Preparation of pyridyltriazole ruthenium complexes as effective catalysts for the selective alkylation and one-pot C‒H hydroxylation of 2-oxindole with alcohols and mechanism exploration
Wu, Qiang; Pan, Le; Du, Guangming; Zhang, Chi; Wang, Dawei; Organic Chemistry Frontiers 5 (2018) 2668–; doi:10.1039/C8QO00725J

data_1554393
_publ_section_title
;
 Preparation of pyridyltriazole ruthenium complexes as effective catalysts
 for the selective alkylation and one-pot C--H hydroxylation of 2-oxindole
 with alcohols and mechanism exploration
;
_journal_issue                   18
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2668
_journal_paper_doi               10.1039/C8QO00725J
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C21 H22 Cl N4 Ru, F6 P, C H2 Cl2'
_chemical_formula_sum            'C22 H24 Cl3 F6 N4 P Ru'
_chemical_formula_weight         696.84
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-22
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2018-06-04 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.159(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1716(4)
_cell_length_b                   30.1115(13)
_cell_length_c                   10.9853(5)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.410
_cell_measurement_theta_min      3.058
_cell_volume                     2692.1(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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_temperature      100
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30775
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_min         2.982
_exptl_absorpt_coefficient_mu    1.001
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0624 before and 0.0476 after correction.
The Ratio of minimum to maximum transmission is 0.8936.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_refine_diff_density_max         1.247
_refine_diff_density_min         -1.152
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.266
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         5494
_refine_ls_number_restraints     198
_refine_ls_restrained_S_all      1.304
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0123P)^2^+11.7502P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5165
_reflns_number_total             5494
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00725j2.cif
_cod_data_source_block           mo_ybb1_0m
_cod_database_code               1554393
_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. Uiso/Uaniso restraints and constraints
Uanis(F6) \\sim Ueq, Uanis(F5A) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1A)
\\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F4A) \\sim Ueq, Uanis(F6A) \\sim Ueq,
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F5) \\sim
Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of
0.01
3. Rigid body (RIGU) restrains
 P1, F1, F2, F3, F4, F5, F6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 P1, F1, F1A, F2, F2A, F3, F3A, F4, F4A, F5, F5A, F6, F6A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C19(H19)
5.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C16(H16), C17(H17)
5.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              54241
_shelx_hkl_checksum              49424
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'