I2-Mediated Oxidative C-N Bond Formation for Metal-Free One-Pot Synthesis of Di-, Tri-, and Tetrasubstituted Pyrazoles from α,β-Unsaturated Aldehydes/Ketones and Hydrazines.
Zhang, Xinting; Kang, Jinfeng; Niu, Pengfei; Wu, Jie; Yu, Wenquan; Chang, Junbiao; The Journal of organic chemistry 79 (2014) 10170–; doi:10.1021/jo501844x

data_4030068
_publ_section_title
;
 I2-Mediated Oxidative C-N Bond Formation for Metal-Free One-Pot Synthesis
 of Di-, Tri-, and Tetrasubstituted Pyrazoles from \a,\b-Unsaturated
 Aldehydes/Ketones and Hydrazines.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10170
_journal_paper_doi               10.1021/jo501844x
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C16 H11 N3'
_chemical_formula_weight         245.28
_space_group_IT_number           2
_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                113.94(3)
_cell_angle_beta                 92.53(3)
_cell_angle_gamma                92.22(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9756(14)
_cell_length_b                   9.910(2)
_cell_length_c                   10.420(2)
_cell_measurement_temperature    293(2)
_cell_volume                     656.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6416
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.076
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0596
_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^)+(0.0776P)^2^+0.0914P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1771
_reflns_number_gt                2390
_reflns_number_total             3049
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501844x_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 4030067--4030068.cif.'
_cod_original_cell_volume        656.4(2)
_cod_database_code               4030068