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_4029355
_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         'C16 H14 Cl3 N9 S5'
_chemical_formula_sum            'C16 H14 Cl3 N9 S5'
_chemical_formula_weight         599.01
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.143(4)
_cell_angle_beta                 92.352(3)
_cell_angle_gamma                93.441(4)
_cell_formula_units_Z            4
_cell_length_a                   10.4490(4)
_cell_length_b                   12.6255(8)
_cell_length_c                   21.3511(9)
_cell_measurement_reflns_used    4402
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.9700
_cell_measurement_theta_min      3.4020
_cell_volume                     2786.5(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4223
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    0.0956
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20504
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_platon_squeeze_details
;
;
_refine_diff_density_max         1.153
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         9786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1240
_refine_ls_R_factor_gt           0.0824
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1414P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2259
_refine_ls_wR_factor_ref         0.2523
_reflns_number_gt                5674
_reflns_number_total             9786
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500509e_si_004.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               4029355