1-De-oxy-l-mannitol (6-de-oxy-l-mannitol or l-rhamnitol).

The crystalline form of 1-de-oxy-l-mannitol, C(6)H(14)O(5), exists as an extensively hydrogen-bonded structure with each mol-ecule acting as a donor and acceptor for five hydrogen bonds. There are no unusual crystal-packing features; the absolute configuration was determined from the use of 6-de-oxy-l-mannose (l-rhamnose) as the starting material.

Related literature

For related literature see: Jenkinson et al. (2008 ▶); Gullapalli et al. (2007 ▶); Izumori (2002 ▶, 2006 ▶); Granstrom et al. (2004 ▶); Beadle et al. (1992 ▶); Skytte (2002 ▶); Sui et al. (2005 ▶); Levin (2002 ▶); Howling & Callagan (2000 ▶); Bertelsen et al. (1999 ▶); Takata et al. (2005 ▶); Menavuvu et al. (2006 ▶); Hossain et al. (2006 ▶); Donner et al. (1999 ▶).

Experimental

Crystal data

C6H14O5

M = 166.17

Orthorhombic,

a = 7.3650 (3) Å

b = 7.6272 (3) Å

c = 13.7676 (5) Å

V = 773.39 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 150 K

0.40 × 0.40 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.89, T max = 0.99

5170 measured reflections

1033 independent reflections

974 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.072

S = 0.97

1033 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024586/lh2670sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024586/lh2670Isup2.hkl

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

C6H14O5	F000 = 360
Mr = 166.17	Dx = 1.427 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1002 reflections
a = 7.3650 (3) Å	θ = 5–27º
b = 7.6272 (3) Å	µ = 0.12 mm−1
c = 13.7676 (5) Å	T = 150 K
V = 773.39 (5) Å3	Plate, colourless
Z = 4	0.40 × 0.40 × 0.10 mm

Nonius KappaCCD diffractometer	974 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
T = 150 K	θmax = 27.5º
ω scans	θmin = 5.2º
Absorption correction: multi-scan(DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −9→9
Tmin = 0.89, Tmax = 0.99	k = −9→9
5170 measured reflections	l = −17→17
1033 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027	w = 1/[σ2(F2) + (0.04P)2 + 0.19P], where P = [max(Fo2,0) + 2Fc2]/3
wR(F2) = 0.072	(Δ/σ)max = 0.0003
S = 0.97	Δρmax = 0.24 e Å−3
1033 reflections	Δρmin = −0.19 e Å−3
100 parameters	Extinction correction: None
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	0.45760 (15)	0.66827 (14)	0.58528 (7)	0.0158
C2	0.5038 (2)	0.53406 (18)	0.51734 (10)	0.0121
C3	0.4654 (2)	0.35710 (19)	0.56608 (11)	0.0129
O4	0.51432 (16)	0.21669 (13)	0.50177 (8)	0.0180
C5	0.5694 (2)	0.3334 (2)	0.65961 (11)	0.0160
O6	0.76010 (15)	0.34756 (16)	0.64310 (8)	0.0190
C7	0.3954 (2)	0.55797 (19)	0.42326 (11)	0.0125
O8	0.20579 (15)	0.57629 (14)	0.44513 (8)	0.0163
C9	0.4543 (2)	0.7196 (2)	0.36498 (10)	0.0140
O10	0.63971 (16)	0.69611 (16)	0.33563 (8)	0.0188
C11	0.3428 (3)	0.7388 (2)	0.27300 (11)	0.0195
H21	0.6338	0.5422	0.5017	0.0146*
H31	0.3366	0.3507	0.5836	0.0149*
H51	0.5258	0.4239	0.7048	0.0180*
H52	0.5424	0.2171	0.6890	0.0191*
H71	0.4147	0.4569	0.3816	0.0137*
H91	0.4402	0.8236	0.4059	0.0171*
H111	0.3791	0.8390	0.2343	0.0290*
H112	0.2112	0.7500	0.2863	0.0299*
H113	0.3580	0.6334	0.2330	0.0284*
H1	0.7159	0.7532	0.3689	0.0319*
H2	0.4249	0.1898	0.4627	0.0307*
H3	0.1795	0.4708	0.4542	0.0290*
H4	0.8002	0.3523	0.7025	0.0312*
H5	0.5310	0.7560	0.5771	0.0285*

	U11	U22	U33	U12	U13	U23
O1	0.0168 (6)	0.0130 (5)	0.0175 (5)	−0.0022 (4)	0.0027 (5)	−0.0036 (4)
C2	0.0103 (7)	0.0137 (6)	0.0122 (6)	0.0004 (6)	0.0007 (6)	−0.0009 (5)
C3	0.0118 (7)	0.0125 (6)	0.0145 (7)	0.0011 (6)	0.0000 (6)	0.0014 (5)
O4	0.0207 (6)	0.0137 (5)	0.0198 (5)	0.0040 (5)	−0.0064 (5)	−0.0030 (4)
C5	0.0146 (8)	0.0191 (7)	0.0144 (7)	0.0011 (6)	0.0020 (6)	0.0022 (6)
O6	0.0144 (6)	0.0283 (6)	0.0142 (5)	0.0026 (5)	−0.0015 (4)	−0.0002 (4)
C7	0.0103 (7)	0.0127 (7)	0.0146 (7)	0.0004 (5)	0.0003 (6)	−0.0003 (6)
O8	0.0102 (5)	0.0128 (5)	0.0259 (6)	0.0000 (4)	−0.0005 (4)	0.0033 (4)
C9	0.0130 (7)	0.0143 (6)	0.0148 (7)	−0.0010 (6)	0.0003 (6)	0.0017 (6)
O10	0.0120 (6)	0.0284 (6)	0.0160 (5)	−0.0049 (5)	0.0009 (4)	−0.0020 (5)
C11	0.0173 (8)	0.0250 (8)	0.0163 (7)	0.0002 (7)	−0.0017 (6)	0.0065 (6)

O1—C2	1.4277 (17)	O6—H4	0.870
O1—H5	0.868	C7—O8	1.4354 (18)
C2—C3	1.5335 (19)	C7—C9	1.533 (2)
C2—C7	1.5323 (19)	C7—H71	0.971
C2—H21	0.983	O8—H3	0.837
C3—O4	1.4354 (18)	C9—O10	1.4352 (19)
C3—C5	1.509 (2)	C9—C11	1.516 (2)
C3—H31	0.980	C9—H91	0.979
O4—H2	0.875	O10—H1	0.845
C5—O6	1.4269 (18)	C11—H111	0.969
C5—H51	0.983	C11—H112	0.991
C5—H52	0.995	C11—H113	0.981
C2—O1—H5	108.6	C2—C7—O8	109.94 (12)
O1—C2—C3	107.49 (11)	C2—C7—C9	112.99 (12)
O1—C2—C7	110.15 (12)	O8—C7—C9	107.87 (12)
C3—C2—C7	112.26 (12)	C2—C7—H71	109.2
O1—C2—H21	109.3	O8—C7—H71	110.1
C3—C2—H21	109.3	C9—C7—H71	106.7
C7—C2—H21	108.4	C7—O8—H3	99.4
C2—C3—O4	109.91 (11)	C7—C9—O10	108.44 (13)
C2—C3—C5	112.67 (12)	C7—C9—C11	111.20 (12)
O4—C3—C5	108.04 (12)	O10—C9—C11	106.98 (12)
C2—C3—H31	109.3	C7—C9—H91	108.7
O4—C3—H31	111.0	O10—C9—H91	111.4
C5—C3—H31	105.9	C11—C9—H91	110.2
C3—O4—H2	111.5	C9—O10—H1	114.5
C3—C5—O6	110.76 (12)	C9—C11—H111	112.7
C3—C5—H51	106.9	C9—C11—H112	112.6
O6—C5—H51	111.7	H111—C11—H112	107.7
C3—C5—H52	110.6	C9—C11—H113	109.2
O6—C5—H52	109.2	H111—C11—H113	107.8
H51—C5—H52	107.6	H112—C11—H113	106.6
C5—O6—H4	100.8

D—H···A	D—H	H···A	D···A	D—H···A
O10—H1···O1i	0.85	1.98	2.782 (2)	158
O4—H2···O6ii	0.87	1.92	2.779 (2)	168
O8—H3···O4ii	0.84	1.97	2.742 (2)	152
O6—H4···O10iii	0.87	1.92	2.772 (2)	165
O1—H5···O8i	0.87	1.84	2.704 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10—H1⋯O1i	0.85	1.98	2.782 (2)	158
O4—H2⋯O6ii	0.87	1.92	2.779 (2)	168
O8—H3⋯O4ii	0.84	1.97	2.742 (2)	152
O6—H4⋯O10iii	0.87	1.92	2.772 (2)	165
O1—H5⋯O8i	0.87	1.84	2.704 (2)	173

Symmetry codes: (i) ; (ii) ; (iii) .