1-De-oxy-d-arabinitol.

Addition of methyl lithium to d-erythrono-1,4-lactone followed by acid deprotection was shown, by X-ray crystallography, to give 1-de-oxy-d-arabinitol, C(5)H(12)O(4), rather than 1-de-oxy-d-ribitol as the major product. The crystal structure exists as hydrogen-bonded chains of mol-ecules running parallel to the c axis which are further linked together by hydrogen bonds. Each mol-ecule is a donor and an acceptor for four hydrogen bonds.

Related literature

For related literature see: Izumori (2002 ▶, 2006 ▶); Granstrom et al. (2004 ▶); Beadle et al. (1992 ▶); Skytte (2002 ▶); Levin (2002 ▶); Howling & Callagan (2000 ▶); Bertelsen et al. (1999 ▶); Takata et al. (2005 ▶); Menavuvu et al. (2006 ▶); Sui et al. (2005 ▶); Hossain et al. (2006 ▶); Zehner et al. (1994 ▶); Donner et al. (1999 ▶); Yoshihara et al. (2008 ▶); Takai & Heathcock (1985 ▶); Zissis & Richtmyer (1954 ▶).

Experimental

Crystal data

C5H12O4

M = 136.15

Tetragonal,

a = 12.9873 (5) Å

c = 8.3679 (3) Å

V = 1411.41 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 150 K

0.25 × 0.25 × 0.25 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.93, T max = 0.97

3189 measured reflections

855 independent reflections

750 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.00

855 reflections

82 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.39 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/S1600536808012555/lh2622sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012555/lh2622Isup2.hkl

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

C5H12O4	Z = 8
Mr = 136.15	F000 = 592
Tetragonal, I41	Dx = 1.281 Mg m−3
Hall symbol: I 4bw	Mo Kα radiation λ = 0.71073 Å
a = 12.9873 (5) Å	Cell parameters from 815 reflections
b = 12.9873 (5) Å	θ = 5–27º
c = 8.3679 (3) Å	µ = 0.11 mm−1
α = 90º	T = 150 K
β = 90º	Block, colourless
γ = 90º	0.25 × 0.25 × 0.25 mm
V = 1411.41 (9) Å3

Nonius KappaCCD area-detector diffractometer	750 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 150 K	θmax = 27.5º
ω scans	θmin = 5.3º
Absorption correction: multi-scan(DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −16→16
Tmin = 0.93, Tmax = 0.97	k = −11→11
3189 measured reflections	l = −10→10
855 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(F2) + ( 0.07P)2 + 1.26P], where P = (max(Fo2,0) + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.002
855 reflections	Δρmax = 0.34 e Å−3
82 parameters	Δρmin = −0.39 e Å−3
1 restraint	Extinction correction: None

	x	y	z	Uiso*/Ueq
O1	0.64776 (13)	0.51955 (15)	0.6622 (3)	0.0211
C2	0.75127 (18)	0.5139 (2)	0.6068 (4)	0.0186
C3	0.7537 (2)	0.4842 (2)	0.4296 (4)	0.0187
O4	0.85700 (13)	0.48073 (16)	0.3723 (3)	0.0237
C5	0.6897 (2)	0.5564 (2)	0.3268 (4)	0.0235
O6	0.73116 (15)	0.65798 (14)	0.3242 (3)	0.0250
C7	0.8135 (2)	0.4417 (2)	0.7135 (4)	0.0208
O8	0.76689 (14)	0.34124 (13)	0.7126 (3)	0.0216
C9	0.8162 (3)	0.4788 (2)	0.8844 (4)	0.0371
H21	0.7853	0.5822	0.6286	0.0184*
H31	0.7208	0.4168	0.4126	0.0196*
H51	0.6985	0.5315	0.2238	0.0277*
H52	0.6191	0.5542	0.3475	0.0271*
H71	0.8827	0.4379	0.6604	0.0259*
H91	0.8413	0.4265	0.9544	0.0541*
H92	0.8595	0.5396	0.8958	0.0548*
H93	0.7474	0.4971	0.9202	0.0552*
H1	0.6194	0.4722	0.5703	0.0308*
H8	0.7975	0.2944	0.6379	0.0334*
H6	0.7418	0.6761	0.4388	0.0359*
H4	0.9070	0.5369	0.3651	0.0365*

	U11	U22	U33	U12	U13	U23
O1	0.0197 (10)	0.0197 (9)	0.0240 (12)	0.0010 (7)	0.0042 (9)	−0.0023 (9)
C2	0.0139 (13)	0.0193 (12)	0.0225 (16)	−0.0037 (9)	0.0006 (12)	−0.0001 (13)
C3	0.0176 (14)	0.0167 (12)	0.0218 (17)	−0.0006 (9)	−0.0011 (12)	0.0010 (13)
O4	0.0169 (9)	0.0213 (9)	0.0329 (14)	0.0015 (7)	0.0061 (10)	0.0035 (10)
C5	0.0223 (14)	0.0269 (15)	0.0214 (16)	0.0014 (11)	0.0013 (13)	0.0032 (15)
O6	0.0308 (11)	0.0215 (10)	0.0227 (12)	0.0025 (8)	0.0056 (11)	0.0046 (10)
C7	0.0201 (13)	0.0204 (13)	0.0218 (16)	−0.0035 (10)	−0.0045 (13)	−0.0004 (13)
O8	0.0254 (10)	0.0189 (10)	0.0204 (12)	0.0010 (7)	0.0049 (10)	0.0000 (9)
C9	0.053 (2)	0.0332 (16)	0.0253 (15)	−0.0023 (15)	−0.0149 (15)	−0.0036 (13)

O1—C2	1.424 (3)	C5—H51	0.927
O1—H1	1.051	C5—H52	0.934
C2—C3	1.532 (3)	O6—H6	0.997
C2—C7	1.527 (4)	C7—O8	1.438 (3)
C2—H21	1.008	C7—C9	1.510 (5)
C3—O4	1.425 (3)	C7—H71	1.004
C3—C5	1.520 (4)	O8—H8	0.959
C3—H31	0.985	C9—H91	0.954
O4—H4	0.978	C9—H92	0.974
C5—O6	1.425 (3)	C9—H93	0.972
C2—O1—H1	93.6	C3—C5—H52	114.4
O1—C2—C3	110.4 (2)	O6—C5—H52	113.8
O1—C2—C7	109.9 (3)	H51—C5—H52	106.4
C3—C2—C7	113.6 (2)	C5—O6—H6	104.9
O1—C2—H21	108.0	C2—C7—O8	109.4 (2)
C3—C2—H21	112.9	C2—C7—C9	111.7 (2)
C7—C2—H21	101.7	O8—C7—C9	107.7 (3)
C2—C3—O4	110.7 (2)	C2—C7—H71	104.2
C2—C3—C5	112.4 (2)	O8—C7—H71	109.3
O4—C3—C5	110.1 (2)	C9—C7—H71	114.4
C2—C3—H31	110.8	C7—O8—H8	113.9
O4—C3—H31	109.4	C7—C9—H91	111.2
C5—C3—H31	103.2	C7—C9—H92	111.4
C3—O4—H4	128.4	H91—C9—H92	108.7
C3—C5—O6	111.9 (2)	C7—C9—H93	110.4
C3—C5—H51	104.0	H91—C9—H93	107.4
O6—C5—H51	105.2	H92—C9—H93	107.6

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O8i	0.96	1.76	2.698 (4)	164
O6—H6···O6ii	1.00	1.98	2.712 (4)	128
O4—H4···O1iii	0.98	1.77	2.718 (4)	162
O1—H1···O4iv	1.05	2.03	2.712 (3)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯O8i	0.96	1.76	2.698 (4)	164
O6—H6⋯O6ii	1.00	1.98	2.712 (4)	128
O4—H4⋯O1iii	0.98	1.77	2.718 (4)	162
O1—H1⋯O4iv	1.05	2.03	2.712 (3)	120

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