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_4515814
_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         401.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                79.500(6)
_cell_angle_beta                 87.548(7)
_cell_angle_gamma                81.464(7)
_cell_formula_units_Z            2
_cell_length_a                   8.535(3)
_cell_length_b                   10.595(4)
_cell_length_c                   11.444(4)
_cell_measurement_reflns_used    1801
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.698
_cell_measurement_theta_min      2.413
_cell_volume                     1006.1(6)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.9638
_diffrn_measured_fraction_theta_max 0.9638
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9541
_diffrn_reflns_theta_full        28.4545
_diffrn_reflns_theta_max         28.45
_diffrn_reflns_theta_min         1.81
_diffrn_source_current           5.0
_diffrn_source_power             0.1
_diffrn_source_voltage           20.0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9
_exptl_absorpt_correction_T_min  0.753283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.05 (BRUKER, 2001) was used for absorption correction.
R(int) was 0.0416 before and 0.0224 after correction.
The Ratio of minimum to maximum transmission is 0.7533.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.3250
_exptl_crystal_description       block
_exptl_crystal_F_000             424.2213
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.5054
_refine_diff_density_min         -0.4060
_refine_diff_density_rms         0.0954
_refine_ls_d_res_high            0.7458
_refine_ls_d_res_low             11.2510
_refine_ls_goodness_of_fit_ref   0.8733
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.8733
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.0651
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1162P)^2^+0.6108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1855
_refine_ls_wR_factor_ref         0.2245
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2714
_reflns_number_total             4895
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            cs8b04079_si_002.cif
_cod_data_source_block           gul2s
_cod_original_cell_volume        1006.2(6)
_cod_database_code               4515814
_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), C13(H13), C14(H14), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b), C17(H17a,H17b), C18(H18a,H18b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_olex2_submission_special_instructions 'No special instructions were received'