The title molecule, C
15H
11NO
2, 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
CCDC reference: 604990
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.039
- wR factor = 0.099
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
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
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
C15H11NO2 | F(000) = 496 |
Mr = 237.25 | Dx = 1.364 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 20339 reflections |
a = 7.610 (3) Å | θ = 2.4–28.0° |
b = 11.311 (2) Å | µ = 0.09 mm−1 |
c = 13.422 (4) Å | T = 296 K |
β = 90.16 (3)° | Prism, red |
V = 1155.3 (6) Å3 | 0.62 × 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 focus | 1948 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.025 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.4° |
ω scans | h = −9→9 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −13→13 |
Tmin = 0.946, Tmax = 0.957 | l = −16→16 |
7903 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-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 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.99258 (16) | 0.80917 (10) | 0.49166 (9) | 0.0630 (4) | |
O2 | 1.00809 (15) | 0.77863 (9) | 0.27473 (8) | 0.0574 (4) | |
N1 | 0.85474 (14) | 0.60874 (9) | 0.31148 (8) | 0.0382 (3) | |
C1 | 0.79988 (16) | 0.55149 (11) | 0.39962 (9) | 0.0372 (4) | |
C2 | 0.72043 (19) | 0.44293 (12) | 0.40842 (11) | 0.0462 (4) | |
C3 | 0.6816 (2) | 0.40447 (15) | 0.50403 (12) | 0.0562 (5) | |
C4 | 0.7220 (2) | 0.47116 (17) | 0.58745 (12) | 0.0609 (6) | |
C5 | 0.8034 (2) | 0.57947 (15) | 0.57800 (11) | 0.0537 (5) | |
C6 | 0.84156 (17) | 0.61970 (12) | 0.48338 (10) | 0.0422 (4) | |
C7 | 0.93218 (18) | 0.72526 (12) | 0.44796 (10) | 0.0445 (4) | |
C8 | 0.93995 (17) | 0.71130 (11) | 0.33296 (10) | 0.0408 (4) | |
C9 | 0.83982 (17) | 0.55884 (12) | 0.21150 (9) | 0.0402 (4) | |
C10 | 0.65165 (17) | 0.54140 (11) | 0.17844 (9) | 0.0375 (4) | |
C11 | 0.5993 (2) | 0.43256 (13) | 0.14219 (11) | 0.0495 (4) | |
C12 | 0.4291 (2) | 0.41495 (15) | 0.10880 (13) | 0.0578 (5) | |
C13 | 0.30935 (19) | 0.50579 (15) | 0.11106 (11) | 0.0535 (5) | |
C14 | 0.3596 (2) | 0.61425 (14) | 0.14728 (12) | 0.0514 (5) | |
C15 | 0.53005 (19) | 0.63223 (12) | 0.18076 (10) | 0.0454 (4) | |
H2 | 0.69390 | 0.39720 | 0.35280 | 0.0560* | |
H3 | 0.62670 | 0.33170 | 0.51230 | 0.0670* | |
H4 | 0.69400 | 0.44270 | 0.65040 | 0.0730* | |
H5 | 0.83180 | 0.62420 | 0.63390 | 0.0640* | |
H9A | 0.89990 | 0.48320 | 0.20990 | 0.0480* | |
H9B | 0.89820 | 0.61100 | 0.16470 | 0.0480* | |
H11 | 0.67930 | 0.37050 | 0.14020 | 0.0590* | |
H12 | 0.39560 | 0.34120 | 0.08470 | 0.0690* | |
H13 | 0.19520 | 0.49390 | 0.08820 | 0.0640* | |
H14 | 0.27880 | 0.67590 | 0.14940 | 0.0620* | |
H15 | 0.56290 | 0.70600 | 0.20500 | 0.0540* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0698 (7) | 0.0507 (6) | 0.0684 (7) | −0.0016 (5) | −0.0213 (6) | −0.0165 (5) |
O2 | 0.0663 (7) | 0.0446 (6) | 0.0613 (7) | −0.0165 (5) | −0.0052 (5) | 0.0085 (5) |
N1 | 0.0422 (6) | 0.0356 (5) | 0.0369 (5) | −0.0043 (4) | −0.0058 (4) | 0.0021 (4) |
C1 | 0.0329 (6) | 0.0397 (7) | 0.0390 (6) | 0.0028 (5) | −0.0039 (5) | 0.0041 (5) |
C2 | 0.0444 (7) | 0.0440 (7) | 0.0503 (8) | −0.0045 (6) | −0.0047 (6) | 0.0074 (6) |
C3 | 0.0453 (8) | 0.0602 (9) | 0.0632 (10) | −0.0027 (7) | 0.0004 (7) | 0.0214 (8) |
C4 | 0.0505 (9) | 0.0857 (12) | 0.0466 (8) | 0.0090 (8) | 0.0052 (7) | 0.0208 (8) |
C5 | 0.0487 (8) | 0.0722 (10) | 0.0403 (7) | 0.0128 (7) | −0.0033 (6) | −0.0008 (7) |
C6 | 0.0378 (7) | 0.0473 (7) | 0.0413 (7) | 0.0072 (6) | −0.0063 (5) | −0.0016 (6) |
C7 | 0.0415 (7) | 0.0415 (7) | 0.0503 (8) | 0.0062 (6) | −0.0134 (6) | −0.0066 (6) |
C8 | 0.0391 (7) | 0.0340 (6) | 0.0491 (7) | −0.0005 (5) | −0.0085 (5) | 0.0016 (5) |
C9 | 0.0413 (7) | 0.0410 (7) | 0.0384 (7) | 0.0001 (6) | −0.0006 (5) | −0.0028 (5) |
C10 | 0.0417 (7) | 0.0407 (7) | 0.0300 (6) | −0.0013 (5) | −0.0008 (5) | 0.0013 (5) |
C11 | 0.0485 (8) | 0.0435 (7) | 0.0565 (8) | 0.0026 (6) | −0.0043 (6) | −0.0095 (6) |
C12 | 0.0520 (9) | 0.0548 (9) | 0.0664 (10) | −0.0071 (7) | −0.0062 (7) | −0.0159 (7) |
C13 | 0.0410 (7) | 0.0688 (10) | 0.0507 (8) | −0.0040 (7) | −0.0056 (6) | −0.0003 (7) |
C14 | 0.0460 (8) | 0.0547 (8) | 0.0535 (8) | 0.0101 (7) | −0.0017 (6) | 0.0050 (7) |
C15 | 0.0498 (8) | 0.0391 (7) | 0.0472 (7) | 0.0015 (6) | −0.0020 (6) | −0.0005 (6) |
Geometric parameters (Å, º) top
O1—C7 | 1.2061 (18) | C11—C12 | 1.384 (2) |
O2—C8 | 1.2091 (17) | C12—C13 | 1.374 (2) |
N1—C1 | 1.4128 (17) | C13—C14 | 1.374 (2) |
N1—C8 | 1.3595 (17) | C14—C15 | 1.387 (2) |
N1—C9 | 1.4599 (17) | C2—H2 | 0.9300 |
C1—C2 | 1.3739 (19) | C3—H3 | 0.9300 |
C1—C6 | 1.3992 (19) | C4—H4 | 0.9300 |
C2—C3 | 1.388 (2) | C5—H5 | 0.9300 |
C3—C4 | 1.384 (2) | C9—H9A | 0.9700 |
C4—C5 | 1.379 (3) | C9—H9B | 0.9700 |
C5—C6 | 1.381 (2) | C11—H11 | 0.9300 |
C6—C7 | 1.459 (2) | C12—H12 | 0.9300 |
C7—C8 | 1.553 (2) | C13—H13 | 0.9300 |
C9—C10 | 1.5109 (19) | C14—H14 | 0.9300 |
C10—C11 | 1.382 (2) | C15—H15 | 0.9300 |
C10—C15 | 1.383 (2) | | |
| | | |
O1···O2 | 2.935 (2) | C12···C7x | 3.568 (3) |
O2···O1 | 2.935 (2) | C13···C11ix | 3.541 (3) |
O2···C9i | 3.379 (2) | C2···H9A | 3.0300 |
O1···H13ii | 2.7500 | C7···H12ii | 2.8500 |
O1···H9Biii | 2.6000 | C9···H2 | 2.8600 |
O2···H9B | 2.5400 | C10···H2 | 2.8700 |
O2···H14iv | 2.9100 | C11···H2 | 2.9400 |
O2···H9Ai | 2.4300 | C14···H4vii | 2.8200 |
O2···H11i | 2.8300 | C15···H4vii | 2.9600 |
O2···H5v | 2.5600 | H2···C9 | 2.8600 |
N1···H15 | 2.8600 | H2···C10 | 2.8700 |
C1···C5vi | 3.376 (2) | H2···C11 | 2.9400 |
C2···C10 | 3.322 (2) | H2···H14x | 2.5100 |
C2···C4vii | 3.505 (3) | H4···C14vii | 2.8200 |
C3···C4vii | 3.592 (3) | H4···C15vii | 2.9600 |
C3···C3vii | 3.510 (3) | H5···O2iii | 2.5600 |
C3···C7vi | 3.346 (2) | H9A···C2 | 3.0300 |
C4···C7vi | 3.478 (3) | H9A···H11 | 2.3000 |
C4···C2vii | 3.505 (3) | H9A···O2viii | 2.4300 |
C4···C3vii | 3.592 (3) | H9B···O2 | 2.5400 |
C4···C8vi | 3.465 (3) | H9B···O1v | 2.6000 |
C5···C1vi | 3.376 (2) | H11···H9A | 2.3000 |
C7···C12ii | 3.568 (3) | H11···O2viii | 2.8300 |
C7···C4vi | 3.478 (3) | H12···C7x | 2.8500 |
C7···C3vi | 3.346 (2) | H13···O1x | 2.7500 |
C8···C4vi | 3.465 (3) | H14···O2xi | 2.9100 |
C9···O2viii | 3.379 (2) | H14···H2ii | 2.5100 |
C10···C2 | 3.322 (2) | H15···N1 | 2.8600 |
C11···C13ix | 3.541 (3) | | |
| | | |
C1—N1—C8 | 110.82 (11) | C13—C14—C15 | 120.33 (14) |
C1—N1—C9 | 124.76 (11) | C10—C15—C14 | 120.61 (13) |
C8—N1—C9 | 124.10 (11) | C1—C2—H2 | 122.00 |
N1—C1—C2 | 127.79 (12) | C3—C2—H2 | 121.00 |
N1—C1—C6 | 110.68 (11) | C2—C3—H3 | 119.00 |
C2—C1—C6 | 121.50 (12) | C4—C3—H3 | 119.00 |
C1—C2—C3 | 117.04 (14) | C3—C4—H4 | 120.00 |
C2—C3—C4 | 122.00 (15) | C5—C4—H4 | 120.00 |
C3—C4—C5 | 120.58 (15) | C4—C5—H5 | 121.00 |
C4—C5—C6 | 118.24 (14) | C6—C5—H5 | 121.00 |
C1—C6—C5 | 120.63 (13) | N1—C9—H9A | 109.00 |
C1—C6—C7 | 107.20 (12) | N1—C9—H9B | 109.00 |
C5—C6—C7 | 132.08 (13) | C10—C9—H9A | 109.00 |
O1—C7—C6 | 131.71 (14) | C10—C9—H9B | 109.00 |
O1—C7—C8 | 123.22 (13) | H9A—C9—H9B | 108.00 |
C6—C7—C8 | 105.07 (11) | C10—C11—H11 | 120.00 |
O2—C8—N1 | 127.27 (13) | C12—C11—H11 | 120.00 |
O2—C8—C7 | 126.59 (12) | C11—C12—H12 | 120.00 |
N1—C8—C7 | 106.15 (11) | C13—C12—H12 | 120.00 |
N1—C9—C10 | 113.06 (11) | C12—C13—H13 | 120.00 |
C9—C10—C11 | 119.46 (12) | C14—C13—H13 | 120.00 |
C9—C10—C15 | 122.01 (12) | C13—C14—H14 | 120.00 |
C11—C10—C15 | 118.52 (13) | C15—C14—H14 | 120.00 |
C10—C11—C12 | 120.72 (14) | C10—C15—H15 | 120.00 |
C11—C12—C13 | 120.37 (15) | C14—C15—H15 | 120.00 |
C12—C13—C14 | 119.46 (14) | | |
| | | |
C8—N1—C1—C2 | −175.45 (13) | C4—C5—C6—C7 | −176.76 (15) |
C9—N1—C1—C2 | −1.8 (2) | C1—C6—C7—O1 | 179.89 (16) |
C8—N1—C1—C6 | 2.87 (15) | C5—C6—C7—C8 | 176.36 (15) |
C9—N1—C1—C6 | 176.54 (12) | C1—C6—C7—C8 | −0.21 (14) |
C9—N1—C8—C7 | −176.56 (11) | C5—C6—C7—O1 | −3.6 (3) |
C1—N1—C9—C10 | 65.02 (16) | C6—C7—C8—N1 | 1.87 (14) |
C8—N1—C9—C10 | −122.13 (13) | O1—C7—C8—O2 | 1.7 (2) |
C1—N1—C8—C7 | −2.85 (14) | O1—C7—C8—N1 | −178.22 (14) |
C1—N1—C8—O2 | 177.27 (14) | C6—C7—C8—O2 | −178.25 (14) |
C9—N1—C8—O2 | 3.6 (2) | N1—C9—C10—C11 | −128.34 (13) |
N1—C1—C6—C7 | −1.50 (15) | N1—C9—C10—C15 | 53.41 (16) |
N1—C1—C2—C3 | 178.84 (13) | C9—C10—C11—C12 | −178.20 (14) |
C6—C1—C2—C3 | 0.7 (2) | C15—C10—C11—C12 | 0.1 (2) |
N1—C1—C6—C5 | −178.54 (13) | C9—C10—C15—C14 | 178.18 (13) |
C2—C1—C6—C7 | 176.94 (13) | C11—C10—C15—C14 | −0.1 (2) |
C2—C1—C6—C5 | −0.1 (2) | C10—C11—C12—C13 | 0.1 (2) |
C1—C2—C3—C4 | −0.6 (2) | C11—C12—C13—C14 | −0.4 (2) |
C2—C3—C4—C5 | 0.0 (2) | C12—C13—C14—C15 | 0.4 (2) |
C3—C4—C5—C6 | 0.6 (2) | C13—C14—C15—C10 | −0.2 (2) |
C4—C5—C6—C1 | −0.6 (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, z−1/2; (vi) −x+2, −y+1, −z+1; (vii) −x+1, −y+1, −z+1; (viii) −x+2, y−1/2, −z+1/2; (ix) −x+1, −y+1, −z; (x) −x+1, y−1/2, −z+1/2; (xi) x−1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O2iii | 0.93 | 2.56 | 3.457 (2) | 162 |
C9—H9A···O2viii | 0.97 | 2.43 | 3.379 (2) | 167 |
C9—H9B···O2 | 0.97 | 2.54 | 2.921 (2) | 103 |
C9—H9B···O1v | 0.97 | 2.60 | 3.508 (2) | 157 |
Symmetry codes: (iii) x, −y+3/2, z+1/2; (v) x, −y+3/2, z−1/2; (viii) −x+2, y−1/2, −z+1/2. |