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
CCDC reference: 636128
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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.
Crystal data top
C7H14O6 | Dx = 1.521 Mg m−3 |
Mr = 194.19 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 5715 reflections |
Hall symbol: P 2ac 2ab | θ = 3–27° |
a = 6.5756 (4) Å | µ = 0.13 mm−1 |
b = 11.0565 (7) Å | T = 150 K |
c = 11.6622 (9) Å | Plate, colourless |
V = 847.88 (10) Å3 | 0.48 × 0.44 × 0.23 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 974 reflections with I > 2σ(I) |
Graphite 002 monochromator | Rint = 0.035 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (Otwinowski & Minor, 1997) | h = −8→8 |
Tmin = 0.926, Tmax = 0.972 | k = −14→14 |
5715 measured reflections | l = −15→15 |
1151 independent reflections | |
Refinement top
Refinement on F2 | H 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) = 0.085 | Δρmax = 0.19 e Å−3 |
S = 1.05 | Δρmin = −0.20 e Å−3 |
1151 reflections | Extinction correction: SHELXL97 |
140 parameters | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.6279 (2) | −0.17007 (13) | 0.20084 (13) | 0.0265 (4) | |
O2 | 0.3604 (2) | −0.33666 (12) | 0.30769 (13) | 0.0241 (4) | |
O3 | −0.0598 (2) | −0.28557 (12) | 0.30820 (14) | 0.0266 (4) | |
O4 | −0.0579 (2) | −0.09871 (13) | 0.47427 (15) | 0.0256 (4) | |
O5 | 0.3358 (2) | −0.01213 (13) | 0.54607 (13) | 0.0256 (4) | |
O6 | 0.6278 (2) | 0.00787 (12) | 0.36698 (13) | 0.0224 (3) | |
C1 | 0.4383 (3) | −0.13218 (17) | 0.24860 (17) | 0.0188 (4) | |
C2 | 0.2804 (3) | −0.23312 (16) | 0.24943 (18) | 0.0201 (4) | |
C3 | 0.0859 (3) | −0.18911 (16) | 0.30673 (18) | 0.0202 (4) | |
C4 | 0.1276 (3) | −0.14502 (17) | 0.42785 (17) | 0.0193 (4) | |
C5 | 0.2921 (3) | −0.04731 (17) | 0.43126 (17) | 0.0188 (4) | |
C6 | 0.4846 (3) | −0.08912 (17) | 0.36957 (17) | 0.0175 (4) | |
C7 | 0.6247 (3) | −0.1929 (2) | 0.08045 (18) | 0.0285 (5) | |
H1 | 0.3846 | −0.0627 | 0.2028 | 0.023* | |
H2 | 0.361 (5) | −0.393 (2) | 0.257 (3) | 0.048 (8)* | |
H3 | −0.186 (4) | −0.256 (2) | 0.280 (3) | 0.049 (8)* | |
H4 | −0.066 (5) | −0.124 (3) | 0.545 (3) | 0.067 (10)* | |
H5 | 0.386 (5) | −0.078 (3) | 0.579 (3) | 0.057 (9)* | |
H6 | 0.741 (5) | −0.025 (3) | 0.397 (3) | 0.049 (8)* | |
H2A | 0.2488 | −0.2561 | 0.1684 | 0.024* | |
H3A | 0.0292 | −0.1205 | 0.2609 | 0.024* | |
H4A | 0.1730 | −0.2152 | 0.4755 | 0.023* | |
H5A | 0.2388 | 0.0252 | 0.3898 | 0.023* | |
H6A | 0.5453 | −0.1578 | 0.4136 | 0.021* | |
H7A | 0.5667 | −0.2731 | 0.0662 | 0.043* | |
H7B | 0.7637 | −0.1899 | 0.0503 | 0.043* | |
H7C | 0.5416 | −0.1314 | 0.0422 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0200 (7) | 0.0420 (8) | 0.0175 (7) | 0.0055 (6) | 0.0026 (6) | −0.0005 (7) |
O2 | 0.0314 (8) | 0.0194 (6) | 0.0216 (8) | 0.0047 (6) | −0.0047 (7) | −0.0014 (6) |
O3 | 0.0213 (7) | 0.0268 (7) | 0.0319 (9) | −0.0064 (7) | −0.0036 (6) | 0.0045 (7) |
O4 | 0.0186 (6) | 0.0354 (8) | 0.0227 (8) | 0.0074 (7) | 0.0049 (6) | 0.0051 (7) |
O5 | 0.0329 (8) | 0.0258 (7) | 0.0182 (8) | 0.0035 (7) | −0.0005 (6) | −0.0035 (6) |
O6 | 0.0194 (7) | 0.0213 (6) | 0.0265 (8) | −0.0037 (6) | −0.0034 (6) | 0.0050 (6) |
C1 | 0.0158 (9) | 0.0238 (9) | 0.0167 (10) | 0.0022 (8) | 0.0002 (8) | 0.0004 (8) |
C2 | 0.0236 (10) | 0.0202 (9) | 0.0164 (10) | 0.0024 (8) | −0.0029 (8) | 0.0025 (8) |
C3 | 0.0189 (9) | 0.0210 (8) | 0.0206 (10) | −0.0021 (8) | −0.0012 (8) | 0.0043 (8) |
C4 | 0.0170 (9) | 0.0212 (9) | 0.0199 (10) | 0.0031 (8) | 0.0022 (8) | 0.0040 (8) |
C5 | 0.0212 (9) | 0.0169 (8) | 0.0182 (10) | 0.0013 (8) | 0.0003 (8) | 0.0001 (7) |
C6 | 0.0188 (9) | 0.0169 (8) | 0.0167 (10) | −0.0019 (8) | −0.0006 (7) | 0.0019 (7) |
C7 | 0.0303 (10) | 0.0386 (11) | 0.0165 (10) | 0.0046 (10) | 0.0039 (9) | 0.0007 (9) |
Geometric parameters (Å, º) top
O6—C6 | 1.427 (2) | C5—H5A | 1.000 |
O6—H6 | 0.90 (3) | C2—C3 | 1.523 (3) |
O1—C7 | 1.427 (3) | C2—C1 | 1.524 (3) |
O1—C1 | 1.428 (2) | C2—H2A | 1.000 |
O4—C4 | 1.429 (2) | C1—C6 | 1.520 (3) |
O4—H4 | 0.87 (4) | C1—H1 | 1.000 |
O2—C2 | 1.431 (2) | C4—C3 | 1.519 (3) |
O2—H2 | 0.86 (3) | C4—H4A | 1.000 |
O3—C3 | 1.434 (2) | C3—H3A | 1.000 |
O3—H3 | 0.95 (3) | C6—H6A | 1.000 |
O5—C5 | 1.424 (2) | C7—H7A | 0.980 |
O5—H5 | 0.89 (3) | C7—H7B | 0.980 |
C5—C6 | 1.528 (3) | C7—H7C | 0.980 |
C5—C4 | 1.529 (3) | | |
| | | |
C6—O6—H6 | 103.2 (18) | O4—C4—C3 | 108.26 (15) |
C7—O1—C1 | 115.02 (16) | O4—C4—C5 | 109.92 (15) |
C4—O4—H4 | 107 (2) | C3—C4—C5 | 112.23 (15) |
C2—O2—H2 | 104.8 (19) | O4—C4—H4A | 108.80 |
C3—O3—H3 | 108.7 (16) | C3—C4—H4A | 108.80 |
C5—O5—H5 | 105 (2) | C5—C4—H4A | 108.80 |
O5—C5—C6 | 111.00 (16) | O3—C3—C4 | 110.37 (16) |
O5—C5—C4 | 111.12 (16) | O3—C3—C2 | 109.20 (14) |
C6—C5—C4 | 111.11 (15) | C4—C3—C2 | 111.04 (15) |
O5—C5—H5A | 107.80 | O3—C3—H3A | 108.70 |
C6—C5—H5A | 107.80 | C4—C3—H3A | 108.70 |
C4—C5—H5A | 107.80 | C2—C3—H3A | 108.70 |
O2—C2—C3 | 110.84 (16) | O6—C6—C1 | 110.36 (15) |
O2—C2—C1 | 109.78 (16) | O6—C6—C5 | 109.21 (15) |
C3—C2—C1 | 109.93 (15) | C1—C6—C5 | 111.47 (15) |
O2—C2—H2A | 108.70 | O6—C6—H6A | 108.60 |
C3—C2—H2A | 108.70 | C1—C6—H6A | 108.60 |
C1—C2—H2A | 108.70 | C5—C6—H6A | 108.60 |
O1—C1—C6 | 106.20 (14) | O1—C7—H7A | 109.50 |
O1—C1—C2 | 112.47 (15) | O1—C7—H7B | 109.50 |
C6—C1—C2 | 111.10 (16) | H7A—C7—H7B | 109.50 |
O1—C1—H1 | 109.00 | O1—C7—H7C | 109.50 |
C6—C1—H1 | 109.00 | H7A—C7—H7C | 109.50 |
C2—C1—H1 | 109.00 | H7B—C7—H7C | 109.50 |
| | | |
C7—O1—C1—C6 | −168.90 (16) | C5—C4—C3—C2 | 55.22 (19) |
C7—O1—C1—C2 | 69.4 (2) | O2—C2—C3—O3 | −57.7 (2) |
O2—C2—C1—O1 | 54.9 (2) | C1—C2—C3—O3 | −179.21 (15) |
C3—C2—C1—O1 | 177.12 (15) | O2—C2—C3—C4 | 64.26 (19) |
O2—C2—C1—C6 | −64.0 (2) | C1—C2—C3—C4 | −57.3 (2) |
C3—C2—C1—C6 | 58.2 (2) | O1—C1—C6—O6 | 59.23 (18) |
O5—C5—C4—O4 | 62.5 (2) | C2—C1—C6—O6 | −178.17 (14) |
C6—C5—C4—O4 | −173.35 (16) | O1—C1—C6—C5 | −179.23 (15) |
O5—C5—C4—C3 | −176.94 (16) | C2—C1—C6—C5 | −56.6 (2) |
C6—C5—C4—C3 | −52.8 (2) | O5—C5—C6—O6 | −60.3 (2) |
O4—C4—C3—O3 | −62.05 (18) | C4—C5—C6—O6 | 175.49 (14) |
C5—C4—C3—O3 | 176.46 (14) | O5—C5—C6—C1 | 177.48 (15) |
O4—C4—C3—C2 | 176.71 (14) | C4—C5—C6—C1 | 53.3 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O6i | 0.86 (3) | 1.82 (3) | 2.667 (3) | 170 (3) |
O3—H3···O1ii | 0.95 (3) | 1.80 (3) | 2.723 (3) | 162 (3) |
O4—H4···O2iii | 0.87 (3) | 1.84 (3) | 2.695 (3) | 167 (3) |
O5—H5···O3iv | 0.89 (3) | 2.03 (3) | 2.892 (3) | 163 (3) |
O6—H6···O4v | 0.90 (3) | 1.80 (3) | 2.688 (3) | 171 (3) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, y, z; (iii) x−1/2, −y−1/2, −z+1; (iv) x+1/2, −y−1/2, −z+1; (v) x+1, y, z. |