Uncommon carbene-to-azole ligand rearrangement of N-heterocyclic carbenes in a ruthenium system.
Zhang, Bo; Duan, Yu'ai; Zhang, Xin; Guo, Shuai; Chemical communications (Cambridge, England) 57 (2021) 6879–6882; doi:10.1039/d1cc01871j

data_7128490
_publ_section_title
;
 Uncommon carbene-to-azole ligand rearrangement of N-heterocyclic carbenes
 in a ruthenium system.
;
_journal_issue                   56
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6879
_journal_page_last               6882
_journal_paper_doi               10.1039/d1cc01871j
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C41 H48 Cl N3 Ru'
_chemical_formula_sum            'C41 H48 Cl N3 Ru'
_chemical_formula_weight         719.34
_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             2019-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-02 deposited with the CCDC.	2021-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                66.9240(10)
_cell_angle_beta                 77.554(2)
_cell_angle_gamma                79.5920(10)
_cell_formula_units_Z            2
_cell_length_a                   9.7938(2)
_cell_length_b                   13.4269(2)
_cell_length_c                   14.9677(2)
_cell_measurement_reflns_used    17561
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.4440
_cell_measurement_theta_min      3.5860
_cell_volume                     1758.05(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.962
_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    -14.00  18.00   0.50    0.05    --   47.70 -73.00   9.00   64
  2  \w     30.00  61.00   0.50    0.05    --   47.70 -73.00   9.00   62
  3  \w     21.00  95.00   0.50    0.05    --   47.70-125.00  30.00  148
  4  \w     85.00 116.00   0.50    0.05    --  104.75-125.00 -30.00   62
  5  \w     69.00  95.00   0.50    0.05    --   47.70-125.00-180.00   52
  6  \w     83.00 108.00   0.50    0.05    --  104.75 -94.00-180.00   50
  7  \w     32.00  73.00   0.50    0.05    --  104.75-125.00 -30.00   82
  8  \w     32.00  75.00   0.50    0.05    --  104.75 -73.00   9.00   86
  9  \w     32.00 109.00   0.50    0.05    --  104.75 -94.00 -30.00  154
 10  \w     32.00 108.00   0.50    0.05    --  104.75 -94.00-150.00  152
 11  \w     18.00  53.00   0.50    0.05    --   47.70-125.00-180.00   70
 12  \w     92.00 172.00   0.50    0.05    --  104.75  30.00-120.00  160
 13  \w    106.00 178.00   0.50    0.05    --  104.75  30.00-150.00  144
 14  \w     94.00 131.00   0.50    0.05    --  104.75  45.00 -60.00   74
 15  \w    104.00 167.00   0.50    0.05    --  104.75  45.00  90.00  126
 16  \w    121.00 147.00   0.50    0.05    --  104.75  73.00 139.00   52
 17  \w     93.00 178.00   0.50    0.05    --  104.75  30.00 150.00  170
 18  \w     88.00 114.00   0.50    0.05    --   47.70  73.00 139.00   52
 19  \w     87.00 114.00   0.50    0.05    --  104.75  73.00 139.00   54
 20  \w     27.00  82.00   0.50    0.05    --   47.70  73.00 139.00  110
 21  \w     33.00 108.00   0.50    0.05    --  104.75 -94.00 120.00  150
 22  \w    -69.00  15.00   0.50    0.05    --  -47.70  73.00 139.00  168
 23  \w    -73.00 -41.00   0.50    0.05    -- -102.00  61.00 -30.00   64
 24  \w    -55.00 -30.00   0.50    0.05    -- -102.00  45.00 -60.00   50
 25  \w   -111.00 -27.00   0.50    0.05    --  -47.70 -73.00   9.00  168
 26  \w   -112.00 -82.00   0.50    0.05    --  -47.70-125.00 120.00   60
 27  \w   -118.00 -71.00   0.50    0.05    --  -47.70-125.00  90.00   94
 28  \w   -156.00 -92.00   0.50    0.05    -- -102.00 -73.00   9.00  128
 29  \w   -103.00 -31.00   0.50    0.05    -- -102.00  45.00 120.00  144
 30  \w    -98.00 -68.00   0.50    0.05    -- -102.00  73.00 139.00   60
 31  \w   -115.00 -29.00   0.50    0.05    -- -102.00  77.00  90.00  172
 32  \w   -117.00 -31.00   0.50    0.05    -- -102.00 125.00 120.00  172
 33  \w   -116.00 -82.00   0.50    0.05    -- -102.00  61.00 -30.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1564241000
_diffrn_orient_matrix_UB_12      0.0191222000
_diffrn_orient_matrix_UB_13      -0.0245948000
_diffrn_orient_matrix_UB_21      -0.0312412000
_diffrn_orient_matrix_UB_22      0.1037283000
_diffrn_orient_matrix_UB_23      -0.0889249000
_diffrn_orient_matrix_UB_31      -0.0283735000
_diffrn_orient_matrix_UB_32      0.0678919000
_diffrn_orient_matrix_UB_33      0.0658223000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22078
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.685
_diffrn_reflns_theta_min         3.251
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.937
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         7036
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+1.5168P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0768
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6684
_reflns_number_total             7036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01871j2.cif
_cod_data_source_block           zb-zx-2
_cod_depositor_comments
'Adding full bibliography for 7128489--7128493.cif.'
_cod_database_code               7128490
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c1h1n1Cl1Ru1
_shelx_estimated_absorpt_t_max   0.659
_shelx_estimated_absorpt_t_min   0.549
_diffrn_oxdiff_digest_frames
;
01ee305079addfb3fc9e6f21f5b08d1078000649699
;
_diffrn_oxdiff_digest_hkl
;
01e47a0bc207b82be526901055fce13787f90f
;
_reflns_odcompleteness_completeness 99.94
_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. Rigid bond restraints
 C39A, C39B, C40A, C40B, C41A, C41B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C39A \\sim C39B \\sim C40A \\sim C40B \\sim C41A \\sim C41B: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C39A) \\sim Ueq, Uanis(C39B) \\sim Ueq, Uanis(C40A) \\sim Ueq,
Uanis(C40B) \\sim Ueq, Uanis(C41A) \\sim Ueq, Uanis(C41B) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Sof(C39A)=Sof(H39A)=Sof(H39B)=Sof(H39C)=Sof(C40A)=Sof(H40A)=Sof(H40B)=
 Sof(H40C)=Sof(C41A)=Sof(H41A)=Sof(H41B)=Sof(H41C)=1-FVAR(1)
 Sof(C39B)=Sof(H39D)=Sof(H39E)=Sof(H39F)=Sof(C40B)=Sof(H40D)=Sof(H40E)=
 Sof(H40F)=Sof(C41B)=Sof(H41D)=Sof(H41E)=Sof(H41F)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C34(H34), C36(H36),
  C37(H37)
5.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C16(H16A,H16B,H16C),
 C17(H17A,H17B,H17C), C39A(H39A,H39B,H39C), C39B(H39D,H39E,H39F), C40A(H40A,
 H40B,H40C), C40B(H40D,H40E,H40F), C41A(H41A,H41B,H41C), C41B(H41D,H41E,H41F)
;
_shelx_res_checksum              46523
_shelx_hkl_checksum              4867
_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 1.443
_oxdiff_exptl_absorpt_empirical_full_min 0.782