Ethyl 2-hydr­oxy-5-oxo-4-phenyl-2,3,4,5-tetra­hydro­pyrano[3,2-c]chromene-2-carboxyl­ate

Zhang, W.; Zhang, G.; Li, B.; Wang, Y.

doi:10.1107/S1600536809028311

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1969

doi:10.1107/S1600536809028311

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Ethyl 2-hydroxy-5-oxo-4-phenyl-2,3,4,5-tetrahydropyrano[3,2-c]chromene-2-carboxylate

Wei Zhang,^a Guangcun Zhang,^a Bailin Li ^a,^b and Yifeng Wang ^a ^*

^aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China, and ^bDepartment of Pharmaceutical and Chemical Engineering, Taizhou College, Linhai, Zhejiang 317000, People's Republic of China
^*Correspondence e-mail: yifengwang108@gmail.com

(Received 9 July 2009; accepted 17 July 2009; online 25 July 2009)

The main structural unit of the title compoud, C₂₁H₁₈O₆, is a fused three-ring group consisting of coumarin and tetrahydropyrane ring systems. Two C atoms of the tetrahydropyran ring are displaced by 0.295 (3) and −0.360 (2) Å from the mean plane of coumarin ring. The dihedral angle between the phenyl and coumarin rings is 73.94 (3)°. Intermolecular O—H⋯O hydrogen bonds are present in the crystal structure.

Related literature

For the synthesis of (E)-ethyl 2-oxo-4-phenylbut-3-enoate, see: Vaijayanthi & Chadha (2007 ).

Experimental

Crystal data

C₂₁H₁₈O₆
M_r = 366.37
Monoclinic, P 2₁ /n
a = 5.4988 (2) Å
b = 14.9975 (5) Å
c = 21.342 (1) Å
β = 98.5487 (13)°
V = 1740.48 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.41 × 0.39 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 2005 ) T_min = 0.954, T_max = 0.986
16523 measured reflections
3422 independent reflections
2568 reflections with F² > 2σ(F²)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.080
S = 1.00
3422 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H101⋯O2ⁱ	0.82	2.30	2.9198 (15)	132
O1—H101⋯O5	0.82	2.17	2.6628 (17)	119
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 2006 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ); program(s) used to solve structure: SHELXL97 (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: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028311/pk2181sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028311/pk2181Isup2.hkl

checkCIF report

Comment top

Coumarin derivatives are widely distributed in nature and are used as versatile intermediates in organic and natural product synthesis. Moreover, this class of compound possess a wide range of biological activities, including anticoagulant and HIV protease inhibition properties. The title compound, which is readily synthesized from commercially available 4-hydroxycoumarin and (E)-ethyl 2-oxo- 4-phenylbut-3-enoate, can act as an intermediate in organic and natural product synthesis. In this article, the crystal structure of the title compound, ethyl 2-hydroxy-5-oxo-4-phenyl-2,3,4,5-tetrahydropyrano[3,2- c]chromene-2-carboxylate was described (Fig. 1). The main structural unit is a three-ring group consisting of a coumarin ring and a tetrahydropyrane. Two carbon atoms of the tetrahydropyrane structure are not coplanar with the coumarin backbone: one carbon atom lies 0.295 (3) Å from the mean plane of coumarin ring and the other lies 0.360 (2) Å from the plane in opposite direction. The dihedral angle between benzene and coumarin rings is 73.94 (3) °. The distance from O1 of the hydroxyl group to coumarin plane is 1.664 (2) Å. In addition, intermolecular O—H···O hydrogen bonds in the crystal are observed (Fig. 2).

Related literature top

For the synthesis of (E)-ethyl 2-oxo-4-phenylbut-3-enoate, see: Vaijayanthi & Chadha (2007).

Experimental top

The title compound was synthesized by treating (E)-ethyl 2-oxo-4-phenylbut-3-enoate (2.04 g,10 mmol) with 4-hydroxycoumarin (1.62 g, 10 mmol) in the presence of triethylamine as a catalyst in dichloromethane (30 ml) under stirring at room temperature for 24 h. The solvent was distilled under vacuum, and the residue was purified by flash column chromatography (silica gel, Hex/AcOEt, v/v, 3:1) giving the title compound (3.3 g, 90%). The compound (E)-ethyl 2-oxo-4-phenylbut-3-enoate was obtained from commercially available benzaldehyde by condensation with pyruvic acid and subsequent esterification with ethanol. Suitable crystals of the title compound were obtained by slow evaporation of dichloromethane solution at room temperature.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (Rigaku, 2007); program(s) used to solve structure: SHELXL97 (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: CrystalStructure (Rigaku, 2007).

Figures top

	Fig. 1. The asymmetric unit of the structure of the title compound, with the atomic labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The molecular packing of the title compound showing H-bond interactions. Symmetry code (i) is 0.5-x, 0.5+y, 0.5-z.

Ethyl 2-hydroxy-5-oxo-4-phenyl-2,3,4,5- tetrahydropyrano[3,2-c]chromene-2-carboxylate top

Crystal data top

C₂₁H₁₈O₆	F(000) = 768.00
M_r = 366.37	D_x = 1.398 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 11365 reflections
a = 5.4988 (2) Å	θ = 3.2–27.4°
b = 14.9975 (5) Å	µ = 0.10 mm⁻¹
c = 21.342 (1) Å	T = 296 K
β = 98.5487 (13)°	Platelet, colorless
V = 1740.48 (12) Å³	0.41 × 0.39 × 0.14 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	2568 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.026
ω scans	θ_max = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 2005)	h = −7→7
T_min = 0.954, T_max = 0.986	k = −19→16
16523 measured reflections	l = −27→27
3422 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.035	w = 1/[σ²(F_o²) + (0.013P)² + P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.080	(Δ/σ)_max = 0.001
S = 1.00	Δρ_max = 0.21 e Å⁻³
3422 reflections	Δρ_min = −0.19 e Å⁻³
246 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008)
0 restraints	Extinction coefficient: 0.0057 (4)

Crystal data top

C₂₁H₁₈O₆	V = 1740.48 (12) Å³
M_r = 366.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.4988 (2) Å	µ = 0.10 mm⁻¹
b = 14.9975 (5) Å	T = 296 K
c = 21.342 (1) Å	0.41 × 0.39 × 0.14 mm
β = 98.5487 (13)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3422 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 2005)	2568 reflections with F² > 2σ(F²)
T_min = 0.954, T_max = 0.986	R_int = 0.026
16523 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
3422 reflections	Δρ_min = −0.19 e Å⁻³
246 parameters

Special details top

Geometry. The tetrahydropyrane structure in the crystal displays an envelope configuration, with atom C2 at the flap position, displaced by 0.603 (2) Å from the mean plane of the other atoms.

Refinement. Refinement using reflections with F² > 2.0 σ(F²). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.3270 (2)	0.47260 (6)	0.24846 (5)	0.0400 (2)
O2	0.3755 (2)	0.12605 (6)	0.19275 (5)	0.0442 (3)
O3	0.2981 (2)	0.39483 (6)	0.15453 (5)	0.0369 (2)
O4	0.7169 (2)	0.14798 (8)	0.25944 (6)	0.0548 (3)
O5	0.2708 (2)	0.60253 (9)	0.16249 (6)	0.0562 (3)
O6	0.5597 (2)	0.54329 (8)	0.11100 (6)	0.0483 (3)
C1	0.4400 (2)	0.46019 (10)	0.19571 (6)	0.0320 (3)
C2	0.7020 (2)	0.42864 (10)	0.21432 (8)	0.0344 (3)
C3	0.7153 (2)	0.33839 (10)	0.24884 (6)	0.0326 (3)
C4	0.5223 (2)	0.27767 (10)	0.21402 (6)	0.0322 (3)
C5	0.5514 (3)	0.18281 (11)	0.22491 (8)	0.0383 (3)
C6	0.1792 (3)	0.15776 (11)	0.15092 (6)	0.0390 (3)
C7	0.0084 (3)	0.09575 (12)	0.12389 (8)	0.0504 (4)
C8	−0.1910 (3)	0.12559 (12)	0.08244 (9)	0.0548 (5)
C9	−0.2214 (3)	0.21535 (12)	0.06798 (8)	0.0490 (4)
C10	−0.0505 (2)	0.27653 (11)	0.09506 (6)	0.0394 (3)
C11	0.1532 (2)	0.24823 (10)	0.13760 (6)	0.0335 (3)
C12	0.3355 (2)	0.30795 (10)	0.17075 (6)	0.0312 (3)
C13	0.7091 (2)	0.34673 (10)	0.31968 (6)	0.0334 (3)
C14	0.9040 (3)	0.38961 (12)	0.35684 (8)	0.0429 (4)
C15	0.9097 (3)	0.39905 (12)	0.42137 (9)	0.0526 (4)
C16	0.7198 (3)	0.36628 (13)	0.45022 (9)	0.0554 (5)
C17	0.5260 (3)	0.32322 (13)	0.41407 (9)	0.0526 (4)
C18	0.5209 (3)	0.31326 (12)	0.34917 (8)	0.0427 (4)
C19	0.4127 (2)	0.54477 (11)	0.15467 (8)	0.0368 (3)
C20	0.5607 (4)	0.62325 (13)	0.07224 (10)	0.0632 (5)
C21	0.7368 (4)	0.60702 (17)	0.02723 (11)	0.0822 (7)
H3	0.8750	0.3122	0.2443	0.039*
H7	0.0279	0.0354	0.1335	0.060*
H8	−0.3073	0.0848	0.0638	0.066*
H9	−0.3574	0.2343	0.0400	0.059*
H10	−0.0706	0.3367	0.0851	0.047*
H11	0.7910	0.4727	0.2421	0.041*
H12	0.7781	0.4226	0.1763	0.041*
H14	1.0325	0.4123	0.3378	0.051*
H15	1.0420	0.4276	0.4455	0.063*
H16	0.7223	0.3731	0.4936	0.066*
H17	0.3979	0.3007	0.4333	0.063*
H18	0.3898	0.2838	0.3253	0.051*
H101	0.2350	0.5159	0.2417	0.048*
H201	0.6127	0.6743	0.0988	0.076*
H202	0.3976	0.6341	0.0492	0.076*
H211	0.8950	0.5924	0.0504	0.099*
H212	0.7504	0.6597	0.0025	0.099*
H213	0.6791	0.5585	−0.0003	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0426 (6)	0.0374 (6)	0.0417 (6)	0.0076 (5)	0.0117 (5)	0.0020 (5)
O2	0.0565 (7)	0.0292 (5)	0.0443 (6)	−0.0051 (5)	−0.0012 (5)	0.0017 (5)
O3	0.0413 (6)	0.0266 (5)	0.0394 (6)	−0.0019 (4)	−0.0047 (4)	0.0001 (4)
O4	0.0603 (8)	0.0355 (6)	0.0628 (8)	0.0082 (6)	−0.0107 (6)	0.0050 (6)
O5	0.0556 (7)	0.0415 (7)	0.0723 (9)	0.0130 (6)	0.0120 (6)	0.0145 (6)
O6	0.0652 (8)	0.0371 (6)	0.0445 (7)	−0.0020 (5)	0.0149 (6)	0.0096 (5)
C1	0.0357 (8)	0.0282 (7)	0.0322 (8)	−0.0027 (6)	0.0054 (6)	−0.0020 (6)
C2	0.0326 (7)	0.0315 (8)	0.0393 (8)	−0.0032 (6)	0.0056 (6)	0.0008 (6)
C3	0.0293 (7)	0.0318 (8)	0.0364 (8)	0.0025 (6)	0.0041 (6)	−0.0009 (6)
C4	0.0358 (8)	0.0281 (7)	0.0329 (8)	−0.0006 (6)	0.0059 (6)	−0.0011 (6)
C5	0.0457 (9)	0.0324 (8)	0.0365 (8)	−0.0014 (7)	0.0053 (7)	−0.0002 (7)
C6	0.0492 (9)	0.0373 (9)	0.0303 (8)	−0.0064 (7)	0.0049 (7)	−0.0005 (6)
C7	0.0719 (12)	0.0364 (9)	0.0404 (10)	−0.0173 (9)	0.0005 (9)	0.0006 (7)
C8	0.0683 (12)	0.0529 (11)	0.0398 (10)	−0.0267 (10)	−0.0031 (9)	−0.0026 (8)
C9	0.0507 (10)	0.0559 (11)	0.0376 (9)	−0.0111 (9)	−0.0025 (7)	−0.0013 (8)
C10	0.0457 (9)	0.0386 (9)	0.0333 (8)	−0.0048 (7)	0.0040 (7)	−0.0014 (7)
C11	0.0401 (8)	0.0331 (8)	0.0276 (7)	−0.0054 (7)	0.0064 (6)	−0.0032 (6)
C12	0.0370 (8)	0.0273 (7)	0.0304 (7)	−0.0023 (6)	0.0089 (6)	−0.0010 (6)
C13	0.0335 (7)	0.0303 (8)	0.0355 (8)	0.0065 (6)	0.0016 (6)	0.0027 (6)
C14	0.0405 (9)	0.0452 (10)	0.0408 (9)	0.0015 (7)	−0.0014 (7)	−0.0003 (7)
C15	0.0515 (10)	0.0561 (11)	0.0445 (10)	0.0083 (9)	−0.0117 (8)	−0.0060 (8)
C16	0.0647 (12)	0.0645 (12)	0.0351 (9)	0.0220 (10)	0.0014 (9)	−0.0008 (9)
C17	0.0525 (10)	0.0642 (12)	0.0433 (10)	0.0116 (9)	0.0146 (8)	0.0081 (9)
C18	0.0394 (9)	0.0465 (10)	0.0416 (9)	0.0015 (7)	0.0042 (7)	0.0010 (7)
C19	0.0398 (8)	0.0317 (8)	0.0372 (9)	−0.0057 (7)	0.0005 (7)	0.0013 (6)
C20	0.0818 (14)	0.0490 (11)	0.0601 (13)	−0.0083 (10)	0.0147 (11)	0.0222 (9)
C21	0.1051 (19)	0.0793 (16)	0.0674 (15)	−0.0195 (14)	0.0301 (14)	0.0151 (13)

Geometric parameters (Å, º) top

O1—C1	1.3772 (19)	C13—C18	1.383 (2)
O2—C5	1.3906 (19)	C14—C15	1.380 (2)
O2—C6	1.3791 (18)	C15—C16	1.379 (2)
O3—C1	1.4623 (17)	C16—C17	1.379 (2)
O3—C12	1.3560 (18)	C17—C18	1.389 (2)
O4—C5	1.2019 (19)	C20—C21	1.482 (3)
O5—C19	1.194 (2)	O1—H101	0.822
O6—C19	1.321 (2)	C2—H11	0.970
O6—C20	1.457 (2)	C2—H12	0.970
C1—C2	1.512 (2)	C3—H3	0.980
C1—C19	1.536 (2)	C7—H7	0.930
C2—C3	1.538 (2)	C8—H8	0.930
C3—C4	1.508 (2)	C9—H9	0.930
C3—C13	1.522 (2)	C10—H10	0.930
C4—C5	1.447 (2)	C14—H14	0.930
C4—C12	1.353 (2)	C15—H15	0.930
C6—C7	1.385 (2)	C16—H16	0.930
C6—C11	1.389 (2)	C17—H17	0.930
C7—C8	1.377 (2)	C18—H18	0.930
C8—C9	1.386 (2)	C20—H201	0.970
C9—C10	1.378 (2)	C20—H202	0.970
C10—C11	1.399 (2)	C21—H211	0.960
C11—C12	1.448 (2)	C21—H212	0.960
C13—C14	1.392 (2)	C21—H213	0.960

C5—O2—C6	121.90 (12)	O5—C19—C1	122.00 (16)
C1—O3—C12	116.34 (10)	O6—C19—C1	111.72 (13)
C19—O6—C20	116.16 (14)	O6—C20—C21	106.91 (17)
O1—C1—O3	108.45 (12)	C1—O1—H101	107.7
O1—C1—C2	110.84 (12)	C1—C2—H11	108.8
O1—C1—C19	109.68 (12)	C1—C2—H12	108.8
O3—C1—C2	110.52 (12)	C3—C2—H11	108.8
O3—C1—C19	102.28 (11)	C3—C2—H12	108.8
C2—C1—C19	114.63 (13)	H11—C2—H12	109.5
C1—C2—C3	112.15 (12)	C2—C3—H3	106.5
C2—C3—C4	108.40 (11)	C4—C3—H3	106.5
C2—C3—C13	113.39 (12)	C13—C3—H3	106.5
C4—C3—C13	114.91 (12)	C6—C7—H7	120.8
C3—C4—C5	117.50 (12)	C8—C7—H7	120.8
C3—C4—C12	122.74 (13)	C7—C8—H8	119.4
C5—C4—C12	119.62 (13)	C9—C8—H8	119.4
O2—C5—O4	116.37 (14)	C8—C9—H9	119.9
O2—C5—C4	118.06 (13)	C10—C9—H9	119.9
O4—C5—C4	125.57 (14)	C9—C10—H10	120.0
O2—C6—C7	117.07 (14)	C11—C10—H10	120.0
O2—C6—C11	121.07 (13)	C13—C14—H14	119.4
C7—C6—C11	121.85 (14)	C15—C14—H14	119.4
C6—C7—C8	118.37 (16)	C14—C15—H15	119.9
C7—C8—C9	121.12 (17)	C16—C15—H15	119.9
C8—C9—C10	120.10 (15)	C15—C16—H16	120.3
C9—C10—C11	120.05 (15)	C17—C16—H16	120.3
C6—C11—C10	118.50 (13)	C16—C17—H17	119.8
C6—C11—C12	117.48 (12)	C18—C17—H17	119.8
C10—C11—C12	123.97 (13)	C13—C18—H18	119.7
O3—C12—C4	124.57 (13)	C17—C18—H18	119.7
O3—C12—C11	113.70 (12)	O6—C20—H201	110.1
C4—C12—C11	121.72 (13)	O6—C20—H202	110.1
C3—C13—C14	118.36 (14)	C21—C20—H201	110.1
C3—C13—C18	123.41 (13)	C21—C20—H202	110.1
C14—C13—C18	118.23 (14)	H201—C20—H202	109.5
C13—C14—C15	121.16 (16)	C20—C21—H211	109.5
C14—C15—C16	120.15 (16)	C20—C21—H212	109.5
C15—C16—C17	119.36 (17)	C20—C21—H213	109.5
C16—C17—C18	120.49 (18)	H211—C21—H212	109.5
C13—C18—C17	120.61 (15)	H211—C21—H213	109.5
O5—C19—O6	126.28 (16)	H212—C21—H213	109.5

C5—O2—C6—C7	−176.87 (15)	C3—C4—C5—O2	−179.57 (14)
C5—O2—C6—C11	2.1 (2)	C3—C4—C5—O4	−0.0 (2)
C6—O2—C5—O4	−178.82 (15)	C3—C4—C12—O3	−1.0 (2)
C6—O2—C5—C4	0.8 (2)	C3—C4—C12—C11	179.57 (14)
C1—O3—C12—C4	−12.7 (2)	C5—C4—C12—O3	−176.60 (15)
C1—O3—C12—C11	166.76 (13)	C5—C4—C12—C11	4.0 (2)
C12—O3—C1—O1	−79.87 (15)	C12—C4—C5—O2	−3.8 (2)
C12—O3—C1—C2	41.82 (17)	C12—C4—C5—O4	175.79 (17)
C12—O3—C1—C19	164.28 (13)	O2—C6—C7—C8	179.32 (16)
C19—O6—C20—C21	179.82 (15)	O2—C6—C11—C10	−179.62 (14)
C20—O6—C19—O5	5.1 (2)	O2—C6—C11—C12	−1.9 (2)
C20—O6—C19—C1	−175.90 (13)	C7—C6—C11—C10	−0.7 (2)
O1—C1—C2—C3	61.60 (16)	C7—C6—C11—C12	176.99 (16)
O1—C1—C19—O5	−14.1 (2)	C11—C6—C7—C8	0.4 (2)
O1—C1—C19—O6	166.88 (12)	C6—C7—C8—C9	−0.1 (2)
O3—C1—C2—C3	−58.67 (16)	C7—C8—C9—C10	0.1 (2)
O3—C1—C19—O5	100.86 (17)	C8—C9—C10—C11	−0.5 (2)
O3—C1—C19—O6	−78.16 (14)	C9—C10—C11—C6	0.8 (2)
C2—C1—C19—O5	−139.51 (16)	C9—C10—C11—C12	−176.80 (16)
C2—C1—C19—O6	41.46 (18)	C6—C11—C12—O3	179.34 (14)
C19—C1—C2—C3	−173.59 (12)	C6—C11—C12—C4	−1.2 (2)
C1—C2—C3—C4	43.95 (17)	C10—C11—C12—O3	−3.1 (2)
C1—C2—C3—C13	−84.91 (15)	C10—C11—C12—C4	176.41 (16)
C2—C3—C4—C5	160.47 (14)	C3—C13—C14—C15	−179.77 (15)
C2—C3—C4—C12	−15.2 (2)	C3—C13—C18—C17	−179.88 (15)
C2—C3—C13—C14	−64.76 (18)	C14—C13—C18—C17	0.7 (2)
C2—C3—C13—C18	115.79 (16)	C18—C13—C14—C15	−0.3 (2)
C4—C3—C13—C14	169.80 (14)	C13—C14—C15—C16	−0.4 (2)
C4—C3—C13—C18	−9.7 (2)	C14—C15—C16—C17	0.7 (2)
C13—C3—C4—C5	−71.53 (18)	C15—C16—C17—C18	−0.4 (3)
C13—C3—C4—C12	112.80 (17)	C16—C17—C18—C13	−0.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H101···O2ⁱ	0.82	2.30	2.9198 (15)	132
O1—H101···O5	0.82	2.17	2.6628 (17)	119

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈O₆
M_r	366.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	5.4988 (2), 14.9975 (5), 21.342 (1)
β (°)	98.5487 (13)
V (Å³)	1740.48 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.41 × 0.39 × 0.14

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 2005)
T_min, T_max	0.954, 0.986
No. of measured, independent and observed [F² > 2σ(F²)] reflections	16523, 3422, 2568
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.080, 1.00
No. of reflections	3422
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

Computer programs: PROCESS-AUTO (Rigaku, 2006), CrystalStructure (Rigaku, 2007), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H101···O2ⁱ	0.822	2.304	2.9198 (15)	132.2
O1—H101···O5	0.822	2.165	2.6628 (17)	119.0

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

We are grateful for the help of Professor Jian-Ming Gu of Zhejiang University.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Higashi, T. (2005). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2006). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2007). CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vaijayanthi, T. & Chadha, A. (2007). Tetrahedron Asymmetry, 18, 1077–1084. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 8| August 2009| Page o1969

doi:10.1107/S1600536809028311

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 2-hydr­­oxy-5-oxo-4-phenyl-2,3,4,5-tetra­hydro­pyrano[3,2-c]chromene-2-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 2-hydroxy-5-oxo-4-phenyl-2,3,4,5-tetrahydropyrano[3,2-c]chromene-2-carboxylate