Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of Acetophenones in the Presence of SeO2: A Serendipitous Approach for the Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles
Marpna, Ibakyntiew D.; Shangpliang, O. Risuklang; Wanniang, Kmendashisha; Kshiar, Baskhemlang; Lipon, Tyrchain Mitre; Laloo, Badaker M.; Myrboh, Bekington; ACS Omega  (2021) –; doi:10.1021/acsomega.1c01466

data_4518748
_publ_section_title
;
 Trifluoroacetic Acid-Mediated Oxidative Self-Condensation of
 Acetophenones in the Presence of SeO2: A Serendipitous Approach for the
 Synthesis of Fused [1,3]Dioxolo[4,5-d][1,3]dioxoles
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.1c01466
_journal_year                    2021
_chemical_formula_moiety         'C24 H18 O6'
_chemical_formula_sum            'C24 H18 O6'
_chemical_formula_weight         402.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                110.821(8)
_cell_angle_beta                 99.527(7)
_cell_angle_gamma                108.076(8)
_cell_formula_units_Z            2
_cell_length_a                   8.1723(8)
_cell_length_b                   11.5815(10)
_cell_length_c                   12.0792(10)
_cell_measurement_reflns_used    2030
_cell_measurement_temperature    293.80(18)
_cell_measurement_theta_max      28.7400
_cell_measurement_theta_min      5.0640
_cell_volume                     965.69(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.80(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9947
_diffrn_measured_fraction_theta_max 0.9929
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     -9.00  90.00   1.00    1.00    --   20.24  77.00 120.00   99
  2  \w    -25.00  62.00   1.00    1.00    --   20.24 -99.00   0.00   87
  3  \w    -51.00  40.00   1.00    1.00    --   20.24 -37.00-150.00   91
  4  \w     23.00  88.00   1.00    1.00    --   20.24  57.00-150.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0333891000
_diffrn_orient_matrix_UB_12      0.0304890000
_diffrn_orient_matrix_UB_13      0.0660211000
_diffrn_orient_matrix_UB_21      -0.0515024000
_diffrn_orient_matrix_UB_22      -0.0616579000
_diffrn_orient_matrix_UB_23      0.0003235000
_diffrn_orient_matrix_UB_31      0.0738713000
_diffrn_orient_matrix_UB_32      -0.0195417000
_diffrn_orient_matrix_UB_33      -0.0029454000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6706
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.44
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.3838
_exptl_crystal_description       block
_exptl_crystal_F_000             420.2581
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.2263
_refine_diff_density_min         -0.3129
_refine_diff_density_rms         0.0599
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             5.9147
_refine_ls_goodness_of_fit_ref   1.0686
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0686
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+0.1354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1134
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -14
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3101
_reflns_number_total             3918
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ao1c01466_si_001.cif
_cod_data_source_block           IM-24
_cod_original_cell_volume        965.68(18)
_cod_database_code               4518748
_chemical_oxdiff_formula         C24H18O6
_reflns_odcompleteness_completeness 99.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C17(H17), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C24(H24), C21(H21), C22(H22), C5(H5), C23(H23), C1(H1), C11(H11),
 C4(H4), C15(H15), C3(H3), C2(H2), C13(H13), C12(H12), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.839