6-[4-(tert-Butyl­dimethyl­sil­yloxy)phen­yl]-1-oxa­spiro­[2.5]hepta­ne

Wetzel, E.A.; Lindeman, S.; Donaldson, W.A.

doi:10.1107/S241431462400590X

6-[4-(tert-Butyldimethylsilyloxy)phenyl]-1-oxaspiro[2.5]heptane

E. A. Wetzel, S. Lindeman and W. A. Donaldson

The title compound, C₁₉H₃₀O₂Si, has triclinic (P $\overline{1}$ ) symmetry at 100 K. The O atom of the epoxide group has a pseudoaxial orientation and the dihedral angle between the cyclohexyl and benzene rings is 85.80 (8)°. The C—O—Si—C_t (t = tert-butyl) torsion angle is −177.40 (14)°. In the crystal, pairwise C—H

O links connect the molecules into inversion dimers featuring R²₂(8) loops.

Keywords: crystal structure; organic; spiroepoxide.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S241431462400590X/hb4478sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S241431462400590X/hb4478Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S241431462400590X/hb4478Isup3.cml Supplementary material

CCDC reference: 2363391

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 100 K
R factor = 0.046
wR factor = 0.131
Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.01 Report
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          3 Report
                2-10 12,   2 -1 13,   1 -2 14,

Alert level G
PLAT012_ALERT_1_G No       _shelx_res_checksum Found in CIF ......     Please Check
PLAT063_ALERT_4_G Crystal Size Possibly too Large for Beam Size ..       0.74 mm
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.004 Degree
PLAT398_ALERT_2_G Deviating  C-O-C   Angle From 120 for O2       .       60.4 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         41 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.7 Low
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........      4.399 Note
              Predicted wR2: Based on SigI   2  2.98 or SHELX Weight 11.95       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 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

   4 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

6-[4-(tert-Butyldimethylsilyloxy)phenyl]-1-oxaspiro[2.5]heptane top

Crystal data top

C₁₉H₃₀O₂Si	Z = 2
M_r = 318.52	F(000) = 348
Triclinic, P1	D_x = 1.129 Mg m⁻³
a = 7.3673 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.2285 (4) Å	Cell parameters from 9134 reflections
c = 12.5778 (5) Å	θ = 4.3–70.5°
α = 104.974 (4)°	µ = 1.13 mm⁻¹
β = 101.964 (4)°	T = 100 K
γ = 103.460 (4)°	Plate, colourless
V = 937.09 (7) Å³	0.74 × 0.43 × 0.07 mm

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Cu at home/near, Atlas diffractometer	3539 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	3276 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.046
Detector resolution: 10.3756 pixels mm^-1	θ_max = 70.6°, θ_min = 3.8°
ω scans	h = −8→8
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2018)	k = −13→13
T_min = 0.184, T_max = 1.000	l = −15→15
16772 measured reflections

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0862P)² + 0.2247P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
3539 reflections	Δρ_max = 0.70 e Å⁻³
212 parameters	Δρ_min = −0.35 e Å⁻³
0 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Si1	0.40119 (5)	0.19395 (4)	0.24021 (3)	0.01921 (16)
O1	0.47620 (15)	0.22061 (11)	0.38036 (9)	0.0263 (3)
O2	1.64517 (17)	0.47505 (10)	0.88309 (10)	0.0292 (3)
C1	0.3887 (3)	0.02593 (17)	0.16096 (17)	0.0356 (4)
H1A	0.518022	0.014659	0.180830	0.053*
H1B	0.344470	0.010513	0.078168	0.053*
H1C	0.296937	−0.035756	0.182195	0.053*
C2	0.5762 (2)	0.31022 (18)	0.20005 (16)	0.0315 (4)
H2A	0.556202	0.395409	0.222952	0.047*
H2B	0.555172	0.279906	0.116802	0.047*
H2C	0.709501	0.316690	0.239220	0.047*
C3	0.1549 (2)	0.21993 (14)	0.21951 (13)	0.0220 (3)
C4	0.1760 (2)	0.35451 (16)	0.29980 (15)	0.0290 (4)
H4A	0.228450	0.359582	0.379644	0.044*
H4B	0.048251	0.368942	0.289519	0.044*
H4C	0.264834	0.420774	0.281404	0.044*
C5	0.0722 (2)	0.21241 (16)	0.09442 (15)	0.0287 (4)
H5A	0.156028	0.282682	0.077753	0.043*
H5B	−0.059390	0.220714	0.083054	0.043*
H5C	0.067239	0.129025	0.042720	0.043*
C6	0.0151 (2)	0.11714 (17)	0.24914 (17)	0.0327 (4)
H6A	0.000713	0.030972	0.198313	0.049*
H6B	−0.112221	0.132184	0.238917	0.049*
H6C	0.067749	0.122664	0.329095	0.049*
C7	0.6508 (2)	0.21980 (15)	0.44469 (12)	0.0208 (3)
C8	0.8018 (2)	0.33469 (14)	0.50020 (13)	0.0237 (3)
H8	0.788337	0.412995	0.488878	0.028*
C9	0.9723 (2)	0.33456 (14)	0.57228 (13)	0.0226 (3)
H9	1.075023	0.413377	0.609708	0.027*
C10	0.9962 (2)	0.22092 (14)	0.59095 (12)	0.0196 (3)
C11	0.8430 (2)	0.10703 (14)	0.53377 (13)	0.0212 (3)
H11	0.855594	0.028445	0.544784	0.025*
C12	0.6725 (2)	0.10593 (14)	0.46116 (13)	0.0222 (3)
H12	0.570384	0.027005	0.422645	0.027*
C13	1.1790 (2)	0.22081 (13)	0.67256 (12)	0.0200 (3)
H13	1.167369	0.128847	0.667431	0.024*
C14	1.1985 (2)	0.29503 (15)	0.79754 (13)	0.0228 (3)
H14A	1.206850	0.386201	0.804842	0.027*
H14B	1.080957	0.256789	0.818228	0.027*
C15	1.3792 (2)	0.29093 (15)	0.88093 (13)	0.0230 (3)
H15A	1.394933	0.347476	0.959145	0.028*
H15B	1.361595	0.201524	0.883051	0.028*
C16	1.5596 (2)	0.33507 (13)	0.84517 (13)	0.0214 (3)
C17	1.5456 (2)	0.26890 (15)	0.72234 (13)	0.0232 (3)
H17A	1.539907	0.177436	0.711453	0.028*
H17B	1.663369	0.311268	0.703953	0.028*
C18	1.3644 (2)	0.27461 (14)	0.64068 (13)	0.0225 (3)
H18A	1.352443	0.223818	0.561100	0.027*
H18B	1.378788	0.365426	0.643765	0.027*
C19	1.7490 (2)	0.39772 (16)	0.93104 (15)	0.0285 (4)
H19A	1.865 (3)	0.394 (2)	0.9095 (18)	0.031 (5)*
H19B	1.758 (3)	0.4120 (18)	1.0091 (18)	0.024 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.0177 (2)	0.0210 (2)	0.0203 (3)	0.00703 (16)	0.00510 (16)	0.00808 (17)
O1	0.0212 (5)	0.0382 (6)	0.0223 (6)	0.0115 (5)	0.0069 (4)	0.0116 (5)
O2	0.0337 (6)	0.0184 (5)	0.0308 (6)	0.0041 (4)	0.0067 (5)	0.0055 (4)
C1	0.0330 (9)	0.0308 (9)	0.0370 (10)	0.0150 (7)	0.0022 (7)	0.0023 (7)
C2	0.0219 (8)	0.0424 (9)	0.0390 (10)	0.0118 (7)	0.0103 (7)	0.0245 (8)
C3	0.0176 (7)	0.0226 (7)	0.0274 (8)	0.0061 (5)	0.0066 (6)	0.0105 (6)
C4	0.0250 (8)	0.0288 (8)	0.0356 (9)	0.0123 (6)	0.0108 (7)	0.0089 (7)
C5	0.0227 (8)	0.0300 (8)	0.0316 (9)	0.0079 (6)	0.0020 (6)	0.0114 (7)
C6	0.0223 (8)	0.0334 (9)	0.0483 (11)	0.0068 (6)	0.0133 (7)	0.0220 (8)
C7	0.0196 (7)	0.0285 (7)	0.0164 (7)	0.0093 (6)	0.0062 (5)	0.0082 (6)
C8	0.0279 (8)	0.0219 (7)	0.0247 (8)	0.0096 (6)	0.0083 (6)	0.0105 (6)
C9	0.0226 (7)	0.0199 (7)	0.0234 (8)	0.0034 (5)	0.0053 (6)	0.0072 (6)
C10	0.0213 (7)	0.0212 (7)	0.0179 (7)	0.0072 (5)	0.0082 (6)	0.0064 (6)
C11	0.0242 (7)	0.0186 (7)	0.0226 (7)	0.0071 (5)	0.0089 (6)	0.0072 (6)
C12	0.0217 (7)	0.0220 (7)	0.0201 (7)	0.0032 (5)	0.0070 (6)	0.0043 (6)
C13	0.0211 (7)	0.0194 (7)	0.0206 (7)	0.0069 (5)	0.0066 (6)	0.0071 (6)
C14	0.0231 (7)	0.0267 (7)	0.0216 (8)	0.0092 (6)	0.0090 (6)	0.0090 (6)
C15	0.0252 (8)	0.0254 (7)	0.0200 (7)	0.0082 (6)	0.0072 (6)	0.0088 (6)
C16	0.0237 (7)	0.0183 (7)	0.0225 (8)	0.0072 (5)	0.0053 (6)	0.0073 (6)
C17	0.0209 (7)	0.0249 (7)	0.0230 (8)	0.0072 (6)	0.0073 (6)	0.0054 (6)
C18	0.0219 (7)	0.0270 (7)	0.0183 (7)	0.0065 (6)	0.0075 (6)	0.0063 (6)
C19	0.0250 (8)	0.0306 (8)	0.0254 (9)	0.0058 (6)	0.0040 (6)	0.0068 (7)

Geometric parameters (Å, º) top

Si1—O1	1.6580 (11)	C8—C9	1.389 (2)
Si1—C1	1.8629 (17)	C9—C10	1.399 (2)
Si1—C2	1.8570 (16)	C10—C11	1.394 (2)
Si1—C3	1.8804 (15)	C10—C13	1.515 (2)
O1—C7	1.3735 (18)	C11—C12	1.387 (2)
O2—C16	1.4567 (17)	C13—C14	1.536 (2)
O2—C19	1.446 (2)	C13—C18	1.536 (2)
C3—C4	1.538 (2)	C14—C15	1.533 (2)
C3—C5	1.537 (2)	C15—C16	1.507 (2)
C3—C6	1.536 (2)	C16—C17	1.502 (2)
C7—C8	1.391 (2)	C16—C19	1.461 (2)
C7—C12	1.386 (2)	C17—C18	1.532 (2)

O1—Si1—C1	109.67 (8)	C9—C10—C13	121.75 (13)
O1—Si1—C2	109.22 (7)	C11—C10—C9	117.59 (14)
O1—Si1—C3	103.07 (6)	C11—C10—C13	120.64 (13)
C1—Si1—C3	112.59 (8)	C12—C11—C10	121.44 (14)
C2—Si1—C1	109.20 (9)	C7—C12—C11	120.11 (14)
C2—Si1—C3	112.88 (7)	C10—C13—C14	111.57 (12)
C7—O1—Si1	128.73 (9)	C10—C13—C18	112.72 (12)
C19—O2—C16	60.42 (10)	C18—C13—C14	110.02 (12)
C4—C3—Si1	108.90 (10)	C15—C14—C13	111.77 (12)
C5—C3—Si1	109.90 (10)	C16—C15—C14	111.09 (12)
C5—C3—C4	109.25 (13)	O2—C16—C15	113.99 (12)
C6—C3—Si1	110.17 (10)	O2—C16—C17	114.06 (12)
C6—C3—C4	108.91 (13)	O2—C16—C19	59.43 (10)
C6—C3—C5	109.69 (13)	C17—C16—C15	115.08 (12)
O1—C7—C8	120.15 (13)	C19—C16—C15	120.42 (14)
O1—C7—C12	120.07 (13)	C19—C16—C17	120.66 (13)
C12—C7—C8	119.63 (14)	C16—C17—C18	111.04 (12)
C9—C8—C7	119.77 (14)	C17—C18—C13	111.41 (12)
C8—C9—C10	121.45 (14)	O2—C19—C16	60.15 (10)

O1—Si1—C3—C4	54.6 (1)	C8—C7—C12—C11	0.8 (2)
O1—Si1—C3—C5	174.2 (1)	C7—C12—C11—C10	−0.5 (2)
O1—Si1—C3—C6	−64.8 (1)	C9—C10—C13—C14	66.7 (2)
O1—C7—C8—C9	175.0 (1)	C9—C10—C13—C18	−57.7 (2)
O1—C7—C12—C11	−174.6 (1)	C11—C10—C13—C14	−111.7 (2)
C1—Si1—C3—C4	172.7 (1)	C11—C10—C13—C18	124.0 (2)
C1—Si1—C3—C5	−67.7 (1)	C8—C9—C10—C13	−177.9 (1)
C1—Si1—C3—C6	53.3 (1)	C12—C11—C10—C13	178.2 (1)
C2—Si1—C3—C4	−63.1 (1)	C13—C14—C15—C16	52.9 (2)
C2—Si1—C3—C5	56.5 (1)	C14—C15—C16—C17	−51.4 (2)
C2—Si1—C3—C6	177.5 (1)	C15—C16—C17—C18	52.0 (2)
C1—Si1—O1—C7	62.5 (1)	C16—C17—C18—C13	−54.1 (2)
C2—Si1—O1—C7	−57.2 (1)	C17—C18—C13—C14	56.7 (2)
C3—Si1—O1—C7	−177.40 (14)	C18—C13—C14—C15	−56.2 (2)
Si1—O1—C7—C8	95.0 (2)	O2—C16—C17—C18	−82.4 (2)
Si1—O1—C7—C12	−89.6 (2)	O2—C16—C15—C14	83.1 (2)
C7—C8—C9—C10	−0.2 (2)	C19—C16—C17—C18	−149.9 (1)
C8—C9—C10—C11	0.5 (2)	C19—C16—C15—C14	150.5 (1)
C9—C10—C11—C12	−0.2 (2)	C10—C13—C14—C15	177.9 (1)
C9—C8—C7—C12	−0.5 (2)	C10—C13—C18—C17	−178.07 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2ⁱ	0.99	2.54	3.487 (2)	159

Symmetry code: (i) −x+3, −y+1, −z+2.

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6-[4-(tert-Butyl­dimethyl­sil­yloxy)phen­yl]-1-oxa­spiro­[2.5]hepta­ne

Supporting information

Key indicators

checkCIF/PLATON results

6-[4-(tert-Butyldimethylsilyloxy)phenyl]-1-oxaspiro[2.5]heptane