Multicomponent Pyrazole Synthesis from Alkynes, Nitriles, and Ti Imidos via Oxidatively Induced N-N Bond Coupling.
Pearce, Adam J.; Harkins, Robin P.; Reiner, Benjamin R.; Wotal, Alexander C.; Dunscomb, Rachel J.; Tonks, Ian A.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b13173

data_4134214
_publ_section_title
;
 Multicomponent Pyrazole Synthesis from Alkynes, Nitriles, and Ti Imidos
 via Oxidatively Induced N-N Bond Coupling.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b13173
_journal_year                    2020
_chemical_formula_moiety         'C25 H27 Cl2 N3 Ti'
_chemical_formula_sum            'C25 H27 Cl2 N3 Ti'
_chemical_formula_weight         488.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 106.174(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.1050(10)
_cell_length_b                   9.7060(5)
_cell_length_c                   15.0812(8)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.125
_cell_measurement_theta_min      2.435
_cell_volume                     2404.7(2)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'APEX3, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'Shelxle-(Rev. 825) (Huebschle, C. B. 2011)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            40761
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.177
_diffrn_reflns_theta_min         2.437
_diffrn_source                   'Bruker Photon-II CMOS'
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         9169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+1.4075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1118
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6446
_reflns_number_total             9169
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            18182_a.cif
_cod_data_source_block           18182_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4134214
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.6770
_shelx_estimated_absorpt_t_max   0.7465
_shelx_res_checksum              11987
_shelx_hkl_checksum              75990