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_7225945
_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, C9 H11 N2'
_chemical_formula_sum            'C9 H11 Br N2'
_chemical_formula_weight         227.11
_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             2015-11-06
_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                 94.547(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4282(7)
_cell_length_b                   14.9520(14)
_cell_length_c                   8.9188(7)
_cell_measurement_reflns_used    1175
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      71.0100
_cell_measurement_theta_min      5.8110
_cell_volume                     987.46(15)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
  1 omega   23.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.7089   37.0000   30.0000 27

  2 omega   68.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.7089   37.0000   30.0000 27

  3 omega   39.00   97.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000  -60.0000 58

  4 omega   67.00  172.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000 -150.0000 105

  5 omega   62.00  125.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -64.0000   86.7494 63

  6 omega   90.00  127.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  120.0000 37

  7 omega   46.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000    0.0000 38

  8 omega   45.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -64.0000   53.5658 58

  9 omega   43.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   60.0000 27

 10 omega   53.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000 -120.0000 33

 11 omega  -57.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000 -180.0000 87

 12 omega  -61.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000   30.0000 45

 13 omega -107.00  -64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000   30.0000 43
;
_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      0.0207461000
_diffrn_orient_matrix_UB_12      -0.0781117000
_diffrn_orient_matrix_UB_13      -0.1099722000
_diffrn_orient_matrix_UB_21      0.1146728000
_diffrn_orient_matrix_UB_22      0.0598470000
_diffrn_orient_matrix_UB_23      -0.0959923000
_diffrn_orient_matrix_UB_31      0.1722759000
_diffrn_orient_matrix_UB_32      -0.0304392000
_diffrn_orient_matrix_UB_33      0.0935294000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3789
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         74.24
_diffrn_reflns_theta_min         5.79
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82257
_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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2292
_exptl_crystal_size_mid          0.0982
_exptl_crystal_size_min          0.0286
_refine_diff_density_max         1.320
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0686
_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^)+(0.1032P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1740
_refine_ls_wR_factor_ref         0.1896
_reflns_number_gt                1534
_reflns_number_total             1930
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6gc01601d3.cif
_cod_data_source_block           mrc278
_cod_depositor_comments
'Adding full bibliography for 7225942--7225950.cif.'
_cod_original_cell_volume        987.45(15)
_cod_database_code               7225945
_chemical_oxdiff_formula         'C10 H10 N2 Br1'
_reflns_odcompleteness_completeness 99.40
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C2(H2)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
2.e :
 C9(H9)
;
_olex2_date_sample_data_collection 2015-08-26
_olex2_submission_special_instructions 'No special instructions were received'