1,2:4,5-Di-O-iso­propyl­idene-β-D-erythro-hexo-2,3-diulo-2,6-pyran­ose

The crystal structure of title compound, C₁₂H₁₈O₆, has been determined using single-crystal data. There are two independent mol­ecules in the asymmetric unit. NMR coupling constants, dihedral angles as well as puckering parameters indicate the ³S₀ conformation of the pyran­ose ring in both mol­ecules A and B. The cis-fused 1,3-dioxolane ring in both mol­ecules A and B, adopts an E₄ conformation. The second five-membered 1,3-dioxolane ring, in mol­ecule A, has an E₂ conformation, whereas in mol­ecule B, this 1,3-dioxolane ring adopts an E₄ conformation. Molecules A form a zigzag infinite chain along the b axis with mol­ecules B as side chains. This explains why the displacement ellipsoids of atoms of mol­ecule B are substantially larger than those of mol­ecule A.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.091
• Data-to-parameter ratio = 12.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



STRVAL_01
         From the CIF: _refine_ls_abs_structure_Flack   -0.200
         From the CIF: _refine_ls_abs_structure_Flack_su    0.800
           Alert C Flack test results are meaningless.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.49
         From the CIF: _reflns_number_total               4781
         Count of symmetry unique reflns         2559
         Completeness (_total/calc)            186.83%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      2222
         Fraction of Friedel pairs measured     0.868
         Are heavy atom types Z>Si present           no
          ALERT: MoKa measured Friedel data cannot be used to
                 determine absolute structure in a light-atom
                 study EXCEPT under VERY special conditions.
                 It is preferred that Friedel data is merged in such cases.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

As a continuation of our research on the synthesis and structure determination of selected sugar amino derivatives (Koóš, Steiner, Langer et al., 2000; Koóš, Steiner, Gajdoš et al., 2000; Steiner et al., 1998), we have focused attention on 1,2:4,5-di-O-isopropylidene-β-D-erythro-hexo-2,3-diulo-2,6-pyranose, (I), as a potential starting material. This compound was prepared in two steps from D-fructose according to the procedure of Wang et al. (1997). The atom-numbering schemes of both molecules are presented in Fig. 1. The conformation of the pyranose ring of (I) is mentioned only twice in the literature. One proposal, based on the molecular model study, favored the ⁰S₃ conformation (McDonald, 1967), whereas a second possibility (more probable), based on the inspection of dihedral angles (from molecular model) and coupling constants (from NMR), was the ³S₀ conformation (Hervé du Penhoat & Perlin, 1979).

Correlation of dihedral angles associated with coupling constants J_5,6 = 2.2 Hz and J_5,6' = 0.9 Hz with corresponding dihedral angles (H5A—C5A—C6A-H6A1 and H5B—C5B—C6B-H6B1 about -70°, and H5A—C5A—C6A-H6A2 and H5B—C5B—C6B-H6B2 about 46°) obtained from X-ray crystallography as well as puckering parameters [Q = 0.476 (2) Å, ϕ = 193.5 (8)°, θ = 162.0 (2)° for molecule A, and Q = 0.511 (2) Å, ϕ = 218.2 (8)°, θ = 162.8 (2)° for molecule B] clearly indicate the ³S₀ conformation of the pyranose ring (O6—C2—C3—C4—C5—C6) in both molecules A and B (Fig 1). The cis-fused 1,3-dioxolane ring (C4—O4—C10—O5—C5 in both molecules A and B) adopts the E₄ conformation, where the C4, O4, C10 and O5 atoms lie almost in a plane [for molecule A, dihedral angle C4—O4—C10—O5 = -3.2 (2)°, and puckering parameters Q = 0.347 (2) Å and ϕ = 247.7 (4)°; for molecule B, dihedral angle C4—O4—C10—O5 = -2.9 (2)°, and puckering parameters Q = 0.367 (2) Å and ϕ = 248.4 (3)°] and C5 is directed below this plane. The second five-membered 1,3-dioxolane ring (O1—C1—C2—O2—C7 in the molecule A) has an E₂ conformation, where the O1, C1, C2, and O2 atoms lie almost in a plane [dihedral angle O1—C1—C2—O2 is 3.4 (2)°, and puckering parameters Q = 0.291 (2) Å and ϕ = 330.1 (4)°] and C7 faces below this plane. However, in molecule B, this 1,3-dioxolane ring adopts the E₄ conformation, where the O2, C7, O1, and C1 atoms lie in a plane [dihedral angle O2—C7—O1—C1 is 0.8 (3)°, and puckering parameters Q = 0.171 (2) Å and ϕ = 255.7 (9)°] with C2 directed below this plane. It is also noteworthy, that both molecules in the asymetric unit have the same absolute configuration: S on C2, R on C4 and C5.

There were also C6A–H6A1···O2B and C8A–H8A2···O1A hydrogen bonds (Table 2) which stabilize the crystal structure of the title compound. Molecules A and B are connected through hydrogen bonds in such a way that molecules A form infinite zigzag chain along the b axis with side chains consisting of molecules B (Fig. 2). This could be also explanation of slightly larger thermal motion of atoms of molecule B in comparison with those of molecule A.

S2. Experimental

Compound (I) was prepared in two steps from D-fructose according to the procedure of Wang et al. (1997).

S3. Refinement

Data were collected using a Siemens SMART CCD diffractometer at room temperature. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal-to-detector distance of 3.97 cm and 30 s per frame. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 6826 reflections with I>10σ(I) after integration of all the frames data using SAINT (Siemens, 1995). The data were empirically corrected for absorption and other effects using SADABS (Sheldrick, 1996) based on the method of Blessing (1995). H atoms were constrained to the ideal geometry using an appropriate riding model. For methyl groups, the C—H distances (0.93 Å) and C—C—H angles (109.5°) were kept fixed, while the torsion angles were allowed to refine with the starting position based on the threefold averaged circular Fourier synthesis.

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and XPREP (Siemens, 1995); program(s) used to solve structure: XFPA98 (Pavelčík, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: PLATON (Spek, 2001).

Figures

	Fig. 1. The atom-numbering scheme and displacement ellipsoids at the 30% probability level for molecules A and B of (I).
	Fig. 2. Hydrogen-bond scheme projected along the c axis. Molecules A form a zigzag infinite chain along the b axis with molecules B as side chains.

1,2:4,5-di-O-isopropylidene-β-D-erythro-hexo-2,3-diulo-2,6 -pyranose

Crystal data

C12H18O6	F(000) = 552
Mr = 258.27	Dx = 1.322 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.9909 (2) Å	Cell parameters from 6790 reflections
b = 10.5488 (2) Å	θ = 1.8–25.5°
c = 11.3876 (2) Å	µ = 0.11 mm^−1
β = 100.526 (1)°	T = 297 K
V = 1298.07 (4) Å^3	Needle, colorless
Z = 4	0.55 × 0.16 × 0.15 mm

Data collection

Siemens SMART CCD diffractometer	4781 independent reflections
Radiation source: fine-focus sealed tube	3804 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scans 0.30° frames, 30 s each	θmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (Blessing, 1995)	h = −13→13
Tmin = 0.944, Tmax = 0.984	k = −12→12
13132 measured reflections	l = −13→13

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0502P)^2 + 0.0759P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.091	(Δ/σ)max = 0.009
S = 1.02	Δρmax = 0.15 e Å^−3
4781 reflections	Δρmin = −0.12 e Å^−3
370 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0159 (17)
Primary atom site location: structure-invariant direct methods	Absolute structure: (Flack, 1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.2 (8)

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
O1A	0.46357 (13)	−0.35918 (16)	0.92957 (16)	0.0640 (5)
O2A	0.31122 (12)	−0.25867 (15)	0.99815 (12)	0.0490 (3)
O3A	0.18110 (15)	−0.52697 (17)	0.96094 (18)	0.0780 (5)
O4A	−0.04943 (13)	−0.43655 (16)	0.97465 (15)	0.0633 (5)
O5A	−0.07792 (13)	−0.31714 (15)	0.80614 (13)	0.0569 (4)
O6A	0.18493 (12)	−0.25455 (14)	0.80892 (11)	0.0457 (3)
C1A	0.35509 (18)	−0.3934 (2)	0.8511 (2)	0.0527 (5)
H1A1	0.3445	−0.4847	0.8493	0.079 (8)*
H1A2	0.3572	−0.3638	0.7709	0.073 (8)*
C2A	0.25187 (16)	−0.32976 (19)	0.90008 (17)	0.0409 (4)
C3A	0.16267 (18)	−0.4155 (2)	0.94876 (18)	0.0465 (5)
C4A	0.05006 (18)	−0.3531 (2)	0.98146 (18)	0.0481 (5)
H4A	0.0711	−0.3191	1.0627	0.058 (6)*
C5A	−0.00039 (18)	−0.2480 (2)	0.89689 (18)	0.0495 (5)
H5A	−0.0502	−0.1899	0.9359	0.061 (6)*
C6A	0.09507 (19)	−0.1751 (2)	0.8465 (2)	0.0525 (5)
H6A1	0.0543	−0.1254	0.7790	0.066 (7)*
H6A2	0.1364	−0.1167	0.9067	0.058 (7)*
C7A	0.43973 (18)	−0.2468 (2)	0.9890 (2)	0.0535 (5)
C8A	0.4591 (3)	−0.1314 (3)	0.9176 (3)	0.0748 (8)
H8A1	0.5441	−0.1271	0.9085	0.093 (9)*
H8A2	0.4384	−0.0569	0.9583	0.092 (9)*
H8A3	0.4070	−0.1364	0.8402	0.084 (9)*
C9A	0.5153 (2)	−0.2488 (4)	1.1115 (2)	0.0846 (9)
H9A1	0.4956	−0.3233	1.1527	0.087 (10)*
H9A2	0.4973	−0.1747	1.1543	0.105 (12)*
H9A3	0.6015	−0.2496	1.1067	0.088 (9)*
C10A	−0.1300 (2)	−0.4180 (3)	0.8613 (2)	0.0638 (7)
C11A	−0.1310 (4)	−0.5329 (4)	0.7862 (4)	0.1112 (12)
H11A	−0.1834	−0.5188	0.7102	0.154 (17)*
H11B	−0.1620	−0.6035	0.8252	0.165 (18)*
H11C	−0.0484	−0.5510	0.7747	0.112 (12)*
C12A	−0.2548 (2)	−0.3830 (5)	0.8859 (4)	0.1153 (15)
H12A	−0.2490	−0.3049	0.9299	0.17 (2)*
H12B	−0.2840	−0.4489	0.9320	0.097 (10)*
H12C	−0.3116	−0.3729	0.8118	0.110 (11)*
O1B	1.03904 (19)	0.2009 (3)	0.5286 (2)	0.1213 (10)
O2B	0.98429 (12)	0.02978 (15)	0.62390 (13)	0.0550 (4)
O3B	0.77800 (17)	−0.0363 (2)	0.38418 (14)	0.0741 (5)
O4B	0.65393 (14)	−0.19692 (16)	0.51145 (16)	0.0633 (4)
O5B	0.58048 (12)	−0.03305 (16)	0.60652 (13)	0.0559 (4)
O6B	0.79973 (15)	0.13743 (16)	0.62463 (17)	0.0691 (5)
C1B	0.9217 (3)	0.1760 (3)	0.4760 (3)	0.0867 (10)
H1B1	0.9186	0.1431	0.3960	0.154 (18)*
H1B2	0.8714	0.2520	0.4714	0.159 (17)*
C2B	0.8765 (2)	0.0775 (2)	0.5551 (2)	0.0544 (6)
C3B	0.80168 (18)	−0.0306 (2)	0.49145 (19)	0.0495 (5)
C4B	0.75480 (18)	−0.1258 (2)	0.57086 (19)	0.0498 (5)
H4B	0.8221	−0.1826	0.6064	0.053 (6)*
C5B	0.70194 (19)	−0.0604 (2)	0.66769 (19)	0.0532 (5)
H5B	0.6986	−0.1195	0.7334	0.054 (6)*
C6B	0.7682 (2)	0.0589 (3)	0.7151 (2)	0.0699 (7)
H6B1	0.7158	0.1064	0.7594	0.086 (9)*
H6B2	0.8431	0.0363	0.7703	0.079 (8)*
C7B	1.08397 (19)	0.1177 (2)	0.6197 (2)	0.0570 (6)
C8B	1.1137 (4)	0.1885 (3)	0.7333 (3)	0.0951 (10)
H8B1	1.1788	0.2481	0.7290	0.104 (10)*
H8B2	1.1402	0.1303	0.7977	0.127 (13)*
H8B3	1.0415	0.2331	0.7471	0.18 (2)*
C9B	1.1907 (3)	0.0434 (4)	0.5934 (5)	0.1187 (14)
H9B1	1.1666	−0.0011	0.5193	0.16 (2)*
H9B2	1.2167	−0.0164	0.6565	0.23 (3)*
H9B3	1.2579	0.0998	0.5874	0.110 (11)*
C10B	0.54155 (19)	−0.1368 (2)	0.5300 (2)	0.0543 (5)
C11B	0.4696 (3)	−0.0876 (3)	0.4157 (2)	0.0775 (8)
H11D	0.4008	−0.0386	0.4317	0.126 (13)*
H11E	0.4395	−0.1575	0.3645	0.103 (11)*
H11F	0.5219	−0.0352	0.3772	0.084 (9)*
C12B	0.4701 (3)	−0.2314 (3)	0.5881 (3)	0.0782 (8)
H12D	0.5196	−0.2593	0.6619	0.098 (10)*
H12E	0.4494	−0.3027	0.5360	0.115 (12)*
H12F	0.3956	−0.1928	0.6037	0.117 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0412 (8)	0.0605 (10)	0.0885 (12)	0.0045 (7)	0.0067 (7)	−0.0160 (9)
O2A	0.0428 (7)	0.0569 (9)	0.0474 (7)	−0.0034 (7)	0.0079 (6)	−0.0096 (7)
O3A	0.0645 (10)	0.0472 (11)	0.1264 (16)	0.0071 (8)	0.0285 (10)	0.0280 (11)
O4A	0.0452 (8)	0.0711 (11)	0.0742 (10)	−0.0028 (8)	0.0128 (7)	0.0279 (9)
O5A	0.0457 (8)	0.0652 (10)	0.0565 (9)	−0.0002 (7)	0.0005 (7)	0.0156 (8)
O6A	0.0480 (7)	0.0443 (8)	0.0450 (7)	0.0017 (6)	0.0088 (6)	0.0058 (7)
C1A	0.0454 (11)	0.0485 (14)	0.0648 (15)	−0.0005 (9)	0.0119 (10)	−0.0082 (11)
C2A	0.0395 (10)	0.0407 (11)	0.0419 (10)	0.0003 (8)	0.0058 (8)	−0.0018 (9)
C3A	0.0448 (11)	0.0436 (13)	0.0480 (12)	0.0010 (9)	0.0002 (9)	0.0102 (10)
C4A	0.0462 (11)	0.0565 (13)	0.0420 (11)	0.0000 (10)	0.0097 (8)	0.0075 (10)
C5A	0.0472 (11)	0.0497 (12)	0.0525 (12)	0.0112 (10)	0.0116 (9)	0.0051 (11)
C6A	0.0535 (12)	0.0399 (12)	0.0636 (14)	0.0063 (10)	0.0092 (11)	0.0074 (11)
C7A	0.0409 (10)	0.0583 (14)	0.0610 (12)	−0.0038 (10)	0.0087 (9)	−0.0123 (12)
C8A	0.0777 (18)	0.0625 (17)	0.089 (2)	−0.0188 (15)	0.0275 (16)	−0.0138 (16)
C9A	0.0571 (16)	0.113 (3)	0.0765 (17)	−0.0100 (18)	−0.0065 (12)	−0.014 (2)
C10A	0.0412 (11)	0.0673 (17)	0.0798 (16)	−0.0016 (11)	0.0028 (11)	0.0216 (14)
C11A	0.107 (3)	0.082 (2)	0.130 (3)	−0.016 (2)	−0.016 (2)	−0.006 (2)
C12A	0.0431 (15)	0.150 (4)	0.155 (3)	0.0150 (18)	0.0248 (18)	0.071 (3)
O1B	0.0909 (15)	0.140 (2)	0.1132 (16)	−0.0579 (14)	−0.0336 (12)	0.0867 (16)
O2B	0.0464 (8)	0.0558 (9)	0.0592 (9)	−0.0068 (7)	−0.0003 (6)	0.0209 (8)
O3B	0.0818 (11)	0.0904 (13)	0.0476 (10)	0.0012 (10)	0.0052 (8)	0.0011 (9)
O4B	0.0526 (9)	0.0520 (9)	0.0847 (11)	−0.0031 (7)	0.0109 (8)	−0.0208 (8)
O5B	0.0463 (8)	0.0555 (9)	0.0646 (9)	0.0041 (7)	0.0069 (6)	−0.0119 (8)
O6B	0.0627 (10)	0.0480 (9)	0.0935 (13)	−0.0004 (8)	0.0060 (9)	−0.0108 (9)
C1B	0.0776 (18)	0.080 (2)	0.093 (2)	−0.0131 (16)	−0.0088 (15)	0.0458 (18)
C2B	0.0512 (12)	0.0502 (13)	0.0574 (13)	0.0008 (10)	−0.0018 (10)	0.0122 (11)
C3B	0.0465 (11)	0.0524 (12)	0.0476 (12)	0.0077 (10)	0.0029 (9)	0.0004 (11)
C4B	0.0442 (11)	0.0459 (12)	0.0572 (13)	0.0045 (10)	0.0037 (9)	−0.0003 (10)
C5B	0.0508 (12)	0.0600 (14)	0.0483 (12)	0.0000 (10)	0.0075 (9)	−0.0015 (11)
C6B	0.0583 (15)	0.088 (2)	0.0625 (15)	−0.0054 (14)	0.0078 (12)	−0.0278 (15)
C7B	0.0514 (12)	0.0594 (14)	0.0584 (13)	−0.0103 (11)	0.0052 (10)	0.0188 (11)
C8B	0.116 (3)	0.081 (2)	0.084 (2)	−0.037 (2)	0.0050 (18)	0.0006 (18)
C9B	0.088 (2)	0.106 (3)	0.182 (4)	−0.016 (2)	0.078 (3)	−0.004 (3)
C10B	0.0457 (11)	0.0549 (14)	0.0618 (13)	−0.0018 (10)	0.0082 (10)	−0.0101 (11)
C11B	0.0696 (17)	0.092 (2)	0.0650 (16)	−0.0001 (16)	−0.0037 (13)	−0.0001 (15)
C12B	0.0671 (16)	0.077 (2)	0.091 (2)	−0.0153 (15)	0.0139 (14)	0.0022 (17)

Geometric parameters (Å, º)

O1A—C1A	1.400 (3)	O1B—C1B	1.345 (3)
O1A—C7A	1.413 (3)	O1B—C7B	1.379 (3)
O2A—C2A	1.403 (2)	O2B—C2B	1.389 (2)
O2A—C7A	1.441 (2)	O2B—C7B	1.443 (3)
O3A—C3A	1.197 (3)	O3B—C3B	1.203 (3)
O4A—C4A	1.395 (3)	O4B—C4B	1.406 (3)
O4A—C10A	1.439 (3)	O4B—C10B	1.438 (3)
O5A—C10A	1.409 (3)	O5B—C10B	1.415 (3)
O5A—C5A	1.416 (3)	O5B—C5B	1.418 (2)
O6A—C2A	1.403 (2)	O6B—C2B	1.408 (3)
O6A—C6A	1.420 (2)	O6B—C6B	1.414 (3)
C1A—C2A	1.510 (3)	C1B—C2B	1.517 (3)
C1A—H1A1	0.9700	C1B—H1B1	0.9700
C1A—H1A2	0.9700	C1B—H1B2	0.9700
C2A—C3A	1.512 (3)	C2B—C3B	1.511 (3)
C3A—C4A	1.507 (3)	C3B—C4B	1.504 (3)
C4A—C5A	1.507 (3)	C4B—C5B	1.504 (3)
C4A—H4A	0.9800	C4B—H4B	0.9800
C5A—C6A	1.497 (3)	C5B—C6B	1.504 (4)
C5A—H5A	0.9800	C5B—H5B	0.9800
C6A—H6A1	0.9700	C6B—H6B1	0.9700
C6A—H6A2	0.9700	C6B—H6B2	0.9700
C7A—C9A	1.488 (3)	C7B—C8B	1.478 (4)
C7A—C8A	1.500 (4)	C7B—C9B	1.486 (4)
C8A—H8A1	0.9600	C8B—H8B1	0.9600
C8A—H8A2	0.9600	C8B—H8B2	0.9600
C8A—H8A3	0.9600	C8B—H8B3	0.9600
C9A—H9A1	0.9600	C9B—H9B1	0.9600
C9A—H9A2	0.9600	C9B—H9B2	0.9600
C9A—H9A3	0.9600	C9B—H9B3	0.9600
C10A—C11A	1.482 (5)	C10B—C11B	1.487 (3)
C10A—C12A	1.496 (4)	C10B—C12B	1.496 (3)
C11A—H11A	0.9600	C11B—H11D	0.9600
C11A—H11B	0.9600	C11B—H11E	0.9600
C11A—H11C	0.9600	C11B—H11F	0.9600
C12A—H12A	0.9600	C12B—H12D	0.9600
C12A—H12B	0.9600	C12B—H12E	0.9600
C12A—H12C	0.9600	C12B—H12F	0.9600
C1A—O1A—C7A	108.11 (15)	C1B—O1B—C7B	113.15 (19)
C2A—O2A—C7A	107.94 (14)	C2B—O2B—C7B	108.82 (16)
C4A—O4A—C10A	108.15 (16)	C4B—O4B—C10B	108.47 (16)
C10A—O5A—C5A	107.65 (17)	C10B—O5B—C5B	107.25 (16)
C2A—O6A—C6A	114.21 (14)	C2B—O6B—C6B	113.49 (18)
O1A—C1A—C2A	105.05 (17)	O1B—C1B—C2B	105.1 (2)
O1A—C1A—H1A1	110.7	O1B—C1B—H1B1	110.7
C2A—C1A—H1A1	110.7	C2B—C1B—H1B1	110.7
O1A—C1A—H1A2	110.7	O1B—C1B—H1B2	110.7
C2A—C1A—H1A2	110.7	C2B—C1B—H1B2	110.7
H1A1—C1A—H1A2	108.8	H1B1—C1B—H1B2	108.8
O6A—C2A—O2A	113.04 (15)	O2B—C2B—O6B	112.50 (18)
O6A—C2A—C1A	107.80 (17)	O2B—C2B—C3B	109.31 (18)
O2A—C2A—C1A	105.07 (15)	O6B—C2B—C3B	106.19 (17)
O6A—C2A—C3A	108.79 (15)	O2B—C2B—C1B	104.19 (18)
O2A—C2A—C3A	105.44 (16)	O6B—C2B—C1B	108.7 (2)
C1A—C2A—C3A	116.81 (18)	C3B—C2B—C1B	116.1 (2)
O3A—C3A—C4A	122.0 (2)	O3B—C3B—C4B	122.9 (2)
O3A—C3A—C2A	121.5 (2)	O3B—C3B—C2B	121.5 (2)
C4A—C3A—C2A	116.49 (18)	C4B—C3B—C2B	115.55 (17)
O4A—C4A—C3A	112.42 (19)	O4B—C4B—C3B	113.19 (17)
O4A—C4A—C5A	103.64 (15)	O4B—C4B—C5B	102.78 (16)
C3A—C4A—C5A	112.73 (17)	C3B—C4B—C5B	110.81 (19)
O4A—C4A—H4A	109.3	O4B—C4B—H4B	109.9
C3A—C4A—H4A	109.3	C3B—C4B—H4B	109.9
C5A—C4A—H4A	109.3	C5B—C4B—H4B	109.9
O5A—C5A—C6A	110.84 (17)	O5B—C5B—C6B	110.9 (2)
O5A—C5A—C4A	100.91 (17)	O5B—C5B—C4B	100.85 (16)
C6A—C5A—C4A	114.90 (17)	C6B—C5B—C4B	114.85 (19)
O5A—C5A—H5A	109.9	O5B—C5B—H5B	110.0
C6A—C5A—H5A	109.9	C6B—C5B—H5B	110.0
C4A—C5A—H5A	109.9	C4B—C5B—H5B	110.0
O6A—C6A—C5A	112.79 (18)	O6B—C6B—C5B	113.31 (19)
O6A—C6A—H6A1	109.0	O6B—C6B—H6B1	108.9
C5A—C6A—H6A1	109.0	C5B—C6B—H6B1	108.9
O6A—C6A—H6A2	109.0	O6B—C6B—H6B2	108.9
C5A—C6A—H6A2	109.0	C5B—C6B—H6B2	108.9
H6A1—C6A—H6A2	107.8	H6B1—C6B—H6B2	107.7
O1A—C7A—O2A	103.40 (16)	O1B—C7B—O2B	105.32 (16)
O1A—C7A—C9A	108.5 (2)	O1B—C7B—C8B	109.2 (3)
O2A—C7A—C9A	108.48 (19)	O2B—C7B—C8B	110.1 (2)
O1A—C7A—C8A	111.37 (18)	O1B—C7B—C9B	111.8 (3)
O2A—C7A—C8A	110.3 (2)	O2B—C7B—C9B	107.5 (2)
C9A—C7A—C8A	114.2 (2)	C8B—C7B—C9B	112.7 (3)
C7A—C8A—H8A1	109.5	C7B—C8B—H8B1	109.5
C7A—C8A—H8A2	109.5	C7B—C8B—H8B2	109.5
H8A1—C8A—H8A2	109.5	H8B1—C8B—H8B2	109.5
C7A—C8A—H8A3	109.5	C7B—C8B—H8B3	109.5
H8A1—C8A—H8A3	109.5	H8B1—C8B—H8B3	109.5
H8A2—C8A—H8A3	109.5	H8B2—C8B—H8B3	109.5
C7A—C9A—H9A1	109.5	C7B—C9B—H9B1	109.5
C7A—C9A—H9A2	109.5	C7B—C9B—H9B2	109.5
H9A1—C9A—H9A2	109.5	H9B1—C9B—H9B2	109.5
C7A—C9A—H9A3	109.5	C7B—C9B—H9B3	109.5
H9A1—C9A—H9A3	109.5	H9B1—C9B—H9B3	109.5
H9A2—C9A—H9A3	109.5	H9B2—C9B—H9B3	109.5
O5A—C10A—O4A	105.60 (17)	O5B—C10B—O4B	105.09 (15)
O5A—C10A—C11A	108.8 (3)	O5B—C10B—C11B	108.8 (2)
O4A—C10A—C11A	110.2 (2)	O4B—C10B—C11B	111.0 (2)
O5A—C10A—C12A	111.0 (2)	O5B—C10B—C12B	111.5 (2)
O4A—C10A—C12A	107.5 (3)	O4B—C10B—C12B	107.7 (2)
C11A—C10A—C12A	113.5 (3)	C11B—C10B—C12B	112.4 (2)
C10A—C11A—H11A	109.5	C10B—C11B—H11D	109.5
C10A—C11A—H11B	109.5	C10B—C11B—H11E	109.5
H11A—C11A—H11B	109.5	H11D—C11B—H11E	109.5
C10A—C11A—H11C	109.5	C10B—C11B—H11F	109.5
H11A—C11A—H11C	109.5	H11D—C11B—H11F	109.5
H11B—C11A—H11C	109.5	H11E—C11B—H11F	109.5
C10A—C12A—H12A	109.5	C10B—C12B—H12D	109.5
C10A—C12A—H12B	109.5	C10B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C10A—C12A—H12C	109.5	C10B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
C4A—O4A—C10A—O5A	−3.2 (2)	O2B—C7B—O1B—C1B	0.8 (3)
C4B—O4B—C10B—O5B	−2.9 (2)	H5A—C5A—C6A—H6A1	−70
O1A—C1A—C2A—O2A	3.4 (2)	H5B—C5B—C6B—H6B1	−71
O1B—C1B—C2B—O2B	−17.3 (3)	H5A—C5A—C6A—H6A2	48
O2A—C7A—O1A—C1A	32.5 (2)	H5B—C5B—C6B—H6B2	46

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6A—H6A1···O2B^i	0.97	2.42	3.382 (3)	169
C8A—H8A2···O1A^ii	0.96	2.57	3.384 (4)	142

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