N-chlorosuccinimide-promoted regioselective sulfenylation of imidazoheterocycles at room temperature.
Ravi, Chitrakar; Chandra Mohan, Darapaneni; Adimurthy, Subbarayappa; Organic letters 16 (2014) 2978–2981; doi:10.1021/ol501117z

data_1516132
_publ_section_title
;
 N-chlorosuccinimide-promoted regioselective sulfenylation of
 imidazoheterocycles at room temperature.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2978
_journal_page_last               2981
_journal_paper_doi               10.1021/ol501117z
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C19 H14 Br N2 O0.5 S'
_chemical_formula_weight         390.29
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 104.457(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.406(2)
_cell_length_b                   14.522(3)
_cell_length_c                   20.970(4)
_cell_measurement_temperature    293(2)
_cell_volume                     3363.4(11)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9618
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    2.572
_exptl_absorpt_correction_T_max  0.6989
_exptl_absorpt_correction_T_min  0.4260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            'PALE YELLOW'
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCKS
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.530
_refine_diff_density_min         -1.050
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0532P)^2^+2.1282P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                2936
_reflns_number_total             3674
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501117z_si_002.cif
_cod_data_source_block           adi13m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1516132.cif.
;
_cod_original_cell_volume        3363.4(12)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C19 H14 Br N2 O0.50 S'
_cod_database_code               1516132