1-De­oxy-β-L-fructopyran­ose monohydrate

Although 1-de­oxy-L-fructose in aqueous solution consists of a mixture of the open-chain furan­ose and pyran­ose forms, it crystallizes solely as 1-de­oxy-β-L-fructopyran­ose mono­hydrate, C₆H₁₂O₆·H₂O. The absolute stereochemistry was determined by the use of L-rhamnitol as the starting material. There are no unusual crystal packing features.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.091
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.850     1.000
            Tmin(prime) and Tmax expected:      0.972     0.986
            RR(prime) =      0.862
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.86
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           29.94
           From the CIF: _reflns_number_total               1322
           Count of symmetry unique reflns         1344
           Completeness (_total/calc)             98.36%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and 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.

1-Deoxy-β-L-fructopyranose monohydrate

Crystal data

C6H14O6	Dx = 1.535 Mg m^−3
Mr = 182.17	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1879 reflections
a = 6.7824 (2) Å	θ = 5–30°
b = 9.6297 (3) Å	µ = 0.14 mm^−1
c = 12.0727 (5) Å	T = 150 K
V = 788.50 (5) Å^3	Hexagonal prism, colourless
Z = 4	0.20 × 0.20 × 0.10 mm
F(000) = 392

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	1107 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ω scans	θmax = 29.9°, θmin = 5.2°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −9→9
Tmin = 0.85, Tmax = 1.0	k = −13→12
6461 measured reflections	l = −16→16
1322 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.091	w = 1/[σ^2(F^2) + (0.05P)^2 + 0.03P], where P = [max(Fo^2,0) + 2Fc^2]/3
S = 0.92	(Δ/σ)max = 0.000189
1322 reflections	Δρmax = 0.28 e Å^−3
109 parameters	Δρmin = −0.26 e Å^−3
0 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5478 (3)	0.52100 (16)	0.64340 (14)	0.0147
C2	0.5134 (3)	0.41855 (16)	0.54761 (14)	0.0132
C3	0.3945 (3)	0.48479 (16)	0.45493 (13)	0.0155
C4	0.2018 (3)	0.54277 (17)	0.50093 (15)	0.0166
C5	0.2475 (3)	0.64180 (18)	0.59423 (16)	0.0205
O6	0.3575 (2)	0.57069 (13)	0.68030 (10)	0.0204
O7	0.0889 (2)	0.42754 (14)	0.53964 (12)	0.0296
O8	0.3593 (2)	0.37858 (12)	0.37415 (11)	0.0238
O9	0.69851 (18)	0.37122 (12)	0.50594 (11)	0.0174
O10	0.6621 (2)	0.63075 (12)	0.60222 (12)	0.0211
C11	0.6407 (3)	0.45224 (18)	0.74380 (14)	0.0179
O12	0.6412 (2)	0.22098 (12)	0.25787 (11)	0.0235
H21	0.4374	0.3387	0.5758	0.0171*
H31	0.4719	0.5625	0.4217	0.0194*
H41	0.1263	0.5923	0.4433	0.0203*
H51	0.1231	0.6769	0.6263	0.0258*
H52	0.3302	0.7198	0.5648	0.0246*
H111	0.6481	0.5182	0.8046	0.0282*
H112	0.7735	0.4212	0.7270	0.0275*
H113	0.5579	0.3724	0.7672	0.0278*
H6	0.2876	0.4084	0.3232	0.0359*
H8	0.6950	0.6781	0.6564	0.0321*
H12	−0.0246	0.4496	0.5217	0.0452*
H1	0.6631	0.1476	0.2938	0.0365*
H2	0.7148	0.2879	0.5223	0.0287*
H3	0.5739	0.2743	0.2996	0.0366*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0122 (8)	0.0164 (7)	0.0154 (8)	0.0017 (7)	0.0009 (7)	−0.0003 (7)
C2	0.0105 (8)	0.0130 (7)	0.0162 (9)	−0.0005 (6)	0.0024 (7)	−0.0011 (7)
C3	0.0180 (9)	0.0147 (7)	0.0138 (8)	−0.0002 (7)	−0.0017 (8)	−0.0015 (7)
C4	0.0129 (9)	0.0173 (7)	0.0196 (9)	0.0019 (7)	−0.0019 (8)	0.0055 (7)
C5	0.0234 (10)	0.0237 (8)	0.0145 (9)	0.0106 (8)	−0.0018 (9)	0.0001 (8)
O6	0.0183 (7)	0.0283 (6)	0.0147 (6)	0.0107 (6)	0.0007 (6)	0.0014 (6)
O7	0.0140 (7)	0.0301 (7)	0.0446 (9)	−0.0038 (6)	−0.0050 (7)	0.0184 (7)
O8	0.0283 (8)	0.0211 (6)	0.0220 (7)	0.0060 (6)	−0.0114 (6)	−0.0063 (5)
O9	0.0134 (7)	0.0169 (6)	0.0219 (7)	0.0035 (5)	0.0023 (6)	−0.0009 (5)
O10	0.0293 (8)	0.0169 (6)	0.0170 (6)	−0.0087 (6)	−0.0038 (6)	0.0006 (5)
C11	0.0157 (9)	0.0228 (8)	0.0153 (8)	0.0019 (8)	−0.0023 (8)	0.0028 (7)
O12	0.0293 (8)	0.0206 (6)	0.0205 (7)	0.0017 (6)	0.0054 (7)	0.0031 (6)

Geometric parameters (Å, º)

C1—C2	1.538 (2)	C5—O6	1.451 (2)
C1—O6	1.447 (2)	C5—H51	0.988
C1—O10	1.4019 (19)	C5—H52	1.003
C1—C11	1.518 (2)	O7—H12	0.827
C2—C3	1.519 (2)	O8—H6	0.835
C2—O9	1.427 (2)	O9—H2	0.834
C2—H21	0.986	O10—H8	0.828
C3—C4	1.526 (3)	C11—H111	0.973
C3—O8	1.4332 (18)	C11—H112	0.970
C3—H31	0.998	C11—H113	0.993
C4—C5	1.508 (3)	O12—H1	0.842
C4—O7	1.427 (2)	O12—H3	0.852
C4—H41	0.987
C2—C1—O6	107.97 (14)	C3—C4—H41	111.4
C2—C1—O10	107.50 (14)	C5—C4—H41	109.1
O6—C1—O10	110.68 (12)	O7—C4—H41	109.2
C2—C1—C11	112.55 (13)	C4—C5—O6	110.01 (14)
O6—C1—C11	105.59 (13)	C4—C5—H51	109.5
O10—C1—C11	112.48 (14)	O6—C5—H51	108.7
C1—C2—C3	111.40 (12)	C4—C5—H52	108.9
C1—C2—O9	109.67 (14)	O6—C5—H52	108.7
C3—C2—O9	109.96 (14)	H51—C5—H52	111.1
C1—C2—H21	108.6	C5—O6—C1	113.21 (14)
C3—C2—H21	107.7	C4—O7—H12	102.4
O9—C2—H21	109.4	C3—O8—H6	110.7
C2—C3—C4	109.88 (14)	C2—O9—H2	109.9
C2—C3—O8	106.85 (12)	C1—O10—H8	106.5
C4—C3—O8	111.46 (15)	C1—C11—H111	109.9
C2—C3—H31	109.4	C1—C11—H112	110.6
C4—C3—H31	108.8	H111—C11—H112	108.2
O8—C3—H31	110.4	C1—C11—H113	109.3
C3—C4—C5	109.08 (15)	H111—C11—H113	108.7
C3—C4—O7	107.13 (13)	H112—C11—H113	110.2
C5—C4—O7	110.95 (15)	H1—O12—H3	107.2

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H12···O9^i	0.83	2.03	2.733 (2)	142
O8—H6···O6^ii	0.84	2.00	2.807 (2)	163
O9—H2···O7^iii	0.83	2.36	3.022 (2)	136
O9—H2···O8^iii	0.83	2.26	3.012 (2)	151
O10—H8···O12^iv	0.83	1.92	2.711 (2)	160
O12—H1···O6^iii	0.84	2.50	3.256 (2)	150
O12—H1···O7^iii	0.84	2.20	2.854 (2)	135
O12—H3···O8	0.85	1.98	2.816 (2)	165

Symmetry codes: (i) x−1, y, z; (ii) −x+1/2, −y+1, z−1/2; (iii) x+1/2, −y+1/2, −z+1; (iv) −x+3/2, −y+1, z+1/2.