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_4134212
_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         'C33 H30 Cl2 N2 Ti 0.5(C4 H10 O)'
_chemical_formula_sum            'C35 H35 Cl2 N2 O0.5 Ti'
_chemical_formula_weight         610.45
_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
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 97.5050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.9721(6)
_cell_length_b                   20.5620(6)
_cell_length_c                   15.0039(4)
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      28.7495
_cell_measurement_theta_min      2.5475
_cell_volume                     6108.8(3)
_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      125(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            72615
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.546
_diffrn_reflns_theta_min         2.232
_diffrn_source                   'Bruker Photon-III CMOS'
_exptl_absorpt_coefficient_mu    0.484
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       needle
_exptl_crystal_F_000             2552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.945
_refine_diff_density_min         -0.898
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     736
_refine_ls_number_reflns         18609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0636
_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^)+(0.0524P)^2^+6.8295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1516
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12312
_reflns_number_total             18609
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            19152_a.cif
_cod_data_source_block           19152_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

2020-03-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C70 H70 Cl4 N4 O Ti2'
_cod_original_formula_weight         1220.90
_cod_original_formula_moiety         '2(C33 H30 Cl2 N2 Ti) (C4 H10 O)'
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4134212
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              79325
_shelx_hkl_checksum              74833