Asymmetric synthesis of C–F quaternary α-fluoro-β-amino-indolin-2-ones via Mannich addition reactions; facets of reactivity, structural generality and stereochemical outcome
Xie, Chen; Sha, Wanxing; Zhu, Yi; Han, Jianlin; Soloshonok, Vadim A.; Pan, Yi; RSC Adv. 7 (2017) 5679–; doi:10.1039/C6RA27710A

data_7227464
_publ_section_title
;
 Asymmetric synthesis of C--F quaternary \a-fluoro-\b-amino-indolin-2-ones
 via Mannich addition reactions; facets of reactivity, structural
 generality and stereochemical outcome
;
_journal_issue                   10
_journal_name_full               'RSC Adv.'
_journal_page_first              5679
_journal_paper_doi               10.1039/C6RA27710A
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H23 F N2 O2 S'
_chemical_formula_weight         374.46
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_Hall           'P 4cw'
_space_group_name_H-M_alt        'P 43'
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-03-02 deposited with the CCDC.
2016-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.6264(4)
_cell_length_b                   9.6264(4)
_cell_length_c                   42.6146(18)
_cell_measurement_temperature    296(2)
_cell_volume                     3949.0(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0450
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            23684
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         2.116
_exptl_absorpt_coefficient_mu    0.189
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1759 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         6527
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+0.4827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.866
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                5054
_reflns_number_total             6527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra27710a2.cif
_cod_data_source_block           20151103PYXC1_0m_a_a
_cod_original_cell_volume        3949.0(4)
_cod_database_code               7227464
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.949
_shelx_estimated_absorpt_t_max   0.960
_shelx_res_checksum              25168