#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/59/1505959.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_1505959
loop_
_publ_author_name
'El-Awa, Ahmad'
'Fuchs, Philip'
_publ_section_title
;
 Double lawton SN2'addition to epoxyvinyl sulfones: selective construction
 of the stereotetrads of aplyronine A.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2905
_journal_page_last               2908
_journal_paper_doi               10.1021/ol060530l
_journal_volume                  8
_journal_year                    2006
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C27 H48 O4 S1 Si2'
_chemical_formula_sum            'C27 H48 O4 S Si2'
_chemical_formula_weight         524.92
_chemical_name_systematic        ' ?'
_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'
_atom_type_scat_source
'International Tables for Crystallography (Vol C)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3367(8)
_cell_length_b                   10.7685(7)
_cell_length_c                   28.627(2)
_cell_measurement_reflns_used    9579
_cell_measurement_temperature    150
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     3186.5(4)
_computing_cell_refinement       DENZO/SCALEPACK_(Otwinowski,_1996)
_computing_data_collection       Collect_(Nonius,_1998)
_computing_data_reduction        DENZO/SCALEPACK_(Otwinowski,_1996)
_computing_molecular_graphics
;
    ORTEP (Johnson, 1976)
    PLATON (Spek, 1997)
;
_computing_structure_refinement  SHELX97_(Sheldrick,_1997)
_computing_structure_solution    Direct_methods_(SIR2002,_Burla_et_al.,_2003)
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.9894
_diffrn_measured_fraction_theta_max 0.9618
_diffrn_measurement_device_type  Nonius_KappaCCD
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'graphite 002'
_diffrn_radiation_type           MO-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.095
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9579
_diffrn_reflns_theta_full        23.3
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.9663
_exptl_absorpt_correction_T_min  0.9221
_exptl_absorpt_correction_type   multi-scan_(Otwinowski_&_Minor,_1997)
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_description       plate
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.71
_refine_diff_density_min         -0.35
_refine_ls_abs_structure_details
'Flack H. D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         2928
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.112
_refine_ls_R_factor_gt           0.097
_refine_ls_shift/su_max          0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[σ²(Fo²)+(0.0448P)²+13.5183P] where P=(Fo²+2Fc²)/3 '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.205
_refine_ls_wR_factor_ref         0.216
_reflns_Friedel_coverage         0.8432
_reflns_number_gt                2542
_reflns_number_total             5318
_reflns_threshold_expression     >2.0σ(I)
_cod_data_source_file            ol060530lrom20060303_101006.cif
_cod_data_source_block           3462
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc ' changed to 'calc'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_formula_sum        'C27 H48 O4 S1 Si2'
_cod_database_code               1505959
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
S(1) S 0.8345(3) 0.9584(3) 0.98415(10) 0.0758(10) Uani 1 1 d .
Si(3) Si 0.6383(4) 1.2268(3) 1.13932(13) 0.0826(11) Uani 1 1 d .
Si(5) Si 0.9535(4) 0.7635(5) 1.17776(13) 0.1064(16) Uani 1 1 d .
O(3) O 0.5874(6) 1.0903(6) 1.1214(2) 0.060(2) Uani 1 1 d .
O(5) O 0.8543(6) 0.7975(6) 1.1358(2) 0.068(2) Uani 1 1 d .
O(11) O 0.9066(9) 0.8594(8) 0.9620(3) 0.103(3) Uani 1 1 d .
O(12) O 0.7512(8) 1.0359(8) 0.9568(2) 0.090(3) Uani 1 1 d .
C(1) C 0.7429(11) 0.8910(11) 1.0303(4) 0.064(3) Uani 1 1 d .
C(2) C 0.6478(9) 0.9781(9) 1.0525(3) 0.053(3) Uani 1 1 d .
C(3) C 0.6649(9) 0.9871(9) 1.1057(3) 0.055(3) Uani 1 1 d .
C(4) C 0.6365(10) 0.8777(9) 1.1367(4) 0.065(3) Uani 1 1 d .
C(5) C 0.7207(11) 0.7645(11) 1.1287(4) 0.077(3) Uani 1 1 d .
C(6) C 0.7051(11) 0.7030(10) 1.0804(5) 0.081(4) Uani 1 1 d .
C(7) C 0.7670(10) 0.7725(11) 1.0417(4) 0.070(3) Uani 1 1 d .
C(11) C 0.9472(13) 1.0569(15) 1.0152(4) 0.078(3) Uani 1 1 d .
C(12) C 1.0483(15) 1.0008(15) 1.0348(5) 0.095(4) Uani 1 1 d .
C(13) C 1.1319(16) 1.075(3) 1.0592(6) 0.137(7) Uani 1 1 d .
C(14) C 1.111(2) 1.203(3) 1.0616(7) 0.150(9) Uani 1 1 d .
C(15) C 1.007(2) 1.2574(18) 1.0406(6) 0.131(6) Uani 1 1 d .
C(16) C 0.9264(14) 1.1834(15) 1.0171(4) 0.092(4) Uani 1 1 d .
C(21) C 0.5073(10) 0.9501(11) 1.0341(4) 0.076(3) Uani 1 1 d .
C(31) C 0.5196(16) 1.2868(17) 1.1774(5) 0.123(6) Uani 1 1 d .
C(32) C 0.5060(15) 1.1781(17) 1.2202(4) 0.138(7) Uani 1 1 d .
C(33) C 0.544(2) 1.4214(15) 1.1933(8) 0.182(10) Uani 1 1 d .
C(34) C 0.3750(13) 1.2870(15) 1.1509(5) 0.121(5) Uani 1 1 d .
C(35) C 0.7941(12) 1.2077(11) 1.1680(4) 0.089(4) Uani 1 1 d .
C(36) C 0.6392(18) 1.3441(13) 1.0886(5) 0.129(6) Uani 1 1 d .
C(41) C 0.4931(10) 0.8394(11) 1.1404(4) 0.080(4) Uani 1 1 d .
C(51) C 1.0717(13) 0.6504(15) 1.1590(5) 0.101(5) Uani 1 1 d .
C(52) C 1.1372(15) 0.716(2) 1.1122(5) 0.197(12) Uani 1 1 d .
C(53) C 0.989(2) 0.5297(13) 1.1513(9) 0.220(12) Uani 1 1 d .
C(54) C 1.1809(15) 0.6380(19) 1.1952(5) 0.152(8) Uani 1 1 d .
C(55) C 0.8742(15) 0.732(3) 1.2324(5) 0.201(12) Uani 1 1 d .
C(56) C 1.056(2) 0.9198(13) 1.1869(7) 0.196(12) Uani 1 1 d .
H(2) H 0.6700 1.0623 1.0401 0.064 Uiso 1 1 calc R
H(3) H 0.7572 1.0104 1.1114 0.066 Uiso 1 1 calc R
H(4) H 0.6597 0.9066 1.1688 0.078 Uiso 1 1 calc R
H(5) H 0.6971 0.7013 1.1529 0.092 Uiso 1 1 calc R
H(7) H 0.8291 0.7293 1.0234 0.084 Uiso 1 1 calc R
H(12) H 1.0617 0.9139 1.0320 0.114 Uiso 1 1 calc R
H(13) H 1.2044 1.0395 1.0746 0.164 Uiso 1 1 calc R
H(14) H 1.1709 1.2538 1.0782 0.181 Uiso 1 1 calc R
H(15) H 0.9925 1.3444 1.0427 0.158 Uiso 1 1 calc R
H(16) H 0.8539 1.2182 1.0014 0.111 Uiso 1 1 calc R
H(6A) H 0.7428 0.6185 1.0816 0.097 Uiso 1 1 calc R
H(6B) H 0.6117 0.6942 1.0735 0.097 Uiso 1 1 calc R
H(21A) H 0.5023 0.9695 1.0007 0.114 Uiso 1 1 calc R
H(21B) H 0.4449 1.0012 1.0513 0.114 Uiso 1 1 calc R
H(21C) H 0.4873 0.8621 1.0390 0.114 Uiso 1 1 calc R
H(32A) H 0.5833 1.1804 1.2401 0.207 Uiso 1 1 calc R
H(32B) H 0.4977 1.0956 1.2061 0.207 Uiso 1 1 calc R
H(32C) H 0.4293 1.1958 1.2392 0.207 Uiso 1 1 calc R
H(33A) H 0.5638 1.4732 1.1661 0.273 Uiso 1 1 calc R
H(33B) H 0.6173 1.4232 1.2151 0.273 Uiso 1 1 calc R
H(33C) H 0.4667 1.4536 1.2090 0.273 Uiso 1 1 calc R
H(34A) H 0.3096 1.3208 1.1722 0.181 Uiso 1 1 calc R
H(34B) H 0.3515 1.2018 1.1423 0.181 Uiso 1 1 calc R
H(34C) H 0.3792 1.3384 1.1227 0.181 Uiso 1 1 calc R
H(35A) H 0.7891 1.1389 1.1903 0.134 Uiso 1 1 calc R
H(35B) H 0.8167 1.2844 1.1845 0.134 Uiso 1 1 calc R
H(35C) H 0.8605 1.1895 1.1445 0.134 Uiso 1 1 calc R
H(36A) H 0.7243 1.3434 1.0734 0.193 Uiso 1 1 calc R
H(36B) H 0.6212 1.4275 1.1007 0.193 Uiso 1 1 calc R
H(36C) H 0.5727 1.3211 1.0658 0.193 Uiso 1 1 calc R
H(41A) H 0.4394 0.9137 1.1441 0.120 Uiso 1 1 calc R
H(41B) H 0.4814 0.7848 1.1675 0.120 Uiso 1 1 calc R
H(41C) H 0.4674 0.7952 1.1119 0.120 Uiso 1 1 calc R
H(52A) H 1.1683 0.7989 1.1201 0.296 Uiso 1 1 calc R
H(52B) H 1.0721 0.7215 1.0874 0.296 Uiso 1 1 calc R
H(52C) H 1.2099 0.6647 1.1013 0.296 Uiso 1 1 calc R
H(53A) H 1.0464 0.4616 1.1417 0.329 Uiso 1 1 calc R
H(53B) H 0.9246 0.5447 1.1270 0.329 Uiso 1 1 calc R
H(53C) H 0.9459 0.5073 1.1806 0.329 Uiso 1 1 calc R
H(54A) H 1.1494 0.5914 1.2223 0.228 Uiso 1 1 calc R
H(54B) H 1.2088 0.7208 1.2051 0.228 Uiso 1 1 calc R
H(54C) H 1.2542 0.5939 1.1811 0.228 Uiso 1 1 calc R
H(55A) H 0.8174 0.8012 1.2406 0.301 Uiso 1 1 calc R
H(55B) H 0.9393 0.7205 1.2569 0.301 Uiso 1 1 calc R
H(55C) H 0.8226 0.6556 1.2295 0.301 Uiso 1 1 calc R
H(56A) H 1.1480 0.9014 1.1839 0.294 Uiso 1 1 calc R
H(56B) H 1.0381 0.9535 1.2181 0.294 Uiso 1 1 calc R
H(56C) H 1.0304 0.9808 1.1632 0.294 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_radius_bond
S 1.02
Si 1.11
O 0.73
C 0.77
H 0.32
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O(12) S(1) O(11) 120.0(5)
O(12) S(1) C(1) 108.9(5)
O(11) S(1) C(1) 107.4(6)
O(12) S(1) C(11) 108.3(7)
O(11) S(1) C(11) 108.4(7)
C(1) S(1) C(11) 102.5(5)
O(3) Si(3) C(31) 107.4(7)
O(3) Si(3) C(35) 108.8(5)
C(31) Si(3) C(35) 112.3(6)
O(3) Si(3) C(36) 110.6(6)
C(31) Si(3) C(36) 103.3(8)
C(35) Si(3) C(36) 114.2(7)
O(5) Si(5) C(55) 113.5(6)
O(5) Si(5) C(51) 111.1(5)
C(55) Si(5) C(51) 115.9(9)
O(5) Si(5) C(56) 103.9(6)
C(55) Si(5) C(56) 106.7(11)
C(51) Si(5) C(56) 104.4(8)
C(3) O(3) Si(3) 127.5(6)
C(5) O(5) Si(5) 130.9(7)
C(7) C(1) C(2) 127.9(11)
C(7) C(1) S(1) 118.1(9)
C(2) C(1) S(1) 114.0(8)
C(1) C(2) C(3) 112.6(8)
C(1) C(2) C(21) 110.1(9)
C(3) C(2) C(21) 116.7(8)
O(3) C(3) C(4) 108.2(8)
O(3) C(3) C(2) 107.0(7)
C(4) C(3) C(2) 120.8(9)
C(3) C(4) C(5) 115.4(9)
C(3) C(4) C(41) 116.0(9)
C(5) C(4) C(41) 110.3(9)
O(5) C(5) C(4) 109.3(9)
O(5) C(5) C(6) 109.4(9)
C(4) C(5) C(6) 114.9(10)
C(7) C(6) C(5) 114.1(9)
C(1) C(7) C(6) 125.7(11)
C(12) C(11) C(16) 123.7(14)
C(12) C(11) S(1) 116.5(13)
C(16) C(11) S(1) 119.8(11)
C(11) C(12) C(13) 116.4(17)
C(12) C(13) C(14) 120.3(17)
C(15) C(14) C(13) 121.4(19)
C(16) C(15) C(14) 117.4(19)
C(15) C(16) C(11) 120.7(16)
C(33) C(31) C(34) 106.2(14)
C(33) C(31) C(32) 116.6(13)
C(34) C(31) C(32) 104.7(12)
C(33) C(31) Si(3) 114.4(13)
C(34) C(31) Si(3) 110.0(8)
C(32) C(31) Si(3) 104.5(11)
C(54) C(51) C(53) 114.9(15)
C(54) C(51) C(52) 106.3(12)
C(53) C(51) C(52) 117.3(15)
C(54) C(51) Si(5) 110.8(10)
C(53) C(51) Si(5) 103.5(11)
C(52) C(51) Si(5) 103.4(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S(1) O(12) 1.433(8)
S(1) O(11) 1.447(8)
S(1) C(1) 1.780(12)
S(1) C(11) 1.810(14)
Si(3) O(3) 1.643(7)
Si(3) C(31) 1.764(16)
Si(3) C(35) 1.819(12)
Si(3) C(36) 1.925(13)
Si(5) O(5) 1.621(7)
Si(5) C(55) 1.799(15)
Si(5) C(51) 1.807(14)
Si(5) C(56) 2.003(16)
O(3) C(3) 1.441(11)
O(5) C(5) 1.441(13)
C(1) C(7) 1.340(14)
C(1) C(2) 1.500(14)
C(2) C(3) 1.538(13)
C(2) C(21) 1.573(14)
C(3) C(4) 1.504(14)
C(4) C(5) 1.515(14)
C(4) C(41) 1.542(14)
C(5) C(6) 1.542(16)
C(6) C(7) 1.482(15)
C(11) C(12) 1.330(17)
C(11) C(16) 1.379(18)
C(12) C(13) 1.37(2)
C(13) C(14) 1.40(3)
C(14) C(15) 1.36(2)
C(15) C(16) 1.337(19)
C(31) C(33) 1.54(2)
C(31) C(34) 1.676(19)
C(31) C(32) 1.70(2)
C(51) C(54) 1.537(17)
C(51) C(53) 1.57(2)
C(51) C(52) 1.66(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C(31) Si(3) O(3) C(3) -153.8(9)
C(35) Si(3) O(3) C(3) -32.1(9)
C(36) Si(3) O(3) C(3) 94.1(9)
C(55) Si(5) O(5) C(5) -26.0(14)
C(51) Si(5) O(5) C(5) 106.8(10)
C(56) Si(5) O(5) C(5) -141.5(11)
O(12) S(1) C(1) C(7) 140.8(9)
O(11) S(1) C(1) C(7) 9.5(10)
C(11) S(1) C(1) C(7) -104.6(10)
O(12) S(1) C(1) C(2) -40.3(9)
O(11) S(1) C(1) C(2) -171.6(8)
C(11) S(1) C(1) C(2) 74.3(9)
C(7) C(1) C(2) C(3) 53.0(15)
S(1) C(1) C(2) C(3) -125.7(8)
C(7) C(1) C(2) C(21) -79.0(13)
S(1) C(1) C(2) C(21) 102.2(9)
Si(3) O(3) C(3) C(4) 121.1(8)
Si(3) O(3) C(3) C(2) -107.2(8)
C(1) C(2) C(3) O(3) 168.7(8)
C(21) C(2) C(3) O(3) -62.6(11)
C(1) C(2) C(3) C(4) -67.0(12)
C(21) C(2) C(3) C(4) 61.7(12)
O(3) C(3) C(4) C(5) -173.4(9)
C(2) C(3) C(4) C(5) 62.8(13)
O(3) C(3) C(4) C(41) 55.3(12)
C(2) C(3) C(4) C(41) -68.4(13)
Si(5) O(5) C(5) C(4) 107.7(10)
Si(5) O(5) C(5) C(6) -125.7(9)
C(3) C(4) C(5) O(5) 58.9(13)
C(41) C(4) C(5) O(5) -167.2(9)
C(3) C(4) C(5) C(6) -64.5(13)
C(41) C(4) C(5) C(6) 69.4(12)
O(5) C(5) C(6) C(7) -48.6(12)
C(4) C(5) C(6) C(7) 74.7(12)
C(2) C(1) C(7) C(6) -1.8(18)
S(1) C(1) C(7) C(6) 177.0(9)
C(5) C(6) C(7) C(1) -56.5(15)
O(12) S(1) C(11) C(12) -166.7(9)
O(11) S(1) C(11) C(12) -35.0(11)
C(1) S(1) C(11) C(12) 78.3(11)
O(12) S(1) C(11) C(16) 12.5(12)
O(11) S(1) C(11) C(16) 144.1(10)
C(1) S(1) C(11) C(16) -102.5(11)
C(16) C(11) C(12) C(13) 2(2)
S(1) C(11) C(12) C(13) -178.6(10)
C(11) C(12) C(13) C(14) -2(2)
C(12) C(13) C(14) C(15) 1(3)
C(13) C(14) C(15) C(16) -1(3)
C(14) C(15) C(16) C(11) 1(2)
C(12) C(11) C(16) C(15) -2(2)
S(1) C(11) C(16) C(15) 178.7(11)
O(3) Si(3) C(31) C(33) -173.4(12)
C(35) Si(3) C(31) C(33) 67.0(14)
C(36) Si(3) C(31) C(33) -56.5(14)
O(3) Si(3) C(31) C(34) -54.0(13)
C(35) Si(3) C(31) C(34) -173.5(10)
C(36) Si(3) C(31) C(34) 63.0(13)
O(3) Si(3) C(31) C(32) 57.9(10)
C(35) Si(3) C(31) C(32) -61.7(11)
C(36) Si(3) C(31) C(32) 174.8(9)
O(5) Si(5) C(51) C(54) 168.6(11)
C(55) Si(5) C(51) C(54) -59.8(16)
C(56) Si(5) C(51) C(54) 57.2(14)
O(5) Si(5) C(51) C(53) -67.8(13)
C(55) Si(5) C(51) C(53) 63.8(14)
C(56) Si(5) C(51) C(53) -179.2(12)
O(5) Si(5) C(51) C(52) 55.0(11)
C(55) Si(5) C(51) C(52) -173.4(11)
C(56) Si(5) C(51) C(52) -56.4(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21199805
