2-Imidazolidinone benzofurans as unexpected outcome of the Lewis acid mediated Nenitzescu reaction
Horsten, Tomas; Alegbejo Price, Temitayo Omowumi; Van Meervelt, Luc; Emery, Flavio da Silva; Dehaen, Wim; New Journal of Chemistry 46 (2022) 2028–2032; doi:10.1039/D1NJ04965H

data_7061185
_publ_section_title
;
 2-Imidazolidinone benzofurans as unexpected outcome of the Lewis acid
 mediated Nenitzescu reaction
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2028
_journal_page_last               2032
_journal_paper_doi               10.1039/D1NJ04965H
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C14 H14 N2 O5'
_chemical_formula_sum            'C14 H14 N2 O5'
_chemical_formula_weight         290.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-02 deposited with the CCDC.	2022-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                66.339(5)
_cell_angle_beta                 84.385(4)
_cell_angle_gamma                81.355(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4320(3)
_cell_length_b                   8.6450(5)
_cell_length_c                   10.0078(5)
_cell_measurement_reflns_used    6051
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8580
_cell_measurement_theta_min      3.2370
_cell_volume                     660.03(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_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    -20.00  25.00   1.00    2.50    --  -17.15 -99.00 -30.00   45
  2  \w    -20.00  25.00   1.00    2.50    --  -17.15 -99.00-150.00   45
  3  \w     -3.00  88.00   1.00    2.50    --   18.87  57.00 -60.00   91
  4  \w     35.00  95.00   1.00    2.50    --   18.87 178.00  60.00   60
  5  \w    -52.00  41.00   1.00    2.50    --   18.87 -48.00  42.00   93
  6  \w     -7.00  91.00   1.00    2.50    --   18.87  38.00-150.00   98
  7  \w    -93.00 -35.00   1.00    2.50    --  -17.15-178.00  90.00   58
  8  \w    -50.00  40.00   1.00    2.50    --   18.87 -57.00 150.00   90
  9  \w    -20.00  61.00   1.00    2.50    --   18.87 -99.00 -90.00   81
 10  \w    -20.00  61.00   1.00    2.50    --   18.87 -99.00  90.00   81
 11  \w     -7.00  91.00   1.00    2.50    --   18.87  38.00  90.00   98
 12  \w    -86.00   4.00   1.00    2.50    --  -17.15 -57.00  90.00   90
 13  \w    -20.00   5.00   1.00    2.50    --  -17.15 -99.00 -60.00   25
 14  \w    -20.00  61.00   1.00    2.50    --   18.87 -99.00 -30.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0136832000
_diffrn_orient_matrix_UB_12      -0.0709515000
_diffrn_orient_matrix_UB_13      -0.0200866000
_diffrn_orient_matrix_UB_21      -0.0703722000
_diffrn_orient_matrix_UB_22      -0.0308442000
_diffrn_orient_matrix_UB_23      0.0408857000
_diffrn_orient_matrix_UB_31      -0.0459647000
_diffrn_orient_matrix_UB_32      0.0464708000
_diffrn_orient_matrix_UB_33      -0.0626313000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0198
_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       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13643
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.445
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
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    1.461
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.040(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0407P)^2^+0.2227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1039
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2225
_reflns_number_total             2698
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj04965h2.cif
_cod_data_source_block           wdh1105
_cod_depositor_comments          'Adding full bibliography for 7061185.cif.'
_cod_database_code               7061185
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C14 H14 N2 O4'
_chemical_oxdiff_usercomment     TH-627
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.956
_diffrn_oxdiff_ac4_digest_frames
;
0117c9070dc35bfc9dbd54ea9991d56065000280503
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C13(H13A,H13B), C14(H14A,H14B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              35574
_olex2_submission_original_sample_id TH-627
_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 1.566
_oxdiff_exptl_absorpt_empirical_full_min 0.650