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The structure of the the title compound, C7H14O6, a natural myo-inositol derivative, has been determined. Bond distances, bond lengths and dihedral angles are similar to those of myo-inositol.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037019/av3033sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037019/av3033Isup2.hkl
Contains datablock I

CCDC reference: 636128

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.085
  • Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level B ABSMU01_ALERT_1_B The ratio of given/expected absorption coefficient lies outside the range 0.95 <> 1.05 Calculated value of mu = 0.134 Value of mu given = 0.126 PLAT411_ALERT_2_B Short Inter H...H Contact H4A .. H6A .. 2.09 Ang.
Alert level C PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.19 Ratio PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C7 H14 O6
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 27.49 From the CIF: _reflns_number_total 1151 Count of symmetry unique reflns 1156 Completeness (_total/calc) 99.57% 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 C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

L-(+)-bornesito top
Crystal data top
C7H14O6Dx = 1.521 Mg m3
Mr = 194.19Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 5715 reflections
Hall symbol: P 2ac 2abθ = 3–27°
a = 6.5756 (4) ŵ = 0.13 mm1
b = 11.0565 (7) ÅT = 150 K
c = 11.6622 (9) ÅPlate, colourless
V = 847.88 (10) Å30.48 × 0.44 × 0.23 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
974 reflections with I > 2σ(I)
Graphite 002 monochromatorRint = 0.035
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(Otwinowski & Minor, 1997)
h = 88
Tmin = 0.926, Tmax = 0.972k = 1414
5715 measured reflectionsl = 1515
1151 independent reflections
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full 1/[σ2(Fo2) + (0.0543P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.034(Δ/σ)max < 0.001
wR(F2) = 0.085Δρmax = 0.19 e Å3
S = 1.05Δρmin = 0.20 e Å3
1151 reflectionsExtinction correction: SHELXL97
140 parametersExtinction coefficient: 0.36E-01
0 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6279 (2)0.17007 (13)0.20084 (13)0.0265 (4)
O20.3604 (2)0.33666 (12)0.30769 (13)0.0241 (4)
O30.0598 (2)0.28557 (12)0.30820 (14)0.0266 (4)
O40.0579 (2)0.09871 (13)0.47427 (15)0.0256 (4)
O50.3358 (2)0.01213 (13)0.54607 (13)0.0256 (4)
O60.6278 (2)0.00787 (12)0.36698 (13)0.0224 (3)
C10.4383 (3)0.13218 (17)0.24860 (17)0.0188 (4)
C20.2804 (3)0.23312 (16)0.24943 (18)0.0201 (4)
C30.0859 (3)0.18911 (16)0.30673 (18)0.0202 (4)
C40.1276 (3)0.14502 (17)0.42785 (17)0.0193 (4)
C50.2921 (3)0.04731 (17)0.43126 (17)0.0188 (4)
C60.4846 (3)0.08912 (17)0.36957 (17)0.0175 (4)
C70.6247 (3)0.1929 (2)0.08045 (18)0.0285 (5)
H10.38460.06270.20280.023*
H20.361 (5)0.393 (2)0.257 (3)0.048 (8)*
H30.186 (4)0.256 (2)0.280 (3)0.049 (8)*
H40.066 (5)0.124 (3)0.545 (3)0.067 (10)*
H50.386 (5)0.078 (3)0.579 (3)0.057 (9)*
H60.741 (5)0.025 (3)0.397 (3)0.049 (8)*
H2A0.24880.25610.16840.024*
H3A0.02920.12050.26090.024*
H4A0.17300.21520.47550.023*
H5A0.23880.02520.38980.023*
H6A0.54530.15780.41360.021*
H7A0.56670.27310.06620.043*
H7B0.76370.18990.05030.043*
H7C0.54160.13140.04220.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0200 (7)0.0420 (8)0.0175 (7)0.0055 (6)0.0026 (6)0.0005 (7)
O20.0314 (8)0.0194 (6)0.0216 (8)0.0047 (6)0.0047 (7)0.0014 (6)
O30.0213 (7)0.0268 (7)0.0319 (9)0.0064 (7)0.0036 (6)0.0045 (7)
O40.0186 (6)0.0354 (8)0.0227 (8)0.0074 (7)0.0049 (6)0.0051 (7)
O50.0329 (8)0.0258 (7)0.0182 (8)0.0035 (7)0.0005 (6)0.0035 (6)
O60.0194 (7)0.0213 (6)0.0265 (8)0.0037 (6)0.0034 (6)0.0050 (6)
C10.0158 (9)0.0238 (9)0.0167 (10)0.0022 (8)0.0002 (8)0.0004 (8)
C20.0236 (10)0.0202 (9)0.0164 (10)0.0024 (8)0.0029 (8)0.0025 (8)
C30.0189 (9)0.0210 (8)0.0206 (10)0.0021 (8)0.0012 (8)0.0043 (8)
C40.0170 (9)0.0212 (9)0.0199 (10)0.0031 (8)0.0022 (8)0.0040 (8)
C50.0212 (9)0.0169 (8)0.0182 (10)0.0013 (8)0.0003 (8)0.0001 (7)
C60.0188 (9)0.0169 (8)0.0167 (10)0.0019 (8)0.0006 (7)0.0019 (7)
C70.0303 (10)0.0386 (11)0.0165 (10)0.0046 (10)0.0039 (9)0.0007 (9)
Geometric parameters (Å, º) top
O6—C61.427 (2)C5—H5A1.000
O6—H60.90 (3)C2—C31.523 (3)
O1—C71.427 (3)C2—C11.524 (3)
O1—C11.428 (2)C2—H2A1.000
O4—C41.429 (2)C1—C61.520 (3)
O4—H40.87 (4)C1—H11.000
O2—C21.431 (2)C4—C31.519 (3)
O2—H20.86 (3)C4—H4A1.000
O3—C31.434 (2)C3—H3A1.000
O3—H30.95 (3)C6—H6A1.000
O5—C51.424 (2)C7—H7A0.980
O5—H50.89 (3)C7—H7B0.980
C5—C61.528 (3)C7—H7C0.980
C5—C41.529 (3)
C6—O6—H6103.2 (18)O4—C4—C3108.26 (15)
C7—O1—C1115.02 (16)O4—C4—C5109.92 (15)
C4—O4—H4107 (2)C3—C4—C5112.23 (15)
C2—O2—H2104.8 (19)O4—C4—H4A108.80
C3—O3—H3108.7 (16)C3—C4—H4A108.80
C5—O5—H5105 (2)C5—C4—H4A108.80
O5—C5—C6111.00 (16)O3—C3—C4110.37 (16)
O5—C5—C4111.12 (16)O3—C3—C2109.20 (14)
C6—C5—C4111.11 (15)C4—C3—C2111.04 (15)
O5—C5—H5A107.80O3—C3—H3A108.70
C6—C5—H5A107.80C4—C3—H3A108.70
C4—C5—H5A107.80C2—C3—H3A108.70
O2—C2—C3110.84 (16)O6—C6—C1110.36 (15)
O2—C2—C1109.78 (16)O6—C6—C5109.21 (15)
C3—C2—C1109.93 (15)C1—C6—C5111.47 (15)
O2—C2—H2A108.70O6—C6—H6A108.60
C3—C2—H2A108.70C1—C6—H6A108.60
C1—C2—H2A108.70C5—C6—H6A108.60
O1—C1—C6106.20 (14)O1—C7—H7A109.50
O1—C1—C2112.47 (15)O1—C7—H7B109.50
C6—C1—C2111.10 (16)H7A—C7—H7B109.50
O1—C1—H1109.00O1—C7—H7C109.50
C6—C1—H1109.00H7A—C7—H7C109.50
C2—C1—H1109.00H7B—C7—H7C109.50
C7—O1—C1—C6168.90 (16)C5—C4—C3—C255.22 (19)
C7—O1—C1—C269.4 (2)O2—C2—C3—O357.7 (2)
O2—C2—C1—O154.9 (2)C1—C2—C3—O3179.21 (15)
C3—C2—C1—O1177.12 (15)O2—C2—C3—C464.26 (19)
O2—C2—C1—C664.0 (2)C1—C2—C3—C457.3 (2)
C3—C2—C1—C658.2 (2)O1—C1—C6—O659.23 (18)
O5—C5—C4—O462.5 (2)C2—C1—C6—O6178.17 (14)
C6—C5—C4—O4173.35 (16)O1—C1—C6—C5179.23 (15)
O5—C5—C4—C3176.94 (16)C2—C1—C6—C556.6 (2)
C6—C5—C4—C352.8 (2)O5—C5—C6—O660.3 (2)
O4—C4—C3—O362.05 (18)C4—C5—C6—O6175.49 (14)
C5—C4—C3—O3176.46 (14)O5—C5—C6—C1177.48 (15)
O4—C4—C3—C2176.71 (14)C4—C5—C6—C153.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O6i0.86 (3)1.82 (3)2.667 (3)170 (3)
O3—H3···O1ii0.95 (3)1.80 (3)2.723 (3)162 (3)
O4—H4···O2iii0.87 (3)1.84 (3)2.695 (3)167 (3)
O5—H5···O3iv0.89 (3)2.03 (3)2.892 (3)163 (3)
O6—H6···O4v0.90 (3)1.80 (3)2.688 (3)171 (3)
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x1, y, z; (iii) x1/2, y1/2, z+1; (iv) x+1/2, y1/2, z+1; (v) x+1, y, z.
 

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