Dynamic disorder in a penta­coordin­ate silicon complex with 2,2′-diazenediyldiphenol

The crystal structure of (2,2′-diazenediyldiphenolato-κ³O,N,O′)dimethyl­silicon, C₁₄H₁₄N₂O₂Si, determined at four temperatures, reveals a dynamic disorder as a result of a flipping of the orientation of the C—N=N—C unit. The population of the two conformers in the single crystal depends on the temperature and cooling rate. It is possible to minimize the disorder by cooling the crystal slowly.

S1. Comment

The chemistry of hypercoordinate silicon complexes is currently one of the main research areas in silicon chemistry (Chuit et al., 1993; Corriu & Young, 1989; Holmes, 1996; Kost & Kalikhman, 1998, 2004; Pestunovich et al., 1998; Tacke et al., 1999). During our work on penta- and hexacoordinate silicon complexes with tridentate O,N,O-ligands (Böhme et al., 2006; Böhme & Günther, 2007; Böhme & Foehn, 2007), we used 2,2'-dihydroxyazobenzene, (I), as a potential ligand molecule. The reaction of (I) with dichlorodimethylsilane in the presence of triethylamine in tetrahydrofuran (THF) yields, after workup, a red crystalline product. The X-ray crystal structure analysis of a suitable crystal at room temperature verified the formation of the title pentacoordinate silicon complex, (II) (Fig. 1).

In (II), the Si atom is bound to the C atoms of the methyl groups (atoms C13 and C14) and to the two O atoms and one of the N atoms of the 2,2'-dioxoazobenzene moiety. There is disorder in the structure as a result of a flipping of the orientation of the C—N═N—C unit. Essentially, the 2,2'-dioxoazobenzene moiety is superimposed on a mirror image of itself in the plane bisecting the C1···C7 line (Fig. 1). Thus, all atoms of the 2,2'-dioxoazobenzene moiety are expected to be disordered, but only the N and O atoms could be modelled successfully as disordered (see Experimental section). The occupancy of the minor conformation is 17.4 (3)%. An attempt was made to diminish the disorder by cooling the crystal to 153 K over a period of 1 h. After a fresh data collection, the proportion of disordered molecules in the crystal was estimated to be 4.1 (2)%. This result points to the presence of dynamic disorder. The crystal – having been warmed to room temperature – was then flash-cooled to 93 K. The subsequent X-ray structure analysis shows in this case that the disorder is nearly identical to that in the sample measured at room temperature [13.4 (3)%]. The possibility of observing unstable conformers in flash-cooled crystals has been demonstrated previously (Harada & Ogawa, 2004). The crystal was warmed again to room temperature and then cooled slowly within 2 h to 93 K. The fourth determination of the crystal structure shows that the disorder is reduced to a minimum proportion of 4.1 (2)%. All four crystal structure determinations were performed with the same crystal, and the crystal was warmed to room temperature between every measurement.

The best results were achieved with the structure determination at 153 K (Fig. 2) and some of the main geometric features of the structure at this temperature are as follows. The Si—O distances [Si1—O1A = 1.7136 (12) Å and Si1—O2A = 1.7014 (12) Å] are short but comparable to those of similar compounds (Böhme & Günther, 2007;). The Si—C distances are in the usual range [Si1—C13 = 1.8594 (15) Å and Si1—C14 = 1.8684 (15) Å]. The Si—N distances are longer than expected [Si1—N1A = 2.1666 (13) Å and Si1—N2B 2.172 (5) Å], which is easily explained by the coordinative character of this bond. One might think that 95.9 (5)% site occupation is not really distinguishable from 100%. However, if the structure of (II) at 153 K is refined without treatment of the disorder, the R value rises from 0.0384 to 0.0406 and the residual density map (Fig. 3) shows sharp peaks of residual electron density for the disordered nitrogen atoms and smaller peaks for the rest of the 2,2'-dioxoazobenzene unit.

Dynamic disorder has often been observed in azobenzene and stilbene derivatives (Bernstein, 1975; Borbulevych & Antipin, 2001; Harada et al., 1997; Harada & Ogawa, 2004). Surprisingly, it was now detected in the silicon complex (II). The mechanism of rearrangement in the solid state has been explained with a `pedal motion' (Harada et al., 1997). The energy necessary to perform such a "pedal motion", i.e. the rotation of the –N═N– unit, for one single molecule of (II) in the gas phase has been calculated at the B3LYP/6–31G(d,p) level with a free enthalpy of 55.4 kJ mol^-1. The geometry of the calculated transition state is shown in Fig. 4. Another mechanism of rearrangement would be the inversion of the SiMe₂ group. This inversion has an activation energy of only 8.0 kJ mol^-1 in free enthalpy [B3LYP/6–31G(d,p)], which is easily possible in solution but is unlikely to take place in the crystalline state.

To interpret the results of the crystal structure determinations one can say the following: if there is a crystalline sample that raises suspicion of dynamic disorder, it is useful to cool the sample slowly. Flash-cooling or quick-freezing, as is often practiced in routine crystallographic work, is not the best approach in every case. Of course we are aware that there is not always enough time to make a number of different structure determinations from a given crystal, but in some cases it might help to keep these conclusions in mind during daily crystallographic practice.

Related literature

For related literature, see: Böhme & Foehn (2007); Böhme & Günther (2007); Böhme et al. (2006); Bernstein (1975); Borbulevych & Antipin (2001); Chuit et al. (1993); Corriu & Young (1989); Harada & Ogawa (2004); Harada et al. (1997); Holmes (1996); Kost & Kalikhman (1998, 2004); Pestunovich et al. (1998); Tacke et al. (1999).

S2. Experimental

The preparation of (II) was performed in Schlenk tubes under argon with dry and air-free solvents. Me₂SiCl₂ (0.84 g, 0.0065 mol) and triethyl amine (1.46 g, 0.0144 mol) were dissolved in THF (80 ml) and cooled to 273 K. 2,2'-Dihydroxyazobenzene (1.4 g, 0.0065 mol) was dissolved in THF (60 ml) and added dropwise to the stirred mixture of Me₂SiCl₂ and triethyl amine. A precipitate was formed immediately and the mixture became red. After removal of the cooling bath, the mixture was stirred at room temperature for 70 h. The suspension was filtered into a Schlenk tube and the remaining solid, which is NEt₃HCl, was washed with small amounts of THF. The solvent was completely removed in vacuo and the red residue was recrystallized with 1,2-dimethoxyethane (yield 1.4 g, 79.7%; m.p. 388 K). Crystals suitable for X-ray structure analysis were obtained by recrystallization from diethyl ether. Analysis calculated for C₁₄H₁₄N₂O₂Si: C 62.20, H 5.22, N 10.36%; found: C 62.08, H 5.18, N 10.53%. ²⁹Si NMR (CDCl₃): δ -50.2; ¹H NMR (CDCl₃): δ 0.15 (s, Me, 6H), 7.0–7.5 (m, Ph, 8H); ¹³C NMR (CDCl₃): δ 1.7 (Me), 120.5, 121.5, 123.3, 134.5, 138.2, 152.6 (6 signals for Ph) p.p.m.].

S3. Refinement

Evidence was found for disorder of the 2,2'-dioxoazobenzene unit, as discussed in the Comment section. It would be desirable to define two positions for all atoms of the 2,2'-dioxoazobenzene unit, since the benzene rings must have disordered orientations as well (cf. Fig. 3 and geometrical considerations). However, such a treatment of the structure model makes the refinement unstable. As a compromise, only the nitrogen and oxygen atoms were treated with a split atom model. This model reflects the major aspects of the disorder and allow the disorder to be treated in the same way in all four structure determinations. Adjacent disordered atoms have been restrained to have similar U^ij components and the lengths of chemically equivalent bonds involving at least one disordered atom were also restrained to be similar. All H atoms were positioned geometrically and were allowed to ride on their parent atoms, with C—H = 0.93-0.98 Å and U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C).

Computing details

For all compounds, data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of (II) at room temperature (298 K), showing the 17.4 (5)% disorder (open bonds). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The molecular structure of (II) at 153 K. The disordered part [4.1 (5)%] has been excluded. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 3. A residual electron density map of (II) at 153 K in the O1A/N1A/N2A/O2A plane after refinement without disordered atoms. The first contour is at 0.6 e Å^-3 and the contour levels are at 0.05 e Å^-3.
	Fig. 4. The calculated geometry of the transition state for the `pedal motion' rearrangement of (II).

(II_298K) (2,2'-diazenediyldiphenolato-κ³O,N,O')dimethylsilicon

Crystal data

C14H14N2O2Si	Dx = 1.363 Mg m^−3
Mr = 270.36	Melting point: 388 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8884 reflections
a = 10.2295 (2) Å	θ = 2.4–32.8°
b = 8.0212 (1) Å	µ = 0.18 mm^−1
c = 32.1141 (5) Å	T = 298 K
V = 2635.05 (7) Å^3	Prism, red
Z = 8	0.45 × 0.18 × 0.15 mm
F(000) = 1136

Data collection

Bruker SMART CCD area-detector diffractometer	3192 independent reflections
Radiation source: sealed tube	2533 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
phi and ω scans	θmax = 28.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.921, Tmax = 0.978	k = −10→10
36746 measured reflections	l = −42→42

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0686P)^2 + 1.1914P] where P = (Fo^2 + 2Fc^2)/3
3192 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.41 e Å^−3
64 restraints	Δρmin = −0.26 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.

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	Occ. (<1)
Si1	−0.05587 (5)	0.49028 (7)	0.611223 (16)	0.03687 (17)
O1A	0.01393 (19)	0.4313 (4)	0.56499 (6)	0.0482 (8)	0.826 (3)
O2A	−0.0759 (2)	0.6800 (3)	0.63398 (7)	0.0475 (7)	0.826 (3)
N1A	0.15132 (19)	0.5509 (2)	0.62000 (6)	0.0360 (5)	0.826 (3)
N2A	0.21100 (19)	0.6315 (2)	0.64777 (6)	0.0389 (5)	0.826 (3)
O1B	0.0243 (8)	0.4838 (19)	0.5648 (2)	0.051 (3)	0.174 (3)
O2B	−0.0966 (6)	0.6486 (12)	0.6447 (3)	0.052 (2)	0.174 (3)
N1B	0.2313 (7)	0.5800 (10)	0.6269 (2)	0.0377 (15)	0.174 (3)
N2B	0.1166 (6)	0.6057 (9)	0.6404 (2)	0.0353 (14)	0.174 (3)
C1	0.2303 (2)	0.4782 (2)	0.58926 (6)	0.0408 (4)
C2	0.14540 (19)	0.4175 (3)	0.55925 (6)	0.0460 (5)
C3	0.1957 (2)	0.3430 (3)	0.52385 (7)	0.0563 (6)
H3	0.1400	0.3028	0.5033	0.068*
C4	0.3286 (2)	0.3291 (3)	0.51951 (7)	0.0561 (6)
H4	0.3625	0.2773	0.4959	0.067*
C5	0.4134 (2)	0.3903 (3)	0.54938 (7)	0.0517 (5)
H5	0.5032	0.3801	0.5457	0.062*
C6	0.3648 (2)	0.4661 (3)	0.58447 (6)	0.0449 (5)
H6	0.4210	0.5085	0.6046	0.054*
C7	0.1205 (2)	0.7199 (3)	0.67405 (6)	0.0444 (5)
C8	−0.0128 (2)	0.7462 (3)	0.66734 (6)	0.0477 (5)
C9	−0.0785 (2)	0.8562 (3)	0.69322 (8)	0.0576 (6)
H9	−0.1670	0.8764	0.6889	0.069*
C10	−0.0148 (3)	0.9360 (3)	0.72523 (7)	0.0572 (6)
H10	−0.0604	1.0090	0.7424	0.069*
C11	0.1167 (2)	0.9079 (3)	0.73191 (7)	0.0559 (6)
H11	0.1596	0.9613	0.7537	0.067*
C12	0.1835 (2)	0.8013 (3)	0.70645 (7)	0.0515 (5)
H12	0.2722	0.7832	0.7109	0.062*
C13	−0.0385 (2)	0.3207 (3)	0.65015 (6)	0.0440 (5)
H13A	−0.0404	0.3673	0.6777	0.066*
H13B	0.0431	0.2642	0.6459	0.066*
H13C	−0.1092	0.2430	0.6470	0.066*
C14	−0.2242 (2)	0.4840 (3)	0.58876 (7)	0.0478 (5)
H14A	−0.2356	0.5760	0.5700	0.072*
H14B	−0.2873	0.4914	0.6108	0.072*
H14C	−0.2363	0.3812	0.5739	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0305 (3)	0.0405 (3)	0.0396 (3)	−0.0028 (2)	−0.0039 (2)	0.0015 (2)
O1A	0.0339 (10)	0.068 (2)	0.0429 (10)	−0.0058 (10)	0.0027 (8)	0.0043 (9)
O2A	0.0566 (12)	0.0406 (11)	0.0452 (13)	0.0047 (9)	−0.0148 (9)	0.0000 (10)
N1A	0.0333 (10)	0.0385 (10)	0.0363 (10)	−0.0035 (8)	−0.0006 (8)	0.0042 (8)
N2A	0.0364 (10)	0.0429 (10)	0.0374 (10)	−0.0045 (8)	−0.0036 (8)	0.0001 (8)
O1B	0.036 (4)	0.063 (6)	0.055 (4)	−0.007 (4)	0.011 (3)	0.022 (4)
O2B	0.080 (4)	0.036 (4)	0.041 (4)	0.002 (4)	−0.024 (4)	0.007 (4)
N1B	0.040 (3)	0.039 (3)	0.033 (3)	0.000 (3)	0.000 (3)	0.001 (3)
N2B	0.036 (3)	0.036 (3)	0.034 (3)	0.000 (3)	0.002 (3)	0.000 (2)
C1	0.0469 (11)	0.0378 (9)	0.0376 (9)	0.0046 (8)	0.0079 (8)	0.0050 (8)
C2	0.0364 (10)	0.0594 (13)	0.0423 (10)	−0.0011 (9)	0.0046 (8)	0.0104 (9)
C3	0.0505 (13)	0.0774 (16)	0.0410 (11)	−0.0110 (12)	0.0004 (9)	−0.0035 (11)
C4	0.0561 (13)	0.0659 (14)	0.0462 (12)	0.0021 (11)	0.0118 (10)	−0.0097 (10)
C5	0.0387 (11)	0.0620 (14)	0.0543 (12)	0.0045 (10)	0.0088 (9)	0.0010 (11)
C6	0.0456 (11)	0.0463 (11)	0.0428 (10)	−0.0033 (9)	−0.0022 (9)	0.0008 (8)
C7	0.0567 (12)	0.0405 (10)	0.0360 (9)	−0.0012 (9)	0.0087 (9)	0.0020 (8)
C8	0.0640 (13)	0.0375 (10)	0.0417 (11)	−0.0019 (9)	−0.0092 (10)	−0.0007 (8)
C9	0.0521 (13)	0.0576 (13)	0.0630 (14)	0.0068 (11)	−0.0027 (11)	−0.0065 (11)
C10	0.0664 (15)	0.0577 (13)	0.0474 (12)	0.0040 (12)	0.0118 (11)	−0.0131 (10)
C11	0.0620 (15)	0.0617 (14)	0.0441 (11)	−0.0125 (11)	0.0028 (11)	−0.0101 (10)
C12	0.0473 (12)	0.0563 (12)	0.0510 (12)	−0.0087 (10)	0.0057 (10)	0.0013 (10)
C13	0.0391 (10)	0.0458 (11)	0.0472 (11)	−0.0004 (8)	0.0020 (9)	0.0059 (9)
C14	0.0346 (10)	0.0549 (12)	0.0539 (12)	−0.0021 (9)	−0.0079 (9)	0.0002 (10)

Geometric parameters (Å, º)

Si1—O2A	1.7006 (19)	C3—H3	0.9300
Si1—O1B	1.704 (4)	C4—C5	1.384 (3)
Si1—O1A	1.7142 (19)	C4—H4	0.9300
Si1—O2B	1.715 (4)	C5—C6	1.373 (3)
Si1—C13	1.856 (2)	C5—H5	0.9300
Si1—C14	1.868 (2)	C6—H6	0.9300
Si1—N1A	2.193 (2)	C7—C12	1.388 (3)
Si1—N2B	2.203 (5)	C7—C8	1.396 (3)
O1A—C2	1.362 (3)	C8—C9	1.386 (3)
O2A—C8	1.359 (3)	C9—C10	1.375 (3)
N1A—N2A	1.260 (3)	C9—H9	0.9300
N1A—C1	1.402 (3)	C10—C11	1.381 (4)
N2A—C7	1.440 (3)	C10—H10	0.9300
O1B—C2	1.360 (4)	C11—C12	1.366 (3)
O2B—C8	1.370 (4)	C11—H11	0.9300
N1B—N2B	1.269 (5)	C12—H12	0.9300
N1B—C1	1.458 (5)	C13—H13A	0.9600
N2B—C7	1.416 (5)	C13—H13B	0.9600
N2B—C8	1.941 (7)	C13—H13C	0.9600
C1—C2	1.385 (3)	C14—H14A	0.9600
C1—C6	1.388 (3)	C14—H14B	0.9600
C2—C3	1.384 (3)	C14—H14C	0.9600
C3—C4	1.371 (3)
O2A—Si1—O1B	117.5 (6)	C4—C3—C2	119.2 (2)
O2A—Si1—O1A	132.03 (13)	C4—C3—H3	120.4
O1B—Si1—O2B	133.5 (7)	C2—C3—H3	120.4
O1A—Si1—O2B	148.0 (4)	C3—C4—C5	121.5 (2)
O2A—Si1—C13	112.20 (11)	C3—C4—H4	119.3
O1B—Si1—C13	121.4 (4)	C5—C4—H4	119.3
O1A—Si1—C13	109.95 (12)	C6—C5—C4	119.9 (2)
O2B—Si1—C13	98.3 (5)	C6—C5—H5	120.0
O2A—Si1—C14	94.55 (10)	C4—C5—H5	120.0
O1B—Si1—C14	96.0 (3)	C5—C6—C1	118.7 (2)
O1A—Si1—C14	92.41 (10)	C5—C6—H6	120.6
O2B—Si1—C14	92.2 (2)	C1—C6—H6	120.6
C13—Si1—C14	109.18 (10)	C12—C7—C8	119.90 (19)
O2A—Si1—N1A	82.11 (9)	C12—C7—N2B	152.7 (3)
O1B—Si1—N1A	69.8 (4)	C8—C7—N2B	87.3 (3)
O1A—Si1—N1A	76.70 (9)	C12—C7—N2A	111.86 (19)
O2B—Si1—N1A	89.4 (2)	C8—C7—N2A	127.74 (18)
C13—Si1—N1A	89.04 (8)	O2A—C8—C9	119.4 (2)
C14—Si1—N1A	161.24 (9)	O2B—C8—C9	112.3 (3)
O2A—Si1—N2B	62.43 (19)	O2A—C8—C7	121.8 (2)
O1B—Si1—N2B	90.0 (5)	O2B—C8—C7	127.3 (3)
O1A—Si1—N2B	98.70 (18)	C9—C8—C7	118.50 (19)
O2B—Si1—N2B	67.4 (3)	O2A—C8—N2B	75.3 (2)
C13—Si1—N2B	86.8 (2)	O2B—C8—N2B	81.9 (3)
C14—Si1—N2B	156.1 (2)	C9—C8—N2B	165.3 (2)
C2—O1A—Si1	123.43 (17)	C7—C8—N2B	46.78 (16)
C8—O2A—Si1	129.15 (17)	C10—C9—C8	121.0 (2)
N2A—N1A—C1	115.65 (19)	C10—C9—H9	119.5
N2A—N1A—Si1	132.32 (16)	C8—C9—H9	119.5
C1—N1A—Si1	111.97 (14)	C9—C10—C11	120.1 (2)
N1A—N2A—C7	110.87 (18)	C9—C10—H10	119.9
C2—O1B—Si1	124.4 (4)	C11—C10—H10	119.9
C8—O2B—Si1	127.1 (5)	C12—C11—C10	119.8 (2)
N2B—N1B—C1	111.6 (5)	C12—C11—H11	120.1
N1B—N2B—C7	110.0 (4)	C10—C11—H11	120.1
N1B—N2B—C8	151.4 (5)	C11—C12—C7	120.7 (2)
C7—N2B—C8	45.9 (2)	C11—C12—H12	119.6
N1B—N2B—Si1	121.8 (4)	C7—C12—H12	119.6
C7—N2B—Si1	128.2 (4)	Si1—C13—H13A	109.5
C8—N2B—Si1	83.5 (2)	Si1—C13—H13B	109.5
C2—C1—C6	121.30 (18)	H13A—C13—H13B	109.5
C2—C1—N1A	105.95 (18)	Si1—C13—H13C	109.5
C6—C1—N1A	132.7 (2)	H13A—C13—H13C	109.5
C2—C1—N1B	141.1 (3)	H13B—C13—H13C	109.5
C6—C1—N1B	97.1 (3)	Si1—C14—H14A	109.5
O1B—C2—C3	127.9 (5)	Si1—C14—H14B	109.5
O1A—C2—C3	120.9 (2)	H14A—C14—H14B	109.5
O1B—C2—C1	110.1 (6)	Si1—C14—H14C	109.5
O1A—C2—C1	119.7 (2)	H14A—C14—H14C	109.5
C3—C2—C1	119.38 (18)	H14B—C14—H14C	109.5
O2A—Si1—O1A—C2	78.9 (3)	N2B—N1B—C1—N1A	−1.4 (5)
O1B—Si1—O1A—C2	72.5 (11)	Si1—O1B—C2—O1A	76.5 (10)
O2B—Si1—O1A—C2	79.2 (5)	Si1—O1B—C2—C3	150.2 (7)
C13—Si1—O1A—C2	−71.4 (3)	Si1—O1B—C2—C1	−48.7 (14)
C14—Si1—O1A—C2	177.2 (2)	Si1—O1A—C2—O1B	−72.9 (10)
N1A—Si1—O1A—C2	12.7 (2)	Si1—O1A—C2—C3	169.0 (2)
N2B—Si1—O1A—C2	18.4 (3)	Si1—O1A—C2—C1	−10.8 (4)
O1B—Si1—O2A—C8	−105.4 (4)	C6—C1—C2—O1B	−162.8 (6)
O1A—Si1—O2A—C8	−107.2 (3)	N1A—C1—C2—O1B	14.8 (6)
O2B—Si1—O2A—C8	73.4 (10)	N1B—C1—C2—O1B	6.4 (9)
C13—Si1—O2A—C8	42.6 (3)	C6—C1—C2—O1A	179.9 (2)
C14—Si1—O2A—C8	155.4 (3)	N1A—C1—C2—O1A	−2.4 (3)
N1A—Si1—O2A—C8	−43.2 (3)	N1B—C1—C2—O1A	−10.8 (7)
N2B—Si1—O2A—C8	−31.1 (3)	C6—C1—C2—C3	0.2 (3)
O2A—Si1—N1A—N2A	33.2 (2)	N1A—C1—C2—C3	177.8 (2)
O1B—Si1—N1A—N2A	156.4 (5)	N1B—C1—C2—C3	169.4 (6)
O1A—Si1—N1A—N2A	169.8 (2)	O1B—C2—C3—C4	160.4 (8)
O2B—Si1—N1A—N2A	18.9 (5)	O1A—C2—C3—C4	−179.0 (2)
C13—Si1—N1A—N2A	−79.4 (2)	C1—C2—C3—C4	0.8 (4)
C14—Si1—N1A—N2A	114.0 (3)	C2—C3—C4—C5	−1.1 (4)
N2B—Si1—N1A—N2A	4.6 (6)	C3—C4—C5—C6	0.4 (4)
O2A—Si1—N1A—C1	−149.94 (16)	C4—C5—C6—C1	0.6 (3)
O1B—Si1—N1A—C1	−26.7 (5)	C2—C1—C6—C5	−0.8 (3)
O1A—Si1—N1A—C1	−13.28 (16)	N1A—C1—C6—C5	−177.8 (2)
O2B—Si1—N1A—C1	−164.2 (5)	N1B—C1—C6—C5	−174.0 (4)
C13—Si1—N1A—C1	97.49 (15)	N1B—N2B—C7—C12	−21.9 (14)
C14—Si1—N1A—C1	−69.1 (3)	C8—N2B—C7—C12	176.5 (8)
N2B—Si1—N1A—C1	−178.5 (7)	Si1—N2B—C7—C12	160.8 (4)
C1—N1A—N2A—C7	171.76 (17)	N1B—N2B—C7—C8	161.6 (7)
Si1—N1A—N2A—C7	−11.4 (3)	Si1—N2B—C7—C8	−15.7 (6)
O2A—Si1—O1B—C2	110.4 (12)	N1B—N2B—C7—N2A	−5.7 (5)
O1A—Si1—O1B—C2	−75.0 (10)	C8—N2B—C7—N2A	−167.3 (5)
O2B—Si1—O1B—C2	109.9 (11)	Si1—N2B—C7—N2A	177.0 (10)
C13—Si1—O1B—C2	−34.4 (16)	N1A—N2A—C7—C12	176.29 (19)
C14—Si1—O1B—C2	−151.3 (12)	N1A—N2A—C7—C8	−12.0 (3)
N1A—Si1—O1B—C2	41.3 (11)	N1A—N2A—C7—N2B	4.2 (6)
N2B—Si1—O1B—C2	51.8 (13)	Si1—O2A—C8—O2B	−74.5 (10)
O2A—Si1—O2B—C8	−67.6 (9)	Si1—O2A—C8—C9	−148.5 (2)
O1B—Si1—O2B—C8	−66.1 (13)	Si1—O2A—C8—C7	38.1 (4)
O1A—Si1—O2B—C8	−68.4 (14)	Si1—O2A—C8—N2B	32.5 (3)
C13—Si1—O2B—C8	83.8 (11)	Si1—O2B—C8—O2A	68.4 (8)
C14—Si1—O2B—C8	−166.5 (10)	Si1—O2B—C8—C9	−176.4 (8)
N1A—Si1—O2B—C8	−5.2 (11)	Si1—O2B—C8—C7	−12.5 (14)
N2B—Si1—O2B—C8	0.7 (9)	Si1—O2B—C8—N2B	−0.7 (10)
C1—N1B—N2B—C7	−173.5 (6)	C12—C7—C8—O2A	174.4 (2)
C1—N1B—N2B—C8	−145.1 (11)	N2B—C7—C8—O2A	−7.4 (4)
C1—N1B—N2B—Si1	4.1 (11)	N2A—C7—C8—O2A	3.3 (3)
O2A—Si1—N2B—N1B	−149.3 (9)	C12—C7—C8—O2B	−162.1 (7)
O1B—Si1—N2B—N1B	−27.9 (9)	N2B—C7—C8—O2B	16.1 (8)
O1A—Si1—N2B—N1B	−16.1 (8)	N2A—C7—C8—O2B	26.8 (8)
O2B—Si1—N2B—N1B	−166.1 (10)	C12—C7—C8—C9	0.9 (3)
C13—Si1—N2B—N1B	93.6 (8)	N2B—C7—C8—C9	179.1 (4)
C14—Si1—N2B—N1B	−133.0 (6)	N2A—C7—C8—C9	−170.2 (2)
N1A—Si1—N2B—N1B	−1.6 (5)	C12—C7—C8—N2B	−178.1 (4)
O2A—Si1—N2B—C7	27.7 (6)	N2A—C7—C8—N2B	10.7 (4)
O1B—Si1—N2B—C7	149.1 (8)	N1B—N2B—C8—O2A	135.1 (15)
O1A—Si1—N2B—C7	160.9 (6)	C7—N2B—C8—O2A	173.5 (4)
O2B—Si1—N2B—C7	10.9 (7)	Si1—N2B—C8—O2A	−18.90 (19)
C13—Si1—N2B—C7	−89.4 (7)	N1B—N2B—C8—O2B	154.5 (16)
C14—Si1—N2B—C7	44.1 (11)	C7—N2B—C8—O2B	−167.2 (7)
N1A—Si1—N2B—C7	175.5 (12)	Si1—N2B—C8—O2B	0.5 (6)
O2A—Si1—N2B—C8	16.41 (17)	N1B—N2B—C8—C9	−42 (2)
O1B—Si1—N2B—C8	137.8 (5)	C7—N2B—C8—C9	−3.2 (14)
O1A—Si1—N2B—C8	149.6 (2)	Si1—N2B—C8—C9	164.4 (11)
O2B—Si1—N2B—C8	−0.4 (5)	N1B—N2B—C8—C7	−38.4 (13)
C13—Si1—N2B—C8	−100.7 (3)	Si1—N2B—C8—C7	167.6 (5)
C14—Si1—N2B—C8	32.8 (7)	O2A—C8—C9—C10	−174.7 (2)
N1A—Si1—N2B—C8	164.2 (8)	O2B—C8—C9—C10	164.5 (6)
N2A—N1A—C1—C2	−171.73 (19)	C7—C8—C9—C10	−1.0 (4)
Si1—N1A—C1—C2	10.81 (19)	N2B—C8—C9—C10	1.6 (14)
N2A—N1A—C1—C6	5.6 (3)	C8—C9—C10—C11	0.3 (4)
Si1—N1A—C1—C6	−171.91 (19)	C9—C10—C11—C12	0.4 (4)
N2A—N1A—C1—N1B	−0.8 (6)	C10—C11—C12—C7	−0.5 (4)
Si1—N1A—C1—N1B	−178.2 (7)	C8—C7—C12—C11	−0.2 (3)
N2B—N1B—C1—C2	12.6 (12)	N2B—C7—C12—C11	−176.2 (8)
N2B—N1B—C1—C6	−176.7 (7)	N2A—C7—C12—C11	172.3 (2)

(II_153K) (2,2'-diazenediyldiphenolato-κ³O,N,O')dimethylsilicon

Crystal data

C14H14N2O2Si	Dx = 1.414 Mg m^−3
Mr = 270.36	Melting point: 388 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6360 reflections
a = 10.0440 (11) Å	θ = 2.4–32.8°
b = 7.8990 (8) Å	µ = 0.18 mm^−1
c = 32.011 (3) Å	T = 153 K
V = 2539.7 (4) Å^3	Prism, red
Z = 8	0.45 × 0.18 × 0.15 mm
F(000) = 1136

Data collection

Bruker SMART CCD area-detector diffractometer	3063 independent reflections
Radiation source: sealed tube	2632 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
phi and ω scans	θmax = 28.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.921, Tmax = 0.978	k = −10→9
16295 measured reflections	l = −33→42

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0492P)^2 + 1.3714P] where P = (Fo^2 + 2Fc^2)/3
3063 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.36 e Å^−3
64 restraints	Δρmin = −0.35 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.

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	Occ. (<1)
Si1	−0.05676 (4)	0.50369 (5)	0.610595 (12)	0.01956 (12)
O1A	0.00991 (11)	0.44411 (18)	0.56357 (4)	0.0259 (4)	0.959 (2)
O2A	−0.07468 (12)	0.69447 (15)	0.63462 (4)	0.0240 (3)	0.959 (2)
N1A	0.15219 (12)	0.56168 (16)	0.61944 (4)	0.0198 (3)	0.959 (2)
N2A	0.21294 (12)	0.64156 (16)	0.64783 (4)	0.0213 (3)	0.959 (2)
O1B	0.0209 (19)	0.494 (5)	0.5632 (3)	0.027 (3)	0.041 (2)
O2B	−0.0921 (8)	0.666 (3)	0.6443 (10)	0.025 (3)	0.041 (2)
N1B	0.2248 (12)	0.582 (3)	0.6252 (5)	0.0208 (18)	0.041 (2)
N2B	0.1132 (8)	0.622 (3)	0.6408 (6)	0.0200 (18)	0.041 (2)
C1	0.22756 (14)	0.48552 (18)	0.58821 (4)	0.0213 (3)
C2	0.14202 (13)	0.4242 (2)	0.55770 (5)	0.0236 (3)
C3	0.19385 (15)	0.3488 (2)	0.52216 (5)	0.0282 (3)
H3	0.1366	0.3072	0.5009	0.034*
C4	0.33054 (16)	0.3350 (2)	0.51826 (5)	0.0284 (3)
H4	0.3669	0.2819	0.4942	0.034*
C5	0.41585 (14)	0.3974 (2)	0.54883 (5)	0.0262 (3)
H5	0.5094	0.3866	0.5454	0.031*
C6	0.36544 (14)	0.47450 (19)	0.58393 (5)	0.0231 (3)
H6	0.4231	0.5191	0.6047	0.028*
C7	0.12824 (14)	0.73266 (18)	0.67449 (4)	0.0224 (3)
C8	−0.00788 (14)	0.76180 (19)	0.66708 (4)	0.0234 (3)
C9	−0.07545 (15)	0.8739 (2)	0.69311 (5)	0.0288 (3)
H9	−0.1670	0.8968	0.6882	0.035*
C10	−0.01127 (16)	0.9521 (2)	0.72596 (5)	0.0289 (3)
H10	−0.0590	1.0279	0.7435	0.035*
C11	0.12279 (16)	0.9209 (2)	0.73362 (5)	0.0281 (3)
H11	0.1664	0.9738	0.7565	0.034*
C12	0.19143 (15)	0.8130 (2)	0.70788 (5)	0.0256 (3)
H12	0.2833	0.7926	0.7128	0.031*
C13	−0.04038 (14)	0.3325 (2)	0.65013 (5)	0.0239 (3)
H13A	−0.0344	0.3825	0.6781	0.036*
H13B	0.0403	0.2666	0.6445	0.036*
H13C	−0.1183	0.2581	0.6487	0.036*
C14	−0.22992 (14)	0.5036 (2)	0.58927 (5)	0.0257 (3)
H14A	−0.2438	0.6057	0.5724	0.039*
H14B	−0.2938	0.5019	0.6124	0.039*
H14C	−0.2429	0.4031	0.5718	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.01493 (19)	0.0221 (2)	0.0216 (2)	−0.00128 (13)	−0.00120 (13)	0.00041 (16)
O1A	0.0162 (5)	0.0379 (9)	0.0236 (6)	−0.0021 (5)	0.0010 (4)	−0.0008 (5)
O2A	0.0229 (5)	0.0228 (6)	0.0263 (7)	0.0024 (4)	−0.0050 (4)	−0.0011 (5)
N1A	0.0165 (6)	0.0211 (6)	0.0217 (6)	−0.0018 (5)	−0.0008 (5)	0.0021 (5)
N2A	0.0201 (6)	0.0222 (6)	0.0217 (6)	−0.0017 (5)	−0.0013 (5)	0.0013 (5)
O1B	0.017 (5)	0.038 (5)	0.027 (5)	−0.003 (5)	0.003 (5)	0.006 (5)
O2B	0.032 (5)	0.020 (5)	0.023 (5)	0.001 (5)	−0.010 (5)	−0.002 (5)
N1B	0.021 (3)	0.022 (3)	0.020 (3)	−0.001 (3)	0.001 (3)	0.001 (3)
N2B	0.018 (3)	0.022 (3)	0.020 (3)	−0.001 (3)	0.001 (3)	0.001 (3)
C1	0.0232 (7)	0.0200 (7)	0.0206 (7)	0.0014 (5)	0.0025 (5)	0.0028 (6)
C2	0.0175 (6)	0.0289 (8)	0.0243 (7)	−0.0010 (5)	0.0013 (5)	0.0050 (6)
C3	0.0245 (7)	0.0373 (8)	0.0228 (7)	−0.0044 (6)	−0.0004 (6)	−0.0026 (7)
C4	0.0268 (7)	0.0333 (8)	0.0251 (7)	0.0011 (6)	0.0053 (6)	−0.0032 (7)
C5	0.0195 (6)	0.0296 (8)	0.0296 (8)	0.0021 (6)	0.0028 (6)	0.0021 (6)
C6	0.0212 (6)	0.0229 (7)	0.0252 (7)	−0.0006 (5)	−0.0018 (5)	0.0015 (6)
C7	0.0254 (7)	0.0194 (7)	0.0222 (7)	−0.0013 (5)	0.0029 (5)	0.0019 (6)
C8	0.0267 (7)	0.0202 (7)	0.0234 (7)	−0.0015 (6)	−0.0008 (6)	0.0024 (6)
C9	0.0261 (7)	0.0301 (8)	0.0303 (8)	0.0034 (6)	0.0008 (6)	−0.0003 (7)
C10	0.0320 (8)	0.0291 (8)	0.0256 (8)	0.0024 (6)	0.0062 (6)	−0.0047 (6)
C11	0.0320 (8)	0.0290 (8)	0.0233 (7)	−0.0068 (6)	0.0008 (6)	−0.0027 (6)
C12	0.0232 (6)	0.0271 (7)	0.0264 (7)	−0.0044 (6)	0.0016 (6)	0.0023 (6)
C13	0.0214 (6)	0.0249 (7)	0.0253 (7)	−0.0008 (5)	0.0007 (5)	0.0014 (6)
C14	0.0175 (6)	0.0308 (8)	0.0288 (8)	−0.0018 (5)	−0.0026 (5)	0.0002 (7)

Geometric parameters (Å, º)

Si1—O2A	1.7014 (12)	C3—H3	0.9500
Si1—O1B	1.707 (4)	C4—C5	1.391 (2)
Si1—O2B	1.710 (4)	C4—H4	0.9500
Si1—O1A	1.7136 (12)	C5—C6	1.375 (2)
Si1—C13	1.8594 (15)	C5—H5	0.9500
Si1—C14	1.8684 (15)	C6—H6	0.9500
Si1—N1A	2.1666 (13)	C7—C12	1.395 (2)
Si1—N2B	2.172 (5)	C7—C8	1.407 (2)
O1A—C2	1.3493 (16)	C8—C9	1.392 (2)
O2A—C8	1.3463 (17)	C9—C10	1.379 (2)
N1A—N2A	1.2635 (18)	C9—H9	0.9500
N1A—C1	1.3910 (18)	C10—C11	1.391 (2)
N2A—C7	1.4035 (19)	C10—H10	0.9500
O1B—C2	1.348 (5)	C11—C12	1.372 (2)
O2B—C8	1.351 (5)	C11—H11	0.9500
N1B—N2B	1.267 (5)	C12—H12	0.9500
N1B—C1	1.409 (5)	C13—H13A	0.9800
N2B—C7	1.397 (5)	C13—H13B	0.9800
N2B—C8	1.846 (11)	C13—H13C	0.9800
C1—C2	1.388 (2)	C14—H14A	0.9800
C1—C6	1.394 (2)	C14—H14B	0.9800
C2—C3	1.386 (2)	C14—H14C	0.9800
C3—C4	1.383 (2)
O2A—Si1—O1B	119.2 (14)	C4—C3—C2	118.74 (14)
O1B—Si1—O2B	133.4 (19)	C4—C3—H3	120.6
O2A—Si1—O1A	132.98 (6)	C2—C3—H3	120.6
O2B—Si1—O1A	147.2 (13)	C3—C4—C5	121.36 (15)
O2A—Si1—C13	110.23 (7)	C3—C4—H4	119.3
O1B—Si1—C13	122.2 (9)	C5—C4—H4	119.3
O2B—Si1—C13	97.7 (14)	C6—C5—C4	120.33 (13)
O1A—Si1—C13	111.32 (7)	C6—C5—H5	119.8
O2A—Si1—C14	93.85 (6)	C4—C5—H5	119.8
O1B—Si1—C14	95.8 (7)	C5—C6—C1	118.28 (14)
O2B—Si1—C14	92.1 (4)	C5—C6—H6	120.9
O1A—Si1—C14	92.44 (6)	C1—C6—H6	120.9
C13—Si1—C14	109.31 (7)	C12—C7—N2B	157.7 (6)
O2A—Si1—N1A	81.73 (5)	C12—C7—N2A	115.03 (13)
O1B—Si1—N1A	71.5 (10)	C12—C7—C8	119.79 (13)
O2B—Si1—N1A	87.7 (3)	N2B—C7—C8	82.3 (5)
O1A—Si1—N1A	78.13 (5)	N2A—C7—C8	124.78 (13)
C13—Si1—N1A	88.80 (6)	O2A—C8—C9	118.04 (13)
C14—Si1—N1A	161.72 (6)	O2B—C8—C9	112.1 (3)
O2A—Si1—N2B	60.1 (4)	O2A—C8—C7	123.37 (13)
O1B—Si1—N2B	93.1 (13)	O2B—C8—C7	127.4 (5)
O2B—Si1—N2B	64.0 (4)	C9—C8—C7	118.48 (14)
O1A—Si1—N2B	101.6 (3)	O2A—C8—N2B	74.9 (3)
C13—Si1—N2B	86.6 (8)	O2B—C8—N2B	80.2 (3)
C14—Si1—N2B	153.4 (5)	C9—C8—N2B	167.0 (3)
C2—O1A—Si1	122.59 (10)	C7—C8—N2B	48.6 (2)
C8—O2A—Si1	130.24 (10)	C10—C9—C8	120.88 (14)
N2A—N1A—C1	118.04 (12)	C10—C9—H9	119.6
N2A—N1A—Si1	131.87 (10)	C8—C9—H9	119.6
C1—N1A—Si1	109.99 (9)	C9—C10—C11	120.50 (15)
N1A—N2A—C7	113.62 (12)	C9—C10—H10	119.7
C2—O1B—Si1	123.1 (4)	C11—C10—H10	119.7
C8—O2B—Si1	129.1 (5)	C12—C11—C10	119.39 (15)
N2B—N1B—C1	118.9 (8)	C12—C11—H11	120.3
N1B—N2B—C7	111.3 (4)	C10—C11—H11	120.3
N1B—N2B—C8	155.7 (15)	C11—C12—C7	120.94 (14)
C7—N2B—C8	49.1 (3)	C11—C12—H12	119.5
N1B—N2B—Si1	114.4 (6)	C7—C12—H12	119.5
C7—N2B—Si1	134.2 (6)	Si1—C13—H13A	109.5
C8—N2B—Si1	86.7 (4)	Si1—C13—H13B	109.5
C2—C1—N1A	108.65 (12)	H13A—C13—H13B	109.5
C2—C1—C6	121.59 (13)	Si1—C13—H13C	109.5
N1A—C1—C6	129.66 (14)	H13A—C13—H13C	109.5
C2—C1—N1B	140.2 (5)	H13B—C13—H13C	109.5
C6—C1—N1B	97.8 (5)	Si1—C14—H14A	109.5
O1B—C2—C3	128.6 (9)	Si1—C14—H14B	109.5
O1A—C2—C3	122.26 (13)	H14A—C14—H14B	109.5
O1B—C2—C1	108.8 (14)	Si1—C14—H14C	109.5
O1A—C2—C1	118.04 (13)	H14A—C14—H14C	109.5
C3—C2—C1	119.68 (13)	H14B—C14—H14C	109.5
O2A—Si1—O1A—C2	80.95 (15)	N2B—N1B—C1—C6	−180 (3)
O1B—Si1—O1A—C2	74.1 (18)	Si1—O1B—C2—O1A	77.0 (18)
O2B—Si1—O1A—C2	80.7 (10)	Si1—O1B—C2—C3	152.1 (17)
C13—Si1—O1A—C2	−69.66 (14)	Si1—O1B—C2—C1	−48 (3)
C14—Si1—O1A—C2	178.51 (14)	Si1—O1A—C2—O1B	−74.7 (16)
N1A—Si1—O1A—C2	14.32 (13)	Si1—O1A—C2—C3	168.68 (13)
N2B—Si1—O1A—C2	21.2 (8)	Si1—O1A—C2—C1	−12.8 (2)
O1B—Si1—O2A—C8	−103.9 (6)	N1A—C1—C2—O1B	15.0 (14)
O2B—Si1—O2A—C8	74 (2)	C6—C1—C2—O1B	−161.7 (14)
O1A—Si1—O2A—C8	−105.72 (15)	N1B—C1—C2—O1B	9 (2)
C13—Si1—O2A—C8	45.12 (16)	N1A—C1—C2—O1A	−1.36 (19)
C14—Si1—O2A—C8	157.33 (14)	C6—C1—C2—O1A	−178.07 (14)
N1A—Si1—O2A—C8	−40.52 (14)	N1B—C1—C2—O1A	−7.3 (19)
N2B—Si1—O2A—C8	−28.3 (8)	N1A—C1—C2—C3	177.24 (14)
O2A—Si1—N1A—N2A	32.67 (14)	C6—C1—C2—C3	0.5 (2)
O1B—Si1—N1A—N2A	157.4 (12)	N1B—C1—C2—C3	171.3 (19)
O2B—Si1—N1A—N2A	19.7 (14)	O1B—C2—C3—C4	159 (2)
O1A—Si1—N1A—N2A	169.93 (15)	O1A—C2—C3—C4	179.18 (15)
C13—Si1—N1A—N2A	−77.98 (14)	C1—C2—C3—C4	0.6 (2)
C14—Si1—N1A—N2A	109.7 (2)	C2—C3—C4—C5	−0.9 (3)
N2B—Si1—N1A—N2A	6.5 (19)	C3—C4—C5—C6	0.1 (3)
O2A—Si1—N1A—C1	−151.17 (10)	C4—C5—C6—C1	1.1 (2)
O1B—Si1—N1A—C1	−26.5 (12)	C2—C1—C6—C5	−1.4 (2)
O2B—Si1—N1A—C1	−164.1 (14)	N1A—C1—C6—C5	−177.35 (14)
O1A—Si1—N1A—C1	−13.91 (10)	N1B—C1—C6—C5	−175.5 (12)
C13—Si1—N1A—C1	98.18 (10)	N1B—N2B—C7—C12	−23 (5)
C14—Si1—N1A—C1	−74.1 (2)	C8—N2B—C7—C12	174 (3)
N2B—Si1—N1A—C1	−177.3 (19)	Si1—N2B—C7—C12	155.8 (6)
C1—N1A—N2A—C7	171.79 (12)	N1B—N2B—C7—N2A	−4.6 (16)
Si1—N1A—N2A—C7	−12.29 (19)	C8—N2B—C7—N2A	−167.7 (14)
O2A—Si1—O1B—C2	110 (3)	Si1—N2B—C7—N2A	174 (4)
O2B—Si1—O1B—C2	109 (3)	N1B—N2B—C7—C8	163 (3)
O1A—Si1—O1B—C2	−75.6 (19)	Si1—N2B—C7—C8	−18 (2)
C13—Si1—O1B—C2	−35 (4)	N1A—N2A—C7—C12	175.84 (13)
C14—Si1—O1B—C2	−152 (3)	N1A—N2A—C7—N2B	3.4 (17)
N1A—Si1—O1B—C2	41 (3)	N1A—N2A—C7—C8	−11.4 (2)
N2B—Si1—O1B—C2	53 (3)	Si1—O2A—C8—O2B	−75 (2)
O2A—Si1—O2B—C8	−70.3 (18)	Si1—O2A—C8—C9	−149.68 (13)
O1B—Si1—O2B—C8	−67 (4)	Si1—O2A—C8—C7	34.3 (2)
O1A—Si1—O2B—C8	−70 (4)	Si1—O2A—C8—N2B	30.1 (9)
C13—Si1—O2B—C8	83 (3)	Si1—O2B—C8—O2A	70.9 (16)
C14—Si1—O2B—C8	−168 (3)	Si1—O2B—C8—C9	−176 (2)
N1A—Si1—O2B—C8	−6 (3)	Si1—O2B—C8—C7	−13 (4)
N2B—Si1—O2B—C8	0 (3)	Si1—O2B—C8—N2B	0 (3)
C1—N1B—N2B—C7	−173.4 (19)	C12—C7—C8—O2A	177.31 (14)
C1—N1B—N2B—C8	−141 (4)	N2B—C7—C8—O2A	−5.4 (12)
C1—N1B—N2B—Si1	7 (4)	N2A—C7—C8—O2A	4.9 (2)
O2A—Si1—N2B—N1B	−152 (3)	C12—C7—C8—O2B	−161 (2)
O1B—Si1—N2B—N1B	−30 (3)	N2B—C7—C8—O2B	16 (2)
O2B—Si1—N2B—N1B	−168 (3)	N2A—C7—C8—O2B	26 (2)
O1A—Si1—N2B—N1B	−19 (2)	C12—C7—C8—C9	1.3 (2)
C13—Si1—N2B—N1B	92 (2)	N2B—C7—C8—C9	178.6 (12)
C14—Si1—N2B—N1B	−139.5 (17)	N2A—C7—C8—C9	−171.13 (14)
N1A—Si1—N2B—N1B	−2.5 (15)	C12—C7—C8—N2B	−177.3 (12)
O2A—Si1—N2B—C7	29 (2)	N2A—C7—C8—N2B	10.3 (12)
O1B—Si1—N2B—C7	151 (3)	N1B—N2B—C8—O2A	134 (5)
O2B—Si1—N2B—C7	13 (3)	C7—N2B—C8—O2A	175.4 (10)
O1A—Si1—N2B—C7	162 (2)	Si1—N2B—C8—O2A	−17.5 (5)
C13—Si1—N2B—C7	−87 (2)	N1B—N2B—C8—O2B	152 (6)
C14—Si1—N2B—C7	42 (4)	C7—N2B—C8—O2B	−167 (2)
N1A—Si1—N2B—C7	179 (4)	Si1—N2B—C8—O2B	0.2 (19)
O2A—Si1—N2B—C8	15.4 (5)	N1B—N2B—C8—C9	−47 (9)
O1B—Si1—N2B—C8	137.6 (12)	C7—N2B—C8—C9	−6 (5)
O2B—Si1—N2B—C8	−0.1 (16)	Si1—N2B—C8—C9	162 (3)
O1A—Si1—N2B—C8	148.6 (7)	N1B—N2B—C8—C7	−41 (5)
C13—Si1—N2B—C8	−100.4 (8)	Si1—N2B—C8—C7	167.2 (15)
C14—Si1—N2B—C8	28 (2)	O2A—C8—C9—C10	−177.53 (15)
N1A—Si1—N2B—C8	165 (3)	O2B—C8—C9—C10	163.7 (19)
N2A—N1A—C1—C2	−172.43 (13)	C7—C8—C9—C10	−1.3 (2)
Si1—N1A—C1—C2	10.81 (14)	N2B—C8—C9—C10	3 (4)
N2A—N1A—C1—C6	3.9 (2)	C8—C9—C10—C11	0.2 (2)
Si1—N1A—C1—C6	−172.83 (13)	C9—C10—C11—C12	0.8 (2)
N2A—N1A—C1—N1B	0 (2)	C10—C11—C12—C7	−0.8 (2)
Si1—N1A—C1—N1B	−176 (2)	N2B—C7—C12—C11	−173 (3)
N2B—N1B—C1—C2	8 (4)	N2A—C7—C12—C11	172.88 (14)
N2B—N1B—C1—N1A	−2.6 (15)	C8—C7—C12—C11	−0.2 (2)

(II_93K_flash_cooled) (2,2'-diazenediyldiphenolato-κ³O,N,O')dimethylsilicon

Crystal data

C14H14N2O2Si	Dx = 1.410 Mg m^−3
Mr = 270.36	Melting point: 388 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6113 reflections
a = 10.0654 (5) Å	θ = 2.4–32.5°
b = 7.9069 (4) Å	µ = 0.18 mm^−1
c = 31.9971 (17) Å	T = 93 K
V = 2546.5 (2) Å^3	Prism, red
Z = 8	0.45 × 0.18 × 0.15 mm
F(000) = 1136

Data collection

Bruker SMART CCD area-detector diffractometer	2937 independent reflections
Radiation source: sealed tube	2606 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
phi and ω scans	θmax = 28.0°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.921, Tmax = 0.978	k = −9→10
13356 measured reflections	l = −42→26

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0386P)^2 + 2.2636P] where P = (Fo^2 + 2Fc^2)/3
2937 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.44 e Å^−3
64 restraints	Δρmin = −0.29 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.

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	Occ. (<1)
Si1	−0.05829 (4)	0.50647 (6)	0.611185 (13)	0.01408 (12)
O1A	0.00893 (19)	0.4462 (3)	0.56353 (7)	0.0172 (4)	0.866 (3)
O2A	−0.07681 (17)	0.6965 (2)	0.63499 (5)	0.0163 (4)	0.866 (3)
N1A	0.15084 (14)	0.5667 (2)	0.61963 (4)	0.0133 (3)	0.866 (3)
N2A	0.21203 (14)	0.64793 (19)	0.64779 (5)	0.0147 (3)	0.866 (3)
O1B	0.0257 (13)	0.4959 (18)	0.5682 (5)	0.020 (2)	0.134 (3)
O2B	−0.1198 (11)	0.6789 (14)	0.6440 (3)	0.0144 (19)	0.134 (3)
N1B	0.2327 (7)	0.5917 (11)	0.6263 (2)	0.0154 (15)	0.134 (3)
N2B	0.1160 (6)	0.6243 (10)	0.6401 (2)	0.0139 (15)	0.134 (3)
C1	0.22922 (16)	0.4905 (2)	0.58857 (5)	0.0183 (3)
C2	0.14276 (15)	0.4293 (2)	0.55810 (5)	0.0198 (3)
C3	0.19369 (16)	0.3528 (2)	0.52242 (5)	0.0212 (3)
H3	0.1359	0.3117	0.5013	0.025*
C4	0.33026 (16)	0.3377 (2)	0.51824 (5)	0.0196 (3)
H4	0.3657	0.2838	0.4942	0.023*
C5	0.41711 (15)	0.4001 (2)	0.54870 (5)	0.0185 (3)
H5	0.5104	0.3885	0.5452	0.022*
C6	0.36714 (16)	0.4788 (2)	0.58400 (5)	0.0182 (3)
H6	0.4251	0.5237	0.6046	0.022*
C7	0.12395 (17)	0.7392 (2)	0.67434 (5)	0.0201 (3)
C8	−0.01266 (17)	0.7661 (2)	0.66752 (5)	0.0210 (3)
C9	−0.08030 (17)	0.8790 (2)	0.69382 (5)	0.0229 (4)
H9	−0.1723	0.8997	0.6895	0.027*
C10	−0.01415 (17)	0.9606 (2)	0.72602 (5)	0.0205 (3)
H10	−0.0611	1.0366	0.7437	0.025*
C11	0.12105 (16)	0.9317 (2)	0.73271 (5)	0.0215 (3)
H11	0.1659	0.9875	0.7549	0.026*
C12	0.18902 (16)	0.8222 (2)	0.70701 (5)	0.0213 (3)
H12	0.2811	0.8029	0.7115	0.026*
C13	−0.03993 (14)	0.3341 (2)	0.65057 (4)	0.0160 (3)
H13A	−0.0384	0.3831	0.6787	0.024*
H13B	0.0432	0.2730	0.6455	0.024*
H13C	−0.1150	0.2557	0.6482	0.024*
C14	−0.23075 (14)	0.5034 (2)	0.58920 (5)	0.0184 (3)
H14A	−0.2449	0.6047	0.5721	0.028*
H14B	−0.2953	0.5016	0.6121	0.028*
H14C	−0.2423	0.4023	0.5718	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.01105 (19)	0.0152 (2)	0.0160 (2)	−0.00114 (14)	−0.00198 (14)	0.00129 (16)
O1A	0.0107 (7)	0.0233 (12)	0.0175 (7)	−0.0021 (7)	0.0014 (6)	0.0011 (7)
O2A	0.0153 (8)	0.0170 (8)	0.0165 (8)	0.0005 (6)	−0.0024 (6)	−0.0006 (6)
N1A	0.0111 (7)	0.0141 (8)	0.0147 (7)	−0.0017 (5)	−0.0012 (5)	0.0035 (6)
N2A	0.0138 (7)	0.0144 (8)	0.0159 (7)	−0.0021 (5)	−0.0017 (5)	0.0024 (6)
O1B	0.011 (4)	0.019 (5)	0.030 (4)	−0.008 (4)	0.002 (4)	0.010 (4)
O2B	0.019 (4)	0.012 (4)	0.012 (4)	−0.001 (4)	−0.001 (3)	−0.002 (3)
N1B	0.019 (3)	0.015 (3)	0.012 (3)	0.003 (3)	0.004 (3)	0.001 (3)
N2B	0.016 (3)	0.012 (3)	0.013 (3)	0.003 (2)	0.004 (3)	0.001 (2)
C1	0.0257 (8)	0.0142 (8)	0.0151 (6)	0.0040 (6)	0.0048 (6)	0.0038 (6)
C2	0.0133 (7)	0.0253 (9)	0.0209 (7)	0.0018 (6)	0.0036 (6)	0.0092 (7)
C3	0.0174 (7)	0.0292 (9)	0.0169 (7)	−0.0038 (6)	−0.0013 (6)	0.0025 (7)
C4	0.0203 (7)	0.0229 (9)	0.0155 (7)	0.0004 (6)	0.0035 (6)	−0.0010 (6)
C5	0.0142 (6)	0.0198 (8)	0.0214 (7)	0.0004 (6)	0.0007 (6)	0.0034 (6)
C6	0.0230 (8)	0.0150 (8)	0.0167 (7)	−0.0026 (6)	−0.0031 (6)	0.0027 (6)
C7	0.0300 (8)	0.0147 (8)	0.0157 (7)	0.0004 (6)	0.0058 (6)	0.0032 (6)
C8	0.0333 (9)	0.0129 (8)	0.0169 (7)	−0.0017 (6)	−0.0048 (6)	0.0016 (6)
C9	0.0228 (8)	0.0203 (9)	0.0256 (8)	0.0010 (6)	−0.0029 (6)	0.0014 (7)
C10	0.0249 (8)	0.0191 (8)	0.0173 (7)	0.0012 (6)	0.0049 (6)	−0.0021 (6)
C11	0.0235 (8)	0.0215 (9)	0.0194 (7)	−0.0061 (6)	0.0001 (6)	−0.0009 (6)
C12	0.0183 (7)	0.0204 (8)	0.0251 (8)	−0.0029 (6)	0.0050 (6)	0.0040 (7)
C13	0.0135 (6)	0.0179 (8)	0.0166 (7)	−0.0003 (5)	0.0000 (5)	0.0006 (6)
C14	0.0125 (7)	0.0227 (9)	0.0200 (7)	−0.0012 (6)	−0.0017 (5)	0.0007 (6)

Geometric parameters (Å, º)

Si1—O1B	1.617 (12)	C3—H3	0.9500
Si1—O2A	1.6950 (18)	C4—C5	1.399 (2)
Si1—O1A	1.7349 (19)	C4—H4	0.9500
Si1—O2B	1.829 (10)	C5—C6	1.384 (2)
Si1—C13	1.8653 (16)	C5—H5	0.9500
Si1—C14	1.8731 (15)	C6—H6	0.9500
Si1—N1A	2.1750 (15)	C7—C12	1.398 (2)
Si1—N2B	2.191 (5)	C7—C8	1.408 (2)
O1A—C2	1.365 (2)	C8—C9	1.403 (2)
O2A—C8	1.343 (2)	C9—C10	1.386 (2)
N1A—N2A	1.266 (2)	C9—H9	0.9500
N1A—C1	1.405 (2)	C10—C11	1.396 (2)
N2A—C7	1.424 (2)	C10—H10	0.9500
O1B—C2	1.330 (13)	C11—C12	1.376 (2)
O2B—C8	1.485 (10)	C11—H11	0.9500
N1B—N2B	1.281 (5)	C12—H12	0.9500
N1B—C1	1.449 (5)	C13—H13A	0.9800
N2B—C7	1.426 (5)	C13—H13B	0.9800
N2B—C8	1.925 (7)	C13—H13C	0.9800
C1—C2	1.394 (2)	C14—H14A	0.9800
C1—C6	1.399 (2)	C14—H14B	0.9800
C2—C3	1.390 (2)	C14—H14C	0.9800
C3—C4	1.386 (2)
O1B—Si1—O2A	119.0 (5)	C4—C3—C2	118.85 (15)
O2A—Si1—O1A	132.95 (9)	C4—C3—H3	120.6
O1B—Si1—O2B	134.8 (6)	C2—C3—H3	120.6
O1A—Si1—O2B	147.3 (4)	C3—C4—C5	121.46 (15)
O1B—Si1—C13	119.0 (6)	C3—C4—H4	119.3
O2A—Si1—C13	110.80 (8)	C5—C4—H4	119.3
O1A—Si1—C13	110.76 (9)	C6—C5—C4	119.99 (14)
O2B—Si1—C13	101.0 (4)	C6—C5—H5	120.0
O1B—Si1—C14	99.4 (6)	C4—C5—H5	120.0
O2A—Si1—C14	94.50 (8)	C5—C6—C1	118.40 (14)
O1A—Si1—C14	91.59 (9)	C5—C6—H6	120.8
O2B—Si1—C14	84.9 (3)	C1—C6—H6	120.8
C13—Si1—C14	109.64 (7)	C12—C7—C8	120.17 (15)
O1B—Si1—N1A	67.1 (5)	C12—C7—N2A	113.11 (14)
O2A—Si1—N1A	81.75 (7)	C8—C7—N2A	126.29 (15)
O1A—Si1—N1A	77.98 (8)	C12—C7—N2B	154.3 (3)
O2B—Si1—N1A	95.4 (3)	C8—C7—N2B	85.5 (3)
C13—Si1—N1A	88.86 (6)	O2A—C8—C9	119.49 (16)
C14—Si1—N1A	161.15 (7)	O2A—C8—C7	121.85 (16)
O1B—Si1—N2B	87.9 (6)	C9—C8—C7	118.48 (15)
O2A—Si1—N2B	61.4 (2)	C9—C8—O2B	104.3 (4)
O1A—Si1—N2B	100.11 (18)	C7—C8—O2B	135.9 (4)
O2B—Si1—N2B	73.2 (4)	O2A—C8—N2B	74.41 (18)
C13—Si1—N2B	86.9 (3)	C9—C8—N2B	166.1 (2)
C14—Si1—N2B	155.0 (2)	C7—C8—N2B	47.61 (16)
C2—O1A—Si1	121.59 (16)	O2B—C8—N2B	89.3 (4)
C8—O2A—Si1	131.20 (14)	C10—C9—C8	120.59 (15)
N2A—N1A—C1	116.60 (14)	C10—C9—H9	119.7
N2A—N1A—Si1	132.07 (12)	C8—C9—H9	119.7
C1—N1A—Si1	111.22 (11)	C9—C10—C11	120.41 (15)
N1A—N2A—C7	112.25 (14)	C9—C10—H10	119.8
C2—O1B—Si1	133.6 (12)	C11—C10—H10	119.8
C8—O2B—Si1	113.0 (6)	C12—C11—C10	119.71 (15)
N2B—N1B—C1	112.1 (5)	C12—C11—H11	120.1
N1B—N2B—C7	109.9 (4)	C10—C11—H11	120.1
N1B—N2B—C8	153.0 (5)	C11—C12—C7	120.63 (15)
C7—N2B—C8	46.8 (2)	C11—C12—H12	119.7
N1B—N2B—Si1	120.2 (4)	C7—C12—H12	119.7
C7—N2B—Si1	129.8 (4)	Si1—C13—H13A	109.5
C8—N2B—Si1	84.4 (2)	Si1—C13—H13B	109.5
C2—C1—C6	121.57 (14)	H13A—C13—H13B	109.5
C2—C1—N1A	107.05 (14)	Si1—C13—H13C	109.5
C6—C1—N1A	131.27 (15)	H13A—C13—H13C	109.5
C2—C1—N1B	142.2 (3)	H13B—C13—H13C	109.5
C6—C1—N1B	95.7 (3)	Si1—C14—H14A	109.5
O1B—C2—C3	134.3 (7)	Si1—C14—H14B	109.5
O1A—C2—C3	120.75 (16)	H14A—C14—H14B	109.5
O1B—C2—C1	104.2 (7)	Si1—C14—H14C	109.5
O1A—C2—C1	119.55 (16)	H14A—C14—H14C	109.5
C3—C2—C1	119.70 (14)	H14B—C14—H14C	109.5
O1B—Si1—O1A—C2	56 (2)	N2B—N1B—C1—N1A	−1.9 (5)
O2A—Si1—O1A—C2	80.4 (2)	Si1—O1B—C2—O1A	95 (3)
O2B—Si1—O1A—C2	94.9 (6)	Si1—O1B—C2—C3	146.6 (9)
C13—Si1—O1A—C2	−70.26 (19)	Si1—O1B—C2—C1	−49.4 (13)
C14—Si1—O1A—C2	178.02 (18)	Si1—O1A—C2—O1B	−52 (2)
N1A—Si1—O1A—C2	13.85 (17)	Si1—O1A—C2—C3	168.53 (15)
N2B—Si1—O1A—C2	20.3 (3)	Si1—O1A—C2—C1	−11.9 (3)
O1B—Si1—O2A—C8	−99.6 (7)	C6—C1—C2—O1B	−166.1 (7)
O1A—Si1—O2A—C8	−106.6 (2)	N1A—C1—C2—O1B	10.6 (7)
O2B—Si1—O2A—C8	101.0 (14)	N1B—C1—C2—O1B	3.1 (10)
C13—Si1—O2A—C8	44.0 (2)	C6—C1—C2—O1A	−178.82 (17)
C14—Si1—O2A—C8	156.99 (18)	N1A—C1—C2—O1A	−2.1 (2)
N1A—Si1—O2A—C8	−41.60 (18)	N1B—C1—C2—O1A	−9.6 (7)
N2B—Si1—O2A—C8	−30.2 (3)	C6—C1—C2—C3	0.7 (2)
O1B—Si1—N1A—N2A	158.9 (6)	N1A—C1—C2—C3	177.44 (15)
O2A—Si1—N1A—N2A	32.46 (16)	N1B—C1—C2—C3	169.9 (6)
O1A—Si1—N1A—N2A	169.74 (18)	O1B—C2—C3—C4	162.7 (9)
O2B—Si1—N1A—N2A	22.1 (4)	O1A—C2—C3—C4	−179.77 (18)
C13—Si1—N1A—N2A	−78.75 (16)	C1—C2—C3—C4	0.7 (2)
C14—Si1—N1A—N2A	112.1 (2)	C2—C3—C4—C5	−1.1 (3)
N2B—Si1—N1A—N2A	6.0 (6)	C3—C4—C5—C6	0.1 (3)
O1B—Si1—N1A—C1	−25.2 (6)	C4—C5—C6—C1	1.3 (2)
O2A—Si1—N1A—C1	−151.62 (12)	C2—C1—C6—C5	−1.7 (2)
O1A—Si1—N1A—C1	−14.34 (13)	N1A—C1—C6—C5	−177.54 (16)
O2B—Si1—N1A—C1	−161.9 (4)	N1B—C1—C6—C5	−175.1 (4)
C13—Si1—N1A—C1	97.17 (11)	N1A—N2A—C7—C12	176.69 (14)
C14—Si1—N1A—C1	−72.0 (3)	N1A—N2A—C7—C8	−10.9 (2)
N2B—Si1—N1A—C1	−178.0 (7)	N1A—N2A—C7—N2B	3.5 (6)
C1—N1A—N2A—C7	171.94 (14)	N1B—N2B—C7—C12	−19.4 (15)
Si1—N1A—N2A—C7	−12.3 (2)	C8—N2B—C7—C12	177.0 (8)
O2A—Si1—O1B—C2	110.6 (12)	Si1—N2B—C7—C12	160.2 (3)
O1A—Si1—O1B—C2	−90 (3)	N1B—N2B—C7—C8	163.6 (8)
O2B—Si1—O1B—C2	118.9 (13)	Si1—N2B—C7—C8	−16.8 (6)
C13—Si1—O1B—C2	−30.0 (15)	N1B—N2B—C7—N2A	−4.8 (5)
C14—Si1—O1B—C2	−148.9 (12)	C8—N2B—C7—N2A	−168.4 (5)
N1A—Si1—O1B—C2	44.9 (11)	Si1—N2B—C7—N2A	174.9 (11)
N2B—Si1—O1B—C2	55.2 (13)	Si1—O2A—C8—C9	−149.21 (16)
O1B—Si1—O2B—C8	−72.2 (12)	Si1—O2A—C8—C7	35.7 (3)
O2A—Si1—O2B—C8	−46.5 (9)	Si1—O2A—C8—O2B	−101.6 (14)
O1A—Si1—O2B—C8	−85.4 (9)	Si1—O2A—C8—N2B	31.4 (3)
C13—Si1—O2B—C8	80.5 (7)	C12—C7—C8—O2A	175.96 (16)
C14—Si1—O2B—C8	−170.4 (7)	N2A—C7—C8—O2A	4.1 (3)
N1A—Si1—O2B—C8	−9.4 (7)	N2B—C7—C8—O2A	−5.5 (4)
N2B—Si1—O2B—C8	−2.9 (6)	C12—C7—C8—C9	0.8 (2)
C1—N1B—N2B—C7	−173.5 (6)	N2A—C7—C8—C9	−171.10 (16)
C1—N1B—N2B—C8	−146.5 (12)	N2B—C7—C8—C9	179.3 (4)
C1—N1B—N2B—Si1	6.8 (11)	C12—C7—C8—O2B	−163.4 (7)
O1B—Si1—N2B—N1B	−27.8 (10)	N2A—C7—C8—O2B	24.7 (7)
O2A—Si1—N2B—N1B	−152.8 (9)	N2B—C7—C8—O2B	15.1 (8)
O1A—Si1—N2B—N1B	−19.1 (9)	C12—C7—C8—N2B	−178.5 (4)
O2B—Si1—N2B—N1B	−166.2 (10)	N2A—C7—C8—N2B	9.6 (4)
C13—Si1—N2B—N1B	91.4 (8)	Si1—O2B—C8—O2A	47.9 (9)
C14—Si1—N2B—N1B	−135.7 (6)	Si1—O2B—C8—C9	−173.7 (5)
N1A—Si1—N2B—N1B	−2.9 (5)	Si1—O2B—C8—C7	−8.0 (11)
O1B—Si1—N2B—C7	152.6 (9)	Si1—O2B—C8—N2B	3.1 (7)
O2A—Si1—N2B—C7	27.6 (6)	N1B—N2B—C8—O2A	139.3 (17)
O1A—Si1—N2B—C7	161.3 (7)	C7—N2B—C8—O2A	175.1 (4)
O2B—Si1—N2B—C7	14.3 (7)	Si1—N2B—C8—O2A	−17.76 (17)
C13—Si1—N2B—C7	−88.1 (7)	N1B—N2B—C8—C9	−38 (3)
C14—Si1—N2B—C7	44.7 (11)	C7—N2B—C8—C9	−2.5 (15)
N1A—Si1—N2B—C7	177.5 (13)	Si1—N2B—C8—C9	164.6 (11)
O1B—Si1—N2B—C8	140.4 (6)	N1B—N2B—C8—C7	−35.8 (14)
O2A—Si1—N2B—C8	15.38 (16)	Si1—N2B—C8—C7	167.1 (5)
O1A—Si1—N2B—C8	149.1 (2)	N1B—N2B—C8—O2B	154.7 (17)
O2B—Si1—N2B—C8	2.0 (4)	C7—N2B—C8—O2B	−169.5 (6)
C13—Si1—N2B—C8	−100.4 (3)	Si1—N2B—C8—O2B	−2.4 (5)
C14—Si1—N2B—C8	32.5 (7)	O2A—C8—C9—C10	−175.94 (16)
N1A—Si1—N2B—C8	165.3 (9)	C7—C8—C9—C10	−0.7 (2)
N2A—N1A—C1—C2	−171.89 (14)	O2B—C8—C9—C10	168.0 (5)
Si1—N1A—C1—C2	11.50 (15)	N2B—C8—C9—C10	1.5 (13)
N2A—N1A—C1—C6	4.4 (3)	C8—C9—C10—C11	0.1 (3)
Si1—N1A—C1—C6	−172.24 (15)	C9—C10—C11—C12	0.3 (3)
N2A—N1A—C1—N1B	0.2 (7)	C10—C11—C12—C7	−0.2 (2)
Si1—N1A—C1—N1B	−176.4 (7)	C8—C7—C12—C11	−0.4 (2)
N2B—N1B—C1—C2	10.5 (12)	N2A—C7—C12—C11	172.52 (15)
N2B—N1B—C1—C6	−178.8 (8)	N2B—C7—C12—C11	−176.9 (9)

(II_93K_slow_cooled) (2,2'-diazenediyldiphenolato-κ³O,N,O')dimethylsilicon

Crystal data

C14H14N2O2Si	Dx = 1.412 Mg m^−3
Mr = 270.36	Melting point: 388 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6404 reflections
a = 10.0248 (10) Å	θ = 2.4–36.2°
b = 7.8879 (8) Å	µ = 0.18 mm^−1
c = 32.162 (3) Å	T = 93 K
V = 2543.2 (4) Å^3	Prism, red
Z = 8	0.45 × 0.18 × 0.15 mm
F(000) = 1136

Data collection

Bruker SMART CCD area-detector diffractometer	2341 independent reflections
Radiation source: sealed tube	2116 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
phi and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.921, Tmax = 0.978	k = −9→9
11554 measured reflections	l = −25→39

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0388P)^2 + 1.7649P] where P = (Fo^2 + 2Fc^2)/3
2341 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.38 e Å^−3
64 restraints	Δρmin = −0.29 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.

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	Occ. (<1)
Si1	−0.05790 (4)	0.51192 (5)	0.610646 (12)	0.01307 (13)
O1A	0.00827 (11)	0.45205 (19)	0.56343 (3)	0.0171 (4)	0.959 (2)
O2A	−0.07556 (12)	0.70328 (16)	0.63493 (4)	0.0168 (4)	0.959 (2)
N1A	0.15191 (12)	0.56873 (18)	0.61939 (4)	0.0137 (3)	0.959 (2)
N2A	0.21377 (12)	0.64832 (18)	0.64778 (4)	0.0147 (3)	0.959 (2)
O1B	0.022 (2)	0.508 (5)	0.5635 (3)	0.019 (3)	0.041 (2)
O2B	−0.0929 (9)	0.677 (4)	0.6439 (10)	0.018 (3)	0.041 (2)
N1B	0.2247 (12)	0.589 (3)	0.6250 (6)	0.0144 (18)	0.041 (2)
N2B	0.1128 (9)	0.629 (3)	0.6410 (6)	0.0137 (18)	0.041 (2)
C1	0.22742 (15)	0.4920 (2)	0.58806 (4)	0.0154 (3)
C2	0.14120 (14)	0.4314 (2)	0.55746 (5)	0.0161 (3)
C3	0.19253 (15)	0.3552 (2)	0.52181 (5)	0.0190 (4)
H3	0.1348	0.3142	0.5007	0.023*
C4	0.32989 (15)	0.3405 (2)	0.51788 (5)	0.0185 (3)
H4	0.3661	0.2874	0.4939	0.022*
C5	0.41641 (14)	0.4024 (2)	0.54858 (5)	0.0172 (3)
H5	0.5101	0.3908	0.5452	0.021*
C6	0.36613 (15)	0.4803 (2)	0.58373 (5)	0.0159 (3)
H6	0.4241	0.5247	0.6044	0.019*
C7	0.12905 (14)	0.7402 (2)	0.67459 (4)	0.0160 (3)
C8	−0.00802 (15)	0.7704 (2)	0.66733 (4)	0.0165 (3)
C9	−0.07507 (15)	0.8833 (2)	0.69342 (5)	0.0199 (4)
H9	−0.1667	0.9070	0.6886	0.024*
C10	−0.01013 (16)	0.9616 (2)	0.72628 (5)	0.0190 (3)
H10	−0.0576	1.0375	0.7438	0.023*
C11	0.12494 (16)	0.9292 (2)	0.73374 (5)	0.0194 (3)
H11	0.1692	0.9819	0.7565	0.023*
C12	0.19313 (15)	0.8206 (2)	0.70791 (5)	0.0181 (3)
H12	0.2852	0.7998	0.7127	0.022*
C13	−0.04153 (14)	0.3399 (2)	0.65008 (4)	0.0160 (3)
H13A	−0.0362	0.3899	0.6779	0.024*
H13B	0.0396	0.2743	0.6445	0.024*
H13C	−0.1194	0.2650	0.6485	0.024*
C14	−0.23225 (14)	0.5138 (2)	0.58948 (5)	0.0171 (3)
H14A	−0.2461	0.6171	0.5731	0.026*
H14B	−0.2961	0.5110	0.6126	0.026*
H14C	−0.2457	0.4143	0.5717	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0110 (2)	0.0146 (3)	0.0136 (2)	−0.00068 (14)	−0.00094 (15)	0.00052 (16)
O1A	0.0119 (5)	0.0231 (9)	0.0164 (6)	−0.0012 (5)	0.0009 (4)	0.0012 (5)
O2A	0.0184 (5)	0.0161 (7)	0.0159 (7)	0.0013 (5)	−0.0041 (4)	−0.0005 (6)
N1A	0.0137 (6)	0.0135 (8)	0.0140 (6)	−0.0014 (5)	−0.0011 (5)	0.0035 (5)
N2A	0.0162 (6)	0.0139 (8)	0.0140 (6)	−0.0019 (5)	−0.0014 (5)	0.0023 (5)
O1B	0.012 (5)	0.022 (5)	0.023 (5)	−0.002 (5)	0.003 (5)	0.006 (5)
O2B	0.027 (5)	0.013 (5)	0.014 (5)	0.001 (5)	−0.009 (5)	0.002 (5)
N1B	0.017 (3)	0.013 (3)	0.013 (3)	−0.001 (3)	0.000 (3)	0.003 (3)
N2B	0.015 (3)	0.013 (3)	0.013 (3)	−0.002 (3)	−0.001 (3)	0.002 (3)
C1	0.0208 (8)	0.0127 (9)	0.0128 (7)	0.0021 (6)	0.0030 (6)	0.0037 (6)
C2	0.0134 (7)	0.0178 (9)	0.0170 (7)	0.0005 (6)	0.0014 (6)	0.0059 (6)
C3	0.0194 (7)	0.0231 (10)	0.0147 (7)	−0.0026 (6)	−0.0014 (6)	0.0007 (6)
C4	0.0203 (7)	0.0206 (10)	0.0147 (7)	0.0014 (6)	0.0039 (6)	−0.0005 (6)
C5	0.0141 (7)	0.0189 (9)	0.0187 (7)	0.0018 (6)	0.0016 (6)	0.0033 (6)
C6	0.0189 (7)	0.0135 (9)	0.0152 (7)	−0.0013 (6)	−0.0022 (6)	0.0026 (6)
C7	0.0211 (7)	0.0133 (9)	0.0136 (7)	−0.0007 (6)	0.0038 (6)	0.0027 (6)
C8	0.0232 (8)	0.0125 (9)	0.0140 (7)	−0.0024 (6)	−0.0016 (6)	0.0012 (6)
C9	0.0192 (7)	0.0201 (10)	0.0205 (8)	0.0016 (6)	−0.0005 (6)	0.0016 (7)
C10	0.0235 (8)	0.0175 (9)	0.0160 (7)	0.0007 (6)	0.0054 (6)	−0.0012 (6)
C11	0.0228 (8)	0.0203 (10)	0.0152 (7)	−0.0050 (6)	0.0000 (6)	−0.0012 (6)
C12	0.0163 (7)	0.0188 (9)	0.0190 (7)	−0.0027 (6)	0.0013 (6)	0.0035 (6)
C13	0.0145 (7)	0.0181 (9)	0.0154 (7)	−0.0005 (6)	0.0004 (5)	0.0010 (6)
C14	0.0132 (7)	0.0198 (9)	0.0183 (7)	−0.0006 (6)	−0.0007 (6)	−0.0001 (6)

Geometric parameters (Å, º)

Si1—O2A	1.7087 (12)	C3—H3	0.9500
Si1—O1B	1.715 (4)	C4—C5	1.402 (2)
Si1—O2B	1.718 (5)	C4—H4	0.9500
Si1—O1A	1.7231 (11)	C5—C6	1.381 (2)
Si1—C13	1.8647 (16)	C5—H5	0.9500
Si1—C14	1.8757 (15)	C6—H6	0.9500
Si1—N1A	2.1688 (14)	C7—C12	1.401 (2)
Si1—N2B	2.174 (5)	C7—C8	1.414 (2)
O1A—C2	1.3561 (17)	C8—C9	1.396 (2)
O2A—C8	1.3508 (17)	C9—C10	1.386 (2)
N1A—N2A	1.2698 (18)	C9—H9	0.9500
N1A—C1	1.3982 (19)	C10—C11	1.399 (2)
N2A—C7	1.4107 (19)	C10—H10	0.9500
O1B—C2	1.354 (5)	C11—C12	1.375 (2)
O2B—C8	1.356 (5)	C11—H11	0.9500
N1B—N2B	1.272 (5)	C12—H12	0.9500
N1B—C1	1.415 (5)	C13—H13A	0.9800
N2B—C7	1.403 (5)	C13—H13B	0.9800
N2B—C8	1.853 (12)	C13—H13C	0.9800
C1—C2	1.394 (2)	C14—H14A	0.9800
C1—C6	1.401 (2)	C14—H14B	0.9800
C2—C3	1.393 (2)	C14—H14C	0.9800
C3—C4	1.388 (2)
O2A—Si1—O1B	118.1 (13)	C4—C3—C2	118.53 (14)
O1B—Si1—O2B	131.4 (19)	C4—C3—H3	120.7
O2A—Si1—O1A	133.22 (7)	C2—C3—H3	120.7
O2B—Si1—O1A	146.5 (14)	C3—C4—C5	121.37 (14)
O2A—Si1—C13	109.95 (7)	C3—C4—H4	119.3
O1B—Si1—C13	123.1 (7)	C5—C4—H4	119.3
O2B—Si1—C13	98.3 (15)	C6—C5—C4	120.35 (13)
O1A—Si1—C13	111.47 (7)	C6—C5—H5	119.8
O2A—Si1—C14	93.58 (7)	C4—C5—H5	119.8
O1B—Si1—C14	96.5 (7)	C5—C6—C1	118.23 (14)
O2B—Si1—C14	91.7 (4)	C5—C6—H6	120.9
O1A—Si1—C14	92.35 (6)	C1—C6—H6	120.9
C13—Si1—C14	109.54 (7)	C12—C7—N2B	157.9 (6)
O2A—Si1—N1A	81.87 (6)	C12—C7—N2A	115.09 (13)
O1B—Si1—N1A	70.6 (10)	C12—C7—C8	119.71 (14)
O2B—Si1—N1A	87.8 (3)	N2B—C7—C8	82.3 (5)
O1A—Si1—N1A	78.32 (5)	N2A—C7—C8	124.79 (13)
C13—Si1—N1A	88.67 (6)	O2A—C8—C9	118.19 (13)
C14—Si1—N1A	161.64 (7)	O2B—C8—C9	112.4 (4)
O2A—Si1—N2B	60.1 (5)	O2A—C8—C7	123.27 (14)
O1B—Si1—N2B	92.3 (13)	O2B—C8—C7	127.5 (4)
O2B—Si1—N2B	64.0 (4)	C9—C8—C7	118.42 (14)
O1A—Si1—N2B	102.0 (3)	O2A—C8—N2B	74.8 (3)
C13—Si1—N2B	86.2 (8)	O2B—C8—N2B	80.0 (3)
C14—Si1—N2B	153.2 (6)	C9—C8—N2B	167.0 (3)
C2—O1A—Si1	122.41 (10)	C7—C8—N2B	48.6 (2)
C8—O2A—Si1	130.30 (11)	C10—C9—C8	121.07 (14)
N2A—N1A—C1	117.90 (13)	C10—C9—H9	119.5
N2A—N1A—Si1	131.99 (10)	C8—C9—H9	119.5
C1—N1A—Si1	110.01 (10)	C9—C10—C11	120.30 (15)
N1A—N2A—C7	113.55 (12)	C9—C10—H10	119.9
C2—O1B—Si1	123.1 (4)	C11—C10—H10	119.9
C8—O2B—Si1	129.1 (5)	C12—C11—C10	119.41 (15)
N2B—N1B—C1	119.3 (9)	C12—C11—H11	120.3
N1B—N2B—C7	111.2 (4)	C10—C11—H11	120.3
N1B—N2B—C8	155.3 (16)	C11—C12—C7	121.07 (14)
C7—N2B—C8	49.1 (3)	C11—C12—H12	119.5
N1B—N2B—Si1	114.1 (6)	C7—C12—H12	119.5
C7—N2B—Si1	134.7 (6)	Si1—C13—H13A	109.5
C8—N2B—Si1	86.9 (4)	Si1—C13—H13B	109.5
C2—C1—N1A	108.74 (13)	H13A—C13—H13B	109.5
C2—C1—C6	121.51 (14)	Si1—C13—H13C	109.5
N1A—C1—C6	129.63 (14)	H13A—C13—H13C	109.5
C2—C1—N1B	140.1 (5)	H13B—C13—H13C	109.5
C6—C1—N1B	98.0 (5)	Si1—C14—H14A	109.5
O1B—C2—C3	129.5 (9)	Si1—C14—H14B	109.5
O1A—C2—C3	122.09 (13)	H14A—C14—H14B	109.5
O1B—C2—C1	107.2 (14)	Si1—C14—H14C	109.5
O1A—C2—C1	117.92 (13)	H14A—C14—H14C	109.5
C3—C2—C1	119.98 (13)	H14B—C14—H14C	109.5
O2A—Si1—O1A—C2	81.15 (16)	N2B—N1B—C1—C6	−179 (3)
O1B—Si1—O1A—C2	72.2 (16)	Si1—O1B—C2—O1A	75.6 (17)
O2B—Si1—O1A—C2	81.6 (9)	Si1—O1B—C2—C3	150.3 (16)
C13—Si1—O1A—C2	−69.62 (15)	Si1—O1B—C2—C1	−51 (3)
C14—Si1—O1A—C2	178.30 (14)	Si1—O1A—C2—O1B	−72.9 (15)
N1A—Si1—O1A—C2	14.25 (13)	Si1—O1A—C2—C3	168.57 (13)
N2B—Si1—O1A—C2	21.0 (8)	Si1—O1A—C2—C1	−12.5 (2)
O1B—Si1—O2A—C8	−103.1 (7)	N1A—C1—C2—O1B	16.1 (12)
O2B—Si1—O2A—C8	75 (2)	C6—C1—C2—O1B	−160.4 (12)
O1A—Si1—O2A—C8	−105.81 (15)	N1B—C1—C2—O1B	10 (2)
C13—Si1—O2A—C8	45.28 (16)	N1A—C1—C2—O1A	−1.6 (2)
C14—Si1—O2A—C8	157.57 (15)	C6—C1—C2—O1A	−178.07 (14)
N1A—Si1—O2A—C8	−40.32 (14)	N1B—C1—C2—O1A	−8 (2)
N2B—Si1—O2A—C8	−27.9 (8)	N1A—C1—C2—C3	177.37 (14)
O2A—Si1—N1A—N2A	32.55 (15)	C6—C1—C2—C3	0.9 (2)
O1B—Si1—N1A—N2A	156.2 (11)	N1B—C1—C2—C3	171 (2)
O2B—Si1—N1A—N2A	20.6 (15)	O1B—C2—C3—C4	157 (2)
O1A—Si1—N1A—N2A	169.93 (15)	O1A—C2—C3—C4	179.34 (15)
C13—Si1—N1A—N2A	−77.82 (15)	C1—C2—C3—C4	0.4 (2)
C14—Si1—N1A—N2A	109.3 (2)	C2—C3—C4—C5	−0.8 (2)
N2B—Si1—N1A—N2A	6 (2)	C3—C4—C5—C6	−0.1 (2)
O2A—Si1—N1A—C1	−151.36 (11)	C4—C5—C6—C1	1.3 (2)
O1B—Si1—N1A—C1	−27.7 (11)	C2—C1—C6—C5	−1.7 (2)
O2B—Si1—N1A—C1	−163.3 (15)	N1A—C1—C6—C5	−177.45 (15)
O1A—Si1—N1A—C1	−13.98 (10)	N1B—C1—C6—C5	−175.4 (13)
C13—Si1—N1A—C1	98.27 (11)	N1B—N2B—C7—C12	−24 (5)
C14—Si1—N1A—C1	−74.7 (2)	C8—N2B—C7—C12	173 (3)
N2B—Si1—N1A—C1	−178 (2)	Si1—N2B—C7—C12	155.9 (6)
C1—N1A—N2A—C7	171.85 (13)	N1B—N2B—C7—N2A	−5.0 (17)
Si1—N1A—N2A—C7	−12.3 (2)	C8—N2B—C7—N2A	−167.3 (15)
O2A—Si1—O1B—C2	113 (3)	Si1—N2B—C7—N2A	175 (4)
O2B—Si1—O1B—C2	113 (3)	N1B—N2B—C7—C8	162 (3)
O1A—Si1—O1B—C2	−74.1 (18)	Si1—N2B—C7—C8	−17 (2)
C13—Si1—O1B—C2	−31 (4)	N1A—N2A—C7—C12	176.02 (13)
C14—Si1—O1B—C2	−149 (3)	N1A—N2A—C7—N2B	4.0 (18)
N1A—Si1—O1B—C2	44 (3)	N1A—N2A—C7—C8	−11.4 (2)
N2B—Si1—O1B—C2	56 (3)	Si1—O2A—C8—O2B	−76 (2)
O2A—Si1—O2B—C8	−71.1 (18)	Si1—O2A—C8—C9	−150.09 (13)
O1B—Si1—O2B—C8	−69 (4)	Si1—O2A—C8—C7	34.0 (2)
O1A—Si1—O2B—C8	−73 (4)	Si1—O2A—C8—N2B	29.6 (9)
C13—Si1—O2B—C8	80 (4)	Si1—O2B—C8—O2A	71.7 (17)
C14—Si1—O2B—C8	−170 (4)	Si1—O2B—C8—C9	−174 (3)
N1A—Si1—O2B—C8	−8 (4)	Si1—O2B—C8—C7	−10 (5)
N2B—Si1—O2B—C8	−1 (3)	Si1—O2B—C8—N2B	1 (3)
C1—N1B—N2B—C7	−173 (2)	C12—C7—C8—O2A	177.20 (15)
C1—N1B—N2B—C8	−140 (4)	N2B—C7—C8—O2A	−5.7 (12)
C1—N1B—N2B—Si1	6 (4)	N2A—C7—C8—O2A	4.9 (3)
O2A—Si1—N2B—N1B	−152 (3)	C12—C7—C8—O2B	−163 (2)
O1B—Si1—N2B—N1B	−30 (3)	N2B—C7—C8—O2B	14 (3)
O2B—Si1—N2B—N1B	−166 (3)	N2A—C7—C8—O2B	25 (2)
O1A—Si1—N2B—N1B	−18 (3)	C12—C7—C8—C9	1.3 (2)
C13—Si1—N2B—N1B	93 (2)	N2B—C7—C8—C9	178.4 (12)
C14—Si1—N2B—N1B	−139.4 (18)	N2A—C7—C8—C9	−171.00 (15)
N1A—Si1—N2B—N1B	−2.2 (16)	C12—C7—C8—N2B	−177.1 (12)
O2A—Si1—N2B—C7	28 (2)	N2A—C7—C8—N2B	10.6 (12)
O1B—Si1—N2B—C7	149 (3)	N1B—N2B—C8—O2A	132 (6)
O2B—Si1—N2B—C7	14 (3)	C7—N2B—C8—O2A	175.1 (11)
O1A—Si1—N2B—C7	161 (2)	Si1—N2B—C8—O2A	−17.2 (5)
C13—Si1—N2B—C7	−87 (3)	N1B—N2B—C8—O2B	149 (6)
C14—Si1—N2B—C7	40 (4)	C7—N2B—C8—O2B	−168 (2)
N1A—Si1—N2B—C7	177 (4)	Si1—N2B—C8—O2B	−1 (2)
O2A—Si1—N2B—C8	15.1 (5)	N1B—N2B—C8—C9	−49 (9)
O1B—Si1—N2B—C8	136.4 (12)	C7—N2B—C8—C9	−6 (5)
O2B—Si1—N2B—C8	0.7 (17)	Si1—N2B—C8—C9	161 (3)
O1A—Si1—N2B—C8	148.3 (7)	N1B—N2B—C8—C7	−43 (5)
C13—Si1—N2B—C8	−100.5 (9)	Si1—N2B—C8—C7	167.7 (16)
C14—Si1—N2B—C8	27 (2)	O2A—C8—C9—C10	−177.54 (15)
N1A—Si1—N2B—C8	164 (3)	O2B—C8—C9—C10	165 (2)
N2A—N1A—C1—C2	−172.29 (13)	C7—C8—C9—C10	−1.4 (2)
Si1—N1A—C1—C2	10.99 (15)	N2B—C8—C9—C10	4 (4)
N2A—N1A—C1—C6	3.8 (2)	C8—C9—C10—C11	0.4 (2)
Si1—N1A—C1—C6	−172.88 (14)	C9—C10—C11—C12	0.7 (2)
N2A—N1A—C1—N1B	0 (3)	C10—C11—C12—C7	−0.8 (2)
Si1—N1A—C1—N1B	−177 (3)	N2B—C7—C12—C11	−172 (3)
N2B—N1B—C1—C2	9 (4)	N2A—C7—C12—C11	172.84 (14)
N2B—N1B—C1—N1A	−2.1 (16)	C8—C7—C12—C11	−0.2 (2)