6-Benzyl-3,4-dimeth­oxy-10-methyl­pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one

Meindl, K.; Stern, D.; Mert-Balci, F.; Beifuss, U.

doi:10.1107/S1600536809035806

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages o2464-o2465

doi:10.1107/S1600536809035806

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6-Benzyl-3,4-dimethoxy-10-methylpyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one

Kathrin Meindl,^a ^* Daniel Stern,^a Fadime Mert-Balci ^b and Uwe Beifuss ^b

^aInstitut für Anorganische Chemie, Universität Göttingen, Tammannstrasse 4, 37077 Göttingen, Germany, and ^bBioorganische Chemie, Institut für Chemie, Universität Hohenheim, Garbenstrasse 30, 70599 Stuttgart, Germany
^*Correspondence e-mail: meindl@shelx.uni-ac.gwdg.de

(Received 13 May 2009; accepted 4 September 2009; online 12 September 2009)

Pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-ones such as the title compound, C₂₄H₂₁N₃O₃, can be obtained in a few minutes in a microwave-assisted three-component reaction from 2-aminopyridines, isocyanides and 2-carboxybenzaldehydes. 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 intermolecular 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_r = 399.44
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.080
S = 1.06
4479 reflections
274 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 1895 Friedel pairs
Flack parameter: 0.2 (6)

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) $[-x, y-{\script{1\over 2}}, -z+2]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iii) x+1, y, z.

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.

Supporting information

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

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

checkCIF report

Comment top

The fused imidazo[1,2-a]heterocycles have proven to be successful in the field of medicinal chemistry. They show important biological activities like antibacterial, antiviral, antifungal and anti-inflammatory properties (Gueiffier et al., 1998, Almirante et al., 1965, Varma & Kumar, 1999, Sanfilippo et al., 1988). This heterocyclic structure element is present in drugs like alpidem (anxiolytic), zolpidem (hypnotic) and zolimidine (antiulcer) (Meng et al., 2007). Recently, pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-ones, incorporating an imidazopyridine backbone, have been reported to exhibit potent antitumor activity in vitro (Meng et al., 2007).

Pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-ones can be readily synthesized by the three-component reaction between 2-aminopyridines, isocyanides and 2-carboxybenzaldehydes under acidic conditions with the use of microwaves within a few minutes (Mert-Balci et al., 2008). The title compound (Fig. 1) was obtained from the corresponding compounds under similar conditions (Fig. 3). The pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-one ring system is almost planar with a mean deviation from the plane of 0.0681 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 molecules are hydrogen-bonded through hydrogen atoms at the benzyl carbon atoms C18 and C19, respectively, acting as donors towards the carbonyl oxygen atom O1 in different symmetry equivalent molecules, and by the hydrogen atom at C5 donating towards the imidazole nitrogen atom N1 (Fig. 2), thus forming a 3-dimensional network.

Related literature top

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 top

1 (1 mmol), 2 (1.09 mmol) and 3 (2.25 mmol) were suspended in toluene (2 ml) and placed in a 10 ml reaction vial that had been heated and cooled under argon. After the addition of MsOH (0.2 mmol), the vial was sealed with a septum and irradiated with microwaves (Discover by CEM; 2450 MHz; 300 W) at 160 °C for 7 min. The reaction mixture was allowed to cool to room temperature, diluted with CH₂Cl₂ (100 ml), and then washed with NaHCO₃ solution (2 × 100 ml). The residue obtained after drying the organic phase over MgSO₄ and concentration in vacuo was purified by column chromatography on silica gel (EtOAc) to yield the title compound 4 (yield 23%, m.p. 245–247°C). Crystallization from ethyl acetate provided suitable crystals of 4 for X-ray crystal structure analysis.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and 50% probability displacement ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. Hydrogen network in the crystal packing of the title compound. For clarity only H atoms involved in hydrogen bonds are shown. [Symmetry codes: (i) - x, y - 1/2, - z + 2; (ii) -x + 1, y + 1/2, - z + 1; (iii) x + 1, y, z; (iv) x - 1, y, z; (v) -x, y + 1/2, - z + 2; (vi) - x + 1, y - 1/2, - z + 1.]
	Fig. 3. Microwave-assisted synthesis of the title compound.

6-Benzyl-3,4-dimethoxy-9-methylpyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-one top

Crystal data top

C₂₄H₂₁N₃O₃	F(000) = 420
M_r = 399.44	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0521P)² + 0.1311P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
4479 reflections	Δρ_max = 0.23 e Å⁻³
274 parameters	Δρ_min = −0.20 e Å⁻³
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.2 (6)

Crystal data top

C₂₄H₂₁N₃O₃	V = 941.8 (3) Å³
M_r = 399.44	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.3650 (17) Å	µ = 0.10 mm⁻¹
b = 7.0500 (14) Å	T = 100 K
c = 15.983 (3) Å	0.35 × 0.20 × 0.20 mm
β = 92.27 (3)°

Data collection top

Bruker APEXII diffractometer	4479 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	4383 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.981	R_int = 0.021
16260 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.080	Δρ_max = 0.23 e Å⁻³
S = 1.06	Δρ_min = −0.20 e Å⁻³
4479 reflections	Absolute structure: Flack (1983)
274 parameters	Absolute structure parameter: 0.2 (6)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+2; (ii) −x+1, y+1/2, −z+1; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₁N₃O₃
M_r	399.44
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	8.3650 (17), 7.0500 (14), 15.983 (3)
β (°)	92.27 (3)
V (Å³)	941.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.965, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	16260, 4479, 4383
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.080, 1.06
No. of reflections	4479
No. of parameters	274
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.20
Absolute structure	Flack (1983)
Absolute structure parameter	0.2 (6)

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···N1ⁱ	0.95	2.68	3.4126 (16)	133.9
C18—H18A···O1ⁱⁱ	0.95	2.36	3.1127 (16)	135.8
C19—H19A···O1ⁱⁱⁱ	0.95	2.58	3.3840 (16)	142.3

Symmetry codes: (i) −x, y−1/2, −z+2; (ii) −x+1, y+1/2, −z+1; (iii) x+1, y, z.

Acknowledgements

Financial support by the BMBF (01RI05181) is greatly acknowledged.

References

Almirante, L., Polo, L., Mugnaini, A., Provinciali, E., Rugarli, P., Biancotti, A., Gamba, A. & Murmann, W. (1965). J. Med. Chem. 8, 305–312. CrossRef PubMed CAS Web of Science Google Scholar
Bruker (2006). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gueiffier, A., Mavel, S., Lhassani, M., Elhakmaoui, A., Snoeck, R., Andrei, G., Chavignon, O., Teulade, J.-C., Witvrouw, M., Balzarini, J., De Clercq, E. & Chapat, J.-P. (1998). J. Med. Chem. 41, 5108–5112. Web of Science CrossRef CAS PubMed Google Scholar
Meng, T., Zhang, Z., Hu, D., Lin, L., Ding, J., Wang, X. & Shen, J. (2007). J. Comb. Chem. 9, 739–741. Web of Science CrossRef PubMed CAS Google Scholar
Mert-Balci, F., Conrad, J., Meindl, K., Schulz, T., Stalke, D. & Beifuss, U. (2008). Synthesis, pp. 3649–3656. Google Scholar
Sanfilippo, P. J., Urbanski, M., Press, J. B., Dubinsky, B. & Moore, J. B. Jr (1988). J. Med. Chem. 31, 2221–2227. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Varma, R. S. & Kumar, D. (1999). Tetrahedron Lett. 40, 7665–7669. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 10| October 2009| Pages o2464-o2465

doi:10.1107/S1600536809035806

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

6-Benzyl-3,4-dimeth­­oxy-10-methyl­pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6-Benzyl-3,4-dimethoxy-10-methylpyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one