Synthesis of bicyclo[3.2.0]heptane lactones via a ligand-enabled Pd-catalyzed C(sp3)–H activation cascade
Fan, Zhoulong; Cai, Xinpei; Sheng, Tao; Yu, Jin-Quan; Chemical Science 16 (2025) 9436–9440; doi:10.1039/D5SC00711A

data_1574549
_publ_section_title
;
 Synthesis of bicyclo[3.2.0]heptane lactones via a ligand-enabled
 Pd-catalyzed C(sp3)--H activation cascade
;
_journal_issue                   21
_journal_name_full               'Chemical Science'
_journal_page_first              9436
_journal_page_last               9440
_journal_paper_doi               10.1039/D5SC00711A
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C13 H14 O3'
_chemical_formula_sum            'C13 H14 O3'
_chemical_formula_weight         218.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-29
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_audit_update_record
;
2022-08-29 deposited with the CCDC.	2025-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.142(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5249(6)
_cell_length_b                   7.7533(9)
_cell_length_c                   11.3333(10)
_cell_measurement_reflns_used    7129
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      3.21
_cell_volume                     558.33(10)
_computing_cell_refinement       'SAINT v8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 v2022.1-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT v8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker Photon III Area Detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17343
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.743
_diffrn_reflns_theta_min         3.211
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1530 before and 0.0685 after correction.
The Ratio of minimum to maximum transmission is 0.9159.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       plank
_exptl_crystal_F_000             232
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Hexane'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 814 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2381
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0667P)^2^+0.1609P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1387
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2063
_reflns_number_total             2381
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00711a2.cif
_cod_data_source_block           yu167
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1574549--1574550.cif.
;
_cod_database_code               1574549
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.978
_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. Restrained distances
 C5-C3 \\sim C5-C3'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C3) = Uanis(C3')
4. Rigid body (RIGU) restrains
 O1', C1', C2', C3', C4', O2'
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Same fragment restrains
{O1, O2, C1, C2, C3, C4} sigma for 1-2: 0.02, 1-3: 0.04
as in
{O1', O2', C1', C2', C3', C4'}
6. Others
 Sof(O1')=Sof(O2')=Sof(C1')=Sof(C2')=Sof(H2'A)=Sof(H2'B)=Sof(C3')=Sof(H3')=
 Sof(C4')=Sof(H4'A)=Sof(H4'B)=Sof(H5B)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(C1)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3)=Sof(C4)=
 Sof(H4A)=Sof(H4B)=Sof(H5A)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C3(H3), C3'(H3')
7.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C2'(H2'A,H2'B), C4'(H4'A,H4'B)
7.c Aromatic/amide H refined with riding coordinates:
 C5(H5A), C5(H5B), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
7.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              27365
_olex2_submission_special_instructions 'No special instructions were received'