Direct preparation of thiazoles, imidazoles, imidazopyridines and thiazolidines from alkenes.
Donohoe, Timothy J.; Kabeshov, Mikhail A.; Rathi, Akshat H.; Smith, Ian E. D.; Organic & biomolecular chemistry 10 (2012) 1093–1101; doi:10.1039/c1ob06587d

data_7152177
_publ_section_title
;
 Direct preparation of thiazoles, imidazoles, imidazopyridines and
 thiazolidines from alkenes.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1093
_journal_page_last               1101
_journal_paper_doi               10.1039/c1ob06587d
_journal_volume                  10
_journal_year                    2012
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C13 H9 Br1 N2'
_chemical_formula_sum            'C13 H9 Br N2'
_chemical_formula_weight         273.13
_chemical_melting_point          467.0(10)
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.55110(10)
_cell_length_b                   15.6885(3)
_cell_length_c                   25.0161(7)
_cell_measurement_reflns_used    2439
_cell_measurement_temperature    150
_cell_measurement_theta_max      28
_cell_measurement_theta_min      5
_cell_volume                     2178.61(8)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12609
_diffrn_reflns_theta_full        25.910
_diffrn_reflns_theta_max         27.860
_diffrn_reflns_theta_min         5.419
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.743
_exptl_absorpt_correction_T_max  0.69
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.07
_refine_diff_density_min         -1.10
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9956
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2530
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0646
_refine_ls_shift/su_max          0.0007530
_refine_ls_shift/su_mean         0.0000419
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.06P)^2^ +14.99P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1802
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1799
_reflns_limit_h_max              7
_reflns_limit_h_min              0
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              32
_reflns_limit_l_min              0
_reflns_number_gt                1912
_reflns_number_total             2534
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.61
_oxford_diffrn_Wilson_scale      3.95
_oxford_refine_ls_r_factor_ref   0.0874
_oxford_refine_ls_scale          0.532(2)
_oxford_reflns_number_all        2532
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title '3091513 034aki10'
_cod_data_source_file            c1ob06587d.txt
_cod_data_source_block           7c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '466 - 468' was changed to
'467.0(10)' - the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P b c a '
_cod_original_formula_sum        'C13 H9 Br1 N2'
_cod_database_code               7152177
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S
RIDE C ( 3,X'S) H ( 31,X'S)
RIDE C ( 8,X'S) H ( 81,X'S)
RIDE C ( 10,X'S) H ( 101,X'S)
RIDE C ( 11,X'S) H ( 111,X'S)
RIDE C ( 12,X'S) H ( 121,X'S)
RIDE C ( 13,X'S) H ( 131,X'S)
RIDE C ( 14,X'S) H ( 141,X'S)
RIDE C ( 15,X'S) H ( 151,X'S)
RIDE C ( 16,X'S) H ( 161,X'S)
END
;
_iucr_refine_instruction_details_restraints
;
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;