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_7225947
_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 H8 I N2, Br'
_chemical_formula_sum            'C8 H8 Br I N2'
_chemical_formula_weight         338.97
_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                 103.295(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0553(4)
_cell_length_b                   14.8323(10)
_cell_length_c                   12.4390(10)
_cell_measurement_reflns_used    2422
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5210
_cell_measurement_theta_min      3.4470
_cell_volume                     1087.25(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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_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 0.863
_diffrn_measurement_details
;
  1 omega    9.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   37.0000  -60.0000 60

  2 omega   -5.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509  -57.0000  -90.0000 40

  3 omega  -40.00    1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.7322  -57.0000  150.0000 41

  4 omega  -32.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.7322   37.0000  150.0000 71
;
_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      0.0315509000
_diffrn_orient_matrix_UB_12      0.0271133000
_diffrn_orient_matrix_UB_13      0.0480656000
_diffrn_orient_matrix_UB_21      0.0045048000
_diffrn_orient_matrix_UB_22      0.0383670000
_diffrn_orient_matrix_UB_23      -0.0334220000
_diffrn_orient_matrix_UB_31      -0.1160498000
_diffrn_orient_matrix_UB_32      0.0088473000
_diffrn_orient_matrix_UB_33      -0.0021642000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6777
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.25
_diffrn_reflns_theta_min         3.22
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77506
_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 orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.071
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.2118
_exptl_crystal_size_mid          0.1382
_exptl_crystal_size_min          0.0712
_refine_diff_density_max         1.256
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         3055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0199P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0781
_reflns_number_gt                2337
_reflns_number_total             3055
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6gc01601d4.cif
_cod_data_source_block           mrc214
_cod_depositor_comments
'Adding full bibliography for 7225942--7225950.cif.'
_cod_original_cell_volume        1087.24(14)
_cod_database_code               7225947
_chemical_oxdiff_formula         'C32 H32 Br4 I4 N8'
_reflns_odcompleteness_completeness 99.86
_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, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.d :
 C8(H8)
;
_olex2_date_sample_data_collection 2016-01-10
_olex2_submission_special_instructions 'No special instructions were received'