organic compounds
1-Hydroxypiperidinium 16-hydroxy-6,6-pentamethylene-11,13,19-triphenyl-19-(1-piperidiniumoxy)-8,10,12,14,15,17,18,20-octaoxa-6-azonia-11,13,16-tribora-7,9,19-triboratatrispiro[5.0.1.5.3.3]icosane diethyl ether hemisolvate, C33H49B6N3O11·0.5C4H10O, contains a tetracyclic ring system, with two boroxine, a BOBON, and a piperidinium ring spiro-fused; the diethyl ether solvent molecule is disordered over an inversion centre.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680200380X/om6081sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680200380X/om6081IIsup2.hkl |
CCDC reference: 183788
Computing details top
Data collection: D*TREK (Molecular Structure Corporation, 1997); cell refinement: D*TREK; data reduction: TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.
(II) top
Crystal data top
C5H12NO+·C28H37B6N2O10−·0.5C4H10O | Z = 2 |
Mr = 765.68 | F(000) = 814 |
Triclinic, P1 | Dx = 1.226 Mg m−3 |
a = 10.636 (2) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 15.340 (2) Å | Cell parameters from 9653 reflections |
c = 15.545 (2) Å | θ = 2.3–27.9° |
α = 105.467 (2)° | µ = 0.09 mm−1 |
β = 107.949 (4)° | T = 173 K |
γ = 109.453 (2)° | Chip, colorless |
V = 2073.3 (5) Å3 | 0.40 × 0.30 × 0.20 mm |
Data collection top
Quantum CCD diffractometer | 8500 independent reflections |
Radiation source: X-ray tube | 5491 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.038 |
CCD scans | θmax = 27.9°, θmin = 2.3° |
Absorption correction: multi-scan d*TREK (Molecular Structure Corporation, 1997) | h = −12→13 |
Tmin = 0.96, Tmax = 0.98 | k = −19→17 |
19307 measured reflections | l = −20→18 |
Refinement top
Refinement on F2 | 2 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.102 | Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo2)] |
S = 1.41 | (Δ/σ)max = 0.036 |
8500 reflections | Δρmax = 0.49 e Å−3 |
527 parameters | Δρmin = −0.49 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | −0.0879 (1) | 0.66068 (7) | 0.68249 (6) | 0.0194 (2) | |
O2 | −0.0982 (1) | 0.55593 (7) | 0.77181 (7) | 0.0231 (3) | |
O3 | 0.1269 (1) | 0.63697 (7) | 0.76185 (6) | 0.0189 (2) | |
O4 | 0.1590 (1) | 0.77887 (6) | 0.72005 (6) | 0.0171 (2) | |
O5 | 0.1453 (1) | 0.74887 (7) | 0.55634 (6) | 0.0290 (3) | |
O6 | 0.0380 (1) | 0.60865 (6) | 0.59149 (6) | 0.0202 (2) | |
O7 | 0.3276 (1) | 0.90565 (6) | 0.69225 (6) | 0.0176 (2) | |
O8 | 0.1628 (1) | 0.95341 (7) | 0.59987 (7) | 0.0278 (3) | |
O9 | 0.3822 (1) | 0.97103 (7) | 0.57224 (6) | 0.0281 (3) | |
O10 | 0.0598 (1) | 0.58618 (8) | 0.44014 (7) | 0.0351 (3) | |
O11 | 0.5066 (1) | 0.93379 (7) | 0.86520 (7) | 0.0315 (3) | |
O12 | 1.0000 | 1.0000 | 1.0000 | 0.0953 (9) | |
N1 | 0.0808 (1) | 0.88197 (9) | 0.63036 (8) | 0.0253 (3) | |
N2 | 0.3244 (1) | 0.86917 (8) | 0.50256 (8) | 0.0217 (3) | |
N3 | 0.4239 (1) | 0.83355 (8) | 0.85447 (8) | 0.0211 (3) | |
C1 | −0.0709 (2) | 0.8169 (1) | 0.5477 (1) | 0.0469 (5) | |
C2 | −0.1631 (2) | 0.8770 (2) | 0.5360 (2) | 0.0813 (7) | |
C3 | −0.1666 (3) | 0.9289 (2) | 0.6330 (2) | 0.0829 (8) | |
C4 | −0.0114 (2) | 0.9976 (2) | 0.7093 (2) | 0.0638 (7) | |
C5 | 0.0753 (2) | 0.9380 (1) | 0.7228 (1) | 0.0348 (5) | |
C6 | 0.2447 (2) | 0.8589 (1) | 0.40064 (9) | 0.0270 (4) | |
C7 | 0.1817 (2) | 0.7499 (1) | 0.3279 (1) | 0.0325 (4) | |
C8 | 0.3017 (2) | 0.7165 (1) | 0.3346 (1) | 0.0348 (4) | |
C9 | 0.3876 (2) | 0.7327 (1) | 0.4404 (1) | 0.0324 (4) | |
C10 | 0.4482 (2) | 0.8420 (1) | 0.5118 (1) | 0.0297 (4) | |
C11 | −0.3313 (2) | 0.5700 (1) | 0.6890 (1) | 0.0226 (4) | |
C12 | −0.4116 (2) | 0.6008 (1) | 0.6245 (1) | 0.0305 (4) | |
C13 | −0.5615 (2) | 0.5704 (1) | 0.5967 (1) | 0.0393 (5) | |
C14 | −0.6348 (2) | 0.5081 (1) | 0.6330 (1) | 0.0410 (5) | |
C15 | −0.5595 (2) | 0.4763 (1) | 0.6963 (1) | 0.0420 (5) | |
C16 | −0.4092 (2) | 0.5070 (1) | 0.7245 (1) | 0.0327 (5) | |
C17 | 0.1155 (2) | 0.5202 (1) | 0.85116 (9) | 0.0191 (3) | |
C18 | 0.0461 (2) | 0.4690 (1) | 0.8983 (1) | 0.0259 (4) | |
C19 | 0.1084 (2) | 0.4206 (1) | 0.9495 (1) | 0.0343 (4) | |
C20 | 0.2395 (2) | 0.4213 (1) | 0.9535 (1) | 0.0390 (5) | |
C21 | 0.3097 (2) | 0.4700 (1) | 0.9067 (1) | 0.0377 (5) | |
C22 | 0.2482 (2) | 0.5192 (1) | 0.8565 (1) | 0.0282 (4) | |
C23 | 0.4291 (2) | 1.0954 (1) | 0.73009 (9) | 0.0196 (3) | |
C24 | 0.5754 (2) | 1.1257 (1) | 0.7946 (1) | 0.0289 (4) | |
C25 | 0.6664 (2) | 1.2242 (1) | 0.8673 (1) | 0.0402 (4) | |
C26 | 0.6144 (2) | 1.2953 (1) | 0.8766 (1) | 0.0442 (4) | |
C27 | 0.4717 (2) | 1.2683 (1) | 0.8136 (1) | 0.0403 (5) | |
C28 | 0.3802 (2) | 1.1695 (1) | 0.7409 (1) | 0.0277 (4) | |
C29 | 0.4366 (2) | 0.8381 (1) | 0.9535 (1) | 0.0274 (4) | |
C30 | 0.5919 (2) | 0.8637 (1) | 1.0215 (1) | 0.0369 (4) | |
C31 | 0.6393 (2) | 0.7879 (1) | 0.9754 (1) | 0.0491 (5) | |
C32 | 0.6288 (2) | 0.7857 (1) | 0.8749 (1) | 0.0456 (5) | |
C33 | 0.4750 (2) | 0.7631 (1) | 0.8071 (1) | 0.0307 (4) | |
C34 | 0.9342 (5) | 1.0770 (5) | 0.9740 (4) | 0.092 (2) | 0.500 |
C35 | 0.9394 (4) | 1.1391 (3) | 1.0490 (3) | 0.130 (1) | |
C36 | 1.0100 (6) | 0.9432 (5) | 0.9389 (5) | 0.105 (2) | 0.500 |
B1 | −0.1643 (2) | 0.5989 (1) | 0.7150 (1) | 0.0193 (4) | |
B2 | 0.0468 (2) | 0.5745 (1) | 0.7922 (1) | 0.0173 (4) | |
B3 | 0.0575 (2) | 0.6723 (1) | 0.6893 (1) | 0.0171 (4) | |
B4 | 0.1826 (2) | 0.8220 (1) | 0.6529 (1) | 0.0184 (4) | |
B5 | 0.0795 (2) | 0.6459 (1) | 0.5298 (1) | 0.0217 (4) | |
B6 | 0.3248 (2) | 0.9794 (1) | 0.6504 (1) | 0.0198 (4) | |
H1 | −0.0629 | 0.7910 | 0.4858 | 0.056* | |
H2 | −0.1219 | 0.7596 | 0.5613 | 0.056* | |
H3 | −0.1191 | 0.9285 | 0.5139 | 0.097* | |
H4 | −0.2650 | 0.8297 | 0.4859 | 0.097* | |
H5 | −0.2216 | 0.9683 | 0.6235 | 0.100* | |
H6 | −0.2145 | 0.8778 | 0.6542 | 0.100* | |
H7 | 0.0355 | 1.0492 | 0.6880 | 0.077* | |
H8 | −0.0117 | 1.0308 | 0.7724 | 0.077* | |
H9 | 0.0295 | 0.8885 | 0.7464 | 0.042* | |
H10 | 0.1772 | 0.9852 | 0.7728 | 0.042* | |
H11 | 0.1639 | 0.8772 | 0.3972 | 0.032* | |
H12 | 0.3137 | 0.9041 | 0.3839 | 0.032* | |
H13 | 0.1085 | 0.7058 | 0.3428 | 0.039* | |
H14 | 0.1333 | 0.7441 | 0.2604 | 0.039* | |
H15 | 0.2563 | 0.6444 | 0.2910 | 0.042* | |
H16 | 0.3699 | 0.7562 | 0.3137 | 0.042* | |
H17 | 0.3215 | 0.6878 | 0.4590 | 0.039* | |
H18 | 0.4702 | 0.7164 | 0.4443 | 0.039* | |
H19 | 0.5189 | 0.8869 | 0.4959 | 0.035* | |
H20 | 0.4983 | 0.8499 | 0.5799 | 0.035* | |
H21 | −0.3606 | 0.6450 | 0.5983 | 0.036* | |
H22 | −0.6152 | 0.5930 | 0.5513 | 0.047* | |
H23 | −0.7407 | 0.4866 | 0.6136 | 0.049* | |
H24 | −0.6119 | 0.4318 | 0.7217 | 0.050* | |
H25 | −0.3566 | 0.4840 | 0.7701 | 0.039* | |
H26 | −0.0481 | 0.4672 | 0.8953 | 0.031* | |
H27 | 0.0583 | 0.3859 | 0.9827 | 0.041* | |
H28 | 0.2831 | 0.3872 | 0.9896 | 0.047* | |
H29 | 0.4029 | 0.4701 | 0.9088 | 0.045* | |
H30 | 0.2994 | 0.5540 | 0.8238 | 0.034* | |
H31 | 0.6151 | 1.0763 | 0.7885 | 0.035* | |
H32 | 0.7682 | 1.2428 | 0.9121 | 0.048* | |
H33 | 0.6785 | 1.3647 | 0.9277 | 0.053* | |
H34 | 0.4337 | 1.3186 | 0.8195 | 0.048* | |
H35 | 0.2788 | 1.1518 | 0.6964 | 0.033* | |
H36 | 0.4103 | 0.8902 | 0.9832 | 0.033* | |
H37 | 0.3681 | 0.7720 | 0.9457 | 0.033* | |
H38 | 0.6598 | 0.9318 | 1.0331 | 0.044* | |
H39 | 0.5952 | 0.8623 | 1.0848 | 0.044* | |
H40 | 0.7420 | 0.8075 | 1.0192 | 0.059* | |
H41 | 0.5746 | 0.7204 | 0.9668 | 0.059* | |
H42 | 0.6995 | 0.8518 | 0.8844 | 0.055* | |
H43 | 0.6533 | 0.7330 | 0.8442 | 0.055* | |
H44 | 0.4064 | 0.6934 | 0.7906 | 0.037* | |
H45 | 0.4753 | 0.7700 | 0.7463 | 0.037* | |
H46 | 0.320 (2) | 0.811 (1) | 0.810 (1) | 0.025 (4)* | |
H47 | 0.435 (2) | 0.929 (2) | 0.792 (2) | 0.088 (7)* | |
H48 | 0.257 (2) | 0.824 (1) | 0.518 (1) | 0.031 (4)* | |
H49 | 0.029 (2) | 0.524 (2) | 0.434 (1) | 0.066 (6)* | |
H50 | 0.9908 | 1.1152 | 0.9462 | 0.109* | 0.500 |
H51 | 0.8295 | 1.0360 | 0.9239 | 0.109* | 0.500 |
H52 | 1.0408 | 1.1807 | 1.0986 | 0.156* | 0.500 |
H53 | 0.8972 | 1.1830 | 1.0280 | 0.156* | 0.500 |
H54 | 0.8789 | 1.1018 | 1.0758 | 0.156* | 0.500 |
H55 | 0.9159 | 0.9050 | 0.8849 | 0.136* | 0.500 |
H56 | 1.0849 | 0.9851 | 0.9248 | 0.136* | 0.500 |
H57 | 1.0103 | 1.1896 | 1.0382 | 0.156* | 0.500 |
H58 | 0.9312 | 1.1723 | 1.1088 | 0.156* | 0.500 |
H59 | 0.8405 | 1.1077 | 0.9913 | 0.156* | 0.500 |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0194 (5) | 0.0194 (5) | 0.0248 (5) | 0.0088 (4) | 0.0115 (4) | 0.0144 (4) |
O2 | 0.0229 (5) | 0.0262 (5) | 0.0324 (5) | 0.0129 (4) | 0.0170 (4) | 0.0211 (4) |
O3 | 0.0186 (5) | 0.0172 (5) | 0.0244 (5) | 0.0075 (4) | 0.0101 (4) | 0.0132 (4) |
O4 | 0.0215 (5) | 0.0102 (4) | 0.0169 (4) | 0.0034 (4) | 0.0087 (4) | 0.0062 (3) |
O5 | 0.0472 (7) | 0.0098 (5) | 0.0215 (5) | 0.0011 (4) | 0.0192 (4) | 0.0046 (4) |
O6 | 0.0268 (6) | 0.0105 (4) | 0.0209 (4) | 0.0033 (4) | 0.0133 (4) | 0.0065 (4) |
O7 | 0.0197 (5) | 0.0106 (4) | 0.0213 (4) | 0.0043 (4) | 0.0085 (4) | 0.0087 (4) |
O8 | 0.0235 (5) | 0.0195 (5) | 0.0322 (5) | 0.0024 (4) | 0.0034 (4) | 0.0187 (4) |
O9 | 0.0425 (7) | 0.0084 (4) | 0.0235 (5) | 0.0002 (4) | 0.0179 (4) | 0.0033 (4) |
O10 | 0.0609 (8) | 0.0113 (5) | 0.0289 (5) | 0.0038 (5) | 0.0298 (5) | 0.0063 (4) |
O11 | 0.0329 (6) | 0.0176 (5) | 0.0298 (5) | 0.0027 (5) | 0.0040 (5) | 0.0124 (4) |
O12 | 0.065 (2) | 0.098 (2) | 0.076 (2) | 0.013 (1) | 0.015 (1) | 0.020 (1) |
N1 | 0.0185 (6) | 0.0190 (6) | 0.0307 (6) | 0.0024 (5) | 0.0038 (5) | 0.0154 (5) |
N2 | 0.0299 (7) | 0.0092 (5) | 0.0190 (5) | 0.0017 (5) | 0.0114 (5) | 0.0043 (4) |
N3 | 0.0204 (7) | 0.0163 (6) | 0.0217 (5) | 0.0047 (5) | 0.0061 (5) | 0.0090 (5) |
C1 | 0.0234 (9) | 0.038 (1) | 0.052 (1) | −0.0047 (7) | −0.0066 (7) | 0.0294 (8) |
C2 | 0.020 (1) | 0.073 (2) | 0.131 (2) | 0.004 (1) | −0.008 (1) | 0.084 (1) |
C3 | 0.048 (1) | 0.073 (2) | 0.164 (2) | 0.042 (1) | 0.047 (1) | 0.079 (2) |
C4 | 0.047 (1) | 0.044 (1) | 0.131 (2) | 0.0333 (9) | 0.050 (1) | 0.050 (1) |
C5 | 0.037 (1) | 0.0294 (9) | 0.0525 (9) | 0.0210 (8) | 0.0283 (8) | 0.0195 (7) |
C6 | 0.0361 (9) | 0.0183 (7) | 0.0216 (6) | 0.0084 (7) | 0.0092 (6) | 0.0100 (6) |
C7 | 0.043 (1) | 0.0198 (7) | 0.0216 (7) | 0.0058 (7) | 0.0101 (7) | 0.0060 (6) |
C8 | 0.049 (1) | 0.0180 (7) | 0.0365 (8) | 0.0078 (7) | 0.0280 (7) | 0.0082 (6) |
C9 | 0.037 (1) | 0.0235 (8) | 0.0469 (8) | 0.0146 (7) | 0.0261 (7) | 0.0190 (7) |
C10 | 0.0279 (9) | 0.0251 (8) | 0.0318 (8) | 0.0070 (7) | 0.0112 (6) | 0.0141 (6) |
C11 | 0.0256 (8) | 0.0214 (7) | 0.0274 (7) | 0.0126 (6) | 0.0168 (6) | 0.0108 (6) |
C12 | 0.0292 (8) | 0.0383 (9) | 0.0350 (8) | 0.0186 (7) | 0.0181 (7) | 0.0215 (7) |
C13 | 0.0297 (9) | 0.054 (1) | 0.0427 (9) | 0.0256 (9) | 0.0141 (7) | 0.0249 (8) |
C14 | 0.0227 (9) | 0.047 (1) | 0.055 (1) | 0.0169 (8) | 0.0198 (8) | 0.0181 (8) |
C15 | 0.0331 (9) | 0.047 (1) | 0.070 (1) | 0.0227 (8) | 0.0366 (9) | 0.0359 (9) |
C16 | 0.0319 (9) | 0.0380 (9) | 0.0512 (9) | 0.0224 (8) | 0.0283 (8) | 0.0301 (8) |
C17 | 0.0230 (7) | 0.0126 (6) | 0.0167 (6) | 0.0054 (6) | 0.0066 (5) | 0.0049 (5) |
C18 | 0.0262 (8) | 0.0215 (7) | 0.0244 (7) | 0.0056 (6) | 0.0079 (6) | 0.0119 (6) |
C19 | 0.044 (1) | 0.0266 (8) | 0.0315 (8) | 0.0117 (7) | 0.0124 (7) | 0.0205 (7) |
C20 | 0.049 (1) | 0.0309 (9) | 0.0383 (8) | 0.0239 (8) | 0.0091 (8) | 0.0207 (7) |
C21 | 0.043 (1) | 0.043 (1) | 0.0433 (9) | 0.0313 (9) | 0.0196 (8) | 0.0239 (8) |
C22 | 0.0326 (9) | 0.0280 (8) | 0.0313 (8) | 0.0172 (7) | 0.0158 (7) | 0.0156 (6) |
C23 | 0.0259 (8) | 0.0135 (6) | 0.0166 (6) | 0.0035 (6) | 0.0101 (5) | 0.0082 (5) |
C24 | 0.0279 (8) | 0.0208 (7) | 0.0294 (7) | 0.0025 (6) | 0.0093 (6) | 0.0130 (6) |
C25 | 0.034 (1) | 0.0318 (9) | 0.0244 (7) | −0.0084 (7) | 0.0024 (6) | 0.0109 (6) |
C26 | 0.063 (1) | 0.0174 (8) | 0.0235 (8) | −0.0065 (8) | 0.0176 (7) | 0.0006 (6) |
C27 | 0.068 (1) | 0.0165 (7) | 0.0425 (9) | 0.0161 (8) | 0.0342 (8) | 0.0123 (7) |
C28 | 0.0381 (9) | 0.0171 (7) | 0.0280 (7) | 0.0098 (6) | 0.0161 (6) | 0.0108 (6) |
C29 | 0.0312 (8) | 0.0269 (8) | 0.0223 (7) | 0.0092 (7) | 0.0122 (6) | 0.0118 (6) |
C30 | 0.0323 (9) | 0.0372 (9) | 0.0275 (8) | 0.0049 (7) | 0.0034 (6) | 0.0193 (7) |
C31 | 0.028 (1) | 0.048 (1) | 0.065 (1) | 0.0172 (9) | 0.0061 (8) | 0.0327 (9) |
C32 | 0.0321 (9) | 0.042 (1) | 0.066 (1) | 0.0212 (9) | 0.0242 (8) | 0.0179 (9) |
C33 | 0.0340 (9) | 0.0249 (8) | 0.0335 (8) | 0.0138 (7) | 0.0175 (7) | 0.0083 (6) |
C34 | 0.035 (2) | 0.142 (4) | 0.089 (3) | 0.008 (3) | 0.013 (2) | 0.091 (3) |
C35 | 0.087 (2) | 0.134 (3) | 0.144 (3) | 0.042 (2) | 0.039 (2) | 0.044 (3) |
C36 | 0.032 (3) | 0.088 (4) | 0.143 (6) | 0.004 (3) | 0.044 (3) | −0.001 (3) |
B1 | 0.0251 (8) | 0.0171 (8) | 0.0187 (7) | 0.0106 (7) | 0.0117 (6) | 0.0080 (6) |
B2 | 0.0210 (8) | 0.0131 (7) | 0.0163 (7) | 0.0062 (6) | 0.0088 (6) | 0.0051 (6) |
B3 | 0.0197 (8) | 0.0135 (7) | 0.0181 (7) | 0.0053 (6) | 0.0091 (6) | 0.0081 (6) |
B4 | 0.0224 (8) | 0.0117 (7) | 0.0183 (7) | 0.0046 (6) | 0.0087 (6) | 0.0064 (5) |
B5 | 0.0259 (9) | 0.0122 (7) | 0.0225 (7) | 0.0026 (7) | 0.0124 (7) | 0.0066 (6) |
B6 | 0.0240 (8) | 0.0125 (7) | 0.0187 (7) | 0.0045 (6) | 0.0074 (6) | 0.0078 (5) |
Geometric parameters (Å, º) top
O1—B1 | 1.345 (2) | C11—C16 | 1.399 (2) |
O1—B3 | 1.464 (2) | C11—B1 | 1.567 (2) |
O2—B1 | 1.394 (2) | C12—C13 | 1.385 (2) |
O2—B2 | 1.385 (2) | C12—H21 | 0.98 |
O3—B2 | 1.347 (2) | C13—C14 | 1.380 (3) |
O3—B3 | 1.480 (2) | C13—H22 | 0.98 |
O4—B3 | 1.468 (2) | C14—C15 | 1.370 (3) |
O4—B4 | 1.418 (2) | C14—H23 | 0.98 |
O5—B4 | 1.452 (2) | C15—C16 | 1.388 (3) |
O5—B5 | 1.376 (2) | C15—H24 | 0.98 |
O6—B3 | 1.479 (2) | C16—H25 | 0.98 |
O6—B5 | 1.352 (2) | C17—C18 | 1.397 (2) |
O7—B4 | 1.443 (2) | C17—C22 | 1.393 (2) |
O7—B6 | 1.451 (2) | C17—B2 | 1.571 (2) |
O8—N1 | 1.443 (2) | C18—C19 | 1.394 (2) |
O8—B6 | 1.512 (2) | C18—H26 | 0.98 |
O9—N2 | 1.428 (2) | C19—C20 | 1.372 (3) |
O9—B6 | 1.514 (2) | C19—H27 | 0.98 |
O10—B5 | 1.355 (2) | C20—C21 | 1.379 (3) |
O10—H49 | 0.87 (3) | C20—H28 | 0.98 |
O11—N3 | 1.428 (2) | C21—C22 | 1.391 (3) |
O11—H47 | 1.12 (3) | C21—H29 | 0.98 |
O12—C34 | 1.636 (8) | C22—H30 | 0.98 |
O12—C36 | 1.16 (1) | C23—C24 | 1.397 (2) |
N1—C1 | 1.488 (2) | C23—C28 | 1.391 (2) |
N1—C5 | 1.494 (2) | C23—B6 | 1.611 (2) |
N1—B4 | 1.656 (2) | C24—C25 | 1.392 (2) |
N2—C6 | 1.484 (2) | C24—H31 | 0.98 |
N2—C10 | 1.486 (2) | C25—C26 | 1.372 (3) |
N2—H48 | 0.96 (2) | C25—H32 | 0.98 |
N3—C29 | 1.484 (2) | C26—C27 | 1.373 (3) |
N3—C33 | 1.490 (2) | C26—H33 | 0.98 |
N3—H46 | 0.98 (2) | C27—C28 | 1.395 (2) |
C1—C2 | 1.558 (4) | C27—H34 | 0.98 |
C1—H1 | 0.98 | C28—H35 | 0.98 |
C1—H2 | 0.98 | C29—C30 | 1.506 (3) |
C2—C3 | 1.524 (4) | C29—H36 | 0.98 |
C2—H3 | 0.98 | C29—H37 | 0.98 |
C2—H4 | 0.98 | C30—C31 | 1.513 (3) |
C3—C4 | 1.487 (4) | C30—H38 | 0.98 |
C3—H5 | 0.98 | C30—H39 | 0.98 |
C3—H6 | 0.98 | C31—C32 | 1.521 (3) |
C4—C5 | 1.508 (3) | C31—H40 | 0.98 |
C4—H7 | 0.98 | C31—H41 | 0.98 |
C4—H8 | 0.98 | C32—C33 | 1.507 (3) |
C5—H9 | 0.98 | C32—H42 | 0.98 |
C5—H10 | 0.98 | C32—H43 | 0.98 |
C6—C7 | 1.517 (2) | C33—H44 | 0.98 |
C6—H11 | 0.98 | C33—H45 | 0.98 |
C6—H12 | 0.98 | C34—C35 | 1.267 (8) |
C7—C8 | 1.512 (3) | C34—H50 | 0.98 |
C7—H13 | 0.98 | C34—H51 | 0.99 |
C7—H14 | 0.98 | C35—C36i | 1.56 (1) |
C8—C9 | 1.518 (3) | C35—H52 | 0.96 |
C8—H15 | 0.98 | C35—H53 | 0.99 |
C8—H16 | 0.98 | C35—H54 | 0.98 |
C9—C10 | 1.519 (2) | C35—H57 | 0.98 |
C9—H17 | 0.98 | C35—H58 | 0.98 |
C9—H18 | 0.98 | C35—H59 | 1.00 |
C10—H19 | 0.98 | C36—H55 | 0.94 |
C10—H20 | 0.98 | C36—H56 | 0.97 |
C11—C12 | 1.397 (2) | ||
O3···N3 | 3.111 (2) | O10···B3ii | 3.497 (2) |
O3···C33 | 3.293 (2) | O10···B5ii | 3.590 (2) |
O3···O10ii | 3.379 (2) | O11···C24 | 3.346 (2) |
O3···C29 | 3.395 (2) | O11···B4 | 3.427 (2) |
O4···N3 | 2.621 (2) | O11···C29iii | 3.582 (2) |
O4···O11 | 3.249 (2) | N3···B4 | 3.299 (2) |
O4···C33 | 3.332 (2) | N3···B3 | 3.452 (2) |
O4···C29 | 3.545 (2) | C3···C10iv | 3.518 (3) |
O6···O10ii | 2.662 (2) | C7···C18ii | 3.541 (2) |
O6···O6ii | 3.404 (2) | C8···C25v | 3.574 (2) |
O6···B5ii | 3.426 (2) | C12···C13vi | 3.589 (3) |
O7···O11 | 2.592 (2) | C13···C33iv | 3.590 (3) |
O7···N3 | 3.046 (2) | C18···C18vii | 3.577 (3) |
O10···B2ii | 3.358 (2) | C25···C29iii | 3.531 (2) |
B1—O1—B3 | 122.1 (1) | C19—C18—H26 | 119.4 |
B1—O2—B2 | 119.4 (1) | C18—C19—C20 | 120.2 (2) |
B2—O3—B3 | 121.8 (1) | C18—C19—H27 | 119.9 |
B3—O4—B4 | 123.9 (1) | C20—C19—H27 | 119.9 |
B4—O5—B5 | 122.4 (1) | C19—C20—C21 | 119.9 (2) |
B3—O6—B5 | 124.0 (1) | C19—C20—H28 | 120.1 |
B4—O7—B6 | 112.2 (1) | C21—C20—H28 | 120.0 |
N1—O8—B6 | 108.3 (1) | C20—C21—C22 | 119.8 (2) |
N2—O9—B6 | 113.5 (1) | C20—C21—H29 | 120.1 |
B5—O10—H49 | 109 (1) | C22—C21—H29 | 120.1 |
N3—O11—H47 | 99 (1) | C17—C22—C21 | 121.8 (2) |
C34—O12—C36 | 119.9 (5) | C17—C22—H30 | 119.1 |
O8—N1—C1 | 107.8 (1) | C21—C22—H30 | 119.1 |
O8—N1—C5 | 109.7 (1) | C24—C23—C28 | 116.5 (1) |
O8—N1—B4 | 102.4 (1) | C24—C23—B6 | 120.3 (2) |
C1—N1—C5 | 111.1 (2) | C28—C23—B6 | 123.2 (2) |
C1—N1—B4 | 114.7 (1) | C23—C24—C25 | 121.8 (2) |
C5—N1—B4 | 110.8 (1) | C23—C24—H31 | 119.1 |
O9—N2—C6 | 109.9 (1) | C25—C24—H31 | 119.1 |
O9—N2—C10 | 109.0 (1) | C24—C25—C26 | 120.3 (2) |
O9—N2—H48 | 109 (1) | C24—C25—H32 | 119.8 |
C6—N2—C10 | 111.7 (1) | C26—C25—H32 | 119.9 |
C6—N2—H48 | 109 (1) | C25—C26—C27 | 119.3 (2) |
C10—N2—H48 | 108 (1) | C25—C26—H33 | 120.4 |
O11—N3—C29 | 108.3 (1) | C27—C26—H33 | 120.3 |
O11—N3—C33 | 110.5 (1) | C26—C27—C28 | 120.4 (2) |
O11—N3—H46 | 107 (1) | C26—C27—H34 | 119.9 |
C29—N3—C33 | 113.1 (1) | C28—C27—H34 | 119.7 |
C29—N3—H46 | 109.6 (9) | C23—C28—C27 | 121.7 (2) |
C33—N3—H46 | 108 (1) | C23—C28—H35 | 119.2 |
N1—C1—C2 | 111.6 (2) | C27—C28—H35 | 119.1 |
N1—C1—H1 | 108.9 | N3—C29—C30 | 111.3 (1) |
N1—C1—H2 | 108.9 | N3—C29—H36 | 109.0 |
C2—C1—H1 | 109.0 | N3—C29—H37 | 109.1 |
C2—C1—H2 | 109.0 | C30—C29—H36 | 109.0 |
H1—C1—H2 | 109.3 | C30—C29—H37 | 109.0 |
C1—C2—C3 | 112.0 (2) | H36—C29—H37 | 109.4 |
C1—C2—H3 | 108.8 | C29—C30—C31 | 110.4 (2) |
C1—C2—H4 | 108.7 | C29—C30—H38 | 109.2 |
C3—C2—H3 | 109.0 | C29—C30—H39 | 109.2 |
C3—C2—H4 | 108.9 | C31—C30—H38 | 109.2 |
H3—C2—H4 | 109.4 | C31—C30—H39 | 109.3 |
C2—C3—C4 | 108.3 (2) | H38—C30—H39 | 109.5 |
C2—C3—H5 | 109.6 | C30—C31—C32 | 110.2 (2) |
C2—C3—H6 | 109.7 | C30—C31—H40 | 109.3 |
C4—C3—H5 | 109.8 | C30—C31—H41 | 109.3 |
C4—C3—H6 | 109.8 | C32—C31—H40 | 109.3 |
H5—C3—H6 | 109.7 | C32—C31—H41 | 109.4 |
C3—C4—C5 | 110.2 (2) | H40—C31—H41 | 109.4 |
C3—C4—H7 | 109.4 | C31—C32—C33 | 111.2 (2) |
C3—C4—H8 | 109.3 | C31—C32—H42 | 109.1 |
C5—C4—H7 | 109.3 | C31—C32—H43 | 109.1 |
C5—C4—H8 | 109.3 | C33—C32—H42 | 109.0 |
H7—C4—H8 | 109.4 | C33—C32—H43 | 109.0 |
N1—C5—C4 | 114.1 (2) | H42—C32—H43 | 109.5 |
N1—C5—H9 | 108.3 | N3—C33—C32 | 111.8 (1) |
N1—C5—H10 | 108.2 | N3—C33—H44 | 108.9 |
C4—C5—H9 | 108.3 | N3—C33—H45 | 108.9 |
C4—C5—H10 | 108.4 | C32—C33—H44 | 108.9 |
H9—C5—H10 | 109.4 | C32—C33—H45 | 108.9 |
N2—C6—C7 | 109.2 (1) | H44—C33—H45 | 109.5 |
N2—C6—H11 | 109.5 | O12—C34—C35 | 113.0 (4) |
N2—C6—H12 | 109.6 | O12—C34—H50 | 109.3 |
C7—C6—H11 | 109.6 | O12—C34—H51 | 108.5 |
C7—C6—H12 | 109.6 | C35—C34—H50 | 108.6 |
H11—C6—H12 | 109.4 | C35—C34—H51 | 108.4 |
C6—C7—C8 | 111.4 (1) | H50—C34—H51 | 108.9 |
C6—C7—H13 | 109.0 | C34—C35—H52 | 110.0 |
C6—C7—H14 | 109.0 | C34—C35—H53 | 108.8 |
C8—C7—H13 | 109.0 | C34—C35—H54 | 109.6 |
C8—C7—H14 | 109.0 | C36i—C35—H57 | 110.6 |
H13—C7—H14 | 109.4 | C36i—C35—H58 | 109.3 |
C7—C8—C9 | 110.5 (1) | C36i—C35—H59 | 110.6 |
C7—C8—H15 | 109.3 | H52—C35—H53 | 109.5 |
C7—C8—H16 | 109.2 | H52—C35—H54 | 110.7 |
C9—C8—H15 | 109.2 | H53—C35—H54 | 108.2 |
C9—C8—H16 | 109.1 | H57—C35—H58 | 109.8 |
H15—C8—H16 | 109.5 | H57—C35—H59 | 108.3 |
C8—C9—C10 | 110.8 (1) | H58—C35—H59 | 108.2 |
C8—C9—H17 | 109.1 | O12—C36—C35i | 125.5 (8) |
C8—C9—H18 | 109.1 | O12—C36—H55 | 107.1 |
C10—C9—H17 | 109.2 | O12—C36—H56 | 105.1 |
C10—C9—H18 | 109.1 | C35i—C36—H55 | 103.0 |
H17—C9—H18 | 109.5 | C35i—C36—H56 | 102.2 |
N2—C10—C9 | 109.6 (1) | H55—C36—H56 | 114.3 |
N2—C10—H19 | 109.4 | O1—B1—O2 | 121.1 (2) |
N2—C10—H20 | 109.4 | O1—B1—C11 | 121.8 (2) |
C9—C10—H19 | 109.5 | O2—B1—C11 | 117.1 (1) |
C9—C10—H20 | 109.4 | O2—B2—O3 | 121.0 (2) |
H19—C10—H20 | 109.5 | O2—B2—C17 | 118.4 (1) |
C12—C11—C16 | 117.0 (2) | O3—B2—C17 | 120.6 (2) |
C12—C11—B1 | 121.5 (1) | O1—B3—O3 | 111.7 (1) |
C16—C11—B1 | 121.4 (2) | O1—B3—O4 | 111.1 (1) |
C11—C12—C13 | 121.7 (2) | O1—B3—O6 | 108.6 (1) |
C11—C12—H21 | 119.2 | O3—B3—O4 | 107.8 (1) |
C13—C12—H21 | 119.1 | O3—B3—O6 | 107.1 (1) |
C12—C13—C14 | 119.8 (2) | O4—B3—O6 | 110.5 (1) |
C12—C13—H22 | 120.1 | O4—B4—O5 | 114.3 (1) |
C14—C13—H22 | 120.2 | O4—B4—O7 | 114.5 (1) |
C13—C14—C15 | 120.1 (2) | O4—B4—N1 | 111.5 (1) |
C13—C14—H23 | 120.0 | O5—B4—O7 | 110.7 (1) |
C15—C14—H23 | 120.0 | O5—B4—N1 | 105.4 (1) |
C14—C15—C16 | 120.2 (2) | O7—B4—N1 | 99.0 (1) |
C14—C15—H24 | 119.9 | O5—B5—O6 | 120.4 (1) |
C16—C15—H24 | 119.9 | O5—B5—O10 | 116.4 (1) |
C11—C16—C15 | 121.3 (2) | O6—B5—O10 | 123.1 (1) |
C11—C16—H25 | 119.4 | O7—B6—O8 | 105.1 (1) |
C15—C16—H25 | 119.3 | O7—B6—O9 | 112.8 (1) |
C18—C17—C22 | 117.0 (2) | O7—B6—C23 | 113.8 (1) |
C18—C17—B2 | 122.2 (2) | O8—B6—O9 | 107.6 (1) |
C22—C17—B2 | 120.8 (1) | O8—B6—C23 | 114.1 (1) |
C17—C18—C19 | 121.3 (2) | O9—B6—C23 | 103.5 (1) |
C17—C18—H26 | 119.3 | ||
O1—B1—O2—B2 | −2.2 (2) | N1—O8—B6—C23 | −113.5 (1) |
O1—B1—C11—C12 | 5.1 (2) | N1—C1—C2—C3 | −53.6 (3) |
O1—B1—C11—C16 | −178.9 (2) | N1—C5—C4—C3 | 58.7 (3) |
O1—B3—O3—B2 | 19.0 (2) | N1—B4—O4—B3 | 97.4 (2) |
O1—B3—O4—B4 | −95.1 (2) | N1—B4—O5—B5 | −117.0 (2) |
O1—B3—O6—B5 | 108.1 (2) | N1—B4—O7—B6 | −29.9 (1) |
O2—B1—O1—B3 | 11.0 (2) | N2—O9—B6—C23 | 169.0 (1) |
O2—B1—C11—C12 | −173.6 (1) | N2—C6—C7—C8 | −57.0 (2) |
O2—B1—C11—C16 | 2.3 (2) | N2—C10—C9—C8 | 56.8 (2) |
O2—B2—O3—B3 | −12.4 (2) | N3—C29—C30—C31 | −56.6 (2) |
O2—B2—C17—C18 | −11.6 (2) | N3—C33—C32—C31 | 53.2 (2) |
O2—B2—C17—C22 | 166.9 (1) | C1—N1—O8—B6 | −150.2 (1) |
O3—B2—O2—B1 | 3.0 (2) | C1—N1—C5—C4 | −53.2 (2) |
O3—B2—C17—C18 | 168.9 (1) | C1—C2—C3—C4 | 57.7 (3) |
O3—B2—C17—C22 | −12.6 (2) | C2—C1—N1—C5 | 49.4 (2) |
O3—B3—O1—B1 | −18.3 (2) | C2—C1—N1—B4 | 176.0 (2) |
O3—B3—O4—B4 | 142.2 (1) | C2—C3—C4—C5 | −59.1 (3) |
O3—B3—O6—B5 | −131.2 (2) | C4—C5—N1—B4 | 178.1 (2) |
O4—B3—O1—B1 | −138.7 (1) | C5—N1—O8—B6 | 88.8 (2) |
O4—B3—O3—B2 | 141.3 (1) | C6—N2—O9—B6 | 120.9 (1) |
O4—B3—O6—B5 | −14.0 (2) | C6—N2—C10—C9 | −60.2 (2) |
O4—B4—O5—B5 | 5.9 (2) | C6—C7—C8—C9 | 55.0 (2) |
O4—B4—O7—B6 | −148.6 (1) | C7—C6—N2—C10 | 59.9 (2) |
O4—B4—N1—O8 | 156.2 (1) | C7—C8—C9—C10 | −54.7 (2) |
O4—B4—N1—C1 | −87.4 (2) | C10—N2—O9—B6 | −116.4 (1) |
O4—B4—N1—C5 | 39.3 (2) | C11—C12—C13—C14 | 0.0 (3) |
O5—B4—O4—B3 | −22.1 (2) | C11—C16—C15—C14 | −0.4 (3) |
O5—B4—O7—B6 | 80.4 (2) | C11—B1—O1—B3 | −167.7 (1) |
O5—B4—N1—O8 | −79.2 (1) | C11—B1—O2—B2 | 176.5 (1) |
O5—B4—N1—C1 | 37.2 (2) | C12—C11—C16—C15 | 0.2 (3) |
O5—B4—N1—C5 | 163.9 (1) | C12—C13—C14—C15 | −0.1 (3) |
O5—B5—O6—B3 | 0.4 (3) | C13—C12—C11—C16 | −0.1 (3) |
O6—B3—O1—B1 | 99.6 (2) | C13—C12—C11—B1 | 176.0 (2) |
O6—B3—O3—B2 | −99.8 (2) | C13—C14—C15—C16 | 0.3 (3) |
O6—B3—O4—B4 | 25.4 (2) | C15—C16—C11—B1 | −175.9 (2) |
O6—B5—O5—B4 | 4.4 (3) | C17—C18—C19—C20 | −0.9 (3) |
O7—B4—O4—B3 | −151.2 (1) | C17—C22—C21—C20 | −0.5 (3) |
O7—B4—O5—B5 | 136.9 (2) | C17—B2—O2—B1 | −176.5 (1) |
O7—B4—N1—O8 | 35.2 (1) | C17—B2—O3—B3 | 167.1 (1) |
O7—B4—N1—C1 | 151.6 (1) | C18—C17—C22—C21 | −0.3 (2) |
O7—B4—N1—C5 | −81.6 (1) | C18—C19—C20—C21 | 0.0 (3) |
O7—B6—O8—N1 | 11.9 (2) | C19—C18—C17—C22 | 1.0 (2) |
O7—B6—O9—N2 | 45.6 (2) | C19—C18—C17—B2 | 179.5 (1) |
O7—B6—C23—C24 | 48.2 (2) | C19—C20—C21—C22 | 0.7 (3) |
O7—B6—C23—C28 | −130.1 (2) | C21—C22—C17—B2 | −178.8 (2) |
O8—N1—C1—C2 | −70.7 (2) | C23—C24—C25—C26 | −1.0 (3) |
O8—N1—C5—C4 | 65.8 (2) | C23—C28—C27—C26 | 0.3 (3) |
O8—B6—O7—B4 | 14.0 (2) | C23—B6—O7—B4 | 139.5 (1) |
O8—B6—O9—N2 | −69.9 (2) | C24—C23—C28—C27 | −1.1 (2) |
O8—B6—C23—C24 | 168.8 (1) | C24—C25—C26—C27 | 0.2 (3) |
O8—B6—C23—C28 | −9.4 (2) | C25—C24—C23—C28 | 1.4 (2) |
O9—N2—C6—C7 | −179.0 (1) | C25—C24—C23—B6 | −177.0 (1) |
O9—N2—C10—C9 | 178.2 (1) | C25—C26—C27—C28 | 0.2 (3) |
O9—B6—O7—B4 | −103.0 (1) | C27—C28—C23—B6 | 177.2 (1) |
O9—B6—O8—N1 | 132.3 (1) | C29—N3—C33—C32 | −52.7 (2) |
O9—B6—C23—C24 | −74.6 (2) | C29—C30—C31—C32 | 57.5 (2) |
O9—B6—C23—C28 | 107.1 (2) | C30—C29—N3—C33 | 54.4 (2) |
O10—B5—O5—B4 | −175.6 (2) | C30—C31—C32—C33 | −56.0 (2) |
O10—B5—O6—B3 | −179.6 (2) | C34—O12—C36—C35i | −175.7 (4) |
O11—N3—C29—C30 | −68.5 (2) | C35—C34—O12—C36 | −175.3 (5) |
O11—N3—C33—C32 | 69.0 (2) | B4—N1—O8—B6 | −28.9 (1) |
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+2, −z+2; (iv) x−1, y, z; (v) −x+1, −y+2, −z+1; (vi) −x−1, −y+1, −z+1; (vii) −x, −y+1, −z+2. |