Ring opening and skeletal reconstruction of 3-vinyl benzofuranone-chromone synthons: catalyst-free access to skeletally-diverse 2-pyridone and optically active imidazoline derivatives
Wang, Wei-Na; Liu, Ren-Ming; Zhang, Lei; Liu, Xiong-Li; Dai, Yi-Feng; Yu, Zhang-Biao; Peng, Li-Jun; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D1OB02432A

data_7158548
_publ_section_title
;
 Ring opening and skeletal reconstruction of 3-vinyl
 benzofuranone-chromone synthons: catalyst-free access to
 skeletally-diverse 2-pyridone and optically active imidazoline
 derivatives
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D1OB02432A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H30 N2 O3'
_chemical_formula_sum            'C35 H30 N2 O3'
_chemical_formula_weight         526.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-06
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-10-28 deposited with the CCDC.	2022-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.743(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5600(2)
_cell_length_b                   7.67541(19)
_cell_length_c                   16.0245(3)
_cell_measurement_reflns_used    13067
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      73.9210
_cell_measurement_theta_min      2.7970
_cell_volume                     1368.48(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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   -118.00  -9.00   1.00    1.00    --  -41.80 -77.00-150.00  109
  2  \w   -116.00 -17.00   1.00    1.00    --  -41.80 -38.00-120.00   99
  3  \w   -130.00  46.00   1.00    1.00    --  -41.80   0.00   0.00  176
  4  \w   -115.00 -14.00   1.00    1.00    --  -41.80 -57.00 120.00  101
  5  \w   -116.00 -17.00   1.00    1.00    --  -41.80 -38.00 120.00   99
  6  \w     23.00  98.00   1.00    1.00    --   41.80-125.00 -30.00   75
  7  \w     82.00 178.00   1.00    1.00    --  107.51  45.00-150.00   96
  8  \w     75.00 178.00   1.00    1.00    --  107.51  77.00 150.00  103
  9  \w     82.00 178.00   1.00    1.00    --  107.51  45.00 -90.00   96
 10  \w     76.00 103.00   1.00    1.00    --  107.51  77.00-120.00   27
 11  \w     82.00 111.00   1.00    1.00    --  107.51  45.00-120.00   29
 12  \w     75.00 102.00   1.00    1.00    --  107.51  77.00-180.00   27
 13  \w     45.00 103.00   1.00    1.00    --  107.51 -95.00-120.00   58
 14  \w     78.00 105.00   1.00    1.00    --  107.51  61.00-120.00   27
 15  \w    139.00 174.00   1.00    1.00    --  107.51  45.00 -60.00   35
 16  \w     78.00 105.00   1.00    1.00    --  107.51  61.00-150.00   27
 17  \w    118.00 171.00   1.00    1.00    --  107.51  61.00 -90.00   53
 18  \w    137.00 170.00   1.00    1.00    --  107.51  61.00-120.00   33
 19  \w     80.00 107.00   1.00    1.00    --  107.51  61.00-180.00   27
 20  \w     75.00 102.00   1.00    1.00    --  107.51  77.00 120.00   27
 21  \w     85.00 112.00   1.00    1.00    --  107.51  45.00 -60.00   27
 22  \w     79.00 111.00   1.00    1.00    --  107.51  61.00 -90.00   32
 23  \w     80.00 106.00   1.00    1.00    --  107.51  61.00 120.00   26
 24  \w     83.00 178.00   1.00    1.00    --  107.51  45.00-180.00   95
 25  \w     78.00 108.00   1.00    1.00    --  107.51  61.00 150.00   30
 26  \w     75.00 101.00   1.00    1.00    --  107.51  77.00-150.00   26
 27  \w     84.00 111.00   1.00    1.00    --  107.51  45.00 150.00   27
 28  \w     85.00 112.00   1.00    1.00    --  107.51  30.00-180.00   27
 29  \w     32.00 135.00   1.00    1.00    --  107.51 -30.00 120.00  103
 30  \w    148.00 173.00   1.00    1.00    --  107.51  61.00 120.00   25
 31  \w     25.00 104.00   1.00    1.00    --  107.51 -95.00 -60.00   79
 32  \w     28.00  54.00   1.00    1.00    --   41.67  38.00 -30.00   26
 33  \w     82.00 108.00   1.00    1.00    --  107.51  45.00-180.00   26
 34  \w    153.00 178.00   1.00    1.00    --  107.51 125.00 -30.00   25
 35  \w    153.00 178.00   1.00    1.00    --  107.51  45.00   0.00   25
 36  \w    -66.00   9.00   1.00    1.00    --  -41.67  38.00 -90.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0645306000
_diffrn_orient_matrix_UB_12      0.0360522000
_diffrn_orient_matrix_UB_13      0.0959326000
_diffrn_orient_matrix_UB_21      -0.1224124000
_diffrn_orient_matrix_UB_22      0.0283406000
_diffrn_orient_matrix_UB_23      0.0189314000
_diffrn_orient_matrix_UB_31      -0.0058603000
_diffrn_orient_matrix_UB_32      -0.1953298000
_diffrn_orient_matrix_UB_33      0.0204175000
_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  0.0253
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16343
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.091
_diffrn_reflns_theta_min         2.865
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 2097 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(9)
_refine_ls_extinction_coef       0.0138(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5186
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0531P)^2^+0.1006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.895
_reflns_Friedel_fraction_max     0.859
_reflns_number_gt                5080
_reflns_number_total             5186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02432a2.cif
_cod_data_source_block           g3
_cod_database_code               7158548
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H26 N26 O26 '
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C22(H22), C23(H23)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C12(H12), C14(H14), C17(H17), C18(H18), C19(H19),
 C20(H20), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32),
  C33(H33), C34(H34), C35(H35)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_shelx_res_checksum              12215
_shelx_hkl_checksum              54212
_olex2_date_sample_data_collection 2021-10-06
_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 1.458
_oxdiff_exptl_absorpt_empirical_full_min 0.564