Synthesis of imidazo[1,2-a]pyridines from unactivated 2-alkyl-4,5-dihydroimidazoles through conjugate N-addition
Jones, Raymond C. F.; Dimopoulos, Paschalis; Coles, Simon C.; Light, Mark E.; Hursthouse, Michael B.; Journal of the Chemical Society, Perkin Transactions 1  (2000) 2331–; doi:10.1039/b001830i

data_7213306
_publ_section_title
;
 Synthesis of imidazo[1,2-a]pyridines from unactivated
 2-alkyl-4,5-dihydroimidazoles through conjugate N-addition
;
_journal_issue                   15
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2331
_journal_paper_doi               10.1039/b001830i
_journal_year                    2000
_chemical_formula_sum            'C25 H28 N2 O4'
_chemical_formula_weight         420.49
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                65.331(3)
_cell_angle_beta                 65.329(4)
_cell_angle_gamma                62.908(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0117(5)
_cell_length_b                   10.6661(8)
_cell_length_c                   12.2753(9)
_cell_measurement_reflns_used    na
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      na
_cell_measurement_theta_min      na
_cell_volume                     1119.42(13)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
;
 ?
;
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean '9.091 pixels/mm'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_av_sigmaI/netI    0.1198
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8067
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         3.26
_diffrn_standards_decay_%        na
_diffrn_standards_interval_count na
_diffrn_standards_interval_time  na
_diffrn_standards_number         'not measured'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9916
_exptl_absorpt_correction_type   'Empirical, SORTAV'
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.931
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0480P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1373
_reflns_number_gt                1568
_reflns_number_total             3169
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b001830isup1.cif
_cod_data_source_block           s92-3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7213306