Reinvestigating the Reaction of 1H-Pyrazol-5-amines with 4,5-Dichloro-1,2,3-dithiazolium Chloride: A Route to Pyrazolo[3,4-c]isothiazoles and Pyrazolo[3,4-d]thiazoles.
Koyioni, Maria; Manoli, Maria; Manolis, Manos J.; Koutentis, Panayiotis A.; The Journal of organic chemistry 79 (2014) 4025–4037; doi:10.1021/jo500509e

data_4029354
_publ_section_title
;
 Reinvestigating the Reaction of 1H-Pyrazol-5-amines with
 4,5-Dichloro-1,2,3-dithiazolium Chloride: A Route to
 Pyrazolo[3,4-c]isothiazoles and Pyrazolo[3,4-d]thiazoles.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4025
_journal_page_last               4037
_journal_paper_doi               10.1021/jo500509e
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C14 H12 Cl2 N8 S5'
_chemical_formula_sum            'C14 H12 Cl2 N8 S5'
_chemical_formula_weight         523.57
_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                 100.148(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   34.721(5)
_cell_length_b                   4.0036(5)
_cell_length_c                   14.975(2)
_cell_measurement_reflns_used    2111
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.5990
_cell_measurement_theta_min      2.9208
_cell_volume                     2049.1(5)
_computing_cell_refinement       'CrysAlis RED'
_computing_data_collection       'CrysAlis CCD'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics
;
 DIAMOND (Brandenburg, 2006)
 MERCURY (Bruno et al. 2002)
;
_computing_publication_material  'WINGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4223
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4564
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         3.20
_exptl_absorpt_coefficient_mu    0.847
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.880
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0623
_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^)+(0.1335P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1725
_refine_ls_wR_factor_ref         0.1812
_reflns_number_gt                1677
_reflns_number_total             2101
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500509e_si_003.cif
_cod_data_source_block           shelxl
_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.

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

 Adding full bibliography for 4029353--4029355.cif.
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4029354