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_7128491
_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         'C33 H44 Cl N3 O4 Ru'
_chemical_formula_sum            'C33 H44 Cl N3 O4 Ru'
_chemical_formula_weight         683.23
_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             2019-11-29
_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                70.654(2)
_cell_angle_beta                 83.062(2)
_cell_angle_gamma                74.253(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2936(2)
_cell_length_b                   13.2026(3)
_cell_length_c                   15.1517(3)
_cell_measurement_reflns_used    13555
_cell_measurement_temperature    294.7(4)
_cell_measurement_theta_max      30.0680
_cell_measurement_theta_min      4.9210
_cell_volume                     1687.32(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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      air
_diffrn_ambient_temperature      294.7(4)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.872
_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    -29.00   1.00   0.50   56.77    --   -0.80 -37.00 -30.00   60
  2  \w    -88.00  17.00   0.50   56.77    --   -0.80 -77.00-180.00  210
  3  \w    -11.00  15.00   0.50   56.77    --   -0.80  37.00-180.00   52
  4  \w     37.00  86.00   0.50   56.77    --   -0.80  37.00-180.00   98
  5  \w    -16.00  68.00   0.50   56.77    --   -0.80  19.00  90.00  168
  6  \w    -21.00  83.00   0.50   56.77    --   -0.80  57.00 -90.00  208
  7  \w    -18.00  21.00   0.50   56.77    --   -0.80  37.00  60.00   78
  8  \w    -10.00  20.00   0.50   56.77    --   -0.80  37.00 150.00   60
  9  \w    -90.00 -40.00   0.50   56.77    --   -0.80 -37.00 -30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0120882000
_diffrn_orient_matrix_UB_12      0.0302685000
_diffrn_orient_matrix_UB_13      -0.0474152000
_diffrn_orient_matrix_UB_21      -0.0544048000
_diffrn_orient_matrix_UB_22      0.0469136000
_diffrn_orient_matrix_UB_23      0.0059064000
_diffrn_orient_matrix_UB_31      0.0564749000
_diffrn_orient_matrix_UB_32      0.0183219000
_diffrn_orient_matrix_UB_33      0.0134670000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33855
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.965
_diffrn_reflns_theta_min         4.815
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.582
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         8558
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+0.1562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0869
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7537
_reflns_number_total             8558
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01871j2.cif
_cod_data_source_block           zb-20191127
_cod_depositor_comments
'Adding full bibliography for 7128489--7128493.cif.'
_cod_database_code               7128491
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.897
_reflns_odcompleteness_completeness 99.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Restrained distances
 C18-C14 \\sim C17-C14 \\sim C16-C14 \\sim C15-C14 \\sim C20-C14 \\sim C19-C14
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C17)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: C15(0.65) H15A(0.65) H15B(0.65) H15C(0.65) C17(0.65) H17A(0.65)
 H17B(0.65) H17C(0.65) C19(0.65) H19A(0.65) H19B(0.65) H19C(0.65) C16(0.35)
 H16A(0.35) H16B(0.35) H16C(0.35) C20(0.35) H20A(0.35) H20B(0.35) H20C(0.35)
 C18(0.35) H18A(0.35) H18B(0.35) H18C(0.35)
5.a Ternary CH refined with riding coordinates:
 C33(H33)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
5.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C9(H9), C31(H31), C11(H11), C28(H28), C12(H12), C30(H30)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C26(H26A,H26B,H26C), C23(H23A,H23B,H23C), C34(H34A,H34B,
 H34C), C7(H7A,H7B,H7C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C15(H15A,
 H15B,H15C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C16(H16A,H16B,H16C),
 C20(H20A,H20B,H20C), C18(H18A,H18B,H18C)
;
_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 3.802
_oxdiff_exptl_absorpt_empirical_full_min 0.303