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_1518992
_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            'C16 H16 O2 S'
_chemical_formula_weight         272.35
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7471(8)
_cell_length_b                   8.0541(11)
_cell_length_c                   31.351(4)
_cell_measurement_reflns_used    1072
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.04
_cell_measurement_theta_min      2.61
_cell_volume                     1451.2(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            7317
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.9548
_exptl_absorpt_correction_T_min  0.9260
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0442P)^2^+0.0939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                1810
_reflns_number_total             2575
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00461_si_004.cif
_cod_data_source_block           xb7439_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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        1451.1(3)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1518992