6-(4-Amino­phen­yl)-2-meth­oxy-4-phenyl­nicotino­nitrile

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

doi:10.1107/S1600536813031437

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages o1816-o1817

doi:10.1107/S1600536813031437

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6-(4-Aminophenyl)-2-methoxy-4-phenylnicotinonitrile

Thitipone Suwunwong,^a Suchada Chantrapromma,^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 8 November 2013; accepted 18 November 2013; online 23 November 2013)

In the structure of the title nicotinonitrile derivative, C₁₉H₁₅N₃O, the pyridine ring makes dihedral angles of 11.50 (7) and 43.36 (8)° with the 4-aminophenyl and phenyl rings, respectively, and the dihedral angle between the phenyl rings is 36.28°. In the crystal, molecules are linked by N—H⋯N hydrogen bonds into wave-like sheets parallel to (10-2). These sheets are stacked by π–π interactions between the 4-aminophenyl rings of adjacent sheets, with centroid–centroid distances of 3.7499 (9) Å. C—H⋯π interactions are also present.

CCDC reference: 972405

Related literature

For the synthesis and applications of nicotinonitrile 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 ); Raghukumar et al. (2003 ); Zhou et al. (2006 ). For bond-length data, see: Allen et al. (1987 ). For related structures, see: Chantrapromma et al. (2013 ); Suwunwong et al. (2012 , 2013 ).

Experimental

Crystal data

C₁₉H₁₅N₃O
M_r = 301.34
Monoclinic, P 2₁ /c
a = 10.9448 (12) Å
b = 18.960 (2) Å
c = 7.4738 (8) Å
β = 94.743 (2)°
V = 1545.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.56 × 0.17 × 0.06 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.955, T_max = 0.995
14200 measured reflections
3696 independent reflections
2689 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.143
S = 1.07
3696 reflections
217 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2N1⋯N3ⁱ	0.915 (19)	2.338 (19)	3.2416 (18)	169.5 (19)
N1—H1N1⋯N3ⁱⁱ	0.91 (2)	2.28 (2)	3.1773 (19)	168 (2)
C11—H11A⋯Cg3ⁱⁱⁱ	0.95	2.87	3.7667 (17)	158
C19—H19C⋯Cg2^iv	0.98	2.69	3.5156 (17)	142
Symmetry codes: (i) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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

CCDC reference: 972405

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813031437/sj5368sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813031437/sj5368Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813031437/sj5368Isup3.cml

checkCIF report

Comment top

Nicotinonitrile derivatives are substituted pyridines synthesized from the condensation of α,β-unsaturated ketones with malononitrile (Al-Jaber et al., 2012; Zhou et al., 2006). They have a wide range of bioactivities including 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). Nicotinonitriles also find applications as non-linear optical (Raghukumar et al., 2003) and fluorescent materials (Koner et al., 2012). Continuing our ongoing research on fluorescent materials (Chantrapromma et al., 2013; Suwunwong et al., 2012; 2013), the title compound (I) was synthesized and its fluorescent properties were studied. Our results found that (I) possesses significant fluorescent properties that will be discussed elsewhere, together with those of other closely related compounds. Herein the crystal structure of (I) is reported.

The title compound (I), C₁₉H₁₅N₃O, is a non-planar molecule (Fig. 1). The pyridine ring makes dihedral angles of 11.50 (7)° and 43.36 (8)° with the 4-aminophenyl and phenyl rings, respectively, and the dihedral angle between the two phenyl rings is 36.28°. The methoxy group lies in the plane of the pyridine ring with an rms deviation of 0.0102 (1) Å for the eight non-H atoms (C7–C9/C16–C17/C19/N2/O1) and the torsion angle C19–O1–C16–N2 = -1.2 (2)°. The cyano group is also roughly co-planar with the pyridine ring with an rms deviation of 0.0406 (1) Å from the ring plane. The bond distances in (I) agree with the literature values (Allen et al., 1987) and are comparable to those found in closely related structures (Chantrapromma et al., 2013 and Suwunwong et al., 2012; 2013).

In the crystal structure (Fig. 2), molecules are linked by intermolecular N—H···N hydrogen bonds (Table 1) forming screw chains. These chains are further linked by N—H···N hydrogen bonds into a two dimensional structure as wave-like sheets parallel to the (1 0 - 2) plane (Fig. 3). These sheets are stacked by π···π interactions between 4-aminophenyl rings of the adjacent sheets with Cg₁···Cg₁^{iii, iv} distances of 3.7499 (9) Å; Cg₁ is the centroid of the N2/C7–C9/C16–C17 pyridine ring. The crystal is further stabilized by C–H···π interactions (Table 1).

Related literature top

For the synthesis and applications of nicotinonitrile 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); Raghukumar et al. (2003); Zhou et al. (2006). For bond-length data, see: Allen et al. (1987). For related structures, see: Chantrapromma et al. (2013); Suwunwong et al. (2012, 2013).

Experimental top

The title compound (I) was synthesized by stirring a solution of (E)-1-(4-aminophenyl)-3-phenylprop-2-en-1-one (0.22 g, 1 mmol) in methanol (10 ml) with freshly prepared sodium methoxide (1.0 mmol of sodium in 20 ml of methanol). An excess of malononitrile (0.13 g, 2 mmol) was then added with continuous stirring at room temperature until a precipitate was obtained. The resulting solid was filtered. Yellow plate-shaped single crystals of the title compound suitable for X-ray structure determination was recrystallized from ethanol/methanol (1:1 v/v) by slow evaporation of the solvent at room temperature over several days. Mp. 475–476 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound viewed approximately along the c axis. N—H···N hydrogen bonds are shown as dashed lines.
	Fig. 3. Wave-like sheets of the title compound viewed approximately along the a axis. N—H···N hydrogen bonds are shown as dashed lines.

6-(4-Aminophenyl)-2-methoxy-4-phenylnicotinonitrile top

Crystal data top

C₁₉H₁₅N₃O	F(000) = 632
M_r = 301.34	D_x = 1.295 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 475–476 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.9448 (12) Å	Cell parameters from 3696 reflections
b = 18.960 (2) Å	θ = 2.2–28.0°
c = 7.4738 (8) Å	µ = 0.08 mm⁻¹
β = 94.743 (2)°	T = 100 K
V = 1545.6 (3) Å³	Plate, yellow
Z = 4	0.56 × 0.17 × 0.06 mm

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	3696 independent reflections
Radiation source: sealed tube	2689 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ϕ and ω scans	θ_max = 28.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
T_min = 0.955, T_max = 0.995	k = −24→25
14200 measured reflections	l = −9→9

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: inferred from neighbouring sites
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0815P)² + 0.0098P] where P = (F_o² + 2F_c²)/3
3696 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₉H₁₅N₃O	V = 1545.6 (3) Å³
M_r = 301.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9448 (12) Å	µ = 0.08 mm⁻¹
b = 18.960 (2) Å	T = 100 K
c = 7.4738 (8) Å	0.56 × 0.17 × 0.06 mm
β = 94.743 (2)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	3696 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2689 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.995	R_int = 0.051
14200 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.30 e Å⁻³
3696 reflections	Δρ_min = −0.28 e Å⁻³
217 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	0.41334 (9)	0.11886 (5)	0.32484 (15)	0.0232 (3)
N1	0.87443 (12)	0.47258 (7)	0.5990 (2)	0.0275 (3)
H2N1	0.9480 (17)	0.4498 (10)	0.619 (3)	0.036 (5)*
H1N1	0.8776 (17)	0.5170 (11)	0.554 (3)	0.043 (6)*
N2	0.48483 (11)	0.23181 (6)	0.37739 (17)	0.0197 (3)
N3	0.12753 (11)	0.11690 (6)	0.1173 (2)	0.0262 (3)
C1	0.56914 (12)	0.34757 (7)	0.4295 (2)	0.0188 (3)
C2	0.56860 (13)	0.42059 (7)	0.4009 (2)	0.0211 (3)
H2A	0.4974	0.4421	0.3435	0.025*
C3	0.66877 (13)	0.46216 (7)	0.4540 (2)	0.0222 (3)
H3A	0.6659	0.5115	0.4320	0.027*
C4	0.77484 (13)	0.43173 (7)	0.5405 (2)	0.0211 (3)
C5	0.77592 (13)	0.35885 (8)	0.5715 (2)	0.0231 (3)
H5A	0.8465	0.3374	0.6310	0.028*
C6	0.67552 (13)	0.31784 (7)	0.5163 (2)	0.0218 (3)
H6A	0.6785	0.2684	0.5375	0.026*
C7	0.46428 (12)	0.30246 (7)	0.3692 (2)	0.0191 (3)
C8	0.34949 (13)	0.32942 (7)	0.3085 (2)	0.0193 (3)
H8A	0.3365	0.3790	0.3080	0.023*
C9	0.25383 (12)	0.28457 (7)	0.2485 (2)	0.0188 (3)
C10	0.13113 (13)	0.31369 (7)	0.1898 (2)	0.0205 (3)
C11	0.02459 (13)	0.28273 (8)	0.2451 (2)	0.0245 (3)
H11A	0.0301	0.2420	0.3193	0.029*
C12	−0.08913 (14)	0.31153 (9)	0.1918 (2)	0.0315 (4)
H12A	−0.1613	0.2909	0.2313	0.038*
C13	−0.09812 (16)	0.37035 (9)	0.0810 (3)	0.0366 (5)
H13A	−0.1763	0.3894	0.0432	0.044*
C14	0.00695 (16)	0.40117 (8)	0.0257 (3)	0.0336 (4)
H14A	0.0008	0.4413	−0.0506	0.040*
C15	0.12153 (14)	0.37363 (8)	0.0814 (2)	0.0253 (4)
H15A	0.1935	0.3957	0.0455	0.030*
C16	0.39525 (12)	0.18928 (7)	0.3197 (2)	0.0192 (3)
C17	0.27805 (12)	0.21180 (7)	0.2504 (2)	0.0196 (3)
C18	0.19270 (13)	0.16011 (7)	0.1769 (2)	0.0207 (3)
C19	0.53384 (14)	0.09527 (8)	0.3919 (2)	0.0253 (4)
H19A	0.5373	0.0437	0.3870	0.038*
H19B	0.5509	0.1109	0.5164	0.038*
H19C	0.5952	0.1152	0.3179	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0235 (5)	0.0159 (5)	0.0299 (7)	−0.0003 (4)	−0.0009 (5)	−0.0005 (4)
N1	0.0209 (7)	0.0207 (6)	0.0401 (9)	−0.0028 (5)	−0.0015 (6)	0.0034 (6)
N2	0.0220 (6)	0.0173 (6)	0.0195 (7)	−0.0007 (4)	0.0010 (5)	−0.0008 (5)
N3	0.0258 (7)	0.0226 (6)	0.0298 (8)	−0.0015 (5)	0.0006 (6)	−0.0012 (6)
C1	0.0190 (7)	0.0201 (7)	0.0172 (8)	−0.0004 (5)	0.0018 (6)	−0.0022 (6)
C2	0.0190 (7)	0.0212 (7)	0.0231 (8)	0.0017 (5)	0.0009 (6)	0.0008 (6)
C3	0.0223 (7)	0.0166 (6)	0.0277 (9)	0.0001 (5)	0.0020 (6)	0.0003 (6)
C4	0.0192 (7)	0.0213 (7)	0.0230 (8)	−0.0025 (5)	0.0033 (6)	−0.0010 (6)
C5	0.0197 (7)	0.0207 (7)	0.0285 (9)	0.0004 (5)	−0.0010 (6)	0.0004 (6)
C6	0.0226 (7)	0.0169 (6)	0.0260 (9)	0.0004 (5)	0.0023 (6)	0.0006 (6)
C7	0.0231 (7)	0.0183 (6)	0.0161 (8)	−0.0008 (5)	0.0029 (6)	−0.0010 (6)
C8	0.0225 (7)	0.0163 (6)	0.0190 (8)	0.0000 (5)	0.0017 (6)	−0.0013 (6)
C9	0.0208 (7)	0.0202 (7)	0.0155 (8)	−0.0011 (5)	0.0028 (5)	−0.0011 (6)
C10	0.0225 (7)	0.0214 (7)	0.0169 (8)	0.0010 (5)	−0.0021 (6)	−0.0056 (6)
C11	0.0241 (7)	0.0260 (7)	0.0233 (9)	−0.0008 (6)	0.0010 (6)	−0.0077 (7)
C12	0.0229 (8)	0.0363 (8)	0.0348 (10)	0.0010 (6)	−0.0002 (7)	−0.0150 (8)
C13	0.0314 (9)	0.0347 (9)	0.0414 (11)	0.0114 (7)	−0.0105 (8)	−0.0154 (8)
C14	0.0424 (9)	0.0238 (7)	0.0323 (10)	0.0099 (7)	−0.0101 (8)	−0.0056 (7)
C15	0.0316 (8)	0.0200 (7)	0.0235 (9)	0.0010 (6)	−0.0023 (7)	−0.0052 (6)
C16	0.0240 (7)	0.0163 (6)	0.0177 (8)	−0.0014 (5)	0.0041 (6)	0.0006 (6)
C17	0.0197 (7)	0.0212 (7)	0.0179 (8)	−0.0025 (5)	0.0015 (6)	−0.0011 (6)
C18	0.0224 (7)	0.0194 (6)	0.0201 (8)	0.0001 (5)	0.0016 (6)	0.0005 (6)
C19	0.0280 (8)	0.0199 (7)	0.0277 (9)	0.0030 (6)	0.0004 (6)	0.0026 (6)

Geometric parameters (Å, º) top

O1—C16	1.3498 (16)	C8—C9	1.3937 (18)
O1—C19	1.4427 (17)	C8—H8A	0.9500
N1—C4	1.3786 (18)	C9—C17	1.405 (2)
N1—H2N1	0.916 (19)	C9—C10	1.4844 (18)
N1—H1N1	0.91 (2)	C10—C15	1.395 (2)
N2—C16	1.3144 (17)	C10—C11	1.398 (2)
N2—C7	1.3589 (17)	C11—C12	1.387 (2)
N3—C18	1.1513 (18)	C11—H11A	0.9500
C1—C2	1.401 (2)	C12—C13	1.388 (3)
C1—C6	1.4032 (18)	C12—H12A	0.9500
C1—C7	1.4718 (18)	C13—C14	1.383 (3)
C2—C3	1.3815 (19)	C13—H13A	0.9500
C2—H2A	0.9500	C14—C15	1.390 (2)
C3—C4	1.4052 (19)	C14—H14A	0.9500
C3—H3A	0.9500	C15—H15A	0.9500
C4—C5	1.401 (2)	C16—C17	1.4094 (19)
C5—C6	1.3811 (19)	C17—C18	1.4317 (19)
C5—H5A	0.9500	C19—H19A	0.9800
C6—H6A	0.9500	C19—H19B	0.9800
C7—C8	1.3968 (19)	C19—H19C	0.9800

C16—O1—C19	116.38 (10)	C15—C10—C11	119.30 (13)
C4—N1—H2N1	116.6 (11)	C15—C10—C9	119.85 (13)
C4—N1—H1N1	117.2 (12)	C11—C10—C9	120.84 (14)
H2N1—N1—H1N1	116.0 (17)	C12—C11—C10	120.01 (15)
C16—N2—C7	118.28 (12)	C12—C11—H11A	120.0
C2—C1—C6	117.41 (12)	C10—C11—H11A	120.0
C2—C1—C7	122.29 (12)	C11—C12—C13	120.37 (16)
C6—C1—C7	120.29 (12)	C11—C12—H12A	119.8
C3—C2—C1	121.80 (13)	C13—C12—H12A	119.8
C3—C2—H2A	119.1	C14—C13—C12	119.87 (15)
C1—C2—H2A	119.1	C14—C13—H13A	120.1
C2—C3—C4	120.24 (13)	C12—C13—H13A	120.1
C2—C3—H3A	119.9	C13—C14—C15	120.24 (16)
C4—C3—H3A	119.9	C13—C14—H14A	119.9
N1—C4—C5	120.41 (13)	C15—C14—H14A	119.9
N1—C4—C3	121.11 (13)	C14—C15—C10	120.19 (16)
C5—C4—C3	118.45 (12)	C14—C15—H15A	119.9
C6—C5—C4	120.69 (13)	C10—C15—H15A	119.9
C6—C5—H5A	119.7	N2—C16—O1	119.59 (12)
C4—C5—H5A	119.7	N2—C16—C17	124.49 (13)
C5—C6—C1	121.41 (13)	O1—C16—C17	115.92 (12)
C5—C6—H6A	119.3	C9—C17—C16	117.80 (12)
C1—C6—H6A	119.3	C9—C17—C18	123.51 (12)
N2—C7—C8	121.10 (12)	C16—C17—C18	118.60 (13)
N2—C7—C1	115.91 (12)	N3—C18—C17	177.54 (15)
C8—C7—C1	122.99 (12)	O1—C19—H19A	109.5
C9—C8—C7	120.85 (12)	O1—C19—H19B	109.5
C9—C8—H8A	119.6	H19A—C19—H19B	109.5
C7—C8—H8A	119.6	O1—C19—H19C	109.5
C8—C9—C17	117.39 (12)	H19A—C19—H19C	109.5
C8—C9—C10	120.36 (12)	H19B—C19—H19C	109.5
C17—C9—C10	122.24 (12)

C6—C1—C2—C3	0.6 (2)	C8—C9—C10—C11	−135.09 (16)
C7—C1—C2—C3	−178.29 (15)	C17—C9—C10—C11	43.4 (2)
C1—C2—C3—C4	−0.5 (2)	C15—C10—C11—C12	0.2 (2)
C2—C3—C4—N1	−178.14 (15)	C9—C10—C11—C12	178.71 (14)
C2—C3—C4—C5	−0.2 (2)	C10—C11—C12—C13	1.1 (2)
N1—C4—C5—C6	178.73 (16)	C11—C12—C13—C14	−1.0 (3)
C3—C4—C5—C6	0.7 (2)	C12—C13—C14—C15	−0.3 (3)
C4—C5—C6—C1	−0.7 (2)	C13—C14—C15—C10	1.6 (3)
C2—C1—C6—C5	0.0 (2)	C11—C10—C15—C14	−1.5 (2)
C7—C1—C6—C5	178.90 (15)	C9—C10—C15—C14	179.94 (14)
C16—N2—C7—C8	2.8 (2)	C7—N2—C16—O1	179.46 (13)
C16—N2—C7—C1	−177.88 (13)	C7—N2—C16—C17	−0.5 (2)
C2—C1—C7—N2	169.00 (15)	C19—O1—C16—N2	−1.2 (2)
C6—C1—C7—N2	−9.9 (2)	C19—O1—C16—C17	178.69 (14)
C2—C1—C7—C8	−11.7 (2)	C8—C9—C17—C16	2.7 (2)
C6—C1—C7—C8	169.48 (15)	C10—C9—C17—C16	−175.87 (14)
N2—C7—C8—C9	−2.3 (2)	C8—C9—C17—C18	−173.75 (14)
C1—C7—C8—C9	178.41 (14)	C10—C9—C17—C18	7.7 (2)
C7—C8—C9—C17	−0.5 (2)	N2—C16—C17—C9	−2.3 (2)
C7—C8—C9—C10	178.05 (14)	O1—C16—C17—C9	177.76 (14)
C8—C9—C10—C15	43.4 (2)	N2—C16—C17—C18	174.30 (15)
C17—C9—C10—C15	−138.05 (15)	O1—C16—C17—C18	−5.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N1···N3ⁱ	0.915 (19)	2.338 (19)	3.2416 (18)	169.5 (19)
N1—H1N1···N3ⁱⁱ	0.91 (2)	2.28 (2)	3.1773 (19)	168 (2)
C11—H11A···Cg3ⁱⁱⁱ	0.95	2.87	3.7667 (17)	158
C19—H19C···Cg2^iv	0.98	2.69	3.5156 (17)	142

Symmetry codes: (i) x+1, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y−1/2, z−1/2; (iv) x, −y−1/2, z−3/2.

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N1···N3ⁱ	0.915 (19)	2.338 (19)	3.2416 (18)	169.5 (19)
N1—H1N1···N3ⁱⁱ	0.91 (2)	2.28 (2)	3.1773 (19)	168 (2)
C11—H11A···Cg3ⁱⁱⁱ	0.95	2.87	3.7667 (17)	158
C19—H19C···Cg2^iv	0.98	2.69	3.5156 (17)	142

Symmetry codes: (i) x+1, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y−1/2, z−1/2; (iv) x, −y−1/2, z−3/2.

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 extend their appreciation to the Prince of Songkla University and the Universiti Sains Malaysia for the APEX DE2012 grant No. 1002/PFIZIK/910323.

References

Al-Jaber, N. A., Bougasim, A. S. A. & Karah, M. M. S. (2012). J. Saudi Chem. Soc. 16, 45–53. CAS Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Brandt, W., Mologni, L., Preu, L., Lemcke, T., Gambacorti-Passerini, C. & Kunick, C. (2010). Eur. J. Med. Chem. 45, 2919–2927. Web of Science CrossRef CAS PubMed Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chantrapromma, S., Suwunwong, T., Ruanwas, P., Quah, C. K. & Fun, H.-K. (2013). Acta Cryst. E69, o1500–o1501. CSD CrossRef CAS IUCr Journals Google Scholar
El-Sayed, H. A., Moustafa, A. H., Haikal, A. E.-F. Z., Abu-El-Halawa, R. & Ashry, E. S. H. E. (2011). Eur. J. Med. Chem. 46, 2948–2954. Web of Science CAS PubMed Google Scholar
Ji, J., Bunnelle, W. H., Anderson, D. J., Faltynek, C., Dyhring, T., Ahring, P. K., Rueter, L. E., Curzon, P., Buckley, M. J., Marsh, K. C., Kempf-Grote, A. & Meyer, M. D. (2007). Biochem. Pharmacol. 74, 1253–1262. Web of Science CrossRef PubMed CAS Google Scholar
Kim, K.-R., Rhee, S.-D., Kim, H. Y., Jung, W. H., Yang, S.-D., Kim, S. S., Ahn, J. H. & Cheon, H. G. (2005). Eur. J. Pharmacol. 518, 63–70. Web of Science CrossRef PubMed CAS Google Scholar
Koner, R. R., Sinha, S., Kumar, S., Nandi, C. K. & Ghosh, S. (2012). Tetrahedron Lett. 53, 2302–2307. Web of Science CrossRef CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Raghukumar, V., Thirumalai, D., Ramakrishnan, V. T., Karunakara, V. & Ramamurthy, P. (2003). Tetrahedron, 59, 3761–3768. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2012). Acta Cryst. E68, o2812–o2813. CSD CrossRef CAS IUCr Journals Google Scholar
Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2013). J. Chem. Crystallogr. 43, 538–543. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhou, W.-J., Ji, S.-J. & Shen, Z.-L. (2006). J. Organomet. Chem. 691, 1356–1360. Web of Science CrossRef CAS Google Scholar

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Volume 69| Part 12| December 2013| Pages o1816-o1817

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