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

data_7132068
_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         'C17 H9 F8 N'
_chemical_formula_sum            'C17 H9 F8 N'
_chemical_formula_weight         379.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 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                 106.035(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.9150(17)
_cell_length_b                   5.0800(3)
_cell_length_c                   27.5806(19)
_cell_measurement_reflns_used    3337
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.9220
_cell_measurement_theta_min      4.0030
_cell_volume                     3085.7(4)
_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    -17.00  19.00   0.50    0.10    --   49.93 -37.00 120.00   72
  2  \w    -20.00  20.00   0.50    0.10    --   49.93 -37.00  90.00   80
  3  \w    -21.00   4.00   0.50    0.10    --   49.93 -19.00   0.00   50
  4  \w    -22.00   4.00   0.50    0.10    --   49.93 -19.00  30.00   52
  5  \w    -22.00   4.00   0.50    0.10    --   49.93 -19.00 -30.00   52
  6  \w    -22.00   3.00   0.50    0.10    --   49.93 -19.00 -60.00   50
  7  \w    -22.00   3.00   0.50    0.10    --   49.93 -19.00-120.00   50
  8  \w     36.00  62.00   0.50    0.10    --   82.50-111.00  36.00   52
  9  \w    -60.00   4.00   0.50    0.10    --  -49.93  57.00 120.00  128
 10  \w    -47.00 -21.00   0.50    0.10    --  -49.93  19.00-180.00   52
 11  \w     20.00  45.00   0.50    0.10    --   49.93-111.00  36.00   50
 12  \w     19.00  44.00   0.50    0.10    --   82.50 -57.00 -60.00   50
 13  \w     11.00  43.00   0.50    0.10    --   82.50 -57.00 -90.00   64
 14  \w     12.00  39.00   0.50    0.10    --   82.50 -57.00 150.00   54
 15  \w   -177.00 -99.00   0.50    0.10    -- -105.75 -37.00 120.00  156
 16  \w   -166.00-127.00   0.50    0.10    -- -105.75 -37.00 -30.00   78
 17  \w   -176.00-151.00   0.50    0.10    -- -105.75 -19.00-120.00   50
 18  \w   -145.00 -98.00   0.50    0.10    -- -105.75 -19.00-120.00   94
 19  \w   -134.00 -98.00   0.50    0.10    -- -105.75 -19.00-150.00   72
 20  \w   -168.00-138.00   0.50    0.10    -- -105.75 -19.00-150.00   60
 21  \w   -135.00 -82.00   0.50    0.10    -- -105.75-111.00  36.00  106
 22  \w    -85.00 -35.00   0.50    0.10    -- -105.75  57.00  60.00  100
 23  \w    -71.00 -46.00   0.50    0.10    -- -105.75  57.00  90.00   50
 24  \w    -79.00 -40.00   0.50    0.10    -- -105.75  57.00 120.00   78
 25  \w    -86.00 -53.00   0.50    0.10    -- -105.75  57.00 -60.00   66
 26  \w   -122.00 -72.00   0.50    0.10    -- -105.75  77.00 -90.00  100
 27  \w    -82.00 -41.00   0.50    0.10    -- -105.75  57.00-180.00   82
 28  \w    -62.00 -37.00   0.50    0.10    -- -105.75  37.00-150.00   50
 29  \w    -86.00 -37.00   0.50    0.10    -- -105.75  57.00 -90.00   98
 30  \w    -63.00 -38.00   0.50    0.10    -- -105.75  37.00 -30.00   50
 31  \w    -60.00 -35.00   0.50    0.10    -- -105.75  37.00   0.00   50
 32  \w    -63.00 -34.00   0.50    0.10    -- -105.75  37.00  60.00   58
 33  \w    -63.00 -35.00   0.50    0.10    -- -105.75  37.00 120.00   56
 34  \w    -80.00 -39.00   0.50    0.10    --  -49.93 111.00 130.00   82
 35  \w   -110.00 -85.00   0.50    0.10    -- -105.75 125.00 150.00   50
 36  \w    -79.00 -41.00   0.50    0.10    -- -105.75 125.00  60.00   76
 37  \w   -110.00 -81.00   0.50    0.10    -- -105.75 125.00  30.00   58
 38  \w    -94.00 -64.00   0.50    0.10    -- -105.75 125.00 -30.00   60
 39  \w   -110.00 -69.00   0.50    0.10    -- -105.75 125.00 -90.00   82
 40  \w    -99.00 -40.00   0.50    0.10    -- -105.75 125.00-120.00  118
 41  \w   -109.00 -37.00   0.50    0.10    -- -105.75 125.00 -60.00  144
 42  \w   -108.00 -74.00   0.50    0.10    -- -105.75 111.00 130.00   68
 43  \w    -68.00 -42.00   0.50    0.10    -- -105.75 125.00 150.00   52
 44  \w    -27.00  -2.00   0.50    0.10    --  -49.93 111.00 130.00   50
 45  \w     84.00 120.00   0.50    0.10    --   82.50 111.00 130.00   72
 46  \w     74.00 119.00   0.50    0.10    --   49.93 125.00  30.00   90
 47  \w     84.00 119.00   0.50    0.10    --   49.93 125.00 -90.00   70
;
_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  0.0986
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            17219
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.051
_diffrn_reflns_theta_max         67.051
_diffrn_reflns_theta_min         3.335
_exptl_absorpt_coefficient_mu    1.476
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78569
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_description       needle
_exptl_crystal_F_000             1520
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hot hexane'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0886P)^2^+1.3286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1598
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2085
_reflns_number_total             2747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03481j2.cif
_cod_data_source_block           syu_214_c4_auto
_cod_database_code               7132068
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.866
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00O(H00O), C00P(H00P), C00Q(H00Q)
;
_shelx_res_checksum              37244
_shelx_hkl_checksum              20262
_olex2_exptl_crystal_mounting_method Loop
_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
;