6-Benzyl-3,4-dimeth-oxy-10-methyl-pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-one.

Pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-ones such as the title compound, C(24)H(21)N(3)O(3), can be obtained in a few minutes in a microwave-assisted three-component reaction from 2-amino-pyridines, isocyanides and 2-carboxy-benz-aldehydes. In the title compound, the pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-one ring system is almost planar (mean deviation 0.068 Å). The dihedral angle between the benzyl ring and the pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-one ring system is 78.2°. The crystal structure is stabilized by inter-molecular C-H⋯O and C-H⋯N hydrogen bonds.

Related literature

For the biological activity of fused imidazo[1,2-a]heterocycles, see: Almirante et al. (1965 ▶); Gueiffier et al. (1998 ▶); Sanfilippo et al. (1988 ▶); Varma & Kumar (1999 ▶). This heterocyclic structure element is present in drugs such as alpidem (anxiolytic), zolpidem (hypnotic) and zolimidine (anti­ulcer), see: Meng et al. (2007 ▶). For the synthesis of pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-ones by the microwave-assisted three-component reaction of 2-amino­pyridines, isocyanides and 2-carboxy­benzaldehydes, see: Mert-Balci et al. (2008 ▶).

Experimental

Crystal data

C24H21N3O3

M = 399.44

Monoclinic,

a = 8.3650 (17) Å

b = 7.0500 (14) Å

c = 15.983 (3) Å

β = 92.27 (3)°

V = 941.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.35 × 0.20 × 0.20 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.965, T max = 0.981

16260 measured reflections

4479 independent reflections

4383 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.080

S = 1.06

4479 reflections

274 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1895 Friedel pairs

Flack parameter: 0.2 (6)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035806/lx2108sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035806/lx2108Isup2.hkl

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

C24H21N3O3	F(000) = 420
Mr = 399.44	Dx = 1.408 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6111 reflections
a = 8.3650 (17) Å	θ = 2.7–28.4°
b = 7.0500 (14) Å	µ = 0.10 mm−1
c = 15.983 (3) Å	T = 100 K
β = 92.27 (3)°	Block, orange
V = 941.8 (3) Å3	0.35 × 0.20 × 0.20 mm
Z = 2

Bruker APEXII diffractometer	4479 independent reflections
Radiation source: fine-focus sealed tube	4383 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 8.3333 pixels mm-1	θmax = 28.5°, θmin = 2.4°
ω scans	h = −10→11
Absorption correction: multi-scan (SADABS; Bruker, 2006)	k = −9→9
Tmin = 0.965, Tmax = 0.981	l = −21→21
16260 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.080	w = 1/[σ2(Fo2) + (0.0521P)2 + 0.1311P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
4479 reflections	Δρmax = 0.23 e Å−3
274 parameters	Δρmin = −0.20 e Å−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.2 (6)

Experimental. Intensities were measured with a Bruker APEX II area detector

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	0.10209 (10)	−0.19983 (13)	0.60571 (5)	0.02146 (17)
O2	0.00203 (10)	−0.51480 (13)	0.68116 (5)	0.02068 (17)
O3	−0.16121 (10)	−0.64479 (12)	0.80584 (5)	0.02256 (18)
N1	0.16148 (11)	0.18429 (14)	0.89977 (6)	0.0188 (2)
N2	0.28372 (11)	0.29948 (15)	0.78537 (6)	0.01719 (18)
N3	0.19436 (11)	0.04583 (14)	0.68445 (5)	0.01692 (19)
C1	0.11724 (12)	−0.12940 (17)	0.67556 (7)	0.0167 (2)
C2	0.05157 (13)	−0.21455 (17)	0.75221 (6)	0.0163 (2)
C3	−0.01653 (12)	−0.39733 (17)	0.74838 (6)	0.0174 (2)
C4	−0.09563 (13)	−0.46934 (17)	0.81773 (7)	0.0187 (2)
C5	−0.10004 (13)	−0.36386 (18)	0.89150 (7)	0.0196 (2)
H5A	−0.1545	−0.4124	0.9379	0.024*
C6	−0.02551 (13)	−0.18914 (17)	0.89725 (7)	0.0186 (2)
H6A	−0.0260	−0.1206	0.9484	0.022*
C7	0.05077 (12)	−0.11180 (17)	0.82860 (7)	0.0163 (2)
C8	0.13440 (12)	0.06634 (16)	0.83200 (6)	0.0167 (2)
C9	0.24986 (13)	0.32389 (17)	0.87093 (7)	0.0181 (2)
C10	0.31098 (13)	0.48761 (18)	0.91234 (7)	0.0197 (2)
H10A	0.2867	0.5093	0.9691	0.024*
C11	0.40443 (13)	0.61520 (17)	0.87209 (7)	0.0210 (2)
C12	0.44105 (14)	0.57844 (18)	0.78680 (8)	0.0221 (2)
H12A	0.5087	0.6638	0.7588	0.027*
C13	0.38171 (14)	0.42520 (17)	0.74504 (7)	0.0202 (2)
H13A	0.4072	0.4041	0.6884	0.024*
C14	0.20519 (13)	0.13373 (16)	0.76184 (7)	0.0169 (2)
C15	0.25250 (13)	0.13309 (17)	0.60803 (6)	0.0176 (2)
H15A	0.2373	0.2721	0.6112	0.021*
H15B	0.1874	0.0860	0.5593	0.021*
C16	0.42737 (13)	0.09168 (16)	0.59426 (7)	0.0168 (2)
C17	0.48763 (14)	0.12660 (17)	0.51524 (7)	0.0199 (2)
H17A	0.4187	0.1738	0.4714	0.024*
C18	0.64788 (14)	0.09259 (18)	0.50067 (8)	0.0245 (2)
H18A	0.6879	0.1175	0.4470	0.029*
C19	0.74952 (14)	0.02273 (19)	0.56382 (9)	0.0269 (3)
H19A	0.8587	−0.0014	0.5534	0.032*
C20	0.69096 (15)	−0.0119 (2)	0.64258 (9)	0.0269 (3)
H20A	0.7605	−0.0588	0.6863	0.032*
C21	0.53069 (14)	0.02215 (17)	0.65755 (7)	0.0216 (2)
H21A	0.4914	−0.0023	0.7114	0.026*
C22	−0.13252 (15)	−0.51842 (19)	0.62248 (8)	0.0253 (2)
H22A	−0.1096	−0.6038	0.5761	0.038*
H22B	−0.1525	−0.3903	0.6007	0.038*
H22C	−0.2273	−0.5636	0.6506	0.038*
C23	−0.23837 (15)	−0.72755 (19)	0.87505 (8)	0.0253 (3)
H23A	−0.2809	−0.8524	0.8589	0.038*
H23B	−0.3263	−0.6454	0.8915	0.038*
H23C	−0.1610	−0.7417	0.9223	0.038*
C24	0.47030 (15)	0.7900 (2)	0.91476 (8)	0.0273 (3)
H24A	0.4605	0.7778	0.9754	0.041*
H24B	0.4101	0.9013	0.8946	0.041*
H24C	0.5833	0.8050	0.9020	0.041*

	U11	U22	U33	U12	U13	U23
O1	0.0245 (4)	0.0245 (4)	0.0156 (4)	−0.0009 (3)	0.0033 (3)	−0.0029 (3)
O2	0.0243 (4)	0.0195 (4)	0.0182 (4)	0.0043 (3)	0.0001 (3)	−0.0029 (3)
O3	0.0264 (4)	0.0185 (4)	0.0230 (4)	−0.0020 (3)	0.0031 (3)	0.0031 (3)
N1	0.0191 (4)	0.0215 (5)	0.0156 (4)	0.0032 (4)	−0.0004 (3)	−0.0014 (4)
N2	0.0173 (4)	0.0184 (4)	0.0160 (4)	0.0033 (4)	0.0008 (3)	−0.0005 (4)
N3	0.0181 (4)	0.0199 (5)	0.0129 (4)	0.0010 (4)	0.0027 (3)	0.0003 (4)
C1	0.0141 (4)	0.0207 (5)	0.0152 (5)	0.0038 (4)	0.0025 (4)	0.0010 (4)
C2	0.0148 (4)	0.0196 (5)	0.0146 (5)	0.0047 (4)	0.0007 (4)	0.0011 (4)
C3	0.0161 (5)	0.0200 (5)	0.0159 (5)	0.0049 (4)	0.0000 (4)	0.0002 (4)
C4	0.0166 (5)	0.0188 (5)	0.0207 (5)	0.0030 (4)	−0.0007 (4)	0.0026 (4)
C5	0.0172 (5)	0.0239 (6)	0.0181 (5)	0.0037 (4)	0.0038 (4)	0.0038 (4)
C6	0.0193 (5)	0.0226 (5)	0.0142 (4)	0.0049 (4)	0.0022 (4)	0.0003 (4)
C7	0.0144 (5)	0.0197 (5)	0.0147 (4)	0.0040 (4)	0.0006 (4)	0.0006 (4)
C8	0.0156 (5)	0.0201 (5)	0.0143 (5)	0.0045 (4)	0.0012 (4)	−0.0001 (4)
C9	0.0174 (5)	0.0217 (6)	0.0152 (5)	0.0054 (4)	−0.0001 (4)	0.0002 (4)
C10	0.0191 (5)	0.0228 (6)	0.0171 (5)	0.0045 (4)	−0.0013 (4)	−0.0033 (4)
C11	0.0182 (5)	0.0198 (6)	0.0246 (5)	0.0045 (4)	−0.0028 (4)	−0.0030 (5)
C12	0.0210 (5)	0.0206 (6)	0.0246 (5)	0.0018 (4)	0.0006 (4)	0.0009 (4)
C13	0.0215 (5)	0.0196 (5)	0.0196 (5)	0.0022 (4)	0.0027 (4)	0.0020 (4)
C14	0.0166 (5)	0.0184 (5)	0.0156 (5)	0.0033 (4)	0.0003 (4)	0.0000 (4)
C15	0.0176 (5)	0.0215 (5)	0.0139 (4)	0.0018 (4)	0.0021 (4)	0.0020 (4)
C16	0.0174 (5)	0.0148 (5)	0.0182 (5)	−0.0001 (4)	0.0020 (4)	−0.0016 (4)
C17	0.0218 (5)	0.0170 (5)	0.0212 (5)	−0.0004 (4)	0.0037 (4)	−0.0002 (4)
C18	0.0253 (6)	0.0177 (5)	0.0313 (6)	−0.0036 (5)	0.0114 (5)	−0.0005 (5)
C19	0.0171 (5)	0.0208 (6)	0.0433 (7)	−0.0013 (4)	0.0058 (5)	−0.0043 (5)
C20	0.0216 (6)	0.0241 (6)	0.0346 (6)	0.0039 (5)	−0.0052 (5)	−0.0017 (5)
C21	0.0230 (5)	0.0211 (6)	0.0205 (5)	0.0031 (4)	−0.0004 (4)	−0.0011 (4)
C22	0.0304 (6)	0.0237 (6)	0.0214 (5)	−0.0029 (5)	−0.0042 (4)	−0.0009 (5)
C23	0.0236 (6)	0.0234 (6)	0.0290 (6)	−0.0007 (5)	0.0042 (5)	0.0065 (5)
C24	0.0243 (6)	0.0246 (6)	0.0327 (6)	−0.0004 (5)	−0.0018 (5)	−0.0076 (5)

O1—C1	1.2238 (14)	C11—C24	1.5027 (17)
O2—C3	1.3702 (14)	C12—C13	1.3538 (17)
O2—C22	1.4364 (14)	C12—H12A	0.9500
O3—C4	1.3634 (14)	C13—H13A	0.9500
O3—C23	1.4273 (15)	C15—C16	1.5162 (15)
N1—C9	1.3246 (16)	C15—H15A	0.9900
N1—C8	1.3772 (14)	C15—H15B	0.9900
N2—C13	1.3838 (15)	C16—C21	1.3932 (16)
N2—C14	1.3852 (16)	C16—C17	1.4001 (16)
N2—C9	1.4180 (14)	C17—C18	1.3905 (16)
N3—C14	1.3833 (14)	C17—H17A	0.9500
N3—C1	1.3983 (15)	C18—C19	1.384 (2)
N3—C15	1.4675 (14)	C18—H18A	0.9500
C1—C2	1.4888 (15)	C19—C20	1.3905 (19)
C2—C3	1.4093 (17)	C19—H19A	0.9500
C2—C7	1.4198 (15)	C20—C21	1.3920 (17)
C3—C4	1.4080 (15)	C20—H20A	0.9500
C4—C5	1.3956 (16)	C21—H21A	0.9500
C5—C6	1.3820 (18)	C22—H22A	0.9800
C5—H5A	0.9500	C22—H22B	0.9800
C6—C7	1.4015 (16)	C22—H22C	0.9800
C6—H6A	0.9500	C23—H23A	0.9800
C7—C8	1.4376 (16)	C23—H23B	0.9800
C8—C14	1.3735 (15)	C23—H23C	0.9800
C9—C10	1.4160 (17)	C24—H24A	0.9800
C10—C11	1.3689 (18)	C24—H24B	0.9800
C10—H10A	0.9500	C24—H24C	0.9800
C11—C12	1.4325 (16)
C3—O2—C22	114.36 (9)	N2—C13—H13A	120.2
C4—O3—C23	117.04 (10)	C8—C14—N3	124.06 (11)
C9—N1—C8	104.57 (9)	C8—C14—N2	106.58 (10)
C13—N2—C14	134.21 (10)	N3—C14—N2	129.36 (10)
C13—N2—C9	121.07 (10)	N3—C15—C16	113.18 (9)
C14—N2—C9	104.68 (9)	N3—C15—H15A	108.9
C14—N3—C1	120.01 (9)	C16—C15—H15A	108.9
C14—N3—C15	122.98 (10)	N3—C15—H15B	108.9
C1—N3—C15	116.91 (9)	C16—C15—H15B	108.9
O1—C1—N3	118.80 (10)	H15A—C15—H15B	107.8
O1—C1—C2	123.97 (11)	C21—C16—C17	118.79 (11)
N3—C1—C2	117.16 (9)	C21—C16—C15	122.45 (10)
C3—C2—C7	119.22 (10)	C17—C16—C15	118.75 (10)
C3—C2—C1	119.65 (10)	C18—C17—C16	120.31 (11)
C7—C2—C1	121.08 (10)	C18—C17—H17A	119.8
O2—C3—C4	118.08 (11)	C16—C17—H17A	119.8
O2—C3—C2	121.91 (10)	C19—C18—C17	120.50 (12)
C4—C3—C2	119.82 (10)	C19—C18—H18A	119.7
O3—C4—C5	125.26 (11)	C17—C18—H18A	119.7
O3—C4—C3	114.61 (10)	C18—C19—C20	119.63 (11)
C5—C4—C3	120.13 (11)	C18—C19—H19A	120.2
C6—C5—C4	120.28 (11)	C20—C19—H19A	120.2
C6—C5—H5A	119.9	C19—C20—C21	120.10 (12)
C4—C5—H5A	119.9	C19—C20—H20A	119.9
C5—C6—C7	120.85 (10)	C21—C20—H20A	119.9
C5—C6—H6A	119.6	C20—C21—C16	120.65 (11)
C7—C6—H6A	119.6	C20—C21—H21A	119.7
C6—C7—C2	119.51 (11)	C16—C21—H21A	119.7
C6—C7—C8	123.11 (10)	O2—C22—H22A	109.5
C2—C7—C8	117.35 (10)	O2—C22—H22B	109.5
C14—C8—N1	111.75 (10)	H22A—C22—H22B	109.5
C14—C8—C7	119.75 (10)	O2—C22—H22C	109.5
N1—C8—C7	128.45 (10)	H22A—C22—H22C	109.5
N1—C9—C10	129.72 (10)	H22B—C22—H22C	109.5
N1—C9—N2	112.40 (10)	O3—C23—H23A	109.5
C10—C9—N2	117.88 (10)	O3—C23—H23B	109.5
C11—C10—C9	121.21 (10)	H23A—C23—H23B	109.5
C11—C10—H10A	119.4	O3—C23—H23C	109.5
C9—C10—H10A	119.4	H23A—C23—H23C	109.5
C10—C11—C12	118.42 (11)	H23B—C23—H23C	109.5
C10—C11—C24	122.11 (11)	C11—C24—H24A	109.5
C12—C11—C24	119.46 (11)	C11—C24—H24B	109.5
C13—C12—C11	121.70 (12)	H24A—C24—H24B	109.5
C13—C12—H12A	119.2	C11—C24—H24C	109.5
C11—C12—H12A	119.2	H24A—C24—H24C	109.5
C12—C13—N2	119.60 (11)	H24B—C24—H24C	109.5
C12—C13—H13A	120.2

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···N1i	0.95	2.68	3.4126 (16)	134
C18—H18A···O1ii	0.95	2.36	3.1127 (16)	136
C19—H19A···O1iii	0.95	2.58	3.3840 (16)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯N1i	0.95	2.68	3.4126 (16)	134
C18—H18A⋯O1ii	0.95	2.36	3.1127 (16)	136
C19—H19A⋯O1iii	0.95	2.58	3.3840 (16)	142

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