Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961700105X/sk3650sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961700105X/sk3650Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961700105X/sk3650IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961700105X/sk3650IIIsup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961700105X/sk3650Isup5.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961700105X/sk3650IIsup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961700105X/sk3650IIIsup7.cml |
CCDC references: 1528834; 1528833; 1528832
For all compounds, data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT-Plus (Bruker, 2012); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).
C19H13FO | Z = 4 |
Mr = 276.29 | F(000) = 576 |
Triclinic, P1 | Dx = 1.336 Mg m−3 |
a = 7.6678 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.5007 (5) Å | Cell parameters from 6071 reflections |
c = 15.7874 (8) Å | θ = 1.3–27.2° |
α = 96.249 (3)° | µ = 0.09 mm−1 |
β = 96.752 (3)° | T = 296 K |
γ = 90.796 (3)° | Block, colourless |
V = 1373.84 (12) Å3 | 0.41 × 0.32 × 0.30 mm |
Bruker Kappa APEXII diffractometer | 3046 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.032 |
φ and ω scans | θmax = 26.6°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −9→9 |
Tmin = 0.960, Tmax = 0.973 | k = −14→14 |
25027 measured reflections | l = −19→19 |
5721 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.182 | w = 1/[σ2(Fo2) + (0.0648P)2 + 0.5614P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
5721 reflections | Δρmax = 0.21 e Å−3 |
379 parameters | Δρmin = −0.19 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C11 | 0.2636 (3) | 0.49245 (19) | 0.46846 (15) | 0.0455 (6) | |
O11 | 0.2606 (3) | 0.59900 (14) | 0.46856 (12) | 0.0680 (6) | |
C12 | 0.2197 (3) | 0.4364 (2) | 0.54308 (16) | 0.0538 (7) | |
H12 | 0.1913 | 0.3568 | 0.5362 | 0.065* | |
C13 | 0.2193 (3) | 0.49594 (19) | 0.61931 (16) | 0.0458 (6) | |
H13 | 0.2513 | 0.5749 | 0.6237 | 0.055* | |
C111 | 0.2880 (3) | 0.45775 (18) | 0.31358 (15) | 0.0407 (5) | |
H111 | 0.2416 | 0.5313 | 0.3088 | 0.049* | |
C112 | 0.3106 (3) | 0.41720 (18) | 0.39246 (15) | 0.0421 (5) | |
C113 | 0.3852 (3) | 0.30607 (19) | 0.39978 (16) | 0.0473 (6) | |
H113 | 0.4006 | 0.2773 | 0.4529 | 0.057* | |
C114 | 0.4342 (3) | 0.24143 (19) | 0.32976 (17) | 0.0488 (6) | |
H114 | 0.4852 | 0.1695 | 0.3361 | 0.059* | |
C115 | 0.4574 (3) | 0.2146 (2) | 0.17426 (18) | 0.0532 (6) | |
H115 | 0.5056 | 0.1414 | 0.1788 | 0.064* | |
C116 | 0.4343 (4) | 0.2558 (2) | 0.09649 (19) | 0.0648 (8) | |
H116 | 0.4684 | 0.2113 | 0.0487 | 0.078* | |
C117 | 0.3594 (4) | 0.3650 (2) | 0.08786 (18) | 0.0643 (7) | |
H117 | 0.3434 | 0.3926 | 0.0343 | 0.077* | |
C118 | 0.3100 (3) | 0.4308 (2) | 0.15763 (16) | 0.0530 (6) | |
H118 | 0.2602 | 0.5031 | 0.1512 | 0.064* | |
C119 | 0.3332 (3) | 0.39099 (18) | 0.23947 (15) | 0.0397 (5) | |
C120 | 0.4100 (3) | 0.28039 (18) | 0.24811 (15) | 0.0425 (6) | |
C131 | 0.1745 (3) | 0.45205 (18) | 0.69754 (15) | 0.0425 (6) | |
C132 | 0.2077 (3) | 0.5214 (2) | 0.77522 (16) | 0.0508 (6) | |
H132 | 0.2608 | 0.5949 | 0.7768 | 0.061* | |
C133 | 0.1641 (4) | 0.4845 (2) | 0.85047 (17) | 0.0594 (7) | |
H133 | 0.1883 | 0.5316 | 0.9024 | 0.071* | |
C134 | 0.0843 (4) | 0.3767 (2) | 0.84632 (18) | 0.0589 (7) | |
F134 | 0.0381 (3) | 0.34032 (16) | 0.91995 (11) | 0.0930 (6) | |
C135 | 0.0490 (3) | 0.3046 (2) | 0.77151 (17) | 0.0536 (6) | |
H135 | −0.0044 | 0.2313 | 0.7708 | 0.064* | |
C136 | 0.0938 (3) | 0.3424 (2) | 0.69728 (17) | 0.0488 (6) | |
H136 | 0.0701 | 0.2941 | 0.6459 | 0.059* | |
C21 | 0.2219 (3) | 1.00381 (19) | 0.54713 (15) | 0.0453 (6) | |
O21 | 0.2219 (3) | 1.10970 (14) | 0.54542 (11) | 0.0664 (5) | |
C22 | 0.2670 (3) | 0.9241 (2) | 0.47339 (15) | 0.0508 (6) | |
H22 | 0.2901 | 0.8464 | 0.4804 | 0.061* | |
C23 | 0.2750 (3) | 0.96147 (19) | 0.39753 (15) | 0.0455 (6) | |
H23 | 0.2476 | 1.0393 | 0.3932 | 0.055* | |
C211 | 0.2104 (3) | 1.01657 (17) | 0.70294 (14) | 0.0398 (5) | |
H211 | 0.2589 | 1.0918 | 0.7067 | 0.048* | |
C212 | 0.1777 (3) | 0.95200 (18) | 0.62421 (15) | 0.0413 (5) | |
C213 | 0.1001 (3) | 0.83855 (19) | 0.61895 (16) | 0.0470 (6) | |
H213 | 0.0788 | 0.7937 | 0.5659 | 0.056* | |
C214 | 0.0566 (3) | 0.79453 (19) | 0.69011 (16) | 0.0471 (6) | |
H214 | 0.0022 | 0.7209 | 0.6849 | 0.057* | |
C215 | 0.0533 (3) | 0.8133 (2) | 0.84710 (17) | 0.0533 (7) | |
H215 | −0.0028 | 0.7404 | 0.8432 | 0.064* | |
C216 | 0.0963 (4) | 0.8748 (2) | 0.92514 (18) | 0.0639 (7) | |
H216 | 0.0723 | 0.8430 | 0.9744 | 0.077* | |
C217 | 0.1770 (4) | 0.9862 (2) | 0.93198 (17) | 0.0619 (7) | |
H217 | 0.2065 | 1.0280 | 0.9857 | 0.074* | |
C218 | 0.2122 (3) | 1.0334 (2) | 0.86059 (16) | 0.0508 (6) | |
H218 | 0.2636 | 1.1079 | 0.8659 | 0.061* | |
C219 | 0.1722 (3) | 0.97130 (18) | 0.77841 (14) | 0.0391 (5) | |
C220 | 0.0922 (3) | 0.85821 (18) | 0.77167 (15) | 0.0406 (5) | |
C231 | 0.3216 (3) | 0.89484 (18) | 0.32013 (14) | 0.0407 (5) | |
C232 | 0.2893 (3) | 0.9409 (2) | 0.24220 (16) | 0.0497 (6) | |
H232 | 0.2392 | 1.0139 | 0.2407 | 0.060* | |
C233 | 0.3301 (3) | 0.8805 (2) | 0.16714 (17) | 0.0578 (7) | |
H233 | 0.3064 | 0.9113 | 0.1150 | 0.069* | |
C234 | 0.4060 (4) | 0.7744 (2) | 0.17121 (17) | 0.0576 (7) | |
F234 | 0.4474 (3) | 0.71518 (15) | 0.09738 (11) | 0.0926 (6) | |
C235 | 0.4438 (3) | 0.7263 (2) | 0.24616 (16) | 0.0500 (6) | |
H235 | 0.4976 | 0.6544 | 0.2469 | 0.060* | |
C236 | 0.4009 (3) | 0.78637 (19) | 0.32071 (16) | 0.0466 (6) | |
H236 | 0.4250 | 0.7542 | 0.3723 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0406 (14) | 0.0416 (13) | 0.0530 (15) | −0.0046 (10) | −0.0008 (11) | 0.0067 (11) |
O11 | 0.0959 (15) | 0.0433 (10) | 0.0657 (12) | −0.0017 (9) | 0.0145 (10) | 0.0047 (8) |
C12 | 0.0609 (17) | 0.0413 (13) | 0.0590 (17) | −0.0063 (11) | 0.0085 (13) | 0.0034 (12) |
C13 | 0.0413 (14) | 0.0379 (12) | 0.0581 (16) | 0.0012 (10) | 0.0048 (11) | 0.0066 (11) |
C111 | 0.0335 (12) | 0.0328 (11) | 0.0558 (15) | 0.0008 (9) | 0.0003 (10) | 0.0104 (10) |
C112 | 0.0386 (13) | 0.0355 (11) | 0.0513 (15) | −0.0050 (10) | 0.0021 (11) | 0.0053 (10) |
C113 | 0.0405 (14) | 0.0455 (13) | 0.0557 (15) | −0.0025 (11) | −0.0029 (11) | 0.0145 (11) |
C114 | 0.0389 (14) | 0.0366 (12) | 0.0710 (18) | 0.0057 (10) | 0.0021 (12) | 0.0104 (12) |
C115 | 0.0421 (14) | 0.0449 (13) | 0.0724 (19) | 0.0025 (11) | 0.0119 (13) | 0.0004 (13) |
C116 | 0.0635 (19) | 0.0711 (18) | 0.0595 (19) | −0.0033 (15) | 0.0158 (14) | −0.0033 (15) |
C117 | 0.0679 (19) | 0.0714 (18) | 0.0541 (17) | −0.0033 (15) | 0.0041 (14) | 0.0133 (14) |
C118 | 0.0516 (16) | 0.0502 (14) | 0.0574 (17) | 0.0018 (12) | 0.0006 (13) | 0.0126 (12) |
C119 | 0.0297 (12) | 0.0379 (11) | 0.0510 (14) | −0.0041 (9) | 0.0013 (10) | 0.0069 (10) |
C120 | 0.0305 (12) | 0.0387 (12) | 0.0581 (16) | −0.0024 (9) | 0.0029 (11) | 0.0065 (11) |
C131 | 0.0348 (13) | 0.0371 (11) | 0.0553 (15) | 0.0043 (10) | 0.0028 (11) | 0.0056 (11) |
C132 | 0.0472 (15) | 0.0426 (13) | 0.0625 (17) | 0.0002 (11) | 0.0069 (12) | 0.0053 (12) |
C133 | 0.0583 (17) | 0.0612 (16) | 0.0557 (17) | −0.0013 (13) | 0.0004 (13) | 0.0008 (13) |
C134 | 0.0538 (17) | 0.0670 (17) | 0.0590 (18) | 0.0017 (13) | 0.0061 (13) | 0.0217 (14) |
F134 | 0.1102 (15) | 0.1042 (13) | 0.0695 (12) | −0.0169 (11) | 0.0150 (10) | 0.0292 (10) |
C135 | 0.0449 (15) | 0.0462 (13) | 0.0703 (19) | −0.0034 (11) | 0.0042 (13) | 0.0128 (13) |
C136 | 0.0424 (14) | 0.0442 (12) | 0.0592 (16) | 0.0009 (11) | 0.0046 (12) | 0.0053 (11) |
C21 | 0.0457 (14) | 0.0402 (12) | 0.0480 (15) | 0.0016 (10) | −0.0018 (11) | 0.0038 (11) |
O21 | 0.0979 (16) | 0.0444 (10) | 0.0589 (12) | 0.0038 (9) | 0.0149 (10) | 0.0084 (8) |
C22 | 0.0614 (17) | 0.0417 (13) | 0.0499 (15) | 0.0062 (11) | 0.0045 (12) | 0.0096 (11) |
C23 | 0.0435 (14) | 0.0382 (12) | 0.0553 (16) | 0.0015 (10) | 0.0063 (11) | 0.0066 (11) |
C211 | 0.0363 (12) | 0.0297 (10) | 0.0533 (15) | 0.0004 (9) | 0.0065 (10) | 0.0030 (10) |
C212 | 0.0388 (13) | 0.0346 (11) | 0.0501 (15) | 0.0049 (9) | 0.0030 (11) | 0.0054 (10) |
C213 | 0.0427 (14) | 0.0411 (12) | 0.0535 (15) | 0.0038 (10) | −0.0037 (11) | −0.0011 (11) |
C214 | 0.0413 (14) | 0.0353 (11) | 0.0640 (17) | −0.0023 (10) | 0.0022 (12) | 0.0070 (11) |
C215 | 0.0467 (15) | 0.0468 (13) | 0.0702 (19) | −0.0008 (11) | 0.0149 (13) | 0.0156 (13) |
C216 | 0.0690 (19) | 0.0683 (17) | 0.0595 (18) | 0.0029 (15) | 0.0199 (15) | 0.0162 (14) |
C217 | 0.0699 (19) | 0.0642 (17) | 0.0516 (17) | 0.0005 (14) | 0.0126 (14) | 0.0015 (13) |
C218 | 0.0526 (15) | 0.0428 (13) | 0.0567 (16) | 0.0008 (11) | 0.0100 (12) | 0.0004 (11) |
C219 | 0.0329 (12) | 0.0373 (11) | 0.0476 (14) | 0.0059 (9) | 0.0066 (10) | 0.0038 (10) |
C220 | 0.0296 (12) | 0.0363 (11) | 0.0559 (15) | 0.0025 (9) | 0.0031 (10) | 0.0069 (10) |
C231 | 0.0369 (13) | 0.0377 (11) | 0.0480 (14) | −0.0023 (10) | 0.0037 (10) | 0.0083 (10) |
C232 | 0.0457 (15) | 0.0450 (13) | 0.0607 (17) | 0.0005 (11) | 0.0063 (12) | 0.0167 (12) |
C233 | 0.0624 (18) | 0.0638 (16) | 0.0497 (16) | −0.0073 (14) | 0.0067 (13) | 0.0189 (13) |
C234 | 0.0617 (18) | 0.0574 (16) | 0.0555 (17) | −0.0070 (13) | 0.0192 (14) | 0.0020 (13) |
F234 | 0.1272 (16) | 0.0911 (12) | 0.0633 (11) | 0.0034 (11) | 0.0390 (11) | −0.0037 (9) |
C235 | 0.0463 (15) | 0.0433 (13) | 0.0622 (17) | 0.0019 (11) | 0.0129 (12) | 0.0065 (12) |
C236 | 0.0459 (14) | 0.0461 (13) | 0.0486 (15) | −0.0011 (11) | 0.0052 (11) | 0.0098 (11) |
C11—O11 | 1.226 (3) | C21—O21 | 1.221 (2) |
C11—C12 | 1.473 (3) | C21—C22 | 1.478 (3) |
C11—C112 | 1.484 (3) | C21—C212 | 1.483 (3) |
C12—C13 | 1.318 (3) | C22—C23 | 1.323 (3) |
C12—H12 | 0.9300 | C22—H22 | 0.9300 |
C13—C131 | 1.459 (3) | C23—C231 | 1.454 (3) |
C13—H13 | 0.9300 | C23—H23 | 0.9300 |
C111—C112 | 1.370 (3) | C211—C212 | 1.371 (3) |
C111—C119 | 1.409 (3) | C211—C219 | 1.411 (3) |
C111—H111 | 0.9300 | C211—H211 | 0.9300 |
C112—C113 | 1.418 (3) | C212—C213 | 1.416 (3) |
C113—C114 | 1.357 (3) | C213—C214 | 1.355 (3) |
C113—H113 | 0.9300 | C213—H213 | 0.9300 |
C114—C120 | 1.403 (3) | C214—C220 | 1.406 (3) |
C114—H114 | 0.9300 | C214—H214 | 0.9300 |
C115—C116 | 1.357 (4) | C215—C216 | 1.354 (3) |
C115—C120 | 1.407 (3) | C215—C220 | 1.409 (3) |
C115—H115 | 0.9300 | C215—H215 | 0.9300 |
C116—C117 | 1.402 (4) | C216—C217 | 1.403 (4) |
C116—H116 | 0.9300 | C216—H216 | 0.9300 |
C117—C118 | 1.362 (3) | C217—C218 | 1.355 (3) |
C117—H117 | 0.9300 | C217—H217 | 0.9300 |
C118—C119 | 1.410 (3) | C218—C219 | 1.409 (3) |
C118—H118 | 0.9300 | C218—H218 | 0.9300 |
C119—C120 | 1.422 (3) | C219—C220 | 1.418 (3) |
C131—C132 | 1.383 (3) | C231—C232 | 1.389 (3) |
C131—C136 | 1.396 (3) | C231—C236 | 1.396 (3) |
C132—C133 | 1.379 (3) | C232—C233 | 1.378 (3) |
C132—H132 | 0.9300 | C232—H232 | 0.9300 |
C133—C134 | 1.368 (4) | C233—C234 | 1.364 (4) |
C133—H133 | 0.9300 | C233—H233 | 0.9300 |
C134—F134 | 1.360 (3) | C234—F234 | 1.358 (3) |
C134—C135 | 1.364 (4) | C234—C235 | 1.363 (3) |
C135—C136 | 1.372 (3) | C235—C236 | 1.375 (3) |
C135—H135 | 0.9300 | C235—H235 | 0.9300 |
C136—H136 | 0.9300 | C236—H236 | 0.9300 |
O11—C11—C12 | 120.9 (2) | O21—C21—C22 | 121.3 (2) |
O11—C11—C112 | 120.4 (2) | O21—C21—C212 | 120.4 (2) |
C12—C11—C112 | 118.7 (2) | C22—C21—C212 | 118.30 (19) |
C13—C12—C11 | 121.9 (2) | C23—C22—C21 | 121.2 (2) |
C13—C12—H12 | 119.1 | C23—C22—H22 | 119.4 |
C11—C12—H12 | 119.1 | C21—C22—H22 | 119.4 |
C12—C13—C131 | 127.4 (2) | C22—C23—C231 | 127.5 (2) |
C12—C13—H13 | 116.3 | C22—C23—H23 | 116.3 |
C131—C13—H13 | 116.3 | C231—C23—H23 | 116.3 |
C112—C111—C119 | 121.8 (2) | C212—C211—C219 | 121.39 (19) |
C112—C111—H111 | 119.1 | C212—C211—H211 | 119.3 |
C119—C111—H111 | 119.1 | C219—C211—H211 | 119.3 |
C111—C112—C113 | 118.9 (2) | C211—C212—C213 | 118.9 (2) |
C111—C112—C11 | 119.3 (2) | C211—C212—C21 | 119.02 (19) |
C113—C112—C11 | 121.7 (2) | C213—C212—C21 | 122.1 (2) |
C114—C113—C112 | 120.4 (2) | C214—C213—C212 | 120.9 (2) |
C114—C113—H113 | 119.8 | C214—C213—H213 | 119.6 |
C112—C113—H113 | 119.8 | C212—C213—H213 | 119.6 |
C113—C114—C120 | 121.7 (2) | C213—C214—C220 | 121.2 (2) |
C113—C114—H114 | 119.2 | C213—C214—H214 | 119.4 |
C120—C114—H114 | 119.2 | C220—C214—H214 | 119.4 |
C116—C115—C120 | 121.3 (2) | C216—C215—C220 | 121.0 (2) |
C116—C115—H115 | 119.4 | C216—C215—H215 | 119.5 |
C120—C115—H115 | 119.4 | C220—C215—H215 | 119.5 |
C115—C116—C117 | 120.3 (3) | C215—C216—C217 | 120.2 (2) |
C115—C116—H116 | 119.8 | C215—C216—H216 | 119.9 |
C117—C116—H116 | 119.8 | C217—C216—H216 | 119.9 |
C118—C117—C116 | 120.2 (3) | C218—C217—C216 | 120.3 (2) |
C118—C117—H117 | 119.9 | C218—C217—H217 | 119.8 |
C116—C117—H117 | 119.9 | C216—C217—H217 | 119.8 |
C117—C118—C119 | 120.9 (2) | C217—C218—C219 | 121.1 (2) |
C117—C118—H118 | 119.5 | C217—C218—H218 | 119.4 |
C119—C118—H118 | 119.5 | C219—C218—H218 | 119.4 |
C111—C119—C118 | 122.7 (2) | C218—C219—C211 | 122.6 (2) |
C111—C119—C120 | 118.6 (2) | C218—C219—C220 | 118.5 (2) |
C118—C119—C120 | 118.7 (2) | C211—C219—C220 | 118.9 (2) |
C114—C120—C115 | 122.9 (2) | C214—C220—C215 | 122.5 (2) |
C114—C120—C119 | 118.6 (2) | C214—C220—C219 | 118.8 (2) |
C115—C120—C119 | 118.5 (2) | C215—C220—C219 | 118.8 (2) |
C132—C131—C136 | 117.8 (2) | C232—C231—C236 | 118.0 (2) |
C132—C131—C13 | 119.8 (2) | C232—C231—C23 | 119.3 (2) |
C136—C131—C13 | 122.4 (2) | C236—C231—C23 | 122.7 (2) |
C133—C132—C131 | 121.8 (2) | C233—C232—C231 | 121.3 (2) |
C133—C132—H132 | 119.1 | C233—C232—H232 | 119.4 |
C131—C132—H132 | 119.1 | C231—C232—H232 | 119.4 |
C134—C133—C132 | 118.0 (2) | C234—C233—C232 | 118.3 (2) |
C134—C133—H133 | 121.0 | C234—C233—H233 | 120.9 |
C132—C133—H133 | 121.0 | C232—C233—H233 | 120.9 |
F134—C134—C135 | 118.9 (2) | F234—C234—C235 | 118.8 (2) |
F134—C134—C133 | 118.4 (3) | F234—C234—C233 | 118.3 (2) |
C135—C134—C133 | 122.7 (3) | C235—C234—C233 | 122.8 (2) |
C134—C135—C136 | 118.6 (2) | C234—C235—C236 | 118.6 (2) |
C134—C135—H135 | 120.7 | C234—C235—H235 | 120.7 |
C136—C135—H135 | 120.7 | C236—C235—H235 | 120.7 |
C135—C136—C131 | 121.2 (2) | C235—C236—C231 | 121.0 (2) |
C135—C136—H136 | 119.4 | C235—C236—H236 | 119.5 |
C131—C136—H136 | 119.4 | C231—C236—H236 | 119.5 |
O11—C11—C12—C13 | −17.5 (4) | O21—C21—C22—C23 | −13.5 (4) |
C112—C11—C12—C13 | 162.9 (2) | C212—C21—C22—C23 | 167.1 (2) |
C11—C12—C13—C131 | 178.4 (2) | C21—C22—C23—C231 | 178.3 (2) |
C119—C111—C112—C113 | 1.4 (3) | C219—C211—C212—C213 | 1.4 (3) |
C119—C111—C112—C11 | 178.89 (19) | C219—C211—C212—C21 | −179.5 (2) |
O11—C11—C112—C111 | −23.9 (3) | O21—C21—C212—C211 | −27.9 (3) |
C12—C11—C112—C111 | 155.7 (2) | C22—C21—C212—C211 | 151.6 (2) |
O11—C11—C112—C113 | 153.6 (2) | O21—C21—C212—C213 | 151.1 (2) |
C12—C11—C112—C113 | −26.8 (3) | C22—C21—C212—C213 | −29.4 (3) |
C111—C112—C113—C114 | 0.4 (3) | C211—C212—C213—C214 | 0.8 (3) |
C11—C112—C113—C114 | −177.0 (2) | C21—C212—C213—C214 | −178.2 (2) |
C112—C113—C114—C120 | −1.4 (3) | C212—C213—C214—C220 | −2.1 (3) |
C120—C115—C116—C117 | −1.0 (4) | C220—C215—C216—C217 | 1.6 (4) |
C115—C116—C117—C118 | 0.3 (4) | C215—C216—C217—C218 | 0.1 (4) |
C116—C117—C118—C119 | 0.1 (4) | C216—C217—C218—C219 | −1.2 (4) |
C112—C111—C119—C118 | 179.6 (2) | C217—C218—C219—C211 | −178.6 (2) |
C112—C111—C119—C120 | −2.2 (3) | C217—C218—C219—C220 | 0.6 (3) |
C117—C118—C119—C111 | 178.3 (2) | C212—C211—C219—C218 | 176.8 (2) |
C117—C118—C119—C120 | 0.2 (3) | C212—C211—C219—C220 | −2.3 (3) |
C113—C114—C120—C115 | −179.1 (2) | C213—C214—C220—C215 | −178.1 (2) |
C113—C114—C120—C119 | 0.5 (3) | C213—C214—C220—C219 | 1.2 (3) |
C116—C115—C120—C114 | −179.1 (2) | C216—C215—C220—C214 | 177.0 (2) |
C116—C115—C120—C119 | 1.3 (3) | C216—C215—C220—C219 | −2.2 (3) |
C111—C119—C120—C114 | 1.2 (3) | C218—C219—C220—C214 | −178.2 (2) |
C118—C119—C120—C114 | 179.5 (2) | C211—C219—C220—C214 | 1.0 (3) |
C111—C119—C120—C115 | −179.1 (2) | C218—C219—C220—C215 | 1.1 (3) |
C118—C119—C120—C115 | −0.8 (3) | C211—C219—C220—C215 | −179.7 (2) |
C12—C13—C131—C132 | 169.7 (2) | C22—C23—C231—C232 | 167.2 (2) |
C12—C13—C131—C136 | −12.1 (4) | C22—C23—C231—C236 | −13.9 (4) |
C136—C131—C132—C133 | 0.3 (4) | C236—C231—C232—C233 | 1.5 (3) |
C13—C131—C132—C133 | 178.6 (2) | C23—C231—C232—C233 | −179.5 (2) |
C131—C132—C133—C134 | −0.8 (4) | C231—C232—C233—C234 | −1.0 (4) |
C132—C133—C134—F134 | −178.9 (2) | C232—C233—C234—F234 | −179.5 (2) |
C132—C133—C134—C135 | 0.9 (4) | C232—C233—C234—C235 | −0.4 (4) |
F134—C134—C135—C136 | 179.2 (2) | F234—C234—C235—C236 | −179.7 (2) |
C133—C134—C135—C136 | −0.7 (4) | C233—C234—C235—C236 | 1.2 (4) |
C134—C135—C136—C131 | 0.2 (4) | C234—C235—C236—C231 | −0.6 (4) |
C132—C131—C136—C135 | 0.0 (3) | C232—C231—C236—C235 | −0.7 (3) |
C13—C131—C136—C135 | −178.3 (2) | C23—C231—C236—C235 | −179.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C132—H132···Cg1i | 0.93 | 2.88 | 3.557 (3) | 131 |
C135—H135···Cg2ii | 0.93 | 2.83 | 3.503 (3) | 130 |
C214—H214···Cg3ii | 0.93 | 2.87 | 3.554 (2) | 131 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1. |
C19H13BrO | Z = 2 |
Mr = 337.19 | F(000) = 340 |
Triclinic, P1 | Dx = 1.563 Mg m−3 |
a = 5.8714 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.8616 (7) Å | Cell parameters from 3816 reflections |
c = 15.5954 (13) Å | θ = 1.3–29.8° |
α = 95.007 (5)° | µ = 2.86 mm−1 |
β = 90.218 (5)° | T = 296 K |
γ = 92.179 (5)° | Block, colourless |
V = 716.58 (11) Å3 | 0.30 × 0.28 × 0.27 mm |
Bruker Kappa APEXII diffractometer | 1842 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.054 |
φ and ω scans | θmax = 26.6°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −7→7 |
Tmin = 0.451, Tmax = 0.462 | k = −9→9 |
12745 measured reflections | l = −19→19 |
2941 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.082 | w = 1/[σ2(Fo2) + (0.0164P)2 + 0.6492P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
2941 reflections | Δρmax = 0.44 e Å−3 |
190 parameters | Δρmin = −0.47 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.5068 (6) | 0.2375 (4) | 0.4774 (2) | 0.0415 (9) | |
O1 | 0.7111 (4) | 0.2606 (3) | 0.49106 (15) | 0.0566 (7) | |
C2 | 0.3387 (6) | 0.3049 (5) | 0.5402 (2) | 0.0460 (9) | |
H2 | 0.1897 | 0.3177 | 0.5220 | 0.055* | |
C3 | 0.3935 (6) | 0.3475 (4) | 0.6212 (2) | 0.0407 (9) | |
H3 | 0.5422 | 0.3268 | 0.6369 | 0.049* | |
C11 | 0.5650 (5) | 0.1296 (4) | 0.3265 (2) | 0.0341 (8) | |
H11 | 0.7103 | 0.1809 | 0.3314 | 0.041* | |
C12 | 0.4239 (5) | 0.1438 (4) | 0.3957 (2) | 0.0348 (8) | |
C13 | 0.2048 (6) | 0.0631 (5) | 0.3885 (2) | 0.0444 (9) | |
H13 | 0.1055 | 0.0734 | 0.4348 | 0.053* | |
C14 | 0.1380 (6) | −0.0292 (4) | 0.3146 (2) | 0.0454 (9) | |
H14 | −0.0052 | −0.0841 | 0.3118 | 0.055* | |
C15 | 0.2162 (6) | −0.1383 (4) | 0.1639 (3) | 0.0479 (10) | |
H15 | 0.0738 | −0.1944 | 0.1591 | 0.057* | |
C16 | 0.3583 (7) | −0.1484 (5) | 0.0960 (3) | 0.0541 (11) | |
H16 | 0.3127 | −0.2109 | 0.0451 | 0.065* | |
C17 | 0.5745 (7) | −0.0651 (5) | 0.1018 (2) | 0.0493 (10) | |
H17 | 0.6712 | −0.0727 | 0.0546 | 0.059* | |
C18 | 0.6430 (6) | 0.0265 (4) | 0.1759 (2) | 0.0403 (9) | |
H18 | 0.7867 | 0.0808 | 0.1792 | 0.048* | |
C19 | 0.4979 (5) | 0.0400 (4) | 0.2482 (2) | 0.0334 (8) | |
C20 | 0.2798 (6) | −0.0440 (4) | 0.2422 (2) | 0.0376 (8) | |
C31 | 0.2512 (5) | 0.4230 (4) | 0.6895 (2) | 0.0345 (8) | |
C32 | 0.3290 (5) | 0.4328 (4) | 0.7740 (2) | 0.0398 (9) | |
H32 | 0.4694 | 0.3885 | 0.7856 | 0.048* | |
C33 | 0.2048 (5) | 0.5061 (4) | 0.8411 (2) | 0.0402 (9) | |
H33 | 0.2596 | 0.5107 | 0.8973 | 0.048* | |
C34 | −0.0016 (5) | 0.5723 (4) | 0.8236 (2) | 0.0360 (8) | |
Br34 | −0.17324 (8) | 0.67362 (6) | 0.91526 (3) | 0.06341 (18) | |
C35 | −0.0841 (5) | 0.5658 (4) | 0.7406 (2) | 0.0387 (9) | |
H35 | −0.2238 | 0.6115 | 0.7295 | 0.046* | |
C36 | 0.0415 (5) | 0.4912 (4) | 0.6743 (2) | 0.0397 (9) | |
H36 | −0.0149 | 0.4863 | 0.6183 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.041 (2) | 0.049 (2) | 0.036 (2) | 0.0112 (19) | 0.0044 (17) | 0.0078 (18) |
O1 | 0.0424 (16) | 0.083 (2) | 0.0434 (15) | 0.0066 (14) | 0.0013 (12) | −0.0014 (14) |
C2 | 0.040 (2) | 0.057 (3) | 0.040 (2) | 0.0099 (18) | 0.0015 (17) | −0.0001 (19) |
C3 | 0.036 (2) | 0.048 (2) | 0.039 (2) | 0.0035 (17) | 0.0025 (17) | 0.0061 (18) |
C11 | 0.0291 (18) | 0.032 (2) | 0.041 (2) | 0.0014 (15) | 0.0002 (16) | 0.0047 (17) |
C12 | 0.0329 (19) | 0.039 (2) | 0.033 (2) | 0.0062 (16) | 0.0026 (16) | 0.0052 (17) |
C13 | 0.038 (2) | 0.050 (2) | 0.047 (2) | 0.0055 (18) | 0.0140 (18) | 0.013 (2) |
C14 | 0.033 (2) | 0.039 (2) | 0.064 (3) | 0.0000 (17) | 0.0039 (19) | 0.008 (2) |
C15 | 0.042 (2) | 0.035 (2) | 0.066 (3) | 0.0021 (17) | −0.017 (2) | −0.001 (2) |
C16 | 0.069 (3) | 0.044 (2) | 0.049 (3) | 0.014 (2) | −0.012 (2) | −0.005 (2) |
C17 | 0.058 (3) | 0.051 (2) | 0.040 (2) | 0.018 (2) | 0.0063 (19) | 0.003 (2) |
C18 | 0.040 (2) | 0.041 (2) | 0.040 (2) | 0.0052 (17) | 0.0028 (17) | 0.0006 (18) |
C19 | 0.036 (2) | 0.0306 (19) | 0.034 (2) | 0.0073 (16) | −0.0022 (16) | 0.0044 (16) |
C20 | 0.035 (2) | 0.030 (2) | 0.049 (2) | 0.0027 (16) | −0.0056 (17) | 0.0034 (18) |
C31 | 0.0363 (19) | 0.032 (2) | 0.035 (2) | 0.0004 (16) | 0.0020 (16) | 0.0039 (16) |
C32 | 0.0321 (19) | 0.045 (2) | 0.043 (2) | 0.0045 (16) | −0.0002 (17) | 0.0077 (18) |
C33 | 0.041 (2) | 0.044 (2) | 0.036 (2) | 0.0011 (17) | −0.0035 (17) | 0.0019 (17) |
C34 | 0.0357 (19) | 0.031 (2) | 0.041 (2) | −0.0026 (16) | 0.0027 (16) | 0.0002 (17) |
Br34 | 0.0648 (3) | 0.0676 (3) | 0.0562 (3) | 0.0145 (2) | 0.0149 (2) | −0.0101 (2) |
C35 | 0.0284 (18) | 0.041 (2) | 0.048 (2) | 0.0027 (16) | 0.0000 (17) | 0.0092 (18) |
C36 | 0.038 (2) | 0.046 (2) | 0.035 (2) | 0.0016 (17) | −0.0016 (16) | 0.0061 (18) |
C1—O1 | 1.221 (4) | C16—C17 | 1.405 (5) |
C1—C2 | 1.473 (5) | C16—H16 | 0.9300 |
C1—C12 | 1.485 (5) | C17—C18 | 1.359 (5) |
C2—C3 | 1.314 (4) | C17—H17 | 0.9300 |
C2—H2 | 0.9300 | C18—C19 | 1.414 (4) |
C3—C31 | 1.456 (4) | C18—H18 | 0.9300 |
C3—H3 | 0.9300 | C19—C20 | 1.417 (4) |
C11—C12 | 1.363 (4) | C31—C32 | 1.388 (4) |
C11—C19 | 1.403 (4) | C31—C36 | 1.389 (4) |
C11—H11 | 0.9300 | C32—C33 | 1.375 (4) |
C12—C13 | 1.413 (5) | C32—H32 | 0.9300 |
C13—C14 | 1.355 (5) | C33—C34 | 1.373 (4) |
C13—H13 | 0.9300 | C33—H33 | 0.9300 |
C14—C20 | 1.405 (5) | C34—C35 | 1.375 (4) |
C14—H14 | 0.9300 | C34—Br34 | 1.889 (3) |
C15—C16 | 1.349 (5) | C35—C36 | 1.375 (4) |
C15—C20 | 1.413 (5) | C35—H35 | 0.9300 |
C15—H15 | 0.9300 | C36—H36 | 0.9300 |
O1—C1—C2 | 121.0 (3) | C16—C17—H17 | 119.9 |
O1—C1—C12 | 120.2 (3) | C17—C18—C19 | 120.6 (3) |
C2—C1—C12 | 118.9 (3) | C17—C18—H18 | 119.7 |
C3—C2—C1 | 121.8 (3) | C19—C18—H18 | 119.7 |
C3—C2—H2 | 119.1 | C11—C19—C18 | 122.3 (3) |
C1—C2—H2 | 119.1 | C11—C19—C20 | 118.7 (3) |
C2—C3—C31 | 128.3 (3) | C18—C19—C20 | 119.0 (3) |
C2—C3—H3 | 115.9 | C14—C20—C15 | 123.4 (3) |
C31—C3—H3 | 115.9 | C14—C20—C19 | 118.2 (3) |
C12—C11—C19 | 122.1 (3) | C15—C20—C19 | 118.4 (3) |
C12—C11—H11 | 118.9 | C32—C31—C36 | 117.6 (3) |
C19—C11—H11 | 118.9 | C32—C31—C3 | 119.3 (3) |
C11—C12—C13 | 118.7 (3) | C36—C31—C3 | 123.1 (3) |
C11—C12—C1 | 119.5 (3) | C33—C32—C31 | 122.0 (3) |
C13—C12—C1 | 121.8 (3) | C33—C32—H32 | 119.0 |
C14—C13—C12 | 120.6 (3) | C31—C32—H32 | 119.0 |
C14—C13—H13 | 119.7 | C34—C33—C32 | 118.8 (3) |
C12—C13—H13 | 119.7 | C34—C33—H33 | 120.6 |
C13—C14—C20 | 121.7 (3) | C32—C33—H33 | 120.6 |
C13—C14—H14 | 119.2 | C33—C34—C35 | 121.0 (3) |
C20—C14—H14 | 119.2 | C33—C34—Br34 | 119.1 (3) |
C16—C15—C20 | 121.2 (4) | C35—C34—Br34 | 119.9 (2) |
C16—C15—H15 | 119.4 | C36—C35—C34 | 119.5 (3) |
C20—C15—H15 | 119.4 | C36—C35—H35 | 120.2 |
C15—C16—C17 | 120.5 (4) | C34—C35—H35 | 120.2 |
C15—C16—H16 | 119.8 | C35—C36—C31 | 121.1 (3) |
C17—C16—H16 | 119.8 | C35—C36—H36 | 119.4 |
C18—C17—C16 | 120.3 (3) | C31—C36—H36 | 119.4 |
C18—C17—H17 | 119.9 | ||
O1—C1—C2—C3 | −19.8 (6) | C13—C14—C20—C19 | 0.3 (5) |
C12—C1—C2—C3 | 161.6 (3) | C16—C15—C20—C14 | 179.8 (3) |
C1—C2—C3—C31 | 176.8 (3) | C16—C15—C20—C19 | −0.2 (5) |
C19—C11—C12—C13 | 1.1 (5) | C11—C19—C20—C14 | 1.9 (4) |
C19—C11—C12—C1 | 178.8 (3) | C18—C19—C20—C14 | 180.0 (3) |
O1—C1—C12—C11 | −19.9 (5) | C11—C19—C20—C15 | −178.1 (3) |
C2—C1—C12—C11 | 158.6 (3) | C18—C19—C20—C15 | 0.0 (5) |
O1—C1—C12—C13 | 157.7 (3) | C2—C3—C31—C32 | 169.5 (4) |
C2—C1—C12—C13 | −23.7 (5) | C2—C3—C31—C36 | −12.4 (6) |
C11—C12—C13—C14 | 1.2 (5) | C36—C31—C32—C33 | 0.3 (5) |
C1—C12—C13—C14 | −176.4 (3) | C3—C31—C32—C33 | 178.5 (3) |
C12—C13—C14—C20 | −1.9 (5) | C31—C32—C33—C34 | −0.4 (5) |
C20—C15—C16—C17 | 0.1 (5) | C32—C33—C34—C35 | 0.1 (5) |
C15—C16—C17—C18 | 0.1 (5) | C32—C33—C34—Br34 | −179.9 (2) |
C16—C17—C18—C19 | −0.3 (5) | C33—C34—C35—C36 | 0.3 (5) |
C12—C11—C19—C18 | 179.3 (3) | Br34—C34—C35—C36 | −179.7 (2) |
C12—C11—C19—C20 | −2.6 (5) | C34—C35—C36—C31 | −0.4 (5) |
C17—C18—C19—C11 | 178.3 (3) | C32—C31—C36—C35 | 0.0 (5) |
C17—C18—C19—C20 | 0.2 (5) | C3—C31—C36—C35 | −178.0 (3) |
C13—C14—C20—C15 | −179.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C32—H32···Cg4i | 0.93 | 2.85 | 3.513 (3) | 129 |
Symmetry code: (i) −x+1, −y, −z+1. |
C17H12OS | Z = 2 |
Mr = 264.33 | F(000) = 276 |
Triclinic, P1 | Dx = 1.360 Mg m−3 |
a = 5.8271 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.4489 (4) Å | Cell parameters from 4247 reflections |
c = 15.2068 (9) Å | θ = 1.4–32.6° |
α = 79.745 (3)° | µ = 0.24 mm−1 |
β = 84.427 (3)° | T = 296 K |
γ = 85.763 (3)° | Block, colourless |
V = 645.36 (6) Å3 | 0.25 × 0.20 × 0.15 mm |
Bruker Kappa APEXII diffractometer | 2164 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.033 |
φ and ω scans | θmax = 26.6°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −7→7 |
Tmin = 0.933, Tmax = 0.965 | k = −9→9 |
18170 measured reflections | l = −19→19 |
2694 independent reflections |
Refinement on F2 | 15 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.0278P)2 + 0.8674P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
2694 reflections | Δρmax = 0.23 e Å−3 |
185 parameters | Δρmin = −0.41 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.9718 (5) | 0.2608 (4) | 0.50120 (19) | 0.0423 (7) | |
O1 | 1.1716 (4) | 0.2701 (4) | 0.51604 (15) | 0.0639 (7) | |
C11 | 1.0710 (4) | 0.3045 (3) | 0.33771 (18) | 0.0349 (6) | |
H11 | 1.2055 | 0.3543 | 0.3481 | 0.042* | |
C12 | 0.9152 (4) | 0.2463 (3) | 0.40887 (18) | 0.0363 (6) | |
C13 | 0.7111 (5) | 0.1705 (4) | 0.3930 (2) | 0.0430 (7) | |
H13 | 0.6026 | 0.1340 | 0.4407 | 0.052* | |
C14 | 0.6715 (5) | 0.1503 (4) | 0.3085 (2) | 0.0450 (7) | |
H14 | 0.5383 | 0.0965 | 0.2997 | 0.054* | |
C15 | 0.7924 (5) | 0.1952 (4) | 0.1456 (2) | 0.0477 (7) | |
H15 | 0.6608 | 0.1423 | 0.1345 | 0.057* | |
C16 | 0.9447 (6) | 0.2570 (5) | 0.0761 (2) | 0.0549 (8) | |
H16 | 0.9177 | 0.2450 | 0.0182 | 0.066* | |
C17 | 1.1423 (6) | 0.3388 (4) | 0.0905 (2) | 0.0507 (8) | |
H17 | 1.2449 | 0.3829 | 0.0420 | 0.061* | |
C18 | 1.1860 (5) | 0.3546 (4) | 0.17489 (19) | 0.0395 (6) | |
H18 | 1.3192 | 0.4084 | 0.1836 | 0.047* | |
C19 | 1.0318 (4) | 0.2905 (3) | 0.24950 (18) | 0.0343 (6) | |
C20 | 0.8275 (4) | 0.2088 (3) | 0.23435 (19) | 0.0372 (6) | |
C2 | 0.7821 (5) | 0.2641 (4) | 0.57262 (19) | 0.0426 (7) | 0.780 (3) |
H2 | 0.6316 | 0.2953 | 0.5577 | 0.051* | 0.780 (3) |
C3 | 0.8251 (5) | 0.2231 (4) | 0.65741 (19) | 0.0406 (6) | 0.780 (3) |
H3 | 0.9761 | 0.1831 | 0.6687 | 0.049* | 0.780 (3) |
C32 | 0.6634 (4) | 0.2334 (3) | 0.73499 (18) | 0.0368 (6) | 0.780 (3) |
S31 | 0.3958 (2) | 0.33969 (18) | 0.72951 (8) | 0.0440 (3) | 0.780 (3) |
C33 | 0.7012 (11) | 0.1705 (10) | 0.8224 (4) | 0.0429 (13) | 0.780 (3) |
H33 | 0.8370 | 0.1056 | 0.8395 | 0.051* | 0.780 (3) |
C34 | 0.5200 (8) | 0.2109 (16) | 0.8849 (3) | 0.0480 (13) | 0.780 (3) |
H34 | 0.5217 | 0.1784 | 0.9468 | 0.058* | 0.780 (3) |
C35 | 0.3430 (8) | 0.3035 (10) | 0.8425 (3) | 0.0471 (12) | 0.780 (3) |
H35 | 0.2067 | 0.3431 | 0.8721 | 0.057* | 0.780 (3) |
C2A | 0.7821 (5) | 0.2641 (4) | 0.57262 (19) | 0.0426 (7) | 0.220 (3) |
H2A | 0.6316 | 0.2953 | 0.5577 | 0.051* | 0.220 (3) |
C3A | 0.8251 (5) | 0.2231 (4) | 0.65741 (19) | 0.0406 (6) | 0.220 (3) |
H3A | 0.9761 | 0.1831 | 0.6687 | 0.049* | 0.220 (3) |
C42 | 0.6634 (4) | 0.2334 (3) | 0.73499 (18) | 0.0368 (6) | 0.220 (3) |
S41 | 0.7334 (11) | 0.1491 (11) | 0.8392 (3) | 0.0440 (3) | 0.220 (3) |
C43 | 0.4393 (19) | 0.299 (3) | 0.7365 (8) | 0.0440 (3) | 0.220 (3) |
H43 | 0.3681 | 0.3486 | 0.6847 | 0.053* | 0.220 (3) |
C44 | 0.324 (2) | 0.287 (4) | 0.8227 (9) | 0.0471 (12) | 0.220 (3) |
H44 | 0.1725 | 0.3285 | 0.8352 | 0.057* | 0.220 (3) |
C45 | 0.467 (3) | 0.205 (6) | 0.8851 (8) | 0.0480 (13) | 0.220 (3) |
H45 | 0.4230 | 0.1821 | 0.9463 | 0.058* | 0.220 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0371 (15) | 0.0436 (16) | 0.0433 (16) | −0.0010 (12) | −0.0020 (12) | −0.0009 (12) |
O1 | 0.0390 (12) | 0.103 (2) | 0.0475 (13) | −0.0079 (12) | −0.0034 (10) | −0.0067 (13) |
C11 | 0.0281 (12) | 0.0329 (13) | 0.0441 (15) | −0.0036 (10) | −0.0003 (11) | −0.0084 (11) |
C12 | 0.0326 (13) | 0.0319 (13) | 0.0430 (15) | 0.0007 (10) | −0.0003 (11) | −0.0051 (11) |
C13 | 0.0337 (14) | 0.0387 (15) | 0.0532 (18) | −0.0063 (11) | 0.0049 (12) | −0.0018 (13) |
C14 | 0.0321 (14) | 0.0387 (15) | 0.067 (2) | −0.0068 (12) | −0.0059 (13) | −0.0144 (14) |
C15 | 0.0404 (16) | 0.0443 (17) | 0.064 (2) | 0.0020 (13) | −0.0166 (14) | −0.0191 (15) |
C16 | 0.058 (2) | 0.060 (2) | 0.0501 (19) | 0.0077 (16) | −0.0144 (15) | −0.0189 (16) |
C17 | 0.0536 (18) | 0.0493 (18) | 0.0467 (18) | 0.0039 (14) | 0.0027 (14) | −0.0077 (14) |
C18 | 0.0372 (14) | 0.0366 (14) | 0.0443 (16) | −0.0015 (11) | −0.0028 (12) | −0.0065 (12) |
C19 | 0.0299 (12) | 0.0274 (12) | 0.0444 (15) | 0.0034 (10) | −0.0032 (11) | −0.0051 (11) |
C20 | 0.0331 (13) | 0.0291 (13) | 0.0497 (16) | 0.0041 (10) | −0.0043 (11) | −0.0095 (11) |
C2 | 0.0357 (14) | 0.0468 (16) | 0.0445 (16) | 0.0018 (12) | −0.0035 (12) | −0.0072 (13) |
C3 | 0.0340 (14) | 0.0381 (15) | 0.0494 (17) | −0.0011 (11) | 0.0004 (12) | −0.0096 (12) |
C32 | 0.0355 (14) | 0.0326 (13) | 0.0439 (15) | −0.0065 (11) | −0.0021 (11) | −0.0096 (11) |
S31 | 0.0347 (6) | 0.0467 (8) | 0.0509 (6) | 0.0066 (4) | −0.0080 (4) | −0.0109 (4) |
C33 | 0.044 (3) | 0.041 (3) | 0.043 (3) | 0.005 (2) | −0.020 (2) | 0.000 (2) |
C34 | 0.057 (3) | 0.047 (2) | 0.0410 (17) | −0.015 (4) | 0.0007 (17) | −0.0066 (14) |
C35 | 0.0433 (18) | 0.047 (2) | 0.056 (3) | −0.0085 (17) | 0.0066 (18) | −0.025 (2) |
C2A | 0.0357 (14) | 0.0468 (16) | 0.0445 (16) | 0.0018 (12) | −0.0035 (12) | −0.0072 (13) |
C3A | 0.0340 (14) | 0.0381 (15) | 0.0494 (17) | −0.0011 (11) | 0.0004 (12) | −0.0096 (12) |
C42 | 0.0355 (14) | 0.0326 (13) | 0.0439 (15) | −0.0065 (11) | −0.0021 (11) | −0.0096 (11) |
S41 | 0.0347 (6) | 0.0467 (8) | 0.0509 (6) | 0.0066 (4) | −0.0080 (4) | −0.0109 (4) |
C43 | 0.0347 (6) | 0.0467 (8) | 0.0509 (6) | 0.0066 (4) | −0.0080 (4) | −0.0109 (4) |
C44 | 0.0433 (18) | 0.047 (2) | 0.056 (3) | −0.0085 (17) | 0.0066 (18) | −0.025 (2) |
C45 | 0.057 (3) | 0.047 (2) | 0.0410 (17) | −0.015 (4) | 0.0007 (17) | −0.0066 (14) |
C1—O1 | 1.217 (3) | C19—C20 | 1.432 (4) |
C1—C2 | 1.474 (4) | C2—C3 | 1.315 (4) |
C1—C12 | 1.497 (4) | C2—H2 | 0.9300 |
C11—C12 | 1.372 (4) | C3—C32 | 1.446 (4) |
C11—C19 | 1.405 (4) | C3—H3 | 0.9300 |
C11—H11 | 0.9300 | C32—C33 | 1.363 (6) |
C12—C13 | 1.413 (4) | C32—S31 | 1.698 (2) |
C13—C14 | 1.364 (4) | S31—C35 | 1.692 (5) |
C13—H13 | 0.9300 | C33—C34 | 1.403 (7) |
C14—C20 | 1.404 (4) | C33—H33 | 0.9300 |
C14—H14 | 0.9300 | C34—C35 | 1.350 (5) |
C15—C16 | 1.350 (5) | C34—H34 | 0.9300 |
C15—C20 | 1.407 (4) | C35—H35 | 0.9300 |
C15—H15 | 0.9300 | S41—C45 | 1.695 (7) |
C16—C17 | 1.395 (5) | C43—C44 | 1.404 (9) |
C16—H16 | 0.9300 | C43—H43 | 0.9300 |
C17—C18 | 1.359 (4) | C44—C45 | 1.352 (7) |
C17—H17 | 0.9300 | C44—H44 | 0.9300 |
C18—C19 | 1.413 (4) | C45—H45 | 0.9300 |
C18—H18 | 0.9300 | ||
O1—C1—C2 | 121.2 (3) | C14—C20—C15 | 123.7 (3) |
O1—C1—C12 | 119.8 (3) | C14—C20—C19 | 118.3 (3) |
C2—C1—C12 | 118.9 (2) | C15—C20—C19 | 118.0 (3) |
C12—C11—C19 | 121.5 (2) | C3—C2—C1 | 120.2 (3) |
C12—C11—H11 | 119.3 | C3—C2—H2 | 119.9 |
C19—C11—H11 | 119.3 | C1—C2—H2 | 119.9 |
C11—C12—C13 | 119.2 (3) | C2—C3—C32 | 127.2 (2) |
C11—C12—C1 | 118.5 (2) | C2—C3—H3 | 116.4 |
C13—C12—C1 | 122.3 (2) | C32—C3—H3 | 116.4 |
C14—C13—C12 | 120.6 (3) | C33—C32—C3 | 126.9 (3) |
C14—C13—H13 | 119.7 | C33—C32—S31 | 109.4 (3) |
C12—C13—H13 | 119.7 | C3—C32—S31 | 123.67 (19) |
C13—C14—C20 | 121.4 (3) | C35—S31—C32 | 92.48 (19) |
C13—C14—H14 | 119.3 | C32—C33—C34 | 115.0 (5) |
C20—C14—H14 | 119.3 | C32—C33—H33 | 122.5 |
C16—C15—C20 | 121.7 (3) | C34—C33—H33 | 122.5 |
C16—C15—H15 | 119.1 | C35—C34—C33 | 110.4 (5) |
C20—C15—H15 | 119.1 | C35—C34—H34 | 124.8 |
C15—C16—C17 | 120.4 (3) | C33—C34—H34 | 124.8 |
C15—C16—H16 | 119.8 | C34—C35—S31 | 112.7 (4) |
C17—C16—H16 | 119.8 | C34—C35—H35 | 123.6 |
C18—C17—C16 | 120.4 (3) | S31—C35—H35 | 123.6 |
C18—C17—H17 | 119.8 | C44—C43—H43 | 122.8 |
C16—C17—H17 | 119.8 | C45—C44—C43 | 110.2 (8) |
C17—C18—C19 | 120.9 (3) | C45—C44—H44 | 124.9 |
C17—C18—H18 | 119.6 | C43—C44—H44 | 124.9 |
C19—C18—H18 | 119.6 | C44—C45—S41 | 112.5 (7) |
C11—C19—C18 | 122.5 (2) | C44—C45—H45 | 123.8 |
C11—C19—C20 | 118.9 (2) | S41—C45—H45 | 123.8 |
C18—C19—C20 | 118.6 (3) | ||
C19—C11—C12—C13 | 0.1 (4) | C16—C15—C20—C19 | −0.2 (4) |
C19—C11—C12—C1 | 178.3 (2) | C11—C19—C20—C14 | 1.6 (4) |
O1—C1—C12—C11 | −21.7 (4) | C18—C19—C20—C14 | −178.1 (2) |
C2—C1—C12—C11 | 158.1 (3) | C11—C19—C20—C15 | −179.6 (2) |
O1—C1—C12—C13 | 156.5 (3) | C18—C19—C20—C15 | 0.6 (4) |
C2—C1—C12—C13 | −23.7 (4) | O1—C1—C2—C3 | −20.2 (5) |
C11—C12—C13—C14 | 1.8 (4) | C12—C1—C2—C3 | 160.0 (3) |
C1—C12—C13—C14 | −176.3 (3) | C1—C2—C3—C32 | 174.8 (3) |
C12—C13—C14—C20 | −2.0 (4) | C2—C3—C32—C33 | 171.5 (5) |
C20—C15—C16—C17 | −0.7 (5) | C2—C3—C32—S31 | −12.1 (4) |
C15—C16—C17—C18 | 1.1 (5) | C33—C32—S31—C35 | 1.4 (4) |
C16—C17—C18—C19 | −0.6 (4) | C3—C32—S31—C35 | −175.6 (3) |
C12—C11—C19—C18 | 178.0 (2) | C3—C32—C33—C34 | 175.3 (6) |
C12—C11—C19—C20 | −1.8 (4) | S31—C32—C33—C34 | −1.5 (8) |
C17—C18—C19—C11 | −180.0 (3) | C32—C33—C34—C35 | 0.9 (11) |
C17—C18—C19—C20 | −0.2 (4) | C33—C34—C35—S31 | 0.2 (10) |
C13—C14—C20—C15 | −178.4 (3) | C32—S31—C35—C34 | −0.9 (6) |
C13—C14—C20—C19 | 0.3 (4) | C43—C44—C45—S41 | 1 (4) |
C16—C15—C20—C14 | 178.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···Cg5i | 0.93 | 2.80 | 3.572 (4) | 141 |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Parameter | (I) | (I) | (II) | (III) | |
x = | 1 | 2 | nil | nil | |
Cx2—Cx1—Cx12—Cx11 | 155.7 (2) | 151.6 (2) | 158.6 (3) | 158.1 (3) | |
Cx2—Cx3—Cx31—Cx32 | 169.7 (2) | 167.2 (2) | 169.5 (4) | ||
Cx2—Cx3—Cx32—Cx33 | 171.1 (5) | ||||
Cx2—Cx3—Cx32—Sx41 | 171.3 (4) |
Compound | D—H···A | D—H | H···A | D···A | D—H···A | |
(I) | C132—H132···Cg1i | 0.93 | 2.88 | 3.557 (3) | 131 | |
C135—H135···Cg2ii | 0.93 | 2.83 | 3.503 (3) | 130 | ||
C214—H214···Cg3ii | 0.93 | 2.87 | 3.554 (2) | 131 | ||
(II) | C32—H32···Cg4iii | 0.93 | 2.85 | 3.513 (3) | 129 | |
(III) | C18—H18···Cg5iv | 0.93 | 2.80 | 3.572 (4) | 141 |
Symmetry codes:
(i) -x+1, -y+1, -z+1;
(ii) -x, -y+1, -z+1;
(iii) -x+1, -y, -z+1;
(iv) -x+2, -y+1, -z+1. Cg1–Cg5 represent the centroids of the C115–C120, C231–C236, C111–C114/C120/C119, C15–C20 and S31/C32–C35 rings, respectively |
C—Br···Cg | C—Br | Br···Cg | C···Cg | C—Br···Cg | |
C34—Br34···Cg4ii | 1.889 (3) | 3.7527 (15) | 4.620 (3) | 105.13 (10) |
Symmetry code: (ii) -x, -y+1, -z+1. Cg4 represents the centroid of the C15–C20 ring. |