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

data_7132066
_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         'C15 H9 F4 N'
_chemical_formula_sum            'C15 H9 F4 N'
_chemical_formula_weight         279.23
_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             2023-06-06
_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                 90.679(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8964(3)
_cell_length_b                   5.82860(10)
_cell_length_c                   14.9634(4)
_cell_measurement_reflns_used    6882
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.0660
_cell_measurement_theta_min      5.9310
_cell_volume                     1211.90(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_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    -19.00   8.00   0.50    0.05    --   47.45 -77.00 150.00   54
  2  \w     14.00  70.00   0.50    0.05    --   47.45 -77.00 150.00  112
  3  \w     52.00 120.00   0.50    0.05    --   47.45  57.00   0.00  136
  4  \w     96.00 122.00   0.50    0.21    --   86.25 110.00  17.00   52
  5  \w    -19.00  19.00   0.50    0.05    --   47.45 -37.00-180.00   76
  6  \w    -27.00  -2.00   0.50    0.05    --   47.45 -19.00-150.00   50
  7  \w    -10.00  20.00   0.50    0.05    --   47.45 -37.00-150.00   60
  8  \w    -27.00   5.00   0.50    0.05    --   47.45 -19.00-120.00   64
  9  \w    -23.00   5.00   0.50    0.05    --   47.45 -19.00  90.00   56
 10  \w     17.00  42.00   0.50    0.21    --   86.25 -57.00  90.00   50
 11  \w     16.00  44.00   0.50    0.21    --   86.25 -57.00  30.00   56
 12  \w     15.00  42.00   0.50    0.21    --   86.25 -57.00 -90.00   54
 13  \w   -107.00 -81.00   0.50    0.21    -- -107.75 125.00 -60.00   52
 14  \w    -71.00 -38.00   0.50    0.21    -- -107.75 125.00-120.00   66
 15  \w   -106.00 -80.00   0.50    0.21    -- -107.75 125.00-120.00   52
 16  \w   -103.00 -53.00   0.50    0.21    -- -107.75 125.00  30.00  100
 17  \w    -65.00 -40.00   0.50    0.21    -- -107.75 137.00  55.09   50
 18  \w   -120.00 -95.00   0.50    0.21    -- -107.75 137.00  55.09   50
 19  \w    -84.00 -10.00   0.50    0.05    --  -47.45 110.00  17.00  148
 20  \w    -98.00 -62.00   0.50    0.21    -- -107.75 125.00 150.00   72
 21  \w   -110.00 -84.00   0.50    0.21    -- -107.75 125.00  90.00   52
 22  \w   -111.00 -86.00   0.50    0.21    -- -107.75 125.00  60.00   50
 23  \w   -107.00 -81.00   0.50    0.21    -- -107.75 110.00  17.00   52
 24  \w    -63.00 -37.00   0.50    0.21    -- -107.75  37.00 -90.00   52
 25  \w    -76.00 -35.00   0.50    0.21    -- -107.75  77.00  30.00   82
 26  \w   -123.00 -81.00   0.50    0.21    -- -107.75  77.00  30.00   84
 27  \w   -126.00 -97.00   0.50    0.21    -- -107.75  77.00 -60.00   58
 28  \w    -81.00 -55.00   0.50    0.21    -- -107.75  77.00 -60.00   52
 29  \w    -87.00 -37.00   0.50    0.21    -- -107.75  57.00-180.00  100
 30  \w    -77.00 -35.00   0.50    0.21    -- -107.75  57.00 -90.00   84
 31  \w    -73.00 -40.00   0.50    0.21    -- -107.75  57.00  30.00   66
 32  \w    -60.00 -35.00   0.50    0.21    -- -107.75  37.00  60.00   50
 33  \w    -87.00 -50.00   0.50    0.21    -- -107.75  57.00 150.00   74
 34  \w     10.00  45.00   0.50    0.05    --   47.45-110.00 -78.00   70
 35  \w     39.00  66.00   0.50    0.21    --   86.25-110.00 -78.00   54
 36  \w    -63.00 -34.00   0.50    0.21    -- -107.75  37.00-120.00   58
 37  \w    -60.00 -34.00   0.50    0.21    -- -107.75  37.00   0.00   52
 38  \w   -175.00-101.00   0.50    0.21    -- -107.75 -19.00  60.00  148
 39  \w   -171.00 -95.00   0.50    0.21    -- -107.75 -37.00 150.00  152
 40  \w   -138.00 -86.00   0.50    0.21    -- -107.75 -77.00  60.00  104
 41  \w   -177.00 -96.00   0.50    0.21    -- -107.75 -37.00-180.00  162
 42  \w   -153.00-125.00   0.50    0.21    -- -107.75-110.00 -78.00   56
 43  \w   -107.00 -82.00   0.50    0.21    -- -107.75-110.00 -78.00   50
 44  \w   -117.00 -74.00   0.50    0.21    -- -107.75-125.00 -30.00   86
 45  \w   -170.00-144.00   0.50    0.21    -- -107.75-125.00 -30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0589200000
_diffrn_orient_matrix_UB_12      0.0042586000
_diffrn_orient_matrix_UB_13      -0.0865274000
_diffrn_orient_matrix_UB_21      0.0847702000
_diffrn_orient_matrix_UB_22      0.1114815000
_diffrn_orient_matrix_UB_23      0.0511325000
_diffrn_orient_matrix_UB_31      0.0404595000
_diffrn_orient_matrix_UB_32      -0.2396125000
_diffrn_orient_matrix_UB_33      0.0223004000
_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  0.0493
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12705
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         5.915
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.162
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_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         0.222
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0506P)^2^+0.3263P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2006
_reflns_number_total             2209
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03481j2.cif
_cod_data_source_block           syu374_auto
_cod_database_code               7132066
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         C15H9F4N
_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), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K)
;
_shelx_res_checksum              16149
_shelx_hkl_checksum              33298
_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 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.754