Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199016005/qa0192sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270199016005/qa0192Isup2.hkl |
CCDC reference: 140863
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).
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.
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).
C48H42 | F(000) = 330 |
Mr = 618.82 | Dx = 1.196 Mg m−3 |
Triclinic, P1 | Melting point: 581 K |
a = 8.999 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.456 (4) Å | Cell parameters from 7886 reflections |
c = 10.622 (4) Å | θ = 2.1–29.0° |
α = 69.218 (12)° | µ = 0.07 mm−1 |
β = 79.20 (2)° | T = 123 K |
γ = 67.07 (2)° | Prism, colourless |
V = 859.2 (5) Å3 | 0.45 × 0.35 × 0.30 mm |
Z = 1 |
Bruker 1K CCD diffractometer | 3460 independent reflections |
Radiation source: fine-focus sealed tube | 3077 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.4°, θmin = 2.1° |
ω rotation with narrow frames scans | h = −11→11 |
Absorption correction: multi-scan (Blessing, 1995) | k = −13→13 |
Tmin = 0.970, Tmax = 1.000 | l = −13→13 |
8524 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | Constrained (see text) |
S = 1.01 | Calculated w = 1/[σ2(Fo2) + (0.065P)2 + 0.25P] where P = (Fo2 + 2Fc2)/3 |
3460 reflections | (Δ/σ)max = 0.001 |
238 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C48H42 | γ = 67.07 (2)° |
Mr = 618.82 | V = 859.2 (5) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.999 (2) Å | Mo Kα radiation |
b = 10.456 (4) Å | µ = 0.07 mm−1 |
c = 10.622 (4) Å | T = 123 K |
α = 69.218 (12)° | 0.45 × 0.35 × 0.30 mm |
β = 79.20 (2)° |
Bruker 1K CCD diffractometer | 3460 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 3077 reflections with I > 2σ(I) |
Tmin = 0.970, Tmax = 1.000 | Rint = 0.016 |
8524 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.111 | Constrained (see text) |
S = 1.01 | Δρmax = 0.23 e Å−3 |
3460 reflections | Δρmin = −0.25 e Å−3 |
238 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | −0.10337 (13) | 0.60890 (11) | 0.90052 (11) | 0.0175 (2) | |
C2 | 0.06401 (13) | 0.57960 (11) | 0.88087 (11) | 0.0175 (2) | |
C3 | 0.16692 (12) | 0.47171 (11) | 0.98130 (11) | 0.0172 (2) | |
C4 | −0.21690 (13) | 0.72886 (12) | 0.79495 (11) | 0.0205 (2) | |
H4A | −0.1647 | 0.8013 | 0.7434 | 0.021 (3)* | |
H4B | −0.3163 | 0.7794 | 0.8420 | 0.026 (3)* | |
C5 | −0.26535 (14) | 0.67912 (12) | 0.69550 (11) | 0.0214 (2) | |
C6 | −0.16092 (14) | 0.56147 (13) | 0.65280 (12) | 0.0238 (3) | |
H6A | −0.0591 | 0.5053 | 0.6912 | 0.024 (3)* | |
C7 | −0.20429 (16) | 0.52524 (15) | 0.55426 (13) | 0.0306 (3) | |
H7A | −0.1312 | 0.4455 | 0.5252 | 0.038 (4)* | |
C8 | −0.35279 (17) | 0.60437 (18) | 0.49853 (13) | 0.0377 (3) | |
H8A | −0.3816 | 0.5803 | 0.4306 | 0.050 (5)* | |
C9 | −0.45902 (17) | 0.71912 (19) | 0.54286 (14) | 0.0417 (4) | |
H9A | −0.5623 | 0.7727 | 0.5064 | 0.051 (5)* | |
C10 | −0.41604 (15) | 0.75661 (15) | 0.64015 (13) | 0.0320 (3) | |
H10A | −0.4901 | 0.8359 | 0.6694 | 0.044 (4)* | |
C11 | 0.13380 (14) | 0.66425 (12) | 0.75129 (11) | 0.0209 (2) | |
H11A | 0.0700 | 0.6835 | 0.6759 | 0.025 (3)* | |
H11B | 0.2457 | 0.6016 | 0.7338 | 0.026 (3)* | |
C12 | 0.13691 (13) | 0.80916 (12) | 0.75059 (11) | 0.0206 (2) | |
C13 | 0.13827 (14) | 0.91764 (13) | 0.62769 (12) | 0.0264 (3) | |
H13A | 0.1312 | 0.9019 | 0.5466 | 0.035 (4)* | |
C14 | 0.14983 (16) | 1.04827 (14) | 0.62182 (14) | 0.0329 (3) | |
H14A | 0.1506 | 1.1209 | 0.5371 | 0.039 (4)* | |
C15 | 0.16028 (16) | 1.07299 (14) | 0.73909 (15) | 0.0339 (3) | |
H15A | 0.1687 | 1.1621 | 0.7352 | 0.043 (4)* | |
C16 | 0.15829 (17) | 0.96680 (14) | 0.86206 (14) | 0.0332 (3) | |
H16A | 0.1657 | 0.9831 | 0.9428 | 0.044 (4)* | |
C17 | 0.14549 (15) | 0.83617 (13) | 0.86801 (12) | 0.0267 (3) | |
H17A | 0.1426 | 0.7647 | 0.9531 | 0.032 (4)* | |
C18 | 0.34726 (13) | 0.44372 (12) | 0.96305 (11) | 0.0193 (2) | |
H18A | 0.3893 | 0.4109 | 1.0532 | 0.021 (3)* | |
H18B | 0.3629 | 0.5376 | 0.9118 | 0.025 (3)* | |
C19 | 0.44896 (13) | 0.33194 (12) | 0.89139 (11) | 0.0187 (2) | |
C20 | 0.59931 (14) | 0.33613 (13) | 0.83171 (13) | 0.0260 (3) | |
H20A | 0.6320 | 0.4128 | 0.8303 | 0.035 (4)* | |
C21 | 0.70214 (15) | 0.23011 (14) | 0.77424 (14) | 0.0316 (3) | |
H21A | 0.8047 | 0.2340 | 0.7347 | 0.041 (4)* | |
C22 | 0.65524 (16) | 0.11880 (13) | 0.77457 (13) | 0.0298 (3) | |
H22A | 0.7261 | 0.0453 | 0.7366 | 0.041 (4)* | |
C23 | 0.50464 (16) | 0.11490 (13) | 0.83048 (13) | 0.0279 (3) | |
H23A | 0.4715 | 0.0394 | 0.8295 | 0.037 (4)* | |
C24 | 0.40151 (14) | 0.22119 (13) | 0.88824 (12) | 0.0235 (3) | |
H24A | 0.2980 | 0.2182 | 0.9258 | 0.029 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0189 (5) | 0.0171 (5) | 0.0188 (5) | −0.0064 (4) | −0.0010 (4) | −0.0083 (4) |
C2 | 0.0195 (5) | 0.0180 (5) | 0.0181 (5) | −0.0083 (4) | 0.0008 (4) | −0.0081 (4) |
C3 | 0.0165 (5) | 0.0187 (5) | 0.0202 (5) | −0.0073 (4) | 0.0009 (4) | −0.0102 (4) |
C4 | 0.0194 (5) | 0.0193 (5) | 0.0211 (5) | −0.0051 (4) | −0.0018 (4) | −0.0059 (4) |
C5 | 0.0206 (5) | 0.0265 (6) | 0.0161 (5) | −0.0101 (4) | 0.0001 (4) | −0.0041 (4) |
C6 | 0.0204 (6) | 0.0295 (6) | 0.0233 (6) | −0.0110 (5) | 0.0012 (4) | −0.0091 (5) |
C7 | 0.0310 (6) | 0.0422 (7) | 0.0268 (6) | −0.0192 (6) | 0.0072 (5) | −0.0175 (5) |
C8 | 0.0349 (7) | 0.0655 (10) | 0.0241 (6) | −0.0246 (7) | 0.0009 (5) | −0.0206 (6) |
C9 | 0.0270 (7) | 0.0669 (10) | 0.0299 (7) | −0.0093 (7) | −0.0084 (5) | −0.0180 (7) |
C10 | 0.0240 (6) | 0.0406 (7) | 0.0260 (6) | −0.0034 (5) | −0.0044 (5) | −0.0117 (5) |
C11 | 0.0213 (5) | 0.0242 (5) | 0.0188 (5) | −0.0106 (4) | 0.0017 (4) | −0.0071 (4) |
C12 | 0.0151 (5) | 0.0218 (5) | 0.0236 (6) | −0.0077 (4) | −0.0001 (4) | −0.0047 (4) |
C13 | 0.0218 (6) | 0.0288 (6) | 0.0249 (6) | −0.0101 (5) | −0.0040 (4) | −0.0012 (5) |
C14 | 0.0277 (6) | 0.0259 (6) | 0.0370 (7) | −0.0130 (5) | −0.0059 (5) | 0.0054 (5) |
C15 | 0.0288 (7) | 0.0230 (6) | 0.0510 (8) | −0.0131 (5) | −0.0046 (6) | −0.0073 (6) |
C16 | 0.0367 (7) | 0.0309 (7) | 0.0379 (7) | −0.0159 (6) | −0.0011 (6) | −0.0137 (6) |
C17 | 0.0315 (6) | 0.0253 (6) | 0.0251 (6) | −0.0140 (5) | 0.0014 (5) | −0.0067 (5) |
C18 | 0.0167 (5) | 0.0221 (5) | 0.0215 (5) | −0.0079 (4) | −0.0002 (4) | −0.0088 (4) |
C19 | 0.0174 (5) | 0.0206 (5) | 0.0164 (5) | −0.0052 (4) | −0.0020 (4) | −0.0049 (4) |
C20 | 0.0212 (6) | 0.0272 (6) | 0.0310 (6) | −0.0095 (5) | 0.0023 (5) | −0.0116 (5) |
C21 | 0.0217 (6) | 0.0330 (7) | 0.0365 (7) | −0.0070 (5) | 0.0065 (5) | −0.0137 (5) |
C22 | 0.0309 (7) | 0.0231 (6) | 0.0283 (6) | −0.0013 (5) | 0.0025 (5) | −0.0111 (5) |
C23 | 0.0344 (7) | 0.0229 (6) | 0.0278 (6) | −0.0098 (5) | −0.0009 (5) | −0.0100 (5) |
C24 | 0.0227 (6) | 0.0261 (6) | 0.0235 (6) | −0.0099 (5) | 0.0008 (4) | −0.0093 (5) |
C1—C3i | 1.4032 (16) | C21—C22 | 1.3828 (19) |
C1—C2 | 1.4051 (15) | C22—C23 | 1.3839 (19) |
C1—C4 | 1.5190 (16) | C23—C24 | 1.3927 (17) |
C2—C3 | 1.4036 (16) | C4—H4A | 0.9900 |
C2—C11 | 1.5221 (15) | C4—H4B | 0.9900 |
C3—C1i | 1.4032 (16) | C6—H6A | 0.9500 |
C3—C18 | 1.5196 (14) | C7—H7A | 0.9500 |
C4—C5 | 1.5217 (16) | C8—H8A | 0.9500 |
C5—C6 | 1.3919 (17) | C9—H9A | 0.9500 |
C5—C10 | 1.3949 (17) | C10—H10A | 0.9500 |
C6—C7 | 1.3932 (17) | C11—H11A | 0.9900 |
C7—C8 | 1.381 (2) | C11—H11B | 0.9900 |
C8—C9 | 1.383 (2) | C13—H13A | 0.9500 |
C9—C10 | 1.3880 (19) | C14—H14A | 0.9500 |
C11—C12 | 1.5237 (16) | C15—H15A | 0.9500 |
C12—C17 | 1.3944 (17) | C16—H16A | 0.9500 |
C12—C13 | 1.3946 (17) | C17—H17A | 0.9500 |
C13—C14 | 1.3886 (18) | C18—H18A | 0.9900 |
C14—C15 | 1.385 (2) | C18—H18B | 0.9900 |
C15—C16 | 1.384 (2) | C20—H20A | 0.9500 |
C16—C17 | 1.3934 (18) | C21—H21A | 0.9500 |
C18—C19 | 1.5230 (15) | C22—H22A | 0.9500 |
C19—C20 | 1.3926 (16) | C23—H23A | 0.9500 |
C19—C24 | 1.3938 (16) | C24—H24A | 0.9500 |
C20—C21 | 1.3882 (17) | ||
C3i—C1—C2 | 120.10 (10) | C5—C6—H6A | 119.7 |
C3i—C1—C4 | 119.54 (10) | C7—C6—H6A | 119.7 |
C2—C1—C4 | 120.36 (10) | C8—C7—H7A | 119.8 |
C3—C2—C1 | 119.72 (10) | C6—C7—H7A | 119.8 |
C3—C2—C11 | 120.03 (10) | C7—C8—H8A | 120.4 |
C1—C2—C11 | 120.25 (10) | C9—C8—H8A | 120.4 |
C1i—C3—C2 | 120.16 (10) | C8—C9—H9A | 119.7 |
C1i—C3—C18 | 119.88 (10) | C10—C9—H9A | 119.7 |
C2—C3—C18 | 119.95 (10) | C9—C10—H10A | 119.6 |
C1—C4—C5 | 115.69 (9) | C5—C10—H10A | 119.6 |
C6—C5—C10 | 118.28 (11) | C2—C11—H11A | 108.4 |
C6—C5—C4 | 122.04 (10) | C12—C11—H11A | 108.4 |
C10—C5—C4 | 119.62 (11) | C2—C11—H11B | 108.4 |
C5—C6—C7 | 120.67 (11) | C12—C11—H11B | 108.4 |
C8—C7—C6 | 120.50 (12) | H11A—C11—H11B | 107.5 |
C7—C8—C9 | 119.23 (12) | C14—C13—H13A | 119.4 |
C8—C9—C10 | 120.57 (13) | C12—C13—H13A | 119.4 |
C9—C10—C5 | 120.73 (12) | C15—C14—H14A | 119.9 |
C2—C11—C12 | 115.52 (9) | C13—C14—H14A | 119.9 |
C17—C12—C13 | 118.11 (11) | C16—C15—H15A | 120.3 |
C17—C12—C11 | 122.63 (10) | C14—C15—H15A | 120.3 |
C13—C12—C11 | 119.20 (11) | C15—C16—H16A | 119.8 |
C14—C13—C12 | 121.13 (12) | C17—C16—H16A | 119.8 |
C15—C14—C13 | 120.18 (12) | C16—C17—H17A | 119.6 |
C16—C15—C14 | 119.48 (12) | C12—C17—H17A | 119.6 |
C15—C16—C17 | 120.34 (12) | C3—C18—H18A | 108.2 |
C16—C17—C12 | 120.76 (11) | C19—C18—H18A | 108.2 |
C3—C18—C19 | 116.33 (9) | C3—C18—H18B | 108.2 |
C20—C19—C24 | 118.39 (10) | C19—C18—H18B | 108.2 |
C20—C19—C18 | 118.70 (10) | H18A—C18—H18B | 107.4 |
C24—C19—C18 | 122.85 (10) | C21—C20—H20A | 119.5 |
C21—C20—C19 | 121.04 (11) | C19—C20—H20A | 119.5 |
C22—C21—C20 | 120.00 (12) | C22—C21—H21A | 120.0 |
C21—C22—C23 | 119.75 (11) | C20—C21—H21A | 120.0 |
C22—C23—C24 | 120.25 (11) | C21—C22—H22A | 120.1 |
C23—C24—C19 | 120.53 (11) | C23—C22—H22A | 120.1 |
C1—C4—H4A | 108.4 | C22—C23—H23A | 119.9 |
C5—C4—H4A | 108.4 | C24—C23—H23A | 119.9 |
C1—C4—H4B | 108.4 | C23—C24—H24A | 119.7 |
C5—C4—H4B | 108.4 | C19—C24—H24A | 119.7 |
H4A—C4—H4B | 107.4 | ||
C3i—C1—C2—C3 | −1.47 (16) | C2—C11—C12—C17 | 27.20 (15) |
C4—C1—C2—C3 | 177.89 (9) | C2—C11—C12—C13 | −155.64 (10) |
C3i—C1—C2—C11 | 178.49 (9) | C17—C12—C13—C14 | 0.78 (17) |
C4—C1—C2—C11 | −2.15 (14) | C11—C12—C13—C14 | −176.52 (11) |
C1—C2—C3—C1i | 1.47 (16) | C12—C13—C14—C15 | 0.00 (19) |
C11—C2—C3—C1i | −178.49 (9) | C13—C14—C15—C16 | −0.3 (2) |
C1—C2—C3—C18 | −177.57 (9) | C14—C15—C16—C17 | −0.2 (2) |
C11—C2—C3—C18 | 2.47 (14) | C15—C16—C17—C12 | 1.0 (2) |
C3i—C1—C4—C5 | −84.10 (12) | C13—C12—C17—C16 | −1.25 (18) |
C2—C1—C4—C5 | 96.54 (12) | C11—C12—C17—C16 | 175.95 (11) |
C1—C4—C5—C6 | −32.98 (15) | C1i—C3—C18—C19 | 91.99 (12) |
C1—C4—C5—C10 | 149.86 (11) | C2—C3—C18—C19 | −88.97 (12) |
C10—C5—C6—C7 | 1.95 (17) | C3—C18—C19—C20 | 158.64 (10) |
C4—C5—C6—C7 | −175.26 (11) | C3—C18—C19—C24 | −24.43 (15) |
C5—C6—C7—C8 | −0.89 (19) | C24—C19—C20—C21 | −2.08 (18) |
C6—C7—C8—C9 | −0.8 (2) | C18—C19—C20—C21 | 174.99 (11) |
C7—C8—C9—C10 | 1.3 (2) | C19—C20—C21—C22 | 0.6 (2) |
C8—C9—C10—C5 | −0.3 (2) | C20—C21—C22—C23 | 1.0 (2) |
C6—C5—C10—C9 | −1.38 (19) | C21—C22—C23—C24 | −1.05 (19) |
C4—C5—C10—C9 | 175.89 (12) | C22—C23—C24—C19 | −0.48 (18) |
C3—C2—C11—C12 | −93.95 (12) | C20—C19—C24—C23 | 2.02 (17) |
C1—C2—C11—C12 | 86.09 (12) | C18—C19—C24—C23 | −174.92 (10) |
Symmetry code: (i) −x, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C48H42 |
Mr | 618.82 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 859.2 (5) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.45 × 0.35 × 0.30 |
Data collection | |
Diffractometer | Bruker 1K CCD diffractometer |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.970, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8524, 3460, 3077 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.111, 1.01 |
No. of reflections | 3460 |
No. of parameters | 238 |
H-atom treatment | Constrained (see text) |
Δρmax, Δρmin (e Å−3) | 0.23, −0.25 |
Computer programs: SMART (Bruker, 1999), SMART and SAINT (Bruker, 1999), SAINT (Bruker, 1999), SHELXTL (Sheldrick, 1999).
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