#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/07/4020795.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_4020795
loop_
_publ_author_name
'Shawn R. Hitchcock'
'David M. Casper'
'Jeremy F. Vaughn'
'Jennifer M. Finefield'
'Gregory M. Ferrence'
'Joel M. Esken'
_publ_section_title
;
 Intramolecular Chiral Relay at Stereogenic Nitrogen.
 Synthesis and Application of a New Chiral Auxiliary
 Derived from (1R,2S)-Norephedrine and Acetone
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              714
_journal_page_last               718
_journal_paper_doi               10.1021/jo035325n
_journal_volume                  69
_journal_year                    2004
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H26 N2 O3 S1'
_chemical_formula_sum            'C22 H26 N2 O3 S'
_chemical_formula_weight         398.51
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6661(6)
_cell_length_b                   9.9694(6)
_cell_length_c                   21.1650(14)
_cell_measurement_temperature    193(2)
_cell_measurement_wavelength     0.71073
_cell_volume                     2039.6(2)
_diffrn_ambient_temperature      193(2)
_exptl_crystal_density_diffrn    1.298
_cod_database_code               4020795
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
C2 C 0.67462(13) 0.10057(12) 0.33671(6) 0.0297(3) Uani 1 1 d . . .
C5 C 0.43532(12) -0.04948(12) 0.32499(6) 0.0262(2) Uani 1 1 d . . .
H5 H 0.3441 -0.0815 0.3086 0.031 Uiso 1 1 calc R . .
C6 C 0.41865(12) 0.09674(12) 0.34542(6) 0.0257(2) Uani 1 1 d . . .
H6 H 0.3795 0.1482 0.309 0.031 Uiso 1 1 calc R . .
C7 C 0.32531(13) 0.11728(11) 0.40149(6) 0.0266(2) Uani 1 1 d . . .
C8 C 0.37146(14) 0.10992(13) 0.46382(6) 0.0328(3) Uani 1 1 d . . .
H8 H 0.4671 0.0971 0.4723 0.039 Uiso 1 1 calc R . .
C9 C 0.27876(17) 0.12114(15) 0.51354(7) 0.0388(3) Uani 1 1 d . . .
H9 H 0.3111 0.1165 0.5559 0.047 Uiso 1 1 calc R . .
C10 C 0.13857(16) 0.13910(14) 0.50162(7) 0.0397(3) Uani 1 1 d . . .
H10 H 0.0749 0.1451 0.5357 0.048 Uiso 1 1 calc R . .
C11 C 0.09193(14) 0.14829(14) 0.43986(7) 0.0370(3) Uani 1 1 d . . .
H11 H -0.0038 0.1612 0.4316 0.044 Uiso 1 1 calc R . .
C12 C 0.18453(13) 0.13864(12) 0.39009(6) 0.0308(3) Uani 1 1 d . . .
H12 H 0.1521 0.1466 0.3479 0.037 Uiso 1 1 calc R . .
C13 C 0.48023(15) -0.14332(13) 0.37784(6) 0.0341(3) Uani 1 1 d . . .
H13A H 0.5154 -0.227 0.3596 0.041 Uiso 1 1 calc R . .
H13B H 0.4009 -0.163 0.4051 0.041 Uiso 1 1 calc R . .
H13C H 0.5533 -0.1004 0.4028 0.041 Uiso 1 1 calc R . .
C14 C 0.50106(14) 0.02645(13) 0.21571(6) 0.0308(3) Uani 1 1 d . . .
H14 H 0.5014 0.1238 0.2272 0.037 Uiso 1 1 calc R . .
C15 C 0.35876(16) -0.01204(16) 0.19165(7) 0.0430(3) Uani 1 1 d . . .
H15A H 0.3533 -0.1097 0.1871 0.052 Uiso 1 1 calc R . .
H15B H 0.3426 0.0304 0.1505 0.052 Uiso 1 1 calc R . .
H15C H 0.2884 0.0184 0.2217 0.052 Uiso 1 1 calc R . .
C16 C 0.60874(17) 0.00131(16) 0.16502(6) 0.0437(4) Uani 1 1 d . . .
H16A H 0.6993 0.0321 0.18 0.052 Uiso 1 1 calc R . .
H16B H 0.5835 0.0505 0.1266 0.052 Uiso 1 1 calc R . .
H16C H 0.613 -0.0949 0.1557 0.052 Uiso 1 1 calc R . .
C17 C 0.77713(13) -0.10348(13) 0.28670(6) 0.0278(3) Uani 1 1 d . . .
C19 C 0.91912(13) -0.06990(13) 0.31200(6) 0.0309(3) Uani 1 1 d . . .
H19A H 0.9118 -0.0453 0.3572 0.037 Uiso 1 1 calc R . .
H19B H 0.9567 0.0083 0.2888 0.037 Uiso 1 1 calc R . .
C20 C 1.01733(13) -0.18849(14) 0.30480(7) 0.0369(3) Uani 1 1 d . . .
H20A H 1.1103 -0.1616 0.3198 0.044 Uiso 1 1 calc R . .
H20B H 1.0252 -0.2113 0.2594 0.044 Uiso 1 1 calc R . .
C22 C 1.08189(13) -0.34842(14) 0.41144(7) 0.0345(3) Uani 1 1 d . . .
C23 C 1.12456(15) -0.47671(15) 0.42888(7) 0.0399(3) Uani 1 1 d . . .
H23 H 1.0902 -0.5528 0.4069 0.048 Uiso 1 1 calc R . .
C24 C 1.21681(17) -0.49332(19) 0.47815(8) 0.0512(4) Uani 1 1 d . . .
H24 H 1.2452 -0.581 0.49 0.061 Uiso 1 1 calc R . .
C25 C 1.26753(18) -0.3845(2) 0.50991(8) 0.0541(5) Uani 1 1 d . . .
H25 H 1.3331 -0.3965 0.5429 0.065 Uiso 1 1 calc R . .
C26 C 1.22346(18) -0.2569(2) 0.49408(8) 0.0497(4) Uani 1 1 d . . .
H26 H 1.2573 -0.1816 0.5168 0.06 Uiso 1 1 calc R . .
C27 C 1.13023(16) -0.23865(15) 0.44520(8) 0.0424(3) Uani 1 1 d . . .
H27 H 1.0993 -0.151 0.4348 0.051 Uiso 1 1 calc R . .
N3 N 0.66646(10) -0.01292(10) 0.29761(5) 0.0258(2) Uani 1 1 d . . .
N4 N 0.53557(10) -0.05489(10) 0.27280(5) 0.0242(2) Uani 1 1 d . . .
O1 O 0.55611(9) 0.15076(8) 0.35944(4) 0.02994(19) Uani 1 1 d . . .
O18 O 0.75694(10) -0.20426(10) 0.25662(5) 0.0367(2) Uani 1 1 d . . .
O28 O 0.78155(10) 0.15346(11) 0.35110(6) 0.0454(3) Uani 1 1 d . . .
S21 S 0.96222(4) -0.33729(4) 0.34812(2) 0.04670(11) Uani 1 1 d . . .
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
C2 O28 1.1996(16) . ?
C2 O1 1.3394(15) . ?
C2 N3 1.4040(16) . ?
C5 N4 1.4703(15) . ?
C5 C13 1.5215(17) . ?
C5 C6 1.5290(16) . ?
C6 O1 1.4642(14) . ?
C6 C7 1.5047(17) . ?
C7 C8 1.3946(18) . ?
C7 C12 1.3983(18) . ?
C8 C9 1.387(2) . ?
C9 C10 1.390(2) . ?
C10 C11 1.386(2) . ?
C11 C12 1.3856(19) . ?
C14 N4 1.4929(15) . ?
C14 C16 1.5157(19) . ?
C14 C15 1.516(2) . ?
C17 O18 1.2053(15) . ?
C17 N3 1.4187(16) . ?
C17 C19 1.5108(17) . ?
C19 C20 1.5238(19) . ?
C20 S21 1.8236(15) . ?
C22 C27 1.388(2) . ?
C22 C23 1.394(2) . ?
C22 S21 1.7737(14) . ?
C23 C24 1.382(2) . ?
C24 C25 1.368(3) . ?
C25 C26 1.382(3) . ?
C26 C27 1.384(2) . ?
N3 N4 1.4324(14) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21176787
2 PubChem 101337219
