Ethyl 2-benzyl-1-propyl-1H-indole-3-carboxyl-ate.

In the title compound, C(21)H(23)NO(2), the dihedral angle between the indole ring system and the benzyl ring is 75.92 (9)°. The crystal packing is controlled by C-H⋯O and C-H⋯π inter-actions.

Related literature

For the synthesis of the title compound, see: Du et al. (2006 ▶). For its precursor, see: Jin et al. (2009 ▶).

Experimental

Crystal data

C21H23NO2

M = 321.40

Orthorhombic,

a = 16.231 (3) Å

b = 19.479 (4) Å

c = 5.5226 (11) Å

V = 1746.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 113 K

0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.985, T max = 0.991

13765 measured reflections

2204 independent reflections

2060 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.102

S = 1.07

2204 reflections

220 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016493/hb2963sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016493/hb2963Isup2.hkl

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

C21H23NO2	F(000) = 688
Mr = 321.40	Dx = 1.223 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5126 reflections
a = 16.231 (3) Å	θ = 2.4–27.5°
b = 19.479 (4) Å	µ = 0.08 mm−1
c = 5.5226 (11) Å	T = 113 K
V = 1746.0 (6) Å3	Needle, colourless
Z = 4	0.20 × 0.16 × 0.12 mm

Rigaku Saturn CCD area-detector diffractometer	2204 independent reflections
Radiation source: rotating anode	2060 reflections with I > 2σ(I)
confocal	Rint = 0.044
Detector resolution: 7.31 pixels mm-1	θmax = 27.5°, θmin = 2.4°
ω and φ scans	h = −21→20
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −25→25
Tmin = 0.985, Tmax = 0.991	l = −4→7
13765 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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.3147P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2204 reflections	Δρmax = 0.18 e Å−3
220 parameters	Δρmin = −0.15 e Å−3
1 restraint	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (4)

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	0.38761 (9)	0.34048 (8)	0.2851 (4)	0.0430 (5)
O2	0.45086 (8)	0.40505 (7)	0.0042 (3)	0.0357 (4)
N1	0.62712 (10)	0.24714 (8)	0.3130 (4)	0.0294 (4)
C1	0.66004 (12)	0.28279 (10)	0.1183 (4)	0.0300 (5)
C2	0.73763 (13)	0.27623 (11)	0.0133 (5)	0.0355 (5)
H2	0.7768	0.2440	0.0718	0.043*
C3	0.75495 (13)	0.31898 (11)	−0.1805 (5)	0.0392 (6)
H3	0.8075	0.3164	−0.2557	0.047*
C4	0.69695 (14)	0.36590 (11)	−0.2680 (5)	0.0383 (6)
H4	0.7107	0.3941	−0.4023	0.046*
C5	0.62019 (13)	0.37209 (10)	−0.1635 (5)	0.0339 (5)
H5	0.5813	0.4042	−0.2245	0.041*
C6	0.60052 (12)	0.33007 (10)	0.0348 (4)	0.0288 (4)
C7	0.52909 (13)	0.32030 (9)	0.1883 (4)	0.0288 (5)
C8	0.54835 (12)	0.26987 (10)	0.3565 (5)	0.0290 (4)
C9	0.67057 (12)	0.19227 (10)	0.4394 (5)	0.0326 (5)
H9A	0.6472	0.1873	0.6041	0.039*
H9B	0.7293	0.2052	0.4568	0.039*
C10	0.66510 (12)	0.12335 (10)	0.3092 (5)	0.0336 (5)
H10A	0.6066	0.1103	0.2890	0.040*
H10B	0.6901	0.1273	0.1464	0.040*
C11	0.70976 (14)	0.06838 (11)	0.4534 (5)	0.0404 (6)
H11A	0.7673	0.0821	0.4774	0.061*
H11B	0.7079	0.0248	0.3647	0.061*
H11C	0.6830	0.0627	0.6112	0.061*
C12	0.49933 (13)	0.24338 (10)	0.5656 (4)	0.0315 (5)
H12A	0.4530	0.2753	0.5963	0.038*
H12B	0.5348	0.2433	0.7115	0.038*
C13	0.46466 (12)	0.17145 (10)	0.5295 (4)	0.0271 (4)
C14	0.47834 (13)	0.12068 (10)	0.7011 (4)	0.0317 (5)
H14	0.5121	0.1302	0.8376	0.038*
C15	0.44300 (14)	0.05585 (11)	0.6750 (5)	0.0360 (5)
H15	0.4527	0.0214	0.7933	0.043*
C16	0.39379 (13)	0.04180 (11)	0.4763 (5)	0.0350 (5)
H16	0.3692	−0.0022	0.4589	0.042*
C17	0.38041 (13)	0.09212 (10)	0.3027 (5)	0.0331 (5)
H17	0.3470	0.0825	0.1656	0.040*
C18	0.41579 (12)	0.15656 (10)	0.3295 (4)	0.0296 (4)
H18	0.4065	0.1908	0.2100	0.036*
C19	0.44951 (13)	0.35436 (10)	0.1705 (4)	0.0308 (5)
C20	0.37460 (14)	0.44182 (11)	−0.0340 (6)	0.0410 (6)
H20A	0.3565	0.4641	0.1180	0.049*
H20B	0.3308	0.4099	−0.0879	0.049*
C21	0.39091 (15)	0.49475 (12)	−0.2251 (5)	0.0442 (6)
H21A	0.4351	0.5254	−0.1710	0.066*
H21B	0.3407	0.5215	−0.2539	0.066*
H21C	0.4076	0.4719	−0.3755	0.066*

	U11	U22	U33	U12	U13	U23
O1	0.0300 (8)	0.0423 (8)	0.0567 (13)	0.0019 (6)	0.0131 (9)	0.0115 (9)
O2	0.0274 (7)	0.0368 (8)	0.0430 (10)	−0.0020 (6)	0.0009 (8)	0.0075 (8)
N1	0.0260 (8)	0.0311 (8)	0.0312 (10)	−0.0032 (6)	0.0012 (8)	−0.0027 (8)
C1	0.0266 (10)	0.0306 (9)	0.0327 (12)	−0.0088 (8)	0.0015 (9)	−0.0073 (9)
C2	0.0254 (10)	0.0386 (10)	0.0426 (14)	−0.0055 (8)	0.0034 (10)	−0.0085 (10)
C3	0.0303 (11)	0.0443 (11)	0.0430 (15)	−0.0113 (9)	0.0102 (11)	−0.0075 (12)
C4	0.0378 (12)	0.0397 (11)	0.0375 (14)	−0.0123 (9)	0.0062 (11)	−0.0025 (11)
C5	0.0336 (11)	0.0316 (9)	0.0365 (12)	−0.0097 (8)	0.0031 (10)	−0.0032 (10)
C6	0.0280 (10)	0.0285 (9)	0.0299 (11)	−0.0067 (7)	0.0022 (9)	−0.0053 (9)
C7	0.0274 (10)	0.0270 (9)	0.0319 (12)	−0.0055 (7)	0.0028 (9)	−0.0027 (9)
C8	0.0268 (10)	0.0302 (9)	0.0299 (11)	−0.0059 (8)	0.0008 (9)	−0.0049 (9)
C9	0.0292 (10)	0.0361 (10)	0.0325 (12)	−0.0017 (8)	−0.0030 (10)	−0.0023 (10)
C10	0.0289 (10)	0.0353 (10)	0.0366 (13)	−0.0010 (8)	−0.0005 (10)	−0.0015 (10)
C11	0.0380 (12)	0.0375 (11)	0.0457 (14)	−0.0001 (9)	−0.0005 (12)	0.0050 (11)
C12	0.0324 (10)	0.0342 (10)	0.0278 (12)	−0.0020 (8)	0.0032 (9)	−0.0037 (9)
C13	0.0231 (9)	0.0308 (9)	0.0273 (11)	0.0012 (7)	0.0046 (8)	−0.0017 (9)
C14	0.0288 (10)	0.0400 (10)	0.0262 (11)	−0.0006 (9)	0.0007 (9)	0.0025 (10)
C15	0.0359 (11)	0.0382 (11)	0.0338 (12)	0.0039 (9)	0.0005 (10)	0.0059 (10)
C16	0.0388 (11)	0.0308 (9)	0.0352 (13)	−0.0024 (8)	0.0057 (10)	−0.0003 (10)
C17	0.0336 (11)	0.0373 (10)	0.0283 (12)	−0.0038 (8)	−0.0018 (10)	−0.0016 (10)
C18	0.0306 (10)	0.0313 (9)	0.0271 (11)	−0.0001 (8)	0.0008 (9)	0.0017 (9)
C19	0.0292 (10)	0.0280 (9)	0.0353 (12)	−0.0052 (8)	0.0025 (10)	−0.0018 (9)
C20	0.0327 (11)	0.0392 (11)	0.0512 (16)	0.0003 (9)	0.0010 (11)	0.0093 (12)
C21	0.0441 (13)	0.0411 (11)	0.0474 (16)	−0.0055 (10)	−0.0029 (12)	0.0099 (12)

O1—C19	1.218 (3)	C10—H10B	0.9900
O2—C19	1.349 (3)	C11—H11A	0.9800
O2—C20	1.446 (3)	C11—H11B	0.9800
N1—C8	1.374 (3)	C11—H11C	0.9800
N1—C1	1.387 (3)	C12—C13	1.523 (3)
N1—C9	1.458 (3)	C12—H12A	0.9900
C1—C2	1.392 (3)	C12—H12B	0.9900
C1—C6	1.412 (3)	C13—C14	1.387 (3)
C2—C3	1.385 (4)	C13—C18	1.391 (3)
C2—H2	0.9500	C14—C15	1.394 (3)
C3—C4	1.398 (3)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.384 (3)
C4—C5	1.378 (3)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.388 (3)
C5—C6	1.404 (3)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.388 (3)
C6—C7	1.449 (3)	C17—H17	0.9500
C7—C8	1.388 (3)	C18—H18	0.9500
C7—C19	1.455 (3)	C20—C21	1.499 (4)
C8—C12	1.494 (3)	C20—H20A	0.9900
C9—C10	1.526 (3)	C20—H20B	0.9900
C9—H9A	0.9900	C21—H21A	0.9800
C9—H9B	0.9900	C21—H21B	0.9800
C10—C11	1.518 (3)	C21—H21C	0.9800
C10—H10A	0.9900
C19—O2—C20	116.62 (17)	C10—C11—H11C	109.5
C8—N1—C1	109.44 (18)	H11A—C11—H11C	109.5
C8—N1—C9	127.0 (2)	H11B—C11—H11C	109.5
C1—N1—C9	123.49 (17)	C8—C12—C13	114.42 (18)
N1—C1—C2	128.7 (2)	C8—C12—H12A	108.7
N1—C1—C6	108.43 (17)	C13—C12—H12A	108.7
C2—C1—C6	122.9 (2)	C8—C12—H12B	108.7
C3—C2—C1	116.8 (2)	C13—C12—H12B	108.7
C3—C2—H2	121.6	H12A—C12—H12B	107.6
C1—C2—H2	121.6	C14—C13—C18	119.03 (18)
C2—C3—C4	121.6 (2)	C14—C13—C12	120.5 (2)
C2—C3—H3	119.2	C18—C13—C12	120.43 (19)
C4—C3—H3	119.2	C13—C14—C15	120.6 (2)
C5—C4—C3	121.4 (2)	C13—C14—H14	119.7
C5—C4—H4	119.3	C15—C14—H14	119.7
C3—C4—H4	119.3	C16—C15—C14	119.9 (2)
C4—C5—C6	118.8 (2)	C16—C15—H15	120.1
C4—C5—H5	120.6	C14—C15—H15	120.1
C6—C5—H5	120.6	C15—C16—C17	119.9 (2)
C5—C6—C1	118.65 (19)	C15—C16—H16	120.1
C5—C6—C7	135.6 (2)	C17—C16—H16	120.1
C1—C6—C7	105.70 (19)	C18—C17—C16	120.0 (2)
C8—C7—C6	107.73 (18)	C18—C17—H17	120.0
C8—C7—C19	124.58 (19)	C16—C17—H17	120.0
C6—C7—C19	127.7 (2)	C17—C18—C13	120.6 (2)
N1—C8—C7	108.7 (2)	C17—C18—H18	119.7
N1—C8—C12	121.3 (2)	C13—C18—H18	119.7
C7—C8—C12	129.92 (19)	O1—C19—O2	121.99 (19)
N1—C9—C10	113.02 (19)	O1—C19—C7	126.6 (2)
N1—C9—H9A	109.0	O2—C19—C7	111.41 (18)
C10—C9—H9A	109.0	O2—C20—C21	106.99 (19)
N1—C9—H9B	109.0	O2—C20—H20A	110.3
C10—C9—H9B	109.0	C21—C20—H20A	110.3
H9A—C9—H9B	107.8	O2—C20—H20B	110.3
C11—C10—C9	110.2 (2)	C21—C20—H20B	110.3
C11—C10—H10A	109.6	H20A—C20—H20B	108.6
C9—C10—H10A	109.6	C20—C21—H21A	109.5
C11—C10—H10B	109.6	C20—C21—H21B	109.5
C9—C10—H10B	109.6	H21A—C21—H21B	109.5
H10A—C10—H10B	108.1	C20—C21—H21C	109.5
C10—C11—H11A	109.5	H21A—C21—H21C	109.5
C10—C11—H11B	109.5	H21B—C21—H21C	109.5
H11A—C11—H11B	109.5
C8—N1—C1—C2	−180.0 (2)	C6—C7—C8—C12	175.6 (2)
C9—N1—C1—C2	−2.4 (3)	C19—C7—C8—C12	−6.3 (4)
C8—N1—C1—C6	0.2 (2)	C8—N1—C9—C10	96.0 (3)
C9—N1—C1—C6	177.74 (19)	C1—N1—C9—C10	−81.1 (2)
N1—C1—C2—C3	−179.6 (2)	N1—C9—C10—C11	−178.64 (18)
C6—C1—C2—C3	0.2 (3)	N1—C8—C12—C13	−75.8 (3)
C1—C2—C3—C4	−0.7 (3)	C7—C8—C12—C13	107.9 (2)
C2—C3—C4—C5	0.6 (4)	C8—C12—C13—C14	127.6 (2)
C3—C4—C5—C6	−0.1 (3)	C8—C12—C13—C18	−55.3 (3)
C4—C5—C6—C1	−0.4 (3)	C18—C13—C14—C15	−0.6 (3)
C4—C5—C6—C7	−179.1 (2)	C12—C13—C14—C15	176.5 (2)
N1—C1—C6—C5	−179.83 (18)	C13—C14—C15—C16	0.0 (3)
C2—C1—C6—C5	0.3 (3)	C14—C15—C16—C17	0.6 (3)
N1—C1—C6—C7	−0.8 (2)	C15—C16—C17—C18	−0.5 (3)
C2—C1—C6—C7	179.4 (2)	C16—C17—C18—C13	−0.1 (3)
C5—C6—C7—C8	179.9 (2)	C14—C13—C18—C17	0.7 (3)
C1—C6—C7—C8	1.1 (2)	C12—C13—C18—C17	−176.49 (19)
C5—C6—C7—C19	1.8 (4)	C20—O2—C19—O1	−0.7 (3)
C1—C6—C7—C19	−177.0 (2)	C20—O2—C19—C7	178.6 (2)
C1—N1—C8—C7	0.5 (2)	C8—C7—C19—O1	−5.9 (4)
C9—N1—C8—C7	−176.92 (19)	C6—C7—C19—O1	171.8 (2)
C1—N1—C8—C12	−176.43 (18)	C8—C7—C19—O2	174.8 (2)
C9—N1—C8—C12	6.1 (3)	C6—C7—C19—O2	−7.5 (3)
C6—C7—C8—N1	−1.0 (2)	C19—O2—C20—C21	−179.8 (2)
C19—C7—C8—N1	177.15 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.95	2.71	3.653 (3)	173
C9—H9B···O1i	0.99	2.88	3.680 (3)	138
C11—H11A···O1i	0.98	2.69	3.514 (3)	142
C12—H12A···O1	0.99	2.39	3.044 (3)	123
C18—H18···O1	0.95	2.96	3.620 (3)	128
C21—H21A···O2ii	0.98	2.91	3.555 (3)	124
C3—H3···Cgiii	0.95	2.82	3.632 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.95	2.71	3.653 (3)	173
C9—H9B⋯O1i	0.99	2.88	3.680 (3)	138
C11—H11A⋯O1i	0.98	2.69	3.514 (3)	142
C12—H12A⋯O1	0.99	2.39	3.044 (3)	123
C18—H18⋯O1	0.95	2.96	3.620 (3)	128
C21—H21A⋯O2ii	0.98	2.91	3.555 (3)	124
C3—H3⋯Cgiii	0.95	2.82	3.632 (3)	144

Symmetry codes: (i) ; (ii) ; (iii) . Cg is the centroid of the C13–C18 ring.