4-(Dimeth­oxy­meth­yl)phenyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyran­oside

Zipp, C.F.; Fernandes, M.; Marques, H.M.; Michael, J.P.

doi:10.1107/S160053681201121X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1202

doi:10.1107/S160053681201121X

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4-(Dimethoxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Caitlin F. Zipp,^a Manuel Fernandes,^a Helder M. Marques ^a ^* and Joseph P. Michael ^a

^aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South Africa
^*Correspondence e-mail: Helder.Marques@wits.ac.za

(Received 22 February 2012; accepted 14 March 2012; online 28 March 2012)

The enantiomerically pure title compound, C₂₃H₃₀O₁₂, crystallizes in the chiral space group P2₁2₁2₁. The O-acetylated-glucopyranoside moiety adopts a chair conformation. Numerous C—H⋯O interactions as well as a C—H⋯π interaction are present in the crystal structure.

Related literature

For similar compounds, see: Bin et al. (2008 ); Ansari et al. (2006 ). For the use of sugars as water-solubilizing agents in macrocycle chemistry, see: Sol et al. (1997 ); Maillard et al. (1993 ); Oulmi et al. (1995 ). For the role of sugars in biological systems, especially proteins, see: Floyd et al. (2009 ).

Experimental

Crystal data

C₂₃H₃₀O₁₂
M_r = 498.47
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.9004 (2) Å
b = 10.9961 (3) Å
c = 29.2289 (8) Å
V = 2539.22 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 173 K
0.45 × 0.32 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
13406 measured reflections
3493 independent reflections
2644 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.102
S = 0.97
3493 reflections
322 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O11ⁱ	1.00	2.44	3.347 (3)	151
C12—H12⋯O4ⁱⁱ	0.95	2.45	3.321 (3)	152
C19—H19A⋯O3ⁱⁱⁱ	0.98	2.54	3.510 (3)	171
C19—H19C⋯O8^iv	0.98	2.49	3.414 (3)	157
C21—H21C⋯O10^iv	0.98	2.29	3.252 (4)	168
C23—H23C⋯Cg^v	0.98	2.71	3.615 (4)	153
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (v) x, y+1, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and SCHAKAL99 (Keller, 1999 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681201121X/mw2057sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201121X/mw2057Isup2.hkl

checkCIF report

Comment top

Glycosylation is common in nature, with a large proportion of all proteins bearing sugar residues (Floyd et al., 2009). The title compound was synthesized as a precursor to a biomimetic model for vitamin B12_a (aquacobalamin) as sugars can play a useful role in the solubilizing of large organic systems, such as glycosylated porphyrins (Sol et al., 1997; Maillard et al., 1993; Oulmi et al., 1995).

Related literature top

For similar compounds, see: Bin et al. (2008); Ansari et al. (2006). For the use of sugars as water-solubilizing agents in macrocycle chemistry, see: Sol et al. (1997); Maillard et al. (1993); Oulmi et al. (1995). For the role of sugars in biological systems, especially proteins, see: Floyd et al. (2009).

Experimental top

The title compound was synthesized from p-hydroxybenzaldehyde and 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide in the presence of NaOH. The product was purified by column chromatography and recrystallized from acidified methanol to yield colourless plate-like crystals.

Structure description top

For similar compounds, see: Bin et al. (2008); Ansari et al. (2006). For the use of sugars as water-solubilizing agents in macrocycle chemistry, see: Sol et al. (1997); Maillard et al. (1993); Oulmi et al. (1995). For the role of sugars in biological systems, especially proteins, see: Floyd et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL99 (Keller, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Weak hydrogen bonding in the strucuture of (I). Four of the five C—H···O interactions listed in Table 1 are shown, while the location of the C—H···π interactions is indicated with a #.

4-(Dimethoxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside top

Crystal data top

C₂₃H₃₀O₁₂	F(000) = 1056
M_r = 498.47	D_x = 1.304 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3488 reflections
a = 7.9004 (2) Å	θ = 2.3–24.0°
b = 10.9961 (3) Å	µ = 0.11 mm⁻¹
c = 29.2289 (8) Å	T = 173 K
V = 2539.22 (12) Å³	Plate, colourless
Z = 4	0.45 × 0.32 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	2644 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.053
Graphite monochromator	θ_max = 28.0°, θ_min = 2.0°
φ and ω scans	h = −10→10
13406 measured reflections	k = −10→14
3493 independent reflections	l = −38→37

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0567P)²] where P = (F_o² + 2F_c²)/3
3493 reflections	(Δ/σ)_max = 0.001
322 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₃H₃₀O₁₂	V = 2539.22 (12) Å³
M_r = 498.47	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.9004 (2) Å	µ = 0.11 mm⁻¹
b = 10.9961 (3) Å	T = 173 K
c = 29.2289 (8) Å	0.45 × 0.32 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	2644 reflections with I > 2σ(I)
13406 measured reflections	R_int = 0.053
3493 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 0.97	Δρ_max = 0.25 e Å⁻³
3493 reflections	Δρ_min = −0.20 e Å⁻³
322 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
C1	0.0801 (3)	0.3057 (2)	0.12632 (8)	0.0238 (5)
H1	0.0113	0.2457	0.1086	0.029*
C2	0.2410 (3)	0.3384 (2)	0.10042 (8)	0.0219 (5)
H2	0.3164	0.3905	0.1197	0.026*
C3	0.1944 (3)	0.4037 (2)	0.05649 (8)	0.0225 (5)
H3	0.1373	0.3461	0.0350	0.027*
C4	0.0790 (3)	0.5105 (2)	0.06664 (8)	0.0236 (5)
H4	0.1420	0.5753	0.0836	0.028*
C5	−0.0749 (3)	0.4686 (2)	0.09422 (8)	0.0254 (5)
H5	−0.1399	0.4077	0.0759	0.031*
C6	−0.1907 (3)	0.5704 (2)	0.10783 (9)	0.0313 (6)
H6A	−0.2358	0.6113	0.0802	0.038*
H6B	−0.2873	0.5381	0.1257	0.038*
C7	0.0063 (3)	0.1934 (2)	0.19310 (8)	0.0266 (5)
C8	0.0622 (4)	0.1381 (2)	0.23282 (9)	0.0355 (7)
H8	0.1776	0.1437	0.2417	0.043*
C9	−0.0526 (4)	0.0745 (3)	0.25957 (9)	0.0389 (7)
H9	−0.0149	0.0360	0.2868	0.047*
C10	−0.2229 (4)	0.0663 (2)	0.24709 (9)	0.0349 (6)
C11	−0.2725 (4)	0.1186 (2)	0.20664 (10)	0.0353 (6)
H11	−0.3865	0.1100	0.1968	0.042*
C12	−0.1597 (4)	0.1839 (2)	0.17970 (9)	0.0339 (6)
H12	−0.1971	0.2217	0.1523	0.041*
C13	−0.3436 (4)	−0.0023 (3)	0.27751 (10)	0.0439 (7)
H13	−0.3008	−0.0875	0.2804	0.053*
C14	−0.4138 (6)	0.1676 (3)	0.32407 (12)	0.0660 (11)
H14A	−0.3371	0.2205	0.3068	0.099*
H14B	−0.4181	0.1944	0.3560	0.099*
H14C	−0.5274	0.1718	0.3107	0.099*
C15	−0.6115 (6)	−0.0935 (3)	0.27581 (13)	0.0679 (11)
H15A	−0.5587	−0.1741	0.2746	0.102*
H15B	−0.7182	−0.0950	0.2587	0.102*
H15C	−0.6340	−0.0716	0.3077	0.102*
C16	0.4919 (4)	0.2178 (2)	0.09375 (8)	0.0284 (6)
C17	0.5515 (4)	0.0911 (2)	0.08455 (10)	0.0428 (7)
H17A	0.6752	0.0882	0.0865	0.064*
H17B	0.5154	0.0662	0.0539	0.064*
H17C	0.5027	0.0357	0.1073	0.064*
C18	0.4204 (3)	0.3879 (2)	0.00160 (8)	0.0268 (5)
C19	0.5757 (4)	0.4516 (2)	−0.01518 (10)	0.0395 (7)
H19A	0.6324	0.4009	−0.0381	0.059*
H19B	0.6527	0.4660	0.0106	0.059*
H19C	0.5438	0.5296	−0.0289	0.059*
C20	0.0206 (4)	0.6785 (2)	0.01657 (9)	0.0329 (6)
C21	−0.0371 (5)	0.7100 (3)	−0.03023 (10)	0.0481 (8)
H21A	−0.0692	0.7960	−0.0313	0.072*
H21B	−0.1350	0.6597	−0.0383	0.072*
H21C	0.0548	0.6951	−0.0520	0.072*
C22	−0.1382 (4)	0.7733 (3)	0.13249 (11)	0.0464 (8)
C23	−0.0184 (5)	0.8508 (3)	0.15844 (13)	0.0651 (11)
H23A	0.0782	0.8716	0.1389	0.098*
H23B	0.0216	0.8066	0.1855	0.098*
H23C	−0.0759	0.9255	0.1681	0.098*
O1	−0.0151 (2)	0.41192 (14)	0.13529 (5)	0.0264 (4)
O2	0.1293 (2)	0.25639 (15)	0.16843 (5)	0.0283 (4)
O3	0.3219 (2)	0.22387 (14)	0.09025 (5)	0.0257 (4)
O4	0.5794 (3)	0.30351 (17)	0.10281 (7)	0.0401 (5)
O5	0.3456 (2)	0.45309 (14)	0.03546 (5)	0.0249 (4)
O6	0.3683 (3)	0.29251 (16)	−0.01228 (6)	0.0401 (5)
O7	0.0199 (2)	0.55613 (14)	0.02296 (5)	0.0280 (4)
O8	0.0625 (3)	0.74887 (16)	0.04572 (7)	0.0538 (6)
O9	−0.0958 (3)	0.65541 (15)	0.13508 (6)	0.0370 (5)
O10	−0.2594 (4)	0.8089 (2)	0.11206 (10)	0.0741 (8)
O11	−0.3548 (3)	0.0473 (2)	0.32214 (7)	0.0566 (6)
O12	−0.5013 (3)	−0.00697 (19)	0.25616 (7)	0.0510 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0264 (13)	0.0235 (11)	0.0216 (12)	−0.0017 (11)	−0.0011 (11)	−0.0001 (9)
C2	0.0204 (12)	0.0216 (11)	0.0235 (12)	0.0004 (10)	0.0008 (10)	−0.0046 (9)
C3	0.0225 (12)	0.0197 (11)	0.0253 (12)	−0.0027 (10)	0.0022 (11)	−0.0003 (9)
C4	0.0265 (13)	0.0213 (11)	0.0230 (12)	0.0000 (11)	0.0013 (11)	−0.0005 (9)
C5	0.0247 (13)	0.0257 (11)	0.0259 (12)	0.0010 (10)	−0.0008 (11)	0.0006 (9)
C6	0.0295 (15)	0.0337 (13)	0.0309 (14)	0.0078 (12)	0.0020 (12)	−0.0011 (11)
C7	0.0297 (14)	0.0253 (11)	0.0248 (12)	0.0009 (11)	0.0044 (11)	0.0003 (10)
C8	0.0360 (16)	0.0430 (15)	0.0276 (14)	−0.0015 (13)	−0.0046 (13)	0.0055 (11)
C9	0.046 (2)	0.0437 (16)	0.0270 (14)	0.0015 (14)	−0.0033 (13)	0.0115 (12)
C10	0.0400 (17)	0.0347 (14)	0.0299 (14)	0.0026 (13)	0.0057 (13)	0.0056 (11)
C11	0.0287 (14)	0.0391 (14)	0.0382 (16)	0.0037 (12)	0.0046 (13)	0.0074 (12)
C12	0.0332 (16)	0.0394 (14)	0.0290 (14)	0.0050 (13)	0.0043 (12)	0.0097 (11)
C13	0.0493 (19)	0.0431 (16)	0.0393 (17)	0.0007 (15)	0.0052 (15)	0.0149 (13)
C14	0.074 (3)	0.065 (2)	0.059 (2)	−0.012 (2)	0.029 (2)	−0.0096 (17)
C15	0.076 (3)	0.062 (2)	0.066 (2)	−0.023 (2)	0.017 (2)	0.0088 (18)
C16	0.0278 (14)	0.0338 (13)	0.0237 (13)	0.0067 (12)	−0.0010 (11)	0.0011 (10)
C17	0.0434 (18)	0.0376 (14)	0.0474 (17)	0.0151 (14)	0.0015 (15)	−0.0033 (13)
C18	0.0295 (13)	0.0244 (11)	0.0265 (13)	0.0036 (11)	0.0040 (12)	0.0005 (9)
C19	0.0407 (16)	0.0323 (13)	0.0455 (16)	0.0004 (13)	0.0207 (15)	−0.0010 (12)
C20	0.0327 (15)	0.0252 (12)	0.0409 (15)	0.0023 (11)	0.0092 (13)	0.0066 (11)
C21	0.067 (2)	0.0324 (14)	0.0452 (17)	0.0067 (15)	0.0005 (17)	0.0119 (13)
C22	0.052 (2)	0.0367 (15)	0.0510 (18)	0.0163 (15)	0.0011 (17)	−0.0032 (14)
C23	0.077 (3)	0.0392 (16)	0.079 (3)	0.0126 (19)	−0.018 (2)	−0.0202 (17)
O1	0.0287 (10)	0.0289 (8)	0.0217 (8)	0.0038 (7)	0.0024 (8)	0.0015 (7)
O2	0.0272 (10)	0.0340 (9)	0.0236 (9)	−0.0010 (8)	0.0008 (8)	0.0046 (7)
O3	0.0257 (10)	0.0223 (8)	0.0291 (9)	0.0039 (7)	−0.0011 (8)	−0.0021 (7)
O4	0.0261 (10)	0.0378 (10)	0.0564 (13)	0.0012 (9)	−0.0027 (10)	−0.0023 (9)
O5	0.0251 (9)	0.0213 (7)	0.0283 (9)	−0.0018 (7)	0.0070 (8)	−0.0022 (7)
O6	0.0433 (12)	0.0332 (10)	0.0439 (11)	−0.0046 (9)	0.0128 (10)	−0.0138 (8)
O7	0.0336 (10)	0.0221 (8)	0.0283 (9)	0.0029 (7)	−0.0002 (8)	0.0025 (7)
O8	0.0837 (18)	0.0234 (9)	0.0542 (13)	−0.0053 (11)	−0.0061 (13)	0.0034 (9)
O9	0.0466 (12)	0.0302 (9)	0.0343 (10)	0.0134 (9)	−0.0038 (10)	−0.0072 (7)
O10	0.0699 (18)	0.0433 (12)	0.109 (2)	0.0250 (13)	−0.0303 (16)	−0.0047 (13)
O11	0.0628 (16)	0.0706 (15)	0.0365 (12)	−0.0076 (14)	0.0116 (11)	0.0106 (11)
O12	0.0476 (13)	0.0543 (13)	0.0511 (13)	−0.0148 (12)	0.0048 (11)	0.0135 (10)

Geometric parameters (Å, º) top

C1—O2	1.400 (3)	C13—H13	1.0000
C1—O1	1.414 (3)	C14—O11	1.404 (4)
C1—C2	1.522 (3)	C14—H14A	0.9800
C1—H1	1.0000	C14—H14B	0.9800
C2—O3	1.444 (3)	C14—H14C	0.9800
C2—C3	1.516 (3)	C15—O12	1.412 (4)
C2—H2	1.0000	C15—H15A	0.9800
C3—O5	1.449 (3)	C15—H15B	0.9800
C3—C4	1.516 (3)	C15—H15C	0.9800
C3—H3	1.0000	C16—O4	1.198 (3)
C4—O7	1.449 (3)	C16—O3	1.348 (3)
C4—C5	1.530 (3)	C16—C17	1.495 (3)
C4—H4	1.0000	C17—H17A	0.9800
C5—O1	1.433 (3)	C17—H17B	0.9800
C5—C6	1.500 (3)	C17—H17C	0.9800
C5—H5	1.0000	C18—O6	1.198 (3)
C6—O9	1.439 (3)	C18—O5	1.357 (3)
C6—H6A	0.9900	C18—C19	1.495 (4)
C6—H6B	0.9900	C19—H19A	0.9800
C7—C12	1.373 (4)	C19—H19B	0.9800
C7—C8	1.383 (4)	C19—H19C	0.9800
C7—O2	1.394 (3)	C20—O8	1.198 (3)
C8—C9	1.387 (4)	C20—O7	1.359 (3)
C8—H8	0.9500	C20—C21	1.483 (4)
C9—C10	1.397 (4)	C21—H21A	0.9800
C9—H9	0.9500	C21—H21B	0.9800
C10—C11	1.372 (4)	C21—H21C	0.9800
C10—C13	1.506 (4)	C22—O10	1.195 (4)
C11—C12	1.390 (4)	C22—O9	1.341 (3)
C11—H11	0.9500	C22—C23	1.482 (5)
C12—H12	0.9500	C23—H23A	0.9800
C13—O12	1.395 (4)	C23—H23B	0.9800
C13—O11	1.417 (4)	C23—H23C	0.9800

O2—C1—O1	107.73 (17)	O11—C13—H13	107.8
O2—C1—C2	107.29 (19)	C10—C13—H13	107.8
O1—C1—C2	109.94 (18)	O11—C14—H14A	109.5
O2—C1—H1	110.6	O11—C14—H14B	109.5
O1—C1—H1	110.6	H14A—C14—H14B	109.5
C2—C1—H1	110.6	O11—C14—H14C	109.5
O3—C2—C3	110.26 (18)	H14A—C14—H14C	109.5
O3—C2—C1	105.40 (17)	H14B—C14—H14C	109.5
C3—C2—C1	109.29 (19)	O12—C15—H15A	109.5
O3—C2—H2	110.6	O12—C15—H15B	109.5
C3—C2—H2	110.6	H15A—C15—H15B	109.5
C1—C2—H2	110.6	O12—C15—H15C	109.5
O5—C3—C4	106.76 (17)	H15A—C15—H15C	109.5
O5—C3—C2	109.66 (19)	H15B—C15—H15C	109.5
C4—C3—C2	110.31 (18)	O4—C16—O3	123.5 (2)
O5—C3—H3	110.0	O4—C16—C17	126.2 (3)
C4—C3—H3	110.0	O3—C16—C17	110.2 (2)
C2—C3—H3	110.0	C16—C17—H17A	109.5
O7—C4—C3	106.83 (17)	C16—C17—H17B	109.5
O7—C4—C5	108.2 (2)	H17A—C17—H17B	109.5
C3—C4—C5	110.31 (18)	C16—C17—H17C	109.5
O7—C4—H4	110.5	H17A—C17—H17C	109.5
C3—C4—H4	110.5	H17B—C17—H17C	109.5
C5—C4—H4	110.5	O6—C18—O5	124.0 (2)
O1—C5—C6	107.67 (18)	O6—C18—C19	125.5 (2)
O1—C5—C4	108.10 (19)	O5—C18—C19	110.4 (2)
C6—C5—C4	113.56 (19)	C18—C19—H19A	109.5
O1—C5—H5	109.1	C18—C19—H19B	109.5
C6—C5—H5	109.1	H19A—C19—H19B	109.5
C4—C5—H5	109.1	C18—C19—H19C	109.5
O9—C6—C5	108.3 (2)	H19A—C19—H19C	109.5
O9—C6—H6A	110.0	H19B—C19—H19C	109.5
C5—C6—H6A	110.0	O8—C20—O7	122.9 (2)
O9—C6—H6B	110.0	O8—C20—C21	126.2 (2)
C5—C6—H6B	110.0	O7—C20—C21	110.9 (2)
H6A—C6—H6B	108.4	C20—C21—H21A	109.5
C12—C7—C8	120.7 (2)	C20—C21—H21B	109.5
C12—C7—O2	123.8 (2)	H21A—C21—H21B	109.5
C8—C7—O2	115.5 (2)	C20—C21—H21C	109.5
C7—C8—C9	119.1 (3)	H21A—C21—H21C	109.5
C7—C8—H8	120.5	H21B—C21—H21C	109.5
C9—C8—H8	120.5	O10—C22—O9	123.0 (3)
C8—C9—C10	121.0 (2)	O10—C22—C23	125.4 (3)
C8—C9—H9	119.5	O9—C22—C23	111.6 (3)
C10—C9—H9	119.5	C22—C23—H23A	109.5
C11—C10—C9	118.2 (3)	C22—C23—H23B	109.5
C11—C10—C13	122.5 (3)	H23A—C23—H23B	109.5
C9—C10—C13	119.2 (2)	C22—C23—H23C	109.5
C10—C11—C12	121.5 (3)	H23A—C23—H23C	109.5
C10—C11—H11	119.3	H23B—C23—H23C	109.5
C12—C11—H11	119.3	C1—O1—C5	112.28 (16)
C7—C12—C11	119.4 (2)	C7—O2—C1	117.00 (19)
C7—C12—H12	120.3	C16—O3—C2	117.93 (19)
C11—C12—H12	120.3	C18—O5—C3	118.07 (18)
O12—C13—O11	111.7 (3)	C20—O7—C4	117.55 (19)
O12—C13—C10	108.7 (2)	C22—O9—C6	117.8 (2)
O11—C13—C10	113.0 (2)	C14—O11—C13	114.9 (2)
O12—C13—H13	107.8	C13—O12—C15	113.2 (3)

O2—C1—C2—O3	67.0 (2)	C11—C10—C13—O11	−121.4 (3)
O1—C1—C2—O3	−176.06 (17)	C9—C10—C13—O11	60.5 (4)
O2—C1—C2—C3	−174.46 (17)	O2—C1—O1—C5	−178.82 (18)
O1—C1—C2—C3	−57.6 (2)	C2—C1—O1—C5	64.6 (2)
O3—C2—C3—O5	−74.1 (2)	C6—C5—O1—C1	173.20 (19)
C1—C2—C3—O5	170.47 (17)	C4—C5—O1—C1	−63.7 (2)
O3—C2—C3—C4	168.59 (18)	C12—C7—O2—C1	−4.1 (3)
C1—C2—C3—C4	53.2 (2)	C8—C7—O2—C1	175.4 (2)
O5—C3—C4—O7	69.5 (2)	O1—C1—O2—C7	76.8 (2)
C2—C3—C4—O7	−171.43 (18)	C2—C1—O2—C7	−164.91 (18)
O5—C3—C4—C5	−173.12 (18)	O4—C16—O3—C2	−3.5 (4)
C2—C3—C4—C5	−54.0 (3)	C17—C16—O3—C2	176.82 (19)
O7—C4—C5—O1	174.03 (16)	C3—C2—O3—C16	101.6 (2)
C3—C4—C5—O1	57.5 (2)	C1—C2—O3—C16	−140.5 (2)
O7—C4—C5—C6	−66.6 (2)	O6—C18—O5—C3	0.7 (3)
C3—C4—C5—C6	176.9 (2)	C19—C18—O5—C3	−178.8 (2)
O1—C5—C6—O9	60.3 (2)	C4—C3—O5—C18	−143.3 (2)
C4—C5—C6—O9	−59.4 (3)	C2—C3—O5—C18	97.2 (2)
C12—C7—C8—C9	−1.2 (4)	O8—C20—O7—C4	−2.4 (4)
O2—C7—C8—C9	179.4 (2)	C21—C20—O7—C4	177.8 (2)
C7—C8—C9—C10	−0.4 (4)	C3—C4—O7—C20	−135.4 (2)
C8—C9—C10—C11	2.7 (4)	C5—C4—O7—C20	105.8 (2)
C8—C9—C10—C13	−179.2 (3)	O10—C22—O9—C6	6.9 (5)
C9—C10—C11—C12	−3.5 (4)	C23—C22—O9—C6	−173.9 (3)
C13—C10—C11—C12	178.5 (3)	C5—C6—O9—C22	148.1 (2)
C8—C7—C12—C11	0.4 (4)	O12—C13—O11—C14	−61.7 (3)
O2—C7—C12—C11	179.8 (2)	C10—C13—O11—C14	61.2 (4)
C10—C11—C12—C7	2.0 (4)	O11—C13—O12—C15	−69.5 (3)
C11—C10—C13—O12	3.2 (4)	C10—C13—O12—C15	165.2 (3)
C9—C10—C13—O12	−174.9 (3)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O11ⁱ	1.00	2.44	3.347 (3)	151
C12—H12···O4ⁱⁱ	0.95	2.45	3.321 (3)	152
C19—H19A···O3ⁱⁱⁱ	0.98	2.54	3.510 (3)	171
C19—H19C···O8^iv	0.98	2.49	3.414 (3)	157
C21—H21C···O10^iv	0.98	2.29	3.252 (4)	168
C23—H23C···Cg^v	0.98	2.71	3.615 (4)	153

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) x+1/2, −y+1/2, −z; (iv) x+1/2, −y+3/2, −z; (v) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₃H₃₀O₁₂
M_r	498.47
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	7.9004 (2), 10.9961 (3), 29.2289 (8)
V (Å³)	2539.22 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.45 × 0.32 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13406, 3493, 2644
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.102, 0.97
No. of reflections	3493
No. of parameters	322
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.20

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL99 (Keller, 1999), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O11ⁱ	1.00	2.44	3.347 (3)	151
C12—H12···O4ⁱⁱ	0.95	2.45	3.321 (3)	152
C19—H19A···O3ⁱⁱⁱ	0.98	2.54	3.510 (3)	171
C19—H19C···O8^iv	0.98	2.49	3.414 (3)	157
C21—H21C···O10^iv	0.98	2.29	3.252 (4)	168
C23—H23C···Cg^v	0.98	2.71	3.615 (4)	153

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) x+1/2, −y+1/2, −z; (iv) x+1/2, −y+3/2, −z; (v) x, y+1, z.

Acknowledgements

This work was supported by the National Research Foundation, Pretoria (NRF, GUN 2053652), the South African Research Chairs Initiative and the University of the Witwatersrand.

References

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