Phen-yl(pyrrolo[2,1-a]isoquinolin-3-yl)methanone.

In the title compound, C(19)H(13)NO, the fused isoquinoline-pyrrole system is planar (r.m.s. deviation = 0.0249] Å) and makes a dihedral angle of 53.73 (9)° with the phenyl ring. An intra-molecular C-H⋯O inter-action generates an S(6) ring motif.

Related literature

For the biological activity of indolizine, see: Olden et al. (1991 ▶); Jaffrezou et al. (1992 ▶). For our work on the direct one-pot syntheses of pyrrolo[2,1-a]isoquinolines, see: Liu et al. (2010 ▶). For the preparation of pyrrolo[2,1-a]isoquinoline, see: Verna et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H13NO

M = 271.30

Monoclinic,

a = 28.637 (6) Å

b = 4.0400 (8) Å

c = 11.824 (2) Å

β = 101.02 (3)°

V = 1342.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995 ▶) T min = 0.976, T max = 0.992

2351 measured reflections

2351 independent reflections

1388 reflections with I > 2σ(I)

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.139

S = 1.00

2351 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017101/ds2027sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017101/ds2027Isup2.hkl

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

C19H13NO	F(000) = 568
Mr = 271.30	Dx = 1.342 Mg m−3
Monoclinic, P21/c	Melting point: 413 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 28.637 (6) Å	Cell parameters from 25 reflections
b = 4.0400 (8) Å	θ = 9–12°
c = 11.824 (2) Å	µ = 0.08 mm−1
β = 101.02 (3)°	T = 295 K
V = 1342.7 (5) Å3	Block, colourless
Z = 4	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1388 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.0000
graphite	θmax = 25.0°, θmin = 1.5°
ω/2θ scans	h = −34→33
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	k = 0→4
Tmin = 0.976, Tmax = 0.992	l = 0→14
2351 measured reflections	3 standard reflections every 200 reflections
2351 independent reflections	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)] = 0.072	H-atom parameters constrained
wR(F2) = 0.139	w = 1/[σ2(Fo2) + (0.015P)2 + 2.250P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2351 reflections	Δρmax = 0.23 e Å−3
190 parameters	Δρmin = −0.29 e Å−3
0 restraints	Absolute structure: (XCAD4; Harms & Wocadlo, 1995)
Primary atom site location: structure-invariant direct methods

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N	0.22455 (9)	0.5534 (7)	0.9319 (2)	0.0382 (7)
C11	0.19331 (11)	0.4146 (9)	0.9955 (3)	0.0402 (9)
C7	0.31218 (12)	0.5686 (10)	0.9370 (3)	0.0485 (10)
O	0.30873 (9)	0.6625 (9)	0.8377 (2)	0.0725 (10)
C12	0.14286 (12)	0.4449 (10)	0.9532 (3)	0.0447 (9)
C3	0.36071 (11)	0.5108 (10)	1.0092 (3)	0.0453 (9)
C8	0.27112 (11)	0.4828 (9)	0.9873 (3)	0.0402 (9)
C19	0.20843 (12)	0.7328 (10)	0.8334 (3)	0.0461 (9)
H19A	0.2302	0.8309	0.7947	0.055*
C18	0.16185 (12)	0.7680 (10)	0.7927 (3)	0.0513 (10)
H18A	0.1517	0.8929	0.7265	0.062*
C2	0.37259 (12)	0.6034 (10)	1.1233 (3)	0.0521 (10)
H2A	0.3496	0.6935	1.1600	0.062*
C17	0.12699 (12)	0.6158 (10)	0.8496 (3)	0.0483 (10)
C9	0.26796 (12)	0.3050 (10)	1.0848 (3)	0.0458 (9)
H9A	0.2936	0.2284	1.1389	0.055*
C10	0.22029 (12)	0.2579 (10)	1.0897 (3)	0.0477 (10)
H10A	0.2086	0.1416	1.1462	0.057*
C13	0.10950 (12)	0.3043 (10)	1.0117 (3)	0.0528 (10)
H13A	0.1197	0.1878	1.0798	0.063*
C14	0.06138 (14)	0.3388 (13)	0.9681 (4)	0.0706 (14)
H14A	0.0393	0.2498	1.0080	0.085*
C16	0.07802 (13)	0.6403 (12)	0.8072 (3)	0.0628 (12)
H16A	0.0672	0.7509	0.7382	0.075*
C6	0.45267 (14)	0.4265 (12)	1.1284 (4)	0.0711 (13)
H6A	0.4837	0.3990	1.1684	0.085*
C15	0.04577 (15)	0.5046 (13)	0.8655 (4)	0.0711 (14)
H15A	0.0134	0.5238	0.8361	0.085*
C4	0.39519 (13)	0.3782 (11)	0.9543 (3)	0.0567 (11)
H4A	0.3875	0.3207	0.8769	0.068*
C5	0.44071 (14)	0.3323 (12)	1.0152 (4)	0.0684 (13)
H5A	0.4635	0.2365	0.9792	0.082*
C1	0.41862 (13)	0.5626 (12)	1.1833 (3)	0.0650 (12)
H1A	0.4267	0.6263	1.2602	0.078*

	U11	U22	U33	U12	U13	U23
N	0.0359 (15)	0.0496 (19)	0.0307 (13)	0.0024 (15)	0.0101 (11)	−0.0003 (15)
C11	0.0396 (19)	0.048 (2)	0.0360 (17)	−0.0023 (18)	0.0148 (15)	−0.0037 (18)
C7	0.046 (2)	0.064 (3)	0.0387 (18)	0.013 (2)	0.0169 (16)	0.007 (2)
O	0.0555 (17)	0.117 (3)	0.0500 (15)	0.0072 (19)	0.0227 (13)	0.0212 (19)
C12	0.0393 (19)	0.050 (2)	0.047 (2)	−0.0018 (19)	0.0148 (16)	−0.013 (2)
C3	0.0328 (18)	0.058 (3)	0.049 (2)	0.0002 (19)	0.0162 (16)	0.007 (2)
C8	0.0398 (19)	0.050 (2)	0.0334 (17)	0.0048 (18)	0.0122 (14)	0.0029 (18)
C19	0.051 (2)	0.057 (3)	0.0318 (17)	0.006 (2)	0.0117 (15)	0.0012 (19)
C18	0.049 (2)	0.064 (3)	0.0399 (19)	0.017 (2)	0.0073 (16)	0.009 (2)
C2	0.043 (2)	0.062 (3)	0.054 (2)	−0.002 (2)	0.0160 (17)	0.000 (2)
C17	0.0379 (19)	0.061 (3)	0.046 (2)	0.008 (2)	0.0071 (15)	−0.010 (2)
C9	0.0394 (19)	0.060 (3)	0.0387 (18)	0.008 (2)	0.0095 (15)	0.0068 (19)
C10	0.045 (2)	0.061 (3)	0.0396 (18)	−0.007 (2)	0.0161 (15)	0.006 (2)
C13	0.046 (2)	0.057 (3)	0.059 (2)	−0.008 (2)	0.0191 (18)	−0.010 (2)
C14	0.041 (2)	0.091 (4)	0.085 (3)	−0.015 (3)	0.026 (2)	−0.028 (3)
C16	0.046 (2)	0.075 (3)	0.064 (2)	0.012 (2)	0.0013 (19)	−0.008 (3)
C6	0.040 (2)	0.082 (4)	0.090 (3)	−0.004 (2)	0.008 (2)	0.022 (3)
C15	0.042 (2)	0.083 (4)	0.086 (3)	0.003 (3)	0.007 (2)	−0.027 (3)
C4	0.046 (2)	0.064 (3)	0.066 (2)	0.003 (2)	0.0244 (19)	−0.002 (2)
C5	0.048 (2)	0.068 (3)	0.097 (3)	0.006 (2)	0.033 (2)	0.005 (3)
C1	0.048 (2)	0.085 (3)	0.060 (2)	−0.012 (3)	0.0059 (19)	0.003 (3)

N—C19	1.374 (4)	C17—C16	1.399 (5)
N—C11	1.392 (4)	C9—C10	1.390 (4)
N—C8	1.399 (4)	C9—H9A	0.9300
C11—C10	1.382 (5)	C10—H10A	0.9300
C11—C12	1.441 (4)	C13—C14	1.383 (5)
C7—O	1.220 (4)	C13—H13A	0.9300
C7—C8	1.458 (4)	C14—C15	1.383 (6)
C7—C3	1.504 (5)	C14—H14A	0.9300
C12—C13	1.402 (5)	C16—C15	1.368 (6)
C12—C17	1.404 (5)	C16—H16A	0.9300
C3—C2	1.379 (5)	C6—C5	1.371 (5)
C3—C4	1.388 (4)	C6—C1	1.385 (5)
C8—C9	1.376 (4)	C6—H6A	0.9300
C19—C18	1.336 (4)	C15—H15A	0.9300
C19—H19A	0.9300	C4—C5	1.376 (5)
C18—C17	1.444 (5)	C4—H4A	0.9300
C18—H18A	0.9300	C5—H5A	0.9300
C2—C1	1.382 (5)	C1—H1A	0.9300
C2—H2A	0.9300
C19—N—C11	121.6 (3)	C8—C9—C10	109.2 (3)
C19—N—C8	129.8 (3)	C8—C9—H9A	125.4
C11—N—C8	108.5 (3)	C10—C9—H9A	125.4
C10—C11—N	107.6 (3)	C11—C10—C9	107.8 (3)
C10—C11—C12	133.4 (3)	C11—C10—H10A	126.1
N—C11—C12	118.9 (3)	C9—C10—H10A	126.1
O—C7—C8	123.0 (3)	C14—C13—C12	120.0 (4)
O—C7—C3	119.4 (3)	C14—C13—H13A	120.0
C8—C7—C3	117.4 (3)	C12—C13—H13A	120.0
C13—C12—C17	119.5 (3)	C13—C14—C15	120.5 (4)
C13—C12—C11	121.8 (3)	C13—C14—H14A	119.7
C17—C12—C11	118.7 (3)	C15—C14—H14A	119.7
C2—C3—C4	119.8 (3)	C15—C16—C17	121.2 (4)
C2—C3—C7	122.8 (3)	C15—C16—H16A	119.4
C4—C3—C7	117.2 (3)	C17—C16—H16A	119.4
C9—C8—N	106.9 (3)	C5—C6—C1	120.1 (4)
C9—C8—C7	130.8 (3)	C5—C6—H6A	119.9
N—C8—C7	122.1 (3)	C1—C6—H6A	119.9
C18—C19—N	120.8 (3)	C16—C15—C14	120.0 (4)
C18—C19—H19A	119.6	C16—C15—H15A	120.0
N—C19—H19A	119.6	C14—C15—H15A	120.0
C19—C18—C17	121.2 (3)	C5—C4—C3	119.7 (4)
C19—C18—H18A	119.4	C5—C4—H4A	120.2
C17—C18—H18A	119.4	C3—C4—H4A	120.2
C3—C2—C1	120.2 (4)	C6—C5—C4	120.5 (4)
C3—C2—H2A	119.9	C6—C5—H5A	119.7
C1—C2—H2A	119.9	C4—C5—H5A	119.7
C16—C17—C12	118.8 (4)	C6—C1—C2	119.6 (4)
C16—C17—C18	122.5 (4)	C6—C1—H1A	120.2
C12—C17—C18	118.6 (3)	C2—C1—H1A	120.2
C19—N—C11—C10	−178.7 (3)	C13—C12—C17—C16	−0.1 (6)
C8—N—C11—C10	−0.2 (4)	C11—C12—C17—C16	178.8 (4)
C19—N—C11—C12	3.5 (5)	C13—C12—C17—C18	178.0 (4)
C8—N—C11—C12	−178.0 (3)	C11—C12—C17—C18	−3.0 (5)
C10—C11—C12—C13	1.4 (7)	C19—C18—C17—C16	−178.2 (4)
N—C11—C12—C13	178.5 (3)	C19—C18—C17—C12	3.8 (6)
C10—C11—C12—C17	−177.5 (4)	N—C8—C9—C10	1.2 (4)
N—C11—C12—C17	−0.4 (5)	C7—C8—C9—C10	−173.2 (4)
O—C7—C3—C2	138.8 (4)	N—C11—C10—C9	0.9 (4)
C8—C7—C3—C2	−46.0 (6)	C12—C11—C10—C9	178.2 (4)
O—C7—C3—C4	−36.8 (6)	C8—C9—C10—C11	−1.3 (5)
C8—C7—C3—C4	138.3 (4)	C17—C12—C13—C14	−1.0 (6)
C19—N—C8—C9	177.8 (3)	C11—C12—C13—C14	−179.9 (4)
C11—N—C8—C9	−0.6 (4)	C12—C13—C14—C15	1.6 (7)
C19—N—C8—C7	−7.2 (6)	C12—C17—C16—C15	0.7 (6)
C11—N—C8—C7	174.4 (3)	C18—C17—C16—C15	−177.3 (4)
O—C7—C8—C9	162.9 (4)	C17—C16—C15—C14	−0.2 (7)
C3—C7—C8—C9	−12.1 (6)	C13—C14—C15—C16	−1.0 (7)
O—C7—C8—N	−10.8 (6)	C2—C3—C4—C5	1.7 (6)
C3—C7—C8—N	174.2 (3)	C7—C3—C4—C5	177.5 (4)
C11—N—C19—C18	−2.9 (5)	C1—C6—C5—C4	1.4 (7)
C8—N—C19—C18	178.9 (4)	C3—C4—C5—C6	−2.2 (7)
N—C19—C18—C17	−0.8 (6)	C5—C6—C1—C2	−0.1 (7)
C4—C3—C2—C1	−0.4 (6)	C3—C2—C1—C6	−0.4 (7)
C7—C3—C2—C1	−175.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···O	0.93	2.31	2.875 (4)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19A⋯O	0.93	2.31	2.875 (4)	119