Four-Electron Oxidation of Phenols to p-Benzoquinone Imines by a (Salen)ruthenium(VI) Nitrido Complex.
Xie, Jianhui; Man, Wai-Lun; Wong, Chun-Yuen; Chang, Xiaoyong; Che, Chi-Ming; Lau, Tai-Chu; Journal of the American Chemical Society 138 (2016) 5817–5820; doi:10.1021/jacs.6b02923

data_4130399
_publ_section_title
;
 Four-Electron Oxidation of Phenols to p-Benzoquinone Imines by a
 (Salen)ruthenium(VI) Nitrido Complex.
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5817
_journal_page_last               5820
_journal_paper_doi               10.1021/jacs.6b02923
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety
'C31 H30 N4 O3 Ru, 2(C H2 Cl2), 0.5(C H4 O), 2(F3 P0.5)'
_chemical_formula_sum            'C33.5 H36 Cl4 F6 N4 O3.5 P Ru'
_chemical_formula_weight         938.50
_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
_audit_creation_date             2015-11-01
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.10.28 svn.r3245 for OlexSys, GUI svn.r5128)
;
_cell_angle_alpha                71.1540(10)
_cell_angle_beta                 82.2680(10)
_cell_angle_gamma                71.9180(10)
_cell_formula_units_Z            2
_cell_length_a                   12.1017(4)
_cell_length_b                   12.7507(4)
_cell_length_c                   14.0794(5)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.05
_cell_measurement_theta_min      3.82
_cell_volume                     1953.09(11)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6908
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.684
_diffrn_reflns_theta_min         3.319
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.771
_exptl_absorpt_correction_T_max  0.752878
_exptl_absorpt_correction_T_min  0.556146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0842 before and 0.0496 after correction.
 The Ratio of minimum to maximum transmission is 0.74.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 14245 reflections, Rint = 0.0307
 (11579 with I > 3sig(I), Rint = 0.0299)
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_description       block
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         2.057
_refine_diff_density_min         -2.171
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         6908
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0740
_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^)+(0.1139P)^2^+11.9926P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2049
_refine_ls_wR_factor_ref         0.2063
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6736
_reflns_number_total             6908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b02923_si_003.cif
_cod_data_source_block           twin4
_cod_original_cell_volume        1953.10(11)
_cod_original_formula_sum        'C33.50 H36 Cl4 F6 N4 O3.50 P Ru'
_cod_database_code               4130399
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.941(4) 0.059(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 O4-C34
 1.42 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uiso(O4) = Uiso(C34)
5. Others
 Fixed Sof: O4(0.5) H4A(0.5) C34(0.5) H34A(0.5) H34B(0.5) H34C(0.5)
6.a Ternary CH refined with riding coordinates:
 C8(H8), C13(H13)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C33(H33A,H33B),
 C32(H32A,H32B)
6.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), C7(H7), C14(H14), C16(H16), C17(H17),
  C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
 C27(H27), C28(H28), C30(H30), C31(H31)
6.d Tetrahedral OH refined with riding coordinates:
 O4(H4A)
6.e Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'