#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/04/4020432.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_4020432
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_absolute_configuration rmad
_chemical_formula_sum            'C27 H29 N O3'
_chemical_formula_weight         415.51
_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                 91.3850(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.9502(2)
_cell_length_b                   9.0380(2)
_cell_length_c                   11.4961(2)
_cell_measurement_temperature    100(2)
_cell_volume                     1137.41(4)
_diffrn_ambient_temperature      100(2)
_exptl_crystal_density_diffrn    1.213
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 (34 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4020432
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
O1 O 1.19242(15) 0.4333(2) 0.87154(16) 0.0348(4) Uani 1 1 d . . .
O2 O 1.12720(17) 0.3198(2) 0.70924(16) 0.0391(4) Uani 1 1 d . . .
O3 O 0.94568(15) 0.2905(2) 0.97630(17) 0.0313(4) Uani 1 1 d . . .
H3 H 0.8823 0.2639 1.0104 0.047 Uiso 1 1 calc R . .
N1 N 0.74524(16) 0.4138(2) 1.04735(15) 0.0215(4) Uani 1 1 d . . .
C1 C 1.1098(2) 0.4020(3) 0.8062(2) 0.0290(5) Uani 1 1 d . . .
C2 C 0.9764(2) 0.4451(3) 0.8131(2) 0.0346(6) Uani 1 1 d . . .
H2 H 0.9657 0.5480 0.7825 0.041 Uiso 1 1 calc R . .
C3 C 0.9144(3) 0.3366(6) 0.7282(3) 0.0665(13) Uani 1 1 d . . .
H3A H 0.8884 0.2456 0.7686 0.080 Uiso 1 1 calc R . .
H3B H 0.8424 0.3822 0.6887 0.080 Uiso 1 1 calc R . .
C4 C 1.0131(3) 0.3038(6) 0.6432(3) 0.0589(10) Uani 1 1 d . . .
H4A H 1.0045 0.2020 0.6122 0.071 Uiso 1 1 calc R . .
H4B H 1.0095 0.3744 0.5773 0.071 Uiso 1 1 calc R . .
C5 C 0.93126(19) 0.4389(3) 0.93646(18) 0.0218(4) Uani 1 1 d . . .
H5 H 0.9823 0.5060 0.9868 0.026 Uiso 1 1 calc R . .
C6 C 0.79547(19) 0.4850(2) 0.94383(18) 0.0214(5) Uani 1 1 d . . .
H6 H 0.7521 0.4405 0.8747 0.026 Uiso 1 1 calc R . .
C7 C 0.7749(2) 0.6538(3) 0.93645(18) 0.0241(5) Uani 1 1 d . . .
H7A H 0.6977 0.6782 0.9753 0.029 Uiso 1 1 calc R . .
H7B H 0.8421 0.7042 0.9798 0.029 Uiso 1 1 calc R . .
C8 C 0.7686(2) 0.7140(3) 0.8132(2) 0.0257(5) Uani 1 1 d . . .
C9 C 0.8616(2) 0.8018(3) 0.7705(2) 0.0301(5) Uani 1 1 d . . .
H9 H 0.9304 0.8247 0.8192 0.036 Uiso 1 1 calc R . .
C10 C 0.8554(3) 0.8563(3) 0.6582(2) 0.0410(6) Uani 1 1 d . . .
H10 H 0.9201 0.9154 0.6303 0.049 Uiso 1 1 calc R . .
C11 C 0.7554(3) 0.8254(3) 0.5858(2) 0.0432(7) Uani 1 1 d . . .
H11 H 0.7517 0.8623 0.5084 0.052 Uiso 1 1 calc R . .
C12 C 0.6613(3) 0.7402(3) 0.6277(2) 0.0397(7) Uani 1 1 d . . .
H12 H 0.5918 0.7201 0.5792 0.048 Uiso 1 1 calc R . .
C13 C 0.6676(2) 0.6836(3) 0.7405(2) 0.0306(5) Uani 1 1 d . . .
H13 H 0.6028 0.6241 0.7680 0.037 Uiso 1 1 calc R . .
C14 C 0.7801(2) 0.4923(3) 1.15594(19) 0.0250(5) Uani 1 1 d . . .
H14A H 0.7314 0.5843 1.1611 0.030 Uiso 1 1 calc R . .
H14B H 0.8673 0.5207 1.1530 0.030 Uiso 1 1 calc R . .
C15 C 0.7605(2) 0.3999(3) 1.26459(19) 0.0259(5) Uani 1 1 d . . .
C16 C 0.7580(3) 0.2468(3) 1.2619(2) 0.0350(6) Uani 1 1 d . . .
H16 H 0.7689 0.1967 1.1903 0.042 Uiso 1 1 calc R . .
C17 C 0.7397(3) 0.1647(3) 1.3631(2) 0.0406(7) Uani 1 1 d . . .
H17 H 0.7390 0.0596 1.3602 0.049 Uiso 1 1 calc R . .
C18 C 0.7224(3) 0.2375(3) 1.4681(2) 0.0375(6) Uani 1 1 d . . .
H18 H 0.7098 0.1826 1.5372 0.045 Uiso 1 1 calc R . .
C19 C 0.7237(3) 0.3901(3) 1.4709(2) 0.0340(6) Uani 1 1 d . . .
H19 H 0.7110 0.4403 1.5422 0.041 Uiso 1 1 calc R . .
C20 C 0.7434(2) 0.4711(3) 1.3701(2) 0.0298(5) Uani 1 1 d . . .
H20 H 0.7452 0.5761 1.3734 0.036 Uiso 1 1 calc R . .
C21 C 0.6117(2) 0.3921(3) 1.0373(2) 0.0258(5) Uani 1 1 d . . .
H21A H 0.5708 0.4895 1.0300 0.031 Uiso 1 1 calc R . .
H21B H 0.5825 0.3435 1.1086 0.031 Uiso 1 1 calc R . .
C22 C 0.57810(19) 0.2975(3) 0.93207(19) 0.0234(4) Uani 1 1 d . . .
C23 C 0.63965(19) 0.1655(3) 0.91060(19) 0.0240(5) Uani 1 1 d . . .
H23 H 0.6987 0.1297 0.9656 0.029 Uiso 1 1 calc R . .
C24 C 0.6149(2) 0.0858(3) 0.8090(2) 0.0280(5) Uani 1 1 d . . .
H24 H 0.6587 -0.0026 0.7939 0.034 Uiso 1 1 calc R . .
C25 C 0.5269(2) 0.1349(3) 0.7303(2) 0.0308(5) Uani 1 1 d . . .
H25 H 0.5112 0.0814 0.6604 0.037 Uiso 1 1 calc R . .
C26 C 0.4612(2) 0.2628(3) 0.7533(2) 0.0333(6) Uani 1 1 d . . .
H26 H 0.3982 0.2945 0.7007 0.040 Uiso 1 1 calc R . .
C27 C 0.4879(2) 0.3444(3) 0.8535(2) 0.0294(5) Uani 1 1 d . . .
H27 H 0.4441 0.4329 0.8683 0.035 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 C1 . . 1.195(3) y
O2 C1 . . 1.357(3) y
O2 C4 . . 1.454(4) y
O3 C5 . . 1.424(3) y
O3 H3 . . 0.84 ?
N1 C6 . . 1.471(3) y
N1 C21 . . 1.477(3) y
N1 C14 . . 1.478(3) y
C1 C2 . . 1.517(3) y
C2 C5 . . 1.514(3) y
C2 C3 . . 1.531(5) y
C2 H2 . . 1 ?
C3 C4 . . 1.504(4) y
C3 H3a . . 0.99 ?
C3 H3b . . 0.99 ?
C4 H4a . . 0.99 ?
C4 H4b . . 0.99 ?
C5 C6 . . 1.549(3) y
C5 H5 . . 1 ?
C6 C7 . . 1.544(3) y
C6 H6 . . 1 ?
C7 C8 . . 1.517(3) y
C7 H7a . . 0.99 ?
C7 H7b . . 0.99 ?
C8 C9 . . 1.391(4) y
C8 C13 . . 1.398(3) y
C9 C10 . . 1.382(4) y
C9 H9 . . 0.95 ?
C10 C11 . . 1.387(4) y
C10 H10 . . 0.95 ?
C11 C12 . . 1.382(5) y
C11 H11 . . 0.95 ?
C12 C13 . . 1.394(4) y
C12 H12 . . 0.95 ?
C13 H13 . . 0.95 ?
C14 C15 . . 1.522(3) y
C14 H14a . . 0.99 ?
C14 H14b . . 0.99 ?
C15 C16 . . 1.384(4) y
C15 C20 . . 1.389(3) y
C16 C17 . . 1.398(4) y
C16 H16 . . 0.95 ?
C17 C18 . . 1.392(4) y
C17 H17 . . 0.95 ?
C18 C19 . . 1.380(4) y
C18 H18 . . 0.95 ?
C19 C20 . . 1.392(4) y
C19 H19 . . 0.95 ?
C20 H20 . . 0.95 ?
C21 C22 . . 1.519(3) y
C21 H21a . . 0.99 ?
C21 H21b . . 0.99 ?
C22 C27 . . 1.388(3) y
C22 C23 . . 1.396(3) y
C23 C24 . . 1.393(3) y
C23 H23 . . 0.95 ?
C24 C25 . . 1.379(4) y
C24 H24 . . 0.95 ?
C25 C26 . . 1.390(4) y
C25 H25 . . 0.95 ?
C26 C27 . . 1.394(4) y
C26 H26 . . 0.95 ?
C27 H27 . . 0.95 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9329351
