NaIO<sub>4</sub>-driven oxidative dimerization and Cu(I)-catalyzed oxidative decarbonylation: modular synthesis of 1,2-naphthoquinones and aryl naphtho[2,<i>b</i>]furans.
Ahmad, Mudassir; Rather, Gowhar Ahmad; Rashid Tarray, Amir; Lone, Waseem I.; Rashid, Showkat; Organic & biomolecular chemistry 23 (2025) 7724–7730; doi:10.1039/d5ob01064k

data_7160654
_publ_section_title
;
 NaIO<sub>4</sub>-driven oxidative dimerization and Cu(I)-catalyzed
 oxidative decarbonylation: modular synthesis of 1,2-naphthoquinones and
 aryl naphtho[2,<i>b</i>]furans.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7724
_journal_page_last               7730
_journal_paper_doi               10.1039/d5ob01064k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C19 H12 O3'
_chemical_formula_sum            'C19 H12 O3'
_chemical_formula_weight         288.29
_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
_audit_creation_date             2025-05-30
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2025.05.22 svn.r631f81ec for OlexSys, GUI svn.r7248)
;
_audit_update_record
;
2025-06-20 deposited with the CCDC.	2025-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.6180(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.8830(6)
_cell_length_b                   7.0571(2)
_cell_length_c                   24.4179(8)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.42
_cell_volume                     2899.83(16)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0555
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            43732
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.288
_diffrn_reflns_theta_min         2.698
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1094 before and 0.0585 after correction.
The Ratio of minimum to maximum transmission is 0.9041.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         7200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0411P)^2^+1.5904P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1228
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5350
_reflns_number_total             7200
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01064k2.cif
_cod_data_source_block           5mayb_0m_a
_cod_depositor_comments          'Adding full bibliography for 7160654.cif.'
_cod_database_code               7160654
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.988
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C36(H36), C22(H22), C28(H28), C20(H20), C8(H8), C25(H25), C16(H16), C30(H30),
 C7(H7), C23(H23), C5(H5), C35(H35), C14(H14), C31(H31), C12(H12), C24(H24),
 C6(H6A), C15(H15), C3(H3A), C2(H2), C33(H33), C34(H34)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;
_shelx_res_checksum              23761
_olex2_submission_special_instructions 'No special instructions were received'