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In the title compound, C24H20ClN3O3, intra­molecular N—H...N hydrogen bonds help to stabilize the mol­ecular conformation. Weak C—H...O hydrogen-bonding inter­actions result in the formation of a pseudo-dimer arranged around an inversion center.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043893/dn2079sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043893/dn2079Isup2.hkl
Contains datablock I

CCDC reference: 627494

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.065
  • wR factor = 0.179
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C4 .. 5.36 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
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 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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-(2-Chlorophenyl)-1,2,4-oxadiazol-5-yl]phenoxy}- N-(2,6-dimethylphenyl)acetamide top
Crystal data top
C24H20ClN3O3Z = 2
Mr = 433.88F(000) = 452
Triclinic, P1Dx = 1.350 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9110 (18) ÅCell parameters from 25 reflections
b = 10.612 (2) Åθ = 9–12°
c = 12.491 (3) ŵ = 0.21 mm1
α = 94.55 (3)°T = 293 K
β = 92.09 (3)°Block, colourless
γ = 114.63 (3)°0.40 × 0.30 × 0.20 mm
V = 1067.2 (5) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
2217 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 26.0°, θmin = 1.6°
ω/2θ scansh = 1010
Absorption correction: ψ scan
(North et al., 1968)
k = 1313
Tmin = 0.920, Tmax = 0.960l = 015
4169 measured reflections3 standard reflections every 200 reflections
4168 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0739P)2 + 0.0627P]
where P = (Fo2 + 2Fc2)/3
4169 reflections(Δ/σ)max < 0.001
282 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.44 e Å3
Special details top

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
xyzUiso*/Ueq
Cl0.31124 (15)0.01107 (14)0.45634 (10)0.1145 (5)
O10.1378 (3)0.1414 (2)0.1286 (2)0.0793 (7)
O20.2266 (3)0.1884 (2)0.04103 (17)0.0633 (6)
O30.3293 (3)0.5489 (2)0.00480 (18)0.0689 (7)
N10.0970 (4)0.1142 (3)0.2333 (3)0.0831 (9)
N20.1925 (3)0.0809 (3)0.1498 (2)0.0604 (7)
N30.2700 (3)0.3836 (2)0.1122 (2)0.0557 (7)
H30.23860.29600.11690.067*
C10.0148 (6)0.2605 (5)0.4120 (5)0.1078 (16)
H10.04260.31540.40410.129*
C20.0859 (7)0.2568 (6)0.5122 (5)0.1181 (19)
H20.07420.30890.57210.142*
C30.1726 (6)0.1776 (6)0.5242 (4)0.1099 (17)
H3A0.21970.17720.59170.132*
C40.1902 (5)0.0997 (4)0.4378 (4)0.0853 (12)
C50.1179 (4)0.0982 (4)0.3363 (3)0.0675 (9)
C60.0319 (5)0.1806 (4)0.3247 (4)0.0837 (11)
H60.01460.18180.25710.100*
C70.1351 (4)0.0181 (4)0.2407 (3)0.0634 (9)
C80.1933 (4)0.0201 (3)0.0840 (3)0.0578 (8)
C90.2543 (4)0.0186 (3)0.0220 (3)0.0599 (9)
C100.2985 (5)0.1234 (4)0.0622 (3)0.0769 (11)
H100.27960.19950.02380.092*
C110.3701 (5)0.1147 (5)0.1585 (4)0.0951 (14)
H110.39810.18560.18570.114*
C120.4003 (5)0.0011 (5)0.2149 (4)0.0930 (13)
H120.45210.00560.27880.112*
C130.3551 (5)0.1023 (4)0.1779 (3)0.0764 (10)
H130.37450.17760.21730.092*
C140.2808 (4)0.0944 (3)0.0823 (3)0.0606 (8)
C150.2840 (4)0.3237 (3)0.0770 (2)0.0598 (8)
H15A0.20850.32320.13510.072*
H15B0.39210.34860.10430.072*
C160.2951 (4)0.4289 (3)0.0139 (3)0.0558 (8)
C170.2924 (4)0.4721 (3)0.2088 (2)0.0521 (8)
C180.1901 (4)0.5407 (3)0.2254 (3)0.0623 (9)
C190.2195 (5)0.6293 (4)0.3188 (3)0.0768 (11)
H190.15460.67810.33020.092*
C200.3415 (6)0.6459 (4)0.3939 (3)0.0859 (12)
H200.36030.70670.45590.103*
C210.4382 (5)0.5739 (4)0.3795 (3)0.0744 (10)
H210.51910.58430.43290.089*
C220.4164 (4)0.4863 (3)0.2863 (3)0.0582 (8)
C230.0471 (5)0.5158 (4)0.1469 (3)0.0817 (11)
H23A0.02980.54400.18180.123*
H23B0.00730.41840.12160.123*
H23C0.08660.56890.08700.123*
C240.5219 (4)0.4077 (4)0.2716 (3)0.0748 (10)
H24A0.61390.44490.32500.112*
H24B0.56220.41690.20110.112*
H24C0.45710.31100.27920.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0953 (9)0.1282 (10)0.1042 (9)0.0294 (7)0.0196 (7)0.0365 (7)
O10.097 (2)0.0532 (14)0.0861 (19)0.0297 (13)0.0023 (15)0.0120 (13)
O20.0769 (16)0.0571 (13)0.0618 (14)0.0322 (12)0.0140 (12)0.0125 (11)
O30.0799 (17)0.0544 (13)0.0739 (15)0.0270 (12)0.0091 (12)0.0223 (12)
N10.101 (2)0.0575 (18)0.085 (2)0.0255 (17)0.0067 (19)0.0222 (16)
N20.0650 (18)0.0522 (15)0.0615 (17)0.0207 (14)0.0080 (14)0.0133 (14)
N30.0653 (17)0.0447 (14)0.0583 (16)0.0236 (13)0.0025 (13)0.0106 (13)
C10.087 (3)0.100 (3)0.123 (4)0.025 (3)0.040 (3)0.003 (3)
C20.090 (4)0.123 (4)0.099 (4)0.007 (3)0.039 (3)0.016 (3)
C30.079 (3)0.129 (4)0.075 (3)0.002 (3)0.012 (3)0.013 (3)
C40.066 (3)0.083 (3)0.071 (3)0.005 (2)0.011 (2)0.011 (2)
C50.058 (2)0.066 (2)0.066 (2)0.0112 (18)0.0128 (18)0.0189 (18)
C60.080 (3)0.086 (3)0.080 (3)0.029 (2)0.023 (2)0.015 (2)
C70.055 (2)0.061 (2)0.068 (2)0.0159 (17)0.0026 (17)0.0189 (18)
C80.051 (2)0.0467 (18)0.073 (2)0.0180 (15)0.0051 (17)0.0091 (17)
C90.053 (2)0.0572 (19)0.068 (2)0.0245 (16)0.0070 (17)0.0028 (17)
C100.075 (3)0.065 (2)0.093 (3)0.036 (2)0.009 (2)0.010 (2)
C110.091 (3)0.099 (3)0.107 (4)0.060 (3)0.003 (3)0.030 (3)
C120.092 (3)0.112 (3)0.081 (3)0.053 (3)0.009 (2)0.015 (3)
C130.078 (3)0.086 (3)0.065 (2)0.035 (2)0.008 (2)0.002 (2)
C140.061 (2)0.061 (2)0.060 (2)0.0276 (17)0.0026 (17)0.0048 (17)
C150.066 (2)0.0580 (19)0.0524 (19)0.0216 (17)0.0056 (16)0.0155 (16)
C160.054 (2)0.0546 (19)0.057 (2)0.0198 (16)0.0017 (15)0.0145 (16)
C170.057 (2)0.0443 (16)0.0550 (19)0.0209 (15)0.0041 (16)0.0092 (14)
C180.063 (2)0.0571 (19)0.068 (2)0.0252 (18)0.0103 (18)0.0144 (17)
C190.092 (3)0.075 (2)0.073 (3)0.045 (2)0.009 (2)0.003 (2)
C200.116 (4)0.074 (3)0.065 (2)0.042 (3)0.006 (2)0.008 (2)
C210.084 (3)0.067 (2)0.059 (2)0.020 (2)0.0081 (19)0.0077 (18)
C220.061 (2)0.0528 (18)0.059 (2)0.0207 (16)0.0030 (17)0.0161 (16)
C230.079 (3)0.086 (3)0.093 (3)0.048 (2)0.006 (2)0.011 (2)
C240.072 (2)0.080 (2)0.079 (2)0.036 (2)0.002 (2)0.022 (2)
Geometric parameters (Å, º) top
Cl—C41.721 (5)C10—H100.9300
O1—C81.347 (3)C11—C121.379 (6)
O1—N11.410 (4)C11—H110.9300
O2—C141.353 (4)C12—C131.371 (5)
O2—C151.425 (3)C12—H120.9300
O3—C161.224 (3)C13—C141.378 (5)
N1—C71.295 (4)C13—H130.9300
N2—C81.300 (4)C15—C161.498 (4)
N2—C71.369 (4)C15—H15A0.9700
N3—C161.347 (4)C15—H15B0.9700
N3—C171.422 (4)C17—C221.394 (4)
N3—H30.8600C17—C181.395 (4)
C1—C61.380 (6)C18—C191.384 (5)
C1—C21.393 (7)C18—C231.497 (5)
C1—H10.9300C19—C201.354 (5)
C2—C31.370 (7)C19—H190.9300
C2—H20.9300C20—C211.377 (5)
C3—C41.360 (6)C20—H200.9300
C3—H3A0.9300C21—C221.384 (5)
C4—C51.398 (5)C21—H210.9300
C5—C61.394 (5)C22—C241.503 (4)
C5—C71.461 (5)C23—H23A0.9600
C6—H60.9300C23—H23B0.9600
C8—C91.448 (5)C23—H23C0.9600
C9—C101.392 (4)C24—H24A0.9600
C9—C141.408 (5)C24—H24B0.9600
C10—C111.374 (6)C24—H24C0.9600
C8—O1—N1107.0 (2)C12—C13—H13120.0
C14—O2—C15120.9 (3)C14—C13—H13120.0
C7—N1—O1103.0 (3)O2—C14—C13124.4 (3)
C8—N2—C7103.4 (3)O2—C14—C9115.8 (3)
C16—N3—C17123.9 (2)C13—C14—C9119.8 (3)
C16—N3—H3118.0O2—C15—C16110.2 (2)
C17—N3—H3118.0O2—C15—H15A109.6
C6—C1—C2118.3 (5)C16—C15—H15A109.6
C6—C1—H1120.9O2—C15—H15B109.6
C2—C1—H1120.9C16—C15—H15B109.6
C3—C2—C1121.2 (5)H15A—C15—H15B108.1
C3—C2—H2119.4O3—C16—N3124.6 (3)
C1—C2—H2119.4O3—C16—C15119.0 (3)
C4—C3—C2120.5 (5)N3—C16—C15116.5 (3)
C4—C3—H3A119.8C22—C17—C18121.2 (3)
C2—C3—H3A119.8C22—C17—N3118.5 (3)
C3—C4—C5120.1 (5)C18—C17—N3120.3 (3)
C3—C4—Cl118.2 (4)C19—C18—C17118.5 (3)
C5—C4—Cl121.6 (4)C19—C18—C23120.0 (3)
C6—C5—C4119.0 (4)C17—C18—C23121.5 (3)
C6—C5—C7118.6 (4)C20—C19—C18120.7 (4)
C4—C5—C7122.4 (4)C20—C19—H19119.6
C1—C6—C5120.9 (5)C18—C19—H19119.6
C1—C6—H6119.5C19—C20—C21120.8 (4)
C5—C6—H6119.5C19—C20—H20119.6
N1—C7—N2114.8 (3)C21—C20—H20119.6
N1—C7—C5124.4 (3)C20—C21—C22120.8 (4)
N2—C7—C5120.8 (3)C20—C21—H21119.6
N2—C8—O1111.8 (3)C22—C21—H21119.6
N2—C8—C9130.5 (3)C21—C22—C17117.9 (3)
O1—C8—C9117.6 (3)C21—C22—C24120.4 (3)
C10—C9—C14119.1 (3)C17—C22—C24121.7 (3)
C10—C9—C8120.5 (3)C18—C23—H23A109.5
C14—C9—C8120.2 (3)C18—C23—H23B109.5
C11—C10—C9120.1 (4)H23A—C23—H23B109.5
C11—C10—H10119.9C18—C23—H23C109.5
C9—C10—H10119.9H23A—C23—H23C109.5
C10—C11—C12120.0 (4)H23B—C23—H23C109.5
C10—C11—H11120.0C22—C24—H24A109.5
C12—C11—H11120.0C22—C24—H24B109.5
C13—C12—C11120.9 (4)H24A—C24—H24B109.5
C13—C12—H12119.6C22—C24—H24C109.5
C11—C12—H12119.6H24A—C24—H24C109.5
C12—C13—C14120.0 (4)H24B—C24—H24C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N20.862.223.072 (3)170
N3—H3···O20.862.182.599 (3)110
C15—H15B···O3i0.972.543.223 (4)127
Symmetry code: (i) x+1, y+1, z.
 

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