Pd(II)-catalyzed domino C-H addition/Heck reaction for stereoselective 3-alkylideneoxindole synthesis.
Hong, Kai; Zhang, Tengfei; Li, Qing; Li, Xue; Sun, Zhonghui; Zhao, Gongyuan; Peng, Jinsong; Chen, Chunxia; Organic & biomolecular chemistry 23 (2025) 6391–6399; doi:10.1039/d5ob00666j

data_7160582
_publ_section_title
;
 Pd(II)-catalyzed domino C-H addition/Heck reaction for stereoselective
 3-alkylideneoxindole synthesis.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6391
_journal_page_last               6399
_journal_paper_doi               10.1039/d5ob00666j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C20 H17 N O3'
_chemical_formula_sum            'C20 H17 N O3'
_chemical_formula_weight         319.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-07-09
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-11 deposited with the CCDC.	2025-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.404(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.883(4)
_cell_length_b                   6.841(2)
_cell_length_c                   22.542(7)
_cell_measurement_reflns_used    7023
_cell_measurement_temperature    200.00
_cell_measurement_theta_max      54.462
_cell_measurement_theta_min      3.582
_cell_volume                     1655.7(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      200.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0988
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19145
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        52.978
_diffrn_reflns_theta_max         52.978
_diffrn_reflns_theta_min         3.581
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1384 before and 0.0734 after correction.
The Ratio of minimum to maximum transmission is 0.6482.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeCN'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.028(4)
_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   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.0845
_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^)+(0.1830P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2381
_refine_ls_wR_factor_ref         0.2783
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1858
_reflns_number_total             3164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00666j2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7160582.cif.'
_cod_original_cell_volume        1655.8(9)
_cod_database_code               7160582
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H18A(0.5) H18B(0.5) H18C(0.5) H9A(0.5) H9B(0.5) H9C(0.5) H27A(0.5)
 H27B(0.5) H27C(0.5) H36A(0.5) H36B(0.5) H36C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C12(H12), C14(H14), C13(H13), C4(H4), C3(H3), C2(H2),
 C1(H1), C19(H19), C20(H20), C21(H21), C22(H22), C30(H30), C31(H31), C32(H32),
 C33(H33), C34(H34)
3.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C9(H9A,H9B,H9C), C27(H27A,H27B,H27C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              42004
_olex2_submission_special_instructions 'No special instructions were received'