PIDA-Mediated 1,2-ipso-Migration in Mannich Bases of Imidazo[1,2-a]pyridines: Preparation of N-Acetoxymethyl/ Alkoxymethyl-N-arylimidazo[1,2-a]pyridine-3-amines.
Patel, Om P. S.; Jaspal, Sonam; Shinde, Vikki N.; Nandwana, Nitesh Kumar; Rangan, Krishnan; Kumar, Anil; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00674

data_4038425
_publ_section_title
;
 PIDA-Mediated 1,2-ipso-Migration in Mannich Bases of
 Imidazo[1,2-a]pyridines: Preparation of N-Acetoxymethyl/
 Alkoxymethyl-N-arylimidazo[1,2-a]pyridine-3-amines.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00674
_journal_year                    2020
_chemical_formula_moiety         'C20 H17 N3 O'
_chemical_formula_sum            'C20 H17 N3 O'
_chemical_formula_weight         315.36
_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             2020-02-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.6840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.0780(2)
_cell_length_b                   17.8116(2)
_cell_length_c                   13.6505(2)
_cell_measurement_reflns_used    10135
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.5460
_cell_measurement_theta_min      4.1590
_cell_volume                     3143.30(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_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      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -23.00   5.00   0.50    2.14    --    0.00 -77.00-180.00   56
  2  \w    -57.00  19.00   0.50    2.14    --    0.00 -37.00-180.00  152
  3  \w    -87.00 -61.00   0.50    2.14    --    0.00 -37.00 -90.00   52
  4  \w    -88.00 -37.00   0.50    2.14    --    0.00 -77.00-180.00  102
  5  \w    -13.00  13.00   0.50    2.14    --    0.00  37.00   0.00   52
  6  \w    -33.00   9.00   0.50    2.14    --    0.00 -37.00 -90.00   84
  7  \w     27.00 113.00   0.50    8.58    --  107.20 -82.00 -30.00  172
  8  \w     44.00 131.00   0.50    8.58    --  107.20 -61.00  30.00  174
  9  \w     54.00 136.00   0.50    8.58    --  107.20 -82.00  30.00  164
 10  \w    142.00 197.00   0.50    8.58    --  107.20  45.00-180.00  110
 11  \w     31.00  57.00   0.50    8.58    --  107.20 -82.00  90.00   52
 12  \w     87.00 112.00   0.50    8.58    --  107.20 -82.00  90.00   50
 13  \w     88.00 123.00   0.50    8.58    --  107.20  45.00-180.00   70
 14  \w     83.00 181.00   0.50    8.58    --  107.20  61.00 150.00  196
 15  \w     71.00 111.00   0.50    8.58    --  107.20 -82.00 -60.00   80
 16  \w    133.00 189.00   0.50    8.58    --  107.20  30.00-120.00  112
 17  \w     23.00  49.00   0.50    8.58    --  107.20 -82.00  30.00   52
 18  \w     18.00 134.00   0.50    8.58    --  107.20 -15.00-180.00  232
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0877175000
_diffrn_orient_matrix_UB_12      -0.0193964000
_diffrn_orient_matrix_UB_13      -0.0846967000
_diffrn_orient_matrix_UB_21      0.0184002000
_diffrn_orient_matrix_UB_22      -0.0842346000
_diffrn_orient_matrix_UB_23      0.0215657000
_diffrn_orient_matrix_UB_31      -0.0786771000
_diffrn_orient_matrix_UB_32      0.0021486000
_diffrn_orient_matrix_UB_33      0.0733641000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22372
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.793
_diffrn_reflns_theta_min         4.110
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         6664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0386P)^2^+2.4710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5878
_reflns_number_total             6664
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00674_si_004.cif
_cod_data_source_block           exp_566_ak_sj-190-(b)
_cod_database_code               4038425
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_usercomment     BLOCK
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20C,H20D), C20'(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C19(H19), C15(H15), C19'(H19'), C5(H5), C2'(H2'), C12(H12),
 C15'(H15'), C5'(H5'), C9(H9), C2(H2), C18(H18), C13(H13), C3(H3), C16'(H16'),
 C10(H10), C18'(H18'), C11(H11), C9'(H9'), C4'(H4'), C12'(H12'), C17'(H17'),
 C16(H16), C17(H17), C3'(H3'), C13'(H13'), C10'(H10'), C11'(H11')
2.c Idealised tetrahedral OH refined as rotating group:
 O1'(H1'), O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.555
_oxdiff_exptl_absorpt_empirical_full_min 0.675