2-Methyl-3-{2-nitro-1-[2-(prop-2-yn-1-yl-oxy)phen-yl]eth-yl}-1H-indole.

In the title compound, C(20)H(18)N(2)O(3), the indole unit is essentially planar, with a maximum deviation of 0.0197 (18) Å for the N atom and forms a dihedral angle of 78.09 (9)° with the propyne-subsituted phenyl ring. The propyne group is almost linear, the C-C C angle being 176.5 (2)°, and is also in the flagpole position on the O atom. In the crystal, mol-ecules are linked via N-H⋯O and C-H⋯O inter-molecular hydrogen bonds involving the nitro-group O atoms as acceptors.

Related literature

For general backround to indoles, see: Gribble (1996 ▶); Mathiesen et al. (2005 ▶). For related structures, see: Narayanan et al. (2011 ▶); Ranjith et al. (2010 ▶). For bond-length distortions, see: Allen (1981 ▶).

Experimental

Crystal data

C20H18N2O3

M = 334.36

Tetragonal,

a = 23.3474 (7) Å

c = 12.8536 (7) Å

V = 7006.5 (5) Å3

Z = 16

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

31091 measured reflections

3954 independent reflections

2629 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.149

S = 1.03

3954 reflections

231 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036907/rk2291sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036907/rk2291Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036907/rk2291Isup3.cml

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

C20H18N2O3	Dx = 1.268 Mg m−3
Mr = 334.36	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 3954 reflections
Hall symbol: -I 4ad	θ = 2.5–27.3°
a = 23.3474 (7) Å	µ = 0.09 mm−1
c = 12.8536 (7) Å	T = 295 K
V = 7006.5 (5) Å3	Block, brown
Z = 16	0.30 × 0.25 × 0.20 mm
F(000) = 2816

Bruker Kappa APEXII diffractometer	2629 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tube	Rint = 0.034
graphite	θmax = 27.3°, θmin = 2.5°
ω and φ scans	h = −30→30
31091 measured reflections	k = −30→30
3954 independent reflections	l = −16→16

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.061P)2 + 4.4075P] where P = (Fo2 + 2Fc2)/3
3954 reflections	(Δ/σ)max = 0.001
231 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.57180 (8)	0.58359 (8)	0.28887 (15)	0.0561 (5)
H1	0.6050	0.5907	0.2511	0.067*
C2	0.54456 (11)	0.62723 (10)	0.34038 (18)	0.0739 (6)
H2	0.5595	0.6641	0.3365	0.089*
C3	0.49531 (12)	0.61764 (12)	0.39812 (19)	0.0837 (7)
H3	0.4784	0.6480	0.4335	0.100*
C4	0.47114 (10)	0.56413 (12)	0.40392 (16)	0.0746 (6)
H4	0.4379	0.5577	0.4421	0.090*
C5	0.49805 (8)	0.52014 (9)	0.35072 (14)	0.0567 (5)
C6	0.54906 (7)	0.52835 (8)	0.29372 (12)	0.0471 (4)
C7	0.56448 (7)	0.47343 (7)	0.25110 (12)	0.0456 (4)
C8	0.52332 (8)	0.43530 (9)	0.28289 (14)	0.0574 (5)
C9	0.51646 (12)	0.37274 (10)	0.2625 (2)	0.0854 (7)
H9A	0.4937	0.3559	0.3167	0.128*
H9B	0.5535	0.3548	0.2610	0.128*
H9C	0.4978	0.3673	0.1967	0.128*
C10	0.61764 (7)	0.45897 (7)	0.19019 (12)	0.0461 (4)
H10	0.6150	0.4185	0.1703	0.055*
C11	0.67081 (8)	0.46567 (9)	0.25835 (14)	0.0556 (5)
H11A	0.7049	0.4568	0.2182	0.067*
H11B	0.6738	0.5049	0.2826	0.067*
C12	0.62457 (7)	0.49375 (7)	0.09048 (12)	0.0466 (4)
C13	0.66337 (9)	0.53799 (9)	0.07902 (15)	0.0608 (5)
H13	0.6877	0.5469	0.1339	0.073*
C14	0.66695 (11)	0.56947 (10)	−0.01207 (17)	0.0747 (6)
H14	0.6936	0.5989	−0.0182	0.090*
C15	0.63101 (11)	0.55691 (10)	−0.09283 (17)	0.0741 (6)
H15	0.6327	0.5785	−0.1536	0.089*
C16	0.59234 (10)	0.51273 (9)	−0.08517 (14)	0.0627 (5)
H16	0.5681	0.5044	−0.1406	0.075*
C17	0.58959 (8)	0.48052 (8)	0.00541 (13)	0.0486 (4)
C18	0.52168 (9)	0.41607 (9)	−0.06941 (14)	0.0626 (5)
H18A	0.5476	0.4081	−0.1266	0.075*
H18B	0.4952	0.4458	−0.0912	0.075*
C19	0.49038 (9)	0.36474 (10)	−0.04196 (16)	0.0655 (5)
C20	0.46475 (12)	0.32315 (15)	−0.0253 (2)	0.0902 (8)
N1	0.48348 (7)	0.46368 (8)	0.34151 (12)	0.0659 (5)
H1A	0.4536	0.4482	0.3687	0.079*
N2	0.66652 (9)	0.42633 (9)	0.34832 (17)	0.0796 (6)
O1	0.66570 (12)	0.44706 (10)	0.43438 (16)	0.1362 (10)
O2	0.66138 (13)	0.37606 (8)	0.3327 (2)	0.1423 (10)
O3	0.55338 (6)	0.43482 (6)	0.01938 (9)	0.0586 (4)
H20	0.4442 (13)	0.2919 (12)	−0.011 (2)	0.118 (11)*

	U11	U22	U33	U12	U13	U23
C1	0.0576 (11)	0.0581 (11)	0.0526 (10)	0.0033 (9)	−0.0041 (9)	0.0056 (9)
C2	0.0856 (16)	0.0634 (13)	0.0727 (14)	0.0126 (11)	−0.0077 (12)	0.0021 (11)
C3	0.0949 (18)	0.0863 (17)	0.0700 (15)	0.0366 (14)	−0.0004 (13)	−0.0033 (13)
C4	0.0628 (13)	0.1061 (19)	0.0551 (12)	0.0235 (13)	0.0091 (10)	0.0114 (12)
C5	0.0506 (10)	0.0771 (13)	0.0423 (9)	0.0048 (9)	−0.0010 (8)	0.0119 (9)
C6	0.0461 (9)	0.0606 (10)	0.0346 (8)	0.0030 (8)	−0.0055 (7)	0.0109 (7)
C7	0.0482 (9)	0.0536 (10)	0.0351 (8)	−0.0032 (7)	−0.0042 (7)	0.0098 (7)
C8	0.0602 (11)	0.0666 (12)	0.0453 (9)	−0.0122 (9)	−0.0003 (8)	0.0121 (9)
C9	0.1018 (18)	0.0704 (15)	0.0841 (16)	−0.0319 (13)	0.0091 (14)	0.0090 (12)
C10	0.0505 (9)	0.0473 (9)	0.0405 (8)	0.0002 (7)	−0.0030 (7)	0.0045 (7)
C11	0.0536 (10)	0.0630 (11)	0.0503 (10)	0.0055 (9)	−0.0033 (8)	0.0066 (9)
C12	0.0496 (9)	0.0515 (9)	0.0387 (8)	0.0034 (7)	0.0057 (7)	0.0033 (7)
C13	0.0667 (12)	0.0661 (12)	0.0497 (10)	−0.0107 (9)	0.0081 (9)	0.0049 (9)
C14	0.0923 (16)	0.0709 (14)	0.0610 (13)	−0.0162 (12)	0.0210 (12)	0.0106 (11)
C15	0.1057 (18)	0.0701 (13)	0.0466 (11)	0.0043 (12)	0.0202 (11)	0.0167 (10)
C16	0.0816 (14)	0.0664 (12)	0.0400 (10)	0.0116 (11)	0.0039 (9)	0.0073 (9)
C17	0.0527 (10)	0.0539 (10)	0.0392 (8)	0.0083 (8)	0.0044 (7)	0.0031 (7)
C18	0.0674 (12)	0.0758 (13)	0.0447 (10)	0.0065 (10)	−0.0129 (9)	−0.0074 (9)
C19	0.0575 (12)	0.0849 (15)	0.0542 (11)	0.0005 (11)	−0.0083 (9)	−0.0130 (11)
C20	0.0810 (17)	0.109 (2)	0.0808 (17)	−0.0283 (17)	−0.0087 (13)	−0.0050 (16)
N1	0.0560 (9)	0.0874 (12)	0.0542 (9)	−0.0139 (9)	0.0098 (8)	0.0156 (9)
N2	0.0929 (14)	0.0688 (12)	0.0771 (13)	−0.0006 (10)	−0.0388 (11)	0.0223 (10)
O1	0.211 (3)	0.1348 (18)	0.0629 (11)	−0.0503 (17)	−0.0414 (14)	0.0353 (12)
O2	0.209 (3)	0.0599 (11)	0.158 (2)	0.0096 (13)	−0.0778 (19)	0.0308 (12)
O3	0.0645 (8)	0.0686 (8)	0.0428 (7)	−0.0091 (6)	−0.0115 (6)	0.0054 (6)

C1—C2	1.371 (3)	C11—H11A	0.9700
C1—C6	1.396 (3)	C11—H11B	0.9700
C1—H1	0.9300	C12—C13	1.382 (3)
C2—C3	1.387 (3)	C12—C17	1.399 (2)
C2—H2	0.9300	C13—C14	1.385 (3)
C3—C4	1.373 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.367 (3)
C4—C5	1.384 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.374 (3)
C5—N1	1.367 (3)	C15—H15	0.9300
C5—C6	1.411 (2)	C16—C17	1.387 (2)
C6—C7	1.440 (3)	C16—H16	0.9300
C7—C8	1.372 (2)	C17—O3	1.373 (2)
C7—C10	1.506 (2)	C18—O3	1.429 (2)
C8—N1	1.368 (3)	C18—C19	1.447 (3)
C8—C9	1.492 (3)	C18—H18A	0.9700
C9—H9A	0.9600	C18—H18B	0.9700
C9—H9B	0.9600	C19—C20	1.160 (4)
C9—H9C	0.9600	C20—H20	0.89 (3)
C10—C12	1.526 (2)	N1—H1A	0.8600
C10—C11	1.528 (2)	N2—O2	1.197 (3)
C10—H10	0.9800	N2—O1	1.208 (3)
C11—N2	1.480 (3)
C2—C1—C6	119.24 (19)	C10—C11—H11A	109.8
C2—C1—H1	120.4	N2—C11—H11B	109.8
C6—C1—H1	120.4	C10—C11—H11B	109.8
C1—C2—C3	121.5 (2)	H11A—C11—H11B	108.3
C1—C2—H2	119.2	C13—C12—C17	117.67 (16)
C3—C2—H2	119.2	C13—C12—C10	123.84 (16)
C4—C3—C2	121.1 (2)	C17—C12—C10	118.49 (15)
C4—C3—H3	119.4	C12—C13—C14	121.8 (2)
C2—C3—H3	119.4	C12—C13—H13	119.1
C3—C4—C5	117.5 (2)	C14—C13—H13	119.1
C3—C4—H4	121.3	C15—C14—C13	119.4 (2)
C5—C4—H4	121.3	C15—C14—H14	120.3
N1—C5—C4	130.19 (19)	C13—C14—H14	120.3
N1—C5—C6	107.22 (17)	C14—C15—C16	120.67 (19)
C4—C5—C6	122.6 (2)	C14—C15—H15	119.7
C1—C6—C5	118.00 (17)	C16—C15—H15	119.7
C1—C6—C7	135.28 (16)	C15—C16—C17	119.8 (2)
C5—C6—C7	106.71 (16)	C15—C16—H16	120.1
C8—C7—C6	106.82 (16)	C17—C16—H16	120.1
C8—C7—C10	125.92 (17)	O3—C17—C16	124.02 (17)
C6—C7—C10	127.11 (15)	O3—C17—C12	115.38 (14)
N1—C8—C7	109.02 (18)	C16—C17—C12	120.60 (18)
N1—C8—C9	119.85 (18)	O3—C18—C19	108.69 (16)
C7—C8—C9	131.1 (2)	O3—C18—H18A	110.0
C8—C9—H9A	109.5	C19—C18—H18A	110.0
C8—C9—H9B	109.5	O3—C18—H18B	110.0
H9A—C9—H9B	109.5	C19—C18—H18B	110.0
C8—C9—H9C	109.5	H18A—C18—H18B	108.3
H9A—C9—H9C	109.5	C20—C19—C18	176.5 (2)
H9B—C9—H9C	109.5	C19—C20—H20	178 (2)
C7—C10—C12	113.88 (13)	C5—N1—C8	110.22 (15)
C7—C10—C11	110.41 (14)	C5—N1—H1A	124.9
C12—C10—C11	109.95 (14)	C8—N1—H1A	124.9
C7—C10—H10	107.4	O2—N2—O1	123.0 (2)
C12—C10—H10	107.4	O2—N2—C11	119.0 (2)
C11—C10—H10	107.4	O1—N2—C11	117.9 (2)
N2—C11—C10	109.25 (15)	C17—O3—C18	116.90 (14)
N2—C11—H11A	109.8
C6—C1—C2—C3	0.7 (3)	C7—C10—C12—C13	105.5 (2)
C1—C2—C3—C4	−1.5 (4)	C11—C10—C12—C13	−19.0 (2)
C2—C3—C4—C5	0.5 (3)	C7—C10—C12—C17	−74.2 (2)
C3—C4—C5—N1	−179.0 (2)	C11—C10—C12—C17	161.27 (16)
C3—C4—C5—C6	1.3 (3)	C17—C12—C13—C14	1.7 (3)
C2—C1—C6—C5	1.0 (3)	C10—C12—C13—C14	−178.07 (18)
C2—C1—C6—C7	179.47 (19)	C12—C13—C14—C15	0.4 (3)
N1—C5—C6—C1	178.18 (15)	C13—C14—C15—C16	−1.3 (4)
C4—C5—C6—C1	−2.0 (3)	C14—C15—C16—C17	0.1 (3)
N1—C5—C6—C7	−0.71 (19)	C15—C16—C17—O3	−178.42 (18)
C4—C5—C6—C7	179.09 (17)	C15—C16—C17—C12	2.1 (3)
C1—C6—C7—C8	−178.48 (19)	C13—C12—C17—O3	177.55 (16)
C5—C6—C7—C8	0.12 (18)	C10—C12—C17—O3	−2.7 (2)
C1—C6—C7—C10	5.8 (3)	C13—C12—C17—C16	−2.9 (3)
C5—C6—C7—C10	−175.64 (15)	C10—C12—C17—C16	176.84 (16)
C6—C7—C8—N1	0.52 (19)	C4—C5—N1—C8	−178.7 (2)
C10—C7—C8—N1	176.34 (15)	C6—C5—N1—C8	1.1 (2)
C6—C7—C8—C9	179.6 (2)	C7—C8—N1—C5	−1.0 (2)
C10—C7—C8—C9	−4.6 (3)	C9—C8—N1—C5	179.79 (18)
C8—C7—C10—C12	125.70 (18)	C10—C11—N2—O2	58.0 (3)
C6—C7—C10—C12	−59.3 (2)	C10—C11—N2—O1	−118.6 (2)
C8—C7—C10—C11	−110.05 (19)	C16—C17—O3—C18	7.2 (3)
C6—C7—C10—C11	64.9 (2)	C12—C17—O3—C18	−173.23 (16)
C7—C10—C11—N2	60.3 (2)	C19—C18—O3—C17	174.73 (16)
C12—C10—C11—N2	−173.18 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.14	2.997 (2)	173.
C11—H11A···O1ii	0.97	2.52	3.433 (3)	157.
C15—H15···O1iii	0.93	2.57	3.315 (3)	137.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.14	2.997 (2)	173
C11—H11A⋯O1ii	0.97	2.52	3.433 (3)	157
C15—H15⋯O1iii	0.93	2.57	3.315 (3)	137

Symmetry codes: (i) ; (ii) ; (iii) .