Electrochemical strain-release cascade cyclization of N-aryl bicyclobutyl amides with 1,3-dicarbonyl compounds via direct C(sp3)–H/C(sp2)–H functionalization
Zhang, Wen-Yu; Liu, Xin-Yao; Li, Yang; Li, Jin-Heng; Green Chemistry 28 (2026) 2700–2705; doi:10.1039/D5GC06466J

data_7251583
_publ_section_title
;
 Electrochemical strain-release cascade cyclization of N-aryl bicyclobutyl
 amides with 1,3-dicarbonyl compounds via direct C(sp3)--H/C(sp2)--H
 functionalization
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              2700
_journal_page_last               2705
_journal_paper_doi               10.1039/D5GC06466J
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C17 H19 N O5'
_chemical_formula_sum            'C17 H19 N O5'
_chemical_formula_weight         317.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-07-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-11-28 deposited with the CCDC.	2026-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.758(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2763(11)
_cell_length_b                   12.4918(13)
_cell_length_c                   13.2249(13)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    243.00
_cell_measurement_theta_max      68.34
_cell_measurement_theta_min      3.54
_cell_volume                     1597.7(3)
_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      243.00
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13669
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        66.588
_diffrn_reflns_theta_max         66.588
_diffrn_reflns_theta_min         4.748
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6407
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0696 before and 0.0461 after correction.
The Ratio of minimum to maximum transmission is 0.8508.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.917
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0740
_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^)+(0.0954P)^2^+1.2194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1955
_refine_ls_wR_factor_ref         0.1972
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2648
_reflns_number_total             2766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc06466j2.cif
_cod_data_source_block           a
_cod_database_code               7251583
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.855
_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 Ternary CH refined with riding coordinates:
 C6(H6), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C11(H11A,H11B,H11C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              42572
_olex2_submission_special_instructions 'No special instructions were received'