Phen­yl(2,4,5-triphenyl­cyclo­penta-1,4-dien-1-yl)methanone

Cordes, D.B.; Hua, G.; Slawin, A.M.Z.; Woollins, J.D.

doi:10.1107/S1600536811022902

organic compounds

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Volume 67| Part 7| July 2011| Page o1718

doi:10.1107/S1600536811022902

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Phenyl(2,4,5-triphenylcyclopenta-1,4-dien-1-yl)methanone

David B. Cordes,^a Guoxiong Hua,^a Alexandra M. Z. Slawin ^a ^* and J. Derek Woollins ^a

^aSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
^*Correspondence e-mail: amzs@st-andrews.ac.uk

(Received 27 May 2011; accepted 13 June 2011; online 18 June 2011)

The title compound, C₃₀H₂₂O, does not form face-to-face π–π interactions despite the presence of four phenyl rings within the compound. Instead weak C—H⋯π interactions occur between adjacent molecules, with C⋯C contact distances in the range 3.633 (4)–3.974 (4) Å. The ketone O atom also takes part in a weak C—H⋯O interaction. The three pendant phenyl rings are twisted relative to the central cyclopentadiene ring by 17.82 (17), 29.63 (14) and 61.57 (9)°, while the phenylmethanone is nearly orthogonal, the angle between planes being 87.77 (9)°.

Related literature

For a previous preparation of the title compound, see: Lund (2005 ). The crystal studied was obtained by reaction of Woollins' reagent [2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide] with quinoxaline-2,3-dithiol. For a review of the chemistry of Woollins' reagent, see: Hua & Woollins (2009 ). There are no structurally closely-related compounds in the literature; however, for some of the closest related, see: Evrard et al. (1971 ); Wender et al. (2006 ).

Experimental

Crystal data

C₃₀H₂₂O
M_r = 398.48
Monoclinic, C 2/c
a = 25.946 (6) Å
b = 6.1573 (14) Å
c = 26.602 (6) Å
β = 102.236 (7)°
V = 4153.3 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 93 K
0.30 × 0.20 × 0.06 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010 ) T_min = 0.978, T_max = 0.996
13266 measured reflections
4252 independent reflections
2479 reflections with I > 2σ(I)
R_int = 0.120

Refinement

R[F² > 2σ(F²)] = 0.081
wR(F²) = 0.225
S = 1.04
4252 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C6–C11 and C25–C30 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O1ⁱ	0.99	2.64	3.229 (3)	118 (2)
C10—H10⋯Cg1ⁱⁱ	0.95	2.80	3.527 (3)	134 (2)
C20—H20⋯Cg2ⁱⁱⁱ	0.95	2.80	3.605 (3)	143 (2)
C28—H28⋯Cg1^iv	0.95	2.88	3.612 (3)	134 (2)
Symmetry codes: (i) x, y+1, z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z; (iv) $[-x+1, y+1, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2010); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811022902/fj2426sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022902/fj2426Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811022902/fj2426Isup3.cml

checkCIF report

Comment top

The previously know title compound (Lund, 2005) has been prepared by the reaction of Woollins' reagent with quinoxaline-2,3-dithiol. In a similar manner to the two somewhat related structures (Evrard et al., 1971 and Wender et al., 2006) no face-to-face π-interactions are observed, adjacent molecules instead interacting via a series of CH···π interactions. The ketone oxygen makes intermolecular CH···O contacts at a distance of 2.64 Å.

Related literature top

For a previous preparation of the title compound, see: Lund (2005). For a review of the other chemistry of Woollins' reagent, 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide, see: Hua & Woollins (2009). There are no structurally closely-related compounds in the literature; however, for some of the closest related, see: Evrard et al. (1971); Wender et al. (2006).

Experimental top

A mixture of 0.194 g of quinoxaline-2,3-dithiol (1.0 mmol) and Woollins' reagent (0.54 g, 1.0 mmol) in 20 ml of dry toluene was refluxed for 7 h. The red suspension disappeared and a deep red solution formed. Following cooling to room temperature and removal of solvent in vacuuo the residue was purified by silica gel column chromatography (1: 1 hexane/dichloromethane eluent) to give the title compound as a brown solid (0.060 g, 13%). Crystals suitable for X-ray structure determination were obtained from the diffusion of hexane into a dichloromethane solution of the title compound. Selected IR (KBr, cm^-1): 1658(s, C═O), 1596(m), 1490(m), 1443(m), 1243(s), 754(s), 6932(versus). ¹H NMR (CD₂Cl₂, δ), 8.13–8.00 (m, 2H, ArH), 7.93–7.83 (m, 3H, ArH), 7.61–6.92 (m, 15H, ArH), 4.24 (s, 2H, CH₂) p.p.m.. ¹³C NMR (CD₂Cl₂, δ), 168.5 (C═O), 144.0, 135.8, 134.4, 133.4, 132.6, 130.7, 129.8, 129.4, 129.2, 129.0, 128.9, 128.8, 128.5, 128.3, 128.1, 127.9, 127.6, 127.4, 127.2, 127.0, 126.6, 46.0 p.p.m.. MS (CI⁺, m/z), 399 [M+H]⁺. Accurate mass measurement [CI⁺, m/z]: 399.1737 [M+H]⁺, calculated mass for C₃₀H₂₃O: 399.1743.

Computing details top

Data collection: CrystalClear (Rigaku, 2010); cell refinement: CrystalClear (Rigaku, 2010); data reduction: CrystalClear (Rigaku, 2010); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

phenyl(2,4,5-triphenylcyclopenta-1,4-dien-1-yl)methanone top

Crystal data top

C₃₀H₂₂O	F(000) = 1680
M_r = 398.48	D_x = 1.275 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3958 reflections
a = 25.946 (6) Å	θ = 6.3–54.9°
b = 6.1573 (14) Å	µ = 0.08 mm⁻¹
c = 26.602 (6) Å	T = 93 K
β = 102.236 (7)°	Prism, colourless
V = 4153.3 (16) Å³	0.30 × 0.20 × 0.06 mm
Z = 8

Data collection top

Rigaku Mercury CCD diffractometer	4252 independent reflections
Radiation source: rotating anode	2479 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.120
Detector resolution: 14.7059 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω and ϕ scans	h = −33→26
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010)	k = −7→7
T_min = 0.978, T_max = 0.996	l = −28→33
13266 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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.225	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1072P)²] where P = (F_o² + 2F_c²)/3
4252 reflections	(Δ/σ)_max < 0.001
281 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₃₀H₂₂O	V = 4153.3 (16) Å³
M_r = 398.48	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.946 (6) Å	µ = 0.08 mm⁻¹
b = 6.1573 (14) Å	T = 93 K
c = 26.602 (6) Å	0.30 × 0.20 × 0.06 mm
β = 102.236 (7)°

Data collection top

Rigaku Mercury CCD diffractometer	4252 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010)	2479 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.996	R_int = 0.120
13266 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	0 restraints
wR(F²) = 0.225	H-atom parameters constrained
S = 1.04	Δρ_max = 0.29 e Å⁻³
4252 reflections	Δρ_min = −0.39 e Å⁻³
281 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.

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
O1	0.36026 (8)	0.0838 (4)	0.13591 (8)	0.0494 (6)
C1	0.41982 (10)	0.7166 (5)	0.21370 (9)	0.0300 (7)
H1A	0.4480	0.6866	0.2443	0.036*
H1B	0.4032	0.8577	0.2185	0.036*
C2	0.37945 (10)	0.5375 (4)	0.20539 (9)	0.0279 (7)
C3	0.37812 (10)	0.4503 (4)	0.15812 (9)	0.0289 (7)
C4	0.41591 (10)	0.5655 (4)	0.13312 (9)	0.0283 (7)
C5	0.44176 (10)	0.7189 (4)	0.16562 (9)	0.0269 (6)
C6	0.34825 (10)	0.4843 (5)	0.24389 (10)	0.0304 (7)
C7	0.34567 (11)	0.6341 (5)	0.28290 (10)	0.0368 (7)
H7	0.3645	0.7672	0.2842	0.044*
C8	0.31633 (12)	0.5923 (6)	0.31959 (11)	0.0454 (8)
H8	0.3153	0.6964	0.3457	0.054*
C9	0.28875 (12)	0.4015 (6)	0.31855 (11)	0.0452 (8)
H9	0.2681	0.3746	0.3434	0.054*
C10	0.29138 (11)	0.2480 (5)	0.28080 (12)	0.0434 (8)
H10	0.2730	0.1144	0.2803	0.052*
C11	0.32083 (10)	0.2887 (5)	0.24366 (11)	0.0350 (7)
H11	0.3223	0.1828	0.2180	0.042*
C12	0.34422 (11)	0.2708 (5)	0.13193 (10)	0.0315 (7)
C13	0.29162 (11)	0.3222 (5)	0.09964 (10)	0.0313 (7)
C14	0.26130 (11)	0.1535 (5)	0.07379 (10)	0.0374 (7)
H14	0.2746	0.0093	0.0765	0.045*
C15	0.21138 (11)	0.1970 (5)	0.04388 (11)	0.0416 (8)
H15	0.1906	0.0819	0.0265	0.050*
C16	0.19237 (12)	0.4045 (6)	0.03957 (12)	0.0516 (9)
H16	0.1584	0.4337	0.0191	0.062*
C17	0.22223 (14)	0.5704 (6)	0.06479 (16)	0.0740 (13)
H17	0.2090	0.7148	0.0615	0.089*
C18	0.27205 (12)	0.5288 (5)	0.09539 (12)	0.0522 (10)
H18	0.2923	0.6443	0.1132	0.063*
C19	0.42011 (10)	0.5280 (5)	0.07848 (9)	0.0291 (7)
C20	0.43588 (10)	0.3314 (5)	0.06182 (10)	0.0341 (7)
H20	0.4437	0.2132	0.0852	0.041*
C21	0.44040 (11)	0.3058 (5)	0.01114 (11)	0.0397 (8)
H21	0.4518	0.1709	0.0000	0.048*
C22	0.42837 (11)	0.4765 (5)	−0.02322 (11)	0.0398 (8)
H22	0.4315	0.4583	−0.0579	0.048*
C23	0.41199 (11)	0.6712 (5)	−0.00742 (10)	0.0380 (8)
H23	0.4035	0.7875	−0.0312	0.046*
C24	0.40768 (11)	0.6993 (5)	0.04363 (10)	0.0358 (7)
H24	0.3963	0.8346	0.0546	0.043*
C25	0.48404 (10)	0.8684 (4)	0.15913 (9)	0.0271 (7)
C26	0.52110 (10)	0.8136 (5)	0.12983 (10)	0.0336 (7)
H26	0.5184	0.6775	0.1127	0.040*
C27	0.56144 (11)	0.9533 (5)	0.12544 (10)	0.0381 (8)
H27	0.5859	0.9127	0.1051	0.046*
C28	0.56674 (11)	1.1516 (5)	0.15023 (11)	0.0392 (8)
H28	0.5946	1.2473	0.1471	0.047*
C29	0.53077 (11)	1.2092 (5)	0.17984 (11)	0.0373 (8)
H29	0.5341	1.3447	0.1973	0.045*
C30	0.49004 (11)	1.0692 (5)	0.18395 (9)	0.0317 (7)
H30	0.4656	1.1110	0.2042	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0409 (12)	0.0385 (14)	0.0614 (14)	0.0034 (10)	−0.0057 (11)	−0.0054 (11)
C1	0.0278 (15)	0.0406 (18)	0.0201 (14)	0.0017 (12)	0.0013 (11)	0.0012 (11)
C2	0.0215 (14)	0.0374 (18)	0.0244 (15)	0.0014 (11)	0.0041 (11)	0.0016 (11)
C3	0.0221 (14)	0.0344 (17)	0.0271 (15)	0.0022 (11)	−0.0017 (11)	0.0006 (12)
C4	0.0243 (14)	0.0341 (17)	0.0251 (14)	0.0014 (11)	0.0019 (11)	0.0019 (12)
C5	0.0227 (14)	0.0343 (17)	0.0223 (14)	0.0008 (11)	0.0016 (11)	0.0032 (11)
C6	0.0197 (14)	0.0410 (18)	0.0280 (15)	0.0001 (12)	−0.0003 (11)	0.0011 (12)
C7	0.0349 (17)	0.048 (2)	0.0280 (15)	−0.0041 (14)	0.0078 (13)	−0.0019 (13)
C8	0.047 (2)	0.057 (2)	0.0338 (17)	−0.0068 (16)	0.0134 (14)	−0.0049 (15)
C9	0.0383 (18)	0.068 (2)	0.0318 (17)	−0.0027 (16)	0.0139 (14)	0.0047 (16)
C10	0.0355 (18)	0.053 (2)	0.0419 (18)	−0.0084 (15)	0.0078 (14)	0.0089 (16)
C11	0.0307 (16)	0.0411 (19)	0.0337 (16)	−0.0035 (13)	0.0079 (13)	−0.0009 (13)
C12	0.0314 (16)	0.0336 (18)	0.0300 (15)	0.0018 (13)	0.0079 (12)	0.0020 (12)
C13	0.0323 (16)	0.0339 (17)	0.0270 (15)	0.0001 (12)	0.0044 (12)	−0.0020 (12)
C14	0.0387 (17)	0.0398 (19)	0.0317 (16)	−0.0051 (14)	0.0031 (13)	−0.0001 (13)
C15	0.0395 (18)	0.048 (2)	0.0330 (17)	−0.0103 (15)	−0.0032 (13)	−0.0044 (14)
C16	0.0402 (19)	0.054 (2)	0.050 (2)	0.0045 (16)	−0.0141 (15)	−0.0040 (17)
C17	0.055 (2)	0.047 (2)	0.097 (3)	0.0130 (18)	−0.034 (2)	−0.014 (2)
C18	0.0411 (19)	0.040 (2)	0.063 (2)	0.0018 (15)	−0.0173 (16)	−0.0145 (16)
C19	0.0254 (14)	0.0352 (18)	0.0242 (14)	−0.0018 (12)	−0.0003 (11)	−0.0022 (12)
C20	0.0331 (16)	0.0387 (19)	0.0277 (16)	0.0003 (13)	0.0001 (12)	−0.0043 (12)
C21	0.0349 (17)	0.045 (2)	0.0384 (18)	0.0007 (14)	0.0064 (14)	−0.0093 (14)
C22	0.0372 (17)	0.054 (2)	0.0269 (15)	−0.0033 (15)	0.0041 (13)	−0.0038 (14)
C23	0.0385 (17)	0.049 (2)	0.0253 (16)	−0.0016 (14)	0.0041 (13)	0.0006 (13)
C24	0.0344 (16)	0.0428 (19)	0.0273 (16)	0.0032 (13)	0.0000 (12)	−0.0018 (13)
C25	0.0233 (14)	0.0365 (17)	0.0191 (14)	0.0002 (12)	−0.0010 (11)	0.0034 (11)
C26	0.0308 (16)	0.0416 (19)	0.0273 (15)	−0.0013 (13)	0.0039 (12)	−0.0029 (12)
C27	0.0331 (17)	0.050 (2)	0.0319 (16)	−0.0055 (14)	0.0086 (13)	0.0022 (14)
C28	0.0299 (17)	0.051 (2)	0.0323 (17)	−0.0089 (14)	−0.0022 (13)	0.0075 (14)
C29	0.0334 (17)	0.0406 (19)	0.0330 (16)	−0.0055 (13)	−0.0046 (13)	−0.0018 (13)
C30	0.0335 (16)	0.0411 (19)	0.0178 (13)	0.0022 (13)	−0.0005 (11)	0.0025 (12)

Geometric parameters (Å, º) top

O1—C12	1.221 (3)	C15—H15	0.9500
C1—C2	1.504 (4)	C16—C17	1.369 (5)
C1—C5	1.506 (4)	C16—H16	0.9500
C1—H1A	0.9900	C17—C18	1.398 (4)
C1—H1B	0.9900	C17—H17	0.9500
C2—C3	1.361 (4)	C18—H18	0.9500
C2—C6	1.471 (4)	C19—C20	1.381 (4)
C3—C4	1.478 (4)	C19—C24	1.396 (4)
C3—C12	1.490 (4)	C20—C21	1.387 (4)
C4—C5	1.358 (3)	C20—H20	0.9500
C4—C19	1.498 (4)	C21—C22	1.384 (4)
C5—C25	1.470 (4)	C21—H21	0.9500
C6—C11	1.398 (4)	C22—C23	1.367 (4)
C6—C7	1.401 (4)	C22—H22	0.9500
C7—C8	1.383 (4)	C23—C24	1.397 (4)
C7—H7	0.9500	C23—H23	0.9500
C8—C9	1.372 (4)	C24—H24	0.9500
C8—H8	0.9500	C25—C30	1.395 (4)
C9—C10	1.392 (4)	C25—C26	1.401 (4)
C9—H9	0.9500	C26—C27	1.379 (4)
C10—C11	1.394 (4)	C26—H26	0.9500
C10—H10	0.9500	C27—C28	1.380 (4)
C11—H11	0.9500	C27—H27	0.9500
C12—C13	1.484 (4)	C28—C29	1.389 (4)
C13—C18	1.366 (4)	C28—H28	0.9500
C13—C14	1.393 (4)	C29—C30	1.386 (4)
C14—C15	1.395 (4)	C29—H29	0.9500
C14—H14	0.9500	C30—H30	0.9500
C15—C16	1.366 (4)

C2—C1—C5	105.0 (2)	C14—C15—H15	119.9
C2—C1—H1A	110.7	C15—C16—C17	120.0 (3)
C5—C1—H1A	110.7	C15—C16—H16	120.0
C2—C1—H1B	110.7	C17—C16—H16	120.0
C5—C1—H1B	110.7	C16—C17—C18	120.4 (3)
H1A—C1—H1B	108.8	C16—C17—H17	119.8
C3—C2—C6	130.2 (3)	C18—C17—H17	119.8
C3—C2—C1	107.8 (2)	C13—C18—C17	120.1 (3)
C6—C2—C1	122.0 (2)	C13—C18—H18	120.0
C2—C3—C4	109.7 (2)	C17—C18—H18	120.0
C2—C3—C12	128.4 (3)	C20—C19—C24	119.5 (3)
C4—C3—C12	121.9 (2)	C20—C19—C4	122.2 (2)
C5—C4—C3	109.4 (2)	C24—C19—C4	118.3 (2)
C5—C4—C19	126.7 (2)	C19—C20—C21	120.2 (3)
C3—C4—C19	123.7 (2)	C19—C20—H20	119.9
C4—C5—C25	129.9 (2)	C21—C20—H20	119.9
C4—C5—C1	108.0 (2)	C22—C21—C20	120.1 (3)
C25—C5—C1	122.1 (2)	C22—C21—H21	119.9
C11—C6—C7	117.8 (3)	C20—C21—H21	119.9
C11—C6—C2	122.9 (3)	C23—C22—C21	120.3 (3)
C7—C6—C2	119.2 (3)	C23—C22—H22	119.9
C8—C7—C6	121.3 (3)	C21—C22—H22	119.9
C8—C7—H7	119.3	C22—C23—C24	120.1 (3)
C6—C7—H7	119.3	C22—C23—H23	120.0
C9—C8—C7	120.5 (3)	C24—C23—H23	120.0
C9—C8—H8	119.7	C19—C24—C23	119.8 (3)
C7—C8—H8	119.7	C19—C24—H24	120.1
C8—C9—C10	119.4 (3)	C23—C24—H24	120.1
C8—C9—H9	120.3	C30—C25—C26	117.1 (2)
C10—C9—H9	120.3	C30—C25—C5	120.7 (2)
C9—C10—C11	120.5 (3)	C26—C25—C5	122.1 (2)
C9—C10—H10	119.8	C27—C26—C25	121.3 (3)
C11—C10—H10	119.8	C27—C26—H26	119.4
C10—C11—C6	120.5 (3)	C25—C26—H26	119.4
C10—C11—H11	119.8	C26—C27—C28	120.8 (3)
C6—C11—H11	119.8	C26—C27—H27	119.6
O1—C12—C13	120.4 (3)	C28—C27—H27	119.6
O1—C12—C3	120.1 (2)	C27—C28—C29	119.1 (3)
C13—C12—C3	119.4 (2)	C27—C28—H28	120.5
C18—C13—C14	119.5 (3)	C29—C28—H28	120.5
C18—C13—C12	121.8 (2)	C30—C29—C28	120.1 (3)
C14—C13—C12	118.7 (3)	C30—C29—H29	120.0
C13—C14—C15	119.8 (3)	C28—C29—H29	120.0
C13—C14—H14	120.1	C29—C30—C25	121.6 (3)
C15—C14—H14	120.1	C29—C30—H30	119.2
C16—C15—C14	120.2 (3)	C25—C30—H30	119.2
C16—C15—H15	119.9

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C6–C11 and C25–C30 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1ⁱ	0.99	2.64	3.229 (3)	118 (2)
C10—H10···Cg1ⁱⁱ	0.95	2.80	3.527 (3)	134 (2)
C20—H20···Cg2ⁱⁱⁱ	0.95	2.80	3.605 (3)	143 (2)
C28—H28···Cg1^iv	0.95	2.88	3.612 (3)	134 (2)
C10—H10···C10ⁱⁱ	0.95	3.06	3.908 (4)	150 (2)
C20—H20···C30ⁱⁱⁱ	0.95	2.79	3.633 (4)	148 (2)
C28—H28···C9^iv	0.95	3.12	3.974 (4)	151 (2)

Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, y−1, z; (iv) −x+1, y+1, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₀H₂₂O
M_r	398.48
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	93
a, b, c (Å)	25.946 (6), 6.1573 (14), 26.602 (6)
β (°)	102.236 (7)
V (Å³)	4153.3 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.06

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2010)
T_min, T_max	0.978, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	13266, 4252, 2479
R_int	0.120
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.225, 1.04
No. of reflections	4252
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.39

Computer programs: CrystalClear (Rigaku, 2010), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C6–C11 and C25–C30 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1ⁱ	0.99	2.64	3.229 (3)	118.3 (19)
C10—H10···Cg1ⁱⁱ	0.95	2.80	3.527 (3)	134 (2)
C20—H20···Cg2ⁱⁱⁱ	0.95	2.80	3.605 (3)	143 (2)
C28—H28···Cg1^iv	0.95	2.88	3.612 (3)	134 (2)

Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, y−1, z; (iv) −x+1, y+1, −z+1/2.

Acknowledgements

The authors are grateful to the University of St Andrews and the Engineering and Physical Science Research Council (EPSRC, UK) for financial support.

References

Evrard, G., Piret, P., Germain, G. & Van Meerssche, M. (1971). Acta Cryst. B27, 661–666. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Hua, G. & Woollins, J. D. (2009). Angew. Chem. Int. Ed. 48, 1368–1377. Web of Science CrossRef CAS Google Scholar
Lund, H. (2005). J. Electroanal. Chem. 584, 174–181. CrossRef CAS Google Scholar
Rigaku (2010). CrystalClear. Rigaku Americas, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wender, P. A., Paxton, T. J. & Williams, T. J. (2006). J. Am. Chem. Soc. 128, 14814–14815. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 67| Part 7| July 2011| Page o1718

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