Synthesis of Aminophenanthrenes and Benzoquinolines via Hauser-Kraus Annulation of Sulfonyl Phthalide with Rauhut-Currier Adducts of Nitroalkenes.
Kumar, Tarun; Mane, Vaijinath; Namboothiri, Irishi N. N.; Organic letters 19 (2017) 4283–4286; doi:10.1021/acs.orglett.7b01924

data_1547075
_publ_section_title
;
 Synthesis of Aminophenanthrenes and Benzoquinolines via Hauser-Kraus
 Annulation of Sulfonyl Phthalide with Rauhut-Currier Adducts of
 Nitroalkenes.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4283
_journal_page_last               4286
_journal_paper_doi               10.1021/acs.orglett.7b01924
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C20 H14 Cl N O'
_chemical_formula_weight         319.77
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.745(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1638(8)
_cell_length_b                   14.3230(11)
_cell_length_c                   13.4195(10)
_cell_measurement_reflns_used    3000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.7790
_cell_measurement_theta_min      2.5540
_cell_volume                     1494.5(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8424
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.16
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4235
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1192P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.2394
_reflns_number_gt                2650
_reflns_number_total             4235
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b01924_si_001.cif
_cod_data_source_block           inn-tk-556_mo
_cod_database_code               1547075