9-Phenyl-3,4,4a,9a-tetrahydrotri­ptycene and 9-phenyl-1,2,3,4,4a,9a-hexa­hydro­triptycene

The structure of 9-phenyl-3,4,4a,9a-tetra­hydro­triptycene, C₂₆H₂₂, (I), exhibits regiochemistry consistent with a stepwise mechanism for its formation from photo­cyclo­addition of 1,3-cyclo­hexa­diene and 9-phenyl­anthracene. Bond distances involving the bridgehead C atoms are similar in (I) and the hydrogenated derivative, 9-phenyl-1,2,3,4,4a,9a-hexa­hydro­triptycene, C₂₆H₂₄, (II), with bonds to the quaternary-C atoms exhibiting significant elongation [1.581 (2) Å in (I) and 1.585 (2) Å in (II)]. The molecular geometry precludes significant σ–π overlap between the phenyl groups and the interannular bonds in both compounds, indicating that the origin of the bond lengthening is steric in nature.

S1. Comment

The double bond of (I) is proximal to the phenyl substituent. This regiochemistry is consistent with a stepwise mechanism for formation of (I) which involves the more stable biradical intermediate (Kaupp & Teufel, 1980; Wang et al., 1982). The cyclohexenyl ring in (II) adopts a boat conformation. Two H atoms (determined by NMR decoupling experiments to be attached to C12 and C15) are found to be highly shielded in the NMR spectrum of (II). The endo H atoms H12A and H15A are assigned to these resonances at 0.22 and 0.78 p.p.m., respectively. A single hydrogen (H15A) of (I) appears at a similarly high field (0.84 p.p.m.). The large shieldings of H15A and H12A are ascribed to their positions within the anisotropic shielding regions of two (for H15A) or three (for H12A) neighboring benzene rings.

Bond distances about carbon atoms C9 and C10 are similar in (I) and (II), and indicate the presence of significant steric effects involving the phenyl group attached to C9. Thus, the bond distances involving the bicyclic framework about C9 are observed to be 0.022–0.050 Å longer than the corresponding distances about C10. For example, the interannular C9—C11 bond is 1.581 (2) Å in (I) and 1.585 (2) Å in (II), whereas the related C10—C16 bond distances are 1.559 (2) Å in (I) and 1.550 (2) Å in (II). The phenyl substituents are rotated slightly from the plane defined by the bridgehead carbons (C9, C10, C11 and C16). The dihedral angle between this plane and the plane of the phenyl groups is 12.08 (7) in (I) and 13.39 (8) in (II). This orientation precludes significant hyperconjugation between the phenyl substituent and the C9—C11 σ bond, and discounts σ-π through-bond coupling (Osawa et al., 1983) as contributing to elongation of the bonds in these molecules (Baldridge et al., 1997). One carbon (C12) of the double bond of (I) exhibits a close contact [3.022 (2) Å] with a carbon (C8a) of the subjacent phenyl ring. However, the resulting π-π interactions (Dougherty et al., 1986), if any, do not contribute to lengthening of the C9—C11 bond, which is 0.004 Å longer in (II) (in which this bond is saturated) than in (I).

The cell constant of (I) and (II) are similar. Except for atoms near the double bond of (I), the structures of (I) and (II) are nearly superimposable. The resemblance of the polycyclic frameworks of (I) and (II) apparently allows for similar packing (Figs. 3 and 4).

S2. Experimental

A Pyrex irradiation vessel equipped with argon inlet and Teflon-coated magnetic stirbar was charged with benzene (56 ml), 9-phenylanthracene (151 mg, 0.59 mmol), and 1,3-cyclohexadiene (5.9 ml, 1.0 M) (Kaupp & Teufel, 1980). The solution was deaerated by purging with argon for 30 min prior to irradiation. Irradiation of the solution was performed with stirring under argon, using a Hanovia 450 W medium pressure mercury lamp housed in a water-cooled quartz immersion well. A cylindrical uranium glass filter was used to cut off light with wavelengths shorter than about 330 nm. The temperature of the solution during irradiation was maintained at 292 + 2 K. Progress of the reaction was monitored by means of thin-layer chromatography and NMR spectroscopic analysis. When complete (3 h), the irradiation was stopped and the solvent was evaporated under reduced pressure. The crude product was chromatographed over Woelm (activity I) alumina. Products eluted fractionally with dichloromethane and petroleum ether. Fractions determined to contain adduct (I) were combined and recrystallized from dichloromethane-ethanol to afford colorless prisms, m.p. 459 K, proton NMR (chloroform-d): 7.56 (m), 7.47 (m), 7.31 (m), 7.11 (m), 6.92 (m), 6.25 (d, 7.7 Hz), 5.78 (m), 5.68 (m), 4.18 (d, 1.9 Hz), 3.07 (bd, 10.0 Hz), 2.42 (m), 1.88 (m), 1.67 (m), 1.23 (m), 0.84 p.p.m. (m). Adduct (I) (100 mg) was dissolved in 50 ml e thyl acetate in a 100 ml round-bottom flask containing a magnetic stirbar, and 25 mg 10% Pd/C powder was added. The stirred suspension was deaerated by repeated evacuation and charging with hydrogen gas. Hydrogenation was effected by allowing the mixture to stir for 24 h at room temperature under a slight positive pressure of hydrogen (although the initial uptake of hydrogen was rapid, suggesting that the reaction probably was complete in about 30 min). The product was collected by filtration through celite, and the solvent was removed at reduced pressure. The crude product was passed through a short column of Woelm alumina (ICN, activity I) eluting with dichloromethane-petroleum ether. Fractions containing product (II) were combined and recrystallized from ethyl acetate to afford 87 mg (86%) of colorless needles, proton NMR (chloroform-d): 7.55 (m), 7.42 (m), 7.32 (m), 7.05–7.19 (m), 6.91 (m), 6.20 (d, 8.1 Hz), 4.06 (d, 8.1), 2.46 (m), 2.04 (m), 1.64 (m), 1.27- 1.53 (m), 0.78 (m), 0.22 (m).

S3. Refinement

H atoms were were located but not refined; for (I) the temperature factors of hydrogen were refined in the early stages of refinement, but were fixed in the later stages.

Computing details

For both compounds, data collection: CAD-4-PC (Enraf-Nonius, 1993); cell refinement: SET4 and CELDIM in CAD-4-PC; data reduction: DATRD2 in NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SOLVER in NRCVAX; program(s) used to refine structure: LSTSQ in NRCVAX; molecular graphics: NRCVAX; software used to prepare material for publication: TABLES in NRCVAX (January 94 version).

Figures

	Fig. 1. ORTEPII (Johnson, 1976) representation of (I) with displacement ellipsoids at 30% probability showing the atom numbering scheme.
	Fig. 2. ORTEPII (Johnson, 1976) of (II) (30% probability) showing the atom numbering scheme.
	Fig. 3. Packing diagram of (I), projection along the c axis.
	Fig. 4. Packing diagram of (II), projection along the c axis.

(I) cis-9-Phenyl-3,4,4a,9,9a,10-hexahydro-9,10[1',2']benzenoanthracene

Crystal data

C26H22	F(000) = 356.10
Mr = 334.46	? #Insert any comments here.
Triclinic, P1	Dx = 1.248 Mg m^−3
a = 9.3991 (7) Å	Mo Kα radiation, λ = 0.70930 Å
b = 9.7733 (4) Å	Cell parameters from 25 reflections
c = 10.5899 (7) Å	θ = 7.9–18.3°
α = 90.376 (4)°	µ = 0.07 mm^−1
β = 71.465 (5)°	T = 293 K
γ = 104.463 (5)°	Prism, colorless
V = 890.29 (10) Å^3	0.48 × 0.47 × 0.47 mm
Z = 2

Data collection

Nonius CAD-4 diffractometer	Rint = 0.009
Radiation source: xray tube	θmax = 24.9°, θmin = 0.0°
Graphite monochromator	h = −11→10
ω scan b/P/b	k = 0→11
3306 measured reflections	l = −12→12
3120 independent reflections	5 standard reflections every 120 min
2527 reflections with Inet > 2.0σ(Inet)	intensity decay: 1.5%

Refinement

Refinement on F	H-atom parameters not refined
Least-squares matrix: block diagonal per atom	1/[σ^2(F) + 0.0003F^2]
R[F^2 > 2σ(F^2)] = 0.042	(Δ/σ)max < 0.001
wR(F^2) = 0.050	Δρmax = 0.16 e Å^−3
S = 2.03	Δρmin = −0.20 e Å^−3
2526 reflections	Extinction correction: Larson (1970)
236 parameters	Extinction coefficient: 0.79 (11)

Special details

Experimental. ? #Insert any special details here.

Refinement. ? #Insert any special details here.

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

	x	y	z	Uiso*/Ueq
C1	0.66296 (18)	0.78052 (16)	0.96484 (16)	0.0400 (10)
C2	0.82338 (19)	0.81725 (18)	0.93994 (18)	0.0486 (10)
C3	0.88355 (19)	0.82162 (18)	1.04308 (2)	0.0505 (11)
C4	0.78480 (18)	0.79082 (17)	1.17357 (18)	0.0449 (11)
C4a	0.62561 (17)	0.75557 (16)	1.19930 (16)	0.0361 (9)
C5	0.34789 (19)	0.88392 (17)	1.45918 (16)	0.0432 (10)
C6	0.2395 (2)	0.95896 (19)	1.46574 (17)	0.0510 (11)
C7	0.1725 (2)	0.95238 (19)	1.36688 (18)	0.0502 (11)
C8	0.21343 (18)	0.87095 (17)	1.25958 (16)	0.0406 (10)
C8a	0.32545 (16)	0.79899 (15)	1.24967 (14)	0.0332 (8)
C9	0.38382 (16)	0.70242 (15)	1.14113 (15)	0.0321 (8)
C9a	0.56354 (17)	0.74977 (15)	1.09536 (15)	0.0340 (9)
C10	0.50456 (17)	0.71465 (16)	1.33420 (15)	0.0373 (9)
C10a	0.39132 (17)	0.80403 (16)	1.35164 (15)	0.0359 (9)
C11	0.33687 (17)	0.55181 (15)	1.21896 (15)	0.0337 (9)
C12	0.16317 (18)	0.48710 (17)	1.27215 (16)	0.0419 (10)
C13	0.09612 (19)	0.39442 (18)	1.37731 (18)	0.0481 (10)
C14	0.1827 (2)	0.36218 (19)	1.46361 (19)	0.0546 (11)
C15	0.30132 (19)	0.49778 (18)	1.46931 (16)	0.0440 (10)
C16	0.41399 (17)	0.55831 (16)	1.33088 (15)	0.0358 (9)
C17	0.32674 (16)	0.70455 (16)	1.02133 (15)	0.0336 (8)
C18	0.26641 (19)	0.58167 (16)	0.96789 (16)	0.0406 (9)
C19	0.2199 (2)	0.58919 (18)	0.85687 (17)	0.0484 (11)
C20	0.2345 (2)	0.7178 (2)	0.79633 (17)	0.0499 (11)
C21	0.2982 (2)	0.84099 (18)	0.84534 (17)	0.0467 (10)
C22	0.34306 (18)	0.83335 (17)	0.95686 (16)	0.0399 (9)
H1	0.6218	0.7800	0.8904	0.037*
H2	0.8917	0.8367	0.8487	0.063*
H3	0.9984	0.8466	1.0253	0.068*
H4	0.8233	0.7924	1.2494	0.051*
H5	0.3940	0.8840	1.5311	0.049*
H6	0.2125	1.0157	1.5392	0.061*
H7	0.0932	1.0069	1.3701	0.062*
H8	0.1647	0.8689	1.1876	0.043*
H10	0.5515	0.7242	1.4091	0.036*
H11	0.3805	0.4886	1.1532	0.036*
H12	0.1030	0.5117	1.2195	0.047*
H13	−0.0148	0.3554	1.4039	0.062*
H14A	0.1119	0.3308	1.5534	0.073*
H14B	0.2435	0.2901	1.4249	0.073*
H15A	0.2453	0.5713	1.5066	0.047*
H15B	0.3603	0.4813	1.5308	0.047*
H16	0.4882	0.5015	1.3074	0.039*
H18	0.2581	0.4894	1.0062	0.033*
H19	0.1764	0.4992	0.8231	0.057*
H20	0.2016	0.7244	0.7183	0.058*
H21	0.3111	0.9348	0.8039	0.053*
H22	0.3868	0.9196	0.9911	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0409 (9)	0.0337 (9)	0.0423 (10)	0.0094 (7)	−0.0097 (8)	−0.0033 (7)
C2	0.0381 (9)	0.0410 (10)	0.0539 (11)	0.0059 (7)	−0.0007 (8)	0.0018 (8)
C3	0.0298 (9)	0.0449 (10)	0.0703 (13)	0.0043 (7)	−0.0116 (9)	−0.0012 (9)
C4	0.0342 (9)	0.0421 (10)	0.0590 (11)	0.0055 (7)	−0.0194 (8)	−0.0030 (8)
C4a	0.0334 (8)	0.0310 (8)	0.0437 (9)	0.0052 (6)	−0.0147 (7)	−0.0018 (7)
C5	0.0464 (10)	0.0395 (9)	0.0378 (9)	0.0005 (8)	−0.0140 (8)	−0.0066 (7)
C6	0.0543 (11)	0.0455 (10)	0.0459 (10)	0.0123 (9)	−0.0072 (9)	−0.0157 (8)
C7	0.0476 (10)	0.0487 (10)	0.0530 (11)	0.0203 (8)	−0.0089 (9)	−0.0094 (8)
C8	0.0374 (9)	0.0414 (9)	0.0446 (10)	0.0123 (7)	−0.0138 (8)	−0.0055 (7)
C8a	0.0320 (8)	0.0295 (8)	0.0360 (9)	0.0041 (6)	−0.0110 (7)	−0.0043 (6)
C9	0.0311 (8)	0.0315 (8)	0.0348 (8)	0.0074 (6)	−0.0132 (7)	−0.0050 (6)
C9a	0.0334 (8)	0.0268 (8)	0.0418 (9)	0.0072 (6)	−0.0131 (7)	−0.0050 (6)
C10	0.0356 (8)	0.0388 (9)	0.0392 (9)	0.0045 (7)	−0.0184 (7)	−0.0026 (7)
C10a	0.0336 (8)	0.0326 (8)	0.0376 (9)	0.0014 (6)	−0.0119 (7)	−0.0027 (7)
C11	0.0331 (8)	0.0307 (8)	0.0369 (8)	0.0067 (6)	−0.0123 (7)	−0.0046 (6)
C12	0.0363 (9)	0.0447 (10)	0.0444 (10)	0.0036 (7)	−0.0185 (8)	−0.0045 (8)
C13	0.0376 (9)	0.0487 (10)	0.0503 (11)	−0.0022 (8)	−0.0142 (8)	−0.0005 (8)
C14	0.0482 (11)	0.0509 (11)	0.0572 (12)	0.0012 (9)	−0.0155 (9)	0.0115 (9)
C15	0.0405 (9)	0.0499 (10)	0.0414 (9)	0.0062 (8)	−0.0171 (8)	0.0052 (8)
C16	0.0315 (8)	0.0363 (9)	0.0402 (9)	0.0085 (7)	−0.0131 (7)	−0.0011 (7)
C17	0.0305 (8)	0.0357 (8)	0.0349 (8)	0.0083 (6)	−0.0113 (7)	−0.0055 (7)
C18	0.0480 (10)	0.0349 (9)	0.0411 (9)	0.0093 (7)	−0.0187 (8)	−0.0049 (7)
C19	0.0584 (11)	0.0463 (10)	0.0443 (10)	0.0090 (8)	−0.0256 (9)	−0.0132 (8)
C20	0.0558 (11)	0.0594 (12)	0.0384 (10)	0.0125 (9)	−0.0227 (8)	−0.0037 (8)
C21	0.0515 (10)	0.0442 (10)	0.0444 (10)	0.0107 (8)	−0.0169 (8)	0.0044 (8)
C22	0.0407 (9)	0.0374 (9)	0.0414 (9)	0.0068 (7)	−0.0159 (8)	−0.0038 (7)

Geometric parameters (Å, º)

C1—C2	1.396 (2)	C10—H10	1.017
C1—C9a	1.385 (2)	C11—C12	1.512 (2)
C1—H1	0.982	C11—C16	1.567 (2)
C2—C3	1.376 (3)	C11—H11	0.987
C2—H2	0.964	C12—C13	1.319 (2)
C3—C4	1.384 (3)	C12—H12	0.979
C3—H3	1.000	C13—C14	1.484 (3)
C4—C4a	1.384 (2)	C13—H13	0.963
C4—H4	0.979	C14—C15	1.519 (2)
C4a—C9a	1.395 (2)	C14—H14A	0.970
C4a—C10	1.497 (2)	C14—H14B	1.019
C5—C6	1.381 (3)	C15—C16	1.527 (2)
C5—C10a	1.388 (2)	C15—H15A	1.002
C5—H5	0.989	C15—H15B	1.017
C6—C7	1.377 (3)	C16—H16	0.968
C6—H6	0.957	C17—C18	1.393 (2)
C7—C8	1.391 (2)	C17—C22	1.386 (2)
C7—H7	1.011	C18—C19	1.387 (2)
C8—C8a	1.383 (2)	C18—H18	0.966
C8—H8	1.004	C19—C20	1.371 (3)
C8a—C9	1.535 (2)	C19—H19	0.988
C8a—C10a	1.400 (2)	C20—C21	1.380 (2)
C9—C9a	1.547 (2)	C20—H20	0.977
C9—C11	1.581 (2)	C21—C22	1.383 (2)
C9—C17	1.528 (2)	C21—H21	0.982
C10—C10a	1.506 (2)	C22—H22	0.963
C10—C16	1.559 (2)
C2—C1—C9a	119.33 (15)	C9—C11—C12	113.35 (12)
C2—C1—H1	120.0	C9—C11—C16	110.59 (11)
C9a—C1—H1	120.7	C9—C11—H11	106.3
C1—C2—C3	120.91 (16)	C12—C11—C16	112.22 (12)
C1—C2—H2	118.8	C12—C11—H11	106.5
C3—C2—H2	120.3	C16—C11—H11	107.4
C2—C3—C4	120.02 (15)	C11—C12—C13	122.69 (14)
C2—C3—H3	121.0	C11—C12—H12	116.1
C4—C3—H3	119.0	C13—C12—H12	121.1
C3—C4—C4a	119.48 (16)	C12—C13—C14	122.02 (15)
C3—C4—H4	122.4	C12—C13—H13	118.2
C4a—C4—H4	118.2	C14—C13—H13	119.4
C4—C4a—C9a	120.90 (15)	C13—C14—C15	107.96 (14)
C4—C4a—C10	125.64 (14)	C13—C14—H14A	109.9
C9a—C4a—C10	113.40 (13)	C13—C14—H14B	111.9
C6—C5—C10a	119.97 (15)	C15—C14—H14A	108.6
C6—C5—H5	121.2	C15—C14—H14B	106.7
C10a—C5—H5	118.8	H14A—C14—H14B	111.6
C5—C6—C7	120.01 (15)	C14—C15—C16	112.15 (14)
C5—C6—H6	119.2	C14—C15—H15A	108.8
C7—C6—H6	120.8	C14—C15—H15B	110.5
C6—C7—C8	120.53 (15)	C16—C15—H15A	106.7
C6—C7—H7	121.0	C16—C15—H15B	110.6
C8—C7—H7	118.5	H15A—C15—H15B	107.9
C7—C8—C8a	119.99 (15)	C10—C16—C11	108.69 (12)
C7—C8—H8	119.4	C10—C16—C15	111.02 (13)
C8a—C8—H8	120.6	C10—C16—H16	108.1
C8—C8a—C9	127.67 (13)	C11—C16—C15	114.67 (12)
C8—C8a—C10a	119.22 (14)	C11—C16—H16	108.2
C9—C8a—C10a	112.99 (13)	C15—C16—H16	105.9
C8a—C9—C9a	106.65 (11)	C9—C17—C18	122.85 (13)
C8a—C9—C11	104.22 (11)	C9—C17—C22	119.49 (13)
C8a—C9—C17	114.74 (12)	C18—C17—C22	117.56 (14)
C9a—C9—C11	105.42 (11)	C17—C18—C19	120.70 (15)
C9a—C9—C17	110.37 (12)	C17—C18—H18	120.7
C11—C9—C17	114.68 (12)	C19—C18—H18	118.6
C1—C9a—C4a	119.36 (14)	C18—C19—C20	120.64 (15)
C1—C9a—C9	126.40 (13)	C18—C19—H19	117.9
C4a—C9a—C9	114.20 (13)	C20—C19—H19	121.5
C4a—C10—C10a	108.34 (12)	C19—C20—C21	119.61 (15)
C4a—C10—C16	106.18 (12)	C19—C20—H20	121.3
C4a—C10—H10	112.4	C21—C20—H20	119.0
C10a—C10—C16	107.14 (12)	C20—C21—C22	119.68 (15)
C10a—C10—H10	111.5 (8)	C20—C21—H21	121.7
C16—C10—H10	111.1	C22—C21—H21	118.6
C5—C10a—C8a	120.22 (14)	C17—C22—C21	121.78 (14)
C5—C10a—C10	125.27 (14)	C17—C22—H22	118.8
C8a—C10a—C10	114.48 (13)	C21—C22—H22	119.4
C9a—C1—C2—C3	0.77 (18)	C8a—C9—C11—C16	−59.1 (2)
C2—C1—C9a—C4a	−0.25 (18)	C9a—C9—C11—C12	−180.0 (3)
C2—C1—C9a—C9	−177.8 (4)	C9a—C9—C11—C16	53.00 (19)
C1—C2—C3—C4	−0.69 (18)	C17—C9—C11—C12	−58.4 (2)
C2—C3—C4—C4a	0.08 (18)	C17—C9—C11—C16	174.6 (3)
C3—C4—C4a—C9a	0.44 (18)	C8a—C9—C17—C18	−133.1 (3)
C3—C4—C4a—C10	177.6 (4)	C8a—C9—C17—C22	50.8 (2)
C4—C4a—C9a—C1	−0.35 (18)	C9a—C9—C17—C18	106.4 (3)
C4—C4a—C9a—C9	177.5 (4)	C9a—C9—C17—C22	−69.7 (2)
C10—C4a—C9a—C1	−177.9 (4)	C11—C9—C17—C18	−12.48 (16)
C10—C4a—C9a—C9	−0.06 (15)	C11—C9—C17—C22	171.4 (3)
C4—C4a—C10—C10a	129.1 (3)	C4a—C10—C10a—C5	−127.5 (3)
C4—C4a—C10—C16	−116.1 (3)	C4a—C10—C10a—C8a	54.2 (2)
C9a—C4a—C10—C10a	−53.5 (2)	C16—C10—C10a—C5	118.3 (3)
C9a—C4a—C10—C16	61.3 (2)	C16—C10—C10a—C8a	−60.0 (2)
C10a—C5—C6—C7	1.21 (18)	C4a—C10—C16—C11	−60.7 (2)
C6—C5—C10a—C8a	−0.10 (18)	C4a—C10—C16—C15	172.3 (3)
C6—C5—C10a—C10	−178.3 (4)	C10a—C10—C16—C11	55.0 (2)
C5—C6—C7—C8	−0.26 (18)	C10a—C10—C16—C15	−72.0 (2)
C6—C7—C8—C8a	−1.83 (18)	C9—C11—C12—C13	−153.8 (4)
C7—C8—C8a—C9	178.8 (4)	C16—C11—C12—C13	−27.59 (19)
C7—C8—C8a—C10a	2.91 (18)	C9—C11—C16—C10	3.35 (14)
C8—C8a—C9—C9a	131.9 (3)	C9—C11—C16—C15	128.2 (3)
C8—C8a—C9—C11	−116.9 (3)	C12—C11—C16—C10	−124.3 (3)
C8—C8a—C9—C17	9.36 (16)	C12—C11—C16—C15	0.59 (16)
C10a—C8a—C9—C9a	−52.0 (2)	C11—C12—C13—C14	9.18 (17)
C10a—C8a—C9—C11	59.2 (2)	C12—C13—C14—C15	34.6 (2)
C10a—C8a—C9—C17	−174.5 (3)	C13—C14—C15—C16	−58.5 (2)
C8—C8a—C10a—C5	−1.96 (18)	C14—C15—C16—C10	165.0 (4)
C8—C8a—C10a—C10	176.4 (3)	C14—C15—C16—C11	41.3 (2)
C9—C8a—C10a—C5	−178.4 (3)	C9—C17—C18—C19	−178.3 (4)
C9—C8a—C10a—C10	−0.03 (15)	C22—C17—C18—C19	−2.11 (18)
C8a—C9—C9a—C1	−129.7 (3)	C9—C17—C22—C21	177.8 (4)
C8a—C9—C9a—C4a	52.7 (2)	C18—C17—C22—C21	1.47 (18)
C11—C9—C9a—C1	119.9 (3)	C17—C18—C19—C20	0.96 (18)
C11—C9—C9a—C4a	−57.7 (2)	C18—C19—C20—C21	0.92 (18)
C17—C9—C9a—C1	−4.44 (16)	C19—C20—C21—C22	−1.56 (18)
C17—C9—C9a—C4a	177.9 (3)	C20—C21—C22—C17	0.35 (18)
C8a—C9—C11—C12	67.9 (2)

(II) cis-9-Phenyl-1,2,3,4,4a,9,9a,10-octahydro-9,10[1',2']benzenoanthracene

Crystal data

C26H24	F(000) = 360.10
Mr = 336.47	? #Insert any comments here.
Triclinic, P1	Dx = 1.243 Mg m^−3
a = 9.2213 (6) Å	Mo Kα radiation, λ = 0.70930 Å
b = 9.8777 (10) Å	Cell parameters from 25 reflections
c = 10.7390 (8) Å	θ = 8.4–17.6°
α = 90.738 (8)°	µ = 0.07 mm^−1
β = 107.829 (6)°	T = 293 K
γ = 104.052 (7)°	Needle, colorless
V = 899.28 (13) Å^3	0.30 × 0.30 × 0.30 mm
Z = 2

Data collection

Nonius CAD-4 diffractometer	Rint = 0.014
Radiation source: xray tube	θmax = 25.0°, θmin = 2.0°
Graphite monochromator	h = −10→10
ω scan b/P/b	k = 0→11
3334 measured reflections	l = −12→12
3147 independent reflections	3 standard reflections every 120 min
2444 reflections with Inet > 2.0σ(Inet)	intensity decay: 1.5%

Refinement

Refinement on F	H-atom parameters not refined
Least-squares matrix: full	1/[σ^2(F) + 0.0002F^2]
R[F^2 > 2σ(F^2)] = 0.041	(Δ/σ)max < 0.001
wR(F^2) = 0.044	Δρmax = 0.15 e Å^−3
S = 1.94	Δρmin = −0.17 e Å^−3
2442 reflections	Extinction correction: Larson (1970)
236 parameters	Extinction coefficient: 0.57 (7)

Special details

Experimental. ? #Insert any special details here.

Refinement. ? #Insert any special details here.

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

	x	y	z	Uiso*/Ueq
C1	0.66684 (19)	0.78197 (17)	0.02077 (16)	0.0381 (11)
C2	0.8285 (2)	0.81943 (19)	0.04288 (18)	0.0458 (11)
C3	0.8879 (2)	0.82325 (19)	−0.06063 (19)	0.0488 (11)
C4	0.7860 (2)	0.79172 (19)	−0.18781 (18)	0.0429 (11)
C4a	0.62543 (18)	0.75632 (16)	−0.21079 (16)	0.0350 (9)
C5	0.34505 (2)	0.88662 (18)	−0.45824 (17)	0.0432 (11)
C6	0.2390 (2)	0.96387 (19)	−0.45991 (19)	0.0523 (12)
C7	0.1731 (2)	0.95932 (19)	−0.3605 (2)	0.0513 (12)
C8	0.2139 (2)	0.87746 (18)	−0.25780 (18)	0.0422 (11)
C8a	0.32483 (18)	0.80348 (16)	−0.25194 (16)	0.0342 (9)
C9	0.38185 (18)	0.70552 (16)	−0.14901 (15)	0.0317 (9)
C9a	0.56357 (18)	0.75029 (16)	−0.10652 (16)	0.0325 (10)
C10	0.50039 (19)	0.71614 (17)	−0.34281 (16)	0.0371 (10)
C10a	0.38867 (18)	0.80692 (16)	−0.35502 (16)	0.0363 (10)
C11	0.32988 (19)	0.55663 (16)	−0.22954 (15)	0.0338 (9)
C12	0.15118 (19)	0.50022 (18)	−0.28968 (17)	0.0419 (10)
C13	0.1079 (2)	0.35693 (19)	−0.36541 (18)	0.0502 (11)
C14	0.1970 (2)	0.35330 (19)	−0.46305 (19)	0.0531 (12)
C15	0.2932 (2)	0.49818 (19)	−0.47310 (17)	0.0431 (10)
C16	0.41032 (19)	0.56257 (17)	−0.33911 (16)	0.0361 (9)
C17	0.32604 (18)	0.70707 (16)	−0.02911 (15)	0.0331 (9)
C18	0.2687 (2)	0.58597 (18)	0.02368 (17)	0.0421 (10)
C19	0.2249 (2)	0.59227 (19)	0.13564 (18)	0.0508 (12)
C20	0.2406 (2)	0.7187 (2)	0.19886 (18)	0.0523 (12)
C21	0.3013 (2)	0.84058 (19)	0.15060 (18)	0.0484 (11)
C22	0.3436 (2)	0.83423 (17)	0.03818 (17)	0.0400 (10)
H1	0.624	0.781	0.096	0.038*
H2	0.902	0.842	0.134	0.060*
H3	1.000	0.846	−0.044	0.053*
H4	0.829	0.795	−0.262	0.048*
H5	0.390	0.887	−0.532	0.049*
H6	0.209	1.023	−0.532	0.066*
H7	0.094	1.012	−0.363	0.067*
H8	0.167	0.877	−0.188	0.042*
H10	0.547	0.724	−0.417	0.036*
H11	0.371	0.488	−0.165	0.036*
H12A	0.110	0.570	−0.349	0.049*
H12B	0.096	0.495	−0.221	0.040*
H13A	−0.009	0.329	−0.411	0.070*
H13B	0.131	0.287	−0.301	0.087*
H14A	0.123	0.311	−0.551	0.083*
H14B	0.271	0.293	−0.432	0.073*
H15A	0.223	0.560	−0.509	0.050*
H15B	0.353	0.492	−0.535	0.043*
H16	0.490	0.505	−0.312	0.041*
H18	0.261	0.496	−0.016	0.044*
H19	0.185	0.506	0.171	0.056*
H20	0.205	0.726	0.277	0.066*
H21	0.316	0.931	0.194	0.053*
H22	0.386	0.922	0.006	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0395 (10)	0.0355 (10)	0.0382 (10)	0.0074 (8)	0.0128 (8)	0.0033 (8)
C2	0.0367 (10)	0.0481 (11)	0.0445 (11)	0.0057 (8)	0.0055 (9)	0.0005 (9)
C3	0.0292 (9)	0.0527 (12)	0.0593 (13)	0.0027 (8)	0.0133 (9)	−0.0014 (10)
C4	0.0337 (10)	0.0475 (11)	0.0476 (11)	0.0042 (8)	0.0182 (9)	−0.0002 (9)
C4a	0.0322 (9)	0.0327 (9)	0.0399 (10)	0.0052 (7)	0.0139 (8)	0.0000 (7)
C5	0.0456 (11)	0.0369 (10)	0.0389 (10)	−0.0019 (8)	0.0115 (9)	0.0052 (8)
C6	0.0566 (12)	0.0405 (11)	0.0494 (12)	0.0076 (9)	0.0054 (10)	0.0117 (9)
C7	0.0480 (11)	0.0435 (11)	0.0575 (13)	0.0165 (9)	0.0063 (10)	0.0048 (10)
C8	0.0392 (10)	0.0395 (10)	0.0485 (11)	0.0104 (8)	0.0147 (9)	0.0032 (8)
C8a	0.0312 (9)	0.0310 (9)	0.0385 (10)	0.0031 (7)	0.0123 (8)	0.0010 (7)
C9	0.0302 (8)	0.0312 (9)	0.0349 (9)	0.0058 (7)	0.0139 (7)	0.0017 (7)
C9a	0.0317 (9)	0.0283 (9)	0.0379 (10)	0.0061 (7)	0.0129 (8)	0.0021 (7)
C10	0.0354 (9)	0.0429 (10)	0.0348 (10)	0.0051 (8)	0.0178 (8)	0.0003 (8)
C10a	0.0347 (9)	0.0332 (9)	0.0364 (10)	0.0009 (7)	0.0109 (8)	0.0006 (8)
C11	0.0347 (9)	0.0320 (9)	0.0341 (9)	0.0057 (7)	0.0126 (7)	0.0003 (7)
C12	0.0365 (10)	0.0452 (10)	0.0420 (10)	0.0006 (8)	0.0180 (8)	−0.0050 (8)
C13	0.0517 (11)	0.0441 (11)	0.0464 (11)	−0.0038 (9)	0.0168 (9)	−0.0044 (9)
C14	0.0507 (12)	0.0485 (12)	0.0541 (12)	0.0028 (9)	0.0170 (10)	−0.0131 (9)
C15	0.0425 (10)	0.0496 (11)	0.0372 (10)	0.0067 (8)	0.0170 (8)	−0.0049 (8)
C16	0.0343 (9)	0.0381 (10)	0.0362 (9)	0.0078 (7)	0.0129 (8)	−0.0012 (8)
C17	0.0298 (8)	0.0347 (9)	0.0345 (9)	0.0063 (7)	0.0116 (7)	0.0013 (7)
C18	0.0515 (11)	0.0360 (10)	0.0413 (10)	0.0086 (8)	0.0208 (9)	0.0004 (8)
C19	0.0644 (13)	0.0467 (11)	0.0439 (11)	0.0058 (10)	0.0277 (10)	0.0075 (9)
C20	0.0580 (12)	0.0614 (13)	0.0409 (11)	0.0094 (10)	0.0256 (10)	−0.0015 (10)
C21	0.0511 (11)	0.0463 (11)	0.0475 (11)	0.0063 (9)	0.0207 (9)	−0.0109 (9)
C22	0.0394 (10)	0.0362 (10)	0.0449 (10)	0.0041 (8)	0.0187 (8)	−0.0008 (8)

Geometric parameters (Å, º)

C1—C2	1.389 (2)	C11—C12	1.528 (2)
C1—C9a	1.386 (2)	C11—C16	1.566 (2)
C1—H1	1.00	C11—H11	1.03
C2—C3	1.378 (3)	C12—C13	1.524 (2)
C2—H2	0.99	C12—H12A	1.01
C3—C4	1.381 (3)	C12—H12B	1.01
C3—H3	0.96	C13—C14	1.522 (3)
C4—C4a	1.378 (2)	C13—H13A	1.01
C4—H4	0.98	C13—H13B	0.99
C4a—C9a	1.400 (2)	C14—C15	1.514 (3)
C4a—C10	1.503 (2)	C14—H14A	1.00
C5—C6	1.374 (3)	C14—H14B	1.00
C5—C10a	1.384 (2)	C15—C16	1.527 (2)
C5—H5	1.00	C15—H15A	0.99
C6—C7	1.377 (3)	C15—H15B	1.00
C6—H6	0.99	C16—H16	1.01
C7—C8	1.389 (3)	C17—C18	1.388 (2)
C7—H7	0.98	C17—C22	1.390 (2)
C8—C8a	1.382 (2)	C18—C19	1.386 (2)
C8—H8	0.97	C18—H18	0.96
C8a—C9	1.534 (2)	C19—C20	1.368 (3)
C8a—C10a	1.401 (2)	C19—H19	0.98
C9—C9a	1.542 (2)	C20—C21	1.378 (3)
C9—C11	1.585 (2)	C20—H20	1.00
C9—C17	1.527 (2)	C21—C22	1.383 (2)
C10—C10a	1.500 (2)	C21—H21	0.96
C10—C16	1.550 (2)	C22—H22	0.98
C10—H10	1.01
C2—C1—C9a	119.94 (15)	C12—C11—C16	110.19 (13)
C2—C1—H1	120.7	C12—C11—H11	108.4
C9a—C1—H1	119.3	C16—C11—H11	107.4
C1—C2—C3	120.65 (16)	C11—C12—C13	111.27 (14)
C1—C2—H2	119.5	C11—C12—H12A	108.1
C3—C2—H2	119.8	C11—C12—H12B	112.0
C2—C3—C4	119.87 (15)	C13—C12—H12A	110.9
C2—C3—H3	119.8	C13—C12—H12B	109.9
C4—C3—H3	120.3	H12A—C12—H12B	104.5
C3—C4—C4a	119.89 (16)	C12—C13—C14	113.13 (14)
C3—C4—H4	119.7	C12—C13—H13A	108.3
C4a—C4—H4	120.4	C12—C13—H13B	108.2
C4—C4a—C9a	120.84 (15)	C14—C13—H13A	111.2
C4—C4a—C10	126.02 (15)	C14—C13—H13B	109.1
C9a—C4a—C10	113.10 (13)	H13A—C13—H13B	106.7
C6—C5—C10a	120.10 (16)	C13—C14—C15	111.48 (14)
C6—C5—H5	120.3	C13—C14—H14A	110.6
C10a—C5—H5	119.6	C13—C14—H14B	108.4
C5—C6—C7	120.05 (16)	C15—C14—H14A	110.3
C5—C6—H6	120.9	C15—C14—H14B	108.1
C7—C6—H6	119.1	H14A—C14—H14B	107.9
C6—C7—C8	120.26 (17)	C14—C15—C16	110.77 (15)
C6—C7—H7	120.4	C14—C15—H15A	110.7
C8—C7—H7	119.3	C14—C15—H15B	109.6
C7—C8—C8a	120.41 (16)	C16—C15—H15A	109.9
C7—C8—H8	118.8	C16—C15—H15B	108.6
C8a—C8—H8	120.7	H15A—C15—H15B	107.1
C8—C8a—C9	127.93 (14)	C10—C16—C11	109.19 (12)
C8—C8a—C10a	118.66 (15)	C10—C16—C15	112.30 (14)
C9—C8a—C10a	113.24 (13)	C10—C16—H16	108.4
C8a—C9—C9a	106.04 (12)	C11—C16—C15	112.45 (13)
C8a—C9—C11	104.34 (12)	C11—C16—H16	106.4
C8a—C9—C17	115.20 (12)	C15—C16—H16	107.9
C9a—C9—C11	106.01 (12)	C9—C17—C18	122.99 (14)
C9a—C9—C17	110.25 (13)	C9—C17—C22	119.69 (14)
C11—C9—C17	114.25 (12)	C18—C17—C22	117.12 (14)
C1—C9a—C4a	118.81 (14)	C17—C18—C19	121.13 (15)
C1—C9a—C9	126.94 (14)	C17—C18—H18	120.2
C4a—C9a—C9	114.25 (14)	C19—C18—H18	118.6
C4a—C10—C10a	107.87 (13)	C18—C19—C20	120.66 (16)
C4a—C10—C16	105.55 (13)	C18—C19—H19	119.7
C4a—C10—H10	112.2	C20—C19—H19	119.6
C10a—C10—C16	108.35 (13)	C19—C20—C21	119.38 (16)
C10a—C10—H10	111.9	C19—C20—H20	121.9
C16—C10—H10	110.7	C21—C20—H20	118.6
C5—C10a—C8a	120.44 (15)	C20—C21—C22	119.92 (16)
C5—C10a—C10	125.31 (15)	C20—C21—H21	121.5
C8a—C10a—C10	114.24 (14)	C22—C21—H21	118.6
C9—C11—C12	113.48 (13)	C17—C22—C21	121.72 (15)
C9—C11—C16	110.01 (12)	C17—C22—H22	119.7
C9—C11—H11	107.2	C21—C22—H22	118.6
C9a—C1—C2—C3	−1.09 (14)	C2—C1—C9a—C4a	0.27 (14)
C2—C1—C9a—C9	179.3 (3)	C1—C2—C3—C4	1.01 (14)
C2—C3—C4—C4a	−0.12 (14)	C3—C4—C4a—C9a	−0.71 (14)
C3—C4—C4a—C10	−178.4 (3)	C4—C4a—C9a—C1	0.63 (14)
C4—C4a—C9a—C9	−178.6 (3)	C10—C4a—C9a—C1	178.6 (3)
C10—C4a—C9a—C9	−0.57 (12)	C4—C4a—C10—C10a	−127.6 (3)
C4—C4a—C10—C16	116.7 (3)	C9a—C4a—C10—C10a	54.54 (17)
C9a—C4a—C10—C16	−61.13 (18)	C10a—C5—C6—C7	−1.65 (15)
C6—C5—C10a—C8a	0.41 (15)	C6—C5—C10a—C10	178.8 (3)
C5—C6—C7—C8	0.38 (15)	C6—C7—C8—C8a	2.16 (15)
C7—C8—C8a—C9	−178.4 (3)	C7—C8—C8a—C10a	−3.35 (15)
C8—C8a—C9—C9a	−131.7 (3)	C8—C8a—C9—C11	116.6 (3)
C8—C8a—C9—C17	−9.45 (14)	C10a—C8a—C9—C9a	53.07 (17)
C10a—C8a—C9—C11	−58.63 (17)	C10a—C8a—C9—C17	175.3 (3)
C8—C8a—C10a—C5	2.08 (15)	C8—C8a—C10a—C10	−176.5 (3)
C9—C8a—C10a—C5	177.8 (3)	C9—C8a—C10a—C10	−0.71 (12)
C8a—C9—C9a—C1	128.2 (3)	C8a—C9—C9a—C4a	−52.70 (17)
C11—C9—C9a—C1	−121.3 (3)	C11—C9—C9a—C4a	57.82 (17)
C17—C9—C9a—C1	2.87 (13)	C17—C9—C9a—C4a	−178.0 (3)
C8a—C9—C11—C12	−63.59 (18)	C8a—C9—C11—C16	60.37 (17)
C9a—C9—C11—C12	−175.3 (3)	C9a—C9—C11—C16	−51.34 (16)
C17—C9—C11—C12	63.09 (18)	C17—C9—C11—C16	−173.0 (3)
C8a—C9—C17—C18	135.5 (3)	C8a—C9—C17—C22	−49.71 (17)
C9a—C9—C17—C18	−104.6 (2)	C9a—C9—C17—C22	70.22 (19)
C11—C9—C17—C18	14.70 (14)	C11—C9—C17—C22	−170.5 (3)
C4a—C10—C10a—C5	127.3 (3)	C4a—C10—C10a—C8a	−54.23 (17)
C16—C10—C10a—C5	−118.9 (3)	C16—C10—C10a—C8a	59.58 (18)
C4a—C10—C16—C11	62.58 (18)	C4a—C10—C16—C15	−172.0 (3)
C10a—C10—C16—C11	−52.76 (16)	C10a—C10—C16—C15	72.7 (2)
C9—C11—C12—C13	−179.8 (3)	C16—C11—C12—C13	56.34 (18)
C9—C11—C16—C10	−6.05 (12)	C9—C11—C16—C15	−131.4 (3)
C12—C11—C16—C10	119.8 (2)	C12—C11—C16—C15	−5.54 (13)
C11—C12—C13—C14	−50.58 (18)	C12—C13—C14—C15	−6.89 (13)
C13—C14—C15—C16	58.09 (19)	C14—C15—C16—C10	−174.8 (3)
C14—C15—C16—C11	−51.16 (17)	C9—C17—C18—C19	177.5 (3)
C22—C17—C18—C19	2.59 (15)	C9—C17—C22—C21	−177.1 (3)
C18—C17—C22—C21	−2.00 (15)	C17—C18—C19—C20	−1.49 (15)
C18—C19—C20—C21	−0.33 (15)	C19—C20—C21—C22	0.94 (15)
C20—C21—C22—C17	0.26 (15)