#------------------------------------------------------------------------------
#$Date: 2015-01-27 21:58:39 +0200 (Tue, 27 Jan 2015) $
#$Revision: 130149 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/10/4021034.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4021034
loop_
_publ_author_name
'James H. Rigby'
'Mundruppady S. Laxmisha'
'Andrew R. Hudson'
'Charles H. Heap'
'Mary Jane Heeg'
_publ_section_title
;
 Chromium(0)-Promoted Multicomponent Cycloaddition
 of Tethered Diynes with Cyclic Trienes:
 Application to the Total Synthesis of 9-epi-Pentalenic Acid
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6751
_journal_page_last               6760
_journal_paper_doi               10.1021/jo040204o
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C16 H20 O'
_chemical_formula_weight         228.32
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                102.617(4)
_cell_angle_beta                 111.877(3)
_cell_angle_gamma                102.583(5)
_cell_formula_units_Z            4
_cell_length_a                   10.6317(19)
_cell_length_b                   11.6413(19)
_cell_length_c                   12.227(2)
_cell_measurement_temperature    295(2)
_cell_volume                     1293.5(4)
_diffrn_ambient_temperature      295(2)
_exptl_crystal_density_diffrn    1.172
_cod_database_code               4021034
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.39428(14) 0.06514(11) 0.10644(11) 0.0544(3) Uani 1 1 d . . .
C1 C 0.39963(17) 0.18697(14) 0.16677(14) 0.0447(3) Uani 1 1 d . . .
C2 C 0.51540(18) 0.24593(16) 0.30542(16) 0.0551(4) Uani 1 1 d . . .
C3 C 0.46861(18) 0.35599(17) 0.35584(18) 0.0548(4) Uani 1 1 d . . .
C4 C 0.30498(16) 0.32093(13) 0.27216(14) 0.0432(3) Uani 1 1 d . . .
C5 C 0.26800(16) 0.19508(13) 0.17953(13) 0.0422(3) Uani 1 1 d . . .
C6 C 0.14369(18) 0.11681(16) 0.15615(16) 0.0516(4) Uani 1 1 d . . .
C7 C 0.06919(19) 0.18309(17) 0.22245(18) 0.0572(4) Uani 1 1 d . . .
C8 C 0.19841(18) 0.29540(15) 0.32885(15) 0.0502(4) Uani 1 1 d . . .
C9 C 0.1704(2) 0.41861(18) 0.3692(2) 0.0609(5) Uani 1 1 d . . .
C10 C 0.2050(2) 0.49213(18) 0.2913(2) 0.0628(5) Uani 1 1 d . . .
C11 C 0.27282(19) 0.42456(15) 0.22120(18) 0.0527(4) Uani 1 1 d . . .
C12 C 0.1204(2) 0.42438(19) 0.1519(2) 0.0640(5) Uani 1 1 d . . .
C13 C -0.0162(2) 0.3215(2) 0.1004(2) 0.0708(6) Uani 1 1 d . . .
C14 C -0.0426(2) 0.2205(2) 0.1317(2) 0.0685(5) Uani 1 1 d . . .
C15 C 0.5064(3) 0.1531(2) 0.3748(2) 0.0815(7) Uani 1 1 d . . .
C16 C 0.6659(2) 0.2891(3) 0.3136(3) 0.0891(9) Uani 1 1 d . . .
O2 O 0.40652(14) 0.05532(12) -0.11768(11) 0.0553(3) Uani 1 1 d . . .
C17 C 0.36023(16) 0.11200(14) -0.21008(14) 0.0430(3) Uani 1 1 d . . .
C18 C 0.47103(17) 0.23676(16) -0.19174(17) 0.0523(4) Uani 1 1 d . . .
C19 C 0.3737(2) 0.2977(2) -0.2725(3) 0.0742(6) Uani 1 1 d . . .
C20 C 0.21982(18) 0.24198(17) -0.28533(19) 0.0564(4) Uani 1 1 d . . .
C21 C 0.23614(15) 0.15222(14) -0.21351(14) 0.0427(3) Uani 1 1 d . . .
C22 C 0.16059(18) 0.15068(19) -0.14895(16) 0.0556(4) Uani 1 1 d . . .
C23 C 0.0720(2) 0.2370(2) -0.1738(3) 0.0760(6) Uani 1 1 d . . .
C24 C 0.1543(3) 0.3251(2) -0.2241(3) 0.0875(8) Uani 1 1 d . . .
C25 C 0.0612(5) 0.3656(5) -0.3333(8) 0.163(3) Uani 1 1 d . . .
C26 C 0.0227(3) 0.2673(5) -0.4555(4) 0.1159(13) Uani 1 1 d . . .
C27 C 0.1099(2) 0.1886(3) -0.4230(2) 0.0828(7) Uani 1 1 d . . .
C28 C -0.0508(3) 0.1442(4) -0.4624(3) 0.1055(11) Uani 1 1 d . . .
C29 C -0.1272(2) 0.1208(3) -0.3871(3) 0.0918(9) Uani 1 1 d . . .
C30 C -0.0811(2) 0.1614(3) -0.2669(3) 0.0810(7) Uani 1 1 d . . .
C31 C 0.5830(3) 0.2119(3) -0.2340(3) 0.0761(6) Uani 1 1 d . . .
C32 C 0.5460(3) 0.3180(3) -0.0540(3) 0.0844(7) Uani 1 1 d . . .
H01 H 0.392(3) 0.068(3) 0.033(3) 0.101(9) Uiso 1 1 d . . .
H1 H 0.423(2) 0.2406(17) 0.1198(17) 0.049(4) Uiso 1 1 d . . .
H3A H 0.495(3) 0.371(2) 0.448(2) 0.080(7) Uiso 1 1 d . . .
H3B H 0.519(3) 0.430(2) 0.345(2) 0.083(7) Uiso 1 1 d . . .
H6 H 0.098(2) 0.028(2) 0.105(2) 0.065(6) Uiso 1 1 d . . .
H7 H 0.029(2) 0.125(2) 0.260(2) 0.065(6) Uiso 1 1 d . . .
H8 H 0.241(2) 0.2650(19) 0.399(2) 0.065(6) Uiso 1 1 d . . .
H9A H 0.076(3) 0.403(2) 0.362(2) 0.074(6) Uiso 1 1 d . . .
H9B H 0.233(3) 0.463(3) 0.460(3) 0.096(8) Uiso 1 1 d . . .
H10 H 0.239(2) 0.586(2) 0.324(2) 0.070(6) Uiso 1 1 d . . .
H11 H 0.344(2) 0.471(2) 0.194(2) 0.067(6) Uiso 1 1 d . . .
H12 H 0.116(3) 0.481(2) 0.099(2) 0.081(7) Uiso 1 1 d . . .
H13 H -0.098(3) 0.337(3) 0.039(3) 0.098(8) Uiso 1 1 d . . .
H14 H -0.133(3) 0.164(3) 0.096(3) 0.103(9) Uiso 1 1 d . . .
H15A H 0.582(3) 0.195(3) 0.462(3) 0.100(8) Uiso 1 1 d . . .
H15B H 0.399(4) 0.121(3) 0.370(3) 0.136(13) Uiso 1 1 d . . .
H15C H 0.532(3) 0.081(3) 0.339(3) 0.112(9) Uiso 1 1 d . . .
H16A H 0.690(3) 0.217(3) 0.277(3) 0.119(10) Uiso 1 1 d . . .
H16B H 0.746(3) 0.327(3) 0.401(3) 0.105(9) Uiso 1 1 d . . .
H16C H 0.665(3) 0.353(3) 0.269(3) 0.091(9) Uiso 1 1 d . . .
H02 H 0.462(3) 0.019(2) -0.129(2) 0.082(7) Uiso 1 1 d . . .
H17 H 0.337(2) 0.0517(17) -0.2918(17) 0.048(4) Uiso 1 1 d . . .
H19A H 0.371(4) 0.271(4) -0.369(4) 0.144(13) Uiso 1 1 d . . .
H19B H 0.419(4) 0.391(3) -0.216(3) 0.120(11) Uiso 1 1 d . . .
H22 H 0.159(2) 0.103(2) -0.092(2) 0.068(6) Uiso 1 1 d . . .
H23 H 0.074(3) 0.281(3) -0.097(3) 0.102(9) Uiso 1 1 d . . .
H24 H 0.228(3) 0.384(3) -0.145(3) 0.105(10) Uiso 1 1 d . . .
H25A H -0.004(5) 0.385(4) -0.307(4) 0.168(16) Uiso 1 1 d . . .
H25B H 0.072(3) 0.383(3) -0.362(2) 0.055(8) Uiso 1 1 d . . .
H26 H 0.004(4) 0.298(3) -0.542(3) 0.129(11) Uiso 1 1 d . . .
H27 H 0.149(4) 0.151(3) -0.490(3) 0.113(10) Uiso 1 1 d . . .
H28 H -0.114(4) 0.101(3) -0.550(4) 0.127(11) Uiso 1 1 d . . .
H29 H -0.220(4) 0.065(3) -0.440(3) 0.107(9) Uiso 1 1 d . . .
H30 H -0.138(3) 0.136(3) -0.234(3) 0.096(8) Uiso 1 1 d . . .
H31A H 0.528(3) 0.163(2) -0.328(3) 0.087(8) Uiso 1 1 d . . .
H31B H 0.655(3) 0.298(3) -0.225(3) 0.105(9) Uiso 1 1 d . . .
H31C H 0.641(3) 0.162(3) -0.184(3) 0.095(8) Uiso 1 1 d . . .
H32A H 0.606(3) 0.262(3) 0.000(3) 0.101(9) Uiso 1 1 d . . .
H32B H 0.611(3) 0.401(3) -0.048(3) 0.107(9) Uiso 1 1 d . . .
H32C H 0.478(4) 0.341(3) -0.015(3) 0.125(11) Uiso 1 1 d . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4266(18) . ?
C1 C5 1.485(2) . ?
C1 C2 1.558(2) . ?
C2 C15 1.521(3) . ?
C2 C16 1.527(3) . ?
C2 C3 1.559(2) . ?
C3 C4 1.556(2) . ?
C4 C5 1.509(2) . ?
C4 C11 1.520(2) . ?
C4 C8 1.543(2) . ?
C5 C6 1.319(2) . ?
C6 C7 1.533(2) . ?
C7 C14 1.513(3) . ?
C7 C8 1.559(2) . ?
C8 C9 1.542(2) . ?
C9 C10 1.503(3) . ?
C10 C11 1.512(2) . ?
C10 C12 1.515(3) . ?
C11 C12 1.522(3) . ?
C12 C13 1.474(3) . ?
C13 C14 1.319(3) . ?
O2 C17 1.4166(18) . ?
C17 C21 1.483(2) . ?
C17 C18 1.569(2) . ?
C18 C31 1.519(3) . ?
C18 C32 1.530(3) . ?
C18 C19 1.554(3) . ?
C19 C20 1.557(2) . ?
C20 C21 1.503(2) . ?
C20 C27 1.532(3) . ?
C20 C24 1.532(3) . ?
C21 C22 1.320(2) . ?
C22 C23 1.523(3) . ?
C23 C30 1.509(4) . ?
C23 C24 1.575(4) . ?
C24 C25 1.574(6) . ?
C25 C26 1.518(8) . ?
C26 C28 1.443(5) . ?
C26 C27 1.454(4) . ?
C27 C28 1.521(3) . ?
C28 C29 1.468(4) . ?
C29 C30 1.296(4) . ?
