Two modes of O—H...O hydrogen bonding utilized in dimorphs of racemic 6-O-acryloyl-2-O-benzoyl-myo-inositol 1,3,5-orthoformate

The title compound, C₁₇H₁₆O₈, yields conformational di­morphs [forms (I) and (II)] at room temperature, separately or concomitantly, depending on the solvent of crystallization. The yield of crystals of form (I) is always much more than that of crystals of form (II). The mol­ecule has one donor –OH group that can make inter­molecular O—H...O hydrogen bonds with one of the two acceptor C=O groups, as well as with the hydroxyl O atom; inter­estingly, each of the options is utilized separately in the dimorphs. The crystal structure of form (I) contains one mol­ecule in the asymmetric unit and is organized as a planar sheet of centrosymmetric dimers via O—H...O hydrogen bonds involving the OH group and the carbonyl O atom of the acryloyl group. In the crystal structure of form (II), which contains two independent mol­ecules in the asymmetric unit, two different O—H...O hydrogen bonds, viz. hydroxyl–hydroxyl and hydroxyl–carbonyl (benzoyl), connect the mol­ecules in a layered arrangement. Another notable feature is the transformation of form (II) to form (I) via melt crystallization upon heating to 411 K. The higher yield of form (I) during crystallization and the thermal transition of form (II) to form (I) suggest that the association in form (I) is more highly favoured than that in form (II), which is valuable in understanding the priorities of mol­ecular aggregation during nucleation of various polymorphs.

S1. Comment

myo-Inositol 1,3,5-orthoester derivatives serve as key intermediates (Sureshan et al., 2003) for the preparation of biologically relevant myo-inositol phosphates, which play a significant role in cellular signal transduction pathways (Potter & Lampe, 1995). The title compound, (1), was synthesized to examine the acyl transfer reactivities in crystals of myo-inositol orthoester derivatives carrying different ester groups (Praveen et al.,1998; Sarmah et al., 2005; Murali et al., 2007). Here, we report the structures of dimorphs of (1), namely form (I) (plates) and form (II) (needles). The two sets of atom numbers for the C atoms of the inositol ring in the scheme below refer to the two enantiomers: anticlockwise numbering for the D configuration and clockwise numbering for the L configuration (Parthasarathy & Eisenberg, 1986).

Single-crystal X-ray intensity measurements for crystals of form (I) were recorded at ambient temperature (297 K), while data for crystals of form (II) were measured at 133 K to minimize the large thermal anisotropies observed for the phenyl ring atoms at room temperature. Crystals of form (I) are triclinic, space group P1 (Fig. 1), while form (II) crystallises in the noncentrosymmetric space group P2₁ with two independent molecules in the asymmetric unit having different chirality (Fig. 2). The two molecules in the crystal structure of form (II) show significant differences in the torsion angles associated with the three functional groups, namely C1—C2—O2—C8 (the benzoyl group), C1—C6—O6—C15 (the acryloyl group) and C3—C4—O4—H18 (the hydroxyl group). The torsion-angle difference for the benzoyl group is 20°, for the acryloyl group 15° and for the hydroxyl group 34° (Table 1). The molecular overlap of form (I) and molecule 1 of form (II) reveals major conformational changes in the hydroxyl groups and in the benzoyl groups (Fig. 3). The orientations of the hydroxyl groups are almost reversed (113°), whereas the benzoyl groups show a difference of ~52° in their torsion angles. The difference in the torsion angles of the acryloyl group (C1—C6—O6—C15) is 13°. These conformational changes in the three functional groups have a profound influence on the molecular association in the dimorphs.

The hydroxyl group forms different intermolecular O—H···O hydrogen bonds in the crystal structures of forms (I) and (II). In form (I), adjacent molecules form centrosymmetric dimers via O—H···O hydrogen bonds involving the OH group (O4—H18) and carbonyl atom O8 of the acryloyl group (Fig. 4). In form (II), the –OH groups of the two symmetry-independent molecules are involved in a hydrogen-bonding interaction (O4'—H18'···O4). The acceptor atom O4 also acts as a donor in a hydroxyl···carbonyl interaction (O4—H18···O7'), resulting in a catemeric arrangement along the c axis (Fig. 5). Additionally, five supporting C—H···O interactions (C1—H1···O5, C1'—H1'···O5', C3—H3···O7', C3'—H3'···O7 and C16—H16···O4') hold the molecules within the chain.

The hydrogen-bonded units thus formed make different three-dimensional patterns of molecular organization in the polymorphs. In form (I), O—H···O-linked centrosymmetric dimers form a planar structure. In form (II), each molecule in the asymmetric unit forms a dimer by aggregating sideways, bringing orthoformate groups closer via noncentrosymmetric C—H···O interactions (C7—H7···O8', C6—H6···O5' and C7'-H7'···O8) of comparable strength (Table 2). These dimeric units are are further joined via O4'—H18'···O4, C3'—H3'···O7 and C16—H16···O4' hydrogen-bonding interactions, thus forming a chain extending along the b axis. Neighbouring chains are weakly associated along the a axis via C12'—H12'···O8' and C13—H13···O3' contacts, thus forming a layered arrangement (Fig. 6).

A differential scanning calorimetry study of crystals of form (I) shows only a single endotherm at 426 K, while crystals of form (II) show two endothermic peaks. The first of these, at 411 K, was established by hot-stage microscopy to be the structural phase transition to form (I) via a molten phase. The second endotherm at 425 K corresponds to the melting of the crystals of form (I). While single-crystal to single-crystal thermal phase transitions have been reported earlier in myo-inositol derivatives (Steiner et al., 1993; Gonnade et al., 2005, 2008), in this instance the conversion of form (II) to form (I) occurs via melt crystallization, often observed amongst polymorphs of pharmaceutical crystals (Cosgrove et al., 2005; Wishkerman & Bernstein, 2006; Vega et al., 2006; Roy et al., 2007; Grooff et al., 2007). Thus, form (II) upon heating transforms irreversibly to form (I).

In conclusion, orientational changes in a small functional group like –OH (Ibberson et al., 2008) and the benzoyl group induce diverse hydrogen-bonding patterns in molecular associations and result in polymorphic modifications. The significantly higher yield of form (I) over form (II), and the irreversible transformation of form (II) to form (I), suggest a preference for a dimeric O—H···O hydrogen bond over a catemeric O—H···O hydrogen bond (Das & Desiraju, 2006) in nucleation and crystal growth.

S2. Experimental

Racemic 2-O-benzoyl-6-O-acryloyl-myo-inositol 1,3,5-orthoformate, (1), was prepared as follows. Freshly prepared acryloyl chloride (0.182 g, 2 mmol) was added to a cooled solution of the diol [Which diol?] (0.588 g, 2 mmol) and dry triethylamine (0.405 g, 6 mmol) in dry dimethylfomamide (DMF) (12 ml) and the reaction mixture was stirred at room temperature for 12 h. The DMF was evaporated under reduced pressure, and the residue was diluted with dichloromethane and washed with water, dilute HCl, saturated sodium bicarbonate solution and brine. The organic layer was dried with anhydrous sodium sulfate and concentrated, and the product purified by column chromatography to obtain (1) (yield 0.25 g, 36%). Spectroscopic analysis: λ_max (Nujol, cm^-1): 1728, 1701, 3444; ¹H NMR (200 MHz, CDCl₃, Me₄Si, δ, p.p.m.): 2.56–2.59 (1H, J = 6.1 Hz, d, OH), 4.43–4.49 (1H, m, Ins H), 4.50–4.57 (2H, m, Ins H), 4.63–4.74 (1H, m, Ins H), 5.52–5.55 (1H, J = 1.6 Hz, q, Ins H), 5.62 (1H, J = 1.3 Hz, d, Ins H), 5.66–5.71 (1H, J = 3.9 and 1.6 Hz, td, CH), 5.93–6.56 (3H, m, CH═ CH₂), 7.43–7.65 (3H, m, ArH), 8.13–8.19 (2H, m, Ar H); ¹³C NMR (125 MHz, CDCl₃, δ, p.p.m.): 63.3 (Ins C), 67.2 (Ins C), 68.1 (Ins C), 69.2 (Ins C), 71.5 (Ins C), 102.6 (O₃C), 126.9 (Ar C), 128.2 (Ar C, s), 129.2 (Ar C), 129.7 (Ar C, s), 132.7 (CH₂), 133.3 (═CH), 164.2 (C═ O), 166 (C═O).

Crystallization of (1) from ethyl acetate (containing only a trace of light petroleum) and from other common solvents (dichloromethane, toluene, methanol, tetrahydrofuran, chloroform and benzene) yielded exclusively plates [form (I), m.p. 421–423 K], whereas crystallization from an ethyl acetate–light petroleum mixture (1:1 v/v) produced needle-shaped crystals [form (II), m.p. 410–412 K]. Crystallization from a dichloromethane–light petroleum mixture yielded both forms concomitantly; the relative yield of crystals of form (II) was always much less than that of crystals of form (I). All the crystallization experiments were carried out under comparable conditions.

S3. Refinement

All H atoms (except hydroxyl H atoms) were placed in geometrically idealized positions for both forms. For form (I), C—H = 0.98 Å for the inositol ring H atoms and orthoformate H atom, and C—H = 0.93 Å for the aromatic and alkenyl H atoms. For form (II), C—H = 1.00 Å for the inositol ring H atoms and orthoformate H atom, and C—H = 0.95 Å for the aromatic and alkenyl H atoms. They were constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(C). The O-bound H atoms in both forms were located in difference Fourier maps and refined isotropically. The refined O—H distances were 0.95 (5) Å for form (I), and 0.82 (5) and 0.84 (6) Å for molecules 1 and 2, respectively, of form (II).

In the refinement of form (II), the data were merged using MERG4 in SHELXL97 (Sheldrick, 2008), according to the standard procedure for X-ray Mo Kα measurements of chemical compounds without heavy atoms. The E statistics and N (Z) test for form II confirmed the choice of the noncentrosymmetric space group P2₁.

Computing details

For both compounds, data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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 Mercury (Version 2.1; Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Version 6.14; Sheldrick, 2008) and PLATON (Spek, 2003).

Figures

	Fig. 1. The molecular structure of form (I) of (1) [(1S,3R,5S)-enantiomer], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 40% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The molecular structure of form (II) of (1) [molecules 1 and 2 have (1S,3R,5S) and (1R,3S,5R) configurations, respectively], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 40% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. Overlap diagram of molecules in form (I) and form (II).
	Fig. 4. The dimer formed by O—H···O hydrogen bonding in form (I). For the sake of clarity, H atoms not involved in hydrogen bonding have been omitted. [Symmetry code: (i) -x + 2, -y + 2, -z + 2]
	Fig. 5. Molecules linked via two different O—H···O hydrogen bonds and other weak C—H···O interactions in form (II), leading to a catemeric arrangement running parallel to the c axis. For the sake of clarity, H atoms not involved in hydrogen bonding have been omitted. [Symmetry codes: (i) x, y, z - 1; (ii) x, y, z + 1.]
	Fig. 6. The packing of molecules in the crystal structure of form (II). Dashed lines indicate intermolecular C—H···O and O—H···O interactions. For the sake of clarity, H atoms not involved in hydrogen bonding have been omitted. [Symmetry codes: (i) -x + 2, y + 1/2, -z + 2; (ii) -x + 2, y - 1/2, -z + 2; (iii) x - 1, y, z - 1; (iv) -x + 1, y + 1/2, -z + 1.]

(I) 6-O-acryloyl-2-O-benzoyl-myo-inositol 1,3,5-orthoformate

Crystal data

C17H16O8	Z = 2
Mr = 348.30	F(000) = 364
Triclinic, P1	Dx = 1.480 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8808 (6) Å	Cell parameters from 3975 reflections
b = 9.5502 (6) Å	θ = 2.4–27.1°
c = 9.7100 (6) Å	µ = 0.12 mm^−1
α = 102.266 (1)°	T = 297 K
β = 101.733 (1)°	Plate, colourless
γ = 94.334 (1)°	0.56 × 0.43 × 0.19 mm
V = 781.83 (9) Å^3

Data collection

Bruker Smart APEX CCD area-detector diffractometer	2755 independent reflections
Radiation source: fine-focus sealed tube	2374 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
ϕ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −10→10
Tmin = 0.936, Tmax = 0.978	k = −11→11
9163 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0828P)^2 + 0.3438P] where P = (Fo^2 + 2Fc^2)/3
2755 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.53850 (18)	0.68286 (17)	0.52944 (16)	0.0564 (4)
O2	0.37202 (16)	0.58168 (15)	0.72371 (17)	0.0496 (4)
O3	0.40799 (17)	0.85290 (18)	0.64395 (19)	0.0589 (5)
O4	0.6867 (2)	0.9262 (2)	0.98833 (18)	0.0657 (5)
O5	0.64770 (19)	0.92263 (18)	0.60408 (18)	0.0593 (5)
O6	0.84623 (16)	0.70840 (17)	0.84356 (18)	0.0538 (4)
O7	0.48886 (19)	0.41461 (19)	0.8209 (2)	0.0701 (6)
O8	1.0670 (2)	0.8405 (2)	0.8506 (2)	0.0772 (6)
C1	0.6147 (2)	0.6506 (2)	0.6613 (2)	0.0469 (5)
H1	0.6348	0.5495	0.6433	0.056*
C2	0.5157 (2)	0.6779 (2)	0.7715 (2)	0.0455 (5)
H2	0.5725	0.6658	0.8650	0.055*
C3	0.4744 (3)	0.8323 (2)	0.7859 (3)	0.0527 (6)
H3	0.4011	0.8502	0.8488	0.063*
C4	0.6215 (3)	0.9389 (2)	0.8467 (3)	0.0530 (6)
H4	0.5948	1.0372	0.8507	0.064*
C5	0.7288 (2)	0.9064 (2)	0.7444 (2)	0.0462 (5)
H5	0.8243	0.9742	0.7794	0.055*
C6	0.7679 (2)	0.7503 (2)	0.7159 (2)	0.0478 (5)
H6	0.8300	0.7355	0.6425	0.057*
C7	0.5085 (3)	0.8270 (3)	0.5527 (3)	0.0588 (6)
H7	0.4575	0.8437	0.4591	0.071*
C8	0.3743 (2)	0.4521 (2)	0.7575 (2)	0.0456 (5)
C9	0.2212 (2)	0.3629 (2)	0.7063 (2)	0.0437 (5)
C10	0.2135 (3)	0.2196 (2)	0.7166 (3)	0.0527 (6)
H10	0.3019	0.1836	0.7577	0.063*
C11	0.0740 (3)	0.1307 (3)	0.6654 (3)	0.0620 (6)
H11	0.0686	0.0348	0.6718	0.074*
C12	−0.0563 (3)	0.1837 (3)	0.6052 (3)	0.0632 (7)
H12	−0.1494	0.1232	0.5698	0.076*
C13	−0.0501 (3)	0.3265 (3)	0.5968 (3)	0.0617 (7)
H13	−0.1394	0.3620	0.5568	0.074*
C14	0.0881 (2)	0.4167 (3)	0.6475 (2)	0.0511 (5)
H14	0.0921	0.5130	0.6423	0.061*
C15	0.9953 (3)	0.7570 (2)	0.8983 (3)	0.0518 (5)
C16	1.0577 (3)	0.6937 (3)	1.0190 (3)	0.0603 (6)
H16	0.9902	0.6599	1.0697	0.072*
C17	1.2035 (3)	0.6832 (3)	1.0575 (4)	0.0777 (8)
H17A	1.2725	0.7166	1.0079	0.093*
H17B	1.2396	0.6424	1.1349	0.093*
H18	0.771 (5)	1.000 (5)	1.036 (5)	0.136 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0539 (9)	0.0553 (10)	0.0513 (9)	−0.0043 (7)	0.0015 (7)	0.0073 (7)
O2	0.0349 (8)	0.0459 (8)	0.0645 (9)	−0.0086 (6)	0.0013 (7)	0.0197 (7)
O3	0.0413 (8)	0.0559 (10)	0.0768 (11)	0.0037 (7)	0.0009 (8)	0.0222 (8)
O4	0.0733 (12)	0.0609 (11)	0.0522 (10)	−0.0086 (9)	0.0065 (8)	0.0030 (8)
O5	0.0542 (9)	0.0577 (10)	0.0627 (10)	−0.0097 (7)	−0.0001 (7)	0.0253 (8)
O6	0.0359 (8)	0.0527 (9)	0.0698 (10)	−0.0028 (6)	0.0006 (7)	0.0217 (7)
O7	0.0442 (9)	0.0663 (11)	0.0942 (13)	−0.0069 (8)	−0.0115 (9)	0.0371 (10)
O8	0.0453 (10)	0.0868 (14)	0.0962 (14)	−0.0141 (9)	−0.0026 (9)	0.0397 (11)
C1	0.0417 (11)	0.0398 (11)	0.0522 (12)	−0.0026 (9)	0.0033 (9)	0.0049 (9)
C2	0.0344 (10)	0.0439 (11)	0.0528 (12)	−0.0084 (8)	0.0006 (9)	0.0130 (9)
C3	0.0418 (12)	0.0464 (12)	0.0651 (14)	−0.0013 (9)	0.0094 (10)	0.0073 (10)
C4	0.0512 (13)	0.0395 (11)	0.0608 (14)	−0.0028 (9)	0.0060 (10)	0.0046 (10)
C5	0.0396 (11)	0.0404 (11)	0.0531 (12)	−0.0082 (8)	0.0004 (9)	0.0134 (9)
C6	0.0390 (11)	0.0481 (12)	0.0527 (12)	−0.0031 (9)	0.0062 (9)	0.0111 (9)
C7	0.0530 (13)	0.0568 (14)	0.0589 (14)	−0.0066 (11)	−0.0064 (11)	0.0196 (11)
C8	0.0390 (11)	0.0475 (12)	0.0485 (11)	−0.0024 (9)	0.0044 (9)	0.0156 (9)
C9	0.0397 (11)	0.0475 (12)	0.0426 (11)	−0.0049 (9)	0.0070 (8)	0.0138 (9)
C10	0.0488 (13)	0.0517 (13)	0.0594 (13)	−0.0013 (10)	0.0095 (10)	0.0216 (10)
C11	0.0649 (16)	0.0475 (13)	0.0707 (15)	−0.0145 (11)	0.0134 (12)	0.0167 (11)
C12	0.0487 (13)	0.0689 (16)	0.0648 (15)	−0.0219 (11)	0.0051 (11)	0.0177 (12)
C13	0.0394 (12)	0.0769 (17)	0.0672 (15)	−0.0069 (11)	0.0014 (11)	0.0282 (13)
C14	0.0427 (12)	0.0519 (12)	0.0597 (13)	−0.0029 (9)	0.0066 (10)	0.0226 (10)
C15	0.0396 (11)	0.0446 (12)	0.0662 (14)	−0.0018 (9)	0.0059 (10)	0.0104 (10)
C16	0.0461 (13)	0.0619 (15)	0.0682 (15)	0.0020 (11)	0.0023 (11)	0.0165 (12)
C17	0.0562 (16)	0.0781 (19)	0.094 (2)	0.0108 (13)	−0.0010 (14)	0.0262 (16)

Geometric parameters (Å, º)

O1—C7	1.402 (3)	C4—H4	0.9800
O1—C1	1.428 (3)	C5—C6	1.537 (3)
O2—C8	1.346 (2)	C5—H5	0.9800
O2—C2	1.445 (2)	C6—H6	0.9800
O3—C7	1.380 (3)	C7—H7	0.9800
O3—C3	1.445 (3)	C8—C9	1.481 (3)
O4—C4	1.414 (3)	C9—C14	1.389 (3)
O4—H18	0.95 (5)	C9—C10	1.390 (3)
O5—C7	1.413 (3)	C10—C11	1.384 (3)
O5—C5	1.451 (3)	C10—H10	0.9300
O6—C15	1.329 (3)	C11—C12	1.369 (4)
O6—C6	1.443 (3)	C11—H11	0.9300
O7—C8	1.199 (3)	C12—C13	1.381 (4)
O8—C15	1.207 (3)	C12—H12	0.9300
C1—C2	1.512 (3)	C13—C14	1.380 (3)
C1—C6	1.528 (3)	C13—H13	0.9300
C1—H1	0.9800	C14—H14	0.9300
C2—C3	1.531 (3)	C15—C16	1.461 (3)
C2—H2	0.9800	C16—C17	1.290 (4)
C3—C4	1.524 (3)	C16—H16	0.9300
C3—H3	0.9800	C17—H17A	0.9300
C4—C5	1.513 (3)	C17—H17B	0.9300
C7—O1—C1	110.89 (16)	O6—C6—H6	109.9
C8—O2—C2	116.56 (15)	C1—C6—H6	109.9
C7—O3—C3	111.51 (17)	C5—C6—H6	109.9
C4—O4—H18	112 (3)	O3—C7—O1	111.01 (19)
C7—O5—C5	110.88 (16)	O3—C7—O5	111.9 (2)
C15—O6—C6	118.78 (17)	O1—C7—O5	111.02 (19)
O1—C1—C2	110.08 (17)	O3—C7—H7	107.6
O1—C1—C6	107.00 (17)	O1—C7—H7	107.6
C2—C1—C6	110.04 (17)	O5—C7—H7	107.6
O1—C1—H1	109.9	O7—C8—O2	122.97 (19)
C2—C1—H1	109.9	O7—C8—C9	124.61 (19)
C6—C1—H1	109.9	O2—C8—C9	112.41 (17)
O2—C2—C1	110.92 (17)	C14—C9—C10	119.83 (19)
O2—C2—C3	107.37 (16)	C14—C9—C8	122.42 (19)
C1—C2—C3	108.23 (18)	C10—C9—C8	117.74 (19)
O2—C2—H2	110.1	C11—C10—C9	119.8 (2)
C1—C2—H2	110.1	C11—C10—H10	120.1
C3—C2—H2	110.1	C9—C10—H10	120.1
O3—C3—C4	107.09 (18)	C12—C11—C10	120.1 (2)
O3—C3—C2	109.12 (18)	C12—C11—H11	119.9
C4—C3—C2	109.51 (18)	C10—C11—H11	119.9
O3—C3—H3	110.4	C11—C12—C13	120.4 (2)
C4—C3—H3	110.4	C11—C12—H12	119.8
C2—C3—H3	110.4	C13—C12—H12	119.8
O4—C4—C5	113.09 (19)	C14—C13—C12	120.2 (2)
O4—C4—C3	108.84 (19)	C14—C13—H13	119.9
C5—C4—C3	107.77 (18)	C12—C13—H13	119.9
O4—C4—H4	109.0	C13—C14—C9	119.7 (2)
C5—C4—H4	109.0	C13—C14—H14	120.2
C3—C4—H4	109.0	C9—C14—H14	120.2
O5—C5—C4	107.28 (17)	O8—C15—O6	123.1 (2)
O5—C5—C6	104.45 (17)	O8—C15—C16	125.9 (2)
C4—C5—C6	114.75 (17)	O6—C15—C16	110.95 (19)
O5—C5—H5	110.0	C17—C16—C15	122.1 (3)
C4—C5—H5	110.0	C17—C16—H16	119.0
C6—C5—H5	110.0	C15—C16—H16	119.0
O6—C6—C1	105.53 (16)	C16—C17—H17A	120.0
O6—C6—C5	114.10 (17)	C16—C17—H17B	120.0
C1—C6—C5	107.40 (17)	H17A—C17—H17B	120.0
C7—O1—C1—C2	58.8 (2)	O5—C5—C6—O6	−178.26 (15)
C7—O1—C1—C6	−60.8 (2)	C4—C5—C6—O6	−61.1 (2)
C8—O2—C2—C1	87.3 (2)	O5—C5—C6—C1	−61.7 (2)
C8—O2—C2—C3	−154.63 (19)	C4—C5—C6—C1	55.5 (2)
O1—C1—C2—O2	64.0 (2)	C3—O3—C7—O1	63.1 (2)
C6—C1—C2—O2	−178.33 (16)	C3—O3—C7—O5	−61.5 (2)
O1—C1—C2—C3	−53.6 (2)	C1—O1—C7—O3	−63.2 (2)
C6—C1—C2—C3	64.1 (2)	C1—O1—C7—O5	61.9 (2)
C7—O3—C3—C4	60.4 (2)	C5—O5—C7—O3	60.9 (2)
C7—O3—C3—C2	−58.1 (2)	C5—O5—C7—O1	−63.7 (2)
O2—C2—C3—O3	−67.2 (2)	C2—O2—C8—O7	−1.6 (3)
C1—C2—C3—O3	52.6 (2)	C2—O2—C8—C9	178.90 (17)
O2—C2—C3—C4	175.88 (17)	O7—C8—C9—C14	172.7 (2)
C1—C2—C3—C4	−64.3 (2)	O2—C8—C9—C14	−7.8 (3)
O3—C3—C4—O4	177.61 (17)	O7—C8—C9—C10	−8.3 (3)
C2—C3—C4—O4	−64.2 (2)	O2—C8—C9—C10	171.18 (19)
O3—C3—C4—C5	−59.4 (2)	C14—C9—C10—C11	1.3 (3)
C2—C3—C4—C5	58.8 (2)	C8—C9—C10—C11	−177.7 (2)
C7—O5—C5—C4	−59.5 (2)	C9—C10—C11—C12	−0.2 (4)
C7—O5—C5—C6	62.7 (2)	C10—C11—C12—C13	−0.8 (4)
O4—C4—C5—O5	179.72 (16)	C11—C12—C13—C14	0.8 (4)
C3—C4—C5—O5	59.4 (2)	C12—C13—C14—C9	0.3 (4)
O4—C4—C5—C6	64.2 (2)	C10—C9—C14—C13	−1.4 (3)
C3—C4—C5—C6	−56.2 (2)	C8—C9—C14—C13	177.6 (2)
C15—O6—C6—C1	166.90 (18)	C6—O6—C15—O8	3.8 (3)
C15—O6—C6—C5	−75.4 (2)	C6—O6—C15—C16	−175.12 (19)
O1—C1—C6—O6	−176.31 (16)	O8—C15—C16—C17	−22.9 (4)
C2—C1—C6—O6	64.1 (2)	O6—C15—C16—C17	156.0 (3)
O1—C1—C6—C5	61.6 (2)	C3—C4—O4—H18	−172 (3)
C2—C1—C6—C5	−58.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H18···O8^i	0.95 (5)	1.98 (5)	2.930 (3)	174 (4)

Symmetry code: (i) −x+2, −y+2, −z+2.

(II) 6-O-acryloyl-2-O-benzoyl-myo-inositol 1,3,5-orthoformate

Crystal data

C17H16O8	F(000) = 728
Mr = 348.30	Dx = 1.463 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3573 reflections
a = 13.813 (4) Å	θ = 2.6–27.9°
b = 19.279 (5) Å	µ = 0.12 mm^−1
c = 5.9801 (15) Å	T = 133 K
β = 96.665 (4)°	Needle, colourless
V = 1581.8 (7) Å^3	0.19 × 0.12 × 0.05 mm
Z = 4

Data collection

Bruker Smart APEX CCD area-detector diffractometer	2870 independent reflections
Radiation source: fine-focus sealed tube	2669 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
ϕ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −16→16
Tmin = 0.978, Tmax = 0.994	k = −22→22
15127 measured reflections	l = −7→7

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0542P)^2 + 0.5516P] where P = (Fo^2 + 2Fc^2)/3
2870 reflections	(Δ/σ)max < 0.001
459 parameters	Δρmax = 0.29 e Å^−3
1 restraint	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.8125 (2)	0.47512 (15)	0.9305 (5)	0.0214 (7)
O2	0.6847 (2)	0.37656 (16)	0.6627 (5)	0.0228 (7)
O3	0.7345 (2)	0.39965 (15)	1.1492 (5)	0.0204 (6)
O4	0.8928 (2)	0.25283 (15)	1.0481 (5)	0.0219 (7)
O5	0.8950 (2)	0.43014 (15)	1.2587 (5)	0.0201 (7)
O6	0.9859 (2)	0.34782 (15)	0.7662 (5)	0.0199 (6)
O7	0.6789 (2)	0.27059 (16)	0.5052 (5)	0.0292 (8)
O8	1.1357 (2)	0.37660 (18)	0.9296 (5)	0.0298 (8)
C1	0.8457 (3)	0.4201 (2)	0.7955 (7)	0.0194 (9)
H1	0.8508	0.4372	0.6394	0.023*
C2	0.7763 (3)	0.3585 (2)	0.7881 (7)	0.0191 (9)
H2	0.8055	0.3183	0.7140	0.023*
C3	0.7632 (3)	0.3394 (2)	1.0299 (7)	0.0216 (9)
H3	0.7125	0.3024	1.0309	0.026*
C4	0.8602 (3)	0.3134 (2)	1.1506 (7)	0.0190 (9)
H4	0.8517	0.3028	1.3108	0.023*
C5	0.9345 (3)	0.3721 (2)	1.1456 (7)	0.0185 (9)
H5	0.9990	0.3580	1.2256	0.022*
C6	0.9459 (3)	0.3982 (2)	0.9075 (7)	0.0179 (9)
H6	0.9894	0.4398	0.9201	0.021*
C7	0.8047 (3)	0.4522 (2)	1.1506 (7)	0.0207 (10)
H7	0.7823	0.4923	1.2376	0.025*
C8	0.6432 (3)	0.3273 (2)	0.5226 (7)	0.0228 (10)
C9	0.5519 (3)	0.3507 (3)	0.3920 (7)	0.0257 (10)
C10	0.5079 (4)	0.3076 (3)	0.2251 (9)	0.0391 (13)
H10	0.5350	0.2633	0.2023	0.047*
C11	0.4248 (4)	0.3287 (4)	0.0914 (10)	0.0564 (18)
H11	0.3948	0.2988	−0.0224	0.068*
C12	0.3855 (4)	0.3927 (4)	0.1226 (10)	0.0558 (17)
H12	0.3288	0.4072	0.0289	0.067*
C13	0.4275 (4)	0.4359 (4)	0.2886 (11)	0.0524 (16)
H13	0.3990	0.4799	0.3113	0.063*
C14	0.5111 (4)	0.4158 (3)	0.4231 (9)	0.0381 (13)
H14	0.5407	0.4462	0.5362	0.046*
C15	1.0850 (3)	0.3449 (2)	0.7887 (7)	0.0191 (9)
C16	1.1199 (3)	0.2986 (2)	0.6175 (7)	0.0236 (10)
H16	1.0773	0.2651	0.5427	0.028*
C17	1.2100 (4)	0.3040 (3)	0.5695 (9)	0.0363 (12)
H17A	1.2525	0.3375	0.6445	0.044*
H17B	1.2327	0.2743	0.4598	0.044*
H18	0.847 (3)	0.226 (3)	1.058 (7)	0.018 (12)*
O1'	0.8180 (2)	−0.02353 (15)	0.4633 (5)	0.0214 (7)
O2'	0.7004 (2)	0.08949 (16)	0.2611 (5)	0.0239 (7)
O3'	0.7615 (2)	0.05067 (15)	0.7235 (5)	0.0194 (6)
O4'	0.9392 (2)	0.18745 (16)	0.6450 (5)	0.0224 (7)
O5'	0.9168 (2)	0.00484 (15)	0.7903 (5)	0.0197 (7)
O6'	0.9993 (2)	0.09656 (15)	0.3030 (5)	0.0198 (6)
O7'	0.7191 (2)	0.17852 (15)	0.0286 (5)	0.0208 (7)
O8'	1.1516 (2)	0.07692 (17)	0.4663 (5)	0.0262 (7)
C1'	0.8559 (3)	0.0326 (2)	0.3410 (7)	0.0208 (10)
H1'	0.8528	0.0203	0.1779	0.025*
C2'	0.7984 (3)	0.0984 (2)	0.3686 (7)	0.0192 (9)
H2'	0.8300	0.1382	0.2981	0.023*
C3'	0.7961 (3)	0.1123 (2)	0.6172 (7)	0.0189 (9)
H3'	0.7529	0.1528	0.6393	0.023*
C4'	0.8995 (3)	0.1260 (2)	0.7286 (7)	0.0184 (9)
H4'	0.8976	0.1314	0.8943	0.022*
C5'	0.9617 (3)	0.0630 (2)	0.6888 (7)	0.0185 (9)
H5'	1.0300	0.0698	0.7613	0.022*
C6'	0.9616 (3)	0.0434 (2)	0.4398 (7)	0.0200 (9)
H6'	0.9991	−0.0006	0.4276	0.024*
C7'	0.8209 (3)	−0.0061 (2)	0.6930 (7)	0.0194 (9)
H7'	0.7946	−0.0465	0.7715	0.023*
C8'	0.6696 (3)	0.1330 (2)	0.0917 (7)	0.0193 (9)
C9'	0.5686 (3)	0.1186 (2)	−0.0084 (7)	0.0239 (10)
C10'	0.5339 (3)	0.1548 (2)	−0.2026 (8)	0.0292 (11)
H10'	0.5745	0.1879	−0.2640	0.035*
C11'	0.4413 (4)	0.1430 (3)	−0.3055 (9)	0.0422 (14)
H11'	0.4180	0.1674	−0.4390	0.051*
C12'	0.3824 (4)	0.0957 (3)	−0.2142 (11)	0.0535 (17)
H12'	0.3183	0.0874	−0.2851	0.064*
C13'	0.4161 (4)	0.0602 (4)	−0.0204 (11)	0.0571 (18)
H13'	0.3746	0.0282	0.0428	0.069*
C14'	0.5098 (4)	0.0708 (3)	0.0825 (9)	0.0410 (13)
H14'	0.5334	0.0456	0.2142	0.049*
C15'	1.0961 (3)	0.1069 (2)	0.3299 (7)	0.0202 (9)
C16'	1.1229 (3)	0.1595 (2)	0.1670 (8)	0.0255 (10)
H16'	1.0734	0.1869	0.0868	0.031*
C17'	1.2132 (4)	0.1687 (3)	0.1320 (10)	0.0447 (14)
H17C	1.2632	0.1414	0.2114	0.054*
H17D	1.2291	0.2026	0.0270	0.054*
H18'	0.926 (4)	0.219 (3)	0.733 (9)	0.031 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0274 (16)	0.0169 (16)	0.0199 (15)	0.0032 (13)	0.0030 (13)	0.0013 (12)
O2	0.0198 (15)	0.0247 (16)	0.0231 (16)	0.0015 (13)	−0.0010 (12)	−0.0067 (13)
O3	0.0213 (15)	0.0199 (15)	0.0210 (15)	−0.0006 (12)	0.0072 (12)	−0.0009 (13)
O4	0.0256 (17)	0.0132 (15)	0.0277 (17)	−0.0049 (13)	0.0076 (13)	0.0011 (12)
O5	0.0241 (16)	0.0194 (15)	0.0170 (14)	0.0003 (13)	0.0038 (12)	−0.0054 (12)
O6	0.0234 (16)	0.0213 (16)	0.0157 (14)	−0.0036 (13)	0.0050 (12)	−0.0034 (12)
O7	0.0347 (19)	0.0178 (17)	0.0334 (18)	−0.0020 (14)	−0.0036 (15)	0.0007 (14)
O8	0.0217 (16)	0.0364 (19)	0.0309 (18)	−0.0009 (15)	0.0009 (14)	−0.0088 (15)
C1	0.025 (2)	0.020 (2)	0.015 (2)	0.0001 (19)	0.0074 (17)	0.0010 (17)
C2	0.015 (2)	0.021 (2)	0.022 (2)	−0.0017 (17)	0.0024 (16)	−0.0034 (18)
C3	0.025 (2)	0.018 (2)	0.023 (2)	−0.0031 (18)	0.0091 (18)	0.0004 (18)
C4	0.025 (2)	0.018 (2)	0.016 (2)	0.0015 (18)	0.0081 (17)	−0.0007 (17)
C5	0.016 (2)	0.020 (2)	0.020 (2)	0.0014 (18)	0.0039 (16)	−0.0018 (17)
C6	0.019 (2)	0.017 (2)	0.018 (2)	−0.0067 (17)	0.0026 (16)	−0.0016 (17)
C7	0.024 (2)	0.020 (2)	0.017 (2)	−0.0003 (18)	0.0007 (17)	−0.0042 (17)
C8	0.023 (2)	0.026 (3)	0.020 (2)	−0.010 (2)	0.0069 (18)	0.0011 (19)
C9	0.020 (2)	0.033 (3)	0.025 (2)	−0.0062 (19)	0.0069 (18)	−0.002 (2)
C10	0.025 (3)	0.051 (3)	0.039 (3)	−0.004 (2)	−0.004 (2)	−0.014 (3)
C11	0.034 (3)	0.082 (5)	0.048 (4)	0.003 (3)	−0.014 (3)	−0.033 (3)
C12	0.028 (3)	0.085 (5)	0.051 (4)	0.018 (3)	−0.012 (3)	−0.015 (3)
C13	0.032 (3)	0.061 (4)	0.062 (4)	0.018 (3)	−0.008 (3)	−0.017 (3)
C14	0.028 (3)	0.043 (3)	0.041 (3)	0.008 (2)	−0.006 (2)	−0.013 (2)
C15	0.020 (2)	0.018 (2)	0.020 (2)	−0.0029 (18)	0.0032 (18)	0.0037 (18)
C16	0.024 (2)	0.021 (2)	0.025 (2)	−0.0011 (19)	0.0009 (18)	−0.0024 (19)
C17	0.032 (3)	0.036 (3)	0.041 (3)	0.000 (2)	0.009 (2)	−0.013 (2)
O1'	0.0284 (17)	0.0197 (16)	0.0161 (15)	−0.0060 (13)	0.0019 (13)	−0.0015 (12)
O2'	0.0193 (15)	0.0269 (17)	0.0248 (16)	−0.0027 (13)	−0.0007 (12)	0.0103 (13)
O3'	0.0209 (15)	0.0187 (15)	0.0191 (15)	0.0006 (12)	0.0038 (12)	0.0034 (12)
O4'	0.0280 (17)	0.0155 (16)	0.0242 (17)	−0.0036 (13)	0.0052 (13)	−0.0007 (13)
O5'	0.0219 (16)	0.0168 (15)	0.0204 (15)	−0.0008 (12)	0.0027 (12)	0.0052 (12)
O6'	0.0185 (15)	0.0246 (16)	0.0159 (14)	−0.0014 (13)	0.0007 (11)	0.0026 (13)
O7'	0.0212 (15)	0.0159 (15)	0.0248 (16)	−0.0036 (13)	0.0000 (12)	0.0052 (12)
O8'	0.0216 (16)	0.0293 (18)	0.0274 (16)	0.0002 (14)	0.0019 (13)	0.0038 (14)
C1'	0.029 (2)	0.017 (2)	0.016 (2)	−0.0056 (18)	0.0021 (18)	0.0024 (17)
C2'	0.020 (2)	0.018 (2)	0.018 (2)	−0.0044 (18)	−0.0015 (17)	0.0068 (17)
C3'	0.022 (2)	0.013 (2)	0.022 (2)	0.0019 (17)	0.0055 (17)	0.0016 (17)
C4'	0.024 (2)	0.016 (2)	0.015 (2)	−0.0013 (18)	0.0044 (17)	−0.0018 (17)
C5'	0.018 (2)	0.018 (2)	0.019 (2)	−0.0009 (17)	0.0011 (17)	0.0039 (17)
C6'	0.026 (2)	0.016 (2)	0.018 (2)	0.0005 (18)	0.0055 (17)	0.0012 (17)
C7'	0.023 (2)	0.017 (2)	0.018 (2)	−0.0028 (18)	0.0034 (18)	0.0015 (17)
C8'	0.025 (2)	0.015 (2)	0.019 (2)	−0.0008 (18)	0.0093 (18)	−0.0008 (18)
C9'	0.024 (2)	0.023 (2)	0.024 (2)	0.0040 (18)	−0.0004 (18)	−0.0032 (19)
C10'	0.025 (3)	0.028 (3)	0.033 (3)	−0.001 (2)	−0.003 (2)	0.008 (2)
C11'	0.035 (3)	0.047 (3)	0.040 (3)	−0.006 (3)	−0.011 (2)	0.015 (3)
C12'	0.028 (3)	0.063 (4)	0.064 (4)	−0.016 (3)	−0.017 (3)	0.010 (3)
C13'	0.034 (3)	0.065 (4)	0.069 (4)	−0.023 (3)	−0.011 (3)	0.030 (4)
C14'	0.028 (3)	0.046 (3)	0.046 (3)	−0.011 (2)	−0.005 (2)	0.018 (3)
C15'	0.020 (2)	0.023 (2)	0.017 (2)	0.0041 (19)	0.0019 (18)	−0.0032 (18)
C16'	0.025 (2)	0.027 (3)	0.023 (2)	−0.0031 (19)	−0.0026 (19)	−0.0006 (19)
C17'	0.038 (3)	0.056 (4)	0.041 (3)	−0.003 (3)	0.008 (2)	0.014 (3)

Geometric parameters (Å, º)

C1—O1	1.440 (5)	C1'—O1'	1.438 (5)
C1—C2	1.524 (6)	C1'—C2'	1.516 (6)
C1—C6	1.525 (6)	C1'—C6'	1.524 (6)
C1—H1	1.0000	C1'—H1'	1.0000
C2—O2	1.437 (5)	C2'—O2'	1.440 (5)
C2—C3	1.523 (6)	C2'—C3'	1.515 (6)
C2—H2	1.0000	C2'—H2'	1.0000
C3—O3	1.442 (5)	C3'—O3'	1.454 (5)
C3—C4	1.531 (6)	C3'—C4'	1.528 (6)
C3—H3	1.0000	C3'—H3'	1.0000
C4—O4	1.416 (5)	C4'—O4'	1.420 (5)
C4—C5	1.530 (6)	C4'—C5'	1.523 (6)
C4—H4	1.0000	C4'—H4'	1.0000
C5—O5	1.446 (5)	C5'—O5'	1.448 (5)
C5—C6	1.536 (6)	C5'—C6'	1.536 (6)
C5—H5	1.0000	C5'—H5'	1.0000
C6—O6	1.439 (5)	C6'—O6'	1.446 (5)
C6—H6	1.0000	C6'—H6'	1.0000
C7—O3	1.401 (5)	C7'—O3'	1.392 (5)
C7—O5	1.403 (5)	C7'—O5'	1.400 (5)
C7—O1	1.405 (5)	C7'—O1'	1.410 (5)
C7—H7	1.0000	C7'—H7'	1.0000
C8—O7	1.209 (6)	C8'—O7'	1.199 (5)
C8—O2	1.349 (5)	C8'—O2'	1.346 (5)
C8—C9	1.475 (6)	C8'—C9'	1.480 (6)
C9—C10	1.383 (7)	C9'—C14'	1.380 (7)
C9—C14	1.398 (7)	C9'—C10'	1.392 (6)
C10—C11	1.382 (7)	C10'—C11'	1.372 (7)
C10—H10	0.9500	C10'—H10'	0.9500
C11—C12	1.369 (9)	C11'—C12'	1.377 (8)
C11—H11	0.9500	C11'—H11'	0.9500
C12—C13	1.373 (8)	C12'—C13'	1.379 (8)
C12—H12	0.9500	C12'—H12'	0.9500
C13—C14	1.384 (7)	C13'—C14'	1.383 (7)
C13—H13	0.9500	C13'—H13'	0.9500
C14—H14	0.9500	C14'—H14'	0.9500
C15—O8	1.198 (5)	C15'—O8'	1.201 (5)
C15—O6	1.360 (5)	C15'—O6'	1.343 (5)
C15—C16	1.481 (6)	C15'—C16'	1.483 (6)
C16—C17	1.313 (7)	C16'—C17'	1.300 (7)
C16—H16	0.9500	C16'—H16'	0.9500
C17—H17A	0.9500	C17'—H17C	0.9500
C17—H17B	0.9500	C17'—H17D	0.9500
O4—H18	0.82 (5)	O4'—H18'	0.84 (6)
O1—C1—C2	110.5 (3)	O2'—C2'—C3'	109.4 (3)
O1—C1—C6	106.8 (3)	O2'—C2'—C1'	109.2 (3)
C2—C1—C6	109.4 (3)	C3'—C2'—C1'	109.1 (3)
O1—C1—H1	110.0	O2'—C2'—H2'	109.7
C2—C1—H1	110.0	C3'—C2'—H2'	109.7
C6—C1—H1	110.0	C1'—C2'—H2'	109.7
O2—C2—C3	111.1 (3)	O3'—C3'—C2'	109.2 (3)
O2—C2—C1	109.8 (3)	O3'—C3'—C4'	106.7 (3)
C3—C2—C1	107.7 (3)	C2'—C3'—C4'	109.4 (3)
O2—C2—H2	109.4	O3'—C3'—H3'	110.5
C3—C2—H2	109.4	C2'—C3'—H3'	110.5
C1—C2—H2	109.4	C4'—C3'—H3'	110.5
O3—C3—C2	110.2 (3)	O4'—C4'—C5'	111.3 (3)
O3—C3—C4	107.8 (3)	O4'—C4'—C3'	111.7 (3)
C2—C3—C4	109.4 (3)	C5'—C4'—C3'	108.1 (3)
O3—C3—H3	109.8	O4'—C4'—H4'	108.6
C2—C3—H3	109.8	C5'—C4'—H4'	108.6
C4—C3—H3	109.8	C3'—C4'—H4'	108.6
O4—C4—C5	110.7 (3)	O5'—C5'—C4'	106.0 (3)
O4—C4—C3	111.8 (3)	O5'—C5'—C6'	105.3 (3)
C5—C4—C3	107.5 (3)	C4'—C5'—C6'	114.3 (3)
O4—C4—H4	108.9	O5'—C5'—H5'	110.4
C5—C4—H4	108.9	C4'—C5'—H5'	110.4
C3—C4—H4	108.9	C6'—C5'—H5'	110.4
O5—C5—C4	105.9 (3)	O6'—C6'—C1'	105.6 (3)
O5—C5—C6	105.4 (3)	O6'—C6'—C5'	114.5 (3)
C4—C5—C6	113.7 (3)	C1'—C6'—C5'	107.6 (3)
O5—C5—H5	110.6	O6'—C6'—H6'	109.7
C4—C5—H5	110.6	C1'—C6'—H6'	109.7
C6—C5—H5	110.6	C5'—C6'—H6'	109.7
O6—C6—C1	108.7 (3)	O3'—C7'—O5'	111.8 (3)
O6—C6—C5	114.3 (3)	O3'—C7'—O1'	111.4 (3)
C1—C6—C5	108.2 (3)	O5'—C7'—O1'	111.1 (3)
O6—C6—H6	108.5	O3'—C7'—H7'	107.5
C1—C6—H6	108.5	O5'—C7'—H7'	107.5
C5—C6—H6	108.5	O1'—C7'—H7'	107.5
O3—C7—O5	111.2 (3)	O7'—C8'—O2'	123.4 (4)
O3—C7—O1	110.5 (3)	O7'—C8'—C9'	123.8 (4)
O5—C7—O1	111.5 (3)	O2'—C8'—C9'	112.8 (4)
O3—C7—H7	107.8	C14'—C9'—C10'	120.1 (4)
O5—C7—H7	107.8	C14'—C9'—C8'	122.5 (4)
O1—C7—H7	107.8	C10'—C9'—C8'	117.4 (4)
O7—C8—O2	122.8 (4)	C11'—C10'—C9'	120.2 (5)
O7—C8—C9	124.2 (4)	C11'—C10'—H10'	119.9
O2—C8—C9	112.9 (4)	C9'—C10'—H10'	119.9
C10—C9—C14	119.0 (5)	C10'—C11'—C12'	119.7 (5)
C10—C9—C8	118.4 (4)	C10'—C11'—H11'	120.2
C14—C9—C8	122.5 (4)	C12'—C11'—H11'	120.2
C11—C10—C9	120.5 (5)	C11'—C12'—C13'	120.3 (5)
C11—C10—H10	119.8	C11'—C12'—H12'	119.8
C9—C10—H10	119.8	C13'—C12'—H12'	119.8
C12—C11—C10	120.1 (5)	C12'—C13'—C14'	120.5 (5)
C12—C11—H11	119.9	C12'—C13'—H13'	119.8
C10—C11—H11	119.9	C14'—C13'—H13'	119.8
C11—C12—C13	120.3 (5)	C9'—C14'—C13'	119.1 (5)
C11—C12—H12	119.8	C9'—C14'—H14'	120.4
C13—C12—H12	119.8	C13'—C14'—H14'	120.4
C12—C13—C14	120.3 (6)	O8'—C15'—O6'	123.9 (4)
C12—C13—H13	119.9	O8'—C15'—C16'	125.9 (4)
C14—C13—H13	119.9	O6'—C15'—C16'	110.1 (3)
C13—C14—C9	119.8 (5)	C17'—C16'—C15'	121.1 (5)
C13—C14—H14	120.1	C17'—C16'—H16'	119.5
C9—C14—H14	120.1	C15'—C16'—H16'	119.5
O8—C15—O6	123.2 (4)	C16'—C17'—H17C	120.0
O8—C15—C16	125.6 (4)	C16'—C17'—H17D	120.0
O6—C15—C16	111.2 (3)	H17C—C17'—H17D	120.0
C17—C16—C15	119.8 (4)	C7—O1—C1	111.0 (3)
C17—C16—H16	120.1	C8—O2—C2	116.0 (3)
C15—C16—H16	120.1	C7—O3—C3	110.8 (3)
C16—C17—H17A	120.0	C4—O4—H18	102 (3)
C16—C17—H17B	120.0	C7—O5—C5	112.5 (3)
H17A—C17—H17B	120.0	C15—O6—C6	114.8 (3)
O1'—C1'—C2'	110.4 (3)	C7'—O1'—C1'	110.2 (3)
O1'—C1'—C6'	107.1 (3)	C8'—O2'—C2'	117.4 (3)
C2'—C1'—C6'	109.5 (3)	C7'—O3'—C3'	110.9 (3)
O1'—C1'—H1'	109.9	C4'—O4'—H18'	106 (4)
C2'—C1'—H1'	109.9	C7'—O5'—C5'	111.9 (3)
C6'—C1'—H1'	109.9	C15'—O6'—C6'	117.2 (3)
O1—C1—C2—O2	68.4 (4)	C4'—C5'—C6'—O6'	61.1 (5)
C6—C1—C2—O2	−174.2 (3)	O5'—C5'—C6'—C1'	59.9 (4)
O1—C1—C2—C3	−52.6 (4)	C4'—C5'—C6'—C1'	−56.0 (4)
C6—C1—C2—C3	64.8 (4)	O7'—C8'—C9'—C14'	−172.9 (5)
O2—C2—C3—O3	−67.3 (4)	O2'—C8'—C9'—C14'	7.3 (6)
C1—C2—C3—O3	52.9 (4)	O7'—C8'—C9'—C10'	7.6 (7)
O2—C2—C3—C4	174.2 (3)	O2'—C8'—C9'—C10'	−172.2 (4)
C1—C2—C3—C4	−65.5 (4)	C14'—C9'—C10'—C11'	−0.5 (7)
O3—C3—C4—O4	178.4 (3)	C8'—C9'—C10'—C11'	179.1 (5)
C2—C3—C4—O4	−61.8 (4)	C9'—C10'—C11'—C12'	0.8 (9)
O3—C3—C4—C5	−60.0 (4)	C10'—C11'—C12'—C13'	0.0 (10)
C2—C3—C4—C5	59.9 (4)	C11'—C12'—C13'—C14'	−1.1 (11)
O4—C4—C5—O5	−178.6 (3)	C10'—C9'—C14'—C13'	−0.6 (8)
C3—C4—C5—O5	59.1 (4)	C8'—C9'—C14'—C13'	179.9 (5)
O4—C4—C5—C6	66.2 (4)	C12'—C13'—C14'—C9'	1.4 (10)
C3—C4—C5—C6	−56.1 (4)	O8'—C15'—C16'—C17'	12.5 (7)
O1—C1—C6—O6	−174.6 (3)	O6'—C15'—C16'—C17'	−167.0 (5)
C2—C1—C6—O6	65.8 (4)	O3—C7—O1—C1	−63.1 (4)
O1—C1—C6—C5	60.9 (4)	O5—C7—O1—C1	61.1 (4)
C2—C1—C6—C5	−58.8 (4)	C2—C1—O1—C7	58.3 (4)
O5—C5—C6—O6	179.2 (3)	C6—C1—O1—C7	−60.7 (4)
C4—C5—C6—O6	−65.3 (4)	O7—C8—O2—C2	1.6 (6)
O5—C5—C6—C1	−59.6 (4)	C9—C8—O2—C2	−177.3 (3)
C4—C5—C6—C1	55.9 (4)	C3—C2—O2—C8	−102.0 (4)
O7—C8—C9—C10	−5.7 (7)	C1—C2—O2—C8	139.0 (4)
O2—C8—C9—C10	173.2 (4)	O5—C7—O3—C3	−60.8 (4)
O7—C8—C9—C14	177.5 (5)	O1—C7—O3—C3	63.6 (4)
O2—C8—C9—C14	−3.6 (6)	C2—C3—O3—C7	−59.2 (4)
C14—C9—C10—C11	0.0 (8)	C4—C3—O3—C7	60.2 (4)
C8—C9—C10—C11	−177.0 (5)	O3—C7—O5—C5	62.1 (4)
C9—C10—C11—C12	0.3 (10)	O1—C7—O5—C5	−61.6 (4)
C10—C11—C12—C13	−0.9 (11)	C4—C5—O5—C7	−60.8 (4)
C11—C12—C13—C14	1.3 (10)	C6—C5—O5—C7	60.0 (4)
C12—C13—C14—C9	−1.1 (9)	O8—C15—O6—C6	7.0 (6)
C10—C9—C14—C13	0.4 (8)	C16—C15—O6—C6	−172.6 (3)
C8—C9—C14—C13	177.3 (5)	C1—C6—O6—C15	153.8 (3)
O8—C15—C16—C17	−19.0 (7)	C5—C6—O6—C15	−85.3 (4)
O6—C15—C16—C17	160.6 (4)	O3'—C7'—O1'—C1'	63.1 (4)
O1'—C1'—C2'—O2'	−66.3 (4)	O5'—C7'—O1'—C1'	−62.2 (4)
C6'—C1'—C2'—O2'	176.0 (3)	C2'—C1'—O1'—C7'	−57.7 (4)
O1'—C1'—C2'—C3'	53.3 (4)	C6'—C1'—O1'—C7'	61.4 (4)
C6'—C1'—C2'—C3'	−64.4 (4)	O7'—C8'—O2'—C2'	−0.6 (6)
O2'—C2'—C3'—O3'	66.8 (4)	C9'—C8'—O2'—C2'	179.1 (3)
C1'—C2'—C3'—O3'	−52.6 (4)	C3'—C2'—O2'—C8'	121.2 (4)
O2'—C2'—C3'—C4'	−176.7 (3)	C1'—C2'—O2'—C8'	−119.5 (4)
C1'—C2'—C3'—C4'	63.9 (4)	O5'—C7'—O3'—C3'	61.3 (4)
O3'—C3'—C4'—O4'	−177.1 (3)	O1'—C7'—O3'—C3'	−63.6 (4)
C2'—C3'—C4'—O4'	64.8 (4)	C2'—C3'—O3'—C7'	58.1 (4)
O3'—C3'—C4'—C5'	60.1 (4)	C4'—C3'—O3'—C7'	−60.1 (4)
C2'—C3'—C4'—C5'	−58.0 (4)	O3'—C7'—O5'—C5'	−62.0 (4)
O4'—C4'—C5'—O5'	177.3 (3)	O1'—C7'—O5'—C5'	63.0 (4)
C3'—C4'—C5'—O5'	−59.7 (4)	C4'—C5'—O5'—C7'	60.3 (4)
O4'—C4'—C5'—C6'	−67.3 (4)	C6'—C5'—O5'—C7'	−61.1 (4)
C3'—C4'—C5'—C6'	55.7 (4)	O8'—C15'—O6'—C6'	−3.3 (6)
O1'—C1'—C6'—O6'	176.1 (3)	C16'—C15'—O6'—C6'	176.2 (3)
C2'—C1'—C6'—O6'	−64.3 (4)	C1'—C6'—O6'—C15'	−168.4 (3)
O1'—C1'—C6'—C5'	−61.3 (4)	C5'—C6'—O6'—C15'	73.5 (4)
C2'—C1'—C6'—C5'	58.4 (4)	C3—C4—O4—H18	−59 (3)
O5'—C5'—C6'—O6'	177.0 (3)	C3'—C4'—O4'—H18'	93 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4′—H18′···O4	0.84 (6)	2.09 (6)	2.858 (5)	151 (5)
O4—H18···O7′^i	0.82 (5)	1.98 (5)	2.785 (4)	165 (4)
C1—H1···O5^ii	1.00	2.43	3.364 (5)	155
C1′—H1′···O5′^ii	1.00	2.59	3.533 (5)	157
C3—H3···O7′^i	1.00	2.39	3.161 (5)	133
C3′—H3′···O7	1.00	2.58	3.482 (5)	150
C16—H16···O4′	0.95	2.55	3.308 (5)	136
C7—H7···O8′^iii	1.00	2.50	3.328 (5)	140
C6—H6···O5′^iii	1.00	2.39	3.208 (5)	138
C7′—H7′···O8^iv	1.00	2.43	3.202 (5)	133
C12′—H12′···O8′^v	0.95	2.60	3.540 (6)	171
C13—H13···O3′^vi	0.95	2.59	3.416 (6)	145

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