The title compound [systematic name: 5-hydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-3,6,7-trimethoxy-4
H-chromen-4-one], C
20H
20O
9, was isolated from the seeds of
Cleom viscosa Linn. Two independent molecules (
A and
B) are present in the asymmetric unit with almost similar conformations. The dihedral angles between the fused chromene ring system and the benzene ring bonded to it in molecules
A and
B are 4.2 (1) and 12.7 (1)°, respectively. The hydroxy O atoms are involved in intramolecular hydrogen bonding. The molecules are linked by C-H
O and O-H
O interactions into chains of edge-fused
R33(22) rings. Aromatic
-
and weak C-H
(arene) interactions are also observed.
Supporting information
CCDC reference: 618628
The dried and ground seeds of Cleome viscosa Linn. (4 kg) were soaked in CHCl3:MeOH (1:1) (8 l) for two weeks. The crude extract was suspended in hexane–ethyl acetate (9:1) and then fractionated by silica-gel chromatography using increasing proportions of hexane:ethyl acetate as eluant, to obtain compound (I) (Mahender, 2006). Crystals were grown from an MeOH–water (1:1) solution by slow evaporation.
All H atoms were placed in geometrically idealized positions and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å and O—H = 0.82 Å, and with Uiso(H) = 1.5Ueq(C,O) for methyl or hydroxy H atoms or 1.2Ueq(C) for all others. [Please check added text]
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: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
5-hydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-3,6,7-trimethoxy-4
H-chromene-4-one
top
Crystal data top
C20H20O9 | Z = 4 |
Mr = 404.36 | F(000) = 848 |
Triclinic, P1 | Dx = 1.445 Mg m−3 |
a = 7.5629 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 15.2199 (9) Å | Cell parameters from 5057 reflections |
c = 17.6543 (11) Å | θ = 2.2–27.2° |
α = 69.621 (1)° | µ = 0.12 mm−1 |
β = 83.145 (1)° | T = 273 K |
γ = 77.760 (1)° | Prism, colourless |
V = 1859.3 (2) Å3 | 0.22 × 0.18 × 0.16 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 6127 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 28.0°, θmin = 2.2° |
ω scans | h = −9→9 |
16152 measured reflections | k = −20→19 |
8323 independent reflections | l = −22→22 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0608P)2 + 0.4046P] where P = (Fo2 + 2Fc2)/3 |
8323 reflections | (Δ/σ)max < 0.001 |
537 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Crystal data top
C20H20O9 | γ = 77.760 (1)° |
Mr = 404.36 | V = 1859.3 (2) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.5629 (5) Å | Mo Kα radiation |
b = 15.2199 (9) Å | µ = 0.12 mm−1 |
c = 17.6543 (11) Å | T = 273 K |
α = 69.621 (1)° | 0.22 × 0.18 × 0.16 mm |
β = 83.145 (1)° | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 6127 reflections with I > 2σ(I) |
16152 measured reflections | Rint = 0.019 |
8323 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.24 e Å−3 |
8323 reflections | Δρmin = −0.22 e Å−3 |
537 parameters | |
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. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1A | 0.3907 (2) | −0.01377 (12) | 0.37569 (10) | 0.0392 (4) | |
C2A | 0.4328 (2) | −0.10321 (11) | 0.43907 (10) | 0.0370 (4) | |
C3A | 0.5430 (2) | −0.18467 (12) | 0.42496 (11) | 0.0412 (4) | |
C4A | 0.5896 (2) | −0.26713 (12) | 0.48888 (11) | 0.0420 (4) | |
C5A | 0.5293 (2) | −0.27050 (12) | 0.56833 (11) | 0.0420 (4) | |
C6A | 0.4179 (2) | −0.19286 (12) | 0.58362 (11) | 0.0414 (4) | |
H6A | 0.3760 | −0.1955 | 0.6359 | 0.050* | |
C7A | 0.3715 (2) | −0.11139 (11) | 0.51821 (10) | 0.0357 (4) | |
C8A | 0.2118 (2) | 0.04939 (11) | 0.47697 (10) | 0.0342 (3) | |
C9A | 0.2712 (2) | 0.06171 (11) | 0.39850 (10) | 0.0373 (4) | |
C10A | 0.6183 (3) | −0.42100 (14) | 0.48411 (14) | 0.0634 (6) | |
H10A | 0.5143 | −0.3988 | 0.4516 | 0.095* | |
H10B | 0.5808 | −0.4483 | 0.5399 | 0.095* | |
H10C | 0.7016 | −0.4684 | 0.4670 | 0.095* | |
C11A | 0.5470 (4) | −0.36044 (15) | 0.70907 (13) | 0.0675 (6) | |
H11A | 0.4183 | −0.3552 | 0.7195 | 0.101* | |
H11B | 0.5862 | −0.3100 | 0.7196 | 0.101* | |
H11C | 0.6068 | −0.4209 | 0.7437 | 0.101* | |
C12A | 0.1033 (3) | 0.15391 (16) | 0.28324 (13) | 0.0649 (6) | |
H12A | −0.0139 | 0.1508 | 0.3107 | 0.097* | |
H12B | 0.1396 | 0.1016 | 0.2629 | 0.097* | |
H12C | 0.0979 | 0.2129 | 0.2390 | 0.097* | |
C13A | 0.0961 (2) | 0.11803 (11) | 0.51211 (10) | 0.0359 (4) | |
C14A | 0.0352 (2) | 0.21234 (12) | 0.46458 (10) | 0.0405 (4) | |
H14A | 0.0632 | 0.2322 | 0.4092 | 0.049* | |
C15A | −0.0671 (2) | 0.27660 (12) | 0.49982 (11) | 0.0420 (4) | |
C16A | −0.1089 (2) | 0.24704 (12) | 0.58228 (11) | 0.0422 (4) | |
C17A | −0.0539 (2) | 0.15281 (13) | 0.62867 (11) | 0.0453 (4) | |
C18A | 0.0496 (2) | 0.08846 (12) | 0.59467 (11) | 0.0418 (4) | |
H18A | 0.0882 | 0.0256 | 0.6268 | 0.050* | |
C19A | −0.0781 (4) | 0.40433 (15) | 0.37563 (13) | 0.0735 (7) | |
H19A | −0.1246 | 0.3716 | 0.3469 | 0.110* | |
H19B | 0.0518 | 0.3937 | 0.3693 | 0.110* | |
H19C | −0.1253 | 0.4714 | 0.3543 | 0.110* | |
C20A | −0.1020 (3) | 0.37206 (16) | 0.63045 (14) | 0.0653 (6) | |
H20A | −0.0674 | 0.4130 | 0.5781 | 0.098* | |
H20B | 0.0047 | 0.3360 | 0.6589 | 0.098* | |
H20C | −0.1737 | 0.4100 | 0.6605 | 0.098* | |
O1A | 0.26342 (15) | −0.03581 (7) | 0.53572 (7) | 0.0388 (3) | |
O2A | 0.45445 (19) | −0.00009 (9) | 0.30425 (8) | 0.0524 (3) | |
O3A | 0.6038 (2) | −0.18191 (9) | 0.34934 (8) | 0.0575 (4) | |
H3A | 0.5772 | −0.1274 | 0.3180 | 0.086* | |
O4A | 0.70446 (17) | −0.34325 (9) | 0.47488 (9) | 0.0550 (3) | |
O5A | 0.59107 (19) | −0.35347 (9) | 0.62640 (8) | 0.0555 (3) | |
O6A | 0.23295 (17) | 0.14845 (8) | 0.33891 (7) | 0.0448 (3) | |
O7A | −0.13092 (19) | 0.36948 (9) | 0.45837 (8) | 0.0583 (4) | |
O8A | −0.20616 (17) | 0.30792 (10) | 0.62120 (8) | 0.0552 (3) | |
O9A | −0.1010 (2) | 0.12297 (11) | 0.70954 (8) | 0.0723 (5) | |
H9A | −0.1795 | 0.1640 | 0.7200 | 0.108* | |
C1B | 1.2373 (2) | −0.17055 (14) | 0.08625 (11) | 0.0479 (4) | |
C2B | 1.1070 (2) | −0.23139 (13) | 0.12285 (11) | 0.0439 (4) | |
C3B | 1.1454 (3) | −0.33054 (14) | 0.13385 (12) | 0.0494 (5) | |
C4B | 1.0189 (3) | −0.38680 (13) | 0.17088 (12) | 0.0501 (5) | |
C5B | 0.8476 (3) | −0.34519 (13) | 0.19619 (11) | 0.0469 (4) | |
C6B | 0.8065 (2) | −0.24875 (12) | 0.18592 (11) | 0.0446 (4) | |
H6B | 0.6937 | −0.2216 | 0.2030 | 0.053* | |
C7B | 0.9368 (2) | −0.19385 (12) | 0.14982 (10) | 0.0406 (4) | |
C8B | 1.0128 (2) | −0.03991 (12) | 0.11122 (10) | 0.0385 (4) | |
C9B | 1.1810 (2) | −0.07229 (13) | 0.08330 (10) | 0.0433 (4) | |
C10B | 1.0251 (5) | −0.51783 (19) | 0.12832 (19) | 0.1049 (11) | |
H10D | 0.8970 | −0.5032 | 0.1213 | 0.157* | |
H10E | 1.0657 | −0.5856 | 0.1446 | 0.157* | |
H10F | 1.0872 | −0.4879 | 0.0782 | 0.157* | |
C11B | 0.5600 (3) | −0.36933 (17) | 0.26295 (16) | 0.0727 (6) | |
H11D | 0.5788 | −0.3390 | 0.3000 | 0.109* | |
H11E | 0.4962 | −0.4207 | 0.2908 | 0.109* | |
H11F | 0.4901 | −0.3237 | 0.2194 | 0.109* | |
C12B | 1.4323 (3) | −0.01767 (19) | 0.10558 (15) | 0.0740 (7) | |
H12D | 1.3704 | −0.0091 | 0.1539 | 0.111* | |
H12E | 1.5029 | 0.0314 | 0.0806 | 0.111* | |
H12F | 1.5107 | −0.0789 | 0.1190 | 0.111* | |
C13B | 0.9394 (2) | 0.05572 (12) | 0.11613 (10) | 0.0385 (4) | |
C14B | 1.0266 (2) | 0.13294 (12) | 0.07688 (10) | 0.0425 (4) | |
H14B | 1.1311 | 0.1254 | 0.0444 | 0.051* | |
C15B | 0.9582 (2) | 0.22054 (12) | 0.08606 (10) | 0.0430 (4) | |
C16B | 0.7992 (3) | 0.23370 (12) | 0.13260 (11) | 0.0443 (4) | |
C17B | 0.7108 (2) | 0.15706 (13) | 0.17119 (11) | 0.0447 (4) | |
C18B | 0.7814 (2) | 0.06876 (12) | 0.16352 (11) | 0.0423 (4) | |
H18B | 0.7228 | 0.0176 | 0.1902 | 0.051* | |
C19B | 1.2221 (3) | 0.28292 (16) | 0.02194 (14) | 0.0640 (6) | |
H19D | 1.2950 | 0.2358 | 0.0636 | 0.096* | |
H19E | 1.2675 | 0.3415 | 0.0047 | 0.096* | |
H19F | 1.2268 | 0.2610 | −0.0232 | 0.096* | |
C20B | 0.6144 (4) | 0.38522 (17) | 0.09036 (17) | 0.0889 (8) | |
H20D | 0.6683 | 0.3976 | 0.0365 | 0.133* | |
H20E | 0.5832 | 0.4436 | 0.1025 | 0.133* | |
H20F | 0.5070 | 0.3594 | 0.0942 | 0.133* | |
O1B | 0.89050 (15) | −0.09924 (8) | 0.14122 (7) | 0.0429 (3) | |
O2B | 1.39150 (19) | −0.20068 (11) | 0.06065 (10) | 0.0674 (4) | |
O3B | 1.3092 (2) | −0.36996 (11) | 0.10888 (11) | 0.0681 (4) | |
H3B | 1.3709 | −0.3286 | 0.0880 | 0.102* | |
O4B | 1.0624 (2) | −0.48396 (9) | 0.18801 (9) | 0.0685 (4) | |
O5B | 0.7314 (2) | −0.40605 (9) | 0.23112 (9) | 0.0605 (4) | |
O6B | 1.30210 (17) | −0.01232 (9) | 0.05055 (8) | 0.0523 (3) | |
O7B | 1.03974 (19) | 0.29848 (9) | 0.05259 (9) | 0.0595 (4) | |
O8B | 0.73797 (19) | 0.31948 (9) | 0.14574 (8) | 0.0558 (3) | |
O9B | 0.5573 (2) | 0.17353 (9) | 0.21665 (10) | 0.0639 (4) | |
H9B | 0.5228 | 0.1231 | 0.2412 | 0.096* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0410 (9) | 0.0395 (9) | 0.0429 (9) | −0.0121 (7) | 0.0007 (7) | −0.0188 (7) |
C2A | 0.0349 (8) | 0.0355 (8) | 0.0451 (9) | −0.0082 (7) | −0.0001 (7) | −0.0187 (7) |
C3A | 0.0383 (9) | 0.0422 (9) | 0.0496 (10) | −0.0099 (7) | 0.0053 (8) | −0.0244 (8) |
C4A | 0.0338 (9) | 0.0367 (9) | 0.0594 (11) | −0.0034 (7) | 0.0023 (8) | −0.0242 (8) |
C5A | 0.0389 (9) | 0.0352 (9) | 0.0522 (10) | −0.0028 (7) | −0.0040 (8) | −0.0167 (8) |
C6A | 0.0412 (9) | 0.0389 (9) | 0.0445 (10) | −0.0042 (7) | 0.0001 (7) | −0.0168 (8) |
C7A | 0.0326 (8) | 0.0324 (8) | 0.0467 (9) | −0.0052 (6) | −0.0018 (7) | −0.0196 (7) |
C8A | 0.0332 (8) | 0.0298 (8) | 0.0412 (9) | −0.0063 (6) | −0.0037 (7) | −0.0129 (7) |
C9A | 0.0393 (9) | 0.0332 (8) | 0.0419 (9) | −0.0091 (7) | −0.0037 (7) | −0.0136 (7) |
C10A | 0.0753 (14) | 0.0407 (11) | 0.0781 (15) | −0.0007 (10) | −0.0066 (12) | −0.0295 (10) |
C11A | 0.0898 (17) | 0.0480 (12) | 0.0523 (12) | 0.0098 (11) | −0.0113 (11) | −0.0119 (10) |
C12A | 0.0757 (15) | 0.0619 (13) | 0.0525 (12) | −0.0036 (11) | −0.0205 (11) | −0.0130 (10) |
C13A | 0.0325 (8) | 0.0344 (8) | 0.0442 (9) | −0.0065 (6) | −0.0035 (7) | −0.0167 (7) |
C14A | 0.0429 (9) | 0.0373 (9) | 0.0394 (9) | −0.0014 (7) | −0.0019 (7) | −0.0141 (7) |
C15A | 0.0372 (9) | 0.0346 (9) | 0.0512 (10) | 0.0012 (7) | −0.0053 (8) | −0.0142 (8) |
C16A | 0.0347 (9) | 0.0446 (10) | 0.0489 (10) | 0.0004 (7) | −0.0010 (7) | −0.0222 (8) |
C17A | 0.0452 (10) | 0.0486 (10) | 0.0400 (9) | −0.0040 (8) | 0.0003 (8) | −0.0156 (8) |
C18A | 0.0423 (9) | 0.0362 (9) | 0.0441 (10) | −0.0028 (7) | −0.0031 (7) | −0.0121 (7) |
C19A | 0.0945 (18) | 0.0463 (12) | 0.0569 (13) | 0.0149 (11) | −0.0022 (12) | −0.0055 (10) |
C20A | 0.0657 (13) | 0.0707 (14) | 0.0724 (14) | −0.0006 (11) | −0.0070 (11) | −0.0455 (12) |
O1A | 0.0436 (6) | 0.0313 (6) | 0.0401 (6) | −0.0007 (5) | −0.0004 (5) | −0.0143 (5) |
O2A | 0.0677 (9) | 0.0452 (7) | 0.0433 (7) | −0.0097 (6) | 0.0106 (6) | −0.0181 (6) |
O3A | 0.0725 (9) | 0.0485 (8) | 0.0528 (8) | −0.0072 (7) | 0.0146 (7) | −0.0265 (6) |
O4A | 0.0473 (7) | 0.0415 (7) | 0.0790 (10) | −0.0012 (6) | 0.0079 (7) | −0.0311 (7) |
O5A | 0.0640 (8) | 0.0402 (7) | 0.0552 (8) | 0.0092 (6) | −0.0062 (7) | −0.0172 (6) |
O6A | 0.0549 (7) | 0.0366 (6) | 0.0403 (7) | −0.0071 (5) | −0.0025 (6) | −0.0103 (5) |
O7A | 0.0684 (9) | 0.0394 (7) | 0.0520 (8) | 0.0129 (6) | 0.0010 (7) | −0.0111 (6) |
O8A | 0.0495 (8) | 0.0567 (8) | 0.0619 (8) | 0.0027 (6) | 0.0050 (6) | −0.0328 (7) |
O9A | 0.0931 (12) | 0.0646 (10) | 0.0421 (8) | 0.0085 (8) | 0.0109 (7) | −0.0144 (7) |
C1B | 0.0440 (10) | 0.0542 (11) | 0.0460 (10) | 0.0036 (8) | −0.0019 (8) | −0.0249 (9) |
C2B | 0.0462 (10) | 0.0439 (10) | 0.0424 (9) | 0.0012 (8) | −0.0043 (8) | −0.0202 (8) |
C3B | 0.0518 (11) | 0.0491 (11) | 0.0487 (11) | 0.0082 (9) | −0.0085 (9) | −0.0264 (9) |
C4B | 0.0628 (12) | 0.0373 (9) | 0.0493 (11) | 0.0040 (9) | −0.0119 (9) | −0.0180 (8) |
C5B | 0.0572 (11) | 0.0393 (10) | 0.0430 (10) | −0.0039 (8) | −0.0095 (8) | −0.0130 (8) |
C6B | 0.0457 (10) | 0.0397 (9) | 0.0475 (10) | −0.0007 (8) | −0.0037 (8) | −0.0174 (8) |
C7B | 0.0447 (10) | 0.0382 (9) | 0.0396 (9) | 0.0003 (7) | −0.0076 (7) | −0.0166 (7) |
C8B | 0.0403 (9) | 0.0411 (9) | 0.0349 (8) | −0.0054 (7) | −0.0037 (7) | −0.0140 (7) |
C9B | 0.0429 (10) | 0.0491 (10) | 0.0381 (9) | −0.0058 (8) | −0.0002 (7) | −0.0169 (8) |
C10B | 0.156 (3) | 0.0605 (16) | 0.118 (2) | −0.0132 (17) | −0.025 (2) | −0.0515 (17) |
C11B | 0.0671 (14) | 0.0593 (13) | 0.0865 (17) | −0.0164 (11) | 0.0094 (13) | −0.0192 (12) |
C12B | 0.0529 (13) | 0.0959 (18) | 0.0783 (16) | −0.0225 (12) | −0.0087 (11) | −0.0284 (14) |
C13B | 0.0401 (9) | 0.0400 (9) | 0.0362 (9) | −0.0043 (7) | −0.0050 (7) | −0.0146 (7) |
C14B | 0.0422 (9) | 0.0450 (10) | 0.0401 (9) | −0.0082 (8) | 0.0019 (7) | −0.0149 (8) |
C15B | 0.0486 (10) | 0.0428 (10) | 0.0400 (9) | −0.0146 (8) | −0.0016 (8) | −0.0131 (8) |
C16B | 0.0544 (11) | 0.0384 (9) | 0.0435 (10) | −0.0090 (8) | −0.0009 (8) | −0.0183 (8) |
C17B | 0.0467 (10) | 0.0441 (10) | 0.0454 (10) | −0.0096 (8) | 0.0050 (8) | −0.0191 (8) |
C18B | 0.0452 (10) | 0.0369 (9) | 0.0465 (10) | −0.0106 (7) | 0.0023 (8) | −0.0157 (8) |
C19B | 0.0570 (13) | 0.0665 (14) | 0.0689 (14) | −0.0267 (11) | 0.0078 (11) | −0.0174 (11) |
C20B | 0.110 (2) | 0.0575 (15) | 0.093 (2) | 0.0150 (14) | −0.0179 (17) | −0.0302 (14) |
O1B | 0.0398 (6) | 0.0352 (6) | 0.0550 (7) | −0.0026 (5) | −0.0004 (5) | −0.0195 (5) |
O2B | 0.0511 (8) | 0.0674 (9) | 0.0849 (11) | −0.0007 (7) | 0.0151 (8) | −0.0386 (8) |
O3B | 0.0590 (9) | 0.0609 (9) | 0.0884 (12) | 0.0080 (7) | 0.0042 (8) | −0.0433 (9) |
O4B | 0.0890 (11) | 0.0370 (7) | 0.0753 (10) | 0.0071 (7) | −0.0116 (8) | −0.0220 (7) |
O5B | 0.0690 (9) | 0.0391 (7) | 0.0685 (9) | −0.0093 (7) | 0.0008 (7) | −0.0134 (7) |
O6B | 0.0442 (7) | 0.0590 (8) | 0.0539 (8) | −0.0104 (6) | 0.0052 (6) | −0.0209 (6) |
O7B | 0.0616 (9) | 0.0469 (8) | 0.0714 (9) | −0.0218 (7) | 0.0139 (7) | −0.0199 (7) |
O8B | 0.0689 (9) | 0.0417 (7) | 0.0624 (9) | −0.0125 (6) | 0.0067 (7) | −0.0260 (6) |
O9B | 0.0668 (9) | 0.0449 (8) | 0.0794 (10) | −0.0148 (7) | 0.0323 (8) | −0.0289 (7) |
Geometric parameters (Å, º) top
C1A—O2A | 1.257 (2) | C1B—O2B | 1.252 (2) |
C1A—C2A | 1.431 (2) | C1B—C2B | 1.436 (3) |
C1A—C9A | 1.447 (2) | C1B—C9B | 1.450 (3) |
C2A—C7A | 1.390 (2) | C2B—C7B | 1.393 (2) |
C2A—C3A | 1.422 (2) | C2B—C3B | 1.422 (3) |
C3A—O3A | 1.348 (2) | C3B—O3B | 1.352 (2) |
C3A—C4A | 1.376 (2) | C3B—C4B | 1.373 (3) |
C4A—O4A | 1.371 (2) | C4B—O4B | 1.376 (2) |
C4A—C5A | 1.409 (3) | C4B—C5B | 1.410 (3) |
C5A—O5A | 1.351 (2) | C5B—O5B | 1.352 (2) |
C5A—C6A | 1.388 (2) | C5B—C6B | 1.385 (2) |
C6A—C7A | 1.382 (2) | C6B—C7B | 1.380 (3) |
C6A—H6A | 0.9300 | C6B—H6B | 0.9300 |
C7A—O1A | 1.370 (2) | C7B—O1B | 1.366 (2) |
C8A—O1A | 1.362 (2) | C8B—O1B | 1.362 (2) |
C8A—C9A | 1.365 (2) | C8B—C9B | 1.363 (2) |
C8A—C13A | 1.475 (2) | C8B—C13B | 1.472 (2) |
C9A—O6A | 1.370 (2) | C9B—O6B | 1.366 (2) |
C10A—O4A | 1.421 (2) | C10B—O4B | 1.402 (3) |
C10A—H10A | 0.9600 | C10B—H10D | 0.9600 |
C10A—H10B | 0.9600 | C10B—H10E | 0.9600 |
C10A—H10C | 0.9600 | C10B—H10F | 0.9600 |
C11A—O5A | 1.429 (2) | C11B—O5B | 1.430 (3) |
C11A—H11A | 0.9600 | C11B—H11D | 0.9600 |
C11A—H11B | 0.9600 | C11B—H11E | 0.9600 |
C11A—H11C | 0.9600 | C11B—H11F | 0.9600 |
C12A—O6A | 1.440 (2) | C12B—O6B | 1.435 (3) |
C12A—H12A | 0.9600 | C12B—H12D | 0.9600 |
C12A—H12B | 0.9600 | C12B—H12E | 0.9600 |
C12A—H12C | 0.9600 | C12B—H12F | 0.9600 |
C13A—C18A | 1.392 (2) | C13B—C18B | 1.394 (2) |
C13A—C14A | 1.396 (2) | C13B—C14B | 1.396 (2) |
C14A—C15A | 1.389 (2) | C14B—C15B | 1.382 (2) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—O7A | 1.357 (2) | C15B—O7B | 1.368 (2) |
C15A—C16A | 1.384 (3) | C15B—C16B | 1.392 (3) |
C16A—O8A | 1.380 (2) | C16B—O8B | 1.379 (2) |
C16A—C17A | 1.382 (2) | C16B—C17B | 1.393 (2) |
C17A—O9A | 1.366 (2) | C17B—O9B | 1.360 (2) |
C17A—C18A | 1.380 (2) | C17B—C18B | 1.384 (2) |
C18A—H18A | 0.9300 | C18B—H18B | 0.9300 |
C19A—O7A | 1.409 (2) | C19B—O7B | 1.423 (2) |
C19A—H19A | 0.9600 | C19B—H19D | 0.9600 |
C19A—H19B | 0.9600 | C19B—H19E | 0.9600 |
C19A—H19C | 0.9600 | C19B—H19F | 0.9600 |
C20A—O8A | 1.438 (2) | C20B—O8B | 1.404 (3) |
C20A—H20A | 0.9600 | C20B—H20D | 0.9600 |
C20A—H20B | 0.9600 | C20B—H20E | 0.9600 |
C20A—H20C | 0.9600 | C20B—H20F | 0.9600 |
O3A—H3A | 0.8200 | O3B—H3B | 0.8200 |
O9A—H9A | 0.8200 | O9B—H9B | 0.8200 |
| | | |
O2A—C1A—C2A | 122.64 (15) | O2B—C1B—C2B | 122.42 (17) |
O2A—C1A—C9A | 121.22 (15) | O2B—C1B—C9B | 121.91 (18) |
C2A—C1A—C9A | 116.13 (15) | C2B—C1B—C9B | 115.64 (15) |
C7A—C2A—C3A | 117.75 (15) | C7B—C2B—C3B | 117.70 (17) |
C7A—C2A—C1A | 119.89 (14) | C7B—C2B—C1B | 119.98 (16) |
C3A—C2A—C1A | 122.31 (15) | C3B—C2B—C1B | 122.32 (16) |
O3A—C3A—C4A | 119.39 (15) | O3B—C3B—C4B | 119.76 (17) |
O3A—C3A—C2A | 120.63 (16) | O3B—C3B—C2B | 119.64 (19) |
C4A—C3A—C2A | 119.98 (16) | C4B—C3B—C2B | 120.60 (17) |
O4A—C4A—C3A | 119.28 (16) | C3B—C4B—O4B | 120.32 (18) |
O4A—C4A—C5A | 120.60 (16) | C3B—C4B—C5B | 119.54 (16) |
C3A—C4A—C5A | 119.97 (15) | O4B—C4B—C5B | 120.00 (19) |
O5A—C5A—C6A | 124.10 (16) | O5B—C5B—C6B | 123.76 (17) |
O5A—C5A—C4A | 114.66 (14) | O5B—C5B—C4B | 115.23 (16) |
C6A—C5A—C4A | 121.23 (16) | C6B—C5B—C4B | 121.00 (18) |
C7A—C6A—C5A | 117.53 (16) | C7B—C6B—C5B | 118.47 (17) |
C7A—C6A—H6A | 121.2 | C7B—C6B—H6B | 120.8 |
C5A—C6A—H6A | 121.2 | C5B—C6B—H6B | 120.8 |
O1A—C7A—C6A | 115.89 (14) | O1B—C7B—C6B | 116.42 (15) |
O1A—C7A—C2A | 120.61 (14) | O1B—C7B—C2B | 120.92 (16) |
C6A—C7A—C2A | 123.47 (15) | C6B—C7B—C2B | 122.67 (16) |
O1A—C8A—C9A | 119.96 (14) | O1B—C8B—C9B | 120.43 (15) |
O1A—C8A—C13A | 110.64 (13) | O1B—C8B—C13B | 111.59 (14) |
C9A—C8A—C13A | 129.39 (15) | C9B—C8B—C13B | 127.96 (16) |
C8A—C9A—O6A | 121.44 (14) | C8B—C9B—O6B | 120.73 (16) |
C8A—C9A—C1A | 121.50 (15) | C8B—C9B—C1B | 121.62 (17) |
O6A—C9A—C1A | 116.84 (15) | O6B—C9B—C1B | 117.65 (16) |
O4A—C10A—H10A | 109.5 | O4B—C10B—H10D | 109.5 |
O4A—C10A—H10B | 109.5 | O4B—C10B—H10E | 109.5 |
H10A—C10A—H10B | 109.5 | H10D—C10B—H10E | 109.5 |
O4A—C10A—H10C | 109.5 | O4B—C10B—H10F | 109.5 |
H10A—C10A—H10C | 109.5 | H10D—C10B—H10F | 109.5 |
H10B—C10A—H10C | 109.5 | H10E—C10B—H10F | 109.5 |
O5A—C11A—H11A | 109.5 | O5B—C11B—H11D | 109.5 |
O5A—C11A—H11B | 109.5 | O5B—C11B—H11E | 109.5 |
H11A—C11A—H11B | 109.5 | H11D—C11B—H11E | 109.5 |
O5A—C11A—H11C | 109.5 | O5B—C11B—H11F | 109.5 |
H11A—C11A—H11C | 109.5 | H11D—C11B—H11F | 109.5 |
H11B—C11A—H11C | 109.5 | H11E—C11B—H11F | 109.5 |
O6A—C12A—H12A | 109.5 | O6B—C12B—H12D | 109.5 |
O6A—C12A—H12B | 109.5 | O6B—C12B—H12E | 109.5 |
H12A—C12A—H12B | 109.5 | H12D—C12B—H12E | 109.5 |
O6A—C12A—H12C | 109.5 | O6B—C12B—H12F | 109.5 |
H12A—C12A—H12C | 109.5 | H12D—C12B—H12F | 109.5 |
H12B—C12A—H12C | 109.5 | H12E—C12B—H12F | 109.5 |
C18A—C13A—C14A | 119.43 (15) | C18B—C13B—C14B | 119.05 (15) |
C18A—C13A—C8A | 119.20 (15) | C18B—C13B—C8B | 118.99 (15) |
C14A—C13A—C8A | 121.36 (15) | C14B—C13B—C8B | 121.93 (15) |
C15A—C14A—C13A | 120.20 (16) | C15B—C14B—C13B | 120.23 (16) |
C15A—C14A—H14A | 119.9 | C15B—C14B—H14B | 119.9 |
C13A—C14A—H14A | 119.9 | C13B—C14B—H14B | 119.9 |
O7A—C15A—C16A | 115.95 (15) | O7B—C15B—C14B | 123.80 (16) |
O7A—C15A—C14A | 124.13 (16) | O7B—C15B—C16B | 115.59 (15) |
C16A—C15A—C14A | 119.92 (15) | C14B—C15B—C16B | 120.60 (16) |
O8A—C16A—C17A | 117.58 (16) | O8B—C16B—C15B | 120.26 (16) |
O8A—C16A—C15A | 122.71 (16) | O8B—C16B—C17B | 120.22 (16) |
C17A—C16A—C15A | 119.71 (15) | C15B—C16B—C17B | 119.31 (16) |
O9A—C17A—C18A | 119.39 (16) | O9B—C17B—C18B | 122.96 (16) |
O9A—C17A—C16A | 119.64 (16) | O9B—C17B—C16B | 116.90 (15) |
C18A—C17A—C16A | 120.96 (17) | C18B—C17B—C16B | 120.14 (16) |
C17A—C18A—C13A | 119.72 (16) | C17B—C18B—C13B | 120.63 (16) |
C17A—C18A—H18A | 120.1 | C17B—C18B—H18B | 119.7 |
C13A—C18A—H18A | 120.1 | C13B—C18B—H18B | 119.7 |
O7A—C19A—H19A | 109.5 | O7B—C19B—H19D | 109.5 |
O7A—C19A—H19B | 109.5 | O7B—C19B—H19E | 109.5 |
H19A—C19A—H19B | 109.5 | H19D—C19B—H19E | 109.5 |
O7A—C19A—H19C | 109.5 | O7B—C19B—H19F | 109.5 |
H19A—C19A—H19C | 109.5 | H19D—C19B—H19F | 109.5 |
H19B—C19A—H19C | 109.5 | H19E—C19B—H19F | 109.5 |
O8A—C20A—H20A | 109.5 | O8B—C20B—H20D | 109.5 |
O8A—C20A—H20B | 109.5 | O8B—C20B—H20E | 109.5 |
H20A—C20A—H20B | 109.5 | H20D—C20B—H20E | 109.5 |
O8A—C20A—H20C | 109.5 | O8B—C20B—H20F | 109.5 |
H20A—C20A—H20C | 109.5 | H20D—C20B—H20F | 109.5 |
H20B—C20A—H20C | 109.5 | H20E—C20B—H20F | 109.5 |
C8A—O1A—C7A | 121.74 (13) | C8B—O1B—C7B | 121.21 (13) |
C3A—O3A—H3A | 109.5 | C3B—O3B—H3B | 109.5 |
C4A—O4A—C10A | 113.57 (14) | C4B—O4B—C10B | 115.82 (18) |
C5A—O5A—C11A | 118.25 (14) | C5B—O5B—C11B | 117.83 (15) |
C9A—O6A—C12A | 114.65 (14) | C9B—O6B—C12B | 114.20 (16) |
C15A—O7A—C19A | 117.61 (15) | C15B—O7B—C19B | 117.34 (15) |
C16A—O8A—C20A | 113.04 (14) | C16B—O8B—C20B | 115.04 (16) |
C17A—O9A—H9A | 109.5 | C17B—O9B—H9B | 109.5 |
| | | |
O2A—C1A—C2A—C7A | 174.12 (15) | O2B—C1B—C2B—C7B | −179.59 (17) |
C9A—C1A—C2A—C7A | −5.0 (2) | C9B—C1B—C2B—C7B | 2.5 (3) |
O2A—C1A—C2A—C3A | −3.2 (3) | O2B—C1B—C2B—C3B | 1.1 (3) |
C9A—C1A—C2A—C3A | 177.65 (15) | C9B—C1B—C2B—C3B | −176.82 (16) |
C7A—C2A—C3A—O3A | 178.67 (15) | C7B—C2B—C3B—O3B | −179.71 (17) |
C1A—C2A—C3A—O3A | −3.9 (3) | C1B—C2B—C3B—O3B | −0.4 (3) |
C7A—C2A—C3A—C4A | −1.8 (2) | C7B—C2B—C3B—C4B | −0.9 (3) |
C1A—C2A—C3A—C4A | 175.60 (16) | C1B—C2B—C3B—C4B | 178.41 (17) |
O3A—C3A—C4A—O4A | 3.3 (2) | O3B—C3B—C4B—O4B | 4.8 (3) |
C2A—C3A—C4A—O4A | −176.21 (15) | C2B—C3B—C4B—O4B | −174.04 (16) |
O3A—C3A—C4A—C5A | 179.00 (16) | O3B—C3B—C4B—C5B | −179.45 (17) |
C2A—C3A—C4A—C5A | −0.5 (3) | C2B—C3B—C4B—C5B | 1.7 (3) |
O4A—C4A—C5A—O5A | −1.1 (2) | C3B—C4B—C5B—O5B | 179.22 (17) |
C3A—C4A—C5A—O5A | −176.78 (15) | O4B—C4B—C5B—O5B | −5.0 (3) |
O4A—C4A—C5A—C6A | 177.83 (15) | C3B—C4B—C5B—C6B | −1.5 (3) |
C3A—C4A—C5A—C6A | 2.2 (3) | O4B—C4B—C5B—C6B | 174.30 (17) |
O5A—C5A—C6A—C7A | 177.47 (16) | O5B—C5B—C6B—C7B | 179.61 (16) |
C4A—C5A—C6A—C7A | −1.4 (3) | C4B—C5B—C6B—C7B | 0.4 (3) |
C5A—C6A—C7A—O1A | −179.14 (14) | C5B—C6B—C7B—O1B | −179.77 (15) |
C5A—C6A—C7A—C2A | −1.1 (2) | C5B—C6B—C7B—C2B | 0.5 (3) |
C3A—C2A—C7A—O1A | −179.35 (14) | C3B—C2B—C7B—O1B | −179.97 (15) |
C1A—C2A—C7A—O1A | 3.2 (2) | C1B—C2B—C7B—O1B | 0.7 (3) |
C3A—C2A—C7A—C6A | 2.7 (2) | C3B—C2B—C7B—C6B | −0.2 (3) |
C1A—C2A—C7A—C6A | −174.79 (15) | C1B—C2B—C7B—C6B | −179.56 (17) |
O1A—C8A—C9A—O6A | −175.10 (13) | O1B—C8B—C9B—O6B | 177.72 (15) |
C13A—C8A—C9A—O6A | 3.3 (3) | C13B—C8B—C9B—O6B | −4.1 (3) |
O1A—C8A—C9A—C1A | −0.7 (2) | O1B—C8B—C9B—C1B | −1.5 (3) |
C13A—C8A—C9A—C1A | 177.69 (15) | C13B—C8B—C9B—C1B | 176.64 (16) |
O2A—C1A—C9A—C8A | −175.29 (16) | O2B—C1B—C9B—C8B | 179.95 (18) |
C2A—C1A—C9A—C8A | 3.8 (2) | C2B—C1B—C9B—C8B | −2.1 (3) |
O2A—C1A—C9A—O6A | −0.6 (2) | O2B—C1B—C9B—O6B | 0.7 (3) |
C2A—C1A—C9A—O6A | 178.49 (14) | C2B—C1B—C9B—O6B | 178.63 (15) |
O1A—C8A—C13A—C18A | −2.8 (2) | O1B—C8B—C13B—C18B | 13.3 (2) |
C9A—C8A—C13A—C18A | 178.72 (16) | C9B—C8B—C13B—C18B | −164.99 (17) |
O1A—C8A—C13A—C14A | 175.99 (14) | O1B—C8B—C13B—C14B | −168.81 (15) |
C9A—C8A—C13A—C14A | −2.5 (3) | C9B—C8B—C13B—C14B | 12.9 (3) |
C18A—C13A—C14A—C15A | 1.6 (3) | C18B—C13B—C14B—C15B | 1.0 (3) |
C8A—C13A—C14A—C15A | −177.20 (15) | C8B—C13B—C14B—C15B | −176.89 (16) |
C13A—C14A—C15A—O7A | 179.68 (16) | C13B—C14B—C15B—O7B | 177.03 (16) |
C13A—C14A—C15A—C16A | −0.1 (3) | C13B—C14B—C15B—C16B | −1.8 (3) |
O7A—C15A—C16A—O8A | −1.4 (3) | O7B—C15B—C16B—O8B | −3.1 (2) |
C14A—C15A—C16A—O8A | 178.36 (16) | C14B—C15B—C16B—O8B | 175.83 (16) |
O7A—C15A—C16A—C17A | 178.02 (16) | O7B—C15B—C16B—C17B | −177.78 (16) |
C14A—C15A—C16A—C17A | −2.2 (3) | C14B—C15B—C16B—C17B | 1.1 (3) |
O8A—C16A—C17A—O9A | 1.8 (3) | O8B—C16B—C17B—O9B | 4.5 (3) |
C15A—C16A—C17A—O9A | −177.61 (17) | C15B—C16B—C17B—O9B | 179.23 (17) |
O8A—C16A—C17A—C18A | −177.52 (16) | O8B—C16B—C17B—C18B | −174.38 (17) |
C15A—C16A—C17A—C18A | 3.0 (3) | C15B—C16B—C17B—C18B | 0.3 (3) |
O9A—C17A—C18A—C13A | 179.12 (17) | O9B—C17B—C18B—C13B | −179.96 (17) |
C16A—C17A—C18A—C13A | −1.5 (3) | C16B—C17B—C18B—C13B | −1.1 (3) |
C14A—C13A—C18A—C17A | −0.8 (2) | C14B—C13B—C18B—C17B | 0.5 (3) |
C8A—C13A—C18A—C17A | 178.01 (15) | C8B—C13B—C18B—C17B | 178.41 (16) |
C9A—C8A—O1A—C7A | −1.4 (2) | C9B—C8B—O1B—C7B | 5.0 (2) |
C13A—C8A—O1A—C7A | 179.90 (13) | C13B—C8B—O1B—C7B | −173.49 (14) |
C6A—C7A—O1A—C8A | 178.30 (14) | C6B—C7B—O1B—C8B | 175.69 (15) |
C2A—C7A—O1A—C8A | 0.2 (2) | C2B—C7B—O1B—C8B | −4.6 (2) |
C3A—C4A—O4A—C10A | −109.62 (19) | C3B—C4B—O4B—C10B | −91.9 (3) |
C5A—C4A—O4A—C10A | 74.7 (2) | C5B—C4B—O4B—C10B | 92.3 (3) |
C6A—C5A—O5A—C11A | −3.3 (3) | C6B—C5B—O5B—C11B | −3.4 (3) |
C4A—C5A—O5A—C11A | 175.60 (17) | C4B—C5B—O5B—C11B | 175.89 (18) |
C8A—C9A—O6A—C12A | −108.49 (18) | C8B—C9B—O6B—C12B | 98.1 (2) |
C1A—C9A—O6A—C12A | 76.84 (19) | C1B—C9B—O6B—C12B | −82.6 (2) |
C16A—C15A—O7A—C19A | 174.64 (19) | C14B—C15B—O7B—C19B | −14.0 (3) |
C14A—C15A—O7A—C19A | −5.1 (3) | C16B—C15B—O7B—C19B | 164.84 (17) |
C17A—C16A—O8A—C20A | 106.1 (2) | C15B—C16B—O8B—C20B | 92.9 (2) |
C15A—C16A—O8A—C20A | −74.5 (2) | C17B—C16B—O8B—C20B | −92.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3A—H3A···O2A | 0.82 | 1.91 | 2.6311 (18) | 147 |
O3B—H3B···O2B | 0.82 | 1.87 | 2.603 (2) | 148 |
O9A—H9A···O8A | 0.82 | 2.26 | 2.698 (2) | 114 |
O9B—H9B···O2A | 0.82 | 1.96 | 2.7783 (18) | 176 |
C10A—H10C···O7Ai | 0.96 | 2.57 | 3.495 (2) | 162 |
C14A—H14A···O6A | 0.93 | 2.20 | 2.863 (2) | 128 |
C14B—H14B···O6B | 0.93 | 2.19 | 2.824 (2) | 125 |
C19A—H19C···O5Bii | 0.96 | 2.50 | 3.302 (3) | 141 |
C19B—H19F···Cg1iii | 0.96 | 2.88 | 3.668 | 141 |
Symmetry codes: (i) x+1, y−1, z; (ii) x−1, y+1, z; (iii) −x, −y, −z+2. |
Experimental details
Crystal data |
Chemical formula | C20H20O9 |
Mr | 404.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 273 |
a, b, c (Å) | 7.5629 (5), 15.2199 (9), 17.6543 (11) |
α, β, γ (°) | 69.621 (1), 83.145 (1), 77.760 (1) |
V (Å3) | 1859.3 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.22 × 0.18 × 0.16 |
|
Data collection |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16152, 8323, 6127 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.661 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.131, 1.02 |
No. of reflections | 8323 |
No. of parameters | 537 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.22 |
Selected geometric parameters (Å, º) topC1A—O2A | 1.257 (2) | C1B—O2B | 1.252 (2) |
C3A—O3A | 1.348 (2) | C3B—O3B | 1.352 (2) |
C4A—O4A | 1.371 (2) | C4B—O4B | 1.376 (2) |
C5A—O5A | 1.351 (2) | C5B—O5B | 1.352 (2) |
C7A—O1A | 1.370 (2) | C7B—O1B | 1.366 (2) |
C8A—O1A | 1.362 (2) | C8B—O1B | 1.362 (2) |
C8A—C9A | 1.365 (2) | C8B—C9B | 1.363 (2) |
C9A—O6A | 1.370 (2) | C9B—O6B | 1.366 (2) |
C15A—O7A | 1.357 (2) | C15B—O7B | 1.368 (2) |
C16A—O8A | 1.380 (2) | C16B—O8B | 1.379 (2) |
C17A—O9A | 1.366 (2) | C17B—O9B | 1.360 (2) |
| | | |
C3A—C2A—C1A | 122.31 (15) | C3B—C2B—C1B | 122.32 (16) |
O1A—C7A—C6A | 115.89 (14) | O1B—C7B—C6B | 116.42 (15) |
O1A—C8A—C13A | 110.64 (13) | O1B—C8B—C13B | 111.59 (14) |
C9A—C8A—C13A | 129.39 (15) | C9B—C8B—C13B | 127.96 (16) |
O8A—C16A—C15A | 122.71 (16) | O8B—C16B—C15B | 120.26 (16) |
| | | |
C1A—C2A—C7A—C6A | −174.79 (15) | C9B—C8B—C13B—C18B | −164.99 (17) |
C9A—C8A—C13A—C18A | 178.72 (16) | C3B—C4B—O4B—C10B | −91.9 (3) |
C3A—C4A—O4A—C10A | −109.62 (19) | C6B—C5B—O5B—C11B | −3.4 (3) |
C6A—C5A—O5A—C11A | −3.3 (3) | C1B—C9B—O6B—C12B | −82.6 (2) |
C1A—C9A—O6A—C12A | 76.84 (19) | C14B—C15B—O7B—C19B | −14.0 (3) |
C14A—C15A—O7A—C19A | −5.1 (3) | C17B—C16B—O8B—C20B | −92.5 (2) |
C1B—C2B—C7B—C6B | −179.56 (17) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3A—H3A···O2A | 0.82 | 1.91 | 2.6311 (18) | 146.7 |
O3B—H3B···O2B | 0.82 | 1.87 | 2.603 (2) | 148.0 |
O9A—H9A···O8A | 0.82 | 2.26 | 2.698 (2) | 113.6 |
O9B—H9B···O2A | 0.82 | 1.96 | 2.7783 (18) | 176.1 |
C10A—H10C···O7Ai | 0.96 | 2.57 | 3.495 (2) | 161.6 |
C14A—H14A···O6A | 0.93 | 2.20 | 2.863 (2) | 127.6 |
C14B—H14B···O6B | 0.93 | 2.19 | 2.824 (2) | 124.5 |
C19A—H19C···O5Bii | 0.96 | 2.50 | 3.302 (3) | 140.7 |
C19B—H19F···Cg1iii | 0.96 | 2.88 | 3.668 | 141 |
Symmetry codes: (i) x+1, y−1, z; (ii) x−1, y+1, z; (iii) −x, −y, −z+2. |
Cleome viscosa Linn (Capparaceae) is a bushy and sticky aromatic herb with secretory glandular trichomes (Adams, 1972). This widely distributed herb may have derived from the glandular trichomes [Meaning of sentence not clear - please rephrase]. The ethanolic extracts of the leaves, flowers and stem of this plant have been tested for anti-microbial (Sudhakar et al., 2006), insecticidal and nemeticidal (Williams et al., 2003) activities. The seeds of this plant are said to be anthelmintic and useful in fever, diarrhoea and infantile cunvulsions (Asolkar et al., 1992). As the whole plant, it is useful in treating liver diseases, chronic painful joints and mental disorders (Chatterjee & Pakrashi, 1991). Furthermore, C. Viscosa Linn. has also been studied for its psychopharmacological effects in rat and mouse models (Parimala et al., 2004). In view of the above important properties, the extract of the seeds of this plant has been studied and a number of compounds have been isolated (Mahender, 2006). The title compound, (I), is one of these, and we report its structure here.
In compound (I), two independent molecules, A and B, are present in the asymmetric unit with similar conformations (Fig. 1). The bond lengths and angles show normal values and are comparable with those observed in 5,3'-dihydroxy-3,7,4',5'-tetramethoxyflavone (Etti et al., 2005) and calycopterin (Vijayalakshmi et al., 1986). The geometric parameters in the main skeletons of molecules A and B show no significant differences, but they are distinguished by some bond rotations (Table 1). The dihedral angles between the chromene ring system (C1n–C9n/O1n, n = A or B) and the benzene ring (C13n–C18n) are 4.2 (1) and 12.7 (1)° for molecules A and B, respectively. We understand from the literature (Krishnaiah et al., 2005) that there is a correlation (directly proportional) between the dihedral angle between the benzene ring and the chromene ring system and the C—C bond length joining them. However, this may not necessarily be true, because in (I) the bond length (C8n—C13n) is approximately the same in the two molecules [1.475 (2) Å in A and 1.472 (2) Å in B], despite them having different dihedral angles. Furthermore, Wallet and co-workers (Wallet et al., 1988, 1990; Cody, 1988) reported that there is no relationship between the dihedral angle and the bond distance. The double bonds (C1n—O2n) and the multiple-character bonds (C8n—C9n), which are generally responsible for the photoactivity of coumarins (Song & Gordon, 1970), are confirmed by their respective distances (Table 1). Similarly, the C7n—O1n and C8n—O1n bonds (Table 1) exhibit variation in their distances, a feature quite common in furano compounds and simple coumarins (Rajnikanth et al., 1993; Gupta et al., 1993).
In contrast, some relatively large conformational differences are found in the methoxy substituents. With respect to the chromene ring system, the methoxy substituents at C4n, C5n and C9n make angles of 70.7 (1), 6.3 (1) and 72.9 (1)°, respectively, in molecule A, and 89.5 (2), 3.4 (1), and 80.5 (2)°, respectively, in molecule B. With respect to the benzene ring, the methoxy groups at positions C15n and C16n make angles of 4.7 (1) and 74.5 (1)°, respectively, in A, and 14.8 (1) and 89.8 (1)°, respectively, in B.
Within the asymmetric unit, hydroxy atom O9B attached to the benzene ring acts as hydrogen-bond donor, via atom H9B, to ketone atom O2A attached to the chromene ring system (Fig. 2). In both molecules, the hydroxy atom O3n is involved in an intramolecular hydrogen bond with the adjacent ketone O atom, forming a six-membered pseudo-ring (O2n/C1n/C2n/C3n/O3n/H3n) with an S(6) pattern (Bernstein et al., 1995). Similarly, in molecule A, hydroxy atom O9A is involved in an intramolecular hydrogen bond with methoxy atom O8A, which completes a five-membered pseudo-ring (O8A/C16A/C17A/O9A/H9A) with an S(5) pattern. Similar interactions have been reported in the literature (Smith et al., 2001). Interestingly, the latter interaction is absent in molecule B.
Molecules A in (I) are linked into chains by the co-operative action of a C—H···O hydrogen bond of moderate strength (Table 2). Methyl atom C10A at (x, y, z) acts as hydrogen-bond donor to the methoxy atom O7A at (1 + x, y − 1, z), so forming a C(13) chain (Bernstein et al., 1995) running along the [110] direction (Fig. 2). Each molecule B is linked to two molecules A through O—H···O and C—H···O interactions. The combination of these A and B molecules then generates edge-fused R33(22) rings. Interestingly, only molecules A are involved in aromatic π–π stacking interactions along the a axis. The pyrone rings in the fused chromene ring system are stacked with a centre-to-centre distance of 3.556 Å. In addition, the pyrone ring and the C13A–C18A benzene ring (centroid-to-centroid distance 3.742 Å), and the six-membered C2A–C7A ring in the chromene ring system and the C13A–C18A benzene ring (centroid-to-centroid distance 3.764 Å) are also involved in similar interactions. The structure is further stabilized by weak C—H···π interations (Table 2).