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_7129182
_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         'C18 H13 Cl F N O2 S'
_chemical_formula_sum            'C18 H13 Cl F N O2 S'
_chemical_formula_weight         361.80
_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             2020-10-09
_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                96.689(6)
_cell_angle_beta                 101.847(6)
_cell_angle_gamma                99.853(5)
_cell_formula_units_Z            4
_cell_length_a                   8.5995(5)
_cell_length_b                   11.0868(7)
_cell_length_c                   18.5904(14)
_cell_measurement_reflns_used    3031
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6730
_cell_measurement_theta_min      6.3290
_cell_volume                     1687.8(2)
_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 0.9970
_diffrn_measured_fraction_theta_max 0.9776
_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  67.00   1.00    1.00    --    0.00  57.00-120.00   48
  2  \w     33.00  69.00   1.00    1.00    --    0.00  57.00 -60.00   36
  3  \w    -63.00 -27.00   1.00    1.00    --    0.00 -57.00 150.00   36
  4  \w    -16.00  21.00   1.00    1.00    --    0.00 -57.00 150.00   37
  5  \w     26.00 104.00   1.00    1.45    --   54.00-125.00-120.00   78
  6  \w    -18.00  75.00   1.00    1.45    --   54.00 -37.00  60.00   93
  7  \w     36.00  86.00   1.00    1.45    --   54.00-125.00  90.00   50
  8  \w     77.00 123.00   1.00    1.45    --   54.00  37.00-120.00   46
  9  \w     15.00  80.00   1.00    1.45    --   54.00 -37.00-150.00   65
 10  \w     29.00  57.00   1.00    1.45    --   54.00  37.00-120.00   28
 11  \w     30.00 126.00   1.00    1.45    --   54.00  37.00  30.00   96
 12  \w     79.00 106.00   1.00    1.45    --  108.00-111.00  90.00   27
 13  \w     65.00 112.00   1.00    1.45    --  108.00-111.00-180.00   47
 14  \w     93.00 171.00   1.00    1.45    --  108.00  77.00-120.00   78
 15  \w     63.00 129.00   1.00    1.45    --  108.00 -63.00 -90.00   66
 16  \w    102.00 178.00   1.00    1.45    --  108.00  37.00 -60.00   76
 17  \w     38.00  69.00   1.00    1.45    --  108.00 -77.00  30.00   31
 18  \w    131.00 175.00   1.00    1.45    --  108.00  63.00 -30.00   44
 19  \w     86.00 128.00   1.00    1.45    --  108.00  63.00 -30.00   42
 20  \w     44.00 142.00   1.00    1.45    --  108.00 -91.00-150.00   98
 21  \w    112.00 137.00   1.00    1.45    --  108.00 178.00 150.00   25
 22  \w     41.00  97.00   1.00    1.45    --  108.00 -50.00  90.00   56
 23  \w     85.00 111.00   1.00    1.45    --  108.00-111.00   0.00   26
 24  \w     66.00 102.00   1.00    1.45    --  108.00 178.00 150.00   36
 25  \w     83.00 120.00   1.00    1.45    --  108.00 178.00-180.00   37
 26  \w     91.00 116.00   1.00    1.45    --  108.00  63.00 120.00   25
 27  \w     38.00 128.00   1.00    1.45    --  108.00 -50.00-180.00   90
 28  \w     87.00 112.00   1.00    1.45    --  108.00 -77.00  30.00   25
 29  \w     87.00 166.00   1.00    1.45    --  108.00  37.00  30.00   79
;
_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      0.0842983000
_diffrn_orient_matrix_UB_12      0.1311661000
_diffrn_orient_matrix_UB_13      -0.0066448000
_diffrn_orient_matrix_UB_21      -0.1040623000
_diffrn_orient_matrix_UB_22      -0.0137782000
_diffrn_orient_matrix_UB_23      -0.0796534000
_diffrn_orient_matrix_UB_31      -0.1302891000
_diffrn_orient_matrix_UB_32      0.0547775000
_diffrn_orient_matrix_UB_33      0.0310201000
_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  0.0260
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11108
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.10
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.345
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53924
_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 pale colourless'
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0708P)^2^+0.1033P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1447
_reflns_number_gt                4322
_reflns_number_total             6014
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc05412k2.cif
_cod_data_source_block           exp_3908
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C36 H26 Cl2 F2 N2 O4 S2'
_cod_original_formula_weight         723.61
_cod_original_formula_moiety         '2(C18 H13 Cl F N O2 S)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1687.83(19)
_cod_database_code               7129182
_chemical_oxdiff_usercomment     CHNOCl
_reflns_odcompleteness_completeness 99.70
_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:
 C19(H19A,H19B,H19C), C38(H38A,H38B,H38C)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C14(H14), C15(H15),
 C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C30(H30),
  C33(H33), C34(H34), C36(H36), C37(H37)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.024
_oxdiff_exptl_absorpt_empirical_full_min 0.686