Organic redox cascade cyclization of 2-alkynylquinones by ascorbic acid in combination with a copper catalyst and its application to formal synthesis of liphagal
Jeong, Taejoo; Okanishi, Yusuke; Yotsui, Sora; Kim, In Su; Yoshimitsu, Takehiko; New Journal of Chemistry 47 (2023) 3425–3429; doi:10.1039/D2NJ05724G

data_7062240
_publ_section_title
;
 Organic redox cascade cyclization of 2-alkynylquinones by ascorbic acid
 in combination with a copper catalyst and its application to formal
 synthesis of liphagal
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3425
_journal_page_last               3429
_journal_paper_doi               10.1039/D2NJ05724G
_journal_volume                  47
_journal_year                    2023
_chemical_formula_sum            'C15 H12 O3'
_chemical_formula_weight         240.25
_chemical_name_common            TJ-PhBF
_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_update_record
;
2022-02-15 deposited with the CCDC.	2023-01-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.089(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3998(14)
_cell_length_b                   5.6694(9)
_cell_length_c                   12.814(2)
_cell_measurement_reflns_used    7901
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      25.1218
_cell_measurement_theta_min      2.5236
_cell_volume                     586.32(16)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service v2021.1.0.1'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24439
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         1.65
_diffrn_source_current           30.0
_diffrn_source_power             1.50
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.132
_refine_ls_abs_structure_details
;

Flack x determined using 840 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   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2895
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0452P)^2^+0.0335P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0957
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2369
_reflns_number_total             2895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05724g2.cif
_cod_data_source_block           yy081
_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 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7062240.cif.
;
_cod_original_cell_volume        586.32(17)
_cod_database_code               7062240
_shelx_res_checksum              63493