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_7127077
_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         'C56 H37 F3 N4'
_chemical_formula_sum            'C56 H37 F3 N4'
_chemical_formula_weight         822.94
_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                 90.879(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7038(3)
_cell_length_b                   10.8165(2)
_cell_length_c                   28.0637(6)
_cell_measurement_reflns_used    7147
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      72.1260
_cell_measurement_theta_min      4.9400
_cell_volume                     4766.34(16)
_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 (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 0.998
_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  21.00   1.00    6.13    --  -40.92  38.00  30.00   86
  2  \w   -110.00 -17.00   1.00    6.13    --  -40.92 -38.00  30.00   93
  3  \w     64.00  91.00   1.00    6.13    --   40.92-125.00   0.00   27
  4  \w     25.00 155.00   1.00   24.50    --  105.27 -15.00 -90.00  130
  5  \w     28.00 109.00   1.00   24.50    --  105.27 -95.00-180.00   81
  6  \w    112.00 168.00   1.00   24.50    --  105.27  45.00  90.00   56
  7  \w     63.00  98.00   1.00   24.50    --  105.27 -95.00 120.00   35
  8  \w     32.00 111.00   1.00   24.50    --  105.27 -45.00  30.00   79
  9  \w     80.00 108.00   1.00   24.50    --  105.27 -45.00 -60.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0734201000
_diffrn_orient_matrix_UB_12      0.0042417000
_diffrn_orient_matrix_UB_13      0.0369901000
_diffrn_orient_matrix_UB_21      -0.0642977000
_diffrn_orient_matrix_UB_22      -0.0172649000
_diffrn_orient_matrix_UB_23      0.0403931000
_diffrn_orient_matrix_UB_31      0.0101582000
_diffrn_orient_matrix_UB_32      -0.1412874000
_diffrn_orient_matrix_UB_33      -0.0038436000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17167
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.764
_diffrn_reflns_theta_min         4.381
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65418
_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            colorless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_description       prism
_exptl_crystal_F_000             1737
_refine_diff_density_max         0.886
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.260
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         9199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.260
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0902
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2846
_refine_ls_wR_factor_ref         0.3053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7307
_reflns_number_total             9199
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04885b2.cif
_cod_data_source_block           syy-a-937-1
_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            'C10.67 H7.05 Cl0.05 F0.57 N0.76 O0.05'
_cod_original_formula_weight         159.19
_cod_original_formula_moiety         '0.19(C56 H37 F3 N4)'
_cod_original_formula_units_Z            21
_cod_database_code               7127077
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_usercomment     'C H N'
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C28(H28),
  C30(H30), C31(H31), C32(H32), C33(H33), C34(H34), C40(H40), C41(H41),
 C43(H43), C45(H45), C46(H46), C47(H47), C48(H48), C49(H49), C51(H51), C52(H52),
  C53(H53), C54(H54), C55(H55)
2.b Idealised Me refined as rotating group:
 C0AA(H0AA,H0AB,H0AC)
;
_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 1.445
_oxdiff_exptl_absorpt_empirical_full_min 0.409