Asymmetric Synthesis of Isoquinolinonaphthyridines Catalyzed by a Chiral Brønsted Acid
Li, Jianjun; Fu, Yiwei; Qin, Cong; Yu, Yang; Li, Hao; Wang, Wei; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01527E

data_7155774
_publ_section_title
;
 Asymmetric Synthesis of Isoquinolinonaphthyridines Catalyzed by a Chiral
 Br\/onsted Acid
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01527E
_journal_year                    2017
_chemical_formula_moiety         'C22 H21 Br N2 O2'
_chemical_formula_sum            'C22 H21 Br N2 O2'
_chemical_formula_weight         425.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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
;
2016-11-05 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                66.936(2)
_cell_angle_beta                 86.111(2)
_cell_angle_gamma                76.562(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1340(3)
_cell_length_b                   10.0111(4)
_cell_length_c                   11.6697(4)
_cell_measurement_reflns_used    9629
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      68.11
_cell_measurement_theta_min      4.12
_cell_volume                     954.60(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.982
_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  0.0433
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20485
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.291
_diffrn_reflns_theta_min         4.119
_exptl_absorpt_coefficient_mu    3.089
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0598P)^2^+0.8683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1247
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2646
_reflns_number_total             3426
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01527e2.cif
_cod_data_source_block           t_0m_a
_cod_database_code               7155774
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.577
_shelx_estimated_absorpt_t_max   0.577
_shelx_res_checksum              45855