3-Vinyl oxindole-chromone synthon as a skeletal reconstruction reactant for the synthesis of 2-hydroxy benzoyl pyridones
Zhang, Lei; Liu, Ren-Ming; Wang, Wei-Na; Liu, Xiong-Li; Dai, Yi-Feng; Yu, Zhang-Biao; Peng, Li-Jun; New Journal of Chemistry 46 (2022) 5474–5478; doi:10.1039/D1NJ06112G

data_7061388
_publ_section_title
;
 3-Vinyl oxindole-chromone synthon as a skeletal reconstruction reactant
 for the synthesis of 2-hydroxy benzoyl pyridones
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5474
_journal_page_last               5478
_journal_paper_doi               10.1039/D1NJ06112G
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C24 H24 N2 O6'
_chemical_formula_sum            'C24 H24 N2 O6'
_chemical_formula_weight         436.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-05
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-12-18 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.796(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3858(3)
_cell_length_b                   25.0398(5)
_cell_length_c                   9.6706(2)
_cell_measurement_reflns_used    5093
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      74.1070
_cell_measurement_theta_min      3.4600
_cell_volume                     2138.46(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-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      149.99(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 0.972
_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  78.00   1.00    1.00    --   40.73 -99.00  90.00   76
  2  \w     40.00  97.00   1.00    1.00    --  108.20-125.00  90.00   57
  3  \w     90.00 120.00   1.00    1.00    --  108.20-125.00   0.00   30
  4  \w     47.00 131.00   1.00    1.00    --  108.20 -45.00  60.00   84
  5  \w    143.00 176.00   1.00    1.00    --  108.20  45.00 150.00   33
  6  \w    132.00 167.00   1.00    1.00    --  108.20  45.00   0.00   35
  7  \w    131.00 177.00   1.00    1.00    --  108.20  45.00-120.00   46
  8  \w     83.00 117.00   1.00    1.00    --  108.20  45.00   0.00   34
  9  \w     87.00 114.00   1.00    1.00    --  108.20  45.00 150.00   27
 10  \w     36.00 139.00   1.00    1.00    --  108.20 -77.00-150.00  103
 11  \w     28.00  68.00   1.00    1.00    --   40.73  38.00-180.00   40
 12  \w   -117.00 -11.00   1.00    1.00    --  -40.73 -77.00-150.00  106
;
_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      0.1046590000
_diffrn_orient_matrix_UB_12      0.0299859000
_diffrn_orient_matrix_UB_13      0.1354054000
_diffrn_orient_matrix_UB_21      0.0428936000
_diffrn_orient_matrix_UB_22      -0.0533175000
_diffrn_orient_matrix_UB_23      0.0833381000
_diffrn_orient_matrix_UB_31      0.1327893000
_diffrn_orient_matrix_UB_32      -0.0064848000
_diffrn_orient_matrix_UB_33      -0.0583066000
_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  0.0203
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8412
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.285
_diffrn_reflns_theta_min         3.530
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84332
_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    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0458P)^2^+0.7623P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3842
_reflns_number_total             4239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj06112g2.cif
_cod_data_source_block           a-13_4
_cod_depositor_comments
'Adding full bibliography for 7061387--7061388.cif.'
_cod_database_code               7061388
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.895
_reflns_odcompleteness_completeness 99.87
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2A), C2(H2B), C4(H4), C5(H5), C9(H9), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              32978
_olex2_date_sample_data_collection 2021-07-05
_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 1.301
_oxdiff_exptl_absorpt_empirical_full_min 0.722