Triiso­propyl­[5-(4-nitro­phenyl)­tetra­hydro­furan-3-yl­idene­methyl]­silane

Light, M.E.; Hursthouse, M.B.

doi:10.1107/S1600536802001228

Triisopropyl[5-(4-nitrophenyl)tetrahydrofuran-3-ylidenemethyl]silane

M. E. Light and M. B. Hursthouse

In the title compound, C₂₀H₃₁NO₃Si, the nitrophenyl groups of adjacent molecules overlap to form π–π-stacked pairs.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001228/ob6110sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001228/ob6110Isup2.hkl Contains datablock I

CCDC reference: 180810

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.009 Å
R factor = 0.082
wR factor = 0.254
Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.02
         From the CIF: _reflns_number_total               3107
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         3598
         Completeness (_total/calc)             86.35%
          Alert B: < 90% complete (theta max?)


 Alert Level C:



RFACR_01  Alert C The value of the weighted R factor is > 0.25
          Weighted R factor given   0.254

RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.103

PLAT_213  Alert C Atom C14     has ADP max/min Ratio ...........       3.30 prolate

PLAT_213  Alert C Atom C19     has ADP max/min Ratio ...........       3.40 prolate

PLAT_360  Alert C Short  C(sp3)-C(sp3) Bond  C(12)  -   C(14)  =       1.35 Ang.


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 5 Alert Level C = Please check

Computing details top

Data collection: DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO, COLLECT (Hooft, 1998) and maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1998).

Triisopropyl[5-(4-nitrophenyl)tetrahydrofuran-3-ylidenemethyl]silane top

Crystal data top

C₂₀H₃₁NO₃Si	F(000) = 1568
M_r = 361.55	D_x = 1.181 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.6339 (3) Å	Cell parameters from 3107 reflections
b = 7.7463 (1) Å	θ = 3.0–25.0°
c = 35.8752 (7) Å	µ = 0.13 mm⁻¹
β = 91.066 (3)°	T = 120 K
V = 4066.06 (13) Å³	Needle, colourless
Z = 8	0.15 × 0.07 × 0.06 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	3107 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	1445 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.103
Detector resolution: 9.091 pixels/mm pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
Φ and ω scans to fill asymmetric unit	h = −17→17
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	k = −8→8
T_min = 0.980, T_max = 0.992	l = −42→42
6912 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.254	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.13P)²] where P = (F_o² + 2F_c²)/3
3107 reflections	(Δ/σ)_max = 0.002
226 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.5727 (3)	−0.7427 (7)	0.79405 (15)	0.0323 (13)
O1	0.5776 (3)	−0.8886 (5)	0.78142 (11)	0.0428 (12)
O2	0.5447 (3)	−0.7108 (5)	0.82524 (12)	0.0431 (12)
O3	0.7483 (3)	−0.2272 (4)	0.67730 (10)	0.0328 (11)
Si1	0.68995 (13)	0.2141 (2)	0.58388 (5)	0.0375 (6)
C1	0.6186 (4)	−0.2955 (7)	0.76192 (15)	0.0312 (16)
H1	0.6138	−0.1806	0.7709	0.037*
C2	0.5926 (4)	−0.4319 (7)	0.78403 (16)	0.0302 (15)
H2	0.5689	−0.4121	0.8081	0.036*
C3	0.6015 (4)	−0.5961 (7)	0.77061 (16)	0.0263 (14)
C4	0.6352 (4)	−0.6308 (7)	0.73596 (16)	0.0299 (15)
H4	0.6413	−0.7464	0.7275	0.036*
C5	0.6600 (4)	−0.4950 (7)	0.71375 (16)	0.0312 (16)
H5	0.6829	−0.5166	0.6896	0.037*
C6	0.6519 (4)	−0.3257 (7)	0.72634 (16)	0.0282 (15)
C7	0.6765 (4)	−0.1750 (7)	0.70137 (16)	0.0304 (15)
H7	0.6980	−0.0761	0.7172	0.036*
C8	0.6009 (4)	−0.1134 (7)	0.67492 (15)	0.0338 (16)
H8A	0.5650	−0.2114	0.6647	0.041*
H8B	0.5593	−0.0318	0.6874	0.041*
C9	0.6551 (4)	−0.0245 (7)	0.64485 (15)	0.0276 (15)
C10	0.7487 (4)	−0.1048 (7)	0.64699 (16)	0.0351 (16)
H10A	0.7624	−0.1640	0.6233	0.042*
H10B	0.7957	−0.0151	0.6516	0.042*
C11	0.6272 (4)	0.0973 (8)	0.62150 (15)	0.0369 (16)
H11	0.5653	0.1314	0.6242	0.044*
C12	0.6177 (5)	0.4071 (8)	0.57111 (18)	0.057 (2)
H12	0.6611	0.4795	0.5566	0.068*
C13	0.5966 (5)	0.5234 (8)	0.60428 (17)	0.053 (2)
H13A	0.6523	0.5407	0.6194	0.079*
H13B	0.5497	0.4689	0.6195	0.079*
H13C	0.5742	0.6353	0.5952	0.079*
C14	0.5464 (10)	0.3907 (15)	0.5471 (3)	0.216 (9)
H14A	0.5639	0.3168	0.5262	0.324*
H14B	0.5287	0.5048	0.5377	0.324*
H14C	0.4947	0.3385	0.5600	0.324*
C15	0.8096 (4)	0.2760 (8)	0.59925 (16)	0.0422 (18)
H15	0.8457	0.1665	0.6004	0.051*
C16	0.8196 (4)	0.3606 (7)	0.63799 (16)	0.0437 (18)
H16A	0.7913	0.2865	0.6567	0.066*
H16B	0.7893	0.4734	0.6377	0.066*
H16C	0.8846	0.3758	0.6443	0.066*
C17	0.8567 (5)	0.3929 (10)	0.57045 (18)	0.066 (2)
H17A	0.8516	0.3400	0.5457	0.099*
H17B	0.9213	0.4067	0.5774	0.099*
H17C	0.8269	0.5063	0.5700	0.099*
C18	0.6989 (5)	0.0710 (8)	0.54094 (16)	0.0448 (18)
H18	0.7060	0.1500	0.5191	0.054*
C19	0.7813 (7)	−0.0489 (13)	0.5413 (2)	0.139 (5)
H19A	0.8371	0.0186	0.5458	0.209*
H19B	0.7850	−0.1078	0.5172	0.209*
H19C	0.7749	−0.1346	0.5612	0.209*
C20	0.6128 (6)	−0.0332 (10)	0.53349 (19)	0.078 (3)
H20A	0.5598	0.0441	0.5329	0.118*
H20B	0.6056	−0.1187	0.5534	0.118*
H20C	0.6175	−0.0925	0.5095	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.016 (3)	0.039 (3)	0.042 (3)	0.002 (3)	0.001 (3)	−0.002 (3)
O1	0.044 (3)	0.034 (3)	0.051 (3)	−0.006 (2)	0.001 (2)	0.001 (2)
O2	0.034 (3)	0.048 (3)	0.048 (3)	−0.001 (2)	0.011 (2)	0.003 (2)
O3	0.023 (3)	0.033 (2)	0.043 (3)	0.004 (2)	0.006 (2)	0.0083 (19)
Si1	0.0382 (13)	0.0451 (11)	0.0295 (10)	0.0058 (9)	0.0051 (9)	0.0031 (8)
C1	0.032 (4)	0.025 (3)	0.036 (4)	0.008 (3)	−0.004 (3)	−0.002 (3)
C2	0.025 (4)	0.031 (4)	0.035 (4)	0.003 (3)	0.003 (3)	−0.003 (3)
C3	0.027 (4)	0.018 (3)	0.034 (4)	−0.001 (3)	0.001 (3)	0.003 (3)
C4	0.021 (4)	0.028 (3)	0.040 (4)	0.005 (3)	−0.005 (3)	0.002 (3)
C5	0.029 (4)	0.033 (4)	0.031 (4)	0.004 (3)	−0.001 (3)	−0.002 (3)
C6	0.013 (4)	0.034 (4)	0.037 (4)	−0.001 (3)	−0.004 (3)	0.000 (3)
C7	0.020 (4)	0.032 (3)	0.039 (4)	0.000 (3)	0.004 (3)	−0.002 (3)
C8	0.019 (4)	0.043 (4)	0.040 (4)	0.007 (3)	0.005 (3)	−0.004 (3)
C9	0.019 (4)	0.031 (3)	0.033 (4)	0.000 (3)	0.005 (3)	−0.004 (3)
C10	0.027 (4)	0.032 (4)	0.046 (4)	0.003 (3)	0.004 (3)	0.012 (3)
C11	0.028 (4)	0.046 (4)	0.037 (4)	0.007 (3)	0.000 (3)	−0.002 (3)
C12	0.075 (6)	0.061 (5)	0.034 (4)	0.025 (4)	−0.006 (4)	0.010 (4)
C13	0.063 (6)	0.048 (4)	0.047 (4)	0.013 (4)	0.005 (4)	0.007 (3)
C14	0.33 (2)	0.188 (12)	0.122 (9)	0.184 (14)	−0.142 (12)	−0.090 (9)
C15	0.045 (5)	0.044 (4)	0.038 (4)	0.001 (4)	0.006 (3)	0.003 (3)
C16	0.045 (5)	0.045 (4)	0.042 (4)	−0.002 (4)	0.003 (3)	0.005 (3)
C17	0.036 (5)	0.110 (6)	0.053 (5)	−0.017 (5)	0.008 (4)	0.020 (4)
C18	0.056 (5)	0.048 (4)	0.031 (4)	−0.003 (4)	0.005 (4)	0.000 (3)
C19	0.170 (11)	0.162 (10)	0.085 (7)	0.115 (9)	−0.033 (7)	−0.073 (7)
C20	0.104 (8)	0.076 (5)	0.057 (5)	−0.034 (5)	0.032 (5)	−0.019 (4)

Geometric parameters (Å, º) top

N1—O1	1.220 (5)	C11—H11	0.9500
N1—O2	1.224 (6)	C12—C14	1.346 (11)
N1—C3	1.479 (7)	C12—C13	1.529 (8)
O3—C7	1.432 (6)	C12—H12	1.0000
O3—C10	1.443 (6)	C13—H13A	0.9800
Si1—C11	1.879 (6)	C13—H13B	0.9800
Si1—C12	1.882 (7)	C13—H13C	0.9800
Si1—C15	1.888 (7)	C14—H14A	0.9800
Si1—C18	1.904 (6)	C14—H14B	0.9800
C1—C2	1.379 (7)	C14—H14C	0.9800
C1—C6	1.395 (7)	C15—C16	1.541 (8)
C1—H1	0.9500	C15—C17	1.545 (8)
C2—C3	1.367 (7)	C15—H15	1.0000
C2—H2	0.9500	C16—H16A	0.9800
C3—C4	1.372 (7)	C16—H16B	0.9800
C4—C5	1.372 (7)	C16—H16C	0.9800
C4—H4	0.9500	C17—H17A	0.9800
C5—C6	1.392 (7)	C17—H17B	0.9800
C5—H5	0.9500	C17—H17C	0.9800
C6—C7	1.518 (8)	C18—C20	1.516 (9)
C7—C8	1.521 (8)	C18—C19	1.522 (9)
C7—H7	1.0000	C18—H18	1.0000
C8—C9	1.517 (7)	C19—H19A	0.9800
C8—H8A	0.9900	C19—H19B	0.9800
C8—H8B	0.9900	C19—H19C	0.9800
C9—C11	1.322 (7)	C20—H20A	0.9800
C9—C10	1.504 (7)	C20—H20B	0.9800
C10—H10A	0.9900	C20—H20C	0.9800
C10—H10B	0.9900

O1—N1—O2	123.3 (5)	C14—C12—Si1	120.4 (7)
O1—N1—C3	118.7 (5)	C13—C12—Si1	113.6 (4)
O2—N1—C3	118.0 (5)	C14—C12—H12	102.3
C7—O3—C10	106.4 (4)	C13—C12—H12	102.3
C11—Si1—C12	106.1 (3)	Si1—C12—H12	102.3
C11—Si1—C15	112.1 (3)	C12—C13—H13A	109.5
C12—Si1—C15	112.5 (3)	C12—C13—H13B	109.5
C11—Si1—C18	110.1 (3)	H13A—C13—H13B	109.5
C12—Si1—C18	108.2 (3)	C12—C13—H13C	109.5
C15—Si1—C18	107.9 (3)	H13A—C13—H13C	109.5
C2—C1—C6	120.2 (5)	H13B—C13—H13C	109.5
C2—C1—H1	119.9	C12—C14—H14A	109.5
C6—C1—H1	119.9	C12—C14—H14B	109.5
C3—C2—C1	118.8 (5)	H14A—C14—H14B	109.5
C3—C2—H2	120.6	C12—C14—H14C	109.5
C1—C2—H2	120.6	H14A—C14—H14C	109.5
C2—C3—C4	122.6 (5)	H14B—C14—H14C	109.5
C2—C3—N1	118.9 (5)	C16—C15—C17	108.5 (5)
C4—C3—N1	118.4 (5)	C16—C15—Si1	116.3 (4)
C3—C4—C5	118.6 (5)	C17—C15—Si1	112.1 (4)
C3—C4—H4	120.7	C16—C15—H15	106.4
C5—C4—H4	120.7	C17—C15—H15	106.4
C4—C5—C6	120.6 (5)	Si1—C15—H15	106.4
C4—C5—H5	119.7	C15—C16—H16A	109.5
C6—C5—H5	119.7	C15—C16—H16B	109.5
C5—C6—C1	119.2 (5)	H16A—C16—H16B	109.5
C5—C6—C7	120.7 (5)	C15—C16—H16C	109.5
C1—C6—C7	120.1 (5)	H16A—C16—H16C	109.5
O3—C7—C6	108.8 (4)	H16B—C16—H16C	109.5
O3—C7—C8	104.2 (4)	C15—C17—H17A	109.5
C6—C7—C8	115.6 (5)	C15—C17—H17B	109.5
O3—C7—H7	109.3	H17A—C17—H17B	109.5
C6—C7—H7	109.3	C15—C17—H17C	109.5
C8—C7—H7	109.3	H17A—C17—H17C	109.5
C9—C8—C7	101.7 (5)	H17B—C17—H17C	109.5
C9—C8—H8A	111.4	C20—C18—C19	109.4 (7)
C7—C8—H8A	111.4	C20—C18—Si1	112.5 (5)
C9—C8—H8B	111.4	C19—C18—Si1	114.5 (5)
C7—C8—H8B	111.4	C20—C18—H18	106.6
H8A—C8—H8B	109.3	C19—C18—H18	106.6
C11—C9—C10	126.8 (5)	Si1—C18—H18	106.6
C11—C9—C8	127.9 (6)	C18—C19—H19A	109.5
C10—C9—C8	105.3 (5)	C18—C19—H19B	109.5
O3—C10—C9	107.1 (5)	H19A—C19—H19B	109.5
O3—C10—H10A	110.3	C18—C19—H19C	109.5
C9—C10—H10A	110.3	H19A—C19—H19C	109.5
O3—C10—H10B	110.3	H19B—C19—H19C	109.5
C9—C10—H10B	110.3	C18—C20—H20A	109.5
H10A—C10—H10B	108.6	C18—C20—H20B	109.5
C9—C11—Si1	130.5 (5)	H20A—C20—H20B	109.5
C9—C11—H11	114.8	C18—C20—H20C	109.5
Si1—C11—H11	114.8	H20A—C20—H20C	109.5
C14—C12—C13	112.8 (7)	H20B—C20—H20C	109.5

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Triiso­propyl­[5-(4-nitro­phenyl)­tetra­hydro­furan-3-yl­idene­methyl]­silane

Supporting information

Key indicators

checkCIF results

Triisopropyl[5-(4-nitrophenyl)tetrahydrofuran-3-ylidenemethyl]silane