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_7062091
_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_absolute_configuration ad
_chemical_formula_moiety         'C21 H18 N0 O3'
_chemical_formula_sum            'C21 H18 N0 O3'
_chemical_formula_weight         318.35
_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
_audit_creation_date             2022-07-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-07-06 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.501(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.44830(10)
_cell_length_b                   9.97000(10)
_cell_length_c                   9.7662(2)
_cell_measurement_reflns_used    28096
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      60.4560
_cell_measurement_theta_min      4.4640
_cell_volume                     808.48(3)
_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 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0995
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33268
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.433
_diffrn_reflns_theta_min         4.479
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65670
_exptl_absorpt_correction_type   multi-scan
_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    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1587 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3678
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0470P)^2^+0.0804P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0813
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3538
_reflns_number_total             3678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj03473e2.cif
_cod_data_source_block           20220602CL-2_autored
_cod_depositor_comments
'Adding full bibliography for 7062089--7062092.cif.'
_cod_original_cell_volume        808.48(2)
_cod_database_code               7062091
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C5(H5), C1(H1)
1.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
1.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C24(H24), C23(H23), C20(H20), C21(H21), C22(H22),
 C13(H13), C14(H14), C12(H12)
;
_shelx_res_checksum              59582
_olex2_submission_special_instructions 'No special instructions were received'