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The title compound, C18H16N2O4, was synthesized by the reaction of methyl (2-hydroxy­phenyl)­acetate and 5-chloro­methyl-3-phenyl-1,2,4-oxa­diazo­le. In the crystal structure, there are weak intermolecular C—H...O hydrogen bonds and weak C—H...π(arene) interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804018458/lh6245sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804018458/lh6245Isup2.hkl
Contains datablock I

CCDC reference: 251639

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.056
  • wR factor = 0.186
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A .. CG3 .. 2.81 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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

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: SHELXL97.

Methyl {2-[(3-phenyl-1,2,4-oxadiazol-5-yl)methoxy]phenyl}acetate top
Crystal data top
C18H16N2O4Z = 2
Mr = 324.33F(000) = 340
Triclinic, P1Dx = 1.343 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7850 (18) ÅCell parameters from 25 reflections
b = 9.848 (2) Åθ = 10–13°
c = 10.345 (2) ŵ = 0.10 mm1
α = 77.90 (3)°T = 293 K
β = 79.12 (3)°Block, colourless
γ = 67.39 (3)°0.40 × 0.30 × 0.30 mm
V = 802.0 (3) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
2141 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 26.0°, θmin = 2.0°
ω/2θ scansh = 010
Absorption correction: ψ scan
(SHELXTL; Siemens, 1996)
k = 1112
Tmin = 0.963, Tmax = 0.972l = 1212
3347 measured reflections3 standard reflections every 200 reflections
3129 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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186H-atom parameters constrained
S = 1.17 w = 1/[σ2(Fo2) + (0.076P)2 + 0.34P]
where P = (Fo2 + 2Fc2)/3
3129 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.32 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
O10.2479 (3)0.4841 (2)0.1489 (2)0.0762 (7)
O20.2278 (2)0.1422 (2)0.05165 (18)0.0534 (5)
O30.1390 (2)0.0864 (3)0.3905 (2)0.0711 (7)
O40.3701 (2)0.2030 (2)0.26622 (19)0.0618 (6)
N10.1397 (4)0.5793 (3)0.2430 (3)0.0794 (9)
N20.0624 (3)0.3849 (3)0.1466 (2)0.0530 (6)
C10.2137 (5)0.7279 (4)0.5191 (4)0.0782 (10)
H1B0.21430.80410.58970.094*
C20.0981 (4)0.6836 (4)0.4302 (3)0.0694 (9)
H2B0.02140.73030.44110.083*
C30.0962 (4)0.5703 (3)0.3254 (3)0.0529 (7)
C40.2143 (4)0.5058 (3)0.3092 (3)0.0632 (8)
H4A0.21610.43110.23780.076*
C50.3303 (4)0.5515 (4)0.3986 (4)0.0739 (9)
H5A0.41000.50800.38670.089*
C60.3272 (4)0.6605 (4)0.5039 (3)0.0740 (10)
H6A0.40250.68890.56560.089*
C70.0349 (4)0.5142 (3)0.2375 (3)0.0531 (7)
C80.1926 (3)0.3738 (3)0.0985 (3)0.0486 (6)
C90.2904 (4)0.2589 (3)0.0044 (3)0.0553 (7)
H9A0.40530.21750.03370.066*
H9B0.28770.30600.07870.066*
C100.2695 (3)0.0319 (3)0.0251 (2)0.0436 (6)
C110.3642 (3)0.0286 (3)0.1483 (3)0.0491 (7)
H11A0.40310.10540.18570.059*
C120.4007 (4)0.0896 (3)0.2154 (3)0.0559 (7)
H12A0.46600.09310.29750.067*
C130.3411 (4)0.2019 (3)0.1617 (3)0.0591 (8)
H13A0.36460.28040.20790.071*
C140.2466 (4)0.1981 (3)0.0393 (3)0.0574 (8)
H14A0.20630.27440.00370.069*
C150.2106 (3)0.0829 (3)0.0315 (2)0.0463 (6)
C160.1145 (3)0.0810 (4)0.1682 (3)0.0536 (7)
H16A0.03610.01910.17540.064*
H16B0.05150.14580.18010.064*
C170.2243 (3)0.1305 (3)0.2768 (3)0.0484 (7)
C180.2333 (4)0.1292 (5)0.5027 (3)0.0835 (11)
H18A0.16050.09330.57980.125*
H18B0.31850.08680.48250.125*
H18C0.28340.23570.52020.125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0855 (16)0.0648 (14)0.0962 (17)0.0423 (12)0.0490 (14)0.0138 (12)
O20.0604 (12)0.0550 (11)0.0457 (10)0.0225 (9)0.0088 (9)0.0039 (9)
O30.0482 (11)0.1049 (17)0.0471 (12)0.0092 (11)0.0118 (9)0.0137 (11)
O40.0430 (11)0.0860 (15)0.0498 (11)0.0174 (10)0.0117 (9)0.0024 (10)
N10.093 (2)0.0656 (17)0.092 (2)0.0405 (16)0.0517 (18)0.0208 (15)
N20.0541 (14)0.0526 (13)0.0558 (14)0.0216 (11)0.0179 (11)0.0008 (11)
C10.077 (2)0.078 (2)0.063 (2)0.0115 (19)0.0255 (18)0.0093 (17)
C20.066 (2)0.071 (2)0.066 (2)0.0229 (17)0.0193 (16)0.0068 (16)
C30.0535 (16)0.0502 (15)0.0526 (16)0.0119 (13)0.0154 (13)0.0077 (13)
C40.0602 (18)0.0590 (18)0.067 (2)0.0148 (15)0.0246 (15)0.0003 (15)
C50.062 (2)0.080 (2)0.079 (2)0.0174 (17)0.0246 (17)0.0129 (19)
C60.0576 (19)0.086 (2)0.065 (2)0.0026 (18)0.0234 (16)0.0149 (19)
C70.0591 (17)0.0469 (15)0.0546 (17)0.0177 (13)0.0152 (13)0.0058 (13)
C80.0515 (15)0.0433 (14)0.0547 (16)0.0167 (12)0.0172 (12)0.0062 (12)
C90.0621 (18)0.0526 (16)0.0553 (17)0.0193 (14)0.0217 (14)0.0061 (13)
C100.0430 (14)0.0511 (15)0.0389 (13)0.0171 (12)0.0145 (11)0.0020 (11)
C110.0522 (15)0.0557 (16)0.0420 (14)0.0247 (13)0.0115 (12)0.0028 (12)
C120.0541 (17)0.076 (2)0.0391 (14)0.0255 (15)0.0057 (12)0.0076 (14)
C130.0673 (19)0.0619 (18)0.0561 (18)0.0248 (15)0.0191 (15)0.0123 (14)
C140.0680 (19)0.0625 (18)0.0523 (17)0.0355 (15)0.0191 (14)0.0034 (14)
C150.0443 (14)0.0563 (16)0.0401 (14)0.0209 (12)0.0157 (11)0.0043 (12)
C160.0438 (15)0.0716 (19)0.0456 (15)0.0264 (14)0.0105 (12)0.0063 (13)
C170.0428 (15)0.0596 (17)0.0431 (15)0.0238 (13)0.0051 (11)0.0021 (12)
C180.063 (2)0.130 (3)0.0474 (18)0.016 (2)0.0186 (15)0.0191 (19)
Geometric parameters (Å, º) top
O1—C81.326 (3)C6—H6A0.9300
O1—N11.418 (3)C8—C91.497 (4)
O2—C101.375 (3)C9—H9A0.9700
O2—C91.418 (3)C9—H9B0.9700
O3—C171.328 (3)C10—C111.383 (4)
O3—C181.450 (4)C10—C151.396 (4)
O4—C171.200 (3)C11—C121.381 (4)
N1—C71.296 (4)C11—H11A0.9300
N2—C81.291 (3)C12—C131.372 (4)
N2—C71.383 (4)C12—H12A0.9300
C1—C61.366 (5)C13—C141.376 (4)
C1—C21.383 (5)C13—H13A0.9300
C1—H1B0.9300C14—C151.382 (4)
C2—C31.381 (4)C14—H14A0.9300
C2—H2B0.9300C15—C161.504 (4)
C3—C41.380 (4)C16—C171.499 (4)
C3—C71.467 (4)C16—H16A0.9700
C4—C51.387 (4)C16—H16B0.9700
C4—H4A0.9300C18—H18A0.9600
C5—C61.364 (5)C18—H18B0.9600
C5—H5A0.9300C18—H18C0.9600
C8—O1—N1106.2 (2)H9A—C9—H9B107.9
C10—O2—C9118.2 (2)O2—C10—C11124.7 (2)
C17—O3—C18116.0 (2)O2—C10—C15114.7 (2)
C7—N1—O1103.3 (2)C11—C10—C15120.6 (2)
C8—N2—C7102.5 (2)C12—C11—C10119.6 (3)
C6—C1—C2120.4 (3)C12—C11—H11A120.2
C6—C1—H1B119.8C10—C11—H11A120.2
C2—C1—H1B119.8C13—C12—C11120.4 (3)
C3—C2—C1120.2 (3)C13—C12—H12A119.8
C3—C2—H2B119.9C11—C12—H12A119.8
C1—C2—H2B119.9C12—C13—C14119.9 (3)
C4—C3—C2118.8 (3)C12—C13—H13A120.0
C4—C3—C7120.7 (3)C14—C13—H13A120.0
C2—C3—C7120.4 (3)C13—C14—C15121.1 (3)
C3—C4—C5120.6 (3)C13—C14—H14A119.4
C3—C4—H4A119.7C15—C14—H14A119.4
C5—C4—H4A119.7C14—C15—C10118.4 (2)
C6—C5—C4119.8 (3)C14—C15—C16121.7 (2)
C6—C5—H5A120.1C10—C15—C16119.8 (3)
C4—C5—H5A120.1C17—C16—C15112.7 (2)
C5—C6—C1120.2 (3)C17—C16—H16A109.1
C5—C6—H6A119.9C15—C16—H16A109.1
C1—C6—H6A119.9C17—C16—H16B109.1
N1—C7—N2114.3 (3)C15—C16—H16B109.1
N1—C7—C3122.3 (3)H16A—C16—H16B107.8
N2—C7—C3123.4 (3)O4—C17—O3122.9 (2)
N2—C8—O1113.8 (2)O4—C17—C16125.7 (3)
N2—C8—C9131.1 (3)O3—C17—C16111.4 (2)
O1—C8—C9115.0 (2)O3—C18—H18A109.5
O2—C9—C8112.3 (2)O3—C18—H18B109.5
O2—C9—H9A109.1H18A—C18—H18B109.5
C8—C9—H9A109.1O3—C18—H18C109.5
O2—C9—H9B109.2H18A—C18—H18C109.5
C8—C9—H9B109.1H18B—C18—H18C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11A···O4i0.932.473.319 (4)152
C18—H18A···O3ii0.962.553.272 (5)132
C9—H9A···Cg3i0.972.813.503 (4)129
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1.
 

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