Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles.
Mohamady, Samy; Kralt, Braden; Samwel, Shery K.; Taylor, Scott D.; ACS omega 3 (2018) 15566–15574; doi:10.1021/acsomega.8b02304

data_4516122
_publ_section_title
;
 Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted
 Pyrazoles.
;
_journal_issue                   11
_journal_name_full               'ACS omega'
_journal_page_first              15566
_journal_page_last               15574
_journal_paper_doi               10.1021/acsomega.8b02304
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C15 H12 N2'
_chemical_formula_sum            'C15 H12 N2'
_chemical_formula_weight         220.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016
_cell_angle_alpha                90
_cell_angle_beta                 109.597(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   16.9414(6)
_cell_length_b                   17.1524(6)
_cell_length_c                   17.6605(5)
_cell_measurement_reflns_used    923
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      1.5
_cell_volume                     4834.6(3)
_computing_cell_refinement       'SMART, 'Bruker APEX II'
_computing_data_collection       'Bruker Kappa APEX II'
_computing_data_reduction        'SAINT, 'Bruker APEX II'
_computing_molecular_graphics    Mercury
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2016)'
_diffrn_ambient_temperature      296(2)
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_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'BRUKER SMART APEX II'
_diffrn_measurement_method       'Omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0818
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
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_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
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_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.363
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  3
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.00043(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4749
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1472
_refine_ls_R_factor_gt           0.0524
_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^)+(0.0248P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0910
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2148
_reflns_number_total             4749
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b02304_si_001.cif
_cod_data_source_block           twin4
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4516122
_shelx_estimated_absorpt_t_min   0.988
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              21004
_shelx_hkl_checksum              45368