Chemoselective cyclization of N-sulfonyl ketimines with ethenesulfonyl fluorides: access to trans-cyclopropanes and fused-dihydropyrroles.
Arupula, Sanjeeva Kumar; Gudimella, Santosh K.; Guin, Soumitra; Mobin, Shaikh M.; Samanta, Sampak; Organic & biomolecular chemistry 17 (2019) 3451–3461; doi:10.1039/c9ob00433e

data_7156726
_publ_section_title
;
 Chemoselective cyclization of N-sulfonyl ketimines with ethenesulfonyl
 fluorides: access to trans-cyclopropanes and fused-dihydropyrroles.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3451
_journal_page_last               3461
_journal_paper_doi               10.1039/c9ob00433e
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C24.75 H22.5 F2 N O4 S2'
_chemical_formula_weight         500.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-11-24 deposited with the CCDC.    2019-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.801(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2102(5)
_cell_length_b                   11.1069(3)
_cell_length_c                   15.6812(6)
_cell_measurement_reflns_used    7473
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2910
_cell_measurement_theta_min      3.7150
_cell_volume                     2202.60(14)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       \w/q-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17722
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.142
_diffrn_reflns_theta_min         3.276
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0734P)^2^+0.8312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1635
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3769
_reflns_number_total             5225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00433e2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7156724--7156726.cif.'
_cod_original_formula_sum        'C24.75 H22.50 F2 N O4 S2'
_cod_database_code               7156726
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.909
_shelx_estimated_absorpt_t_max   0.949
_oxdiff_exptl_absorpt_empirical_full_min 0.820
_oxdiff_exptl_absorpt_empirical_full_max 1.326
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              67692