A Simple Primary Amine Catalyst for Enantioselective α-Hydroxylations and α-Fluorinations of Branched Aldehydes.
Witten, Michael R.; Jacobsen, Eric N.; Organic letters 17 (2015) 2772–2775; doi:10.1021/acs.orglett.5b01193

data_1519696
_publ_section_title
;
 A Simple Primary Amine Catalyst for Enantioselective \a-Hydroxylations
 and \a-Fluorinations of Branched Aldehydes.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2772
_journal_page_last               2775
_journal_paper_doi               10.1021/acs.orglett.5b01193
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H13 F O'
_chemical_formula_weight         204.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   6.1061(2)
_cell_length_b                   18.8064(5)
_cell_length_c                   27.8827(7)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.7
_cell_measurement_theta_min      2.83
_cell_volume                     3201.88(16)
_computing_cell_refinement       'SAINT 8.34C (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 v2014.3.0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT 8.34C (Bruker-AXS, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            56690
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.679
_diffrn_reflns_theta_min         2.834
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  0.8642
_exptl_absorpt_correction_T_min  0.7732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       needle
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1993 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5672
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0610P)^2^+0.6390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                5034
_reflns_number_total             5672
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01193_si_003.cif
_cod_data_source_block           fluoro-2-nap-needle
_cod_depositor_comments
;
Adding full bibliography for 1519696--1519698.cif.

2019-08-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C39 H39 F3 O3'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     612.70
_cod_database_code               1519696
_shelx_estimated_absorpt_t_min   0.891
_shelx_estimated_absorpt_t_max   0.957
_shelxl_version_number           2014/6
_shelx_res_checksum              15387
_shelx_hkl_checksum              89867