Heteroaromatic synthesis via olefin cross-metathesis: entry to polysubstituted pyridines.
Donohoe, Timothy J.; Basutto, José A; Bower, John F.; Rathi, Akshat; Organic letters 13 (2011) 1036–1039; doi:10.1021/ol103088r

data_1501961
_publ_section_title
;
 Heteroaromatic synthesis via olefin cross-metathesis: entry to
 polysubstituted pyridines.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1036
_journal_page_last               1039
_journal_paper_doi               10.1021/ol103088r
_journal_volume                  13
_journal_year                    2011
_chemical_compound_source        Synthetic
_chemical_formula_moiety         'C20 H19 N1'
_chemical_formula_sum            'C20 H19 N'
_chemical_formula_weight         273.38
_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   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                68.3797(10)
_cell_angle_beta                 81.4469(9)
_cell_angle_gamma                62.3658(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3961(2)
_cell_length_b                   9.4690(2)
_cell_length_c                   10.2833(2)
_cell_measurement_reflns_used    2959
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     753.26(3)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10759
_diffrn_reflns_theta_full        25.492
_diffrn_reflns_theta_max         27.411
_diffrn_reflns_theta_min         5.172
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.80
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.28
_refine_ls_extinction_coef       190(40)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2765
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.000187
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.30P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1077
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1077
_reflns_limit_h_max              12
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -11
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2108
_reflns_number_total             3377
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.41
_oxford_diffrn_Wilson_scale      0.55
_oxford_refine_ls_r_factor_ref   0.0610
_oxford_refine_ls_scale          1.416(11)
_oxford_reflns_number_all        2765
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            ol103088r_si_001.cif
_cod_data_source_block           42
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_formula_sum        'C20 H19 N1'
_cod_database_code               1501961