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_4032904
_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            'C15 H13 Cl O3 S'
_chemical_formula_weight         308.76
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
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_cell_angle_beta                 90.107(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.676(2)
_cell_length_b                   9.256(4)
_cell_length_c                   27.339(12)
_cell_measurement_reflns_used    1691
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.2377
_cell_measurement_theta_min      2.6576
_cell_volume                     1436.3(10)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
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_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.973
_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  0.0595
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
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_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9517
_diffrn_reflns_point_group_measured_fraction_full 0.987
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.533
_diffrn_reflns_theta_min         2.323
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.6960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Acicular
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.20
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1330
_refine_ls_R_factor_gt           0.0676
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+1.1987P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1640
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1663
_reflns_number_total             2910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02311_si_001.cif
_cod_data_source_block           140301_6c
_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.
;
_cod_original_cell_volume        1436.2(10)
_cod_database_code               4032904
_shelxl_version_number           2013-4
_shelx_res_checksum              10615
_shelx_hkl_checksum              55542