#------------------------------------------------------------------------------
#$Date: 2026-05-14 00:24:51 +0200 (Thu 14 de May de 2026) $
#$Revision: 305959 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/1/57/72/1577259.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_1577259
loop_
_publ_author_name
'Lennox, Cameron B.'
'Taylor, Christopher'
'Huskić, Igor'
'Vainauskas, Jogirdas'
'Nickels, Christopher'
'Stein, Robin S.'
'Borchers, Tristan H.'
'Lutton Gething, A.R. Bonnie J.'
'Marrett, Joseph M.'
'Day, Graeme Matthew'
'Friščić, Tomislav'
_publ_section_title
;
 The elusive endo-product of the archetypal Diels-Alder reaction of furan
 and maleic anhydride -- observed in the solid state at last
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC06724C
_journal_year                    2026
_chemical_formula_moiety         '2(C8 H6 O4)'
_chemical_formula_sum            'C16 H12 O8'
_chemical_formula_weight         332.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-05-30
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-11 deposited with the CCDC.	2026-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.247(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8895(13)
_cell_length_b                   5.3562(4)
_cell_length_c                   11.8978(13)
_cell_measurement_reflns_used    5444
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.4000
_cell_measurement_theta_min      4.4820
_cell_volume                     710.86(13)
_computing_cell_refinement       'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.116a 64-bit (release 22-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -12.00   1.00    1.00    --  -39.71 -57.00 -86.00   39
  2  ω   -111.00 -60.00   1.00    1.00    --  -39.71 -57.00 -86.00   51
  3  ω     38.00  63.00   1.00    1.00    --   39.71  57.00  55.00   25
  4  ω     84.00 109.00   1.00    1.00    --  113.00  57.00  55.00   25
  5  ω    142.00 169.00   1.00    1.00    --  113.00  57.00  55.00   27
  6  ω    107.00 134.00   1.00    1.00    --  113.00 -57.00 -86.00   27
  7  ω    -43.00 -13.00   1.00    1.00    --  -39.71 -38.00 -90.00   30
  8  ω    -54.00  34.00   1.00    1.00    --  -39.71  57.00  55.00   88
  9  ω    -69.00   6.00   1.00    1.00    --  -39.71  57.00-150.00   75
 10  ω      3.00  31.00   1.00    1.00    --   39.71  87.00 108.26   28
 11  ω     31.00  86.00   1.00    1.00    --   39.71-125.00 120.00   55
 12  ω      7.00  79.00   1.00    1.00    --   39.71 -99.00-120.00   72
 13  ω    -26.00  54.00   1.00    1.00    --   39.71 -57.00 -86.00   80
 14  ω      3.00  28.00   1.00    1.00    --   40.00  89.00 -72.53   25
 15  ω     14.00  39.00   1.00    1.00    --   48.00  79.00-126.74   25
 16  ω     14.00  41.00   1.00    1.00    --   48.00  78.00  79.38   27
 17  ω     13.00  38.00   1.00    1.00    --   48.00  81.00   6.08   25
 18  ω     15.00  40.00   1.00    1.00    --   48.00  79.00 178.45   25
 19  ω     29.00  77.00   1.00    1.00    --   56.00  68.00 -40.16   48
 20  ω     24.00 110.00   1.00    1.00    --   56.00  68.00  50.52   86
 21  ω     32.00  88.00   1.00    1.00    --   60.00  68.00 142.14   56
 22  ω     91.00 124.00   1.00    1.00    --   60.00  68.00 142.14   33
 23  ω     31.00  70.00   1.00    1.00    --   60.00  68.00 -71.22   39
 24  ω     34.00  67.00   1.00    1.00    --   64.00  61.00-160.37   33
 25  ω     37.00  79.00   1.00    1.00    --   68.00  70.00 102.61   42
 26  ω     38.00  89.00   1.00    1.00    --   68.00  70.00-151.19   51
 27  ω     37.00 140.00   1.00    1.00    --   68.00  71.00 -16.62  103
 28  ω    121.00 148.00   1.00    1.00    --   72.00  69.00-120.49   27
 29  ω     43.00  72.00   1.00    1.00    --   72.00  69.00-120.49   29
 30  ω     46.00 107.00   1.00    1.00    --   76.00  63.00  71.04   61
 31  ω     29.00 101.00   1.00    1.00    --  113.00 -94.00-180.00   72
 32  ω    121.00 165.00   1.00    1.00    --  113.00  61.00  30.00   44
 33  ω     84.00 113.00   1.00    1.00    --  113.00  61.00  30.00   29
 34  ω     84.00 151.00   1.00    1.00    --  113.00  61.00 -60.00   67
 35  ω     85.00 126.00   1.00    1.00    --  113.00  61.00 120.00   41
 36  ω    133.00 162.00   1.00    1.00    --  113.00  61.00 120.00   29
 37  ω     89.00 145.00   1.00    1.00    --  113.00  45.00 -90.00   56
 38  ω     83.00 177.00   1.00    1.00    --  113.00  61.00  90.00   94
 39  ω    128.00 177.00   1.00    1.00    --  113.00  61.00-180.00   49
 40  ω    117.00 175.00   1.00    1.00    --  113.00  61.00   0.00   58
 41  ω     66.00 109.00   1.00    1.00    --  113.00-111.00 -90.00   43
 42  ω     38.00  91.00   1.00    1.00    --  113.00-111.00 120.00   53
 43  ω     83.00 115.00   1.00    1.00    --  113.00  61.00-180.00   32
 44  ω     85.00 174.00   1.00    1.00    --  113.00  61.00 -30.00   89
 45  ω     83.00 111.00   1.00    1.00    --  113.00  61.00   0.00   28
 46  ω    117.00 155.00   1.00    1.00    --  113.00  61.00-120.00   38
 47  ω     83.00 109.00   1.00    1.00    --  113.00  61.00-120.00   26
 48  ω     87.00 114.00   1.00    1.00    --  113.00  45.00-120.00   27
 49  ω     88.00 113.00   1.00    1.00    --  113.00  45.00 120.00   25
 50  ω     31.00 106.00   1.00    1.00    --  113.00 -94.00   0.00   75
 51  ω    130.00 155.00   1.00    1.00    --  113.00  61.00-150.00   25
 52  ω     86.00 123.00   1.00    1.00    --  113.00  45.00  90.00   37
 53  ω     43.00 116.00   1.00    1.00    --  113.00 -45.00-180.00   73
 54  ω     38.00  86.00   1.00    1.00    --  113.00-111.00  90.00   48
 55  ω     84.00 114.00   1.00    1.00    --  113.00  61.00-150.00   30
 56  ω     83.00 173.00   1.00    1.00    --  113.00  61.00 150.00   90
 57  ω     83.00 178.00   1.00    1.00    --  113.00  61.00 -90.00   95
 58  ω     41.00 107.00   1.00    1.00    --  113.00-111.00 150.00   66
 59  ω     58.00 109.00   1.00    1.00    --  113.00-111.00 -30.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0542213000
_diffrn_orient_matrix_UB_12      0.1064544000
_diffrn_orient_matrix_UB_13      -0.0903432000
_diffrn_orient_matrix_UB_21      -0.0349393000
_diffrn_orient_matrix_UB_22      0.2656187000
_diffrn_orient_matrix_UB_23      0.0252839000
_diffrn_orient_matrix_UB_31      0.1220729000
_diffrn_orient_matrix_UB_32      0.0288217000
_diffrn_orient_matrix_UB_33      0.1012102000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11733
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.261
_diffrn_reflns_theta_min         3.960
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.116a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.109
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1097 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.0092(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2803
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0459
_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/[σ²(Fo²)+(0.0354P)²+0.5545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1123
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_full    0.906
_reflns_Friedel_fraction_max     0.867
_reflns_number_gt                2605
_reflns_number_total             2803
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc06724c7.cif
_cod_data_source_block           (endo-1)(exo-1)_150
_cod_database_code               1577259
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H11 N2 O7'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.54822
 0.45178
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C3(H3), C4(H4), C5(H5), C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C7(H7), C8(H8)
;
_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 1.447
_oxdiff_exptl_absorpt_empirical_full_min 0.716
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5006(4) 0.9113(8) 0.3503(4) 0.0325(10) Uani 1 1 d . . . . .
C9 C 0.5576(6) 0.4142(12) 0.6297(6) 0.0360(16) Uani 1 1 d . . . . .
C10 C 0.6093(6) 0.4028(12) 0.8315(6) 0.0300(14) Uani 1 1 d . . . . .
C11 C 0.5151(6) 0.1617(11) 0.6530(6) 0.0307(14) Uani 1 1 d . . . . .
H11 H 0.550171 0.019738 0.621566 0.037 Uiso 1 1 calc R U . . .
C12 C 0.5466(6) 0.1581(11) 0.7891(6) 0.0284(14) Uani 1 1 d . . . . .
H12 H 0.596676 0.010717 0.827857 0.034 Uiso 1 1 calc R U . . .
C13 C 0.3742(6) 0.1587(12) 0.6098(6) 0.0318(15) Uani 1 1 d . . . . .
H13 H 0.331834 0.214569 0.525487 0.038 Uiso 1 1 calc R U . . .
C14 C 0.4189(6) 0.1548(12) 0.8021(6) 0.0319(15) Uani 1 1 d . . . . .
H14 H 0.416050 0.207286 0.881732 0.038 Uiso 1 1 calc R U . . .
C15 C 0.3403(6) -0.0978(12) 0.6412(7) 0.0358(16) Uani 1 1 d . . . . .
H15 H 0.305527 -0.229723 0.586883 0.043 Uiso 1 1 calc R U . . .
C16 C 0.3685(6) -0.1024(12) 0.7585(6) 0.0336(16) Uani 1 1 d . . . . .
H16 H 0.359135 -0.238121 0.805924 0.040 Uiso 1 1 calc R U . . .
O8 O 0.3540(4) 0.3096(8) 0.7018(4) 0.0344(10) Uani 1 1 d . . . . .
O7 O 0.6507(5) 0.4859(10) 0.9295(5) 0.0411(12) Uani 1 1 d . . . . .
O6 O 0.5506(5) 0.5079(11) 0.5366(5) 0.0492(14) Uani 1 1 d . . . . .
O5 O 0.6090(4) 0.5462(8) 0.7341(4) 0.0345(10) Uani 1 1 d . . . . .
C2 C 0.5996(6) 0.7746(12) 0.3491(6) 0.0328(15) Uani 1 1 d . . . . .
C3 C 0.4225(6) 0.5262(12) 0.2572(6) 0.0312(14) Uani 1 1 d . . . . .
H3 H 0.396187 0.383890 0.296593 0.037 Uiso 1 1 calc R U . . .
C4 C 0.5604(6) 0.5283(12) 0.2875(6) 0.0309(14) Uani 1 1 d . . . . .
H4 H 0.600227 0.384286 0.339606 0.037 Uiso 1 1 calc R U . . .
C5 C 0.3774(7) 0.4975(13) 0.1185(7) 0.0366(17) Uani 1 1 d . . . . .
H5 H 0.293735 0.432849 0.081234 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5684(6) 0.5080(12) 0.1598(6) 0.0319(15) Uani 1 1 d . . . . .
H6 H 0.647818 0.452662 0.157280 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4023(8) 0.7417(14) 0.0701(7) 0.0431(19) Uani 1 1 d . . . . .
H7 H 0.345444 0.865485 0.029717 0.052 Uiso 1 1 calc R U . . .
C8 C 0.5215(8) 0.7495(12) 0.0957(6) 0.0393(17) Uani 1 1 d . . . . .
H8 H 0.566660 0.879594 0.077297 0.047 Uiso 1 1 calc R U . . .
O4 O 0.4705(5) 0.3382(8) 0.1064(5) 0.0395(12) Uani 1 1 d . . . . .
C1 C 0.3958(6) 0.7751(13) 0.3013(6) 0.0351(15) Uani 1 1 d . . . . .
O3 O 0.6982(5) 0.8607(9) 0.3926(5) 0.0428(13) Uani 1 1 d . . . . .
O2 O 0.3019(5) 0.8657(9) 0.2963(6) 0.0496(14) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1 O1 C2 111.1(5) . . ?
O6 C9 C11 129.1(7) . . ?
O6 C9 O5 119.3(6) . . ?
O5 C9 C11 111.6(6) . . ?
O7 C10 C12 130.2(6) . . ?
O7 C10 O5 119.5(6) . . ?
O5 C10 C12 110.2(5) . . ?
C9 C11 H11 113.9 . . ?
C9 C11 C12 103.4(5) . . ?
C9 C11 C13 109.7(5) . . ?
C12 C11 H11 113.9 . . ?
C12 C11 C13 100.8(5) . . ?
C13 C11 H11 113.9 . . ?
C10 C12 C11 104.7(5) . . ?
C10 C12 H12 112.7 . . ?
C10 C12 C14 111.0(5) . . ?
C11 C12 H12 112.7 . . ?
C11 C12 C14 102.3(6) . . ?
C14 C12 H12 112.7 . . ?
C11 C13 H13 115.7 . . ?
C15 C13 C11 105.8(5) . . ?
C15 C13 H13 115.7 . . ?
O8 C13 C11 100.6(5) . . ?
O8 C13 H13 115.7 . . ?
O8 C13 C15 101.1(6) . . ?
C12 C14 H14 116.0 . . ?
C16 C14 C12 104.8(5) . . ?
C16 C14 H14 116.0 . . ?
O8 C14 C12 99.8(5) . . ?
O8 C14 H14 116.0 . . ?
O8 C14 C16 101.8(5) . . ?
C13 C15 H15 126.7 . . ?
C16 C15 C13 106.6(6) . . ?
C16 C15 H15 126.7 . . ?
C14 C16 H16 127.2 . . ?
C15 C16 C14 105.7(6) . . ?
C15 C16 H16 127.2 . . ?
C14 O8 C13 97.1(5) . . ?
C9 O5 C10 109.9(5) . . ?
O1 C2 C4 110.3(5) . . ?
O3 C2 O1 119.9(6) . . ?
O3 C2 C4 129.8(6) . . ?
C4 C3 H3 111.9 . . ?
C4 C3 C5 101.3(5) . . ?
C5 C3 H3 111.9 . . ?
C1 C3 H3 111.9 . . ?
C1 C3 C4 104.2(5) . . ?
C1 C3 C5 114.8(6) . . ?
C2 C4 C3 104.1(5) . . ?
C2 C4 H4 112.0 . . ?
C2 C4 C6 115.0(6) . . ?
C3 C4 H4 112.0 . . ?
C3 C4 C6 100.9(5) . . ?
C6 C4 H4 112.0 . . ?
C3 C5 H5 115.5 . . ?
C7 C5 C3 106.2(6) . . ?
C7 C5 H5 115.5 . . ?
O4 C5 C3 99.7(5) . . ?
O4 C5 H5 115.5 . . ?
O4 C5 C7 102.5(6) . . ?
C4 C6 H6 115.3 . . ?
C8 C6 C4 107.3(5) . . ?
C8 C6 H6 115.3 . . ?
O4 C6 C4 99.3(5) . . ?
O4 C6 H6 115.3 . . ?
O4 C6 C8 102.6(6) . . ?
C5 C7 H7 127.1 . . ?
C8 C7 C5 105.9(7) . . ?
C8 C7 H7 127.1 . . ?
C6 C8 H8 127.3 . . ?
C7 C8 C6 105.3(6) . . ?
C7 C8 H8 127.3 . . ?
C6 O4 C5 96.5(5) . . ?
O1 C1 C3 110.2(5) . . ?
O2 C1 O1 119.6(6) . . ?
O2 C1 C3 130.2(7) . . ?
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
O1 C2 1.390(8) . ?
O1 C1 1.386(9) . ?
C9 C11 1.503(8) . ?
C9 O6 1.193(8) . ?
C9 O5 1.376(9) . ?
C10 C12 1.506(9) . ?
C10 O7 1.185(9) . ?
C10 O5 1.389(8) . ?
C11 H11 1.0000 . ?
C11 C12 1.531(9) . ?
C11 C13 1.573(10) . ?
C12 H12 1.0000 . ?
C12 C14 1.578(9) . ?
C13 H13 1.0000 . ?
C13 C15 1.514(8) . ?
C13 O8 1.446(8) . ?
C14 H14 1.0000 . ?
C14 C16 1.520(9) . ?
C14 O8 1.439(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.318(10) . ?
C16 H16 0.9500 . ?
C2 C4 1.503(9) . ?
C2 O3 1.198(8) . ?
C3 H3 1.0000 . ?
C3 C4 1.552(9) . ?
C3 C5 1.556(10) . ?
C3 C1 1.507(9) . ?
C4 H4 1.0000 . ?
C4 C6 1.559(9) . ?
C5 H5 1.0000 . ?
C5 C7 1.499(11) . ?
C5 O4 1.444(9) . ?
C6 H6 1.0000 . ?
C6 C8 1.507(9) . ?
C6 O4 1.440(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.344(12) . ?
C8 H8 0.9500 . ?
C1 O2 1.199(8) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C4 C3 -3.2(7) . . . . ?
O1 C2 C4 C6 106.3(6) . . . . ?
C9 C11 C12 C10 -2.6(7) . . . . ?
C9 C11 C12 C14 113.2(5) . . . . ?
C9 C11 C13 C15 -177.9(6) . . . . ?
C9 C11 C13 O8 -73.0(6) . . . . ?
C10 C12 C14 C16 -179.0(6) . . . . ?
C10 C12 C14 O8 75.9(6) . . . . ?
C11 C9 O5 C10 1.6(7) . . . . ?
C11 C12 C14 C16 69.7(6) . . . . ?
C11 C12 C14 O8 -35.3(5) . . . . ?
C11 C13 C15 C16 72.6(7) . . . . ?
C11 C13 O8 C14 -59.7(5) . . . . ?
C12 C10 O5 C9 -3.4(7) . . . . ?
C12 C11 C13 C15 -69.2(6) . . . . ?
C12 C11 C13 O8 35.7(5) . . . . ?
C12 C14 C16 C15 -73.0(6) . . . . ?
C12 C14 O8 C13 58.8(5) . . . . ?
C13 C11 C12 C10 -116.1(5) . . . . ?
C13 C11 C12 C14 -0.2(5) . . . . ?
C13 C15 C16 C14 0.9(7) . . . . ?
C15 C13 O8 C14 49.0(6) . . . . ?
C16 C14 O8 C13 -48.7(6) . . . . ?
O8 C13 C15 C16 -31.9(7) . . . . ?
O8 C14 C16 C15 30.7(7) . . . . ?
O7 C10 C12 C11 -179.8(7) . . . . ?
O7 C10 C12 C14 70.6(10) . . . . ?
O7 C10 O5 C9 179.7(7) . . . . ?
O6 C9 C11 C12 -178.1(7) . . . . ?
O6 C9 C11 C13 -71.2(9) . . . . ?
O6 C9 O5 C10 -179.4(6) . . . . ?
O5 C9 C11 C12 0.8(7) . . . . ?
O5 C9 C11 C13 107.7(6) . . . . ?
O5 C10 C12 C11 3.8(7) . . . . ?
O5 C10 C12 C14 -105.9(6) . . . . ?
C2 O1 C1 C3 -2.6(7) . . . . ?
C2 O1 C1 O2 179.6(7) . . . . ?
C2 C4 C6 C8 -42.8(8) . . . . ?
C2 C4 C6 O4 -149.2(5) . . . . ?
C3 C4 C6 C8 68.5(6) . . . . ?
C3 C4 C6 O4 -37.9(6) . . . . ?
C3 C5 C7 C8 73.0(7) . . . . ?
C3 C5 O4 C6 -60.7(6) . . . . ?
C4 C3 C5 C7 -71.1(7) . . . . ?
C4 C3 C5 O4 35.1(6) . . . . ?
C4 C3 C1 O1 0.5(7) . . . . ?
C4 C3 C1 O2 178.0(8) . . . . ?
C4 C6 C8 C7 -72.9(7) . . . . ?
C4 C6 O4 C5 61.7(6) . . . . ?
C5 C3 C4 C2 121.1(5) . . . . ?
C5 C3 C4 C6 1.5(6) . . . . ?
C5 C3 C1 O1 -109.4(7) . . . . ?
C5 C3 C1 O2 68.1(10) . . . . ?
C5 C7 C8 C6 0.1(8) . . . . ?
C7 C5 O4 C6 48.4(7) . . . . ?
C8 C6 O4 C5 -48.4(6) . . . . ?
O4 C5 C7 C8 -31.1(8) . . . . ?
O4 C6 C8 C7 31.1(7) . . . . ?
C1 O1 C2 C4 3.7(7) . . . . ?
C1 O1 C2 O3 -177.0(6) . . . . ?
C1 C3 C4 C2 1.5(7) . . . . ?
C1 C3 C4 C6 -118.0(6) . . . . ?
C1 C3 C5 C7 40.5(8) . . . . ?
C1 C3 C5 O4 146.8(5) . . . . ?
O3 C2 C4 C3 177.6(7) . . . . ?
O3 C2 C4 C6 -72.9(9) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.54822
2 0.45178
