Benzyl 2-{(tert-butyl­dimethyl­silyl­oxy)[1-(4-nitro­phen­yl)-2,5-dioxotetra­hydro-1H-furo[3,2-d]oxazol-6a-yl]meth­yl}­acrylate

The title compound, C₂₈H₃₂N₂O₉Si, contains a rigid [3,3]-bicyclic oxazoledione core. The substituent on the quaternary bridge C atom contains two long-chain hydro­phobic groups that are in extended conformations.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.049
• wR factor = 0.056
• Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level B
            Crystal system given = triclinic
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.16 Ratio
PLAT220_ALERT_2_B Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.55 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.89 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C25

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.5946
            Proportion of unique data used    0.6306
            Ratio reflections to parameters   9.3152
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.32
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         Si
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT432_ALERT_2_C Short Inter X...Y Contact  O4     ..  C5      ..       2.95 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C5     ..  C5      ..       3.12 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         32

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C1     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C4     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C12    = ...          S

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

We have reported a facile synthesis of alpha-substituted gamma- hydroxybutenolides (Patil & Liu, 2007). In an effort to trap the epimerizable gamma-hydroxy group of butenolide, (I), using an isocyanate, (II), we report the synthesis and structure of the title compound, (III). This molecule contains a substituted dihydro-1H-furo[3,2-d]oxazole-2,5-dione ring, which is a new bicyclic oxazole-dione ring.

Related literature

For background literature, see Patil & Liu (2007).

S2. Experimental

To a stirred solution of TBS-protected butenolide, (I) (48.7 mg, 0.12 mmol), in ethyl acetate (0.1 ml) was added 4-nitrophenyl isocyanate (23.9 mg, 0.13 mmol) under nitrogen. The reaction mixture was refluxed for 4 h, cooled to room temperature, stirred for 5 min and filtered. The yellow solid obtained was recrystallized from analytical grade methanol, resulting in colourless blocks of (III) after two weeks at room temperature.

S3. Refinement

The hydrogen atoms were included in positions calculated each cycle (C—H = 1.00 Å) with U_iso(H) = U_eq(carrier).

Computing details

Data collection: CAD-4 Software (Schagen et al., 1989); cell refinement: CAD-4 Software; data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: RAELS (Rae, 1996); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: local programs.

Figures

	Fig. 1. View of the molecular structure of (III) with ellipsoids at the 10% probability level. H atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Reaction scheme for the synthesis of the title compound.

Benzyl 2-{(tert-butyldimethylsilyloxy)[1-(4-nitrophenyl)-2,5-dioxo- tetrahydro-1H-furo[3,2-d]oxazol-6a-yl]methyl}acrylate

Crystal data

C28H32N2O9Si	Z = 2
Mr = 568.7	F(000) = 600.0
Triclinic, P1	Dx = 1.28 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.680 (3) Å	Cell parameters from 11 reflections
b = 11.674 (5) Å	θ = 10–11°
c = 13.565 (6) Å	µ = 0.13 mm^−1
α = 88.75 (3)°	T = 294 K
β = 79.74 (2)°	Block, colourless
γ = 77.13 (3)°	0.25 × 0.20 × 0.18 mm
V = 1470.2 (9) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	θmax = 25°
ω–2θ scans	h = −11→11
5435 measured reflections	k = 0→13
5155 independent reflections	l = −16→16
3251 reflections with I > 2σ(I)	1 standard reflections every 30 min
Rint = 0.014	intensity decay: none

Refinement

Refinement on F	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(F) + 0.0004F^2]
wR(F^2) = 0.056	(Δ/σ)max = 0.004
S = 1.63	Δρmax = 0.35 e Å^−3
3251 reflections	Δρmin = −0.31 e Å^−3
349 parameters

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

	x	y	z	Uiso*/Ueq
Si	−0.08195 (9)	0.80484 (8)	0.28619 (7)	0.0587 (2)
O1	0.0289 (3)	0.6174 (2)	0.6306 (2)	0.0848 (6)
O2	0.1842 (2)	0.7201 (2)	0.5547 (2)	0.0633 (5)
O3	0.4176 (2)	0.6957 (2)	0.4719 (2)	0.0610 (5)
O4	0.6132 (2)	0.5552 (2)	0.4210 (2)	0.0676 (5)
O5	0.4899 (4)	0.0689 (3)	0.1494 (3)	0.1317 (9)
O6	0.6812 (4)	0.1245 (3)	0.0786 (3)	0.175 (1)
O7	0.3549 (2)	0.5878 (2)	0.1139 (2)	0.0739 (5)
O8	0.5189 (2)	0.6936 (2)	0.1211 (1)	0.0619 (5)
O9	0.0631 (2)	0.7679 (2)	0.3410 (1)	0.0492 (4)
N1	0.3987 (2)	0.5594 (2)	0.3654 (2)	0.0450 (5)
N2	0.5680 (5)	0.1378 (3)	0.1371 (3)	0.1077 (9)
C1	0.2516 (3)	0.6296 (2)	0.3915 (2)	0.0407 (5)
C2	0.1478 (3)	0.5681 (3)	0.4599 (2)	0.0456 (6)
C3	0.1107 (3)	0.6329 (3)	0.5571 (2)	0.0568 (7)
C4	0.2720 (3)	0.7247 (3)	0.4602 (2)	0.0518 (6)
C5	0.4890 (3)	0.5969 (3)	0.4187 (2)	0.0531 (6)
C6	0.4399 (3)	0.4533 (2)	0.3081 (2)	0.0459 (6)
C7	0.5839 (3)	0.4126 (3)	0.2643 (3)	0.0688 (8)
C8	0.6237 (4)	0.3104 (3)	0.2080 (3)	0.0861 (9)
C9	0.5229 (4)	0.2480 (3)	0.1969 (3)	0.0721 (8)
C10	0.3809 (4)	0.2869 (3)	0.2384 (2)	0.0617 (7)
C11	0.3395 (3)	0.3907 (3)	0.2929 (2)	0.0522 (6)
C12	0.1906 (3)	0.6864 (2)	0.2996 (2)	0.0445 (6)
C13	0.2981 (3)	0.7435 (3)	0.2322 (2)	0.0464 (6)
C14	0.3029 (3)	0.8543 (3)	0.2396 (2)	0.0651 (7)
C15	0.3908 (3)	0.6662 (3)	0.1503 (2)	0.0511 (6)
C16	0.6105 (4)	0.6225 (3)	0.0376 (3)	0.0742 (8)
C17	0.7291 (3)	0.6814 (3)	−0.0059 (2)	0.0540 (7)
C18	0.7153 (3)	0.8004 (3)	−0.0022 (2)	0.0613 (7)
C19	0.8243 (4)	0.8509 (3)	−0.0514 (3)	0.0816 (9)
C20	0.9458 (4)	0.7817 (4)	−0.1050 (3)	0.103 (1)
C21	0.9597 (4)	0.6624 (4)	−0.1092 (3)	0.099 (1)
C22	0.8527 (4)	0.6119 (3)	−0.0592 (3)	0.0712 (8)
C23	−0.1238 (4)	0.6702 (3)	0.2413 (3)	0.0854 (9)
C24	−0.0455 (5)	0.9020 (4)	0.1812 (4)	0.121 (1)
C25	−0.2271 (4)	0.8814 (3)	0.3883 (3)	0.079 (1)
C26	−0.2458 (4)	0.8042 (4)	0.4791 (3)	0.108 (2)
C27	−0.1963 (6)	0.9921 (5)	0.4198 (5)	0.170 (2)
C28	−0.3707 (4)	0.9073 (4)	0.3484 (4)	0.126 (2)
H1C2	0.1954	0.4843	0.4690	0.046*
H2C2	0.0592	0.5714	0.4307	0.046*
HC4	0.2476	0.8042	0.4306	0.052*
HC7	0.6575	0.4574	0.2738	0.069*
HC8	0.7263	0.2814	0.1751	0.086*
HC10	0.3085	0.2406	0.2294	0.062*
HC11	0.2355	0.4214	0.3218	0.052*
HC12	0.1656	0.6248	0.2604	0.045*
H1C14	0.2330	0.9066	0.2920	0.065*
H2C14	0.3765	0.8865	0.1927	0.065*
H1C16	0.5524	0.6140	−0.0147	0.074*
H2C16	0.6524	0.5430	0.0619	0.074*
HC18	0.6258	0.8514	0.0363	0.061*
HC19	0.8141	0.9379	−0.0476	0.082*
HC20	1.0244	0.8179	−0.1412	0.103*
HC21	1.0484	0.6118	−0.1489	0.099*
HC22	0.8645	0.5246	−0.0614	0.071*
H1C23	−0.2104	0.6920	0.2084	0.085*
H2C23	−0.0398	0.6274	0.1918	0.085*
H3C23	−0.1436	0.6183	0.2993	0.085*
H1C24	−0.1320	0.9243	0.1482	0.121*
H2C24	−0.0235	0.9745	0.2068	0.121*
H3C24	0.0388	0.8602	0.1315	0.121*
H1C26	−0.3241	0.8478	0.5321	0.132*
H2C26	−0.2721	0.7309	0.4593	0.126*
H3C26	−0.1537	0.7831	0.5057	0.158*
H1C27	−0.2755	1.0311	0.4743	0.220*
H2C27	−0.1030	0.9746	0.4450	0.209*
H3C27	−0.1896	1.0455	0.3613	0.219*
H1C28	−0.4501	0.9484	0.4019	0.158*
H2C28	−0.3628	0.9585	0.2885	0.183*
H3C28	−0.3920	0.8318	0.3290	0.142*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si	0.0498 (5)	0.0596 (5)	0.0659 (5)	−0.0102 (4)	−0.0114 (4)	0.0070 (4)
O1	0.083 (1)	0.118 (2)	0.055 (1)	−0.046 (1)	0.017 (1)	−0.011 (1)
O2	0.065 (1)	0.078 (1)	0.049 (1)	−0.027 (1)	−0.0001 (9)	−0.0165 (9)
O3	0.055 (1)	0.071 (1)	0.064 (1)	−0.0302 (9)	−0.0105 (9)	−0.012 (1)
O4	0.041 (1)	0.087 (1)	0.081 (1)	−0.025 (1)	−0.0166 (9)	0.003 (1)
O5	0.176 (2)	0.064 (2)	0.161 (2)	−0.003 (2)	−0.072 (2)	−0.020 (2)
O6	0.132 (3)	0.144 (3)	0.215 (3)	0.026 (2)	0.001 (2)	−0.104 (2)
O7	0.082 (1)	0.078 (1)	0.064 (1)	−0.039 (1)	0.012 (1)	−0.023 (1)
O8	0.057 (1)	0.074 (1)	0.052 (1)	−0.0241 (9)	0.0128 (9)	−0.0151 (9)
O9	0.0393 (9)	0.053 (1)	0.052 (1)	−0.0062 (8)	−0.0028 (8)	−0.0068 (8)
N1	0.034 (1)	0.051 (1)	0.052 (1)	−0.0138 (9)	−0.0080 (9)	−0.002 (1)
N2	0.112 (2)	0.069 (2)	0.128 (3)	0.025 (2)	−0.041 (2)	−0.028 (2)
C1	0.034 (1)	0.046 (1)	0.043 (1)	−0.012 (1)	−0.003 (1)	−0.003 (1)
C2	0.041 (1)	0.054 (2)	0.042 (1)	−0.016 (1)	−0.002 (1)	−0.002 (1)
C3	0.051 (2)	0.068 (2)	0.054 (2)	−0.021 (1)	−0.005 (1)	−0.003 (1)
C4	0.049 (2)	0.063 (2)	0.047 (2)	−0.021 (1)	−0.004 (1)	−0.006 (1)
C5	0.048 (2)	0.063 (2)	0.053 (2)	−0.026 (1)	−0.006 (1)	0.004 (1)
C6	0.044 (1)	0.045 (2)	0.048 (2)	−0.009 (1)	−0.008 (1)	0.005 (1)
C7	0.043 (2)	0.072 (2)	0.086 (2)	−0.005 (1)	−0.007 (2)	−0.011 (2)
C8	0.056 (2)	0.079 (2)	0.111 (3)	0.016 (2)	−0.014 (2)	−0.030 (2)
C9	0.083 (2)	0.049 (2)	0.077 (2)	0.012 (2)	−0.027 (2)	−0.013 (2)
C10	0.075 (2)	0.050 (2)	0.063 (2)	−0.015 (1)	−0.016 (2)	0.001 (1)
C11	0.054 (2)	0.050 (2)	0.052 (2)	−0.015 (1)	−0.005 (1)	−0.002 (1)
C12	0.040 (1)	0.046 (2)	0.046 (1)	−0.013 (1)	−0.001 (1)	−0.005 (1)
C13	0.049 (2)	0.046 (2)	0.044 (2)	−0.015 (1)	−0.002 (1)	−0.001 (1)
C14	0.068 (2)	0.056 (2)	0.068 (2)	−0.023 (1)	0.008 (1)	−0.005 (1)
C15	0.058 (2)	0.055 (2)	0.039 (1)	−0.017 (1)	−0.001 (1)	0.002 (1)
C16	0.077 (2)	0.076 (2)	0.059 (2)	−0.024 (2)	0.024 (1)	−0.018 (2)
C17	0.054 (2)	0.067 (2)	0.039 (1)	−0.016 (1)	0.003 (1)	−0.005 (1)
C18	0.059 (2)	0.061 (2)	0.057 (2)	−0.013 (1)	0.007 (1)	−0.006 (1)
C19	0.077 (2)	0.072 (2)	0.092 (2)	−0.023 (2)	0.005 (2)	−0.001 (2)
C20	0.074 (2)	0.091 (3)	0.128 (3)	−0.030 (2)	0.035 (2)	−0.006 (2)
C21	0.062 (2)	0.090 (3)	0.125 (3)	−0.011 (2)	0.031 (2)	−0.016 (2)
C22	0.060 (2)	0.071 (2)	0.073 (2)	−0.012 (2)	0.011 (2)	−0.008 (2)
C23	0.077 (2)	0.090 (2)	0.096 (2)	−0.014 (2)	−0.034 (2)	−0.018 (2)
C24	0.098 (3)	0.150 (3)	0.123 (3)	−0.037 (3)	−0.040 (2)	0.070 (2)
C25	0.058 (1)	0.059 (2)	0.113 (2)	−0.003 (1)	−0.008 (1)	−0.013 (1)
C26	0.069 (2)	0.140 (3)	0.102 (2)	−0.007 (3)	−0.008 (2)	0.011 (2)
C27	0.158 (4)	0.107 (3)	0.226 (4)	−0.057 (3)	0.065 (4)	−0.097 (3)
C28	0.051 (2)	0.159 (4)	0.139 (3)	0.031 (2)	−0.010 (1)	0.019 (3)

Geometric parameters (Å, º)

Si—O9	1.673 (2)	C12—HC12	1.000
Si—C23	1.849 (4)	C13—C14	1.312 (4)
Si—C24	1.835 (4)	C13—C15	1.477 (4)
Si—C25	1.869 (4)	C14—H1C14	1.000
O1—C3	1.195 (3)	C14—H2C14	1.000
O2—C3	1.363 (3)	C16—C17	1.494 (4)
O2—C4	1.413 (3)	C16—H1C16	1.000
O3—C4	1.411 (3)	C16—H2C16	1.000
O3—C5	1.353 (4)	C17—C18	1.367 (4)
O4—C5	1.198 (3)	C17—C22	1.378 (4)
O5—N2	1.211 (4)	C18—C19	1.384 (4)
O6—N2	1.214 (5)	C18—HC18	1.000
O7—C15	1.195 (3)	C19—C20	1.365 (5)
O8—C15	1.339 (3)	C19—HC19	1.000
O8—C16	1.454 (3)	C20—C21	1.370 (5)
O9—C12	1.413 (3)	C20—HC20	1.000
N1—C1	1.462 (3)	C21—C22	1.373 (5)
N1—C5	1.374 (3)	C21—HC21	1.000
N1—C6	1.417 (3)	C22—HC22	1.000
N2—C9	1.474 (4)	C23—H1C23	1.000
C1—C2	1.532 (4)	C23—H2C23	1.000
C1—C4	1.533 (4)	C23—H3C23	1.000
C1—C12	1.547 (4)	C24—H1C24	1.000
C2—C3	1.480 (4)	C24—H2C24	1.000
C2—H1C2	1.000	C24—H3C24	1.000
C2—H2C2	1.000	C25—C26	1.519 (5)
C4—HC4	1.000	C25—C27	1.477 (5)
C6—C7	1.394 (4)	C25—C28	1.546 (5)
C6—C11	1.385 (4)	C26—H1C26	1.000
C7—C8	1.373 (5)	C26—H2C26	1.000
C7—HC7	1.000	C26—H3C26	1.000
C8—C9	1.370 (5)	C27—H1C27	1.000
C8—HC8	1.000	C27—H2C27	1.000
C9—C10	1.367 (5)	C27—H3C27	1.000
C10—C11	1.376 (4)	C28—H1C28	1.000
C10—HC10	1.000	C28—H2C28	1.000
C11—HC11	1.000	C28—H3C28	1.000
C12—C13	1.518 (4)
O9—Si—C23	109.3 (1)	C13—C14—H1C14	120.0
O9—Si—C24	109.2 (2)	C13—C14—H2C14	120.0
O9—Si—C25	103.9 (1)	H1C14—C14—H2C14	120.0
C23—Si—C24	110.5 (2)	O7—C15—O8	123.6 (3)
C23—Si—C25	111.7 (2)	O7—C15—C13	123.4 (3)
C24—Si—C25	112.1 (2)	O8—C15—C13	113.0 (3)
C3—O2—C4	111.5 (2)	O8—C16—C17	109.0 (3)
C4—O3—C5	110.7 (2)	O8—C16—H1C16	109.6
C15—O8—C16	114.4 (2)	O8—C16—H2C16	109.6
Si—O9—C12	124.0 (2)	C17—C16—H1C16	109.6
C1—N1—C5	111.1 (2)	C17—C16—H2C16	109.6
C1—N1—C6	125.2 (2)	H1C16—C16—H2C16	109.5
C5—N1—C6	122.8 (2)	C16—C17—C18	123.1 (3)
O5—N2—O6	125.5 (4)	C16—C17—C22	117.3 (3)
O5—N2—C9	118.0 (4)	C18—C17—C22	119.4 (3)
O6—N2—C9	116.5 (4)	C17—C18—C19	120.4 (3)
N1—C1—C2	114.5 (2)	C17—C18—HC18	119.8
N1—C1—C4	101.4 (2)	C19—C18—HC18	119.8
N1—C1—C12	113.1 (2)	C18—C19—C20	119.9 (4)
C2—C1—C4	103.2 (2)	C18—C19—HC19	120.1
C2—C1—C12	113.2 (2)	C20—C19—HC19	120.1
C4—C1—C12	110.2 (2)	C19—C20—C21	119.8 (3)
C1—C2—C3	106.2 (2)	C19—C20—HC20	120.1
C1—C2—H1C2	110.3	C21—C20—HC20	120.1
C1—C2—H2C2	110.3	C20—C21—C22	120.5 (3)
C3—C2—H1C2	110.3	C20—C21—HC21	119.8
C3—C2—H2C2	110.3	C22—C21—HC21	119.8
H1C2—C2—H2C2	109.5	C17—C22—C21	120.0 (3)
O1—C3—O2	120.8 (3)	C17—C22—HC22	120.0
O1—C3—C2	128.7 (3)	C21—C22—HC22	120.0
O2—C3—C2	110.5 (2)	Si—C23—H1C23	109.5
O2—C4—O3	108.8 (2)	Si—C23—H2C23	109.5
O2—C4—C1	108.6 (2)	Si—C23—H3C23	109.5
O2—C4—HC4	110.9	H1C23—C23—H2C23	109.5
O3—C4—C1	106.7 (2)	H1C23—C23—H3C23	109.5
O3—C4—HC4	110.9	H2C23—C23—H3C23	109.5
C1—C4—HC4	110.9	Si—C24—H1C24	109.5
O3—C5—O4	121.3 (3)	Si—C24—H2C24	109.5
O3—C5—N1	109.7 (3)	Si—C24—H3C24	109.5
O4—C5—N1	128.9 (3)	H1C24—C24—H2C24	109.5
N1—C6—C7	119.4 (3)	H1C24—C24—H3C24	109.5
N1—C6—C11	121.3 (3)	H2C24—C24—H3C24	109.5
C7—C6—C11	119.3 (3)	Si—C25—C26	111.6 (3)
C6—C7—C8	119.4 (3)	Si—C25—C27	111.2 (3)
C6—C7—HC7	120.3	Si—C25—C28	108.0 (3)
C8—C7—HC7	120.3	C26—C25—C27	108.9 (4)
C7—C8—C9	120.1 (3)	C26—C25—C28	107.0 (3)
C7—C8—HC8	120.0	C27—C25—C28	110.0 (4)
C9—C8—HC8	120.0	C25—C26—H1C26	109.5
N2—C9—C8	119.3 (4)	C25—C26—H2C26	109.5
N2—C9—C10	119.2 (4)	C25—C26—H3C26	109.5
C8—C9—C10	121.5 (3)	H1C26—C26—H2C26	109.5
C9—C10—C11	118.8 (3)	H1C26—C26—H3C26	109.5
C9—C10—HC10	120.6	H2C26—C26—H3C26	109.5
C11—C10—HC10	120.6	C25—C27—H1C27	109.5
C6—C11—C10	120.8 (3)	C25—C27—H2C27	109.5
C6—C11—HC11	119.6	C25—C27—H3C27	109.5
C10—C11—HC11	119.6	H1C27—C27—H2C27	109.5
O9—C12—C1	104.6 (2)	H1C27—C27—H3C27	109.5
O9—C12—C13	112.8 (2)	H2C27—C27—H3C27	109.5
O9—C12—HC12	109.2	C25—C28—H1C28	109.5
C1—C12—C13	111.7 (2)	C25—C28—H2C28	109.5
C1—C12—HC12	109.2	C25—C28—H3C28	109.5
C13—C12—HC12	109.2	H1C28—C28—H2C28	109.5
C12—C13—C14	124.0 (3)	H1C28—C28—H3C28	109.5
C12—C13—C15	114.3 (2)	H2C28—C28—H3C28	109.5
C14—C13—C15	121.5 (3)
C23—Si—O9—C12	46.3 (2)	H2C2—C2—C3—O1	57.5
C24—Si—O9—C12	−74.7 (3)	H2C2—C2—C3—O2	−122.0
C25—Si—O9—C12	165.6 (2)	N1—C6—C7—C8	−179.4 (3)
O9—Si—C23—H1C23	180.0	N1—C6—C7—HC7	0.6
O9—Si—C23—H2C23	−60.0	C11—C6—C7—C8	−0.9 (5)
O9—Si—C23—H3C23	60.0	C11—C6—C7—HC7	179.1
C24—Si—C23—H1C23	−59.8	N1—C6—C11—C10	−179.0 (3)
C24—Si—C23—H2C23	60.2	N1—C6—C11—HC11	1.0
C24—Si—C23—H3C23	−179.8	C7—C6—C11—C10	2.5 (4)
C25—Si—C23—H1C23	65.6	C7—C6—C11—HC11	−177.5
C25—Si—C23—H2C23	−174.4	C6—C7—C8—C9	−1.3 (6)
C25—Si—C23—H3C23	−54.4	C6—C7—C8—HC8	178.7
O9—Si—C24—H1C24	−180.0	HC7—C7—C8—C9	178.7
O9—Si—C24—H2C24	−60.0	HC7—C7—C8—HC8	−1.3
O9—Si—C24—H3C24	60.0	C7—C8—C9—N2	−179.3 (3)
C23—Si—C24—H1C24	59.8	C7—C8—C9—C10	2.0 (6)
C23—Si—C24—H2C24	179.8	HC8—C8—C9—N2	0.7
C23—Si—C24—H3C24	−60.2	HC8—C8—C9—C10	−178.0
C25—Si—C24—H1C24	−65.4	N2—C9—C10—C11	−179.0 (3)
C25—Si—C24—H2C24	54.6	N2—C9—C10—HC10	1.0
C25—Si—C24—H3C24	174.6	C8—C9—C10—C11	−0.4 (5)
O9—Si—C25—C26	−56.4 (3)	C8—C9—C10—HC10	179.6
O9—Si—C25—C27	65.4 (4)	C9—C10—C11—C6	−1.9 (5)
O9—Si—C25—C28	−173.8 (3)	C9—C10—C11—HC11	178.1
C23—Si—C25—C26	61.3 (3)	HC10—C10—C11—C6	178.1
C23—Si—C25—C27	−176.9 (4)	HC10—C10—C11—HC11	−1.9
C23—Si—C25—C28	−56.1 (3)	O9—C12—C13—C14	24.8 (4)
C24—Si—C25—C26	−174.2 (3)	O9—C12—C13—C15	−150.0 (2)
C24—Si—C25—C27	−52.4 (4)	C1—C12—C13—C14	−92.6 (4)
C24—Si—C25—C28	68.4 (3)	C1—C12—C13—C15	92.5 (3)
C4—O2—C3—O1	−178.6 (3)	HC12—C12—C13—C14	146.5
C4—O2—C3—C2	1.0 (3)	HC12—C12—C13—C15	−28.4
C3—O2—C4—O3	−114.7 (3)	C12—C13—C14—H1C14	0.0
C3—O2—C4—C1	1.0 (3)	C12—C13—C14—H2C14	−180.0
C3—O2—C4—HC4	123.1	C15—C13—C14—H1C14	174.5
C5—O3—C4—O2	117.7 (2)	C15—C13—C14—H2C14	−5.5
C5—O3—C4—C1	0.8 (3)	C12—C13—C15—O7	28.0 (4)
C5—O3—C4—HC4	−120.0	C12—C13—C15—O8	−152.2 (2)
C4—O3—C5—O4	−177.6 (3)	C14—C13—C15—O7	−147.0 (3)
C4—O3—C5—N1	3.2 (3)	C14—C13—C15—O8	32.8 (4)
C16—O8—C15—O7	2.3 (4)	O8—C16—C17—C18	−28.4 (4)
C16—O8—C15—C13	−177.5 (2)	O8—C16—C17—C22	157.1 (3)
C15—O8—C16—C17	164.3 (3)	H1C16—C16—C17—C18	91.5
C15—O8—C16—H1C16	44.3	H1C16—C16—C17—C22	−83.0
C15—O8—C16—H2C16	−75.8	H2C16—C16—C17—C18	−148.4
Si—O9—C12—C1	−149.1 (2)	H2C16—C16—C17—C22	37.2
Si—O9—C12—C13	89.4 (2)	C16—C17—C18—C19	−174.3 (3)
Si—O9—C12—HC12	−32.3	C16—C17—C18—HC18	5.7
C5—N1—C1—C2	−104.1 (3)	C22—C17—C18—C19	0.0 (5)
C5—N1—C1—C4	6.2 (3)	C22—C17—C18—HC18	180.0
C5—N1—C1—C12	124.2 (2)	C16—C17—C22—C21	173.6 (4)
C6—N1—C1—C2	64.8 (3)	C16—C17—C22—HC22	−6.4
C6—N1—C1—C4	175.1 (2)	C18—C17—C22—C21	−1.0 (5)
C6—N1—C1—C12	−67.0 (3)	C18—C17—C22—HC22	179.0
C1—N1—C5—O3	−6.2 (3)	C17—C18—C19—C20	0.8 (6)
C1—N1—C5—O4	174.7 (3)	C17—C18—C19—HC19	−179.2
C6—N1—C5—O3	−175.4 (2)	HC18—C18—C19—C20	−179.2
C6—N1—C5—O4	5.5 (5)	HC18—C18—C19—HC19	0.8
C1—N1—C6—C7	161.7 (3)	C18—C19—C20—C21	−0.6 (7)
C1—N1—C6—C11	−16.8 (4)	C18—C19—C20—HC20	179.4
C5—N1—C6—C7	−30.7 (4)	HC19—C19—C20—C21	179.4
C5—N1—C6—C11	150.8 (3)	HC19—C19—C20—HC20	−0.6
O5—N2—C9—C8	160.6 (4)	C19—C20—C21—C22	−0.5 (8)
O5—N2—C9—C10	−20.7 (5)	C19—C20—C21—HC21	179.5
O6—N2—C9—C8	−19.9 (6)	HC20—C20—C21—C22	179.5
O6—N2—C9—C10	158.8 (4)	HC20—C20—C21—HC21	−0.5
N1—C1—C2—C3	112.2 (3)	C20—C21—C22—C17	1.3 (7)
N1—C1—C2—H1C2	−7.3	C20—C21—C22—HC22	−178.7
N1—C1—C2—H2C2	−128.3	HC21—C21—C22—C17	−178.7
C4—C1—C2—C3	2.9 (3)	HC21—C21—C22—HC22	1.3
C4—C1—C2—H1C2	−116.6	Si—C25—C26—H1C26	−180.0
C4—C1—C2—H2C2	122.4	Si—C25—C26—H2C26	−60.0
C12—C1—C2—C3	−116.1 (2)	Si—C25—C26—H3C26	60.0
C12—C1—C2—H1C2	124.4	C27—C25—C26—H1C26	56.9
C12—C1—C2—H2C2	3.3	C27—C25—C26—H2C26	176.9
N1—C1—C4—O2	−121.2 (2)	C27—C25—C26—H3C26	−63.1
N1—C1—C4—O3	−4.2 (3)	C28—C25—C26—H1C26	−62.0
N1—C1—C4—HC4	116.7	C28—C25—C26—H2C26	58.0
C2—C1—C4—O2	−2.5 (3)	C28—C25—C26—H3C26	178.0
C2—C1—C4—O3	114.6 (2)	Si—C25—C27—H1C27	−180.0
C2—C1—C4—HC4	−124.5	Si—C25—C27—H2C27	−60.0
C12—C1—C4—O2	118.7 (2)	Si—C25—C27—H3C27	60.0
C12—C1—C4—O3	−124.2 (2)	C26—C25—C27—H1C27	−56.7
C12—C1—C4—HC4	−3.4	C26—C25—C27—H2C27	63.3
N1—C1—C12—O9	−168.4 (2)	C26—C25—C27—H3C27	−176.7
N1—C1—C12—C13	−46.1 (3)	C28—C25—C27—H1C27	60.4
N1—C1—C12—HC12	74.8	C28—C25—C27—H2C27	−179.6
C2—C1—C12—O9	59.2 (3)	C28—C25—C27—H3C27	−59.6
C2—C1—C12—C13	−178.5 (2)	Si—C25—C28—H1C28	180.0
C2—C1—C12—HC12	−57.6	Si—C25—C28—H2C28	−60.0
C4—C1—C12—O9	−55.7 (3)	Si—C25—C28—H3C28	60.0
C4—C1—C12—C13	66.6 (3)	C26—C25—C28—H1C28	59.7
C4—C1—C12—HC12	−172.5	C26—C25—C28—H2C28	179.7
C1—C2—C3—O1	177.0 (3)	C26—C25—C28—H3C28	−60.3
C1—C2—C3—O2	−2.5 (3)	C27—C25—C28—H1C28	−58.5
H1C2—C2—C3—O1	−63.6	C27—C25—C28—H2C28	61.5
H1C2—C2—C3—O2	116.9	C27—C25—C28—H3C28	−178.5