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organic compounds
In the structure of the title compound, C15H13N, the dihedral angle between the five- and the six-membered rings of the indole system is 1.19 (5)° and the phenyl ring makes a dihedral angle of 46.09 (5)° with the indole ring system.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012962/nc2030sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807012962/nc2030Isup2.hkl |
CCDC reference: 643063
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C)= 0.002 Å - R factor = 0.060
- wR factor = 0.157
- Data-to-parameter ratio = 18.3
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C)= 0.002 ÅcheckCIF/PLATON results
No syntax errors found No errors found in this datablock
Computing details top
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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).
1-Methyl-2-phenyl-1H-indole top
Crystal data top
| C15H13N | F(000) = 880 |
| Mr = 207.26 | Dx = 1.234 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 9521 reflections |
| a = 8.1957 (1) Å | θ = 2.4–30.5° |
| b = 15.8652 (3) Å | µ = 0.07 mm−1 |
| c = 17.1653 (3) Å | T = 294 K |
| V = 2231.94 (6) Å3 | Prism, colorless |
| Z = 8 | 0.35 × 0.20 × 0.15 mm |
Data collection top
| Rigaku R-AXIS RAPID-S diffractometer | 2146 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.080 |
| Graphite monochromator | θmax = 30.5°, θmin = 2.4° |
| ω scans | h = −11→11 |
| 60316 measured reflections | k = −22→20 |
| 3414 independent reflections | l = −24→24 |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.061 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.157 | w = 1/[σ2(Fo2) + (0.0597P)2 + 0.2662P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 3414 reflections | Δρmax = 0.14 e Å−3 |
| 187 parameters | Δρmin = −0.16 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0054 (11) |
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
| x | y | z | Uiso*/Ueq | ||
| N1 | 0.69104 (15) | −0.02624 (8) | 0.89841 (7) | 0.0567 (3) | |
| C1 | 0.53523 (18) | −0.00878 (10) | 0.87075 (8) | 0.0549 (4) | |
| C2 | 0.5352 (2) | 0.06949 (10) | 0.83742 (9) | 0.0609 (4) | |
| C3 | 0.69556 (19) | 0.10341 (10) | 0.84393 (8) | 0.0569 (4) | |
| C4 | 0.79057 (18) | 0.04153 (9) | 0.88152 (8) | 0.0555 (4) | |
| C5 | 0.9566 (2) | 0.05257 (12) | 0.89561 (10) | 0.0654 (4) | |
| C6 | 1.0257 (2) | 0.12777 (12) | 0.87299 (10) | 0.0686 (4) | |
| C7 | 0.9331 (2) | 0.19096 (12) | 0.83734 (10) | 0.0687 (5) | |
| C8 | 0.7701 (2) | 0.17938 (11) | 0.82203 (10) | 0.0660 (4) | |
| C9 | 0.39997 (18) | −0.06971 (10) | 0.87645 (9) | 0.0558 (4) | |
| C10 | 0.3649 (2) | −0.11392 (11) | 0.94430 (10) | 0.0640 (4) | |
| C11 | 0.2400 (2) | −0.17240 (12) | 0.94654 (12) | 0.0749 (5) | |
| C12 | 0.1473 (2) | −0.18728 (13) | 0.88119 (14) | 0.0817 (6) | |
| C13 | 0.1767 (2) | −0.14149 (13) | 0.81421 (13) | 0.0788 (5) | |
| C14 | 0.3015 (2) | −0.08343 (12) | 0.81145 (10) | 0.0661 (4) | |
| C15 | 0.7471 (2) | −0.10365 (11) | 0.93398 (13) | 0.0857 (6) | |
| H2 | 0.436 (2) | 0.0944 (11) | 0.8168 (11) | 0.078 (5)* | |
| H5 | 1.022 (2) | 0.0094 (12) | 0.9197 (11) | 0.084 (6)* | |
| H6 | 1.145 (3) | 0.1378 (11) | 0.8848 (10) | 0.080 (5)* | |
| H7 | 0.990 (2) | 0.2451 (13) | 0.8220 (11) | 0.093 (6)* | |
| H8 | 0.704 (2) | 0.2244 (11) | 0.7958 (10) | 0.084 (5)* | |
| H10 | 0.4287 (19) | −0.1048 (10) | 0.9903 (10) | 0.066 (5)* | |
| H11 | 0.221 (2) | −0.2038 (11) | 0.9944 (12) | 0.091 (6)* | |
| H12 | 0.056 (3) | −0.2288 (13) | 0.8838 (11) | 0.094 (6)* | |
| H13 | 0.110 (2) | −0.1520 (12) | 0.7689 (12) | 0.092 (6)* | |
| H14 | 0.325 (2) | −0.0523 (10) | 0.7642 (11) | 0.077 (5)* | |
| H15A | 0.8603 | −0.1120 | 0.9219 | 0.129* | |
| H15B | 0.6846 | −0.1501 | 0.9142 | 0.129* | |
| H15C | 0.7337 | −0.1002 | 0.9894 | 0.129* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0539 (7) | 0.0554 (7) | 0.0609 (7) | 0.0034 (6) | −0.0056 (5) | 0.0012 (5) |
| C1 | 0.0519 (8) | 0.0618 (9) | 0.0511 (7) | 0.0022 (7) | −0.0023 (6) | −0.0028 (6) |
| C2 | 0.0562 (9) | 0.0666 (10) | 0.0598 (9) | 0.0058 (7) | −0.0027 (7) | 0.0064 (7) |
| C3 | 0.0574 (8) | 0.0597 (9) | 0.0535 (8) | 0.0038 (7) | 0.0027 (6) | 0.0001 (6) |
| C4 | 0.0542 (8) | 0.0579 (8) | 0.0543 (8) | 0.0013 (7) | 0.0004 (6) | −0.0041 (6) |
| C5 | 0.0550 (9) | 0.0717 (11) | 0.0694 (10) | 0.0031 (8) | −0.0048 (7) | −0.0020 (8) |
| C6 | 0.0579 (10) | 0.0780 (12) | 0.0699 (10) | −0.0059 (9) | 0.0010 (8) | −0.0054 (8) |
| C7 | 0.0704 (11) | 0.0681 (11) | 0.0676 (10) | −0.0086 (8) | 0.0077 (8) | −0.0013 (8) |
| C8 | 0.0697 (11) | 0.0635 (10) | 0.0649 (10) | 0.0019 (8) | 0.0044 (8) | 0.0060 (8) |
| C9 | 0.0514 (8) | 0.0605 (9) | 0.0555 (8) | 0.0034 (7) | 0.0004 (6) | −0.0068 (6) |
| C10 | 0.0662 (10) | 0.0669 (10) | 0.0590 (9) | −0.0032 (8) | 0.0019 (7) | −0.0050 (7) |
| C11 | 0.0721 (11) | 0.0679 (11) | 0.0845 (13) | −0.0033 (9) | 0.0142 (9) | −0.0012 (9) |
| C12 | 0.0601 (11) | 0.0700 (12) | 0.1148 (17) | −0.0052 (9) | 0.0056 (10) | −0.0186 (11) |
| C13 | 0.0603 (10) | 0.0846 (13) | 0.0914 (14) | 0.0021 (9) | −0.0139 (9) | −0.0234 (11) |
| C14 | 0.0611 (9) | 0.0756 (11) | 0.0616 (10) | 0.0066 (8) | −0.0071 (7) | −0.0083 (8) |
| C15 | 0.0698 (11) | 0.0658 (11) | 0.1215 (17) | 0.0031 (9) | −0.0204 (11) | 0.0194 (10) |
Geometric parameters (Å, º) top
| N1—C4 | 1.3804 (19) | C9—C10 | 1.390 (2) |
| N1—C1 | 1.3904 (19) | C9—C14 | 1.394 (2) |
| N1—C15 | 1.446 (2) | C9—C1 | 1.474 (2) |
| C1—C2 | 1.367 (2) | C10—C11 | 1.382 (2) |
| C2—H2 | 0.969 (18) | C10—H10 | 0.959 (17) |
| C3—C8 | 1.403 (2) | C11—H11 | 0.973 (19) |
| C3—C4 | 1.409 (2) | C12—C11 | 1.375 (3) |
| C3—C2 | 1.424 (2) | C12—H12 | 0.99 (2) |
| C4—C5 | 1.393 (2) | C13—C12 | 1.381 (3) |
| C5—C6 | 1.377 (2) | C13—H13 | 0.96 (2) |
| C5—H5 | 0.962 (19) | C14—C13 | 1.377 (3) |
| C6—C7 | 1.398 (3) | C14—H14 | 0.969 (17) |
| C6—H6 | 1.01 (2) | C15—H15A | 0.9600 |
| C7—H7 | 1.01 (2) | C15—H15B | 0.9600 |
| C8—C7 | 1.374 (3) | C15—H15C | 0.9600 |
| C8—H8 | 1.004 (18) | ||
| C4—N1—C1 | 108.42 (12) | C3—C8—H8 | 119.7 (10) |
| C4—N1—C15 | 124.21 (14) | C10—C9—C14 | 118.18 (16) |
| C1—N1—C15 | 127.24 (14) | C10—C9—C1 | 122.83 (14) |
| C2—C1—N1 | 108.89 (14) | C14—C9—C1 | 118.99 (14) |
| C2—C1—C9 | 128.57 (14) | C11—C10—C9 | 121.02 (17) |
| N1—C1—C9 | 122.51 (14) | C11—C10—H10 | 118.9 (10) |
| C1—C2—C3 | 108.08 (14) | C9—C10—H10 | 120.1 (10) |
| C1—C2—H2 | 121.5 (11) | C12—C11—C10 | 120.1 (2) |
| C3—C2—H2 | 130.3 (11) | C12—C11—H11 | 120.6 (12) |
| C8—C3—C4 | 118.71 (15) | C10—C11—H11 | 119.2 (12) |
| C8—C3—C2 | 134.88 (15) | C11—C12—C13 | 119.50 (19) |
| C4—C3—C2 | 106.41 (14) | C11—C12—H12 | 119.3 (12) |
| N1—C4—C5 | 129.70 (15) | C13—C12—H12 | 121.1 (11) |
| N1—C4—C3 | 108.19 (14) | C14—C13—C12 | 120.65 (19) |
| C5—C4—C3 | 122.11 (15) | C14—C13—H13 | 120.6 (12) |
| C6—C5—C4 | 117.52 (17) | C12—C13—H13 | 118.8 (12) |
| C6—C5—H5 | 120.6 (11) | C13—C14—C9 | 120.45 (18) |
| C4—C5—H5 | 121.9 (11) | C13—C14—H14 | 121.0 (10) |
| C5—C6—C7 | 121.44 (17) | C9—C14—H14 | 118.5 (10) |
| C5—C6—H6 | 118.6 (10) | N1—C15—H15A | 109.5 |
| C7—C6—H6 | 120.0 (10) | N1—C15—H15B | 109.5 |
| C8—C7—C6 | 121.03 (17) | H15A—C15—H15B | 109.5 |
| C8—C7—H7 | 120.9 (11) | N1—C15—H15C | 109.5 |
| C6—C7—H7 | 118.0 (11) | H15A—C15—H15C | 109.5 |
| C7—C8—C3 | 119.17 (16) | H15B—C15—H15C | 109.5 |
| C7—C8—H8 | 121.1 (10) | ||
| C4—N1—C1—C2 | −0.64 (17) | N1—C4—C5—C6 | −179.45 (15) |
| C15—N1—C1—C2 | −176.48 (16) | C3—C4—C5—C6 | 1.5 (2) |
| C4—N1—C1—C9 | 177.49 (13) | C4—C5—C6—C7 | 0.1 (3) |
| C15—N1—C1—C9 | 1.7 (2) | C5—C6—C7—C8 | −1.5 (3) |
| C1—N1—C4—C5 | −178.07 (15) | C3—C8—C7—C6 | 1.1 (3) |
| C15—N1—C4—C5 | −2.1 (3) | C10—C9—C1—C2 | −135.81 (18) |
| C1—N1—C4—C3 | 1.11 (16) | C14—C9—C1—C2 | 43.6 (2) |
| C15—N1—C4—C3 | 177.11 (15) | C10—C9—C1—N1 | 46.4 (2) |
| N1—C1—C2—C3 | −0.08 (17) | C14—C9—C1—N1 | −134.12 (16) |
| C9—C1—C2—C3 | −178.07 (14) | C10—C9—C14—C13 | −2.2 (2) |
| C8—C3—C2—C1 | −179.38 (17) | C1—C9—C14—C13 | 178.35 (15) |
| C4—C3—C2—C1 | 0.75 (17) | C14—C9—C10—C11 | 2.5 (2) |
| C8—C3—C4—N1 | 178.97 (13) | C1—C9—C10—C11 | −178.03 (15) |
| C2—C3—C4—N1 | −1.14 (16) | C9—C10—C11—C12 | −0.4 (3) |
| C8—C3—C4—C5 | −1.8 (2) | C14—C13—C12—C11 | 2.4 (3) |
| C2—C3—C4—C5 | 178.11 (15) | C13—C12—C11—C10 | −2.1 (3) |
| C4—C3—C8—C7 | 0.4 (2) | C9—C14—C13—C12 | −0.3 (3) |
| C2—C3—C8—C7 | −179.42 (17) |
