Palladium-catalyzed decarboxylative (4 + 3) cycloadditions of bicyclobutanes with 2-alkylidenetrimethylene carbonates for the synthesis of 2-oxabicyclo[4.1.1]octanes.
Gao, Xin-Yu; Tang, Lei; Zhang, Xu; Feng, Jian-Jun; Chemical science 15 (2024) 13942–13948; doi:10.1039/d4sc02998d

data_1572301
_publ_section_title
;
 Palladium-catalyzed decarboxylative (4 + 3) cycloadditions of
 bicyclobutanes with 2-alkylidenetrimethylene carbonates for the synthesis
 of 2-oxabicyclo[4.1.1]octanes.
;
_journal_issue                   34
_journal_name_full               'Chemical science'
_journal_page_first              13942
_journal_page_last               13948
_journal_paper_doi               10.1039/d4sc02998d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C25 H22 O2'
_chemical_formula_sum            'C25 H22 O2'
_chemical_formula_weight         354.42
_chemical_name_systematic
(Z)-(4-benzylidene-2-oxabicyclo[4.1.1]octan-6-yl)(naphthalen-2-yl)methanone
_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             2024-01-12
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Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_audit_update_record
;
2024-04-30 deposited with the CCDC.	2024-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                113.1360(10)
_cell_angle_beta                 99.6000(10)
_cell_angle_gamma                90.4920(10)
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_cell_length_b                   11.9065(3)
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_cell_measurement_temperature    150.00
_cell_measurement_theta_max      68.118
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_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
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_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APX-II'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
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_diffrn_reflns_limit_k_min       -14
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_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12220
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.263
_diffrn_reflns_theta_min         3.400
_diffrn_source_current           1.2
_diffrn_source_power             0.06
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_exptl_absorpt_correction_T_max  0.975
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_exptl_absorpt_correction_type   multi-scan
_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    1.255
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0030(6)
_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   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0444P)^2^+0.2247P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0958
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3062
_reflns_number_total             3424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02998d2.cif
_cod_data_source_block           cu_2024011201_0m
_cod_depositor_comments          'Adding full bibliography for 1572301.cif.'
_cod_database_code               1572301
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.818
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C13(H13A,H13B), C16(H16A,H16B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C19(H19), C21(H21), C25(H25), C3(H3), C8(H8), C4(H4), C22(H22),
 C24(H24), C5(H5), C23(H23), C7(H7), C6(H6)
;
_shelx_res_checksum              54007
_shelx_hkl_checksum              14160
_olex2_submission_special_instructions 'No special instructions were received'