Core Scaffold-Inspired Stereoselective Synthesis of Spiropyrazolones via an Organocatalytic Michael/Cyclization Sequence
Luping Liu; Yuan Zhong; Panpan Zhang; Xianxing Jiang; Rui Wang; Journal of Organic Chemistry 77 (2012) 10228–10234; doi:10.1021/jo301851a

data_4027726
_publ_section_title
;
 Core Scaffold-Inspired Stereoselective Synthesis of Spiropyrazolones via
 an Organocatalytic Michael/Cyclization Sequence
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10228
_journal_page_last               10234
_journal_paper_doi               10.1021/jo301851a
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C23 H20 N4 O4 S'
_chemical_formula_weight         448.49
_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                 106.582(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.07(2)
_cell_length_b                   11.657(17)
_cell_length_c                   15.58(2)
_cell_measurement_reflns_used    1045
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.62
_cell_measurement_theta_min      2.22
_cell_volume                     2449(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.1016
_diffrn_reflns_av_sigmaI/netI    0.1292
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12991
_diffrn_reflns_theta_full        24.92
_diffrn_reflns_theta_max         24.92
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.9691
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_platon_squeeze_details          ' '
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1826
_refine_ls_R_factor_gt           0.0891
_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^)+(0.0822P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1945
_refine_ls_wR_factor_ref         0.2244
_reflns_number_gt                1908
_reflns_number_total             4251
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301851a_si_002.cif
_cod_data_source_block           p21c
_cod_original_cell_volume        2448(6)
_cod_database_code               4027726