Lewis base promoted [4 + 2] annulation of <i>o</i>-acylamino-aryl MBH carbonates with isatin.
Shen, Li-Wen; Luo, Nian; Jia, Yun-Qing; Wang, Guang-Wei; Yuan, Shu-Pei; Xiang, Min; Organic & biomolecular chemistry 22 (2024) 7961–7964; doi:10.1039/d4ob01240b

data_7160133
_publ_section_title
;
 Lewis base promoted [4 + 2] annulation of <i>o</i>-acylamino-aryl MBH
 carbonates with isatin.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7961
_journal_page_last               7964
_journal_paper_doi               10.1039/d4ob01240b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C26 H28 N2 O6'
_chemical_formula_sum            'C26 H28 N2 O6'
_chemical_formula_weight         464.50
_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
_audit_creation_date             2024-05-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-06-05 deposited with the CCDC.	2024-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.953(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2639(3)
_cell_length_b                   23.4915(6)
_cell_length_c                   13.1699(4)
_cell_measurement_reflns_used    3957
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9840
_cell_measurement_theta_min      3.7540
_cell_volume                     2458.23(14)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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      2.00  33.00   1.00    1.10    --  -33.50  57.00   0.00   31
  2  \w    -73.00 -35.00   1.00    1.10    --  -33.50 178.00-120.00   38
  3  \w    -41.00 -11.00   1.00    1.10    --  -33.50 -37.00-150.00   30
  4  \w    -99.00 -73.00   1.00    1.10    --  -33.50 -37.00-150.00   26
  5  \w     61.00  87.00   1.00    1.10    --   36.47 178.00 -90.00   26
  6  \w    -10.00  46.00   1.00    1.10    --   36.47 -77.00 -90.00   56
  7  \w     64.00  90.00   1.00    1.10    --   36.47  57.00  30.00   26
  8  \w     63.00 103.00   1.00    1.10    --   36.47  57.00 150.00   40
  9  \w     27.00  53.00   1.00    1.10    --   36.47  57.00 150.00   26
 10  \w    -35.00  57.00   1.00    1.10    --   36.47 -19.00  30.00   92
 11  \w     19.00  52.00   1.00    1.10    --   36.47  57.00  30.00   33
 12  \w     44.00 125.00   1.00    5.50    --  108.00 -61.00  60.00   81
 13  \w     83.00 170.00   1.00    5.50    --  108.00  30.00 -60.00   87
 14  \w    103.00 158.00   1.00    5.50    --  108.00  77.00 150.00   55
 15  \w     86.00 128.00   1.00    5.50    --  108.00 -45.00 -60.00   42
 16  \w     40.00  65.00   1.00    5.50    --  108.00 -45.00 -60.00   25
 17  \w     40.00  98.00   1.00    5.50    --  108.00-111.00 -30.00   58
 18  \w    121.00 152.00   1.00    5.50    --  108.00 111.00 150.00   31
 19  \w     44.00 101.00   1.00    5.50    --  108.00 -77.00  30.00   57
 20  \w     62.00 136.00   1.00    5.50    --  108.00 178.00 -30.00   74
;
_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      -0.1831588000
_diffrn_orient_matrix_UB_12      0.0093898000
_diffrn_orient_matrix_UB_13      0.0030278000
_diffrn_orient_matrix_UB_21      0.0327779000
_diffrn_orient_matrix_UB_22      -0.0366823000
_diffrn_orient_matrix_UB_23      0.1006263000
_diffrn_orient_matrix_UB_31      0.0545529000
_diffrn_orient_matrix_UB_32      0.0535017000
_diffrn_orient_matrix_UB_33      0.0683796000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9520
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         3.763
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
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    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4370
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0585
_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^)+(0.0933P)^2^+0.4004P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1695
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3455
_reflns_number_total             4370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01240b2.cif
_cod_data_source_block           202405181
_cod_depositor_comments          'Adding full bibliography for 7160133.cif.'
_cod_original_cell_volume        2458.23(13)
_cod_database_code               7160133
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N3O1
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.904
_reflns_odcompleteness_completeness 99.54
_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. Restrained distances
 C11-C12
 1.54 with sigma of 0.02
 O2-C11
 1.43 with sigma of 0.02
 O2-C11A
 1.43 with sigma of 0.02
 C11A-C12A
 1.54 with sigma of 0.02
3. Rigid bond restraints
 O2, C9
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C11) = Uanis(C11A)
Uanis(C12) = Uanis(C12A)
5. Others
 Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C7(H7)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C11A(H11C,H11D)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C22(H22), C23(H23), C24(H24), C25(H25)
6.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
6.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C12A(H12D,H12E,H12F), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              63917
_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 1.186
_oxdiff_exptl_absorpt_empirical_full_min 0.924