Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The crystal structure of scandenin [systematic name: 4-hydroxy-3-(4-hydroxy­phenyl)-5-methoxy-8,8-di­methyl-6-(3-methyl-2-butenyl)-2H,8H-pyrano­[2,3f]­chromen-2-one], C26H26O6, has been determined. The compound crystallizes in the monoclinic space group P21/c with two independent but chemically identical mol­ecules in the asymmetric unit. In both mol­ecules, the coumarin moiety is planar and the angularly fused pyran ring is in a sofa conformation. The crystal structure is stabilized by intra- and intermolecular O—H...O hydrogen bonds, with O...O distances in the range 2.601 (1)–2.699 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003594/rz6045sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003594/rz6045Isup2.hkl
Contains datablock I

CCDC reference: 269854

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.047
  • wR factor = 0.139
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17'
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

4-hydroxy-3-(4-hydroxyphenyl)-5-methoxy-8,8-dimethyl-6-(3-methyl-2-butenyl)- 2H,8H-pyrano[2,3f]chromen-2-one top
Crystal data top
C26H26O6F(000) = 1840
Mr = 434.47Dx = 1.268 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8147 reflections
a = 18.1505 (10) Åθ = 2.4–27.5°
b = 17.3369 (10) ŵ = 0.09 mm1
c = 14.5209 (8) ÅT = 273 K
β = 95.054 (1)°Prism, colorless
V = 4551.6 (4) Å30.20 × 0.15 × 0.10 mm
Z = 8
Data collection top
CCD Area Detector
diffractometer
8015 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 28.0°, θmin = 1.8°
ω scansh = 2323
38617 measured reflectionsk = 2222
10593 independent reflectionsl = 1919
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.139 w = 1/[σ2(Fo2) + (0.0726P)2 + 0.7894P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
10593 reflectionsΔρmax = 0.22 e Å3
604 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0020 (3)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.11515 (6)0.62268 (6)0.52398 (6)0.0534 (3)
O20.14271 (8)0.70919 (6)0.63147 (7)0.0734 (4)
O30.10431 (7)0.45345 (6)0.71891 (7)0.0565 (3)
H30.0934 (12)0.4126 (13)0.6869 (15)0.091 (7)*
O40.08788 (7)0.35288 (6)0.58538 (7)0.0585 (3)
O50.05818 (6)0.44732 (6)0.27818 (6)0.0567 (3)
O60.18421 (8)0.65406 (8)1.06380 (7)0.0721 (4)
H60.1675 (14)0.7000 (16)1.0749 (17)0.117 (9)*
C10.12992 (9)0.64153 (8)0.61627 (9)0.0511 (3)
C20.12737 (8)0.58186 (8)0.68432 (9)0.0444 (3)
C30.11156 (8)0.50822 (8)0.65556 (9)0.0443 (3)
C40.10114 (8)0.48851 (8)0.55832 (9)0.0439 (3)
C50.08841 (8)0.41347 (8)0.52296 (9)0.0464 (3)
C60.07468 (8)0.39882 (8)0.42915 (9)0.0467 (3)
C70.07555 (8)0.46220 (9)0.36919 (9)0.0475 (3)
C80.08872 (8)0.53756 (9)0.39987 (9)0.0482 (3)
C90.10206 (8)0.54846 (8)0.49506 (9)0.0456 (3)
C100.08339 (10)0.59972 (10)0.33208 (10)0.0608 (4)
H100.08350.65090.35130.073*
C110.07841 (10)0.58277 (11)0.24286 (11)0.0654 (4)
H110.07210.62260.19990.078*
C120.08256 (9)0.50144 (10)0.20899 (10)0.0575 (4)
C130.16137 (11)0.48098 (16)0.19369 (16)0.0914 (7)
H13A0.19190.48610.25080.137*
H13B0.17900.51510.14840.137*
H13C0.16340.42870.17210.137*
C140.03029 (11)0.48688 (11)0.12351 (11)0.0675 (5)
H14A0.03260.43350.10640.101*
H14B0.04440.51840.07370.101*
H14C0.01930.49950.13630.101*
C150.06041 (9)0.31852 (9)0.39099 (10)0.0532 (3)
H15A0.04040.28680.43780.064*
H15B0.02370.32120.33830.064*
C160.12919 (9)0.28147 (9)0.36170 (10)0.0538 (3)
H160.15790.31180.32600.065*
C170.15401 (10)0.21117 (10)0.38036 (11)0.0615 (4)
C180.22667 (11)0.18480 (13)0.34972 (16)0.0868 (6)
H18A0.24680.22440.31310.130*
H18B0.21930.13870.31350.130*
H18C0.26040.17440.40300.130*
C190.11498 (16)0.15321 (12)0.43409 (18)0.1027 (8)
H19A0.06790.17340.44750.154*
H19B0.14420.14210.49090.154*
H19C0.10770.10670.39850.154*
C200.15806 (13)0.31311 (12)0.59989 (13)0.0829 (6)
H20A0.17160.29320.54200.124*
H20B0.15380.27130.64250.124*
H20C0.19540.34850.62480.124*
C210.14180 (8)0.60247 (8)0.78394 (9)0.0448 (3)
C220.18806 (9)0.55747 (9)0.84333 (9)0.0506 (3)
H220.21040.51420.82010.061*
C230.20168 (9)0.57525 (9)0.93580 (10)0.0562 (4)
H230.23300.54420.97400.067*
C240.16891 (9)0.63920 (8)0.97171 (9)0.0520 (3)
C250.12248 (10)0.68453 (9)0.91450 (10)0.0560 (4)
H250.09970.72730.93830.067*
C260.10956 (9)0.66659 (9)0.82141 (10)0.0549 (4)
H260.07870.69810.78330.066*
O1'0.38577 (6)0.38011 (6)0.99993 (6)0.0514 (2)
O2'0.36366 (9)0.29298 (7)1.10299 (8)0.0764 (4)
O3'0.41917 (7)0.54511 (6)1.20067 (6)0.0541 (3)
H3'0.4324 (11)0.5853 (12)1.1708 (14)0.079 (6)*
O4'0.43174 (6)0.64669 (6)1.07120 (7)0.0537 (3)
O5'0.42114 (7)0.55930 (6)0.76174 (6)0.0587 (3)
O6'0.32971 (9)0.34186 (7)1.52463 (7)0.0718 (4)
H6'0.3449 (13)0.2949 (15)1.5365 (16)0.101 (8)*
C1'0.37781 (9)0.36044 (8)1.09043 (9)0.0511 (3)
C2'0.38764 (8)0.41849 (8)1.16038 (9)0.0443 (3)
C3'0.40486 (8)0.49190 (8)1.13482 (9)0.0429 (3)
C4'0.40782 (7)0.51285 (8)1.03878 (8)0.0418 (3)
C5'0.41994 (8)0.58833 (8)1.00623 (9)0.0434 (3)
C6'0.42299 (8)0.60429 (8)0.91335 (9)0.0441 (3)
C7'0.41332 (8)0.54218 (8)0.85124 (9)0.0456 (3)
C8'0.40107 (8)0.46691 (8)0.87934 (9)0.0454 (3)
C9'0.39795 (8)0.45470 (8)0.97358 (9)0.0432 (3)
C10'0.39634 (10)0.40598 (10)0.81016 (10)0.0587 (4)
H10'0.39370.35460.82810.070*
C11'0.39576 (11)0.42407 (11)0.72170 (10)0.0668 (5)
H11'0.39510.38430.67870.080*
C12'0.39618 (9)0.50520 (10)0.68737 (9)0.0564 (4)
C13'0.31905 (11)0.53031 (16)0.65048 (14)0.0887 (7)
H13D0.28600.52510.69820.133*
H13E0.30210.49850.59880.133*
H13F0.32030.58320.63110.133*
C14'0.45095 (9)0.51608 (11)0.61530 (10)0.0605 (4)
H14D0.45230.56950.59800.091*
H14E0.43600.48550.56180.091*
H14F0.49920.50020.64050.091*
C15'0.43541 (8)0.68449 (8)0.87740 (10)0.0506 (3)
H15D0.45920.71570.92690.061*
H15E0.46840.68170.82840.061*
C16'0.36434 (9)0.72253 (9)0.84093 (10)0.0534 (3)
H16'0.33040.69160.80640.064*
C17'0.34476 (10)0.79471 (9)0.85240 (11)0.0580 (4)
C18'0.27048 (12)0.82374 (13)0.81316 (17)0.0884 (6)
H18D0.24340.78240.78200.133*
H18E0.27720.86460.77010.133*
H18F0.24340.84280.86230.133*
C19'0.39221 (15)0.85272 (11)0.90483 (16)0.0916 (7)
H19D0.44000.83080.92190.137*
H19E0.36960.86750.95950.137*
H19F0.39760.89730.86680.137*
C20'0.36833 (13)0.69534 (12)1.08107 (12)0.0801 (6)
H20D0.35210.71781.02230.120*
H20E0.38170.73551.12490.120*
H20F0.32910.66501.10260.120*
C21'0.37660 (8)0.39738 (8)1.25757 (8)0.0436 (3)
C22'0.33421 (8)0.44446 (8)1.30868 (9)0.0490 (3)
H22'0.31550.49021.28270.059*
C23'0.31894 (10)0.42528 (9)1.39743 (10)0.0558 (4)
H23'0.28940.45741.43000.067*
C24'0.34751 (9)0.35856 (8)1.43754 (9)0.0505 (3)
C25'0.39237 (9)0.31210 (8)1.38936 (10)0.0525 (3)
H25'0.41370.26821.41720.063*
C26'0.40579 (9)0.33069 (8)1.29947 (10)0.0520 (3)
H26'0.43470.29811.26680.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0769 (7)0.0474 (5)0.0347 (5)0.0109 (5)0.0016 (4)0.0022 (4)
O20.1256 (11)0.0487 (6)0.0442 (6)0.0245 (6)0.0022 (6)0.0023 (5)
O30.0879 (8)0.0455 (6)0.0370 (5)0.0087 (5)0.0100 (5)0.0005 (4)
O40.0842 (8)0.0463 (6)0.0449 (5)0.0029 (5)0.0058 (5)0.0014 (4)
O50.0697 (7)0.0649 (7)0.0344 (5)0.0060 (5)0.0019 (4)0.0052 (4)
O60.1163 (11)0.0637 (7)0.0350 (5)0.0143 (7)0.0013 (6)0.0071 (5)
C10.0665 (9)0.0495 (8)0.0364 (7)0.0088 (7)0.0001 (6)0.0002 (6)
C20.0528 (7)0.0465 (7)0.0336 (6)0.0034 (6)0.0026 (5)0.0001 (5)
C30.0515 (7)0.0464 (7)0.0351 (6)0.0017 (6)0.0052 (5)0.0019 (5)
C40.0501 (7)0.0464 (7)0.0352 (6)0.0017 (6)0.0037 (5)0.0016 (5)
C50.0531 (8)0.0470 (7)0.0394 (7)0.0002 (6)0.0057 (6)0.0004 (6)
C60.0493 (7)0.0497 (8)0.0409 (7)0.0008 (6)0.0023 (6)0.0061 (6)
C70.0474 (7)0.0599 (8)0.0347 (6)0.0000 (6)0.0007 (5)0.0047 (6)
C80.0535 (8)0.0553 (8)0.0353 (7)0.0045 (6)0.0008 (6)0.0007 (6)
C90.0511 (7)0.0477 (7)0.0377 (6)0.0039 (6)0.0013 (5)0.0013 (5)
C100.0822 (11)0.0573 (9)0.0412 (7)0.0124 (8)0.0046 (7)0.0039 (7)
C110.0844 (12)0.0694 (10)0.0406 (8)0.0145 (9)0.0045 (7)0.0070 (7)
C120.0607 (9)0.0752 (10)0.0355 (7)0.0022 (8)0.0010 (6)0.0026 (7)
C130.0658 (11)0.130 (2)0.0797 (14)0.0087 (12)0.0131 (10)0.0199 (13)
C140.0799 (11)0.0816 (12)0.0388 (8)0.0012 (9)0.0074 (7)0.0051 (8)
C150.0586 (9)0.0533 (8)0.0470 (8)0.0032 (7)0.0004 (6)0.0094 (6)
C160.0622 (9)0.0533 (8)0.0453 (7)0.0028 (7)0.0020 (6)0.0088 (6)
C170.0734 (10)0.0547 (9)0.0539 (9)0.0028 (8)0.0071 (7)0.0124 (7)
C180.0777 (13)0.0808 (13)0.0983 (15)0.0194 (10)0.0122 (11)0.0274 (12)
C190.149 (2)0.0586 (12)0.1029 (18)0.0013 (13)0.0236 (16)0.0056 (11)
C200.1201 (17)0.0736 (12)0.0521 (10)0.0323 (12)0.0078 (10)0.0004 (9)
C210.0558 (8)0.0438 (7)0.0349 (6)0.0068 (6)0.0044 (6)0.0010 (5)
C220.0640 (9)0.0497 (8)0.0386 (7)0.0052 (7)0.0069 (6)0.0022 (6)
C230.0749 (10)0.0553 (9)0.0377 (7)0.0086 (7)0.0010 (7)0.0015 (6)
C240.0738 (10)0.0481 (8)0.0341 (6)0.0044 (7)0.0047 (6)0.0028 (6)
C250.0791 (10)0.0437 (7)0.0450 (8)0.0054 (7)0.0040 (7)0.0066 (6)
C260.0716 (10)0.0471 (8)0.0443 (7)0.0034 (7)0.0040 (7)0.0017 (6)
O1'0.0749 (7)0.0473 (5)0.0321 (4)0.0119 (5)0.0054 (4)0.0032 (4)
O2'0.1373 (12)0.0491 (6)0.0444 (6)0.0277 (7)0.0167 (7)0.0048 (5)
O3'0.0843 (8)0.0457 (6)0.0316 (5)0.0123 (5)0.0004 (5)0.0014 (4)
O4'0.0773 (7)0.0442 (5)0.0397 (5)0.0039 (5)0.0048 (5)0.0031 (4)
O5'0.0838 (8)0.0624 (6)0.0303 (5)0.0029 (5)0.0063 (5)0.0047 (4)
O6'0.1240 (11)0.0570 (7)0.0371 (5)0.0082 (7)0.0218 (6)0.0073 (5)
C1'0.0702 (9)0.0482 (8)0.0352 (7)0.0106 (7)0.0061 (6)0.0001 (6)
C2'0.0561 (8)0.0457 (7)0.0308 (6)0.0051 (6)0.0021 (5)0.0006 (5)
C3'0.0519 (7)0.0445 (7)0.0315 (6)0.0029 (6)0.0001 (5)0.0014 (5)
C4'0.0492 (7)0.0453 (7)0.0307 (6)0.0020 (5)0.0016 (5)0.0014 (5)
C5'0.0511 (7)0.0440 (7)0.0345 (6)0.0008 (6)0.0008 (5)0.0002 (5)
C6'0.0496 (7)0.0465 (7)0.0362 (6)0.0036 (6)0.0040 (5)0.0056 (5)
C7'0.0506 (7)0.0559 (8)0.0301 (6)0.0022 (6)0.0031 (5)0.0046 (5)
C8'0.0523 (7)0.0523 (8)0.0312 (6)0.0030 (6)0.0018 (5)0.0014 (5)
C9'0.0500 (7)0.0452 (7)0.0342 (6)0.0036 (6)0.0020 (5)0.0007 (5)
C10'0.0808 (11)0.0595 (9)0.0363 (7)0.0167 (8)0.0077 (7)0.0059 (6)
C11'0.0908 (12)0.0734 (11)0.0366 (7)0.0206 (9)0.0087 (7)0.0106 (7)
C12'0.0625 (9)0.0775 (10)0.0293 (6)0.0015 (8)0.0035 (6)0.0014 (6)
C13'0.0632 (11)0.146 (2)0.0567 (10)0.0136 (12)0.0043 (8)0.0077 (12)
C14'0.0667 (10)0.0770 (11)0.0386 (7)0.0019 (8)0.0096 (7)0.0016 (7)
C15'0.0610 (9)0.0493 (8)0.0420 (7)0.0003 (6)0.0070 (6)0.0080 (6)
C16'0.0647 (9)0.0491 (8)0.0452 (7)0.0022 (7)0.0013 (6)0.0071 (6)
C17'0.0739 (10)0.0513 (8)0.0491 (8)0.0029 (7)0.0071 (7)0.0096 (7)
C18'0.0847 (14)0.0739 (13)0.1051 (17)0.0183 (11)0.0000 (12)0.0182 (12)
C19'0.1300 (19)0.0540 (10)0.0856 (14)0.0010 (11)0.0196 (13)0.0007 (10)
C20'0.1193 (17)0.0696 (11)0.0535 (10)0.0272 (11)0.0193 (10)0.0023 (8)
C21'0.0541 (8)0.0444 (7)0.0320 (6)0.0092 (6)0.0014 (5)0.0006 (5)
C22'0.0582 (8)0.0490 (8)0.0395 (7)0.0028 (6)0.0021 (6)0.0056 (6)
C23'0.0752 (10)0.0521 (8)0.0415 (7)0.0059 (7)0.0121 (7)0.0009 (6)
C24'0.0736 (10)0.0474 (8)0.0306 (6)0.0077 (7)0.0048 (6)0.0002 (5)
C25'0.0762 (10)0.0407 (7)0.0404 (7)0.0007 (7)0.0035 (7)0.0058 (6)
C26'0.0698 (9)0.0451 (7)0.0425 (7)0.0011 (7)0.0130 (6)0.0012 (6)
Geometric parameters (Å, º) top
O1—C91.3677 (17)O1'—C9'1.3721 (16)
O1—C11.3825 (16)O1'—C1'1.3775 (16)
O2—C11.2122 (18)O2'—C1'1.2146 (18)
O3—C31.3366 (16)O3'—C3'1.3376 (16)
O3—H30.86 (2)O3'—H3'0.87 (2)
O4—C51.3881 (17)O4'—C5'1.3871 (16)
O4—C201.447 (2)O4'—C20'1.444 (2)
O5—C71.3561 (16)O5'—C7'1.3527 (15)
O5—C121.4710 (19)O5'—C12'1.4714 (18)
O6—C241.3661 (17)O6'—C24'1.3637 (17)
O6—H60.87 (3)O6'—H6'0.87 (3)
C1—C21.4342 (19)C1'—C2'1.4298 (19)
C2—C31.3659 (19)C2'—C3'1.3694 (19)
C2—C211.4907 (18)C2'—C21'1.4885 (17)
C3—C41.4488 (18)C3'—C4'1.4467 (17)
C4—C91.3883 (19)C4'—C9'1.3839 (18)
C4—C51.4102 (19)C4'—C5'1.4151 (18)
C5—C61.3865 (19)C5'—C6'1.3827 (18)
C6—C71.403 (2)C6'—C7'1.406 (2)
C6—C151.512 (2)C6'—C15'1.5090 (19)
C7—C81.394 (2)C7'—C8'1.391 (2)
C8—C91.3950 (18)C8'—C9'1.3907 (18)
C8—C101.457 (2)C8'—C10'1.455 (2)
C10—C111.324 (2)C10'—C11'1.321 (2)
C10—H100.9300C10'—H10'0.9300
C11—C121.497 (2)C11'—C12'1.493 (2)
C11—H110.9300C11'—H11'0.9300
C12—C131.509 (3)C12'—C14'1.517 (2)
C12—C141.516 (2)C12'—C13'1.518 (2)
C13—H13A0.9600C13'—H13D0.9600
C13—H13B0.9600C13'—H13E0.9600
C13—H13C0.9600C13'—H13F0.9600
C14—H14A0.9600C14'—H14D0.9600
C14—H14B0.9600C14'—H14E0.9600
C14—H14C0.9600C14'—H14F0.9600
C15—C161.499 (2)C15'—C16'1.503 (2)
C15—H15A0.9700C15'—H15D0.9700
C15—H15B0.9700C15'—H15E0.9700
C16—C171.319 (2)C16'—C17'1.315 (2)
C16—H160.9300C16'—H16'0.9300
C17—C191.489 (3)C17'—C19'1.489 (3)
C17—C181.500 (3)C17'—C18'1.503 (3)
C18—H18A0.9600C18'—H18D0.9600
C18—H18B0.9600C18'—H18E0.9600
C18—H18C0.9600C18'—H18F0.9600
C19—H19A0.9600C19'—H19D0.9600
C19—H19B0.9600C19'—H19E0.9600
C19—H19C0.9600C19'—H19F0.9600
C20—H20A0.9600C20'—H20D0.9600
C20—H20B0.9600C20'—H20E0.9600
C20—H20C0.9600C20'—H20F0.9600
C21—C221.389 (2)C21'—C22'1.382 (2)
C21—C261.389 (2)C21'—C26'1.390 (2)
C22—C231.3786 (19)C22'—C23'1.3824 (19)
C22—H220.9300C22'—H22'0.9300
C23—C241.382 (2)C23'—C24'1.376 (2)
C23—H230.9300C23'—H23'0.9300
C24—C251.376 (2)C24'—C25'1.379 (2)
C25—C261.387 (2)C25'—C26'1.3868 (19)
C25—H250.9300C25'—H25'0.9300
C26—H260.9300C26'—H26'0.9300
C9—O1—C1122.25 (11)C9'—O1'—C1'122.17 (11)
C3—O3—H3104.2 (15)C3'—O3'—H3'103.9 (13)
C5—O4—C20113.51 (13)C5'—O4'—C20'114.63 (13)
C7—O5—C12119.09 (12)C7'—O5'—C12'120.92 (12)
C24—O6—H6108.0 (17)C24'—O6'—H6'106.5 (16)
O2—C1—O1115.02 (12)O2'—C1'—O1'115.02 (12)
O2—C1—C2126.15 (13)O2'—C1'—C2'125.87 (13)
O1—C1—C2118.82 (12)O1'—C1'—C2'119.10 (12)
C3—C2—C1118.83 (12)C3'—C2'—C1'118.61 (12)
C3—C2—C21122.35 (12)C3'—C2'—C21'122.58 (12)
C1—C2—C21118.82 (12)C1'—C2'—C21'118.79 (12)
O3—C3—C2118.97 (12)O3'—C3'—C2'118.80 (12)
O3—C3—C4119.40 (12)O3'—C3'—C4'119.64 (12)
C2—C3—C4121.63 (12)C2'—C3'—C4'121.56 (12)
C9—C4—C5117.44 (12)C9'—C4'—C5'117.37 (11)
C9—C4—C3117.39 (12)C9'—C4'—C3'117.58 (12)
C5—C4—C3125.14 (12)C5'—C4'—C3'125.05 (12)
C6—C5—O4119.47 (12)C6'—C5'—O4'120.03 (12)
C6—C5—C4122.43 (13)C6'—C5'—C4'122.12 (12)
O4—C5—C4118.08 (12)O4'—C5'—C4'117.81 (11)
C5—C6—C7117.09 (13)C5'—C6'—C7'117.33 (12)
C5—C6—C15122.60 (13)C5'—C6'—C15'122.81 (13)
C7—C6—C15120.30 (12)C7'—C6'—C15'119.86 (12)
O5—C7—C8120.54 (13)O5'—C7'—C8'121.38 (12)
O5—C7—C6116.20 (13)O5'—C7'—C6'115.51 (12)
C8—C7—C6123.14 (12)C8'—C7'—C6'123.00 (12)
C7—C8—C9116.97 (13)C9'—C8'—C7'116.92 (12)
C7—C8—C10118.55 (13)C9'—C8'—C10'124.32 (13)
C9—C8—C10124.38 (14)C7'—C8'—C10'118.67 (12)
O1—C9—C4120.87 (12)O1'—C9'—C4'120.68 (11)
O1—C9—C8116.23 (12)O1'—C9'—C8'116.06 (12)
C4—C9—C8122.89 (13)C4'—C9'—C8'123.25 (13)
C11—C10—C8119.46 (16)C11'—C10'—C8'119.59 (15)
C11—C10—H10120.3C11'—C10'—H10'120.2
C8—C10—H10120.3C8'—C10'—H10'120.2
C10—C11—C12121.97 (15)C10'—C11'—C12'123.27 (15)
C10—C11—H11119.0C10'—C11'—H11'118.4
C12—C11—H11119.0C12'—C11'—H11'118.4
O5—C12—C11110.45 (12)O5'—C12'—C11'111.46 (11)
O5—C12—C13107.26 (14)O5'—C12'—C14'104.41 (13)
C11—C12—C13110.21 (17)C11'—C12'—C14'111.75 (14)
O5—C12—C14104.41 (13)O5'—C12'—C13'106.91 (15)
C11—C12—C14112.33 (14)C11'—C12'—C13'110.88 (17)
C13—C12—C14111.92 (15)C14'—C12'—C13'111.16 (13)
C12—C13—H13A109.5C12'—C13'—H13D109.5
C12—C13—H13B109.5C12'—C13'—H13E109.5
H13A—C13—H13B109.5H13D—C13'—H13E109.5
C12—C13—H13C109.5C12'—C13'—H13F109.5
H13A—C13—H13C109.5H13D—C13'—H13F109.5
H13B—C13—H13C109.5H13E—C13'—H13F109.5
C12—C14—H14A109.5C12'—C14'—H14D109.5
C12—C14—H14B109.5C12'—C14'—H14E109.5
H14A—C14—H14B109.5H14D—C14'—H14E109.5
C12—C14—H14C109.5C12'—C14'—H14F109.5
H14A—C14—H14C109.5H14D—C14'—H14F109.5
H14B—C14—H14C109.5H14E—C14'—H14F109.5
C16—C15—C6112.25 (13)C16'—C15'—C6'112.12 (12)
C16—C15—H15A109.2C16'—C15'—H15D109.2
C6—C15—H15A109.2C6'—C15'—H15D109.2
C16—C15—H15B109.2C16'—C15'—H15E109.2
C6—C15—H15B109.2C6'—C15'—H15E109.2
H15A—C15—H15B107.9H15D—C15'—H15E107.9
C17—C16—C15128.00 (16)C17'—C16'—C15'127.30 (15)
C17—C16—H16116.0C17'—C16'—H16'116.4
C15—C16—H16116.0C15'—C16'—H16'116.4
C16—C17—C19124.15 (18)C16'—C17'—C19'123.83 (17)
C16—C17—C18120.92 (18)C16'—C17'—C18'120.91 (17)
C19—C17—C18114.91 (18)C19'—C17'—C18'115.25 (17)
C17—C18—H18A109.5C17'—C18'—H18D109.5
C17—C18—H18B109.5C17'—C18'—H18E109.5
H18A—C18—H18B109.5H18D—C18'—H18E109.5
C17—C18—H18C109.5C17'—C18'—H18F109.5
H18A—C18—H18C109.5H18D—C18'—H18F109.5
H18B—C18—H18C109.5H18E—C18'—H18F109.5
C17—C19—H19A109.5C17'—C19'—H19D109.5
C17—C19—H19B109.5C17'—C19'—H19E109.5
H19A—C19—H19B109.5H19D—C19'—H19E109.5
C17—C19—H19C109.5C17'—C19'—H19F109.5
H19A—C19—H19C109.5H19D—C19'—H19F109.5
H19B—C19—H19C109.5H19E—C19'—H19F109.5
O4—C20—H20A109.5O4'—C20'—H20D109.5
O4—C20—H20B109.5O4'—C20'—H20E109.5
H20A—C20—H20B109.5H20D—C20'—H20E109.5
O4—C20—H20C109.5O4'—C20'—H20F109.5
H20A—C20—H20C109.5H20D—C20'—H20F109.5
H20B—C20—H20C109.5H20E—C20'—H20F109.5
C22—C21—C26117.31 (12)C22'—C21'—C26'117.72 (12)
C22—C21—C2120.84 (12)C22'—C21'—C2'119.46 (12)
C26—C21—C2121.85 (13)C26'—C21'—C2'122.80 (13)
C23—C22—C21121.72 (14)C21'—C22'—C23'121.70 (14)
C23—C22—H22119.1C21'—C22'—H22'119.1
C21—C22—H22119.1C23'—C22'—H22'119.1
C22—C23—C24120.05 (14)C24'—C23'—C22'119.85 (14)
C22—C23—H23120.0C24'—C23'—H23'120.1
C24—C23—H23120.0C22'—C23'—H23'120.1
O6—C24—C25122.95 (14)O6'—C24'—C23'117.37 (14)
O6—C24—C23117.62 (14)O6'—C24'—C25'123.04 (14)
C25—C24—C23119.42 (13)C23'—C24'—C25'119.59 (13)
C24—C25—C26120.15 (14)C24'—C25'—C26'120.15 (14)
C24—C25—H25119.9C24'—C25'—H25'119.9
C26—C25—H25119.9C26'—C25'—H25'119.9
C25—C26—C21121.34 (14)C25'—C26'—C21'120.91 (14)
C25—C26—H26119.3C25'—C26'—H26'119.5
C21—C26—H26119.3C21'—C26'—H26'119.5
C9—O1—C1—O2177.79 (14)C9'—O1'—C1'—O2'176.52 (14)
C9—O1—C1—C23.5 (2)C9'—O1'—C1'—C2'4.5 (2)
O2—C1—C2—C3179.51 (17)O2'—C1'—C2'—C3'178.76 (17)
O1—C1—C2—C31.0 (2)O1'—C1'—C2'—C3'0.1 (2)
O2—C1—C2—C210.3 (3)O2'—C1'—C2'—C21'3.0 (3)
O1—C1—C2—C21178.78 (12)O1'—C1'—C2'—C21'178.08 (13)
C1—C2—C3—O3175.61 (13)C1'—C2'—C3'—O3'175.39 (13)
C21—C2—C3—O34.2 (2)C21'—C2'—C3'—O3'6.5 (2)
C1—C2—C3—C43.2 (2)C1'—C2'—C3'—C4'4.6 (2)
C21—C2—C3—C4177.02 (13)C21'—C2'—C3'—C4'173.52 (13)
O3—C3—C4—C9173.87 (13)O3'—C3'—C4'—C9'175.38 (13)
C2—C3—C4—C94.9 (2)C2'—C3'—C4'—C9'4.6 (2)
O3—C3—C4—C54.5 (2)O3'—C3'—C4'—C5'4.7 (2)
C2—C3—C4—C5176.64 (14)C2'—C3'—C4'—C5'175.26 (14)
C20—O4—C5—C685.63 (17)C20'—O4'—C5'—C6'80.65 (17)
C20—O4—C5—C496.00 (16)C20'—O4'—C5'—C4'101.76 (15)
C9—C4—C5—C62.2 (2)C9'—C4'—C5'—C6'0.9 (2)
C3—C4—C5—C6176.26 (13)C3'—C4'—C5'—C6'179.23 (13)
C9—C4—C5—O4179.54 (13)C9'—C4'—C5'—O4'178.42 (12)
C3—C4—C5—O42.1 (2)C3'—C4'—C5'—O4'1.7 (2)
O4—C5—C6—C7179.71 (13)O4'—C5'—C6'—C7'177.66 (12)
C4—C5—C6—C71.4 (2)C4'—C5'—C6'—C7'0.2 (2)
O4—C5—C6—C151.2 (2)O4'—C5'—C6'—C15'2.9 (2)
C4—C5—C6—C15179.52 (13)C4'—C5'—C6'—C15'179.63 (13)
C12—O5—C7—C825.4 (2)C12'—O5'—C7'—C8'17.9 (2)
C12—O5—C7—C6158.46 (13)C12'—O5'—C7'—C6'165.89 (13)
C5—C6—C7—O5176.64 (12)C5'—C6'—C7'—O5'176.16 (12)
C15—C6—C7—O54.3 (2)C15'—C6'—C7'—O5'4.37 (19)
C5—C6—C7—C80.6 (2)C5'—C6'—C7'—C8'0.0 (2)
C15—C6—C7—C8179.68 (14)C15'—C6'—C7'—C8'179.48 (13)
O5—C7—C8—C9176.41 (13)O5'—C7'—C8'—C9'176.48 (13)
C6—C7—C8—C90.5 (2)C6'—C7'—C8'—C9'0.5 (2)
O5—C7—C8—C100.0 (2)O5'—C7'—C8'—C10'0.3 (2)
C6—C7—C8—C10175.89 (14)C6'—C7'—C8'—C10'176.23 (14)
C1—O1—C9—C41.7 (2)C1'—O1'—C9'—C4'4.5 (2)
C1—O1—C9—C8179.32 (13)C1'—O1'—C9'—C8'176.76 (13)
C5—C4—C9—O1179.03 (13)C5'—C4'—C9'—O1'179.84 (12)
C3—C4—C9—O12.4 (2)C3'—C4'—C9'—O1'0.1 (2)
C5—C4—C9—C82.1 (2)C5'—C4'—C9'—C8'1.5 (2)
C3—C4—C9—C8176.44 (13)C3'—C4'—C9'—C8'178.61 (13)
C7—C8—C9—O1179.76 (13)C7'—C8'—C9'—O1'179.95 (12)
C10—C8—C9—O14.1 (2)C10'—C8'—C9'—O1'3.5 (2)
C7—C8—C9—C41.3 (2)C7'—C8'—C9'—C4'1.3 (2)
C10—C8—C9—C4174.87 (15)C10'—C8'—C9'—C4'175.26 (14)
C7—C8—C10—C1111.0 (2)C9'—C8'—C10'—C11'176.27 (16)
C9—C8—C10—C11172.87 (16)C7'—C8'—C10'—C11'7.2 (2)
C8—C10—C11—C123.7 (3)C8'—C10'—C11'—C12'3.0 (3)
C7—O5—C12—C1136.88 (18)C7'—O5'—C12'—C11'25.7 (2)
C7—O5—C12—C1383.24 (18)C7'—O5'—C12'—C14'146.46 (14)
C7—O5—C12—C14157.85 (13)C7'—O5'—C12'—C13'95.66 (17)
C10—C11—C12—O526.2 (2)C10'—C11'—C12'—O5'18.4 (2)
C10—C11—C12—C1392.1 (2)C10'—C11'—C12'—C14'134.79 (18)
C10—C11—C12—C14142.34 (18)C10'—C11'—C12'—C13'100.6 (2)
C5—C6—C15—C1695.25 (17)C5'—C6'—C15'—C16'98.91 (16)
C7—C6—C15—C1683.78 (17)C7'—C6'—C15'—C16'80.53 (16)
C6—C15—C16—C17133.04 (17)C6'—C15'—C16'—C17'138.78 (16)
C15—C16—C17—C191.8 (3)C15'—C16'—C17'—C19'0.6 (3)
C15—C16—C17—C18176.50 (15)C15'—C16'—C17'—C18'178.52 (16)
C3—C2—C21—C2245.3 (2)C3'—C2'—C21'—C22'45.2 (2)
C1—C2—C21—C22134.94 (15)C1'—C2'—C21'—C22'132.93 (15)
C3—C2—C21—C26134.26 (16)C3'—C2'—C21'—C26'136.40 (15)
C1—C2—C21—C2645.5 (2)C1'—C2'—C21'—C26'45.5 (2)
C26—C21—C22—C230.0 (2)C26'—C21'—C22'—C23'2.1 (2)
C2—C21—C22—C23179.53 (14)C2'—C21'—C22'—C23'176.41 (14)
C21—C22—C23—C240.1 (2)C21'—C22'—C23'—C24'1.3 (2)
C22—C23—C24—O6179.88 (15)C22'—C23'—C24'—O6'178.97 (15)
C22—C23—C24—C250.3 (2)C22'—C23'—C24'—C25'1.2 (2)
O6—C24—C25—C26179.61 (16)O6'—C24'—C25'—C26'177.26 (15)
C23—C24—C25—C260.8 (2)C23'—C24'—C25'—C26'3.0 (2)
C24—C25—C26—C211.0 (3)C24'—C25'—C26'—C21'2.2 (2)
C22—C21—C26—C250.6 (2)C22'—C21'—C26'—C25'0.3 (2)
C2—C21—C26—C25178.98 (14)C2'—C21'—C26'—C25'178.12 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O40.86 (2)1.80 (2)2.605 (2)156 (2)
O6—H6···O2i0.87 (3)1.85 (3)2.699 (2)164 (2)
O3—H3···O40.87 (2)1.79 (2)2.601 (1)154 (2)
O6—H6···O2ii0.87 (3)1.82 (3)2.649 (2)158 (2)
C11—H11···O6iii0.932.553.325 (2)141
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y+1/2, z+1/2; (iii) x, y, z1.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds