Rapid construction of furan-linked bisheterocycles <i>via</i> a palladium-catalyzed domino Heck/cross-coupling reaction.
Wang, Du; Yin, Zhilong; Feng, Xueli; Zhu, Huixuan; Gao, Fan; Li, Jiaxin; Zhang, Jingli; Yuan, Ye; Organic & biomolecular chemistry 23 (2025) 8267–8273; doi:10.1039/d5ob01081k

data_7160690
_publ_section_title
;
 Rapid construction of furan-linked bisheterocycles <i>via</i> a
 palladium-catalyzed domino Heck/cross-coupling reaction.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8267
_journal_page_last               8273
_journal_paper_doi               10.1039/d5ob01081k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C25 H26 Cl N O2'
_chemical_formula_sum            'C25 H26 Cl N O2'
_chemical_formula_weight         407.92
_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     dual
_audit_creation_date             2025-08-16
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-08-16 deposited with the CCDC.	2025-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                112.366(3)
_cell_angle_beta                 113.513(3)
_cell_angle_gamma                97.671(3)
_cell_formula_units_Z            2
_cell_length_a                   10.7758(11)
_cell_length_b                   11.2002(11)
_cell_length_c                   11.2071(11)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      71.96
_cell_measurement_theta_min      3.94
_cell_volume                     1080.12(19)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XM  (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'Image Plate'
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.802
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Photon III'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.802
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20144
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.802
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         72.351
_diffrn_reflns_theta_min         3.943
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           3.57
_diffrn_source_power             0.250
_diffrn_source_target            Mo
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.130
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.045(5)
_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   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         5202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0661P)^2^+0.2880P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4613
_reflns_number_total             5202
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01081k2.cif
_cod_data_source_block           211014h_0m
_cod_depositor_comments
'Adding full bibliography for 7160690--7160691.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7160690
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.895
_shelx_estimated_absorpt_t_min   0.876
_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
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C13(H13), C17(H17), C18(H18), C19(H19), C20(H20),
 C25(H25)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              98923
_olex2_submission_special_instructions 'No special instructions were received'