6-(4-Amino­phen­yl)-4-(4-eth­oxy­phen­yl)-2-meth­oxy­nicotinonitrile

Suwunwong, T.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536812036276

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Pages o2812-o2813

doi:10.1107/S1600536812036276

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6-(4-Aminophenyl)-4-(4-ethoxyphenyl)-2-methoxynicotinonitrile

Thitipone Suwunwong,^a Suchada Chantrapromma ^b ^*‡ and Hoong-Kun Fun ^c §

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 6 August 2012; accepted 20 August 2012; online 31 August 2012)

In the title molecule, C₂₁H₁₉N₃O₂, the central pyridine ring makes dihedral angles of 14.46 (9) and 34.67 (8)° with the 4-amino- and 4-ethoxy-substituted benzene rings, respectively. The ethoxy group is essentially coplanar with the attached benzene ring [C—O—C—C torsion angle = 178.70 (16)°] as is the methoxy group with the pyridine ring [C—O—C—N torsion angle = −3.0 (3)°]. In the crystal, molecules are linked by N—H⋯N hydrogen bonds into chains along [201]. Weak C—H⋯O hydrogen bonds and C—H⋯π interactions are also present.

Related literature

The title nicotinonitrile derivative is a cyclized product of a chalcone and a malononitrile in the present of sodium methoxide. For the synthesis and applications of substituted pyridines and nicotinonitrile derivatives, see: Al-Jaber et al. (2012 ); Brandt et al. (2010 ); El-Sayed et al. (2011 ); Goda et al. (2004 ); Ji et al. (2007 ); Kamal et al. (2007 ); Kim et al. (2005 ); Kolev et al. (2005 ); Koner et al. (2012 ); Zhou et al. (2006 ). For a related structure, see: Chantrapromma et al. (2010 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₁₉N₃O₂
M_r = 345.39
Monoclinic, P 2₁ /c
a = 5.3924 (2) Å
b = 16.5111 (5) Å
c = 20.1415 (6) Å
β = 91.315 (2)°
V = 1792.82 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.54 × 0.25 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.956, T_max = 0.982
17814 measured reflections
5216 independent reflections
3013 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.159
S = 1.04
5216 reflections
245 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H2N3⋯N2ⁱ	0.88 (3)	2.20 (3)	3.084 (3)	177 (2)
C21—H21A⋯O1ⁱⁱ	0.96	2.52	3.439 (2)	160
C18—H18A⋯Cgⁱⁱⁱ	0.96	2.84	3.7135 (18)	151
Symmetry codes: (i) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812036276/lh5514sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812036276/lh5514Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812036276/lh5514Isup3.cml

checkCIF report

Comment top

Pyridines have been reported for their applications in a number of areas (Goda et al., 2004; Kamal et al., 2007; Kolev et al., 2005). There are several methods reported for the synthesis of substituted pyridine derivatives including nicotinonitrile derivatives (Al-Jaber et al., 2012; Zhou et al., 2006). Nicotinonitrile derivatives have a wide range of applications such as antitumor, antimicrobial, analgesic, anti-hyperglycemic and antiproliferative activities (Brandt et al., 2010; El-Sayed et al., 2011; Ji et al., 2007; Kim et al., 2005) and fluorescent materials (Koner et al., 2012). Our research is aimed at the synthesis and preliminary fluorescent and antibacterial screening of nicotinonitrile derivatives. The title compound (I) was synthesized by the cyclization of a chalcone derivative with malononitrile to investigate its fluorescent properties. It was found that (I) exhibits fluorescence with the maximum emission at 498 nm when was excited at 370 nm in DMSO.

The molecular structure of the title compound is shown in Fig. 1. The central pyridine ring is inclined to the 4-aminophenyl and 4-ethoxyphenyl rings with the dihedral angles of 14.46 (9) and 34.67 (8)°, respectively. The dihedral angle between these two substituted benzene rings is 44.84 (9)°. The ethoxy substituent of the 4-ethoxyphenyl group is essentially co-planar with the attached benzene ring with the torsion angle C15–O1–C18–C19 = 178.70 (16)° and C18–O1–C15–C16 = 1.8 (3)°. The methoxy group is also approximately co-planar to the pyridine ring as indictated by the torsion angle C21–O2–C11–N1 = -3.0 (3)°. The bond distances agree with the literature values (Allen et al., 1987) and are comparable with those for a related structure (Chantrapromma et al., 2010).

In the crystal (Fig. 2), molecules are linked by N—H···N hydrogen bonds into chains along [201]. Weak C—H···O hydrogen bonds and C—H···π interactions are also present (Table 1).

Related literature top

The title nicotinonitrile derivative is a cyclized product of a chalcone and a malononitrile in the present of sodium methoxide. For the synthesis and applications of substituted pyridines and nicotinonitrile derivatives, see: Al-Jaber et al. (2012); Brandt et al. (2010); El-Sayed et al. (2011); Goda et al. (2004); Ji et al. (2007); Kamal et al. (2007); Kim et al. (2005); Kolev et al. (2005); Koner et al. (2012); Zhou et al. (2006). For a related structure, see: Chantrapromma et al. (2010). For standard bond-length data, see: Allen et al. (1987).

Experimental top

The title compound (I) was synthesized by stirring the solution of (E)-1-(4-aminophenyl)-3-(4-ethoxyphenyl)prop-2-en-1-one (0.27 g, 1 mmol) in methanol (10 ml) with a freshly prepared sodium methoxide (1.0 mmol of sodium in 20 ml of methanol). Excess malononitrile (0.13 g, 2.0 mmol) was then added with continuous stirring at room temperature until the precipitate was separated out. The resulting solid was filtered. Pale brown block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from methanol/ethanol (1:1 v/v) by the slow evaporation of the solvent at room temperature over several days, Mp. 477–478 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.

Fig. 2. The crystal packing of the title compound viewed along the a axis. Hydrogen bonds are shown as dashed lines.

6-(4-Aminophenyl)-4-(4-ethoxyphenyl)-2-methoxynicotinonitrile top

Crystal data top

C₂₁H₁₉N₃O₂	F(000) = 728
M_r = 345.39	D_x = 1.280 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 477–478 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.3924 (2) Å	Cell parameters from 5216 reflections
b = 16.5111 (5) Å	θ = 2.0–30.0°
c = 20.1415 (6) Å	µ = 0.08 mm⁻¹
β = 91.315 (2)°	T = 298 K
V = 1792.82 (10) Å³	Block, pale-brown
Z = 4	0.54 × 0.25 × 0.22 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	5216 independent reflections
Radiation source: sealed tube	3013 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
T_min = 0.956, T_max = 0.982	k = −23→23
17814 measured reflections	l = −28→28

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0647P)² + 0.3033P] where P = (F_o² + 2F_c²)/3
5216 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₁H₁₉N₃O₂	V = 1792.82 (10) Å³
M_r = 345.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.3924 (2) Å	µ = 0.08 mm⁻¹
b = 16.5111 (5) Å	T = 298 K
c = 20.1415 (6) Å	0.54 × 0.25 × 0.22 mm
β = 91.315 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5216 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3013 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.982	R_int = 0.028
17814 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.19 e Å⁻³
5216 reflections	Δρ_min = −0.16 e Å⁻³
245 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
O1	0.3134 (2)	0.38320 (7)	0.14470 (6)	0.0637 (3)
O2	1.3927 (3)	0.09389 (7)	0.37553 (7)	0.0737 (4)
N1	1.3663 (3)	0.21531 (8)	0.43089 (6)	0.0543 (3)
N2	1.0455 (4)	0.08668 (10)	0.23879 (9)	0.0858 (6)
N3	1.6313 (5)	0.48378 (15)	0.64781 (10)	0.0987 (7)
C1	1.5687 (4)	0.32043 (10)	0.52550 (9)	0.0654 (5)
H1A	1.6556	0.2743	0.5133	0.078*
C2	1.6575 (4)	0.36652 (11)	0.57804 (9)	0.0675 (5)
H2A	1.8018	0.3506	0.6006	0.081*
C3	1.5363 (4)	0.43554 (12)	0.59760 (9)	0.0663 (5)
C4	1.3212 (5)	0.45547 (16)	0.56331 (12)	0.1042 (9)
H4A	1.2332	0.5012	0.5759	0.125*
C5	1.2329 (4)	0.40959 (14)	0.51089 (11)	0.0874 (7)
H5A	1.0877	0.4254	0.4887	0.105*
C6	1.3538 (3)	0.34094 (10)	0.49045 (8)	0.0514 (4)
C7	1.2622 (3)	0.28980 (9)	0.43520 (8)	0.0501 (4)
C8	1.0805 (3)	0.31513 (10)	0.38963 (8)	0.0540 (4)
H8A	1.0110	0.3663	0.3941	0.065*
C9	1.0004 (3)	0.26572 (9)	0.33750 (7)	0.0485 (4)
C10	1.1104 (3)	0.18863 (9)	0.33383 (8)	0.0509 (4)
C11	1.2909 (3)	0.16807 (9)	0.38214 (8)	0.0537 (4)
C12	0.8139 (3)	0.29470 (9)	0.28753 (7)	0.0484 (4)
C13	0.8087 (3)	0.37611 (10)	0.26827 (8)	0.0547 (4)
H13A	0.9214	0.4122	0.2876	0.066*
C14	0.6399 (3)	0.40372 (10)	0.22128 (8)	0.0564 (4)
H14A	0.6392	0.4581	0.2093	0.068*
C15	0.4699 (3)	0.35068 (10)	0.19151 (8)	0.0511 (4)
C16	0.4713 (3)	0.27011 (10)	0.21019 (8)	0.0544 (4)
H16A	0.3585	0.2341	0.1908	0.065*
C17	0.6410 (3)	0.24309 (10)	0.25784 (8)	0.0534 (4)
H17A	0.6391	0.1889	0.2703	0.064*
C18	0.1324 (3)	0.33169 (12)	0.11351 (9)	0.0643 (5)
H18A	0.0257	0.3082	0.1465	0.077*
H18B	0.2131	0.2881	0.0900	0.077*
C19	−0.0167 (4)	0.38315 (14)	0.06586 (11)	0.0864 (7)
H19A	−0.1479	0.3513	0.0461	0.130*
H19B	0.0887	0.4030	0.0317	0.130*
H19C	−0.0865	0.4281	0.0893	0.130*
C20	1.0686 (3)	0.13264 (10)	0.28075 (9)	0.0608 (5)
C21	1.5900 (4)	0.07236 (12)	0.42137 (11)	0.0818 (7)
H21A	1.6516	0.0196	0.4105	0.123*
H21B	1.5285	0.0719	0.4657	0.123*
H21C	1.7217	0.1112	0.4185	0.123*
H2N3	1.747 (5)	0.4641 (15)	0.6750 (13)	0.101 (8)*
H1N3	1.536 (5)	0.5205 (19)	0.6634 (15)	0.129 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0660 (7)	0.0607 (7)	0.0629 (8)	−0.0029 (6)	−0.0309 (6)	0.0055 (6)
O2	0.0944 (9)	0.0481 (6)	0.0765 (9)	0.0129 (6)	−0.0432 (8)	−0.0048 (6)
N1	0.0654 (8)	0.0489 (7)	0.0478 (7)	−0.0002 (6)	−0.0171 (6)	0.0033 (6)
N2	0.1065 (14)	0.0644 (10)	0.0843 (12)	0.0134 (9)	−0.0443 (11)	−0.0191 (9)
N3	0.1089 (16)	0.1055 (16)	0.0794 (13)	0.0313 (13)	−0.0496 (12)	−0.0399 (12)
C1	0.0775 (12)	0.0515 (9)	0.0655 (11)	0.0122 (8)	−0.0303 (9)	−0.0019 (8)
C2	0.0783 (12)	0.0623 (10)	0.0603 (11)	0.0073 (9)	−0.0347 (9)	0.0019 (8)
C3	0.0720 (11)	0.0775 (12)	0.0485 (10)	0.0090 (9)	−0.0192 (9)	−0.0112 (8)
C4	0.0993 (16)	0.1191 (19)	0.0918 (16)	0.0551 (14)	−0.0506 (13)	−0.0563 (15)
C5	0.0796 (13)	0.1055 (16)	0.0750 (14)	0.0393 (12)	−0.0402 (11)	−0.0366 (12)
C6	0.0576 (9)	0.0548 (9)	0.0411 (8)	0.0016 (7)	−0.0128 (7)	0.0017 (7)
C7	0.0555 (9)	0.0513 (8)	0.0431 (8)	−0.0004 (7)	−0.0106 (7)	0.0030 (6)
C8	0.0626 (10)	0.0513 (8)	0.0472 (9)	0.0068 (7)	−0.0148 (7)	−0.0027 (7)
C9	0.0510 (8)	0.0499 (8)	0.0439 (8)	−0.0027 (7)	−0.0108 (7)	0.0037 (6)
C10	0.0586 (9)	0.0466 (8)	0.0468 (8)	−0.0045 (7)	−0.0156 (7)	0.0023 (6)
C11	0.0651 (10)	0.0436 (8)	0.0516 (9)	0.0004 (7)	−0.0162 (8)	0.0048 (7)
C12	0.0505 (8)	0.0499 (8)	0.0442 (8)	0.0006 (7)	−0.0123 (7)	−0.0004 (6)
C13	0.0628 (10)	0.0474 (8)	0.0530 (9)	−0.0030 (7)	−0.0209 (8)	−0.0033 (7)
C14	0.0675 (10)	0.0444 (8)	0.0562 (10)	0.0000 (7)	−0.0212 (8)	0.0020 (7)
C15	0.0523 (8)	0.0531 (8)	0.0471 (9)	0.0016 (7)	−0.0146 (7)	0.0007 (7)
C16	0.0503 (9)	0.0545 (9)	0.0576 (10)	−0.0071 (7)	−0.0172 (7)	0.0012 (7)
C17	0.0543 (9)	0.0487 (8)	0.0568 (9)	−0.0036 (7)	−0.0122 (7)	0.0068 (7)
C18	0.0598 (10)	0.0711 (11)	0.0608 (11)	−0.0038 (8)	−0.0226 (8)	−0.0032 (8)
C19	0.0809 (14)	0.0989 (16)	0.0775 (14)	−0.0139 (12)	−0.0418 (11)	0.0149 (12)
C20	0.0703 (11)	0.0479 (8)	0.0630 (11)	0.0020 (8)	−0.0256 (9)	−0.0007 (8)
C21	0.0986 (15)	0.0603 (11)	0.0843 (14)	0.0193 (10)	−0.0444 (12)	−0.0005 (10)

Geometric parameters (Å, º) top

O1—C15	1.3612 (17)	C9—C10	1.407 (2)
O1—C18	1.4291 (19)	C9—C12	1.485 (2)
O2—C11	1.3502 (19)	C10—C11	1.402 (2)
O2—C21	1.437 (2)	C10—C20	1.427 (2)
N1—C11	1.3114 (19)	C12—C17	1.388 (2)
N1—C7	1.356 (2)	C12—C13	1.399 (2)
N2—C20	1.141 (2)	C13—C14	1.376 (2)
N3—C3	1.377 (2)	C13—H13A	0.9300
N3—H2N3	0.88 (3)	C14—C15	1.393 (2)
N3—H1N3	0.86 (3)	C14—H14A	0.9300
C1—C2	1.380 (2)	C15—C16	1.382 (2)
C1—C6	1.385 (2)	C16—C17	1.385 (2)
C1—H1A	0.9300	C16—H16A	0.9300
C2—C3	1.376 (3)	C17—H17A	0.9300
C2—H2A	0.9300	C18—C19	1.501 (3)
C3—C4	1.376 (3)	C18—H18A	0.9700
C4—C5	1.375 (3)	C18—H18B	0.9700
C4—H4A	0.9300	C19—H19A	0.9600
C5—C6	1.375 (3)	C19—H19B	0.9600
C5—H5A	0.9300	C19—H19C	0.9600
C6—C7	1.473 (2)	C21—H21A	0.9600
C7—C8	1.391 (2)	C21—H21B	0.9600
C8—C9	1.391 (2)	C21—H21C	0.9600
C8—H8A	0.9300

C15—O1—C18	118.42 (13)	O2—C11—C10	115.38 (14)
C11—O2—C21	117.24 (13)	C17—C12—C13	117.46 (14)
C11—N1—C7	117.77 (13)	C17—C12—C9	122.12 (14)
C3—N3—H2N3	119.3 (17)	C13—C12—C9	120.42 (13)
C3—N3—H1N3	117 (2)	C14—C13—C12	121.20 (14)
H2N3—N3—H1N3	117 (3)	C14—C13—H13A	119.4
C2—C1—C6	121.82 (17)	C12—C13—H13A	119.4
C2—C1—H1A	119.1	C13—C14—C15	120.40 (15)
C6—C1—H1A	119.1	C13—C14—H14A	119.8
C3—C2—C1	121.18 (16)	C15—C14—H14A	119.8
C3—C2—H2A	119.4	O1—C15—C16	124.59 (14)
C1—C2—H2A	119.4	O1—C15—C14	116.19 (14)
C2—C3—C4	117.04 (17)	C16—C15—C14	119.22 (14)
C2—C3—N3	121.22 (18)	C15—C16—C17	119.88 (14)
C4—C3—N3	121.7 (2)	C15—C16—H16A	120.1
C5—C4—C3	121.77 (19)	C17—C16—H16A	120.1
C5—C4—H4A	119.1	C16—C17—C12	121.83 (15)
C3—C4—H4A	119.1	C16—C17—H17A	119.1
C6—C5—C4	121.70 (17)	C12—C17—H17A	119.1
C6—C5—H5A	119.1	O1—C18—C19	107.14 (15)
C4—C5—H5A	119.1	O1—C18—H18A	110.3
C5—C6—C1	116.47 (15)	C19—C18—H18A	110.3
C5—C6—C7	123.06 (15)	O1—C18—H18B	110.3
C1—C6—C7	120.46 (15)	C19—C18—H18B	110.3
N1—C7—C8	121.12 (14)	H18A—C18—H18B	108.5
N1—C7—C6	115.86 (13)	C18—C19—H19A	109.5
C8—C7—C6	123.02 (14)	C18—C19—H19B	109.5
C9—C8—C7	121.57 (15)	H19A—C19—H19B	109.5
C9—C8—H8A	119.2	C18—C19—H19C	109.5
C7—C8—H8A	119.2	H19A—C19—H19C	109.5
C8—C9—C10	116.51 (13)	H19B—C19—H19C	109.5
C8—C9—C12	121.09 (14)	N2—C20—C10	177.0 (2)
C10—C9—C12	122.38 (13)	O2—C21—H21A	109.5
C11—C10—C9	118.00 (14)	O2—C21—H21B	109.5
C11—C10—C20	117.27 (14)	H21A—C21—H21B	109.5
C9—C10—C20	124.46 (13)	O2—C21—H21C	109.5
N1—C11—O2	119.58 (13)	H21A—C21—H21C	109.5
N1—C11—C10	125.03 (15)	H21B—C21—H21C	109.5

C6—C1—C2—C3	−0.5 (3)	C7—N1—C11—C10	0.1 (3)
C1—C2—C3—C4	1.2 (3)	C21—O2—C11—N1	−3.0 (3)
C1—C2—C3—N3	−176.7 (2)	C21—O2—C11—C10	176.03 (17)
C2—C3—C4—C5	−1.3 (4)	C9—C10—C11—N1	0.0 (3)
N3—C3—C4—C5	176.6 (3)	C20—C10—C11—N1	174.15 (17)
C3—C4—C5—C6	0.7 (5)	C9—C10—C11—O2	−179.00 (15)
C4—C5—C6—C1	0.1 (4)	C20—C10—C11—O2	−4.8 (2)
C4—C5—C6—C7	179.0 (2)	C8—C9—C12—C17	−146.49 (17)
C2—C1—C6—C5	−0.2 (3)	C10—C9—C12—C17	35.4 (2)
C2—C1—C6—C7	−179.14 (17)	C8—C9—C12—C13	34.1 (2)
C11—N1—C7—C8	0.3 (2)	C10—C9—C12—C13	−144.01 (17)
C11—N1—C7—C6	−179.60 (15)	C17—C12—C13—C14	−0.5 (3)
C5—C6—C7—N1	−165.10 (19)	C9—C12—C13—C14	178.94 (16)
C1—C6—C7—N1	13.8 (2)	C12—C13—C14—C15	−0.2 (3)
C5—C6—C7—C8	15.0 (3)	C18—O1—C15—C16	1.8 (3)
C1—C6—C7—C8	−166.12 (17)	C18—O1—C15—C14	−178.89 (15)
N1—C7—C8—C9	−0.8 (3)	C13—C14—C15—O1	−178.79 (16)
C6—C7—C8—C9	179.16 (16)	C13—C14—C15—C16	0.6 (3)
C7—C8—C9—C10	0.8 (2)	O1—C15—C16—C17	179.15 (16)
C7—C8—C9—C12	−177.43 (15)	C14—C15—C16—C17	−0.2 (3)
C8—C9—C10—C11	−0.4 (2)	C15—C16—C17—C12	−0.6 (3)
C12—C9—C10—C11	177.79 (15)	C13—C12—C17—C16	1.0 (3)
C8—C9—C10—C20	−174.09 (17)	C9—C12—C17—C16	−178.51 (16)
C12—C9—C10—C20	4.1 (3)	C15—O1—C18—C19	178.70 (16)
C7—N1—C11—O2	178.99 (16)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H2N3···N2ⁱ	0.88 (3)	2.20 (3)	3.084 (3)	177 (2)
C21—H21A···O1ⁱⁱ	0.96	2.52	3.439 (2)	160
C18—H18A···Cgⁱⁱⁱ	0.96	2.84	3.7135 (18)	151

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₉N₃O₂
M_r	345.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	5.3924 (2), 16.5111 (5), 20.1415 (6)
β (°)	91.315 (2)
V (Å³)	1792.82 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.54 × 0.25 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.956, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	17814, 5216, 3013
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.159, 1.03
No. of reflections	5216
No. of parameters	245
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H2N3···N2ⁱ	0.88 (3)	2.20 (3)	3.084 (3)	177 (2)
C21—H21A···O1ⁱⁱ	0.96	2.52	3.439 (2)	160
C18—H18A···Cgⁱⁱⁱ	0.96	2.84	3.7135 (18)	151

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

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§Additional correspondence author, e-mail: hkfun@usm.my. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

TS thanks the Thailand Research Fund through the Royal Golden Jubilee PhD Program and the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education, Ministry of Education, Thailand for financial support. The authors thank the Thailand Research Fund (grant No. RSA 5280033), Prince of Songkla University and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

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Volume 68| Part 9| September 2012| Pages o2812-o2813

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