1-(2-Azido­acet­yl)-3-methyl-2,6-diphenyl­piperidin-4-one

Yuvaraj, H.; Sundaramoorthy, S.; Velmurugan, D.; Kalkhambkar, R.G.

doi:10.1107/S1600536810039097

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2733

https://doi.org/10.1107/S1600536810039097

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1-(2-Azidoacetyl)-3-methyl-2,6-diphenylpiperidin-4-one

Haldorai Yuvaraj,^a ^* S. Sundaramoorthy,^b D. Velmurugan ^b and Rajesh G. Kalkhambkar ^c

^aSchool of Display and Chemical Engineering, Yeungnam University, Gyeongsan, Gyeongbuk 712-749, Republic of Korea, ^bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Chemistry, Karnatak University, Karnatak Science College, Dharwad 580 001, Karnataka, India
^*Correspondence e-mail: yuvraj_pd@yahoo.co.in

(Received 25 September 2010; accepted 30 September 2010; online 9 October 2010)

In the title compound, C₂₀H₂₀N₄O₂, the piperidine ring adopts a distorted boat conformation. The two phenyl rings form dihedral angles of 82.87 (1) and 84.40 (1)° with respect to the piperidine ring. The crystal packing is stabilized by intermolecular C—H⋯O and C—H⋯N interactions.

Related literature

For the biological activity of piperidines, see: Aridoss et al. (2008 , 2010 ). For ring conformational analysis, see: Cremer & Pople (1975 ); Nardelli (1983 ). For related structures, see: Jeyaraman et al. (1999 ); Keana & Cai (1990 ); Ponnuswamy et al. (2002 ).

Experimental

Crystal data

C₂₀H₂₀N₄O₂
M_r = 348.40
Monoclinic, P 2₁ /c
a = 11.0418 (3) Å
b = 15.7844 (5) Å
c = 10.5684 (3) Å
β = 108.458 (2)°
V = 1747.19 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 292 K
0.25 × 0.23 × 0.2 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.978, T_max = 0.983
16435 measured reflections
4286 independent reflections
3147 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.138
S = 1.05
4286 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1ⁱ	0.93	2.57	3.464 (2)	162
C5—H5⋯N2ⁱⁱ	0.98	2.52	3.353 (2)	142
C2—H2B⋯O2ⁱⁱ	0.97	2.56	3.4933 (19)	161
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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: https://doi.org/10.1107/S1600536810039097/bt5365sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039097/bt5365Isup2.hkl

checkCIF report

Comment top

2,6-Diarylpiperidin-4-ones normally adopt chair conformation with equatorial orientation of all the substituents. Nevertheless, introduction of some heteroconjugate groups such as –NO, –CHO, –COCH₃, –COC₆H₅, etc., at the heteroatom of 2,6-disubstitutedpiperidine ring system have reported to cause a major change in ring conformation, and orientation of the substituents (Jeyaraman et al., 1999; Ponnuswamy et al., 2002). To establish the conformational impact of azidoacetyl group at the nitrogen of 2,6-diphenyl -3-methylpiperidin-4-one, the current study has been undertaken.

The ORTEP plot of the title molecule is shown in Fig.1. The piperidine ring adopts a distorted boat conformation with the puckering parameters (Cremer & Pople, 1975) and asymmetry parameters (Nardelli, 1983) of q₂ = 0.699 (5) Å, q₃ = -0.043 (2) Å, φ₂ = 68.242 (8)° and Δ_s (C1 and C4) = 9.5 (2) Å. The sum of the bond angles around the atom N1[(355.42 (3)°] of the piperidine ring is in accordance with the sp² hybridization.

The crystal structure is stabilized by C—H···O and C—H···N intermolecular interactions which link the molecules into chains running along the c axis. Atoms C2 and C5 at (x, y, z) donate one proton to acceptor O2 and N2 at (-x + 1, -y, -z), forming a centrosymmetric dimers (Fig. 2) with R₂²(12) ring motifs.

Related literature top

For the biological activities, see: Aridoss et al. (2008, 2010). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983). For related structures, see: Jeyaraman et al. (1999); Keana & Cai (1990); Ponnuswamy et al. (2002).

Experimental top

1-(2-Azidoacetyl)-3-methyl-2,6-diphenylpiperidin-4-one was prepared from the reaction of 1-chloroacetyl-3-methyl-2,6-diphenylpiperidin -4-one with NaN₃ as per the reported procedure (Keana & Cai, 1990). The obtained crude mass was purified by column chromatography followed by recrystallization from ethanol giving colourless, diffraction quality crystals.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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. Perspective view of the molecule showing the thermal ellipsoids drawn at 30% probability level.
	Fig. 2. The crystal packing of the molecules viewed down a axis. For clarity, hydrogen atoms which are not involved in hydrogen bonding are omitted

1-(2-Azidoacetyl)-3-methyl-2,6-diphenylpiperidin-4-one top

Crystal data top

C₂₀H₂₀N₄O₂	F(000) = 736
M_r = 348.40	D_x = 1.324 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1520 reflections
a = 11.0418 (3) Å	θ = 1.9–28.5°
b = 15.7844 (5) Å	µ = 0.09 mm⁻¹
c = 10.5684 (3) Å	T = 292 K
β = 108.458 (2)°	Block, colourless
V = 1747.19 (9) Å³	0.25 × 0.23 × 0.2 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	4286 independent reflections
Radiation source: fine-focus sealed tube	3147 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and φ scans	θ_max = 28.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
T_min = 0.978, T_max = 0.983	k = −19→21
16435 measured reflections	l = −14→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0678P)² + 0.3241P] where P = (F_o² + 2F_c²)/3
4286 reflections	(Δ/σ)_max < 0.001
236 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₀H₂₀N₄O₂	V = 1747.19 (9) Å³
M_r = 348.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0418 (3) Å	µ = 0.09 mm⁻¹
b = 15.7844 (5) Å	T = 292 K
c = 10.5684 (3) Å	0.25 × 0.23 × 0.2 mm
β = 108.458 (2)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	4286 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3147 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.983	R_int = 0.026
16435 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.05	Δρ_max = 0.24 e Å⁻³
4286 reflections	Δρ_min = −0.18 e Å⁻³
236 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	0.59213 (13)	0.02968 (9)	0.33092 (13)	0.0366 (3)
H1	0.5050	0.0521	0.3073	0.044*
C2	0.57944 (14)	−0.06647 (9)	0.32572 (15)	0.0411 (3)
H2A	0.5489	−0.0853	0.3976	0.049*
H2B	0.5166	−0.0827	0.2421	0.049*
C3	0.70355 (14)	−0.10988 (9)	0.33785 (14)	0.0392 (3)
C4	0.80956 (13)	−0.05375 (9)	0.32448 (14)	0.0386 (3)
H4	0.8441	−0.0228	0.4087	0.046*
C5	0.75819 (13)	0.01278 (9)	0.21275 (13)	0.0360 (3)
H5	0.7324	−0.0182	0.1281	0.043*
C6	0.86401 (14)	0.07294 (9)	0.20829 (14)	0.0387 (3)
C7	0.92891 (16)	0.12263 (10)	0.31632 (17)	0.0498 (4)
H7	0.9025	0.1239	0.3916	0.060*
C8	1.03309 (18)	0.17048 (12)	0.3130 (2)	0.0638 (5)
H8	1.0764	0.2034	0.3863	0.077*
C9	1.07271 (18)	0.16958 (12)	0.2027 (2)	0.0661 (5)
H9	1.1430	0.2015	0.2012	0.079*
C10	1.00821 (19)	0.12146 (13)	0.0946 (2)	0.0670 (5)
H10	1.0341	0.1211	0.0190	0.080*
C11	0.90476 (17)	0.07345 (11)	0.09768 (17)	0.0536 (4)
H11	0.8617	0.0408	0.0238	0.064*
C12	0.91822 (16)	−0.10347 (11)	0.30249 (19)	0.0556 (4)
H12A	0.9447	−0.1471	0.3688	0.083*
H12B	0.9887	−0.0661	0.3093	0.083*
H12C	0.8903	−0.1287	0.2154	0.083*
C13	0.66501 (13)	0.06839 (9)	0.46567 (14)	0.0386 (3)
C14	0.70059 (15)	0.02104 (11)	0.58243 (15)	0.0489 (4)
H14	0.6877	−0.0373	0.5783	0.059*
C15	0.75481 (18)	0.05956 (14)	0.70438 (17)	0.0639 (5)
H15	0.7784	0.0269	0.7816	0.077*
C16	0.77431 (18)	0.14548 (15)	0.71305 (19)	0.0683 (6)
H16	0.8088	0.1713	0.7958	0.082*
C17	0.74226 (18)	0.19344 (12)	0.5977 (2)	0.0645 (5)
H17	0.7572	0.2515	0.6025	0.077*
C18	0.68785 (16)	0.15484 (10)	0.47485 (17)	0.0506 (4)
H18	0.6664	0.1874	0.3976	0.061*
C19	0.56623 (15)	0.09208 (9)	0.10767 (14)	0.0416 (3)
C20	0.43631 (16)	0.12667 (11)	0.10659 (16)	0.0531 (4)
H20A	0.3892	0.0822	0.1339	0.064*
H20B	0.4493	0.1726	0.1705	0.064*
N1	0.64214 (11)	0.05607 (7)	0.22287 (11)	0.0364 (3)
N2	0.36126 (14)	0.15755 (9)	−0.02523 (14)	0.0570 (4)
N3	0.38863 (12)	0.22845 (9)	−0.05698 (13)	0.0475 (3)
N4	0.39979 (17)	0.29178 (11)	−0.09966 (16)	0.0670 (4)
O1	0.71688 (12)	−0.18542 (7)	0.35828 (12)	0.0547 (3)
O2	0.59960 (12)	0.09701 (8)	0.00863 (11)	0.0566 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0380 (7)	0.0361 (7)	0.0357 (7)	0.0033 (5)	0.0116 (6)	0.0017 (6)
C2	0.0417 (7)	0.0383 (8)	0.0434 (8)	−0.0047 (6)	0.0138 (6)	−0.0010 (6)
C3	0.0512 (8)	0.0315 (7)	0.0369 (7)	0.0001 (6)	0.0168 (6)	0.0005 (6)
C4	0.0421 (7)	0.0328 (7)	0.0418 (8)	0.0028 (5)	0.0146 (6)	0.0015 (6)
C5	0.0416 (7)	0.0327 (7)	0.0337 (7)	−0.0015 (5)	0.0119 (6)	−0.0024 (5)
C6	0.0421 (7)	0.0339 (7)	0.0391 (7)	−0.0004 (5)	0.0114 (6)	0.0043 (6)
C7	0.0534 (9)	0.0450 (9)	0.0493 (9)	−0.0079 (7)	0.0137 (7)	−0.0027 (7)
C8	0.0559 (10)	0.0492 (10)	0.0768 (13)	−0.0137 (8)	0.0077 (9)	−0.0012 (9)
C9	0.0519 (10)	0.0532 (10)	0.0941 (15)	−0.0071 (8)	0.0244 (10)	0.0206 (10)
C10	0.0680 (12)	0.0710 (13)	0.0728 (13)	−0.0020 (10)	0.0375 (11)	0.0185 (10)
C11	0.0605 (10)	0.0582 (10)	0.0459 (9)	−0.0059 (8)	0.0222 (8)	0.0021 (7)
C12	0.0505 (9)	0.0487 (9)	0.0719 (11)	0.0104 (7)	0.0254 (9)	0.0090 (8)
C13	0.0379 (7)	0.0405 (8)	0.0376 (7)	0.0066 (5)	0.0124 (6)	−0.0014 (6)
C14	0.0516 (9)	0.0536 (10)	0.0410 (8)	0.0025 (7)	0.0139 (7)	0.0029 (7)
C15	0.0606 (11)	0.0864 (15)	0.0393 (9)	0.0048 (9)	0.0083 (8)	0.0006 (9)
C16	0.0568 (10)	0.0925 (16)	0.0474 (10)	0.0053 (10)	0.0049 (8)	−0.0255 (10)
C17	0.0606 (11)	0.0529 (10)	0.0714 (13)	0.0038 (8)	0.0087 (9)	−0.0231 (9)
C18	0.0559 (9)	0.0409 (8)	0.0501 (9)	0.0066 (7)	0.0099 (7)	−0.0051 (7)
C19	0.0483 (8)	0.0361 (7)	0.0344 (7)	−0.0034 (6)	0.0044 (6)	−0.0004 (6)
C20	0.0542 (9)	0.0537 (10)	0.0445 (9)	0.0093 (7)	0.0057 (7)	0.0037 (7)
N1	0.0403 (6)	0.0343 (6)	0.0330 (6)	0.0011 (5)	0.0093 (5)	0.0010 (5)
N2	0.0614 (8)	0.0418 (8)	0.0505 (8)	0.0023 (6)	−0.0070 (7)	0.0026 (6)
N3	0.0451 (7)	0.0496 (8)	0.0402 (7)	0.0029 (6)	0.0029 (6)	−0.0050 (6)
N4	0.0798 (11)	0.0576 (10)	0.0584 (10)	−0.0084 (8)	0.0145 (8)	0.0053 (8)
O1	0.0714 (8)	0.0328 (6)	0.0688 (8)	0.0034 (5)	0.0347 (6)	0.0067 (5)
O2	0.0614 (7)	0.0684 (8)	0.0369 (6)	0.0013 (6)	0.0112 (5)	0.0091 (5)

Geometric parameters (Å, º) top

C1—N1	1.4771 (17)	C10—H10	0.9300
C1—C2	1.5235 (19)	C11—H11	0.9300
C1—C13	1.5243 (19)	C12—H12A	0.9600
C1—H1	0.9800	C12—H12B	0.9600
C2—C3	1.501 (2)	C12—H12C	0.9600
C2—H2A	0.9700	C13—C18	1.386 (2)
C2—H2B	0.9700	C13—C14	1.389 (2)
C3—O1	1.2123 (16)	C14—C15	1.379 (2)
C3—C4	1.510 (2)	C14—H14	0.9300
C4—C12	1.512 (2)	C15—C16	1.372 (3)
C4—C5	1.5476 (19)	C15—H15	0.9300
C4—H4	0.9800	C16—C17	1.383 (3)
C5—N1	1.4856 (17)	C16—H16	0.9300
C5—C6	1.5179 (19)	C17—C18	1.387 (2)
C5—H5	0.9800	C17—H17	0.9300
C6—C11	1.379 (2)	C18—H18	0.9300
C6—C7	1.384 (2)	C19—O2	1.2172 (18)
C7—C8	1.386 (2)	C19—N1	1.3645 (18)
C7—H7	0.9300	C19—C20	1.532 (2)
C8—C9	1.369 (3)	C20—N2	1.461 (2)
C8—H8	0.9300	C20—H20A	0.9700
C9—C10	1.369 (3)	C20—H20B	0.9700
C9—H9	0.9300	N2—N3	1.233 (2)
C10—C11	1.380 (3)	N3—N4	1.119 (2)

N1—C1—C2	107.80 (11)	C10—C11—C6	121.20 (17)
N1—C1—C13	113.16 (11)	C10—C11—H11	119.4
C2—C1—C13	116.63 (12)	C6—C11—H11	119.4
N1—C1—H1	106.2	C4—C12—H12A	109.5
C2—C1—H1	106.2	C4—C12—H12B	109.5
C13—C1—H1	106.2	H12A—C12—H12B	109.5
C3—C2—C1	112.38 (12)	C4—C12—H12C	109.5
C3—C2—H2A	109.1	H12A—C12—H12C	109.5
C1—C2—H2A	109.1	H12B—C12—H12C	109.5
C3—C2—H2B	109.1	C18—C13—C14	118.28 (14)
C1—C2—H2B	109.1	C18—C13—C1	119.39 (13)
H2A—C2—H2B	107.9	C14—C13—C1	122.12 (13)
O1—C3—C2	121.36 (13)	C15—C14—C13	120.68 (17)
O1—C3—C4	122.66 (13)	C15—C14—H14	119.7
C2—C3—C4	115.97 (11)	C13—C14—H14	119.7
C3—C4—C12	112.72 (12)	C16—C15—C14	120.73 (18)
C3—C4—C5	111.22 (12)	C16—C15—H15	119.6
C12—C4—C5	110.61 (12)	C14—C15—H15	119.6
C3—C4—H4	107.3	C15—C16—C17	119.44 (17)
C12—C4—H4	107.3	C15—C16—H16	120.3
C5—C4—H4	107.3	C17—C16—H16	120.3
N1—C5—C6	113.86 (11)	C16—C17—C18	119.93 (18)
N1—C5—C4	111.92 (10)	C16—C17—H17	120.0
C6—C5—C4	110.39 (11)	C18—C17—H17	120.0
N1—C5—H5	106.7	C17—C18—C13	120.90 (17)
C6—C5—H5	106.7	C17—C18—H18	119.6
C4—C5—H5	106.7	C13—C18—H18	119.6
C11—C6—C7	118.25 (14)	O2—C19—N1	121.75 (14)
C11—C6—C5	119.41 (13)	O2—C19—C20	120.57 (13)
C7—C6—C5	122.12 (13)	N1—C19—C20	117.68 (13)
C6—C7—C8	120.36 (16)	N2—C20—C19	111.92 (14)
C6—C7—H7	119.8	N2—C20—H20A	109.2
C8—C7—H7	119.8	C19—C20—H20A	109.2
C9—C8—C7	120.50 (18)	N2—C20—H20B	109.2
C9—C8—H8	119.8	C19—C20—H20B	109.2
C7—C8—H8	119.8	H20A—C20—H20B	107.9
C8—C9—C10	119.64 (16)	C19—N1—C1	122.20 (12)
C8—C9—H9	120.2	C19—N1—C5	115.31 (11)
C10—C9—H9	120.2	C1—N1—C5	117.91 (10)
C9—C10—C11	120.04 (17)	N3—N2—C20	116.64 (14)
C9—C10—H10	120.0	N4—N3—N2	171.04 (17)
C11—C10—H10	120.0

N1—C1—C2—C3	57.25 (15)	N1—C1—C13—C14	−135.96 (14)
C13—C1—C2—C3	−71.29 (15)	C2—C1—C13—C14	−10.06 (19)
C1—C2—C3—O1	167.38 (13)	C18—C13—C14—C15	1.3 (2)
C1—C2—C3—C4	−12.02 (17)	C1—C13—C14—C15	−173.35 (14)
O1—C3—C4—C12	15.3 (2)	C13—C14—C15—C16	0.3 (3)
C2—C3—C4—C12	−165.33 (13)	C14—C15—C16—C17	−1.7 (3)
O1—C3—C4—C5	140.15 (14)	C15—C16—C17—C18	1.6 (3)
C2—C3—C4—C5	−40.45 (16)	C16—C17—C18—C13	−0.1 (3)
C3—C4—C5—N1	47.54 (15)	C14—C13—C18—C17	−1.4 (2)
C12—C4—C5—N1	173.60 (12)	C1—C13—C18—C17	173.41 (14)
C3—C4—C5—C6	175.48 (11)	O2—C19—C20—N2	4.4 (2)
C12—C4—C5—C6	−58.46 (16)	N1—C19—C20—N2	−175.73 (13)
N1—C5—C6—C11	−118.49 (15)	O2—C19—N1—C1	−163.94 (13)
C4—C5—C6—C11	114.64 (15)	C20—C19—N1—C1	16.16 (19)
N1—C5—C6—C7	67.05 (17)	O2—C19—N1—C5	−8.5 (2)
C4—C5—C6—C7	−59.82 (18)	C20—C19—N1—C5	171.63 (12)
C11—C6—C7—C8	−0.9 (2)	C2—C1—N1—C19	104.11 (14)
C5—C6—C7—C8	173.64 (15)	C13—C1—N1—C19	−125.40 (13)
C6—C7—C8—C9	0.4 (3)	C2—C1—N1—C5	−50.76 (15)
C7—C8—C9—C10	0.5 (3)	C13—C1—N1—C5	79.74 (14)
C8—C9—C10—C11	−0.7 (3)	C6—C5—N1—C19	76.01 (15)
C9—C10—C11—C6	0.2 (3)	C4—C5—N1—C19	−157.92 (12)
C7—C6—C11—C10	0.6 (2)	C6—C5—N1—C1	−127.41 (12)
C5—C6—C11—C10	−174.06 (16)	C4—C5—N1—C1	−1.34 (16)
N1—C1—C13—C18	49.44 (17)	C19—C20—N2—N3	−79.48 (19)
C2—C1—C13—C18	175.34 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	0.93	2.57	3.464 (2)	162
C5—H5···N2ⁱⁱ	0.98	2.52	3.353 (2)	142
C2—H2B···O2ⁱⁱ	0.97	2.56	3.4933 (19)	161

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀N₄O₂
M_r	348.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	292
a, b, c (Å)	11.0418 (3), 15.7844 (5), 10.5684 (3)
β (°)	108.458 (2)
V (Å³)	1747.19 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.23 × 0.2

Data collection
Diffractometer	Bruker SMART APEXII area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.978, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	16435, 4286, 3147
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.138, 1.05
No. of reflections	4286
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.18

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	0.93	2.57	3.464 (2)	162.2
C5—H5···N2ⁱⁱ	0.98	2.52	3.353 (2)	142.1
C2—H2B···O2ⁱⁱ	0.97	2.56	3.4933 (19)	161.0

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

Acknowledgements

HY acknowledges Yeungnam University for the opportunity to work as a Full-Time Foreign Instructor. SS and DV thank the TBI X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the University Grants Commission (UGC and SAP) for financial support.

References

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