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_4117479
_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_sum            'C28 H34 Cl N3 O2 S'
_chemical_formula_weight         512.09
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 112.44(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.426(2)
_cell_length_b                   19.715(4)
_cell_length_c                   12.377(3)
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.06
_cell_volume                     2577.0(11)
_computing_cell_refinement       Rapid-AUTO
_computing_data_collection       'Rapid-AUTO (Rigaku,2000)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC,2000)'
_computing_molecular_graphics    'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material  SHELXL-97,(Sheldrick,1997)
_computing_structure_refinement  SHELXL-97,(Sheldrick,1997)
_computing_structure_solution    SHELXS-97,(Sheldrick,1997)
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       \W
_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  0.0598
_diffrn_reflns_av_sigmaI/netI    0.2062
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11354
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_correction_T_min  0.9498
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
                                  HIGASHI, T. (1995). Abscor-empirical 
                                  Absorption Correction based on Fourier 
                                  Series Approximation. 
                                  Rigaku Corporation,Tokyo,Japan. 
;
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         5901
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0190P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.1178
_reflns_number_gt                2520
_reflns_number_total             5901
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja211486f_si_003.cif
_cod_data_source_block           2a
_cod_original_cell_volume        2577.0(9)
_cod_database_code               4117479