Silver-catalyzed cascade cyclization and functionalization of N-aryl-4-pentenamides: an efficient route to γ-lactam-substituted quinone derivatives
Fang, Zeguo; Xie, Lin; Wang, Liang; Zhang, Qian; Li, Dong; RSC Advances 12 (2022) 26776–26780; doi:10.1039/D2RA05283K

data_7245518
_publ_section_title
;
 Silver-catalyzed cascade cyclization and functionalization of
 N-aryl-4-pentenamides: an efficient route to \g-lactam-substituted
 quinone derivatives
;
_journal_issue                   41
_journal_name_full               'RSC Advances'
_journal_page_first              26776
_journal_page_last               26780
_journal_paper_doi               10.1039/D2RA05283K
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C21 H16 Cl N O3'
_chemical_formula_sum            'C21 H16 Cl N O3'
_chemical_formula_weight         365.80
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-06 deposited with the CCDC.	2022-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.9190(3)
_cell_length_b                   24.1190(8)
_cell_length_c                   16.1511(5)
_cell_measurement_reflns_used    4397
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4270
_cell_measurement_theta_min      5.2830
_cell_volume                     3474.4(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    '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 0.999
_diffrn_measured_fraction_theta_max 0.983
_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   -108.00 -38.00   1.00    3.00    --  -33.50 178.00 150.00   70
  2  \w     78.00 104.00   1.00    3.00    --   36.47 178.00-180.00   26
  3  \w     11.00  58.00   1.00    3.00    --   36.47 -99.00-180.00   47
  4  \w     11.00  40.00   1.00    3.00    --   36.47 -37.00 120.00   29
  5  \w    -24.00   2.00   1.00    3.00    --   36.47 -37.00 120.00   26
  6  \w     18.00 104.00   1.00    3.00    --   36.47  57.00 120.00   86
  7  \w     49.00 124.00   1.00   12.50    --  108.00 -45.00  90.00   75
  8  \w     92.00 167.00   1.00   12.50    --  108.00  61.00 -90.00   75
  9  \w     40.00 134.00   1.00   12.50    --  108.00 -77.00 -30.00   94
 10  \w     54.00  86.00   1.00   12.50    --  108.00 -94.00-180.00   32
 11  \w    136.00 162.00   1.00   12.50    --  108.00  61.00  30.00   26
 12  \w     62.00 100.00   1.00    3.00    --   36.47 178.00 -60.00   38
 13  \w    -29.00  20.00   1.00    3.00    --   36.47 -77.00 150.00   49
 14  \w     64.00 103.00   1.00    3.00    --   36.47 178.00 150.00   39
 15  \w     52.00  86.00   1.00    3.00    --   36.47  77.00 150.00   34
 16  \w     64.00 147.00   1.00   12.50    --  108.00 178.00   0.00   83
 17  \w     88.00 132.00   1.00   12.50    --  108.00  45.00  60.00   44
 18  \w     47.00  89.00   1.00   12.50    --  108.00 -94.00 -60.00   42
 19  \w    115.00 145.00   1.00   12.50    --  108.00  61.00-150.00   30
;
_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      0.1382361000
_diffrn_orient_matrix_UB_12      0.0364867000
_diffrn_orient_matrix_UB_13      -0.0175061000
_diffrn_orient_matrix_UB_21      0.0874130000
_diffrn_orient_matrix_UB_22      -0.0515232000
_diffrn_orient_matrix_UB_23      -0.0291167000
_diffrn_orient_matrix_UB_31      -0.0555981000
_diffrn_orient_matrix_UB_32      0.0096705000
_diffrn_orient_matrix_UB_33      -0.0891224000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13535
_diffrn_reflns_point_group_measured_fraction_full 0.803
_diffrn_reflns_point_group_measured_fraction_max 0.783
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.142
_diffrn_reflns_theta_min         3.665
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94991
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1329 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         5271
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0549P)^2^+0.3380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.531
_reflns_Friedel_fraction_full    0.590
_reflns_Friedel_fraction_max     0.565
_reflns_number_gt                4602
_reflns_number_total             5271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra05283k2.cif
_cod_data_source_block           20220330
_cod_original_cell_volume        3474.39(19)
_cod_database_code               7245518
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N2Br1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.816
_shelx_estimated_absorpt_t_min   0.741
_reflns_odcompleteness_completeness 99.92
_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
2.a Ternary CH refined with riding coordinates:
 C10(H10), C10'(H10')
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C8'(H8'A,H8'B), C9'(H9'A,H9'B),
 C11'(H11C,H11D)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C18(H18), C19(H19), C20(H20),
 C21(H21), C2'(H2'), C3'(H3'), C4'(H4'), C5'(H5'), C6'(H6'), C18'(H18'),
 C19'(H19'), C20'(H20'), C21'(H21')
;
_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 1.124
_oxdiff_exptl_absorpt_empirical_full_min 0.918