Sustainable Synthetic Approach for (Pyrazol-4-ylidene)pyridines By Metal Catalyst-Free Aerobic C(sp<sup>2</sup>)-C(sp<sup>3</sup>) Coupling Reactions between 1-Amino-2-imino-pyridines and 1-Aryl-5-pyrazolones.
Ibrahim, Hamada Mohamed; Behbehani, Haider; ACS omega 4 (2019) 11701–11711; doi:10.1021/acsomega.9b01650

data_4516975
_publ_section_title
;
 Sustainable Synthetic Approach for (Pyrazol-4-ylidene)pyridines By Metal
 Catalyst-Free Aerobic C(sp<sup>2</sup>)-C(sp<sup>3</sup>) Coupling
 Reactions between 1-Amino-2-imino-pyridines and 1-Aryl-5-pyrazolones.
;
_journal_issue                   7
_journal_name_full               'ACS omega'
_journal_page_first              11701
_journal_page_last               11711
_journal_paper_doi               10.1021/acsomega.9b01650
_journal_volume                  4
_journal_year                    2019
_chemical_formula_moiety         'C22 H17 Br N6 O, 0.5(H2 O)'
_chemical_formula_sum            'C22 H18 Br N6 O1.5'
_chemical_formula_weight         470.32
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      13
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.057(9)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   17.612(13)
_cell_length_b                   7.593(6)
_cell_length_c                   15.880(12)
_cell_measurement_reflns_used    937
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.95
_cell_measurement_theta_min      3.00
_cell_volume                     2007(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1102
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11054
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.085
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             956.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.770
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3482
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0694
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0985P)^2^+0.2084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2197
_reflns_number_gt                1614
_reflns_number_total             3482
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ao9b01650_si_002.cif
_cod_data_source_block           User-defined
_cod_depositor_comments
;

2021-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     'C44 H36 Br2 N12 O3'
_cod_original_formula_sum        'C44 H36 Br2 N12 O3'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     940.65
_cod_database_code               4516975