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_4518752
_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 O9'
_chemical_formula_sum            'C27 H24 O9'
_chemical_formula_weight         492.49
_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'
_symmetry_Int_Tables_number      14
_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                90
_cell_angle_beta                 100.869(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0530(6)
_cell_length_b                   24.436(3)
_cell_length_c                   12.3129(12)
_cell_measurement_reflns_used    1536
_cell_measurement_temperature    294.1(7)
_cell_measurement_theta_max      26.1470
_cell_measurement_theta_min      3.7310
_cell_volume                     2379.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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      294.1(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1279
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9927
_diffrn_measured_fraction_theta_max 0.9920
_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    -23.00  24.00   1.00   12.13    --  -17.51 -99.00 -60.00   47
  2  \w     59.00  96.00   1.00   12.13    --   19.69-178.00-150.00   37
  3  \w    -30.00  84.00   1.00   12.13    --   19.69   0.00 120.00  114
;
_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      0.0387940000
_diffrn_orient_matrix_UB_12      -0.0009367000
_diffrn_orient_matrix_UB_13      0.0566751000
_diffrn_orient_matrix_UB_21      0.0014902000
_diffrn_orient_matrix_UB_22      -0.0290113000
_diffrn_orient_matrix_UB_23      -0.0024252000
_diffrn_orient_matrix_UB_31      0.0808017000
_diffrn_orient_matrix_UB_32      0.0010101000
_diffrn_orient_matrix_UB_33      -0.0148993000
_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  0.0273
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9256
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.26
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.3746
_exptl_crystal_description       needle
_exptl_crystal_F_000             1032.6789
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.2773
_refine_diff_density_min         -0.3618
_refine_diff_density_rms         0.0694
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             6.2521
_refine_ls_goodness_of_fit_ref   1.0617
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0617
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0453P)^2^+0.3552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1366
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -10
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              -6
_reflns_number_gt                2854
_reflns_number_total             4822
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ao1c01466_si_001.cif
_cod_data_source_block           IM-59
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               4518752
_chemical_oxdiff_formula         C27H24O9
_reflns_odcompleteness_completeness 98.94
_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:
 C18(H18), C3aa(H3aa), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C15(H15), C4(H4), C21(H21), C3(H3), C12(H12), C14(H14),
 C24(H24), C13(H13), C23(H23), C22(H22)
2.c Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c), C26(H26a,H26b,H26c), C17(H17a,H17b,H17c)
;
_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 1.212
_oxdiff_exptl_absorpt_empirical_full_min 0.542