Nucleophilic Trifluoromethylation of Electron-Deficient Arenes
Pike, Jack A.; Walton, James William; Chem. Commun.  (2017) –; doi:10.1039/C7CC05415G

data_7120546
_publ_section_title
;
 Nucleophilic Trifluoromethylation of Electron-Deficient Arenes
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC05415G
_journal_year                    2017
_chemical_formula_moiety         'C11 H10 N O2 Ru, F6 P'
_chemical_formula_sum            'C11 H10 F6 N O2 P Ru'
_chemical_formula_weight         434.24
_chemical_name_systematic
;
 ? 
;
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-02-26
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-04-27 deposited with the CCDC.
2017-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.5709(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.17160(16)
_cell_length_b                   12.4722(2)
_cell_length_c                   13.2874(3)
_cell_measurement_reflns_used    7382
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      32.7780
_cell_measurement_theta_min      2.2250
_cell_volume                     1353.71(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega    4.00   68.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000   90.0000 64

  2 omega    2.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000    0.0000 91

  3 omega    6.00   71.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000 -180.0000 65

  4 omega  -26.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587    0.0000 -150.0000 127

  5 omega  -41.00   59.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -77.0000 -120.0000 100

  6 omega   35.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  178.0000  150.0000 70

  7 omega  -40.00   32.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -57.0000  120.0000 72

  8 omega    9.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000  -90.0000 89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0687882000
_diffrn_orient_matrix_UB_12      -0.0222013000
_diffrn_orient_matrix_UB_13      -0.0262110000
_diffrn_orient_matrix_UB_21      -0.0205896000
_diffrn_orient_matrix_UB_22      0.0514692000
_diffrn_orient_matrix_UB_23      -0.0191633000
_diffrn_orient_matrix_UB_31      0.0488303000
_diffrn_orient_matrix_UB_32      -0.0095541000
_diffrn_orient_matrix_UB_33      -0.0424057000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20965
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.24
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.352
_exptl_absorpt_correction_T_max  0.776
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.131
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.23
_refine_diff_density_max         1.289
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+1.8590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                3392
_reflns_number_total             3953
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc05415g2.cif
_cod_data_source_block           2_16srv082
_cod_original_cell_volume        1353.72(5)
_cod_database_code               7120546
_chemical_oxdiff_formula         'C11 H10 N1 O2 P1 F6 Ru1'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11)
;