An effective and general method for the highly regioselective synthesis of 1-phenylpyrazoles from β-enaminoketoesters, tandem Blaise–acylation adducts
Ko, Young Ok; Chun, Yu Sung; Park, Cho-Long; Kim, Youngmee; Shin, Hyunik; Ahn, Sungho; Hong, Jongki; Lee, Sang-gi; Organic & Biomolecular Chemistry 7 (2009) 1132–1136; doi:10.1039/b820324e

data_7150590
_publ_section_title
;
 An effective and general method for the highly regioselective
 synthesis of 1-phenylpyrazoles from \b-enaminoketoesters, tandem
 Blaise--acylation adducts
;
_journal_issue                   6
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1132
_journal_page_last               1136
_journal_paper_doi               10.1039/b820324e
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C25 H19 F3 N2 O2'
_chemical_formula_weight         436.42
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                78.875(5)
_cell_angle_beta                 88.801(5)
_cell_angle_gamma                64.005(4)
_cell_formula_units_Z            2
_cell_length_a                   9.801(2)
_cell_length_b                   9.982(2)
_cell_length_c                   12.377(3)
_cell_measurement_reflns_used    470
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      20.15
_cell_measurement_theta_min      2.32
_cell_volume                     1065.1(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1207
_diffrn_reflns_av_sigmaI/netI    0.3516
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5963
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.0067(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.714
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.714
_refine_ls_R_factor_all          0.2089
_refine_ls_R_factor_gt           0.0684
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1613
_reflns_number_gt                2041
_reflns_number_total             4052
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b820324e.txt
_cod_data_source_block           2f
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1065.2(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150590