One-pot Nazarov cyclization/oxidative 1,2-carbon rearrangement/Ritter reaction to access 5-quaternary-4-amidocyclopent-2-enones and 2-quaternary-3-amidoindanones.
Hu, Yue-Hong; Chen, Yu-Ting; He, Zhi-Juan; Gan, Zhang-Yan; Zhang, Ling-Hui; Xi, Wen-Jie; Li, Baosheng; Zhang, Fu-Min; Chemical communications (Cambridge, England) 61 (2025) 3720–3723; doi:10.1039/d4cc06597b

data_1573796
_publ_section_title
;
 One-pot Nazarov cyclization/oxidative 1,2-carbon rearrangement/Ritter
 reaction to access 5-quaternary-4-amidocyclopent-2-enones and
 2-quaternary-3-amidoindanones.
;
_journal_issue                   18
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3720
_journal_page_last               3723
_journal_paper_doi               10.1039/d4cc06597b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C21 H21 N O2'
_chemical_formula_sum            'C21 H21 N O2'
_chemical_formula_weight         319.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-29
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-12-10 deposited with the CCDC.	2025-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.38050(10)
_cell_length_b                   17.9125(3)
_cell_length_c                   20.6371(3)
_cell_measurement_reflns_used    6642
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      75.8270
_cell_measurement_theta_min      5.3640
_cell_volume                     3467.61(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.957
_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    -28.00  22.00   0.50    0.80    --   46.32 -19.00 120.00  100
  2  \w     32.00  57.00   0.50    1.10    --  104.25 -61.00 120.00   50
  3  \w     48.00  73.00   0.50    1.10    --  104.25-127.00  57.00   50
  4  \w    -20.00  30.00   0.50    0.80    --   46.32  -7.00-120.00  100
  5  \w     76.00 113.00   0.50    1.10    --  104.25-127.00  57.00   74
  6  \w     36.00 111.00   0.50    1.10    --  104.25-125.00 147.00  150
  7  \w   -165.00-127.00   0.50    1.10    -- -102.00 -61.00-120.00   76
  8  \w   -174.00 -97.00   0.50    1.10    -- -102.00  -7.00-120.00  154
  9  \w    -85.00 -56.00   0.50    0.80    --  -46.32 125.00-134.00   58
 10  \w    -79.00 -34.00   0.50    1.10    -- -102.00 125.00 -30.00   90
 11  \w   -112.00 -86.00   0.50    1.10    -- -102.00 125.00  90.00   52
 12  \w    -78.00 -39.00   0.50    1.10    -- -102.00 125.00  90.00   78
 13  \w     -7.00  27.00   0.50    0.80    --  -46.32  19.00 -30.00   68
 14  \w    -69.00 -39.00   0.50    1.10    -- -102.00  61.00-180.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0128597000
_diffrn_orient_matrix_UB_12      -0.0852580000
_diffrn_orient_matrix_UB_13      0.0077405000
_diffrn_orient_matrix_UB_21      0.0083783000
_diffrn_orient_matrix_UB_22      -0.0093032000
_diffrn_orient_matrix_UB_23      -0.0741099000
_diffrn_orient_matrix_UB_31      0.1635504000
_diffrn_orient_matrix_UB_32      -0.0061992000
_diffrn_orient_matrix_UB_33      0.0044672000
_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  0.0307
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13330
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.081
_diffrn_reflns_theta_min         4.285
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0521P)^2^+1.0654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2991
_reflns_number_total             3472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06597b3.cif
_cod_data_source_block           huyuehong_0707_auto
_cod_depositor_comments
'Adding full bibliography for 1573796--1573800.cif.'
_cod_database_code               1573796
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 100.00
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C004(H004)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00J(H00L), C00K(H00M), C00M(H00Q), C00N(H00R), C00O(H00S)
2.c Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00H), C00I(H00I,H00J,H00K), C00L(H00N,H00O,H00P)
;
_shelx_res_checksum              81244
_shelx_hkl_checksum              23328
_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 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.764