An unprecedented approach to 4,5-disubstituted pyrimidine derivatives by a ZnCl(2)-catalyzed three-component coupling reaction.
Sasada, Toshiaki; Kobayashi, Fuminori; Sakai, Norio; Konakahara, Takeo; Organic letters 11 (2009) 2161–2164; doi:10.1021/ol900382j

data_1503859
_publ_section_title
;
 An unprecedented approach to 4,5-disubstituted pyrimidine derivatives by
 a ZnCl(2)-catalyzed three-component coupling reaction.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2161
_journal_page_last               2164
_journal_paper_doi               10.1021/ol900382j
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C18 H14 N2 O'
_chemical_formula_weight         274.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.533(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.380(4)
_cell_length_b                   7.301(3)
_cell_length_c                   15.108(5)
_cell_measurement_reflns_used    1148
_cell_measurement_temperature    299
_cell_measurement_theta_max      25.47
_cell_measurement_theta_min      2.30
_cell_volume                     1350.4(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      299
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0789
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7657
_diffrn_reflns_theta_full        27.84
_diffrn_reflns_theta_max         27.84
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9692
_exptl_absorpt_correction_T_min  0.9676
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.740
_refine_ls_hydrogen_treatment    calc
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.740
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1742P)^2^+2.4975P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1810
_refine_ls_wR_factor_ref         0.2239
_reflns_number_gt                1974
_reflns_number_total             3037
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900382j_si_003.cif
_cod_data_source_block           13a
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1503859