Literature DB >> 21583239

α-d-Tagatopyran-ose.

Francesco Punzo, David J Watkin, George W J Fleet.

Abstract

The title compound, C(6)H(12)O(6), also known as d-Tagatose, occurs in its furanose and pyranose forms in solution, but only the α-pyran-ose form crystallizes out. In the crystal, the molecules form hydrogen bonded chains propagating in [100] linked by O-H⋯O interactions. Further O-H⋯O bonds cross-link the chains.

Entities: Chemical Disease Gene Species

Year: 2009 PMID： 21583239 PMCID： PMC2969552 DOI： 10.1107/S1600536809017656

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the d-tagatose market price, syntheses and applications, see: Angyal (1991 ▶); Beadle et al. (1992 ▶); Granstrom et al. (2004 ▶); Izumori (2002 ▶); Skytte (2002 ▶); Porwell (2007 ▶). For the potential of the title compound as a chiral building block, see: Soengas et al. (2005 ▶); Jones et al. (2007 ▶, 2008 ▶); Yoshihara et al. (2008 ▶). For related crystallographic literature, see: Takagi et al. (1969 ▶); Görbitz (1999 ▶); Watkin et al. (2005 ▶); Kwiecien et al. (2008 ▶); Larson (1970 ▶).

Experimental

Crystal data

C6H12O6 M = 180.16 Orthorhombic, a = 6.2201 (1) Å b = 6.5022 (1) Å c = 17.6629 (4) Å V = 714.36 (2) Å3 Z = 4 Mo Kα radiation μ = 0.15 mm−1 T = 190 K 0.50 × 0.30 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.96, T max = 0.97 2343 measured reflections 1378 independent reflections 1351 reflections with I > 2.0σ(I) R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.025 wR(F 2) = 0.065 S = 0.96 1378 reflections 110 parameters H-atom parameters constrained Δρmax = 0.34 e Å−3 Δρmin = −0.20 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/S1600536809017656/fl2248sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017656/fl2248Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₆H₁₂O₆	F(000) = 384
M_r = 180.16	D_x = 1.675 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1344 reflections
a = 6.2201 (1) Å	θ = 5–32°
b = 6.5022 (1) Å	µ = 0.15 mm⁻¹
c = 17.6629 (4) Å	T = 190 K
V = 714.36 (2) Å³	Prism, colourless
Z = 4	0.50 × 0.30 × 0.20 mm

Nonius KappaCCD diffractometer	1351 reflections with I > 2.0σ(I)
graphite	R_int = 0.010
ω scans	θ_max = 31.5°, θ_min = 5.6°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −9→9
T_min = 0.96, T_max = 0.97	k = −9→9
2343 measured reflections	l = −25→25
1378 independent reflections

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.025	Method = Modified Sheldrick w = 1/[σ²(F²) + ( 0.04P)² + 0.18P], where P = (max(F_o²,0) + 2F_c²)/3
wR(F²) = 0.065	(Δ/σ)_max = 0.0001
S = 0.97	Δρ_max = 0.34 e Å⁻³
1378 reflections	Δρ_min = −0.20 e Å⁻³
110 parameters	Extinction correction: Larson (1970), Equation 22
0 restraints	Extinction coefficient: 260 (40)
Primary atom site location: structure-invariant direct methods

	x	y	z	U_iso*/U_eq
O1	−0.20580 (13)	0.34108 (12)	0.17994 (4)	0.0157
C2	−0.02883 (15)	0.29006 (15)	0.13171 (5)	0.0113
C3	0.10689 (16)	0.47890 (15)	0.11569 (5)	0.0118
O4	−0.02429 (12)	0.62640 (12)	0.07662 (4)	0.0150
C5	0.29501 (17)	0.41697 (16)	0.06531 (6)	0.0143
O6	0.42202 (12)	0.25811 (12)	0.09985 (4)	0.0139
C7	0.30499 (16)	0.07510 (15)	0.11774 (5)	0.0118
C8	0.11083 (16)	0.12491 (15)	0.16890 (5)	0.0118
O9	0.18387 (14)	0.19838 (12)	0.24031 (4)	0.0171
O10	0.22054 (13)	−0.01458 (12)	0.05105 (4)	0.0142
C11	0.46654 (17)	−0.06848 (16)	0.15537 (6)	0.0155
O12	0.61351 (15)	−0.12797 (16)	0.09805 (5)	0.0271
H21	−0.0851	0.2365	0.0849	0.0134*
H31	0.1585	0.5338	0.1629	0.0151*
H51	0.3943	0.5322	0.0579	0.0174*
H52	0.2364	0.3698	0.0173	0.0181*
H81	0.0263	0.0023	0.1724	0.0147*
H112	0.5375	−0.0021	0.1979	0.0193*
H111	0.3929	−0.1876	0.1738	0.0194*
H41	0.0463	0.7255	0.0642	0.0240*
H91	0.1860	0.0956	0.2678	0.0275*
H121	0.7044	−0.2120	0.1130	0.0413*
H101	0.3225	−0.0416	0.0248	0.0252*
H11	−0.3163	0.3242	0.1565	0.0238*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0103 (3)	0.0192 (4)	0.0177 (3)	−0.0009 (3)	0.0026 (3)	−0.0047 (3)
C2	0.0102 (4)	0.0120 (4)	0.0118 (4)	−0.0005 (4)	0.0005 (3)	−0.0019 (3)
C3	0.0107 (4)	0.0107 (4)	0.0141 (4)	0.0001 (3)	−0.0003 (3)	0.0004 (3)
O4	0.0131 (3)	0.0119 (3)	0.0201 (3)	0.0026 (3)	−0.0007 (3)	0.0027 (3)
C5	0.0125 (4)	0.0121 (4)	0.0183 (4)	0.0022 (4)	0.0034 (4)	0.0041 (3)
O6	0.0097 (3)	0.0111 (3)	0.0209 (3)	−0.0001 (3)	−0.0007 (3)	0.0036 (3)
C7	0.0112 (4)	0.0100 (4)	0.0143 (4)	−0.0003 (4)	−0.0007 (3)	0.0007 (3)
C8	0.0124 (4)	0.0107 (4)	0.0122 (4)	−0.0020 (4)	−0.0001 (3)	−0.0004 (3)
O9	0.0243 (4)	0.0154 (3)	0.0115 (3)	−0.0007 (3)	−0.0033 (3)	0.0001 (3)
O10	0.0138 (3)	0.0151 (3)	0.0137 (3)	0.0009 (3)	0.0005 (3)	−0.0030 (3)
C11	0.0136 (4)	0.0139 (4)	0.0191 (4)	0.0026 (4)	−0.0015 (4)	0.0033 (4)
O12	0.0213 (4)	0.0322 (5)	0.0280 (4)	0.0161 (4)	0.0044 (4)	0.0078 (4)

O1—C2	1.4309 (12)	O6—C7	1.4303 (12)
O1—H11	0.810	C7—C8	1.5426 (14)
C2—C3	1.5167 (14)	C7—O10	1.4155 (12)
C2—C8	1.5294 (14)	C7—C11	1.5241 (14)
C2—H21	0.963	C8—O9	1.4232 (11)
C3—O4	1.4359 (12)	C8—H81	0.957
C3—C5	1.5241 (14)	O9—H91	0.826
C3—H31	0.963	O10—H101	0.805
O4—H41	0.810	C11—O12	1.4178 (14)
C5—O6	1.4364 (12)	C11—H112	0.973
C5—H51	0.980	C11—H111	0.957
C5—H52	0.972	O12—H121	0.829

C2—O1—H11	108.5	O6—C7—C8	110.68 (8)
O1—C2—C3	110.58 (8)	O6—C7—O10	110.35 (8)
O1—C2—C8	110.13 (8)	C8—C7—O10	106.46 (8)
C3—C2—C8	109.41 (8)	O6—C7—C11	105.69 (8)
O1—C2—H21	108.4	C8—C7—C11	112.92 (8)
C3—C2—H21	109.6	O10—C7—C11	110.81 (8)
C8—C2—H21	108.7	C7—C8—C2	109.91 (8)
C2—C3—O4	108.31 (8)	C7—C8—O9	109.85 (8)
C2—C3—C5	108.81 (8)	C2—C8—O9	109.04 (8)
O4—C3—C5	109.40 (8)	C7—C8—H81	107.0
C2—C3—H31	108.9	C2—C8—H81	107.5
O4—C3—H31	111.0	O9—C8—H81	113.5
C5—C3—H31	110.3	C8—O9—H91	104.7
C3—O4—H41	110.7	C7—O10—H101	106.1
C3—C5—O6	111.36 (8)	C7—C11—O12	106.31 (8)
C3—C5—H51	111.1	C7—C11—H112	111.4
O6—C5—H51	105.1	O12—C11—H112	112.4
C3—C5—H52	107.7	C7—C11—H111	109.2
O6—C5—H52	110.4	O12—C11—H111	109.3
H51—C5—H52	111.2	H112—C11—H111	108.3
C5—O6—C7	114.34 (8)	C11—O12—H121	113.0

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O10ⁱ	0.81	2.02	2.8236 (14)	171
O9—H91···O1ⁱⁱ	0.83	1.90	2.7203 (14)	173
O12—H121···O4ⁱⁱⁱ	0.83	2.09	2.7875 (14)	142
O10—H101···O4^iv	0.81	2.10	2.8518 (14)	155
O1—H11···O6^v	0.81	1.96	2.7661 (14)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H41⋯O10ⁱ	0.81	2.02	2.8236 (14)	171
O9—H91⋯O1ⁱⁱ	0.83	1.90	2.7203 (14)	173
O12—H121⋯O4ⁱⁱⁱ	0.83	2.09	2.7875 (14)	142
O10—H101⋯O4^iv	0.81	2.10	2.8518 (14)	155
O1—H11⋯O6^v	0.81	1.96	2.7661 (14)	175

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

4 in total

1. What is the best crystal size for collection of X-ray data? Refinement of the structure of glycyl-L-serine based on data from a very large crystal.

Authors:
Journal: Acta Crystallogr B Date: 1999-12-01