Bulky 2,6-disubstituted aryl siloxanes and a disilanamine

High steric constraints lead to inter­locking tri­methyl­silyl and tertbutyl (or isoprop­yl) substituents in the structures of three silyl-protected phenol and anilene reagents. The two di-tert-butyl compounds are distorted from planarity to mild boat conformations but the diiso­propyl­anilene remains rigorously planar.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.073
• Data-to-parameter ratio = 20.6

Structure: II

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.093
• Data-to-parameter ratio = 18.1

Structure: III

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.126
• Data-to-parameter ratio = 20.6

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.344 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             139.7 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         27 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

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




Datablock: II


Alert level C
PLAT220_ALERT_2_C NonSolvent Resd 1  C   Ueq(max) / Ueq(min) Range        3.9 Ratio
PLAT242_ALERT_2_C Low    MainMol Ueq as Compared to Neighbors of        Si1 Check
PLAT761_ALERT_1_C CIF Contains no X-H Bonds ......................     Please Check
PLAT762_ALERT_1_C CIF Contains no X-Y-H or H-Y-H Angles ..........     Please Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT300_ALERT_4_G Atom Site Occupancy of H15A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H15C       Constrained at        0.5 Check
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             137.9 Degree
PLAT789_ALERT_4_G Atoms with Negative _atom_site_disorder_group  #          3 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          9 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

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




Datablock: III



Alert level C
PLAT220_ALERT_2_C NonSolvent Resd 1  C   Ueq(max) / Ueq(min) Range        3.9 Ratio
PLAT242_ALERT_2_C Low    MainMol Ueq as Compared to Neighbors of        Si1 Check
PLAT761_ALERT_1_C CIF Contains no X-H Bonds ......................     Please Check
PLAT762_ALERT_1_C CIF Contains no X-Y-H or H-Y-H Angles ..........     Please Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT300_ALERT_4_G Atom Site Occupancy of H7A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H7B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H7C        Constrained at        0.5 Check
PLAT789_ALERT_4_G Atoms with Negative _atom_site_disorder_group  #          3 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         54 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018) for (I), (II); APEX2 (Bruker, 2014) for (III). Cell refinement: CrysAlis PRO (Rigaku OD, 2018) for (I), (II); SAINT (Bruker, 2014) for (III). Data reduction: CrysAlis PRO (Rigaku OD, 2018) for (I), (II); SAINT (Bruker, 2014) for (III). For all structures, program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

5-Bromo-1,3-di-tert-butyl-2-[(trimethylsilyl)oxy]benzene (I)

Crystal data

C17H29BrOSi	F(000) = 752
Mr = 357.40	Dx = 1.310 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 13.0955 (1) Å	Cell parameters from 18499 reflections
b = 15.3457 (2) Å	θ = 4.4–79.8°
c = 9.0449 (1) Å	µ = 3.67 mm^−1
β = 94.617 (1)°	T = 100 K
V = 1811.76 (3) Å^3	Prism, clear colourless
Z = 4	0.42 × 0.21 × 0.13 mm

Data collection

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Pilatus 200K diffractometer	3935 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	3924 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.024
ω scans	θmax = 80.1°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018)	h = −16→16
Tmin = 0.507, Tmax = 1.000	k = −19→18
20327 measured reflections	l = −8→11

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.031	w = 1/[σ^2(Fo^2) + (0.0196P)^2 + 3.634P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.073	(Δ/σ)max = 0.002
S = 1.10	Δρmax = 0.66 e Å^−3
3935 reflections	Δρmin = −0.36 e Å^−3
191 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00139 (10)
Primary atom site location: dual

Special details

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

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

	x	y	z	Uiso*/Ueq
Br1	0.51566 (2)	0.21330 (2)	0.45554 (3)	0.01991 (9)
Si1	0.81135 (4)	0.60159 (4)	0.69256 (6)	0.01462 (13)
O1	0.80844 (10)	0.51233 (9)	0.58830 (15)	0.0137 (3)
C1	0.74581 (14)	0.44182 (13)	0.5533 (2)	0.0122 (4)
C2	0.67726 (14)	0.44492 (13)	0.4237 (2)	0.0124 (4)
C3	0.60978 (15)	0.37556 (13)	0.3970 (2)	0.0139 (4)
H3	0.562847	0.376592	0.314197	0.017*
C4	0.61193 (15)	0.30530 (13)	0.4923 (2)	0.0143 (4)
C5	0.68503 (15)	0.29845 (13)	0.6102 (2)	0.0136 (4)
H5	0.686809	0.249093	0.670039	0.016*
C6	0.75644 (15)	0.36495 (13)	0.6406 (2)	0.0128 (4)
C7	0.67316 (15)	0.52100 (13)	0.3119 (2)	0.0141 (4)
C8	0.60959 (17)	0.49792 (14)	0.1665 (2)	0.0183 (4)
H8A	0.636634	0.446032	0.125038	0.027*
H8B	0.612894	0.545090	0.097353	0.027*
H8C	0.539601	0.488246	0.186543	0.027*
C9	0.61968 (17)	0.59939 (14)	0.3782 (2)	0.0196 (4)
H9A	0.548598	0.586074	0.385149	0.029*
H9B	0.625605	0.649347	0.315599	0.029*
H9C	0.651459	0.611686	0.475345	0.029*
C10	0.78100 (17)	0.54395 (15)	0.2675 (2)	0.0200 (4)
H10A	0.823327	0.561482	0.353977	0.030*
H10B	0.776290	0.590827	0.196991	0.030*
H10C	0.810620	0.493866	0.223875	0.030*
C11	0.84163 (15)	0.35033 (13)	0.7659 (2)	0.0140 (4)
C12	0.85418 (16)	0.25267 (14)	0.8049 (2)	0.0184 (4)
H12A	0.793262	0.231898	0.845688	0.028*
H12B	0.911767	0.245176	0.876394	0.028*
H12C	0.865318	0.220270	0.716834	0.028*
C13	0.94702 (15)	0.37909 (14)	0.7187 (2)	0.0183 (4)
H13A	0.963697	0.345661	0.634250	0.027*
H13B	0.998222	0.369667	0.799205	0.027*
H13C	0.944785	0.439842	0.693388	0.027*
C14	0.81303 (17)	0.39676 (14)	0.9074 (2)	0.0181 (4)
H14A	0.800068	0.457243	0.886197	0.027*
H14B	0.868505	0.391592	0.982939	0.027*
H14C	0.752635	0.370455	0.941273	0.027*
C15	0.69125 (17)	0.61128 (15)	0.7890 (2)	0.0223 (5)
H15A	0.645076	0.650692	0.735070	0.033*
H15B	0.707232	0.633097	0.887583	0.033*
H15C	0.659611	0.555032	0.793856	0.033*
C16	0.83126 (18)	0.69902 (14)	0.5749 (3)	0.0238 (5)
H16A	0.888992	0.689285	0.518019	0.036*
H16B	0.843886	0.749167	0.637185	0.036*
H16C	0.771138	0.708748	0.509058	0.036*
C17	0.92756 (18)	0.59976 (15)	0.8263 (3)	0.0247 (5)
H17A	0.921155	0.553917	0.897176	0.037*
H17B	0.934120	0.654670	0.877009	0.037*
H17C	0.987189	0.589737	0.773474	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01809 (13)	0.01465 (12)	0.02615 (14)	−0.00553 (8)	−0.00349 (8)	0.00120 (8)
Si1	0.0148 (3)	0.0125 (3)	0.0165 (3)	−0.00183 (19)	0.0007 (2)	−0.0017 (2)
O1	0.0135 (6)	0.0125 (6)	0.0153 (6)	−0.0022 (5)	0.0009 (5)	−0.0006 (5)
C1	0.0107 (8)	0.0117 (9)	0.0145 (9)	−0.0004 (7)	0.0029 (7)	−0.0023 (7)
C2	0.0120 (9)	0.0134 (9)	0.0121 (9)	0.0027 (7)	0.0024 (7)	−0.0002 (7)
C3	0.0128 (9)	0.0154 (9)	0.0132 (9)	0.0006 (7)	−0.0002 (7)	−0.0003 (7)
C4	0.0118 (9)	0.0130 (9)	0.0183 (10)	−0.0021 (7)	0.0021 (7)	−0.0029 (7)
C5	0.0140 (9)	0.0127 (9)	0.0142 (9)	0.0002 (7)	0.0018 (7)	0.0017 (7)
C6	0.0124 (9)	0.0146 (9)	0.0119 (9)	0.0015 (7)	0.0037 (7)	−0.0013 (7)
C7	0.0158 (9)	0.0129 (9)	0.0136 (9)	0.0005 (7)	0.0012 (7)	0.0015 (7)
C8	0.0228 (10)	0.0177 (10)	0.0142 (9)	0.0003 (8)	0.0000 (8)	0.0022 (8)
C9	0.0240 (11)	0.0149 (10)	0.0198 (10)	0.0054 (8)	−0.0002 (8)	−0.0007 (8)
C10	0.0210 (10)	0.0230 (11)	0.0166 (10)	−0.0039 (8)	0.0045 (8)	0.0029 (8)
C11	0.0139 (9)	0.0147 (9)	0.0131 (9)	0.0006 (7)	−0.0004 (7)	0.0006 (7)
C12	0.0175 (10)	0.0176 (10)	0.0197 (10)	0.0027 (8)	−0.0015 (8)	0.0037 (8)
C13	0.0132 (9)	0.0198 (10)	0.0215 (10)	0.0009 (8)	−0.0005 (8)	0.0020 (8)
C14	0.0204 (10)	0.0194 (10)	0.0142 (9)	0.0001 (8)	−0.0006 (8)	−0.0004 (8)
C15	0.0215 (11)	0.0246 (11)	0.0214 (11)	0.0014 (9)	0.0049 (8)	−0.0021 (9)
C16	0.0261 (11)	0.0157 (10)	0.0294 (12)	−0.0049 (9)	0.0021 (9)	0.0007 (9)
C17	0.0230 (11)	0.0209 (11)	0.0291 (12)	−0.0048 (9)	−0.0042 (9)	−0.0035 (9)

Geometric parameters (Å, º)

Br1—C4	1.904 (2)	C10—H10A	0.9600
Si1—O1	1.6617 (15)	C10—H10B	0.9600
Si1—C15	1.865 (2)	C10—H10C	0.9600
Si1—C16	1.865 (2)	C11—C12	1.545 (3)
Si1—C17	1.866 (2)	C11—C13	1.542 (3)
O1—C1	1.379 (2)	C11—C14	1.537 (3)
C1—C2	1.419 (3)	C12—H12A	0.9600
C1—C6	1.420 (3)	C12—H12B	0.9600
C2—C3	1.392 (3)	C12—H12C	0.9600
C2—C7	1.543 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C3—C4	1.379 (3)	C13—H13C	0.9600
C4—C5	1.378 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C5—C6	1.397 (3)	C14—H14C	0.9600
C6—C11	1.541 (3)	C15—H15A	0.9600
C7—C8	1.540 (3)	C15—H15B	0.9600
C7—C9	1.538 (3)	C15—H15C	0.9600
C7—C10	1.540 (3)	C16—H16A	0.9600
C8—H8A	0.9600	C16—H16B	0.9600
C8—H8B	0.9600	C16—H16C	0.9600
C8—H8C	0.9600	C17—H17A	0.9600
C9—H9A	0.9600	C17—H17B	0.9600
C9—H9B	0.9600	C17—H17C	0.9600
C9—H9C	0.9600
O1—Si1—C15	110.45 (9)	H10A—C10—H10B	109.5
O1—Si1—C16	109.57 (9)	H10A—C10—H10C	109.5
O1—Si1—C17	109.61 (9)	H10B—C10—H10C	109.5
C15—Si1—C16	111.39 (11)	C6—C11—C12	111.50 (16)
C15—Si1—C17	111.88 (11)	C6—C11—C13	111.48 (16)
C16—Si1—C17	103.75 (11)	C13—C11—C12	105.05 (16)
C1—O1—Si1	139.75 (13)	C14—C11—C6	109.51 (16)
O1—C1—C2	119.25 (17)	C14—C11—C12	106.75 (16)
O1—C1—C6	119.59 (17)	C14—C11—C13	112.41 (17)
C2—C1—C6	120.97 (18)	C11—C12—H12A	109.5
C1—C2—C7	123.59 (17)	C11—C12—H12B	109.5
C3—C2—C1	117.91 (18)	C11—C12—H12C	109.5
C3—C2—C7	118.50 (17)	H12A—C12—H12B	109.5
C2—C3—H3	119.7	H12A—C12—H12C	109.5
C4—C3—C2	120.58 (18)	H12B—C12—H12C	109.5
C4—C3—H3	119.7	C11—C13—H13A	109.5
C3—C4—Br1	119.37 (15)	C11—C13—H13B	109.5
C5—C4—Br1	119.17 (15)	C11—C13—H13C	109.5
C5—C4—C3	121.40 (18)	H13A—C13—H13B	109.5
C4—C5—H5	119.7	H13A—C13—H13C	109.5
C4—C5—C6	120.60 (18)	H13B—C13—H13C	109.5
C6—C5—H5	119.7	C11—C14—H14A	109.5
C1—C6—C11	124.24 (17)	C11—C14—H14B	109.5
C5—C6—C1	117.59 (18)	C11—C14—H14C	109.5
C5—C6—C11	118.17 (17)	H14A—C14—H14B	109.5
C8—C7—C2	111.93 (16)	H14A—C14—H14C	109.5
C8—C7—C10	105.93 (16)	H14B—C14—H14C	109.5
C9—C7—C2	109.21 (16)	Si1—C15—H15A	109.5
C9—C7—C8	106.33 (16)	Si1—C15—H15B	109.5
C9—C7—C10	112.26 (17)	Si1—C15—H15C	109.5
C10—C7—C2	111.09 (16)	H15A—C15—H15B	109.5
C7—C8—H8A	109.5	H15A—C15—H15C	109.5
C7—C8—H8B	109.5	H15B—C15—H15C	109.5
C7—C8—H8C	109.5	Si1—C16—H16A	109.5
H8A—C8—H8B	109.5	Si1—C16—H16B	109.5
H8A—C8—H8C	109.5	Si1—C16—H16C	109.5
H8B—C8—H8C	109.5	H16A—C16—H16B	109.5
C7—C9—H9A	109.5	H16A—C16—H16C	109.5
C7—C9—H9B	109.5	H16B—C16—H16C	109.5
C7—C9—H9C	109.5	Si1—C17—H17A	109.5
H9A—C9—H9B	109.5	Si1—C17—H17B	109.5
H9A—C9—H9C	109.5	Si1—C17—H17C	109.5
H9B—C9—H9C	109.5	H17A—C17—H17B	109.5
C7—C10—H10A	109.5	H17A—C17—H17C	109.5
C7—C10—H10B	109.5	H17B—C17—H17C	109.5
C7—C10—H10C	109.5
Br1—C4—C5—C6	−179.69 (15)	C2—C3—C4—C5	−4.7 (3)
Si1—O1—C1—C2	95.3 (2)	C3—C2—C7—C8	−13.1 (2)
Si1—O1—C1—C6	−89.5 (2)	C3—C2—C7—C9	104.4 (2)
O1—C1—C2—C3	−175.38 (17)	C3—C2—C7—C10	−131.27 (19)
O1—C1—C2—C7	4.2 (3)	C3—C4—C5—C6	3.1 (3)
O1—C1—C6—C5	173.89 (17)	C4—C5—C6—C1	4.7 (3)
O1—C1—C6—C11	−6.3 (3)	C4—C5—C6—C11	−175.10 (17)
C1—C2—C3—C4	−1.6 (3)	C5—C6—C11—C12	18.1 (2)
C1—C2—C7—C8	167.30 (18)	C5—C6—C11—C13	135.20 (19)
C1—C2—C7—C9	−75.2 (2)	C5—C6—C11—C14	−99.8 (2)
C1—C2—C7—C10	49.1 (2)	C6—C1—C2—C3	9.5 (3)
C1—C6—C11—C12	−161.65 (18)	C6—C1—C2—C7	−170.85 (17)
C1—C6—C11—C13	−44.6 (3)	C7—C2—C3—C4	178.75 (18)
C1—C6—C11—C14	80.4 (2)	C15—Si1—O1—C1	−2.0 (2)
C2—C1—C6—C5	−11.0 (3)	C16—Si1—O1—C1	−125.1 (2)
C2—C1—C6—C11	168.74 (17)	C17—Si1—O1—C1	121.7 (2)
C2—C3—C4—Br1	178.09 (15)

1,3-Di-tert-butyl-2-[(trimethylsilyl)oxy]benzene (II)

Crystal data

C17H30OSi	Dx = 1.086 Mg m^−3
Mr = 278.50	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pnma	Cell parameters from 12570 reflections
a = 14.47237 (14) Å	θ = 5.1–74.4°
b = 17.4657 (2) Å	µ = 1.13 mm^−1
c = 6.73933 (7) Å	T = 100 K
V = 1703.50 (3) Å^3	Needle, clear colourless
Z = 4	0.31 × 0.11 × 0.07 mm
F(000) = 616

Data collection

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Pilatus 200K diffractometer	1793 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1663 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.046
ω scans	θmax = 74.7°, θmin = 5.1°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018)	h = −18→17
Tmin = 0.773, Tmax = 1.000	k = −21→20
17855 measured reflections	l = −8→8

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.0463P)^2 + 0.6892P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1793 reflections	Δρmax = 0.26 e Å^−3
99 parameters	Δρmin = −0.28 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Si1	0.44620 (3)	0.250000	0.02273 (7)	0.01982 (15)
O1	0.55464 (8)	0.250000	0.10549 (17)	0.0194 (3)
C1	0.59998 (11)	0.250000	0.2860 (2)	0.0181 (3)
C2	0.62564 (8)	0.32076 (6)	0.37337 (17)	0.0195 (3)
C3	0.66393 (8)	0.31815 (7)	0.56362 (18)	0.0228 (3)
H3	0.679079	0.364859	0.628093	0.027*
C4	0.68049 (12)	0.250000	0.6610 (3)	0.0244 (4)
H4	0.702993	0.250001	0.793454	0.029*
C7	0.61394 (8)	0.39980 (7)	0.27322 (18)	0.0219 (3)
C8	0.67393 (10)	0.46122 (7)	0.3744 (2)	0.0309 (3)
H8A	0.652833	0.468650	0.511229	0.046*
H8B	0.668568	0.509554	0.301445	0.046*
H8C	0.738594	0.444559	0.374947	0.046*
C9	0.64519 (9)	0.39815 (7)	0.05482 (18)	0.0249 (3)
H9A	0.710577	0.383808	0.047981	0.037*
H9B	0.636715	0.448972	−0.004068	0.037*
H9C	0.608163	0.360625	−0.018420	0.037*
C10	0.51286 (9)	0.42590 (7)	0.29218 (19)	0.0268 (3)
H10A	0.472354	0.388099	0.229055	0.040*
H10B	0.505156	0.475597	0.226734	0.040*
H10C	0.496631	0.430630	0.432822	0.040*
C15	0.36580 (12)	0.250000	0.2393 (3)	0.0259 (4)
H15A	0.306965	0.226595	0.200528	0.039*	0.5
H15B	0.354989	0.302788	0.282753	0.039*	0.5
H15C	0.393242	0.220617	0.348249	0.039*	0.5
C16	0.42870 (9)	0.16623 (8)	−0.1452 (2)	0.0282 (3)
H16A	0.475983	0.166658	−0.249330	0.042*
H16B	0.367304	0.169330	−0.206060	0.042*
H16C	0.433624	0.118748	−0.068507	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0205 (2)	0.0176 (3)	0.0213 (3)	0.000	−0.00179 (16)	0.000
O1	0.0212 (6)	0.0171 (6)	0.0198 (6)	0.000	−0.0020 (4)	0.000
C1	0.0178 (7)	0.0194 (8)	0.0170 (8)	0.000	0.0020 (6)	0.000
C2	0.0194 (5)	0.0178 (6)	0.0214 (6)	0.0005 (4)	0.0031 (4)	−0.0006 (5)
C3	0.0258 (6)	0.0213 (6)	0.0213 (6)	−0.0011 (5)	0.0027 (5)	−0.0037 (5)
C4	0.0277 (9)	0.0274 (9)	0.0182 (8)	0.000	0.0006 (7)	0.000
C7	0.0266 (6)	0.0154 (6)	0.0237 (6)	−0.0013 (5)	−0.0008 (5)	−0.0012 (5)
C8	0.0402 (8)	0.0188 (6)	0.0338 (7)	−0.0063 (5)	−0.0060 (6)	−0.0002 (5)
C9	0.0303 (6)	0.0189 (6)	0.0256 (6)	−0.0033 (5)	0.0024 (5)	0.0028 (5)
C10	0.0315 (7)	0.0197 (6)	0.0291 (7)	0.0050 (5)	0.0000 (5)	−0.0031 (5)
C15	0.0230 (8)	0.0266 (9)	0.0280 (9)	0.000	0.0007 (7)	0.000
C16	0.0297 (6)	0.0263 (7)	0.0286 (7)	0.0000 (5)	−0.0057 (5)	−0.0048 (5)

Geometric parameters (Å, º)

Si1—O1	1.6655 (12)	C8—H8A	0.9800
Si1—C15	1.8664 (19)	C8—H8B	0.9800
Si1—C16	1.8671 (13)	C8—H8C	0.9800
Si1—C16^i	1.8671 (13)	C9—H9A	0.9800
O1—C1	1.3821 (19)	C9—H9B	0.9800
C1—C2	1.4185 (14)	C9—H9C	0.9800
C1—C2^i	1.4185 (14)	C10—H10A	0.9800
C2—C3	1.3976 (17)	C10—H10B	0.9800
C2—C7	1.5461 (16)	C10—H10C	0.9800
C3—H3	0.9500	C15—H15A	0.9800
C3—C4	1.3802 (15)	C15—H15B	0.9800
C4—H4	0.9500	C15—H15C	0.9800
C7—C8	1.5393 (17)	C16—H16A	0.9800
C7—C9	1.5400 (16)	C16—H16B	0.9800
C7—C10	1.5376 (17)	C16—H16C	0.9800
O1—Si1—C15	109.00 (7)	H8A—C8—H8B	109.5
O1—Si1—C16^i	109.32 (5)	H8A—C8—H8C	109.5
O1—Si1—C16	109.32 (5)	H8B—C8—H8C	109.5
C15—Si1—C16^i	112.92 (5)	C7—C9—H9A	109.5
C15—Si1—C16	112.92 (5)	C7—C9—H9B	109.5
C16—Si1—C16^i	103.18 (9)	C7—C9—H9C	109.5
C1—O1—Si1	137.91 (10)	H9A—C9—H9B	109.5
O1—C1—C2	119.32 (7)	H9A—C9—H9C	109.5
O1—C1—C2^i	119.32 (7)	H9B—C9—H9C	109.5
C2—C1—C2^i	121.21 (15)	C7—C10—H10A	109.5
C1—C2—C7	124.62 (10)	C7—C10—H10B	109.5
C3—C2—C1	117.15 (11)	C7—C10—H10C	109.5
C3—C2—C7	118.24 (10)	H10A—C10—H10B	109.5
C2—C3—H3	118.9	H10A—C10—H10C	109.5
C4—C3—C2	122.23 (12)	H10B—C10—H10C	109.5
C4—C3—H3	118.9	Si1—C15—H15A	109.5
C3—C4—C3^i	119.16 (16)	Si1—C15—H15B	109.5
C3—C4—H4	120.4	Si1—C15—H15C	109.5
C3^i—C4—H4	120.4	H15A—C15—H15B	109.5
C8—C7—C2	111.54 (10)	H15A—C15—H15C	109.5
C8—C7—C9	105.71 (10)	H15B—C15—H15C	109.5
C9—C7—C2	111.61 (9)	Si1—C16—H16A	109.5
C10—C7—C2	109.43 (10)	Si1—C16—H16B	109.5
C10—C7—C8	107.06 (10)	Si1—C16—H16C	109.5
C10—C7—C9	111.37 (10)	H16A—C16—H16B	109.5
C7—C8—H8A	109.5	H16A—C16—H16C	109.5
C7—C8—H8B	109.5	H16B—C16—H16C	109.5
C7—C8—H8C	109.5
Si1—O1—C1—C2	−92.19 (12)	C2^i—C1—C2—C7	170.19 (9)
Si1—O1—C1—C2^i	92.19 (12)	C2—C3—C4—C3^i	3.9 (2)
O1—C1—C2—C3	174.50 (12)	C3—C2—C7—C8	17.63 (15)
O1—C1—C2—C7	−5.3 (2)	C3—C2—C7—C9	135.63 (11)
C1—C2—C3—C4	2.89 (19)	C3—C2—C7—C10	−100.63 (12)
C1—C2—C7—C8	−162.53 (12)	C7—C2—C3—C4	−177.26 (12)
C1—C2—C7—C9	−44.53 (16)	C15—Si1—O1—C1	0.000 (1)
C1—C2—C7—C10	79.20 (15)	C16^i—Si1—O1—C1	123.87 (5)
C2^i—C1—C2—C3	−10.0 (2)	C16—Si1—O1—C1	−123.87 (5)

Symmetry code: (i) x, −y+1/2, z.

N-(2,6-Diisopropylphenyl)-1,1,1-trimethyl-N-(trimethylsilyl)silanamine (III)

Crystal data

C18H35NSi2	Dx = 1.022 Mg m^−3
Mr = 321.65	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Cmcm	Cell parameters from 4098 reflections
a = 12.199 (3) Å	θ = 2.4–27.5°
b = 12.091 (3) Å	µ = 0.17 mm^−1
c = 14.177 (3) Å	T = 173 K
V = 2091.1 (8) Å^3	Block, clear colourless
Z = 4	0.19 × 0.16 × 0.10 mm
F(000) = 712

Data collection

Bruker APEXII CCD diffractometer	1082 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 27.6°, θmin = 2.4°
Absorption correction: ψ scan (SADABS; Bruker, 2014)	h = −15→15
Tmin = 0.667, Tmax = 0.746	k = −15→15
8996 measured reflections	l = −18→17
1317 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.0516P)^2 + 2.3874P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1317 reflections	Δρmax = 0.36 e Å^−3
64 parameters	Δρmin = −0.26 e Å^−3
54 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Si1	0.62813 (7)	0.91524 (6)	0.750000	0.0459 (3)
N1	0.500000	0.8496 (2)	0.750000	0.0315 (6)
C1	0.500000	0.7298 (2)	0.750000	0.0262 (6)
C2	0.500000	0.67207 (17)	0.66401 (16)	0.0308 (5)
C3	0.500000	0.55648 (18)	0.6663 (2)	0.0402 (6)
H3	0.500000	0.516529	0.608650	0.048*
C4	0.500000	0.4993 (3)	0.750000	0.0446 (9)
H4	0.500000	0.420746	0.750000	0.053*
C5	0.500000	0.7292 (2)	0.56902 (17)	0.0396 (6)
H5	0.500000	0.810796	0.580380	0.047*
C6	0.39760 (16)	0.70083 (19)	0.51164 (15)	0.0572 (5)
H6A	0.395926	0.621120	0.499170	0.086*
H6B	0.399211	0.741161	0.451700	0.086*
H6C	0.332066	0.722035	0.547291	0.086*
C7	0.7385 (2)	0.8087 (3)	0.750000	0.0656 (9)
H7A	0.806954	0.841786	0.727270	0.098*	0.5
H7B	0.717550	0.747465	0.708470	0.098*	0.5
H7C	0.749174	0.780828	0.814260	0.098*	0.5
C8	0.6484 (3)	1.0030 (3)	0.8562 (2)	0.1024 (11)
H8A	0.595639	1.064092	0.855311	0.154*
H8B	0.723089	1.032743	0.856153	0.154*
H8C	0.637079	0.958308	0.913029	0.154*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0650 (5)	0.0344 (4)	0.0382 (4)	−0.0227 (3)	0.000	0.000
N1	0.0452 (14)	0.0211 (11)	0.0281 (13)	0.000	0.000	0.000
C1	0.0233 (13)	0.0231 (13)	0.0323 (15)	0.000	0.000	0.000
C2	0.0253 (9)	0.0293 (10)	0.0377 (12)	0.000	0.000	−0.0060 (9)
C3	0.0345 (11)	0.0283 (11)	0.0578 (16)	0.000	0.000	−0.0132 (10)
C4	0.0329 (16)	0.0222 (14)	0.079 (3)	0.000	0.000	0.000
C5	0.0492 (13)	0.0382 (12)	0.0313 (12)	0.000	0.000	−0.0087 (10)
C6	0.0526 (11)	0.0753 (14)	0.0437 (11)	0.0083 (10)	−0.0095 (9)	−0.0060 (10)
C7	0.0414 (15)	0.076 (2)	0.080 (2)	−0.0221 (15)	0.000	0.000
C8	0.117 (2)	0.0922 (19)	0.098 (2)	−0.0496 (19)	0.0103 (19)	−0.0548 (17)

Geometric parameters (Å, º)

Si1—N1	1.7529 (13)	C1—C2^i	1.405 (3)
Si1—C7	1.864 (4)	C2—C3	1.398 (3)
Si1—C8	1.858 (2)	C2—C5	1.513 (3)
Si1—C8^i	1.858 (2)	C3—C4	1.373 (3)
N1—C1	1.448 (4)	C5—C6	1.530 (2)
C1—C2	1.405 (3)	C5—C6^ii	1.530 (2)
N1—Si1—C7	109.36 (12)	C2—C1—N1	119.81 (13)
N1—Si1—C8	112.15 (10)	C2^i—C1—C2	120.4 (3)
N1—Si1—C8^i	112.15 (10)	C1—C2—C5	123.05 (19)
C8—Si1—C7	107.37 (13)	C3—C2—C1	118.5 (2)
C8^i—Si1—C7	107.37 (13)	C3—C2—C5	118.5 (2)
C8—Si1—C8^i	108.2 (2)	C4—C3—C2	121.6 (2)
Si1^iii—N1—Si1	126.17 (15)	C3^i—C4—C3	119.5 (3)
C1—N1—Si1^iii	116.92 (7)	C2—C5—C6^ii	111.78 (14)
C1—N1—Si1	116.92 (7)	C2—C5—C6	111.78 (14)
C2^i—C1—N1	119.81 (13)	C6—C5—C6^ii	109.5 (2)

Symmetry codes: (i) x, y, −z+3/2; (ii) −x+1, y, z; (iii) −x+1, y, −z+3/2.