1-Benzyl-2-(1H-indol-3-yl)-5-oxo-pyrrolidine-2-carbonitrile.

In the title compound, C(20)H(17)N(3)O, a potential anti-human immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse-transcriptase inhibitor, the pyrrolidine ring has an envelope conformation. In the crystal structure, adjacent mol-ecules are connected into infinite chains via an N-H⋯O hydrogen bond.

Related literature

For details of the synthesis, see: Martirosyan et al. (2000 ▶, 2004 ▶). For details of the pharmacological properties of compounds of this family, see: De Clercq (1996 ▶). For the crystal structures of some analogs of the title compound, see: Karapetyan et al. (2002 ▶); Tamazyan et al. (2002 ▶).

Experimental

Crystal data

C20H17N3O

M = 315.37

Triclinic,

a = 7.5781 (15) Å

b = 9.4521 (19) Å

c = 12.409 (3) Å

α = 78.02 (3)°

β = 83.05 (3)°

γ = 69.68 (3)°

V = 814.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.4 × 0.3 × 0.2 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

9470 measured reflections

4735 independent reflections

3450 reflections with I > 2σ(I)

R int = 0.020

3 standard reflections frequency: 180 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.130

S = 1.02

4735 reflections

285 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CAD-4 Manual (Enraf–Nonius, 1988 ▶); cell refinement: CAD-4 Manual; data reduction: HELENA (Spek, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker 2000 ▶) and ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067670/su2039sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067670/su2039Isup2.hkl

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

C20H17N3O	Z = 2
Mr = 315.37	F000 = 332
Triclinic, P1	Dx = 1.286 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.5781 (15) Å	Cell parameters from 22 reflections
b = 9.4521 (19) Å	θ = 14.2–17.5º
c = 12.409 (3) Å	µ = 0.08 mm−1
α = 78.02 (3)º	T = 293 (2) K
β = 83.05 (3)º	Prism, colourless
γ = 69.68 (3)º	0.4 × 0.3 × 0.2 mm
V = 814.2 (3) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.020
Radiation source: fine-focus sealed tube	θmax = 30.0º
Monochromator: graphite	θmin = 1.7º
T = 293(2) K	h = −10→10
θ/2θ scans	k = −13→13
Absorption correction: none	l = −17→17
9470 measured reflections	3 standard reflections
4735 independent reflections	every 180 min
3450 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0649P)2 + 0.0907P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
4735 reflections	Δρmax = 0.18 e Å−3
285 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N1	0.22574 (14)	0.71961 (10)	0.23198 (8)	0.0367 (2)
C2	0.20774 (17)	0.64700 (12)	0.14116 (9)	0.0385 (2)
C3	0.3119 (3)	0.72278 (16)	0.04282 (12)	0.0552 (4)
H3A	0.448 (3)	0.655 (2)	0.0402 (14)	0.066 (5)*
H3B	0.258 (2)	0.728 (2)	−0.0253 (16)	0.069 (5)*
C4	0.2913 (3)	0.87637 (17)	0.07212 (14)	0.0642 (4)
H4A	0.182 (3)	0.955 (3)	0.0430 (19)	0.096 (7)*
H4B	0.408 (3)	0.908 (3)	0.049 (2)	0.102 (7)*
C5	0.26566 (17)	0.85107 (13)	0.19576 (12)	0.0453 (3)
O6	0.27772 (15)	0.93414 (11)	0.25649 (10)	0.0628 (3)
C7	0.0051 (2)	0.69595 (15)	0.11645 (11)	0.0503 (3)
N8	−0.1486 (2)	0.73626 (18)	0.09409 (14)	0.0761 (4)
C9	0.28897 (17)	0.47561 (12)	0.16540 (9)	0.0379 (2)
C10	0.2034 (2)	0.37431 (15)	0.15315 (11)	0.0480 (3)
H10	0.076 (2)	0.3968 (19)	0.1273 (14)	0.063 (5)*
H11	0.298 (3)	0.140 (2)	0.1869 (15)	0.073 (5)*
N11	0.32401 (19)	0.22756 (13)	0.18058 (10)	0.0543 (3)
C12	0.48874 (19)	0.23143 (13)	0.21285 (10)	0.0435 (3)
C13	0.6498 (2)	0.11135 (15)	0.24876 (12)	0.0574 (4)
H13	0.655 (2)	0.009 (2)	0.2546 (15)	0.068 (5)*
C14	0.7955 (2)	0.14884 (19)	0.27645 (14)	0.0656 (4)
H14	0.911 (3)	0.066 (2)	0.3034 (16)	0.079 (5)*
C15	0.7826 (2)	0.30164 (19)	0.26931 (15)	0.0641 (4)
H15	0.887 (3)	0.324 (2)	0.2894 (16)	0.078 (5)*
C16	0.62465 (19)	0.42094 (15)	0.23300 (12)	0.0498 (3)
H16	0.620 (2)	0.5269 (19)	0.2264 (14)	0.059 (4)*
C17	0.47300 (17)	0.38670 (12)	0.20376 (9)	0.0379 (2)
C18	0.20486 (17)	0.65739 (14)	0.34923 (10)	0.0395 (2)
H18A	0.258 (2)	0.5459 (17)	0.3571 (12)	0.047 (4)*
H18B	0.280 (2)	0.6986 (17)	0.3851 (13)	0.054 (4)*
C19	0.00691 (16)	0.70242 (13)	0.40041 (9)	0.0376 (2)
C20	−0.1177 (2)	0.63319 (19)	0.38244 (12)	0.0545 (3)
H20	−0.077 (2)	0.557 (2)	0.3324 (15)	0.070 (5)*
C21	−0.2973 (2)	0.6704 (3)	0.43232 (14)	0.0744 (5)
H21	−0.385 (3)	0.624 (2)	0.4196 (19)	0.098 (7)*
C22	−0.3538 (3)	0.7749 (2)	0.50150 (15)	0.0782 (6)
H22	−0.484 (3)	0.800 (2)	0.5378 (19)	0.099 (7)*
C23	−0.2317 (3)	0.8426 (2)	0.52187 (14)	0.0750 (5)
H23	−0.264 (3)	0.914 (3)	0.5704 (19)	0.095 (7)*
C24	−0.0502 (2)	0.80719 (16)	0.47138 (11)	0.0542 (3)
H24	0.038 (2)	0.858 (2)	0.4834 (14)	0.065 (5)*

	U11	U22	U33	U12	U13	U23
N1	0.0439 (5)	0.0279 (4)	0.0399 (5)	−0.0152 (4)	0.0056 (4)	−0.0083 (3)
C2	0.0494 (6)	0.0315 (5)	0.0350 (5)	−0.0157 (5)	0.0037 (5)	−0.0062 (4)
C3	0.0742 (10)	0.0429 (7)	0.0425 (7)	−0.0210 (7)	0.0150 (7)	−0.0026 (5)
C4	0.0842 (11)	0.0384 (7)	0.0649 (9)	−0.0266 (7)	0.0159 (8)	0.0017 (6)
C5	0.0426 (6)	0.0272 (5)	0.0655 (8)	−0.0132 (4)	0.0051 (5)	−0.0089 (5)
O6	0.0691 (7)	0.0387 (5)	0.0905 (8)	−0.0253 (5)	0.0011 (6)	−0.0228 (5)
C7	0.0609 (8)	0.0433 (6)	0.0447 (7)	−0.0147 (6)	−0.0096 (6)	−0.0040 (5)
N8	0.0693 (9)	0.0762 (10)	0.0782 (10)	−0.0154 (7)	−0.0267 (8)	−0.0059 (8)
C9	0.0500 (6)	0.0304 (5)	0.0358 (5)	−0.0170 (5)	0.0045 (5)	−0.0089 (4)
C10	0.0624 (8)	0.0415 (6)	0.0490 (7)	−0.0263 (6)	−0.0024 (6)	−0.0121 (5)
N11	0.0788 (8)	0.0341 (5)	0.0594 (7)	−0.0295 (5)	0.0002 (6)	−0.0122 (5)
C12	0.0605 (7)	0.0309 (5)	0.0390 (6)	−0.0180 (5)	0.0111 (5)	−0.0089 (4)
C13	0.0738 (10)	0.0326 (6)	0.0532 (8)	−0.0100 (6)	0.0146 (7)	−0.0041 (5)
C14	0.0545 (9)	0.0536 (8)	0.0666 (10)	−0.0005 (7)	0.0081 (7)	0.0005 (7)
C15	0.0467 (8)	0.0635 (9)	0.0771 (11)	−0.0168 (7)	0.0016 (7)	−0.0070 (8)
C16	0.0471 (7)	0.0418 (6)	0.0622 (8)	−0.0188 (5)	0.0056 (6)	−0.0105 (6)
C17	0.0475 (6)	0.0299 (5)	0.0369 (5)	−0.0156 (4)	0.0097 (5)	−0.0095 (4)
C18	0.0411 (6)	0.0387 (6)	0.0377 (6)	−0.0114 (5)	−0.0004 (5)	−0.0090 (4)
C19	0.0429 (6)	0.0351 (5)	0.0307 (5)	−0.0093 (4)	0.0006 (4)	−0.0049 (4)
C20	0.0553 (8)	0.0719 (9)	0.0436 (7)	−0.0304 (7)	0.0050 (6)	−0.0144 (6)
C21	0.0521 (9)	0.1182 (16)	0.0534 (9)	−0.0380 (10)	0.0035 (7)	−0.0031 (9)
C22	0.0529 (9)	0.0940 (13)	0.0560 (9)	−0.0023 (9)	0.0154 (7)	0.0060 (9)
C23	0.0899 (13)	0.0588 (9)	0.0509 (8)	0.0010 (9)	0.0230 (8)	−0.0149 (7)
C24	0.0726 (9)	0.0435 (7)	0.0429 (7)	−0.0147 (6)	0.0073 (6)	−0.0138 (5)

N1—C5	1.3542 (15)	C13—C14	1.370 (3)
N1—C18	1.4634 (16)	C13—H13	0.944 (18)
N1—C2	1.4775 (15)	C14—C15	1.398 (2)
C2—C7	1.493 (2)	C14—H14	0.99 (2)
C2—C9	1.4979 (16)	C15—C16	1.375 (2)
C2—C3	1.5562 (18)	C15—H15	0.96 (2)
C3—C4	1.521 (2)	C16—C17	1.4018 (18)
C3—H3A	1.009 (18)	C16—H16	0.976 (16)
C3—H3B	0.969 (18)	C18—C19	1.5076 (17)
C4—C5	1.502 (2)	C18—H18A	0.977 (15)
C4—H4A	0.95 (2)	C18—H18B	0.983 (16)
C4—H4B	1.02 (2)	C19—C20	1.3824 (19)
C5—O6	1.2269 (16)	C19—C24	1.3842 (17)
C7—N8	1.142 (2)	C20—C21	1.383 (2)
C9—C10	1.3695 (17)	C20—H20	0.989 (18)
C9—C17	1.4348 (18)	C21—C22	1.366 (3)
C10—N11	1.3689 (19)	C21—H21	0.95 (2)
C10—H10	0.994 (17)	C22—C23	1.365 (3)
N11—C12	1.3707 (19)	C22—H22	1.00 (2)
N11—H11	0.90 (2)	C23—C24	1.399 (2)
C12—C13	1.391 (2)	C23—H23	0.94 (2)
C12—C17	1.4120 (15)	C24—H24	0.986 (17)
C5—N1—C18	122.70 (10)	C14—C13—H13	122.7 (10)
C5—N1—C2	112.91 (10)	C12—C13—H13	120.0 (10)
C18—N1—C2	124.39 (9)	C13—C14—C15	121.35 (15)
N1—C2—C7	109.37 (10)	C13—C14—H14	119.6 (11)
N1—C2—C9	113.04 (10)	C15—C14—H14	119.1 (11)
C7—C2—C9	110.17 (11)	C16—C15—C14	121.65 (16)
N1—C2—C3	101.87 (10)	C16—C15—H15	118.9 (11)
C7—C2—C3	108.24 (12)	C14—C15—H15	119.4 (11)
C9—C2—C3	113.77 (10)	C15—C16—C17	118.50 (13)
C4—C3—C2	104.09 (11)	C15—C16—H16	120.4 (9)
C4—C3—H3A	111.4 (10)	C17—C16—H16	121.1 (9)
C2—C3—H3A	107.7 (10)	C16—C17—C12	118.72 (12)
C4—C3—H3B	115.6 (11)	C16—C17—C9	134.95 (11)
C2—C3—H3B	109.1 (11)	C12—C17—C9	106.31 (11)
H3A—C3—H3B	108.5 (14)	N1—C18—C19	116.05 (10)
C5—C4—C3	104.26 (11)	N1—C18—H18A	106.8 (9)
C5—C4—H4A	108.1 (14)	C19—C18—H18A	109.9 (8)
C3—C4—H4A	112.0 (13)	N1—C18—H18B	103.9 (9)
C5—C4—H4B	109.1 (14)	C19—C18—H18B	108.7 (9)
C3—C4—H4B	112.6 (13)	H18A—C18—H18B	111.5 (12)
H4A—C4—H4B	110.6 (19)	C20—C19—C24	118.62 (13)
O6—C5—N1	124.06 (13)	C20—C19—C18	120.58 (11)
O6—C5—C4	126.73 (12)	C24—C19—C18	120.70 (12)
N1—C5—C4	109.21 (11)	C19—C20—C21	120.72 (15)
N8—C7—C2	177.60 (16)	C19—C20—H20	118.9 (10)
C10—C9—C17	107.09 (11)	C21—C20—H20	120.3 (10)
C10—C9—C2	126.59 (12)	C22—C21—C20	120.49 (18)
C17—C9—C2	126.31 (10)	C22—C21—H21	118.2 (14)
N11—C10—C9	109.47 (13)	C20—C21—H21	121.3 (14)
N11—C10—H10	122.1 (10)	C23—C22—C21	119.72 (16)
C9—C10—H10	128.4 (10)	C23—C22—H22	120.8 (12)
C10—N11—C12	109.29 (11)	C21—C22—H22	119.5 (12)
C10—N11—H11	127.3 (11)	C22—C23—C24	120.51 (16)
C12—N11—H11	122.9 (11)	C22—C23—H23	122.7 (14)
N11—C12—C13	129.75 (12)	C24—C23—H23	116.8 (14)
N11—C12—C17	107.83 (12)	C19—C24—C23	119.93 (17)
C13—C12—C17	122.42 (14)	C19—C24—H24	118.7 (10)
C14—C13—C12	117.34 (13)	C23—C24—H24	121.3 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O6i	0.90 (2)	2.01 (2)	2.866 (2)	158 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11⋯O6i	0.90 (2)	2.01 (2)	2.866 (2)	158 (2)

Symmetry code: (i) .