Crystal structure of β-d,l-fructose.

The title compound, C6H12O6, was crystallized from an aqueous solution of equimolar mixture of d- and l-fructose (1,3,4,5,6-penta-hydroxy-hexan-2-one, arabino-hexulose or levu-lose), and it was confirmed that d-fructose (or l-fructose) formed β-pyran-ose with a (2) C 5 (or (5) C 2) conformation. In the crystal, two O-H⋯O hydrogen bonds between the hy-droxy groups at the C-1 and C-3 positions, and at the C-4 and C-5 positions connect homochiral mol-ecules into a column along the a axis. The columns are linked by other O-H⋯O hydrogen bonds between d- and l-fructose mol-ecules, forming a three-dimensional network.

Related literature

For crystal structures of chiral β-d-fructose, racemic β-d,l-allose and racemic β-d,l-psicose, see: Kanters et al. (1977 ▸); Ishii, Senoo et al. (2015 ▸); Ishii, Sakane et al. (2015 ▸), respectively. For the synthesis of chiral l-fructose, see: Itoh & Izumori (1996 ▸).

Experimental

Crystal data

C6H12O6

M = 180.16

Triclinic,

a = 5.43124 (19) Å

b = 7.2727 (3) Å

c = 10.1342 (4) Å

α = 69.120 (2)°

β = 83.907 (2)°

γ = 78.381 (2)°

V = 366.09 (2) Å3

Z = 2

Cu Kα radiation

μ = 1.30 mm−1

T = 296 K

0.10 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ▸) T min = 0.729, T max = 0.878

6710 measured reflections

1329 independent reflections

1211 reflections with F 2 > 2.0σ(F 2)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.095

S = 1.08

1329 reflections

115 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.23 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2009 ▸); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SIR2011 (Burla et al., 2012 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: CrystalStructure (Rigaku, 2014 ▸); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015016503/is5416sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015016503/is5416Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015016503/is5416Isup3.cml

Click here for additional data file.

ORTEP . DOI: 10.1107/S2056989015016503/is5416fig1.tif

ORTEP view of the title compound with the atom-labeling scheme. The thermal ellipsoids of all non-hydrogen atoms are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

Click here for additional data file.

c . DOI: 10.1107/S2056989015016503/is5416fig2.tif

Part of the packing diagram of the title compound viewed down the c-axis, showing the hydrogen-bonding network (green solid lines).

Click here for additional data file.

a . DOI: 10.1107/S2056989015016503/is5416fig3.tif

Part of the packing diagram of the title compound viewed down the a-axis, showing the hydrogen-bonding network (green solid lines).

CCDC reference: 1422317

Additional supporting information: crystallographic information; 3D view; checkCIF report

C6H12O6	Z = 2
Mr = 180.16	F(000) = 192.00
Triclinic, P1	Dx = 1.634 Mg m−3
a = 5.43124 (19) Å	Cu Kα radiation, λ = 1.54187 Å
b = 7.2727 (3) Å	Cell parameters from 4534 reflections
c = 10.1342 (4) Å	θ = 4.7–68.4°
α = 69.120 (2)°	µ = 1.30 mm−1
β = 83.907 (2)°	T = 296 K
γ = 78.381 (2)°	Block, colorless
V = 366.09 (2) Å3	0.10 × 0.10 × 0.10 mm

Rigaku R-AXIS RAPID diffractometer	1211 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.000 pixels mm-1	Rint = 0.079
ω scans	θmax = 68.2°, θmin = 4.7°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −6→6
Tmin = 0.729, Tmax = 0.878	k = −8→8
6710 measured reflections	l = −12→12
1329 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0374P)2 + 0.1404P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1329 reflections	Δρmax = 0.32 e Å−3
115 parameters	Δρmin = −0.23 e Å−3
0 restraints	Extinction correction: SHELXL2013 (Sheldrick, 2015)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.125 (6)
Secondary atom site location: difference Fourier map

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
O1	1.19555 (19)	0.09152 (15)	0.87814 (12)	0.0325 (3)
O2	0.66671 (18)	0.27440 (15)	0.92243 (11)	0.0287 (3)
O3	0.50386 (19)	0.33842 (16)	0.65941 (12)	0.0294 (3)
O4	0.34223 (18)	0.76120 (15)	0.58108 (11)	0.0264 (3)
O5	0.81908 (18)	0.84537 (14)	0.60893 (12)	0.0290 (3)
O6	0.96847 (17)	0.47716 (14)	0.82413 (11)	0.0223 (3)
C1	1.0136 (3)	0.1818 (2)	0.77318 (17)	0.0265 (4)
C2	0.8236 (2)	0.34747 (19)	0.80373 (15)	0.0195 (3)
C3	0.6557 (2)	0.46432 (19)	0.67791 (15)	0.0190 (3)
C4	0.4906 (3)	0.6455 (2)	0.70256 (15)	0.0200 (3)
C5	0.6558 (3)	0.77295 (19)	0.72899 (16)	0.0223 (3)
C6	0.8182 (3)	0.6457 (2)	0.85210 (16)	0.0254 (4)
H1A	1.30779	0.15812	0.86062	0.0390*
H1C	0.92594	0.08085	0.76811	0.0318*
H1B	1.0976	0.23653	0.68208	0.0318*
H2A	0.74136	0.16995	0.97716	0.0345*
H3A	0.55367	0.31042	0.58847	0.0353*
H3B	0.76216	0.5097	0.59244	0.0227*
H4A	0.19353	0.75392	0.60178	0.0317*
H4B	0.37832	0.60041	0.78545	0.0240*
H5A	0.74552	0.94902	0.55285	0.0348*
H5B	0.55062	0.8858	0.75058	0.0268*
H6A	0.92669	0.72507	0.86923	0.0305*
H6B	0.71231	0.59981	0.93633	0.0305*

	U11	U22	U33	U12	U13	U23
O1	0.0202 (6)	0.0153 (5)	0.0465 (8)	−0.0003 (4)	−0.0014 (5)	0.0066 (5)
O2	0.0251 (6)	0.0190 (5)	0.0265 (6)	0.0006 (4)	0.0037 (5)	0.0074 (4)
O3	0.0292 (6)	0.0280 (6)	0.0361 (7)	−0.0153 (5)	−0.0002 (5)	−0.0118 (5)
O4	0.0160 (5)	0.0236 (6)	0.0298 (6)	−0.0001 (4)	−0.0051 (4)	0.0019 (5)
O5	0.0208 (5)	0.0154 (5)	0.0385 (7)	−0.0035 (4)	−0.0014 (5)	0.0060 (5)
O6	0.0186 (5)	0.0164 (5)	0.0309 (6)	−0.0004 (4)	−0.0061 (4)	−0.0071 (4)
C1	0.0223 (7)	0.0144 (7)	0.0389 (9)	−0.0022 (6)	−0.0001 (6)	−0.0054 (6)
C2	0.0176 (7)	0.0123 (6)	0.0242 (8)	−0.0039 (5)	0.0003 (6)	−0.0007 (5)
C3	0.0177 (7)	0.0140 (7)	0.0233 (8)	−0.0070 (5)	−0.0006 (6)	−0.0020 (6)
C4	0.0158 (7)	0.0163 (7)	0.0213 (8)	−0.0018 (5)	−0.0019 (6)	0.0013 (6)
C5	0.0198 (7)	0.0131 (7)	0.0315 (9)	−0.0005 (5)	−0.0002 (6)	−0.0060 (6)
C6	0.0272 (8)	0.0199 (7)	0.0304 (8)	−0.0015 (6)	−0.0044 (6)	−0.0107 (6)

O1—C1	1.4153 (19)	O1—H1A	0.820
O2—C2	1.4017 (16)	O2—H2A	0.820
O3—C3	1.419 (2)	O3—H3A	0.820
O4—C4	1.4395 (16)	O4—H4A	0.820
O5—C5	1.4305 (17)	O5—H5A	0.820
O6—C2	1.423 (2)	C1—H1C	0.970
O6—C6	1.4298 (19)	C1—H1B	0.970
C1—C2	1.520 (2)	C3—H3B	0.980
C2—C3	1.5304 (19)	C4—H4B	0.980
C3—C4	1.521 (2)	C5—H5B	0.980
C4—C5	1.517 (2)	C6—H6A	0.970
C5—C6	1.5075 (19)	C6—H6B	0.970
C2—O6—C6	113.25 (10)	C4—O4—H4A	109.467
O1—C1—C2	111.97 (14)	C5—O5—H5A	109.473
O2—C2—O6	111.23 (13)	O1—C1—H1C	109.215
O2—C2—C1	112.44 (10)	O1—C1—H1B	109.220
O2—C2—C3	107.69 (10)	C2—C1—H1C	109.218
O6—C2—C1	105.55 (11)	C2—C1—H1B	109.221
O6—C2—C3	109.06 (10)	H1C—C1—H1B	107.907
C1—C2—C3	110.86 (13)	O3—C3—H3B	109.026
O3—C3—C2	109.62 (10)	C2—C3—H3B	109.028
O3—C3—C4	110.08 (11)	C4—C3—H3B	109.024
C2—C3—C4	110.04 (13)	O4—C4—H4B	109.255
O4—C4—C3	110.05 (13)	C3—C4—H4B	109.253
O4—C4—C5	109.74 (10)	C5—C4—H4B	109.254
C3—C4—C5	109.27 (11)	O5—C5—H5B	109.808
O5—C5—C4	110.97 (14)	C4—C5—H5B	109.810
O5—C5—C6	107.71 (11)	C6—C5—H5B	109.807
C4—C5—C6	108.69 (11)	O6—C6—H6A	109.512
O6—C6—C5	110.67 (14)	O6—C6—H6B	109.511
C1—O1—H1A	109.469	C5—C6—H6A	109.511
C2—O2—H2A	109.478	C5—C6—H6B	109.513
C3—O3—H3A	109.476	H6A—C6—H6B	108.082
C2—O6—C6—C5	−61.73 (13)	C1—C2—C3—C4	−172.62 (10)
C6—O6—C2—O2	−58.74 (12)	O3—C3—C4—O4	−62.10 (13)
C6—O6—C2—C1	179.03 (9)	O3—C3—C4—C5	177.33 (9)
C6—O6—C2—C3	59.88 (13)	C2—C3—C4—O4	176.97 (10)
O1—C1—C2—O2	−68.49 (15)	C2—C3—C4—C5	56.41 (12)
O1—C1—C2—O6	52.95 (13)	O4—C4—C5—O5	−58.98 (13)
O1—C1—C2—C3	170.90 (9)	O4—C4—C5—C6	−177.25 (10)
O2—C2—C3—O3	−57.21 (15)	C3—C4—C5—O5	61.77 (12)
O2—C2—C3—C4	63.99 (14)	C3—C4—C5—C6	−56.50 (14)
O6—C2—C3—O3	−178.02 (10)	O5—C5—C6—O6	−61.97 (15)
O6—C2—C3—C4	−56.82 (13)	C4—C5—C6—O6	58.34 (14)
C1—C2—C3—O3	66.18 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3i	0.82	2.28	2.9202 (14)	135
O2—H2A···O1	0.82	2.60	2.9721 (14)	110
O2—H2A···O1ii	0.82	1.93	2.7224 (13)	161
O3—H3A···O4iii	0.82	1.96	2.7831 (18)	177
O4—H4A···O5iv	0.82	2.01	2.7893 (13)	158
O5—H5A···O4v	0.82	2.05	2.8431 (12)	163

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1AO3i	0.82	2.28	2.9202(14)	135
O2H2AO1ii	0.82	1.93	2.7224(13)	161
O3H3AO4iii	0.82	1.96	2.7831(18)	177
O4H4AO5iv	0.82	2.01	2.7893(13)	158
O5H5AO4v	0.82	2.05	2.8431(12)	163

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