Mn-Mediated Radical-Ionic Annulations of Chiral N-Acylhydrazones.
Slater, Kara A.; Friestad, Gregory K.; The Journal of organic chemistry 80 (2015) 6432–6440; doi:10.1021/acs.joc.5b00863

data_4031040
_publ_section_title
;
 Mn-Mediated Radical-Ionic Annulations of Chiral N-Acylhydrazones.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6432
_journal_page_last               6440
_journal_paper_doi               10.1021/acs.joc.5b00863
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H24 N2 O2'
_chemical_formula_weight         288.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2911(14)
_cell_length_b                   11.5932(13)
_cell_length_c                   12.2066(14)
_cell_measurement_reflns_used    5022
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      45.7
_cell_measurement_theta_min      4.8
_cell_volume                     1597.8(3)
_computing_cell_refinement       'APEX II, (Bruker AXS, 2014)'
_computing_data_collection       'APEX II, (Bruker AXS, 2014)'
_computing_data_reduction        'APEX II, (Bruker AXS, 2014)'
_computing_molecular_graphics    'APEX II, (Bruker AXS, 2014)'
_computing_publication_material  'APEX II, (Bruker AXS, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'APEX II, (Bruker AXS, 2014)'
_diffrn_ambient_temperature      190(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Nonius Bruker APEX II'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20975
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.417
_diffrn_reflns_theta_min         3.021
_diffrn_source                   'Mo-target fine-focus sealed-tube'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1225 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         4462
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0403P)^2^+0.0900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0893
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.888
_reflns_number_gt                3411
_reflns_number_total             4462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00863_si_001.cif
_cod_data_source_block           fri141c
_cod_depositor_comments          'Adding full bibliography for 4031040.cif.'
_cod_database_code               4031040
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2014-3
_shelx_res_checksum              97852
_shelx_hkl_checksum              10815