Three-Component Synthesis of Perfluoroalkyl- or Perfluoroaryl-Substituted 4-Hydroxypyridine Derivatives and Their Palladium-Catalyzed Coupling Reactions
Tilman Lechel; Jyotirmayee Dash; Paul Hommes; Dieter Lentz; Hans-Ulrich Reissig; Journal of Organic Chemistry 75 (2010) 726–732; doi:10.1021/jo9022183

data_4025192
_publ_contact_author
;
     Prof. Dr. Hans-Ulrich Reissig
     Institut f\"ur Chemie / Organische Chemie
     Freie Universit\"at Berlin
     Takustr. 3
     14195 Berlin
     Bundesrepublik Deutschland
;
_publ_contact_author_email       hans.reissig@chemie.fu-berlin.de
_publ_contact_author_fax         '049 30 83855367'
_publ_contact_author_phone       '049 30 83855330'
_publ_section_title
;
 Three-Component Synthesis of Perfluoroalkyl- or Perfluoroaryl-Substituted
 4-Hydroxypyridine Derivatives and Their Palladium-Catalyzed Coupling
 Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              726
_journal_page_last               732
_journal_paper_doi               10.1021/jo9022183
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C28 H24 F3 N'
_chemical_formula_weight         431.48
_chemical_melting_point          432.0(10)
_chemical_name_systematic
; 
 2-tert-Butyl-3,4,5-triphenyl-6-(trifluoromethyl)pyridine 
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   17.002(3)
_cell_length_b                   17.002(3)
_cell_length_c                   31.216(11)
_cell_measurement_reflns_used    975
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30.4
_cell_measurement_theta_min      2.7
_cell_volume                     9024(4)
_computing_cell_refinement       'SAINT (Bruker-AXS)'
_computing_data_collection       'SMART (BRuKER-AXS)'
_computing_data_reduction        'SAINT (Bruker-AXS)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-AXS SMART CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0686
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            32709
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3616
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0840P)^2^+22.5816P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1788
_refine_ls_wR_factor_ref         0.2104
_reflns_number_gt                3337
_reflns_number_total             4604
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9022183_si_002.cif
_cod_data_source_block           tl608
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '431-433 K' was changed to
'432.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multiscan' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

2020-08-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_original_formula_sum        'C12.44 H10.67 F1.33 N0.44'
_cod_original_formula_units_Z    36
_cod_original_formula_weight     191.77
_cod_database_code               4025192