The crystal structure of scandenin [systematic name: 4-hydroxy-3-(4-hydroxyphenyl)-5-methoxy-8,8-dimethyl-6-(3-methyl-2-butenyl)-2
H,8
H-pyrano[2,3
f]chromen-2-one], C
26H
26O
6, has been determined. The compound crystallizes in the monoclinic space group
P2
1/
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
CCDC reference: 269854
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (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
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,8
H-pyrano[2,3f]chromen-2-one
top
Crystal data top
C26H26O6 | F(000) = 1840 |
Mr = 434.47 | Dx = 1.268 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8147 reflections |
a = 18.1505 (10) Å | θ = 2.4–27.5° |
b = 17.3369 (10) Å | µ = 0.09 mm−1 |
c = 14.5209 (8) Å | T = 273 K |
β = 95.054 (1)° | Prism, colorless |
V = 4551.6 (4) Å3 | 0.20 × 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 tube | Rint = 0.021 |
Graphite monochromator | θmax = 28.0°, θmin = 1.8° |
ω scans | h = −23→23 |
38617 measured reflections | k = −22→22 |
10593 independent reflections | l = −19→19 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H 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 reflections | Δρmax = 0.22 e Å−3 |
604 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.11515 (6) | 0.62268 (6) | 0.52398 (6) | 0.0534 (3) | |
O2 | 0.14271 (8) | 0.70919 (6) | 0.63147 (7) | 0.0734 (4) | |
O3 | 0.10431 (7) | 0.45345 (6) | 0.71891 (7) | 0.0565 (3) | |
H3 | 0.0934 (12) | 0.4126 (13) | 0.6869 (15) | 0.091 (7)* | |
O4 | 0.08788 (7) | 0.35288 (6) | 0.58538 (7) | 0.0585 (3) | |
O5 | 0.05818 (6) | 0.44732 (6) | 0.27818 (6) | 0.0567 (3) | |
O6 | 0.18421 (8) | 0.65406 (8) | 1.06380 (7) | 0.0721 (4) | |
H6 | 0.1675 (14) | 0.7000 (16) | 1.0749 (17) | 0.117 (9)* | |
C1 | 0.12992 (9) | 0.64153 (8) | 0.61627 (9) | 0.0511 (3) | |
C2 | 0.12737 (8) | 0.58186 (8) | 0.68432 (9) | 0.0444 (3) | |
C3 | 0.11156 (8) | 0.50822 (8) | 0.65556 (9) | 0.0443 (3) | |
C4 | 0.10114 (8) | 0.48851 (8) | 0.55832 (9) | 0.0439 (3) | |
C5 | 0.08841 (8) | 0.41347 (8) | 0.52296 (9) | 0.0464 (3) | |
C6 | 0.07468 (8) | 0.39882 (8) | 0.42915 (9) | 0.0467 (3) | |
C7 | 0.07555 (8) | 0.46220 (9) | 0.36919 (9) | 0.0475 (3) | |
C8 | 0.08872 (8) | 0.53756 (9) | 0.39987 (9) | 0.0482 (3) | |
C9 | 0.10206 (8) | 0.54846 (8) | 0.49506 (9) | 0.0456 (3) | |
C10 | 0.08339 (10) | 0.59972 (10) | 0.33208 (10) | 0.0608 (4) | |
H10 | 0.0835 | 0.6509 | 0.3513 | 0.073* | |
C11 | 0.07841 (10) | 0.58277 (11) | 0.24286 (11) | 0.0654 (4) | |
H11 | 0.0721 | 0.6226 | 0.1999 | 0.078* | |
C12 | 0.08256 (9) | 0.50144 (10) | 0.20899 (10) | 0.0575 (4) | |
C13 | 0.16137 (11) | 0.48098 (16) | 0.19369 (16) | 0.0914 (7) | |
H13A | 0.1919 | 0.4861 | 0.2508 | 0.137* | |
H13B | 0.1790 | 0.5151 | 0.1484 | 0.137* | |
H13C | 0.1634 | 0.4287 | 0.1721 | 0.137* | |
C14 | 0.03029 (11) | 0.48688 (11) | 0.12351 (11) | 0.0675 (5) | |
H14A | 0.0326 | 0.4335 | 0.1064 | 0.101* | |
H14B | 0.0444 | 0.5184 | 0.0737 | 0.101* | |
H14C | −0.0193 | 0.4995 | 0.1363 | 0.101* | |
C15 | 0.06041 (9) | 0.31852 (9) | 0.39099 (10) | 0.0532 (3) | |
H15A | 0.0404 | 0.2868 | 0.4378 | 0.064* | |
H15B | 0.0237 | 0.3212 | 0.3383 | 0.064* | |
C16 | 0.12919 (9) | 0.28147 (9) | 0.36170 (10) | 0.0538 (3) | |
H16 | 0.1579 | 0.3118 | 0.3260 | 0.065* | |
C17 | 0.15401 (10) | 0.21117 (10) | 0.38036 (11) | 0.0615 (4) | |
C18 | 0.22667 (11) | 0.18480 (13) | 0.34972 (16) | 0.0868 (6) | |
H18A | 0.2468 | 0.2244 | 0.3131 | 0.130* | |
H18B | 0.2193 | 0.1387 | 0.3135 | 0.130* | |
H18C | 0.2604 | 0.1744 | 0.4030 | 0.130* | |
C19 | 0.11498 (16) | 0.15321 (12) | 0.43409 (18) | 0.1027 (8) | |
H19A | 0.0679 | 0.1734 | 0.4475 | 0.154* | |
H19B | 0.1442 | 0.1421 | 0.4909 | 0.154* | |
H19C | 0.1077 | 0.1067 | 0.3985 | 0.154* | |
C20 | 0.15806 (13) | 0.31311 (12) | 0.59989 (13) | 0.0829 (6) | |
H20A | 0.1716 | 0.2932 | 0.5420 | 0.124* | |
H20B | 0.1538 | 0.2713 | 0.6425 | 0.124* | |
H20C | 0.1954 | 0.3485 | 0.6248 | 0.124* | |
C21 | 0.14180 (8) | 0.60247 (8) | 0.78394 (9) | 0.0448 (3) | |
C22 | 0.18806 (9) | 0.55747 (9) | 0.84333 (9) | 0.0506 (3) | |
H22 | 0.2104 | 0.5142 | 0.8201 | 0.061* | |
C23 | 0.20168 (9) | 0.57525 (9) | 0.93580 (10) | 0.0562 (4) | |
H23 | 0.2330 | 0.5442 | 0.9740 | 0.067* | |
C24 | 0.16891 (9) | 0.63920 (8) | 0.97171 (9) | 0.0520 (3) | |
C25 | 0.12248 (10) | 0.68453 (9) | 0.91450 (10) | 0.0560 (4) | |
H25 | 0.0997 | 0.7273 | 0.9383 | 0.067* | |
C26 | 0.10956 (9) | 0.66659 (9) | 0.82141 (10) | 0.0549 (4) | |
H26 | 0.0787 | 0.6981 | 0.7833 | 0.066* | |
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' | 0.3937 | 0.3546 | 0.8281 | 0.070* | |
C11' | 0.39576 (11) | 0.42407 (11) | 0.72170 (10) | 0.0668 (5) | |
H11' | 0.3951 | 0.3843 | 0.6787 | 0.080* | |
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) | |
H13D | 0.2860 | 0.5251 | 0.6982 | 0.133* | |
H13E | 0.3021 | 0.4985 | 0.5988 | 0.133* | |
H13F | 0.3203 | 0.5832 | 0.6311 | 0.133* | |
C14' | 0.45095 (9) | 0.51608 (11) | 0.61530 (10) | 0.0605 (4) | |
H14D | 0.4523 | 0.5695 | 0.5980 | 0.091* | |
H14E | 0.4360 | 0.4855 | 0.5618 | 0.091* | |
H14F | 0.4992 | 0.5002 | 0.6405 | 0.091* | |
C15' | 0.43541 (8) | 0.68449 (8) | 0.87740 (10) | 0.0506 (3) | |
H15D | 0.4592 | 0.7157 | 0.9269 | 0.061* | |
H15E | 0.4684 | 0.6817 | 0.8284 | 0.061* | |
C16' | 0.36434 (9) | 0.72253 (9) | 0.84093 (10) | 0.0534 (3) | |
H16' | 0.3304 | 0.6916 | 0.8064 | 0.064* | |
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) | |
H18D | 0.2434 | 0.7824 | 0.7820 | 0.133* | |
H18E | 0.2772 | 0.8646 | 0.7701 | 0.133* | |
H18F | 0.2434 | 0.8428 | 0.8623 | 0.133* | |
C19' | 0.39221 (15) | 0.85272 (11) | 0.90483 (16) | 0.0916 (7) | |
H19D | 0.4400 | 0.8308 | 0.9219 | 0.137* | |
H19E | 0.3696 | 0.8675 | 0.9595 | 0.137* | |
H19F | 0.3976 | 0.8973 | 0.8668 | 0.137* | |
C20' | 0.36833 (13) | 0.69534 (12) | 1.08107 (12) | 0.0801 (6) | |
H20D | 0.3521 | 0.7178 | 1.0223 | 0.120* | |
H20E | 0.3817 | 0.7355 | 1.1249 | 0.120* | |
H20F | 0.3291 | 0.6650 | 1.1026 | 0.120* | |
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' | 0.3155 | 0.4902 | 1.2827 | 0.059* | |
C23' | 0.31894 (10) | 0.42528 (9) | 1.39743 (10) | 0.0558 (4) | |
H23' | 0.2894 | 0.4574 | 1.4300 | 0.067* | |
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' | 0.4137 | 0.2682 | 1.4172 | 0.063* | |
C26' | 0.40579 (9) | 0.33069 (8) | 1.29947 (10) | 0.0520 (3) | |
H26' | 0.4347 | 0.2981 | 1.2668 | 0.062* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0769 (7) | 0.0474 (5) | 0.0347 (5) | −0.0109 (5) | −0.0016 (4) | 0.0022 (4) |
O2 | 0.1256 (11) | 0.0487 (6) | 0.0442 (6) | −0.0245 (6) | −0.0022 (6) | 0.0023 (5) |
O3 | 0.0879 (8) | 0.0455 (6) | 0.0370 (5) | −0.0087 (5) | 0.0100 (5) | 0.0005 (4) |
O4 | 0.0842 (8) | 0.0463 (6) | 0.0449 (5) | −0.0029 (5) | 0.0058 (5) | 0.0014 (4) |
O5 | 0.0697 (7) | 0.0649 (7) | 0.0344 (5) | −0.0060 (5) | −0.0019 (4) | −0.0052 (4) |
O6 | 0.1163 (11) | 0.0637 (7) | 0.0350 (5) | 0.0143 (7) | −0.0013 (6) | −0.0071 (5) |
C1 | 0.0665 (9) | 0.0495 (8) | 0.0364 (7) | −0.0088 (7) | 0.0001 (6) | −0.0002 (6) |
C2 | 0.0528 (7) | 0.0465 (7) | 0.0336 (6) | −0.0034 (6) | 0.0026 (5) | 0.0001 (5) |
C3 | 0.0515 (7) | 0.0464 (7) | 0.0351 (6) | −0.0017 (6) | 0.0052 (5) | 0.0019 (5) |
C4 | 0.0501 (7) | 0.0464 (7) | 0.0352 (6) | −0.0017 (6) | 0.0037 (5) | −0.0016 (5) |
C5 | 0.0531 (8) | 0.0470 (7) | 0.0394 (7) | 0.0002 (6) | 0.0057 (6) | −0.0004 (6) |
C6 | 0.0493 (7) | 0.0497 (8) | 0.0409 (7) | 0.0008 (6) | 0.0023 (6) | −0.0061 (6) |
C7 | 0.0474 (7) | 0.0599 (8) | 0.0347 (6) | 0.0000 (6) | 0.0007 (5) | −0.0047 (6) |
C8 | 0.0535 (8) | 0.0553 (8) | 0.0353 (7) | −0.0045 (6) | 0.0008 (6) | 0.0007 (6) |
C9 | 0.0511 (7) | 0.0477 (7) | 0.0377 (6) | −0.0039 (6) | 0.0013 (5) | −0.0013 (5) |
C10 | 0.0822 (11) | 0.0573 (9) | 0.0412 (7) | −0.0124 (8) | −0.0046 (7) | 0.0039 (7) |
C11 | 0.0844 (12) | 0.0694 (10) | 0.0406 (8) | −0.0145 (9) | −0.0045 (7) | 0.0070 (7) |
C12 | 0.0607 (9) | 0.0752 (10) | 0.0355 (7) | −0.0022 (8) | −0.0010 (6) | 0.0026 (7) |
C13 | 0.0658 (11) | 0.130 (2) | 0.0797 (14) | 0.0087 (12) | 0.0131 (10) | 0.0199 (13) |
C14 | 0.0799 (11) | 0.0816 (12) | 0.0388 (8) | 0.0012 (9) | −0.0074 (7) | −0.0051 (8) |
C15 | 0.0586 (9) | 0.0533 (8) | 0.0470 (8) | −0.0032 (7) | −0.0004 (6) | −0.0094 (6) |
C16 | 0.0622 (9) | 0.0533 (8) | 0.0453 (7) | −0.0028 (7) | 0.0020 (6) | −0.0088 (6) |
C17 | 0.0734 (10) | 0.0547 (9) | 0.0539 (9) | 0.0028 (8) | −0.0071 (7) | −0.0124 (7) |
C18 | 0.0777 (13) | 0.0808 (13) | 0.0983 (15) | 0.0194 (10) | −0.0122 (11) | −0.0274 (12) |
C19 | 0.149 (2) | 0.0586 (12) | 0.1029 (18) | 0.0013 (13) | 0.0236 (16) | 0.0056 (11) |
C20 | 0.1201 (17) | 0.0736 (12) | 0.0521 (10) | 0.0323 (12) | −0.0078 (10) | −0.0004 (9) |
C21 | 0.0558 (8) | 0.0438 (7) | 0.0349 (6) | −0.0068 (6) | 0.0044 (6) | −0.0010 (5) |
C22 | 0.0640 (9) | 0.0497 (8) | 0.0386 (7) | 0.0052 (7) | 0.0069 (6) | −0.0022 (6) |
C23 | 0.0749 (10) | 0.0553 (9) | 0.0377 (7) | 0.0086 (7) | 0.0010 (7) | 0.0015 (6) |
C24 | 0.0738 (10) | 0.0481 (8) | 0.0341 (6) | −0.0044 (7) | 0.0047 (6) | −0.0028 (6) |
C25 | 0.0791 (10) | 0.0437 (7) | 0.0450 (8) | 0.0054 (7) | 0.0040 (7) | −0.0066 (6) |
C26 | 0.0716 (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—C9 | 1.3677 (17) | O1'—C9' | 1.3721 (16) |
O1—C1 | 1.3825 (16) | O1'—C1' | 1.3775 (16) |
O2—C1 | 1.2122 (18) | O2'—C1' | 1.2146 (18) |
O3—C3 | 1.3366 (16) | O3'—C3' | 1.3376 (16) |
O3—H3 | 0.86 (2) | O3'—H3' | 0.87 (2) |
O4—C5 | 1.3881 (17) | O4'—C5' | 1.3871 (16) |
O4—C20 | 1.447 (2) | O4'—C20' | 1.444 (2) |
O5—C7 | 1.3561 (16) | O5'—C7' | 1.3527 (15) |
O5—C12 | 1.4710 (19) | O5'—C12' | 1.4714 (18) |
O6—C24 | 1.3661 (17) | O6'—C24' | 1.3637 (17) |
O6—H6 | 0.87 (3) | O6'—H6' | 0.87 (3) |
C1—C2 | 1.4342 (19) | C1'—C2' | 1.4298 (19) |
C2—C3 | 1.3659 (19) | C2'—C3' | 1.3694 (19) |
C2—C21 | 1.4907 (18) | C2'—C21' | 1.4885 (17) |
C3—C4 | 1.4488 (18) | C3'—C4' | 1.4467 (17) |
C4—C9 | 1.3883 (19) | C4'—C9' | 1.3839 (18) |
C4—C5 | 1.4102 (19) | C4'—C5' | 1.4151 (18) |
C5—C6 | 1.3865 (19) | C5'—C6' | 1.3827 (18) |
C6—C7 | 1.403 (2) | C6'—C7' | 1.406 (2) |
C6—C15 | 1.512 (2) | C6'—C15' | 1.5090 (19) |
C7—C8 | 1.394 (2) | C7'—C8' | 1.391 (2) |
C8—C9 | 1.3950 (18) | C8'—C9' | 1.3907 (18) |
C8—C10 | 1.457 (2) | C8'—C10' | 1.455 (2) |
C10—C11 | 1.324 (2) | C10'—C11' | 1.321 (2) |
C10—H10 | 0.9300 | C10'—H10' | 0.9300 |
C11—C12 | 1.497 (2) | C11'—C12' | 1.493 (2) |
C11—H11 | 0.9300 | C11'—H11' | 0.9300 |
C12—C13 | 1.509 (3) | C12'—C14' | 1.517 (2) |
C12—C14 | 1.516 (2) | C12'—C13' | 1.518 (2) |
C13—H13A | 0.9600 | C13'—H13D | 0.9600 |
C13—H13B | 0.9600 | C13'—H13E | 0.9600 |
C13—H13C | 0.9600 | C13'—H13F | 0.9600 |
C14—H14A | 0.9600 | C14'—H14D | 0.9600 |
C14—H14B | 0.9600 | C14'—H14E | 0.9600 |
C14—H14C | 0.9600 | C14'—H14F | 0.9600 |
C15—C16 | 1.499 (2) | C15'—C16' | 1.503 (2) |
C15—H15A | 0.9700 | C15'—H15D | 0.9700 |
C15—H15B | 0.9700 | C15'—H15E | 0.9700 |
C16—C17 | 1.319 (2) | C16'—C17' | 1.315 (2) |
C16—H16 | 0.9300 | C16'—H16' | 0.9300 |
C17—C19 | 1.489 (3) | C17'—C19' | 1.489 (3) |
C17—C18 | 1.500 (3) | C17'—C18' | 1.503 (3) |
C18—H18A | 0.9600 | C18'—H18D | 0.9600 |
C18—H18B | 0.9600 | C18'—H18E | 0.9600 |
C18—H18C | 0.9600 | C18'—H18F | 0.9600 |
C19—H19A | 0.9600 | C19'—H19D | 0.9600 |
C19—H19B | 0.9600 | C19'—H19E | 0.9600 |
C19—H19C | 0.9600 | C19'—H19F | 0.9600 |
C20—H20A | 0.9600 | C20'—H20D | 0.9600 |
C20—H20B | 0.9600 | C20'—H20E | 0.9600 |
C20—H20C | 0.9600 | C20'—H20F | 0.9600 |
C21—C22 | 1.389 (2) | C21'—C22' | 1.382 (2) |
C21—C26 | 1.389 (2) | C21'—C26' | 1.390 (2) |
C22—C23 | 1.3786 (19) | C22'—C23' | 1.3824 (19) |
C22—H22 | 0.9300 | C22'—H22' | 0.9300 |
C23—C24 | 1.382 (2) | C23'—C24' | 1.376 (2) |
C23—H23 | 0.9300 | C23'—H23' | 0.9300 |
C24—C25 | 1.376 (2) | C24'—C25' | 1.379 (2) |
C25—C26 | 1.387 (2) | C25'—C26' | 1.3868 (19) |
C25—H25 | 0.9300 | C25'—H25' | 0.9300 |
C26—H26 | 0.9300 | C26'—H26' | 0.9300 |
| | | |
C9—O1—C1 | 122.25 (11) | C9'—O1'—C1' | 122.17 (11) |
C3—O3—H3 | 104.2 (15) | C3'—O3'—H3' | 103.9 (13) |
C5—O4—C20 | 113.51 (13) | C5'—O4'—C20' | 114.63 (13) |
C7—O5—C12 | 119.09 (12) | C7'—O5'—C12' | 120.92 (12) |
C24—O6—H6 | 108.0 (17) | C24'—O6'—H6' | 106.5 (16) |
O2—C1—O1 | 115.02 (12) | O2'—C1'—O1' | 115.02 (12) |
O2—C1—C2 | 126.15 (13) | O2'—C1'—C2' | 125.87 (13) |
O1—C1—C2 | 118.82 (12) | O1'—C1'—C2' | 119.10 (12) |
C3—C2—C1 | 118.83 (12) | C3'—C2'—C1' | 118.61 (12) |
C3—C2—C21 | 122.35 (12) | C3'—C2'—C21' | 122.58 (12) |
C1—C2—C21 | 118.82 (12) | C1'—C2'—C21' | 118.79 (12) |
O3—C3—C2 | 118.97 (12) | O3'—C3'—C2' | 118.80 (12) |
O3—C3—C4 | 119.40 (12) | O3'—C3'—C4' | 119.64 (12) |
C2—C3—C4 | 121.63 (12) | C2'—C3'—C4' | 121.56 (12) |
C9—C4—C5 | 117.44 (12) | C9'—C4'—C5' | 117.37 (11) |
C9—C4—C3 | 117.39 (12) | C9'—C4'—C3' | 117.58 (12) |
C5—C4—C3 | 125.14 (12) | C5'—C4'—C3' | 125.05 (12) |
C6—C5—O4 | 119.47 (12) | C6'—C5'—O4' | 120.03 (12) |
C6—C5—C4 | 122.43 (13) | C6'—C5'—C4' | 122.12 (12) |
O4—C5—C4 | 118.08 (12) | O4'—C5'—C4' | 117.81 (11) |
C5—C6—C7 | 117.09 (13) | C5'—C6'—C7' | 117.33 (12) |
C5—C6—C15 | 122.60 (13) | C5'—C6'—C15' | 122.81 (13) |
C7—C6—C15 | 120.30 (12) | C7'—C6'—C15' | 119.86 (12) |
O5—C7—C8 | 120.54 (13) | O5'—C7'—C8' | 121.38 (12) |
O5—C7—C6 | 116.20 (13) | O5'—C7'—C6' | 115.51 (12) |
C8—C7—C6 | 123.14 (12) | C8'—C7'—C6' | 123.00 (12) |
C7—C8—C9 | 116.97 (13) | C9'—C8'—C7' | 116.92 (12) |
C7—C8—C10 | 118.55 (13) | C9'—C8'—C10' | 124.32 (13) |
C9—C8—C10 | 124.38 (14) | C7'—C8'—C10' | 118.67 (12) |
O1—C9—C4 | 120.87 (12) | O1'—C9'—C4' | 120.68 (11) |
O1—C9—C8 | 116.23 (12) | O1'—C9'—C8' | 116.06 (12) |
C4—C9—C8 | 122.89 (13) | C4'—C9'—C8' | 123.25 (13) |
C11—C10—C8 | 119.46 (16) | C11'—C10'—C8' | 119.59 (15) |
C11—C10—H10 | 120.3 | C11'—C10'—H10' | 120.2 |
C8—C10—H10 | 120.3 | C8'—C10'—H10' | 120.2 |
C10—C11—C12 | 121.97 (15) | C10'—C11'—C12' | 123.27 (15) |
C10—C11—H11 | 119.0 | C10'—C11'—H11' | 118.4 |
C12—C11—H11 | 119.0 | C12'—C11'—H11' | 118.4 |
O5—C12—C11 | 110.45 (12) | O5'—C12'—C11' | 111.46 (11) |
O5—C12—C13 | 107.26 (14) | O5'—C12'—C14' | 104.41 (13) |
C11—C12—C13 | 110.21 (17) | C11'—C12'—C14' | 111.75 (14) |
O5—C12—C14 | 104.41 (13) | O5'—C12'—C13' | 106.91 (15) |
C11—C12—C14 | 112.33 (14) | C11'—C12'—C13' | 110.88 (17) |
C13—C12—C14 | 111.92 (15) | C14'—C12'—C13' | 111.16 (13) |
C12—C13—H13A | 109.5 | C12'—C13'—H13D | 109.5 |
C12—C13—H13B | 109.5 | C12'—C13'—H13E | 109.5 |
H13A—C13—H13B | 109.5 | H13D—C13'—H13E | 109.5 |
C12—C13—H13C | 109.5 | C12'—C13'—H13F | 109.5 |
H13A—C13—H13C | 109.5 | H13D—C13'—H13F | 109.5 |
H13B—C13—H13C | 109.5 | H13E—C13'—H13F | 109.5 |
C12—C14—H14A | 109.5 | C12'—C14'—H14D | 109.5 |
C12—C14—H14B | 109.5 | C12'—C14'—H14E | 109.5 |
H14A—C14—H14B | 109.5 | H14D—C14'—H14E | 109.5 |
C12—C14—H14C | 109.5 | C12'—C14'—H14F | 109.5 |
H14A—C14—H14C | 109.5 | H14D—C14'—H14F | 109.5 |
H14B—C14—H14C | 109.5 | H14E—C14'—H14F | 109.5 |
C16—C15—C6 | 112.25 (13) | C16'—C15'—C6' | 112.12 (12) |
C16—C15—H15A | 109.2 | C16'—C15'—H15D | 109.2 |
C6—C15—H15A | 109.2 | C6'—C15'—H15D | 109.2 |
C16—C15—H15B | 109.2 | C16'—C15'—H15E | 109.2 |
C6—C15—H15B | 109.2 | C6'—C15'—H15E | 109.2 |
H15A—C15—H15B | 107.9 | H15D—C15'—H15E | 107.9 |
C17—C16—C15 | 128.00 (16) | C17'—C16'—C15' | 127.30 (15) |
C17—C16—H16 | 116.0 | C17'—C16'—H16' | 116.4 |
C15—C16—H16 | 116.0 | C15'—C16'—H16' | 116.4 |
C16—C17—C19 | 124.15 (18) | C16'—C17'—C19' | 123.83 (17) |
C16—C17—C18 | 120.92 (18) | C16'—C17'—C18' | 120.91 (17) |
C19—C17—C18 | 114.91 (18) | C19'—C17'—C18' | 115.25 (17) |
C17—C18—H18A | 109.5 | C17'—C18'—H18D | 109.5 |
C17—C18—H18B | 109.5 | C17'—C18'—H18E | 109.5 |
H18A—C18—H18B | 109.5 | H18D—C18'—H18E | 109.5 |
C17—C18—H18C | 109.5 | C17'—C18'—H18F | 109.5 |
H18A—C18—H18C | 109.5 | H18D—C18'—H18F | 109.5 |
H18B—C18—H18C | 109.5 | H18E—C18'—H18F | 109.5 |
C17—C19—H19A | 109.5 | C17'—C19'—H19D | 109.5 |
C17—C19—H19B | 109.5 | C17'—C19'—H19E | 109.5 |
H19A—C19—H19B | 109.5 | H19D—C19'—H19E | 109.5 |
C17—C19—H19C | 109.5 | C17'—C19'—H19F | 109.5 |
H19A—C19—H19C | 109.5 | H19D—C19'—H19F | 109.5 |
H19B—C19—H19C | 109.5 | H19E—C19'—H19F | 109.5 |
O4—C20—H20A | 109.5 | O4'—C20'—H20D | 109.5 |
O4—C20—H20B | 109.5 | O4'—C20'—H20E | 109.5 |
H20A—C20—H20B | 109.5 | H20D—C20'—H20E | 109.5 |
O4—C20—H20C | 109.5 | O4'—C20'—H20F | 109.5 |
H20A—C20—H20C | 109.5 | H20D—C20'—H20F | 109.5 |
H20B—C20—H20C | 109.5 | H20E—C20'—H20F | 109.5 |
C22—C21—C26 | 117.31 (12) | C22'—C21'—C26' | 117.72 (12) |
C22—C21—C2 | 120.84 (12) | C22'—C21'—C2' | 119.46 (12) |
C26—C21—C2 | 121.85 (13) | C26'—C21'—C2' | 122.80 (13) |
C23—C22—C21 | 121.72 (14) | C21'—C22'—C23' | 121.70 (14) |
C23—C22—H22 | 119.1 | C21'—C22'—H22' | 119.1 |
C21—C22—H22 | 119.1 | C23'—C22'—H22' | 119.1 |
C22—C23—C24 | 120.05 (14) | C24'—C23'—C22' | 119.85 (14) |
C22—C23—H23 | 120.0 | C24'—C23'—H23' | 120.1 |
C24—C23—H23 | 120.0 | C22'—C23'—H23' | 120.1 |
O6—C24—C25 | 122.95 (14) | O6'—C24'—C23' | 117.37 (14) |
O6—C24—C23 | 117.62 (14) | O6'—C24'—C25' | 123.04 (14) |
C25—C24—C23 | 119.42 (13) | C23'—C24'—C25' | 119.59 (13) |
C24—C25—C26 | 120.15 (14) | C24'—C25'—C26' | 120.15 (14) |
C24—C25—H25 | 119.9 | C24'—C25'—H25' | 119.9 |
C26—C25—H25 | 119.9 | C26'—C25'—H25' | 119.9 |
C25—C26—C21 | 121.34 (14) | C25'—C26'—C21' | 120.91 (14) |
C25—C26—H26 | 119.3 | C25'—C26'—H26' | 119.5 |
C21—C26—H26 | 119.3 | C21'—C26'—H26' | 119.5 |
| | | |
C9—O1—C1—O2 | 177.79 (14) | C9'—O1'—C1'—O2' | 176.52 (14) |
C9—O1—C1—C2 | −3.5 (2) | C9'—O1'—C1'—C2' | −4.5 (2) |
O2—C1—C2—C3 | 179.51 (17) | O2'—C1'—C2'—C3' | 178.76 (17) |
O1—C1—C2—C3 | 1.0 (2) | O1'—C1'—C2'—C3' | −0.1 (2) |
O2—C1—C2—C21 | −0.3 (3) | O2'—C1'—C2'—C21' | −3.0 (3) |
O1—C1—C2—C21 | −178.78 (12) | O1'—C1'—C2'—C21' | 178.08 (13) |
C1—C2—C3—O3 | −175.61 (13) | C1'—C2'—C3'—O3' | −175.39 (13) |
C21—C2—C3—O3 | 4.2 (2) | C21'—C2'—C3'—O3' | 6.5 (2) |
C1—C2—C3—C4 | 3.2 (2) | C1'—C2'—C3'—C4' | 4.6 (2) |
C21—C2—C3—C4 | −177.02 (13) | C21'—C2'—C3'—C4' | −173.52 (13) |
O3—C3—C4—C9 | 173.87 (13) | O3'—C3'—C4'—C9' | 175.38 (13) |
C2—C3—C4—C9 | −4.9 (2) | C2'—C3'—C4'—C9' | −4.6 (2) |
O3—C3—C4—C5 | −4.5 (2) | O3'—C3'—C4'—C5' | −4.7 (2) |
C2—C3—C4—C5 | 176.64 (14) | C2'—C3'—C4'—C5' | 175.26 (14) |
C20—O4—C5—C6 | 85.63 (17) | C20'—O4'—C5'—C6' | 80.65 (17) |
C20—O4—C5—C4 | −96.00 (16) | C20'—O4'—C5'—C4' | −101.76 (15) |
C9—C4—C5—C6 | −2.2 (2) | C9'—C4'—C5'—C6' | −0.9 (2) |
C3—C4—C5—C6 | 176.26 (13) | C3'—C4'—C5'—C6' | 179.23 (13) |
C9—C4—C5—O4 | 179.54 (13) | C9'—C4'—C5'—O4' | −178.42 (12) |
C3—C4—C5—O4 | −2.1 (2) | C3'—C4'—C5'—O4' | 1.7 (2) |
O4—C5—C6—C7 | 179.71 (13) | O4'—C5'—C6'—C7' | 177.66 (12) |
C4—C5—C6—C7 | 1.4 (2) | C4'—C5'—C6'—C7' | 0.2 (2) |
O4—C5—C6—C15 | −1.2 (2) | O4'—C5'—C6'—C15' | −2.9 (2) |
C4—C5—C6—C15 | −179.52 (13) | C4'—C5'—C6'—C15' | 179.63 (13) |
C12—O5—C7—C8 | 25.4 (2) | C12'—O5'—C7'—C8' | 17.9 (2) |
C12—O5—C7—C6 | −158.46 (13) | C12'—O5'—C7'—C6' | −165.89 (13) |
C5—C6—C7—O5 | −176.64 (12) | C5'—C6'—C7'—O5' | −176.16 (12) |
C15—C6—C7—O5 | 4.3 (2) | C15'—C6'—C7'—O5' | 4.37 (19) |
C5—C6—C7—C8 | −0.6 (2) | C5'—C6'—C7'—C8' | 0.0 (2) |
C15—C6—C7—C8 | −179.68 (14) | C15'—C6'—C7'—C8' | −179.48 (13) |
O5—C7—C8—C9 | 176.41 (13) | O5'—C7'—C8'—C9' | 176.48 (13) |
C6—C7—C8—C9 | 0.5 (2) | C6'—C7'—C8'—C9' | 0.5 (2) |
O5—C7—C8—C10 | 0.0 (2) | O5'—C7'—C8'—C10' | −0.3 (2) |
C6—C7—C8—C10 | −175.89 (14) | C6'—C7'—C8'—C10' | −176.23 (14) |
C1—O1—C9—C4 | 1.7 (2) | C1'—O1'—C9'—C4' | 4.5 (2) |
C1—O1—C9—C8 | −179.32 (13) | C1'—O1'—C9'—C8' | −176.76 (13) |
C5—C4—C9—O1 | −179.03 (13) | C5'—C4'—C9'—O1' | −179.84 (12) |
C3—C4—C9—O1 | 2.4 (2) | C3'—C4'—C9'—O1' | 0.1 (2) |
C5—C4—C9—C8 | 2.1 (2) | C5'—C4'—C9'—C8' | 1.5 (2) |
C3—C4—C9—C8 | −176.44 (13) | C3'—C4'—C9'—C8' | −178.61 (13) |
C7—C8—C9—O1 | 179.76 (13) | C7'—C8'—C9'—O1' | 179.95 (12) |
C10—C8—C9—O1 | −4.1 (2) | C10'—C8'—C9'—O1' | −3.5 (2) |
C7—C8—C9—C4 | −1.3 (2) | C7'—C8'—C9'—C4' | −1.3 (2) |
C10—C8—C9—C4 | 174.87 (15) | C10'—C8'—C9'—C4' | 175.26 (14) |
C7—C8—C10—C11 | −11.0 (2) | C9'—C8'—C10'—C11' | 176.27 (16) |
C9—C8—C10—C11 | 172.87 (16) | C7'—C8'—C10'—C11' | −7.2 (2) |
C8—C10—C11—C12 | −3.7 (3) | C8'—C10'—C11'—C12' | −3.0 (3) |
C7—O5—C12—C11 | −36.88 (18) | C7'—O5'—C12'—C11' | −25.7 (2) |
C7—O5—C12—C13 | 83.24 (18) | C7'—O5'—C12'—C14' | −146.46 (14) |
C7—O5—C12—C14 | −157.85 (13) | C7'—O5'—C12'—C13' | 95.66 (17) |
C10—C11—C12—O5 | 26.2 (2) | C10'—C11'—C12'—O5' | 18.4 (2) |
C10—C11—C12—C13 | −92.1 (2) | C10'—C11'—C12'—C14' | 134.79 (18) |
C10—C11—C12—C14 | 142.34 (18) | C10'—C11'—C12'—C13' | −100.6 (2) |
C5—C6—C15—C16 | −95.25 (17) | C5'—C6'—C15'—C16' | −98.91 (16) |
C7—C6—C15—C16 | 83.78 (17) | C7'—C6'—C15'—C16' | 80.53 (16) |
C6—C15—C16—C17 | 133.04 (17) | C6'—C15'—C16'—C17' | 138.78 (16) |
C15—C16—C17—C19 | 1.8 (3) | C15'—C16'—C17'—C19' | 0.6 (3) |
C15—C16—C17—C18 | −176.50 (15) | C15'—C16'—C17'—C18' | −178.52 (16) |
C3—C2—C21—C22 | 45.3 (2) | C3'—C2'—C21'—C22' | 45.2 (2) |
C1—C2—C21—C22 | −134.94 (15) | C1'—C2'—C21'—C22' | −132.93 (15) |
C3—C2—C21—C26 | −134.26 (16) | C3'—C2'—C21'—C26' | −136.40 (15) |
C1—C2—C21—C26 | 45.5 (2) | C1'—C2'—C21'—C26' | 45.5 (2) |
C26—C21—C22—C23 | 0.0 (2) | C26'—C21'—C22'—C23' | −2.1 (2) |
C2—C21—C22—C23 | −179.53 (14) | C2'—C21'—C22'—C23' | 176.41 (14) |
C21—C22—C23—C24 | 0.1 (2) | C21'—C22'—C23'—C24' | 1.3 (2) |
C22—C23—C24—O6 | 179.88 (15) | C22'—C23'—C24'—O6' | −178.97 (15) |
C22—C23—C24—C25 | 0.3 (2) | C22'—C23'—C24'—C25' | 1.2 (2) |
O6—C24—C25—C26 | 179.61 (16) | O6'—C24'—C25'—C26' | 177.26 (15) |
C23—C24—C25—C26 | −0.8 (2) | C23'—C24'—C25'—C26' | −3.0 (2) |
C24—C25—C26—C21 | 1.0 (3) | C24'—C25'—C26'—C21' | 2.2 (2) |
C22—C21—C26—C25 | −0.6 (2) | C22'—C21'—C26'—C25' | 0.3 (2) |
C2—C21—C26—C25 | 178.98 (14) | C2'—C21'—C26'—C25' | −178.12 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4 | 0.86 (2) | 1.80 (2) | 2.605 (2) | 156 (2) |
O6—H6···O2i | 0.87 (3) | 1.85 (3) | 2.699 (2) | 164 (2) |
O3′—H3′···O4′ | 0.87 (2) | 1.79 (2) | 2.601 (1) | 154 (2) |
O6′—H6′···O2′ii | 0.87 (3) | 1.82 (3) | 2.649 (2) | 158 (2) |
C11′—H11′···O6′iii | 0.93 | 2.55 | 3.325 (2) | 141 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+1/2, z+1/2; (iii) x, y, z−1. |