Planar chiral arene ruthenium complexes derived from <i>R</i>-carvone.
Boym, Mikhail A.; Pototskiy, Roman A.; Podyacheva, Evgeniya S.; Muratov, Dmitry V.; Nelyubina, Yulia V.; Perekalin, Dmitry S.; Dalton transactions (Cambridge, England : 2003) 54 (2025) 5655–5658; doi:10.1039/d5dt00344j

data_7718292
_publ_section_title
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 Planar chiral arene ruthenium complexes derived from <i>R</i>-carvone.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5655
_journal_page_last               5658
_journal_paper_doi               10.1039/d5dt00344j
_journal_volume                  54
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H32 Cl4 F12 Ru2'
_chemical_formula_sum            'C36 H32 Cl4 F12 Ru2'
_chemical_formula_weight         1036.55
_space_group_crystal_system      orthorhombic
_space_group_IT_number           23
_space_group_name_Hall           'I 2 2'
_space_group_name_H-M_alt        'I 2 2 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-18
_audit_creation_method
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Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-08-18 deposited with the CCDC.	2025-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.894(3)
_cell_length_b                   15.115(4)
_cell_length_c                   24.808(7)
_cell_measurement_reflns_used    1789
_cell_measurement_temperature    120
_cell_measurement_theta_max      3
_cell_measurement_theta_min      30
_cell_volume                     4085.0(19)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII Quazar CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1096
_diffrn_reflns_av_unetI/netI     0.1622
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9727
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.808
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.081
_exptl_absorpt_correction_T_max  0.1551
_exptl_absorpt_correction_T_min  0.0882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1666 before and 0.0669 after correction.
The Ratio of minimum to maximum transmission is 0.5687.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_description       plate
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.973
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.141
_refine_ls_abs_structure_details
;
 Flack x determined using 681 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3591
_refine_ls_number_restraints     257
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.0699
_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^)+(0.0529P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1509
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2133
_reflns_number_total             3591
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt00344j2.cif
_cod_data_source_block           4b
_cod_depositor_comments          'Adding full bibliography for 7718292.cif.'
_cod_original_cell_volume        4085(2)
_cod_database_code               7718292
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.813
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9'-C13 \\sim C9'-C13'
 with sigma of 0.02
 C7-C8 \\sim C7-C8'
 with sigma of 0.02
 F6'-C14 \\sim F6-C14
 with sigma of 0.02
 C8-C9' \\sim C8'-C9
 with sigma of 0.02
 C10'-C8 \\sim C20-C8'
 with sigma of 0.04
 C8-C13 \\sim C8'-C13
 with sigma of 0.04
 F1'-C9' \\sim F1-C9'
 with sigma of 0.04
 C8-C13' \\sim C8'-C13'
 with sigma of 0.04
 F3'-C9' \\sim F3-C9'
 with sigma of 0.04
 F2'-C9' \\sim F2-C9'
 with sigma of 0.04
 F4-C14 \\sim F4'-C14
 with sigma of 0.02
 C9-C8 \\sim C8'-C9'
 with sigma of 0.02
 C13'-C9' \\sim C13-C9'
 with sigma of 0.02
 F5-C14 \\sim F5'-C14
 with sigma of 0.02
 F2'-C13 \\sim F2-C13'
 with sigma of 0.02
 F1'-F3' \\sim F1-F3
 with sigma of 0.04
 C10'-C9' \\sim C20-C9
 with sigma of 0.02
 F1'-F2' \\sim F1-F2
 with sigma of 0.04
 F3'-F2' \\sim F3-F2
 with sigma of 0.04
 C9'-C13 \\sim C9-C13
 with sigma of 0.02
 C9'-C13' \\sim C9-C13'
 with sigma of 0.02
 C7-C9' \\sim C7-C9
 with sigma of 0.04
 C12-C10' \\sim C12-C20
 with sigma of 0.04
 F3'-C13 \\sim F3-C13'
 with sigma of 0.02
 F1'-C13 \\sim F1-C13'
 with sigma of 0.02
 C10'-C14 \\sim C20-C14
 with sigma of 0.04
 C10'-C13 \\sim C20-C13
 with sigma of 0.04
 C10'-C13' \\sim C20-C13'
 with sigma of 0.04
 C5-C16' \\sim C5-C16
 with sigma of 0.02
 C16'-C17' \\sim C16-C17
 with sigma of 0.02
 C16'-C18' \\sim C16-C18
 with sigma of 0.02
 C9-C10' \\sim C20-C9'
 with sigma of 0.02
 C5-C17' \\sim C5-C17
 with sigma of 0.04
 C13'-C9' \\sim C9-C13
 with sigma of 0.02
 C5-C18' \\sim C5-C18
 with sigma of 0.04
 C17'-C18' \\sim C17-C18
 with sigma of 0.04
 C16'-C5 \\sim C16-C5
 with sigma of 0.02
 C18'-C16' \\sim C16-C18
 with sigma of 0.02
 C17'-C16' \\sim C16-C17
 with sigma of 0.02
 Ru1-Cl3 \\sim Ru1-Cl3'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.006
Uanis(C4) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(C2) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(F1') \\sim Ueq, Uanis(F3') \\sim Ueq, Uanis(F2') \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C13') \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1) \\sim Ueq,
Uanis(F2) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(C16') \\sim Ueq, Uanis(C17') \\sim Ueq, Uanis(C18') \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of 0.003 and
sigma for terminal atoms of 0.006
Uanis(C11) \\sim Ueq, Uanis(C10') \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9')
\\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C8') \\sim Ueq, Uanis(C9) \\sim Ueq:
with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(F4) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6') \\sim Ueq: with sigma of
0.002 and sigma for terminal atoms of 0.004
Uanis(C5) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.006
Uanis(Cl3') \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C6) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(C15) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(Cl2) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(C14) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(F6') = Uanis(F6)
Uanis(F6) = Uanis(F6')
Uanis(C8') = Uanis(C8)
Uanis(F4') = Uanis(F4)
Uanis(F5) = Uanis(F5')
Uanis(F2) = Uanis(F2')
Uanis(F1') = Uanis(F1)
Uanis(F3') = Uanis(F3)
Uanis(C20) = Uanis(C10')
Uanis(C9) = Uanis(C9')
Uanis(C16) = Uanis(C16')
Uanis(C18) = Uanis(C18')
Uanis(C17') = Uanis(C17)
Uanis(Cl3') = Uanis(Cl3)
4. Rigid body (RIGU) restrains
 C11, C10', C8, C9'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C8', C9, C20
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F6)=Sof(C9)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(C8)=Sof(H8)=
 Sof(C13')=Sof(C20)=Sof(H20)=1-FVAR(1)
 Sof(F1')=Sof(F2')=Sof(F3')=Sof(F4')=Sof(F5')=Sof(C8')=Sof(H8')=Sof(C10')=
 Sof(H10')=Sof(C13)=Sof(F6')=Sof(C9')=FVAR(1)
 Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C18)=Sof(H18D)=
 Sof(H18E)=Sof(H18F)=1-FVAR(2)
 Sof(C16')=Sof(H16')=Sof(C17')=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C18')=
 Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(2)
 Sof(Cl3')=1-FVAR(3)
 Sof(Cl3)=FVAR(3)
 Fixed Sof: Cl2(0.5)
6.a Ternary CH refined with riding coordinates:
 C16'(H16'), C16(H16)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C12(H12), C8'(H8'), C10'(H10'), C8(H8), C20(H20)
6.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17'(H17A,H17B,H17C), C18'(H18A,H18B,H18C), C17(H17D,
 H17E,H17F), C18(H18D,H18E,H18F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              31234
_shelx_hkl_checksum              28937
_shelx_fab_checksum              81329
_olex2_submission_special_instructions 'No special instructions were received'