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_7247727
_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 H16 F2 N2 O'
_chemical_formula_sum            'C17 H16 F2 N2 O'
_chemical_formula_weight         302.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-04-06
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf 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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   37.7194(4)
_cell_length_b                   16.9142(2)
_cell_length_c                   9.49011(12)
_cell_measurement_reflns_used    8539
_cell_measurement_temperature    294.60(10)
_cell_measurement_theta_max      75.4790
_cell_measurement_theta_min      5.4500
_cell_volume                     6054.63(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.60(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_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     84.00 178.00   0.50    0.80    --  109.26  26.00   7.00  188
  2  \w     80.00 178.00   0.50    0.80    --  109.26  77.00-120.00  196
  3  \w     90.00 118.00   0.50    0.80    --  109.26  30.00-180.00   56
  4  \w    125.00 177.00   0.50    0.80    --  109.26  30.00-180.00  104
  5  \w    -27.00  38.00   0.50    0.27    --  -43.18  19.00 120.00  130
  6  \w    -51.00 -14.00   0.50    0.80    --  -90.25  45.00 120.00   74
  7  \w    -51.00 -14.00   0.50    0.80    --  -90.25  45.00   0.00   74
  8  \w    -51.00 -14.00   0.50    0.80    --  -90.25  45.00  30.00   74
  9  \w    -32.00  36.00   0.50    0.27    --  -43.18  26.00   7.00  136
 10  \w     58.00  94.00   0.50    0.80    --  109.26-103.00  91.00   72
 11  \w     36.00 105.00   0.50    0.80    --  109.26 -94.00  30.00  138
 12  \w    -86.00 -13.00   0.50    0.27    --  -43.18 125.00-180.00  146
 13  \w    -81.00 -15.00   0.50    0.80    --  -90.25 103.00-166.00  132
 14  \w    -82.00 -15.00   0.50    0.80    --  -90.25 112.00  95.00  134
 15  \w    -36.00  32.00   0.50    0.27    --   43.18 -26.00-156.00  136
 16  \w     35.00 106.00   0.50    0.80    --  109.26 -77.00-180.00  142
 17  \w     35.00  71.00   0.50    0.80    --  109.26 -61.00 -90.00   72
 18  \w     35.00  71.00   0.50    0.80    --  109.26 -61.00 -30.00   72
 19  \w     35.00 106.00   0.50    0.80    --  109.26 -77.00 120.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0039474000
_diffrn_orient_matrix_UB_12      -0.0584249000
_diffrn_orient_matrix_UB_13      -0.1235441000
_diffrn_orient_matrix_UB_21      -0.0137158000
_diffrn_orient_matrix_UB_22      -0.0674732000
_diffrn_orient_matrix_UB_23      0.0943938000
_diffrn_orient_matrix_UB_31      -0.0382741000
_diffrn_orient_matrix_UB_32      0.0181410000
_diffrn_orient_matrix_UB_33      -0.0466123000
_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  0.0253
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10107
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.506
_diffrn_reflns_theta_min         4.689
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             2528
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1133 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0554P)^2^+1.3038P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.887
_reflns_Friedel_fraction_max     0.835
_reflns_number_gt                2752
_reflns_number_total             2875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03203e2.cif
_cod_data_source_block           pdp-31
_cod_depositor_comments
'Adding full bibliography for 7247725--7247728.cif.'
_cod_original_cell_volume        6054.64(13)
_cod_database_code               7247727
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C272 H256 N32 O48 '
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.898
_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 Ternary CH refined with riding coordinates:
 C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              16719
_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 1.515
_oxdiff_exptl_absorpt_empirical_full_min 0.579