Rhodium(III)-Catalyzed C-H Activation: A Cascade Approach for the Regioselective Synthesis of Fused Heterocyclic Lactone Scaffolds.
Kumar, Anil; Prabhu, Kandikere Ramaiah; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03266

data_4037896
_publ_section_title
;
 Rhodium(III)-Catalyzed C-H Activation: A Cascade Approach for the
 Regioselective Synthesis of Fused Heterocyclic Lactone Scaffolds.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03266
_journal_year                    2020
_chemical_formula_moiety         'C14 H12 O4'
_chemical_formula_sum            'C14 H12 O4'
_chemical_formula_weight         244.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-26
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                112.818(5)
_cell_angle_beta                 94.908(4)
_cell_angle_gamma                92.972(4)
_cell_formula_units_Z            2
_cell_length_a                   5.3666(2)
_cell_length_b                   9.7979(5)
_cell_length_c                   12.3394(6)
_cell_measurement_reflns_used    4969
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.9150
_cell_measurement_theta_min      3.8120
_cell_volume                     593.29(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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     12.00  65.00   0.50   25.00    --    3.67-142.00-155.00  106
  2  \w      5.00  57.00   0.50   25.00    --    3.67-128.00  16.00  104
  3  \w    -20.00  40.00   0.50   25.00    --    3.67 -99.00-180.00  120
  4  \w    -66.00   9.00   0.50   25.00    --    3.67 -19.00 -90.00  150
  5  \w    -20.00  40.00   0.50   25.00    --    3.67 -99.00   0.00  120
  6  \w    -62.00   7.00   0.50   25.00    --    3.67 -38.00  30.00  138
  7  \w    -20.00  32.00   0.50   25.00    --   -3.98 -99.00-180.00  104
  8  \w    -14.00  32.00   0.50   25.00    --   -3.98 -99.00-120.00   92
  9  \w    -19.00  27.00   0.50   25.00    --   -3.98 -99.00  90.00   92
 10  \w     -8.00  51.00   0.50   25.00    --   -3.98  57.00-150.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0168081000
_diffrn_orient_matrix_UB_12      0.0412171000
_diffrn_orient_matrix_UB_13      -0.0354869000
_diffrn_orient_matrix_UB_21      -0.0385225000
_diffrn_orient_matrix_UB_22      -0.0649180000
_diffrn_orient_matrix_UB_23      -0.0516716000
_diffrn_orient_matrix_UB_31      -0.1264242000
_diffrn_orient_matrix_UB_32      0.0175647000
_diffrn_orient_matrix_UB_33      0.0034332000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10224
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.357
_diffrn_reflns_theta_min         3.407
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       needle
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.002
_exptl_crystal_size_mid          0.001
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0600P)^2^+0.0760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1210
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1871
_reflns_number_total             2421
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03266_si_002.cif
_cod_data_source_block           pcr_ak_3_382
_cod_database_code               4037896
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C14 H12 O4'
_diffrn_oxdiff_ac3_digest_frames
;
015bd6f35c3acf9ee5c56a7f99b6ed42fc00025b94e
;
_diffrn_oxdiff_ac3_digest_hkl
;
0149a52e9762e7ab5cab92cfbfecf0ec8b0dda
;
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00F(H00F)
2.b Idealised Me refined as rotating group:
 C00G(H00A,H00D,H00E), C00H(H00G,H00H,H00I), C00I(H00J,H00K,H00L)
;
_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 2.286
_oxdiff_exptl_absorpt_empirical_full_min 0.626