Download citation
Download citation
link to html
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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768104007955/ws5010sup1.cif
Contains datablocks d6hlt_s, d12hlt_s, rd24hlts, rd36hlts, rd48hlts, global

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104007955/ws5010d6hlt_ssup2.fcf
Contains datablock d6hlt_s

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104007955/ws5010d12hlt_ssup3.fcf
Contains datablock d12hlt_s

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104007955/ws5010rd24hltssup4.fcf
Contains datablock rd24hlts

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104007955/ws5010rd36hltssup5.fcf
Contains datablock rd36hlts

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768104007955/ws5010rd48hltssup6.fcf
Contains datablock rd48hlts

CCDC references: 241458; 241459; 241460; 241461; 241462

Computing details top

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.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
(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 = 576.62F(000) = 612
Triclinic, P1Dx = 1.283 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 8.6452 (13) ÅCell parameters from 728 reflections
b = 10.8577 (17) Åθ = 2.4–26.3°
c = 17.262 (3) ŵ = 0.09 mm1
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 tubeRint = 0.022
Graphite monochromatorθmax = 25.5°, θmin = 1.2°
phi and ω scansh = 108
8177 measured reflectionsk = 1313
5500 independent reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H 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 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
0.124(C22H24O6)·2.752(C11H12O3)γ = 112.563 (3)°
Mr = 576.62V = 1492.4 (4) Å3
Triclinic, P1Z = 2
a = 8.6452 (13) ÅMo Kα radiation
b = 10.8577 (17) ŵ = 0.09 mm1
c = 17.262 (3) ÅT = 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 reflectionsRint = 0.022
5500 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.14 e Å3
5500 reflectionsΔρmin = 0.21 e Å3
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
xyzUiso*/UeqOcc. (<1)
C1A1.0162 (3)0.0296 (2)0.22157 (15)0.0409 (7)0.876 (2)
C2A1.0094 (4)0.0241 (3)0.30238 (15)0.0419 (7)0.876 (2)
C3A1.1499 (4)0.0338 (3)0.34793 (17)0.0495 (8)0.876 (2)
H3A1.14540.03180.40280.059*0.876 (2)
C4A1.2960 (4)0.0462 (3)0.31332 (19)0.0562 (8)0.876 (2)
H4A1.39160.05190.34450.067*0.876 (2)
C5A1.3042 (4)0.0504 (3)0.2336 (2)0.0578 (8)0.876 (2)
H5A1.40530.05950.21000.069*0.876 (2)
C6A1.1662 (4)0.0414 (3)0.18871 (17)0.0511 (8)0.876 (2)
H6A1.17250.04320.13390.061*0.876 (2)
C11A0.8669 (3)0.0204 (2)0.17418 (14)0.0431 (7)0.876 (2)
H11A0.77110.01400.20160.052*0.876 (2)
C12A0.8511 (4)0.0198 (2)0.09700 (14)0.0458 (7)0.876 (2)
H12A0.94490.02700.06780.055*0.876 (2)
C13A0.6963 (4)0.0087 (2)0.05566 (15)0.0453 (7)0.876 (2)
C21A0.8459 (4)0.0094 (3)0.41466 (14)0.0461 (7)0.876 (2)
H21C0.93380.08980.44120.055*0.876 (2)
H21D0.85920.07080.43380.055*0.876 (2)
C22A0.6753 (4)0.0064 (3)0.43047 (16)0.0522 (8)0.876 (2)
H22D0.66610.08860.41390.078*0.876 (2)
H22E0.65860.00050.48620.078*0.876 (2)
H22F0.58970.07090.40160.078*0.876 (2)
O11A0.6924 (2)0.01017 (19)0.01746 (11)0.0515 (6)0.876 (2)
O12A0.5693 (3)0.0032 (2)0.09562 (12)0.0584 (6)0.876 (2)
H1A0.48800.00830.06570.088*0.876 (2)
O21A0.8599 (3)0.0121 (2)0.33185 (10)0.0461 (5)0.876 (2)
C1B0.7885 (3)0.3467 (2)0.12841 (14)0.0335 (6)0.876 (2)
C2B0.7885 (3)0.3357 (2)0.04688 (14)0.0335 (6)0.876 (2)
C3B0.6507 (3)0.3319 (3)0.00137 (16)0.0429 (7)0.876 (2)
H3B0.65120.32460.05370.051*0.876 (2)
C4B0.5132 (4)0.3388 (3)0.03635 (18)0.0509 (8)0.876 (2)
H4B0.41880.33550.00510.061*0.876 (2)
C5B0.5107 (4)0.3504 (3)0.11661 (19)0.0505 (8)0.876 (2)
H5B0.41570.35550.14030.061*0.876 (2)
C6B0.6481 (3)0.3544 (3)0.16136 (15)0.0417 (7)0.876 (2)
H6B0.64670.36260.21630.050*0.876 (2)
C11B0.9351 (3)0.3525 (2)0.17578 (13)0.0362 (6)0.876 (2)
H11B1.03180.35910.14890.043*0.876 (2)
C12B0.9469 (3)0.3493 (2)0.25290 (13)0.0408 (7)0.876 (2)
H12B0.85210.34220.28140.049*0.876 (2)
C13B1.1002 (4)0.3566 (2)0.29525 (14)0.0403 (6)0.876 (2)
C21B0.9331 (3)0.3141 (3)0.06611 (13)0.0354 (6)0.876 (2)
H21E0.92630.39280.09060.043*0.876 (2)
H21F0.83720.23330.08710.043*0.876 (2)
C22B1.0954 (4)0.3014 (3)0.08263 (15)0.0448 (7)0.876 (2)
H22G1.18910.38470.06540.067*0.876 (2)
H22H1.09870.28370.13860.067*0.876 (2)
H22I1.10450.22750.05480.067*0.876 (2)
O11B1.0898 (2)0.34100 (19)0.36854 (10)0.0481 (5)0.876 (2)
H1B1.18270.34600.38800.072*0.876 (2)
O12B1.2329 (3)0.3776 (2)0.26032 (11)0.0467 (5)0.876 (2)
O21B0.9293 (2)0.32927 (19)0.01674 (10)0.0383 (5)0.876 (2)
C1C0.2212 (3)0.6717 (2)0.42538 (12)0.0383 (5)
C2C0.2336 (3)0.6865 (2)0.34524 (12)0.0387 (5)
C3C0.1000 (3)0.6899 (2)0.29955 (14)0.0519 (6)
H3C0.10960.70040.24540.062*
C4C0.0476 (3)0.6779 (3)0.33352 (15)0.0573 (7)
H4C0.13960.67910.30220.069*
C5C0.0623 (3)0.6642 (2)0.41232 (15)0.0536 (7)
H5C0.16360.65670.43520.064*
C6C0.0706 (3)0.6614 (2)0.45758 (13)0.0467 (6)
H6C0.06000.65220.51180.056*
C11C0.3617 (3)0.66488 (19)0.47177 (12)0.0386 (5)
H11C0.46010.67540.44540.046*
C12C0.3664 (3)0.6453 (2)0.54770 (12)0.0444 (6)
H12C0.27110.63590.57620.053*
C13C0.5136 (3)0.6378 (2)0.58787 (12)0.0430 (6)
C21C0.3994 (3)0.7040 (2)0.23407 (11)0.0406 (6)
H21A0.39360.78820.21710.049*
H21B0.30840.62790.20570.049*
C22C0.5668 (3)0.6999 (2)0.21845 (12)0.0456 (6)
H22A0.65510.77300.24910.068*
H22B0.58620.70990.16310.068*
H22C0.56860.61420.23300.068*
O11C0.49716 (19)0.61046 (16)0.65985 (8)0.0557 (5)
H1C0.58690.60810.67870.084*
O12C0.6474 (2)0.65866 (16)0.55414 (8)0.0515 (4)
O21C0.38280 (17)0.69618 (15)0.31622 (8)0.0435 (4)
C1D1.0226 (10)0.0482 (7)0.2390 (4)0.0386 (17)*0.124 (2)
C2D1.0064 (12)0.0102 (8)0.3149 (4)0.0386 (17)*0.124 (2)
C3D1.1339 (14)0.0175 (10)0.3546 (5)0.0386 (17)*0.124 (2)
H3D1.12080.04580.40620.046*0.124 (2)
C4D1.2788 (14)0.0024 (12)0.3171 (6)0.0386 (17)*0.124 (2)
H4D1.36620.01880.34390.046*0.124 (2)
C5D1.2986 (13)0.0354 (12)0.2424 (6)0.0386 (17)*0.124 (2)
H5D1.39760.04380.21700.046*0.124 (2)
C6D1.1710 (11)0.0613 (9)0.2043 (5)0.0386 (17)*0.124 (2)
H6D1.18530.08900.15260.046*0.124 (2)
C11D0.8902 (8)0.0913 (5)0.2057 (4)0.0386 (17)*0.124 (2)
H11D0.77630.02480.21590.046*0.124 (2)
C12D0.8950 (8)0.1272 (6)0.1203 (3)0.0386 (17)*0.124 (2)
H12D0.99670.12560.09520.046*0.124 (2)
C13D0.7324 (10)0.0497 (7)0.0709 (4)0.0386 (17)*0.124 (2)
C21D0.8448 (16)0.0161 (12)0.4273 (5)0.0386 (17)*0.124 (2)
H21G0.93830.05680.45660.046*0.124 (2)
H21H0.84960.10240.44040.046*0.124 (2)
C22D0.6783 (16)0.0116 (15)0.4483 (5)0.0386 (17)*0.124 (2)
H22J0.66550.02190.50410.058*0.124 (2)
H22K0.58670.08430.41910.058*0.124 (2)
H22L0.67500.07440.43520.058*0.124 (2)
O11D0.7562 (13)0.0444 (9)0.0043 (4)0.0386 (17)*0.124 (2)
H11E0.66410.00120.02890.058*0.124 (2)
O12D0.5934 (9)0.0114 (8)0.0960 (5)0.0386 (17)*0.124 (2)
O21D0.8584 (12)0.0007 (9)0.3461 (4)0.0386 (17)*0.124 (2)
C1E0.7828 (11)0.3225 (7)0.1120 (5)0.0386 (17)*0.124 (2)
C2E0.7926 (13)0.3444 (8)0.0336 (5)0.0386 (17)*0.124 (2)
C3E0.6643 (15)0.3668 (11)0.0075 (6)0.0386 (17)*0.124 (2)
H3E0.67120.38170.06130.046*0.124 (2)
C4E0.5264 (15)0.3669 (13)0.0317 (7)0.0386 (17)*0.124 (2)
H4E0.43880.38200.00410.046*0.124 (2)
C5E0.5146 (14)0.3458 (13)0.1091 (7)0.0386 (17)*0.124 (2)
H5E0.42030.34680.13530.046*0.124 (2)
C6E0.6424 (12)0.3228 (10)0.1488 (5)0.0386 (17)*0.124 (2)
H6E0.63380.30680.20250.046*0.124 (2)
C11E0.9126 (9)0.2761 (6)0.1467 (4)0.0386 (17)*0.124 (2)
H11F1.02770.34120.13700.046*0.124 (2)
C12E0.9055 (9)0.2403 (6)0.2322 (4)0.0386 (17)*0.124 (2)
H12E0.80230.24080.25620.046*0.124 (2)
C13E1.0645 (11)0.3168 (7)0.2831 (4)0.0386 (17)*0.124 (2)
C21E0.9380 (16)0.3355 (12)0.0822 (4)0.0386 (17)*0.124 (2)
H21I0.93740.41850.10350.046*0.124 (2)
H21J0.83740.25940.10420.046*0.124 (2)
C22E1.0965 (16)0.3150 (15)0.1027 (5)0.0386 (17)*0.124 (2)
H22M1.10110.30840.15930.058*0.124 (2)
H22N1.09540.23250.08130.058*0.124 (2)
H22O1.19500.39100.08060.058*0.124 (2)
O11E1.0396 (14)0.3063 (9)0.3571 (4)0.0386 (17)*0.124 (2)
H11G1.12990.34970.38300.058*0.124 (2)
O12E1.2033 (10)0.3675 (7)0.2571 (5)0.0386 (17)*0.124 (2)
O21E0.9371 (13)0.3445 (9)0.0012 (4)0.0386 (17)*0.124 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0517 (17)0.0311 (14)0.0388 (16)0.0136 (13)0.0141 (13)0.0042 (11)
C2A0.0439 (17)0.0392 (15)0.0404 (17)0.0132 (13)0.0096 (13)0.0004 (12)
C3A0.0512 (19)0.0520 (19)0.0458 (17)0.0199 (16)0.0086 (14)0.0015 (14)
C4A0.0473 (19)0.054 (2)0.068 (2)0.0208 (16)0.0072 (15)0.0002 (16)
C5A0.053 (2)0.0555 (19)0.069 (2)0.0239 (16)0.0231 (16)0.0051 (16)
C6A0.065 (2)0.0455 (17)0.0446 (18)0.0222 (15)0.0219 (15)0.0031 (13)
C11A0.0577 (18)0.0315 (14)0.0387 (16)0.0146 (13)0.0153 (13)0.0028 (11)
C12A0.0614 (19)0.0382 (15)0.0389 (16)0.0193 (14)0.0142 (13)0.0051 (12)
C13A0.065 (2)0.0314 (15)0.0370 (17)0.0148 (14)0.0128 (14)0.0042 (12)
C21A0.0558 (18)0.0586 (19)0.0285 (16)0.0268 (15)0.0062 (12)0.0016 (12)
C22A0.0528 (18)0.069 (2)0.0363 (17)0.0246 (16)0.0078 (13)0.0028 (14)
O11A0.0632 (14)0.0536 (13)0.0315 (11)0.0145 (11)0.0119 (9)0.0058 (8)
O12A0.0741 (15)0.0621 (14)0.0405 (12)0.0258 (11)0.0200 (11)0.0091 (9)
O21A0.0435 (11)0.0631 (12)0.0301 (11)0.0187 (9)0.0065 (8)0.0013 (8)
C1B0.0376 (15)0.0333 (14)0.0308 (14)0.0146 (12)0.0040 (11)0.0036 (10)
C2B0.0347 (15)0.0327 (14)0.0339 (15)0.0134 (11)0.0047 (11)0.0035 (10)
C3B0.0403 (16)0.0552 (19)0.0349 (15)0.0209 (15)0.0031 (12)0.0022 (12)
C4B0.0364 (17)0.067 (2)0.0522 (19)0.0226 (16)0.0010 (13)0.0041 (15)
C5B0.0437 (17)0.0582 (18)0.0563 (19)0.0261 (14)0.0139 (14)0.0036 (14)
C6B0.0456 (17)0.0462 (17)0.0349 (15)0.0188 (14)0.0090 (12)0.0033 (12)
C11B0.0464 (16)0.0321 (14)0.0291 (14)0.0136 (12)0.0059 (11)0.0044 (10)
C12B0.0489 (17)0.0446 (16)0.0298 (15)0.0188 (13)0.0041 (12)0.0022 (11)
C13B0.0595 (19)0.0349 (15)0.0288 (14)0.0202 (14)0.0059 (13)0.0043 (11)
C21B0.0369 (15)0.0435 (16)0.0246 (14)0.0140 (12)0.0024 (10)0.0017 (11)
C22B0.0479 (17)0.0572 (18)0.0341 (16)0.0249 (14)0.0089 (13)0.0044 (13)
O11B0.0549 (14)0.0664 (13)0.0278 (10)0.0282 (11)0.0041 (8)0.0055 (9)
O12B0.0518 (13)0.0585 (12)0.0290 (10)0.0190 (10)0.0096 (9)0.0092 (8)
O21B0.0377 (10)0.0567 (12)0.0246 (10)0.0226 (9)0.0037 (8)0.0023 (8)
C1C0.0407 (14)0.0386 (13)0.0344 (13)0.0136 (11)0.0082 (10)0.0003 (10)
C2C0.0339 (13)0.0437 (14)0.0367 (13)0.0131 (11)0.0045 (10)0.0010 (10)
C3C0.0440 (15)0.0720 (17)0.0411 (14)0.0241 (13)0.0036 (11)0.0029 (12)
C4C0.0409 (15)0.0758 (19)0.0599 (18)0.0278 (14)0.0044 (12)0.0022 (14)
C5C0.0447 (16)0.0603 (17)0.0607 (17)0.0243 (13)0.0187 (13)0.0053 (13)
C6C0.0515 (16)0.0478 (14)0.0418 (14)0.0189 (12)0.0153 (12)0.0049 (11)
C11C0.0436 (14)0.0365 (13)0.0343 (13)0.0136 (11)0.0079 (10)0.0021 (9)
C12C0.0514 (15)0.0490 (14)0.0334 (13)0.0189 (12)0.0123 (11)0.0060 (10)
C13C0.0612 (17)0.0415 (13)0.0255 (12)0.0190 (12)0.0049 (11)0.0016 (10)
C21C0.0405 (14)0.0543 (14)0.0280 (12)0.0190 (11)0.0028 (9)0.0048 (10)
C22C0.0437 (14)0.0591 (15)0.0355 (13)0.0207 (12)0.0070 (10)0.0048 (11)
O11C0.0534 (11)0.0795 (12)0.0327 (9)0.0229 (9)0.0045 (7)0.0121 (8)
O12C0.0570 (11)0.0668 (11)0.0339 (9)0.0264 (9)0.0128 (8)0.0037 (7)
O21C0.0369 (9)0.0689 (11)0.0267 (8)0.0227 (8)0.0026 (6)0.0021 (7)
Geometric parameters (Å, º) top
C1A—C6A1.397 (4)C12C—C13C1.458 (3)
C1A—C2A1.401 (3)C12C—H12C0.9500
C1A—C11A1.470 (4)C13C—O12C1.260 (3)
C2A—O21A1.368 (3)C13C—O11C1.290 (2)
C2A—C3A1.389 (4)C21C—O21C1.433 (2)
C3A—C4A1.379 (4)C21C—C22C1.499 (3)
C3A—H3A0.9500C21C—H21A0.9900
C4A—C5A1.383 (4)C21C—H21B0.9900
C4A—H4A0.9500C22C—H22A0.9800
C5A—C6A1.366 (4)C22C—H22B0.9800
C5A—H5A0.9500C22C—H22C0.9800
C6A—H6A0.9500O11C—H1C0.8400
C11A—C12A1.334 (3)C1D—C2D1.3866
C11A—H11A0.9500C1D—C6D1.3961
C12A—C13A1.454 (4)C1D—C11D1.4979
C12A—H12A0.9500C2D—O21D1.3716
C13A—O11A1.262 (3)C2D—C3D1.4116
C13A—O12A1.285 (3)C3D—C4D1.3884
C21A—O21A1.440 (3)C3D—H3D0.9500
C21A—C22A1.497 (3)C4D—C5D1.3674
C21A—H21C0.9900C4D—H4D0.9500
C21A—H21D0.9900C5D—C6D1.3890
C22A—H22D0.9800C5D—H5D0.9500
C22A—H22E0.9800C6D—H6D0.9500
C22A—H22F0.9800C11D—C12D1.5394
O12A—H1A0.8400C11D—C12E1.6166
C1B—C6B1.389 (3)C11D—H11D1.0000
C1B—C2B1.407 (3)C12D—C13D1.5337
C1B—C11B1.462 (3)C12D—C11E1.6084
C2B—O21B1.366 (3)C12D—H12D1.0000
C2B—C3B1.389 (3)C13D—O12D1.2148
C3B—C4B1.379 (3)C13D—O11D1.3234
C3B—H3B0.9500C21D—O21D1.4229
C4B—C5B1.387 (4)C21D—C22D1.5151
C4B—H4B0.9500C21D—H21G0.9900
C5B—C6B1.378 (4)C21D—H21H0.9900
C5B—H5B0.9500C22D—H22J0.9800
C6B—H6B0.9500C22D—H22K0.9800
C11B—C12B1.334 (3)C22D—H22L0.9800
C11B—H11B0.9500O11D—H11E0.8400
C12B—C13B1.463 (3)C1E—C2E1.3829
C12B—H12B0.9500C1E—C6E1.3919
C13B—O12B1.262 (3)C1E—C11E1.5118
C13B—O11B1.285 (3)C2E—O21E1.3878
C21B—O21B1.436 (3)C2E—C3E1.3985
C21B—C22B1.497 (3)C3E—C4E1.3933
C21B—H21E0.9900C3E—H3E0.9500
C21B—H21F0.9900C4E—C5E1.3664
C22B—H22G0.9800C4E—H4E0.9500
C22B—H22H0.9800C5E—C6E1.3865
C22B—H22I0.9800C5E—H5E0.9500
O11B—H1B0.8400C6E—H6E0.9500
C1C—C6C1.401 (3)C11E—C12E1.5393
C1C—C2C1.403 (3)C11E—H11F1.0000
C1C—C11C1.458 (3)C12E—C13E1.5245
C2C—O21C1.369 (2)C12E—H12E1.0000
C2C—C3C1.388 (3)C13E—O12E1.2245
C3C—C4C1.387 (3)C13E—O11E1.3047
C3C—H3C0.9500C21E—O21E1.4391
C4C—C5C1.380 (3)C21E—C22E1.5213
C4C—H4C0.9500C21E—H21I0.9900
C5C—C6C1.377 (3)C21E—H21J0.9900
C5C—H5C0.9500C22E—H22M0.9800
C6C—H6C0.9500C22E—H22N0.9800
C11C—C12C1.339 (3)C22E—H22O0.9800
C11C—H11C0.9500O11E—H11G0.8400
C6A—C1A—C2A118.0 (3)O21C—C21C—C22C106.68 (16)
C6A—C1A—C11A122.2 (2)O21C—C21C—H21A110.4
C2A—C1A—C11A119.7 (2)C22C—C21C—H21A110.4
O21A—C2A—C3A123.7 (2)O21C—C21C—H21B110.4
O21A—C2A—C1A115.9 (2)C22C—C21C—H21B110.4
C3A—C2A—C1A120.4 (3)H21A—C21C—H21B108.6
C4A—C3A—C2A119.8 (3)C21C—C22C—H22A109.5
C4A—C3A—H3A120.1C21C—C22C—H22B109.5
C2A—C3A—H3A120.1H22A—C22C—H22B109.5
C3A—C4A—C5A120.5 (3)C21C—C22C—H22C109.5
C3A—C4A—H4A119.8H22A—C22C—H22C109.5
C5A—C4A—H4A119.8H22B—C22C—H22C109.5
C6A—C5A—C4A119.8 (3)C13C—O11C—H1C109.5
C6A—C5A—H5A120.1C2C—O21C—C21C118.45 (15)
C4A—C5A—H5A120.1C2D—C1D—C6D117.6
C5A—C6A—C1A121.5 (3)C2D—C1D—C11D116.5
C5A—C6A—H6A119.2C6D—C1D—C11D125.3
C1A—C6A—H6A119.2O21D—C2D—C1D115.0
C12A—C11A—C1A127.2 (3)O21D—C2D—C3D124.0
C12A—C11A—H11A116.4C1D—C2D—C3D121.0
C1A—C11A—H11A116.4C4D—C3D—C2D118.8
C11A—C12A—C13A122.7 (3)C4D—C3D—H3D120.6
C11A—C12A—H12A118.6C2D—C3D—H3D120.6
C13A—C12A—H12A118.6C5D—C4D—C3D121.6
O11A—C13A—O12A123.2 (3)C5D—C4D—H4D119.2
O11A—C13A—C12A118.7 (2)C3D—C4D—H4D119.2
O12A—C13A—C12A118.1 (2)C4D—C5D—C6D118.6
O21A—C21A—C22A107.1 (2)C4D—C5D—H5D120.7
O21A—C21A—H21C110.3C6D—C5D—H5D120.7
C22A—C21A—H21C110.3C5D—C6D—C1D122.5
O21A—C21A—H21D110.3C5D—C6D—H6D118.7
C22A—C21A—H21D110.3C1D—C6D—H6D118.7
H21C—C21A—H21D108.6C1D—C11D—C12D119.2
C21A—C22A—H22D109.5C1D—C11D—C12E116.5
C21A—C22A—H22E109.5C12D—C11D—C12E89.6
H22D—C22A—H22E109.5C1D—C11D—H11D110.0
C21A—C22A—H22F109.5C12D—C11D—H11D110.0
H22D—C22A—H22F109.5C12E—C11D—H11D110.0
H22E—C22A—H22F109.5C13D—C12D—C11D114.6
C13A—O12A—H1A109.5C13D—C12D—C11E112.4
C2A—O21A—C21A118.73 (19)C11D—C12D—C11E90.4
C6B—C1B—C2B118.1 (2)C13D—C12D—H12D112.6
C6B—C1B—C11B122.0 (2)C11D—C12D—H12D112.6
C2B—C1B—C11B119.9 (2)C11E—C12D—H12D112.6
O21B—C2B—C3B123.3 (2)O12D—C13D—O11D122.4
O21B—C2B—C1B116.3 (2)O12D—C13D—C12D124.0
C3B—C2B—C1B120.4 (2)O11D—C13D—C12D113.0
C4B—C3B—C2B119.7 (2)O21D—C21D—C22D107.7
C4B—C3B—H3B120.1O21D—C21D—H21G110.2
C2B—C3B—H3B120.1C22D—C21D—H21G110.2
C3B—C4B—C5B120.9 (2)O21D—C21D—H21H110.2
C3B—C4B—H4B119.5C22D—C21D—H21H110.2
C5B—C4B—H4B119.5H21G—C21D—H21H108.5
C6B—C5B—C4B119.0 (2)C21D—C22D—H22J109.5
C6B—C5B—H5B120.5C21D—C22D—H22K109.5
C4B—C5B—H5B120.5H22J—C22D—H22K109.5
C5B—C6B—C1B121.9 (2)C21D—C22D—H22L109.5
C5B—C6B—H6B119.1H22J—C22D—H22L109.5
C1B—C6B—H6B119.1H22K—C22D—H22L109.5
C12B—C11B—C1B126.5 (2)C13D—O11D—H11E109.5
C12B—C11B—H11B116.7C2D—O21D—C21D118.0
C1B—C11B—H11B116.7C2E—C1E—C6E118.5
C11B—C12B—C13B122.5 (2)C2E—C1E—C11E115.6
C11B—C12B—H12B118.8C6E—C1E—C11E124.9
C13B—C12B—H12B118.8C1E—C2E—O21E115.2
O12B—C13B—O11B123.4 (2)C1E—C2E—C3E120.7
O12B—C13B—C12B120.6 (2)O21E—C2E—C3E124.1
O11B—C13B—C12B115.9 (2)C4E—C3E—C2E119.0
O21B—C21B—C22B107.09 (18)C4E—C3E—H3E120.5
O21B—C21B—H21E110.3C2E—C3E—H3E120.5
C22B—C21B—H21E110.3C5E—C4E—C3E121.3
O21B—C21B—H21F110.3C5E—C4E—H4E119.4
C22B—C21B—H21F110.3C3E—C4E—H4E119.4
H21E—C21B—H21F108.6C4E—C5E—C6E119.0
C21B—C22B—H22G109.5C4E—C5E—H5E120.5
C21B—C22B—H22H109.5C6E—C5E—H5E120.5
H22G—C22B—H22H109.5C5E—C6E—C1E121.6
C21B—C22B—H22I109.5C5E—C6E—H6E119.2
H22G—C22B—H22I109.5C1E—C6E—H6E119.2
H22H—C22B—H22I109.5C1E—C11E—C12E119.6
C13B—O11B—H1B109.5C1E—C11E—C12D116.7
C2B—O21B—C21B118.34 (17)C12E—C11E—C12D89.9
C6C—C1C—C2C117.9 (2)C1E—C11E—H11F109.7
C6C—C1C—C11C122.4 (2)C12E—C11E—H11F109.7
C2C—C1C—C11C119.69 (19)C12D—C11E—H11F109.7
O21C—C2C—C3C123.3 (2)C13E—C12E—C11E115.4
O21C—C2C—C1C115.99 (18)C13E—C12E—C11D112.1
C3C—C2C—C1C120.8 (2)C11E—C12E—C11D90.1
C2C—C3C—C4C119.6 (2)C13E—C12E—H12E112.5
C2C—C3C—H3C120.2C11E—C12E—H12E112.5
C4C—C3C—H3C120.2C11D—C12E—H12E112.5
C5C—C4C—C3C120.7 (2)O12E—C13E—O11E123.8
C5C—C4C—H4C119.6O12E—C13E—C12E123.0
C3C—C4C—H4C119.6O11E—C13E—C12E112.5
C6C—C5C—C4C119.6 (2)O21E—C21E—C22E107.3
C6C—C5C—H5C120.2O21E—C21E—H21I110.3
C4C—C5C—H5C120.2C22E—C21E—H21I110.3
C5C—C6C—C1C121.4 (2)O21E—C21E—H21J110.3
C5C—C6C—H6C119.3C22E—C21E—H21J110.3
C1C—C6C—H6C119.3H21I—C21E—H21J108.5
C12C—C11C—C1C126.7 (2)C21E—C22E—H22M109.5
C12C—C11C—H11C116.6C21E—C22E—H22N109.5
C1C—C11C—H11C116.6H22M—C22E—H22N109.5
C11C—C12C—C13C121.9 (2)C21E—C22E—H22O109.5
C11C—C12C—H12C119.0H22M—C22E—H22O109.5
C13C—C12C—H12C119.0H22N—C22E—H22O109.5
O12C—C13C—O11C123.0 (2)C13E—O11E—H11G109.5
O12C—C13C—C12C121.7 (2)C2E—O21E—C21E117.6
O11C—C13C—C12C115.3 (2)
C6A—C1A—C2A—O21A179.7 (2)C6D—C1D—C2D—C3D1.6
C11A—C1A—C2A—O21A1.0 (3)C11D—C1D—C2D—C3D172.7
C6A—C1A—C2A—C3A1.7 (4)O21D—C2D—C3D—C4D179.8
C11A—C1A—C2A—C3A179.5 (2)C1D—C2D—C3D—C4D1.7
O21A—C2A—C3A—C4A179.7 (2)C2D—C3D—C4D—C5D1.5
C1A—C2A—C3A—C4A1.3 (4)C3D—C4D—C5D—C6D1.1
C2A—C3A—C4A—C5A0.6 (4)C4D—C5D—C6D—C1D1.0
C3A—C4A—C5A—C6A0.4 (4)C2D—C1D—C6D—C5D1.3
C4A—C5A—C6A—C1A0.8 (4)C11D—C1D—C6D—C5D171.5
C2A—C1A—C6A—C5A1.5 (4)C2D—C1D—C11D—C12D176.6
C11A—C1A—C6A—C5A179.8 (2)C6D—C1D—C11D—C12D13.1
C6A—C1A—C11A—C12A1.0 (4)C2D—C1D—C11D—C12E77.8
C2A—C1A—C11A—C12A177.8 (2)C6D—C1D—C11D—C12E92.6
C1A—C11A—C12A—C13A179.3 (2)C1D—C11D—C12D—C13D125.2
C11A—C12A—C13A—O11A179.4 (2)C12E—C11D—C12D—C13D114.3
C11A—C12A—C13A—O12A1.2 (4)C1D—C11D—C12D—C11E119.8
C3A—C2A—O21A—C21A0.1 (4)C12E—C11D—C12D—C11E0.7
C1A—C2A—O21A—C21A178.4 (2)C11D—C12D—C13D—O12D31.8
C22A—C21A—O21A—C2A175.7 (2)C11E—C12D—C13D—O12D69.5
C6B—C1B—C2B—O21B179.6 (2)C11D—C12D—C13D—O11D157.0
C11B—C1B—C2B—O21B0.8 (3)C11E—C12D—C13D—O11D101.6
C6B—C1B—C2B—C3B0.4 (3)C1D—C2D—O21D—C21D169.1
C11B—C1B—C2B—C3B179.2 (2)C3D—C2D—O21D—C21D12.3
O21B—C2B—C3B—C4B179.9 (2)C22D—C21D—O21D—C2D174.3
C1B—C2B—C3B—C4B0.1 (4)C6E—C1E—C2E—O21E179.2
C2B—C3B—C4B—C5B0.5 (4)C11E—C1E—C2E—O21E11.3
C3B—C4B—C5B—C6B0.3 (4)C6E—C1E—C2E—C3E0.2
C4B—C5B—C6B—C1B0.2 (4)C11E—C1E—C2E—C3E169.8
C2B—C1B—C6B—C5B0.6 (4)C1E—C2E—C3E—C4E0.1
C11B—C1B—C6B—C5B179.3 (2)O21E—C2E—C3E—C4E178.7
C6B—C1B—C11B—C12B8.5 (4)C2E—C3E—C4E—C5E0.0
C2B—C1B—C11B—C12B172.8 (2)C3E—C4E—C5E—C6E0.5
C1B—C11B—C12B—C13B179.6 (2)C4E—C5E—C6E—C1E0.9
C11B—C12B—C13B—O12B6.0 (4)C2E—C1E—C6E—C5E0.7
C11B—C12B—C13B—O11B174.2 (2)C11E—C1E—C6E—C5E169.2
C3B—C2B—O21B—C21B1.8 (3)C2E—C1E—C11E—C12E176.1
C1B—C2B—O21B—C21B178.21 (19)C6E—C1E—C11E—C12E7.4
C22B—C21B—O21B—C2B176.56 (19)C2E—C1E—C11E—C12D69.7
C6C—C1C—C2C—O21C179.96 (19)C6E—C1E—C11E—C12D99.1
C11C—C1C—C2C—O21C1.2 (3)C13D—C12D—C11E—C1E7.3
C6C—C1C—C2C—C3C0.4 (3)C11D—C12D—C11E—C1E124.2
C11C—C1C—C2C—C3C178.4 (2)C13D—C12D—C11E—C12E116.2
O21C—C2C—C3C—C4C179.3 (2)C11D—C12D—C11E—C12E0.7
C1C—C2C—C3C—C4C0.3 (3)C1E—C11E—C12E—C13E123.6
C2C—C3C—C4C—C5C0.7 (4)C12D—C11E—C12E—C13E115.4
C3C—C4C—C5C—C6C0.5 (4)C1E—C11E—C12E—C11D121.7
C4C—C5C—C6C—C1C0.2 (4)C12D—C11E—C12E—C11D0.7
C2C—C1C—C6C—C5C0.6 (3)C1D—C11D—C12E—C13E4.5
C11C—C1C—C6C—C5C178.1 (2)C12D—C11D—C12E—C13E118.3
C6C—C1C—C11C—C12C1.7 (3)C1D—C11D—C12E—C11E122.1
C2C—C1C—C11C—C12C176.9 (2)C12D—C11D—C12E—C11E0.7
C1C—C11C—C12C—C13C178.88 (19)C11E—C12E—C13E—O12E23.8
C11C—C12C—C13C—O12C4.9 (3)C11D—C12E—C13E—O12E77.5
C11C—C12C—C13C—O11C175.92 (19)C11E—C12E—C13E—O11E165.0
C3C—C2C—O21C—C21C3.0 (3)C11D—C12E—C13E—O11E93.7
C1C—C2C—O21C—C21C176.63 (17)C1E—C2E—O21E—C21E165.9
C22C—C21C—O21C—C2C174.50 (18)C3E—C2E—O21E—C21E15.2
C6D—C1D—C2D—O21D179.8C22E—C21E—O21E—C2E171.1
C11D—C1D—C2D—O21D8.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12A—H1A···O11Ai0.841.732.566 (3)170
O11B—H1B···O12Cii0.841.762.591 (2)168
O11C—H1C···O12Bii0.841.802.622 (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 = 576.62F(000) = 612
Triclinic, P1Dx = 1.285 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 8.6164 (10) ÅCell parameters from 923 reflections
b = 10.8765 (14) Åθ = 2.4–24.1°
c = 17.292 (2) ŵ = 0.09 mm1
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 tubeRint = 0.023
Graphite monochromatorθmax = 25.5°, θmin = 1.2°
phi and ω scansh = 1010
8551 measured reflectionsk = 138
5499 independent reflectionsl = 2018
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H 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 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
0.219(C22H24O6)·2.562(C11H12O3)γ = 112.657 (3)°
Mr = 576.62V = 1490.4 (3) Å3
Triclinic, P1Z = 2
a = 8.6164 (10) ÅMo Kα radiation
b = 10.8765 (14) ŵ = 0.09 mm1
c = 17.292 (2) ÅT = 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 reflectionsRint = 0.023
5499 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.16 e Å3
5499 reflectionsΔρmin = 0.22 e Å3
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
xyzUiso*/UeqOcc. (<1)
C1A1.0120 (5)0.0257 (4)0.2201 (3)0.0485 (14)0.781 (3)
C2A1.0060 (5)0.0216 (4)0.3008 (3)0.0487 (19)0.781 (3)
C3A1.1473 (5)0.0300 (5)0.3463 (2)0.0545 (10)0.781 (3)
H3A1.14290.02860.40100.065*0.781 (3)
C4A1.2926 (5)0.0402 (6)0.3120 (2)0.0603 (12)0.781 (3)
H4A1.38770.04340.34280.072*0.781 (3)
C5A1.3004 (5)0.0457 (5)0.2317 (3)0.061 (3)0.781 (3)
H5A1.40150.05470.20780.073*0.781 (3)
C6A1.1619 (5)0.0381 (5)0.1877 (3)0.0549 (18)0.781 (3)
H6A1.16840.04150.13300.066*0.781 (3)
C11A0.8621 (4)0.0171 (3)0.17306 (17)0.0459 (8)0.781 (3)
H11A0.76610.01120.20050.055*0.781 (3)
C12A0.8464 (4)0.0167 (3)0.09625 (17)0.0525 (9)0.781 (3)
H12A0.94030.02340.06700.063*0.781 (3)
C13A0.6903 (5)0.0065 (4)0.0553 (2)0.0505 (9)0.781 (3)
C21A0.8434 (4)0.0065 (5)0.4142 (2)0.0492 (14)0.781 (3)
H21A0.93260.08630.44130.059*0.781 (3)
H21B0.85510.07430.43250.059*0.781 (3)
C22A0.6728 (5)0.0050 (4)0.4295 (3)0.0532 (13)0.781 (3)
H22A0.66390.08630.41200.080*0.781 (3)
H22B0.65660.00110.48530.080*0.781 (3)
H22C0.58610.07350.40140.080*0.781 (3)
O11A0.6944 (5)0.0094 (3)0.01777 (15)0.0577 (7)0.781 (3)
H1A0.60010.00250.03680.087*0.781 (3)
O12A0.5639 (5)0.0046 (4)0.09329 (16)0.0634 (17)0.781 (3)
O21A0.8568 (3)0.0095 (3)0.3309 (2)0.0523 (13)0.781 (3)
C1B0.7815 (4)0.3434 (5)0.1263 (3)0.0394 (15)0.781 (3)
C2B0.7819 (4)0.3338 (4)0.0445 (3)0.038 (2)0.781 (3)
C3B0.6445 (4)0.3311 (6)0.00049 (18)0.0452 (12)0.781 (3)
H3B0.64490.32380.05550.054*0.781 (3)
C4B0.5077 (5)0.3391 (6)0.03439 (19)0.0498 (16)0.781 (3)
H4B0.41420.33820.00330.060*0.781 (3)
C5B0.5044 (7)0.3483 (4)0.1145 (2)0.054 (6)0.781 (3)
H5B0.40860.35220.13830.064*0.781 (3)
C6B0.6407 (4)0.3516 (6)0.1592 (2)0.0461 (15)0.781 (3)
H6B0.63880.35970.21410.055*0.781 (3)
C11B0.9283 (3)0.3489 (3)0.17385 (15)0.0379 (7)0.781 (3)
H11B1.02540.35530.14720.045*0.781 (3)
C12B0.9393 (4)0.3458 (3)0.25109 (15)0.0427 (8)0.781 (3)
H12B0.84410.33810.27960.051*0.781 (3)
C13B1.0935 (5)0.3538 (5)0.2928 (2)0.0446 (11)0.781 (3)
C21B0.9269 (4)0.3128 (5)0.0685 (2)0.0385 (13)0.781 (3)
H21C0.92160.39230.09190.046*0.781 (3)
H21D0.82980.23280.09030.046*0.781 (3)
C22B1.0888 (4)0.2989 (5)0.0853 (3)0.0505 (14)0.781 (3)
H22D1.18380.38050.06560.076*0.781 (3)
H22E1.09380.28470.14140.076*0.781 (3)
H22F1.09480.22250.05980.076*0.781 (3)
O11B1.0788 (5)0.3355 (4)0.36527 (13)0.0470 (9)0.781 (3)
H1B1.17120.34040.38560.071*0.781 (3)
O12B1.2268 (5)0.3746 (3)0.25858 (16)0.0560 (16)0.781 (3)
O21B0.9229 (3)0.3270 (3)0.01446 (18)0.0421 (11)0.781 (3)
C1C0.2262 (3)0.6688 (2)0.42763 (12)0.0392 (5)
C2C0.2372 (3)0.6803 (2)0.34742 (12)0.0412 (6)
C3C0.1009 (3)0.6809 (3)0.30212 (14)0.0569 (7)
H3C0.10870.68880.24780.068*
C4C0.0454 (3)0.6700 (3)0.33638 (15)0.0628 (8)
H4C0.13860.66950.30510.075*
C5C0.0589 (3)0.6598 (3)0.41498 (15)0.0588 (7)
H5C0.16000.65330.43800.071*
C6C0.0753 (3)0.6591 (2)0.45989 (13)0.0492 (6)
H6C0.06570.65180.51420.059*
C11C0.3684 (3)0.6644 (2)0.47435 (12)0.0399 (6)
H11C0.46730.67500.44810.048*
C12C0.3736 (3)0.6471 (2)0.54975 (12)0.0463 (6)
H12C0.27790.63840.57810.056*
C13C0.5223 (3)0.6409 (2)0.59071 (12)0.0447 (6)
C21C0.4027 (3)0.6984 (2)0.23604 (11)0.0422 (6)
H21E0.39450.78170.21980.051*
H21F0.31240.62140.20730.051*
C22C0.5723 (3)0.6975 (2)0.21985 (12)0.0462 (6)
H22G0.65990.77040.25150.069*
H22H0.59190.70950.16480.069*
H22I0.57580.61190.23270.069*
O11C0.50424 (19)0.61456 (17)0.66263 (8)0.0582 (5)
H1C0.59440.61380.68220.087*
O12C0.6561 (2)0.66056 (16)0.55754 (8)0.0538 (5)
O21C0.38640 (17)0.69009 (16)0.31813 (8)0.0452 (4)
C1D1.0212 (6)0.0474 (5)0.2369 (3)0.032 (6)*0.219 (3)
C2D1.0063 (8)0.0097 (6)0.3125 (3)0.030 (6)*0.219 (3)
C3D1.1344 (10)0.0185 (7)0.3512 (4)0.044 (5)*0.219 (3)
H3D1.12210.04670.40250.053*0.219 (3)
C4D1.2787 (10)0.0043 (9)0.3130 (5)0.066 (8)*0.219 (3)
H4D1.36650.02110.33910.079*0.219 (3)
C5D1.2973 (9)0.0332 (9)0.2386 (4)0.050 (10)*0.219 (3)
H5D1.39590.04100.21280.061*0.219 (3)
C6D1.1691 (7)0.0597 (7)0.2015 (3)0.058 (9)*0.219 (3)
H6D1.18260.08720.15010.069*0.219 (3)
C11D0.8885 (5)0.0911 (4)0.2049 (2)0.034 (3)*0.219 (3)
H11D0.77420.02510.21520.040*0.219 (3)
C12D0.8918 (5)0.1267 (4)0.1198 (2)0.033 (2)*0.219 (3)
H12D0.99310.12460.09420.039*0.219 (3)
C13D0.7274 (6)0.0497 (5)0.0708 (3)0.033 (4)*0.219 (3)
C21D0.8467 (11)0.0154 (9)0.4255 (3)0.063 (8)*0.219 (3)
H21G0.94160.05730.45480.076*0.219 (3)
H21H0.85090.10190.43780.076*0.219 (3)
C22D0.6806 (12)0.0100 (11)0.4475 (3)0.048 (6)*0.219 (3)
H22J0.66890.02010.50320.073*0.219 (3)
H22K0.58760.08250.41830.073*0.219 (3)
H22L0.67790.07610.43530.073*0.219 (3)
O11D0.7495 (9)0.0441 (6)0.0045 (2)0.056 (4)*0.219 (3)
H1D0.65640.00110.02880.085*0.219 (3)
O12D0.5885 (6)0.0121 (6)0.0963 (3)0.048 (6)*0.219 (3)
O21D0.8587 (8)0.0004 (6)0.3444 (3)0.037 (5)*0.219 (3)
C1E0.7815 (7)0.3231 (5)0.1140 (3)0.039 (7)*0.219 (3)
C2E0.7898 (9)0.3447 (6)0.0359 (3)0.029 (8)*0.219 (3)
C3E0.6609 (10)0.3676 (8)0.0042 (4)0.056 (8)*0.219 (3)
H3E0.66680.38220.05790.068*0.219 (3)
C4E0.5237 (11)0.3686 (10)0.0357 (5)0.082 (11)*0.219 (3)
H4E0.43570.38400.00880.098*0.219 (3)
C5E0.5134 (10)0.3477 (10)0.1129 (5)0.05 (2)*0.219 (3)
H5E0.41960.34930.13970.058*0.219 (3)
C6E0.6418 (8)0.3241 (7)0.1516 (4)0.046 (8)*0.219 (3)
H6E0.63420.30830.20510.055*0.219 (3)
C11E0.9116 (5)0.2760 (4)0.1475 (2)0.027 (2)*0.219 (3)
H11F1.02720.34060.13770.032*0.219 (3)
C12E0.9060 (6)0.2405 (4)0.2326 (2)0.032 (2)*0.219 (3)
H12E0.80320.24160.25720.038*0.219 (3)
C13E1.0669 (7)0.3165 (5)0.2832 (3)0.030 (5)*0.219 (3)
C21E0.9327 (11)0.3345 (9)0.0807 (3)0.046 (7)*0.219 (3)
H21I0.93260.41760.10130.055*0.219 (3)
H21J0.83090.25870.10280.055*0.219 (3)
C22E1.0906 (11)0.3132 (10)0.1023 (3)0.042 (6)*0.219 (3)
H22M1.09400.30630.15890.064*0.219 (3)
H22N1.08920.23060.08170.064*0.219 (3)
H22O1.19050.38880.08020.064*0.219 (3)
O11E1.0434 (9)0.3064 (6)0.3571 (2)0.080 (7)*0.219 (3)
H1E1.13470.34960.38280.120*0.219 (3)
O12E1.2057 (7)0.3665 (5)0.2568 (3)0.021 (4)*0.219 (3)
O21E0.9338 (9)0.3439 (6)0.0027 (3)0.037 (5)*0.219 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.062 (3)0.037 (2)0.047 (2)0.0166 (17)0.0209 (17)0.0076 (19)
C2A0.055 (3)0.043 (3)0.046 (2)0.0163 (19)0.0128 (17)0.0005 (17)
C3A0.057 (3)0.057 (3)0.049 (2)0.022 (2)0.0053 (17)0.0001 (18)
C4A0.051 (3)0.065 (3)0.068 (3)0.026 (2)0.0099 (17)0.0010 (19)
C5A0.054 (4)0.061 (4)0.073 (4)0.026 (2)0.032 (3)0.004 (2)
C6A0.067 (3)0.051 (2)0.049 (2)0.0234 (19)0.0219 (18)0.006 (2)
C11A0.064 (2)0.0350 (18)0.0390 (19)0.0179 (16)0.0141 (15)0.0039 (14)
C12A0.073 (2)0.043 (2)0.0396 (19)0.0179 (18)0.0213 (16)0.0057 (15)
C13A0.079 (3)0.038 (2)0.035 (2)0.021 (2)0.0134 (19)0.0037 (19)
C21A0.055 (3)0.065 (3)0.027 (2)0.023 (2)0.0071 (14)0.0005 (17)
C22A0.052 (3)0.074 (3)0.0344 (19)0.025 (2)0.0119 (16)0.0048 (19)
O11A0.0656 (18)0.0661 (17)0.0375 (14)0.0193 (17)0.0139 (13)0.0116 (13)
O12A0.084 (2)0.056 (2)0.048 (2)0.0220 (14)0.0362 (14)0.0090 (11)
O21A0.052 (2)0.073 (2)0.0307 (13)0.0221 (14)0.0101 (10)0.0030 (12)
C1B0.045 (3)0.041 (2)0.0322 (18)0.0155 (17)0.0051 (13)0.0075 (16)
C2B0.035 (3)0.042 (3)0.037 (3)0.0146 (16)0.0055 (14)0.0038 (15)
C3B0.036 (2)0.066 (3)0.033 (2)0.0201 (18)0.0036 (13)0.0001 (15)
C4B0.035 (2)0.076 (3)0.041 (3)0.0251 (18)0.0009 (14)0.0052 (17)
C5B0.042 (5)0.067 (8)0.058 (7)0.027 (3)0.013 (2)0.0044 (18)
C6B0.053 (3)0.050 (2)0.034 (2)0.0181 (19)0.0106 (16)0.0026 (16)
C11B0.0470 (18)0.0352 (18)0.0308 (16)0.0150 (15)0.0065 (13)0.0021 (13)
C12B0.0509 (19)0.047 (2)0.0294 (17)0.0183 (16)0.0047 (13)0.0010 (13)
C13B0.061 (2)0.044 (2)0.031 (2)0.0213 (19)0.0043 (16)0.0052 (17)
C21B0.038 (2)0.050 (2)0.0244 (18)0.0148 (16)0.0016 (12)0.0011 (17)
C22B0.053 (3)0.068 (3)0.0356 (19)0.0277 (19)0.0081 (15)0.0062 (18)
O11B0.0596 (15)0.0717 (16)0.0205 (13)0.0356 (14)0.0095 (10)0.0109 (10)
O12B0.065 (2)0.067 (2)0.0358 (18)0.0230 (13)0.0127 (11)0.0117 (11)
O21B0.0390 (18)0.065 (2)0.0256 (12)0.0242 (12)0.0025 (9)0.0026 (12)
C1C0.0422 (13)0.0402 (14)0.0339 (13)0.0144 (11)0.0065 (10)0.0016 (10)
C2C0.0377 (13)0.0492 (15)0.0359 (13)0.0157 (12)0.0068 (10)0.0019 (11)
C3C0.0438 (15)0.084 (2)0.0449 (15)0.0272 (14)0.0041 (12)0.0077 (14)
C4C0.0408 (15)0.093 (2)0.0596 (18)0.0310 (15)0.0026 (13)0.0077 (15)
C5C0.0442 (15)0.074 (2)0.0641 (18)0.0273 (14)0.0196 (13)0.0104 (14)
C6C0.0549 (16)0.0540 (16)0.0412 (14)0.0224 (13)0.0181 (12)0.0058 (12)
C11C0.0434 (14)0.0404 (14)0.0349 (13)0.0150 (11)0.0075 (10)0.0002 (10)
C12C0.0526 (15)0.0554 (16)0.0304 (13)0.0200 (13)0.0096 (11)0.0026 (11)
C13C0.0586 (16)0.0447 (15)0.0285 (13)0.0172 (13)0.0053 (11)0.0018 (10)
C21C0.0424 (13)0.0601 (16)0.0258 (12)0.0208 (12)0.0052 (9)0.0087 (10)
C22C0.0438 (14)0.0627 (16)0.0326 (13)0.0208 (13)0.0068 (10)0.0040 (11)
O11C0.0586 (11)0.0858 (14)0.0307 (9)0.0270 (10)0.0060 (8)0.0133 (8)
O12C0.0601 (11)0.0692 (12)0.0342 (9)0.0269 (10)0.0106 (8)0.0026 (8)
O21C0.0373 (9)0.0726 (12)0.0267 (8)0.0223 (8)0.0026 (6)0.0032 (7)
Geometric parameters (Å, º) top
C1A—C6A1.388 (4)C12C—C13C1.468 (3)
C1A—C2A1.402 (6)C12C—H12C0.9500
C1A—C11A1.471 (5)C13C—O12C1.254 (2)
C2A—O21A1.366 (3)C13C—O11C1.293 (2)
C2A—C3A1.395 (5)C21C—O21C1.436 (2)
C3A—C4A1.372 (4)C21C—C22C1.501 (3)
C3A—H3A0.9500C21C—H21E0.9900
C4A—C5A1.395 (5)C21C—H21F0.9900
C4A—H4A0.9500C22C—H22G0.9800
C5A—C6A1.365 (5)C22C—H22H0.9800
C5A—H5A0.9500C22C—H22I0.9800
C6A—H6A0.9500O11C—H1C0.8400
C11A—C12A1.330 (4)C1D—C2D1.3865
C11A—H11A0.9500C1D—C6D1.3961
C12A—C13A1.461 (5)C1D—C11D1.4980
C12A—H12A0.9500C2D—O21D1.3716
C13A—O12A1.261 (4)C2D—C3D1.4117
C13A—O11A1.266 (4)C3D—C4D1.3884
C21A—O21A1.449 (4)C3D—H3D0.9500
C21A—C22A1.497 (4)C4D—C5D1.3674
C21A—H21A0.9900C4D—H4D0.9500
C21A—H21B0.9900C5D—C6D1.3890
C22A—H22A0.9800C5D—H5D0.9500
C22A—H22B0.9800C6D—H6D0.9500
C22A—H22C0.9800C11D—C12D1.5394
O11A—H1A0.8400C11D—C12E1.6166
C1B—C6B1.389 (5)C11D—H11D1.0000
C1B—C2B1.412 (5)C12D—C13D1.5337
C1B—C11B1.464 (4)C12D—C11E1.6083
C2B—O21B1.365 (3)C12D—H12D1.0000
C2B—C3B1.383 (4)C13D—O12D1.2148
C3B—C4B1.372 (4)C13D—O11D1.3233
C3B—H3B0.9500C21D—O21D1.4229
C4B—C5B1.386 (4)C21D—C22D1.5150
C4B—H4B0.9500C21D—H21G0.9900
C5B—C6B1.370 (5)C21D—H21H0.9900
C5B—H5B0.9500C22D—H22J0.9800
C6B—H6B0.9500C22D—H22K0.9800
C11B—C12B1.339 (3)C22D—H22L0.9800
C11B—H11B0.9500O11D—H1D0.8400
C12B—C13B1.459 (4)C1E—C2E1.3829
C12B—H12B0.9500C1E—C6E1.3919
C13B—O12B1.257 (3)C1E—C11E1.5117
C13B—O11B1.283 (3)C2E—O21E1.3878
C21B—O21B1.437 (4)C2E—C3E1.3985
C21B—C22B1.496 (3)C3E—C4E1.3933
C21B—H21C0.9900C3E—H3E0.9500
C21B—H21D0.9900C4E—C5E1.3664
C22B—H22D0.9800C4E—H4E0.9500
C22B—H22E0.9800C5E—C6E1.3866
C22B—H22F0.9800C5E—H5E0.9500
O11B—H1B0.8400C6E—H6E0.9500
C1C—C6C1.401 (3)C11E—C12E1.5393
C1C—C2C1.403 (3)C11E—H11F1.0000
C1C—C11C1.462 (3)C12E—C13E1.5245
C2C—O21C1.366 (2)C12E—H12E1.0000
C2C—C3C1.391 (3)C13E—O12E1.2245
C3C—C4C1.378 (3)C13E—O11E1.3047
C3C—H3C0.9500C21E—O21E1.4391
C4C—C5C1.375 (3)C21E—C22E1.5213
C4C—H4C0.9500C21E—H21I0.9900
C5C—C6C1.373 (3)C21E—H21J0.9900
C5C—H5C0.9500C22E—H22M0.9800
C6C—H6C0.9500C22E—H22N0.9800
C11C—C12C1.329 (3)C22E—H22O0.9800
C11C—H11C0.9500O11E—H1E0.8400
C6A—C1A—C2A117.8 (4)O21C—C21C—C22C106.88 (16)
C6A—C1A—C11A122.5 (4)O21C—C21C—H21E110.3
C2A—C1A—C11A119.7 (3)C22C—C21C—H21E110.3
O21A—C2A—C3A123.3 (5)O21C—C21C—H21F110.3
O21A—C2A—C1A116.3 (4)C22C—C21C—H21F110.3
C3A—C2A—C1A120.4 (3)H21E—C21C—H21F108.6
C4A—C3A—C2A120.1 (4)C21C—C22C—H22G109.5
C4A—C3A—H3A119.9C21C—C22C—H22H109.5
C2A—C3A—H3A119.9H22G—C22C—H22H109.5
C3A—C4A—C5A119.9 (3)C21C—C22C—H22I109.5
C3A—C4A—H4A120.0H22G—C22C—H22I109.5
C5A—C4A—H4A120.0H22H—C22C—H22I109.5
C6A—C5A—C4A119.6 (4)C13C—O11C—H1C109.5
C6A—C5A—H5A120.2C2C—O21C—C21C118.50 (15)
C4A—C5A—H5A120.2C2D—C1D—C6D117.6
C5A—C6A—C1A122.1 (5)C2D—C1D—C11D116.5
C5A—C6A—H6A118.9C6D—C1D—C11D125.3
C1A—C6A—H6A118.9O21D—C2D—C1D115.0
C12A—C11A—C1A127.0 (3)O21D—C2D—C3D124.0
C12A—C11A—H11A116.5C1D—C2D—C3D121.0
C1A—C11A—H11A116.5C4D—C3D—C2D118.8
C11A—C12A—C13A122.4 (3)C4D—C3D—H3D120.6
C11A—C12A—H12A118.8C2D—C3D—H3D120.6
C13A—C12A—H12A118.8C5D—C4D—C3D121.6
O12A—C13A—O11A125.0 (4)C5D—C4D—H4D119.2
O12A—C13A—C12A119.5 (3)C3D—C4D—H4D119.2
O11A—C13A—C12A115.5 (3)C4D—C5D—C6D118.6
O21A—C21A—C22A106.3 (4)C4D—C5D—H5D120.7
O21A—C21A—H21A110.5C6D—C5D—H5D120.7
C22A—C21A—H21A110.5C5D—C6D—C1D122.5
O21A—C21A—H21B110.5C5D—C6D—H6D118.7
C22A—C21A—H21B110.5C1D—C6D—H6D118.7
H21A—C21A—H21B108.7C1D—C11D—C12D119.2
C21A—C22A—H22A109.5C1D—C11D—C12E116.5
C21A—C22A—H22B109.5C12D—C11D—C12E89.6
H22A—C22A—H22B109.5C1D—C11D—H11D110.0
C21A—C22A—H22C109.5C12D—C11D—H11D110.0
H22A—C22A—H22C109.5C12E—C11D—H11D110.0
H22B—C22A—H22C109.5C13D—C12D—C11D114.6
C13A—O11A—H1A109.5C13D—C12D—C11E112.4
C2A—O21A—C21A118.9 (3)C11D—C12D—C11E90.4
C6B—C1B—C2B117.8 (3)C13D—C12D—H12D112.6
C6B—C1B—C11B121.9 (4)C11D—C12D—H12D112.6
C2B—C1B—C11B120.3 (3)C11E—C12D—H12D112.6
O21B—C2B—C3B123.6 (4)O12D—C13D—O11D122.4
O21B—C2B—C1B116.1 (3)O12D—C13D—C12D124.0
C3B—C2B—C1B120.4 (3)O11D—C13D—C12D113.0
C4B—C3B—C2B119.9 (3)O21D—C21D—C22D107.7
C4B—C3B—H3B120.0O21D—C21D—H21G110.2
C2B—C3B—H3B120.0C22D—C21D—H21G110.2
C3B—C4B—C5B120.7 (3)O21D—C21D—H21H110.2
C3B—C4B—H4B119.6C22D—C21D—H21H110.2
C5B—C4B—H4B119.6H21G—C21D—H21H108.5
C6B—C5B—C4B119.4 (5)C21D—C22D—H22J109.5
C6B—C5B—H5B120.3C21D—C22D—H22K109.5
C4B—C5B—H5B120.3H22J—C22D—H22K109.5
C5B—C6B—C1B121.7 (4)C21D—C22D—H22L109.5
C5B—C6B—H6B119.1H22J—C22D—H22L109.5
C1B—C6B—H6B119.1H22K—C22D—H22L109.5
C12B—C11B—C1B126.5 (3)C13D—O11D—H1D109.5
C12B—C11B—H11B116.7C2D—O21D—C21D118.0
C1B—C11B—H11B116.7C2E—C1E—C6E118.5
C11B—C12B—C13B121.9 (3)C2E—C1E—C11E115.6
C11B—C12B—H12B119.1C6E—C1E—C11E124.9
C13B—C12B—H12B119.1C1E—C2E—O21E115.2
O12B—C13B—O11B124.2 (3)C1E—C2E—C3E120.7
O12B—C13B—C12B121.4 (3)O21E—C2E—C3E124.1
O11B—C13B—C12B114.3 (3)C4E—C3E—C2E119.0
O21B—C21B—C22B107.0 (3)C4E—C3E—H3E120.5
O21B—C21B—H21C110.3C2E—C3E—H3E120.5
C22B—C21B—H21C110.3C5E—C4E—C3E121.3
O21B—C21B—H21D110.3C5E—C4E—H4E119.4
C22B—C21B—H21D110.3C3E—C4E—H4E119.4
H21C—C21B—H21D108.6C4E—C5E—C6E119.0
C21B—C22B—H22D109.5C4E—C5E—H5E120.5
C21B—C22B—H22E109.5C6E—C5E—H5E120.5
H22D—C22B—H22E109.5C5E—C6E—C1E121.6
C21B—C22B—H22F109.5C5E—C6E—H6E119.2
H22D—C22B—H22F109.5C1E—C6E—H6E119.2
H22E—C22B—H22F109.5C1E—C11E—C12E119.6
C13B—O11B—H1B109.5C1E—C11E—C12D116.7
C2B—O21B—C21B118.1 (3)C12E—C11E—C12D89.9
C6C—C1C—C2C117.9 (2)C1E—C11E—H11F109.7
C6C—C1C—C11C122.2 (2)C12E—C11E—H11F109.7
C2C—C1C—C11C119.83 (19)C12D—C11E—H11F109.7
O21C—C2C—C3C123.5 (2)C13E—C12E—C11E115.4
O21C—C2C—C1C116.24 (19)C13E—C12E—C11D112.1
C3C—C2C—C1C120.3 (2)C11E—C12E—C11D90.1
C4C—C3C—C2C119.7 (2)C13E—C12E—H12E112.5
C4C—C3C—H3C120.2C11E—C12E—H12E112.5
C2C—C3C—H3C120.2C11D—C12E—H12E112.5
C5C—C4C—C3C121.2 (2)O12E—C13E—O11E123.8
C5C—C4C—H4C119.4O12E—C13E—C12E123.0
C3C—C4C—H4C119.4O11E—C13E—C12E112.5
C6C—C5C—C4C119.3 (2)O21E—C21E—C22E107.3
C6C—C5C—H5C120.3O21E—C21E—H21I110.3
C4C—C5C—H5C120.3C22E—C21E—H21I110.3
C5C—C6C—C1C121.6 (2)O21E—C21E—H21J110.3
C5C—C6C—H6C119.2C22E—C21E—H21J110.3
C1C—C6C—H6C119.2H21I—C21E—H21J108.5
C12C—C11C—C1C126.7 (2)C21E—C22E—H22M109.5
C12C—C11C—H11C116.6C21E—C22E—H22N109.5
C1C—C11C—H11C116.6H22M—C22E—H22N109.5
C11C—C12C—C13C122.2 (2)C21E—C22E—H22O109.5
C11C—C12C—H12C118.9H22M—C22E—H22O109.5
C13C—C12C—H12C118.9H22N—C22E—H22O109.5
O12C—C13C—O11C123.3 (2)C13E—O11E—H1E109.5
O12C—C13C—C12C121.7 (2)C2E—O21E—C21E117.6
O11C—C13C—C12C115.0 (2)
C6A—C1A—C2A—O21A179.9 (4)C6D—C1D—C2D—C3D1.6
C11A—C1A—C2A—O21A0.0 (6)C11D—C1D—C2D—C3D172.7
C6A—C1A—C2A—C3A0.0 (6)O21D—C2D—C3D—C4D179.8
C11A—C1A—C2A—C3A179.8 (4)C1D—C2D—C3D—C4D1.7
O21A—C2A—C3A—C4A179.1 (4)C2D—C3D—C4D—C5D1.5
C1A—C2A—C3A—C4A1.0 (7)C3D—C4D—C5D—C6D1.1
C2A—C3A—C4A—C5A1.7 (8)C4D—C5D—C6D—C1D1.0
C3A—C4A—C5A—C6A1.4 (8)C2D—C1D—C6D—C5D1.3
C4A—C5A—C6A—C1A0.4 (8)C11D—C1D—C6D—C5D171.5
C2A—C1A—C6A—C5A0.3 (7)C2D—C1D—C11D—C12D176.6
C11A—C1A—C6A—C5A179.8 (4)C6D—C1D—C11D—C12D13.1
C6A—C1A—C11A—C12A1.7 (6)C2D—C1D—C11D—C12E77.8
C2A—C1A—C11A—C12A178.5 (4)C6D—C1D—C11D—C12E92.6
C1A—C11A—C12A—C13A179.4 (4)C1D—C11D—C12D—C13D125.2
C11A—C12A—C13A—O12A1.2 (6)C12E—C11D—C12D—C13D114.3
C11A—C12A—C13A—O11A179.0 (3)C1D—C11D—C12D—C11E119.8
C3A—C2A—O21A—C21A0.6 (6)C12E—C11D—C12D—C11E0.7
C1A—C2A—O21A—C21A179.2 (3)C11D—C12D—C13D—O12D31.8
C22A—C21A—O21A—C2A175.1 (3)C11E—C12D—C13D—O12D69.5
C6B—C1B—C2B—O21B179.5 (4)C11D—C12D—C13D—O11D157.0
C11B—C1B—C2B—O21B1.6 (6)C11E—C12D—C13D—O11D101.6
C6B—C1B—C2B—C3B0.8 (7)C1D—C2D—O21D—C21D169.1
C11B—C1B—C2B—C3B178.8 (4)C3D—C2D—O21D—C21D12.3
O21B—C2B—C3B—C4B179.7 (5)C22D—C21D—O21D—C2D174.3
C1B—C2B—C3B—C4B0.6 (8)C6E—C1E—C2E—O21E179.2
C2B—C3B—C4B—C5B0.7 (9)C11E—C1E—C2E—O21E11.3
C3B—C4B—C5B—C6B1.0 (8)C6E—C1E—C2E—C3E0.3
C4B—C5B—C6B—C1B1.3 (7)C11E—C1E—C2E—C3E169.8
C2B—C1B—C6B—C5B1.1 (7)C1E—C2E—C3E—C4E0.1
C11B—C1B—C6B—C5B179.1 (4)O21E—C2E—C3E—C4E178.7
C6B—C1B—C11B—C12B8.6 (6)C2E—C3E—C4E—C5E0.0
C2B—C1B—C11B—C12B173.5 (3)C3E—C4E—C5E—C6E0.5
C1B—C11B—C12B—C13B179.1 (4)C4E—C5E—C6E—C1E0.9
C11B—C12B—C13B—O12B5.7 (6)C2E—C1E—C6E—C5E0.8
C11B—C12B—C13B—O11B173.1 (3)C11E—C1E—C6E—C5E169.2
C3B—C2B—O21B—C21B1.6 (6)C2E—C1E—C11E—C12E176.1
C1B—C2B—O21B—C21B178.0 (3)C6E—C1E—C11E—C12E7.4
C22B—C21B—O21B—C2B176.4 (3)C2E—C1E—C11E—C12D69.7
C6C—C1C—C2C—O21C179.7 (2)C6E—C1E—C11E—C12D99.1
C11C—C1C—C2C—O21C1.6 (3)C13D—C12D—C11E—C1E7.3
C6C—C1C—C2C—C3C0.4 (3)C11D—C12D—C11E—C1E124.2
C11C—C1C—C2C—C3C178.3 (2)C13D—C12D—C11E—C12E116.2
O21C—C2C—C3C—C4C179.7 (2)C11D—C12D—C11E—C12E0.7
C1C—C2C—C3C—C4C0.1 (4)C1E—C11E—C12E—C13E123.6
C2C—C3C—C4C—C5C0.7 (4)C12D—C11E—C12E—C13E115.4
C3C—C4C—C5C—C6C0.7 (4)C1E—C11E—C12E—C11D121.7
C4C—C5C—C6C—C1C0.1 (4)C12D—C11E—C12E—C11D0.7
C2C—C1C—C6C—C5C0.4 (3)C1D—C11D—C12E—C13E4.5
C11C—C1C—C6C—C5C178.3 (2)C12D—C11D—C12E—C13E118.3
C6C—C1C—C11C—C12C2.3 (4)C1D—C11D—C12E—C11E122.1
C2C—C1C—C11C—C12C176.4 (2)C12D—C11D—C12E—C11E0.7
C1C—C11C—C12C—C13C178.4 (2)C11E—C12E—C13E—O12E23.8
C11C—C12C—C13C—O12C4.8 (4)C11D—C12E—C13E—O12E77.5
C11C—C12C—C13C—O11C175.5 (2)C11E—C12E—C13E—O11E165.0
C3C—C2C—O21C—C21C1.5 (3)C11D—C12E—C13E—O11E93.7
C1C—C2C—O21C—C21C178.32 (19)C1E—C2E—O21E—C21E165.9
C22C—C21C—O21C—C2C175.72 (19)C3E—C2E—O21E—C21E15.2
C6D—C1D—C2D—O21D179.8C22E—C21E—O21E—C2E171.1
C11D—C1D—C2D—O21D8.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11A—H1A···O12Ai0.841.702.522 (5)166
O11B—H1B···O12Cii0.841.762.590 (3)170
O11C—H1C···O12Bii0.841.782.607 (4)168
O11E—H1E···O12Cii0.842.092.823 (6)146
O11C—H1C···O12Eii0.841.922.75 (2)169
O11D—H1D···O12Di0.842.333.094 (11)152
O11D—H1D···O12Ai0.842.182.929 (6)148
O11A—H1A···O12Di0.841.842.671 (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 = 576.62F(000) = 612
Triclinic, P1Dx = 1.293 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4919 (13) ÅCell parameters from 864 reflections
b = 10.9148 (17) Åθ = 2.6–27.2°
c = 17.372 (3) ŵ = 0.09 mm1
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 tubeRint = 0.030
Graphite monochromatorθmax = 25.5°, θmin = 1.2°
phi and ω scansh = 1010
8447 measured reflectionsk = 137
5471 independent reflectionsl = 2119
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H 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 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
0.680(C22H24O6)·1.640(C11H12O3)γ = 111.956 (3)°
Mr = 576.62V = 1480.8 (4) Å3
Triclinic, P1Z = 2
a = 8.4919 (13) ÅMo Kα radiation
b = 10.9148 (17) ŵ = 0.09 mm1
c = 17.372 (3) ÅT = 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 reflectionsRint = 0.030
5471 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.172H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.19 e Å3
5471 reflectionsΔρmin = 0.35 e Å3
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
xyzUiso*/UeqOcc. (<1)
C1A1.0102 (5)0.0233 (4)0.2193 (2)0.0459 (11)*0.320 (4)
C2A1.0033 (5)0.0191 (4)0.2995 (2)0.0459 (11)*0.320 (4)
C3A1.1444 (5)0.0276 (4)0.3445 (2)0.0459 (11)*0.320 (4)
H3A1.14000.02700.39910.055*0.320 (4)
C4A1.2915 (5)0.0368 (4)0.3103 (2)0.0459 (11)*0.320 (4)
H4A1.38820.04170.34140.055*0.320 (4)
C5A1.3003 (5)0.0390 (4)0.2316 (2)0.0459 (11)*0.320 (4)
H5A1.40230.04500.20830.055*0.320 (4)
C6A1.1617 (5)0.0326 (4)0.1870 (2)0.0459 (11)*0.320 (4)
H6A1.16870.03450.13260.055*0.320 (4)
C11A0.8578 (5)0.0102 (4)0.1700 (2)0.0260 (14)0.320 (4)
H11A0.75970.00460.19650.031*0.320 (4)
C12A0.8410 (5)0.0053 (4)0.0927 (2)0.0260 (14)0.32
H12A0.93610.01040.06390.031*0.320 (4)
C13A0.6829 (5)0.0076 (4)0.0510 (2)0.0459 (11)*0.320 (4)
C21A0.8391 (5)0.0105 (4)0.4111 (2)0.0459 (11)*0.320 (4)
H21A0.92910.09100.43920.055*0.320 (4)
H21B0.85230.06910.42820.055*0.320 (4)
C22A0.6671 (5)0.0101 (4)0.4272 (2)0.0459 (11)*0.320 (4)
H22A0.65360.01070.48300.069*0.320 (4)
H22B0.57920.07000.39910.069*0.320 (4)
H22C0.65570.08930.41010.069*0.320 (4)
O11A0.6798 (5)0.0107 (4)0.0225 (2)0.0459 (11)*0.320 (4)
H1A0.58280.01830.04000.069*0.320 (4)
O12A0.5579 (5)0.0151 (4)0.0905 (2)0.0459 (11)*0.320 (4)
O21A0.8524 (5)0.0096 (4)0.3288 (2)0.0459 (11)*0.320 (4)
C1B0.7683 (6)0.3328 (4)0.1230 (3)0.0459 (11)*0.320 (4)
C2B0.7682 (6)0.3202 (4)0.0417 (3)0.0459 (11)*0.320 (4)
C3B0.6297 (6)0.3173 (4)0.0036 (3)0.0459 (11)*0.320 (4)
H3B0.63040.30890.05850.055*0.320 (4)
C4B0.4908 (6)0.3269 (4)0.0315 (3)0.0459 (11)*0.320 (4)
H4B0.39590.32520.00030.055*0.320 (4)
C5B0.4877 (6)0.3389 (4)0.1111 (3)0.0459 (11)*0.320 (4)
H5B0.39120.34500.13490.055*0.320 (4)
C6B0.6262 (6)0.3421 (4)0.1559 (3)0.0459 (11)*0.320 (4)
H6B0.62410.35080.21080.055*0.320 (4)
C11B0.9176 (6)0.3425 (4)0.1719 (3)0.029 (2)0.320 (4)
H11B1.01650.34840.14590.035*0.320 (4)
C12B0.9303 (6)0.3440 (4)0.2491 (3)0.033 (2)0.320 (4)
H12B0.83430.33900.27720.040*0.320 (4)
C13B1.0858 (6)0.3529 (4)0.2917 (3)0.0459 (11)*0.320 (4)
C21B0.9137 (6)0.2925 (4)0.0712 (3)0.0459 (11)*0.320 (4)
H21C0.90690.37000.09390.055*0.320 (4)
H21D0.81570.21180.09360.055*0.320 (4)
C22B1.0774 (6)0.2770 (4)0.0882 (3)0.0459 (11)*0.320 (4)
H22D1.08360.26340.14450.069*0.320 (4)
H22E1.08250.20000.06540.069*0.320 (4)
H22F1.17330.35750.06580.069*0.320 (4)
O11B1.0738 (6)0.3400 (4)0.3644 (3)0.0459 (11)*0.320 (4)
H1B1.16810.34640.38460.069*0.320 (4)
O12B1.2199 (6)0.3713 (4)0.2570 (3)0.0459 (11)*0.320 (4)
O21B0.9109 (6)0.3120 (4)0.0116 (3)0.0459 (11)*0.320 (4)
C1C0.2290 (3)0.6603 (3)0.42850 (15)0.0361 (7)
C2C0.2347 (3)0.6616 (3)0.34800 (15)0.0409 (7)
C3C0.0909 (4)0.6494 (4)0.30222 (18)0.0622 (10)
H3C0.09430.64730.24750.075*
C4C0.0566 (4)0.6403 (4)0.33658 (19)0.0687 (11)
H4C0.15440.63190.30510.082*
C5C0.0644 (4)0.6431 (3)0.41581 (19)0.0584 (9)
H5C0.16600.63840.43910.070*
C6C0.0777 (4)0.6531 (3)0.46085 (16)0.0448 (8)
H6C0.07250.65500.51550.054*
C11C0.3762 (3)0.6628 (3)0.47506 (14)0.0355 (7)
H11C0.47600.67240.44900.043*
C12C0.3836 (4)0.6530 (3)0.55101 (15)0.0419 (8)
H12C0.28830.64870.57940.050*
C13C0.5352 (4)0.6487 (3)0.59173 (15)0.0405 (7)
C21C0.4002 (3)0.6823 (3)0.23676 (14)0.0405 (7)
H21E0.37940.76080.22270.049*
H21F0.31550.60140.20630.049*
C22C0.5766 (3)0.6944 (3)0.21995 (15)0.0459 (8)
H22G0.65930.77070.25340.069*
H22H0.59370.70750.16540.069*
H22I0.59250.61290.23000.069*
O11C0.5129 (2)0.6252 (2)0.66392 (10)0.0553 (6)
H1C0.60280.62400.68470.083*
O12C0.6690 (2)0.6644 (2)0.56122 (10)0.0492 (6)
O21C0.3863 (2)0.6741 (2)0.31848 (9)0.0429 (5)
C1D1.0114 (5)0.0400 (4)0.2308 (2)0.0363 (11)0.680 (4)
C2D0.9970 (5)0.0023 (4)0.3053 (2)0.0322 (10)0.680 (4)
C3D1.1266 (5)0.0248 (5)0.3425 (2)0.0414 (12)0.680 (4)
H3D1.11580.05050.39330.050*0.680 (4)
C4D1.2710 (6)0.0134 (5)0.3042 (3)0.0462 (13)0.680 (4)
H4D1.36010.03070.32930.055*0.680 (4)
C5D1.2879 (6)0.0223 (5)0.2304 (3)0.0457 (12)0.680 (4)
H5D1.38640.02770.20420.055*0.680 (4)
C6D1.1590 (6)0.0503 (5)0.1947 (3)0.0473 (12)0.680 (4)
H6D1.17200.07730.14430.057*0.680 (4)
C11D0.8789 (5)0.0861 (5)0.2007 (2)0.0396 (12)0.680 (4)
H11D0.76310.02220.20990.048*0.680 (4)
C12D0.8803 (5)0.1194 (4)0.1167 (2)0.0400 (12)0.680 (4)
H12D0.98170.11500.09060.048*0.680 (4)
C13D0.7140 (6)0.0450 (5)0.0665 (2)0.0385 (11)0.680 (4)
C21D0.8376 (5)0.0210 (5)0.4179 (2)0.0420 (12)0.680 (4)
H21G0.93370.05110.44890.050*0.680 (4)
H21H0.84230.10750.42740.050*0.680 (4)
C22D0.6712 (5)0.0145 (5)0.4406 (2)0.0424 (12)0.680 (4)
H22J0.67180.07410.43510.064*0.680 (4)
H22K0.65590.03150.49470.064*0.680 (4)
H22L0.57760.08180.40680.064*0.680 (4)
O11D0.7335 (4)0.0386 (3)0.00881 (16)0.0438 (8)0.680 (4)
H1D0.63920.00650.03340.066*0.680 (4)
O12D0.5755 (4)0.0105 (3)0.09238 (18)0.0482 (9)0.680 (4)
O21D0.8491 (3)0.0064 (3)0.33750 (16)0.0355 (8)0.680 (4)
C1E0.7733 (5)0.3205 (4)0.1170 (2)0.0340 (10)0.680 (4)
C2E0.7806 (5)0.3420 (4)0.0397 (2)0.0292 (10)0.680 (4)
C3E0.6503 (6)0.3651 (5)0.0009 (3)0.0482 (13)0.680 (4)
H3E0.65500.37790.05240.058*0.680 (4)
C4E0.5137 (6)0.3690 (6)0.0414 (3)0.0561 (15)0.680 (4)
H4E0.42470.38570.01560.067*0.680 (4)
C5E0.5049 (6)0.3493 (5)0.1182 (3)0.0512 (13)0.680 (4)
H5E0.41130.35310.14560.061*0.680 (4)
C6E0.6340 (6)0.3237 (5)0.1555 (3)0.0416 (12)0.680 (4)
H6E0.62690.30820.20830.050*0.680 (4)
C11E0.9036 (5)0.2719 (5)0.1487 (2)0.0355 (12)0.680 (4)
H11E1.02050.33450.13990.043*0.680 (4)
C12E0.8994 (5)0.2389 (5)0.2329 (2)0.0422 (12)0.680 (4)
H12E0.79660.24240.25810.051*0.680 (4)
C13E1.0619 (5)0.3112 (4)0.2842 (2)0.0298 (10)0.680 (4)
C21E0.9221 (5)0.3291 (5)0.0771 (2)0.0359 (11)0.680 (4)
H21I0.92100.41190.09510.043*0.680 (4)
H21J0.81920.25370.10080.043*0.680 (4)
C22E1.0799 (6)0.3072 (5)0.1001 (2)0.0473 (13)0.680 (4)
H22M1.18090.38400.07790.071*0.680 (4)
H22N1.08010.29680.15680.071*0.680 (4)
H22O1.08140.22660.08050.071*0.680 (4)
O11E1.0399 (4)0.3009 (3)0.35768 (15)0.0355 (8)0.680 (4)
H1E1.13510.32770.38290.053*0.680 (4)
O12E1.2005 (4)0.3579 (3)0.25795 (17)0.0370 (8)0.680 (4)
O21E0.9243 (4)0.3392 (3)0.00591 (16)0.0346 (8)0.680 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C11A0.038 (3)0.010 (3)0.025 (3)0.006 (3)0.002 (3)0.009 (3)
C12A0.038 (3)0.010 (3)0.025 (3)0.006 (3)0.002 (3)0.009 (3)
C11B0.044 (6)0.012 (5)0.026 (5)0.006 (5)0.009 (4)0.007 (4)
C12B0.050 (6)0.028 (6)0.021 (5)0.017 (5)0.001 (4)0.010 (4)
C1C0.0408 (17)0.0375 (18)0.0303 (16)0.0147 (14)0.0073 (13)0.0050 (13)
C2C0.0349 (17)0.058 (2)0.0342 (16)0.0210 (16)0.0084 (13)0.0103 (14)
C3C0.0477 (19)0.113 (3)0.0391 (18)0.043 (2)0.0073 (15)0.0209 (19)
C4C0.043 (2)0.123 (3)0.057 (2)0.047 (2)0.0077 (16)0.024 (2)
C5C0.0438 (19)0.084 (3)0.059 (2)0.0335 (19)0.0204 (16)0.0205 (19)
C6C0.0501 (19)0.054 (2)0.0377 (17)0.0263 (17)0.0164 (14)0.0106 (15)
C11C0.0373 (16)0.0382 (18)0.0294 (16)0.0137 (14)0.0028 (12)0.0000 (13)
C12C0.0465 (18)0.053 (2)0.0277 (16)0.0199 (16)0.0092 (13)0.0053 (14)
C13C0.0518 (19)0.0429 (19)0.0236 (16)0.0148 (16)0.0025 (14)0.0025 (13)
C21C0.0415 (17)0.058 (2)0.0251 (15)0.0216 (16)0.0045 (12)0.0073 (14)
C22C0.0397 (17)0.062 (2)0.0341 (16)0.0178 (16)0.0044 (13)0.0009 (15)
O11C0.0488 (13)0.0884 (18)0.0293 (12)0.0237 (12)0.0044 (9)0.0183 (11)
O12C0.0480 (13)0.0676 (15)0.0323 (11)0.0224 (11)0.0084 (10)0.0047 (10)
O21C0.0357 (11)0.0703 (15)0.0263 (10)0.0232 (11)0.0042 (8)0.0088 (10)
C1D0.033 (2)0.037 (3)0.044 (3)0.016 (2)0.0080 (19)0.016 (2)
C2D0.035 (2)0.029 (2)0.034 (2)0.013 (2)0.0046 (18)0.0046 (18)
C3D0.045 (3)0.051 (3)0.034 (2)0.025 (2)0.000 (2)0.007 (2)
C4D0.041 (3)0.052 (3)0.052 (3)0.027 (3)0.004 (2)0.000 (2)
C5D0.036 (3)0.052 (3)0.053 (3)0.023 (2)0.008 (2)0.001 (2)
C6D0.048 (3)0.060 (3)0.045 (3)0.030 (3)0.014 (2)0.014 (2)
C11D0.040 (2)0.054 (3)0.031 (2)0.022 (2)0.0098 (19)0.014 (2)
C12D0.043 (3)0.055 (3)0.028 (2)0.025 (2)0.0051 (18)0.004 (2)
C13D0.057 (3)0.043 (3)0.027 (2)0.028 (3)0.017 (2)0.013 (2)
C21D0.048 (3)0.055 (3)0.028 (2)0.024 (2)0.0018 (19)0.008 (2)
C22D0.049 (3)0.061 (3)0.027 (2)0.029 (2)0.0079 (19)0.013 (2)
O11D0.0371 (18)0.055 (2)0.0294 (17)0.0053 (17)0.0042 (13)0.0069 (15)
O12D0.057 (2)0.045 (2)0.0393 (18)0.0137 (17)0.0191 (15)0.0111 (15)
O21D0.0296 (15)0.053 (2)0.0274 (16)0.0171 (14)0.0059 (12)0.0134 (13)
C1E0.031 (2)0.038 (3)0.034 (2)0.012 (2)0.0024 (18)0.0142 (19)
C2E0.029 (2)0.032 (2)0.026 (2)0.0115 (19)0.0004 (17)0.0007 (18)
C3E0.046 (3)0.073 (4)0.032 (2)0.029 (3)0.009 (2)0.008 (2)
C4E0.042 (3)0.082 (4)0.055 (3)0.036 (3)0.005 (2)0.011 (3)
C5E0.043 (3)0.070 (4)0.054 (3)0.036 (3)0.010 (2)0.011 (3)
C6E0.045 (3)0.047 (3)0.034 (2)0.018 (2)0.007 (2)0.007 (2)
C11E0.033 (2)0.044 (3)0.028 (2)0.012 (2)0.0005 (19)0.009 (2)
C12E0.042 (3)0.065 (4)0.028 (2)0.029 (3)0.0035 (19)0.007 (2)
C13E0.043 (3)0.029 (3)0.018 (2)0.015 (2)0.0034 (18)0.0015 (17)
C21E0.039 (2)0.050 (3)0.022 (2)0.019 (2)0.0003 (17)0.0085 (19)
C22E0.060 (3)0.065 (3)0.033 (2)0.039 (3)0.012 (2)0.016 (2)
O11E0.0452 (19)0.045 (2)0.0141 (14)0.0152 (16)0.0002 (12)0.0009 (13)
O12E0.0425 (18)0.0409 (19)0.0223 (15)0.0089 (15)0.0056 (13)0.0069 (13)
O21E0.0362 (16)0.048 (2)0.0227 (15)0.0193 (15)0.0023 (12)0.0069 (13)
Geometric parameters (Å, º) top
C1A—C6A1.3930C12C—C13C1.468 (4)
C1A—C2A1.4008C12C—H12C0.9500
C1A—C11A1.4821C13C—O12C1.230 (3)
C2A—O21A1.3649C13C—O11C1.312 (3)
C2A—C3A1.3788C21C—O21C1.437 (3)
C3A—C4A1.3737C21C—C22C1.495 (3)
C3A—H3A0.9500C21C—H21E0.9900
C4A—C5A1.3750C21C—H21F0.9900
C4A—H4A0.9500C22C—H22G0.9800
C5A—C6A1.3631C22C—H22H0.9800
C5A—H5A0.9500C22C—H22I0.9800
C6A—H6A0.9500O11C—H1C0.8400
C11A—C12A1.3389C1D—C6D1.391 (5)
C11A—H11A0.9500C1D—C2D1.395 (5)
C12A—C13A1.4585C1D—C11D1.495 (5)
C12A—H12A0.9500C2D—O21D1.365 (4)
C13A—O12A1.2635C2D—C3D1.399 (5)
C13A—O11A1.2715C3D—C4D1.385 (5)
C21A—O21A1.4363C3D—H3D0.9500
C21A—C22A1.4941C4D—C5D1.375 (6)
C21A—H21A0.9900C4D—H4D0.9500
C21A—H21B0.9900C5D—C6D1.387 (6)
C22A—H22A0.9800C5D—H5D0.9500
C22A—H22B0.9800C6D—H6D0.9500
C22A—H22C0.9800C11D—C12D1.539 (5)
O11A—H1A0.8400C11D—C12E1.645 (7)
C1B—C6B1.3842C11D—H11D1.0000
C1B—C2B1.4043C12D—C13D1.527 (6)
C1B—C11B1.4677C12D—C11E1.635 (6)
C2B—O21B1.3643C12D—H12D1.0000
C2B—C3B1.3827C13D—O12D1.210 (4)
C3B—C4B1.3764C13D—O11D1.322 (4)
C3B—H3B0.9500C21D—O21D1.424 (4)
C4B—C5B1.3784C21D—C22D1.504 (5)
C4B—H4B0.9500C21D—H21G0.9900
C5B—C6B1.3773C21D—H21H0.9900
C5B—H5B0.9500C22D—H22J0.9800
C6B—H6B0.9500C22D—H22K0.9800
C11B—C12B1.3405C22D—H22L0.9800
C11B—H11B0.9500O11D—H1D0.8400
C12B—C13B1.4590C1E—C6E1.386 (5)
C12B—H12B0.9500C1E—C2E1.387 (5)
C13B—O12B1.2632C1E—C11E1.507 (6)
C13B—O11B1.2894C2E—O21E1.379 (4)
C21B—O21B1.4331C2E—C3E1.393 (5)
C21B—C22B1.4962C3E—C4E1.388 (5)
C21B—H21C0.9900C3E—H3E0.9500
C21B—H21D0.9900C4E—C5E1.375 (6)
C22B—H22D0.9800C4E—H4E0.9500
C22B—H22E0.9800C5E—C6E1.385 (6)
C22B—H22F0.9800C5E—H5E0.9500
O11B—H1B0.8400C6E—H6E0.9500
C1C—C6C1.397 (3)C11E—C12E1.540 (5)
C1C—C2C1.402 (3)C11E—H11E1.0000
C1C—C11C1.457 (4)C12E—C13E1.511 (5)
C2C—O21C1.365 (3)C12E—H12E1.0000
C2C—C3C1.392 (4)C13E—O12E1.219 (4)
C3C—C4C1.378 (4)C13E—O11E1.306 (4)
C3C—H3C0.9500C21E—O21E1.434 (4)
C4C—C5C1.378 (4)C21E—C22E1.504 (5)
C4C—H4C0.9500C21E—H21I0.9900
C5C—C6C1.381 (4)C21E—H21J0.9900
C5C—H5C0.9500C22E—H22M0.9800
C6C—H6C0.9500C22E—H22N0.9800
C11C—C12C1.336 (3)C22E—H22O0.9800
C11C—H11C0.9500O11E—H1E0.8400
C6A—C1A—C2A117.9C11C—C12C—C13C121.8 (3)
C6A—C1A—C11A121.2C11C—C12C—H12C119.1
C2A—C1A—C11A120.9C13C—C12C—H12C119.1
O21A—C2A—C3A123.6O12C—C13C—O11C123.4 (3)
O21A—C2A—C1A116.0O12C—C13C—C12C123.6 (2)
C3A—C2A—C1A120.4O11C—C13C—C12C113.1 (3)
C4A—C3A—C2A119.9O21C—C21C—C22C107.2 (2)
C4A—C3A—H3A120.1O21C—C21C—H21E110.3
C2A—C3A—H3A120.1C22C—C21C—H21E110.3
C3A—C4A—C5A120.7O21C—C21C—H21F110.3
C3A—C4A—H4A119.7C22C—C21C—H21F110.3
C5A—C4A—H4A119.7H21E—C21C—H21F108.5
C6A—C5A—C4A119.6C21C—C22C—H22G109.5
C6A—C5A—H5A120.2C21C—C22C—H22H109.5
C4A—C5A—H5A120.2H22G—C22C—H22H109.5
C5A—C6A—C1A121.6C21C—C22C—H22I109.5
C5A—C6A—H6A119.2H22G—C22C—H22I109.5
C1A—C6A—H6A119.2H22H—C22C—H22I109.5
C12A—C11A—C1A128.2C13C—O11C—H1C109.5
C12A—C11A—H11A115.9C2C—O21C—C21C118.20 (19)
C1A—C11A—H11A115.9C6D—C1D—C2D117.9 (4)
C11A—C12A—C13A122.7C6D—C1D—C11D124.5 (4)
C11A—C12A—H12A118.7C2D—C1D—C11D117.0 (3)
C13A—C12A—H12A118.7O21D—C2D—C1D115.1 (3)
O12A—C13A—O11A124.5O21D—C2D—C3D123.8 (3)
O12A—C13A—C12A117.5C1D—C2D—C3D121.1 (4)
O11A—C13A—C12A118.0C4D—C3D—C2D118.9 (4)
O21A—C21A—C22A107.2C4D—C3D—H3D120.5
O21A—C21A—H21A110.3C2D—C3D—H3D120.5
C22A—C21A—H21A110.3C5D—C4D—C3D121.3 (4)
O21A—C21A—H21B110.3C5D—C4D—H4D119.4
C22A—C21A—H21B110.3C3D—C4D—H4D119.4
H21A—C21A—H21B108.5C4D—C5D—C6D119.1 (4)
C21A—C22A—H22A109.5C4D—C5D—H5D120.5
C21A—C22A—H22B109.5C6D—C5D—H5D120.5
H22A—C22A—H22B109.5C5D—C6D—C1D121.8 (4)
C21A—C22A—H22C109.5C5D—C6D—H6D119.1
H22A—C22A—H22C109.5C1D—C6D—H6D119.1
H22B—C22A—H22C109.5C1D—C11D—C12D119.4 (3)
C13A—O11A—H1A109.5C1D—C11D—C12E116.7 (4)
C2A—O21A—C21A118.8C12D—C11D—C12E90.0 (3)
C6B—C1B—C2B118.0C1D—C11D—H11D109.8
C6B—C1B—C11B120.8C12D—C11D—H11D109.8
C2B—C1B—C11B121.2C12E—C11D—H11D109.8
O21B—C2B—C3B123.3C13D—C12D—C11D115.2 (3)
O21B—C2B—C1B116.1C13D—C12D—C11E112.3 (3)
C3B—C2B—C1B120.6C11D—C12D—C11E90.1 (3)
C4B—C3B—C2B119.6C13D—C12D—H12D112.5
C4B—C3B—H3B120.2C11D—C12D—H12D112.5
C2B—C3B—H3B120.2C11E—C12D—H12D112.5
C3B—C4B—C5B120.9O12D—C13D—O11D122.6 (4)
C3B—C4B—H4B119.6O12D—C13D—C12D123.2 (4)
C5B—C4B—H4B119.6O11D—C13D—C12D113.6 (3)
C6B—C5B—C4B119.2O21D—C21D—C22D107.8 (3)
C6B—C5B—H5B120.4O21D—C21D—H21G110.1
C4B—C5B—H5B120.4C22D—C21D—H21G110.1
C5B—C6B—C1B121.7O21D—C21D—H21H110.1
C5B—C6B—H6B119.1C22D—C21D—H21H110.1
C1B—C6B—H6B119.1H21G—C21D—H21H108.5
C12B—C11B—C1B127.4C13D—O11D—H1D109.5
C12B—C11B—H11B116.3C2D—O21D—C21D118.2 (3)
C1B—C11B—H11B116.3C6E—C1E—C2E118.6 (4)
C11B—C12B—C13B122.5C6E—C1E—C11E124.3 (4)
C11B—C12B—H12B118.7C2E—C1E—C11E116.2 (4)
C13B—C12B—H12B118.7O21E—C2E—C1E115.1 (3)
O12B—C13B—O11B124.4O21E—C2E—C3E123.9 (3)
O12B—C13B—C12B120.1C1E—C2E—C3E121.0 (4)
O11B—C13B—C12B115.4C4E—C3E—C2E118.8 (4)
O21B—C21B—C22B107.2C4E—C3E—H3E120.6
O21B—C21B—H21C110.3C2E—C3E—H3E120.6
C22B—C21B—H21C110.3C5E—C4E—C3E121.0 (4)
O21B—C21B—H21D110.3C5E—C4E—H4E119.5
C22B—C21B—H21D110.3C3E—C4E—H4E119.5
H21C—C21B—H21D108.5C4E—C5E—C6E119.3 (4)
C21B—C22B—H22D109.5C4E—C5E—H5E120.3
C21B—C22B—H22E109.5C6E—C5E—H5E120.3
H22D—C22B—H22E109.5C5E—C6E—C1E121.2 (4)
C21B—C22B—H22F109.5C5E—C6E—H6E119.4
H22D—C22B—H22F109.5C1E—C6E—H6E119.4
H22E—C22B—H22F109.5C1E—C11E—C12E119.7 (4)
C13B—O11B—H1B109.5C1E—C11E—C12D116.4 (4)
C2B—O21B—C21B118.3C12E—C11E—C12D90.3 (3)
C6C—C1C—C2C117.7 (3)C1E—C11E—H11E109.7
C6C—C1C—C11C122.3 (2)C12E—C11E—H11E109.7
C2C—C1C—C11C120.0 (2)C12D—C11E—H11E109.7
O21C—C2C—C3C123.2 (2)C13E—C12E—C11E115.9 (4)
O21C—C2C—C1C116.4 (2)C13E—C12E—C11D111.5 (3)
C3C—C2C—C1C120.5 (3)C11E—C12E—C11D89.7 (3)
C4C—C3C—C2C119.7 (3)C13E—C12E—H12E112.6
C4C—C3C—H3C120.1C11E—C12E—H12E112.6
C2C—C3C—H3C120.1C11D—C12E—H12E112.6
C5C—C4C—C3C121.1 (3)O12E—C13E—O11E124.3 (4)
C5C—C4C—H4C119.4O12E—C13E—C12E122.4 (3)
C3C—C4C—H4C119.4O11E—C13E—C12E112.6 (3)
C4C—C5C—C6C118.9 (3)O21E—C21E—C22E107.5 (3)
C4C—C5C—H5C120.5O21E—C21E—H21I110.2
C6C—C5C—H5C120.5C22E—C21E—H21I110.2
C5C—C6C—C1C122.0 (3)O21E—C21E—H21J110.2
C5C—C6C—H6C119.0C22E—C21E—H21J110.2
C1C—C6C—H6C119.0H21I—C21E—H21J108.5
C12C—C11C—C1C126.0 (3)C13E—O11E—H1E109.5
C12C—C11C—H11C117.0C2E—O21E—C21E117.7 (3)
C1C—C11C—H11C117.0
C6A—C1A—C2A—O21A179.8C6D—C1D—C2D—C3D0.2 (6)
C11A—C1A—C2A—O21A3.3C11D—C1D—C2D—C3D171.2 (4)
C6A—C1A—C2A—C3A1.6O21D—C2D—C3D—C4D179.6 (4)
C11A—C1A—C2A—C3A178.1C1D—C2D—C3D—C4D0.1 (6)
O21A—C2A—C3A—C4A179.9C2D—C3D—C4D—C5D0.7 (6)
C1A—C2A—C3A—C4A1.6C3D—C4D—C5D—C6D1.5 (7)
C2A—C3A—C4A—C5A0.6C4D—C5D—C6D—C1D1.6 (7)
C3A—C4A—C5A—C6A0.3C2D—C1D—C6D—C5D1.0 (6)
C4A—C5A—C6A—C1A0.2C11D—C1D—C6D—C5D171.3 (5)
C2A—C1A—C6A—C5A0.7C6D—C1D—C11D—C12D14.0 (6)
C11A—C1A—C6A—C5A177.2C2D—C1D—C11D—C12D175.6 (4)
C6A—C1A—C11A—C12A0.1C6D—C1D—C11D—C12E92.3 (5)
C2A—C1A—C11A—C12A176.3C2D—C1D—C11D—C12E78.0 (5)
C1A—C11A—C12A—C13A179.9C1D—C11D—C12D—C13D125.0 (4)
C11A—C12A—C13A—O12A0.5C12E—C11D—C12D—C13D114.0 (4)
C11A—C12A—C13A—O11A179.6C1D—C11D—C12D—C11E120.2 (4)
C3A—C2A—O21A—C21A1.1C12E—C11D—C12D—C11E0.8 (3)
C1A—C2A—O21A—C21A177.4C11D—C12D—C13D—O12D31.2 (6)
C22A—C21A—O21A—C2A175.5C11E—C12D—C13D—O12D70.1 (5)
C6B—C1B—C2B—O21B179.7C11D—C12D—C13D—O11D158.0 (3)
C11B—C1B—C2B—O21B2.6C11E—C12D—C13D—O11D100.8 (4)
C6B—C1B—C2B—C3B0.1C1D—C2D—O21D—C21D169.0 (4)
C11B—C1B—C2B—C3B177.0C3D—C2D—O21D—C21D11.4 (6)
O21B—C2B—C3B—C4B179.6C22D—C21D—O21D—C2D174.4 (3)
C1B—C2B—C3B—C4B0.1C6E—C1E—C2E—O21E179.0 (3)
C2B—C3B—C4B—C5B0.2C11E—C1E—C2E—O21E11.2 (5)
C3B—C4B—C5B—C6B0.3C6E—C1E—C2E—C3E0.6 (6)
C4B—C5B—C6B—C1B0.3C11E—C1E—C2E—C3E169.2 (4)
C2B—C1B—C6B—C5B0.1O21E—C2E—C3E—C4E178.3 (4)
C11B—C1B—C6B—C5B177.2C1E—C2E—C3E—C4E1.3 (7)
C6B—C1B—C11B—C12B8.9C2E—C3E—C4E—C5E0.6 (7)
C2B—C1B—C11B—C12B174.1C3E—C4E—C5E—C6E0.6 (7)
C1B—C11B—C12B—C13B179.5C4E—C5E—C6E—C1E1.3 (7)
C11B—C12B—C13B—O12B6.2C2E—C1E—C6E—C5E0.7 (6)
C11B—C12B—C13B—O11B173.4C11E—C1E—C6E—C5E169.6 (5)
C3B—C2B—O21B—C21B3.4C6E—C1E—C11E—C12E7.9 (6)
C1B—C2B—O21B—C21B177.0C2E—C1E—C11E—C12E177.0 (4)
C22B—C21B—O21B—C2B175.8C6E—C1E—C11E—C12D98.9 (5)
C6C—C1C—C2C—O21C177.4 (3)C2E—C1E—C11E—C12D70.2 (5)
C11C—C1C—C2C—O21C4.1 (4)C13D—C12D—C11E—C1E7.2 (5)
C6C—C1C—C2C—C3C3.2 (5)C11D—C12D—C11E—C1E124.6 (4)
C11C—C1C—C2C—C3C175.3 (3)C13D—C12D—C11E—C12E116.6 (3)
O21C—C2C—C3C—C4C178.5 (3)C11D—C12D—C11E—C12E0.9 (3)
C1C—C2C—C3C—C4C2.2 (5)C1E—C11E—C12E—C13E124.4 (4)
C2C—C3C—C4C—C5C0.0 (6)C12D—C11E—C12E—C13E114.7 (4)
C3C—C4C—C5C—C6C1.1 (6)C1E—C11E—C12E—C11D121.8 (4)
C4C—C5C—C6C—C1C0.0 (5)C12D—C11E—C12E—C11D0.8 (3)
C2C—C1C—C6C—C5C2.1 (5)C1D—C11D—C12E—C13E4.6 (5)
C11C—C1C—C6C—C5C176.3 (3)C12D—C11D—C12E—C13E118.7 (3)
C6C—C1C—C11C—C12C3.1 (5)C1D—C11D—C12E—C11E122.4 (4)
C2C—C1C—C11C—C12C175.3 (3)C12D—C11D—C12E—C11E0.9 (3)
C1C—C11C—C12C—C13C176.3 (3)C11E—C12E—C13E—O12E22.7 (6)
C11C—C12C—C13C—O12C6.0 (5)C11D—C12E—C13E—O12E77.9 (5)
C11C—C12C—C13C—O11C173.4 (3)C11E—C12E—C13E—O11E166.4 (3)
C3C—C2C—O21C—C21C3.5 (4)C11D—C12E—C13E—O11E93.0 (4)
C1C—C2C—O21C—C21C177.1 (2)C1E—C2E—O21E—C21E165.6 (3)
C22C—C21C—O21C—C2C179.6 (2)C3E—C2E—O21E—C21E14.8 (5)
C6D—C1D—C2D—O21D179.8 (3)C22E—C21E—O21E—C2E171.6 (3)
C11D—C1D—C2D—O21D9.2 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11A—H1A···O12Ai0.841.632.429 (8)158
O11B—H1B···O12Cii0.841.702.522 (5)167
O11C—H1C···O12Bii0.841.772.603 (5)171
O11E—H1E···O12Cii0.841.872.686 (3)164
O11C—H1C···O12Eii0.841.852.685 (4)171
O11D—H1D···O12Di0.842.052.798 (5)148
O11D—H1D···O12Ai0.842.022.727 (5)141
O11A—H1A···O12Di0.841.632.453 (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 = 576.62F(000) = 612
Triclinic, P1Dx = 1.301 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3863 (13) ÅCell parameters from 1002 reflections
b = 10.9711 (18) Åθ = 2.6–27.0°
c = 17.427 (3) ŵ = 0.09 mm1
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 tubeRint = 0.028
Graphite monochromatorθmax = 25.5°, θmin = 1.2°
phi and ω scansh = 1010
8385 measured reflectionsk = 137
5439 independent reflectionsl = 2119
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H 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 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
0.912(C22H24O6)·1.176(C11H12O3)γ = 111.336 (3)°
Mr = 576.62V = 1471.6 (4) Å3
Triclinic, P1Z = 2
a = 8.3863 (13) ÅMo Kα radiation
b = 10.9711 (18) ŵ = 0.09 mm1
c = 17.427 (3) ÅT = 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 reflectionsRint = 0.028
5439 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.140H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.19 e Å3
5439 reflectionsΔρmin = 0.26 e Å3
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
xyzUiso*/UeqOcc. (<1)
C1A1.0137 (14)0.0190 (11)0.2217 (7)0.045 (3)*0.088 (3)
C2A1.0055 (14)0.0165 (11)0.3016 (7)0.045 (3)*0.088 (3)
C3A1.1474 (14)0.0252 (11)0.3475 (7)0.045 (3)*0.088 (3)
H3A1.14210.02570.40190.054*0.088 (3)
C4A1.2966 (14)0.0331 (11)0.3144 (7)0.045 (3)*0.088 (3)
H4A1.39390.03830.34610.054*0.088 (3)
C5A1.3067 (14)0.0338 (11)0.2359 (7)0.045 (3)*0.088 (3)
H5A1.41020.03880.21340.054*0.088 (3)
C6A1.1674 (14)0.0270 (11)0.1905 (7)0.045 (3)*0.088 (3)
H6A1.17530.02780.13630.054*0.088 (3)
C11A0.8605 (14)0.0056 (11)0.1713 (7)0.024 (6)*0.088 (3)
H11A0.76090.00100.19720.029*0.088 (3)
C12A0.8448 (14)0.0007 (11)0.0940 (7)0.016 (5)*0.088 (3)
H12A0.94140.00340.06590.019*0.088 (3)
C13A0.6856 (14)0.0137 (11)0.0512 (7)0.045 (3)*0.088 (3)
C21A0.8378 (14)0.0107 (11)0.4119 (7)0.045 (3)*0.088 (3)
H21A0.92810.09120.44180.054*0.088 (3)
H21B0.85110.06830.42780.054*0.088 (3)
C22A0.6637 (14)0.0114 (11)0.4270 (7)0.045 (3)*0.088 (3)
H22A0.64910.01310.48260.068*0.088 (3)
H22B0.57550.06870.39710.068*0.088 (3)
H22C0.65220.09010.41110.068*0.088 (3)
O11A0.6837 (14)0.0182 (11)0.0221 (7)0.045 (3)*0.088 (3)
H1A0.58600.02570.04030.068*0.088 (3)
O12A0.5587 (14)0.0199 (11)0.0899 (7)0.045 (3)*0.088 (3)
O21A0.8525 (14)0.0081 (11)0.3298 (7)0.045 (3)*0.088 (3)
C1B0.7657 (16)0.3289 (12)0.1256 (7)0.045 (3)*0.088 (3)
C2B0.7669 (16)0.3147 (12)0.0443 (7)0.045 (3)*0.088 (3)
C3B0.6277 (16)0.3116 (12)0.0017 (7)0.045 (3)*0.088 (3)
H3B0.62930.30200.05670.054*0.088 (3)
C4B0.4867 (16)0.3223 (12)0.0326 (7)0.045 (3)*0.088 (3)
H4B0.39120.32040.00090.054*0.088 (3)
C5B0.4822 (16)0.3359 (12)0.1122 (7)0.045 (3)*0.088 (3)
H5B0.38420.34280.13550.054*0.088 (3)
C6B0.6215 (16)0.3394 (12)0.1578 (7)0.045 (3)*0.088 (3)
H6B0.61850.34920.21280.054*0.088 (3)
C11B0.9158 (16)0.3389 (12)0.1755 (7)0.016 (6)*0.088 (3)
H11B1.01620.34380.15020.020*0.088 (3)
C12B0.9274 (16)0.3418 (12)0.2527 (7)0.013 (5)*0.088 (3)
H12B0.83000.33780.28010.016*0.088 (3)
C13B1.0839 (16)0.3509 (12)0.2962 (7)0.045 (3)*0.088 (3)
C21B0.9159 (16)0.2843 (12)0.0679 (7)0.045 (3)*0.088 (3)
H21C0.90920.36110.08950.054*0.088 (3)
H21D0.81740.20370.09220.054*0.088 (3)
C22B1.0817 (16)0.2678 (12)0.0842 (7)0.045 (3)*0.088 (3)
H22D1.08890.25310.14060.068*0.088 (3)
H22E1.08670.19150.06260.068*0.088 (3)
H22F1.17810.34820.06000.068*0.088 (3)
O11B1.0706 (16)0.3395 (12)0.3686 (7)0.045 (3)*0.088 (3)
H1B1.16570.34580.38930.068*0.088 (3)
O12B1.2199 (16)0.3680 (12)0.2627 (7)0.045 (3)*0.088 (3)
O21B0.9117 (16)0.3054 (12)0.0150 (7)0.045 (3)*0.088 (3)
C1C0.2223 (3)0.6536 (2)0.42299 (12)0.0314 (6)
C2C0.2244 (3)0.6470 (2)0.34199 (13)0.0348 (6)
C3C0.0739 (3)0.6236 (3)0.29572 (14)0.0488 (7)
H3C0.07450.61440.24070.059*
C4C0.0752 (3)0.6137 (3)0.32968 (15)0.0555 (8)
H4C0.17710.59740.29780.067*
C5C0.0786 (3)0.6272 (3)0.40957 (15)0.0486 (7)
H5C0.18080.62370.43280.058*
C6C0.0689 (3)0.6460 (2)0.45519 (14)0.0381 (6)
H6C0.06600.65400.51010.046*
C11C0.3734 (3)0.6618 (2)0.47051 (12)0.0312 (6)
H11C0.47410.67040.44470.037*
C12C0.3839 (3)0.6584 (2)0.54665 (13)0.0370 (6)
H12C0.28870.65750.57500.044*
C13C0.5366 (3)0.6559 (2)0.58789 (13)0.0358 (6)
C21C0.3890 (3)0.6673 (3)0.23126 (12)0.0404 (6)
H21E0.35470.73930.21740.048*
H21F0.31130.58210.20020.048*
C22C0.5712 (3)0.6925 (3)0.21517 (13)0.0469 (7)
H22G0.64780.77220.25010.070*
H22H0.58570.70570.16100.070*
H22I0.59970.61620.22380.070*
O11C0.51355 (19)0.63430 (18)0.65987 (9)0.0530 (5)
H1C0.60430.63310.68100.080*
O12C0.6715 (2)0.66913 (17)0.55821 (8)0.0439 (5)
O21C0.37849 (18)0.66266 (17)0.31313 (8)0.0388 (4)
C1D1.0117 (3)0.0381 (2)0.23083 (14)0.0290 (6)0.912 (3)
C2D0.9942 (3)0.0037 (3)0.30312 (14)0.0298 (6)0.912 (3)
C3D1.1228 (3)0.0346 (3)0.33792 (15)0.0412 (8)0.912 (3)
H3D1.11050.06240.38730.049*0.912 (3)
C4D1.2683 (3)0.0248 (3)0.30058 (16)0.0447 (8)0.912 (3)
H4D1.35600.04610.32440.054*0.912 (3)
C5D1.2880 (4)0.0155 (3)0.22913 (16)0.0413 (7)0.912 (3)
H5D1.38840.02160.20360.050*0.912 (3)
C6D1.1600 (3)0.0472 (3)0.19473 (15)0.0351 (7)0.912 (3)
H6D1.17400.07570.14560.042*0.912 (3)
C11D0.8753 (3)0.0841 (3)0.20037 (13)0.0319 (6)0.912 (3)
H11D0.75850.02100.20820.038*0.912 (3)
C12D0.8773 (3)0.1158 (2)0.11698 (13)0.0325 (7)0.912 (3)
H12D0.97940.10990.09100.039*0.912 (3)
C13D0.7111 (3)0.0426 (3)0.06600 (13)0.0293 (6)0.912 (3)
C21D0.8345 (3)0.0253 (3)0.41589 (14)0.0417 (7)0.912 (3)
H21G0.93320.04470.44850.050*0.912 (3)
H21H0.83680.11280.42250.050*0.912 (3)
C22D0.6696 (3)0.0150 (3)0.43987 (15)0.0428 (7)0.912 (3)
H22J0.66970.07260.43420.064*0.912 (3)
H22K0.65810.02700.49430.064*0.912 (3)
H22L0.57290.08400.40680.064*0.912 (3)
O11D0.7303 (2)0.0347 (2)0.00935 (9)0.0390 (5)0.912 (3)
H1D0.63530.01090.03480.059*0.912 (3)
O12D0.5711 (2)0.0068 (2)0.09141 (10)0.0362 (5)0.912 (3)
O21D0.8454 (2)0.0097 (2)0.33606 (10)0.0333 (5)0.912 (3)
C1E0.7681 (3)0.3129 (3)0.11991 (14)0.0305 (6)0.912 (3)
C2E0.7770 (3)0.3377 (3)0.04359 (14)0.0303 (6)0.912 (3)
C3E0.6464 (3)0.3634 (3)0.00652 (15)0.0420 (8)0.912 (3)
H3E0.65290.37940.04570.050*0.912 (3)
C4E0.5075 (3)0.3656 (3)0.04598 (17)0.0452 (8)0.912 (3)
H4E0.41690.38100.02020.054*0.912 (3)
C5E0.4977 (4)0.3459 (3)0.12222 (17)0.0419 (7)0.912 (3)
H5E0.40330.35040.14960.050*0.912 (3)
C6E0.6289 (3)0.3192 (3)0.15836 (16)0.0381 (7)0.912 (3)
H6E0.62270.30500.21080.046*0.912 (3)
C11E0.9009 (3)0.2651 (3)0.15133 (13)0.0316 (6)0.912 (3)
H11E1.01890.32680.14400.038*0.912 (3)
C12E0.8958 (3)0.2327 (3)0.23490 (13)0.0321 (7)0.912 (3)
H12E0.79220.23740.26010.038*0.912 (3)
C13E1.0594 (3)0.3035 (3)0.28721 (14)0.0290 (6)0.912 (3)
C21E0.9162 (3)0.3193 (3)0.07374 (14)0.0387 (7)0.912 (3)
H21I0.91710.40170.09090.046*0.912 (3)
H21J0.81020.24510.09790.046*0.912 (3)
C22E1.0718 (4)0.2918 (3)0.09773 (16)0.0487 (8)0.912 (3)
H22M1.17580.36890.07710.073*0.912 (3)
H22N1.06700.27450.15470.073*0.912 (3)
H22O1.07420.21400.07700.073*0.912 (3)
O11E1.0387 (2)0.2971 (2)0.36085 (9)0.0364 (5)0.912 (3)
H1E1.13530.32430.38630.055*0.912 (3)
O12E1.1990 (3)0.3515 (2)0.26216 (11)0.0351 (5)0.912 (3)
O21E0.9211 (2)0.3334 (2)0.00973 (10)0.0359 (5)0.912 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1C0.0349 (13)0.0308 (14)0.0286 (13)0.0123 (11)0.0033 (10)0.0049 (10)
C2C0.0307 (13)0.0448 (16)0.0325 (14)0.0181 (12)0.0036 (11)0.0072 (11)
C3C0.0418 (15)0.080 (2)0.0328 (15)0.0302 (15)0.0038 (12)0.0164 (14)
C4C0.0403 (16)0.092 (2)0.0491 (17)0.0371 (16)0.0049 (13)0.0237 (16)
C5C0.0381 (15)0.067 (2)0.0519 (17)0.0278 (15)0.0147 (13)0.0219 (15)
C6C0.0404 (14)0.0432 (16)0.0347 (14)0.0196 (13)0.0062 (11)0.0081 (12)
C11C0.0315 (13)0.0322 (14)0.0295 (13)0.0119 (11)0.0029 (10)0.0034 (10)
C12C0.0347 (14)0.0459 (17)0.0295 (14)0.0146 (13)0.0021 (11)0.0047 (11)
C13C0.0394 (15)0.0394 (16)0.0248 (13)0.0111 (13)0.0001 (11)0.0040 (11)
C21C0.0427 (15)0.0586 (18)0.0255 (13)0.0239 (14)0.0046 (11)0.0106 (12)
C22C0.0371 (14)0.0638 (19)0.0337 (14)0.0135 (14)0.0026 (11)0.0037 (13)
O11C0.0392 (10)0.0894 (15)0.0296 (10)0.0196 (10)0.0003 (8)0.0199 (10)
O12C0.0414 (10)0.0648 (13)0.0263 (9)0.0219 (9)0.0017 (8)0.0043 (8)
O21C0.0320 (9)0.0614 (12)0.0269 (9)0.0207 (9)0.0016 (7)0.0110 (8)
C1D0.0285 (14)0.0277 (15)0.0292 (14)0.0089 (12)0.0019 (11)0.0050 (11)
C2D0.0310 (14)0.0288 (15)0.0287 (14)0.0105 (12)0.0018 (11)0.0046 (11)
C3D0.0462 (17)0.052 (2)0.0322 (16)0.0262 (16)0.0050 (13)0.0106 (14)
C4D0.0404 (17)0.054 (2)0.0488 (19)0.0305 (16)0.0042 (14)0.0044 (16)
C5D0.0344 (16)0.054 (2)0.0397 (17)0.0236 (15)0.0002 (13)0.0012 (14)
C6D0.0332 (15)0.0424 (18)0.0313 (15)0.0162 (14)0.0024 (12)0.0058 (13)
C11D0.0295 (14)0.0384 (17)0.0291 (14)0.0134 (13)0.0002 (11)0.0087 (12)
C12D0.0294 (14)0.0447 (18)0.0266 (14)0.0187 (13)0.0008 (11)0.0034 (12)
C13D0.0367 (16)0.0339 (17)0.0215 (14)0.0171 (13)0.0038 (12)0.0063 (11)
C21D0.0450 (17)0.057 (2)0.0286 (15)0.0236 (16)0.0003 (12)0.0124 (14)
C22D0.0464 (17)0.056 (2)0.0307 (15)0.0239 (16)0.0031 (13)0.0105 (14)
O11D0.0359 (11)0.0530 (14)0.0224 (10)0.0115 (11)0.0012 (8)0.0027 (9)
O12D0.0335 (10)0.0431 (12)0.0272 (10)0.0090 (9)0.0006 (8)0.0055 (9)
O21D0.0298 (10)0.0493 (12)0.0240 (10)0.0161 (9)0.0014 (7)0.0129 (8)
C1E0.0302 (14)0.0327 (16)0.0301 (15)0.0134 (13)0.0007 (11)0.0065 (12)
C2E0.0305 (14)0.0295 (16)0.0299 (14)0.0106 (12)0.0008 (11)0.0044 (12)
C3E0.0453 (17)0.057 (2)0.0303 (15)0.0265 (16)0.0054 (13)0.0123 (14)
C4E0.0423 (17)0.054 (2)0.0504 (19)0.0289 (16)0.0058 (14)0.0147 (16)
C5E0.0372 (16)0.0492 (19)0.0469 (18)0.0244 (15)0.0029 (13)0.0099 (14)
C6E0.0394 (16)0.0451 (19)0.0314 (15)0.0171 (14)0.0021 (12)0.0083 (13)
C11E0.0293 (14)0.0382 (18)0.0257 (14)0.0110 (13)0.0001 (11)0.0051 (13)
C12E0.0303 (14)0.0451 (18)0.0249 (14)0.0190 (13)0.0005 (11)0.0059 (12)
C13E0.0390 (16)0.0316 (17)0.0208 (14)0.0193 (14)0.0009 (12)0.0020 (11)
C21E0.0428 (16)0.053 (2)0.0236 (14)0.0205 (15)0.0011 (12)0.0091 (13)
C22E0.0507 (18)0.063 (2)0.0347 (17)0.0243 (17)0.0055 (14)0.0075 (15)
O11E0.0393 (11)0.0515 (13)0.0186 (9)0.0197 (10)0.0030 (8)0.0009 (9)
O12E0.0356 (11)0.0392 (12)0.0268 (10)0.0106 (9)0.0013 (8)0.0044 (8)
O21E0.0362 (10)0.0516 (13)0.0248 (10)0.0206 (10)0.0009 (8)0.0105 (9)
Geometric parameters (Å, º) top
C1A—C6A1.3930C12C—C13C1.459 (3)
C1A—C2A1.4008C12C—H12C0.9500
C1A—C11A1.4821C13C—O12C1.228 (2)
C2A—O21A1.3649C13C—O11C1.317 (2)
C2A—C3A1.3788C21C—O21C1.440 (2)
C3A—C4A1.3737C21C—C22C1.495 (3)
C3A—H3A0.9500C21C—H21E0.9900
C4A—C5A1.3750C21C—H21F0.9900
C4A—H4A0.9500C22C—H22G0.9800
C5A—C6A1.3631C22C—H22H0.9800
C5A—H5A0.9500C22C—H22I0.9800
C6A—H6A0.9500O11C—H1C0.8400
C11A—C12A1.3389C1D—C6D1.389 (3)
C11A—H11A0.9500C1D—C2D1.396 (3)
C12A—C13A1.4585C1D—C11D1.517 (3)
C12A—H12A0.9500C2D—O21D1.374 (3)
C13A—O12A1.2635C2D—C3D1.390 (3)
C13A—O11A1.2715C3D—C4D1.378 (3)
C21A—O21A1.4363C3D—H3D0.9500
C21A—C22A1.4941C4D—C5D1.376 (3)
C21A—H21A0.9900C4D—H4D0.9500
C21A—H21B0.9900C5D—C6D1.387 (3)
C22A—H22A0.9800C5D—H5D0.9500
C22A—H22B0.9800C6D—H6D0.9500
C22A—H22C0.9800C11D—C12D1.542 (3)
O11A—H1A0.8400C11D—C12E1.599 (4)
C1B—C6B1.3842C11D—H11D1.0000
C1B—C2B1.4043C12D—C13D1.509 (3)
C1B—C11B1.4677C12D—C11E1.598 (4)
C2B—O21B1.3643C12D—H12D1.0000
C2B—C3B1.3827C13D—O12D1.215 (3)
C3B—C4B1.3764C13D—O11D1.322 (3)
C3B—H3B0.9500C21D—O21D1.428 (3)
C4B—C5B1.3784C21D—C22D1.496 (3)
C4B—H4B0.9500C21D—H21G0.9900
C5B—C6B1.3773C21D—H21H0.9900
C5B—H5B0.9500C22D—H22J0.9800
C6B—H6B0.9500C22D—H22K0.9800
C11B—C12B1.3405C22D—H22L0.9800
C11B—H11B0.9500O11D—H1D0.8400
C12B—C13B1.4590C1E—C6E1.383 (3)
C12B—H12B0.9500C1E—C2E1.395 (3)
C13B—O12B1.2632C1E—C11E1.512 (3)
C13B—O11B1.2893C2E—O21E1.374 (3)
C21B—O21B1.4331C2E—C3E1.389 (3)
C21B—C22B1.4961C3E—C4E1.377 (3)
C21B—H21C0.9900C3E—H3E0.9500
C21B—H21D0.9900C4E—C5E1.377 (3)
C22B—H22D0.9800C4E—H4E0.9500
C22B—H22E0.9800C5E—C6E1.392 (3)
C22B—H22F0.9800C5E—H5E0.9500
O11B—H1B0.8400C6E—H6E0.9500
C1C—C6C1.399 (3)C11E—C12E1.547 (3)
C1C—C2C1.404 (3)C11E—H11E1.0000
C1C—C11C1.459 (3)C12E—C13E1.502 (3)
C2C—O21C1.362 (2)C12E—H12E1.0000
C2C—C3C1.396 (3)C13E—O12E1.221 (3)
C3C—C4C1.375 (3)C13E—O11E1.309 (3)
C3C—H3C0.9500C21E—O21E1.438 (3)
C4C—C5C1.381 (3)C21E—C22E1.501 (3)
C4C—H4C0.9500C21E—H21I0.9900
C5C—C6C1.382 (3)C21E—H21J0.9900
C5C—H5C0.9500C22E—H22M0.9800
C6C—H6C0.9500C22E—H22N0.9800
C11C—C12C1.334 (3)C22E—H22O0.9800
C11C—H11C0.9500O11E—H1E0.8400
C6A—C1A—C2A117.9C11C—C12C—C13C122.3 (2)
C6A—C1A—C11A121.2C11C—C12C—H12C118.9
C2A—C1A—C11A120.9C13C—C12C—H12C118.9
O21A—C2A—C3A123.6O12C—C13C—O11C123.3 (2)
O21A—C2A—C1A116.0O12C—C13C—C12C123.7 (2)
C3A—C2A—C1A120.4O11C—C13C—C12C113.0 (2)
C4A—C3A—C2A119.9O21C—C21C—C22C107.31 (18)
C4A—C3A—H3A120.1O21C—C21C—H21E110.3
C2A—C3A—H3A120.1C22C—C21C—H21E110.3
C3A—C4A—C5A120.7O21C—C21C—H21F110.3
C3A—C4A—H4A119.7C22C—C21C—H21F110.3
C5A—C4A—H4A119.7H21E—C21C—H21F108.5
C6A—C5A—C4A119.6C21C—C22C—H22G109.5
C6A—C5A—H5A120.2C21C—C22C—H22H109.5
C4A—C5A—H5A120.2H22G—C22C—H22H109.5
C5A—C6A—C1A121.6C21C—C22C—H22I109.5
C5A—C6A—H6A119.2H22G—C22C—H22I109.5
C1A—C6A—H6A119.2H22H—C22C—H22I109.5
C12A—C11A—C1A128.2C13C—O11C—H1C109.5
C12A—C11A—H11A115.9C2C—O21C—C21C117.62 (16)
C1A—C11A—H11A115.9C6D—C1D—C2D118.3 (2)
C11A—C12A—C13A122.7C6D—C1D—C11D123.8 (2)
C11A—C12A—H12A118.7C2D—C1D—C11D117.6 (2)
C13A—C12A—H12A118.7O21D—C2D—C3D123.9 (2)
O12A—C13A—O11A124.5O21D—C2D—C1D115.6 (2)
O12A—C13A—C12A117.5C3D—C2D—C1D120.5 (2)
O11A—C13A—C12A118.0C4D—C3D—C2D119.8 (2)
O21A—C21A—C22A107.2C4D—C3D—H3D120.1
O21A—C21A—H21A110.3C2D—C3D—H3D120.1
C22A—C21A—H21A110.3C5D—C4D—C3D120.7 (3)
O21A—C21A—H21B110.3C5D—C4D—H4D119.6
C22A—C21A—H21B110.3C3D—C4D—H4D119.6
H21A—C21A—H21B108.5C4D—C5D—C6D119.4 (3)
C21A—C22A—H22A109.5C4D—C5D—H5D120.3
C21A—C22A—H22B109.5C6D—C5D—H5D120.3
H22A—C22A—H22B109.5C5D—C6D—C1D121.2 (2)
C21A—C22A—H22C109.5C5D—C6D—H6D119.4
H22A—C22A—H22C109.5C1D—C6D—H6D119.4
H22B—C22A—H22C109.5C1D—C11D—C12D119.5 (2)
C13A—O11A—H1A109.5C1D—C11D—C12E115.9 (2)
C2A—O21A—C21A118.8C12D—C11D—C12E90.37 (18)
C6B—C1B—C2B118.0C1D—C11D—H11D109.9
C6B—C1B—C11B120.8C12D—C11D—H11D109.9
C2B—C1B—C11B121.2C12E—C11D—H11D109.9
O21B—C2B—C3B123.3C13D—C12D—C11D115.0 (2)
O21B—C2B—C1B116.1C13D—C12D—C11E112.5 (2)
C3B—C2B—C1B120.6C11D—C12D—C11E89.80 (17)
C4B—C3B—C2B119.6C13D—C12D—H12D112.6
C4B—C3B—H3B120.2C11D—C12D—H12D112.6
C2B—C3B—H3B120.2C11E—C12D—H12D112.6
C3B—C4B—C5B120.9O12D—C13D—O11D122.8 (2)
C3B—C4B—H4B119.6O12D—C13D—C12D123.2 (2)
C5B—C4B—H4B119.6O11D—C13D—C12D113.6 (2)
C6B—C5B—C4B119.2O21D—C21D—C22D107.9 (2)
C6B—C5B—H5B120.4O21D—C21D—H21G110.1
C4B—C5B—H5B120.4C22D—C21D—H21G110.1
C5B—C6B—C1B121.7O21D—C21D—H21H110.1
C5B—C6B—H6B119.1C22D—C21D—H21H110.1
C1B—C6B—H6B119.1H21G—C21D—H21H108.4
C12B—C11B—C1B127.4C13D—O11D—H1D109.5
C12B—C11B—H11B116.3C2D—O21D—C21D118.24 (18)
C1B—C11B—H11B116.3C6E—C1E—C2E118.1 (2)
C11B—C12B—C13B122.5C6E—C1E—C11E124.3 (2)
C11B—C12B—H12B118.7C2E—C1E—C11E117.1 (2)
C13B—C12B—H12B118.7O21E—C2E—C3E124.2 (2)
O12B—C13B—O11B124.4O21E—C2E—C1E115.0 (2)
O12B—C13B—C12B120.1C3E—C2E—C1E120.8 (2)
O11B—C13B—C12B115.4C4E—C3E—C2E119.5 (2)
O21B—C21B—C22B107.2C4E—C3E—H3E120.3
O21B—C21B—H21C110.3C2E—C3E—H3E120.3
C22B—C21B—H21C110.3C5E—C4E—C3E121.2 (2)
O21B—C21B—H21D110.3C5E—C4E—H4E119.4
C22B—C21B—H21D110.3C3E—C4E—H4E119.4
H21C—C21B—H21D108.5C4E—C5E—C6E118.7 (3)
C21B—C22B—H22D109.5C4E—C5E—H5E120.7
C21B—C22B—H22E109.5C6E—C5E—H5E120.7
H22D—C22B—H22E109.5C1E—C6E—C5E121.8 (2)
C21B—C22B—H22F109.5C1E—C6E—H6E119.1
H22D—C22B—H22F109.5C5E—C6E—H6E119.1
H22E—C22B—H22F109.5C1E—C11E—C12E119.8 (2)
C13B—O11B—H1B109.5C1E—C11E—C12D115.7 (2)
C2B—O21B—C21B118.3C12E—C11E—C12D90.21 (18)
C6C—C1C—C2C117.6 (2)C1E—C11E—H11E109.9
C6C—C1C—C11C121.9 (2)C12E—C11E—H11E109.9
C2C—C1C—C11C120.4 (2)C12D—C11E—H11E109.9
O21C—C2C—C3C123.7 (2)C13E—C12E—C11E115.6 (2)
O21C—C2C—C1C116.09 (19)C13E—C12E—C11D111.38 (19)
C3C—C2C—C1C120.2 (2)C11E—C12E—C11D89.61 (17)
C4C—C3C—C2C120.1 (2)C13E—C12E—H12E112.8
C4C—C3C—H3C119.9C11E—C12E—H12E112.8
C2C—C3C—H3C119.9C11D—C12E—H12E112.8
C3C—C4C—C5C120.9 (2)O12E—C13E—O11E123.8 (2)
C3C—C4C—H4C119.6O12E—C13E—C12E122.6 (2)
C5C—C4C—H4C119.6O11E—C13E—C12E113.2 (2)
C4C—C5C—C6C119.0 (2)O21E—C21E—C22E107.72 (19)
C4C—C5C—H5C120.5O21E—C21E—H21I110.2
C6C—C5C—H5C120.5C22E—C21E—H21I110.2
C5C—C6C—C1C122.0 (2)O21E—C21E—H21J110.2
C5C—C6C—H6C119.0C22E—C21E—H21J110.2
C1C—C6C—H6C119.0H21I—C21E—H21J108.5
C12C—C11C—C1C126.3 (2)C13E—O11E—H1E109.5
C12C—C11C—H11C116.8C2E—O21E—C21E117.59 (18)
C1C—C11C—H11C116.8
C6A—C1A—C2A—O21A179.8C6D—C1D—C2D—C3D0.3 (4)
C11A—C1A—C2A—O21A3.3C11D—C1D—C2D—C3D173.7 (2)
C6A—C1A—C2A—C3A1.6O21D—C2D—C3D—C4D179.6 (2)
C11A—C1A—C2A—C3A178.1C1D—C2D—C3D—C4D0.4 (4)
O21A—C2A—C3A—C4A179.9C2D—C3D—C4D—C5D0.1 (4)
C1A—C2A—C3A—C4A1.6C3D—C4D—C5D—C6D0.3 (4)
C2A—C3A—C4A—C5A0.6C4D—C5D—C6D—C1D0.5 (4)
C3A—C4A—C5A—C6A0.3C2D—C1D—C6D—C5D0.1 (4)
C4A—C5A—C6A—C1A0.2C11D—C1D—C6D—C5D173.7 (3)
C2A—C1A—C6A—C5A0.7C6D—C1D—C11D—C12D13.4 (4)
C11A—C1A—C6A—C5A177.2C2D—C1D—C11D—C12D173.0 (2)
C6A—C1A—C11A—C12A0.1C6D—C1D—C11D—C12E93.0 (3)
C2A—C1A—C11A—C12A176.3C2D—C1D—C11D—C12E80.6 (3)
C1A—C11A—C12A—C13A179.9C1D—C11D—C12D—C13D125.7 (2)
C11A—C12A—C13A—O12A0.5C12E—C11D—C12D—C13D114.0 (2)
C11A—C12A—C13A—O11A179.6C1D—C11D—C12D—C11E119.5 (2)
C3A—C2A—O21A—C21A1.1C12E—C11D—C12D—C11E0.89 (17)
C1A—C2A—O21A—C21A177.4C11D—C12D—C13D—O12D29.2 (4)
C22A—C21A—O21A—C2A175.5C11E—C12D—C13D—O12D71.7 (3)
C6B—C1B—C2B—O21B179.7C11D—C12D—C13D—O11D158.2 (2)
C11B—C1B—C2B—O21B2.6C11E—C12D—C13D—O11D100.9 (2)
C6B—C1B—C2B—C3B0.1C3D—C2D—O21D—C21D11.6 (4)
C11B—C1B—C2B—C3B177.0C1D—C2D—O21D—C21D167.5 (2)
O21B—C2B—C3B—C4B179.6C22D—C21D—O21D—C2D174.3 (2)
C1B—C2B—C3B—C4B0.1C6E—C1E—C2E—O21E178.3 (2)
C2B—C3B—C4B—C5B0.2C11E—C1E—C2E—O21E8.8 (3)
C3B—C4B—C5B—C6B0.3C6E—C1E—C2E—C3E2.2 (4)
C4B—C5B—C6B—C1B0.3C11E—C1E—C2E—C3E170.7 (2)
C2B—C1B—C6B—C5B0.1O21E—C2E—C3E—C4E179.9 (2)
C11B—C1B—C6B—C5B177.2C1E—C2E—C3E—C4E0.6 (4)
C6B—C1B—C11B—C12B8.9C2E—C3E—C4E—C5E1.5 (4)
C2B—C1B—C11B—C12B174.1C3E—C4E—C5E—C6E2.0 (4)
C1B—C11B—C12B—C13B179.5C2E—C1E—C6E—C5E1.7 (4)
C11B—C12B—C13B—O12B6.2C11E—C1E—C6E—C5E170.7 (3)
C11B—C12B—C13B—O11B173.4C4E—C5E—C6E—C1E0.4 (4)
C3B—C2B—O21B—C21B3.4C6E—C1E—C11E—C12E6.2 (4)
C1B—C2B—O21B—C21B177.0C2E—C1E—C11E—C12E178.6 (2)
C22B—C21B—O21B—C2B175.8C6E—C1E—C11E—C12D100.1 (3)
C6C—C1C—C2C—O21C176.2 (2)C2E—C1E—C11E—C12D72.4 (3)
C11C—C1C—C2C—O21C6.6 (3)C13D—C12D—C11E—C1E7.3 (3)
C6C—C1C—C2C—C3C4.7 (4)C11D—C12D—C11E—C1E124.5 (2)
C11C—C1C—C2C—C3C172.5 (2)C13D—C12D—C11E—C12E116.2 (2)
O21C—C2C—C3C—C4C177.6 (2)C11D—C12D—C11E—C12E0.92 (18)
C1C—C2C—C3C—C4C3.4 (4)C1E—C11E—C12E—C13E125.4 (3)
C2C—C3C—C4C—C5C0.3 (4)C12D—C11E—C12E—C13E114.5 (2)
C3C—C4C—C5C—C6C2.4 (4)C1E—C11E—C12E—C11D120.9 (2)
C4C—C5C—C6C—C1C0.9 (4)C12D—C11E—C12E—C11D0.88 (17)
C2C—C1C—C6C—C5C2.6 (4)C1D—C11D—C12E—C13E5.0 (3)
C11C—C1C—C6C—C5C174.5 (2)C12D—C11D—C12E—C13E118.4 (2)
C6C—C1C—C11C—C12C2.6 (4)C1D—C11D—C12E—C11E122.4 (2)
C2C—C1C—C11C—C12C174.5 (2)C12D—C11D—C12E—C11E0.91 (18)
C1C—C11C—C12C—C13C174.6 (2)C11E—C12E—C13E—O12E20.7 (3)
C11C—C12C—C13C—O12C7.1 (4)C11D—C12E—C13E—O12E79.6 (3)
C11C—C12C—C13C—O11C171.3 (2)C11E—C12E—C13E—O11E165.4 (2)
C3C—C2C—O21C—C21C5.9 (3)C11D—C12E—C13E—O11E94.3 (2)
C1C—C2C—O21C—C21C175.0 (2)C3E—C2E—O21E—C21E17.2 (4)
C22C—C21C—O21C—C2C176.9 (2)C1E—C2E—O21E—C21E162.2 (2)
C6D—C1D—C2D—O21D179.5 (2)C22E—C21E—O21E—C2E169.7 (2)
C11D—C1D—C2D—O21D5.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11A—H1A···O12Di0.841.662.472 (11)163
O11D—H1D···O12Ai0.842.022.702 (11)138
O11D—H1D···O12Di0.841.982.718 (3)146
O11C—H1C···O12Eii0.841.842.672 (2)172
O11E—H1E···O12Cii0.841.832.648 (2)163
O11C—H1C···O12Bii0.841.752.584 (12)172
O11B—H1B···O12Cii0.841.692.515 (12)167
O11A—H1A···O12Ai0.841.722.51 (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·C11H12O3Z = 2
Mr = 576.62F(000) = 612
Triclinic, P1Dx = 1.304 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3099 (12) ÅCell parameters from 794 reflections
b = 11.0026 (16) Åθ = 2.5–28.1°
c = 17.471 (3) ŵ = 0.10 mm1
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 tubeRint = 0.028
Graphite monochromatorθmax = 25.5°, θmin = 1.2°
phi and ω scansh = 1010
8381 measured reflectionsk = 137
5409 independent reflectionsl = 2119
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H 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 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C22H24O6·C11H12O3γ = 110.392 (3)°
Mr = 576.62V = 1468.1 (4) Å3
Triclinic, P1Z = 2
a = 8.3099 (12) ÅMo Kα radiation
b = 11.0026 (16) ŵ = 0.10 mm1
c = 17.471 (3) ÅT = 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 reflectionsRint = 0.028
5409 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.18 e Å3
5409 reflectionsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
C1C0.2135 (2)0.64754 (18)0.41729 (10)0.0285 (4)
C2C0.2140 (2)0.63657 (18)0.33616 (10)0.0282 (4)
C3C0.0612 (2)0.6078 (2)0.28917 (11)0.0372 (5)
H3C0.06090.59570.23400.045*
C4C0.0896 (2)0.5969 (2)0.32331 (12)0.0399 (5)
H4C0.19370.57650.29120.048*
C5C0.0912 (2)0.6153 (2)0.40344 (12)0.0393 (5)
H5C0.19410.61190.42660.047*
C6C0.0588 (2)0.63878 (19)0.44919 (11)0.0357 (5)
H6C0.05690.64930.50420.043*
C11C0.3682 (2)0.66037 (17)0.46543 (10)0.0294 (4)
H11C0.46940.66830.43980.035*
C12C0.3807 (2)0.66192 (19)0.54180 (11)0.0347 (5)
H12C0.28600.66390.57030.042*
C13C0.5356 (2)0.66068 (19)0.58309 (11)0.0335 (5)
C21C0.3780 (2)0.6567 (2)0.22554 (10)0.0356 (5)
H21E0.33170.72230.21130.043*
H21F0.30860.56870.19410.043*
C22C0.5638 (2)0.6932 (2)0.21001 (11)0.0462 (6)
H22G0.63310.77560.24550.069*
H22H0.57510.70520.15590.069*
H22I0.60450.62250.21850.069*
O11C0.51430 (18)0.64305 (17)0.65539 (8)0.0504 (4)
O12C0.67170 (17)0.67357 (14)0.55422 (7)0.0410 (4)
O21C0.36971 (15)0.65443 (13)0.30720 (7)0.0345 (3)
C1D1.0113 (2)0.03434 (17)0.23138 (10)0.0265 (4)
C2D0.9924 (2)0.01048 (18)0.30228 (10)0.0295 (4)
C3D1.1192 (2)0.0471 (2)0.33565 (11)0.0378 (5)
H3D1.10430.07910.38310.045*
C4D1.2666 (3)0.0364 (2)0.29876 (12)0.0417 (5)
H4D1.35420.05970.32170.050*
C5D1.2886 (2)0.0077 (2)0.22908 (12)0.0392 (5)
H5D1.39010.01430.20400.047*
C6D1.1602 (2)0.04226 (19)0.19620 (11)0.0332 (5)
H6D1.17520.07220.14810.040*
C11D0.8743 (2)0.08014 (18)0.20145 (9)0.0268 (4)
H11D0.75730.01800.20830.032*
C12D0.8767 (2)0.11147 (17)0.11821 (10)0.0271 (4)
H12D0.97940.10460.09220.033*
C13D0.7110 (2)0.04202 (18)0.06647 (10)0.0279 (4)
C21D0.8335 (3)0.0313 (2)0.41481 (10)0.0412 (5)
H21G0.93360.03670.44830.049*
H21H0.83440.11950.41940.049*
C22D0.6688 (3)0.0176 (2)0.43986 (11)0.0463 (6)
H22J0.67060.07080.43640.069*
H22K0.65750.03020.49390.069*
H22L0.57080.08430.40570.069*
O11D0.73184 (17)0.03306 (14)0.00878 (7)0.0375 (4)
O12D0.56985 (15)0.00372 (13)0.09095 (7)0.0347 (3)
O21D0.84324 (15)0.01509 (13)0.33532 (7)0.0336 (3)
C1E0.7655 (2)0.30836 (18)0.12373 (10)0.0274 (4)
C2E0.7772 (2)0.33581 (18)0.04820 (10)0.0301 (4)
C3E0.6466 (2)0.36397 (19)0.01178 (11)0.0384 (5)
H3E0.65420.38140.03970.046*
C4E0.5056 (3)0.3665 (2)0.05080 (12)0.0408 (5)
H4E0.41600.38490.02570.049*
C5E0.4933 (2)0.3427 (2)0.12556 (12)0.0384 (5)
H5E0.39670.34590.15230.046*
C6E0.6242 (2)0.31384 (19)0.16162 (11)0.0342 (5)
H6E0.61600.29760.21330.041*
C11E0.8994 (2)0.25993 (18)0.15495 (10)0.0270 (4)
H11E1.01770.32080.14870.032*
C12E0.8938 (2)0.22830 (18)0.23735 (10)0.0276 (4)
H12E0.78970.23430.26240.033*
C13E1.0573 (2)0.29663 (18)0.29063 (10)0.0272 (4)
C21E0.9170 (2)0.3160 (2)0.06918 (10)0.0371 (5)
H21I0.91830.39850.08510.045*
H21J0.81030.24320.09430.045*
C22E1.0720 (2)0.2861 (2)0.09369 (11)0.0447 (6)
H22M1.17680.36120.07130.067*
H22N1.06790.27040.15080.067*
H22O1.07290.20710.07510.067*
O11E1.03755 (17)0.29178 (13)0.36453 (7)0.0355 (3)
O12E1.19807 (15)0.34447 (12)0.26650 (7)0.0325 (3)
O21E0.92193 (15)0.33064 (13)0.01424 (7)0.0343 (3)
H1D0.625 (3)0.009 (2)0.0368 (13)0.071 (8)*
H1C0.611 (3)0.648 (2)0.6797 (14)0.078 (9)*
H1E1.151 (3)0.317 (2)0.3959 (14)0.086 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1C0.0300 (10)0.0265 (11)0.0292 (11)0.0095 (9)0.0019 (8)0.0075 (8)
C2C0.0291 (10)0.0289 (11)0.0277 (11)0.0118 (9)0.0018 (8)0.0059 (8)
C3C0.0361 (11)0.0459 (13)0.0305 (11)0.0157 (10)0.0027 (9)0.0089 (10)
C4C0.0305 (11)0.0480 (14)0.0432 (13)0.0161 (10)0.0046 (9)0.0119 (10)
C5C0.0319 (11)0.0460 (13)0.0454 (13)0.0181 (10)0.0054 (10)0.0137 (10)
C6C0.0381 (11)0.0394 (12)0.0310 (11)0.0152 (10)0.0049 (9)0.0081 (9)
C11C0.0285 (10)0.0293 (11)0.0278 (11)0.0081 (9)0.0007 (8)0.0043 (8)
C12C0.0301 (11)0.0429 (13)0.0302 (11)0.0118 (10)0.0002 (8)0.0083 (9)
C13C0.0351 (11)0.0376 (12)0.0236 (11)0.0093 (10)0.0010 (9)0.0041 (9)
C21C0.0393 (12)0.0440 (13)0.0251 (11)0.0167 (10)0.0017 (9)0.0075 (9)
C22C0.0408 (12)0.0602 (15)0.0324 (12)0.0125 (12)0.0022 (9)0.0070 (11)
O11C0.0342 (9)0.0872 (13)0.0292 (9)0.0170 (9)0.0018 (7)0.0214 (8)
O12C0.0366 (8)0.0626 (10)0.0257 (7)0.0212 (7)0.0001 (6)0.0072 (7)
O21C0.0310 (7)0.0499 (9)0.0232 (7)0.0147 (7)0.0012 (6)0.0089 (6)
C1D0.0266 (10)0.0240 (10)0.0259 (10)0.0072 (8)0.0032 (8)0.0019 (8)
C2D0.0293 (10)0.0284 (11)0.0287 (10)0.0086 (9)0.0033 (8)0.0046 (8)
C3D0.0417 (12)0.0429 (13)0.0347 (11)0.0208 (10)0.0032 (9)0.0128 (10)
C4D0.0388 (12)0.0484 (14)0.0440 (13)0.0253 (11)0.0064 (10)0.0067 (11)
C5D0.0312 (11)0.0479 (14)0.0415 (12)0.0203 (10)0.0023 (9)0.0042 (10)
C6D0.0349 (11)0.0372 (12)0.0286 (11)0.0153 (10)0.0007 (9)0.0052 (9)
C11D0.0237 (10)0.0340 (11)0.0227 (10)0.0101 (9)0.0006 (8)0.0067 (8)
C12D0.0256 (10)0.0333 (11)0.0244 (10)0.0131 (9)0.0014 (8)0.0052 (8)
C13D0.0310 (11)0.0295 (11)0.0240 (11)0.0120 (9)0.0007 (8)0.0050 (8)
C21D0.0450 (12)0.0564 (14)0.0265 (11)0.0202 (11)0.0005 (9)0.0153 (10)
C22D0.0463 (13)0.0609 (15)0.0348 (12)0.0205 (12)0.0081 (10)0.0144 (11)
O11D0.0319 (8)0.0533 (9)0.0213 (7)0.0103 (7)0.0022 (6)0.0026 (6)
O12D0.0278 (7)0.0467 (9)0.0248 (7)0.0076 (7)0.0021 (6)0.0078 (6)
O21D0.0297 (7)0.0483 (9)0.0260 (7)0.0149 (7)0.0009 (6)0.0144 (6)
C1E0.0264 (10)0.0259 (10)0.0284 (10)0.0087 (8)0.0042 (8)0.0036 (8)
C2E0.0304 (10)0.0291 (11)0.0282 (10)0.0085 (9)0.0034 (8)0.0046 (8)
C3E0.0437 (12)0.0416 (13)0.0322 (11)0.0166 (11)0.0043 (9)0.0121 (9)
C4E0.0386 (12)0.0435 (13)0.0452 (13)0.0205 (11)0.0062 (10)0.0112 (10)
C5E0.0332 (11)0.0437 (13)0.0439 (13)0.0207 (10)0.0025 (9)0.0082 (10)
C6E0.0356 (11)0.0401 (12)0.0299 (11)0.0171 (10)0.0009 (9)0.0075 (9)
C11E0.0251 (9)0.0327 (11)0.0225 (10)0.0096 (9)0.0019 (8)0.0058 (8)
C12E0.0262 (10)0.0376 (12)0.0219 (9)0.0155 (9)0.0004 (8)0.0053 (8)
C13E0.0347 (11)0.0280 (11)0.0225 (10)0.0165 (9)0.0002 (8)0.0033 (8)
C21E0.0428 (12)0.0434 (13)0.0232 (10)0.0126 (10)0.0004 (9)0.0083 (9)
C22E0.0464 (13)0.0532 (15)0.0315 (12)0.0156 (11)0.0036 (10)0.0052 (10)
O11E0.0380 (8)0.0486 (9)0.0195 (7)0.0172 (7)0.0017 (6)0.0030 (6)
O12E0.0308 (7)0.0374 (8)0.0266 (7)0.0085 (6)0.0019 (6)0.0078 (6)
O21E0.0335 (7)0.0474 (9)0.0238 (7)0.0155 (7)0.0007 (6)0.0106 (6)
Geometric parameters (Å, º) top
C1C—C6C1.398 (2)C11D—H11D1.0000
C1C—C2C1.402 (2)C12D—C13D1.499 (2)
C1C—C11C1.463 (2)C12D—C11E1.593 (2)
C2C—O21C1.367 (2)C12D—H12D1.0000
C2C—C3C1.396 (2)C13D—O12D1.220 (2)
C3C—C4C1.382 (2)C13D—O11D1.323 (2)
C3C—H3C0.9500C21D—O21D1.431 (2)
C4C—C5C1.381 (3)C21D—C22D1.499 (3)
C4C—H4C0.9500C21D—H21G0.9900
C5C—C6C1.378 (3)C21D—H21H0.9900
C5C—H5C0.9500C22D—H22J0.9800
C6C—H6C0.9500C22D—H22K0.9800
C11C—C12C1.332 (2)C22D—H22L0.9800
C11C—H11C0.9500O11D—H1D0.93 (2)
C12C—C13C1.459 (3)C1E—C6E1.381 (2)
C12C—H12C0.9500C1E—C2E1.402 (2)
C13C—O12C1.227 (2)C1E—C11E1.514 (2)
C13C—O11C1.319 (2)C2E—O21E1.373 (2)
C21C—O21C1.435 (2)C2E—C3E1.391 (3)
C21C—C22C1.500 (2)C3E—C4E1.381 (3)
C21C—H21E0.9900C3E—H3E0.9500
C21C—H21F0.9900C4E—C5E1.375 (3)
C22C—H22G0.9800C4E—H4E0.9500
C22C—H22H0.9800C5E—C6E1.394 (3)
C22C—H22I0.9800C5E—H5E0.9500
O11C—H1C0.87 (2)C6E—H6E0.9500
C1D—C6D1.382 (2)C11E—C12E1.536 (2)
C1D—C2D1.403 (2)C11E—H11E1.0000
C1D—C11D1.507 (2)C12E—C13E1.498 (2)
C2D—O21D1.373 (2)C12E—H12E1.0000
C2D—C3D1.396 (2)C13E—O12E1.225 (2)
C3D—C4D1.381 (3)C13E—O11E1.315 (2)
C3D—H3D0.9500C21E—O21E1.436 (2)
C4D—C5D1.380 (3)C21E—C22E1.495 (3)
C4D—H4D0.9500C21E—H21I0.9900
C5D—C6D1.388 (3)C21E—H21J0.9900
C5D—H5D0.9500C22E—H22M0.9800
C6D—H6D0.9500C22E—H22N0.9800
C11D—C12D1.550 (2)C22E—H22O0.9800
C11D—C12E1.594 (2)O11E—H1E1.00 (3)
C6C—C1C—C2C117.67 (16)C13D—C12D—H12D112.8
C6C—C1C—C11C121.85 (16)C11D—C12D—H12D112.8
C2C—C1C—C11C120.39 (16)C11E—C12D—H12D112.8
O21C—C2C—C3C123.24 (16)O12D—C13D—O11D123.02 (16)
O21C—C2C—C1C116.35 (15)O12D—C13D—C12D123.59 (16)
C3C—C2C—C1C120.41 (17)O11D—C13D—C12D113.28 (16)
C4C—C3C—C2C119.66 (18)O21D—C21D—C22D107.72 (15)
C4C—C3C—H3C120.2O21D—C21D—H21G110.2
C2C—C3C—H3C120.2C22D—C21D—H21G110.2
C5C—C4C—C3C120.97 (18)O21D—C21D—H21H110.2
C5C—C4C—H4C119.5C22D—C21D—H21H110.2
C3C—C4C—H4C119.5H21G—C21D—H21H108.5
C6C—C5C—C4C118.95 (18)C21D—C22D—H22J109.5
C6C—C5C—H5C120.5C21D—C22D—H22K109.5
C4C—C5C—H5C120.5H22J—C22D—H22K109.5
C5C—C6C—C1C122.15 (18)C21D—C22D—H22L109.5
C5C—C6C—H6C118.9H22J—C22D—H22L109.5
C1C—C6C—H6C118.9H22K—C22D—H22L109.5
C12C—C11C—C1C126.20 (17)C13D—O11D—H1D108.9 (14)
C12C—C11C—H11C116.9C2D—O21D—C21D117.94 (14)
C1C—C11C—H11C116.9C6E—C1E—C2E118.45 (16)
C11C—C12C—C13C122.01 (18)C6E—C1E—C11E123.96 (16)
C11C—C12C—H12C119.0C2E—C1E—C11E117.23 (16)
C13C—C12C—H12C119.0O21E—C2E—C3E124.00 (17)
O12C—C13C—O11C122.82 (18)O21E—C2E—C1E115.58 (16)
O12C—C13C—C12C124.26 (18)C3E—C2E—C1E120.41 (18)
O11C—C13C—C12C112.92 (18)C4E—C3E—C2E119.65 (18)
O21C—C21C—C22C107.66 (14)C4E—C3E—H3E120.2
O21C—C21C—H21E110.2C2E—C3E—H3E120.2
C22C—C21C—H21E110.2C5E—C4E—C3E120.90 (18)
O21C—C21C—H21F110.2C5E—C4E—H4E119.5
C22C—C21C—H21F110.2C3E—C4E—H4E119.5
H21E—C21C—H21F108.5C4E—C5E—C6E119.19 (19)
C21C—C22C—H22G109.5C4E—C5E—H5E120.4
C21C—C22C—H22H109.5C6E—C5E—H5E120.4
H22G—C22C—H22H109.5C1E—C6E—C5E121.36 (18)
C21C—C22C—H22I109.5C1E—C6E—H6E119.3
H22G—C22C—H22I109.5C5E—C6E—H6E119.3
H22H—C22C—H22I109.5C1E—C11E—C12E119.79 (15)
C13C—O11C—H1C111.0 (16)C1E—C11E—C12D115.27 (14)
C2C—O21C—C21C117.72 (13)C12E—C11E—C12D90.64 (13)
C6D—C1D—C2D117.84 (17)C1E—C11E—H11E109.9
C6D—C1D—C11D124.08 (17)C12E—C11E—H11E109.9
C2D—C1D—C11D117.92 (16)C12D—C11E—H11E109.9
O21D—C2D—C3D123.45 (17)C13E—C12E—C11E115.75 (15)
O21D—C2D—C1D115.60 (16)C13E—C12E—C11D110.71 (14)
C3D—C2D—C1D120.95 (18)C11E—C12E—C11D89.85 (13)
C4D—C3D—C2D119.15 (18)C13E—C12E—H12E112.8
C4D—C3D—H3D120.4C11E—C12E—H12E112.8
C2D—C3D—H3D120.4C11D—C12E—H12E112.8
C5D—C4D—C3D121.02 (19)O12E—C13E—O11E123.30 (17)
C5D—C4D—H4D119.5O12E—C13E—C12E122.65 (16)
C3D—C4D—H4D119.5O11E—C13E—C12E113.87 (16)
C4D—C5D—C6D119.09 (19)O21E—C21E—C22E107.91 (15)
C4D—C5D—H5D120.5O21E—C21E—H21I110.1
C6D—C5D—H5D120.5C22E—C21E—H21I110.1
C1D—C6D—C5D121.93 (19)O21E—C21E—H21J110.1
C1D—C6D—H6D119.0C22E—C21E—H21J110.1
C5D—C6D—H6D119.0H21I—C21E—H21J108.4
C1D—C11D—C12D119.35 (15)C21E—C22E—H22M109.5
C1D—C11D—C12E115.79 (14)C21E—C22E—H22N109.5
C12D—C11D—C12E90.11 (13)H22M—C22E—H22N109.5
C1D—C11D—H11D110.0C21E—C22E—H22O109.5
C12D—C11D—H11D110.0H22M—C22E—H22O109.5
C12E—C11D—H11D110.0H22N—C22E—H22O109.5
C13D—C12D—C11D115.32 (14)C13E—O11E—H1E111.3 (13)
C13D—C12D—C11E111.78 (14)C2E—O21E—C21E117.75 (14)
C11D—C12D—C11E89.39 (12)
C6C—C1C—C2C—O21C175.72 (16)C11D—C12D—C13D—O11D157.79 (15)
C11C—C1C—C2C—O21C7.5 (3)C11E—C12D—C13D—O11D102.06 (18)
C6C—C1C—C2C—C3C4.8 (3)C3D—C2D—O21D—C21D13.5 (3)
C11C—C1C—C2C—C3C171.93 (18)C1D—C2D—O21D—C21D166.41 (16)
O21C—C2C—C3C—C4C177.16 (17)C22D—C21D—O21D—C2D173.53 (16)
C1C—C2C—C3C—C4C3.4 (3)C6E—C1E—C2E—O21E179.06 (16)
C2C—C3C—C4C—C5C0.6 (3)C11E—C1E—C2E—O21E7.5 (2)
C3C—C4C—C5C—C6C3.0 (3)C6E—C1E—C2E—C3E1.9 (3)
C4C—C5C—C6C—C1C1.5 (3)C11E—C1E—C2E—C3E171.59 (17)
C2C—C1C—C6C—C5C2.4 (3)O21E—C2E—C3E—C4E179.81 (17)
C11C—C1C—C6C—C5C174.30 (19)C1E—C2E—C3E—C4E0.8 (3)
C6C—C1C—C11C—C12C1.8 (3)C2E—C3E—C4E—C5E0.6 (3)
C2C—C1C—C11C—C12C174.82 (19)C3E—C4E—C5E—C6E0.9 (3)
C1C—C11C—C12C—C13C173.18 (18)C2E—C1E—C6E—C5E1.5 (3)
C11C—C12C—C13C—O12C8.8 (3)C11E—C1E—C6E—C5E171.44 (18)
C11C—C12C—C13C—O11C170.66 (18)C4E—C5E—C6E—C1E0.2 (3)
C3C—C2C—O21C—C21C6.5 (3)C6E—C1E—C11E—C12E7.0 (3)
C1C—C2C—O21C—C21C174.05 (16)C2E—C1E—C11E—C12E179.91 (16)
C22C—C21C—O21C—C2C173.43 (16)C6E—C1E—C11E—C12D99.5 (2)
C6D—C1D—C2D—O21D179.27 (16)C2E—C1E—C11E—C12D73.6 (2)
C11D—C1D—C2D—O21D3.6 (2)C13D—C12D—C11E—C1E7.5 (2)
C6D—C1D—C2D—C3D0.7 (3)C11D—C12D—C11E—C1E124.64 (15)
C11D—C1D—C2D—C3D176.28 (17)C13D—C12D—C11E—C12E116.19 (15)
O21D—C2D—C3D—C4D178.63 (17)C11D—C12D—C11E—C12E0.95 (13)
C1D—C2D—C3D—C4D1.3 (3)C1E—C11E—C12E—C13E126.16 (18)
C2D—C3D—C4D—C5D1.1 (3)C12D—C11E—C12E—C13E113.96 (16)
C3D—C4D—C5D—C6D0.4 (3)C1E—C11E—C12E—C11D120.81 (16)
C2D—C1D—C6D—C5D0.1 (3)C12D—C11E—C12E—C11D0.92 (12)
C11D—C1D—C6D—C5D175.20 (18)C1D—C11D—C12E—C13E4.5 (2)
C4D—C5D—C6D—C1D0.3 (3)C12D—C11D—C12E—C13E118.56 (15)
C6D—C1D—C11D—C12D13.3 (3)C1D—C11D—C12E—C11E122.10 (16)
C2D—C1D—C11D—C12D171.41 (15)C12D—C11D—C12E—C11E0.95 (13)
C6D—C1D—C11D—C12E92.7 (2)C11E—C12E—C13E—O12E19.5 (3)
C2D—C1D—C11D—C12E82.7 (2)C11D—C12E—C13E—O12E80.8 (2)
C1D—C11D—C12D—C13D126.99 (18)C11E—C12E—C13E—O11E165.26 (15)
C12E—C11D—C12D—C13D113.00 (16)C11D—C12E—C13E—O11E94.42 (18)
C1D—C11D—C12D—C11E119.10 (16)C3E—C2E—O21E—C21E18.3 (3)
C12E—C11D—C12D—C11E0.92 (12)C1E—C2E—O21E—C21E160.70 (16)
C11D—C12D—C13D—O12D25.9 (3)C22E—C21E—O21E—C2E168.97 (16)
C11E—C12D—C13D—O12D74.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11D—H1D···O12Di0.93 (2)1.80 (2)2.7139 (18)169 (2)
O11C—H1C···O12Eii0.87 (2)1.79 (2)2.6616 (18)177 (2)
O11E—H1E···O12Cii1.00 (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 formula0.124(C22H24O6)·2.752(C11H12O3)0.219(C22H24O6)·2.562(C11H12O3)0.680(C22H24O6)·1.640(C11H12O3)0.912(C22H24O6)·1.176(C11H12O3)
Mr576.62576.62576.62576.62
Crystal system, space groupTriclinic, P1Triclinic, P1Triclinic, P1Triclinic, P1
Temperature (K)173173173173
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)
V3)1492.4 (4)1490.4 (3)1480.8 (4)1471.6 (4)
Z2222
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.090.090.090.09
Crystal size (mm)0.38 × 0.33 × 0.240.45 × 0.24 × 0.140.45 × 0.24 × 0.140.45 × 0.24 × 0.14
Data collection
DiffractometerCCD 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
Rint0.0220.0230.0300.028
(sin θ/λ)max1)0.6060.6060.6060.606
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 reflections5500549954715439
No. of parameters390418409395
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.14, 0.210.16, 0.220.19, 0.350.19, 0.26


(rd48hlts)
Crystal data
Chemical formulaC22H24O6·C11H12O3
Mr576.62
Crystal system, space groupTriclinic, 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)
V3)1468.1 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.45 × 0.24 × 0.14
Data collection
DiffractometerCCD area detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
8381, 5409, 3394
Rint0.028
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.116, 1.01
No. of reflections5409
No. of parameters397
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.22

Computer programs: Bruker SMART, Bruker SHELXTL, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997).

Hydrogen-bond geometry (Å, º) for (d6hlt_s) top
D—H···AD—HH···AD···AD—H···A
O12A—H1A···O11Ai0.841.732.566 (3)170.4
O11B—H1B···O12Cii0.841.762.591 (2)167.7
O11C—H1C···O12Bii0.841.802.622 (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···AD—HH···AD···AD—H···A
O11A—H1A···O12Ai0.841.702.522 (5)166.4
O11B—H1B···O12Cii0.841.762.590 (3)169.8
O11C—H1C···O12Bii0.841.782.607 (4)168.2
O11E—H1E···O12Cii0.842.092.823 (6)145.9
O11C—H1C···O12Eii0.841.922.75 (2)168.9
O11D—H1D···O12Di0.842.333.094 (11)152.3
O11D—H1D···O12Ai0.842.182.929 (6)148.2
O11A—H1A···O12Di0.841.842.671 (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···AD—HH···AD···AD—H···A
O11A—H1A···O12Ai0.841.632.429 (8)157.6
O11B—H1B···O12Cii0.841.702.522 (5)167.0
O11C—H1C···O12Bii0.841.772.603 (5)170.6
O11E—H1E···O12Cii0.841.872.686 (3)163.7
O11C—H1C···O12Eii0.841.852.685 (4)171.0
O11D—H1D···O12Di0.842.052.798 (5)148.4
O11D—H1D···O12Ai0.842.022.727 (5)141.2
O11A—H1A···O12Di0.841.632.453 (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···AD—HH···AD···AD—H···A
O11A—H1A···O12Di0.841.662.472 (11)162.6
O11D—H1D···O12Ai0.842.022.702 (11)138.0
O11D—H1D···O12Di0.841.982.718 (3)145.6
O11C—H1C···O12Eii0.841.842.672 (2)172.0
O11E—H1E···O12Cii0.841.832.648 (2)163.0
O11C—H1C···O12Bii0.841.752.584 (12)171.9
O11B—H1B···O12Cii0.841.692.515 (12)166.8
O11A—H1A···O12Ai0.841.722.51 (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···AD—HH···AD···AD—H···A
O11D—H1D···O12Di0.93 (2)1.80 (2)2.7139 (18)169 (2)
O11C—H1C···O12Eii0.87 (2)1.79 (2)2.6616 (18)177 (2)
O11E—H1E···O12Cii1.00 (3)1.65 (3)2.6350 (18)169 (2)
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1, z+1.
 

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