Practical conversion of gem-difluorocyclopropenes for the chemodivergent assembly of fluorinated heterocyclic frameworks
Pan, Dongping; Liu, Fu-Xiaomin; Zeng, Zhongyi; Ye, Junwei; Cai, Ying; Wang, Shengdong; Zhou, Zhi; Yi, Wei; Green Chemistry 25 (2023) 10630–10637; doi:10.1039/D3GC03203E

data_7247726
_publ_section_title
;
 Practical conversion of gem-difluorocyclopropenes for the chemodivergent
 assembly of fluorinated heterocyclic frameworks
;
_journal_issue                   24
_journal_name_full               'Green Chemistry'
_journal_page_first              10630
_journal_page_last               10637
_journal_paper_doi               10.1039/D3GC03203E
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C17 H15 F N2 O2'
_chemical_formula_sum            'C17 H15 F N2 O2'
_chemical_formula_weight         298.31
_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             2023-03-30
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-07-07 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                67.050(6)
_cell_angle_beta                 88.220(4)
_cell_angle_gamma                71.172(5)
_cell_formula_units_Z            2
_cell_length_a                   8.8203(5)
_cell_length_b                   9.1068(6)
_cell_length_c                   10.6468(6)
_cell_measurement_reflns_used    3642
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.7350
_cell_measurement_theta_min      5.5820
_cell_volume                     740.95(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.964
_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  77.00   1.00    1.00    --   40.73 -99.00 -90.00   74
  2  \w     80.00 122.00   1.00    1.00    --  107.58-125.00 -30.00   42
  3  \w    100.00 126.00   1.00    1.00    --  107.58 -45.00  60.00   26
  4  \w     63.00 118.00   1.00    1.00    --  107.58 -61.00 150.00   55
  5  \w     51.00 108.00   1.00    1.00    --  107.58 -94.00 150.00   57
  6  \w     50.00  81.00   1.00    1.00    --   40.73-125.00  60.00   31
  7  \w     35.00  81.00   1.00    1.00    --  107.58 -45.00  60.00   46
  8  \w     27.00 106.00   1.00    1.00    --  107.58 -94.00  60.00   79
  9  \w     31.00  95.00   1.00    1.00    --  107.58 -30.00-120.00   64
 10  \w     83.00 173.00   1.00    1.00    --  107.58  30.00-180.00   90
 11  \w     93.00 167.00   1.00    1.00    --  107.58  45.00 -90.00   74
 12  \w    150.00 176.00   1.00    1.00    --  107.58 102.00  63.00   26
 13  \w    114.00 178.00   1.00    1.00    --  107.58 125.00 120.00   64
 14  \w     79.00 177.00   1.00    1.00    --  107.58  61.00-150.00   98
 15  \w      2.00  58.00   1.00    1.00    --   40.73 -99.00-180.00   56
 16  \w   -115.00 -16.00   1.00    1.00    --  -40.73 -37.00  30.00   99
 17  \w   -115.00 -17.00   1.00    1.00    --  -40.73 -37.00 -60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0367046000
_diffrn_orient_matrix_UB_12      0.0874228000
_diffrn_orient_matrix_UB_13      -0.1478291000
_diffrn_orient_matrix_UB_21      -0.1684671000
_diffrn_orient_matrix_UB_22      0.1361700000
_diffrn_orient_matrix_UB_23      -0.0325529000
_diffrn_orient_matrix_UB_31      0.0687932000
_diffrn_orient_matrix_UB_32      0.1090937000
_diffrn_orient_matrix_UB_33      0.0455397000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4658
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.778
_diffrn_reflns_theta_min         4.537
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.064(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0971P)^2^+0.2843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1585
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2684
_reflns_number_total             2887
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03203e2.cif
_cod_data_source_block           244
_cod_depositor_comments
'Adding full bibliography for 7247725--7247728.cif.'
_cod_database_code               7247726
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              27882
_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 11.768
_oxdiff_exptl_absorpt_empirical_full_min 0.530