1-(2-Methyl-benz-yl)-1H-indole-3-carbaldehyde.

In the title compound, C(17)H(15)NO, the benzene ring and the indole system are almost perpendicular, making a dihedral angle of 87.82 (6)°. The crystal packing is stabilized by C-H⋯O and π-π stacking inter-actions with centroid-centroid distances of 3.592 (4) Å between the pyrrole and the benzene rings in the indole systems of neighboring mol-ecules.

Related literature

For general background to the chemistry and anti-inflammatory activity of carboxylic acid derivatives, see: Andreani et al. (1994 ▶).

Experimental

Crystal data

C17H15NO

M = 249.30

Monoclinic,

a = 10.5251 (3) Å

b = 15.4352 (5) Å

c = 8.2335 (2) Å

β = 99.214 (3)°

V = 1320.33 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.28 × 0.25 × 0.20 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.981, T max = 1.000

5468 measured reflections

2699 independent reflections

1928 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.117

S = 1.04

2699 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov, 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010306/bt5840sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010306/bt5840Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010306/bt5840Isup3.cml

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

C17H15NO	F(000) = 528
Mr = 249.30	Dx = 1.254 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
a = 10.5251 (3) Å	Cell parameters from 1937 reflections
b = 15.4352 (5) Å	θ = 3.2–29.1°
c = 8.2335 (2) Å	µ = 0.08 mm−1
β = 99.214 (3)°	T = 293 K
V = 1320.33 (7) Å3	Block, colorless
Z = 4	0.28 × 0.25 × 0.20 mm

Agilent Xcalibur Eos diffractometer	2699 independent reflections
Radiation source: fine-focus sealed tube	1928 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.2°
ω scans	h = −11→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→19
Tmin = 0.981, Tmax = 1.000	l = −10→4
5468 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.2065P] where P = (Fo2 + 2Fc2)/3
2699 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.02058 (15)	0.14964 (11)	−0.33644 (17)	0.0895 (5)
N1	0.21128 (12)	0.01830 (9)	0.14071 (15)	0.0439 (3)
C1	0.18887 (13)	−0.04418 (11)	0.01839 (19)	0.0404 (4)
C2	0.13295 (13)	−0.00278 (11)	−0.12762 (19)	0.0415 (4)
C3	0.12187 (14)	0.08699 (11)	−0.0886 (2)	0.0457 (4)
C4	0.17018 (15)	0.09542 (11)	0.0760 (2)	0.0475 (4)
H4	0.1739	0.1472	0.1344	0.057*
C5	0.10025 (15)	−0.05289 (13)	−0.2699 (2)	0.0506 (4)
H5	0.0639	−0.0273	−0.3687	0.061*
C6	0.12281 (16)	−0.14068 (13)	−0.2611 (2)	0.0573 (5)
H6	0.1010	−0.1744	−0.3549	0.069*
C7	0.17749 (16)	−0.17975 (12)	−0.1149 (2)	0.0567 (5)
H7	0.1910	−0.2393	−0.1126	0.068*
C8	0.21221 (15)	−0.13246 (11)	0.0266 (2)	0.0503 (4)
H8	0.2499	−0.1587	0.1242	0.060*
C9	0.06793 (18)	0.15646 (14)	−0.1918 (3)	0.0642 (5)
H9	0.0690	0.2113	−0.1449	0.077*
C10	0.26384 (17)	0.00142 (12)	0.31387 (19)	0.0536 (5)
H10A	0.3153	−0.0510	0.3210	0.064*
H10B	0.1933	−0.0082	0.3745	0.064*
C11	0.34564 (15)	0.07493 (11)	0.39236 (19)	0.0455 (4)
C12	0.46514 (15)	0.09284 (11)	0.34816 (19)	0.0448 (4)
C13	0.53745 (17)	0.15965 (12)	0.4283 (2)	0.0565 (5)
H13	0.6176	0.1721	0.4002	0.068*
C14	0.4941 (2)	0.20792 (14)	0.5479 (2)	0.0679 (6)
H14	0.5445	0.2525	0.5997	0.082*
C15	0.3765 (2)	0.19041 (15)	0.5909 (3)	0.0744 (6)
H15	0.3467	0.2228	0.6722	0.089*
C16	0.30237 (18)	0.12415 (14)	0.5125 (2)	0.0637 (5)
H16	0.2221	0.1125	0.5411	0.076*
C17	0.51550 (17)	0.04237 (15)	0.2160 (2)	0.0666 (6)
H17A	0.5075	−0.0185	0.2360	0.100*
H17B	0.6044	0.0565	0.2168	0.100*
H17C	0.4667	0.0568	0.1108	0.100*

	U11	U22	U33	U12	U13	U23
O1	0.1027 (11)	0.1071 (13)	0.0562 (9)	0.0489 (10)	0.0050 (8)	0.0189 (9)
N1	0.0436 (7)	0.0468 (8)	0.0395 (7)	−0.0044 (6)	0.0014 (6)	0.0004 (7)
C1	0.0344 (8)	0.0448 (10)	0.0419 (9)	−0.0048 (7)	0.0059 (6)	−0.0003 (8)
C2	0.0307 (7)	0.0519 (10)	0.0418 (9)	−0.0009 (7)	0.0059 (6)	0.0016 (8)
C3	0.0377 (8)	0.0520 (11)	0.0471 (9)	0.0042 (7)	0.0054 (7)	0.0049 (8)
C4	0.0461 (9)	0.0446 (10)	0.0515 (10)	−0.0020 (7)	0.0070 (8)	−0.0009 (8)
C5	0.0386 (8)	0.0719 (13)	0.0404 (9)	−0.0027 (8)	0.0031 (7)	−0.0013 (9)
C6	0.0509 (10)	0.0663 (13)	0.0550 (11)	−0.0111 (9)	0.0098 (8)	−0.0169 (10)
C7	0.0570 (10)	0.0472 (11)	0.0663 (12)	−0.0060 (8)	0.0109 (9)	−0.0063 (9)
C8	0.0495 (9)	0.0482 (11)	0.0523 (10)	−0.0042 (8)	0.0052 (8)	0.0054 (9)
C9	0.0626 (12)	0.0655 (13)	0.0659 (13)	0.0204 (10)	0.0145 (10)	0.0106 (11)
C10	0.0586 (10)	0.0626 (12)	0.0381 (9)	−0.0110 (9)	0.0031 (8)	0.0043 (8)
C11	0.0486 (9)	0.0514 (10)	0.0348 (8)	−0.0002 (8)	0.0020 (7)	0.0014 (8)
C12	0.0459 (9)	0.0520 (10)	0.0345 (8)	0.0019 (8)	0.0004 (7)	0.0041 (8)
C13	0.0511 (10)	0.0644 (12)	0.0505 (10)	−0.0082 (9)	−0.0028 (8)	0.0026 (10)
C14	0.0765 (13)	0.0592 (13)	0.0622 (12)	−0.0081 (11)	−0.0073 (11)	−0.0119 (11)
C15	0.0856 (15)	0.0753 (15)	0.0612 (13)	0.0110 (12)	0.0082 (11)	−0.0251 (11)
C16	0.0579 (11)	0.0806 (15)	0.0541 (11)	0.0017 (10)	0.0133 (9)	−0.0112 (10)
C17	0.0572 (11)	0.0863 (16)	0.0584 (12)	0.0029 (10)	0.0161 (9)	−0.0093 (11)

O1—C9	1.220 (2)	C9—H9	0.9300
N1—C1	1.387 (2)	C10—H10A	0.9700
N1—C4	1.347 (2)	C10—H10B	0.9700
N1—C10	1.4677 (19)	C10—C11	1.506 (2)
C1—C2	1.405 (2)	C11—C12	1.392 (2)
C1—C8	1.384 (2)	C11—C16	1.381 (2)
C2—C3	1.431 (2)	C12—C13	1.385 (2)
C2—C5	1.400 (2)	C12—C17	1.502 (2)
C3—C4	1.375 (2)	C13—H13	0.9300
C3—C9	1.428 (2)	C13—C14	1.370 (3)
C4—H4	0.9300	C14—H14	0.9300
C5—H5	0.9300	C14—C15	1.367 (3)
C5—C6	1.376 (3)	C15—H15	0.9300
C6—H6	0.9300	C15—C16	1.382 (3)
C6—C7	1.386 (3)	C16—H16	0.9300
C7—H7	0.9300	C17—H17A	0.9600
C7—C8	1.374 (2)	C17—H17B	0.9600
C8—H8	0.9300	C17—H17C	0.9600
C1—N1—C10	125.15 (14)	N1—C10—H10A	109.1
C4—N1—C1	108.69 (13)	N1—C10—H10B	109.1
C4—N1—C10	126.06 (14)	N1—C10—C11	112.57 (14)
N1—C1—C2	107.72 (14)	H10A—C10—H10B	107.8
C8—C1—N1	129.84 (15)	C11—C10—H10A	109.1
C8—C1—C2	122.44 (15)	C11—C10—H10B	109.1
C1—C2—C3	106.65 (14)	C12—C11—C10	121.05 (15)
C5—C2—C1	118.56 (16)	C16—C11—C10	119.37 (16)
C5—C2—C3	134.79 (16)	C16—C11—C12	119.57 (16)
C4—C3—C2	106.38 (14)	C11—C12—C17	121.66 (15)
C4—C3—C9	124.34 (17)	C13—C12—C11	118.30 (15)
C9—C3—C2	129.24 (16)	C13—C12—C17	120.04 (16)
N1—C4—C3	110.55 (15)	C12—C13—H13	119.1
N1—C4—H4	124.7	C14—C13—C12	121.77 (17)
C3—C4—H4	124.7	C14—C13—H13	119.1
C2—C5—H5	120.6	C13—C14—H14	120.1
C6—C5—C2	118.87 (16)	C15—C14—C13	119.88 (18)
C6—C5—H5	120.6	C15—C14—H14	120.1
C5—C6—H6	119.4	C14—C15—H15	120.3
C5—C6—C7	121.23 (17)	C14—C15—C16	119.49 (18)
C7—C6—H6	119.4	C16—C15—H15	120.3
C6—C7—H7	119.3	C11—C16—C15	121.00 (18)
C8—C7—C6	121.48 (18)	C11—C16—H16	119.5
C8—C7—H7	119.3	C15—C16—H16	119.5
C1—C8—H8	121.3	C12—C17—H17A	109.5
C7—C8—C1	117.41 (16)	C12—C17—H17B	109.5
C7—C8—H8	121.3	C12—C17—H17C	109.5
O1—C9—C3	125.3 (2)	H17A—C17—H17B	109.5
O1—C9—H9	117.4	H17A—C17—H17C	109.5
C3—C9—H9	117.4	H17B—C17—H17C	109.5
N1—C1—C2—C3	−0.28 (16)	C5—C2—C3—C9	1.2 (3)
N1—C1—C2—C5	−179.55 (13)	C5—C6—C7—C8	−0.5 (3)
N1—C1—C8—C7	178.63 (15)	C6—C7—C8—C1	0.9 (2)
N1—C10—C11—C12	−69.9 (2)	C8—C1—C2—C3	179.02 (14)
N1—C10—C11—C16	111.41 (18)	C8—C1—C2—C5	−0.3 (2)
C1—N1—C4—C3	−0.86 (18)	C9—C3—C4—N1	178.46 (15)
C1—N1—C10—C11	147.04 (15)	C10—N1—C1—C2	177.28 (13)
C1—C2—C3—C4	−0.23 (16)	C10—N1—C1—C8	−1.9 (2)
C1—C2—C3—C9	−177.87 (16)	C10—N1—C4—C3	−177.41 (13)
C1—C2—C5—C6	0.6 (2)	C10—C11—C12—C13	−178.10 (15)
C2—C1—C8—C7	−0.5 (2)	C10—C11—C12—C17	2.5 (2)
C2—C3—C4—N1	0.67 (17)	C10—C11—C16—C15	178.00 (18)
C2—C3—C9—O1	0.0 (3)	C11—C12—C13—C14	−0.3 (3)
C2—C5—C6—C7	−0.3 (2)	C12—C11—C16—C15	−0.7 (3)
C3—C2—C5—C6	−178.37 (16)	C12—C13—C14—C15	0.1 (3)
C4—N1—C1—C2	0.69 (16)	C13—C14—C15—C16	−0.2 (3)
C4—N1—C1—C8	−178.54 (15)	C14—C15—C16—C11	0.5 (3)
C4—N1—C10—C11	−37.0 (2)	C16—C11—C12—C13	0.5 (2)
C4—C3—C9—O1	−177.28 (17)	C16—C11—C12—C17	−178.81 (16)
C5—C2—C3—C4	178.87 (16)	C17—C12—C13—C14	179.10 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1i	0.93	2.56	3.418 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O1i	0.93	2.56	3.418 (2)	154

Symmetry code: (i) .