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_4035028
_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_formula_moiety         'C6 H9 I2 N O'
_chemical_formula_sum            'C6 H9 I2 N O'
_chemical_formula_weight         364.94
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.685(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4152(16)
_cell_length_b                   8.0644(15)
_cell_length_c                   13.713(3)
_cell_measurement_reflns_used    5593
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.65
_cell_measurement_theta_min      2.43
_cell_volume                     928.7(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8796
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.705
_diffrn_reflns_theta_min         2.425
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.713
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0746 before and 0.0439 after correction. The Ratio of minimum to maximum transmission is 0.6907. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.610
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.706
_refine_diff_density_min         -2.142
_refine_diff_density_rms         0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         2859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0374P)^2^+1.7445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0876
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2485
_reflns_number_total             2859
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01424_si_002.cif
_cod_data_source_block           mo_dm17439_0m
_cod_database_code               4035028
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.500
_shelx_estimated_absorpt_t_min   0.347
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_shelx_res_checksum              15873
_shelx_hkl_checksum              28025
_olex2_submission_special_instructions 'No special instructions were received'