Crystal structure of (E)-2-hy­droxy-4′-meth­oxy­aza­stilbene

Chantrapromma, S.; Kaewmanee, N.; Boonnak, N.; Chantrapromma, K.; Ghabbour, H.A.; Fun, H.-K.

doi:10.1107/S2056989015008348

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ISSN: 2056-9890

Volume 71| Part 6| June 2015| Pages 571-573

doi:10.1107/S2056989015008348

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Crystal structure of (E)-2-hydroxy-4′-methoxyazastilbene

Suchada Chantrapromma,^a ^*‡ Narissara Kaewmanee,^a Nawong Boonnak,^b Kan Chantrapromma,^c Hazem A. Ghabbour ^d and Hoong-Kun Fun ^d,^e §

^aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^bDepartment of Chemistry, Faculty of Science, Thaksin University, Phapayom, Phatthalung 93110, Thailand, ^cFaculty of Science and Technology, Hatyai University, Hat-Yai, Songkhla 90110, Thailand, ^dDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Kingdom of Saudi Arabia, and ^eX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 20 April 2015; accepted 28 April 2015; online 7 May 2015)

The title azastilbene derivative, C₁₄H₁₃NO₂ {systematic name: (E)-2-[(4-methoxybenzylidene)amino]phenol}, is a product of the condensation reaction between 4-methoxybenzaldehyde and 2-aminophenol. The molecule adopts an E conformation with respect to the azomethine C=N bond and is almost planar, the dihedral angle between the two substituted benzene rings being 3.29 (4)°. The methoxy group is coplanar with the benzene ring to which it is attached, the C_methyl—O—C—C torsion angle being −1.14 (12)°. There is an intramolecular O—H⋯N hydrogen bond generating an S(5) ring motif. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming zigzag chains along [10-1]. The chains are linked via C—H⋯π interactions, forming a three-dimensional structure.

Keywords: crystal structure; azastilbene; antibacterial; anti-oxidant; hydrogen bonding.

CCDC reference: 1062128

1. Chemical context

Azastilbenes have been reported to possess various biological activities such as antibacterial (Tamizh et al., 2012 ), anti-oxidant (Cheng et al., 2010 ; Lu et al., 2012 ), antifungal (da Silva et al., 2011 ) and antiproliferative (Fujita et al., 2012 ) including lipoxygenase inhibitor (Aslam et al., 2012b ) activities. Pd^II and Ru^III complexes of azastilbenes have been synthesized and some have shown potent antibacterial activity (Briel et al., 1998 ; Prabhakaran et al., 2008 ; Puthilibai et al., 2009 ). The interesting biological activities of azastilbenes have attracted us to synthesis a series of azastilbenes, including the title compound, and to study their antibacterial and anti-oxidant activities (Kaewmanee et al., 2013 , 2014 ). The antibacterial assay for the title compound indicated that it possesses moderate to weak antibacterial activity against B. subtilis, S. aureus, P. aeruginosa, S. typhi and S. sonnei with the MIC values in the range of 37.5 to 150 µg/ml. In addition, it also shows interesting antioxidant activity by DPPH assay with the IC₅₀ value of 0.080±0.0004 µg/ml. Herein, we report on the synthesis, spectroscopic and crystallographic characterization of the title compound.

2. Structural commentary

The title azastilbene compound (Fig. 1) has an E conformation about the azomethine C7=N1 double bond [1.2825 (10) Å], the C8—N1—C7—C1 torsion angle being −178.67 (8)°. The molecule is almost planar with a dihedral angle of 3.29 (4)° between the two substituted benzene rings. The methoxy group is co-planar with the benzene ring to which it is attached, the C14—O1—C4—C5 torsion angle being −1.14 (12)°. There is an intramolecular O—H⋯N hydrogen bond (Fig. 1 and Table 1) that generates an S(5) ring motif. The bond lengths are comparable with those found for some closely related structures (Habibi et al., 2013 ; Aslam et al., 2012a ; Kaewmanee et al., 2013, 2014; Sun et al., 2011 ).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of rings C1–C6 and C8–C13, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N1	0.774 (18)	2.078 (17)	2.6315 (11)	128.7 (17)
C14—H14B⋯O2ⁱ	0.96	2.71	3.2876 (12)	119
C2—H2A⋯Cg2ⁱⁱ	0.93	2.93	3.5662 (9)	127
C13—H13A⋯Cg1ⁱⁱⁱ	0.93	2.76	3.4671 (9)	134
Symmetry codes: (i) $[x-1, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[x, -y, z+{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 60% probability level. The intramolecular O—H⋯N hydrogen bond is shown as a dashed line (see Table 1

3. Supramolecular features

In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming zigzag chains along [10 $[\overline{1}]$ ] (Fig. 2 and Table 1). The chains are linked via C—H⋯π interactions (Fig. 3 and Table 1), forming a three-dimensional structure.

Figure 2
A view along the b axis of the crystal packing of the title compound. The C—H⋯O hydrogen bonds are shown as dashed lines (see Table 1

for details).

Figure 3
A view of the C—H⋯π interactions (dashed lines) in the crystal of the title compound (see Table 1

for details; ring centroids are shown as coloured spheres).

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.36; Groom & Allen, 2014 ) for azastilbenes gave over 2800 hits. A search for 2-(benzylideneamino)phenols gave 78 hits, and for 2-[(4-methoxybenzylidene)amino]phenols there were five hits. In the compound that most closely resembles the title compound, namely 5-{[(2-hydroxyphenyl)imino]methyl}-2-methoxyphenol (Habibi et al., 2013), the two aromatic rings are inclined to one another by ca 16.9°.

5. Synthesis and crystallization

A solution of 4-methoxybenzaldehyde (2.5 mmol, 0.37 g) in water (20 ml) and 2-aminophenol (2.5 mmol, 0.25 g) in water (20 ml) were mixed and stirred at room temperature for around 8 h until a white precipitate appeared. The resulting white solid was filtered, washed several times with cold ethanol and then dried in vacuo overnight to yield the desired azastilbene (430 mg, 76% yield). Colourless block-shaped crystals, suitable for X-ray structure analysis, were obtained by recrystallization from methanol by slow evaporation at room temperature after several days (m.p. 388–390 K).

UV–Vis (CH₃OH) λ_max (log∊): 275 (1.93), 340 (0.61) nm; FT–IR (KBr) ν: 3337, 1595, 1510, 1248, 1027 cm⁻¹.; ¹H NMR (300 MHz, DMSO-d₆) δ, p.p.m.: 8.87 (s, 1H), 8.61 (s, 1H), 7.98 (d, J = 8.7 Hz, 2H), 7.18 (dd, J = 7.5, 1.2 Hz, 1H), 7.06 (d, J = 8.7 Hz, 2H), 7.03 (td, J = 7.5, 1.2 Hz, 1H), 6.83 (td, J = 7.5, 1.2 Hz, 1H), 6.09 (dd, J = 7.5, 1.2 Hz, 1H), 3.84 (s, –OCH₃). The UV–Vis spectroscopic data showed absorption bands of an azastilbene (275 and 340 nm) while the FT–IR spectrum exhibited the stretching vibrations of O—H (3337 cm⁻¹), C=N (1595 cm⁻¹), C=C (1510 cm⁻¹), C—N (1248 cm⁻1) and C—O (1027 cm⁻¹). The successful synthesis was also supported by the ¹H NMR spectroscopic data, which showed the characteristic signals of an olefinic proton at 8.61 (s, 1H) and para-substituted aromatic protons at 7.98 (d, J = 8.7 Hz, 2H) and 7.06 (d, J = 8.7 Hz, 2H), respectively. Moreover the ¹H NMR spectrum also showed typical signals of ortho-substituted aromatic protons at 7.18 (dd, J = 7.5, 1.2 Hz, 1H), 7.03 (td, J = 7.5, 1.2 Hz, 1H), 6.83 (td, J = 7.5, 1.2 Hz, 1H) and 6.09 (dd, J = 7.5, 1.2 Hz, 1H) and a methoxy proton at 3.84 (s, –OCH₃).

The antibacterial activity investigation of the title compound against Gram-positive bacteria, which are B. subtilis, S. aureus, MRSA and E. faecalis, and Gram-negative bacteria, which are P. aeruginosa, S. sonnei and S. typhi, showed moderate, mild or no inhibition. The most interesting antibacterial activity showed moderate activity against P. aeruginosa with an MIC value of 37.5 µg/ml.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The OH H atom was located in a difference Fourier map and freely refined. The C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms: C—H = 0.93–0.96 Å with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₂
M_r	227.25
Crystal system, space group	Monoclinic, Pc
Temperature (K)	100
a, b, c (Å)	8.0357 (3), 5.5554 (2), 12.8733 (5)
β (°)	101.312 (1)
V (Å³)	563.52 (4)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.55 × 0.48 × 0.41

Data collection
Diffractometer	Bruker APEXII D8 Venture
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.953, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	26314, 3449, 3414
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.100, 1.09
No. of reflections	3449
No. of parameters	160
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.28
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ), Mercury (Macrae et al., 2008 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1062128

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015008348/su5124sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015008348/su5124Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015008348/su5124Isup3.cml

checkCIF report

Chemical context top

Azastilbenes have been reported to possess various biological activities such as antibacterial (Tamizh et al., 2012), anti-oxidant (Cheng et al., 2010; Lu et al., 2012), antifungal (da Silva et al., 2011) and antiproliferative (Fujita et al., 2012) including lipoxygenase inhibitor (Aslam et al., 2012b) activities. Pd^II and Ru^III complexes of azastilbenes have been synthesized and some have shown potent antibacterial activity (Briel et al., 1998; Prabhakaran et al., 2008; Puthilibai et al., 2009). The interesting biological activities of azastilbenes have attracted us to synthesis a series of azastilbenes, including the title compound, and to study their antibacterial and anti-oxidant activities (Kaewmanee et al., 2013, 2014). The antibacterial assay for the title compound indicated that it possesses moderate to weak antibacterial activity against B. subtilis, S. aureus, P. aeruginosa, S. typhi and S. sonnei with the MIC values in the range of 37.5 to 150 µg/ml. In addition, it also shows interesting antioxidant activity by DPPH assay with the IC₅₀ value of 0.080±0.0004 µg/ml. Herein, we report on the synthesis and spectroscopic and crystallographic characterization of the title compound.

Structural commentary top

The title azastilbene compound (Fig. 1) has an E conformation about the azomethine C7═N1 double bond [1.2825 (10) Å], the C8—N1—C7—C1 torsion angle being -178.67 (8)°. The molecule is almost planar with a dihedral angle of 3.29 (4)° between the two substituted benzene rings. The methoxy group is co-planar with the benzene ring to which it is attached, the C14—O1—C4—C5 torsion angle being -1.14 (12)°. There is an intramolecular O—H···N hydrogen bond (Fig. 1 and Table 1) that generates an S(5) ring motif. The bond lengths are comparable with those found for some closely related structures (Habibi et al., 2013; Aslam et al., 2012a; Kaewmanee et al., 2013, 2014; Sun et al., 2011).

Supramolecular features top

In the crystal, molecules are linked via C—H···O hydrogen bonds, forming zigzag chains along [101] (Fig. 2 and Table 1). The chains are linked via C—H···π interactions (Fig. 3 and Table 1), forming a three-dimensional structure.

Database survey top

A search of the Cambridge Structural Database (CSD, Version 5.36; Groom & Allen, 2014) for azastilbenes gave over 2800 hits. A search for 2-(benzylideneamino)phenols gave 78 hits, and for 2-[(4-methoxybenzylidene)amino]phenols there were five hits. In the compound that most closely resembles the title compound, namely 5-{[(2-hydroxyphenyl)imino]methyl}-2-methoxyphenol (Habibi et al., 2013), the two aromatic rings are inclined to one another by ca 16.9°.

Synthesis and crystallization top

UV–Vis (CH₃OH) λ_max (logε): 275 (1.93), 340 (0.61) nm.; FT–IR (KBr) ν: 3337, 1595, 1510, 1248, 1027 cm^-1.; ¹H NMR (300 MHz, DMSO-d₆) δ, p.p.m.: 8.87 (s, 1H), 8.61 (s, 1H), 7.98 (d, J = 8.7 Hz, 2H), 7.18 (dd, J = 7.5, 1.2 Hz, 1H), 7.06 (d, J = 8.7 Hz, 2H), 7.03 (td, J = 7.5, 1.2 Hz, 1H), 6.83 (td, J = 7.5, 1.2 Hz, 1H), 6.09 (dd, J = 7.5, 1.2 Hz, 1H), 3.84 (s, –OCH₃). The UV–Vis spectroscopic data showed absorption bands of an azastilbene (275 and 340 nm) while the FT–IR spectrum exhibited the stretching vibrations of O—H (3337 cm^-1), C═N (1595 cm^-1), C═C (1510 cm^-1), C—N (1248 cm^-1) and C—O (1027 cm^-1). The successfully synthesis was also supported by the ¹H NMR spectroscopic data, which showed the characteristic signals of an olefinic proton at 8.61 (s, 1H) and para-substituted aromatic protons at 7.98 (d, J = 8.7 Hz, 2H) and 7.06 (d, J = 8.7 Hz, 2H), respectively. Moreover the ¹H NMR spectrum also showed typical signals of ortho-substituted aromatic protons at 7.18 (dd, J = 7.5, 1.2 Hz, 1H), 7.03 (td, J = 7.5, 1.2 Hz, 1H), 6.83 (td, J = 7.5, 1.2 Hz, 1H) and 6.09 (dd, J = 7.5, 1.2 Hz, 1H) and a methoxy proton at 3.84 (s, –OCH₃).

The antibacterial activity investigation of the title compound against Gram-positive bacteria, which are B. subtilis, S. aureus, MRSA, E. faecalis, and Gram-negative bacteria, which are P. aeruginosa, S. sonnei and S. typhi, showed moderate, mild or no inhibition. The most interesting antibacterial activity showed moderate activity against P. aeruginosa with an MIC value of 37.5 µg/ml.

Refinement top

Related literature top

For related literature, see: Aslam et al. (2012a, 2012b); Briel et al. (1998); Cheng et al. (2010); Fujita et al. (2012); Groom & Allen (2014); Habibi et al. (2013); Kaewmanee et al. (2013, 2014); Lu et al. (2012); Prabhakaran et al. (2008); Puthilibai et al. (2009); da Silva et al. (2011); Sun et al. (2011); Tamizh et al. (2012).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 60% probability level.
	Fig. 2. A view along the b axis of the crystal packing of the title compound. The C—H···O hydrogen bonds are shown as dashed lines (see Table 1 for details).
	Fig. 3. A view of the C—H···π interactions (dashed lines) in the crystal of the title compound (see Table 1 for details; ring centroids are shown as coloured spheres).

(E)-2-[(4-Methoxybenzylidene)amino]phenol top

Crystal data top

C₁₄H₁₃NO₂	D_x = 1.339 Mg m⁻³
M_r = 227.25	Melting point = 388–390 K
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
a = 8.0357 (3) Å	Cell parameters from 3449 reflections
b = 5.5554 (2) Å	θ = 2.6–30.5°
c = 12.8733 (5) Å	µ = 0.09 mm⁻¹
β = 101.312 (1)°	T = 100 K
V = 563.52 (4) Å³	Block, colorless
Z = 2	0.55 × 0.48 × 0.41 mm
F(000) = 240

Data collection top

Bruker APEXII D8 Venture diffractometer	3414 reflections with I > 2σ(I)
ϕ and ω scans	R_int = 0.023
Absorption correction: multi-scan (SADABS; Bruker, 2009)	θ_max = 30.5°, θ_min = 2.6°
T_min = 0.953, T_max = 0.964	h = −11→11
26314 measured reflections	k = −7→7
3449 independent reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0786P)² + 0.0298P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
3449 reflections	Δρ_max = 0.37 e Å⁻³
160 parameters	Δρ_min = −0.28 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.054 (8)

Crystal data top

C₁₄H₁₃NO₂	V = 563.52 (4) Å³
M_r = 227.25	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 8.0357 (3) Å	µ = 0.09 mm⁻¹
b = 5.5554 (2) Å	T = 100 K
c = 12.8733 (5) Å	0.55 × 0.48 × 0.41 mm
β = 101.312 (1)°

Data collection top

Bruker APEXII D8 Venture diffractometer	3449 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3414 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.964	R_int = 0.023
26314 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	2 restraints
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.37 e Å⁻³
3449 reflections	Δρ_min = −0.28 e Å⁻³
160 parameters

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.29289 (8)	0.08802 (12)	0.07528 (5)	0.01815 (14)
O2	0.92146 (10)	0.70962 (12)	0.58775 (6)	0.02323 (15)
H1O2	0.859 (2)	0.653 (3)	0.5407 (15)	0.028 (3)*
N1	0.72131 (9)	0.33548 (14)	0.53665 (5)	0.01630 (16)
C1	0.54115 (10)	0.13926 (16)	0.38967 (6)	0.01455 (16)
C2	0.55623 (10)	0.31817 (15)	0.31478 (7)	0.01598 (16)
H2A	0.6239	0.4524	0.3353	0.019*
C3	0.47132 (10)	0.29620 (15)	0.21094 (7)	0.01586 (16)
H3A	0.4826	0.4149	0.1618	0.019*
C4	0.36790 (10)	0.09459 (15)	0.17945 (6)	0.01416 (16)
C5	0.35026 (11)	−0.08418 (16)	0.25290 (6)	0.01607 (17)
H5A	0.2812	−0.2171	0.2326	0.019*
C6	0.43785 (11)	−0.05985 (16)	0.35704 (6)	0.01649 (16)
H6A	0.4273	−0.1791	0.4061	0.020*
C7	0.63122 (10)	0.15284 (17)	0.49969 (6)	0.01611 (17)
H7A	0.6229	0.0242	0.5446	0.019*
C8	0.81013 (9)	0.34278 (15)	0.64262 (6)	0.01427 (16)
C9	0.91560 (10)	0.54613 (15)	0.66557 (6)	0.01633 (16)
C10	1.01507 (11)	0.57944 (17)	0.76609 (7)	0.01860 (17)
H10A	1.0854	0.7133	0.7803	0.022*
C11	1.00837 (11)	0.41075 (16)	0.84506 (7)	0.01799 (17)
H11A	1.0752	0.4309	0.9122	0.022*
C12	0.90092 (10)	0.21016 (17)	0.82364 (6)	0.01711 (16)
H12A	0.8951	0.0994	0.8770	0.021*
C13	0.80332 (10)	0.17641 (15)	0.72308 (6)	0.01595 (16)
H13A	0.7331	0.0424	0.7092	0.019*
C14	0.19195 (12)	−0.11830 (17)	0.03898 (7)	0.02058 (18)
H14A	0.1551	−0.1096	−0.0365	0.031*
H14B	0.0948	−0.1225	0.0720	0.031*
H14C	0.2582	−0.2615	0.0570	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0188 (3)	0.0212 (3)	0.0130 (3)	−0.0025 (2)	−0.0003 (2)	−0.0004 (2)
O2	0.0342 (3)	0.0193 (3)	0.0161 (3)	−0.0091 (3)	0.0045 (2)	0.0009 (2)
N1	0.0173 (3)	0.0180 (4)	0.0132 (3)	−0.0009 (2)	0.0019 (3)	−0.0010 (2)
C1	0.0157 (4)	0.0152 (3)	0.0125 (3)	−0.0003 (3)	0.0023 (3)	−0.0016 (3)
C2	0.0172 (4)	0.0142 (3)	0.0162 (4)	−0.0019 (3)	0.0024 (3)	−0.0010 (3)
C3	0.0170 (3)	0.0146 (3)	0.0155 (3)	−0.0005 (3)	0.0021 (3)	0.0013 (3)
C4	0.0133 (3)	0.0159 (4)	0.0132 (4)	0.0003 (3)	0.0026 (3)	−0.0010 (2)
C5	0.0177 (3)	0.0163 (4)	0.0142 (4)	−0.0031 (3)	0.0030 (3)	−0.0013 (3)
C6	0.0208 (4)	0.0158 (3)	0.0131 (3)	−0.0027 (3)	0.0039 (3)	−0.0002 (3)
C7	0.0176 (4)	0.0178 (4)	0.0131 (3)	−0.0008 (3)	0.0032 (3)	−0.0013 (3)
C8	0.0148 (3)	0.0150 (3)	0.0131 (3)	−0.0002 (3)	0.0029 (3)	−0.0014 (3)
C9	0.0183 (4)	0.0166 (3)	0.0148 (3)	−0.0022 (3)	0.0050 (3)	−0.0013 (3)
C10	0.0188 (4)	0.0196 (4)	0.0174 (3)	−0.0040 (3)	0.0036 (3)	−0.0042 (3)
C11	0.0172 (3)	0.0220 (4)	0.0141 (3)	−0.0008 (3)	0.0013 (3)	−0.0030 (3)
C12	0.0179 (4)	0.0184 (4)	0.0147 (4)	−0.0001 (3)	0.0025 (3)	0.0006 (3)
C13	0.0172 (3)	0.0162 (4)	0.0141 (4)	−0.0016 (3)	0.0023 (3)	−0.0005 (3)
C14	0.0194 (4)	0.0224 (4)	0.0178 (4)	−0.0031 (3)	−0.0015 (3)	−0.0028 (3)

Geometric parameters (Å, º) top

O1—C4	1.3586 (9)	C6—H6A	0.9300
O1—C14	1.4287 (10)	C7—H7A	0.9300
O2—C9	1.3599 (11)	C8—C13	1.3973 (11)
O2—H1O2	0.772 (19)	C8—C9	1.4084 (11)
N1—C7	1.2825 (10)	C9—C10	1.3935 (11)
N1—C8	1.4107 (10)	C10—C11	1.3915 (13)
C1—C6	1.3972 (11)	C10—H10A	0.9300
C1—C2	1.4065 (11)	C11—C12	1.4035 (12)
C1—C7	1.4605 (10)	C11—H11A	0.9300
C2—C3	1.3818 (11)	C12—C13	1.3884 (11)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.4062 (11)	C13—H13A	0.9300
C3—H3A	0.9300	C14—H14A	0.9600
C4—C5	1.3975 (11)	C14—H14B	0.9600
C5—C6	1.3932 (11)	C14—H14C	0.9600
C5—H5A	0.9300

C4—O1—C14	117.25 (7)	C13—C8—C9	118.98 (7)
C9—O2—H1O2	101.3 (12)	C13—C8—N1	127.73 (7)
C7—N1—C8	121.55 (7)	C9—C8—N1	113.29 (7)
C6—C1—C2	118.64 (7)	O2—C9—C10	119.93 (8)
C6—C1—C7	118.99 (7)	O2—C9—C8	119.18 (7)
C2—C1—C7	122.36 (7)	C10—C9—C8	120.88 (7)
C3—C2—C1	120.54 (7)	C11—C10—C9	119.45 (8)
C3—C2—H2A	119.7	C11—C10—H10A	120.3
C1—C2—H2A	119.7	C9—C10—H10A	120.3
C2—C3—C4	120.07 (8)	C10—C11—C12	120.11 (8)
C2—C3—H3A	120.0	C10—C11—H11A	119.9
C4—C3—H3A	120.0	C12—C11—H11A	119.9
O1—C4—C5	124.37 (7)	C13—C12—C11	120.24 (8)
O1—C4—C3	115.38 (7)	C13—C12—H12A	119.9
C5—C4—C3	120.24 (7)	C11—C12—H12A	119.9
C6—C5—C4	118.88 (7)	C12—C13—C8	120.31 (8)
C6—C5—H5A	120.6	C12—C13—H13A	119.8
C4—C5—H5A	120.6	C8—C13—H13A	119.8
C5—C6—C1	121.63 (8)	O1—C14—H14A	109.5
C5—C6—H6A	119.2	O1—C14—H14B	109.5
C1—C6—H6A	119.2	H14A—C14—H14B	109.5
N1—C7—C1	122.48 (7)	O1—C14—H14C	109.5
N1—C7—H7A	118.8	H14A—C14—H14C	109.5
C1—C7—H7A	118.8	H14B—C14—H14C	109.5

C6—C1—C2—C3	−0.41 (12)	C2—C1—C7—N1	4.45 (12)
C7—C1—C2—C3	178.77 (7)	C7—N1—C8—C13	−6.46 (13)
C1—C2—C3—C4	0.40 (12)	C7—N1—C8—C9	173.81 (7)
C14—O1—C4—C5	−1.14 (12)	C13—C8—C9—O2	−179.42 (8)
C14—O1—C4—C3	177.64 (7)	N1—C8—C9—O2	0.34 (11)
C2—C3—C4—O1	−178.73 (7)	C13—C8—C9—C10	1.49 (12)
C2—C3—C4—C5	0.10 (12)	N1—C8—C9—C10	−178.75 (7)
O1—C4—C5—C6	178.14 (7)	O2—C9—C10—C11	−179.85 (8)
C3—C4—C5—C6	−0.58 (12)	C8—C9—C10—C11	−0.77 (13)
C4—C5—C6—C1	0.57 (13)	C9—C10—C11—C12	−0.61 (14)
C2—C1—C6—C5	−0.09 (13)	C10—C11—C12—C13	1.27 (13)
C7—C1—C6—C5	−179.29 (7)	C11—C12—C13—C8	−0.54 (13)
C8—N1—C7—C1	−178.67 (8)	C9—C8—C13—C12	−0.82 (12)
C6—C1—C7—N1	−176.38 (8)	N1—C8—C13—C12	179.45 (7)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of rings C1–C6 and C8–C13, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N1	0.774 (18)	2.078 (17)	2.6315 (11)	128.7 (17)
C14—H14B···O2ⁱ	0.96	2.71	3.2876 (12)	119
C2—H2A···Cg2ⁱⁱ	0.93	2.93	3.5662 (9)	127
C13—H13A···Cg1ⁱⁱⁱ	0.93	2.76	3.4671 (9)	134

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of rings C1–C6 and C8–C13, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N1	0.774 (18)	2.078 (17)	2.6315 (11)	128.7 (17)
C14—H14B···O2ⁱ	0.96	2.71	3.2876 (12)	119
C2—H2A···Cg2ⁱⁱ	0.93	2.93	3.5662 (9)	127
C13—H13A···Cg1ⁱⁱⁱ	0.93	2.76	3.4671 (9)	134

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₂
M_r	227.25
Crystal system, space group	Monoclinic, Pc
Temperature (K)	100
a, b, c (Å)	8.0357 (3), 5.5554 (2), 12.8733 (5)
β (°)	101.312 (1)
V (Å³)	563.52 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.55 × 0.48 × 0.41

Data collection
Diffractometer	Bruker APEXII D8 Venture diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.953, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	26314, 3449, 3414
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.100, 1.09
No. of reflections	3449
No. of parameters	160
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.28

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§Additional correspondence author, e-mail: hfun.c@ksu.edu.sa. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Department of Chemistry, Faculty of Science, Prince of Songkla University, for research facilities. The authors extend their appreciation to The Deanship of Scientific Research at King Saud University for funding this work through research group project No. RGP-VPP-207.

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Volume 71| Part 6| June 2015| Pages 571-573

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