Transition-Metal-Free Tandem Chlorocyclization of Amines with Carboxylic Acids: Access to Chloroimidazo[1,2-α]pyridines.
Xiao, Xinsheng; Xie, Ying; Bai, Siyi; Deng, Yuanfu; Jiang, Huanfeng; Zeng, Wei; Organic letters 17 (2015) 3998–4001; doi:10.1021/acs.orglett.5b01868

data_1555154
_publ_section_title
;
 Transition-Metal-Free Tandem Chlorocyclization of Amines with Carboxylic
 Acids: Access to Chloroimidazo[1,2-\a]pyridines.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3998
_journal_page_last               4001
_journal_paper_doi               10.1021/acs.orglett.5b01868
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C14 H11 Cl N2'
_chemical_formula_weight         242.70
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.208(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.4081(5)
_cell_length_b                   7.7461(3)
_cell_length_c                   19.9246(6)
_cell_measurement_temperature    571(2)
_cell_measurement_theta_max      62.61
_cell_measurement_theta_min      3.40
_cell_volume                     2353.69(14)
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAIRT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      571(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9876
_diffrn_reflns_theta_full        62.61
_diffrn_reflns_theta_max         62.61
_diffrn_reflns_theta_min         3.40
_exptl_absorpt_coefficient_mu    2.669
_exptl_absorpt_correction_T_max  0.6748
_exptl_absorpt_correction_T_min  0.5668
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plane
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0522
_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^)+(0.1049P)^2^+0.3032P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1562
_reflns_number_gt                3234
_reflns_number_total             3726
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01868_si_005.cif
_cod_data_source_block           sad
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 

2022-05-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_original_formula_sum        'C28 H22 Cl2 N4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     485.40
_cod_database_code               1555154