Synthesis of fluorinated 3-aminobenzofurans via a tandem SNAr-cyclocondensation strategy
Tawell, Hugh W.; Robinson, William; Li, Yuqi; Tizzard, Graham J.; Coles, Simon J.; Bhambra, Avninder S.; Edgar, Mark; Weaver, George W.; RSC Advances 15 (2025) 12843–12853; doi:10.1039/D5RA02024G

data_7250296
_publ_section_title
;
 Synthesis of fluorinated 3-aminobenzofurans via a tandem
 SNAr-cyclocondensation strategy
;
_journal_issue                   16
_journal_name_full               'RSC Advances'
_journal_page_first              12843
_journal_page_last               12853
_journal_paper_doi               10.1039/D5RA02024G
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C20 H17 F3 N2 O4'
_chemical_formula_sum            'C20 H17 F3 N2 O4'
_chemical_formula_weight         406.35
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-11
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2023-12-08 deposited with the CCDC.	2025-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                73.3340(10)
_cell_angle_beta                 76.375(2)
_cell_angle_gamma                73.2360(10)
_cell_formula_units_Z            2
_cell_length_a                   7.23080(10)
_cell_length_b                   10.25330(10)
_cell_length_c                   12.8367(2)
_cell_measurement_reflns_used    25385
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.7160
_cell_measurement_theta_min      2.5620
_cell_volume                     860.78(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.942
_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    -24.00  94.00   0.50    0.50    --    5.00  57.00 120.00  236
  2  \w    -95.00  24.00   0.50    0.50    --   -5.70 -57.00 150.00  238
  3  \w    -95.00  25.00   0.50    0.50    --   -5.70 -38.00   0.00  240
  4  \w    -95.00  24.00   0.50    0.50    --   -5.70 -57.00 -90.00  238
  5  \w    -36.00  25.00   0.50    0.50    --   -5.70  38.00 -90.00  122
  6  \w    -36.00  84.00   0.50    0.50    --   -5.70  38.00  30.00  240
  7  \w    -84.00  35.00   0.50    0.50    --    5.00 -38.00  30.00  238
  8  \w    -95.00  25.00   0.50    0.50    --   -5.70 -38.00-150.00  240
  9  \w    -95.00  25.00   0.50    0.50    --   -5.70 -60.00 -30.00  240
 10  \w    -95.00  25.00   0.50    0.50    --   -5.70 -60.00 120.00  240
 11  \w    -84.00  35.00   0.50    0.50    --    5.00 -38.00 -90.00  238
 12  \w    -36.00  25.00   0.50    0.50    --   -5.70  38.00 150.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC12 \k goniometer'
_diffrn_measurement_device_type
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0596191000
_diffrn_orient_matrix_UB_12      0.0169904000
_diffrn_orient_matrix_UB_13      -0.0520224000
_diffrn_orient_matrix_UB_21      -0.0549967000
_diffrn_orient_matrix_UB_22      0.0705825000
_diffrn_orient_matrix_UB_23      -0.0077557000
_diffrn_orient_matrix_UB_31      0.0649332000
_diffrn_orient_matrix_UB_32      0.0159643000
_diffrn_orient_matrix_UB_33      0.0255993000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            42188
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         2.984
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_recrystallization_method
'The material was recrystallised from CDCl3 by slow evaporation'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0534P)^2^+0.2459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4429
_reflns_number_total             4967
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra02024g2.cif
_cod_data_source_block           4ed
_cod_database_code               7250296
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C40 H34 F6 N4 O8 '
_chemical_oxdiff_usercomment     GWWHT552b
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.977
_reflns_odcompleteness_completeness 94.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              55712
_olex2_date_sample_data_collection 2019-12-10
_olex2_date_sample_submission    2019-11-29
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id GWWHT552b
_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 1.521
_oxdiff_exptl_absorpt_empirical_full_min 0.711