#------------------------------------------------------------------------------
#$Date: 2022-09-14 21:32:59 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/04/4020431.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_4020431
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            'C21 H25 N O3'
_chemical_formula_weight         339.42
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.781(3)
_cell_length_b                   24.480(11)
_cell_length_c                   10.034(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1911.3(14)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_meas      ?
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (27 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4020431
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
'-x, -y, 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
O1 O 0.7489(3) 0.50032(8) 0.02641(18) 0.1087(7) Uani 1 1 d . . .
O2 O 0.7822(3) 0.47257(7) 0.23301(19) 0.0984(6) Uani 1 1 d . . .
O3 O 0.9679(3) 0.60425(7) 0.1641(2) 0.0934(6) Uani 1 1 d . . .
H3 H 1.0531 0.5865 0.1851 0.140 Uiso 1 1 calc R . .
N N 0.6268(3) 0.64528(8) 0.40100(18) 0.0759(6) Uani 1 1 d . . .
C2 C 0.7434(4) 0.50854(11) 0.1574(3) 0.0790(7) Uani 1 1 d . . .
C3 C 0.6888(3) 0.56525(9) 0.1902(2) 0.0715(6) Uani 1 1 d . . .
H3A H 0.5890 0.5639 0.2496 0.086 Uiso 1 1 calc R . .
C4 C 0.6335(4) 0.58857(11) 0.0551(2) 0.0921(9) Uani 1 1 d . . .
H4A H 0.5092 0.5899 0.0479 0.111 Uiso 1 1 calc R . .
H4B H 0.6792 0.6251 0.0422 0.111 Uiso 1 1 calc R . .
C5 C 0.7075(6) 0.54980(12) -0.0437(3) 0.1249(13) Uani 1 1 d . . .
H5A H 0.6249 0.5424 -0.1138 0.150 Uiso 1 1 calc R . .
H5B H 0.8101 0.5652 -0.0837 0.150 Uiso 1 1 calc R . .
C6 C 0.8338(3) 0.59495(9) 0.2594(2) 0.0731(6) Uani 1 1 d . . .
H6 H 0.8785 0.5716 0.3308 0.088 Uiso 1 1 calc R . .
C7 C 0.7829(3) 0.65004(10) 0.3186(3) 0.0795(7) Uani 1 1 d . . .
H7 H 0.7526 0.6736 0.2432 0.095 Uiso 1 1 calc R . .
C8 C 0.9374(5) 0.67699(14) 0.3871(4) 0.1260(12) Uani 1 1 d . . .
H8A H 0.8993 0.7082 0.4368 0.189 Uiso 1 1 calc R . .
H8B H 1.0191 0.6883 0.3210 0.189 Uiso 1 1 calc R . .
H8C H 0.9905 0.6513 0.4465 0.189 Uiso 1 1 calc R . .
C9 C 0.5426(4) 0.69835(10) 0.4180(3) 0.0887(8) Uani 1 1 d . . .
H9A H 0.6260 0.7245 0.4512 0.106 Uiso 1 1 calc R . .
H9B H 0.4525 0.6949 0.4843 0.106 Uiso 1 1 calc R . .
C10 C 0.4661(4) 0.71981(10) 0.2911(2) 0.0769(7) Uani 1 1 d . . .
C11 C 0.4965(4) 0.77229(10) 0.2482(3) 0.0925(8) Uani 1 1 d . . .
H11 H 0.5701 0.7948 0.2962 0.111 Uiso 1 1 calc R . .
C12 C 0.4177(5) 0.79175(14) 0.1334(3) 0.1096(11) Uani 1 1 d . . .
H12 H 0.4396 0.8271 0.1043 0.131 Uiso 1 1 calc R . .
C13 C 0.3081(6) 0.75904(15) 0.0635(4) 0.1197(12) Uani 1 1 d . . .
H13 H 0.2551 0.7722 -0.0132 0.144 Uiso 1 1 calc R . .
C14 C 0.2762(5) 0.70727(14) 0.1055(3) 0.1146(11) Uani 1 1 d . . .
H14 H 0.2011 0.6851 0.0578 0.138 Uiso 1 1 calc R . .
C15 C 0.3542(4) 0.68771(11) 0.2177(3) 0.0937(8) Uani 1 1 d . . .
H15 H 0.3317 0.6522 0.2453 0.112 Uiso 1 1 calc R . .
C16 C 0.6546(5) 0.61940(12) 0.5323(3) 0.0972(9) Uani 1 1 d . . .
H16A H 0.7128 0.6450 0.5905 0.117 Uiso 1 1 calc R . .
H16B H 0.7284 0.5878 0.5214 0.117 Uiso 1 1 calc R . .
C17 C 0.4901(5) 0.60201(12) 0.5957(3) 0.0952(9) Uani 1 1 d . . .
C18 C 0.4420(6) 0.62008(16) 0.7221(3) 0.1268(13) Uani 1 1 d . . .
H18 H 0.5130 0.6441 0.7681 0.152 Uiso 1 1 calc R . .
C19 C 0.2915(7) 0.6029(2) 0.7796(4) 0.1491(19) Uani 1 1 d . . .
H19 H 0.2619 0.6151 0.8643 0.179 Uiso 1 1 calc R . .
C20 C 0.1855(7) 0.56826(19) 0.7137(5) 0.1526(18) Uani 1 1 d . . .
H20 H 0.0844 0.5563 0.7536 0.183 Uiso 1 1 calc R . .
C21 C 0.2278(6) 0.55084(16) 0.5881(4) 0.1443(15) Uani 1 1 d . . .
H21 H 0.1543 0.5276 0.5419 0.173 Uiso 1 1 calc R . .
C22 C 0.3777(6) 0.56760(14) 0.5312(4) 0.1194(12) Uani 1 1 d . . .
H22 H 0.4050 0.5554 0.4460 0.143 Uiso 1 1 calc R . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . . 1.330(3) y
O1 C5 . . 1.437(3) y
O2 C2 . . 1.201(3) y
O3 C6 . . 1.433(3) y
O3 H3 . . 0.82 ?
N C9 . . 1.465(3) y
N C7 . . 1.474(3) y
N C16 . . 1.477(3) y
C2 C3 . . 1.489(3) y
C3 C6 . . 1.511(3) y
C3 C4 . . 1.533(3) y
C3 H3a . . 0.98 ?
C4 C5 . . 1.488(4) y
C4 H4a . . 0.97 ?
C4 H4b . . 0.97 ?
C5 H5a . . 0.97 ?
C5 H5b . . 0.97 ?
C6 C7 . . 1.526(3) y
C6 H6 . . 0.98 ?
C7 C8 . . 1.534(4) y
C7 H7 . . 0.98 ?
C8 H8a . . 0.96 ?
C8 H8b . . 0.96 ?
C8 H8c . . 0.96 ?
C9 C10 . . 1.501(4) y
C9 H9a . . 0.97 ?
C9 H9b . . 0.97 ?
C10 C11 . . 1.376(3) y
C10 C15 . . 1.385(4) y
C11 C12 . . 1.389(4) y
C11 H11 . . 0.93 ?
C12 C13 . . 1.364(4) y
C12 H12 . . 0.93 ?
C13 C14 . . 1.359(4) y
C13 H13 . . 0.93 ?
C14 C15 . . 1.366(4) y
C14 H14 . . 0.93 ?
C15 H15 . . 0.93 ?
C16 C17 . . 1.492(4) y
C16 H16a . . 0.97 ?
C16 H16b . . 0.97 ?
C17 C22 . . 1.376(5) y
C17 C18 . . 1.394(4) y
C18 C19 . . 1.371(6) y
C18 H18 . . 0.93 ?
C19 C20 . . 1.355(6) y
C19 H19 . . 0.93 ?
C20 C21 . . 1.370(5) y
C20 H20 . . 0.93 ?
C21 C22 . . 1.362(5) y
C21 H21 . . 0.93 ?
C22 H22 . . 0.93 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9396522
