σ N-C Bond Difunctionalization in Bridged Twisted Amides: Sew-and-Cut Activation Approach to Functionalized Isoquinolines.
Hu, Feng; Nareddy, Pradeep; Lalancette, Roger; Jordan, Frank; Szostak, Michal; Organic letters 19 (2017) 2386–2389; doi:10.1021/acs.orglett.7b00913

data_1545799
_publ_section_title
;
 \s N-C Bond Difunctionalization in Bridged Twisted Amides: Sew-and-Cut
 Activation Approach to Functionalized Isoquinolines.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2386
_journal_page_last               2389
_journal_paper_doi               10.1021/acs.orglett.7b00913
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.637(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2899(6)
_cell_length_b                   10.1880(5)
_cell_length_c                   8.5203(5)
_cell_measurement_reflns_used    4823
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.48
_cell_measurement_theta_min      3.92
_cell_volume                     978.04(9)
_computing_cell_refinement       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'Bruker SMART CCD Apex-II area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8051
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.956
_diffrn_reflns_theta_min         3.923
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008a)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       tablet
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0027(5)
_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   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0422P)^2^+0.3128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1467
_reflns_number_total             1694
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00913_si_002.cif
_cod_data_source_block           FENG7_a
_cod_depositor_comments          'Adding full bibliography for 1545799.cif.'
_cod_database_code               1545799
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.867
_shelx_estimated_absorpt_t_max   0.940
_shelx_res_checksum              94569
_shelx_hkl_checksum              43735