6-[(tert-Butyl­dimethyl­sil­yl)­oxy]-3-ethenyl-7-meth­oxy-4-[(tri­methyl­sil­yl)ethyn­yl]naphtho­[2,3-c]furan-1(3H)-one

The tricyclic core in the title compound, C₂₆H₃₄O₄Si₂, shows disorder of the furan ring and deviates slightly from planarity, with the largest displacement from the least-squares plane [0.166 (2) Å] for the major disordered part of the methine C atom. To this C atom the likewise disordered vinyl group is attached, lying nearly perpendicular to the tricyclic core. In the crystal, mutual C—H...π inter­actions between the methine group of the furan ring and the central ring of the tricyclic core of an adjacent mol­ecule lead to inversion-related dimers.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.041
• wR factor = 0.104
• Data-to-parameter ratio = 19.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C High   MainMol Ueq as Compared to Neighbors of        C14 Check

Alert level G
PLAT230_ALERT_2_G Hirshfeld Test Diff for    Si1      --C16      .        6.9 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for    O1       --C1       .        6.0 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         9% Note
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C10      - C15      .       1.43 Ang.
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O3             130.7 Degree
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: XP (Sheldrick, 2008) and Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

6-[(tert-Butyldimethylsilyl)oxy]-3-ethenyl-7-methoxy-4-[(trimethylsilyl)ethynyl]naphtho[2,3-c]furan-1(3H)-one

Crystal data

C26H34O4Si2	F(000) = 1000
Mr = 466.71	Dx = 1.180 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.2628 (6) Å	Cell parameters from 8947 reflections
b = 20.5653 (13) Å	θ = 2.4–28.1°
c = 13.3923 (8) Å	µ = 0.16 mm^−1
β = 111.6378 (15)°	T = 100 K
V = 2627.4 (3) Å^3	Block, colourless
Z = 4	0.20 × 0.20 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer	4923 reflections with I > 2σ(I)
ω– and φ–scans	Rint = 0.038
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θmax = 28.0°, θmin = 2.4°
Tmin = 0.691, Tmax = 0.746	h = −13→13
29229 measured reflections	k = −27→27
6339 independent reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0483P)^2 + 1.0291P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
6339 reflections	Δρmax = 0.42 e Å^−3
326 parameters	Δρmin = −0.24 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	0.20791 (5)	0.30679 (2)	0.57403 (3)	0.02248 (11)
C1	0.7133 (2)	0.48696 (8)	0.37326 (13)	0.0302 (4)
Si2	0.67617 (4)	0.34083 (2)	0.98331 (3)	0.01647 (10)
O2	0.79449 (14)	0.51514 (6)	0.34281 (9)	0.0338 (3)
C2	0.73267 (18)	0.46099 (7)	0.48068 (12)	0.0231 (3)
O3	0.81087 (11)	0.36239 (6)	0.94866 (8)	0.0237 (2)
C3	0.84777 (17)	0.46481 (7)	0.57425 (13)	0.0217 (3)
H3	0.931227	0.485539	0.575825	0.026*
O4	1.03876 (11)	0.42083 (5)	0.96159 (9)	0.0237 (2)
C4	0.83931 (16)	0.43714 (7)	0.66845 (12)	0.0184 (3)
C5	0.95276 (16)	0.44210 (7)	0.76950 (12)	0.0206 (3)
H5	1.037576	0.462529	0.773525	0.025*
C6	0.94047 (16)	0.41766 (7)	0.86068 (12)	0.0193 (3)
C7	0.81345 (16)	0.38558 (7)	0.85467 (11)	0.0183 (3)
C8	0.70463 (16)	0.37984 (7)	0.75858 (12)	0.0181 (3)
H8	0.621620	0.358099	0.755637	0.022*
C9	0.71283 (16)	0.40565 (7)	0.66304 (11)	0.0168 (3)
C10	0.59432 (17)	0.40258 (7)	0.56348 (12)	0.0203 (3)
C11	0.60720 (18)	0.43166 (8)	0.47435 (12)	0.0256 (4)
C14	0.2766 (2)	0.38807 (11)	0.27074 (15)	0.0403 (5)
H14A	0.228359	0.423527	0.286908	0.048*	0.793 (5)
H14B	0.225496	0.351833	0.231592	0.048*	0.793 (5)
H14C	0.299781	0.344558	0.260154	0.048*	0.207 (5)
H14D	0.181140	0.401044	0.247364	0.048*	0.207 (5)
C15	0.46697 (17)	0.37325 (8)	0.56158 (12)	0.0230 (3)
C16	0.36373 (18)	0.34782 (8)	0.56664 (12)	0.0260 (4)
C17	0.0501 (2)	0.34828 (10)	0.47995 (15)	0.0389 (5)
H17A	0.048349	0.393362	0.503155	0.058*
H17B	−0.034178	0.325613	0.479467	0.058*
H17C	0.052507	0.347805	0.407497	0.058*
C18	0.2142 (2)	0.22140 (9)	0.53083 (16)	0.0364 (4)
H18A	0.214109	0.220951	0.457613	0.055*
H18B	0.132165	0.197743	0.532449	0.055*
H18C	0.299819	0.200466	0.579619	0.055*
C19	0.21649 (19)	0.31364 (9)	0.71450 (13)	0.0318 (4)
H19A	0.295737	0.288043	0.761874	0.048*
H19B	0.129237	0.297148	0.719013	0.048*
H19C	0.229034	0.359329	0.736794	0.048*
C20	0.54271 (18)	0.40670 (8)	0.94724 (13)	0.0282 (4)
H20A	0.584916	0.446626	0.985485	0.042*
H20B	0.464002	0.393737	0.967605	0.042*
H20C	0.508864	0.414466	0.869624	0.042*
C21	0.59902 (19)	0.26318 (8)	0.91747 (13)	0.0282 (4)
H21A	0.555877	0.269748	0.839637	0.042*
H21B	0.527592	0.248566	0.944850	0.042*
H21C	0.672816	0.230206	0.933128	0.042*
C22	0.6523 (2)	0.31159 (11)	1.17885 (15)	0.0403 (5)
H22A	0.606496	0.270853	1.146464	0.060*
H22B	0.582055	0.346268	1.163324	0.060*
H22C	0.697512	0.306043	1.256777	0.060*
C23	0.76275 (17)	0.32974 (8)	1.13195 (12)	0.0214 (3)
C24	0.87241 (19)	0.27524 (9)	1.15756 (14)	0.0316 (4)
H24A	0.943282	0.286281	1.127394	0.047*
H24B	0.826462	0.234372	1.126024	0.047*
H24C	0.917511	0.270285	1.235607	0.047*
C25	0.8359 (2)	0.39328 (9)	1.18330 (14)	0.0378 (5)
H25A	0.878708	0.387841	1.261393	0.057*
H25B	0.766840	0.428533	1.166339	0.057*
H25C	0.908657	0.403970	1.154917	0.057*
C26	1.16625 (17)	0.45412 (9)	0.97460 (14)	0.0316 (4)
H26A	1.210789	0.433590	0.929264	0.047*
H26B	1.229676	0.451859	1.049976	0.047*
H26C	1.145690	0.499728	0.953463	0.047*
O1	0.5726 (3)	0.47723 (11)	0.30613 (17)	0.0254 (5)	0.793 (5)
C12	0.4924 (3)	0.44639 (12)	0.36387 (16)	0.0206 (5)	0.793 (5)
H12	0.424850	0.478621	0.373199	0.025*	0.793 (5)
C13	0.4132 (2)	0.38915 (10)	0.30236 (14)	0.0227 (6)	0.793 (5)
H13	0.461811	0.353786	0.286346	0.027*	0.793 (5)
O1'	0.6138 (9)	0.4537 (4)	0.3060 (6)	0.0201 (16)	0.207 (5)
C12'	0.5382 (9)	0.4140 (4)	0.3596 (6)	0.018 (2)	0.207 (5)
H12'	0.543941	0.366360	0.346803	0.022*	0.207 (5)
C13'	0.3928 (10)	0.4372 (4)	0.3254 (6)	0.023 (2)	0.207 (5)
H13'	0.371872	0.480928	0.336729	0.028*	0.207 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0213 (2)	0.0254 (2)	0.0191 (2)	−0.00752 (18)	0.00542 (17)	−0.00023 (17)
C1	0.0448 (11)	0.0291 (9)	0.0220 (8)	−0.0110 (8)	0.0187 (8)	−0.0028 (7)
Si2	0.0167 (2)	0.0190 (2)	0.01550 (19)	−0.00173 (16)	0.00805 (16)	−0.00036 (15)
O2	0.0491 (8)	0.0330 (7)	0.0283 (6)	−0.0114 (6)	0.0250 (6)	0.0016 (5)
C2	0.0345 (9)	0.0204 (8)	0.0206 (8)	−0.0043 (7)	0.0175 (7)	−0.0002 (6)
O3	0.0188 (6)	0.0348 (6)	0.0182 (5)	−0.0029 (5)	0.0077 (4)	0.0081 (5)
C3	0.0254 (8)	0.0190 (7)	0.0273 (8)	−0.0009 (6)	0.0176 (7)	0.0015 (6)
O4	0.0158 (5)	0.0290 (6)	0.0247 (6)	−0.0021 (4)	0.0058 (4)	0.0078 (5)
C4	0.0225 (8)	0.0158 (7)	0.0222 (7)	0.0009 (6)	0.0145 (6)	0.0011 (6)
C5	0.0173 (7)	0.0197 (7)	0.0280 (8)	0.0004 (6)	0.0119 (6)	0.0041 (6)
C6	0.0167 (7)	0.0185 (7)	0.0235 (7)	0.0031 (6)	0.0082 (6)	0.0036 (6)
C7	0.0199 (7)	0.0196 (7)	0.0189 (7)	0.0017 (6)	0.0113 (6)	0.0043 (6)
C8	0.0197 (7)	0.0185 (7)	0.0198 (7)	−0.0026 (6)	0.0116 (6)	0.0006 (6)
C9	0.0216 (8)	0.0144 (6)	0.0186 (7)	0.0004 (6)	0.0124 (6)	−0.0006 (5)
C10	0.0283 (8)	0.0183 (7)	0.0182 (7)	−0.0051 (6)	0.0129 (6)	−0.0022 (6)
C11	0.0351 (10)	0.0261 (8)	0.0175 (7)	−0.0088 (7)	0.0118 (7)	−0.0030 (6)
C14	0.0319 (10)	0.0516 (12)	0.0354 (10)	0.0004 (9)	0.0103 (8)	−0.0008 (9)
C15	0.0316 (9)	0.0249 (8)	0.0125 (7)	−0.0071 (7)	0.0081 (6)	−0.0014 (6)
C16	0.0310 (9)	0.0302 (9)	0.0160 (7)	−0.0090 (7)	0.0078 (7)	−0.0001 (6)
C17	0.0307 (10)	0.0473 (12)	0.0315 (10)	0.0019 (9)	0.0030 (8)	0.0040 (8)
C18	0.0412 (11)	0.0298 (9)	0.0421 (11)	−0.0103 (8)	0.0199 (9)	−0.0053 (8)
C19	0.0276 (9)	0.0456 (11)	0.0222 (8)	−0.0134 (8)	0.0092 (7)	0.0010 (7)
C20	0.0246 (9)	0.0318 (9)	0.0262 (8)	0.0051 (7)	0.0068 (7)	0.0001 (7)
C21	0.0359 (10)	0.0259 (8)	0.0241 (8)	−0.0076 (7)	0.0126 (7)	−0.0044 (7)
C22	0.0421 (11)	0.0612 (13)	0.0272 (9)	0.0061 (10)	0.0239 (9)	0.0098 (9)
C23	0.0260 (8)	0.0239 (8)	0.0164 (7)	0.0010 (6)	0.0104 (6)	0.0017 (6)
C24	0.0342 (10)	0.0336 (9)	0.0274 (9)	0.0094 (8)	0.0118 (8)	0.0089 (7)
C25	0.0518 (12)	0.0310 (10)	0.0190 (8)	−0.0006 (9)	−0.0004 (8)	−0.0029 (7)
C26	0.0177 (8)	0.0393 (10)	0.0333 (9)	−0.0071 (7)	0.0041 (7)	0.0079 (8)
O1	0.0336 (13)	0.0260 (11)	0.0198 (8)	−0.0034 (8)	0.0135 (8)	0.0048 (8)
C12	0.0278 (14)	0.0183 (11)	0.0186 (10)	0.0009 (10)	0.0119 (10)	0.0021 (8)
C13	0.0338 (13)	0.0223 (11)	0.0141 (9)	0.0017 (8)	0.0113 (9)	0.0005 (8)
O1'	0.023 (4)	0.029 (4)	0.016 (3)	−0.004 (3)	0.016 (3)	0.002 (3)
C12'	0.028 (5)	0.015 (4)	0.018 (4)	0.002 (3)	0.016 (3)	0.006 (3)
C13'	0.029 (5)	0.020 (4)	0.022 (4)	0.002 (3)	0.011 (4)	0.001 (3)

Geometric parameters (Å, º)

Si1—C16	1.8427 (17)	C17—H17A	0.9800
Si1—C17	1.8533 (19)	C17—H17B	0.9800
Si1—C19	1.8559 (17)	C17—H17C	0.9800
Si1—C18	1.8575 (19)	C18—H18A	0.9800
C1—O2	1.203 (2)	C18—H18B	0.9800
C1—O1'	1.282 (8)	C18—H18C	0.9800
C1—O1	1.405 (3)	C19—H19A	0.9800
C1—C2	1.478 (2)	C19—H19B	0.9800
Si2—O3	1.6721 (11)	C19—H19C	0.9800
Si2—C21	1.8546 (17)	C20—H20A	0.9800
Si2—C20	1.8592 (17)	C20—H20B	0.9800
Si2—C23	1.8708 (15)	C20—H20C	0.9800
C2—C3	1.371 (2)	C21—H21A	0.9800
C2—C11	1.396 (2)	C21—H21B	0.9800
O3—C7	1.3554 (17)	C21—H21C	0.9800
C3—C4	1.415 (2)	C22—C23	1.531 (2)
C3—H3	0.9500	C22—H22A	0.9800
O4—C6	1.3574 (18)	C22—H22B	0.9800
O4—C26	1.4293 (19)	C22—H22C	0.9800
C4—C5	1.427 (2)	C23—C24	1.535 (2)
C4—C9	1.428 (2)	C23—C25	1.537 (2)
C5—C6	1.369 (2)	C24—H24A	0.9800
C5—H5	0.9500	C24—H24B	0.9800
C6—C7	1.437 (2)	C24—H24C	0.9800
C7—C8	1.363 (2)	C25—H25A	0.9800
C8—C9	1.4162 (19)	C25—H25B	0.9800
C8—H8	0.9500	C25—H25C	0.9800
C9—C10	1.437 (2)	C26—H26A	0.9800
C10—C11	1.384 (2)	C26—H26B	0.9800
C10—C15	1.431 (2)	C26—H26C	0.9800
C11—C12'	1.481 (8)	O1—C12	1.465 (3)
C11—C12	1.544 (3)	C12—C13	1.494 (3)
C14—C13	1.307 (3)	C12—H12	1.0000
C14—C13'	1.528 (9)	C13—H13	0.9500
C14—H14A	0.9500	O1'—C12'	1.481 (10)
C14—H14B	0.9500	C12'—C13'	1.470 (13)
C14—H14C	0.9500	C12'—H12'	1.0000
C14—H14D	0.9500	C13'—H13'	0.9500
C15—C16	1.206 (2)
C16—Si1—C17	108.12 (9)	H18B—C18—H18C	109.5
C16—Si1—C19	107.58 (7)	Si1—C19—H19A	109.5
C17—Si1—C19	110.92 (9)	Si1—C19—H19B	109.5
C16—Si1—C18	106.58 (8)	H19A—C19—H19B	109.5
C17—Si1—C18	110.23 (9)	Si1—C19—H19C	109.5
C19—Si1—C18	113.17 (9)	H19A—C19—H19C	109.5
O2—C1—O1'	119.4 (3)	H19B—C19—H19C	109.5
O2—C1—O1	121.90 (16)	Si2—C20—H20A	109.5
O2—C1—C2	129.99 (17)	Si2—C20—H20B	109.5
O1'—C1—C2	106.1 (4)	H20A—C20—H20B	109.5
O1—C1—C2	108.01 (15)	Si2—C20—H20C	109.5
O3—Si2—C21	110.37 (7)	H20A—C20—H20C	109.5
O3—Si2—C20	109.88 (7)	H20B—C20—H20C	109.5
C21—Si2—C20	111.06 (8)	Si2—C21—H21A	109.5
O3—Si2—C23	102.17 (6)	Si2—C21—H21B	109.5
C21—Si2—C23	110.66 (7)	H21A—C21—H21B	109.5
C20—Si2—C23	112.38 (7)	Si2—C21—H21C	109.5
C3—C2—C11	123.00 (14)	H21A—C21—H21C	109.5
C3—C2—C1	129.09 (15)	H21B—C21—H21C	109.5
C11—C2—C1	107.88 (14)	C23—C22—H22A	109.5
C7—O3—Si2	130.71 (10)	C23—C22—H22B	109.5
C2—C3—C4	118.44 (14)	H22A—C22—H22B	109.5
C2—C3—H3	120.8	C23—C22—H22C	109.5
C4—C3—H3	120.8	H22A—C22—H22C	109.5
C6—O4—C26	117.07 (12)	H22B—C22—H22C	109.5
C3—C4—C5	121.33 (14)	C22—C23—C24	108.86 (14)
C3—C4—C9	119.35 (14)	C22—C23—C25	109.68 (15)
C5—C4—C9	119.28 (13)	C24—C23—C25	108.91 (15)
C6—C5—C4	120.57 (14)	C22—C23—Si2	109.46 (12)
C6—C5—H5	119.7	C24—C23—Si2	110.38 (11)
C4—C5—H5	119.7	C25—C23—Si2	109.53 (11)
O4—C6—C5	126.26 (14)	C23—C24—H24A	109.5
O4—C6—C7	113.81 (13)	C23—C24—H24B	109.5
C5—C6—C7	119.92 (14)	H24A—C24—H24B	109.5
O3—C7—C8	123.82 (13)	C23—C24—H24C	109.5
O3—C7—C6	115.95 (13)	H24A—C24—H24C	109.5
C8—C7—C6	120.23 (13)	H24B—C24—H24C	109.5
C7—C8—C9	121.31 (14)	C23—C25—H25A	109.5
C7—C8—H8	119.3	C23—C25—H25B	109.5
C9—C8—H8	119.3	H25A—C25—H25B	109.5
C8—C9—C4	118.67 (13)	C23—C25—H25C	109.5
C8—C9—C10	120.66 (13)	H25A—C25—H25C	109.5
C4—C9—C10	120.63 (13)	H25B—C25—H25C	109.5
C11—C10—C15	122.94 (14)	O4—C26—H26A	109.5
C11—C10—C9	117.63 (14)	O4—C26—H26B	109.5
C15—C10—C9	119.34 (13)	H26A—C26—H26B	109.5
C10—C11—C2	120.90 (15)	O4—C26—H26C	109.5
C10—C11—C12'	128.9 (3)	H26A—C26—H26C	109.5
C2—C11—C12'	104.3 (3)	H26B—C26—H26C	109.5
C10—C11—C12	129.02 (16)	C1—O1—C12	111.62 (18)
C2—C11—C12	109.51 (14)	O1—C12—C13	110.33 (17)
C13—C14—H14A	120.0	O1—C12—C11	102.26 (18)
C13—C14—H14B	120.0	C13—C12—C11	116.20 (18)
H14A—C14—H14B	120.0	O1—C12—H12	109.2
C13'—C14—H14C	120.0	C13—C12—H12	109.2
C13'—C14—H14D	120.0	C11—C12—H12	109.2
H14C—C14—H14D	120.0	C14—C13—C12	119.5 (2)
C16—C15—C10	175.98 (16)	C14—C13—H13	120.2
C15—C16—Si1	178.46 (16)	C12—C13—H13	120.2
Si1—C17—H17A	109.5	C1—O1'—C12'	112.2 (6)
Si1—C17—H17B	109.5	C13'—C12'—O1'	108.9 (7)
H17A—C17—H17B	109.5	C13'—C12'—C11	106.6 (7)
Si1—C17—H17C	109.5	O1'—C12'—C11	103.4 (6)
H17A—C17—H17C	109.5	C13'—C12'—H12'	112.5
H17B—C17—H17C	109.5	O1'—C12'—H12'	112.5
Si1—C18—H18A	109.5	C11—C12'—H12'	112.5
Si1—C18—H18B	109.5	C12'—C13'—C14	117.3 (6)
H18A—C18—H18B	109.5	C12'—C13'—H13'	121.4
Si1—C18—H18C	109.5	C14—C13'—H13'	121.4
H18A—C18—H18C	109.5