11,12-Bis(2,2-dimethyl­prop­yl)-9,10-dihydro-9,10-ethenoanthracene

The title compound, C₂₆H₃₂, was retrieved as one of three products from the reaction of tert-butyl­lithium with 11,12-dimethyl­ene-9,10-dihydro­ethenoanthracene and 4,5-diiodo­penta­cyclo­[4.3.0.0^2,4.0^3,8.0^5,7]nonane. The structure shows the expected ethenoanthracene geometry with mol­ecules arranged via van der Waals surfaces.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.048
• wR factor = 0.119
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2002) and XPREP (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: X-SEED; software used to prepare material for publication: X-SEED (Barbour, 2001).

11,12-Bis(2,2-dimethylpropyl)-9,10-dihydro-9,10-ethenoanthracene

Crystal data

C26H32	F(000) = 1504
Mr = 344.52	Dx = 1.080 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7338 reflections
a = 35.531 (7) Å	θ = 2.3–27.8°
b = 12.536 (3) Å	µ = 0.06 mm^−1
c = 9.518 (2) Å	T = 173 K
β = 91.610 (2)°	Transparent plate, colorless
V = 4237.7 (15) Å^3	0.24 × 0.18 × 0.02 mm
Z = 8

Data collection

Bruker SMART APEX CCD diffractometer	3235 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
Graphite monochromator	θmax = 25.4°, θmin = 1.2°
φ and ω scans	h = −42→42
15857 measured reflections	k = −15→15
3878 independent reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0624P)^2 + 1.9402P] where P = (Fo^2 + 2Fc^2)/3
3878 reflections	(Δ/σ)max < 0.001
241 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.19649 (4)	0.93816 (11)	0.46391 (15)	0.0197 (3)
H1	0.1960	1.0030	0.4122	0.024*
C2	0.21532 (4)	0.93253 (12)	0.59407 (15)	0.0213 (3)
H2	0.2274	0.9942	0.6321	0.026*
C3	0.21659 (4)	0.83730 (12)	0.66849 (15)	0.0211 (3)
H3	0.2300	0.8337	0.7561	0.025*
C4	0.19828 (4)	0.74713 (12)	0.61552 (15)	0.0196 (3)
C4A	0.17898 (4)	0.75294 (11)	0.48753 (14)	0.0164 (3)
H4	0.1990	0.6821	0.6668	0.023*
C5	0.19172 (4)	0.55824 (11)	0.21979 (14)	0.0177 (3)
H5	0.1907	0.4938	0.2720	0.021*
C6	0.20903 (4)	0.56057 (12)	0.08928 (15)	0.0194 (3)
H6	0.2196	0.4973	0.0523	0.023*
C7	0.21070 (4)	0.65516 (11)	0.01414 (15)	0.0198 (3)
H7	0.2228	0.6566	−0.0736	0.024*
C8	0.19471 (4)	0.74852 (12)	0.06655 (14)	0.0192 (3)
H8	0.1959	0.8132	0.0148	0.023*
C8A	0.17718 (4)	0.74569 (11)	0.19456 (14)	0.0165 (3)
C9	0.15759 (4)	0.83736 (11)	0.26934 (14)	0.0174 (3)
H9	0.1574	0.9050	0.2137	0.021*
C9A	0.17856 (4)	0.84833 (11)	0.41080 (14)	0.0168 (3)
C10	0.15711 (4)	0.66409 (11)	0.41194 (14)	0.0163 (3)
H10	0.1566	0.5965	0.4676	0.020*
C10A	0.17622 (4)	0.65072 (11)	0.27161 (14)	0.0164 (3)
C11	0.11761 (4)	0.79777 (11)	0.30173 (14)	0.0177 (3)
C12	0.11740 (4)	0.70778 (11)	0.37707 (14)	0.0171 (3)
C13	0.08380 (4)	0.64443 (11)	0.42367 (15)	0.0199 (3)
H13A	0.0889	0.5681	0.4058	0.024*
H13B	0.0619	0.6649	0.3631	0.024*
C14	0.07239 (4)	0.65606 (12)	0.57920 (16)	0.0225 (3)
C15	0.06079 (5)	0.77163 (13)	0.60787 (17)	0.0300 (4)
H15A	0.0399	0.7917	0.5436	0.045*
H15B	0.0823	0.8190	0.5931	0.045*
H15C	0.0528	0.7781	0.7052	0.045*
C16	0.10440 (4)	0.62456 (14)	0.68187 (16)	0.0301 (4)
H16A	0.0955	0.6277	0.7783	0.045*
H16B	0.1255	0.6740	0.6720	0.045*
H16C	0.1127	0.5518	0.6611	0.045*
C17	0.03878 (5)	0.58244 (14)	0.60137 (19)	0.0350 (4)
H17A	0.0462	0.5084	0.5844	0.053*
H17B	0.0182	0.6021	0.5358	0.053*
H17C	0.0304	0.5897	0.6981	0.053*
C18	0.08395 (4)	0.86129 (11)	0.24915 (15)	0.0204 (3)
H18A	0.0895	0.9378	0.2649	0.024*
H18B	0.0623	0.8427	0.3079	0.024*
C19	0.07145 (4)	0.84687 (12)	0.09275 (16)	0.0227 (3)
C20	0.06056 (5)	0.73041 (12)	0.06515 (16)	0.0293 (4)
H20A	0.0404	0.7097	0.1278	0.044*
H20B	0.0825	0.6846	0.0828	0.044*
H20C	0.0518	0.7224	−0.0328	0.044*
C21	0.10255 (5)	0.87942 (14)	−0.00671 (16)	0.0308 (4)
H21A	0.0927	0.8780	−0.1039	0.046*
H21B	0.1237	0.8294	0.0033	0.046*
H21C	0.1112	0.9516	0.0168	0.046*
C22	0.03706 (5)	0.91771 (14)	0.06480 (18)	0.0340 (4)
H22A	0.0438	0.9923	0.0835	0.051*
H22B	0.0168	0.8962	0.1265	0.051*
H22C	0.0286	0.9101	−0.0335	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0216 (8)	0.0174 (7)	0.0201 (7)	−0.0010 (6)	0.0030 (6)	0.0001 (6)
C2	0.0206 (8)	0.0213 (8)	0.0219 (8)	−0.0049 (6)	0.0015 (6)	−0.0047 (6)
C3	0.0207 (8)	0.0270 (8)	0.0154 (7)	−0.0019 (6)	−0.0028 (6)	−0.0008 (6)
C4	0.0209 (7)	0.0198 (7)	0.0180 (7)	−0.0001 (6)	0.0003 (6)	0.0016 (6)
C4A	0.0155 (7)	0.0168 (7)	0.0168 (7)	0.0004 (6)	0.0018 (5)	−0.0014 (6)
C5	0.0174 (7)	0.0170 (7)	0.0186 (7)	−0.0018 (6)	−0.0035 (5)	0.0004 (6)
C6	0.0170 (7)	0.0207 (7)	0.0203 (7)	0.0005 (6)	−0.0019 (6)	−0.0048 (6)
C7	0.0185 (7)	0.0266 (8)	0.0143 (7)	−0.0034 (6)	0.0000 (5)	−0.0026 (6)
C8	0.0204 (8)	0.0210 (7)	0.0160 (7)	−0.0036 (6)	−0.0023 (6)	0.0018 (6)
C8A	0.0155 (7)	0.0177 (7)	0.0162 (7)	−0.0018 (6)	−0.0038 (5)	−0.0008 (6)
C9	0.0205 (7)	0.0158 (7)	0.0157 (7)	0.0000 (6)	−0.0011 (5)	0.0018 (5)
C9A	0.0152 (7)	0.0193 (7)	0.0161 (7)	0.0011 (6)	0.0016 (5)	−0.0013 (6)
C10	0.0184 (7)	0.0150 (7)	0.0155 (7)	−0.0006 (6)	−0.0007 (5)	0.0013 (5)
C10A	0.0133 (7)	0.0189 (7)	0.0169 (7)	−0.0020 (6)	−0.0039 (5)	−0.0010 (6)
C11	0.0202 (7)	0.0176 (7)	0.0151 (7)	0.0003 (6)	−0.0017 (5)	−0.0040 (6)
C12	0.0179 (7)	0.0183 (7)	0.0151 (7)	−0.0001 (6)	−0.0009 (5)	−0.0037 (6)
C13	0.0185 (7)	0.0189 (7)	0.0222 (8)	−0.0005 (6)	−0.0005 (6)	−0.0017 (6)
C14	0.0200 (8)	0.0238 (8)	0.0238 (8)	0.0012 (6)	0.0036 (6)	0.0019 (6)
C15	0.0369 (10)	0.0289 (9)	0.0245 (8)	0.0049 (7)	0.0047 (7)	−0.0021 (7)
C16	0.0275 (9)	0.0408 (10)	0.0221 (8)	0.0043 (7)	0.0052 (6)	0.0091 (7)
C17	0.0274 (9)	0.0377 (10)	0.0406 (10)	−0.0037 (7)	0.0104 (7)	0.0043 (8)
C18	0.0204 (8)	0.0182 (7)	0.0222 (8)	0.0017 (6)	−0.0033 (6)	−0.0011 (6)
C19	0.0219 (8)	0.0224 (8)	0.0234 (8)	0.0012 (6)	−0.0057 (6)	0.0035 (6)
C20	0.0394 (10)	0.0254 (9)	0.0225 (8)	−0.0028 (7)	−0.0082 (7)	−0.0005 (6)
C21	0.0316 (9)	0.0381 (10)	0.0224 (8)	−0.0030 (7)	−0.0070 (7)	0.0081 (7)
C22	0.0297 (9)	0.0337 (9)	0.0377 (10)	0.0055 (7)	−0.0124 (7)	0.0024 (7)

Geometric parameters (Å, º)

C1—C9A	1.383 (2)	C13—C14	1.553 (2)
C1—C2	1.393 (2)	C13—H13A	0.9900
C1—H1	0.9500	C13—H13B	0.9900
C2—C3	1.388 (2)	C14—C17	1.529 (2)
C2—H2	0.9500	C14—C16	1.530 (2)
C3—C4	1.392 (2)	C14—C15	1.533 (2)
C3—H3	0.9500	C15—H15A	0.9800
C4—C4A	1.3829 (19)	C15—H15B	0.9800
C4—H4	0.9500	C15—H15C	0.9800
C4A—C9A	1.401 (2)	C16—H16A	0.9800
C5—C10A	1.3805 (19)	C16—H16B	0.9800
C5—C6	1.402 (2)	C16—H16C	0.9800
C5—H5	0.9500	C17—H17A	0.9800
C6—C7	1.387 (2)	C17—H17B	0.9800
C6—H6	0.9500	C17—H17C	0.9800
C7—C8	1.399 (2)	C18—C19	1.552 (2)
C7—H7	0.9500	C18—H18A	0.9900
C8—C8A	1.3842 (19)	C18—H18B	0.9900
C8—H8	0.9500	C19—C22	1.528 (2)
C8A—C10A	1.3992 (19)	C19—C21	1.531 (2)
C9—C9A	1.5265 (19)	C19—C20	1.531 (2)
C9—C8A	1.5296 (19)	C20—H20A	0.9800
C9—C11	1.544 (2)	C20—H20B	0.9800
C9—H9	1.0000	C20—H20C	0.9800
C10—C10A	1.5245 (19)	C21—H21A	0.9800
C10—C4A	1.5266 (19)	C21—H21B	0.9800
C10—C12	1.5409 (19)	C21—H21C	0.9800
C10—H10	1.0000	C22—H22A	0.9800
C11—C12	1.337 (2)	C22—H22B	0.9800
C11—C18	1.5104 (19)	C22—H22C	0.9800
C12—C13	1.511 (2)
C9A—C1—C2	119.26 (13)	C12—C13—H13B	108.0
C9A—C1—H1	120.4	C14—C13—H13B	108.0
C2—C1—H1	120.4	H13A—C13—H13B	107.2
C3—C2—C1	120.34 (13)	C17—C14—C16	108.99 (13)
C3—C2—H2	119.8	C17—C14—C15	109.33 (13)
C1—C2—H2	119.8	C16—C14—C15	109.20 (13)
C2—C3—C4	120.37 (13)	C17—C14—C13	107.51 (13)
C2—C3—H3	119.8	C16—C14—C13	112.05 (12)
C4—C3—H3	119.8	C15—C14—C13	109.71 (12)
C4A—C4—C3	119.44 (13)	C14—C15—H15A	109.5
C4A—C4—H4	120.3	C14—C15—H15B	109.5
C3—C4—H4	120.3	H15A—C15—H15B	109.5
C4—C4A—C9A	120.12 (13)	C14—C15—H15C	109.5
C4—C4A—C10	127.58 (13)	H15A—C15—H15C	109.5
C9A—C4A—C10	112.29 (12)	H15B—C15—H15C	109.5
C10A—C5—C6	119.24 (13)	C14—C16—H16A	109.5
C10A—C5—H5	120.4	C14—C16—H16B	109.5
C6—C5—H5	120.4	H16A—C16—H16B	109.5
C7—C6—C5	120.06 (13)	C14—C16—H16C	109.5
C7—C6—H6	120.0	H16A—C16—H16C	109.5
C5—C6—H6	120.0	H16B—C16—H16C	109.5
C6—C7—C8	120.51 (13)	C14—C17—H17A	109.5
C6—C7—H7	119.7	C14—C17—H17B	109.5
C8—C7—H7	119.7	H17A—C17—H17B	109.5
C8A—C8—C7	119.32 (13)	C14—C17—H17C	109.5
C8A—C8—H8	120.3	H17A—C17—H17C	109.5
C7—C8—H8	120.3	H17B—C17—H17C	109.5
C8—C8A—C10A	120.08 (13)	C11—C18—C19	117.32 (12)
C8—C8A—C9	127.75 (13)	C11—C18—H18A	108.0
C10A—C8A—C9	112.17 (12)	C19—C18—H18A	108.0
C9A—C9—C8A	105.12 (11)	C11—C18—H18B	108.0
C9A—C9—C11	106.37 (11)	C19—C18—H18B	108.0
C8A—C9—C11	106.53 (11)	H18A—C18—H18B	107.2
C9A—C9—H9	112.7	C22—C19—C21	108.98 (13)
C8A—C9—H9	112.7	C22—C19—C20	109.11 (13)
C11—C9—H9	112.7	C21—C19—C20	109.36 (13)
C1—C9A—C4A	120.43 (13)	C22—C19—C18	107.77 (12)
C1—C9A—C9	127.18 (12)	C21—C19—C18	111.71 (12)
C4A—C9A—C9	112.37 (12)	C20—C19—C18	109.86 (12)
C10A—C10—C4A	105.05 (11)	C19—C20—H20A	109.5
C10A—C10—C12	106.15 (11)	C19—C20—H20B	109.5
C4A—C10—C12	107.04 (11)	H20A—C20—H20B	109.5
C10A—C10—H10	112.7	C19—C20—H20C	109.5
C4A—C10—H10	112.7	H20A—C20—H20C	109.5
C12—C10—H10	112.7	H20B—C20—H20C	109.5
C5—C10A—C8A	120.77 (13)	C19—C21—H21A	109.5
C5—C10A—C10	126.67 (12)	C19—C21—H21B	109.5
C8A—C10A—C10	112.56 (12)	H21A—C21—H21B	109.5
C12—C11—C18	127.32 (13)	C19—C21—H21C	109.5
C12—C11—C9	113.42 (12)	H21A—C21—H21C	109.5
C18—C11—C9	119.25 (12)	H21B—C21—H21C	109.5
C11—C12—C13	128.13 (13)	C19—C22—H22A	109.5
C11—C12—C10	113.36 (12)	C19—C22—H22B	109.5
C13—C12—C10	118.44 (12)	H22A—C22—H22B	109.5
C12—C13—C14	117.40 (12)	C19—C22—H22C	109.5
C12—C13—H13A	108.0	H22A—C22—H22C	109.5
C14—C13—H13A	108.0	H22B—C22—H22C	109.5
C9A—C1—C2—C3	1.1 (2)	C10A—C10—C4A—C4	−120.25 (15)
C1—C2—C3—C4	−1.6 (2)	C12—C10—C4A—C4	127.20 (14)
C2—C3—C4—C4A	0.4 (2)	C10A—C10—C4A—C9A	58.82 (14)
C10A—C5—C6—C7	0.5 (2)	C12—C10—C4A—C9A	−53.74 (15)
C5—C6—C7—C8	−1.0 (2)	C7—C8—C8A—C10A	1.3 (2)
C6—C7—C8—C8A	0.1 (2)	C7—C8—C8A—C9	−179.08 (13)
C9A—C9—C11—C12	−55.47 (15)	C9A—C9—C8A—C8	−121.06 (15)
C8A—C9—C11—C12	56.30 (15)	C11—C9—C8A—C8	126.31 (14)
C9A—C9—C11—C18	124.10 (13)	C9A—C9—C8A—C10A	58.61 (14)
C8A—C9—C11—C18	−124.14 (13)	C11—C9—C8A—C10A	−54.01 (14)
C18—C11—C12—C13	2.7 (2)	C2—C1—C9A—C4A	0.6 (2)
C9—C11—C12—C13	−177.75 (13)	C2—C1—C9A—C9	−178.00 (13)
C18—C11—C12—C10	179.68 (12)	C4—C4A—C9A—C1	−1.8 (2)
C9—C11—C12—C10	−0.80 (16)	C10—C4A—C9A—C1	179.05 (12)
C10A—C10—C12—C11	−55.71 (15)	C4—C4A—C9A—C9	177.02 (12)
C4A—C10—C12—C11	56.09 (15)	C10—C4A—C9A—C9	−2.13 (16)
C10A—C10—C12—C13	121.56 (12)	C8A—C9—C9A—C1	122.51 (15)
C4A—C10—C12—C13	−126.63 (13)	C11—C9—C9A—C1	−124.74 (15)
C11—C12—C13—C14	−102.70 (17)	C8A—C9—C9A—C4A	−56.21 (14)
C10—C12—C13—C14	80.48 (16)	C11—C9—C9A—C4A	56.53 (14)
C12—C13—C14—C17	−178.32 (13)	C6—C5—C10A—C8A	0.9 (2)
C12—C13—C14—C16	−58.59 (17)	C6—C5—C10A—C10	−178.62 (12)
C12—C13—C14—C15	62.88 (17)	C8—C8A—C10A—C5	−1.8 (2)
C12—C11—C18—C19	−100.78 (17)	C9—C8A—C10A—C5	178.50 (12)
C9—C11—C18—C19	79.72 (16)	C8—C8A—C10A—C10	177.80 (12)
C11—C18—C19—C22	179.55 (13)	C9—C8A—C10A—C10	−1.90 (16)
C11—C18—C19—C21	−60.77 (17)	C4A—C10—C10A—C5	123.12 (14)
C11—C18—C19—C20	60.78 (17)	C12—C10—C10A—C5	−123.69 (14)
C3—C4—C4A—C9A	1.3 (2)	C4A—C10—C10A—C8A	−56.45 (14)
C3—C4—C4A—C10	−179.73 (13)	C12—C10—C10A—C8A	56.74 (14)