Crystals of the title calixarene containing CCl4 as solvent have already been investigated [Baudry, Felix, Bavoux, Perrin, Vocanson, Dumazet-Bonnamour & Lamartine (2003). New J. Chem. pp. 1540-1543]. We present here a new pseudopolymorph of this compound, C64H56Br8O8·2C4H8O, containing tetrahydrofuran as solvent and crystallizing in a different space group. However, the molecular conformation of both molecules is very similar. Further similarities of both structures are that the calixarene molecules are located on a centre of inversion and that the solvent molecules occupy similar positions with respect to the calixarene molecules.
Supporting information
CCDC reference: 226970
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.043
- wR factor = 0.111
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT410_ALERT_2_A Short Intra H...H Contact H53B .. H55B = 1.75 Ang.
| Author Response: This short distance arises from the fact that the
THF molecule is disordered and not well determined.
|
PLAT413_ALERT_2_A Short Inter XH3 .. XHn H17A .. H55A = 1.82 Ang.
| Author Response: This short distance arised most probably from the fact that
the THF molecule is disordered. The C atom C55 is not well determined
and as a result of that the position of the attached H atom are not
very reliable.
|
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.109
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.61 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.03 Ratio
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors .... O51
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors .... C54
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C52
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C53
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C55
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
PLAT731_ALERT_1_C Bond Calc 1.40(3), Rep 1.396(9) ...... 3.33 su-Rat
O51 -C52 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 1.36(3), Rep 1.359(10) ...... 3.00 su-Rat
O51 -C55 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 1.53(3), Rep 1.529(9) ...... 3.33 su-Rat
C52 -C53 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 1.54(4), Rep 1.532(10) ...... 4.00 su-Rat
C53 -C54 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 1.51(3), Rep 1.513(10) ...... 3.00 su-Rat
C54 -C55 1.555 1.555
2 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
16 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON.
Crystal data top
C64H56Br8O8·2C4H8O | F(000) = 1728 |
Mr = 1736.58 | Dx = 1.603 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 30238 reflections |
a = 9.0636 (7) Å | θ = 1.9–25.3° |
b = 26.2897 (15) Å | µ = 4.52 mm−1 |
c = 15.1205 (11) Å | T = 293 K |
β = 93.287 (6)° | Block, colourless |
V = 3597.0 (4) Å3 | 0.57 × 0.54 × 0.52 mm |
Z = 2 | |
Data collection top
Stoe IPDS-II two-circle diffractometer | 6572 independent reflections |
Radiation source: fine-focus sealed tube | 4601 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.109 |
ω scans | θmax = 25.4°, θmin = 2.1° |
Absorption correction: empirical (using intensity measurements) (MULABS; Spek, 1990; Blessing, 1995) | h = −10→10 |
Tmin = 0.086, Tmax = 0.094 | k = −31→31 |
56958 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0614P)2] where P = (Fo2 + 2Fc2)/3 |
6572 reflections | (Δ/σ)max < 0.001 |
406 parameters | Δρmax = 0.47 e Å−3 |
5 restraints | Δρmin = −0.60 e Å−3 |
Special details top
Experimental. ; |
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 | |
C1 | 0.7061 (5) | 0.39442 (18) | 0.7944 (3) | 0.0617 (12) | |
H1A | 0.7994 | 0.4061 | 0.7735 | 0.074* | |
H1B | 0.7278 | 0.3763 | 0.8495 | 0.074* | |
C11 | 0.6391 (5) | 0.35718 (16) | 0.7274 (3) | 0.0528 (10) | |
C12 | 0.6956 (5) | 0.35159 (15) | 0.6439 (3) | 0.0510 (10) | |
O12 | 0.8109 (4) | 0.38164 (13) | 0.6200 (2) | 0.0703 (9) | |
C17 | 0.7702 (10) | 0.4309 (2) | 0.5917 (5) | 0.117 (3) | |
H17A | 0.8566 | 0.4492 | 0.5761 | 0.176* | |
H17B | 0.7245 | 0.4484 | 0.6386 | 0.176* | |
H17C | 0.7018 | 0.4286 | 0.5409 | 0.176* | |
C13 | 0.6466 (5) | 0.31330 (15) | 0.5857 (2) | 0.0458 (9) | |
C14 | 0.5363 (5) | 0.28114 (16) | 0.6105 (2) | 0.0483 (9) | |
H14 | 0.5005 | 0.2558 | 0.5720 | 0.058* | |
C15 | 0.4792 (5) | 0.28662 (16) | 0.6927 (3) | 0.0513 (9) | |
Br15 | 0.33351 (6) | 0.24018 (2) | 0.72801 (4) | 0.07697 (17) | |
C16 | 0.5293 (5) | 0.32390 (17) | 0.7507 (3) | 0.0533 (10) | |
H16 | 0.4894 | 0.3268 | 0.8058 | 0.064* | |
C2 | 0.7219 (5) | 0.30652 (18) | 0.4988 (3) | 0.0557 (10) | |
H2A | 0.7380 | 0.3398 | 0.4734 | 0.067* | |
H2B | 0.8179 | 0.2910 | 0.5114 | 0.067* | |
C21 | 0.6362 (4) | 0.27447 (15) | 0.4313 (2) | 0.0451 (9) | |
C22 | 0.5280 (5) | 0.29586 (15) | 0.3734 (3) | 0.0485 (9) | |
O22 | 0.4970 (4) | 0.34690 (11) | 0.3803 (2) | 0.0691 (9) | |
C27 | 0.5832 (8) | 0.3799 (2) | 0.3273 (4) | 0.0911 (19) | |
H27A | 0.5547 | 0.4146 | 0.3365 | 0.137* | |
H27B | 0.5661 | 0.3714 | 0.2658 | 0.137* | |
H27C | 0.6862 | 0.3758 | 0.3443 | 0.137* | |
C23 | 0.4441 (4) | 0.26634 (15) | 0.3127 (2) | 0.0458 (9) | |
C24 | 0.4747 (5) | 0.21487 (15) | 0.3089 (3) | 0.0482 (9) | |
H24 | 0.4208 | 0.1944 | 0.2687 | 0.058* | |
C25 | 0.5842 (5) | 0.19366 (15) | 0.3644 (3) | 0.0469 (9) | |
Br25 | 0.62898 (6) | 0.123627 (18) | 0.35221 (4) | 0.07238 (16) | |
C26 | 0.6627 (5) | 0.22280 (16) | 0.4263 (2) | 0.0484 (9) | |
H26 | 0.7336 | 0.2077 | 0.4647 | 0.058* | |
C3 | 0.3228 (5) | 0.28940 (17) | 0.2527 (3) | 0.0550 (10) | |
H3A | 0.2518 | 0.2630 | 0.2358 | 0.066* | |
H3B | 0.2718 | 0.3150 | 0.2857 | 0.066* | |
C31 | 0.3765 (4) | 0.31349 (15) | 0.1700 (2) | 0.0458 (9) | |
C32 | 0.3263 (4) | 0.36134 (15) | 0.1413 (3) | 0.0474 (9) | |
O32 | 0.2281 (4) | 0.38757 (12) | 0.1904 (2) | 0.0620 (8) | |
C37 | 0.0771 (7) | 0.3752 (3) | 0.1706 (5) | 0.103 (2) | |
H37A | 0.0161 | 0.3950 | 0.2074 | 0.155* | |
H37B | 0.0618 | 0.3397 | 0.1816 | 0.155* | |
H37C | 0.0516 | 0.3825 | 0.1094 | 0.155* | |
C33 | 0.3806 (5) | 0.38552 (14) | 0.0674 (2) | 0.0465 (9) | |
C34 | 0.4831 (5) | 0.36075 (16) | 0.0203 (2) | 0.0500 (9) | |
H34 | 0.5203 | 0.3762 | −0.0291 | 0.060* | |
C35 | 0.5321 (5) | 0.31235 (17) | 0.0461 (3) | 0.0543 (10) | |
Br35 | 0.67402 (8) | 0.27925 (3) | −0.02113 (3) | 0.0924 (2) | |
C36 | 0.4797 (5) | 0.28928 (15) | 0.1197 (3) | 0.0517 (10) | |
H36 | 0.5137 | 0.2571 | 0.1361 | 0.062* | |
C4 | 0.3323 (5) | 0.43910 (14) | 0.0443 (3) | 0.0517 (10) | |
H4A | 0.2255 | 0.4412 | 0.0454 | 0.062* | |
H4B | 0.3589 | 0.4468 | −0.0155 | 0.062* | |
C41 | 0.4014 (5) | 0.47832 (14) | 0.1072 (2) | 0.0461 (9) | |
C42 | 0.3240 (5) | 0.52200 (15) | 0.1295 (2) | 0.0474 (9) | |
O42 | 0.1783 (3) | 0.52798 (11) | 0.09890 (19) | 0.0551 (7) | |
C47 | 0.1557 (6) | 0.5500 (2) | 0.0138 (3) | 0.0723 (13) | |
H47A | 0.0517 | 0.5527 | −0.0012 | 0.108* | |
H47B | 0.2008 | 0.5289 | −0.0290 | 0.108* | |
H47C | 0.1995 | 0.5832 | 0.0139 | 0.108* | |
C43 | 0.3866 (5) | 0.55924 (16) | 0.1859 (3) | 0.0495 (9) | |
C44 | 0.5290 (5) | 0.55173 (16) | 0.2215 (3) | 0.0546 (10) | |
H44 | 0.5730 | 0.5757 | 0.2598 | 0.065* | |
C45 | 0.6058 (5) | 0.50834 (16) | 0.1999 (3) | 0.0535 (10) | |
Br45 | 0.80141 (6) | 0.49795 (2) | 0.24765 (4) | 0.07917 (18) | |
C46 | 0.5436 (5) | 0.47218 (15) | 0.1435 (3) | 0.0506 (9) | |
H46 | 0.5976 | 0.4435 | 0.1297 | 0.061* | |
O51 | 0.872 (3) | 0.5861 (11) | 0.5839 (11) | 0.411 (15) | |
C52 | 0.870 (2) | 0.6283 (7) | 0.5277 (18) | 0.223 (9) | |
H52A | 0.9692 | 0.6370 | 0.5121 | 0.267* | |
H52B | 0.8259 | 0.6575 | 0.5551 | 0.267* | |
C53 | 0.776 (3) | 0.6104 (11) | 0.4466 (11) | 0.253 (10) | |
H53A | 0.7123 | 0.6372 | 0.4221 | 0.303* | |
H53B | 0.8356 | 0.5969 | 0.4009 | 0.303* | |
C54 | 0.688 (2) | 0.5686 (10) | 0.491 (2) | 0.39 (2) | |
H54A | 0.6271 | 0.5803 | 0.5374 | 0.470* | |
H54B | 0.6333 | 0.5460 | 0.4496 | 0.470* | |
C55 | 0.840 (3) | 0.5499 (6) | 0.5216 (17) | 0.36 (2) | |
H55A | 0.8369 | 0.5161 | 0.5471 | 0.429* | |
H55B | 0.9081 | 0.5505 | 0.4746 | 0.429* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.062 (3) | 0.062 (3) | 0.060 (3) | 0.015 (2) | −0.011 (2) | −0.023 (2) |
C11 | 0.054 (2) | 0.054 (2) | 0.049 (2) | 0.015 (2) | −0.0098 (18) | −0.0136 (18) |
C12 | 0.054 (2) | 0.049 (2) | 0.050 (2) | 0.0048 (18) | −0.0063 (18) | −0.0065 (17) |
O12 | 0.071 (2) | 0.065 (2) | 0.075 (2) | −0.0152 (16) | 0.0061 (17) | −0.0183 (16) |
C17 | 0.156 (7) | 0.057 (3) | 0.141 (6) | −0.024 (4) | 0.034 (5) | 0.008 (4) |
C13 | 0.051 (2) | 0.049 (2) | 0.0374 (19) | 0.0029 (17) | −0.0003 (16) | −0.0018 (16) |
C14 | 0.054 (2) | 0.054 (2) | 0.0371 (19) | 0.0000 (18) | 0.0030 (16) | −0.0083 (16) |
C15 | 0.056 (2) | 0.056 (2) | 0.043 (2) | 0.0076 (19) | 0.0077 (18) | −0.0003 (18) |
Br15 | 0.0778 (4) | 0.0876 (4) | 0.0686 (3) | −0.0126 (3) | 0.0313 (3) | −0.0090 (3) |
C16 | 0.059 (3) | 0.063 (3) | 0.037 (2) | 0.017 (2) | 0.0004 (18) | −0.0091 (18) |
C2 | 0.058 (3) | 0.067 (3) | 0.042 (2) | −0.012 (2) | 0.0071 (18) | −0.0050 (19) |
C21 | 0.047 (2) | 0.056 (2) | 0.0323 (17) | −0.0022 (17) | 0.0068 (15) | 0.0002 (16) |
C22 | 0.055 (2) | 0.048 (2) | 0.043 (2) | −0.0010 (18) | 0.0085 (18) | 0.0027 (16) |
O22 | 0.089 (2) | 0.0460 (17) | 0.072 (2) | 0.0023 (16) | −0.0009 (18) | −0.0014 (14) |
C27 | 0.138 (6) | 0.062 (3) | 0.071 (3) | −0.026 (3) | −0.018 (3) | 0.013 (3) |
C23 | 0.046 (2) | 0.052 (2) | 0.0386 (19) | −0.0041 (17) | 0.0018 (16) | 0.0071 (16) |
C24 | 0.051 (2) | 0.050 (2) | 0.043 (2) | −0.0095 (18) | −0.0022 (17) | 0.0034 (17) |
C25 | 0.052 (2) | 0.046 (2) | 0.043 (2) | −0.0016 (17) | 0.0036 (17) | 0.0077 (16) |
Br25 | 0.0805 (4) | 0.0490 (2) | 0.0858 (3) | 0.0045 (2) | −0.0107 (3) | 0.0024 (2) |
C26 | 0.049 (2) | 0.059 (2) | 0.0368 (19) | −0.0010 (18) | 0.0022 (16) | 0.0082 (17) |
C3 | 0.053 (3) | 0.057 (2) | 0.055 (2) | −0.0002 (19) | −0.0027 (19) | 0.0135 (19) |
C31 | 0.050 (2) | 0.048 (2) | 0.0379 (19) | −0.0024 (17) | −0.0093 (16) | 0.0020 (16) |
C32 | 0.047 (2) | 0.047 (2) | 0.047 (2) | 0.0023 (17) | −0.0051 (17) | −0.0057 (17) |
O32 | 0.065 (2) | 0.0598 (18) | 0.0621 (18) | 0.0139 (15) | 0.0101 (15) | −0.0004 (14) |
C37 | 0.058 (4) | 0.128 (6) | 0.125 (5) | 0.028 (4) | 0.017 (3) | 0.022 (4) |
C33 | 0.058 (2) | 0.040 (2) | 0.040 (2) | −0.0007 (17) | −0.0103 (17) | −0.0010 (15) |
C34 | 0.062 (3) | 0.050 (2) | 0.0376 (19) | −0.0012 (19) | −0.0006 (17) | −0.0003 (16) |
C35 | 0.063 (3) | 0.059 (3) | 0.040 (2) | 0.014 (2) | −0.0048 (18) | −0.0050 (18) |
Br35 | 0.1185 (5) | 0.1044 (4) | 0.0561 (3) | 0.0538 (4) | 0.0197 (3) | 0.0066 (3) |
C36 | 0.065 (3) | 0.046 (2) | 0.043 (2) | 0.0094 (19) | −0.0092 (18) | 0.0008 (17) |
C4 | 0.068 (3) | 0.039 (2) | 0.047 (2) | −0.0005 (18) | −0.0093 (19) | 0.0011 (16) |
C41 | 0.057 (2) | 0.041 (2) | 0.0397 (19) | 0.0005 (17) | −0.0015 (17) | 0.0020 (15) |
C42 | 0.052 (2) | 0.048 (2) | 0.042 (2) | 0.0032 (17) | −0.0015 (17) | −0.0017 (16) |
O42 | 0.0512 (17) | 0.0589 (17) | 0.0542 (16) | 0.0023 (13) | −0.0062 (13) | −0.0057 (13) |
C47 | 0.069 (3) | 0.084 (3) | 0.062 (3) | 0.005 (3) | −0.016 (2) | 0.004 (3) |
C43 | 0.052 (2) | 0.052 (2) | 0.044 (2) | 0.0049 (18) | 0.0000 (18) | −0.0096 (17) |
C44 | 0.056 (3) | 0.052 (2) | 0.055 (2) | 0.0013 (19) | −0.0045 (19) | −0.0134 (19) |
C45 | 0.053 (2) | 0.049 (2) | 0.057 (2) | 0.0027 (18) | −0.0046 (19) | −0.0023 (19) |
Br45 | 0.0588 (3) | 0.0644 (3) | 0.1109 (4) | 0.0088 (2) | −0.0254 (3) | −0.0122 (3) |
C46 | 0.056 (2) | 0.041 (2) | 0.054 (2) | 0.0031 (18) | 0.0018 (19) | −0.0006 (17) |
O51 | 0.60 (4) | 0.37 (3) | 0.258 (16) | 0.23 (3) | −0.029 (19) | −0.022 (19) |
C52 | 0.221 (17) | 0.149 (12) | 0.31 (3) | −0.043 (11) | 0.119 (17) | −0.053 (14) |
C53 | 0.26 (2) | 0.32 (3) | 0.176 (14) | 0.108 (19) | 0.009 (15) | 0.032 (17) |
C54 | 0.22 (2) | 0.33 (3) | 0.63 (5) | −0.08 (2) | 0.16 (3) | −0.34 (4) |
C55 | 0.51 (5) | 0.117 (12) | 0.47 (4) | 0.032 (19) | 0.27 (4) | 0.057 (18) |
Geometric parameters (Å, º) top
C1—C11 | 1.510 (6) | C32—C33 | 1.399 (6) |
C1—C43i | 1.519 (6) | O32—C37 | 1.422 (7) |
C1—H1A | 0.9700 | C37—H37A | 0.9600 |
C1—H1B | 0.9700 | C37—H37B | 0.9600 |
C11—C16 | 1.386 (7) | C37—H37C | 0.9600 |
C11—C12 | 1.397 (6) | C33—C34 | 1.368 (6) |
C12—O12 | 1.375 (5) | C33—C4 | 1.510 (5) |
C12—C13 | 1.393 (6) | C34—C35 | 1.396 (6) |
O12—C17 | 1.406 (7) | C34—H34 | 0.9300 |
C17—H17A | 0.9600 | C35—C36 | 1.376 (6) |
C17—H17B | 0.9600 | C35—Br35 | 1.896 (4) |
C17—H17C | 0.9600 | C36—H36 | 0.9300 |
C13—C14 | 1.377 (6) | C4—C41 | 1.514 (5) |
C13—C2 | 1.526 (5) | C4—H4A | 0.9700 |
C14—C15 | 1.381 (5) | C4—H4B | 0.9700 |
C14—H14 | 0.9300 | C41—C46 | 1.381 (6) |
C15—C16 | 1.375 (6) | C41—C42 | 1.397 (6) |
C15—Br15 | 1.897 (4) | C42—O42 | 1.383 (5) |
C16—H16 | 0.9300 | C42—C43 | 1.398 (6) |
C2—C21 | 1.504 (6) | O42—C47 | 1.414 (5) |
C2—H2A | 0.9700 | C47—H47A | 0.9600 |
C2—H2B | 0.9700 | C47—H47B | 0.9600 |
C21—C26 | 1.382 (6) | C47—H47C | 0.9600 |
C21—C22 | 1.395 (6) | C43—C44 | 1.384 (6) |
C22—O22 | 1.376 (5) | C43—C1i | 1.519 (6) |
C22—C23 | 1.394 (6) | C44—C45 | 1.385 (6) |
O22—C27 | 1.442 (7) | C44—H44 | 0.9300 |
C27—H27A | 0.9600 | C45—C46 | 1.376 (6) |
C27—H27B | 0.9600 | C45—Br45 | 1.895 (4) |
C27—H27C | 0.9600 | C46—H46 | 0.9300 |
C23—C24 | 1.383 (6) | O51—C52 | 1.396 (9) |
C23—C3 | 1.512 (6) | O51—C55 | 1.359 (10) |
C24—C25 | 1.379 (6) | C52—C53 | 1.529 (9) |
C24—H24 | 0.9300 | C52—H52A | 0.9700 |
C25—C26 | 1.377 (6) | C52—H52B | 0.9700 |
C25—Br25 | 1.896 (4) | C53—C54 | 1.532 (10) |
C26—H26 | 0.9300 | C53—H53A | 0.9700 |
C3—C31 | 1.508 (6) | C53—H53B | 0.9700 |
C3—H3A | 0.9700 | C54—C55 | 1.513 (10) |
C3—H3B | 0.9700 | C54—H54A | 0.9700 |
C31—C36 | 1.393 (6) | C54—H54B | 0.9700 |
C31—C32 | 1.398 (6) | C55—H55A | 0.9700 |
C32—O32 | 1.377 (5) | C55—H55B | 0.9700 |
| | | |
C11—C1—C43i | 116.5 (4) | O32—C37—H37A | 109.5 |
C11—C1—H1A | 108.2 | O32—C37—H37B | 109.5 |
C43i—C1—H1A | 108.2 | H37A—C37—H37B | 109.5 |
C11—C1—H1B | 108.2 | O32—C37—H37C | 109.5 |
C43i—C1—H1B | 108.2 | H37A—C37—H37C | 109.5 |
H1A—C1—H1B | 107.3 | H37B—C37—H37C | 109.5 |
C16—C11—C12 | 118.0 (4) | C34—C33—C32 | 118.7 (4) |
C16—C11—C1 | 120.4 (4) | C34—C33—C4 | 121.4 (4) |
C12—C11—C1 | 121.3 (4) | C32—C33—C4 | 119.8 (4) |
O12—C12—C13 | 117.9 (4) | C33—C34—C35 | 120.2 (4) |
O12—C12—C11 | 120.1 (4) | C33—C34—H34 | 119.9 |
C13—C12—C11 | 121.8 (4) | C35—C34—H34 | 119.9 |
C12—O12—C17 | 114.8 (5) | C36—C35—C34 | 120.6 (4) |
O12—C17—H17A | 109.5 | C36—C35—Br35 | 120.5 (3) |
O12—C17—H17B | 109.5 | C34—C35—Br35 | 118.9 (3) |
H17A—C17—H17B | 109.5 | C35—C36—C31 | 120.9 (4) |
O12—C17—H17C | 109.5 | C35—C36—H36 | 119.5 |
H17A—C17—H17C | 109.5 | C31—C36—H36 | 119.5 |
H17B—C17—H17C | 109.5 | C33—C4—C41 | 112.7 (3) |
C14—C13—C12 | 118.8 (4) | C33—C4—H4A | 109.1 |
C14—C13—C2 | 122.0 (3) | C41—C4—H4A | 109.1 |
C12—C13—C2 | 119.1 (4) | C33—C4—H4B | 109.1 |
C13—C14—C15 | 119.8 (4) | C41—C4—H4B | 109.1 |
C13—C14—H14 | 120.1 | H4A—C4—H4B | 107.8 |
C15—C14—H14 | 120.1 | C46—C41—C42 | 118.0 (4) |
C16—C15—C14 | 121.4 (4) | C46—C41—C4 | 120.9 (4) |
C16—C15—Br15 | 119.2 (3) | C42—C41—C4 | 121.1 (4) |
C14—C15—Br15 | 119.3 (3) | O42—C42—C43 | 118.1 (3) |
C15—C16—C11 | 120.2 (4) | O42—C42—C41 | 119.7 (3) |
C15—C16—H16 | 119.9 | C43—C42—C41 | 122.1 (4) |
C11—C16—H16 | 119.9 | C42—O42—C47 | 115.8 (3) |
C21—C2—C13 | 114.2 (3) | O42—C47—H47A | 109.5 |
C21—C2—H2A | 108.7 | O42—C47—H47B | 109.5 |
C13—C2—H2A | 108.7 | H47A—C47—H47B | 109.5 |
C21—C2—H2B | 108.7 | O42—C47—H47C | 109.5 |
C13—C2—H2B | 108.7 | H47A—C47—H47C | 109.5 |
H2A—C2—H2B | 107.6 | H47B—C47—H47C | 109.5 |
C26—C21—C22 | 118.7 (4) | C44—C43—C42 | 118.3 (4) |
C26—C21—C2 | 120.2 (4) | C44—C43—C1i | 123.5 (4) |
C22—C21—C2 | 121.1 (4) | C42—C43—C1i | 118.2 (4) |
O22—C22—C23 | 119.1 (4) | C45—C44—C43 | 119.7 (4) |
O22—C22—C21 | 119.0 (4) | C45—C44—H44 | 120.1 |
C23—C22—C21 | 121.7 (4) | C43—C44—H44 | 120.1 |
C22—O22—C27 | 115.2 (4) | C46—C45—C44 | 121.4 (4) |
O22—C27—H27A | 109.5 | C46—C45—Br45 | 118.5 (3) |
O22—C27—H27B | 109.5 | C44—C45—Br45 | 120.0 (3) |
H27A—C27—H27B | 109.5 | C45—C46—C41 | 120.4 (4) |
O22—C27—H27C | 109.5 | C45—C46—H46 | 119.8 |
H27A—C27—H27C | 109.5 | C41—C46—H46 | 119.8 |
H27B—C27—H27C | 109.5 | C52—O51—C55 | 98.1 (14) |
C24—C23—C22 | 118.0 (4) | O51—C52—C53 | 103.2 (13) |
C24—C23—C3 | 120.5 (4) | O51—C52—H52A | 111.1 |
C22—C23—C3 | 121.5 (4) | C53—C52—H52A | 111.1 |
C25—C24—C23 | 120.6 (4) | O51—C52—H52B | 111.1 |
C25—C24—H24 | 119.7 | C53—C52—H52B | 111.1 |
C23—C24—H24 | 119.7 | H52A—C52—H52B | 109.1 |
C26—C25—C24 | 121.0 (4) | C54—C53—C52 | 98.9 (13) |
C26—C25—Br25 | 120.1 (3) | C54—C53—H53A | 112.0 |
C24—C25—Br25 | 119.0 (3) | C52—C53—H53A | 112.0 |
C25—C26—C21 | 120.0 (4) | C54—C53—H53B | 112.0 |
C25—C26—H26 | 120.0 | C52—C53—H53B | 112.0 |
C21—C26—H26 | 120.0 | H53A—C53—H53B | 109.7 |
C31—C3—C23 | 114.1 (3) | C55—C54—C53 | 83.1 (12) |
C31—C3—H3A | 108.7 | C55—C54—H54A | 114.8 |
C23—C3—H3A | 108.7 | C53—C54—H54A | 114.8 |
C31—C3—H3B | 108.7 | C55—C54—H54B | 114.8 |
C23—C3—H3B | 108.7 | C53—C54—H54B | 114.8 |
H3A—C3—H3B | 107.6 | H54A—C54—H54B | 111.9 |
C36—C31—C32 | 117.3 (4) | O51—C55—C54 | 98.1 (18) |
C36—C31—C3 | 121.3 (4) | O51—C55—H55A | 112.1 |
C32—C31—C3 | 121.4 (4) | C54—C55—H55A | 112.1 |
O32—C32—C33 | 118.1 (4) | O51—C55—H55B | 112.1 |
O32—C32—C31 | 119.4 (4) | C54—C55—H55B | 112.1 |
C33—C32—C31 | 122.3 (4) | H55A—C55—H55B | 109.8 |
C32—O32—C37 | 114.5 (4) | | |
| | | |
C43i—C1—C11—C16 | −76.3 (6) | C36—C31—C32—O32 | −177.8 (4) |
C43i—C1—C11—C12 | 110.3 (5) | C3—C31—C32—O32 | 1.4 (6) |
C16—C11—C12—O12 | −176.0 (4) | C36—C31—C32—C33 | −2.6 (6) |
C1—C11—C12—O12 | −2.4 (6) | C3—C31—C32—C33 | 176.5 (4) |
C16—C11—C12—C13 | −1.3 (6) | C33—C32—O32—C37 | 98.4 (5) |
C1—C11—C12—C13 | 172.2 (4) | C31—C32—O32—C37 | −86.2 (5) |
C13—C12—O12—C17 | 105.0 (5) | O32—C32—C33—C34 | 177.1 (4) |
C11—C12—O12—C17 | −80.1 (6) | C31—C32—C33—C34 | 1.9 (6) |
O12—C12—C13—C14 | 176.7 (4) | O32—C32—C33—C4 | 0.7 (5) |
C11—C12—C13—C14 | 2.0 (6) | C31—C32—C33—C4 | −174.6 (4) |
O12—C12—C13—C2 | −0.1 (6) | C32—C33—C34—C35 | −0.1 (6) |
C11—C12—C13—C2 | −174.9 (4) | C4—C33—C34—C35 | 176.3 (4) |
C12—C13—C14—C15 | −1.5 (6) | C33—C34—C35—C36 | −0.9 (6) |
C2—C13—C14—C15 | 175.3 (4) | C33—C34—C35—Br35 | 179.8 (3) |
C13—C14—C15—C16 | 0.4 (6) | C34—C35—C36—C31 | 0.2 (6) |
C13—C14—C15—Br15 | −177.2 (3) | Br35—C35—C36—C31 | 179.4 (3) |
C14—C15—C16—C11 | 0.2 (6) | C32—C31—C36—C35 | 1.5 (6) |
Br15—C15—C16—C11 | 177.9 (3) | C3—C31—C36—C35 | −177.6 (4) |
C12—C11—C16—C15 | 0.2 (6) | C34—C33—C4—C41 | −103.3 (4) |
C1—C11—C16—C15 | −173.4 (4) | C32—C33—C4—C41 | 73.1 (5) |
C14—C13—C2—C21 | 18.9 (6) | C33—C4—C41—C46 | 34.7 (6) |
C12—C13—C2—C21 | −164.3 (4) | C33—C4—C41—C42 | −146.0 (4) |
C13—C2—C21—C26 | −93.2 (5) | C46—C41—C42—O42 | −176.0 (4) |
C13—C2—C21—C22 | 86.2 (5) | C4—C41—C42—O42 | 4.7 (6) |
C26—C21—C22—O22 | 177.5 (4) | C46—C41—C42—C43 | 0.7 (6) |
C2—C21—C22—O22 | −1.9 (6) | C4—C41—C42—C43 | −178.7 (4) |
C26—C21—C22—C23 | 1.7 (6) | C43—C42—O42—C47 | 97.0 (5) |
C2—C21—C22—C23 | −177.7 (4) | C41—C42—O42—C47 | −86.2 (5) |
C23—C22—O22—C27 | −94.0 (5) | O42—C42—C43—C44 | 175.7 (4) |
C21—C22—O22—C27 | 90.1 (5) | C41—C42—C43—C44 | −1.0 (6) |
O22—C22—C23—C24 | −178.1 (4) | O42—C42—C43—C1i | −3.8 (6) |
C21—C22—C23—C24 | −2.3 (6) | C41—C42—C43—C1i | 179.5 (4) |
O22—C22—C23—C3 | 1.7 (6) | C42—C43—C44—C45 | 0.7 (6) |
C21—C22—C23—C3 | 177.4 (4) | C1i—C43—C44—C45 | −179.9 (4) |
C22—C23—C24—C25 | 0.5 (6) | C43—C44—C45—C46 | 0.0 (7) |
C3—C23—C24—C25 | −179.2 (4) | C43—C44—C45—Br45 | 179.6 (3) |
C23—C24—C25—C26 | 1.8 (6) | C44—C45—C46—C41 | −0.4 (7) |
C23—C24—C25—Br25 | −176.6 (3) | Br45—C45—C46—C41 | −179.9 (3) |
C24—C25—C26—C21 | −2.5 (6) | C42—C41—C46—C45 | 0.0 (6) |
Br25—C25—C26—C21 | 176.0 (3) | C4—C41—C46—C45 | 179.4 (4) |
C22—C21—C26—C25 | 0.7 (6) | C55—O51—C52—C53 | 22 (2) |
C2—C21—C26—C25 | −179.9 (4) | O51—C52—C53—C54 | 24 (2) |
C24—C23—C3—C31 | −96.9 (5) | C52—C53—C54—C55 | −53.1 (15) |
C22—C23—C3—C31 | 83.3 (5) | C52—O51—C55—C54 | −63 (2) |
C23—C3—C31—C36 | 44.5 (5) | C53—C54—C55—O51 | 73.4 (16) |
C23—C3—C31—C32 | −134.6 (4) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Comparison of the torsion angles (°) of (I) and (Ib) top | Compound (I) | Compound (Ib) |
C32-C31-C3-C23 | -134.6 (4) | -136.2 |
C31-C3-C23-C22 | 83.3 (5) | 92.1 |
C42-C41-C4-C33 | -146.0 (4) | -144.3 |
C41-C4-C33-C32 | 73.1 (5) | 72.6 |
C22-C21-C2-C13 | 86.2 (5) | 95.5 |
C21-C2-C13-C12 | -164.3 (4) | -174.9 |
C12-C11-C1-C43i | 110.3 (5) | 92.9 |
C11-C1-C43i-C42i | -175.2 (4) | -165.3 |
Symmetry code: (i) 1-x, 1-y, 1-z. |