2-(2-Hy­droxy-3-meth­oxy­phen­yl)-6H-perimidin-6-one

Fun, H.-K.; Chanawanno, K.; Chantrapromma, S.

doi:10.1107/S1600536811006465

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages o715-o716

doi:10.1107/S1600536811006465

Open

access

2-(2-Hydroxy-3-methoxyphenyl)-6H-perimidin-6-one

Hoong-Kun Fun,^a ^*‡ Kullapa Chanawanno ^b and Suchada Chantrapromma ^b §

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 14 February 2011; accepted 20 February 2011; online 26 February 2011)

The molecule of the title perimidine derivative, C₁₈H₁₂N₂O₃, is essentially planar, the dihedral angle between the benzene and perimidine rings being 3.25 (5)°. The hydroxy and methoxy groups lie in the plane of the benzene ring to which they are bound [O—C—C—C = 179.96 (11)° and C—O—C—C = −177.96 (12)°]. An intramolecular O—H⋯N interaction generates an S(6) ring motif. In the crystal, molecules are linked by pairs of C—H⋯O interactions into dimers, which generate S(16) ring motifs. These dimers are arranged into sheets parallel to the ac plane and further stacked down the b axis by π–π interactions, with centroid–centroid distances in the range 3.5066 (8)–3.7241 (7) Å.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For background to perimidines and their applications, see: Claramunt et al. (1995 ); del Valle et al. (1997 ); Herbert et al. (1987 ); Llamas-Saiz et al. (1995 ); Pozharskii & Dalnikovskaya (1981 ); Varsha et al. (2010 ). For related structures, see: Llamas-Saiz et al. (1995); Varsha et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₈H₁₂N₂O₃
M_r = 304.30
Monoclinic, C 2/c
a = 25.4718 (17) Å
b = 7.0666 (3) Å
c = 15.0815 (6) Å
β = 94.373 (3)°
V = 2706.8 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.67 × 0.11 × 0.05 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.933, T_max = 0.994
42939 measured reflections
6529 independent reflections
3471 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.210
S = 1.02
6529 reflections
255 parameters
All H-atom parameters refined
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N2	0.91 (2)	1.73 (2)	2.5583 (15)	151 (2)
C15—H15⋯O2ⁱ	0.970 (18)	2.437 (18)	3.3686 (17)	160.8 (12)
Symmetry code: (i) $[-x+2, y, -z+{\script{3\over 2}}]$ .

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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006465/sj5107sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006465/sj5107Isup2.hkl

checkCIF report

Comment top

Perimidines (peri-naphtho-fused perimidine ring systems) have received wide interests due to their applications in photophysics (del Valle et al., 1997), usage as coloring materials for polyester fibers (Claramunt et al., 1995) and fluorescent materials (Varsha et al., 2010). They are also noted for their biological activity displaying antiulcer, antifungal, antimicrobial and antitumor properties (Claramunt et al., 1995; Herbert et al., 1987; Pozharskii & Dalnikovskaya, 1981). In an attempt to synthesize a Co(II) Schiff base complex by the reaction of o-vanillin, 1,8-diaminonaphthalene and CoCl₂.6H₂O, the unexpected product was the perimidine derivative, (I), reported here, Fig 1.

In the molecule of the title perimidine derivative (I), C₁₈H₁₂N₂O₃, the perimidine ring system (N1–N2/C7–C17) is planar with an r.m.s deviation 0.0126 (11)Å. The whole molecule is essentially planar with the dihedral angle between the perimidine and phenyl rings being 3.25 (5)°. Both the hydroxy and methoxy groups are co-planar with the attached benzene ring with torsion angles O2–C2–C3–C4 = 179.96 (11)° and C18–O3–C3–C2 = -177.96 (12)°. An intramolecular O—H···N interaction generates an S(6) ring motif (Bernstein et al., 1995) and helps to stabilize the planarity of the molecule (Fig. 1). Bond distances are normal (Allen et al., 1987) and are comparable to those found in related structures (Llamas-Saiz et al., 1995; Varsha et al., 2010).

In the crystal structure (Fig. 2), the molecules are linked by two C—H···O interactions (Table 1) into dimers which generate S(16) ring motifs. These dimers are arranged into sheets parallel to the ac plane and further stacked down the b axis by π–π interactions with centroid to centroid distances Cg₁···Cg₂ ⁱⁱ= 3.7241 (7) Å; Cg₂···Cg₃ ⁱⁱ= 3.5066 (8) Å; Cg₂···Cg₄ ⁱⁱ= 3.7055 (8) Å and Cg₂···Cg₄ ⁱⁱⁱ= 3.5988 (8) Å (symmetry codes (ii) = 2 - x, 1 - y, 1 - z and (iii) = 2 - x, 2 - y, 2 - z). Cg1, Cg2, Cg3, and Cg4 are the centroids of the N1–N2/C7–C8/C6–C17, C1–C6, C8–C12/C17, and C12–C17 rings, respectively.

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For background to perimidines and their applications, see: Claramunt et al. (1995); del Valle et al. (1997); Herbert et al. (1987); Llamas-Saiz et al. (1995); Pozharskii & Dalnikovskaya (1981); Varsha et al. (2010). For related structures, see: Llamas-Saiz et al. (1995); Varsha et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was synthesized by adding a solution of 1,8-diaminonaphthalene (0.50 g, 3.16 mmol) in ethanol (20 ml) dropwise to a solution of o-vanillin (0.96 g, 6.32 mmol) in ethanol (10 ml). The reaction mixture was stirred for 0.5 h at room temperature and a pale-orange precipitate was obtained. After filtration, the pale-orange solid was washed with diethyl ether. A solution of the pale-orange solid (0.20 g, 0.47 mmol) in ethanol (20 ml) was slowly added to a solution of CoCl₂.6H₂O (0.11 g, 0.47 mmol) in 10 ml of ethanol followed by triethylamine (0.06 ml, 0.47 mmol). The mixture was refluxed for 3 h. The title compound was obtained as a purple solid and washed with diethyl ether. The purple needle-shaped single crystals of the unexpected perimidine derivative of the title compound suitable for x-ray structure determination were recrystallized from ethanol by slow evaporation of the solvent at room temperature over several days, Mp. 507–508 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 and the atom-numbering scheme. An intramolecular hydrogen bond is drawn as a dashed line.
	Fig. 2. The crystal packing of the title compound viewed down the b axis. Hydrogen bonds were drawn as dashed lines.

2-(2-Hydroxy-3-methoxyphenyl)-6H-perimidin-6-one top

Crystal data top

C₁₈H₁₂N₂O₃	F(000) = 1264
M_r = 304.30	D_x = 1.493 Mg m⁻³
Monoclinic, C2/c	Melting point = 507–508 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 25.4718 (17) Å	Cell parameters from 6529 reflections
b = 7.0666 (3) Å	θ = 1.6–36.3°
c = 15.0815 (6) Å	µ = 0.10 mm⁻¹
β = 94.373 (3)°	T = 100 K
V = 2706.8 (2) Å³	Needle, purple
Z = 8	0.67 × 0.11 × 0.05 mm

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	6529 independent reflections
Radiation source: sealed tube	3471 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ϕ and ω scans	θ_max = 36.3°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −42→34
T_min = 0.933, T_max = 0.994	k = −11→11
42939 measured reflections	l = −24→25

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.210	All H-atom parameters refined
S = 1.02	w = 1/[σ²(F_o²) + (0.110P)²] where P = (F_o² + 2F_c²)/3
6529 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₈H₁₂N₂O₃	V = 2706.8 (2) Å³
M_r = 304.30	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.4718 (17) Å	µ = 0.10 mm⁻¹
b = 7.0666 (3) Å	T = 100 K
c = 15.0815 (6) Å	0.67 × 0.11 × 0.05 mm
β = 94.373 (3)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	6529 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3471 reflections with I > 2σ(I)
T_min = 0.933, T_max = 0.994	R_int = 0.072
42939 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.210	All H-atom parameters refined
S = 1.02	Δρ_max = 0.57 e Å⁻³
6529 reflections	Δρ_min = −0.29 e Å⁻³
255 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	1.20986 (4)	0.86652 (17)	0.36853 (7)	0.0390 (3)
O2	0.93604 (4)	0.76137 (15)	0.66009 (7)	0.0305 (2)
H1O2	0.9692 (9)	0.784 (3)	0.6441 (15)	0.068 (7)*
O3	0.83728 (4)	0.69274 (15)	0.67439 (7)	0.0307 (2)
N1	1.00314 (4)	0.71962 (15)	0.40931 (7)	0.0230 (2)
N2	1.01534 (4)	0.77988 (14)	0.56606 (7)	0.0217 (2)
C1	0.92971 (5)	0.68964 (16)	0.50224 (9)	0.0213 (2)
C2	0.90819 (5)	0.70778 (17)	0.58472 (9)	0.0229 (3)
C3	0.85404 (5)	0.66982 (18)	0.59105 (9)	0.0245 (3)
C4	0.82297 (5)	0.61425 (18)	0.51641 (10)	0.0269 (3)
H4	0.7846 (8)	0.588 (3)	0.5190 (13)	0.053 (5)*
C5	0.84470 (5)	0.59241 (19)	0.43503 (9)	0.0271 (3)
H5	0.8242 (6)	0.542 (2)	0.3839 (11)	0.032 (4)*
C6	0.89730 (5)	0.62922 (18)	0.42762 (9)	0.0242 (3)
H6	0.9121 (6)	0.608 (3)	0.3716 (12)	0.039 (5)*
C7	0.98576 (5)	0.73220 (16)	0.49261 (9)	0.0208 (2)
C8	1.05351 (5)	0.75829 (17)	0.40160 (9)	0.0222 (2)
C9	1.07449 (5)	0.7429 (2)	0.31468 (9)	0.0271 (3)
H9	1.0495 (6)	0.696 (2)	0.2625 (11)	0.027 (4)*
C10	1.12551 (5)	0.7780 (2)	0.30472 (9)	0.0281 (3)
H10	1.1420 (6)	0.761 (2)	0.2446 (11)	0.031 (4)*
C11	1.16293 (5)	0.83502 (19)	0.37912 (9)	0.0269 (3)
C12	1.14203 (5)	0.84961 (17)	0.46741 (9)	0.0233 (3)
C13	1.17405 (5)	0.89476 (19)	0.54295 (9)	0.0268 (3)
H13	1.2155 (6)	0.916 (2)	0.5341 (11)	0.032*
C14	1.15283 (5)	0.90293 (19)	0.62651 (10)	0.0284 (3)
H14	1.1753 (6)	0.931 (2)	0.6784 (10)	0.029 (4)*
C15	1.10056 (5)	0.86583 (18)	0.63559 (9)	0.0257 (3)
H15	1.0859 (6)	0.865 (2)	0.6931 (12)	0.036 (4)*
C16	1.06736 (5)	0.81935 (16)	0.55893 (9)	0.0218 (2)
C17	1.08818 (5)	0.81121 (16)	0.47560 (8)	0.0206 (2)
C18	0.78320 (6)	0.6497 (2)	0.68447 (12)	0.0338 (3)
H18A	0.7621 (7)	0.737 (3)	0.6464 (12)	0.039 (5)*
H18B	0.7746 (6)	0.521 (3)	0.6683 (10)	0.032 (4)*
H18C	0.7805 (7)	0.666 (2)	0.7467 (12)	0.035 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0255 (5)	0.0525 (7)	0.0408 (6)	−0.0050 (5)	0.0157 (4)	0.0022 (5)
O2	0.0225 (5)	0.0393 (6)	0.0313 (5)	−0.0060 (4)	0.0121 (4)	−0.0095 (4)
O3	0.0201 (4)	0.0387 (6)	0.0353 (5)	−0.0036 (4)	0.0158 (4)	−0.0050 (4)
N1	0.0213 (5)	0.0227 (5)	0.0261 (6)	0.0006 (4)	0.0090 (4)	0.0043 (4)
N2	0.0189 (5)	0.0195 (5)	0.0278 (6)	−0.0018 (4)	0.0099 (4)	−0.0012 (4)
C1	0.0201 (5)	0.0168 (5)	0.0282 (6)	0.0001 (4)	0.0088 (5)	0.0031 (4)
C2	0.0204 (6)	0.0202 (5)	0.0290 (7)	−0.0007 (4)	0.0089 (5)	−0.0003 (4)
C3	0.0222 (6)	0.0220 (5)	0.0309 (7)	0.0002 (4)	0.0112 (5)	0.0011 (5)
C4	0.0186 (6)	0.0244 (6)	0.0383 (8)	−0.0017 (5)	0.0073 (5)	0.0059 (5)
C5	0.0235 (6)	0.0268 (6)	0.0313 (7)	−0.0019 (5)	0.0036 (5)	0.0066 (5)
C6	0.0245 (6)	0.0234 (6)	0.0254 (6)	−0.0002 (4)	0.0066 (5)	0.0054 (5)
C7	0.0213 (5)	0.0171 (5)	0.0253 (6)	0.0013 (4)	0.0092 (5)	0.0019 (4)
C8	0.0212 (5)	0.0196 (5)	0.0266 (6)	0.0013 (4)	0.0079 (5)	0.0041 (4)
C9	0.0265 (6)	0.0316 (6)	0.0244 (6)	0.0006 (5)	0.0096 (5)	0.0042 (5)
C10	0.0273 (6)	0.0330 (7)	0.0254 (7)	0.0006 (5)	0.0118 (5)	0.0051 (5)
C11	0.0249 (6)	0.0271 (6)	0.0304 (7)	0.0000 (5)	0.0127 (5)	0.0043 (5)
C12	0.0204 (5)	0.0213 (5)	0.0297 (6)	−0.0008 (4)	0.0109 (5)	0.0026 (5)
C13	0.0219 (6)	0.0261 (6)	0.0336 (7)	−0.0046 (5)	0.0090 (5)	0.0000 (5)
C14	0.0248 (6)	0.0295 (6)	0.0319 (7)	−0.0057 (5)	0.0077 (5)	−0.0041 (5)
C15	0.0245 (6)	0.0263 (6)	0.0273 (7)	−0.0051 (5)	0.0100 (5)	−0.0033 (5)
C16	0.0211 (5)	0.0175 (5)	0.0281 (6)	−0.0020 (4)	0.0104 (4)	−0.0016 (4)
C17	0.0210 (5)	0.0168 (5)	0.0253 (6)	0.0000 (4)	0.0094 (4)	0.0024 (4)
C18	0.0192 (6)	0.0437 (9)	0.0405 (9)	−0.0047 (6)	0.0145 (6)	−0.0017 (7)

Geometric parameters (Å, º) top

O1—C11	1.2384 (16)	C8—C17	1.4196 (18)
O2—C2	1.3474 (16)	C8—C9	1.4568 (19)
O2—H1O2	0.91 (2)	C9—C10	1.3427 (19)
O3—C3	1.3676 (16)	C9—H9	1.028 (16)
O3—C18	1.4301 (16)	C10—C11	1.472 (2)
N1—C8	1.3256 (16)	C10—H10	1.035 (17)
N1—C7	1.3663 (17)	C11—C12	1.4747 (18)
N2—C7	1.3345 (17)	C12—C13	1.3868 (19)
N2—C16	1.3664 (16)	C12—C17	1.4127 (17)
C1—C2	1.4030 (18)	C13—C14	1.4098 (19)
C1—C6	1.4102 (19)	C13—H13	1.085 (16)
C1—C7	1.4769 (17)	C14—C15	1.3739 (18)
C2—C3	1.4155 (17)	C14—H14	0.955 (15)
C3—C4	1.3827 (19)	C15—C16	1.4179 (18)
C4—C5	1.393 (2)	C15—H15	0.970 (17)
C4—H4	1.000 (19)	C16—C17	1.4019 (18)
C5—C6	1.3777 (18)	C18—H18A	0.976 (18)
C5—H5	0.966 (16)	C18—H18B	0.963 (17)
C6—H6	0.963 (18)	C18—H18C	0.954 (18)

C2—O2—H1O2	105.4 (14)	C9—C10—C11	122.77 (12)
C3—O3—C18	116.32 (11)	C9—C10—H10	122.6 (9)
C8—N1—C7	116.80 (11)	C11—C10—H10	114.6 (9)
C7—N2—C16	118.40 (11)	O1—C11—C10	121.75 (12)
C2—C1—C6	119.38 (11)	O1—C11—C12	121.49 (13)
C2—C1—C7	120.97 (11)	C10—C11—C12	116.75 (11)
C6—C1—C7	119.65 (11)	C13—C12—C17	119.11 (12)
O2—C2—C1	123.88 (11)	C13—C12—C11	121.84 (12)
O2—C2—C3	116.70 (11)	C17—C12—C11	119.03 (12)
C1—C2—C3	119.41 (12)	C12—C13—C14	120.14 (12)
O3—C3—C4	125.62 (12)	C12—C13—H13	116.6 (8)
O3—C3—C2	114.43 (12)	C14—C13—H13	123.2 (8)
C4—C3—C2	119.95 (12)	C15—C14—C13	121.45 (13)
C3—C4—C5	120.50 (12)	C15—C14—H14	118.9 (9)
C3—C4—H4	121.5 (11)	C13—C14—H14	119.6 (9)
C5—C4—H4	118.0 (11)	C14—C15—C16	119.02 (12)
C6—C5—C4	120.32 (13)	C14—C15—H15	122.2 (10)
C6—C5—H5	118.3 (9)	C16—C15—H15	118.7 (10)
C4—C5—H5	121.2 (9)	N2—C16—C17	119.84 (11)
C5—C6—C1	120.42 (12)	N2—C16—C15	120.32 (11)
C5—C6—H6	119.3 (10)	C17—C16—C15	119.84 (11)
C1—C6—H6	120.2 (10)	C16—C17—C12	120.44 (12)
N2—C7—N1	125.29 (11)	C16—C17—C8	117.41 (11)
N2—C7—C1	117.29 (11)	C12—C17—C8	122.12 (11)
N1—C7—C1	117.42 (11)	O3—C18—H18A	107.1 (10)
N1—C8—C17	122.25 (12)	O3—C18—H18B	112.2 (9)
N1—C8—C9	119.17 (12)	H18A—C18—H18B	110.1 (14)
C17—C8—C9	118.57 (11)	O3—C18—H18C	102.7 (10)
C10—C9—C8	120.76 (13)	H18A—C18—H18C	115.0 (15)
C10—C9—H9	121.4 (9)	H18B—C18—H18C	109.5 (14)
C8—C9—H9	117.7 (9)

C6—C1—C2—O2	178.87 (11)	C8—C9—C10—C11	−0.6 (2)
C7—C1—C2—O2	−0.90 (19)	C9—C10—C11—O1	179.92 (13)
C6—C1—C2—C3	−1.62 (18)	C9—C10—C11—C12	1.0 (2)
C7—C1—C2—C3	178.60 (10)	O1—C11—C12—C13	−1.6 (2)
C18—O3—C3—C4	1.88 (19)	C10—C11—C12—C13	177.40 (12)
C18—O3—C3—C2	−177.96 (12)	O1—C11—C12—C17	−179.71 (12)
O2—C2—C3—O3	−0.19 (17)	C10—C11—C12—C17	−0.76 (17)
C1—C2—C3—O3	−179.73 (10)	C17—C12—C13—C14	−0.32 (19)
O2—C2—C3—C4	179.96 (11)	C11—C12—C13—C14	−178.48 (12)
C1—C2—C3—C4	0.42 (18)	C12—C13—C14—C15	0.4 (2)
O3—C3—C4—C5	−178.86 (12)	C13—C14—C15—C16	−0.3 (2)
C2—C3—C4—C5	0.98 (19)	C7—N2—C16—C17	0.73 (17)
C3—C4—C5—C6	−1.1 (2)	C7—N2—C16—C15	−178.36 (11)
C4—C5—C6—C1	−0.1 (2)	C14—C15—C16—N2	179.33 (12)
C2—C1—C6—C5	1.47 (18)	C14—C15—C16—C17	0.24 (19)
C7—C1—C6—C5	−178.75 (11)	N2—C16—C17—C12	−179.29 (10)
C16—N2—C7—N1	−0.21 (18)	C15—C16—C17—C12	−0.20 (18)
C16—N2—C7—C1	179.80 (10)	N2—C16—C17—C8	−0.99 (17)
C8—N1—C7—N2	−0.03 (18)	C15—C16—C17—C8	178.10 (11)
C8—N1—C7—C1	179.96 (10)	C13—C12—C17—C16	0.24 (18)
C2—C1—C7—N2	2.97 (17)	C11—C12—C17—C16	178.45 (10)
C6—C1—C7—N2	−176.80 (11)	C13—C12—C17—C8	−177.98 (11)
C2—C1—C7—N1	−177.02 (10)	C11—C12—C17—C8	0.23 (18)
C6—C1—C7—N1	3.21 (16)	N1—C8—C17—C16	0.77 (17)
C7—N1—C8—C17	−0.26 (17)	C9—C8—C17—C16	−178.10 (11)
C7—N1—C8—C9	178.60 (11)	N1—C8—C17—C12	179.04 (11)
N1—C8—C9—C10	−178.90 (12)	C9—C8—C17—C12	0.17 (17)
C17—C8—C9—C10	0.01 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N2	0.91 (2)	1.73 (2)	2.5583 (15)	151 (2)
C15—H15···O2ⁱ	0.970 (18)	2.437 (18)	3.3686 (17)	160.8 (12)

Symmetry code: (i) −x+2, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂N₂O₃
M_r	304.30
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	25.4718 (17), 7.0666 (3), 15.0815 (6)
β (°)	94.373 (3)
V (Å³)	2706.8 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.67 × 0.11 × 0.05

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.933, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	42939, 6529, 3471
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.833

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.210, 1.02
No. of reflections	6529
No. of parameters	255
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.29

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N2	0.91 (2)	1.73 (2)	2.5583 (15)	151 (2)
C15—H15···O2ⁱ	0.970 (18)	2.437 (18)	3.3686 (17)	160.8 (12)

Symmetry code: (i) −x+2, y, −z+3/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

KC thanks the Crystal Materials Research Unit (CMRU), Prince of Songkla University, for a research assistance fellowship. Generous support by the Prince of Songkla University is gratefully acknowledged. The authors also thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

References

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
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Claramunt, R. M., Dotor, J. & Elguero, J. (1995). Ann. Quim. 91, 151–183. CAS Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Herbert, J. M., Woodgate, P. D. & Denny, W. A. (1987). J. Med. Chem. 30, 2081–2086. CrossRef CAS PubMed Web of Science Google Scholar
Llamas-Saiz, A. L., Foces-Foces, C., Sanz, D., Claramunt, R. M., Dotor, J., Elguero, J., Catalán, J. & del Valle, J. C. (1995). J. Chem. Soc. Perkin Trans. 2, pp. 1389–1398. Google Scholar
Pozharskii, A. F. & Dalnikovskaya, V. V. (1981). Russ. Chem. Rev. 50, 816–835. CrossRef 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
Valle, J. C. del, Catalán, J., Faces-Foces, C., Llamas-Saiz, A. L., Elguero, J., Sanz, D., Dotor, J. & Claramunt, R. M. (1997). J. Lumin. 75, 17–26. Google Scholar
Varsha, G., Arun, V., Robinson, P. P., Sebastian, M., Varghese, D., Leeju, P., Jayachandran, V. P. & Yusuff, K. K. M. (2010). Tetrahedron Lett.. 51, 2174–2177. Web of Science CSD CrossRef CAS Google Scholar