Rhodium(III)-Catalyzed Diverse [4+1] Annulation of Arenes with 1,3-Enynes via sp3/sp2 C-H Activation and 1,4-Rhodium Migration
Bai, Da-Chang; xia, jintao; song, fangfang; li, xueyan; Liu, Bingxian; liu, lihong; zheng, guangfan; Yang, Xifa; Sun, Jiaqiong; Li, Xingwei; Chemical Science  (2019) –; doi:10.1039/C9SC00545E

data_1550658
_publ_section_title
;
 Rhodium(III)-Catalyzed Diverse [4+1] Annulation of Arenes with 1,3-Enynes
 via sp3/sp2 C-H Activation and 1,4-Rhodium Migration
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00545E
_journal_year                    2019
_chemical_formula_moiety         'F6 P, C20 H20 N'
_chemical_formula_sum            'C20 H20 F6 N P'
_chemical_formula_weight         419.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-08-10
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2018-08-11 deposited with the CCDC.    2019-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.0040(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.90880(10)
_cell_length_b                   16.7762(3)
_cell_length_c                   13.3993(2)
_cell_measurement_reflns_used    8404
_cell_measurement_temperature    296.6(4)
_cell_measurement_theta_max      71.9380
_cell_measurement_theta_min      5.2580
_cell_volume                     1965.78(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.6(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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    -52.00  32.00   1.00    1.00    --  -35.45  57.00 -30.00   84
  2  \w    -32.00  62.00   1.00    1.00    --   35.45 -77.00   0.00   94
  3  \w     23.00  89.00   1.00    1.00    --   35.45-125.00-120.00   66
  4  \w      1.00  74.00   1.00    1.00    --   35.45 -99.00-180.00   73
  5  \w     23.00  89.00   1.00    1.00    --   35.45-125.00  30.00   66
  6  \w     19.00 103.00   1.00    1.00    --   35.45  57.00 120.00   84
  7  \w      1.00  74.00   1.00    1.00    --   35.45 -99.00-120.00   73
  8  \w    -32.00  62.00   1.00    1.00    --   35.45 -77.00-120.00   94
  9  \w     23.00  89.00   1.00    1.00    --   35.45-125.00 -60.00   66
 10  \w      6.00 107.00   1.00    1.00    --   35.45  19.00 -30.00  101
 11  \w      6.00 107.00   1.00    1.00    --   35.45  19.00 -30.00  101
 12  \w     42.00 127.00   1.00    1.17    --  108.69 -61.00 -60.00   85
 13  \w     91.00 177.00   1.00    1.17    --  108.69  45.00  30.00   86
 14  \w     91.00 177.00   1.00    1.17    --  108.69  45.00  90.00   86
 15  \w    100.00 178.00   1.00    1.17    --  108.69 111.00 -30.00   78
 16  \w     39.00 109.00   1.00    1.17    --  108.69 -95.00 -60.00   70
 17  \w     39.00 130.00   1.00    1.17    --  108.69 -30.00 -90.00   91
 18  \w     91.00 176.00   1.00    1.17    --  108.69  61.00  60.00   85
 19  \w     57.00 151.00   1.00    1.17    --  108.69 178.00-120.00   94
 20  \w     19.00 103.00   1.00    1.00    --   35.45  57.00-150.00   84
 21  \w    -32.00  52.00   1.00    1.00    --   35.45 -57.00  60.00   84
 22  \w      9.00 103.00   1.00    1.00    --   35.45  77.00 -90.00   94
 23  \w      9.00 103.00   1.00    1.00    --   35.45  77.00  90.00   94
 24  \w      9.00 103.00   1.00    1.00    --   35.45  77.00   0.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0146707000
_diffrn_orient_matrix_UB_12      0.0828965000
_diffrn_orient_matrix_UB_13      -0.0466939000
_diffrn_orient_matrix_UB_21      0.1704600000
_diffrn_orient_matrix_UB_22      0.0025450000
_diffrn_orient_matrix_UB_23      0.0504412000
_diffrn_orient_matrix_UB_31      0.0419163000
_diffrn_orient_matrix_UB_32      -0.0394236000
_diffrn_orient_matrix_UB_33      -0.0948496000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15460
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.295
_diffrn_reflns_theta_min         4.271
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.801
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0720
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1232P)^2^+0.8684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2065
_refine_ls_wR_factor_ref         0.2163
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3174
_reflns_number_total             3818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00545e2.cif
_cod_data_source_block           bdc-20180810
_cod_database_code               1550658
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C1 O1 N1 H1'
_shelx_estimated_absorpt_t_max   0.738
_shelx_estimated_absorpt_t_min   0.548
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Ternary CH refined with riding coordinates:
 C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C25(H25), C12(H12), C17(H17), C20(H20), C15(H15), C13(H13),
 C14(H14), C19(H19), C18(H18)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_shelx_res_checksum              46977
_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 6.834
_oxdiff_exptl_absorpt_empirical_full_min 0.655