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_7225946
_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         'C8 H7 Br N2'
_chemical_formula_sum            'C8 H7 Br N2'
_chemical_formula_weight         211.07
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.622(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.9883(6)
_cell_length_b                   17.853(2)
_cell_length_c                   11.2011(12)
_cell_measurement_reflns_used    1361
_cell_measurement_temperature    120.01(16)
_cell_measurement_theta_max      72.5080
_cell_measurement_theta_min      4.6450
_cell_volume                     797.23(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega   18.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0434  -57.0000  -30.0000 43

  2 omega   20.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0434  -57.0000  -60.0000 28

  3 omega   21.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0434  -62.0000 -129.4610 47

  4 omega   53.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -65.0000 -121.0159 42

  5 omega   59.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -65.0000  -67.6919 47

  6 omega   60.00  136.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -65.0000  -15.1881 76

  7 omega   71.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -64.0000   30.9583 34

  8 omega   67.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -62.0000   65.0330 25

  9 omega   55.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000   90.0000 35

 10 omega   66.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -64.0000  167.3480 40

 11 omega   33.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0434  -57.0000   90.0000 35

 12 omega   25.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0434  -62.0000   65.2653 41

 13 omega   82.00  160.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   30.0000  150.0000 78

 14 omega   42.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -65.0000  116.7107 63

 15 omega   26.00  155.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -15.0000  -60.0000 129

 16 omega   79.00  114.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   30.0000 -120.0000 35

 17 omega   35.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -120.0000 51

 18 omega   37.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -180.0000 52

 19 omega   -1.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0434  -57.0000 -180.0000 66

 20 omega  -47.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0434   37.0000  120.0000 77

 21 omega  -79.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0434   19.0000   60.0000 109
;
_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      0.1804102000
_diffrn_orient_matrix_UB_12      -0.0254331000
_diffrn_orient_matrix_UB_13      0.1165861000
_diffrn_orient_matrix_UB_21      0.3387767000
_diffrn_orient_matrix_UB_22      0.0240636000
_diffrn_orient_matrix_UB_23      -0.0504402000
_diffrn_orient_matrix_UB_31      -0.0455250000
_diffrn_orient_matrix_UB_32      0.0788328000
_diffrn_orient_matrix_UB_33      0.0529177000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4773
_diffrn_reflns_theta_full        74.27
_diffrn_reflns_theta_max         74.27
_diffrn_reflns_theta_min         4.66
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.457
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.0777
_exptl_crystal_size_min          0.0292
_refine_diff_density_max         1.883
_refine_diff_density_min         -1.091
_refine_diff_density_rms         0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1081P)^2^+1.2883P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1730
_refine_ls_wR_factor_ref         0.1847
_reflns_number_gt                1261
_reflns_number_total             1576
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6gc01601d6.cif
_cod_data_source_block           mrc2g
_cod_depositor_comments
'Adding full bibliography for 7225942--7225950.cif.'
_cod_original_cell_volume        797.27(17)
_cod_database_code               7225946
_chemical_oxdiff_formula         'C10 H10 N2 Br1'
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C6(H6), C2(H2)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_olex2_date_sample_data_collection 2016-01-12
_olex2_submission_special_instructions 'No special instructions were received'