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In the title adduct, C28H24B2F6O4·C28H32B2F6O4·C6H14, cis isomers of 2-catecholboryl-1-pinacolboryl- and bis(1,2-pinacolboryl)-1,2-bis[4-(trifluoromethyl)phenyl]ethene substitute one another isomorphously in a 1:1 ratio. The molecule has no crystallographic symmetry, with one olefinic site shared equally between superimposed pinacol- and catecholboryls, and the other occupied solely by a (disordered) pinacolboryl. CF3 groups and hexane solvent molecules are also disordered.
Supporting information
CCDC reference: 647295
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.004 Å
Some non-H atoms missing
- Disorder in main residue
- R factor = 0.074
- wR factor = 0.257
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C28
| Author Response: In fact, the ADP of C28 are quite normal. They look small in
comparison with those of the attached fluorines, which are probably
disordered, although the disorder could not be resolved (as stated in
the comments)
|
Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 2
PLAT213_ALERT_2_B Atom F3A has ADP max/min Ratio ............. 4.60 prola
PLAT301_ALERT_3_B Main Residue Disorder ......................... 29.00 Perc.
Alert level C
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
calculated from the _atom_site* data lies outside
the range 0.99 <> 1.01
From the CIF: _cell_formula_units_Z 2
From the CIF: _chemical_formula_weight 1214.42
TEST: Calculate formula weight from _atom_site_*
atom mass num sum
C 12.01 59.00 708.65
H 1.01 56.00 56.45
B 10.81 4.00 43.24
O 16.00 8.00 127.99
F 19.00 12.00 227.98
Calculated formula weight 1164.31
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.257
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT043_ALERT_1_C Check Reported Molecular Weight ................ 1214.42
PLAT044_ALERT_1_C Calculated and Reported Dx Differ .............. ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT084_ALERT_2_C High R2 Value .................................. 0.26
PLAT128_ALERT_4_C Non-standard setting of Space group P2/c .... P2/n
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.63 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C11
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27
| Author Response: In fact, the ADP of C28 are quite normal. They look small in
comparison with those of the attached fluorines, which are probably
disordered, although the disorder could not be resolved (as stated in
the comments)
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O4A
| Author Response: In fact, the ADP of C28 are quite normal. They look small in
comparison with those of the attached fluorines, which are probably
disordered, although the disorder could not be resolved (as stated in
the comments)
|
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C3S
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.15
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 40.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
Alert level G
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C62 H70 B4 F12 O8
Atom count from the _atom_site data: C59 H56 B4 F12 O8
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
symmetry error - see SYMMG tests
From the CIF: _cell_formula_units_Z 2
From the CIF: _chemical_formula_sum C62 H70 B4 F12 O8
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 124.00 118.00 6.00
H 140.00 112.00 28.00
B 8.00 8.00 0.00
F 24.00 24.00 0.00
O 16.00 16.00 0.00
1 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
18 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
12 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
cis-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-bis[4-
(trifluoromethyl)phenyl]ethene–
cis-2-(1,3,2-benzodioxaborolan-2-yl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-1,2-bis[4-(trifluoromethyl)phenyl]ethene–hexane (1/1/1)
top
Crystal data top
C28H24B2F6O4·C28H32B2F6O4·C6H14 | F(000) = 1268 |
Mr = 1214.42 | Dx = 1.359 Mg m−3 |
Monoclinic, P2/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yac | Cell parameters from 995 reflections |
a = 16.598 (2) Å | θ = 12–25° |
b = 6.4631 (5) Å | µ = 0.11 mm−1 |
c = 28.535 (3) Å | T = 120 K |
β = 104.25 (1)° | Prism, colourless |
V = 2966.9 (5) Å3 | 0.22 × 0.15 × 0.15 mm |
Z = 2 | |
Data collection top
Bruker SMART 6000 CCD area-detector diffractometer | 3598 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.053 |
Graphite monochromator | θmax = 27.5°, θmin = 1.6° |
Detector resolution: 5.6 pixels mm-1 | h = −21→21 |
ω scans | k = −8→8 |
31871 measured reflections | l = −37→37 |
6813 independent reflections | |
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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.258 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1336P)2 + 0.6651P] where P = (Fo2 + 2Fc2)/3 |
6812 reflections | (Δ/σ)max = 0.005 |
414 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
Special details top
Experimental. The data collection nominally covered a full sphere of reciprocal space, by a
combination of 3 runs of 600 ω-scans each (scan width 0.3° ω, 20 s
exposure); every run at a different φ angle. The crystal to detector distance
was 4.87 cm. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.27231 (12) | 0.1693 (3) | 0.65866 (7) | 0.0514 (5) | |
O2A | 0.3514 (2) | 0.4620 (5) | 0.68626 (14) | 0.0386 (8)* | 0.50 |
O3A | 0.3947 (4) | −0.0613 (10) | 0.5458 (2) | 0.0488 (16)* | 0.33 |
O4A | 0.3630 (4) | 0.2653 (9) | 0.57364 (19) | 0.0364 (13)* | 0.33 |
O2B | 0.3541 (2) | 0.4467 (5) | 0.66019 (14) | 0.0400 (8)* | 0.50 |
O3B | 0.4251 (2) | −0.0121 (5) | 0.54352 (11) | 0.0477 (8)* | 0.67 |
O4B | 0.3421 (2) | 0.1917 (6) | 0.57598 (12) | 0.0547 (9)* | 0.67 |
C1A | 0.2138 (3) | 0.3421 (8) | 0.6730 (2) | 0.0402 (12)* | 0.50 |
C2A | 0.2664 (3) | 0.5452 (8) | 0.6760 (2) | 0.0392 (11)* | 0.50 |
C3A | 0.2013 (4) | 0.2699 (10) | 0.7210 (2) | 0.0554 (14)* | 0.50 |
H31A | 0.1656 | 0.3680 | 0.7326 | 0.083* | 0.50 |
H32A | 0.1748 | 0.1334 | 0.7167 | 0.083* | 0.50 |
H33A | 0.2552 | 0.2602 | 0.7446 | 0.083* | 0.50 |
C4A | 0.1338 (5) | 0.3489 (12) | 0.6328 (3) | 0.050 (2)* | 0.50 |
H41A | 0.0966 | 0.4550 | 0.6401 | 0.075* | 0.50 |
H42A | 0.1467 | 0.3808 | 0.6019 | 0.075* | 0.50 |
H43A | 0.1067 | 0.2134 | 0.6308 | 0.075* | 0.50 |
C5A | 0.2589 (3) | 0.6894 (8) | 0.71607 (19) | 0.0451 (12)* | 0.50 |
H51A | 0.2939 | 0.8113 | 0.7159 | 0.068* | 0.50 |
H52A | 0.2008 | 0.7326 | 0.7109 | 0.068* | 0.50 |
H53A | 0.2767 | 0.6188 | 0.7473 | 0.068* | 0.50 |
C6A | 0.2534 (4) | 0.6572 (9) | 0.6281 (2) | 0.0480 (14)* | 0.50 |
H61A | 0.2877 | 0.7825 | 0.6323 | 0.072* | 0.50 |
H62A | 0.2695 | 0.5660 | 0.6045 | 0.072* | 0.50 |
H63A | 0.1947 | 0.6952 | 0.6164 | 0.072* | 0.50 |
C7A | 0.3337 (8) | 0.044 (2) | 0.5061 (4) | 0.058 (3) | 0.33 |
C8A | 0.3390 (8) | 0.2655 (19) | 0.5196 (4) | 0.057 (3) | 0.33 |
C9A | 0.4073 (8) | 0.386 (2) | 0.5032 (5) | 0.072 (4)* | 0.33 |
H9A1 | 0.4588 | 0.3053 | 0.5128 | 0.109* | 0.33 |
H9A2 | 0.4158 | 0.5223 | 0.5185 | 0.109* | 0.33 |
H9A3 | 0.3917 | 0.4015 | 0.4680 | 0.109* | 0.33 |
C10A | 0.2499 (11) | −0.057 (3) | 0.5084 (6) | 0.090 (6)* | 0.33 |
H101 | 0.2389 | −0.0139 | 0.5392 | 0.135* | 0.33 |
H102 | 0.2537 | −0.2087 | 0.5077 | 0.135* | 0.33 |
H103 | 0.2045 | −0.0106 | 0.4816 | 0.135* | 0.33 |
C1B | 0.2245 (3) | 0.3172 (8) | 0.6513 (2) | 0.0407 (12)* | 0.50 |
C2B | 0.2701 (3) | 0.4957 (8) | 0.6515 (2) | 0.0384 (11)* | 0.50 |
C3B | 0.2325 (4) | 0.6862 (10) | 0.6439 (2) | 0.0491 (14)* | 0.50 |
H3B | 0.2641 | 0.8085 | 0.6435 | 0.059* | 0.50 |
C4B | 0.1473 (4) | 0.6895 (10) | 0.6362 (2) | 0.0570 (15)* | 0.50 |
H4B | 0.1189 | 0.8182 | 0.6304 | 0.068* | 0.50 |
C5B | 0.1022 (4) | 0.5110 (10) | 0.6363 (2) | 0.0587 (15)* | 0.50 |
H5B | 0.0436 | 0.5237 | 0.6309 | 0.070* | 0.50 |
C6B | 0.1372 (5) | 0.3160 (12) | 0.6448 (3) | 0.047 (2)* | 0.50 |
H6B | 0.1062 | 0.1933 | 0.6459 | 0.057* | 0.50 |
C7B | 0.3738 (4) | 0.1075 (10) | 0.50305 (17) | 0.0506 (13) | 0.67 |
C8B | 0.3001 (3) | 0.1781 (11) | 0.52440 (16) | 0.0545 (12) | 0.67 |
C9B | 0.4275 (3) | 0.2869 (9) | 0.49474 (17) | 0.0616 (13) | 0.67 |
H9B1 | 0.4418 | 0.3733 | 0.5238 | 0.092* | 0.67 |
H9B2 | 0.3974 | 0.3702 | 0.4673 | 0.092* | 0.67 |
H9B3 | 0.4785 | 0.2324 | 0.4879 | 0.092* | 0.67 |
C10B | 0.2335 (3) | 0.0164 (12) | 0.52078 (18) | 0.0660 (16) | 0.67 |
H104 | 0.2585 | −0.1170 | 0.5326 | 0.099* | 0.67 |
H105 | 0.2019 | 0.0018 | 0.4871 | 0.099* | 0.67 |
H106 | 0.1963 | 0.0613 | 0.5406 | 0.099* | 0.67 |
C11 | 0.3511 (3) | −0.0266 (6) | 0.45949 (10) | 0.0737 (10) | |
H111 | 0.3019 | −0.0041 | 0.4328 | 0.111* | 0.33 |
H112 | 0.3979 | 0.0529 | 0.4536 | 0.111* | 0.33 |
H113 | 0.3652 | −0.1741 | 0.4616 | 0.111* | 0.33 |
H114 | 0.3160 | −0.1392 | 0.4663 | 0.111* | 0.67 |
H115 | 0.4021 | −0.0844 | 0.4534 | 0.111* | 0.67 |
H116 | 0.3208 | 0.0502 | 0.4310 | 0.111* | 0.67 |
C12 | 0.2622 (2) | 0.3874 (7) | 0.50620 (12) | 0.0757 (11) | |
H121 | 0.2545 | 0.4384 | 0.4730 | 0.114* | 0.33 |
H122 | 0.2148 | 0.3003 | 0.5082 | 0.114* | 0.33 |
H123 | 0.2660 | 0.5050 | 0.5283 | 0.114* | 0.33 |
H124 | 0.3063 | 0.4902 | 0.5083 | 0.114* | 0.67 |
H125 | 0.2260 | 0.4296 | 0.5269 | 0.114* | 0.67 |
H126 | 0.2294 | 0.3772 | 0.4726 | 0.114* | 0.67 |
C13 | 0.42987 (17) | 0.1048 (4) | 0.67399 (9) | 0.0449 (6) | |
C14 | 0.45510 (17) | 0.0135 (5) | 0.63759 (9) | 0.0473 (7) | |
C15 | 0.47071 (16) | 0.0623 (4) | 0.72607 (9) | 0.0447 (6) | |
C16 | 0.4699 (2) | −0.1361 (5) | 0.74442 (10) | 0.0548 (8) | |
H16 | 0.4444 | −0.2461 | 0.7240 | 0.066* | |
C17 | 0.5066 (2) | −0.1734 (6) | 0.79293 (11) | 0.0681 (10) | |
H17 | 0.5054 | −0.3088 | 0.8057 | 0.082* | |
C18 | 0.5442 (2) | −0.0138 (7) | 0.82253 (10) | 0.0681 (10) | |
C19 | 0.54474 (19) | 0.1830 (6) | 0.80464 (11) | 0.0644 (9) | |
H19 | 0.5699 | 0.2928 | 0.8252 | 0.077* | |
C20 | 0.50789 (17) | 0.2221 (5) | 0.75642 (10) | 0.0543 (8) | |
H20 | 0.5082 | 0.3587 | 0.7442 | 0.065* | |
C21 | 0.52927 (17) | −0.1239 (5) | 0.64603 (9) | 0.0467 (7) | |
C22 | 0.60631 (18) | −0.0535 (5) | 0.67187 (10) | 0.0524 (7) | |
H22 | 0.6111 | 0.0823 | 0.6850 | 0.063* | |
C23 | 0.67572 (19) | −0.1793 (5) | 0.67899 (11) | 0.0561 (8) | |
H23 | 0.7284 | −0.1274 | 0.6959 | 0.067* | |
C24 | 0.66931 (18) | −0.3775 (5) | 0.66107 (10) | 0.0529 (7) | |
C25 | 0.59194 (19) | −0.4509 (5) | 0.63526 (10) | 0.0528 (7) | |
H25 | 0.5869 | −0.5884 | 0.6231 | 0.063* | |
C26 | 0.52339 (19) | −0.3253 (5) | 0.62767 (9) | 0.0506 (7) | |
H26 | 0.4712 | −0.3753 | 0.6094 | 0.061* | |
C27 | 0.5847 (3) | −0.0540 (10) | 0.87461 (14) | 0.1012 (18) | |
C28 | 0.7439 (2) | −0.5130 (6) | 0.66834 (14) | 0.0688 (9) | |
F1A | 0.6672 (2) | −0.0624 (8) | 0.88240 (10) | 0.1136 (13) | 0.80 |
F2A | 0.5704 (3) | −0.2455 (10) | 0.88921 (11) | 0.1473 (19) | 0.80 |
F3A | 0.5692 (5) | 0.0843 (13) | 0.90304 (11) | 0.207 (4) | 0.80 |
F1B | 0.5219 (10) | −0.095 (3) | 0.8982 (6) | 0.095 (4)* | 0.20 |
F2B | 0.6159 (13) | 0.111 (3) | 0.9010 (8) | 0.117 (7)* | 0.20 |
F3B | 0.6319 (17) | −0.186 (4) | 0.8872 (8) | 0.138 (7)* | 0.20 |
F4 | 0.81306 (12) | −0.4276 (4) | 0.69323 (11) | 0.1000 (8) | |
F5 | 0.73803 (15) | −0.6821 (4) | 0.69117 (16) | 0.1518 (16) | |
F6 | 0.7605 (2) | −0.5677 (7) | 0.62779 (12) | 0.1741 (19) | |
B1 | 0.3514 (2) | 0.2468 (5) | 0.66656 (12) | 0.0515 (8) | |
B2 | 0.4060 (2) | 0.0668 (6) | 0.58455 (11) | 0.0495 (8) | |
C1S | 0.0000 | 0.5000 | 0.5000 | 0.168 (4) | |
C2S | −0.0205 (6) | 0.891 (2) | 0.4957 (3) | 0.119 (4) | 0.50 |
C3S | 0.0364 (7) | 0.714 (3) | 0.5062 (4) | 0.127 (4) | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0453 (11) | 0.0544 (12) | 0.0532 (11) | −0.0115 (9) | 0.0093 (9) | −0.0059 (9) |
C7A | 0.054 (7) | 0.068 (8) | 0.042 (5) | 0.006 (6) | −0.006 (5) | 0.004 (5) |
C8A | 0.057 (7) | 0.070 (7) | 0.041 (5) | 0.005 (6) | 0.005 (5) | 0.006 (5) |
C7B | 0.051 (3) | 0.069 (4) | 0.029 (2) | 0.009 (3) | 0.006 (2) | 0.006 (2) |
C8B | 0.046 (3) | 0.084 (4) | 0.031 (2) | 0.011 (3) | 0.004 (2) | 0.002 (2) |
C9B | 0.067 (3) | 0.077 (4) | 0.043 (2) | 0.011 (3) | 0.017 (2) | 0.018 (2) |
C10B | 0.043 (3) | 0.110 (5) | 0.039 (3) | −0.005 (3) | −0.003 (2) | 0.003 (3) |
C11 | 0.091 (3) | 0.094 (3) | 0.0314 (14) | 0.018 (2) | 0.0045 (15) | −0.0018 (16) |
C12 | 0.076 (2) | 0.095 (3) | 0.0527 (19) | 0.025 (2) | 0.0108 (17) | 0.0064 (18) |
C13 | 0.0429 (14) | 0.0477 (15) | 0.0375 (13) | −0.0095 (12) | −0.0024 (11) | 0.0030 (12) |
C14 | 0.0464 (15) | 0.0569 (17) | 0.0358 (13) | −0.0101 (13) | 0.0046 (12) | 0.0033 (12) |
C15 | 0.0395 (14) | 0.0581 (17) | 0.0327 (12) | 0.0045 (12) | 0.0019 (10) | −0.0006 (12) |
C16 | 0.0687 (19) | 0.0571 (18) | 0.0351 (14) | 0.0133 (15) | 0.0062 (13) | 0.0002 (13) |
C17 | 0.084 (2) | 0.078 (2) | 0.0405 (16) | 0.0322 (19) | 0.0114 (16) | 0.0082 (16) |
C18 | 0.0558 (19) | 0.110 (3) | 0.0325 (14) | 0.0341 (19) | −0.0014 (13) | −0.0061 (17) |
C19 | 0.0449 (17) | 0.093 (3) | 0.0464 (17) | 0.0086 (16) | −0.0058 (13) | −0.0215 (17) |
C20 | 0.0428 (15) | 0.0642 (19) | 0.0480 (16) | 0.0009 (13) | −0.0038 (12) | −0.0113 (14) |
C21 | 0.0457 (15) | 0.0613 (18) | 0.0309 (12) | −0.0080 (13) | 0.0054 (11) | 0.0038 (12) |
C22 | 0.0475 (16) | 0.0636 (19) | 0.0446 (15) | −0.0091 (14) | 0.0088 (13) | −0.0012 (14) |
C23 | 0.0467 (17) | 0.067 (2) | 0.0522 (17) | −0.0117 (15) | 0.0071 (13) | −0.0011 (15) |
C24 | 0.0475 (16) | 0.0637 (19) | 0.0463 (16) | −0.0040 (14) | 0.0091 (13) | 0.0057 (14) |
C25 | 0.0561 (18) | 0.0593 (18) | 0.0416 (15) | −0.0071 (14) | 0.0094 (13) | 0.0009 (13) |
C26 | 0.0502 (16) | 0.0634 (19) | 0.0328 (13) | −0.0079 (14) | −0.0002 (12) | −0.0002 (13) |
C27 | 0.095 (3) | 0.151 (5) | 0.044 (2) | 0.061 (3) | −0.008 (2) | −0.002 (3) |
C28 | 0.057 (2) | 0.071 (2) | 0.076 (2) | −0.0062 (17) | 0.0109 (18) | −0.0050 (19) |
F1A | 0.070 (2) | 0.182 (4) | 0.0626 (17) | 0.032 (2) | −0.0320 (15) | 0.006 (2) |
F2A | 0.129 (3) | 0.245 (6) | 0.0508 (17) | −0.012 (4) | −0.0115 (19) | 0.061 (3) |
F3A | 0.248 (7) | 0.316 (8) | 0.0281 (14) | 0.199 (7) | −0.019 (3) | −0.035 (3) |
F4 | 0.0469 (12) | 0.0888 (16) | 0.154 (2) | −0.0029 (11) | 0.0057 (13) | −0.0078 (15) |
F5 | 0.0565 (14) | 0.0885 (19) | 0.300 (5) | 0.0078 (12) | 0.024 (2) | 0.077 (2) |
F6 | 0.140 (3) | 0.256 (5) | 0.113 (2) | 0.112 (3) | 0.004 (2) | −0.057 (3) |
B1 | 0.0457 (18) | 0.0520 (19) | 0.0471 (17) | −0.0114 (15) | −0.0071 (14) | 0.0157 (15) |
B2 | 0.0445 (17) | 0.068 (2) | 0.0343 (15) | −0.0084 (16) | 0.0066 (13) | 0.0014 (15) |
C1S | 0.174 (10) | 0.213 (12) | 0.089 (6) | −0.003 (10) | −0.020 (6) | −0.003 (7) |
C2S | 0.064 (6) | 0.251 (15) | 0.038 (4) | −0.001 (7) | 0.003 (4) | −0.008 (6) |
C3S | 0.092 (7) | 0.209 (14) | 0.072 (6) | −0.002 (9) | 0.006 (5) | 0.016 (8) |
Geometric parameters (Å, º) top
O1—C1B | 1.228 (6) | C9B—H9B1 | 0.9799 |
O1—B1 | 1.371 (4) | C9B—H9B2 | 0.9800 |
O1—C1A | 1.598 (6) | C9B—H9B3 | 0.9800 |
O2A—C2A | 1.471 (6) | C10B—H104 | 0.9800 |
O2A—B1 | 1.500 (5) | C10B—H105 | 0.9800 |
O3A—B2 | 1.358 (7) | C10B—H106 | 0.9799 |
O3A—C7A | 1.485 (12) | C11—H111 | 0.9801 |
O4A—B2 | 1.465 (7) | C11—H112 | 0.9799 |
O4A—C8A | 1.495 (11) | C11—H113 | 0.9800 |
O2B—B1 | 1.307 (5) | C11—H114 | 0.9801 |
O2B—C2B | 1.392 (6) | C11—H115 | 0.9799 |
O3B—B2 | 1.383 (4) | C11—H116 | 0.9800 |
O3B—C7B | 1.473 (6) | C12—H121 | 0.9802 |
O4B—B2 | 1.308 (5) | C12—H122 | 0.9799 |
O4B—C8B | 1.468 (6) | C12—H123 | 0.9800 |
C1A—C3A | 1.509 (8) | C12—H124 | 0.9800 |
C1A—C4A | 1.526 (9) | C12—H125 | 0.9798 |
C1A—C2A | 1.567 (7) | C12—H126 | 0.9801 |
C2A—C5A | 1.504 (8) | C13—C14 | 1.348 (4) |
C2A—C6A | 1.515 (8) | C13—C15 | 1.499 (3) |
C3A—H31A | 0.9800 | C13—B1 | 1.564 (5) |
C3A—H32A | 0.9800 | C14—C21 | 1.489 (4) |
C3A—H33A | 0.9801 | C14—B2 | 1.570 (4) |
C4A—H41A | 0.9799 | C15—C16 | 1.386 (4) |
C4A—H42A | 0.9800 | C15—C20 | 1.391 (4) |
C4A—H43A | 0.9800 | C16—C17 | 1.389 (4) |
C5A—H51A | 0.9800 | C16—H16 | 0.9500 |
C5A—H52A | 0.9801 | C17—C18 | 1.381 (5) |
C5A—H53A | 0.9801 | C17—H17 | 0.9501 |
C6A—H61A | 0.9800 | C18—C19 | 1.371 (6) |
C6A—H62A | 0.9799 | C18—C27 | 1.495 (5) |
C6A—H63A | 0.9800 | C19—C20 | 1.384 (4) |
C7A—C8A | 1.481 (18) | C19—H19 | 0.9500 |
C7A—C11 | 1.499 (14) | C20—H20 | 0.9500 |
C7A—C10A | 1.55 (2) | C21—C22 | 1.386 (4) |
C8A—C12 | 1.467 (12) | C21—C26 | 1.398 (4) |
C8A—C9A | 1.538 (19) | C22—C23 | 1.383 (4) |
C9A—H9A1 | 0.9800 | C22—H22 | 0.9500 |
C9A—H9A2 | 0.9800 | C23—C24 | 1.374 (5) |
C9A—H9A3 | 0.9799 | C23—H23 | 0.9500 |
C10A—H101 | 0.9802 | C24—C25 | 1.397 (4) |
C10A—H102 | 0.9800 | C24—C28 | 1.488 (5) |
C10A—H103 | 0.9800 | C25—C26 | 1.371 (4) |
C1B—C2B | 1.379 (7) | C25—H25 | 0.9500 |
C1B—C6B | 1.414 (9) | C26—H26 | 0.9500 |
C2B—C3B | 1.374 (8) | C27—F3B | 1.16 (2) |
C3B—C4B | 1.377 (9) | C27—F3A | 1.275 (6) |
C3B—H3B | 0.9500 | C27—F2B | 1.33 (2) |
C4B—C5B | 1.375 (9) | C27—F1A | 1.333 (6) |
C4B—H4B | 0.9500 | C27—F2A | 1.346 (8) |
C5B—C6B | 1.384 (10) | C27—F1B | 1.398 (16) |
C5B—H5B | 0.9500 | C28—F5 | 1.288 (5) |
C6B—H6B | 0.9501 | C28—F6 | 1.302 (5) |
C7B—C11 | 1.486 (6) | C28—F4 | 1.314 (4) |
C7B—C9B | 1.515 (8) | C1S—C3Si | 1.504 (17) |
C7B—C8B | 1.564 (8) | C1S—C3S | 1.504 (17) |
C8B—C10B | 1.506 (9) | C2S—C3S | 1.465 (18) |
C8B—C12 | 1.527 (7) | C2S—C2Sii | 1.56 (3) |
| | | |
C1B—O1—B1 | 107.2 (3) | C8B—C10B—H104 | 110.3 |
B1—O1—C1A | 108.7 (3) | C8B—C10B—H105 | 109.9 |
C2A—O2A—B1 | 110.6 (3) | H104—C10B—H105 | 109.5 |
B2—O3A—C7A | 105.9 (7) | C8B—C10B—H106 | 108.1 |
B2—O4A—C8A | 102.2 (6) | H104—C10B—H106 | 109.5 |
B1—O2B—C2B | 100.5 (3) | H105—C10B—H106 | 109.5 |
B2—O3B—C7B | 105.2 (3) | C7A—C11—H111 | 109.8 |
B2—O4B—C8B | 108.3 (3) | C7A—C11—H112 | 109.0 |
C3A—C1A—C4A | 113.7 (5) | H111—C11—H112 | 109.5 |
C3A—C1A—C2A | 114.0 (5) | C7A—C11—H113 | 109.6 |
C4A—C1A—C2A | 112.8 (5) | H111—C11—H113 | 109.5 |
C3A—C1A—O1 | 104.1 (4) | H112—C11—H113 | 109.5 |
C4A—C1A—O1 | 107.4 (5) | C7B—C11—H114 | 108.0 |
C2A—C1A—O1 | 103.5 (4) | C7B—C11—H115 | 108.6 |
O2A—C2A—C5A | 109.3 (4) | H114—C11—H115 | 109.5 |
O2A—C2A—C6A | 105.7 (4) | C7B—C11—H116 | 111.8 |
C5A—C2A—C6A | 111.7 (5) | H114—C11—H116 | 109.5 |
O2A—C2A—C1A | 101.5 (4) | H115—C11—H116 | 109.5 |
C5A—C2A—C1A | 114.3 (5) | C8A—C12—H121 | 109.3 |
C6A—C2A—C1A | 113.3 (5) | C8A—C12—H122 | 109.6 |
C1A—C3A—H31A | 109.7 | H121—C12—H122 | 109.5 |
C1A—C3A—H32A | 108.9 | C8A—C12—H123 | 109.5 |
H31A—C3A—H32A | 109.5 | H121—C12—H123 | 109.5 |
C1A—C3A—H33A | 109.9 | H122—C12—H123 | 109.5 |
H31A—C3A—H33A | 109.4 | C8B—C12—H124 | 109.9 |
H32A—C3A—H33A | 109.5 | C8B—C12—H125 | 107.7 |
C1A—C4A—H41A | 109.7 | H124—C12—H125 | 109.5 |
C1A—C4A—H42A | 109.9 | C8B—C12—H126 | 110.8 |
H41A—C4A—H42A | 109.5 | H124—C12—H126 | 109.5 |
C1A—C4A—H43A | 108.7 | H125—C12—H126 | 109.5 |
H41A—C4A—H43A | 109.5 | C14—C13—C15 | 122.2 (3) |
H42A—C4A—H43A | 109.5 | C14—C13—B1 | 124.0 (2) |
C2A—C5A—H51A | 109.5 | C15—C13—B1 | 113.6 (2) |
C2A—C5A—H52A | 109.0 | C13—C14—C21 | 122.5 (2) |
H51A—C5A—H52A | 109.5 | C13—C14—B2 | 117.5 (3) |
C2A—C5A—H53A | 109.9 | C21—C14—B2 | 119.9 (2) |
H51A—C5A—H53A | 109.5 | C16—C15—C20 | 119.7 (3) |
H52A—C5A—H53A | 109.5 | C16—C15—C13 | 120.0 (2) |
C2A—C6A—H61A | 109.5 | C20—C15—C13 | 120.3 (3) |
C2A—C6A—H62A | 109.3 | C15—C16—C17 | 119.6 (3) |
H61A—C6A—H62A | 109.5 | C15—C16—H16 | 120.3 |
C2A—C6A—H63A | 109.7 | C17—C16—H16 | 120.0 |
H61A—C6A—H63A | 109.5 | C18—C17—C16 | 120.0 (3) |
H62A—C6A—H63A | 109.5 | C18—C17—H17 | 120.1 |
C8A—C7A—O3A | 105.0 (8) | C16—C17—H17 | 119.8 |
C8A—C7A—C11 | 120.8 (11) | C19—C18—C17 | 120.6 (3) |
O3A—C7A—C11 | 107.1 (9) | C19—C18—C27 | 119.3 (4) |
C8A—C7A—C10A | 113.1 (13) | C17—C18—C27 | 120.2 (4) |
O3A—C7A—C10A | 103.0 (11) | C18—C19—C20 | 119.8 (3) |
C11—C7A—C10A | 106.3 (9) | C18—C19—H19 | 120.3 |
C12—C8A—C7A | 117.4 (10) | C20—C19—H19 | 119.9 |
C12—C8A—O4A | 105.2 (8) | C19—C20—C15 | 120.2 (3) |
C7A—C8A—O4A | 104.6 (8) | C19—C20—H20 | 119.6 |
C12—C8A—C9A | 107.9 (9) | C15—C20—H20 | 120.2 |
C7A—C8A—C9A | 114.2 (12) | C22—C21—C26 | 118.4 (3) |
O4A—C8A—C9A | 106.5 (9) | C22—C21—C14 | 120.5 (3) |
C8A—C9A—H9A1 | 107.8 | C26—C21—C14 | 121.1 (2) |
C8A—C9A—H9A2 | 110.9 | C23—C22—C21 | 120.7 (3) |
H9A1—C9A—H9A2 | 109.5 | C23—C22—H22 | 119.9 |
C8A—C9A—H9A3 | 109.7 | C21—C22—H22 | 119.3 |
H9A1—C9A—H9A3 | 109.5 | C24—C23—C22 | 120.5 (3) |
H9A2—C9A—H9A3 | 109.5 | C24—C23—H23 | 119.7 |
C7A—C10A—H101 | 106.5 | C22—C23—H23 | 119.8 |
C7A—C10A—H102 | 110.8 | C23—C24—C25 | 119.3 (3) |
H101—C10A—H102 | 109.5 | C23—C24—C28 | 120.8 (3) |
C7A—C10A—H103 | 111.1 | C25—C24—C28 | 119.9 (3) |
H101—C10A—H103 | 109.5 | C26—C25—C24 | 120.1 (3) |
H102—C10A—H103 | 109.5 | C26—C25—H25 | 120.1 |
O1—C1B—C2B | 108.6 (5) | C24—C25—H25 | 119.8 |
O1—C1B—C6B | 128.1 (5) | C25—C26—C21 | 120.9 (3) |
C2B—C1B—C6B | 123.3 (6) | C25—C26—H26 | 119.6 |
C3B—C2B—C1B | 121.4 (5) | C21—C26—H26 | 119.5 |
C3B—C2B—O2B | 128.9 (5) | F3B—C27—F2B | 106.1 (16) |
C1B—C2B—O2B | 109.6 (4) | F3A—C27—F1A | 106.4 (6) |
C2B—C3B—C4B | 116.6 (6) | F3A—C27—F2A | 111.7 (6) |
H61A—C3B—H63A | 98.3 | F1A—C27—F2A | 99.4 (4) |
C2B—C3B—H3B | 121.2 | F3B—C27—F1B | 104.0 (16) |
C4B—C3B—H3B | 122.2 | F2B—C27—F1B | 96.3 (10) |
C5B—C4B—C3B | 121.7 (6) | F3B—C27—C18 | 122.8 (12) |
C5B—C4B—H4B | 119.2 | F3A—C27—C18 | 113.5 (4) |
C3B—C4B—H4B | 119.1 | F2B—C27—C18 | 116.1 (10) |
C4B—C5B—C6B | 123.9 (7) | F1A—C27—C18 | 111.4 (4) |
C4B—C5B—H5B | 117.6 | F2A—C27—C18 | 113.4 (5) |
C6B—C5B—H5B | 118.4 | F1B—C27—C18 | 107.7 (7) |
C5B—C6B—C1B | 113.0 (6) | F5—C28—F6 | 106.1 (4) |
C5B—C6B—H6B | 123.9 | F5—C28—F4 | 104.3 (3) |
C1B—C6B—H6B | 123.1 | F6—C28—F4 | 104.3 (4) |
O3B—C7B—C11 | 109.2 (4) | F5—C28—C24 | 114.0 (3) |
O3B—C7B—C9B | 106.0 (4) | F6—C28—C24 | 112.7 (3) |
C11—C7B—C9B | 110.7 (4) | F4—C28—C24 | 114.5 (3) |
O3B—C7B—C8B | 101.8 (4) | O2B—B1—O1 | 113.7 (3) |
C11—C7B—C8B | 115.7 (5) | O1—B1—O2A | 108.2 (3) |
C9B—C7B—C8B | 112.6 (5) | O2B—B1—C13 | 122.9 (3) |
O4B—C8B—C10B | 105.7 (4) | O1—B1—C13 | 122.6 (3) |
O4B—C8B—C12 | 110.0 (4) | O2A—B1—C13 | 124.7 (3) |
C10B—C8B—C12 | 111.0 (4) | O1—B1—C2B | 72.6 (2) |
O4B—C8B—C7B | 100.6 (4) | O4B—B2—O3A | 106.3 (4) |
C10B—C8B—C7B | 113.7 (6) | O4B—B2—O3B | 114.4 (3) |
C12—C8B—C7B | 115.0 (5) | O3A—B2—O4A | 113.5 (4) |
C7B—C9B—H9B1 | 109.4 | O4B—B2—C14 | 121.3 (3) |
H9A3—C9B—H9B1 | 100.2 | O3A—B2—C14 | 125.9 (4) |
C7B—C9B—H9B2 | 109.9 | O3B—B2—C14 | 124.3 (3) |
H9B1—C9B—H9B2 | 109.5 | O4A—B2—C14 | 120.5 (3) |
C7B—C9B—H9B3 | 109.1 | C3Si—C1S—C3S | 179.997 (5) |
H9B1—C9B—H9B3 | 109.5 | C3S—C2S—C2Sii | 116.0 (11) |
H9B2—C9B—H9B3 | 109.5 | C2S—C3S—C1S | 118.2 (9) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1. |
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