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_1567038
_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         'C29 H22 Cl N O'
_chemical_formula_sum            'C29 H22 Cl N O'
_chemical_formula_weight         435.92
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-01-21 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.828(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.7731(3)
_cell_length_b                   7.1332(2)
_cell_length_c                   19.2367(4)
_cell_measurement_reflns_used    5461
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9580
_cell_measurement_theta_min      4.0470
_cell_volume                     2224.95(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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 0.996
_diffrn_measured_fraction_theta_max 0.969
_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    -73.00  24.00   1.00    1.61    --  -35.62  96.00  83.00   97
  2  \w     -2.00  73.00   1.00    1.61    --   35.62 -96.00 -25.00   75
  3  \w     38.00 109.00   1.00    6.44    --  107.12 -96.00 -25.00   71
  4  \w    104.00 177.00   1.00    6.44    --  107.12  96.00  83.00   73
  5  \w   -107.00 -42.00   1.00    1.61    --  -35.62-178.00-120.00   65
  6  \w   -103.00 -22.00   1.00    1.61    --  -35.62 -57.00 120.00   81
  7  \w    -61.00  19.00   1.00    1.61    --  -35.62  77.00-120.00   80
  8  \w     73.00 107.00   1.00    1.61    --   35.62-178.00 -90.00   34
  9  \w     50.00  75.00   1.00    6.44    --  107.12 -30.00 150.00   25
 10  \w     82.00 129.00   1.00    6.44    --  107.12 -30.00 150.00   47
 11  \w     38.00 101.00   1.00    6.44    --  107.12-111.00 -60.00   63
 12  \w     88.00 113.00   1.00    6.44    --  107.12-111.00  60.00   25
 13  \w    101.00 177.00   1.00    6.44    --  107.12 111.00-180.00   76
 14  \w    101.00 128.00   1.00    6.44    --  107.12 111.00-120.00   27
 15  \w    145.00 170.00   1.00    6.44    --  107.12 111.00-120.00   25
 16  \w     38.00  67.00   1.00    6.44    --  107.12-111.00  60.00   29
 17  \w    148.00 174.00   1.00    6.44    --  107.12  61.00 -30.00   26
 18  \w    107.00 133.00   1.00    6.44    --  107.12  61.00 -30.00   26
 19  \w     42.00 122.00   1.00    6.44    --  107.12 -45.00  30.00   80
 20  \w     90.00 167.00   1.00    6.44    --  107.12  45.00-180.00   77
;
_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      -0.0175734000
_diffrn_orient_matrix_UB_12      -0.1758431000
_diffrn_orient_matrix_UB_13      -0.0480045000
_diffrn_orient_matrix_UB_21      -0.0356353000
_diffrn_orient_matrix_UB_22      -0.0993472000
_diffrn_orient_matrix_UB_23      0.0564861000
_diffrn_orient_matrix_UB_31      -0.0863145000
_diffrn_orient_matrix_UB_32      0.0767250000
_diffrn_orient_matrix_UB_33      -0.0369223000
_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  0.0204
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10420
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.966
_diffrn_reflns_theta_min         4.050
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (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    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0493P)^2^+1.2823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3517
_reflns_number_total             4246
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc02205b2.cif
_cod_data_source_block           slc-20220107
_cod_depositor_comments
'Adding full bibliography for 1567038--1567039.cif.'
_cod_database_code               1567038
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 O1 Cl1 N1'
_shelx_estimated_absorpt_t_max   0.850
_shelx_estimated_absorpt_t_min   0.850
_reflns_odcompleteness_completeness 99.72
_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:
 C7(H7A,H7B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C22(H22), C12(H12), C15(H15), C2(H2), C28(H28), C13(H13), C24(H24),
 C25(H25), C32(H32), C3(H3), C23(H23), C31(H31), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              12025
_shelx_hkl_checksum              41441
_olex2_date_sample_data_collection 2022-01-07
_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 1.426
_oxdiff_exptl_absorpt_empirical_full_min 0.748