2-(4-Fluoro-phen-yl)-3-methyl-1H-indole.

The indole N-H hydrogen in the title compound, C(15)H(12)FN, does not display classical hydrogen bonding. Rather it forms an interaction with the π system of an adjacent indole, resulting in weakly inter-acting chains along the [001] direction.

Related literature

The title compound has previously been prepared by Buu-Hoi & Jacquignon (1949 ▶) and by Kraus & Guo (2009 ▶). For the synthesis of the starting material, 4-fluoro-N-(2-oxo-2-phenyl­eth­yl)benzamide, see: Moriya et al. (1986 ▶). There are no structures of closely related compounds in the literature. For some similar compounds, see: Schmelter et al. (1973 ▶); Konno et al. (2004 ▶); Kumar & Liu (2006 ▶).

Experimental

Crystal data

C15H12FN

M = 225.26

Monoclinic,

a = 7.790 (3) Å

b = 17.125 (6) Å

c = 8.811 (4) Å

β = 110.274 (9)°

V = 1102.7 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 93 K

0.25 × 0.20 × 0.15 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2010 ▶) T min = 0.706, T max = 1.000

7380 measured reflections

2361 independent reflections

1703 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.195

S = 1.07

2361 reflections

160 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku, 2010 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811021325/si2359sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021325/si2359Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811021325/si2359Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H12FN	F(000) = 472
Mr = 225.26	Dx = 1.357 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3217 reflections
a = 7.790 (3) Å	θ = 2.4–28.3°
b = 17.125 (6) Å	µ = 0.09 mm−1
c = 8.811 (4) Å	T = 93 K
β = 110.274 (9)°	Platelet, colorless
V = 1102.7 (8) Å3	0.25 × 0.20 × 0.15 mm
Z = 4

Rigaku Mercury CCD diffractometer	2361 independent reflections
Radiation source: rotating anode	1703 reflections with I > 2σ(I)
confocal	Rint = 0.049
Detector resolution: 14.7059 pixels mm-1	θmax = 28.7°, θmin = 2.4°
ω and φ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010)	k = −16→23
Tmin = 0.706, Tmax = 1.000	l = −11→10
7380 measured reflections

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)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.195	w = 1/[σ2(Fo2) + (0.1147P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2361 reflections	Δρmax = 0.31 e Å−3
160 parameters	Δρmin = −0.21 e Å−3
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.052 (13)

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. A distance restraint was applied to the N—H bond.

	x	y	z	Uiso*/Ueq
F1	0.44463 (18)	0.36586 (7)	0.14270 (16)	0.0629 (5)
N1	−0.1358 (2)	0.33607 (9)	0.5104 (2)	0.0416 (5)
H1	−0.190 (3)	0.3064 (13)	0.416 (2)	0.070 (7)*
C1	0.0281 (2)	0.37720 (10)	0.5467 (2)	0.0373 (5)
C2	0.0708 (2)	0.41011 (10)	0.6983 (2)	0.0392 (5)
C3	−0.0707 (2)	0.38743 (10)	0.7584 (2)	0.0386 (5)
C4	−0.1007 (3)	0.40028 (10)	0.9045 (2)	0.0427 (5)
H4	−0.0164	0.4305	0.9878	0.051*
C5	−0.2529 (3)	0.36883 (11)	0.9262 (2)	0.0456 (5)
H5	−0.2725	0.3767	1.0256	0.055*
C6	−0.3796 (3)	0.32527 (11)	0.8028 (2)	0.0470 (5)
H6	−0.4854	0.3053	0.8195	0.056*
C7	−0.3545 (2)	0.31077 (11)	0.6581 (2)	0.0445 (5)
H7	−0.4404	0.2809	0.5754	0.053*
C8	−0.1987 (2)	0.34150 (10)	0.6377 (2)	0.0392 (5)
C9	0.2314 (3)	0.46041 (11)	0.7870 (2)	0.0466 (5)
H9A	0.3395	0.4421	0.7648	0.070*
H9B	0.2545	0.4574	0.9034	0.070*
H9C	0.2052	0.5146	0.7507	0.070*
C10	0.1309 (2)	0.37612 (10)	0.4355 (2)	0.0379 (5)
C11	0.1282 (2)	0.30989 (11)	0.3413 (2)	0.0420 (5)
H11	0.0543	0.2665	0.3462	0.050*
C12	0.2309 (2)	0.30642 (11)	0.2413 (2)	0.0456 (5)
H12	0.2274	0.2616	0.1766	0.055*
C13	0.3388 (3)	0.36986 (12)	0.2380 (2)	0.0459 (5)
C14	0.3432 (3)	0.43669 (11)	0.3255 (2)	0.0446 (5)
H14	0.4166	0.4799	0.3188	0.054*
C15	0.2382 (2)	0.43944 (10)	0.4235 (2)	0.0415 (5)
H15	0.2390	0.4854	0.4840	0.050*

	U11	U22	U33	U12	U13	U23
F1	0.0641 (9)	0.0696 (9)	0.0655 (9)	0.0056 (7)	0.0357 (7)	0.0017 (7)
N1	0.0344 (9)	0.0434 (9)	0.0440 (10)	−0.0072 (6)	0.0099 (7)	−0.0019 (8)
C1	0.0319 (9)	0.0299 (8)	0.0474 (11)	−0.0007 (7)	0.0101 (8)	0.0018 (8)
C2	0.0325 (9)	0.0340 (10)	0.0482 (11)	0.0003 (7)	0.0104 (8)	0.0014 (8)
C3	0.0349 (9)	0.0319 (9)	0.0461 (11)	0.0048 (7)	0.0104 (8)	0.0052 (8)
C4	0.0434 (11)	0.0340 (10)	0.0484 (12)	0.0027 (8)	0.0128 (9)	0.0020 (9)
C5	0.0476 (12)	0.0420 (11)	0.0487 (12)	0.0023 (8)	0.0183 (10)	0.0052 (9)
C6	0.0396 (11)	0.0448 (11)	0.0579 (13)	0.0000 (8)	0.0187 (9)	0.0100 (10)
C7	0.0363 (10)	0.0451 (11)	0.0479 (12)	−0.0021 (8)	0.0093 (9)	0.0062 (9)
C8	0.0322 (9)	0.0367 (10)	0.0453 (11)	0.0011 (7)	0.0091 (8)	0.0038 (9)
C9	0.0388 (10)	0.0448 (11)	0.0523 (12)	−0.0058 (8)	0.0107 (9)	−0.0037 (10)
C10	0.0315 (9)	0.0369 (10)	0.0412 (11)	0.0024 (7)	0.0071 (8)	0.0024 (8)
C11	0.0378 (10)	0.0382 (10)	0.0450 (11)	−0.0014 (7)	0.0080 (8)	0.0001 (9)
C12	0.0424 (11)	0.0450 (12)	0.0444 (12)	0.0038 (8)	0.0085 (9)	−0.0039 (9)
C13	0.0397 (11)	0.0548 (12)	0.0440 (11)	0.0073 (9)	0.0156 (9)	0.0043 (10)
C14	0.0371 (10)	0.0420 (11)	0.0533 (12)	0.0007 (8)	0.0139 (9)	0.0079 (9)
C15	0.0353 (10)	0.0356 (10)	0.0504 (11)	0.0021 (7)	0.0106 (8)	0.0006 (9)

F1—C13	1.367 (2)	C7—C8	1.391 (3)
N1—C8	1.374 (2)	C7—H7	0.9500
N1—C1	1.395 (2)	C9—H9A	0.9800
N1—H1	0.944 (16)	C9—H9B	0.9800
C1—C2	1.380 (3)	C9—H9C	0.9800
C1—C10	1.465 (3)	C10—C15	1.395 (3)
C2—C3	1.432 (2)	C10—C11	1.402 (3)
C2—C9	1.497 (3)	C11—C12	1.382 (3)
C3—C4	1.403 (3)	C11—H11	0.9500
C3—C8	1.417 (3)	C12—C13	1.380 (3)
C4—C5	1.375 (3)	C12—H12	0.9500
C4—H4	0.9500	C13—C14	1.374 (3)
C5—C6	1.403 (3)	C14—C15	1.381 (3)
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.378 (3)	C15—H15	0.9500
C6—H6	0.9500
C8—N1—C1	109.61 (16)	C7—C8—C3	122.10 (18)
C8—N1—H1	125.6 (14)	C2—C9—H9A	109.5
C1—N1—H1	124.7 (14)	C2—C9—H9B	109.5
C2—C1—N1	108.81 (16)	H9A—C9—H9B	109.5
C2—C1—C10	130.42 (16)	C2—C9—H9C	109.5
N1—C1—C10	120.63 (17)	H9A—C9—H9C	109.5
C1—C2—C3	106.81 (16)	H9B—C9—H9C	109.5
C1—C2—C9	128.14 (17)	C15—C10—C11	118.04 (17)
C3—C2—C9	125.05 (17)	C15—C10—C1	121.45 (16)
C4—C3—C8	118.57 (17)	C11—C10—C1	120.48 (16)
C4—C3—C2	133.71 (18)	C12—C11—C10	121.30 (17)
C8—C3—C2	107.71 (17)	C12—C11—H11	119.3
C5—C4—C3	119.44 (18)	C10—C11—H11	119.3
C5—C4—H4	120.3	C13—C12—C11	118.10 (18)
C3—C4—H4	120.3	C13—C12—H12	120.9
C4—C5—C6	120.67 (18)	C11—C12—H12	120.9
C4—C5—H5	119.7	F1—C13—C14	118.92 (17)
C6—C5—H5	119.7	F1—C13—C12	118.33 (17)
C7—C6—C5	121.69 (18)	C14—C13—C12	122.75 (19)
C7—C6—H6	119.2	C13—C14—C15	118.33 (18)
C5—C6—H6	119.2	C13—C14—H14	120.8
C6—C7—C8	117.49 (18)	C15—C14—H14	120.8
C6—C7—H7	121.3	C14—C15—C10	121.43 (18)
C8—C7—H7	121.3	C14—C15—H15	119.3
N1—C8—C7	130.84 (17)	C10—C15—H15	119.3
N1—C8—C3	107.05 (16)
C8—N1—C1—C2	−0.5 (2)	C4—C3—C8—N1	−178.33 (15)
C8—N1—C1—C10	175.64 (15)	C2—C3—C8—N1	0.56 (19)
N1—C1—C2—C3	0.9 (2)	C4—C3—C8—C7	1.7 (3)
C10—C1—C2—C3	−174.81 (17)	C2—C3—C8—C7	−179.37 (16)
N1—C1—C2—C9	−178.84 (17)	C2—C1—C10—C15	−35.0 (3)
C10—C1—C2—C9	5.5 (3)	N1—C1—C10—C15	149.74 (17)
C1—C2—C3—C4	177.78 (19)	C2—C1—C10—C11	143.0 (2)
C9—C2—C3—C4	−2.5 (3)	N1—C1—C10—C11	−32.2 (2)
C1—C2—C3—C8	−0.9 (2)	C15—C10—C11—C12	1.1 (3)
C9—C2—C3—C8	178.83 (16)	C1—C10—C11—C12	−176.98 (16)
C8—C3—C4—C5	−0.6 (3)	C10—C11—C12—C13	0.8 (3)
C2—C3—C4—C5	−179.09 (18)	C11—C12—C13—F1	178.20 (17)
C3—C4—C5—C6	−1.1 (3)	C11—C12—C13—C14	−2.2 (3)
C4—C5—C6—C7	1.6 (3)	F1—C13—C14—C15	−178.86 (16)
C5—C6—C7—C8	−0.5 (3)	C12—C13—C14—C15	1.5 (3)
C1—N1—C8—C7	179.89 (19)	C13—C14—C15—C10	0.5 (3)
C1—N1—C8—C3	0.0 (2)	C11—C10—C15—C14	−1.8 (3)
C6—C7—C8—N1	178.87 (18)	C1—C10—C15—C14	176.27 (17)
C6—C7—C8—C3	−1.2 (3)

Cg is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cgi	0.94 (2)	2.99 (2)	3.791 (2)	143.(2)

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cgi	0.94 (2)	2.99 (2)	3.791 (2)	143 (2)

Symmetry code: (i) .