6-Meth­oxy-4-(2,4,5-tri­meth­oxy­phen­yl)-2,2′-bi­pyridine-5-carbo­nitrile

Chantrapromma, S.; Suwunwong, T.; Ruanwas, P.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536813023891

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Pages o1500-o1501

doi:10.1107/S1600536813023891

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6-Methoxy-4-(2,4,5-trimethoxyphenyl)-2,2′-bipyridine-5-carbonitrile

Suchada Chantrapromma,^a ^*‡ Thitipone Suwunwong,^a Pumsak Ruanwas,^a Ching Kheng Quah ^b and Hoong-Kun Fun ^b §

^aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 2 August 2013; accepted 26 August 2013; online 4 September 2013)

In the title 3-cyanopyridine derivative, C₂₁H₁₉N₃O₄, the 3-cyano-substituted pyridine ring forms dihedral angles of 2.35 (5) and 41.60 (5)° with the unsubstituted pyridine and 2,4,5-trimethoxy-substituted benzene rings, respectively. The dihedral angle between the unsubstituted pyridine and benzene rings is 39.84 (5)°. The methoxy groups form C_methyl—O—C—(C,N) torsion angles in the range 0.80 (15)–11.45 (15)°. In the crystal, molecules related by 2₁ screw axes are linked by weak C—H⋯N hydrogen bonds along [010]. In addition, weak C—H⋯π interactions and π–π stacking interactions between pyridine rings, with a centroid–centroid distance of 3.6448 (6) Å, are observed.

Related literature

For the synthesis and applications of 3-cyanopyridine derivatives, see: Al-Jaber et al. (2012 ); Brandt et al. (2010 ); El-Sayed et al. (2011 ); Ji et al. (2007 ); Kim et al. (2005 ); Koner et al. (2012 ); Suwunwong et al. (2011 ); Zhou et al. (2006 ). For related structures, see: Chantrapromma et al. (2010 ); Suwunwong et al. (2012 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₁₉N₃O₄
M_r = 377.39
Monoclinic, P 2₁ /c
a = 14.9967 (3) Å
b = 7.4039 (2) Å
c = 17.5795 (4) Å
β = 114.080 (1)°
V = 1782.06 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.60 × 0.29 × 0.23 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.943, T_max = 0.977
20323 measured reflections
5182 independent reflections
4386 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.116
S = 1.03
5182 reflections
257 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg₃ is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20C⋯N3ⁱ	0.98	2.59	3.3774 (17)	138
C1—H1A⋯Cg3ⁱⁱ	0.95	2.89	3.7062 (13)	145
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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, PLATON (Spek, 2009 ), Mercury (Macrae et al., 2006 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813023891/lh5641sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813023891/lh5641Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813023891/lh5641Isup3.cml

checkCIF report

Comment top

3-Cyanopyridine derivatives have been reported for their wide range of applications such as in antimicrobial, analgesic, anti-hyperglycemic, antiproliferative and antitumor activities (Brandt et al., 2010; El-Sayed et al., 2011; Ji et al., 2007; Kim et al., 2005), as well as in usage as fluorescence materials (Koner et al., 2012). There are several methods to synthesize substituted 3-cyanopyridine derivatives including by condensation of α,β-unsaturated ketones and malononitrile (Al-Jaber et al., 2012; Zhou et al., 2006). Our research is aimed at the synthesis and preliminary fluorescent and antibacterial screening of the 3-cyanopyridine derivatives. The title compound (I) was synthesized and was found to exhibit fluorescence property which will be reported elsewhere together with the other related compounds. Herein the crystal structure of (I) was reported.

The title compound (I), C₂₁H₁₉N₃O₄ is a non-planar molecule (Fig. 1) in which the 3-cyano-substituted pyridine ring is approximately co-planar with the unsubstituted pyridine ring and inclined to the 2,4,5-trimethoxy-substituted ring with dihedral angles of 2.35 (5) and 41.60 (5)°, respectively. The dihedral angle between the unsubstituted pyridine and benzene rings is 39.84 (5)°. For the 2,4,5-trimethoxyphenyl moiety, the two substituted methoxy groups at ortho and meta positions are slightly twisted with the attached benzene ring with torsion angles C19–O2–C12–C13 = -11.45 (15)° and C21–O4–C15–C16 = -8.11 (16)° whereas the para methoxy group is essentially co-planar with a dihedral angle of C20–O3–C14–C13 = -0.80 (15)°. In addition, the methoxy group of the 3-cyanopyridine group is also essentially co-planar with the pyridine ring as indicated by the torsion angle C17–O1–C10–N2 = 6.18 (14)°. The bond distances agree with the literature values (Allen et al., 1987) and are comparable with those found in the related structures (Chantrapromma et al., 2010; Suwunwong et al., 2012).

In the crystal (Fig. 2), molecules related by 2₁ screw axes are linked by weak C—H···N interactions (Table 1) to form helical chains. The crystal is further stabilized by weak C—H···π interactions (Table 1) and π–π interaction with the Cg₁···Cg₂ⁱⁱⁱ distance of 3.6448 (6) Å (iii = -x, 1 - y, -z); Cg₁ and Cg₂ are the centroids of N1/C1–C5 and N2/C6–C10 pyridine rings, respectively.

Related literature top

For the synthesis and applications of 3-cyanopyridine derivatives, see: Al-Jaber et al. (2012); Brandt et al. (2010); El-Sayed et al. (2011); Ji et al. (2007); Kim et al. (2005); Koner et al. (2012); Suwunwong et al. (2011); Zhou et al. (2006). For related structures, see: Chantrapromma et al. (2010); Suwunwong et al. (2012). For standard bond-length data, see: Allen et al. (1987).

Experimental top

The title compound (I) was synthesized by stirring a solution of (E)-1-(pyridin-2-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one (Suwunwong et al., 2011) (0.30 g, 1 mmol) in 10 ml of methanol with a freshly prepared sodium methoxide (1 mmol of sodium in 20 ml of methanol). Excess malononitrile (0.13 g, 2 mmol) was then added with continuous stirring at room temperature until the precipitate was separated out. The resulting solid was filtered and washed with hexane. Colorless block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystallized from ethanol/methanol (1:1 v/v) by the slow evaporation of the solvent at room temperature after several days, Mp. 506–507 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), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

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 approximately along the a axis. Weak C—H···N interactions are shown as dashed lines. For clarity, only H atoms involved in hydrogen bonds are shown.

6-Methoxy-4-(2,4,5-trimethoxyphenyl)-2,2'-bipyridine-5-carbonitrile top

Crystal data top

C₂₁H₁₉N₃O₄	F(000) = 792
M_r = 377.39	D_x = 1.407 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 506–507 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.9967 (3) Å	Cell parameters from 5182 reflections
b = 7.4039 (2) Å	θ = 2.4–30.0°
c = 17.5795 (4) Å	µ = 0.10 mm⁻¹
β = 114.080 (1)°	T = 100 K
V = 1782.06 (7) Å³	Block, colorless
Z = 4	0.60 × 0.29 × 0.23 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	5182 independent reflections
Radiation source: sealed tube	4386 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −21→21
T_min = 0.943, T_max = 0.977	k = −10→10
20323 measured reflections	l = −22→24

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0629P)² + 0.5246P] where P = (F_o² + 2F_c²)/3
5182 reflections	(Δ/σ)_max = 0.001
257 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₁H₁₉N₃O₄	V = 1782.06 (7) Å³
M_r = 377.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.9967 (3) Å	µ = 0.10 mm⁻¹
b = 7.4039 (2) Å	T = 100 K
c = 17.5795 (4) Å	0.60 × 0.29 × 0.23 mm
β = 114.080 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5182 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4386 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.977	R_int = 0.030
20323 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.03	Δρ_max = 0.40 e Å⁻³
5182 reflections	Δρ_min = −0.31 e Å⁻³
257 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.08878 (6)	0.11337 (11)	−0.09750 (5)	0.01663 (17)
O2	0.21018 (6)	0.46941 (10)	0.24541 (5)	0.01852 (17)
O3	0.48961 (5)	0.12019 (10)	0.42643 (5)	0.01676 (17)
O4	0.44854 (6)	−0.13384 (11)	0.31664 (5)	0.02014 (18)
N1	−0.10990 (7)	0.40828 (13)	0.10405 (6)	0.01619 (19)
N2	−0.00502 (6)	0.22953 (12)	−0.03257 (5)	0.01373 (18)
N3	0.32255 (7)	0.04540 (15)	0.03661 (7)	0.0231 (2)
C1	−0.19408 (8)	0.48087 (15)	0.09883 (7)	0.0174 (2)
H1A	−0.1982	0.5191	0.1489	0.021*
C2	−0.27560 (8)	0.50345 (15)	0.02446 (7)	0.0176 (2)
H2A	−0.3340	0.5543	0.0239	0.021*
C3	−0.26961 (8)	0.44990 (16)	−0.04895 (7)	0.0187 (2)
H3A	−0.3240	0.4640	−0.1009	0.022*
C4	−0.18290 (8)	0.37531 (15)	−0.04529 (7)	0.0160 (2)
H4A	−0.1768	0.3381	−0.0947	0.019*
C5	−0.10496 (7)	0.35617 (13)	0.03249 (6)	0.01291 (19)
C6	−0.01002 (7)	0.27984 (13)	0.03969 (6)	0.01266 (19)
C7	0.06802 (7)	0.26430 (14)	0.11670 (6)	0.0139 (2)
H7A	0.0605	0.2991	0.1658	0.017*
C8	0.15792 (7)	0.19739 (13)	0.12237 (6)	0.01287 (19)
C9	0.16324 (7)	0.14605 (14)	0.04744 (6)	0.01298 (19)
C10	0.07884 (7)	0.16495 (14)	−0.02772 (6)	0.01309 (19)
C11	0.24309 (7)	0.18194 (14)	0.20364 (6)	0.01303 (19)
C12	0.26734 (7)	0.31794 (14)	0.26440 (6)	0.0139 (2)
C13	0.34940 (7)	0.30003 (14)	0.33993 (6)	0.0140 (2)
H13A	0.3648	0.3925	0.3808	0.017*
C14	0.40836 (7)	0.14785 (14)	0.35544 (6)	0.01330 (19)
C15	0.38513 (7)	0.00954 (14)	0.29540 (7)	0.0144 (2)
C16	0.30335 (7)	0.02751 (14)	0.22149 (6)	0.01395 (19)
H16A	0.2872	−0.0669	0.1815	0.017*
C17	0.00747 (8)	0.15056 (17)	−0.17547 (7)	0.0197 (2)
H17A	0.0223	0.1065	−0.2216	0.030*
H17B	−0.0042	0.2811	−0.1813	0.030*
H17C	−0.0510	0.0894	−0.1766	0.030*
C18	0.25207 (8)	0.08862 (14)	0.04235 (7)	0.0156 (2)
C19	0.22509 (8)	0.59686 (15)	0.31086 (7)	0.0179 (2)
H19A	0.1754	0.6919	0.2905	0.027*
H19B	0.2901	0.6508	0.3286	0.027*
H19C	0.2199	0.5350	0.3582	0.027*
C20	0.51581 (8)	0.25983 (15)	0.48834 (7)	0.0176 (2)
H20A	0.5748	0.2240	0.5366	0.026*
H20B	0.4622	0.2786	0.5057	0.026*
H20C	0.5284	0.3722	0.4649	0.026*
C21	0.43561 (9)	−0.26391 (16)	0.25325 (8)	0.0222 (2)
H21A	0.4884	−0.3531	0.2740	0.033*
H21B	0.4369	−0.2032	0.2042	0.033*
H21C	0.3727	−0.3249	0.2380	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0182 (4)	0.0217 (4)	0.0112 (3)	0.0019 (3)	0.0073 (3)	−0.0016 (3)
O2	0.0206 (4)	0.0147 (4)	0.0154 (4)	0.0058 (3)	0.0025 (3)	−0.0031 (3)
O3	0.0152 (3)	0.0164 (4)	0.0146 (4)	0.0022 (3)	0.0019 (3)	−0.0016 (3)
O4	0.0214 (4)	0.0175 (4)	0.0186 (4)	0.0082 (3)	0.0052 (3)	−0.0020 (3)
N1	0.0170 (4)	0.0174 (4)	0.0164 (4)	0.0018 (3)	0.0091 (3)	0.0008 (3)
N2	0.0147 (4)	0.0135 (4)	0.0135 (4)	−0.0011 (3)	0.0063 (3)	−0.0006 (3)
N3	0.0234 (5)	0.0244 (5)	0.0266 (5)	0.0047 (4)	0.0154 (4)	0.0035 (4)
C1	0.0202 (5)	0.0171 (5)	0.0187 (5)	0.0027 (4)	0.0119 (4)	0.0012 (4)
C2	0.0152 (5)	0.0150 (5)	0.0248 (6)	0.0012 (4)	0.0104 (4)	0.0006 (4)
C3	0.0143 (4)	0.0197 (5)	0.0196 (5)	0.0000 (4)	0.0043 (4)	−0.0017 (4)
C4	0.0160 (4)	0.0168 (5)	0.0152 (5)	−0.0007 (4)	0.0062 (4)	−0.0025 (4)
C5	0.0141 (4)	0.0111 (4)	0.0153 (5)	−0.0013 (3)	0.0077 (4)	0.0000 (3)
C6	0.0142 (4)	0.0110 (4)	0.0144 (5)	−0.0008 (3)	0.0075 (4)	−0.0004 (3)
C7	0.0150 (4)	0.0148 (4)	0.0135 (5)	−0.0001 (4)	0.0074 (4)	−0.0011 (3)
C8	0.0141 (4)	0.0120 (4)	0.0129 (4)	−0.0006 (3)	0.0059 (4)	−0.0001 (3)
C9	0.0139 (4)	0.0122 (4)	0.0142 (5)	0.0003 (3)	0.0072 (4)	−0.0002 (3)
C10	0.0167 (4)	0.0119 (4)	0.0120 (4)	−0.0006 (3)	0.0073 (4)	−0.0005 (3)
C11	0.0128 (4)	0.0144 (5)	0.0125 (4)	0.0001 (3)	0.0058 (3)	0.0000 (3)
C12	0.0140 (4)	0.0135 (5)	0.0146 (5)	0.0013 (4)	0.0061 (4)	0.0005 (4)
C13	0.0152 (4)	0.0136 (5)	0.0134 (5)	0.0001 (4)	0.0059 (4)	−0.0011 (4)
C14	0.0123 (4)	0.0152 (5)	0.0124 (4)	−0.0005 (3)	0.0051 (4)	0.0014 (3)
C15	0.0151 (4)	0.0130 (5)	0.0167 (5)	0.0022 (4)	0.0083 (4)	0.0010 (4)
C16	0.0158 (4)	0.0136 (5)	0.0135 (5)	−0.0004 (4)	0.0071 (4)	−0.0016 (4)
C17	0.0215 (5)	0.0256 (6)	0.0107 (5)	−0.0002 (4)	0.0051 (4)	0.0000 (4)
C18	0.0183 (5)	0.0152 (5)	0.0143 (5)	0.0003 (4)	0.0078 (4)	0.0011 (4)
C19	0.0188 (5)	0.0158 (5)	0.0172 (5)	0.0028 (4)	0.0055 (4)	−0.0041 (4)
C20	0.0156 (5)	0.0177 (5)	0.0162 (5)	−0.0018 (4)	0.0030 (4)	−0.0029 (4)
C21	0.0273 (6)	0.0188 (5)	0.0225 (6)	0.0059 (4)	0.0122 (5)	−0.0033 (4)

Geometric parameters (Å, º) top

O1—C10	1.3499 (12)	C8—C9	1.4041 (14)
O1—C17	1.4415 (13)	C8—C11	1.4820 (13)
O2—C12	1.3676 (12)	C9—C10	1.4152 (13)
O2—C19	1.4332 (13)	C9—C18	1.4355 (14)
O3—C14	1.3576 (12)	C11—C12	1.4036 (14)
O3—C20	1.4349 (13)	C11—C16	1.4110 (14)
O4—C15	1.3715 (12)	C12—C13	1.4006 (14)
O4—C21	1.4250 (14)	C13—C14	1.3888 (14)
N1—C1	1.3403 (14)	C13—H13A	0.9500
N1—C5	1.3465 (13)	C14—C15	1.4085 (14)
N2—C10	1.3152 (13)	C15—C16	1.3819 (14)
N2—C6	1.3549 (13)	C16—H16A	0.9500
N3—C18	1.1476 (14)	C17—H17A	0.9800
C1—C2	1.3883 (15)	C17—H17B	0.9800
C1—H1A	0.9500	C17—H17C	0.9800
C2—C3	1.3876 (16)	C19—H19A	0.9800
C2—H2A	0.9500	C19—H19B	0.9800
C3—C4	1.3899 (15)	C19—H19C	0.9800
C3—H3A	0.9500	C20—H20A	0.9800
C4—C5	1.3970 (14)	C20—H20B	0.9800
C4—H4A	0.9500	C20—H20C	0.9800
C5—C6	1.4885 (14)	C21—H21A	0.9800
C6—C7	1.3866 (14)	C21—H21B	0.9800
C7—C8	1.4013 (14)	C21—H21C	0.9800
C7—H7A	0.9500

C10—O1—C17	116.48 (8)	O2—C12—C11	117.43 (9)
C12—O2—C19	117.84 (8)	C13—C12—C11	120.54 (9)
C14—O3—C20	116.99 (8)	C14—C13—C12	120.38 (9)
C15—O4—C21	116.88 (8)	C14—C13—H13A	119.8
C1—N1—C5	117.40 (9)	C12—C13—H13A	119.8
C10—N2—C6	117.15 (9)	O3—C14—C13	124.30 (9)
N1—C1—C2	123.76 (10)	O3—C14—C15	115.72 (9)
N1—C1—H1A	118.1	C13—C14—C15	119.98 (9)
C2—C1—H1A	118.1	O4—C15—C16	125.54 (9)
C3—C2—C1	118.37 (10)	O4—C15—C14	115.26 (9)
C3—C2—H2A	120.8	C16—C15—C14	119.20 (9)
C1—C2—H2A	120.8	C15—C16—C11	121.96 (9)
C2—C3—C4	119.00 (10)	C15—C16—H16A	119.0
C2—C3—H3A	120.5	C11—C16—H16A	119.0
C4—C3—H3A	120.5	O1—C17—H17A	109.5
C3—C4—C5	118.62 (10)	O1—C17—H17B	109.5
C3—C4—H4A	120.7	H17A—C17—H17B	109.5
C5—C4—H4A	120.7	O1—C17—H17C	109.5
N1—C5—C4	122.85 (9)	H17A—C17—H17C	109.5
N1—C5—C6	116.40 (9)	H17B—C17—H17C	109.5
C4—C5—C6	120.73 (9)	N3—C18—C9	178.32 (12)
N2—C6—C7	123.03 (9)	O2—C19—H19A	109.5
N2—C6—C5	116.20 (9)	O2—C19—H19B	109.5
C7—C6—C5	120.77 (9)	H19A—C19—H19B	109.5
C6—C7—C8	120.21 (9)	O2—C19—H19C	109.5
C6—C7—H7A	119.9	H19A—C19—H19C	109.5
C8—C7—H7A	119.9	H19B—C19—H19C	109.5
C7—C8—C9	116.76 (9)	O3—C20—H20A	109.5
C7—C8—C11	121.44 (9)	O3—C20—H20B	109.5
C9—C8—C11	121.80 (9)	H20A—C20—H20B	109.5
C8—C9—C10	118.53 (9)	O3—C20—H20C	109.5
C8—C9—C18	123.23 (9)	H20A—C20—H20C	109.5
C10—C9—C18	118.06 (9)	H20B—C20—H20C	109.5
N2—C10—O1	120.08 (9)	O4—C21—H21A	109.5
N2—C10—C9	124.32 (9)	O4—C21—H21B	109.5
O1—C10—C9	115.60 (9)	H21A—C21—H21B	109.5
C12—C11—C16	117.94 (9)	O4—C21—H21C	109.5
C12—C11—C8	122.14 (9)	H21A—C21—H21C	109.5
C16—C11—C8	119.92 (9)	H21B—C21—H21C	109.5
O2—C12—C13	121.99 (9)

C5—N1—C1—C2	0.52 (16)	C8—C9—C10—O1	179.95 (9)
N1—C1—C2—C3	−0.76 (17)	C18—C9—C10—O1	4.76 (14)
C1—C2—C3—C4	0.29 (16)	C7—C8—C11—C12	−42.34 (15)
C2—C3—C4—C5	0.33 (16)	C9—C8—C11—C12	137.61 (11)
C1—N1—C5—C4	0.16 (15)	C7—C8—C11—C16	138.34 (10)
C1—N1—C5—C6	178.65 (9)	C9—C8—C11—C16	−41.70 (14)
C3—C4—C5—N1	−0.58 (16)	C19—O2—C12—C13	−11.45 (15)
C3—C4—C5—C6	−179.01 (10)	C19—O2—C12—C11	171.00 (9)
C10—N2—C6—C7	−0.63 (15)	C16—C11—C12—O2	178.04 (9)
C10—N2—C6—C5	178.74 (9)	C8—C11—C12—O2	−1.29 (15)
N1—C5—C6—N2	−179.26 (9)	C16—C11—C12—C13	0.46 (15)
C4—C5—C6—N2	−0.74 (14)	C8—C11—C12—C13	−178.87 (9)
N1—C5—C6—C7	0.12 (14)	O2—C12—C13—C14	−176.97 (10)
C4—C5—C6—C7	178.65 (10)	C11—C12—C13—C14	0.50 (16)
N2—C6—C7—C8	1.31 (16)	C20—O3—C14—C13	−0.80 (15)
C5—C6—C7—C8	−178.03 (9)	C20—O3—C14—C15	179.26 (9)
C6—C7—C8—C9	−0.94 (15)	C12—C13—C14—O3	179.36 (10)
C6—C7—C8—C11	179.02 (9)	C12—C13—C14—C15	−0.70 (16)
C7—C8—C9—C10	0.02 (14)	C21—O4—C15—C16	8.11 (16)
C11—C8—C9—C10	−179.94 (9)	C21—O4—C15—C14	−171.38 (10)
C7—C8—C9—C18	174.95 (9)	O3—C14—C15—O4	−0.60 (14)
C11—C8—C9—C18	−5.01 (16)	C13—C14—C15—O4	179.45 (9)
C6—N2—C10—O1	−179.62 (9)	O3—C14—C15—C16	179.88 (9)
C6—N2—C10—C9	−0.37 (15)	C13—C14—C15—C16	−0.07 (15)
C17—O1—C10—N2	6.18 (14)	O4—C15—C16—C11	−178.40 (10)
C17—O1—C10—C9	−173.13 (9)	C14—C15—C16—C11	1.06 (16)
C8—C9—C10—N2	0.67 (16)	C12—C11—C16—C15	−1.25 (15)
C18—C9—C10—N2	−174.53 (10)	C8—C11—C16—C15	178.09 (10)

Hydrogen-bond geometry (Å, º) top

Cg₃ is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20C···N3ⁱ	0.98	2.59	3.3774 (17)	138
C1—H1A···Cg3ⁱⁱ	0.95	2.89	3.7062 (13)	145

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

Hydrogen-bond geometry (Å, º) top

Cg₃ is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20C···N3ⁱ	0.98	2.59	3.3774 (17)	138
C1—H1A···Cg3ⁱⁱ	0.95	2.89	3.7062 (13)	145

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

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

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

Acknowledgements

TS and SC thank the Thailand Research Fund through the Royal Golden Jubilee PhD Program (grant No. PHD/0257/2553) for financial support. The authors thank the Universiti Sains Malaysia for the APEX DE2012 grant No. 1002/PFIZIK/910323.

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Volume 69| Part 10| October 2013| Pages o1500-o1501

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