3-Ethyl-5-(4-meth­oxy­phen­oxy)-2-(pyridin-4-yl)-3H-imidazo[4,5-b]pyridine

Ranjith, S.; SubbiahPandi, A.; Suresh, A.D.; Pitchumani, K.

doi:10.1107/S1600536811023543

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1764

doi:10.1107/S1600536811023543

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3-Ethyl-5-(4-methoxyphenoxy)-2-(pyridin-4-yl)-3H-imidazo[4,5-b]pyridine

S. Ranjith,^a A. SubbiahPandi,^a ^* A. D. Suresh ^b and K. Pitchumani ^b

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, India
^*Correspondence e-mail: a_sp59@yahoo.in

(Received 27 April 2011; accepted 16 June 2011; online 22 June 2011)

In the title compound, C₂₀H₁₈N₄O₂, the imidazopyridine fused ring system is almost perpendicular to the benzene ring [dihedral angle = 87.6 (5)°]. The pyridine ring makes a dihedral angle of 35.5 (5)° with the mean plane of the imidazopyridine fragment. The crystal structure is stabilized by an aromatic π–π stacking interaction between the phenyl rings of neighbouring molecules [centroid–centroid distance = 3.772 (2) Å, interplanar distance = 3.546 (2) Å and slippage = 1.286 (2) Å].

Related literature

For the biological activity of pyridine derivatives, see: Passannanti et al. (1998 ); Jiyeon et al. (2010 ); Abdel-Alim et al. (2005 ); Girgis et al. (2006 ); Slominska et al. (2008 ); Spanka et al. (2010 ). For a related structure, see: Ouzidan et al. (2010 ). For sp³ hybridization, see: Beddoes et al. (1986 ).

Experimental

Crystal data

C₂₀H₁₈N₄O₂
M_r = 346.38
Monoclinic, P 2₁ /c
a = 13.6591 (4) Å
b = 13.7104 (4) Å
c = 9.3177 (2) Å
β = 98.940 (1)°
V = 1723.74 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.981, T_max = 0.985
24827 measured reflections
5887 independent reflections
3938 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.140
S = 1.00
5887 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811023543/lx2189sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811023543/lx2189Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811023543/lx2189Isup3.cml

checkCIF report

Comment top

Pyridine derivatives has numerous applications in medicinal chemistry (Passannanti et al., 1998). Furthermore, the imidazo[4,5-b]pyridine moiety is also an important heterocyclic nucleus which has been used extensively in medicinal chemistry. In fact, the heterocycles derived from these intermediates have been tested for their potential as anti-neuroinflammatory (Jiyeon et al., 2010). Pyridine-3-carboxamides have gained attention because of their diverse pharmacological properties such as anti-inflammatory (Abdel-Alim et al., 2005), anticancer (Girgis et al., 2006), cytoprotective (Slominska et al., 2008), and anxiolytic (Spanka et al., 2010) activities. Against this background, and in order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound was carried out.

The bond lengths and angles in (Fig. 1) agree with those observed in other imidazopyridine derivatives (Ouzidan et al., 2010). The imidazopyridine ring system is essentially planar, with maximum deviation of 0.013 (1)° for atom C1. The sum of bond angles around N2[359.2 (9)°] of the imidazole ring is in accordance with sp³ hybridization (Beddoes et al., 1986). The imidazopyridine ring system makes dihedral angles of 35.5 (5) and 87.6 (5)°, respectively, with the pyridine and phenyl rings and also the dihedral angle between the pyridine and phenyl ring is 87.0 (6)°. It shows that the phenyl ring is perpendicular to both the imidazopyridine and pyridine rings. The atoms O1 and O2 are deviated by 0.039 (1) and - 0.021 (1)Å from the leastsquares plane of the phenyl ring.

The molecules lack hydrogen bonding functionality and pack in layers parallel to the (100) planes. The crystal structure is stabilized by an aromatic π–π stacking interaction between the phenyl rings of adjacent molecules, with a Cg···Cg distance of 3.772 (2) Å and an interplanar distance of 3.546 (3) Å resulting in a slippage of 1.286 (3) Å (Cg is the centroid of the C14–C19 phenyl ring).

Related literature top

For the biological activity of pyridine derivatives, see: Passannanti et al. (1998); Jiyeon et al. (2010); Abdel-Alim et al. (2005); Girgis et al. (2006); Slominska et al. (2008); Spanka et al. (2010). For a related structure, see: Ouzidan et al. (2010).

For sp³ hybridization, see: Beddoes et al. (1986).

Experimental top

N-ethyl-6-(4-methoxyphenoxy)pyridin-2-amine (0.23 g, 1 mmol) and amide (0.12 g, 1 mmol) successively added to Al³⁺–Y in xylene at 145°C. After stirring for 16 h, the mixture was diluted with dichloromethane. After removing the catalyst by filtration, followed by solvent evaporation, the resulting crude product was finally purified by column chromatography (silica gel). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in ethylacetate at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The structure of showing the atom-numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.

3-Ethyl-5-(4-methoxyphenoxy)-2-(pyridin-4-yl)-3H- imidazo[4,5-b]pyridine top

Crystal data top

C₂₀H₁₈N₄O₂	F(000) = 728
M_r = 346.38	D_x = 1.335 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5887 reflections
a = 13.6591 (4) Å	θ = 1.5–32.0°
b = 13.7104 (4) Å	µ = 0.09 mm⁻¹
c = 9.3177 (2) Å	T = 293 K
β = 98.940 (1)°	Block, white crystalline
V = 1723.74 (8) Å³	0.25 × 0.22 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	5887 independent reflections
Radiation source: fine-focus sealed tube	3938 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 10.0 pixels mm^-1	θ_max = 32.1°, θ_min = 1.5°
ω and ϕ scans	h = −20→20
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −20→20
T_min = 0.981, T_max = 0.985	l = −13→12
24827 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: difference Fourier map
wR(F²) = 0.140	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.068P)² + 0.2334P] where P = (F_o² + 2F_c²)/3
5887 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₀H₁₈N₄O₂	V = 1723.74 (8) Å³
M_r = 346.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.6591 (4) Å	µ = 0.09 mm⁻¹
b = 13.7104 (4) Å	T = 293 K
c = 9.3177 (2) Å	0.25 × 0.22 × 0.19 mm
β = 98.940 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5887 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3938 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.985	R_int = 0.027
24827 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.00	Δρ_max = 0.30 e Å⁻³
5887 reflections	Δρ_min = −0.20 e Å⁻³
237 parameters

Special details top

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
C1	0.34424 (9)	0.10472 (9)	0.42615 (13)	0.0383 (3)
C2	0.34457 (9)	0.18018 (9)	0.52777 (14)	0.0406 (3)
H2	0.3850	0.2344	0.5240	0.049*
C3	0.28465 (9)	0.17335 (9)	0.63296 (13)	0.0389 (3)
H3	0.2834	0.2222	0.7020	0.047*
C4	0.22585 (8)	0.09028 (8)	0.63192 (12)	0.0335 (2)
C5	0.23419 (8)	0.02078 (8)	0.52553 (12)	0.0330 (2)
C6	0.12671 (8)	−0.02604 (8)	0.66320 (12)	0.0332 (2)
C7	0.16889 (10)	−0.14643 (8)	0.46766 (13)	0.0403 (3)
H7A	0.1356	−0.1952	0.5182	0.048*
H7B	0.2363	−0.1683	0.4670	0.048*
C8	0.11655 (12)	−0.13785 (11)	0.31346 (15)	0.0547 (4)
H8A	0.0490	−0.1186	0.3137	0.082*
H8B	0.1181	−0.1997	0.2655	0.082*
H8C	0.1493	−0.0897	0.2629	0.082*
C9	0.05197 (8)	−0.08407 (8)	0.72257 (12)	0.0341 (2)
C10	0.05089 (10)	−0.08248 (9)	0.87147 (13)	0.0427 (3)
H10	0.0986	−0.0476	0.9329	0.051*
C11	−0.02193 (11)	−0.13343 (10)	0.92665 (15)	0.0500 (3)
H11	−0.0225	−0.1305	1.0262	0.060*
C12	−0.08936 (10)	−0.18810 (10)	0.70402 (15)	0.0459 (3)
H12	−0.1370	−0.2251	0.6457	0.055*
C13	−0.02073 (9)	−0.13820 (9)	0.63755 (13)	0.0386 (3)
H13	−0.0233	−0.1409	0.5373	0.046*
C14	0.40351 (9)	0.04175 (9)	0.22118 (14)	0.0425 (3)
C15	0.33767 (10)	0.04307 (10)	0.09494 (15)	0.0488 (3)
H15	0.2913	0.0930	0.0769	0.059*
C16	0.34062 (10)	−0.03057 (11)	−0.00606 (15)	0.0508 (3)
H16	0.2964	−0.0299	−0.0927	0.061*
C17	0.40900 (10)	−0.10480 (10)	0.02181 (15)	0.0479 (3)
C18	0.47462 (11)	−0.10467 (11)	0.14910 (16)	0.0546 (4)
H18	0.5211	−0.1544	0.1679	0.066*
C19	0.47204 (10)	−0.03162 (11)	0.24862 (16)	0.0512 (3)
H19	0.5167	−0.0318	0.3348	0.061*
C20	0.35584 (16)	−0.18189 (16)	−0.2055 (2)	0.0799 (5)
H20A	0.2878	−0.1767	−0.1920	0.120*
H20B	0.3653	−0.2416	−0.2555	0.120*
H20C	0.3727	−0.1276	−0.2621	0.120*
N1	0.29165 (7)	0.02406 (7)	0.42238 (11)	0.0374 (2)
N2	0.17080 (7)	−0.05379 (7)	0.54614 (10)	0.0340 (2)
N3	0.15774 (7)	0.05932 (7)	0.71772 (10)	0.0357 (2)
N4	−0.09155 (9)	−0.18655 (9)	0.84645 (13)	0.0512 (3)
O1	0.40353 (7)	0.11775 (7)	0.32231 (11)	0.0511 (2)
O2	0.41700 (9)	−0.18162 (9)	−0.06945 (12)	0.0716 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0354 (6)	0.0366 (6)	0.0433 (6)	−0.0005 (4)	0.0079 (5)	0.0034 (5)
C2	0.0382 (6)	0.0315 (6)	0.0517 (7)	−0.0044 (5)	0.0052 (5)	−0.0009 (5)
C3	0.0407 (6)	0.0313 (5)	0.0433 (6)	−0.0008 (5)	0.0022 (5)	−0.0056 (5)
C4	0.0353 (5)	0.0304 (5)	0.0338 (5)	0.0009 (4)	0.0027 (4)	−0.0008 (4)
C5	0.0350 (5)	0.0299 (5)	0.0338 (5)	0.0000 (4)	0.0042 (4)	0.0004 (4)
C6	0.0364 (5)	0.0316 (5)	0.0318 (5)	0.0020 (4)	0.0057 (4)	0.0008 (4)
C7	0.0471 (7)	0.0287 (5)	0.0468 (7)	−0.0017 (5)	0.0128 (5)	−0.0070 (5)
C8	0.0681 (9)	0.0502 (8)	0.0454 (7)	−0.0077 (7)	0.0075 (7)	−0.0135 (6)
C9	0.0375 (6)	0.0297 (5)	0.0360 (5)	0.0038 (4)	0.0084 (4)	0.0031 (4)
C10	0.0508 (7)	0.0416 (6)	0.0365 (6)	−0.0059 (5)	0.0091 (5)	−0.0021 (5)
C11	0.0647 (9)	0.0483 (7)	0.0403 (7)	−0.0071 (6)	0.0187 (6)	0.0014 (6)
C12	0.0408 (7)	0.0469 (7)	0.0496 (7)	−0.0049 (5)	0.0064 (5)	0.0004 (6)
C13	0.0394 (6)	0.0402 (6)	0.0357 (6)	0.0012 (5)	0.0044 (5)	0.0025 (5)
C14	0.0419 (6)	0.0421 (6)	0.0470 (7)	−0.0027 (5)	0.0181 (5)	0.0038 (5)
C15	0.0454 (7)	0.0443 (7)	0.0571 (8)	0.0077 (6)	0.0097 (6)	0.0095 (6)
C16	0.0489 (7)	0.0559 (8)	0.0462 (7)	0.0039 (6)	0.0025 (6)	0.0070 (6)
C17	0.0490 (7)	0.0491 (7)	0.0473 (7)	0.0052 (6)	0.0129 (6)	0.0019 (6)
C18	0.0499 (8)	0.0579 (9)	0.0554 (8)	0.0177 (7)	0.0060 (6)	0.0030 (7)
C19	0.0466 (7)	0.0594 (9)	0.0468 (7)	0.0080 (6)	0.0045 (6)	0.0042 (6)
C20	0.0881 (13)	0.0854 (13)	0.0627 (11)	0.0002 (11)	0.0005 (9)	−0.0198 (10)
N1	0.0399 (5)	0.0342 (5)	0.0396 (5)	−0.0011 (4)	0.0109 (4)	−0.0010 (4)
N2	0.0402 (5)	0.0285 (4)	0.0342 (5)	−0.0025 (4)	0.0085 (4)	−0.0030 (4)
N3	0.0396 (5)	0.0329 (5)	0.0346 (5)	0.0001 (4)	0.0060 (4)	−0.0017 (4)
N4	0.0538 (7)	0.0511 (7)	0.0517 (7)	−0.0089 (5)	0.0174 (5)	0.0016 (5)
O1	0.0557 (6)	0.0447 (5)	0.0585 (6)	−0.0112 (4)	0.0262 (5)	−0.0036 (4)
O2	0.0796 (8)	0.0689 (7)	0.0634 (7)	0.0212 (6)	0.0021 (6)	−0.0142 (6)

Geometric parameters (Å, º) top

C1—N1	1.3161 (15)	C10—H10	0.9300
C1—O1	1.3667 (14)	C11—N4	1.3312 (18)
C1—C2	1.4020 (17)	C11—H11	0.9300
C2—C3	1.3744 (17)	C12—N4	1.3322 (17)
C2—H2	0.9300	C12—C13	1.3823 (17)
C3—C4	1.3928 (16)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C4—N3	1.3842 (14)	C14—C15	1.365 (2)
C4—C5	1.3924 (15)	C14—C19	1.3708 (19)
C5—N1	1.3328 (14)	C14—O1	1.4048 (16)
C5—N2	1.3724 (14)	C15—C16	1.385 (2)
C6—N3	1.3192 (14)	C15—H15	0.9300
C6—N2	1.3788 (13)	C16—C17	1.3784 (19)
C6—C9	1.4686 (15)	C16—H16	0.9300
C7—N2	1.4638 (14)	C17—O2	1.3687 (17)
C7—C8	1.5066 (19)	C17—C18	1.371 (2)
C7—H7A	0.9700	C18—C19	1.369 (2)
C7—H7B	0.9700	C18—H18	0.9300
C8—H8A	0.9600	C19—H19	0.9300
C8—H8B	0.9600	C20—O2	1.406 (2)
C8—H8C	0.9600	C20—H20A	0.9600
C9—C13	1.3857 (17)	C20—H20B	0.9600
C9—C10	1.3899 (16)	C20—H20C	0.9600
C10—C11	1.3786 (18)

N1—C1—O1	118.16 (10)	N4—C12—C13	124.07 (13)
N1—C1—C2	125.63 (11)	N4—C12—H12	118.0
O1—C1—C2	116.21 (10)	C13—C12—H12	118.0
C3—C2—C1	119.44 (11)	C12—C13—C9	118.98 (11)
C3—C2—H2	120.3	C12—C13—H13	120.5
C1—C2—H2	120.3	C9—C13—H13	120.5
C2—C3—C4	117.22 (11)	C15—C14—C19	120.64 (13)
C2—C3—H3	121.4	C15—C14—O1	119.97 (12)
C4—C3—H3	121.4	C19—C14—O1	119.35 (13)
N3—C4—C5	109.76 (10)	C14—C15—C16	119.40 (13)
N3—C4—C3	133.26 (10)	C14—C15—H15	120.3
C5—C4—C3	116.98 (10)	C16—C15—H15	120.3
N1—C5—N2	125.53 (10)	C17—C16—C15	120.04 (13)
N1—C5—C4	127.79 (10)	C17—C16—H16	120.0
N2—C5—C4	106.68 (9)	C15—C16—H16	120.0
N3—C6—N2	113.32 (9)	O2—C17—C18	115.72 (12)
N3—C6—C9	122.41 (10)	O2—C17—C16	124.63 (13)
N2—C6—C9	124.27 (10)	C18—C17—C16	119.66 (13)
N2—C7—C8	112.19 (10)	C19—C18—C17	120.31 (13)
N2—C7—H7A	109.2	C19—C18—H18	119.8
C8—C7—H7A	109.2	C17—C18—H18	119.8
N2—C7—H7B	109.2	C18—C19—C14	119.94 (13)
C8—C7—H7B	109.2	C18—C19—H19	120.0
H7A—C7—H7B	107.9	C14—C19—H19	120.0
C7—C8—H8A	109.5	O2—C20—H20A	109.5
C7—C8—H8B	109.5	O2—C20—H20B	109.5
H8A—C8—H8B	109.5	H20A—C20—H20B	109.5
C7—C8—H8C	109.5	O2—C20—H20C	109.5
H8A—C8—H8C	109.5	H20A—C20—H20C	109.5
H8B—C8—H8C	109.5	H20B—C20—H20C	109.5
C13—C9—C10	117.46 (11)	C1—N1—C5	112.91 (10)
C13—C9—C6	123.59 (10)	C5—N2—C6	105.53 (9)
C10—C9—C6	118.91 (11)	C5—N2—C7	122.62 (9)
C11—C10—C9	118.99 (12)	C6—N2—C7	131.19 (9)
C11—C10—H10	120.5	C6—N3—C4	104.72 (9)
C9—C10—H10	120.5	C11—N4—C12	116.31 (11)
N4—C11—C10	124.17 (12)	C1—O1—C14	116.08 (9)
N4—C11—H11	117.9	C17—O2—C20	117.96 (13)
C10—C11—H11	117.9

N1—C1—C2—C3	−1.3 (2)	O1—C14—C19—C18	−178.17 (12)
O1—C1—C2—C3	178.21 (11)	O1—C1—N1—C5	−177.83 (11)
C1—C2—C3—C4	−0.17 (18)	C2—C1—N1—C5	1.63 (18)
C2—C3—C4—N3	−179.45 (12)	N2—C5—N1—C1	179.15 (11)
C2—C3—C4—C5	0.96 (16)	C4—C5—N1—C1	−0.73 (17)
N3—C4—C5—N1	179.77 (11)	N1—C5—N2—C6	−179.62 (11)
C3—C4—C5—N1	−0.54 (18)	C4—C5—N2—C6	0.28 (12)
N3—C4—C5—N2	−0.12 (13)	N1—C5—N2—C7	8.72 (18)
C3—C4—C5—N2	179.56 (10)	C4—C5—N2—C7	−171.38 (10)
N3—C6—C9—C13	142.45 (12)	N3—C6—N2—C5	−0.36 (13)
N2—C6—C9—C13	−37.09 (17)	C9—C6—N2—C5	179.21 (10)
N3—C6—C9—C10	−35.08 (17)	N3—C6—N2—C7	170.30 (11)
N2—C6—C9—C10	145.39 (12)	C9—C6—N2—C7	−10.13 (19)
C13—C9—C10—C11	−0.54 (19)	C8—C7—N2—C5	−76.72 (15)
C6—C9—C10—C11	177.14 (12)	C8—C7—N2—C6	113.98 (14)
C9—C10—C11—N4	1.3 (2)	N2—C6—N3—C4	0.28 (13)
N4—C12—C13—C9	1.1 (2)	C9—C6—N3—C4	−179.30 (10)
C10—C9—C13—C12	−0.60 (17)	C5—C4—N3—C6	−0.09 (13)
C6—C9—C13—C12	−178.16 (11)	C3—C4—N3—C6	−179.70 (13)
C19—C14—C15—C16	−0.1 (2)	C10—C11—N4—C12	−0.8 (2)
O1—C14—C15—C16	177.83 (11)	C13—C12—N4—C11	−0.4 (2)
C14—C15—C16—C17	0.6 (2)	N1—C1—O1—C14	−0.86 (17)
C15—C16—C17—O2	178.89 (13)	C2—C1—O1—C14	179.63 (11)
C15—C16—C17—C18	−0.7 (2)	C15—C14—O1—C1	90.64 (14)
O2—C17—C18—C19	−179.25 (14)	C19—C14—O1—C1	−91.40 (14)
C16—C17—C18—C19	0.4 (2)	C18—C17—O2—C20	−175.90 (15)
C17—C18—C19—C14	0.1 (2)	C16—C17—O2—C20	4.5 (2)
C15—C14—C19—C18	−0.2 (2)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₄O₂
M_r	346.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.6591 (4), 13.7104 (4), 9.3177 (2)
β (°)	98.940 (1)
V (Å³)	1723.74 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.22 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	24827, 5887, 3938
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.747

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.140, 1.00
No. of reflections	5887
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.20

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

SR and ASP thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

Abdel-Alim, A. M., El-Shorbagi, A. A., Abdel-Mothy, S. G. & Abdel-Allah, H. H. M. (2005). Arch. Pharm. Res. 28, 637–647. Web of Science PubMed CAS Google Scholar
Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787–797. CSD CrossRef Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Girgis, A. S., Hosni, H. M. & Barsoum, F. F. (2006). Bioorg. Med. Chem. 14, 4466-4476. Web of Science CrossRef PubMed CAS Google Scholar
Jiyeon, O., Sangseop, K., Kyu-Yang, Y., Nak-Jung, K., Hyung, S. H., Je-Yoel, C. & Kyoungho, S. (2010). Biochem. Pharmacol. 79, 596–609. Web of Science PubMed Google Scholar
Ouzidan, Y., Obbade, S., Capet, F., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o946. Web of Science CrossRef IUCr Journals Google Scholar
Passannanti, A., Diana, P., Barraja, P., Mingoia, F., Lauria, A. & Cirrincione, G. (1998). Heterocycles, 48, 1229–1235. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Slominska, E. M., Yuen, A., Osman, L., Gebicki, J., Yacoub, M. H. & Smolenski, R. T. (2008). Nucleoside Nucleotides Nucleic Acids, 27, 863–866. CrossRef CAS Google Scholar
Spanka, C., Glatthar, R., Desrayaud, S., Fendt, M., Orain, D., Troxler, T. & Vranesic, I. (2010). Bioorg. Med. Chem. Lett. 20, 184–188. Web of Science CrossRef PubMed CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar