Rhodium(III)-Catalyzed C-H Activation/Heterocyclization as a Macrocyclization Strategy. Synthesis of Macrocyclic Pyridones.
Krieger, Jean-Philippe; Lesuisse, Dominique; Ricci, Gino; Perrin, Marc-Antoine; Meyer, Christophe; Cossy, Janine; Organic letters  (2017) –; doi:10.1021/acs.orglett.7b01051

data_1546009
_publ_section_title
;
 Rhodium(III)-Catalyzed C-H Activation/Heterocyclization as a
 Macrocyclization Strategy. Synthesis of Macrocyclic Pyridones.
;
_journal_name_full               'Organic letters'
_journal_paper_doi               10.1021/acs.orglett.7b01051
_journal_year                    2017
_chemical_formula_sum            'C19 H23 N O4'
_chemical_formula_weight         329.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.370(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.183(4)
_cell_length_b                   6.7949(18)
_cell_length_c                   16.513(4)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.852
_cell_measurement_theta_min      2.469
_cell_volume                     1702.1(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'CCD Smart Apex'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16838
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.029
_diffrn_reflns_theta_min         2.469
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS (Bruker AXS Inc., Madison, Wisconsin, USA)'
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       rod-like
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0729P)^2^+0.2866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1273
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3802
_reflns_number_total             4203
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01051_si_002.cif
_cod_data_source_block           amp372a_a_molecule_10f
_cod_database_code               1546009
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              6295
_shelx_hkl_checksum              30499