Ambient-Light-Promoted Three-Component Annulation: Synthesis of Perfluoroalkylated Pyrimidines.
Wang, Rui; Guan, Wei; Han, Zheng-Bo; Liang, Fushun; Suga, Takeo; Bi, Xihe; Nishide, Hiroyuki; Organic letters 19 (2017) 2358–2361; doi:10.1021/acs.orglett.7b00894

data_1556043
_publ_section_title
;
 Ambient-Light-Promoted Three-Component Annulation: Synthesis of
 Perfluoroalkylated Pyrimidines.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2358
_journal_page_last               2361
_journal_paper_doi               10.1021/acs.orglett.7b00894
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C11 H10 F7 N3 O2'
_chemical_formula_weight         349.22
_chemical_melting_point          '63-64 &#x00A1;&#x00E6;'
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.161(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1302(11)
_cell_length_b                   7.5328(5)
_cell_length_c                   12.1195(13)
_cell_measurement_reflns_used    1945
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.1414
_cell_measurement_theta_min      3.0317
_cell_volume                     1472.6(2)
_computing_cell_refinement
'CrysAlisPro(1.171.35.21) (Agilent Tech., 2012)'
_computing_data_collection
'CrysAlisPro(1.171.35.21) (Agilent Tech., 2012)'
_computing_data_reduction
'CrysAlisPro(1.171.35.21) (Agilent Tech., 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10254
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.206
_diffrn_reflns_theta_min         3.362
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             775
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1327
_refine_ls_R_factor_gt           0.0745
_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^)+(0.1443P)^2^+0.0456P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2102
_refine_ls_wR_factor_ref         0.2647
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1815
_reflns_number_total             3576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00894_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1556043
_shelxl_version_number           2013-4
_shelx_res_checksum              34208
_shelx_hkl_checksum              44573