(E)-3-[4-(Dimethyl-amino)-benzyl-idene]-2,3-di-hydro-1H,9H-pyrrolo-[2,1-b]quinazolin-9-one.

The title compound, C(20)H(19)N(3)O, was obtained by condensation of 2,3-dihydro-1H,9H-pyrrolo-[2,1-b]quinazolin-9-one (alkaloid de-oxy-vasicinone, isolated from Peganum Harmala) with 4-(dimethyl-amino)-benzaldehyde in the presence of sodium methoxide. The 2,3-dihydro-1H,9H-pyrrolo-[2,1-b]quinazolin-9-one part of the mol-ecule is roughly planar (r.m.s. deviation = 0.0178 Å) and is essentially coplanar with the benzil-idene ring (r.m.s. deviation = 0.0080 Å), forming a dihedral angle of 5.0 (1)°. The crystal structure is stabilized by two aromatic π-π stacking inter-actions observed between the benzene rings of neighboring mol-ecules [centroid-centroid distance = 3.7555 (19) Å.

Related literature

For the synthesis of 2,3-dihydro-1H-pyrrolo­[2,1-b]quinazolin-9-one and the title compound, see: Shakhidoyatov et al. (1977 ▶); Elmuradov et al. (2009 ▶); Shakhidoyatov & Kaysarov, (1998 ▶); Jahng et al. (2008 ▶). For the physiological activity of 2,3-dihydro-1H-pyrrolo­[2,1-b]quinazolin-9-one and its derivatives, see: Chatterjee & Ganguly, (1968 ▶); Al-Shamma et al. (1981 ▶); Johne (1981 ▶); Telezhenetskaya & Yunusov, (1977 ▶); Yunusov et al. (1978 ▶). For related structures, see: Barnes et al. (1985 ▶); Wu et al. (1997 ▶).

Experimental

Crystal data

C20H19N3O

M = 317.38

Monoclinic,

a = 8.8030 (18) Å

b = 16.415 (3) Å

c = 11.463 (2) Å

β = 105.05 (3)°

V = 1599.6 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.66 mm−1

T = 300 K

0.60 × 0.20 × 0.15 mm

Data collection

Stoe Stadi-4 four-circle diffractometer

Absorption correction: ψ scan (X-RED; Stoe & Cie, 1997 ▶). T min = 0.854, T max = 0.906

2446 measured reflections

2342 independent reflections

1728 reflections with I > 2σ(I)

θmax = 60.0°

3 standard reflections every 60 min intensity decay: 10.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.142

S = 1.13

2342 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: STADI4 (Stoe & Cie, 1997 ▶); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810020878/si2264sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020878/si2264Isup2.hkl

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

C20H19N3O	F(000) = 672
Mr = 317.38	Dx = 1.318 Mg m−3
Monoclinic, P21/c	Melting point: 514(2) K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 8.8030 (18) Å	Cell parameters from 12 reflections
b = 16.415 (3) Å	θ = 10–20°
c = 11.463 (2) Å	µ = 0.66 mm−1
β = 105.05 (3)°	T = 300 K
V = 1599.6 (6) Å3	Prizmatic, light yellow
Z = 4	0.60 × 0.20 × 0.15 mm

Stoe Stadi-4 four-circle diffractometer	1728 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.0000
graphite	θmax = 60.0°, θmin = 4.8°
Scan width (ω) = 1.32 – 1.56, scan ratio 2θ:ω = 0.00 I(Net) and sigma(I) calculated according to Blessing (1987)	h = −9→9
Absorption correction: ψ scan (X-RED; Stoe & Cie, 1997).	k = 0→18
Tmin = 0.854, Tmax = 0.906	l = 0→12
2446 measured reflections	3 standard reflections every 60 min
2342 independent reflections	intensity decay: 10.0%

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0446P)2 + 1.0639P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
2342 reflections	Δρmax = 0.16 e Å−3
220 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (3)

Experimental. Empirical absorption correction using ψ Scan. Reflections used Mu * R = 0.00 H K L, θ, χ, I~min~/I~max~: -2 1 1 21.1 80.5 0.900

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	−0.1964 (3)	0.57316 (13)	0.07780 (19)	0.0553 (7)
C1	0.0365 (4)	0.48250 (18)	0.2373 (3)	0.0496 (9)
H1A	0.0818	0.4880	0.1691	0.060*
H1B	−0.0432	0.4402	0.2197	0.060*
C2	0.1634 (4)	0.46318 (18)	0.3530 (3)	0.0435 (8)
H2A	0.1435	0.4107	0.3851	0.052*
H2B	0.2663	0.4617	0.3370	0.052*
C3	0.1562 (3)	0.52982 (17)	0.4410 (3)	0.0373 (7)
C3A	0.0343 (3)	0.58741 (17)	0.3798 (2)	0.0355 (7)
N4	−0.0078 (3)	0.65349 (14)	0.4246 (2)	0.0391 (6)
C4A	−0.1278 (3)	0.69758 (17)	0.3470 (3)	0.0378 (7)
C5	−0.1799 (4)	0.76888 (18)	0.3914 (3)	0.0459 (8)
H5A	−0.1330	0.7856	0.4700	0.055*
C6	−0.2995 (4)	0.8144 (2)	0.3201 (3)	0.0495 (8)
H6A	−0.3327	0.8618	0.3503	0.059*
C7	−0.3707 (4)	0.78958 (19)	0.2026 (3)	0.0476 (8)
H7A	−0.4525	0.8201	0.1549	0.057*
C8	−0.3213 (3)	0.72058 (19)	0.1568 (3)	0.0452 (8)
H8A	−0.3690	0.7047	0.0780	0.054*
C8A	−0.1995 (3)	0.67373 (17)	0.2279 (3)	0.0379 (7)
C9	−0.1474 (3)	0.59996 (18)	0.1804 (3)	0.0413 (7)
N10	−0.0298 (3)	0.55973 (14)	0.2639 (2)	0.0384 (6)
N1'	0.7209 (3)	0.34893 (18)	0.8577 (2)	0.0585 (8)
C1'	0.3643 (3)	0.49063 (17)	0.6292 (2)	0.0375 (7)
C2'	0.4284 (4)	0.42189 (18)	0.5885 (3)	0.0445 (8)
H2'A	0.3902	0.4064	0.5081	0.053*
C3'	0.5455 (4)	0.37605 (19)	0.6621 (3)	0.0451 (8)
H3'A	0.5847	0.3310	0.6303	0.054*
C4'	0.6065 (3)	0.39601 (18)	0.7836 (3)	0.0426 (8)
C5'	0.5453 (4)	0.46547 (19)	0.8262 (3)	0.0462 (8)
H5'A	0.5839	0.4812	0.9064	0.055*
C6'	0.4282 (3)	0.51068 (18)	0.7500 (3)	0.0423 (8)
H6'A	0.3904	0.5566	0.7808	0.051*
C7'	0.2395 (3)	0.54038 (17)	0.5554 (3)	0.0383 (7)
H7'A	0.2135	0.5864	0.5934	0.046*
C8'	0.7668 (5)	0.3632 (3)	0.9855 (3)	0.0906 (15)
H8'A	0.6753	0.3623	1.0164	0.136*
H8'B	0.8171	0.4154	1.0015	0.136*
H8'C	0.8386	0.3214	1.0243	0.136*
C9'	0.7788 (4)	0.2766 (2)	0.8122 (3)	0.0617 (10)
H9'A	0.8256	0.2912	0.7482	0.093*
H9'B	0.6932	0.2397	0.7818	0.093*
H9'C	0.8562	0.2509	0.8762	0.093*

	U11	U22	U33	U12	U13	U23
O1	0.0632 (15)	0.0588 (14)	0.0371 (13)	0.0057 (12)	0.0006 (11)	−0.0039 (11)
C1	0.056 (2)	0.0412 (18)	0.0468 (19)	0.0081 (16)	0.0043 (16)	−0.0075 (15)
C2	0.0460 (18)	0.0406 (18)	0.0415 (17)	0.0033 (15)	0.0072 (15)	−0.0009 (14)
C3	0.0345 (16)	0.0388 (16)	0.0379 (16)	−0.0011 (13)	0.0079 (13)	0.0008 (13)
C3A	0.0346 (16)	0.0360 (16)	0.0353 (15)	−0.0039 (13)	0.0079 (13)	−0.0016 (13)
N4	0.0348 (14)	0.0373 (14)	0.0418 (14)	0.0027 (11)	0.0039 (11)	−0.0016 (11)
C4A	0.0363 (17)	0.0348 (16)	0.0427 (17)	−0.0020 (13)	0.0111 (14)	0.0033 (13)
C5	0.0415 (18)	0.0440 (19)	0.0507 (19)	0.0007 (15)	0.0093 (15)	−0.0026 (15)
C6	0.0465 (19)	0.0432 (18)	0.059 (2)	0.0066 (15)	0.0149 (17)	0.0039 (16)
C7	0.0395 (18)	0.0464 (19)	0.057 (2)	0.0056 (15)	0.0124 (15)	0.0178 (16)
C8	0.0378 (17)	0.0506 (19)	0.0455 (18)	0.0015 (15)	0.0079 (14)	0.0109 (15)
C8A	0.0375 (17)	0.0371 (17)	0.0384 (16)	−0.0026 (13)	0.0088 (13)	0.0044 (13)
C9	0.0400 (18)	0.0453 (18)	0.0370 (17)	−0.0056 (14)	0.0072 (14)	0.0017 (14)
N10	0.0401 (14)	0.0368 (14)	0.0356 (13)	0.0023 (11)	0.0051 (11)	−0.0017 (11)
N1'	0.0514 (17)	0.0607 (19)	0.0523 (17)	0.0112 (15)	−0.0062 (14)	0.0008 (14)
C1'	0.0340 (16)	0.0379 (17)	0.0383 (16)	−0.0034 (13)	0.0052 (13)	−0.0011 (13)
C2'	0.0471 (19)	0.0445 (18)	0.0385 (17)	−0.0001 (15)	0.0054 (14)	−0.0029 (14)
C3'	0.0454 (19)	0.0449 (18)	0.0431 (18)	0.0035 (15)	0.0082 (15)	0.0014 (15)
C4'	0.0336 (17)	0.0441 (18)	0.0462 (18)	−0.0052 (14)	0.0033 (14)	0.0058 (15)
C5'	0.0423 (18)	0.0491 (19)	0.0414 (18)	−0.0042 (16)	0.0004 (15)	−0.0028 (15)
C6'	0.0411 (17)	0.0412 (17)	0.0426 (17)	−0.0020 (14)	0.0071 (14)	−0.0046 (14)
C7'	0.0347 (16)	0.0368 (16)	0.0430 (17)	0.0010 (13)	0.0096 (14)	−0.0007 (13)
C8'	0.092 (3)	0.103 (3)	0.056 (2)	0.034 (3)	−0.017 (2)	0.000 (2)
C9'	0.048 (2)	0.055 (2)	0.075 (2)	0.0088 (18)	0.0019 (18)	0.0083 (19)

O1—C9	1.225 (3)	C8A—C9	1.450 (4)
C1—N10	1.461 (4)	C9—N10	1.382 (4)
C1—C2	1.529 (4)	N1'—C4'	1.375 (4)
C1—H1A	0.9700	N1'—C8'	1.434 (4)
C1—H1B	0.9700	N1'—C9'	1.442 (4)
C2—C3	1.500 (4)	C1'—C6'	1.392 (4)
C2—H2A	0.9700	C1'—C2'	1.395 (4)
C2—H2B	0.9700	C1'—C7'	1.452 (4)
C3—C7'	1.338 (4)	C2'—C3'	1.374 (4)
C3—C3A	1.465 (4)	C2'—H2'A	0.9300
C3A—N4	1.295 (3)	C3'—C4'	1.395 (4)
C3A—N10	1.378 (3)	C3'—H3'A	0.9300
N4—C4A	1.394 (4)	C4'—C5'	1.402 (4)
C4A—C5	1.400 (4)	C5'—C6'	1.381 (4)
C4A—C8A	1.403 (4)	C5'—H5'A	0.9300
C5—C6	1.374 (4)	C6'—H6'A	0.9300
C5—H5A	0.9300	C7'—H7'A	0.9300
C6—C7	1.390 (4)	C8'—H8'A	0.9600
C6—H6A	0.9300	C8'—H8'B	0.9600
C7—C8	1.366 (4)	C8'—H8'C	0.9600
C7—H7A	0.9300	C9'—H9'A	0.9600
C8—C8A	1.397 (4)	C9'—H9'B	0.9600
C8—H8A	0.9300	C9'—H9'C	0.9600
N10—C1—C2	103.9 (2)	C3A—N10—C9	123.8 (2)
N10—C1—H1A	111.0	C3A—N10—C1	113.7 (2)
C2—C1—H1A	111.0	C9—N10—C1	122.5 (2)
N10—C1—H1B	111.0	C4'—N1'—C8'	120.5 (3)
C2—C1—H1B	111.0	C4'—N1'—C9'	120.7 (3)
H1A—C1—H1B	109.0	C8'—N1'—C9'	118.2 (3)
C3—C2—C1	106.4 (2)	C6'—C1'—C2'	115.5 (3)
C3—C2—H2A	110.4	C6'—C1'—C7'	119.7 (3)
C1—C2—H2A	110.4	C2'—C1'—C7'	124.8 (3)
C3—C2—H2B	110.4	C3'—C2'—C1'	122.8 (3)
C1—C2—H2B	110.4	C3'—C2'—H2'A	118.6
H2A—C2—H2B	108.6	C1'—C2'—H2'A	118.6
C7'—C3—C3A	122.2 (3)	C2'—C3'—C4'	121.1 (3)
C7'—C3—C2	130.2 (3)	C2'—C3'—H3'A	119.4
C3A—C3—C2	107.6 (2)	C4'—C3'—H3'A	119.4
N4—C3A—N10	124.8 (3)	N1'—C4'—C3'	121.0 (3)
N4—C3A—C3	126.9 (3)	N1'—C4'—C5'	121.8 (3)
N10—C3A—C3	108.3 (2)	C3'—C4'—C5'	117.1 (3)
C3A—N4—C4A	115.4 (2)	C6'—C5'—C4'	120.5 (3)
N4—C4A—C5	117.9 (3)	C6'—C5'—H5'A	119.8
N4—C4A—C8A	123.4 (3)	C4'—C5'—H5'A	119.8
C5—C4A—C8A	118.7 (3)	C5'—C6'—C1'	123.0 (3)
C6—C5—C4A	120.7 (3)	C5'—C6'—H6'A	118.5
C6—C5—H5A	119.6	C1'—C6'—H6'A	118.5
C4A—C5—H5A	119.6	C3—C7'—C1'	129.6 (3)
C5—C6—C7	120.0 (3)	C3—C7'—H7'A	115.2
C5—C6—H6A	120.0	C1'—C7'—H7'A	115.2
C7—C6—H6A	120.0	N1'—C8'—H8'A	109.5
C8—C7—C6	120.4 (3)	N1'—C8'—H8'B	109.5
C8—C7—H7A	119.8	H8'A—C8'—H8'B	109.5
C6—C7—H7A	119.8	N1'—C8'—H8'C	109.5
C7—C8—C8A	120.3 (3)	H8'A—C8'—H8'C	109.5
C7—C8—H8A	119.8	H8'B—C8'—H8'C	109.5
C8A—C8—H8A	119.8	N1'—C9'—H9'A	109.5
C8—C8A—C4A	119.8 (3)	N1'—C9'—H9'B	109.5
C8—C8A—C9	120.7 (3)	H9'A—C9'—H9'B	109.5
C4A—C8A—C9	119.5 (3)	N1'—C9'—H9'C	109.5
O1—C9—N10	120.5 (3)	H9'A—C9'—H9'C	109.5
O1—C9—C8A	126.4 (3)	H9'B—C9'—H9'C	109.5
N10—C9—C8A	113.1 (3)