Rhodium-catalyzed multiple C-H activation/highly <i>meta</i>-selective C-H amination between amidines and alkynes.
Xu, Fen; Song, Yuan-Yuan; Zhu, Wen-Jing; Liu, Chun-Sen; Lu, Ya-Zhou; Du, Miao; Chemical communications (Cambridge, England) 56 (2020) 11227–11230; doi:10.1039/d0cc04885b

data_7127075
_publ_section_title
;
 Rhodium-catalyzed multiple C-H activation/highly <i>meta</i>-selective
 C-H amination between amidines and alkynes.
;
_journal_issue                   76
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11227
_journal_page_last               11230
_journal_paper_doi               10.1039/d0cc04885b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         '0.31(C23 H26 Cl2 N2 Rh), 0.15(C14 H10)'
_chemical_formula_sum            'C9.23 H9.54 Cl0.62 N0.62 Rh0.31'
_chemical_formula_weight         182.58
_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             2019-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-26 deposited with the CCDC.	2020-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.679(2)
_cell_angle_gamma                90
_cell_formula_units_Z            13
_cell_length_a                   15.6342(3)
_cell_length_b                   7.29120(10)
_cell_length_c                   25.8878(5)
_cell_measurement_reflns_used    6762
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.6810
_cell_measurement_theta_min      5.5350
_cell_volume                     2917.21(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.965
_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    -33.00  22.00   1.00    1.16    --   40.80 -38.00  60.00   55
  2  \w     23.00  50.00   1.00    1.16    --   40.80-125.00  60.00   27
  3  \w     26.00  99.00   1.00    4.64    --  107.14 -95.00 150.00   73
  4  \w     84.00 116.00   1.00    4.64    --  107.14  30.00 -60.00   32
  5  \w     84.00 166.00   1.00    4.64    --  107.14  77.00 -60.00   82
  6  \w     97.00 178.00   1.00    4.64    --  107.14 125.00-180.00   81
  7  \w     94.00 169.00   1.00    4.64    --  107.14  61.00   0.00   75
  8  \w     68.00 139.00   1.00    4.64    --  107.14 -77.00-180.00   71
  9  \w    -70.00  35.00   1.00    1.16    --  -40.80  77.00 -90.00  105
 10  \w    -87.00 -13.00   1.00    1.16    --  -40.80 -57.00 120.00   74
;
_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      -0.0011200000
_diffrn_orient_matrix_UB_12      -0.1035969000
_diffrn_orient_matrix_UB_13      0.0517745000
_diffrn_orient_matrix_UB_21      -0.0267133000
_diffrn_orient_matrix_UB_22      -0.1771413000
_diffrn_orient_matrix_UB_23      -0.0306897000
_diffrn_orient_matrix_UB_31      0.0960020000
_diffrn_orient_matrix_UB_32      -0.0504233000
_diffrn_orient_matrix_UB_33      0.0014903000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10953
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.802
_diffrn_reflns_theta_min         3.454
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.854
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0448P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5135
_reflns_number_total             5691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04885b2.cif
_cod_data_source_block           syy-h4
_cod_depositor_comments
'Adding full bibliography for 7127071--7127077.cif.'
_cod_database_code               7127075
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_usercomment     'C H N'
_shelx_estimated_absorpt_t_max   0.302
_shelx_estimated_absorpt_t_min   0.280
_reflns_odcompleteness_completeness 99.95
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C26(H26), C7(H7), C30(H30), C18(H18), C27(H27),
 C5(H5), C20(H20), C22(H22), C6(H6), C28(H28), C21(H21), C23(H23), C29(H29)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C8(H8A,H8B,H8C), C14(H14A,H14B,H14C), C17(H17A,H17B,
 H17C), C16(H16A,H16B,H16C)
;
_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 3.191
_oxdiff_exptl_absorpt_empirical_full_min 0.539