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

In the title mol-ecule, C(24)H(32)O(10), 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 hy-droxy tert-butyl ester side chain are disordered over two sets of sites in a 50:50 ratio. 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 also partakes in an intra-molecular O-H⋯O inter-action.

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 = 480.50

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.159

S = 1.04

4800 reflections

326 parameters

113 restraints

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.56 e Å−3

Absolute structure: Flack (1983 ▶), 2185 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/S1600536812002784/hb6612sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812002784/hb6612Isup3.cml

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

C24H32O10	F(000) = 512
Mr = 480.50	Dx = 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

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	Rint = 0.011
Detector resolution: 10.4041 pixels mm-1	θmax = 74.5°, θmin = 4.5°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→12
Tmin = 0.736, Tmax = 1.000	l = −16→24
7492 measured reflections

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(Fo2) + (0.0976P)2 + 0.9408P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.159	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.56 e Å−3
4800 reflections	Δρmin = −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	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	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

	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)

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)

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

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) .