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_4022343
_publ_contact_author
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     Prof. Gianluca Calestani
     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
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_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
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_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            'C21 H12 Cl N S'
_chemical_formula_weight         345.85
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             04/09/2002
_audit_creation_method           'ModiCIF v1.02'
_cell_angle_alpha                90.00(0)
_cell_angle_beta                 114.51(5)
_cell_angle_gamma                90.00(0)
_cell_formula_units_Z            4.00
_cell_length_a                   10.708(3)
_cell_length_b                   17.020(4)
_cell_length_c                   9.897(2)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    22
_cell_measurement_theta_max      32.5
_cell_measurement_theta_min      20.8
_cell_volume                     1641.2(10)
_computing_cell_refinement       'Belletti et al., 1993'
_computing_data_collection       'Belletti, Cantoni & Pasquinelli,1993'
_computing_data_reduction        'DIFAU (Belletti et al.)'
_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       'Siemens AED'
_diffrn_measurement_method       theta/2theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         fine-focussealedtube
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3262
_diffrn_reflns_theta_max         70.11
_diffrn_reflns_theta_min         4.54
_diffrn_standards_decay_%        .20
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.2364
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  .98
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.3997
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       needle
_exptl_crystal_F_000             712.0
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.722
_refine_ls_goodness_of_fit_obs   0.990
_refine_ls_hydrogen_treatment    not_refined
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.114
_refine_ls_restrained_S_obs      0.990
_refine_ls_R_factor_all          0.2171
_refine_ls_R_factor_obs          0.0415
_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^)+(0.0238P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2738
_refine_ls_wR_factor_obs         0.0672
_reflns_number_observed          947
_reflns_number_total             3104
_reflns_threshold_expression     '>2 sigma(I)'
_cod_data_source_file            jo0267504si20021122_042738_3.cif
_cod_data_source_block           dnredcl2
_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^)+(0.0238P)^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^)+(0.0238P)^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_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C21 H12 N1 S1 Cl1'
_cod_database_code               4022343