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_4518749
_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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.407(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3338(12)
_cell_length_b                   14.5767(9)
_cell_length_c                   11.8146(14)
_cell_measurement_reflns_used    1612
_cell_measurement_temperature    294.38(10)
_cell_measurement_theta_max      24.3420
_cell_measurement_theta_min      4.1890
_cell_volume                     2233.7(4)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.38(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.816
_diffrn_measured_fraction_theta_max 0.816
_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  24.00   1.00   10.30    --  -17.51 -99.00-120.00   33
  2  \w      2.00  87.00   1.00   10.30    --   19.77  57.00  60.00   85
  3  \w      3.00  28.00   1.00   10.30    --   19.77  77.00 -60.00   25
;
_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      -0.0315800000
_diffrn_orient_matrix_UB_12      -0.0032244000
_diffrn_orient_matrix_UB_13      -0.0570781000
_diffrn_orient_matrix_UB_21      -0.0429718000
_diffrn_orient_matrix_UB_22      0.0153911000
_diffrn_orient_matrix_UB_23      0.0207293000
_diffrn_orient_matrix_UB_31      0.0121953000
_diffrn_orient_matrix_UB_32      0.0460281000
_diffrn_orient_matrix_UB_33      -0.0109338000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.816
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5808
_diffrn_reflns_point_group_measured_fraction_full 0.816
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.310
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90326
_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    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0513P)^2^+0.4958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1362
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2260
_reflns_number_total             3733
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c01466_si_001.cif
_cod_data_source_block           im-21
_cod_original_cell_volume        2233.8(4)
_cod_database_code               4518749
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         C24H21O2Cl
_reflns_odcompleteness_completeness 80.77
_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:
 C27(H27), C9(H9), C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C6(H6), C22(H22), C12(H12), C25(H25), C17(H17), C1(H1), C26(H26),
 C2(H2), C13(H13), C16(H16), C5(H5)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C4(H4A,H4B,H4C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              32534
_shelx_hkl_checksum              90848
_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 1.071
_oxdiff_exptl_absorpt_empirical_full_min 0.925