Oxidative sulfonamidomethylation of imidazopyridines utilizing methanol as the main C1 source.
Zhao, Xue-Mei; Huang, En-Ling; Zhu, Yu-Shen; Li, Jing; Song, Bing; Zhu, Xinju; Hao, Xin-Qi; Organic & biomolecular chemistry 17 (2019) 4869–4878; doi:10.1039/c9ob00596j

data_7156781
_publ_section_title
;
 Oxidative sulfonamidomethylation of imidazopyridines utilizing methanol
 as the main C1 source.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4869
_journal_page_last               4878
_journal_paper_doi               10.1039/c9ob00596j
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C20 H17 N3 O2 S'
_chemical_formula_sum            'C20 H17 N3 O2 S'
_chemical_formula_weight         363.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-06-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-30 deposited with the CCDC.    2019-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.311(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3160(2)
_cell_length_b                   19.1755(5)
_cell_length_c                   12.7269(5)
_cell_measurement_reflns_used    2613
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8000
_cell_measurement_theta_min      3.5630
_cell_volume                     1737.46(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -40.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -150.0000 60

  2 omega  -50.00  -25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  -30.0000 25

  3 omega  -17.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  -30.0000 50

  4 omega   66.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 41

  5 omega   31.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 39

  6 omega   28.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -150.0000 78

  7 omega    9.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 47

  8 omega   21.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 49

  9 omega   59.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 26

 10 omega   51.00   77.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 26

 11 omega   37.00   83.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 46

 12 omega   89.00  174.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 85

 13 omega   38.00  108.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 14 omega  100.00  178.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  127.0000  111.0000 78

 15 omega   55.00  127.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -180.0000 72

 16 omega   48.00  103.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 55

 17 omega   85.00  167.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0258440000
_diffrn_orient_matrix_UB_12      0.0223496000
_diffrn_orient_matrix_UB_13      -0.1187152000
_diffrn_orient_matrix_UB_21      0.0187373000
_diffrn_orient_matrix_UB_22      0.0770467000
_diffrn_orient_matrix_UB_23      0.0352300000
_diffrn_orient_matrix_UB_31      0.2141454000
_diffrn_orient_matrix_UB_32      -0.0040752000
_diffrn_orient_matrix_UB_33      0.0116550000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6661
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.250
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.820
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0913
_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^)+(0.0351P)^2^+7.0645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1988
_refine_ls_wR_factor_ref         0.2019
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2795
_reflns_number_total             3094
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00596j2.cif
_cod_data_source_block           201806282
_cod_depositor_comments          'Adding full bibliography for 7156781.cif.'
_cod_original_cell_volume        1737.47(10)
_cod_database_code               7156781
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N1S1
_shelx_estimated_absorpt_t_max   0.798
_shelx_estimated_absorpt_t_min   0.735
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C14A-C6A
 1.55 with sigma of 0.02
 N3A-C14A
 1.45 with sigma of 0.02
 S1-N3A
 1.65 with sigma of 0.02
 C1A-C2A
 1.39 with sigma of 0.02
 C2A-C3A
 1.39 with sigma of 0.02
 C5A-C4A
 1.39 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(N1A)
Uanis(C6) = Uanis(C6A)
Uanis(N2) = Uanis(N2A)
Uanis(C5) = Uanis(C5A)
Uanis(C7) = Uanis(C7A)
Uanis(C1) = Uanis(C1A)
Uanis(C2) = Uanis(C2A)
Uanis(C3) = Uanis(C3A)
Uanis(C4) = Uanis(C4A)
Uanis(C8) = Uanis(C8A)
Uanis(C13) = Uanis(C13A)
Uanis(C12) = Uanis(C12A)
Uanis(C11) = Uanis(C11A)
Uanis(C10) = Uanis(C10A)
Uanis(C9) = Uanis(C9A)
Uanis(C14) = Uanis(C14A)
Uanis(N3) = Uanis(N3A)
4. Others
 Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=
 Sof(C5A)=Sof(C6A)=Sof(C7A)=Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=
 Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=
 Sof(H14C)=Sof(H14D)=Sof(N1A)=Sof(N2A)=Sof(N3A)=Sof(H3AA)=1-FVAR(1)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=
 Sof(C6)=Sof(C7)=Sof(C8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=
 Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(N1)=
 Sof(N2)=Sof(N3)=Sof(H3B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14A(H14C,H14D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C1A(H1A), C2(H2), C2A(H2A), C3(H3), C3A(H3A), C4(H4), C4A(H4A),
 C9(H9), C9A(H9A), C10(H10), C10A(H10A), C11(H11), C11A(H11A), C12(H12),
 C12A(H12A), C13(H13), C13A(H13A), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), N3(H3B), N3A(H3AA)
;
_olex2_submission_special_instructions 'No special instructions were received'