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_4516974
_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.
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_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_sum            'C24 H22 N6 O'
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_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
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_cell_angle_alpha                90
_cell_angle_beta                 92.320(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.0794(10)
_cell_length_b                   4.5338(2)
_cell_length_c                   19.1155(7)
_cell_measurement_reflns_used    3461
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      65.8188
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_cell_volume                     2085.15(15)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
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_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30499
_diffrn_reflns_point_group_measured_fraction_full 0.989
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_diffrn_reflns_theta_full        66.333
_diffrn_reflns_theta_max         66.333
_diffrn_reflns_theta_min         4.630
_diffrn_source_type              'Incoatec Cu-ImS'
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       Block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3639
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0785P)^2^+0.3018P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1461
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2377
_reflns_number_total             3639
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao9b01650_si_003.cif
_cod_data_source_block           solve01
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4516974
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.877
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              46660
_shelx_hkl_checksum              77341