Regiocontrolled Synthesis of α-Sulfonylmethyl o-Nitrostyrenes via ZnI2-Mediated Sulfonylation and AgNO2/Pd(PPh3)4-Promoted o-Nitration.
Chang, Meng-Yang; Chen, Han-Yu; Wang, Heui-Sin; The Journal of organic chemistry 82 (2017) 10601–10610; doi:10.1021/acs.joc.7b02311

data_4032902
_publ_section_title
;
 Regiocontrolled Synthesis of \a-Sulfonylmethyl o-Nitrostyrenes via
 ZnI2-Mediated Sulfonylation and AgNO2/Pd(PPh3)4-Promoted o-Nitration.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10601
_journal_page_last               10610
_journal_paper_doi               10.1021/acs.joc.7b02311
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C10 H11 N O4 S'
_chemical_formula_weight         241.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                80.149(2)
_cell_angle_beta                 78.645(2)
_cell_angle_gamma                89.534(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1934(7)
_cell_length_b                   7.9479(7)
_cell_length_c                   9.7888(9)
_cell_measurement_reflns_used    5973
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.4424
_cell_measurement_theta_min      2.8893
_cell_volume                     540.42(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_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  0.0149
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8634
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.442
_diffrn_reflns_theta_min         2.889
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.9251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
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_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0288P)^2^+0.3611P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2093
_reflns_number_total             2206
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02311_si_001.cif
_cod_data_source_block           mo_161239LT_0m_a_4c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032901--4032905.cif.
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_cod_database_code               4032902
_shelxl_version_number           2014/6
_shelx_res_checksum              65848
_shelx_hkl_checksum              11070