Effect of Sulfonyl Protecting Groups on the Neighboring Group Participation Ability of Sulfonamido Nitrogen
Nicolas Proust; Judith C. Gallucci; Leo A. Paquette; Journal of Organic Chemistry 74 (2009) 2897–2900; doi:10.1021/jo900065q

data_4024446
_publ_section_title
;
Effect of Sulfonyl Protecting Groups on the Neighboring Group Participation
Ability of Sulfonamido Nitrogen
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2897
_journal_page_last               2900
_journal_paper_doi               10.1021/jo900065q
_journal_volume                  74
_journal_year                    2009
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         '3(C23 H21 Br2 N3 O7 S2), 1.85(C1 H2 Cl2)'
_chemical_formula_sum            'C70.85 H66.7 Br6 Cl3.7 N9 O21 S6'
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_chemical_name_systematic
;
 ?
;
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_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                62.524(3)
_cell_angle_beta                 81.547(3)
_cell_angle_gamma                86.098(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7822(16)
_cell_length_b                   24.463(5)
_cell_length_c                   24.531(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.7749
_cell_volume                     4098.4(15)
_computing_cell_refinement       'Bruker SAINT v7.56A'
_computing_data_collection       'Bruker APEX2 v2008.5.0'
_computing_data_reduction        'Bruker SAINT v7.56A'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
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_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7749
_diffrn_reflns_av_R_equivalents  0.084
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            44462
_diffrn_reflns_theta_full        29.09
_diffrn_reflns_theta_max         29.09
_diffrn_reflns_theta_min         4.04
_exptl_absorpt_coefficient_mu    4.056
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Sheldrick)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2183.5
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         5.122
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.0683
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0823P)^2^+5.8874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1594
_refine_ls_wR_factor_ref         0.1832
_reflns_number_gt                9994
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_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo900065q_si_002.cif
_cod_data_source_block           Paquette1707
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024446