Silver(I)-Catalyzed Reaction between Pyrazole and Propargyl Acetates: Stereoselective Synthesis of the Scorpionate Ligands (E)-Allyl-gem-dipyrazoles (ADPs)
M. Bhanuchandra; Malleswara Rao Kuram; Akhila K. Sahoo; Journal of Organic Chemistry 78 (2013) 11824–11834; doi:10.1021/jo401867e

data_4028796
_publ_section_title
;
 Silver(I)-Catalyzed Reaction between Pyrazole and Propargyl Acetates:
 Stereoselective Synthesis of the Scorpionate Ligands
 (E)-Allyl-gem-dipyrazoles (ADPs)
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11824
_journal_page_last               11834
_journal_paper_doi               10.1021/jo401867e
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C19 H16 N4'
_chemical_formula_weight         300.02
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 109.76(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   16.904(4)
_cell_length_b                   17.000(4)
_cell_length_c                   17.259(6)
_cell_measurement_temperature    293(2)
_cell_volume                     4668(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.848
_diffrn_measured_fraction_theta_max 0.848
_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  0.1654
_diffrn_reflns_av_sigmaI/netI    0.4352
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20708
_diffrn_reflns_theta_full        29.06
_diffrn_reflns_theta_max         29.06
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.079
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             1892
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.830
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         10588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.4947
_refine_ls_R_factor_gt           0.0937
_refine_ls_shift/su_max          1.919
_refine_ls_shift/su_mean         0.037
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0208P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.2510
_reflns_number_gt                1088
_reflns_number_total             10588
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401867e_si_004.cif
_cod_data_source_block           aks38
_cod_database_code               4028796