Polyhalogenated heterocyclic compounds. Part 47. Syntheses of multi-substituted pyridine derivatives from pentafluoropyridine
Richard D. Chambers; Philip R. Hoskin; Graham Sandford; Dmitrii S. Yufit; Judith A. K. Howard; Journal of the Chemical Society, Perkin Transactions 1  (2001) 2788–2795; doi:10.1039/B105950P

data_7238064
_publ_section_title
;
 Polyhalogenated heterocyclic compounds. Part 47. Syntheses of
 multi-substituted pyridine derivatives from pentafluoropyridine
;
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2788
_journal_page_last               2795
_journal_paper_doi               10.1039/B105950P
_journal_year                    2001
_chemical_formula_sum            'C14 H13 Br F8 N2 O'
_chemical_formula_weight         457.17
_chemical_melting_point          82.0(10)
_chemical_name_systematic
; 
4-[1-(trifluoromethyl)-1,2,2,2-tetrafluoroethyl]-
2-bromo-3-fluoro-5-methoxy-6-piperidylpyridine 
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.86(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.530(2)
_cell_length_b                   13.802(3)
_cell_length_c                   11.485(2)
_cell_measurement_reflns_used    997
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      20.8
_cell_measurement_theta_min      10.2
_cell_volume                     1669.0(6)
_computing_cell_refinement       'Bruker SAINT'
_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      120(1)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  SMART
_diffrn_measurement_method       \w-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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17323
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.553
_exptl_absorpt_correction_T_max  0.5794
_exptl_absorpt_correction_T_min  0.3503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.24
_refine_diff_density_max         2.249
_refine_diff_density_min         -1.279
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       0.005(1)
_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   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0692
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+8.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.1802
_reflns_number_gt                3118
_reflns_number_total             3834
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b105950p.cif
_cod_data_source_block           187s
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '81.1-83.0' was changed to
'82.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1669.1(6)
_cod_original_sg_symbol_H-M      'P 2~1~/c'
_cod_database_code               7238064