Trifluoromethyl-substituted pyridyl- and pyrazolylboronic acids and esters: synthesis and Suzuki–Miyaura cross-coupling reactions
Clapham, Kate M.; Batsanov, Andrei S.; Bryce, Martin R.; Tarbit, Brian; Organic & Biomolecular Chemistry 7 (2009) 2155–2161; doi:10.1039/b901024f

data_7200928
_publ_section_title
;
 Trifluoromethyl-substituted pyridyl- and pyrazolylboronic acids and
 esters: synthesis and Suzuki--Miyaura cross-coupling reactions
;
_journal_issue                   10
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              2155
_journal_page_last               2161
_journal_paper_doi               10.1039/b901024f
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C15 H10 F3 N5 O2'
_chemical_formula_sum            'C15 H10 F3 N5 O2'
_chemical_formula_weight         349.28
_chemical_melting_point          440.5(8)
_chemical_name_common
;5-(3-(trifluoromethyl)-1-phenyl-1H-pyrazol-5-yl)-3-
nitropyridin-2-amine
;
_chemical_name_systematic
; 5-{3-(trifluoromethyl)-1-phenyl-1H-pyrazol-5-yl}-
3-nitropyridin-2-amine
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                83.57(2)
_cell_angle_beta                 82.56(3)
_cell_angle_gamma                85.02(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8768(8)
_cell_length_b                   8.4512(12)
_cell_length_c                   15.156(2)
_cell_measurement_reflns_used    5170
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.06
_cell_measurement_theta_min      2.43
_cell_volume                     739.71(19)
_computing_cell_refinement       'SAINT version 7.46A (Bruker, 2007)'
_computing_data_collection       'SMART version 5.049 (Bruker, 1998)'
_computing_data_reduction        'SAINT version 7.46A (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL version 6.14 (Bruker, 2003)'
_computing_publication_material  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_refinement  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_solution    'SHELXTL version 6.14 (Bruker, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Siemens SMART 1K CCD area detector'
_diffrn_measurement_method       '\w 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  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8679
_diffrn_reflns_theta_full        29.06
_diffrn_reflns_theta_max         29.06
_diffrn_reflns_theta_min         1.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0471P)^2^+0.2192P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0940
_reflns_number_gt                3259
_reflns_number_total             3896
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b901024f.txt
_cod_data_source_block           36
_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        739.74(18)
_cod_database_code               7200928