Cu-Mediated Sulfonyl Radical-Enabled 5- exo-trig Cyclization of Alkenyl Aldehydes: Access to Sulfonylmethyl 1 H-Indenes.
Ni, Jiabin; Xue, Yu; Sun, Liping; Zhang, Ao; The Journal of organic chemistry 83 (2018) 4598–4605; doi:10.1021/acs.joc.8b00341

data_4034945
_publ_section_title
;
 Cu-Mediated Sulfonyl Radical-Enabled 5- exo-trig Cyclization of Alkenyl
 Aldehydes: Access to Sulfonylmethyl 1 H-Indenes.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4598
_journal_page_last               4605
_journal_paper_doi               10.1021/acs.joc.8b00341
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C16 H14 O2 S'
_chemical_formula_sum            'C16 H14 O2 S'
_chemical_formula_weight         270.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-12
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.02.02 svn.r3481 for OlexSys, GUI svn.r5470)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.016(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.299(3)
_cell_length_b                   10.924(4)
_cell_length_c                   14.783(5)
_cell_measurement_reflns_used    3578
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.369
_cell_measurement_theta_min      2.326
_cell_volume                     1327.1(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9223
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.519
_diffrn_reflns_theta_min         2.326
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1097 before and 0.0546 after correction. The Ratio of minimum to maximum transmission is 0.8750. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0845P)^2^+0.3455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1457
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2179
_reflns_number_total             2656
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00341_si_002.cif
_cod_data_source_block           mo_20180187-9216-43-19_0m
_cod_database_code               4034945
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.936
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C12(H12), C6(H6), C16(H16), C3(H3), C4(H4), C5(H5), C13(H13),
 C14(H14), C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'