Structural changes that occur during the [2 + 2] photodimerization of the metastable α′-polymorph of
ortho-ethoxy-
trans-cinnamic acid at 293 K are presented here. Crystals of the α′-polymorph were first stabilized by exposing the α-polymorph to UV light for a short period of time at 343 K. The photodimerization reaction was then carried out at 293 K and observed
in situ by single-crystal X-ray diffraction. The α′-polymorph contains three molecules in the asymmetric unit, labelled
A,
B and
C, which are arranged to form two potential reaction sites. The intermolecular distance between the C=C bonds of molecules
A and
B (making up the
AB site) is 3.6 Å, and these were observed to undergo photodimerization at 293 K. The corresponding distance between centrosymmetrically related C=C bonds in the
CC site (made up of
C molecules) is 4.6 Å, and these remain unreacted even after 60 h irradiation at 293 K. The crystal of the final product, which corresponds to a 66.7% conversion (only two out of three molecules in the asymmetric unit take part in the photodimerization reaction at 293 K), contains an ordered arrangement of the photodimer and unreacted monomer. The crystal retains many structural features of the original monomer crystal, including carboxylic acid hydrogen bonds and C—H
O interactions. Single-crystal X-ray diffraction was used to monitor changes in the unit-cell parameters, reacting molecules and molecular conformations as the reaction progressed. The conformation of the photodimer obtained from the solid-state reaction differs from that of the photodimer obtained by recrystallization from solution.
Supporting information
CCDC references: 241458; 241459; 241460; 241461; 241462
For all compounds, data collection: Bruker SMART; cell refinement: Bruker SMART; data reduction: Bruker SHELXTL; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.
(d6hlt_s) (
E)-3-(2-Ethoxyphenyl)propenoic acid and
trans-2,4-bis(2-ethoxyphenyl)-
trans-1,3-cyclobutane-dicarboxylic acid
top
Crystal data top
0.124(C22H24O6)·2.752(C11H12O3) | Z = 2 |
Mr = 576.62 | F(000) = 612 |
Triclinic, P1 | Dx = 1.283 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 8.6452 (13) Å | Cell parameters from 728 reflections |
b = 10.8577 (17) Å | θ = 2.4–26.3° |
c = 17.262 (3) Å | µ = 0.09 mm−1 |
α = 92.470 (3)° | T = 173 K |
β = 92.102 (3)° | Irregular, white |
γ = 112.563 (3)° | 0.38 × 0.33 × 0.24 mm |
V = 1492.4 (4) Å3 | |
Data collection top
CCD area detector diffractometer | 3167 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 25.5°, θmin = 1.2° |
phi and ω scans | h = −10→8 |
8177 measured reflections | k = −13→13 |
5500 independent reflections | l = −20→20 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0572P)2 + 0.0749P] where P = (Fo2 + 2Fc2)/3 |
5500 reflections | (Δ/σ)max < 0.001 |
390 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Crystal data top
0.124(C22H24O6)·2.752(C11H12O3) | γ = 112.563 (3)° |
Mr = 576.62 | V = 1492.4 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.6452 (13) Å | Mo Kα radiation |
b = 10.8577 (17) Å | µ = 0.09 mm−1 |
c = 17.262 (3) Å | T = 173 K |
α = 92.470 (3)° | 0.38 × 0.33 × 0.24 mm |
β = 92.102 (3)° | |
Data collection top
CCD area detector diffractometer | 3167 reflections with I > 2σ(I) |
8177 measured reflections | Rint = 0.022 |
5500 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.14 e Å−3 |
5500 reflections | Δρmin = −0.21 e Å−3 |
390 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 | Occ. (<1) |
C1A | 1.0162 (3) | 0.0296 (2) | 0.22157 (15) | 0.0409 (7) | 0.876 (2) |
C2A | 1.0094 (4) | 0.0241 (3) | 0.30238 (15) | 0.0419 (7) | 0.876 (2) |
C3A | 1.1499 (4) | 0.0338 (3) | 0.34793 (17) | 0.0495 (8) | 0.876 (2) |
H3A | 1.1454 | 0.0318 | 0.4028 | 0.059* | 0.876 (2) |
C4A | 1.2960 (4) | 0.0462 (3) | 0.31332 (19) | 0.0562 (8) | 0.876 (2) |
H4A | 1.3916 | 0.0519 | 0.3445 | 0.067* | 0.876 (2) |
C5A | 1.3042 (4) | 0.0504 (3) | 0.2336 (2) | 0.0578 (8) | 0.876 (2) |
H5A | 1.4053 | 0.0595 | 0.2100 | 0.069* | 0.876 (2) |
C6A | 1.1662 (4) | 0.0414 (3) | 0.18871 (17) | 0.0511 (8) | 0.876 (2) |
H6A | 1.1725 | 0.0432 | 0.1339 | 0.061* | 0.876 (2) |
C11A | 0.8669 (3) | 0.0204 (2) | 0.17418 (14) | 0.0431 (7) | 0.876 (2) |
H11A | 0.7711 | 0.0140 | 0.2016 | 0.052* | 0.876 (2) |
C12A | 0.8511 (4) | 0.0198 (2) | 0.09700 (14) | 0.0458 (7) | 0.876 (2) |
H12A | 0.9449 | 0.0270 | 0.0678 | 0.055* | 0.876 (2) |
C13A | 0.6963 (4) | 0.0087 (2) | 0.05566 (15) | 0.0453 (7) | 0.876 (2) |
C21A | 0.8459 (4) | 0.0094 (3) | 0.41466 (14) | 0.0461 (7) | 0.876 (2) |
H21C | 0.9338 | 0.0898 | 0.4412 | 0.055* | 0.876 (2) |
H21D | 0.8592 | −0.0708 | 0.4338 | 0.055* | 0.876 (2) |
C22A | 0.6753 (4) | 0.0064 (3) | 0.43047 (16) | 0.0522 (8) | 0.876 (2) |
H22D | 0.6661 | 0.0886 | 0.4139 | 0.078* | 0.876 (2) |
H22E | 0.6586 | −0.0005 | 0.4862 | 0.078* | 0.876 (2) |
H22F | 0.5897 | −0.0709 | 0.4016 | 0.078* | 0.876 (2) |
O11A | 0.6924 (2) | 0.01017 (19) | −0.01746 (11) | 0.0515 (6) | 0.876 (2) |
O12A | 0.5693 (3) | −0.0032 (2) | 0.09562 (12) | 0.0584 (6) | 0.876 (2) |
H1A | 0.4880 | −0.0083 | 0.0657 | 0.088* | 0.876 (2) |
O21A | 0.8599 (3) | 0.0121 (2) | 0.33185 (10) | 0.0461 (5) | 0.876 (2) |
C1B | 0.7885 (3) | 0.3467 (2) | 0.12841 (14) | 0.0335 (6) | 0.876 (2) |
C2B | 0.7885 (3) | 0.3357 (2) | 0.04688 (14) | 0.0335 (6) | 0.876 (2) |
C3B | 0.6507 (3) | 0.3319 (3) | 0.00137 (16) | 0.0429 (7) | 0.876 (2) |
H3B | 0.6512 | 0.3246 | −0.0537 | 0.051* | 0.876 (2) |
C4B | 0.5132 (4) | 0.3388 (3) | 0.03635 (18) | 0.0509 (8) | 0.876 (2) |
H4B | 0.4188 | 0.3355 | 0.0051 | 0.061* | 0.876 (2) |
C5B | 0.5107 (4) | 0.3504 (3) | 0.11661 (19) | 0.0505 (8) | 0.876 (2) |
H5B | 0.4157 | 0.3555 | 0.1403 | 0.061* | 0.876 (2) |
C6B | 0.6481 (3) | 0.3544 (3) | 0.16136 (15) | 0.0417 (7) | 0.876 (2) |
H6B | 0.6467 | 0.3626 | 0.2163 | 0.050* | 0.876 (2) |
C11B | 0.9351 (3) | 0.3525 (2) | 0.17578 (13) | 0.0362 (6) | 0.876 (2) |
H11B | 1.0318 | 0.3591 | 0.1489 | 0.043* | 0.876 (2) |
C12B | 0.9469 (3) | 0.3493 (2) | 0.25290 (13) | 0.0408 (7) | 0.876 (2) |
H12B | 0.8521 | 0.3422 | 0.2814 | 0.049* | 0.876 (2) |
C13B | 1.1002 (4) | 0.3566 (2) | 0.29525 (14) | 0.0403 (6) | 0.876 (2) |
C21B | 0.9331 (3) | 0.3141 (3) | −0.06611 (13) | 0.0354 (6) | 0.876 (2) |
H21E | 0.9263 | 0.3928 | −0.0906 | 0.043* | 0.876 (2) |
H21F | 0.8372 | 0.2333 | −0.0871 | 0.043* | 0.876 (2) |
C22B | 1.0954 (4) | 0.3014 (3) | −0.08263 (15) | 0.0448 (7) | 0.876 (2) |
H22G | 1.1891 | 0.3847 | −0.0654 | 0.067* | 0.876 (2) |
H22H | 1.0987 | 0.2837 | −0.1386 | 0.067* | 0.876 (2) |
H22I | 1.1045 | 0.2275 | −0.0548 | 0.067* | 0.876 (2) |
O11B | 1.0898 (2) | 0.34100 (19) | 0.36854 (10) | 0.0481 (5) | 0.876 (2) |
H1B | 1.1827 | 0.3460 | 0.3880 | 0.072* | 0.876 (2) |
O12B | 1.2329 (3) | 0.3776 (2) | 0.26032 (11) | 0.0467 (5) | 0.876 (2) |
O21B | 0.9293 (2) | 0.32927 (19) | 0.01674 (10) | 0.0383 (5) | 0.876 (2) |
C1C | 0.2212 (3) | 0.6717 (2) | 0.42538 (12) | 0.0383 (5) | |
C2C | 0.2336 (3) | 0.6865 (2) | 0.34524 (12) | 0.0387 (5) | |
C3C | 0.1000 (3) | 0.6899 (2) | 0.29955 (14) | 0.0519 (6) | |
H3C | 0.1096 | 0.7004 | 0.2454 | 0.062* | |
C4C | −0.0476 (3) | 0.6779 (3) | 0.33352 (15) | 0.0573 (7) | |
H4C | −0.1396 | 0.6791 | 0.3022 | 0.069* | |
C5C | −0.0623 (3) | 0.6642 (2) | 0.41232 (15) | 0.0536 (7) | |
H5C | −0.1636 | 0.6567 | 0.4352 | 0.064* | |
C6C | 0.0706 (3) | 0.6614 (2) | 0.45758 (13) | 0.0467 (6) | |
H6C | 0.0600 | 0.6522 | 0.5118 | 0.056* | |
C11C | 0.3617 (3) | 0.66488 (19) | 0.47177 (12) | 0.0386 (5) | |
H11C | 0.4601 | 0.6754 | 0.4454 | 0.046* | |
C12C | 0.3664 (3) | 0.6453 (2) | 0.54770 (12) | 0.0444 (6) | |
H12C | 0.2711 | 0.6359 | 0.5762 | 0.053* | |
C13C | 0.5136 (3) | 0.6378 (2) | 0.58787 (12) | 0.0430 (6) | |
C21C | 0.3994 (3) | 0.7040 (2) | 0.23407 (11) | 0.0406 (6) | |
H21A | 0.3936 | 0.7882 | 0.2171 | 0.049* | |
H21B | 0.3084 | 0.6279 | 0.2057 | 0.049* | |
C22C | 0.5668 (3) | 0.6999 (2) | 0.21845 (12) | 0.0456 (6) | |
H22A | 0.6551 | 0.7730 | 0.2491 | 0.068* | |
H22B | 0.5862 | 0.7099 | 0.1631 | 0.068* | |
H22C | 0.5686 | 0.6142 | 0.2330 | 0.068* | |
O11C | 0.49716 (19) | 0.61046 (16) | 0.65985 (8) | 0.0557 (5) | |
H1C | 0.5869 | 0.6081 | 0.6787 | 0.084* | |
O12C | 0.6474 (2) | 0.65866 (16) | 0.55414 (8) | 0.0515 (4) | |
O21C | 0.38280 (17) | 0.69618 (15) | 0.31622 (8) | 0.0435 (4) | |
C1D | 1.0226 (10) | 0.0482 (7) | 0.2390 (4) | 0.0386 (17)* | 0.124 (2) |
C2D | 1.0064 (12) | 0.0102 (8) | 0.3149 (4) | 0.0386 (17)* | 0.124 (2) |
C3D | 1.1339 (14) | −0.0175 (10) | 0.3546 (5) | 0.0386 (17)* | 0.124 (2) |
H3D | 1.1208 | −0.0458 | 0.4062 | 0.046* | 0.124 (2) |
C4D | 1.2788 (14) | −0.0024 (12) | 0.3171 (6) | 0.0386 (17)* | 0.124 (2) |
H4D | 1.3662 | −0.0188 | 0.3439 | 0.046* | 0.124 (2) |
C5D | 1.2986 (13) | 0.0354 (12) | 0.2424 (6) | 0.0386 (17)* | 0.124 (2) |
H5D | 1.3976 | 0.0438 | 0.2170 | 0.046* | 0.124 (2) |
C6D | 1.1710 (11) | 0.0613 (9) | 0.2043 (5) | 0.0386 (17)* | 0.124 (2) |
H6D | 1.1853 | 0.0890 | 0.1526 | 0.046* | 0.124 (2) |
C11D | 0.8902 (8) | 0.0913 (5) | 0.2057 (4) | 0.0386 (17)* | 0.124 (2) |
H11D | 0.7763 | 0.0248 | 0.2159 | 0.046* | 0.124 (2) |
C12D | 0.8950 (8) | 0.1272 (6) | 0.1203 (3) | 0.0386 (17)* | 0.124 (2) |
H12D | 0.9967 | 0.1256 | 0.0952 | 0.046* | 0.124 (2) |
C13D | 0.7324 (10) | 0.0497 (7) | 0.0709 (4) | 0.0386 (17)* | 0.124 (2) |
C21D | 0.8448 (16) | −0.0161 (12) | 0.4273 (5) | 0.0386 (17)* | 0.124 (2) |
H21G | 0.9383 | 0.0568 | 0.4566 | 0.046* | 0.124 (2) |
H21H | 0.8496 | −0.1024 | 0.4404 | 0.046* | 0.124 (2) |
C22D | 0.6783 (16) | −0.0116 (15) | 0.4483 (5) | 0.0386 (17)* | 0.124 (2) |
H22J | 0.6655 | −0.0219 | 0.5041 | 0.058* | 0.124 (2) |
H22K | 0.5867 | −0.0843 | 0.4191 | 0.058* | 0.124 (2) |
H22L | 0.6750 | 0.0744 | 0.4352 | 0.058* | 0.124 (2) |
O11D | 0.7562 (13) | 0.0444 (9) | −0.0043 (4) | 0.0386 (17)* | 0.124 (2) |
H11E | 0.6641 | 0.0012 | −0.0289 | 0.058* | 0.124 (2) |
O12D | 0.5934 (9) | 0.0114 (8) | 0.0960 (5) | 0.0386 (17)* | 0.124 (2) |
O21D | 0.8584 (12) | −0.0007 (9) | 0.3461 (4) | 0.0386 (17)* | 0.124 (2) |
C1E | 0.7828 (11) | 0.3225 (7) | 0.1120 (5) | 0.0386 (17)* | 0.124 (2) |
C2E | 0.7926 (13) | 0.3444 (8) | 0.0336 (5) | 0.0386 (17)* | 0.124 (2) |
C3E | 0.6643 (15) | 0.3668 (11) | −0.0075 (6) | 0.0386 (17)* | 0.124 (2) |
H3E | 0.6712 | 0.3817 | −0.0613 | 0.046* | 0.124 (2) |
C4E | 0.5264 (15) | 0.3669 (13) | 0.0317 (7) | 0.0386 (17)* | 0.124 (2) |
H4E | 0.4388 | 0.3820 | 0.0041 | 0.046* | 0.124 (2) |
C5E | 0.5146 (14) | 0.3458 (13) | 0.1091 (7) | 0.0386 (17)* | 0.124 (2) |
H5E | 0.4203 | 0.3468 | 0.1353 | 0.046* | 0.124 (2) |
C6E | 0.6424 (12) | 0.3228 (10) | 0.1488 (5) | 0.0386 (17)* | 0.124 (2) |
H6E | 0.6338 | 0.3068 | 0.2025 | 0.046* | 0.124 (2) |
C11E | 0.9126 (9) | 0.2761 (6) | 0.1467 (4) | 0.0386 (17)* | 0.124 (2) |
H11F | 1.0277 | 0.3412 | 0.1370 | 0.046* | 0.124 (2) |
C12E | 0.9055 (9) | 0.2403 (6) | 0.2322 (4) | 0.0386 (17)* | 0.124 (2) |
H12E | 0.8023 | 0.2408 | 0.2562 | 0.046* | 0.124 (2) |
C13E | 1.0645 (11) | 0.3168 (7) | 0.2831 (4) | 0.0386 (17)* | 0.124 (2) |
C21E | 0.9380 (16) | 0.3355 (12) | −0.0822 (4) | 0.0386 (17)* | 0.124 (2) |
H21I | 0.9374 | 0.4185 | −0.1035 | 0.046* | 0.124 (2) |
H21J | 0.8374 | 0.2594 | −0.1042 | 0.046* | 0.124 (2) |
C22E | 1.0965 (16) | 0.3150 (15) | −0.1027 (5) | 0.0386 (17)* | 0.124 (2) |
H22M | 1.1011 | 0.3084 | −0.1593 | 0.058* | 0.124 (2) |
H22N | 1.0954 | 0.2325 | −0.0813 | 0.058* | 0.124 (2) |
H22O | 1.1950 | 0.3910 | −0.0806 | 0.058* | 0.124 (2) |
O11E | 1.0396 (14) | 0.3063 (9) | 0.3571 (4) | 0.0386 (17)* | 0.124 (2) |
H11G | 1.1299 | 0.3497 | 0.3830 | 0.058* | 0.124 (2) |
O12E | 1.2033 (10) | 0.3675 (7) | 0.2571 (5) | 0.0386 (17)* | 0.124 (2) |
O21E | 0.9371 (13) | 0.3445 (9) | 0.0012 (4) | 0.0386 (17)* | 0.124 (2) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0517 (17) | 0.0311 (14) | 0.0388 (16) | 0.0136 (13) | 0.0141 (13) | 0.0042 (11) |
C2A | 0.0439 (17) | 0.0392 (15) | 0.0404 (17) | 0.0132 (13) | 0.0096 (13) | 0.0004 (12) |
C3A | 0.0512 (19) | 0.0520 (19) | 0.0458 (17) | 0.0199 (16) | 0.0086 (14) | 0.0015 (14) |
C4A | 0.0473 (19) | 0.054 (2) | 0.068 (2) | 0.0208 (16) | 0.0072 (15) | 0.0002 (16) |
C5A | 0.053 (2) | 0.0555 (19) | 0.069 (2) | 0.0239 (16) | 0.0231 (16) | 0.0051 (16) |
C6A | 0.065 (2) | 0.0455 (17) | 0.0446 (18) | 0.0222 (15) | 0.0219 (15) | 0.0031 (13) |
C11A | 0.0577 (18) | 0.0315 (14) | 0.0387 (16) | 0.0146 (13) | 0.0153 (13) | 0.0028 (11) |
C12A | 0.0614 (19) | 0.0382 (15) | 0.0389 (16) | 0.0193 (14) | 0.0142 (13) | 0.0051 (12) |
C13A | 0.065 (2) | 0.0314 (15) | 0.0370 (17) | 0.0148 (14) | 0.0128 (14) | 0.0042 (12) |
C21A | 0.0558 (18) | 0.0586 (19) | 0.0285 (16) | 0.0268 (15) | 0.0062 (12) | 0.0016 (12) |
C22A | 0.0528 (18) | 0.069 (2) | 0.0363 (17) | 0.0246 (16) | 0.0078 (13) | 0.0028 (14) |
O11A | 0.0632 (14) | 0.0536 (13) | 0.0315 (11) | 0.0145 (11) | 0.0119 (9) | 0.0058 (8) |
O12A | 0.0741 (15) | 0.0621 (14) | 0.0405 (12) | 0.0258 (11) | 0.0200 (11) | 0.0091 (9) |
O21A | 0.0435 (11) | 0.0631 (12) | 0.0301 (11) | 0.0187 (9) | 0.0065 (8) | 0.0013 (8) |
C1B | 0.0376 (15) | 0.0333 (14) | 0.0308 (14) | 0.0146 (12) | 0.0040 (11) | 0.0036 (10) |
C2B | 0.0347 (15) | 0.0327 (14) | 0.0339 (15) | 0.0134 (11) | 0.0047 (11) | 0.0035 (10) |
C3B | 0.0403 (16) | 0.0552 (19) | 0.0349 (15) | 0.0209 (15) | −0.0031 (12) | 0.0022 (12) |
C4B | 0.0364 (17) | 0.067 (2) | 0.0522 (19) | 0.0226 (16) | 0.0010 (13) | 0.0041 (15) |
C5B | 0.0437 (17) | 0.0582 (18) | 0.0563 (19) | 0.0261 (14) | 0.0139 (14) | 0.0036 (14) |
C6B | 0.0456 (17) | 0.0462 (17) | 0.0349 (15) | 0.0188 (14) | 0.0090 (12) | 0.0033 (12) |
C11B | 0.0464 (16) | 0.0321 (14) | 0.0291 (14) | 0.0136 (12) | 0.0059 (11) | 0.0044 (10) |
C12B | 0.0489 (17) | 0.0446 (16) | 0.0298 (15) | 0.0188 (13) | 0.0041 (12) | 0.0022 (11) |
C13B | 0.0595 (19) | 0.0349 (15) | 0.0288 (14) | 0.0202 (14) | 0.0059 (13) | 0.0043 (11) |
C21B | 0.0369 (15) | 0.0435 (16) | 0.0246 (14) | 0.0140 (12) | 0.0024 (10) | 0.0017 (11) |
C22B | 0.0479 (17) | 0.0572 (18) | 0.0341 (16) | 0.0249 (14) | 0.0089 (13) | 0.0044 (13) |
O11B | 0.0549 (14) | 0.0664 (13) | 0.0278 (10) | 0.0282 (11) | 0.0041 (8) | 0.0055 (9) |
O12B | 0.0518 (13) | 0.0585 (12) | 0.0290 (10) | 0.0190 (10) | 0.0096 (9) | 0.0092 (8) |
O21B | 0.0377 (10) | 0.0567 (12) | 0.0246 (10) | 0.0226 (9) | 0.0037 (8) | 0.0023 (8) |
C1C | 0.0407 (14) | 0.0386 (13) | 0.0344 (13) | 0.0136 (11) | 0.0082 (10) | −0.0003 (10) |
C2C | 0.0339 (13) | 0.0437 (14) | 0.0367 (13) | 0.0131 (11) | 0.0045 (10) | −0.0010 (10) |
C3C | 0.0440 (15) | 0.0720 (17) | 0.0411 (14) | 0.0241 (13) | 0.0036 (11) | 0.0029 (12) |
C4C | 0.0409 (15) | 0.0758 (19) | 0.0599 (18) | 0.0278 (14) | 0.0044 (12) | 0.0022 (14) |
C5C | 0.0447 (16) | 0.0603 (17) | 0.0607 (17) | 0.0243 (13) | 0.0187 (13) | 0.0053 (13) |
C6C | 0.0515 (16) | 0.0478 (14) | 0.0418 (14) | 0.0189 (12) | 0.0153 (12) | 0.0049 (11) |
C11C | 0.0436 (14) | 0.0365 (13) | 0.0343 (13) | 0.0136 (11) | 0.0079 (10) | 0.0021 (9) |
C12C | 0.0514 (15) | 0.0490 (14) | 0.0334 (13) | 0.0189 (12) | 0.0123 (11) | 0.0060 (10) |
C13C | 0.0612 (17) | 0.0415 (13) | 0.0255 (12) | 0.0190 (12) | 0.0049 (11) | 0.0016 (10) |
C21C | 0.0405 (14) | 0.0543 (14) | 0.0280 (12) | 0.0190 (11) | 0.0028 (9) | 0.0048 (10) |
C22C | 0.0437 (14) | 0.0591 (15) | 0.0355 (13) | 0.0207 (12) | 0.0070 (10) | 0.0048 (11) |
O11C | 0.0534 (11) | 0.0795 (12) | 0.0327 (9) | 0.0229 (9) | 0.0045 (7) | 0.0121 (8) |
O12C | 0.0570 (11) | 0.0668 (11) | 0.0339 (9) | 0.0264 (9) | 0.0128 (8) | 0.0037 (7) |
O21C | 0.0369 (9) | 0.0689 (11) | 0.0267 (8) | 0.0227 (8) | 0.0026 (6) | 0.0021 (7) |
Geometric parameters (Å, º) top
C1A—C6A | 1.397 (4) | C12C—C13C | 1.458 (3) |
C1A—C2A | 1.401 (3) | C12C—H12C | 0.9500 |
C1A—C11A | 1.470 (4) | C13C—O12C | 1.260 (3) |
C2A—O21A | 1.368 (3) | C13C—O11C | 1.290 (2) |
C2A—C3A | 1.389 (4) | C21C—O21C | 1.433 (2) |
C3A—C4A | 1.379 (4) | C21C—C22C | 1.499 (3) |
C3A—H3A | 0.9500 | C21C—H21A | 0.9900 |
C4A—C5A | 1.383 (4) | C21C—H21B | 0.9900 |
C4A—H4A | 0.9500 | C22C—H22A | 0.9800 |
C5A—C6A | 1.366 (4) | C22C—H22B | 0.9800 |
C5A—H5A | 0.9500 | C22C—H22C | 0.9800 |
C6A—H6A | 0.9500 | O11C—H1C | 0.8400 |
C11A—C12A | 1.334 (3) | C1D—C2D | 1.3866 |
C11A—H11A | 0.9500 | C1D—C6D | 1.3961 |
C12A—C13A | 1.454 (4) | C1D—C11D | 1.4979 |
C12A—H12A | 0.9500 | C2D—O21D | 1.3716 |
C13A—O11A | 1.262 (3) | C2D—C3D | 1.4116 |
C13A—O12A | 1.285 (3) | C3D—C4D | 1.3884 |
C21A—O21A | 1.440 (3) | C3D—H3D | 0.9500 |
C21A—C22A | 1.497 (3) | C4D—C5D | 1.3674 |
C21A—H21C | 0.9900 | C4D—H4D | 0.9500 |
C21A—H21D | 0.9900 | C5D—C6D | 1.3890 |
C22A—H22D | 0.9800 | C5D—H5D | 0.9500 |
C22A—H22E | 0.9800 | C6D—H6D | 0.9500 |
C22A—H22F | 0.9800 | C11D—C12D | 1.5394 |
O12A—H1A | 0.8400 | C11D—C12E | 1.6166 |
C1B—C6B | 1.389 (3) | C11D—H11D | 1.0000 |
C1B—C2B | 1.407 (3) | C12D—C13D | 1.5337 |
C1B—C11B | 1.462 (3) | C12D—C11E | 1.6084 |
C2B—O21B | 1.366 (3) | C12D—H12D | 1.0000 |
C2B—C3B | 1.389 (3) | C13D—O12D | 1.2148 |
C3B—C4B | 1.379 (3) | C13D—O11D | 1.3234 |
C3B—H3B | 0.9500 | C21D—O21D | 1.4229 |
C4B—C5B | 1.387 (4) | C21D—C22D | 1.5151 |
C4B—H4B | 0.9500 | C21D—H21G | 0.9900 |
C5B—C6B | 1.378 (4) | C21D—H21H | 0.9900 |
C5B—H5B | 0.9500 | C22D—H22J | 0.9800 |
C6B—H6B | 0.9500 | C22D—H22K | 0.9800 |
C11B—C12B | 1.334 (3) | C22D—H22L | 0.9800 |
C11B—H11B | 0.9500 | O11D—H11E | 0.8400 |
C12B—C13B | 1.463 (3) | C1E—C2E | 1.3829 |
C12B—H12B | 0.9500 | C1E—C6E | 1.3919 |
C13B—O12B | 1.262 (3) | C1E—C11E | 1.5118 |
C13B—O11B | 1.285 (3) | C2E—O21E | 1.3878 |
C21B—O21B | 1.436 (3) | C2E—C3E | 1.3985 |
C21B—C22B | 1.497 (3) | C3E—C4E | 1.3933 |
C21B—H21E | 0.9900 | C3E—H3E | 0.9500 |
C21B—H21F | 0.9900 | C4E—C5E | 1.3664 |
C22B—H22G | 0.9800 | C4E—H4E | 0.9500 |
C22B—H22H | 0.9800 | C5E—C6E | 1.3865 |
C22B—H22I | 0.9800 | C5E—H5E | 0.9500 |
O11B—H1B | 0.8400 | C6E—H6E | 0.9500 |
C1C—C6C | 1.401 (3) | C11E—C12E | 1.5393 |
C1C—C2C | 1.403 (3) | C11E—H11F | 1.0000 |
C1C—C11C | 1.458 (3) | C12E—C13E | 1.5245 |
C2C—O21C | 1.369 (2) | C12E—H12E | 1.0000 |
C2C—C3C | 1.388 (3) | C13E—O12E | 1.2245 |
C3C—C4C | 1.387 (3) | C13E—O11E | 1.3047 |
C3C—H3C | 0.9500 | C21E—O21E | 1.4391 |
C4C—C5C | 1.380 (3) | C21E—C22E | 1.5213 |
C4C—H4C | 0.9500 | C21E—H21I | 0.9900 |
C5C—C6C | 1.377 (3) | C21E—H21J | 0.9900 |
C5C—H5C | 0.9500 | C22E—H22M | 0.9800 |
C6C—H6C | 0.9500 | C22E—H22N | 0.9800 |
C11C—C12C | 1.339 (3) | C22E—H22O | 0.9800 |
C11C—H11C | 0.9500 | O11E—H11G | 0.8400 |
| | | |
C6A—C1A—C2A | 118.0 (3) | O21C—C21C—C22C | 106.68 (16) |
C6A—C1A—C11A | 122.2 (2) | O21C—C21C—H21A | 110.4 |
C2A—C1A—C11A | 119.7 (2) | C22C—C21C—H21A | 110.4 |
O21A—C2A—C3A | 123.7 (2) | O21C—C21C—H21B | 110.4 |
O21A—C2A—C1A | 115.9 (2) | C22C—C21C—H21B | 110.4 |
C3A—C2A—C1A | 120.4 (3) | H21A—C21C—H21B | 108.6 |
C4A—C3A—C2A | 119.8 (3) | C21C—C22C—H22A | 109.5 |
C4A—C3A—H3A | 120.1 | C21C—C22C—H22B | 109.5 |
C2A—C3A—H3A | 120.1 | H22A—C22C—H22B | 109.5 |
C3A—C4A—C5A | 120.5 (3) | C21C—C22C—H22C | 109.5 |
C3A—C4A—H4A | 119.8 | H22A—C22C—H22C | 109.5 |
C5A—C4A—H4A | 119.8 | H22B—C22C—H22C | 109.5 |
C6A—C5A—C4A | 119.8 (3) | C13C—O11C—H1C | 109.5 |
C6A—C5A—H5A | 120.1 | C2C—O21C—C21C | 118.45 (15) |
C4A—C5A—H5A | 120.1 | C2D—C1D—C6D | 117.6 |
C5A—C6A—C1A | 121.5 (3) | C2D—C1D—C11D | 116.5 |
C5A—C6A—H6A | 119.2 | C6D—C1D—C11D | 125.3 |
C1A—C6A—H6A | 119.2 | O21D—C2D—C1D | 115.0 |
C12A—C11A—C1A | 127.2 (3) | O21D—C2D—C3D | 124.0 |
C12A—C11A—H11A | 116.4 | C1D—C2D—C3D | 121.0 |
C1A—C11A—H11A | 116.4 | C4D—C3D—C2D | 118.8 |
C11A—C12A—C13A | 122.7 (3) | C4D—C3D—H3D | 120.6 |
C11A—C12A—H12A | 118.6 | C2D—C3D—H3D | 120.6 |
C13A—C12A—H12A | 118.6 | C5D—C4D—C3D | 121.6 |
O11A—C13A—O12A | 123.2 (3) | C5D—C4D—H4D | 119.2 |
O11A—C13A—C12A | 118.7 (2) | C3D—C4D—H4D | 119.2 |
O12A—C13A—C12A | 118.1 (2) | C4D—C5D—C6D | 118.6 |
O21A—C21A—C22A | 107.1 (2) | C4D—C5D—H5D | 120.7 |
O21A—C21A—H21C | 110.3 | C6D—C5D—H5D | 120.7 |
C22A—C21A—H21C | 110.3 | C5D—C6D—C1D | 122.5 |
O21A—C21A—H21D | 110.3 | C5D—C6D—H6D | 118.7 |
C22A—C21A—H21D | 110.3 | C1D—C6D—H6D | 118.7 |
H21C—C21A—H21D | 108.6 | C1D—C11D—C12D | 119.2 |
C21A—C22A—H22D | 109.5 | C1D—C11D—C12E | 116.5 |
C21A—C22A—H22E | 109.5 | C12D—C11D—C12E | 89.6 |
H22D—C22A—H22E | 109.5 | C1D—C11D—H11D | 110.0 |
C21A—C22A—H22F | 109.5 | C12D—C11D—H11D | 110.0 |
H22D—C22A—H22F | 109.5 | C12E—C11D—H11D | 110.0 |
H22E—C22A—H22F | 109.5 | C13D—C12D—C11D | 114.6 |
C13A—O12A—H1A | 109.5 | C13D—C12D—C11E | 112.4 |
C2A—O21A—C21A | 118.73 (19) | C11D—C12D—C11E | 90.4 |
C6B—C1B—C2B | 118.1 (2) | C13D—C12D—H12D | 112.6 |
C6B—C1B—C11B | 122.0 (2) | C11D—C12D—H12D | 112.6 |
C2B—C1B—C11B | 119.9 (2) | C11E—C12D—H12D | 112.6 |
O21B—C2B—C3B | 123.3 (2) | O12D—C13D—O11D | 122.4 |
O21B—C2B—C1B | 116.3 (2) | O12D—C13D—C12D | 124.0 |
C3B—C2B—C1B | 120.4 (2) | O11D—C13D—C12D | 113.0 |
C4B—C3B—C2B | 119.7 (2) | O21D—C21D—C22D | 107.7 |
C4B—C3B—H3B | 120.1 | O21D—C21D—H21G | 110.2 |
C2B—C3B—H3B | 120.1 | C22D—C21D—H21G | 110.2 |
C3B—C4B—C5B | 120.9 (2) | O21D—C21D—H21H | 110.2 |
C3B—C4B—H4B | 119.5 | C22D—C21D—H21H | 110.2 |
C5B—C4B—H4B | 119.5 | H21G—C21D—H21H | 108.5 |
C6B—C5B—C4B | 119.0 (2) | C21D—C22D—H22J | 109.5 |
C6B—C5B—H5B | 120.5 | C21D—C22D—H22K | 109.5 |
C4B—C5B—H5B | 120.5 | H22J—C22D—H22K | 109.5 |
C5B—C6B—C1B | 121.9 (2) | C21D—C22D—H22L | 109.5 |
C5B—C6B—H6B | 119.1 | H22J—C22D—H22L | 109.5 |
C1B—C6B—H6B | 119.1 | H22K—C22D—H22L | 109.5 |
C12B—C11B—C1B | 126.5 (2) | C13D—O11D—H11E | 109.5 |
C12B—C11B—H11B | 116.7 | C2D—O21D—C21D | 118.0 |
C1B—C11B—H11B | 116.7 | C2E—C1E—C6E | 118.5 |
C11B—C12B—C13B | 122.5 (2) | C2E—C1E—C11E | 115.6 |
C11B—C12B—H12B | 118.8 | C6E—C1E—C11E | 124.9 |
C13B—C12B—H12B | 118.8 | C1E—C2E—O21E | 115.2 |
O12B—C13B—O11B | 123.4 (2) | C1E—C2E—C3E | 120.7 |
O12B—C13B—C12B | 120.6 (2) | O21E—C2E—C3E | 124.1 |
O11B—C13B—C12B | 115.9 (2) | C4E—C3E—C2E | 119.0 |
O21B—C21B—C22B | 107.09 (18) | C4E—C3E—H3E | 120.5 |
O21B—C21B—H21E | 110.3 | C2E—C3E—H3E | 120.5 |
C22B—C21B—H21E | 110.3 | C5E—C4E—C3E | 121.3 |
O21B—C21B—H21F | 110.3 | C5E—C4E—H4E | 119.4 |
C22B—C21B—H21F | 110.3 | C3E—C4E—H4E | 119.4 |
H21E—C21B—H21F | 108.6 | C4E—C5E—C6E | 119.0 |
C21B—C22B—H22G | 109.5 | C4E—C5E—H5E | 120.5 |
C21B—C22B—H22H | 109.5 | C6E—C5E—H5E | 120.5 |
H22G—C22B—H22H | 109.5 | C5E—C6E—C1E | 121.6 |
C21B—C22B—H22I | 109.5 | C5E—C6E—H6E | 119.2 |
H22G—C22B—H22I | 109.5 | C1E—C6E—H6E | 119.2 |
H22H—C22B—H22I | 109.5 | C1E—C11E—C12E | 119.6 |
C13B—O11B—H1B | 109.5 | C1E—C11E—C12D | 116.7 |
C2B—O21B—C21B | 118.34 (17) | C12E—C11E—C12D | 89.9 |
C6C—C1C—C2C | 117.9 (2) | C1E—C11E—H11F | 109.7 |
C6C—C1C—C11C | 122.4 (2) | C12E—C11E—H11F | 109.7 |
C2C—C1C—C11C | 119.69 (19) | C12D—C11E—H11F | 109.7 |
O21C—C2C—C3C | 123.3 (2) | C13E—C12E—C11E | 115.4 |
O21C—C2C—C1C | 115.99 (18) | C13E—C12E—C11D | 112.1 |
C3C—C2C—C1C | 120.8 (2) | C11E—C12E—C11D | 90.1 |
C2C—C3C—C4C | 119.6 (2) | C13E—C12E—H12E | 112.5 |
C2C—C3C—H3C | 120.2 | C11E—C12E—H12E | 112.5 |
C4C—C3C—H3C | 120.2 | C11D—C12E—H12E | 112.5 |
C5C—C4C—C3C | 120.7 (2) | O12E—C13E—O11E | 123.8 |
C5C—C4C—H4C | 119.6 | O12E—C13E—C12E | 123.0 |
C3C—C4C—H4C | 119.6 | O11E—C13E—C12E | 112.5 |
C6C—C5C—C4C | 119.6 (2) | O21E—C21E—C22E | 107.3 |
C6C—C5C—H5C | 120.2 | O21E—C21E—H21I | 110.3 |
C4C—C5C—H5C | 120.2 | C22E—C21E—H21I | 110.3 |
C5C—C6C—C1C | 121.4 (2) | O21E—C21E—H21J | 110.3 |
C5C—C6C—H6C | 119.3 | C22E—C21E—H21J | 110.3 |
C1C—C6C—H6C | 119.3 | H21I—C21E—H21J | 108.5 |
C12C—C11C—C1C | 126.7 (2) | C21E—C22E—H22M | 109.5 |
C12C—C11C—H11C | 116.6 | C21E—C22E—H22N | 109.5 |
C1C—C11C—H11C | 116.6 | H22M—C22E—H22N | 109.5 |
C11C—C12C—C13C | 121.9 (2) | C21E—C22E—H22O | 109.5 |
C11C—C12C—H12C | 119.0 | H22M—C22E—H22O | 109.5 |
C13C—C12C—H12C | 119.0 | H22N—C22E—H22O | 109.5 |
O12C—C13C—O11C | 123.0 (2) | C13E—O11E—H11G | 109.5 |
O12C—C13C—C12C | 121.7 (2) | C2E—O21E—C21E | 117.6 |
O11C—C13C—C12C | 115.3 (2) | | |
| | | |
C6A—C1A—C2A—O21A | −179.7 (2) | C6D—C1D—C2D—C3D | −1.6 |
C11A—C1A—C2A—O21A | −1.0 (3) | C11D—C1D—C2D—C3D | −172.7 |
C6A—C1A—C2A—C3A | 1.7 (4) | O21D—C2D—C3D—C4D | −179.8 |
C11A—C1A—C2A—C3A | −179.5 (2) | C1D—C2D—C3D—C4D | 1.7 |
O21A—C2A—C3A—C4A | −179.7 (2) | C2D—C3D—C4D—C5D | −1.5 |
C1A—C2A—C3A—C4A | −1.3 (4) | C3D—C4D—C5D—C6D | 1.1 |
C2A—C3A—C4A—C5A | 0.6 (4) | C4D—C5D—C6D—C1D | −1.0 |
C3A—C4A—C5A—C6A | −0.4 (4) | C2D—C1D—C6D—C5D | 1.3 |
C4A—C5A—C6A—C1A | 0.8 (4) | C11D—C1D—C6D—C5D | 171.5 |
C2A—C1A—C6A—C5A | −1.5 (4) | C2D—C1D—C11D—C12D | −176.6 |
C11A—C1A—C6A—C5A | 179.8 (2) | C6D—C1D—C11D—C12D | 13.1 |
C6A—C1A—C11A—C12A | 1.0 (4) | C2D—C1D—C11D—C12E | 77.8 |
C2A—C1A—C11A—C12A | −177.8 (2) | C6D—C1D—C11D—C12E | −92.6 |
C1A—C11A—C12A—C13A | 179.3 (2) | C1D—C11D—C12D—C13D | 125.2 |
C11A—C12A—C13A—O11A | 179.4 (2) | C12E—C11D—C12D—C13D | −114.3 |
C11A—C12A—C13A—O12A | −1.2 (4) | C1D—C11D—C12D—C11E | −119.8 |
C3A—C2A—O21A—C21A | 0.1 (4) | C12E—C11D—C12D—C11E | 0.7 |
C1A—C2A—O21A—C21A | −178.4 (2) | C11D—C12D—C13D—O12D | 31.8 |
C22A—C21A—O21A—C2A | 175.7 (2) | C11E—C12D—C13D—O12D | −69.5 |
C6B—C1B—C2B—O21B | 179.6 (2) | C11D—C12D—C13D—O11D | −157.0 |
C11B—C1B—C2B—O21B | 0.8 (3) | C11E—C12D—C13D—O11D | 101.6 |
C6B—C1B—C2B—C3B | −0.4 (3) | C1D—C2D—O21D—C21D | −169.1 |
C11B—C1B—C2B—C3B | −179.2 (2) | C3D—C2D—O21D—C21D | 12.3 |
O21B—C2B—C3B—C4B | 179.9 (2) | C22D—C21D—O21D—C2D | 174.3 |
C1B—C2B—C3B—C4B | −0.1 (4) | C6E—C1E—C2E—O21E | 179.2 |
C2B—C3B—C4B—C5B | 0.5 (4) | C11E—C1E—C2E—O21E | −11.3 |
C3B—C4B—C5B—C6B | −0.3 (4) | C6E—C1E—C2E—C3E | 0.2 |
C4B—C5B—C6B—C1B | −0.2 (4) | C11E—C1E—C2E—C3E | 169.8 |
C2B—C1B—C6B—C5B | 0.6 (4) | C1E—C2E—C3E—C4E | 0.1 |
C11B—C1B—C6B—C5B | 179.3 (2) | O21E—C2E—C3E—C4E | −178.7 |
C6B—C1B—C11B—C12B | 8.5 (4) | C2E—C3E—C4E—C5E | 0.0 |
C2B—C1B—C11B—C12B | −172.8 (2) | C3E—C4E—C5E—C6E | −0.5 |
C1B—C11B—C12B—C13B | −179.6 (2) | C4E—C5E—C6E—C1E | 0.9 |
C11B—C12B—C13B—O12B | 6.0 (4) | C2E—C1E—C6E—C5E | −0.7 |
C11B—C12B—C13B—O11B | −174.2 (2) | C11E—C1E—C6E—C5E | −169.2 |
C3B—C2B—O21B—C21B | −1.8 (3) | C2E—C1E—C11E—C12E | −176.1 |
C1B—C2B—O21B—C21B | 178.21 (19) | C6E—C1E—C11E—C12E | −7.4 |
C22B—C21B—O21B—C2B | −176.56 (19) | C2E—C1E—C11E—C12D | −69.7 |
C6C—C1C—C2C—O21C | −179.96 (19) | C6E—C1E—C11E—C12D | 99.1 |
C11C—C1C—C2C—O21C | −1.2 (3) | C13D—C12D—C11E—C1E | −7.3 |
C6C—C1C—C2C—C3C | −0.4 (3) | C11D—C12D—C11E—C1E | −124.2 |
C11C—C1C—C2C—C3C | 178.4 (2) | C13D—C12D—C11E—C12E | 116.2 |
O21C—C2C—C3C—C4C | 179.3 (2) | C11D—C12D—C11E—C12E | −0.7 |
C1C—C2C—C3C—C4C | −0.3 (3) | C1E—C11E—C12E—C13E | −123.6 |
C2C—C3C—C4C—C5C | 0.7 (4) | C12D—C11E—C12E—C13E | 115.4 |
C3C—C4C—C5C—C6C | −0.5 (4) | C1E—C11E—C12E—C11D | 121.7 |
C4C—C5C—C6C—C1C | −0.2 (4) | C12D—C11E—C12E—C11D | 0.7 |
C2C—C1C—C6C—C5C | 0.6 (3) | C1D—C11D—C12E—C13E | 4.5 |
C11C—C1C—C6C—C5C | −178.1 (2) | C12D—C11D—C12E—C13E | −118.3 |
C6C—C1C—C11C—C12C | 1.7 (3) | C1D—C11D—C12E—C11E | 122.1 |
C2C—C1C—C11C—C12C | −176.9 (2) | C12D—C11D—C12E—C11E | −0.7 |
C1C—C11C—C12C—C13C | 178.88 (19) | C11E—C12E—C13E—O12E | −23.8 |
C11C—C12C—C13C—O12C | 4.9 (3) | C11D—C12E—C13E—O12E | 77.5 |
C11C—C12C—C13C—O11C | −175.92 (19) | C11E—C12E—C13E—O11E | 165.0 |
C3C—C2C—O21C—C21C | −3.0 (3) | C11D—C12E—C13E—O11E | −93.7 |
C1C—C2C—O21C—C21C | 176.63 (17) | C1E—C2E—O21E—C21E | 165.9 |
C22C—C21C—O21C—C2C | −174.50 (18) | C3E—C2E—O21E—C21E | −15.2 |
C6D—C1D—C2D—O21D | 179.8 | C22E—C21E—O21E—C2E | −171.1 |
C11D—C1D—C2D—O21D | 8.7 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O12A—H1A···O11Ai | 0.84 | 1.73 | 2.566 (3) | 170 |
O11B—H1B···O12Cii | 0.84 | 1.76 | 2.591 (2) | 168 |
O11C—H1C···O12Bii | 0.84 | 1.80 | 2.622 (3) | 166 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z+1. |
(d12hlt_s) (
E)-3-(2-Ethoxyphenyl)propenoic acid and
trans-2,4-bis(2-ethoxyphenyl)-
trans-1,3-cyclobutane-dicarboxylic acid
top
Crystal data top
0.219(C22H24O6)·2.562(C11H12O3) | Z = 2 |
Mr = 576.62 | F(000) = 612 |
Triclinic, P1 | Dx = 1.285 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 8.6164 (10) Å | Cell parameters from 923 reflections |
b = 10.8765 (14) Å | θ = 2.4–24.1° |
c = 17.292 (2) Å | µ = 0.09 mm−1 |
α = 93.157 (2)° | T = 173 K |
β = 92.001 (2)° | Irregular, white |
γ = 112.657 (3)° | 0.45 × 0.24 × 0.14 mm |
V = 1490.4 (3) Å3 | |
Data collection top
CCD area detector diffractometer | 2989 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 25.5°, θmin = 1.2° |
phi and ω scans | h = −10→10 |
8551 measured reflections | k = −13→8 |
5499 independent reflections | l = −20→18 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.062P)2 + 0.0626P] where P = (Fo2 + 2Fc2)/3 |
5499 reflections | (Δ/σ)max = 0.001 |
418 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Crystal data top
0.219(C22H24O6)·2.562(C11H12O3) | γ = 112.657 (3)° |
Mr = 576.62 | V = 1490.4 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.6164 (10) Å | Mo Kα radiation |
b = 10.8765 (14) Å | µ = 0.09 mm−1 |
c = 17.292 (2) Å | T = 173 K |
α = 93.157 (2)° | 0.45 × 0.24 × 0.14 mm |
β = 92.001 (2)° | |
Data collection top
CCD area detector diffractometer | 2989 reflections with I > 2σ(I) |
8551 measured reflections | Rint = 0.023 |
5499 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.142 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.16 e Å−3 |
5499 reflections | Δρmin = −0.22 e Å−3 |
418 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 | Occ. (<1) |
C1A | 1.0120 (5) | 0.0257 (4) | 0.2201 (3) | 0.0485 (14) | 0.781 (3) |
C2A | 1.0060 (5) | 0.0216 (4) | 0.3008 (3) | 0.0487 (19) | 0.781 (3) |
C3A | 1.1473 (5) | 0.0300 (5) | 0.3463 (2) | 0.0545 (10) | 0.781 (3) |
H3A | 1.1429 | 0.0286 | 0.4010 | 0.065* | 0.781 (3) |
C4A | 1.2926 (5) | 0.0402 (6) | 0.3120 (2) | 0.0603 (12) | 0.781 (3) |
H4A | 1.3877 | 0.0434 | 0.3428 | 0.072* | 0.781 (3) |
C5A | 1.3004 (5) | 0.0457 (5) | 0.2317 (3) | 0.061 (3) | 0.781 (3) |
H5A | 1.4015 | 0.0547 | 0.2078 | 0.073* | 0.781 (3) |
C6A | 1.1619 (5) | 0.0381 (5) | 0.1877 (3) | 0.0549 (18) | 0.781 (3) |
H6A | 1.1684 | 0.0415 | 0.1330 | 0.066* | 0.781 (3) |
C11A | 0.8621 (4) | 0.0171 (3) | 0.17306 (17) | 0.0459 (8) | 0.781 (3) |
H11A | 0.7661 | 0.0112 | 0.2005 | 0.055* | 0.781 (3) |
C12A | 0.8464 (4) | 0.0167 (3) | 0.09625 (17) | 0.0525 (9) | 0.781 (3) |
H12A | 0.9403 | 0.0234 | 0.0670 | 0.063* | 0.781 (3) |
C13A | 0.6903 (5) | 0.0065 (4) | 0.0553 (2) | 0.0505 (9) | 0.781 (3) |
C21A | 0.8434 (4) | 0.0065 (5) | 0.4142 (2) | 0.0492 (14) | 0.781 (3) |
H21A | 0.9326 | 0.0863 | 0.4413 | 0.059* | 0.781 (3) |
H21B | 0.8551 | −0.0743 | 0.4325 | 0.059* | 0.781 (3) |
C22A | 0.6728 (5) | 0.0050 (4) | 0.4295 (3) | 0.0532 (13) | 0.781 (3) |
H22A | 0.6639 | 0.0863 | 0.4120 | 0.080* | 0.781 (3) |
H22B | 0.6566 | 0.0011 | 0.4853 | 0.080* | 0.781 (3) |
H22C | 0.5861 | −0.0735 | 0.4014 | 0.080* | 0.781 (3) |
O11A | 0.6944 (5) | 0.0094 (3) | −0.01777 (15) | 0.0577 (7) | 0.781 (3) |
H1A | 0.6001 | 0.0025 | −0.0368 | 0.087* | 0.781 (3) |
O12A | 0.5639 (5) | −0.0046 (4) | 0.09329 (16) | 0.0634 (17) | 0.781 (3) |
O21A | 0.8568 (3) | 0.0095 (3) | 0.3309 (2) | 0.0523 (13) | 0.781 (3) |
C1B | 0.7815 (4) | 0.3434 (5) | 0.1263 (3) | 0.0394 (15) | 0.781 (3) |
C2B | 0.7819 (4) | 0.3338 (4) | 0.0445 (3) | 0.038 (2) | 0.781 (3) |
C3B | 0.6445 (4) | 0.3311 (6) | −0.00049 (18) | 0.0452 (12) | 0.781 (3) |
H3B | 0.6449 | 0.3238 | −0.0555 | 0.054* | 0.781 (3) |
C4B | 0.5077 (5) | 0.3391 (6) | 0.03439 (19) | 0.0498 (16) | 0.781 (3) |
H4B | 0.4142 | 0.3382 | 0.0033 | 0.060* | 0.781 (3) |
C5B | 0.5044 (7) | 0.3483 (4) | 0.1145 (2) | 0.054 (6) | 0.781 (3) |
H5B | 0.4086 | 0.3522 | 0.1383 | 0.064* | 0.781 (3) |
C6B | 0.6407 (4) | 0.3516 (6) | 0.1592 (2) | 0.0461 (15) | 0.781 (3) |
H6B | 0.6388 | 0.3597 | 0.2141 | 0.055* | 0.781 (3) |
C11B | 0.9283 (3) | 0.3489 (3) | 0.17385 (15) | 0.0379 (7) | 0.781 (3) |
H11B | 1.0254 | 0.3553 | 0.1472 | 0.045* | 0.781 (3) |
C12B | 0.9393 (4) | 0.3458 (3) | 0.25109 (15) | 0.0427 (8) | 0.781 (3) |
H12B | 0.8441 | 0.3381 | 0.2796 | 0.051* | 0.781 (3) |
C13B | 1.0935 (5) | 0.3538 (5) | 0.2928 (2) | 0.0446 (11) | 0.781 (3) |
C21B | 0.9269 (4) | 0.3128 (5) | −0.0685 (2) | 0.0385 (13) | 0.781 (3) |
H21C | 0.9216 | 0.3923 | −0.0919 | 0.046* | 0.781 (3) |
H21D | 0.8298 | 0.2328 | −0.0903 | 0.046* | 0.781 (3) |
C22B | 1.0888 (4) | 0.2989 (5) | −0.0853 (3) | 0.0505 (14) | 0.781 (3) |
H22D | 1.1838 | 0.3805 | −0.0656 | 0.076* | 0.781 (3) |
H22E | 1.0938 | 0.2847 | −0.1414 | 0.076* | 0.781 (3) |
H22F | 1.0948 | 0.2225 | −0.0598 | 0.076* | 0.781 (3) |
O11B | 1.0788 (5) | 0.3355 (4) | 0.36527 (13) | 0.0470 (9) | 0.781 (3) |
H1B | 1.1712 | 0.3404 | 0.3856 | 0.071* | 0.781 (3) |
O12B | 1.2268 (5) | 0.3746 (3) | 0.25858 (16) | 0.0560 (16) | 0.781 (3) |
O21B | 0.9229 (3) | 0.3270 (3) | 0.01446 (18) | 0.0421 (11) | 0.781 (3) |
C1C | 0.2262 (3) | 0.6688 (2) | 0.42763 (12) | 0.0392 (5) | |
C2C | 0.2372 (3) | 0.6803 (2) | 0.34742 (12) | 0.0412 (6) | |
C3C | 0.1009 (3) | 0.6809 (3) | 0.30212 (14) | 0.0569 (7) | |
H3C | 0.1087 | 0.6888 | 0.2478 | 0.068* | |
C4C | −0.0454 (3) | 0.6700 (3) | 0.33638 (15) | 0.0628 (8) | |
H4C | −0.1386 | 0.6695 | 0.3051 | 0.075* | |
C5C | −0.0589 (3) | 0.6598 (3) | 0.41498 (15) | 0.0588 (7) | |
H5C | −0.1600 | 0.6533 | 0.4380 | 0.071* | |
C6C | 0.0753 (3) | 0.6591 (2) | 0.45989 (13) | 0.0492 (6) | |
H6C | 0.0657 | 0.6518 | 0.5142 | 0.059* | |
C11C | 0.3684 (3) | 0.6644 (2) | 0.47435 (12) | 0.0399 (6) | |
H11C | 0.4673 | 0.6750 | 0.4481 | 0.048* | |
C12C | 0.3736 (3) | 0.6471 (2) | 0.54975 (12) | 0.0463 (6) | |
H12C | 0.2779 | 0.6384 | 0.5781 | 0.056* | |
C13C | 0.5223 (3) | 0.6409 (2) | 0.59071 (12) | 0.0447 (6) | |
C21C | 0.4027 (3) | 0.6984 (2) | 0.23604 (11) | 0.0422 (6) | |
H21E | 0.3945 | 0.7817 | 0.2198 | 0.051* | |
H21F | 0.3124 | 0.6214 | 0.2073 | 0.051* | |
C22C | 0.5723 (3) | 0.6975 (2) | 0.21985 (12) | 0.0462 (6) | |
H22G | 0.6599 | 0.7704 | 0.2515 | 0.069* | |
H22H | 0.5919 | 0.7095 | 0.1648 | 0.069* | |
H22I | 0.5758 | 0.6119 | 0.2327 | 0.069* | |
O11C | 0.50424 (19) | 0.61456 (17) | 0.66263 (8) | 0.0582 (5) | |
H1C | 0.5944 | 0.6138 | 0.6822 | 0.087* | |
O12C | 0.6561 (2) | 0.66056 (16) | 0.55754 (8) | 0.0538 (5) | |
O21C | 0.38640 (17) | 0.69009 (16) | 0.31813 (8) | 0.0452 (4) | |
C1D | 1.0212 (6) | 0.0474 (5) | 0.2369 (3) | 0.032 (6)* | 0.219 (3) |
C2D | 1.0063 (8) | 0.0097 (6) | 0.3125 (3) | 0.030 (6)* | 0.219 (3) |
C3D | 1.1344 (10) | −0.0185 (7) | 0.3512 (4) | 0.044 (5)* | 0.219 (3) |
H3D | 1.1221 | −0.0467 | 0.4025 | 0.053* | 0.219 (3) |
C4D | 1.2787 (10) | −0.0043 (9) | 0.3130 (5) | 0.066 (8)* | 0.219 (3) |
H4D | 1.3665 | −0.0211 | 0.3391 | 0.079* | 0.219 (3) |
C5D | 1.2973 (9) | 0.0332 (9) | 0.2386 (4) | 0.050 (10)* | 0.219 (3) |
H5D | 1.3959 | 0.0410 | 0.2128 | 0.061* | 0.219 (3) |
C6D | 1.1691 (7) | 0.0597 (7) | 0.2015 (3) | 0.058 (9)* | 0.219 (3) |
H6D | 1.1826 | 0.0872 | 0.1501 | 0.069* | 0.219 (3) |
C11D | 0.8885 (5) | 0.0911 (4) | 0.2049 (2) | 0.034 (3)* | 0.219 (3) |
H11D | 0.7742 | 0.0251 | 0.2152 | 0.040* | 0.219 (3) |
C12D | 0.8918 (5) | 0.1267 (4) | 0.1198 (2) | 0.033 (2)* | 0.219 (3) |
H12D | 0.9931 | 0.1246 | 0.0942 | 0.039* | 0.219 (3) |
C13D | 0.7274 (6) | 0.0497 (5) | 0.0708 (3) | 0.033 (4)* | 0.219 (3) |
C21D | 0.8467 (11) | −0.0154 (9) | 0.4255 (3) | 0.063 (8)* | 0.219 (3) |
H21G | 0.9416 | 0.0573 | 0.4548 | 0.076* | 0.219 (3) |
H21H | 0.8509 | −0.1019 | 0.4378 | 0.076* | 0.219 (3) |
C22D | 0.6806 (12) | −0.0100 (11) | 0.4475 (3) | 0.048 (6)* | 0.219 (3) |
H22J | 0.6689 | −0.0201 | 0.5032 | 0.073* | 0.219 (3) |
H22K | 0.5876 | −0.0825 | 0.4183 | 0.073* | 0.219 (3) |
H22L | 0.6779 | 0.0761 | 0.4353 | 0.073* | 0.219 (3) |
O11D | 0.7495 (9) | 0.0441 (6) | −0.0045 (2) | 0.056 (4)* | 0.219 (3) |
H1D | 0.6564 | 0.0011 | −0.0288 | 0.085* | 0.219 (3) |
O12D | 0.5885 (6) | 0.0121 (6) | 0.0963 (3) | 0.048 (6)* | 0.219 (3) |
O21D | 0.8587 (8) | −0.0004 (6) | 0.3444 (3) | 0.037 (5)* | 0.219 (3) |
C1E | 0.7815 (7) | 0.3231 (5) | 0.1140 (3) | 0.039 (7)* | 0.219 (3) |
C2E | 0.7898 (9) | 0.3447 (6) | 0.0359 (3) | 0.029 (8)* | 0.219 (3) |
C3E | 0.6609 (10) | 0.3676 (8) | −0.0042 (4) | 0.056 (8)* | 0.219 (3) |
H3E | 0.6668 | 0.3822 | −0.0579 | 0.068* | 0.219 (3) |
C4E | 0.5237 (11) | 0.3686 (10) | 0.0357 (5) | 0.082 (11)* | 0.219 (3) |
H4E | 0.4357 | 0.3840 | 0.0088 | 0.098* | 0.219 (3) |
C5E | 0.5134 (10) | 0.3477 (10) | 0.1129 (5) | 0.05 (2)* | 0.219 (3) |
H5E | 0.4196 | 0.3493 | 0.1397 | 0.058* | 0.219 (3) |
C6E | 0.6418 (8) | 0.3241 (7) | 0.1516 (4) | 0.046 (8)* | 0.219 (3) |
H6E | 0.6342 | 0.3083 | 0.2051 | 0.055* | 0.219 (3) |
C11E | 0.9116 (5) | 0.2760 (4) | 0.1475 (2) | 0.027 (2)* | 0.219 (3) |
H11F | 1.0272 | 0.3406 | 0.1377 | 0.032* | 0.219 (3) |
C12E | 0.9060 (6) | 0.2405 (4) | 0.2326 (2) | 0.032 (2)* | 0.219 (3) |
H12E | 0.8032 | 0.2416 | 0.2572 | 0.038* | 0.219 (3) |
C13E | 1.0669 (7) | 0.3165 (5) | 0.2832 (3) | 0.030 (5)* | 0.219 (3) |
C21E | 0.9327 (11) | 0.3345 (9) | −0.0807 (3) | 0.046 (7)* | 0.219 (3) |
H21I | 0.9326 | 0.4176 | −0.1013 | 0.055* | 0.219 (3) |
H21J | 0.8309 | 0.2587 | −0.1028 | 0.055* | 0.219 (3) |
C22E | 1.0906 (11) | 0.3132 (10) | −0.1023 (3) | 0.042 (6)* | 0.219 (3) |
H22M | 1.0940 | 0.3063 | −0.1589 | 0.064* | 0.219 (3) |
H22N | 1.0892 | 0.2306 | −0.0817 | 0.064* | 0.219 (3) |
H22O | 1.1905 | 0.3888 | −0.0802 | 0.064* | 0.219 (3) |
O11E | 1.0434 (9) | 0.3064 (6) | 0.3571 (2) | 0.080 (7)* | 0.219 (3) |
H1E | 1.1347 | 0.3496 | 0.3828 | 0.120* | 0.219 (3) |
O12E | 1.2057 (7) | 0.3665 (5) | 0.2568 (3) | 0.021 (4)* | 0.219 (3) |
O21E | 0.9338 (9) | 0.3439 (6) | 0.0027 (3) | 0.037 (5)* | 0.219 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.062 (3) | 0.037 (2) | 0.047 (2) | 0.0166 (17) | 0.0209 (17) | 0.0076 (19) |
C2A | 0.055 (3) | 0.043 (3) | 0.046 (2) | 0.0163 (19) | 0.0128 (17) | 0.0005 (17) |
C3A | 0.057 (3) | 0.057 (3) | 0.049 (2) | 0.022 (2) | 0.0053 (17) | −0.0001 (18) |
C4A | 0.051 (3) | 0.065 (3) | 0.068 (3) | 0.026 (2) | 0.0099 (17) | −0.0010 (19) |
C5A | 0.054 (4) | 0.061 (4) | 0.073 (4) | 0.026 (2) | 0.032 (3) | 0.004 (2) |
C6A | 0.067 (3) | 0.051 (2) | 0.049 (2) | 0.0234 (19) | 0.0219 (18) | 0.006 (2) |
C11A | 0.064 (2) | 0.0350 (18) | 0.0390 (19) | 0.0179 (16) | 0.0141 (15) | 0.0039 (14) |
C12A | 0.073 (2) | 0.043 (2) | 0.0396 (19) | 0.0179 (18) | 0.0213 (16) | 0.0057 (15) |
C13A | 0.079 (3) | 0.038 (2) | 0.035 (2) | 0.021 (2) | 0.0134 (19) | 0.0037 (19) |
C21A | 0.055 (3) | 0.065 (3) | 0.027 (2) | 0.023 (2) | 0.0071 (14) | −0.0005 (17) |
C22A | 0.052 (3) | 0.074 (3) | 0.0344 (19) | 0.025 (2) | 0.0119 (16) | 0.0048 (19) |
O11A | 0.0656 (18) | 0.0661 (17) | 0.0375 (14) | 0.0193 (17) | 0.0139 (13) | 0.0116 (13) |
O12A | 0.084 (2) | 0.056 (2) | 0.048 (2) | 0.0220 (14) | 0.0362 (14) | 0.0090 (11) |
O21A | 0.052 (2) | 0.073 (2) | 0.0307 (13) | 0.0221 (14) | 0.0101 (10) | 0.0030 (12) |
C1B | 0.045 (3) | 0.041 (2) | 0.0322 (18) | 0.0155 (17) | 0.0051 (13) | 0.0075 (16) |
C2B | 0.035 (3) | 0.042 (3) | 0.037 (3) | 0.0146 (16) | 0.0055 (14) | 0.0038 (15) |
C3B | 0.036 (2) | 0.066 (3) | 0.033 (2) | 0.0201 (18) | −0.0036 (13) | 0.0001 (15) |
C4B | 0.035 (2) | 0.076 (3) | 0.041 (3) | 0.0251 (18) | −0.0009 (14) | 0.0052 (17) |
C5B | 0.042 (5) | 0.067 (8) | 0.058 (7) | 0.027 (3) | 0.013 (2) | 0.0044 (18) |
C6B | 0.053 (3) | 0.050 (2) | 0.034 (2) | 0.0181 (19) | 0.0106 (16) | 0.0026 (16) |
C11B | 0.0470 (18) | 0.0352 (18) | 0.0308 (16) | 0.0150 (15) | 0.0065 (13) | 0.0021 (13) |
C12B | 0.0509 (19) | 0.047 (2) | 0.0294 (17) | 0.0183 (16) | 0.0047 (13) | 0.0010 (13) |
C13B | 0.061 (2) | 0.044 (2) | 0.031 (2) | 0.0213 (19) | 0.0043 (16) | 0.0052 (17) |
C21B | 0.038 (2) | 0.050 (2) | 0.0244 (18) | 0.0148 (16) | 0.0016 (12) | 0.0011 (17) |
C22B | 0.053 (3) | 0.068 (3) | 0.0356 (19) | 0.0277 (19) | 0.0081 (15) | 0.0062 (18) |
O11B | 0.0596 (15) | 0.0717 (16) | 0.0205 (13) | 0.0356 (14) | 0.0095 (10) | 0.0109 (10) |
O12B | 0.065 (2) | 0.067 (2) | 0.0358 (18) | 0.0230 (13) | 0.0127 (11) | 0.0117 (11) |
O21B | 0.0390 (18) | 0.065 (2) | 0.0256 (12) | 0.0242 (12) | 0.0025 (9) | 0.0026 (12) |
C1C | 0.0422 (13) | 0.0402 (14) | 0.0339 (13) | 0.0144 (11) | 0.0065 (10) | 0.0016 (10) |
C2C | 0.0377 (13) | 0.0492 (15) | 0.0359 (13) | 0.0157 (12) | 0.0068 (10) | 0.0019 (11) |
C3C | 0.0438 (15) | 0.084 (2) | 0.0449 (15) | 0.0272 (14) | 0.0041 (12) | 0.0077 (14) |
C4C | 0.0408 (15) | 0.093 (2) | 0.0596 (18) | 0.0310 (15) | 0.0026 (13) | 0.0077 (15) |
C5C | 0.0442 (15) | 0.074 (2) | 0.0641 (18) | 0.0273 (14) | 0.0196 (13) | 0.0104 (14) |
C6C | 0.0549 (16) | 0.0540 (16) | 0.0412 (14) | 0.0224 (13) | 0.0181 (12) | 0.0058 (12) |
C11C | 0.0434 (14) | 0.0404 (14) | 0.0349 (13) | 0.0150 (11) | 0.0075 (10) | 0.0002 (10) |
C12C | 0.0526 (15) | 0.0554 (16) | 0.0304 (13) | 0.0200 (13) | 0.0096 (11) | 0.0026 (11) |
C13C | 0.0586 (16) | 0.0447 (15) | 0.0285 (13) | 0.0172 (13) | 0.0053 (11) | 0.0018 (10) |
C21C | 0.0424 (13) | 0.0601 (16) | 0.0258 (12) | 0.0208 (12) | 0.0052 (9) | 0.0087 (10) |
C22C | 0.0438 (14) | 0.0627 (16) | 0.0326 (13) | 0.0208 (13) | 0.0068 (10) | 0.0040 (11) |
O11C | 0.0586 (11) | 0.0858 (14) | 0.0307 (9) | 0.0270 (10) | 0.0060 (8) | 0.0133 (8) |
O12C | 0.0601 (11) | 0.0692 (12) | 0.0342 (9) | 0.0269 (10) | 0.0106 (8) | 0.0026 (8) |
O21C | 0.0373 (9) | 0.0726 (12) | 0.0267 (8) | 0.0223 (8) | 0.0026 (6) | 0.0032 (7) |
Geometric parameters (Å, º) top
C1A—C6A | 1.388 (4) | C12C—C13C | 1.468 (3) |
C1A—C2A | 1.402 (6) | C12C—H12C | 0.9500 |
C1A—C11A | 1.471 (5) | C13C—O12C | 1.254 (2) |
C2A—O21A | 1.366 (3) | C13C—O11C | 1.293 (2) |
C2A—C3A | 1.395 (5) | C21C—O21C | 1.436 (2) |
C3A—C4A | 1.372 (4) | C21C—C22C | 1.501 (3) |
C3A—H3A | 0.9500 | C21C—H21E | 0.9900 |
C4A—C5A | 1.395 (5) | C21C—H21F | 0.9900 |
C4A—H4A | 0.9500 | C22C—H22G | 0.9800 |
C5A—C6A | 1.365 (5) | C22C—H22H | 0.9800 |
C5A—H5A | 0.9500 | C22C—H22I | 0.9800 |
C6A—H6A | 0.9500 | O11C—H1C | 0.8400 |
C11A—C12A | 1.330 (4) | C1D—C2D | 1.3865 |
C11A—H11A | 0.9500 | C1D—C6D | 1.3961 |
C12A—C13A | 1.461 (5) | C1D—C11D | 1.4980 |
C12A—H12A | 0.9500 | C2D—O21D | 1.3716 |
C13A—O12A | 1.261 (4) | C2D—C3D | 1.4117 |
C13A—O11A | 1.266 (4) | C3D—C4D | 1.3884 |
C21A—O21A | 1.449 (4) | C3D—H3D | 0.9500 |
C21A—C22A | 1.497 (4) | C4D—C5D | 1.3674 |
C21A—H21A | 0.9900 | C4D—H4D | 0.9500 |
C21A—H21B | 0.9900 | C5D—C6D | 1.3890 |
C22A—H22A | 0.9800 | C5D—H5D | 0.9500 |
C22A—H22B | 0.9800 | C6D—H6D | 0.9500 |
C22A—H22C | 0.9800 | C11D—C12D | 1.5394 |
O11A—H1A | 0.8400 | C11D—C12E | 1.6166 |
C1B—C6B | 1.389 (5) | C11D—H11D | 1.0000 |
C1B—C2B | 1.412 (5) | C12D—C13D | 1.5337 |
C1B—C11B | 1.464 (4) | C12D—C11E | 1.6083 |
C2B—O21B | 1.365 (3) | C12D—H12D | 1.0000 |
C2B—C3B | 1.383 (4) | C13D—O12D | 1.2148 |
C3B—C4B | 1.372 (4) | C13D—O11D | 1.3233 |
C3B—H3B | 0.9500 | C21D—O21D | 1.4229 |
C4B—C5B | 1.386 (4) | C21D—C22D | 1.5150 |
C4B—H4B | 0.9500 | C21D—H21G | 0.9900 |
C5B—C6B | 1.370 (5) | C21D—H21H | 0.9900 |
C5B—H5B | 0.9500 | C22D—H22J | 0.9800 |
C6B—H6B | 0.9500 | C22D—H22K | 0.9800 |
C11B—C12B | 1.339 (3) | C22D—H22L | 0.9800 |
C11B—H11B | 0.9500 | O11D—H1D | 0.8400 |
C12B—C13B | 1.459 (4) | C1E—C2E | 1.3829 |
C12B—H12B | 0.9500 | C1E—C6E | 1.3919 |
C13B—O12B | 1.257 (3) | C1E—C11E | 1.5117 |
C13B—O11B | 1.283 (3) | C2E—O21E | 1.3878 |
C21B—O21B | 1.437 (4) | C2E—C3E | 1.3985 |
C21B—C22B | 1.496 (3) | C3E—C4E | 1.3933 |
C21B—H21C | 0.9900 | C3E—H3E | 0.9500 |
C21B—H21D | 0.9900 | C4E—C5E | 1.3664 |
C22B—H22D | 0.9800 | C4E—H4E | 0.9500 |
C22B—H22E | 0.9800 | C5E—C6E | 1.3866 |
C22B—H22F | 0.9800 | C5E—H5E | 0.9500 |
O11B—H1B | 0.8400 | C6E—H6E | 0.9500 |
C1C—C6C | 1.401 (3) | C11E—C12E | 1.5393 |
C1C—C2C | 1.403 (3) | C11E—H11F | 1.0000 |
C1C—C11C | 1.462 (3) | C12E—C13E | 1.5245 |
C2C—O21C | 1.366 (2) | C12E—H12E | 1.0000 |
C2C—C3C | 1.391 (3) | C13E—O12E | 1.2245 |
C3C—C4C | 1.378 (3) | C13E—O11E | 1.3047 |
C3C—H3C | 0.9500 | C21E—O21E | 1.4391 |
C4C—C5C | 1.375 (3) | C21E—C22E | 1.5213 |
C4C—H4C | 0.9500 | C21E—H21I | 0.9900 |
C5C—C6C | 1.373 (3) | C21E—H21J | 0.9900 |
C5C—H5C | 0.9500 | C22E—H22M | 0.9800 |
C6C—H6C | 0.9500 | C22E—H22N | 0.9800 |
C11C—C12C | 1.329 (3) | C22E—H22O | 0.9800 |
C11C—H11C | 0.9500 | O11E—H1E | 0.8400 |
| | | |
C6A—C1A—C2A | 117.8 (4) | O21C—C21C—C22C | 106.88 (16) |
C6A—C1A—C11A | 122.5 (4) | O21C—C21C—H21E | 110.3 |
C2A—C1A—C11A | 119.7 (3) | C22C—C21C—H21E | 110.3 |
O21A—C2A—C3A | 123.3 (5) | O21C—C21C—H21F | 110.3 |
O21A—C2A—C1A | 116.3 (4) | C22C—C21C—H21F | 110.3 |
C3A—C2A—C1A | 120.4 (3) | H21E—C21C—H21F | 108.6 |
C4A—C3A—C2A | 120.1 (4) | C21C—C22C—H22G | 109.5 |
C4A—C3A—H3A | 119.9 | C21C—C22C—H22H | 109.5 |
C2A—C3A—H3A | 119.9 | H22G—C22C—H22H | 109.5 |
C3A—C4A—C5A | 119.9 (3) | C21C—C22C—H22I | 109.5 |
C3A—C4A—H4A | 120.0 | H22G—C22C—H22I | 109.5 |
C5A—C4A—H4A | 120.0 | H22H—C22C—H22I | 109.5 |
C6A—C5A—C4A | 119.6 (4) | C13C—O11C—H1C | 109.5 |
C6A—C5A—H5A | 120.2 | C2C—O21C—C21C | 118.50 (15) |
C4A—C5A—H5A | 120.2 | C2D—C1D—C6D | 117.6 |
C5A—C6A—C1A | 122.1 (5) | C2D—C1D—C11D | 116.5 |
C5A—C6A—H6A | 118.9 | C6D—C1D—C11D | 125.3 |
C1A—C6A—H6A | 118.9 | O21D—C2D—C1D | 115.0 |
C12A—C11A—C1A | 127.0 (3) | O21D—C2D—C3D | 124.0 |
C12A—C11A—H11A | 116.5 | C1D—C2D—C3D | 121.0 |
C1A—C11A—H11A | 116.5 | C4D—C3D—C2D | 118.8 |
C11A—C12A—C13A | 122.4 (3) | C4D—C3D—H3D | 120.6 |
C11A—C12A—H12A | 118.8 | C2D—C3D—H3D | 120.6 |
C13A—C12A—H12A | 118.8 | C5D—C4D—C3D | 121.6 |
O12A—C13A—O11A | 125.0 (4) | C5D—C4D—H4D | 119.2 |
O12A—C13A—C12A | 119.5 (3) | C3D—C4D—H4D | 119.2 |
O11A—C13A—C12A | 115.5 (3) | C4D—C5D—C6D | 118.6 |
O21A—C21A—C22A | 106.3 (4) | C4D—C5D—H5D | 120.7 |
O21A—C21A—H21A | 110.5 | C6D—C5D—H5D | 120.7 |
C22A—C21A—H21A | 110.5 | C5D—C6D—C1D | 122.5 |
O21A—C21A—H21B | 110.5 | C5D—C6D—H6D | 118.7 |
C22A—C21A—H21B | 110.5 | C1D—C6D—H6D | 118.7 |
H21A—C21A—H21B | 108.7 | C1D—C11D—C12D | 119.2 |
C21A—C22A—H22A | 109.5 | C1D—C11D—C12E | 116.5 |
C21A—C22A—H22B | 109.5 | C12D—C11D—C12E | 89.6 |
H22A—C22A—H22B | 109.5 | C1D—C11D—H11D | 110.0 |
C21A—C22A—H22C | 109.5 | C12D—C11D—H11D | 110.0 |
H22A—C22A—H22C | 109.5 | C12E—C11D—H11D | 110.0 |
H22B—C22A—H22C | 109.5 | C13D—C12D—C11D | 114.6 |
C13A—O11A—H1A | 109.5 | C13D—C12D—C11E | 112.4 |
C2A—O21A—C21A | 118.9 (3) | C11D—C12D—C11E | 90.4 |
C6B—C1B—C2B | 117.8 (3) | C13D—C12D—H12D | 112.6 |
C6B—C1B—C11B | 121.9 (4) | C11D—C12D—H12D | 112.6 |
C2B—C1B—C11B | 120.3 (3) | C11E—C12D—H12D | 112.6 |
O21B—C2B—C3B | 123.6 (4) | O12D—C13D—O11D | 122.4 |
O21B—C2B—C1B | 116.1 (3) | O12D—C13D—C12D | 124.0 |
C3B—C2B—C1B | 120.4 (3) | O11D—C13D—C12D | 113.0 |
C4B—C3B—C2B | 119.9 (3) | O21D—C21D—C22D | 107.7 |
C4B—C3B—H3B | 120.0 | O21D—C21D—H21G | 110.2 |
C2B—C3B—H3B | 120.0 | C22D—C21D—H21G | 110.2 |
C3B—C4B—C5B | 120.7 (3) | O21D—C21D—H21H | 110.2 |
C3B—C4B—H4B | 119.6 | C22D—C21D—H21H | 110.2 |
C5B—C4B—H4B | 119.6 | H21G—C21D—H21H | 108.5 |
C6B—C5B—C4B | 119.4 (5) | C21D—C22D—H22J | 109.5 |
C6B—C5B—H5B | 120.3 | C21D—C22D—H22K | 109.5 |
C4B—C5B—H5B | 120.3 | H22J—C22D—H22K | 109.5 |
C5B—C6B—C1B | 121.7 (4) | C21D—C22D—H22L | 109.5 |
C5B—C6B—H6B | 119.1 | H22J—C22D—H22L | 109.5 |
C1B—C6B—H6B | 119.1 | H22K—C22D—H22L | 109.5 |
C12B—C11B—C1B | 126.5 (3) | C13D—O11D—H1D | 109.5 |
C12B—C11B—H11B | 116.7 | C2D—O21D—C21D | 118.0 |
C1B—C11B—H11B | 116.7 | C2E—C1E—C6E | 118.5 |
C11B—C12B—C13B | 121.9 (3) | C2E—C1E—C11E | 115.6 |
C11B—C12B—H12B | 119.1 | C6E—C1E—C11E | 124.9 |
C13B—C12B—H12B | 119.1 | C1E—C2E—O21E | 115.2 |
O12B—C13B—O11B | 124.2 (3) | C1E—C2E—C3E | 120.7 |
O12B—C13B—C12B | 121.4 (3) | O21E—C2E—C3E | 124.1 |
O11B—C13B—C12B | 114.3 (3) | C4E—C3E—C2E | 119.0 |
O21B—C21B—C22B | 107.0 (3) | C4E—C3E—H3E | 120.5 |
O21B—C21B—H21C | 110.3 | C2E—C3E—H3E | 120.5 |
C22B—C21B—H21C | 110.3 | C5E—C4E—C3E | 121.3 |
O21B—C21B—H21D | 110.3 | C5E—C4E—H4E | 119.4 |
C22B—C21B—H21D | 110.3 | C3E—C4E—H4E | 119.4 |
H21C—C21B—H21D | 108.6 | C4E—C5E—C6E | 119.0 |
C21B—C22B—H22D | 109.5 | C4E—C5E—H5E | 120.5 |
C21B—C22B—H22E | 109.5 | C6E—C5E—H5E | 120.5 |
H22D—C22B—H22E | 109.5 | C5E—C6E—C1E | 121.6 |
C21B—C22B—H22F | 109.5 | C5E—C6E—H6E | 119.2 |
H22D—C22B—H22F | 109.5 | C1E—C6E—H6E | 119.2 |
H22E—C22B—H22F | 109.5 | C1E—C11E—C12E | 119.6 |
C13B—O11B—H1B | 109.5 | C1E—C11E—C12D | 116.7 |
C2B—O21B—C21B | 118.1 (3) | C12E—C11E—C12D | 89.9 |
C6C—C1C—C2C | 117.9 (2) | C1E—C11E—H11F | 109.7 |
C6C—C1C—C11C | 122.2 (2) | C12E—C11E—H11F | 109.7 |
C2C—C1C—C11C | 119.83 (19) | C12D—C11E—H11F | 109.7 |
O21C—C2C—C3C | 123.5 (2) | C13E—C12E—C11E | 115.4 |
O21C—C2C—C1C | 116.24 (19) | C13E—C12E—C11D | 112.1 |
C3C—C2C—C1C | 120.3 (2) | C11E—C12E—C11D | 90.1 |
C4C—C3C—C2C | 119.7 (2) | C13E—C12E—H12E | 112.5 |
C4C—C3C—H3C | 120.2 | C11E—C12E—H12E | 112.5 |
C2C—C3C—H3C | 120.2 | C11D—C12E—H12E | 112.5 |
C5C—C4C—C3C | 121.2 (2) | O12E—C13E—O11E | 123.8 |
C5C—C4C—H4C | 119.4 | O12E—C13E—C12E | 123.0 |
C3C—C4C—H4C | 119.4 | O11E—C13E—C12E | 112.5 |
C6C—C5C—C4C | 119.3 (2) | O21E—C21E—C22E | 107.3 |
C6C—C5C—H5C | 120.3 | O21E—C21E—H21I | 110.3 |
C4C—C5C—H5C | 120.3 | C22E—C21E—H21I | 110.3 |
C5C—C6C—C1C | 121.6 (2) | O21E—C21E—H21J | 110.3 |
C5C—C6C—H6C | 119.2 | C22E—C21E—H21J | 110.3 |
C1C—C6C—H6C | 119.2 | H21I—C21E—H21J | 108.5 |
C12C—C11C—C1C | 126.7 (2) | C21E—C22E—H22M | 109.5 |
C12C—C11C—H11C | 116.6 | C21E—C22E—H22N | 109.5 |
C1C—C11C—H11C | 116.6 | H22M—C22E—H22N | 109.5 |
C11C—C12C—C13C | 122.2 (2) | C21E—C22E—H22O | 109.5 |
C11C—C12C—H12C | 118.9 | H22M—C22E—H22O | 109.5 |
C13C—C12C—H12C | 118.9 | H22N—C22E—H22O | 109.5 |
O12C—C13C—O11C | 123.3 (2) | C13E—O11E—H1E | 109.5 |
O12C—C13C—C12C | 121.7 (2) | C2E—O21E—C21E | 117.6 |
O11C—C13C—C12C | 115.0 (2) | | |
| | | |
C6A—C1A—C2A—O21A | 179.9 (4) | C6D—C1D—C2D—C3D | −1.6 |
C11A—C1A—C2A—O21A | 0.0 (6) | C11D—C1D—C2D—C3D | −172.7 |
C6A—C1A—C2A—C3A | 0.0 (6) | O21D—C2D—C3D—C4D | −179.8 |
C11A—C1A—C2A—C3A | −179.8 (4) | C1D—C2D—C3D—C4D | 1.7 |
O21A—C2A—C3A—C4A | 179.1 (4) | C2D—C3D—C4D—C5D | −1.5 |
C1A—C2A—C3A—C4A | −1.0 (7) | C3D—C4D—C5D—C6D | 1.1 |
C2A—C3A—C4A—C5A | 1.7 (8) | C4D—C5D—C6D—C1D | −1.0 |
C3A—C4A—C5A—C6A | −1.4 (8) | C2D—C1D—C6D—C5D | 1.3 |
C4A—C5A—C6A—C1A | 0.4 (8) | C11D—C1D—C6D—C5D | 171.5 |
C2A—C1A—C6A—C5A | 0.3 (7) | C2D—C1D—C11D—C12D | −176.6 |
C11A—C1A—C6A—C5A | −179.8 (4) | C6D—C1D—C11D—C12D | 13.1 |
C6A—C1A—C11A—C12A | 1.7 (6) | C2D—C1D—C11D—C12E | 77.8 |
C2A—C1A—C11A—C12A | −178.5 (4) | C6D—C1D—C11D—C12E | −92.6 |
C1A—C11A—C12A—C13A | 179.4 (4) | C1D—C11D—C12D—C13D | 125.2 |
C11A—C12A—C13A—O12A | −1.2 (6) | C12E—C11D—C12D—C13D | −114.3 |
C11A—C12A—C13A—O11A | 179.0 (3) | C1D—C11D—C12D—C11E | −119.8 |
C3A—C2A—O21A—C21A | 0.6 (6) | C12E—C11D—C12D—C11E | 0.7 |
C1A—C2A—O21A—C21A | −179.2 (3) | C11D—C12D—C13D—O12D | 31.8 |
C22A—C21A—O21A—C2A | 175.1 (3) | C11E—C12D—C13D—O12D | −69.5 |
C6B—C1B—C2B—O21B | 179.5 (4) | C11D—C12D—C13D—O11D | −157.0 |
C11B—C1B—C2B—O21B | 1.6 (6) | C11E—C12D—C13D—O11D | 101.6 |
C6B—C1B—C2B—C3B | −0.8 (7) | C1D—C2D—O21D—C21D | −169.1 |
C11B—C1B—C2B—C3B | −178.8 (4) | C3D—C2D—O21D—C21D | 12.3 |
O21B—C2B—C3B—C4B | −179.7 (5) | C22D—C21D—O21D—C2D | 174.3 |
C1B—C2B—C3B—C4B | 0.6 (8) | C6E—C1E—C2E—O21E | 179.2 |
C2B—C3B—C4B—C5B | −0.7 (9) | C11E—C1E—C2E—O21E | −11.3 |
C3B—C4B—C5B—C6B | 1.0 (8) | C6E—C1E—C2E—C3E | 0.3 |
C4B—C5B—C6B—C1B | −1.3 (7) | C11E—C1E—C2E—C3E | 169.8 |
C2B—C1B—C6B—C5B | 1.1 (7) | C1E—C2E—C3E—C4E | 0.1 |
C11B—C1B—C6B—C5B | 179.1 (4) | O21E—C2E—C3E—C4E | −178.7 |
C6B—C1B—C11B—C12B | 8.6 (6) | C2E—C3E—C4E—C5E | 0.0 |
C2B—C1B—C11B—C12B | −173.5 (3) | C3E—C4E—C5E—C6E | −0.5 |
C1B—C11B—C12B—C13B | −179.1 (4) | C4E—C5E—C6E—C1E | 0.9 |
C11B—C12B—C13B—O12B | 5.7 (6) | C2E—C1E—C6E—C5E | −0.8 |
C11B—C12B—C13B—O11B | −173.1 (3) | C11E—C1E—C6E—C5E | −169.2 |
C3B—C2B—O21B—C21B | −1.6 (6) | C2E—C1E—C11E—C12E | −176.1 |
C1B—C2B—O21B—C21B | 178.0 (3) | C6E—C1E—C11E—C12E | −7.4 |
C22B—C21B—O21B—C2B | −176.4 (3) | C2E—C1E—C11E—C12D | −69.7 |
C6C—C1C—C2C—O21C | 179.7 (2) | C6E—C1E—C11E—C12D | 99.1 |
C11C—C1C—C2C—O21C | −1.6 (3) | C13D—C12D—C11E—C1E | −7.3 |
C6C—C1C—C2C—C3C | −0.4 (3) | C11D—C12D—C11E—C1E | −124.2 |
C11C—C1C—C2C—C3C | 178.3 (2) | C13D—C12D—C11E—C12E | 116.2 |
O21C—C2C—C3C—C4C | 179.7 (2) | C11D—C12D—C11E—C12E | −0.7 |
C1C—C2C—C3C—C4C | −0.1 (4) | C1E—C11E—C12E—C13E | −123.6 |
C2C—C3C—C4C—C5C | 0.7 (4) | C12D—C11E—C12E—C13E | 115.4 |
C3C—C4C—C5C—C6C | −0.7 (4) | C1E—C11E—C12E—C11D | 121.7 |
C4C—C5C—C6C—C1C | 0.1 (4) | C12D—C11E—C12E—C11D | 0.7 |
C2C—C1C—C6C—C5C | 0.4 (3) | C1D—C11D—C12E—C13E | 4.5 |
C11C—C1C—C6C—C5C | −178.3 (2) | C12D—C11D—C12E—C13E | −118.3 |
C6C—C1C—C11C—C12C | 2.3 (4) | C1D—C11D—C12E—C11E | 122.1 |
C2C—C1C—C11C—C12C | −176.4 (2) | C12D—C11D—C12E—C11E | −0.7 |
C1C—C11C—C12C—C13C | 178.4 (2) | C11E—C12E—C13E—O12E | −23.8 |
C11C—C12C—C13C—O12C | 4.8 (4) | C11D—C12E—C13E—O12E | 77.5 |
C11C—C12C—C13C—O11C | −175.5 (2) | C11E—C12E—C13E—O11E | 165.0 |
C3C—C2C—O21C—C21C | −1.5 (3) | C11D—C12E—C13E—O11E | −93.7 |
C1C—C2C—O21C—C21C | 178.32 (19) | C1E—C2E—O21E—C21E | 165.9 |
C22C—C21C—O21C—C2C | −175.72 (19) | C3E—C2E—O21E—C21E | −15.2 |
C6D—C1D—C2D—O21D | 179.8 | C22E—C21E—O21E—C2E | −171.1 |
C11D—C1D—C2D—O21D | 8.7 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11A—H1A···O12Ai | 0.84 | 1.70 | 2.522 (5) | 166 |
O11B—H1B···O12Cii | 0.84 | 1.76 | 2.590 (3) | 170 |
O11C—H1C···O12Bii | 0.84 | 1.78 | 2.607 (4) | 168 |
O11E—H1E···O12Cii | 0.84 | 2.09 | 2.823 (6) | 146 |
O11C—H1C···O12Eii | 0.84 | 1.92 | 2.75 (2) | 169 |
O11D—H1D···O12Di | 0.84 | 2.33 | 3.094 (11) | 152 |
O11D—H1D···O12Ai | 0.84 | 2.18 | 2.929 (6) | 148 |
O11A—H1A···O12Di | 0.84 | 1.84 | 2.671 (6) | 169 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z+1. |
(rd24hlts) (
E)-3-(2-Ethoxyphenyl)propenoic acid and
trans-2,4-bis(2-ethoxyphenyl)-
trans-1,3-cyclobutane-dicarboxylic acid
top
Crystal data top
0.680(C22H24O6)·1.640(C11H12O3) | Z = 2 |
Mr = 576.62 | F(000) = 612 |
Triclinic, P1 | Dx = 1.293 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4919 (13) Å | Cell parameters from 864 reflections |
b = 10.9148 (17) Å | θ = 2.6–27.2° |
c = 17.372 (3) Å | µ = 0.09 mm−1 |
α = 96.027 (3)° | T = 173 K |
β = 91.772 (3)° | Irregular, white |
γ = 111.956 (3)° | 0.45 × 0.24 × 0.14 mm |
V = 1480.8 (4) Å3 | |
Data collection top
CCD area detector diffractometer | 2825 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 25.5°, θmin = 1.2° |
phi and ω scans | h = −10→10 |
8447 measured reflections | k = −13→7 |
5471 independent reflections | l = −21→19 |
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.172 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.070P)2 + 0.1699P] where P = (Fo2 + 2Fc2)/3 |
5471 reflections | (Δ/σ)max < 0.001 |
409 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
Crystal data top
0.680(C22H24O6)·1.640(C11H12O3) | γ = 111.956 (3)° |
Mr = 576.62 | V = 1480.8 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.4919 (13) Å | Mo Kα radiation |
b = 10.9148 (17) Å | µ = 0.09 mm−1 |
c = 17.372 (3) Å | T = 173 K |
α = 96.027 (3)° | 0.45 × 0.24 × 0.14 mm |
β = 91.772 (3)° | |
Data collection top
CCD area detector diffractometer | 2825 reflections with I > 2σ(I) |
8447 measured reflections | Rint = 0.030 |
5471 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.172 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.19 e Å−3 |
5471 reflections | Δρmin = −0.35 e Å−3 |
409 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 | Occ. (<1) |
C1A | 1.0102 (5) | 0.0233 (4) | 0.2193 (2) | 0.0459 (11)* | 0.320 (4) |
C2A | 1.0033 (5) | 0.0191 (4) | 0.2995 (2) | 0.0459 (11)* | 0.320 (4) |
C3A | 1.1444 (5) | 0.0276 (4) | 0.3445 (2) | 0.0459 (11)* | 0.320 (4) |
H3A | 1.1400 | 0.0270 | 0.3991 | 0.055* | 0.320 (4) |
C4A | 1.2915 (5) | 0.0368 (4) | 0.3103 (2) | 0.0459 (11)* | 0.320 (4) |
H4A | 1.3882 | 0.0417 | 0.3414 | 0.055* | 0.320 (4) |
C5A | 1.3003 (5) | 0.0390 (4) | 0.2316 (2) | 0.0459 (11)* | 0.320 (4) |
H5A | 1.4023 | 0.0450 | 0.2083 | 0.055* | 0.320 (4) |
C6A | 1.1617 (5) | 0.0326 (4) | 0.1870 (2) | 0.0459 (11)* | 0.320 (4) |
H6A | 1.1687 | 0.0345 | 0.1326 | 0.055* | 0.320 (4) |
C11A | 0.8578 (5) | 0.0102 (4) | 0.1700 (2) | 0.0260 (14) | 0.320 (4) |
H11A | 0.7597 | 0.0046 | 0.1965 | 0.031* | 0.320 (4) |
C12A | 0.8410 (5) | 0.0053 (4) | 0.0927 (2) | 0.0260 (14) | 0.32 |
H12A | 0.9361 | 0.0104 | 0.0639 | 0.031* | 0.320 (4) |
C13A | 0.6829 (5) | −0.0076 (4) | 0.0510 (2) | 0.0459 (11)* | 0.320 (4) |
C21A | 0.8391 (5) | 0.0105 (4) | 0.4111 (2) | 0.0459 (11)* | 0.320 (4) |
H21A | 0.9291 | 0.0910 | 0.4392 | 0.055* | 0.320 (4) |
H21B | 0.8523 | −0.0691 | 0.4282 | 0.055* | 0.320 (4) |
C22A | 0.6671 (5) | 0.0101 (4) | 0.4272 (2) | 0.0459 (11)* | 0.320 (4) |
H22A | 0.6536 | 0.0107 | 0.4830 | 0.069* | 0.320 (4) |
H22B | 0.5792 | −0.0700 | 0.3991 | 0.069* | 0.320 (4) |
H22C | 0.6557 | 0.0893 | 0.4101 | 0.069* | 0.320 (4) |
O11A | 0.6798 (5) | −0.0107 (4) | −0.0225 (2) | 0.0459 (11)* | 0.320 (4) |
H1A | 0.5828 | −0.0183 | −0.0400 | 0.069* | 0.320 (4) |
O12A | 0.5579 (5) | −0.0151 (4) | 0.0905 (2) | 0.0459 (11)* | 0.320 (4) |
O21A | 0.8524 (5) | 0.0096 (4) | 0.3288 (2) | 0.0459 (11)* | 0.320 (4) |
C1B | 0.7683 (6) | 0.3328 (4) | 0.1230 (3) | 0.0459 (11)* | 0.320 (4) |
C2B | 0.7682 (6) | 0.3202 (4) | 0.0417 (3) | 0.0459 (11)* | 0.320 (4) |
C3B | 0.6297 (6) | 0.3173 (4) | −0.0036 (3) | 0.0459 (11)* | 0.320 (4) |
H3B | 0.6304 | 0.3089 | −0.0585 | 0.055* | 0.320 (4) |
C4B | 0.4908 (6) | 0.3269 (4) | 0.0315 (3) | 0.0459 (11)* | 0.320 (4) |
H4B | 0.3959 | 0.3252 | 0.0003 | 0.055* | 0.320 (4) |
C5B | 0.4877 (6) | 0.3389 (4) | 0.1111 (3) | 0.0459 (11)* | 0.320 (4) |
H5B | 0.3912 | 0.3450 | 0.1349 | 0.055* | 0.320 (4) |
C6B | 0.6262 (6) | 0.3421 (4) | 0.1559 (3) | 0.0459 (11)* | 0.320 (4) |
H6B | 0.6241 | 0.3508 | 0.2108 | 0.055* | 0.320 (4) |
C11B | 0.9176 (6) | 0.3425 (4) | 0.1719 (3) | 0.029 (2) | 0.320 (4) |
H11B | 1.0165 | 0.3484 | 0.1459 | 0.035* | 0.320 (4) |
C12B | 0.9303 (6) | 0.3440 (4) | 0.2491 (3) | 0.033 (2) | 0.320 (4) |
H12B | 0.8343 | 0.3390 | 0.2772 | 0.040* | 0.320 (4) |
C13B | 1.0858 (6) | 0.3529 (4) | 0.2917 (3) | 0.0459 (11)* | 0.320 (4) |
C21B | 0.9137 (6) | 0.2925 (4) | −0.0712 (3) | 0.0459 (11)* | 0.320 (4) |
H21C | 0.9069 | 0.3700 | −0.0939 | 0.055* | 0.320 (4) |
H21D | 0.8157 | 0.2118 | −0.0936 | 0.055* | 0.320 (4) |
C22B | 1.0774 (6) | 0.2770 (4) | −0.0882 (3) | 0.0459 (11)* | 0.320 (4) |
H22D | 1.0836 | 0.2634 | −0.1445 | 0.069* | 0.320 (4) |
H22E | 1.0825 | 0.2000 | −0.0654 | 0.069* | 0.320 (4) |
H22F | 1.1733 | 0.3575 | −0.0658 | 0.069* | 0.320 (4) |
O11B | 1.0738 (6) | 0.3400 (4) | 0.3644 (3) | 0.0459 (11)* | 0.320 (4) |
H1B | 1.1681 | 0.3464 | 0.3846 | 0.069* | 0.320 (4) |
O12B | 1.2199 (6) | 0.3713 (4) | 0.2570 (3) | 0.0459 (11)* | 0.320 (4) |
O21B | 0.9109 (6) | 0.3120 (4) | 0.0116 (3) | 0.0459 (11)* | 0.320 (4) |
C1C | 0.2290 (3) | 0.6603 (3) | 0.42850 (15) | 0.0361 (7) | |
C2C | 0.2347 (3) | 0.6616 (3) | 0.34800 (15) | 0.0409 (7) | |
C3C | 0.0909 (4) | 0.6494 (4) | 0.30222 (18) | 0.0622 (10) | |
H3C | 0.0943 | 0.6473 | 0.2475 | 0.075* | |
C4C | −0.0566 (4) | 0.6403 (4) | 0.33658 (19) | 0.0687 (11) | |
H4C | −0.1544 | 0.6319 | 0.3051 | 0.082* | |
C5C | −0.0644 (4) | 0.6431 (3) | 0.41581 (19) | 0.0584 (9) | |
H5C | −0.1660 | 0.6384 | 0.4391 | 0.070* | |
C6C | 0.0777 (4) | 0.6531 (3) | 0.46085 (16) | 0.0448 (8) | |
H6C | 0.0725 | 0.6550 | 0.5155 | 0.054* | |
C11C | 0.3762 (3) | 0.6628 (3) | 0.47506 (14) | 0.0355 (7) | |
H11C | 0.4760 | 0.6724 | 0.4490 | 0.043* | |
C12C | 0.3836 (4) | 0.6530 (3) | 0.55101 (15) | 0.0419 (8) | |
H12C | 0.2883 | 0.6487 | 0.5794 | 0.050* | |
C13C | 0.5352 (4) | 0.6487 (3) | 0.59173 (15) | 0.0405 (7) | |
C21C | 0.4002 (3) | 0.6823 (3) | 0.23676 (14) | 0.0405 (7) | |
H21E | 0.3794 | 0.7608 | 0.2227 | 0.049* | |
H21F | 0.3155 | 0.6014 | 0.2063 | 0.049* | |
C22C | 0.5766 (3) | 0.6944 (3) | 0.21995 (15) | 0.0459 (8) | |
H22G | 0.6593 | 0.7707 | 0.2534 | 0.069* | |
H22H | 0.5937 | 0.7075 | 0.1654 | 0.069* | |
H22I | 0.5925 | 0.6129 | 0.2300 | 0.069* | |
O11C | 0.5129 (2) | 0.6252 (2) | 0.66392 (10) | 0.0553 (6) | |
H1C | 0.6028 | 0.6240 | 0.6847 | 0.083* | |
O12C | 0.6690 (2) | 0.6644 (2) | 0.56122 (10) | 0.0492 (6) | |
O21C | 0.3863 (2) | 0.6741 (2) | 0.31848 (9) | 0.0429 (5) | |
C1D | 1.0114 (5) | 0.0400 (4) | 0.2308 (2) | 0.0363 (11) | 0.680 (4) |
C2D | 0.9970 (5) | 0.0023 (4) | 0.3053 (2) | 0.0322 (10) | 0.680 (4) |
C3D | 1.1266 (5) | −0.0248 (5) | 0.3425 (2) | 0.0414 (12) | 0.680 (4) |
H3D | 1.1158 | −0.0505 | 0.3933 | 0.050* | 0.680 (4) |
C4D | 1.2710 (6) | −0.0134 (5) | 0.3042 (3) | 0.0462 (13) | 0.680 (4) |
H4D | 1.3601 | −0.0307 | 0.3293 | 0.055* | 0.680 (4) |
C5D | 1.2879 (6) | 0.0223 (5) | 0.2304 (3) | 0.0457 (12) | 0.680 (4) |
H5D | 1.3864 | 0.0277 | 0.2042 | 0.055* | 0.680 (4) |
C6D | 1.1590 (6) | 0.0503 (5) | 0.1947 (3) | 0.0473 (12) | 0.680 (4) |
H6D | 1.1720 | 0.0773 | 0.1443 | 0.057* | 0.680 (4) |
C11D | 0.8789 (5) | 0.0861 (5) | 0.2007 (2) | 0.0396 (12) | 0.680 (4) |
H11D | 0.7631 | 0.0222 | 0.2099 | 0.048* | 0.680 (4) |
C12D | 0.8803 (5) | 0.1194 (4) | 0.1167 (2) | 0.0400 (12) | 0.680 (4) |
H12D | 0.9817 | 0.1150 | 0.0906 | 0.048* | 0.680 (4) |
C13D | 0.7140 (6) | 0.0450 (5) | 0.0665 (2) | 0.0385 (11) | 0.680 (4) |
C21D | 0.8376 (5) | −0.0210 (5) | 0.4179 (2) | 0.0420 (12) | 0.680 (4) |
H21G | 0.9337 | 0.0511 | 0.4489 | 0.050* | 0.680 (4) |
H21H | 0.8423 | −0.1075 | 0.4274 | 0.050* | 0.680 (4) |
C22D | 0.6712 (5) | −0.0145 (5) | 0.4406 (2) | 0.0424 (12) | 0.680 (4) |
H22J | 0.6718 | 0.0741 | 0.4351 | 0.064* | 0.680 (4) |
H22K | 0.6559 | −0.0315 | 0.4947 | 0.064* | 0.680 (4) |
H22L | 0.5776 | −0.0818 | 0.4068 | 0.064* | 0.680 (4) |
O11D | 0.7335 (4) | 0.0386 (3) | −0.00881 (16) | 0.0438 (8) | 0.680 (4) |
H1D | 0.6392 | −0.0065 | −0.0334 | 0.066* | 0.680 (4) |
O12D | 0.5755 (4) | 0.0105 (3) | 0.09238 (18) | 0.0482 (9) | 0.680 (4) |
O21D | 0.8491 (3) | −0.0064 (3) | 0.33750 (16) | 0.0355 (8) | 0.680 (4) |
C1E | 0.7733 (5) | 0.3205 (4) | 0.1170 (2) | 0.0340 (10) | 0.680 (4) |
C2E | 0.7806 (5) | 0.3420 (4) | 0.0397 (2) | 0.0292 (10) | 0.680 (4) |
C3E | 0.6503 (6) | 0.3651 (5) | 0.0009 (3) | 0.0482 (13) | 0.680 (4) |
H3E | 0.6550 | 0.3779 | −0.0524 | 0.058* | 0.680 (4) |
C4E | 0.5137 (6) | 0.3690 (6) | 0.0414 (3) | 0.0561 (15) | 0.680 (4) |
H4E | 0.4247 | 0.3857 | 0.0156 | 0.067* | 0.680 (4) |
C5E | 0.5049 (6) | 0.3493 (5) | 0.1182 (3) | 0.0512 (13) | 0.680 (4) |
H5E | 0.4113 | 0.3531 | 0.1456 | 0.061* | 0.680 (4) |
C6E | 0.6340 (6) | 0.3237 (5) | 0.1555 (3) | 0.0416 (12) | 0.680 (4) |
H6E | 0.6269 | 0.3082 | 0.2083 | 0.050* | 0.680 (4) |
C11E | 0.9036 (5) | 0.2719 (5) | 0.1487 (2) | 0.0355 (12) | 0.680 (4) |
H11E | 1.0205 | 0.3345 | 0.1399 | 0.043* | 0.680 (4) |
C12E | 0.8994 (5) | 0.2389 (5) | 0.2329 (2) | 0.0422 (12) | 0.680 (4) |
H12E | 0.7966 | 0.2424 | 0.2581 | 0.051* | 0.680 (4) |
C13E | 1.0619 (5) | 0.3112 (4) | 0.2842 (2) | 0.0298 (10) | 0.680 (4) |
C21E | 0.9221 (5) | 0.3291 (5) | −0.0771 (2) | 0.0359 (11) | 0.680 (4) |
H21I | 0.9210 | 0.4119 | −0.0951 | 0.043* | 0.680 (4) |
H21J | 0.8192 | 0.2537 | −0.1008 | 0.043* | 0.680 (4) |
C22E | 1.0799 (6) | 0.3072 (5) | −0.1001 (2) | 0.0473 (13) | 0.680 (4) |
H22M | 1.1809 | 0.3840 | −0.0779 | 0.071* | 0.680 (4) |
H22N | 1.0801 | 0.2968 | −0.1568 | 0.071* | 0.680 (4) |
H22O | 1.0814 | 0.2266 | −0.0805 | 0.071* | 0.680 (4) |
O11E | 1.0399 (4) | 0.3009 (3) | 0.35768 (15) | 0.0355 (8) | 0.680 (4) |
H1E | 1.1351 | 0.3277 | 0.3829 | 0.053* | 0.680 (4) |
O12E | 1.2005 (4) | 0.3579 (3) | 0.25795 (17) | 0.0370 (8) | 0.680 (4) |
O21E | 0.9243 (4) | 0.3392 (3) | 0.00591 (16) | 0.0346 (8) | 0.680 (4) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C11A | 0.038 (3) | 0.010 (3) | 0.025 (3) | 0.006 (3) | 0.002 (3) | −0.009 (3) |
C12A | 0.038 (3) | 0.010 (3) | 0.025 (3) | 0.006 (3) | 0.002 (3) | −0.009 (3) |
C11B | 0.044 (6) | 0.012 (5) | 0.026 (5) | 0.006 (5) | 0.009 (4) | −0.007 (4) |
C12B | 0.050 (6) | 0.028 (6) | 0.021 (5) | 0.017 (5) | 0.001 (4) | −0.010 (4) |
C1C | 0.0408 (17) | 0.0375 (18) | 0.0303 (16) | 0.0147 (14) | 0.0073 (13) | 0.0050 (13) |
C2C | 0.0349 (17) | 0.058 (2) | 0.0342 (16) | 0.0210 (16) | 0.0084 (13) | 0.0103 (14) |
C3C | 0.0477 (19) | 0.113 (3) | 0.0391 (18) | 0.043 (2) | 0.0073 (15) | 0.0209 (19) |
C4C | 0.043 (2) | 0.123 (3) | 0.057 (2) | 0.047 (2) | 0.0077 (16) | 0.024 (2) |
C5C | 0.0438 (19) | 0.084 (3) | 0.059 (2) | 0.0335 (19) | 0.0204 (16) | 0.0205 (19) |
C6C | 0.0501 (19) | 0.054 (2) | 0.0377 (17) | 0.0263 (17) | 0.0164 (14) | 0.0106 (15) |
C11C | 0.0373 (16) | 0.0382 (18) | 0.0294 (16) | 0.0137 (14) | 0.0028 (12) | 0.0000 (13) |
C12C | 0.0465 (18) | 0.053 (2) | 0.0277 (16) | 0.0199 (16) | 0.0092 (13) | 0.0053 (14) |
C13C | 0.0518 (19) | 0.0429 (19) | 0.0236 (16) | 0.0148 (16) | 0.0025 (14) | 0.0025 (13) |
C21C | 0.0415 (17) | 0.058 (2) | 0.0251 (15) | 0.0216 (16) | 0.0045 (12) | 0.0073 (14) |
C22C | 0.0397 (17) | 0.062 (2) | 0.0341 (16) | 0.0178 (16) | 0.0044 (13) | 0.0009 (15) |
O11C | 0.0488 (13) | 0.0884 (18) | 0.0293 (12) | 0.0237 (12) | 0.0044 (9) | 0.0183 (11) |
O12C | 0.0480 (13) | 0.0676 (15) | 0.0323 (11) | 0.0224 (11) | 0.0084 (10) | 0.0047 (10) |
O21C | 0.0357 (11) | 0.0703 (15) | 0.0263 (10) | 0.0232 (11) | 0.0042 (8) | 0.0088 (10) |
C1D | 0.033 (2) | 0.037 (3) | 0.044 (3) | 0.016 (2) | 0.0080 (19) | 0.016 (2) |
C2D | 0.035 (2) | 0.029 (2) | 0.034 (2) | 0.013 (2) | 0.0046 (18) | 0.0046 (18) |
C3D | 0.045 (3) | 0.051 (3) | 0.034 (2) | 0.025 (2) | 0.000 (2) | 0.007 (2) |
C4D | 0.041 (3) | 0.052 (3) | 0.052 (3) | 0.027 (3) | −0.004 (2) | 0.000 (2) |
C5D | 0.036 (3) | 0.052 (3) | 0.053 (3) | 0.023 (2) | 0.008 (2) | −0.001 (2) |
C6D | 0.048 (3) | 0.060 (3) | 0.045 (3) | 0.030 (3) | 0.014 (2) | 0.014 (2) |
C11D | 0.040 (2) | 0.054 (3) | 0.031 (2) | 0.022 (2) | 0.0098 (19) | 0.014 (2) |
C12D | 0.043 (3) | 0.055 (3) | 0.028 (2) | 0.025 (2) | 0.0051 (18) | 0.004 (2) |
C13D | 0.057 (3) | 0.043 (3) | 0.027 (2) | 0.028 (3) | 0.017 (2) | 0.013 (2) |
C21D | 0.048 (3) | 0.055 (3) | 0.028 (2) | 0.024 (2) | 0.0018 (19) | 0.008 (2) |
C22D | 0.049 (3) | 0.061 (3) | 0.027 (2) | 0.029 (2) | 0.0079 (19) | 0.013 (2) |
O11D | 0.0371 (18) | 0.055 (2) | 0.0294 (17) | 0.0053 (17) | 0.0042 (13) | 0.0069 (15) |
O12D | 0.057 (2) | 0.045 (2) | 0.0393 (18) | 0.0137 (17) | 0.0191 (15) | 0.0111 (15) |
O21D | 0.0296 (15) | 0.053 (2) | 0.0274 (16) | 0.0171 (14) | 0.0059 (12) | 0.0134 (13) |
C1E | 0.031 (2) | 0.038 (3) | 0.034 (2) | 0.012 (2) | 0.0024 (18) | 0.0142 (19) |
C2E | 0.029 (2) | 0.032 (2) | 0.026 (2) | 0.0115 (19) | −0.0004 (17) | 0.0007 (18) |
C3E | 0.046 (3) | 0.073 (4) | 0.032 (2) | 0.029 (3) | −0.009 (2) | 0.008 (2) |
C4E | 0.042 (3) | 0.082 (4) | 0.055 (3) | 0.036 (3) | −0.005 (2) | 0.011 (3) |
C5E | 0.043 (3) | 0.070 (4) | 0.054 (3) | 0.036 (3) | 0.010 (2) | 0.011 (3) |
C6E | 0.045 (3) | 0.047 (3) | 0.034 (2) | 0.018 (2) | 0.007 (2) | 0.007 (2) |
C11E | 0.033 (2) | 0.044 (3) | 0.028 (2) | 0.012 (2) | −0.0005 (19) | 0.009 (2) |
C12E | 0.042 (3) | 0.065 (4) | 0.028 (2) | 0.029 (3) | 0.0035 (19) | 0.007 (2) |
C13E | 0.043 (3) | 0.029 (3) | 0.018 (2) | 0.015 (2) | 0.0034 (18) | 0.0015 (17) |
C21E | 0.039 (2) | 0.050 (3) | 0.022 (2) | 0.019 (2) | −0.0003 (17) | 0.0085 (19) |
C22E | 0.060 (3) | 0.065 (3) | 0.033 (2) | 0.039 (3) | 0.012 (2) | 0.016 (2) |
O11E | 0.0452 (19) | 0.045 (2) | 0.0141 (14) | 0.0152 (16) | 0.0002 (12) | 0.0009 (13) |
O12E | 0.0425 (18) | 0.0409 (19) | 0.0223 (15) | 0.0089 (15) | 0.0056 (13) | 0.0069 (13) |
O21E | 0.0362 (16) | 0.048 (2) | 0.0227 (15) | 0.0193 (15) | 0.0023 (12) | 0.0069 (13) |
Geometric parameters (Å, º) top
C1A—C6A | 1.3930 | C12C—C13C | 1.468 (4) |
C1A—C2A | 1.4008 | C12C—H12C | 0.9500 |
C1A—C11A | 1.4821 | C13C—O12C | 1.230 (3) |
C2A—O21A | 1.3649 | C13C—O11C | 1.312 (3) |
C2A—C3A | 1.3788 | C21C—O21C | 1.437 (3) |
C3A—C4A | 1.3737 | C21C—C22C | 1.495 (3) |
C3A—H3A | 0.9500 | C21C—H21E | 0.9900 |
C4A—C5A | 1.3750 | C21C—H21F | 0.9900 |
C4A—H4A | 0.9500 | C22C—H22G | 0.9800 |
C5A—C6A | 1.3631 | C22C—H22H | 0.9800 |
C5A—H5A | 0.9500 | C22C—H22I | 0.9800 |
C6A—H6A | 0.9500 | O11C—H1C | 0.8400 |
C11A—C12A | 1.3389 | C1D—C6D | 1.391 (5) |
C11A—H11A | 0.9500 | C1D—C2D | 1.395 (5) |
C12A—C13A | 1.4585 | C1D—C11D | 1.495 (5) |
C12A—H12A | 0.9500 | C2D—O21D | 1.365 (4) |
C13A—O12A | 1.2635 | C2D—C3D | 1.399 (5) |
C13A—O11A | 1.2715 | C3D—C4D | 1.385 (5) |
C21A—O21A | 1.4363 | C3D—H3D | 0.9500 |
C21A—C22A | 1.4941 | C4D—C5D | 1.375 (6) |
C21A—H21A | 0.9900 | C4D—H4D | 0.9500 |
C21A—H21B | 0.9900 | C5D—C6D | 1.387 (6) |
C22A—H22A | 0.9800 | C5D—H5D | 0.9500 |
C22A—H22B | 0.9800 | C6D—H6D | 0.9500 |
C22A—H22C | 0.9800 | C11D—C12D | 1.539 (5) |
O11A—H1A | 0.8400 | C11D—C12E | 1.645 (7) |
C1B—C6B | 1.3842 | C11D—H11D | 1.0000 |
C1B—C2B | 1.4043 | C12D—C13D | 1.527 (6) |
C1B—C11B | 1.4677 | C12D—C11E | 1.635 (6) |
C2B—O21B | 1.3643 | C12D—H12D | 1.0000 |
C2B—C3B | 1.3827 | C13D—O12D | 1.210 (4) |
C3B—C4B | 1.3764 | C13D—O11D | 1.322 (4) |
C3B—H3B | 0.9500 | C21D—O21D | 1.424 (4) |
C4B—C5B | 1.3784 | C21D—C22D | 1.504 (5) |
C4B—H4B | 0.9500 | C21D—H21G | 0.9900 |
C5B—C6B | 1.3773 | C21D—H21H | 0.9900 |
C5B—H5B | 0.9500 | C22D—H22J | 0.9800 |
C6B—H6B | 0.9500 | C22D—H22K | 0.9800 |
C11B—C12B | 1.3405 | C22D—H22L | 0.9800 |
C11B—H11B | 0.9500 | O11D—H1D | 0.8400 |
C12B—C13B | 1.4590 | C1E—C6E | 1.386 (5) |
C12B—H12B | 0.9500 | C1E—C2E | 1.387 (5) |
C13B—O12B | 1.2632 | C1E—C11E | 1.507 (6) |
C13B—O11B | 1.2894 | C2E—O21E | 1.379 (4) |
C21B—O21B | 1.4331 | C2E—C3E | 1.393 (5) |
C21B—C22B | 1.4962 | C3E—C4E | 1.388 (5) |
C21B—H21C | 0.9900 | C3E—H3E | 0.9500 |
C21B—H21D | 0.9900 | C4E—C5E | 1.375 (6) |
C22B—H22D | 0.9800 | C4E—H4E | 0.9500 |
C22B—H22E | 0.9800 | C5E—C6E | 1.385 (6) |
C22B—H22F | 0.9800 | C5E—H5E | 0.9500 |
O11B—H1B | 0.8400 | C6E—H6E | 0.9500 |
C1C—C6C | 1.397 (3) | C11E—C12E | 1.540 (5) |
C1C—C2C | 1.402 (3) | C11E—H11E | 1.0000 |
C1C—C11C | 1.457 (4) | C12E—C13E | 1.511 (5) |
C2C—O21C | 1.365 (3) | C12E—H12E | 1.0000 |
C2C—C3C | 1.392 (4) | C13E—O12E | 1.219 (4) |
C3C—C4C | 1.378 (4) | C13E—O11E | 1.306 (4) |
C3C—H3C | 0.9500 | C21E—O21E | 1.434 (4) |
C4C—C5C | 1.378 (4) | C21E—C22E | 1.504 (5) |
C4C—H4C | 0.9500 | C21E—H21I | 0.9900 |
C5C—C6C | 1.381 (4) | C21E—H21J | 0.9900 |
C5C—H5C | 0.9500 | C22E—H22M | 0.9800 |
C6C—H6C | 0.9500 | C22E—H22N | 0.9800 |
C11C—C12C | 1.336 (3) | C22E—H22O | 0.9800 |
C11C—H11C | 0.9500 | O11E—H1E | 0.8400 |
| | | |
C6A—C1A—C2A | 117.9 | C11C—C12C—C13C | 121.8 (3) |
C6A—C1A—C11A | 121.2 | C11C—C12C—H12C | 119.1 |
C2A—C1A—C11A | 120.9 | C13C—C12C—H12C | 119.1 |
O21A—C2A—C3A | 123.6 | O12C—C13C—O11C | 123.4 (3) |
O21A—C2A—C1A | 116.0 | O12C—C13C—C12C | 123.6 (2) |
C3A—C2A—C1A | 120.4 | O11C—C13C—C12C | 113.1 (3) |
C4A—C3A—C2A | 119.9 | O21C—C21C—C22C | 107.2 (2) |
C4A—C3A—H3A | 120.1 | O21C—C21C—H21E | 110.3 |
C2A—C3A—H3A | 120.1 | C22C—C21C—H21E | 110.3 |
C3A—C4A—C5A | 120.7 | O21C—C21C—H21F | 110.3 |
C3A—C4A—H4A | 119.7 | C22C—C21C—H21F | 110.3 |
C5A—C4A—H4A | 119.7 | H21E—C21C—H21F | 108.5 |
C6A—C5A—C4A | 119.6 | C21C—C22C—H22G | 109.5 |
C6A—C5A—H5A | 120.2 | C21C—C22C—H22H | 109.5 |
C4A—C5A—H5A | 120.2 | H22G—C22C—H22H | 109.5 |
C5A—C6A—C1A | 121.6 | C21C—C22C—H22I | 109.5 |
C5A—C6A—H6A | 119.2 | H22G—C22C—H22I | 109.5 |
C1A—C6A—H6A | 119.2 | H22H—C22C—H22I | 109.5 |
C12A—C11A—C1A | 128.2 | C13C—O11C—H1C | 109.5 |
C12A—C11A—H11A | 115.9 | C2C—O21C—C21C | 118.20 (19) |
C1A—C11A—H11A | 115.9 | C6D—C1D—C2D | 117.9 (4) |
C11A—C12A—C13A | 122.7 | C6D—C1D—C11D | 124.5 (4) |
C11A—C12A—H12A | 118.7 | C2D—C1D—C11D | 117.0 (3) |
C13A—C12A—H12A | 118.7 | O21D—C2D—C1D | 115.1 (3) |
O12A—C13A—O11A | 124.5 | O21D—C2D—C3D | 123.8 (3) |
O12A—C13A—C12A | 117.5 | C1D—C2D—C3D | 121.1 (4) |
O11A—C13A—C12A | 118.0 | C4D—C3D—C2D | 118.9 (4) |
O21A—C21A—C22A | 107.2 | C4D—C3D—H3D | 120.5 |
O21A—C21A—H21A | 110.3 | C2D—C3D—H3D | 120.5 |
C22A—C21A—H21A | 110.3 | C5D—C4D—C3D | 121.3 (4) |
O21A—C21A—H21B | 110.3 | C5D—C4D—H4D | 119.4 |
C22A—C21A—H21B | 110.3 | C3D—C4D—H4D | 119.4 |
H21A—C21A—H21B | 108.5 | C4D—C5D—C6D | 119.1 (4) |
C21A—C22A—H22A | 109.5 | C4D—C5D—H5D | 120.5 |
C21A—C22A—H22B | 109.5 | C6D—C5D—H5D | 120.5 |
H22A—C22A—H22B | 109.5 | C5D—C6D—C1D | 121.8 (4) |
C21A—C22A—H22C | 109.5 | C5D—C6D—H6D | 119.1 |
H22A—C22A—H22C | 109.5 | C1D—C6D—H6D | 119.1 |
H22B—C22A—H22C | 109.5 | C1D—C11D—C12D | 119.4 (3) |
C13A—O11A—H1A | 109.5 | C1D—C11D—C12E | 116.7 (4) |
C2A—O21A—C21A | 118.8 | C12D—C11D—C12E | 90.0 (3) |
C6B—C1B—C2B | 118.0 | C1D—C11D—H11D | 109.8 |
C6B—C1B—C11B | 120.8 | C12D—C11D—H11D | 109.8 |
C2B—C1B—C11B | 121.2 | C12E—C11D—H11D | 109.8 |
O21B—C2B—C3B | 123.3 | C13D—C12D—C11D | 115.2 (3) |
O21B—C2B—C1B | 116.1 | C13D—C12D—C11E | 112.3 (3) |
C3B—C2B—C1B | 120.6 | C11D—C12D—C11E | 90.1 (3) |
C4B—C3B—C2B | 119.6 | C13D—C12D—H12D | 112.5 |
C4B—C3B—H3B | 120.2 | C11D—C12D—H12D | 112.5 |
C2B—C3B—H3B | 120.2 | C11E—C12D—H12D | 112.5 |
C3B—C4B—C5B | 120.9 | O12D—C13D—O11D | 122.6 (4) |
C3B—C4B—H4B | 119.6 | O12D—C13D—C12D | 123.2 (4) |
C5B—C4B—H4B | 119.6 | O11D—C13D—C12D | 113.6 (3) |
C6B—C5B—C4B | 119.2 | O21D—C21D—C22D | 107.8 (3) |
C6B—C5B—H5B | 120.4 | O21D—C21D—H21G | 110.1 |
C4B—C5B—H5B | 120.4 | C22D—C21D—H21G | 110.1 |
C5B—C6B—C1B | 121.7 | O21D—C21D—H21H | 110.1 |
C5B—C6B—H6B | 119.1 | C22D—C21D—H21H | 110.1 |
C1B—C6B—H6B | 119.1 | H21G—C21D—H21H | 108.5 |
C12B—C11B—C1B | 127.4 | C13D—O11D—H1D | 109.5 |
C12B—C11B—H11B | 116.3 | C2D—O21D—C21D | 118.2 (3) |
C1B—C11B—H11B | 116.3 | C6E—C1E—C2E | 118.6 (4) |
C11B—C12B—C13B | 122.5 | C6E—C1E—C11E | 124.3 (4) |
C11B—C12B—H12B | 118.7 | C2E—C1E—C11E | 116.2 (4) |
C13B—C12B—H12B | 118.7 | O21E—C2E—C1E | 115.1 (3) |
O12B—C13B—O11B | 124.4 | O21E—C2E—C3E | 123.9 (3) |
O12B—C13B—C12B | 120.1 | C1E—C2E—C3E | 121.0 (4) |
O11B—C13B—C12B | 115.4 | C4E—C3E—C2E | 118.8 (4) |
O21B—C21B—C22B | 107.2 | C4E—C3E—H3E | 120.6 |
O21B—C21B—H21C | 110.3 | C2E—C3E—H3E | 120.6 |
C22B—C21B—H21C | 110.3 | C5E—C4E—C3E | 121.0 (4) |
O21B—C21B—H21D | 110.3 | C5E—C4E—H4E | 119.5 |
C22B—C21B—H21D | 110.3 | C3E—C4E—H4E | 119.5 |
H21C—C21B—H21D | 108.5 | C4E—C5E—C6E | 119.3 (4) |
C21B—C22B—H22D | 109.5 | C4E—C5E—H5E | 120.3 |
C21B—C22B—H22E | 109.5 | C6E—C5E—H5E | 120.3 |
H22D—C22B—H22E | 109.5 | C5E—C6E—C1E | 121.2 (4) |
C21B—C22B—H22F | 109.5 | C5E—C6E—H6E | 119.4 |
H22D—C22B—H22F | 109.5 | C1E—C6E—H6E | 119.4 |
H22E—C22B—H22F | 109.5 | C1E—C11E—C12E | 119.7 (4) |
C13B—O11B—H1B | 109.5 | C1E—C11E—C12D | 116.4 (4) |
C2B—O21B—C21B | 118.3 | C12E—C11E—C12D | 90.3 (3) |
C6C—C1C—C2C | 117.7 (3) | C1E—C11E—H11E | 109.7 |
C6C—C1C—C11C | 122.3 (2) | C12E—C11E—H11E | 109.7 |
C2C—C1C—C11C | 120.0 (2) | C12D—C11E—H11E | 109.7 |
O21C—C2C—C3C | 123.2 (2) | C13E—C12E—C11E | 115.9 (4) |
O21C—C2C—C1C | 116.4 (2) | C13E—C12E—C11D | 111.5 (3) |
C3C—C2C—C1C | 120.5 (3) | C11E—C12E—C11D | 89.7 (3) |
C4C—C3C—C2C | 119.7 (3) | C13E—C12E—H12E | 112.6 |
C4C—C3C—H3C | 120.1 | C11E—C12E—H12E | 112.6 |
C2C—C3C—H3C | 120.1 | C11D—C12E—H12E | 112.6 |
C5C—C4C—C3C | 121.1 (3) | O12E—C13E—O11E | 124.3 (4) |
C5C—C4C—H4C | 119.4 | O12E—C13E—C12E | 122.4 (3) |
C3C—C4C—H4C | 119.4 | O11E—C13E—C12E | 112.6 (3) |
C4C—C5C—C6C | 118.9 (3) | O21E—C21E—C22E | 107.5 (3) |
C4C—C5C—H5C | 120.5 | O21E—C21E—H21I | 110.2 |
C6C—C5C—H5C | 120.5 | C22E—C21E—H21I | 110.2 |
C5C—C6C—C1C | 122.0 (3) | O21E—C21E—H21J | 110.2 |
C5C—C6C—H6C | 119.0 | C22E—C21E—H21J | 110.2 |
C1C—C6C—H6C | 119.0 | H21I—C21E—H21J | 108.5 |
C12C—C11C—C1C | 126.0 (3) | C13E—O11E—H1E | 109.5 |
C12C—C11C—H11C | 117.0 | C2E—O21E—C21E | 117.7 (3) |
C1C—C11C—H11C | 117.0 | | |
| | | |
C6A—C1A—C2A—O21A | −179.8 | C6D—C1D—C2D—C3D | −0.2 (6) |
C11A—C1A—C2A—O21A | −3.3 | C11D—C1D—C2D—C3D | −171.2 (4) |
C6A—C1A—C2A—C3A | 1.6 | O21D—C2D—C3D—C4D | 179.6 (4) |
C11A—C1A—C2A—C3A | 178.1 | C1D—C2D—C3D—C4D | 0.1 (6) |
O21A—C2A—C3A—C4A | 179.9 | C2D—C3D—C4D—C5D | −0.7 (6) |
C1A—C2A—C3A—C4A | −1.6 | C3D—C4D—C5D—C6D | 1.5 (7) |
C2A—C3A—C4A—C5A | 0.6 | C4D—C5D—C6D—C1D | −1.6 (7) |
C3A—C4A—C5A—C6A | 0.3 | C2D—C1D—C6D—C5D | 1.0 (6) |
C4A—C5A—C6A—C1A | −0.2 | C11D—C1D—C6D—C5D | 171.3 (5) |
C2A—C1A—C6A—C5A | −0.7 | C6D—C1D—C11D—C12D | 14.0 (6) |
C11A—C1A—C6A—C5A | −177.2 | C2D—C1D—C11D—C12D | −175.6 (4) |
C6A—C1A—C11A—C12A | 0.1 | C6D—C1D—C11D—C12E | −92.3 (5) |
C2A—C1A—C11A—C12A | −176.3 | C2D—C1D—C11D—C12E | 78.0 (5) |
C1A—C11A—C12A—C13A | −179.9 | C1D—C11D—C12D—C13D | 125.0 (4) |
C11A—C12A—C13A—O12A | −0.5 | C12E—C11D—C12D—C13D | −114.0 (4) |
C11A—C12A—C13A—O11A | 179.6 | C1D—C11D—C12D—C11E | −120.2 (4) |
C3A—C2A—O21A—C21A | 1.1 | C12E—C11D—C12D—C11E | 0.8 (3) |
C1A—C2A—O21A—C21A | −177.4 | C11D—C12D—C13D—O12D | 31.2 (6) |
C22A—C21A—O21A—C2A | 175.5 | C11E—C12D—C13D—O12D | −70.1 (5) |
C6B—C1B—C2B—O21B | 179.7 | C11D—C12D—C13D—O11D | −158.0 (3) |
C11B—C1B—C2B—O21B | 2.6 | C11E—C12D—C13D—O11D | 100.8 (4) |
C6B—C1B—C2B—C3B | 0.1 | C1D—C2D—O21D—C21D | −169.0 (4) |
C11B—C1B—C2B—C3B | −177.0 | C3D—C2D—O21D—C21D | 11.4 (6) |
O21B—C2B—C3B—C4B | −179.6 | C22D—C21D—O21D—C2D | 174.4 (3) |
C1B—C2B—C3B—C4B | −0.1 | C6E—C1E—C2E—O21E | 179.0 (3) |
C2B—C3B—C4B—C5B | −0.2 | C11E—C1E—C2E—O21E | −11.2 (5) |
C3B—C4B—C5B—C6B | 0.3 | C6E—C1E—C2E—C3E | −0.6 (6) |
C4B—C5B—C6B—C1B | −0.3 | C11E—C1E—C2E—C3E | 169.2 (4) |
C2B—C1B—C6B—C5B | 0.1 | O21E—C2E—C3E—C4E | −178.3 (4) |
C11B—C1B—C6B—C5B | 177.2 | C1E—C2E—C3E—C4E | 1.3 (7) |
C6B—C1B—C11B—C12B | 8.9 | C2E—C3E—C4E—C5E | −0.6 (7) |
C2B—C1B—C11B—C12B | −174.1 | C3E—C4E—C5E—C6E | −0.6 (7) |
C1B—C11B—C12B—C13B | 179.5 | C4E—C5E—C6E—C1E | 1.3 (7) |
C11B—C12B—C13B—O12B | 6.2 | C2E—C1E—C6E—C5E | −0.7 (6) |
C11B—C12B—C13B—O11B | −173.4 | C11E—C1E—C6E—C5E | −169.6 (5) |
C3B—C2B—O21B—C21B | −3.4 | C6E—C1E—C11E—C12E | −7.9 (6) |
C1B—C2B—O21B—C21B | 177.0 | C2E—C1E—C11E—C12E | −177.0 (4) |
C22B—C21B—O21B—C2B | −175.8 | C6E—C1E—C11E—C12D | 98.9 (5) |
C6C—C1C—C2C—O21C | 177.4 (3) | C2E—C1E—C11E—C12D | −70.2 (5) |
C11C—C1C—C2C—O21C | −4.1 (4) | C13D—C12D—C11E—C1E | −7.2 (5) |
C6C—C1C—C2C—C3C | −3.2 (5) | C11D—C12D—C11E—C1E | −124.6 (4) |
C11C—C1C—C2C—C3C | 175.3 (3) | C13D—C12D—C11E—C12E | 116.6 (3) |
O21C—C2C—C3C—C4C | −178.5 (3) | C11D—C12D—C11E—C12E | −0.9 (3) |
C1C—C2C—C3C—C4C | 2.2 (5) | C1E—C11E—C12E—C13E | −124.4 (4) |
C2C—C3C—C4C—C5C | 0.0 (6) | C12D—C11E—C12E—C13E | 114.7 (4) |
C3C—C4C—C5C—C6C | −1.1 (6) | C1E—C11E—C12E—C11D | 121.8 (4) |
C4C—C5C—C6C—C1C | 0.0 (5) | C12D—C11E—C12E—C11D | 0.8 (3) |
C2C—C1C—C6C—C5C | 2.1 (5) | C1D—C11D—C12E—C13E | 4.6 (5) |
C11C—C1C—C6C—C5C | −176.3 (3) | C12D—C11D—C12E—C13E | −118.7 (3) |
C6C—C1C—C11C—C12C | 3.1 (5) | C1D—C11D—C12E—C11E | 122.4 (4) |
C2C—C1C—C11C—C12C | −175.3 (3) | C12D—C11D—C12E—C11E | −0.9 (3) |
C1C—C11C—C12C—C13C | 176.3 (3) | C11E—C12E—C13E—O12E | −22.7 (6) |
C11C—C12C—C13C—O12C | 6.0 (5) | C11D—C12E—C13E—O12E | 77.9 (5) |
C11C—C12C—C13C—O11C | −173.4 (3) | C11E—C12E—C13E—O11E | 166.4 (3) |
C3C—C2C—O21C—C21C | 3.5 (4) | C11D—C12E—C13E—O11E | −93.0 (4) |
C1C—C2C—O21C—C21C | −177.1 (2) | C1E—C2E—O21E—C21E | 165.6 (3) |
C22C—C21C—O21C—C2C | −179.6 (2) | C3E—C2E—O21E—C21E | −14.8 (5) |
C6D—C1D—C2D—O21D | −179.8 (3) | C22E—C21E—O21E—C2E | −171.6 (3) |
C11D—C1D—C2D—O21D | 9.2 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11A—H1A···O12Ai | 0.84 | 1.63 | 2.429 (8) | 158 |
O11B—H1B···O12Cii | 0.84 | 1.70 | 2.522 (5) | 167 |
O11C—H1C···O12Bii | 0.84 | 1.77 | 2.603 (5) | 171 |
O11E—H1E···O12Cii | 0.84 | 1.87 | 2.686 (3) | 164 |
O11C—H1C···O12Eii | 0.84 | 1.85 | 2.685 (4) | 171 |
O11D—H1D···O12Di | 0.84 | 2.05 | 2.798 (5) | 148 |
O11D—H1D···O12Ai | 0.84 | 2.02 | 2.727 (5) | 141 |
O11A—H1A···O12Di | 0.84 | 1.63 | 2.453 (4) | 164 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z+1. |
(rd36hlts) (
E)-3-(2-Ethoxyphenyl)propenoic acid and
trans-2,4-bis(2-ethoxyphenyl)-
trans-1,3-cyclobutane-dicarboxylic acid
top
Crystal data top
0.912(C22H24O6)·1.176(C11H12O3) | Z = 2 |
Mr = 576.62 | F(000) = 612 |
Triclinic, P1 | Dx = 1.301 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3863 (13) Å | Cell parameters from 1002 reflections |
b = 10.9711 (18) Å | θ = 2.6–27.0° |
c = 17.427 (3) Å | µ = 0.09 mm−1 |
α = 98.323 (3)° | T = 173 K |
β = 91.809 (3)° | Irregular, white |
γ = 111.336 (3)° | 0.45 × 0.24 × 0.14 mm |
V = 1471.6 (4) Å3 | |
Data collection top
CCD area detector diffractometer | 3015 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 25.5°, θmin = 1.2° |
phi and ω scans | h = −10→10 |
8385 measured reflections | k = −13→7 |
5439 independent reflections | l = −21→19 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0627P)2] where P = (Fo2 + 2Fc2)/3 |
5439 reflections | (Δ/σ)max < 0.001 |
395 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Crystal data top
0.912(C22H24O6)·1.176(C11H12O3) | γ = 111.336 (3)° |
Mr = 576.62 | V = 1471.6 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.3863 (13) Å | Mo Kα radiation |
b = 10.9711 (18) Å | µ = 0.09 mm−1 |
c = 17.427 (3) Å | T = 173 K |
α = 98.323 (3)° | 0.45 × 0.24 × 0.14 mm |
β = 91.809 (3)° | |
Data collection top
CCD area detector diffractometer | 3015 reflections with I > 2σ(I) |
8385 measured reflections | Rint = 0.028 |
5439 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.140 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.19 e Å−3 |
5439 reflections | Δρmin = −0.26 e Å−3 |
395 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 | Occ. (<1) |
C1A | 1.0137 (14) | 0.0190 (11) | 0.2217 (7) | 0.045 (3)* | 0.088 (3) |
C2A | 1.0055 (14) | 0.0165 (11) | 0.3016 (7) | 0.045 (3)* | 0.088 (3) |
C3A | 1.1474 (14) | 0.0252 (11) | 0.3475 (7) | 0.045 (3)* | 0.088 (3) |
H3A | 1.1421 | 0.0257 | 0.4019 | 0.054* | 0.088 (3) |
C4A | 1.2966 (14) | 0.0331 (11) | 0.3144 (7) | 0.045 (3)* | 0.088 (3) |
H4A | 1.3939 | 0.0383 | 0.3461 | 0.054* | 0.088 (3) |
C5A | 1.3067 (14) | 0.0338 (11) | 0.2359 (7) | 0.045 (3)* | 0.088 (3) |
H5A | 1.4102 | 0.0388 | 0.2134 | 0.054* | 0.088 (3) |
C6A | 1.1674 (14) | 0.0270 (11) | 0.1905 (7) | 0.045 (3)* | 0.088 (3) |
H6A | 1.1753 | 0.0278 | 0.1363 | 0.054* | 0.088 (3) |
C11A | 0.8605 (14) | 0.0056 (11) | 0.1713 (7) | 0.024 (6)* | 0.088 (3) |
H11A | 0.7609 | 0.0010 | 0.1972 | 0.029* | 0.088 (3) |
C12A | 0.8448 (14) | −0.0007 (11) | 0.0940 (7) | 0.016 (5)* | 0.088 (3) |
H12A | 0.9414 | 0.0034 | 0.0659 | 0.019* | 0.088 (3) |
C13A | 0.6856 (14) | −0.0137 (11) | 0.0512 (7) | 0.045 (3)* | 0.088 (3) |
C21A | 0.8378 (14) | 0.0107 (11) | 0.4119 (7) | 0.045 (3)* | 0.088 (3) |
H21A | 0.9281 | 0.0912 | 0.4418 | 0.054* | 0.088 (3) |
H21B | 0.8511 | −0.0683 | 0.4278 | 0.054* | 0.088 (3) |
C22A | 0.6637 (14) | 0.0114 (11) | 0.4270 (7) | 0.045 (3)* | 0.088 (3) |
H22A | 0.6491 | 0.0131 | 0.4826 | 0.068* | 0.088 (3) |
H22B | 0.5755 | −0.0687 | 0.3971 | 0.068* | 0.088 (3) |
H22C | 0.6522 | 0.0901 | 0.4111 | 0.068* | 0.088 (3) |
O11A | 0.6837 (14) | −0.0182 (11) | −0.0221 (7) | 0.045 (3)* | 0.088 (3) |
H1A | 0.5860 | −0.0257 | −0.0403 | 0.068* | 0.088 (3) |
O12A | 0.5587 (14) | −0.0199 (11) | 0.0899 (7) | 0.045 (3)* | 0.088 (3) |
O21A | 0.8525 (14) | 0.0081 (11) | 0.3298 (7) | 0.045 (3)* | 0.088 (3) |
C1B | 0.7657 (16) | 0.3289 (12) | 0.1256 (7) | 0.045 (3)* | 0.088 (3) |
C2B | 0.7669 (16) | 0.3147 (12) | 0.0443 (7) | 0.045 (3)* | 0.088 (3) |
C3B | 0.6277 (16) | 0.3116 (12) | −0.0017 (7) | 0.045 (3)* | 0.088 (3) |
H3B | 0.6293 | 0.3020 | −0.0567 | 0.054* | 0.088 (3) |
C4B | 0.4867 (16) | 0.3223 (12) | 0.0326 (7) | 0.045 (3)* | 0.088 (3) |
H4B | 0.3912 | 0.3204 | 0.0009 | 0.054* | 0.088 (3) |
C5B | 0.4822 (16) | 0.3359 (12) | 0.1122 (7) | 0.045 (3)* | 0.088 (3) |
H5B | 0.3842 | 0.3428 | 0.1355 | 0.054* | 0.088 (3) |
C6B | 0.6215 (16) | 0.3394 (12) | 0.1578 (7) | 0.045 (3)* | 0.088 (3) |
H6B | 0.6185 | 0.3492 | 0.2128 | 0.054* | 0.088 (3) |
C11B | 0.9158 (16) | 0.3389 (12) | 0.1755 (7) | 0.016 (6)* | 0.088 (3) |
H11B | 1.0162 | 0.3438 | 0.1502 | 0.020* | 0.088 (3) |
C12B | 0.9274 (16) | 0.3418 (12) | 0.2527 (7) | 0.013 (5)* | 0.088 (3) |
H12B | 0.8300 | 0.3378 | 0.2801 | 0.016* | 0.088 (3) |
C13B | 1.0839 (16) | 0.3509 (12) | 0.2962 (7) | 0.045 (3)* | 0.088 (3) |
C21B | 0.9159 (16) | 0.2843 (12) | −0.0679 (7) | 0.045 (3)* | 0.088 (3) |
H21C | 0.9092 | 0.3611 | −0.0895 | 0.054* | 0.088 (3) |
H21D | 0.8174 | 0.2037 | −0.0922 | 0.054* | 0.088 (3) |
C22B | 1.0817 (16) | 0.2678 (12) | −0.0842 (7) | 0.045 (3)* | 0.088 (3) |
H22D | 1.0889 | 0.2531 | −0.1406 | 0.068* | 0.088 (3) |
H22E | 1.0867 | 0.1915 | −0.0626 | 0.068* | 0.088 (3) |
H22F | 1.1781 | 0.3482 | −0.0600 | 0.068* | 0.088 (3) |
O11B | 1.0706 (16) | 0.3395 (12) | 0.3686 (7) | 0.045 (3)* | 0.088 (3) |
H1B | 1.1657 | 0.3458 | 0.3893 | 0.068* | 0.088 (3) |
O12B | 1.2199 (16) | 0.3680 (12) | 0.2627 (7) | 0.045 (3)* | 0.088 (3) |
O21B | 0.9117 (16) | 0.3054 (12) | 0.0150 (7) | 0.045 (3)* | 0.088 (3) |
C1C | 0.2223 (3) | 0.6536 (2) | 0.42299 (12) | 0.0314 (6) | |
C2C | 0.2244 (3) | 0.6470 (2) | 0.34199 (13) | 0.0348 (6) | |
C3C | 0.0739 (3) | 0.6236 (3) | 0.29572 (14) | 0.0488 (7) | |
H3C | 0.0745 | 0.6144 | 0.2407 | 0.059* | |
C4C | −0.0752 (3) | 0.6137 (3) | 0.32968 (15) | 0.0555 (8) | |
H4C | −0.1771 | 0.5974 | 0.2978 | 0.067* | |
C5C | −0.0786 (3) | 0.6272 (3) | 0.40957 (15) | 0.0486 (7) | |
H5C | −0.1808 | 0.6237 | 0.4328 | 0.058* | |
C6C | 0.0689 (3) | 0.6460 (2) | 0.45519 (14) | 0.0381 (6) | |
H6C | 0.0660 | 0.6540 | 0.5101 | 0.046* | |
C11C | 0.3734 (3) | 0.6618 (2) | 0.47051 (12) | 0.0312 (6) | |
H11C | 0.4741 | 0.6704 | 0.4447 | 0.037* | |
C12C | 0.3839 (3) | 0.6584 (2) | 0.54665 (13) | 0.0370 (6) | |
H12C | 0.2887 | 0.6575 | 0.5750 | 0.044* | |
C13C | 0.5366 (3) | 0.6559 (2) | 0.58789 (13) | 0.0358 (6) | |
C21C | 0.3890 (3) | 0.6673 (3) | 0.23126 (12) | 0.0404 (6) | |
H21E | 0.3547 | 0.7393 | 0.2174 | 0.048* | |
H21F | 0.3113 | 0.5821 | 0.2002 | 0.048* | |
C22C | 0.5712 (3) | 0.6925 (3) | 0.21517 (13) | 0.0469 (7) | |
H22G | 0.6478 | 0.7722 | 0.2501 | 0.070* | |
H22H | 0.5857 | 0.7057 | 0.1610 | 0.070* | |
H22I | 0.5997 | 0.6162 | 0.2238 | 0.070* | |
O11C | 0.51355 (19) | 0.63430 (18) | 0.65987 (9) | 0.0530 (5) | |
H1C | 0.6043 | 0.6331 | 0.6810 | 0.080* | |
O12C | 0.6715 (2) | 0.66913 (17) | 0.55821 (8) | 0.0439 (5) | |
O21C | 0.37849 (18) | 0.66266 (17) | 0.31313 (8) | 0.0388 (4) | |
C1D | 1.0117 (3) | 0.0381 (2) | 0.23083 (14) | 0.0290 (6) | 0.912 (3) |
C2D | 0.9942 (3) | −0.0037 (3) | 0.30312 (14) | 0.0298 (6) | 0.912 (3) |
C3D | 1.1228 (3) | −0.0346 (3) | 0.33792 (15) | 0.0412 (8) | 0.912 (3) |
H3D | 1.1105 | −0.0624 | 0.3873 | 0.049* | 0.912 (3) |
C4D | 1.2683 (3) | −0.0248 (3) | 0.30058 (16) | 0.0447 (8) | 0.912 (3) |
H4D | 1.3560 | −0.0461 | 0.3244 | 0.054* | 0.912 (3) |
C5D | 1.2880 (4) | 0.0155 (3) | 0.22913 (16) | 0.0413 (7) | 0.912 (3) |
H5D | 1.3884 | 0.0216 | 0.2036 | 0.050* | 0.912 (3) |
C6D | 1.1600 (3) | 0.0472 (3) | 0.19473 (15) | 0.0351 (7) | 0.912 (3) |
H6D | 1.1740 | 0.0757 | 0.1456 | 0.042* | 0.912 (3) |
C11D | 0.8753 (3) | 0.0841 (3) | 0.20037 (13) | 0.0319 (6) | 0.912 (3) |
H11D | 0.7585 | 0.0210 | 0.2082 | 0.038* | 0.912 (3) |
C12D | 0.8773 (3) | 0.1158 (2) | 0.11698 (13) | 0.0325 (7) | 0.912 (3) |
H12D | 0.9794 | 0.1099 | 0.0910 | 0.039* | 0.912 (3) |
C13D | 0.7111 (3) | 0.0426 (3) | 0.06600 (13) | 0.0293 (6) | 0.912 (3) |
C21D | 0.8345 (3) | −0.0253 (3) | 0.41589 (14) | 0.0417 (7) | 0.912 (3) |
H21G | 0.9332 | 0.0447 | 0.4485 | 0.050* | 0.912 (3) |
H21H | 0.8368 | −0.1128 | 0.4225 | 0.050* | 0.912 (3) |
C22D | 0.6696 (3) | −0.0150 (3) | 0.43987 (15) | 0.0428 (7) | 0.912 (3) |
H22J | 0.6697 | 0.0726 | 0.4342 | 0.064* | 0.912 (3) |
H22K | 0.6581 | −0.0270 | 0.4943 | 0.064* | 0.912 (3) |
H22L | 0.5729 | −0.0840 | 0.4068 | 0.064* | 0.912 (3) |
O11D | 0.7303 (2) | 0.0347 (2) | −0.00935 (9) | 0.0390 (5) | 0.912 (3) |
H1D | 0.6353 | −0.0109 | −0.0348 | 0.059* | 0.912 (3) |
O12D | 0.5711 (2) | 0.0068 (2) | 0.09141 (10) | 0.0362 (5) | 0.912 (3) |
O21D | 0.8454 (2) | −0.0097 (2) | 0.33606 (10) | 0.0333 (5) | 0.912 (3) |
C1E | 0.7681 (3) | 0.3129 (3) | 0.11991 (14) | 0.0305 (6) | 0.912 (3) |
C2E | 0.7770 (3) | 0.3377 (3) | 0.04359 (14) | 0.0303 (6) | 0.912 (3) |
C3E | 0.6464 (3) | 0.3634 (3) | 0.00652 (15) | 0.0420 (8) | 0.912 (3) |
H3E | 0.6529 | 0.3794 | −0.0457 | 0.050* | 0.912 (3) |
C4E | 0.5075 (3) | 0.3656 (3) | 0.04598 (17) | 0.0452 (8) | 0.912 (3) |
H4E | 0.4169 | 0.3810 | 0.0202 | 0.054* | 0.912 (3) |
C5E | 0.4977 (4) | 0.3459 (3) | 0.12222 (17) | 0.0419 (7) | 0.912 (3) |
H5E | 0.4033 | 0.3504 | 0.1496 | 0.050* | 0.912 (3) |
C6E | 0.6289 (3) | 0.3192 (3) | 0.15836 (16) | 0.0381 (7) | 0.912 (3) |
H6E | 0.6227 | 0.3050 | 0.2108 | 0.046* | 0.912 (3) |
C11E | 0.9009 (3) | 0.2651 (3) | 0.15133 (13) | 0.0316 (6) | 0.912 (3) |
H11E | 1.0189 | 0.3268 | 0.1440 | 0.038* | 0.912 (3) |
C12E | 0.8958 (3) | 0.2327 (3) | 0.23490 (13) | 0.0321 (7) | 0.912 (3) |
H12E | 0.7922 | 0.2374 | 0.2601 | 0.038* | 0.912 (3) |
C13E | 1.0594 (3) | 0.3035 (3) | 0.28721 (14) | 0.0290 (6) | 0.912 (3) |
C21E | 0.9162 (3) | 0.3193 (3) | −0.07374 (14) | 0.0387 (7) | 0.912 (3) |
H21I | 0.9171 | 0.4017 | −0.0909 | 0.046* | 0.912 (3) |
H21J | 0.8102 | 0.2451 | −0.0979 | 0.046* | 0.912 (3) |
C22E | 1.0718 (4) | 0.2918 (3) | −0.09773 (16) | 0.0487 (8) | 0.912 (3) |
H22M | 1.1758 | 0.3689 | −0.0771 | 0.073* | 0.912 (3) |
H22N | 1.0670 | 0.2745 | −0.1547 | 0.073* | 0.912 (3) |
H22O | 1.0742 | 0.2140 | −0.0770 | 0.073* | 0.912 (3) |
O11E | 1.0387 (2) | 0.2971 (2) | 0.36085 (9) | 0.0364 (5) | 0.912 (3) |
H1E | 1.1353 | 0.3243 | 0.3863 | 0.055* | 0.912 (3) |
O12E | 1.1990 (3) | 0.3515 (2) | 0.26216 (11) | 0.0351 (5) | 0.912 (3) |
O21E | 0.9211 (2) | 0.3334 (2) | 0.00973 (10) | 0.0359 (5) | 0.912 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1C | 0.0349 (13) | 0.0308 (14) | 0.0286 (13) | 0.0123 (11) | 0.0033 (10) | 0.0049 (10) |
C2C | 0.0307 (13) | 0.0448 (16) | 0.0325 (14) | 0.0181 (12) | 0.0036 (11) | 0.0072 (11) |
C3C | 0.0418 (15) | 0.080 (2) | 0.0328 (15) | 0.0302 (15) | 0.0038 (12) | 0.0164 (14) |
C4C | 0.0403 (16) | 0.092 (2) | 0.0491 (17) | 0.0371 (16) | 0.0049 (13) | 0.0237 (16) |
C5C | 0.0381 (15) | 0.067 (2) | 0.0519 (17) | 0.0278 (15) | 0.0147 (13) | 0.0219 (15) |
C6C | 0.0404 (14) | 0.0432 (16) | 0.0347 (14) | 0.0196 (13) | 0.0062 (11) | 0.0081 (12) |
C11C | 0.0315 (13) | 0.0322 (14) | 0.0295 (13) | 0.0119 (11) | 0.0029 (10) | 0.0034 (10) |
C12C | 0.0347 (14) | 0.0459 (17) | 0.0295 (14) | 0.0146 (13) | 0.0021 (11) | 0.0047 (11) |
C13C | 0.0394 (15) | 0.0394 (16) | 0.0248 (13) | 0.0111 (13) | −0.0001 (11) | 0.0040 (11) |
C21C | 0.0427 (15) | 0.0586 (18) | 0.0255 (13) | 0.0239 (14) | 0.0046 (11) | 0.0106 (12) |
C22C | 0.0371 (14) | 0.0638 (19) | 0.0337 (14) | 0.0135 (14) | 0.0026 (11) | 0.0037 (13) |
O11C | 0.0392 (10) | 0.0894 (15) | 0.0296 (10) | 0.0196 (10) | 0.0003 (8) | 0.0199 (10) |
O12C | 0.0414 (10) | 0.0648 (13) | 0.0263 (9) | 0.0219 (9) | 0.0017 (8) | 0.0043 (8) |
O21C | 0.0320 (9) | 0.0614 (12) | 0.0269 (9) | 0.0207 (9) | 0.0016 (7) | 0.0110 (8) |
C1D | 0.0285 (14) | 0.0277 (15) | 0.0292 (14) | 0.0089 (12) | −0.0019 (11) | 0.0050 (11) |
C2D | 0.0310 (14) | 0.0288 (15) | 0.0287 (14) | 0.0105 (12) | −0.0018 (11) | 0.0046 (11) |
C3D | 0.0462 (17) | 0.052 (2) | 0.0322 (16) | 0.0262 (16) | −0.0050 (13) | 0.0106 (14) |
C4D | 0.0404 (17) | 0.054 (2) | 0.0488 (19) | 0.0305 (16) | −0.0042 (14) | 0.0044 (16) |
C5D | 0.0344 (16) | 0.054 (2) | 0.0397 (17) | 0.0236 (15) | 0.0002 (13) | 0.0012 (14) |
C6D | 0.0332 (15) | 0.0424 (18) | 0.0313 (15) | 0.0162 (14) | 0.0024 (12) | 0.0058 (13) |
C11D | 0.0295 (14) | 0.0384 (17) | 0.0291 (14) | 0.0134 (13) | 0.0002 (11) | 0.0087 (12) |
C12D | 0.0294 (14) | 0.0447 (18) | 0.0266 (14) | 0.0187 (13) | 0.0008 (11) | 0.0034 (12) |
C13D | 0.0367 (16) | 0.0339 (17) | 0.0215 (14) | 0.0171 (13) | 0.0038 (12) | 0.0063 (11) |
C21D | 0.0450 (17) | 0.057 (2) | 0.0286 (15) | 0.0236 (16) | −0.0003 (12) | 0.0124 (14) |
C22D | 0.0464 (17) | 0.056 (2) | 0.0307 (15) | 0.0239 (16) | 0.0031 (13) | 0.0105 (14) |
O11D | 0.0359 (11) | 0.0530 (14) | 0.0224 (10) | 0.0115 (11) | −0.0012 (8) | 0.0027 (9) |
O12D | 0.0335 (10) | 0.0431 (12) | 0.0272 (10) | 0.0090 (9) | 0.0006 (8) | 0.0055 (9) |
O21D | 0.0298 (10) | 0.0493 (12) | 0.0240 (10) | 0.0161 (9) | 0.0014 (7) | 0.0129 (8) |
C1E | 0.0302 (14) | 0.0327 (16) | 0.0301 (15) | 0.0134 (13) | −0.0007 (11) | 0.0065 (12) |
C2E | 0.0305 (14) | 0.0295 (16) | 0.0299 (14) | 0.0106 (12) | −0.0008 (11) | 0.0044 (12) |
C3E | 0.0453 (17) | 0.057 (2) | 0.0303 (15) | 0.0265 (16) | −0.0054 (13) | 0.0123 (14) |
C4E | 0.0423 (17) | 0.054 (2) | 0.0504 (19) | 0.0289 (16) | −0.0058 (14) | 0.0147 (16) |
C5E | 0.0372 (16) | 0.0492 (19) | 0.0469 (18) | 0.0244 (15) | 0.0029 (13) | 0.0099 (14) |
C6E | 0.0394 (16) | 0.0451 (19) | 0.0314 (15) | 0.0171 (14) | 0.0021 (12) | 0.0083 (13) |
C11E | 0.0293 (14) | 0.0382 (18) | 0.0257 (14) | 0.0110 (13) | 0.0001 (11) | 0.0051 (13) |
C12E | 0.0303 (14) | 0.0451 (18) | 0.0249 (14) | 0.0190 (13) | 0.0005 (11) | 0.0059 (12) |
C13E | 0.0390 (16) | 0.0316 (17) | 0.0208 (14) | 0.0193 (14) | 0.0009 (12) | 0.0020 (11) |
C21E | 0.0428 (16) | 0.053 (2) | 0.0236 (14) | 0.0205 (15) | 0.0011 (12) | 0.0091 (13) |
C22E | 0.0507 (18) | 0.063 (2) | 0.0347 (17) | 0.0243 (17) | 0.0055 (14) | 0.0075 (15) |
O11E | 0.0393 (11) | 0.0515 (13) | 0.0186 (9) | 0.0197 (10) | −0.0030 (8) | 0.0009 (9) |
O12E | 0.0356 (11) | 0.0392 (12) | 0.0268 (10) | 0.0106 (9) | −0.0013 (8) | 0.0044 (8) |
O21E | 0.0362 (10) | 0.0516 (13) | 0.0248 (10) | 0.0206 (10) | 0.0009 (8) | 0.0105 (9) |
Geometric parameters (Å, º) top
C1A—C6A | 1.3930 | C12C—C13C | 1.459 (3) |
C1A—C2A | 1.4008 | C12C—H12C | 0.9500 |
C1A—C11A | 1.4821 | C13C—O12C | 1.228 (2) |
C2A—O21A | 1.3649 | C13C—O11C | 1.317 (2) |
C2A—C3A | 1.3788 | C21C—O21C | 1.440 (2) |
C3A—C4A | 1.3737 | C21C—C22C | 1.495 (3) |
C3A—H3A | 0.9500 | C21C—H21E | 0.9900 |
C4A—C5A | 1.3750 | C21C—H21F | 0.9900 |
C4A—H4A | 0.9500 | C22C—H22G | 0.9800 |
C5A—C6A | 1.3631 | C22C—H22H | 0.9800 |
C5A—H5A | 0.9500 | C22C—H22I | 0.9800 |
C6A—H6A | 0.9500 | O11C—H1C | 0.8400 |
C11A—C12A | 1.3389 | C1D—C6D | 1.389 (3) |
C11A—H11A | 0.9500 | C1D—C2D | 1.396 (3) |
C12A—C13A | 1.4585 | C1D—C11D | 1.517 (3) |
C12A—H12A | 0.9500 | C2D—O21D | 1.374 (3) |
C13A—O12A | 1.2635 | C2D—C3D | 1.390 (3) |
C13A—O11A | 1.2715 | C3D—C4D | 1.378 (3) |
C21A—O21A | 1.4363 | C3D—H3D | 0.9500 |
C21A—C22A | 1.4941 | C4D—C5D | 1.376 (3) |
C21A—H21A | 0.9900 | C4D—H4D | 0.9500 |
C21A—H21B | 0.9900 | C5D—C6D | 1.387 (3) |
C22A—H22A | 0.9800 | C5D—H5D | 0.9500 |
C22A—H22B | 0.9800 | C6D—H6D | 0.9500 |
C22A—H22C | 0.9800 | C11D—C12D | 1.542 (3) |
O11A—H1A | 0.8400 | C11D—C12E | 1.599 (4) |
C1B—C6B | 1.3842 | C11D—H11D | 1.0000 |
C1B—C2B | 1.4043 | C12D—C13D | 1.509 (3) |
C1B—C11B | 1.4677 | C12D—C11E | 1.598 (4) |
C2B—O21B | 1.3643 | C12D—H12D | 1.0000 |
C2B—C3B | 1.3827 | C13D—O12D | 1.215 (3) |
C3B—C4B | 1.3764 | C13D—O11D | 1.322 (3) |
C3B—H3B | 0.9500 | C21D—O21D | 1.428 (3) |
C4B—C5B | 1.3784 | C21D—C22D | 1.496 (3) |
C4B—H4B | 0.9500 | C21D—H21G | 0.9900 |
C5B—C6B | 1.3773 | C21D—H21H | 0.9900 |
C5B—H5B | 0.9500 | C22D—H22J | 0.9800 |
C6B—H6B | 0.9500 | C22D—H22K | 0.9800 |
C11B—C12B | 1.3405 | C22D—H22L | 0.9800 |
C11B—H11B | 0.9500 | O11D—H1D | 0.8400 |
C12B—C13B | 1.4590 | C1E—C6E | 1.383 (3) |
C12B—H12B | 0.9500 | C1E—C2E | 1.395 (3) |
C13B—O12B | 1.2632 | C1E—C11E | 1.512 (3) |
C13B—O11B | 1.2893 | C2E—O21E | 1.374 (3) |
C21B—O21B | 1.4331 | C2E—C3E | 1.389 (3) |
C21B—C22B | 1.4961 | C3E—C4E | 1.377 (3) |
C21B—H21C | 0.9900 | C3E—H3E | 0.9500 |
C21B—H21D | 0.9900 | C4E—C5E | 1.377 (3) |
C22B—H22D | 0.9800 | C4E—H4E | 0.9500 |
C22B—H22E | 0.9800 | C5E—C6E | 1.392 (3) |
C22B—H22F | 0.9800 | C5E—H5E | 0.9500 |
O11B—H1B | 0.8400 | C6E—H6E | 0.9500 |
C1C—C6C | 1.399 (3) | C11E—C12E | 1.547 (3) |
C1C—C2C | 1.404 (3) | C11E—H11E | 1.0000 |
C1C—C11C | 1.459 (3) | C12E—C13E | 1.502 (3) |
C2C—O21C | 1.362 (2) | C12E—H12E | 1.0000 |
C2C—C3C | 1.396 (3) | C13E—O12E | 1.221 (3) |
C3C—C4C | 1.375 (3) | C13E—O11E | 1.309 (3) |
C3C—H3C | 0.9500 | C21E—O21E | 1.438 (3) |
C4C—C5C | 1.381 (3) | C21E—C22E | 1.501 (3) |
C4C—H4C | 0.9500 | C21E—H21I | 0.9900 |
C5C—C6C | 1.382 (3) | C21E—H21J | 0.9900 |
C5C—H5C | 0.9500 | C22E—H22M | 0.9800 |
C6C—H6C | 0.9500 | C22E—H22N | 0.9800 |
C11C—C12C | 1.334 (3) | C22E—H22O | 0.9800 |
C11C—H11C | 0.9500 | O11E—H1E | 0.8400 |
| | | |
C6A—C1A—C2A | 117.9 | C11C—C12C—C13C | 122.3 (2) |
C6A—C1A—C11A | 121.2 | C11C—C12C—H12C | 118.9 |
C2A—C1A—C11A | 120.9 | C13C—C12C—H12C | 118.9 |
O21A—C2A—C3A | 123.6 | O12C—C13C—O11C | 123.3 (2) |
O21A—C2A—C1A | 116.0 | O12C—C13C—C12C | 123.7 (2) |
C3A—C2A—C1A | 120.4 | O11C—C13C—C12C | 113.0 (2) |
C4A—C3A—C2A | 119.9 | O21C—C21C—C22C | 107.31 (18) |
C4A—C3A—H3A | 120.1 | O21C—C21C—H21E | 110.3 |
C2A—C3A—H3A | 120.1 | C22C—C21C—H21E | 110.3 |
C3A—C4A—C5A | 120.7 | O21C—C21C—H21F | 110.3 |
C3A—C4A—H4A | 119.7 | C22C—C21C—H21F | 110.3 |
C5A—C4A—H4A | 119.7 | H21E—C21C—H21F | 108.5 |
C6A—C5A—C4A | 119.6 | C21C—C22C—H22G | 109.5 |
C6A—C5A—H5A | 120.2 | C21C—C22C—H22H | 109.5 |
C4A—C5A—H5A | 120.2 | H22G—C22C—H22H | 109.5 |
C5A—C6A—C1A | 121.6 | C21C—C22C—H22I | 109.5 |
C5A—C6A—H6A | 119.2 | H22G—C22C—H22I | 109.5 |
C1A—C6A—H6A | 119.2 | H22H—C22C—H22I | 109.5 |
C12A—C11A—C1A | 128.2 | C13C—O11C—H1C | 109.5 |
C12A—C11A—H11A | 115.9 | C2C—O21C—C21C | 117.62 (16) |
C1A—C11A—H11A | 115.9 | C6D—C1D—C2D | 118.3 (2) |
C11A—C12A—C13A | 122.7 | C6D—C1D—C11D | 123.8 (2) |
C11A—C12A—H12A | 118.7 | C2D—C1D—C11D | 117.6 (2) |
C13A—C12A—H12A | 118.7 | O21D—C2D—C3D | 123.9 (2) |
O12A—C13A—O11A | 124.5 | O21D—C2D—C1D | 115.6 (2) |
O12A—C13A—C12A | 117.5 | C3D—C2D—C1D | 120.5 (2) |
O11A—C13A—C12A | 118.0 | C4D—C3D—C2D | 119.8 (2) |
O21A—C21A—C22A | 107.2 | C4D—C3D—H3D | 120.1 |
O21A—C21A—H21A | 110.3 | C2D—C3D—H3D | 120.1 |
C22A—C21A—H21A | 110.3 | C5D—C4D—C3D | 120.7 (3) |
O21A—C21A—H21B | 110.3 | C5D—C4D—H4D | 119.6 |
C22A—C21A—H21B | 110.3 | C3D—C4D—H4D | 119.6 |
H21A—C21A—H21B | 108.5 | C4D—C5D—C6D | 119.4 (3) |
C21A—C22A—H22A | 109.5 | C4D—C5D—H5D | 120.3 |
C21A—C22A—H22B | 109.5 | C6D—C5D—H5D | 120.3 |
H22A—C22A—H22B | 109.5 | C5D—C6D—C1D | 121.2 (2) |
C21A—C22A—H22C | 109.5 | C5D—C6D—H6D | 119.4 |
H22A—C22A—H22C | 109.5 | C1D—C6D—H6D | 119.4 |
H22B—C22A—H22C | 109.5 | C1D—C11D—C12D | 119.5 (2) |
C13A—O11A—H1A | 109.5 | C1D—C11D—C12E | 115.9 (2) |
C2A—O21A—C21A | 118.8 | C12D—C11D—C12E | 90.37 (18) |
C6B—C1B—C2B | 118.0 | C1D—C11D—H11D | 109.9 |
C6B—C1B—C11B | 120.8 | C12D—C11D—H11D | 109.9 |
C2B—C1B—C11B | 121.2 | C12E—C11D—H11D | 109.9 |
O21B—C2B—C3B | 123.3 | C13D—C12D—C11D | 115.0 (2) |
O21B—C2B—C1B | 116.1 | C13D—C12D—C11E | 112.5 (2) |
C3B—C2B—C1B | 120.6 | C11D—C12D—C11E | 89.80 (17) |
C4B—C3B—C2B | 119.6 | C13D—C12D—H12D | 112.6 |
C4B—C3B—H3B | 120.2 | C11D—C12D—H12D | 112.6 |
C2B—C3B—H3B | 120.2 | C11E—C12D—H12D | 112.6 |
C3B—C4B—C5B | 120.9 | O12D—C13D—O11D | 122.8 (2) |
C3B—C4B—H4B | 119.6 | O12D—C13D—C12D | 123.2 (2) |
C5B—C4B—H4B | 119.6 | O11D—C13D—C12D | 113.6 (2) |
C6B—C5B—C4B | 119.2 | O21D—C21D—C22D | 107.9 (2) |
C6B—C5B—H5B | 120.4 | O21D—C21D—H21G | 110.1 |
C4B—C5B—H5B | 120.4 | C22D—C21D—H21G | 110.1 |
C5B—C6B—C1B | 121.7 | O21D—C21D—H21H | 110.1 |
C5B—C6B—H6B | 119.1 | C22D—C21D—H21H | 110.1 |
C1B—C6B—H6B | 119.1 | H21G—C21D—H21H | 108.4 |
C12B—C11B—C1B | 127.4 | C13D—O11D—H1D | 109.5 |
C12B—C11B—H11B | 116.3 | C2D—O21D—C21D | 118.24 (18) |
C1B—C11B—H11B | 116.3 | C6E—C1E—C2E | 118.1 (2) |
C11B—C12B—C13B | 122.5 | C6E—C1E—C11E | 124.3 (2) |
C11B—C12B—H12B | 118.7 | C2E—C1E—C11E | 117.1 (2) |
C13B—C12B—H12B | 118.7 | O21E—C2E—C3E | 124.2 (2) |
O12B—C13B—O11B | 124.4 | O21E—C2E—C1E | 115.0 (2) |
O12B—C13B—C12B | 120.1 | C3E—C2E—C1E | 120.8 (2) |
O11B—C13B—C12B | 115.4 | C4E—C3E—C2E | 119.5 (2) |
O21B—C21B—C22B | 107.2 | C4E—C3E—H3E | 120.3 |
O21B—C21B—H21C | 110.3 | C2E—C3E—H3E | 120.3 |
C22B—C21B—H21C | 110.3 | C5E—C4E—C3E | 121.2 (2) |
O21B—C21B—H21D | 110.3 | C5E—C4E—H4E | 119.4 |
C22B—C21B—H21D | 110.3 | C3E—C4E—H4E | 119.4 |
H21C—C21B—H21D | 108.5 | C4E—C5E—C6E | 118.7 (3) |
C21B—C22B—H22D | 109.5 | C4E—C5E—H5E | 120.7 |
C21B—C22B—H22E | 109.5 | C6E—C5E—H5E | 120.7 |
H22D—C22B—H22E | 109.5 | C1E—C6E—C5E | 121.8 (2) |
C21B—C22B—H22F | 109.5 | C1E—C6E—H6E | 119.1 |
H22D—C22B—H22F | 109.5 | C5E—C6E—H6E | 119.1 |
H22E—C22B—H22F | 109.5 | C1E—C11E—C12E | 119.8 (2) |
C13B—O11B—H1B | 109.5 | C1E—C11E—C12D | 115.7 (2) |
C2B—O21B—C21B | 118.3 | C12E—C11E—C12D | 90.21 (18) |
C6C—C1C—C2C | 117.6 (2) | C1E—C11E—H11E | 109.9 |
C6C—C1C—C11C | 121.9 (2) | C12E—C11E—H11E | 109.9 |
C2C—C1C—C11C | 120.4 (2) | C12D—C11E—H11E | 109.9 |
O21C—C2C—C3C | 123.7 (2) | C13E—C12E—C11E | 115.6 (2) |
O21C—C2C—C1C | 116.09 (19) | C13E—C12E—C11D | 111.38 (19) |
C3C—C2C—C1C | 120.2 (2) | C11E—C12E—C11D | 89.61 (17) |
C4C—C3C—C2C | 120.1 (2) | C13E—C12E—H12E | 112.8 |
C4C—C3C—H3C | 119.9 | C11E—C12E—H12E | 112.8 |
C2C—C3C—H3C | 119.9 | C11D—C12E—H12E | 112.8 |
C3C—C4C—C5C | 120.9 (2) | O12E—C13E—O11E | 123.8 (2) |
C3C—C4C—H4C | 119.6 | O12E—C13E—C12E | 122.6 (2) |
C5C—C4C—H4C | 119.6 | O11E—C13E—C12E | 113.2 (2) |
C4C—C5C—C6C | 119.0 (2) | O21E—C21E—C22E | 107.72 (19) |
C4C—C5C—H5C | 120.5 | O21E—C21E—H21I | 110.2 |
C6C—C5C—H5C | 120.5 | C22E—C21E—H21I | 110.2 |
C5C—C6C—C1C | 122.0 (2) | O21E—C21E—H21J | 110.2 |
C5C—C6C—H6C | 119.0 | C22E—C21E—H21J | 110.2 |
C1C—C6C—H6C | 119.0 | H21I—C21E—H21J | 108.5 |
C12C—C11C—C1C | 126.3 (2) | C13E—O11E—H1E | 109.5 |
C12C—C11C—H11C | 116.8 | C2E—O21E—C21E | 117.59 (18) |
C1C—C11C—H11C | 116.8 | | |
| | | |
C6A—C1A—C2A—O21A | −179.8 | C6D—C1D—C2D—C3D | 0.3 (4) |
C11A—C1A—C2A—O21A | −3.3 | C11D—C1D—C2D—C3D | −173.7 (2) |
C6A—C1A—C2A—C3A | 1.6 | O21D—C2D—C3D—C4D | −179.6 (2) |
C11A—C1A—C2A—C3A | 178.1 | C1D—C2D—C3D—C4D | −0.4 (4) |
O21A—C2A—C3A—C4A | 179.9 | C2D—C3D—C4D—C5D | 0.1 (4) |
C1A—C2A—C3A—C4A | −1.6 | C3D—C4D—C5D—C6D | 0.3 (4) |
C2A—C3A—C4A—C5A | 0.6 | C4D—C5D—C6D—C1D | −0.5 (4) |
C3A—C4A—C5A—C6A | 0.3 | C2D—C1D—C6D—C5D | 0.1 (4) |
C4A—C5A—C6A—C1A | −0.2 | C11D—C1D—C6D—C5D | 173.7 (3) |
C2A—C1A—C6A—C5A | −0.7 | C6D—C1D—C11D—C12D | 13.4 (4) |
C11A—C1A—C6A—C5A | −177.2 | C2D—C1D—C11D—C12D | −173.0 (2) |
C6A—C1A—C11A—C12A | 0.1 | C6D—C1D—C11D—C12E | −93.0 (3) |
C2A—C1A—C11A—C12A | −176.3 | C2D—C1D—C11D—C12E | 80.6 (3) |
C1A—C11A—C12A—C13A | −179.9 | C1D—C11D—C12D—C13D | 125.7 (2) |
C11A—C12A—C13A—O12A | −0.5 | C12E—C11D—C12D—C13D | −114.0 (2) |
C11A—C12A—C13A—O11A | 179.6 | C1D—C11D—C12D—C11E | −119.5 (2) |
C3A—C2A—O21A—C21A | 1.1 | C12E—C11D—C12D—C11E | 0.89 (17) |
C1A—C2A—O21A—C21A | −177.4 | C11D—C12D—C13D—O12D | 29.2 (4) |
C22A—C21A—O21A—C2A | 175.5 | C11E—C12D—C13D—O12D | −71.7 (3) |
C6B—C1B—C2B—O21B | 179.7 | C11D—C12D—C13D—O11D | −158.2 (2) |
C11B—C1B—C2B—O21B | 2.6 | C11E—C12D—C13D—O11D | 100.9 (2) |
C6B—C1B—C2B—C3B | 0.1 | C3D—C2D—O21D—C21D | 11.6 (4) |
C11B—C1B—C2B—C3B | −177.0 | C1D—C2D—O21D—C21D | −167.5 (2) |
O21B—C2B—C3B—C4B | −179.6 | C22D—C21D—O21D—C2D | 174.3 (2) |
C1B—C2B—C3B—C4B | −0.1 | C6E—C1E—C2E—O21E | 178.3 (2) |
C2B—C3B—C4B—C5B | −0.2 | C11E—C1E—C2E—O21E | −8.8 (3) |
C3B—C4B—C5B—C6B | 0.3 | C6E—C1E—C2E—C3E | −2.2 (4) |
C4B—C5B—C6B—C1B | −0.3 | C11E—C1E—C2E—C3E | 170.7 (2) |
C2B—C1B—C6B—C5B | 0.1 | O21E—C2E—C3E—C4E | −179.9 (2) |
C11B—C1B—C6B—C5B | 177.2 | C1E—C2E—C3E—C4E | 0.6 (4) |
C6B—C1B—C11B—C12B | 8.9 | C2E—C3E—C4E—C5E | 1.5 (4) |
C2B—C1B—C11B—C12B | −174.1 | C3E—C4E—C5E—C6E | −2.0 (4) |
C1B—C11B—C12B—C13B | 179.5 | C2E—C1E—C6E—C5E | 1.7 (4) |
C11B—C12B—C13B—O12B | 6.2 | C11E—C1E—C6E—C5E | −170.7 (3) |
C11B—C12B—C13B—O11B | −173.4 | C4E—C5E—C6E—C1E | 0.4 (4) |
C3B—C2B—O21B—C21B | −3.4 | C6E—C1E—C11E—C12E | −6.2 (4) |
C1B—C2B—O21B—C21B | 177.0 | C2E—C1E—C11E—C12E | −178.6 (2) |
C22B—C21B—O21B—C2B | −175.8 | C6E—C1E—C11E—C12D | 100.1 (3) |
C6C—C1C—C2C—O21C | 176.2 (2) | C2E—C1E—C11E—C12D | −72.4 (3) |
C11C—C1C—C2C—O21C | −6.6 (3) | C13D—C12D—C11E—C1E | −7.3 (3) |
C6C—C1C—C2C—C3C | −4.7 (4) | C11D—C12D—C11E—C1E | −124.5 (2) |
C11C—C1C—C2C—C3C | 172.5 (2) | C13D—C12D—C11E—C12E | 116.2 (2) |
O21C—C2C—C3C—C4C | −177.6 (2) | C11D—C12D—C11E—C12E | −0.92 (18) |
C1C—C2C—C3C—C4C | 3.4 (4) | C1E—C11E—C12E—C13E | −125.4 (3) |
C2C—C3C—C4C—C5C | 0.3 (4) | C12D—C11E—C12E—C13E | 114.5 (2) |
C3C—C4C—C5C—C6C | −2.4 (4) | C1E—C11E—C12E—C11D | 120.9 (2) |
C4C—C5C—C6C—C1C | 0.9 (4) | C12D—C11E—C12E—C11D | 0.88 (17) |
C2C—C1C—C6C—C5C | 2.6 (4) | C1D—C11D—C12E—C13E | 5.0 (3) |
C11C—C1C—C6C—C5C | −174.5 (2) | C12D—C11D—C12E—C13E | −118.4 (2) |
C6C—C1C—C11C—C12C | 2.6 (4) | C1D—C11D—C12E—C11E | 122.4 (2) |
C2C—C1C—C11C—C12C | −174.5 (2) | C12D—C11D—C12E—C11E | −0.91 (18) |
C1C—C11C—C12C—C13C | 174.6 (2) | C11E—C12E—C13E—O12E | −20.7 (3) |
C11C—C12C—C13C—O12C | 7.1 (4) | C11D—C12E—C13E—O12E | 79.6 (3) |
C11C—C12C—C13C—O11C | −171.3 (2) | C11E—C12E—C13E—O11E | 165.4 (2) |
C3C—C2C—O21C—C21C | 5.9 (3) | C11D—C12E—C13E—O11E | −94.3 (2) |
C1C—C2C—O21C—C21C | −175.0 (2) | C3E—C2E—O21E—C21E | −17.2 (4) |
C22C—C21C—O21C—C2C | 176.9 (2) | C1E—C2E—O21E—C21E | 162.2 (2) |
C6D—C1D—C2D—O21D | 179.5 (2) | C22E—C21E—O21E—C2E | −169.7 (2) |
C11D—C1D—C2D—O21D | 5.6 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11A—H1A···O12Di | 0.84 | 1.66 | 2.472 (11) | 163 |
O11D—H1D···O12Ai | 0.84 | 2.02 | 2.702 (11) | 138 |
O11D—H1D···O12Di | 0.84 | 1.98 | 2.718 (3) | 146 |
O11C—H1C···O12Eii | 0.84 | 1.84 | 2.672 (2) | 172 |
O11E—H1E···O12Cii | 0.84 | 1.83 | 2.648 (2) | 163 |
O11C—H1C···O12Bii | 0.84 | 1.75 | 2.584 (12) | 172 |
O11B—H1B···O12Cii | 0.84 | 1.69 | 2.515 (12) | 167 |
O11A—H1A···O12Ai | 0.84 | 1.72 | 2.51 (2) | 156 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z+1. |
(rd48hlts) (
E)-3-(2-Ethoxyphenyl)propenoic acid and
trans-2,4-bis(2-ethoxyphenyl)-
trans-1,3-cyclobutane-dicarboxylic acid
top
Crystal data top
C22H24O6·C11H12O3 | Z = 2 |
Mr = 576.62 | F(000) = 612 |
Triclinic, P1 | Dx = 1.304 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3099 (12) Å | Cell parameters from 794 reflections |
b = 11.0026 (16) Å | θ = 2.5–28.1° |
c = 17.471 (3) Å | µ = 0.10 mm−1 |
α = 99.768 (3)° | T = 173 K |
β = 91.912 (3)° | Irregular, white |
γ = 110.392 (3)° | 0.45 × 0.24 × 0.14 mm |
V = 1468.1 (4) Å3 | |
Data collection top
CCD area detector diffractometer | 3394 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 25.5°, θmin = 1.2° |
phi and ω scans | h = −10→10 |
8381 measured reflections | k = −13→7 |
5409 independent reflections | l = −21→19 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0523P)2] where P = (Fo2 + 2Fc2)/3 |
5409 reflections | (Δ/σ)max = 0.001 |
397 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Crystal data top
C22H24O6·C11H12O3 | γ = 110.392 (3)° |
Mr = 576.62 | V = 1468.1 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.3099 (12) Å | Mo Kα radiation |
b = 11.0026 (16) Å | µ = 0.10 mm−1 |
c = 17.471 (3) Å | T = 173 K |
α = 99.768 (3)° | 0.45 × 0.24 × 0.14 mm |
β = 91.912 (3)° | |
Data collection top
CCD area detector diffractometer | 3394 reflections with I > 2σ(I) |
8381 measured reflections | Rint = 0.028 |
5409 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.18 e Å−3 |
5409 reflections | Δρmin = −0.22 e Å−3 |
397 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 | |
C1C | 0.2135 (2) | 0.64754 (18) | 0.41729 (10) | 0.0285 (4) | |
C2C | 0.2140 (2) | 0.63657 (18) | 0.33616 (10) | 0.0282 (4) | |
C3C | 0.0612 (2) | 0.6078 (2) | 0.28917 (11) | 0.0372 (5) | |
H3C | 0.0609 | 0.5957 | 0.2340 | 0.045* | |
C4C | −0.0896 (2) | 0.5969 (2) | 0.32331 (12) | 0.0399 (5) | |
H4C | −0.1937 | 0.5765 | 0.2912 | 0.048* | |
C5C | −0.0912 (2) | 0.6153 (2) | 0.40344 (12) | 0.0393 (5) | |
H5C | −0.1941 | 0.6119 | 0.4266 | 0.047* | |
C6C | 0.0588 (2) | 0.63878 (19) | 0.44919 (11) | 0.0357 (5) | |
H6C | 0.0569 | 0.6493 | 0.5042 | 0.043* | |
C11C | 0.3682 (2) | 0.66037 (17) | 0.46543 (10) | 0.0294 (4) | |
H11C | 0.4694 | 0.6683 | 0.4398 | 0.035* | |
C12C | 0.3807 (2) | 0.66192 (19) | 0.54180 (11) | 0.0347 (5) | |
H12C | 0.2860 | 0.6639 | 0.5703 | 0.042* | |
C13C | 0.5356 (2) | 0.66068 (19) | 0.58309 (11) | 0.0335 (5) | |
C21C | 0.3780 (2) | 0.6567 (2) | 0.22554 (10) | 0.0356 (5) | |
H21E | 0.3317 | 0.7223 | 0.2113 | 0.043* | |
H21F | 0.3086 | 0.5687 | 0.1941 | 0.043* | |
C22C | 0.5638 (2) | 0.6932 (2) | 0.21001 (11) | 0.0462 (6) | |
H22G | 0.6331 | 0.7756 | 0.2455 | 0.069* | |
H22H | 0.5751 | 0.7052 | 0.1559 | 0.069* | |
H22I | 0.6045 | 0.6225 | 0.2185 | 0.069* | |
O11C | 0.51430 (18) | 0.64305 (17) | 0.65539 (8) | 0.0504 (4) | |
O12C | 0.67170 (17) | 0.67357 (14) | 0.55422 (7) | 0.0410 (4) | |
O21C | 0.36971 (15) | 0.65443 (13) | 0.30720 (7) | 0.0345 (3) | |
C1D | 1.0113 (2) | 0.03434 (17) | 0.23138 (10) | 0.0265 (4) | |
C2D | 0.9924 (2) | −0.01048 (18) | 0.30228 (10) | 0.0295 (4) | |
C3D | 1.1192 (2) | −0.0471 (2) | 0.33565 (11) | 0.0378 (5) | |
H3D | 1.1043 | −0.0791 | 0.3831 | 0.045* | |
C4D | 1.2666 (3) | −0.0364 (2) | 0.29876 (12) | 0.0417 (5) | |
H4D | 1.3542 | −0.0597 | 0.3217 | 0.050* | |
C5D | 1.2886 (2) | 0.0077 (2) | 0.22908 (12) | 0.0392 (5) | |
H5D | 1.3901 | 0.0143 | 0.2040 | 0.047* | |
C6D | 1.1602 (2) | 0.04226 (19) | 0.19620 (11) | 0.0332 (5) | |
H6D | 1.1752 | 0.0722 | 0.1481 | 0.040* | |
C11D | 0.8743 (2) | 0.08014 (18) | 0.20145 (9) | 0.0268 (4) | |
H11D | 0.7573 | 0.0180 | 0.2083 | 0.032* | |
C12D | 0.8767 (2) | 0.11147 (17) | 0.11821 (10) | 0.0271 (4) | |
H12D | 0.9794 | 0.1046 | 0.0922 | 0.033* | |
C13D | 0.7110 (2) | 0.04202 (18) | 0.06647 (10) | 0.0279 (4) | |
C21D | 0.8335 (3) | −0.0313 (2) | 0.41481 (10) | 0.0412 (5) | |
H21G | 0.9336 | 0.0367 | 0.4483 | 0.049* | |
H21H | 0.8344 | −0.1195 | 0.4194 | 0.049* | |
C22D | 0.6688 (3) | −0.0176 (2) | 0.43986 (11) | 0.0463 (6) | |
H22J | 0.6706 | 0.0708 | 0.4364 | 0.069* | |
H22K | 0.6575 | −0.0302 | 0.4939 | 0.069* | |
H22L | 0.5708 | −0.0843 | 0.4057 | 0.069* | |
O11D | 0.73184 (17) | 0.03306 (14) | −0.00878 (7) | 0.0375 (4) | |
O12D | 0.56985 (15) | 0.00372 (13) | 0.09095 (7) | 0.0347 (3) | |
O21D | 0.84324 (15) | −0.01509 (13) | 0.33532 (7) | 0.0336 (3) | |
C1E | 0.7655 (2) | 0.30836 (18) | 0.12373 (10) | 0.0274 (4) | |
C2E | 0.7772 (2) | 0.33581 (18) | 0.04820 (10) | 0.0301 (4) | |
C3E | 0.6466 (2) | 0.36397 (19) | 0.01178 (11) | 0.0384 (5) | |
H3E | 0.6542 | 0.3814 | −0.0397 | 0.046* | |
C4E | 0.5056 (3) | 0.3665 (2) | 0.05080 (12) | 0.0408 (5) | |
H4E | 0.4160 | 0.3849 | 0.0257 | 0.049* | |
C5E | 0.4933 (2) | 0.3427 (2) | 0.12556 (12) | 0.0384 (5) | |
H5E | 0.3967 | 0.3459 | 0.1523 | 0.046* | |
C6E | 0.6242 (2) | 0.31384 (19) | 0.16162 (11) | 0.0342 (5) | |
H6E | 0.6160 | 0.2976 | 0.2133 | 0.041* | |
C11E | 0.8994 (2) | 0.25993 (18) | 0.15495 (10) | 0.0270 (4) | |
H11E | 1.0177 | 0.3208 | 0.1487 | 0.032* | |
C12E | 0.8938 (2) | 0.22830 (18) | 0.23735 (10) | 0.0276 (4) | |
H12E | 0.7897 | 0.2343 | 0.2624 | 0.033* | |
C13E | 1.0573 (2) | 0.29663 (18) | 0.29063 (10) | 0.0272 (4) | |
C21E | 0.9170 (2) | 0.3160 (2) | −0.06918 (10) | 0.0371 (5) | |
H21I | 0.9183 | 0.3985 | −0.0851 | 0.045* | |
H21J | 0.8103 | 0.2432 | −0.0943 | 0.045* | |
C22E | 1.0720 (2) | 0.2861 (2) | −0.09369 (11) | 0.0447 (6) | |
H22M | 1.1768 | 0.3612 | −0.0713 | 0.067* | |
H22N | 1.0679 | 0.2704 | −0.1508 | 0.067* | |
H22O | 1.0729 | 0.2071 | −0.0751 | 0.067* | |
O11E | 1.03755 (17) | 0.29178 (13) | 0.36453 (7) | 0.0355 (3) | |
O12E | 1.19807 (15) | 0.34447 (12) | 0.26650 (7) | 0.0325 (3) | |
O21E | 0.92193 (15) | 0.33064 (13) | 0.01424 (7) | 0.0343 (3) | |
H1D | 0.625 (3) | 0.009 (2) | −0.0368 (13) | 0.071 (8)* | |
H1C | 0.611 (3) | 0.648 (2) | 0.6797 (14) | 0.078 (9)* | |
H1E | 1.151 (3) | 0.317 (2) | 0.3959 (14) | 0.086 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1C | 0.0300 (10) | 0.0265 (11) | 0.0292 (11) | 0.0095 (9) | 0.0019 (8) | 0.0075 (8) |
C2C | 0.0291 (10) | 0.0289 (11) | 0.0277 (11) | 0.0118 (9) | 0.0018 (8) | 0.0059 (8) |
C3C | 0.0361 (11) | 0.0459 (13) | 0.0305 (11) | 0.0157 (10) | −0.0027 (9) | 0.0089 (10) |
C4C | 0.0305 (11) | 0.0480 (14) | 0.0432 (13) | 0.0161 (10) | −0.0046 (9) | 0.0119 (10) |
C5C | 0.0319 (11) | 0.0460 (13) | 0.0454 (13) | 0.0181 (10) | 0.0054 (10) | 0.0137 (10) |
C6C | 0.0381 (11) | 0.0394 (12) | 0.0310 (11) | 0.0152 (10) | 0.0049 (9) | 0.0081 (9) |
C11C | 0.0285 (10) | 0.0293 (11) | 0.0278 (11) | 0.0081 (9) | −0.0007 (8) | 0.0043 (8) |
C12C | 0.0301 (11) | 0.0429 (13) | 0.0302 (11) | 0.0118 (10) | 0.0002 (8) | 0.0083 (9) |
C13C | 0.0351 (11) | 0.0376 (12) | 0.0236 (11) | 0.0093 (10) | −0.0010 (9) | 0.0041 (9) |
C21C | 0.0393 (12) | 0.0440 (13) | 0.0251 (11) | 0.0167 (10) | 0.0017 (9) | 0.0075 (9) |
C22C | 0.0408 (12) | 0.0602 (15) | 0.0324 (12) | 0.0125 (12) | 0.0022 (9) | 0.0070 (11) |
O11C | 0.0342 (9) | 0.0872 (13) | 0.0292 (9) | 0.0170 (9) | −0.0018 (7) | 0.0214 (8) |
O12C | 0.0366 (8) | 0.0626 (10) | 0.0257 (7) | 0.0212 (7) | 0.0001 (6) | 0.0072 (7) |
O21C | 0.0310 (7) | 0.0499 (9) | 0.0232 (7) | 0.0147 (7) | 0.0012 (6) | 0.0089 (6) |
C1D | 0.0266 (10) | 0.0240 (10) | 0.0259 (10) | 0.0072 (8) | −0.0032 (8) | 0.0019 (8) |
C2D | 0.0293 (10) | 0.0284 (11) | 0.0287 (10) | 0.0086 (9) | −0.0033 (8) | 0.0046 (8) |
C3D | 0.0417 (12) | 0.0429 (13) | 0.0347 (11) | 0.0208 (10) | −0.0032 (9) | 0.0128 (10) |
C4D | 0.0388 (12) | 0.0484 (14) | 0.0440 (13) | 0.0253 (11) | −0.0064 (10) | 0.0067 (11) |
C5D | 0.0312 (11) | 0.0479 (14) | 0.0415 (12) | 0.0203 (10) | 0.0023 (9) | 0.0042 (10) |
C6D | 0.0349 (11) | 0.0372 (12) | 0.0286 (11) | 0.0153 (10) | 0.0007 (9) | 0.0052 (9) |
C11D | 0.0237 (10) | 0.0340 (11) | 0.0227 (10) | 0.0101 (9) | −0.0006 (8) | 0.0067 (8) |
C12D | 0.0256 (10) | 0.0333 (11) | 0.0244 (10) | 0.0131 (9) | 0.0014 (8) | 0.0052 (8) |
C13D | 0.0310 (11) | 0.0295 (11) | 0.0240 (11) | 0.0120 (9) | 0.0007 (8) | 0.0050 (8) |
C21D | 0.0450 (12) | 0.0564 (14) | 0.0265 (11) | 0.0202 (11) | 0.0005 (9) | 0.0153 (10) |
C22D | 0.0463 (13) | 0.0609 (15) | 0.0348 (12) | 0.0205 (12) | 0.0081 (10) | 0.0144 (11) |
O11D | 0.0319 (8) | 0.0533 (9) | 0.0213 (7) | 0.0103 (7) | −0.0022 (6) | 0.0026 (6) |
O12D | 0.0278 (7) | 0.0467 (9) | 0.0248 (7) | 0.0076 (7) | −0.0021 (6) | 0.0078 (6) |
O21D | 0.0297 (7) | 0.0483 (9) | 0.0260 (7) | 0.0149 (7) | 0.0009 (6) | 0.0144 (6) |
C1E | 0.0264 (10) | 0.0259 (10) | 0.0284 (10) | 0.0087 (8) | −0.0042 (8) | 0.0036 (8) |
C2E | 0.0304 (10) | 0.0291 (11) | 0.0282 (10) | 0.0085 (9) | −0.0034 (8) | 0.0046 (8) |
C3E | 0.0437 (12) | 0.0416 (13) | 0.0322 (11) | 0.0166 (11) | −0.0043 (9) | 0.0121 (9) |
C4E | 0.0386 (12) | 0.0435 (13) | 0.0452 (13) | 0.0205 (11) | −0.0062 (10) | 0.0112 (10) |
C5E | 0.0332 (11) | 0.0437 (13) | 0.0439 (13) | 0.0207 (10) | 0.0025 (9) | 0.0082 (10) |
C6E | 0.0356 (11) | 0.0401 (12) | 0.0299 (11) | 0.0171 (10) | 0.0009 (9) | 0.0075 (9) |
C11E | 0.0251 (9) | 0.0327 (11) | 0.0225 (10) | 0.0096 (9) | −0.0019 (8) | 0.0058 (8) |
C12E | 0.0262 (10) | 0.0376 (12) | 0.0219 (9) | 0.0155 (9) | 0.0004 (8) | 0.0053 (8) |
C13E | 0.0347 (11) | 0.0280 (11) | 0.0225 (10) | 0.0165 (9) | −0.0002 (8) | 0.0033 (8) |
C21E | 0.0428 (12) | 0.0434 (13) | 0.0232 (10) | 0.0126 (10) | −0.0004 (9) | 0.0083 (9) |
C22E | 0.0464 (13) | 0.0532 (15) | 0.0315 (12) | 0.0156 (11) | 0.0036 (10) | 0.0052 (10) |
O11E | 0.0380 (8) | 0.0486 (9) | 0.0195 (7) | 0.0172 (7) | −0.0017 (6) | 0.0030 (6) |
O12E | 0.0308 (7) | 0.0374 (8) | 0.0266 (7) | 0.0085 (6) | −0.0019 (6) | 0.0078 (6) |
O21E | 0.0335 (7) | 0.0474 (9) | 0.0238 (7) | 0.0155 (7) | 0.0007 (6) | 0.0106 (6) |
Geometric parameters (Å, º) top
C1C—C6C | 1.398 (2) | C11D—H11D | 1.0000 |
C1C—C2C | 1.402 (2) | C12D—C13D | 1.499 (2) |
C1C—C11C | 1.463 (2) | C12D—C11E | 1.593 (2) |
C2C—O21C | 1.367 (2) | C12D—H12D | 1.0000 |
C2C—C3C | 1.396 (2) | C13D—O12D | 1.220 (2) |
C3C—C4C | 1.382 (2) | C13D—O11D | 1.323 (2) |
C3C—H3C | 0.9500 | C21D—O21D | 1.431 (2) |
C4C—C5C | 1.381 (3) | C21D—C22D | 1.499 (3) |
C4C—H4C | 0.9500 | C21D—H21G | 0.9900 |
C5C—C6C | 1.378 (3) | C21D—H21H | 0.9900 |
C5C—H5C | 0.9500 | C22D—H22J | 0.9800 |
C6C—H6C | 0.9500 | C22D—H22K | 0.9800 |
C11C—C12C | 1.332 (2) | C22D—H22L | 0.9800 |
C11C—H11C | 0.9500 | O11D—H1D | 0.93 (2) |
C12C—C13C | 1.459 (3) | C1E—C6E | 1.381 (2) |
C12C—H12C | 0.9500 | C1E—C2E | 1.402 (2) |
C13C—O12C | 1.227 (2) | C1E—C11E | 1.514 (2) |
C13C—O11C | 1.319 (2) | C2E—O21E | 1.373 (2) |
C21C—O21C | 1.435 (2) | C2E—C3E | 1.391 (3) |
C21C—C22C | 1.500 (2) | C3E—C4E | 1.381 (3) |
C21C—H21E | 0.9900 | C3E—H3E | 0.9500 |
C21C—H21F | 0.9900 | C4E—C5E | 1.375 (3) |
C22C—H22G | 0.9800 | C4E—H4E | 0.9500 |
C22C—H22H | 0.9800 | C5E—C6E | 1.394 (3) |
C22C—H22I | 0.9800 | C5E—H5E | 0.9500 |
O11C—H1C | 0.87 (2) | C6E—H6E | 0.9500 |
C1D—C6D | 1.382 (2) | C11E—C12E | 1.536 (2) |
C1D—C2D | 1.403 (2) | C11E—H11E | 1.0000 |
C1D—C11D | 1.507 (2) | C12E—C13E | 1.498 (2) |
C2D—O21D | 1.373 (2) | C12E—H12E | 1.0000 |
C2D—C3D | 1.396 (2) | C13E—O12E | 1.225 (2) |
C3D—C4D | 1.381 (3) | C13E—O11E | 1.315 (2) |
C3D—H3D | 0.9500 | C21E—O21E | 1.436 (2) |
C4D—C5D | 1.380 (3) | C21E—C22E | 1.495 (3) |
C4D—H4D | 0.9500 | C21E—H21I | 0.9900 |
C5D—C6D | 1.388 (3) | C21E—H21J | 0.9900 |
C5D—H5D | 0.9500 | C22E—H22M | 0.9800 |
C6D—H6D | 0.9500 | C22E—H22N | 0.9800 |
C11D—C12D | 1.550 (2) | C22E—H22O | 0.9800 |
C11D—C12E | 1.594 (2) | O11E—H1E | 1.00 (3) |
| | | |
C6C—C1C—C2C | 117.67 (16) | C13D—C12D—H12D | 112.8 |
C6C—C1C—C11C | 121.85 (16) | C11D—C12D—H12D | 112.8 |
C2C—C1C—C11C | 120.39 (16) | C11E—C12D—H12D | 112.8 |
O21C—C2C—C3C | 123.24 (16) | O12D—C13D—O11D | 123.02 (16) |
O21C—C2C—C1C | 116.35 (15) | O12D—C13D—C12D | 123.59 (16) |
C3C—C2C—C1C | 120.41 (17) | O11D—C13D—C12D | 113.28 (16) |
C4C—C3C—C2C | 119.66 (18) | O21D—C21D—C22D | 107.72 (15) |
C4C—C3C—H3C | 120.2 | O21D—C21D—H21G | 110.2 |
C2C—C3C—H3C | 120.2 | C22D—C21D—H21G | 110.2 |
C5C—C4C—C3C | 120.97 (18) | O21D—C21D—H21H | 110.2 |
C5C—C4C—H4C | 119.5 | C22D—C21D—H21H | 110.2 |
C3C—C4C—H4C | 119.5 | H21G—C21D—H21H | 108.5 |
C6C—C5C—C4C | 118.95 (18) | C21D—C22D—H22J | 109.5 |
C6C—C5C—H5C | 120.5 | C21D—C22D—H22K | 109.5 |
C4C—C5C—H5C | 120.5 | H22J—C22D—H22K | 109.5 |
C5C—C6C—C1C | 122.15 (18) | C21D—C22D—H22L | 109.5 |
C5C—C6C—H6C | 118.9 | H22J—C22D—H22L | 109.5 |
C1C—C6C—H6C | 118.9 | H22K—C22D—H22L | 109.5 |
C12C—C11C—C1C | 126.20 (17) | C13D—O11D—H1D | 108.9 (14) |
C12C—C11C—H11C | 116.9 | C2D—O21D—C21D | 117.94 (14) |
C1C—C11C—H11C | 116.9 | C6E—C1E—C2E | 118.45 (16) |
C11C—C12C—C13C | 122.01 (18) | C6E—C1E—C11E | 123.96 (16) |
C11C—C12C—H12C | 119.0 | C2E—C1E—C11E | 117.23 (16) |
C13C—C12C—H12C | 119.0 | O21E—C2E—C3E | 124.00 (17) |
O12C—C13C—O11C | 122.82 (18) | O21E—C2E—C1E | 115.58 (16) |
O12C—C13C—C12C | 124.26 (18) | C3E—C2E—C1E | 120.41 (18) |
O11C—C13C—C12C | 112.92 (18) | C4E—C3E—C2E | 119.65 (18) |
O21C—C21C—C22C | 107.66 (14) | C4E—C3E—H3E | 120.2 |
O21C—C21C—H21E | 110.2 | C2E—C3E—H3E | 120.2 |
C22C—C21C—H21E | 110.2 | C5E—C4E—C3E | 120.90 (18) |
O21C—C21C—H21F | 110.2 | C5E—C4E—H4E | 119.5 |
C22C—C21C—H21F | 110.2 | C3E—C4E—H4E | 119.5 |
H21E—C21C—H21F | 108.5 | C4E—C5E—C6E | 119.19 (19) |
C21C—C22C—H22G | 109.5 | C4E—C5E—H5E | 120.4 |
C21C—C22C—H22H | 109.5 | C6E—C5E—H5E | 120.4 |
H22G—C22C—H22H | 109.5 | C1E—C6E—C5E | 121.36 (18) |
C21C—C22C—H22I | 109.5 | C1E—C6E—H6E | 119.3 |
H22G—C22C—H22I | 109.5 | C5E—C6E—H6E | 119.3 |
H22H—C22C—H22I | 109.5 | C1E—C11E—C12E | 119.79 (15) |
C13C—O11C—H1C | 111.0 (16) | C1E—C11E—C12D | 115.27 (14) |
C2C—O21C—C21C | 117.72 (13) | C12E—C11E—C12D | 90.64 (13) |
C6D—C1D—C2D | 117.84 (17) | C1E—C11E—H11E | 109.9 |
C6D—C1D—C11D | 124.08 (17) | C12E—C11E—H11E | 109.9 |
C2D—C1D—C11D | 117.92 (16) | C12D—C11E—H11E | 109.9 |
O21D—C2D—C3D | 123.45 (17) | C13E—C12E—C11E | 115.75 (15) |
O21D—C2D—C1D | 115.60 (16) | C13E—C12E—C11D | 110.71 (14) |
C3D—C2D—C1D | 120.95 (18) | C11E—C12E—C11D | 89.85 (13) |
C4D—C3D—C2D | 119.15 (18) | C13E—C12E—H12E | 112.8 |
C4D—C3D—H3D | 120.4 | C11E—C12E—H12E | 112.8 |
C2D—C3D—H3D | 120.4 | C11D—C12E—H12E | 112.8 |
C5D—C4D—C3D | 121.02 (19) | O12E—C13E—O11E | 123.30 (17) |
C5D—C4D—H4D | 119.5 | O12E—C13E—C12E | 122.65 (16) |
C3D—C4D—H4D | 119.5 | O11E—C13E—C12E | 113.87 (16) |
C4D—C5D—C6D | 119.09 (19) | O21E—C21E—C22E | 107.91 (15) |
C4D—C5D—H5D | 120.5 | O21E—C21E—H21I | 110.1 |
C6D—C5D—H5D | 120.5 | C22E—C21E—H21I | 110.1 |
C1D—C6D—C5D | 121.93 (19) | O21E—C21E—H21J | 110.1 |
C1D—C6D—H6D | 119.0 | C22E—C21E—H21J | 110.1 |
C5D—C6D—H6D | 119.0 | H21I—C21E—H21J | 108.4 |
C1D—C11D—C12D | 119.35 (15) | C21E—C22E—H22M | 109.5 |
C1D—C11D—C12E | 115.79 (14) | C21E—C22E—H22N | 109.5 |
C12D—C11D—C12E | 90.11 (13) | H22M—C22E—H22N | 109.5 |
C1D—C11D—H11D | 110.0 | C21E—C22E—H22O | 109.5 |
C12D—C11D—H11D | 110.0 | H22M—C22E—H22O | 109.5 |
C12E—C11D—H11D | 110.0 | H22N—C22E—H22O | 109.5 |
C13D—C12D—C11D | 115.32 (14) | C13E—O11E—H1E | 111.3 (13) |
C13D—C12D—C11E | 111.78 (14) | C2E—O21E—C21E | 117.75 (14) |
C11D—C12D—C11E | 89.39 (12) | | |
| | | |
C6C—C1C—C2C—O21C | 175.72 (16) | C11D—C12D—C13D—O11D | −157.79 (15) |
C11C—C1C—C2C—O21C | −7.5 (3) | C11E—C12D—C13D—O11D | 102.06 (18) |
C6C—C1C—C2C—C3C | −4.8 (3) | C3D—C2D—O21D—C21D | 13.5 (3) |
C11C—C1C—C2C—C3C | 171.93 (18) | C1D—C2D—O21D—C21D | −166.41 (16) |
O21C—C2C—C3C—C4C | −177.16 (17) | C22D—C21D—O21D—C2D | 173.53 (16) |
C1C—C2C—C3C—C4C | 3.4 (3) | C6E—C1E—C2E—O21E | 179.06 (16) |
C2C—C3C—C4C—C5C | 0.6 (3) | C11E—C1E—C2E—O21E | −7.5 (2) |
C3C—C4C—C5C—C6C | −3.0 (3) | C6E—C1E—C2E—C3E | −1.9 (3) |
C4C—C5C—C6C—C1C | 1.5 (3) | C11E—C1E—C2E—C3E | 171.59 (17) |
C2C—C1C—C6C—C5C | 2.4 (3) | O21E—C2E—C3E—C4E | 179.81 (17) |
C11C—C1C—C6C—C5C | −174.30 (19) | C1E—C2E—C3E—C4E | 0.8 (3) |
C6C—C1C—C11C—C12C | 1.8 (3) | C2E—C3E—C4E—C5E | 0.6 (3) |
C2C—C1C—C11C—C12C | −174.82 (19) | C3E—C4E—C5E—C6E | −0.9 (3) |
C1C—C11C—C12C—C13C | 173.18 (18) | C2E—C1E—C6E—C5E | 1.5 (3) |
C11C—C12C—C13C—O12C | 8.8 (3) | C11E—C1E—C6E—C5E | −171.44 (18) |
C11C—C12C—C13C—O11C | −170.66 (18) | C4E—C5E—C6E—C1E | −0.2 (3) |
C3C—C2C—O21C—C21C | 6.5 (3) | C6E—C1E—C11E—C12E | −7.0 (3) |
C1C—C2C—O21C—C21C | −174.05 (16) | C2E—C1E—C11E—C12E | 179.91 (16) |
C22C—C21C—O21C—C2C | 173.43 (16) | C6E—C1E—C11E—C12D | 99.5 (2) |
C6D—C1D—C2D—O21D | 179.27 (16) | C2E—C1E—C11E—C12D | −73.6 (2) |
C11D—C1D—C2D—O21D | 3.6 (2) | C13D—C12D—C11E—C1E | −7.5 (2) |
C6D—C1D—C2D—C3D | −0.7 (3) | C11D—C12D—C11E—C1E | −124.64 (15) |
C11D—C1D—C2D—C3D | −176.28 (17) | C13D—C12D—C11E—C12E | 116.19 (15) |
O21D—C2D—C3D—C4D | −178.63 (17) | C11D—C12D—C11E—C12E | −0.95 (13) |
C1D—C2D—C3D—C4D | 1.3 (3) | C1E—C11E—C12E—C13E | −126.16 (18) |
C2D—C3D—C4D—C5D | −1.1 (3) | C12D—C11E—C12E—C13E | 113.96 (16) |
C3D—C4D—C5D—C6D | 0.4 (3) | C1E—C11E—C12E—C11D | 120.81 (16) |
C2D—C1D—C6D—C5D | −0.1 (3) | C12D—C11E—C12E—C11D | 0.92 (12) |
C11D—C1D—C6D—C5D | 175.20 (18) | C1D—C11D—C12E—C13E | 4.5 (2) |
C4D—C5D—C6D—C1D | 0.3 (3) | C12D—C11D—C12E—C13E | −118.56 (15) |
C6D—C1D—C11D—C12D | 13.3 (3) | C1D—C11D—C12E—C11E | 122.10 (16) |
C2D—C1D—C11D—C12D | −171.41 (15) | C12D—C11D—C12E—C11E | −0.95 (13) |
C6D—C1D—C11D—C12E | −92.7 (2) | C11E—C12E—C13E—O12E | −19.5 (3) |
C2D—C1D—C11D—C12E | 82.7 (2) | C11D—C12E—C13E—O12E | 80.8 (2) |
C1D—C11D—C12D—C13D | 126.99 (18) | C11E—C12E—C13E—O11E | 165.26 (15) |
C12E—C11D—C12D—C13D | −113.00 (16) | C11D—C12E—C13E—O11E | −94.42 (18) |
C1D—C11D—C12D—C11E | −119.10 (16) | C3E—C2E—O21E—C21E | −18.3 (3) |
C12E—C11D—C12D—C11E | 0.92 (12) | C1E—C2E—O21E—C21E | 160.70 (16) |
C11D—C12D—C13D—O12D | 25.9 (3) | C22E—C21E—O21E—C2E | −168.97 (16) |
C11E—C12D—C13D—O12D | −74.2 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11D—H1D···O12Di | 0.93 (2) | 1.80 (2) | 2.7139 (18) | 169 (2) |
O11C—H1C···O12Eii | 0.87 (2) | 1.79 (2) | 2.6616 (18) | 177 (2) |
O11E—H1E···O12Cii | 1.00 (3) | 1.65 (3) | 2.6350 (18) | 169 (2) |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z+1. |
Experimental details
| (d6hlt_s) | (d12hlt_s) | (rd24hlts) | (rd36hlts) |
Crystal data |
Chemical formula | 0.124(C22H24O6)·2.752(C11H12O3) | 0.219(C22H24O6)·2.562(C11H12O3) | 0.680(C22H24O6)·1.640(C11H12O3) | 0.912(C22H24O6)·1.176(C11H12O3) |
Mr | 576.62 | 576.62 | 576.62 | 576.62 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 173 | 173 | 173 | 173 |
a, b, c (Å) | 8.6452 (13), 10.8577 (17), 17.262 (3) | 8.6164 (10), 10.8765 (14), 17.292 (2) | 8.4919 (13), 10.9148 (17), 17.372 (3) | 8.3863 (13), 10.9711 (18), 17.427 (3) |
α, β, γ (°) | 92.470 (3), 92.102 (3), 112.563 (3) | 93.157 (2), 92.001 (2), 112.657 (3) | 96.027 (3), 91.772 (3), 111.956 (3) | 98.323 (3), 91.809 (3), 111.336 (3) |
V (Å3) | 1492.4 (4) | 1490.4 (3) | 1480.8 (4) | 1471.6 (4) |
Z | 2 | 2 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.09 | 0.09 | 0.09 |
Crystal size (mm) | 0.38 × 0.33 × 0.24 | 0.45 × 0.24 × 0.14 | 0.45 × 0.24 × 0.14 | 0.45 × 0.24 × 0.14 |
|
Data collection |
Diffractometer | CCD area detector diffractometer | CCD area detector diffractometer | CCD area detector diffractometer | CCD area detector diffractometer |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8177, 5500, 3167 | 8551, 5499, 2989 | 8447, 5471, 2825 | 8385, 5439, 3015 |
Rint | 0.022 | 0.023 | 0.030 | 0.028 |
(sin θ/λ)max (Å−1) | 0.606 | 0.606 | 0.606 | 0.606 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.136, 1.03 | 0.053, 0.142, 1.00 | 0.062, 0.172, 1.03 | 0.054, 0.140, 0.99 |
No. of reflections | 5500 | 5499 | 5471 | 5439 |
No. of parameters | 390 | 418 | 409 | 395 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.14, −0.21 | 0.16, −0.22 | 0.19, −0.35 | 0.19, −0.26 |
| (rd48hlts) |
Crystal data |
Chemical formula | C22H24O6·C11H12O3 |
Mr | 576.62 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 8.3099 (12), 11.0026 (16), 17.471 (3) |
α, β, γ (°) | 99.768 (3), 91.912 (3), 110.392 (3) |
V (Å3) | 1468.1 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.45 × 0.24 × 0.14 |
|
Data collection |
Diffractometer | CCD area detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8381, 5409, 3394 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.606 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.116, 1.01 |
No. of reflections | 5409 |
No. of parameters | 397 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.18, −0.22 |
Hydrogen-bond geometry (Å, º) for (d6hlt_s) top
D—H···A | D—H | H···A | D···A | D—H···A |
O12A—H1A···O11Ai | 0.84 | 1.73 | 2.566 (3) | 170.4 |
O11B—H1B···O12Cii | 0.84 | 1.76 | 2.591 (2) | 167.7 |
O11C—H1C···O12Bii | 0.84 | 1.80 | 2.622 (3) | 166.0 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) for (d12hlt_s) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11A—H1A···O12Ai | 0.84 | 1.70 | 2.522 (5) | 166.4 |
O11B—H1B···O12Cii | 0.84 | 1.76 | 2.590 (3) | 169.8 |
O11C—H1C···O12Bii | 0.84 | 1.78 | 2.607 (4) | 168.2 |
O11E—H1E···O12Cii | 0.84 | 2.09 | 2.823 (6) | 145.9 |
O11C—H1C···O12Eii | 0.84 | 1.92 | 2.75 (2) | 168.9 |
O11D—H1D···O12Di | 0.84 | 2.33 | 3.094 (11) | 152.3 |
O11D—H1D···O12Ai | 0.84 | 2.18 | 2.929 (6) | 148.2 |
O11A—H1A···O12Di | 0.84 | 1.84 | 2.671 (6) | 169.0 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) for (rd24hlts) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11A—H1A···O12Ai | 0.84 | 1.63 | 2.429 (8) | 157.6 |
O11B—H1B···O12Cii | 0.84 | 1.70 | 2.522 (5) | 167.0 |
O11C—H1C···O12Bii | 0.84 | 1.77 | 2.603 (5) | 170.6 |
O11E—H1E···O12Cii | 0.84 | 1.87 | 2.686 (3) | 163.7 |
O11C—H1C···O12Eii | 0.84 | 1.85 | 2.685 (4) | 171.0 |
O11D—H1D···O12Di | 0.84 | 2.05 | 2.798 (5) | 148.4 |
O11D—H1D···O12Ai | 0.84 | 2.02 | 2.727 (5) | 141.2 |
O11A—H1A···O12Di | 0.84 | 1.63 | 2.453 (4) | 164.2 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) for (rd36hlts) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11A—H1A···O12Di | 0.84 | 1.66 | 2.472 (11) | 162.6 |
O11D—H1D···O12Ai | 0.84 | 2.02 | 2.702 (11) | 138.0 |
O11D—H1D···O12Di | 0.84 | 1.98 | 2.718 (3) | 145.6 |
O11C—H1C···O12Eii | 0.84 | 1.84 | 2.672 (2) | 172.0 |
O11E—H1E···O12Cii | 0.84 | 1.83 | 2.648 (2) | 163.0 |
O11C—H1C···O12Bii | 0.84 | 1.75 | 2.584 (12) | 171.9 |
O11B—H1B···O12Cii | 0.84 | 1.69 | 2.515 (12) | 166.8 |
O11A—H1A···O12Ai | 0.84 | 1.72 | 2.51 (2) | 155.5 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) for (rd48hlts) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11D—H1D···O12Di | 0.93 (2) | 1.80 (2) | 2.7139 (18) | 169 (2) |
O11C—H1C···O12Eii | 0.87 (2) | 1.79 (2) | 2.6616 (18) | 177 (2) |
O11E—H1E···O12Cii | 1.00 (3) | 1.65 (3) | 2.6350 (18) | 169 (2) |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z+1. |