Tetra­kis(1-naphthyl­amino)silane and its tetra­hydro­furan tris­olvate

In both title structures, C₄₀H₃₂N₄Si and C₄₀H₃₂N₄Si·3C₄H₈O, the angles around the Si atom deviate significantly from the tetra­hedral value [104.34 (7)-116.63 (7)° in the nonsolvate and 99.91 (15)-116.85 (15)° in the solvate]. The amino H atoms in the solvated structure are involved in hydrogen bonding with two of the tetra­hydro­furan solvent mol­ecules.

S1. Comment

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.

S2. Experimental

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).

S3. Refinement

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 U_iso(H) = 1.2U_eq(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.

Computing details

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).

Figures

	Fig. 1. A drawing of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A drawing of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 20% probability level and H atoms are shown as small spheres of arbitrary radii. Dashed lines indicate hydrogen bonds.

(I) Tetrakis(1-naphthylamino)silane

Crystal data

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) Å^3	0.30 × 0.28 × 0.22 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.057P)^2 + 0.89P] where P = (Fo^2 + 2Fc^2)/3
7035 reflections	(Δ/σ)max < 0.001
406 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

(II) Tetrakis(1-naphthylamino)silane tetrahydrofuran trisolvate

Crystal data

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) Å^3	0.10 × 0.08 × 0.06 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.230	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.092P)^2] where P = (Fo^2 + 2Fc^2)/3
9976 reflections	(Δ/σ)max = 0.005
544 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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