Tetra­kis(2-meth­oxy-5-pyrid­yl)silane

The title compound, C₂₄H₂₄N₄O₄Si, crystallizes from propionic acid-hexane to produce a close-packed structure with no included guests. In contrast, crystallization of the closely related tetra­kis(1,2-dihydro-2-oxo-5-pyrid­yl)silane under similar conditions is directed by hydrogen bonding of the pyridinone groups to yield an open diamondoid network, which is filled by a combination of inter­penetration and inclusion of guests.

Key indicators

• Single-crystal X-ray study
• T = 225 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.057
• wR factor = 0.173
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         N1
                    C14    N1     C12    C11
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C1
                    C16    C1     C12    N13
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C1
                    SI     C1     C12    N13
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         N1
                    C12    N1     C14    O14
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         N1
                    C12    N1     C14    C15
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         O1
                    C17    O1     C14    N13
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         O1
                    C17    O1     C14    C15
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C1
                    N13    C1     C15    C16
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C1
                    O14    C1     C15    C16
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C1
                    C14    C1     C16    C11
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C1
                    C12    C1     C16    C15
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C1
                    SI     C1     C16    C15
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         N2
                    C24    N2     C22    C21
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C2
                    C26    C2     C22    N23
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C2
                    SI     C2     C22    N23
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         N2
                    C22    N2     C24    O24
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         N2
                    C22    N2     C24    C25
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         O2
                    C27    O2     C24    N23
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         O2
                    C27    O2     C24    C25
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C2
                    N23    C2     C25    C26
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C2
                    O24    C2     C25    C26
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C2
                    C24    C2     C26    C21
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C2
                    C22    C2     C26    C25
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C2
                    SI     C2     C26    C25
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         N3
                    C34    N3     C32    C31
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C3
                    C36    C3     C32    N33
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C3
                    SI     C3     C32    N33
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         N3
                    C32    N3     C34    O34
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         N3
                    C32    N3     C34    C35
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         O3
                    C37    O3     C34    N33
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         O3
                    C37    O3     C34    C35
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C3
                    N33    C3     C35    C36
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C3
                    O34    C3     C35    C36
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C3
                    C34    C3     C36    C31
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C3
                    C32    C3     C36    C35
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C3
                    SI     C3     C36    C35
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         N4
                    C44    N4     C42    C41
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C4
                    C46    C4     C42    N43
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C4
                    SI     C4     C42    N43
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         N4
                    C42    N4     C44    O44
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         N4
                    C42    N4     C44    C45
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         O4
                    C47    O4     C44    N43
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         O4
                    C47    O4     C44    C45
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C4
                    N43    C4     C45    C46
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C4
                    O44    C4     C45    C46
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C4
                    C44    C4     C46    C41
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C4
                    C42    C4     C46    C45
PLAT713_ALERT_1_C TORSION Unknown or Inconsistent Label ..........         C4
                    SI     C4     C46    C45

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  48 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

  48 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: modified versions of NRC-2/NRC2A (Ahmed et al., 1973); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Tetrakis(2-methoxy-5-pyridyl)silane

Crystal data

C24H24N4O4Si	Z = 2
Mr = 460.56	F(000) = 484
Triclinic, P1	Dx = 1.342 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 9.661 (3) Å	Cell parameters from 25 reflections
b = 10.364 (4) Å	θ = 15.0–30.0°
c = 12.230 (6) Å	µ = 1.24 mm^−1
α = 107.74 (4)°	T = 225 K
β = 94.68 (3)°	Block, colorless
γ = 99.22 (3)°	0.52 × 0.48 × 0.18 mm
V = 1140.1 (9) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	3964 reflections with I > 2σ(I)
Radiation source: X-ray sealed tube	Rint = 0.078
Graphite monochromator	θmax = 69.8°, θmin = 3.8°
ω/2θ scans	h = −11→11
Absorption correction: analytical (ABSORP in NRCVAX; Gabe et al., 1989)	k = −12→12
Tmin = 0.570, Tmax = 0.810	l = −14→14
8614 measured reflections	6 standard reflections every 60 min
4319 independent reflections	intensity decay: 0.1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.173	w = 1/[σ^2(Fo^2) + (0.1135P)^2 + 0.4013P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
4319 reflections	Δρmax = 0.43 e Å^−3
302 parameters	Δρmin = −0.53 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0133 (15)

Special details

Experimental. X-ray crystallographic data for I were collected from a single-crystal sample, which was mounted on a glass fiber. Data were collected using an Enraf–Nonius CAD4 diffractometer equipped with FR590 generator, a Kappa goniometer, a standard scintillation counter and a locally modified low temperature device. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of 25 strong reflections. The intensity of some selected strong reflections was monitored during the course of the data collection. Data were corrected for absorption, Lorentz and polarization effects

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Si	0.28028 (5)	0.24267 (5)	0.32296 (5)	0.0327 (2)
O14	0.53201 (18)	0.13402 (16)	0.73881 (14)	0.0463 (4)
O24	0.05137 (19)	0.76165 (16)	0.45700 (14)	0.0488 (4)
O34	−0.18124 (16)	−0.21736 (16)	0.03363 (13)	0.0464 (4)
O44	0.79059 (17)	0.35816 (18)	0.10007 (16)	0.0517 (4)
N13	0.5264 (2)	0.26889 (18)	0.62133 (16)	0.0410 (4)
N23	0.0789 (2)	0.56330 (19)	0.31729 (16)	0.0413 (4)
N33	−0.10641 (19)	−0.01673 (19)	0.18841 (16)	0.0409 (4)
N43	0.5946 (2)	0.42981 (18)	0.17707 (16)	0.0393 (4)
C11	0.3500 (2)	0.1973 (2)	0.45052 (18)	0.0343 (4)
C12	0.4638 (2)	0.2871 (2)	0.52634 (19)	0.0402 (5)
H12	0.5006	0.3677	0.5100	0.048*
C14	0.4734 (2)	0.1558 (2)	0.64314 (18)	0.0368 (5)
C15	0.3609 (2)	0.0552 (2)	0.5738 (2)	0.0427 (5)
H15	0.3278	−0.0251	0.5922	0.051*
C16	0.2997 (2)	0.0778 (2)	0.47714 (19)	0.0400 (5)
H16	0.2233	0.0120	0.4285	0.048*
C17	0.6353 (3)	0.2466 (3)	0.8163 (2)	0.0569 (7)
H17A	0.5950	0.3293	0.8376	0.085*
H17B	0.7177	0.2624	0.7783	0.085*
H17C	0.6630	0.2245	0.8855	0.085*
C21	0.2040 (2)	0.4026 (2)	0.37185 (17)	0.0346 (4)
C22	0.1313 (3)	0.4464 (2)	0.29208 (19)	0.0420 (5)
H22	0.1174	0.3901	0.2141	0.050*
C24	0.0992 (2)	0.6409 (2)	0.42661 (18)	0.0374 (5)
C25	0.1683 (2)	0.6080 (2)	0.51605 (19)	0.0422 (5)
H25	0.1795	0.6664	0.5933	0.051*
C26	0.2193 (2)	0.4882 (2)	0.48796 (18)	0.0377 (5)
H26	0.2651	0.4626	0.5467	0.045*
C27	−0.0282 (3)	0.7912 (3)	0.3666 (2)	0.0525 (6)
H27A	−0.0518	0.8817	0.3970	0.079*
H27B	−0.1145	0.7220	0.3374	0.079*
H27C	0.0279	0.7898	0.3041	0.079*
C31	0.1398 (2)	0.0977 (2)	0.22623 (17)	0.0348 (4)
C32	0.0024 (2)	0.0850 (2)	0.24998 (18)	0.0405 (5)
H32	−0.0172	0.1530	0.3145	0.049*
C34	−0.0767 (2)	−0.1118 (2)	0.09871 (17)	0.0368 (5)
C35	0.0568 (2)	−0.1119 (2)	0.06465 (19)	0.0414 (5)
H35	0.0730	−0.1822	0.0001	0.050*
C36	0.1645 (2)	−0.0056 (2)	0.12877 (19)	0.0398 (5)
H36	0.2558	−0.0018	0.1072	0.048*
C37	−0.3191 (3)	−0.2177 (3)	0.0694 (2)	0.0569 (7)
H37A	−0.3143	−0.2198	0.1484	0.085*
H37B	−0.3849	−0.2986	0.0185	0.085*
H37C	−0.3512	−0.1350	0.0656	0.085*
C41	0.4374 (2)	0.2765 (2)	0.24831 (17)	0.0339 (4)
C42	0.4786 (2)	0.3985 (2)	0.22550 (18)	0.0366 (5)
H42	0.4213	0.4651	0.2453	0.044*
C44	0.6736 (2)	0.3348 (2)	0.15048 (18)	0.0375 (5)
C45	0.6449 (2)	0.2081 (2)	0.1696 (2)	0.0422 (5)
H45	0.7046	0.1438	0.1489	0.051*
C46	0.5270 (2)	0.1803 (2)	0.21969 (19)	0.0396 (5)
H46	0.5057	0.0963	0.2351	0.047*
C47	0.8219 (3)	0.4862 (3)	0.0766 (3)	0.0610 (7)
H47A	0.8175	0.4680	−0.0063	0.092*
H47B	0.9162	0.5351	0.1145	0.092*
H47C	0.7533	0.5423	0.1059	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si	0.0312 (3)	0.0295 (3)	0.0318 (3)	−0.0033 (2)	0.0037 (2)	0.0067 (2)
O14	0.0557 (10)	0.0404 (8)	0.0414 (8)	0.0029 (7)	0.0009 (7)	0.0162 (7)
O24	0.0571 (10)	0.0375 (9)	0.0465 (9)	0.0100 (7)	0.0096 (7)	0.0048 (7)
O34	0.0394 (8)	0.0413 (9)	0.0419 (8)	−0.0101 (7)	0.0022 (7)	−0.0004 (7)
O44	0.0424 (9)	0.0508 (10)	0.0590 (10)	0.0000 (7)	0.0216 (8)	0.0145 (8)
N13	0.0429 (10)	0.0332 (9)	0.0418 (10)	−0.0051 (7)	−0.0003 (8)	0.0127 (8)
N23	0.0429 (10)	0.0380 (10)	0.0377 (9)	0.0049 (8)	0.0044 (7)	0.0063 (8)
N33	0.0334 (9)	0.0393 (10)	0.0389 (9)	−0.0033 (7)	0.0062 (7)	0.0018 (8)
N43	0.0409 (10)	0.0328 (9)	0.0400 (9)	−0.0017 (7)	0.0108 (7)	0.0090 (7)
C11	0.0330 (10)	0.0318 (10)	0.0342 (10)	−0.0017 (8)	0.0066 (8)	0.0086 (8)
C12	0.0398 (11)	0.0338 (10)	0.0430 (11)	−0.0085 (8)	−0.0019 (9)	0.0164 (9)
C14	0.0424 (11)	0.0316 (10)	0.0362 (10)	0.0056 (8)	0.0102 (9)	0.0104 (8)
C15	0.0475 (12)	0.0324 (10)	0.0469 (12)	−0.0037 (9)	0.0076 (10)	0.0161 (9)
C16	0.0391 (11)	0.0315 (10)	0.0417 (11)	−0.0070 (8)	0.0036 (9)	0.0080 (8)
C17	0.0597 (16)	0.0553 (15)	0.0486 (14)	−0.0023 (12)	−0.0110 (12)	0.0181 (12)
C21	0.0304 (10)	0.0323 (10)	0.0350 (10)	−0.0029 (7)	0.0051 (8)	0.0062 (8)
C22	0.0493 (12)	0.0354 (11)	0.0330 (10)	0.0028 (9)	0.0035 (9)	0.0022 (8)
C24	0.0346 (10)	0.0313 (10)	0.0401 (11)	−0.0004 (8)	0.0083 (8)	0.0055 (8)
C25	0.0435 (12)	0.0396 (11)	0.0322 (10)	−0.0011 (9)	0.0055 (9)	0.0001 (9)
C26	0.0338 (10)	0.0390 (11)	0.0338 (10)	−0.0024 (8)	0.0033 (8)	0.0077 (8)
C27	0.0553 (15)	0.0437 (13)	0.0582 (15)	0.0133 (11)	0.0101 (12)	0.0135 (11)
C31	0.0371 (10)	0.0303 (10)	0.0322 (10)	−0.0016 (8)	0.0054 (8)	0.0070 (8)
C32	0.0379 (11)	0.0369 (11)	0.0352 (10)	−0.0010 (8)	0.0054 (8)	−0.0009 (8)
C34	0.0393 (11)	0.0316 (10)	0.0315 (10)	−0.0038 (8)	0.0016 (8)	0.0052 (8)
C35	0.0408 (12)	0.0357 (11)	0.0381 (11)	0.0018 (9)	0.0077 (9)	0.0002 (9)
C36	0.0354 (11)	0.0386 (11)	0.0395 (11)	0.0011 (9)	0.0093 (9)	0.0062 (9)
C37	0.0374 (12)	0.0565 (15)	0.0576 (15)	−0.0106 (11)	0.0013 (11)	0.0019 (12)
C41	0.0340 (10)	0.0312 (10)	0.0315 (9)	−0.0010 (8)	0.0023 (8)	0.0071 (8)
C42	0.0356 (10)	0.0316 (10)	0.0385 (10)	0.0015 (8)	0.0077 (8)	0.0074 (8)
C44	0.0326 (10)	0.0382 (11)	0.0333 (10)	−0.0028 (8)	0.0063 (8)	0.0040 (8)
C45	0.0381 (11)	0.0380 (11)	0.0469 (12)	0.0063 (9)	0.0077 (9)	0.0086 (9)
C46	0.0401 (11)	0.0318 (10)	0.0442 (11)	0.0004 (8)	0.0058 (9)	0.0118 (9)
C47	0.0563 (16)	0.0574 (16)	0.0664 (17)	−0.0080 (12)	0.0243 (13)	0.0214 (13)

Geometric parameters (Å, º)

Si—C11	1.867 (2)	C21—C22	1.383 (3)
Si—C31	1.871 (2)	C21—C26	1.408 (3)
Si—C21	1.872 (2)	C22—H22	0.94
Si—C41	1.874 (2)	C24—C25	1.392 (3)
O14—C14	1.354 (3)	C25—C26	1.367 (3)
O14—C17	1.433 (3)	C25—H25	0.94
O24—C24	1.360 (3)	C26—H26	0.94
O24—C27	1.432 (3)	C27—H27A	0.97
O34—C34	1.354 (3)	C27—H27B	0.97
O34—C37	1.435 (3)	C27—H27C	0.97
O44—C44	1.354 (3)	C31—C32	1.377 (3)
O44—C47	1.433 (3)	C31—C36	1.405 (3)
N13—C14	1.315 (3)	C32—H32	0.94
N13—C12	1.344 (3)	C34—C35	1.388 (3)
N23—C24	1.313 (3)	C35—C36	1.373 (3)
N23—C22	1.347 (3)	C35—H35	0.94
N33—C34	1.319 (3)	C36—H36	0.94
N33—C32	1.348 (3)	C37—H37A	0.97
N43—C44	1.320 (3)	C37—H37B	0.97
N43—C42	1.349 (3)	C37—H37C	0.97
C11—C12	1.384 (3)	C41—C42	1.381 (3)
C11—C16	1.398 (3)	C41—C46	1.407 (3)
C12—H12	0.94	C42—H42	0.94
C14—C15	1.391 (3)	C44—C45	1.392 (3)
C15—C16	1.379 (3)	C45—C46	1.368 (3)
C15—H15	0.94	C45—H45	0.94
C16—H16	0.94	C46—H46	0.94
C17—H17A	0.97	C47—H47A	0.97
C17—H17B	0.97	C47—H47B	0.97
C17—H17C	0.97	C47—H47C	0.97
C11—SI—C31	110.28 (10)	C21—C26—H26	119.7
C11—SI—C21	110.38 (10)	O24—C27—H27A	109.5
C31—SI—C21	109.15 (10)	O24—C27—H27B	109.5
C11—SI—C41	105.43 (10)	H27A—C27—H27B	109.5
C31—SI—C41	111.96 (10)	O24—C27—H27C	109.5
C21—SI—C41	109.59 (10)	H27A—C27—H27C	109.5
C14—O14—C17	116.00 (18)	H27B—C27—H27C	109.5
C24—O24—C27	116.65 (18)	C32—C31—C36	115.50 (19)
C34—O34—C37	116.28 (18)	C32—C31—SI	120.23 (15)
C44—O44—C47	117.65 (19)	C36—C31—SI	124.25 (16)
C14—N13—C12	116.36 (18)	N33—C32—C31	125.43 (19)
C24—N23—C22	116.7 (2)	N33—C32—H32	117.3
C34—N33—C32	116.43 (19)	C31—C32—H32	117.3
C44—N43—C42	116.22 (19)	N33—C34—O34	119.4 (2)
C12—C11—C16	115.35 (19)	N33—C34—C35	124.32 (19)
C12—C11—SI	118.50 (15)	O34—C34—C35	116.31 (19)
C16—C11—SI	126.13 (16)	C36—C35—C34	117.5 (2)
N13—C12—C11	125.67 (19)	C36—C35—H35	121.3
N13—C12—H12	117.2	C34—C35—H35	121.3
C11—C12—H12	117.2	C35—C36—C31	120.8 (2)
N13—C14—O14	118.39 (19)	C35—C36—H36	119.6
N13—C14—C15	124.4 (2)	C31—C36—H36	119.6
O14—C14—C15	117.20 (19)	O34—C37—H37A	109.5
C16—C15—C14	117.36 (19)	O34—C37—H37B	109.5
C16—C15—H15	121.3	H37A—C37—H37B	109.5
C14—C15—H15	121.3	O34—C37—H37C	109.5
C15—C16—C11	120.8 (2)	H37A—C37—H37C	109.5
C15—C16—H16	119.6	H37B—C37—H37C	109.5
C11—C16—H16	119.6	C42—C41—C46	115.94 (19)
O14—C17—H17A	109.5	C42—C41—SI	123.22 (16)
O14—C17—H17B	109.5	C46—C41—SI	120.69 (16)
H17A—C17—H17B	109.5	N43—C42—C41	125.2 (2)
O14—C17—H17C	109.5	N43—C42—H42	117.4
H17A—C17—H17C	109.5	C41—C42—H42	117.4
H17B—C17—H17C	109.5	N43—C44—O44	119.5 (2)
C22—C21—C26	115.5 (2)	N43—C44—C45	124.48 (19)
C22—C21—SI	120.47 (16)	O44—C44—C45	116.0 (2)
C26—C21—SI	124.04 (17)	C46—C45—C44	117.7 (2)
N23—C22—C21	125.2 (2)	C46—C45—H45	121.2
N23—C22—H22	117.4	C44—C45—H45	121.2
C21—C22—H22	117.4	C45—C46—C41	120.5 (2)
N23—C24—O24	119.4 (2)	C45—C46—H46	119.8
N23—C24—C25	124.1 (2)	C41—C46—H46	119.8
O24—C24—C25	116.52 (19)	O44—C47—H47A	109.5
C26—C25—C24	117.9 (2)	O44—C47—H47B	109.5
C26—C25—H25	121.1	H47A—C47—H47B	109.5
C24—C25—H25	121.1	O44—C47—H47C	109.5
C25—C26—C21	120.6 (2)	H47A—C47—H47C	109.5
C25—C26—H26	119.7	H47B—C47—H47C	109.5
C31—SI—C11—C12	174.20 (17)	C11—SI—C31—C32	83.4 (2)
C21—SI—C11—C12	−65.1 (2)	C21—SI—C31—C32	−38.1 (2)
C41—SI—C11—C12	53.16 (19)	C41—SI—C31—C32	−159.57 (17)
C31—SI—C11—C16	−4.5 (2)	C11—SI—C31—C36	−95.0 (2)
C21—SI—C11—C16	116.21 (19)	C21—SI—C31—C36	143.55 (19)
C41—SI—C11—C16	−125.52 (19)	C41—SI—C31—C36	22.0 (2)
C14—N1—C12—C11	−0.2 (3)	C34—N3—C32—C31	0.5 (4)
C16—C1—C12—N13	−0.8 (3)	C36—C3—C32—N33	0.3 (3)
SI—C1—C12—N13	−179.61 (18)	SI—C3—C32—N33	−178.21 (18)
C12—N1—C14—O14	−179.18 (19)	C32—N3—C34—O34	179.60 (19)
C12—N1—C14—C15	1.3 (3)	C32—N3—C34—C35	−0.6 (3)
C17—O1—C14—N13	8.1 (3)	C37—O3—C34—N33	−0.6 (3)
C17—O1—C14—C15	−172.3 (2)	C37—O3—C34—C35	179.5 (2)
N13—C1—C15—C16	−1.3 (3)	N33—C3—C35—C36	−0.2 (4)
O14—C1—C15—C16	179.2 (2)	O34—C3—C35—C36	179.6 (2)
C14—C1—C16—C11	0.2 (3)	C34—C3—C36—C31	1.1 (3)
C12—C1—C16—C15	0.8 (3)	C32—C3—C36—C35	−1.1 (3)
SI—C1—C16—C15	179.48 (17)	SI—C3—C36—C35	177.33 (17)
C11—SI—C21—C22	−172.37 (17)	C11—SI—C41—C42	−124.20 (18)
C31—SI—C21—C22	−51.00 (19)	C31—SI—C41—C42	115.86 (18)
C41—SI—C21—C22	71.94 (19)	C21—SI—C41—C42	−5.4 (2)
C11—SI—C21—C26	9.9 (2)	C11—SI—C41—C46	51.09 (19)
C31—SI—C21—C26	131.28 (17)	C31—SI—C41—C46	−68.85 (19)
C41—SI—C21—C26	−105.78 (18)	C21—SI—C41—C46	169.89 (16)
C24—N2—C22—C21	0.1 (3)	C44—N4—C42—C41	−0.2 (3)
C26—C2—C22—N23	1.5 (3)	C46—C4—C42—N43	1.2 (3)
SI—C2—C22—N23	−176.37 (18)	SI—C4—C42—N43	176.66 (16)
C22—N2—C24—O24	178.60 (19)	C42—N4—C44—O44	179.05 (19)
C22—N2—C24—C25	−1.3 (3)	C42—N4—C44—C45	−0.3 (3)
C27—O2—C24—N23	4.3 (3)	C47—O4—C44—N43	−0.7 (3)
C27—O2—C24—C25	−175.8 (2)	C47—O4—C44—C45	178.7 (2)
N23—C2—C25—C26	0.7 (3)	N43—C4—C45—C46	−0.2 (3)
O24—C2—C25—C26	−179.13 (19)	O44—C4—C45—C46	−179.54 (19)
C24—C2—C26—C21	1.0 (3)	C44—C4—C46—C41	1.2 (3)
C22—C2—C26—C25	−2.0 (3)	C42—C4—C46—C45	−1.6 (3)
SI—C2—C26—C25	175.80 (16)	SI—C4—C46—C45	−177.23 (17)