 (4)	1.0973 (3)	−0.2982 (2)	0.0647 (7)
H11A	0.3660	1.1738	−0.3076	0.078*
C12	0.5234 (4)	1.0843 (3)	−0.3885 (2)	0.0747 (9)
H12A	0.5211	1.1515	−0.4585	0.090*
C13	0.6194 (4)	0.9729 (3)	−0.3756 (2)	0.0671 (8)
H13A	0.6835	0.9650	−0.4368	0.081*
C14	0.6225 (3)	0.8726 (3)	−0.2734 (2)	0.0603 (7)
H14A	0.6878	0.7969	−0.2656	0.072*
C15	0.5283 (3)	0.8841 (2)	−0.1818 (2)	0.0505 (6)
C16	0.6281 (3)	0.6747 (2)	−0.0555 (2)	0.0561 (7)
H16A	0.7452	0.6864	−0.0564	0.067*
H16B	0.6140	0.6429	−0.1134	0.067*
C17	0.5797 (3)	0.5831 (2)	0.0598 (2)	0.0525 (6)
C18	0.1096 (4)	0.5862 (3)	0.1221 (3)	0.0771 (9)
H18A	0.1732	0.6365	0.0584	0.116*
H18B	0.0134	0.6380	0.1367	0.116*
H18C	0.0726	0.5211	0.1052	0.116*
C19	0.6646 (4)	0.5266 (3)	0.3139 (2)	0.0695 (8)
H19A	0.6927	0.5805	0.2379	0.104*
H19B	0.7404	0.4495	0.3362	0.104*
H19C	0.6740	0.5673	0.3650	0.104*
C20	0.3855 (3)	0.5494 (2)	0.2217 (2)	0.0497 (6)
C21	0.4858 (3)	0.4989 (2)	0.3179 (2)	0.0522 (6)
C22	0.4162 (4)	0.4220 (2)	0.4186 (2)	0.0657 (8)
H22A	0.4815	0.3857	0.4834	0.079*
C23	0.2536 (4)	0.3985 (3)	0.4250 (3)	0.0737 (9)
H23A	0.2094	0.3466	0.4936	0.088*
C24	0.1553 (4)	0.4515 (3)	0.3298 (3)	0.0705 (8)
H24A	0.0443	0.4358	0.3354	0.085*
C25	0.2187 (3)	0.5281 (2)	0.2255 (2)	0.0561 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0891 (15)	0.0836 (15)	0.0889 (15)	−0.0107 (12)	0.0332 (12)	−0.0512 (13)
O2	0.0770 (13)	0.0479 (10)	0.0569 (11)	−0.0026 (9)	0.0088 (9)	−0.0161 (8)
O3	0.0760 (13)	0.0536 (10)	0.0528 (11)	0.0069 (9)	0.0213 (9)	−0.0110 (9)
O4	0.0779 (13)	0.0526 (11)	0.0612 (12)	0.0113 (9)	0.0083 (10)	−0.0201 (9)
N1	0.0751 (16)	0.0546 (13)	0.0633 (14)	−0.0025 (11)	0.0096 (12)	−0.0249 (11)
N2	0.0465 (11)	0.0470 (11)	0.0515 (12)	−0.0059 (9)	0.0042 (9)	−0.0213 (10)
N3	0.0576 (13)	0.0441 (11)	0.0514 (12)	0.0015 (9)	0.0110 (10)	−0.0146 (9)
C1	0.089 (2)	0.074 (2)	0.133 (3)	−0.0107 (18)	0.034 (2)	−0.062 (2)
C2	0.0552 (16)	0.0645 (17)	0.0684 (18)	−0.0120 (13)	0.0114 (13)	−0.0369 (15)
C3	0.0705 (19)	0.082 (2)	0.0620 (18)	−0.0169 (16)	0.0188 (15)	−0.0312 (16)
C4	0.084 (2)	0.0618 (18)	0.0638 (18)	−0.0048 (15)	0.0126 (16)	−0.0159 (15)
C5	0.0664 (18)	0.0561 (16)	0.0638 (17)	−0.0010 (13)	0.0084 (14)	−0.0262 (14)
C6	0.0450 (14)	0.0530 (14)	0.0548 (14)	−0.0103 (11)	−0.0001 (11)	−0.0262 (12)
C7	0.0499 (14)	0.0510 (14)	0.0613 (16)	−0.0085 (11)	0.0019 (12)	−0.0261 (12)
C8	0.0444 (13)	0.0456 (13)	0.0552 (15)	−0.0052 (10)	−0.0030 (11)	−0.0234 (12)
C9	0.0452 (13)	0.0421 (13)	0.0513 (14)	−0.0073 (10)	−0.0036 (11)	−0.0166 (11)
C10	0.0493 (14)	0.0521 (14)	0.0445 (13)	−0.0145 (11)	0.0011 (11)	−0.0173 (11)
C11	0.081 (2)	0.0553 (16)	0.0520 (16)	−0.0109 (14)	0.0009 (14)	−0.0146 (13)
C12	0.097 (2)	0.0714 (19)	0.0455 (16)	−0.0190 (18)	0.0084 (15)	−0.0103 (14)
C13	0.0727 (19)	0.083 (2)	0.0457 (15)	−0.0210 (16)	0.0137 (13)	−0.0235 (14)
C14	0.0577 (16)	0.0703 (17)	0.0524 (16)	−0.0088 (13)	0.0105 (13)	−0.0251 (14)
C15	0.0494 (14)	0.0544 (14)	0.0448 (14)	−0.0144 (11)	0.0055 (11)	−0.0146 (11)
C16	0.0575 (16)	0.0510 (14)	0.0550 (15)	0.0016 (12)	0.0109 (12)	−0.0209 (12)
C17	0.0529 (15)	0.0498 (14)	0.0540 (15)	0.0007 (12)	0.0045 (12)	−0.0229 (12)
C18	0.0565 (18)	0.093 (2)	0.076 (2)	0.0055 (16)	−0.0041 (15)	−0.0308 (17)
C19	0.0626 (18)	0.0803 (19)	0.0718 (19)	−0.0130 (15)	0.0021 (14)	−0.0355 (16)
C20	0.0512 (15)	0.0422 (12)	0.0517 (14)	−0.0009 (11)	0.0075 (12)	−0.0172 (11)
C21	0.0569 (15)	0.0464 (13)	0.0534 (15)	−0.0034 (11)	0.0044 (12)	−0.0216 (12)
C22	0.075 (2)	0.0588 (16)	0.0549 (16)	−0.0073 (14)	−0.0017 (14)	−0.0134 (13)
C23	0.079 (2)	0.0707 (19)	0.0593 (18)	−0.0219 (16)	0.0123 (16)	−0.0097 (15)
C24	0.0585 (17)	0.0694 (18)	0.079 (2)	−0.0181 (15)	0.0137 (16)	−0.0233 (16)
C25	0.0507 (15)	0.0538 (15)	0.0615 (16)	0.0011 (12)	0.0035 (12)	−0.0237 (13)

Geometric parameters (Å, º)

O1—C2	1.367 (3)	C10—C15	1.399 (3)
O1—C1	1.418 (4)	C11—C12	1.372 (4)
O2—C9	1.347 (3)	C11—H11A	0.9300
O2—N1	1.401 (3)	C12—C13	1.365 (4)
O3—C15	1.355 (3)	C12—H12A	0.9300
O3—C16	1.412 (3)	C13—C14	1.370 (4)
O4—C17	1.221 (3)	C13—H13A	0.9300
N1—C8	1.298 (3)	C14—C15	1.385 (3)
N2—C9	1.298 (3)	C14—H14A	0.9300
N2—C8	1.381 (3)	C16—C17	1.507 (3)
N3—C17	1.344 (3)	C16—H16A	0.9700
N3—C20	1.430 (3)	C16—H16B	0.9700
N3—H3A	0.8600	C18—C25	1.507 (4)
C1—H1B	0.9600	C18—H18A	0.9600
C1—H1C	0.9600	C18—H18B	0.9600
C1—H1D	0.9600	C18—H18C	0.9600
C2—C7	1.373 (4)	C19—C21	1.513 (4)
C2—C3	1.381 (4)	C19—H19A	0.9600
C3—C4	1.364 (4)	C19—H19B	0.9600
C3—H3B	0.9300	C19—H19C	0.9600
C4—C5	1.386 (4)	C20—C25	1.394 (4)
C4—H4A	0.9300	C20—C21	1.395 (4)
C5—C6	1.375 (3)	C21—C22	1.383 (4)
C5—H5A	0.9300	C22—C23	1.366 (4)
C6—C7	1.395 (3)	C22—H22A	0.9300
C6—C8	1.475 (3)	C23—C24	1.376 (4)
C7—H7A	0.9300	C23—H23A	0.9300
C9—C10	1.457 (3)	C24—C25	1.393 (4)
C10—C11	1.395 (3)	C24—H24A	0.9300
C2—O1—C1	118.0 (2)	C12—C13—H13A	119.6
C9—O2—N1	106.57 (18)	C14—C13—H13A	119.6
C15—O3—C16	120.00 (19)	C13—C14—C15	119.8 (3)
C8—N1—O2	103.75 (19)	C13—C14—H14A	120.1
C9—N2—C8	102.74 (19)	C15—C14—H14A	120.1
C17—N3—C20	122.6 (2)	O3—C15—C14	123.9 (2)
C17—N3—H3A	118.7	O3—C15—C10	115.5 (2)
C20—N3—H3A	118.7	C14—C15—C10	120.5 (2)
O1—C1—H1B	109.5	O3—C16—C17	108.33 (19)
O1—C1—H1C	109.5	O3—C16—H16A	110.0
H1B—C1—H1C	109.5	C17—C16—H16A	110.0
O1—C1—H1D	109.5	O3—C16—H16B	110.0
H1B—C1—H1D	109.5	C17—C16—H16B	110.0
H1C—C1—H1D	109.5	H16A—C16—H16B	108.4
O1—C2—C7	124.6 (3)	O4—C17—N3	124.3 (2)
O1—C2—C3	115.7 (2)	O4—C17—C16	119.7 (2)
C7—C2—C3	119.7 (2)	N3—C17—C16	116.0 (2)
C4—C3—C2	120.7 (3)	C25—C18—H18A	109.5
C4—C3—H3B	119.6	C25—C18—H18B	109.5
C2—C3—H3B	119.6	H18A—C18—H18B	109.5
C3—C4—C5	120.1 (3)	C25—C18—H18C	109.5
C3—C4—H4A	120.0	H18A—C18—H18C	109.5
C5—C4—H4A	120.0	H18B—C18—H18C	109.5
C6—C5—C4	119.7 (2)	C21—C19—H19A	109.5
C6—C5—H5A	120.2	C21—C19—H19B	109.5
C4—C5—H5A	120.2	H19A—C19—H19B	109.5
C5—C6—C7	120.0 (2)	C21—C19—H19C	109.5
C5—C6—C8	120.7 (2)	H19A—C19—H19C	109.5
C7—C6—C8	119.3 (2)	H19B—C19—H19C	109.5
C2—C7—C6	119.8 (2)	C25—C20—C21	122.3 (2)
C2—C7—H7A	120.1	C25—C20—N3	118.5 (2)
C6—C7—H7A	120.1	C21—C20—N3	119.3 (2)
N1—C8—N2	114.3 (2)	C22—C21—C20	117.8 (2)
N1—C8—C6	121.7 (2)	C22—C21—C19	120.4 (3)
N2—C8—C6	124.0 (2)	C20—C21—C19	121.9 (2)
N2—C9—O2	112.7 (2)	C23—C22—C21	121.4 (3)
N2—C9—C10	131.7 (2)	C23—C22—H22A	119.3
O2—C9—C10	115.6 (2)	C21—C22—H22A	119.3
C11—C10—C15	117.7 (2)	C22—C23—C24	120.0 (3)
C11—C10—C9	120.0 (2)	C22—C23—H23A	120.0
C15—C10—C9	122.3 (2)	C24—C23—H23A	120.0
C12—C11—C10	121.2 (3)	C23—C24—C25	121.4 (3)
C12—C11—H11A	119.4	C23—C24—H24A	119.3
C10—C11—H11A	119.4	C25—C24—H24A	119.3
C13—C12—C11	120.0 (3)	C24—C25—C20	117.1 (3)
C13—C12—H12A	120.0	C24—C25—C18	120.9 (3)
C11—C12—H12A	120.0	C20—C25—C18	122.0 (2)
C12—C13—C14	120.7 (3)
C9—O2—N1—C8	0.3 (3)	C11—C12—C13—C14	0.8 (5)
C1—O1—C2—C7	−1.8 (4)	C12—C13—C14—C15	−0.5 (4)
C1—O1—C2—C3	177.6 (3)	C16—O3—C15—C14	4.9 (4)
O1—C2—C3—C4	−179.8 (3)	C16—O3—C15—C10	−175.1 (2)
C7—C2—C3—C4	−0.4 (4)	C13—C14—C15—O3	179.9 (3)
C2—C3—C4—C5	1.4 (5)	C13—C14—C15—C10	−0.1 (4)
C3—C4—C5—C6	−1.3 (5)	C11—C10—C15—O3	−179.7 (2)
C4—C5—C6—C7	0.2 (4)	C9—C10—C15—O3	0.4 (3)
C4—C5—C6—C8	178.2 (2)	C11—C10—C15—C14	0.2 (4)
O1—C2—C7—C6	178.7 (2)	C9—C10—C15—C14	−179.7 (2)
C3—C2—C7—C6	−0.7 (4)	C15—O3—C16—C17	−172.4 (2)
C5—C6—C7—C2	0.8 (4)	C20—N3—C17—O4	−4.8 (4)
C8—C6—C7—C2	−177.2 (2)	C20—N3—C17—C16	175.1 (2)
O2—N1—C8—N2	−0.1 (3)	O3—C16—C17—O4	179.4 (2)
O2—N1—C8—C6	179.1 (2)	O3—C16—C17—N3	−0.5 (3)
C9—N2—C8—N1	−0.2 (3)	C17—N3—C20—C25	−114.2 (3)
C9—N2—C8—C6	−179.3 (2)	C17—N3—C20—C21	66.7 (3)
C5—C6—C8—N1	−175.3 (2)	C25—C20—C21—C22	2.1 (4)
C7—C6—C8—N1	2.7 (4)	N3—C20—C21—C22	−178.8 (2)
C5—C6—C8—N2	3.8 (4)	C25—C20—C21—C19	−177.6 (2)
C7—C6—C8—N2	−178.2 (2)	N3—C20—C21—C19	1.5 (3)
C8—N2—C9—O2	0.4 (3)	C20—C21—C22—C23	−1.5 (4)
C8—N2—C9—C10	−179.5 (3)	C19—C21—C22—C23	178.2 (3)
N1—O2—C9—N2	−0.4 (3)	C21—C22—C23—C24	0.1 (5)
N1—O2—C9—C10	179.4 (2)	C22—C23—C24—C25	0.9 (5)
N2—C9—C10—C11	172.6 (3)	C23—C24—C25—C20	−0.4 (4)
O2—C9—C10—C11	−7.3 (3)	C23—C24—C25—C18	−179.7 (3)
N2—C9—C10—C15	−7.5 (4)	C21—C20—C25—C24	−1.2 (4)
O2—C9—C10—C15	172.6 (2)	N3—C20—C25—C24	179.7 (2)
C15—C10—C11—C12	0.1 (4)	C21—C20—C25—C18	178.1 (2)
C9—C10—C11—C12	−180.0 (3)	N3—C20—C25—C18	−1.0 (4)
C10—C11—C12—C13	−0.7 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···N3	0.96	2.42	2.893 (4)	110
C18—H18A···N3	0.96	2.40	2.873 (4)	110
C11—H11A···O2	0.93	2.41	2.741 (3)	101
N3—H3A···N2	0.86	2.53	3.385 (3)	179
N3—H3A···O3	0.86	2.12	2.543 (3)	110