Thermal-mediated [1,3]-hydrogen transfer as the key step: access to oxindole-chromone hybrid collection with structural diversity
Gong, Ying; Xu, Sheng-Wen; Liu, Xiong-Wei; Li, Zheng; Liu, Xiong-Li; Yao, Zhen; Zhou, Ying; Organic & Biomolecular Chemistry  (2019) –; doi:10.1039/C9OB02193K

data_7157171
_publ_section_title
;
 Thermal-mediated [1,3]-hydrogen transfer as the key step: access to
 oxindole-chromone hybrid collection with structural diversity
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C9OB02193K
_journal_year                    2019
_chemical_formula_moiety         'C25 H17 Cl N O4, C H4 O'
_chemical_formula_sum            'C26 H21 Cl N O5'
_chemical_formula_weight         462.89
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-05-16 deposited with the CCDC.    2019-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                92.396(4)
_cell_angle_beta                 100.320(5)
_cell_angle_gamma                101.272(5)
_cell_formula_units_Z            2
_cell_length_a                   9.1764(6)
_cell_length_b                   10.3922(5)
_cell_length_c                   11.8331(7)
_cell_measurement_reflns_used    3636
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.1600
_cell_measurement_theta_min      3.7340
_cell_volume                     1085.31(11)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.964
_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    -59.00  32.00   1.00    1.00    --  -40.98  57.00 150.00   91
  2  \w    -95.00 -26.00   1.00    1.00    --  -40.98 -37.00 -90.00   69
  3  \w     54.00  97.00   1.00    1.00    --   40.98-125.00 -30.00   43
  4  \w     43.00  70.00   1.00    1.00    --  106.95 -61.00-150.00   27
  5  \w     58.00  92.00   1.00    1.00    --  106.95 -94.00-180.00   34
  6  \w     95.00 128.00   1.00    1.00    --  106.95 -61.00-150.00   33
  7  \w    115.00 166.00   1.00    1.00    --  106.95  30.00-180.00   51
  8  \w     56.00 107.00   1.00    1.00    --  106.95 -94.00   0.00   51
  9  \w     44.00  95.00   1.00    1.00    --  106.95-125.00 -90.00   51
 10  \w     35.00 131.00   1.00    1.00    --  106.95 -45.00 -60.00   96
 11  \w     42.00 108.00   1.00    1.00    --  106.95 -94.00  90.00   66
 12  \w     40.00 128.00   1.00    1.00    --  106.95 -45.00  60.00   88
 13  \w     79.00 106.00   1.00    1.00    --  106.95  30.00 120.00   27
 14  \w    136.00 176.00   1.00    1.00    --  106.95  30.00 120.00   40
 15  \w     39.00 120.00   1.00    1.00    --  106.95-125.00 -30.00   81
 16  \w     27.00 143.00   1.00    1.00    --  106.95 -15.00 150.00  116
 17  \w    -67.00  -3.00   1.00    1.00    --  -40.98 125.00-180.00   64
 18  \w   -115.00 -17.00   1.00    1.00    --  -40.98 -37.00   0.00   98
;
_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      -0.1506912000
_diffrn_orient_matrix_UB_12      0.0163291000
_diffrn_orient_matrix_UB_13      -0.0736852000
_diffrn_orient_matrix_UB_21      -0.0199477000
_diffrn_orient_matrix_UB_22      0.0971221000
_diffrn_orient_matrix_UB_23      0.0952390000
_diffrn_orient_matrix_UB_31      0.0854981000
_diffrn_orient_matrix_UB_32      0.1153053000
_diffrn_orient_matrix_UB_33      -0.0558864000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7160
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.418
_diffrn_reflns_theta_min         3.809
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.895
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53211
_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    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             482
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0599
_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^)+(0.1014P)^2^+0.5684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1747
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3658
_reflns_number_total             4207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02193k2.cif
_cod_data_source_block           exp_963
_cod_database_code               7157171
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.805
_shelx_estimated_absorpt_t_min   0.764
_reflns_odcompleteness_completeness 99.66
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C5(H5), C2(H2), C24(H24), C4(H4), C16(H16), C7(H7), C13(H13),
 C22(H22), C21(H21), C19(H19), C15(H15), C20(H20), C14(H14)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O3(H3)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.927
_oxdiff_exptl_absorpt_empirical_full_min 0.677