α-N-phthalimido-oxy isobutyrate-mediated deoxygenative arylation: total synthesis of alanenses A and B
Hyun, Young Eum; Kweon, Jeonguk; Linh Phan, Thi Hieu; Kim, Dongwook; Han, Sunkyu; Chemical Science 16 (2025) 9943–9950; doi:10.1039/D5SC00341E

data_1574522
_publ_section_title
;
 \a-N-phthalimido-oxy isobutyrate-mediated deoxygenative arylation: total
 synthesis of alanenses A and B
;
_journal_issue                   22
_journal_name_full               'Chemical Science'
_journal_page_first              9943
_journal_page_last               9950
_journal_paper_doi               10.1039/D5SC00341E
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C24 H28 O4, 0.5(C6 H14)'
_chemical_formula_sum            'C27 H35 O4'
_chemical_formula_weight         423.55
_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     direct
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-11-18 deposited with the CCDC.	2025-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.4768(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2241(7)
_cell_length_b                   11.8676(6)
_cell_length_c                   14.8052(8)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      2.96
_cell_volume                     2325.7(2)
_computing_cell_refinement       'Bruker APEX4 software'
_computing_data_collection       'Bruker APEX4 software'
_computing_data_reduction        'Bruker APEX4 software'
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'PHOTON II CPAD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1162
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22839
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.051
_diffrn_reflns_theta_min         2.957
_diffrn_source                   'Ius 3.0 microfocus source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       plate
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0390P)^2^+0.6885P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1194
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3043
_reflns_number_total             4578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00341e2.cif
_cod_data_source_block           A23045O_014
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' 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 1574522--1574525.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1574522
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              8377
_shelx_hkl_checksum              49045