Cp*Rh(III)-catalyzed regioselective cyclization of aromatic amides with allenes.
Liu, Jing; Liu, Deng-Yin; Yang, Qian; Zeng, Yao-Fu; Wang, Xiao-Li; Wang, Peng-Fei; Ruan, Yu-Jun; Wen, Miao-Miao; Zhang, Shang-Shi; Du, Li-da; Liu, Xu-Ge; Chemical communications (Cambridge, England) 60 (2024) 598–601; doi:10.1039/d3cc05342c

data_7132448
_publ_section_title
;
 Cp*Rh(III)-catalyzed regioselective cyclization of aromatic amides with
 allenes.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              598
_journal_page_last               601
_journal_paper_doi               10.1039/d3cc05342c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C20 H15 Br N2 O3'
_chemical_formula_sum            'C20 H15 Br N2 O3'
_chemical_formula_weight         411.25
_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             2023-05-31
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-06-25 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.638(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3629(4)
_cell_length_b                   17.7232(15)
_cell_length_c                   18.1847(18)
_cell_measurement_reflns_used    2297
_cell_measurement_temperature    150.00(18)
_cell_measurement_theta_max      73.6300
_cell_measurement_theta_min      3.3390
_cell_volume                     1722.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (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      150.00(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_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    -60.00   3.00   1.00    1.50    --  -40.92  57.00 120.00   63
  2  \w      7.00  32.00   1.00    1.50    --  -40.92  57.00 120.00   25
  3  \w     70.00  97.00   1.00    1.50    --   40.92-125.00 -90.00   27
  4  \w     88.00 113.00   1.00    2.00    --  107.58-104.00 -93.00   25
  5  \w     72.00 137.00   1.00    2.00    --  107.58 -77.00-180.00   65
  6  \w     41.00  71.00   1.00    2.00    --  107.58 -94.00-180.00   30
  7  \w     32.00 135.00   1.00    2.00    --  107.58 -30.00 -90.00  103
  8  \w    126.00 178.00   1.00    2.00    --  107.58  61.00-120.00   52
  9  \w    102.00 166.00   1.00    2.00    --  107.58  77.00 -90.00   64
 10  \w     35.00  61.00   1.00    2.00    --  107.58-104.00 -93.00   26
 11  \w     36.00 122.00   1.00    2.00    --  107.58-125.00 120.00   86
 12  \w   -115.00 -19.00   1.00    1.50    --  -40.92 -37.00 -30.00   96
 13  \w   -106.00 -76.00   1.00    1.50    --  -41.23 -37.00 120.00   30
 14  \w   -109.00 -64.00   1.00    1.50    --  -41.23 -57.00-120.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0501926000
_diffrn_orient_matrix_UB_12      -0.0603894000
_diffrn_orient_matrix_UB_13      -0.0603509000
_diffrn_orient_matrix_UB_21      0.0869910000
_diffrn_orient_matrix_UB_22      -0.0619791000
_diffrn_orient_matrix_UB_23      0.0556600000
_diffrn_orient_matrix_UB_31      -0.2701064000
_diffrn_orient_matrix_UB_32      -0.0086507000
_diffrn_orient_matrix_UB_33      0.0218635000
_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  0.1122
_diffrn_reflns_av_unetI/netI     0.1316
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6971
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.912
_diffrn_reflns_theta_min         3.488
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.452
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.675
_refine_diff_density_min         -1.038
_refine_diff_density_rms         0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     363
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0913
_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^)+(0.1795P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2469
_refine_ls_wR_factor_ref         0.2834
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2494
_reflns_number_total             3388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05342c2.cif
_cod_data_source_block           br0525
_cod_depositor_comments
'Adding full bibliography for 7132447--7132448.cif.'
_cod_original_cell_volume        1722.7(3)
_cod_database_code               7132448
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq, Uanis(Br1) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C2) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(N1)
\\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C8) \\sim Ueq,
Uanis(O1) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim
Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O2)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq,
Uanis(C20) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C18)
\\sim Ueq, : with sigma of 0.002 and sigma for terminal atoms of 0.004
3. Rigid body (RIGU) restrains
 Br1, O1, O2, O3, N1, N2, H2, C1, C2, H2A, C3, H3, C4, C5, H5, C6, C7, H7, C8,
 C9, C10, H10, C11, C12, H12A, H12B, C13, C14, H14A, H14B, C15, C16, H16, C17,
 H17, C18, H18, C19, H19, C20, H20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C5(H5), C7(H7), C10(H10), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              25286
_shelx_hkl_checksum              85408
_olex2_date_sample_data_collection 2023-05-25
_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 3.385
_oxdiff_exptl_absorpt_empirical_full_min 0.343