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_4037897
_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         'C10 H10 O4'
_chemical_formula_sum            'C10 H10 O4'
_chemical_formula_weight         194.18
_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                117.17(2)
_cell_angle_beta                 100.016(17)
_cell_angle_gamma                90.347(15)
_cell_formula_units_Z            4
_cell_length_a                   7.6463(11)
_cell_length_b                   11.753(2)
_cell_length_c                   12.203(3)
_cell_measurement_reflns_used    3851
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.2950
_cell_measurement_theta_min      3.5140
_cell_volume                     956.2(4)
_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 0.992
_diffrn_measured_fraction_theta_max 0.991
_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      4.00  47.00   0.50   30.00    --    3.51-113.00 174.00   86
  2  \w     -7.00  28.00   0.50   30.00    --   -3.82-113.00 174.00   70
  3  \w    -57.00 -32.00   0.50   30.00    --    3.51 -57.00 -60.00   50
  4  \w    -14.00  38.00   0.50   30.00    --    3.51 -99.00  90.00  104
  5  \w    -16.00  15.00   0.50   30.00    --    3.51 -57.00 -60.00   62
  6  \w    -17.00  39.00   0.50   30.00    --    3.51 -99.00   0.00  112
  7  \w     14.00  68.00   0.50   30.00    --    3.51  38.00  90.00  108
  8  \w    -20.00  32.00   0.50   30.00    --   -3.82 -99.00 -90.00  104
  9  \w      4.00  30.00   0.50   30.00    --   -3.82 -99.00-120.00   52
 10  \w    -20.00   9.00   0.50   30.00    --   -3.82 -99.00-150.00   58
 11  \w    -20.00   5.00   0.50   30.00    --   -3.82 -99.00 120.00   50
 12  \w     -6.00  21.00   0.50   30.00    --   -3.82  38.00 150.00   54
 13  \w     -7.00  61.00   0.50   30.00    --   -3.82  38.00  30.00  136
 14  \w    -13.00  53.00   0.50   30.00    --   -3.82  57.00 -60.00  132
;
_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      -0.0424294000
_diffrn_orient_matrix_UB_12      0.0218588000
_diffrn_orient_matrix_UB_13      0.0523859000
_diffrn_orient_matrix_UB_21      0.0826074000
_diffrn_orient_matrix_UB_22      0.0046294000
_diffrn_orient_matrix_UB_23      0.0394348000
_diffrn_orient_matrix_UB_31      0.0180846000
_diffrn_orient_matrix_UB_32      0.0643799000
_diffrn_orient_matrix_UB_33      0.0121371000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0991
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16140
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.314
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73432
_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 whiteish white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.003
_exptl_crystal_size_mid          0.002
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0826
_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^)+(0.1720P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2479
_refine_ls_wR_factor_ref         0.2708
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2442
_reflns_number_total             3888
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03266_si_003.cif
_cod_data_source_block           ak-3-389
_cod_depositor_comments
;

2020-04-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        956.1(4)
_cod_original_formula_moiety     '2(C10 H10 O4)'
_cod_original_formula_sum        'C20 H20 O8'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     388.36
_cod_database_code               4037897
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C40 H40 O16 '
_diffrn_oxdiff_ac3_digest_frames
;
01b6f71d4b6b3276510b2195293541d17a00025b303
;
_diffrn_oxdiff_ac3_digest_hkl
;
01e7056269e636143bc887a267b9ece94c3f6f
;
_reflns_odcompleteness_completeness 99.41
_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:
 C00F(H00F), C00M(H00M)
2.b Idealised Me refined as rotating group:
 C00N(H00A,H00B,H00C), C00O(H00D,H00E,H00G), C00P(H00H,H00I,H00J), C00Q(H00K,
 H00L,H00N), C00R(H00O,H00P,H00Q), C00S(H00R,H00S,H00T)
;
_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 2.646
_oxdiff_exptl_absorpt_empirical_full_min 0.525