1-[(E)-(3,4-Dimethyl­isoxazol-5-yl)imino­meth­yl]-2-naphthol

Fun, H.-K.; Hemamalini, M.; Asiri, A.M.; Khan, S.A.

doi:10.1107/S160053681001216X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages o1037-o1038

https://doi.org/10.1107/S160053681001216X

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1-[(E)-(3,4-Dimethylisoxazol-5-yl)iminomethyl]-2-naphthol

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a Abdullah M. Asiri ^b § and Salman A. Khan ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Faculty of Science, King Abdu Aziz University, Jeddah, Saudi Arabia
^*Correspondence e-mail: hkfun@usm.my

(Received 24 March 2010; accepted 31 March 2010; online 10 April 2010)

The title Schiff base compound, C₁₆H₁₄N₂O₂, has been synthesized by the reaction of 5-amino-3,4-dimethylisoxazole and 2-hydroxy-1-naphthaldehyde. The dihedral angle between the isoxazole ring and the napthyl ring system is 3.29 (7)°. The molecule adopts an E configuration about the central C=N double bond. Intramolecular O—H⋯N hydrogen bonding generates an S(6) ring motif. In the crystal structure, π–π interactions are observed involving the isoxazole ring and the substituted benzene ring of the naphthyl unit, with centroid–centroid distances of 3.5200 (10) Å.

Related literature

For related background and the biological activity of isoxazol, see: Howell & Kimmel (2008 ); Bartlett & Schleyerbach (1985 ); Lamani et al. (2009 ); Jayashankar et al. (2009 ). For related structures, see: Alvarez-Thon et al. (2006 ); Tahir et al. (2008 ); Shad et al. (2008 ); Fun et al. (2010 ). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₁₄N₂O₂
M_r = 266.29
Monoclinic, P 2₁ /c
a = 7.5250 (6) Å
b = 15.4643 (12) Å
c = 12.3982 (7) Å
β = 117.377 (4)°
V = 1281.17 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.79 × 0.06 × 0.05 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.930, T_max = 0.996
16577 measured reflections
3704 independent reflections
2843 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.134
S = 1.05
3704 reflections
237 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1	0.97 (2)	1.66 (3)	2.5471 (15)	150 (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: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681001216X/sj2761sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001216X/sj2761Isup2.hkl

checkCIF report

Comment top

Five-membered heterocyclic compounds, natural as well as synthetic, are important for their biological activities. Compounds with isoxazol rings are of interest due to their broad spectrum of biological activities against monoamine oxidase inhibitor (Howell & Kimmel, 2008), bacterial (Bartlett & Schleyerbach, 1985), depression (Lamani et al., 2009), hypertensive (Howell & Kimmel, 2008), pyretic and inflammatory diseases (Jayashankar et al., 2009). The crystal structures of 2-[(E)-(3,5-dimethylisoxazol- 4-yl)diazenyl]benzoic acid (Alvarez-Thon et al., 2006), 4-Bromo-2-((E)-{4-[(3,4-dimethylisoxazol-5-yl)sulfamoyl]phenyl}iminiomethyl)phenolate (Tahir et al., 2008), 4-Chloro-2-[(E)-({4-[N-(3,4-dimethyl isoxazol-5-yl)sulfamoyl]phenyl}iminio)methyl]phenolate (Shad et al., 2008) and 2-[(E)-(3,4-Dimethylisoxazol-5-yl) iminomethyl]phenol (Fun et al., 2010) have been reported previously. In view of the importance of the title compound, (I), its crystal structure is reported here.

In the title compound (Fig. 1), the isoxazole ring is essentially planar with a maximum deviation of 0.007 (2) Å for atom C13. The dihedral angle between the isoxazole (O2/N2/C12–C14) ring and the (C1–C4/C9–C10) ring of the naphthyl unit, is 3.29 (7)°. The C12—O2 and C11═N1 bond lengths are 1.3635 (14) Å and 1.3036 (15) Å, respectively, and agree with the corresponding values in 2-[(E)-(3,4-dimethylisoxazol-5-yl)iminomethyl]phenol [1.344 (3) and 1.292 (4) Å; Fun et al., 2010].

In the crystal structure (Fig. 2), the imino N atoms are linked to the phenol O atoms and act as hydrogen-bond acceptors in intramolecular O1—H1O1···N1 interactions (Table 1) , which generate S(6) ring motifs (Bernstein et al., 1995). The crystal structure is further stabilized by π–π interactions involving the isoxazole (O2/N2/C12–C14)ring and the (C1–C4/C9–C10) ring of the naphthyl unit, with centroid to centroid distance of 3.5200 (10) Å [symmetry code: -x, 2-y, 1-z].

Related literature top

For related background and the biological activity of isoxazol, see: Howell & Kimmel (2008); Bartlett & Schleyerbach (1985); Lamani et al. (2009); Jayashankar et al. (2009). For related structures, see: Alvarez-Thon et al. (2006); Tahir et al. (2008); Shad et al. (2008); Fun et al. (2010). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 5-amino-3,4-dimethylisoxazole (0.50 g, 0.0025 mol) and 2-hydroxy-1-naphthaledhyde (0.43 g, 0.0025 mol) in methanol (15 mL) was refluxed for 5 h with stirring to give a light yellow precipitate. Then it was filtered and washed with methanol to give the pure compound. Yield: 72%; m. p. 160° C. The sample was recrystalized from methanol by dissolving the crude product and leaving the solution to evaporate slowly at room temperature. IR (KBr) v(max) cm^-1: 2933 (C—H aromatic), 1626 (C═C), 1585 (HC═N), 1123 (C—N). ¹H NMR (600 MHz, CDCl₃) d: 8.30 (H3, d, J=12.72 Hz), 7.99 (H4, d, J=13.5 Hz), 7.87 (H5, d, J=11.76 Hz), 7.70 (H6, dd, J=8.58 Hz, J=5.1 Hz), 7.49 (H7, dd, J=10.8 Hz, J= 5.4 Hz), 7.34 (H9, s), 2.36 (-CH3, s), 2.15 (-CH3, s).

Structure description top

For related background and the biological activity of isoxazol, see: Howell & Kimmel (2008); Bartlett & Schleyerbach (1985); Lamani et al. (2009); Jayashankar et al. (2009). For related structures, see: Alvarez-Thon et al. (2006); Tahir et al. (2008); Shad et al. (2008); Fun et al. (2010). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, showing the hydrogen-bonded network (dashed lines). H atoms are not involved in hydrogen bond interactions are omitted for clarity.

1-[(E)-(3,4-Dimethylisoxazol-5-yl)iminomethyl]-2-naphthol top

Crystal data top

C₁₆H₁₄N₂O₂	F(000) = 560
M_r = 266.29	D_x = 1.381 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3616 reflections
a = 7.5250 (6) Å	θ = 2.6–34.2°
b = 15.4643 (12) Å	µ = 0.09 mm⁻¹
c = 12.3982 (7) Å	T = 100 K
β = 117.377 (4)°	Needle, yellow
V = 1281.17 (16) Å³	0.79 × 0.06 × 0.05 mm
Z = 4

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	3704 independent reflections
Radiation source: fine-focus sealed tube	2843 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 30.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.930, T_max = 0.996	k = −21→21
16577 measured reflections	l = −17→17

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) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0698P)² + 0.3682P] where P = (F_o² + 2F_c²)/3
3704 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₆H₁₄N₂O₂	V = 1281.17 (16) Å³
M_r = 266.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5250 (6) Å	µ = 0.09 mm⁻¹
b = 15.4643 (12) Å	T = 100 K
c = 12.3982 (7) Å	0.79 × 0.06 × 0.05 mm
β = 117.377 (4)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	3704 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2843 reflections with I > 2σ(I)
T_min = 0.930, T_max = 0.996	R_int = 0.041
16577 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.45 e Å⁻³
3704 reflections	Δρ_min = −0.23 e Å⁻³
237 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 s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.20289 (17)	1.11942 (6)	0.64493 (8)	0.0209 (2)
O2	0.24094 (15)	0.97368 (6)	0.30327 (8)	0.0173 (2)
N1	0.24292 (17)	1.04190 (6)	0.47613 (9)	0.0152 (2)
N2	0.21030 (18)	0.99921 (7)	0.18571 (9)	0.0182 (2)
C1	0.2410 (2)	1.04273 (7)	0.70239 (11)	0.0150 (2)
C2	0.2479 (2)	1.04255 (8)	0.81837 (11)	0.0179 (3)
C3	0.2877 (2)	0.96778 (8)	0.88407 (11)	0.0172 (3)
C4	0.3177 (2)	0.88841 (8)	0.83642 (11)	0.0149 (2)
C5	0.3597 (2)	0.81113 (8)	0.90574 (12)	0.0184 (3)
C6	0.3833 (2)	0.73399 (8)	0.85954 (12)	0.0201 (3)
C7	0.3626 (2)	0.73093 (8)	0.74058 (12)	0.0207 (3)
C8	0.3253 (2)	0.80526 (8)	0.67215 (12)	0.0177 (3)
C9	0.30404 (19)	0.88660 (7)	0.71809 (11)	0.0141 (2)
C10	0.26908 (19)	0.96648 (7)	0.65075 (11)	0.0138 (2)
C11	0.2611 (2)	0.96861 (8)	0.53223 (11)	0.0148 (2)
C12	0.2289 (2)	1.04637 (7)	0.36180 (11)	0.0146 (2)
C13	0.1957 (2)	1.11763 (7)	0.29069 (11)	0.0140 (2)
C14	0.18303 (19)	1.08332 (8)	0.18048 (11)	0.0151 (2)
C15	0.1393 (2)	1.13268 (9)	0.06759 (12)	0.0201 (3)
C16	0.1737 (2)	1.20938 (8)	0.31960 (12)	0.0175 (3)
H2A	0.222 (3)	1.0979 (12)	0.8512 (16)	0.029 (5)*
H3A	0.290 (3)	0.9681 (11)	0.9648 (16)	0.024 (4)*
H5A	0.375 (3)	0.8132 (11)	0.9894 (16)	0.027 (4)*
H6A	0.416 (3)	0.6822 (12)	0.9078 (16)	0.027 (4)*
H7A	0.376 (3)	0.6775 (12)	0.7059 (16)	0.029 (5)*
H8A	0.309 (3)	0.8009 (11)	0.5908 (15)	0.022 (4)*
H11A	0.272 (3)	0.9140 (11)	0.4942 (15)	0.026 (4)*
H15A	0.091 (3)	1.0970 (12)	0.0011 (17)	0.032 (5)*
H15B	0.256 (3)	1.1642 (14)	0.0772 (18)	0.043 (6)*
H15C	0.034 (3)	1.1763 (14)	0.0517 (18)	0.043 (6)*
H16A	0.202 (3)	1.2197 (12)	0.4021 (18)	0.036 (5)*
H16B	0.263 (4)	1.2459 (16)	0.302 (2)	0.053 (6)*
H16C	0.041 (4)	1.2329 (14)	0.266 (2)	0.047 (6)*
H1O1	0.207 (4)	1.1091 (15)	0.569 (2)	0.055 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0339 (6)	0.0115 (4)	0.0197 (4)	0.0004 (4)	0.0144 (4)	0.0013 (3)
O2	0.0244 (5)	0.0130 (4)	0.0163 (4)	0.0015 (4)	0.0109 (4)	0.0002 (3)
N1	0.0175 (5)	0.0146 (5)	0.0133 (5)	0.0000 (4)	0.0069 (4)	0.0012 (3)
N2	0.0232 (6)	0.0186 (5)	0.0150 (5)	0.0001 (4)	0.0107 (5)	0.0001 (4)
C1	0.0173 (6)	0.0123 (5)	0.0150 (5)	−0.0015 (4)	0.0070 (5)	0.0004 (4)
C2	0.0223 (7)	0.0155 (5)	0.0166 (5)	−0.0020 (5)	0.0095 (5)	−0.0032 (4)
C3	0.0189 (6)	0.0188 (6)	0.0143 (5)	−0.0033 (5)	0.0080 (5)	−0.0013 (4)
C4	0.0135 (6)	0.0160 (5)	0.0149 (5)	−0.0009 (4)	0.0061 (5)	0.0014 (4)
C5	0.0183 (6)	0.0204 (6)	0.0170 (5)	−0.0006 (5)	0.0085 (5)	0.0046 (4)
C6	0.0193 (6)	0.0171 (6)	0.0246 (6)	0.0001 (5)	0.0106 (5)	0.0063 (5)
C7	0.0240 (7)	0.0147 (6)	0.0261 (6)	0.0033 (5)	0.0139 (6)	0.0029 (5)
C8	0.0218 (7)	0.0146 (5)	0.0199 (6)	0.0017 (5)	0.0123 (5)	0.0007 (4)
C9	0.0141 (6)	0.0137 (5)	0.0150 (5)	0.0004 (4)	0.0072 (5)	0.0013 (4)
C10	0.0148 (6)	0.0125 (5)	0.0144 (5)	0.0000 (4)	0.0068 (5)	0.0003 (4)
C11	0.0151 (6)	0.0139 (5)	0.0153 (5)	0.0004 (5)	0.0069 (5)	0.0004 (4)
C12	0.0158 (6)	0.0141 (5)	0.0132 (5)	−0.0011 (5)	0.0062 (5)	−0.0014 (4)
C13	0.0147 (6)	0.0136 (5)	0.0139 (5)	−0.0009 (4)	0.0066 (5)	−0.0003 (4)
C14	0.0142 (6)	0.0166 (5)	0.0152 (5)	−0.0005 (5)	0.0073 (5)	0.0001 (4)
C15	0.0244 (7)	0.0220 (6)	0.0153 (6)	−0.0011 (6)	0.0105 (5)	0.0017 (5)
C16	0.0216 (7)	0.0130 (5)	0.0175 (6)	0.0006 (5)	0.0085 (5)	0.0001 (4)

Geometric parameters (Å, º) top

O1—C1	1.3448 (14)	C6—H6A	0.962 (18)
O1—H1O1	0.97 (2)	C7—C8	1.3787 (17)
O2—C12	1.3635 (14)	C7—H7A	0.957 (19)
O2—N2	1.4229 (13)	C8—C9	1.4198 (16)
N1—C11	1.3036 (15)	C8—H8A	0.962 (17)
N1—C12	1.3739 (15)	C9—C10	1.4457 (16)
N2—C14	1.3138 (16)	C10—C11	1.4431 (16)
C1—C10	1.4033 (16)	C11—H11A	0.989 (18)
C1—C2	1.4147 (17)	C12—C13	1.3607 (16)
C2—C3	1.3659 (17)	C13—C14	1.4274 (16)
C2—H2A	1.004 (19)	C13—C16	1.4912 (16)
C3—C4	1.4245 (17)	C14—C15	1.4920 (17)
C3—H3A	0.991 (18)	C15—H15A	0.916 (19)
C4—C5	1.4203 (17)	C15—H15B	0.96 (2)
C4—C9	1.4231 (16)	C15—H15C	0.99 (2)
C5—C6	1.3696 (19)	C16—H16A	0.96 (2)
C5—H5A	0.990 (18)	C16—H16B	0.98 (3)
C6—C7	1.4108 (19)	C16—H16C	0.98 (2)

C1—O1—H1O1	105.9 (14)	C8—C9—C10	123.34 (11)
C12—O2—N2	107.29 (9)	C4—C9—C10	119.09 (11)
C11—N1—C12	122.26 (10)	C1—C10—C11	120.06 (10)
C14—N2—O2	105.86 (9)	C1—C10—C9	118.69 (11)
O1—C1—C10	122.65 (11)	C11—C10—C9	121.25 (10)
O1—C1—C2	116.06 (10)	N1—C11—C10	120.54 (11)
C10—C1—C2	121.28 (11)	N1—C11—H11A	120.0 (10)
C3—C2—C1	120.22 (11)	C10—C11—H11A	119.5 (10)
C3—C2—H2A	120.6 (10)	C13—C12—O2	111.11 (10)
C1—C2—H2A	119.2 (10)	C13—C12—N1	127.84 (11)
C2—C3—C4	121.00 (11)	O2—C12—N1	121.01 (10)
C2—C3—H3A	119.7 (10)	C12—C13—C14	103.35 (10)
C4—C3—H3A	119.3 (10)	C12—C13—C16	128.48 (11)
C5—C4—C9	119.85 (11)	C14—C13—C16	128.16 (11)
C5—C4—C3	120.52 (11)	N2—C14—C13	112.37 (11)
C9—C4—C3	119.63 (11)	N2—C14—C15	120.98 (11)
C6—C5—C4	121.03 (12)	C13—C14—C15	126.63 (11)
C6—C5—H5A	119.4 (10)	C14—C15—H15A	111.2 (12)
C4—C5—H5A	119.5 (10)	C14—C15—H15B	110.3 (12)
C5—C6—C7	119.55 (12)	H15A—C15—H15B	112.1 (18)
C5—C6—H6A	120.8 (11)	C14—C15—H15C	110.3 (12)
C7—C6—H6A	119.7 (11)	H15A—C15—H15C	106.4 (16)
C8—C7—C6	120.58 (12)	H15B—C15—H15C	106.3 (18)
C8—C7—H7A	118.5 (11)	C13—C16—H16A	114.9 (11)
C6—C7—H7A	120.9 (11)	C13—C16—H16B	109.5 (14)
C7—C8—C9	121.36 (12)	H16A—C16—H16B	107.7 (18)
C7—C8—H8A	118.6 (10)	C13—C16—H16C	112.3 (13)
C9—C8—H8A	120.0 (10)	H16A—C16—H16C	108.8 (19)
C8—C9—C4	117.57 (11)	H16B—C16—H16C	102.8 (19)

C12—O2—N2—C14	0.20 (14)	C8—C9—C10—C1	177.05 (13)
O1—C1—C2—C3	−179.34 (12)	C4—C9—C10—C1	−2.75 (19)
C10—C1—C2—C3	1.7 (2)	C8—C9—C10—C11	−2.4 (2)
C1—C2—C3—C4	−1.7 (2)	C4—C9—C10—C11	177.78 (12)
C2—C3—C4—C5	179.74 (13)	C12—N1—C11—C10	−178.04 (12)
C2—C3—C4—C9	−0.7 (2)	C1—C10—C11—N1	5.2 (2)
C9—C4—C5—C6	−1.5 (2)	C9—C10—C11—N1	−175.36 (12)
C3—C4—C5—C6	178.15 (13)	N2—O2—C12—C13	−1.01 (15)
C4—C5—C6—C7	−0.9 (2)	N2—O2—C12—N1	176.88 (12)
C5—C6—C7—C8	2.1 (2)	C11—N1—C12—C13	175.02 (14)
C6—C7—C8—C9	−0.8 (2)	C11—N1—C12—O2	−2.5 (2)
C7—C8—C9—C4	−1.5 (2)	O2—C12—C13—C14	1.33 (15)
C7—C8—C9—C10	178.66 (13)	N1—C12—C13—C14	−176.38 (13)
C5—C4—C9—C8	2.64 (19)	O2—C12—C13—C16	−179.77 (13)
C3—C4—C9—C8	−176.96 (12)	N1—C12—C13—C16	2.5 (2)
C5—C4—C9—C10	−177.54 (12)	O2—N2—C14—C13	0.64 (15)
C3—C4—C9—C10	2.85 (19)	O2—N2—C14—C15	−177.96 (12)
O1—C1—C10—C11	1.1 (2)	C12—C13—C14—N2	−1.23 (16)
C2—C1—C10—C11	179.96 (13)	C16—C13—C14—N2	179.86 (13)
O1—C1—C10—C9	−178.36 (12)	C12—C13—C14—C15	177.28 (13)
C2—C1—C10—C9	0.5 (2)	C16—C13—C14—C15	−1.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.97 (2)	1.66 (3)	2.5471 (15)	150 (2)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂O₂
M_r	266.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.5250 (6), 15.4643 (12), 12.3982 (7)
β (°)	117.377 (4)
V (Å³)	1281.17 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.79 × 0.06 × 0.05

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.930, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	16577, 3704, 2843
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.134, 1.05
No. of reflections	3704
No. of parameters	237
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.23

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
O1—H1O1···N1	0.97 (2)	1.66 (3)	2.5471 (15)	150 (2)

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§On secondment to: The Center of Excellence for Advanced Materials Research, King Abdu Aziz University, Jeddah 21589, Saudi Arabia.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. MH thanks Universiti Sains Malaysia for a post-doctoral research fellowship. AMA and SAK thank the Chemistry Department, King Abdul Aziz University, Jeddah, for providing research facilities. AMA would also like to thank the deanship of scientific research at KAU for the financial grant No. 171/428.

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