Catalytic asymmetric aldol addition reactions of 3-fluoro-indolinone derived enolates.
Zhang, Lijun; Zhang, Wenzhong; Mei, Haibo; Han, Jianlin; Soloshonok, Vadim A.; Pan, Yi; Organic & biomolecular chemistry 15 (2017) 311–315; doi:10.1039/c6ob02454h

data_7155388
_publ_section_title
;
 Catalytic asymmetric aldol addition reactions of 3-fluoro-indolinone
 derived enolates.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              311
_journal_page_last               315
_journal_paper_doi               10.1039/c6ob02454h
_journal_volume                  15
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H13 Br F N O2'
_chemical_formula_weight         350.18
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-09-30 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                96.579(2)
_cell_angle_beta                 96.368(2)
_cell_angle_gamma                90.008(2)
_cell_formula_units_Z            4
_cell_length_a                   7.9939(5)
_cell_length_b                   8.0488(4)
_cell_length_c                   22.5543(13)
_cell_measurement_reflns_used    5344
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.52
_cell_measurement_theta_min      2.55
_cell_volume                     1432.60(14)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10475
_diffrn_reflns_point_group_measured_fraction_full 0.694
_diffrn_reflns_point_group_measured_fraction_max 0.694
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         2.548
_exptl_absorpt_coefficient_mu    2.884
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.022(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     765
_refine_ls_number_reflns         7048
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0226P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0809
_reflns_Friedel_coverage         0.394
_reflns_Friedel_fraction_full    0.392
_reflns_Friedel_fraction_max     0.392
_reflns_number_gt                6228
_reflns_number_total             7048
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02454h2.cif
_cod_data_source_block           1_a
_cod_depositor_comments          'Adding full bibliography for 7155388.cif.'
_cod_database_code               7155388
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.510
_shelx_estimated_absorpt_t_max   0.570
_shelx_res_checksum              79782
_shelx_hkl_checksum              10425