Literature DB >> 22589931

3,3'-Dihy-droxy-6,6'-bis-(hy-droxy-meth-yl)-2,2'-(pentane-1,1-di-yl)di-4H-pyran-4-one.

Mu-Song Liu, Pan-Pan Hu, Tao Zhou.   

Abstract

In the title mol-ecule, C(17)H(20)O(8), the two pyran rings form a dihedral angle of 61.2 (2)°. The two hy-droxy-methyl groups are each disordered over two sets of sites in a 0.764 (3):0.236 (3) ratio. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the ac plane.

Entities:  

Year:  2012        PMID： 22589931      PMCID： PMC3344022          DOI： 10.1107/S1600536812010276

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the biological properties of kojic acid, see: Kobayashi et al. (1995 ▶). For related structures, see: Nurchi et al. (2010 ▶); Kakkar & Singh (2011 ▶); Lokaj et al. (1991 ▶). For the preparation of the title compound, see: Barham & Nathan Reed (1938 ▶).

Experimental

Crystal data

C17H20O8 M = 352.33 Triclinic, a = 6.4234 (3) Å b = 9.2394 (4) Å c = 15.8494 (7) Å α = 79.993 (1)° β = 86.689 (2)° γ = 66.622 (1)° V = 850.22 (7) Å3 Z = 2 Mo Kα radiation μ = 0.11 mm−1 T = 296 K 0.49 × 0.47 × 0.33 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.938, T max = 0.965 8442 measured reflections 3840 independent reflections 2907 reflections with I > 2σ(I) R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.120 S = 1.00 3840 reflections 251 parameters 6 restraints H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.30 e Å−3 Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia,1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010276/cv5255sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010276/cv5255Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812010276/cv5255Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H20O8Z = 2
Mr = 352.33F(000) = 372
Triclinic, P1Dx = 1.376 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.4234 (3) ÅCell parameters from 6451 reflections
b = 9.2394 (4) Åθ = 3.3–27.4°
c = 15.8494 (7) ŵ = 0.11 mm−1
α = 79.993 (1)°T = 296 K
β = 86.689 (2)°Chunk, yellow
γ = 66.622 (1)°0.49 × 0.47 × 0.33 mm
V = 850.22 (7) Å3
Rigaku R-AXIS RAPID/ZJUG diffractometer3840 independent reflections
Radiation source: rotating anode2907 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Detector resolution: 10.00 pixels mm-1θmax = 27.4°, θmin = 3.3°
ω scansh = −8→8
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −11→10
Tmin = 0.938, Tmax = 0.965l = −20→20
8442 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0554P)2 + 0.2871P] where P = (Fo2 + 2Fc2)/3
3840 reflections(Δ/σ)max < 0.001
251 parametersΔρmax = 0.30 e Å−3
6 restraintsΔρmin = −0.30 e Å−3
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.
xyzUiso*/UeqOcc. (<1)
O10.70599 (16)0.37814 (12)0.33797 (6)0.0343 (2)
O20.24351 (19)0.37234 (15)0.52086 (7)0.0489 (3)
O30.10419 (18)0.56659 (15)0.36549 (7)0.0499 (3)
H30.03030.56170.40910.075*
O50.10800 (19)0.56285 (16)0.11434 (8)0.0534 (3)
H50.03660.55940.07400.080*
O60.2475 (2)0.35803 (17)−0.00299 (8)0.0562 (3)
O70.70230 (17)0.35409 (12)0.16422 (6)0.0381 (3)
O4A1.1115 (3)0.1209 (2)0.50117 (12)0.0591 (5)0.764 (3)
H4A1.13800.18830.52090.089*0.764 (3)
O8A1.1284 (3)0.0846 (2)0.04825 (13)0.0635 (6)0.764 (3)
H8A1.15800.15430.01690.095*0.764 (3)
O4B1.0634 (8)0.0558 (6)0.3693 (3)0.0474 (14)0.236 (3)
H4B1.0161−0.00840.39680.071*0.236 (3)
O8B1.061 (2)−0.0030 (16)0.0999 (9)0.153 (5)0.236 (3)
H8B1.03230.00710.04900.230*0.236 (3)
C10.7734 (2)0.28416 (17)0.41491 (9)0.0348 (3)
C20.6275 (3)0.27937 (18)0.47792 (9)0.0375 (3)
H20.68110.21350.53010.045*
C30.3903 (2)0.37414 (17)0.46608 (9)0.0347 (3)
C40.3252 (2)0.47378 (17)0.38243 (9)0.0329 (3)
C50.4816 (2)0.47156 (16)0.32159 (8)0.0302 (3)
C61.0238 (3)0.1844 (2)0.41614 (11)0.0474 (4)
H6A1.05250.09710.38480.057*0.764 (3)
H6B1.10220.24940.38730.057*0.764 (3)
H6C1.10340.24660.38770.057*0.236 (3)
H6D1.07880.14610.47550.057*0.236 (3)
C70.4372 (2)0.56545 (17)0.23201 (8)0.0331 (3)
H70.27590.63620.22790.040*
C80.4808 (2)0.45696 (17)0.16640 (8)0.0332 (3)
C90.3266 (3)0.46005 (18)0.11099 (9)0.0363 (3)
C100.3925 (3)0.35414 (19)0.04794 (9)0.0400 (3)
C110.6259 (3)0.24898 (19)0.04981 (10)0.0437 (4)
H110.67900.17800.01090.052*
C120.7702 (3)0.25138 (18)0.10724 (10)0.0407 (4)
C131.0161 (3)0.1441 (2)0.12089 (14)0.0593 (5)
H13A1.09330.20270.14160.071*0.764 (3)
H13B1.02850.05440.16540.071*0.764 (3)
H13C1.11330.18950.08830.071*0.236 (3)
H13D1.05870.12150.18120.071*0.236 (3)
C140.5730 (3)0.67220 (18)0.21157 (9)0.0396 (3)
H14A0.73360.60510.21780.047*
H14B0.54440.72440.15230.047*
C150.5152 (3)0.79877 (19)0.26837 (10)0.0421 (4)
H15A0.55010.74690.32750.050*
H15B0.35370.86380.26400.050*
C160.6444 (4)0.9060 (2)0.24434 (13)0.0565 (5)
H16A0.80570.84080.25040.068*
H16B0.61360.95420.18450.068*
C170.5856 (5)1.0365 (3)0.29752 (16)0.0846 (8)
H17A0.43091.10970.28630.127*
H17B0.68391.09270.28300.127*
H17C0.60460.99060.35720.127*
U11U22U33U12U13U23
O10.0301 (5)0.0425 (6)0.0298 (5)−0.0143 (4)0.0034 (4)−0.0054 (4)
O20.0423 (6)0.0612 (7)0.0361 (6)−0.0176 (6)0.0120 (5)−0.0004 (5)
O30.0323 (6)0.0651 (8)0.0361 (6)−0.0075 (5)0.0071 (4)0.0030 (5)
O50.0355 (6)0.0775 (9)0.0462 (7)−0.0136 (6)−0.0004 (5)−0.0285 (6)
O60.0540 (7)0.0746 (9)0.0452 (7)−0.0240 (6)−0.0054 (5)−0.0247 (6)
O70.0378 (6)0.0412 (6)0.0340 (5)−0.0127 (5)0.0010 (4)−0.0101 (4)
O4A0.0509 (10)0.0545 (10)0.0667 (11)−0.0207 (8)−0.0180 (8)0.0091 (8)
O8A0.0518 (10)0.0561 (11)0.0838 (14)−0.0127 (9)0.0167 (9)−0.0404 (10)
O4B0.038 (3)0.037 (3)0.062 (3)−0.008 (2)0.009 (2)−0.014 (2)
O8B0.153 (5)0.153 (5)0.154 (5)−0.060 (2)0.0009 (10)−0.0263 (13)
C10.0354 (7)0.0357 (7)0.0338 (7)−0.0140 (6)−0.0016 (6)−0.0066 (6)
C20.0399 (8)0.0384 (8)0.0306 (7)−0.0136 (6)−0.0006 (6)−0.0007 (6)
C30.0393 (8)0.0364 (7)0.0302 (7)−0.0170 (6)0.0054 (6)−0.0066 (6)
C40.0318 (7)0.0363 (7)0.0301 (7)−0.0130 (6)0.0024 (5)−0.0058 (6)
C50.0312 (7)0.0334 (7)0.0282 (6)−0.0141 (6)0.0012 (5)−0.0071 (5)
C60.0351 (8)0.0514 (9)0.0512 (9)−0.0134 (7)−0.0007 (7)−0.0052 (8)
C70.0350 (7)0.0381 (7)0.0256 (6)−0.0136 (6)0.0025 (5)−0.0064 (5)
C80.0349 (7)0.0377 (7)0.0274 (6)−0.0157 (6)0.0044 (5)−0.0046 (6)
C90.0369 (8)0.0450 (8)0.0283 (7)−0.0179 (7)0.0036 (6)−0.0067 (6)
C100.0471 (9)0.0484 (9)0.0293 (7)−0.0235 (7)0.0023 (6)−0.0082 (6)
C110.0541 (10)0.0420 (8)0.0358 (8)−0.0171 (7)0.0047 (7)−0.0140 (7)
C120.0460 (9)0.0372 (8)0.0362 (8)−0.0134 (7)0.0047 (6)−0.0077 (6)
C130.0489 (10)0.0527 (10)0.0658 (12)−0.0064 (8)0.0031 (9)−0.0169 (9)
C140.0500 (9)0.0420 (8)0.0309 (7)−0.0233 (7)0.0081 (6)−0.0063 (6)
C150.0520 (9)0.0409 (8)0.0358 (8)−0.0207 (7)0.0033 (7)−0.0075 (6)
C160.0716 (12)0.0488 (10)0.0576 (11)−0.0329 (9)0.0096 (9)−0.0106 (8)
C170.129 (2)0.0774 (15)0.0786 (15)−0.0695 (16)0.0189 (15)−0.0289 (12)
O1—C11.3502 (17)C6—H6B0.9700
O1—C51.3669 (16)C6—H6C0.9553
O2—C31.2474 (17)C6—H6D0.9795
O3—C41.3492 (17)C7—C81.5069 (19)
O3—H30.8200C7—C141.542 (2)
O5—C91.3518 (18)C7—H70.9800
O5—H50.8200C8—C91.350 (2)
O6—C101.2531 (19)C9—C101.448 (2)
O7—C121.3529 (18)C10—C111.426 (2)
O7—C81.3641 (17)C11—C121.345 (2)
O4A—C61.424 (2)C11—H110.9300
O4A—H4A0.8200C12—C131.499 (2)
O4A—H6D0.4491C13—H13A0.9700
O8A—C131.399 (3)C13—H13B0.9700
O8A—H8A0.8200C13—H13C0.9635
O8A—H13C1.2178C13—H13D0.9733
O4B—C61.439 (5)C14—C151.516 (2)
O4B—H4B0.8200C14—H14A0.9700
O8B—C131.369 (13)C14—H14B0.9700
O8B—H8B0.8200C15—C161.517 (2)
C1—C21.337 (2)C15—H15A0.9700
C1—C61.503 (2)C15—H15B0.9700
C2—C31.428 (2)C16—C171.504 (3)
C2—H20.9300C16—H16A0.9700
C3—C41.4541 (19)C16—H16B0.9700
C4—C51.3484 (19)C17—H17A0.9600
C5—C71.5073 (19)C17—H17B0.9600
C6—H6A0.9700C17—H17C0.9600
C1—O1—C5120.29 (11)O6—C10—C11124.42 (15)
C4—O3—H3109.5O6—C10—C9120.11 (15)
C9—O5—H5109.5C11—C10—C9115.47 (13)
C12—O7—C8120.36 (12)C12—C11—C10120.66 (14)
C6—O4A—H4A109.5C12—C11—H11119.7
H4A—O4A—H6D104.7C10—C11—H11119.7
C13—O8A—H8A109.5C11—C12—O7121.98 (14)
H8A—O8A—H13C70.3C11—C12—C13127.48 (15)
C6—O4B—H4B109.5O7—C12—C13110.50 (14)
C13—O8B—H8B109.5O8B—C13—O8A52.8 (6)
C2—C1—O1122.32 (13)O8B—C13—C12111.3 (6)
C2—C1—C6126.71 (14)O8A—C13—C12115.07 (17)
O1—C1—C6110.89 (13)O8B—C13—H13A140.2
C1—C2—C3120.82 (13)O8A—C13—H13A108.5
C1—C2—H2119.6C12—C13—H13A108.5
C3—C2—H2119.6O8B—C13—H13B59.8
O2—C3—C2124.45 (13)O8A—C13—H13B108.5
O2—C3—C4120.46 (13)C12—C13—H13B108.5
C2—C3—C4115.07 (12)H13A—C13—H13B107.5
O3—C4—C5120.03 (12)O8B—C13—H13C108.9
O3—C4—C3119.06 (12)O8A—C13—H13C58.6
C5—C4—C3120.89 (13)C12—C13—H13C112.0
C4—C5—O1120.60 (12)H13A—C13—H13C53.5
C4—C5—C7126.41 (13)H13B—C13—H13C139.0
O1—C5—C7112.99 (11)O8B—C13—H13D104.3
O4A—C6—O4B109.7 (3)O8A—C13—H13D133.4
O4A—C6—C1111.96 (15)C12—C13—H13D111.1
O4B—C6—C1108.5 (2)H13A—C13—H13D60.5
O4A—C6—H6A109.2H13B—C13—H13D48.6
C1—C6—H6A109.2H13C—C13—H13D108.8
O4A—C6—H6B109.2C15—C14—C7113.65 (12)
O4B—C6—H6B108.1C15—C14—H14A108.8
C1—C6—H6B109.2C7—C14—H14A108.8
H6A—C6—H6B107.9C15—C14—H14B108.8
O4A—C6—H6C109.0C7—C14—H14B108.8
O4B—C6—H6C107.4H14A—C14—H14B107.7
C1—C6—H6C110.2C14—C15—C16112.37 (14)
H6A—C6—H6C107.1C14—C15—H15A109.1
O4B—C6—H6D112.6C16—C15—H15A109.1
C1—C6—H6D109.6C14—C15—H15B109.1
H6A—C6—H6D112.1C16—C15—H15B109.1
H6B—C6—H6D108.8H15A—C15—H15B107.9
H6C—C6—H6D108.6C17—C16—C15113.87 (17)
C5—C7—C8111.20 (12)C17—C16—H16A108.8
C5—C7—C14112.71 (12)C15—C16—H16A108.8
C8—C7—C14110.77 (11)C17—C16—H16B108.8
C5—C7—H7107.3C15—C16—H16B108.8
C8—C7—H7107.3H16A—C16—H16B107.7
C14—C7—H7107.3C16—C17—H17A109.5
C9—C8—O7120.75 (13)C16—C17—H17B109.5
C9—C8—C7126.05 (13)H17A—C17—H17B109.5
O7—C8—C7113.13 (12)C16—C17—H17C109.5
C8—C9—O5119.76 (13)H17A—C17—H17C109.5
C8—C9—C10120.76 (14)H17B—C17—H17C109.5
O5—C9—C10119.48 (13)
C5—O1—C1—C2−0.8 (2)C5—C7—C8—C9118.54 (16)
C5—O1—C1—C6176.06 (12)C14—C7—C8—C9−115.30 (16)
O1—C1—C2—C30.4 (2)C5—C7—C8—O7−64.36 (15)
C6—C1—C2—C3−175.94 (14)C14—C7—C8—O761.80 (15)
C1—C2—C3—O2177.73 (16)O7—C8—C9—O5179.93 (13)
C1—C2—C3—C4−0.6 (2)C7—C8—C9—O5−3.2 (2)
O2—C3—C4—O31.3 (2)O7—C8—C9—C100.1 (2)
C2—C3—C4—O3179.63 (13)C7—C8—C9—C10176.96 (13)
O2—C3—C4—C5−177.25 (14)C8—C9—C10—O6179.85 (15)
C2—C3—C4—C51.1 (2)O5—C9—C10—O60.0 (2)
O3—C4—C5—O1179.94 (13)C8—C9—C10—C110.5 (2)
C3—C4—C5—O1−1.5 (2)O5—C9—C10—C11−179.41 (14)
O3—C4—C5—C70.1 (2)O6—C10—C11—C12−179.32 (16)
C3—C4—C5—C7178.57 (13)C9—C10—C11—C120.0 (2)
C1—O1—C5—C41.4 (2)C10—C11—C12—O7−1.1 (2)
C1—O1—C5—C7−178.71 (12)C10—C11—C12—C13176.58 (17)
C2—C1—C6—O4A−20.6 (2)C8—O7—C12—C111.7 (2)
O1—C1—C6—O4A162.71 (14)C8—O7—C12—C13−176.37 (14)
C2—C1—C6—O4B100.7 (3)C11—C12—C13—O8B−29.2 (7)
O1—C1—C6—O4B−76.1 (3)O7—C12—C13—O8B148.7 (7)
C4—C5—C7—C8−111.66 (16)C11—C12—C13—O8A28.5 (3)
O1—C5—C7—C868.45 (15)O7—C12—C13—O8A−153.56 (17)
C4—C5—C7—C14123.26 (16)C5—C7—C14—C15−61.92 (17)
O1—C5—C7—C14−56.62 (16)C8—C7—C14—C15172.77 (13)
C12—O7—C8—C9−1.1 (2)C7—C14—C15—C16−177.67 (14)
C12—O7—C8—C7−178.40 (12)C14—C15—C16—C17178.09 (18)
D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.821.962.7275 (15)155
O3—H3···O20.822.322.7440 (15)113
O5—H5···O6ii0.822.002.7488 (16)151
O5—H5···O60.822.322.7436 (16)113
O4A—H4A···O2iii0.822.072.839 (2)157
O8A—H8A···O6iii0.822.152.894 (2)152
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O3—H3⋯O2i0.821.962.7275 (15)155
O3—H3⋯O20.822.322.7440 (15)113
O5—H5⋯O6ii0.822.002.7488 (16)151
O5—H5⋯O60.822.322.7436 (16)113
O4A—H4A⋯O2iii0.822.072.839 (2)157
O8A—H8A⋯O6iii0.822.152.894 (2)152

Symmetry codes: (i) ; (ii) ; (iii) .

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1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

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