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_7061387
_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 H23 Cl N2 O6'
_chemical_formula_sum            'C24 H23 Cl N2 O6'
_chemical_formula_weight         470.89
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-07-16
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-10-23 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                92.200(7)
_cell_angle_beta                 101.856(7)
_cell_angle_gamma                108.128(6)
_cell_formula_units_Z            2
_cell_length_a                   7.0463(4)
_cell_length_b                   10.8325(7)
_cell_length_c                   15.8212(15)
_cell_measurement_reflns_used    2952
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.6550
_cell_measurement_theta_min      2.2830
_cell_volume                     1116.38(15)
_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    'SHELXS  (Sheldrick, 2008)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -77.00  18.00   1.00    3.00    --  -11.27 -77.00   0.00   95
  2  \w    -54.00  36.00   1.00    3.00    --   11.90 -57.00 120.00   90
  3  \w    -14.00  85.00   1.00    3.00    --   11.90  57.00 -90.00   99
;
_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      -0.0408154000
_diffrn_orient_matrix_UB_12      -0.0323143000
_diffrn_orient_matrix_UB_13      -0.0428104000
_diffrn_orient_matrix_UB_21      0.0522835000
_diffrn_orient_matrix_UB_22      0.0574110000
_diffrn_orient_matrix_UB_23      -0.0167674000
_diffrn_orient_matrix_UB_31      0.0862554000
_diffrn_orient_matrix_UB_32      -0.0215636000
_diffrn_orient_matrix_UB_33      0.0032153000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.1305
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3934
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.990
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47585
_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    1.401
_exptl_crystal_description       prism
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0883
_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^)+(0.0722P)^2^+5.3105P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2324
_refine_ls_wR_factor_ref         0.2447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3000
_reflns_number_total             3934
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj06112g2.cif
_cod_data_source_block           a-28
_cod_depositor_comments
'Adding full bibliography for 7061387--7061388.cif.'
_cod_database_code               7061387
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.690(7)
 0.310(7)
2. 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
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), N2(H2), C3(H3), C4(H4), C6(H6), C9(H9), C10(H10), C14(H14), C16(H16),
  C17(H17)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              94543
_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 1.646
_oxdiff_exptl_absorpt_empirical_full_min 0.578