Planar-chiral arene ruthenium complexes: synthesis, separation of enantiomers, and application for catalytic C-H activation.
Boym, Mikhail A.; Pototskiy, Roman A.; Podyacheva, Evgeniya S.; Chusov, Denis A.; Nelyubina, Yulia V.; Perekalin, Dmitry S.; Chemical communications (Cambridge, England) 60 (2024) 4491–4494; doi:10.1039/d4cc00181h

data_7132895
_publ_section_title
;
 Planar-chiral arene ruthenium complexes: synthesis, separation of
 enantiomers, and application for catalytic C-H activation.
;
_journal_issue                   33
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4491
_journal_page_last               4494
_journal_paper_doi               10.1039/d4cc00181h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C14 H20 Cl3 Ru, C14 H20 Ru, Cl'
_chemical_formula_sum            'C28 H40 Cl4 Ru2'
_chemical_formula_weight         720.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-08
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2024-01-08 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.047(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2863(4)
_cell_length_b                   18.7694(5)
_cell_length_c                   12.3374(3)
_cell_measurement_reflns_used    8585
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.52
_cell_volume                     2841.06(14)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30298
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         1.660
_exptl_absorpt_coefficient_mu    1.456
_exptl_absorpt_correction_T_max  0.1561
_exptl_absorpt_correction_T_min  0.0969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1364 before and 0.0671 after correction.
The Ratio of minimum to maximum transmission is 0.6208.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_description       prism
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.165
_refine_diff_density_min         -0.942
_refine_diff_density_rms         0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         6200
_refine_ls_number_restraints     86
_refine_ls_restrained_S_all      1.182
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0766
_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^)+(0.0192P)^2^+33.7994P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1690
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4856
_reflns_number_total             6200
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00181h3.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7132893--7132895.cif.'
_cod_database_code               7132895
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.868
_shelx_estimated_absorpt_t_min   0.811
_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
 C27'-C25' \\sim C27-C25
 with sigma of 0.02
 C24-C15 \\sim C21'-C20'
 with sigma of 0.02
 C23-C24 \\sim C21'-C22'
 with sigma of 0.02
 C24'-C23' \\sim C21-C22
 with sigma of 0.02
 C21-C20 \\sim C15'-C24'
 with sigma of 0.02
 C23-C22 \\sim C23'-C22'
 with sigma of 0.02
 C25'-C26' \\sim C25-C28
 with sigma of 0.02
 C25-C26 \\sim C25'-C28'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C26) \\sim Ueq, Uanis(C23') \\sim Ueq, Uanis(C22') \\sim Ueq, Uanis(C21')
\\sim Ueq, Uanis(C24') \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C27) \\sim Ueq:
with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C19') \\sim Ueq, Uanis(C18') \\sim Ueq, Uanis(C17') \\sim Ueq,
Uanis(C16') \\sim Ueq, Uanis(C15') \\sim Ueq, Uanis(C20') \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(C27') = Uanis(C27)
Uanis(Ru1') = Uanis(Ru1)
Uanis(Cl3') = Uanis(Cl3)
Uanis(C25') = Uanis(C25)
Uanis(C26) = Uanis(C28')
Uanis(C28) = Uanis(C26')
Uanis(C24) = Uanis(C21')
Uanis(C17') = Uanis(C15)
Uanis(C15') = Uanis(C19)
Uanis(C20') = Uanis(C18)
Uanis(C19') = Uanis(C17)
Uanis(C16') = Uanis(C20)
Uanis(C24') = Uanis(C21)
Uanis(C18') = Uanis(C16)
Uanis(C22) = Uanis(C23')
Uanis(C22') = Uanis(C23)
4. Others
 Sof(Ru1')=Sof(Cl3')=Sof(H5B)=1-FVAR(1)
 Sof(Ru1)=Sof(Cl3)=Sof(H5A)=FVAR(1)
 Sof(C20')=Sof(C15')=Sof(C16')=Sof(H16')=Sof(C17')=Sof(C18')=Sof(H18')=
 Sof(C19')=Sof(H19')=Sof(C21')=Sof(H21C)=Sof(H21D)=Sof(C22')=Sof(H22C)=
 Sof(H22D)=Sof(C23')=Sof(H23C)=Sof(H23D)=Sof(C24')=Sof(H24C)=Sof(H24D)=
 Sof(C25')=Sof(C26')=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C27')=Sof(H27D)=
 Sof(H27E)=Sof(H27F)=Sof(C28')=Sof(H28A)=Sof(H28B)=Sof(H28C)=1-FVAR(2)
 Sof(C19)=Sof(H19)=Sof(C20)=Sof(C15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=
 Sof(C18)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=
 Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(C26)=Sof(H26D)=
 Sof(H26E)=Sof(H26F)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=Sof(C28)=Sof(H28D)=
 Sof(H28E)=Sof(H28F)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C5(H5B), C5(H5A), C18'(H18'), C19'(H19')
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C21(H21A,H21B),
 C21'(H21C,H21D), C22(H22A,H22B), C22'(H22C,H22D), C23(H23A,H23B), C23'(H23C,
 H23D), C24(H24A,H24B), C24'(H24C,H24D)
5.c Me refined with riding coordinates:
 C27'(H27D,H27E,H27F)
5.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C19(H19), C16(H16), C17(H17), C16'(H16')
5.e Fitted hexagon refined as free rotating group:
 C19(C20,C15,C16,C17,C18), C20'(C15',C16',C17',C18',C19')
5.f Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C26'(H26A,H26B,
 H26C), C26(H26D,H26E,H26F), C27(H27A,H27B,H27C), C28'(H28A,H28B,H28C),
 C28(H28D,H28E,H28F)
;
_shelx_res_checksum              98006
_shelx_hkl_checksum              4028
_olex2_submission_special_instructions 'No special instructions were received'