#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/08/4020816.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_4020816
loop_
_publ_author_name
'Yu-Shiang Lin'
'Shi-Yi Chang'
'Ming-Shyong Yang'
'Chitneni Prasad Rao'
'Rama Krishna Peddinti'
'Yow-Fu Tsai'
'Chun-Chen Liao'
_publ_section_title
;
 Diels-Alder Reactions of
 4-Triflyloxy-2,6,6-trimethyl-2,4-cyclohexadienone.
 An Expedient Methodology for the Synthesis of
 Bicyclo[2.2.2]oct-5-en-2-ones and
 Bicyclo[2.2.2]octa-5,7-dien-2-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              447
_journal_page_last               458
_journal_paper_doi               10.1021/jo035429y
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C18 H19 F3 O4 S'
_chemical_formula_weight         388.39
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 109.82(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.517(4)
_cell_length_b                   7.416(2)
_cell_length_c                   24.716(5)
_cell_measurement_temperature    295(2)
_cell_volume                     3710.4(13)
_diffrn_ambient_temperature      295(2)
_exptl_crystal_density_diffrn    1.391
_refine_ls_R_factor_obs          0.0837
_refine_ls_wR_factor_obs         0.2795
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4020816
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
S1 S 0.33966(6) 0.0237(2) 0.22580(5) 0.0855(5) Uani 1 d . .
O1 O 0.47926(14) 0.6086(3) 0.41777(13) 0.0694(8) Uani 1 d . .
O2 O 0.40141(15) 0.1318(5) 0.26239(12) 0.0773(9) Uani 1 d . .
O3 O 0.2890(2) 0.0211(9) 0.2500(2) 0.154(2) Uani 1 d . .
O4 O 0.3302(4) 0.0603(8) 0.1681(2) 0.166(2) Uani 1 d . .
C1 C 0.39865(15) 0.3696(4) 0.39444(13) 0.0443(7) Uani 1 d . .
C2 C 0.4647(2) 0.4561(4) 0.39991(13) 0.0455(7) Uani 1 d . .
C3 C 0.5130(2) 0.3355(5) 0.38342(14) 0.0507(8) Uani 1 d . .
C4 C 0.4768(2) 0.1523(5) 0.3646(2) 0.0508(8) Uani 1 d . .
H4A H 0.5029(2) 0.0693(5) 0.3501(2) 0.061 Uiso 1 calc R .
C5 C 0.4124(2) 0.1971(5) 0.31950(13) 0.0520(8) Uani 1 d . .
C6 C 0.3712(2) 0.3034(5) 0.33317(14) 0.0497(8) Uani 1 d . .
H6A H 0.3297(2) 0.3345(5) 0.30784(14) 0.060 Uiso 1 calc R .
C7 C 0.42056(15) 0.2060(4) 0.43789(13) 0.0440(7) Uani 1 d . .
H7A H 0.45175(15) 0.2540(4) 0.47379(13) 0.053 Uiso 1 calc R .
C8 C 0.4590(2) 0.0683(5) 0.4143(2) 0.0526(8) Uani 1 d . .
H8A H 0.4991(2) 0.0323(5) 0.4447(2) 0.063 Uiso 1 calc R .
H8B H 0.4322(2) -0.0385(5) 0.4007(2) 0.063 Uiso 1 calc R .
C9 C 0.3520(2) 0.4995(5) 0.4092(2) 0.0615(9) Uani 1 d . .
H9A H 0.3714(2) 0.5378(5) 0.4484(2) 0.092 Uiso 1 calc R .
H9B H 0.3108(2) 0.4400(5) 0.4042(2) 0.092 Uiso 1 calc R .
H9C H 0.3444(2) 0.6025(5) 0.3843(2) 0.092 Uiso 1 calc R .
C10 C 0.5301(2) 0.4248(6) 0.3341(2) 0.0714(11) Uani 1 d . .
H10A H 0.5604(2) 0.3496(6) 0.3236(2) 0.107 Uiso 1 calc R .
H10B H 0.5500(2) 0.5402(6) 0.3465(2) 0.107 Uiso 1 calc R .
H10C H 0.4905(2) 0.4403(6) 0.3016(2) 0.107 Uiso 1 calc R .
C11 C 0.5765(2) 0.3128(7) 0.4356(2) 0.0758(12) Uani 1 d . .
H11A H 0.6069(2) 0.2370(7) 0.4253(2) 0.114 Uiso 1 calc R .
H11B H 0.5660(2) 0.2585(7) 0.4667(2) 0.114 Uiso 1 calc R .
H11C H 0.5963(2) 0.4288(7) 0.4474(2) 0.114 Uiso 1 calc R .
C12 C 0.3772(5) -0.2011(12) 0.2401(4) 0.141(3) Uani 1 d . .
C13 C 0.3637(2) 0.1237(4) 0.4524(2) 0.0497(8) Uani 1 d . .
C14 C 0.3606(2) 0.1493(5) 0.5075(2) 0.0574(9) Uani 1 d . .
H14A H 0.3937(2) 0.2146(5) 0.5345(2) 0.069 Uiso 1 calc R .
C15 C 0.3095(2) 0.0795(6) 0.5224(2) 0.0718(11) Uani 1 d . .
H15A H 0.3077(2) 0.1000(6) 0.5589(2) 0.086 Uiso 1 calc R .
C16 C 0.2614(2) -0.0199(6) 0.4834(3) 0.0807(14) Uani 1 d . .
H16A H 0.2271(2) -0.0679(6) 0.4937(3) 0.097 Uiso 1 calc R .
C17 C 0.2635(2) -0.0490(7) 0.4298(3) 0.0823(14) Uani 1 d . .
H17A H 0.2302(2) -0.1154(7) 0.4034(3) 0.099 Uiso 1 calc R .
C18 C 0.3159(2) 0.0214(6) 0.4142(2) 0.0741(12) Uani 1 d . .
H18A H 0.3179(2) -0.0018(6) 0.3779(2) 0.089 Uiso 1 calc R .
F1 F 0.3908(5) -0.2313(7) 0.2938(3) 0.247(4) Uani 1 d . .
F2 F 0.3281(3) -0.3134(7) 0.2077(3) 0.212(3) Uani 1 d . .
F3 F 0.4230(3) -0.2040(10) 0.2196(4) 0.259(4) Uani 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
S1 O4 1.396(5) . ?
S1 O3 1.410(5) . ?
S1 O2 1.553(3) . ?
S1 C12 1.834(9) . ?
O1 C2 1.216(4) . ?
O2 C5 1.434(4) . ?
C1 C6 1.509(4) . ?
C1 C9 1.522(5) . ?
C1 C2 1.524(5) . ?
C1 C7 1.582(4) . ?
C2 C3 1.527(5) . ?
C3 C10 1.537(5) . ?
C3 C11 1.537(5) . ?
C3 C4 1.556(5) . ?
C4 C5 1.492(5) . ?
C4 C8 1.535(5) . ?
C5 C6 1.313(5) . ?
C7 C13 1.517(4) . ?
C7 C8 1.549(5) . ?
C12 F3 1.253(10) . ?
C12 F1 1.278(9) . ?
C12 F2 1.371(10) . ?
C13 C18 1.366(6) . ?
C13 C14 1.396(5) . ?
C14 C15 1.374(6) . ?
C15 C16 1.366(7) . ?
C16 C17 1.358(7) . ?
C17 C18 1.410(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139089602
