Brønsted acid- and Ni(II)-catalyzed C-H oxidation/rearrangement of cyclotriveratrylenes (CTVs) to cyclic and acyclic quinones as potential anti-cancer agents.
Darole, Ratanamala S.; Choudhary, Shailendra Singh; Sharma, Himanshu; Mali, Bhupendra P.; Gopu, Booblan; Vanka, Kumar; Senthilkumar, Beeran; Organic & biomolecular chemistry 22 (2024) 1038–1046; doi:10.1039/d3ob01428b

data_7159755
_publ_section_title
;
 Br&#xf8;nsted acid- and Ni(II)-catalyzed C-H oxidation/rearrangement of
 cyclotriveratrylenes (CTVs) to cyclic and acyclic quinones as potential
 anti-cancer agents.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1038
_journal_page_last               1046
_journal_paper_doi               10.1039/d3ob01428b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C5 H5 O2'
_chemical_formula_sum            'C5 H5 O2'
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_space_group_name_Hall           'C -2y'
_space_group_name_H-M_alt        'C 1 m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-12-12 deposited with the CCDC.	2023-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.453(3)
_cell_angle_gamma                90
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_cell_length_c                   4.3338(4)
_cell_measurement_reflns_used    6752
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.57
_cell_measurement_theta_min      2.55
_cell_volume                     435.14(7)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
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_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_min         2.552
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.115
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_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 656 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
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_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0493P)^2^+0.0820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0858
_reflns_Friedel_coverage         0.982
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                1406
_reflns_number_total             1518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01428b2.cif
_cod_data_source_block           3c
_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 7159755--7159758.cif.
;
_cod_original_sg_symbol_H-M      'C m'
_cod_database_code               7159755
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              70729