Regioselective Ring Expansion of 2,4-Diiminoazetidines via Cleavage of C-N and C(sp3)-H Bonds: Efficient Construction of 2,3-Dihydropyrimidinesulfonamides
Yang Wang; Yue Chi; Wen-Xiong Zhang; Zhenfeng Xi; Journal of the American Chemical Society 134 (2012) 2926–2929; doi:10.1021/ja211486f

data_4117480
_publ_section_title
;
 Regioselective Ring Expansion of 2,4-Diiminoazetidines via Cleavage of
 C-N and C(sp3)-H Bonds: Efficient Construction of
 2,3-Dihydropyrimidinesulfonamides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2926
_journal_page_last               2929
_journal_paper_doi               10.1021/ja211486f
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C29 H37 N3 O2 S'
_chemical_formula_sum            'C29 H37 N3 O2 S'
_chemical_formula_weight         491.68
_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                 92.971(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3036(12)
_cell_length_b                   28.939(6)
_cell_length_c                   14.110(3)
_cell_measurement_reflns_used    7470
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.41
_cell_volume                     2570.5(9)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15526
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.9632
_exptl_absorpt_correction_T_min  0.9325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       rod
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0653
_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^)+(0.0400P)^2^+2.1570P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1415
_reflns_number_gt                5152
_reflns_number_total             5777
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja211486f_si_004.cif
_cod_data_source_block           8
_cod_database_code               4117480