RhodiumIII-catalyzed remote difunctionalization of arenes assisted by a relay directing group
Sun, Lincong; Zhao, Yuyao; Liu, Bingxian; Chang, Junbiao; Li, Xingwei; Chemical Science 13 (2022) 7347–7354; doi:10.1039/D2SC02205B

data_1567039
_publ_section_title
;
 RhodiumIII-catalyzed remote difunctionalization of arenes assisted by a
 relay directing group
;
_journal_issue                   24
_journal_name_full               'Chemical Science'
_journal_page_first              7347
_journal_page_last               7354
_journal_paper_doi               10.1039/D2SC02205B
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C25 H29 Cl N O Rh'
_chemical_formula_sum            'C25 H29 Cl N O Rh'
_chemical_formula_weight         497.85
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-03-15 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.5280(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.7457(2)
_cell_length_b                   7.72790(10)
_cell_length_c                   31.2170(4)
_cell_measurement_reflns_used    10466
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2630
_cell_measurement_theta_min      3.8060
_cell_volume                     4513.68(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_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 -16.00   1.00    1.00    --  -35.62  76.00  60.00   44
  2  \w     -2.00  32.00   1.00    1.00    --  -35.62  76.00  60.00   34
  3  \w      2.00  29.00   1.00    1.00    --   35.62 -76.00 -66.00   27
  4  \w     32.00  57.00   1.00    1.00    --   35.62  76.00  60.00   25
  5  \w     44.00 120.00   1.00    3.82    --  107.12 -76.00 -66.00   76
  6  \w     85.00 173.00   1.00    3.82    --  107.12  76.00  60.00   88
  7  \w    -97.00 -26.00   1.00    1.00    --  -35.62 -76.00 -66.00   71
  8  \w      2.00  72.00   1.00    1.00    --   35.62 -99.00-120.00   70
  9  \w     58.00 106.00   1.00    1.00    --   35.62 178.00  90.00   48
 10  \w      1.00  75.00   1.00    1.00    --   35.62 -99.00 120.00   74
 11  \w     85.00 124.00   1.00    3.82    --  107.12 -45.00  60.00   39
 12  \w    100.00 175.00   1.00    3.82    --  107.12 111.00   0.00   75
 13  \w     39.00  79.00   1.00    3.82    --  107.12 -45.00  60.00   40
 14  \w    118.00 166.00   1.00    3.82    --  107.12 111.00  30.00   48
 15  \w     84.00 124.00   1.00    3.82    --  107.12 -61.00 -30.00   40
 16  \w     81.00 107.00   1.00    3.82    --  107.12 -95.00-180.00   26
 17  \w     43.00 121.00   1.00    3.82    --  107.12 -30.00 -90.00   78
 18  \w     52.00 102.00   1.00    3.82    --  107.12 -95.00 150.00   50
;
_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      0.0433801000
_diffrn_orient_matrix_UB_12      -0.1664272000
_diffrn_orient_matrix_UB_13      -0.0062003000
_diffrn_orient_matrix_UB_21      -0.0207437000
_diffrn_orient_matrix_UB_22      0.0048473000
_diffrn_orient_matrix_UB_23      -0.0485224000
_diffrn_orient_matrix_UB_31      0.0668468000
_diffrn_orient_matrix_UB_32      0.1095009000
_diffrn_orient_matrix_UB_33      -0.0072923000
_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  0.0419
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            18072
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.506
_diffrn_reflns_theta_min         3.802
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.317
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
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    1.465
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.216
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         8597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+3.2270P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7449
_reflns_number_total             8597
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc02205b2.cif
_cod_data_source_block           slc-20220315
_cod_depositor_comments
;
Adding full bibliography for 1567038--1567039.cif.

2025-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C50 H58 Cl2 N2 O2 Rh2'
_cod_original_formula_weight         995.70
_cod_original_formula_moiety         '2(C25 H29 Cl N O Rh)'
_cod_original_formula_units_Z            4
_cod_database_code               1567039
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Rh1 Cl1 C1 O1 N1'
_shelx_estimated_absorpt_t_max   0.528
_shelx_estimated_absorpt_t_min   0.528
_reflns_odcompleteness_completeness 99.89
_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 Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C9(H9), C12(H12), C6(H6), C15(H15), C26(H26), C33(H33), C27(H27),
 C14(H14), C7(H7), C13(H13), C32(H32), C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C45(H45A,H45B,H45C), C44(H44A,H44B,H44C), C47(H47A,H47B,H47C), C46(H46A,H46B,
 H46C), C54(H54A,H54B,H54C), C55(H55A,H55B,H55C), C57(H57A,H57B,H57C), C48(H48A,
 H48B,H48C), C58(H58A,H58B,H58C), C56(H56A,H56B,H56C), C38(H38A,H38B,H38C),
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              89756
_shelx_hkl_checksum              39551
_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 2.365
_oxdiff_exptl_absorpt_empirical_full_min 0.363