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The title compound, (I), crystallizes unsolvated in the triclinic space group P\overline 1, with one mol­ecule per unit cell and a centrosymmetric ababab conformation (a and b denote side-chain units projecting, respectively, above and below the plane of the aromatic core), which possesses non-crystallographic \overline 3 (S6) symmetry. The CH2 C atoms, in cyclic order, deviate from the mean plane of the central benzene ring by 0.042, -0.029, 0.050, -0.042, 0.029 and -0.050 Å (r.m.s. deviation 0.041 Å).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199016005/qa0192sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199016005/qa0192Isup2.hkl
Contains datablock I

CCDC reference: 140863

Comment top

No comment

Experimental top

The procedure employed Co2(CO)8 catalysed trimerization (cf., e.g., Schore, 1991) of 1,4-diphenylbut-2-yne which was prepared by a literature method (Dupont et al., 1954). Typically the acetylene (1 g, 4.9 mmol) was heated in a sealed tube under vacuum with Co2(CO)8 (0.1 g, 0.29 mmol) at 210°C for 3 h. The product was dissolved in chloroform, filtered and crystallized from this solvent, to give in near quantitative yield clear, colourless crystals (m.p. 580.5–581.5 K).

Refinement top

H atoms were placed geometrically and refined with a riding model with Uiso allowed to refine freely. Area-detector scaling and absorption corrections were performed by SADABS. This correction was used to scale the frames of data and to correct for absorption of the primary beam by the crystal support using the method of Blessing (1995). A correction for absorption of the primary beam by the crystal was not applied and as such the transmission factors quoted are not crystal dependant.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART and SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Sheldrick, 1999); program(s) used to refine structure: SHELXTL (Sheldrick, 1999); molecular graphics: SHELXTL (Sheldrick, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 1999).

(I) top
Crystal data top
C48H42F(000) = 330
Mr = 618.82Dx = 1.196 Mg m3
Triclinic, P1Melting point: 581 K
a = 8.999 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.456 (4) ÅCell parameters from 7886 reflections
c = 10.622 (4) Åθ = 2.1–29.0°
α = 69.218 (12)°µ = 0.07 mm1
β = 79.20 (2)°T = 123 K
γ = 67.07 (2)°Prism, colourless
V = 859.2 (5) Å30.45 × 0.35 × 0.30 mm
Z = 1
Data collection top
Bruker 1K CCD
diffractometer
3460 independent reflections
Radiation source: fine-focus sealed tube3077 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 8.192 pixels mm-1θmax = 26.4°, θmin = 2.1°
ω rotation with narrow frames scansh = 1111
Absorption correction: multi-scan
(Blessing, 1995)
k = 1313
Tmin = 0.970, Tmax = 1.000l = 1313
8524 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111Constrained (see text)
S = 1.01Calculated w = 1/[σ2(Fo2) + (0.065P)2 + 0.25P]
where P = (Fo2 + 2Fc2)/3
3460 reflections(Δ/σ)max = 0.001
238 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C48H42γ = 67.07 (2)°
Mr = 618.82V = 859.2 (5) Å3
Triclinic, P1Z = 1
a = 8.999 (2) ÅMo Kα radiation
b = 10.456 (4) ŵ = 0.07 mm1
c = 10.622 (4) ÅT = 123 K
α = 69.218 (12)°0.45 × 0.35 × 0.30 mm
β = 79.20 (2)°
Data collection top
Bruker 1K CCD
diffractometer
3460 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
3077 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 1.000Rint = 0.016
8524 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.111Constrained (see text)
S = 1.01Δρmax = 0.23 e Å3
3460 reflectionsΔρmin = 0.25 e Å3
238 parameters
Special details top

Experimental. The data collection nominally covered a sphere of reciprocal space, by a combination of four sets of exposures; each set had a different ϕ angle for the crystal and each exposure covered 0.3° in ω. The crystal-to-detector distance was 4.940 cm. Coverage of the unique set is 98.4% complete to 26.37° in θ. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analyzing the duplicate reflections.

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 on F2 for ALL reflections. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating observed R-factor. 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
xyzUiso*/Ueq
C10.10337 (13)0.60890 (11)0.90052 (11)0.0175 (2)
C20.06401 (13)0.57960 (11)0.88087 (11)0.0175 (2)
C30.16692 (12)0.47171 (11)0.98130 (11)0.0172 (2)
C40.21690 (13)0.72886 (12)0.79495 (11)0.0205 (2)
H4A0.16470.80130.74340.021 (3)*
H4B0.31630.77940.84200.026 (3)*
C50.26535 (14)0.67912 (12)0.69550 (11)0.0214 (2)
C60.16092 (14)0.56147 (13)0.65280 (12)0.0238 (3)
H6A0.05910.50530.69120.024 (3)*
C70.20429 (16)0.52524 (15)0.55426 (13)0.0306 (3)
H7A0.13120.44550.52520.038 (4)*
C80.35279 (17)0.60437 (18)0.49853 (13)0.0377 (3)
H8A0.38160.58030.43060.050 (5)*
C90.45902 (17)0.71912 (19)0.54286 (14)0.0417 (4)
H9A0.56230.77270.50640.051 (5)*
C100.41604 (15)0.75661 (15)0.64015 (13)0.0320 (3)
H10A0.49010.83590.66940.044 (4)*
C110.13380 (14)0.66425 (12)0.75129 (11)0.0209 (2)
H11A0.07000.68350.67590.025 (3)*
H11B0.24570.60160.73380.026 (3)*
C120.13691 (13)0.80916 (12)0.75059 (11)0.0206 (2)
C130.13827 (14)0.91764 (13)0.62769 (12)0.0264 (3)
H13A0.13120.90190.54660.035 (4)*
C140.14983 (16)1.04827 (14)0.62182 (14)0.0329 (3)
H14A0.15061.12090.53710.039 (4)*
C150.16028 (16)1.07299 (14)0.73909 (15)0.0339 (3)
H15A0.16871.16210.73520.043 (4)*
C160.15829 (17)0.96680 (14)0.86206 (14)0.0332 (3)
H16A0.16570.98310.94280.044 (4)*
C170.14549 (15)0.83617 (13)0.86801 (12)0.0267 (3)
H17A0.14260.76470.95310.032 (4)*
C180.34726 (13)0.44372 (12)0.96305 (11)0.0193 (2)
H18A0.38930.41091.05320.021 (3)*
H18B0.36290.53760.91180.025 (3)*
C190.44896 (13)0.33194 (12)0.89139 (11)0.0187 (2)
C200.59931 (14)0.33613 (13)0.83171 (13)0.0260 (3)
H20A0.63200.41280.83030.035 (4)*
C210.70214 (15)0.23011 (14)0.77424 (14)0.0316 (3)
H21A0.80470.23400.73470.041 (4)*
C220.65524 (16)0.11880 (13)0.77457 (13)0.0298 (3)
H22A0.72610.04530.73660.041 (4)*
C230.50464 (16)0.11490 (13)0.83048 (13)0.0279 (3)
H23A0.47150.03940.82950.037 (4)*
C240.40151 (14)0.22119 (13)0.88824 (12)0.0235 (3)
H24A0.29800.21820.92580.029 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0189 (5)0.0171 (5)0.0188 (5)0.0064 (4)0.0010 (4)0.0083 (4)
C20.0195 (5)0.0180 (5)0.0181 (5)0.0083 (4)0.0008 (4)0.0081 (4)
C30.0165 (5)0.0187 (5)0.0202 (5)0.0073 (4)0.0009 (4)0.0102 (4)
C40.0194 (5)0.0193 (5)0.0211 (5)0.0051 (4)0.0018 (4)0.0059 (4)
C50.0206 (5)0.0265 (6)0.0161 (5)0.0101 (4)0.0001 (4)0.0041 (4)
C60.0204 (6)0.0295 (6)0.0233 (6)0.0110 (5)0.0012 (4)0.0091 (5)
C70.0310 (6)0.0422 (7)0.0268 (6)0.0192 (6)0.0072 (5)0.0175 (5)
C80.0349 (7)0.0655 (10)0.0241 (6)0.0246 (7)0.0009 (5)0.0206 (6)
C90.0270 (7)0.0669 (10)0.0299 (7)0.0093 (7)0.0084 (5)0.0180 (7)
C100.0240 (6)0.0406 (7)0.0260 (6)0.0034 (5)0.0044 (5)0.0117 (5)
C110.0213 (5)0.0242 (5)0.0188 (5)0.0106 (4)0.0017 (4)0.0071 (4)
C120.0151 (5)0.0218 (5)0.0236 (6)0.0077 (4)0.0001 (4)0.0047 (4)
C130.0218 (6)0.0288 (6)0.0249 (6)0.0101 (5)0.0040 (4)0.0012 (5)
C140.0277 (6)0.0259 (6)0.0370 (7)0.0130 (5)0.0059 (5)0.0054 (5)
C150.0288 (7)0.0230 (6)0.0510 (8)0.0131 (5)0.0046 (6)0.0073 (6)
C160.0367 (7)0.0309 (7)0.0379 (7)0.0159 (6)0.0011 (6)0.0137 (6)
C170.0315 (6)0.0253 (6)0.0251 (6)0.0140 (5)0.0014 (5)0.0067 (5)
C180.0167 (5)0.0221 (5)0.0215 (5)0.0079 (4)0.0002 (4)0.0088 (4)
C190.0174 (5)0.0206 (5)0.0164 (5)0.0052 (4)0.0020 (4)0.0049 (4)
C200.0212 (6)0.0272 (6)0.0310 (6)0.0095 (5)0.0023 (5)0.0116 (5)
C210.0217 (6)0.0330 (7)0.0365 (7)0.0070 (5)0.0065 (5)0.0137 (5)
C220.0309 (7)0.0231 (6)0.0283 (6)0.0013 (5)0.0025 (5)0.0111 (5)
C230.0344 (7)0.0229 (6)0.0278 (6)0.0098 (5)0.0009 (5)0.0100 (5)
C240.0227 (6)0.0261 (6)0.0235 (6)0.0099 (5)0.0008 (4)0.0093 (5)
Geometric parameters (Å, º) top
C1—C3i1.4032 (16)C21—C221.3828 (19)
C1—C21.4051 (15)C22—C231.3839 (19)
C1—C41.5190 (16)C23—C241.3927 (17)
C2—C31.4036 (16)C4—H4A0.9900
C2—C111.5221 (15)C4—H4B0.9900
C3—C1i1.4032 (16)C6—H6A0.9500
C3—C181.5196 (14)C7—H7A0.9500
C4—C51.5217 (16)C8—H8A0.9500
C5—C61.3919 (17)C9—H9A0.9500
C5—C101.3949 (17)C10—H10A0.9500
C6—C71.3932 (17)C11—H11A0.9900
C7—C81.381 (2)C11—H11B0.9900
C8—C91.383 (2)C13—H13A0.9500
C9—C101.3880 (19)C14—H14A0.9500
C11—C121.5237 (16)C15—H15A0.9500
C12—C171.3944 (17)C16—H16A0.9500
C12—C131.3946 (17)C17—H17A0.9500
C13—C141.3886 (18)C18—H18A0.9900
C14—C151.385 (2)C18—H18B0.9900
C15—C161.384 (2)C20—H20A0.9500
C16—C171.3934 (18)C21—H21A0.9500
C18—C191.5230 (15)C22—H22A0.9500
C19—C201.3926 (16)C23—H23A0.9500
C19—C241.3938 (16)C24—H24A0.9500
C20—C211.3882 (17)
C3i—C1—C2120.10 (10)C5—C6—H6A119.7
C3i—C1—C4119.54 (10)C7—C6—H6A119.7
C2—C1—C4120.36 (10)C8—C7—H7A119.8
C3—C2—C1119.72 (10)C6—C7—H7A119.8
C3—C2—C11120.03 (10)C7—C8—H8A120.4
C1—C2—C11120.25 (10)C9—C8—H8A120.4
C1i—C3—C2120.16 (10)C8—C9—H9A119.7
C1i—C3—C18119.88 (10)C10—C9—H9A119.7
C2—C3—C18119.95 (10)C9—C10—H10A119.6
C1—C4—C5115.69 (9)C5—C10—H10A119.6
C6—C5—C10118.28 (11)C2—C11—H11A108.4
C6—C5—C4122.04 (10)C12—C11—H11A108.4
C10—C5—C4119.62 (11)C2—C11—H11B108.4
C5—C6—C7120.67 (11)C12—C11—H11B108.4
C8—C7—C6120.50 (12)H11A—C11—H11B107.5
C7—C8—C9119.23 (12)C14—C13—H13A119.4
C8—C9—C10120.57 (13)C12—C13—H13A119.4
C9—C10—C5120.73 (12)C15—C14—H14A119.9
C2—C11—C12115.52 (9)C13—C14—H14A119.9
C17—C12—C13118.11 (11)C16—C15—H15A120.3
C17—C12—C11122.63 (10)C14—C15—H15A120.3
C13—C12—C11119.20 (11)C15—C16—H16A119.8
C14—C13—C12121.13 (12)C17—C16—H16A119.8
C15—C14—C13120.18 (12)C16—C17—H17A119.6
C16—C15—C14119.48 (12)C12—C17—H17A119.6
C15—C16—C17120.34 (12)C3—C18—H18A108.2
C16—C17—C12120.76 (11)C19—C18—H18A108.2
C3—C18—C19116.33 (9)C3—C18—H18B108.2
C20—C19—C24118.39 (10)C19—C18—H18B108.2
C20—C19—C18118.70 (10)H18A—C18—H18B107.4
C24—C19—C18122.85 (10)C21—C20—H20A119.5
C21—C20—C19121.04 (11)C19—C20—H20A119.5
C22—C21—C20120.00 (12)C22—C21—H21A120.0
C21—C22—C23119.75 (11)C20—C21—H21A120.0
C22—C23—C24120.25 (11)C21—C22—H22A120.1
C23—C24—C19120.53 (11)C23—C22—H22A120.1
C1—C4—H4A108.4C22—C23—H23A119.9
C5—C4—H4A108.4C24—C23—H23A119.9
C1—C4—H4B108.4C23—C24—H24A119.7
C5—C4—H4B108.4C19—C24—H24A119.7
H4A—C4—H4B107.4
C3i—C1—C2—C31.47 (16)C2—C11—C12—C1727.20 (15)
C4—C1—C2—C3177.89 (9)C2—C11—C12—C13155.64 (10)
C3i—C1—C2—C11178.49 (9)C17—C12—C13—C140.78 (17)
C4—C1—C2—C112.15 (14)C11—C12—C13—C14176.52 (11)
C1—C2—C3—C1i1.47 (16)C12—C13—C14—C150.00 (19)
C11—C2—C3—C1i178.49 (9)C13—C14—C15—C160.3 (2)
C1—C2—C3—C18177.57 (9)C14—C15—C16—C170.2 (2)
C11—C2—C3—C182.47 (14)C15—C16—C17—C121.0 (2)
C3i—C1—C4—C584.10 (12)C13—C12—C17—C161.25 (18)
C2—C1—C4—C596.54 (12)C11—C12—C17—C16175.95 (11)
C1—C4—C5—C632.98 (15)C1i—C3—C18—C1991.99 (12)
C1—C4—C5—C10149.86 (11)C2—C3—C18—C1988.97 (12)
C10—C5—C6—C71.95 (17)C3—C18—C19—C20158.64 (10)
C4—C5—C6—C7175.26 (11)C3—C18—C19—C2424.43 (15)
C5—C6—C7—C80.89 (19)C24—C19—C20—C212.08 (18)
C6—C7—C8—C90.8 (2)C18—C19—C20—C21174.99 (11)
C7—C8—C9—C101.3 (2)C19—C20—C21—C220.6 (2)
C8—C9—C10—C50.3 (2)C20—C21—C22—C231.0 (2)
C6—C5—C10—C91.38 (19)C21—C22—C23—C241.05 (19)
C4—C5—C10—C9175.89 (12)C22—C23—C24—C190.48 (18)
C3—C2—C11—C1293.95 (12)C20—C19—C24—C232.02 (17)
C1—C2—C11—C1286.09 (12)C18—C19—C24—C23174.92 (10)
Symmetry code: (i) x, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC48H42
Mr618.82
Crystal system, space groupTriclinic, P1
Temperature (K)123
a, b, c (Å)8.999 (2), 10.456 (4), 10.622 (4)
α, β, γ (°)69.218 (12), 79.20 (2), 67.07 (2)
V3)859.2 (5)
Z1
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.45 × 0.35 × 0.30
Data collection
DiffractometerBruker 1K CCD
diffractometer
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.970, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
8524, 3460, 3077
Rint0.016
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.111, 1.01
No. of reflections3460
No. of parameters238
H-atom treatmentConstrained (see text)
Δρmax, Δρmin (e Å3)0.23, 0.25

Computer programs: SMART (Bruker, 1999), SMART and SAINT (Bruker, 1999), SAINT (Bruker, 1999), SHELXTL (Sheldrick, 1999).

 

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