#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/09/4020917.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_4020917
loop_
_publ_author_name
'Iwona Kudyba'
'Jerzy Raczko'
'Janusz Jurczak'
_publ_section_title
;
 Asymmetric Nitroaldol Reaction. Synthesis of Taxotere Side Chain
 and (-)-Bestatin Using (1R)-8-Phenylmenthyl Glyoxylate
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2844
_journal_page_last               2850
_journal_paper_doi               10.1021/jo0358269
_journal_volume                  69
_journal_year                    2004
_chemical_formula_sum            'C26 H33 N O5'
_chemical_formula_weight         439.53
_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                 94.61(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5610(19)
_cell_length_b                   11.203(2)
_cell_length_c                   11.353(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1212.1(4)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.204
_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.

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               4020917
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 0.26645(18) 0.87409(14) 0.19851(14) 0.0518(5) Uani 1 1 d . . .
N N -0.0572(3) 0.9226(2) 0.02023(17) 0.0605(6) Uani 1 1 d . . .
O2 O 0.08956(19) 0.93989(19) 0.29878(16) 0.0696(6) Uani 1 1 d . . .
C2 C 0.5028(3) 0.9148(3) 0.2880(2) 0.0504(7) Uani 1 1 d . . .
C13 C 0.0477(3) 0.7784(3) 0.1656(2) 0.0542(7) Uani 1 1 d . . .
O3 O -0.0769(2) 0.7641(3) 0.2211(2) 0.0863(8) Uani 1 1 d . . .
C11 C 0.1358(3) 0.8737(3) 0.2276(2) 0.0485(7) Uani 1 1 d . . .
C6 C 0.3723(4) 1.0549(3) 0.1425(3) 0.0601(8) Uani 1 1 d . . .
C14 C 0.0121(3) 0.8023(2) 0.0337(2) 0.0497(7) Uani 1 1 d . . .
C16 C 0.4155(3) 0.7130(2) 0.3524(2) 0.0557(7) Uani 1 1 d . . .
C1 C 0.3622(3) 0.9693(2) 0.2437(2) 0.0515(7) Uani 1 1 d . . .
C7 C 0.4967(3) 0.8252(3) 0.3920(2) 0.0567(8) Uani 1 1 d . . .
C15 C 0.1338(3) 0.7958(3) -0.0427(2) 0.0548(7) Uani 1 1 d . . .
C4 C 0.6133(4) 1.1069(3) 0.2167(4) 0.0732(9) Uani 1 1 d . . .
C22 C 0.0963(3) 0.8139(3) -0.1721(2) 0.0550(7) Uani 1 1 d . . .
C9 C 0.4351(4) 0.8852(4) 0.4977(3) 0.0756(10) Uani 1 1 d . . .
O4 O 0.0178(3) 1.0093(2) 0.0266(2) 0.0861(7) Uani 1 1 d . . .
C3 C 0.6022(4) 1.0202(3) 0.3174(3) 0.0710(9) Uani 1 1 d . . .
C21 C 0.4594(5) 0.6444(3) 0.2636(3) 0.0756(10) Uani 1 1 d . . .
C5 C 0.4724(3) 1.1575(3) 0.1721(3) 0.0669(8) Uani 1 1 d . . .
C23 C 0.0219(3) 0.7297(3) -0.2383(3) 0.0682(9) Uani 1 1 d . . .
C27 C 0.1395(4) 0.9138(4) -0.2280(4) 0.0752(9) Uani 1 1 d . . .
O5 O -0.1819(3) 0.9277(3) 0.0047(2) 0.1206(10) Uani 1 1 d . . .
C8 C 0.6460(3) 0.7844(4) 0.4338(4) 0.0768(10) Uani 1 1 d . . .
C19 C 0.2637(5) 0.5093(4) 0.2838(5) 0.0977(14) Uani 1 1 d . . .
C18 C 0.2239(5) 0.5754(4) 0.3722(4) 0.0922(13) Uani 1 1 d . . .
C20 C 0.3777(6) 0.5401(4) 0.2276(4) 0.0971(13) Uani 1 1 d . . .
C24 C -0.0081(3) 0.7449(4) -0.3578(3) 0.0888(11) Uani 1 1 d . . .
H24 H -0.0590 0.6871 -0.4017 0.107 Uiso 1 1 calc R . .
C10 C 0.4829(5) 1.2403(4) 0.0676(5) 0.0921(12) Uani 1 1 d . . .
C25 C 0.0371(5) 0.8448(5) -0.4117(4) 0.0990(15) Uani 1 1 d . . .
C26 C 0.1116(5) 0.9282(5) -0.3478(4) 0.0994(13) Uani 1 1 d . . .
H20 H 0.442(3) 0.513(3) 0.182(2) 0.053(9) Uiso 1 1 d . . .
H10A H 0.393(4) 1.255(4) 0.032(3) 0.115(14) Uiso 1 1 d . . .
C17 C 0.2968(3) 0.6775(3) 0.4065(3) 0.0696(9) Uani 1 1 d . . .
H15B H 0.203(3) 0.855(2) -0.014(2) 0.063(8) Uiso 1 1 d . . .
H2 H 0.532(2) 0.874(2) 0.215(2) 0.040(6) Uiso 1 1 d . . .
H15A H 0.170(3) 0.722(3) -0.030(2) 0.061(9) Uiso 1 1 d . . .
H23 H -0.008(3) 0.661(3) -0.198(3) 0.076(10) Uiso 1 1 d . . .
H6A H 0.279(3) 1.081(2) 0.122(2) 0.062(8) Uiso 1 1 d . . .
H10B H 0.545(3) 1.306(3) 0.092(3) 0.092(10) Uiso 1 1 d . . .
H10C H 0.534(5) 1.198(4) 0.001(4) 0.134(17) Uiso 1 1 d . . .
H3A H 0.692(3) 0.991(2) 0.351(2) 0.072(9) Uiso 1 1 d . . .
H8A H 0.697(3) 0.747(3) 0.364(3) 0.073(9) Uiso 1 1 d . . .
H9B H 0.336(4) 0.910(3) 0.475(2) 0.082(10) Uiso 1 1 d . . .
H4B H 0.654(3) 1.063(3) 0.145(3) 0.091(11) Uiso 1 1 d . . .
H9A H 0.437(3) 0.834(3) 0.559(3) 0.079(11) Uiso 1 1 d . . .
H4A H 0.678(3) 1.175(3) 0.248(3) 0.085(10) Uiso 1 1 d . . .
H8B H 0.644(3) 0.724(3) 0.490(3) 0.063(9) Uiso 1 1 d . . .
H1 H 0.320(2) 1.0051(18) 0.3086(18) 0.025(5) Uiso 1 1 d . . .
H5 H 0.438(2) 1.198(2) 0.240(2) 0.037(6) Uiso 1 1 d . . .
H14 H -0.059(2) 0.749(2) 0.004(2) 0.053(7) Uiso 1 1 d . . .
H6B H 0.407(2) 1.012(2) 0.079(2) 0.055(8) Uiso 1 1 d . . .
H13 H 0.101(3) 0.699(3) 0.159(2) 0.059(8) Uiso 1 1 d . . .
H17 H 0.272(3) 0.730(3) 0.476(3) 0.100(12) Uiso 1 1 d . . .
H27 H 0.180(3) 0.971(3) -0.184(3) 0.070(11) Uiso 1 1 d . . .
H21 H 0.547(3) 0.669(2) 0.228(2) 0.063(9) Uiso 1 1 d . . .
H19 H 0.190(5) 0.425(5) 0.263(4) 0.190(18) Uiso 1 1 d . . .
H9C H 0.510(3) 0.957(3) 0.528(3) 0.089(9) Uiso 1 1 d . . .
H18 H 0.136(5) 0.547(4) 0.422(4) 0.135(15) Uiso 1 1 d . . .
H25 H 0.013(3) 0.845(3) -0.499(3) 0.101(11) Uiso 1 1 d . . .
H8C H 0.708(3) 0.863(3) 0.475(2) 0.082(9) Uiso 1 1 d . . .
H3B H 0.565(3) 1.058(3) 0.386(3) 0.086(12) Uiso 1 1 d . . .
H26 H 0.147(4) 1.006(4) -0.375(3) 0.116(14) Uiso 1 1 d . . .
H3O H -0.074(5) 0.828(5) 0.265(4) 0.16(2) Uiso 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
O1 C11 1.318(3) . ?
O1 C1 1.471(3) . ?
N O5 1.193(3) . ?
N O4 1.206(3) . ?
N C14 1.505(3) . ?
O2 C11 1.206(3) . ?
C2 C1 1.525(4) . ?
C2 C3 1.536(4) . ?
C2 C7 1.555(4) . ?
C13 O3 1.401(3) . ?
C13 C11 1.500(4) . ?
C13 C14 1.533(3) . ?
C6 C1 1.505(4) . ?
C6 C5 1.516(4) . ?
C14 C15 1.507(4) . ?
C16 C21 1.361(4) . ?
C16 C17 1.390(4) . ?
C16 C7 1.526(4) . ?
C7 C9 1.533(4) . ?
C7 C8 1.537(4) . ?
C15 C22 1.498(4) . ?
C4 C5 1.510(4) . ?
C4 C3 1.511(5) . ?
C22 C27 1.367(4) . ?
C22 C23 1.369(4) . ?
C21 C20 1.445(6) . ?
C5 C10 1.516(5) . ?
C23 C24 1.374(5) . ?
C27 C26 1.374(5) . ?
C19 C18 1.328(6) . ?
C19 C20 1.352(6) . ?
C18 C17 1.379(5) . ?
C24 C25 1.363(6) . ?
C25 C26 1.351(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101733282
