# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_034592_wxx_160k_2_d
_database_code_depnum_ccdc_archive 'CCDC 2016127'
loop_
_audit_author_name
_audit_author_address
'Jun Xu'
;Tianjing University
China
;
_audit_update_record             
;
2020-07-14 deposited with the CCDC.	2020-11-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_034592_wxx_160k_2_d 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Author Response: This alert is due to low quality crystals that were weakly diffracting. The data were only collected to 0.92 \%A.
;
# Added during the CSD deposition process: Tuesday 14 July 2020 03:16 AM
# end Validation Reply Form

_audit_creation_date             2020-07-10
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.05.07 svn.rd67b107b for OlexSys, GUI svn.r6105)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 O6, C4 H8 O2'
_chemical_formula_sum            'C25 H28 O8'
_chemical_formula_weight         456.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H28 O8'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   24.3727(11)
_cell_length_b                   5.3458(2)
_cell_length_c                   36.3946(17)
_cell_angle_alpha                90
_cell_angle_beta                 106.501(5)
_cell_angle_gamma                90
_cell_volume                     4546.6(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2303
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      53.3220
_cell_measurement_theta_min      3.9190
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.922
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            14127
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        56.513
_diffrn_reflns_theta_max         56.513
_diffrn_reflns_theta_min         3.783
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      159.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  36.00   0.50    1.00    --    0.82 -77.00 -60.00  154
  2  ω     -6.00  19.00   0.50    1.00    --    0.82-100.00 -78.00   50
  3  ω      4.00  29.00   0.50    1.00    --   -2.85-100.00 -78.00   50
  4  ω     39.00  89.00   0.50    1.00    --    0.82-179.00 -60.00  100
  5  ω     38.00 109.00   0.50    4.00    --   75.30-100.00 -78.00  142
  6  ω     17.00 116.00   0.50    4.00    --   75.30-125.00 -60.00  198
  7  ω     54.00  98.00   0.50    4.00    --   75.30-125.00  90.00   88
  8  ω     16.00  41.00   0.50    4.00    --   75.30-125.00  90.00   50
  9  ω     -4.00  76.00   0.50    1.00    --    0.82  57.00 120.00  160
 10  ω     97.00 122.00   0.50    4.00    --   75.30 100.00  26.00   50
 11  ω     88.00 155.00   0.50    4.00    --   75.30 125.00 -60.00  134
 12  ω     75.00 155.00   0.50    4.00    --   75.30 125.00 150.00  160
 13  ω    -28.00  61.00   0.50    1.00    --    0.82  57.00  90.00  178
 14  ω    -44.00 -19.00   0.50    1.00    --    0.82 100.00  26.00   50
 15  ω    -38.00   7.00   0.50    1.00    --   -2.85 100.00  26.00   90
 16  ω    -87.00 -62.00   0.50    4.00    --  -77.33 100.00  26.00   50
 17  ω    -81.00 -45.00   0.50    1.00    --   -2.85 179.00  30.00   72
 18  ω   -115.00   2.00   0.50    4.00    --  -77.33  77.00-150.00  234
 19  ω    -64.00 -38.00   0.50    4.00    --  -77.33 125.00-180.00   52
 20  ω   -153.00 -50.00   0.50    4.00    --  -77.33 -61.00  60.00  206
 21  ω   -125.00-100.00   0.50    4.00    --  -77.33-100.00 -78.00   50
 22  ω   -126.00 -45.00   0.50    4.00    --  -77.33 -61.00 -60.00  162
 23  ω   -138.00 -84.00   0.50    4.00    --  -77.33 -94.00 -30.00  108
 24  ω   -135.00 -81.00   0.50    4.00    --  -77.33-125.00-120.00  108
 25  ω   -138.00 -58.00   0.50    4.00    --  -77.33 -61.00 -30.00  160
 26  ω   -143.00 -52.00   0.50    4.00    --  -77.33 -61.00  90.00  182
 27  ω   -155.00 -81.00   0.50    4.00    --  -77.33-125.00  30.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0291307000
_diffrn_orient_matrix_UB_12      0.1056131000
_diffrn_orient_matrix_UB_13      0.0290832000
_diffrn_orient_matrix_UB_21      0.0587193000
_diffrn_orient_matrix_UB_22      0.0200886000
_diffrn_orient_matrix_UB_23      0.0302190000
_diffrn_orient_matrix_UB_31      0.0071284000
_diffrn_orient_matrix_UB_32      0.2673773000
_diffrn_orient_matrix_UB_33      -0.0137924000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2064
_reflns_number_total             2991
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     54.18
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         2991
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.036
_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)+(0.0827P)²+4.3883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1571
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2. Restrained distances
 H4-O4
 0.9 with sigma of 0.02
 H5-O5 = H1-O1
 0.9 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C22(H22A,H22B), C24(H24A,H24B), C23(H23A,H23B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C3(H3), C13(H13), C10(H10), C15(H15), C8(H8), C4(H4A),
 C12(H12), C19(H19), C18(H18)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.57169(11) 0.1707(4) 0.59935(7) 0.0519(7) Uani 1 1 d D . . . .
O2 O 0.50672(10) 0.5639(4) 0.56970(7) 0.0527(7) Uani 1 1 d . . . . .
O3 O 0.67213(11) 1.1086(4) 0.44234(7) 0.0546(7) Uani 1 1 d . . . . .
O4 O 0.71632(11) 1.1507(4) 0.38758(8) 0.0546(7) Uani 1 1 d D . . . .
O6 O 0.85101(12) 0.8922(5) 0.22839(7) 0.0610(7) Uani 1 1 d . . . . .
O7 O 0.51072(11) 0.8096(5) 0.36535(7) 0.0615(7) Uani 1 1 d . . . . .
O5 O 0.91852(11) 0.5046(5) 0.25815(8) 0.0611(8) Uani 1 1 d D . . . .
O8 O 0.56973(12) 0.9229(5) 0.31168(8) 0.0675(8) Uani 1 1 d . . . . .
C5 C 0.62162(14) 0.6191(6) 0.52135(10) 0.0407(9) Uani 1 1 d . . . . .
C7 C 0.63897(14) 0.7765(6) 0.49418(9) 0.0423(9) Uani 1 1 d . . . . .
H7 H 0.623443 0.936602 0.490592 0.051 Uiso 1 1 calc R U . . .
C2 C 0.58684(15) 0.3171(6) 0.57347(9) 0.0414(9) Uani 1 1 d . . . . .
C1 C 0.55436(14) 0.5297(6) 0.55781(10) 0.0415(8) Uani 1 1 d . . . . .
C14 C 0.81679(15) 0.8126(6) 0.32072(10) 0.0453(9) Uani 1 1 d . . . . .
C11 C 0.73391(14) 0.9157(6) 0.39434(10) 0.0425(9) Uani 1 1 d . . . . .
C6 C 0.57284(15) 0.6774(6) 0.53265(10) 0.0455(9) Uani 1 1 d . . . . .
H6 H 0.552189 0.820632 0.522851 0.055 Uiso 1 1 calc R U . . .
C9 C 0.68946(15) 0.8786(6) 0.44638(10) 0.0442(9) Uani 1 1 d . . . . .
C3 C 0.63470(15) 0.2573(6) 0.56286(10) 0.0448(9) Uani 1 1 d . . . . .
H3 H 0.655904 0.116585 0.573253 0.054 Uiso 1 1 calc R U . . .
C13 C 0.78145(15) 0.9203(7) 0.34284(10) 0.0468(9) Uani 1 1 d . . . . .
H13 H 0.767892 1.081852 0.336536 0.056 Uiso 1 1 calc R U . . .
C10 C 0.72121(14) 0.7822(6) 0.42307(10) 0.0462(9) Uani 1 1 d . . . . .
H10 H 0.734438 0.618493 0.427287 0.055 Uiso 1 1 calc R U . . .
C15 C 0.81622(16) 0.9119(7) 0.28526(10) 0.0485(9) Uani 1 1 d . . . . .
H15 H 0.793063 1.049311 0.275903 0.058 Uiso 1 1 calc R U . . .
C8 C 0.67435(15) 0.7179(6) 0.47395(10) 0.0454(9) Uani 1 1 d . . . . .
H8 H 0.690952 0.559873 0.477758 0.054 Uiso 1 1 calc R U . . .
C4 C 0.65197(15) 0.4040(6) 0.53678(10) 0.0447(9) Uani 1 1 d . . . . .
H4A H 0.684185 0.358569 0.529466 0.054 Uiso 1 1 calc R U . . .
C12 C 0.76681(15) 0.8080(7) 0.37129(10) 0.0458(9) Uani 1 1 d . . . . .
H12 H 0.779077 0.643902 0.376776 0.055 Uiso 1 1 calc R U . . .
C17 C 0.88400(16) 0.6052(7) 0.27784(10) 0.0471(9) Uani 1 1 d . . . . .
C16 C 0.84888(16) 0.8127(7) 0.26370(10) 0.0475(9) Uani 1 1 d . . . . .
C19 C 0.85177(16) 0.6071(7) 0.33411(11) 0.0540(10) Uani 1 1 d . . . . .
H19 H 0.852883 0.536372 0.357659 0.065 Uiso 1 1 calc R U . . .
C20 C 0.46810(15) 0.7568(7) 0.55097(11) 0.0537(10) Uani 1 1 d . . . . .
H20A H 0.457117 0.729220 0.523791 0.081 Uiso 1 1 calc R U . . .
H20B H 0.486594 0.916464 0.556614 0.081 Uiso 1 1 calc R U . . .
H20C H 0.434684 0.753949 0.559955 0.081 Uiso 1 1 calc R U . . .
C18 C 0.88490(16) 0.5078(7) 0.31252(11) 0.0553(10) Uani 1 1 d . . . . .
H18 H 0.908327 0.371277 0.321931 0.066 Uiso 1 1 calc R U . . .
C25 C 0.51192(17) 0.9902(8) 0.30544(12) 0.0624(11) Uani 1 1 d . . . . .
H25A H 0.487648 0.859402 0.290890 0.075 Uiso 1 1 calc R U . . .
H25B H 0.504200 1.142820 0.290441 0.075 Uiso 1 1 calc R U . . .
C21 C 0.81361(18) 1.0943(7) 0.21135(11) 0.0602(11) Uani 1 1 d . . . . .
H21A H 0.818532 1.133092 0.186722 0.090 Uiso 1 1 calc R U . . .
H21B H 0.822665 1.238947 0.227591 0.090 Uiso 1 1 calc R U . . .
H21C H 0.774638 1.046142 0.208339 0.090 Uiso 1 1 calc R U . . .
C22 C 0.56824(18) 0.7450(9) 0.37194(11) 0.0664(12) Uani 1 1 d . . . . .
H22A H 0.576012 0.592397 0.386944 0.080 Uiso 1 1 calc R U . . .
H22B H 0.592095 0.876454 0.386628 0.080 Uiso 1 1 calc R U . . .
C24 C 0.4979(2) 1.0289(8) 0.34193(13) 0.0766(13) Uani 1 1 d . . . . .
H24A H 0.519737 1.169109 0.355538 0.092 Uiso 1 1 calc R U . . .
H24B H 0.457570 1.068461 0.336685 0.092 Uiso 1 1 calc R U . . .
C23 C 0.5830(2) 0.7074(9) 0.33555(13) 0.0843(15) Uani 1 1 d . . . . .
H23A H 0.623571 0.671251 0.341145 0.101 Uiso 1 1 calc R U . . .
H23B H 0.562047 0.564809 0.322073 0.101 Uiso 1 1 calc R U . . .
H4 H 0.6982(15) 1.165(7) 0.4074(9) 0.070(13) Uiso 1 1 d D . . . .
H1 H 0.5389(11) 0.205(7) 0.6055(10) 0.056(11) Uiso 1 1 d D . . . .
H5 H 0.915(2) 0.562(9) 0.2335(8) 0.105(18) Uiso 1 1 d D . . . .


_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 C2 1.354(4) . ?
O1 H1 0.908(19) . ?
O2 C1 1.362(4) . ?
O2 C20 1.431(4) . ?
O3 C9 1.295(4) . ?
O4 C11 1.328(4) . ?
O4 H4 0.951(19) . ?
O6 C16 1.368(4) . ?
O6 C21 1.436(4) . ?
O7 C22 1.397(5) . ?
O7 C24 1.430(5) . ?
O5 C17 1.361(4) . ?
O5 H5 0.93(2) . ?
O8 C25 1.409(5) . ?
O8 C23 1.423(5) . ?
C5 C7 1.450(5) . ?
C5 C6 1.399(5) . ?
C5 C4 1.396(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.321(5) . ?
C2 C1 1.409(5) . ?
C2 C3 1.367(5) . ?
C1 C6 1.378(5) . ?
C14 C13 1.454(5) . ?
C14 C15 1.392(5) . ?
C14 C19 1.391(5) . ?
C11 C10 1.372(5) . ?
C11 C12 1.435(5) . ?
C6 H6 0.9300 . ?
C9 C10 1.399(5) . ?
C9 C8 1.446(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.330(5) . ?
C10 H10 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.373(5) . ?
C8 H8 0.9300 . ?
C4 H4A 0.9300 . ?
C12 H12 0.9300 . ?
C17 C16 1.406(5) . ?
C17 C18 1.360(5) . ?
C19 H19 0.9300 . ?
C19 C18 1.383(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C18 H18 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C24 1.477(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.482(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?

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
C2 O1 H1 119(2) . . ?
C1 O2 C20 116.8(3) . . ?
C11 O4 H4 97(2) . . ?
C16 O6 C21 116.8(3) . . ?
C22 O7 C24 110.1(3) . . ?
C17 O5 H5 119(3) . . ?
C25 O8 C23 110.4(3) . . ?
C6 C5 C7 120.5(3) . . ?
C4 C5 C7 121.9(3) . . ?
C4 C5 C6 117.6(3) . . ?
C5 C7 H7 116.4 . . ?
C8 C7 C5 127.3(3) . . ?
C8 C7 H7 116.4 . . ?
O1 C2 C1 121.0(3) . . ?
O1 C2 C3 119.0(3) . . ?
C3 C2 C1 120.1(3) . . ?
O2 C1 C2 114.3(3) . . ?
O2 C1 C6 127.1(3) . . ?
C6 C1 C2 118.6(3) . . ?
C15 C14 C13 120.7(3) . . ?
C19 C14 C13 121.3(3) . . ?
C19 C14 C15 118.0(3) . . ?
O4 C11 C10 120.2(3) . . ?
O4 C11 C12 118.4(3) . . ?
C10 C11 C12 121.4(3) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 C5 122.2(3) . . ?
C1 C6 H6 118.9 . . ?
O3 C9 C10 120.0(3) . . ?
O3 C9 C8 120.3(3) . . ?
C10 C9 C8 119.7(3) . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C14 C13 H13 117.1 . . ?
C12 C13 C14 125.8(3) . . ?
C12 C13 H13 117.1 . . ?
C11 C10 C9 123.6(3) . . ?
C11 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.9(3) . . ?
C16 C15 H15 119.1 . . ?
C7 C8 C9 125.5(3) . . ?
C7 C8 H8 117.2 . . ?
C9 C8 H8 117.2 . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4A 119.6 . . ?
C11 C12 H12 116.9 . . ?
C13 C12 C11 126.3(3) . . ?
C13 C12 H12 116.9 . . ?
O5 C17 C16 121.5(3) . . ?
C18 C17 O5 119.2(3) . . ?
C18 C17 C16 119.3(3) . . ?
O6 C16 C15 126.8(3) . . ?
O6 C16 C17 114.0(3) . . ?
C15 C16 C17 119.1(3) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C18 C19 121.5(4) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
O8 C25 H25A 109.3 . . ?
O8 C25 H25B 109.3 . . ?
O8 C25 C24 111.5(4) . . ?
H25A C25 H25B 108.0 . . ?
C24 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
O6 C21 H21A 109.5 . . ?
O6 C21 H21B 109.5 . . ?
O6 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O7 C22 H22A 109.3 . . ?
O7 C22 H22B 109.3 . . ?
O7 C22 C23 111.5(3) . . ?
H22A C22 H22B 108.0 . . ?
C23 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
O7 C24 C25 110.7(3) . . ?
O7 C24 H24A 109.5 . . ?
O7 C24 H24B 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
O8 C23 C22 111.4(4) . . ?
O8 C23 H23A 109.4 . . ?
O8 C23 H23B 109.4 . . ?
C22 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?

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 C1 O2 -2.7(4) . . . . ?
O1 C2 C1 C6 177.6(3) . . . . ?
O1 C2 C3 C4 -179.3(3) . . . . ?
O2 C1 C6 C5 -177.6(3) . . . . ?
O3 C9 C10 C11 -2.6(6) . . . . ?
O3 C9 C8 C7 6.5(6) . . . . ?
O4 C11 C10 C9 0.6(5) . . . . ?
O4 C11 C12 C13 -0.8(5) . . . . ?
O7 C22 C23 O8 56.2(5) . . . . ?
O5 C17 C16 O6 2.9(5) . . . . ?
O5 C17 C16 C15 -178.0(3) . . . . ?
O5 C17 C18 C19 178.3(4) . . . . ?
O8 C25 C24 O7 -57.0(5) . . . . ?
C5 C7 C8 C9 178.4(3) . . . . ?
C7 C5 C6 C1 178.7(3) . . . . ?
C7 C5 C4 C3 179.7(3) . . . . ?
C2 C1 C6 C5 1.9(5) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C14 C13 C12 C11 177.3(3) . . . . ?
C14 C15 C16 O6 178.9(3) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C14 C19 C18 C17 -0.5(6) . . . . ?
C6 C5 C7 C8 -162.3(4) . . . . ?
C6 C5 C4 C3 -1.2(5) . . . . ?
C3 C2 C1 O2 177.9(3) . . . . ?
C3 C2 C1 C6 -1.7(5) . . . . ?
C13 C14 C15 C16 -179.6(3) . . . . ?
C13 C14 C19 C18 179.9(4) . . . . ?
C10 C11 C12 C13 180.0(4) . . . . ?
C10 C9 C8 C7 -171.2(3) . . . . ?
C15 C14 C13 C12 161.4(4) . . . . ?
C15 C14 C19 C18 0.3(5) . . . . ?
C8 C9 C10 C11 175.2(3) . . . . ?
C4 C5 C7 C8 16.9(5) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C12 C11 C10 C9 179.8(3) . . . . ?
C16 C17 C18 C19 0.4(6) . . . . ?
C19 C14 C13 C12 -18.2(6) . . . . ?
C19 C14 C15 C16 0.0(5) . . . . ?
C20 O2 C1 C2 -171.9(3) . . . . ?
C20 O2 C1 C6 7.6(5) . . . . ?
C18 C17 C16 O6 -179.3(3) . . . . ?
C18 C17 C16 C15 -0.1(5) . . . . ?
C25 O8 C23 C22 -54.7(5) . . . . ?
C21 O6 C16 C15 -2.6(5) . . . . ?
C21 O6 C16 C17 176.5(3) . . . . ?
C22 O7 C24 C25 56.9(5) . . . . ?
C24 O7 C22 C23 -56.6(5) . . . . ?
C23 O8 C25 C24 55.6(5) . . . . ?

_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 1.659
_oxdiff_exptl_absorpt_empirical_full_min 0.731
####################################################################### 
# 
# 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_034236_wxx_160k_a
_database_code_depnum_ccdc_archive 'CCDC 2016128'
loop_
_audit_author_name
_audit_author_address
'Jun Xu'
;Tianjing University
China
;
_audit_update_record             
;
2020-07-14 deposited with the CCDC.	2020-11-04 downloaded from the CCDC.
;
_audit_creation_date             2020-07-10
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.05.07 svn.rd67b107b for OlexSys, GUI svn.r6105)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C2 H4 O), C21 H20 O6'
_chemical_formula_sum            'C27 H32 O9'
_chemical_formula_weight         500.52
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   21.7077(6)
_cell_length_b                   5.14640(10)
_cell_length_c                   22.8388(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.345(2)
_cell_angle_gamma                90
_cell_volume                     2544.14(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4864
_cell_measurement_temperature    160.00(10)
_cell_measurement_theta_max      72.9680
_cell_measurement_theta_min      2.7350
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16343
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.474
_diffrn_reflns_theta_min         2.708
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  77.00   0.50    1.00    --   45.62 -96.00  72.00  190
  2  ω     42.00 109.00   0.50   10.00    --  101.75 -96.00  72.00  134
  3  ω     73.00 126.00   0.50   10.00    --  101.75 -77.00 -60.00  106
  4  ω     60.00 118.00   0.50    1.00    --   45.62  38.00   0.00  116
  5  ω    149.00 174.00   0.50   10.00    --  101.75  45.00 120.00   50
  6  ω     97.00 124.00   0.50   10.00    --  101.75  45.00 120.00   54
  7  ω     29.00  55.00   0.50   10.00    --  101.75 -77.00 -60.00   52
  8  ω     95.00 122.00   0.50   10.00    --  101.75  96.00-178.00   54
  9  ω    -69.00  26.00   0.50    1.00    --  -45.62  96.00-178.00  190
 10  ω    -60.00 -28.00   0.50   10.00    -- -100.00 125.00-150.00   64
 11  ω    -96.00 -61.00   0.50   10.00    -- -100.00  96.00-178.00   70
 12  ω   -117.00 -76.00   0.50   10.00    -- -100.00 125.00-150.00   82
 13  ω   -113.00 -27.00   0.50   10.00    -- -100.00  45.00-180.00  172
 14  ω   -113.00 -74.00   0.50    1.00    --  -45.62-125.00-150.00   78
 15  ω   -167.00 -95.00   0.50   10.00    -- -100.00 -45.00   0.00  144
 16  ω   -172.00 -79.00   0.50   10.00    -- -100.00 -96.00  72.00  186
 17  ω   -118.00 -91.00   0.50    1.00    --  -45.62-125.00 150.00   54
 18  ω   -171.00-118.00   0.50   10.00    -- -100.00 -45.00 -30.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0131689000
_diffrn_orient_matrix_UB_12      -0.1668015000
_diffrn_orient_matrix_UB_13      -0.0555530000
_diffrn_orient_matrix_UB_21      0.0209708000
_diffrn_orient_matrix_UB_22      0.2257895000
_diffrn_orient_matrix_UB_23      -0.0380318000
_diffrn_orient_matrix_UB_31      0.0667603000
_diffrn_orient_matrix_UB_32      -0.1037561000
_diffrn_orient_matrix_UB_33      0.0064830000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3618
_reflns_number_total             4893
_reflns_odcompleteness_completeness 99.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4893
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0835P)²+0.3829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1496
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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) groups
2. Restrained distances
 O4-H4
 0.9 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C26(H26A,H26B), C23(H23A,H23B), C22(H22A,H22B), C24(H24A,
 H24B), C25(H25A,H25B)
3.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C10(H10), C12(H12), C13(H13), C6(H6), C19(H19), C18(H18), C4(H4A),
 C8(H8), C7(H7), C3(H3)
3.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C)
3.d Idealised tetrahedral OH refined as rotating group:
 O5(H5), O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O9 O 0.54280(7) 0.6721(3) 0.47793(6) 0.0443(3) Uani 1 1 d . . . . .
O5 O 0.87872(7) 0.4289(3) 0.08713(6) 0.0460(4) Uani 1 1 d . . . . .
H5 H 0.905491 0.326385 0.078487 0.069 Uiso 1 1 calc R U . . .
O6 O 0.94109(7) 0.0628(3) 0.15348(6) 0.0468(4) Uani 1 1 d . . . . .
O2 O 0.64608(7) 0.7288(3) 0.80738(6) 0.0482(4) Uani 1 1 d . . . . .
O1 O 0.57143(7) 1.1189(3) 0.76781(6) 0.0508(4) Uani 1 1 d . . . . .
H1 H 0.576739 1.055155 0.800711 0.076 Uiso 1 1 calc R U . . .
O7 O 0.95146(7) 0.5516(3) 0.62014(6) 0.0485(4) Uani 1 1 d . . . . .
O3 O 0.77010(8) 0.2541(3) 0.53279(6) 0.0509(4) Uani 1 1 d . . . . .
O4 O 0.81665(8) 0.1821(3) 0.43855(6) 0.0508(4) Uani 1 1 d D . . . .
O8 O 1.00883(8) 0.1579(4) 0.55774(8) 0.0587(4) Uani 1 1 d . . . . .
C16 C 0.89981(9) 0.2130(4) 0.18067(8) 0.0365(4) Uani 1 1 d . . . . .
C15 C 0.88691(9) 0.1919(4) 0.23889(8) 0.0376(4) Uani 1 1 d . . . . .
H15 H 0.906553 0.063950 0.262229 0.045 Uiso 1 1 calc R U . . .
C17 C 0.86866(9) 0.4007(4) 0.14504(8) 0.0373(4) Uani 1 1 d . . . . .
C5 C 0.67116(9) 0.7186(4) 0.64799(8) 0.0392(4) Uani 1 1 d . . . . .
C10 C 0.75885(9) 0.5547(4) 0.45568(8) 0.0411(4) Uani 1 1 d . . . . .
H10 H 0.742784 0.712580 0.441825 0.049 Uiso 1 1 calc R U . . .
C12 C 0.80213(9) 0.4759(4) 0.35950(8) 0.0392(4) Uani 1 1 d . . . . .
H12 H 0.785996 0.632150 0.344747 0.047 Uiso 1 1 calc R U . . .
C2 C 0.60560(9) 0.9876(4) 0.73035(8) 0.0397(4) Uani 1 1 d . . . . .
C14 C 0.84498(8) 0.3585(4) 0.26338(8) 0.0367(4) Uani 1 1 d . . . . .
C1 C 0.64408(9) 0.7801(4) 0.74835(8) 0.0379(4) Uani 1 1 d . . . . .
C13 C 0.83359(9) 0.3226(4) 0.32490(8) 0.0387(4) Uani 1 1 d . . . . .
H13 H 0.850419 0.173203 0.342534 0.046 Uiso 1 1 calc R U . . .
C11 C 0.79267(9) 0.4026(4) 0.41990(8) 0.0392(4) Uani 1 1 d . . . . .
C6 C 0.67568(9) 0.6459(4) 0.70768(8) 0.0397(4) Uani 1 1 d . . . . .
H6 H 0.700347 0.505327 0.719859 0.048 Uiso 1 1 calc R U . . .
C19 C 0.81546(9) 0.5478(4) 0.22765(8) 0.0404(4) Uani 1 1 d . . . . .
H19 H 0.787616 0.661435 0.243154 0.048 Uiso 1 1 calc R U . . .
C9 C 0.74849(9) 0.4724(4) 0.51314(8) 0.0407(4) Uani 1 1 d . . . . .
C18 C 0.82762(9) 0.5670(4) 0.16881(8) 0.0408(5) Uani 1 1 d . . . . .
H18 H 0.807753 0.693715 0.145283 0.049 Uiso 1 1 calc R U . . .
C4 C 0.63385(9) 0.9301(4) 0.63121(8) 0.0417(5) Uani 1 1 d . . . . .
H4A H 0.630605 0.983388 0.592191 0.050 Uiso 1 1 calc R U . . .
C8 C 0.71359(9) 0.6358(4) 0.55065(8) 0.0413(5) Uani 1 1 d . . . . .
H8 H 0.696287 0.788937 0.535305 0.050 Uiso 1 1 calc R U . . .
C7 C 0.70541(9) 0.5737(4) 0.60669(8) 0.0415(5) Uani 1 1 d . . . . .
H7 H 0.723818 0.420187 0.620590 0.050 Uiso 1 1 calc R U . . .
C3 C 0.60159(9) 1.0618(5) 0.67192(9) 0.0439(5) Uani 1 1 d . . . . .
H3 H 0.576848 1.202349 0.659866 0.053 Uiso 1 1 calc R U . . .
C21 C 0.97795(10) -0.1135(5) 0.18947(9) 0.0482(5) Uani 1 1 d . . . . .
H21A H 1.006320 -0.201418 0.165995 0.072 Uiso 1 1 calc R U . . .
H21B H 0.951688 -0.238606 0.206338 0.072 Uiso 1 1 calc R U . . .
H21C H 1.000620 -0.018822 0.220260 0.072 Uiso 1 1 calc R U . . .
C27 C 0.47803(10) 0.6973(5) 0.46311(9) 0.0466(5) Uani 1 1 d . . . . .
H27A H 0.466745 0.601163 0.427363 0.056 Uiso 1 1 calc R U . . .
H27B H 0.467846 0.878677 0.456033 0.056 Uiso 1 1 calc R U . . .
C20 C 0.68570(11) 0.5243(5) 0.82897(9) 0.0493(5) Uani 1 1 d . . . . .
H20A H 0.671219 0.362277 0.812260 0.074 Uiso 1 1 calc R U . . .
H20B H 0.685687 0.515936 0.870962 0.074 Uiso 1 1 calc R U . . .
H20C H 0.726920 0.556773 0.818256 0.074 Uiso 1 1 calc R U . . .
C26 C 0.55756(10) 0.4037(5) 0.48845(10) 0.0479(5) Uani 1 1 d . . . . .
H26A H 0.601481 0.385556 0.498987 0.057 Uiso 1 1 calc R U . . .
H26B H 0.547441 0.303782 0.453007 0.057 Uiso 1 1 calc R U . . .
C23 C 0.94321(11) 0.1811(5) 0.55589(11) 0.0564(6) Uani 1 1 d . . . . .
H23A H 0.927605 0.072239 0.586126 0.068 Uiso 1 1 calc R U . . .
H23B H 0.925262 0.120733 0.518137 0.068 Uiso 1 1 calc R U . . .
C22 C 0.92433(11) 0.4555(5) 0.56508(10) 0.0559(6) Uani 1 1 d . . . . .
H22A H 0.937407 0.562663 0.533356 0.067 Uiso 1 1 calc R U . . .
H22B H 0.879671 0.465545 0.564626 0.067 Uiso 1 1 calc R U . . .
C24 C 1.01678(11) 0.5282(5) 0.62201(10) 0.0555(6) Uani 1 1 d . . . . .
H24A H 1.034844 0.588213 0.659752 0.067 Uiso 1 1 calc R U . . .
H24B H 1.032540 0.636183 0.591704 0.067 Uiso 1 1 calc R U . . .
C25 C 1.03479(12) 0.2520(6) 0.61285(12) 0.0616(6) Uani 1 1 d . . . . .
H25A H 1.079457 0.238983 0.614245 0.074 Uiso 1 1 calc R U . . .
H25B H 1.020576 0.145557 0.644179 0.074 Uiso 1 1 calc R U . . .
H4 H 0.804(2) 0.171(9) 0.4763(11) 0.145(17) Uiso 1 1 d D . . . .


_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
O9 C27 1.427(3) . ?
O9 C26 1.434(3) . ?
O5 H5 0.8200 . ?
O5 C17 1.365(2) . ?
O6 C16 1.368(2) . ?
O6 C21 1.428(2) . ?
O2 C1 1.371(2) . ?
O2 C20 1.423(3) . ?
O1 H1 0.8200 . ?
O1 C2 1.355(2) . ?
O7 C22 1.436(3) . ?
O7 C24 1.420(3) . ?
O3 C9 1.286(3) . ?
O4 C11 1.306(3) . ?
O4 H4 0.926(19) . ?
O8 C23 1.427(3) . ?
O8 C25 1.424(3) . ?
C16 C15 1.384(3) . ?
C16 C17 1.403(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.398(3) . ?
C17 C18 1.376(3) . ?
C5 C6 1.410(3) . ?
C5 C4 1.393(3) . ?
C5 C7 1.451(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(3) . ?
C10 C9 1.413(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.340(3) . ?
C12 C11 1.459(3) . ?
C2 C1 1.398(3) . ?
C2 C3 1.384(3) . ?
C14 C13 1.457(3) . ?
C14 C19 1.395(3) . ?
C1 C6 1.381(3) . ?
C13 H13 0.9300 . ?
C6 H6 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.392(3) . ?
C9 C8 1.454(3) . ?
C18 H18 0.9300 . ?
C4 H4A 0.9300 . ?
C4 C3 1.383(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.344(3) . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C26 1.490(3) 3_666 ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C22 1.490(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.493(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?

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
C27 O9 C26 109.31(16) . . ?
C17 O5 H5 109.5 . . ?
C16 O6 C21 117.11(15) . . ?
C1 O2 C20 117.15(16) . . ?
C2 O1 H1 109.5 . . ?
C24 O7 C22 109.85(17) . . ?
C11 O4 H4 103(3) . . ?
C25 O8 C23 108.96(18) . . ?
O6 C16 C15 125.37(17) . . ?
O6 C16 C17 115.44(16) . . ?
C15 C16 C17 119.19(17) . . ?
C16 C15 H15 119.3 . . ?
C16 C15 C14 121.43(18) . . ?
C14 C15 H15 119.3 . . ?
O5 C17 C16 121.99(17) . . ?
O5 C17 C18 118.18(17) . . ?
C18 C17 C16 119.82(17) . . ?
C6 C5 C7 119.38(19) . . ?
C4 C5 C6 118.01(18) . . ?
C4 C5 C7 122.60(17) . . ?
C11 C10 H10 119.7 . . ?
C11 C10 C9 120.5(2) . . ?
C9 C10 H10 119.7 . . ?
C13 C12 H12 119.3 . . ?
C13 C12 C11 121.3(2) . . ?
C11 C12 H12 119.3 . . ?
O1 C2 C1 122.61(17) . . ?
O1 C2 C3 118.27(18) . . ?
C3 C2 C1 119.12(19) . . ?
C15 C14 C13 118.13(18) . . ?
C19 C14 C15 118.59(17) . . ?
C19 C14 C13 123.28(18) . . ?
O2 C1 C2 114.19(17) . . ?
O2 C1 C6 125.79(18) . . ?
C6 C1 C2 120.02(17) . . ?
C12 C13 C14 128.7(2) . . ?
C12 C13 H13 115.6 . . ?
C14 C13 H13 115.6 . . ?
O4 C11 C10 121.03(18) . . ?
O4 C11 C12 116.86(18) . . ?
C10 C11 C12 122.09(19) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 C5 121.07(19) . . ?
C1 C6 H6 119.5 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.11(18) . . ?
C18 C19 H19 119.9 . . ?
O3 C9 C10 120.44(19) . . ?
O3 C9 C8 119.52(18) . . ?
C10 C9 C8 120.04(19) . . ?
C17 C18 C19 120.82(18) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 C5 120.77(18) . . ?
C3 C4 H4A 119.6 . . ?
C9 C8 H8 118.8 . . ?
C7 C8 C9 122.4(2) . . ?
C7 C8 H8 118.8 . . ?
C5 C7 H7 116.3 . . ?
C8 C7 C5 127.4(2) . . ?
C8 C7 H7 116.3 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
O6 C21 H21A 109.5 . . ?
O6 C21 H21B 109.5 . . ?
O6 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O9 C27 H27A 109.6 . . ?
O9 C27 H27B 109.6 . . ?
O9 C27 C26 110.44(16) . 3_666 ?
H27A C27 H27B 108.1 . . ?
C26 C27 H27A 109.6 3_666 . ?
C26 C27 H27B 109.6 3_666 . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O9 C26 C27 109.79(18) . 3_666 ?
O9 C26 H26A 109.7 . . ?
O9 C26 H26B 109.7 . . ?
C27 C26 H26A 109.7 3_666 . ?
C27 C26 H26B 109.7 3_666 . ?
H26A C26 H26B 108.2 . . ?
O8 C23 H23A 109.4 . . ?
O8 C23 H23B 109.4 . . ?
O8 C23 C22 111.1(2) . . ?
H23A C23 H23B 108.0 . . ?
C22 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
O7 C22 C23 110.6(2) . . ?
O7 C22 H22A 109.5 . . ?
O7 C22 H22B 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
O7 C24 H24A 109.6 . . ?
O7 C24 H24B 109.6 . . ?
O7 C24 C25 110.4(2) . . ?
H24A C24 H24B 108.1 . . ?
C25 C24 H24A 109.6 . . ?
C25 C24 H24B 109.6 . . ?
O8 C25 C24 110.9(2) . . ?
O8 C25 H25A 109.5 . . ?
O8 C25 H25B 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 108.0 . . ?

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
O5 C17 C18 C19 -179.98(19) . . . . ?
O6 C16 C15 C14 178.42(19) . . . . ?
O6 C16 C17 O5 0.5(3) . . . . ?
O6 C16 C17 C18 -177.96(18) . . . . ?
O2 C1 C6 C5 -178.78(19) . . . . ?
O1 C2 C1 O2 -2.6(3) . . . . ?
O1 C2 C1 C6 177.1(2) . . . . ?
O1 C2 C3 C4 -177.97(19) . . . . ?
O7 C24 C25 O8 59.1(3) . . . . ?
O3 C9 C8 C7 3.4(3) . . . . ?
O8 C23 C22 O7 -57.8(3) . . . . ?
C16 C15 C14 C13 179.61(18) . . . . ?
C16 C15 C14 C19 0.6(3) . . . . ?
C16 C17 C18 C19 -1.4(3) . . . . ?
C15 C16 C17 O5 -179.09(19) . . . . ?
C15 C16 C17 C18 2.4(3) . . . . ?
C15 C14 C13 C12 170.6(2) . . . . ?
C15 C14 C19 C18 0.4(3) . . . . ?
C17 C16 C15 C14 -2.0(3) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C10 C9 C8 C7 -176.14(19) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C14 C19 C18 C17 0.0(3) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C13 C12 C11 O4 0.5(3) . . . . ?
C13 C12 C11 C10 -178.12(19) . . . . ?
C13 C14 C19 C18 -178.53(19) . . . . ?
C11 C10 C9 O3 -0.4(3) . . . . ?
C11 C10 C9 C8 179.13(18) . . . . ?
C11 C12 C13 C14 176.91(18) . . . . ?
C6 C5 C4 C3 -0.9(3) . . . . ?
C6 C5 C7 C8 -169.9(2) . . . . ?
C19 C14 C13 C12 -10.4(3) . . . . ?
C9 C10 C11 O4 -1.1(3) . . . . ?
C9 C10 C11 C12 177.37(18) . . . . ?
C9 C8 C7 C5 -179.25(19) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C7 C8 9.6(3) . . . . ?
C7 C5 C6 C1 179.60(19) . . . . ?
C7 C5 C4 C3 179.5(2) . . . . ?
C3 C2 C1 O2 177.96(19) . . . . ?
C3 C2 C1 C6 -2.4(3) . . . . ?
C21 O6 C16 C15 -6.2(3) . . . . ?
C21 O6 C16 C17 174.21(18) . . . . ?
C27 O9 C26 C27 -58.7(2) . . . 3_666 ?
C20 O2 C1 C2 -178.34(19) . . . . ?
C20 O2 C1 C6 2.1(3) . . . . ?
C26 O9 C27 C26 59.1(3) . . . 3_666 ?
C23 O8 C25 C24 -58.4(3) . . . . ?
C22 O7 C24 C25 -57.4(3) . . . . ?
C24 O7 C22 C23 57.0(3) . . . . ?
C25 O8 C23 C22 57.9(3) . . . . ?

_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 1.608
_oxdiff_exptl_absorpt_empirical_full_min 0.674
