9-Eth­oxy-1,5,13-trimethyl-8,10-dioxa­tetra­cyclo­[7.7.1.02,7.011,16]hepta­deca-2,4,6,11,13,15-hexa­ene

Nowakowska-Bogdan, E.M.; Wicher, E.; Ejsmont, K.; Zaleski, J.

doi:10.1107/S1600536809032747

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2228

doi:10.1107/S1600536809032747

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9-Ethoxy-1,5,13-trimethyl-8,10-dioxatetracyclo[7.7.1.0^2,7.0^11,16]heptadeca-2,4,6,11,13,15-hexaene

Ewa Maria Nowakowska-Bogdan,^a ^* Ewa Wicher,^a Krzysztof Ejsmont ^b and Jacek Zaleski ^b

^aInstitute of Heavy Organic Synthesis "Blachownia", Energetyków 9, 47-225 Kędzierzyn–Koźle, Poland, and ^bFaculty of Chemistry, University of Opole, Oleska 48, 45-052 Opole, Poland
^*Correspondence e-mail: nowakowska.e@icso.com.pl

(Received 15 June 2009; accepted 17 August 2009; online 22 August 2009)

The reaction of ethyl acetoacetate with meta-cresol in an acidic ionic liquid yielded a complex mixture of condensation products. 4,7-Dimethylcoumarin and the title compound, C₂₀H₂₂O₃, were isolated. The title compound shows chemical but not crystallographic mirror symmetry. The two aromatic rings are inclined at an angle of 73.55 (6)°.

Related literature

For related structures, see: Klei et al. (1995 ); Vijayalakshmi et al. (2001 ).

Experimental

Crystal data

C₂₀H₂₂O₃
M_r = 310.38
Monoclinic, P 2₁ /c
a = 14.3718 (6) Å
b = 11.6446 (5) Å
c = 10.2260 (4) Å
β = 96.901 (4)°
V = 1698.96 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 90 K
0.25 × 0.20 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: none
9989 measured reflections
2985 independent reflections
1751 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.126
S = 0.95
2985 reflections
252 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032747/bt2970sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032747/bt2970Isup2.hkl

checkCIF report

Related literature top

For related structures, see: Klei et al. (1995); Vijayalakshmi et al. (2001).

Experimental top

Anhydrous aluminium chloride (16.0 g, 60 mmol of Al₂Cl₆) and 1-n-butyl-3-methyl-imidazolium chloride (10.5 g, 60 mmol of [bmim]Cl) were mixed under dry nitrogen atmosphere. Ionic liquid ([bmim] Al₂Cl₇) was formed in the exothermic reaction of two solid substrates. The melt of meta-cresol (6.3 ml, 60 mmol) and ethyl acetoacetate (7.5 ml, 60 mmol) was dissolved in the ionic liquid and maintained at ambient temperature for 5 days. A yellow, viscous liquid was poured on ice and an opaque solution was extracted twice with methylene chloride. The organic solution was extracted with diluted sulfuric acid (25 ml of 3M H₂SO₄) and water to remove aluminium compounds. It was dried over anhydrous magnesium sulfate and adsorbed on silica gel (Kieselgel H, Fluka). The crude reaction mixture was chromatographed on the short column (5.5 by 15 cm) using benzene as the eluent. The first fraction, after evaporation and crystallization from n-hexane, gave title compound (I) (1.11 g, 12%) as colourless prisms, m.p. 146–153°C. Recrystallization from isooctane raised m.p. to 153–155°C, the crystals were suitable for X-ray diffraction studies. MS, m/z (int.): 310 (38, M⁺), 295 (100), 281 (5), 267 (78), 264 (5), 249 (7), 239 (8), 223 (11), 203 (27), 175 (26). FTIR (KBr): 3037 (aromatic protons); 2985, 2969, 2937, 2909 (aliphatic C–H stretching vibrations); 1623, 1580, 1506 (benzene ring stretching); 1271, 1157, 1127, 1090, 1050, 1008 (C–O–C stretching vibrations); 886, 814 (out of plane hydrogen wagging in aromatic rings). ¹H-NMR (DMSO-d6): 7.26, d 3 J = 7.4 Hz, 2H and 6.70, d ³J = 7.4 Hz, 2H (vicinal aromatic protons); 6.63, s, 2H (isolated aromatic protons); 4.04, q, ³J = 6.7 Hz, 2H and 1.26, t, 3 J = 6.7 Hz, 3H (O-ethyl group); 2.21, s, 2H (methylene bridge); 2.16, s, 6H (methyl groups bound to aromatic rings); 1.76, s, 3H (methyl group). ¹³C-NMR (CDCl₃): 151.8 (C4, C16); 137.8 (C6, C14); 127.5 (C9, C11); 123.8 (C8, C12); 122.6 (C7, C13); 117.1 (C5, C15); 112.1 (C2); 58.5 and 15.7 (O-ethyl group); 38.8 (methylene bridge); 34.8 (C10); 21.1 (methyl groups on aromatic rings). The next fraction provided 4,7-dimethyl-coumarin as white crystals (1.32 g, 12.6%); m.p. 135–136°C (n-hexane). From the last fraction small amounts of 1,2-dihydro-4,7-dimethyl-4-(4-hydroxy-2-methylphenyl)-coumarin (isomer 2) were isolated (m.p. 211–212°C).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing 50% displacement ellipsoids (arbitrary spheres for the H atoms).

9-Ethoxy-1,5,13-trimethyl-8,10-dioxatetracyclo[7.7.1.0^2,7.0^11,16]heptadeca- 2,4,6,11,13,15-hexaene top

Crystal data top

C₂₀H₂₂O₃	F(000) = 664
M_r = 310.38	D_x = 1.213 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2985 reflections
a = 14.3718 (6) Å	θ = 2.7–25.0°
b = 11.6446 (5) Å	µ = 0.08 mm⁻¹
c = 10.2260 (4) Å	T = 90 K
β = 96.901 (4)°	Plate, colourless
V = 1698.96 (12) Å³	0.25 × 0.20 × 0.10 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer	1751 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 25.0°, θ_min = 2.7°
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm^-1	h = −17→17
ω scans	k = −13→13
9989 measured reflections	l = −12→6
2985 independent reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0723P)²] where P = (F_o² + 2F_c²)/3
2985 reflections	(Δ/σ)_max < 0.001
252 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₂₂O₃	V = 1698.96 (12) Å³
M_r = 310.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.3718 (6) Å	µ = 0.08 mm⁻¹
b = 11.6446 (5) Å	T = 90 K
c = 10.2260 (4) Å	0.25 × 0.20 × 0.10 mm
β = 96.901 (4)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	1751 reflections with I > 2σ(I)
9989 measured reflections	R_int = 0.031
2985 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.27 e Å⁻³
2985 reflections	Δρ_min = −0.23 e Å⁻³
252 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	0.24961 (15)	0.47696 (17)	0.2890 (2)	0.0235 (5)
O1A	0.20501 (9)	0.37104 (11)	0.26845 (13)	0.0263 (4)
C1B	0.17179 (18)	0.3422 (2)	0.1307 (2)	0.0317 (6)
C1C	0.13069 (17)	0.22326 (18)	0.1300 (2)	0.0379 (6)
H1C1	0.1089	0.2012	0.0411	0.057*
H1C2	0.0791	0.2226	0.1816	0.057*
H1C3	0.1778	0.1701	0.1668	0.057*
O2	0.33294 (10)	0.47258 (12)	0.22253 (13)	0.0288 (4)
C3	0.40517 (14)	0.55031 (17)	0.26325 (19)	0.0226 (5)
C4	0.48180 (15)	0.55002 (18)	0.1881 (2)	0.0236 (5)
C5	0.55726 (14)	0.62572 (17)	0.21702 (19)	0.0236 (5)
C5A	0.64239 (15)	0.62257 (19)	0.1394 (2)	0.0294 (5)
H51	0.6221	0.6032	0.0492	0.044*
H52	0.6862	0.5660	0.1771	0.044*
H53	0.6720	0.6966	0.1433	0.044*
C6	0.55384 (16)	0.70296 (18)	0.3227 (2)	0.0271 (5)
C7	0.47795 (15)	0.70088 (18)	0.3991 (2)	0.0253 (5)
C7A	0.40231 (14)	0.62393 (17)	0.37198 (18)	0.0222 (5)
C8	0.31708 (14)	0.62109 (17)	0.45321 (19)	0.0218 (5)
C8A	0.34643 (15)	0.64395 (18)	0.60163 (19)	0.0276 (5)
H81	0.2923	0.6397	0.6480	0.041*
H82	0.3738	0.7190	0.6129	0.041*
H83	0.3914	0.5873	0.6360	0.041*
C9A	0.24205 (14)	0.70553 (17)	0.38933 (19)	0.0226 (5)
C9	0.23106 (15)	0.81749 (18)	0.4337 (2)	0.0256 (5)
C10	0.16298 (15)	0.89076 (19)	0.3686 (2)	0.0256 (5)
C11	0.10309 (14)	0.85430 (17)	0.2566 (2)	0.0244 (5)
C11A	0.03150 (16)	0.93435 (19)	0.1825 (2)	0.0341 (6)
H111	−0.0282	0.8965	0.1681	0.051*
H112	0.0515	0.9543	0.0992	0.051*
H113	0.0260	1.0027	0.2334	0.051*
C12	0.11309 (15)	0.74147 (18)	0.2120 (2)	0.0240 (5)
C13	0.18201 (14)	0.66987 (17)	0.27796 (19)	0.0225 (5)
O14	0.18724 (10)	0.56098 (11)	0.22264 (13)	0.0272 (4)
C15	0.27228 (16)	0.50062 (18)	0.4352 (2)	0.0240 (5)
H1B1	0.2258 (16)	0.3455 (18)	0.076 (2)	0.043 (7)*
H1B2	0.1230 (15)	0.4022 (18)	0.094 (2)	0.033 (6)*
H4A	0.4837 (14)	0.4925 (18)	0.116 (2)	0.028 (6)*
H6A	0.6069 (14)	0.7588 (18)	0.3474 (19)	0.025 (5)*
H7A	0.4784 (14)	0.7539 (18)	0.472 (2)	0.027 (6)*
H9A	0.2729 (14)	0.8461 (17)	0.515 (2)	0.028 (6)*
H10A	0.1543 (14)	0.9711 (18)	0.403 (2)	0.031 (6)*
H12A	0.0748 (17)	0.7141 (19)	0.133 (2)	0.044 (7)*
H15A	0.3208 (15)	0.4429 (19)	0.477 (2)	0.035 (6)*
H15B	0.2132 (16)	0.4963 (17)	0.480 (2)	0.032 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0254 (12)	0.0176 (11)	0.0280 (11)	−0.0014 (9)	0.0055 (9)	0.0029 (9)
O1A	0.0305 (9)	0.0197 (8)	0.0285 (8)	−0.0036 (7)	0.0028 (7)	−0.0012 (6)
C1B	0.0363 (14)	0.0266 (13)	0.0319 (12)	−0.0039 (11)	0.0023 (11)	−0.0039 (10)
C1C	0.0399 (15)	0.0277 (14)	0.0451 (15)	0.0006 (11)	0.0005 (12)	−0.0074 (11)
O2	0.0273 (8)	0.0280 (9)	0.0324 (8)	−0.0055 (7)	0.0085 (7)	−0.0072 (7)
C3	0.0233 (12)	0.0188 (11)	0.0248 (11)	0.0009 (9)	−0.0014 (9)	0.0015 (9)
C4	0.0259 (12)	0.0221 (12)	0.0225 (11)	0.0016 (9)	0.0015 (9)	−0.0008 (9)
C5	0.0229 (11)	0.0227 (12)	0.0246 (11)	0.0031 (10)	0.0003 (9)	0.0041 (9)
C5A	0.0280 (12)	0.0323 (13)	0.0279 (12)	−0.0039 (10)	0.0031 (10)	−0.0008 (10)
C6	0.0273 (13)	0.0218 (12)	0.0311 (12)	−0.0017 (10)	−0.0004 (10)	0.0003 (10)
C7	0.0307 (13)	0.0207 (12)	0.0243 (11)	0.0014 (10)	0.0024 (10)	−0.0015 (9)
C7A	0.0244 (11)	0.0203 (11)	0.0214 (11)	0.0032 (9)	0.0014 (9)	0.0027 (9)
C8	0.0228 (11)	0.0195 (11)	0.0235 (11)	−0.0008 (9)	0.0045 (9)	0.0001 (9)
C8A	0.0309 (12)	0.0272 (13)	0.0254 (11)	0.0037 (10)	0.0068 (10)	0.0010 (10)
C9A	0.0243 (12)	0.0203 (11)	0.0237 (11)	−0.0001 (9)	0.0053 (9)	0.0002 (9)
C9	0.0306 (13)	0.0245 (12)	0.0224 (11)	−0.0017 (10)	0.0060 (10)	−0.0003 (10)
C10	0.0302 (12)	0.0192 (12)	0.0291 (12)	0.0022 (10)	0.0105 (10)	−0.0011 (10)
C11	0.0230 (11)	0.0218 (12)	0.0292 (11)	0.0002 (9)	0.0060 (9)	0.0038 (9)
C11A	0.0331 (13)	0.0281 (13)	0.0407 (13)	0.0029 (11)	0.0023 (11)	0.0058 (10)
C12	0.0215 (12)	0.0226 (12)	0.0281 (12)	−0.0022 (10)	0.0036 (10)	0.0030 (9)
C13	0.0276 (12)	0.0174 (11)	0.0239 (10)	−0.0001 (9)	0.0084 (9)	−0.0005 (9)
O14	0.0340 (9)	0.0214 (8)	0.0251 (8)	0.0031 (7)	−0.0007 (7)	−0.0010 (6)
C15	0.0247 (12)	0.0221 (12)	0.0258 (11)	0.0006 (10)	0.0054 (10)	0.0016 (9)

Geometric parameters (Å, º) top

C1—O1A	1.394 (2)	C7—H7A	0.97 (2)
C1—O14	1.441 (2)	C7A—C8	1.561 (3)
C1—O2	1.447 (2)	C8—C9A	1.545 (3)
C1—C15	1.516 (3)	C8—C15	1.545 (3)
O1A—C1B	1.471 (3)	C8—C8A	1.549 (3)
C1B—C1C	1.506 (3)	C8A—H81	0.9600
C1B—H1B1	1.01 (2)	C8A—H82	0.9600
C1B—H1B2	1.03 (2)	C8A—H83	0.9600
C1C—H1C1	0.9600	C9A—C9	1.396 (3)
C1C—H1C2	0.9600	C9A—C13	1.406 (3)
C1C—H1C3	0.9600	C9—C10	1.404 (3)
O2—C3	1.402 (2)	C9—H9A	1.02 (2)
C3—C7A	1.408 (3)	C10—C11	1.412 (3)
C3—C4	1.417 (3)	C10—H10A	1.01 (2)
C4—C5	1.401 (3)	C11—C12	1.404 (3)
C4—H4A	1.00 (2)	C11—C11A	1.521 (3)
C5—C6	1.412 (3)	C11A—H111	0.9600
C5—C5A	1.537 (3)	C11A—H112	0.9600
C5A—H51	0.9600	C11A—H113	0.9600
C5A—H52	0.9600	C12—C13	1.404 (3)
C5A—H53	0.9600	C12—H12A	0.97 (2)
C6—C7	1.416 (3)	C13—O14	1.394 (2)
C6—H6A	1.01 (2)	C15—H15A	1.03 (2)
C7—C7A	1.410 (3)	C15—H15B	1.01 (2)

O1A—C1—O14	106.32 (16)	C9A—C8—C15	105.53 (16)
O1A—C1—O2	106.81 (16)	C9A—C8—C8A	113.52 (16)
O14—C1—O2	107.79 (15)	C15—C8—C8A	109.48 (16)
O1A—C1—C15	110.49 (16)	C9A—C8—C7A	108.30 (15)
O14—C1—C15	112.89 (17)	C15—C8—C7A	107.35 (16)
O2—C1—C15	112.18 (17)	C8A—C8—C7A	112.28 (16)
C1—O1A—C1B	115.89 (15)	C8—C8A—H81	109.5
O1A—C1B—C1C	107.24 (18)	C8—C8A—H82	109.5
O1A—C1B—H1B1	109.9 (12)	H81—C8A—H82	109.5
C1C—C1B—H1B1	111.0 (13)	C8—C8A—H83	109.5
O1A—C1B—H1B2	109.0 (12)	H81—C8A—H83	109.5
C1C—C1B—H1B2	111.9 (12)	H82—C8A—H83	109.5
H1B1—C1B—H1B2	107.7 (17)	C9—C9A—C13	117.17 (19)
C1B—C1C—H1C1	109.5	C9—C9A—C8	123.89 (19)
C1B—C1C—H1C2	109.5	C13—C9A—C8	118.92 (17)
H1C1—C1C—H1C2	109.5	C9A—C9—C10	120.9 (2)
C1B—C1C—H1C3	109.5	C9A—C9—H9A	119.4 (11)
H1C1—C1C—H1C3	109.5	C10—C9—H9A	119.7 (11)
H1C2—C1C—H1C3	109.5	C9—C10—C11	121.6 (2)
C3—O2—C1	117.55 (15)	C9—C10—H10A	120.4 (12)
O2—C3—C7A	122.45 (18)	C11—C10—H10A	118.0 (12)
O2—C3—C4	115.67 (17)	C12—C11—C10	117.93 (19)
C7A—C3—C4	121.88 (19)	C12—C11—C11A	120.07 (19)
C5—C4—C3	121.08 (19)	C10—C11—C11A	121.97 (19)
C5—C4—H4A	119.3 (12)	C11—C11A—H111	109.5
C3—C4—H4A	119.6 (12)	C11—C11A—H112	109.5
C4—C5—C6	117.72 (19)	H111—C11A—H112	109.5
C4—C5—C5A	121.32 (18)	C11—C11A—H113	109.5
C6—C5—C5A	120.93 (18)	H111—C11A—H113	109.5
C5—C5A—H51	109.5	H112—C11A—H113	109.5
C5—C5A—H52	109.5	C13—C12—C11	119.6 (2)
H51—C5A—H52	109.5	C13—C12—H12A	120.0 (14)
C5—C5A—H53	109.5	C11—C12—H12A	120.4 (14)
H51—C5A—H53	109.5	O14—C13—C12	114.50 (18)
H52—C5A—H53	109.5	O14—C13—C9A	122.64 (18)
C5—C6—C7	120.8 (2)	C12—C13—C9A	122.85 (19)
C5—C6—H6A	120.4 (11)	C13—O14—C1	119.16 (15)
C7—C6—H6A	118.8 (11)	C1—C15—C8	108.64 (17)
C7A—C7—C6	121.9 (2)	C1—C15—H15A	110.6 (12)
C7A—C7—H7A	119.4 (12)	C8—C15—H15A	107.0 (12)
C6—C7—H7A	118.7 (12)	C1—C15—H15B	110.1 (12)
C3—C7A—C7	116.55 (19)	C8—C15—H15B	110.6 (12)
C3—C7A—C8	120.42 (18)	H15A—C15—H15B	109.9 (17)
C7—C7A—C8	122.99 (17)

O14—C1—O1A—C1B	52.0 (2)	C8A—C8—C9A—C9	27.8 (3)
O2—C1—O1A—C1B	−62.9 (2)	C7A—C8—C9A—C9	−97.6 (2)
C15—C1—O1A—C1B	174.86 (18)	C15—C8—C9A—C13	−33.8 (2)
C1—O1A—C1B—C1C	177.22 (17)	C8A—C8—C9A—C13	−153.74 (18)
O1A—C1—O2—C3	−159.04 (15)	C7A—C8—C9A—C13	80.8 (2)
O14—C1—O2—C3	87.06 (19)	C13—C9A—C9—C10	−0.3 (3)
C15—C1—O2—C3	−37.8 (2)	C8—C9A—C9—C10	178.18 (18)
C1—O2—C3—C7A	5.5 (3)	C9A—C9—C10—C11	0.2 (3)
C1—O2—C3—C4	−174.66 (17)	C9—C10—C11—C12	0.4 (3)
O2—C3—C4—C5	178.45 (17)	C9—C10—C11—C11A	−177.78 (19)
C7A—C3—C4—C5	−1.7 (3)	C10—C11—C12—C13	−0.8 (3)
C3—C4—C5—C6	−0.6 (3)	C11A—C11—C12—C13	177.37 (19)
C3—C4—C5—C5A	177.54 (18)	C11—C12—C13—O14	−178.21 (17)
C4—C5—C6—C7	2.0 (3)	C11—C12—C13—C9A	0.7 (3)
C5A—C5—C6—C7	−176.14 (19)	C9—C9A—C13—O14	178.71 (18)
C5—C6—C7—C7A	−1.2 (3)	C8—C9A—C13—O14	0.1 (3)
O2—C3—C7A—C7	−177.66 (17)	C9—C9A—C13—C12	−0.1 (3)
C4—C3—C7A—C7	2.5 (3)	C8—C9A—C13—C12	−178.73 (18)
O2—C3—C7A—C8	0.3 (3)	C12—C13—O14—C1	−174.43 (17)
C4—C3—C7A—C8	−179.47 (18)	C9A—C13—O14—C1	6.6 (3)
C6—C7—C7A—C3	−1.1 (3)	O1A—C1—O14—C13	144.54 (16)
C6—C7—C7A—C8	−179.04 (18)	O2—C1—O14—C13	−101.23 (18)
C3—C7A—C8—C9A	−88.6 (2)	C15—C1—O14—C13	23.2 (2)
C7—C7A—C8—C9A	89.3 (2)	O1A—C1—C15—C8	−177.26 (16)
C3—C7A—C8—C15	24.9 (2)	O14—C1—C15—C8	−58.4 (2)
C7—C7A—C8—C15	−157.21 (19)	O2—C1—C15—C8	63.7 (2)
C3—C7A—C8—C8A	145.29 (18)	C9A—C8—C15—C1	61.0 (2)
C7—C7A—C8—C8A	−36.8 (3)	C8A—C8—C15—C1	−176.52 (17)
C15—C8—C9A—C9	147.7 (2)	C7A—C8—C15—C1	−54.4 (2)

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂O₃
M_r	310.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	90
a, b, c (Å)	14.3718 (6), 11.6446 (5), 10.2260 (4)
β (°)	96.901 (4)
V (Å³)	1698.96 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.20 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9989, 2985, 1751
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.126, 0.95
No. of reflections	2985
No. of parameters	252
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.23

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

Klei, H. E., Callegari, E., Edwards, J. M. & Kelly, J. A. (1995). Acta Cryst. C51, 2621–2624. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vijayalakshmi, L., Parthasarathi, V., Dodia, N. & Shah, A. (2001). Acta Cryst. E57, o212–o213. Web of Science CSD CrossRef IUCr Journals Google Scholar

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