2-Oxo-2H-chromen-4-yl 4-tert-butyl­benzoate

Abou, A.; Sessouma, B.; Djandé, A.; Saba, A.; Kakou-Yao, R.

doi:10.1107/S160053681200298X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o537-o538

doi:10.1107/S160053681200298X

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2-Oxo-2H-chromen-4-yl 4-tert-butylbenzoate

Akoun Abou,^a ^* Bintou Sessouma,^b Abdoulaye Djandé,^b Adama Saba ^b and Rita Kakou-Yao ^a

^aLaboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody, 22 BP 582, Abidjan 22, Cote d'Ivoire, and ^bLaboratoire de Chimie Bio-organique et Phytochimie, Université de Ouagadougou, 03 BP 7021, Ouagadougou 03, Burkina Faso
^*Correspondence e-mail: abou_akoun@yahoo.fr

(Received 6 January 2012; accepted 24 January 2012; online 31 January 2012)

In the title molecule, C₂₀H₁₈O₄, the three methyl groups of the tert-butyl substituent show rotational disorder. Each methyl group is split over three positions, with refined site-occupation factors of 0.711 (4), 0.146 (3) and 0.144 (4). The benzene ring of the benzoate group is oriented at a dihedral angle of 60.70 (7)° with respect to the planar chromene ring [maximum deviation = 0.046 (2) Å]. The crystal structure features centrosymmetric R₂²(8) dimers formed via C—H⋯O interactions, and these dimeric aggregates are connected by C—H⋯π interactions.

Related literature

For the biological activities of coumarin derivatives, see: Ukhov et al. (2001 ); Abd Elhafez et al. (2003 ); Basanagouda et al. (2009 ); Liu et al. (2008 ); Trapkov et al. (1996 ); Vukovic et al. (2010 ); Emmanuel-Giota et al. (2001 ); Hamdi & Dixneuf (2007 ); Wang et al. (2001 ); Marchenko et al. (2006 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₁₈O₄
M_r = 322.34
Triclinic, $[P \overline 1]$
a = 6.4319 (2) Å
b = 9.3498 (3) Å
c = 14.5505 (5) Å
α = 98.481 (1)°
β = 93.655 (1)°
γ = 102.359 (2)°
V = 841.27 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.50 × 0.30 × 0.14 mm

Data collection

Nonius KappaCCD diffractometer
11164 measured reflections
4198 independent reflections
2926 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.157
S = 1.05
4198 reflections
247 parameters
10 restraints
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the chromene benzene and benzoate benzene rings.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.93	2.39	3.323 (2)	177
C18B—H18D⋯Cg3ⁱⁱ	0.96	2.83	3.54 (2)	133
C18C—H18I⋯Cg3ⁱⁱ	0.96	2.90	3.47 (2)	119
C19C—H19I⋯Cg2ⁱⁱⁱ	0.96	2.95	3.75 (2)	141
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+1, -z; (iii) x-1, y+1, z.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97, publCIF (Westrip, 2010 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681200298X/bh2408sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200298X/bh2408Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681200298X/bh2408Isup3.cml

checkCIF report

Comment top

Coumarin constitutes one of the major classes of naturally occurring compounds, and interest in its chemistry continues unabated because of its usefulness as biologically active agents. It also represents the core structure of several molecules of pharmaceutical importance. Coumarin and its derivatives have been reported to serve as anti-bacterial (Ukhov et al., 2001; Abd Elhafez et al., 2003; Basanagouda et al., 2009; Liu et al., 2008), anti-oxidant (Trapkov et al., 1996; Vukovic et al., 2010), anti-inflammatory (Emmanuel-Giota et al., 2001; Hamdi & Dixneuf, 2007), anti-coagulant (Hamdi & Dixneuf, 2007) and anti-tumour (Wang et al., 2001; Marchenko, et al., 2006) agents. Therefore, the synthesis of new coumarin derivatives is of considerable interest. In order to study the influence of new substituents on the activity of the coumarin derivatives, the title compound has been synthesized and in this paper, we present its molecular and crystal structure.

In the title compound (Fig. 1), the three methyl groups of the tert-butyl substituent exhibit rotational disorder, with refined site occupation factors of 0.711 (4), 0.146 (3) and 0.144 (4). The planar chromene ring system resulting from the two fused rings (benzene and 3,6-dihydro-2H-pyran) is oriented with respect to the benzoate-benzene ring at a dihedral angle of 60.70 (7)°.

In the crystal structure, intermolecular C—H···O interactions (Table 1) link the molecules into centrosymmetric dimers through R₂²(8) ring motifs (Bernstein et al., 1995) and these dimeric aggregates are connected by C—H···π and weak C═O···π interactions (Table 1, Fig. 2 and 3).

Related literature top

For the biological activities of coumarin derivatives, see: Ukhov et al. (2001); Abd Elhafez et al. (2003); Basanagouda et al. (2009); Liu et al. (2008); Trapkov et al. (1996); Vukovic et al. (2010); Emmanuel-Giota et al. (2001); Hamdi & Dixneuf (2007); Wang et al. (2001); Marchenko et al. (2006). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

To a solution of 4-tertiobutylbenzoyl chloride (4.10^-2 mole) in dried tetrahydrofuran (150 ml), was added dried triethylamine (0.12 mole) and 4-hydroxycoumarin (4.10^-2 mole) by small portions over 30 min. The mixture was then refluxed for 3 h and poured in 300 ml of chloroform. The solution was acidified with dilute hydrochloric acid until the pH was 2–3. The organic layer was extracted, washed with water, dried over MgSO₄ and the solvent removed. The crude product was recrystallized from chloroform. Colourless crystals of the title compound were obtained in good yield 73.8%; melting point: 381–383 K.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), publCIF (Westrip, 2010) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compund, showing displacement ellipsoids at the 50% probability level. H atoms are shown as spheres of arbitrary radius.
	Fig. 2. Crystal packing, viewed down the a axis, showing centrosymmetric dimers linked by C—H···π interactions. The green dots are centroids of rings and the dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonds have been omitted for clarity.
	Fig. 3. Crystal packing, showing parallel centrosymmetric dimers linked by C═O···π interactions. The green dots are centroids of rings and the dashed lines indicate hydrogen bonds and O···π contacts. H atoms not involved in hydrogen bonds have been omitted for clarity.

2-Oxo-2H-chromen-4-yl 4-tert-butylbenzoate top

Crystal data top

C₂₀H₁₈O₄	Z = 2
M_r = 322.34	F(000) = 340
Triclinic, P1	D_x = 1.273 Mg m⁻³
Hall symbol: -P 1	Melting point = 381–383 K
a = 6.4319 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3498 (3) Å	Cell parameters from 11164 reflections
c = 14.5505 (5) Å	θ = 2.8–29.0°
α = 98.481 (1)°	µ = 0.09 mm⁻¹
β = 93.655 (1)°	T = 298 K
γ = 102.359 (2)°	Parallelepiped, colourless
V = 841.27 (5) Å³	0.50 × 0.30 × 0.14 mm

Data collection top

Nonius KappaCCD diffractometer	2926 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 29.0°, θ_min = 2.8°
ϕ and ω scans	h = −8→8
11164 measured reflections	k = −12→12
4198 independent reflections	l = −19→19

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0589P)² + 0.1855P] where P = (F_o² + 2F_c²)/3
4198 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.18 e Å⁻³
10 restraints	Δρ_min = −0.16 e Å⁻³
108 constraints

Crystal data top

C₂₀H₁₈O₄	γ = 102.359 (2)°
M_r = 322.34	V = 841.27 (5) Å³
Triclinic, P1	Z = 2
a = 6.4319 (2) Å	Mo Kα radiation
b = 9.3498 (3) Å	µ = 0.09 mm⁻¹
c = 14.5505 (5) Å	T = 298 K
α = 98.481 (1)°	0.50 × 0.30 × 0.14 mm
β = 93.655 (1)°

Data collection top

Nonius KappaCCD diffractometer	2926 reflections with I > 2σ(I)
11164 measured reflections	R_int = 0.033
4198 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	10 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 1.05	Δρ_max = 0.18 e Å⁻³
4198 reflections	Δρ_min = −0.16 e Å⁻³
247 parameters

Special details top

Refinement. In the title coumpound, the tert-butyl group may rotate virtually freely at least at room temperature, and in the spatial average one sees this group as a rotational toroid. Since it is hard to describe this situation to the refinement program, we have reduced the problem to a refinement of only three sites per methyl group (see Refinement section). The low U_eq as compared to neighbors for atom C17 is caused by this disorder.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.44961 (18)	1.29961 (11)	0.47812 (8)	0.0616 (3)
C14	0.3413 (2)	0.39183 (15)	0.12787 (10)	0.0501 (3)
O3	0.41921 (18)	0.87715 (12)	0.33682 (9)	0.0691 (4)
O2	0.1580 (2)	1.22217 (14)	0.54429 (9)	0.0740 (4)
C4	0.6027 (2)	1.13127 (16)	0.37549 (10)	0.0534 (4)
C12	0.4620 (3)	0.60660 (18)	0.24953 (12)	0.0651 (5)
H12	0.5638	0.6592	0.2978	0.078*
O4	0.1052 (2)	0.85839 (15)	0.25363 (10)	0.0838 (4)
C5	0.6076 (3)	1.27317 (17)	0.42286 (11)	0.0545 (4)
C11	0.2870 (2)	0.66128 (15)	0.22615 (10)	0.0497 (3)
C16	0.1363 (3)	0.57977 (18)	0.15545 (12)	0.0623 (4)
H16	0.0149	0.6138	0.1402	0.075*
C13	0.4863 (3)	0.47264 (18)	0.20086 (12)	0.0671 (5)
H13	0.6042	0.4362	0.2180	0.080*
C2	0.2658 (3)	1.04280 (16)	0.43723 (12)	0.0590 (4)
H2	0.1486	0.9663	0.4403	0.071*
C10	0.2528 (3)	0.80567 (16)	0.27141 (11)	0.0537 (4)
C17	0.3724 (3)	0.24640 (16)	0.07275 (11)	0.0551 (4)
C15	0.1651 (3)	0.44763 (18)	0.10713 (12)	0.0628 (4)
H15	0.0626	0.3948	0.0592	0.075*
C6	0.7699 (3)	1.39340 (19)	0.41635 (13)	0.0679 (5)
H6	0.7691	1.4877	0.4473	0.081*
C3	0.4194 (2)	1.01742 (16)	0.38416 (11)	0.0550 (4)
C9	0.7722 (3)	1.1114 (2)	0.32308 (12)	0.0681 (5)
H9	0.7745	1.0176	0.2919	0.082*
C1	0.2803 (3)	1.18853 (17)	0.49010 (12)	0.0575 (4)
C8	0.9354 (3)	1.2308 (3)	0.31767 (14)	0.0803 (6)
H8	1.0485	1.2174	0.2831	0.096*
C7	0.9322 (3)	1.3711 (2)	0.36341 (15)	0.0780 (5)
H7	1.0420	1.4513	0.3581	0.094*
C18A	0.2652 (7)	0.2152 (4)	−0.0279 (2)	0.0881 (11)	0.711 (4)
H18A	0.3211	0.2965	−0.0593	0.132*	0.711 (4)
H18B	0.1135	0.2042	−0.0269	0.132*	0.711 (4)
H18C	0.2940	0.1256	−0.0604	0.132*	0.711 (4)
C19A	0.6141 (5)	0.2536 (4)	0.0647 (3)	0.0893 (11)	0.711 (4)
H19A	0.6306	0.1656	0.0255	0.134*	0.711 (4)
H19B	0.6857	0.2605	0.1257	0.134*	0.711 (4)
H19C	0.6752	0.3392	0.0381	0.134*	0.711 (4)
C20A	0.2862 (7)	0.1213 (3)	0.1233 (2)	0.0839 (10)	0.711 (4)
H20A	0.1356	0.1128	0.1267	0.126*	0.711 (4)
H20B	0.3579	0.1406	0.1852	0.126*	0.711 (4)
H20C	0.3098	0.0303	0.0902	0.126*	0.711 (4)
C18B	0.392 (4)	0.266 (2)	−0.0247 (12)	0.0881 (11)	0.144 (4)
H18D	0.5084	0.3477	−0.0275	0.132*	0.144 (4)
H18E	0.2615	0.2846	−0.0508	0.132*	0.144 (4)
H18F	0.4180	0.1769	−0.0597	0.132*	0.144 (4)
C19B	0.554 (3)	0.190 (2)	0.1180 (13)	0.0893 (11)	0.144 (4)
H19D	0.5548	0.0926	0.0857	0.134*	0.144 (4)
H19E	0.5330	0.1849	0.1823	0.134*	0.144 (4)
H19F	0.6884	0.2563	0.1144	0.134*	0.144 (4)
C20B	0.154 (3)	0.1210 (15)	0.0767 (14)	0.0839 (10)	0.144 (4)
H20D	0.0333	0.1525	0.0515	0.126*	0.144 (4)
H20E	0.1378	0.1083	0.1403	0.126*	0.144 (4)
H20F	0.1639	0.0284	0.0406	0.126*	0.144 (4)
C18C	0.512 (3)	0.2889 (16)	0.0029 (10)	0.0881 (11)	0.146 (3)
H18G	0.6459	0.3494	0.0330	0.132*	0.146 (3)
H18H	0.4467	0.3441	−0.0364	0.132*	0.146 (3)
H18I	0.5370	0.2016	−0.0342	0.132*	0.146 (3)
C19C	0.465 (3)	0.1613 (18)	0.1414 (11)	0.0893 (11)	0.146 (3)
H19G	0.4762	0.0664	0.1090	0.134*	0.146 (3)
H19H	0.3729	0.1470	0.1902	0.134*	0.146 (3)
H19I	0.6045	0.2170	0.1681	0.134*	0.146 (3)
C20C	0.151 (3)	0.1494 (14)	0.0290 (12)	0.0839 (10)	0.146 (3)
H20G	0.0924	0.1971	−0.0174	0.126*	0.146 (3)
H20H	0.0553	0.1377	0.0769	0.126*	0.146 (3)
H20I	0.1671	0.0537	0.0004	0.126*	0.146 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0675 (7)	0.0415 (5)	0.0719 (7)	0.0107 (5)	0.0124 (5)	−0.0031 (5)
C14	0.0553 (8)	0.0396 (7)	0.0530 (8)	0.0100 (6)	0.0031 (6)	0.0018 (6)
O3	0.0669 (7)	0.0466 (6)	0.0872 (8)	0.0212 (5)	−0.0081 (6)	−0.0158 (5)
O2	0.0765 (8)	0.0623 (7)	0.0795 (8)	0.0150 (6)	0.0226 (6)	−0.0061 (6)
C4	0.0596 (9)	0.0490 (8)	0.0510 (8)	0.0159 (6)	0.0010 (6)	0.0033 (6)
C12	0.0680 (10)	0.0546 (9)	0.0662 (10)	0.0222 (7)	−0.0162 (8)	−0.0138 (7)
O4	0.0957 (10)	0.0718 (8)	0.0843 (9)	0.0461 (7)	−0.0186 (7)	−0.0141 (7)
C5	0.0616 (9)	0.0469 (8)	0.0546 (8)	0.0136 (6)	0.0032 (7)	0.0064 (6)
C11	0.0569 (8)	0.0403 (7)	0.0510 (8)	0.0121 (6)	0.0050 (6)	0.0031 (6)
C16	0.0559 (9)	0.0595 (9)	0.0694 (10)	0.0220 (7)	−0.0057 (7)	−0.0043 (8)
C13	0.0699 (10)	0.0575 (9)	0.0706 (11)	0.0294 (8)	−0.0168 (8)	−0.0114 (8)
C2	0.0608 (9)	0.0419 (7)	0.0707 (10)	0.0101 (6)	0.0048 (7)	0.0005 (7)
C10	0.0614 (9)	0.0450 (7)	0.0553 (8)	0.0173 (6)	0.0038 (7)	0.0032 (6)
C17	0.0630 (9)	0.0433 (7)	0.0565 (9)	0.0141 (6)	0.0046 (7)	−0.0024 (6)
C15	0.0551 (9)	0.0557 (9)	0.0695 (10)	0.0136 (7)	−0.0081 (7)	−0.0111 (7)
C6	0.0731 (11)	0.0516 (9)	0.0747 (11)	0.0062 (8)	0.0028 (9)	0.0102 (8)
C3	0.0611 (9)	0.0405 (7)	0.0608 (9)	0.0165 (6)	−0.0026 (7)	−0.0036 (6)
C9	0.0693 (10)	0.0744 (11)	0.0607 (10)	0.0247 (9)	0.0060 (8)	−0.0002 (8)
C1	0.0621 (9)	0.0469 (8)	0.0610 (9)	0.0134 (7)	0.0050 (7)	0.0001 (7)
C8	0.0673 (11)	0.1024 (16)	0.0702 (12)	0.0151 (10)	0.0156 (9)	0.0135 (11)
C7	0.0711 (11)	0.0790 (13)	0.0798 (12)	0.0017 (9)	0.0084 (9)	0.0219 (10)
C18A	0.122 (3)	0.077 (2)	0.0622 (15)	0.044 (2)	−0.0175 (19)	−0.0209 (14)
C19A	0.0668 (16)	0.084 (2)	0.106 (3)	0.0231 (15)	0.0170 (16)	−0.0296 (18)
C20A	0.125 (3)	0.0432 (11)	0.086 (2)	0.0221 (15)	0.0319 (19)	0.0047 (13)
C18B	0.122 (3)	0.077 (2)	0.0622 (15)	0.044 (2)	−0.0175 (19)	−0.0209 (14)
C19B	0.0668 (16)	0.084 (2)	0.106 (3)	0.0231 (15)	0.0170 (16)	−0.0296 (18)
C20B	0.125 (3)	0.0432 (11)	0.086 (2)	0.0221 (15)	0.0319 (19)	0.0047 (13)
C18C	0.122 (3)	0.077 (2)	0.0622 (15)	0.044 (2)	−0.0175 (19)	−0.0209 (14)
C19C	0.0668 (16)	0.084 (2)	0.106 (3)	0.0231 (15)	0.0170 (16)	−0.0296 (18)
C20C	0.125 (3)	0.0432 (11)	0.086 (2)	0.0221 (15)	0.0319 (19)	0.0047 (13)

Geometric parameters (Å, º) top

O1—C1	1.374 (2)	C6—C7	1.369 (3)
O1—C5	1.3760 (19)	C6—H6	0.9300
C14—C15	1.380 (2)	C9—C8	1.375 (3)
C14—C13	1.380 (2)	C9—H9	0.9300
C14—C17	1.5322 (19)	C8—C7	1.385 (3)
O3—C10	1.3691 (19)	C8—H8	0.9300
O3—C3	1.3883 (17)	C7—H7	0.9300
O2—C1	1.2048 (19)	C18A—H18A	0.9600
C4—C5	1.395 (2)	C18A—H18B	0.9600
C4—C9	1.398 (2)	C18A—H18C	0.9600
C4—C3	1.435 (2)	C19A—H19A	0.9600
C12—C11	1.376 (2)	C19A—H19B	0.9600
C12—C13	1.390 (2)	C19A—H19C	0.9600
C12—H12	0.9300	C20A—H20A	0.9600
O4—C10	1.1906 (18)	C20A—H20B	0.9600
C5—C6	1.380 (2)	C20A—H20C	0.9600
C11—C16	1.380 (2)	C18B—H18D	0.9600
C11—C10	1.4792 (19)	C18B—H18E	0.9600
C16—C15	1.383 (2)	C18B—H18F	0.9600
C16—H16	0.9300	C19B—H19D	0.9600
C13—H13	0.9300	C19B—H19E	0.9600
C2—C3	1.331 (2)	C19B—H19F	0.9600
C2—C1	1.444 (2)	C20B—H20D	0.9600
C2—H2	0.9300	C20B—H20E	0.9600
C17—C18C	1.442 (16)	C20B—H20F	0.9600
C17—C18B	1.465 (17)	C18C—H18G	0.9600
C17—C20A	1.498 (3)	C18C—H18H	0.9600
C17—C19C	1.533 (17)	C18C—H18I	0.9600
C17—C19B	1.533 (16)	C19C—H19G	0.9600
C17—C18A	1.538 (3)	C19C—H19H	0.9600
C17—C19A	1.554 (3)	C19C—H19I	0.9600
C17—C20C	1.557 (16)	C20C—H20G	0.9600
C17—C20B	1.634 (17)	C20C—H20H	0.9600
C15—H15	0.9300	C20C—H20I	0.9600

C1—O1—C5	122.13 (12)	C14—C17—C20B	106.5 (5)
C15—C14—C13	116.78 (13)	C19C—C17—C20B	82.4 (9)
C15—C14—C17	121.34 (13)	C19B—C17—C20B	105.6 (8)
C13—C14—C17	121.88 (13)	C18A—C17—C20B	76.5 (7)
C10—O3—C3	119.42 (12)	C19A—C17—C20B	138.2 (6)
C5—C4—C9	118.27 (15)	C14—C15—C16	121.97 (14)
C5—C4—C3	116.26 (14)	C14—C15—H15	119.0
C9—C4—C3	125.47 (15)	C16—C15—H15	119.0
C11—C12—C13	119.84 (14)	C7—C6—C5	118.66 (17)
C11—C12—H12	120.1	C7—C6—H6	120.7
C13—C12—H12	120.1	C5—C6—H6	120.7
O1—C5—C6	116.91 (14)	C2—C3—O3	122.37 (15)
O1—C5—C4	121.30 (14)	C2—C3—C4	122.51 (14)
C6—C5—C4	121.79 (16)	O3—C3—C4	115.05 (14)
C12—C11—C16	118.93 (13)	C8—C9—C4	119.91 (18)
C12—C11—C10	123.52 (14)	C8—C9—H9	120.0
C16—C11—C10	117.54 (13)	C4—C9—H9	120.0
C11—C16—C15	120.26 (14)	O2—C1—O1	116.63 (14)
C11—C16—H16	119.9	O2—C1—C2	126.09 (16)
C15—C16—H16	119.9	O1—C1—C2	117.28 (14)
C14—C13—C12	122.17 (14)	C9—C8—C7	120.33 (18)
C14—C13—H13	118.9	C9—C8—H8	119.8
C12—C13—H13	118.9	C7—C8—H8	119.8
C3—C2—C1	120.32 (15)	C6—C7—C8	121.00 (18)
C3—C2—H2	119.8	C6—C7—H7	119.5
C1—C2—H2	119.8	C8—C7—H7	119.5
O4—C10—O3	122.60 (14)	C17—C18A—H18A	109.5
O4—C10—C11	126.25 (15)	C17—C18A—H18B	109.5
O3—C10—C11	111.12 (12)	C17—C18A—H18C	109.5
C18C—C17—C20A	143.4 (6)	C17—C19A—H19A	109.5
C18B—C17—C20A	136.4 (7)	C17—C19A—H19B	109.5
C18C—C17—C14	105.8 (5)	C17—C19A—H19C	109.5
C18B—C17—C14	108.4 (6)	C17—C20A—H20A	109.5
C20A—C17—C14	109.06 (15)	C17—C20A—H20B	109.5
C18C—C17—C19C	113.7 (8)	C17—C20A—H20C	109.5
C18B—C17—C19C	136.7 (8)	C17—C18B—H18D	109.5
C14—C17—C19C	108.2 (5)	C17—C18B—H18E	109.5
C18C—C17—C19B	87.6 (9)	H18D—C18B—H18E	109.5
C18B—C17—C19B	114.8 (8)	C17—C18B—H18F	109.5
C20A—C17—C19B	69.0 (8)	H18D—C18B—H18F	109.5
C14—C17—C19B	112.8 (5)	H18E—C18B—H18F	109.5
C18C—C17—C18A	64.7 (7)	C17—C19B—H19D	109.5
C20A—C17—C18A	110.4 (2)	C17—C19B—H19E	109.5
C14—C17—C18A	112.45 (16)	H19D—C19B—H19E	109.5
C19C—C17—C18A	138.0 (5)	C17—C19B—H19F	109.5
C19B—C17—C18A	131.7 (6)	H19D—C19B—H19F	109.5
C18C—C17—C19A	47.3 (7)	H19E—C19B—H19F	109.5
C18B—C17—C19A	78.1 (9)	C17—C20B—H20D	109.5
C20A—C17—C19A	108.4 (2)	C17—C20B—H20E	109.5
C14—C17—C19A	110.35 (15)	H20D—C20B—H20E	109.5
C19C—C17—C19A	67.9 (7)	C17—C20B—H20F	109.5
C18A—C17—C19A	106.2 (2)	H20D—C20B—H20F	109.5
C18C—C17—C20C	112.4 (7)	H20E—C20B—H20F	109.5
C18B—C17—C20C	81.3 (9)	C17—C18C—H18G	109.5
C20A—C17—C20C	65.9 (6)	C17—C18C—H18H	109.5
C14—C17—C20C	109.1 (5)	C17—C18C—H18I	109.5
C19C—C17—C20C	107.5 (7)	C17—C19C—H19G	109.5
C19B—C17—C20C	125.8 (8)	C17—C19C—H19H	109.5
C18A—C17—C20C	48.9 (7)	C17—C19C—H19I	109.5
C19A—C17—C20C	139.5 (5)	C17—C20C—H20G	109.5
C18C—C17—C20B	136.6 (8)	C17—C20C—H20H	109.5
C18B—C17—C20B	108.4 (8)	C17—C20C—H20I	109.5

C1—O1—C5—C6	−179.82 (15)	C13—C14—C17—C18A	−152.6 (2)
C1—O1—C5—C4	0.4 (2)	C15—C14—C17—C19A	146.2 (2)
C9—C4—C5—O1	−177.87 (14)	C13—C14—C17—C19A	−34.3 (3)
C3—C4—C5—O1	2.9 (2)	C15—C14—C17—C20C	−24.5 (7)
C9—C4—C5—C6	2.4 (2)	C13—C14—C17—C20C	155.0 (7)
C3—C4—C5—C6	−176.80 (15)	C15—C14—C17—C20B	−54.0 (9)
C13—C12—C11—C16	1.2 (3)	C13—C14—C17—C20B	125.5 (9)
C13—C12—C11—C10	−177.33 (16)	C13—C14—C15—C16	1.4 (3)
C12—C11—C16—C15	−2.0 (3)	C17—C14—C15—C16	−179.10 (16)
C10—C11—C16—C15	176.59 (16)	C11—C16—C15—C14	0.7 (3)
C15—C14—C13—C12	−2.2 (3)	O1—C5—C6—C7	178.80 (16)
C17—C14—C13—C12	178.25 (17)	C4—C5—C6—C7	−1.4 (3)
C11—C12—C13—C14	1.0 (3)	C1—C2—C3—O3	175.81 (15)
C3—O3—C10—O4	−0.7 (3)	C1—C2—C3—C4	−0.9 (3)
C3—O3—C10—C11	177.51 (14)	C10—O3—C3—C2	60.6 (2)
C12—C11—C10—O4	179.64 (18)	C10—O3—C3—C4	−122.45 (16)
C16—C11—C10—O4	1.1 (3)	C5—C4—C3—C2	−2.7 (2)
C12—C11—C10—O3	1.5 (2)	C9—C4—C3—C2	178.21 (16)
C16—C11—C10—O3	−177.09 (14)	C5—C4—C3—O3	−179.61 (13)
C15—C14—C17—C18C	96.6 (8)	C9—C4—C3—O3	1.3 (2)
C13—C14—C17—C18C	−83.9 (8)	C5—C4—C9—C8	−1.4 (3)
C15—C14—C17—C18B	62.4 (10)	C3—C4—C9—C8	177.69 (17)
C13—C14—C17—C18B	−118.1 (10)	C5—O1—C1—O2	175.72 (14)
C15—C14—C17—C20A	−94.8 (2)	C5—O1—C1—C2	−4.0 (2)
C13—C14—C17—C20A	84.7 (3)	C3—C2—C1—O2	−175.46 (17)
C15—C14—C17—C19C	−141.2 (7)	C3—C2—C1—O1	4.2 (2)
C13—C14—C17—C19C	38.2 (8)	C4—C9—C8—C7	−0.4 (3)
C15—C14—C17—C19B	−169.4 (10)	C5—C6—C7—C8	−0.5 (3)
C13—C14—C17—C19B	10.1 (10)	C9—C8—C7—C6	1.4 (3)
C15—C14—C17—C18A	27.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.93	2.39	3.323 (2)	177
C18B—H18D···Cg3ⁱⁱ	0.96	2.83	3.54 (2)	133
C18C—H18I···Cg3ⁱⁱ	0.96	2.90	3.47 (2)	119
C19C—H19I···Cg2ⁱⁱⁱ	0.96	2.95	3.75 (2)	141
C1—O2···Cg2^iv	1.21 (1)	3.53 (1)	3.802 (2)	95 (1)

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈O₄
M_r	322.34
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.4319 (2), 9.3498 (3), 14.5505 (5)
α, β, γ (°)	98.481 (1), 93.655 (1), 102.359 (2)
V (Å³)	841.27 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.30 × 0.14

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11164, 4198, 2926
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.683

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.157, 1.05
No. of reflections	4198
No. of parameters	247
No. of restraints	10
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16

Computer programs: COLLECT (Hooft, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR2004 (Burla et al., 2005), PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008), publCIF (Westrip, 2010) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.93	2.39	3.323 (2)	177
C18B—H18D···Cg3ⁱⁱ	0.96	2.83	3.54 (2)	133
C18C—H18I···Cg3ⁱⁱ	0.96	2.90	3.47 (2)	119
C19C—H19I···Cg2ⁱⁱⁱ	0.96	2.95	3.75 (2)	141

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

Acknowledgements

We thank the Laboratoire de Physique des Interactions Ioniques et Moléculaires (Université de Provence), and Spectropôle (Université Paul Cézanne, Faculté des Sciences et Techniques de Saint Jérôme, Marseille, France), for the use of the diffractometer.

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