Iodine(iii) promoted ring-rearrangement reaction of 1-arylamino-2-oxocyclopentane-1-carbonitriles to synthesize N-aryl-δ-valerolactams.
Bhattacherjee, Dhananjay; Shaifali, ?; Kumar, Ajay; Sharma, Ajay; Purohit, Rituraj; Das, Pralay; Organic & biomolecular chemistry 18 (2020) 745–749; doi:10.1039/c9ob02598g

data_7157264
_publ_section_title
;
 Iodine(iii) promoted ring-rearrangement reaction of
 1-arylamino-2-oxocyclopentane-1-carbonitriles to synthesize
 N-aryl-\d-valerolactams.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              745
_journal_page_last               749
_journal_paper_doi               10.1039/c9ob02598g
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C15 H13 N3 O'
_chemical_formula_sum            'C15 H13 N3 O'
_chemical_formula_weight         251.28
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-08-28
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_audit_update_record
;
2018-08-09 deposited with the CCDC.	2019-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.209(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5028(10)
_cell_length_b                   10.3065(10)
_cell_length_c                   17.339(2)
_cell_measurement_reflns_used    1369
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.9090
_cell_measurement_theta_min      4.9880
_cell_volume                     1338.7(3)
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_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    -53.00 -24.00   1.00    1.00    --   25.57 -77.00  60.00   29
  2  \w    -22.00  30.00   1.00    1.00    --   25.57 -77.00  60.00   52
  3  \w     35.00  68.00   1.00    1.00    --   25.57 -77.00  60.00   33
  4  \w     27.00 103.00   1.00    2.15    --  108.00-104.00 -30.00   76
  5  \w     96.00 156.00   1.00    2.15    --  108.00 -89.00  30.00   60
  6  \w     68.00 141.00   1.00    2.15    --  108.00  54.00   0.00   73
  7  \w    149.00 174.00   1.00    2.15    --  108.00  54.00 -30.00   25
  8  \w    100.00 139.00   1.00    1.00    --   66.78 111.00-180.00   39
  9  \w     60.00 139.00   1.00    1.00    --   66.78 178.00 -60.00   79
 10  \w     85.00 135.00   1.00    2.15    --  108.00  54.00 -30.00   50
 11  \w     89.00 144.00   1.00    1.00    --   66.78 141.00 138.00   55
 12  \w      2.00  98.00   1.00    1.00    --   25.57  57.00-180.00   96
 13  \w     29.00 140.00   1.00    2.15    --  108.00  21.00-180.00  111
 14  \w     31.00 113.00   1.00    2.15    --  108.00-104.00-150.00   82
 15  \w     23.00  65.00   1.00    2.15    --  108.00-104.00 -60.00   42
 16  \w     23.00  79.00   1.00    2.15    --  108.00 -89.00  30.00   56
 17  \w    -16.00  84.00   1.00    1.00    --   66.78 -77.00-120.00  100
 18  \w     -1.00 136.00   1.00    1.00    --   66.78  30.00-180.00  137
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1677733000
_diffrn_orient_matrix_UB_12      0.0454743000
_diffrn_orient_matrix_UB_13      -0.0398419000
_diffrn_orient_matrix_UB_21      0.0584639000
_diffrn_orient_matrix_UB_22      -0.1421509000
_diffrn_orient_matrix_UB_23      -0.0091911000
_diffrn_orient_matrix_UB_31      -0.1036954000
_diffrn_orient_matrix_UB_32      -0.0065122000
_diffrn_orient_matrix_UB_33      -0.0790496000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3969
_diffrn_reflns_theta_full        66.93
_diffrn_reflns_theta_max         66.93
_diffrn_reflns_theta_min         4.99
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.453
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.333
_exptl_crystal_size_min          0.141
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.639
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.639
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.0934
_refine_ls_shift/su_max          0.111
_refine_ls_shift/su_mean         0.015
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2885
_refine_ls_wR_factor_ref         0.4097
_reflns_number_gt                1466
_reflns_number_total             2259
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob02598g2.cif
_cod_data_source_block           3i_rt_cu
_cod_depositor_comments          'Adding full bibliography for 7157264.cif.'
_cod_database_code               7157264
_chemical_oxdiff_formula         'C60 H52 N12 O4'
_reflns_odcompleteness_completeness 94.40
_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.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C12(H12), C5(H5), C11(H11)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
;
_olex2_date_sample_data_collection 2017-08-24
_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 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.762