2,6-Anhydro-1,3-di-O-benzyl-d-mannitol.

In the title compound, C(20)H(24)O(5), the six-membered pyran-ose ring adopts a chair conformation. The dihedral angle between the planes of the phenyl groups of the benzyl substituents is 63.1°. Two types of inter-molecular O-H⋯O hydrogen bonds lead to the formation of infinite chains along the b axis. Only weak C-H⋯O contacts exist between neighboring chains.

Related literature

For syntheses of this and similar compounds, see: Barker (1970 ▶); Doboszewski (1997 ▶, 2009 ▶); Doboszewski & de Siqueria (2010 ▶); Hartman (1970a ▶,b ▶). For related structures, see: Boeyens et al. (1983 ▶); Doboszewski & Nazarenko (2003 ▶); Guiry et al. (2008 ▶); Hong et al. (2005 ▶); Vidra et al. (1982 ▶). For conformations of six-membered rings, see: Schwarz (1973 ▶); Cremer & Pople (1975 ▶); Boeyens & Dobson (1987 ▶). For hydrogen bonding in carbohydrate chemistry, see Gilli & Gilli (2009 ▶); Desiraju & Steiner (1999 ▶); Jeffrey (1997 ▶), and references therein.

Experimental

Crystal data

C20H24O5

M = 344.39

Monoclinic,

a = 5.6584 (10) Å

b = 7.9610 (12) Å

c = 19.808 (4) Å

β = 91.968 (6)°

V = 891.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.6 × 0.4 × 0.05 mm

Data collection

Bruker SMART X2S diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008b ▶) T min = 0.91, T max = 0.98

8624 measured reflections

1695 independent reflections

1458 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.082

S = 0.99

1695 reflections

228 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.14 e Å−3

Data collection: GIS (Bruker, 2010 ▶); cell refinement: APEX2 (Bruker, 2010 ▶) and SAINT (Bruker, 2009 ▶); data reduction: SAINT and XPREP in SHELXTL (Sheldrick, 2008a ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008a ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811022306/zl2379sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022306/zl2379Isup2.hkl

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

Enhanced figure: interactive version of Fig. 5

C20H24O5	F(000) = 368
Mr = 344.39	Dx = 1.283 Mg m−3
Monoclinic, P21	Melting point: 454(3) K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 5.6584 (10) Å	Cell parameters from 2505 reflections
b = 7.9610 (12) Å	θ = 2.1–25.0°
c = 19.808 (4) Å	µ = 0.09 mm−1
β = 91.968 (6)°	T = 200 K
V = 891.8 (3) Å3	Plate, colourless
Z = 2	0.6 × 0.4 × 0.05 mm

Bruker SMART X2S diffractometer	1695 independent reflections
Radiation source: XOS X-beam microfocus source	1458 reflections with I > 2σ(I)
doubly curved silicon crystal	Rint = 0.052
ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b)	h = −6→6
Tmin = 0.91, Tmax = 0.98	k = −9→9
8624 measured reflections	l = −23→23

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0509P)2] where P = (Fo2 + 2Fc2)/3
1695 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.14 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.5054 (4)	0.6502 (3)	0.64947 (9)	0.0699 (7)
O2	0.6876 (3)	0.44181 (18)	0.54580 (7)	0.0288 (4)
O3	0.8458 (3)	0.2160 (2)	0.70085 (7)	0.0329 (4)
O4	1.0068 (3)	−0.0091 (2)	0.59915 (8)	0.0389 (4)
H4	0.9884	−0.0925	0.5735	0.047*
O5	1.0291 (3)	0.2171 (2)	0.48840 (8)	0.0311 (4)
H5	1.1187	0.1341	0.4836	0.037*
C1	0.7134 (5)	0.5512 (3)	0.65761 (12)	0.0426 (7)
H1A	0.7402	0.5208	0.7057	0.051*
H1B	0.8523	0.6151	0.6427	0.051*
C2	0.6801 (4)	0.3952 (3)	0.61547 (11)	0.0296 (5)
H2A	0.5206	0.3471	0.6240	0.036*
C3	0.8671 (4)	0.2607 (3)	0.63147 (10)	0.0272 (5)
H3A	1.0284	0.3072	0.6241	0.033*
C4	0.8223 (4)	0.1094 (3)	0.58552 (10)	0.0285 (5)
H4A	0.6689	0.0569	0.5976	0.034*
C5	0.8049 (4)	0.1607 (3)	0.51169 (11)	0.0275 (5)
H5A	0.7506	0.0621	0.4839	0.033*
C6	0.6287 (4)	0.3020 (3)	0.50228 (11)	0.0311 (5)
H6A	0.6261	0.3397	0.4546	0.037*
H6B	0.4687	0.2606	0.5123	0.037*
C9	1.0627 (4)	0.1952 (4)	0.73746 (12)	0.0466 (7)
H9A	1.1698	0.2896	0.7274	0.056*
H9B	1.1392	0.0897	0.7233	0.056*
C10	0.5053 (8)	0.7934 (4)	0.69327 (14)	0.0781 (12)
H10A	0.3683	0.8656	0.6807	0.094*
H10B	0.6509	0.8596	0.6867	0.094*
C11	1.0226 (4)	0.1894 (3)	0.81204 (11)	0.0358 (6)
C12	0.8296 (5)	0.2669 (4)	0.84079 (12)	0.0436 (7)
H12A	0.7150	0.3227	0.8127	0.052*
C13	0.8036 (5)	0.2634 (4)	0.90972 (13)	0.0538 (8)
H13A	0.6711	0.3162	0.9289	0.065*
C14	0.9691 (5)	0.1834 (5)	0.95082 (13)	0.0595 (9)
H14A	0.9516	0.1822	0.9983	0.071*
C15	1.1608 (5)	0.1049 (4)	0.92311 (13)	0.0579 (8)
H15A	1.2745	0.0488	0.9514	0.069*
C16	1.1858 (5)	0.1086 (4)	0.85404 (13)	0.0464 (7)
H16A	1.3177	0.0545	0.8351	0.056*
C21	0.4931 (5)	0.7468 (4)	0.76631 (13)	0.0437 (7)
C22	0.3085 (5)	0.6518 (4)	0.79079 (15)	0.0546 (8)
H22A	0.1873	0.6120	0.7605	0.066*
C23	0.2996 (6)	0.6149 (5)	0.85879 (17)	0.0656 (9)
H23A	0.1729	0.5496	0.8750	0.079*
C24	0.4711 (7)	0.6713 (5)	0.90252 (15)	0.0693 (10)
H24A	0.4632	0.6463	0.9493	0.083*
C25	0.6537 (6)	0.7633 (5)	0.87996 (16)	0.0699 (10)
H25A	0.7729	0.8032	0.9109	0.084*
C26	0.6663 (5)	0.7989 (4)	0.81241 (16)	0.0553 (8)
H26A	0.7974	0.8609	0.7970	0.066*

	U11	U22	U33	U12	U13	U23
O1	0.1104 (18)	0.0642 (16)	0.0345 (10)	0.0575 (15)	−0.0080 (10)	−0.0070 (10)
O2	0.0307 (9)	0.0287 (10)	0.0270 (8)	0.0029 (7)	0.0009 (6)	−0.0007 (7)
O3	0.0340 (8)	0.0391 (10)	0.0257 (7)	0.0029 (8)	0.0014 (6)	0.0036 (7)
O4	0.0506 (11)	0.0277 (10)	0.0382 (9)	0.0118 (9)	−0.0026 (7)	−0.0040 (7)
O5	0.0257 (8)	0.0284 (10)	0.0397 (9)	0.0018 (7)	0.0072 (6)	0.0026 (7)
C1	0.0646 (18)	0.0344 (16)	0.0288 (13)	0.0156 (14)	0.0024 (11)	−0.0013 (11)
C2	0.0313 (13)	0.0317 (14)	0.0262 (11)	0.0024 (11)	0.0055 (9)	0.0001 (10)
C3	0.0256 (11)	0.0299 (14)	0.0263 (11)	−0.0014 (10)	0.0041 (8)	−0.0009 (10)
C4	0.0264 (12)	0.0259 (13)	0.0333 (12)	−0.0015 (11)	0.0022 (9)	−0.0001 (10)
C5	0.0225 (11)	0.0265 (13)	0.0336 (12)	−0.0063 (10)	0.0030 (9)	−0.0040 (10)
C6	0.0273 (12)	0.0346 (14)	0.0312 (12)	−0.0036 (11)	−0.0020 (9)	−0.0030 (11)
C9	0.0378 (13)	0.066 (2)	0.0357 (13)	0.0138 (15)	0.0003 (10)	−0.0026 (13)
C10	0.144 (3)	0.050 (2)	0.0422 (16)	0.048 (2)	0.0237 (18)	0.0006 (14)
C11	0.0359 (13)	0.0372 (16)	0.0341 (12)	0.0030 (12)	−0.0020 (10)	−0.0041 (11)
C12	0.0444 (15)	0.0501 (18)	0.0364 (13)	0.0080 (14)	0.0019 (10)	−0.0003 (12)
C13	0.0500 (17)	0.067 (2)	0.0445 (15)	0.0013 (16)	0.0104 (12)	−0.0051 (15)
C14	0.0630 (18)	0.087 (3)	0.0279 (13)	−0.006 (2)	−0.0005 (12)	0.0018 (15)
C15	0.0548 (18)	0.077 (2)	0.0411 (16)	0.0043 (18)	−0.0142 (13)	0.0063 (16)
C16	0.0409 (15)	0.0557 (18)	0.0421 (15)	0.0055 (14)	−0.0052 (11)	−0.0024 (13)
C21	0.0590 (17)	0.0325 (16)	0.0403 (13)	0.0145 (14)	0.0118 (12)	−0.0024 (12)
C22	0.0435 (16)	0.057 (2)	0.0626 (19)	0.0016 (16)	−0.0069 (13)	−0.0192 (16)
C23	0.062 (2)	0.064 (2)	0.073 (2)	−0.0005 (18)	0.0332 (17)	0.0043 (19)
C24	0.078 (2)	0.088 (3)	0.0422 (16)	0.030 (2)	0.0101 (16)	0.0052 (17)
C25	0.0581 (19)	0.088 (3)	0.062 (2)	0.0231 (19)	−0.0177 (15)	−0.025 (2)
C26	0.0460 (17)	0.0468 (18)	0.074 (2)	−0.0019 (15)	0.0154 (14)	−0.0077 (16)

O1—C1	1.421 (3)	C10—C21	1.498 (4)
O1—C10	1.433 (4)	C10—H10A	0.9900
O2—C2	1.431 (3)	C10—H10B	0.9900
O2—C6	1.440 (3)	C11—C16	1.381 (3)
O3—C9	1.413 (3)	C11—C12	1.393 (3)
O3—C3	1.429 (2)	C12—C13	1.379 (3)
O4—C4	1.426 (3)	C12—H12A	0.9500
O4—H4	0.8400	C13—C14	1.376 (4)
O5—C5	1.437 (2)	C13—H13A	0.9500
O5—H5	0.8400	C14—C15	1.382 (4)
C1—C2	1.505 (3)	C14—H14A	0.9500
C1—H1A	0.9900	C15—C16	1.381 (3)
C1—H1B	0.9900	C15—H15A	0.9500
C2—C3	1.531 (3)	C16—H16A	0.9500
C2—H2A	1.0000	C21—C26	1.381 (4)
C3—C4	1.526 (3)	C21—C22	1.390 (4)
C3—H3A	1.0000	C22—C23	1.381 (4)
C4—C5	1.518 (3)	C22—H22A	0.9500
C4—H4A	1.0000	C23—C24	1.355 (5)
C5—C6	1.511 (3)	C23—H23A	0.9500
C5—H5A	1.0000	C24—C25	1.355 (5)
C6—H6A	0.9900	C24—H24A	0.9500
C6—H6B	0.9900	C25—C26	1.372 (4)
C9—C11	1.503 (3)	C25—H25A	0.9500
C9—H9A	0.9900	C26—H26A	0.9500
C9—H9B	0.9900
C1—O1—C10	113.0 (2)	C11—C9—H9B	109.6
C2—O2—C6	111.27 (16)	H9A—C9—H9B	108.1
C9—O3—C3	114.99 (16)	O1—C10—C21	112.9 (3)
C4—O4—H4	109.5	O1—C10—H10A	109.0
C5—O5—H5	109.5	C21—C10—H10A	109.0
O1—C1—C2	107.9 (2)	O1—C10—H10B	109.0
O1—C1—H1A	110.1	C21—C10—H10B	109.0
C2—C1—H1A	110.1	H10A—C10—H10B	107.8
O1—C1—H1B	110.1	C16—C11—C12	118.5 (2)
C2—C1—H1B	110.1	C16—C11—C9	119.1 (2)
H1A—C1—H1B	108.4	C12—C11—C9	122.4 (2)
O2—C2—C1	108.3 (2)	C13—C12—C11	120.5 (2)
O2—C2—C3	109.75 (16)	C13—C12—H12A	119.7
C1—C2—C3	112.95 (19)	C11—C12—H12A	119.7
O2—C2—H2A	108.6	C14—C13—C12	120.1 (3)
C1—C2—H2A	108.6	C14—C13—H13A	119.9
C3—C2—H2A	108.6	C12—C13—H13A	119.9
O3—C3—C4	111.07 (18)	C13—C14—C15	120.1 (2)
O3—C3—C2	107.03 (16)	C13—C14—H14A	119.9
C4—C3—C2	109.23 (17)	C15—C14—H14A	119.9
O3—C3—H3A	109.8	C16—C15—C14	119.5 (3)
C4—C3—H3A	109.8	C16—C15—H15A	120.2
C2—C3—H3A	109.8	C14—C15—H15A	120.2
O4—C4—C5	112.53 (17)	C15—C16—C11	121.2 (3)
O4—C4—C3	107.68 (17)	C15—C16—H16A	119.4
C5—C4—C3	111.47 (19)	C11—C16—H16A	119.4
O4—C4—H4A	108.3	C26—C21—C22	117.3 (3)
C5—C4—H4A	108.3	C26—C21—C10	120.6 (3)
C3—C4—H4A	108.3	C22—C21—C10	122.1 (3)
O5—C5—C6	108.29 (18)	C23—C22—C21	120.6 (3)
O5—C5—C4	111.39 (17)	C23—C22—H22A	119.7
C6—C5—C4	109.87 (17)	C21—C22—H22A	119.7
O5—C5—H5A	109.1	C24—C23—C22	120.2 (3)
C6—C5—H5A	109.1	C24—C23—H23A	119.9
C4—C5—H5A	109.1	C22—C23—H23A	119.9
O2—C6—C5	111.32 (16)	C25—C24—C23	120.4 (3)
O2—C6—H6A	109.4	C25—C24—H24A	119.8
C5—C6—H6A	109.4	C23—C24—H24A	119.8
O2—C6—H6B	109.4	C24—C25—C26	120.0 (3)
C5—C6—H6B	109.4	C24—C25—H25A	120.0
H6A—C6—H6B	108.0	C26—C25—H25A	120.0
O3—C9—C11	110.49 (18)	C25—C26—C21	121.6 (3)
O3—C9—H9A	109.6	C25—C26—H26A	119.2
C11—C9—H9A	109.6	C21—C26—H26A	119.2
O3—C9—H9B	109.6
C10—O1—C1—C2	173.3 (2)	C3—O3—C9—C11	166.6 (2)
C6—O2—C2—C1	−173.07 (19)	C1—O1—C10—C21	−66.9 (4)
C6—O2—C2—C3	63.2 (2)	O3—C9—C11—C16	155.4 (3)
O1—C1—C2—O2	70.8 (2)	O3—C9—C11—C12	−26.4 (4)
O1—C1—C2—C3	−167.49 (18)	C16—C11—C12—C13	0.3 (4)
C9—O3—C3—C4	102.6 (2)	C9—C11—C12—C13	−177.8 (3)
C9—O3—C3—C2	−138.2 (2)	C11—C12—C13—C14	0.2 (5)
O2—C2—C3—O3	−178.27 (18)	C12—C13—C14—C15	−0.7 (5)
C1—C2—C3—O3	60.8 (2)	C13—C14—C15—C16	0.6 (5)
O2—C2—C3—C4	−57.9 (2)	C14—C15—C16—C11	0.0 (5)
C1—C2—C3—C4	−178.85 (19)	C12—C11—C16—C15	−0.4 (4)
O3—C3—C4—O4	−65.4 (2)	C9—C11—C16—C15	177.8 (3)
C2—C3—C4—O4	176.82 (17)	O1—C10—C21—C26	122.6 (3)
O3—C3—C4—C5	170.75 (16)	O1—C10—C21—C22	−58.1 (4)
C2—C3—C4—C5	52.9 (2)	C26—C21—C22—C23	1.1 (4)
O4—C4—C5—O5	−52.7 (2)	C10—C21—C22—C23	−178.3 (3)
C3—C4—C5—O5	68.4 (2)	C21—C22—C23—C24	0.2 (5)
O4—C4—C5—C6	−172.71 (18)	C22—C23—C24—C25	−0.5 (5)
C3—C4—C5—C6	−51.6 (2)	C23—C24—C25—C26	−0.4 (5)
C2—O2—C6—C5	−62.4 (2)	C24—C25—C26—C21	1.7 (5)
O5—C5—C6—O2	−66.5 (2)	C22—C21—C26—C25	−2.0 (4)
C4—C5—C6—O2	55.3 (2)	C10—C21—C26—C25	177.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5i	0.84	1.95	2.789 (2)	175
O5—H5···O2i	0.84	1.98	2.812 (2)	169
C1—H1A···O3	0.99	2.50	2.893 (3)	103
C6—H6B···O5ii	0.99	2.54	3.461 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O5i	0.84	1.95	2.789 (2)	175
O5—H5⋯O2i	0.84	1.98	2.812 (2)	169
C6—H6B⋯O5ii	0.99	2.54	3.461 (3)	155

Symmetry codes: (i) ; (ii) .