Methyl β-D-fructopyran­oside

In methyl β-D-fructopyran­oside, C₇H₁₄O₆, the thermodynamically most stable methyl glycoside of the ketose D-fructose, the pyran­ose ring is close to being an ideal ²C₅ chair. The compound forms bilayers involving a complex hydrogen-bonding pattern of five independent hydrogen bonds. Graph-set analysis was applied to distinguish the hydrogen-bond patterns at unary and higher level graph sets.

Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: PLATON (Spek, 2009).

Methyl β-D-fructopyranoside

Crystal data

C7H14O6	F(000) = 416
Mr = 194.18	Dx = 1.488 (1) Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 2304 reflections
a = 14.9990 (8) Å	θ = 4.3–26.3°
b = 5.4114 (3) Å	µ = 0.13 mm^−1
c = 10.8287 (6) Å	T = 200 K
β = 99.477 (5)°	Platelet, colourless
V = 866.92 (8) Å^3	0.51 × 0.49 × 0.15 mm
Z = 4

Data collection

Oxford XCalibur CCD diffractometer	914 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 26.3°, θmin = 4.3°
CCD; rotation images scans	h = −18→18
2704 measured reflections	k = −6→6
976 independent reflections	l = −9→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0603P)^2 + 0.1474P] where P = (Fo^2 + 2Fc^2)/3
976 reflections	(Δ/σ)max < 0.001
123 parameters	Δρmax = 0.23 e Å^−3
1 restraint	Δρmin = −0.21 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.22979 (10)	0.7882 (3)	0.79565 (17)	0.0306 (4)
H81	0.2648	0.9100	0.7991	0.046*
O2	0.28321 (10)	0.2751 (3)	0.69063 (14)	0.0245 (4)
O3	0.35951 (10)	0.1116 (4)	0.92245 (13)	0.0260 (4)
H83	0.3920	0.0761	0.9909	0.039*
O4	0.53424 (10)	0.0164 (3)	0.85266 (14)	0.0265 (4)
H84	0.5330	−0.1295	0.8260	0.040*
O5	0.56719 (10)	0.5123 (3)	0.79179 (16)	0.0284 (4)
H85	0.6182	0.4456	0.8104	0.043*
O6	0.37792 (9)	0.6212 (3)	0.71050 (12)	0.0216 (3)
C1	0.27679 (15)	0.5832 (5)	0.8571 (2)	0.0265 (5)
H11	0.2324	0.4679	0.8838	0.032*
H12	0.3167	0.6424	0.9333	0.032*
C2	0.33371 (13)	0.4431 (4)	0.77547 (18)	0.0187 (5)
C3	0.40532 (13)	0.2835 (4)	0.85701 (18)	0.0187 (4)
H3	0.4433	0.3927	0.9192	0.022*
C4	0.46606 (13)	0.1586 (4)	0.77620 (18)	0.0198 (5)
H4	0.4288	0.0475	0.7142	0.024*
C5	0.50970 (14)	0.3580 (4)	0.7068 (2)	0.0229 (5)
H5	0.5459	0.2781	0.6481	0.027*
C6	0.43646 (15)	0.5152 (5)	0.63279 (19)	0.0250 (5)
H61	0.4647	0.6494	0.5906	0.030*
H62	0.4003	0.4125	0.5673	0.030*
C7	0.20559 (15)	0.3736 (6)	0.6120 (2)	0.0344 (6)
H71	0.1569	0.3976	0.6611	0.052*
H72	0.1855	0.2582	0.5433	0.052*
H73	0.2210	0.5325	0.5777	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0189 (8)	0.0189 (8)	0.0548 (10)	0.0011 (7)	0.0085 (7)	−0.0009 (8)
O2	0.0192 (7)	0.0231 (8)	0.0288 (7)	−0.0011 (7)	−0.0026 (5)	−0.0054 (7)
O3	0.0228 (7)	0.0299 (9)	0.0245 (7)	−0.0060 (7)	0.0017 (5)	0.0077 (7)
O4	0.0269 (8)	0.0187 (9)	0.0310 (7)	0.0065 (7)	−0.0041 (6)	−0.0026 (6)
O5	0.0155 (7)	0.0217 (9)	0.0474 (9)	0.0013 (7)	0.0036 (6)	−0.0026 (7)
O6	0.0199 (7)	0.0184 (7)	0.0279 (7)	0.0014 (7)	0.0082 (5)	0.0015 (7)
C1	0.0224 (10)	0.0252 (12)	0.0330 (10)	0.0028 (10)	0.0078 (8)	−0.0020 (10)
C2	0.0166 (9)	0.0168 (11)	0.0224 (9)	−0.0020 (9)	0.0019 (7)	−0.0006 (8)
C3	0.0160 (9)	0.0171 (10)	0.0231 (9)	−0.0013 (9)	0.0035 (7)	−0.0005 (8)
C4	0.0174 (9)	0.0177 (11)	0.0235 (9)	0.0030 (9)	0.0005 (7)	−0.0021 (8)
C5	0.0205 (10)	0.0208 (12)	0.0293 (10)	0.0015 (9)	0.0095 (8)	−0.0020 (9)
C6	0.0247 (10)	0.0252 (13)	0.0265 (10)	0.0038 (10)	0.0087 (8)	0.0045 (9)
C7	0.0219 (12)	0.0422 (16)	0.0351 (12)	0.0026 (11)	−0.0067 (9)	−0.0046 (11)

Geometric parameters (Å, º)

O1—C1	1.420 (3)	C1—H12	0.9900
O1—H81	0.8400	C2—C3	1.538 (3)
O2—C2	1.420 (2)	C3—C4	1.522 (3)
O2—C7	1.427 (3)	C3—H3	1.0000
O3—C3	1.414 (3)	C4—C5	1.523 (3)
O3—H83	0.8400	C4—H4	1.0000
O4—C4	1.430 (2)	C5—C6	1.511 (3)
O4—H84	0.8400	C5—H5	1.0000
O5—C5	1.424 (3)	C6—H61	0.9900
O5—H85	0.8400	C6—H62	0.9900
O6—C2	1.420 (3)	C7—H71	0.9800
O6—C6	1.432 (3)	C7—H72	0.9800
C1—C2	1.527 (3)	C7—H73	0.9800
C1—H11	0.9900
C1—O1—H81	109.5	O4—C4—C3	110.18 (15)
C2—O2—C7	116.27 (18)	O4—C4—C5	110.03 (16)
C3—O3—H83	109.5	C3—C4—C5	108.41 (18)
C4—O4—H84	109.5	O4—C4—H4	109.4
C5—O5—H85	109.5	C3—C4—H4	109.4
C2—O6—C6	113.64 (17)	C5—C4—H4	109.4
O1—C1—C2	113.48 (17)	O5—C5—C6	108.81 (18)
O1—C1—H11	108.9	O5—C5—C4	111.10 (17)
C2—C1—H11	108.9	C6—C5—C4	109.06 (17)
O1—C1—H12	108.9	O5—C5—H5	109.3
C2—C1—H12	108.9	C6—C5—H5	109.3
H11—C1—H12	107.7	C4—C5—H5	109.3
O2—C2—O6	110.91 (15)	O6—C6—C5	112.13 (16)
O2—C2—C1	113.75 (16)	O6—C6—H61	109.2
O6—C2—C1	107.53 (18)	C5—C6—H61	109.2
O2—C2—C3	105.04 (17)	O6—C6—H62	109.2
O6—C2—C3	109.06 (16)	C5—C6—H62	109.2
C1—C2—C3	110.51 (16)	H61—C6—H62	107.9
O3—C3—C4	112.47 (18)	O2—C7—H71	109.5
O3—C3—C2	107.82 (16)	O2—C7—H72	109.5
C4—C3—C2	110.29 (15)	H71—C7—H72	109.5
O3—C3—H3	108.7	O2—C7—H73	109.5
C4—C3—H3	108.7	H71—C7—H73	109.5
C2—C3—H3	108.7	H72—C7—H73	109.5
C7—O2—C2—O6	−68.6 (2)	O6—C2—C3—C4	−58.0 (2)
C7—O2—C2—C1	52.7 (2)	C1—C2—C3—C4	−176.03 (18)
C7—O2—C2—C3	173.69 (17)	O3—C3—C4—O4	−61.4 (2)
C6—O6—C2—O2	−57.0 (2)	C2—C3—C4—O4	178.24 (16)
C6—O6—C2—C1	178.08 (16)	O3—C3—C4—C5	178.19 (15)
C6—O6—C2—C3	58.22 (19)	C2—C3—C4—C5	57.8 (2)
O1—C1—C2—O2	−80.8 (2)	O4—C4—C5—O5	−56.7 (2)
O1—C1—C2—O6	42.4 (2)	C3—C4—C5—O5	63.9 (2)
O1—C1—C2—C3	161.32 (18)	O4—C4—C5—C6	−176.63 (16)
O2—C2—C3—O3	−62.26 (19)	C3—C4—C5—C6	−56.1 (2)
O6—C2—C3—O3	178.81 (16)	C2—O6—C6—C5	−58.9 (2)
C1—C2—C3—O3	60.8 (2)	O5—C5—C6—O6	−64.9 (2)
O2—C2—C3—C4	60.9 (2)	C4—C5—C6—O6	56.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H81···O2^i	0.84	2.34	3.029 (2)	140
O1—H81···O3^i	0.84	2.09	2.802 (2)	142
O3—H83···O4^ii	0.84	1.89	2.731 (2)	177
O4—H84···O5^iii	0.84	2.05	2.868 (2)	163
O5—H85···O1^iv	0.84	1.91	2.718 (2)	162
C4—H4···O6^iii	1.00	2.43	3.226 (2)	136

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