Combination of RuCl3·xH2O with PEG – a simple and recyclable catalytic system for direct arylation of heteroarenes via C–H bond activation
Jian, Lei; He, Hai-Yu; Huang, Jin; Wu, Qian-Hui; Yuan, Mao-Lin; Fu, Hai-Yan; Zheng, Xue-Li; Chen, Hua; Li, Rui-Xiang; RSC Adv. 7 (2017) 23515–; doi:10.1039/C7RA02638B

data_7228160
_publ_section_title
;
 Combination of RuCl3&#x00B7;xH2O with PEG -- a simple and recyclable
 catalytic system for direct arylation of heteroarenes via C--H bond
 activation
;
_journal_issue                   38
_journal_name_full               'RSC Adv.'
_journal_page_first              23515
_journal_paper_doi               10.1039/C7RA02638B
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C25 H15 F6 N'
_chemical_formula_sum            'C25 H15 F6 N'
_chemical_formula_weight         443.38
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-05-25 deposited with the CCDC.
2017-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.493(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6865(3)
_cell_length_b                   11.0532(4)
_cell_length_c                   22.5491(8)
_cell_measurement_reflns_used    3845
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2810
_cell_measurement_theta_min      3.9130
_cell_volume                     2155.08(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    4.8800
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000   30.0000 74

  2 omega    1.00   75.00   1.0000    4.8800
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000 -180.0000 74

  3 omega   23.00   90.00   1.0000    4.8800
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000    0.0000 67

  4 omega  -31.00   63.00   1.0000    4.8800
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000  120.0000 94

  5 omega  -33.00   55.00   1.0000    4.8800
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -38.0000  -60.0000 88

  6 omega   18.00  106.00   1.0000    4.8800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   38.0000  120.0000 88

  7 omega   38.00   91.00   1.0000   19.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

  8 omega   40.00   98.00   1.0000   19.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

  9 omega   38.00   91.00   1.0000   19.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 10 omega   91.00  176.00   1.0000   19.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 85

 11 omega   91.00  176.00   1.0000   19.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 85

 12 omega   40.00   98.00   1.0000   19.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 13 omega   40.00   98.00   1.0000   19.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

 14 omega   38.00   91.00   1.0000   19.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 15 omega   81.00  176.00   1.0000   19.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 95

 16 omega   20.00  104.00   1.0000    4.8800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000    0.0000 84

 17 omega   20.00   57.00   1.0000    4.8800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000 -180.0000 37

 18 omega   10.00  104.00   1.0000    4.8800
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000 -120.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1757881000
_diffrn_orient_matrix_UB_12      -0.0121940000
_diffrn_orient_matrix_UB_13      0.0158591000
_diffrn_orient_matrix_UB_21      -0.0064150000
_diffrn_orient_matrix_UB_22      0.0981243000
_diffrn_orient_matrix_UB_23      0.0482423000
_diffrn_orient_matrix_UB_31      -0.0280608000
_diffrn_orient_matrix_UB_32      -0.0981991000
_diffrn_orient_matrix_UB_33      0.0462201000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11668
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.042
_diffrn_reflns_theta_max         67.042
_diffrn_reflns_theta_min         5.303
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.006
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0605
_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^)+(0.0998P)^2^+0.5541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1720
_refine_ls_wR_factor_ref         0.1835
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3125
_reflns_number_total             3844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra02638b2.cif
_cod_data_source_block           1
_cod_original_cell_volume        2155.09(14)
_cod_database_code               7228160
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23)
;
_shelx_res_checksum              85355
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'