Silver/palladium relay catalyzed 1,3-dipole annulation/allylation reactions to access fully substituted allyl imidazolidines.
Han, Ruiping; Ding, Yue; Jin, Xueke; Li, Er-Qing; Organic & biomolecular chemistry 18 (2020) 646–649; doi:10.1039/c9ob02633a

data_7157276
_publ_section_title
;
 Silver/palladium relay catalyzed 1,3-dipole annulation/allylation
 reactions to access fully substituted allyl imidazolidines.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              646
_journal_page_last               649
_journal_paper_doi               10.1039/c9ob02633a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C32 H33 F N2 O6'
_chemical_formula_sum            'C32 H33 F N2 O6'
_chemical_formula_weight         560.60
_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     direct
_audit_block_doi                 10.5517/ccdc.csd.cc23tj0h
_audit_creation_date             2019-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-23 deposited with the CCDC.	2019-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.4004(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.31491(15)
_cell_length_b                   22.9483(3)
_cell_length_c                   13.02398(18)
_cell_measurement_reflns_used    5371
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2250
_cell_measurement_theta_min      3.9500
_cell_volume                     3022.08(7)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_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    -49.00 -23.00   0.50    1.25    --  -33.50  81.00 -92.00   52
  2  \w   -102.00 -62.00   0.50    1.25    --  -33.50 -57.00 150.00   80
  3  \w    -50.00 -20.00   0.50    1.25    --  -33.50  57.00  30.00   60
  4  \w    -83.00 -36.00   0.50    1.25    --  -33.50 -57.00  60.00   94
  5  \w    -57.00 -15.00   0.50    1.25    --  -33.50 -57.00 150.00   84
  6  \w     -8.00  36.00   0.50    1.25    --  -33.50  81.00 -92.00   88
  7  \w    -11.00  31.00   0.50    1.25    --  -33.50  57.00  30.00   84
  8  \w    -32.00  65.00   0.50    1.25    --   36.47 -77.00-120.00  194
  9  \w     57.00  83.00   0.50    1.25    --   36.47 178.00 -90.00   52
 10  \w     38.00  64.00   0.50    1.25    --   36.47 -99.00 120.00   52
 11  \w     19.00  97.00   0.50    1.25    --   36.47  57.00 120.00  156
 12  \w     27.00  53.00   0.50    1.25    --   36.47  19.00 -90.00   52
 13  \w     14.00  75.00   0.50    1.25    --   36.47  37.00  60.00  122
 14  \w     75.00 109.00   0.50    1.25    --   36.47 178.00-180.00   68
 15  \w     57.00  82.00   0.50    1.25    --   36.47 178.00-120.00   50
 16  \w     12.00  38.00   0.50    1.25    --   36.47  19.00  60.00   52
 17  \w     58.00 107.00   0.50    1.25    --   36.47 178.00  90.00   98
 18  \w     61.00 107.00   0.50    1.25    --   36.47  19.00  60.00   92
 19  \w     -2.00  23.00   0.50    1.25    --   36.47 -99.00 120.00   50
 20  \w     67.00  93.00   0.50    1.25    --   36.47  19.00 -90.00   52
 21  \w     58.00  86.00   0.50    1.25    --   36.47 178.00 -60.00   56
 22  \w    101.00 178.00   0.50   12.50    --  108.00  81.00 -92.00  154
 23  \w    135.00 170.00   0.50   12.50    --  108.00  61.00 -60.00   70
 24  \w     61.00 109.00   0.50   12.50    --  108.00 -94.00-120.00   96
 25  \w     88.00 121.00   0.50   12.50    --  108.00  61.00 -60.00   66
 26  \w     59.00  95.00   0.50   12.50    --  108.00 -94.00-150.00   72
 27  \w     64.00 104.00   0.50   12.50    --  108.00  15.00  30.00   80
 28  \w     81.00 106.00   0.50   12.50    --  108.00 -61.00-120.00   50
 29  \w    105.00 151.00   0.50   12.50    --  108.00 111.00-180.00   92
 30  \w     44.00  72.00   0.50   12.50    --  108.00   0.00-180.00   56
 31  \w     82.00 131.00   0.50   12.50    --  108.00  30.00  60.00   98
 32  \w     53.00 112.00   0.50   12.50    --  108.00-111.00 150.00  118
 33  \w    105.00 175.00   0.50   12.50    --  108.00  61.00-150.00  140
 34  \w    113.00 176.00   0.50   12.50    --  108.00  77.00 -30.00  126
 35  \w    136.00 173.00   0.50   12.50    --  108.00 111.00 -60.00   74
 36  \w     80.00 107.00   0.50   12.50    --  108.00  77.00 -30.00   54
 37  \w    121.00 178.00   0.50   12.50    --  108.00  30.00  30.00  114
 38  \w     90.00 116.00   0.50   12.50    --  108.00  30.00  30.00   52
 39  \w     38.00 117.00   0.50   12.50    --  108.00 -45.00-150.00  158
 40  \w     38.00 111.00   0.50   12.50    --  108.00-111.00  60.00  146
 41  \w    102.00 164.00   0.50   12.50    --  108.00   0.00-180.00  124
 42  \w    141.00 176.00   0.50   12.50    --  108.00  77.00   0.00   70
 43  \w     79.00 105.00   0.50   12.50    --  108.00  77.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0626079000
_diffrn_orient_matrix_UB_12      -0.0520234000
_diffrn_orient_matrix_UB_13      0.0665917000
_diffrn_orient_matrix_UB_21      -0.1386835000
_diffrn_orient_matrix_UB_22      -0.0252328000
_diffrn_orient_matrix_UB_23      -0.0013501000
_diffrn_orient_matrix_UB_31      0.0072147000
_diffrn_orient_matrix_UB_32      -0.0340945000
_diffrn_orient_matrix_UB_33      -0.1006571000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23672
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.852
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80770
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       prism
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5396
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0773P)^2^+0.4204P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1541
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4065
_reflns_number_total             5396
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02633a2.cif
_cod_data_source_block           201909243
_cod_depositor_comments          'Adding full bibliography for 7157276.cif.'
_cod_database_code               7157276
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20O4N1F1
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.891
_reflns_odcompleteness_completeness 99.96
_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. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C17)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C13(H13), C14(H14), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C22(H22A,H22B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C21(H21), C20(H20), C19(H19),
 C18(H18), C17(H17), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
3.d Fitted hexagon refined as free rotating group:
 C16(C21,C20,C19,C18,C17), C25(C26,C27,C28,C29,C30)
3.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C24(H24A,H24B,H24C), C32(H32A,H32B,H32C)
;
_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 1.184
_oxdiff_exptl_absorpt_empirical_full_min 0.900