1. Chemical context
Pentafulvenes have garnered interested because of their unique cross-conjugated electronic system. Fulvenes have been explored for applications as chromophores (Jayamurugan et al., 2013), frustrated Lewis pair scaffolds (Mömming et al., 2011), and ligands for metal–fulvene complexes (Erker, 2011). To facilitate the inclusion in transition-metal complexes, reduction to a cyclopentadiene ligand (Gómez-Ruiz et al., 2005) or reductive coupling to ansa bis-cyclopentadiene ligand (Adas & Balaich, 2018) are the most common reactions. As part of our work in this area, we now report the syntheses and crystal structures of a series of 1,3-diphenylfulvenes bearing 6-phenyl substituent with diverse methylation patterns, viz. 1,3-diphenyl-6-(3-methylphenyl)fulvene (C25H20) I, 1,3-diphenyl-6-(4-methylphenyl)fulvene (C25H20) II, 3-diphenyl-6-mesitylfulvene (C27H24) III and 1,3-diphenyl-6-(2,3,4,5,6-pentamethylphenyl)fulvene (C29H28) IV (Figs. 1–4).
| Figure 1 The molecular structure of I. Displacement ellipsoids are shown at the 50% probability level. |
| Figure 2 The molecular structure of II. Displacement ellipsoids are shown at the 50% probability level. |
| Figure 3 The molecular structure of III. Displacement ellipsoids are shown at the 50% probability level. |
| Figure 4 The molecular structure of IV. Displacement ellipsoids are shown at the 50% probability level. |
2. Structural commentary
Compounds I and IV crystallize in the monoclinic space group C2/c (Fig. 1), compound II in the monoclinic space group P21/c, and compound III the orthorhombic space group Pca21. With the exception of III, in which the asymmetric unit contains two complete fulvene molecules, each compound crystallizes with one molecule per asymmetric unit. In each compound, the expected alternating long–short intra-ring bond lengths are observed. The phenyl substituents are rotated from 19.50 (6) to 64.15 (7)° from the cyclopentadiene core of the fulvene (Table 1). The rotation is larger for each substituent in IV, likely because of the additional steric interactions provided by the pentamethyl substituent.
| I | II | III | IV | Fulvenea-(1-phenylb) | 32.08 (7) | 31.83 (5) | 21.33 (13) | 41.65 (7) | Fulvenea-(3-phenylb) | 19.50 (6) | 20.92 (5) | 38.02 (13) | 25.17 (7) | Fulvenea-(6-phenylb) | 31.99 (6) | 35.13 (5) | 57.22 (14) | 64.15 (7) | Notes: (a) plane defined by atoms C1–C5; (a) plane defined by the atoms of the specific phenyl ring substituent. | |
For fulvene I, the phenyl substituents are rotated 32.08 (7), 19.50 (6) and 31.99 (6)° from the cyclopentadiene core for the 1-phenyl, 3-phenyl, and 6-phenyl substituents, respectively. In compound II, the phenyl substituents are rotated 31.83 (5), 20.92 (5) and 35.13 (5)° from the cyclopentadiene core for the 1-phenyl, 3-phenyl, and 6-phenyl substituents, respectively. For compound III, the phenyl substituents are rotated an average of 21.33 (13), 38.02 (13) and 57.22 (14)° from the cyclopentadiene core for the 1-phenyl, 3-phenyl, and 6-phenyl substituents, respectively. In fulvene IV, each phenyl ring is rotated further from the core of the fulvene molecule, likely because of the additional steric interactions provided by the pentamethylphenyl substituent. The phenyl substituents are rotated by 41.65 (7), 25.17 (7) and 64.15 (7)° from the cyclopentadiene core for the 1-phenyl, 3-phenyl, and 6-phenyl substituents, respectively.
3. Supramolecular features
The packing for each compound I–IV is consolidated through a series of C—H⋯π ring interactions. In I, each molecule participates in C—H⋯π ring interactions with six other fulvene molecules. Each molecule acts as a C—H donor through the hydrogen atoms in the para position of each phenyl substituent, H10 and H16, as well as a meta hydrogen atom, H23, from the 6-(3-methylphenyl) substituent. Additionally, the π ring of the 3-phenyl and 6-(3-methylphenyl) substituents accept C—H interactions, with the latter accepting donations from both sides of the ring (Table 2 and Fig. 5). In the crystal structure of II, each molecule interacts with five other fulvene molecules. Phenyl hydrogen atoms H12 and H17 as well as methyl hydrogen atom H25A act as donors. The 3-phenyl and 6-(4-methylphenyl) substituents act as C—H acceptors, with the former accepting donations from both sides of the ring (Table 3 and Fig. 6). The interactions differ between the two molecules within the asymmetric unit of III. One of the molecules contributes four C—H donor sites, H37, H39, H53A, and H54C, with the π ring of each phenyl substituent as well as the fulvene core acting as acceptors. In the other molecule, H10 and H25C act as C—H donors with the π system of the 1-phenyl and 3-phenyl substituents accepting, the latter accepting C—H interactions from both sides of the ring (Table 4 and Fig. 7). Fulvene IV interacts with four other molecules via C—H⋯π ring interactions. The para hydrogen atom of the 1-phenyl substituent and one of the hydrogen atoms of the para methyl group of the 6-(2,3,4,5,6-pentametyhlphenyl) substituent, H27C, serve as C—H donors for two separate fulvene molecules. The 6-(2,3,4,5,6-pentametyhlphenyl) π ring accepts C—H donation from two additional molecules (Table 5 and Fig. 8).
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | C10—H10⋯Cg1i | 0.93 | 2.83 | 3.539 (2) | 134 | C16—H16⋯Cg2ii | 0.93 | 2.86 | 3.589 (2) | 136 | C23—H23⋯Cg2iii | 0.93 | 2.90 | 3.547 (2) | 128 | Symmetry codes: (i) ; (ii) ; (iii) . | |
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | C12—H12⋯Cg3i | 0.95 | 2.95 | 3.6560 (4) | 132 | C17—H17⋯Cg3ii | 0.95 | 2.83 | 3.4837 (4) | 127 | C25—H25A⋯Cg4iii | 0.98 | 2.98 | 3.8277 (4) | 145 | Symmetry codes: (i) ; (ii) ; (iii) -x+1, -y+1, -z+1. | |
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | C10—H10⋯Cg5i | 0.93 | 2.81 | 3.5059 (7) | 132 | C25—H25C⋯Cg6ii | 0.96 | 2.81 | 3.7115 (8) | 158 | C37—H37⋯Cg7iii | 0.93 | 2.71 | 3.5129 (8) | 145 | C39—H39⋯Cg8ii | 0.93 | 2.97 | 3.5817 (8) | 125 | C53—H53A⋯Cg7iv | 0.96 | 2.94 | 3.6503 (8) | 132 | C54—H54C⋯Cg9v | 0.96 | 2.88 | 3.7983 (8) | 160 | Symmetry codes: (i) ; (ii) x, y+1, z; (iii) ; (iv) ; (v) x, y-1, z. | |
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | C10—H10⋯Cg10i | 0.95 | 2.70 | 3.4521 (9) | 136 | Symmetry code: (i) . | |
| Figure 5 The crystal packing of I. Displacement ellipsoids are shown at the 50% probability level. C—H⋯π ring interactions (Table 2) are shown as dashed lines. |
| Figure 6 The crystal packing of II. Displacement ellipsoids are shown at the 50% probability level. C—H⋯π ring interactions (Table 3) are shown as dashed lines. |
| Figure 7 The crystal packing of III. Displacement ellipsoids are shown at the 50% probability level. C—H⋯π ring interactions (Table 4) are shown as dashed lines. |
| Figure 8 The crystal packing of IV, viewed along the b axis. Displacement ellipsoids are shown at the 50% probability level. C—H⋯π ring interactions (Table 5) are shown as dashed lines. |
4. Database survey
A survey of the November 2019 release of the Cambridge Structure Database (Groom et al., 2016), with updates through February 2019, was made using the program Mogul (Bruno et al., 2004). A search for 1,3-diphenyl fulvenes and 6-aryl-1,3-diphenyl fulvenes yielded 78 and 35 results, respectively. In both cases, the phenyl–fulvene torsion angles produce a bimodal distribution with broad peaks at 50 and 130°. The torsion angles in I–IV are therefore not unusual.
5. Synthesis and crystallization
Each compound was prepared by a modified literature procedure (Peloquin et al., 2012).
1,3-diphenyl-6-(3-methylphenyl)fulvene (I). To a vigorously stirred solution of 1,3-diphenylcyclopentadiene (0.230 g, 1.05 mmol) in absolute EtOH (25 ml), 3-methylbenzaldehyde (0.189 g, 1.58 mmol) and pyrrolidine (0.12 g, 1.68 mmol) were added. The reaction mixture was allowed to stir at room temperature for 22 h. The precipitate from the reaction mixture was vacuum filtered, washed with cold absolute EtOH (3 × 30 ml), and vacuum dried to give I as a dark-red solid (0.211 g, 63%). Red prisms suitable for single-crystal X-ray diffraction were obtained from diethyl ether solution by slow evaporation.
1,3-diphenyl-6-(4-methylphenyl)fulvene (II). To a vigorously stirred solution of 1,3-diphenylcyclopentadiene (0.336 g, 1.42 mmol) in absolute EtOH (8 ml), 4-methylbenzaldehyde (0.25 ml, 2.13 mmol) and pyrrolidine (0.14 ml, 1.70 mmol) were added. The reaction mixture was allowed to stir at room temperature for 24 h. The precipitate from the reaction mixture was vacuum filtered, washed with cold absolute EtOH (3 × 30 ml), and vacuum dried to give II as a dark-red solid (0.251 g, 75%). Red prisms suitable for single-crystal X-ray diffraction were obtained from diethyl ether solution by slow evaporation.
3-diphenyl-6-mesitylfulvene (III). To a vigorously stirred solution of 1,3-diphenylcyclopentadiene (1.434 g, 6.57 mmol) in absolute EtOH (50 ml), mesitylaldehyde (1.173 g, 7.91 mmol) and pyrrolidine (0.789 g, 11.09 mmol) were added. The reaction mixture was allowed to stir at reflux for 24 h. The reaction mixture was cooled to 278 K and the resulting precipitate was vacuum filtered, washed with cold absolute EtOH (3 × 30 ml), and vacuum dried to give III as a red–orange solid (1.85 g, 81%). Irregular red crystals suitable for single-crystal X-ray diffraction were obtained from pentane solution by slow evaporation.
1,3-diphenyl-6-(2,3,4,5,6-pentamethylphenyl)fulvene (IV). To a vigorously stirred solution of 1,3-diphenylcyclopentadiene (2.1 g, 9.62 mmol) in absolute EtOH (50 ml), 2,3,4,5,6-pentamethylbenzaldehyde (2.04 g, 11.55 mmol) and pyrrolidine (1.09 g, 15.40 mmol) were added. The reaction mixture was allowed to stir at room temperature for 24 h. The precipitate from the reaction mixture was vacuum filtered, washed with cold absolute EtOH (3 × 30 ml), and vacuum dried to give IV as an orange solid (2.93 g, 82%). Orange needles suitable for single-crystal X-ray diffraction were obtained from ethyl acetate solution by slow evaporation.
6. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 6. H atoms were positioned geometrically and refined as riding with C—H = 0.93–0.96 Å and Uiso(H) = 1.2–1.5Ueq(C). The absolute structure of III was indeterminate in the present refinement. Compound III was refined as an inversion twin.
| (I) | (II) | (III) | (IV) | Crystal data | Chemical formula | C25H20 | C25H20 | C27H24 | C29H28 | Mr | 320.41 | 320.41 | 348.46 | 376.51 | Crystal system, space group | Monoclinic, C2/c | Monoclinic, P21/c | Orthorhombic, Pca21 | Monoclinic, C2/c | Temperature (K) | 100 | 100 | 100 | 100 | a, b, c (Å) | 29.230 (17), 5.800 (3), 22.071 (12) | 19.208 (2), 5.8774 (7), 16.1884 (18) | 30.031 (6), 5.6147 (12), 23.494 (5) | 30.987 (7), 5.8273 (14), 23.557 (6) | α, β, γ (°) | 90, 107.248 (17), 90 | 90, 107.710 (1), 90 | 90, 90, 90 | 90, 96.192 (3), 90 | V (Å3) | 3573 (3) | 1740.9 (3) | 3961.4 (14) | 4228.9 (17) | Z | 8 | 4 | 8 | 8 | Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα | μ (mm−1) | 0.07 | 0.07 | 0.07 | 0.07 | Crystal size (mm) | 0.25 × 0.21 × 0.18 | 0.43 × 0.27 × 0.06 | 0.26 × 0.11 × 0.10 | 0.44 × 0.11 × 0.1 | | Data collection | Diffractometer | Bruker APEXII CCD | Bruker APEXII CCD | Bruker APEXII CCD | Bruker APEXII CCD | Absorption correction | Multi-scan SADABS | Multi-scan SADABS | Multi-scan SADABS | Multi-scan SADABS | Tmin, Tmax | 0.832, 0.901 | 0.691, 0.745 | 0.678, 0.745 | 0.587, 0.745 | No. of measured, independent and observed [I > 2σ(I)] reflections | 31841, 3817, 3013 | 30237, 3473, 2972 | 38475, 6776, 5709 | 37965, 4394, 3213 | Rint | 0.052 | 0.038 | 0.070 | 0.082 | (sin θ/λ)max (Å−1) | 0.635 | 0.620 | 0.590 | 0.629 | | Refinement | R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.122, 1.05 | 0.040, 0.100, 1.04 | 0.043, 0.108, 1.04 | 0.050, 0.137, 1.03 | No. of reflections | 3817 | 3473 | 6776 | 4394 | No. of parameters | 227 | 227 | 494 | 267 | No. of restraints | 0 | 0 | 1 | 0 | H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | Δρmax, Δρmin (e Å−3) | 0.33, −0.20 | 0.22, −0.19 | 0.17, −0.17 | 0.24, −0.22 | Absolute structure | – | – | Refined as an inversion twin. | – | Absolute structure parameter | – | – | −6 (10) | – | Computer programs: APEX3 and SAINT (Bruker, 2017), SHELXT (Sheldrick, 2015a), SHELXL (Sheldrick, 2015b), ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae, et al., 2008) and publCIF (Westrip, 2010). | |
Supporting information
For all structures, data collection: APEX3 (Bruker, 2017); cell refinement: SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae, et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
{3-[(3-Methylphenyl)methylidene]-4-phenylcyclopenta-1,4-dien-1-yl}benzene (I)
top Crystal data top C25H20 | F(000) = 1360 |
Mr = 320.41 | Dx = 1.191 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 29.230 (17) Å | Cell parameters from 4339 reflections |
b = 5.800 (3) Å | θ = 2.9–24.4° |
c = 22.071 (12) Å | µ = 0.07 mm−1 |
β = 107.248 (17)° | T = 100 K |
V = 3573 (3) Å3 | Prism, red |
Z = 8 | 0.25 × 0.21 × 0.18 mm |
Data collection top Bruker APEXII CCD diffractometer | 3013 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.052 |
Absorption correction: multi-scan SADABS | θmax = 26.8°, θmin = 1.9° |
Tmin = 0.832, Tmax = 0.901 | h = −36→36 |
31841 measured reflections | k = −7→7 |
3817 independent reflections | l = −28→27 |
Refinement top Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0482P)2 + 3.8961P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3817 reflections | Δρmax = 0.33 e Å−3 |
227 parameters | Δρmin = −0.19 e Å−3 |
Special details top Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.57871 (5) | 0.4490 (3) | 0.23560 (7) | 0.0219 (3) | |
C2 | 0.57462 (5) | 0.4576 (3) | 0.29513 (7) | 0.0229 (3) | |
H2 | 0.554463 | 0.364773 | 0.310252 | 0.027* | |
C3 | 0.60677 (5) | 0.6356 (3) | 0.33229 (7) | 0.0222 (3) | |
C4 | 0.62991 (5) | 0.7360 (3) | 0.29436 (7) | 0.0235 (3) | |
H4 | 0.651702 | 0.856706 | 0.305993 | 0.028* | |
C5 | 0.61519 (5) | 0.6246 (3) | 0.23236 (7) | 0.0221 (3) | |
C6 | 0.63418 (5) | 0.6503 (3) | 0.18410 (7) | 0.0238 (3) | |
H6 | 0.623184 | 0.548206 | 0.150415 | 0.029* | |
C7 | 0.55041 (5) | 0.2988 (3) | 0.18388 (7) | 0.0218 (3) | |
C8 | 0.53551 (5) | 0.3688 (3) | 0.12045 (7) | 0.0255 (3) | |
H8 | 0.544591 | 0.512625 | 0.109349 | 0.031* | |
C9 | 0.50730 (6) | 0.2255 (3) | 0.07390 (8) | 0.0303 (4) | |
H9 | 0.498411 | 0.272695 | 0.031741 | 0.036* | |
C10 | 0.49212 (6) | 0.0122 (3) | 0.08943 (8) | 0.0306 (4) | |
H10 | 0.472725 | −0.081758 | 0.058066 | 0.037* | |
C11 | 0.50628 (6) | −0.0585 (3) | 0.15223 (8) | 0.0275 (4) | |
H11 | 0.496034 | −0.199944 | 0.163231 | 0.033* | |
C12 | 0.53569 (5) | 0.0812 (3) | 0.19877 (7) | 0.0235 (3) | |
H12 | 0.545815 | 0.029678 | 0.240537 | 0.028* | |
C13 | 0.61345 (5) | 0.6870 (3) | 0.39949 (7) | 0.0235 (3) | |
C14 | 0.59996 (6) | 0.5279 (3) | 0.43855 (7) | 0.0269 (4) | |
H14 | 0.586124 | 0.388692 | 0.421668 | 0.032* | |
C15 | 0.60698 (6) | 0.5755 (3) | 0.50228 (8) | 0.0320 (4) | |
H15 | 0.597703 | 0.468403 | 0.527717 | 0.038* | |
C16 | 0.62776 (6) | 0.7819 (3) | 0.52829 (8) | 0.0331 (4) | |
H16 | 0.632614 | 0.813134 | 0.571065 | 0.040* | |
C17 | 0.64122 (6) | 0.9410 (3) | 0.49002 (8) | 0.0334 (4) | |
H17 | 0.655280 | 1.079353 | 0.507240 | 0.040* | |
C18 | 0.63390 (6) | 0.8956 (3) | 0.42650 (8) | 0.0293 (4) | |
H18 | 0.642674 | 1.004989 | 0.401210 | 0.035* | |
C19 | 0.67002 (5) | 0.8189 (3) | 0.17789 (7) | 0.0233 (3) | |
C20 | 0.69945 (5) | 0.7614 (3) | 0.14047 (7) | 0.0255 (3) | |
H20 | 0.694917 | 0.620567 | 0.119385 | 0.031* | |
C21 | 0.73507 (6) | 0.9072 (3) | 0.13377 (7) | 0.0279 (4) | |
C22 | 0.74101 (6) | 1.1205 (3) | 0.16461 (8) | 0.0302 (4) | |
H22 | 0.764784 | 1.220841 | 0.160703 | 0.036* | |
C23 | 0.71154 (6) | 1.1835 (3) | 0.20115 (7) | 0.0272 (4) | |
H23 | 0.715732 | 1.325711 | 0.221509 | 0.033* | |
C24 | 0.67616 (6) | 1.0360 (3) | 0.20731 (7) | 0.0248 (3) | |
H24 | 0.656224 | 1.080714 | 0.231134 | 0.030* | |
C25 | 0.76705 (7) | 0.8402 (4) | 0.09398 (10) | 0.0443 (5) | |
H25A | 0.759165 | 0.687097 | 0.077736 | 0.066* | |
H25B | 0.799917 | 0.844814 | 0.119636 | 0.066* | |
H25C | 0.762396 | 0.946296 | 0.059275 | 0.066* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0181 (7) | 0.0214 (8) | 0.0268 (8) | 0.0013 (6) | 0.0074 (6) | 0.0003 (6) |
C2 | 0.0207 (7) | 0.0242 (8) | 0.0245 (8) | −0.0022 (6) | 0.0080 (6) | −0.0003 (6) |
C3 | 0.0182 (7) | 0.0229 (8) | 0.0250 (8) | 0.0014 (6) | 0.0055 (6) | 0.0006 (6) |
C4 | 0.0201 (7) | 0.0236 (8) | 0.0252 (8) | 0.0000 (6) | 0.0045 (6) | 0.0001 (6) |
C5 | 0.0197 (7) | 0.0213 (8) | 0.0255 (8) | 0.0025 (6) | 0.0072 (6) | 0.0026 (6) |
C6 | 0.0235 (8) | 0.0237 (8) | 0.0233 (7) | 0.0017 (6) | 0.0055 (6) | −0.0023 (6) |
C7 | 0.0185 (7) | 0.0231 (8) | 0.0255 (8) | 0.0025 (6) | 0.0092 (6) | −0.0032 (6) |
C8 | 0.0252 (8) | 0.0258 (8) | 0.0275 (8) | −0.0001 (7) | 0.0108 (7) | −0.0005 (6) |
C9 | 0.0294 (9) | 0.0375 (10) | 0.0241 (8) | 0.0027 (7) | 0.0083 (7) | −0.0033 (7) |
C10 | 0.0263 (8) | 0.0326 (9) | 0.0322 (9) | −0.0029 (7) | 0.0074 (7) | −0.0127 (7) |
C11 | 0.0256 (8) | 0.0225 (8) | 0.0362 (9) | −0.0012 (7) | 0.0120 (7) | −0.0056 (7) |
C12 | 0.0215 (7) | 0.0244 (8) | 0.0261 (8) | 0.0025 (6) | 0.0093 (6) | −0.0013 (6) |
C13 | 0.0199 (7) | 0.0267 (8) | 0.0227 (7) | 0.0013 (6) | 0.0046 (6) | −0.0009 (6) |
C14 | 0.0304 (8) | 0.0246 (8) | 0.0251 (8) | −0.0017 (7) | 0.0074 (7) | −0.0015 (6) |
C15 | 0.0404 (10) | 0.0328 (9) | 0.0231 (8) | 0.0005 (8) | 0.0102 (7) | 0.0035 (7) |
C16 | 0.0404 (10) | 0.0361 (10) | 0.0200 (8) | 0.0021 (8) | 0.0045 (7) | −0.0016 (7) |
C17 | 0.0369 (9) | 0.0322 (9) | 0.0271 (8) | −0.0048 (8) | 0.0035 (7) | −0.0067 (7) |
C18 | 0.0315 (9) | 0.0278 (9) | 0.0278 (8) | −0.0035 (7) | 0.0076 (7) | 0.0012 (7) |
C19 | 0.0246 (8) | 0.0245 (8) | 0.0194 (7) | 0.0008 (6) | 0.0045 (6) | 0.0022 (6) |
C20 | 0.0264 (8) | 0.0255 (8) | 0.0242 (8) | 0.0020 (7) | 0.0068 (6) | 0.0004 (6) |
C21 | 0.0254 (8) | 0.0344 (9) | 0.0246 (8) | 0.0021 (7) | 0.0087 (6) | 0.0037 (7) |
C22 | 0.0242 (8) | 0.0316 (9) | 0.0324 (9) | −0.0064 (7) | 0.0047 (7) | 0.0068 (7) |
C23 | 0.0274 (8) | 0.0239 (8) | 0.0271 (8) | 0.0006 (7) | 0.0029 (6) | 0.0000 (6) |
C24 | 0.0279 (8) | 0.0267 (8) | 0.0210 (7) | 0.0012 (7) | 0.0090 (6) | 0.0016 (6) |
C25 | 0.0418 (11) | 0.0486 (12) | 0.0519 (12) | −0.0053 (9) | 0.0283 (9) | −0.0048 (10) |
Geometric parameters (Å, º) top C1—C2 | 1.355 (2) | C13—C18 | 1.402 (2) |
C1—C5 | 1.492 (2) | C14—H14 | 0.9300 |
C1—C7 | 1.478 (2) | C14—C15 | 1.388 (2) |
C2—H2 | 0.9300 | C15—H15 | 0.9300 |
C2—C3 | 1.471 (2) | C15—C16 | 1.387 (3) |
C3—C4 | 1.354 (2) | C16—H16 | 0.9300 |
C3—C13 | 1.468 (2) | C16—C17 | 1.384 (3) |
C4—H4 | 0.9300 | C17—H17 | 0.9300 |
C4—C5 | 1.458 (2) | C17—C18 | 1.379 (2) |
C5—C6 | 1.347 (2) | C18—H18 | 0.9300 |
C6—H6 | 0.9300 | C19—C20 | 1.398 (2) |
C6—C19 | 1.469 (2) | C19—C24 | 1.403 (2) |
C7—C8 | 1.397 (2) | C20—H20 | 0.9300 |
C7—C12 | 1.404 (2) | C20—C21 | 1.383 (2) |
C8—H8 | 0.9300 | C21—C22 | 1.398 (2) |
C8—C9 | 1.387 (2) | C21—C25 | 1.511 (2) |
C9—H9 | 0.9300 | C22—H22 | 0.9300 |
C9—C10 | 1.391 (3) | C22—C23 | 1.392 (2) |
C10—H10 | 0.9300 | C23—H23 | 0.9300 |
C10—C11 | 1.386 (2) | C23—C24 | 1.380 (2) |
C11—H11 | 0.9300 | C24—H24 | 0.9300 |
C11—C12 | 1.388 (2) | C25—H25A | 0.9600 |
C12—H12 | 0.9300 | C25—H25B | 0.9600 |
C13—C14 | 1.397 (2) | C25—H25C | 0.9600 |
| | | |
C2—C1—C5 | 106.92 (13) | C13—C14—H14 | 119.7 |
C2—C1—C7 | 125.48 (14) | C15—C14—C13 | 120.67 (16) |
C7—C1—C5 | 127.55 (13) | C15—C14—H14 | 119.7 |
C1—C2—H2 | 125.0 | C14—C15—H15 | 119.8 |
C1—C2—C3 | 109.94 (14) | C16—C15—C14 | 120.40 (16) |
C3—C2—H2 | 125.0 | C16—C15—H15 | 119.8 |
C4—C3—C2 | 108.10 (14) | C15—C16—H16 | 120.3 |
C4—C3—C13 | 126.58 (14) | C17—C16—C15 | 119.43 (16) |
C13—C3—C2 | 125.28 (14) | C17—C16—H16 | 120.3 |
C3—C4—H4 | 125.4 | C16—C17—H17 | 119.8 |
C3—C4—C5 | 109.10 (14) | C18—C17—C16 | 120.43 (16) |
C5—C4—H4 | 125.4 | C18—C17—H17 | 119.8 |
C4—C5—C1 | 105.89 (13) | C13—C18—H18 | 119.5 |
C6—C5—C1 | 125.53 (14) | C17—C18—C13 | 121.01 (16) |
C6—C5—C4 | 128.10 (15) | C17—C18—H18 | 119.5 |
C5—C6—H6 | 115.9 | C20—C19—C6 | 118.51 (14) |
C5—C6—C19 | 128.29 (15) | C20—C19—C24 | 118.07 (14) |
C19—C6—H6 | 115.9 | C24—C19—C6 | 123.42 (14) |
C8—C7—C1 | 122.65 (14) | C19—C20—H20 | 118.9 |
C8—C7—C12 | 118.00 (14) | C21—C20—C19 | 122.15 (15) |
C12—C7—C1 | 119.28 (14) | C21—C20—H20 | 118.9 |
C7—C8—H8 | 119.7 | C20—C21—C22 | 118.53 (15) |
C9—C8—C7 | 120.56 (15) | C20—C21—C25 | 121.35 (16) |
C9—C8—H8 | 119.7 | C22—C21—C25 | 120.11 (16) |
C8—C9—H9 | 119.6 | C21—C22—H22 | 119.8 |
C8—C9—C10 | 120.89 (16) | C23—C22—C21 | 120.38 (15) |
C10—C9—H9 | 119.6 | C23—C22—H22 | 119.8 |
C9—C10—H10 | 120.4 | C22—C23—H23 | 119.8 |
C11—C10—C9 | 119.15 (15) | C24—C23—C22 | 120.34 (16) |
C11—C10—H10 | 120.4 | C24—C23—H23 | 119.8 |
C10—C11—H11 | 119.9 | C19—C24—H24 | 119.8 |
C10—C11—C12 | 120.22 (16) | C23—C24—C19 | 120.48 (15) |
C12—C11—H11 | 119.9 | C23—C24—H24 | 119.8 |
C7—C12—H12 | 119.4 | C21—C25—H25A | 109.5 |
C11—C12—C7 | 121.14 (15) | C21—C25—H25B | 109.5 |
C11—C12—H12 | 119.4 | C21—C25—H25C | 109.5 |
C14—C13—C3 | 120.79 (14) | H25A—C25—H25B | 109.5 |
C14—C13—C18 | 118.05 (15) | H25A—C25—H25C | 109.5 |
C18—C13—C3 | 121.16 (14) | H25B—C25—H25C | 109.5 |
Hydrogen-bond geometry (Å, º) topCg1 and Cg2 are the centroids of the C13–C18 and C19–C24 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···Cg1i | 0.93 | 2.83 | 3.539 (2) | 134 |
C16—H16···Cg2ii | 0.93 | 2.86 | 3.589 (2) | 136 |
C23—H23···Cg2iii | 0.93 | 2.90 | 3.547 (2) | 128 |
Symmetry codes: (i) −x, y−1, −z+1/2; (ii) −x+1/2, y+3/2, −z+1/2; (iii) x, −y, z−1/2. |
{3-[(4-Methylphenyl)methylidene]-4-phenylcyclopenta-1,4-dien-1-yl}benzene (II)
top Crystal data top C25H20 | F(000) = 680 |
Mr = 320.41 | Dx = 1.222 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 19.208 (2) Å | Cell parameters from 6861 reflections |
b = 5.8774 (7) Å | θ = 2.2–26.1° |
c = 16.1884 (18) Å | µ = 0.07 mm−1 |
β = 107.710 (1)° | T = 100 K |
V = 1740.9 (3) Å3 | Rect. Prism, red |
Z = 4 | 0.43 × 0.27 × 0.06 mm |
Data collection top Bruker APEXII CCD diffractometer | 2972 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.038 |
φ and ω scans | θmax = 26.2°, θmin = 2.2° |
Absorption correction: multi-scan SADABS | h = −23→23 |
Tmin = 0.691, Tmax = 0.745 | k = −7→7 |
30237 measured reflections | l = −20→20 |
3473 independent reflections | |
Refinement top Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0394P)2 + 0.8955P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3473 reflections | Δρmax = 0.22 e Å−3 |
227 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | |
Special details top Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.21805 (7) | 0.4854 (2) | 0.67244 (8) | 0.0199 (3) | |
C19 | 0.39564 (7) | 0.1392 (2) | 0.78528 (8) | 0.0196 (3) | |
C3 | 0.16408 (7) | 0.3062 (2) | 0.76451 (8) | 0.0199 (3) | |
C13 | 0.23043 (6) | 0.6328 (2) | 0.60483 (8) | 0.0199 (3) | |
C24 | 0.46911 (7) | 0.2083 (2) | 0.81558 (8) | 0.0205 (3) | |
H24 | 0.482874 | 0.351246 | 0.797988 | 0.025* | |
C6 | 0.34162 (7) | 0.2980 (2) | 0.73220 (8) | 0.0199 (3) | |
H6 | 0.358882 | 0.400502 | 0.697460 | 0.024* | |
C21 | 0.43165 (7) | −0.2155 (2) | 0.86275 (8) | 0.0217 (3) | |
H21 | 0.418584 | −0.361899 | 0.878004 | 0.026* | |
C22 | 0.50403 (7) | −0.1435 (2) | 0.89566 (8) | 0.0209 (3) | |
C23 | 0.52175 (7) | 0.0712 (2) | 0.87068 (8) | 0.0212 (3) | |
H23 | 0.570728 | 0.123926 | 0.891873 | 0.025* | |
C4 | 0.23106 (7) | 0.2078 (2) | 0.78063 (8) | 0.0205 (3) | |
H4 | 0.249483 | 0.087659 | 0.820575 | 0.025* | |
C14 | 0.27283 (7) | 0.5647 (2) | 0.55254 (8) | 0.0218 (3) | |
H14 | 0.294824 | 0.418298 | 0.560510 | 0.026* | |
C7 | 0.11136 (7) | 0.2699 (2) | 0.81300 (8) | 0.0205 (3) | |
C5 | 0.26996 (7) | 0.3166 (2) | 0.72660 (8) | 0.0195 (3) | |
C20 | 0.37819 (7) | −0.0787 (2) | 0.80827 (8) | 0.0206 (3) | |
H20 | 0.329440 | −0.133081 | 0.786414 | 0.025* | |
C2 | 0.15635 (7) | 0.4766 (2) | 0.69629 (8) | 0.0217 (3) | |
H2 | 0.114171 | 0.567633 | 0.672247 | 0.026* | |
C18 | 0.19736 (7) | 0.8485 (2) | 0.58962 (8) | 0.0229 (3) | |
H18 | 0.168610 | 0.899257 | 0.624501 | 0.027* | |
C8 | 0.11440 (7) | 0.0724 (2) | 0.86246 (8) | 0.0240 (3) | |
H8 | 0.146980 | −0.046782 | 0.859555 | 0.029* | |
C12 | 0.06039 (7) | 0.4379 (2) | 0.81513 (8) | 0.0235 (3) | |
H12 | 0.055986 | 0.569546 | 0.779883 | 0.028* | |
C17 | 0.20606 (7) | 0.9880 (2) | 0.52453 (9) | 0.0277 (3) | |
H17 | 0.181975 | 1.131132 | 0.513845 | 0.033* | |
C15 | 0.28318 (7) | 0.7086 (2) | 0.48909 (8) | 0.0256 (3) | |
H15 | 0.313325 | 0.661580 | 0.455334 | 0.031* | |
C9 | 0.07027 (7) | 0.0496 (3) | 0.91556 (9) | 0.0284 (3) | |
H9 | 0.073164 | −0.084411 | 0.949270 | 0.034* | |
C11 | 0.01606 (7) | 0.4138 (3) | 0.86843 (9) | 0.0272 (3) | |
H11 | −0.018208 | 0.529317 | 0.869678 | 0.033* | |
C16 | 0.24982 (7) | 0.9197 (2) | 0.47484 (9) | 0.0285 (3) | |
H16 | 0.256832 | 1.017343 | 0.431291 | 0.034* | |
C10 | 0.02185 (7) | 0.2213 (3) | 0.91982 (9) | 0.0289 (3) | |
H10 | −0.007197 | 0.207094 | 0.957700 | 0.035* | |
C25 | 0.56192 (7) | −0.2930 (2) | 0.95447 (9) | 0.0277 (3) | |
H25A | 0.582960 | −0.216495 | 1.010312 | 0.042* | |
H25B | 0.600443 | −0.322080 | 0.927669 | 0.042* | |
H25C | 0.539995 | −0.437632 | 0.963685 | 0.042* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0197 (6) | 0.0202 (6) | 0.0184 (6) | 0.0004 (5) | 0.0035 (5) | −0.0010 (5) |
C19 | 0.0201 (6) | 0.0221 (6) | 0.0176 (6) | 0.0027 (5) | 0.0074 (5) | −0.0014 (5) |
C3 | 0.0196 (6) | 0.0205 (6) | 0.0185 (6) | −0.0006 (5) | 0.0043 (5) | −0.0015 (5) |
C13 | 0.0158 (6) | 0.0224 (6) | 0.0188 (6) | −0.0023 (5) | 0.0013 (5) | 0.0012 (5) |
C24 | 0.0224 (6) | 0.0192 (6) | 0.0219 (6) | 0.0011 (5) | 0.0096 (5) | 0.0003 (5) |
C6 | 0.0219 (6) | 0.0201 (6) | 0.0182 (6) | 0.0004 (5) | 0.0067 (5) | −0.0004 (5) |
C21 | 0.0240 (6) | 0.0196 (6) | 0.0241 (6) | 0.0017 (5) | 0.0113 (5) | 0.0014 (5) |
C22 | 0.0220 (6) | 0.0231 (6) | 0.0190 (6) | 0.0053 (5) | 0.0084 (5) | 0.0009 (5) |
C23 | 0.0177 (6) | 0.0242 (7) | 0.0221 (6) | 0.0007 (5) | 0.0065 (5) | −0.0024 (5) |
C4 | 0.0223 (6) | 0.0200 (6) | 0.0191 (6) | 0.0009 (5) | 0.0060 (5) | 0.0006 (5) |
C14 | 0.0190 (6) | 0.0238 (7) | 0.0207 (6) | −0.0010 (5) | 0.0033 (5) | 0.0011 (5) |
C7 | 0.0174 (6) | 0.0245 (7) | 0.0180 (6) | −0.0034 (5) | 0.0030 (5) | −0.0011 (5) |
C5 | 0.0211 (6) | 0.0193 (6) | 0.0176 (6) | 0.0006 (5) | 0.0051 (5) | −0.0011 (5) |
C20 | 0.0185 (6) | 0.0215 (6) | 0.0225 (6) | 0.0005 (5) | 0.0073 (5) | −0.0015 (5) |
C2 | 0.0191 (6) | 0.0228 (7) | 0.0220 (6) | 0.0023 (5) | 0.0046 (5) | 0.0022 (5) |
C18 | 0.0195 (6) | 0.0230 (7) | 0.0242 (6) | −0.0005 (5) | 0.0038 (5) | −0.0008 (5) |
C8 | 0.0194 (6) | 0.0262 (7) | 0.0240 (6) | −0.0027 (5) | 0.0028 (5) | 0.0017 (5) |
C12 | 0.0210 (6) | 0.0252 (7) | 0.0238 (6) | −0.0014 (5) | 0.0058 (5) | 0.0008 (5) |
C17 | 0.0253 (7) | 0.0224 (7) | 0.0294 (7) | −0.0016 (6) | −0.0007 (6) | 0.0049 (6) |
C15 | 0.0214 (6) | 0.0348 (8) | 0.0196 (6) | −0.0048 (6) | 0.0046 (5) | 0.0012 (6) |
C9 | 0.0243 (7) | 0.0337 (8) | 0.0253 (7) | −0.0066 (6) | 0.0049 (5) | 0.0066 (6) |
C11 | 0.0201 (6) | 0.0338 (8) | 0.0281 (7) | −0.0009 (6) | 0.0080 (5) | −0.0042 (6) |
C16 | 0.0278 (7) | 0.0305 (8) | 0.0232 (7) | −0.0074 (6) | 0.0021 (5) | 0.0088 (6) |
C10 | 0.0211 (7) | 0.0419 (8) | 0.0249 (7) | −0.0083 (6) | 0.0091 (5) | 0.0000 (6) |
C25 | 0.0228 (7) | 0.0290 (7) | 0.0305 (7) | 0.0040 (6) | 0.0067 (6) | 0.0063 (6) |
Geometric parameters (Å, º) top C1—C13 | 1.4707 (17) | C14—C15 | 1.3906 (18) |
C1—C5 | 1.4883 (17) | C7—C8 | 1.4012 (18) |
C1—C2 | 1.3547 (18) | C7—C12 | 1.3981 (19) |
C19—C24 | 1.4057 (17) | C20—H20 | 0.9500 |
C19—C6 | 1.4642 (17) | C2—H2 | 0.9500 |
C19—C20 | 1.4023 (18) | C18—H18 | 0.9500 |
C3—C4 | 1.3616 (17) | C18—C17 | 1.3850 (19) |
C3—C7 | 1.4733 (17) | C8—H8 | 0.9500 |
C3—C2 | 1.4641 (17) | C8—C9 | 1.3850 (19) |
C13—C14 | 1.3997 (18) | C12—H12 | 0.9500 |
C13—C18 | 1.4056 (18) | C12—C11 | 1.3916 (18) |
C24—H24 | 0.9500 | C17—H17 | 0.9500 |
C24—C23 | 1.3852 (18) | C17—C16 | 1.388 (2) |
C6—H6 | 0.9500 | C15—H15 | 0.9500 |
C6—C5 | 1.3561 (17) | C15—C16 | 1.383 (2) |
C21—H21 | 0.9500 | C9—H9 | 0.9500 |
C21—C22 | 1.3946 (18) | C9—C10 | 1.388 (2) |
C21—C20 | 1.3883 (18) | C11—H11 | 0.9500 |
C22—C23 | 1.3983 (19) | C11—C10 | 1.389 (2) |
C22—C25 | 1.5068 (17) | C16—H16 | 0.9500 |
C23—H23 | 0.9500 | C10—H10 | 0.9500 |
C4—H4 | 0.9500 | C25—H25A | 0.9800 |
C4—C5 | 1.4596 (17) | C25—H25B | 0.9800 |
C14—H14 | 0.9500 | C25—H25C | 0.9800 |
| | | |
C13—C1—C5 | 126.87 (11) | C19—C20—H20 | 119.8 |
C2—C1—C13 | 126.04 (12) | C21—C20—C19 | 120.46 (12) |
C2—C1—C5 | 107.08 (11) | C21—C20—H20 | 119.8 |
C24—C19—C6 | 118.52 (12) | C1—C2—C3 | 110.16 (11) |
C20—C19—C24 | 117.84 (11) | C1—C2—H2 | 124.9 |
C20—C19—C6 | 123.64 (11) | C3—C2—H2 | 124.9 |
C4—C3—C7 | 126.77 (12) | C13—C18—H18 | 119.5 |
C4—C3—C2 | 107.96 (11) | C17—C18—C13 | 120.97 (13) |
C2—C3—C7 | 124.93 (11) | C17—C18—H18 | 119.5 |
C14—C13—C1 | 122.49 (12) | C7—C8—H8 | 119.7 |
C14—C13—C18 | 117.84 (12) | C9—C8—C7 | 120.53 (13) |
C18—C13—C1 | 119.65 (12) | C9—C8—H8 | 119.7 |
C19—C24—H24 | 119.5 | C7—C12—H12 | 119.7 |
C23—C24—C19 | 121.01 (12) | C11—C12—C7 | 120.58 (13) |
C23—C24—H24 | 119.5 | C11—C12—H12 | 119.7 |
C19—C6—H6 | 116.0 | C18—C17—H17 | 119.9 |
C5—C6—C19 | 127.90 (12) | C18—C17—C16 | 120.26 (13) |
C5—C6—H6 | 116.0 | C16—C17—H17 | 119.9 |
C22—C21—H21 | 119.1 | C14—C15—H15 | 119.8 |
C20—C21—H21 | 119.1 | C16—C15—C14 | 120.36 (13) |
C20—C21—C22 | 121.73 (12) | C16—C15—H15 | 119.8 |
C21—C22—C23 | 117.72 (12) | C8—C9—H9 | 119.8 |
C21—C22—C25 | 121.52 (12) | C8—C9—C10 | 120.40 (13) |
C23—C22—C25 | 120.74 (12) | C10—C9—H9 | 119.8 |
C24—C23—C22 | 121.14 (12) | C12—C11—H11 | 120.0 |
C24—C23—H23 | 119.4 | C10—C11—C12 | 120.09 (13) |
C22—C23—H23 | 119.4 | C10—C11—H11 | 120.0 |
C3—C4—H4 | 125.5 | C17—C16—H16 | 120.2 |
C3—C4—C5 | 108.96 (11) | C15—C16—C17 | 119.64 (13) |
C5—C4—H4 | 125.5 | C15—C16—H16 | 120.2 |
C13—C14—H14 | 119.6 | C9—C10—C11 | 119.70 (13) |
C15—C14—C13 | 120.87 (13) | C9—C10—H10 | 120.2 |
C15—C14—H14 | 119.6 | C11—C10—H10 | 120.2 |
C8—C7—C3 | 120.58 (12) | C22—C25—H25A | 109.5 |
C12—C7—C3 | 120.70 (12) | C22—C25—H25B | 109.5 |
C12—C7—C8 | 118.59 (12) | C22—C25—H25C | 109.5 |
C6—C5—C1 | 125.28 (12) | H25A—C25—H25B | 109.5 |
C6—C5—C4 | 128.23 (12) | H25A—C25—H25C | 109.5 |
C4—C5—C1 | 105.78 (10) | H25B—C25—H25C | 109.5 |
Hydrogen-bond geometry (Å, º) topCg3 and Cg4 are the centroids of the C7–C12 and C19–C24 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···Cg3i | 0.95 | 2.95 | 3.6560 (4) | 132 |
C17—H17···Cg3ii | 0.95 | 2.83 | 3.4837 (4) | 127 |
C25—H25A···Cg4iii | 0.98 | 2.98 | 3.8277 (4) | 145 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, −y−3/2, z−3/2; (iii) −x+1, −y+1, −z+1. |
{3-[(2,4,6-Trimethylphenyl)methylidene]-4-phenylcyclopenta-1,4-dien-1-yl}benzene (III)
top Crystal data top C27H24 | Dx = 1.169 Mg m−3 |
Mr = 348.46 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 3728 reflections |
a = 30.031 (6) Å | θ = 2.2–22.3° |
b = 5.6147 (12) Å | µ = 0.07 mm−1 |
c = 23.494 (5) Å | T = 100 K |
V = 3961.4 (14) Å3 | Irregular, red |
Z = 8 | 0.26 × 0.11 × 0.10 mm |
F(000) = 1488 | |
Data collection top Bruker APEXII CCD diffractometer | 5709 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.070 |
Absorption correction: multi-scan SADABS | θmax = 24.8°, θmin = 2.2° |
Tmin = 0.678, Tmax = 0.745 | h = −35→35 |
38475 measured reflections | k = −6→6 |
6776 independent reflections | l = −27→27 |
Refinement top Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.054P)2 + 0.3457P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.108 | (Δ/σ)max = 0.001 |
S = 1.03 | Δρmax = 0.17 e Å−3 |
6776 reflections | Δρmin = −0.17 e Å−3 |
494 parameters | Absolute structure: Refined as an inversion twin. |
1 restraint | Absolute structure parameter: −6 (10) |
Primary atom site location: dual | |
Special details top Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a two-component inversion twin |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.35712 (11) | 0.1134 (6) | 0.54077 (15) | 0.0224 (8) | |
C2 | 0.36382 (11) | 0.1309 (6) | 0.48394 (15) | 0.0238 (8) | |
H2 | 0.384904 | 0.045102 | 0.463428 | 0.029* | |
C3 | 0.33274 (11) | 0.3060 (6) | 0.45947 (15) | 0.0219 (8) | |
C4 | 0.30771 (12) | 0.3951 (6) | 0.50228 (15) | 0.0230 (8) | |
H4 | 0.286286 | 0.513761 | 0.498702 | 0.028* | |
C5 | 0.31988 (11) | 0.2742 (6) | 0.55511 (15) | 0.0227 (8) | |
C6 | 0.29829 (11) | 0.2883 (6) | 0.60543 (15) | 0.0239 (8) | |
H6 | 0.308796 | 0.193941 | 0.635065 | 0.029* | |
C7 | 0.38365 (11) | −0.0333 (6) | 0.58024 (14) | 0.0225 (8) | |
C8 | 0.39541 (11) | 0.0453 (6) | 0.63499 (15) | 0.0245 (8) | |
H8 | 0.385132 | 0.191708 | 0.648020 | 0.029* | |
C9 | 0.42211 (12) | −0.0930 (6) | 0.66963 (16) | 0.0274 (8) | |
H9 | 0.429090 | −0.040616 | 0.706110 | 0.033* | |
C10 | 0.43847 (12) | −0.3077 (7) | 0.65055 (17) | 0.0283 (9) | |
H10 | 0.456900 | −0.398471 | 0.673806 | 0.034* | |
C11 | 0.42743 (12) | −0.3879 (6) | 0.59677 (16) | 0.0265 (9) | |
H11 | 0.438662 | −0.532334 | 0.583768 | 0.032* | |
C12 | 0.39980 (11) | −0.2547 (6) | 0.56223 (15) | 0.0227 (8) | |
H12 | 0.391827 | −0.312675 | 0.526587 | 0.027* | |
C13 | 0.33002 (11) | 0.3610 (6) | 0.39856 (15) | 0.0216 (8) | |
C14 | 0.34639 (11) | 0.1972 (6) | 0.35861 (14) | 0.0243 (8) | |
H14 | 0.359649 | 0.057076 | 0.371174 | 0.029* | |
C15 | 0.34310 (12) | 0.2409 (6) | 0.30085 (16) | 0.0284 (8) | |
H15 | 0.354276 | 0.130280 | 0.275078 | 0.034* | |
C16 | 0.32342 (12) | 0.4469 (7) | 0.28105 (16) | 0.0282 (8) | |
H16 | 0.321116 | 0.475127 | 0.242154 | 0.034* | |
C17 | 0.30710 (12) | 0.6115 (7) | 0.31990 (16) | 0.0291 (9) | |
H17 | 0.293684 | 0.750470 | 0.306878 | 0.035* | |
C18 | 0.31060 (11) | 0.5705 (6) | 0.37800 (15) | 0.0249 (8) | |
H18 | 0.299935 | 0.683511 | 0.403522 | 0.030* | |
C19 | 0.25933 (11) | 0.4412 (6) | 0.61723 (14) | 0.0226 (8) | |
C20 | 0.26414 (11) | 0.6213 (6) | 0.65876 (14) | 0.0240 (8) | |
C21 | 0.22874 (12) | 0.7743 (6) | 0.66946 (15) | 0.0252 (8) | |
H21 | 0.232343 | 0.897102 | 0.695611 | 0.030* | |
C22 | 0.18814 (12) | 0.7477 (6) | 0.64199 (15) | 0.0249 (8) | |
C23 | 0.18351 (11) | 0.5641 (6) | 0.60303 (15) | 0.0248 (8) | |
H23 | 0.156118 | 0.542375 | 0.585313 | 0.030* | |
C24 | 0.21846 (12) | 0.4107 (6) | 0.58945 (14) | 0.0232 (8) | |
C25 | 0.30762 (12) | 0.6478 (7) | 0.69049 (16) | 0.0324 (9) | |
H25A | 0.312022 | 0.512148 | 0.714713 | 0.049* | |
H25B | 0.306771 | 0.789870 | 0.713210 | 0.049* | |
H25C | 0.331689 | 0.658303 | 0.663719 | 0.049* | |
C26 | 0.14909 (12) | 0.9077 (7) | 0.65542 (17) | 0.0334 (9) | |
H26A | 0.132792 | 0.843321 | 0.687025 | 0.050* | |
H26B | 0.129912 | 0.917565 | 0.622806 | 0.050* | |
H26C | 0.159736 | 1.063905 | 0.664950 | 0.050* | |
C27 | 0.21031 (12) | 0.2158 (7) | 0.54676 (16) | 0.0297 (9) | |
H27A | 0.217207 | 0.272939 | 0.509273 | 0.044* | |
H27B | 0.179610 | 0.168474 | 0.548256 | 0.044* | |
H27C | 0.228897 | 0.081633 | 0.555521 | 0.044* | |
C28 | 0.51786 (11) | 0.0968 (6) | 0.46548 (15) | 0.0224 (8) | |
C29 | 0.51122 (12) | 0.1276 (6) | 0.52183 (15) | 0.0239 (8) | |
H29 | 0.490034 | 0.047263 | 0.543401 | 0.029* | |
C30 | 0.54251 (11) | 0.3073 (6) | 0.54415 (15) | 0.0218 (8) | |
C31 | 0.56796 (12) | 0.3832 (6) | 0.50028 (16) | 0.0225 (7) | |
H31 | 0.589866 | 0.499884 | 0.502582 | 0.027* | |
C32 | 0.55572 (11) | 0.2536 (6) | 0.44875 (15) | 0.0229 (8) | |
C33 | 0.57550 (11) | 0.2587 (6) | 0.39746 (15) | 0.0243 (8) | |
H33 | 0.564527 | 0.155088 | 0.369957 | 0.029* | |
C34 | 0.49026 (11) | −0.0516 (6) | 0.42789 (15) | 0.0223 (8) | |
C35 | 0.47587 (11) | 0.0308 (6) | 0.37476 (15) | 0.0246 (8) | |
H35 | 0.486290 | 0.175537 | 0.360834 | 0.030* | |
C36 | 0.44609 (12) | −0.1027 (6) | 0.34279 (16) | 0.0278 (9) | |
H36 | 0.436917 | −0.047288 | 0.307383 | 0.033* | |
C37 | 0.42992 (12) | −0.3171 (7) | 0.36296 (16) | 0.0297 (9) | |
H37 | 0.409495 | −0.403887 | 0.341633 | 0.036* | |
C38 | 0.44434 (12) | −0.4018 (7) | 0.41514 (17) | 0.0286 (9) | |
H38 | 0.433815 | −0.546723 | 0.428766 | 0.034* | |
C39 | 0.47439 (11) | −0.2711 (6) | 0.44707 (16) | 0.0245 (8) | |
H39 | 0.484165 | −0.330463 | 0.481852 | 0.029* | |
C40 | 0.54362 (11) | 0.3803 (6) | 0.60410 (15) | 0.0217 (8) | |
C41 | 0.56288 (11) | 0.5974 (7) | 0.62138 (15) | 0.0248 (8) | |
H41 | 0.574388 | 0.700735 | 0.594173 | 0.030* | |
C42 | 0.56484 (12) | 0.6580 (7) | 0.67802 (16) | 0.0267 (9) | |
H42 | 0.578045 | 0.800994 | 0.688734 | 0.032* | |
C43 | 0.54749 (12) | 0.5096 (6) | 0.71904 (16) | 0.0278 (9) | |
H43 | 0.548967 | 0.551985 | 0.757264 | 0.033* | |
C44 | 0.52781 (11) | 0.2968 (6) | 0.70301 (15) | 0.0253 (8) | |
H44 | 0.516058 | 0.195981 | 0.730586 | 0.030* | |
C45 | 0.52556 (11) | 0.2335 (6) | 0.64608 (15) | 0.0234 (8) | |
H45 | 0.511850 | 0.091446 | 0.635730 | 0.028* | |
C46 | 0.61314 (11) | 0.4139 (6) | 0.38060 (14) | 0.0223 (8) | |
C47 | 0.65574 (11) | 0.3931 (6) | 0.40497 (14) | 0.0241 (8) | |
C48 | 0.68915 (12) | 0.5477 (6) | 0.38677 (16) | 0.0278 (9) | |
H48 | 0.717337 | 0.534982 | 0.402891 | 0.033* | |
C49 | 0.68188 (12) | 0.7189 (7) | 0.34564 (16) | 0.0280 (9) | |
C50 | 0.63963 (12) | 0.7337 (7) | 0.32137 (16) | 0.0293 (9) | |
H50 | 0.634253 | 0.847371 | 0.293421 | 0.035* | |
C51 | 0.60570 (12) | 0.5842 (7) | 0.33773 (15) | 0.0269 (8) | |
C52 | 0.66681 (12) | 0.2043 (7) | 0.44841 (16) | 0.0309 (9) | |
H52A | 0.657021 | 0.255505 | 0.485335 | 0.046* | |
H52B | 0.698413 | 0.178763 | 0.449049 | 0.046* | |
H52C | 0.652035 | 0.058469 | 0.438490 | 0.046* | |
C53 | 0.71847 (13) | 0.8856 (7) | 0.32675 (19) | 0.0387 (10) | |
H53A | 0.743758 | 0.867604 | 0.351372 | 0.058* | |
H53B | 0.707971 | 1.046960 | 0.328511 | 0.058* | |
H53C | 0.726934 | 0.848305 | 0.288375 | 0.058* | |
C54 | 0.56037 (13) | 0.6030 (8) | 0.31041 (18) | 0.0379 (11) | |
H54A | 0.553643 | 0.457151 | 0.290898 | 0.057* | |
H54B | 0.560283 | 0.732458 | 0.283720 | 0.057* | |
H54C | 0.538341 | 0.631357 | 0.339236 | 0.057* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0209 (18) | 0.0218 (18) | 0.024 (2) | 0.0005 (15) | 0.0000 (15) | 0.0015 (15) |
C2 | 0.0235 (19) | 0.0217 (19) | 0.026 (2) | 0.0025 (15) | 0.0021 (16) | −0.0005 (15) |
C3 | 0.0194 (18) | 0.0227 (18) | 0.024 (2) | 0.0005 (15) | 0.0014 (15) | 0.0014 (15) |
C4 | 0.0218 (18) | 0.0215 (17) | 0.026 (2) | 0.0006 (15) | 0.0007 (15) | 0.0027 (15) |
C5 | 0.0232 (18) | 0.0238 (18) | 0.021 (2) | −0.0012 (15) | 0.0015 (15) | −0.0014 (15) |
C6 | 0.025 (2) | 0.0218 (18) | 0.024 (2) | 0.0012 (15) | 0.0000 (15) | 0.0042 (15) |
C7 | 0.0178 (18) | 0.0255 (18) | 0.024 (2) | −0.0006 (14) | 0.0032 (15) | 0.0024 (16) |
C8 | 0.0217 (19) | 0.0255 (19) | 0.026 (2) | −0.0013 (16) | 0.0035 (15) | −0.0010 (15) |
C9 | 0.0249 (19) | 0.033 (2) | 0.024 (2) | −0.0015 (17) | −0.0045 (16) | 0.0000 (16) |
C10 | 0.023 (2) | 0.028 (2) | 0.034 (2) | −0.0005 (16) | −0.0048 (16) | 0.0067 (18) |
C11 | 0.0246 (19) | 0.0224 (19) | 0.033 (2) | 0.0018 (15) | 0.0059 (17) | 0.0008 (16) |
C12 | 0.0218 (18) | 0.0229 (18) | 0.0233 (19) | −0.0002 (15) | 0.0012 (15) | 0.0013 (14) |
C13 | 0.0159 (18) | 0.0250 (18) | 0.024 (2) | −0.0023 (14) | 0.0020 (14) | 0.0008 (14) |
C14 | 0.022 (2) | 0.0250 (18) | 0.026 (2) | 0.0012 (16) | 0.0016 (15) | 0.0008 (15) |
C15 | 0.0273 (19) | 0.030 (2) | 0.028 (2) | 0.0013 (16) | 0.0027 (16) | −0.0023 (16) |
C16 | 0.030 (2) | 0.033 (2) | 0.022 (2) | −0.0028 (17) | 0.0019 (16) | 0.0058 (16) |
C17 | 0.027 (2) | 0.031 (2) | 0.029 (2) | 0.0029 (17) | −0.0010 (16) | 0.0074 (17) |
C18 | 0.0204 (18) | 0.0273 (19) | 0.027 (2) | 0.0004 (16) | 0.0011 (15) | 0.0026 (16) |
C19 | 0.0205 (18) | 0.0255 (19) | 0.0218 (19) | 0.0006 (15) | 0.0038 (14) | 0.0049 (15) |
C20 | 0.0234 (19) | 0.0287 (19) | 0.020 (2) | −0.0038 (15) | 0.0025 (15) | 0.0024 (15) |
C21 | 0.029 (2) | 0.0262 (19) | 0.0208 (19) | −0.0031 (16) | 0.0045 (16) | −0.0011 (15) |
C22 | 0.0245 (19) | 0.0249 (19) | 0.025 (2) | 0.0004 (16) | 0.0049 (16) | 0.0018 (15) |
C23 | 0.0200 (18) | 0.0301 (19) | 0.024 (2) | −0.0034 (15) | −0.0018 (15) | 0.0033 (16) |
C24 | 0.0276 (19) | 0.0245 (18) | 0.0176 (19) | −0.0023 (15) | 0.0012 (15) | 0.0029 (15) |
C25 | 0.028 (2) | 0.038 (2) | 0.031 (2) | −0.0038 (18) | 0.0002 (17) | −0.0023 (18) |
C26 | 0.028 (2) | 0.034 (2) | 0.038 (2) | 0.0049 (18) | 0.0055 (18) | −0.0015 (18) |
C27 | 0.027 (2) | 0.035 (2) | 0.027 (2) | −0.0030 (17) | −0.0005 (17) | −0.0029 (17) |
C28 | 0.0218 (18) | 0.0222 (18) | 0.023 (2) | −0.0003 (15) | −0.0001 (15) | −0.0016 (15) |
C29 | 0.0216 (19) | 0.0259 (19) | 0.024 (2) | −0.0019 (15) | 0.0032 (15) | 0.0028 (15) |
C30 | 0.0209 (19) | 0.0213 (18) | 0.023 (2) | −0.0001 (15) | −0.0021 (15) | −0.0006 (15) |
C31 | 0.0212 (18) | 0.0220 (16) | 0.0242 (19) | −0.0022 (16) | −0.0033 (14) | −0.0014 (17) |
C32 | 0.0203 (18) | 0.0241 (19) | 0.024 (2) | 0.0014 (15) | −0.0003 (15) | 0.0011 (14) |
C33 | 0.0201 (19) | 0.031 (2) | 0.022 (2) | 0.0037 (16) | −0.0020 (15) | −0.0030 (16) |
C34 | 0.0201 (18) | 0.0234 (18) | 0.0235 (19) | 0.0018 (15) | 0.0029 (15) | −0.0035 (15) |
C35 | 0.0213 (19) | 0.0252 (18) | 0.027 (2) | 0.0003 (15) | 0.0023 (15) | −0.0038 (16) |
C36 | 0.0229 (19) | 0.035 (2) | 0.025 (2) | 0.0047 (17) | 0.0005 (16) | −0.0074 (16) |
C37 | 0.0205 (19) | 0.035 (2) | 0.034 (2) | −0.0042 (17) | 0.0019 (16) | −0.0136 (18) |
C38 | 0.0235 (19) | 0.025 (2) | 0.038 (2) | −0.0033 (16) | 0.0050 (17) | −0.0067 (17) |
C39 | 0.0211 (18) | 0.028 (2) | 0.024 (2) | −0.0001 (15) | 0.0024 (15) | −0.0016 (15) |
C40 | 0.0195 (18) | 0.0255 (19) | 0.0200 (19) | 0.0028 (15) | −0.0020 (15) | −0.0003 (15) |
C41 | 0.0234 (19) | 0.0266 (19) | 0.024 (2) | −0.0042 (15) | 0.0003 (15) | 0.0033 (15) |
C42 | 0.025 (2) | 0.027 (2) | 0.028 (2) | −0.0017 (16) | −0.0009 (16) | −0.0023 (16) |
C43 | 0.025 (2) | 0.037 (2) | 0.022 (2) | 0.0038 (17) | −0.0031 (15) | −0.0020 (17) |
C44 | 0.0213 (18) | 0.034 (2) | 0.020 (2) | 0.0024 (16) | 0.0010 (15) | 0.0040 (16) |
C45 | 0.0186 (19) | 0.0277 (19) | 0.024 (2) | −0.0007 (15) | −0.0008 (15) | 0.0010 (16) |
C46 | 0.0243 (19) | 0.0253 (19) | 0.0172 (19) | −0.0003 (15) | 0.0020 (15) | −0.0018 (15) |
C47 | 0.0215 (19) | 0.028 (2) | 0.023 (2) | 0.0029 (16) | 0.0035 (15) | 0.0007 (15) |
C48 | 0.0195 (19) | 0.031 (2) | 0.033 (2) | 0.0033 (16) | 0.0000 (16) | −0.0014 (17) |
C49 | 0.023 (2) | 0.028 (2) | 0.032 (2) | 0.0012 (16) | 0.0062 (16) | 0.0000 (17) |
C50 | 0.028 (2) | 0.031 (2) | 0.028 (2) | 0.0054 (17) | 0.0064 (16) | 0.0085 (16) |
C51 | 0.0230 (19) | 0.034 (2) | 0.024 (2) | 0.0043 (16) | 0.0009 (15) | 0.0014 (16) |
C52 | 0.025 (2) | 0.035 (2) | 0.032 (2) | 0.0035 (17) | −0.0031 (17) | 0.0060 (17) |
C53 | 0.033 (2) | 0.035 (2) | 0.047 (3) | −0.0041 (18) | 0.0066 (19) | 0.009 (2) |
C54 | 0.028 (2) | 0.049 (3) | 0.037 (3) | −0.0001 (19) | −0.0065 (18) | 0.014 (2) |
Geometric parameters (Å, º) top C1—C2 | 1.354 (5) | C28—C29 | 1.350 (5) |
C1—C5 | 1.476 (5) | C28—C32 | 1.491 (5) |
C1—C7 | 1.474 (5) | C28—C34 | 1.470 (5) |
C2—H2 | 0.9300 | C29—H29 | 0.9300 |
C2—C3 | 1.473 (5) | C29—C30 | 1.475 (5) |
C3—C4 | 1.352 (5) | C30—C31 | 1.352 (5) |
C3—C13 | 1.466 (5) | C30—C40 | 1.467 (5) |
C4—H4 | 0.9300 | C31—H31 | 0.9300 |
C4—C5 | 1.461 (5) | C31—C32 | 1.460 (5) |
C5—C6 | 1.351 (5) | C32—C33 | 1.344 (5) |
C6—H6 | 0.9300 | C33—H33 | 0.9300 |
C6—C19 | 1.478 (5) | C33—C46 | 1.481 (5) |
C7—C8 | 1.405 (5) | C34—C35 | 1.400 (5) |
C7—C12 | 1.400 (5) | C34—C39 | 1.396 (5) |
C8—H8 | 0.9300 | C35—H35 | 0.9300 |
C8—C9 | 1.381 (5) | C35—C36 | 1.388 (5) |
C9—H9 | 0.9300 | C36—H36 | 0.9300 |
C9—C10 | 1.377 (5) | C36—C37 | 1.382 (5) |
C10—H10 | 0.9300 | C37—H37 | 0.9300 |
C10—C11 | 1.382 (6) | C37—C38 | 1.384 (5) |
C11—H11 | 0.9300 | C38—H38 | 0.9300 |
C11—C12 | 1.381 (5) | C38—C39 | 1.384 (5) |
C12—H12 | 0.9300 | C39—H39 | 0.9300 |
C13—C14 | 1.403 (5) | C40—C41 | 1.409 (5) |
C13—C18 | 1.399 (5) | C40—C45 | 1.395 (5) |
C14—H14 | 0.9300 | C41—H41 | 0.9300 |
C14—C15 | 1.382 (5) | C41—C42 | 1.375 (5) |
C15—H15 | 0.9300 | C42—H42 | 0.9300 |
C15—C16 | 1.380 (5) | C42—C43 | 1.376 (5) |
C16—H16 | 0.9300 | C43—H43 | 0.9300 |
C16—C17 | 1.388 (5) | C43—C44 | 1.385 (5) |
C17—H17 | 0.9300 | C44—H44 | 0.9300 |
C17—C18 | 1.388 (5) | C44—C45 | 1.386 (5) |
C18—H18 | 0.9300 | C45—H45 | 0.9300 |
C19—C20 | 1.412 (5) | C46—C47 | 1.407 (5) |
C19—C24 | 1.401 (5) | C46—C51 | 1.407 (5) |
C20—C21 | 1.390 (5) | C47—C48 | 1.394 (5) |
C20—C25 | 1.511 (5) | C47—C52 | 1.509 (5) |
C21—H21 | 0.9300 | C48—H48 | 0.9300 |
C21—C22 | 1.388 (5) | C48—C49 | 1.381 (5) |
C22—C23 | 1.386 (5) | C49—C50 | 1.393 (5) |
C22—C26 | 1.510 (5) | C49—C53 | 1.510 (5) |
C23—H23 | 0.9300 | C50—H50 | 0.9300 |
C23—C24 | 1.395 (5) | C50—C51 | 1.375 (5) |
C24—C27 | 1.505 (5) | C51—C54 | 1.509 (5) |
C25—H25A | 0.9600 | C52—H52A | 0.9600 |
C25—H25B | 0.9600 | C52—H52B | 0.9600 |
C25—H25C | 0.9600 | C52—H52C | 0.9600 |
C26—H26A | 0.9600 | C53—H53A | 0.9600 |
C26—H26B | 0.9600 | C53—H53B | 0.9600 |
C26—H26C | 0.9600 | C53—H53C | 0.9600 |
C27—H27A | 0.9600 | C54—H54A | 0.9600 |
C27—H27B | 0.9600 | C54—H54B | 0.9600 |
C27—H27C | 0.9600 | C54—H54C | 0.9600 |
| | | |
C2—C1—C5 | 107.1 (3) | C29—C28—C32 | 107.2 (3) |
C2—C1—C7 | 125.5 (3) | C29—C28—C34 | 125.3 (3) |
C7—C1—C5 | 127.4 (3) | C34—C28—C32 | 127.3 (3) |
C1—C2—H2 | 125.1 | C28—C29—H29 | 125.0 |
C1—C2—C3 | 109.8 (3) | C28—C29—C30 | 110.0 (3) |
C3—C2—H2 | 125.1 | C30—C29—H29 | 125.0 |
C4—C3—C2 | 108.0 (3) | C31—C30—C29 | 107.7 (3) |
C4—C3—C13 | 128.1 (3) | C31—C30—C40 | 129.1 (3) |
C13—C3—C2 | 123.9 (3) | C40—C30—C29 | 123.1 (3) |
C3—C4—H4 | 125.6 | C30—C31—H31 | 125.3 |
C3—C4—C5 | 108.7 (3) | C30—C31—C32 | 109.4 (3) |
C5—C4—H4 | 125.6 | C32—C31—H31 | 125.3 |
C4—C5—C1 | 106.2 (3) | C31—C32—C28 | 105.5 (3) |
C6—C5—C1 | 126.8 (3) | C33—C32—C28 | 125.9 (3) |
C6—C5—C4 | 126.6 (3) | C33—C32—C31 | 128.4 (3) |
C5—C6—H6 | 117.3 | C32—C33—H33 | 116.9 |
C5—C6—C19 | 125.3 (3) | C32—C33—C46 | 126.2 (3) |
C19—C6—H6 | 117.3 | C46—C33—H33 | 116.9 |
C8—C7—C1 | 122.4 (3) | C35—C34—C28 | 121.5 (3) |
C12—C7—C1 | 119.6 (3) | C39—C34—C28 | 119.9 (3) |
C12—C7—C8 | 117.9 (3) | C39—C34—C35 | 118.3 (3) |
C7—C8—H8 | 119.7 | C34—C35—H35 | 119.9 |
C9—C8—C7 | 120.6 (3) | C36—C35—C34 | 120.2 (3) |
C9—C8—H8 | 119.7 | C36—C35—H35 | 119.9 |
C8—C9—H9 | 119.8 | C35—C36—H36 | 119.6 |
C10—C9—C8 | 120.5 (4) | C37—C36—C35 | 120.8 (4) |
C10—C9—H9 | 119.8 | C37—C36—H36 | 119.6 |
C9—C10—H10 | 120.1 | C36—C37—H37 | 120.2 |
C9—C10—C11 | 119.8 (4) | C36—C37—C38 | 119.5 (3) |
C11—C10—H10 | 120.1 | C38—C37—H37 | 120.2 |
C10—C11—H11 | 119.8 | C37—C38—H38 | 119.9 |
C12—C11—C10 | 120.3 (3) | C39—C38—C37 | 120.1 (4) |
C12—C11—H11 | 119.8 | C39—C38—H38 | 119.9 |
C7—C12—H12 | 119.6 | C34—C39—H39 | 119.5 |
C11—C12—C7 | 120.8 (3) | C38—C39—C34 | 121.0 (3) |
C11—C12—H12 | 119.6 | C38—C39—H39 | 119.5 |
C14—C13—C3 | 119.7 (3) | C41—C40—C30 | 121.8 (3) |
C18—C13—C3 | 122.5 (3) | C45—C40—C30 | 120.3 (3) |
C18—C13—C14 | 117.8 (3) | C45—C40—C41 | 117.8 (3) |
C13—C14—H14 | 119.5 | C40—C41—H41 | 119.6 |
C15—C14—C13 | 121.0 (3) | C42—C41—C40 | 120.7 (3) |
C15—C14—H14 | 119.5 | C42—C41—H41 | 119.6 |
C14—C15—H15 | 119.7 | C41—C42—H42 | 119.6 |
C16—C15—C14 | 120.7 (4) | C41—C42—C43 | 120.8 (3) |
C16—C15—H15 | 119.7 | C43—C42—H42 | 119.6 |
C15—C16—H16 | 120.4 | C42—C43—H43 | 120.2 |
C15—C16—C17 | 119.2 (4) | C42—C43—C44 | 119.6 (3) |
C17—C16—H16 | 120.4 | C44—C43—H43 | 120.2 |
C16—C17—H17 | 119.7 | C43—C44—H44 | 119.8 |
C16—C17—C18 | 120.6 (3) | C43—C44—C45 | 120.3 (3) |
C18—C17—H17 | 119.7 | C45—C44—H44 | 119.8 |
C13—C18—H18 | 119.6 | C40—C45—H45 | 119.6 |
C17—C18—C13 | 120.7 (3) | C44—C45—C40 | 120.8 (3) |
C17—C18—H18 | 119.6 | C44—C45—H45 | 119.6 |
C20—C19—C6 | 117.7 (3) | C47—C46—C33 | 122.4 (3) |
C24—C19—C6 | 122.4 (3) | C47—C46—C51 | 119.5 (3) |
C24—C19—C20 | 119.9 (3) | C51—C46—C33 | 118.1 (3) |
C19—C20—C25 | 120.0 (3) | C46—C47—C52 | 122.3 (3) |
C21—C20—C19 | 119.3 (3) | C48—C47—C46 | 118.6 (3) |
C21—C20—C25 | 120.7 (3) | C48—C47—C52 | 119.1 (3) |
C20—C21—H21 | 119.3 | C47—C48—H48 | 118.8 |
C22—C21—C20 | 121.5 (3) | C49—C48—C47 | 122.3 (3) |
C22—C21—H21 | 119.3 | C49—C48—H48 | 118.8 |
C21—C22—C26 | 121.4 (3) | C48—C49—C50 | 118.2 (3) |
C23—C22—C21 | 118.4 (3) | C48—C49—C53 | 121.5 (3) |
C23—C22—C26 | 120.2 (3) | C50—C49—C53 | 120.4 (3) |
C22—C23—H23 | 118.8 | C49—C50—H50 | 119.2 |
C22—C23—C24 | 122.4 (3) | C51—C50—C49 | 121.6 (3) |
C24—C23—H23 | 118.8 | C51—C50—H50 | 119.2 |
C19—C24—C27 | 122.8 (3) | C46—C51—C54 | 119.7 (3) |
C23—C24—C19 | 118.5 (3) | C50—C51—C46 | 119.8 (3) |
C23—C24—C27 | 118.6 (3) | C50—C51—C54 | 120.5 (3) |
C20—C25—H25A | 109.5 | C47—C52—H52A | 109.5 |
C20—C25—H25B | 109.5 | C47—C52—H52B | 109.5 |
C20—C25—H25C | 109.5 | C47—C52—H52C | 109.5 |
H25A—C25—H25B | 109.5 | H52A—C52—H52B | 109.5 |
H25A—C25—H25C | 109.5 | H52A—C52—H52C | 109.5 |
H25B—C25—H25C | 109.5 | H52B—C52—H52C | 109.5 |
C22—C26—H26A | 109.5 | C49—C53—H53A | 109.5 |
C22—C26—H26B | 109.5 | C49—C53—H53B | 109.5 |
C22—C26—H26C | 109.5 | C49—C53—H53C | 109.5 |
H26A—C26—H26B | 109.5 | H53A—C53—H53B | 109.5 |
H26A—C26—H26C | 109.5 | H53A—C53—H53C | 109.5 |
H26B—C26—H26C | 109.5 | H53B—C53—H53C | 109.5 |
C24—C27—H27A | 109.5 | C51—C54—H54A | 109.5 |
C24—C27—H27B | 109.5 | C51—C54—H54B | 109.5 |
C24—C27—H27C | 109.5 | C51—C54—H54C | 109.5 |
H27A—C27—H27B | 109.5 | H54A—C54—H54B | 109.5 |
H27A—C27—H27C | 109.5 | H54A—C54—H54C | 109.5 |
H27B—C27—H27C | 109.5 | H54B—C54—H54C | 109.5 |
Hydrogen-bond geometry (Å, º) topCg5, Cg6, Cg7, Cg8, and Cg9 are the centroids of the C40–C45, C7–C12, C13–C18, C28–C32, and C34–C39 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···Cg5i | 0.93 | 2.81 | 3.5059 (7) | 132 |
C25—H25C···Cg6ii | 0.96 | 2.81 | 3.7115 (8) | 158 |
C37—H37···Cg7iii | 0.93 | 2.71 | 3.5129 (8) | 145 |
C39—H39···Cg8ii | 0.93 | 2.97 | 3.5817 (8) | 125 |
C53—H53A···Cg7iv | 0.96 | 2.94 | 3.6503 (8) | 132 |
C54—H54C···Cg9v | 0.96 | 2.88 | 3.7983 (8) | 160 |
Symmetry codes: (i) −x, −y, z−1/2; (ii) x, y+1, z; (iii) −x, −y+2, z+1/2; (iv) x+1/2, −y, z; (v) x, y−1, z. |
{3-[(2,3,4,5,6-Pentamethylphenyl)methylidene]-4-phenylcyclopenta-1,4-dien-1-yl}benzene (IV)
top Crystal data top C29H28 | F(000) = 1616 |
Mr = 376.51 | Dx = 1.183 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 30.987 (7) Å | Cell parameters from 3475 reflections |
b = 5.8273 (14) Å | θ = 2.3–26.2° |
c = 23.557 (6) Å | µ = 0.07 mm−1 |
β = 96.192 (3)° | T = 100 K |
V = 4228.9 (17) Å3 | Needle, orange |
Z = 8 | 0.44 × 0.11 × 0.1 mm |
Data collection top Bruker APEXII CCD diffractometer | 3213 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.082 |
Absorption correction: multi-scan SADABS | θmax = 26.5°, θmin = 2.1° |
Tmin = 0.587, Tmax = 0.745 | h = −38→38 |
37965 measured reflections | k = −7→7 |
4394 independent reflections | l = −29→29 |
Refinement top Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0562P)2 + 4.4117P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
4394 reflections | Δρmax = 0.24 e Å−3 |
267 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | |
Special details top Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C13 | 0.59242 (5) | 0.5116 (3) | 0.64414 (7) | 0.0214 (4) | |
C7 | 0.55646 (5) | 0.0887 (3) | 0.82183 (7) | 0.0213 (4) | |
C19 | 0.67937 (5) | 0.5436 (3) | 0.86724 (7) | 0.0214 (4) | |
C5 | 0.61684 (5) | 0.3893 (3) | 0.79995 (7) | 0.0221 (4) | |
C20 | 0.67537 (6) | 0.7194 (3) | 0.90741 (7) | 0.0221 (4) | |
C4 | 0.62469 (6) | 0.5125 (3) | 0.74821 (7) | 0.0228 (4) | |
H4 | 0.646359 | 0.626148 | 0.745542 | 0.027* | |
C14 | 0.57411 (6) | 0.3657 (3) | 0.60104 (7) | 0.0242 (4) | |
H14 | 0.563145 | 0.220269 | 0.610728 | 0.029* | |
C12 | 0.54703 (5) | 0.1649 (3) | 0.87570 (7) | 0.0229 (4) | |
H12 | 0.556500 | 0.312444 | 0.888929 | 0.027* | |
C8 | 0.54204 (5) | −0.1290 (3) | 0.80385 (7) | 0.0233 (4) | |
H8 | 0.548662 | −0.185405 | 0.767949 | 0.028* | |
C3 | 0.59587 (5) | 0.4381 (3) | 0.70428 (7) | 0.0216 (4) | |
C1 | 0.57895 (5) | 0.2366 (3) | 0.78360 (7) | 0.0222 (4) | |
C2 | 0.56767 (5) | 0.2650 (3) | 0.72698 (7) | 0.0221 (4) | |
H2 | 0.544904 | 0.185041 | 0.705081 | 0.026* | |
C18 | 0.60730 (6) | 0.7271 (3) | 0.62895 (7) | 0.0241 (4) | |
H18 | 0.618881 | 0.830511 | 0.657840 | 0.029* | |
C6 | 0.64079 (6) | 0.3964 (3) | 0.85109 (7) | 0.0230 (4) | |
H6 | 0.632173 | 0.297150 | 0.879814 | 0.028* | |
C24 | 0.71917 (6) | 0.5018 (3) | 0.84579 (7) | 0.0247 (4) | |
C23 | 0.75536 (6) | 0.6403 (3) | 0.86477 (7) | 0.0259 (4) | |
C10 | 0.50940 (6) | −0.1886 (3) | 0.89086 (8) | 0.0273 (4) | |
H10 | 0.493552 | −0.282816 | 0.914192 | 0.033* | |
C11 | 0.52397 (6) | 0.0264 (3) | 0.90983 (7) | 0.0257 (4) | |
H11 | 0.518138 | 0.079165 | 0.946387 | 0.031* | |
C16 | 0.58769 (6) | 0.6439 (3) | 0.52940 (7) | 0.0279 (4) | |
H16 | 0.586508 | 0.687795 | 0.490425 | 0.033* | |
C21 | 0.71147 (6) | 0.8557 (3) | 0.92605 (7) | 0.0241 (4) | |
C9 | 0.51823 (6) | −0.2643 (3) | 0.83749 (8) | 0.0263 (4) | |
H9 | 0.507883 | −0.409838 | 0.823913 | 0.032* | |
C22 | 0.75145 (6) | 0.8155 (3) | 0.90470 (7) | 0.0258 (4) | |
C15 | 0.57181 (6) | 0.4318 (3) | 0.54404 (7) | 0.0273 (4) | |
H15 | 0.559312 | 0.331309 | 0.515037 | 0.033* | |
C25 | 0.63232 (6) | 0.7587 (3) | 0.93028 (8) | 0.0274 (4) | |
H25A | 0.634909 | 0.720712 | 0.971033 | 0.041* | |
H25B | 0.610176 | 0.660797 | 0.909650 | 0.041* | |
H25C | 0.623921 | 0.920034 | 0.925004 | 0.041* | |
C17 | 0.60526 (6) | 0.7913 (3) | 0.57185 (7) | 0.0262 (4) | |
H17 | 0.615984 | 0.936980 | 0.561929 | 0.031* | |
C29 | 0.72431 (6) | 0.3065 (4) | 0.80483 (8) | 0.0315 (5) | |
H29A | 0.697383 | 0.217050 | 0.799632 | 0.047* | |
H29B | 0.748259 | 0.207275 | 0.820370 | 0.047* | |
H29C | 0.730603 | 0.368437 | 0.767938 | 0.047* | |
C26 | 0.70788 (6) | 1.0445 (3) | 0.96918 (8) | 0.0323 (5) | |
H26A | 0.728286 | 1.014941 | 1.003141 | 0.048* | |
H26B | 0.678224 | 1.049016 | 0.979974 | 0.048* | |
H26C | 0.714808 | 1.192160 | 0.952417 | 0.048* | |
C28 | 0.79882 (6) | 0.5958 (4) | 0.84287 (8) | 0.0361 (5) | |
H28A | 0.810760 | 0.740673 | 0.830322 | 0.054* | |
H28B | 0.794943 | 0.488770 | 0.810634 | 0.054* | |
H28C | 0.818874 | 0.529184 | 0.873492 | 0.054* | |
C27 | 0.79006 (6) | 0.9625 (4) | 0.92679 (8) | 0.0353 (5) | |
H27A | 0.796079 | 0.942774 | 0.968195 | 0.053* | |
H27B | 0.783513 | 1.124120 | 0.918115 | 0.053* | |
H27C | 0.815519 | 0.915727 | 0.908311 | 0.053* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C13 | 0.0167 (8) | 0.0278 (10) | 0.0198 (8) | 0.0020 (7) | 0.0020 (7) | 0.0000 (7) |
C7 | 0.0150 (8) | 0.0271 (9) | 0.0210 (8) | −0.0010 (7) | −0.0020 (7) | 0.0029 (7) |
C19 | 0.0204 (9) | 0.0265 (9) | 0.0164 (8) | −0.0024 (7) | −0.0016 (7) | 0.0039 (7) |
C5 | 0.0197 (9) | 0.0242 (9) | 0.0222 (9) | −0.0013 (7) | 0.0009 (7) | −0.0007 (7) |
C20 | 0.0216 (9) | 0.0257 (9) | 0.0182 (8) | −0.0012 (7) | −0.0015 (7) | 0.0046 (7) |
C4 | 0.0203 (9) | 0.0263 (9) | 0.0215 (9) | −0.0013 (7) | 0.0019 (7) | 0.0020 (7) |
C14 | 0.0212 (9) | 0.0273 (10) | 0.0242 (9) | 0.0018 (7) | 0.0027 (7) | −0.0006 (7) |
C12 | 0.0196 (9) | 0.0258 (9) | 0.0224 (9) | −0.0016 (7) | −0.0022 (7) | 0.0006 (7) |
C8 | 0.0198 (9) | 0.0264 (10) | 0.0232 (9) | 0.0009 (7) | −0.0003 (7) | 0.0012 (7) |
C3 | 0.0205 (9) | 0.0229 (9) | 0.0216 (9) | 0.0015 (7) | 0.0033 (7) | 0.0004 (7) |
C1 | 0.0205 (9) | 0.0250 (9) | 0.0208 (9) | −0.0005 (7) | 0.0009 (7) | 0.0000 (7) |
C2 | 0.0190 (9) | 0.0258 (9) | 0.0210 (8) | −0.0018 (7) | 0.0000 (7) | −0.0019 (7) |
C18 | 0.0225 (9) | 0.0275 (10) | 0.0219 (9) | 0.0007 (8) | 0.0011 (7) | −0.0005 (7) |
C6 | 0.0228 (9) | 0.0257 (9) | 0.0204 (8) | −0.0028 (7) | 0.0018 (7) | 0.0021 (7) |
C24 | 0.0240 (9) | 0.0301 (10) | 0.0191 (8) | 0.0002 (8) | −0.0016 (7) | 0.0044 (7) |
C23 | 0.0197 (9) | 0.0344 (11) | 0.0231 (9) | −0.0015 (8) | −0.0004 (7) | 0.0067 (8) |
C10 | 0.0195 (9) | 0.0336 (11) | 0.0283 (10) | −0.0031 (8) | 0.0002 (7) | 0.0079 (8) |
C11 | 0.0204 (9) | 0.0350 (11) | 0.0217 (9) | 0.0010 (8) | 0.0015 (7) | 0.0013 (8) |
C16 | 0.0276 (10) | 0.0373 (11) | 0.0190 (9) | 0.0081 (8) | 0.0035 (7) | 0.0040 (8) |
C21 | 0.0245 (9) | 0.0261 (10) | 0.0206 (8) | −0.0023 (8) | −0.0025 (7) | 0.0043 (7) |
C9 | 0.0227 (9) | 0.0238 (10) | 0.0312 (10) | −0.0034 (7) | −0.0033 (8) | 0.0028 (8) |
C22 | 0.0207 (9) | 0.0316 (10) | 0.0238 (9) | −0.0042 (8) | −0.0037 (7) | 0.0069 (8) |
C15 | 0.0245 (9) | 0.0362 (11) | 0.0208 (9) | 0.0040 (8) | 0.0001 (7) | −0.0049 (8) |
C25 | 0.0211 (9) | 0.0343 (11) | 0.0265 (9) | −0.0006 (8) | 0.0012 (7) | 0.0012 (8) |
C17 | 0.0234 (9) | 0.0300 (10) | 0.0255 (9) | 0.0028 (8) | 0.0047 (7) | 0.0049 (8) |
C29 | 0.0275 (10) | 0.0393 (12) | 0.0274 (10) | 0.0010 (9) | 0.0016 (8) | −0.0027 (8) |
C26 | 0.0303 (10) | 0.0333 (11) | 0.0321 (10) | −0.0053 (9) | −0.0025 (8) | −0.0029 (8) |
C28 | 0.0234 (10) | 0.0534 (14) | 0.0315 (10) | 0.0003 (9) | 0.0026 (8) | 0.0057 (10) |
C27 | 0.0271 (10) | 0.0425 (12) | 0.0350 (11) | −0.0111 (9) | −0.0025 (8) | 0.0037 (9) |
Geometric parameters (Å, º) top C13—C14 | 1.397 (2) | C23—C22 | 1.402 (3) |
C13—C3 | 1.473 (2) | C23—C28 | 1.516 (3) |
C13—C18 | 1.397 (3) | C10—H10 | 0.9500 |
C7—C12 | 1.405 (2) | C10—C11 | 1.389 (3) |
C7—C8 | 1.396 (3) | C10—C9 | 1.387 (3) |
C7—C1 | 1.475 (2) | C11—H11 | 0.9500 |
C19—C20 | 1.409 (2) | C16—H16 | 0.9500 |
C19—C6 | 1.487 (2) | C16—C15 | 1.388 (3) |
C19—C24 | 1.404 (2) | C16—C17 | 1.384 (3) |
C5—C4 | 1.457 (2) | C21—C22 | 1.406 (3) |
C5—C1 | 1.490 (2) | C21—C26 | 1.510 (3) |
C5—C6 | 1.346 (2) | C9—H9 | 0.9500 |
C20—C21 | 1.403 (2) | C22—C27 | 1.517 (3) |
C20—C25 | 1.509 (2) | C15—H15 | 0.9500 |
C4—H4 | 0.9500 | C25—H25A | 0.9800 |
C4—C3 | 1.363 (2) | C25—H25B | 0.9800 |
C14—H14 | 0.9500 | C25—H25C | 0.9800 |
C14—C15 | 1.391 (2) | C17—H17 | 0.9500 |
C12—H12 | 0.9500 | C29—H29A | 0.9800 |
C12—C11 | 1.390 (2) | C29—H29B | 0.9800 |
C8—H8 | 0.9500 | C29—H29C | 0.9800 |
C8—C9 | 1.386 (2) | C26—H26A | 0.9800 |
C3—C2 | 1.472 (2) | C26—H26B | 0.9800 |
C1—C2 | 1.352 (2) | C26—H26C | 0.9800 |
C2—H2 | 0.9500 | C28—H28A | 0.9800 |
C18—H18 | 0.9500 | C28—H28B | 0.9800 |
C18—C17 | 1.391 (2) | C28—H28C | 0.9800 |
C6—H6 | 0.9500 | C27—H27A | 0.9800 |
C24—C23 | 1.415 (3) | C27—H27B | 0.9800 |
C24—C29 | 1.511 (3) | C27—H27C | 0.9800 |
| | | |
C14—C13—C3 | 120.24 (16) | C12—C11—H11 | 119.8 |
C14—C13—C18 | 118.70 (16) | C10—C11—C12 | 120.48 (17) |
C18—C13—C3 | 121.06 (16) | C10—C11—H11 | 119.8 |
C12—C7—C1 | 121.66 (16) | C15—C16—H16 | 120.1 |
C8—C7—C12 | 118.08 (16) | C17—C16—H16 | 120.1 |
C8—C7—C1 | 120.18 (16) | C17—C16—C15 | 119.70 (17) |
C20—C19—C6 | 117.68 (15) | C20—C21—C22 | 119.81 (17) |
C24—C19—C20 | 120.83 (16) | C20—C21—C26 | 120.60 (16) |
C24—C19—C6 | 121.39 (16) | C22—C21—C26 | 119.59 (16) |
C4—C5—C1 | 106.01 (14) | C8—C9—C10 | 120.46 (17) |
C6—C5—C4 | 127.44 (16) | C8—C9—H9 | 119.8 |
C6—C5—C1 | 126.35 (16) | C10—C9—H9 | 119.8 |
C19—C20—C25 | 119.69 (16) | C23—C22—C21 | 120.30 (16) |
C21—C20—C19 | 119.79 (16) | C23—C22—C27 | 121.28 (17) |
C21—C20—C25 | 120.52 (16) | C21—C22—C27 | 118.42 (17) |
C5—C4—H4 | 125.6 | C14—C15—H15 | 119.9 |
C3—C4—C5 | 108.87 (16) | C16—C15—C14 | 120.25 (17) |
C3—C4—H4 | 125.6 | C16—C15—H15 | 119.9 |
C13—C14—H14 | 119.8 | C20—C25—H25A | 109.5 |
C15—C14—C13 | 120.50 (18) | C20—C25—H25B | 109.5 |
C15—C14—H14 | 119.8 | C20—C25—H25C | 109.5 |
C7—C12—H12 | 119.7 | H25A—C25—H25B | 109.5 |
C11—C12—C7 | 120.59 (17) | H25A—C25—H25C | 109.5 |
C11—C12—H12 | 119.7 | H25B—C25—H25C | 109.5 |
C7—C8—H8 | 119.5 | C18—C17—H17 | 119.8 |
C9—C8—C7 | 121.08 (17) | C16—C17—C18 | 120.32 (18) |
C9—C8—H8 | 119.5 | C16—C17—H17 | 119.8 |
C4—C3—C13 | 127.69 (16) | C24—C29—H29A | 109.5 |
C4—C3—C2 | 107.95 (15) | C24—C29—H29B | 109.5 |
C2—C3—C13 | 124.37 (15) | C24—C29—H29C | 109.5 |
C7—C1—C5 | 127.02 (15) | H29A—C29—H29B | 109.5 |
C2—C1—C7 | 125.79 (16) | H29A—C29—H29C | 109.5 |
C2—C1—C5 | 107.15 (15) | H29B—C29—H29C | 109.5 |
C3—C2—H2 | 125.0 | C21—C26—H26A | 109.5 |
C1—C2—C3 | 109.98 (15) | C21—C26—H26B | 109.5 |
C1—C2—H2 | 125.0 | C21—C26—H26C | 109.5 |
C13—C18—H18 | 119.8 | H26A—C26—H26B | 109.5 |
C17—C18—C13 | 120.49 (17) | H26A—C26—H26C | 109.5 |
C17—C18—H18 | 119.8 | H26B—C26—H26C | 109.5 |
C19—C6—H6 | 116.7 | C23—C28—H28A | 109.5 |
C5—C6—C19 | 126.66 (16) | C23—C28—H28B | 109.5 |
C5—C6—H6 | 116.7 | C23—C28—H28C | 109.5 |
C19—C24—C23 | 118.97 (17) | H28A—C28—H28B | 109.5 |
C19—C24—C29 | 121.18 (16) | H28A—C28—H28C | 109.5 |
C23—C24—C29 | 119.81 (16) | H28B—C28—H28C | 109.5 |
C24—C23—C28 | 119.87 (17) | C22—C27—H27A | 109.5 |
C22—C23—C24 | 120.31 (17) | C22—C27—H27B | 109.5 |
C22—C23—C28 | 119.81 (17) | C22—C27—H27C | 109.5 |
C11—C10—H10 | 120.4 | H27A—C27—H27B | 109.5 |
C9—C10—H10 | 120.4 | H27A—C27—H27C | 109.5 |
C9—C10—C11 | 119.27 (17) | H27B—C27—H27C | 109.5 |
| | | |
C13—C14—C15—C16 | −0.1 (3) | C3—C13—C18—C17 | 177.71 (16) |
C13—C3—C2—C1 | −179.76 (16) | C1—C7—C12—C11 | 176.90 (16) |
C13—C18—C17—C16 | 1.2 (3) | C1—C7—C8—C9 | −175.49 (16) |
C7—C12—C11—C10 | −0.8 (3) | C1—C5—C4—C3 | −1.99 (19) |
C7—C8—C9—C10 | −2.1 (3) | C1—C5—C6—C19 | 178.18 (17) |
C7—C1—C2—C3 | 175.98 (16) | C18—C13—C14—C15 | 1.7 (3) |
C19—C20—C21—C22 | −0.3 (2) | C18—C13—C3—C4 | −25.0 (3) |
C19—C20—C21—C26 | −179.85 (16) | C18—C13—C3—C2 | 155.29 (17) |
C19—C24—C23—C22 | 0.4 (3) | C6—C19—C20—C21 | 176.97 (15) |
C19—C24—C23—C28 | 179.05 (16) | C6—C19—C20—C25 | −2.7 (2) |
C5—C4—C3—C13 | −178.73 (16) | C6—C19—C24—C23 | −176.92 (16) |
C5—C4—C3—C2 | 1.0 (2) | C6—C19—C24—C29 | 0.7 (3) |
C5—C1—C2—C3 | −1.7 (2) | C6—C5—C4—C3 | 173.08 (18) |
C20—C19—C6—C5 | 112.0 (2) | C6—C5—C1—C7 | 9.5 (3) |
C20—C19—C24—C23 | −0.5 (3) | C6—C5—C1—C2 | −172.87 (18) |
C20—C19—C24—C29 | 177.06 (16) | C24—C19—C20—C21 | 0.4 (2) |
C20—C21—C22—C23 | 0.2 (3) | C24—C19—C20—C25 | −179.27 (16) |
C20—C21—C22—C27 | −178.62 (16) | C24—C19—C6—C5 | −71.5 (3) |
C4—C5—C1—C7 | −175.40 (16) | C24—C23—C22—C21 | −0.3 (3) |
C4—C5—C1—C2 | 2.27 (19) | C24—C23—C22—C27 | 178.50 (16) |
C4—C5—C6—C19 | 4.1 (3) | C11—C10—C9—C8 | 1.2 (3) |
C4—C3—C2—C1 | 0.5 (2) | C9—C10—C11—C12 | 0.2 (3) |
C14—C13—C3—C4 | 154.94 (18) | C15—C16—C17—C18 | 0.4 (3) |
C14—C13—C3—C2 | −24.7 (3) | C25—C20—C21—C22 | 179.43 (16) |
C14—C13—C18—C17 | −2.3 (3) | C25—C20—C21—C26 | −0.1 (2) |
C12—C7—C8—C9 | 1.5 (2) | C17—C16—C15—C14 | −1.0 (3) |
C12—C7—C1—C5 | 42.2 (3) | C29—C24—C23—C22 | −177.17 (16) |
C12—C7—C1—C2 | −135.07 (19) | C29—C24—C23—C28 | 1.4 (3) |
C8—C7—C12—C11 | 0.0 (2) | C26—C21—C22—C23 | 179.79 (16) |
C8—C7—C1—C5 | −140.94 (18) | C26—C21—C22—C27 | 1.0 (2) |
C8—C7—C1—C2 | 41.8 (3) | C28—C23—C22—C21 | −178.90 (16) |
C3—C13—C14—C15 | −178.30 (16) | C28—C23—C22—C27 | −0.1 (3) |
Hydrogen-bond geometry (Å, º) topCg10 is the centroid of the C13–C18 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···Cg10i | 0.95 | 2.70 | 3.4521 (9) | 136 |
Symmetry code: (i) −x, y+1, −z+1/2. |
Fulvene-phenyl torsion angles (°) top | I | II | III | IV |
Fulvenea-(1-phenylb) | 32.08 (7) | 31.83 (5) | 21.33 (13) | 41.65 (7) |
Fulvenea-(3-phenylb) | 19.50 (6) | 20.92 (5) | 38.02 (13) | 25.17 (7) |
Fulvenea-(6-phenylb) | 31.99 (6) | 35.13 (5) | 57.22 (14) | 64.15 (7) |
Notes: (a) plane defined by atoms C1–C5; (a) plane defined by the atoms of the specific phenyl ring substituent. |
Funding information
Funding for this research was provided by: Air Force Office of Scientific Research.
References
Adas, S. K. & Balaich, G. J. (2018). J. Organomet. Chem. 857, 200–206. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2017). APEX3 and SAINT. Bruker–Nonius AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E. & Orpen, A. G. (2004). J. Chem. Inf. Comput. Sci. 44, 2133–2144. Web of Science CrossRef PubMed CAS Google Scholar
Erker, G. (2011). Organometallics, 30, 358–368. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gómez-Ruiz, S., Höcher, T., Prashar, S. & Hey-Hawkins, E. (2005). Organometallics, 24, 2061–2064. Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Jayamurugan, G., Dumele, O., Gisselbrecht, J. P., Boudon, C., Schweizer, W. B., Bernet, B. & Diederich, F. (2013). J. Am. Chem. Soc. 135, 3599–3606. CSD CrossRef CAS PubMed Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mömming, C. M., Kehr, G., Fröhlich, R. & Erker, G. (2011). Chem. Commun. 47, 2006–2007. Google Scholar
Peloquin, A. J., Stone, R. L., Avila, S. E., Rudico, E. R., Horn, C. B., Gardner, K. A., Ball, D. W., Johnson, J. E. B., Iacono, S. T. & Balaich, G. J. (2012). J. Org. Chem. 77, 6371–6376. Web of Science CSD CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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