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_7157166
_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 H18 Br N O3'
_chemical_formula_sum            'C25 H18 Br N O3'
_chemical_formula_weight         460.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-08-02 deposited with the CCDC.    2019-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.7340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2679(7)
_cell_length_b                   11.9073(8)
_cell_length_c                   18.5390(13)
_cell_measurement_reflns_used    5501
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.81
_cell_measurement_theta_min      2.25
_cell_volume                     1995.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22109
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.084
_diffrn_reflns_theta_min         2.048
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.160
_exptl_transmission_factor_max   0.2134
_exptl_transmission_factor_min   0.1541
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0533P)^2^+0.4724P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.1022
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4577
_reflns_number_total             5922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02193k2.cif
_cod_data_source_block           mo_gd_lxl32_0m
_cod_database_code               7157166
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.481
_shelx_estimated_absorpt_t_max   0.731
_shelx_res_checksum              5157
_shelx_hkl_checksum              24834