Cu/Base Co-catalyzed [3 + 3] Cycloaddition for the Synthesis of Highly Functionalized 4-Fluoropyridines
Dong, Jinhuan; Feng, Wanzhong; Wang, Lei; Li, Mei; Chen, Zhe; Xu, Xianxiu; Chemical Communications  (2021) –; doi:10.1039/D1CC05412K

data_7129184
_publ_section_title
;
 Cu/Base Co-catalyzed [3 + 3] Cycloaddition for the Synthesis of Highly
 Functionalized 4-Fluoropyridines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05412K
_journal_year                    2021
_chemical_formula_moiety         'C14 H11 Cl F N O2'
_chemical_formula_sum            'C14 H11 Cl F N O2'
_chemical_formula_weight         279.69
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-12-23
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2021-04-11 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                103.627(7)
_cell_angle_beta                 97.874(8)
_cell_angle_gamma                98.131(7)
_cell_formula_units_Z            2
_cell_length_a                   7.3135(7)
_cell_length_b                   7.6484(6)
_cell_length_c                   12.3996(11)
_cell_measurement_reflns_used    1601
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8190
_cell_measurement_theta_min      6.2200
_cell_volume                     656.75(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9868
_diffrn_measured_fraction_theta_max 0.9697
_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    -70.00 -44.00   1.00    1.00    --    0.00 -37.00-150.00   26
  2  \w    -23.00  24.00   1.00    1.00    --    0.00 -37.00-150.00   47
  3  \w      5.00  58.00   1.00    1.00    --    0.00  57.00   0.00   53
  4  \w    -13.00  64.00   1.00    1.00    --   54.00 -57.00-180.00   77
  5  \w     23.00 102.00   1.00    1.00    --   54.00-125.00-180.00   79
  6  \w     72.00  98.00   1.00    1.00    --   54.00  57.00 120.00   26
  7  \w     75.00 100.00   1.00    1.00    --   54.00  57.00-150.00   25
  8  \w    -11.00  79.00   1.00    1.00    --   54.00 -77.00 -60.00   90
  9  \w     76.00 121.00   1.00    1.00    --   54.00  57.00 -30.00   45
 10  \w     28.00 121.00   1.00    1.00    --   54.00  37.00  90.00   93
 11  \w     41.00 129.00   1.00    1.00    --  108.00 -50.00 120.00   88
 12  \w     36.00 109.00   1.00    1.00    --  108.00-111.00 -30.00   73
 13  \w     85.00 151.00   1.00    1.00    --  108.00  37.00-120.00   66
 14  \w     39.00  74.00   1.00    1.00    --  108.00 -91.00 150.00   35
 15  \w    138.00 169.00   1.00    1.00    --  108.00  63.00 -90.00   31
 16  \w     86.00 121.00   1.00    1.00    --  108.00  63.00 -90.00   35
 17  \w     54.00 120.00   1.00    1.00    --  108.00 -77.00 -30.00   66
 18  \w     63.00 133.00   1.00    1.00    --  108.00 -37.00 -30.00   70
 19  \w     36.00 133.00   1.00    1.00    --  108.00 -37.00 -90.00   97
 20  \w     52.00 112.00   1.00    1.00    --  108.00-111.00 120.00   60
 21  \w    142.00 177.00   1.00    1.00    --  108.00  25.00  90.00   35
 22  \w    101.00 127.00   1.00    1.00    --  108.00 111.00 -30.00   26
 23  \w     82.00 143.00   1.00    1.00    --  108.00 -91.00 150.00   61
 24  \w    115.00 171.00   1.00    1.00    --  108.00  37.00 -30.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2082058000
_diffrn_orient_matrix_UB_12      -0.0189862000
_diffrn_orient_matrix_UB_13      0.0171620000
_diffrn_orient_matrix_UB_21      -0.0206459000
_diffrn_orient_matrix_UB_22      -0.0561415000
_diffrn_orient_matrix_UB_23      0.1097753000
_diffrn_orient_matrix_UB_31      -0.0544686000
_diffrn_orient_matrix_UB_32      -0.2022092000
_diffrn_orient_matrix_UB_33      -0.0672836000
_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  0.0210
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3825
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.01
_diffrn_reflns_theta_min         3.73
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0814P)^2^+0.1469P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1547
_reflns_number_gt                1864
_reflns_number_total             2312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc05412k2.cif
_cod_data_source_block           exp_3690
_cod_original_cell_volume        656.75(10)
_cod_database_code               7129184
_chemical_oxdiff_formula         'C1 H1 N1 O1 Cl1'
_reflns_odcompleteness_completeness 98.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C11(H11)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.670
_oxdiff_exptl_absorpt_empirical_full_min 0.675