3-Isopropyl-2-(4-methoxy­phen­oxy)-1-benzo­furo[3,2-d]pyrimidin-4(3H)-one

Chen, X.-B.; Xu, J.; Zheng, A.-H.; Tian, J.-H.; Luo, H.

doi:10.1107/S1600536809042925

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2839

https://doi.org/10.1107/S1600536809042925

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3-Isopropyl-2-(4-methoxyphenoxy)-1-benzofuro[3,2-d]pyrimidin-4(3H)-one

Xiao-Bao Chen,^a ^* Jing Xu,^a Ai-Hua Zheng,^a Jia-Hua Tian ^a and Hong Luo ^a

^aInstitute of Medicinal Chemistry, Yunyang Medical College, Shiyan, Hubei 442000, People's Republic of China
^*Correspondence e-mail: chenxiaobao@yahoo.com.cn

(Received 18 October 2009; accepted 19 October 2009; online 23 October 2009)

In the title compound, C₂₀H₁₈N₂O₄, all non-H atoms of the three fused rings of the benzofuro[3,2-d]pyrimidine system are almost coplanar (r.m.s. deviation 0.021 Å). The dihedral angle between the fused ring system and the benzene ring is 1.47 (12)°. Intramolecular and intermolecular C—H⋯O hydrogen bonds together with weak C—H⋯π interactions stabilize the structure.

Related literature

For the biological activity of benzofuropyrimidine derivatives, see: Bodke & Sangapure (2003 ). For the synthesis of the title compound, see: Ding et al. (2004 ). For the structures of other fused pyrimidinone derivatives, see: Hu et al. (2005 , 2006 , 2007 ).

Experimental

Crystal data

C₂₀H₁₈N₂O₄
M_r = 350.36
Monoclinic, P 2₁ /c
a = 10.0358 (7) Å
b = 14.2879 (10) Å
c = 13.2071 (9) Å
β = 112.089 (1)°
V = 1754.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.26 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
11156 measured reflections
3809 independent reflections
3354 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.155
S = 1.22
3809 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.19 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
C4—H4⋯O4ⁱ	0.93	2.49	3.311 (3)	147
C11—H11⋯O2	0.98	2.25	2.761 (3)	111
C12—H12C⋯O3	0.96	2.32	2.845 (4)	114
C13—H13A⋯O3	0.96	2.41	2.957 (3)	116
C16—H16⋯Cg2ⁱⁱ	0.93	2.76	3.551 (2)	143
C19—H19⋯Cg3ⁱⁱⁱ	0.93	2.90	3.742 (3)	152
Symmetry codes: (i) -x+2, -y+1, -z; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg2 and Cg3 are the centroids of the N1/C8/C7/C10/N2/C9 and C1–C6 rings, respectively.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809042925/bt5104sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042925/bt5104Isup2.hkl

checkCIF report

Comment top

Benzofuropyrimidine derivatives are of interest as possible antiviral agents, and because of their other biological properties, including antibacterial, antifungal, antiallergic and antiinflammatory activities (Bodke & Sangapure, 2003). We have recently focused on the synthesis of the fused heterocyclic systems containing pyrimidinone via aza-Wittig reactions at room temperature (Ding et al., 2004). We present here the structure of such a benzofuropyrimidinone derivative. Fig. 1 shows the molecular structure of the title compound with the atomic numbering scheme. Intramolecular C—H···O and intermolecular C—H···O hydrogen bonds together with weak C—H···π interactions (Table 1) stabilize the structure. (Fig.2).

Related literature top

For the biological activity of benzofuropyrimidine derivatives, see: Bodke & Sangapure (2003). For the synthesis of the title compound, see: Ding et al. (2004). For the structures of other fused pyrimidinone derivatives, see: Hu et al. (2005, 2006, 2007). Cg2 and Cg3 are the centroids of

the N1/C8/C7/C10/N2/C9 and C1–C6 rings, respectively.

Experimental top

To a solution of N-(2-ethoxycarbonylbenzofuran-3-yl)iminotriphenylphosphorane (3 mmol) in dry dichloromethane (15 ml) was added isopropyl isocyanate (3 mmol) under nitrogen at room temperature. After the reaction mixture had been allowed to stand for 20 h at 273–278 K, the solvent was removed under reduced pressure and diethyl ether-petroleum ether (1:2 v/v, 20 ml) was added to precipitate the triphenylphosphine oxide. After filtration, the solvent was removed to give the ethyl 3-((isopropylimino)methyleneamino)-2,3-dihydrobenzofuran-2-carboxylate, which was used directly without further purification. To a solution of ethyl 3-((isopropylimino)methyleneamino)-2,3- dihydrobenzofuran-2-carboxylate in acetonitrile (15 ml) were added 4-methylphenol (3 mmol) and anhydrous K₂CO₃ (1 mmol). The mixture was stirred for 6 h at 313–323 K. The solution was concentrated under reduced pressure and the residue was recrystallized from dichloromethane and ethanol (1:2 v/v) to give the title compound. Suitable crystals were obtained by vapour diffusion of ethanol into dichloromethane at room temperature.

Structure description top

For the biological activity of benzofuropyrimidine derivatives, see: Bodke & Sangapure (2003). For the synthesis of the title compound, see: Ding et al. (2004). For the structures of other fused pyrimidinone derivatives, see: Hu et al. (2005, 2006, 2007). Cg2 and Cg3 are the centroids of

the N1/C8/C7/C10/N2/C9 and C1–C6 rings, respectively.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT(Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecular structure of (I), showing the atom labelling schemeand with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A partial view of the crystal packing of (I), showing the formation of C—H···O hydrogen-bonded. showing as dashed lines.

3-Isopropyl-2-(4-methoxyphenoxy)-1-benzofuro[3,2-d]pyrimidin- 4(3H)-one top

Crystal data top

C₂₀H₁₈N₂O₄	F(000) = 736
M_r = 350.36	D_x = 1.326 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.0358 (7) Å	Cell parameters from 4035 reflections
b = 14.2879 (10) Å	θ = 2.2–27.2°
c = 13.2071 (9) Å	µ = 0.09 mm⁻¹
β = 112.089 (1)°	T = 298 K
V = 1754.8 (2) Å³	Block, colorless
Z = 4	0.26 × 0.13 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3354 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.040
Graphite monochromator	θ_max = 27.0°, θ_min = 2.2°
phi and ω scans	h = −12→12
11156 measured reflections	k = −14→18
3809 independent reflections	l = −16→16

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 1.22	w = 1/[σ²(F_o²) + (0.0482P)² + 0.6117P] where P = (F_o² + 2F_c²)/3
3809 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₁₈N₂O₄	V = 1754.8 (2) Å³
M_r = 350.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0358 (7) Å	µ = 0.09 mm⁻¹
b = 14.2879 (10) Å	T = 298 K
c = 13.2071 (9) Å	0.26 × 0.13 × 0.10 mm
β = 112.089 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3354 reflections with I > 2σ(I)
11156 measured reflections	R_int = 0.040
3809 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.22	Δρ_max = 0.19 e Å⁻³
3809 reflections	Δρ_min = −0.23 e Å⁻³
238 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	0.7439 (2)	0.49152 (15)	0.08888 (16)	0.0449 (5)
C2	0.8316 (3)	0.53714 (18)	0.04468 (19)	0.0556 (6)
H2	0.8998	0.5043	0.0268	0.067*
C3	0.8149 (3)	0.63207 (19)	0.0280 (2)	0.0665 (7)
H3	0.8725	0.6640	−0.0016	0.080*
C4	0.7126 (3)	0.68112 (18)	0.0549 (2)	0.0649 (7)
H4	0.7023	0.7451	0.0413	0.078*
C5	0.6270 (3)	0.63811 (17)	0.1005 (2)	0.0588 (6)
H5	0.5600	0.6713	0.1194	0.071*
C6	0.6450 (2)	0.54273 (16)	0.11700 (17)	0.0484 (5)
C7	0.6210 (2)	0.39759 (16)	0.15826 (17)	0.0453 (5)
C8	0.7248 (2)	0.39635 (15)	0.11576 (16)	0.0428 (5)
C9	0.7502 (2)	0.24186 (15)	0.13723 (17)	0.0440 (5)
C10	0.5734 (2)	0.31676 (17)	0.19732 (17)	0.0480 (5)
C11	0.6003 (2)	0.14330 (17)	0.21223 (19)	0.0523 (6)
H11	0.5180	0.1570	0.2325	0.063*
C12	0.5457 (3)	0.0739 (2)	0.1184 (2)	0.0671 (7)
H12A	0.4782	0.1044	0.0552	0.101*
H12B	0.4994	0.0226	0.1389	0.101*
H12C	0.6251	0.0508	0.1019	0.101*
C13	0.7157 (3)	0.10533 (19)	0.3141 (2)	0.0654 (7)
H13A	0.8000	0.0910	0.2992	0.098*
H13B	0.6815	0.0495	0.3369	0.098*
H13C	0.7390	0.1513	0.3712	0.098*
C14	0.9024 (2)	0.14978 (15)	0.07749 (18)	0.0448 (5)
C15	0.8475 (2)	0.14131 (19)	−0.0328 (2)	0.0605 (6)
H15	0.7490	0.1470	−0.0714	0.073*
C16	0.9378 (2)	0.12422 (18)	−0.08780 (19)	0.0567 (6)
H16	0.9002	0.1187	−0.1635	0.068*
C17	1.0832 (2)	0.11536 (14)	−0.03082 (18)	0.0438 (5)
C18	1.1364 (2)	0.12380 (19)	0.08137 (19)	0.0601 (6)
H18	1.2347	0.1177	0.1207	0.072*
C19	1.0466 (2)	0.14111 (19)	0.13570 (19)	0.0574 (6)
H19	1.0834	0.1469	0.2114	0.069*
C20	1.1334 (3)	0.1004 (2)	−0.1929 (2)	0.0735 (8)
H20A	1.0674	0.0498	−0.2234	0.110*
H20B	1.2143	0.0941	−0.2144	0.110*
H20C	1.0859	0.1589	−0.2192	0.110*
N1	0.79382 (18)	0.31642 (13)	0.10474 (14)	0.0452 (4)
N2	0.64378 (18)	0.23540 (13)	0.17913 (14)	0.0456 (4)
O1	0.56950 (16)	0.48638 (11)	0.16127 (13)	0.0528 (4)
O2	0.48616 (19)	0.31249 (13)	0.24071 (16)	0.0677 (5)
O3	0.80979 (17)	0.15842 (11)	0.13495 (14)	0.0561 (4)
O4	1.18117 (17)	0.09783 (12)	−0.07769 (13)	0.0584 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0430 (11)	0.0496 (12)	0.0382 (11)	−0.0016 (9)	0.0107 (9)	−0.0053 (9)
C2	0.0547 (13)	0.0561 (15)	0.0600 (14)	−0.0039 (11)	0.0262 (11)	−0.0047 (11)
C3	0.0730 (17)	0.0602 (16)	0.0691 (17)	−0.0135 (13)	0.0298 (14)	−0.0014 (13)
C4	0.0740 (17)	0.0493 (14)	0.0637 (16)	−0.0016 (12)	0.0171 (13)	−0.0009 (12)
C5	0.0604 (14)	0.0517 (14)	0.0591 (15)	0.0087 (11)	0.0165 (12)	−0.0055 (11)
C6	0.0458 (11)	0.0535 (13)	0.0413 (11)	0.0041 (10)	0.0112 (9)	−0.0028 (9)
C7	0.0404 (11)	0.0526 (13)	0.0428 (11)	0.0062 (9)	0.0154 (9)	−0.0020 (9)
C8	0.0387 (10)	0.0508 (12)	0.0369 (10)	0.0011 (9)	0.0121 (8)	−0.0028 (9)
C9	0.0417 (11)	0.0494 (12)	0.0416 (11)	0.0044 (9)	0.0165 (9)	0.0009 (9)
C10	0.0412 (11)	0.0598 (14)	0.0440 (12)	0.0039 (10)	0.0172 (9)	−0.0007 (10)
C11	0.0488 (12)	0.0560 (14)	0.0592 (14)	−0.0052 (10)	0.0283 (11)	0.0011 (11)
C12	0.0556 (14)	0.0657 (16)	0.0727 (17)	−0.0083 (12)	0.0159 (13)	−0.0067 (13)
C13	0.0754 (17)	0.0685 (17)	0.0530 (14)	−0.0054 (13)	0.0250 (13)	0.0105 (12)
C14	0.0465 (11)	0.0387 (11)	0.0533 (13)	0.0051 (9)	0.0236 (10)	0.0039 (9)
C15	0.0395 (11)	0.0805 (18)	0.0561 (15)	0.0139 (11)	0.0118 (10)	0.0019 (12)
C16	0.0485 (12)	0.0753 (17)	0.0423 (12)	0.0080 (11)	0.0126 (10)	−0.0022 (11)
C17	0.0438 (11)	0.0368 (11)	0.0532 (12)	0.0047 (8)	0.0210 (9)	0.0034 (9)
C18	0.0355 (11)	0.0880 (19)	0.0519 (14)	0.0053 (11)	0.0109 (10)	0.0042 (12)
C19	0.0516 (13)	0.0754 (17)	0.0435 (12)	0.0023 (12)	0.0158 (10)	0.0002 (11)
C20	0.0799 (18)	0.088 (2)	0.0628 (17)	0.0156 (15)	0.0391 (15)	−0.0024 (14)
N1	0.0425 (9)	0.0485 (10)	0.0489 (10)	0.0028 (8)	0.0220 (8)	−0.0005 (8)
N2	0.0415 (9)	0.0539 (11)	0.0432 (10)	−0.0009 (8)	0.0179 (8)	0.0001 (8)
O1	0.0511 (9)	0.0542 (9)	0.0589 (10)	0.0086 (7)	0.0272 (8)	−0.0022 (7)
O2	0.0671 (11)	0.0722 (12)	0.0841 (12)	0.0062 (9)	0.0517 (10)	0.0032 (9)
O3	0.0616 (10)	0.0494 (9)	0.0714 (11)	0.0106 (7)	0.0411 (8)	0.0114 (8)
O4	0.0529 (9)	0.0666 (11)	0.0617 (10)	0.0120 (8)	0.0285 (8)	0.0043 (8)

Geometric parameters (Å, º) top

C1—C2	1.388 (3)	C11—H11	0.9800
C1—C6	1.392 (3)	C12—H12A	0.9600
C1—C8	1.436 (3)	C12—H12B	0.9600
C2—C3	1.374 (4)	C12—H12C	0.9600
C2—H2	0.9300	C13—H13A	0.9600
C3—C4	1.395 (4)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.367 (4)	C14—C15	1.355 (3)
C4—H4	0.9300	C14—C19	1.365 (3)
C5—C6	1.381 (3)	C14—O3	1.409 (2)
C5—H5	0.9300	C15—C16	1.380 (3)
C6—O1	1.377 (3)	C15—H15	0.9300
C7—C8	1.357 (3)	C16—C17	1.373 (3)
C7—O1	1.376 (3)	C16—H16	0.9300
C7—C10	1.418 (3)	C17—O4	1.368 (2)
C8—N1	1.372 (3)	C17—C18	1.378 (3)
C9—N1	1.285 (3)	C18—C19	1.369 (3)
C9—O3	1.339 (3)	C18—H18	0.9300
C9—N2	1.378 (3)	C19—H19	0.9300
C10—O2	1.215 (3)	C20—O4	1.414 (3)
C10—N2	1.427 (3)	C20—H20A	0.9600
C11—N2	1.502 (3)	C20—H20B	0.9600
C11—C13	1.508 (3)	C20—H20C	0.9600
C11—C12	1.519 (3)

C2—C1—C6	119.6 (2)	H12A—C12—H12C	109.5
C2—C1—C8	135.5 (2)	H12B—C12—H12C	109.5
C6—C1—C8	104.85 (19)	C11—C13—H13A	109.5
C3—C2—C1	118.2 (2)	C11—C13—H13B	109.5
C3—C2—H2	120.9	H13A—C13—H13B	109.5
C1—C2—H2	120.9	C11—C13—H13C	109.5
C2—C3—C4	120.8 (2)	H13A—C13—H13C	109.5
C2—C3—H3	119.6	H13B—C13—H13C	109.5
C4—C3—H3	119.6	C15—C14—C19	120.9 (2)
C5—C4—C3	122.1 (2)	C15—C14—O3	120.16 (19)
C5—C4—H4	119.0	C19—C14—O3	118.6 (2)
C3—C4—H4	119.0	C14—C15—C16	120.0 (2)
C4—C5—C6	116.5 (2)	C14—C15—H15	120.0
C4—C5—H5	121.7	C16—C15—H15	120.0
C6—C5—H5	121.7	C17—C16—C15	120.0 (2)
O1—C6—C5	125.7 (2)	C17—C16—H16	120.0
O1—C6—C1	111.57 (19)	C15—C16—H16	120.0
C5—C6—C1	122.7 (2)	O4—C17—C16	124.4 (2)
C8—C7—O1	112.26 (19)	O4—C17—C18	116.66 (19)
C8—C7—C10	123.7 (2)	C16—C17—C18	118.9 (2)
O1—C7—C10	123.99 (18)	C19—C18—C17	120.9 (2)
C7—C8—N1	123.5 (2)	C19—C18—H18	119.5
C7—C8—C1	106.56 (19)	C17—C18—H18	119.5
N1—C8—C1	129.93 (18)	C14—C19—C18	119.2 (2)
N1—C9—O3	121.27 (18)	C14—C19—H19	120.4
N1—C9—N2	127.03 (19)	C18—C19—H19	120.4
O3—C9—N2	111.69 (18)	O4—C20—H20A	109.5
O2—C10—C7	127.8 (2)	O4—C20—H20B	109.5
O2—C10—N2	121.9 (2)	H20A—C20—H20B	109.5
C7—C10—N2	110.30 (17)	O4—C20—H20C	109.5
N2—C11—C13	111.44 (18)	H20A—C20—H20C	109.5
N2—C11—C12	112.94 (19)	H20B—C20—H20C	109.5
C13—C11—C12	114.4 (2)	C9—N1—C8	113.92 (17)
N2—C11—H11	105.7	C9—N2—C10	121.34 (18)
C13—C11—H11	105.7	C9—N2—C11	121.94 (18)
C12—C11—H11	105.7	C10—N2—C11	116.67 (17)
C11—C12—H12A	109.5	C7—O1—C6	104.74 (16)
C11—C12—H12B	109.5	C9—O3—C14	118.74 (16)
H12A—C12—H12B	109.5	C17—O4—C20	118.16 (19)
C11—C12—H12C	109.5

C6—C1—C2—C3	−1.4 (3)	C15—C14—C19—C18	0.1 (4)
C8—C1—C2—C3	178.1 (2)	O3—C14—C19—C18	173.9 (2)
C1—C2—C3—C4	0.0 (4)	C17—C18—C19—C14	0.2 (4)
C2—C3—C4—C5	1.3 (4)	O3—C9—N1—C8	−177.98 (18)
C3—C4—C5—C6	−1.1 (4)	N2—C9—N1—C8	0.8 (3)
C4—C5—C6—O1	−179.7 (2)	C7—C8—N1—C9	0.8 (3)
C4—C5—C6—C1	−0.3 (3)	C1—C8—N1—C9	179.9 (2)
C2—C1—C6—O1	−178.92 (19)	N1—C9—N2—C10	−3.9 (3)
C8—C1—C6—O1	1.4 (2)	O3—C9—N2—C10	174.94 (17)
C2—C1—C6—C5	1.6 (3)	N1—C9—N2—C11	178.7 (2)
C8—C1—C6—C5	−178.1 (2)	O3—C9—N2—C11	−2.5 (3)
O1—C7—C8—N1	179.51 (18)	O2—C10—N2—C9	−175.2 (2)
C10—C7—C8—N1	0.8 (3)	C7—C10—N2—C9	4.8 (3)
O1—C7—C8—C1	0.2 (2)	O2—C10—N2—C11	2.4 (3)
C10—C7—C8—C1	−178.48 (19)	C7—C10—N2—C11	−177.66 (17)
C2—C1—C8—C7	179.5 (2)	C13—C11—N2—C9	70.7 (3)
C6—C1—C8—C7	−1.0 (2)	C12—C11—N2—C9	−59.8 (3)
C2—C1—C8—N1	0.2 (4)	C13—C11—N2—C10	−106.9 (2)
C6—C1—C8—N1	179.8 (2)	C12—C11—N2—C10	122.7 (2)
C8—C7—C10—O2	176.5 (2)	C8—C7—O1—C6	0.7 (2)
O1—C7—C10—O2	−2.0 (4)	C10—C7—O1—C6	179.3 (2)
C8—C7—C10—N2	−3.5 (3)	C5—C6—O1—C7	178.2 (2)
O1—C7—C10—N2	177.99 (18)	C1—C6—O1—C7	−1.3 (2)
C19—C14—C15—C16	−0.4 (4)	N1—C9—O3—C14	−11.9 (3)
O3—C14—C15—C16	−174.0 (2)	N2—C9—O3—C14	169.19 (17)
C14—C15—C16—C17	0.3 (4)	C15—C14—O3—C9	−79.2 (3)
C15—C16—C17—O4	179.5 (2)	C19—C14—O3—C9	107.1 (2)
C15—C16—C17—C18	0.0 (4)	C16—C17—O4—C20	8.2 (3)
O4—C17—C18—C19	−179.8 (2)	C18—C17—O4—C20	−172.2 (2)
C16—C17—C18—C19	−0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O4ⁱ	0.93	2.49	3.311 (3)	147
C11—H11···O2	0.98	2.25	2.761 (3)	111
C12—H12C···O3	0.96	2.32	2.845 (4)	114
C13—H13A···O3	0.96	2.41	2.957 (3)	116
C16—H16···Cg2ⁱⁱ	0.93	2.76	3.551 (2)	143
C19—H19···Cg3ⁱⁱⁱ	0.93	2.90	3.742 (3)	152

Symmetry codes: (i) −x+2, −y+1, −z; (ii) x, −y−1/2, z−3/2; (iii) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₂O₄
M_r	350.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.0358 (7), 14.2879 (10), 13.2071 (9)
β (°)	112.089 (1)
V (Å³)	1754.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.26 × 0.13 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11156, 3809, 3354
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.155, 1.22
No. of reflections	3809
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.23

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT(Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O4ⁱ	0.93	2.49	3.311 (3)	146.9
C11—H11···O2	0.98	2.25	2.761 (3)	111
C12—H12C···O3	0.96	2.32	2.845 (4)	114
C13—H13A···O3	0.96	2.41	2.957 (3)	116
C16—H16···Cg2ⁱⁱ	0.93	2.76	3.551 (2)	143
C19—H19···Cg3ⁱⁱⁱ	0.93	2.90	3.742 (3)	152

Symmetry codes: (i) −x+2, −y+1, −z; (ii) x, −y−1/2, z−3/2; (iii) −x+2, y−1/2, −z+1/2.

Acknowledgements

The authors gratefully acknowledge financial support of this work by Yunyang Medical College (grant No. 2007ZQB24).

References

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