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_4518751
_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         'C27 H24 O6'
_chemical_formula_sum            'C27 H24 O6'
_chemical_formula_weight         444.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                84.965(3)
_cell_angle_beta                 71.990(5)
_cell_angle_gamma                81.260(4)
_cell_formula_units_Z            2
_cell_length_a                   9.8005(6)
_cell_length_b                   10.7669(4)
_cell_length_c                   11.3858(6)
_cell_measurement_reflns_used    2104
_cell_measurement_temperature    292.0(6)
_cell_measurement_theta_max      28.3020
_cell_measurement_theta_min      3.9140
_cell_volume                     1128.24(11)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.0(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.907
_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     -6.00  73.00   1.00   12.49    --   19.77  37.00 -90.00   79
  2  \w     -8.00  93.00   1.00   12.49    --   19.77  19.00-180.00  101
  3  \w    -23.00  23.00   1.00   12.49    --  -17.51 -99.00 -30.00   46
  4  \w    -82.00 -56.00   1.00   12.49    --  -17.51 146.00  41.00   26
;
_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      0.0011769000
_diffrn_orient_matrix_UB_12      0.0080312000
_diffrn_orient_matrix_UB_13      -0.0627925000
_diffrn_orient_matrix_UB_21      0.0759850000
_diffrn_orient_matrix_UB_22      0.0004960000
_diffrn_orient_matrix_UB_23      -0.0182333000
_diffrn_orient_matrix_UB_31      0.0109006000
_diffrn_orient_matrix_UB_32      -0.0662278000
_diffrn_orient_matrix_UB_33      -0.0048856000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.914
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5305
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.318
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95060
_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    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0465P)^2^+0.2187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3101
_reflns_number_total             4195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c01466_si_001.cif
_cod_data_source_block           im-36
_cod_database_code               4518751
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         C27H24O6
_reflns_odcompleteness_completeness 90.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C3(H3), C24(H24), C26(H26), C14(H14), C6(H6), C25(H25), C4(H4),
 C5(H5), C15(H15), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C1(H1A,H1B,H1C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              4495
_shelx_hkl_checksum              88728
_shelx_fab_checksum              57656
_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 1.067
_oxdiff_exptl_absorpt_empirical_full_min 0.944