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_1501962
_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         'C22 H21 N1 O2'
_chemical_formula_sum            'C22 H21 N O2'
_chemical_formula_weight         331.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 73.7676(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6999(3)
_cell_length_b                   13.5546(5)
_cell_length_c                   13.8504(6)
_cell_measurement_reflns_used    6880
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1748.43(11)
_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 0.993
_diffrn_measured_fraction_theta_max 0.992
_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  0.072
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13742
_diffrn_reflns_theta_full        26.903
_diffrn_reflns_theta_max         27.452
_diffrn_reflns_theta_min         5.179
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.37
_refine_ls_extinction_coef       170(50)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9462
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.000174
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 1.03P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1232
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1230
_reflns_limit_h_max              12
_reflns_limit_h_min              -11
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2295
_reflns_number_total             3967
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.18
_oxford_diffrn_Wilson_scale      7.96
_oxford_refine_ls_r_factor_ref   0.0869
_oxford_refine_ls_scale          0.3681(7)
_oxford_reflns_number_all        3350
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            ol103088r_si_002.cif
_cod_data_source_block           43
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C22 H21 N1 O2'
_cod_database_code               1501962