Structure-Selectivity Relationship in Ruthenium-Catalyzed Regio- and Stereoselective Addition of Alkynes to Pyrazoles: An Experimental and Theoretical Investigation.
Das, Uttam Kumar; Mandal, Subhajit; Anoop, Anakuthil; Bhattacharjee, Manish; The Journal of organic chemistry 79 (2014) 9979–; doi:10.1021/jo502151z

data_4030110
_publ_section_title
;
 Structure-Selectivity Relationship in Ruthenium-Catalyzed Regio- and
 Stereoselective Addition of Alkynes to Pyrazoles: An Experimental and
 Theoretical Investigation.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9979
_journal_paper_doi               10.1021/jo502151z
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C21 H17 N3 O2'
_chemical_formula_weight         343.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 109.457(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.321(10)
_cell_length_b                   7.322(4)
_cell_length_c                   14.433(8)
_cell_measurement_temperature    293(2)
_cell_volume                     1825.6(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.1529
_diffrn_reflns_av_sigmaI/netI    0.1063
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20581
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.18
_exptl_absorpt_coefficient_mu    0.082
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.039(4)
_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   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.2009
_refine_ls_R_factor_gt           0.0760
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0958P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.2237
_reflns_number_gt                1391
_reflns_number_total             3219
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502151z_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 4030110.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4030110