Ethyl 5-hydroxy-6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate

被引:0
作者
McAdam, C. John [1 ]
Moratti, Stephen C. [1 ]
Simpson, Jim [1 ]
Shi, Zheng [1 ]
机构
[1] Univ Otago, Dept Chem, Dunedin, New Zealand
来源
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE | 2011年 / 67卷
关键词
data-to-parameter ratio = 13.3; mean σ(C-C) = 0.002 Å; R factor =0.032; single-crystal X-ray study; T = 91 K; wR factor = 0.079;
D O I
10.1107/S1600536811037032
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
In the title molecule, C16H14O4S, the dihydrocyclopentathiophenone ring system is almost planar, with an r.m.s. deviation of 0.060 angstrom from the best fit plane through all nine non-H atoms. The cyclopentanone ring adopts a severely flattened envelope conformation with the C atom carrying the OH and ethylcarboxylate substituents at the flap. This atom lies only 0.185 (3) angstrom from the plane through the other four C atoms. The phenyl substituent is inclined at 43.37 (5)degrees to the dihydrocyclopentathiophenone mean plane. In the crystal, molecules are linked by pairs of O-H center dot center dot center dot O hydrogen bonds, forming inversion dimers with R-2(2)(10) ring motifs. Weak C-H center dot center dot center dot O hydrogen bonds also link molecules into chains along c, while an approximately orthogonal set of C-H center dot center dot center dot O contacts form chains along b, resulting in layers lying parallel to (100). Inversion dimers also form through weaker R-2(2)(12) C-H center dot center dot center dot S contacts, which combine with C-H center dot center dot center dot O contacts to form stacks along b.
引用
收藏
页码:O2764 / +
页数:13
相关论文
共 14 条
  • [1] TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS
    ALLEN, FH
    KENNARD, O
    WATSON, DG
    BRAMMER, L
    ORPEN, AG
    TAYLOR, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12): : S1 - S19
  • [2] CIF applications. XV. enCIFer: a program for viewing, editing and visualizing CIFs
    Allen, FH
    Johnson, O
    Shields, GP
    Smith, BR
    Towler, M
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2004, 37 : 335 - 338
  • [3] The Cambridge Structural Database: a quarter of a million crystal structures and rising
    Allen, FH
    [J]. ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2002, 58 (3 PART 1): : 380 - 388
  • [4] Recent advances in thiophene based molecular actuators
    Anquetil, PA
    Yu, HH
    Madden, JD
    Swager, TM
    Hunter, IW
    [J]. SMART STRUCTURES AND MATERIALS 2003: ELECTROACTIVE POLYMER ACTUATORS AND DEVICES (EAPAD), 2003, 5051 : 42 - 53
  • [5] PATTERNS IN HYDROGEN BONDING - FUNCTIONALITY AND GRAPH SET ANALYSIS IN CRYSTALS
    BERNSTEIN, J
    DAVIS, RE
    SHIMONI, L
    CHANG, NL
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (15) : 1555 - 1573
  • [6] Diastereoselective synthesis of thieno[3′,2′:4,5]cyclopenta[1,2-d][1,3]-oxazolines -: New ligands for the copper-catalyzed asymmetric conjugate addition of diethylzinc to enones
    Bonini, BF
    Capitò, E
    Comes-Franchini, M
    Ricci, A
    Bottoni, A
    Bernardi, F
    Miscione, GP
    Giordano, L
    Cowley, AR
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (21) : 4442 - 4451
  • [7] Bruker, 2011, APEX2 SAINT SADABS
  • [8] Cobalt-catalyzed regioselective carbocyclization reaction of o-iodophenyl ketones and aldehydes with alkynes, acrylates, and acrylonitrile:: A facile route to indenols and indenes
    Chang, KJ
    Rayabarapu, DK
    Cheng, CH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (14) : 4781 - 4787
  • [9] Hunter K. A., 1999, TITAN2000
  • [10] Mercury CSD 2.0 -: new features for the visualization and investigation of crystal structures
    Macrae, Clare F.
    Bruno, Ian J.
    Chisholm, James A.
    Edgington, Paul R.
    McCabe, Patrick
    Pidcock, Elna
    Rodriguez-Monge, Lucia
    Taylor, Robin
    van de Streek, Jacco
    Wood, Peter A.
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2008, 41 : 466 - 470