Diastereoselective Synthesis of Cyclopentene Spiro-rhodanines Containing Three Contiguous Stereocenters via Phosphine-catalyzed [3+2] Cycloaddition or One-pot Sequential [3+2]/[3+2] Cycloaddition
Zhang, Jiayong; Zhang, Minxuan; Li, Yuming; Liu, Shuang; Miao, Zhiwei; RSC Adv.  (2016) –; doi:10.1039/C6RA23399F

data_7227028
_publ_section_title
;
 Diastereoselective Synthesis of Cyclopentene Spiro-rhodanines Containing
 Three Contiguous Stereocenters via Phosphine-catalyzed [3+2]
 Cycloaddition or One-pot Sequential [3+2]/[3+2] Cycloaddition
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA23399F
_journal_year                    2016
_chemical_compound_source        'mushroom amanita muscaria'
_chemical_formula_moiety         C28H31NO3S2Na1+
_chemical_formula_sum            'C28 H31 N O3 S2'
_chemical_formula_weight         493.66
_chemical_melting_point          283
_chemical_name_common            spirocompound
_chemical_name_systematic
'Ethyl 9-benzyl-3-(tert-butyl)-4-oxo-2-thioxo-6-(m-tolyl)-1-thia-3-azaspiro[4.4]non-7-ene-7-car- Boxylate'
_chemical_properties_physical    ', Hygroscopic'
_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
_audit_update_record
;
2016-10-21 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                76.88(3)
_cell_angle_beta                 77.78(3)
_cell_angle_gamma                72.35(3)
_cell_formula_units_Z            2
_cell_length_a                   10.588(2)
_cell_length_b                   10.777(2)
_cell_length_c                   12.326(3)
_cell_measurement_reflns_used    4050
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8904
_cell_measurement_theta_min      2.0429
_cell_volume                     1289.7(5)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0568
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13062
_diffrn_reflns_theta_full        27.92
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.9722
_exptl_absorpt_correction_T_min  0.9543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             524
_exptl_crystal_preparation       ', Luminescent'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ether'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         6028
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0677P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1132
_reflns_number_gt                4314
_reflns_number_total             6028
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra23399f2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7227028