4-(2-Methoxy­benzyl­idene)-2-phenyl-1,3-oxazol-5(4H)-one

Asiri, A.M.; Akkurt, M.; Khan, I.U.; Arshad, M.N.

doi:10.1107/S1600536809010216

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o842

doi:10.1107/S1600536809010216

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4-(2-Methoxybenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one

Abdullah Mohamed Asiri,^a Mehmet Akkurt,^b ^* Islam Ullah Khan ^c and Muhammad N. Arshad ^a

^aChemistry Department, Faculty of Science, King Abdul-Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, ^bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^cDepartment of Chemistry, Government College University, Lahore, Pakistan
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 11 March 2009; accepted 19 March 2009; online 25 March 2009)

The title molecule, C₁₇H₁₃NO₃, adopts a Z configuration about the central olefinic bond. The 2-phenyl ring is almost coplanar with the plane of the oxazolone ring system, making a dihedral angle of 2.03 (11)°. The crystal structure is stabilized by π–π interactions between the oxazolone ring and phenyl ring of a neighbouring molecule [centroid–centroid distance = 3.550 (3)Å], and by two weak intermolecular C—H⋯π interactions. In addition, the crystal structure exhibits one weak intramolecular C—H⋯N hydrogen bond.

Related literature

For general background to azalactones and their biological and pharmaceutical properties, see: Cannella et al. (1996 ); Cavelier & Verducci (1995 ); Gelmi et al. (1997 ); Gonzalez-Martinez, Puchades, Maquieira, Ferrer, Marco & Barcelo (1999 ); Gottwald & Seebach (1999 ); Mesaik et al. (2004 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₁₃NO₃
M_r = 279.28
Triclinic, $[P \overline 1]$
a = 8.8073 (6) Å
b = 9.6140 (6) Å
c = 9.8272 (6) Å
α = 66.503 (4)°
β = 67.248 (4)°
γ = 71.734 (4)°
V = 691.14 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.28 × 0.08 × 0.05 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: none
14582 measured reflections
3457 independent reflections
1464 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.133
S = 0.93
3457 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯N1	0.93	2.43	3.087 (3)	127
C17—H17A⋯Cg3ⁱ	0.96	2.81	3.682 (3)	151
C17—H17C⋯Cg2ⁱⁱ	0.96	2.96	3.832 (3)	151
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y, -z. Cg2 is the centroid of the C1–C6 benzene ring and Cg3 is the centroid of the C11—C16 phenyl ring.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010216/lx2096sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010216/lx2096Isup2.hkl

checkCIF report

Comment top

Azalactones are a class of important heterocyclic compounds and exhibit a variety of biological and pharmaceutical properties (Mesaik et al., 2004) They are also useful precursors for the synthesis of amino acids (Gottwald & Seebach, 1999), peptides (Cavelier & Verducci, 1995), heterocycles (Cannella et al., 1996), biosensors (Gonzalez-Martinez et al., 1999), and antitumoror antimicrobial compounds (Gelmi et al., 1997). Here we report the crystal structure of the title compound, 4-(2-methoxybenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one (Fig. 1).

The title molecule (Fig. 1) possesses normal geometric parameters (Allen et al., 1987) and adopts a Z configuration about the central olefinic bond. The C11–C16 phenyl ring makes a dihedral angle of 2.03 (11) ° with the plane of the oxazolone ring system. The molecular packing (Fig. 2) is stabilized by intermolecular π—π interactions between the oxazolone ring and phenyl ring of neighbouring molecules, with a Cg1···Cg3ⁱⁱⁱ distance of 3.550 (3) Å (Cg1 and Cg3 are the centroids of the O1/C10/N1/C8/C9 oxazolone ring and the C11—C16 phenyl ring; symmetry code as in Fig, 2). The crystal packing is further stabilized by two intermolecular C—H···π interactions; one between the H atom of methoxy group and the phenyl ring of a neighbouring molecule, a second between the H atom of methoxy group and the methoxyphenyl ring of an adjacent molecule, respectively (Fig. 2 and Table 1; Cg2 is the centroid of the C1–C6 benzene ring, symmetry code as in Fig, 2). Additionally, there is one intramolecular C—H···N hydrogen bond between a benzene—H atom and the N atom of oxazolone ring (Table 1 and Fig. 2).

Related literature top

For general background, see: Cannella et al. (1996); Cavelier & Verducci (1995); Gelmi et al. (1997); Gonzalez-Martinez, Puchades, Maquieira, Ferrer, Marco & Barcelo (1999); Gottwald & Seebach (1999); Mesaik et al. (2004). For bond-length data, see: Allen et al. (1987). Cg2 is the centroid of the C1–C6

benzene ring and Cg3 is the centroid of the C11—C16 phenyl ring.

Experimental top

Anhydrous sodium acetate (2.1 g, 25.3 mmol) was added to a solution of 2-methoxybenzaldehyde (3.5 g, 25.7 mmol) and hippuric acid (7.7 g, 31.1 mmol) in acetic anhydride (2.1 g, 20.6 mmol). The reaction mixture was heated to 353 K and stirred under reflux conditions for the appropriate time 2 h. The reaction mixture was cooled to room temperature and ethanol (10 ml) was added. The mixture was stirred for 10 min until a yellow solid precipitated. The mixture was allowed to stand overnight, and then it was cooled in an ice bath. The crude azalactones were obtained after filtration and washing with hot water. Recrystallization from acetone/water afforded the pure azalactones as yellow crystals. [Yield (5.79 g, 91%), m.p. 440–441 K]. IR (cm^-1) 1769 (C═O),1648 (C═C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. π—π, C—H···π and C—H···N interactions (dotted lines) in the title compound. Cg denotes the ring centroids. [Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y, -z; (iii) -x+1, -y+1, -z+1].

4-(2-Methoxybenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one top

Crystal data top

C₁₇H₁₃NO₃	Z = 2
M_r = 279.28	F(000) = 292
Triclinic, P1	D_x = 1.342 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8073 (6) Å	Cell parameters from 1969 reflections
b = 9.6140 (6) Å	θ = 2.4–22.4°
c = 9.8272 (6) Å	µ = 0.09 mm⁻¹
α = 66.503 (4)°	T = 296 K
β = 67.248 (4)°	Prism, yellow
γ = 71.734 (4)°	0.28 × 0.08 × 0.05 mm
V = 691.14 (8) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	1464 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 28.5°, θ_min = 2.4°
Detector resolution: 10.0 pixels mm^-1	h = −11→11
ϕ and ω scans	k = −12→12
14582 measured reflections	l = −13→13
3457 independent reflections

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.133	w = 1/[σ²(F_o²) + (0.0583P)²] where P = (F_o² + 2F_c²)/3
S = 0.93	(Δ/σ)_max = 0.001
3457 reflections	Δρ_max = 0.16 e Å⁻³
192 parameters	Δρ_min = −0.13 e Å⁻³
0 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: 0.008 (3)

Crystal data top

C₁₇H₁₃NO₃	γ = 71.734 (4)°
M_r = 279.28	V = 691.14 (8) Å³
Triclinic, P1	Z = 2
a = 8.8073 (6) Å	Mo Kα radiation
b = 9.6140 (6) Å	µ = 0.09 mm⁻¹
c = 9.8272 (6) Å	T = 296 K
α = 66.503 (4)°	0.28 × 0.08 × 0.05 mm
β = 67.248 (4)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1464 reflections with I > 2σ(I)
14582 measured reflections	R_int = 0.048
3457 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 0.93	Δρ_max = 0.16 e Å⁻³
3457 reflections	Δρ_min = −0.13 e Å⁻³
192 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.25166 (15)	0.44719 (14)	0.39300 (14)	0.0569 (5)
O2	0.21889 (18)	0.24891 (17)	0.34504 (18)	0.0822 (6)
O3	0.71016 (18)	0.05676 (17)	−0.02406 (16)	0.0758 (6)
N1	0.51111 (18)	0.48138 (17)	0.23057 (16)	0.0496 (6)
C1	0.7332 (2)	0.2733 (2)	0.0149 (2)	0.0506 (7)
C2	0.8036 (2)	0.1640 (2)	−0.0653 (2)	0.0585 (8)
C3	0.9578 (3)	0.1700 (3)	−0.1783 (2)	0.0728 (9)
C4	1.0418 (3)	0.2832 (3)	−0.2108 (3)	0.0812 (9)
C5	0.9784 (3)	0.3890 (3)	−0.1317 (2)	0.0741 (9)
C6	0.8245 (3)	0.3836 (2)	−0.0200 (2)	0.0613 (8)
C7	0.5675 (2)	0.2690 (2)	0.1242 (2)	0.0534 (7)
C8	0.4736 (2)	0.3592 (2)	0.2139 (2)	0.0494 (7)
C9	0.3054 (3)	0.3362 (2)	0.3179 (2)	0.0570 (8)
C10	0.3815 (2)	0.5263 (2)	0.3330 (2)	0.0469 (6)
C11	0.3562 (2)	0.6487 (2)	0.3944 (2)	0.0496 (7)
C12	0.2070 (3)	0.6867 (2)	0.5026 (2)	0.0623 (8)
C13	0.1867 (3)	0.8024 (3)	0.5607 (3)	0.0762 (9)
C14	0.3129 (4)	0.8808 (3)	0.5107 (3)	0.0779 (10)
C15	0.4617 (3)	0.8459 (3)	0.4015 (3)	0.0760 (10)
C16	0.4826 (3)	0.7300 (2)	0.3435 (2)	0.0627 (8)
C17	0.7702 (3)	−0.0552 (3)	−0.1038 (3)	0.0876 (10)
H3	1.00400	0.09810	−0.23150	0.0870*
H4	1.14440	0.28850	−0.28830	0.0970*
H5	1.03870	0.46320	−0.15340	0.0890*
H6	0.78080	0.45550	0.03320	0.0740*
H7	0.51770	0.19180	0.13430	0.0640*
H12	0.12020	0.63380	0.53610	0.0750*
H13	0.08670	0.82700	0.63400	0.0910*
H14	0.29880	0.95860	0.55060	0.0940*
H15	0.54730	0.90020	0.36740	0.0910*
H16	0.58250	0.70640	0.26970	0.0750*
H17A	0.78080	−0.00370	−0.21230	0.1310*
H17B	0.69250	−0.12400	−0.06060	0.1310*
H17C	0.87760	−0.11310	−0.09190	0.1310*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0465 (8)	0.0591 (8)	0.0597 (8)	−0.0112 (7)	−0.0015 (6)	−0.0266 (7)
O2	0.0612 (10)	0.0754 (11)	0.1086 (12)	−0.0262 (9)	0.0020 (8)	−0.0443 (9)
O3	0.0732 (10)	0.0836 (11)	0.0839 (10)	−0.0087 (9)	−0.0127 (8)	−0.0548 (9)
N1	0.0455 (10)	0.0547 (10)	0.0470 (9)	−0.0084 (8)	−0.0074 (8)	−0.0216 (8)
C1	0.0443 (12)	0.0614 (13)	0.0448 (10)	−0.0030 (10)	−0.0130 (9)	−0.0211 (10)
C2	0.0491 (13)	0.0736 (15)	0.0529 (12)	0.0025 (11)	−0.0192 (10)	−0.0271 (11)
C3	0.0546 (14)	0.1005 (19)	0.0614 (13)	0.0044 (14)	−0.0130 (11)	−0.0424 (13)
C4	0.0519 (14)	0.116 (2)	0.0599 (14)	−0.0092 (15)	−0.0056 (11)	−0.0282 (15)
C5	0.0538 (14)	0.0970 (18)	0.0667 (14)	−0.0201 (13)	−0.0109 (12)	−0.0236 (13)
C6	0.0533 (13)	0.0743 (15)	0.0558 (12)	−0.0103 (12)	−0.0134 (10)	−0.0243 (11)
C7	0.0508 (12)	0.0569 (13)	0.0542 (11)	−0.0078 (10)	−0.0138 (10)	−0.0230 (10)
C8	0.0442 (12)	0.0517 (12)	0.0486 (11)	−0.0064 (10)	−0.0102 (9)	−0.0179 (10)
C9	0.0504 (13)	0.0538 (13)	0.0639 (13)	−0.0091 (11)	−0.0088 (10)	−0.0244 (11)
C10	0.0417 (11)	0.0501 (12)	0.0449 (10)	−0.0090 (10)	−0.0112 (9)	−0.0126 (9)
C11	0.0476 (12)	0.0492 (12)	0.0504 (11)	−0.0018 (10)	−0.0184 (9)	−0.0162 (10)
C12	0.0587 (14)	0.0646 (14)	0.0605 (12)	−0.0086 (11)	−0.0091 (10)	−0.0275 (11)
C13	0.0818 (18)	0.0753 (16)	0.0744 (15)	−0.0038 (14)	−0.0150 (13)	−0.0430 (13)
C14	0.100 (2)	0.0622 (15)	0.0858 (17)	0.0001 (15)	−0.0409 (15)	−0.0367 (13)
C15	0.0810 (18)	0.0670 (15)	0.0942 (18)	−0.0148 (13)	−0.0392 (15)	−0.0266 (14)
C16	0.0569 (14)	0.0641 (14)	0.0705 (13)	−0.0072 (11)	−0.0207 (11)	−0.0264 (12)
C17	0.107 (2)	0.0841 (17)	0.0864 (16)	0.0101 (15)	−0.0377 (15)	−0.0545 (15)

Geometric parameters (Å, º) top

O1—C9	1.396 (2)	C11—C16	1.380 (3)
O1—C10	1.378 (2)	C12—C13	1.378 (3)
O2—C9	1.192 (3)	C13—C14	1.361 (5)
O3—C2	1.358 (3)	C14—C15	1.380 (4)
O3—C17	1.431 (3)	C15—C16	1.377 (3)
N1—C8	1.398 (3)	C3—H3	0.9300
N1—C10	1.285 (2)	C4—H4	0.9300
C1—C2	1.409 (3)	C5—H5	0.9300
C1—C6	1.386 (3)	C6—H6	0.9300
C1—C7	1.441 (3)	C7—H7	0.9300
C2—C3	1.383 (3)	C12—H12	0.9300
C3—C4	1.371 (4)	C13—H13	0.9300
C4—C5	1.375 (4)	C14—H14	0.9300
C5—C6	1.376 (3)	C15—H15	0.9300
C7—C8	1.345 (3)	C16—H16	0.9300
C8—C9	1.464 (3)	C17—H17A	0.9600
C10—C11	1.448 (3)	C17—H17B	0.9600
C11—C12	1.385 (3)	C17—H17C	0.9600

O1···N1	2.260 (2)	C4···H17C^vii	3.0100
O2···C14ⁱ	3.236 (3)	C5···H17C^vii	2.9800
O2···C12ⁱⁱ	3.411 (3)	C8···H6	2.8100
O1···H4ⁱⁱⁱ	2.8000	C14···H17A^iv	3.0300
O1···H12	2.4500	C15···H17A^iv	3.0200
O2···H7	2.7000	C16···H4^viii	3.0700
O2···H14ⁱ	2.7800	C17···H3	2.5300
O2···H12ⁱⁱ	2.7900	H3···C17	2.5300
O2···H13ⁱⁱ	2.9200	H3···H17A	2.3700
O3···H7	2.2700	H3···H17C	2.2900
N1···O1	2.260 (2)	H4···O1^ix	2.8000
N1···C6	3.087 (3)	H4···C16^viii	3.0700
N1···H6	2.4300	H4···H16^viii	2.5000
N1···H16	2.6300	H6···N1	2.4300
C1···C10^iv	3.553 (3)	H6···C8	2.8100
C2···C10^iv	3.532 (3)	H7···O2	2.7000
C5···C9^iv	3.481 (4)	H7···O3	2.2700
C6···N1	3.087 (3)	H7···H17B^x	2.5600
C6···C9^iv	3.392 (3)	H12···O1	2.4500
C6···C8^iv	3.561 (3)	H12···O2ⁱⁱ	2.7900
C8···C14^v	3.524 (4)	H13···O2ⁱⁱ	2.9200
C8···C6^iv	3.561 (3)	H14···O2^vi	2.7800
C9···C5^iv	3.481 (4)	H16···N1	2.6300
C9···C6^iv	3.392 (3)	H16···H4^viii	2.5000
C10···C16^v	3.530 (3)	H17A···C3	2.7900
C10···C2^iv	3.532 (3)	H17A···H3	2.3700
C10···C1^iv	3.553 (3)	H17A···C14^iv	3.0300
C12···O2ⁱⁱ	3.411 (3)	H17A···C15^iv	3.0200
C14···C8^v	3.524 (4)	H17B···H7^x	2.5600
C14···O2^vi	3.236 (3)	H17C···C3	2.7400
C16···C10^v	3.530 (3)	H17C···H3	2.2900
C3···H17A	2.7900	H17C···C4^vii	3.0100
C3···H17C	2.7400	H17C···C5^vii	2.9800

C9—O1—C10	105.44 (16)	C14—C15—C16	119.5 (3)
C2—O3—C17	119.06 (18)	C11—C16—C15	120.4 (2)
C8—N1—C10	105.35 (16)	C2—C3—H3	120.00
C2—C1—C6	118.16 (17)	C4—C3—H3	120.00
C2—C1—C7	118.56 (17)	C3—C4—H4	119.00
C6—C1—C7	123.23 (18)	C5—C4—H4	119.00
O3—C2—C1	115.60 (17)	C4—C5—H5	120.00
O3—C2—C3	123.94 (19)	C6—C5—H5	120.00
C1—C2—C3	120.5 (2)	C1—C6—H6	119.00
C2—C3—C4	119.2 (2)	C5—C6—H6	119.00
C3—C4—C5	121.7 (3)	C1—C7—H7	115.00
C4—C5—C6	119.1 (3)	C8—C7—H7	115.00
C1—C6—C5	121.38 (19)	C11—C12—H12	120.00
C1—C7—C8	130.09 (18)	C13—C12—H12	120.00
N1—C8—C7	129.85 (18)	C12—C13—H13	120.00
N1—C8—C9	108.50 (16)	C14—C13—H13	120.00
C7—C8—C9	121.64 (18)	C13—C14—H14	120.00
O1—C9—O2	121.5 (2)	C15—C14—H14	120.00
O1—C9—C8	104.65 (18)	C14—C15—H15	120.00
O2—C9—C8	133.90 (18)	C16—C15—H15	120.00
O1—C10—N1	116.07 (17)	C11—C16—H16	120.00
O1—C10—C11	116.07 (16)	C15—C16—H16	120.00
N1—C10—C11	127.85 (18)	O3—C17—H17A	110.00
C10—C11—C12	121.32 (19)	O3—C17—H17B	109.00
C10—C11—C16	119.45 (17)	O3—C17—H17C	109.00
C12—C11—C16	119.23 (18)	H17A—C17—H17B	109.00
C11—C12—C13	120.2 (2)	H17A—C17—H17C	109.00
C12—C13—C14	120.0 (3)	H17B—C17—H17C	109.00
C13—C14—C15	120.6 (3)

C10—O1—C9—O2	−179.7 (2)	C3—C4—C5—C6	−1.8 (4)
C10—O1—C9—C8	0.43 (19)	C4—C5—C6—C1	0.5 (4)
C9—O1—C10—N1	−0.3 (2)	C1—C7—C8—N1	−2.0 (3)
C9—O1—C10—C11	−179.54 (16)	C1—C7—C8—C9	179.55 (19)
C17—O3—C2—C1	177.88 (19)	N1—C8—C9—O1	−0.5 (2)
C17—O3—C2—C3	−1.9 (3)	N1—C8—C9—O2	179.7 (2)
C10—N1—C8—C7	−178.4 (2)	C7—C8—C9—O1	178.32 (17)
C10—N1—C8—C9	0.3 (2)	C7—C8—C9—O2	−1.5 (4)
C8—N1—C10—O1	0.0 (2)	O1—C10—C11—C12	−2.4 (3)
C8—N1—C10—C11	179.13 (18)	O1—C10—C11—C16	178.04 (17)
C6—C1—C2—O3	178.68 (18)	N1—C10—C11—C12	178.42 (19)
C6—C1—C2—C3	−1.6 (3)	N1—C10—C11—C16	−1.1 (3)
C7—C1—C2—O3	−3.8 (3)	C10—C11—C12—C13	179.2 (2)
C7—C1—C2—C3	175.91 (19)	C16—C11—C12—C13	−1.2 (3)
C2—C1—C6—C5	1.2 (3)	C10—C11—C16—C15	−179.4 (2)
C7—C1—C6—C5	−176.2 (2)	C12—C11—C16—C15	1.1 (3)
C2—C1—C7—C8	−179.85 (19)	C11—C12—C13—C14	0.6 (4)
C6—C1—C7—C8	−2.5 (3)	C12—C13—C14—C15	0.2 (4)
O3—C2—C3—C4	−180.0 (2)	C13—C14—C15—C16	−0.4 (4)
C1—C2—C3—C4	0.3 (3)	C14—C15—C16—C11	−0.3 (4)
C2—C3—C4—C5	1.4 (4)

Symmetry codes: (i) x, y−1, z; (ii) −x, −y+1, −z+1; (iii) x−1, y, z+1; (iv) −x+1, −y+1, −z; (v) −x+1, −y+1, −z+1; (vi) x, y+1, z; (vii) −x+2, −y, −z; (viii) −x+2, −y+1, −z; (ix) x+1, y, z−1; (x) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N1	0.93	2.43	3.087 (3)	127
C17—H17A···Cg3^iv	0.96	2.81	3.682 (3)	151
C17—H17C···Cg2^vii	0.96	2.96	3.832 (3)	151

Symmetry codes: (iv) −x+1, −y+1, −z; (vii) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃NO₃
M_r	279.28
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.8073 (6), 9.6140 (6), 9.8272 (6)
α, β, γ (°)	66.503 (4), 67.248 (4), 71.734 (4)
V (Å³)	691.14 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.08 × 0.05

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14582, 3457, 1464
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.133, 0.93
No. of reflections	3457
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.13

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N1	0.93	2.43	3.087 (3)	127
C17—H17A···Cg3ⁱ	0.96	2.81	3.682 (3)	151
C17—H17C···Cg2ⁱⁱ	0.96	2.96	3.832 (3)	151

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

Acknowledgements

AMA acknowledges the Chemistry Department, Faculty of Science, King Abdul-Aziz University, for providing the laboratories and facilities.

References

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