Crystal structure of 5,6-diphenyldibenzo[c, g]chrysene, C38H24

Zhang Bin; Chen Xin; Chen Songhua

doi:10.1515/ncrs-2020-0112

Open Access Published by De Gruyter (O) June 2, 2020

Crystal structure of 5,6-diphenyldibenzo[c, g]chrysene, C₃₈H₂₄

Zhang Bin , Chen Xin and Chen Songhua

From the journal Zeitschrift für Kristallographie - New Crystal Structures

https://doi.org/10.1515/ncrs-2020-0112

Abstract

C₃₈H₂₄, monoclinic, C2/c (no. 15), a = 37.6829(14) Å, b = 7.4695(3) Å, c = 17.4881(7) Å, β = 95.269(3)°, V = 4901.6(3) Å³, Z = 8, R_gt(F) = 0.0472, wR_ref(F²) = 0.1177, T = 123(2) K.

CCDC no.: 1977274

The molecular structure is shown in the figure (hydrogen atoms are olitted for clarity). Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:	Colourless block
Size:	0.20 × 0.05 × 0.01 mm
Wavelength:	Mo Kα radiation (0.71073 Å)
μ:	0.07 mm⁻¹
Diffractometer, scan mode:	Rigaku IP, ω
θ_max, completeness:	30.7°, >99%
N(hkl)_measured, N(hkl)_unique, R_int:	33046, 6962, 0.043
Criterion for I_obs, N(hkl)_gt:	I_obs > 2 σ(I_obs), 5151
N(param)_refined:	343
Programs:	Olex2 [1], SHELX [2], [3]

Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²).

Atom	x	y	z	U_iso*/U_eq
C1	0.62538(3)	0.72504(16)	0.32524(6)	0.0240(3)
C2	0.63409(4)	0.81998(17)	0.25881(7)	0.0283(3)
C3	0.66710(4)	0.78792(18)	0.22985(7)	0.0313(3)
H3	0.673974	0.858193	0.188401	0.038*
C4	0.68945(4)	0.65686(18)	0.26054(7)	0.0302(3)
H4	0.712431	0.643370	0.243015	0.036*
C5	0.67866(3)	0.54153(17)	0.31803(6)	0.0247(3)
C6	0.64643(3)	0.57193(16)	0.34946(6)	0.0221(2)
C7	0.70289(3)	0.38998(17)	0.34326(7)	0.0255(3)
C8	0.73725(3)	0.42797(19)	0.37610(8)	0.0320(3)
H8	0.745041	0.548865	0.379912	0.038*
C9	0.76016(4)	0.2927(2)	0.40318(9)	0.0370(3)
H9	0.783276	0.321274	0.426251	0.044*
C10	0.74938(4)	0.1155(2)	0.39665(8)	0.0346(3)
H10	0.764950	0.022346	0.415589	0.042*
C11	0.71573(4)	0.07527(19)	0.36230(7)	0.0326(3)
H11	0.708480	−0.046182	0.356655	0.039*
C12	0.69253(4)	0.21071(18)	0.33606(7)	0.0290(3)
H12	0.669449	0.181359	0.313037	0.035*
C13	0.63260(3)	0.43937(15)	0.40349(6)	0.0210(2)
C14	0.65229(3)	0.38557(16)	0.47124(7)	0.0237(2)
H14	0.675835	0.429240	0.483000	0.028*
C15	0.63765(4)	0.26886(17)	0.52136(7)	0.0286(3)
H15	0.651134	0.234599	0.567614	0.034*
C16	0.60364(4)	0.20186(17)	0.50474(8)	0.0310(3)
H16	0.593545	0.124177	0.539909	0.037*
C17	0.58439(4)	0.24876(17)	0.43651(8)	0.0289(3)
H17	0.561282	0.200245	0.423971	0.035*
C18	0.59878(3)	0.36650(16)	0.38637(7)	0.0246(3)
H18	0.585364	0.397936	0.339643	0.030*
C19	0.60849(4)	0.93961(18)	0.22071(7)	0.0336(3)
H19	0.614714	1.007106	0.177886	0.040*
C20	0.57573(4)	0.95769(18)	0.24476(7)	0.0344(3)
H20	0.557904	1.021831	0.214064	0.041*
C21	0.56744(3)	0.88080(17)	0.31650(7)	0.0282(3)
C22	0.59435(3)	0.78679(16)	0.36203(7)	0.0238(3)
C23	0.58924(3)	0.76135(15)	0.44195(7)	0.0212(2)
C24	0.55469(3)	0.76778(16)	0.46551(7)	0.0243(3)
C25	0.52672(3)	0.83955(19)	0.41422(8)	0.0312(3)
H25	0.503032	0.841836	0.428661	0.037*
C26	0.53384(4)	0.90496(19)	0.34448(8)	0.0329(3)
H26	0.515783	0.968174	0.314066	0.039*
C27	0.61918(3)	0.74815(15)	0.50130(6)	0.0205(2)
C28	0.65304(3)	0.81587(16)	0.48923(7)	0.0232(2)
H28	0.656661	0.869082	0.441218	0.028*
C29	0.68106(3)	0.80672(17)	0.54545(7)	0.0265(3)
H29	0.703814	0.851680	0.535877	0.032*
C30	0.67589(3)	0.73103(18)	0.61668(7)	0.0285(3)
H30	0.695387	0.719539	0.654842	0.034*
C31	0.64263(3)	0.67334(17)	0.63143(7)	0.0263(3)
H31	0.639226	0.625546	0.680566	0.032*
C32	0.61331(3)	0.68353(15)	0.57502(6)	0.0215(2)
C33	0.57724(3)	0.64003(16)	0.59234(7)	0.0234(2)
C34	0.54817(3)	0.69705(16)	0.54120(7)	0.0246(3)
C35	0.51341(4)	0.6694(2)	0.56204(8)	0.0334(3)
H35	0.493696	0.710996	0.529060	0.040*
C36	0.50736(4)	0.5834(2)	0.62909(8)	0.0380(3)
H36	0.483674	0.567513	0.642325	0.046*
C37	0.53594(4)	0.5194(2)	0.67772(8)	0.0356(3)
H37	0.531732	0.456455	0.723221	0.043*
C38	0.57024(4)	0.54773(18)	0.65961(7)	0.0297(3)
H38	0.589600	0.504217	0.693109	0.036*

Source of materials

The title compound was obtained by Scholl-based cyclodehydrogenation of 3,4,5,6-tetraphenylphenanthrene with equal ratio FeCl₃ and the compound was purified through flash column chromatography. Single crystals suitable for X-ray diffraction were obtained by crystallization of the title compound from dichloromethane and n-hexane.

Experimental details

The hydrogen atoms were placed with common isotropic displacement factors U_iso(H) = 1.2 times U_eq(C, aromatic ring). The final refinement succeeded using geometrical restraints, with C—H = 0.95 Å.

Comment

Helicene and its derivatives are one of the traditional π-conjugated functional molecules due to their steric demands [4], [5], [6], [7]. They have been widely utilized materials in the science of supramolecular chemistry and asymmetric synthesis [8]. To date, a series of helicenes derivatives were synthesized showing specific physical properties and optical properties, especially the excellent luminescent properties. In this paper, we reported the synthesis of the title compound showing chiral optical property by cyclodehydrogenation of phenylphenanthrene using FeCl₃ as catalyst [9], [10], [11]. A view on the structure of the title molecule is shown in the figure.

Acknowledgements

This work was funded by the research funds of Youth Talented Scholars Plan in Universities of Fujian Province, Young and Middle-aged Teacher in Science Research of Fujian Province (No. JAT190732) and Science and Technology Program of Longyan (No. LY2018LYF8007).

References

1. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H.: OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 42 (2009) 339–341.10.1107/S0021889808042726Search in Google Scholar

2. Sheldrick, G. M.: Crystal structure refinement with SHELX. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central

3. Sheldrick, G. M.: Crystal structure refinement with SHELX. Acta Crystallogr. A71 (2015) 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central

4. Shen, Y.; Chen, C.-F.: Helicenes: synthesis and applications. Chem. Rev. 112 (2012) 1463–1535.10.1021/cr200087rSearch in Google Scholar PubMed

5. Tinnemans, A. H. A.; Laarhoven, W. H.: Photodehydrocyclizations in stilbene-like compounds. X. rearrangements in the photocyclization of 4,5-diphenyltriphenylene and 4,5-diphenylphenanthrene. J. Am. Chem. Soc. 96 (1974) 4617–4622.10.1021/ja00821a043Search in Google Scholar

6. S. Barlow, S.; Marder, S. R.: Chapter 11: nonlinear optical properties of organic materials. In: Functional organic materials: syntheses, strategies and applications (Eds. Müller, T. J. J.; Bunz, U. H. F.), p. 393–437. Wiley-VCH, Weinheim (2007).10.1002/9783527610266.ch11Search in Google Scholar

7. Ogawa, N.; Yamaoka, Y.; Takikawa, H.; Takasu, K.: Synthesis of polycyclic spirocarbocycles via acid-promoted ring-contraction/dearomative ring-closure cascade of oxapropellanes. Org. Lett. 21 (2019) 7563–7567.10.1021/acs.orglett.9b02835Search in Google Scholar PubMed

8. Sharma, B. K. A.; Shaikh, M.; Agarwal, N.; Kamble, R. M.: Synthesis, photophysical and electrochemical studies of acridone-amine based donor-acceptors for hole transport materials. RSC Adv. 6 (2016) 17129–17137.10.1039/C5RA25115JSearch in Google Scholar

9. Hemgesberg, M.; Ohlmann, D. M.; Schmitt, Y.; Wolfe, M. R.; Müller, M. K.; Erb, B.; Sun, Y.; Gooßen, L. J.; Gerhards, M.; Thiel, W. R.: Simple access to sol–gel precursors bearing fluorescent aromatic core units. Eur. J. Org. Chem. 2012 (2012) 2142–2151.10.1002/ejoc.201200076Search in Google Scholar

10. Chen, S.; Li, Y.; Yang, W.; Chen, N.; Liu, H.; Li, Y.: Synthesis and tuning optical nonlinear properties of molecular crystals of benzothiadiazole. J. Phys. Chem. C 114 (2010) 15109–15115.10.1021/jp103159bSearch in Google Scholar

11. Carreras, J.; Patil, M.; Thiel, W.; Alcarazo, M.: Exploiting the π-acceptor properties of carbene-stabilized phosphorus centered trications [L₃P]³⁺: applications in Pt(II) catalysis. J. Am. Chem. Soc. 134 (2012) 16753–16758.10.1021/ja306947mSearch in Google Scholar PubMed

Received: 2020-02-29

Accepted: 2020-04-06

Published Online: 2020-06-02

Published in Print: 2020-08-26

This work is licensed under the Creative Commons Attribution 4.0 International License.