Vanadium(v) arylimido alkylidene N-heterocyclic carbene complexes containing fluorinated alkoxide or halogenated phenoxide ligands for the syndiospecific ROMP of cyclic olefins
Nomura, Kotohiro; Kuwahara, Shuko; Suthala, Jirapa; Kawamoto, Yuta; Shimoyama, Daisuke; Buchmeiser, Michael R.; New Journal of Chemistry 48 (2024) 14865–14872; doi:10.1039/D4NJ02537G

data_7063351
_publ_section_title
;
 Vanadium(v) arylimido alkylidene N-heterocyclic carbene complexes
 containing fluorinated alkoxide or halogenated phenoxide ligands for the
 syndiospecific ROMP of cyclic olefins
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14865
_journal_page_last               14872
_journal_paper_doi               10.1039/D4NJ02537G
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C33 H33 F11 N3 O Si V'
_chemical_formula_sum            'C33 H33 F11 N3 O Si V'
_chemical_formula_weight         775.65
_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             2024-05-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_audit_update_record
;
2024-05-25 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                91.240(2)
_cell_angle_beta                 95.293(3)
_cell_angle_gamma                111.900(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6615(4)
_cell_length_b                   12.4091(4)
_cell_length_c                   16.1836(5)
_cell_measurement_reflns_used    18611
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.9900
_cell_measurement_theta_min      2.3800
_cell_volume                     1789.27(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.851
_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    -98.00  82.00   0.50    5.00    --   -8.00   0.00-180.00  360
  2  \w    -98.00  82.00   0.50    5.00    --   -8.00  55.00-144.00  360
  3  \w    -98.00  82.00   0.50    5.00    --   -8.00  44.00  72.00  360
  4  \w    -98.00 -20.50   0.50    5.00    --   -8.00   0.00-144.00  155
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0385898000
_diffrn_orient_matrix_UB_12      -0.0609778000
_diffrn_orient_matrix_UB_13      0.0010375000
_diffrn_orient_matrix_UB_21      -0.0669738000
_diffrn_orient_matrix_UB_22      0.0086464000
_diffrn_orient_matrix_UB_23      0.0061064000
_diffrn_orient_matrix_UB_31      -0.0189793000
_diffrn_orient_matrix_UB_32      -0.0040221000
_diffrn_orient_matrix_UB_33      -0.0436602000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.851
_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       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26875
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_min         2.240
_diffrn_source
;
Advanced Light Source, station 11.3.1
;
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.186
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.041
_refine_diff_density_max         1.953
_refine_diff_density_min         -1.128
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     594
_refine_ls_number_reflns         8543
_refine_ls_number_restraints     529
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0790
_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^)+(0.1224P)^2^+4.7494P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2180
_refine_ls_wR_factor_ref         0.2238
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6382
_reflns_number_total             8543
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj02537g2.cif
_cod_data_source_block           20240114_f2nvcf3ixy
_cod_depositor_comments
'Adding full bibliography for 7063350--7063351.cif.'
_cod_original_cell_volume        1789.27(11)
_cod_database_code               7063351
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.930
_olex2_refinement_description
;
1. Shared sites
{C11B, Si1A}
{Si1B, C11A}
2. Restrained distances
 Si1B-C7B \\sim Si1A-C7A
 with sigma of 0.02
 F1B-C12B \\sim F4A-C13A
 with sigma of 0.02
 C11B-F1B \\sim C11A-F4A
 with sigma of 0.04
 F3B-C12B \\sim F6A-C13A
 with sigma of 0.02
 F3B-F1B \\sim F6A-F4A
 with sigma of 0.04
 F2B-F1B \\sim F5A-F4A
 with sigma of 0.04
 C11B-F3B \\sim C11A-F6A
 with sigma of 0.04
 F3B-F2B \\sim F6A-F5A
 with sigma of 0.04
 F8B-C14B \\sim F1A-C12A
 with sigma of 0.02
 F7B-C14B \\sim F3A-C12A
 with sigma of 0.02
 C11B-F8B \\sim C11A-F1A
 with sigma of 0.04
 C11B-F7B \\sim C11A-F3A
 with sigma of 0.04
 F9B-F8B \\sim F2A-F1A
 with sigma of 0.04
 F9B-F7B \\sim F2A-F3A
 with sigma of 0.04
 F8B-F7B \\sim F1A-F3A
 with sigma of 0.04
 Si1B-C8B \\sim Si1A-C10A
 with sigma of 0.02
 Si1B-C9B \\sim Si1A-C9A
 with sigma of 0.02
 C7B-C8B \\sim C7A-C10A
 with sigma of 0.04
 C7B-C9B \\sim C7A-C9A
 with sigma of 0.04
 F6B-C13B \\sim F7A-C14A
 with sigma of 0.02
 C8B-C9B \\sim C10A-C9A
 with sigma of 0.04
 C8B-C10B \\sim C10A-C8A
 with sigma of 0.04
 C9B-C10B \\sim C9A-C8A
 with sigma of 0.04
 Si1B-C10B \\sim Si1A-C8A
 with sigma of 0.02
 C11B-F6B \\sim C11A-F7A
 with sigma of 0.04
 C7B-C10B \\sim C7A-C8A
 with sigma of 0.04
 F5B-F6B \\sim F9A-F7A
 with sigma of 0.04
 F6B-F4B \\sim F7A-F8A
 with sigma of 0.04
 V1-C7B \\sim V1-C7A
 with sigma of 0.02
 V1-Si1B \\sim V1-Si1A
 with sigma of 0.04
 V1-O1B \\sim V1-O1A
 with sigma of 0.02
 O1B-C11B \\sim O1A-C11A
 with sigma of 0.02
 C11B-C13B \\sim C11A-C14A
 with sigma of 0.02
 C11B-C14B \\sim C11A-C12A
 with sigma of 0.02
 C11B-C12B \\sim C11A-C13A
 with sigma of 0.02
 F5B-C13B \\sim F9A-C14A
 with sigma of 0.02
 F9B-C14B \\sim F2A-C12A
 with sigma of 0.02
 F2B-C12B \\sim F5A-C13A
 with sigma of 0.02
 F4B-C13B \\sim F8A-C14A
 with sigma of 0.02
 V1-C11B \\sim V1-C11A
 with sigma of 0.04
 O1B-C13B \\sim O1A-C14A
 with sigma of 0.04
 O1B-C14B \\sim O1A-C12A
 with sigma of 0.04
 O1B-C12B \\sim O1A-C13A
 with sigma of 0.04
 C11B-F5B \\sim C11A-F9A
 with sigma of 0.04
 C11B-F9B \\sim C11A-F2A
 with sigma of 0.04
 C11B-F2B \\sim C11A-F5A
 with sigma of 0.04
 C11B-F4B \\sim C11A-F8A
 with sigma of 0.04
 F5B-F4B \\sim F9A-F8A
 with sigma of 0.04
 C13B-C14B \\sim C14A-C12A
 with sigma of 0.04
 C13B-C12B \\sim C14A-C13A
 with sigma of 0.04
 C14B-C12B \\sim C12A-C13A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
F7A \\sim F9A \\sim C13A \\sim F8A \\sim F5A \\sim F4A \\sim O1A \\sim C11A
\\sim F2A \\sim C12A \\sim F6A \\sim C14A \\sim F1A \\sim F3A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C14B \\sim C13B \\sim F8B \\sim F7B \\sim F9B \\sim F2B \\sim F1B \\sim C12B
\\sim F3B \\sim O1B \\sim F4B \\sim F5B \\sim F6B \\sim C11B \\sim V1: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C9A \\sim C10A \\sim C7A \\sim Si1A \\sim C8A \\sim V1: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.01 within 2A
Uanis(C10A) \\sim Ueq, Uanis(C9A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C8A) = Uanis(Si1A) = Uanis(C10A) = Uanis(C9A)
Uanis(C11B) = Uanis(Si1A)
Uanis(Si1B) = Uanis(C11A)
4. Rigid body (RIGU) restrains
 C14B, F5B, F8B, F7B, F9B, F2B, C11B, F3B, O1B, F4B, C13B, C12B, F6B, F1B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F7A, F1A, C13A, F8A, F5A, F4A, C14A, F2A, O1A, F6A, F9A, C11A, F3A, C12A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C7A, Si1A, C10A, C9A, C8A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 V1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7B, Si1B, C10B, C8B, C9B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C7A)=Sof(H7A)=Sof(Si1A)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=Sof(C9A)=
 Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=
 Sof(C12A)=Sof(C14A)=Sof(F1A)=Sof(F3A)=Sof(F2A)=Sof(F5A)=Sof(F4A)=Sof(C13A)=
 Sof(F6A)=Sof(O1A)=Sof(F8A)=Sof(F9A)=Sof(F7A)=Sof(C11A)=1-FVAR(1)
 Sof(Si1B)=Sof(O1B)=Sof(C7B)=Sof(H7B)=Sof(C11B)=Sof(C8B)=Sof(H8BA)=Sof(H8BB)=
 Sof(H8BC)=Sof(C9B)=Sof(H9BA)=Sof(H9BB)=Sof(H9BC)=Sof(C10B)=Sof(H10A)=Sof(H10B)=
 Sof(H10C)=Sof(F5B)=Sof(F6B)=Sof(F3B)=Sof(F9B)=Sof(F2B)=Sof(F8B)=Sof(F4B)=
 Sof(F1B)=Sof(F7B)=Sof(C13B)=Sof(C14B)=Sof(C12B)=FVAR(1)
6.a Me refined with riding coordinates:
 C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC), C10A(H10D,H10E,H10F)
6.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C5(H5), C4(H4), C16(H16), C30(H30), C29(H29), C28(H28), C3(H3),
 C22(H22), C20(H20), C21(H21), C7B(H7B), C7A(H7A)
6.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C33(H33A,H33B,H33C), C32(H32A,H32B,
 H32C), C8B(H8BA,H8BB,H8BC), C9B(H9BA,H9BB,H9BC), C10B(H10A,H10B,H10C)
;
_shelx_res_checksum              55701
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.482
_oxdiff_exptl_absorpt_empirical_full_min 0.720