Catalyst-free Friedel–Crafts hydroxyalkylation of imidazo[1,2-α]pyridines with ethyl trifluoropyruvate
Li, Ke; Zhao, Xue-Mei; Yang, Fa-Liu; Hou, Xiao-Han; Xu, Yan; Guo, Yan-Chun; Hao, Xin-Qi; Song, Mao-Ping; RSC Advances 5 (2015) 90478–; doi:10.1039/C5RA15678E

data_7235957
_publ_section_title
;
 Catalyst-free Friedel--Crafts hydroxyalkylation of
 imidazo[1,2-\a]pyridines with ethyl trifluoropyruvate
;
_journal_issue                   110
_journal_name_full               'RSC Advances'
_journal_page_first              90478
_journal_paper_doi               10.1039/C5RA15678E
_journal_volume                  5
_journal_year                    2015
_chemical_formula_moiety         'C18 H15 F3 N2 O3, C2 H6 O'
_chemical_formula_sum            'C20 H21 F3 N2 O4'
_chemical_formula_weight         410.39
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-31
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-07-02 deposited with the CCDC.
2015-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.876(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8633(5)
_cell_length_b                   12.9671(4)
_cell_length_c                   14.6615(5)
_cell_measurement_reflns_used    3422
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.1720
_cell_measurement_theta_min      4.6170
_cell_volume                     1996.08(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   16.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -30.0000 26

  2 omega   -7.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000   30.0000 32

  3 omega   -1.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   60.0000 37

  4 omega  -67.00  -30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000   30.0000 37

  5 omega   77.00  121.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000   30.0000 44

  6 omega   45.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -90.0000 37

  7 omega  -16.00   79.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -37.0000  120.0000 95

  8 omega   45.00  108.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000 -150.0000 63

  9 omega   46.00  125.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -60.0000 79

 10 omega   58.00   90.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 32

 11 omega   74.00  107.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   90.0000 33

 12 omega   57.00   84.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 27

 13 omega   42.00   93.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 51

 14 omega   97.00  178.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  -30.0000 81

 15 omega  105.00  178.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   30.0000 73

 16 omega   58.00  108.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -180.0000 50

 17 omega   42.00   98.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  150.0000 56

 18 omega  121.00  178.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000   30.0000 57

 19 omega  -26.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000   30.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0591419000
_diffrn_orient_matrix_UB_12      0.1011368000
_diffrn_orient_matrix_UB_13      0.0242340000
_diffrn_orient_matrix_UB_21      0.1227202000
_diffrn_orient_matrix_UB_22      0.0584819000
_diffrn_orient_matrix_UB_23      -0.0022436000
_diffrn_orient_matrix_UB_31      -0.0548059000
_diffrn_orient_matrix_UB_32      0.0218448000
_diffrn_orient_matrix_UB_33      -0.1059869000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7321
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.026
_diffrn_reflns_theta_max         67.026
_diffrn_reflns_theta_min         4.211
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.975
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0042(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3560
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0550P)^2^+0.3758P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1139
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3001
_reflns_number_total             3560
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra15678e2.cif
_cod_data_source_block           20150351
_cod_original_cell_volume        1996.08(13)
_cod_database_code               7235957
_chemical_oxdiff_formula         C20H20N4O5F3
_shelx_estimated_absorpt_t_max   0.844
_shelx_estimated_absorpt_t_min   0.829
_reflns_odcompleteness_completeness 100.00
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C20-C19
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C19) = Uanis(C19A)
Uanis(C20) = Uanis(C20A)
4. Others
 Sof(H4B)=Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20D)=Sof(H20E)=
 Sof(H20F)=1-FVAR(1)
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(H4A)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C19A(H19C,H19D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
5.c Tetrahedral OH refined with riding coordinates:
 O4(H4A), O4(H4B)
5.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F)
;
_shelx_res_checksum              49877
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'