In the title compound, C17H10F6O4S2·0.25C3H6O, there are two non-solvent molecules in the asymmetric unit, with different conformations. One is a photo-active antiparallel conformation in which the reactive C atoms are separated by 3.569 (6) Å. The other is a photo-inactive parallel conformation in which the reactive C atoms are separated by 4.541 (7) Å.
Supporting information
CCDC reference: 613579
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- Disorder in solvent or counterion
- R factor = 0.060
- wR factor = 0.149
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.25 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C36
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact F6 .. O1 .. 2.87 Ang.
Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _reflns_number_total 6969
From the CIF: _diffrn_reflns_limit_ max hkl 10. 16. 19.
From the CIF: _diffrn_reflns_limit_ min hkl 0. -16. -19.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 10. 18. 19.
Calculated minimum hkl -10. -18. -19.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
13 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
5,5'-Dimethyl-4,4'-(3,3,4,4,5,5-hexafluorocyclopentene-1,2-diyl)bis(thiophene-
2-carboxylic acid) acetone 0.25-solvate
top
Crystal data top
C17H10F6O4S2·0.25C3H6O | Z = 4 |
Mr = 470.89 | F(000) = 952 |
Triclinic, P1 | Dx = 1.530 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8885 (11) Å | Cell parameters from 59 reflections |
b = 15.1907 (17) Å | θ = 2.6–12.6° |
c = 16.734 (2) Å | µ = 0.34 mm−1 |
α = 68.855 (8)° | T = 295 K |
β = 84.902 (9)° | Prism, colorless |
γ = 75.965 (10)° | 0.5 × 0.3 × 0.2 mm |
V = 2044.5 (4) Å3 | |
Data collection top
Bruker P4 diffractometer | Rint = 0.026 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.3° |
Graphite monochromator | h = 0→10 |
ω scans | k = −16→16 |
7484 measured reflections | l = −19→19 |
6969 independent reflections | 3 standard reflections every 97 reflections |
3915 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.001P)2 + 4.P] where P = (Fo2 + 2Fc2)/3 |
6969 reflections | (Δ/σ)max = 0.003 |
570 parameters | Δρmax = 0.62 e Å−3 |
10 restraints | Δρmin = −0.33 e Å−3 |
Special details top
Experimental. IR (KBr, ν, cm-1): 742.6, 982.1, 1048.7, 1155.5, 1271.5, 1337.4, 1437.7,
156.1, 1700.6, 2854.4, 2913.8, 330.4. 1H NMR (CDCl3): δ 2.10 (s, 6H),
4.72 (s, 2H), 10.8 (s, 2H). MS m/z (M-): 454. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | 1.19205 (10) | 0.74957 (5) | 0.39120 (5) | 0.0703 (3) | |
S2 | 1.02762 (10) | 1.08593 (6) | 0.07307 (6) | 0.0792 (3) | |
S3 | 0.09609 (10) | 0.39194 (5) | 0.45779 (6) | 0.0747 (3) | |
S4 | 0.64401 (10) | 0.35530 (6) | 0.18364 (6) | 0.0832 (3) | |
O1 | 1.4763 (2) | 0.59428 (14) | 0.41921 (13) | 0.0738 (7) | |
O2 | 1.4186 (3) | 0.52955 (14) | 0.32863 (15) | 0.0916 (8) | |
H2A | 1.4994 | 0.4898 | 0.3474 | 0.137* | |
O3 | 0.8548 (3) | 1.28242 (16) | −0.01475 (18) | 0.1050 (10) | |
O4 | 0.6164 (3) | 1.25527 (16) | 0.01466 (16) | 0.0942 (9) | |
H4A | 0.5914 | 1.3140 | −0.0104 | 0.141* | |
O5 | −0.3017 (2) | 0.41552 (15) | 0.35934 (15) | 0.0886 (7) | |
O6 | −0.2366 (2) | 0.49106 (13) | 0.43895 (13) | 0.0739 (7) | |
H6A | −0.3292 | 0.5175 | 0.4336 | 0.111* | |
O7 | 0.4917 (3) | 0.55907 (17) | 0.08137 (18) | 0.1065 (10) | |
O8 | 0.2510 (3) | 0.54494 (17) | 0.12385 (19) | 0.1130 (11) | |
H8B | 0.2277 | 0.5943 | 0.0816 | 0.169* | |
F1 | 0.5366 (2) | 0.91163 (14) | 0.16565 (15) | 0.1070 (8) | |
F2 | 0.6447 (2) | 0.90601 (16) | 0.04732 (13) | 0.1080 (8) | |
F3 | 0.5217 (2) | 0.73916 (17) | 0.1815 (2) | 0.1534 (13) | |
F4 | 0.7144 (4) | 0.72465 (18) | 0.09837 (18) | 0.1558 (11) | |
F5 | 0.8544 (3) | 0.62425 (14) | 0.2378 (2) | 0.1508 (11) | |
F6 | 0.6955 (3) | 0.69443 (18) | 0.31087 (17) | 0.1417 (10) | |
F7 | 0.4814 (3) | 0.06947 (15) | 0.23910 (16) | 0.1611 (10) | |
F8 | 0.5587 (3) | 0.01724 (15) | 0.3701 (2) | 0.1431 (12) | |
F9 | 0.2122 (3) | 0.03388 (17) | 0.28494 (16) | 0.1397 (9) | |
F10 | 0.3433 (3) | −0.07071 (14) | 0.39361 (19) | 0.1480 (12) | |
F11 | 0.0562 (2) | 0.08947 (13) | 0.39895 (16) | 0.1128 (8) | |
F12 | 0.2453 (3) | 0.03370 (14) | 0.48653 (14) | 0.1130 (9) | |
C1 | 0.8711 (3) | 0.78212 (19) | 0.22515 (19) | 0.0623 (9) | |
C2 | 0.8097 (3) | 0.86889 (19) | 0.16554 (18) | 0.0607 (9) | |
C3 | 0.6602 (3) | 0.8647 (2) | 0.1324 (2) | 0.0727 (10) | |
C4 | 0.6582 (4) | 0.7583 (3) | 0.1644 (3) | 0.0949 (13) | |
C5 | 0.7756 (4) | 0.7103 (2) | 0.2345 (3) | 0.0874 (13) | |
C6 | 1.0214 (3) | 0.80153 (19) | 0.33484 (19) | 0.0637 (9) | |
C7 | 1.0045 (3) | 0.75323 (19) | 0.28233 (19) | 0.0617 (9) | |
C8 | 1.1303 (3) | 0.67189 (19) | 0.29009 (19) | 0.0654 (9) | |
H8A | 1.1363 | 0.6301 | 0.2602 | 0.078* | |
C9 | 1.2394 (3) | 0.66215 (19) | 0.34549 (19) | 0.0627 (9) | |
C10 | 0.9148 (4) | 0.8876 (2) | 0.3479 (2) | 0.0881 (12) | |
H10A | 0.8093 | 0.8847 | 0.3433 | 0.132* | |
H10B | 0.9348 | 0.9457 | 0.3050 | 0.132* | |
H10C | 0.9315 | 0.8877 | 0.4037 | 0.132* | |
C11 | 1.3888 (3) | 0.59142 (19) | 0.36728 (19) | 0.0669 (9) | |
C12 | 1.0163 (3) | 0.9684 (2) | 0.12016 (18) | 0.0649 (9) | |
C13 | 0.8638 (3) | 0.9591 (2) | 0.13173 (18) | 0.0610 (9) | |
C14 | 0.7583 (3) | 1.0509 (2) | 0.09955 (19) | 0.0683 (10) | |
H14A | 0.6511 | 1.0589 | 0.1013 | 0.082* | |
C15 | 0.8311 (4) | 1.1258 (2) | 0.06589 (19) | 0.0708 (10) | |
C16 | 1.1650 (3) | 0.8920 (2) | 0.1386 (2) | 0.0781 (11) | |
H16A | 1.1491 | 0.8349 | 0.1316 | 0.117* | |
H16B | 1.1968 | 0.8764 | 0.1964 | 0.117* | |
H16C | 1.2440 | 0.9158 | 0.0996 | 0.117* | |
C17 | 0.7633 (4) | 1.2284 (2) | 0.0198 (2) | 0.0808 (11) | |
C18 | 0.2570 (3) | 0.17558 (19) | 0.36835 (19) | 0.0650 (9) | |
C19 | 0.3824 (3) | 0.17218 (19) | 0.3185 (2) | 0.0682 (9) | |
C20 | 0.4345 (4) | 0.0717 (2) | 0.3140 (3) | 0.0957 (13) | |
C21 | 0.3016 (5) | 0.0232 (2) | 0.3500 (3) | 0.0927 (13) | |
C22 | 0.2074 (4) | 0.0812 (2) | 0.4022 (2) | 0.0762 (11) | |
C23 | 0.2331 (3) | 0.3004 (2) | 0.4391 (2) | 0.0696 (10) | |
C24 | 0.1698 (3) | 0.25780 (19) | 0.39359 (18) | 0.0603 (9) | |
C25 | 0.0110 (3) | 0.29972 (19) | 0.37594 (19) | 0.0655 (9) | |
H25A | −0.0493 | 0.2790 | 0.3468 | 0.079* | |
C26 | −0.0448 (3) | 0.37337 (19) | 0.40580 (18) | 0.0617 (9) | |
C27 | 0.3965 (4) | 0.2755 (2) | 0.4704 (2) | 0.0943 (12) | |
H27A | 0.4356 | 0.2065 | 0.4890 | 0.141* | |
H27B | 0.3981 | 0.2972 | 0.5175 | 0.141* | |
H27C | 0.4603 | 0.3067 | 0.4248 | 0.141* | |
C28 | −0.2053 (3) | 0.4291 (2) | 0.40033 (19) | 0.0671 (10) | |
C29 | 0.6110 (4) | 0.2461 (2) | 0.2501 (2) | 0.0721 (10) | |
C30 | 0.4552 (3) | 0.2516 (2) | 0.2677 (2) | 0.0675 (9) | |
C31 | 0.3659 (4) | 0.3463 (2) | 0.2261 (2) | 0.0768 (11) | |
H31A | 0.2588 | 0.3636 | 0.2315 | 0.092* | |
C32 | 0.4514 (4) | 0.4095 (2) | 0.1777 (2) | 0.0772 (11) | |
C33 | 0.7488 (4) | 0.1630 (3) | 0.2816 (3) | 0.1027 (15) | |
H33A | 0.7488 | 0.1380 | 0.3431 | 0.154* | |
H33B | 0.8423 | 0.1851 | 0.2613 | 0.154* | |
H33C | 0.7434 | 0.1128 | 0.2606 | 0.154* | |
C34 | 0.3977 (4) | 0.5106 (2) | 0.1242 (2) | 0.0875 (12) | |
O9 | 0.0476 (6) | 0.2636 (4) | 0.1921 (3) | 0.1075 (18) | 0.50 |
C35 | 0.1823 (8) | 0.3143 (7) | 0.0649 (4) | 0.231 (3) | 0.50 |
H35A | 0.2464 | 0.3601 | 0.0532 | 0.346* | 0.50 |
H35B | 0.1308 | 0.3242 | 0.0132 | 0.346* | 0.50 |
H35C | 0.2456 | 0.2496 | 0.0855 | 0.346* | 0.50 |
C36 | 0.0668 (7) | 0.3278 (4) | 0.1297 (4) | 0.123 (3) | 0.50 |
C37 | −0.0119 (9) | 0.4300 (4) | 0.1064 (7) | 0.190 (4) | 0.50 |
H37A | 0.0195 | 0.4565 | 0.1446 | 0.284* | 0.50 |
H37B | −0.1221 | 0.4359 | 0.1105 | 0.284* | 0.50 |
H37C | 0.0150 | 0.4649 | 0.0487 | 0.284* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0704 (5) | 0.0604 (4) | 0.0701 (4) | −0.0007 (4) | −0.0038 (4) | −0.0196 (3) |
S2 | 0.0674 (4) | 0.0795 (5) | 0.0815 (5) | −0.0281 (4) | −0.0017 (4) | −0.0099 (4) |
S3 | 0.0659 (5) | 0.0645 (4) | 0.0981 (5) | −0.0066 (4) | −0.0047 (4) | −0.0381 (4) |
S4 | 0.0709 (5) | 0.0795 (5) | 0.0973 (6) | −0.0181 (4) | 0.0030 (4) | −0.0291 (4) |
O1 | 0.0609 (12) | 0.0739 (12) | 0.0792 (13) | −0.0026 (10) | −0.0072 (10) | −0.0248 (10) |
O2 | 0.0696 (13) | 0.0740 (12) | 0.1316 (17) | 0.0126 (11) | −0.0252 (12) | −0.0493 (11) |
O3 | 0.0883 (15) | 0.0751 (14) | 0.129 (2) | −0.0287 (12) | −0.0119 (15) | −0.0002 (14) |
O4 | 0.0838 (15) | 0.0666 (13) | 0.1139 (18) | −0.0124 (12) | −0.0052 (14) | −0.0120 (12) |
O5 | 0.0650 (13) | 0.0877 (12) | 0.1216 (15) | 0.0057 (11) | −0.0195 (12) | −0.0572 (11) |
O6 | 0.0643 (12) | 0.0663 (11) | 0.0883 (13) | 0.0037 (10) | −0.0032 (10) | −0.0350 (9) |
O7 | 0.0963 (16) | 0.0760 (14) | 0.129 (2) | −0.0242 (13) | 0.0165 (16) | −0.0150 (14) |
O8 | 0.0909 (17) | 0.0697 (14) | 0.142 (2) | −0.0113 (13) | −0.0051 (17) | 0.0024 (15) |
F1 | 0.0477 (9) | 0.1037 (12) | 0.1702 (18) | −0.0086 (9) | 0.0074 (11) | −0.0561 (12) |
F2 | 0.0935 (12) | 0.1312 (15) | 0.0944 (13) | −0.0418 (11) | −0.0242 (11) | −0.0176 (12) |
F3 | 0.0795 (12) | 0.1094 (15) | 0.236 (3) | −0.0440 (11) | −0.0282 (16) | 0.0014 (17) |
F4 | 0.187 (3) | 0.1324 (16) | 0.171 (2) | −0.0208 (18) | −0.0316 (19) | −0.0830 (14) |
F5 | 0.1073 (15) | 0.0698 (11) | 0.279 (3) | −0.0059 (11) | −0.0609 (17) | −0.0605 (14) |
F6 | 0.1337 (16) | 0.1452 (17) | 0.132 (2) | −0.0801 (14) | 0.0138 (15) | −0.0035 (15) |
F7 | 0.217 (2) | 0.1248 (12) | 0.1897 (16) | −0.0748 (14) | 0.1151 (16) | −0.1149 (11) |
F8 | 0.0901 (15) | 0.0753 (13) | 0.234 (3) | 0.0172 (12) | −0.0091 (17) | −0.0400 (15) |
F9 | 0.1478 (19) | 0.1645 (16) | 0.1513 (17) | −0.0615 (15) | 0.0048 (15) | −0.0919 (13) |
F10 | 0.152 (2) | 0.0527 (10) | 0.218 (3) | −0.0073 (13) | 0.0371 (19) | −0.0417 (13) |
F11 | 0.0765 (12) | 0.0754 (11) | 0.186 (2) | −0.0201 (10) | 0.0015 (13) | −0.0436 (12) |
F12 | 0.1468 (18) | 0.0752 (12) | 0.0994 (14) | −0.0223 (12) | 0.0042 (14) | −0.0127 (11) |
C1 | 0.0458 (14) | 0.0577 (14) | 0.0792 (18) | −0.0086 (12) | 0.0042 (13) | −0.0220 (13) |
C2 | 0.0475 (14) | 0.0632 (15) | 0.0683 (17) | −0.0118 (12) | 0.0051 (13) | −0.0212 (13) |
C3 | 0.0518 (16) | 0.0743 (18) | 0.082 (2) | −0.0113 (14) | −0.0053 (15) | −0.0157 (16) |
C4 | 0.070 (2) | 0.084 (2) | 0.129 (3) | −0.0228 (17) | −0.012 (2) | −0.029 (2) |
C5 | 0.0656 (19) | 0.0614 (18) | 0.123 (3) | −0.0085 (16) | −0.004 (2) | −0.0203 (18) |
C6 | 0.0582 (16) | 0.0526 (14) | 0.0693 (17) | −0.0039 (13) | 0.0060 (14) | −0.0156 (13) |
C7 | 0.0515 (15) | 0.0511 (14) | 0.0713 (17) | −0.0044 (12) | 0.0011 (14) | −0.0133 (13) |
C8 | 0.0638 (17) | 0.0502 (14) | 0.0784 (18) | −0.0071 (13) | −0.0005 (15) | −0.0218 (13) |
C9 | 0.0562 (16) | 0.0526 (14) | 0.0725 (17) | −0.0050 (13) | 0.0024 (14) | −0.0195 (13) |
C10 | 0.087 (2) | 0.0772 (19) | 0.089 (2) | 0.0148 (18) | −0.0046 (18) | −0.0359 (16) |
C11 | 0.0631 (17) | 0.0501 (14) | 0.0796 (19) | −0.0047 (13) | 0.0037 (15) | −0.0195 (14) |
C12 | 0.0555 (15) | 0.0724 (17) | 0.0583 (16) | −0.0160 (14) | −0.0011 (13) | −0.0119 (13) |
C13 | 0.0530 (15) | 0.0609 (15) | 0.0600 (16) | −0.0107 (13) | −0.0003 (13) | −0.0118 (13) |
C14 | 0.0552 (16) | 0.0712 (17) | 0.0711 (18) | −0.0128 (14) | 0.0023 (14) | −0.0178 (14) |
C15 | 0.0665 (17) | 0.0668 (17) | 0.0686 (18) | −0.0135 (15) | −0.0054 (15) | −0.0113 (14) |
C16 | 0.0518 (16) | 0.089 (2) | 0.077 (2) | −0.0146 (15) | 0.0057 (15) | −0.0122 (17) |
C17 | 0.082 (2) | 0.0722 (19) | 0.080 (2) | −0.0190 (17) | −0.0059 (18) | −0.0148 (16) |
C18 | 0.0580 (16) | 0.0524 (14) | 0.0779 (18) | −0.0015 (13) | −0.0051 (14) | −0.0208 (13) |
C19 | 0.0621 (17) | 0.0496 (14) | 0.0862 (19) | 0.0018 (13) | −0.0064 (15) | −0.0239 (13) |
C20 | 0.083 (2) | 0.0614 (17) | 0.138 (3) | 0.0000 (17) | 0.013 (2) | −0.0423 (18) |
C21 | 0.100 (3) | 0.0586 (17) | 0.120 (3) | −0.0125 (18) | −0.002 (2) | −0.0354 (17) |
C22 | 0.0636 (18) | 0.0595 (16) | 0.097 (2) | −0.0049 (15) | −0.0079 (17) | −0.0213 (16) |
C23 | 0.0586 (16) | 0.0578 (15) | 0.087 (2) | −0.0052 (14) | −0.0054 (15) | −0.0235 (14) |
C24 | 0.0574 (16) | 0.0508 (14) | 0.0680 (16) | −0.0059 (12) | −0.0012 (13) | −0.0192 (12) |
C25 | 0.0608 (16) | 0.0596 (15) | 0.0748 (17) | −0.0059 (13) | −0.0042 (14) | −0.0262 (13) |
C26 | 0.0531 (15) | 0.0555 (14) | 0.0695 (17) | −0.0047 (13) | −0.0014 (13) | −0.0185 (13) |
C27 | 0.0674 (19) | 0.093 (2) | 0.133 (3) | −0.0057 (17) | −0.0242 (19) | −0.0548 (18) |
C28 | 0.0639 (17) | 0.0543 (15) | 0.0725 (18) | −0.0034 (14) | −0.0005 (15) | −0.0162 (14) |
C29 | 0.0717 (19) | 0.0669 (16) | 0.0773 (18) | −0.0091 (15) | −0.0063 (15) | −0.0277 (14) |
C30 | 0.0619 (17) | 0.0560 (14) | 0.0821 (18) | −0.0054 (13) | 0.0035 (15) | −0.0270 (13) |
C31 | 0.0590 (17) | 0.0631 (17) | 0.097 (2) | −0.0048 (15) | 0.0018 (17) | −0.0210 (16) |
C32 | 0.075 (2) | 0.0633 (16) | 0.088 (2) | −0.0094 (15) | −0.0005 (17) | −0.0245 (15) |
C33 | 0.065 (2) | 0.089 (2) | 0.140 (3) | −0.0022 (19) | −0.018 (2) | −0.029 (2) |
C34 | 0.074 (2) | 0.0689 (19) | 0.109 (3) | −0.0091 (17) | −0.007 (2) | −0.0217 (18) |
O9 | 0.101 (3) | 0.151 (4) | 0.089 (3) | −0.060 (3) | 0.011 (3) | −0.046 (3) |
C35 | 0.237 (6) | 0.484 (8) | 0.137 (5) | −0.286 (5) | 0.100 (5) | −0.196 (5) |
C36 | 0.127 (4) | 0.177 (5) | 0.094 (5) | −0.109 (4) | −0.024 (4) | −0.029 (4) |
C37 | 0.147 (5) | 0.240 (7) | 0.208 (10) | −0.157 (4) | −0.033 (6) | −0.028 (7) |
Geometric parameters (Å, º) top
S1—C9 | 1.712 (3) | C10—H10B | 0.960 |
S1—C6 | 1.717 (3) | C10—H10C | 0.960 |
S2—C12 | 1.696 (3) | C12—C13 | 1.386 (4) |
S2—C15 | 1.704 (3) | C12—C16 | 1.503 (4) |
S3—C23 | 1.714 (3) | C13—C14 | 1.424 (4) |
S3—C26 | 1.717 (3) | C14—C15 | 1.364 (4) |
S4—C32 | 1.705 (3) | C14—H14A | 0.930 |
S4—C29 | 1.710 (3) | C15—C17 | 1.465 (4) |
O1—C11 | 1.235 (4) | C16—H16A | 0.960 |
O2—C11 | 1.288 (4) | C16—H16B | 0.960 |
O2—H2A | 0.820 | C16—H16C | 0.960 |
O3—C17 | 1.252 (4) | C18—C19 | 1.333 (4) |
O4—C17 | 1.271 (4) | C18—C24 | 1.481 (4) |
O4—H4A | 0.820 | C18—C22 | 1.499 (4) |
O5—C28 | 1.241 (4) | C19—C30 | 1.463 (4) |
O6—C28 | 1.288 (4) | C19—C20 | 1.512 (4) |
O6—H6A | 0.820 | C20—C21 | 1.509 (5) |
O7—C34 | 1.251 (4) | C21—C22 | 1.519 (5) |
O8—C34 | 1.281 (4) | C23—C24 | 1.387 (5) |
O8—H8B | 0.820 | C23—C27 | 1.501 (4) |
F1—C3 | 1.350 (4) | C24—C25 | 1.409 (4) |
F2—C3 | 1.337 (4) | C25—C26 | 1.355 (4) |
F3—C4 | 1.299 (4) | C25—H25A | 0.930 |
F4—C4 | 1.385 (5) | C26—C28 | 1.464 (4) |
F5—C5 | 1.309 (4) | C27—H27A | 0.960 |
F6—C5 | 1.378 (4) | C27—H27B | 0.960 |
F7—C20 | 1.294 (5) | C27—H27C | 0.960 |
F8—C20 | 1.402 (4) | C29—C30 | 1.378 (4) |
F9—C21 | 1.344 (5) | C29—C33 | 1.502 (4) |
F10—C21 | 1.321 (4) | C30—C31 | 1.417 (4) |
F11—C22 | 1.323 (4) | C31—C32 | 1.356 (4) |
F12—C22 | 1.363 (4) | C31—H31A | 0.930 |
C1—C2 | 1.353 (3) | C32—C34 | 1.454 (4) |
C1—C7 | 1.470 (4) | C33—H33A | 0.960 |
C1—C5 | 1.496 (5) | C33—H33B | 0.960 |
C2—C13 | 1.464 (4) | C33—H33C | 0.960 |
C2—C3 | 1.508 (4) | O9—C36 | 1.178 (6) |
C3—C4 | 1.512 (5) | C35—C36 | 1.461 (7) |
C4—C5 | 1.492 (5) | C35—H35A | 0.960 |
C6—C7 | 1.369 (5) | C35—H35B | 0.960 |
C6—C10 | 1.491 (4) | C35—H35C | 0.960 |
C7—C8 | 1.426 (4) | C36—C37 | 1.462 (7) |
C8—C9 | 1.347 (4) | C37—H37A | 0.960 |
C8—H8A | 0.930 | C37—H37B | 0.960 |
C9—C11 | 1.471 (4) | C37—H37C | 0.960 |
C10—H10A | 0.960 | | |
| | | |
C9—S1—C6 | 91.83 (15) | C18—C19—C20 | 109.1 (3) |
C12—S2—C15 | 92.59 (15) | C30—C19—C20 | 122.4 (3) |
C23—S3—C26 | 92.18 (16) | F7—C20—F8 | 106.2 (3) |
C32—S4—C29 | 92.39 (15) | F7—C20—C21 | 114.4 (4) |
C11—O2—H2A | 109.5 | F8—C20—C21 | 105.3 (3) |
C17—O4—H4A | 109.5 | F7—C20—C19 | 114.8 (3) |
C28—O6—H6A | 109.5 | F8—C20—C19 | 110.4 (3) |
C34—O8—H8B | 109.5 | C21—C20—C19 | 105.4 (3) |
C2—C1—C7 | 130.1 (3) | F10—C21—F9 | 106.9 (3) |
C2—C1—C5 | 110.9 (3) | F10—C21—C20 | 114.8 (3) |
C7—C1—C5 | 118.8 (2) | F9—C21—C20 | 108.8 (3) |
C1—C2—C13 | 131.2 (3) | F10—C21—C22 | 113.6 (3) |
C1—C2—C3 | 109.5 (3) | F9—C21—C22 | 107.7 (3) |
C13—C2—C3 | 119.3 (2) | C20—C21—C22 | 104.9 (3) |
F2—C3—F1 | 105.8 (2) | F11—C22—F12 | 105.0 (3) |
F2—C3—C2 | 113.8 (3) | F11—C22—C18 | 114.6 (2) |
F1—C3—C2 | 110.9 (3) | F12—C22—C18 | 110.9 (3) |
F2—C3—C4 | 112.6 (3) | F11—C22—C21 | 113.4 (3) |
F1—C3—C4 | 108.5 (3) | F12—C22—C21 | 109.0 (2) |
C2—C3—C4 | 105.2 (2) | C18—C22—C21 | 104.0 (3) |
F3—C4—F4 | 105.0 (4) | C24—C23—C27 | 128.3 (3) |
F3—C4—C5 | 116.8 (3) | C24—C23—S3 | 110.7 (2) |
F4—C4—C5 | 106.7 (3) | C27—C23—S3 | 121.0 (3) |
F3—C4—C3 | 115.3 (3) | C23—C24—C25 | 112.4 (3) |
F4—C4—C3 | 106.8 (3) | C23—C24—C18 | 124.1 (3) |
C5—C4—C3 | 105.6 (3) | C25—C24—C18 | 123.4 (3) |
F5—C5—F6 | 104.8 (3) | C26—C25—C24 | 113.2 (3) |
F5—C5—C4 | 114.3 (4) | C26—C25—H25A | 123.4 |
F6—C5—C4 | 107.1 (3) | C24—C25—H25A | 123.4 |
F5—C5—C1 | 115.2 (3) | C25—C26—C28 | 126.4 (3) |
F6—C5—C1 | 109.3 (3) | C25—C26—S3 | 111.5 (2) |
C4—C5—C1 | 105.9 (3) | C28—C26—S3 | 122.0 (2) |
C7—C6—C10 | 129.1 (3) | C23—C27—H27A | 109.5 |
C7—C6—S1 | 111.2 (2) | C23—C27—H27B | 109.5 |
C10—C6—S1 | 119.7 (3) | H27A—C27—H27B | 109.5 |
C6—C7—C8 | 112.2 (3) | C23—C27—H27C | 109.5 |
C6—C7—C1 | 123.5 (2) | H27A—C27—H27C | 109.5 |
C8—C7—C1 | 124.2 (3) | H27B—C27—H27C | 109.5 |
C9—C8—C7 | 112.7 (3) | O5—C28—O6 | 124.0 (3) |
C9—C8—H8A | 123.7 | O5—C28—C26 | 119.6 (3) |
C7—C8—H8A | 123.7 | O6—C28—C26 | 116.4 (3) |
C8—C9—C11 | 129.0 (3) | C30—C29—C33 | 130.7 (3) |
C8—C9—S1 | 112.1 (2) | C30—C29—S4 | 111.4 (2) |
C11—C9—S1 | 118.8 (2) | C33—C29—S4 | 117.9 (2) |
C6—C10—H10A | 109.5 | C29—C30—C31 | 111.4 (3) |
C6—C10—H10B | 109.5 | C29—C30—C19 | 127.0 (2) |
H10A—C10—H10B | 109.5 | C31—C30—C19 | 121.5 (3) |
C6—C10—H10C | 109.5 | C32—C31—C30 | 113.7 (3) |
H10A—C10—H10C | 109.5 | C32—C31—H31A | 123.2 |
H10B—C10—H10C | 109.5 | C30—C31—H31A | 123.2 |
O1—C11—O2 | 124.5 (3) | C31—C32—C34 | 128.3 (3) |
O1—C11—C9 | 120.1 (3) | C31—C32—S4 | 111.2 (2) |
O2—C11—C9 | 115.4 (3) | C34—C32—S4 | 120.5 (3) |
C13—C12—C16 | 130.1 (3) | C29—C33—H33A | 109.5 |
C13—C12—S2 | 111.7 (2) | C29—C33—H33B | 109.5 |
C16—C12—S2 | 118.1 (2) | H33A—C33—H33B | 109.5 |
C12—C13—C14 | 111.3 (3) | C29—C33—H33C | 109.5 |
C12—C13—C2 | 127.0 (2) | H33A—C33—H33C | 109.5 |
C14—C13—C2 | 121.5 (3) | H33B—C33—H33C | 109.5 |
C15—C14—C13 | 112.9 (3) | O7—C34—O8 | 123.4 (3) |
C15—C14—H14A | 123.6 | O7—C34—C32 | 120.7 (3) |
C13—C14—H14A | 123.6 | O8—C34—C32 | 116.0 (3) |
C14—C15—C17 | 128.7 (3) | C36—C35—H35A | 109.5 |
C14—C15—S2 | 111.5 (2) | C36—C35—H35B | 109.5 |
C17—C15—S2 | 119.5 (2) | H35A—C35—H35B | 109.5 |
C12—C16—H16A | 109.5 | C36—C35—H35C | 109.5 |
C12—C16—H16B | 109.5 | H35A—C35—H35C | 109.5 |
H16A—C16—H16B | 109.5 | H35B—C35—H35C | 109.5 |
C12—C16—H16C | 109.5 | O9—C36—C35 | 122.6 (6) |
H16A—C16—H16C | 109.5 | O9—C36—C37 | 127.1 (7) |
H16B—C16—H16C | 109.5 | C35—C36—C37 | 110.3 (6) |
O3—C17—O4 | 124.7 (3) | C36—C37—H37A | 109.5 |
O3—C17—C15 | 117.4 (3) | C36—C37—H37B | 109.5 |
O4—C17—C15 | 117.8 (3) | H37A—C37—H37B | 109.5 |
C19—C18—C24 | 128.1 (3) | C36—C37—H37C | 109.5 |
C19—C18—C22 | 112.4 (3) | H37A—C37—H37C | 109.5 |
C24—C18—C22 | 119.5 (3) | H37B—C37—H37C | 109.5 |
C18—C19—C30 | 128.3 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O5i | 0.82 | 1.84 | 2.635 (3) | 164 |
O4—H4A···O7ii | 0.82 | 1.87 | 2.674 (3) | 168 |
O6—H6A···O1iii | 0.82 | 1.82 | 2.630 (3) | 171 |
O8—H8B···O3ii | 0.82 | 1.81 | 2.598 (3) | 162 |
Symmetry codes: (i) x+2, y, z; (ii) −x+1, −y+2, −z; (iii) x−2, y, z. |