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The crystal structure of the title compound, C15H13NO2, is stabilized by inversion-related N—H...O and C—H...O inter­molecular hydrogen bonds and also by C—H...π inter­actions. The N—H...O and C—H...O hydrogen bonds generate C(7) chains and R22(6) R44(20) R22(6) ring motifs. These motifs are linked to each other by C—H...π inter­actions, generating a three-dimensional network. The phthal­ide group is planar and makes a dihedral angle of 69.96 (2)° with the p-tolyl ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014080/at2247sup1.cif
Contains datablocks I, orhanm50

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014080/at2247Isup2.hkl
Contains datablock I

CCDC reference: 642901

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.039
  • wR factor = 0.103
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 15.04 Cell volume su given = 13.00 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.68 mm PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O2 .. 2.66 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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-methyanilino)isobenzofuran-1(3H)-one top
Crystal data top
C15H13NO2F(000) = 504
Mr = 239.26Dx = 1.314 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 18611 reflections
a = 13.2510 (9) Åθ = 2.6–28.0°
b = 6.8217 (3) ŵ = 0.09 mm1
c = 16.0257 (12) ÅT = 296 K
β = 123.391 (5)°Prism, colourless
V = 1209.51 (13) Å30.68 × 0.50 × 0.41 mm
Z = 4
Data collection top
STOE IPDS 2
diffractometer
2380 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1905 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.091
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.6°
ω scansh = 1616
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 88
Tmin = 0.946, Tmax = 0.972l = 1919
18611 measured reflections
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0476P)2 + 0.0922P]
where P = (Fo2 + 2Fc2)/3
2380 reflections(Δ/σ)max < 0.001
167 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.15 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*/UeqOcc. (<1)
C10.53371 (12)0.25761 (17)0.52760 (11)0.0567 (3)
C20.50631 (12)0.23118 (16)0.60387 (10)0.0537 (3)
C30.58285 (13)0.2042 (2)0.70599 (11)0.0655 (4)
H30.66620.19770.73670.079*
C40.53177 (15)0.1874 (2)0.76037 (11)0.0711 (4)
H40.58120.17200.82930.085*
C50.40803 (15)0.1931 (2)0.71420 (11)0.0684 (4)
H50.37550.18070.75260.082*
C60.33150 (13)0.21678 (19)0.61215 (11)0.0603 (3)
H60.24810.21870.58120.072*
C70.38262 (12)0.23745 (17)0.55765 (10)0.0523 (3)
C80.32392 (12)0.27281 (19)0.44823 (10)0.0545 (3)
H80.28350.40060.43080.065*
C90.15610 (11)0.15168 (19)0.28462 (9)0.0540 (3)
C100.08236 (12)0.0063 (2)0.23152 (10)0.0629 (4)
H100.09590.12700.26300.075*
C110.01047 (13)0.0136 (2)0.13296 (11)0.0691 (4)
H110.05880.09450.09920.083*
C120.03434 (13)0.1891 (2)0.08241 (10)0.0656 (4)
C130.04218 (13)0.3430 (2)0.13460 (11)0.0692 (4)
H130.02970.46230.10220.083*
C140.13715 (13)0.3263 (2)0.23379 (11)0.0646 (4)
H140.18820.43250.26630.077*
C150.14186 (15)0.2118 (3)0.02370 (12)0.0859 (5)
H15A0.18370.08890.04700.129*0.50
H15B0.11470.25150.06570.129*0.50
H15C0.19550.30940.02590.129*0.50
H15D0.14560.34430.04540.129*0.50
H15E0.21460.18170.02670.129*0.50
H15F0.13380.12380.06650.129*0.50
N10.24036 (10)0.12893 (18)0.38732 (8)0.0604 (3)
O10.63065 (9)0.25959 (14)0.53687 (9)0.0719 (3)
O20.42944 (9)0.28242 (14)0.43806 (7)0.0623 (3)
H10.2617 (14)0.009 (2)0.4090 (12)0.075 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0553 (8)0.0450 (6)0.0698 (9)0.0000 (5)0.0345 (7)0.0014 (5)
C20.0519 (7)0.0447 (6)0.0579 (7)0.0004 (5)0.0261 (6)0.0010 (5)
C30.0560 (8)0.0590 (8)0.0626 (8)0.0003 (6)0.0207 (7)0.0040 (6)
C40.0794 (10)0.0645 (8)0.0524 (8)0.0001 (7)0.0255 (7)0.0059 (6)
C50.0844 (10)0.0640 (8)0.0631 (9)0.0029 (7)0.0447 (8)0.0023 (6)
C60.0597 (8)0.0596 (8)0.0634 (8)0.0020 (6)0.0350 (7)0.0002 (6)
C70.0528 (7)0.0468 (6)0.0530 (7)0.0011 (5)0.0265 (6)0.0000 (5)
C80.0511 (7)0.0548 (7)0.0552 (7)0.0001 (5)0.0278 (6)0.0007 (5)
C90.0461 (6)0.0633 (8)0.0526 (7)0.0004 (5)0.0271 (6)0.0000 (5)
C100.0603 (8)0.0647 (8)0.0611 (8)0.0045 (6)0.0318 (7)0.0012 (6)
C110.0584 (8)0.0823 (10)0.0611 (8)0.0112 (7)0.0295 (7)0.0099 (7)
C120.0514 (7)0.0928 (10)0.0534 (7)0.0013 (7)0.0294 (6)0.0002 (7)
C130.0636 (8)0.0800 (10)0.0613 (9)0.0032 (7)0.0327 (7)0.0129 (7)
C140.0588 (8)0.0670 (8)0.0621 (8)0.0061 (6)0.0296 (7)0.0029 (6)
C150.0625 (9)0.1238 (15)0.0584 (9)0.0033 (9)0.0250 (8)0.0039 (9)
N10.0591 (6)0.0531 (7)0.0547 (6)0.0025 (5)0.0223 (5)0.0016 (5)
O10.0621 (6)0.0623 (6)0.1010 (8)0.0023 (4)0.0510 (6)0.0060 (5)
O20.0608 (6)0.0694 (6)0.0602 (6)0.0014 (4)0.0355 (5)0.0022 (4)
Geometric parameters (Å, º) top
C1—O11.2093 (16)C9—C101.3873 (18)
C1—O21.3470 (17)C9—N11.3990 (17)
C1—C21.465 (2)C10—C111.374 (2)
C2—C71.3786 (19)C10—H100.9300
C2—C31.383 (2)C11—C121.381 (2)
C3—C41.371 (2)C11—H110.9300
C3—H30.9300C12—C131.377 (2)
C4—C51.379 (2)C12—C151.510 (2)
C4—H40.9300C13—C141.3862 (19)
C5—C61.380 (2)C13—H130.9300
C5—H50.9300C14—H140.9300
C6—C71.376 (2)C15—H15A0.9600
C6—H60.9300C15—H15B0.9600
C7—C81.4955 (19)C15—H15C0.9600
C8—N11.3973 (17)C15—H15D0.9600
C8—O21.4957 (17)C15—H15E0.9600
C8—H80.9800C15—H15F0.9600
C9—C141.3860 (19)N1—H10.870 (16)
O1—C1—O2121.80 (13)C12—C11—H11119.0
O1—C1—C2129.27 (13)C13—C12—C11116.76 (13)
O2—C1—C2108.93 (11)C13—C12—C15121.93 (15)
C7—C2—C3121.37 (13)C11—C12—C15121.28 (15)
C7—C2—C1108.37 (12)C12—C13—C14122.28 (14)
C3—C2—C1130.26 (13)C12—C13—H13118.9
C4—C3—C2117.78 (14)C14—C13—H13118.9
C4—C3—H3121.1C9—C14—C13120.07 (13)
C2—C3—H3121.1C9—C14—H14120.0
C3—C4—C5120.90 (14)C13—C14—H14120.0
C3—C4—H4119.5C12—C15—H15A109.5
C5—C4—H4119.5C12—C15—H15B109.5
C4—C5—C6121.37 (14)H15A—C15—H15B109.5
C4—C5—H5119.3C12—C15—H15C109.5
C6—C5—H5119.3H15A—C15—H15C109.5
C7—C6—C5117.84 (13)H15B—C15—H15C109.5
C7—C6—H6121.1C12—C15—H15D109.5
C5—C6—H6121.1H15A—C15—H15D141.1
C6—C7—C2120.72 (13)H15B—C15—H15D56.3
C6—C7—C8129.85 (12)H15C—C15—H15D56.3
C2—C7—C8109.41 (12)C12—C15—H15E109.5
N1—C8—C7113.99 (11)H15A—C15—H15E56.3
N1—C8—O2112.56 (11)H15B—C15—H15E141.1
C7—C8—O2102.75 (10)H15C—C15—H15E56.3
N1—C8—H8109.1H15D—C15—H15E109.5
C7—C8—H8109.1C12—C15—H15F109.5
O2—C8—H8109.1H15A—C15—H15F56.3
C14—C9—C10117.94 (13)H15B—C15—H15F56.3
C14—C9—N1123.78 (12)H15C—C15—H15F141.1
C10—C9—N1118.17 (12)H15D—C15—H15F109.5
C11—C10—C9120.75 (13)H15E—C15—H15F109.5
C11—C10—H10119.6C8—N1—C9123.81 (12)
C9—C10—H10119.6C8—N1—H1114.9 (10)
C10—C11—C12122.07 (14)C9—N1—H1116.6 (10)
C10—C11—H11119.0C1—O2—C8110.53 (10)
O1—C1—C2—C7179.27 (13)C14—C9—C10—C113.3 (2)
O2—C1—C2—C70.99 (13)N1—C9—C10—C11173.03 (13)
O1—C1—C2—C30.9 (2)C9—C10—C11—C120.3 (2)
O2—C1—C2—C3178.81 (12)C10—C11—C12—C132.1 (2)
C7—C2—C3—C41.19 (19)C10—C11—C12—C15175.77 (14)
C1—C2—C3—C4178.59 (13)C11—C12—C13—C141.5 (2)
C2—C3—C4—C51.4 (2)C15—C12—C13—C14176.36 (15)
C3—C4—C5—C60.3 (2)C10—C9—C14—C133.9 (2)
C4—C5—C6—C70.9 (2)N1—C9—C14—C13172.24 (13)
C5—C6—C7—C21.09 (19)C12—C13—C14—C91.5 (2)
C5—C6—C7—C8177.32 (13)C7—C8—N1—C9165.36 (12)
C3—C2—C7—C60.04 (19)O2—C8—N1—C978.12 (15)
C1—C2—C7—C6179.87 (11)C14—C9—N1—C87.3 (2)
C3—C2—C7—C8178.66 (11)C10—C9—N1—C8176.59 (12)
C1—C2—C7—C81.17 (14)O1—C1—O2—C8179.84 (11)
C6—C7—C8—N158.47 (18)C2—C1—O2—C80.40 (13)
C2—C7—C8—N1122.98 (12)N1—C8—O2—C1123.33 (12)
C6—C7—C8—O2179.44 (12)C7—C8—O2—C10.28 (12)
C2—C7—C8—O20.90 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.870 (16)2.189 (17)3.0226 (16)160.2 (15)
C5—H5···O2ii0.932.663.4436 (18)143
C8—H8···O1iii0.982.513.2306 (16)131
C10—H10···Cg1iv0.933.013.466127
Symmetry codes: (i) x+1, y, z+1; (ii) x, y+1/2, z+1/2; (iii) x+1, y+1, z+1; (iv) x, y1/2, z+1/2.
 

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