#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/04/4020440.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_4020440
loop_
_publ_author_name
'Chisato Mukai'
'Fuyuhiko Inagaki'
'Tatsunori Yoshida'
'Katsuya Yoshitani'
'Yasuyuki Hara'
'Shinji Kitagaki'
_publ_section_title
;
 Rh(I)-Catalyzed Pauson-Khand Reaction and Cycloisomerization
 of Allenynes: Selective Preparation of Monocyclic,
 Bicyclo[m.3.0], and Bicyclo[5.2.0] Ring Systems
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7159
_journal_page_last               7171
_journal_paper_doi               10.1021/jo050770z
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C23 H24 O2 S'
_chemical_formula_weight         364.50
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.615(1)
_cell_length_b                   15.929(1)
_cell_length_c                   8.391(2)
_cell_volume                     1953.3(5)
_exptl_crystal_density_diffrn    1.239
_cod_original_formula_sum        'C23 H24 O2 S '
_cod_database_code               4020440
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
1/2-x,-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
S(1) 0.60404(8) 0.38164(8) 0.3637(1)
O(1) 0.5700(3) 0.4623(3) 0.4132(6)
O(2) 0.6719(2) 0.3411(3) 0.4604(5)
C(1) 0.6499(3) 0.3922(2) 0.1658(5)
C(2) 0.7217(4) 0.4632(3) 0.1668(7)
C(3) 0.8161(3) 0.4406(3) 0.2293(7)
C(4) 0.8640(3) 0.3712(3) 0.1387(3)
C(5) 0.8360(4) 0.2816(3) 0.1866(8)
C(6) 0.7478(2) 0.2498(4) 0.1201(6)
C(7) 0.6764(2) 0.3109(2) 0.0852(5)
C(8) 0.6137(3) 0.3210(3) -0.0311(5)
C(9) 0.5749(3) 0.4012(3) 0.0361(6)
C(10) 0.5084(3) 0.3134(3) 0.3482(6)
C(11) 0.4213(3) 0.3465(3) 0.3508(8)
C(12) 0.3471(4) 0.2920(4) 0.3382(8)
C(13) 0.3593(4) 0.2083(4) 0.3233(8)
C(14) 0.4471(5) 0.1758(4) 0.3180(1)
C(15) 0.5220(4) 0.2287(3) 0.3336(8)
C(16) 0.7331(3) 0.1682(3) 0.0859(6)
C(17) 0.7948(3) 0.0963(2) 0.1041(4)
C(18) 0.7886(4) 0.0310(3) -0.0040(1)
C(19) 0.8423(4) -0.0381(3) 0.0045(9)
C(20) 0.9040(3) -0.0470(3) 0.1250(8)
C(21) 0.9120(3) 0.0145(3) 0.2357(7)
C(22) 0.8574(3) 0.0857(3) 0.2259(7)
C(23) 0.5919(3) 0.2753(4) -0.1807(7)
H(1) 0.722(3) 0.485(3) 0.055(7)
H(2) 0.692(4) 0.512(4) 0.233(8)
H(3) 0.812(4) 0.416(4) 0.370(8)
H(4) 0.858(4) 0.495(3) 0.216(6)
H(5) 0.931(3) 0.372(3) 0.173(6)
H(6) 0.854(4) 0.378(3) 0.021(8)
H(7) 0.845(3) 0.273(3) 0.290(6)
H(8) 0.890(4) 0.246(3) 0.167(6)
H(9) 0.515(3) 0.396(3) 0.069(5)
H(10) 0.582(3) 0.466(3) -0.004(6)
H(11) 0.418(4) 0.402(4) 0.316(7)
H(12) 0.278(4) 0.313(4) 0.336(8)
H(13) 0.308(4) 0.160(3) 0.299(7)
H(14) 0.463(4) 0.119(3) 0.320(6)
H(15) 0.584(7) 0.219(6) 0.36(1)
H(16) 0.676(3) 0.146(3) 0.029(6)
H(17) 0.753(4) 0.030(3) -0.083(7)
H(18) 0.833(5) -0.090(3) -0.10(1)
H(19) 0.936(4) -0.107(4) 0.116(8)
H(20) 0.958(3) 0.006(3) 0.325(6)
H(21) 0.855(4) 0.126(3) 0.297(7)
H(22) 0.5423 0.3028 -0.2329
H(23) 0.6442 0.2771 -0.2498
H(24) 0.5767 0.2195 -0.1584
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S(1) O(1) 1.439(4)
S(1) O(2) 1.435(4)
S(1) C(1) 1.798(4)
S(1) C(10) 1.775(5)
C(1) C(2) 1.543(6)
C(1) C(7) 1.511(6)
C(1) C(9) 1.551(6)
C(2) C(3) 1.520(7)
C(2) H(1) 1.00(6)
C(2) H(2) 1.05(6)
C(3) C(4) 1.514(8)
C(3) H(3) 1.25(7)
C(3) H(4) 1.07(5)
C(4) C(5) 1.536(7)
C(4) H(5) 1.02(5)
C(4) H(6) 1.00(6)
C(5) C(6) 1.496(6)
C(5) H(7) 0.89(5)
C(5) H(8) 0.99(5)
C(6) C(7) 1.457(6)
C(6) C(16) 1.348(6)
C(7) C(8) 1.348(6)
C(8) C(9) 1.508(6)
C(8) C(23) 1.486(7)
C(9) H(9) 0.92(5)
C(9) H(10) 1.09(5)
C(10) C(11) 1.378(6)
C(10) C(15) 1.369(7)
C(11) C(12) 1.393(7)
C(11) H(11) 0.94(6)
C(12) C(13) 1.351(8)
C(12) H(12) 1.06(6)
C(13) C(14) 1.385(6)
C(13) H(13) 1.09(6)
C(14) C(15) 1.388(8)
C(14) H(14) 0.94(5)
C(15) H(15) 0.9(1)
C(16) C(17) 1.466(6)
C(16) H(16) 1.02(5)
C(17) C(18) 1.386(7)
C(17) C(22) 1.383(7)
C(18) C(19) 1.354(8)
C(18) H(17) 0.84(6)
C(19) C(20) 1.362(9)
C(19) H(18) 1.20(8)
C(20) C(21) 1.355(8)
C(20) H(19) 1.07(6)
C(21) C(22) 1.390(7)
C(21) H(20) 1.02(5)
C(22) H(21) 0.88(6)
C(23) H(22) 0.954
C(23) H(23) 0.961
C(23) H(24) 0.935
