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_7158549
_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         'C33 H26 N2 O3'
_chemical_formula_sum            'C33 H26 N2 O3'
_chemical_formula_weight         498.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-11
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-10-28 deposited with the CCDC.	2022-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.58570(10)
_cell_length_b                   11.06500(10)
_cell_length_c                   26.4839(2)
_cell_measurement_reflns_used    24244
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      73.7200
_cell_measurement_theta_min      3.3100
_cell_volume                     2515.99(4)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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   -129.00  47.00   1.00    1.00    --  -40.73   0.00 -90.00  176
  2  \w     23.00  97.00   1.00    1.00    --   40.73-125.00-150.00   74
  3  \w     94.00 178.00   1.00    1.22    --  107.58 125.00 120.00   84
  4  \w     25.00 110.00   1.00    1.22    --  107.58 -95.00  30.00   85
  5  \w     25.00 110.00   1.00    1.22    --  107.58 -95.00-150.00   85
  6  \w     25.00 110.00   1.00    1.22    --  107.58 -95.00  60.00   85
  7  \w     79.00 178.00   1.00    1.22    --  107.58  30.00 -90.00   99
  8  \w     34.00 122.00   1.00    1.22    --  107.58-125.00 150.00   88
  9  \w     25.00 110.00   1.00    1.22    --  107.58 -95.00 150.00   85
 10  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00-180.00  109
 11  \w    -34.00  65.00   1.00    1.00    --   40.73 -38.00   0.00   99
 12  \w      8.00 117.00   1.00    1.00    --   40.73  77.00  90.00  109
 13  \w     79.00 178.00   1.00    1.22    --  107.58  30.00-180.00   99
 14  \w     79.00 178.00   1.00    1.22    --  107.58  30.00   0.00   99
 15  \w     35.00 133.00   1.00    1.22    --  107.58 -45.00-180.00   98
 16  \w     78.00 178.00   1.00    1.22    --  107.58  61.00-150.00  100
 17  \w     78.00 178.00   1.00    1.22    --  107.58  61.00 -60.00  100
 18  \w     79.00 178.00   1.00    1.22    --  107.58  30.00  90.00   99
 19  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00 -60.00  109
 20  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00  30.00  109
 21  \w     23.00  97.00   1.00    1.00    --   40.73-125.00 -30.00   74
 22  \w     82.00 174.00   1.00    1.22    --  107.58  45.00  30.00   92
 23  \w     75.00 178.00   1.00    1.22    --  107.58  77.00  90.00  103
;
_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      0.0362718000
_diffrn_orient_matrix_UB_12      0.1044509000
_diffrn_orient_matrix_UB_13      -0.0366335000
_diffrn_orient_matrix_UB_21      0.1012222000
_diffrn_orient_matrix_UB_22      -0.0856003000
_diffrn_orient_matrix_UB_23      -0.0320688000
_diffrn_orient_matrix_UB_31      -0.1436161000
_diffrn_orient_matrix_UB_32      -0.0339102000
_diffrn_orient_matrix_UB_33      -0.0318407000
_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  0.0432
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            34007
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.877
_diffrn_reflns_theta_min         3.338
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07140
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 2109 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_coef       0.0028(3)
_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   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0285
_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^)+(0.0456P)^2^+0.2352P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0764
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4978
_reflns_number_total             5079
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02432a2.cif
_cod_data_source_block           68
_cod_database_code               7158549
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.912
_reflns_odcompleteness_completeness 99.96
_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:
 C19(H19), C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C9(H9), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29),
  C30(H30), C31(H31), C32(H32)
2.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_shelx_res_checksum              86223
_shelx_hkl_checksum              83382
_olex2_date_sample_data_collection 2021-10-10
_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 8.150
_oxdiff_exptl_absorpt_empirical_full_min 0.519