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#$Date: 2016-03-21 02:20:25 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178382 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/04/4020433.cif $
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#
# 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_4020433
loop_
_publ_author_name
'Stephen Hanessian'
'Yihua Hou'
'Malken Bayrakdarian'
'Marina Tintelnot-Blomley'
_publ_section_title
;
 Stereoselective Synthesis of Constrained Oxacyclic Hydroxyethylene
 Isosteres of Aspartic Protease Inhibitors: Aldol and Mukaiyama Aldol
 Methodologies for Branched Tetrahydrofuran 2-Carboxylic Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6735
_journal_page_last               6745
_journal_paper_doi               10.1021/jo050749y
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C30 H45 N O3 Si'
_chemical_formula_weight         495.76
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 111.00(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.445(3)
_cell_length_b                   10.280(3)
_cell_length_c                   12.701(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1517.0(7)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.085
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4020433
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4462(4) 0.3964(6) 0.5329(3) 0.1063(13) Uani 1 1 d . . .
O1 O 0.5236(2) 0.3212(4) 0.5698(2) 0.1332(11) Uani 1 1 d . . .
C2 C 0.3380(3) 0.3790(4) 0.4285(3) 0.0899(10) Uani 1 1 d . . .
H2 H 0.3586 0.3981 0.3625 0.108 Uiso 1 1 calc R . .
C3 C 0.2609(3) 0.4881(4) 0.4397(3) 0.1077(12) Uani 1 1 d . . .
H3A H 0.2187 0.5264 0.3667 0.129 Uiso 1 1 calc R . .
H3B H 0.2066 0.4566 0.4726 0.129 Uiso 1 1 calc R . .
C4 C 0.3421(4) 0.5849(5) 0.5158(4) 0.1498(17) Uani 1 1 d . . .
H4A H 0.3598 0.6534 0.4720 0.180 Uiso 1 1 calc R . .
H4B H 0.3086 0.6238 0.5665 0.180 Uiso 1 1 calc R . .
O4 O 0.4449(3) 0.5126(4) 0.5787(3) 0.1358(10) Uani 1 1 d . . .
C5 C 0.2882(3) 0.2431(4) 0.4138(2) 0.0890(10) Uani 1 1 d . A .
H5 H 0.3499 0.1793 0.4250 0.107 Uiso 1 1 calc R . .
O5 O 0.23406(16) 0.2211(3) 0.49442(17) 0.0995(7) Uani 1 1 d D . .
C6 C 0.1968(3) 0.2275(4) 0.2941(2) 0.0861(9) Uani 1 1 d . . .
H6 H 0.1477 0.3049 0.2795 0.103 Uiso 1 1 calc R A .
N6 N 0.2599(2) 0.2321(3) 0.2140(2) 0.0851(8) Uani 1 1 d . A .
C7 C 0.1190(3) 0.1106(4) 0.2844(3) 0.1148(13) Uani 1 1 d D A .
H7A H 0.1639 0.0340 0.2830 0.138 Uiso 0.768(3) 1 calc PR A -1
H7B H 0.1033 0.1066 0.3538 0.138 Uiso 0.768(3) 1 calc PR A -1
H7C H 0.1169 0.0619 0.2183 0.138 Uiso 0.232(3) 1 calc PR A -2
H7D H 0.1560 0.0555 0.3493 0.138 Uiso 0.232(3) 1 calc PR A -2
C8 C 0.0091(4) 0.0970(6) 0.1923(4) 0.1053(16) Uani 0.768(3) 1 d PD A -1
H8 H 0.0279 0.0922 0.1238 0.126 Uiso 0.768(3) 1 calc PR A -1
C9 C -0.0730(12) 0.2073(10) 0.1734(8) 0.132(3) Uani 0.768(3) 1 d PD A -1
H9A H -0.1378 0.1928 0.1052 0.198 Uiso 0.768(3) 1 calc PR A -1
H9B H -0.0353 0.2867 0.1671 0.198 Uiso 0.768(3) 1 calc PR A -1
H9C H -0.0991 0.2134 0.2359 0.198 Uiso 0.768(3) 1 calc PR A -1
C10 C -0.0489(7) -0.0312(7) 0.1976(5) 0.131(2) Uani 0.768(3) 1 d PD A -1
H10A H 0.0057 -0.1008 0.2095 0.197 Uiso 0.768(3) 1 calc PR A -1
H10B H -0.1120 -0.0451 0.1279 0.197 Uiso 0.768(3) 1 calc PR A -1
H10C H -0.0772 -0.0290 0.2587 0.197 Uiso 0.768(3) 1 calc PR A -1
C8' C 0.0009(11) 0.1297(16) 0.2766(16) 0.1053(16) Uani 0.23 1 d PD A -2
H8' H 0.0068 0.1541 0.3531 0.126 Uiso 0.232(3) 1 calc PR A -2
C9' C -0.072(4) 0.233(3) 0.203(4) 0.132(3) Uani 0.23 1 d PD A -2
H9'1 H -0.1360 0.2505 0.2256 0.198 Uiso 0.232(3) 1 calc PR A -2
H9'2 H -0.0987 0.2041 0.1262 0.198 Uiso 0.232(3) 1 calc PR A -2
H9'3 H -0.0267 0.3105 0.2104 0.198 Uiso 0.232(3) 1 calc PR A -2
C10' C -0.063(3) 0.001(2) 0.255(2) 0.131(2) Uani 0.23 1 d PD A -2
H10D H -0.0158 -0.0641 0.3040 0.197 Uiso 0.232(3) 1 calc PR A -2
H10E H -0.0799 -0.0242 0.1778 0.197 Uiso 0.232(3) 1 calc PR A -2
H10F H -0.1333 0.0104 0.2689 0.197 Uiso 0.232(3) 1 calc PR A -2
C11 C 0.3037(3) 0.1057(4) 0.1950(3) 0.0981(11) Uani 1 1 d . . .
H11A H 0.2413 0.0568 0.1413 0.118 Uiso 1 1 calc R A .
H11B H 0.3302 0.0575 0.2653 0.118 Uiso 1 1 calc R . .
C12 C 0.4008(3) 0.1164(4) 0.1512(3) 0.0945(11) Uani 1 1 d . A .
C13 C 0.4074(4) 0.0317(5) 0.0698(3) 0.1254(15) Uani 1 1 d . . .
H13 H 0.3494 -0.0291 0.0386 0.151 Uiso 1 1 calc R A .
C14 C 0.5000(5) 0.0369(6) 0.0345(4) 0.1485(19) Uani 1 1 d . A .
H14 H 0.5035 -0.0207 -0.0207 0.178 Uiso 1 1 calc R . .
C15 C 0.5863(4) 0.1244(6) 0.0787(4) 0.1388(17) Uani 1 1 d . . .
H15 H 0.6478 0.1271 0.0535 0.167 Uiso 1 1 calc R A .
C16 C 0.5818(3) 0.2072(5) 0.1594(4) 0.1211(14) Uani 1 1 d . A .
H16 H 0.6410 0.2666 0.1911 0.145 Uiso 1 1 calc R . .
C17 C 0.4888(3) 0.2035(4) 0.1949(3) 0.1070(12) Uani 1 1 d . . .
H17 H 0.4861 0.2617 0.2499 0.128 Uiso 1 1 calc R A .
C18 C 0.1979(3) 0.3022(4) 0.1077(3) 0.0983(11) Uani 1 1 d . . .
H18A H 0.1201 0.2686 0.0755 0.118 Uiso 1 1 calc R A .
H18B H 0.2359 0.2856 0.0544 0.118 Uiso 1 1 calc R . .
C19 C 0.1929(4) 0.4445(4) 0.1238(3) 0.0897(10) Uani 1 1 d . A .
C20 C 0.2914(3) 0.5183(5) 0.1544(3) 0.0962(11) Uani 1 1 d . . .
H20 H 0.3609 0.4783 0.1624 0.115 Uiso 1 1 calc R A .
C21 C 0.2895(4) 0.6483(6) 0.1732(3) 0.1234(14) Uani 1 1 d . A .
H21 H 0.3575 0.6960 0.1941 0.148 Uiso 1 1 calc R . .
C22 C 0.1872(6) 0.7096(5) 0.1614(3) 0.1355(16) Uani 1 1 d . . .
H22 H 0.1860 0.7985 0.1745 0.163 Uiso 1 1 calc R A .
C23 C 0.0880(4) 0.6391(6) 0.1304(4) 0.1234(15) Uani 1 1 d . A .
H23 H 0.0188 0.6797 0.1225 0.148 Uiso 1 1 calc R . .
C24 C 0.0904(3) 0.5088(5) 0.1108(3) 0.1047(12) Uani 1 1 d . . .
H24 H 0.0220 0.4618 0.0882 0.126 Uiso 1 1 calc R A .
Si Si 0.28316(13) 0.16179(18) 0.62498(12) 0.0878(5) Uani 0.768(3) 1 d PD A -1
C25 C 0.3422(5) 0.2903(6) 0.7336(4) 0.1282(19) Uani 0.768(3) 1 d PD A -1
H25A H 0.4112 0.3254 0.7274 0.192 Uiso 0.768(3) 1 calc PR A -1
H25B H 0.3595 0.2534 0.8073 0.192 Uiso 0.768(3) 1 calc PR A -1
H25C H 0.2864 0.3584 0.7222 0.192 Uiso 0.768(3) 1 calc PR A -1
C26 C 0.3936(5) 0.0320(7) 0.6315(8) 0.117(3) Uani 0.768(3) 1 d PD A -1
H26A H 0.3598 -0.0315 0.5735 0.175 Uiso 0.768(3) 1 calc PR A -1
H26B H 0.4182 -0.0097 0.7039 0.175 Uiso 0.768(3) 1 calc PR A -1
H26C H 0.4586 0.0713 0.6202 0.175 Uiso 0.768(3) 1 calc PR A -1
C27 C 0.1541(5) 0.0789(5) 0.6430(5) 0.0902(17) Uani 0.768(3) 1 d PD A -1
C28 C 0.0531(7) 0.1812(16) 0.6045(13) 0.135(4) Uani 0.768(3) 1 d PD A -1
H28A H 0.0262 0.1909 0.5241 0.203 Uiso 0.768(3) 1 calc PR A -1
H28B H 0.0804 0.2636 0.6396 0.203 Uiso 0.768(3) 1 calc PR A -1
H28C H -0.0090 0.1516 0.6266 0.203 Uiso 0.768(3) 1 calc PR A -1
C29 C 0.1857(16) 0.0602(11) 0.7740(10) 0.143(4) Uani 0.768(3) 1 d PD A -1
H29A H 0.1934 0.1438 0.8097 0.215 Uiso 0.768(3) 1 calc PR A -1
H29B H 0.2570 0.0136 0.8047 0.215 Uiso 0.768(3) 1 calc PR A -1
H29C H 0.1258 0.0118 0.7873 0.215 Uiso 0.768(3) 1 calc PR A -1
C30 C 0.1230(5) -0.0449(6) 0.5806(5) 0.1320(19) Uani 0.768(3) 1 d PD A -1
H30A H 0.0586 -0.0830 0.5939 0.198 Uiso 0.768(3) 1 calc PR A -1
H30B H 0.1873 -0.1034 0.6059 0.198 Uiso 0.768(3) 1 calc PR A -1
H30C H 0.1027 -0.0287 0.5014 0.198 Uiso 0.768(3) 1 calc PR A -1
Si' Si 0.2585(5) 0.0822(6) 0.5737(5) 0.107(2) Uani 0.232(3) 1 d PD A -2
C25' C 0.2058(15) -0.0807(15) 0.5099(13) 0.1282(19) Uani 0.23 1 d PD A -2
H25A H 0.1343 -0.0703 0.4478 0.192 Uiso 0.232(3) 1 calc PR A -2
H25B H 0.1943 -0.1362 0.5657 0.192 Uiso 0.232(3) 1 calc PR A -2
H25C H 0.2618 -0.1191 0.4834 0.192 Uiso 0.232(3) 1 calc PR A -2
C26' C 0.4168(14) 0.084(3) 0.657(3) 0.117(3) Uani 0.23 1 d PD A -2
H26D H 0.4582 0.0965 0.6070 0.175 Uiso 0.232(3) 1 calc PR A -2
H26E H 0.4390 0.0025 0.6958 0.175 Uiso 0.232(3) 1 calc PR A -2
H26F H 0.4342 0.1535 0.7109 0.175 Uiso 0.232(3) 1 calc PR A -2
C27' C 0.1771(17) 0.135(2) 0.6654(19) 0.0902(17) Uani 0.23 1 d PD A -2
C28' C 0.047(2) 0.149(7) 0.589(4) 0.135(4) Uani 0.23 1 d PD A -2
H28D H 0.0344 0.1119 0.5166 0.203 Uiso 0.232(3) 1 calc PR A -2
H28E H 0.0264 0.2392 0.5813 0.203 Uiso 0.232(3) 1 calc PR A -2
H28F H 0.0005 0.1039 0.6240 0.203 Uiso 0.232(3) 1 calc PR A -2
C29' C 0.182(6) 0.025(4) 0.755(4) 0.143(4) Uani 0.23 1 d PD A -2
H29D H 0.1597 0.0616 0.8138 0.215 Uiso 0.232(3) 1 calc PR A -2
H29E H 0.2591 -0.0080 0.7871 0.215 Uiso 0.232(3) 1 calc PR A -2
H29F H 0.1305 -0.0441 0.7187 0.215 Uiso 0.232(3) 1 calc PR A -2
C30' C 0.2375(17) 0.2476(17) 0.7323(14) 0.1320(19) Uani 0.23 1 d PD A -2
H30D H 0.1920 0.3245 0.7062 0.198 Uiso 0.232(3) 1 calc PR A -2
H30E H 0.3106 0.2582 0.7240 0.198 Uiso 0.232(3) 1 calc PR A -2
H30F H 0.2491 0.2335 0.8104 0.198 Uiso 0.232(3) 1 calc PR A -2
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
C1 O1 1.192(5) . ?
C1 O4 1.331(5) . ?
C1 C2 1.524(5) . ?
C2 C5 1.512(5) . ?
C2 C3 1.515(5) . ?
C2 H2 0.9800 . ?
C3 C4 1.499(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O4 1.448(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O5 1.432(3) . ?
C5 C6 1.546(4) . ?
C5 H5 0.9800 . ?
O5 Si 1.664(2) . ?
O5 Si' 1.711(4) . ?
C6 N6 1.491(4) . ?
C6 C7 1.520(4) . ?
C6 H6 0.9800 . ?
N6 C11 1.463(4) . ?
N6 C18 1.481(4) . ?
C7 C8' 1.451(13) . ?
C7 C8 1.453(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C7 H7D 0.9700 . ?
C8 C9 1.487(9) . ?
C8 C10 1.516(7) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C8' C9' 1.484(17) . ?
C8' C10' 1.514(16) . ?
C8' H8' 0.9800 . ?
C9' H9'1 0.9600 . ?
C9' H9'2 0.9600 . ?
C9' H9'3 0.9600 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
C11 C12 1.505(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C17 1.368(5) . ?
C12 C13 1.377(5) . ?
C13 C14 1.380(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.358(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.349(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.481(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.374(5) . ?
C19 C24 1.393(5) . ?
C20 C21 1.359(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.363(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.365(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
Si C25 1.861(5) . ?
Si C26 1.896(6) . ?
Si C27 1.903(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C30 1.476(7) . ?
C27 C28 1.577(10) . ?
C27 C29 1.579(9) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
Si' C26' 1.872(15) . ?
Si' C25' 1.874(13) . ?
Si' C27' 1.877(14) . ?
C25' H25A 0.9600 . ?
C25' H25B 0.9600 . ?
C25' H25C 0.9600 . ?
C26' H26D 0.9600 . ?
C26' H26E 0.9600 . ?
C26' H26F 0.9600 . ?
C27' C30' 1.475(16) . ?
C27' C28' 1.566(17) . ?
C27' C29' 1.586(17) . ?
C28' H28D 0.9600 . ?
C28' H28E 0.9600 . ?
C28' H28F 0.9600 . ?
C29' H29D 0.9600 . ?
C29' H29E 0.9600 . ?
C29' H29F 0.9600 . ?
C30' H30D 0.9600 . ?
C30' H30E 0.9600 . ?
C30' H30F 0.9600 . ?
