Transition-metal-free radical cleavage of a hydrazonyl N–S bond: tosyl radical-initiated cascade C(sp3)–OAr cleavage, sulfonyl rearrangement and atropisomeric cyclopropanation
Chen, Yao-Zhong; Liu, Teng; Zhu, Jie; Zhang, Hui; Wu, Lei; Organic Chemistry Frontiers 5 (2018) 3567–; doi:10.1039/C8QO00873F

data_1554431
_publ_section_title
;
 Transition-metal-free radical cleavage of a hydrazonyl N--S bond: tosyl
 radical-initiated cascade C(sp3)--OAr cleavage, sulfonyl rearrangement
 and atropisomeric cyclopropanation
;
_journal_issue                   24
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3567
_journal_paper_doi               10.1039/C8QO00873F
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C36 H37 O4 P S'
_chemical_formula_sum            'C36 H37 O4 P S'
_chemical_formula_weight         596.68
_chemical_name_systematic
'(E)-(1-(2-cyclopropyl-3-tosylprop-1-en-1-yl)-2-(4-methoxyphenyl)-2-methylcyclopropyl)diphenylphosphine oxide'
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-09-12 deposited with the CCDC.
2018-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.555(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7333(10)
_cell_length_b                   32.515(5)
_cell_length_c                   11.3552(17)
_cell_measurement_reflns_used    7823
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.47
_cell_measurement_theta_min      2.19
_cell_volume                     3221.3(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            32918
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.594
_diffrn_reflns_theta_min         2.334
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6984
_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    1.230
_exptl_crystal_description       needle
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         7225
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+0.5266P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1417
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3918
_reflns_number_total             7225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00873f2.cif
_cod_data_source_block           cyz170801
_cod_original_cell_volume        3221.2(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1554431
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              71197
_shelx_hkl_checksum              16252