# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ga_210601b_b
_database_code_depnum_ccdc_archive 'CCDC 2115175'
loop_
_audit_author_name
_audit_author_address
'Haidi Yang '
;Fudan university
China
;
_audit_update_record             
;
2021-10-12 deposited with the CCDC.	2022-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 O3'
_chemical_formula_weight         236.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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. 
;

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'

_cell_length_a                   38.9060(12)
_cell_length_b                   5.7838(2)
_cell_length_c                   11.1782(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.5260(10)
_cell_angle_gamma                90
_cell_volume                     2455.50(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      59.43

_exptl_crystal_description       sheet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.453
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.579
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16142
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.664
_diffrn_reflns_theta_max         58.993
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5341
_reflns_number_gt                4979
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.985

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0751P)²+0.5608P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_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)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5341
_refine_ls_number_parameters     331
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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_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_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) . . . . ?

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

_refine_diff_density_max         0.570
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.069

