Cyclocondensation of Arylhydrazines with 1,3-Bis(het)arylmonothio-1,3-diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 1-Aryl-3,5-bis(het)arylpyrazoles with Complementary Regioselectivity
S. Vijay Kumar; Santosh K. Yadav; B. Raghava; B. Saraiah; H. Ila; K. S. Rangappa; Arpan Hazra; Journal of Organic Chemistry 78 (2013) 4960–4973; doi:10.1021/jo400599e

data_4028251
_publ_section_title
;
 Cyclocondensation of Arylhydrazines with
 1,3-Bis(het)arylmonothio-1,3-diketones and
 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of
 1-Aryl-3,5-bis(het)arylpyrazoles with Complementary Regioselectivity
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4960
_journal_page_last               4973
_journal_paper_doi               10.1021/jo400599e
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C23 H18 N4'
_chemical_formula_weight         350.41
_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                72.267(4)
_cell_angle_beta                 69.494(3)
_cell_angle_gamma                71.237(3)
_cell_formula_units_Z            2
_cell_length_a                   9.3639(16)
_cell_length_b                   10.2100(18)
_cell_length_c                   10.8034(18)
_cell_measurement_temperature    293(2)
_cell_volume                     894.3(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6024
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.079
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             368
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0648
_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^)+(0.1419P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1834
_refine_ls_wR_factor_ref         0.2372
_reflns_number_gt                2340
_reflns_number_total             4264
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400599e_si_002_6.cif
_cod_data_source_block           compound9i
_cod_database_code               4028251