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_4518753
_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         'C30 H30 O6'
_chemical_formula_sum            'C30 H30 O6'
_chemical_formula_weight         486.54
_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             2019-01-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                103.762(7)
_cell_angle_beta                 96.584(6)
_cell_angle_gamma                90.048(6)
_cell_formula_units_Z            2
_cell_length_a                   9.1302(6)
_cell_length_b                   11.5971(10)
_cell_length_c                   12.5478(9)
_cell_measurement_reflns_used    2160
_cell_measurement_temperature    293.55(11)
_cell_measurement_theta_max      28.5810
_cell_measurement_theta_min      3.8730
_cell_volume                     1281.41(17)
_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      293.55(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_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  89.00   1.00    5.75    --   19.93  37.00  30.00   95
  2  \w     38.00  94.00   1.00    5.75    --   19.93 178.00-120.00   56
  3  \w    -36.00  60.00   1.00    5.75    --   19.93 -19.00-180.00   96
  4  \w    -24.00  20.00   1.00    5.75    --  -17.51 -99.00-150.00   44
  5  \w    -24.00  24.00   1.00    5.75    --  -17.51 -99.00  30.00   48
;
_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      0.0162615000
_diffrn_orient_matrix_UB_12      -0.0611880000
_diffrn_orient_matrix_UB_13      -0.0105341000
_diffrn_orient_matrix_UB_21      -0.0138140000
_diffrn_orient_matrix_UB_22      -0.0044353000
_diffrn_orient_matrix_UB_23      -0.0576446000
_diffrn_orient_matrix_UB_31      0.0752704000
_diffrn_orient_matrix_UB_32      0.0143124000
_diffrn_orient_matrix_UB_33      -0.0010998000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8081
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         3.367
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85435
_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    1.261
_exptl_crystal_description       needle
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0573P)^2^+0.0288P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1271
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3520
_reflns_number_total             5199
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c01466_si_001.cif
_cod_data_source_block           im-23
_cod_original_cell_volume        1281.42(18)
_cod_database_code               4518753
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         C30H18O6
_reflns_odcompleteness_completeness 99.10
_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), C21(H21), C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C7(H7), C30(H30), C19(H19), C15(H15), C6(H6), C29(H29), C18(H18),
 C3(H3)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C14(H14A,H14B,H14C), C28(H28A,H28B,H28C), C2(H2A,H2B,
 H2C), C5(H5A,H5B,H5C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              65407
_shelx_hkl_checksum              49792
_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 1.196
_oxdiff_exptl_absorpt_empirical_full_min 0.668