Silylation-Based Kinetic Resolution of α-Hydroxy Lactones and Lactams.
Clark, Robert W.; Deaton, T. Maxwell; Zhang, Yan; Moore, Maggie I.; Wiskur, Sheryl L.; Organic letters 15 (2013) 6132–6135; doi:10.1021/ol402982w

data_1513230
_publ_section_title
;
 Silylation-Based Kinetic Resolution of \a-Hydroxy Lactones and Lactams.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6132
_journal_page_last               6135
_journal_paper_doi               10.1021/ol402982w
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H33 N O2 Si'
_chemical_formula_sum            'C33 H33 N O2 Si'
_chemical_formula_weight         503.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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-2013
_cell_angle_alpha                90
_cell_angle_beta                 91.991(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9327(14)
_cell_length_b                   11.455(2)
_cell_length_c                   14.741(3)
_cell_measurement_reflns_used    1648
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.00
_cell_measurement_theta_min      2.25
_cell_volume                     1338.7(4)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.631 (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
; 
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, 
OLEX2: a complete structure solution, refinement and analysis program. 
J. Appl. Cryst. (2009). 42, 339-341. 
;
_computing_publication_material
; 
C. B. H\"ubschle, G. M. Sheldrick and B. Dittrich, ShelXle: a Qt graphical 
user interface for SHELXL. J. Appl. Cryst. (2011). 44, 1281-1284. 
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14904
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.057
_diffrn_reflns_theta_min         1.382
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.842677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS v.2.10 (Bruker,2003) was used for absorption correction. 
R(int) was 0.0606 before and 0.0490 after correction. 
The Ratio of minimum to maximum transmission is 0.8427. 
The \l/2 correction factor is 0.0015. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
; 
 Flack x determined using 1613 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.09(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4731
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0300P)^2^] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4034
_reflns_number_total             4731
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol402982w_si_002.cif
_cod_data_source_block           LactamTable3Entry7
_cod_database_code               1513230
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.986