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_7156725
_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            'C18 H15 N O3 S'
_chemical_formula_weight         325.37
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 107.498(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1858(4)
_cell_length_b                   8.0088(2)
_cell_length_c                   15.5088(4)
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_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4460
_cell_measurement_theta_min      3.1000
_cell_volume                     1561.98(8)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
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_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_molecular_graphics    Ortep3
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_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 0.999
_diffrn_measured_fraction_theta_max 0.904
_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  0.0557
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_k_max       10
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_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.904
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_diffrn_reflns_theta_max         28.935
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_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            COLURLESS
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
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_refine_ls_number_reflns         3730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0588P)^2^+0.7010P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1623
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2411
_reflns_number_total             3730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00433e2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7156724--7156726.cif.'
_cod_database_code               7156725
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.972
_oxdiff_exptl_absorpt_empirical_full_min 0.799
_oxdiff_exptl_absorpt_empirical_full_max 1.198
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              7585