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_7129183
_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_absolute_configuration ad
_chemical_formula_moiety         'C20 H16 F N O4 S'
_chemical_formula_sum            'C20 H16 F N O4 S'
_chemical_formula_weight         385.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-11-25
_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                90.00
_cell_angle_beta                 92.620(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.0579(2)
_cell_length_b                   15.5439(5)
_cell_length_c                   9.8183(3)
_cell_measurement_reflns_used    2208
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6650
_cell_measurement_theta_min      10.1960
_cell_volume                     923.56(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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 0.9930
_diffrn_measured_fraction_theta_max 0.7265
_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     -2.00  24.00   1.00    1.00    --    0.00  81.00 117.00   26
  2  \w    -16.00  67.00   1.00    1.00    --   54.00 -81.00  -5.00   83
  3  \w    139.00 164.00   1.00    1.00    --  108.00  81.00 117.00   25
  4  \w    107.00 134.00   1.00    1.00    --  108.00 -81.00  -5.00   27
  5  \w     43.00  80.00   1.00    1.00    --  108.00 -81.00  -5.00   37
  6  \w    -21.00  29.00   1.00    1.00    --    0.00 -81.00  -5.00   50
  7  \w    -17.00  32.00   1.00    1.00    --    0.00  77.00-150.00   49
  8  \w     31.00  56.00   1.00    1.00    --   54.00  37.00 -60.00   25
  9  \w     38.00  64.00   1.00    1.00    --   54.00-125.00 -30.00   26
 10  \w      9.00  75.00   1.00    1.00    --   54.00 -37.00   0.00   66
 11  \w     91.00 120.00   1.00    1.00    --   54.00  37.00 -60.00   29
 12  \w    -17.00  76.00   1.00    1.00    --   54.00 -37.00 120.00   93
 13  \w     37.00  65.00   1.00    1.00    --  108.00-111.00 -60.00   28
 14  \w     37.00 109.00   1.00    1.00    --  108.00-111.00-180.00   72
 15  \w    116.00 160.00   1.00    1.00    --  108.00 111.00 -60.00   44
 16  \w     38.00 107.00   1.00    1.00    --  108.00-111.00 -30.00   69
 17  \w     54.00  99.00   1.00    1.00    --  108.00 -91.00  60.00   45
 18  \w     36.00  91.00   1.00    1.00    --  108.00 -91.00-120.00   55
 19  \w     87.00 171.00   1.00    1.00    --  108.00  37.00 150.00   84
 20  \w    104.00 134.00   1.00    1.00    --  108.00 111.00  30.00   30
;
_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      0.2108177000
_diffrn_orient_matrix_UB_12      -0.0484971000
_diffrn_orient_matrix_UB_13      -0.0369432000
_diffrn_orient_matrix_UB_21      -0.1426630000
_diffrn_orient_matrix_UB_22      -0.0701808000
_diffrn_orient_matrix_UB_23      -0.0714556000
_diffrn_orient_matrix_UB_31      0.0041088000
_diffrn_orient_matrix_UB_32      0.0504523000
_diffrn_orient_matrix_UB_33      -0.1349070000
_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  0.0185
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3793
_diffrn_reflns_theta_full        70.35
_diffrn_reflns_theta_max         70.36
_diffrn_reflns_theta_min         5.33
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.877
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.029(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+0.0140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                2476
_reflns_number_total             2576
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc05412k2.cif
_cod_data_source_block           exp_18
_cod_database_code               7129183
_diffrn_oxdiff_digest_frames
;
015f691d374eb623ece29f956535fcd821000286224
;
_diffrn_oxdiff_digest_hkl
;
01b5a48ad5001fa4109ffec8960cc32ff09a41
;
_reflns_odcompleteness_completeness 99.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C15(H15), C16(H16), C18(H18),
 C19(H19)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.814