#------------------------------------------------------------------------------
#$Date: 2021-05-29 00:48:14 +0300 (Sat, 29 May 2021) $
#$Revision: 265593 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/87/4518748.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4518748
loop_
_publ_author_name
'Marpna, Ibakyntiew D.'
'Shangpliang, O. Risuklang'
'Wanniang, Kmendashisha'
'Kshiar, Baskhemlang'
'Lipon, Tyrchain Mitre'
'Laloo, Badaker M.'
'Myrboh, Bekington'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     -9.00  90.00   1.00    1.00    --   20.24  77.00 120.00   99
  2  ω    -25.00  62.00   1.00    1.00    --   20.24 -99.00   0.00   87
  3  ω    -51.00  40.00   1.00    1.00    --   20.24 -37.00-150.00   91
  4  ω     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       'ω 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/[σ²(Fo²)+(0.0511P)²+0.1354P] where P=(Fo²+2Fc²)/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
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
O2 O 0.18463(14) 0.17642(11) 0.33072(10) 0.0377(3) Uani 1.000000 .
O5 O 0.28461(13) 0.41185(11) 0.42577(9) 0.0369(3) Uani 1.000000 .
O3 O -0.00466(14) 0.14910(11) 0.44385(10) 0.0391(3) Uani 1.000000 .
O4 O 0.14041(15) 0.38227(11) 0.56423(10) 0.0464(3) Uani 1.000000 .
O6 O 0.34899(17) 0.66261(12) 0.58025(12) 0.0520(3) Uani 1.000000 .
O1 O -0.07333(15) -0.10717(12) 0.31460(12) 0.0507(3) Uani 1.000000 .
C19 C 0.22989(19) -0.08349(15) 0.33678(13) 0.0328(3) Uani 1.000000 .
C16 C 0.0252(2) 0.27604(15) 0.44793(14) 0.0343(3) Uani 1.000000 .
H16 H -0.0892(2) 0.28474(15) 0.42335(14) 0.0412(4) Uiso 1.000000 R
C18 C 0.0848(2) -0.03314(16) 0.34998(13) 0.0339(3) Uani 1.000000 .
C17 C 0.1409(2) 0.11936(15) 0.41415(14) 0.0337(3) Uani 1.000000 .
H17 H 0.2447(2) 0.16030(15) 0.48951(14) 0.0405(4) Uiso 1.000000 R
C7 C 0.13387(19) 0.28740(15) 0.35606(13) 0.0314(3) Uani 1.000000 .
C8 C 0.3129(2) 0.44203(15) 0.55228(13) 0.0353(4) Uani 1.000000 .
H8 H 0.3976(2) 0.40708(15) 0.58124(13) 0.0424(4) Uiso 1.000000 R
C6 C 0.0406(2) 0.28632(15) 0.23682(14) 0.0339(3) Uani 1.000000 .
C9 C 0.3794(2) 0.59439(16) 0.63045(15) 0.0358(4) Uani 1.000000 .
C20 C 0.4017(2) -0.00135(17) 0.34601(15) 0.0403(4) Uani 1.000000 .
H20 H 0.4294(2) 0.08875(17) 0.36361(15) 0.0484(5) Uiso 1.000000 R
C24 C 0.1929(2) -0.21624(16) 0.31476(15) 0.0418(4) Uani 1.000000 .
H24 H 0.0788(2) -0.27155(16) 0.30956(15) 0.0501(5) Uiso 1.000000 R
C10 C 0.4695(2) 0.65032(17) 0.76548(15) 0.0402(4) Uani 1.000000 .
C21 C 0.5313(2) -0.05366(18) 0.32901(16) 0.0457(4) Uani 1.000000 .
H21 H 0.6453(2) 0.00083(18) 0.33326(16) 0.0548(5) Uiso 1.000000 R
C22 C 0.4921(2) -0.18609(18) 0.30584(15) 0.0448(4) Uani 1.000000 .
H22 H 0.5793(2) -0.22108(18) 0.29376(15) 0.0537(5) Uiso 1.000000 R
C5 C 0.0088(2) 0.39808(17) 0.24142(16) 0.0447(4) Uani 1.000000 .
H5 H 0.0460(2) 0.47317(17) 0.31724(16) 0.0536(5) Uiso 1.000000 R
C23 C 0.3240(2) -0.26695(18) 0.30048(17) 0.0483(4) Uani 1.000000 .
H23 H 0.2990(2) -0.35566(18) 0.28726(17) 0.0580(5) Uiso 1.000000 R
C1 C -0.0163(3) 0.17503(19) 0.12413(16) 0.0535(5) Uani 1.000000 .
H1 H 0.0035(3) 0.09910(19) 0.12044(16) 0.0642(6) Uiso 1.000000 R
C11 C 0.5017(3) 0.78287(19) 0.83979(18) 0.0595(5) Uani 1.000000 .
H11 H 0.4655(3) 0.83364(19) 0.80413(18) 0.0714(6) Uiso 1.000000 R
C4 C -0.0785(3) 0.3981(2) 0.1331(2) 0.0597(5) Uani 1.000000 .
H4 H -0.1005(3) 0.4731(2) 0.1363(2) 0.0717(6) Uiso 1.000000 R
C15 C 0.5238(3) 0.5767(2) 0.82026(18) 0.0610(5) Uani 1.000000 .
H15 H 0.5013(3) 0.4872(2) 0.77191(18) 0.0731(6) Uiso 1.000000 R
C3 C -0.1328(3) 0.2877(3) 0.02110(19) 0.0675(6) Uani 1.000000 .
H3 H -0.1898(3) 0.2885(3) -0.05179(19) 0.0810(7) Uiso 1.000000 R
C2 C -0.1031(3) 0.1768(2) 0.01668(18) 0.0699(6) Uani 1.000000 .
H2 H -0.1416(3) 0.1016(2) -0.05929(18) 0.0838(7) Uiso 1.000000 R
C13 C 0.6428(3) 0.7657(3) 1.0188(2) 0.0847(8) Uani 1.000000 .
H13 H 0.7019(3) 0.8048(3) 1.1040(2) 0.1016(10) Uiso 1.000000 R
C12 C 0.5868(3) 0.8396(3) 0.9657(2) 0.0825(8) Uani 1.000000 .
H12 H 0.6067(3) 0.9282(3) 1.0152(2) 0.0990(9) Uiso 1.000000 R
C14 C 0.6119(3) 0.6357(3) 0.9471(2) 0.0832(7) Uani 1.000000 .
H14 H 0.6501(3) 0.5861(3) 0.9834(2) 0.0999(9) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 C17 108.39(10) . . ?
C8 O5 C7 107.85(11) . . ?
C17 O3 C16 106.38(10) . . ?
C8 O4 C16 108.87(11) . . ?
C20 C19 C18 121.89(14) . . ?
C24 C19 C18 118.91(13) . . ?
C24 C19 C20 119.20(14) . . ?
O4 C16 O3 112.89(13) . . ?
H16 C16 O3 111.34(7) . . ?
H16 C16 O4 111.34(8) . . ?
C7 C16 O3 104.91(11) . . ?
C7 C16 O4 104.65(11) . . ?
C7 C16 H16 111.34(8) . . ?
C19 C18 O1 122.83(15) . . ?
C17 C18 O1 119.38(14) . . ?
C17 C18 C19 117.77(12) . . ?
O3 C17 O2 105.49(11) . . ?
C18 C17 O2 109.92(12) . . ?
C18 C17 O3 110.43(12) . . ?
H17 C17 O2 110.30(7) . . ?
H17 C17 O3 110.30(8) . . ?
H17 C17 C18 110.30(8) . . ?
O5 C7 O2 111.91(11) . . ?
C16 C7 O2 103.29(11) . . ?
C16 C7 O5 104.12(11) . . ?
C6 C7 O2 110.84(12) . . ?
C6 C7 O5 108.69(12) . . ?
C6 C7 C16 117.81(12) . . ?
O4 C8 O5 106.46(12) . . ?
H8 C8 O5 111.13(8) . . ?
H8 C8 O4 111.13(8) . . ?
C9 C8 O5 110.44(12) . . ?
C9 C8 O4 106.35(12) . . ?
C9 C8 H8 111.13(8) . . ?
C5 C6 C7 119.16(14) . . ?
C1 C6 C7 121.18(15) . . ?
C1 C6 C5 119.65(16) . . ?
C8 C9 O6 118.92(14) . . ?
C10 C9 O6 122.81(15) . . ?
C10 C9 C8 118.18(14) . . ?
H20 C20 C19 120.01(9) . . ?
C21 C20 C19 119.98(15) . . ?
C21 C20 H20 120.01(10) . . ?
H24 C24 C19 119.76(9) . . ?
C23 C24 C19 120.48(15) . . ?
C23 C24 H24 119.76(10) . . ?
C11 C10 C9 118.35(16) . . ?
C15 C10 C9 122.76(16) . . ?
C15 C10 C11 118.89(17) . . ?
H21 C21 C20 119.91(10) . . ?
C22 C21 C20 120.19(15) . . ?
C22 C21 H21 119.91(9) . . ?
H22 C22 C21 119.92(9) . . ?
C23 C22 C21 120.17(16) . . ?
C23 C22 H22 119.92(10) . . ?
H5 C5 C6 120.06(10) . . ?
C4 C5 C6 119.88(17) . . ?
C4 C5 H5 120.06(12) . . ?
C22 C23 C24 119.94(16) . . ?
H23 C23 C24 120.03(10) . . ?
H23 C23 C22 120.03(10) . . ?
H1 C1 C6 120.13(10) . . ?
C2 C1 C6 119.74(19) . . ?
C2 C1 H1 120.13(13) . . ?
H11 C11 C10 119.81(12) . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.81(16) . . ?
H4 C4 C5 119.90(12) . . ?
C3 C4 C5 120.19(19) . . ?
C3 C4 H4 119.90(12) . . ?
H15 C15 C10 119.92(11) . . ?
C14 C15 C10 120.2(2) . . ?
C14 C15 H15 119.92(16) . . ?
H3 C3 C4 120.03(12) . . ?
C2 C3 C4 119.95(18) . . ?
C2 C3 H3 120.03(12) . . ?
C3 C2 C1 120.6(2) . . ?
H2 C2 C1 119.71(13) . . ?
H2 C2 C3 119.71(12) . . ?
C12 C13 H13 119.95(14) . . ?
C14 C13 H13 119.95(15) . . ?
C14 C13 C12 120.1(2) . . ?
C13 C12 C11 120.2(2) . . ?
H12 C12 C11 119.92(16) . . ?
H12 C12 C13 119.92(14) . . ?
C13 C14 C15 120.3(2) . . ?
H14 C14 C15 119.84(16) . . ?
H14 C14 C13 119.84(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C17 1.4233(17) . ?
O2 C7 1.4181(18) . ?
O5 C7 1.4128(17) . ?
O5 C8 1.4015(17) . ?
O3 C16 1.3947(18) . ?
O3 C17 1.4037(17) . ?
O4 C16 1.4101(18) . ?
O4 C8 1.4211(18) . ?
O6 C9 1.2108(19) . ?
O1 C18 1.2070(18) . ?
C19 C18 1.482(2) . ?
C19 C20 1.390(2) . ?
C19 C24 1.386(2) . ?
C16 H16 0.9800 . ?
C16 C7 1.548(2) . ?
C18 C17 1.529(2) . ?
C17 H17 0.9800 . ?
C7 C6 1.508(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.533(2) . ?
C6 C5 1.382(2) . ?
C6 C1 1.379(2) . ?
C9 C10 1.476(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(2) . ?
C24 H24 0.9300 . ?
C24 C23 1.380(2) . ?
C10 C11 1.387(2) . ?
C10 C15 1.379(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.376(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.377(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.382(2) . ?
C23 H23 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.382(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.372(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.385(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.364(3) . ?
C2 H2 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.374(4) . ?
C13 C14 1.359(4) . ?
C12 H12 0.9300 . ?
C14 H14 0.9300 . ?
