Carbodiimide insertion into sulfonimides: one-step route to azepine derivatives via a two-atom saccharin ring expansion.
Tan, Davin; Friščić, Tomislav; Chemical communications (Cambridge, England) 53 (2017) 901–904; doi:10.1039/c6cc07331j

data_7119211
_publ_section_title
;
 Carbodiimide insertion into sulfonimides: one-step route to azepine
 derivatives via a two-atom saccharin ring expansion.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              901
_journal_page_last               904
_journal_paper_doi               10.1039/c6cc07331j
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C28 H37 N3 O3 S'
_chemical_formula_weight         495.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-07-16 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.9780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.0370(3)
_cell_length_b                   35.2714(10)
_cell_length_c                   12.5698(3)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.23
_cell_measurement_theta_min      2.51
_cell_volume                     5297.1(2)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1279
_diffrn_reflns_av_unetI/netI     0.1046
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            89740
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.591
_diffrn_reflns_theta_min         3.542
_exptl_absorpt_coefficient_mu    1.351
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       Needle
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.36(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1270
_refine_ls_number_reflns         20864
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0747P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1531
_reflns_Friedel_coverage         0.967
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                14988
_reflns_number_total             20864
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc07331j2.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 7119206--7119214.cif.'
_cod_database_code               7119211
_shelxl_version_number           2013-4
_shelx_res_checksum              83716