Copper-catalyzed radical reaction of N-tosylhydrazones: stereoselective synthesis of (e)-vinyl sulfones.
Mao, Shuai; Gao, Ya-Ru; Zhu, Xue-Qing; Guo, Dong-Dong; Wang, Yong-Qiang; Organic letters 17 (2015) 1692–1695; doi:10.1021/acs.orglett.5b00461

data_1518991
_publ_section_title
;
 Copper-catalyzed radical reaction of N-tosylhydrazones: stereoselective
 synthesis of (e)-vinyl sulfones.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1692
_journal_page_last               1695
_journal_paper_doi               10.1021/acs.orglett.5b00461
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C21 H17 F O2 S'
_chemical_formula_weight         352.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.253(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.402(3)
_cell_length_b                   5.7820(11)
_cell_length_c                   24.377(5)
_cell_measurement_reflns_used    923
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.96
_cell_measurement_theta_min      2.79
_cell_volume                     1720.1(6)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7284
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.9729
_exptl_absorpt_correction_T_min  0.9275
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0063(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.0238P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1302
_reflns_number_gt                1995
_reflns_number_total             3041
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00461_si_003.cif
_cod_data_source_block           xb7513_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1720.2(6)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1518991