Copper-Catalyzed Cascade Preparation of Dihydropyrimidin-4-ones from N-(Prop-2-yn-1-yl)amides and Azides
Jinjin Wang; Jing Wang; Ping Lu; Yanguang Wang; Journal of Organic Chemistry 78 (2013) 8816–8820; doi:10.1021/jo401094j

data_4028525
_publ_section_title
;
 Copper-Catalyzed Cascade Preparation of Dihydropyrimidin-4-ones from
 N-(Prop-2-yn-1-yl)amides and Azides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8816
_journal_page_last               8820
_journal_paper_doi               10.1021/jo401094j
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C18 H18 N2 O4 S'
_chemical_formula_sum            'C18 H18 N2 O4 S'
_chemical_formula_weight         358.40
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.304(7)
_cell_angle_beta                 97.336(6)
_cell_angle_gamma                90.168(6)
_cell_formula_units_Z            2
_cell_length_a                   7.5283(6)
_cell_length_b                   10.4136(8)
_cell_length_c                   12.1829(9)
_cell_measurement_reflns_used    2222
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5623
_cell_measurement_theta_min      3.0716
_cell_volume                     861.70(13)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w 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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5922
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.9349
_exptl_absorpt_correction_T_min  0.9101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.146(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0348P)^2^+0.1930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                2564
_reflns_number_total             3148
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401094j_si_002.cif
_cod_data_source_block           110929_wjj570144_2
_cod_original_cell_volume        861.70(11)
_cod_database_code               4028525