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_4030067
_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            'C22 H17 Cl N2'
_chemical_formula_weight         344.83
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 107.85(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.469(2)
_cell_length_b                   17.517(4)
_cell_length_c                   9.5531(19)
_cell_measurement_temperature    293(2)
_cell_volume                     1826.9(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13367
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.215
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0000(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.205
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0889
_refine_ls_shift/su_max          0.819
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0677P)^2^+0.9398P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1876
_refine_ls_wR_factor_ref         0.2071
_reflns_number_gt                2765
_reflns_number_total             3542
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501844x_si_003.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 4030067--4030068.cif.'
_cod_original_cell_volume        1826.8(6)
_cod_database_code               4030067