#------------------------------------------------------------------------------
#$Date: 2021-04-30 00:30:21 +0300 (Fri, 30 Apr 2021) $
#$Revision: 264699 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/86/4518637.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_4518637
loop_
_publ_author_name
'Alwaseem, Hanan'
'Giovani, Simone'
'Crotti, Michele'
'Welle, Kevin'
'Jordan, Craig T.'
'Ghaemmaghami, Sina'
'Fasan, Rudi'
_publ_section_title
;
 Comprehensive Structure--Activity Profiling of Micheliolide and its
 Targeted Proteome in Leukemia Cells via Probe-Guided Late-Stage C--H
 Functionalization
;
_journal_name_full               'ACS Central Science'
_journal_paper_doi               10.1021/acscentsci.0c01624
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H20 O4'
_chemical_formula_sum            'C15 H20 O4'
_chemical_formula_weight         264.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-09-25
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.39540(10)
_cell_length_b                   15.0420(2)
_cell_length_c                   16.9395(3)
_cell_measurement_reflns_used    12058
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.6200
_cell_measurement_theta_min      5.1630
_cell_volume                     2648.79(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -86.00   1.00   0.50    0.06    --  -49.62 111.00-111.00  174
  2  ω     21.00  88.00   0.50    0.06    --   49.62-111.00 154.00  134
  3  ω   -156.00 -78.00   0.50    0.22    --  -84.25-111.00 154.00  156
  4  ω    -85.00 -12.00   0.50    0.22    --  -84.25 111.00-111.00  146
  5  ω     34.00 111.00   0.50    0.22    --  105.75-111.00 154.00  154
  6  ω    100.00 178.00   0.50    0.22    --  105.75 111.00-111.00  156
  7  ω    -57.00  22.00   0.50    0.06    --  -49.62  38.00 -60.00  158
  8  ω   -121.00 -70.00   0.50    0.06    --  -49.62-125.00 -60.00  102
  9  ω     31.00  95.00   0.50    0.06    --   49.62-125.00 120.00  128
 10  ω     33.00  82.00   0.50    0.22    --  105.75 -15.00-180.00   98
 11  ω     34.00  72.00   0.50    0.22    --  105.75 -30.00-180.00   76
 12  ω     34.00  72.00   0.50    0.22    --  105.75 -30.00  90.00   76
 13  ω     98.00 178.00   0.50    0.22    --  105.75  30.00 -30.00  160
 14  ω     34.00  72.00   0.50    0.22    --  105.75 -30.00 -30.00   76
 15  ω     34.00  90.00   0.50    0.22    --  105.75 -45.00  30.00  112
 16  ω     34.00  90.00   0.50    0.22    --  105.75 -45.00-120.00  112
 17  ω     34.00  90.00   0.50    0.22    --  105.75 -45.00-180.00  112
 18  ω     34.00  90.00   0.50    0.22    --  105.75 -45.00 -30.00  112
 19  ω     34.00  90.00   0.50    0.22    --  105.75 -45.00 150.00  112
 20  ω     99.00 176.00   0.50    0.22    --  105.75  15.00 120.00  154
 21  ω    101.00 152.00   0.50    0.22    --  105.75  45.00 -90.00  102
 22  ω     46.00  72.00   0.50    0.22    --  105.75 -45.00   0.00   52
 23  ω     38.00  64.00   0.50    0.22    --  105.75 -15.00 -90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0143792000
_diffrn_orient_matrix_UB_12      -0.0410763000
_diffrn_orient_matrix_UB_13      0.0828475000
_diffrn_orient_matrix_UB_21      0.0980478000
_diffrn_orient_matrix_UB_22      0.0673104000
_diffrn_orient_matrix_UB_23      0.0327817000
_diffrn_orient_matrix_UB_31      -0.1101744000
_diffrn_orient_matrix_UB_32      0.0653317000
_diffrn_orient_matrix_UB_33      0.0183435000
_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  0.0347
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13923
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        74.504
_diffrn_reflns_theta_max         77.864
_diffrn_reflns_theta_min         5.172
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (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    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.154
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       0.00059(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   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0308
_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)+(0.0425P)²+1.0692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                2748
_reflns_number_total             2792
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            oc0c01624_si_001.cif
_cod_data_source_block           fasha01
_cod_database_code               4518637
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.890
_shelx_estimated_absorpt_t_min   0.767
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8(2)
 0.2(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
3. Others
 Fixed Sof: H3A(0.5) H3B(0.5) H4A(0.5) H4B(0.5)
4.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3C,H3D), C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B)
4.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_olex2_submission_original_sample_id fasha01
_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 3.764
_oxdiff_exptl_absorpt_empirical_full_min 0.564
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_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 0.44824(11) 0.39489(8) 0.36953(8) 0.0207(3) Uani 1 1 d . . . . .
O2 O 0.66193(12) 0.41577(9) 0.37009(10) 0.0290(3) Uani 1 1 d . . . . .
O3 O -0.02741(14) 0.08399(10) 0.44455(9) 0.0303(3) Uani 1 1 d . . . . .
H3A H 0.031(6) 0.037(4) 0.460(4) 0.046 Uiso 0.5 1 d . U P A 1
H3B H -0.087(6) 0.046(4) 0.431(4) 0.046 Uiso 0.5 1 d . U P B 2
O4 O 0.22033(14) 0.50557(8) 0.42028(8) 0.0217(3) Uani 1 1 d . . . . .
H4A H 0.298(6) 0.507(4) 0.415(3) 0.033 Uiso 0.5 1 d . U P C 1
H4B H 0.217(5) 0.500(4) 0.472(3) 0.033 Uiso 0.5 1 d . U P D 2
C1 C 0.13157(16) 0.27020(12) 0.39281(10) 0.0188(4) Uani 1 1 d . . . . .
C2 C 0.00534(16) 0.31823(11) 0.37516(11) 0.0205(3) Uani 1 1 d . . . . .
H2A H -0.016003 0.314495 0.318296 0.025 Uiso 1 1 calc R U . . .
H2B H -0.066253 0.292332 0.406082 0.025 Uiso 1 1 calc R U . . .
C3 C 0.03019(16) 0.41439(12) 0.39966(12) 0.0218(4) Uani 1 1 d . . . . .
H3C H 0.015177 0.422578 0.456908 0.026 Uiso 1 1 calc R U . . .
H3D H -0.026070 0.455731 0.370058 0.026 Uiso 1 1 calc R U . . .
C4 C 0.17207(16) 0.42975(11) 0.37890(11) 0.0192(4) Uani 1 1 d . . . . .
C5 C 0.23464(16) 0.34109(11) 0.40694(10) 0.0174(3) Uani 1 1 d . . . . .
H5 H 0.250366 0.345367 0.465054 0.021 Uiso 1 1 calc R U . . .
C6 C 0.36073(16) 0.31840(11) 0.36696(10) 0.0182(3) Uani 1 1 d . . . . .
H6 H 0.343372 0.302827 0.310570 0.022 Uiso 1 1 calc R U . . .
C7 C 0.43714(16) 0.24307(11) 0.40507(11) 0.0195(3) Uani 1 1 d . . . . .
H7 H 0.432431 0.250841 0.463630 0.023 Uiso 1 1 calc R U . . .
C8 C 0.38800(17) 0.15064(11) 0.38550(12) 0.0235(4) Uani 1 1 d . . . . .
H8A H 0.452699 0.106112 0.402115 0.028 Uiso 1 1 calc R U . . .
H8B H 0.376780 0.145379 0.327653 0.028 Uiso 1 1 calc R U . . .
C9 C 0.25996(17) 0.13055(11) 0.42631(13) 0.0253(4) Uani 1 1 d . . . . .
H9A H 0.242078 0.066244 0.420413 0.030 Uiso 1 1 calc R U . . .
H9B H 0.270331 0.142560 0.483418 0.030 Uiso 1 1 calc R U . . .
C10 C 0.14278(16) 0.18168(12) 0.39726(11) 0.0213(4) Uani 1 1 d . . . . .
C11 C 0.57105(17) 0.26683(11) 0.37917(11) 0.0214(4) Uani 1 1 d . . . . .
C12 C 0.57164(17) 0.36595(11) 0.37247(11) 0.0219(4) Uani 1 1 d . . . . .
C13 C 0.67093(18) 0.21679(14) 0.36044(13) 0.0285(4) Uani 1 1 d . . . . .
H13A H 0.749(3) 0.2451(18) 0.3430(16) 0.036(7) Uiso 1 1 d . . . . .
H13B H 0.664(2) 0.1520(17) 0.3655(16) 0.029(6) Uiso 1 1 d . . . . .
C14 C 0.03049(17) 0.12294(12) 0.37548(12) 0.0233(4) Uani 1 1 d . . . . .
H14A H -0.034652 0.158537 0.346872 0.028 Uiso 1 1 calc R U . . .
H14B H 0.060399 0.075098 0.339783 0.028 Uiso 1 1 calc R U . . .
C15 C 0.18865(18) 0.44769(12) 0.29126(11) 0.0238(4) Uani 1 1 d . . . . .
H15A H 0.136762 0.499368 0.276178 0.036 Uiso 1 1 calc R U . . .
H15B H 0.160420 0.395619 0.261115 0.036 Uiso 1 1 calc R U . . .
H15C H 0.279457 0.459668 0.279934 0.036 Uiso 1 1 calc R U . . .
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
C12 O1 C6 109.64(12) . . ?
C14 O3 H3A 104(4) . . ?
C14 O3 H3B 110(4) . . ?
C4 O4 H4A 108(4) . . ?
C4 O4 H4B 113(4) . . ?
C2 C1 C5 107.61(13) . . ?
C10 C1 C2 123.79(15) . . ?
C10 C1 C5 128.55(16) . . ?
C1 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 C1 104.45(14) . . ?
C3 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C2 C3 H3C 110.9 . . ?
C2 C3 H3D 110.9 . . ?
C2 C3 C4 104.07(14) . . ?
H3C C3 H3D 109.0 . . ?
C4 C3 H3C 110.9 . . ?
C4 C3 H3D 110.9 . . ?
O4 C4 C3 110.20(14) . . ?
O4 C4 C5 112.77(14) . . ?
O4 C4 C15 107.31(14) . . ?
C3 C4 C5 101.69(13) . . ?
C15 C4 C3 111.10(15) . . ?
C15 C4 C5 113.75(14) . . ?
C1 C5 C4 104.86(13) . . ?
C1 C5 H5 108.3 . . ?
C4 C5 H5 108.3 . . ?
C6 C5 C1 112.27(14) . . ?
C6 C5 C4 114.71(14) . . ?
C6 C5 H5 108.3 . . ?
O1 C6 C5 110.29(13) . . ?
O1 C6 H6 108.9 . . ?
O1 C6 C7 104.29(13) . . ?
C5 C6 H6 108.9 . . ?
C5 C6 C7 115.37(14) . . ?
C7 C6 H6 108.9 . . ?
C6 C7 H7 107.9 . . ?
C8 C7 C6 114.35(15) . . ?
C8 C7 H7 107.9 . . ?
C11 C7 C6 100.48(13) . . ?
C11 C7 H7 107.9 . . ?
C11 C7 C8 117.76(15) . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C7 C8 C9 112.02(15) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C8 C9 H9A 108.1 . . ?
C8 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?
C10 C9 C8 116.76(15) . . ?
C10 C9 H9A 108.1 . . ?
C10 C9 H9B 108.1 . . ?
C1 C10 C9 126.18(16) . . ?
C1 C10 C14 120.07(16) . . ?
C14 C10 C9 113.70(15) . . ?
C12 C11 C7 105.26(15) . . ?
C13 C11 C7 131.51(16) . . ?
C13 C11 C12 123.14(17) . . ?
O1 C12 C11 108.60(14) . . ?
O2 C12 O1 122.53(15) . . ?
O2 C12 C11 128.87(17) . . ?
C11 C13 H13A 118.8(16) . . ?
C11 C13 H13B 119.4(14) . . ?
H13A C13 H13B 122(2) . . ?
O3 C14 C10 111.26(16) . . ?
O3 C14 H14A 109.4 . . ?
O3 C14 H14B 109.4 . . ?
C10 C14 H14A 109.4 . . ?
C10 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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 C6 1.4673(19) . ?
O1 C12 1.356(2) . ?
O2 C12 1.202(2) . ?
O3 H3A 0.97(6) . ?
O3 H3B 0.87(7) . ?
O3 C14 1.440(2) . ?
O4 H4A 0.81(6) . ?
O4 H4B 0.88(5) . ?
O4 C4 1.430(2) . ?
C1 C2 1.527(2) . ?
C1 C5 1.530(2) . ?
C1 C10 1.339(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.527(2) . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C3 C4 1.534(2) . ?
C4 C5 1.558(2) . ?
C4 C15 1.519(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.514(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.527(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.518(2) . ?
C7 C11 1.503(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.530(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.522(2) . ?
C10 C14 1.510(2) . ?
C11 C12 1.495(2) . ?
C11 C13 1.321(3) . ?
C13 H13A 0.96(3) . ?
C13 H13B 0.98(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3A O3 0.97(6) 2.51(6) 3.149(3) 123(4) 4_556 yes
O3 H3B O1 0.87(7) 2.53(6) 3.1258(19) 126(5) 5_445 yes
O3 H3B O4 0.87(7) 2.10(7) 2.905(2) 153(5) 5_445 yes
O4 H4A O1 0.81(6) 2.42(6) 3.0206(18) 131(5) . yes
O4 H4A O3 0.81(6) 2.21(6) 2.905(2) 143(5) 5 yes
O4 H4B O4 0.88(5) 1.83(5) 2.706(3) 175(5) 4_566 yes
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 C6 C7 C8 -160.37(14) . . . . ?
O1 C6 C7 C11 -33.23(16) . . . . ?
O4 C4 C5 C1 150.93(14) . . . . ?
O4 C4 C5 C6 -85.45(18) . . . . ?
C1 C2 C3 C4 34.87(18) . . . . ?
C1 C5 C6 O1 169.52(13) . . . . ?
C1 C5 C6 C7 -72.67(19) . . . . ?
C1 C10 C14 O3 -106.7(2) . . . . ?
C2 C1 C5 C4 -12.11(18) . . . . ?
C2 C1 C5 C6 -137.28(15) . . . . ?
C2 C1 C10 C9 -170.34(17) . . . . ?
C2 C1 C10 C14 7.0(3) . . . . ?
C2 C3 C4 O4 -161.74(14) . . . . ?
C2 C3 C4 C5 -41.92(17) . . . . ?
C2 C3 C4 C15 79.45(17) . . . . ?
C3 C4 C5 C1 32.94(17) . . . . ?
C3 C4 C5 C6 156.57(14) . . . . ?
C4 C5 C6 O1 49.96(19) . . . . ?
C4 C5 C6 C7 167.76(14) . . . . ?
C5 C1 C2 C3 -13.76(19) . . . . ?
C5 C1 C10 C9 6.9(3) . . . . ?
C5 C1 C10 C14 -175.81(16) . . . . ?
C5 C6 C7 C8 78.52(19) . . . . ?
C5 C6 C7 C11 -154.35(15) . . . . ?
C6 O1 C12 O2 175.33(19) . . . . ?
C6 O1 C12 C11 -4.93(19) . . . . ?
C6 C7 C8 C9 -71.4(2) . . . . ?
C6 C7 C11 C12 30.46(18) . . . . ?
C6 C7 C11 C13 -145.9(2) . . . . ?
C7 C8 C9 C10 69.4(2) . . . . ?
C7 C11 C12 O1 -17.2(2) . . . . ?
C7 C11 C12 O2 162.5(2) . . . . ?
C8 C7 C11 C12 155.30(16) . . . . ?
C8 C7 C11 C13 -21.0(3) . . . . ?
C8 C9 C10 C1 -55.1(3) . . . . ?
C8 C9 C10 C14 127.42(17) . . . . ?
C9 C10 C14 O3 70.9(2) . . . . ?
C10 C1 C2 C3 163.96(18) . . . . ?
C10 C1 C5 C4 170.31(18) . . . . ?
C10 C1 C5 C6 45.1(3) . . . . ?
C11 C7 C8 C9 170.97(15) . . . . ?
C12 O1 C6 C5 149.16(15) . . . . ?
C12 O1 C6 C7 24.73(18) . . . . ?
C13 C11 C12 O1 159.53(18) . . . . ?
C13 C11 C12 O2 -20.8(3) . . . . ?
C15 C4 C5 C1 -86.57(17) . . . . ?
C15 C4 C5 C6 37.1(2) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(2)
2 0.2(2)
