Catalytic synthesis of seven-membered carbocycles via ring expansion of cyclic β-ketoesters
Chen, Li; Huang, Huangjiang; Luo, Benlong; Liu, Jinggong; Yang, Shuang; Fang, Xinqiang; New Journal of Chemistry 47 (2023) 41–45; doi:10.1039/D2NJ03473E

data_7062090
_publ_section_title
;
 Catalytic synthesis of seven-membered carbocycles via ring expansion of
 cyclic \b-ketoesters
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              41
_journal_page_last               45
_journal_paper_doi               10.1039/D2NJ03473E
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C23 H20 O5'
_chemical_formula_sum            'C23 H20 O5'
_chemical_formula_weight         376.39
_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
_audit_creation_date             2022-03-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-07-07 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_cell_angle_alpha                84.259(7)
_cell_angle_beta                 69.811(8)
_cell_angle_gamma                69.254(7)
_cell_formula_units_Z            2
_cell_length_a                   8.6573(7)
_cell_length_b                   10.0811(7)
_cell_length_c                   12.3197(11)
_cell_measurement_reflns_used    10335
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      60.4360
_cell_measurement_theta_min      4.0700
_cell_volume                     943.41(15)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12253
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.334
_diffrn_reflns_theta_min         4.078
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.486
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82314
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_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0099(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0369P)^2^+0.3717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3960
_reflns_number_total             4188
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj03473e2.cif
_cod_data_source_block           cl-1_auto
_cod_depositor_comments
'Adding full bibliography for 7062089--7062092.cif.'
_cod_original_cell_volume        943.40(15)
_cod_database_code               7062090
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B)
1.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C21(H21), C20(H20), C19(H19), C13(H13),
 C22(H22), C12(H12), C14(H14)
1.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
1.d Idealised tetrahedral OH refined as rotating group:
 O28(H28)
;
_shelx_res_checksum              55807
_olex2_submission_special_instructions 'No special instructions were received'