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_7225942
_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, C16 H13 Cl F3 N2'
_chemical_formula_sum            'C16 H13 Br Cl F3 N2'
_chemical_formula_weight         405.64
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 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                90.00
_cell_angle_beta                 104.181(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   22.7475(15)
_cell_length_b                   11.3014(7)
_cell_length_c                   27.0251(16)
_cell_measurement_reflns_used    5705
_cell_measurement_temperature    120.02(16)
_cell_measurement_theta_max      29.6100
_cell_measurement_theta_min      3.1630
_cell_volume                     6735.9(7)
_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      120.02(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_details
;
  1 omega   -6.00   42.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   37.0000  -60.0000 48

  2 omega  -20.00   15.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   19.0000 -180.0000 35

  3 omega   45.00   81.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   19.0000 -180.0000 36

  4 omega  -40.00   31.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509  -57.0000  -90.0000 71

  5 omega  -24.00    3.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9509  -57.0000   90.0000 27

  6 omega  -67.00  -15.00   1.0000  160.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.7322  -57.0000  150.0000 52
;
_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      0.0231324000
_diffrn_orient_matrix_UB_12      0.0302730000
_diffrn_orient_matrix_UB_13      0.0179196000
_diffrn_orient_matrix_UB_21      -0.0042132000
_diffrn_orient_matrix_UB_22      0.0502924000
_diffrn_orient_matrix_UB_23      -0.0161575000
_diffrn_orient_matrix_UB_31      -0.0219407000
_diffrn_orient_matrix_UB_32      0.0222386000
_diffrn_orient_matrix_UB_33      0.0122658000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0993
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            26483
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.15
_diffrn_reflns_theta_min         2.69
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87871
_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    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3232
_exptl_crystal_size_max          0.1218
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.0505
_refine_diff_density_max         1.643
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         9663
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0660
_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^)+(0.0388P)^2^+21.8616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1368
_reflns_number_gt                6381
_reflns_number_total             9663
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6gc01601d9.cif
_cod_data_source_block           mrc227
_cod_depositor_comments
'Adding full bibliography for 7225942--7225950.cif.'
_cod_original_cell_volume        6735.8(7)
_cod_database_code               7225942
_chemical_oxdiff_formula         'C256 H208 Br16 Cl16 F48 N32'
_reflns_odcompleteness_completeness 99.78
_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. Uiso/Uaniso restraints and constraints
F4 \\sim F5 \\sim F6 \\sim F7 \\sim F8 \\sim F9: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
Uanis(F9) = Uanis(F4) = Uanis(F5) = Uanis(F6) = Uanis(F7) = Uanis(F8)
3. Others
 Fixed Sof: F5(0.5) F7(0.5) F9(0.5) F8(0.5) F6(0.5) F4(0.5)
4.a Riding coordinates:
 C32(H32)
4.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C10(H10A,H10B)
4.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C14(H14), C5(H5), C15(H15), C30(H30), C7(H7), C3(H3),
 C16(H16), C19(H19), C23(H23), C22(H22), C29(H29), C28(H28), C31(H31)
4.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C25(H25A,H25B,H25C)
;
_olex2_date_sample_data_collection 2015-05-06
_olex2_submission_special_instructions 'No special instructions were received'