Catalyst-Free Synthesis of 2,4-Disubstituted-1<i>H</i>-imidazoles through [3 + 2] Cyclization of Vinyl Azides with Amidines.
Reddy, N. Naresh Kumar; Nageswara Rao, Sadu; Ravi, Chitrakar; Adimurthy, Subbarayappa; ACS omega 2 (2017) 5235–5241; doi:10.1021/acsomega.7b00969

data_4516912
_publ_section_title
;
 Catalyst-Free Synthesis of 2,4-Disubstituted-1<i>H</i>-imidazoles through
 [3 + 2] Cyclization of Vinyl Azides with Amidines.
;
_journal_issue                   8
_journal_name_full               'ACS omega'
_journal_page_first              5235
_journal_page_last               5241
_journal_paper_doi               10.1021/acsomega.7b00969
_journal_volume                  2
_journal_year                    2017
_chemical_formula_sum            'C15 H11 Br N2'
_chemical_formula_weight         299.17
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.281(3)
_cell_length_b                   27.212(8)
_cell_length_c                   5.4812(16)
_cell_measurement_reflns_used    1056
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.08
_cell_measurement_theta_min      2.86
_cell_volume                     1235.1(7)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFARCTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_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  0.0820
_diffrn_reflns_av_sigmaI/netI    0.0984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6237
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    3.309
_exptl_absorpt_correction_T_max  0.9368
_exptl_absorpt_correction_T_min  0.3370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATES
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2188
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0666P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1334
_reflns_number_gt                1513
_reflns_number_total             2188
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao7b00969_si_002.cif
_cod_data_source_block           nr113f
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' 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.

data item '_symmetry_cell_setting' value 'ORTHORHOMBIC' was changed
to 'orthorhombic' 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 
;
_cod_original_cell_volume        1235.1(6)
_cod_original_sg_symbol_H-M      Pna21
_cod_database_code               4516912