Rapid, metal-free and aqueous synthesis of imidazo[1,2-a]pyridine under ambient conditions
Chapman, Michael R.; Kwan, Maria H. T.; King, Georgina E.; Kyffin, Benjamin A.; Blacker, A. John; Willans, Charlotte E.; Nguyen, Bao N.; Green Chem. 18 (2016) 4623–; doi:10.1039/C6GC01601D

data_7225948
_publ_section_title
;
 Rapid, metal-free and aqueous synthesis of imidazo[1,2-a]pyridine under
 ambient conditions
;
_journal_issue                   17
_journal_name_full               'Green Chem.'
_journal_page_first              4623
_journal_paper_doi               10.1039/C6GC01601D
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'Br, C12 H11 Cl F3 N2'
_chemical_formula_sum            'C12 H11 Br Cl F3 N2'
_chemical_formula_weight         355.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                98.874(9)
_cell_angle_beta                 103.353(9)
_cell_angle_gamma                103.781(9)
_cell_formula_units_Z            4
_cell_length_a                   11.0563(12)
_cell_length_b                   11.1805(12)
_cell_length_c                   12.0711(12)
_cell_measurement_reflns_used    2531
_cell_measurement_temperature    120.00(11)
_cell_measurement_theta_max      25.0900
_cell_measurement_theta_min      3.0750
_cell_volume                     1375.0(3)
_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, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.862
_diffrn_measurement_details
;
  1 omega  -33.00   -6.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509  -37.0000   60.0000 27

  2 omega   30.00   78.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   37.0000   90.0000 48

  3 omega   15.00   75.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   57.0000  -60.0000 60

  4 omega   -9.00   76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   57.0000   28.0000 85

  5 omega    2.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   57.0000  150.0000 79

  6 omega  -11.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   57.0000 -120.0000 80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0243131000
_diffrn_orient_matrix_UB_12      0.0423816000
_diffrn_orient_matrix_UB_13      -0.0307142000
_diffrn_orient_matrix_UB_21      -0.0494501000
_diffrn_orient_matrix_UB_22      -0.0043436000
_diffrn_orient_matrix_UB_23      0.0288530000
_diffrn_orient_matrix_UB_31      0.0411708000
_diffrn_orient_matrix_UB_32      0.0516897000
_diffrn_orient_matrix_UB_33      0.0453822000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0930
_diffrn_reflns_av_unetI/netI     0.1708
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15553
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.21
_diffrn_reflns_theta_min         2.89
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.205
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95974
_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_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.2673
_exptl_crystal_size_mid          0.1112
_exptl_crystal_size_min          0.0797
_refine_diff_density_max         2.020
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         7696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1488
_refine_ls_R_factor_gt           0.0758
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0205P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1500
_reflns_number_gt                4341
_reflns_number_total             7696
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6gc01601d10.cif
_cod_data_source_block           mrc213
_cod_depositor_comments
'Adding full bibliography for 7225942--7225950.cif.'
_cod_original_cell_volume        1375.0(2)
_cod_database_code               7225948
_chemical_oxdiff_formula         'C48 H36 Br4 Cl4 F12 N8'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C15(H15), C23(H23), C19(H19), C20(H20), C8(H8), C3(H3), C11(H11)
2.c X=CH2 refined with riding coordinates:
 C4(H4A,H4B), C16(H16A,H16B)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C18(H18A,H18B,H18C)
;
_olex2_date_sample_data_collection 2015-05-06
_olex2_submission_special_instructions 'No special instructions were received'