Metal-Free Oxidative Spirocyclization of Alkynes with Sulfonylhydrazides Leading to 3-Sulfonated Azaspiro[4,5]trienones.
Wen, Jiangwei; Wei, Wei; Xue, Shengnan; Yang, Daoshan; Lou, Yu; Gao, Chaoyang; Wang, Hua; The Journal of organic chemistry 80 (2015) 4966–4972; doi:10.1021/acs.joc.5b00361

data_4031070
_publ_section_title
;
 Metal-Free Oxidative Spirocyclization of Alkynes with Sulfonylhydrazides
 Leading to 3-Sulfonated Azaspiro[4,5]trienones.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4966
_journal_page_last               4972
_journal_paper_doi               10.1021/acs.joc.5b00361
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C22 H17 N O4 S,C H Cl3'
_chemical_formula_sum            'C23 H18 Cl3 N O4 S'
_chemical_formula_weight         510.79
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.494(3)
_cell_length_b                   12.538(3)
_cell_length_c                   16.684(4)
_cell_measurement_reflns_used    3318
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20.59
_cell_measurement_theta_min      2.06
_cell_volume                     2404.4(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex CCD'
_diffrn_measurement_method       '\f amd \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  0.0675
_diffrn_reflns_av_sigmaI/netI    0.0608
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18455
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.498
_exptl_absorpt_correction_T_max  0.9427
_exptl_absorpt_correction_T_min  0.8412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0579
_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^)+(0.0671P)^2^+0.5253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                3473
_reflns_number_total             4696
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00361_si_002.cif
_cod_data_source_block           sad
_cod_original_cell_volume        2404.5(10)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               4031070