1-{[(2,3-Dihydro-1H-inden-2-yl)­oxy]meth­yl}quinazoline-2,4(1H,3H)-dione

El-Brollosy, N.R.; Dege, N.; Demirtaş, G.; Attia, M.I.; El-Emam, A.A.; Büyükgüngör, O.

doi:10.1107/S1600536812022350

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1866-o1867

doi:10.1107/S1600536812022350

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1-{[(2,3-Dihydro-1H-inden-2-yl)oxy]methyl}quinazoline-2,4(1H,3H)-dione

Nasser R. El-Brollosy,^a Necmi Dege,^b Güneş Demirtaş,^b ^* Mohamed I. Attia,^a Ali A. El-Emam ^a and Orhan Büyükgüngör ^b

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, 11451 Riyadh, Saudi Arabia, and ^bDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: gunesd@omu.edu.tr

(Received 26 April 2012; accepted 16 May 2012; online 23 May 2012)

In the title molecule, C₁₈H₁₆N₂O₃, the five-membered ring has an envelope conformation, with the substituted C atom deviating by 0.342 (4) Å from the mean plane P calculated for the remainder of the non-H atoms of the 2,3-dihydro-1H-indene fragment. The mean planes of quinazoline-2,4(1H,3H)-dione fragment and P form a dihedral angle of 59.08 (4)°. In the crystal, pairs of N—H⋯O hydrogen bonds link molecules into inversion dimers, and weak C—H⋯O hydrogen bonds and π–π interactions between the benzene rings of the quinazoline ring systems [centroid–centroid distance = 3.538 (3) Å] further consolidate the packing.

Related literature

For the biological activity of quinazoline-2,4(1H,3H)-diones, see: Tran et al. (2004 ); Cao et al. (2010 ) and for the biological activity of non-nucleoside reverse transcriptase inhibitors (NNRTIs), see: Hopkins et al. (1996 , 1999 ); El-Brollosy (2006 , 2007 ); El-Brollosy et al. (2008 , 2009 ). For related structures, see: Liu (2008 ); Karimova et al. (2010 ).

Experimental

Crystal data

C₁₈H₁₆N₂O₃
M_r = 308.33
Triclinic, $[P \overline 1]$
a = 7.6684 (8) Å
b = 10.0717 (10) Å
c = 10.6748 (11) Å
α = 87.199 (8)°
β = 78.332 (8)°
γ = 70.569 (8)°
V = 761.28 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.58 × 0.38 × 0.05 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.948, T_max = 0.995
11601 measured reflections
3156 independent reflections
2078 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.103
S = 1.00
3156 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.86	2.06	2.9106 (18)	169
C9—H9A⋯O2ⁱⁱ	0.97	2.56	3.527 (3)	173
C16—H16⋯O1ⁱⁱⁱ	0.93	2.47	3.378 (2)	166
C10—H10A⋯O3^iv	0.97	2.46	3.404 (2)	165
C5—H5⋯O3^v	0.93	2.47	3.314 (2)	151
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z; (iii) -x+1, -y+1, -z+1; (iv) x+1, y, z; (v) x+1, y+1, z.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: WinGX (Farrugia, 1997 ) and SHELXS97 (Sheldrick, 2008 ); 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 I, global. DOI: 10.1107/S1600536812022350/cv5291sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022350/cv5291Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022350/cv5291Isup3.cml

checkCIF report

Comment top

Non-nucleoside reverse transcriptase inhibitors (NNRTIs) are very promising therapies in the treatment of human immunodeficiency virus (HIV) (Hopkins et al., 1996, 1999). Some series of 3-hydroxyquinazoline-2,4-dione and N-((2-methyl-4(3H)-quinazolinon-6-yl)methyl)dithiocarbamates have been synthesized and evulated for antibacterial activity (Tran et al. 2004; Cao et al. 2010). In continuation to our interest in NNRTIs (El-Brollosy et al. 2006, 2007, 2008, 2009), we synthesized the title compound, (I), as a potential non-nucleoside reverse transcriptase inhibitor.

In (I) (Fig. 1), in the 2,3-dihydro-1H-indene fragment atom C1deviates from the main plane P at 0.342 (4) Å. In the literature, some quinazoline-2,4(1H,3H)-dione structures have been reported (Liu, 2008; Karimova et al. 2010). The C11═O2 and C12═O3 bond lengths are 1.2247 (19) and 1.2144 (18) Å, respectively. The C≐C bond distances range from 1.362 (3) Å to1.394 (2) Å. The torsion angle C1—O1—C10—N1 is -93.88 (17)°.

In the crystal, intermolecular N2—H2···O2 hydrogen bond (Table 1) link two molecules into centrosymmetric dimer. Further, weak C—H···O hydrogen bonds (Table 1) and π–π interactions between the benzene rings of the quinazoline bicycles [centroid-centroid distance = 3.538 (3) Å] consolidate the crystal packing.

Related literature top

For the biological activity of quinazoline-2,4(1H,3H)-diones, see: Tran et al. (2004); Cao et al. (2010) and for the biological activity of non-nucleoside reverse transcriptase inhibitors (NNRTIs), see: Hopkins et al. (1996, 1999); El-Brollosy (2006, 2007); El-Brollosy et al. (2008, 2009). For related structures, see: Liu (2008); Karimova et al. (2010).

Experimental top

Quinazoline-2,4(1H,3H)-dione (162 mg, 1 mmol) was stirred in dry acetonitrile (15 ml) under nitrogen and N,O-bis(trimethylsilyl)acetamide (BSA) (0.87 ml, 3.5 mmol) was added. After a clear solution was obtained (10 min), the mixture was cooled down to -50 °C and TMS trifluoromethanesulfonate (0.18 ml, 1 mmol) was added followed by the dropwise addition of bis(indan-2-yloxy)methane (560 g, 2 mmol). The reaction mixture was stirred at room temperature for 5 h, and quenched by addition of saturated aqueous sodium hydrogen carbonate solution (5 ml). The mixture was evaporated under reduced pressure and the residue was extracted with ether (3 × 50 ml). The combined ether fractions were dried (MgSO₄) and evaporated under reduced pressure. The product was purified on silica gel column chromatography, using 20% ether in petroleum ether (40–60°C), to afford the title compound as a white solid in 71% yield (218 mg). Single crystals were achieved by crystallization from ethanol. M.p. 193–194 ^oC (El-Brollosy, 2007).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: WinGX (Farrugia, 1997) and SHELXS97 (Sheldrick, 2008); 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 (I) showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

1-{[(2,3-Dihydro-1H-inden-2-yl)oxy]methyl}quinazoline- 2,4(1H,3H)-dione top

Crystal data top

C₁₈H₁₆N₂O₃	Z = 2
M_r = 308.33	F(000) = 324
Triclinic, P1	D_x = 1.345 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6684 (8) Å	Cell parameters from 11963 reflections
b = 10.0717 (10) Å	θ = 2.9–27.9°
c = 10.6748 (11) Å	µ = 0.09 mm⁻¹
α = 87.199 (8)°	T = 296 K
β = 78.332 (8)°	Plate, colorless
γ = 70.569 (8)°	0.58 × 0.38 × 0.05 mm
V = 761.28 (13) Å³

Data collection top

Stoe IPDS 2 diffractometer	3156 independent reflections
Radiation source: fine-focus sealed tube	2078 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
rotation method scans	θ_max = 26.5°, θ_min = 2.9°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −9→9
T_min = 0.948, T_max = 0.995	k = −12→12
11601 measured reflections	l = −13→13

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0506P)²] where P = (F_o² + 2F_c²)/3
3156 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₈H₁₆N₂O₃	γ = 70.569 (8)°
M_r = 308.33	V = 761.28 (13) Å³
Triclinic, P1	Z = 2
a = 7.6684 (8) Å	Mo Kα radiation
b = 10.0717 (10) Å	µ = 0.09 mm⁻¹
c = 10.6748 (11) Å	T = 296 K
α = 87.199 (8)°	0.58 × 0.38 × 0.05 mm
β = 78.332 (8)°

Data collection top

Stoe IPDS 2 diffractometer	3156 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2078 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.995	R_int = 0.043
11601 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.00	Δρ_max = 0.15 e Å⁻³
3156 reflections	Δρ_min = −0.16 e Å⁻³
208 parameters

Special details top

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
C1	0.3360 (3)	0.7691 (2)	0.1809 (2)	0.0586 (5)
H1	0.2262	0.7682	0.1477	0.070*
C2	0.2880 (3)	0.8977 (2)	0.2672 (3)	0.0688 (6)
H2A	0.1797	0.9729	0.2480	0.083*
H2B	0.2613	0.8741	0.3566	0.083*
C3	0.4616 (3)	0.94003 (18)	0.23750 (19)	0.0500 (5)
C4	0.5098 (3)	1.0335 (2)	0.3022 (2)	0.0609 (5)
H4	0.4299	1.0798	0.3760	0.073*
C5	0.6771 (3)	1.0575 (2)	0.2565 (3)	0.0705 (6)
H5	0.7098	1.1214	0.2990	0.085*
C6	0.7955 (3)	0.9884 (3)	0.1493 (3)	0.0755 (7)
H6	0.9087	1.0055	0.1198	0.091*
C7	0.7506 (3)	0.8938 (2)	0.0837 (2)	0.0715 (6)
H7	0.8329	0.8462	0.0112	0.086*
C8	0.5807 (3)	0.87095 (18)	0.12792 (19)	0.0529 (5)
C9	0.4947 (3)	0.7796 (2)	0.07299 (19)	0.0657 (6)
H9A	0.5867	0.6874	0.0489	0.079*
H9B	0.4456	0.8222	−0.0017	0.079*
C10	0.4294 (2)	0.51886 (17)	0.19832 (17)	0.0416 (4)
H10A	0.5368	0.4475	0.2233	0.050*
H10B	0.4588	0.5283	0.1063	0.050*
C11	0.1516 (2)	0.48967 (16)	0.14342 (15)	0.0366 (4)
C12	−0.0368 (2)	0.36456 (17)	0.28236 (17)	0.0422 (4)
C13	0.0822 (2)	0.35258 (16)	0.37605 (15)	0.0379 (4)
C14	0.0470 (3)	0.28777 (19)	0.49221 (17)	0.0495 (4)
H14	−0.0524	0.2519	0.5098	0.059*
C15	0.1577 (3)	0.27652 (19)	0.58079 (18)	0.0548 (5)
H15	0.1350	0.2321	0.6579	0.066*
C16	0.3030 (3)	0.33168 (19)	0.55437 (17)	0.0515 (5)
H16	0.3775	0.3247	0.6148	0.062*
C17	0.3401 (2)	0.39664 (18)	0.44111 (16)	0.0446 (4)
H17	0.4386	0.4335	0.4253	0.053*
C18	0.2296 (2)	0.40725 (16)	0.34981 (15)	0.0350 (4)
N1	0.26417 (18)	0.47265 (13)	0.23194 (12)	0.0356 (3)
N2	0.00901 (19)	0.43362 (14)	0.17284 (13)	0.0422 (3)
H2	−0.0598	0.4425	0.1165	0.051*
O1	0.40148 (17)	0.64742 (12)	0.25756 (11)	0.0487 (3)
O2	0.17725 (17)	0.54975 (13)	0.04228 (11)	0.0490 (3)
O3	−0.16859 (19)	0.32033 (15)	0.29619 (14)	0.0658 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0577 (12)	0.0473 (10)	0.0821 (15)	−0.0195 (9)	−0.0355 (11)	0.0023 (10)
C2	0.0494 (11)	0.0560 (12)	0.1013 (18)	−0.0166 (10)	−0.0134 (11)	−0.0133 (11)
C3	0.0489 (10)	0.0378 (9)	0.0665 (13)	−0.0140 (8)	−0.0192 (9)	0.0032 (9)
C4	0.0620 (12)	0.0467 (11)	0.0785 (15)	−0.0201 (9)	−0.0190 (11)	−0.0048 (10)
C5	0.0794 (16)	0.0567 (12)	0.0951 (18)	−0.0362 (12)	−0.0405 (14)	0.0135 (12)
C6	0.0627 (14)	0.0710 (15)	0.102 (2)	−0.0354 (12)	−0.0199 (14)	0.0302 (14)
C7	0.0780 (15)	0.0614 (13)	0.0697 (15)	−0.0267 (12)	−0.0002 (12)	0.0189 (11)
C8	0.0673 (13)	0.0396 (9)	0.0538 (11)	−0.0183 (9)	−0.0182 (10)	0.0129 (8)
C9	0.1052 (17)	0.0496 (11)	0.0515 (12)	−0.0336 (11)	−0.0238 (12)	0.0084 (9)
C10	0.0373 (9)	0.0488 (10)	0.0457 (10)	−0.0207 (8)	−0.0123 (7)	0.0004 (8)
C11	0.0381 (9)	0.0392 (8)	0.0378 (9)	−0.0160 (7)	−0.0143 (7)	0.0012 (7)
C12	0.0386 (9)	0.0445 (9)	0.0524 (11)	−0.0217 (8)	−0.0161 (8)	0.0050 (8)
C13	0.0387 (9)	0.0364 (8)	0.0409 (9)	−0.0130 (7)	−0.0121 (7)	0.0020 (7)
C14	0.0491 (11)	0.0502 (10)	0.0512 (11)	−0.0204 (9)	−0.0100 (9)	0.0125 (8)
C15	0.0673 (13)	0.0505 (11)	0.0427 (11)	−0.0132 (10)	−0.0155 (9)	0.0126 (8)
C16	0.0619 (12)	0.0492 (10)	0.0451 (10)	−0.0112 (9)	−0.0272 (9)	0.0035 (8)
C17	0.0461 (10)	0.0461 (10)	0.0478 (10)	−0.0165 (8)	−0.0218 (8)	0.0029 (8)
C18	0.0375 (9)	0.0334 (8)	0.0364 (9)	−0.0109 (7)	−0.0139 (7)	0.0002 (6)
N1	0.0368 (7)	0.0413 (7)	0.0367 (7)	−0.0192 (6)	−0.0152 (6)	0.0041 (6)
N2	0.0429 (8)	0.0546 (8)	0.0423 (8)	−0.0257 (7)	−0.0232 (6)	0.0079 (7)
O1	0.0582 (8)	0.0530 (7)	0.0509 (7)	−0.0340 (6)	−0.0203 (6)	0.0023 (6)
O2	0.0567 (8)	0.0639 (8)	0.0401 (7)	−0.0323 (6)	−0.0222 (6)	0.0146 (6)
O3	0.0605 (8)	0.0829 (10)	0.0790 (10)	−0.0490 (8)	−0.0326 (7)	0.0265 (8)

Geometric parameters (Å, º) top

C1—O1	1.443 (2)	C10—N1	1.4641 (19)
C1—C9	1.525 (3)	C10—H10A	0.9700
C1—C2	1.525 (3)	C10—H10B	0.9700
C1—H1	0.9800	C11—O2	1.2247 (19)
C2—C3	1.499 (3)	C11—N2	1.3663 (19)
C2—H2A	0.9700	C11—N1	1.3725 (19)
C2—H2B	0.9700	C12—O3	1.2144 (18)
C3—C4	1.378 (3)	C12—N2	1.375 (2)
C3—C8	1.382 (3)	C12—C13	1.460 (2)
C4—C5	1.372 (3)	C13—C18	1.389 (2)
C4—H4	0.9300	C13—C14	1.393 (2)
C5—C6	1.362 (3)	C14—C15	1.370 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.377 (3)	C15—C16	1.378 (3)
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.383 (3)	C16—C17	1.371 (2)
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.495 (3)	C17—C18	1.394 (2)
C9—H9A	0.9700	C17—H17	0.9300
C9—H9B	0.9700	C18—N1	1.410 (2)
C10—O1	1.4011 (19)	N2—H2	0.8600

O1—C1—C9	110.81 (16)	O1—C10—H10A	109.1
O1—C1—C2	106.40 (17)	N1—C10—H10A	109.1
C9—C1—C2	105.33 (16)	O1—C10—H10B	109.1
O1—C1—H1	111.3	N1—C10—H10B	109.1
C9—C1—H1	111.3	H10A—C10—H10B	107.8
C2—C1—H1	111.3	O2—C11—N2	121.04 (15)
C3—C2—C1	104.25 (17)	O2—C11—N1	122.58 (14)
C3—C2—H2A	110.9	N2—C11—N1	116.37 (14)
C1—C2—H2A	110.9	O3—C12—N2	120.33 (16)
C3—C2—H2B	110.9	O3—C12—C13	124.94 (16)
C1—C2—H2B	110.9	N2—C12—C13	114.72 (13)
H2A—C2—H2B	108.9	C18—C13—C14	119.96 (16)
C4—C3—C8	120.32 (18)	C18—C13—C12	119.93 (15)
C4—C3—C2	129.21 (19)	C14—C13—C12	120.11 (15)
C8—C3—C2	110.47 (17)	C15—C14—C13	120.45 (17)
C5—C4—C3	119.3 (2)	C15—C14—H14	119.8
C5—C4—H4	120.4	C13—C14—H14	119.8
C3—C4—H4	120.4	C14—C15—C16	119.26 (17)
C6—C5—C4	120.5 (2)	C14—C15—H15	120.4
C6—C5—H5	119.8	C16—C15—H15	120.4
C4—C5—H5	119.8	C17—C16—C15	121.49 (18)
C5—C6—C7	121.1 (2)	C17—C16—H16	119.3
C5—C6—H6	119.4	C15—C16—H16	119.3
C7—C6—H6	119.4	C16—C17—C18	119.68 (16)
C6—C7—C8	118.7 (2)	C16—C17—H17	120.2
C6—C7—H7	120.6	C18—C17—H17	120.2
C8—C7—H7	120.6	C13—C18—C17	119.16 (15)
C3—C8—C7	120.04 (19)	C13—C18—N1	119.53 (14)
C3—C8—C9	110.30 (17)	C17—C18—N1	121.31 (14)
C7—C8—C9	129.6 (2)	C11—N1—C18	122.06 (13)
C8—C9—C1	104.28 (16)	C11—N1—C10	117.92 (13)
C8—C9—H9A	110.9	C18—N1—C10	119.96 (13)
C1—C9—H9A	110.9	C11—N2—C12	127.31 (14)
C8—C9—H9B	110.9	C11—N2—H2	116.3
C1—C9—H9B	110.9	C12—N2—H2	116.3
H9A—C9—H9B	108.9	C10—O1—C1	114.24 (13)
O1—C10—N1	112.53 (13)

O1—C1—C2—C3	96.00 (19)	C14—C15—C16—C17	−0.5 (3)
C9—C1—C2—C3	−21.7 (2)	C15—C16—C17—C18	−0.2 (3)
C1—C2—C3—C4	−167.6 (2)	C14—C13—C18—C17	−0.2 (2)
C1—C2—C3—C8	12.9 (2)	C12—C13—C18—C17	179.10 (15)
C8—C3—C4—C5	0.2 (3)	C14—C13—C18—N1	180.00 (15)
C2—C3—C4—C5	−179.3 (2)	C12—C13—C18—N1	−0.7 (2)
C3—C4—C5—C6	−0.9 (3)	C16—C17—C18—C13	0.6 (2)
C4—C5—C6—C7	0.4 (3)	C16—C17—C18—N1	−179.66 (15)
C5—C6—C7—C8	0.8 (3)	O2—C11—N1—C18	177.94 (15)
C4—C3—C8—C7	1.0 (3)	N2—C11—N1—C18	−3.1 (2)
C2—C3—C8—C7	−179.43 (19)	O2—C11—N1—C10	−4.9 (2)
C4—C3—C8—C9	−178.03 (17)	N2—C11—N1—C10	174.07 (14)
C2—C3—C8—C9	1.6 (2)	C13—C18—N1—C11	2.8 (2)
C6—C7—C8—C3	−1.4 (3)	C17—C18—N1—C11	−176.99 (15)
C6—C7—C8—C9	177.3 (2)	C13—C18—N1—C10	−174.32 (14)
C3—C8—C9—C1	−15.3 (2)	C17—C18—N1—C10	5.9 (2)
C7—C8—C9—C1	165.8 (2)	O1—C10—N1—C11	103.02 (16)
O1—C1—C9—C8	−92.08 (18)	O1—C10—N1—C18	−79.75 (18)
C2—C1—C9—C8	22.6 (2)	O2—C11—N2—C12	−179.57 (16)
O3—C12—C13—C18	179.98 (17)	N1—C11—N2—C12	1.4 (2)
N2—C12—C13—C18	−0.9 (2)	O3—C12—N2—C11	179.69 (17)
O3—C12—C13—C14	−0.7 (3)	C13—C12—N2—C11	0.5 (2)
N2—C12—C13—C14	178.46 (16)	N1—C10—O1—C1	−93.88 (17)
C18—C13—C14—C15	−0.5 (3)	C9—C1—O1—C10	−73.73 (18)
C12—C13—C14—C15	−179.80 (17)	C2—C1—O1—C10	172.28 (14)
C13—C14—C15—C16	0.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	2.06	2.9106 (18)	169
C9—H9A···O2ⁱⁱ	0.97	2.56	3.527 (3)	173
C16—H16···O1ⁱⁱⁱ	0.93	2.47	3.378 (2)	166
C10—H10A···O3^iv	0.97	2.46	3.404 (2)	165
C5—H5···O3^v	0.93	2.47	3.314 (2)	151

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂O₃
M_r	308.33
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.6684 (8), 10.0717 (10), 10.6748 (11)
α, β, γ (°)	87.199 (8), 78.332 (8), 70.569 (8)
V (Å³)	761.28 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.58 × 0.38 × 0.05

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.948, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	11601, 3156, 2078
R_int	0.043

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.103, 1.00
No. of reflections	3156
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), WinGX (Farrugia, 1997) and SHELXS97 (Sheldrick, 2008), 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
N2—H2···O2ⁱ	0.86	2.06	2.9106 (18)	169.2
C9—H9A···O2ⁱⁱ	0.97	2.56	3.527 (3)	173.1
C16—H16···O1ⁱⁱⁱ	0.93	2.47	3.378 (2)	165.5
C10—H10A···O3^iv	0.97	2.46	3.404 (2)	165.1
C5—H5···O3^v	0.93	2.47	3.314 (2)	150.7

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

Acknowledgements

The authors thank the Ondokuz Mayıs University Research Fund for financial support. The financial support of the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, is greatly appreciated.

References

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