Copper-catalyzed three-component reaction to synthesize polysubstituted imidazo[1,2-a]pyridines
Zhou, Zitong; Luo, Danyang; Li, Guanrong; Yang, Zhongtao; Cui, Liao; Yang, Weiguang; RSC Advances 12 (2022) 20199–20205; doi:10.1039/D2RA02722D

data_7245203
_publ_section_title
;
 Copper-catalyzed three-component reaction to synthesize polysubstituted
 imidazo[1,2-a]pyridines
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              20199
_journal_page_last               20205
_journal_paper_doi               10.1039/D2RA02722D
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C17 H17 N3 O4 S'
_chemical_formula_sum            'C17 H17 N3 O4 S'
_chemical_formula_weight         359.39
_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
_audit_creation_date             2021-11-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                93.835(2)
_cell_angle_beta                 111.598(2)
_cell_angle_gamma                96.227(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7875(5)
_cell_length_b                   8.8129(5)
_cell_length_c                   11.7354(6)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.508
_cell_measurement_theta_min      3.167
_cell_volume                     834.41(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_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  0.0228
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17497
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.538
_diffrn_reflns_theta_min         3.167
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0494 before and 0.0424 after correction.
The Ratio of minimum to maximum transmission is 0.9254.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0614P)^2^+0.1919P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3202
_reflns_number_total             3842
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra02722d3.cif
_cod_data_source_block           111
_cod_database_code               7245203
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.932
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C12(H12), C14(H14), C13(H13), C4(H4), C6(H6), C3(H3), C7(H7)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              98958
_shelx_hkl_checksum              54711
_olex2_submission_special_instructions 'No special instructions were received'