Switchable electrooxidative N-methyl amines: access to C3-aminomethylated and C3-arylmethylated imidazo[1,2-a] pyridines
Li, Sifeng; Wang, Taimin; Li, Xingchen; Fang, Lijing; Zhai, Hongbin; Cheng, Bin; Green Chemistry 24 (2022) 9482–9488; doi:10.1039/D2GC03464F

data_7245762
_publ_section_title
;
 Switchable electrooxidative N-methyl amines: access to C3-aminomethylated
 and C3-arylmethylated imidazo[1,2-a] pyridines
;
_journal_issue                   24
_journal_name_full               'Green Chemistry'
_journal_page_first              9482
_journal_page_last               9488
_journal_paper_doi               10.1039/D2GC03464F
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C19 H17 N3 S'
_chemical_formula_sum            'C19 H17 N3 S'
_chemical_formula_weight         319.41
_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     dual
_audit_creation_date             2021-11-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2022-04-11 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                65.8180(10)
_cell_angle_beta                 86.3210(10)
_cell_angle_gamma                79.4170(10)
_cell_formula_units_Z            2
_cell_length_a                   8.3612(2)
_cell_length_b                   9.7442(2)
_cell_length_c                   10.6475(2)
_cell_measurement_reflns_used    6127
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      68.192
_cell_measurement_theta_min      4.553
_cell_volume                     777.84(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10004
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.186
_diffrn_reflns_theta_min         4.552
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.853
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1085 before and 0.0694 after correction.
The Ratio of minimum to maximum transmission is 0.8598.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         2825
_refine_ls_number_restraints     872
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0515P)^2^+0.3640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2607
_reflns_number_total             2825
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc03464f2.cif
_cod_data_source_block           846_lsf_0m
_cod_depositor_comments
'Adding full bibliography for 7245762--7245764.cif.'
_cod_database_code               7245762
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.866
_shelx_estimated_absorpt_t_min   0.708
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S1A-C12A \\sim S1A-C9A \\sim S1B-C9B \\sim S1B-C12B
 with sigma of 0.02
 C9B-C10B \\sim C11B-C12B \\sim C12A-C11A \\sim C10A-C9A
 with sigma of 0.02
 C10B-C11B \\sim C10A-C11A
 with sigma of 0.02
 S1B-C11B \\sim S1B-C10B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(S1B)=Sof(N2B)=Sof(C19B)=Sof(C18B)=Sof(H18B)=Sof(C17B)=Sof(H17B)=Sof(C16B)=
 Sof(H16B)=Sof(C15B)=Sof(H15B)=Sof(N3B)=Sof(H8BD)=Sof(H8BC)=Sof(C9B)=Sof(H9B)=
 Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(C13B)=Sof(C14B)=1-FVAR(1)
 Sof(S1A)=Sof(H8AB)=Sof(H8AA)=Sof(N2A)=Sof(N3A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=
 Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(C13A)=Sof(C14A)=Sof(C15A)=
 Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=
 Sof(C19A)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C8(H8AB,H8AA), C8(H8BD,H8BC)
6.b Aromatic/amide H refined with riding coordinates:
 C18B(H18B), C17B(H17B), C16B(H16B), C15B(H15B), C2(H2), C3(H3), C4(H4),
 C5(H5), C6(H6), C9B(H9B), C10B(H10B), C11B(H11B), C9A(H9A), C10A(H10A),
 C11A(H11A), C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A)
6.c Fitted hexagon refined as free rotating group:
 N2B(C19B,C18B,C17B,C16B,C15B)
6.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              53353
_olex2_submission_special_instructions 'No special instructions were received'