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

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

doi:10.1107/S1600536812002784

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o568-o569

doi:10.1107/S1600536812002784

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Di-tert-butyl (2R,3R)-2-{[(2E)-3-(4-acetyloxy-3-methoxyphenyl)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, 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 19 January 2012; accepted 22 January 2012; online 4 February 2012)

In the title molecule, C₂₄H₃₂O₁₀, one tert-butyl ester group is folded towards the central benzene ring while the other is directed away. The acetyl group is almost perpendicular to the benzene ring to which it is connected [C—C—O—C torsion angle = 90.4 (12)°]. The conformation about the ethene bond [1.313 (7) Å] is E. The atoms of the benzene ring and its attached ester group and part of the hydroxy tert-butyl ester side chain are disordered over two sets of sites in a 50:50 ratio. 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 also partakes in an intramolecular O—H⋯O interaction.

Related literature

For background to the formation of the odorant 4-ethylguaiacol 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 ferulic acid; see: Zhao & Burke (1998); Hosoda et al. (2001 ).

Experimental

Crystal data

C₂₄H₃₂O₁₀
M_r = 480.50
Monoclinic, P 2₁
a = 5.9894 (1) Å
b = 10.6483 (1) Å
c = 19.6676 (2) Å
β = 96.324 (1)°
V = 1246.71 (3) Å³
Z = 2
Cu Kα radiation
μ = 0.84 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.736, T_max = 1.000
7492 measured reflections
4800 independent reflections
4762 reflections with I > 2σ(I)
R_int = 0.011

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.159
S = 1.04
4800 reflections
326 parameters
113 restraints
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.56 e Å⁻³
Absolute structure: Flack (1983 ), 2185 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
O18—H18⋯O32	0.84	2.21	2.631 (8)	111
O18—H18⋯O22ⁱ	0.84	2.57	3.185 (5)	131
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/S1600536812002784/hb6612sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002784/hb6612Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812002784/hb6612Isup3.cml

checkCIF report

Comment top

The breakdown of ferulic acid by D. bruxellensis to form the potent odorant 4-ethylguaiacol has been known for decades (Chatonnet et al., 1992). Recently, it has been found that the metabolism of the ethyl ester of ferulic acid by this yeast can also result in the accumulation of 4-ethylguaiacol (Hixson et al., 2012). Existing in both the grape berry and in wine in significant concentrations (Ong & Nagel, 1978; Nagel & Wulf, 1979), the feruloyl L-tartrate ester has the potential to contribute to the accumulation of 4-ethylguaiacol in finished wines and thus contribute further to the spoilage of wine. Synthesis of the known wine component feruloyl L-tartrate was achieved using di-tert-butyl L-tartrate and the 1-O-acetyl protected hydroxycinnamic acid in an analogous method to that described by Zhao & Burke (1998). The products of coupling were 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 hydroxyl-H atom is bifurcated, forming an intramolecular O—H···O hydrogen bond with the adjacent carbonyl-O, Table, and an intermolecular O–H···O hydrogen bond with a translationally related carbonyl-O atom to form a linear supramolecular chain along the a axis, Fig. 1 and Table 1.

Related literature top

For background to the formation of the odorant 4-ethylguaiacol 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 ferulic acid; see: Zhao & Burke (1998); Hosoda et al. (2001).

Experimental top

1-O-Acetyl ferulic acid was prepared using a method analogous to that previously described by Zhao and Burke (1998), and the characterization data matched that previously described (Hosoda et al., 2001). 1-O-Acetyl ferulic acid (0.16 g, 0.67 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 (0.21 g, 0.79 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 154.0 mg (48%) of white crystals. M.pt 413.7–415.2 K. R_f (30% EtOAc/X4): 0.34 ¹H NMR: (600 MHz, CDCl₃) δ: 7.70 (d, 1H, J = 16.0 Hz, H₇), 7.12–7.11 (m, 2H, H_3,5), 7.05 (d, 1H, J = 8.6 Hz, H₆), 6.45 (d, 1H, J = 16.0 Hz, H₈), 5.50 (d, 1H, J = 2.3 Hz, H_2'), 4.68 (dd, 1H, J = 6.8 and 2.3 Hz, H_3'), 3.87 (s, 3H, OCH₃), 3.21 (d, 1H, J = 6.8 Hz, OH), 2.33 (s, 3H, OCOCH₃), 1.51 (s, 9H, t-Bu₄), 1.44 (s, 9H, ^tBu₁). ¹³C NMR: (600 MHz, CDCl₃) δ: 170.2 (C_4'), 168.9 (OCOCH₃), 165.9 (C_1'), 165.5 (C9), 151.5 (C7), 145.9 (C2), 141.8 (C1), 133.2 (C4), 123.4 (C6), 121.8 (C5), 116.8 (C8), 111.3 (C3), 84.1 (C₁(CH₃)₃), 83.5 (C₄(CH₃)₃), 73.5 (C_2'), 71.0 (C_3'), 56.1 (OMe), 28.1 (C₄(CH₃)₃), 28.0 (C₁(CH₃)₃), 20.8 (OCOCH₃). Calc. C 59.99, H 6.71, O 33.30. Anal. C₂₄H₃₂O₁₀ for C 59.79, H 6.73, O 33.48.

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 molecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. Only one component of the disordered atoms is shown for clarity.
	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. Only one component of the disordered atoms is shown for clarity.

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

Crystal data top

C₂₄H₃₂O₁₀	F(000) = 512
M_r = 480.50	D_x = 1.280 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 5994 reflections
a = 5.9894 (1) Å	θ = 4.2–74.3°
b = 10.6483 (1) Å	µ = 0.84 mm⁻¹
c = 19.6676 (2) Å	T = 100 K
β = 96.324 (1)°	Block, colourless
V = 1246.71 (3) Å³	0.30 × 0.25 × 0.20 mm
Z = 2

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4800 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4762 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.011
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.5°, θ_min = 4.5°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→12
T_min = 0.736, T_max = 1.000	l = −16→24
7492 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.057	w = 1/[σ²(F_o²) + (0.0976P)² + 0.9408P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.159	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.56 e Å⁻³
4800 reflections	Δρ_min = −0.56 e Å⁻³
326 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
113 restraints	Extinction coefficient: 0.0092 (14)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2185 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.0 (2)

Crystal data top

C₂₄H₃₂O₁₀	V = 1246.71 (3) Å³
M_r = 480.50	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 5.9894 (1) Å	µ = 0.84 mm⁻¹
b = 10.6483 (1) Å	T = 100 K
c = 19.6676 (2) Å	0.30 × 0.25 × 0.20 mm
β = 96.324 (1)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4800 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4762 reflections with I > 2σ(I)
T_min = 0.736, T_max = 1.000	R_int = 0.011
7492 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.159	Δρ_max = 0.56 e Å⁻³
S = 1.04	Δρ_min = −0.56 e Å⁻³
4800 reflections	Absolute structure: Flack (1983), 2185 Friedel pairs
326 parameters	Absolute structure parameter: 0.0 (2)
113 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	Occ. (<1)
O7	0.4371 (4)	0.5005 (2)	−0.08067 (10)	0.0278 (5)
O9	0.6166 (4)	0.3370 (2)	−0.16084 (11)	0.0328 (5)
O11	0.4029 (4)	0.1948 (2)	−0.11472 (11)	0.0292 (5)
O22	1.3631 (4)	0.6050 (2)	0.41763 (10)	0.0310 (5)
O26	1.0669 (4)	0.2356 (2)	0.32468 (11)	0.0347 (5)
O29	1.2096 (4)	0.7128 (2)	0.32469 (12)	0.0397 (6)
C8	0.3467 (6)	0.5990 (3)	−0.04224 (16)	0.0336 (7)
H8A	0.2064	0.6296	−0.0671	0.050*
H8B	0.4550	0.6681	−0.0359	0.050*
H8C	0.3167	0.5667	0.0025	0.050*
C10	0.4462 (5)	0.2526 (3)	−0.16343 (14)	0.0242 (6)
C19	0.3237 (7)	0.2434 (4)	−0.23373 (16)	0.0424 (8)
H19A	0.2985	0.1548	−0.2458	0.064*
H19B	0.4135	0.2828	−0.2666	0.064*
H19C	0.1788	0.2865	−0.2349	0.064*
C16	1.1830 (5)	0.4859 (3)	0.33031 (14)	0.0276 (6)
H16	1.3204	0.4323	0.3387	0.033*	0.50
H16'	1.3135	0.4291	0.3258	0.033*	0.50
C17	1.0120 (6)	0.4317 (3)	0.3743 (2)	0.0398 (8)
H17	1.1049	0.4023	0.4167	0.048*	0.50
H17'	1.0675	0.4238	0.4240	0.048*	0.50
C21	1.2513 (5)	0.6166 (3)	0.35547 (15)	0.0281 (6)
C23	1.4332 (6)	0.7160 (3)	0.46048 (15)	0.0288 (6)
C24	1.5891 (5)	0.7998 (3)	0.42441 (15)	0.0307 (6)
H24A	1.5054	0.8372	0.3838	0.046*
H24B	1.7137	0.7496	0.4107	0.046*
H24C	1.6486	0.8666	0.4556	0.046*
C27	1.0144 (9)	0.1107 (4)	0.29275 (19)	0.0545 (11)
C28	1.2436 (10)	0.0608 (4)	0.2822 (3)	0.0677 (13)
H28A	1.3319	0.0486	0.3266	0.102*
H28B	1.3203	0.1210	0.2550	0.102*
H28C	1.2275	−0.0197	0.2579	0.102*
C30	1.5590 (6)	0.6561 (3)	0.52404 (16)	0.0350 (7)
H30A	1.6931	0.6130	0.5115	0.052*
H30B	1.4609	0.5953	0.5435	0.052*
H30C	1.6036	0.7214	0.5579	0.052*
C31	1.2248 (6)	0.7844 (3)	0.47798 (18)	0.0377 (7)
H31A	1.1468	0.8215	0.4364	0.057*
H31B	1.2684	0.8509	0.5112	0.057*
H31C	1.1248	0.7249	0.4976	0.057*
C33	0.8689 (11)	0.1311 (6)	0.2251 (2)	0.0820 (18)
H33A	0.9517	0.1817	0.1946	0.123*
H33B	0.7308	0.1751	0.2335	0.123*
H33C	0.8306	0.0497	0.2037	0.123*
C34	0.9014 (10)	0.0297 (4)	0.3424 (2)	0.0612 (12)
H34A	1.0038	0.0178	0.3843	0.092*
H34B	0.8635	−0.0521	0.3214	0.092*
H34C	0.7640	0.0712	0.3536	0.092*
C25	0.9092 (6)	0.3113 (4)	0.34205 (19)	0.0426 (9)
O15	1.1121 (8)	0.4798 (6)	0.2571 (3)	0.0228 (10)	0.50
O18	0.8662 (8)	0.5278 (4)	0.3987 (3)	0.0307 (7)	0.50
H18	0.7365	0.4983	0.3996	0.046*	0.50
O20	1.4905 (9)	0.4773 (6)	0.2372 (3)	0.0428 (11)	0.50
O32	0.7017 (9)	0.3148 (6)	0.3472 (3)	0.0330 (11)	0.50
C5	0.9150 (8)	0.4130 (9)	0.0399 (2)	0.0257 (15)	0.50
C6	0.7206 (15)	0.4724 (12)	0.0112 (5)	0.0288 (12)	0.50
H6	0.6447	0.5298	0.0376	0.035*	0.50
C1	0.637 (2)	0.4479 (19)	−0.0563 (5)	0.0238 (10)	0.50
C2	0.748 (2)	0.3639 (18)	−0.0950 (4)	0.0208 (17)	0.50
C3	0.9427 (17)	0.3045 (11)	−0.0662 (4)	0.0312 (15)	0.50
H3	1.0185	0.2471	−0.0926	0.037*	0.50
C4	1.0261 (11)	0.3290 (9)	0.0013 (3)	0.0329 (17)	0.50
H4	1.1590	0.2884	0.0209	0.039*	0.50
C12	0.9996 (9)	0.4465 (5)	0.1183 (3)	0.0235 (9)	0.50
H12	0.8911	0.4701	0.1477	0.028*	0.50
C13	1.2118 (9)	0.4426 (6)	0.1434 (3)	0.0247 (8)	0.50
H13	1.3169	0.4233	0.1121	0.030*	0.50
C14	1.3058 (13)	0.4652 (7)	0.2160 (3)	0.0211 (10)	0.50
O15'	1.0409 (8)	0.5056 (6)	0.2672 (3)	0.0228 (10)	0.50
O18'	0.8121 (7)	0.5086 (4)	0.3612 (3)	0.0307 (7)	0.50
H18'	0.6982	0.4653	0.3667	0.046*	0.50
O20'	1.3768 (11)	0.4694 (8)	0.2179 (4)	0.0428 (11)	0.50
O32'	0.7143 (9)	0.2721 (6)	0.3262 (3)	0.0330 (11)	0.50
C5'	0.9726 (8)	0.4098 (9)	0.0235 (2)	0.0257 (15)	0.50
C6'	0.7657 (16)	0.4690 (12)	0.0099 (5)	0.0288 (12)	0.50
H6'	0.7173	0.5273	0.0418	0.035*	0.50
C1'	0.6298 (18)	0.4431 (19)	−0.0504 (6)	0.0238 (10)	0.50
C2'	0.7007 (19)	0.3579 (18)	−0.0971 (5)	0.0208 (17)	0.50
C3'	0.9076 (17)	0.2987 (11)	−0.0835 (4)	0.0312 (15)	0.50
H3'	0.9561	0.2405	−0.1154	0.037*	0.50
C4'	1.0436 (11)	0.3246 (9)	−0.0232 (3)	0.0329 (17)	0.50
H4'	1.1850	0.2841	−0.0139	0.039*	0.50
C12'	1.0951 (9)	0.4272 (5)	0.0934 (3)	0.0235 (9)	0.50
H12'	1.2474	0.4006	0.0988	0.028*	0.50
C13'	1.0193 (11)	0.4750 (6)	0.1491 (3)	0.0247 (8)	0.50
H13'	0.8696	0.5049	0.1482	0.030*	0.50
C14'	1.1755 (11)	0.4797 (6)	0.2121 (3)	0.0211 (10)	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O7	0.0346 (10)	0.0278 (10)	0.0191 (9)	0.0055 (9)	−0.0054 (7)	−0.0043 (8)
O9	0.0478 (12)	0.0274 (11)	0.0254 (10)	−0.0106 (10)	0.0145 (9)	−0.0049 (8)
O11	0.0318 (10)	0.0317 (11)	0.0233 (10)	−0.0058 (9)	−0.0012 (8)	0.0043 (9)
O22	0.0488 (12)	0.0215 (10)	0.0205 (10)	−0.0008 (9)	−0.0068 (8)	0.0014 (8)
O26	0.0441 (13)	0.0264 (11)	0.0310 (11)	−0.0172 (9)	−0.0076 (9)	0.0017 (9)
O29	0.0428 (13)	0.0344 (13)	0.0372 (12)	−0.0119 (10)	−0.0169 (10)	0.0191 (10)
C8	0.0429 (17)	0.0298 (16)	0.0265 (14)	0.0091 (14)	−0.0031 (12)	−0.0054 (12)
C10	0.0298 (14)	0.0209 (13)	0.0223 (13)	0.0043 (11)	0.0047 (10)	−0.0010 (11)
C19	0.069 (2)	0.0356 (18)	0.0203 (14)	0.0014 (17)	−0.0026 (14)	0.0006 (13)
C16	0.0322 (14)	0.0292 (15)	0.0193 (13)	−0.0102 (12)	−0.0072 (11)	0.0050 (11)
C17	0.0406 (18)	0.0251 (16)	0.056 (2)	0.0031 (14)	0.0179 (15)	0.0153 (15)
C21	0.0253 (13)	0.0311 (15)	0.0262 (14)	−0.0063 (12)	−0.0051 (10)	0.0077 (13)
C23	0.0421 (16)	0.0189 (13)	0.0248 (14)	−0.0024 (12)	0.0000 (11)	0.0002 (11)
C24	0.0353 (15)	0.0263 (15)	0.0299 (15)	0.0005 (12)	0.0019 (11)	0.0065 (12)
C27	0.092 (3)	0.0381 (18)	0.0305 (17)	−0.038 (2)	−0.0078 (18)	−0.0010 (15)
C28	0.111 (4)	0.040 (2)	0.056 (2)	−0.019 (2)	0.025 (2)	−0.0203 (19)
C30	0.056 (2)	0.0237 (14)	0.0226 (15)	−0.0055 (14)	−0.0075 (13)	0.0000 (12)
C31	0.0429 (17)	0.0308 (17)	0.0406 (18)	−0.0026 (14)	0.0105 (14)	−0.0017 (14)
C33	0.121 (4)	0.083 (3)	0.036 (2)	−0.070 (3)	−0.017 (2)	0.015 (2)
C34	0.099 (3)	0.047 (2)	0.0349 (18)	−0.040 (2)	−0.0053 (18)	0.0038 (16)
C25	0.0330 (16)	0.045 (2)	0.0472 (19)	−0.0140 (15)	−0.0096 (13)	0.0300 (17)
O15	0.019 (3)	0.027 (3)	0.0207 (17)	−0.0050 (19)	−0.0049 (17)	0.0026 (15)
O18	0.0330 (17)	0.0225 (15)	0.036 (2)	−0.0023 (13)	0.0025 (16)	−0.0022 (16)
O20	0.025 (2)	0.063 (2)	0.039 (2)	−0.010 (3)	−0.0039 (18)	0.009 (2)
O32	0.0285 (13)	0.029 (3)	0.040 (3)	−0.0141 (19)	−0.0021 (17)	0.0005 (19)
C5	0.013 (3)	0.0270 (18)	0.037 (3)	−0.012 (3)	0.001 (2)	0.011 (3)
C6	0.033 (3)	0.0180 (15)	0.0315 (16)	−0.002 (2)	−0.0128 (19)	0.0007 (12)
C1	0.0289 (15)	0.0196 (16)	0.0222 (19)	−0.0039 (13)	0.0000 (14)	0.0016 (17)
C2	0.008 (5)	0.0230 (19)	0.0321 (16)	−0.011 (4)	0.0036 (16)	−0.0013 (12)
C3	0.017 (3)	0.0249 (18)	0.049 (4)	−0.006 (2)	−0.008 (3)	−0.004 (3)
C4	0.0279 (18)	0.0281 (19)	0.042 (5)	−0.0003 (16)	0.001 (3)	0.008 (4)
C12	0.014 (2)	0.0207 (19)	0.036 (3)	0.0019 (16)	0.0043 (15)	0.0121 (18)
C13	0.0324 (18)	0.028 (2)	0.0122 (16)	−0.0036 (16)	−0.0053 (15)	−0.0027 (15)
C14	0.029 (3)	0.0229 (19)	0.0102 (16)	−0.012 (3)	−0.002 (3)	0.0026 (14)
O15'	0.019 (3)	0.027 (3)	0.0207 (17)	−0.0050 (19)	−0.0049 (17)	0.0026 (15)
O18'	0.0330 (17)	0.0225 (15)	0.036 (2)	−0.0023 (13)	0.0025 (16)	−0.0022 (16)
O20'	0.025 (2)	0.063 (2)	0.039 (2)	−0.010 (3)	−0.0039 (18)	0.009 (2)
O32'	0.0285 (13)	0.029 (3)	0.040 (3)	−0.0141 (19)	−0.0021 (17)	0.0005 (19)
C5'	0.013 (3)	0.0270 (18)	0.037 (3)	−0.012 (3)	0.001 (2)	0.011 (3)
C6'	0.033 (3)	0.0180 (15)	0.0315 (16)	−0.002 (2)	−0.0128 (19)	0.0007 (12)
C1'	0.0289 (15)	0.0196 (16)	0.0222 (19)	−0.0039 (13)	0.0000 (14)	0.0016 (17)
C2'	0.008 (5)	0.0230 (19)	0.0321 (16)	−0.011 (4)	0.0036 (16)	−0.0013 (12)
C3'	0.017 (3)	0.0249 (18)	0.049 (4)	−0.006 (2)	−0.008 (3)	−0.004 (3)
C4'	0.0279 (18)	0.0281 (19)	0.042 (5)	−0.0003 (16)	0.001 (3)	0.008 (4)
C12'	0.014 (2)	0.0207 (19)	0.036 (3)	0.0019 (16)	0.0043 (15)	0.0121 (18)
C13'	0.0324 (18)	0.028 (2)	0.0122 (16)	−0.0036 (16)	−0.0053 (15)	−0.0027 (15)
C14'	0.029 (3)	0.0229 (19)	0.0102 (16)	−0.012 (3)	−0.002 (3)	0.0026 (14)

Geometric parameters (Å, º) top

O7—C1	1.361 (5)	C31—H31A	0.9800
O7—C1'	1.381 (6)	C31—H31B	0.9800
O7—C8	1.434 (4)	C31—H31C	0.9800
O9—C2'	1.318 (6)	C33—H33A	0.9800
O9—C10	1.357 (4)	C33—H33B	0.9800
O9—C2	1.468 (5)	C33—H33C	0.9800
O11—C10	1.191 (4)	C34—H34A	0.9800
O22—C21	1.333 (3)	C34—H34B	0.9800
O22—C23	1.485 (4)	C34—H34C	0.9800
O26—C25	1.316 (5)	C25—O32'	1.247 (6)
O26—C27	1.489 (4)	C25—O32	1.258 (6)
O29—C21	1.202 (4)	O15—C14	1.494 (8)
C8—H8A	0.9800	O18—H18	0.8400
C8—H8B	0.9800	O20—C14	1.146 (9)
C8—H8C	0.9800	C5—C6	1.3900
C10—C19	1.495 (4)	C5—C4	1.3900
C19—H19A	0.9800	C5—C12	1.608 (7)
C19—H19B	0.9800	C6—C1	1.3900
C19—H19C	0.9800	C6—H6	0.9500
C16—O15'	1.441 (5)	C1—C2	1.3900
C16—O15	1.457 (5)	C2—C3	1.3900
C16—C21	1.519 (4)	C3—C4	1.3900
C16—C17	1.525 (4)	C3—H3	0.9500
C16—H16	1.0000	C4—H4	0.9500
C16—H16'	1.0000	C12—C13	1.313 (7)
C17—O18'	1.450 (5)	C12—H12	0.9500
C17—O18	1.460 (5)	C13—C14	1.495 (7)
C17—C25	1.530 (6)	C13—H13	0.9500
C17—H17	1.0000	O15'—C14'	1.447 (7)
C17—H17'	1.0000	O18'—H18'	0.8400
C23—C31	1.517 (5)	O20'—C14'	1.203 (9)
C23—C24	1.523 (4)	C5'—C6'	1.3900
C23—C30	1.526 (4)	C5'—C4'	1.3900
C24—H24A	0.9800	C5'—C12'	1.497 (6)
C24—H24B	0.9800	C6'—C1'	1.3900
C24—H24C	0.9800	C6'—H6'	0.9500
C27—C28	1.508 (8)	C1'—C2'	1.3900
C27—C34	1.517 (5)	C2'—C3'	1.3900
C27—C33	1.524 (6)	C3'—C4'	1.3900
C28—H28A	0.9800	C3'—H3'	0.9500
C28—H28B	0.9800	C4'—H4'	0.9500
C28—H28C	0.9800	C12'—C13'	1.333 (7)
C30—H30A	0.9800	C12'—H12'	0.9500
C30—H30B	0.9800	C13'—C14'	1.468 (7)
C30—H30C	0.9800	C13'—H13'	0.9500

C1—O7—C8	119.0 (6)	C23—C31—H31B	109.5
C1'—O7—C8	116.3 (5)	H31A—C31—H31B	109.5
C2'—O9—C10	110.8 (9)	C23—C31—H31C	109.5
C10—O9—C2	119.4 (8)	H31A—C31—H31C	109.5
C21—O22—C23	121.9 (2)	H31B—C31—H31C	109.5
C25—O26—C27	122.2 (3)	C27—C33—H33A	109.5
O7—C8—H8A	109.5	C27—C33—H33B	109.5
O7—C8—H8B	109.5	H33A—C33—H33B	109.5
H8A—C8—H8B	109.5	C27—C33—H33C	109.5
O7—C8—H8C	109.5	H33A—C33—H33C	109.5
H8A—C8—H8C	109.5	H33B—C33—H33C	109.5
H8B—C8—H8C	109.5	C27—C34—H34A	109.5
O11—C10—O9	122.8 (3)	C27—C34—H34B	109.5
O11—C10—C19	125.6 (3)	H34A—C34—H34B	109.5
O9—C10—C19	111.6 (3)	C27—C34—H34C	109.5
C10—C19—H19A	109.5	H34A—C34—H34C	109.5
C10—C19—H19B	109.5	H34B—C34—H34C	109.5
H19A—C19—H19B	109.5	O32'—C25—O26	114.1 (4)
C10—C19—H19C	109.5	O32—C25—O26	141.5 (4)
H19A—C19—H19C	109.5	O32'—C25—C17	135.1 (5)
H19B—C19—H19C	109.5	O32—C25—C17	107.3 (4)
O15'—C16—C21	105.1 (3)	O26—C25—C17	110.7 (3)
O15—C16—C21	113.7 (4)	C16—O15—C14	112.4 (4)
O15'—C16—C17	100.0 (3)	C17—O18—H18	109.5
O15—C16—C17	113.8 (3)	C6—C5—C4	120.0
C21—C16—C17	109.6 (3)	C6—C5—C12	116.8 (6)
O15'—C16—H16	128.5	C4—C5—C12	123.2 (6)
O15—C16—H16	106.4	C5—C6—C1	120.0
C21—C16—H16	106.4	C5—C6—H6	120.0
C17—C16—H16	106.4	C1—C6—H6	120.0
O15'—C16—H16'	113.8	O7—C1—C2	121.8 (8)
O15—C16—H16'	91.7	O7—C1—C6	117.9 (7)
C21—C16—H16'	113.5	C2—C1—C6	120.0
C17—C16—H16'	113.7	C1—C2—C3	120.0
O18'—C17—C16	106.2 (3)	C1—C2—O9	111.4 (7)
O18—C17—C16	112.6 (3)	C3—C2—O9	127.9 (8)
O18'—C17—C25	96.5 (3)	C4—C3—C2	120.0
O18—C17—C25	119.7 (3)	C4—C3—H3	120.0
C16—C17—C25	110.3 (3)	C2—C3—H3	120.0
O18'—C17—H17	134.3	C3—C4—C5	120.0
O18—C17—H17	104.2	C3—C4—H4	120.0
C16—C17—H17	104.2	C5—C4—H4	120.0
C25—C17—H17	104.2	C13—C12—C5	122.9 (6)
O18'—C17—H17'	113.6	C13—C12—H12	118.6
O18—C17—H17'	83.4	C5—C12—H12	118.6
C16—C17—H17'	114.5	C12—C13—C14	127.0 (6)
C25—C17—H17'	114.2	C12—C13—H13	116.5
O29—C21—O22	126.6 (3)	C14—C13—H13	116.5
O29—C21—C16	125.7 (3)	O20—C14—O15	124.5 (6)
O22—C21—C16	107.7 (2)	O20—C14—C13	127.8 (6)
O22—C23—C31	108.8 (3)	O15—C14—C13	107.5 (6)
O22—C23—C24	110.6 (2)	C16—O15'—C14'	107.0 (4)
C31—C23—C24	112.7 (3)	C17—O18'—H18'	109.5
O22—C23—C30	102.5 (2)	C6'—C5'—C4'	120.0
C31—C23—C30	111.0 (3)	C6'—C5'—C12'	117.2 (5)
C24—C23—C30	110.7 (3)	C4'—C5'—C12'	122.2 (6)
C23—C24—H24A	109.5	C1'—C6'—C5'	120.0
C23—C24—H24B	109.5	C1'—C6'—H6'	120.0
H24A—C24—H24B	109.5	C5'—C6'—H6'	120.0
C23—C24—H24C	109.5	O7—C1'—C6'	131.5 (8)
H24A—C24—H24C	109.5	O7—C1'—C2'	107.8 (8)
H24B—C24—H24C	109.5	C6'—C1'—C2'	120.0
O26—C27—C28	102.7 (3)	O9—C2'—C3'	110.2 (8)
O26—C27—C34	108.9 (3)	O9—C2'—C1'	128.8 (8)
C28—C27—C34	111.5 (4)	C3'—C2'—C1'	120.0
O26—C27—C33	108.3 (4)	C2'—C3'—C4'	120.0
C28—C27—C33	111.8 (4)	C2'—C3'—H3'	120.0
C34—C27—C33	113.0 (4)	C4'—C3'—H3'	120.0
C27—C28—H28A	109.5	C3'—C4'—C5'	120.0
C27—C28—H28B	109.5	C3'—C4'—H4'	120.0
H28A—C28—H28B	109.5	C5'—C4'—H4'	120.0
C27—C28—H28C	109.5	C13'—C12'—C5'	128.8 (5)
H28A—C28—H28C	109.5	C13'—C12'—H12'	115.6
H28B—C28—H28C	109.5	C5'—C12'—H12'	115.6
C23—C30—H30A	109.5	C12'—C13'—C14'	117.6 (6)
C23—C30—H30B	109.5	C12'—C13'—H13'	121.2
H30A—C30—H30B	109.5	C14'—C13'—H13'	121.2
C23—C30—H30C	109.5	O20'—C14'—O15'	125.5 (6)
H30A—C30—H30C	109.5	O20'—C14'—C13'	128.0 (6)
H30B—C30—H30C	109.5	O15'—C14'—C13'	106.4 (5)
C23—C31—H31A	109.5

C2'—O9—C10—O11	−9.0 (7)	C6—C1—C2—C3	0.0
C2—O9—C10—O11	−2.9 (7)	O7—C1—C2—O9	−3.1 (9)
C2'—O9—C10—C19	170.5 (6)	C6—C1—C2—O9	171.6 (14)
C2—O9—C10—C19	176.6 (6)	C2'—O9—C2—C1	−46 (8)
O15'—C16—C17—O18'	−43.9 (4)	C10—O9—C2—C1	−80.4 (7)
O15—C16—C17—O18'	−62.3 (5)	C2'—O9—C2—C3	124 (9)
C21—C16—C17—O18'	66.2 (4)	C10—O9—C2—C3	90.4 (12)
O15'—C16—C17—O18	−77.0 (4)	C1—C2—C3—C4	0.0
O15—C16—C17—O18	−95.5 (5)	O9—C2—C3—C4	−170.1 (16)
C21—C16—C17—O18	33.1 (4)	C2—C3—C4—C5	0.0
O15'—C16—C17—C25	59.5 (4)	C6—C5—C4—C3	0.0
O15—C16—C17—C25	41.1 (4)	C12—C5—C4—C3	179.9 (8)
C21—C16—C17—C25	169.6 (2)	C6—C5—C12—C13	−151.1 (8)
C23—O22—C21—O29	6.2 (5)	C4—C5—C12—C13	29.1 (9)
C23—O22—C21—C16	−173.2 (3)	C5—C12—C13—C14	−176.5 (7)
O15'—C16—C21—O29	−6.2 (5)	C16—O15—C14—O20	−11.7 (10)
O15—C16—C21—O29	15.7 (5)	C16—O15—C14—C13	172.4 (5)
C17—C16—C21—O29	−112.9 (4)	C12—C13—C14—O20	−169.6 (8)
O15'—C16—C21—O22	173.3 (3)	C12—C13—C14—O15	6.0 (9)
O15—C16—C21—O22	−164.8 (3)	O15—C16—O15'—C14'	−14.2 (10)
C17—C16—C21—O22	66.6 (3)	C21—C16—O15'—C14'	101.9 (5)
C21—O22—C23—C31	64.2 (3)	C17—C16—O15'—C14'	−144.5 (5)
C21—O22—C23—C24	−60.1 (4)	C4'—C5'—C6'—C1'	0.0
C21—O22—C23—C30	−178.2 (3)	C12'—C5'—C6'—C1'	−171.2 (8)
C25—O26—C27—C28	179.7 (3)	C1—O7—C1'—C6'	114 (16)
C25—O26—C27—C34	−62.0 (5)	C8—O7—C1'—C6'	−5.3 (18)
C25—O26—C27—C33	61.3 (5)	C1—O7—C1'—C2'	−56 (14)
C27—O26—C25—O32'	−3.6 (5)	C8—O7—C1'—C2'	−175.5 (4)
C27—O26—C25—O32	8.4 (8)	C5'—C6'—C1'—O7	−169.2 (19)
C27—O26—C25—C17	179.3 (3)	C5'—C6'—C1'—C2'	0.0
O18'—C17—C25—O32'	−18.1 (7)	C10—O9—C2'—C3'	105.5 (8)
O18—C17—C25—O32'	5.0 (7)	C2—O9—C2'—C3'	−43 (8)
C16—C17—C25—O32'	−128.0 (6)	C10—O9—C2'—C1'	−86.2 (10)
O18'—C17—C25—O32	−27.7 (5)	C2—O9—C2'—C1'	125 (9)
O18—C17—C25—O32	−4.6 (6)	O7—C1'—C2'—O9	4.3 (9)
C16—C17—C25—O32	−137.6 (4)	C6'—C1'—C2'—O9	−167.3 (17)
O18'—C17—C25—O26	158.2 (3)	O7—C1'—C2'—C3'	171.5 (16)
O18—C17—C25—O26	−178.7 (3)	C6'—C1'—C2'—C3'	0.0
C16—C17—C25—O26	48.3 (4)	O9—C2'—C3'—C4'	169.5 (14)
O15'—C16—O15—C14	155.9 (17)	C1'—C2'—C3'—C4'	0.0
C21—C16—O15—C14	84.7 (6)	C2'—C3'—C4'—C5'	0.0
C17—C16—O15—C14	−148.9 (5)	C6'—C5'—C4'—C3'	0.0
C4—C5—C6—C1	0.0	C12'—C5'—C4'—C3'	170.8 (8)
C12—C5—C6—C1	−179.9 (7)	C6'—C5'—C12'—C13'	12.2 (11)
C1'—O7—C1—C2	125 (15)	C4'—C5'—C12'—C13'	−158.8 (7)
C8—O7—C1—C2	−171.5 (5)	C5'—C12'—C13'—C14'	179.1 (6)
C1'—O7—C1—C6	−49 (14)	C16—O15'—C14'—O20'	−13.8 (10)
C8—O7—C1—C6	13.7 (15)	C16—O15'—C14'—C13'	168.8 (5)
C5—C6—C1—O7	174.9 (17)	C12'—C13'—C14'—O20'	16.2 (11)
C5—C6—C1—C2	0.0	C12'—C13'—C14'—O15'	−166.5 (6)
O7—C1—C2—C3	−174.7 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O18—H18···O32	0.84	2.21	2.631 (8)	111
O18—H18···O22ⁱ	0.84	2.57	3.185 (5)	131

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₃₂O₁₀
M_r	480.50
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	5.9894 (1), 10.6483 (1), 19.6676 (2)
β (°)	96.324 (1)
V (Å³)	1246.71 (3)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.84
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.736, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7492, 4800, 4762
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.159, 1.04
No. of reflections	4800
No. of parameters	326
No. of restraints	113
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.56
Absolute structure	Flack (1983), 2185 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
O18—H18···O32	0.84	2.21	2.631 (8)	111
O18—H18···O22ⁱ	0.84	2.57	3.185 (5)	131

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 (grant No. UM·C/HIR/MOHE/SC/12).

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, 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
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o568-o569

doi:10.1107/S1600536812002784

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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