Monomeric Octahedral Ruthenium(II) Complex Enabled meta-C‒H Nitration of Arenes with Removable Auxiliaries
Fan, Zhoulong; Li, Jie; Lu, Heng; Wang, Dong-Yu; Wang, Chao; Uchiyama, Masanobu; Zhang, Ao; Organic Letters  (2017) –; doi:10.1021/acs.orglett.7b01297

data_1546193
_publ_section_title
;
 Monomeric Octahedral Ruthenium(II) Complex Enabled meta-C--H Nitration of
 Arenes with Removable Auxiliaries
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.7b01297
_journal_year                    2017
_chemical_formula_moiety         'C13 H12 F3 N O6 Ru'
_chemical_formula_sum            'C13 H12 F3 N O6 Ru'
_chemical_formula_weight         436.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2016-12-29
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.12.12 svn.r3370 for OlexSys, GUI svn.r5282)
;
_cell_angle_alpha                89.047(8)
_cell_angle_beta                 68.729(7)
_cell_angle_gamma                70.014(8)
_cell_formula_units_Z            2
_cell_length_a                   8.558(4)
_cell_length_b                   9.278(4)
_cell_length_c                   11.548(5)
_cell_measurement_reflns_used    2508
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.68
_cell_volume                     796.9(6)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      170
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II 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  0.0195
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6000
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.997
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         1.907
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.046
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0529 before and 0.0260 after correction. The Ratio of minimum to maximum transmission is 0.7963. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.818
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.885
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0746P)^2^+0.2312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0916
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2939
_reflns_number_total             3073
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01297_si_002.cif
_cod_data_source_block           mo_2016911_0m
_cod_database_code               1546193
_shelx_shelxl_version_number     2014/7
_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, All O(H,H) groups
2.a Rotating group:
 O6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'