1,4-Di-tert-butyl (2R,3R)-2-({(2E)-3-[4-(acet-yloxy)phen-yl]prop-2-eno-yl}-oxy)-3-hy-droxy-butane-dioate.

The title compound, C(23)H(30)O(9), 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 supra-molecular chains along the a axis mediated by hy-droxy-carbonyl O-H⋯O hydrogen bonds feature in the crystal packing. The same H atom is also involved in an intra-molecular O-H⋯O inter-action.

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 = 450.47

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.131

S = 1.05

4603 reflections

300 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 1849 Friedel pairs

Flack parameter: 0.0 (2)

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681200236X/hb6610sup1.cif

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

Supplementary material file. DOI: 10.1107/S160053681200236X/hb6610Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H30O9	F(000) = 960
Mr = 450.47	Dx = 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

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	Rint = 0.044
Detector resolution: 10.4041 pixels mm-1	θmax = 74.6°, θmin = 3.8°
ω scan	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −10→7
Tmin = 0.230, Tmax = 1.000	l = −56→58
9078 measured reflections

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(Fo2) + (0.0669P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4603 reflections	Δρmax = 0.28 e Å−3
300 parameters	Δρmin = −0.30 e Å−3
0 restraints	Absolute structure: Flack (1983), 1849 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.0 (2)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .