Catalyst-Controlled Amino- versus Oxy-Acetoxylation of Urea-Tethered Alkenes: Efficient Synthesis of Cyclic Ureas and Isoureas.
Rao, Wei-Hao; Yin, Xue-Song; Shi, Bing-Feng; Organic letters 17 (2015) 3758–3761; doi:10.1021/acs.orglett.5b01741

data_1529858
_publ_section_title
;
 Catalyst-Controlled Amino- versus Oxy-Acetoxylation of Urea-Tethered
 Alkenes: Efficient Synthesis of Cyclic Ureas and Isoureas.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3758
_journal_page_last               3761
_journal_paper_doi               10.1021/acs.orglett.5b01741
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C20 H22 N2 O5 S'
_chemical_formula_sum            'C20 H22 N2 O5 S'
_chemical_formula_weight         402.46
_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                90.789(2)
_cell_angle_beta                 92.849(2)
_cell_angle_gamma                107.436(6)
_cell_formula_units_Z            2
_cell_length_a                   5.9849(3)
_cell_length_b                   8.3500(4)
_cell_length_c                   21.2894(10)
_cell_measurement_reflns_used    5659
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     1013.32(9)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8898
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.044(4)
_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   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.8358P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1808
_reflns_number_gt                2338
_reflns_number_total             3993
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01741_si_002.cif
_cod_data_source_block           r79613
_cod_original_cell_volume        1013.32(8)
_cod_database_code               1529858