Silver(I)-catalyzed Domino Cyclization/Cyclopropanation/Ring-Cleavage/Nucleophilic Substitution Reaction of Enynones with Enamines: Synthesis of 4-(furan-2-yl)-3,4-dihydro-2<i>H</i>-pyrrol-2-one.
Peng, Haiyun; Zhang, Yu; Zhu, Yang; Deng, Guisheng; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01711

data_4038846
_publ_section_title
;
 Silver(I)-catalyzed Domino
 Cyclization/Cyclopropanation/Ring-Cleavage/Nucleophilic Substitution
 Reaction of Enynones with Enamines: Synthesis of
 4-(furan-2-yl)-3,4-dihydro-2<i>H</i>-pyrrol-2-one.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01711
_journal_year                    2020
_chemical_formula_moiety         'C18 H16 Cl N O3'
_chemical_formula_sum            'C18 H16 Cl N O3'
_chemical_formula_weight         329.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.6447(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.01784(17)
_cell_length_b                   10.98794(13)
_cell_length_c                   15.5845(2)
_cell_measurement_reflns_used    11388
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.5940
_cell_measurement_theta_min      4.7160
_cell_volume                     1651.92(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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 8.0697
_diffrn_detector_type            EosS2
_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    -35.00  64.00   1.00    1.00    --   34.73 -19.00-120.00   99
  2  \w     51.00  98.00   1.00    1.00    --   34.73  38.00 -30.00   47
  3  \w     68.00  98.00   1.00    1.00    --   34.73  77.00 -30.00   30
  4  \w     60.00  86.00   1.00    1.00    --   34.73  57.00  30.00   26
  5  \w     61.00  97.00   1.00    1.00    --   34.73  57.00  60.00   36
  6  \w     29.00  58.00   1.00    1.00    --   34.73  57.00  30.00   29
  7  \w     22.00  51.00   1.00    1.00    --   34.73  57.00  60.00   29
  8  \w      8.00  65.00   1.00    1.00    --   34.73  77.00  60.00   57
  9  \w     19.00  48.00   1.00    1.00    --   34.73  38.00 -30.00   29
 10  \w     11.00  52.00   1.00    1.00    --   34.73  77.00 -30.00   41
 11  \w      9.00  43.00   1.00    1.00    --   34.73  77.00 -90.00   34
 12  \w     18.00  90.00   1.00    1.00    --   34.73  57.00-120.00   72
 13  \w    113.00 173.00   1.00    4.00    --  105.88  77.00-180.00   60
 14  \w    125.00 156.00   1.00    4.00    --  105.88  77.00-150.00   31
 15  \w    118.00 172.00   1.00    4.00    --  105.88  77.00 -90.00   54
 16  \w    125.00 157.00   1.00    4.00    --  105.88  77.00 -60.00   32
 17  \w    130.00 172.00   1.00    4.00    --  105.88  61.00   0.00   42
 18  \w    141.00 167.00   1.00    4.00    --  105.88  77.00  30.00   26
 19  \w    125.00 168.00   1.00    4.00    --  105.88  77.00  90.00   43
 20  \w    126.00 171.00   1.00    4.00    --  105.88  77.00 150.00   45
 21  \w    113.00 172.00   1.00    4.00    --  105.88  77.00 120.00   59
 22  \w    111.00 172.00   1.00    4.00    --  105.88  77.00 -30.00   61
 23  \w    113.00 173.00   1.00    4.00    --  105.88  77.00-120.00   60
 24  \w     87.00 112.00   1.00    4.00    --  105.88  30.00 -90.00   25
 25  \w     85.00 111.00   1.00    4.00    --  105.88  30.00-120.00   26
 26  \w     84.00 116.00   1.00    4.00    --  105.88  30.00-150.00   32
 27  \w     88.00 113.00   1.00    4.00    --  105.88  61.00 -90.00   25
 28  \w     88.00 114.00   1.00    4.00    --  105.88  61.00 -60.00   26
 29  \w     88.00 113.00   1.00    4.00    --  105.88  61.00 -30.00   25
 30  \w     88.00 113.00   1.00    4.00    --  105.88  61.00   0.00   25
 31  \w     88.00 124.00   1.00    4.00    --  105.88  61.00  30.00   36
 32  \w     86.00 112.00   1.00    4.00    --  105.88  30.00  90.00   26
 33  \w     88.00 114.00   1.00    4.00    --  105.88  61.00  90.00   26
 34  \w     88.00 113.00   1.00    4.00    --  105.88  61.00 120.00   25
 35  \w     88.00 116.00   1.00    4.00    --  105.88  61.00 150.00   28
 36  \w     88.00 113.00   1.00    4.00    --  105.88  45.00 150.00   25
 37  \w     87.00 114.00   1.00    4.00    --  105.88  30.00 120.00   27
 38  \w     79.00 105.00   1.00    4.00    --  105.88  77.00 120.00   26
 39  \w     79.00 105.00   1.00    4.00    --  105.88  77.00  90.00   26
 40  \w     88.00 114.00   1.00    4.00    --  105.88  61.00  60.00   26
 41  \w     79.00 105.00   1.00    4.00    --  105.88  77.00   0.00   26
 42  \w     79.00 105.00   1.00    4.00    --  105.88  77.00 -30.00   26
 43  \w     79.00 105.00   1.00    4.00    --  105.88  77.00 -60.00   26
 44  \w     79.00 104.00   1.00    4.00    --  105.88  77.00 -90.00   25
 45  \w     79.00 104.00   1.00    4.00    --  105.88  77.00-120.00   25
 46  \w     79.00 109.00   1.00    4.00    --  105.88  77.00-150.00   30
 47  \w     88.00 113.00   1.00    4.00    --  105.88  61.00-180.00   25
 48  \w     79.00 105.00   1.00    4.00    --  105.88  77.00-180.00   26
 49  \w     85.00 111.00   1.00    4.00    --  105.88  30.00 -60.00   26
 50  \w     85.00 111.00   1.00    4.00    --  105.88  30.00   0.00   26
 51  \w     84.00 159.00   1.00    4.00    --  105.88  30.00  60.00   75
 52  \w     85.00 110.00   1.00    4.00    --  105.88  30.00 150.00   25
 53  \w     79.00 104.00   1.00    4.00    --  105.88  77.00 150.00   25
 54  \w     79.00 170.00   1.00    4.00    --  105.88  77.00  60.00   91
 55  \w     79.00 104.00   1.00    4.00    --  105.88  77.00  30.00   25
 56  \w     16.00  75.00   1.00    1.00    --   34.73  38.00 150.00   59
 57  \w      8.00  97.00   1.00    1.00    --   34.73  77.00 150.00   89
 58  \w     41.00 123.00   1.00    4.00    --  105.88 -77.00 -60.00   82
 59  \w     81.00 109.00   1.00    4.00    --  105.88 -94.00  30.00   28
 60  \w     67.00 103.00   1.00    1.00    --   34.73-161.00   6.00   36
 61  \w     38.00  87.00   1.00    1.00    --   34.73-125.00  30.00   49
 62  \w     38.00 108.00   1.00    4.00    --  105.88 -94.00 -90.00   70
 63  \w     47.00  85.00   1.00    1.00    --   34.73-125.00-180.00   38
 64  \w     39.00 103.00   1.00    4.00    --  105.88 -94.00-180.00   64
 65  \w     42.00  68.00   1.00    4.00    --  105.88 -94.00-120.00   26
 66  \w     41.00 109.00   1.00    4.00    --  105.88 -77.00  60.00   68
 67  \w    -33.00  -8.00   1.00    1.00    --  -34.73 -77.00-180.00   25
 68  \w    -33.00  50.00   1.00    1.00    --   34.73 -57.00-180.00   83
 69  \w    -32.00  50.00   1.00    1.00    --   34.73 -38.00   0.00   82
 70  \w    -31.00  50.00   1.00    1.00    --   34.73 -57.00  90.00   81
 71  \w   -100.00 -67.00   1.00    1.00    --  -34.73 -77.00-180.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0656912000
_diffrn_orient_matrix_UB_12      -0.0492423000
_diffrn_orient_matrix_UB_13      0.0944948000
_diffrn_orient_matrix_UB_21      0.0109692000
_diffrn_orient_matrix_UB_22      0.1306852000
_diffrn_orient_matrix_UB_23      0.0371209000
_diffrn_orient_matrix_UB_31      -0.1451559000
_diffrn_orient_matrix_UB_32      -0.0124254000
_diffrn_orient_matrix_UB_33      0.0151285000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21047
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.584
_diffrn_reflns_theta_max         66.584
_diffrn_reflns_theta_min         4.734
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0443P)^2^+0.6728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2698
_reflns_number_total             2911
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01711_si_001.cif
_cod_data_source_block           exp_904
_cod_database_code               4038846
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C200 H300 O8 N8 Cl8'
_shelx_estimated_absorpt_t_max   0.562
_shelx_estimated_absorpt_t_min   0.562
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C18(H18), C6(H6), C14(H14), C15(H15), C17(H17)
2.c X=CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              91390
_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 2.642
_oxdiff_exptl_absorpt_empirical_full_min 0.493