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_7127076
_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         'C50 H32 N4 S2'
_chemical_formula_sum            'C50 H32 N4 S2'
_chemical_formula_weight         752.95
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                102.279(2)
_cell_angle_beta                 99.940(2)
_cell_angle_gamma                97.712(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8941(3)
_cell_length_b                   13.9468(4)
_cell_length_c                   16.4764(5)
_cell_measurement_reflns_used    7204
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.3570
_cell_measurement_theta_min      4.7900
_cell_volume                     2153.46(11)
_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 0.968
_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    -65.00  33.00   1.00    5.55    --  -40.80  38.00  30.00   98
  2  \w    -64.00  32.00   1.00    5.55    --  -40.80  57.00-120.00   96
  3  \w     48.00  80.00   1.00    5.55    --   40.80 -99.00   0.00   32
  4  \w     30.00  60.00   1.00    5.55    --   40.80-122.00 -56.00   30
  5  \w     91.00 133.00   1.00   22.20    --  107.14 -61.00  60.00   42
  6  \w     66.00 106.00   1.00   22.20    --  107.14 -95.00 -60.00   40
  7  \w     73.00 115.00   1.00   22.20    --  107.14-125.00-120.00   42
  8  \w     50.00 135.00   1.00   22.20    --  107.14 -61.00 -60.00   85
  9  \w    118.00 177.00   1.00   22.20    --  107.14   0.00-180.00   59
 10  \w    113.00 177.00   1.00   22.20    --  107.14  77.00 -90.00   64
 11  \w    131.00 177.00   1.00   22.20    --  107.14 125.00-120.00   46
 12  \w     82.00 177.00   1.00   22.20    --  107.14  45.00  30.00   95
 13  \w     79.00 128.00   1.00   22.20    --  107.14  61.00  90.00   49
 14  \w     57.00 105.00   1.00   22.20    --  107.14 -95.00  60.00   48
 15  \w     37.00  64.00   1.00   22.20    --  107.14-125.00-120.00   27
 16  \w     33.00 114.00   1.00   22.20    --  107.14 -77.00-150.00   81
 17  \w     37.00 127.00   1.00   22.20    --  107.14 -30.00-150.00   90
 18  \w     34.00  60.00   1.00   22.20    --  107.14   0.00-180.00   26
 19  \w   -108.00 -16.00   1.00    5.55    --  -40.80 -57.00  90.00   92
;
_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      0.0477738000
_diffrn_orient_matrix_UB_12      -0.0020581000
_diffrn_orient_matrix_UB_13      0.0935985000
_diffrn_orient_matrix_UB_21      -0.0139047000
_diffrn_orient_matrix_UB_22      -0.1142559000
_diffrn_orient_matrix_UB_23      -0.0265044000
_diffrn_orient_matrix_UB_31      0.1527303000
_diffrn_orient_matrix_UB_32      0.0116939000
_diffrn_orient_matrix_UB_33      -0.0103163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.657
_diffrn_reflns_theta_min         3.778
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.407
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67674
_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    1.161
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.967
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         8422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0655
_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^)+(0.1664P)^2^+0.0897P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2194
_refine_ls_wR_factor_ref         0.2324
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7084
_reflns_number_total             8422
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04885b2.cif
_cod_data_source_block           syy-20181109-a-882
_cod_depositor_comments
;
Adding full bibliography for 7127071--7127077.cif.

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C11.11 H7.11 N0.89 S0.44'
_cod_original_formula_weight         167.31
_cod_original_formula_moiety         '0.22(C50 H32 N4 S2)'
_cod_original_formula_units_Z            9
_cod_database_code               7127076
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_usercomment     'C H O N F'
_shelx_estimated_absorpt_t_max   0.729
_shelx_estimated_absorpt_t_min   0.711
_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
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38),
 C42(H42), C43(H43), C45(H45), C47(H47), C48(H48), C49(H49), C50(H50), C51(H51),
  C54(H54)
;
_platon_squeeze_void_probe_radius 1.20
_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 1.615
_oxdiff_exptl_absorpt_empirical_full_min 0.734