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_7152179
_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         'C7 H12 N2 S1'
_chemical_formula_sum            'C7 H12 N2 S'
_chemical_formula_weight         156.25
_chemical_melting_point          338.0(10)
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 94.763(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1350(2)
_cell_length_b                   10.7533(6)
_cell_length_c                   15.1732(8)
_cell_measurement_reflns_used    1847
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     834.94(7)
_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 0.985
_diffrn_measured_fraction_theta_max 0.976
_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  0.036
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7213
_diffrn_reflns_theta_full        25.589
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_min         5.341
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.64
_refine_diff_density_min         -0.51
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0810
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1884
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.0003780
_refine_ls_shift/su_mean         0.0000236
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.09P)^2^ + 1.15P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1829
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1829
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                1516
_reflns_number_total             1888
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.62
_oxford_diffrn_Wilson_scale      1.11
_oxford_refine_ls_r_factor_ref   0.0790
_oxford_refine_ls_scale          0.956(9)
_oxford_reflns_number_all        1884
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title '4011001 037aki10'
_cod_data_source_file            c1ob06587d.txt
_cod_data_source_block           3o
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '337 - 339' was changed to
'338.0(10)' - the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' 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_H-M      'P 1 21/a 1 '
_cod_original_formula_sum        'C7 H12 N2 S1'
_cod_database_code               7152179
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S
RIDE N ( 6,X'S) H ( 62,X'S) H ( 61,X'S)
RIDE C ( 7,X'S) H ( 71,X'S) H ( 73,X'S) H ( 72,X'S)
RIDE C ( 8,X'S) H ( 81,X'S)
RIDE C ( 9,X'S) H ( 92,X'S) H ( 91,X'S) H ( 93,X'S)
RIDE C ( 10,X'S) H ( 102,X'S) H ( 101,X'S) H ( 103,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
;