Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105041089/sf1024sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270105041089/sf1024Isup2.hkl |
CCDC reference: 299632
Boric acid (H3BO3, 3.09 g, 0.05 mol) was dissolved in excess dimethylaminopropanol (25.8 g, 0.25 mol) in a rotary evaporator at 353 K and 40 mm H g vacuum, with strong bubbling due to the removal of water. When the bubbling subsided, the temperature was raised to 413 K to remove excess solvent, leaving a yellow liquid, which solidified when cooled to ambient temperature. The solid, which was very hydroscopic, was recrystallized from a benzene/pentane mixture (1:1, 30 ml) to afford white long-platelet crystals (yield 6 g, 93%). 1H NMR in CDCl3 showed the absence of hydroxy H atoms.
All H atoms were constrained to their expected geometries (C—H = 0.99 and 0.98 Å) and refined as riding with Uiso(H) values of 1.2 or 1.5 times Ueq(C).
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001) and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997).
C15H36B3N3O6 | F(000) = 5040 |
Mr = 386.90 | Dx = 1.239 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2628 reflections |
a = 10.333 (2) Å | θ = 2.6–21.8° |
b = 28.914 (5) Å | µ = 0.09 mm−1 |
c = 41.642 (8) Å | T = 113 K |
V = 12441 (4) Å3 | Plate, colourless |
Z = 8 | 0.67 × 0.65 × 0.09 mm |
Bruker SMART CCD area-detector diffractometer | 12733 independent reflections |
Radiation source: fine-focus sealed tube | 5839 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.277 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.4°, θmin = 2.0° |
ϕ and ω scans | h = −12→12 |
Absorption correction: multi-scan (Blessing, 1995) | k = −36→36 |
Tmin = 0.855, Tmax = 1.0 | l = −51→49 |
105164 measured reflections |
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)] = 0.070 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0516P)2] where P = (Fo2 + 2Fc2)/3 |
12733 reflections | (Δ/σ)max = 0.001 |
748 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C15H36B3N3O6 | V = 12441 (4) Å3 |
Mr = 386.90 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.333 (2) Å | µ = 0.09 mm−1 |
b = 28.914 (5) Å | T = 113 K |
c = 41.642 (8) Å | 0.67 × 0.65 × 0.09 mm |
Bruker SMART CCD area-detector diffractometer | 12733 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 5839 reflections with I > 2σ(I) |
Tmin = 0.855, Tmax = 1.0 | Rint = 0.277 |
105164 measured reflections |
R[F2 > 2σ(F2)] = 0.070 | 0 restraints |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.26 e Å−3 |
12733 reflections | Δρmin = −0.28 e Å−3 |
748 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 | ||
O1 | 0.45176 (19) | 0.17499 (7) | 0.16602 (5) | 0.0185 (5) | |
O2 | 0.47200 (19) | 0.09273 (7) | 0.16964 (5) | 0.0180 (5) | |
O3 | 0.56150 (18) | 0.14112 (7) | 0.21186 (5) | 0.0169 (5) | |
O4 | 0.3883 (2) | 0.13082 (8) | 0.12277 (5) | 0.0279 (6) | |
O5 | 0.6156 (2) | 0.06231 (7) | 0.21057 (5) | 0.0200 (5) | |
O6 | 0.46497 (19) | 0.21741 (7) | 0.21431 (5) | 0.0191 (5) | |
N1 | 0.3048 (3) | 0.04199 (9) | 0.03962 (6) | 0.0249 (7) | |
N2 | 0.3894 (2) | 0.08281 (9) | 0.22608 (6) | 0.0190 (6) | |
N3 | 0.6664 (2) | 0.20624 (9) | 0.18286 (6) | 0.0164 (6) | |
B1 | 0.4392 (3) | 0.13181 (14) | 0.15349 (10) | 0.0202 (9) | |
B2 | 0.5205 (4) | 0.09716 (13) | 0.20262 (9) | 0.0175 (9) | |
B3 | 0.5260 (4) | 0.18219 (13) | 0.19490 (9) | 0.0182 (9) | |
C1 | 0.3873 (4) | 0.09038 (11) | 0.10278 (8) | 0.0283 (9) | |
H1A | 0.3012 | 0.0754 | 0.1034 | 0.034* | |
H1B | 0.4527 | 0.0679 | 0.1103 | 0.034* | |
C2 | 0.4185 (3) | 0.10602 (12) | 0.06887 (8) | 0.0274 (9) | |
H2A | 0.3521 | 0.1287 | 0.0621 | 0.033* | |
H2B | 0.5028 | 0.1223 | 0.0692 | 0.033* | |
C3 | 0.4248 (3) | 0.06787 (12) | 0.04396 (8) | 0.0305 (9) | |
H3A | 0.4496 | 0.0817 | 0.0231 | 0.037* | |
H3B | 0.4940 | 0.0459 | 0.0502 | 0.037* | |
C4 | 0.1986 (3) | 0.07153 (13) | 0.02921 (8) | 0.0352 (10) | |
H4A | 0.1819 | 0.0951 | 0.0456 | 0.053* | |
H4B | 0.1206 | 0.0527 | 0.0261 | 0.053* | |
H4C | 0.2217 | 0.0866 | 0.0089 | 0.053* | |
C5 | 0.3249 (4) | 0.00630 (13) | 0.01510 (9) | 0.0389 (10) | |
H5A | 0.2444 | −0.0110 | 0.0119 | 0.058* | |
H5B | 0.3932 | −0.0149 | 0.0222 | 0.058* | |
H5C | 0.3507 | 0.0209 | −0.0051 | 0.058* | |
C6 | 0.5807 (3) | 0.01586 (11) | 0.20361 (8) | 0.0249 (8) | |
H6A | 0.6552 | −0.0047 | 0.2081 | 0.030* | |
H6B | 0.5592 | 0.0131 | 0.1805 | 0.030* | |
C7 | 0.4653 (3) | 0.00041 (12) | 0.22354 (8) | 0.0274 (9) | |
H7A | 0.4387 | −0.0310 | 0.2168 | 0.033* | |
H7B | 0.4904 | −0.0009 | 0.2465 | 0.033* | |
C8 | 0.3525 (3) | 0.03334 (11) | 0.21955 (8) | 0.0273 (9) | |
H8A | 0.3188 | 0.0308 | 0.1974 | 0.033* | |
H8B | 0.2822 | 0.0242 | 0.2344 | 0.033* | |
C9 | 0.4224 (3) | 0.08906 (12) | 0.26062 (7) | 0.0228 (8) | |
H9A | 0.4444 | 0.1215 | 0.2646 | 0.034* | |
H9B | 0.4966 | 0.0695 | 0.2661 | 0.034* | |
H9C | 0.3480 | 0.0803 | 0.2739 | 0.034* | |
C10 | 0.2770 (3) | 0.11327 (12) | 0.21935 (8) | 0.0249 (9) | |
H10A | 0.2080 | 0.1069 | 0.2349 | 0.037* | |
H10B | 0.2451 | 0.1073 | 0.1976 | 0.037* | |
H10C | 0.3036 | 0.1457 | 0.2212 | 0.037* | |
C11 | 0.5345 (3) | 0.22941 (11) | 0.24270 (7) | 0.0213 (8) | |
H11A | 0.5468 | 0.2014 | 0.2561 | 0.026* | |
H11B | 0.4834 | 0.2520 | 0.2553 | 0.026* | |
C12 | 0.6658 (3) | 0.25021 (12) | 0.23464 (8) | 0.0230 (8) | |
H12A | 0.6530 | 0.2809 | 0.2245 | 0.028* | |
H12B | 0.7154 | 0.2549 | 0.2547 | 0.028* | |
C13 | 0.7432 (3) | 0.21966 (11) | 0.21211 (7) | 0.0209 (8) | |
H13A | 0.8224 | 0.2363 | 0.2053 | 0.025* | |
H13B | 0.7702 | 0.1913 | 0.2237 | 0.025* | |
C14 | 0.6416 (3) | 0.24733 (11) | 0.16210 (8) | 0.0231 (8) | |
H14A | 0.7243 | 0.2614 | 0.1559 | 0.035* | |
H14B | 0.5898 | 0.2700 | 0.1740 | 0.035* | |
H14C | 0.5946 | 0.2377 | 0.1428 | 0.035* | |
C15 | 0.7446 (3) | 0.17300 (11) | 0.16390 (8) | 0.0244 (8) | |
H15A | 0.6960 | 0.1636 | 0.1448 | 0.037* | |
H15B | 0.7636 | 0.1457 | 0.1770 | 0.037* | |
H15C | 0.8258 | 0.1877 | 0.1573 | 0.037* | |
O11 | 0.45504 (19) | 0.21219 (7) | 0.83060 (5) | 0.0178 (5) | |
O12 | 0.4715 (2) | 0.12966 (7) | 0.83332 (5) | 0.0191 (5) | |
O13 | 0.56521 (19) | 0.17665 (7) | 0.87579 (5) | 0.0171 (5) | |
O14 | 0.3921 (2) | 0.16798 (7) | 0.78684 (5) | 0.0238 (6) | |
O15 | 0.62124 (19) | 0.09790 (7) | 0.87196 (5) | 0.0189 (5) | |
O16 | 0.46340 (19) | 0.25215 (7) | 0.88013 (5) | 0.0196 (5) | |
N11 | 0.4716 (3) | 0.07893 (10) | 0.70755 (7) | 0.0300 (7) | |
N12 | 0.3964 (2) | 0.11682 (9) | 0.88998 (6) | 0.0184 (6) | |
N13 | 0.6663 (2) | 0.24430 (9) | 0.84843 (6) | 0.0165 (6) | |
B11 | 0.4415 (3) | 0.16950 (14) | 0.81762 (9) | 0.0171 (9) | |
B12 | 0.5250 (4) | 0.13282 (13) | 0.86569 (9) | 0.0180 (9) | |
B13 | 0.5290 (4) | 0.21841 (13) | 0.86011 (9) | 0.0173 (9) | |
C16 | 0.3934 (3) | 0.12593 (11) | 0.76926 (8) | 0.0247 (8) | |
H16A | 0.3459 | 0.1017 | 0.7812 | 0.030* | |
H16B | 0.4837 | 0.1153 | 0.7661 | 0.030* | |
C17 | 0.3296 (3) | 0.13431 (12) | 0.73696 (8) | 0.0302 (9) | |
H17A | 0.2371 | 0.1417 | 0.7405 | 0.036* | |
H17B | 0.3703 | 0.1616 | 0.7268 | 0.036* | |
C18 | 0.3388 (3) | 0.09373 (12) | 0.71400 (8) | 0.0303 (9) | |
H18A | 0.2901 | 0.0673 | 0.7231 | 0.036* | |
H18B | 0.2972 | 0.1023 | 0.6934 | 0.036* | |
C19 | 0.5482 (4) | 0.11612 (14) | 0.69311 (9) | 0.0459 (11) | |
H19A | 0.6339 | 0.1043 | 0.6873 | 0.069* | |
H19B | 0.5577 | 0.1415 | 0.7086 | 0.069* | |
H19C | 0.5043 | 0.1275 | 0.6738 | 0.069* | |
C20 | 0.4704 (4) | 0.03893 (13) | 0.68640 (9) | 0.0490 (12) | |
H20A | 0.4173 | 0.0145 | 0.6960 | 0.074* | |
H20B | 0.5590 | 0.0276 | 0.6835 | 0.074* | |
H20C | 0.4341 | 0.0477 | 0.6655 | 0.074* | |
C21 | 0.5847 (3) | 0.05229 (11) | 0.86386 (8) | 0.0254 (9) | |
H21A | 0.6597 | 0.0314 | 0.8667 | 0.030* | |
H21B | 0.5585 | 0.0512 | 0.8410 | 0.030* | |
C22 | 0.4729 (3) | 0.03554 (12) | 0.88477 (8) | 0.0282 (9) | |
H22A | 0.4462 | 0.0043 | 0.8777 | 0.034* | |
H22B | 0.5021 | 0.0334 | 0.9074 | 0.034* | |
C23 | 0.3584 (3) | 0.06801 (11) | 0.88268 (8) | 0.0244 (9) | |
H23A | 0.3211 | 0.0665 | 0.8608 | 0.029* | |
H23B | 0.2910 | 0.0579 | 0.8981 | 0.029* | |
C24 | 0.4330 (3) | 0.12126 (12) | 0.92439 (7) | 0.0232 (8) | |
H24A | 0.4493 | 0.1538 | 0.9294 | 0.035* | |
H24B | 0.5114 | 0.1032 | 0.9285 | 0.035* | |
H24C | 0.3623 | 0.1097 | 0.9379 | 0.035* | |
C25 | 0.2828 (3) | 0.14792 (12) | 0.88459 (8) | 0.0250 (9) | |
H25A | 0.2166 | 0.1417 | 0.9009 | 0.038* | |
H25B | 0.2468 | 0.1422 | 0.8632 | 0.038* | |
H25C | 0.3106 | 0.1802 | 0.8862 | 0.038* | |
C26 | 0.5323 (3) | 0.26389 (12) | 0.90858 (8) | 0.0235 (8) | |
H26A | 0.5477 | 0.2356 | 0.9214 | 0.028* | |
H26B | 0.4793 | 0.2853 | 0.9217 | 0.028* | |
C27 | 0.6606 (3) | 0.28657 (12) | 0.90091 (8) | 0.0226 (8) | |
H27A | 0.7095 | 0.2914 | 0.9211 | 0.027* | |
H27B | 0.6447 | 0.3172 | 0.8911 | 0.027* | |
C28 | 0.7416 (3) | 0.25740 (11) | 0.87802 (7) | 0.0197 (8) | |
H28A | 0.8197 | 0.2750 | 0.8716 | 0.024* | |
H28B | 0.7704 | 0.2290 | 0.8892 | 0.024* | |
C29 | 0.6381 (3) | 0.28626 (11) | 0.82886 (8) | 0.0231 (8) | |
H29A | 0.7191 | 0.3025 | 0.8242 | 0.035* | |
H29B | 0.5801 | 0.3068 | 0.8409 | 0.035* | |
H29C | 0.5966 | 0.2771 | 0.8087 | 0.035* | |
C30 | 0.7468 (3) | 0.21278 (11) | 0.82889 (8) | 0.0251 (8) | |
H30A | 0.6970 | 0.2021 | 0.8103 | 0.038* | |
H30B | 0.7726 | 0.1861 | 0.8419 | 0.038* | |
H30C | 0.8243 | 0.2292 | 0.8215 | 0.038* | |
O21 | 0.52542 (19) | 0.69331 (7) | 1.00038 (5) | 0.0170 (5) | |
O22 | 0.54608 (19) | 0.61358 (7) | 0.98539 (5) | 0.0160 (5) | |
O23 | 0.42813 (19) | 0.66632 (7) | 0.95068 (5) | 0.0159 (5) | |
O24 | 0.62368 (19) | 0.64172 (7) | 1.03554 (5) | 0.0202 (5) | |
O25 | 0.39802 (19) | 0.58601 (7) | 0.94455 (5) | 0.0194 (5) | |
O26 | 0.52482 (19) | 0.74252 (7) | 0.95511 (5) | 0.0183 (5) | |
N21 | 0.5962 (3) | 0.58871 (9) | 1.13078 (6) | 0.0235 (7) | |
N22 | 0.6124 (2) | 0.61857 (8) | 0.92794 (6) | 0.0148 (6) | |
N23 | 0.3166 (2) | 0.72696 (9) | 0.98260 (6) | 0.0161 (6) | |
B21 | 0.5632 (3) | 0.64902 (14) | 1.00627 (9) | 0.0178 (9) | |
B22 | 0.4851 (3) | 0.62246 (13) | 0.95425 (9) | 0.0167 (9) | |
B23 | 0.4582 (3) | 0.70478 (13) | 0.97070 (9) | 0.0188 (9) | |
C31 | 0.6840 (3) | 0.59801 (11) | 1.04172 (8) | 0.0251 (9) | |
H31A | 0.7678 | 0.5962 | 1.0303 | 0.030* | |
H31B | 0.6280 | 0.5726 | 1.0339 | 0.030* | |
C32 | 0.7059 (3) | 0.59288 (12) | 1.07756 (8) | 0.0240 (8) | |
H32A | 0.7609 | 0.5654 | 1.0815 | 0.029* | |
H32B | 0.7527 | 0.6204 | 1.0856 | 0.029* | |
C33 | 0.5801 (3) | 0.58765 (11) | 1.09589 (8) | 0.0234 (8) | |
H33A | 0.5206 | 0.6129 | 1.0895 | 0.028* | |
H33B | 0.5392 | 0.5580 | 1.0898 | 0.028* | |
C34 | 0.6825 (3) | 0.55266 (12) | 1.14245 (8) | 0.0319 (9) | |
H34A | 0.6536 | 0.5226 | 1.1343 | 0.048* | |
H34B | 0.6814 | 0.5523 | 1.1660 | 0.048* | |
H34C | 0.7708 | 0.5588 | 1.1349 | 0.048* | |
C35 | 0.4699 (3) | 0.58430 (12) | 1.14642 (8) | 0.0342 (10) | |
H35A | 0.4318 | 0.5543 | 1.1410 | 0.051* | |
H35B | 0.4127 | 0.6091 | 1.1390 | 0.051* | |
H35C | 0.4808 | 0.5866 | 1.1697 | 0.051* | |
C36 | 0.4485 (3) | 0.54056 (11) | 0.94657 (8) | 0.0225 (8) | |
H36A | 0.3797 | 0.5180 | 0.9412 | 0.027* | |
H36B | 0.4771 | 0.5344 | 0.9688 | 0.027* | |
C37 | 0.5625 (3) | 0.53418 (11) | 0.92370 (8) | 0.0233 (8) | |
H37A | 0.6004 | 0.5031 | 0.9269 | 0.028* | |
H37B | 0.5314 | 0.5362 | 0.9013 | 0.028* | |
C38 | 0.6655 (3) | 0.57060 (10) | 0.92935 (8) | 0.0203 (8) | |
H38A | 0.7054 | 0.5655 | 0.9507 | 0.024* | |
H38B | 0.7341 | 0.5672 | 0.9129 | 0.024* | |
C39 | 0.5701 (3) | 0.62964 (11) | 0.89477 (7) | 0.0220 (8) | |
H39A | 0.5430 | 0.6621 | 0.8937 | 0.033* | |
H39B | 0.4973 | 0.6097 | 0.8889 | 0.033* | |
H39C | 0.6420 | 0.6245 | 0.8799 | 0.033* | |
C40 | 0.7173 (3) | 0.65145 (11) | 0.93662 (8) | 0.0184 (8) | |
H40A | 0.7844 | 0.6509 | 0.9200 | 0.028* | |
H40B | 0.7551 | 0.6424 | 0.9573 | 0.028* | |
H40C | 0.6815 | 0.6827 | 0.9383 | 0.028* | |
C41 | 0.4624 (3) | 0.75876 (11) | 0.92683 (8) | 0.0224 (8) | |
H41A | 0.4518 | 0.7328 | 0.9115 | 0.027* | |
H41B | 0.5170 | 0.7826 | 0.9164 | 0.027* | |
C42 | 0.3301 (3) | 0.77927 (11) | 0.93470 (8) | 0.0219 (8) | |
H42A | 0.3418 | 0.8079 | 0.9474 | 0.026* | |
H42B | 0.2853 | 0.7876 | 0.9145 | 0.026* | |
C43 | 0.2472 (3) | 0.74550 (11) | 0.95354 (7) | 0.0218 (8) | |
H43A | 0.1668 | 0.7612 | 0.9605 | 0.026* | |
H43B | 0.2225 | 0.7194 | 0.9394 | 0.026* | |
C44 | 0.3376 (3) | 0.76490 (11) | 1.00641 (8) | 0.0220 (8) | |
H44A | 0.2543 | 0.7792 | 1.0118 | 0.033* | |
H44B | 0.3953 | 0.7883 | 0.9972 | 0.033* | |
H44C | 0.3768 | 0.7521 | 1.0259 | 0.033* | |
C45 | 0.2347 (3) | 0.69146 (11) | 0.99790 (8) | 0.0230 (8) | |
H45A | 0.2786 | 0.6794 | 1.0170 | 0.035* | |
H45B | 0.2192 | 0.6662 | 0.9827 | 0.035* | |
H45C | 0.1518 | 0.7052 | 1.0042 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0196 (13) | 0.0197 (13) | 0.0162 (13) | 0.0001 (10) | −0.0052 (10) | 0.0007 (10) |
O2 | 0.0205 (12) | 0.0209 (13) | 0.0127 (13) | −0.0031 (11) | −0.0032 (10) | 0.0021 (10) |
O3 | 0.0163 (12) | 0.0189 (13) | 0.0155 (13) | −0.0035 (10) | −0.0006 (9) | 0.0022 (10) |
O4 | 0.0409 (15) | 0.0265 (14) | 0.0163 (14) | 0.0048 (12) | −0.0106 (11) | −0.0043 (11) |
O5 | 0.0210 (12) | 0.0177 (13) | 0.0212 (14) | −0.0013 (11) | 0.0001 (10) | 0.0005 (10) |
O6 | 0.0145 (12) | 0.0254 (13) | 0.0173 (14) | −0.0006 (11) | −0.0004 (10) | −0.0050 (10) |
N1 | 0.0257 (17) | 0.0262 (17) | 0.0229 (18) | −0.0020 (14) | −0.0017 (13) | −0.0010 (14) |
N2 | 0.0149 (15) | 0.0271 (17) | 0.0150 (16) | −0.0011 (13) | −0.0007 (12) | −0.0002 (13) |
N3 | 0.0171 (15) | 0.0196 (16) | 0.0124 (16) | 0.0018 (13) | −0.0010 (12) | 0.0001 (12) |
B1 | 0.011 (2) | 0.024 (2) | 0.025 (3) | −0.0004 (18) | 0.0040 (17) | 0.0008 (19) |
B2 | 0.015 (2) | 0.023 (2) | 0.015 (2) | −0.0040 (18) | −0.0012 (17) | 0.0002 (17) |
B3 | 0.0115 (19) | 0.025 (2) | 0.018 (2) | −0.0027 (18) | −0.0014 (17) | −0.0040 (18) |
C1 | 0.040 (2) | 0.025 (2) | 0.019 (2) | 0.0025 (18) | −0.0102 (17) | −0.0052 (17) |
C2 | 0.028 (2) | 0.030 (2) | 0.024 (2) | −0.0027 (17) | −0.0025 (16) | −0.0060 (17) |
C3 | 0.027 (2) | 0.032 (2) | 0.032 (2) | −0.0019 (18) | −0.0006 (17) | −0.0017 (18) |
C4 | 0.037 (2) | 0.040 (2) | 0.028 (2) | −0.002 (2) | −0.0052 (18) | 0.0024 (19) |
C5 | 0.052 (3) | 0.033 (2) | 0.032 (2) | −0.006 (2) | 0.003 (2) | −0.0049 (19) |
C6 | 0.030 (2) | 0.019 (2) | 0.026 (2) | −0.0019 (16) | −0.0015 (16) | −0.0020 (16) |
C7 | 0.035 (2) | 0.022 (2) | 0.025 (2) | −0.0065 (18) | −0.0029 (17) | 0.0022 (16) |
C8 | 0.029 (2) | 0.028 (2) | 0.025 (2) | −0.0130 (18) | 0.0001 (16) | 0.0040 (17) |
C9 | 0.0184 (19) | 0.034 (2) | 0.016 (2) | −0.0045 (16) | 0.0019 (15) | 0.0008 (16) |
C10 | 0.0139 (18) | 0.035 (2) | 0.026 (2) | −0.0033 (17) | 0.0016 (15) | −0.0010 (17) |
C11 | 0.024 (2) | 0.024 (2) | 0.016 (2) | −0.0028 (17) | 0.0015 (15) | −0.0046 (15) |
C12 | 0.0238 (19) | 0.028 (2) | 0.017 (2) | −0.0044 (17) | −0.0015 (15) | −0.0030 (16) |
C13 | 0.0133 (17) | 0.027 (2) | 0.023 (2) | −0.0063 (15) | −0.0060 (15) | 0.0023 (16) |
C14 | 0.023 (2) | 0.025 (2) | 0.021 (2) | −0.0023 (16) | 0.0024 (15) | 0.0051 (16) |
C15 | 0.0210 (19) | 0.031 (2) | 0.021 (2) | 0.0036 (17) | 0.0063 (16) | −0.0051 (17) |
O11 | 0.0172 (12) | 0.0199 (13) | 0.0162 (13) | −0.0008 (10) | −0.0050 (10) | −0.0021 (10) |
O12 | 0.0224 (13) | 0.0218 (13) | 0.0129 (13) | 0.0005 (11) | −0.0027 (10) | −0.0011 (10) |
O13 | 0.0177 (12) | 0.0188 (13) | 0.0148 (13) | −0.0029 (10) | −0.0040 (10) | −0.0004 (10) |
O14 | 0.0316 (14) | 0.0229 (14) | 0.0169 (14) | 0.0023 (11) | −0.0081 (11) | −0.0035 (10) |
O15 | 0.0180 (12) | 0.0182 (13) | 0.0205 (13) | 0.0003 (10) | −0.0038 (10) | −0.0041 (10) |
O16 | 0.0154 (12) | 0.0254 (14) | 0.0180 (14) | −0.0001 (11) | −0.0017 (10) | −0.0034 (10) |
N11 | 0.0388 (19) | 0.0314 (19) | 0.0199 (18) | 0.0020 (16) | 0.0023 (15) | −0.0027 (14) |
N12 | 0.0177 (15) | 0.0243 (17) | 0.0132 (16) | −0.0042 (13) | −0.0005 (12) | −0.0012 (12) |
N13 | 0.0167 (15) | 0.0180 (16) | 0.0149 (16) | −0.0013 (13) | −0.0037 (12) | 0.0021 (12) |
B11 | 0.012 (2) | 0.022 (2) | 0.017 (2) | 0.0016 (18) | 0.0043 (17) | −0.0032 (18) |
B12 | 0.016 (2) | 0.026 (2) | 0.012 (2) | −0.0002 (19) | −0.0030 (17) | 0.0050 (17) |
B13 | 0.014 (2) | 0.023 (2) | 0.015 (2) | −0.0030 (18) | −0.0003 (17) | 0.0008 (17) |
C16 | 0.035 (2) | 0.024 (2) | 0.016 (2) | 0.0039 (17) | −0.0014 (16) | −0.0037 (16) |
C17 | 0.035 (2) | 0.034 (2) | 0.021 (2) | 0.0076 (19) | −0.0089 (17) | −0.0076 (17) |
C18 | 0.033 (2) | 0.036 (2) | 0.022 (2) | −0.0034 (19) | −0.0038 (17) | −0.0042 (17) |
C19 | 0.046 (3) | 0.066 (3) | 0.026 (3) | −0.009 (2) | 0.0018 (19) | −0.005 (2) |
C20 | 0.081 (3) | 0.043 (3) | 0.023 (2) | 0.011 (2) | 0.000 (2) | −0.007 (2) |
C21 | 0.029 (2) | 0.023 (2) | 0.024 (2) | 0.0015 (17) | −0.0071 (17) | −0.0036 (16) |
C22 | 0.038 (2) | 0.020 (2) | 0.027 (2) | −0.0070 (18) | −0.0073 (18) | 0.0005 (16) |
C23 | 0.028 (2) | 0.023 (2) | 0.022 (2) | −0.0077 (17) | 0.0006 (16) | 0.0033 (16) |
C24 | 0.022 (2) | 0.033 (2) | 0.015 (2) | −0.0062 (16) | −0.0029 (15) | 0.0026 (16) |
C25 | 0.0117 (18) | 0.035 (2) | 0.029 (2) | −0.0008 (16) | 0.0028 (15) | −0.0017 (17) |
C26 | 0.029 (2) | 0.028 (2) | 0.014 (2) | −0.0046 (17) | 0.0023 (16) | −0.0057 (15) |
C27 | 0.027 (2) | 0.027 (2) | 0.013 (2) | −0.0061 (17) | −0.0013 (15) | −0.0035 (16) |
C28 | 0.0155 (18) | 0.025 (2) | 0.019 (2) | −0.0049 (16) | −0.0037 (15) | 0.0020 (15) |
C29 | 0.0194 (19) | 0.024 (2) | 0.026 (2) | −0.0015 (16) | −0.0014 (15) | 0.0063 (16) |
C30 | 0.023 (2) | 0.028 (2) | 0.024 (2) | 0.0045 (17) | 0.0074 (17) | 0.0007 (17) |
O21 | 0.0178 (12) | 0.0183 (13) | 0.0148 (13) | 0.0023 (10) | −0.0062 (10) | 0.0002 (10) |
O22 | 0.0180 (12) | 0.0180 (12) | 0.0119 (13) | 0.0015 (10) | −0.0005 (9) | 0.0018 (10) |
O23 | 0.0153 (12) | 0.0185 (12) | 0.0141 (13) | 0.0033 (10) | −0.0021 (9) | −0.0012 (10) |
O24 | 0.0253 (13) | 0.0210 (13) | 0.0141 (13) | 0.0060 (11) | −0.0056 (10) | −0.0010 (10) |
O25 | 0.0180 (12) | 0.0179 (13) | 0.0224 (14) | −0.0020 (11) | 0.0012 (10) | −0.0007 (10) |
O26 | 0.0140 (12) | 0.0201 (13) | 0.0206 (14) | 0.0017 (10) | −0.0007 (10) | 0.0031 (10) |
N21 | 0.0273 (17) | 0.0270 (18) | 0.0162 (17) | 0.0010 (14) | −0.0018 (13) | 0.0009 (13) |
N22 | 0.0154 (14) | 0.0163 (15) | 0.0126 (16) | −0.0004 (12) | 0.0005 (12) | −0.0012 (12) |
N23 | 0.0162 (15) | 0.0189 (16) | 0.0132 (16) | −0.0013 (12) | −0.0019 (12) | 0.0015 (12) |
B21 | 0.0089 (19) | 0.031 (3) | 0.013 (2) | −0.0037 (18) | 0.0046 (16) | 0.0014 (18) |
B22 | 0.015 (2) | 0.025 (2) | 0.011 (2) | −0.0020 (18) | 0.0028 (16) | −0.0007 (17) |
B23 | 0.013 (2) | 0.025 (2) | 0.019 (2) | −0.0009 (18) | −0.0001 (17) | −0.0029 (18) |
C31 | 0.027 (2) | 0.026 (2) | 0.023 (2) | 0.0060 (17) | −0.0001 (16) | 0.0042 (16) |
C32 | 0.024 (2) | 0.029 (2) | 0.019 (2) | −0.0001 (17) | −0.0064 (15) | 0.0064 (16) |
C33 | 0.025 (2) | 0.021 (2) | 0.025 (2) | 0.0020 (16) | −0.0043 (16) | −0.0020 (16) |
C34 | 0.036 (2) | 0.039 (2) | 0.020 (2) | 0.0071 (19) | −0.0032 (17) | 0.0073 (18) |
C35 | 0.038 (2) | 0.038 (2) | 0.027 (2) | 0.006 (2) | 0.0059 (19) | 0.0026 (18) |
C36 | 0.026 (2) | 0.0171 (19) | 0.025 (2) | −0.0015 (16) | 0.0023 (16) | −0.0014 (15) |
C37 | 0.028 (2) | 0.021 (2) | 0.021 (2) | 0.0043 (17) | 0.0026 (16) | −0.0030 (16) |
C38 | 0.0195 (19) | 0.0176 (19) | 0.024 (2) | 0.0045 (16) | 0.0039 (15) | 0.0025 (16) |
C39 | 0.027 (2) | 0.028 (2) | 0.011 (2) | −0.0006 (17) | −0.0008 (14) | 0.0023 (15) |
C40 | 0.0142 (17) | 0.023 (2) | 0.018 (2) | −0.0014 (15) | −0.0012 (14) | −0.0020 (15) |
C41 | 0.0234 (19) | 0.0215 (19) | 0.022 (2) | 0.0035 (17) | 0.0042 (16) | 0.0085 (16) |
C42 | 0.025 (2) | 0.027 (2) | 0.013 (2) | 0.0063 (17) | −0.0015 (16) | 0.0043 (16) |
C43 | 0.0207 (19) | 0.027 (2) | 0.017 (2) | 0.0085 (16) | −0.0053 (15) | −0.0021 (16) |
C44 | 0.0231 (19) | 0.026 (2) | 0.017 (2) | 0.0032 (16) | −0.0032 (15) | −0.0071 (16) |
C45 | 0.0173 (18) | 0.027 (2) | 0.025 (2) | −0.0010 (16) | 0.0061 (16) | 0.0003 (16) |
O1—B1 | 1.359 (4) | C19—H19C | 0.9800 |
O1—B3 | 1.442 (4) | C20—H20A | 0.9800 |
O2—B1 | 1.358 (4) | C20—H20B | 0.9800 |
O2—B2 | 1.467 (4) | C20—H20C | 0.9800 |
O3—B2 | 1.394 (4) | C21—C22 | 1.525 (4) |
O3—B3 | 1.430 (4) | C21—H21A | 0.9900 |
O4—B1 | 1.383 (4) | C21—H21B | 0.9900 |
O4—C1 | 1.435 (4) | C22—C23 | 1.513 (4) |
O5—C6 | 1.421 (4) | C22—H22A | 0.9900 |
O5—B2 | 1.446 (4) | C22—H22B | 0.9900 |
O6—C11 | 1.426 (3) | C23—H23A | 0.9900 |
O6—B3 | 1.445 (4) | C23—H23B | 0.9900 |
N1—C4 | 1.457 (4) | C24—H24A | 0.9800 |
N1—C3 | 1.460 (4) | C24—H24B | 0.9800 |
N1—C5 | 1.466 (4) | C24—H24C | 0.9800 |
N2—C10 | 1.485 (4) | C25—H25A | 0.9800 |
N2—C9 | 1.489 (4) | C25—H25B | 0.9800 |
N2—C8 | 1.505 (4) | C25—H25C | 0.9800 |
N2—B2 | 1.721 (4) | C26—C27 | 1.514 (4) |
N3—C15 | 1.483 (4) | C26—H26A | 0.9900 |
N3—C14 | 1.491 (4) | C26—H26B | 0.9900 |
N3—C13 | 1.505 (4) | C27—C28 | 1.523 (4) |
N3—B3 | 1.685 (4) | C27—H27A | 0.9900 |
C1—C2 | 1.517 (5) | C27—H27B | 0.9900 |
C1—H1A | 0.9900 | C28—H28A | 0.9900 |
C1—H1B | 0.9900 | C28—H28B | 0.9900 |
C2—C3 | 1.516 (4) | C29—H29A | 0.9800 |
C2—H2A | 0.9900 | C29—H29B | 0.9800 |
C2—H2B | 0.9900 | C29—H29C | 0.9800 |
C3—H3A | 0.9900 | C30—H30A | 0.9800 |
C3—H3B | 0.9900 | C30—H30B | 0.9800 |
C4—H4A | 0.9800 | C30—H30C | 0.9800 |
C4—H4B | 0.9800 | O21—B21 | 1.361 (4) |
C4—H4C | 0.9800 | O21—B23 | 1.456 (4) |
C5—H5A | 0.9800 | O22—B21 | 1.356 (4) |
C5—H5B | 0.9800 | O22—B22 | 1.464 (4) |
C5—H5C | 0.9800 | O23—B22 | 1.406 (4) |
C6—C7 | 1.520 (4) | O23—B23 | 1.424 (4) |
C6—H6A | 0.9900 | O24—B21 | 1.386 (4) |
C6—H6B | 0.9900 | O24—C31 | 1.432 (4) |
C7—C8 | 1.514 (4) | O25—C36 | 1.416 (3) |
C7—H7A | 0.9900 | O25—B22 | 1.444 (4) |
C7—H7B | 0.9900 | O26—C41 | 1.423 (4) |
C8—H8A | 0.9900 | O26—B23 | 1.444 (4) |
C8—H8B | 0.9900 | N21—C34 | 1.455 (4) |
C9—H9A | 0.9800 | N21—C33 | 1.463 (4) |
C9—H9B | 0.9800 | N21—C35 | 1.464 (4) |
C9—H9C | 0.9800 | N22—C39 | 1.484 (4) |
C10—H10A | 0.9800 | N22—C40 | 1.486 (4) |
C10—H10B | 0.9800 | N22—C38 | 1.493 (4) |
C10—H10C | 0.9800 | N22—B22 | 1.715 (4) |
C11—C12 | 1.522 (4) | N23—C45 | 1.475 (4) |
C11—H11A | 0.9900 | N23—C44 | 1.495 (4) |
C11—H11B | 0.9900 | N23—C43 | 1.505 (4) |
C12—C13 | 1.517 (4) | N23—B23 | 1.672 (4) |
C12—H12A | 0.9900 | C31—C32 | 1.516 (4) |
C12—H12B | 0.9900 | C31—H31A | 0.9900 |
C13—H13A | 0.9900 | C31—H31B | 0.9900 |
C13—H13B | 0.9900 | C32—C33 | 1.515 (4) |
C14—H14A | 0.9800 | C32—H32A | 0.9900 |
C14—H14B | 0.9800 | C32—H32B | 0.9900 |
C14—H14C | 0.9800 | C33—H33A | 0.9900 |
C15—H15A | 0.9800 | C33—H33B | 0.9900 |
C15—H15B | 0.9800 | C34—H34A | 0.9800 |
C15—H15C | 0.9800 | C34—H34B | 0.9800 |
O11—B11 | 1.355 (4) | C34—H34C | 0.9800 |
O11—B13 | 1.458 (4) | C35—H35A | 0.9800 |
O12—B11 | 1.360 (4) | C35—H35B | 0.9800 |
O12—B12 | 1.459 (4) | C35—H35C | 0.9800 |
O13—B12 | 1.399 (4) | C36—C37 | 1.525 (4) |
O13—B13 | 1.423 (4) | C36—H36A | 0.9900 |
O14—B11 | 1.381 (4) | C36—H36B | 0.9900 |
O14—C16 | 1.419 (4) | C37—C38 | 1.516 (4) |
O15—C21 | 1.413 (4) | C37—H37A | 0.9900 |
O15—B12 | 1.441 (4) | C37—H37B | 0.9900 |
O16—C26 | 1.423 (4) | C38—H38A | 0.9900 |
O16—B13 | 1.451 (4) | C38—H38B | 0.9900 |
N11—C20 | 1.454 (4) | C39—H39A | 0.9800 |
N11—C18 | 1.462 (4) | C39—H39B | 0.9800 |
N11—C19 | 1.464 (4) | C39—H39C | 0.9800 |
N12—C24 | 1.488 (4) | C40—H40A | 0.9800 |
N12—C25 | 1.495 (4) | C40—H40B | 0.9800 |
N12—C23 | 1.496 (4) | C40—H40C | 0.9800 |
N12—B12 | 1.733 (4) | C41—C42 | 1.525 (4) |
N13—C30 | 1.478 (4) | C41—H41A | 0.9900 |
N13—C29 | 1.490 (4) | C41—H41B | 0.9900 |
N13—C28 | 1.506 (4) | C42—C43 | 1.518 (4) |
N13—B13 | 1.676 (4) | C42—H42A | 0.9900 |
C16—C17 | 1.518 (4) | C42—H42B | 0.9900 |
C16—H16A | 0.9900 | C43—H43A | 0.9900 |
C16—H16B | 0.9900 | C43—H43B | 0.9900 |
C17—C18 | 1.517 (4) | C44—H44A | 0.9800 |
C17—H17A | 0.9900 | C44—H44B | 0.9800 |
C17—H17B | 0.9900 | C44—H44C | 0.9800 |
C18—H18A | 0.9900 | C45—H45A | 0.9800 |
C18—H18B | 0.9900 | C45—H45B | 0.9800 |
C19—H19A | 0.9800 | C45—H45C | 0.9800 |
C19—H19B | 0.9800 | ||
B1—O1—B3 | 120.2 (3) | N11—C20—H20C | 109.5 |
B1—O2—B2 | 118.4 (3) | H20A—C20—H20C | 109.5 |
B2—O3—B3 | 122.9 (3) | H20B—C20—H20C | 109.5 |
B1—O4—C1 | 123.8 (3) | O15—C21—C22 | 111.3 (3) |
C6—O5—B2 | 116.1 (2) | O15—C21—H21A | 109.4 |
C11—O6—B3 | 114.6 (2) | C22—C21—H21A | 109.4 |
C4—N1—C3 | 112.1 (3) | O15—C21—H21B | 109.4 |
C4—N1—C5 | 108.2 (3) | C22—C21—H21B | 109.4 |
C3—N1—C5 | 109.0 (3) | H21A—C21—H21B | 108.0 |
C10—N2—C9 | 106.8 (2) | C23—C22—C21 | 111.2 (3) |
C10—N2—C8 | 109.3 (2) | C23—C22—H22A | 109.4 |
C9—N2—C8 | 110.4 (2) | C21—C22—H22A | 109.4 |
C10—N2—B2 | 111.5 (2) | C23—C22—H22B | 109.4 |
C9—N2—B2 | 109.8 (2) | C21—C22—H22B | 109.4 |
C8—N2—B2 | 109.0 (2) | H22A—C22—H22B | 108.0 |
C15—N3—C14 | 107.5 (2) | N12—C23—C22 | 111.6 (3) |
C15—N3—C13 | 108.1 (2) | N12—C23—H23A | 109.3 |
C14—N3—C13 | 110.7 (2) | C22—C23—H23A | 109.3 |
C15—N3—B3 | 111.1 (2) | N12—C23—H23B | 109.3 |
C14—N3—B3 | 110.7 (2) | C22—C23—H23B | 109.3 |
C13—N3—B3 | 108.6 (2) | H23A—C23—H23B | 108.0 |
O2—B1—O1 | 123.4 (3) | N12—C24—H24A | 109.5 |
O2—B1—O4 | 122.4 (3) | N12—C24—H24B | 109.5 |
O1—B1—O4 | 114.2 (3) | H24A—C24—H24B | 109.5 |
O3—B2—O5 | 111.4 (3) | N12—C24—H24C | 109.5 |
O3—B2—O2 | 116.2 (3) | H24A—C24—H24C | 109.5 |
O5—B2—O2 | 112.7 (3) | H24B—C24—H24C | 109.5 |
O3—B2—N2 | 107.6 (3) | N12—C25—H25A | 109.5 |
O5—B2—N2 | 103.7 (2) | N12—C25—H25B | 109.5 |
O2—B2—N2 | 104.0 (2) | H25A—C25—H25B | 109.5 |
O3—B3—O1 | 115.4 (3) | N12—C25—H25C | 109.5 |
O3—B3—O6 | 114.9 (3) | H25A—C25—H25C | 109.5 |
O1—B3—O6 | 109.7 (3) | H25B—C25—H25C | 109.5 |
O3—B3—N3 | 105.6 (2) | O16—C26—C27 | 111.5 (3) |
O1—B3—N3 | 105.6 (3) | O16—C26—H26A | 109.3 |
O6—B3—N3 | 104.6 (2) | C27—C26—H26A | 109.3 |
O4—C1—C2 | 107.2 (3) | O16—C26—H26B | 109.3 |
O4—C1—H1A | 110.3 | C27—C26—H26B | 109.3 |
C2—C1—H1A | 110.3 | H26A—C26—H26B | 108.0 |
O4—C1—H1B | 110.3 | C26—C27—C28 | 111.9 (3) |
C2—C1—H1B | 110.3 | C26—C27—H27A | 109.2 |
H1A—C1—H1B | 108.5 | C28—C27—H27A | 109.2 |
C3—C2—C1 | 115.4 (3) | C26—C27—H27B | 109.2 |
C3—C2—H2A | 108.4 | C28—C27—H27B | 109.2 |
C1—C2—H2A | 108.4 | H27A—C27—H27B | 107.9 |
C3—C2—H2B | 108.4 | N13—C28—C27 | 111.6 (3) |
C1—C2—H2B | 108.4 | N13—C28—H28A | 109.3 |
H2A—C2—H2B | 107.5 | C27—C28—H28A | 109.3 |
N1—C3—C2 | 114.9 (3) | N13—C28—H28B | 109.3 |
N1—C3—H3A | 108.5 | C27—C28—H28B | 109.3 |
C2—C3—H3A | 108.5 | H28A—C28—H28B | 108.0 |
N1—C3—H3B | 108.5 | N13—C29—H29A | 109.5 |
C2—C3—H3B | 108.5 | N13—C29—H29B | 109.5 |
H3A—C3—H3B | 107.5 | H29A—C29—H29B | 109.5 |
N1—C4—H4A | 109.5 | N13—C29—H29C | 109.5 |
N1—C4—H4B | 109.5 | H29A—C29—H29C | 109.5 |
H4A—C4—H4B | 109.5 | H29B—C29—H29C | 109.5 |
N1—C4—H4C | 109.5 | N13—C30—H30A | 109.5 |
H4A—C4—H4C | 109.5 | N13—C30—H30B | 109.5 |
H4B—C4—H4C | 109.5 | H30A—C30—H30B | 109.5 |
N1—C5—H5A | 109.5 | N13—C30—H30C | 109.5 |
N1—C5—H5B | 109.5 | H30A—C30—H30C | 109.5 |
H5A—C5—H5B | 109.5 | H30B—C30—H30C | 109.5 |
N1—C5—H5C | 109.5 | B21—O21—B23 | 120.3 (3) |
H5A—C5—H5C | 109.5 | B21—O22—B22 | 119.5 (3) |
H5B—C5—H5C | 109.5 | B22—O23—B23 | 123.4 (3) |
O5—C6—C7 | 111.5 (3) | B21—O24—C31 | 119.3 (3) |
O5—C6—H6A | 109.3 | C36—O25—B22 | 115.5 (2) |
C7—C6—H6A | 109.3 | C41—O26—B23 | 113.9 (2) |
O5—C6—H6B | 109.3 | C34—N21—C33 | 112.7 (3) |
C7—C6—H6B | 109.3 | C34—N21—C35 | 109.6 (3) |
H6A—C6—H6B | 108.0 | C33—N21—C35 | 109.8 (3) |
C8—C7—C6 | 111.0 (3) | C39—N22—C40 | 107.7 (2) |
C8—C7—H7A | 109.4 | C39—N22—C38 | 110.2 (2) |
C6—C7—H7A | 109.4 | C40—N22—C38 | 108.5 (2) |
C8—C7—H7B | 109.4 | C39—N22—B22 | 110.7 (2) |
C6—C7—H7B | 109.4 | C40—N22—B22 | 111.2 (2) |
H7A—C7—H7B | 108.0 | C38—N22—B22 | 108.5 (2) |
N2—C8—C7 | 112.5 (3) | C45—N23—C44 | 107.9 (2) |
N2—C8—H8A | 109.1 | C45—N23—C43 | 108.8 (2) |
C7—C8—H8A | 109.1 | C44—N23—C43 | 109.9 (2) |
N2—C8—H8B | 109.1 | C45—N23—B23 | 111.3 (2) |
C7—C8—H8B | 109.1 | C44—N23—B23 | 110.5 (2) |
H8A—C8—H8B | 107.8 | C43—N23—B23 | 108.4 (2) |
N2—C9—H9A | 109.5 | O22—B21—O21 | 123.9 (3) |
N2—C9—H9B | 109.5 | O22—B21—O24 | 120.5 (3) |
H9A—C9—H9B | 109.5 | O21—B21—O24 | 115.6 (3) |
N2—C9—H9C | 109.5 | O23—B22—O25 | 111.6 (3) |
H9A—C9—H9C | 109.5 | O23—B22—O22 | 115.6 (3) |
H9B—C9—H9C | 109.5 | O25—B22—O22 | 112.8 (3) |
N2—C10—H10A | 109.5 | O23—B22—N22 | 108.2 (3) |
N2—C10—H10B | 109.5 | O25—B22—N22 | 104.6 (2) |
H10A—C10—H10B | 109.5 | O22—B22—N22 | 103.0 (2) |
N2—C10—H10C | 109.5 | O23—B23—O26 | 115.5 (3) |
H10A—C10—H10C | 109.5 | O23—B23—O21 | 115.0 (3) |
H10B—C10—H10C | 109.5 | O26—B23—O21 | 109.0 (3) |
O6—C11—C12 | 111.3 (2) | O23—B23—N23 | 106.4 (2) |
O6—C11—H11A | 109.4 | O26—B23—N23 | 105.1 (3) |
C12—C11—H11A | 109.4 | O21—B23—N23 | 104.7 (3) |
O6—C11—H11B | 109.4 | O24—C31—C32 | 109.2 (3) |
C12—C11—H11B | 109.4 | O24—C31—H31A | 109.8 |
H11A—C11—H11B | 108.0 | C32—C31—H31A | 109.9 |
C13—C12—C11 | 112.1 (3) | O24—C31—H31B | 109.8 |
C13—C12—H12A | 109.2 | C32—C31—H31B | 109.9 |
C11—C12—H12A | 109.2 | H31A—C31—H31B | 108.3 |
C13—C12—H12B | 109.2 | C33—C32—C31 | 112.2 (3) |
C11—C12—H12B | 109.2 | C33—C32—H32A | 109.2 |
H12A—C12—H12B | 107.9 | C31—C32—H32A | 109.2 |
N3—C13—C12 | 111.9 (3) | C33—C32—H32B | 109.2 |
N3—C13—H13A | 109.2 | C31—C32—H32B | 109.2 |
C12—C13—H13A | 109.2 | H32A—C32—H32B | 107.9 |
N3—C13—H13B | 109.2 | N21—C33—C32 | 113.6 (3) |
C12—C13—H13B | 109.2 | N21—C33—H33A | 108.8 |
H13A—C13—H13B | 107.9 | C32—C33—H33A | 108.8 |
N3—C14—H14A | 109.5 | N21—C33—H33B | 108.8 |
N3—C14—H14B | 109.5 | C32—C33—H33B | 108.8 |
H14A—C14—H14B | 109.5 | H33A—C33—H33B | 107.7 |
N3—C14—H14C | 109.5 | N21—C34—H34A | 109.5 |
H14A—C14—H14C | 109.5 | N21—C34—H34B | 109.5 |
H14B—C14—H14C | 109.5 | H34A—C34—H34B | 109.5 |
N3—C15—H15A | 109.5 | N21—C34—H34C | 109.5 |
N3—C15—H15B | 109.5 | H34A—C34—H34C | 109.5 |
H15A—C15—H15B | 109.5 | H34B—C34—H34C | 109.5 |
N3—C15—H15C | 109.5 | N21—C35—H35A | 109.5 |
H15A—C15—H15C | 109.5 | N21—C35—H35B | 109.5 |
H15B—C15—H15C | 109.5 | H35A—C35—H35B | 109.5 |
B11—O11—B13 | 120.2 (3) | N21—C35—H35C | 109.5 |
B11—O12—B12 | 118.5 (3) | H35A—C35—H35C | 109.5 |
B12—O13—B13 | 123.6 (3) | H35B—C35—H35C | 109.5 |
B11—O14—C16 | 120.2 (3) | O25—C36—C37 | 111.1 (3) |
C21—O15—B12 | 115.2 (3) | O25—C36—H36A | 109.4 |
C26—O16—B13 | 113.9 (2) | C37—C36—H36A | 109.4 |
C20—N11—C18 | 109.6 (3) | O25—C36—H36B | 109.4 |
C20—N11—C19 | 109.9 (3) | C37—C36—H36B | 109.4 |
C18—N11—C19 | 111.6 (3) | H36A—C36—H36B | 108.0 |
C24—N12—C25 | 107.0 (2) | C38—C37—C36 | 111.2 (3) |
C24—N12—C23 | 110.1 (2) | C38—C37—H37A | 109.4 |
C25—N12—C23 | 109.3 (2) | C36—C37—H37A | 109.4 |
C24—N12—B12 | 110.1 (2) | C38—C37—H37B | 109.4 |
C25—N12—B12 | 110.7 (2) | C36—C37—H37B | 109.4 |
C23—N12—B12 | 109.5 (2) | H37A—C37—H37B | 108.0 |
C30—N13—C29 | 108.1 (2) | N22—C38—C37 | 112.4 (2) |
C30—N13—C28 | 108.3 (2) | N22—C38—H38A | 109.1 |
C29—N13—C28 | 110.1 (2) | C37—C38—H38A | 109.1 |
C30—N13—B13 | 111.2 (2) | N22—C38—H38B | 109.1 |
C29—N13—B13 | 110.9 (2) | C37—C38—H38B | 109.1 |
C28—N13—B13 | 108.2 (2) | H38A—C38—H38B | 107.9 |
O11—B11—O12 | 123.8 (3) | N22—C39—H39A | 109.5 |
O11—B11—O14 | 116.0 (3) | N22—C39—H39B | 109.5 |
O12—B11—O14 | 120.2 (3) | H39A—C39—H39B | 109.5 |
O13—B12—O15 | 112.0 (3) | N22—C39—H39C | 109.5 |
O13—B12—O12 | 116.5 (3) | H39A—C39—H39C | 109.5 |
O15—B12—O12 | 112.6 (3) | H39B—C39—H39C | 109.5 |
O13—B12—N12 | 107.1 (3) | N22—C40—H40A | 109.5 |
O15—B12—N12 | 103.7 (2) | N22—C40—H40B | 109.5 |
O12—B12—N12 | 103.4 (2) | H40A—C40—H40B | 109.5 |
O13—B13—O16 | 115.4 (3) | N22—C40—H40C | 109.5 |
O13—B13—O11 | 114.8 (3) | H40A—C40—H40C | 109.5 |
O16—B13—O11 | 108.8 (3) | H40B—C40—H40C | 109.5 |
O13—B13—N13 | 106.8 (3) | O26—C41—C42 | 110.9 (3) |
O16—B13—N13 | 105.2 (2) | O26—C41—H41A | 109.5 |
O11—B13—N13 | 104.7 (2) | C42—C41—H41A | 109.5 |
O14—C16—C17 | 108.4 (3) | O26—C41—H41B | 109.5 |
O14—C16—H16A | 110.0 | C42—C41—H41B | 109.5 |
C17—C16—H16A | 110.0 | H41A—C41—H41B | 108.1 |
O14—C16—H16B | 110.0 | C43—C42—C41 | 111.5 (3) |
C17—C16—H16B | 110.0 | C43—C42—H42A | 109.3 |
H16A—C16—H16B | 108.4 | C41—C42—H42A | 109.3 |
C18—C17—C16 | 114.1 (3) | C43—C42—H42B | 109.3 |
C18—C17—H17A | 108.7 | C41—C42—H42B | 109.3 |
C16—C17—H17A | 108.7 | H42A—C42—H42B | 108.0 |
C18—C17—H17B | 108.7 | N23—C43—C42 | 112.1 (3) |
C16—C17—H17B | 108.7 | N23—C43—H43A | 109.2 |
H17A—C17—H17B | 107.6 | C42—C43—H43A | 109.2 |
N11—C18—C17 | 113.7 (3) | N23—C43—H43B | 109.2 |
N11—C18—H18A | 108.8 | C42—C43—H43B | 109.2 |
C17—C18—H18A | 108.8 | H43A—C43—H43B | 107.9 |
N11—C18—H18B | 108.8 | N23—C44—H44A | 109.5 |
C17—C18—H18B | 108.8 | N23—C44—H44B | 109.5 |
H18A—C18—H18B | 107.7 | H44A—C44—H44B | 109.5 |
N11—C19—H19A | 109.5 | N23—C44—H44C | 109.5 |
N11—C19—H19B | 109.5 | H44A—C44—H44C | 109.5 |
H19A—C19—H19B | 109.5 | H44B—C44—H44C | 109.5 |
N11—C19—H19C | 109.5 | N23—C45—H45A | 109.5 |
H19A—C19—H19C | 109.5 | N23—C45—H45B | 109.5 |
H19B—C19—H19C | 109.5 | H45A—C45—H45B | 109.5 |
N11—C20—H20A | 109.5 | N23—C45—H45C | 109.5 |
N11—C20—H20B | 109.5 | H45A—C45—H45C | 109.5 |
H20A—C20—H20B | 109.5 | H45B—C45—H45C | 109.5 |
B2—O2—B1—O1 | 1.5 (5) | B11—O11—B13—O13 | −9.4 (4) |
B2—O2—B1—O4 | −177.6 (3) | B11—O11—B13—O16 | −140.5 (3) |
B3—O1—B1—O2 | 12.9 (5) | B11—O11—B13—N13 | 107.5 (3) |
B3—O1—B1—O4 | −167.8 (3) | C30—N13—B13—O13 | 54.1 (3) |
C1—O4—B1—O2 | −12.1 (5) | C29—N13—B13—O13 | 174.4 (3) |
C1—O4—B1—O1 | 168.7 (3) | C28—N13—B13—O13 | −64.7 (3) |
B3—O3—B2—O5 | 148.7 (3) | C30—N13—B13—O16 | 177.3 (2) |
B3—O3—B2—O2 | 17.8 (4) | C29—N13—B13—O16 | −62.4 (3) |
B3—O3—B2—N2 | −98.2 (3) | C28—N13—B13—O16 | 58.5 (3) |
C6—O5—B2—O3 | 177.0 (3) | C30—N13—B13—O11 | −68.1 (3) |
C6—O5—B2—O2 | −50.3 (4) | C29—N13—B13—O11 | 52.2 (3) |
C6—O5—B2—N2 | 61.5 (3) | C28—N13—B13—O11 | 173.1 (2) |
B1—O2—B2—O3 | −16.5 (4) | B11—O14—C16—C17 | 178.2 (3) |
B1—O2—B2—O5 | −146.8 (3) | O14—C16—C17—C18 | 172.9 (3) |
B1—O2—B2—N2 | 101.5 (3) | C20—N11—C18—C17 | 177.8 (3) |
C10—N2—B2—O3 | 66.0 (3) | C19—N11—C18—C17 | −60.2 (4) |
C9—N2—B2—O3 | −52.2 (3) | C16—C17—C18—N11 | −57.0 (4) |
C8—N2—B2—O3 | −173.3 (3) | B12—O15—C21—C22 | −65.4 (3) |
C10—N2—B2—O5 | −175.9 (2) | O15—C21—C22—C23 | 55.8 (4) |
C9—N2—B2—O5 | 66.0 (3) | C24—N12—C23—C22 | −68.0 (3) |
C8—N2—B2—O5 | −55.1 (3) | C25—N12—C23—C22 | 174.8 (3) |
C10—N2—B2—O2 | −57.9 (3) | B12—N12—C23—C22 | 53.3 (3) |
C9—N2—B2—O2 | −176.0 (2) | C21—C22—C23—N12 | −53.5 (4) |
C8—N2—B2—O2 | 62.9 (3) | B13—O16—C26—C27 | 62.9 (3) |
B2—O3—B3—O1 | −4.2 (4) | O16—C26—C27—C28 | −53.4 (4) |
B2—O3—B3—O6 | 124.9 (3) | C30—N13—C28—C27 | −175.0 (3) |
B2—O3—B3—N3 | −120.4 (3) | C29—N13—C28—C27 | 67.0 (3) |
B1—O1—B3—O3 | −11.5 (4) | B13—N13—C28—C27 | −54.4 (3) |
B1—O1—B3—O6 | −143.1 (3) | C26—C27—C28—N13 | 52.4 (4) |
B1—O1—B3—N3 | 104.7 (3) | B22—O22—B21—O21 | 0.9 (5) |
C11—O6—B3—O3 | 51.7 (4) | B22—O22—B21—O24 | −178.3 (3) |
C11—O6—B3—O1 | −176.4 (2) | B23—O21—B21—O22 | 2.2 (5) |
C11—O6—B3—N3 | −63.6 (3) | B23—O21—B21—O24 | −178.5 (3) |
C15—N3—B3—O3 | 55.3 (3) | C31—O24—B21—O22 | 8.7 (4) |
C14—N3—B3—O3 | 174.7 (2) | C31—O24—B21—O21 | −170.6 (3) |
C13—N3—B3—O3 | −63.5 (3) | B23—O23—B22—O25 | 149.3 (3) |
C15—N3—B3—O1 | −67.4 (3) | B23—O23—B22—O22 | 18.6 (4) |
C14—N3—B3—O1 | 52.0 (3) | B23—O23—B22—N22 | −96.2 (3) |
C13—N3—B3—O1 | 173.8 (2) | C36—O25—B22—O23 | 178.5 (2) |
C15—N3—B3—O6 | 176.9 (2) | C36—O25—B22—O22 | −49.4 (4) |
C14—N3—B3—O6 | −63.7 (3) | C36—O25—B22—N22 | 61.7 (3) |
C13—N3—B3—O6 | 58.1 (3) | B21—O22—B22—O23 | −10.7 (4) |
B1—O4—C1—C2 | −140.1 (3) | B21—O22—B22—O25 | −140.8 (3) |
O4—C1—C2—C3 | 178.8 (3) | B21—O22—B22—N22 | 107.0 (3) |
C4—N1—C3—C2 | 60.5 (4) | C39—N22—B22—O23 | −53.6 (3) |
C5—N1—C3—C2 | −179.7 (3) | C40—N22—B22—O23 | 66.1 (3) |
C1—C2—C3—N1 | 60.9 (4) | C38—N22—B22—O23 | −174.7 (2) |
B2—O5—C6—C7 | −64.2 (4) | C39—N22—B22—O25 | 65.5 (3) |
O5—C6—C7—C8 | 54.3 (4) | C40—N22—B22—O25 | −174.9 (2) |
C10—N2—C8—C7 | 175.8 (3) | C38—N22—B22—O25 | −55.6 (3) |
C9—N2—C8—C7 | −67.0 (3) | C39—N22—B22—O22 | −176.4 (2) |
B2—N2—C8—C7 | 53.8 (3) | C40—N22—B22—O22 | −56.8 (3) |
C6—C7—C8—N2 | −53.2 (4) | C38—N22—B22—O22 | 62.5 (3) |
B3—O6—C11—C12 | 63.0 (3) | B22—O23—B23—O26 | 112.8 (3) |
O6—C11—C12—C13 | −52.5 (4) | B22—O23—B23—O21 | −15.6 (4) |
C15—N3—C13—C12 | −174.7 (3) | B22—O23—B23—N23 | −131.0 (3) |
C14—N3—C13—C12 | 67.8 (3) | C41—O26—B23—O23 | 52.7 (4) |
B3—N3—C13—C12 | −54.0 (3) | C41—O26—B23—O21 | −176.0 (2) |
C11—C12—C13—N3 | 51.6 (4) | C41—O26—B23—N23 | −64.2 (3) |
B13—O11—B11—O12 | 13.1 (5) | B21—O21—B23—O23 | 4.7 (4) |
B13—O11—B11—O14 | −168.0 (3) | B21—O21—B23—O26 | −126.9 (3) |
B12—O12—B11—O11 | −1.8 (5) | B21—O21—B23—N23 | 121.0 (3) |
B12—O12—B11—O14 | 179.3 (3) | C45—N23—B23—O23 | 54.6 (3) |
C16—O14—B11—O11 | 169.9 (3) | C44—N23—B23—O23 | 174.5 (3) |
C16—O14—B11—O12 | −11.1 (5) | C43—N23—B23—O23 | −65.0 (3) |
B13—O13—B12—O15 | 147.5 (3) | C45—N23—B23—O26 | 177.6 (2) |
B13—O13—B12—O12 | 15.8 (4) | C44—N23—B23—O26 | −62.5 (3) |
B13—O13—B12—N12 | −99.4 (3) | C43—N23—B23—O26 | 58.0 (3) |
C21—O15—B12—O13 | 177.0 (3) | C45—N23—B23—O21 | −67.6 (3) |
C21—O15—B12—O12 | −49.4 (4) | C44—N23—B23—O21 | 52.3 (3) |
C21—O15—B12—N12 | 61.8 (3) | C43—N23—B23—O21 | 172.8 (2) |
B11—O12—B12—O13 | −12.3 (4) | B21—O24—C31—C32 | −162.8 (3) |
B11—O12—B12—O15 | −143.8 (3) | O24—C31—C32—C33 | 68.6 (4) |
B11—O12—B12—N12 | 105.0 (3) | C34—N21—C33—C32 | −58.6 (4) |
C24—N12—B12—O13 | −52.6 (3) | C35—N21—C33—C32 | 179.0 (3) |
C25—N12—B12—O13 | 65.5 (3) | C31—C32—C33—N21 | −172.4 (3) |
C23—N12—B12—O13 | −173.9 (2) | B22—O25—C36—C37 | −63.7 (3) |
C24—N12—B12—O15 | 66.0 (3) | O25—C36—C37—C38 | 54.4 (4) |
C25—N12—B12—O15 | −175.9 (2) | C39—N22—C38—C37 | −67.4 (3) |
C23—N12—B12—O15 | −55.2 (3) | C40—N22—C38—C37 | 175.0 (3) |
C24—N12—B12—O12 | −176.3 (2) | B22—N22—C38—C37 | 54.0 (3) |
C25—N12—B12—O12 | −58.2 (3) | C36—C37—C38—N22 | −53.8 (4) |
C23—N12—B12—O12 | 62.5 (3) | B23—O26—C41—C42 | 64.0 (3) |
B12—O13—B13—O16 | 122.6 (3) | O26—C41—C42—C43 | −53.7 (4) |
B12—O13—B13—O11 | −5.2 (4) | C45—N23—C43—C42 | −175.0 (3) |
B12—O13—B13—N13 | −120.9 (3) | C44—N23—C43—C42 | 67.1 (3) |
C26—O16—B13—O13 | 54.0 (4) | B23—N23—C43—C42 | −53.8 (3) |
C26—O16—B13—O11 | −175.2 (2) | C41—C42—C43—N23 | 52.1 (4) |
C26—O16—B13—N13 | −63.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9C···O5i | 0.98 | 2.54 | 3.477 (4) | 160 |
C13—H13A···O11ii | 0.99 | 2.52 | 3.441 (4) | 155 |
C14—H14A···O11ii | 0.98 | 2.57 | 3.457 (4) | 151 |
C28—H28A···O1ii | 0.99 | 2.53 | 3.450 (4) | 154 |
C29—H29A···O1ii | 0.98 | 2.52 | 3.436 (4) | 155 |
C30—H30C···O6ii | 0.98 | 2.59 | 3.520 (4) | 158 |
C38—H38B···O15iii | 0.99 | 2.43 | 3.345 (4) | 153 |
C39—H39C···O15iii | 0.98 | 2.59 | 3.452 (4) | 148 |
C40—H40A···O13iii | 0.98 | 2.52 | 3.464 (4) | 161 |
C40—H40C···O26 | 0.98 | 2.47 | 3.389 (4) | 156 |
C43—H43A···O21iv | 0.99 | 2.55 | 3.473 (4) | 155 |
C44—H44A···O21iv | 0.98 | 2.55 | 3.456 (4) | 154 |
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) x+1/2, −y+1/2, −z+1; (iii) −x+3/2, y+1/2, z; (iv) x−1/2, −y+3/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C15H36B3N3O6 |
Mr | 386.90 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 113 |
a, b, c (Å) | 10.333 (2), 28.914 (5), 41.642 (8) |
V (Å3) | 12441 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.67 × 0.65 × 0.09 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.855, 1.0 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 105164, 12733, 5839 |
Rint | 0.277 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.070, 0.145, 0.98 |
No. of reflections | 12733 |
No. of parameters | 748 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.28 |
Computer programs: SMART (Bruker, 2001), SMART, SAINT (Bruker, 2001) and SADABS (Sheldrick, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997).
O1—B1 | 1.359 (4) | O4—C1 | 1.435 (4) |
O1—B3 | 1.442 (4) | O5—B2 | 1.446 (4) |
O2—B2 | 1.467 (4) | N2—B2 | 1.721 (4) |
O3—B2 | 1.394 (4) | N3—B3 | 1.685 (4) |
B1—O1—B3 | 120.2 (3) | O3—B2—O2 | 116.2 (3) |
O2—B1—O1 | 123.4 (3) | O5—B2—N2 | 103.7 (2) |
O3—B2—O5 | 111.4 (3) | O3—B3—N3 | 105.6 (2) |
B3—O1—B1—O4 | −167.8 (3) | C19—N11—C18—C17 | −60.2 (4) |
C1—O4—B1—O1 | 168.7 (3) | C16—C17—C18—N11 | −57.0 (4) |
B1—O4—C1—C2 | −140.1 (3) | B23—O21—B21—O24 | −178.5 (3) |
O4—C1—C2—C3 | 178.8 (3) | B21—O24—C31—C32 | −162.8 (3) |
C4—N1—C3—C2 | 60.5 (4) | O24—C31—C32—C33 | 68.6 (4) |
C1—C2—C3—N1 | 60.9 (4) | C34—N21—C33—C32 | −58.6 (4) |
B11—O14—C16—C17 | 178.2 (3) | C31—C32—C33—N21 | −172.4 (3) |
O14—C16—C17—C18 | 172.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9C···O5i | 0.98 | 2.54 | 3.477 (4) | 160 |
C13—H13A···O11ii | 0.99 | 2.52 | 3.441 (4) | 155 |
C14—H14A···O11ii | 0.98 | 2.57 | 3.457 (4) | 151 |
C28—H28A···O1ii | 0.99 | 2.53 | 3.450 (4) | 154 |
C29—H29A···O1ii | 0.98 | 2.52 | 3.436 (4) | 155 |
C30—H30C···O6ii | 0.98 | 2.59 | 3.520 (4) | 158 |
C38—H38B···O15iii | 0.99 | 2.43 | 3.345 (4) | 153 |
C39—H39C···O15iii | 0.98 | 2.59 | 3.452 (4) | 148 |
C40—H40A···O13iii | 0.98 | 2.52 | 3.464 (4) | 161 |
C40—H40C···O26 | 0.98 | 2.47 | 3.389 (4) | 156 |
C43—H43A···O21iv | 0.99 | 2.55 | 3.473 (4) | 155 |
C44—H44A···O21iv | 0.98 | 2.55 | 3.456 (4) | 154 |
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) x+1/2, −y+1/2, −z+1; (iii) −x+3/2, y+1/2, z; (iv) x−1/2, −y+3/2, −z+2. |
This study is part of a programme aimed at investigating boron diolates, aminoalcoholates and alkoxides (Gainsford & Kemmitt, 2005, and references therein). Although borates form a range of diolate complexes (Bachelier & Verchere, 1995; Springsteen & Wang, 2002), structural data are sparse. The Cambridge Structural Database (CSD; Allen, 2002) contains no compounds based on a six-membered B3O3 ring with the boron bound to a tertiary amine in a six-membered ring. The closest examples contain a imino function in the BNC3O ring (CSD refcode DANDEC; Vargas et al., 2004) and five-membered BNOBO ring [a polycyclic condensate of phenyl boronic acid with N-hydroxypiperidine, refcode MOXCOR (Kliegel et al., 2002)]. The title compound, (I), is thus quite novel, and the appearance of three independent copies in the crystal raises some bonding and packing issues, the former through the remarkable internal parameter agreement.
The crystal contains three independent molecules, as shown in Figs. 1–3. Fig. 4 further illustrates that the two bis-chelating ligands and the central B3O3 rings are essentially superimposable, with the monodentate [3-(dimethylamino)propoxy] arm adopting three different conformations (see Table 1). The crystal packing is quite dense (Fig. 5), with the tricyclic units in close relationships, indicating that intermolecular interactions of the C—H···O(B) type dominate (Table 2). By contrast, the [3-(dimethylamino)propoxy] group atoms are at non-interacting (van der Waals) distances between the layers containing the tricyclic units (Fig. 5). The H···O distances are only slightly shorter than the van der Waals contact distance (2.72 Å) implying that localized charge may also be enhancing the interactions.
The dimensions of the the three tricyclic units are essentially identical and so one set of values is presented here (Fig. 1 labels are used). The central B3O3 ring is best described as a flattened boat, with atoms O3, B3, B1 and O2 coplanar [the r.m.s. deviation is ±0.003 (2) Å] and atoms B2 and O1 0.13 (s.u.?)–0.19 (s.u.?) Å from the plane. The B3O3 ring dimensions are remarkably self-consistent [e.g. the trigonal in-plane B—O mean distances are 1.358 (2) Å] and within the ranges noted for a pentaborate (CSPBOR; Fronecke or Frohnecke et al., 1977) and a nonaborate structure (WEHFAQ; Schubert et al., 2000).
The BOC3N rings are in normal chair conformations; atoms B2, N2, C6 and C7 average 0.010 (2) Å from the plane, with atoms O5 and C8 lying 0.645 (4) and 0.635 (4) Å, respectively, from opposite sides of the plane. The B—N lengths found here are within the ranges observed previously for four-coordinate B, for example 1.732 Å within an O2BCN ring (CANXOE; Yalpani & Boese, 1983) and 1.693 Å in WOLLOY (Rico et al., 1999); other longer interaction distances can involve the fused-ring linking bonds [e.g. 1.736 and 1.761 Å in a boratabicyclo(3.3.0)octane structure (YAPGAX; Kliegel et al., 1992)]. Shorter distances are commonly observed in six-membered rings [e.g. in a 1,3,2-oxazaborinane (1.640 Å; Ferguson et al., 1991)] and in non-ring systems [e.g. 1.619 and 1.627 Å in an isobutylamine compound (CEZHUK; Beckett et al., 1999)]. The two B—N lengths in each molecule are consistently different, even though their chemical environments appear identical; the statistical averages (Fig. 1 labels) are 1.723 (7) and 1.678 (5) Å for N2—B2 and N3—B3, respectively. One can have confidence in the B—N difference because of other self-consistencies in the parameters; for example, the equivalent B—O bonds O1—B1 and O2—B1 both average (statistically) as 1.358 (2) Å (with X-ray derived errors of 0.003 Å). As such a difference is statisically significant [being 0.045 (9) Å, compared with refinement standard uncertainities for the difference of 0.006 Å], we attempted to determine its source. In structural terms, the B2—O3 and B3—O3 bonds are also different, with statistical averages of 1.400 (5) and 1.426 (3) Å; these lengths ensure that the O3···N2 and O3···N3 distances are similar.
We determined the relative electronic energies (gas phase) using the Amsterdam Density Function programmes (SCM, 2005), starting initially using the X-ray coordinates. As expected, the B—N distances moved to longer gas-phase values (around 1.75 Å) but the refined models also retained somewhat reduced but significant B—N length differences (around 0.02–03 Å). Using the restraint feature (on the B—N distances only), we also forced the inversion of the B—N distances, and refinement to a mean distance with subsequent release from these states. All calculated relative energies were within 1 kcal mol−1 (the initial molecules 2 and 3 were within 0.1 kcal mol−1). Our conclusions are that the observed X-ray differences reflect small energy changes (much less than those for hydrogen bonds) and that minor model alterations result in final similar energies. Both B—N-distance forced changes gave equivalent energies; refinement from the median values always gave non-equivalent B—N values in the final models, even though the energy gain for this was less than 0.7 kcal mol−1. Finally we generated and calculated the relative electronic energies for three- and one-bis-chelating six-membered BOC3N ring models; both are less stable, by aproximately 7 and 5.5 kcal mol−1 respectively. Thus, ignoring entropy effects, it appears that the most stable entities are those observed in the crystal structure. In summary, the observed difference in the B—N bond lengths in these three compounds is consistent with a small gain in electronic stability.