Download citation
Download citation
link to html
In the mol­ecule of the title compound, C16H13NO2, the N and C atoms of the phthalic anhydride and aniline units form a distorted trigonal–planar structure. The mol­ecules are linked by inter­molecular C—H...O hydrogen bonds, forming infinite chains along the [101] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019659/hk2044sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019659/hk2044Isup2.hkl
Contains datablock I

CCDC reference: 270376

Key indicators

  • Single-crystal X-ray study
  • T = 233 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.038
  • wR factor = 0.099
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

2-(2,4-Dimethylphenyl)-1H-isoindole-1,3(2H)-dione top
Crystal data top
C16H13NO2F(000) = 528
Mr = 251.27Dx = 1.298 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6329 reflections
a = 11.3169 (4) Åθ = 1.0–25.0°
b = 8.4281 (2) ŵ = 0.09 mm1
c = 13.5482 (5) ÅT = 233 K
β = 95.757 (2)°Prism, colorless
V = 1285.71 (7) Å30.4 × 0.3 × 0.2 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
1986 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
φ and ω scansh = 013
6524 measured reflectionsk = 910
2219 independent reflectionsl = 1616
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)] = 0.038H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0478P)2 + 0.3326P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.006
2219 reflectionsΔρmax = 0.19 e Å3
176 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.060 (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
O10.03531 (11)0.03032 (13)0.22056 (8)0.0580 (3)
O20.10899 (9)0.33815 (12)0.44916 (7)0.0501 (3)
N10.06001 (10)0.12677 (13)0.34393 (8)0.0361 (3)
C10.02091 (12)0.09706 (17)0.26020 (10)0.0388 (3)
C20.05311 (11)0.28370 (16)0.37628 (10)0.0371 (3)
C30.03548 (11)0.36233 (16)0.30358 (10)0.0369 (3)
C40.07120 (13)0.51873 (18)0.29673 (11)0.0475 (4)
H40.04190.59440.34400.057*
C50.15243 (14)0.55964 (19)0.21689 (12)0.0525 (4)
H50.17700.66580.20900.063*
C60.19759 (13)0.4479 (2)0.14906 (11)0.0512 (4)
H60.25350.47900.09660.061*
C70.16218 (13)0.29051 (19)0.15661 (10)0.0463 (4)
H70.19310.21410.11050.056*
C80.07950 (11)0.25075 (16)0.23472 (9)0.0371 (3)
C90.14389 (11)0.01056 (15)0.38407 (9)0.0347 (3)
C100.26448 (12)0.03124 (17)0.37479 (9)0.0391 (3)
C110.34040 (12)0.09006 (18)0.41060 (10)0.0444 (4)
H110.42230.07780.40660.053*
C120.30073 (14)0.22792 (18)0.45183 (10)0.0447 (4)
C130.17984 (14)0.24392 (16)0.45985 (10)0.0444 (4)
H130.15100.33620.48810.053*
C140.10204 (12)0.12514 (16)0.42657 (10)0.0393 (3)
H140.02050.13630.43270.047*
C1010.31201 (14)0.1768 (2)0.32756 (13)0.0589 (5)
H10A0.39480.16040.31760.088*
H10B0.30510.26760.37060.088*
H10C0.26670.19620.26410.088*
C1210.38583 (17)0.3587 (2)0.48665 (14)0.0674 (5)
H12A0.38060.44360.43800.101*
H12B0.36540.39940.54970.101*
H12C0.46620.31720.49460.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0740 (8)0.0436 (7)0.0521 (6)0.0054 (5)0.0146 (5)0.0116 (5)
O20.0560 (6)0.0432 (6)0.0483 (6)0.0030 (5)0.0094 (5)0.0094 (5)
N10.0394 (6)0.0315 (6)0.0361 (6)0.0051 (5)0.0030 (5)0.0017 (4)
C10.0423 (7)0.0391 (8)0.0344 (7)0.0006 (6)0.0005 (5)0.0018 (6)
C20.0376 (7)0.0350 (7)0.0385 (7)0.0018 (6)0.0034 (6)0.0019 (6)
C30.0355 (7)0.0370 (7)0.0389 (7)0.0035 (6)0.0073 (5)0.0027 (6)
C40.0494 (8)0.0388 (8)0.0549 (9)0.0083 (6)0.0081 (7)0.0013 (7)
C50.0495 (8)0.0489 (9)0.0608 (10)0.0165 (7)0.0139 (7)0.0157 (8)
C60.0419 (8)0.0643 (10)0.0476 (8)0.0128 (7)0.0059 (6)0.0201 (8)
C70.0420 (8)0.0574 (9)0.0387 (7)0.0021 (7)0.0004 (6)0.0066 (7)
C80.0348 (7)0.0417 (8)0.0353 (7)0.0023 (6)0.0052 (5)0.0044 (6)
C90.0402 (7)0.0323 (7)0.0308 (6)0.0054 (5)0.0005 (5)0.0016 (5)
C100.0419 (7)0.0425 (8)0.0333 (7)0.0047 (6)0.0050 (5)0.0009 (6)
C110.0410 (7)0.0542 (9)0.0383 (7)0.0117 (7)0.0046 (6)0.0004 (7)
C120.0566 (9)0.0441 (8)0.0325 (7)0.0167 (7)0.0011 (6)0.0014 (6)
C130.0620 (9)0.0332 (7)0.0377 (7)0.0028 (7)0.0031 (6)0.0008 (6)
C140.0427 (7)0.0353 (7)0.0394 (7)0.0002 (6)0.0020 (6)0.0029 (6)
C1010.0504 (9)0.0583 (10)0.0704 (11)0.0021 (8)0.0172 (8)0.0158 (9)
C1210.0779 (12)0.0642 (12)0.0588 (10)0.0335 (10)0.0005 (9)0.0107 (9)
Geometric parameters (Å, º) top
O1—C11.2041 (17)C9—C141.3851 (19)
O2—C21.2084 (16)C9—C101.3939 (19)
N1—C21.3979 (17)C10—C111.3911 (19)
N1—C11.4071 (17)C10—C1011.508 (2)
N1—C91.4326 (16)C11—C121.383 (2)
C1—C81.4801 (19)C11—H110.9400
C2—C31.4887 (18)C12—C131.390 (2)
C3—C41.379 (2)C12—C1211.508 (2)
C3—C81.3820 (19)C13—C141.379 (2)
C4—C51.391 (2)C13—H130.9400
C4—H40.9400C14—H140.9400
C5—C61.378 (2)C101—H10A0.9700
C5—H50.9400C101—H10B0.9700
C6—C71.386 (2)C101—H10C0.9700
C6—H60.9400C121—H12A0.9700
C7—C81.3817 (19)C121—H12B0.9700
C7—H70.9400C121—H12C0.9700
C2—N1—C1111.64 (11)C10—C9—N1119.85 (12)
C2—N1—C9125.70 (11)C11—C10—C9116.91 (13)
C1—N1—C9122.49 (11)C11—C10—C101120.79 (13)
O1—C1—N1124.49 (13)C9—C10—C101122.29 (12)
O1—C1—C8129.70 (13)C12—C11—C10122.95 (13)
N1—C1—C8105.81 (11)C12—C11—H11118.5
O2—C2—N1125.06 (12)C10—C11—H11118.5
O2—C2—C3129.34 (13)C11—C12—C13118.35 (13)
N1—C2—C3105.60 (11)C11—C12—C121121.15 (15)
C4—C3—C8121.43 (13)C13—C12—C121120.49 (15)
C4—C3—C2130.05 (13)C14—C13—C12120.35 (13)
C8—C3—C2108.48 (12)C14—C13—H13119.8
C3—C4—C5117.11 (15)C12—C13—H13119.8
C3—C4—H4121.4C13—C14—C9120.12 (13)
C5—C4—H4121.4C13—C14—H14119.9
C6—C5—C4121.42 (14)C9—C14—H14119.9
C6—C5—H5119.3C10—C101—H10A109.5
C4—C5—H5119.3C10—C101—H10B109.5
C5—C6—C7121.31 (14)H10A—C101—H10B109.5
C5—C6—H6119.3C10—C101—H10C109.5
C7—C6—H6119.3H10A—C101—H10C109.5
C8—C7—C6117.20 (14)H10B—C101—H10C109.5
C8—C7—H7121.4C12—C121—H12A109.5
C6—C7—H7121.4C12—C121—H12B109.5
C7—C8—C3121.51 (13)H12A—C121—H12B109.5
C7—C8—C1130.09 (13)C12—C121—H12C109.5
C3—C8—C1108.38 (11)H12A—C121—H12C109.5
C14—C9—C10121.29 (12)H12B—C121—H12C109.5
C14—C9—N1118.76 (12)
C2—N1—C1—O1177.12 (14)C2—C3—C8—C10.18 (15)
C9—N1—C1—O17.3 (2)O1—C1—C8—C73.1 (3)
C2—N1—C1—C83.01 (14)N1—C1—C8—C7176.74 (13)
C9—N1—C1—C8172.57 (11)O1—C1—C8—C3178.48 (15)
C1—N1—C2—O2176.50 (13)N1—C1—C8—C31.66 (15)
C9—N1—C2—O28.1 (2)C2—N1—C9—C14118.34 (14)
C1—N1—C2—C33.10 (14)C1—N1—C9—C1466.71 (17)
C9—N1—C2—C3172.31 (11)C2—N1—C9—C1065.29 (17)
O2—C2—C3—C44.6 (2)C1—N1—C9—C10109.66 (15)
N1—C2—C3—C4175.83 (14)C14—C9—C10—C110.34 (19)
O2—C2—C3—C8177.62 (14)N1—C9—C10—C11176.62 (11)
N1—C2—C3—C81.96 (14)C14—C9—C10—C101179.15 (14)
C8—C3—C4—C50.7 (2)N1—C9—C10—C1012.9 (2)
C2—C3—C4—C5176.83 (13)C9—C10—C11—C121.5 (2)
C3—C4—C5—C61.7 (2)C101—C10—C11—C12178.03 (14)
C4—C5—C6—C71.2 (2)C10—C11—C12—C131.6 (2)
C5—C6—C7—C80.2 (2)C10—C11—C12—C121177.96 (14)
C6—C7—C8—C31.2 (2)C11—C12—C13—C140.5 (2)
C6—C7—C8—C1177.03 (13)C121—C12—C13—C14179.01 (14)
C4—C3—C8—C70.7 (2)C12—C13—C14—C90.5 (2)
C2—C3—C8—C7178.74 (12)C10—C9—C14—C130.6 (2)
C4—C3—C8—C1177.84 (12)N1—C9—C14—C13175.68 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C121—H12B···O1i0.972.543.339 (2)140
Symmetry code: (i) x+1/2, y1/2, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds