Catalyst Control over Regio- and Enantioselectivity in Baeyer-Villiger Oxidations of Functionalized Ketones.
Romney, David K.; Colvin, Sean M.; Miller, Scott J.; Journal of the American Chemical Society 136 (2014) 14019–; doi:10.1021/ja508757g

data_4122704
_publ_contact_author
;
 Prof. Scott J. Miller         
 The Department of Chemistry 
 Yale University 
 P. O. Box 208107 
 New Haven 
 Connecticut 06520 USA.
;
_publ_section_title
;
 Catalyst Control over Regio- and Enantioselectivity in Baeyer-Villiger
 Oxidations of Functionalized Ketones.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14019
_journal_paper_doi               10.1021/ja508757g
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_sum            'C14 H17 N O2'
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_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
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_symmetry_space_group_name_H-M   'F d d 2'
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_cell_angle_gamma                90
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_cell_length_b                   50.228(4)
_cell_length_c                   5.1431(2)
_cell_measurement_reflns_used    8825
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_cell_measurement_theta_max      67.6
_cell_measurement_theta_min      3.5
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_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_molecular_graphics
;
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program
(2009). J. Appl. Cryst., 42, 339-341.
;
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_R_equivalents  0.2047
_diffrn_reflns_av_unetI/netI     0.0976
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_diffrn_reflns_Laue_measured_fraction_max 0.985
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_diffrn_reflns_limit_k_max       60
_diffrn_reflns_limit_k_min       -60
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            31682
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.180
_diffrn_reflns_theta_min         3.520
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
; 
 Flack x determined using 430 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2101
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0733
_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^)+(0.0893P)^2^+8.5014P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1870
_refine_ls_wR_factor_ref         0.2213
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                1420
_reflns_number_total             2101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja508757g_si_002.cif
_cod_data_source_block           007-14122
_cod_depositor_comments
'Adding full bibliography for 4122703--4122704.cif.'
_cod_original_cell_volume        4792.8(4)
_cod_database_code               4122704
_shelx_estimated_absorpt_t_min   0.821
_shelx_estimated_absorpt_t_max   0.986
_shelxl_version_number           2013-4
_shelx_res_checksum              52866
_shelx_hkl_checksum              2859