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The title compound C7H10O5, crystallizes in the space group P31 as individual mol­ecules on a three old screw axis, and is stabilized by strong intermolecular hydrogen bonds between the methyl­ene alcohol [O—H...O 1.75 (5) Å] and the two secondary alcohol moieties [O—H...O 1.81 (3) and 1.91 (3) Å] .

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017975/cv6218sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017975/cv6218Isup2.hkl
Contains datablock I

CCDC reference: 225785

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.035
  • wR factor = 0.067
  • Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) . 3.24 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang.. 5 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ...... 3
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 28.27 From the CIF: _reflns_number_total 1009 Count of symmetry unique reflns 1008 Completeness (_total/calc) 100.10% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus and XPREP (Bruker, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia,1999).

(I) top
Crystal data top
C7H10O5Dx = 1.414 Mg m3
Mr = 174.15Mo Kα radiation, λ = 0.71069 Å
Trigonal, P31Cell parameters from 293 reflections
Hall symbol: P 31θ = 4–21°
a = 11.532 (5) ŵ = 0.12 mm1
c = 5.328 (5) ÅT = 293 K
V = 613.6 (7) Å3Cuboid, colorless
Z = 30.26 × 0.12 × 0.1 mm
F(000) = 276
Data collection top
Bruker SMART 1K CCD
diffractometer
586 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.071
Graphite monochromatorθmax = 28.3°, θmin = 2.0°
ω scansh = 1515
4357 measured reflectionsk = 1513
1009 independent reflectionsl = 57
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H atoms treated by a mixture of independent and constrained refinement
S = 0.90 w = 1/[σ2(Fo2) + (0.027P)2]
where P = (Fo2 + 2Fc2)/3
1009 reflections(Δ/σ)max < 0.001
121 parametersΔρmax = 0.12 e Å3
1 restraintΔρmin = 0.18 e Å3
Special details top

Experimental. The intensity data were collected on a Siemens SMART CCD 1 K diffractometer using an exposure time of 10 s/frame. A total of 1315 frames were collected with a frame width of 0.3° covering up to θ = 28.27° with 99.9% completeness accomplished. The first 50 frames were recollected at the end of the data collection to check for decay; none was found.

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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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
O11.0050 (2)0.45504 (18)0.1634 (3)0.0387 (6)
O30.9692 (2)0.1223 (2)0.6143 (3)0.0386 (5)
O41.0261 (2)0.1584 (2)0.1071 (4)0.0426 (6)
O51.2491 (2)0.5562 (3)0.4200 (5)0.0554 (7)
C40.9689 (3)0.3293 (3)0.5463 (5)0.0335 (7)
H41.02940.3560.69090.04*
C11.0420 (3)0.3670 (3)0.2913 (5)0.0286 (7)
C20.9579 (3)0.2202 (3)0.2074 (5)0.0309 (7)
H20.88550.20860.0950.037*
C30.9058 (3)0.1804 (3)0.4784 (5)0.0312 (7)
H30.80790.13050.49120.037*
O20.8645 (3)0.5322 (3)0.2175 (5)0.0831 (9)
C60.9122 (3)0.4682 (3)0.2979 (6)0.0458 (8)
C71.1914 (3)0.4313 (3)0.2899 (6)0.0465 (9)
H7A1.21780.37270.37060.056*
H7B1.22370.4460.11820.056*
C50.8821 (4)0.3942 (4)0.5409 (6)0.0508 (9)
H5A0.7880.32670.55030.061*
H5B0.90350.45530.68110.061*
H041.006 (3)0.146 (3)0.047 (7)0.060 (12)*
H030.925 (5)0.032 (4)0.567 (8)0.103 (16)*
H051.255 (5)0.621 (6)0.306 (9)0.120 (19)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0576 (14)0.0382 (12)0.0311 (12)0.0320 (11)0.0000 (11)0.0052 (9)
O30.0620 (14)0.0333 (13)0.0262 (11)0.0281 (12)0.0045 (10)0.0015 (10)
O40.0682 (16)0.0570 (15)0.0232 (13)0.0468 (12)0.0048 (11)0.0068 (11)
O50.0433 (15)0.0375 (14)0.0691 (19)0.0079 (11)0.0151 (12)0.0012 (13)
C40.0487 (19)0.0344 (17)0.0236 (16)0.0254 (16)0.0014 (14)0.0025 (14)
C10.0366 (18)0.0300 (16)0.0257 (17)0.0214 (15)0.0012 (13)0.0032 (13)
C20.0334 (17)0.0370 (17)0.0266 (16)0.0207 (15)0.0064 (13)0.0034 (14)
C30.0339 (17)0.0306 (16)0.0306 (17)0.0172 (14)0.0006 (13)0.0005 (14)
O20.125 (3)0.107 (2)0.075 (2)0.102 (2)0.0075 (18)0.0076 (17)
C60.063 (2)0.046 (2)0.046 (2)0.040 (2)0.0069 (18)0.0020 (17)
C70.040 (2)0.047 (2)0.051 (2)0.0202 (17)0.0037 (16)0.0027 (18)
C50.067 (2)0.050 (2)0.051 (2)0.040 (2)0.0137 (19)0.0034 (17)
Geometric parameters (Å, º) top
O1—C61.358 (4)C1—C71.497 (4)
O1—C11.453 (3)C1—C21.538 (4)
O3—C31.413 (3)C2—C31.543 (4)
O3—H030.93 (4)C2—H20.98
O4—C21.404 (3)C3—H30.98
O4—H040.85 (4)O2—C61.198 (4)
O5—C71.428 (4)C6—C51.493 (5)
O5—H050.94 (6)C7—H7A0.97
C4—C51.521 (4)C7—H7B0.97
C4—C31.536 (4)C5—H5A0.97
C4—C11.542 (4)C5—H5B0.97
C4—H40.98
C6—O1—C1110.7 (2)O3—C3—C4110.0 (2)
C3—O3—H03105 (3)O3—C3—C2113.8 (2)
C2—O4—H04106 (2)C4—C3—C289.5 (2)
C7—O5—H05107 (3)O3—C3—H3113.7
C5—C4—C3119.0 (3)C4—C3—H3113.7
C5—C4—C1104.3 (2)C2—C3—H3113.7
C3—C4—C189.6 (2)O2—C6—O1120.7 (3)
C5—C4—H4113.6O2—C6—C5127.9 (3)
C3—C4—H4113.6O1—C6—C5111.4 (3)
C1—C4—H4113.6O5—C7—C1109.7 (2)
O1—C1—C7108.6 (2)O5—C7—H7A109.7
O1—C1—C2112.9 (2)C1—C7—H7A109.7
C7—C1—C2118.7 (2)O5—C7—H7B109.7
O1—C1—C4107.4 (2)C1—C7—H7B109.7
C7—C1—C4118.4 (2)H7A—C7—H7B108.2
C2—C1—C489.5 (2)C6—C5—C4106.0 (3)
O4—C2—C1117.7 (2)C6—C5—H5A110.5
O4—C2—C3116.0 (2)C4—C5—H5A110.5
C1—C2—C389.6 (2)C6—C5—H5B110.5
O4—C2—H2110.7C4—C5—H5B110.5
C1—C2—H2110.7H5A—C5—H5B108.7
C3—C2—H2110.7
C6—O1—C1—C7133.5 (3)C1—C4—C3—O3105.2 (2)
C6—O1—C1—C292.7 (3)C5—C4—C3—C296.2 (3)
C6—O1—C1—C44.4 (3)C1—C4—C3—C210.0 (2)
C5—C4—C1—O14.0 (3)O4—C2—C3—O319.2 (3)
C3—C4—C1—O1123.9 (2)C1—C2—C3—O3101.7 (2)
C5—C4—C1—C7127.3 (3)O4—C2—C3—C4130.9 (2)
C3—C4—C1—C7112.7 (3)C1—C2—C3—C410.0 (2)
C5—C4—C1—C2109.9 (2)C1—O1—C6—O2176.5 (3)
C3—C4—C1—C210.0 (2)C1—O1—C6—C52.9 (3)
O1—C1—C2—O4121.8 (2)O1—C1—C7—O560.9 (3)
C7—C1—C2—O46.9 (4)C2—C1—C7—O5168.4 (2)
C4—C1—C2—O4129.4 (3)C4—C1—C7—O561.8 (3)
O1—C1—C2—C3118.7 (2)O2—C6—C5—C4179.2 (3)
C7—C1—C2—C3112.5 (3)O1—C6—C5—C40.3 (4)
C4—C1—C2—C310.0 (2)C3—C4—C5—C6100.0 (3)
C5—C4—C3—O3148.6 (3)C1—C4—C5—C62.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H04···O3i0.85 (4)1.84 (4)2.688 (4)178 (4)
O3—H03···O4ii0.93 (4)1.78 (5)2.706 (3)173 (4)
O5—H05···O5iii0.94 (6)1.75 (6)2.673 (3)165 (4)
Symmetry codes: (i) x, y, z1; (ii) y+1, xy1, z+1/3; (iii) x+y+2, x+2, z1/3.
 

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