Catalyst-free room-temperature decarboxylative tri- or tetrafunctionalization of alkynyl carboxylic acids with N-fluorobenzenesulfonimide (NFSI) and diselenides
Wang, Ying-chun; Liu, Li-qiu; Wang, Guang-mang; Ouyang, Hui; Li, You-ji; Green Chemistry 20 (2018) 604–; doi:10.1039/C7GC03267F

data_7229846
_publ_section_title
;
 Catalyst-free room-temperature decarboxylative tri- or
 tetrafunctionalization of alkynyl carboxylic acids with
 N-fluorobenzenesulfonimide (NFSI) and diselenides
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              604
_journal_paper_doi               10.1039/C7GC03267F
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C32 H25 N O4 S2 Se2'
_chemical_formula_sum            'C32 H25 N O4 S2 Se2'
_chemical_formula_weight         709.57
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-02-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-09-27 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                110.126(6)
_cell_angle_beta                 99.341(5)
_cell_angle_gamma                93.707(6)
_cell_formula_units_Z            2
_cell_length_a                   9.3039(6)
_cell_length_b                   11.2838(9)
_cell_length_c                   15.3630(8)
_cell_measurement_reflns_used    5410
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1340
_cell_measurement_theta_min      3.8690
_cell_volume                     1481.60(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -91.00   7.00   1.00    5.00    --  -18.55 -38.00   0.00   98
  2  \w    -89.00  12.00   1.00    5.00    --  -18.55 -77.00-120.00  101
  3  \w    -20.00  61.00   1.00    5.00    --   18.86 -99.00 150.00   81
  4  \w      6.00  79.00   1.00    5.00    --   18.86-130.00  56.00   73
  5  \w    -25.00  92.00   1.00    5.00    --   18.86  19.00-150.00  117
  6  \w    -87.00   3.00   1.00    5.00    --  -18.55 -57.00 -90.00   90
  7  \w    -95.00 -34.00   1.00    5.00    --  -18.55 178.00 150.00   61
  8  \w     35.00  60.00   1.00    5.00    --   18.86 178.00 150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0288434000
_diffrn_orient_matrix_UB_12      -0.0584816000
_diffrn_orient_matrix_UB_13      0.0021031000
_diffrn_orient_matrix_UB_21      -0.0137708000
_diffrn_orient_matrix_UB_22      -0.0275812000
_diffrn_orient_matrix_UB_23      -0.0500710000
_diffrn_orient_matrix_UB_31      0.0710665000
_diffrn_orient_matrix_UB_32      -0.0194514000
_diffrn_orient_matrix_UB_33      0.0019827000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18341
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.41
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.973
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         6045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+0.3304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                4570
_reflns_number_total             6045
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7gc03267f2.cif
_cod_data_source_block           20161123-pym-hy-sm-14aaaa
_cod_depositor_comments
'Adding full bibliography for 7229845--7229846.cif.'
_cod_original_cell_volume        1481.59(17)
_cod_database_code               7229846
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C15(H15), C17(H17), C20(H20), C24(H24), C27(H27),
 C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C35(H35), C37(H37), C38(H38),
  C44(H44), C47(H47), C48(H48), C49(H49), C54(H54), C42(H42), C(H), C3(H3),
 C7(H7), C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.790
_oxdiff_exptl_absorpt_empirical_full_min 0.667