The title compound, C
17H
16O
5, crystallizes with two independent molecules in the asymmetric unit. These are oriented approximately orthogonal to one another. The keto group adopts an
s-
cis conformation; the six-membered ring formed by the O—H

O hydrogen bond and the adjacent benzene ring are approximately coplanar. In addition to an intramolecular O—H

O hydrogen bond, intermolecular O—H

O interactions link adjacent molecules into chains.
Supporting information
CCDC reference: 272110
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.118
- Data-to-parameter ratio = 10.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT410_ALERT_2_C Short Intra H...H Contact H8' .. H11' .. 1.96 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 58.00 A 3
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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
0 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 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: enCIFer (CCDC, 2003) and PARST (Nardelli, 1995).
(
E)-1-(2-hydroxy-3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
top
Crystal data top
C17H16O5 | Z = 4 |
Mr = 300.30 | F(000) = 632 |
Triclinic, P1 | Dx = 1.318 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.6831 (13) Å | Cell parameters from 25 reflections |
b = 11.8477 (13) Å | θ = 1.9–25.0° |
c = 12.9212 (14) Å | µ = 0.10 mm−1 |
α = 111.911 (2)° | T = 293 K |
β = 111.296 (2)° | Prism, yellow |
γ = 92.437 (2)° | 0.25 × 0.25 × 0.13 mm |
V = 1512.9 (3) Å3 | |
Data collection top
Siemens SMART CCD area detector diffractometer | 4667 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
ω scans | h = −13→13 |
14357 measured reflections | k = −14→14 |
5298 independent reflections | l = −15→15 |
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)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0699P)2 + 0.2158P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
5298 reflections | Δρmax = 0.24 e Å−3 |
502 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.025 (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. |
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 basedon 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 | |
H8' | 0.4238 (15) | 0.1300 (15) | 0.4727 (15) | 0.057 (4)* | |
H5 | 0.5515 (15) | 1.1255 (14) | 0.9027 (14) | 0.050 (4)* | |
H11' | 0.5620 (16) | 0.2444 (15) | 0.6258 (14) | 0.058 (4)* | |
H16A | 0.353 (2) | 0.342 (2) | 0.812 (2) | 0.091 (7)* | |
H30' | 0.748 (2) | 0.0775 (19) | 0.3801 (19) | 0.086 (6)* | |
H12' | 0.7127 (15) | 0.4088 (15) | 0.7894 (15) | 0.057 (4)* | |
H7' | 0.3561 (17) | −0.0579 (17) | 0.2443 (17) | 0.072 (5)* | |
H6' | 0.0225 (16) | 0.0537 (16) | 0.4318 (17) | 0.065 (5)* | |
H16B | 0.250 (3) | 0.285 (2) | 0.682 (2) | 0.105 (8)* | |
H6 | 0.6021 (16) | 1.3339 (15) | 0.9462 (15) | 0.062 (5)* | |
H5' | 0.2331 (16) | 0.0981 (16) | 0.4639 (16) | 0.062 (4)* | |
H3' | 0.1399 (18) | −0.1514 (18) | 0.1169 (18) | 0.080 (6)* | |
H16C | 0.3471 (19) | 0.203 (2) | 0.7290 (18) | 0.088 (6)* | |
H2' | −0.0682 (19) | −0.1925 (19) | 0.0867 (19) | 0.084 (6)* | |
H12 | 0.3329 (17) | 0.5838 (16) | 0.5177 (17) | 0.068 (5)* | |
H2 | 0.9127 (18) | 1.3793 (18) | 1.2438 (18) | 0.075 (5)* | |
H8 | 0.5423 (15) | 0.9107 (14) | 0.8581 (15) | 0.054 (4)* | |
H10' | −0.210 (2) | −0.1510 (19) | 0.169 (2) | 0.080 (6)* | |
H7 | 0.735 (2) | 0.9755 (19) | 1.0845 (19) | 0.082 (6)* | |
H3 | 0.8621 (19) | 1.1705 (19) | 1.1998 (18) | 0.084 (6)* | |
H30 | 0.612 (2) | 0.599 (2) | 0.9573 (19) | 0.084 (6)* | |
H11 | 0.4510 (17) | 0.7591 (18) | 0.6936 (16) | 0.072 (5)* | |
H10 | 0.858 (2) | 1.5282 (18) | 1.1771 (19) | 0.075 (6)* | |
H17A | 0.316 (3) | 0.391 (3) | 0.361 (3) | 0.129 (10)* | |
H17C | 0.205 (2) | 0.268 (2) | 0.315 (2) | 0.104 (7)* | |
H17B | 0.181 (3) | 0.407 (3) | 0.370 (2) | 0.128 (10)* | |
O4B | 0.81864 (9) | 0.13960 (9) | 0.43893 (9) | 0.0514 (3) | |
O4A | 0.56505 (10) | 0.52184 (10) | 0.89926 (10) | 0.0555 (3) | |
O5B | 0.58986 (9) | 0.01706 (9) | 0.33105 (9) | 0.0574 (3) | |
O5A | 0.66468 (10) | 0.75337 (9) | 1.00635 (9) | 0.0590 (3) | |
O3B | 0.99764 (9) | 0.33500 (10) | 0.63751 (9) | 0.0561 (3) | |
O3A | 0.42074 (10) | 0.32499 (8) | 0.69194 (10) | 0.0523 (3) | |
O1B | −0.16175 (9) | −0.09641 (10) | 0.24611 (11) | 0.0565 (3) | |
C2'' | 0.78607 (12) | 0.20946 (11) | 0.52819 (12) | 0.0399 (3) | |
C1'' | 0.66422 (12) | 0.18679 (12) | 0.52408 (12) | 0.0408 (3) | |
O1A | 0.79011 (11) | 1.49682 (10) | 1.11591 (12) | 0.0649 (3) | |
C3'' | 0.87705 (12) | 0.30951 (12) | 0.62784 (12) | 0.0430 (3) | |
C2' | 0.50193 (12) | 0.54449 (12) | 0.80181 (12) | 0.0425 (3) | |
C3' | 0.42508 (12) | 0.44209 (12) | 0.69486 (13) | 0.0438 (3) | |
C8A | 0.59956 (14) | 0.89845 (13) | 0.92402 (14) | 0.0494 (3) | |
C6'' | 0.64155 (13) | 0.26178 (14) | 0.62381 (13) | 0.0498 (3) | |
C1' | 0.51258 (13) | 0.66513 (12) | 0.80428 (13) | 0.0453 (3) | |
C2A | 0.62663 (13) | 1.17616 (12) | 0.97245 (12) | 0.0451 (3) | |
C9A | 0.59565 (13) | 0.77173 (12) | 0.91638 (13) | 0.0466 (3) | |
C2B | 0.17049 (13) | 0.03618 (14) | 0.38509 (13) | 0.0500 (3) | |
C8B | 0.43588 (12) | 0.07687 (13) | 0.40661 (14) | 0.0470 (3) | |
C4B | −0.04143 (12) | −0.07427 (12) | 0.25752 (13) | 0.0446 (3) | |
O2B | 0.94290 (10) | 0.47966 (11) | 0.81543 (10) | 0.0672 (3) | |
C9B | 0.56524 (12) | 0.08740 (12) | 0.41557 (12) | 0.0427 (3) | |
O2A | 0.29525 (11) | 0.34961 (9) | 0.48814 (10) | 0.0662 (3) | |
C3A | 0.65597 (13) | 1.29971 (13) | 0.99703 (14) | 0.0483 (3) | |
C4'' | 0.84834 (13) | 0.38370 (13) | 0.72369 (13) | 0.0485 (3) | |
C1B | 0.20934 (12) | −0.02494 (13) | 0.29279 (12) | 0.0463 (3) | |
C3B | 0.04733 (13) | 0.01236 (14) | 0.36842 (13) | 0.0511 (3) | |
C4A | 0.76404 (13) | 1.37618 (12) | 1.09712 (13) | 0.0498 (3) | |
C4' | 0.36294 (14) | 0.45639 (13) | 0.58791 (13) | 0.0507 (3) | |
C5'' | 0.73100 (14) | 0.35860 (15) | 0.72309 (14) | 0.0542 (4) | |
C6' | 0.44453 (16) | 0.67546 (14) | 0.69509 (14) | 0.0591 (4) | |
C7B | 0.34015 (13) | −0.00582 (14) | 0.30982 (14) | 0.0509 (3) | |
C1A | 0.70377 (15) | 1.12490 (13) | 1.04545 (13) | 0.0538 (4) | |
C5B | −0.00588 (15) | −0.13434 (17) | 0.16430 (15) | 0.0668 (5) | |
C5' | 0.37259 (17) | 0.57430 (15) | 0.58852 (15) | 0.0634 (4) | |
C7A | 0.68259 (17) | 0.99392 (14) | 1.02086 (16) | 0.0620 (4) | |
C6B | 0.11796 (15) | −0.11036 (18) | 0.18185 (16) | 0.0691 (5) | |
C10A | 0.33669 (18) | 0.28699 (16) | 0.7341 (2) | 0.0605 (4) | |
C5A | 0.84008 (17) | 1.32817 (15) | 1.17280 (16) | 0.0699 (5) | |
C6A | 0.81015 (19) | 1.20420 (16) | 1.14713 (17) | 0.0760 (6) | |
C10B | 1.00922 (17) | 0.36184 (18) | 0.54291 (17) | 0.0726 (5) | |
H33A | 1.0963 | 0.3782 | 0.5579 | 0.109* | |
H33B | 0.9746 | 0.4335 | 0.5412 | 0.109* | |
H33C | 0.9646 | 0.2919 | 0.4657 | 0.109* | |
C11B | 0.91473 (19) | 0.56961 (18) | 0.90748 (17) | 0.0826 (6) | |
H34A | 0.9892 | 0.6316 | 0.9661 | 0.124* | |
H34B | 0.8847 | 0.5296 | 0.9478 | 0.124* | |
H34C | 0.8513 | 0.6083 | 0.8706 | 0.124* | |
C11A | 0.2435 (3) | 0.3540 (2) | 0.37230 (18) | 0.0892 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4B | 0.0423 (5) | 0.0498 (6) | 0.0527 (6) | 0.0038 (4) | 0.0246 (5) | 0.0073 (4) |
O4A | 0.0646 (7) | 0.0442 (6) | 0.0546 (6) | 0.0098 (5) | 0.0156 (5) | 0.0262 (5) |
O5B | 0.0445 (5) | 0.0519 (6) | 0.0578 (6) | 0.0020 (4) | 0.0217 (5) | 0.0045 (5) |
O5A | 0.0598 (6) | 0.0465 (6) | 0.0552 (6) | 0.0009 (5) | 0.0065 (5) | 0.0228 (5) |
O3B | 0.0359 (5) | 0.0653 (6) | 0.0596 (6) | 0.0009 (4) | 0.0193 (4) | 0.0194 (5) |
O3A | 0.0618 (6) | 0.0347 (5) | 0.0753 (7) | 0.0136 (4) | 0.0425 (5) | 0.0240 (5) |
O1B | 0.0365 (5) | 0.0630 (7) | 0.0592 (7) | −0.0003 (5) | 0.0177 (5) | 0.0175 (5) |
C2'' | 0.0380 (6) | 0.0382 (6) | 0.0449 (7) | 0.0093 (5) | 0.0185 (5) | 0.0170 (5) |
C1'' | 0.0357 (6) | 0.0393 (6) | 0.0483 (7) | 0.0079 (5) | 0.0175 (6) | 0.0189 (6) |
O1A | 0.0507 (6) | 0.0382 (5) | 0.0845 (8) | 0.0004 (5) | 0.0114 (6) | 0.0205 (5) |
C3'' | 0.0334 (6) | 0.0451 (7) | 0.0477 (7) | 0.0058 (5) | 0.0153 (5) | 0.0182 (6) |
C2' | 0.0424 (7) | 0.0406 (7) | 0.0502 (7) | 0.0111 (5) | 0.0217 (6) | 0.0218 (6) |
C3' | 0.0453 (7) | 0.0350 (6) | 0.0572 (8) | 0.0102 (5) | 0.0270 (6) | 0.0195 (6) |
C8A | 0.0514 (8) | 0.0395 (7) | 0.0529 (8) | 0.0049 (6) | 0.0174 (7) | 0.0190 (6) |
C6'' | 0.0392 (7) | 0.0521 (8) | 0.0564 (8) | 0.0078 (6) | 0.0241 (6) | 0.0166 (6) |
C1' | 0.0465 (7) | 0.0376 (7) | 0.0510 (7) | 0.0068 (5) | 0.0174 (6) | 0.0202 (6) |
C2A | 0.0416 (7) | 0.0396 (7) | 0.0445 (7) | 0.0014 (5) | 0.0154 (6) | 0.0106 (6) |
C9A | 0.0447 (7) | 0.0427 (7) | 0.0512 (8) | 0.0049 (6) | 0.0176 (6) | 0.0208 (6) |
C2B | 0.0392 (7) | 0.0534 (8) | 0.0425 (7) | 0.0005 (6) | 0.0115 (6) | 0.0109 (6) |
C8B | 0.0387 (7) | 0.0457 (7) | 0.0532 (8) | 0.0054 (6) | 0.0187 (6) | 0.0175 (6) |
C4B | 0.0361 (6) | 0.0440 (7) | 0.0516 (7) | 0.0045 (5) | 0.0159 (6) | 0.0203 (6) |
O2B | 0.0499 (6) | 0.0619 (7) | 0.0559 (6) | −0.0052 (5) | 0.0161 (5) | −0.0031 (5) |
C9B | 0.0401 (7) | 0.0382 (7) | 0.0505 (7) | 0.0071 (5) | 0.0185 (6) | 0.0192 (6) |
O2A | 0.0768 (8) | 0.0436 (6) | 0.0550 (6) | −0.0014 (5) | 0.0140 (5) | 0.0104 (5) |
C3A | 0.0429 (7) | 0.0428 (7) | 0.0552 (8) | 0.0087 (6) | 0.0176 (6) | 0.0189 (6) |
C4'' | 0.0420 (7) | 0.0461 (7) | 0.0454 (7) | 0.0042 (6) | 0.0129 (6) | 0.0120 (6) |
C1B | 0.0374 (7) | 0.0468 (7) | 0.0469 (7) | 0.0024 (6) | 0.0150 (6) | 0.0143 (6) |
C3B | 0.0434 (7) | 0.0575 (8) | 0.0458 (8) | 0.0071 (6) | 0.0194 (6) | 0.0142 (7) |
C4A | 0.0470 (7) | 0.0355 (7) | 0.0592 (8) | 0.0030 (6) | 0.0205 (6) | 0.0137 (6) |
C4' | 0.0493 (8) | 0.0396 (7) | 0.0527 (8) | 0.0038 (6) | 0.0164 (6) | 0.0133 (6) |
C5'' | 0.0482 (8) | 0.0564 (9) | 0.0504 (8) | 0.0102 (7) | 0.0243 (7) | 0.0105 (7) |
C6' | 0.0710 (10) | 0.0388 (8) | 0.0564 (9) | 0.0045 (7) | 0.0112 (7) | 0.0235 (7) |
C7B | 0.0421 (7) | 0.0535 (8) | 0.0509 (8) | 0.0044 (6) | 0.0202 (6) | 0.0151 (7) |
C1A | 0.0586 (9) | 0.0407 (7) | 0.0493 (8) | −0.0008 (6) | 0.0127 (7) | 0.0159 (6) |
C5B | 0.0414 (8) | 0.0682 (10) | 0.0539 (9) | −0.0065 (7) | 0.0136 (7) | −0.0049 (8) |
C5' | 0.0747 (11) | 0.0475 (8) | 0.0521 (9) | 0.0053 (7) | 0.0074 (8) | 0.0231 (7) |
C7A | 0.0659 (10) | 0.0446 (8) | 0.0609 (9) | 0.0007 (7) | 0.0091 (8) | 0.0242 (7) |
C6B | 0.0460 (8) | 0.0789 (11) | 0.0521 (9) | −0.0009 (8) | 0.0218 (7) | −0.0038 (8) |
C10A | 0.0671 (11) | 0.0498 (9) | 0.0817 (12) | 0.0111 (8) | 0.0445 (10) | 0.0313 (9) |
C5A | 0.0659 (10) | 0.0458 (8) | 0.0620 (10) | −0.0091 (7) | −0.0036 (8) | 0.0164 (7) |
C6A | 0.0784 (12) | 0.0506 (9) | 0.0648 (10) | −0.0040 (8) | −0.0079 (9) | 0.0268 (8) |
C10B | 0.0637 (10) | 0.0757 (11) | 0.0774 (11) | −0.0085 (8) | 0.0358 (9) | 0.0267 (9) |
C11B | 0.0745 (12) | 0.0713 (12) | 0.0598 (10) | 0.0029 (9) | 0.0210 (9) | −0.0084 (9) |
C11A | 0.1093 (19) | 0.0651 (12) | 0.0537 (11) | 0.0013 (13) | 0.0067 (11) | 0.0117 (9) |
Geometric parameters (Å, º) top
O4B—C2'' | 1.3391 (16) | C4B—C3B | 1.384 (2) |
O4B—H30' | 0.93 (2) | O2B—C4'' | 1.3617 (17) |
O4A—C2' | 1.3401 (16) | O2B—C11B | 1.424 (2) |
O4A—H30 | 0.92 (2) | O2A—C4' | 1.3583 (17) |
O5B—C9B | 1.2406 (17) | O2A—C11A | 1.418 (2) |
O5A—C9A | 1.2538 (17) | C3A—C4A | 1.389 (2) |
O3B—C3'' | 1.3782 (15) | C3A—H6 | 0.956 (17) |
O3B—C10B | 1.421 (2) | C4''—C5'' | 1.387 (2) |
O3A—C3' | 1.3720 (15) | C1B—C6B | 1.390 (2) |
O3A—C10A | 1.4133 (18) | C1B—C7B | 1.4575 (19) |
O1B—C4B | 1.3622 (16) | C3B—H6' | 0.939 (19) |
O1B—H10' | 0.90 (2) | C4A—C5A | 1.377 (2) |
C2''—C3'' | 1.3973 (18) | C4'—C5' | 1.394 (2) |
C2''—C1'' | 1.4154 (17) | C5''—H12' | 0.948 (17) |
C1''—C6'' | 1.3905 (19) | C6'—C5' | 1.371 (2) |
C1''—C9B | 1.4711 (18) | C6'—H11 | 0.998 (19) |
O1A—C4A | 1.3583 (17) | C7B—H7' | 0.931 (19) |
O1A—H10 | 0.83 (2) | C1A—C6A | 1.395 (2) |
C3''—C4'' | 1.391 (2) | C1A—C7A | 1.453 (2) |
C2'—C3' | 1.3938 (19) | C5B—C6B | 1.380 (2) |
C2'—C1' | 1.4169 (18) | C5B—H2' | 0.96 (2) |
C3'—C4' | 1.386 (2) | C5'—H12 | 0.915 (19) |
C8A—C7A | 1.325 (2) | C7A—H7 | 0.94 (2) |
C8A—C9A | 1.4650 (19) | C6B—H3' | 0.93 (2) |
C8A—H8 | 0.939 (17) | C10A—H16A | 0.91 (2) |
C6''—C5'' | 1.371 (2) | C10A—H16B | 0.99 (3) |
C6''—H11' | 0.955 (17) | C10A—H16C | 0.99 (2) |
C1'—C6' | 1.400 (2) | C5A—C6A | 1.378 (2) |
C1'—C9A | 1.4644 (19) | C5A—H2 | 0.95 (2) |
C2A—C3A | 1.3755 (19) | C6A—H3 | 0.96 (2) |
C2A—C1A | 1.388 (2) | C10B—H33A | 0.9600 |
C2A—H5 | 0.959 (16) | C10B—H33B | 0.9600 |
C2B—C3B | 1.375 (2) | C10B—H33C | 0.9600 |
C2B—C1B | 1.389 (2) | C11B—H34A | 0.9600 |
C2B—H5' | 0.983 (17) | C11B—H34B | 0.9600 |
C8B—C7B | 1.323 (2) | C11B—H34C | 0.9600 |
C8B—C9B | 1.4693 (18) | C11A—H17A | 1.02 (3) |
C8B—H8' | 0.917 (17) | C11A—H17C | 0.97 (3) |
C4B—C5B | 1.371 (2) | C11A—H17B | 0.98 (3) |
| | | |
C2''—O4B—H30' | 107.0 (13) | C4B—C3B—H6' | 119.2 (11) |
C2'—O4A—H30 | 103.2 (13) | O1A—C4A—C5A | 122.62 (13) |
C3''—O3B—C10B | 115.89 (12) | O1A—C4A—C3A | 117.75 (13) |
C3'—O3A—C10A | 116.56 (11) | C5A—C4A—C3A | 119.63 (13) |
C4B—O1B—H10' | 108.3 (13) | O2A—C4'—C3' | 115.15 (12) |
O4B—C2''—C3'' | 117.65 (11) | O2A—C4'—C5' | 124.89 (14) |
O4B—C2''—C1'' | 122.73 (11) | C3'—C4'—C5' | 119.96 (13) |
C3''—C2''—C1'' | 119.61 (11) | C6''—C5''—C4'' | 118.81 (13) |
C6''—C1''—C2'' | 118.16 (12) | C6''—C5''—H12' | 120.8 (10) |
C6''—C1''—C9B | 121.83 (12) | C4''—C5''—H12' | 120.4 (10) |
C2''—C1''—C9B | 120.01 (11) | C5'—C6'—C1' | 122.51 (13) |
C4A—O1A—H10 | 105.4 (14) | C5'—C6'—H11 | 118.5 (10) |
O3B—C3''—C4'' | 118.00 (12) | C1'—C6'—H11 | 119.0 (11) |
O3B—C3''—C2'' | 122.14 (12) | C8B—C7B—C1B | 127.06 (14) |
C4''—C3''—C2'' | 119.81 (12) | C8B—C7B—H7' | 117.9 (12) |
O4A—C2'—C3' | 116.61 (11) | C1B—C7B—H7' | 115.0 (12) |
O4A—C2'—C1' | 122.81 (12) | C2A—C1A—C6A | 117.55 (13) |
C3'—C2'—C1' | 120.57 (12) | C2A—C1A—C7A | 124.26 (13) |
O3A—C3'—C4' | 119.52 (12) | C6A—C1A—C7A | 118.17 (14) |
O3A—C3'—C2' | 119.96 (12) | C4B—C5B—C6B | 120.19 (14) |
C4'—C3'—C2' | 120.19 (12) | C4B—C5B—H2' | 119.3 (12) |
C7A—C8A—C9A | 121.14 (14) | C6B—C5B—H2' | 120.5 (12) |
C7A—C8A—H8 | 120.4 (10) | C6'—C5'—C4' | 119.60 (14) |
C9A—C8A—H8 | 118.5 (10) | C6'—C5'—H12 | 120.2 (11) |
C5''—C6''—C1'' | 122.57 (13) | C4'—C5'—H12 | 120.1 (11) |
C5''—C6''—H11' | 117.7 (10) | C8A—C7A—C1A | 129.86 (15) |
C1''—C6''—H11' | 119.7 (10) | C8A—C7A—H7 | 116.0 (13) |
C6'—C1'—C2' | 117.07 (12) | C1A—C7A—H7 | 114.1 (13) |
C6'—C1'—C9A | 122.74 (12) | C5B—C6B—C1B | 121.53 (15) |
C2'—C1'—C9A | 120.15 (12) | C5B—C6B—H3' | 118.8 (12) |
C3A—C2A—C1A | 121.31 (13) | C1B—C6B—H3' | 119.7 (12) |
C3A—C2A—H5 | 118.3 (9) | O3A—C10A—H16A | 110.6 (14) |
C1A—C2A—H5 | 120.4 (9) | O3A—C10A—H16B | 109.2 (14) |
O5A—C9A—C1' | 119.11 (12) | H16A—C10A—H16B | 107.5 (19) |
O5A—C9A—C8A | 119.97 (12) | O3A—C10A—H16C | 106.5 (12) |
C1'—C9A—C8A | 120.92 (12) | H16A—C10A—H16C | 112.1 (18) |
C3B—C2B—C1B | 121.64 (13) | H16B—C10A—H16C | 110.9 (18) |
C3B—C2B—H5' | 119.7 (10) | C4A—C5A—C6A | 119.85 (15) |
C1B—C2B—H5' | 118.7 (10) | C4A—C5A—H2 | 121.3 (12) |
C7B—C8B—C9B | 122.84 (14) | C6A—C5A—H2 | 118.9 (11) |
C7B—C8B—H8' | 120.4 (10) | C5A—C6A—C1A | 121.55 (16) |
C9B—C8B—H8' | 116.7 (10) | C5A—C6A—H3 | 120.3 (13) |
O1B—C4B—C5B | 122.64 (13) | C1A—C6A—H3 | 118.2 (13) |
O1B—C4B—C3B | 117.88 (12) | O3B—C10B—H33A | 109.5 |
C5B—C4B—C3B | 119.47 (13) | O3B—C10B—H33B | 109.5 |
C4''—O2B—C11B | 118.07 (13) | H33A—C10B—H33B | 109.5 |
O5B—C9B—C8B | 120.69 (12) | O3B—C10B—H33C | 109.5 |
O5B—C9B—C1'' | 120.46 (11) | H33A—C10B—H33C | 109.5 |
C8B—C9B—C1'' | 118.79 (12) | H33B—C10B—H33C | 109.5 |
C4'—O2A—C11A | 118.41 (14) | O2B—C11B—H34A | 109.5 |
C2A—C3A—C4A | 120.07 (14) | O2B—C11B—H34B | 109.5 |
C2A—C3A—H6 | 120.5 (10) | H34A—C11B—H34B | 109.5 |
C4A—C3A—H6 | 119.4 (10) | O2B—C11B—H34C | 109.5 |
O2B—C4''—C5'' | 123.90 (13) | H34A—C11B—H34C | 109.5 |
O2B—C4''—C3'' | 115.16 (12) | H34B—C11B—H34C | 109.5 |
C5''—C4''—C3'' | 120.94 (13) | O2A—C11A—H17A | 106.6 (16) |
C2B—C1B—C6B | 117.13 (13) | O2A—C11A—H17C | 104.0 (14) |
C2B—C1B—C7B | 122.77 (12) | H17A—C11A—H17C | 114 (2) |
C6B—C1B—C7B | 120.06 (13) | O2A—C11A—H17B | 110.2 (16) |
C2B—C3B—C4B | 120.02 (13) | H17A—C11A—H17B | 110 (2) |
C2B—C3B—H6' | 120.8 (11) | H17C—C11A—H17B | 111 (2) |
| | | |
O4B—C2''—C1''—C6'' | 177.44 (12) | C2''—C3''—C4''—C5'' | 1.2 (2) |
C3''—C2''—C1''—C6'' | −3.52 (19) | C3B—C2B—C1B—C6B | 0.8 (2) |
O4B—C2''—C1''—C9B | −3.48 (19) | C3B—C2B—C1B—C7B | −177.02 (14) |
C3''—C2''—C1''—C9B | 175.55 (11) | C1B—C2B—C3B—C4B | −0.1 (2) |
C10B—O3B—C3''—C4'' | −121.96 (15) | O1B—C4B—C3B—C2B | 178.78 (13) |
C10B—O3B—C3''—C2'' | 60.76 (18) | C5B—C4B—C3B—C2B | −1.0 (2) |
O4B—C2''—C3''—O3B | −1.82 (19) | C2A—C3A—C4A—O1A | 178.65 (13) |
C1''—C2''—C3''—O3B | 179.09 (12) | C2A—C3A—C4A—C5A | −1.3 (2) |
O4B—C2''—C3''—C4'' | −179.05 (12) | C11A—O2A—C4'—C3' | −171.33 (19) |
C1''—C2''—C3''—C4'' | 1.87 (19) | C11A—O2A—C4'—C5' | 8.8 (3) |
C10A—O3A—C3'—C4' | −101.61 (17) | O3A—C3'—C4'—O2A | 3.76 (19) |
C10A—O3A—C3'—C2' | 84.99 (17) | C2'—C3'—C4'—O2A | 177.15 (12) |
O4A—C2'—C3'—O3A | −2.47 (18) | O3A—C3'—C4'—C5' | −176.39 (14) |
C1'—C2'—C3'—O3A | 176.56 (11) | C2'—C3'—C4'—C5' | −3.0 (2) |
O4A—C2'—C3'—C4' | −175.83 (12) | C1''—C6''—C5''—C4'' | 0.7 (2) |
C1'—C2'—C3'—C4' | 3.2 (2) | O2B—C4''—C5''—C6'' | 177.86 (14) |
C2''—C1''—C6''—C5'' | 2.3 (2) | C3''—C4''—C5''—C6'' | −2.5 (2) |
C9B—C1''—C6''—C5'' | −176.78 (13) | C2'—C1'—C6'—C5' | −1.6 (2) |
O4A—C2'—C1'—C6' | 178.05 (13) | C9A—C1'—C6'—C5' | 176.10 (16) |
C3'—C2'—C1'—C6' | −0.9 (2) | C9B—C8B—C7B—C1B | 179.01 (13) |
O4A—C2'—C1'—C9A | 0.3 (2) | C2B—C1B—C7B—C8B | −6.7 (3) |
C3'—C2'—C1'—C9A | −178.69 (12) | C6B—C1B—C7B—C8B | 175.54 (17) |
C6'—C1'—C9A—O5A | −171.72 (15) | C3A—C2A—C1A—C6A | 2.1 (2) |
C2'—C1'—C9A—O5A | 5.9 (2) | C3A—C2A—C1A—C7A | −176.20 (15) |
C6'—C1'—C9A—C8A | 7.8 (2) | O1B—C4B—C5B—C6B | −178.49 (16) |
C2'—C1'—C9A—C8A | −174.55 (12) | C3B—C4B—C5B—C6B | 1.3 (3) |
C7A—C8A—C9A—O5A | 5.8 (2) | C1'—C6'—C5'—C4' | 1.8 (3) |
C7A—C8A—C9A—C1' | −173.69 (15) | O2A—C4'—C5'—C6' | −179.64 (16) |
C7B—C8B—C9B—O5B | −0.4 (2) | C3'—C4'—C5'—C6' | 0.5 (3) |
C7B—C8B—C9B—C1'' | 176.69 (13) | C9A—C8A—C7A—C1A | 178.67 (16) |
C6''—C1''—C9B—O5B | −175.65 (13) | C2A—C1A—C7A—C8A | 7.8 (3) |
C2''—C1''—C9B—O5B | 5.31 (19) | C6A—C1A—C7A—C8A | −170.5 (2) |
C6''—C1''—C9B—C8B | 7.24 (19) | C4B—C5B—C6B—C1B | −0.5 (3) |
C2''—C1''—C9B—C8B | −171.80 (12) | C2B—C1B—C6B—C5B | −0.5 (3) |
C1A—C2A—C3A—C4A | −0.6 (2) | C7B—C1B—C6B—C5B | 177.36 (17) |
C11B—O2B—C4''—C5'' | −9.2 (2) | O1A—C4A—C5A—C6A | −178.39 (18) |
C11B—O2B—C4''—C3'' | 171.09 (16) | C3A—C4A—C5A—C6A | 1.6 (3) |
O3B—C3''—C4''—O2B | 3.53 (19) | C4A—C5A—C6A—C1A | 0.0 (3) |
C2''—C3''—C4''—O2B | −179.13 (12) | C2A—C1A—C6A—C5A | −1.8 (3) |
O3B—C3''—C4''—C5'' | −176.17 (13) | C7A—C1A—C6A—C5A | 176.6 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4A—H30···O5A | 0.92 (2) | 1.70 (3) | 2.5534 (17) | 153 (2) |
O4B—H30′···O5B | 0.94 (2) | 1.74 (2) | 2.5784 (16) | 147 (2) |
O1A—H10···O3Bi | 0.83 (2) | 2.27 (2) | 3.0616 (17) | 160 (2) |
O1A—H10···O2Bi | 0.83 (2) | 2.30 (3) | 2.8855 (19) | 128 (2) |
O1B—H10′···O5Aii | 0.90 (2) | 1.92 (2) | 2.8093 (16) | 169 (2) |
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) x−1, y−1, z−1. |