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_7247725
_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         'C21 H17 Br F2 N2 O'
_chemical_formula_sum            'C21 H17 Br F2 N2 O'
_chemical_formula_weight         431.27
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-24
_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                90
_cell_angle_beta                 110.294(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5594(7)
_cell_length_b                   19.9216(15)
_cell_length_c                   10.3113(8)
_cell_measurement_reflns_used    3205
_cell_measurement_temperature    220.03(10)
_cell_measurement_theta_max      26.3590
_cell_measurement_theta_min      2.9160
_cell_volume                     1841.8(3)
_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      220.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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 -49.00   1.00    5.00    --  -11.27 -57.00 -90.00   35
  2  \w    -33.00  32.00   1.00    5.00    --   11.90 -38.00 120.00   65
  3  \w    -20.00  84.00   1.00    5.00    --   11.90  77.00  60.00  104
;
_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      0.0611620000
_diffrn_orient_matrix_UB_12      -0.0003240000
_diffrn_orient_matrix_UB_13      0.0632803000
_diffrn_orient_matrix_UB_21      0.0052708000
_diffrn_orient_matrix_UB_22      -0.0353916000
_diffrn_orient_matrix_UB_23      -0.0048499000
_diffrn_orient_matrix_UB_31      0.0498448000
_diffrn_orient_matrix_UB_32      0.0041191000
_diffrn_orient_matrix_UB_33      -0.0367325000
_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  0.0368
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8451
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.045
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.265
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67432
_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    1.555
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0391P)^2^+0.3064P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2550
_reflns_number_total             3249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03203e2.cif
_cod_data_source_block           120-9
_cod_depositor_comments
'Adding full bibliography for 7247725--7247728.cif.'
_cod_database_code               7247725
_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 Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              30807
_olex2_date_sample_data_collection 2023-04-23
_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 1.219
_oxdiff_exptl_absorpt_empirical_full_min 0.784