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The crystal structure of the title compound, C16H13NO3, is stabilized by an N—H...O and three C—H...O inter­molecular hydrogen bonds and by C—H... π inter­actions. The inter­molecular hydrogen bonds generate R44(33) and R44(29) ring motifs. These hydrogen-bonded rings are linked via C(3) chains, generating a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032570/sj2102sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032570/sj2102Isup2.hkl
Contains datablock I

CCDC reference: 621493

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.029
  • wR factor = 0.071
  • Data-to-parameter ratio = 7.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.95
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.99 From the CIF: _reflns_number_total 1300 Count of symmetry unique reflns 1300 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-(4-acetylanilino)isobenzofuran-1(3H)-one top
Crystal data top
C16H13NO3F(000) = 280
Mr = 267.27Dx = 1.391 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 7243 reflections
a = 4.0243 (5) Åθ = 2.3–28.0°
b = 14.3117 (12) ŵ = 0.10 mm1
c = 11.1107 (12) ÅT = 296 K
β = 94.002 (9)°Prism, colorless
V = 638.36 (12) Å30.23 × 0.19 × 0.14 mm
Z = 2
Data collection top
Stoe IPDS-2
diffractometer
1116 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focusRint = 0.051
Plane graphite monochromatorθmax = 26.0°, θmin = 2.3°
Detector resolution: 6.67 pixels mm-1h = 44
ω scansk = 1717
7243 measured reflectionsl = 1313
1300 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.071 w = 1/[σ2(Fo2) + (0.0394P)2 + 0.0165P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
1300 reflectionsΔρmax = 0.11 e Å3
187 parametersΔρmin = 0.12 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.040 (6)
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
C10.0661 (6)0.54006 (19)0.4995 (2)0.0516 (5)
C20.1653 (6)0.62294 (16)0.4347 (2)0.0457 (5)
C30.1251 (7)0.71654 (18)0.4620 (2)0.0582 (7)
H30.03000.73490.53220.070*
C40.2309 (8)0.78139 (17)0.3816 (3)0.0643 (7)
H40.20700.84480.39720.077*
C50.3722 (8)0.7531 (2)0.2781 (3)0.0646 (8)
H50.44180.79830.22510.078*
C60.4137 (7)0.65984 (16)0.2504 (2)0.0522 (6)
H60.50970.64150.18040.063*
C70.3061 (6)0.59522 (15)0.33125 (19)0.0435 (5)
C80.3188 (6)0.49058 (15)0.3279 (2)0.0440 (5)
H80.55140.46990.33640.053*
C90.2094 (6)0.35914 (14)0.1890 (2)0.0413 (5)
C100.0823 (6)0.32922 (16)0.07531 (19)0.0468 (5)
H100.03210.37100.02340.056*
C110.1254 (6)0.23883 (16)0.0400 (2)0.0478 (6)
H110.03890.21980.03590.057*
C120.2967 (6)0.17436 (15)0.1155 (2)0.0426 (5)
C130.4193 (6)0.20426 (16)0.2279 (2)0.0461 (5)
H130.53300.16220.27960.055*
C140.3771 (6)0.29514 (15)0.2653 (2)0.0468 (6)
H140.46100.31360.34180.056*
C150.3333 (6)0.07722 (15)0.0731 (2)0.0485 (6)
C160.5116 (8)0.00744 (17)0.1540 (3)0.0596 (7)
H16A0.55060.04840.10920.071*
H16B0.37800.00720.21970.071*
H16C0.72070.03310.18510.071*
N10.1603 (5)0.45111 (13)0.22315 (17)0.0475 (5)
O10.0702 (6)0.53323 (16)0.59211 (16)0.0756 (6)
O20.1488 (4)0.46302 (11)0.43641 (15)0.0518 (4)
O30.2175 (6)0.05329 (13)0.02658 (16)0.0686 (5)
H10.050 (9)0.486 (2)0.170 (3)0.076 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0551 (14)0.0572 (13)0.0422 (12)0.0021 (13)0.0010 (10)0.0032 (12)
C20.0470 (13)0.0465 (11)0.0430 (13)0.0010 (10)0.0017 (11)0.0052 (10)
C30.0625 (16)0.0551 (14)0.0560 (14)0.0071 (12)0.0024 (12)0.0156 (12)
C40.081 (2)0.0378 (13)0.0722 (18)0.0018 (12)0.0087 (15)0.0109 (12)
C50.080 (2)0.0466 (14)0.0665 (17)0.0073 (13)0.0028 (15)0.0073 (13)
C60.0604 (16)0.0487 (13)0.0475 (13)0.0029 (11)0.0047 (12)0.0006 (10)
C70.0451 (14)0.0413 (11)0.0437 (12)0.0020 (9)0.0006 (10)0.0025 (10)
C80.0483 (14)0.0425 (12)0.0411 (12)0.0005 (9)0.0016 (10)0.0017 (9)
C90.0476 (12)0.0371 (11)0.0391 (11)0.0018 (9)0.0030 (9)0.0006 (8)
C100.0564 (14)0.0446 (12)0.0383 (11)0.0014 (10)0.0038 (10)0.0031 (9)
C110.0566 (14)0.0466 (13)0.0393 (11)0.0065 (10)0.0034 (10)0.0036 (10)
C120.0464 (13)0.0409 (12)0.0408 (12)0.0046 (9)0.0054 (10)0.0024 (9)
C130.0549 (14)0.0404 (11)0.0424 (12)0.0010 (10)0.0001 (11)0.0024 (10)
C140.0576 (15)0.0436 (12)0.0382 (11)0.0001 (10)0.0032 (10)0.0018 (9)
C150.0584 (15)0.0419 (12)0.0459 (12)0.0096 (10)0.0087 (11)0.0031 (10)
C160.0733 (18)0.0431 (12)0.0628 (15)0.0061 (11)0.0086 (14)0.0036 (11)
N10.0586 (12)0.0386 (10)0.0439 (11)0.0036 (9)0.0056 (9)0.0031 (8)
O10.0955 (15)0.0832 (14)0.0504 (10)0.0078 (13)0.0225 (10)0.0032 (11)
O20.0644 (10)0.0469 (9)0.0440 (9)0.0037 (8)0.0026 (8)0.0010 (7)
O30.1013 (15)0.0505 (10)0.0525 (10)0.0134 (10)0.0052 (9)0.0096 (9)
Geometric parameters (Å, º) top
C1—O11.203 (3)C9—C141.390 (3)
C1—O21.360 (3)C9—C101.397 (3)
C1—C21.458 (4)C10—C111.366 (3)
C2—C71.375 (3)C10—H100.9300
C2—C31.386 (3)C11—C121.396 (3)
C3—C41.376 (4)C11—H110.9300
C3—H30.9300C12—C131.378 (3)
C4—C51.379 (4)C12—C151.479 (3)
C4—H40.9300C13—C141.380 (3)
C5—C61.383 (4)C13—H130.9300
C5—H50.9300C14—H140.9300
C6—C71.380 (3)C15—O31.220 (3)
C6—H60.9300C15—C161.493 (4)
C7—C81.499 (3)C16—H16A0.9600
C8—N11.406 (3)C16—H16B0.9600
C8—O21.481 (3)C16—H16C0.9600
C8—H80.9800N1—H10.87 (3)
C9—N11.388 (3)
O1—C1—O2121.2 (3)C14—C9—C10118.76 (19)
O1—C1—C2130.2 (2)C11—C10—C9120.3 (2)
O2—C1—C2108.63 (18)C11—C10—H10119.9
C7—C2—C3121.6 (2)C9—C10—H10119.9
C7—C2—C1108.7 (2)C10—C11—C12121.4 (2)
C3—C2—C1129.7 (2)C10—C11—H11119.3
C4—C3—C2117.6 (2)C12—C11—H11119.3
C4—C3—H3121.2C13—C12—C11118.01 (19)
C2—C3—H3121.2C13—C12—C15122.9 (2)
C3—C4—C5120.5 (2)C11—C12—C15119.0 (2)
C3—C4—H4119.7C12—C13—C14121.5 (2)
C5—C4—H4119.7C12—C13—H13119.3
C4—C5—C6122.2 (3)C14—C13—H13119.3
C4—C5—H5118.9C13—C14—C9120.1 (2)
C6—C5—H5118.9C13—C14—H14119.9
C7—C6—C5117.0 (2)C9—C14—H14119.9
C7—C6—H6121.5O3—C15—C12120.9 (2)
C5—C6—H6121.5O3—C15—C16119.7 (2)
C2—C7—C6121.1 (2)C12—C15—C16119.4 (2)
C2—C7—C8109.0 (2)C15—C16—H16A109.5
C6—C7—C8129.9 (2)C15—C16—H16B109.5
N1—C8—O2110.99 (18)H16A—C16—H16B109.5
N1—C8—C7114.1 (2)C15—C16—H16C109.5
O2—C8—C7103.16 (18)H16A—C16—H16C109.5
N1—C8—H8109.5H16B—C16—H16C109.5
O2—C8—H8109.5C9—N1—C8122.82 (19)
C7—C8—H8109.5C9—N1—H1116 (2)
N1—C9—C14122.06 (19)C8—N1—H1121 (2)
N1—C9—C10119.2 (2)C1—O2—C8110.32 (17)
O1—C1—C2—C7178.5 (3)C9—C10—C11—C120.2 (4)
O2—C1—C2—C70.5 (3)C10—C11—C12—C130.6 (3)
O1—C1—C2—C30.9 (4)C10—C11—C12—C15179.5 (3)
O2—C1—C2—C3178.2 (2)C11—C12—C13—C140.3 (3)
C7—C2—C3—C40.1 (4)C15—C12—C13—C14179.1 (2)
C1—C2—C3—C4177.3 (3)C12—C13—C14—C90.4 (4)
C2—C3—C4—C50.1 (4)N1—C9—C14—C13179.8 (2)
C3—C4—C5—C60.0 (5)C10—C9—C14—C130.8 (3)
C4—C5—C6—C70.2 (4)C13—C12—C15—O3179.1 (2)
C3—C2—C7—C60.1 (4)C11—C12—C15—O30.3 (3)
C1—C2—C7—C6178.0 (2)C13—C12—C15—C160.3 (4)
C3—C2—C7—C8179.4 (2)C11—C12—C15—C16179.1 (2)
C1—C2—C7—C82.8 (3)C14—C9—N1—C810.4 (3)
C5—C6—C7—C20.2 (4)C10—C9—N1—C8170.6 (2)
C5—C6—C7—C8179.3 (3)O2—C8—N1—C979.6 (3)
C2—C7—C8—N1124.2 (2)C7—C8—N1—C9164.4 (2)
C6—C7—C8—N156.6 (4)O1—C1—O2—C8178.9 (2)
C2—C7—C8—O23.7 (2)C2—C1—O2—C82.0 (2)
C6—C7—C8—O2177.1 (2)N1—C8—O2—C1126.0 (2)
N1—C9—C10—C11179.5 (2)C7—C8—O2—C13.5 (2)
C14—C9—C10—C110.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.87 (3)2.09 (3)2.959 (3)172 (3)
C6—H6···O3ii0.932.453.351 (3)164
C8—H8···O2iii0.982.583.493 (3)155
C16—H16B···O1iv0.962.573.457 (4)154
C8—H8···Cg1iii0.982.873.671 (3)140
Symmetry codes: (i) x, y+1/2, z; (ii) x+1, y+1/2, z; (iii) x+1, y, z; (iv) x, y1/2, z+1.
 

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