1,4-Di-tert-butyl (2R,3R)-2-({(2E)-3-[4-(acet­yloxy)phen­yl]prop-2-eno­yl}­oxy)-3-hy­droxy­butane­dioate

Hixson, J.L.; Taylor, D.K.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S160053681200236X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o509-o510

doi:10.1107/S160053681200236X

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1,4-Di-tert-butyl (2R,3R)-2-({(2E)-3-[4-(acetyloxy)phenyl]prop-2-enoyl}oxy)-3-hydroxybutanedioate

Josh L. Hixson,^a Dennis K. Taylor,^a ‡ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aSchool of Agriculture, Food and Wine, The University of Adelaide, Waite Campus, PMB 1, Glen Osmond, SA 5064, Australia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 18 January 2012; accepted 18 January 2012; online 25 January 2012)

The title compound, C₂₃H₃₀O₉, has an approximate T-shape with the tert-butyl ester groups lying either side of the benzene ring. The acetyl group is almost perpendicular to the benzene ring to which it is connected [C—C—O—C torsion angle = −106.7 (3)°]. The conformation about the C=C double bond [1.331 (4) Å] is E. Linear supramolecular chains along the a axis mediated by hydroxy–carbonyl O—H⋯O hydrogen bonds feature in the crystal packing. The same H atom is also involved in an intramolecular O—H⋯O interaction.

Related literature

For background to the formation of the odorant 4-ethylphenol with relevance to the wine industry, see: Chatonnet et al. (1992 ); Hixson et al. (2012 ); Ong & Nagel (1978 ); Nagel & Wulf (1979 ); Zhao & Burke (1998 ). For the preparation and characterization of 1-O-acetyl p-coumaric acid; see: Zhao & Burke (1998); Shimizu & Kojima (1984 ).

Experimental

Crystal data

C₂₃H₃₀O₉
M_r = 450.47
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.7183 (2) Å
b = 8.7309 (3) Å
c = 46.9988 (19) Å
V = 2346.46 (15) Å³
Z = 4
Cu Kα radiation
μ = 0.82 mm⁻¹
T = 100 K
0.35 × 0.10 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.230, T_max = 1.000
9078 measured reflections
4603 independent reflections
3842 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.131
S = 1.05
4603 reflections
300 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ), 1849 Friedel pairs
Flack parameter: 0.0 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O16—H16⋯O27ⁱ	0.85 (4)	2.06 (4)	2.842 (3)	153 (4)
O16—H16⋯O30	0.85 (4)	2.26 (4)	2.688 (3)	111 (3)
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681200236X/hb6610sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200236X/hb6610Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681200236X/hb6610Isup3.cml

checkCIF report

Comment top

The breakdown of p-coumaric acid by D. bruxellensis to form the potent odorant 4-ethylphenol has been known for decades (Chatonnet et al., 1992). Recently, it has been found that the metabolism of the ethyl ester of p-coumaric acid by this yeast can also result in the accumulation of significant concentrations of 4-ethylphenol (Hixson et al., 2012). Existing in both the grape berry and in wine in significant concentrations (Ong & Nagel, 1978; Nagel & Wulf, 1979), the p-coumaroyl L-tartrate ester has the potential to contribute even further to the accumulation of 4-ethylphenol in finished wines and thus contribute further to the spoilage of wine.

Synthesis of the known wine component p-coumaroyl L-tartrate was attempted using di-tert-butyl L-tartrate and the 1-O-acetyl protected hydroxycinnamic acid in an analogous method to that described by Zhao and Burke (1998). The desired product was isolated and recrystallized from 30% ethyl acetate/hexane to afford a crystalline solid from which the structure was determined by X-ray crystallography to confirm the retention of the (R,R)-stereochemistry, Fig. 1.

The most prominent feature of the crystal packing is the formation of linear supramolecular chains along the a axis via hydroxyl-O—H···O(carbonyl) hydrogen bonds, Fig. 2 and Table 1. The hydroxyl-H atom is bifurcated, also forming an intramolecular O–H···O hydrogen bond with the adjacent carbonyl-O atom, Table 1.

Related literature top

For background to the formation of the odorant 4-ethylphenol with relevance to the wine industry, see: Chatonnet et al. (1992); Hixson et al. (2012); Ong & Nagel (1978); Nagel & Wulf (1979); Zhao & Burke (1998). For the preparation and characterization of 1-O-acetyl p-coumaric acid; see: Zhao & Burke (1998); Shimizu & Kojima (1984).

Experimental top

1-O-Acetyl p-coumaric acid was prepared using a method analogous to that previously described by Zhao and Burke (1998), and the characterization data matched that previously described (Shimizu & Kojima, 1984). 1-O-Acetyl p-coumaric acid (0.17 g 0.82 mmol) was heated under reflux in dry benzene (10 ml) containing thionyl chloride (1 ml, 13.77 mmol). After 5 h the mixture was allowed to cool to room temperature and then concentrated in vacuo. The crude residue was taken up in dry benzene (3 ml) and added drop-wise to a solution of di-tert-butyl L-tartrate (0.13 g, 0.49 mmol) in dry pyridine (3 ml), then stirred at ambient temperature overnight. The mixture was concentrated and pyridine azeotropically removed with toluene. Purification with column chromatography (20% EtOAc/X4) and recrystallization from 30% EtOAc/X4 gave 68.1 mg (31%) of colourless plates. M.pt 416.8–417.4 K. R_f (50% EtOAc/X4): 0.57 ¹H NMR: (400 MHz, CDCl₃) δ: 7.73 (d, 1H, J = 16.0 Hz, H₇), 7.54 (app. d, 2H, J = 8.7 Hz, H_3,5), 7.13 (app. d, 2H, J = 8.7 Hz, H_2,6), 6.45 (d, 1H, J = 16.0 Hz, H₈), 5.48 (d, 1H, J = 2.3 Hz, H_2'), 4.67 (dd, 1H, J = 6.9 and 2.3 Hz, H_3'), 3.20 (d, 1H, J = 6.9 Hz, OH), 2.31 (s, 3H, OCOCH₃), 1.51 (s, 9H, ^tBu₄), 1.44 (s, 9H, ^tBu₁). ¹³C NMR: (600 MHz, CDCl₃) δ: 170.2 (C4'), 169.3 (OCOCH₃), 165.8 (C9), 165.5 (C1'), 152.4 (C1), 145.5 (C7), 131.9 (C4), 129.6 (C3,5), 122.3 (C2,6), 116.7 (C8), 84.0 (C₁(CH₃)₃), 83.4 (C₄(CH₃)₃), 73.5 (C2'), 71.0 (C3'), 28.1 (C₄(CH₃)₃), 28.0 (C1(CH₃)₃), 21.3 (OCOCH₃). LRP (+EI) m/z (%): 450 (M+, <1), 408 (2), 352 (10), 338 (5), 321 (12), 296 (63), 278 (6), 251 (6), 206 (7), 189 (46), 164 (79), 147 (100), 119 (14), 57 (37), 41 (13). HRMS calculated for C₂₃H₃₀O₉ [M]+ 450.1890, found 450.1891.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The asymmetric unit of (I) showing displacement ellipsoids at the 70% probability level.
	Fig. 2. A view of the linear supramolecular chain along the a axis mediated by O—H···O hydrogen bonds shown as orange dashed lines.

1,4-Di-tert-butyl (2R,3R)-2-({(2E)- 3-[4-(acetyloxy)phenyl]prop-2-enoyl}oxy)-3-hydroxybutanedioate top

Crystal data top

C₂₃H₃₀O₉	F(000) = 960
M_r = 450.47	D_x = 1.275 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2558 reflections
a = 5.7183 (2) Å	θ = 2.8–74.4°
b = 8.7309 (3) Å	µ = 0.82 mm⁻¹
c = 46.9988 (19) Å	T = 100 K
V = 2346.46 (15) Å³	Plate, colourless
Z = 4	0.35 × 0.10 × 0.02 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4603 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3842 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.044
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.6°, θ_min = 3.8°
ω scan	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −10→7
T_min = 0.230, T_max = 1.000	l = −56→58
9078 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0669P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4603 reflections	Δρ_max = 0.28 e Å⁻³
300 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1849 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.0 (2)

Crystal data top

C₂₃H₃₀O₉	V = 2346.46 (15) Å³
M_r = 450.47	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 5.7183 (2) Å	µ = 0.82 mm⁻¹
b = 8.7309 (3) Å	T = 100 K
c = 46.9988 (19) Å	0.35 × 0.10 × 0.02 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4603 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3842 reflections with I > 2σ(I)
T_min = 0.230, T_max = 1.000	R_int = 0.044
9078 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.131	Δρ_max = 0.28 e Å⁻³
S = 1.05	Δρ_min = −0.30 e Å⁻³
4603 reflections	Absolute structure: Flack (1983), 1849 Friedel pairs
300 parameters	Absolute structure parameter: 0.0 (2)
0 restraints

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O7	−0.2022 (4)	0.5527 (2)	−0.00826 (4)	0.0253 (5)
O9	−0.3426 (4)	0.3380 (2)	0.01232 (4)	0.0263 (4)
O13	0.3891 (3)	0.9744 (2)	0.14782 (4)	0.0188 (4)
O16	0.2916 (4)	1.1953 (2)	0.19343 (5)	0.0239 (4)
H16	0.147 (7)	1.178 (5)	0.1910 (8)	0.042 (11)*
O18	0.6765 (4)	0.8572 (2)	0.12326 (4)	0.0238 (4)
O20	0.6536 (3)	1.2024 (2)	0.13224 (4)	0.0198 (4)
O24	0.3937 (3)	0.8007 (2)	0.20890 (4)	0.0201 (4)
O27	0.8203 (3)	1.2333 (2)	0.17558 (4)	0.0239 (4)
O30	0.0551 (4)	0.9341 (2)	0.20280 (4)	0.0237 (5)
C1	−0.0842 (5)	0.5915 (3)	0.01690 (6)	0.0223 (6)
C2	−0.1778 (5)	0.7016 (3)	0.03504 (6)	0.0225 (6)
H2	−0.3271	0.7450	0.0314	0.027*
C3	−0.0493 (5)	0.7466 (3)	0.05852 (6)	0.0206 (6)
H3	−0.1120	0.8210	0.0711	0.025*
C4	0.1717 (5)	0.6843 (3)	0.06398 (6)	0.0199 (6)
C5	0.2585 (5)	0.5716 (3)	0.04550 (6)	0.0211 (6)
H5	0.4074	0.5272	0.0490	0.025*
C6	0.1294 (5)	0.5244 (3)	0.02212 (6)	0.0230 (6)
H6	0.1876	0.4467	0.0099	0.028*
C8	−0.3134 (5)	0.4121 (3)	−0.00867 (6)	0.0221 (6)
C10	0.3277 (5)	0.7401 (3)	0.08639 (6)	0.0211 (6)
H10	0.4826	0.7008	0.0861	0.025*
C11	0.2799 (5)	0.8390 (3)	0.10715 (6)	0.0203 (6)
H11	0.1259	0.8775	0.1098	0.024*
C12	0.4738 (5)	0.8874 (3)	0.12611 (6)	0.0185 (6)
C14	0.5580 (5)	1.0245 (3)	0.16863 (6)	0.0167 (5)
H14	0.6722	0.9400	0.1723	0.020*
C15	0.4241 (5)	1.0593 (3)	0.19588 (6)	0.0183 (6)
H15	0.5391	1.0723	0.2117	0.022*
C17	−0.3823 (7)	0.3715 (3)	−0.03830 (7)	0.0339 (8)
H17A	−0.5229	0.3073	−0.0379	0.051*
H17B	−0.2546	0.3151	−0.0475	0.051*
H17C	−0.4146	0.4652	−0.0491	0.051*
C19	0.6905 (5)	1.1681 (3)	0.15925 (6)	0.0178 (5)
C21	0.7821 (5)	1.3308 (3)	0.11844 (6)	0.0223 (6)
C22	0.6898 (6)	1.3215 (4)	0.08806 (6)	0.0286 (6)
H22A	0.5236	1.3489	0.0878	0.043*
H22B	0.7091	1.2169	0.0809	0.043*
H22C	0.7772	1.3927	0.0760	0.043*
C23	0.2640 (5)	0.9244 (3)	0.20304 (6)	0.0174 (6)
C25	0.2773 (5)	0.6517 (3)	0.21600 (6)	0.0231 (6)
C26	0.4859 (5)	0.5481 (3)	0.22185 (7)	0.0296 (7)
H26A	0.5811	0.5391	0.2046	0.044*
H26B	0.4304	0.4464	0.2275	0.044*
H26C	0.5806	0.5921	0.2372	0.044*
C28	1.0416 (5)	1.3012 (4)	0.11923 (7)	0.0325 (7)
H28A	1.0969	1.3064	0.1389	0.049*
H28B	1.1226	1.3787	0.1078	0.049*
H28C	1.0741	1.1992	0.1115	0.049*
C29	0.7116 (6)	1.4816 (3)	0.13230 (7)	0.0274 (7)
H29A	0.7685	1.4839	0.1520	0.041*
H29B	0.5408	1.4908	0.1322	0.041*
H29C	0.7801	1.5670	0.1216	0.041*
C30	0.1389 (6)	0.5973 (4)	0.19021 (7)	0.0311 (7)
H30A	0.2419	0.5935	0.1736	0.047*
H30B	0.0099	0.6686	0.1865	0.047*
H30C	0.0757	0.4949	0.1939	0.047*
C31	0.1284 (5)	0.6724 (4)	0.24249 (7)	0.0296 (7)
H31A	0.2228	0.7195	0.2576	0.044*
H31B	0.0714	0.5724	0.2489	0.044*
H31C	−0.0049	0.7388	0.2381	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O7	0.0322 (11)	0.0166 (9)	0.0271 (11)	−0.0050 (9)	−0.0090 (9)	−0.0005 (8)
O9	0.0275 (11)	0.0233 (10)	0.0280 (11)	−0.0045 (9)	−0.0019 (9)	−0.0005 (8)
O13	0.0177 (9)	0.0169 (9)	0.0217 (10)	−0.0009 (8)	−0.0013 (8)	−0.0032 (7)
O16	0.0225 (11)	0.0137 (9)	0.0356 (12)	0.0024 (9)	0.0004 (9)	−0.0015 (8)
O18	0.0204 (11)	0.0193 (9)	0.0318 (11)	0.0008 (8)	−0.0023 (9)	−0.0052 (8)
O20	0.0217 (10)	0.0151 (9)	0.0226 (10)	−0.0043 (8)	0.0012 (8)	0.0019 (7)
O24	0.0179 (9)	0.0131 (9)	0.0293 (11)	−0.0016 (8)	0.0003 (8)	0.0048 (7)
O27	0.0244 (11)	0.0183 (9)	0.0290 (11)	−0.0032 (8)	−0.0056 (9)	0.0016 (8)
O30	0.0233 (11)	0.0180 (10)	0.0299 (12)	0.0001 (8)	0.0004 (9)	0.0000 (8)
C1	0.0289 (15)	0.0154 (12)	0.0225 (15)	−0.0040 (12)	−0.0026 (13)	0.0023 (11)
C2	0.0227 (14)	0.0180 (12)	0.0268 (14)	−0.0017 (12)	−0.0005 (12)	0.0021 (11)
C3	0.0221 (14)	0.0155 (12)	0.0242 (15)	−0.0023 (11)	0.0019 (11)	−0.0016 (11)
C4	0.0204 (14)	0.0167 (12)	0.0225 (13)	−0.0026 (11)	0.0012 (11)	0.0010 (10)
C5	0.0228 (14)	0.0158 (12)	0.0248 (14)	−0.0008 (11)	0.0022 (11)	0.0000 (10)
C6	0.0297 (16)	0.0175 (12)	0.0217 (14)	−0.0003 (12)	0.0018 (12)	−0.0023 (10)
C8	0.0221 (14)	0.0163 (12)	0.0277 (15)	0.0015 (11)	−0.0015 (13)	−0.0033 (11)
C10	0.0188 (14)	0.0196 (13)	0.0248 (14)	−0.0014 (11)	−0.0008 (12)	0.0012 (10)
C11	0.0187 (13)	0.0184 (13)	0.0238 (14)	−0.0015 (11)	−0.0008 (11)	−0.0007 (10)
C12	0.0197 (15)	0.0115 (12)	0.0242 (15)	−0.0023 (10)	0.0004 (11)	−0.0006 (10)
C14	0.0165 (13)	0.0119 (11)	0.0217 (14)	−0.0020 (10)	−0.0026 (11)	0.0007 (10)
C15	0.0206 (13)	0.0125 (12)	0.0218 (14)	0.0001 (11)	−0.0021 (11)	0.0002 (10)
C17	0.048 (2)	0.0223 (14)	0.0309 (17)	−0.0038 (14)	−0.0075 (16)	−0.0023 (13)
C19	0.0158 (13)	0.0135 (12)	0.0241 (14)	0.0003 (10)	−0.0005 (11)	0.0011 (10)
C21	0.0229 (14)	0.0152 (12)	0.0288 (15)	0.0001 (11)	0.0060 (12)	0.0056 (11)
C22	0.0310 (16)	0.0275 (15)	0.0274 (15)	0.0009 (13)	0.0054 (14)	0.0060 (12)
C23	0.0182 (14)	0.0176 (13)	0.0165 (13)	0.0003 (11)	−0.0006 (10)	−0.0006 (10)
C25	0.0247 (15)	0.0135 (12)	0.0311 (16)	−0.0033 (11)	−0.0002 (12)	0.0061 (11)
C26	0.0258 (15)	0.0207 (15)	0.042 (2)	0.0004 (12)	−0.0018 (13)	0.0086 (14)
C28	0.0271 (16)	0.0329 (17)	0.0375 (19)	0.0016 (14)	0.0079 (14)	0.0106 (15)
C29	0.0335 (17)	0.0134 (13)	0.0353 (17)	0.0033 (12)	−0.0024 (14)	0.0006 (11)
C30	0.0314 (17)	0.0219 (14)	0.0400 (18)	−0.0030 (13)	−0.0073 (14)	−0.0039 (13)
C31	0.0267 (16)	0.0272 (15)	0.0348 (16)	−0.0034 (13)	0.0022 (13)	0.0112 (13)

Geometric parameters (Å, º) top

O7—C8	1.383 (3)	C14—C19	1.530 (3)
O7—C1	1.403 (3)	C14—H14	1.0000
O9—C8	1.192 (3)	C15—C23	1.529 (4)
O13—C12	1.361 (3)	C15—H15	1.0000
O13—C14	1.442 (3)	C17—H17A	0.9800
O16—C15	1.414 (3)	C17—H17B	0.9800
O16—H16	0.85 (4)	C17—H17C	0.9800
O18—C12	1.196 (4)	C21—C28	1.507 (4)
O20—C19	1.321 (3)	C21—C29	1.523 (4)
O20—C21	1.489 (3)	C21—C22	1.524 (4)
O24—C23	1.339 (3)	C22—H22A	0.9800
O24—C25	1.499 (3)	C22—H22B	0.9800
O27—C19	1.210 (3)	C22—H22C	0.9800
O30—C23	1.198 (3)	C25—C31	1.519 (4)
C1—C6	1.377 (4)	C25—C26	1.522 (4)
C1—C2	1.392 (4)	C25—C30	1.523 (4)
C2—C3	1.383 (4)	C26—H26A	0.9800
C2—H2	0.9500	C26—H26B	0.9800
C3—C4	1.400 (4)	C26—H26C	0.9800
C3—H3	0.9500	C28—H28A	0.9800
C4—C5	1.403 (4)	C28—H28B	0.9800
C4—C10	1.464 (4)	C28—H28C	0.9800
C5—C6	1.387 (4)	C29—H29A	0.9800
C5—H5	0.9500	C29—H29B	0.9800
C6—H6	0.9500	C29—H29C	0.9800
C8—C17	1.490 (4)	C31—H31A	0.9800
C10—C11	1.331 (4)	C31—H31B	0.9800
C10—H10	0.9500	C31—H31C	0.9800
C11—C12	1.484 (4)	C30—H30A	0.9800
C11—H11	0.9500	C30—H30B	0.9800
C14—C15	1.523 (4)	C30—H30C	0.9800

C8—O7—C1	116.5 (2)	O27—C19—C14	120.4 (2)
C12—O13—C14	116.1 (2)	O20—C19—C14	112.6 (2)
C15—O16—H16	113 (3)	O20—C21—C28	110.3 (2)
C19—O20—C21	120.7 (2)	O20—C21—C29	109.5 (2)
C23—O24—C25	120.0 (2)	C28—C21—C29	113.5 (3)
C6—C1—C2	121.7 (3)	O20—C21—C22	101.4 (2)
C6—C1—O7	118.3 (3)	C28—C21—C22	110.8 (3)
C2—C1—O7	119.9 (3)	C29—C21—C22	110.8 (2)
C3—C2—C1	118.7 (3)	C21—C22—H22A	109.5
C3—C2—H2	120.6	C21—C22—H22B	109.5
C1—C2—H2	120.6	H22A—C22—H22B	109.5
C2—C3—C4	121.0 (3)	C21—C22—H22C	109.5
C2—C3—H3	119.5	H22A—C22—H22C	109.5
C4—C3—H3	119.5	H22B—C22—H22C	109.5
C3—C4—C5	118.6 (3)	O30—C23—O24	127.7 (3)
C3—C4—C10	123.6 (3)	O30—C23—C15	122.7 (3)
C5—C4—C10	117.6 (3)	O24—C23—C15	109.6 (2)
C6—C5—C4	120.7 (3)	O24—C25—C31	109.1 (2)
C6—C5—H5	119.6	O24—C25—C26	102.0 (2)
C4—C5—H5	119.6	C31—C25—C26	111.2 (2)
C1—C6—C5	119.2 (3)	O24—C25—C30	108.9 (2)
C1—C6—H6	120.4	C31—C25—C30	113.5 (3)
C5—C6—H6	120.4	C26—C25—C30	111.5 (3)
O9—C8—O7	122.3 (3)	C25—C26—H26A	109.5
O9—C8—C17	127.4 (3)	C25—C26—H26B	109.5
O7—C8—C17	110.2 (2)	H26A—C26—H26B	109.5
C11—C10—C4	128.2 (3)	C25—C26—H26C	109.5
C11—C10—H10	115.9	H26A—C26—H26C	109.5
C4—C10—H10	115.9	H26B—C26—H26C	109.5
C10—C11—C12	118.1 (3)	C21—C28—H28A	109.5
C10—C11—H11	120.9	C21—C28—H28B	109.5
C12—C11—H11	120.9	H28A—C28—H28B	109.5
O18—C12—O13	123.5 (3)	C21—C28—H28C	109.5
O18—C12—C11	126.5 (3)	H28A—C28—H28C	109.5
O13—C12—C11	110.1 (2)	H28B—C28—H28C	109.5
O13—C14—C15	107.1 (2)	C21—C29—H29A	109.5
O13—C14—C19	112.6 (2)	C21—C29—H29B	109.5
C15—C14—C19	109.2 (2)	H29A—C29—H29B	109.5
O13—C14—H14	109.3	C21—C29—H29C	109.5
C15—C14—H14	109.3	H29A—C29—H29C	109.5
C19—C14—H14	109.3	H29B—C29—H29C	109.5
O16—C15—C14	111.6 (2)	C25—C31—H31A	109.5
O16—C15—C23	110.2 (2)	C25—C31—H31B	109.5
C14—C15—C23	109.4 (2)	H31A—C31—H31B	109.5
O16—C15—H15	108.5	C25—C31—H31C	109.5
C14—C15—H15	108.5	H31A—C31—H31C	109.5
C23—C15—H15	108.5	H31B—C31—H31C	109.5
C8—C17—H17A	109.5	C25—C30—H30A	109.5
C8—C17—H17B	109.5	C25—C30—H30B	109.5
H17A—C17—H17B	109.5	H30A—C30—H30B	109.5
C8—C17—H17C	109.5	C25—C30—H30C	109.5
H17A—C17—H17C	109.5	H30A—C30—H30C	109.5
H17B—C17—H17C	109.5	H30B—C30—H30C	109.5
O27—C19—O20	126.9 (2)

C8—O7—C1—C6	76.9 (3)	O13—C14—C15—O16	−72.5 (3)
C8—O7—C1—C2	−106.7 (3)	C19—C14—C15—O16	49.7 (3)
C6—C1—C2—C3	1.5 (4)	O13—C14—C15—C23	49.7 (3)
O7—C1—C2—C3	−174.9 (3)	C19—C14—C15—C23	171.9 (2)
C1—C2—C3—C4	0.6 (4)	C21—O20—C19—O27	1.7 (4)
C2—C3—C4—C5	−1.7 (4)	C21—O20—C19—C14	−175.0 (2)
C2—C3—C4—C10	172.4 (3)	O13—C14—C19—O27	172.2 (2)
C3—C4—C5—C6	0.8 (4)	C15—C14—C19—O27	53.4 (3)
C10—C4—C5—C6	−173.6 (3)	O13—C14—C19—O20	−10.8 (3)
C2—C1—C6—C5	−2.3 (4)	C15—C14—C19—O20	−129.6 (2)
O7—C1—C6—C5	174.1 (2)	C19—O20—C21—C28	60.5 (3)
C4—C5—C6—C1	1.1 (4)	C19—O20—C21—C29	−65.0 (3)
C1—O7—C8—O9	12.1 (4)	C19—O20—C21—C22	177.9 (2)
C1—O7—C8—C17	−167.0 (3)	C25—O24—C23—O30	0.5 (4)
C3—C4—C10—C11	10.1 (5)	C25—O24—C23—C15	−178.7 (2)
C5—C4—C10—C11	−175.8 (3)	O16—C15—C23—O30	8.7 (4)
C4—C10—C11—C12	−175.2 (3)	C14—C15—C23—O30	−114.4 (3)
C14—O13—C12—O18	−2.7 (4)	O16—C15—C23—O24	−172.1 (2)
C14—O13—C12—C11	177.6 (2)	C14—C15—C23—O24	64.8 (3)
C10—C11—C12—O18	7.1 (4)	C23—O24—C25—C31	−60.6 (3)
C10—C11—C12—O13	−173.3 (2)	C23—O24—C25—C26	−178.3 (2)
C12—O13—C14—C15	−157.2 (2)	C23—O24—C25—C30	63.8 (3)
C12—O13—C14—C19	82.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O16—H16···O27ⁱ	0.85 (4)	2.06 (4)	2.842 (3)	153 (4)
O16—H16···O30	0.85 (4)	2.26 (4)	2.688 (3)	111 (3)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₃H₃₀O₉
M_r	450.47
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	5.7183 (2), 8.7309 (3), 46.9988 (19)
V (Å³)	2346.46 (15)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.82
Crystal size (mm)	0.35 × 0.10 × 0.02

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.230, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9078, 4603, 3842
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.131, 1.05
No. of reflections	4603
No. of parameters	300
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.30
Absolute structure	Flack (1983), 1849 Friedel pairs
Absolute structure parameter	0.0 (2)

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O16—H16···O27ⁱ	0.85 (4)	2.06 (4)	2.842 (3)	153 (4)
O16—H16···O30	0.85 (4)	2.26 (4)	2.688 (3)	111 (3)

Symmetry code: (i) x−1, y, z.

Footnotes

‡Additional correspondence author, e-mail: dennis.taylor@adelaide.edu.au.

Acknowledgements

This project was supported by the School of Agriculture, Food and Wine, the University of Adelaide, as well as by Australia's grape growers and winemakers through their investment body, the Grape and Wine Research and Development Corporation, with matching funds from the Australian Government. The Ministry of Higher Education (Malaysia) is thanked for funding structural studies through the High-Impact Research scheme (UM·C/HIR/MOHE/SC/12).

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Chatonnet, P., Dubourdieu, D., Boidron, J. N. & Pons, M. (1992). J. Sci. Food Agric. 60, 165–178. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hixson, J. L., Sleep, N. R., Capone, D. L., Elsey, G. M., Curtin, C. D., Sefton, M. A. & Taylor, D. K. (2012). J. Agric. Food Chem. Submitted. Google Scholar
Nagel, C. W. & Wulf, L. W. (1979). Am. J. Enol. Vitic. 30, 111–116. CAS Google Scholar
Ong, B. Y. & Nagel, C. W. (1978). Am. J. Enol. Vitic. 29, 277–281. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shimizu, T. & Kojima, M. (1984). J. Biochem. 95, 205–212. CAS PubMed Web of Science Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, H. & Burke, T. R. (1998). Synth. Commun. 28, 737–740. Web of Science CrossRef CAS Google Scholar

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Volume 68| Part 2| February 2012| Pages o509-o510

doi:10.1107/S160053681200236X

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

1,4-Di-tert-butyl (2R,3R)-2-({(2E)-3-[4-(acet­yl­oxy)phen­yl]prop-2-eno­yl}­­oxy)-3-hy­dr­oxy­butane­dioate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

1,4-Di-tert-butyl (2R,3R)-2-({(2E)-3-[4-(acetyloxy)phenyl]prop-2-enoyl}oxy)-3-hydroxybutanedioate