Rhodium(III)-catalysed decarboxylative C-H functionalization of isoxazoles with alkenes and sulfoxonium ylides.
Yugandar, Somaraju; Morita, Taiki; Nakamura, Hiroyuki; Organic & biomolecular chemistry 18 (2020) 8625–8628; doi:10.1039/d0ob02027c

data_7157739
_publ_section_title
;
 Rhodium(III)-catalysed decarboxylative C-H functionalization of
 isoxazoles with alkenes and sulfoxonium ylides.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8625
_journal_page_last               8628
_journal_paper_doi               10.1039/d0ob02027c
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C18 H14 Cl N O3'
_chemical_formula_sum            'C18 H14 Cl N O3'
_chemical_formula_weight         327.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-28 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.634(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.8793(17)
_cell_length_b                   7.7831(4)
_cell_length_c                   12.7135(7)
_cell_measurement_reflns_used    4335
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      75.8360
_cell_measurement_theta_min      3.5290
_cell_volume                     2950.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.945
_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    -20.00   5.00   0.50    0.05    --  -45.95  10.00 100.00   50
  2  \w    -69.00 -43.00   0.50    0.20    -- -102.00  61.00 120.00   52
  3  \w   -111.00 -29.00   0.50    0.20    -- -102.00 125.00  90.00  164
  4  \w    -68.00 -32.00   0.50    0.20    -- -102.00  61.00 -60.00   72
  5  \w    -21.00  21.00   0.50    0.05    --  -45.95  19.00-150.00   84
  6  \w    -14.00  26.00   0.50    0.05    --   45.95 -10.00 -73.00   80
  7  \w     46.00  90.00   0.50    0.20    --  104.61 -94.00-150.00   88
  8  \w     34.00 110.00   0.50    0.20    --  104.61-125.00-150.00  152
  9  \w     33.00  73.00   0.50    0.20    --  104.61 -61.00 -30.00   80
 10  \w     33.00 118.00   0.50    0.05    --   45.95  10.00 100.00  170
 11  \w     89.00 173.00   0.50    0.20    --  104.61  10.00 100.00  168
 12  \w     99.00 154.00   0.50    0.20    --  104.61  45.00 -30.00  110
 13  \w     27.00  86.00   0.50    0.05    --   45.95-125.00 120.00  118
 14  \w    -67.00 -35.00   0.50    0.20    -- -102.00  77.00-150.00   64
 15  \w    -97.00 -71.00   0.50    0.05    --  -45.95 -10.00 -73.00   52
 16  \w   -113.00 -88.00   0.50    0.20    -- -102.00 -10.00 -73.00   50
 17  \w   -116.00 -85.00   0.50    0.20    -- -102.00 -61.00-120.00   62
 18  \w   -104.00 -74.00   0.50    0.05    --  -45.95-125.00-150.00   60
 19  \w   -140.00-107.00   0.50    0.20    -- -102.00 -30.00-150.00   66
 20  \w   -173.00-130.00   0.50    0.20    -- -102.00 -61.00-120.00   86
 21  \w   -101.00 -74.00   0.50    0.20    -- -102.00  77.00-150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8475
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.193
_diffrn_reflns_theta_min         5.876
_exptl_absorpt_coefficient_mu    2.427
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0811P)^2^+1.5765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1253
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2639
_reflns_number_total             2914
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02027c2.cif
_cod_data_source_block           crl37621
_cod_depositor_comments          'Adding full bibliography for 7157739.cif.'
_cod_database_code               7157739
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.793
_shelx_estimated_absorpt_t_min   0.444
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C16(H16), C14(H14), C17(H17), C13(H13), C2(H2), C6(H6), C3(H3), C5(H5)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              82975
_shelx_hkl_checksum              75792
_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
;