Use of dissolving metals in the partial reduction of pyridines: formation of 2-alkyl-1,2-dihydropyridines
Donohoe, Timothy J.; McRiner, Andrew J.; Helliwell, Madeleine; Sheldrake, Peter; Journal of the Chemical Society, Perkin Transactions 1  (2001) 1435–; doi:10.1039/b101662h

data_7204112
_publ_section_title
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 Use of dissolving metals in the partial reduction of pyridines:
 formation of 2-alkyl-1,2-dihydropyridines&#x200A;
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_journal_issue                   12
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1435
_journal_paper_doi               10.1039/b101662h
_journal_year                    2001
_chemical_formula_sum            'C15 H23 N O4'
_chemical_formula_weight         281.34
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             19100-04-05
_audit_creation_method           'by teXsan v1.7'
_audit_update_record
;
?
;
_cell_angle_alpha                90.00
_cell_angle_beta                 116.14(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.365(11)
_cell_length_b                   11.860(5)
_cell_length_c                   12.158(6)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      16.7
_cell_measurement_theta_min      14.8
_cell_volume                     3283(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan (MSC, 1995)'
_computing_publication_material  'teXsan (MSC, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SHELXS86 (Sheldrick, 1985)
;
_diffrn_ambient_temperature      296.2
_diffrn_measured_fraction_theta_full 0.439
_diffrn_measured_fraction_theta_max 0.439
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2953
_diffrn_reflns_theta_full        70.10
_diffrn_reflns_theta_max         70.10
_diffrn_reflns_theta_min         3.88
_diffrn_standards_decay_%        -2.55
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_type
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0007(2)
_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   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0747
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1447P)^2^+2.4372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2223
_refine_ls_wR_factor_ref         0.2549
_reflns_number_gt                1898
_reflns_number_total             2886
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b101662h.txt
_cod_data_source_block           compound_11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1447P)^2^+2.4372P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1447P)^2^+2.4372P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3284(2)
_cod_original_sg_symbol_H-M      'C 2/c      '
_cod_database_code               7204112