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

In the title compound, C₂₄H₂₀ClN₃O₃, 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) = 0.005 Å
• R factor = 0.064
• wR factor = 0.160
• Data-to-parameter ratio = 15.1

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 .....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C2

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
   5 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
   1 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).

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

Crystal data

C24H20ClN3O3	F(000) = 904
Mr = 433.88	Dx = 1.335 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 12.498 (3) Å	θ = 9–12°
b = 8.2410 (16) Å	µ = 0.21 mm^−1
c = 20.996 (4) Å	T = 293 K
β = 93.21 (3)°	Block, colourless
V = 2159.1 (7) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	2179 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 26.0°, θmin = 1.9°
ω/2θ scans	h = −15→15
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.940, Tmax = 0.980	l = 0→25
4239 measured reflections	3 standard reflections every 200 reflections
4239 independent reflections

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0613P)^2] where P = (Fo^2 + 2Fc^2)/3
4239 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. Spectroscopic analysis: ¹H NMR (CDCl₃, δ, p.p.m.): 2.21 (s, 6H), 4.88 (s, 2H), 6.93–8.24 (m, 12H), 9.98 (s, 1H).

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
Cl	0.04360 (8)	0.71767 (14)	0.09117 (5)	0.0822 (4)
O1	0.7416 (2)	0.7680 (3)	0.24146 (14)	0.0770 (8)
O2	0.73560 (17)	0.4728 (3)	0.12034 (11)	0.0575 (6)
O3	0.54566 (19)	0.1704 (3)	0.00845 (13)	0.0640 (7)
N1	0.6069 (2)	0.6423 (3)	0.18362 (13)	0.0479 (7)
H1A	0.5927	0.5788	0.1518	0.057*
N2	0.5366 (2)	0.3744 (3)	0.07537 (12)	0.0454 (7)
C1	0.4807 (3)	0.4295 (4)	0.2544 (2)	0.0767 (12)
H1B	0.4295	0.3777	0.2801	0.115*
H1C	0.5516	0.4133	0.2734	0.115*
H1D	0.4760	0.3835	0.2124	0.115*
C2	0.5589 (3)	0.9848 (4)	0.1661 (2)	0.0778 (12)
H2B	0.6149	0.9235	0.1479	0.117*
H2C	0.5897	1.0726	0.1909	0.117*
H2D	0.5116	1.0275	0.1326	0.117*
N3	0.4380 (2)	0.2218 (4)	0.00522 (16)	0.0649 (9)
C3	0.4969 (3)	0.8761 (4)	0.20834 (18)	0.0567 (9)
C4	0.4108 (3)	0.9357 (5)	0.2412 (2)	0.0718 (12)
H4A	0.3948	1.0458	0.2389	0.086*
C5	0.3496 (3)	0.8367 (6)	0.2768 (2)	0.0773 (13)
H5A	0.2930	0.8797	0.2984	0.093*
C6	0.3717 (3)	0.6746 (5)	0.28060 (18)	0.0654 (11)
H6A	0.3286	0.6075	0.3039	0.079*
C7	0.4570 (3)	0.6085 (4)	0.25037 (16)	0.0498 (9)
C8	0.5191 (2)	0.7121 (4)	0.21498 (15)	0.0444 (8)
C9	0.7102 (3)	0.6701 (4)	0.20111 (17)	0.0518 (9)
C10	0.7906 (3)	0.5688 (4)	0.16835 (17)	0.0552 (9)
H10A	0.8424	0.6385	0.1491	0.066*
H10B	0.8287	0.4990	0.1991	0.066*
C11	0.7805 (3)	0.3333 (4)	0.09962 (15)	0.0470 (8)
C12	0.8871 (3)	0.2942 (4)	0.11056 (17)	0.0569 (9)
H12A	0.9323	0.3626	0.1349	0.068*
C13	0.9266 (3)	0.1536 (5)	0.08539 (19)	0.0641 (10)
H13A	0.9986	0.1273	0.0928	0.077*
C14	0.8608 (3)	0.0519 (5)	0.0494 (2)	0.0688 (11)
H14A	0.8881	−0.0427	0.0325	0.083*
C15	0.7547 (3)	0.0902 (4)	0.03859 (18)	0.0614 (10)
H15A	0.7102	0.0204	0.0145	0.074*
C16	0.7124 (3)	0.2317 (4)	0.06301 (16)	0.0471 (8)
C17	0.5987 (3)	0.2664 (4)	0.05119 (16)	0.0459 (8)
C18	0.4382 (3)	0.3422 (4)	0.04508 (17)	0.0486 (8)
C19	0.3407 (2)	0.4326 (4)	0.05710 (16)	0.0469 (8)
C20	0.2413 (3)	0.3798 (4)	0.03375 (19)	0.0622 (10)
H20A	0.2361	0.2840	0.0104	0.075*
C21	0.1498 (3)	0.4662 (5)	0.04434 (18)	0.0609 (10)
H21A	0.0832	0.4289	0.0286	0.073*
C22	0.1580 (3)	0.6077 (5)	0.07834 (17)	0.0528 (9)
C23	0.2555 (3)	0.6620 (5)	0.10226 (17)	0.0610 (10)
H23A	0.2603	0.7575	0.1259	0.073*
C24	0.3467 (3)	0.5749 (4)	0.09128 (16)	0.0550 (9)
H24A	0.4130	0.6128	0.1072	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0606 (6)	0.0941 (8)	0.0929 (8)	0.0258 (6)	0.0137 (6)	−0.0102 (7)
O1	0.0633 (16)	0.0733 (19)	0.094 (2)	−0.0062 (15)	0.0008 (15)	−0.0344 (17)
O2	0.0503 (14)	0.0550 (15)	0.0668 (16)	0.0111 (12)	−0.0001 (12)	−0.0169 (13)
O3	0.0508 (14)	0.0511 (15)	0.0890 (19)	0.0097 (12)	−0.0053 (13)	−0.0195 (14)
N1	0.0502 (17)	0.0434 (16)	0.0504 (17)	0.0038 (14)	0.0054 (13)	−0.0070 (14)
N2	0.0428 (16)	0.0375 (16)	0.0561 (18)	0.0068 (13)	0.0036 (13)	0.0018 (13)
C1	0.086 (3)	0.056 (3)	0.089 (3)	−0.002 (2)	0.015 (2)	0.017 (2)
C2	0.105 (3)	0.046 (2)	0.083 (3)	−0.004 (2)	0.006 (3)	0.014 (2)
N3	0.0468 (18)	0.0521 (19)	0.094 (2)	0.0077 (15)	−0.0079 (16)	−0.0178 (19)
C3	0.061 (2)	0.045 (2)	0.064 (2)	0.0050 (18)	−0.0051 (19)	−0.0070 (19)
C4	0.074 (3)	0.055 (3)	0.086 (3)	0.018 (2)	−0.006 (2)	−0.019 (2)
C5	0.057 (3)	0.092 (4)	0.083 (3)	0.011 (2)	0.010 (2)	−0.034 (3)
C6	0.057 (2)	0.079 (3)	0.061 (2)	−0.005 (2)	0.0098 (19)	−0.010 (2)
C7	0.052 (2)	0.051 (2)	0.047 (2)	0.0005 (17)	0.0037 (16)	−0.0027 (17)
C8	0.0450 (19)	0.0412 (19)	0.0470 (19)	0.0036 (16)	0.0020 (15)	−0.0043 (16)
C9	0.052 (2)	0.044 (2)	0.060 (2)	−0.0030 (17)	0.0064 (18)	0.0001 (19)
C10	0.047 (2)	0.053 (2)	0.065 (2)	−0.0066 (17)	0.0059 (17)	−0.0121 (19)
C11	0.046 (2)	0.048 (2)	0.0469 (19)	0.0099 (16)	0.0070 (16)	−0.0006 (17)
C12	0.050 (2)	0.057 (2)	0.064 (2)	0.0070 (18)	0.0027 (17)	−0.005 (2)
C13	0.048 (2)	0.065 (3)	0.079 (3)	0.015 (2)	0.001 (2)	−0.002 (2)
C14	0.061 (2)	0.054 (2)	0.091 (3)	0.021 (2)	−0.002 (2)	−0.014 (2)
C15	0.058 (2)	0.044 (2)	0.082 (3)	0.0053 (18)	−0.001 (2)	−0.008 (2)
C16	0.0481 (19)	0.040 (2)	0.054 (2)	0.0056 (16)	0.0056 (16)	0.0034 (17)
C17	0.050 (2)	0.0363 (19)	0.051 (2)	−0.0009 (16)	0.0034 (16)	0.0020 (16)
C18	0.046 (2)	0.038 (2)	0.062 (2)	0.0011 (16)	−0.0021 (17)	0.0032 (18)
C19	0.0406 (19)	0.043 (2)	0.057 (2)	0.0037 (16)	0.0005 (16)	0.0043 (17)
C20	0.051 (2)	0.049 (2)	0.086 (3)	0.0005 (18)	−0.003 (2)	−0.013 (2)
C21	0.0401 (19)	0.062 (3)	0.080 (3)	0.0014 (18)	−0.0036 (18)	−0.005 (2)
C22	0.048 (2)	0.058 (2)	0.053 (2)	0.0120 (18)	0.0060 (17)	0.0017 (19)
C23	0.062 (2)	0.057 (2)	0.064 (2)	0.0098 (19)	−0.0023 (19)	−0.011 (2)
C24	0.048 (2)	0.056 (2)	0.059 (2)	0.0086 (18)	−0.0071 (17)	−0.0059 (19)

Geometric parameters (Å, º)

Cl—C22	1.727 (3)	C6—H6A	0.9300
O1—C9	1.219 (4)	C7—C8	1.395 (4)
O2—C11	1.362 (4)	C9—C10	1.503 (4)
O2—C10	1.427 (4)	C10—H10A	0.9700
C17—O3	1.343 (4)	C10—H10B	0.9700
N3—O3	1.408 (3)	C11—C12	1.377 (4)
N1—C9	1.341 (4)	C11—C16	1.394 (5)
N1—C8	1.432 (4)	C12—C13	1.377 (5)
N1—H1A	0.8600	C12—H12A	0.9300
C17—N2	1.303 (4)	C13—C14	1.371 (5)
C18—N2	1.378 (4)	C13—H13A	0.9300
C1—C7	1.506 (5)	C14—C15	1.370 (5)
C1—H1B	0.9600	C14—H14A	0.9300
C1—H1C	0.9600	C15—C16	1.390 (4)
C1—H1D	0.9600	C15—H15A	0.9300
C2—C3	1.505 (5)	C16—C17	1.457 (4)
C2—H2B	0.9600	C18—C19	1.462 (4)
C2—H2C	0.9600	C19—C24	1.374 (5)
C2—H2D	0.9600	C19—C20	1.380 (4)
C18—N3	1.298 (4)	C20—C21	1.376 (4)
C3—C8	1.385 (4)	C20—H20A	0.9300
C3—C4	1.399 (5)	C21—C22	1.368 (5)
C4—C5	1.369 (5)	C21—H21A	0.9300
C4—H4A	0.9300	C22—C23	1.367 (5)
C5—C6	1.365 (5)	C23—C24	1.377 (4)
C5—H5A	0.9300	C23—H23A	0.9300
C6—C7	1.383 (5)	C24—H24A	0.9300
C11—O2—C10	120.2 (3)	C9—C10—H10B	109.9
C17—O3—N3	106.8 (2)	H10A—C10—H10B	108.3
C9—N1—C8	123.8 (3)	O2—C11—C12	123.8 (3)
C9—N1—H1A	118.1	O2—C11—C16	115.7 (3)
C8—N1—H1A	118.1	C12—C11—C16	120.5 (3)
C17—N2—C18	103.0 (3)	C13—C12—C11	119.8 (3)
C7—C1—H1B	109.5	C13—C12—H12A	120.1
C7—C1—H1C	109.5	C11—C12—H12A	120.1
H1B—C1—H1C	109.5	C14—C13—C12	120.6 (3)
C7—C1—H1D	109.5	C14—C13—H13A	119.7
H1B—C1—H1D	109.5	C12—C13—H13A	119.7
H1C—C1—H1D	109.5	C15—C14—C13	119.8 (3)
C3—C2—H2B	109.5	C15—C14—H14A	120.1
C3—C2—H2C	109.5	C13—C14—H14A	120.1
H2B—C2—H2C	109.5	C14—C15—C16	121.1 (3)
C3—C2—H2D	109.5	C14—C15—H15A	119.5
H2B—C2—H2D	109.5	C16—C15—H15A	119.5
H2C—C2—H2D	109.5	C15—C16—C11	118.3 (3)
C18—N3—O3	103.4 (3)	C15—C16—C17	119.3 (3)
C8—C3—C4	116.6 (4)	C11—C16—C17	122.4 (3)
C8—C3—C2	122.2 (3)	N2—C17—O3	112.3 (3)
C4—C3—C2	121.2 (3)	N2—C17—C16	131.6 (3)
C5—C4—C3	121.9 (4)	O3—C17—C16	116.0 (3)
C5—C4—H4A	119.0	N3—C18—N2	114.4 (3)
C3—C4—H4A	119.0	N3—C18—C19	122.0 (3)
C6—C5—C4	119.8 (4)	N2—C18—C19	123.6 (3)
C6—C5—H5A	120.1	C24—C19—C20	118.4 (3)
C4—C5—H5A	120.1	C24—C19—C18	120.2 (3)
C5—C6—C7	121.1 (4)	C20—C19—C18	121.3 (3)
C5—C6—H6A	119.4	C21—C20—C19	121.3 (3)
C7—C6—H6A	119.4	C21—C20—H20A	119.4
C6—C7—C8	118.0 (3)	C19—C20—H20A	119.4
C6—C7—C1	120.9 (3)	C22—C21—C20	119.1 (3)
C8—C7—C1	121.1 (3)	C22—C21—H21A	120.4
C3—C8—C7	122.4 (3)	C20—C21—H21A	120.4
C3—C8—N1	120.0 (3)	C23—C22—C21	120.7 (3)
C7—C8—N1	117.5 (3)	C23—C22—Cl	120.0 (3)
O1—C9—N1	124.8 (3)	C21—C22—Cl	119.3 (3)
O1—C9—C10	119.2 (3)	C22—C23—C24	119.8 (3)
N1—C9—C10	115.9 (3)	C22—C23—H23A	120.1
O2—C10—C9	108.9 (3)	C24—C23—H23A	120.1
O2—C10—H10A	109.9	C19—C24—C23	120.7 (3)
C9—C10—H10A	109.9	C19—C24—H24A	119.6
O2—C10—H10B	109.9	C23—C24—H24A	119.6
C17—O3—N3—C18	0.7 (4)	O2—C11—C16—C15	177.8 (3)
C8—C3—C4—C5	−1.8 (6)	C12—C11—C16—C15	0.6 (5)
C2—C3—C4—C5	176.1 (4)	O2—C11—C16—C17	−4.1 (5)
C3—C4—C5—C6	−0.3 (6)	C12—C11—C16—C17	178.8 (3)
C4—C5—C6—C7	1.7 (6)	C18—N2—C17—O3	−0.1 (4)
C5—C6—C7—C8	−1.0 (5)	C18—N2—C17—C16	−179.1 (3)
C5—C6—C7—C1	−179.7 (4)	N3—O3—C17—N2	−0.4 (4)
C4—C3—C8—C7	2.5 (5)	N3—O3—C17—C16	178.8 (3)
C2—C3—C8—C7	−175.3 (3)	C15—C16—C17—N2	168.7 (3)
C4—C3—C8—N1	−179.0 (3)	C11—C16—C17—N2	−9.5 (6)
C2—C3—C8—N1	3.2 (5)	C15—C16—C17—O3	−10.3 (5)
C6—C7—C8—C3	−1.2 (5)	C11—C16—C17—O3	171.5 (3)
C1—C7—C8—C3	177.5 (3)	O3—N3—C18—N2	−0.8 (4)
C6—C7—C8—N1	−179.7 (3)	O3—N3—C18—C19	−179.7 (3)
C1—C7—C8—N1	−1.0 (5)	C17—N2—C18—N3	0.6 (4)
C9—N1—C8—C3	71.1 (4)	C17—N2—C18—C19	179.5 (3)
C9—N1—C8—C7	−110.4 (4)	N3—C18—C19—C24	−169.3 (3)
C8—N1—C9—O1	−6.9 (5)	N2—C18—C19—C24	11.9 (5)
C8—N1—C9—C10	172.0 (3)	N3—C18—C19—C20	9.5 (5)
C11—O2—C10—C9	−156.7 (3)	N2—C18—C19—C20	−169.2 (3)
O1—C9—C10—O2	−175.9 (3)	C24—C19—C20—C21	−0.2 (6)
N1—C9—C10—O2	5.2 (4)	C18—C19—C20—C21	−179.1 (3)
C10—O2—C11—C12	−15.8 (5)	C19—C20—C21—C22	0.4 (6)
C10—O2—C11—C16	167.2 (3)	C20—C21—C22—C23	−0.8 (6)
O2—C11—C12—C13	−177.2 (3)	C20—C21—C22—Cl	179.4 (3)
C16—C11—C12—C13	−0.3 (5)	C21—C22—C23—C24	1.0 (6)
C11—C12—C13—C14	0.1 (6)	Cl—C22—C23—C24	−179.3 (3)
C12—C13—C14—C15	−0.2 (6)	C20—C19—C24—C23	0.4 (5)
C13—C14—C15—C16	0.6 (6)	C18—C19—C24—C23	179.3 (3)
C14—C15—C16—C11	−0.8 (5)	C22—C23—C24—C19	−0.8 (6)
C14—C15—C16—C17	−179.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2	0.86	2.40	3.254 (4)	170
N1—H1A···O2	0.86	2.13	2.558 (3)	111
C10—H10B···O1^i	0.97	2.46	3.159 (5)	128

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