#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/54/4025400.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_4025400
loop_
_publ_author_name
'Alexander M. R. Smith'
'Henry S. Rzepa'
'Andrew J. P. White'
'Denis Billen'
'King Kuok (Mimi) Hii'
_publ_section_title
;
 Delineating Origins of Stereocontrol in Asymmetric Pd-Catalyzed
 α-Hydroxylation of 1,3-Ketoesters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3085
_journal_page_last               3096
_journal_paper_doi               10.1021/jo1002906
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H21 N O6'
_chemical_formula_sum            'C17 H21 N O6'
_chemical_formula_weight         335.35
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.2709(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.34741(7)
_cell_length_b                   10.76431(9)
_cell_length_c                   12.86992(13)
_cell_measurement_reflns_used    15163
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.3109
_cell_measurement_theta_min      3.5090
_cell_volume                     859.254(15)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.2556
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22418
_diffrn_reflns_theta_full        72.47
_diffrn_reflns_theta_max         72.47
_diffrn_reflns_theta_min         3.51
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) 
(compiled Sep 15 2009,11:49:04) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablets
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1596 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.04(12)
_refine_ls_extinction_coef       0.0053(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3386
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0259
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0424P)²+0.0832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0688
_reflns_number_gt                3221
_reflns_number_total             3386
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1002906_si_001.cif
_cod_data_source_block           (S)-(+)-20b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025400
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
N1 N 0.31910(17) 0.56309(10) 0.91265(8) 0.0294(2) Uani 1 1 d . . .
C2 C 0.35000(19) 0.47957(11) 0.83667(10) 0.0292(3) Uani 1 1 d . . .
O2 O 0.50492(15) 0.47546(11) 0.79589(8) 0.0445(3) Uani 1 1 d . . .
C3 C 0.15638(19) 0.39039(10) 0.81303(9) 0.0270(3) Uani 1 1 d . . .
C4 C 0.0178(2) 0.43113(12) 0.88996(10) 0.0307(3) Uani 1 1 d . . .
H4A H -0.1302 0.4512 0.8511 0.037 Uiso 1 1 calc R . .
H4B H 0.0098 0.3645 0.9420 0.037 Uiso 1 1 calc R . .
C5 C 0.1262(2) 0.54451(11) 0.94529(10) 0.0301(3) Uani 1 1 d . . .
O5 O 0.06275(17) 0.61028(10) 1.00825(8) 0.0435(2) Uani 1 1 d . . .
C6 C 0.4800(2) 0.65655(12) 0.95959(11) 0.0364(3) Uani 1 1 d . . .
H6A H 0.6252 0.6188 0.9703 0.044 Uiso 1 1 calc R . .
H6B H 0.4551 0.6802 1.0303 0.044 Uiso 1 1 calc R . .
C7 C 0.4758(2) 0.77232(12) 0.89320(10) 0.0318(3) Uani 1 1 d . . .
C8 C 0.3013(2) 0.85371(13) 0.87800(12) 0.0375(3) Uani 1 1 d . . .
H8A H 0.1781 0.8325 0.9052 0.045 Uiso 1 1 calc R . .
C9 C 0.3036(2) 0.96444(12) 0.82421(12) 0.0370(3) Uani 1 1 d . . .
H9A H 0.1827 1.0185 0.8144 0.044 Uiso 1 1 calc R . .
C10 C 0.4834(2) 0.99652(12) 0.78448(10) 0.0304(3) Uani 1 1 d . . .
C11 C 0.6571(2) 0.91644(13) 0.79716(12) 0.0372(3) Uani 1 1 d . . .
H11A H 0.7797 0.9372 0.7693 0.045 Uiso 1 1 calc R . .
C12 C 0.6503(2) 0.80488(12) 0.85130(12) 0.0376(3) Uani 1 1 d . . .
H12A H 0.7695 0.7497 0.8595 0.045 Uiso 1 1 calc R . .
O13 O 0.47532(15) 1.11039(9) 0.73494(7) 0.0366(2) Uani 1 1 d . . .
C14 C 0.6738(2) 1.16105(14) 0.71787(12) 0.0419(3) Uani 1 1 d . . .
H14A H 0.7253 1.1111 0.6647 0.063 Uiso 1 1 calc R . .
H14B H 0.7816 1.1600 0.7848 0.063 Uiso 1 1 calc R . .
H14C H 0.6502 1.2468 0.6924 0.063 Uiso 1 1 calc R . .
O15 O 0.22678(16) 0.26773(8) 0.83508(7) 0.0355(2) Uani 1 1 d D . .
H15 H 0.287(3) 0.2426(17) 0.7815(10) 0.054(5) Uiso 1 1 d D . .
C16 C 0.0495(2) 0.40412(12) 0.69540(10) 0.0287(2) Uani 1 1 d . . .
O16 O 0.05656(18) 0.32289(9) 0.63210(8) 0.0434(2) Uani 1 1 d . . .
O17 O -0.04136(15) 0.51462(8) 0.67707(7) 0.0341(2) Uani 1 1 d . . .
C18 C -0.1529(2) 0.55191(14) 0.56741(11) 0.0410(3) Uani 1 1 d . . .
C19 C 0.0066(3) 0.55334(16) 0.49551(13) 0.0513(4) Uani 1 1 d . . .
H19A H 0.1260 0.6094 0.5250 0.077 Uiso 1 1 calc R . .
H19B H -0.0653 0.5823 0.4246 0.077 Uiso 1 1 calc R . .
H19C H 0.0626 0.4693 0.4903 0.077 Uiso 1 1 calc R . .
C20 C -0.3412(3) 0.4644(2) 0.52864(14) 0.0588(5) Uani 1 1 d . . .
H20A H -0.2864 0.3805 0.5208 0.088 Uiso 1 1 calc R . .
H20B H -0.4241 0.4933 0.4598 0.088 Uiso 1 1 calc R . .
H20C H -0.4344 0.4629 0.5803 0.088 Uiso 1 1 calc R . .
C21 C -0.2294(4) 0.68197(18) 0.58509(16) 0.0681(6) Uani 1 1 d . . .
H21A H -0.1046 0.7355 0.6113 0.102 Uiso 1 1 calc R . .
H21B H -0.3209 0.6794 0.6376 0.102 Uiso 1 1 calc R . .
H21C H -0.3123 0.7152 0.5178 0.102 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 112.91(10) . . ?
C2 N1 C6 123.33(11) . . ?
C5 N1 C6 123.64(11) . . ?
O2 C2 N1 125.82(12) . . ?
O2 C2 C3 125.48(11) . . ?
N1 C2 C3 108.70(10) . . ?
O15 C3 C4 110.04(10) . . ?
O15 C3 C16 110.27(9) . . ?
C4 C3 C16 114.84(10) . . ?
O15 C3 C2 109.90(10) . . ?
C4 C3 C2 103.85(10) . . ?
C16 C3 C2 107.67(10) . . ?
C5 C4 C3 105.81(10) . . ?
O5 C5 N1 123.97(12) . . ?
O5 C5 C4 127.54(13) . . ?
N1 C5 C4 108.49(10) . . ?
N1 C6 C7 113.95(10) . . ?
C12 C7 C8 117.83(12) . . ?
C12 C7 C6 120.91(12) . . ?
C8 C7 C6 121.13(12) . . ?
C9 C8 C7 121.39(13) . . ?
C8 C9 C10 119.75(13) . . ?
O13 C10 C11 124.06(12) . . ?
O13 C10 C9 116.02(11) . . ?
C11 C10 C9 119.92(12) . . ?
C10 C11 C12 119.19(12) . . ?
C7 C12 C11 121.91(13) . . ?
C10 O13 C14 117.55(11) . . ?
O16 C16 O17 127.70(12) . . ?
O16 C16 C3 121.87(11) . . ?
O17 C16 C3 110.42(10) . . ?
C16 O17 C18 120.80(10) . . ?
O17 C18 C19 109.70(12) . . ?
O17 C18 C21 102.07(12) . . ?
C19 C18 C21 111.15(14) . . ?
O17 C18 C20 108.99(12) . . ?
C19 C18 C20 112.83(15) . . ?
C21 C18 C20 111.54(16) . . ?
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
N1 C2 1.3728(16) . ?
N1 C5 1.3909(17) . ?
N1 C6 1.4689(16) . ?
C2 O2 1.2098(16) . ?
C2 C3 1.5380(17) . ?
C3 O15 1.4034(14) . ?
C3 C4 1.5220(17) . ?
C3 C16 1.5288(17) . ?
C4 C5 1.5038(18) . ?
C5 O5 1.2077(16) . ?
C6 C7 1.5080(19) . ?
C7 C12 1.376(2) . ?
C7 C8 1.393(2) . ?
C8 C9 1.3801(19) . ?
C9 C10 1.3898(19) . ?
C10 O13 1.3776(16) . ?
C10 C11 1.3817(18) . ?
C11 C12 1.394(2) . ?
O13 C14 1.4317(17) . ?
C16 O16 1.2024(16) . ?
C16 O17 1.3210(16) . ?
O17 C18 1.4932(16) . ?
C18 C19 1.510(2) . ?
C18 C21 1.515(2) . ?
C18 C20 1.520(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659189
2 PubChem 46218316
