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2,3,4-Trihy-droxy-benzoic acid 0.25-hydrate.
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MedLine Citation:
PMID:  22412689     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
The asymmetric unit of the title compound, C(7)H(6)O(5)·0.25H(2)O, contains two mol-ecules of 2,3,4-trihy-droxy-benzoic acid, with similar conformations, and one water mol-ecule which lies on a twofold rotation axis. Both acid mol-ecules are essentially planar [maximum r.m.s deviations = 0.0324 (2) and 0.0542 (3) Å for the two acid molecules]. The mol-ecular conformations are stabilized by intra-molecular O(phenol)-H⋯O(carbox-yl/phenol) inter-actions. A cyclic inter-molecular association is formed between the two acid and one water mol-ecule [graph set R(3) (3)(12)] involving O-H⋯O hydrogen bonds. The two acid mol-ecules are further linked through a cyclic R(2) (2)(8) carb-oxy-lic acid hydrogen-bonding association, which together with inter-molecular O-H⋯O hydrogen-bonding inter-actions involving the phenol groups and the water mol-ecule, and weak π-π inter-actions [minimum ring centroid separation = 3.731 (3) Å], give a three-dimensional network.
Authors:
Jin-Hang Li; Fu-Yue Dong; Fang Cai; Xiao-Feng Yuan; Ren-Wang Jiang
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Publication Detail:
Type:  Journal Article     Date:  2012-02-24
Journal Detail:
Title:  Acta crystallographica. Section E, Structure reports online     Volume:  68     ISSN:  1600-5368     ISO Abbreviation:  Acta Crystallogr Sect E Struct Rep Online     Publication Date:  2012 Mar 
Date Detail:
Created Date:  2012-03-13     Completed Date:  2012-10-02     Revised Date:  2013-03-01    
Medline Journal Info:
Nlm Unique ID:  101089178     Medline TA:  Acta Crystallogr Sect E Struct Rep Online     Country:  United States    
Other Details:
Languages:  eng     Pagination:  o825-6     Citation Subset:  -    
Affiliation:
Guangdong Province Key Laboratory of Pharmacodynamic Constituents of, Traditional Chinese Medicine and New Drugs Research, Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou 510632, People's Republic of China.
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Journal ID (nlm-ta): Acta Crystallogr Sect E Struct Rep Online
Journal ID (publisher-id): Acta Cryst. E
ISSN: 1600-5368
Publisher: International Union of Crystallography
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A full version of this article is available from Crystallography Journals Online.© Li et al. 2012
open-access:
Received Day: 04 Month: 2 Year: 2012
Accepted Day: 16 Month: 2 Year: 2012
collection publication date: Day: 01 Month: 3 Year: 2012
Electronic publication date: Day: 24 Month: 2 Year: 2012
pmc-release publication date: Day: 24 Month: 2 Year: 2012
Volume: 68 Issue: Pt 3
First Page: o825 Last Page: o826
ID: 3297886
PubMed Id: 22412689
Publisher Id: zs2181
DOI: 10.1107/S160053681200709X
Coden: ACSEBH
Publisher Item Identifier: S160053681200709X

2,3,4-Trihy­droxy­benzoic acid 0.25-hydrate Alternate Title:C7H6O5·0.25H2O
Jin-Hang Lia
Fu-Yue Donga
Fang Caia
Xiao-Feng Yuana
Ren-Wang Jianga*
aGuangdong Province Key Laboratory of Pharmacodynamic Constituents of, Traditional Chinese Medicine and New Drugs Research, Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou 510632, People’s Republic of China
Correspondence: Correspondence e-mail: trwjiang@jnu.edu.cn

Related literature  

For the natural distribution of 2,3,4-trihy­droxy­benzoic acid, see: Zhai et al. (2010); Xu & Chang (2010). For its anti­oxidant and anti­bacterial activities, see: Kodama et al. (2007); Friedman et al. (2003). For the inhibition of xanthine oxidase, see: Chang et al. (1995). For the crystal structure of the dihydrate pseudopolymorph, see: Prior & Sharp (2010). For π–π inter­actions in gallic acid pyridine monosolvate and in natural flavonoids, see: Dong et al. (2011); Jiang et al. (2009, 2002). For graph-set analysis, see: Etter et al. (1990); Bernstein et al. (1995).[Chemical Structure ID: scheme1]


Experimental  
Crystal data  

  • C7H6O5·0.25H2O
  • Mr = 174.62
  • Orthorhombic,
  • a = 11.8364 (12) Å
  • b = 32.598 (3) Å
  • c = 3.7306 (4) Å
  • V = 1439.4 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.14 mm−1
  • T = 291 K
  • 0.42 × 0.28 × 0.20 mm

Data collection  

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004) Tmin = 0.874, Tmax = 1.000
  • 7863 measured reflections
  • 2552 independent reflections
  • 2010 reflections with I > 2σ(I)
  • Rint = 0.060

Refinement  

  • R[F2 > 2σ(F2)] = 0.036
  • wR(F2) = 0.090
  • S = 0.97
  • 2552 reflections
  • 222 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).


Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681200709X/zs2181sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200709X/zs2181Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200709X/zs2181Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report


Notes

fnu1Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2181).

This work was supported by a grant from the New Century Excellent Talents Scheme of the Ministry of Education (grant No. NCET-08–0612), the Guangdong High Level Talent Scheme (RWJ) and the Fundamental Research Funds for the Central Universities (grant No. 21609202).

supplementary crystallographic information
Comment

2,3,4-Trihydroxybenzoic acid is a polyphenolic acid which has been isolated from Pachysandra terminalis (Zhai et al., 2010) and the lentil (Xu & Chang, 2010). It has been found to show antioxidant (Kodama et al., 2007) and antibacterial activities (Friedman et al., 2003) and also to inhibit the xanthine oxidase enzyme (Chang et al., 1995). This compound contains two of the most common functional groups in natural products: the carboxylic acid and the phenolic groups. The dihydrate pseudopolymorph of the acid with a space group P-1 has previusly been reported (Prior & Sharp, 2010). In this study, we report the structure of the second pseudopolymorph, the partial hydrate C7H6O5 . 0.25H2O.

The asymmetric unit of the title compound contains two molecules of 2,3,4-trihydroxybenzoic acid [(1) and (2)] with similar conformations, and one water molecule of solvation which lies on a crystallographic twofold rotation axis (Fig. 1). Both acid molecules are essentially planar [maximum r.m.s deviation 0.0324 (2) and 0.0542 (3) Å for the two acid molecules], with a dihedral angle of 49.4 (3)° between the planes. The molecular conformation of the acid molecules is stabilized by a number of intramolecular phenolic O—H···O interactions (Table 1).

The water molecule and the acid molecules are linked through O—H···O hydrogen bonds (Table 1) with both acting as donors and acceptors, giving a cyclic association [graph set R33(12) (Etter et al., 1990; Bernstein et al., 1995)]. The 2,3,4-trihydroxybenzoic acid molecules form head-to-head pairs through intermolecular hydrogen bonds [graph set R22(8). The molecular pairs are further extended into chains through hydrogen bond O2–H···O2'i , while adjacent chains are connected via hydrogen bond O3–H···O3'ii into a three-dimensional network (Fig. 2) [for symmetry codes (i) and (ii), see Table 1]. It is noteworthy that aromatic π–π associations also play an important role in the molecular packing. Adjacent 2,3,4-trihydroxybenzoic acid molecules form stacks which extend down the c-axis giving weak π–π interactions [minimum ring centroid separation, 3.731 (3) Å], which is larger than that in the dihydrate form of the acid (Prior & Sharp, 2010) and in gallic acid pyridine monosolvate (Dong et al., 2011), but comparable with those in natural flavonoids (Jiang et al., 2002, 2009).

Experimental

2,3,4-Trihydroxybenzoic acid (purity >98%) was purchased from the Sigma-Aldrich Company. Sample of 34 mg (0.2 mmol) was dissolved in methanol (1.5 ml) in a tube (4 ml) and sealed by parafilm. Light brown crystals were formed after three days at room temperature.

Refinement

The C-bound H atoms were positioned geometrically and were included in the refinement in the riding-model approximation, with C—H = 0.96 Å (methyl C) and Uiso(H) = 1.5Ueq(C); 0.97 Å (methylene C) and Uiso(H) = 1.2Ueq(C); 0.93 Å (aryl H) and Uiso(H)= 1.2Ueq(C); O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O).

Figures
Crystal data
Data collection
Refinement
Special details
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
Atomic displacement parameters (Å2)
Geometric parameters (Å, º)
Hydrogen-bond geometry (Å, º)

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


References
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew Chem. Int. Ed. Engl.34, 1555–1573.
Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
Chang, W. S., Yan, G. F. & Chiang, H. C. (1995). Anticancer Res.15, 2097–2100.
Dong, F.-Y., Wu, J., Tian, H.-Y., Ye, Q.-M. & Jiang, R.-W. (2011). Acta Cryst. E67, o3096.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262.
Friedman, M., Henika, P. R. & Mandrell, R. E. (2003). J. Food Prot.66, 1811–1821.
Jiang, R. W., Wang, Y., Gao, H., Zhang, D. M. & Ye, W. C. (2009). J. Mol. Struct.920, 383–386.
Jiang, R. W., Ye, W. C., Woo, K. Y., Du, J., Che, C. T., But, P. P. H. & Mak, T. C. W. (2002). J. Mol. Struct.642, 77–84.
Kodama, A., Shibano, H. & Kawabata, J. (2007). Biosci. Biotech. Biochem.71, 1731–1734.
Prior, T. J. & Sharp, A. J. (2010). J. Chem. Crystallogr.40, 630–633.
Sheldrick, G. M. (2004). SADABS University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Siemens (1998). XP Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Xu, B. & Chang, S. K. C. (2010). J. Agric. Food Chem.58, 1509–1517.
Zhai, H., Li, C., Tang, S. & Duan, H. (2010). Chin. J. Chin. Mat. Med.35, 1820–1823.

Figures

[Figure ID: Fap1]
Fig. 1. 

An ORTEP plot of the asymmetric unit of the title compound with atoms shown as 30% probability ellipsoids. The water molecule lies on a crystallographic twofold rotation axis and hydrogen bonds are shown as dashed lines.



[Figure ID: Fap2]
Fig. 2. 

Packing diagram viewed down the c-axis showing hydrogen bonds as dashed lines.



Tables
[TableWrap ID: d1e226]
C7H6O5·0.25H2O F(000) = 724
Mr = 174.62 Dx = 1.612 Mg m3
Orthorhombic, P21212 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab Cell parameters from 2552 reflections
a = 11.8364 (12) Å θ = 2.1–50.0°
b = 32.598 (3) Å µ = 0.14 mm1
c = 3.7306 (4) Å T = 291 K
V = 1439.4 (3) Å3 Prism, light brown
Z = 8 0.42 × 0.28 × 0.20 mm

[TableWrap ID: d1e352]
Bruker SMART 1000 CCD diffractometer 2552 independent reflections
Radiation source: fine-focus sealed tube 2010 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.060
ω scan θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) h = −13→14
Tmin = 0.874, Tmax = 1.000 k = −38→34
7863 measured reflections l = −4→4

[TableWrap ID: d1e466]
Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090 H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0443P)2] where P = (Fo2 + 2Fc2)/3
2552 reflections (Δ/σ)max < 0.001
222 parameters Δρmax = 0.17 e Å3
0 restraints Δρmin = −0.15 e Å3

[TableWrap ID: d1e620]
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

[TableWrap ID: d1e665]
x y z Uiso*/Ueq
O1W 0.5000 0.0000 −0.1102 (7) 0.0395 (6)
H1WA 0.5263 0.0173 0.0258 0.059*
O1 0.65345 (12) 0.12870 (4) 0.2193 (5) 0.0334 (4)
H1A 0.6637 0.1534 0.1900 0.040*
O2 0.65656 (13) 0.04688 (4) 0.3549 (4) 0.0323 (4)
H2A 0.6145 0.0640 0.4444 0.039*
O3 0.84576 (14) 0.00203 (5) 0.2010 (5) 0.0445 (5)
H3A 0.7859 −0.0048 0.2940 0.053*
O4 0.75826 (14) 0.19200 (4) −0.0346 (6) 0.0429 (5)
O5 0.93058 (15) 0.18491 (4) −0.2704 (6) 0.0481 (5)
H5B 0.9243 0.2098 −0.2919 0.058*
C1 0.84467 (19) 0.12653 (6) −0.0250 (7) 0.0273 (5)
C2 0.74982 (19) 0.10787 (6) 0.1337 (6) 0.0245 (5)
C3 0.74932 (18) 0.06626 (6) 0.2074 (6) 0.0254 (5)
C4 0.84311 (19) 0.04271 (6) 0.1272 (7) 0.0295 (5)
C5 0.9374 (2) 0.06046 (7) −0.0324 (7) 0.0330 (6)
H5A 0.9998 0.0444 −0.0891 0.040*
C6 0.9383 (2) 0.10180 (7) −0.1064 (7) 0.0313 (6)
H6A 1.0018 0.1135 −0.2117 0.038*
C7 0.8406 (2) 0.17017 (7) −0.1079 (7) 0.0310 (6)
O1' 0.49399 (13) 0.17376 (4) −0.2824 (5) 0.0359 (4)
H1'A 0.4856 0.1982 −0.3270 0.043*
O2' 0.49999 (12) 0.09083 (4) −0.2151 (5) 0.0308 (4)
H2'A 0.5380 0.1075 −0.1033 0.037*
O3' 0.32290 (14) 0.04439 (4) −0.4474 (5) 0.0397 (5)
H3'A 0.3817 0.0378 −0.3464 0.048*
O4' 0.39072 (15) 0.23703 (5) −0.5434 (6) 0.0446 (5)
O5' 0.22055 (15) 0.23003 (5) −0.7935 (6) 0.0506 (5)
H5'B 0.2294 0.2547 −0.8259 0.061*
C1' 0.3088 (2) 0.17066 (7) −0.5659 (7) 0.0293 (6)
C2' 0.40325 (19) 0.15242 (6) −0.4052 (6) 0.0271 (6)
C3' 0.40863 (19) 0.11019 (6) −0.3646 (6) 0.0267 (5)
C4' 0.31874 (19) 0.08593 (6) −0.4795 (7) 0.0281 (6)
C5' 0.22322 (19) 0.10389 (7) −0.6322 (7) 0.0328 (6)
H5'A 0.1630 0.0876 −0.7056 0.039*
C6' 0.2185 (2) 0.14569 (7) −0.6737 (7) 0.0336 (6)
H6'A 0.1546 0.1576 −0.7746 0.040*
C7' 0.3098 (2) 0.21492 (7) −0.6310 (7) 0.0349 (6)

[TableWrap ID: d1e1218]
U11 U22 U33 U12 U13 U23
O1W 0.0469 (15) 0.0229 (11) 0.0486 (16) −0.0056 (10) 0.000 0.000
O1 0.0299 (9) 0.0177 (7) 0.0527 (11) 0.0023 (6) 0.0057 (9) 0.0020 (8)
O2 0.0280 (9) 0.0212 (8) 0.0475 (11) 0.0003 (6) 0.0064 (8) 0.0020 (8)
O3 0.0386 (10) 0.0215 (8) 0.0734 (13) 0.0038 (7) 0.0121 (10) 0.0077 (10)
O4 0.0398 (11) 0.0244 (8) 0.0644 (13) −0.0006 (8) 0.0084 (10) 0.0075 (9)
O5 0.0463 (11) 0.0268 (9) 0.0713 (14) −0.0031 (8) 0.0157 (11) 0.0094 (10)
C1 0.0298 (13) 0.0244 (11) 0.0278 (13) −0.0029 (10) −0.0040 (11) 0.0009 (11)
C2 0.0265 (12) 0.0208 (11) 0.0261 (13) 0.0014 (9) −0.0058 (11) −0.0024 (10)
C3 0.0285 (13) 0.0211 (11) 0.0268 (12) −0.0056 (9) −0.0017 (11) 0.0004 (10)
C4 0.0334 (14) 0.0193 (11) 0.0359 (14) 0.0014 (10) −0.0033 (12) 0.0009 (11)
C5 0.0278 (14) 0.0303 (13) 0.0409 (15) 0.0041 (10) 0.0006 (12) −0.0034 (12)
C6 0.0257 (13) 0.0324 (13) 0.0360 (15) −0.0042 (10) −0.0001 (12) 0.0006 (11)
C7 0.0315 (14) 0.0255 (12) 0.0361 (14) −0.0068 (11) −0.0040 (12) 0.0019 (11)
O1' 0.0346 (9) 0.0185 (7) 0.0546 (11) −0.0032 (6) −0.0058 (10) 0.0011 (8)
O2' 0.0294 (9) 0.0191 (7) 0.0440 (10) 0.0016 (6) −0.0038 (9) 0.0011 (7)
O3' 0.0408 (11) 0.0207 (8) 0.0575 (12) −0.0029 (7) −0.0115 (9) −0.0004 (9)
O4' 0.0476 (12) 0.0208 (8) 0.0655 (14) 0.0004 (8) −0.0142 (10) 0.0057 (9)
O5' 0.0482 (11) 0.0279 (9) 0.0758 (14) 0.0047 (8) −0.0172 (12) 0.0138 (10)
C1' 0.0340 (14) 0.0227 (12) 0.0312 (13) 0.0031 (10) 0.0040 (11) −0.0003 (11)
C2' 0.0295 (13) 0.0221 (12) 0.0297 (14) −0.0024 (10) 0.0035 (12) −0.0021 (10)
C3' 0.0280 (13) 0.0231 (11) 0.0290 (13) 0.0037 (10) 0.0045 (11) 0.0009 (10)
C4' 0.0334 (14) 0.0199 (11) 0.0311 (14) 0.0005 (10) 0.0052 (11) −0.0007 (11)
C5' 0.0297 (14) 0.0299 (12) 0.0388 (15) −0.0033 (10) −0.0005 (12) −0.0019 (12)
C6' 0.0342 (14) 0.0326 (12) 0.0339 (15) 0.0051 (10) −0.0039 (12) 0.0022 (12)
C7' 0.0399 (16) 0.0271 (13) 0.0376 (15) 0.0071 (11) 0.0020 (12) 0.0021 (12)

[TableWrap ID: d1e1702]
O1W—H1WA 0.8200 O1'—C2' 1.359 (3)
O1—C2 1.365 (3) O1'—H1'A 0.8200
O1—H1A 0.8200 O2'—C3' 1.371 (3)
O2—C3 1.381 (3) O2'—H2'A 0.8200
O2—H2A 0.8200 O3'—C4' 1.360 (2)
O3—C4 1.355 (2) O3'—H3'A 0.8200
O3—H3A 0.8200 O4'—C7' 1.243 (3)
O4—C7 1.237 (3) O5'—C7' 1.314 (3)
O5—C7 1.317 (3) O5'—H5'B 0.8200
O5—H5B 0.8200 C1'—C2' 1.401 (3)
C1—C6 1.404 (3) C1'—C6' 1.403 (3)
C1—C2 1.407 (3) C1'—C7' 1.463 (3)
C1—C7 1.457 (3) C2'—C3' 1.386 (3)
C2—C3 1.384 (3) C3'—C4' 1.393 (3)
C3—C4 1.382 (3) C4'—C5' 1.395 (3)
C4—C5 1.391 (3) C5'—C6' 1.373 (3)
C5—C6 1.376 (3) C5'—H5'A 0.9300
C5—H5A 0.9300 C6'—H6'A 0.9300
C6—H6A 0.9300
C2—O1—H1A 109.5 C2'—O1'—H1'A 109.5
C3—O2—H2A 109.5 C3'—O2'—H2'A 109.5
C4—O3—H3A 109.5 C4'—O3'—H3'A 109.5
C7—O5—H5B 109.5 C7'—O5'—H5'B 109.5
C6—C1—C2 118.2 (2) C2'—C1'—C6' 119.0 (2)
C6—C1—C7 122.8 (2) C2'—C1'—C7' 118.9 (2)
C2—C1—C7 119.0 (2) C6'—C1'—C7' 122.1 (2)
O1—C2—C3 115.9 (2) O1'—C2'—C3' 115.8 (2)
O1—C2—C1 123.35 (18) O1'—C2'—C1' 123.89 (18)
C3—C2—C1 120.7 (2) C3'—C2'—C1' 120.3 (2)
O2—C3—C4 118.08 (17) O2'—C3'—C2' 122.5 (2)
O2—C3—C2 122.06 (19) O2'—C3'—C4' 117.79 (18)
C4—C3—C2 119.9 (2) C2'—C3'—C4' 119.7 (2)
O3—C4—C3 121.2 (2) O3'—C4'—C3' 120.7 (2)
O3—C4—C5 118.4 (2) O3'—C4'—C5' 118.9 (2)
C3—C4—C5 120.4 (2) C3'—C4'—C5' 120.4 (2)
C6—C5—C4 119.9 (2) C6'—C5'—C4' 119.7 (2)
C6—C5—H5A 120.0 C6'—C5'—H5'A 120.1
C4—C5—H5A 120.0 C4'—C5'—H5'A 120.1
C5—C6—C1 120.9 (2) C5'—C6'—C1' 120.8 (2)
C5—C6—H6A 119.6 C5'—C6'—H6'A 119.6
C1—C6—H6A 119.6 C1'—C6'—H6'A 119.6
O4—C7—O5 122.0 (2) O4'—C7'—O5' 121.6 (2)
O4—C7—C1 122.7 (2) O4'—C7'—C1' 122.3 (2)
O5—C7—C1 115.3 (2) O5'—C7'—C1' 116.1 (2)
C6—C1—C2—O1 −178.9 (2) C6'—C1'—C2'—O1' −178.2 (2)
C7—C1—C2—O1 −0.8 (3) C7'—C1'—C2'—O1' 4.6 (4)
C6—C1—C2—C3 0.1 (3) C6'—C1'—C2'—C3' 2.1 (4)
C7—C1—C2—C3 178.2 (2) C7'—C1'—C2'—C3' −175.1 (2)
O1—C2—C3—O2 0.7 (3) O1'—C2'—C3'—O2' −0.9 (3)
C1—C2—C3—O2 −178.4 (2) C1'—C2'—C3'—O2' 178.8 (2)
O1—C2—C3—C4 179.6 (2) O1'—C2'—C3'—C4' 179.3 (2)
C1—C2—C3—C4 0.5 (3) C1'—C2'—C3'—C4' −1.0 (4)
O2—C3—C4—O3 −2.0 (3) O2'—C3'—C4'—O3' −0.8 (3)
C2—C3—C4—O3 179.0 (2) C2'—C3'—C4'—O3' 179.0 (2)
O2—C3—C4—C5 177.9 (2) O2'—C3'—C4'—C5' 179.7 (2)
C2—C3—C4—C5 −1.0 (4) C2'—C3'—C4'—C5' −0.5 (4)
O3—C4—C5—C6 −179.1 (2) O3'—C4'—C5'—C6' −178.6 (2)
C3—C4—C5—C6 1.0 (4) C3'—C4'—C5'—C6' 0.9 (4)
C4—C5—C6—C1 −0.4 (4) C4'—C5'—C6'—C1' 0.3 (4)
C2—C1—C6—C5 −0.1 (4) C2'—C1'—C6'—C5' −1.8 (4)
C7—C1—C6—C5 −178.2 (2) C7'—C1'—C6'—C5' 175.3 (2)
C6—C1—C7—O4 −179.6 (2) C2'—C1'—C7'—O4' −1.2 (4)
C2—C1—C7—O4 2.3 (4) C6'—C1'—C7'—O4' −178.3 (2)
C6—C1—C7—O5 1.0 (3) C2'—C1'—C7'—O5' 177.7 (2)
C2—C1—C7—O5 −177.1 (2) C6'—C1'—C7'—O5' 0.6 (4)

[TableWrap ID: d1e2359]
D—H···A D—H H···A D···A D—H···A
O1W—H1WA···O2 0.82 2.19 2.963 (2) 156
O1W—H1WA···O2′ 0.82 2.58 2.987 (3) 112
O1—H1A···O4 0.82 1.88 2.587 (3) 143
O2—H2A···O2′i 0.82 2.05 2.839 (4) 161
O2—H2A···O1 0.82 2.32 2.715 (2) 111
O3—H3A···O3′ii 0.82 2.06 2.828 (3) 155
O3—H3A···O2 0.82 2.29 2.735 (3) 115
O5—H5B···O4′iii 0.82 1.88 2.679 (4) 165
O1′—H1′A···O4′ 0.82 1.87 2.588 (3) 145
O2′—H2′A···O1 0.82 1.95 2.729 (4) 159
O2′—H2′A···O1′ 0.82 2.32 2.716 (2) 110
O3′—H3′A···O1W 0.82 2.06 2.841 (3) 158
O3′—H3′A···O2′ 0.82 2.28 2.727 (4) 115
O5′—H5′B···O4iv 0.82 1.85 2.659 (4) 171


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