New aspects of catalytic intramolecular C-H amination: unexpected formation of a seven-membered ring in nitrogen-containing systems.
Toumieux, Sylvestre; Compain, Philippe; Martin, Olivier R.; Selkti, Mohamed; Organic letters 8 (2006) 4493–4496; doi:10.1021/ol061649x

data_1506174
_publ_section_title
;
 New aspects of catalytic intramolecular C-H amination: unexpected
 formation of a seven-membered ring in nitrogen-containing systems.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4493
_journal_page_last               4496
_journal_paper_doi               10.1021/ol061649x
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C13 H18 N2 O5 S2'
_chemical_formula_sum            'C13 H18 N2 O5 S2'
_chemical_formula_weight         346.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 96.7179(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.5689(3)
_cell_length_b                   11.3899(2)
_cell_length_c                   17.4891(4)
_cell_measurement_temperature    293(2)
_cell_volume                     3080.02(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'KappaCCD (Nonius, 1998)'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12450
_diffrn_reflns_theta_full        26.67
_diffrn_reflns_theta_max         26.67
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         6468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0929P)^2^+1.7481P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1474
_reflns_number_gt                5048
_reflns_number_total             6468
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061649xsi20060705_091840.cif
_cod_data_source_block           compose4
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1506174