Electrochemistry-enabled Rh-catalyzed regioselective [4 + 1] and [4 + 2] cycloaddition of benzoic acid with alkynyl esters/amides
Chiu, Wei-Jung; Sun, Chung-Ming; Green Chemistry 26 (2024) 10996–11002; doi:10.1039/D4GC03753G

data_7249417
_publ_section_title
;
 Electrochemistry-enabled Rh-catalyzed regioselective [4 + 1] and [4 + 2]
 cycloaddition of benzoic acid with alkynyl esters/amides
;
_journal_issue                   21
_journal_name_full               'Green Chemistry'
_journal_page_first              10996
_journal_page_last               11002
_journal_paper_doi               10.1039/D4GC03753G
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C16 H18 O4'
_chemical_formula_sum            'C16 H18 O4'
_chemical_formula_weight         274.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-01-03 deposited with the CCDC.	2024-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.758(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7049(3)
_cell_length_b                   14.6860(3)
_cell_length_c                   8.72913(18)
_cell_measurement_reflns_used    5622
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.6280
_cell_measurement_theta_min      4.0270
_cell_volume                     1403.12(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.948
_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    -77.00 -52.00   0.50    0.06    --  -72.13  91.00-112.00   50
  2  \w    -76.00 -50.00   0.50    0.06    --  -75.32  91.00-112.00   52
  3  \w    -52.00 -19.00   0.50    0.06    --  -59.44  91.00-112.00   66
  4  \w    -92.00 -43.00   0.50    0.06    --  -75.32 111.00  30.00   98
  5  \w     78.00 106.00   0.50    0.06    --   56.25  15.00-180.00   56
  6  \w     47.00  74.00   0.50    0.06    --   56.25  15.00-180.00   54
  7  \w     50.00 133.00   0.50    0.06    --   83.87  15.00-120.00  166
  8  \w     62.00 106.00   0.50    0.06    --   56.25  15.00 -60.00   88
  9  \w     56.00 131.00   0.50    0.06    --   83.87  15.00 -30.00  150
 10  \w     42.00 120.00   0.50    0.06    --   75.94  15.00  90.00  156
 11  \w     56.00  85.00   0.50    0.06    --   83.87 -91.00 133.00   58
 12  \w     38.00  90.00   0.50    0.06    --   75.94-111.00 120.00  104
 13  \w     50.00  75.00   0.50    0.06    --   83.87-111.00  60.00   50
 14  \w     58.00  83.00   0.50    0.06    --   56.25-125.00  30.00   50
 15  \w     21.00  47.00   0.50    0.06    --   56.25-125.00  30.00   52
 16  \w     22.00  48.00   0.50    0.06    --   56.25 -91.00 133.00   52
 17  \w     52.00  91.00   0.50    0.06    --   83.87 -95.00 -60.00   78
 18  \w     46.00  76.00   0.50    0.06    --   75.94 -95.00 -90.00   60
 19  \w     47.00  83.00   0.50    0.06    --   83.87-111.00-150.00   72
 20  \w     34.00  82.00   0.50    0.06    --   75.94 -95.00-150.00   96
 21  \w     28.00  53.00   0.50    0.06    --   69.31 -91.00 133.00   50
 22  \w     48.00  77.00   0.50    0.06    --   75.94 -91.00 133.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0236149000
_diffrn_orient_matrix_UB_12      0.0945550000
_diffrn_orient_matrix_UB_13      -0.0592369000
_diffrn_orient_matrix_UB_21      -0.1386987000
_diffrn_orient_matrix_UB_22      0.0172669000
_diffrn_orient_matrix_UB_23      -0.0730862000
_diffrn_orient_matrix_UB_31      0.0042406000
_diffrn_orient_matrix_UB_32      0.0419583000
_diffrn_orient_matrix_UB_33      0.1637005000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9347
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.910
_diffrn_reflns_theta_min         4.039
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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    1.299
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.799
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0634P)^2^+1.1147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2351
_reflns_number_total             2744
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc03753g2.cif
_cod_data_source_block           230653lt_auto
_cod_depositor_comments
'Adding full bibliography for 7249417--7249418.cif.'
_cod_original_cell_volume        1403.13(5)
_cod_database_code               7249417
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.875
_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:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              43437
_shelx_hkl_checksum              21440
_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 1.204
_oxdiff_exptl_absorpt_empirical_full_min 0.823