The synthesis of optically active N-C axially chiral tetrahydroquinoline and its response to an acid-accelerated molecular rotor
Yuya Suzuki; Masato Kageyama; Ryuichi Morisawa; Yasuo Dobashi; Hiroshi Hasegawa; Satoshi Yokojima; Osamu Kitagawa; Chem.Commun. 51 (2015) 11229–; doi:10.1039/C5cc03659C

data_7117403
_publ_section_title
;
 The synthesis of optically active N-C axially chiral tetrahydroquinoline
 and its response to an acid-accelerated molecular rotor
;
_journal_name_full               Chem.Commun.
_journal_page_first              11229
_journal_paper_doi               10.1039/C5cc03659C
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration .
_chemical_formula_moiety         'C23 H31 N'
_chemical_formula_sum            'C23 H31 N'
_chemical_formula_weight         321.49
_chemical_name_systematic
;
1-(2,5-di-tert-butylphenyl)-1,2,3,4-tetrahydroquinoline
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             '23 April 2014'
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-04-24 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                85.6050(10)
_cell_angle_beta                 74.3180(10)
_cell_angle_gamma                69.6920(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3731(10)
_cell_length_b                   9.7689(10)
_cell_length_c                   11.5285(12)
_cell_measurement_reflns_used    4157
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.40
_cell_volume                     952.97(17)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0243
_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       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9262
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9880
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+0.3069P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0959
_reflns_number_gt                2968
_reflns_number_total             3354
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc03659c2.cif
_cod_data_source_block           p-1
_cod_database_code               7117403