Nucleophilic aromatic substitution of non-activated aryl fluorides with aliphatic amides
Matsuura, Akihisa; Ano, Yusuke; Chatani, Naoto; Chemical Communications  (2022) –; doi:10.1039/D2CC02999E

data_7130504
_publ_section_title
;
 Nucleophilic aromatic substitution of non-activated aryl fluorides with
 aliphatic amides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02999E
_journal_year                    2022
_chemical_formula_moiety         'C17 H26 B N O3'
_chemical_formula_sum            'C17 H26 B N O3'
_chemical_formula_weight         303.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-07-05 deposited with the CCDC.	2022-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                70.722(4)
_cell_angle_beta                 85.965(4)
_cell_angle_gamma                89.751(4)
_cell_formula_units_Z            2
_cell_length_a                   6.4832(3)
_cell_length_b                   11.8496(6)
_cell_length_c                   11.9710(5)
_cell_measurement_reflns_used    4608
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.2140
_cell_measurement_theta_min      2.9600
_cell_volume                     865.76(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.794
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -3.00  60.00   0.50    7.38    --   -4.17  68.00-125.00  126
  2  \w    -26.00  29.00   0.50    7.38    --   -4.17 -99.00 -60.00  110
  3  \w    -19.00  25.00   0.50    7.38    --    4.56 -99.00 -90.00   88
  4  \w    -26.00  29.00   0.50    7.38    --   -4.17 -99.00-180.00  110
  5  \w    -67.00 -16.00   0.50    7.38    --    4.56 -38.00-150.00  102
  6  \w    -13.00  26.00   0.50    7.38    --   -4.17 -99.00  90.00   78
  7  \w    -76.00  10.00   0.50    7.38    --   -4.17 -68.00 101.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0468686000
_diffrn_orient_matrix_UB_12      0.0101985000
_diffrn_orient_matrix_UB_13      0.0476877000
_diffrn_orient_matrix_UB_21      -0.0542786000
_diffrn_orient_matrix_UB_22      0.0541858000
_diffrn_orient_matrix_UB_23      -0.0103352000
_diffrn_orient_matrix_UB_31      -0.0830139000
_diffrn_orient_matrix_UB_32      -0.0313516000
_diffrn_orient_matrix_UB_33      0.0397545000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.794
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12100
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.794
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.664
_diffrn_reflns_theta_min         1.821
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.163
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.147
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         4253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0641P)^2^+0.2077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1454
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3002
_reflns_number_total             4253
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02999e2.cif
_cod_data_source_block           exp_598
_cod_database_code               7130504
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H26 B1 N1 O3'
_chemical_oxdiff_usercomment     220704_MATSUURA_864_Mo
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.980
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3), C6(H6)
2.c Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c), C15(H15a,H15b,H15c), C14(H14a,H14b,H14c), C12(H12a,H12b,
 H12c), C19(H19a,H19b,H19c), C13(H13a,H13b,H13c), C20(H20a,H20b,H20c)
;
_shelx_res_checksum              71768
_shelx_hkl_checksum              73154
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.121
_oxdiff_exptl_absorpt_empirical_full_min 0.627