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Crystals of the title compound, C15H10F3NO3, are stabilized by N—H...O and C—H...O inter­molecular hydrogen bonds and by weak C—H...π inter­actions. In the structure, paired C—H...O hydrogen bonds link the mol­ecules into R22(10) dimers. The hydrogen-bonded R22(10) dimers are linked by intermolecular N—H...O hydrogen bonds and generate R64(22) rings. The phthalide section of the mol­ecule is planar and the dihedral angle between the phthalide group and the benzene ring is 56.31 (17)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032089/at2084sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032089/at2084Isup2.hkl
Contains datablock I

CCDC reference: 620633

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.071
  • wR factor = 0.198
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C17
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.104 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.61 mm PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 4 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: 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-[3-(trifluoromethyl)anilino]isobenzofuran-1(3H)-one top
Crystal data top
C15H10F3NO2F(000) = 600
Mr = 293.24Dx = 1.454 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 17541 reflections
a = 13.4659 (9) Åθ = 2.5–27.9°
b = 8.1794 (7) ŵ = 0.13 mm1
c = 12.2649 (8) ÅT = 296 K
β = 97.400 (5)°Prism, colourless
V = 1339.64 (17) Å30.61 × 0.42 × 0.12 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
2629 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1933 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.104
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.9°
ω scansh = 1616
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1010
Tmin = 0.942, Tmax = 0.986l = 1515
14507 measured 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)] = 0.071H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.198 w = 1/[σ2(Fo2) + (0.0685P)2 + 1.3237P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2629 reflectionsΔρmax = 0.40 e Å3
195 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.011 (3)
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
C10.4651 (2)0.6847 (4)0.5535 (2)0.0536 (8)
C20.3799 (2)0.6302 (4)0.6071 (2)0.0505 (7)
C30.2793 (3)0.6569 (5)0.5783 (3)0.0669 (9)
H30.25580.71670.51580.080*
C40.2147 (3)0.5927 (5)0.6446 (4)0.0790 (11)
H40.14600.60710.62640.095*
C50.2509 (3)0.5062 (5)0.7386 (4)0.0767 (11)
H50.20570.46470.78290.092*
C60.3518 (3)0.4799 (4)0.7685 (3)0.0651 (9)
H60.37560.42270.83210.078*
C70.4164 (2)0.5426 (4)0.6996 (2)0.0485 (7)
C80.5282 (2)0.5295 (4)0.7071 (2)0.0501 (7)
H80.54700.41560.69610.060*
C90.6829 (2)0.5818 (4)0.8321 (3)0.0555 (8)
C100.7451 (2)0.5205 (4)0.7605 (3)0.0596 (8)
H100.71810.48140.69190.071*
C110.8480 (3)0.5174 (5)0.7913 (3)0.0661 (9)
C120.8895 (3)0.5753 (6)0.8923 (4)0.0853 (13)
H120.95850.57260.91260.102*
C130.8272 (3)0.6371 (6)0.9628 (3)0.0916 (14)
H130.85470.67791.03080.110*
C140.7248 (3)0.6396 (5)0.9344 (3)0.0758 (11)
H140.68370.67990.98360.091*
C170.9143 (3)0.4546 (6)0.7146 (4)0.0821 (12)
N10.5792 (2)0.5875 (4)0.8054 (2)0.0597 (8)
O10.4650 (2)0.7651 (3)0.47137 (19)0.0746 (8)
O20.55034 (16)0.6305 (3)0.61130 (17)0.0569 (6)
F11.0044 (2)0.4178 (6)0.7574 (3)0.1586 (17)
F20.9248 (3)0.5546 (5)0.6336 (4)0.1750 (19)
F30.8808 (2)0.3188 (5)0.6614 (3)0.1260 (12)
H10.550 (3)0.631 (5)0.853 (3)0.070 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0604 (19)0.0569 (18)0.0447 (16)0.0063 (14)0.0117 (14)0.0053 (15)
C20.0520 (17)0.0521 (17)0.0488 (16)0.0023 (13)0.0120 (13)0.0048 (14)
C30.059 (2)0.074 (2)0.067 (2)0.0043 (17)0.0049 (17)0.0022 (18)
C40.050 (2)0.089 (3)0.100 (3)0.0007 (18)0.015 (2)0.004 (2)
C50.060 (2)0.080 (3)0.096 (3)0.0032 (18)0.036 (2)0.008 (2)
C60.064 (2)0.065 (2)0.071 (2)0.0014 (16)0.0273 (17)0.0137 (17)
C70.0491 (16)0.0482 (16)0.0500 (16)0.0018 (13)0.0137 (13)0.0049 (14)
C80.0496 (17)0.0557 (17)0.0475 (16)0.0000 (13)0.0151 (13)0.0025 (14)
C90.0563 (18)0.0586 (19)0.0507 (17)0.0035 (14)0.0036 (14)0.0061 (15)
C100.0520 (18)0.068 (2)0.0585 (19)0.0015 (15)0.0054 (15)0.0040 (16)
C110.0523 (19)0.075 (2)0.070 (2)0.0001 (16)0.0033 (16)0.0184 (19)
C120.062 (2)0.114 (3)0.076 (3)0.009 (2)0.010 (2)0.018 (2)
C130.087 (3)0.123 (4)0.059 (2)0.011 (3)0.013 (2)0.001 (2)
C140.080 (3)0.093 (3)0.053 (2)0.003 (2)0.0040 (18)0.0002 (19)
C170.055 (2)0.101 (3)0.090 (3)0.006 (2)0.010 (2)0.013 (3)
N10.0534 (16)0.079 (2)0.0473 (15)0.0098 (14)0.0092 (12)0.0084 (14)
O10.0895 (19)0.0852 (18)0.0517 (13)0.0070 (14)0.0193 (12)0.0124 (13)
O20.0517 (12)0.0736 (15)0.0478 (11)0.0076 (10)0.0153 (9)0.0016 (11)
F10.0621 (16)0.253 (5)0.158 (3)0.044 (2)0.0021 (17)0.030 (3)
F20.210 (4)0.168 (3)0.176 (3)0.061 (3)0.134 (3)0.073 (3)
F30.0864 (19)0.157 (3)0.143 (3)0.0073 (19)0.0431 (18)0.043 (2)
Geometric parameters (Å, º) top
C1—O11.203 (4)C9—C101.384 (5)
C1—O21.344 (4)C9—C141.390 (5)
C1—C21.463 (4)C9—N11.393 (4)
C2—C31.372 (5)C10—C111.388 (5)
C2—C71.378 (4)C10—H100.9300
C3—C41.370 (5)C11—C121.376 (6)
C3—H30.9300C11—C171.471 (6)
C4—C51.387 (6)C12—C131.376 (6)
C4—H40.9300C12—H120.9300
C5—C61.378 (5)C13—C141.379 (6)
C5—H50.9300C13—H130.9300
C6—C71.387 (4)C14—H140.9300
C6—H60.9300C17—F11.295 (5)
C7—C81.500 (4)C17—F21.309 (5)
C8—N11.392 (4)C17—F31.337 (6)
C8—O21.497 (4)N1—H10.83 (4)
C8—H80.9800
O1—C1—O2122.0 (3)C10—C9—N1122.2 (3)
O1—C1—C2128.8 (3)C14—C9—N1118.7 (3)
O2—C1—C2109.2 (3)C9—C10—C11119.9 (3)
C3—C2—C7122.1 (3)C9—C10—H10120.0
C3—C2—C1129.9 (3)C11—C10—H10120.0
C7—C2—C1108.1 (3)C12—C11—C10120.9 (4)
C4—C3—C2117.9 (4)C12—C11—C17119.1 (4)
C4—C3—H3121.1C10—C11—C17120.0 (4)
C2—C3—H3121.1C13—C12—C11118.8 (4)
C3—C4—C5120.4 (3)C13—C12—H12120.6
C3—C4—H4119.8C11—C12—H12120.6
C5—C4—H4119.8C12—C13—C14121.1 (4)
C6—C5—C4122.0 (3)C12—C13—H13119.4
C6—C5—H5119.0C14—C13—H13119.4
C4—C5—H5119.0C13—C14—C9120.0 (4)
C5—C6—C7117.0 (3)C13—C14—H14120.0
C5—C6—H6121.5C9—C14—H14120.0
C7—C6—H6121.5F1—C17—F2105.4 (4)
C2—C7—C6120.6 (3)F1—C17—F3104.2 (4)
C2—C7—C8109.7 (3)F2—C17—F3102.2 (4)
C6—C7—C8129.8 (3)F1—C17—C11115.9 (4)
N1—C8—O2111.5 (3)F2—C17—C11113.7 (4)
N1—C8—C7114.1 (2)F3—C17—C11114.1 (4)
O2—C8—C7102.3 (2)C8—N1—C9124.1 (3)
N1—C8—H8109.6C8—N1—H1122 (3)
O2—C8—H8109.6C9—N1—H1113 (3)
C7—C8—H8109.6C1—O2—C8110.6 (2)
C10—C9—C14119.1 (3)
O1—C1—C2—C30.4 (6)C9—C10—C11—C17179.1 (4)
O2—C1—C2—C3179.6 (3)C10—C11—C12—C130.2 (6)
O1—C1—C2—C7179.4 (3)C17—C11—C12—C13178.6 (4)
O2—C1—C2—C70.5 (3)C11—C12—C13—C140.9 (7)
C7—C2—C3—C40.3 (5)C12—C13—C14—C91.2 (7)
C1—C2—C3—C4179.2 (3)C10—C9—C14—C130.8 (6)
C2—C3—C4—C51.1 (6)N1—C9—C14—C13179.3 (4)
C3—C4—C5—C60.7 (7)C12—C11—C17—F117.7 (6)
C4—C5—C6—C70.6 (6)C10—C11—C17—F1163.5 (4)
C3—C2—C7—C61.1 (5)C12—C11—C17—F2104.6 (5)
C1—C2—C7—C6178.1 (3)C10—C11—C17—F274.2 (6)
C3—C2—C7—C8178.1 (3)C12—C11—C17—F3138.8 (4)
C1—C2—C7—C82.8 (3)C10—C11—C17—F342.5 (5)
C5—C6—C7—C21.5 (5)O2—C8—N1—C967.3 (4)
C5—C6—C7—C8177.5 (3)C7—C8—N1—C9177.4 (3)
C2—C7—C8—N1124.2 (3)C10—C9—N1—C81.7 (5)
C6—C7—C8—N156.7 (5)C14—C9—N1—C8178.2 (3)
C2—C7—C8—O23.7 (3)O1—C1—O2—C8178.2 (3)
C6—C7—C8—O2177.2 (3)C2—C1—O2—C81.9 (3)
C14—C9—C10—C110.0 (5)N1—C8—O2—C1125.7 (3)
N1—C9—C10—C11179.9 (3)C7—C8—O2—C13.4 (3)
C9—C10—C11—C120.3 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.83 (4)2.14 (4)2.962 (4)176 (4)
C8—H8···O1ii0.982.523.264 (4)133
C8—H8···Cg1iii0.983.313.979 (4)128
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x+1, y+1, z+1; (iii) x+1, y+1/2, z+1/2.
 

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