Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010704468X/gd3147sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010704468X/gd3147Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010704468X/gd3147IIsup3.hkl |
CCDC references: 669173; 669174
To a solution of 2-naphthylamine (3.58 g, 25 mmol) in diethyl ether (30 ml), nBuLi (10 ml, 25 mmol, 2.5 M solution in hexanes) was added dropwise at 273 K. The bright-yellow solution obtained was stirred at room temperature for 2 h and cooled to 263 K. A solution of SiCl4 (1.06 g, 6.25 mmol) in diethyl ether (10 ml) was added dropwise. The solution was allowed to warm to room temperature and stirred for a further period of 12 h. LiCl was removed by filtration and the light-purple solution was subjected to vacuum to give Si(NHnaph)4 as colourless crystals in 95% yield (3.63 g). Recrystallization from toluene gave X-ray quality crystals of (I). Recrystallization from THF provided crystals of (II) solvated with three molecules of THF. Analytical data: m.p. 448 K (decomposition); analysis calculated for C40H32SiN4: C 80.50, H 5.40, N 9.38%; found: C 79.84, H 5.76, N 9.10%; 1H NMR (THF-d8, δ, p.p.m.): 7.66–7.11 (m, 28H, naph), 2.10 (s, 4H, NH); 29Si NMR (THF-d8, δ, p.p.m.): −53.3 (s).
For both structures, H atoms were included in the refinement in geometrically idealized positions, with N—H = 0.88 Å or C—H = 0.95 and 0.99 Å, and with Uiso(H) = 1.2Ueq(C,N). The final difference maps were free of any chemically significant features. A degree of thermal disorder was apparent in the free THF component in structure (II), as judged by the large displacement parameters and the rather short C—C and C—O bonds.
For both compounds, data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C40H32N4Si | F(000) = 1256 |
Mr = 596.79 | Dx = 1.281 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 12258 reflections |
a = 10.695 (2) Å | θ = 3.1–27.5° |
b = 22.718 (4) Å | µ = 0.11 mm−1 |
c = 13.516 (2) Å | T = 173 K |
β = 109.50 (1)° | Prism, colourless |
V = 3095.6 (9) Å3 | 0.30 × 0.28 × 0.22 mm |
Z = 4 |
Nonius KappaCCD area-detector diffractometer | 7035 independent reflections |
Radiation source: fine-focus sealed tube | 5131 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω and ϕ scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −13→13 |
Tmin = 0.967, Tmax = 0.976 | k = −25→29 |
12258 measured reflections | l = −17→17 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.057P)2 + 0.89P] where P = (Fo2 + 2Fc2)/3 |
7035 reflections | (Δ/σ)max < 0.001 |
406 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C40H32N4Si | V = 3095.6 (9) Å3 |
Mr = 596.79 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.695 (2) Å | µ = 0.11 mm−1 |
b = 22.718 (4) Å | T = 173 K |
c = 13.516 (2) Å | 0.30 × 0.28 × 0.22 mm |
β = 109.50 (1)° |
Nonius KappaCCD area-detector diffractometer | 7035 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 5131 reflections with I > 2σ(I) |
Tmin = 0.967, Tmax = 0.976 | Rint = 0.031 |
12258 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.27 e Å−3 |
7035 reflections | Δρmin = −0.30 e Å−3 |
406 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. |
x | y | z | Uiso*/Ueq | ||
Si1 | 0.29985 (4) | 0.160074 (19) | 0.43388 (3) | 0.02735 (12) | |
N1 | 0.32827 (13) | 0.13594 (6) | 0.32323 (10) | 0.0328 (3) | |
H1N | 0.4120 | 0.1362 | 0.3270 | 0.039* | |
N2 | 0.19988 (13) | 0.11643 (6) | 0.47840 (10) | 0.0302 (3) | |
H2N | 0.1249 | 0.1324 | 0.4783 | 0.036* | |
N3 | 0.45137 (13) | 0.15753 (6) | 0.53215 (10) | 0.0303 (3) | |
H3N | 0.4521 | 0.1376 | 0.5882 | 0.036* | |
N4 | 0.22511 (13) | 0.22749 (6) | 0.40681 (10) | 0.0310 (3) | |
H4N | 0.2091 | 0.2405 | 0.3425 | 0.037* | |
C1 | 0.23878 (15) | 0.11579 (7) | 0.22718 (12) | 0.0286 (3) | |
C2 | 0.11403 (16) | 0.13935 (8) | 0.18532 (13) | 0.0350 (4) | |
H2 | 0.0873 | 0.1699 | 0.2220 | 0.042* | |
C3 | 0.02491 (17) | 0.11928 (8) | 0.08923 (14) | 0.0392 (4) | |
H3 | −0.0616 | 0.1357 | 0.0628 | 0.047* | |
C4 | 0.06162 (17) | 0.07650 (8) | 0.03371 (13) | 0.0359 (4) | |
H4 | 0.0014 | 0.0640 | −0.0320 | 0.043* | |
C5 | 0.18850 (16) | 0.05072 (7) | 0.07333 (12) | 0.0313 (4) | |
C6 | 0.22995 (18) | 0.00643 (8) | 0.01651 (15) | 0.0385 (4) | |
H6 | 0.1715 | −0.0055 | −0.0502 | 0.046* | |
C7 | 0.3512 (2) | −0.01899 (8) | 0.05570 (16) | 0.0452 (5) | |
H7 | 0.3770 | −0.0483 | 0.0162 | 0.054* | |
C8 | 0.43865 (19) | −0.00221 (8) | 0.15442 (16) | 0.0449 (4) | |
H8 | 0.5228 | −0.0207 | 0.1821 | 0.054* | |
C9 | 0.40315 (17) | 0.04081 (8) | 0.21122 (14) | 0.0352 (4) | |
H9 | 0.4634 | 0.0517 | 0.2780 | 0.042* | |
C10 | 0.27835 (15) | 0.06922 (7) | 0.17207 (12) | 0.0281 (3) | |
C11 | 0.22285 (15) | 0.05782 (7) | 0.51536 (12) | 0.0293 (3) | |
C12 | 0.30907 (16) | 0.02207 (7) | 0.48686 (14) | 0.0367 (4) | |
H12 | 0.3542 | 0.0372 | 0.4426 | 0.044* | |
C13 | 0.33152 (17) | −0.03649 (8) | 0.52207 (16) | 0.0439 (4) | |
H13 | 0.3918 | −0.0602 | 0.5016 | 0.053* | |
C14 | 0.26781 (18) | −0.05945 (8) | 0.58503 (16) | 0.0447 (5) | |
H14 | 0.2830 | −0.0992 | 0.6074 | 0.054* | |
C15 | 0.17912 (16) | −0.02459 (7) | 0.61744 (13) | 0.0364 (4) | |
C16 | 0.10982 (19) | −0.04722 (9) | 0.68211 (15) | 0.0467 (5) | |
H16 | 0.1261 | −0.0866 | 0.7069 | 0.056* | |
C17 | 0.0210 (2) | −0.01418 (9) | 0.70947 (14) | 0.0483 (5) | |
H17 | −0.0249 | −0.0306 | 0.7522 | 0.058* | |
C18 | −0.00322 (19) | 0.04426 (9) | 0.67476 (14) | 0.0435 (4) | |
H18 | −0.0662 | 0.0672 | 0.6934 | 0.052* | |
C19 | 0.06360 (17) | 0.06827 (8) | 0.61412 (13) | 0.0361 (4) | |
H19 | 0.0480 | 0.1082 | 0.5929 | 0.043* | |
C20 | 0.15517 (15) | 0.03509 (7) | 0.58241 (12) | 0.0299 (3) | |
C21 | 0.57412 (16) | 0.18195 (7) | 0.53765 (13) | 0.0305 (3) | |
C22 | 0.58601 (19) | 0.21404 (8) | 0.45471 (14) | 0.0433 (4) | |
H22 | 0.5103 | 0.2198 | 0.3940 | 0.052* | |
C23 | 0.7079 (2) | 0.23835 (10) | 0.45846 (16) | 0.0568 (6) | |
H23 | 0.7139 | 0.2596 | 0.3997 | 0.068* | |
C24 | 0.8175 (2) | 0.23201 (10) | 0.54457 (17) | 0.0564 (6) | |
H24 | 0.8992 | 0.2489 | 0.5458 | 0.068* | |
C25 | 0.81039 (17) | 0.20032 (7) | 0.63274 (14) | 0.0371 (4) | |
C26 | 0.92191 (18) | 0.19489 (8) | 0.72485 (15) | 0.0423 (4) | |
H26 | 1.0030 | 0.2131 | 0.7277 | 0.051* | |
C27 | 0.91574 (18) | 0.16415 (8) | 0.80956 (14) | 0.0401 (4) | |
H27 | 0.9914 | 0.1616 | 0.8712 | 0.048* | |
C28 | 0.79719 (17) | 0.13622 (8) | 0.80545 (13) | 0.0370 (4) | |
H28 | 0.7934 | 0.1141 | 0.8640 | 0.044* | |
C29 | 0.68662 (16) | 0.14059 (7) | 0.71760 (12) | 0.0303 (3) | |
H29 | 0.6075 | 0.1209 | 0.7159 | 0.036* | |
C30 | 0.68813 (16) | 0.17386 (7) | 0.62939 (12) | 0.0290 (3) | |
C31 | 0.18560 (16) | 0.26510 (7) | 0.47477 (12) | 0.0288 (3) | |
C32 | 0.25929 (18) | 0.26766 (7) | 0.57944 (13) | 0.0368 (4) | |
H32 | 0.3374 | 0.2445 | 0.6054 | 0.044* | |
C33 | 0.2216 (2) | 0.30387 (8) | 0.64927 (14) | 0.0431 (4) | |
H33 | 0.2728 | 0.3039 | 0.7218 | 0.052* | |
C34 | 0.11225 (19) | 0.33885 (8) | 0.61348 (14) | 0.0404 (4) | |
H34 | 0.0889 | 0.3639 | 0.6608 | 0.048* | |
C35 | 0.03324 (17) | 0.33807 (7) | 0.50602 (13) | 0.0320 (4) | |
C36 | −0.08179 (18) | 0.37335 (8) | 0.46750 (14) | 0.0383 (4) | |
H36 | −0.1052 | 0.3987 | 0.5144 | 0.046* | |
C37 | −0.15976 (18) | 0.37182 (8) | 0.36456 (15) | 0.0398 (4) | |
H37 | −0.2359 | 0.3963 | 0.3401 | 0.048* | |
C38 | −0.12719 (17) | 0.33389 (8) | 0.29468 (14) | 0.0381 (4) | |
H38 | −0.1819 | 0.3325 | 0.2230 | 0.046* | |
C39 | −0.01674 (16) | 0.29883 (7) | 0.32948 (13) | 0.0332 (4) | |
H39 | 0.0033 | 0.2731 | 0.2815 | 0.040* | |
C40 | 0.06803 (15) | 0.30012 (7) | 0.43516 (12) | 0.0286 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Si1 | 0.0278 (2) | 0.0284 (2) | 0.0257 (2) | 0.00109 (18) | 0.00871 (17) | 0.00023 (17) |
N1 | 0.0265 (7) | 0.0436 (8) | 0.0283 (7) | 0.0011 (6) | 0.0091 (5) | −0.0030 (6) |
N2 | 0.0280 (7) | 0.0268 (7) | 0.0376 (8) | 0.0035 (5) | 0.0131 (6) | 0.0018 (6) |
N3 | 0.0302 (7) | 0.0335 (7) | 0.0266 (7) | −0.0020 (6) | 0.0087 (5) | 0.0047 (5) |
N4 | 0.0376 (7) | 0.0307 (7) | 0.0252 (7) | 0.0034 (6) | 0.0111 (6) | 0.0026 (5) |
C1 | 0.0292 (8) | 0.0319 (8) | 0.0260 (8) | −0.0011 (7) | 0.0109 (6) | 0.0020 (6) |
C2 | 0.0353 (9) | 0.0355 (9) | 0.0337 (9) | 0.0067 (7) | 0.0108 (7) | −0.0026 (7) |
C3 | 0.0315 (9) | 0.0442 (10) | 0.0376 (9) | 0.0070 (8) | 0.0060 (7) | 0.0005 (8) |
C4 | 0.0330 (9) | 0.0403 (9) | 0.0299 (9) | −0.0028 (7) | 0.0045 (7) | −0.0018 (7) |
C5 | 0.0338 (8) | 0.0292 (8) | 0.0325 (9) | −0.0045 (7) | 0.0133 (7) | 0.0003 (7) |
C6 | 0.0438 (10) | 0.0326 (9) | 0.0427 (10) | −0.0075 (8) | 0.0193 (8) | −0.0076 (7) |
C7 | 0.0511 (11) | 0.0325 (9) | 0.0585 (12) | −0.0007 (8) | 0.0269 (10) | −0.0103 (8) |
C8 | 0.0422 (10) | 0.0377 (10) | 0.0572 (12) | 0.0087 (8) | 0.0199 (9) | 0.0028 (9) |
C9 | 0.0336 (9) | 0.0358 (9) | 0.0367 (9) | 0.0036 (7) | 0.0124 (7) | 0.0023 (7) |
C10 | 0.0299 (8) | 0.0273 (8) | 0.0295 (8) | −0.0015 (6) | 0.0131 (6) | 0.0027 (6) |
C11 | 0.0255 (8) | 0.0269 (8) | 0.0312 (8) | −0.0009 (6) | 0.0039 (6) | −0.0010 (6) |
C12 | 0.0291 (8) | 0.0339 (9) | 0.0471 (10) | 0.0011 (7) | 0.0129 (7) | −0.0010 (8) |
C13 | 0.0310 (9) | 0.0333 (9) | 0.0624 (12) | 0.0069 (8) | 0.0090 (9) | −0.0032 (9) |
C14 | 0.0342 (9) | 0.0296 (9) | 0.0590 (12) | 0.0024 (8) | 0.0007 (8) | 0.0078 (8) |
C15 | 0.0315 (9) | 0.0326 (9) | 0.0362 (9) | −0.0059 (7) | −0.0006 (7) | 0.0040 (7) |
C16 | 0.0471 (11) | 0.0409 (10) | 0.0426 (11) | −0.0102 (9) | 0.0022 (9) | 0.0116 (8) |
C17 | 0.0532 (12) | 0.0554 (12) | 0.0362 (10) | −0.0176 (10) | 0.0148 (9) | 0.0025 (9) |
C18 | 0.0481 (10) | 0.0467 (11) | 0.0398 (10) | −0.0129 (9) | 0.0202 (8) | −0.0099 (8) |
C19 | 0.0390 (9) | 0.0346 (9) | 0.0350 (9) | −0.0068 (7) | 0.0129 (7) | −0.0058 (7) |
C20 | 0.0256 (8) | 0.0309 (8) | 0.0276 (8) | −0.0051 (7) | 0.0014 (6) | −0.0022 (6) |
C21 | 0.0330 (8) | 0.0255 (8) | 0.0327 (8) | −0.0028 (7) | 0.0107 (7) | 0.0004 (7) |
C22 | 0.0437 (10) | 0.0420 (10) | 0.0384 (10) | −0.0086 (8) | 0.0057 (8) | 0.0120 (8) |
C23 | 0.0554 (12) | 0.0594 (13) | 0.0505 (12) | −0.0201 (10) | 0.0111 (10) | 0.0232 (10) |
C24 | 0.0457 (11) | 0.0607 (13) | 0.0583 (13) | −0.0228 (10) | 0.0113 (10) | 0.0168 (10) |
C25 | 0.0365 (9) | 0.0293 (8) | 0.0411 (10) | −0.0079 (7) | 0.0073 (8) | 0.0015 (7) |
C26 | 0.0352 (9) | 0.0363 (10) | 0.0502 (11) | −0.0095 (8) | 0.0071 (8) | −0.0026 (8) |
C27 | 0.0369 (9) | 0.0377 (10) | 0.0371 (10) | 0.0002 (8) | 0.0010 (8) | −0.0035 (8) |
C28 | 0.0399 (9) | 0.0399 (10) | 0.0304 (9) | 0.0055 (8) | 0.0106 (7) | 0.0014 (7) |
C29 | 0.0315 (8) | 0.0308 (8) | 0.0298 (8) | 0.0013 (7) | 0.0119 (7) | −0.0012 (6) |
C30 | 0.0322 (8) | 0.0230 (7) | 0.0306 (8) | −0.0007 (6) | 0.0091 (7) | −0.0022 (6) |
C31 | 0.0346 (8) | 0.0224 (8) | 0.0320 (8) | −0.0043 (6) | 0.0147 (7) | 0.0008 (6) |
C32 | 0.0436 (10) | 0.0303 (9) | 0.0340 (9) | 0.0012 (8) | 0.0095 (8) | −0.0010 (7) |
C33 | 0.0577 (12) | 0.0373 (10) | 0.0310 (9) | −0.0003 (9) | 0.0102 (8) | −0.0056 (8) |
C34 | 0.0547 (11) | 0.0335 (9) | 0.0365 (10) | −0.0035 (8) | 0.0199 (8) | −0.0084 (7) |
C35 | 0.0386 (9) | 0.0238 (8) | 0.0385 (9) | −0.0056 (7) | 0.0195 (7) | −0.0009 (7) |
C36 | 0.0432 (10) | 0.0307 (9) | 0.0485 (11) | −0.0002 (8) | 0.0255 (8) | −0.0031 (8) |
C37 | 0.0357 (9) | 0.0351 (9) | 0.0533 (11) | 0.0032 (8) | 0.0209 (8) | 0.0038 (8) |
C38 | 0.0341 (9) | 0.0398 (10) | 0.0410 (10) | 0.0009 (8) | 0.0132 (8) | 0.0037 (8) |
C39 | 0.0355 (9) | 0.0319 (9) | 0.0353 (9) | −0.0005 (7) | 0.0158 (7) | 0.0003 (7) |
C40 | 0.0335 (8) | 0.0231 (7) | 0.0332 (8) | −0.0056 (6) | 0.0165 (7) | 0.0019 (6) |
Si1—N2 | 1.7082 (13) | C17—C18 | 1.403 (3) |
Si1—N4 | 1.7097 (14) | C17—H17 | 0.9500 |
Si1—N1 | 1.7125 (14) | C18—C19 | 1.368 (2) |
Si1—N3 | 1.7195 (14) | C18—H18 | 0.9500 |
N1—C1 | 1.408 (2) | C19—C20 | 1.411 (2) |
N1—H1N | 0.8800 | C19—H19 | 0.9500 |
N2—C11 | 1.415 (2) | C21—C22 | 1.378 (2) |
N2—H2N | 0.8800 | C21—C30 | 1.431 (2) |
N3—C21 | 1.404 (2) | C22—C23 | 1.401 (3) |
N3—H3N | 0.8800 | C22—H22 | 0.9500 |
N4—C31 | 1.418 (2) | C23—C24 | 1.355 (3) |
N4—H4N | 0.8800 | C23—H23 | 0.9500 |
C1—C2 | 1.372 (2) | C24—C25 | 1.416 (3) |
C1—C10 | 1.436 (2) | C24—H24 | 0.9500 |
C2—C3 | 1.406 (2) | C25—C26 | 1.413 (2) |
C2—H2 | 0.9500 | C25—C30 | 1.426 (2) |
C3—C4 | 1.363 (2) | C26—C27 | 1.361 (3) |
C3—H3 | 0.9500 | C26—H26 | 0.9500 |
C4—C5 | 1.409 (2) | C27—C28 | 1.402 (3) |
C4—H4 | 0.9500 | C27—H27 | 0.9500 |
C5—C10 | 1.423 (2) | C28—C29 | 1.371 (2) |
C5—C6 | 1.423 (2) | C28—H28 | 0.9500 |
C6—C7 | 1.355 (3) | C29—C30 | 1.416 (2) |
C6—H6 | 0.9500 | C29—H29 | 0.9500 |
C7—C8 | 1.403 (3) | C31—C32 | 1.372 (2) |
C7—H7 | 0.9500 | C31—C40 | 1.432 (2) |
C8—C9 | 1.372 (2) | C32—C33 | 1.409 (2) |
C8—H8 | 0.9500 | C32—H32 | 0.9500 |
C9—C10 | 1.417 (2) | C33—C34 | 1.362 (3) |
C9—H9 | 0.9500 | C33—H33 | 0.9500 |
C11—C12 | 1.377 (2) | C34—C35 | 1.416 (2) |
C11—C20 | 1.432 (2) | C34—H34 | 0.9500 |
C12—C13 | 1.406 (3) | C35—C36 | 1.414 (2) |
C12—H12 | 0.9500 | C35—C40 | 1.427 (2) |
C13—C14 | 1.359 (3) | C36—C37 | 1.363 (3) |
C13—H13 | 0.9500 | C36—H36 | 0.9500 |
C14—C15 | 1.413 (3) | C37—C38 | 1.406 (2) |
C14—H14 | 0.9500 | C37—H37 | 0.9500 |
C15—C16 | 1.418 (3) | C38—C39 | 1.371 (2) |
C15—C20 | 1.431 (2) | C38—H38 | 0.9500 |
C16—C17 | 1.355 (3) | C39—C40 | 1.414 (2) |
C16—H16 | 0.9500 | C39—H39 | 0.9500 |
N2—Si1—N4 | 107.00 (7) | C19—C18—C17 | 120.17 (18) |
N2—Si1—N1 | 115.86 (7) | C19—C18—H18 | 119.9 |
N4—Si1—N1 | 107.85 (7) | C17—C18—H18 | 119.9 |
N2—Si1—N3 | 104.34 (7) | C18—C19—C20 | 121.56 (17) |
N4—Si1—N3 | 116.63 (7) | C18—C19—H19 | 119.2 |
N1—Si1—N3 | 105.52 (7) | C20—C19—H19 | 119.2 |
C1—N1—Si1 | 130.19 (11) | C19—C20—C15 | 118.12 (15) |
C1—N1—H1N | 114.9 | C19—C20—C11 | 123.26 (15) |
Si1—N1—H1N | 114.9 | C15—C20—C11 | 118.60 (15) |
C11—N2—Si1 | 127.99 (11) | C22—C21—N3 | 120.29 (15) |
C11—N2—H2N | 116.0 | C22—C21—C30 | 119.30 (15) |
Si1—N2—H2N | 116.0 | N3—C21—C30 | 120.41 (14) |
C21—N3—Si1 | 130.61 (11) | C21—C22—C23 | 121.09 (17) |
C21—N3—H3N | 114.7 | C21—C22—H22 | 119.5 |
Si1—N3—H3N | 114.7 | C23—C22—H22 | 119.5 |
C31—N4—Si1 | 128.33 (11) | C24—C23—C22 | 121.09 (18) |
C31—N4—H4N | 115.8 | C24—C23—H23 | 119.5 |
Si1—N4—H4N | 115.8 | C22—C23—H23 | 119.5 |
C2—C1—N1 | 121.44 (14) | C23—C24—C25 | 120.20 (18) |
C2—C1—C10 | 119.19 (14) | C23—C24—H24 | 119.9 |
N1—C1—C10 | 119.37 (14) | C25—C24—H24 | 119.9 |
C1—C2—C3 | 121.36 (15) | C26—C25—C24 | 121.29 (16) |
C1—C2—H2 | 119.3 | C26—C25—C30 | 119.12 (16) |
C3—C2—H2 | 119.3 | C24—C25—C30 | 119.58 (16) |
C4—C3—C2 | 120.58 (16) | C27—C26—C25 | 121.48 (17) |
C4—C3—H3 | 119.7 | C27—C26—H26 | 119.3 |
C2—C3—H3 | 119.7 | C25—C26—H26 | 119.3 |
C3—C4—C5 | 120.32 (16) | C26—C27—C28 | 119.72 (16) |
C3—C4—H4 | 119.8 | C26—C27—H27 | 120.1 |
C5—C4—H4 | 119.8 | C28—C27—H27 | 120.1 |
C4—C5—C10 | 119.79 (15) | C29—C28—C27 | 120.56 (16) |
C4—C5—C6 | 121.50 (15) | C29—C28—H28 | 119.7 |
C10—C5—C6 | 118.71 (15) | C27—C28—H28 | 119.7 |
C7—C6—C5 | 121.33 (17) | C28—C29—C30 | 121.24 (15) |
C7—C6—H6 | 119.3 | C28—C29—H29 | 119.4 |
C5—C6—H6 | 119.3 | C30—C29—H29 | 119.4 |
C6—C7—C8 | 120.21 (17) | C29—C30—C25 | 117.79 (15) |
C6—C7—H7 | 119.9 | C29—C30—C21 | 123.51 (14) |
C8—C7—H7 | 119.9 | C25—C30—C21 | 118.70 (14) |
C9—C8—C7 | 120.30 (17) | C32—C31—N4 | 120.04 (14) |
C9—C8—H8 | 119.8 | C32—C31—C40 | 119.50 (15) |
C7—C8—H8 | 119.8 | N4—C31—C40 | 120.45 (14) |
C8—C9—C10 | 121.18 (16) | C31—C32—C33 | 121.42 (17) |
C8—C9—H9 | 119.4 | C31—C32—H32 | 119.3 |
C10—C9—H9 | 119.4 | C33—C32—H32 | 119.3 |
C9—C10—C5 | 118.22 (15) | C34—C33—C32 | 120.44 (17) |
C9—C10—C1 | 123.08 (15) | C34—C33—H33 | 119.8 |
C5—C10—C1 | 118.70 (14) | C32—C33—H33 | 119.8 |
C12—C11—N2 | 120.66 (15) | C33—C34—C35 | 120.31 (16) |
C12—C11—C20 | 119.46 (15) | C33—C34—H34 | 119.8 |
N2—C11—C20 | 119.88 (14) | C35—C34—H34 | 119.8 |
C11—C12—C13 | 121.20 (17) | C36—C35—C34 | 121.24 (15) |
C11—C12—H12 | 119.4 | C36—C35—C40 | 119.01 (16) |
C13—C12—H12 | 119.4 | C34—C35—C40 | 119.73 (15) |
C14—C13—C12 | 120.68 (17) | C37—C36—C35 | 121.47 (16) |
C14—C13—H13 | 119.7 | C37—C36—H36 | 119.3 |
C12—C13—H13 | 119.7 | C35—C36—H36 | 119.3 |
C13—C14—C15 | 120.51 (16) | C36—C37—C38 | 119.82 (16) |
C13—C14—H14 | 119.7 | C36—C37—H37 | 120.1 |
C15—C14—H14 | 119.7 | C38—C37—H37 | 120.1 |
C14—C15—C16 | 122.07 (17) | C39—C38—C37 | 120.26 (17) |
C14—C15—C20 | 119.55 (16) | C39—C38—H38 | 119.9 |
C16—C15—C20 | 118.36 (17) | C37—C38—H38 | 119.9 |
C17—C16—C15 | 121.71 (17) | C38—C39—C40 | 121.53 (15) |
C17—C16—H16 | 119.1 | C38—C39—H39 | 119.2 |
C15—C16—H16 | 119.1 | C40—C39—H39 | 119.2 |
C16—C17—C18 | 120.06 (17) | C39—C40—C35 | 117.89 (15) |
C16—C17—H17 | 120.0 | C39—C40—C31 | 123.57 (14) |
C18—C17—H17 | 120.0 | C35—C40—C31 | 118.54 (15) |
N2—Si1—N1—C1 | 48.19 (17) | C14—C15—C20—C11 | −0.2 (2) |
N4—Si1—N1—C1 | −71.64 (16) | C16—C15—C20—C11 | −178.75 (15) |
N3—Si1—N1—C1 | 163.04 (14) | C12—C11—C20—C19 | −178.93 (15) |
N4—Si1—N2—C11 | −176.70 (13) | N2—C11—C20—C19 | 0.6 (2) |
N1—Si1—N2—C11 | 63.01 (15) | C12—C11—C20—C15 | −0.3 (2) |
N3—Si1—N2—C11 | −52.51 (15) | N2—C11—C20—C15 | 179.20 (14) |
N2—Si1—N3—C21 | 175.89 (14) | Si1—N3—C21—C22 | −0.1 (2) |
N4—Si1—N3—C21 | −66.35 (16) | Si1—N3—C21—C30 | 179.84 (12) |
N1—Si1—N3—C21 | 53.33 (16) | N3—C21—C22—C23 | −179.49 (18) |
N2—Si1—N4—C31 | 56.26 (15) | C30—C21—C22—C23 | 0.6 (3) |
N1—Si1—N4—C31 | −178.45 (13) | C21—C22—C23—C24 | −1.3 (3) |
N3—Si1—N4—C31 | −60.03 (15) | C22—C23—C24—C25 | 0.2 (4) |
Si1—N1—C1—C2 | 35.2 (2) | C23—C24—C25—C26 | −177.7 (2) |
Si1—N1—C1—C10 | −144.35 (13) | C23—C24—C25—C30 | 1.6 (3) |
N1—C1—C2—C3 | 179.81 (15) | C24—C25—C26—C27 | −179.60 (19) |
C10—C1—C2—C3 | −0.7 (2) | C30—C25—C26—C27 | 1.2 (3) |
C1—C2—C3—C4 | −1.5 (3) | C25—C26—C27—C28 | 1.1 (3) |
C2—C3—C4—C5 | 1.6 (3) | C26—C27—C28—C29 | −1.3 (3) |
C3—C4—C5—C10 | 0.4 (2) | C27—C28—C29—C30 | −0.8 (3) |
C3—C4—C5—C6 | −179.31 (16) | C28—C29—C30—C25 | 3.1 (2) |
C4—C5—C6—C7 | −178.83 (17) | C28—C29—C30—C21 | −177.21 (15) |
C10—C5—C6—C7 | 1.5 (2) | C26—C25—C30—C29 | −3.2 (2) |
C5—C6—C7—C8 | 0.5 (3) | C24—C25—C30—C29 | 177.54 (17) |
C6—C7—C8—C9 | −1.2 (3) | C26—C25—C30—C21 | 177.07 (16) |
C7—C8—C9—C10 | 0.0 (3) | C24—C25—C30—C21 | −2.2 (3) |
C8—C9—C10—C5 | 1.9 (2) | C22—C21—C30—C29 | −178.59 (16) |
C8—C9—C10—C1 | −177.88 (16) | N3—C21—C30—C29 | 1.5 (2) |
C4—C5—C10—C9 | 177.69 (15) | C22—C21—C30—C25 | 1.1 (2) |
C6—C5—C10—C9 | −2.6 (2) | N3—C21—C30—C25 | −178.80 (14) |
C4—C5—C10—C1 | −2.5 (2) | Si1—N4—C31—C32 | 34.5 (2) |
C6—C5—C10—C1 | 177.21 (14) | Si1—N4—C31—C40 | −144.82 (12) |
C2—C1—C10—C9 | −177.57 (15) | N4—C31—C32—C33 | −179.00 (15) |
N1—C1—C10—C9 | 2.0 (2) | C40—C31—C32—C33 | 0.3 (2) |
C2—C1—C10—C5 | 2.6 (2) | C31—C32—C33—C34 | −2.0 (3) |
N1—C1—C10—C5 | −177.85 (14) | C32—C33—C34—C35 | 1.6 (3) |
Si1—N2—C11—C12 | −22.5 (2) | C33—C34—C35—C36 | 179.02 (17) |
Si1—N2—C11—C20 | 158.05 (12) | C33—C34—C35—C40 | 0.4 (2) |
N2—C11—C12—C13 | −179.23 (15) | C34—C35—C36—C37 | −178.57 (16) |
C20—C11—C12—C13 | 0.3 (2) | C40—C35—C36—C37 | 0.0 (2) |
C11—C12—C13—C14 | 0.3 (3) | C35—C36—C37—C38 | 0.9 (3) |
C12—C13—C14—C15 | −0.9 (3) | C36—C37—C38—C39 | −0.5 (3) |
C13—C14—C15—C16 | 179.28 (17) | C37—C38—C39—C40 | −0.8 (2) |
C13—C14—C15—C20 | 0.8 (3) | C38—C39—C40—C35 | 1.7 (2) |
C14—C15—C16—C17 | −177.36 (17) | C38—C39—C40—C31 | −178.91 (15) |
C20—C15—C16—C17 | 1.1 (3) | C36—C35—C40—C39 | −1.3 (2) |
C15—C16—C17—C18 | −0.8 (3) | C34—C35—C40—C39 | 177.30 (14) |
C16—C17—C18—C19 | −0.7 (3) | C36—C35—C40—C31 | 179.27 (14) |
C17—C18—C19—C20 | 1.8 (3) | C34—C35—C40—C31 | −2.1 (2) |
C18—C19—C20—C15 | −1.4 (2) | C32—C31—C40—C39 | −177.62 (15) |
C18—C19—C20—C11 | 177.26 (16) | N4—C31—C40—C39 | 1.7 (2) |
C14—C15—C20—C19 | 178.48 (15) | C32—C31—C40—C35 | 1.7 (2) |
C16—C15—C20—C19 | 0.0 (2) | N4—C31—C40—C35 | −178.97 (13) |
C40H32N4Si·3C4H8O | F(000) = 1736 |
Mr = 813.10 | Dx = 1.191 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 17657 reflections |
a = 21.048 (7) Å | θ = 3.0–27.5° |
b = 14.672 (7) Å | µ = 0.10 mm−1 |
c = 15.160 (9) Å | T = 173 K |
β = 104.46 (2)° | Block, colourless |
V = 4533 (4) Å3 | 0.10 × 0.08 × 0.06 mm |
Z = 4 |
Nonius KappaCCD area-detector diffractometer | 9976 independent reflections |
Radiation source: fine-focus sealed tube | 3609 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.175 |
ω and ϕ scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −27→27 |
Tmin = 0.990, Tmax = 0.994 | k = −17→18 |
17657 measured reflections | l = −19→19 |
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)] = 0.078 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.230 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.092P)2] where P = (Fo2 + 2Fc2)/3 |
9976 reflections | (Δ/σ)max = 0.005 |
544 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C40H32N4Si·3C4H8O | V = 4533 (4) Å3 |
Mr = 813.10 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 21.048 (7) Å | µ = 0.10 mm−1 |
b = 14.672 (7) Å | T = 173 K |
c = 15.160 (9) Å | 0.10 × 0.08 × 0.06 mm |
β = 104.46 (2)° |
Nonius KappaCCD area-detector diffractometer | 9976 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 3609 reflections with I > 2σ(I) |
Tmin = 0.990, Tmax = 0.994 | Rint = 0.175 |
17657 measured reflections |
R[F2 > 2σ(F2)] = 0.078 | 0 restraints |
wR(F2) = 0.230 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.33 e Å−3 |
9976 reflections | Δρmin = −0.24 e Å−3 |
544 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. |
x | y | z | Uiso*/Ueq | ||
Si1 | 0.28123 (5) | 0.51154 (7) | 0.05615 (6) | 0.0490 (3) | |
N1 | 0.32355 (14) | 0.6098 (2) | 0.05040 (19) | 0.0528 (8) | |
H1N | 0.3136 | 0.6559 | 0.0817 | 0.063* | |
N2 | 0.23661 (14) | 0.4762 (2) | −0.04896 (18) | 0.0557 (8) | |
H2N | 0.2471 | 0.4220 | −0.0658 | 0.067* | |
N3 | 0.32673 (14) | 0.4156 (2) | 0.09088 (18) | 0.0530 (8) | |
H3N | 0.3162 | 0.3688 | 0.0537 | 0.064* | |
N4 | 0.23633 (14) | 0.5439 (2) | 0.13023 (19) | 0.0548 (8) | |
H4N | 0.2422 | 0.6001 | 0.1508 | 0.066* | |
C1 | 0.37212 (16) | 0.6286 (3) | 0.0030 (2) | 0.0478 (9) | |
C2 | 0.40571 (18) | 0.5587 (3) | −0.0253 (2) | 0.0615 (11) | |
H2 | 0.3953 | 0.4973 | −0.0146 | 0.074* | |
C3 | 0.4551 (2) | 0.5771 (4) | −0.0697 (3) | 0.0697 (12) | |
H3 | 0.4776 | 0.5280 | −0.0893 | 0.084* | |
C4 | 0.4712 (2) | 0.6639 (4) | −0.0852 (3) | 0.0675 (12) | |
H4 | 0.5062 | 0.6747 | −0.1131 | 0.081* | |
C5 | 0.43725 (19) | 0.7382 (3) | −0.0607 (2) | 0.0574 (11) | |
C6 | 0.4512 (2) | 0.8291 (4) | −0.0793 (3) | 0.0742 (13) | |
H6 | 0.4863 | 0.8411 | −0.1066 | 0.089* | |
C7 | 0.4159 (2) | 0.8998 (4) | −0.0593 (3) | 0.0818 (14) | |
H7 | 0.4260 | 0.9606 | −0.0725 | 0.098* | |
C8 | 0.3642 (2) | 0.8821 (3) | −0.0191 (3) | 0.0776 (13) | |
H8 | 0.3385 | 0.9312 | −0.0063 | 0.093* | |
C9 | 0.35026 (19) | 0.7959 (3) | 0.0020 (3) | 0.0591 (11) | |
H9 | 0.3155 | 0.7861 | 0.0306 | 0.071* | |
C10 | 0.38575 (17) | 0.7205 (3) | −0.0173 (2) | 0.0476 (9) | |
C11 | 0.18609 (18) | 0.5204 (3) | −0.1120 (2) | 0.0541 (10) | |
C12 | 0.1578 (2) | 0.5978 (3) | −0.0898 (3) | 0.0714 (12) | |
H12 | 0.1732 | 0.6231 | −0.0307 | 0.086* | |
C13 | 0.1056 (2) | 0.6412 (4) | −0.1534 (4) | 0.0832 (14) | |
H13 | 0.0866 | 0.6952 | −0.1366 | 0.100* | |
C14 | 0.0827 (2) | 0.6062 (4) | −0.2377 (3) | 0.0860 (15) | |
H14 | 0.0478 | 0.6361 | −0.2797 | 0.103* | |
C15 | 0.1098 (2) | 0.5261 (4) | −0.2644 (3) | 0.0689 (12) | |
C16 | 0.0865 (2) | 0.4889 (4) | −0.3529 (3) | 0.0864 (16) | |
H16 | 0.0504 | 0.5169 | −0.3945 | 0.104* | |
C17 | 0.1147 (3) | 0.4139 (5) | −0.3793 (3) | 0.0930 (17) | |
H17 | 0.0987 | 0.3900 | −0.4390 | 0.112* | |
C18 | 0.1676 (3) | 0.3719 (4) | −0.3181 (3) | 0.0842 (14) | |
H18 | 0.1872 | 0.3193 | −0.3364 | 0.101* | |
C19 | 0.1911 (2) | 0.4060 (3) | −0.2321 (3) | 0.0642 (12) | |
H19 | 0.2274 | 0.3770 | −0.1920 | 0.077* | |
C20 | 0.16273 (18) | 0.4826 (3) | −0.2018 (3) | 0.0567 (10) | |
C21 | 0.37803 (17) | 0.3984 (3) | 0.1685 (2) | 0.0481 (9) | |
C22 | 0.41809 (19) | 0.4665 (3) | 0.2116 (3) | 0.0612 (11) | |
H22 | 0.4098 | 0.5277 | 0.1914 | 0.073* | |
C23 | 0.4719 (2) | 0.4468 (4) | 0.2862 (3) | 0.0680 (12) | |
H23 | 0.4988 | 0.4952 | 0.3161 | 0.082* | |
C24 | 0.4859 (2) | 0.3594 (4) | 0.3158 (3) | 0.0715 (13) | |
H24 | 0.5233 | 0.3474 | 0.3644 | 0.086* | |
C25 | 0.4458 (2) | 0.2883 (3) | 0.2753 (3) | 0.0620 (11) | |
C26 | 0.4576 (3) | 0.1958 (4) | 0.3050 (3) | 0.0830 (15) | |
H26 | 0.4949 | 0.1823 | 0.3532 | 0.100* | |
C27 | 0.4178 (3) | 0.1282 (4) | 0.2670 (4) | 0.0965 (17) | |
H27 | 0.4275 | 0.0674 | 0.2876 | 0.116* | |
C28 | 0.3619 (3) | 0.1462 (3) | 0.1971 (3) | 0.0872 (15) | |
H28 | 0.3330 | 0.0981 | 0.1712 | 0.105* | |
C29 | 0.3489 (2) | 0.2328 (3) | 0.1662 (3) | 0.0664 (11) | |
H29 | 0.3106 | 0.2440 | 0.1190 | 0.080* | |
C30 | 0.38994 (18) | 0.3064 (3) | 0.2016 (2) | 0.0518 (10) | |
C31 | 0.19070 (17) | 0.4907 (3) | 0.1624 (2) | 0.0519 (10) | |
C32 | 0.1647 (2) | 0.4133 (3) | 0.1183 (3) | 0.0666 (12) | |
H32 | 0.1777 | 0.3946 | 0.0654 | 0.080* | |
C33 | 0.1188 (2) | 0.3603 (3) | 0.1497 (3) | 0.0810 (14) | |
H33 | 0.1023 | 0.3057 | 0.1188 | 0.097* | |
C34 | 0.0982 (2) | 0.3867 (4) | 0.2231 (3) | 0.0808 (14) | |
H34 | 0.0664 | 0.3512 | 0.2426 | 0.097* | |
C35 | 0.12315 (19) | 0.4660 (4) | 0.2709 (3) | 0.0696 (12) | |
C36 | 0.1035 (3) | 0.4954 (5) | 0.3487 (4) | 0.0991 (18) | |
H36 | 0.0714 | 0.4608 | 0.3684 | 0.119* | |
C37 | 0.1281 (3) | 0.5699 (5) | 0.3959 (4) | 0.108 (2) | |
H37 | 0.1141 | 0.5866 | 0.4485 | 0.129* | |
C38 | 0.1749 (2) | 0.6237 (4) | 0.3677 (3) | 0.0875 (15) | |
H38 | 0.1919 | 0.6774 | 0.4001 | 0.105* | |
C39 | 0.1953 (2) | 0.5971 (3) | 0.2927 (3) | 0.0700 (12) | |
H39 | 0.2275 | 0.6327 | 0.2743 | 0.084* | |
C40 | 0.17071 (18) | 0.5193 (3) | 0.2420 (2) | 0.0548 (10) | |
O1 | 0.26917 (14) | 0.7434 (2) | 0.16730 (17) | 0.0650 (8) | |
C41 | 0.2188 (2) | 0.8099 (4) | 0.1416 (3) | 0.0827 (14) | |
H41A | 0.1882 | 0.8062 | 0.1816 | 0.099* | |
H41B | 0.1936 | 0.8003 | 0.0778 | 0.099* | |
C42 | 0.2522 (3) | 0.9008 (4) | 0.1516 (4) | 0.0941 (16) | |
H42A | 0.2652 | 0.9179 | 0.0954 | 0.113* | |
H42B | 0.2236 | 0.9490 | 0.1664 | 0.113* | |
C43 | 0.3106 (4) | 0.8852 (5) | 0.2284 (5) | 0.137 (2) | |
H43A | 0.3032 | 0.9108 | 0.2855 | 0.164* | |
H43B | 0.3497 | 0.9149 | 0.2160 | 0.164* | |
C44 | 0.3205 (3) | 0.7846 (5) | 0.2371 (3) | 0.1086 (19) | |
H44A | 0.3641 | 0.7678 | 0.2284 | 0.130* | |
H44B | 0.3178 | 0.7637 | 0.2981 | 0.130* | |
O2 | 0.27750 (15) | 0.2736 (2) | −0.05574 (18) | 0.0701 (8) | |
C45 | 0.3349 (3) | 0.2416 (4) | −0.0814 (4) | 0.1079 (19) | |
H45A | 0.3751 | 0.2618 | −0.0365 | 0.129* | |
H45B | 0.3359 | 0.2659 | −0.1420 | 0.129* | |
C46 | 0.3312 (6) | 0.1419 (5) | −0.0840 (6) | 0.174 (4) | |
H46A | 0.3689 | 0.1154 | −0.0387 | 0.209* | |
H46B | 0.3322 | 0.1193 | −0.1452 | 0.209* | |
C47 | 0.2689 (4) | 0.1159 (4) | −0.0626 (6) | 0.151 (3) | |
H47A | 0.2447 | 0.0710 | −0.1072 | 0.181* | |
H47B | 0.2772 | 0.0892 | −0.0008 | 0.181* | |
C48 | 0.2314 (3) | 0.2015 (4) | −0.0677 (4) | 0.1003 (17) | |
H48A | 0.1993 | 0.2067 | −0.1276 | 0.120* | |
H48B | 0.2073 | 0.2032 | −0.0194 | 0.120* | |
O3 | 0.0309 (2) | 0.2568 (3) | 0.4151 (3) | 0.1283 (14) | |
C49 | −0.0232 (4) | 0.2319 (6) | 0.4485 (5) | 0.134 (2) | |
H49A | −0.0625 | 0.2666 | 0.4165 | 0.160* | |
H49B | −0.0142 | 0.2457 | 0.5144 | 0.160* | |
C50 | −0.0343 (4) | 0.1354 (7) | 0.4334 (6) | 0.170 (4) | |
H50A | −0.0797 | 0.1242 | 0.3971 | 0.204* | |
H50B | −0.0278 | 0.1030 | 0.4922 | 0.204* | |
C51 | 0.0127 (4) | 0.1035 (6) | 0.3843 (6) | 0.163 (3) | |
H51A | 0.0418 | 0.0565 | 0.4201 | 0.195* | |
H51B | −0.0103 | 0.0770 | 0.3248 | 0.195* | |
C52 | 0.0492 (4) | 0.1812 (5) | 0.3716 (6) | 0.146 (3) | |
H52A | 0.0966 | 0.1691 | 0.3965 | 0.175* | |
H52B | 0.0417 | 0.1940 | 0.3057 | 0.175* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Si1 | 0.0533 (6) | 0.0435 (7) | 0.0515 (6) | 0.0029 (5) | 0.0156 (4) | 0.0003 (5) |
N1 | 0.0575 (18) | 0.042 (2) | 0.0681 (19) | 0.0045 (16) | 0.0319 (15) | 0.0016 (15) |
N2 | 0.063 (2) | 0.047 (2) | 0.0535 (18) | 0.0095 (16) | 0.0071 (15) | −0.0027 (15) |
N3 | 0.0624 (19) | 0.041 (2) | 0.0497 (17) | 0.0044 (15) | 0.0035 (15) | −0.0040 (14) |
N4 | 0.0639 (19) | 0.043 (2) | 0.0640 (19) | −0.0101 (16) | 0.0280 (15) | −0.0054 (15) |
C1 | 0.044 (2) | 0.057 (3) | 0.0418 (19) | 0.0014 (19) | 0.0109 (16) | −0.0004 (18) |
C2 | 0.062 (2) | 0.056 (3) | 0.073 (3) | 0.005 (2) | 0.029 (2) | −0.007 (2) |
C3 | 0.068 (3) | 0.072 (4) | 0.076 (3) | 0.012 (3) | 0.031 (2) | −0.006 (3) |
C4 | 0.059 (3) | 0.085 (4) | 0.067 (3) | 0.004 (3) | 0.030 (2) | −0.002 (2) |
C5 | 0.054 (2) | 0.073 (3) | 0.047 (2) | 0.001 (2) | 0.0165 (17) | 0.005 (2) |
C6 | 0.079 (3) | 0.074 (4) | 0.079 (3) | −0.005 (3) | 0.037 (2) | 0.017 (3) |
C7 | 0.097 (4) | 0.060 (3) | 0.097 (3) | −0.003 (3) | 0.040 (3) | 0.021 (3) |
C8 | 0.092 (3) | 0.060 (3) | 0.092 (3) | 0.017 (3) | 0.044 (3) | 0.018 (3) |
C9 | 0.067 (3) | 0.048 (3) | 0.070 (3) | 0.007 (2) | 0.032 (2) | 0.013 (2) |
C10 | 0.050 (2) | 0.051 (3) | 0.042 (2) | 0.0018 (19) | 0.0134 (16) | 0.0073 (17) |
C11 | 0.053 (2) | 0.053 (3) | 0.055 (2) | 0.006 (2) | 0.0118 (18) | 0.010 (2) |
C12 | 0.075 (3) | 0.067 (3) | 0.071 (3) | 0.015 (3) | 0.015 (2) | 0.006 (2) |
C13 | 0.072 (3) | 0.083 (4) | 0.098 (4) | 0.029 (3) | 0.028 (3) | 0.015 (3) |
C14 | 0.060 (3) | 0.112 (5) | 0.083 (4) | 0.017 (3) | 0.014 (2) | 0.026 (3) |
C15 | 0.058 (3) | 0.085 (4) | 0.065 (3) | 0.003 (3) | 0.017 (2) | 0.018 (3) |
C16 | 0.068 (3) | 0.118 (5) | 0.066 (3) | −0.006 (3) | 0.002 (2) | 0.017 (3) |
C17 | 0.091 (4) | 0.118 (5) | 0.063 (3) | −0.020 (4) | 0.008 (3) | −0.007 (3) |
C18 | 0.106 (4) | 0.074 (4) | 0.069 (3) | −0.014 (3) | 0.015 (3) | −0.005 (3) |
C19 | 0.076 (3) | 0.062 (3) | 0.052 (2) | −0.007 (2) | 0.010 (2) | 0.003 (2) |
C20 | 0.050 (2) | 0.059 (3) | 0.061 (2) | −0.004 (2) | 0.0134 (19) | 0.012 (2) |
C21 | 0.051 (2) | 0.044 (3) | 0.051 (2) | 0.0022 (19) | 0.0180 (18) | 0.0002 (18) |
C22 | 0.064 (3) | 0.060 (3) | 0.061 (2) | 0.000 (2) | 0.017 (2) | −0.004 (2) |
C23 | 0.063 (3) | 0.078 (4) | 0.064 (3) | −0.014 (3) | 0.017 (2) | −0.018 (2) |
C24 | 0.061 (3) | 0.089 (4) | 0.062 (3) | 0.005 (3) | 0.010 (2) | 0.000 (3) |
C25 | 0.060 (3) | 0.076 (3) | 0.051 (2) | 0.014 (2) | 0.0171 (19) | 0.005 (2) |
C26 | 0.092 (4) | 0.085 (4) | 0.069 (3) | 0.035 (3) | 0.015 (3) | 0.023 (3) |
C27 | 0.142 (5) | 0.063 (4) | 0.082 (4) | 0.030 (4) | 0.023 (4) | 0.019 (3) |
C28 | 0.128 (4) | 0.052 (3) | 0.075 (3) | −0.004 (3) | 0.012 (3) | 0.005 (3) |
C29 | 0.090 (3) | 0.048 (3) | 0.057 (2) | 0.000 (2) | 0.011 (2) | 0.007 (2) |
C30 | 0.058 (2) | 0.053 (3) | 0.046 (2) | 0.008 (2) | 0.0165 (18) | 0.0026 (19) |
C31 | 0.048 (2) | 0.048 (3) | 0.059 (2) | −0.001 (2) | 0.0119 (17) | 0.009 (2) |
C32 | 0.064 (3) | 0.059 (3) | 0.078 (3) | −0.008 (2) | 0.021 (2) | 0.000 (2) |
C33 | 0.061 (3) | 0.067 (4) | 0.110 (4) | −0.015 (2) | 0.012 (3) | 0.001 (3) |
C34 | 0.062 (3) | 0.087 (4) | 0.096 (4) | −0.018 (3) | 0.024 (3) | 0.016 (3) |
C35 | 0.053 (2) | 0.089 (4) | 0.069 (3) | 0.000 (3) | 0.019 (2) | 0.016 (3) |
C36 | 0.084 (3) | 0.137 (6) | 0.088 (4) | −0.010 (4) | 0.043 (3) | 0.016 (4) |
C37 | 0.098 (4) | 0.156 (7) | 0.085 (4) | 0.001 (4) | 0.052 (3) | 0.000 (4) |
C38 | 0.096 (3) | 0.107 (4) | 0.066 (3) | −0.001 (3) | 0.033 (3) | −0.014 (3) |
C39 | 0.071 (3) | 0.083 (4) | 0.061 (3) | 0.002 (3) | 0.025 (2) | 0.007 (2) |
C40 | 0.053 (2) | 0.056 (3) | 0.055 (2) | −0.001 (2) | 0.0131 (18) | 0.010 (2) |
O1 | 0.0749 (18) | 0.057 (2) | 0.0645 (17) | −0.0036 (16) | 0.0196 (14) | −0.0053 (14) |
C41 | 0.074 (3) | 0.079 (4) | 0.099 (3) | 0.008 (3) | 0.027 (3) | −0.005 (3) |
C42 | 0.116 (4) | 0.058 (4) | 0.123 (4) | 0.009 (3) | 0.056 (4) | −0.007 (3) |
C43 | 0.171 (7) | 0.081 (5) | 0.140 (5) | −0.021 (5) | 0.003 (5) | −0.046 (4) |
C44 | 0.116 (4) | 0.112 (5) | 0.077 (3) | −0.016 (4) | −0.014 (3) | 0.000 (3) |
O2 | 0.084 (2) | 0.0517 (19) | 0.0732 (18) | 0.0024 (17) | 0.0166 (15) | −0.0100 (15) |
C45 | 0.126 (5) | 0.095 (5) | 0.125 (4) | 0.021 (4) | 0.074 (4) | 0.012 (4) |
C46 | 0.270 (11) | 0.073 (5) | 0.245 (9) | 0.045 (6) | 0.186 (9) | 0.018 (5) |
C47 | 0.157 (6) | 0.052 (4) | 0.207 (8) | 0.002 (4) | −0.025 (6) | −0.018 (4) |
C48 | 0.097 (4) | 0.082 (4) | 0.107 (4) | −0.009 (3) | −0.002 (3) | −0.003 (3) |
O3 | 0.116 (3) | 0.098 (4) | 0.177 (4) | −0.006 (3) | 0.050 (3) | 0.007 (3) |
C49 | 0.106 (5) | 0.146 (7) | 0.154 (6) | 0.026 (5) | 0.041 (4) | 0.019 (5) |
C50 | 0.139 (6) | 0.185 (9) | 0.211 (8) | −0.087 (6) | 0.091 (6) | −0.080 (7) |
C51 | 0.172 (8) | 0.125 (7) | 0.207 (8) | −0.050 (6) | 0.079 (6) | −0.054 (6) |
C52 | 0.177 (7) | 0.090 (6) | 0.209 (7) | 0.001 (5) | 0.118 (6) | 0.000 (5) |
Si1—N4 | 1.706 (3) | C28—C29 | 1.357 (6) |
Si1—N1 | 1.709 (3) | C28—H28 | 0.9500 |
Si1—N3 | 1.710 (3) | C29—C30 | 1.402 (5) |
Si1—N2 | 1.715 (3) | C29—H29 | 0.9500 |
N1—C1 | 1.415 (4) | C31—C32 | 1.361 (5) |
N1—H1N | 0.8800 | C31—C40 | 1.437 (5) |
N2—C11 | 1.399 (4) | C32—C33 | 1.412 (6) |
N2—H2N | 0.8800 | C32—H32 | 0.9500 |
N3—C21 | 1.408 (4) | C33—C34 | 1.349 (6) |
N3—H3N | 0.8800 | C33—H33 | 0.9500 |
N4—C31 | 1.416 (4) | C34—C35 | 1.401 (6) |
N4—H4N | 0.8800 | C34—H34 | 0.9500 |
C1—C2 | 1.374 (5) | C35—C36 | 1.411 (7) |
C1—C10 | 1.428 (5) | C35—C40 | 1.423 (6) |
C2—C3 | 1.399 (5) | C36—C37 | 1.339 (8) |
C2—H2 | 0.9500 | C36—H36 | 0.9500 |
C3—C4 | 1.353 (6) | C37—C38 | 1.408 (7) |
C3—H3 | 0.9500 | C37—H37 | 0.9500 |
C4—C5 | 1.404 (6) | C38—C39 | 1.369 (5) |
C4—H4 | 0.9500 | C38—H38 | 0.9500 |
C5—C6 | 1.408 (6) | C39—C40 | 1.400 (6) |
C5—C10 | 1.425 (5) | C39—H39 | 0.9500 |
C6—C7 | 1.354 (6) | O1—C41 | 1.422 (5) |
C6—H6 | 0.9500 | O1—C44 | 1.442 (5) |
C7—C8 | 1.397 (6) | C41—C42 | 1.497 (6) |
C7—H7 | 0.9500 | C41—H41A | 0.9900 |
C8—C9 | 1.354 (6) | C41—H41B | 0.9900 |
C8—H8 | 0.9500 | C42—C43 | 1.485 (8) |
C9—C10 | 1.406 (5) | C42—H42A | 0.9900 |
C9—H9 | 0.9500 | C42—H42B | 0.9900 |
C11—C12 | 1.363 (5) | C43—C44 | 1.492 (8) |
C11—C20 | 1.439 (5) | C43—H43A | 0.9900 |
C12—C13 | 1.419 (6) | C43—H43B | 0.9900 |
C12—H12 | 0.9500 | C44—H44A | 0.9900 |
C13—C14 | 1.349 (6) | C44—H44B | 0.9900 |
C13—H13 | 0.9500 | O2—C48 | 1.416 (6) |
C14—C15 | 1.409 (6) | O2—C45 | 1.437 (5) |
C14—H14 | 0.9500 | C45—C46 | 1.465 (8) |
C15—C16 | 1.418 (6) | C45—H45A | 0.9900 |
C15—C20 | 1.422 (6) | C45—H45B | 0.9900 |
C16—C17 | 1.358 (7) | C46—C47 | 1.479 (9) |
C16—H16 | 0.9500 | C46—H46A | 0.9900 |
C17—C18 | 1.401 (7) | C46—H46B | 0.9900 |
C17—H17 | 0.9500 | C47—C48 | 1.475 (8) |
C18—C19 | 1.368 (6) | C47—H47A | 0.9900 |
C18—H18 | 0.9500 | C47—H47B | 0.9900 |
C19—C20 | 1.403 (6) | C48—H48A | 0.9900 |
C19—H19 | 0.9500 | C48—H48B | 0.9900 |
C21—C22 | 1.365 (5) | O3—C52 | 1.393 (7) |
C21—C30 | 1.440 (5) | O3—C49 | 1.404 (7) |
C22—C23 | 1.417 (6) | C49—C50 | 1.444 (9) |
C22—H22 | 0.9500 | C49—H49A | 0.9900 |
C23—C24 | 1.366 (6) | C49—H49B | 0.9900 |
C23—H23 | 0.9500 | C50—C51 | 1.456 (9) |
C24—C25 | 1.386 (6) | C50—H50A | 0.9900 |
C24—H24 | 0.9500 | C50—H50B | 0.9900 |
C25—C30 | 1.430 (5) | C51—C52 | 1.415 (9) |
C25—C26 | 1.432 (6) | C51—H51A | 0.9900 |
C26—C27 | 1.334 (7) | C51—H51B | 0.9900 |
C26—H26 | 0.9500 | C52—H52A | 0.9900 |
C27—C28 | 1.400 (7) | C52—H52B | 0.9900 |
C27—H27 | 0.9500 | ||
N4—Si1—N1 | 100.39 (15) | C25—C30—C21 | 118.9 (4) |
N4—Si1—N3 | 112.71 (15) | C32—C31—N4 | 121.0 (3) |
N1—Si1—N3 | 116.85 (15) | C32—C31—C40 | 119.4 (4) |
N4—Si1—N2 | 115.52 (15) | N4—C31—C40 | 119.6 (4) |
N1—Si1—N2 | 112.27 (15) | C31—C32—C33 | 121.2 (4) |
N3—Si1—N2 | 99.91 (15) | C31—C32—H32 | 119.4 |
C1—N1—Si1 | 129.9 (3) | C33—C32—H32 | 119.4 |
C1—N1—H1N | 115.0 | C34—C33—C32 | 120.6 (5) |
Si1—N1—H1N | 115.0 | C34—C33—H33 | 119.7 |
C11—N2—Si1 | 129.9 (3) | C32—C33—H33 | 119.7 |
C11—N2—H2N | 115.1 | C33—C34—C35 | 120.5 (4) |
Si1—N2—H2N | 115.1 | C33—C34—H34 | 119.7 |
C21—N3—Si1 | 131.2 (3) | C35—C34—H34 | 119.7 |
C21—N3—H3N | 114.4 | C34—C35—C36 | 122.4 (5) |
Si1—N3—H3N | 114.4 | C34—C35—C40 | 120.0 (4) |
C31—N4—Si1 | 127.5 (3) | C36—C35—C40 | 117.7 (5) |
C31—N4—H4N | 116.3 | C37—C36—C35 | 122.7 (5) |
Si1—N4—H4N | 116.3 | C37—C36—H36 | 118.6 |
C2—C1—N1 | 120.4 (4) | C35—C36—H36 | 118.6 |
C2—C1—C10 | 119.4 (3) | C36—C37—C38 | 120.2 (5) |
N1—C1—C10 | 120.2 (3) | C36—C37—H37 | 119.9 |
C1—C2—C3 | 120.5 (4) | C38—C37—H37 | 119.9 |
C1—C2—H2 | 119.7 | C39—C38—C37 | 118.7 (5) |
C3—C2—H2 | 119.7 | C39—C38—H38 | 120.6 |
C4—C3—C2 | 121.0 (4) | C37—C38—H38 | 120.6 |
C4—C3—H3 | 119.5 | C38—C39—C40 | 122.5 (4) |
C2—C3—H3 | 119.5 | C38—C39—H39 | 118.7 |
C3—C4—C5 | 121.3 (4) | C40—C39—H39 | 118.7 |
C3—C4—H4 | 119.4 | C39—C40—C35 | 118.2 (4) |
C5—C4—H4 | 119.4 | C39—C40—C31 | 123.6 (4) |
C4—C5—C6 | 122.5 (4) | C35—C40—C31 | 118.3 (4) |
C4—C5—C10 | 118.4 (4) | C41—O1—C44 | 106.5 (4) |
C6—C5—C10 | 119.1 (4) | O1—C41—C42 | 106.5 (4) |
C7—C6—C5 | 121.8 (4) | O1—C41—H41A | 110.4 |
C7—C6—H6 | 119.1 | C42—C41—H41A | 110.4 |
C5—C6—H6 | 119.1 | O1—C41—H41B | 110.4 |
C6—C7—C8 | 119.1 (4) | C42—C41—H41B | 110.4 |
C6—C7—H7 | 120.5 | H41A—C41—H41B | 108.6 |
C8—C7—H7 | 120.5 | C43—C42—C41 | 102.6 (5) |
C9—C8—C7 | 121.0 (4) | C43—C42—H42A | 111.2 |
C9—C8—H8 | 119.5 | C41—C42—H42A | 111.2 |
C7—C8—H8 | 119.5 | C43—C42—H42B | 111.2 |
C8—C9—C10 | 121.9 (4) | C41—C42—H42B | 111.2 |
C8—C9—H9 | 119.1 | H42A—C42—H42B | 109.2 |
C10—C9—H9 | 119.1 | C42—C43—C44 | 106.9 (5) |
C9—C10—C5 | 117.2 (4) | C42—C43—H43A | 110.3 |
C9—C10—C1 | 123.5 (3) | C44—C43—H43A | 110.3 |
C5—C10—C1 | 119.3 (3) | C42—C43—H43B | 110.3 |
C12—C11—N2 | 121.5 (4) | C44—C43—H43B | 110.3 |
C12—C11—C20 | 119.2 (4) | H43A—C43—H43B | 108.6 |
N2—C11—C20 | 119.4 (4) | O1—C44—C43 | 106.7 (5) |
C11—C12—C13 | 121.2 (4) | O1—C44—H44A | 110.4 |
C11—C12—H12 | 119.4 | C43—C44—H44A | 110.4 |
C13—C12—H12 | 119.4 | O1—C44—H44B | 110.4 |
C14—C13—C12 | 120.4 (5) | C43—C44—H44B | 110.4 |
C14—C13—H13 | 119.8 | H44A—C44—H44B | 108.6 |
C12—C13—H13 | 119.8 | C48—O2—C45 | 108.4 (4) |
C13—C14—C15 | 121.0 (4) | O2—C45—C46 | 107.0 (5) |
C13—C14—H14 | 119.5 | O2—C45—H45A | 110.3 |
C15—C14—H14 | 119.5 | C46—C45—H45A | 110.3 |
C14—C15—C16 | 121.6 (5) | O2—C45—H45B | 110.3 |
C14—C15—C20 | 119.2 (4) | C46—C45—H45B | 110.3 |
C16—C15—C20 | 119.1 (5) | H45A—C45—H45B | 108.6 |
C17—C16—C15 | 121.2 (5) | C45—C46—C47 | 107.2 (5) |
C17—C16—H16 | 119.4 | C45—C46—H46A | 110.3 |
C15—C16—H16 | 119.4 | C47—C46—H46A | 110.3 |
C16—C17—C18 | 119.6 (5) | C45—C46—H46B | 110.3 |
C16—C17—H17 | 120.2 | C47—C46—H46B | 110.3 |
C18—C17—H17 | 120.2 | H46A—C46—H46B | 108.5 |
C19—C18—C17 | 120.7 (5) | C48—C47—C46 | 105.1 (6) |
C19—C18—H18 | 119.7 | C48—C47—H47A | 110.7 |
C17—C18—H18 | 119.7 | C46—C47—H47A | 110.7 |
C18—C19—C20 | 121.4 (4) | C48—C47—H47B | 110.7 |
C18—C19—H19 | 119.3 | C46—C47—H47B | 110.7 |
C20—C19—H19 | 119.3 | H47A—C47—H47B | 108.8 |
C19—C20—C15 | 117.9 (4) | O2—C48—C47 | 106.8 (5) |
C19—C20—C11 | 123.1 (3) | O2—C48—H48A | 110.4 |
C15—C20—C11 | 119.0 (4) | C47—C48—H48A | 110.4 |
C22—C21—N3 | 121.4 (4) | O2—C48—H48B | 110.4 |
C22—C21—C30 | 119.2 (4) | C47—C48—H48B | 110.4 |
N3—C21—C30 | 119.3 (3) | H48A—C48—H48B | 108.6 |
C21—C22—C23 | 120.5 (4) | C52—O3—C49 | 108.0 (6) |
C21—C22—H22 | 119.8 | O3—C49—C50 | 108.1 (6) |
C23—C22—H22 | 119.8 | O3—C49—H49A | 110.1 |
C24—C23—C22 | 121.2 (4) | C50—C49—H49A | 110.1 |
C24—C23—H23 | 119.4 | O3—C49—H49B | 110.1 |
C22—C23—H23 | 119.4 | C50—C49—H49B | 110.1 |
C23—C24—C25 | 120.2 (4) | H49A—C49—H49B | 108.4 |
C23—C24—H24 | 119.9 | C49—C50—C51 | 107.0 (6) |
C25—C24—H24 | 119.9 | C49—C50—H50A | 110.3 |
C24—C25—C30 | 119.9 (4) | C51—C50—H50A | 110.3 |
C24—C25—C26 | 122.4 (4) | C49—C50—H50B | 110.3 |
C30—C25—C26 | 117.8 (4) | C51—C50—H50B | 110.3 |
C27—C26—C25 | 121.9 (5) | H50A—C50—H50B | 108.6 |
C27—C26—H26 | 119.1 | C52—C51—C50 | 105.8 (7) |
C25—C26—H26 | 119.1 | C52—C51—H51A | 110.6 |
C26—C27—C28 | 120.4 (5) | C50—C51—H51A | 110.6 |
C26—C27—H27 | 119.8 | C52—C51—H51B | 110.6 |
C28—C27—H27 | 119.8 | C50—C51—H51B | 110.6 |
C29—C28—C27 | 119.8 (5) | H51A—C51—H51B | 108.7 |
C29—C28—H28 | 120.1 | O3—C52—C51 | 110.7 (6) |
C27—C28—H28 | 120.1 | O3—C52—H52A | 109.5 |
C28—C29—C30 | 122.5 (4) | C51—C52—H52A | 109.5 |
C28—C29—H29 | 118.8 | O3—C52—H52B | 109.5 |
C30—C29—H29 | 118.8 | C51—C52—H52B | 109.5 |
C29—C30—C25 | 117.6 (4) | H52A—C52—H52B | 108.1 |
C29—C30—C21 | 123.5 (4) | ||
N4—Si1—N1—C1 | 177.1 (3) | N3—C21—C22—C23 | −176.0 (3) |
N3—Si1—N1—C1 | 54.9 (3) | C30—C21—C22—C23 | 1.9 (5) |
N2—Si1—N1—C1 | −59.7 (3) | C21—C22—C23—C24 | 1.2 (6) |
N4—Si1—N2—C11 | 54.0 (4) | C22—C23—C24—C25 | −2.4 (6) |
N1—Si1—N2—C11 | −60.3 (3) | C23—C24—C25—C30 | 0.5 (6) |
N3—Si1—N2—C11 | 175.2 (3) | C23—C24—C25—C26 | −178.8 (4) |
N4—Si1—N3—C21 | −62.6 (4) | C24—C25—C26—C27 | 178.3 (4) |
N1—Si1—N3—C21 | 53.0 (4) | C30—C25—C26—C27 | −1.0 (7) |
N2—Si1—N3—C21 | 174.3 (3) | C25—C26—C27—C28 | −1.2 (8) |
N1—Si1—N4—C31 | 179.9 (3) | C26—C27—C28—C29 | 1.6 (8) |
N3—Si1—N4—C31 | −55.1 (3) | C27—C28—C29—C30 | 0.4 (7) |
N2—Si1—N4—C31 | 58.9 (3) | C28—C29—C30—C25 | −2.6 (6) |
Si1—N1—C1—C2 | −19.4 (5) | C28—C29—C30—C21 | 178.5 (4) |
Si1—N1—C1—C10 | 159.4 (3) | C24—C25—C30—C29 | −176.5 (4) |
N1—C1—C2—C3 | −178.1 (3) | C26—C25—C30—C29 | 2.8 (5) |
C10—C1—C2—C3 | 3.1 (5) | C24—C25—C30—C21 | 2.5 (5) |
C1—C2—C3—C4 | 0.5 (6) | C26—C25—C30—C21 | −178.2 (3) |
C2—C3—C4—C5 | −2.7 (6) | C22—C21—C30—C29 | 175.3 (3) |
C3—C4—C5—C6 | −177.4 (4) | N3—C21—C30—C29 | −6.8 (5) |
C3—C4—C5—C10 | 1.1 (6) | C22—C21—C30—C25 | −3.7 (5) |
C4—C5—C6—C7 | 176.7 (4) | N3—C21—C30—C25 | 174.3 (3) |
C10—C5—C6—C7 | −1.8 (6) | Si1—N4—C31—C32 | −17.8 (5) |
C5—C6—C7—C8 | 0.1 (7) | Si1—N4—C31—C40 | 163.2 (3) |
C6—C7—C8—C9 | 1.6 (7) | N4—C31—C32—C33 | −179.5 (4) |
C7—C8—C9—C10 | −1.5 (7) | C40—C31—C32—C33 | −0.5 (6) |
C8—C9—C10—C5 | −0.3 (6) | C31—C32—C33—C34 | 1.8 (7) |
C8—C9—C10—C1 | −179.4 (4) | C32—C33—C34—C35 | −1.6 (7) |
C4—C5—C10—C9 | −176.7 (3) | C33—C34—C35—C36 | −179.2 (4) |
C6—C5—C10—C9 | 1.9 (5) | C33—C34—C35—C40 | 0.0 (7) |
C4—C5—C10—C1 | 2.5 (5) | C34—C35—C36—C37 | 178.5 (5) |
C6—C5—C10—C1 | −179.0 (3) | C40—C35—C36—C37 | −0.7 (8) |
C2—C1—C10—C9 | 174.5 (3) | C35—C36—C37—C38 | 1.2 (9) |
N1—C1—C10—C9 | −4.3 (5) | C36—C37—C38—C39 | −1.4 (9) |
C2—C1—C10—C5 | −4.6 (5) | C37—C38—C39—C40 | 1.1 (7) |
N1—C1—C10—C5 | 176.7 (3) | C38—C39—C40—C35 | −0.7 (6) |
Si1—N2—C11—C12 | −10.3 (5) | C38—C39—C40—C31 | 179.1 (4) |
Si1—N2—C11—C20 | 170.7 (3) | C34—C35—C40—C39 | −178.8 (4) |
N2—C11—C12—C13 | −178.7 (4) | C36—C35—C40—C39 | 0.5 (6) |
C20—C11—C12—C13 | 0.4 (6) | C34—C35—C40—C31 | 1.3 (6) |
C11—C12—C13—C14 | 0.2 (7) | C36—C35—C40—C31 | −179.4 (4) |
C12—C13—C14—C15 | 0.1 (7) | C32—C31—C40—C39 | 179.1 (4) |
C13—C14—C15—C16 | −179.7 (4) | N4—C31—C40—C39 | −1.9 (6) |
C13—C14—C15—C20 | −1.0 (7) | C32—C31—C40—C35 | −1.1 (6) |
C14—C15—C16—C17 | 177.2 (5) | N4—C31—C40—C35 | 178.0 (3) |
C20—C15—C16—C17 | −1.5 (7) | C44—O1—C41—C42 | 32.6 (5) |
C15—C16—C17—C18 | 0.5 (8) | O1—C41—C42—C43 | −31.6 (5) |
C16—C17—C18—C19 | −0.2 (7) | C41—C42—C43—C44 | 18.8 (7) |
C17—C18—C19—C20 | 1.0 (7) | C41—O1—C44—C43 | −20.0 (6) |
C18—C19—C20—C15 | −2.0 (6) | C42—C43—C44—O1 | −0.1 (7) |
C18—C19—C20—C11 | 180.0 (4) | C48—O2—C45—C46 | −16.2 (7) |
C14—C15—C20—C19 | −176.5 (4) | O2—C45—C46—C47 | 2.1 (9) |
C16—C15—C20—C19 | 2.2 (6) | C45—C46—C47—C48 | 12.0 (10) |
C14—C15—C20—C11 | 1.6 (6) | C45—O2—C48—C47 | 23.9 (6) |
C16—C15—C20—C11 | −179.7 (4) | C46—C47—C48—O2 | −22.0 (8) |
C12—C11—C20—C19 | 176.7 (4) | C52—O3—C49—C50 | 6.0 (9) |
N2—C11—C20—C19 | −4.3 (5) | O3—C49—C50—C51 | −3.4 (10) |
C12—C11—C20—C15 | −1.3 (5) | C49—C50—C51—C52 | −0.4 (10) |
N2—C11—C20—C15 | 177.8 (3) | C49—O3—C52—C51 | −6.4 (9) |
Si1—N3—C21—C22 | −27.7 (5) | C50—C51—C52—O3 | 4.2 (10) |
Si1—N3—C21—C30 | 154.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.88 | 2.19 | 3.051 (4) | 164 |
N4—H4N···O1 | 0.88 | 2.18 | 3.028 (4) | 163 |
N2—H2N···O2 | 0.88 | 2.26 | 3.103 (5) | 160 |
N3—H3N···O2 | 0.88 | 2.17 | 3.033 (4) | 168 |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | C40H32N4Si | C40H32N4Si·3C4H8O |
Mr | 596.79 | 813.10 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/c |
Temperature (K) | 173 | 173 |
a, b, c (Å) | 10.695 (2), 22.718 (4), 13.516 (2) | 21.048 (7), 14.672 (7), 15.160 (9) |
β (°) | 109.50 (1) | 104.46 (2) |
V (Å3) | 3095.6 (9) | 4533 (4) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.10 |
Crystal size (mm) | 0.30 × 0.28 × 0.22 | 0.10 × 0.08 × 0.06 |
Data collection | ||
Diffractometer | Nonius KappaCCD area-detector diffractometer | Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1997) | Multi-scan (SORTAV; Blessing, 1997) |
Tmin, Tmax | 0.967, 0.976 | 0.990, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12258, 7035, 5131 | 17657, 9976, 3609 |
Rint | 0.031 | 0.175 |
(sin θ/λ)max (Å−1) | 0.649 | 0.650 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.122, 1.01 | 0.078, 0.230, 0.98 |
No. of reflections | 7035 | 9976 |
No. of parameters | 406 | 544 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.30 | 0.33, −0.24 |
Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).
Si1—N2 | 1.7082 (13) | N1—C1 | 1.408 (2) |
Si1—N4 | 1.7097 (14) | N2—C11 | 1.415 (2) |
Si1—N1 | 1.7125 (14) | N3—C21 | 1.404 (2) |
Si1—N3 | 1.7195 (14) | N4—C31 | 1.418 (2) |
N2—Si1—N4 | 107.00 (7) | N1—Si1—N3 | 105.52 (7) |
N2—Si1—N1 | 115.86 (7) | C1—N1—Si1 | 130.19 (11) |
N4—Si1—N1 | 107.85 (7) | C11—N2—Si1 | 127.99 (11) |
N2—Si1—N3 | 104.34 (7) | C21—N3—Si1 | 130.61 (11) |
N4—Si1—N3 | 116.63 (7) | C31—N4—Si1 | 128.33 (11) |
Si1—N1—C1—C2 | 35.2 (2) | Si1—N3—C21—C22 | −0.1 (2) |
Si1—N1—C1—C10 | −144.35 (13) | Si1—N3—C21—C30 | 179.84 (12) |
Si1—N2—C11—C12 | −22.5 (2) | Si1—N4—C31—C32 | 34.5 (2) |
Si1—N2—C11—C20 | 158.05 (12) | Si1—N4—C31—C40 | −144.82 (12) |
Si1—N4 | 1.706 (3) | N1—C1 | 1.415 (4) |
Si1—N1 | 1.709 (3) | N2—C11 | 1.399 (4) |
Si1—N3 | 1.710 (3) | N3—C21 | 1.408 (4) |
Si1—N2 | 1.715 (3) | N4—C31 | 1.416 (4) |
N4—Si1—N1 | 100.39 (15) | N3—Si1—N2 | 99.91 (15) |
N4—Si1—N3 | 112.71 (15) | C1—N1—Si1 | 129.9 (3) |
N1—Si1—N3 | 116.85 (15) | C11—N2—Si1 | 129.9 (3) |
N4—Si1—N2 | 115.52 (15) | C21—N3—Si1 | 131.2 (3) |
N1—Si1—N2 | 112.27 (15) | C31—N4—Si1 | 127.5 (3) |
Si1—N1—C1—C2 | −19.4 (5) | Si1—N3—C21—C22 | −27.7 (5) |
Si1—N1—C1—C10 | 159.4 (3) | Si1—N3—C21—C30 | 154.5 (3) |
Si1—N2—C11—C12 | −10.3 (5) | Si1—N4—C31—C32 | −17.8 (5) |
Si1—N2—C11—C20 | 170.7 (3) | Si1—N4—C31—C40 | 163.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.88 | 2.19 | 3.051 (4) | 164.1 |
N4—H4N···O1 | 0.88 | 2.18 | 3.028 (4) | 163.0 |
N2—H2N···O2 | 0.88 | 2.26 | 3.103 (5) | 159.5 |
N3—H3N···O2 | 0.88 | 2.17 | 3.033 (4) | 168.3 |
The lithiated homoleptic polyimide complexes of main group elements are of great interest due to their versatility in forming a variety of clusters and cages (Brask & Chivers, 2001; Aspinall et al., 2002). The aggregation depends to a large extent on the bulk of the nitrogen substituents. Recently, we reported the crystal structure of a novel tetrakis(imide) tetraanion, [Si(Nnaph)4][{Li·(THF)2}2{Li·OEt2}2]·Et2O (Copsey et al., 2006a) (naph is naphthylimide ? and THF is tetrahydrofuran). In this paper, we report the structures of [Si(NHnaph)4], (I), and its tetrahydrofuran trisolvate, [Si(NHnaph)4]·3THF, (II). Compound (I) was also prepared earlier by interacting tert-butylammonium chloride with [Si(Nnaph)4][Li·OEt2]4 (Brask et al., 2000).
The structure of (I) (Fig. 1) contains independent molecules wherein the naphthalene rings are individually planar, with maximum deviations of the atoms from the mean-planes of 0.0365 (13), 0.0232 (15), 0.0381 (13) and 0.0297 (15) Å for atoms C1, C18, C29 and C33 from the least-squares planes of the naphthalene rings C1–C10, C11–C20, C21–C30 and C31–C40, respectively. The rings C1–C10 and C31–C40 are inclined at 16.11 (5)° with respect to each other, while the other two rings lie approximately at right angles to these planes; the angle between the rings C1–C10 and C11–C21 is 83.27 (3)°, while the angle between the rings C21–C30 and C31–C40 is 74.13 (4)°. The N atoms deviate significantly from the mean planes of the rings, with atoms N1, N2, N3 and N4 lying 0.083 (2), 0.018 (2), 0.058 (2) and 0.042 (2) Å out of the respective naphthalene rings. Furthermore, the angles around Si1 deviate significantly from the tetrahedral value and lie in a wide range, between 104.34 (7) and 116.63 (7)°; the Si—N—C angles lie in a narrow range of 127.99 (11)–130.61 (11)°.
The structure of (II) (Fig. 2), on the other hand, contains independent molecules of (I) hydrogen bonded to two THF molecules (Table 3) and a third solvent THF molecule, which is not involved in any close interactions. The naphthalene rings in (II) are also individually planar, with maximum deviations of the atoms from the mean-planes of 0.051 (3), 0.024 (4), 0.048 (3) and 0.020 (4) Å for atoms C3, C13, C21 and C33 from the least-squares planes of the naphthalene rings C1–C10, C11–C20, C21–C30 and C31–C40, respectively. The orientation of naphthalene rings is influenced by the hydrogen-bonded THF molecules. Thus, the mean-planes of the rings C1–C10 and C31–C40 in (II) form an angle of 40.90 (11)°, compared with 16.11 (5)° in (I). The rings C1–C10 and C11–C20 lie approximately at right angles [85.52 (8)°], while the angle between the rings C21–C30 and C31–C40 is 81.29 (9)°.
The N atoms in (II) deviate from the mean-planes of the rings even more than the corresponding N atoms in (I), with atoms N1, N2, N3 and N4 lying 0.120 (4), 0.073 (5), 0.173 (4) and 0.048 (5) Å out of the mean planes of the respective naphthalene rings. Furthermore, the tetrahedral angles around Si1 in (II) also lie in a wide range, between 99.91 (15) and 116.85 (15)°, while the Si—N—C angles lie in a narrow range of 127.5 (3)–131.2 (3)°. Similar bond angles around Si and N atoms have been observed in closely related structures, e.g. tetrakis(phenylamino)silane (Clade & Jansen, 2005), tetrakis(2-fluorophenylamino)silane (Mokros & Jansen, 1996) and tetrakis(pentafluorophenylamino)silane (Jansen et al., 1992).
The conformational differences between the silane molecules in (I) and (II) are evident from a comparison of the Si—N—C—C torsion angles listed in Tables 1 and 2, and of Figs. 1 and 2. The THF molecules O1/C41–C44 and O2/C45–C48 in (II) adopt C41- and C48-envelope conformations, with atoms C41 and C48 0.469 (7) and 0.335 (9) Å, respectively, out of the planes of the remaining ring atoms. The third molecule of THF, O3/C49–C52, is apparently planar, with a maximum deviation of 0.036 (3) Å for atom O3, but this component may be subject to some disorder.