Direct vicinal difunctionalization of alkynes through trifluoromethylation and aminosulfonylation via insertion of sulfur dioxide under catalyst-free conditions
Li, Yuewen; Xiang, Yuanchao; Li, Zhiming; Wu, Jie; Organic Chemistry Frontiers 3 (2016) 1493–; doi:10.1039/C6QO00434B

data_1553518
_publ_section_title
;
 Direct vicinal difunctionalization of alkynes through
 trifluoromethylation and aminosulfonylation via insertion of sulfur
 dioxide under catalyst-free conditions
;
_journal_issue                   11
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1493
_journal_paper_doi               10.1039/C6QO00434B
_journal_volume                  3
_journal_year                    2016
_chemical_formula_sum            'C14 H17 F3 N2 O3 S'
_chemical_formula_weight         350.35
_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'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc1lvyhw
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-06-15 deposited with the CCDC.
2016-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.599(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.849(5)
_cell_length_b                   10.773(6)
_cell_length_c                   17.758(9)
_cell_measurement_reflns_used    974
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.369
_cell_measurement_theta_min      2.601
_cell_volume                     1692.2(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7549
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         2.211
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3295
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0680
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.1134P)^2^] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1757
_refine_ls_wR_factor_ref         0.1857
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2000
_reflns_number_total             3295
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00434b2.cif
_cod_data_source_block           a51117a
_cod_original_cell_volume        1692.3(15)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1553518
_shelx_estimated_absorpt_t_min   0.895
_shelx_estimated_absorpt_t_max   0.933
_shelxl_version_number           2013-2
_shelx_res_checksum              429
_shelx_hkl_checksum              31284