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_7127072
_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         'C54 H34 Cl2 N4'
_chemical_formula_sum            'C54 H34 Cl2 N4'
_chemical_formula_weight         809.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 96.853(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.3538(10)
_cell_length_b                   10.7542(10)
_cell_length_c                   15.7395(12)
_cell_measurement_reflns_used    3199
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.3150
_cell_measurement_theta_min      4.5670
_cell_volume                     2244.2(3)
_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 0.990
_diffrn_measured_fraction_theta_max 0.958
_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     30.00  57.00   1.00    4.56    --   40.80 -38.00 -90.00   27
  2  \w     56.00  83.00   1.00    4.56    --   40.80-125.00 -60.00   27
  3  \w     33.00 105.00   1.00   18.23    --  107.14 -95.00 -90.00   72
  4  \w     37.00 132.00   1.00   18.23    --  107.14 -45.00 -60.00   95
  5  \w     84.00 174.00   1.00   18.23    --  107.14  30.00 120.00   90
  6  \w    109.00 135.00   1.00   18.23    --  107.14 125.00 120.00   26
  7  \w    152.00 177.00   1.00   18.23    --  107.14 125.00 120.00   25
  8  \w     94.00 124.00   1.00   18.23    --  107.14 125.00 -60.00   30
  9  \w    117.00 154.00   1.00   18.23    --  107.14 125.00-120.00   37
 10  \w     26.00  97.00   1.00   18.23    --  107.14 -95.00-150.00   71
 11  \w    -63.00   6.00   1.00    4.56    --  -40.80  38.00  90.00   69
 12  \w    -68.00  31.00   1.00    4.56    --  -40.80  57.00 150.00   99
;
_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      -0.1074773000
_diffrn_orient_matrix_UB_12      0.0454462000
_diffrn_orient_matrix_UB_13      0.0097507000
_diffrn_orient_matrix_UB_21      0.0377649000
_diffrn_orient_matrix_UB_22      0.1354465000
_diffrn_orient_matrix_UB_23      0.0045801000
_diffrn_orient_matrix_UB_31      -0.0229523000
_diffrn_orient_matrix_UB_32      0.0111067000
_diffrn_orient_matrix_UB_33      -0.0979388000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8853
_diffrn_reflns_point_group_measured_fraction_full 0.744
_diffrn_reflns_point_group_measured_fraction_max 0.709
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.884
_diffrn_reflns_theta_min         4.624
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35208
_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    1.200
_exptl_crystal_description       prism
_exptl_crystal_F_000             842
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         6457
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0836
_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^)+(0.1625P)^2^+0.0749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2270
_refine_ls_wR_factor_ref         0.2423
_reflns_Friedel_coverage         0.401
_reflns_Friedel_fraction_full    0.468
_reflns_Friedel_fraction_max     0.430
_reflns_number_gt                5538
_reflns_number_total             6457
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04885b2.cif
_cod_data_source_block           syy-a-869-tm
_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_weight         162.15
_cod_original_formula_moiety         '0.2(C54 H34 Cl2 N4)'
_cod_original_formula_units_Z            10
_cod_original_formula_sum        'C10.80 H7 Cl0.40 N0.80'
_cod_database_code               7127072
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_usercomment     'C H O N'
_shelx_estimated_absorpt_t_max   0.699
_shelx_estimated_absorpt_t_min   0.680
_reflns_odcompleteness_completeness 98.99
_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:
 C2(H2), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C30(H30), C31(H31), C32(H32), C33(H33), C34(H34), C36(H36), C37(H37),
 C39(H39), C44(H44), C45(H45), C46(H46), C47(H47), C48(H48), C49(H49), C50(H50),
  C51(H51), C52(H52), C53(H53)
;
_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 3.950
_oxdiff_exptl_absorpt_empirical_full_min 0.358