Cascade Radical Reactions via α-(Arylsulfanyl)imidoyl Radicals: Competitive [4 + 2] and [4 + 1] Radical Annulations of Alkynyl Isothiocyanates with Aryl Radicals
Luisa Benati; Gianluca Calestani; Rino Leardini; Matteo Minozzi; Daniele Nanni; Piero Spagnolo; Samantha Strazzari; Giuseppe Zanardi; Journal of Organic Chemistry 68 (2003) 3454–3464; doi:10.1021/jo0267504

data_4022342
_publ_contact_author
;
     Prof. Calestani Gianluca
     Universit\',chr(39),'a di Parma')
     Dipartimento di Chimica Generale ed Inorganica
     Chimica Analitica, Chimica Fisica
     Viale delle Scienze 17/A
     I-43100 Parma
     Italy
;
_publ_contact_author_email       calestg@at@ipruniv.cce.unipr.it
_publ_contact_author_fax         '[039]521 905 556'
_publ_contact_author_phone       '[039]521 905 447'
_publ_section_title
;
 Cascade Radical Reactions via \a-(Arylsulfanyl)imidoyl Radicals:
 Competitive [4 + 2] and [4 + 1] Radical Annulations
 of Alkynyl Isothiocyanates with Aryl Radicals
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3454
_journal_page_last               3464
_journal_paper_doi               10.1021/jo0267504
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C22 H12 F3 N S'
_chemical_formula_weight         379.40
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             11/10/2002
_audit_creation_method           'ModiCIF v1.02'
_cell_angle_alpha                90.00(0)
_cell_angle_beta                 90.00(0)
_cell_angle_gamma                90.00(0)
_cell_formula_units_Z            4.00
_cell_length_a                   11.347(2)
_cell_length_b                   7.126(2)
_cell_length_c                   21.266(3)
_cell_measurement_reflns_used    63
_cell_measurement_temperature    22
_cell_volume                     1719.5(6)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_publication_material  'PARST (Nardelli, 1983)'
_computing_structure_refinement  'SHELXS-93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR97 (Altomare et al., 1998)'
_diffrn_ambient_temperature      22
_diffrn_measurement_device       'Bruker AXS 100 CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         fine-focussealedtube
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1039
_diffrn_reflns_av_sigmaI/netI    0.0956
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8636
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.2248
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.998
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            RED
_exptl_crystal_density_diffrn    1.4655
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       ' needle'
_exptl_crystal_F_000             776.0
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.855
_refine_ls_goodness_of_fit_obs   1.159
_refine_ls_hydrogen_treatment    not_refined
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1385
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.840
_refine_ls_restrained_S_obs      1.190
_refine_ls_R_factor_all          0.1545
_refine_ls_R_factor_obs          0.0517
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0630P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1421
_refine_ls_wR_factor_obs         0.1138
_reflns_number_observed          637
_reflns_number_total             1671
_reflns_threshold_expression     '>2 sigma(I)'
_cod_data_source_file            jo0267504si20021122_042738_2.cif
_cod_data_source_block           dnred1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0630P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0630P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_formula_sum        'C22 H12 N1 F3 S1'
_cod_database_code               4022342