#------------------------------------------------------------------------------
#$Date: 2022-03-18 03:38:43 +0200 (Fri, 18 Mar 2022) $
#$Revision: 273768 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158575.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_7158575
loop_
_publ_author_name
'Yang, Haidi'
'Liu, Jinyao'
'Hu, Pan'
'Gao, Liang'
'Huang, Zedu'
'Chen, Fen-Er'
_publ_section_title
;
 Asymmetric Total Synthesis of
 (+)-(2R,4’R,8’R)--Tocopherol Enabled by Enzymatic
 Desymmetrization
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00384H
_journal_year                    2022
_chemical_formula_sum            'C14 H20 O3'
_chemical_formula_weight         236.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-10-12 deposited with the CCDC.	2022-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.5260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   38.9060(12)
_cell_length_b                   5.7838(2)
_cell_length_c                   11.1782(3)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      59.43
_cell_measurement_theta_min      3.52
_cell_volume                     2455.50(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16142
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         58.993
_diffrn_reflns_theta_min         3.664
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_correction_T_min  0.579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       sheet
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
; 
 Flack x determined using 2036 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.14(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5341
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0751P)²+0.5608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1270
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                4979
_reflns_number_total             5341
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00384h2.cif
_cod_data_source_block           ga_210601b_b
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7158575
_shelx_shelxl_version_number     2016/6
_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_min   0.829
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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 0.59257(4) 0.6543(3) 0.72413(13) 0.0260(4) Uani 1 1 d . . . . .
O2 O 0.73216(4) 0.8027(4) 0.94347(15) 0.0322(4) Uani 1 1 d D . . . .
H2 H 0.7368(10) 0.941(6) 0.972(3) 0.063(12) Uiso 1 1 d D . . . .
O3 O 0.52382(4) 0.4918(4) 0.64713(15) 0.0349(4) Uani 1 1 d D . . . .
H3 H 0.5361(8) 0.441(6) 0.603(3) 0.040(8) Uiso 1 1 d D . . . .
C1 C 0.56484(5) 0.7623(4) 0.7716(2) 0.0257(5) Uani 1 1 d . . . . .
C2 C 0.57323(6) 1.0183(5) 0.7915(2) 0.0334(6) Uani 1 1 d . . . . .
H2A H 0.553814 1.095836 0.820242 0.040 Uiso 1 1 calc R U . . .
H2B H 0.575185 1.090040 0.712813 0.040 Uiso 1 1 calc R U . . .
C3 C 0.60763(6) 1.0529(4) 0.8857(2) 0.0280(5) Uani 1 1 d . . . . .
H3A H 0.615597 1.214928 0.882452 0.034 Uiso 1 1 calc R U . . .
H3B H 0.603643 1.023782 0.968913 0.034 Uiso 1 1 calc R U . . .
C4 C 0.63587(5) 0.8912(4) 0.86114(19) 0.0208(4) Uani 1 1 d . . . . .
C5 C 0.67128(5) 0.9251(4) 0.91833(18) 0.0217(5) Uani 1 1 d . . . . .
C6 C 0.69679(5) 0.7804(5) 0.88811(17) 0.0226(4) Uani 1 1 d . . . . .
C7 C 0.68796(5) 0.6019(4) 0.80224(17) 0.0215(4) Uani 1 1 d . . . . .
C8 C 0.65267(5) 0.5608(4) 0.75008(17) 0.0205(4) Uani 1 1 d . . . . .
C9 C 0.62691(5) 0.7062(4) 0.78061(17) 0.0197(4) Uani 1 1 d . . . . .
C10 C 0.68160(6) 1.1145(5) 1.0122(2) 0.0304(5) Uani 1 1 d . . . . .
H10A H 0.683212 1.261658 0.970275 0.046 Uiso 1 1 calc R U . . .
H10B H 0.704485 1.077827 1.065230 0.046 Uiso 1 1 calc R U . . .
H10C H 0.663809 1.126961 1.061896 0.046 Uiso 1 1 calc R U . . .
C11 C 0.71638(6) 0.4566(5) 0.7665(2) 0.0304(5) Uani 1 1 d . . . . .
H11A H 0.738902 0.538911 0.787703 0.046 Uiso 1 1 calc R U . . .
H11B H 0.710345 0.427633 0.678015 0.046 Uiso 1 1 calc R U . . .
H11C H 0.718341 0.309041 0.810514 0.046 Uiso 1 1 calc R U . . .
C12 C 0.64206(6) 0.3682(5) 0.65923(19) 0.0274(5) Uani 1 1 d . . . . .
H12A H 0.616390 0.351322 0.640849 0.041 Uiso 1 1 calc R U . . .
H12B H 0.653003 0.223500 0.693932 0.041 Uiso 1 1 calc R U . . .
H12C H 0.649883 0.404224 0.583688 0.041 Uiso 1 1 calc R U . . .
C13 C 0.53219(6) 0.7287(5) 0.6703(2) 0.0351(6) Uani 1 1 d . . . . .
H13A H 0.512005 0.807249 0.693629 0.042 Uiso 1 1 calc R U . . .
H13B H 0.536044 0.801865 0.594226 0.042 Uiso 1 1 calc R U . . .
C14 C 0.56084(6) 0.6403(5) 0.8885(2) 0.0306(5) Uani 1 1 d . . . . .
H14A H 0.553235 0.480489 0.869425 0.046 Uiso 1 1 calc R U . . .
H14B H 0.543231 0.721306 0.923642 0.046 Uiso 1 1 calc R U . . .
H14C H 0.583493 0.640665 0.947566 0.046 Uiso 1 1 calc R U . . .
O4 O 0.40491(4) 0.3411(3) 0.78681(13) 0.0265(4) Uani 1 1 d . . . . .
O5 O 0.26643(4) 0.1911(4) 0.55492(15) 0.0353(5) Uani 1 1 d D . . . .
H5 H 0.2636(10) 0.058(6) 0.517(3) 0.066(13) Uiso 1 1 d D . . . .
O6 O 0.45996(4) 0.2907(3) 0.55996(14) 0.0323(4) Uani 1 1 d D . . . .
H6 H 0.4805(8) 0.334(7) 0.594(3) 0.060(10) Uiso 1 1 d D . . . .
C15 C 0.43322(5) 0.2418(4) 0.73895(19) 0.0233(5) Uani 1 1 d . . . . .
C16 C 0.42602(6) -0.0106(5) 0.7102(2) 0.0290(5) Uani 1 1 d . . . . .
H16A H 0.424854 -0.094196 0.786499 0.035 Uiso 1 1 calc R U . . .
H16B H 0.445653 -0.076879 0.677918 0.035 Uiso 1 1 calc R U . . .
C17 C 0.39157(5) -0.0456(4) 0.6163(2) 0.0263(5) Uani 1 1 d . . . . .
H17A H 0.395398 -0.012349 0.533320 0.032 Uiso 1 1 calc R U . . .
H17B H 0.384120 -0.209038 0.618068 0.032 Uiso 1 1 calc R U . . .
C18 C 0.36270(5) 0.1096(4) 0.64190(18) 0.0199(4) Uani 1 1 d . . . . .
C19 C 0.32754(5) 0.0733(4) 0.58184(18) 0.0209(4) Uani 1 1 d . . . . .
C20 C 0.30166(5) 0.2156(4) 0.61173(17) 0.0225(5) Uani 1 1 d . . . . .
C21 C 0.30972(5) 0.3922(4) 0.69786(18) 0.0232(5) Uani 1 1 d . . . . .
C22 C 0.34493(5) 0.4351(4) 0.75280(17) 0.0207(4) Uani 1 1 d . . . . .
C23 C 0.37085(5) 0.2918(4) 0.72451(17) 0.0200(4) Uani 1 1 d . . . . .
C24 C 0.31824(6) -0.1128(5) 0.4866(2) 0.0293(5) Uani 1 1 d . . . . .
H24A H 0.313563 -0.257413 0.525862 0.044 Uiso 1 1 calc R U . . .
H24B H 0.337889 -0.135485 0.445810 0.044 Uiso 1 1 calc R U . . .
H24C H 0.297192 -0.066858 0.425862 0.044 Uiso 1 1 calc R U . . .
C25 C 0.28088(6) 0.5355(5) 0.7320(2) 0.0317(6) Uani 1 1 d . . . . .
H25A H 0.279428 0.685205 0.690089 0.047 Uiso 1 1 calc R U . . .
H25B H 0.286120 0.560202 0.820823 0.047 Uiso 1 1 calc R U . . .
H25C H 0.258351 0.454263 0.707181 0.047 Uiso 1 1 calc R U . . .
C26 C 0.35494(6) 0.6301(5) 0.8431(2) 0.0292(5) Uani 1 1 d . . . . .
H26A H 0.341839 0.769700 0.811032 0.044 Uiso 1 1 calc R U . . .
H26B H 0.380258 0.660094 0.855543 0.044 Uiso 1 1 calc R U . . .
H26C H 0.349221 0.587400 0.921342 0.044 Uiso 1 1 calc R U . . .
C27 C 0.43546(5) 0.3830(4) 0.6251(2) 0.0252(5) Uani 1 1 d . . . . .
H27A H 0.411873 0.388693 0.569760 0.030 Uiso 1 1 calc R U . . .
H27B H 0.442405 0.543432 0.650303 0.030 Uiso 1 1 calc R U . . .
C28 C 0.46591(6) 0.2767(6) 0.8403(2) 0.0373(6) Uani 1 1 d . . . . .
H28A H 0.467678 0.439652 0.864945 0.056 Uiso 1 1 calc R U . . .
H28B H 0.486859 0.232695 0.810266 0.056 Uiso 1 1 calc R U . . .
H28C H 0.464243 0.180344 0.910916 0.056 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 0.0137 0.0067 '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 0.0389 0.0241 '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
C9 O1 C1 117.63(16) . . ?
C6 O2 H2 111(3) . . ?
C13 O3 H3 108(2) . . ?
O1 C1 C13 103.94(18) . . ?
O1 C1 C14 109.79(19) . . ?
C13 C1 C14 110.8(2) . . ?
O1 C1 C2 108.73(19) . . ?
C13 C1 C2 110.6(2) . . ?
C14 C1 C2 112.6(2) . . ?
C1 C2 C3 110.9(2) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 110.9(2) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C9 C4 C5 119.07(19) . . ?
C9 C4 C3 120.17(18) . . ?
C5 C4 C3 120.8(2) . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 C10 120.51(19) . . ?
C4 C5 C10 120.4(2) . . ?
O2 C6 C5 121.7(2) . . ?
O2 C6 C7 116.52(19) . . ?
C5 C6 C7 121.77(18) . . ?
C8 C7 C6 119.09(19) . . ?
C8 C7 C11 120.5(2) . . ?
C6 C7 C11 120.44(19) . . ?
C7 C8 C9 119.2(2) . . ?
C7 C8 C12 120.73(19) . . ?
C9 C8 C12 120.09(18) . . ?
O1 C9 C4 122.95(18) . . ?
O1 C9 C8 115.41(19) . . ?
C4 C9 C8 121.63(18) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 C1 112.4(2) . . ?
O3 C13 H13A 109.1 . . ?
C1 C13 H13A 109.1 . . ?
O3 C13 H13B 109.1 . . ?
C1 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C23 O4 C15 117.06(15) . . ?
C20 O5 H5 109(2) . . ?
C27 O6 H6 109(3) . . ?
O4 C15 C16 110.04(19) . . ?
O4 C15 C28 104.65(18) . . ?
C16 C15 C28 112.0(2) . . ?
O4 C15 C27 106.34(17) . . ?
C16 C15 C27 112.39(19) . . ?
C28 C15 C27 111.0(2) . . ?
C15 C16 C17 111.7(2) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C16 111.63(19) . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C23 C18 C19 119.29(19) . . ?
C23 C18 C17 120.21(17) . . ?
C19 C18 C17 120.5(2) . . ?
C20 C19 C18 118.4(2) . . ?
C20 C19 C24 121.12(18) . . ?
C18 C19 C24 120.44(19) . . ?
O5 C20 C21 116.33(19) . . ?
O5 C20 C19 121.5(2) . . ?
C21 C20 C19 122.16(18) . . ?
C20 C21 C22 119.14(19) . . ?
C20 C21 C25 120.64(19) . . ?
C22 C21 C25 120.2(2) . . ?
C23 C22 C21 118.9(2) . . ?
C23 C22 C26 120.15(19) . . ?
C21 C22 C26 120.92(19) . . ?
O4 C23 C18 122.98(18) . . ?
O4 C23 C22 115.07(19) . . ?
C18 C23 C22 121.93(18) . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O6 C27 C15 112.99(18) . . ?
O6 C27 H27A 109.0 . . ?
C15 C27 H27A 109.0 . . ?
O6 C27 H27B 109.0 . . ?
C15 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
C15 C28 H28A 109.5 . . ?
C15 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C15 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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 C9 1.381(2) . ?
O1 C1 1.444(3) . ?
O2 C6 1.387(2) . ?
O2 H2 0.87(3) . ?
O3 C13 1.419(4) . ?
O3 H3 0.82(3) . ?
C1 C13 1.520(3) . ?
C1 C14 1.522(3) . ?
C1 C2 1.522(4) . ?
C2 C3 1.526(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.513(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C9 1.393(3) . ?
C4 C5 1.401(3) . ?
C5 C6 1.395(3) . ?
C5 C10 1.510(3) . ?
C6 C7 1.401(3) . ?
C7 C8 1.391(3) . ?
C7 C11 1.510(3) . ?
C8 C9 1.406(3) . ?
C8 C12 1.504(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O4 C23 1.386(2) . ?
O4 C15 1.444(2) . ?
O5 C20 1.387(2) . ?
O5 H5 0.88(3) . ?
O6 C27 1.423(3) . ?
O6 H6 0.84(3) . ?
C15 C16 1.508(4) . ?
C15 C28 1.522(3) . ?
C15 C27 1.530(3) . ?
C16 C17 1.526(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.513(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C23 1.392(3) . ?
C18 C19 1.403(3) . ?
C19 C20 1.396(3) . ?
C19 C24 1.502(3) . ?
C20 C21 1.392(3) . ?
C21 C22 1.397(3) . ?
C21 C25 1.509(3) . ?
C22 C23 1.394(3) . ?
C22 C26 1.507(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
O6 H6 O3 0.84(3) 1.90(3) 2.725(2) 167(4) .
O5 H5 O5 0.88(3) 2.47(3) 3.2899(15) 156(3) 4_546
O3 H3 O6 0.82(3) 2.05(3) 2.783(2) 149(3) 2_656
O2 H2 O2 0.87(3) 2.50(3) 3.3356(15) 163(3) 4_657
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
C9 O1 C1 C13 163.8(2) . . . . ?
C9 O1 C1 C14 -77.6(2) . . . . ?
C9 O1 C1 C2 46.0(2) . . . . ?
O1 C1 C2 C3 -61.9(3) . . . . ?
C13 C1 C2 C3 -175.38(19) . . . . ?
C14 C1 C2 C3 60.0(3) . . . . ?
C1 C2 C3 C4 45.3(3) . . . . ?
C2 C3 C4 C9 -13.7(3) . . . . ?
C2 C3 C4 C5 166.1(2) . . . . ?
C9 C4 C5 C6 3.4(3) . . . . ?
C3 C4 C5 C6 -176.36(19) . . . . ?
C9 C4 C5 C10 -176.08(19) . . . . ?
C3 C4 C5 C10 4.1(3) . . . . ?
C4 C5 C6 O2 -178.7(2) . . . . ?
C10 C5 C6 O2 0.8(3) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C10 C5 C6 C7 179.4(2) . . . . ?
O2 C6 C7 C8 175.55(19) . . . . ?
C5 C6 C7 C8 -3.1(3) . . . . ?
O2 C6 C7 C11 -4.7(3) . . . . ?
C5 C6 C7 C11 176.7(2) . . . . ?
C6 C7 C8 C9 2.9(3) . . . . ?
C11 C7 C8 C9 -176.87(19) . . . . ?
C6 C7 C8 C12 -178.92(19) . . . . ?
C11 C7 C8 C12 1.3(3) . . . . ?
C1 O1 C9 C4 -14.4(3) . . . . ?
C1 O1 C9 C8 166.46(18) . . . . ?
C5 C4 C9 O1 177.28(18) . . . . ?
C3 C4 C9 O1 -2.9(3) . . . . ?
C5 C4 C9 C8 -3.6(3) . . . . ?
C3 C4 C9 C8 176.15(19) . . . . ?
C7 C8 C9 O1 179.57(18) . . . . ?
C12 C8 C9 O1 1.4(3) . . . . ?
C7 C8 C9 C4 0.4(3) . . . . ?
C12 C8 C9 C4 -177.75(19) . . . . ?
O1 C1 C13 O3 62.3(3) . . . . ?
C14 C1 C13 O3 -55.6(3) . . . . ?
C2 C1 C13 O3 178.8(2) . . . . ?
C23 O4 C15 C16 -46.6(2) . . . . ?
C23 O4 C15 C28 -167.0(2) . . . . ?
C23 O4 C15 C27 75.4(2) . . . . ?
O4 C15 C16 C17 59.3(2) . . . . ?
C28 C15 C16 C17 175.19(17) . . . . ?
C27 C15 C16 C17 -59.0(2) . . . . ?
C15 C16 C17 C18 -42.2(3) . . . . ?
C16 C17 C18 C23 13.2(3) . . . . ?
C16 C17 C18 C19 -167.45(19) . . . . ?
C23 C18 C19 C20 -3.0(3) . . . . ?
C17 C18 C19 C20 177.67(18) . . . . ?
C23 C18 C19 C24 176.24(19) . . . . ?
C17 C18 C19 C24 -3.1(3) . . . . ?
C18 C19 C20 O5 179.24(19) . . . . ?
C24 C19 C20 O5 0.0(3) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
C24 C19 C20 C21 -178.6(2) . . . . ?
O5 C20 C21 C22 -176.09(19) . . . . ?
C19 C20 C21 C22 2.6(3) . . . . ?
O5 C20 C21 C25 4.1(3) . . . . ?
C19 C20 C21 C25 -177.2(2) . . . . ?
C20 C21 C22 C23 -3.3(3) . . . . ?
C25 C21 C22 C23 176.50(19) . . . . ?
C20 C21 C22 C26 177.76(19) . . . . ?
C25 C21 C22 C26 -2.4(3) . . . . ?
C15 O4 C23 C18 17.5(3) . . . . ?
C15 O4 C23 C22 -164.04(18) . . . . ?
C19 C18 C23 O4 -179.39(19) . . . . ?
C17 C18 C23 O4 0.0(3) . . . . ?
C19 C18 C23 C22 2.3(3) . . . . ?
C17 C18 C23 C22 -178.39(19) . . . . ?
C21 C22 C23 O4 -177.51(18) . . . . ?
C26 C22 C23 O4 1.4(3) . . . . ?
C21 C22 C23 C18 0.9(3) . . . . ?
C26 C22 C23 C18 179.84(19) . . . . ?
O4 C15 C27 O6 -173.90(16) . . . . ?
C16 C15 C27 O6 -53.4(2) . . . . ?
C28 C15 C27 O6 72.8(3) . . . . ?
