Enolate SNAr of unactivated arenes via [(η6-arene)RuCp]+ intermediates
Williams, Luke J.; Bhonoah, Yunas; Walton, James W.; Chemical Communications  (2022) –; doi:10.1039/D2CC02508F

data_7130272
_publ_section_title
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 Enolate SNAr of unactivated arenes via [(\h6-arene)RuCp]+ intermediates
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02508F
_journal_year                    2022
_chemical_formula_moiety         'C13 H14 N O2 Ru, F6 P'
_chemical_formula_sum            'C13 H14 F6 N O2 P Ru'
_chemical_formula_weight         462.29
_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     direct
_audit_creation_date             2021-02-10
_audit_creation_method
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_audit_update_record
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2022-05-03 deposited with the CCDC.	2022-06-17 downloaded from the CCDC.
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_cell_angle_alpha                90
_cell_angle_beta                 112.2030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.7069(7)
_cell_length_b                   14.2729(6)
_cell_length_c                   14.1391(6)
_cell_measurement_reflns_used    9521
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.52
_cell_measurement_theta_min      2.78
_cell_volume                     3121.6(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS, 2016)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS, 2016)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON III C7 MM CPAD'
_diffrn_detector_area_resol_mean 54.8
_diffrn_detector_type            'CPA sensor'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w- and \f-scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            52996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         1.941
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.179
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0554 before and 0.0404 after correction.
The Ratio of minimum to maximum transmission is 0.9215.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.967
_exptl_crystal_description       prism
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.849
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         9078
_refine_ls_number_restraints     67
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0230P)^2^+3.5520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0572
_refine_ls_wR_factor_ref         0.0593
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8198
_reflns_number_total             9078
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02508f2.cif
_cod_data_source_block           3c_21srv062
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7130272
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.843
_shelx_estimated_absorpt_t_min   0.773
_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
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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
 O1AA-N1A \\sim O1A-N1A
 with sigma of 0.002
 P1-F2A \\sim P1-F2 \\sim P1-F5 \\sim P1-F1A \\sim P1-F1 \\sim P1-F4 \\sim
P1-F3A \\sim P1-F3 \\sim P1-F5A ~
 P1-F6 \\sim P1-F6A \\sim P1-F4A
 with sigma of 0.002
3. Others
 Fixed Sof: O1A(0.7) O1AA(0.3) F1(0.9) F1A(0.1) F2(0.9) F2A(0.1) F3(0.9)
 F3A(0.1) F4(0.9) F4A(0.1) F5(0.9) F5A(0.1) F6(0.9) F6A(0.1)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C3A(H3A), C4A(H4A), C5A(H5A), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A),
 C13A(H13A)
4.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C7A(H7AA,H7AB,H7AC), C8A(H8AA,H8AB,H8AC)
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_olex2_submission_special_instructions 'No special instructions were received'