#------------------------------------------------------------------------------
#$Date: 2015-01-27 21:58:39 +0200 (Tue, 27 Jan 2015) $
#$Revision: 130149 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/05/4020543.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_4020543
loop_
_publ_author_name
'Philippe James'
'François-Xavier Felpin'
'Yannick Landais'
'Kurt Schenk'
_publ_section_title
;
 Free-Radical-5-exo-Trig Cyclization of Chiral
 3-Silylhepta-1,6-dienes: Concise Approach to the
 A-B-C Ring Core of Hexacyclinic Acid
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7985
_journal_page_last               7995
_journal_paper_doi               10.1021/jo051062g
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C22 H23 N O6 S'
_chemical_formula_weight         429.47
_space_group_IT_number           41
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C -2ac 2'
_symmetry_space_group_name_H-M   'C 2 c b'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   7.680
_cell_length_b                   25.480
_cell_length_c                   42.460
_cell_measurement_temperature    293(2)
_cell_volume                     8308.8
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.373
_cod_database_code               4020543
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, y, -z+1/2'
'x, -y, -z'
'x+1/2, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'x+1, -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_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
S1 S 1.5375(5) 0.73463(12) 0.91083(8) 0.0276(8) Uani 1 1 d U . .
O11C O 0.643(3) 0.7240(5) 0.7560(3) 0.027(4) Uani 0.75(4) 1 d PU . .
O11D O 0.645(3) 0.8007(4) 0.7789(3) 0.019(4) Uani 0.75(4) 1 d PU . .
O12C O 0.741(9) 0.8040(14) 0.7749(10) 0.031(13) Uani 0.25(4) 1 d PU . .
O12D O 0.718(7) 0.7337(15) 0.7519(10) 0.020(12) Uani 0.25(4) 1 d PU . .
O13 O 1.6285(12) 0.6958(3) 0.9295(2) 0.035(2) Uani 1 1 d U . .
O14 O 1.6313(13) 0.7812(3) 0.9018(2) 0.034(2) Uani 1 1 d U . .
O15 O 1.0795(10) 0.6909(3) 0.90540(18) 0.0138(19) Uani 1 1 d U . .
O16 O 1.0141(11) 0.6114(3) 0.88739(19) 0.023(2) Uani 1 1 d U . .
N1 N 0.6953(16) 0.7548(4) 0.7771(3) 0.037(3) Uani 1 1 d U . .
C1 C 1.3480(17) 0.7552(4) 0.9317(3) 0.025(3) Uani 1 1 d U . .
H1B H 1.3802 0.7835 0.9458 0.030 Uiso 1 1 calc R . .
H1A H 1.2649 0.7692 0.9167 0.030 Uiso 1 1 calc R . .
C2 C 1.2582(17) 0.7122(4) 0.9509(3) 0.023(3) Uani 1 1 d U . .
H2 H 1.3497 0.6946 0.9631 0.028 Uiso 1 1 calc R . .
C3 C 1.1245(19) 0.7329(5) 0.9750(3) 0.029(3) Uani 1 1 d U . .
H3 H 1.1862 0.7484 0.9930 0.035 Uiso 1 1 calc R . .
C4 C 1.032(2) 0.6818(5) 0.9858(3) 0.036(3) Uani 1 1 d U . .
H4A H 1.0973 0.6647 1.0024 0.043 Uiso 1 1 calc R . .
H4B H 0.9156 0.6895 0.9935 0.043 Uiso 1 1 calc R . .
C5 C 1.0233(17) 0.6468(4) 0.9561(3) 0.020(3) Uani 1 1 d U . .
H5A H 1.0502 0.6107 0.9614 0.024 Uiso 1 1 calc R . .
H5B H 0.9080 0.6481 0.9468 0.024 Uiso 1 1 calc R . .
C6 C 1.1602(14) 0.6692(4) 0.9331(2) 0.006(2) Uani 1 1 d U . .
H6 H 1.2416 0.6414 0.9270 0.008 Uiso 1 1 calc R . .
C7 C 0.9939(17) 0.7723(4) 0.9622(3) 0.021(3) Uani 1 1 d U . .
H7 H 0.9193 0.7620 0.9461 0.026 Uiso 1 1 calc R . .
C8 C 0.9824(18) 0.8219(4) 0.9733(3) 0.026(3) Uani 1 1 d U . .
H8A H 1.0559 0.8329 0.9894 0.031 Uiso 1 1 calc R . .
H8B H 0.9009 0.8449 0.9648 0.031 Uiso 1 1 calc R . .
C10 C 1.0127(16) 0.6590(4) 0.8846(3) 0.017(3) Uani 1 1 d U . .
C11 C 0.9306(16) 0.7416(4) 0.8541(3) 0.013(3) Uani 1 1 d U . .
H11 H 0.9751 0.7628 0.8700 0.016 Uiso 1 1 calc R . .
C12 C 0.8538(17) 0.7633(4) 0.8276(3) 0.023(3) Uani 1 1 d U . .
H12 H 0.8452 0.7995 0.8254 0.028 Uiso 1 1 calc R . .
C13 C 0.7899(18) 0.7301(4) 0.8044(3) 0.023(3) Uani 1 1 d U . .
C14 C 0.8026(18) 0.6782(5) 0.8058(3) 0.029(3) Uani 1 1 d U . .
H14 H 0.7618 0.6580 0.7891 0.034 Uiso 1 1 calc R . .
C15 C 0.8764(15) 0.6538(4) 0.8318(3) 0.016(3) Uani 1 1 d U . .
H15 H 0.8840 0.6175 0.8331 0.019 Uiso 1 1 calc R . .
C16 C 0.9397(16) 0.6866(4) 0.8562(3) 0.013(3) Uani 1 1 d U . .
C17 C 1.4611(16) 0.7024(4) 0.8759(3) 0.017(3) Uani 1 1 d U . .
C18 C 1.3948(15) 0.7310(4) 0.8504(3) 0.017(3) Uani 1 1 d U . .
H18 H 1.3881 0.7673 0.8520 0.021 Uiso 1 1 calc R . .
C19 C 1.3405(18) 0.7078(4) 0.8237(3) 0.027(3) Uani 1 1 d U . .
H19 H 1.2938 0.7277 0.8074 0.033 Uiso 1 1 calc R . .
C20 C 1.3559(19) 0.6518(5) 0.8207(3) 0.037(4) Uani 1 1 d U . .
C21 C 1.4252(18) 0.6258(5) 0.8453(3) 0.027(3) Uani 1 1 d U . .
H21 H 1.4386 0.5897 0.8432 0.033 Uiso 1 1 calc R . .
C22 C 1.4779(17) 0.6482(5) 0.8732(3) 0.029(3) Uani 1 1 d U . .
H22 H 1.5226 0.6280 0.8896 0.034 Uiso 1 1 calc R . .
C23 C 1.305(2) 0.6244(5) 0.7908(3) 0.041(4) Uani 1 1 d U . .
H23A H 1.1958 0.6382 0.7835 0.061 Uiso 1 1 calc R . .
H23B H 1.2931 0.5875 0.7947 0.061 Uiso 1 1 calc R . .
H23C H 1.3929 0.6301 0.7751 0.061 Uiso 1 1 calc R . .
S1A S 0.8206(4) 0.95076(10) 0.83713(7) 0.0186(7) Uani 1 1 d U . .
O11A O 0.041(3) 1.0954(8) 0.9549(5) 0.057(7) Uani 0.519(14) 1 d PU . .
O11B O 0.159(3) 1.0859(7) 0.9740(4) 0.039(6) Uani 0.519(14) 1 d PU . .
O12A O -0.067(3) 1.0329(9) 0.9811(6) 0.050(8) Uani 0.481(14) 1 d PU . .
O12B O -0.102(3) 1.0563(8) 0.9749(5) 0.029(6) Uani 0.481(14) 1 d PU . .
O13A O 0.8803(10) 0.8985(3) 0.8294(2) 0.024(2) Uani 1 1 d U . .
O14A O 0.9383(11) 0.9938(3) 0.8345(2) 0.0217(19) Uani 1 1 d U . .
O15A O 0.3499(11) 0.9236(3) 0.84696(17) 0.0144(18) Uani 1 1 d U . .
O16A O 0.2577(11) 0.8545(3) 0.87674(19) 0.024(2) Uani 1 1 d U . .
N1A N 0.0337(18) 1.0514(4) 0.9620(3) 0.038(3) Uani 1 1 d U . .
C1A C 0.6373(15) 0.9671(4) 0.8131(3) 0.012(2) Uani 1 1 d U . .
H12A H 0.5609 0.9898 0.8251 0.015 Uiso 1 1 calc R . .
H12B H 0.6786 0.9872 0.7952 0.015 Uiso 1 1 calc R . .
C2A C 0.5302(16) 0.9209(4) 0.8007(3) 0.014(3) Uani 1 1 d U . .
H2B H 0.6111 0.8971 0.7900 0.017 Uiso 1 1 calc R . .
C3A C 0.3890(16) 0.9375(4) 0.7760(3) 0.026(3) Uani 1 1 d U . .
H3B H 0.4459 0.9456 0.7559 0.031 Uiso 1 1 calc R . .
C4A C 0.285(2) 0.8870(5) 0.7727(3) 0.044(4) Uani 1 1 d U . .
H4D H 0.3365 0.8650 0.7565 0.053 Uiso 1 1 calc R . .
H4C H 0.1662 0.8948 0.7668 0.053 Uiso 1 1 calc R . .
C5A C 0.2895(19) 0.8579(4) 0.8052(3) 0.020(3) Uani 1 1 d U . .
H5D H 0.155(16) 0.877(4) 0.810(3) 0.024 Uiso 1 1 d . . .
H5C H 0.319(15) 0.823(4) 0.801(3) 0.024 Uiso 1 1 d . . .
C6A C 0.4272(16) 0.8876(4) 0.8248(3) 0.012(3) Uani 1 1 d U . .
H6B H 0.5045 0.8629 0.8356 0.014 Uiso 1 1 calc R . .
C7A C 0.2832(17) 0.9828(4) 0.7859(3) 0.021(3) Uani 1 1 d U . .
H7B H 0.2042 0.9781 0.8023 0.00(3) Uiso 1 1 calc R . .
C8A C 0.2941(19) 1.0290(5) 0.7731(3) 0.036(4) Uani 1 1 d U . .
H8AA H 0.3720 1.0348 0.7567 0.043 Uiso 1 1 calc R . .
H8AB H 0.2240 1.0562 0.7804 0.043 Uiso 1 1 calc R . .
C10A C 0.2712(16) 0.9018(4) 0.8728(3) 0.018(3) Uani 1 1 d U . .
C11A C 0.2490(15) 0.9961(4) 0.8916(3) 0.012(3) Uani 1 1 d U . .
H11B H 0.3098 1.0075 0.8739 0.015 Uiso 1 1 calc R . .
C12A C 0.1946(17) 1.0313(5) 0.9139(3) 0.029(3) Uani 1 1 d U . .
H12B H 0.2235 1.0666 0.9122 0.035 Uiso 1 1 calc R . .
C13A C 0.0980(16) 1.0138(5) 0.9384(3) 0.023(3) Uani 1 1 d U . .
C14B C 0.0547(19) 0.9612(5) 0.9437(3) 0.032(3) Uani 1 1 d U . .
H14B H -0.0107 0.9507 0.9610 0.038 Uiso 1 1 calc R . .
C15A C 0.1158(15) 0.9254(4) 0.9213(3) 0.015(3) Uani 1 1 d U . .
H15B H 0.0917 0.8898 0.9236 0.018 Uiso 1 1 calc R . .
C16A C 0.2120(16) 0.9425(4) 0.8957(3) 0.014(3) Uani 1 1 d U . .
C17A C 0.7389(17) 0.9495(4) 0.8760(3) 0.021(3) Uani 1 1 d U . .
C18A C 0.7119(17) 0.9962(4) 0.8914(3) 0.024(3) Uani 1 1 d U . .
H18B H 0.7370 1.0277 0.8814 0.028 Uiso 1 1 calc R . .
C19A C 0.6461(16) 0.9962(4) 0.9223(3) 0.021(3) Uani 1 1 d U . .
H19B H 0.6297 1.0278 0.9328 0.025 Uiso 1 1 calc R . .
C20A C 0.6053(16) 0.9491(5) 0.9372(3) 0.022(3) Uani 1 1 d U . .
C21A C 0.6361(17) 0.9018(5) 0.9213(3) 0.023(3) Uani 1 1 d U . .
H21B H 0.6090 0.8702 0.9311 0.027 Uiso 1 1 calc R . .
C22A C 0.7048(17) 0.9012(5) 0.8917(3) 0.026(3) Uani 1 1 d U . .
H22B H 0.7293 0.8695 0.8818 0.032 Uiso 1 1 calc R . .
C23A C 0.5310(18) 0.9501(5) 0.9699(3) 0.031(3) Uani 1 1 d U . .
H23F H 0.5130 0.9148 0.9771 0.047 Uiso 1 1 calc R . .
H23E H 0.4219 0.9685 0.9697 0.047 Uiso 1 1 calc R . .
H23D H 0.6106 0.9677 0.9838 0.047 Uiso 1 1 calc R . .
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 O14 1.439(9) . ?
S1 O13 1.448(9) . ?
S1 C1 1.783(13) . ?
S1 C17 1.794(12) . ?
O11C O12D 0.65(5) . ?
O11C N1 1.258(17) . ?
O11D O12C 0.76(6) . ?
O11D N1 1.236(14) . ?
O12C N1 1.31(4) . ?
O12D N1 1.21(4) . ?
O15 C10 1.306(13) . ?
O15 C6 1.440(12) . ?
O16 C10 1.217(12) . ?
N1 C13 1.505(16) . ?
C1 C2 1.530(16) . ?
C2 C6 1.530(15) . ?
C2 C3 1.542(18) . ?
C3 C7 1.521(17) . ?
C3 C4 1.552(17) . ?
C4 C5 1.545(16) . ?
C5 C6 1.544(15) . ?
C7 C8 1.350(15) . ?
C10 C16 1.504(15) . ?
C11 C12 1.383(16) . ?
C11 C16 1.404(13) . ?
C12 C13 1.388(16) . ?
C13 C14 1.326(16) . ?
C14 C15 1.389(17) . ?
C15 C16 1.418(15) . ?
C17 C22 1.394(15) . ?
C17 C18 1.398(15) . ?
C18 C19 1.345(16) . ?
C19 C20 1.437(17) . ?
C20 C21 1.345(18) . ?
C20 C23 1.502(18) . ?
C21 C22 1.378(17) . ?
S1A O14A 1.426(8) . ?
S1A O13A 1.445(8) . ?
S1A C17A 1.764(13) . ?
S1A C1A 1.788(12) . ?
O11A N1A 1.16(2) . ?
O11A O11B 1.24(3) . ?
O11A O12B 1.71(3) . ?
O11B N1A 1.40(2) . ?
O12A O12B 0.70(3) . ?
O12A N1A 1.22(3) . ?
O12B N1A 1.18(2) . ?
O15A C10A 1.371(14) . ?
O15A C6A 1.443(12) . ?
O16A C10A 1.223(13) . ?
N1A C13A 1.471(16) . ?
C1A C2A 1.530(14) . ?
C2A C6A 1.543(15) . ?
C2A C3A 1.568(16) . ?
C3A C7A 1.472(16) . ?
C3A C4A 1.520(18) . ?
C4A C5A 1.568(17) . ?
C5A C6A 1.542(17) . ?
C7A C8A 1.298(16) . ?
C10A C16A 1.490(15) . ?
C11A C12A 1.368(15) . ?
C11A C16A 1.406(14) . ?
C12A C13A 1.353(17) . ?
C13A C14B 1.400(17) . ?
C14B C15A 1.399(17) . ?
C15A C16A 1.385(16) . ?
C17A C18A 1.374(16) . ?
C17A C22A 1.423(16) . ?
C18A C19A 1.405(17) . ?
C19A C20A 1.395(16) . ?
C20A C21A 1.401(16) . ?
C20A C23A 1.500(17) . ?
C21A C22A 1.363(17) . ?
