Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010000963X/qa0351sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010000963X/qa0351Isup2.hkl |
CCDC reference: 150379
A solution of [{IPr)2—ATI}In(Me)(Nme2Ph)][MeB(C6F5)3] in C6D5Cl was exposed to air. Hexane was added and the mixture was maintained at 296 K whereupon yellow crystals of (I) formed.
The disordered C12, C13, C14, C12', C13' and C14' atoms were refined isotropically. Some restraints were used to ensure the disordered isopropyl groups have idealized geometries.
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; software used to prepare material for publication: SHELXTL.
[In(CH3)(C18HBF15O)(C13H19N2)] | F(000) = 3408 |
Mr = 862.15 | Dx = 1.761 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 19.6683 (16) Å | Cell parameters from 6872 reflections |
b = 18.7739 (16) Å | θ = 2–27° |
c = 19.8049 (17) Å | µ = 0.84 mm−1 |
β = 117.201 (1)° | T = 183 K |
V = 6504.2 (9) Å3 | Block, yellow |
Z = 8 | 0.43 × 0.40 × 0.36 mm |
Bruker CCD-1000 area-detector diffractometer | 13220 independent reflections |
Radiation source: fine-focus sealed tube | 9101 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω scans | θmax = 26.4°, θmin = 2.1° |
Absorption correction: empirical (using intensity measurements) (SADABS; Blessing, 1995) | h = −24→21 |
Tmin = 0.713, Tmax = 0.751 | k = 0→23 |
41003 measured reflections | l = 0→24 |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.035P)2] where P = (Fo2 + 2Fc2)/3 |
13220 reflections | (Δ/σ)max = 0.002 |
947 parameters | Δρmax = 0.68 e Å−3 |
12 restraints | Δρmin = −0.68 e Å−3 |
[In(CH3)(C18HBF15O)(C13H19N2)] | V = 6504.2 (9) Å3 |
Mr = 862.15 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 19.6683 (16) Å | µ = 0.84 mm−1 |
b = 18.7739 (16) Å | T = 183 K |
c = 19.8049 (17) Å | 0.43 × 0.40 × 0.36 mm |
β = 117.201 (1)° |
Bruker CCD-1000 area-detector diffractometer | 13220 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Blessing, 1995) | 9101 reflections with I > 2σ(I) |
Tmin = 0.713, Tmax = 0.751 | Rint = 0.029 |
41003 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 12 restraints |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.68 e Å−3 |
13220 reflections | Δρmin = −0.68 e Å−3 |
947 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
In1 | 1.015483 (11) | 0.713348 (10) | 0.998920 (11) | 0.02628 (6) | |
In2 | 0.503805 (10) | 0.788991 (10) | −0.020258 (10) | 0.02637 (6) | |
N1 | 0.94431 (12) | 0.79470 (11) | 0.93008 (11) | 0.0260 (5) | |
N2 | 1.03891 (13) | 0.79699 (11) | 1.07708 (12) | 0.0316 (6) | |
N1A | 0.44661 (13) | 0.70280 (11) | −0.09124 (13) | 0.0309 (5) | |
N2A | 0.50530 (13) | 0.71288 (13) | 0.05795 (13) | 0.0354 (6) | |
F17 | 0.75550 (10) | 0.72086 (9) | 0.86816 (9) | 0.0429 (4) | |
F18 | 0.70583 (10) | 0.85268 (9) | 0.86512 (10) | 0.0535 (5) | |
F19 | 0.74885 (9) | 0.92815 (9) | 0.99503 (10) | 0.0459 (5) | |
F20 | 0.84702 (10) | 0.86762 (8) | 1.13070 (9) | 0.0457 (4) | |
F21 | 0.89841 (9) | 0.73727 (8) | 1.13543 (8) | 0.0371 (4) | |
F23 | 0.75303 (9) | 0.66180 (9) | 1.08501 (9) | 0.0422 (4) | |
F24 | 0.75438 (10) | 0.58948 (9) | 1.20039 (10) | 0.0456 (5) | |
F25 | 0.84978 (10) | 0.47772 (9) | 1.26216 (9) | 0.0435 (4) | |
F26 | 0.95128 (10) | 0.44280 (9) | 1.20889 (9) | 0.0443 (4) | |
F27 | 0.95798 (9) | 0.51869 (8) | 1.09892 (9) | 0.0384 (4) | |
F29 | 0.69226 (10) | 0.62495 (11) | 0.92732 (10) | 0.0538 (5) | |
F30 | 0.61251 (12) | 0.53756 (13) | 0.81295 (11) | 0.0820 (8) | |
F31 | 0.68487 (14) | 0.43811 (11) | 0.76838 (11) | 0.0833 (8) | |
F32 | 0.84105 (14) | 0.43371 (10) | 0.83893 (10) | 0.0721 (7) | |
F33 | 0.92185 (11) | 0.52825 (10) | 0.94318 (10) | 0.0522 (5) | |
F17A | 0.36499 (9) | 0.77753 (8) | 0.11615 (8) | 0.0394 (4) | |
F18A | 0.31450 (10) | 0.64638 (9) | 0.11086 (10) | 0.0490 (5) | |
F19A | 0.24213 (9) | 0.57539 (9) | −0.02309 (10) | 0.0459 (5) | |
F20A | 0.22260 (10) | 0.64096 (9) | −0.15385 (9) | 0.0469 (5) | |
F21A | 0.27231 (9) | 0.77336 (8) | −0.15037 (8) | 0.0369 (4) | |
F23A | 0.16799 (8) | 0.84428 (8) | −0.10584 (9) | 0.0351 (4) | |
F24A | 0.06910 (8) | 0.92511 (9) | −0.21657 (9) | 0.0398 (4) | |
F25A | 0.11547 (9) | 1.04498 (8) | −0.26084 (9) | 0.0428 (4) | |
F26A | 0.26676 (10) | 1.08054 (8) | −0.19236 (9) | 0.0441 (4) | |
F27A | 0.36855 (9) | 0.99725 (8) | −0.08597 (9) | 0.0374 (4) | |
F29A | 0.25001 (9) | 0.88008 (10) | 0.05777 (9) | 0.0448 (5) | |
F30A | 0.28097 (13) | 0.95339 (13) | 0.18408 (11) | 0.0785 (7) | |
F31A | 0.40747 (14) | 1.03719 (11) | 0.24812 (11) | 0.0932 (9) | |
F32A | 0.50439 (12) | 1.04275 (10) | 0.18476 (11) | 0.0815 (8) | |
F33A | 0.48049 (10) | 0.96421 (10) | 0.06563 (10) | 0.0544 (5) | |
B1 | 0.85937 (17) | 0.63728 (16) | 1.01283 (17) | 0.0247 (7) | |
B2 | 0.34232 (17) | 0.86802 (17) | −0.02158 (17) | 0.0257 (7) | |
C1 | 1.08842 (18) | 0.64352 (16) | 0.9786 (2) | 0.0500 (9) | |
H1A | 1.0609 | 0.5995 | 0.9556 | 0.075* | |
H1B | 1.1332 | 0.6324 | 1.0268 | 0.075* | |
H1C | 1.1050 | 0.6663 | 0.9442 | 0.075* | |
C2 | 0.90591 (17) | 0.78923 (15) | 0.84605 (15) | 0.0344 (7) | |
H2 | 0.8545 | 0.8123 | 0.8255 | 0.041* | |
C3 | 0.89599 (19) | 0.71101 (16) | 0.82333 (17) | 0.0474 (8) | |
H3A | 0.9463 | 0.6892 | 0.8395 | 0.071* | |
H3B | 0.8662 | 0.7071 | 0.7681 | 0.071* | |
H3C | 0.8691 | 0.6864 | 0.8478 | 0.071* | |
C4 | 0.95367 (18) | 0.82756 (17) | 0.81453 (16) | 0.0443 (8) | |
H4A | 0.9601 | 0.8776 | 0.8304 | 0.067* | |
H4B | 0.9277 | 0.8249 | 0.7590 | 0.067* | |
H4C | 1.0039 | 0.8048 | 0.8339 | 0.067* | |
C5 | 0.94310 (14) | 0.85442 (13) | 0.96655 (14) | 0.0241 (6) | |
C6 | 0.89955 (16) | 0.91399 (15) | 0.92702 (16) | 0.0341 (7) | |
H6 | 0.8741 | 0.9075 | 0.8735 | 0.041* | |
C7 | 0.88599 (17) | 0.98002 (15) | 0.94971 (18) | 0.0400 (8) | |
H7 | 0.8550 | 1.0112 | 0.9096 | 0.048* | |
C8 | 0.91096 (18) | 1.00737 (16) | 1.0224 (2) | 0.0448 (8) | |
H8 | 0.8939 | 1.0537 | 1.0267 | 0.054* | |
C9 | 0.95805 (17) | 0.97308 (17) | 1.08820 (19) | 0.0435 (8) | |
H9 | 0.9682 | 0.9985 | 1.1333 | 0.052* | |
C10 | 0.99322 (16) | 0.90751 (15) | 1.09962 (16) | 0.0347 (7) | |
H10 | 1.0239 | 0.8964 | 1.1517 | 0.042* | |
C11 | 0.99308 (15) | 0.85364 (14) | 1.05024 (14) | 0.0249 (6) | |
C12 | 1.1035 (2) | 0.7939 (2) | 1.1546 (3) | 0.0336 (9)* | 0.725 (5) |
H12 | 1.1180 | 0.8436 | 1.1740 | 0.040* | 0.725 (5) |
C13 | 1.17198 (15) | 0.7582 (2) | 1.1535 (2) | 0.0487 (13)* | 0.725 (5) |
H13A | 1.1592 | 0.7088 | 1.1365 | 0.073* | 0.725 (5) |
H13B | 1.2150 | 0.7590 | 1.2048 | 0.073* | 0.725 (5) |
H13C | 1.1861 | 0.7838 | 1.1187 | 0.073* | 0.725 (5) |
C14 | 1.0798 (2) | 0.7540 (2) | 1.20698 (18) | 0.0492 (13)* | 0.725 (5) |
H14A | 1.0384 | 0.7798 | 1.2106 | 0.074* | 0.725 (5) |
H14B | 1.1236 | 0.7502 | 1.2575 | 0.074* | 0.725 (5) |
H14C | 1.0622 | 0.7062 | 1.1867 | 0.074* | 0.725 (5) |
C12' | 1.0918 (4) | 0.7917 (4) | 1.1612 (8) | 0.0336 (9)* | 0.28 |
H12' | 1.0731 | 0.8229 | 1.1902 | 0.040* | 0.275 (5) |
C13' | 1.1710 (3) | 0.8150 (6) | 1.1748 (5) | 0.068 (5)* | 0.275 (5) |
H13A' | 1.2047 | 0.8182 | 1.2296 | 0.102* | 0.275 (5) |
H13B' | 1.1677 | 0.8618 | 1.1515 | 0.102* | 0.275 (5) |
H13C' | 1.1917 | 0.7802 | 1.1522 | 0.102* | 0.275 (5) |
C14' | 1.0942 (5) | 0.7147 (4) | 1.1852 (4) | 0.043 (3)* | 0.275 (5) |
H14A' | 1.1015 | 0.6836 | 1.1492 | 0.064* | 0.275 (5) |
H14B' | 1.0460 | 0.7025 | 1.1858 | 0.064* | 0.275 (5) |
H14C' | 1.1367 | 0.7080 | 1.2361 | 0.064* | 0.275 (5) |
O1 | 0.94247 (10) | 0.64450 (9) | 1.02783 (11) | 0.0327 (5) | |
H1 | 0.9721 | 0.6071 | 1.0601 | 0.039* | |
C16 | 0.82819 (14) | 0.71965 (13) | 1.00285 (14) | 0.0233 (6) | |
C17 | 0.77945 (15) | 0.75401 (15) | 0.93597 (15) | 0.0295 (6) | |
C18 | 0.75324 (16) | 0.82310 (15) | 0.93266 (16) | 0.0337 (7) | |
C19 | 0.77499 (16) | 0.86147 (15) | 0.99776 (18) | 0.0335 (7) | |
C20 | 0.82436 (16) | 0.83115 (14) | 1.06563 (16) | 0.0297 (7) | |
C21 | 0.84990 (15) | 0.76284 (14) | 1.06632 (15) | 0.0256 (6) | |
C22 | 0.85657 (14) | 0.59546 (13) | 1.08566 (14) | 0.0243 (6) | |
C23 | 0.80485 (15) | 0.60832 (14) | 1.11389 (15) | 0.0281 (6) | |
C24 | 0.80263 (16) | 0.57087 (15) | 1.17254 (15) | 0.0310 (7) | |
C25 | 0.85177 (16) | 0.51507 (14) | 1.20476 (15) | 0.0298 (7) | |
C26 | 0.90341 (16) | 0.49829 (14) | 1.17860 (15) | 0.0295 (7) | |
C27 | 0.90459 (15) | 0.53840 (14) | 1.12137 (15) | 0.0281 (6) | |
C28 | 0.81163 (17) | 0.58405 (14) | 0.94012 (15) | 0.0307 (7) | |
C29 | 0.73233 (19) | 0.58054 (17) | 0.90506 (16) | 0.0403 (8) | |
C30 | 0.6898 (2) | 0.5341 (2) | 0.84715 (18) | 0.0519 (10) | |
C31 | 0.7258 (3) | 0.48501 (18) | 0.82441 (18) | 0.0555 (11) | |
C32 | 0.8037 (2) | 0.48348 (16) | 0.85843 (18) | 0.0490 (10) | |
C33 | 0.84481 (19) | 0.53313 (15) | 0.91387 (16) | 0.0374 (7) | |
C1A | 0.59333 (17) | 0.85308 (17) | −0.01762 (19) | 0.0478 (9) | |
H1A1 | 0.6410 | 0.8413 | 0.0275 | 0.072* | |
H1A2 | 0.5810 | 0.9034 | −0.0159 | 0.072* | |
H1A3 | 0.5995 | 0.8442 | −0.0633 | 0.072* | |
C2A | 0.42191 (17) | 0.70482 (16) | −0.17387 (16) | 0.0391 (8) | |
H2A | 0.3701 | 0.6825 | −0.2007 | 0.047* | |
C3A | 0.4158 (2) | 0.78161 (17) | −0.19937 (17) | 0.0549 (10) | |
H3A1 | 0.3832 | 0.8080 | −0.1827 | 0.082* | |
H3A2 | 0.3935 | 0.7834 | −0.2549 | 0.082* | |
H3A3 | 0.4669 | 0.8031 | −0.1771 | 0.082* | |
C4A | 0.47710 (19) | 0.66245 (18) | −0.19317 (18) | 0.0525 (9) | |
H4A1 | 0.5278 | 0.6845 | −0.1685 | 0.079* | |
H4A2 | 0.4585 | 0.6623 | −0.2483 | 0.079* | |
H4A3 | 0.4803 | 0.6134 | −0.1751 | 0.079* | |
C5A | 0.43756 (15) | 0.64506 (15) | −0.05633 (17) | 0.0328 (7) | |
C6A | 0.39909 (17) | 0.58470 (16) | −0.0982 (2) | 0.0484 (9) | |
H6A | 0.3813 | 0.5900 | −0.1513 | 0.058* | |
C7A | 0.3818 (2) | 0.51926 (19) | −0.0782 (3) | 0.0663 (12) | |
H7A | 0.3548 | 0.4876 | −0.1193 | 0.080* | |
C8A | 0.3977 (2) | 0.4928 (2) | −0.0073 (3) | 0.0780 (15) | |
H8A | 0.3802 | 0.4460 | −0.0053 | 0.094* | |
C9A | 0.4362 (2) | 0.5279 (2) | 0.0598 (3) | 0.0669 (12) | |
H9A | 0.4425 | 0.5017 | 0.1033 | 0.080* | |
C10A | 0.46760 (18) | 0.59520 (18) | 0.0748 (2) | 0.0512 (9) | |
H10A | 0.4918 | 0.6069 | 0.1272 | 0.061* | |
C11A | 0.47108 (16) | 0.65052 (15) | 0.02774 (18) | 0.0358 (7) | |
C12A | 0.5463 (2) | 0.72546 (18) | 0.14084 (18) | 0.0509 (9) | |
H12A | 0.5163 | 0.7042 | 0.1651 | 0.061* | |
C13A | 0.6231 (2) | 0.6913 (2) | 0.1732 (2) | 0.0728 (12) | |
H13D | 0.6176 | 0.6412 | 0.1574 | 0.109* | |
H13E | 0.6471 | 0.6940 | 0.2287 | 0.109* | |
H13F | 0.6552 | 0.7161 | 0.1546 | 0.109* | |
C14A | 0.5545 (2) | 0.80542 (19) | 0.15616 (19) | 0.0639 (11) | |
H14D | 0.5893 | 0.8255 | 0.1382 | 0.096* | |
H14E | 0.5751 | 0.8140 | 0.2108 | 0.096* | |
H14F | 0.5043 | 0.8282 | 0.1293 | 0.096* | |
O2 | 0.41122 (10) | 0.86235 (10) | −0.03770 (10) | 0.0312 (4) | |
H2B | 0.4148 | 0.9038 | −0.0634 | 0.037* | |
C16A | 0.31798 (14) | 0.78511 (14) | −0.01792 (14) | 0.0240 (6) | |
C17A | 0.32803 (15) | 0.74761 (15) | 0.04655 (15) | 0.0282 (6) | |
C18A | 0.30290 (16) | 0.67879 (15) | 0.04564 (16) | 0.0324 (7) | |
C19A | 0.26658 (15) | 0.64271 (14) | −0.02173 (17) | 0.0329 (7) | |
C20A | 0.25722 (15) | 0.67559 (15) | −0.08724 (16) | 0.0315 (7) | |
C21A | 0.28300 (15) | 0.74457 (15) | −0.08379 (15) | 0.0281 (6) | |
C22A | 0.27488 (15) | 0.91480 (14) | −0.09045 (14) | 0.0247 (6) | |
C23A | 0.19674 (15) | 0.90144 (14) | −0.12596 (15) | 0.0267 (6) | |
C24A | 0.14377 (15) | 0.94359 (15) | −0.18290 (15) | 0.0301 (7) | |
C25A | 0.16643 (17) | 1.00371 (14) | −0.20571 (15) | 0.0306 (7) | |
C26A | 0.24251 (17) | 1.02106 (14) | −0.17188 (15) | 0.0303 (7) | |
C27A | 0.29348 (15) | 0.97680 (14) | −0.11649 (15) | 0.0269 (6) | |
C28A | 0.36475 (15) | 0.91514 (14) | 0.05644 (15) | 0.0289 (7) | |
C29A | 0.31556 (17) | 0.91811 (16) | 0.08914 (16) | 0.0362 (7) | |
C30A | 0.3296 (2) | 0.95711 (18) | 0.15283 (17) | 0.0490 (9) | |
C31A | 0.3938 (3) | 0.99832 (18) | 0.18568 (18) | 0.0602 (11) | |
C32A | 0.4425 (2) | 1.00036 (16) | 0.15477 (19) | 0.0535 (10) | |
C33A | 0.42794 (18) | 0.95910 (15) | 0.09173 (17) | 0.0400 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
In1 | 0.02925 (11) | 0.02114 (10) | 0.02950 (11) | 0.00057 (9) | 0.01434 (9) | −0.00002 (8) |
In2 | 0.02644 (11) | 0.02568 (11) | 0.02755 (11) | −0.00003 (9) | 0.01284 (9) | 0.00087 (8) |
N1 | 0.0312 (13) | 0.0253 (12) | 0.0209 (11) | −0.0019 (10) | 0.0115 (10) | −0.0015 (9) |
N2 | 0.0408 (14) | 0.0230 (13) | 0.0226 (12) | 0.0019 (11) | 0.0073 (11) | −0.0002 (10) |
N1A | 0.0307 (13) | 0.0272 (13) | 0.0338 (13) | 0.0008 (11) | 0.0138 (11) | −0.0010 (10) |
N2A | 0.0396 (14) | 0.0381 (14) | 0.0302 (13) | 0.0027 (13) | 0.0174 (12) | 0.0083 (11) |
F17 | 0.0525 (11) | 0.0424 (10) | 0.0246 (9) | 0.0084 (9) | 0.0097 (8) | 0.0004 (7) |
F18 | 0.0567 (12) | 0.0469 (12) | 0.0425 (11) | 0.0206 (9) | 0.0102 (9) | 0.0174 (9) |
F19 | 0.0465 (11) | 0.0255 (9) | 0.0730 (13) | 0.0100 (8) | 0.0335 (10) | 0.0047 (8) |
F20 | 0.0654 (12) | 0.0311 (9) | 0.0468 (11) | −0.0032 (9) | 0.0312 (10) | −0.0130 (8) |
F21 | 0.0460 (10) | 0.0314 (9) | 0.0253 (9) | 0.0013 (8) | 0.0089 (8) | 0.0002 (7) |
F23 | 0.0371 (10) | 0.0463 (11) | 0.0528 (11) | 0.0157 (8) | 0.0290 (9) | 0.0171 (9) |
F24 | 0.0459 (11) | 0.0547 (12) | 0.0496 (11) | 0.0039 (9) | 0.0333 (9) | 0.0056 (9) |
F25 | 0.0565 (12) | 0.0452 (11) | 0.0310 (9) | −0.0037 (9) | 0.0219 (9) | 0.0093 (8) |
F26 | 0.0551 (11) | 0.0364 (10) | 0.0415 (10) | 0.0153 (9) | 0.0221 (9) | 0.0151 (8) |
F27 | 0.0462 (10) | 0.0344 (9) | 0.0434 (10) | 0.0139 (8) | 0.0280 (9) | 0.0085 (8) |
F29 | 0.0365 (10) | 0.0761 (14) | 0.0534 (12) | −0.0148 (10) | 0.0246 (10) | −0.0232 (10) |
F30 | 0.0628 (15) | 0.129 (2) | 0.0537 (13) | −0.0581 (14) | 0.0261 (12) | −0.0366 (13) |
F31 | 0.144 (2) | 0.0671 (14) | 0.0480 (12) | −0.0637 (15) | 0.0517 (14) | −0.0328 (11) |
F32 | 0.148 (2) | 0.0354 (11) | 0.0477 (12) | 0.0111 (12) | 0.0580 (14) | −0.0028 (9) |
F33 | 0.0684 (14) | 0.0500 (12) | 0.0420 (11) | 0.0255 (10) | 0.0286 (10) | −0.0003 (9) |
F17A | 0.0513 (11) | 0.0344 (10) | 0.0249 (9) | −0.0029 (8) | 0.0108 (8) | −0.0001 (7) |
F18A | 0.0677 (13) | 0.0374 (10) | 0.0479 (11) | −0.0026 (9) | 0.0316 (10) | 0.0116 (8) |
F19A | 0.0408 (10) | 0.0251 (9) | 0.0727 (13) | −0.0080 (8) | 0.0269 (10) | −0.0028 (8) |
F20A | 0.0460 (11) | 0.0348 (10) | 0.0455 (11) | −0.0072 (8) | 0.0085 (9) | −0.0170 (8) |
F21A | 0.0443 (10) | 0.0357 (10) | 0.0253 (9) | −0.0015 (8) | 0.0113 (8) | −0.0039 (7) |
F23A | 0.0252 (9) | 0.0355 (9) | 0.0419 (10) | −0.0017 (7) | 0.0130 (8) | 0.0067 (7) |
F24A | 0.0250 (9) | 0.0433 (10) | 0.0413 (10) | 0.0045 (8) | 0.0066 (8) | −0.0001 (8) |
F25A | 0.0467 (11) | 0.0365 (10) | 0.0340 (10) | 0.0145 (8) | 0.0088 (8) | 0.0071 (8) |
F26A | 0.0554 (11) | 0.0309 (10) | 0.0463 (11) | −0.0004 (9) | 0.0235 (9) | 0.0093 (8) |
F27A | 0.0309 (9) | 0.0302 (9) | 0.0463 (10) | −0.0062 (7) | 0.0135 (8) | 0.0021 (7) |
F29A | 0.0380 (10) | 0.0598 (12) | 0.0418 (10) | 0.0067 (9) | 0.0227 (9) | −0.0023 (9) |
F30A | 0.0909 (17) | 0.1073 (19) | 0.0421 (12) | 0.0462 (14) | 0.0345 (12) | −0.0020 (12) |
F31A | 0.135 (2) | 0.0691 (15) | 0.0336 (11) | 0.0341 (15) | 0.0020 (13) | −0.0234 (10) |
F32A | 0.0833 (15) | 0.0439 (12) | 0.0548 (13) | −0.0184 (12) | −0.0224 (12) | −0.0082 (10) |
F33A | 0.0373 (11) | 0.0505 (12) | 0.0585 (12) | −0.0178 (9) | 0.0073 (10) | −0.0028 (9) |
B1 | 0.0249 (17) | 0.0236 (16) | 0.0276 (17) | 0.0025 (14) | 0.0137 (14) | 0.0018 (13) |
B2 | 0.0223 (16) | 0.0272 (17) | 0.0258 (17) | −0.0027 (14) | 0.0096 (14) | −0.0031 (13) |
C1 | 0.047 (2) | 0.041 (2) | 0.075 (2) | 0.0101 (16) | 0.0392 (19) | 0.0031 (17) |
C2 | 0.0405 (17) | 0.0366 (17) | 0.0229 (14) | 0.0045 (15) | 0.0117 (13) | 0.0008 (13) |
C3 | 0.058 (2) | 0.0451 (19) | 0.0314 (17) | −0.0066 (17) | 0.0140 (16) | −0.0118 (15) |
C4 | 0.059 (2) | 0.048 (2) | 0.0282 (17) | 0.0031 (17) | 0.0215 (16) | 0.0034 (14) |
C5 | 0.0251 (15) | 0.0244 (14) | 0.0263 (15) | −0.0032 (12) | 0.0149 (12) | 0.0023 (11) |
C6 | 0.0349 (17) | 0.0331 (17) | 0.0368 (17) | 0.0034 (14) | 0.0186 (14) | 0.0059 (13) |
C7 | 0.0408 (19) | 0.0280 (16) | 0.058 (2) | 0.0087 (15) | 0.0284 (17) | 0.0115 (15) |
C8 | 0.043 (2) | 0.0267 (17) | 0.075 (3) | 0.0031 (15) | 0.036 (2) | −0.0067 (16) |
C9 | 0.0420 (19) | 0.0368 (18) | 0.056 (2) | −0.0056 (16) | 0.0258 (17) | −0.0216 (16) |
C10 | 0.0350 (17) | 0.0339 (17) | 0.0356 (17) | −0.0052 (14) | 0.0165 (14) | −0.0090 (13) |
C11 | 0.0269 (15) | 0.0247 (15) | 0.0274 (15) | −0.0067 (12) | 0.0161 (13) | −0.0016 (11) |
O1 | 0.0291 (11) | 0.0262 (10) | 0.0470 (12) | 0.0052 (9) | 0.0209 (10) | 0.0104 (9) |
C16 | 0.0213 (13) | 0.0234 (14) | 0.0264 (14) | 0.0006 (12) | 0.0120 (12) | 0.0025 (11) |
C17 | 0.0308 (16) | 0.0316 (16) | 0.0274 (16) | −0.0011 (13) | 0.0145 (13) | −0.0003 (12) |
C18 | 0.0294 (16) | 0.0315 (17) | 0.0381 (17) | 0.0072 (13) | 0.0136 (14) | 0.0115 (13) |
C19 | 0.0315 (17) | 0.0220 (15) | 0.056 (2) | 0.0033 (13) | 0.0276 (16) | 0.0041 (14) |
C20 | 0.0340 (17) | 0.0271 (15) | 0.0349 (17) | −0.0040 (13) | 0.0216 (14) | −0.0051 (12) |
C21 | 0.0259 (15) | 0.0246 (14) | 0.0277 (15) | 0.0004 (12) | 0.0135 (13) | 0.0039 (11) |
C22 | 0.0227 (14) | 0.0226 (14) | 0.0247 (14) | −0.0038 (12) | 0.0082 (12) | −0.0030 (11) |
C23 | 0.0234 (15) | 0.0255 (15) | 0.0313 (16) | 0.0012 (12) | 0.0088 (13) | 0.0031 (12) |
C24 | 0.0285 (16) | 0.0386 (17) | 0.0300 (16) | −0.0064 (14) | 0.0170 (13) | −0.0034 (13) |
C25 | 0.0355 (17) | 0.0275 (15) | 0.0229 (15) | −0.0084 (13) | 0.0102 (13) | 0.0013 (12) |
C26 | 0.0332 (17) | 0.0222 (14) | 0.0269 (15) | 0.0011 (12) | 0.0084 (13) | 0.0016 (12) |
C27 | 0.0291 (16) | 0.0244 (15) | 0.0302 (16) | −0.0018 (12) | 0.0132 (13) | −0.0021 (12) |
C28 | 0.0457 (19) | 0.0230 (15) | 0.0272 (15) | −0.0029 (13) | 0.0201 (14) | 0.0011 (12) |
C29 | 0.051 (2) | 0.0424 (19) | 0.0343 (18) | −0.0165 (16) | 0.0255 (16) | −0.0089 (14) |
C30 | 0.059 (2) | 0.065 (2) | 0.0359 (19) | −0.035 (2) | 0.0255 (18) | −0.0132 (17) |
C31 | 0.097 (3) | 0.043 (2) | 0.0337 (19) | −0.037 (2) | 0.037 (2) | −0.0135 (16) |
C32 | 0.102 (3) | 0.0260 (17) | 0.0321 (18) | −0.0001 (19) | 0.042 (2) | −0.0004 (13) |
C33 | 0.056 (2) | 0.0304 (17) | 0.0304 (17) | 0.0027 (15) | 0.0242 (16) | 0.0049 (13) |
C1A | 0.0393 (19) | 0.045 (2) | 0.067 (2) | −0.0088 (16) | 0.0315 (18) | 0.0000 (17) |
C2A | 0.0402 (18) | 0.0375 (18) | 0.0308 (16) | 0.0016 (15) | 0.0087 (14) | −0.0102 (13) |
C3A | 0.080 (3) | 0.052 (2) | 0.0261 (17) | 0.009 (2) | 0.0178 (18) | 0.0044 (15) |
C4A | 0.059 (2) | 0.060 (2) | 0.043 (2) | 0.0105 (19) | 0.0270 (18) | −0.0060 (17) |
C5A | 0.0253 (16) | 0.0251 (15) | 0.0504 (19) | 0.0057 (13) | 0.0195 (15) | 0.0009 (13) |
C6A | 0.0354 (19) | 0.0325 (18) | 0.079 (3) | −0.0014 (15) | 0.0278 (18) | −0.0078 (17) |
C7A | 0.044 (2) | 0.031 (2) | 0.131 (4) | −0.0059 (17) | 0.046 (3) | −0.012 (2) |
C8A | 0.053 (3) | 0.029 (2) | 0.173 (5) | 0.0065 (19) | 0.070 (3) | 0.021 (3) |
C9A | 0.057 (3) | 0.043 (2) | 0.122 (4) | 0.017 (2) | 0.059 (3) | 0.042 (2) |
C10A | 0.048 (2) | 0.045 (2) | 0.073 (2) | 0.0175 (17) | 0.0381 (19) | 0.0258 (18) |
C11A | 0.0286 (16) | 0.0316 (17) | 0.054 (2) | 0.0106 (14) | 0.0250 (15) | 0.0131 (14) |
C12A | 0.057 (2) | 0.055 (2) | 0.0355 (19) | 0.0112 (18) | 0.0163 (17) | 0.0138 (16) |
C13A | 0.065 (3) | 0.097 (3) | 0.051 (2) | 0.034 (2) | 0.022 (2) | 0.012 (2) |
C14A | 0.066 (3) | 0.076 (3) | 0.040 (2) | 0.014 (2) | 0.0160 (19) | −0.0049 (18) |
O2 | 0.0274 (10) | 0.0280 (10) | 0.0425 (12) | 0.0020 (9) | 0.0198 (9) | 0.0039 (9) |
C16A | 0.0171 (13) | 0.0256 (14) | 0.0265 (14) | 0.0009 (12) | 0.0076 (11) | −0.0026 (12) |
C17A | 0.0260 (15) | 0.0284 (15) | 0.0281 (15) | 0.0023 (13) | 0.0104 (13) | −0.0009 (12) |
C18A | 0.0329 (17) | 0.0293 (16) | 0.0374 (17) | 0.0040 (13) | 0.0179 (14) | 0.0059 (13) |
C19A | 0.0237 (15) | 0.0218 (15) | 0.054 (2) | 0.0001 (12) | 0.0185 (15) | −0.0011 (13) |
C20A | 0.0199 (15) | 0.0290 (16) | 0.0368 (17) | −0.0023 (13) | 0.0054 (13) | −0.0102 (13) |
C21A | 0.0240 (15) | 0.0302 (15) | 0.0286 (16) | 0.0038 (13) | 0.0108 (13) | 0.0015 (12) |
C22A | 0.0253 (15) | 0.0254 (14) | 0.0234 (14) | 0.0026 (12) | 0.0110 (12) | −0.0031 (11) |
C23A | 0.0293 (16) | 0.0260 (15) | 0.0273 (15) | 0.0006 (12) | 0.0150 (13) | −0.0008 (11) |
C24A | 0.0247 (16) | 0.0319 (16) | 0.0300 (16) | 0.0037 (13) | 0.0094 (13) | −0.0038 (12) |
C25A | 0.0366 (18) | 0.0269 (15) | 0.0245 (15) | 0.0098 (13) | 0.0106 (14) | −0.0010 (12) |
C26A | 0.0417 (18) | 0.0218 (14) | 0.0311 (16) | 0.0030 (13) | 0.0199 (14) | −0.0003 (12) |
C27A | 0.0270 (15) | 0.0257 (14) | 0.0298 (15) | −0.0003 (12) | 0.0144 (13) | −0.0044 (12) |
C28A | 0.0309 (16) | 0.0211 (14) | 0.0244 (15) | 0.0065 (12) | 0.0038 (13) | 0.0005 (11) |
C29A | 0.0374 (18) | 0.0347 (17) | 0.0281 (16) | 0.0118 (15) | 0.0076 (14) | 0.0016 (13) |
C30A | 0.064 (2) | 0.049 (2) | 0.0278 (17) | 0.0264 (19) | 0.0163 (18) | 0.0020 (15) |
C31A | 0.085 (3) | 0.039 (2) | 0.0259 (18) | 0.024 (2) | 0.000 (2) | −0.0090 (15) |
C32A | 0.059 (2) | 0.0248 (17) | 0.038 (2) | 0.0023 (17) | −0.0109 (18) | −0.0008 (14) |
C33A | 0.0423 (19) | 0.0302 (17) | 0.0326 (17) | 0.0000 (15) | 0.0042 (15) | 0.0030 (13) |
In1—N1 | 2.099 (2) | C5—C11 | 1.491 (3) |
In1—N2 | 2.103 (2) | C6—C7 | 1.385 (4) |
In1—C1 | 2.113 (3) | C7—C8 | 1.390 (4) |
In1—O1 | 2.1938 (17) | C8—C9 | 1.366 (4) |
In2—N2A | 2.098 (2) | C9—C10 | 1.379 (4) |
In2—N1A | 2.101 (2) | C10—C11 | 1.406 (4) |
In2—C1A | 2.113 (3) | C12—C13 | 1.5118 (19) |
In2—O2 | 2.1811 (17) | C12—C14 | 1.5160 (19) |
N1—C5 | 1.340 (3) | C12'—C14' | 1.516 (2) |
N1—C2 | 1.484 (3) | C12'—C13' | 1.518 (2) |
N2—C11 | 1.337 (3) | C16—C17 | 1.389 (3) |
N2—C12 | 1.480 (5) | C16—C21 | 1.389 (4) |
N2—C12' | 1.512 (13) | C17—C18 | 1.386 (4) |
N1A—C5A | 1.341 (3) | C18—C19 | 1.364 (4) |
N1A—C2A | 1.479 (4) | C19—C20 | 1.371 (4) |
N2A—C11A | 1.347 (4) | C20—C21 | 1.375 (4) |
N2A—C12A | 1.480 (4) | C22—C23 | 1.388 (4) |
F17—C17 | 1.354 (3) | C22—C27 | 1.389 (4) |
F18—C18 | 1.352 (3) | C23—C24 | 1.376 (4) |
F19—C19 | 1.345 (3) | C24—C25 | 1.369 (4) |
F20—C20 | 1.343 (3) | C25—C26 | 1.371 (4) |
F21—C21 | 1.349 (3) | C26—C27 | 1.370 (4) |
F23—C23 | 1.357 (3) | C28—C33 | 1.386 (4) |
F24—C24 | 1.344 (3) | C28—C29 | 1.389 (4) |
F25—C25 | 1.351 (3) | C29—C30 | 1.378 (4) |
F26—C26 | 1.347 (3) | C30—C31 | 1.358 (5) |
F27—C27 | 1.366 (3) | C31—C32 | 1.363 (5) |
F29—C29 | 1.352 (3) | C32—C33 | 1.385 (4) |
F30—C30 | 1.354 (4) | C2A—C3A | 1.514 (4) |
F31—C31 | 1.356 (3) | C2A—C4A | 1.528 (4) |
F32—C32 | 1.350 (4) | C5A—C6A | 1.404 (4) |
F33—C33 | 1.355 (3) | C5A—C11A | 1.488 (4) |
F17A—C17A | 1.352 (3) | C6A—C7A | 1.381 (5) |
F18A—C18A | 1.349 (3) | C7A—C8A | 1.383 (6) |
F19A—C19A | 1.348 (3) | C8A—C9A | 1.361 (6) |
F20A—C20A | 1.344 (3) | C9A—C10A | 1.378 (5) |
F21A—C21A | 1.350 (3) | C10A—C11A | 1.418 (4) |
F23A—C23A | 1.355 (3) | C12A—C13A | 1.490 (4) |
F24A—C24A | 1.352 (3) | C12A—C14A | 1.525 (4) |
F25A—C25A | 1.340 (3) | C16A—C21A | 1.391 (3) |
F26A—C26A | 1.347 (3) | C16A—C17A | 1.391 (4) |
F27A—C27A | 1.370 (3) | C17A—C18A | 1.380 (4) |
F29A—C29A | 1.351 (3) | C18A—C19A | 1.370 (4) |
F30A—C30A | 1.358 (4) | C19A—C20A | 1.371 (4) |
F31A—C31A | 1.353 (4) | C20A—C21A | 1.381 (4) |
F32A—C32A | 1.344 (4) | C22A—C23A | 1.390 (4) |
F33A—C33A | 1.354 (4) | C22A—C27A | 1.388 (4) |
B1—O1 | 1.528 (3) | C23A—C24A | 1.382 (4) |
B1—C16 | 1.642 (4) | C24A—C25A | 1.364 (4) |
B1—C28 | 1.648 (4) | C25A—C26A | 1.370 (4) |
B1—C22 | 1.665 (4) | C26A—C27A | 1.376 (4) |
B2—O2 | 1.531 (3) | C28A—C33A | 1.386 (4) |
B2—C16A | 1.640 (4) | C28A—C29A | 1.390 (4) |
B2—C22A | 1.654 (4) | C29A—C30A | 1.373 (4) |
B2—C28A | 1.656 (4) | C30A—C31A | 1.366 (5) |
C2—C3 | 1.522 (4) | C31A—C32A | 1.353 (5) |
C2—C4 | 1.525 (4) | C32A—C33A | 1.383 (4) |
C5—C6 | 1.409 (4) | ||
N1—In1—N2 | 77.96 (8) | F27—C27—C26 | 115.3 (2) |
N1—In1—C1 | 129.58 (11) | F27—C27—C22 | 119.2 (2) |
N2—In1—C1 | 131.59 (12) | C26—C27—C22 | 125.5 (3) |
N1—In1—O1 | 106.05 (8) | C33—C28—C29 | 113.2 (3) |
N2—In1—O1 | 101.37 (8) | C33—C28—B1 | 124.6 (3) |
C1—In1—O1 | 105.45 (10) | C29—C28—B1 | 121.8 (2) |
N2A—In2—N1A | 77.99 (9) | F29—C29—C30 | 116.0 (3) |
N2A—In2—C1A | 129.74 (11) | F29—C29—C28 | 119.8 (3) |
N1A—In2—C1A | 129.81 (11) | C30—C29—C28 | 124.2 (3) |
N2A—In2—O2 | 106.02 (8) | F30—C30—C31 | 120.2 (3) |
N1A—In2—O2 | 103.15 (8) | F30—C30—C29 | 120.1 (3) |
C1A—In2—O2 | 105.68 (10) | C31—C30—C29 | 119.7 (3) |
C5—N1—C2 | 122.5 (2) | F31—C31—C30 | 120.5 (4) |
C5—N1—In1 | 115.45 (16) | F31—C31—C32 | 120.2 (4) |
C2—N1—In1 | 121.64 (17) | C30—C31—C32 | 119.3 (3) |
C11—N2—C12 | 123.1 (2) | F32—C32—C31 | 120.6 (3) |
C11—N2—C12' | 119.3 (4) | F32—C32—C33 | 119.7 (4) |
C12—N2—C12' | 12.1 (3) | C31—C32—C33 | 119.7 (3) |
C11—N2—In1 | 114.85 (17) | F33—C33—C32 | 115.3 (3) |
C12—N2—In1 | 121.96 (19) | F33—C33—C28 | 120.8 (3) |
C12'—N2—In1 | 124.8 (4) | C32—C33—C28 | 123.9 (3) |
C5A—N1A—C2A | 122.5 (2) | N1A—C2A—C3A | 109.2 (2) |
C5A—N1A—In2 | 115.74 (19) | N1A—C2A—C4A | 110.6 (2) |
C2A—N1A—In2 | 121.67 (18) | C3A—C2A—C4A | 111.7 (3) |
C11A—N2A—C12A | 122.7 (3) | N1A—C5A—C6A | 120.7 (3) |
C11A—N2A—In2 | 115.38 (19) | N1A—C5A—C11A | 115.2 (2) |
C12A—N2A—In2 | 121.8 (2) | C6A—C5A—C11A | 124.1 (3) |
O1—B1—C16 | 104.3 (2) | C7A—C6A—C5A | 133.3 (4) |
O1—B1—C28 | 110.8 (2) | C6A—C7A—C8A | 129.8 (4) |
C16—B1—C28 | 115.7 (2) | C9A—C8A—C7A | 125.7 (4) |
O1—B1—C22 | 109.2 (2) | C8A—C9A—C10A | 130.5 (4) |
C16—B1—C22 | 113.0 (2) | C9A—C10A—C11A | 133.0 (4) |
C28—B1—C22 | 103.9 (2) | N2A—C11A—C10A | 120.6 (3) |
O2—B2—C16A | 104.3 (2) | N2A—C11A—C5A | 115.7 (2) |
O2—B2—C22A | 108.5 (2) | C10A—C11A—C5A | 123.7 (3) |
C16A—B2—C22A | 113.6 (2) | N2A—C12A—C13A | 109.9 (3) |
O2—B2—C28A | 110.4 (2) | N2A—C12A—C14A | 109.4 (3) |
C16A—B2—C28A | 115.1 (2) | C13A—C12A—C14A | 110.2 (3) |
C22A—B2—C28A | 104.9 (2) | B2—O2—In2 | 139.92 (16) |
N1—C2—C3 | 109.2 (2) | C21A—C16A—C17A | 112.7 (2) |
N1—C2—C4 | 109.5 (2) | C21A—C16A—B2 | 120.5 (2) |
C3—C2—C4 | 110.7 (3) | C17A—C16A—B2 | 126.8 (2) |
N1—C5—C6 | 121.4 (2) | F17A—C17A—C18A | 115.1 (2) |
N1—C5—C11 | 115.2 (2) | F17A—C17A—C16A | 120.7 (2) |
C6—C5—C11 | 123.4 (2) | C18A—C17A—C16A | 124.2 (3) |
C7—C6—C5 | 133.5 (3) | F18A—C18A—C19A | 119.6 (3) |
C6—C7—C8 | 129.6 (3) | F18A—C18A—C17A | 120.4 (3) |
C9—C8—C7 | 125.3 (3) | C19A—C18A—C17A | 120.0 (3) |
C8—C9—C10 | 130.4 (3) | F19A—C19A—C18A | 120.3 (3) |
C9—C10—C11 | 133.4 (3) | F19A—C19A—C20A | 120.7 (3) |
N2—C11—C10 | 120.6 (2) | C18A—C19A—C20A | 118.9 (3) |
N2—C11—C5 | 115.6 (2) | F20A—C20A—C19A | 120.0 (3) |
C10—C11—C5 | 123.8 (2) | F20A—C20A—C21A | 120.8 (3) |
N2—C12—C13 | 110.6 (3) | C19A—C20A—C21A | 119.2 (3) |
N2—C12—C14 | 110.0 (3) | F21A—C21A—C20A | 115.9 (2) |
C13—C12—C14 | 110.16 (19) | F21A—C21A—C16A | 119.1 (2) |
C14'—C12'—C13' | 109.7 (2) | C20A—C21A—C16A | 124.9 (3) |
C14'—C12'—N2 | 108.4 (7) | C23A—C22A—C27A | 112.4 (2) |
C13'—C12'—N2 | 108.0 (7) | C23A—C22A—B2 | 127.3 (2) |
B1—O1—In1 | 140.47 (16) | C27A—C22A—B2 | 120.2 (2) |
C17—C16—C21 | 112.6 (2) | F23A—C23A—C24A | 115.7 (2) |
C17—C16—B1 | 127.5 (2) | F23A—C23A—C22A | 120.5 (2) |
C21—C16—B1 | 119.8 (2) | C24A—C23A—C22A | 123.8 (3) |
F17—C17—C18 | 115.5 (2) | F24A—C24A—C25A | 119.7 (2) |
F17—C17—C16 | 120.5 (2) | F24A—C24A—C23A | 120.0 (3) |
C18—C17—C16 | 124.0 (3) | C25A—C24A—C23A | 120.4 (3) |
F18—C18—C19 | 119.7 (3) | F25A—C25A—C24A | 120.8 (3) |
F18—C18—C17 | 120.3 (3) | F25A—C25A—C26A | 120.2 (3) |
C19—C18—C17 | 120.0 (3) | C24A—C25A—C26A | 118.9 (3) |
F19—C19—C18 | 120.3 (3) | F26A—C26A—C25A | 120.5 (2) |
F19—C19—C20 | 120.8 (3) | F26A—C26A—C27A | 120.7 (3) |
C18—C19—C20 | 118.9 (3) | C25A—C26A—C27A | 118.8 (3) |
F20—C20—C19 | 120.3 (3) | F27A—C27A—C26A | 115.3 (2) |
F20—C20—C21 | 120.4 (3) | F27A—C27A—C22A | 119.0 (2) |
C19—C20—C21 | 119.3 (3) | C26A—C27A—C22A | 125.6 (3) |
F21—C21—C20 | 115.3 (2) | C33A—C28A—C29A | 113.3 (3) |
F21—C21—C16 | 119.5 (2) | C33A—C28A—B2 | 125.7 (3) |
C20—C21—C16 | 125.1 (2) | C29A—C28A—B2 | 120.7 (2) |
C23—C22—C27 | 112.5 (2) | F29A—C29A—C30A | 117.0 (3) |
C23—C22—B1 | 126.0 (2) | F29A—C29A—C28A | 119.1 (2) |
C27—C22—B1 | 121.4 (2) | C30A—C29A—C28A | 124.0 (3) |
F23—C23—C24 | 115.2 (2) | F30A—C30A—C31A | 120.2 (3) |
F23—C23—C22 | 120.4 (2) | F30A—C30A—C29A | 120.2 (3) |
C24—C23—C22 | 124.3 (3) | C31A—C30A—C29A | 119.6 (3) |
F24—C24—C25 | 119.2 (2) | C32A—C31A—F31A | 120.9 (4) |
F24—C24—C23 | 121.0 (3) | C32A—C31A—C30A | 119.5 (3) |
C25—C24—C23 | 119.8 (3) | F31A—C31A—C30A | 119.6 (4) |
F25—C25—C24 | 120.2 (3) | F32A—C32A—C31A | 120.1 (3) |
F25—C25—C26 | 120.7 (3) | F32A—C32A—C33A | 120.2 (4) |
C24—C25—C26 | 119.1 (3) | C31A—C32A—C33A | 119.7 (3) |
F26—C26—C27 | 121.4 (3) | F33A—C33A—C32A | 115.2 (3) |
F26—C26—C25 | 119.8 (2) | F33A—C33A—C28A | 121.0 (3) |
C27—C26—C25 | 118.8 (3) | C32A—C33A—C28A | 123.8 (3) |
N2—In1—N1—C5 | −4.66 (18) | F29—C29—C30—C31 | −176.3 (3) |
C1—In1—N1—C5 | −139.4 (2) | C28—C29—C30—C31 | 4.1 (5) |
O1—In1—N1—C5 | 93.87 (19) | F30—C30—C31—F31 | −1.3 (5) |
N2—In1—N1—C2 | 168.1 (2) | C29—C30—C31—F31 | 178.9 (3) |
C1—In1—N1—C2 | 33.3 (3) | F30—C30—C31—C32 | 178.5 (3) |
O1—In1—N1—C2 | −93.4 (2) | C29—C30—C31—C32 | −1.3 (5) |
N1—In1—N2—C11 | 8.61 (18) | F31—C31—C32—F32 | −2.5 (5) |
C1—In1—N2—C11 | 141.6 (2) | C30—C31—C32—F32 | 177.6 (3) |
O1—In1—N2—C11 | −95.60 (18) | F31—C31—C32—C33 | 177.9 (3) |
N1—In1—N2—C12 | −168.80 (19) | C30—C31—C32—C33 | −1.9 (5) |
C1—In1—N2—C12 | −35.8 (2) | F32—C32—C33—F33 | 1.8 (4) |
O1—In1—N2—C12 | 86.99 (18) | C31—C32—C33—F33 | −178.7 (3) |
N1—In1—N2—C12' | 177.1 (4) | F32—C32—C33—C28 | −176.9 (3) |
C1—In1—N2—C12' | −49.9 (4) | C31—C32—C33—C28 | 2.6 (5) |
O1—In1—N2—C12' | 72.9 (4) | C29—C28—C33—F33 | −178.7 (2) |
N2A—In2—N1A—C5A | 1.02 (19) | B1—C28—C33—F33 | −6.3 (4) |
C1A—In2—N1A—C5A | 133.4 (2) | C29—C28—C33—C32 | −0.1 (4) |
O2—In2—N1A—C5A | −102.87 (19) | B1—C28—C33—C32 | 172.4 (3) |
N2A—In2—N1A—C2A | −175.8 (2) | C5A—N1A—C2A—C3A | 161.7 (3) |
C1A—In2—N1A—C2A | −43.4 (3) | In2—N1A—C2A—C3A | −21.7 (3) |
O2—In2—N1A—C2A | 80.3 (2) | C5A—N1A—C2A—C4A | −75.0 (3) |
N1A—In2—N2A—C11A | −0.6 (2) | In2—N1A—C2A—C4A | 101.5 (3) |
C1A—In2—N2A—C11A | −133.0 (2) | C2A—N1A—C5A—C6A | −4.3 (4) |
O2—In2—N2A—C11A | 99.9 (2) | In2—N1A—C5A—C6A | 179.0 (2) |
N1A—In2—N2A—C12A | 175.1 (2) | C2A—N1A—C5A—C11A | 175.5 (2) |
C1A—In2—N2A—C12A | 42.7 (3) | In2—N1A—C5A—C11A | −1.3 (3) |
O2—In2—N2A—C12A | −84.5 (2) | N1A—C5A—C6A—C7A | 179.8 (3) |
C5—N1—C2—C3 | −162.2 (3) | C11A—C5A—C6A—C7A | 0.1 (5) |
In1—N1—C2—C3 | 25.6 (3) | C5A—C6A—C7A—C8A | 0.4 (6) |
C5—N1—C2—C4 | 76.4 (3) | C6A—C7A—C8A—C9A | −0.8 (7) |
In1—N1—C2—C4 | −95.8 (2) | C7A—C8A—C9A—C10A | 0.5 (7) |
C2—N1—C5—C6 | 5.5 (4) | C8A—C9A—C10A—C11A | 0.1 (7) |
In1—N1—C5—C6 | 178.12 (19) | C12A—N2A—C11A—C10A | 5.2 (4) |
C2—N1—C5—C11 | −172.2 (2) | In2—N2A—C11A—C10A | −179.2 (2) |
In1—N1—C5—C11 | 0.4 (3) | C12A—N2A—C11A—C5A | −175.5 (3) |
N1—C5—C6—C7 | 177.5 (3) | In2—N2A—C11A—C5A | 0.1 (3) |
C11—C5—C6—C7 | −5.0 (5) | C9A—C10A—C11A—N2A | 179.1 (3) |
C5—C6—C7—C8 | −2.4 (6) | C9A—C10A—C11A—C5A | −0.1 (5) |
C6—C7—C8—C9 | 2.4 (5) | N1A—C5A—C11A—N2A | 0.8 (4) |
C7—C8—C9—C10 | 2.2 (6) | C6A—C5A—C11A—N2A | −179.5 (3) |
C8—C9—C10—C11 | −0.8 (6) | N1A—C5A—C11A—C10A | −179.9 (3) |
C12—N2—C11—C10 | −14.1 (4) | C6A—C5A—C11A—C10A | −0.2 (4) |
C12'—N2—C11—C10 | −0.7 (4) | C11A—N2A—C12A—C13A | 78.0 (4) |
In1—N2—C11—C10 | 168.5 (2) | In2—N2A—C12A—C13A | −97.3 (3) |
C12—N2—C11—C5 | 166.4 (2) | C11A—N2A—C12A—C14A | −160.9 (3) |
C12'—N2—C11—C5 | 179.8 (3) | In2—N2A—C12A—C14A | 23.8 (4) |
In1—N2—C11—C5 | −11.0 (3) | C16A—B2—O2—In2 | −26.9 (3) |
C9—C10—C11—N2 | 173.7 (3) | C22A—B2—O2—In2 | −148.32 (18) |
C9—C10—C11—C5 | −6.8 (5) | C28A—B2—O2—In2 | 97.3 (3) |
N1—C5—C11—N2 | 7.1 (3) | N2A—In2—O2—B2 | −13.1 (3) |
C6—C5—C11—N2 | −170.5 (2) | N1A—In2—O2—B2 | 68.0 (3) |
N1—C5—C11—C10 | −172.4 (3) | C1A—In2—O2—B2 | −153.6 (3) |
C6—C5—C11—C10 | 10.0 (4) | O2—B2—C16A—C21A | −72.3 (3) |
C11—N2—C12—C13 | −139.6 (3) | C22A—B2—C16A—C21A | 45.6 (3) |
C12'—N2—C12—C13 | 145 (2) | C28A—B2—C16A—C21A | 166.6 (2) |
In1—N2—C12—C13 | 37.6 (3) | O2—B2—C16A—C17A | 108.0 (3) |
C11—N2—C12—C14 | 98.5 (4) | C22A—B2—C16A—C17A | −134.0 (3) |
C12'—N2—C12—C14 | 23.3 (18) | C28A—B2—C16A—C17A | −13.1 (4) |
In1—N2—C12—C14 | −84.3 (3) | C21A—C16A—C17A—F17A | 176.3 (2) |
C11—N2—C12'—C14' | 141.5 (5) | B2—C16A—C17A—F17A | −4.0 (4) |
C12—N2—C12'—C14' | −107 (2) | C21A—C16A—C17A—C18A | −3.0 (4) |
In1—N2—C12'—C14' | −26.5 (8) | B2—C16A—C17A—C18A | 176.6 (3) |
C11—N2—C12'—C13' | −99.7 (7) | F17A—C17A—C18A—F18A | 1.1 (4) |
C12—N2—C12'—C13' | 12.1 (17) | C16A—C17A—C18A—F18A | −179.5 (2) |
In1—N2—C12'—C13' | 92.3 (6) | F17A—C17A—C18A—C19A | −178.2 (2) |
C16—B1—O1—In1 | −31.8 (3) | C16A—C17A—C18A—C19A | 1.2 (4) |
C28—B1—O1—In1 | 93.3 (3) | F18A—C18A—C19A—F19A | 0.4 (4) |
C22—B1—O1—In1 | −152.82 (18) | C17A—C18A—C19A—F19A | 179.7 (2) |
N1—In1—O1—B1 | 1.3 (3) | F18A—C18A—C19A—C20A | −178.1 (2) |
N2—In1—O1—B1 | 81.9 (3) | C17A—C18A—C19A—C20A | 1.3 (4) |
C1—In1—O1—B1 | −138.8 (3) | F19A—C19A—C20A—F20A | 0.7 (4) |
O1—B1—C16—C17 | 105.4 (3) | C18A—C19A—C20A—F20A | 179.2 (2) |
C28—B1—C16—C17 | −16.6 (4) | F19A—C19A—C20A—C21A | −179.9 (2) |
C22—B1—C16—C17 | −136.1 (3) | C18A—C19A—C20A—C21A | −1.5 (4) |
O1—B1—C16—C21 | −75.5 (3) | F20A—C20A—C21A—F21A | −1.1 (4) |
C28—B1—C16—C21 | 162.5 (2) | C19A—C20A—C21A—F21A | 179.6 (2) |
C22—B1—C16—C21 | 43.0 (3) | F20A—C20A—C21A—C16A | 178.6 (2) |
C21—C16—C17—F17 | 176.9 (2) | C19A—C20A—C21A—C16A | −0.7 (4) |
B1—C16—C17—F17 | −4.0 (4) | C17A—C16A—C21A—F21A | −177.5 (2) |
C21—C16—C17—C18 | −1.8 (4) | B2—C16A—C21A—F21A | 2.8 (4) |
B1—C16—C17—C18 | 177.3 (3) | C17A—C16A—C21A—C20A | 2.8 (4) |
F17—C17—C18—F18 | 1.2 (4) | B2—C16A—C21A—C20A | −176.9 (2) |
C16—C17—C18—F18 | 180.0 (3) | O2—B2—C22A—C23A | 138.9 (3) |
F17—C17—C18—C19 | −179.0 (3) | C16A—B2—C22A—C23A | 23.4 (4) |
C16—C17—C18—C19 | −0.3 (5) | C28A—B2—C22A—C23A | −103.1 (3) |
F18—C18—C19—F19 | 0.7 (4) | O2—B2—C22A—C27A | −44.2 (3) |
C17—C18—C19—F19 | −179.0 (2) | C16A—B2—C22A—C27A | −159.7 (2) |
F18—C18—C19—C20 | −178.7 (2) | C28A—B2—C22A—C27A | 73.8 (3) |
C17—C18—C19—C20 | 1.6 (4) | C27A—C22A—C23A—F23A | −177.9 (2) |
F19—C19—C20—F20 | 0.5 (4) | B2—C22A—C23A—F23A | −0.8 (4) |
C18—C19—C20—F20 | 179.8 (3) | C27A—C22A—C23A—C24A | 2.4 (4) |
F19—C19—C20—C21 | 179.9 (2) | B2—C22A—C23A—C24A | 179.4 (3) |
C18—C19—C20—C21 | −0.7 (4) | F23A—C23A—C24A—F24A | −2.4 (4) |
F20—C20—C21—F21 | −0.7 (4) | C22A—C23A—C24A—F24A | 177.3 (2) |
C19—C20—C21—F21 | 179.8 (2) | F23A—C23A—C24A—C25A | 177.9 (2) |
F20—C20—C21—C16 | 177.8 (2) | C22A—C23A—C24A—C25A | −2.4 (4) |
C19—C20—C21—C16 | −1.7 (4) | F24A—C24A—C25A—F25A | 0.4 (4) |
C17—C16—C21—F21 | −178.8 (2) | C23A—C24A—C25A—F25A | −179.9 (2) |
B1—C16—C21—F21 | 2.1 (4) | F24A—C24A—C25A—C26A | −178.9 (2) |
C17—C16—C21—C20 | 2.8 (4) | C23A—C24A—C25A—C26A | 0.8 (4) |
B1—C16—C21—C20 | −176.3 (3) | F25A—C25A—C26A—F26A | 1.5 (4) |
O1—B1—C22—C23 | 145.4 (2) | C24A—C25A—C26A—F26A | −179.2 (2) |
C16—B1—C22—C23 | 29.8 (4) | F25A—C25A—C26A—C27A | −178.8 (2) |
C28—B1—C22—C23 | −96.3 (3) | C24A—C25A—C26A—C27A | 0.6 (4) |
O1—B1—C22—C27 | −39.7 (3) | F26A—C26A—C27A—F27A | −1.0 (4) |
C16—B1—C22—C27 | −155.3 (2) | C25A—C26A—C27A—F27A | 179.3 (2) |
C28—B1—C22—C27 | 78.6 (3) | F26A—C26A—C27A—C22A | 179.3 (2) |
C27—C22—C23—F23 | −179.4 (2) | C25A—C26A—C27A—C22A | −0.4 (4) |
B1—C22—C23—F23 | −4.1 (4) | C23A—C22A—C27A—F27A | 179.3 (2) |
C27—C22—C23—C24 | 2.3 (4) | B2—C22A—C27A—F27A | 2.0 (4) |
B1—C22—C23—C24 | 177.6 (3) | C23A—C22A—C27A—C26A | −1.0 (4) |
F23—C23—C24—F24 | −3.1 (4) | B2—C22A—C27A—C26A | −178.3 (3) |
C22—C23—C24—F24 | 175.4 (2) | O2—B2—C28A—C33A | 16.0 (4) |
F23—C23—C24—C25 | 178.9 (2) | C16A—B2—C28A—C33A | 133.7 (3) |
C22—C23—C24—C25 | −2.7 (4) | C22A—B2—C28A—C33A | −100.7 (3) |
F24—C24—C25—F25 | 2.3 (4) | O2—B2—C28A—C29A | −169.8 (2) |
C23—C24—C25—F25 | −179.7 (2) | C16A—B2—C28A—C29A | −52.0 (3) |
F24—C24—C25—C26 | −177.0 (2) | C22A—B2—C28A—C29A | 73.6 (3) |
C23—C24—C25—C26 | 1.1 (4) | C33A—C28A—C29A—F29A | 177.1 (2) |
F25—C25—C26—F26 | 1.9 (4) | B2—C28A—C29A—F29A | 2.1 (4) |
C24—C25—C26—F26 | −178.9 (2) | C33A—C28A—C29A—C30A | −3.7 (4) |
F25—C25—C26—C27 | −178.7 (2) | B2—C28A—C29A—C30A | −178.7 (3) |
C24—C25—C26—C27 | 0.6 (4) | F29A—C29A—C30A—F30A | 3.6 (4) |
F26—C26—C27—F27 | −1.0 (4) | C28A—C29A—C30A—F30A | −175.6 (3) |
C25—C26—C27—F27 | 179.5 (2) | F29A—C29A—C30A—C31A | −178.0 (3) |
F26—C26—C27—C22 | 178.6 (2) | C28A—C29A—C30A—C31A | 2.8 (5) |
C25—C26—C27—C22 | −0.9 (4) | F30A—C30A—C31A—C32A | 178.7 (3) |
C23—C22—C27—F27 | 179.1 (2) | C29A—C30A—C31A—C32A | 0.3 (5) |
B1—C22—C27—F27 | 3.6 (4) | F30A—C30A—C31A—F31A | −2.1 (5) |
C23—C22—C27—C26 | −0.5 (4) | C29A—C30A—C31A—F31A | 179.5 (3) |
B1—C22—C27—C26 | −176.0 (3) | F31A—C31A—C32A—F32A | −1.8 (5) |
O1—B1—C28—C33 | 22.1 (4) | C30A—C31A—C32A—F32A | 177.4 (3) |
C16—B1—C28—C33 | 140.5 (3) | F31A—C31A—C32A—C33A | 178.8 (3) |
C22—B1—C28—C33 | −95.1 (3) | C30A—C31A—C32A—C33A | −1.9 (5) |
O1—B1—C28—C29 | −166.1 (2) | F32A—C32A—C33A—F33A | 1.4 (4) |
C16—B1—C28—C29 | −47.7 (4) | C31A—C32A—C33A—F33A | −179.2 (3) |
C22—B1—C28—C29 | 76.7 (3) | F32A—C32A—C33A—C28A | −178.6 (3) |
C33—C28—C29—F29 | 177.1 (2) | C31A—C32A—C33A—C28A | 0.7 (5) |
B1—C28—C29—F29 | 4.4 (4) | C29A—C28A—C33A—F33A | −178.1 (2) |
C33—C28—C29—C30 | −3.3 (4) | B2—C28A—C33A—F33A | −3.4 (4) |
B1—C28—C29—C30 | −176.0 (3) | C29A—C28A—C33A—C32A | 2.0 (4) |
F29—C29—C30—F30 | 3.9 (4) | B2—C28A—C33A—C32A | 176.6 (3) |
C28—C29—C30—F30 | −175.7 (3) |
Experimental details
Crystal data | |
Chemical formula | [In(CH3)(C18HBF15O)(C13H19N2)] |
Mr | 862.15 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 183 |
a, b, c (Å) | 19.6683 (16), 18.7739 (16), 19.8049 (17) |
β (°) | 117.201 (1) |
V (Å3) | 6504.2 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.84 |
Crystal size (mm) | 0.43 × 0.40 × 0.36 |
Data collection | |
Diffractometer | Bruker CCD-1000 area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Blessing, 1995) |
Tmin, Tmax | 0.713, 0.751 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 41003, 13220, 9101 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.075, 0.97 |
No. of reflections | 13220 |
No. of parameters | 947 |
No. of restraints | 12 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.68, −0.68 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXTL.
In1—N1 | 2.099 (2) | In2—N1A | 2.101 (2) |
In1—N2 | 2.103 (2) | In2—C1A | 2.113 (3) |
In1—C1 | 2.113 (3) | In2—O2 | 2.1811 (17) |
In1—O1 | 2.1938 (17) | B1—O1 | 1.528 (3) |
In2—N2A | 2.098 (2) | B2—O2 | 1.531 (3) |
N1—In1—N2 | 77.96 (8) | N2A—In2—C1A | 129.74 (11) |
N1—In1—C1 | 129.58 (11) | N1A—In2—C1A | 129.81 (11) |
N2—In1—C1 | 131.59 (12) | N2A—In2—O2 | 106.02 (8) |
N1—In1—O1 | 106.05 (8) | N1A—In2—O2 | 103.15 (8) |
N2—In1—O1 | 101.37 (8) | C1A—In2—O2 | 105.68 (10) |
C1—In1—O1 | 105.45 (10) | B1—O1—In1 | 140.47 (16) |
N2A—In2—N1A | 77.99 (9) | B2—O2—In2 | 139.92 (16) |
Cationic group 13 complexes have been investigated because of their potential applications as catalysts for olefin polymerization, alkyne oligomerization and other reactions, and as general Lewis-acid catalysts (Bochmann & Dawson, 1996; Coles & Jordan, 1997; Atwood, 1998; Korolev et al., 1999; Radzewich et al., 1999; Dagorne et al., 2000). In the course of our studies of cationic indium complexes containing N,N'-diisopropylaminotroponiminate (iPr2—ATI) ligands (Delpech et al., 2000), we isolated and structurally characterized the title compound, (I).
The molecular structure of (I) consists of an ion pair in which the {iPr2—ATI}In(Me)+ cation is associated with the B(C6F5)3(OH)− anion through an In—O(H)—B bridge. The asymmetric unit of (I) contains two independent molecules with statistically equivalent metrical parameters but different conformations. The molecules differ in the positions of the methyl substituents of the isopropyl groups at atoms N2 and N2A, and in the conformation of the In—O(H)—B(C6F5)3 unit. The latter difference is best illustrated by the torsion angles for the two molecules: B1—O1—In1—C8 42.3 (3)° and B2—O2—In2—C8A 27.8 (3)°. In the following discussion, the bond lengths and angles of (I) are reported as average values for the two molecules.
The In atom possesses a severely distorted tetrahedral geometry. The N—In—N bite angle [77.92 (6)°] is in the expected range for iPr2—ATI complexes (Korolev et al., 1999; Ihara et al., 1998). The O—In—N [average 104 (2)°] and O—In—C angles [average 105.6 (2)°] are similar, while the C—In—N angles are larger [average 130 (1)°]. The In—C [2.114 (3) Å] and In—N [2.103 (6) Å] bond lengths, and the N—In—N bite angle in (I) are similar to those in the closely related complex [{iPr2—ATI}In(Me)(NMe2Ph)]+ [In—C 2.121 (2) Å; In—N(ATI) average 2.108 (4) Å; N—In—N 78.18 (6)°; Delpech et al., 2000]. The In—O bond length [2.186 (9) Å] in (I) is similar to the In—µ-OH distances in [{InC(SiMe3)3}4(µ4-O)(µ-OH)6] [2.17 (2) Å; Al-Juaid et al., 1986].
The five- and seven-membered ring of the {IPr2—ATI}In units are planar to within 0.08 Å in the In1 molecule and to within 0.01 Å in the In2 molecule. The isopropyl groups adopt orientations that minimize steric interactions with the closest H atoms on the seven-membered rings; consequently, the methyl groups point toward the In centre. The isopropyl group on atom N2 (but not N2A in the second molecule) is disordered over two positions in a 72/28 ratio and was refined isotropically with an idealized geometry. The C—N bond distances in the InN2C2 chelate ring of (I) [average 1.339 (6) Å] are intermediate between the normal Csp2—N single-bond (1.47 Å) and C═N double-bond distances (1.27 Å), which is consistent with significant delocalization of the π-electrons within the ATI unit, as observed in related compounds (Ihara et al., 1998; Korolev et al., 1999).
The [B(C6F5)3(OH)]− anion exhibits a slightly distorted tetrahedral geometry. The B—O bond distance [1.532 (4) Å] is similar to the B—O bond lengths in related compounds, e.g.[(C5Me5)2Ta(OH)Me][B(C6F5)3OH] [1.490 (10) Å; Schaefer et al., 1993], V{OB(C6F5)3}(acac)2 [1.527 (2) Å], MoO{OB(C6F5)3}(acac)2 [1.521 (3) Å], Ti{OB(C6F5)3}(acac)2 [1.496 (3) Å; Galsworthy et al., 1997], and the aqua adduct B(C6F5)3(H2O)-dioxane [1.565 (3) Å; Janiak et al., 1998].