Synthesis of 1<i>H</i>-Pyrazol-5-yl-pyridin-2-yl-[1,2,4]triazinyl Soft-Lewis Basic Complexants via Metal and Oxidant Free [3 + 2] Dipolar Cycloaddition of Terminal Ethynyl Pyridines with Tosylhydrazides.
Veerakanellore, Giri Babu; Smith, Caris M.; Vasiliu, Monica; Oliver, Allen G.; Dixon, David A.; Carrick, Jesse D.; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02088

data_4033625
_publ_section_title
;
 Synthesis of 1<i>H</i>-Pyrazol-5-yl-pyridin-2-yl-[1,2,4]triazinyl
 Soft-Lewis Basic Complexants via Metal and Oxidant Free [3 + 2] Dipolar
 Cycloaddition of Terminal Ethynyl Pyridines with Tosylhydrazides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02088
_journal_year                    2019
_chemical_formula_moiety         'C30 H22 N6, C4 H8 O, C2 H6 O'
_chemical_formula_sum            'C36 H36 N6 O2'
_chemical_formula_weight         584.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 114.053(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0293(11)
_cell_length_b                   30.286(3)
_cell_length_c                   11.1297(11)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.41
_cell_volume                     3394.9(6)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            68338
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.320
_diffrn_reflns_theta_min         2.114
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9462
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_description       rod
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.675
_exptl_crystal_size_mid          0.406
_exptl_crystal_size_min          0.324
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         8442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0617P)^2^+1.6923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6964
_reflns_number_total             8442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02088_si_002.cif
_cod_data_source_block           vgbb279
_cod_database_code               4033625
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.977
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_shelx_res_checksum              26401
_shelx_hkl_checksum              58411
_shelx_fab_checksum              75948