Phen-yl(2,4,5-triphenyl-cyclo-penta-1,4-dien-1-yl)methanone.

The title compound, C(30)H(22)O, does not form face-to-face π-π inter-actions despite the presence of four phenyl rings within the compound. Instead weak C-H⋯π inter-actions occur between adjacent mol-ecules, 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 inter-action. 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 = 398.48

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.225

S = 1.04

4252 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.39 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811022902/fj2426sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811022902/fj2426Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C30H22O	F(000) = 1680
Mr = 398.48	Dx = 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

Rigaku Mercury CCD diffractometer	4252 independent reflections
Radiation source: rotating anode	2479 reflections with I > 2σ(I)
confocal	Rint = 0.120
Detector resolution: 14.7059 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω and φ scans	h = −33→26
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010)	k = −7→7
Tmin = 0.978, Tmax = 0.996	l = −28→33
13266 measured reflections

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(Fo2) + (0.1072P)2] where P = (Fo2 + 2Fc2)/3
4252 reflections	(Δ/σ)max < 0.001
281 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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···Cg1iv	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···C9iv	0.95	3.12	3.974 (4)	151 (2)

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⋯Cg1iv	0.95	2.88	3.612 (3)	134 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .