Acid-mediated sulfonylation of arylethynylene bromides with sodium arylsulfinates: synthesis of (E)-1,2-bis(arylsulfonyl)ethylenes and arylacetylenic sulfones
Dai, Chenshu; Wang, Junqi; Deng, Siqi; Zhou, Candong; Zhang, Wenhe; Zhu, Qiuhua; Tang, Xiaodong; RSC Adv. 7 (2017) 36112–; doi:10.1039/C7RA07105A

data_7228712
_publ_section_title
;
 Acid-mediated sulfonylation of arylethynylene bromides with sodium
 arylsulfinates: synthesis of (E)-1,2-bis(arylsulfonyl)ethylenes and
 arylacetylenic sulfones
;
_journal_issue                   57
_journal_name_full               'RSC Adv.'
_journal_page_first              36112
_journal_paper_doi               10.1039/C7RA07105A
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H20 O4 S2'
_chemical_formula_sum            'C22 H20 O4 S2'
_chemical_formula_weight         412.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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_date             2016-09-02
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2016-09-02 deposited with the CCDC.
2017-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8674(3)
_cell_length_b                   13.0958(6)
_cell_length_c                   22.6828(11)
_cell_measurement_reflns_used    9720
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.242
_cell_measurement_theta_min      3.375
_cell_volume                     2039.96(16)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20278
_diffrn_reflns_theta_full        68.30
_diffrn_reflns_theta_max         68.30
_diffrn_reflns_theta_min         5.16
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.578
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.2959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1425 before and 0.0735 after correction.
The Ratio of minimum to maximum transmission is 0.3929.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.069(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0569P)^2^+0.1956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                3642
_reflns_number_total             3677
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ra07105a2.cif
_cod_data_source_block           cu_0901nfyk_0m
_cod_database_code               7228712
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C25(H25A,H25B,H25C)
;
_olex2_submission_special_instructions 'No special instructions were received'