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_7158547
_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_formula_moiety         'C21 H19 N O5'
_chemical_formula_sum            'C21 H19 N O5'
_chemical_formula_weight         365.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-10-23 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                   29.9557(10)
_cell_length_b                   7.3668(2)
_cell_length_c                   8.1504(3)
_cell_measurement_reflns_used    2771
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      73.3010
_cell_measurement_theta_min      2.9290
_cell_volume                     1798.61(10)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_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    -63.00  33.00   1.00    1.00    --  -40.73  38.00 150.00   96
  2  \w     48.00  74.00   1.00    1.00    --   40.73 -99.00 150.00   26
  3  \w     48.00 127.00   1.00    1.00    --  107.58 -61.00  30.00   79
  4  \w     95.00 131.00   1.00    1.00    --  107.58 -30.00 120.00   36
  5  \w     49.00 103.00   1.00    1.00    --  107.58 -95.00   0.00   54
  6  \w     19.00  59.00   1.00    1.00    --   40.73  38.00-150.00   40
  7  \w     89.00 173.00   1.00    1.00    --  107.58  45.00-180.00   84
;
_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      -0.0188726000
_diffrn_orient_matrix_UB_12      -0.1941046000
_diffrn_orient_matrix_UB_13      -0.0132699000
_diffrn_orient_matrix_UB_21      -0.0478818000
_diffrn_orient_matrix_UB_22      0.0762425000
_diffrn_orient_matrix_UB_23      0.0070591000
_diffrn_orient_matrix_UB_31      -0.0005589000
_diffrn_orient_matrix_UB_32      0.0164980000
_diffrn_orient_matrix_UB_33      -0.1882002000
_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  0.0246
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4152
_diffrn_reflns_point_group_measured_fraction_full 0.699
_diffrn_reflns_point_group_measured_fraction_max 0.668
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.424
_diffrn_reflns_theta_min         2.950
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51207
_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    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_coef       0.0026(2)
_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   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2419
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0322P)^2^+0.6986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.282
_reflns_Friedel_fraction_full    0.350
_reflns_Friedel_fraction_max     0.318
_reflns_number_gt                2218
_reflns_number_total             2419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02432a2.cif
_cod_data_source_block           g1
_cod_database_code               7158547
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8(4)
 0.2(4)
2. 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, All O(H) groups
3.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15),
 C16(H16), C17(H17)
3.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_shelx_res_checksum              79476
_shelx_hkl_checksum              81196
_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 1.543
_oxdiff_exptl_absorpt_empirical_full_min 0.539