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_4025191
_publ_contact_author
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     Prof. Dr. Hans-Ulrich Reissig
     Institut f\"ur Chemie / Organische Chemie
     Freie Universit\"at Berlin
     Takustr. 3
     14195 Berlin
     Bundesrepublik Deutschland
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_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
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 Three-Component Synthesis of Perfluoroalkyl- or Perfluoroaryl-Substituted
 4-Hydroxypyridine Derivatives and Their Palladium-Catalyzed Coupling
 Reactions
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_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            'C16 H16 N2 O'
_chemical_formula_weight         252.31
_chemical_melting_point          435.5(5)
_chemical_name_systematic
; 
 5-(Benzyloxy)-2,4,6-trimethylnicotinnitrile 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 93.391(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.368(2)
_cell_length_b                   10.165(2)
_cell_length_c                   14.648(3)
_cell_measurement_reflns_used    775
_cell_measurement_temperature    173
_cell_measurement_theta_max      30.43
_cell_measurement_theta_min      2.5
_cell_volume                     1392.4(5)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans with .3 deg in omega'
_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  0.0604
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9743
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          .48
_exptl_crystal_size_mid          .19
_exptl_crystal_size_min          .08
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0764P)^2^+0.2004P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1605
_reflns_number_gt                2162
_reflns_number_total             3465
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9022183_si_001.cif
_cod_data_source_block           orglechm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_cell_measurement_temperature' value '173k' was changed to '173' -
the value should be numeric and without a unit
designator.

'_chemical_melting_point' value '435-436 K' was changed
to '435.5(5)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
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_cod_database_code               4025191