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The title mol­ecule, C15H11NO2, is non-planar, the dihedral angle between the isatin group and the phenyl ring being 87.08 (5)°. The crystal structure is stabilized by C–H...O hydrogen bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010282/bt2037sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010282/bt2037Isup2.hkl
Contains datablock I

CCDC reference: 604990

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.039
  • wR factor = 0.099
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

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Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.62 mm PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C7 - C8 ... 1.55 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 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

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, 1997); 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).

N-Benzyl-indole-2,3-dione(N-benzylisatin) top
Crystal data top
C15H11NO2F(000) = 496
Mr = 237.25Dx = 1.364 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 20339 reflections
a = 7.610 (3) Åθ = 2.4–28.0°
b = 11.311 (2) ŵ = 0.09 mm1
c = 13.422 (4) ÅT = 296 K
β = 90.16 (3)°Prism, red
V = 1155.3 (6) Å30.62 × 0.56 × 0.49 mm
Z = 4
Data collection top
STOE IPDS 2
diffractometer
2266 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1948 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.025
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.4°
ω scansh = 99
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1313
Tmin = 0.946, Tmax = 0.957l = 1616
7903 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) = 0.099H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0485P)2 + 0.2006P]
where P = (Fo2 + 2Fc2)/3
2266 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = 0.20 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O10.99258 (16)0.80917 (10)0.49166 (9)0.0630 (4)
O21.00809 (15)0.77863 (9)0.27473 (8)0.0574 (4)
N10.85474 (14)0.60874 (9)0.31148 (8)0.0382 (3)
C10.79988 (16)0.55149 (11)0.39962 (9)0.0372 (4)
C20.72043 (19)0.44293 (12)0.40842 (11)0.0462 (4)
C30.6816 (2)0.40447 (15)0.50403 (12)0.0562 (5)
C40.7220 (2)0.47116 (17)0.58745 (12)0.0609 (6)
C50.8034 (2)0.57947 (15)0.57800 (11)0.0537 (5)
C60.84156 (17)0.61970 (12)0.48338 (10)0.0422 (4)
C70.93218 (18)0.72526 (12)0.44796 (10)0.0445 (4)
C80.93995 (17)0.71130 (11)0.33296 (10)0.0408 (4)
C90.83982 (17)0.55884 (12)0.21150 (9)0.0402 (4)
C100.65165 (17)0.54140 (11)0.17844 (9)0.0375 (4)
C110.5993 (2)0.43256 (13)0.14219 (11)0.0495 (4)
C120.4291 (2)0.41495 (15)0.10880 (13)0.0578 (5)
C130.30935 (19)0.50579 (15)0.11106 (11)0.0535 (5)
C140.3596 (2)0.61425 (14)0.14728 (12)0.0514 (5)
C150.53005 (19)0.63223 (12)0.18076 (10)0.0454 (4)
H20.693900.397200.352800.0560*
H30.626700.331700.512300.0670*
H40.694000.442700.650400.0730*
H50.831800.624200.633900.0640*
H9A0.899900.483200.209900.0480*
H9B0.898200.611000.164700.0480*
H110.679300.370500.140200.0590*
H120.395600.341200.084700.0690*
H130.195200.493900.088200.0640*
H140.278800.675900.149400.0620*
H150.562900.706000.205000.0540*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0698 (7)0.0507 (6)0.0684 (7)0.0016 (5)0.0213 (6)0.0165 (5)
O20.0663 (7)0.0446 (6)0.0613 (7)0.0165 (5)0.0052 (5)0.0085 (5)
N10.0422 (6)0.0356 (5)0.0369 (5)0.0043 (4)0.0058 (4)0.0021 (4)
C10.0329 (6)0.0397 (7)0.0390 (6)0.0028 (5)0.0039 (5)0.0041 (5)
C20.0444 (7)0.0440 (7)0.0503 (8)0.0045 (6)0.0047 (6)0.0074 (6)
C30.0453 (8)0.0602 (9)0.0632 (10)0.0027 (7)0.0004 (7)0.0214 (8)
C40.0505 (9)0.0857 (12)0.0466 (8)0.0090 (8)0.0052 (7)0.0208 (8)
C50.0487 (8)0.0722 (10)0.0403 (7)0.0128 (7)0.0033 (6)0.0008 (7)
C60.0378 (7)0.0473 (7)0.0413 (7)0.0072 (6)0.0063 (5)0.0016 (6)
C70.0415 (7)0.0415 (7)0.0503 (8)0.0062 (6)0.0134 (6)0.0066 (6)
C80.0391 (7)0.0340 (6)0.0491 (7)0.0005 (5)0.0085 (5)0.0016 (5)
C90.0413 (7)0.0410 (7)0.0384 (7)0.0001 (6)0.0006 (5)0.0028 (5)
C100.0417 (7)0.0407 (7)0.0300 (6)0.0013 (5)0.0008 (5)0.0013 (5)
C110.0485 (8)0.0435 (7)0.0565 (8)0.0026 (6)0.0043 (6)0.0095 (6)
C120.0520 (9)0.0548 (9)0.0664 (10)0.0071 (7)0.0062 (7)0.0159 (7)
C130.0410 (7)0.0688 (10)0.0507 (8)0.0040 (7)0.0056 (6)0.0003 (7)
C140.0460 (8)0.0547 (8)0.0535 (8)0.0101 (7)0.0017 (6)0.0050 (7)
C150.0498 (8)0.0391 (7)0.0472 (7)0.0015 (6)0.0020 (6)0.0005 (6)
Geometric parameters (Å, º) top
O1—C71.2061 (18)C11—C121.384 (2)
O2—C81.2091 (17)C12—C131.374 (2)
N1—C11.4128 (17)C13—C141.374 (2)
N1—C81.3595 (17)C14—C151.387 (2)
N1—C91.4599 (17)C2—H20.9300
C1—C21.3739 (19)C3—H30.9300
C1—C61.3992 (19)C4—H40.9300
C2—C31.388 (2)C5—H50.9300
C3—C41.384 (2)C9—H9A0.9700
C4—C51.379 (3)C9—H9B0.9700
C5—C61.381 (2)C11—H110.9300
C6—C71.459 (2)C12—H120.9300
C7—C81.553 (2)C13—H130.9300
C9—C101.5109 (19)C14—H140.9300
C10—C111.382 (2)C15—H150.9300
C10—C151.383 (2)
O1···O22.935 (2)C12···C7x3.568 (3)
O2···O12.935 (2)C13···C11ix3.541 (3)
O2···C9i3.379 (2)C2···H9A3.0300
O1···H13ii2.7500C7···H12ii2.8500
O1···H9Biii2.6000C9···H22.8600
O2···H9B2.5400C10···H22.8700
O2···H14iv2.9100C11···H22.9400
O2···H9Ai2.4300C14···H4vii2.8200
O2···H11i2.8300C15···H4vii2.9600
O2···H5v2.5600H2···C92.8600
N1···H152.8600H2···C102.8700
C1···C5vi3.376 (2)H2···C112.9400
C2···C103.322 (2)H2···H14x2.5100
C2···C4vii3.505 (3)H4···C14vii2.8200
C3···C4vii3.592 (3)H4···C15vii2.9600
C3···C3vii3.510 (3)H5···O2iii2.5600
C3···C7vi3.346 (2)H9A···C23.0300
C4···C7vi3.478 (3)H9A···H112.3000
C4···C2vii3.505 (3)H9A···O2viii2.4300
C4···C3vii3.592 (3)H9B···O22.5400
C4···C8vi3.465 (3)H9B···O1v2.6000
C5···C1vi3.376 (2)H11···H9A2.3000
C7···C12ii3.568 (3)H11···O2viii2.8300
C7···C4vi3.478 (3)H12···C7x2.8500
C7···C3vi3.346 (2)H13···O1x2.7500
C8···C4vi3.465 (3)H14···O2xi2.9100
C9···O2viii3.379 (2)H14···H2ii2.5100
C10···C23.322 (2)H15···N12.8600
C11···C13ix3.541 (3)
C1—N1—C8110.82 (11)C13—C14—C15120.33 (14)
C1—N1—C9124.76 (11)C10—C15—C14120.61 (13)
C8—N1—C9124.10 (11)C1—C2—H2122.00
N1—C1—C2127.79 (12)C3—C2—H2121.00
N1—C1—C6110.68 (11)C2—C3—H3119.00
C2—C1—C6121.50 (12)C4—C3—H3119.00
C1—C2—C3117.04 (14)C3—C4—H4120.00
C2—C3—C4122.00 (15)C5—C4—H4120.00
C3—C4—C5120.58 (15)C4—C5—H5121.00
C4—C5—C6118.24 (14)C6—C5—H5121.00
C1—C6—C5120.63 (13)N1—C9—H9A109.00
C1—C6—C7107.20 (12)N1—C9—H9B109.00
C5—C6—C7132.08 (13)C10—C9—H9A109.00
O1—C7—C6131.71 (14)C10—C9—H9B109.00
O1—C7—C8123.22 (13)H9A—C9—H9B108.00
C6—C7—C8105.07 (11)C10—C11—H11120.00
O2—C8—N1127.27 (13)C12—C11—H11120.00
O2—C8—C7126.59 (12)C11—C12—H12120.00
N1—C8—C7106.15 (11)C13—C12—H12120.00
N1—C9—C10113.06 (11)C12—C13—H13120.00
C9—C10—C11119.46 (12)C14—C13—H13120.00
C9—C10—C15122.01 (12)C13—C14—H14120.00
C11—C10—C15118.52 (13)C15—C14—H14120.00
C10—C11—C12120.72 (14)C10—C15—H15120.00
C11—C12—C13120.37 (15)C14—C15—H15120.00
C12—C13—C14119.46 (14)
C8—N1—C1—C2175.45 (13)C4—C5—C6—C7176.76 (15)
C9—N1—C1—C21.8 (2)C1—C6—C7—O1179.89 (16)
C8—N1—C1—C62.87 (15)C5—C6—C7—C8176.36 (15)
C9—N1—C1—C6176.54 (12)C1—C6—C7—C80.21 (14)
C9—N1—C8—C7176.56 (11)C5—C6—C7—O13.6 (3)
C1—N1—C9—C1065.02 (16)C6—C7—C8—N11.87 (14)
C8—N1—C9—C10122.13 (13)O1—C7—C8—O21.7 (2)
C1—N1—C8—C72.85 (14)O1—C7—C8—N1178.22 (14)
C1—N1—C8—O2177.27 (14)C6—C7—C8—O2178.25 (14)
C9—N1—C8—O23.6 (2)N1—C9—C10—C11128.34 (13)
N1—C1—C6—C71.50 (15)N1—C9—C10—C1553.41 (16)
N1—C1—C2—C3178.84 (13)C9—C10—C11—C12178.20 (14)
C6—C1—C2—C30.7 (2)C15—C10—C11—C120.1 (2)
N1—C1—C6—C5178.54 (13)C9—C10—C15—C14178.18 (13)
C2—C1—C6—C7176.94 (13)C11—C10—C15—C140.1 (2)
C2—C1—C6—C50.1 (2)C10—C11—C12—C130.1 (2)
C1—C2—C3—C40.6 (2)C11—C12—C13—C140.4 (2)
C2—C3—C4—C50.0 (2)C12—C13—C14—C150.4 (2)
C3—C4—C5—C60.6 (2)C13—C14—C15—C100.2 (2)
C4—C5—C6—C10.6 (2)
Symmetry codes: (i) x+2, y+1/2, z+1/2; (ii) x+1, y+1/2, z+1/2; (iii) x, y+3/2, z+1/2; (iv) x+1, y, z; (v) x, y+3/2, z1/2; (vi) x+2, y+1, z+1; (vii) x+1, y+1, z+1; (viii) x+2, y1/2, z+1/2; (ix) x+1, y+1, z; (x) x+1, y1/2, z+1/2; (xi) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O2iii0.932.563.457 (2)162
C9—H9A···O2viii0.972.433.379 (2)167
C9—H9B···O20.972.542.921 (2)103
C9—H9B···O1v0.972.603.508 (2)157
Symmetry codes: (iii) x, y+3/2, z+1/2; (v) x, y+3/2, z1/2; (viii) x+2, y1/2, z+1/2.
 

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