PIDA/I<sub>2</sub>-Mediated α- and β-C(sp<sup>3</sup>)-H Bond Dual Functionalization of Tertiary Amines.
Zhu, Yu; Shao, Li-Dong; Deng, Zhen-Tao; Bao, Ying; Shi, Xin; Zhao, Qin-Shi; The Journal of organic chemistry 83 (2018) 10166–10174; doi:10.1021/acs.joc.8b01424

data_4035029
_publ_section_title
;
 PIDA/I<sub>2</sub>-Mediated \a- and \b-C(sp<sup>3</sup>)-H Bond Dual
 Functionalization of Tertiary Amines.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10166
_journal_page_last               10174
_journal_paper_doi               10.1021/acs.joc.8b01424
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H18 I N O3'
_chemical_formula_sum            'C16 H18 I N O3'
_chemical_formula_weight         399.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 98.1490(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7161(10)
_cell_length_b                   7.7989(9)
_cell_length_c                   10.9853(12)
_cell_measurement_reflns_used    7593
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.82
_cell_measurement_theta_min      2.36
_cell_volume                     739.20(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8173
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.922
_diffrn_reflns_theta_min         1.873
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.780
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   0.1568
_exptl_transmission_factor_min   0.0856
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1802 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4189
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0150
_refine_ls_R_factor_gt           0.0148
_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^)+(0.0057P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0377
_refine_ls_wR_factor_ref         0.0377
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.849
_reflns_number_gt                4140
_reflns_number_total             4189
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01424_si_003.cif
_cod_data_source_block           mo_fzz06011_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4035029
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.282
_shelx_estimated_absorpt_t_max   0.780
_shelx_res_checksum              77796
_shelx_hkl_checksum              10344