Oxidative Trimerization of Amino Acids: Selective Synthesis of 2,3,5-Trisubstituted Pyridines.
Xiang, Jia-Chen; Cheng, Yan; Wang, Zi-Xuan; Ma, Jin-Tian; Wang, Miao; Tang, Bo-Cheng; Wu, Yan-Dong; Wu, An-Xin; Organic letters 19 (2017) 2997–3000; doi:10.1021/acs.orglett.7b01232

data_1546232
_publ_section_title
;
 Oxidative Trimerization of Amino Acids: Selective Synthesis of
 2,3,5-Trisubstituted Pyridines.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2997
_journal_page_last               3000
_journal_paper_doi               10.1021/acs.orglett.7b01232
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C24 H14 F3 N O'
_chemical_formula_weight         389.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.635(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4652(12)
_cell_length_b                   10.8048(11)
_cell_length_c                   17.209(2)
_cell_measurement_reflns_used    1347
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.11
_cell_measurement_theta_min      2.46
_cell_volume                     1873.9(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11866
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.038
_diffrn_reflns_theta_max         25.038
_diffrn_reflns_theta_min         2.021
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       Block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0760P)^2^+0.0748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1571
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1909
_reflns_number_total             3308
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01232_si_003.cif
_cod_data_source_block           1_a
_cod_database_code               1546232
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              54552
_shelx_hkl_checksum              59683