Synthesis and kinetic resolution of substituted tetrahydroquinolines by lithiation then electrophilic quench.
Carter, Nicholas; Li, Xiabing; Reavey, Lewis; Meijer, Anthony J. H. M.; Coldham, Iain; Chemical science 9 (2018) 1352–1357; doi:10.1039/c7sc04435f

data_1548458
_publ_section_title
;
 Synthesis and kinetic resolution of substituted tetrahydroquinolines by
 lithiation then electrophilic quench.
;
_journal_issue                   5
_journal_name_full               'Chemical science'
_journal_page_first              1352
_journal_page_last               1357
_journal_paper_doi               10.1039/c7sc04435f
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H27 N O4'
_chemical_formula_sum            'C23 H27 N O4'
_chemical_formula_weight         381.45
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-10-05 deposited with the CCDC.
2017-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.258(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4950(3)
_cell_length_b                   8.8357(3)
_cell_length_c                   12.0617(4)
_cell_measurement_reflns_used    8464
_cell_measurement_temperature    97(2)
_cell_measurement_theta_max      66.52
_cell_measurement_theta_min      3.66
_cell_volume                     1011.91(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      97(2)
_diffrn_measured_fraction_theta_full 0.997
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14554
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        66.614
_diffrn_reflns_theta_max         66.614
_diffrn_reflns_theta_min         3.664
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
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_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
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_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
; 
 Flack x determined using 1271 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.11(12)
_refine_ls_extinction_coef       0.0107(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0411P)^2^+0.0980P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0786
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                3116
_reflns_number_total             3491
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc04435f2.cif
_cod_data_source_block           CARTERN2_0m
_cod_depositor_comments
'Adding full bibliography for 1548455--1548458.cif.'
_cod_database_code               1548458
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.810
_shelx_estimated_absorpt_t_max   0.941
_shelx_res_checksum              78915