De Novo Ring-Forming Consecutive Four-Component Syntheses of 4-Pyrazolyl-1,2,3-triazoles from (Triisopropylsilyl)butadiyne as a C4 Building Block.
Niesobski, Patrik; Klukas, Fabian; Berens, Henning; Makhloufi, Gamall; Janiak, Christoph; Müller, Thomas J J; The Journal of organic chemistry 83 (2018) 4851–4858; doi:10.1021/acs.joc.8b00430

data_4034951
_publ_section_title
;
 De Novo Ring-Forming Consecutive Four-Component Syntheses of
 4-Pyrazolyl-1,2,3-triazoles from (Triisopropylsilyl)butadiyne as a C4
 Building Block.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4851
_journal_page_last               4858
_journal_paper_doi               10.1021/acs.joc.8b00430
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C19 H17 N5'
_chemical_formula_sum            'C19 H17 N5'
_chemical_formula_weight         315.38
_chemical_name_systematic
;
1-benzyl-4-(1-methyl-3-phenyl-1H-pyrazol-5-yl)-1H-1,2,3-triazole
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.379(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.377(2)
_cell_length_b                   16.459(4)
_cell_length_c                   10.573(3)
_cell_measurement_reflns_used    1322
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.036
_cell_measurement_theta_min      2.250
_cell_volume                     1573.4(7)
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2015)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       '\w scans, \f scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13256
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.680
_diffrn_reflns_theta_max         24.679
_diffrn_reflns_theta_min         2.253
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Sheldrick, 2012)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0121(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2008)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+0.3231P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1844
_reflns_number_total             2648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00430_si_002.cif
_cod_data_source_block           HB33
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034951
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              92255
_shelx_hkl_checksum              23348