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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1189.
Published online 2008 June 7. doi:  10.1107/S1600536808015833
PMCID: PMC2961715

3-Hydroxy­meth­yl-6,8-dimeth­oxy-2H-chromen-2-one

Abstract

The asymmetric unit of the title compound, C12H12O5, contains four independent mol­ecules. In the crystal structure, inter­molecular O—H(...)O hydrogen bonds link the mol­ecules into one-dimensional infinite chains. They are arranged in a nearly parallel fashion along the b axis and stabilized by π–π inter­actions [3.443 (2) Å].

Related literature

For related literature, see: Ayer et al. (1990 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1189-scheme1.jpg

Experimental

Crystal data

  • C12H12O5
  • M r = 236.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1189-efi1.jpg
  • a = 14.6979 (16) Å
  • b = 12.2246 (14) Å
  • c = 23.896 (3) Å
  • β = 95.035 (2)°
  • V = 4277.0 (9) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.12 mm−1
  • T = 173 (2) K
  • 0.49 × 0.42 × 0.25 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.946, T max = 0.972
  • 19027 measured reflections
  • 7927 independent reflections
  • 4460 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.170
  • S = 1.00
  • 7927 reflections
  • 625 parameters
  • H-atom parameters constrained
  • Δρmax = 0.55 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015833/hk2466sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015833/hk2466Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support from the Youth Fund of Guangdong Medical College (grant No. XQ0511).

supplementary crystallographic information

Comment

The title compound was isolated from the endophytic fungus No. 2090 of the mangrove tree from the South China Sea coast. This substance was previously isolated from the organic extracts of the fungus Verticilliumdahliae Kleb (Ayer et al., 1978). However, the structure of the title compound, (I), was previously elucidated on the basic of spectroscopic analysis. For further confirming the analytical results, we report herein its crystal structure.

The asymmetric unit of (I) (Fig. 1) contains four independent molecules.

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into one-dimensional infinite chains (Fig. 2). Morover, they are arranged in nearly parallel fashion along the b axis and stabilized by the π–π interactions.

Experimental

A strain of fungus (No. 2090) was deposited in the Department of Applied Chemistry, Zhongshan University, Guangzhou, People's Republic of China. Culture conditions: GYT medium (glucose 10 g /L, peptone 2 g /L, yeast extract 1 g /L, NaCl 2.5 g /L) and incubation at 298 K for 24 d. For the extraction and separation of the metabolite, the cultures (70 L) of the title compound were filtered through cheesecloth. The filtrate was concentrated to 3 L below 323 K, then extracted five times by shaking with an equal volume of ethyl acetate. The extract was evaporated under reduced pressure below 323 K. The combined organic extracts were subjected to silica-gel column chromatography, eluting with petroleum ether/ethyl acetate, to yield the title compound. Crystals were obtained through evaporation of a methanol solution.

Refinement

H atoms were positioned geometrically, with O—H = 0.84 Å (for OH) and C—H = 0.95, 0.99 and 0.98 Å for aromatic methylene and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C,O), where x = 1.5 for OH H, and x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are omitted for clarity.
Fig. 2.
A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines.

Crystal data

C12H12O5F000 = 1984
Mr = 236.22Dx = 1.467 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5413 reflections
a = 14.6979 (16) Åθ = 2.2–27.0º
b = 12.2246 (14) ŵ = 0.12 mm1
c = 23.896 (3) ÅT = 173 (2) K
β = 95.035 (2)ºBlock, yellow
V = 4277.0 (9) Å30.49 × 0.42 × 0.25 mm
Z = 16

Data collection

Bruker SMART CCD area-detector diffractometer7927 independent reflections
Radiation source: fine-focus sealed tube4460 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.041
T = 173(2) Kθmax = 25.5º
[var phi] and ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −17→16
Tmin = 0.946, Tmax = 0.972k = −6→14
19027 measured reflectionsl = −28→28

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.170  w = 1/[σ2(Fo2) + (0.0977P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
7927 reflectionsΔρmax = 0.55 e Å3
625 parametersΔρmin = −0.34 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.34046 (10)0.06130 (12)0.46126 (6)0.0222 (4)
O20.23122 (10)−0.02976 (13)0.49764 (7)0.0292 (4)
O30.39758 (10)0.25128 (12)0.43110 (7)0.0285 (4)
O40.66666 (11)0.07960 (14)0.36495 (7)0.0357 (5)
O50.36461 (10)−0.32898 (13)0.47854 (8)0.0363 (5)
H50.3374−0.38680.48630.054*
O60.40867 (10)0.01426 (12)0.28271 (6)0.0232 (4)
O70.51833 (10)0.10466 (13)0.24619 (7)0.0303 (4)
O80.34984 (10)−0.17613 (12)0.31126 (7)0.0289 (4)
O90.08454 (10)−0.00244 (14)0.38154 (7)0.0345 (4)
O100.38760 (11)0.40517 (13)0.26800 (8)0.0368 (5)
H100.41590.46270.26120.055*
O110.07893 (9)0.13556 (12)0.21061 (6)0.0223 (4)
O12−0.02891 (10)0.04463 (13)0.24848 (7)0.0302 (4)
O130.13692 (10)0.32770 (12)0.18371 (7)0.0263 (4)
O140.40080 (10)0.17646 (13)0.11225 (7)0.0318 (4)
O150.10756 (10)−0.25362 (13)0.22829 (8)0.0368 (5)
H150.0815−0.31210.23620.055*
O160.16996 (10)−0.06143 (12)0.03306 (6)0.0237 (4)
O170.27877 (10)0.02844 (13)−0.00470 (7)0.0311 (4)
O180.10944 (10)−0.25392 (12)0.05812 (7)0.0276 (4)
O19−0.15022 (10)−0.09995 (13)0.13372 (7)0.0312 (4)
O200.14506 (11)0.32841 (13)0.01782 (8)0.0356 (5)
H200.16980.38640.00790.053*
C10.45277 (14)0.16623 (18)0.42108 (9)0.0207 (5)
C20.53456 (15)0.17311 (19)0.39616 (9)0.0234 (5)
H20.55600.24200.38440.028*
C30.58498 (14)0.07853 (19)0.38857 (10)0.0244 (6)
C40.55564 (15)−0.0224 (2)0.40567 (10)0.0266 (6)
H40.5914−0.08590.40090.032*
C50.47303 (14)−0.03036 (19)0.43007 (9)0.0211 (5)
C60.43561 (15)−0.13227 (19)0.44780 (9)0.0237 (5)
H60.4687−0.19810.44370.028*
C70.35488 (15)−0.13599 (18)0.47000 (9)0.0222 (5)
C80.30436 (15)−0.03491 (18)0.47759 (9)0.0221 (5)
C90.42242 (14)0.06384 (18)0.43726 (9)0.0196 (5)
C100.43098 (16)0.35850 (18)0.42034 (11)0.0313 (6)
H10A0.48970.36990.44230.047*
H10B0.38700.41320.43110.047*
H10C0.43920.36590.38030.047*
C110.69700 (16)0.1788 (2)0.34201 (11)0.0332 (6)
H11A0.64950.20720.31450.050*
H11B0.75290.16520.32360.050*
H11C0.70950.23240.37220.050*
C120.30893 (15)−0.23834 (18)0.48782 (10)0.0265 (6)
H12A0.2987−0.23370.52810.032*
H12B0.2489−0.24670.46600.032*
C130.29574 (15)−0.09025 (19)0.32277 (9)0.0215 (5)
C140.21541 (14)−0.09679 (19)0.34822 (9)0.0229 (5)
H140.1940−0.16580.35980.027*
C150.16535 (15)−0.00206 (19)0.35712 (9)0.0242 (5)
C160.19569 (15)0.09855 (19)0.34029 (9)0.0251 (5)
H160.16070.16240.34570.030*
C170.27796 (14)0.10636 (18)0.31530 (9)0.0207 (5)
C180.31568 (15)0.20840 (18)0.29729 (9)0.0229 (5)
H180.28320.27450.30190.027*
C190.39549 (14)0.21186 (18)0.27420 (9)0.0217 (5)
C200.44543 (15)0.11029 (18)0.26644 (9)0.0221 (5)
C210.32695 (14)0.01213 (18)0.30696 (9)0.0199 (5)
C220.31769 (17)−0.28333 (18)0.32396 (11)0.0304 (6)
H22A0.3139−0.29000.36460.046*
H22B0.3601−0.33840.31170.046*
H22C0.2571−0.29490.30430.046*
C230.05554 (16)−0.1015 (2)0.40576 (10)0.0319 (6)
H23A0.0453−0.15720.37640.048*
H23B−0.0014−0.08860.42320.048*
H23C0.1027−0.12680.43430.048*
C240.44016 (15)0.31340 (18)0.25490 (10)0.0268 (6)
H24A0.50260.31980.27380.032*
H24B0.44470.30990.21380.032*
C250.19106 (14)0.24339 (18)0.17149 (9)0.0203 (5)
C260.27178 (14)0.25041 (18)0.14697 (9)0.0222 (5)
H260.29380.31990.13660.027*
C270.32196 (14)0.15630 (19)0.13717 (9)0.0224 (5)
C280.29236 (15)0.05458 (19)0.15189 (9)0.0241 (5)
H280.3272−0.00880.14510.029*
C290.20983 (14)0.04547 (18)0.17709 (9)0.0192 (5)
C300.17217 (15)−0.05651 (19)0.19477 (9)0.0220 (5)
H300.2044−0.12250.18940.026*
C310.09317 (15)−0.06079 (18)0.21847 (9)0.0205 (5)
C320.04357 (15)0.03915 (18)0.22739 (9)0.0216 (5)
C330.16038 (14)0.13937 (18)0.18639 (9)0.0185 (5)
C340.17076 (17)0.43486 (18)0.17191 (11)0.0335 (6)
H34A0.22980.44640.19350.050*
H34B0.12720.49020.18250.050*
H34C0.17840.44100.13170.050*
C350.45447 (15)0.0838 (2)0.09976 (11)0.0338 (6)
H35A0.47540.04600.13470.051*
H35B0.50750.10800.08080.051*
H35C0.41740.03370.07520.051*
C360.05020 (15)−0.16391 (18)0.23784 (10)0.0238 (5)
H36A0.0415−0.15850.27840.029*
H36B−0.0104−0.17460.21700.029*
C370.05696 (15)−0.16841 (19)0.07157 (9)0.0212 (5)
C38−0.02323 (14)−0.17498 (18)0.09693 (9)0.0228 (5)
H38−0.0458−0.24450.10700.027*
C39−0.07202 (15)−0.08039 (19)0.10811 (9)0.0234 (5)
C40−0.04122 (14)0.02177 (19)0.09371 (9)0.0230 (5)
H40−0.07490.08570.10110.028*
C410.04095 (15)0.02945 (18)0.06786 (9)0.0209 (5)
C420.07907 (15)0.13177 (18)0.05071 (9)0.0217 (5)
H420.04790.19810.05710.026*
C430.15768 (15)0.13529 (18)0.02582 (9)0.0220 (5)
C440.20614 (15)0.03467 (18)0.01684 (9)0.0226 (5)
C450.08888 (14)−0.06456 (18)0.05764 (9)0.0189 (5)
C460.07568 (17)−0.36016 (19)0.07114 (11)0.0337 (6)
H46A0.0718−0.36610.11180.051*
H46B0.1173−0.41630.05900.051*
H46C0.0149−0.37070.05160.051*
C47−0.20234 (15)−0.0070 (2)0.14792 (10)0.0321 (6)
H47A−0.16430.04100.17320.048*
H47B−0.2555−0.03120.16670.048*
H47C−0.22300.03320.11360.048*
C480.19980 (15)0.23813 (18)0.00552 (10)0.0250 (5)
H48A0.26210.24720.02430.030*
H48B0.20440.2336−0.03550.030*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0190 (8)0.0156 (8)0.0336 (9)−0.0001 (7)0.0122 (7)0.0015 (7)
O20.0240 (9)0.0185 (9)0.0475 (11)0.0006 (7)0.0170 (8)0.0021 (8)
O30.0263 (9)0.0137 (9)0.0479 (11)0.0007 (7)0.0169 (8)0.0038 (8)
O40.0277 (9)0.0263 (10)0.0566 (12)0.0021 (8)0.0237 (9)0.0079 (9)
O50.0302 (10)0.0146 (9)0.0670 (13)0.0002 (7)0.0210 (9)0.0051 (9)
O60.0210 (8)0.0162 (9)0.0339 (9)−0.0007 (7)0.0106 (7)0.0017 (7)
O70.0260 (9)0.0186 (9)0.0488 (11)−0.0012 (7)0.0178 (8)0.0042 (8)
O80.0275 (9)0.0134 (9)0.0483 (11)−0.0004 (7)0.0169 (8)0.0031 (8)
O90.0260 (9)0.0300 (10)0.0502 (11)0.0032 (8)0.0202 (8)0.0090 (8)
O100.0354 (10)0.0147 (9)0.0635 (12)0.0001 (8)0.0221 (9)0.0041 (9)
O110.0204 (8)0.0139 (8)0.0344 (9)0.0001 (7)0.0122 (7)0.0020 (7)
O120.0277 (9)0.0187 (9)0.0472 (11)−0.0012 (7)0.0203 (8)0.0012 (8)
O130.0247 (8)0.0108 (8)0.0455 (10)0.0016 (7)0.0145 (8)0.0046 (7)
O140.0248 (9)0.0214 (9)0.0524 (11)0.0009 (7)0.0219 (8)0.0009 (8)
O150.0314 (9)0.0149 (9)0.0673 (12)−0.0003 (8)0.0214 (9)0.0065 (9)
O160.0238 (8)0.0149 (8)0.0340 (9)0.0000 (7)0.0124 (7)0.0035 (7)
O170.0298 (9)0.0193 (9)0.0473 (11)0.0009 (8)0.0207 (8)0.0030 (8)
O180.0274 (9)0.0120 (8)0.0460 (11)0.0019 (7)0.0172 (8)0.0044 (7)
O190.0244 (9)0.0218 (9)0.0505 (11)0.0009 (7)0.0203 (8)−0.0017 (8)
O200.0344 (10)0.0144 (9)0.0614 (12)0.0007 (8)0.0230 (9)0.0052 (9)
C10.0206 (12)0.0180 (12)0.0241 (13)0.0029 (10)0.0052 (10)0.0010 (10)
C20.0237 (12)0.0186 (13)0.0290 (13)−0.0028 (10)0.0079 (10)0.0026 (10)
C30.0183 (12)0.0239 (13)0.0325 (14)0.0020 (10)0.0107 (10)0.0012 (11)
C40.0231 (12)0.0195 (13)0.0380 (15)0.0029 (10)0.0084 (11)−0.0001 (11)
C50.0199 (12)0.0189 (12)0.0245 (13)−0.0007 (10)0.0028 (10)0.0010 (10)
C60.0250 (13)0.0148 (12)0.0316 (14)0.0027 (10)0.0037 (11)−0.0012 (10)
C70.0223 (12)0.0178 (12)0.0265 (13)−0.0002 (10)0.0025 (10)0.0013 (10)
C80.0231 (12)0.0158 (12)0.0279 (13)−0.0038 (10)0.0055 (10)−0.0009 (10)
C90.0160 (11)0.0193 (13)0.0239 (13)0.0009 (10)0.0037 (10)0.0002 (10)
C100.0361 (14)0.0123 (12)0.0479 (16)−0.0015 (11)0.0165 (12)0.0011 (11)
C110.0271 (13)0.0309 (15)0.0439 (16)−0.0025 (11)0.0160 (12)0.0065 (12)
C120.0248 (12)0.0164 (12)0.0391 (15)0.0008 (10)0.0074 (11)0.0007 (11)
C130.0225 (12)0.0175 (12)0.0249 (13)0.0026 (10)0.0043 (10)0.0014 (10)
C140.0239 (12)0.0183 (12)0.0272 (13)−0.0035 (10)0.0058 (10)0.0023 (10)
C150.0185 (12)0.0279 (14)0.0271 (13)−0.0002 (10)0.0075 (10)0.0003 (10)
C160.0251 (12)0.0186 (13)0.0325 (14)0.0063 (10)0.0083 (11)0.0012 (10)
C170.0198 (11)0.0173 (12)0.0250 (13)0.0016 (10)0.0025 (10)0.0001 (10)
C180.0272 (12)0.0136 (12)0.0280 (13)0.0008 (10)0.0033 (10)0.0006 (10)
C190.0231 (12)0.0163 (12)0.0260 (13)−0.0014 (10)0.0033 (10)0.0017 (10)
C200.0210 (12)0.0178 (12)0.0279 (13)−0.0031 (10)0.0040 (10)0.0015 (10)
C210.0176 (11)0.0194 (13)0.0231 (13)−0.0002 (10)0.0034 (10)−0.0001 (10)
C220.0359 (14)0.0125 (12)0.0450 (16)−0.0024 (11)0.0164 (12)0.0026 (11)
C230.0259 (13)0.0317 (15)0.0402 (16)−0.0037 (11)0.0154 (12)0.0022 (12)
C240.0260 (13)0.0168 (12)0.0387 (15)0.0015 (10)0.0093 (11)0.0013 (11)
C250.0221 (11)0.0157 (12)0.0234 (12)0.0021 (10)0.0039 (10)0.0007 (10)
C260.0212 (11)0.0157 (12)0.0305 (13)−0.0013 (10)0.0071 (10)0.0013 (10)
C270.0179 (11)0.0214 (12)0.0287 (13)−0.0003 (10)0.0072 (10)0.0006 (10)
C280.0225 (12)0.0181 (13)0.0326 (14)0.0030 (10)0.0075 (11)−0.0003 (10)
C290.0191 (12)0.0166 (12)0.0222 (12)−0.0006 (10)0.0045 (10)0.0018 (10)
C300.0241 (12)0.0146 (12)0.0275 (13)0.0021 (10)0.0045 (10)−0.0002 (10)
C310.0226 (12)0.0153 (12)0.0238 (12)−0.0040 (10)0.0038 (10)0.0010 (10)
C320.0220 (12)0.0179 (12)0.0257 (13)−0.0036 (10)0.0071 (10)0.0011 (10)
C330.0150 (11)0.0178 (12)0.0229 (13)−0.0017 (9)0.0032 (9)0.0013 (10)
C340.0382 (15)0.0110 (12)0.0544 (17)0.0029 (11)0.0217 (13)0.0051 (11)
C350.0239 (13)0.0257 (14)0.0547 (18)0.0057 (11)0.0205 (12)−0.0023 (12)
C360.0224 (12)0.0152 (12)0.0349 (14)−0.0005 (10)0.0079 (11)0.0027 (10)
C370.0209 (12)0.0169 (12)0.0261 (13)0.0018 (10)0.0042 (10)0.0022 (10)
C380.0229 (12)0.0152 (12)0.0313 (14)−0.0036 (10)0.0080 (10)−0.0003 (10)
C390.0195 (12)0.0211 (13)0.0303 (14)0.0002 (10)0.0063 (10)−0.0015 (10)
C400.0226 (12)0.0167 (12)0.0304 (14)0.0040 (10)0.0070 (10)−0.0028 (10)
C410.0234 (12)0.0172 (12)0.0222 (12)0.0001 (10)0.0036 (10)0.0012 (10)
C420.0233 (12)0.0154 (12)0.0268 (13)0.0039 (10)0.0033 (10)−0.0016 (10)
C430.0234 (12)0.0183 (13)0.0247 (13)0.0015 (10)0.0041 (10)0.0013 (10)
C440.0239 (12)0.0167 (12)0.0280 (13)−0.0018 (10)0.0063 (10)0.0019 (10)
C450.0157 (11)0.0193 (12)0.0226 (12)0.0001 (9)0.0074 (9)0.0015 (10)
C460.0400 (15)0.0125 (12)0.0517 (17)0.0016 (11)0.0212 (13)0.0049 (11)
C470.0215 (12)0.0272 (14)0.0497 (17)0.0056 (11)0.0158 (12)−0.0038 (12)
C480.0275 (13)0.0165 (12)0.0326 (14)0.0001 (10)0.0113 (11)0.0024 (10)

Geometric parameters (Å, °)

O1—C81.361 (3)C14—H140.9500
O1—C91.379 (2)C15—C161.380 (3)
O2—C81.216 (2)C16—C171.398 (3)
O3—C11.353 (3)C16—H160.9500
O3—C101.431 (3)C17—C211.382 (3)
O4—C31.371 (2)C17—C181.446 (3)
O4—C111.418 (3)C18—C191.340 (3)
O5—C121.407 (3)C18—H180.9500
O5—H50.8400C19—C201.463 (3)
O6—C201.363 (3)C19—C241.496 (3)
O6—C211.379 (2)C22—H22A0.9800
O7—C201.216 (2)C22—H22B0.9800
O8—C131.360 (3)C22—H22C0.9800
O8—C221.435 (2)C23—H23A0.9800
O9—C151.368 (2)C23—H23B0.9800
O9—C231.423 (3)C23—H23C0.9800
O10—C241.413 (3)C24—H24A0.9900
O10—H100.8400C24—H24B0.9900
O11—C321.363 (2)C25—C261.371 (3)
O11—C331.375 (2)C25—C331.405 (3)
O12—C321.220 (2)C26—C271.397 (3)
O13—C251.350 (2)C26—H260.9500
O13—C341.438 (3)C27—C281.373 (3)
O14—C271.371 (2)C28—C291.405 (3)
O14—C351.427 (3)C28—H280.9500
O15—C361.414 (3)C29—C331.387 (3)
O15—H150.8400C29—C301.442 (3)
O16—C441.360 (3)C30—C311.337 (3)
O16—C451.375 (2)C30—H300.9500
O17—C441.227 (2)C31—C321.448 (3)
O18—C371.354 (3)C31—C361.501 (3)
O18—C461.434 (3)C34—H34A0.9800
O19—C391.370 (2)C34—H34B0.9800
O19—C471.428 (3)C34—H34C0.9800
O20—C481.412 (3)C35—H35A0.9800
O20—H200.8400C35—H35B0.9800
C1—C21.390 (3)C35—H35C0.9800
C1—C91.395 (3)C36—H36A0.9900
C2—C31.394 (3)C36—H36B0.9900
C2—H20.9500C37—C381.374 (3)
C3—C41.380 (3)C37—C451.404 (3)
C4—C51.396 (3)C38—C391.399 (3)
C4—H40.9500C38—H380.9500
C5—C91.390 (3)C39—C401.382 (3)
C5—C61.440 (3)C40—C411.407 (3)
C6—C71.342 (3)C40—H400.9500
C6—H60.9500C41—C451.381 (3)
C7—C81.461 (3)C41—C421.445 (3)
C7—C121.501 (3)C42—C431.346 (3)
C10—H10A0.9800C42—H420.9500
C10—H10B0.9800C43—C441.447 (3)
C10—H10C0.9800C43—C481.501 (3)
C11—H11A0.9800C46—H46A0.9800
C11—H11B0.9800C46—H46B0.9800
C11—H11C0.9800C46—H46C0.9800
C12—H12A0.9900C47—H47A0.9800
C12—H12B0.9900C47—H47B0.9800
C13—C141.377 (3)C47—H47C0.9800
C13—C211.396 (3)C48—H48A0.9900
C14—C151.398 (3)C48—H48B0.9900
C8—O1—C9121.02 (17)H23A—C23—H23C109.5
C1—O3—C10116.84 (16)H23B—C23—H23C109.5
C3—O4—C11118.93 (18)O10—C24—C19109.10 (17)
C12—O5—H5109.5O10—C24—H24A109.9
C20—O6—C21121.18 (17)C19—C24—H24A109.9
C13—O8—C22116.95 (17)O10—C24—H24B109.9
C15—O9—C23118.58 (18)C19—C24—H24B109.9
C24—O10—H10109.5H24A—C24—H24B108.3
C32—O11—C33121.44 (17)O13—C25—C26126.4 (2)
C25—O13—C34115.63 (16)O13—C25—C33115.32 (18)
C27—O14—C35116.87 (17)C26—C25—C33118.3 (2)
C36—O15—H15109.5C25—C26—C27120.6 (2)
C44—O16—C45121.41 (17)C25—C26—H26119.7
C37—O18—C46115.62 (16)C27—C26—H26119.7
C39—O19—C47117.11 (17)O14—C27—C28125.0 (2)
C48—O20—H20109.5O14—C27—C26113.80 (19)
O3—C1—C2125.7 (2)C28—C27—C26121.25 (19)
O3—C1—C9115.42 (18)C27—C28—C29119.1 (2)
C2—C1—C9118.9 (2)C27—C28—H28120.5
C1—C2—C3119.7 (2)C29—C28—H28120.5
C1—C2—H2120.2C33—C29—C28119.2 (2)
C3—C2—H2120.2C33—C29—C30116.64 (19)
O4—C3—C4116.0 (2)C28—C29—C30124.2 (2)
O4—C3—C2122.7 (2)C31—C30—C29121.9 (2)
C4—C3—C2121.3 (2)C31—C30—H30119.1
C3—C4—C5119.5 (2)C29—C30—H30119.1
C3—C4—H4120.3C30—C31—C32119.8 (2)
C5—C4—H4120.3C30—C31—C36124.6 (2)
C9—C5—C4119.2 (2)C32—C31—C36115.61 (18)
C9—C5—C6117.25 (19)O12—C32—O11116.3 (2)
C4—C5—C6123.5 (2)O12—C32—C31125.2 (2)
C7—C6—C5121.3 (2)O11—C32—C31118.46 (18)
C7—C6—H6119.4O11—C33—C29121.81 (19)
C5—C6—H6119.4O11—C33—C25116.60 (19)
C6—C7—C8119.8 (2)C29—C33—C25121.59 (19)
C6—C7—C12125.1 (2)O13—C34—H34A109.5
C8—C7—C12115.05 (18)O13—C34—H34B109.5
O2—C8—O1116.6 (2)H34A—C34—H34B109.5
O2—C8—C7124.7 (2)O13—C34—H34C109.5
O1—C8—C7118.68 (18)H34A—C34—H34C109.5
O1—C9—C5121.96 (19)H34B—C34—H34C109.5
O1—C9—C1116.60 (19)O14—C35—H35A109.5
C5—C9—C1121.44 (19)O14—C35—H35B109.5
O3—C10—H10A109.5H35A—C35—H35B109.5
O3—C10—H10B109.5O14—C35—H35C109.5
H10A—C10—H10B109.5H35A—C35—H35C109.5
O3—C10—H10C109.5H35B—C35—H35C109.5
H10A—C10—H10C109.5O15—C36—C31109.18 (17)
H10B—C10—H10C109.5O15—C36—H36A109.8
O4—C11—H11A109.5C31—C36—H36A109.8
O4—C11—H11B109.5O15—C36—H36B109.8
H11A—C11—H11B109.5C31—C36—H36B109.8
O4—C11—H11C109.5H36A—C36—H36B108.3
H11A—C11—H11C109.5O18—C37—C38126.0 (2)
H11B—C11—H11C109.5O18—C37—C45115.65 (18)
O5—C12—C7109.23 (17)C38—C37—C45118.3 (2)
O5—C12—H12A109.8C37—C38—C39120.7 (2)
C7—C12—H12A109.8C37—C38—H38119.7
O5—C12—H12B109.8C39—C38—H38119.7
C7—C12—H12B109.8O19—C39—C40125.1 (2)
H12A—C12—H12B108.3O19—C39—C38113.91 (19)
O8—C13—C14125.7 (2)C40—C39—C38121.0 (2)
O8—C13—C21115.18 (18)C39—C40—C41118.8 (2)
C14—C13—C21119.1 (2)C39—C40—H40120.6
C13—C14—C15120.1 (2)C41—C40—H40120.6
C13—C14—H14119.9C45—C41—C40119.5 (2)
C15—C14—H14119.9C45—C41—C42117.00 (19)
O9—C15—C16116.2 (2)C40—C41—C42123.5 (2)
O9—C15—C14123.4 (2)C43—C42—C41121.5 (2)
C16—C15—C14120.4 (2)C43—C42—H42119.3
C15—C16—C17119.9 (2)C41—C42—H42119.3
C15—C16—H16120.0C42—C43—C44119.4 (2)
C17—C16—H16120.0C42—C43—C48124.3 (2)
C21—C17—C16119.1 (2)C44—C43—C48116.22 (18)
C21—C17—C18117.25 (19)O17—C44—O16116.2 (2)
C16—C17—C18123.7 (2)O17—C44—C43124.9 (2)
C19—C18—C17121.5 (2)O16—C44—C43118.83 (18)
C19—C18—H18119.3O16—C45—C41121.82 (19)
C17—C18—H18119.3O16—C45—C37116.53 (19)
C18—C19—C20119.5 (2)C41—C45—C37121.6 (2)
C18—C19—C24125.2 (2)O18—C46—H46A109.5
C20—C19—C24115.25 (18)O18—C46—H46B109.5
O7—C20—O6116.7 (2)H46A—C46—H46B109.5
O7—C20—C19124.6 (2)O18—C46—H46C109.5
O6—C20—C19118.63 (19)H46A—C46—H46C109.5
O6—C21—C17121.93 (19)H46B—C46—H46C109.5
O6—C21—C13116.71 (19)O19—C47—H47A109.5
C17—C21—C13121.4 (2)O19—C47—H47B109.5
O8—C22—H22A109.5H47A—C47—H47B109.5
O8—C22—H22B109.5O19—C47—H47C109.5
H22A—C22—H22B109.5H47A—C47—H47C109.5
O8—C22—H22C109.5H47B—C47—H47C109.5
H22A—C22—H22C109.5O20—C48—C43109.20 (16)
H22B—C22—H22C109.5O20—C48—H48A109.8
O9—C23—H23A109.5C43—C48—H48A109.8
O9—C23—H23B109.5O20—C48—H48B109.8
H23A—C23—H23B109.5C43—C48—H48B109.8
O9—C23—H23C109.5H48A—C48—H48B108.3
C10—O3—C1—C2−6.8 (3)C34—O13—C25—C26−3.1 (3)
C10—O3—C1—C9173.8 (2)C34—O13—C25—C33176.2 (2)
O3—C1—C2—C3179.7 (2)O13—C25—C26—C27179.2 (2)
C9—C1—C2—C3−0.9 (3)C33—C25—C26—C270.0 (3)
C11—O4—C3—C4174.6 (2)C35—O14—C27—C281.5 (3)
C11—O4—C3—C2−6.6 (3)C35—O14—C27—C26−178.6 (2)
C1—C2—C3—O4−179.2 (2)C25—C26—C27—O14179.78 (19)
C1—C2—C3—C4−0.4 (4)C25—C26—C27—C28−0.3 (3)
O4—C3—C4—C5−179.9 (2)O14—C27—C28—C29−179.8 (2)
C2—C3—C4—C51.2 (4)C26—C27—C28—C290.2 (3)
C3—C4—C5—C9−0.7 (3)C27—C28—C29—C330.1 (3)
C3—C4—C5—C6178.3 (2)C27—C28—C29—C30−179.5 (2)
C9—C5—C6—C70.4 (3)C33—C29—C30—C310.6 (3)
C4—C5—C6—C7−178.6 (2)C28—C29—C30—C31−179.8 (2)
C5—C6—C7—C8−1.3 (3)C29—C30—C31—C32−0.6 (3)
C5—C6—C7—C12177.8 (2)C29—C30—C31—C36−180.0 (2)
C9—O1—C8—O2−179.01 (19)C33—O11—C32—O12179.87 (19)
C9—O1—C8—C70.9 (3)C33—O11—C32—C31−0.9 (3)
C6—C7—C8—O2−179.4 (2)C30—C31—C32—O12179.9 (2)
C12—C7—C8—O21.4 (3)C36—C31—C32—O12−0.7 (3)
C6—C7—C8—O10.7 (3)C30—C31—C32—O110.7 (3)
C12—C7—C8—O1−178.54 (19)C36—C31—C32—O11−179.87 (19)
C8—O1—C9—C5−1.8 (3)C32—O11—C33—C291.0 (3)
C8—O1—C9—C1178.91 (19)C32—O11—C33—C25−179.04 (19)
C4—C5—C9—O1−179.8 (2)C28—C29—C33—O11179.65 (19)
C6—C5—C9—O11.1 (3)C30—C29—C33—O11−0.8 (3)
C4—C5—C9—C1−0.6 (3)C28—C29—C33—C25−0.3 (3)
C6—C5—C9—C1−179.6 (2)C30—C29—C33—C25179.2 (2)
O3—C1—C9—O10.1 (3)O13—C25—C33—O111.0 (3)
C2—C1—C9—O1−179.35 (19)C26—C25—C33—O11−179.67 (19)
O3—C1—C9—C5−179.2 (2)O13—C25—C33—C29−179.0 (2)
C2—C1—C9—C51.4 (3)C26—C25—C33—C290.3 (3)
C6—C7—C12—O51.1 (3)C30—C31—C36—O151.5 (3)
C8—C7—C12—O5−179.77 (19)C32—C31—C36—O15−177.92 (19)
C22—O8—C13—C143.7 (3)C46—O18—C37—C381.2 (3)
C22—O8—C13—C21−176.6 (2)C46—O18—C37—C45−178.6 (2)
O8—C13—C14—C15−179.2 (2)O18—C37—C38—C39−179.2 (2)
C21—C13—C14—C151.1 (3)C45—C37—C38—C390.5 (3)
C23—O9—C15—C16−172.5 (2)C47—O19—C39—C40−1.8 (3)
C23—O9—C15—C148.5 (3)C47—O19—C39—C38178.3 (2)
C13—C14—C15—O9179.2 (2)C37—C38—C39—O19−179.7 (2)
C13—C14—C15—C160.3 (4)C37—C38—C39—C400.4 (4)
O9—C15—C16—C17179.6 (2)O19—C39—C40—C41179.6 (2)
C14—C15—C16—C17−1.4 (4)C38—C39—C40—C41−0.5 (3)
C15—C16—C17—C211.1 (3)C39—C40—C41—C45−0.2 (3)
C15—C16—C17—C18−178.9 (2)C39—C40—C41—C42179.5 (2)
C21—C17—C18—C19−1.0 (3)C45—C41—C42—C430.1 (3)
C16—C17—C18—C19179.1 (2)C40—C41—C42—C43−179.6 (2)
C17—C18—C19—C200.6 (3)C41—C42—C43—C44−1.1 (3)
C17—C18—C19—C24−179.4 (2)C41—C42—C43—C48178.2 (2)
C21—O6—C20—O7178.95 (19)C45—O16—C44—O17−179.98 (19)
C21—O6—C20—C19−1.2 (3)C45—O16—C44—C430.0 (3)
C18—C19—C20—O7−179.7 (2)C42—C43—C44—O17−179.0 (2)
C24—C19—C20—O70.3 (3)C48—C43—C44—O171.6 (3)
C18—C19—C20—O60.4 (3)C42—C43—C44—O161.1 (3)
C24—C19—C20—O6−179.6 (2)C48—C43—C44—O16−178.3 (2)
C20—O6—C21—C170.8 (3)C44—O16—C45—C41−1.0 (3)
C20—O6—C21—C13−179.22 (19)C44—O16—C45—C37178.65 (19)
C16—C17—C21—O6−179.81 (19)C40—C41—C45—O16−179.30 (19)
C18—C17—C21—O60.2 (3)C42—C41—C45—O161.0 (3)
C16—C17—C21—C130.2 (3)C40—C41—C45—C371.1 (3)
C18—C17—C21—C13−179.7 (2)C42—C41—C45—C37−178.7 (2)
O8—C13—C21—O6−1.0 (3)O18—C37—C45—O16−1.1 (3)
C14—C13—C21—O6178.70 (19)C38—C37—C45—O16179.12 (19)
O8—C13—C21—C17178.9 (2)O18—C37—C45—C41178.5 (2)
C14—C13—C21—C17−1.3 (3)C38—C37—C45—C41−1.2 (3)
C18—C19—C24—O103.5 (3)C42—C43—C48—O201.2 (3)
C20—C19—C24—O10−176.47 (19)C44—C43—C48—O20−179.46 (19)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O20—H20···O2i0.842.002.829 (2)171
O15—H15···O12ii0.841.962.800 (2)175
O10—H10···O7iii0.842.002.838 (2)174
O5—H5···O17iv0.841.962.790 (2)173

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2466).

References

  • Ayer, W. A. & Racok, J. S. (1990). Can. J. Chem.68, 2085–2094.
  • Bruker (1997). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2001). SADABS and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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