Photoredox-Mediated Minisci-type Alkylation of N-Heteroarenes with Alkanes with High Methylene Selectivity
Li, Guo-Xing; Hu, Xiafei; He, Gang; Chen, Gong; ACS Catalysis 8 (2018) 11847–; doi:10.1021/acscatal.8b04079

data_4515815
_publ_section_title
;
 Photoredox-Mediated Minisci-type Alkylation of N-Heteroarenes with
 Alkanes with High Methylene Selectivity
;
_journal_issue                   12
_journal_name_full               'ACS Catalysis'
_journal_page_first              11847
_journal_paper_doi               10.1021/acscatal.8b04079
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C25 H23 N O4'
_chemical_formula_sum            'C25 H23 N O4'
_chemical_formula_weight         401.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                68.032(7)
_cell_angle_beta                 80.699(7)
_cell_angle_gamma                75.858(8)
_cell_formula_units_Z            2
_cell_length_a                   9.737(4)
_cell_length_b                   10.551(4)
_cell_length_c                   11.090(4)
_cell_measurement_reflns_used    1567
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      26.177
_cell_measurement_theta_min      2.338
_cell_volume                     1021.5(7)
_computing_cell_refinement       'SAINT V6.36A (BRUKER, 2016)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.36A (BRUKER, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      198(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8959
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.82
_diffrn_reflns_theta_min         1.99
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           32.0
_diffrn_source_power             1.6
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9
_exptl_absorpt_correction_T_min  0.806472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.05 (BRUKER, 2001) was used for absorption correction.
R(int) was 0.0461 before and 0.0161 after correction.
The Ratio of minimum to maximum transmission is 0.8065.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pyramid
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1313
_refine_ls_R_factor_gt           0.0715
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1047P)^2^+0.0510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1845
_refine_ls_wR_factor_ref         0.2193
_reflns_number_gt                2616
_reflns_number_total             5089
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs8b04079_si_003.cif
_cod_data_source_block           gul4s
_cod_database_code               4515815
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C14(H14), C17(H17), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C11(H11), C22(H22), C8(H8), C21(H21), C9(H9), C25(H25), C10(H10),
 C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'