Difluoromethylene Insertion into Fluoroalkyl Copper Complexes
Zhou, Yuyang; Doi, Ryohei; Ogoshi, Sensuke; Chemical Communications  (2023) –; doi:10.1039/D3CC03481J

data_7132067
_publ_section_title
;
 Difluoromethylene Insertion into Fluoroalkyl Copper Complexes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03481J
_journal_year                    2023
_chemical_formula_moiety         'C16 H9 F6 N'
_chemical_formula_sum            'C16 H9 F6 N'
_chemical_formula_weight         329.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-06-29 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.826(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2311(5)
_cell_length_b                   9.9935(3)
_cell_length_c                   13.5768(6)
_cell_measurement_reflns_used    7475
_cell_measurement_temperature    123
_cell_measurement_theta_max      76.5230
_cell_measurement_theta_min      3.5400
_cell_volume                     1393.97(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_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   -110.00 -38.00   0.50    0.05    -- -105.75 125.00 120.00  144
  2  \w    -75.00 -37.00   0.50    0.05    -- -105.75 125.00  60.00   76
  3  \w   -105.00 -37.00   0.50    0.05    -- -105.75 125.00   0.00  136
  4  \w    -99.00 -62.00   0.50    0.05    -- -105.75 125.00 -60.00   74
  5  \w    -75.00 -39.00   0.50    0.05    -- -105.75 107.00-110.70   72
  6  \w   -110.00 -44.00   0.50    0.05    -- -105.75 125.00-120.00  132
  7  \w   -107.00 -79.00   0.50    0.05    -- -105.75 107.00-110.70   56
  8  \w   -108.00 -59.00   0.50    0.05    -- -105.75 109.00 -30.96   98
  9  \w    -73.00 -36.00   0.50    0.05    -- -105.75 103.00  67.67   74
 10  \w   -105.00 -80.00   0.50    0.05    -- -105.75 103.00  67.67   50
 11  \w   -106.00 -76.00   0.50    0.05    -- -105.75 107.00 107.68   60
 12  \w    -60.00 -34.00   0.50    0.05    -- -105.75  33.00  34.00   52
 13  \w    -61.00 -36.00   0.50    0.05    -- -105.75  77.00 -30.00   50
 14  \w    -67.00 -35.00   0.50    0.05    -- -105.75  57.00 -30.00   64
 15  \w    -86.00 -45.00   0.50    0.05    -- -105.75  57.00 -90.00   82
 16  \w    -73.00 -44.00   0.50    0.05    -- -105.75  57.00-120.00   58
 17  \w    -63.00 -37.00   0.50    0.05    -- -105.75  37.00-120.00   52
 18  \w   -125.00-100.00   0.50    0.05    -- -105.75  77.00 -30.00   50
 19  \w    -87.00 -62.00   0.50    0.05    -- -105.75  57.00 120.00   50
 20  \w    -62.00 -36.00   0.50    0.05    -- -105.75  37.00  60.00   52
 21  \w    -42.00  16.00   0.50    0.05    --  -49.68  33.00  34.00  116
 22  \w     15.00  42.00   0.50    0.05    --   49.68 -57.00-120.00   54
 23  \w    -10.00  16.00   0.50    0.05    --   49.68 -33.00-123.00   52
 24  \w    -20.00  10.00   0.50    0.05    --   49.68 -57.00-120.00   60
 25  \w    -17.00   9.00   0.50    0.05    --   49.68 -37.00 -30.00   52
 26  \w     46.00 120.00   0.50    0.05    --   49.68  33.00  34.00  148
 27  \w     93.00 154.00   0.50    0.05    --   82.50  33.00  34.00  122
 28  \w    -23.00   5.00   0.50    0.05    --   49.68 -19.00  90.00   56
 29  \w    -23.00   2.00   0.50    0.05    --   49.68 -19.00 120.00   50
 30  \w     11.00  42.00   0.50    0.05    --   82.50 -57.00  90.00   62
 31  \w     17.00  44.00   0.50    0.05    --   82.50 -57.00 150.00   54
 32  \w     14.00  44.00   0.50    0.05    --   82.50 -57.00  60.00   60
 33  \w     14.00  39.00   0.50    0.05    --   82.50 -57.00 -90.00   50
 34  \w     19.00  45.00   0.50    0.05    --   49.68-125.00  60.00   52
 35  \w     52.00  90.00   0.50    0.05    --   49.68-125.00  60.00   76
 36  \w     14.00  67.00   0.50    0.05    --   82.50 -99.00 150.00  106
 37  \w   -118.00 -43.00   0.50    0.05    --  -49.68 -33.00-123.00  150
 38  \w   -177.00-100.00   0.50    0.05    -- -105.75 -37.00 -30.00  154
 39  \w   -169.00-103.00   0.50    0.05    -- -105.75 -33.00-123.00  132
 40  \w   -170.00-106.00   0.50    0.05    -- -105.75 -37.00   0.00  128
 41  \w   -141.00-100.00   0.50    0.05    -- -105.75 -19.00  60.00   82
 42  \w   -136.00-109.00   0.50    0.05    -- -105.75 -37.00 120.00   54
 43  \w   -176.00-144.00   0.50    0.05    -- -105.75 -37.00 120.00   64
 44  \w   -173.00-120.00   0.50    0.05    -- -105.75-125.00  30.00  106
 45  \w   -165.00-108.00   0.50    0.05    -- -105.75 -99.00 -90.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16159
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         4.303
_exptl_absorpt_coefficient_mu    1.321
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hot hexane'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0627P)^2^+0.2668P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2188
_reflns_number_total             2489
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03481j2.cif
_cod_data_source_block           syu_214_take3_auto
_cod_database_code               7132067
_shelx_shelxl_version_number     2019/2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00L(H00L), C00M(H00M), C00N(H00N)
;
_shelx_res_checksum              76858
_shelx_hkl_checksum              45899
_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
;