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_7128492
_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         'C39 H42 Cl N3 O Ru, C H2 Cl2, 0.5(C6 H14)'
_chemical_formula_sum            'C43 H51 Cl3 N3 O Ru'
_chemical_formula_weight         833.28
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-11
_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                87.2160(10)
_cell_angle_beta                 76.2490(10)
_cell_angle_gamma                88.1330(10)
_cell_formula_units_Z            8
_cell_length_a                   15.6278(2)
_cell_length_b                   19.7257(2)
_cell_length_c                   26.6898(2)
_cell_measurement_reflns_used    40234
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      75.6820
_cell_measurement_theta_min      2.8800
_cell_volume                     7980.52(15)
_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      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_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    -44.00 -19.00   0.50    0.05    --  -47.82   9.00  60.00   50
  2  \w    -63.00  17.00   0.50    0.05    --  -47.82  57.00  60.00  160
  3  \w    -61.00  -6.00   0.50    0.05    --  -47.82  57.00 -60.00  110
  4  \w    -60.00  25.00   0.50    0.05    --  -47.82  37.00-180.00  170
  5  \w     -4.00  45.00   0.50    0.05    --   47.82  -9.00-113.00   98
  6  \w     76.00 114.00   0.50    0.10    --  104.75  -9.00-113.00   76
  7  \w    148.00 174.00   0.50    0.10    --  104.75  45.00-180.00   52
  8  \w     84.00 125.00   0.50    0.10    --  104.75 -77.00 -90.00   82
  9  \w     58.00 108.00   0.50    0.10    --  104.75 -94.00-120.00  100
 10  \w     48.00  95.00   0.50    0.05    --   47.82-125.00-150.00   94
 11  \w     38.00  64.00   0.50    0.10    --  104.75 -77.00 -90.00   52
 12  \w     31.00 119.00   0.50    0.10    --  104.75 -15.00-150.00  176
 13  \w     59.00  96.00   0.50    0.10    --  104.75 -94.00   0.00   74
 14  \w     71.00 102.00   0.50    0.10    --  104.75 -94.00  60.00   62
 15  \w     78.00 108.00   0.50    0.10    --  104.75 -94.00  90.00   60
 16  \w     39.00  67.00   0.50    0.10    --  104.75 -94.00  60.00   56
 17  \w     33.00 117.00   0.50    0.10    --  104.75 -45.00 120.00  168
 18  \w    107.00 171.00   0.50    0.10    --  104.75   9.00  60.00  128
 19  \w     29.00 116.00   0.50    0.05    --   47.82   9.00  60.00  174
 20  \w     32.00 109.00   0.50    0.10    --  104.75 -94.00 -60.00  154
 21  \w     30.00 118.00   0.50    0.10    --  104.75 -30.00 -90.00  176
 22  \w     32.00 121.00   0.50    0.10    --  104.75 -61.00  30.00  178
 23  \w     32.00  90.00   0.50    0.10    --  104.75 -94.00 150.00  116
 24  \w   -118.00 -40.00   0.50    0.05    --  -47.82  -9.00-113.00  156
 25  \w   -113.00 -34.00   0.50    0.10    -- -102.00  45.00-180.00  158
 26  \w   -117.00 -75.00   0.50    0.10    -- -102.00 125.00-180.00   84
 27  \w   -112.00 -31.00   0.50    0.10    -- -102.00  61.00 -90.00  162
 28  \w    -97.00 -71.00   0.50    0.10    -- -102.00   9.00  60.00   52
 29  \w   -171.00 -90.00   0.50    0.10    -- -102.00  -9.00-113.00  162
;
_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      -0.0789382000
_diffrn_orient_matrix_UB_12      0.0503529000
_diffrn_orient_matrix_UB_13      0.0065797000
_diffrn_orient_matrix_UB_21      0.0628327000
_diffrn_orient_matrix_UB_22      0.0596407000
_diffrn_orient_matrix_UB_23      -0.0039559000
_diffrn_orient_matrix_UB_31      0.0111917000
_diffrn_orient_matrix_UB_32      0.0049342000
_diffrn_orient_matrix_UB_33      -0.0589793000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            96205
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.992
_diffrn_reflns_theta_min         2.243
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.307
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53918
_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            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             3464
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.195
_refine_diff_density_min         -2.739
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1924
_refine_ls_number_reflns         31941
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0797P)^2^+16.6954P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1688
_reflns_Friedel_coverage         0.000
_reflns_number_gt                23569
_reflns_number_total             31941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01871j2.cif
_cod_data_source_block           zb-zx
_cod_depositor_comments
'Adding full bibliography for 7128489--7128493.cif.'
_cod_database_code               7128492
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C1H1N1O1Cl1Ru1
_shelx_estimated_absorpt_t_max   0.417
_shelx_estimated_absorpt_t_min   0.299
_diffrn_oxdiff_digest_frames
;
016590161ce0ea2cc1f32ddada40587049000506b9d
;
_diffrn_oxdiff_digest_hkl
;
01b6c9f2fb492d8fae7bdb37195476cb674136
;
_reflns_odcompleteness_completeness 99.86
_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
 C1C, C154, C156, C76, C77, C78
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C1C \\sim C154 \\sim C156 \\sim C76 \\sim C77 \\sim C78: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Sof(C76A)=Sof(H76A)=Sof(C77A)=Sof(H77D)=Sof(H77E)=Sof(H77F)=Sof(C78A)=
 Sof(H78D)=Sof(H78E)=Sof(H78F)=1-FVAR(1)
 Sof(C76)=Sof(H76)=Sof(C77)=Sof(H77A)=Sof(H77B)=Sof(H77C)=Sof(C78)=Sof(H78A)=
 Sof(H78B)=Sof(H78C)=FVAR(1)
 Sof(C1A)=Sof(H1A)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C1C)=Sof(H1CA)=
 Sof(H1CB)=Sof(H1CC)=1-FVAR(2)
 Sof(C154)=Sof(H154)=Sof(C155)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C156)=
 Sof(H15D)=Sof(H15E)=Sof(H15F)=FVAR(2)
5.a Riding coordinates:
 C28(H28A,H28B,H28C)
5.b Ternary CH refined with riding coordinates:
 C37(H37), C1A(H1A), C154(H154), C76(H76), C76A(H76A), C115(H115)
5.c Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C142(H14A,H14B), C143(H14C,
 H14D), C144(H14E,H14F), C64(H64A,H64B), C65(H65A,H65B), C66(H66A,H66B),
 C103(H10A,H10B), C104(H10C,H10D), C105(H10E,H10F), C157(H15G,H15H), C158(H15I,
 H15J), C159(H15K,H15L), C160(H16V,H16W), C162(H16D,H16E), C163(H16F,H16G),
 C164(H16H,H16I), C165(H16J,H16K), C168(H16R,H16S), C169(H16T,H16U), C170(H17A,
 H17B), C171(H17C,H17D)
5.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C32(H32), C33(H33), C35(H35),
  C36(H36), C121(H121), C122(H122), C125(H125), C128(H128), C129(H129),
 C130(H130), C131(H131), C132(H132), C135(H135), C136(H136), C137(H137),
 C138(H138), C139(H139), C149(H149), C150(H150), C152(H152), C153(H153),
 C43(H43), C44(H44), C47(H47), C50(H50), C51(H51), C52(H52), C53(H53), C54(H54),
  C57(H57), C58(H58), C59(H59), C60(H60), C61(H61), C71(H71), C72(H72),
 C74(H74), C75(H75), C82(H82), C83(H83), C86(H86), C89(H89), C90(H90), C91(H91),
  C92(H92), C93(H93), C96(H96), C97(H97), C98(H98), C99(H99), C100(H100),
 C110(H110), C111(H111), C113(H113), C114(H114)
5.e Idealised Me refined as rotating group:
 C1(H1B,H1C,H1D), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C38(H38A,H38B,
 H38C), C39(H39A,H39B,H39C), C1B(H1BA,H1BB,H1BC), C1C(H1CA,H1CB,H1CC),
 C118(H11A,H11B,H11C), C145(H14G,H14H,H14I), C146(H14J,H14K,H14L), C147(H14M,
 H14N,H14O), C155(H15A,H15B,H15C), C156(H15D,H15E,H15F), C40(H40A,H40B,H40C),
 C67(H67A,H67B,H67C), C68(H68A,H68B,H68C), C69(H69A,H69B,H69C), C77(H77A,H77B,
 H77C), C77A(H77D,H77E,H77F), C78(H78A,H78B,H78C), C78A(H78D,H78E,H78F),
 C79(H79A,H79B,H79C), C106(H10G,H10H,H10I), C107(H10J,H10K,H10L), C108(H10M,
 H10N,H10O), C116(H11D,H11E,H11F), C117(H11G,H11H,H11I), C161(H16A,H16B,H16C),
 C166(H16L,H16M,H16N), C167(H16O,H16P,H16Q), C172(H17E,H17F,H17G)
;
_shelx_res_checksum              4885
_shelx_hkl_checksum              95443
_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 1.406
_oxdiff_exptl_absorpt_empirical_full_min 0.726