2,9,16,23-Tetra­kis(1-methyl­eth­yl)-5,6,11,12,13,14,19,20,25,26,27,28-dodecadehydro­tetra­benzo[a,e,k,o]cyclo­eicosene

Perera, T.; Fronczek, F.R.; Watkins, S.F.

doi:10.1107/S1600536811048604

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3493

https://doi.org/10.1107/S1600536811048604

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2,9,16,23-Tetrakis(1-methylethyl)-5,6,11,12,13,14,19,20,25,26,27,28-dodecadehydrotetrabenzo[a,e,k,o]cycloeicosene¹

Theshini Perera,^a Frank R. Fronczek ^a ^* and Steven F. Watkins ^a

^aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
^*Correspondence e-mail: ffroncz@lsu.edu

(Received 25 October 2011; accepted 15 November 2011; online 30 November 2011)

The title compound, C₄₈H₄₀, is a tetraisopropyl-substituted polyannulenoenyne. The unsubstituted polyannulenoenyne, C₃₆H₁₆ (CSD: RICVEE; CAS: 186494-87-1), has quasi-D₂ (222) symmetry, as determined by least-squares fit (excluding H atoms) to a model optimized in D₂ symmetry by molecular mechanics (r.m.s. deviation = 0.239 Å). The least-squares fits of 36 common C atoms of the title compound (at 90 K) to the parent (at 295 K) and to the optimized model show r.m.s. deviations of 0.419 and 0.426 Å, respectively.

Related literature

For a description of the Cambridge Structural Database, see: Allen (2002 ). For the synthesis and a related structure, see: Boese et al. (1997 ). For molecular mechanics software, see: Cambridgesoft (2010 ).

Experimental

Crystal data

C₄₈H₄₀
M_r = 616.8
Monoclinic, P 2₁ /c
a = 18.0007 (4) Å
b = 12.5083 (3) Å
c = 16.0674 (4) Å
β = 91.004 (1)°
V = 3617.15 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.06 mm⁻¹
T = 90 K
0.45 × 0.30 × 0.30 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor 1997 ) T_min = 0.972, T_max = 0.981
13998 measured reflections
8186 independent reflections
5354 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.127
S = 1.02
8186 reflections
442 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: IDEAL (Gould et al., 1988 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811048604/kj2194sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048604/kj2194Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048604/kj2194Isup3.cml

checkCIF report

Comment top

The title compound, C₄₈H₄₀, is a tetraisopropyl-substituted polyannulenoenyne and its structure was determined at 90 K. The 295 K structure of the unsubstituted parent annulene, C₃₆H₁₆, was previously determined by Boese et al. (1997; CSD: RICVEE, Allen, 2002; CAS: 186494–87-1), and is of quasi-D₂ (222) symmetry, as determined by least-squares fit (Gould et al., 1988; δ_r.m.s. = 0.239 Å) of all 36 common carbon atoms of the parent to a model of C₃₆H₁₆ optimized in D₂ symmetry by molecular mechanics (Cambridgesoft, 2010). Reasonable agreements result from the same least-squares fit of the title compound (at 90 K) to the parent (δ_r.m.s. =0.419 Å) and to the optimized model (δ_r.m.s. = 0.426 Å).

The six C≡C triple bond distances are all experimentally equal, falling in the narrow range 1.203 (2) - 1.206 (2) Å, while the C–C bonds linking the triple bonds have length C16—C17 1.370 (2) and C34—C35 1.377 (2) Å. The acetylenic bridges are slightly bowed outward, with C–C≡C angles in the range 177.59 (18) - 179.17 (18)° for the butadiyne bridges and in the range 174.43 (17) - 176.80 (17)° for the acetylene bridges. Distances between the following bond centroids provide a measure of overall molecular dimensions: C16—C17 to C34—C35 = 3.341 (2) Å, C7 ≡C8 to C25 ≡C26 = 7.650 (2) Å.

Related literature top

For a description of the Cambridge Structural Database, see: Allen (2002). For the synthesis and a related structure, see: Boese et al. (1997). For molecular mechanics software, see: Cambridgesoft (2010).

Experimental top

The preparation of the title compound has been described by Boese et al. (1997). Crystals were grown by slow evaporation from dichloromethane and deuterochloroform.

Structure description top

For a description of the Cambridge Structural Database, see: Allen (2002). For the synthesis and a related structure, see: Boese et al. (1997). For molecular mechanics software, see: Cambridgesoft (2010).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: IDEAL (Gould et al., 1988) and WinGX (Farrugia, 1999).

Figures top

Fig. 1. View of the title compound showing 50% probability displacement ellipsoids.

7,16,25,34-tetrakis(propan-2-yl)pentacyclo[30.4.0.0^4,9.0^14,19.0^22,27] hexatriaconta-1(32),4,6,8,14(19),15,17,22,24,26,33,35-dodecaen- 2,10,12,20,28,30-hexayne top

Crystal data top

C₄₈H₄₀	F(000) = 1312
M_r = 616.8	D_x = 1.133 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7618 reflections
a = 18.0007 (4) Å	θ = 2.6–29.1°
b = 12.5083 (3) Å	µ = 0.06 mm⁻¹
c = 16.0674 (4) Å	T = 90 K
β = 91.004 (1)°	Prism, golden yellow
V = 3617.15 (15) Å³	0.45 × 0.30 × 0.30 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	8186 independent reflections
Radiation source: sealed tube	5354 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	R_int = 0.035
Detector resolution: 9 pixels mm^-1	θ_max = 28.9°, θ_min = 2.8°
CCD rotation images, thick slices scans	h = −23→23
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor 1997)	k = −16→14
T_min = 0.972, T_max = 0.981	l = −19→20
13998 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0543P)² + 1.183P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
8186 reflections	Δρ_max = 0.25 e Å⁻³
442 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.0017 (4)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₄₈H₄₀	V = 3617.15 (15) Å³
M_r = 616.8	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.0007 (4) Å	µ = 0.06 mm⁻¹
b = 12.5083 (3) Å	T = 90 K
c = 16.0674 (4) Å	0.45 × 0.30 × 0.30 mm
β = 91.004 (1)°

Data collection top

Nonius KappaCCD diffractometer	8186 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor 1997)	5354 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.981	R_int = 0.035
13998 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.02	Δρ_max = 0.25 e Å⁻³
8186 reflections	Δρ_min = −0.28 e Å⁻³
442 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.34021 (9)	0.67572 (12)	−0.03559 (9)	0.0209 (3)
C2	0.37458 (9)	0.65496 (13)	−0.11163 (9)	0.0230 (4)
H2	0.3986	0.5882	−0.1196	0.028*
C3	0.37425 (9)	0.72994 (13)	−0.17553 (9)	0.0239 (4)
C4	0.33685 (9)	0.82602 (13)	−0.16283 (9)	0.0250 (4)
H4	0.3348	0.8774	−0.2064	0.03*
C5	0.30274 (9)	0.84840 (13)	−0.08857 (9)	0.0240 (4)
H5	0.2781	0.9149	−0.0816	0.029*
C6	0.30408 (9)	0.77426 (12)	−0.02347 (9)	0.0211 (3)
C7	0.26840 (9)	0.79587 (12)	0.05395 (9)	0.0221 (3)
C8	0.23760 (9)	0.80786 (12)	0.11918 (9)	0.0221 (3)
C9	0.20160 (8)	0.81294 (12)	0.19792 (9)	0.0215 (3)
C10	0.20544 (9)	0.90410 (13)	0.24814 (10)	0.0264 (4)
H10	0.2289	0.9669	0.2282	0.032*
C11	0.17525 (9)	0.90345 (13)	0.32691 (10)	0.0269 (4)
H11	0.1793	0.9658	0.3604	0.032*
C12	0.13916 (9)	0.81390 (13)	0.35838 (9)	0.0223 (3)
C13	0.13314 (9)	0.72469 (12)	0.30736 (9)	0.0208 (3)
H13	0.1073	0.6636	0.3267	0.025*
C14	0.16417 (8)	0.72248 (12)	0.22813 (9)	0.0198 (3)
C15	0.15945 (9)	0.62679 (12)	0.17971 (9)	0.0216 (3)
C16	0.15709 (9)	0.54517 (12)	0.13983 (9)	0.0215 (3)
C17	0.15610 (9)	0.45239 (12)	0.09457 (9)	0.0223 (3)
C18	0.15587 (9)	0.36996 (13)	0.05588 (9)	0.0232 (3)
C19	0.15470 (9)	0.27065 (12)	0.01184 (9)	0.0219 (3)
C20	0.12070 (9)	0.26396 (13)	−0.06716 (9)	0.0237 (4)
H20	0.0977	0.3257	−0.0905	0.028*
C21	0.11988 (9)	0.16932 (13)	−0.11210 (10)	0.0256 (4)
C22	0.15239 (10)	0.07952 (13)	−0.07467 (10)	0.0300 (4)
H22	0.1519	0.0136	−0.104	0.036*
C23	0.18519 (9)	0.08346 (13)	0.00358 (10)	0.0281 (4)
H23	0.2058	0.0204	0.0275	0.034*
C24	0.18827 (9)	0.17957 (12)	0.04787 (9)	0.0230 (3)
C25	0.22660 (9)	0.18904 (12)	0.12662 (10)	0.0235 (4)
C26	0.25924 (9)	0.20612 (12)	0.19125 (10)	0.0240 (4)
C27	0.29570 (9)	0.23181 (12)	0.26867 (9)	0.0228 (3)
C28	0.29559 (9)	0.16136 (14)	0.33603 (10)	0.0289 (4)
H28	0.2728	0.0932	0.3298	0.035*
C29	0.32799 (9)	0.18895 (13)	0.41168 (10)	0.0286 (4)
H29	0.3269	0.1394	0.4564	0.034*
C30	0.36228 (9)	0.28784 (13)	0.42378 (9)	0.0238 (4)
C31	0.36368 (9)	0.35806 (13)	0.35677 (9)	0.0225 (3)
H31	0.387	0.4257	0.3636	0.027*
C32	0.33159 (9)	0.33165 (12)	0.27927 (9)	0.0213 (3)
C33	0.33649 (9)	0.40474 (12)	0.21094 (9)	0.0224 (3)
C34	0.34108 (9)	0.46519 (12)	0.15295 (9)	0.0233 (4)
C35	0.34333 (9)	0.53578 (12)	0.08726 (9)	0.0232 (4)
C36	0.34260 (9)	0.59846 (12)	0.03031 (9)	0.0228 (3)
C37	0.41549 (10)	0.71348 (14)	−0.25636 (10)	0.0301 (4)
H37	0.3804	0.7324	−0.303	0.036*
C38	0.48096 (10)	0.79092 (15)	−0.26042 (11)	0.0377 (5)
H38A	0.4631	0.8642	−0.2528	0.057*
H38B	0.5045	0.7847	−0.3148	0.057*
H38C	0.5173	0.7735	−0.2163	0.057*
C39	0.44060 (12)	0.59924 (15)	−0.27061 (12)	0.0442 (5)
H39A	0.4774	0.5793	−0.2277	0.066*
H39B	0.4628	0.5934	−0.3257	0.066*
H39C	0.3977	0.5512	−0.2676	0.066*
C40	0.10830 (9)	0.81729 (13)	0.44585 (9)	0.0261 (4)
H40	0.1495	0.8419	0.4838	0.031*
C41	0.08181 (10)	0.70983 (14)	0.47865 (10)	0.0315 (4)
H41A	0.0394	0.685	0.4449	0.047*
H41B	0.0668	0.7177	0.5367	0.047*
H41C	0.1222	0.6576	0.4755	0.047*
C42	0.04634 (10)	0.89944 (14)	0.45132 (10)	0.0308 (4)
H42A	0.0642	0.9687	0.4315	0.046*
H42B	0.0309	0.9062	0.5093	0.046*
H42C	0.0039	0.8764	0.4167	0.046*
C43	0.08507 (10)	0.16014 (14)	−0.19909 (10)	0.0317 (4)
H43	0.1231	0.1266	−0.2354	0.038*
C44	0.06418 (11)	0.26707 (15)	−0.23850 (10)	0.0359 (4)
H44A	0.0244	0.3003	−0.2067	0.054*
H44B	0.0471	0.2555	−0.296	0.054*
H44C	0.1077	0.3142	−0.2381	0.054*
C45	0.01798 (11)	0.08507 (15)	−0.19878 (11)	0.0392 (5)
H45A	0.0326	0.0164	−0.1741	0.059*
H45B	0.0001	0.0736	−0.256	0.059*
H45C	−0.0217	0.1171	−0.166	0.059*
C46	0.40087 (9)	0.31230 (14)	0.50654 (9)	0.0294 (4)
H46	0.3752	0.27	0.5504	0.035*
C47	0.39803 (11)	0.42839 (15)	0.53199 (11)	0.0393 (5)
H47A	0.4255	0.4716	0.492	0.059*
H47B	0.4205	0.4367	0.5876	0.059*
H47C	0.3462	0.4522	0.5329	0.059*
C48	0.48084 (12)	0.2742 (2)	0.50436 (13)	0.0581 (7)
H48A	0.4818	0.1969	0.4948	0.087*
H48B	0.5057	0.2906	0.5576	0.087*
H48C	0.5066	0.3106	0.4592	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0265 (8)	0.0179 (8)	0.0181 (7)	−0.0032 (7)	−0.0015 (6)	0.0005 (6)
C2	0.0273 (9)	0.0204 (8)	0.0212 (8)	−0.0019 (7)	−0.0010 (6)	−0.0032 (6)
C3	0.0281 (9)	0.0263 (9)	0.0174 (8)	−0.0052 (7)	−0.0001 (6)	−0.0020 (6)
C4	0.0298 (9)	0.0244 (9)	0.0208 (8)	−0.0027 (7)	−0.0001 (7)	0.0048 (7)
C5	0.0274 (9)	0.0193 (8)	0.0251 (8)	0.0011 (7)	0.0005 (7)	0.0019 (6)
C6	0.0240 (8)	0.0198 (8)	0.0196 (8)	−0.0029 (7)	0.0001 (6)	−0.0008 (6)
C7	0.0268 (8)	0.0158 (8)	0.0238 (8)	−0.0017 (7)	−0.0011 (7)	0.0006 (6)
C8	0.0272 (8)	0.0154 (8)	0.0237 (8)	−0.0013 (7)	−0.0002 (7)	−0.0001 (6)
C9	0.0250 (8)	0.0194 (8)	0.0200 (8)	0.0021 (7)	0.0001 (6)	−0.0015 (6)
C10	0.0321 (9)	0.0175 (8)	0.0296 (9)	−0.0049 (7)	0.0045 (7)	−0.0040 (7)
C11	0.0329 (9)	0.0209 (9)	0.0269 (9)	−0.0021 (7)	0.0035 (7)	−0.0084 (7)
C12	0.0232 (8)	0.0218 (8)	0.0220 (8)	0.0043 (7)	0.0008 (6)	−0.0030 (6)
C13	0.0251 (8)	0.0170 (8)	0.0204 (8)	0.0016 (7)	0.0001 (6)	−0.0001 (6)
C14	0.0230 (8)	0.0162 (8)	0.0200 (7)	0.0024 (7)	−0.0019 (6)	−0.0026 (6)
C15	0.0280 (9)	0.0186 (8)	0.0182 (8)	0.0013 (7)	0.0019 (6)	0.0015 (6)
C16	0.0271 (9)	0.0190 (8)	0.0186 (8)	0.0000 (7)	−0.0001 (6)	0.0024 (6)
C17	0.0285 (9)	0.0185 (8)	0.0198 (8)	0.0002 (7)	−0.0009 (6)	−0.0003 (6)
C18	0.0266 (9)	0.0218 (8)	0.0212 (8)	0.0004 (7)	0.0004 (6)	0.0002 (7)
C19	0.0259 (8)	0.0179 (8)	0.0220 (8)	−0.0006 (7)	0.0025 (6)	−0.0043 (6)
C20	0.0274 (9)	0.0210 (8)	0.0228 (8)	0.0024 (7)	−0.0004 (7)	−0.0017 (6)
C21	0.0278 (9)	0.0244 (9)	0.0247 (8)	0.0020 (7)	−0.0013 (7)	−0.0062 (7)
C22	0.0384 (10)	0.0209 (9)	0.0306 (9)	0.0025 (8)	−0.0061 (8)	−0.0100 (7)
C23	0.0354 (10)	0.0175 (8)	0.0311 (9)	0.0039 (7)	−0.0051 (7)	−0.0039 (7)
C24	0.0263 (8)	0.0213 (8)	0.0214 (8)	−0.0015 (7)	−0.0004 (6)	−0.0019 (6)
C25	0.0300 (9)	0.0156 (8)	0.0251 (8)	−0.0001 (7)	0.0020 (7)	−0.0015 (6)
C26	0.0314 (9)	0.0163 (8)	0.0243 (8)	−0.0020 (7)	0.0015 (7)	0.0011 (6)
C27	0.0271 (9)	0.0211 (8)	0.0203 (8)	0.0009 (7)	0.0001 (6)	0.0004 (6)
C28	0.0365 (10)	0.0219 (9)	0.0283 (9)	−0.0067 (8)	−0.0015 (7)	0.0037 (7)
C29	0.0359 (10)	0.0275 (9)	0.0225 (8)	−0.0015 (8)	0.0010 (7)	0.0076 (7)
C30	0.0259 (8)	0.0255 (9)	0.0202 (8)	0.0054 (7)	0.0014 (6)	−0.0001 (7)
C31	0.0251 (8)	0.0192 (8)	0.0232 (8)	0.0006 (7)	0.0002 (6)	−0.0013 (6)
C32	0.0254 (8)	0.0191 (8)	0.0194 (8)	0.0030 (7)	0.0013 (6)	0.0002 (6)
C33	0.0269 (9)	0.0186 (8)	0.0215 (8)	−0.0006 (7)	−0.0021 (6)	−0.0030 (7)
C34	0.0289 (9)	0.0188 (8)	0.0221 (8)	−0.0002 (7)	−0.0011 (7)	−0.0025 (7)
C35	0.0292 (9)	0.0192 (8)	0.0211 (8)	−0.0002 (7)	0.0002 (7)	−0.0016 (6)
C36	0.0267 (9)	0.0196 (8)	0.0221 (8)	−0.0008 (7)	−0.0001 (7)	−0.0035 (7)
C37	0.0373 (10)	0.0342 (10)	0.0188 (8)	−0.0040 (8)	0.0036 (7)	−0.0022 (7)
C38	0.0444 (11)	0.0346 (11)	0.0346 (10)	−0.0041 (9)	0.0157 (8)	−0.0031 (8)
C39	0.0608 (13)	0.0367 (11)	0.0358 (10)	−0.0074 (10)	0.0218 (9)	−0.0126 (8)
C40	0.0319 (9)	0.0263 (9)	0.0203 (8)	0.0034 (8)	0.0017 (7)	−0.0054 (7)
C41	0.0420 (11)	0.0312 (10)	0.0216 (8)	0.0035 (8)	0.0060 (7)	0.0005 (7)
C42	0.0346 (10)	0.0300 (10)	0.0278 (9)	0.0053 (8)	0.0055 (7)	−0.0044 (7)
C43	0.0375 (10)	0.0329 (10)	0.0245 (9)	0.0040 (8)	−0.0054 (7)	−0.0093 (7)
C44	0.0410 (11)	0.0415 (11)	0.0251 (9)	0.0019 (9)	−0.0056 (8)	−0.0020 (8)
C45	0.0453 (11)	0.0364 (11)	0.0356 (10)	−0.0001 (9)	−0.0124 (9)	−0.0080 (8)
C46	0.0348 (10)	0.0362 (10)	0.0172 (8)	0.0052 (8)	−0.0012 (7)	−0.0009 (7)
C47	0.0482 (12)	0.0394 (11)	0.0299 (10)	−0.0024 (9)	−0.0119 (8)	−0.0046 (8)
C48	0.0526 (14)	0.0865 (18)	0.0347 (11)	0.0291 (13)	−0.0175 (10)	−0.0187 (11)

Geometric parameters (Å, º) top

C1—C2	1.403 (2)	C29—C30	1.394 (2)
C1—C6	1.409 (2)	C29—H29	0.95
C1—C36	1.434 (2)	C30—C31	1.390 (2)
C2—C3	1.391 (2)	C30—C46	1.520 (2)
C2—H2	0.95	C31—C32	1.403 (2)
C3—C4	1.394 (2)	C31—H31	0.95
C3—C37	1.521 (2)	C32—C33	1.432 (2)
C4—C5	1.380 (2)	C33—C34	1.204 (2)
C4—H4	0.95	C34—C35	1.377 (2)
C5—C6	1.398 (2)	C35—C36	1.205 (2)
C5—H5	0.95	C37—C39	1.517 (3)
C6—C7	1.436 (2)	C37—C38	1.528 (2)
C7—C8	1.204 (2)	C37—H37	1
C8—C9	1.433 (2)	C38—H38A	0.98
C9—C10	1.398 (2)	C38—H38B	0.98
C9—C14	1.408 (2)	C38—H38C	0.98
C10—C11	1.386 (2)	C39—H39A	0.98
C10—H10	0.95	C39—H39B	0.98
C11—C12	1.394 (2)	C39—H39C	0.98
C11—H11	0.95	C40—C42	1.520 (2)
C12—C13	1.388 (2)	C40—C41	1.523 (2)
C12—C40	1.521 (2)	C40—H40	1
C13—C14	1.399 (2)	C41—H41A	0.98
C13—H13	0.95	C41—H41B	0.98
C14—C15	1.429 (2)	C41—H41C	0.98
C15—C16	1.206 (2)	C42—H42A	0.98
C16—C17	1.370 (2)	C42—H42B	0.98
C17—C18	1.204 (2)	C42—H42C	0.98
C18—C19	1.430 (2)	C43—C44	1.524 (2)
C19—C20	1.402 (2)	C43—C45	1.530 (3)
C19—C24	1.409 (2)	C43—H43	1
C20—C21	1.386 (2)	C44—H44A	0.98
C20—H20	0.95	C44—H44B	0.98
C21—C22	1.398 (2)	C44—H44C	0.98
C21—C43	1.526 (2)	C45—H45A	0.98
C22—C23	1.381 (2)	C45—H45B	0.98
C22—H22	0.95	C45—H45C	0.98
C23—C24	1.398 (2)	C46—C47	1.510 (2)
C23—H23	0.95	C46—C48	1.517 (3)
C24—C25	1.436 (2)	C46—H46	1
C25—C26	1.203 (2)	C47—H47A	0.98
C26—C27	1.433 (2)	C47—H47B	0.98
C27—C28	1.396 (2)	C47—H47C	0.98
C27—C32	1.415 (2)	C48—H48A	0.98
C28—C29	1.383 (2)	C48—H48B	0.98
C28—H28	0.95	C48—H48C	0.98

C2—C1—C6	119.60 (13)	C31—C32—C33	120.00 (14)
C2—C1—C36	120.68 (14)	C27—C32—C33	120.34 (13)
C6—C1—C36	119.71 (13)	C34—C33—C32	179.17 (18)
C3—C2—C1	121.45 (15)	C33—C34—C35	177.59 (18)
C3—C2—H2	119.3	C36—C35—C34	177.59 (18)
C1—C2—H2	119.3	C35—C36—C1	177.89 (17)
C2—C3—C4	117.98 (14)	C39—C37—C3	114.04 (14)
C2—C3—C37	122.91 (15)	C39—C37—C38	111.02 (15)
C4—C3—C37	119.06 (14)	C3—C37—C38	109.82 (13)
C5—C4—C3	121.64 (14)	C39—C37—H37	107.2
C5—C4—H4	119.2	C3—C37—H37	107.2
C3—C4—H4	119.2	C38—C37—H37	107.2
C4—C5—C6	120.69 (15)	C37—C38—H38A	109.5
C4—C5—H5	119.7	C37—C38—H38B	109.5
C6—C5—H5	119.7	H38A—C38—H38B	109.5
C5—C6—C1	118.62 (14)	C37—C38—H38C	109.5
C5—C6—C7	121.42 (14)	H38A—C38—H38C	109.5
C1—C6—C7	119.95 (13)	H38B—C38—H38C	109.5
C8—C7—C6	176.25 (16)	C37—C39—H39A	109.5
C7—C8—C9	175.33 (17)	C37—C39—H39B	109.5
C10—C9—C14	118.40 (14)	H39A—C39—H39B	109.5
C10—C9—C8	121.83 (14)	C37—C39—H39C	109.5
C14—C9—C8	119.70 (14)	H39A—C39—H39C	109.5
C11—C10—C9	120.41 (15)	H39B—C39—H39C	109.5
C11—C10—H10	119.8	C42—C40—C12	110.63 (13)
C9—C10—H10	119.8	C42—C40—C41	110.00 (14)
C10—C11—C12	121.90 (14)	C12—C40—C41	114.63 (13)
C10—C11—H11	119	C42—C40—H40	107.1
C12—C11—H11	119	C12—C40—H40	107.1
C13—C12—C11	117.63 (14)	C41—C40—H40	107.1
C13—C12—C40	122.84 (14)	C40—C41—H41A	109.5
C11—C12—C40	119.53 (14)	C40—C41—H41B	109.5
C12—C13—C14	121.67 (14)	H41A—C41—H41B	109.5
C12—C13—H13	119.2	C40—C41—H41C	109.5
C14—C13—H13	119.2	H41A—C41—H41C	109.5
C13—C14—C9	119.93 (14)	H41B—C41—H41C	109.5
C13—C14—C15	119.39 (14)	C40—C42—H42A	109.5
C9—C14—C15	120.64 (13)	C40—C42—H42B	109.5
C16—C15—C14	178.34 (17)	H42A—C42—H42B	109.5
C15—C16—C17	178.73 (18)	C40—C42—H42C	109.5
C18—C17—C16	178.88 (18)	H42A—C42—H42C	109.5
C17—C18—C19	178.44 (17)	H42B—C42—H42C	109.5
C20—C19—C24	120.06 (14)	C44—C43—C21	114.14 (14)
C20—C19—C18	120.17 (14)	C44—C43—C45	110.55 (15)
C24—C19—C18	119.78 (13)	C21—C43—C45	110.78 (14)
C21—C20—C19	121.53 (15)	C44—C43—H43	107
C21—C20—H20	119.2	C21—C43—H43	107
C19—C20—H20	119.2	C45—C43—H43	107
C20—C21—C22	117.49 (14)	C43—C44—H44A	109.5
C20—C21—C43	122.80 (15)	C43—C44—H44B	109.5
C22—C21—C43	119.72 (14)	H44A—C44—H44B	109.5
C23—C22—C21	122.16 (15)	C43—C44—H44C	109.5
C23—C22—H22	118.9	H44A—C44—H44C	109.5
C21—C22—H22	118.9	H44B—C44—H44C	109.5
C22—C23—C24	120.46 (15)	C43—C45—H45A	109.5
C22—C23—H23	119.8	C43—C45—H45B	109.5
C24—C23—H23	119.8	H45A—C45—H45B	109.5
C23—C24—C19	118.25 (14)	C43—C45—H45C	109.5
C23—C24—C25	122.27 (15)	H45A—C45—H45C	109.5
C19—C24—C25	119.44 (14)	H45B—C45—H45C	109.5
C26—C25—C24	174.43 (17)	C47—C46—C48	110.17 (17)
C25—C26—C27	176.80 (17)	C47—C46—C30	114.42 (14)
C28—C27—C32	118.09 (14)	C48—C46—C30	109.62 (14)
C28—C27—C26	121.65 (15)	C47—C46—H46	107.5
C32—C27—C26	120.24 (14)	C48—C46—H46	107.5
C29—C28—C27	121.18 (15)	C30—C46—H46	107.5
C29—C28—H28	119.4	C46—C47—H47A	109.5
C27—C28—H28	119.4	C46—C47—H47B	109.5
C28—C29—C30	121.52 (15)	H47A—C47—H47B	109.5
C28—C29—H29	119.2	C46—C47—H47C	109.5
C30—C29—H29	119.2	H47A—C47—H47C	109.5
C31—C30—C29	117.81 (14)	H47B—C47—H47C	109.5
C31—C30—C46	122.41 (15)	C46—C48—H48A	109.5
C29—C30—C46	119.65 (14)	C46—C48—H48B	109.5
C30—C31—C32	121.73 (15)	H48A—C48—H48B	109.5
C30—C31—H31	119.1	C46—C48—H48C	109.5
C32—C31—H31	119.1	H48A—C48—H48C	109.5
C31—C32—C27	119.64 (14)	H48B—C48—H48C	109.5

C6—C1—C2—C3	0.4 (2)	C22—C23—C24—C25	−175.30 (16)
C36—C1—C2—C3	−178.54 (15)	C20—C19—C24—C23	−1.3 (2)
C1—C2—C3—C4	−1.7 (2)	C18—C19—C24—C23	179.13 (15)
C1—C2—C3—C37	175.55 (15)	C20—C19—C24—C25	176.40 (15)
C2—C3—C4—C5	1.8 (2)	C18—C19—C24—C25	−3.2 (2)
C37—C3—C4—C5	−175.55 (15)	C32—C27—C28—C29	1.5 (2)
C3—C4—C5—C6	−0.6 (2)	C26—C27—C28—C29	−176.98 (16)
C4—C5—C6—C1	−0.7 (2)	C27—C28—C29—C30	−0.2 (3)
C4—C5—C6—C7	−179.51 (15)	C28—C29—C30—C31	−0.7 (2)
C2—C1—C6—C5	0.8 (2)	C28—C29—C30—C46	−176.65 (15)
C36—C1—C6—C5	179.77 (14)	C29—C30—C31—C32	0.3 (2)
C2—C1—C6—C7	179.63 (14)	C46—C30—C31—C32	176.14 (14)
C36—C1—C6—C7	−1.4 (2)	C30—C31—C32—C27	1.0 (2)
C14—C9—C10—C11	2.2 (2)	C30—C31—C32—C33	−177.81 (15)
C8—C9—C10—C11	−174.65 (15)	C28—C27—C32—C31	−1.9 (2)
C9—C10—C11—C12	−1.1 (3)	C26—C27—C32—C31	176.64 (15)
C10—C11—C12—C13	−1.1 (2)	C28—C27—C32—C33	176.94 (15)
C10—C11—C12—C40	178.95 (15)	C26—C27—C32—C33	−4.5 (2)
C11—C12—C13—C14	2.1 (2)	C2—C3—C37—C39	14.4 (2)
C40—C12—C13—C14	−177.86 (14)	C4—C3—C37—C39	−168.35 (16)
C12—C13—C14—C9	−1.0 (2)	C2—C3—C37—C38	−110.89 (18)
C12—C13—C14—C15	177.02 (14)	C4—C3—C37—C38	66.3 (2)
C10—C9—C14—C13	−1.2 (2)	C13—C12—C40—C42	−115.35 (17)
C8—C9—C14—C13	175.78 (14)	C11—C12—C40—C42	64.6 (2)
C10—C9—C14—C15	−179.21 (14)	C13—C12—C40—C41	9.7 (2)
C8—C9—C14—C15	−2.3 (2)	C11—C12—C40—C41	−170.28 (15)
C24—C19—C20—C21	−0.8 (2)	C20—C21—C43—C44	10.6 (2)
C18—C19—C20—C21	178.76 (15)	C22—C21—C43—C44	−169.67 (16)
C19—C20—C21—C22	1.8 (2)	C20—C21—C43—C45	−114.94 (18)
C19—C20—C21—C43	−178.43 (15)	C22—C21—C43—C45	64.8 (2)
C20—C21—C22—C23	−0.8 (3)	C31—C30—C46—C47	36.4 (2)
C43—C21—C22—C23	179.47 (16)	C29—C30—C46—C47	−147.78 (16)
C21—C22—C23—C24	−1.3 (3)	C31—C30—C46—C48	−87.9 (2)
C22—C23—C24—C19	2.3 (2)	C29—C30—C46—C48	87.9 (2)

Experimental details

Crystal data
Chemical formula	C₄₈H₄₀
M_r	616.8
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	90
a, b, c (Å)	18.0007 (4), 12.5083 (3), 16.0674 (4)
β (°)	91.004 (1)
V (Å³)	3617.15 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.06
Crystal size (mm)	0.45 × 0.30 × 0.30

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor 1997)
T_min, T_max	0.972, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	13998, 8186, 5354
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.680

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.127, 1.02
No. of reflections	8186
No. of parameters	442
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.28

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), IDEAL (Gould et al., 1988) and WinGX (Farrugia, 1999).

Footnotes

¹CAS 186494-88-2.

Acknowledgements

The purchase of the diffractometer was made possible by Grant No. LEQSF(1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents. We are grateful to Professor Adam Matzger for providing the sample.

References

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