Regiodivergent sulfonylation of terminal olefins via dearomative rearrangement
Blé-González, Ever A.; Isbel, Stephen R.; Ojo, Olatunji S.; Hillesheim, Patrick C.; Zeller, Matthias; Bugarin, Alejandro; New Journal of Chemistry 47 (2023) 17020–17025; doi:10.1039/D3NJ03595F

data_7062686
_publ_section_title
;
 Regiodivergent sulfonylation of terminal olefins via dearomative
 rearrangement
;
_journal_issue                   36
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17020
_journal_page_last               17025
_journal_paper_doi               10.1039/D3NJ03595F
_journal_volume                  47
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H16 O2 S'
_chemical_formula_weight         272.35
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-04-30 deposited with the CCDC.	2023-08-21 downloaded from the CCDC.
;
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_cell_angle_gamma                90
_cell_formula_units_Z            2
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_cell_length_b                   5.5115(2)
_cell_length_c                   12.1835(5)
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    150(2)
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_cell_measurement_theta_min      2.4613
_cell_volume                     692.64(5)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'Apex4 v2022.10-0 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_refinement
;  
SHELXL-2018/3 (Sheldrick, 2015a, 2018), 
SHELXLE Rev1460 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_detector_type
'PhotonII charge-integrating pixel array (CPAD)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22252
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.290
_diffrn_reflns_theta_min         2.718
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       rod
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Flack x determined using 1973 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         5306
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0644P)^2^+0.0750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1047
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                4738
_reflns_number_total             5306
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj03595f2.cif
_cod_data_source_block           AB_02_0m
_cod_depositor_comments
'Adding full bibliography for 7062686--7062687.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7062686
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.885
_shelx_estimated_absorpt_t_max   0.971
_shelx_res_checksum              62374