Magnetically separable nano-copper catalyzed unprecedented stereoselective synthesis of E-vinyl sulfones from tosylmethyl isocyanide and alkynes: TosMIC as a source of the sulfonyl group
Phanindrudu, Mandalaparthi; Tiwari, Dipak Kumar; Sridhar, B.; Likhar, Pravin R.; Tiwari, Dharmendra Kumar; Organic Chemistry Frontiers 3 (2016) 795–; doi:10.1039/C6QO00063K

data_1553444
_publ_section_title
;
 Magnetically separable nano-copper catalyzed unprecedented
 stereoselective synthesis of E-vinyl sulfones from tosylmethyl isocyanide
 and alkynes: TosMIC as a source of the sulfonyl group
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              795
_journal_paper_doi               10.1039/C6QO00063K
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C16 H16 O3 S'
_chemical_formula_sum            'C16 H16 O3 S'
_chemical_formula_weight         288.35
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-02-02 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9262(4)
_cell_length_b                   8.0475(5)
_cell_length_c                   31.957(2)
_cell_measurement_reflns_used    3190
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      19.61
_cell_measurement_theta_min      2.55
_cell_volume                     1524.06(17)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            16245
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.241
_diffrn_reflns_theta_min         2.549
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SABABS; Bruker,2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 658 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0663
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0923P)^2^+0.1152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1648
_refine_ls_wR_factor_ref         0.1804
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2225
_reflns_number_total             3077
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00063k2.cif
_cod_data_source_block           ay66m
_cod_original_cell_volume        1524.08(17)
_cod_database_code               1553444
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              48955
_shelx_hkl_checksum              57969