# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_zhangwenjun_sh31-19_collect
_database_code_depnum_ccdc_archive 'CCDC 2072125'
loop_
_audit_author_name
_audit_author_address
'Lu Wang'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;
_audit_creation_date             2019-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11.95 H13.91 O4'
_chemical_formula_sum            'C12 H14 O4'
_chemical_formula_weight         222.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C44 H52 O20 '
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.6505(4)
_cell_length_b                   4.35190(10)
_cell_length_c                   17.2668(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.015(4)
_cell_angle_gamma                90
_cell_volume                     1065.72(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2179
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      73.6490
_cell_measurement_theta_min      6.4150
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.846
_exptl_absorpt_coefficient_mu    0.865
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4622
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.018
_diffrn_reflns_theta_min         5.175
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  31.00   0.50    1.00    --    0.00 -82.00 -30.00   90
  2  ω    -29.00  31.00   0.50    1.00    --    0.00 -82.00-150.00  120
  3  ω     -1.00  28.00   0.50    1.00    --    0.00 -82.00 120.00   58
  4  ω    -30.00  -3.00   0.50    1.00    --    0.00 -82.00 120.00   54
  5  ω    160.00 185.00   0.50    4.00    --   95.20  15.00 120.00   50
  6  ω     77.00 109.00   0.50    4.00    --   95.20 -45.00 -90.00   64
  7  ω     97.00 123.00   0.50    4.00    --   95.20  15.00 120.00   52
  8  ω      9.00 100.00   0.50    4.00    --   95.20 -45.00  30.00  182
  9  ω     79.00 181.00   0.50    4.00    --   95.20  61.00 150.00  204
 10  ω    133.00 183.00   0.50    4.00    --   95.20  82.00  30.00  100
 11  ω      7.00  73.00   0.50    4.00    --   95.20 -45.00 -90.00  132
 12  ω     17.00 106.00   0.50    4.00    --   95.20 -30.00  30.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0974018000
_diffrn_orient_matrix_UB_12      -0.0728837000
_diffrn_orient_matrix_UB_13      -0.0722647000
_diffrn_orient_matrix_UB_21      0.0135230000
_diffrn_orient_matrix_UB_22      0.2590769000
_diffrn_orient_matrix_UB_23      -0.0545677000
_diffrn_orient_matrix_UB_31      0.0461568000
_diffrn_orient_matrix_UB_32      -0.2300031000
_diffrn_orient_matrix_UB_33      -0.0385916000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                1783
_reflns_number_total             2097
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2097
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.077
_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)+(0.0682P)²+0.5610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1367
_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. Others
 Sof(H16a)=Sof(H16b)=Sof(H16c)=Sof(H2a)=Sof(H2b)=FVAR(1)
 Sof(C1)=Sof(H1)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C2(H2a,H2b)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6)
3.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c)
3.e Idealised tetrahedral OH refined as rotating group:
 O12(H12), O11(H11)
;
_atom_sites_solution_hydrogens   geom
_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
O10 O 0.81525(8) 0.3721(3) 0.70392(7) 0.0229(3) Uani 1 1 d . . . . .
O12 O 0.66583(8) 0.3455(3) 0.88909(7) 0.0245(3) Uani 1 1 d . . . . .
H12 H 0.615065 0.383472 0.890252 0.037 Uiso 1 1 calc GR . . . .
O11 O 0.52427(8) 0.9222(3) 0.63305(7) 0.0263(3) Uani 1 1 d . . . . .
H11 H 0.532203 0.961681 0.590106 0.039 Uiso 1 1 calc GR . . . .
O13 O 0.60884(8) 0.9178(3) 0.53192(8) 0.0336(4) Uani 1 1 d . . . . .
C7 C 0.66449(11) 0.4464(4) 0.81418(10) 0.0197(4) Uani 1 1 d . . . . .
C9 C 0.74069(10) 0.4603(4) 0.72088(10) 0.0195(4) Uani 1 1 d . . . . .
C5 C 0.59517(11) 0.7402(4) 0.68551(10) 0.0209(4) Uani 1 1 d . . . . .
C8 C 0.73958(10) 0.3494(4) 0.79547(10) 0.0192(4) Uani 1 1 d . . . . .
C6 C 0.59367(11) 0.6408(4) 0.76074(10) 0.0212(4) Uani 1 1 d . . . . .
H6 H 0.545741 0.703327 0.775575 0.025 Uiso 1 1 calc R . . . .
C4 C 0.66892(10) 0.6519(4) 0.66321(10) 0.0204(4) Uani 1 1 d . . . . .
C14 C 0.81775(11) 0.1519(4) 0.85711(10) 0.0217(4) Uani 1 1 d . . . . .
H14A H 0.842638 0.023848 0.825465 0.026 Uiso 1 1 calc R . . . .
H14B H 0.792526 0.017729 0.887235 0.026 Uiso 1 1 calc R . . . .
C3 C 0.67079(11) 0.7516(4) 0.58414(10) 0.0252(4) Uani 1 1 d . . . . .
C15 C 0.89725(12) 0.3438(4) 0.92169(11) 0.0284(4) Uani 1 1 d . . . . .
H15A H 0.924708 0.468661 0.892311 0.043 Uiso 1 1 calc GR . . . .
H15B H 0.944526 0.210383 0.961067 0.043 Uiso 1 1 calc GR . . . .
H15C H 0.872656 0.473571 0.952446 0.043 Uiso 1 1 calc GR . . . .
C16 C 0.91974(13) 0.4405(5) 0.63842(13) 0.0344(5) Uani 1 1 d . . . . .
H16A H 0.970969 0.406486 0.693372 0.052 Uiso 0.99(2) 1 calc GR . P A 1
H16B H 0.939584 0.578732 0.605885 0.052 Uiso 0.99(2) 1 calc GR . P A 1
H16C H 0.901024 0.248383 0.608645 0.052 Uiso 0.99(2) 1 calc GR . P A 1
C2 C 0.75239(13) 0.6364(5) 0.56769(12) 0.0324(5) Uani 1 1 d . . . . .
H2A H 0.734487 0.447437 0.534942 0.039 Uiso 0.99(2) 1 calc R . P A 1
H2B H 0.767921 0.787141 0.534267 0.039 Uiso 0.99(2) 1 calc R . P A 1
C1 C 0.83717(13) 0.5790(5) 0.65003(12) 0.0277(6) Uani 0.950(8) 1 d . . P B 1
H1 H 0.857373 0.775265 0.680103 0.033 Uiso 0.950(8) 1 calc R . P B 1


_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
O10 C9 1.3725(19) . ?
O10 C1 1.437(2) . ?
O12 H12 0.8200 . ?
O12 C7 1.3575(18) . ?
O11 H11 0.8200 . ?
O11 C5 1.3525(19) . ?
O13 C3 1.240(2) . ?
C7 C8 1.409(2) . ?
C7 C6 1.390(2) . ?
C9 C8 1.382(2) . ?
C9 C4 1.415(2) . ?
C5 C6 1.379(2) . ?
C5 C4 1.416(2) . ?
C8 C14 1.506(2) . ?
C6 H6 0.9300 . ?
C4 C3 1.444(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.522(2) . ?
C3 C2 1.506(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C1 1.514(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.500(3) . ?
C1 H1 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 O10 C1 114.86(13) . . ?
C7 O12 H12 109.5 . . ?
C5 O11 H11 109.5 . . ?
O12 C7 C8 116.31(14) . . ?
O12 C7 C6 121.09(14) . . ?
C6 C7 C8 122.58(14) . . ?
O10 C9 C8 116.61(14) . . ?
O10 C9 C4 120.53(14) . . ?
C8 C9 C4 122.85(14) . . ?
O11 C5 C6 118.61(14) . . ?
O11 C5 C4 120.60(14) . . ?
C6 C5 C4 120.79(15) . . ?
C7 C8 C14 121.07(14) . . ?
C9 C8 C7 116.71(14) . . ?
C9 C8 C14 122.10(14) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 C7 119.35(14) . . ?
C5 C6 H6 120.3 . . ?
C9 C4 C5 117.66(14) . . ?
C9 C4 C3 120.98(14) . . ?
C5 C4 C3 121.35(14) . . ?
C8 C14 H14A 109.2 . . ?
C8 C14 H14B 109.2 . . ?
C8 C14 C15 111.89(14) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
O13 C3 C4 122.72(15) . . ?
O13 C3 C2 121.44(15) . . ?
C4 C3 C2 115.84(14) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C16 H16A 109.5 . . ?
C1 C16 H16B 109.5 . . ?
C1 C16 H16C 109.5 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C1 C2 C3 110.95(14) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
O10 C1 C16 106.69(15) . . ?
O10 C1 C2 111.14(15) . . ?
O10 C1 H1 108.4 . . ?
C16 C1 H1 108.4 . . ?
C2 C1 C16 113.79(15) . . ?
C2 C1 H1 108.4 . . ?

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
O10 C9 C8 C7 178.32(14) . . . . ?
O10 C9 C8 C14 2.3(2) . . . . ?
O10 C9 C4 C5 -178.56(14) . . . . ?
O10 C9 C4 C3 1.9(2) . . . . ?
O12 C7 C8 C9 -177.65(14) . . . . ?
O12 C7 C8 C14 -1.6(2) . . . . ?
O12 C7 C6 C5 179.51(15) . . . . ?
O11 C5 C6 C7 178.14(15) . . . . ?
O11 C5 C4 C9 -179.79(15) . . . . ?
O11 C5 C4 C3 -0.2(3) . . . . ?
O13 C3 C2 C1 152.48(18) . . . . ?
C7 C8 C14 C15 -88.41(18) . . . . ?
C9 O10 C1 C16 -179.43(14) . . . . ?
C9 O10 C1 C2 -54.9(2) . . . . ?
C9 C8 C14 C15 87.41(19) . . . . ?
C9 C4 C3 O13 179.54(16) . . . . ?
C9 C4 C3 C2 0.6(2) . . . . ?
C5 C4 C3 O13 0.0(3) . . . . ?
C5 C4 C3 C2 -178.98(16) . . . . ?
C8 C7 C6 C5 1.2(3) . . . . ?
C8 C9 C4 C5 2.3(2) . . . . ?
C8 C9 C4 C3 -177.25(15) . . . . ?
C6 C7 C8 C9 0.8(2) . . . . ?
C6 C7 C8 C14 176.79(15) . . . . ?
C6 C5 C4 C9 -0.3(2) . . . . ?
C6 C5 C4 C3 179.30(16) . . . . ?
C4 C9 C8 C7 -2.5(2) . . . . ?
C4 C9 C8 C14 -178.51(15) . . . . ?
C4 C5 C6 C7 -1.4(3) . . . . ?
C4 C3 C2 C1 -28.5(2) . . . . ?
C3 C2 C1 O10 55.3(2) . . . . ?
C3 C2 C1 C16 175.73(17) . . . . ?
C1 O10 C9 C8 -154.87(15) . . . . ?
C1 O10 C9 C4 25.9(2) . . . . ?

_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 1.338
_oxdiff_exptl_absorpt_empirical_full_min 0.788
####################################################################### 
# 
# 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_zhangwenjun_sh31-18_collect
_database_code_depnum_ccdc_archive 'CCDC 2072148'
loop_
_audit_author_name
_audit_author_address
'Lu Wang'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;
_audit_creation_date             2019-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13.98 O4'
_chemical_formula_sum            'C11.92 H13.91 O4'
_chemical_formula_weight         221.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C48 H56 O16 '
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.1015(3)
_cell_length_b                   21.7906(18)
_cell_length_c                   10.1611(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.619(5)
_cell_angle_gamma                90
_cell_volume                     1102.27(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2200
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      72.9440
_cell_measurement_theta_min      4.8980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             470
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5466
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.999
_diffrn_reflns_theta_min         4.900
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  31.00   0.50    1.00    --    0.00 -82.00  30.00  118
  2  ω    -22.00   3.00   0.50    1.00    --    0.00 -77.00-180.00   50
  3  ω    -33.00  26.00   0.50    1.00    --    0.00 -82.00 -60.00  118
  4  ω    -43.00   6.00   0.50    1.00    --    0.00 -77.00-150.00   98
  5  ω     62.00 117.00   0.50    3.00    --   95.20 -61.00 120.00  110
  6  ω      8.00  50.00   0.50    3.00    --   95.20 -77.00 120.00   84
  7  ω     16.00  66.00   0.50    3.00    --   95.20 -30.00 120.00  100
  8  ω     79.00 185.00   0.50    3.00    --   95.20  45.00  30.00  212
  9  ω     62.00 102.00   0.50    3.00    --   95.20 -77.00 120.00   80
 10  ω     11.00  95.00   0.50    3.00    --   95.20 -45.00-180.00  168
 11  ω     14.00  60.00   0.50    3.00    --   95.20 -61.00 120.00   92
 12  ω     68.00 176.00   0.50    3.00    --   95.20   0.00 -30.00  216
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0669475000
_diffrn_orient_matrix_UB_12      0.0665849000
_diffrn_orient_matrix_UB_13      0.0319475000
_diffrn_orient_matrix_UB_21      0.1777567000
_diffrn_orient_matrix_UB_22      -0.0065156000
_diffrn_orient_matrix_UB_23      0.1428201000
_diffrn_orient_matrix_UB_31      0.2441605000
_diffrn_orient_matrix_UB_32      0.0229805000
_diffrn_orient_matrix_UB_33      -0.0521136000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                1760
_reflns_number_total             2144
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0575
_refine_ls_restrained_S_all      1.101
_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)+(0.0982P)²+0.3691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1707
_refine_ls_wR_factor_ref         0.1771
_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. Others
 Sof(H8a)=Sof(H8b)=Sof(H16a)=Sof(H16b)=Sof(H16c)=FVAR(1)
 Sof(C9A)=Sof(H9A)=1-FVAR(2)
 Sof(C9)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C9(H9), C9A(H9A)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C8(H8a,H8b)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2)
3.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c)
3.e Idealised tetrahedral OH refined as rotating group:
 O11(H11), O12(H12)
;
_atom_sites_solution_hydrogens   geom
_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
O10 O 0.5693(3) 0.64721(6) 0.32153(13) 0.0302(4) Uani 1 1 d . . . . .
O11 O 0.8430(3) 0.84639(7) 0.22072(14) 0.0309(4) Uani 1 1 d . . . . .
H11 H 0.936290 0.825703 0.181390 0.046 Uiso 1 1 calc GR . . . .
O13 O 0.1151(3) 0.71825(7) 0.57131(13) 0.0310(4) Uani 1 1 d . . . . .
O12 O 0.2572(3) 0.82730(7) 0.51463(13) 0.0305(4) Uani 1 1 d . . . . .
H12 H 0.173670 0.801073 0.546363 0.046 Uiso 1 1 calc GR . . . .
C1 C 0.5579(4) 0.70886(9) 0.33747(18) 0.0261(4) Uani 1 1 d . . . . .
C6 C 0.3998(4) 0.73551(9) 0.42168(17) 0.0263(5) Uani 1 1 d . . . . .
C4 C 0.5508(4) 0.83825(10) 0.36759(18) 0.0278(5) Uani 1 1 d . . . . .
C3 C 0.7039(4) 0.80894(10) 0.28670(17) 0.0264(5) Uani 1 1 d . . . . .
C5 C 0.4031(4) 0.80023(10) 0.43494(17) 0.0267(5) Uani 1 1 d . . . . .
C2 C 0.7091(4) 0.74539(10) 0.27113(18) 0.0263(4) Uani 1 1 d . . . . .
H2 H 0.813278 0.727773 0.216642 0.032 Uiso 1 1 calc R . . . .
C7 C 0.2516(4) 0.69697(10) 0.49304(17) 0.0282(5) Uani 1 1 d . . . . .
C14 C 0.5445(4) 0.90646(9) 0.38332(19) 0.0310(5) Uani 1 1 d . . . . .
H14A H 0.365506 0.918829 0.390506 0.037 Uiso 1 1 calc R . . . .
H14B H 0.582355 0.925674 0.303383 0.037 Uiso 1 1 calc R . . . .
C8 C 0.2659(5) 0.62927(11) 0.4713(2) 0.0347(5) Uani 1 1 d . . . . .
H8A H 0.095826 0.610682 0.476869 0.042 Uiso 0.98(2) 1 calc R . P A 1
H8B H 0.404386 0.611716 0.542115 0.042 Uiso 0.98(2) 1 calc R . P A 1
C9 C 0.3271(5) 0.61467(11) 0.3358(2) 0.0324(7) Uani 0.924(7) 1 d . . P B 1
H9 H 0.176226 0.628124 0.264458 0.039 Uiso 1 1 calc R . . . .
C15 C 0.7474(4) 0.92933(11) 0.5073(2) 0.0361(5) Uani 1 1 d . . . . .
H15A H 0.925662 0.918494 0.499285 0.054 Uiso 1 1 calc GR . . . .
H15B H 0.710123 0.910724 0.586881 0.054 Uiso 1 1 calc GR . . . .
H15C H 0.733887 0.973125 0.513597 0.054 Uiso 1 1 calc GR . . . .
C16 C 0.3796(6) 0.54780(11) 0.3163(3) 0.0485(7) Uani 1 1 d . . . . .
H16A H 0.413629 0.541624 0.227967 0.073 Uiso 0.98(2) 1 calc GR . P A 1
H16B H 0.225510 0.524211 0.325291 0.073 Uiso 0.98(2) 1 calc GR . P A 1
H16C H 0.533073 0.534828 0.383074 0.073 Uiso 0.98(2) 1 calc GR . P A 1
C9A C 0.495(5) 0.6075(11) 0.411(3) 0.025(8) Uani 0.076(7) 1 d . . P B 2
H9A H 0.650059 0.595889 0.482109 0.030 Uiso 0.076(7) 1 calc R . P B 2


_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
O10 C1 1.356(2) . ?
O10 C9 1.459(3) . ?
O10 C9A 1.37(2) . ?
O11 H11 0.8200 . ?
O11 C3 1.352(2) . ?
O13 C7 1.255(2) . ?
O12 H12 0.8200 . ?
O12 C5 1.349(2) . ?
C1 C6 1.422(3) . ?
C1 C2 1.382(3) . ?
C6 C5 1.416(3) . ?
C6 C7 1.429(3) . ?
C4 C3 1.405(3) . ?
C4 C5 1.396(3) . ?
C4 C14 1.496(3) . ?
C3 C2 1.395(3) . ?
C2 H2 0.9300 . ?
C7 C8 1.496(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.529(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.511(3) . ?
C8 C9A 1.51(3) . ?
C9 H9 0.9800 . ?
C9 C16 1.503(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C9A 1.65(3) . ?
C9A H9A 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
C1 O10 C9 114.22(16) . . ?
C1 O10 C9A 121.5(11) . . ?
C3 O11 H11 109.5 . . ?
C5 O12 H12 109.5 . . ?
O10 C1 C6 121.42(18) . . ?
O10 C1 C2 117.99(17) . . ?
C2 C1 C6 120.57(19) . . ?
C1 C6 C7 119.87(19) . . ?
C5 C6 C1 117.87(18) . . ?
C5 C6 C7 122.23(18) . . ?
C3 C4 C14 122.80(18) . . ?
C5 C4 C3 116.46(19) . . ?
C5 C4 C14 120.73(18) . . ?
O11 C3 C4 115.78(18) . . ?
O11 C3 C2 121.20(17) . . ?
C2 C3 C4 122.99(18) . . ?
O12 C5 C6 119.73(18) . . ?
O12 C5 C4 117.53(18) . . ?
C4 C5 C6 122.74(18) . . ?
C1 C2 C3 119.35(18) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
O13 C7 C6 122.2(2) . . ?
O13 C7 C8 120.62(18) . . ?
C6 C7 C8 117.17(18) . . ?
C4 C14 H14A 109.1 . . ?
C4 C14 H14B 109.1 . . ?
C4 C14 C15 112.67(17) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C7 C8 C9 111.62(18) . . ?
C7 C8 C9A 115.9(9) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
O10 C9 C8 109.67(17) . . ?
O10 C9 H9 109.0 . . ?
O10 C9 C16 106.19(19) . . ?
C8 C9 H9 109.0 . . ?
C16 C9 C8 113.77(19) . . ?
C16 C9 H9 109.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O10 C9A C8 114.9(16) . . ?
O10 C9A C16 103.0(16) . . ?
O10 C9A H9A 110.8 . . ?
C8 C9A C16 106.0(15) . . ?
C8 C9A H9A 110.8 . . ?
C16 C9A H9A 110.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O10 C1 C6 C5 178.78(16) . . . . ?
O10 C1 C6 C7 0.9(3) . . . . ?
O10 C1 C2 C3 -179.31(15) . . . . ?
O11 C3 C2 C1 -178.18(16) . . . . ?
O13 C7 C8 C9 154.42(18) . . . . ?
O13 C7 C8 C9A -162.1(11) . . . . ?
C1 O10 C9 C8 -56.1(2) . . . . ?
C1 O10 C9 C16 -179.48(17) . . . . ?
C1 O10 C9A C8 34(2) . . . . ?
C1 O10 C9A C16 149.3(7) . . . . ?
C1 C6 C5 O12 -179.55(15) . . . . ?
C1 C6 C5 C4 1.0(3) . . . . ?
C1 C6 C7 O13 178.05(16) . . . . ?
C1 C6 C7 C8 -1.7(2) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C6 C7 C8 C9 -25.8(2) . . . . ?
C6 C7 C8 C9A 17.6(11) . . . . ?
C4 C3 C2 C1 0.0(3) . . . . ?
C3 C4 C5 O12 179.16(16) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C3 C4 C14 C15 -94.3(2) . . . . ?
C5 C6 C7 O13 0.2(3) . . . . ?
C5 C6 C7 C8 -179.55(17) . . . . ?
C5 C4 C3 O11 179.16(16) . . . . ?
C5 C4 C3 C2 0.9(3) . . . . ?
C5 C4 C14 C15 85.2(2) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 -177.94(16) . . . . ?
C7 C6 C5 O12 -1.7(3) . . . . ?
C7 C6 C5 C4 178.85(16) . . . . ?
C7 C8 C9 O10 53.6(2) . . . . ?
C7 C8 C9 C16 172.4(2) . . . . ?
C7 C8 C9A O10 -33(2) . . . . ?
C7 C8 C9A C16 -146.5(7) . . . . ?
C14 C4 C3 O11 -1.3(3) . . . . ?
C14 C4 C3 C2 -179.62(17) . . . . ?
C14 C4 C5 O12 -0.4(3) . . . . ?
C14 C4 C5 C6 179.09(16) . . . . ?
C9 O10 C1 C6 29.2(2) . . . . ?
C9 O10 C1 C2 -151.97(17) . . . . ?
C9A O10 C1 C6 -18.5(13) . . . . ?
C9A O10 C1 C2 160.3(13) . . . . ?

_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 1.756
_oxdiff_exptl_absorpt_empirical_full_min 0.572
####################################################################### 
# 
# 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 
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data_zhangwenjun_sh31-11_collect2_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2072145'
loop_
_audit_author_name
_audit_author_address
'Lu Wang'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;
_audit_creation_date             2019-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C13 H16 O5), 6(H2 O)'
_chemical_formula_sum            'C52 H76 O26'
_chemical_formula_weight         1117.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C50 H72 N2 O26 '
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3819(6)
_cell_length_b                   12.0675(7)
_cell_length_c                   12.3012(6)
_cell_angle_alpha                70.999(5)
_cell_angle_beta                 84.623(5)
_cell_angle_gamma                83.524(5)
_cell_volume                     1445.20(14)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    15597
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      73.6900
_cell_measurement_theta_min      3.7560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.874
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10544
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.499
_diffrn_reflns_theta_min         4.495
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  27.00   0.50    1.50    --    0.00 -82.00 -30.00  104
  2  ω     16.00  44.00   0.50    1.50    --   36.00  68.00  51.05   56
  3  ω     82.00 120.00   0.50    1.50    --   36.00  68.00  51.05   76
  4  ω    -49.00  58.00   0.50    1.50    --   40.00 -43.00 140.16  214
  5  ω     14.00  70.00   0.50    1.50    --   40.00  72.00 -77.83  112
  6  ω     58.00  98.00   0.50    1.50    --   44.00  72.00 129.06   80
  7  ω     17.00  49.00   0.50    1.50    --   44.00  72.00 129.06   64
  8  ω     98.00 127.00   0.50    3.50    --   56.00  75.00 140.09   58
  9  ω     33.00  79.00   0.50    3.50    --   56.00  75.00 -54.14   92
 10  ω     33.00  58.00   0.50    3.50    --   56.00  75.00 140.09   50
 11  ω     32.00  78.00   0.50    3.50    --   60.00  75.00  38.59   92
 12  ω     78.00 105.00   0.50    3.50    --   64.00  74.00  -5.71   54
 13  ω     36.00  62.00   0.50    3.50    --   64.00  74.00  -5.71   52
 14  ω     36.00  62.00   0.50    3.50    --   64.00  75.00 160.93   52
 15  ω     41.00  66.00   0.50    3.50    --   68.00  75.00-145.27   50
 16  ω    118.00 156.00   0.50    3.50    --   68.00  75.00-175.51   76
 17  ω     40.00  66.00   0.50    3.50    --   68.00  75.00  71.69   52
 18  ω     41.00  76.00   0.50    3.50    --   68.00  75.00-175.51   70
 19  ω     45.00  72.00   0.50    3.50    --   72.00  75.00-136.55   54
 20  ω     46.00  74.00   0.50    3.50    --   72.00  69.00 -67.04   56
 21  ω     45.00  70.00   0.50    3.50    --   72.00  75.00 100.50   50
 22  ω     89.00 118.00   0.50    3.50    --   72.00  75.00-102.34   58
 23  ω     89.00 160.00   0.50    3.50    --   72.00  75.00 100.50  142
 24  ω     45.00  83.00   0.50    3.50    --   72.00  75.00-102.34   76
 25  ω     49.00  87.00   0.50    3.50    --   76.00  74.00   0.90   76
 26  ω     48.00  85.00   0.50    3.50    --   76.00  75.00 -57.50   74
 27  ω     62.00  90.00   0.50    3.50    --   84.00  61.00  65.09   56
 28  ω     59.00 118.00   0.50    3.50    --   84.00  66.00 126.50  118
 29  ω    142.00 167.00   0.50    3.50    --   84.00  66.00 126.50   50
 30  ω    134.00 172.00   0.50    3.50    --   84.00  74.00 119.41   76
 31  ω     57.00  84.00   0.50    3.50    --   84.00  74.00 119.41   54
 32  ω     57.00 173.00   0.50    3.50    --   84.00  72.00 -23.37  232
 33  ω     65.00 127.00   0.50    3.50    --   88.00  65.00-129.38  124
 34  ω     54.00 119.00   0.50    3.50    --   95.20 -61.00-120.00  130
 35  ω      6.00  44.00   0.50    3.50    --   95.20 -61.00-120.00   76
 36  ω     72.00 171.00   0.50    3.50    --   95.20  61.00  90.00  198
 37  ω     74.00 184.00   0.50    3.50    --   95.20  61.00  30.00  220
 38  ω     75.00 125.00   0.50    3.50    --   95.20 -82.00-180.00  100
 39  ω     94.00 124.00   0.50    3.50    --   95.20 -82.00 120.00   60
 40  ω     42.00  68.00   0.50    3.50    --   95.20 -82.00 120.00   52
 41  ω    116.00 178.00   0.50    3.50    --   95.20  61.00 -30.00  124
 42  ω     72.00 101.00   0.50    3.50    --   95.20  61.00 -30.00   58
 43  ω      7.00 125.00   0.50    3.50    --   95.20 -82.00  90.00  236
 44  ω    114.00 182.00   0.50    3.50    --   95.20  72.00 -71.24  136
 45  ω     68.00 109.00   0.50    3.50    --   95.20  72.00 -71.24   82
 46  ω    123.00 184.00   0.50    3.50    --   95.20  59.00 171.93  122
 47  ω     83.00 166.00   0.50    3.50    --   95.20  77.00   0.00  166
 48  ω     60.00 126.00   0.50    3.50    --   95.20 -82.00 -30.00  132
 49  ω     74.00 114.00   0.50    3.50    --   95.20  59.00 171.93   80
 50  ω    121.00 152.00   0.50    3.50    --   95.20  61.00-150.00   62
 51  ω     72.00 111.00   0.50    3.50    --   95.20  61.00-150.00   78
 52  ω    110.00 158.00   0.50    3.50    --   95.20  65.00  68.00   96
 53  ω     91.00 182.00   0.50    3.50    --   95.20  82.00 -90.00  182
 54  ω     73.00  98.00   0.50    3.50    --   95.20  65.00  68.00   50
 55  ω     72.00 184.00   0.50    3.50    --   95.20  61.00 150.00  224
 56  ω     71.00 157.00   0.50    3.50    --   95.20  68.00-100.36  172
 57  ω     94.00 121.00   0.50    3.50    --   95.20 -77.00  60.00   54
 58  ω     45.00 120.00   0.50    3.50    --   95.20 -82.00 -90.00  150
 59  ω     29.00  36.50   0.50    3.50    --   95.20 -77.00  60.00   15
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0890856000
_diffrn_orient_matrix_UB_12      0.1014406000
_diffrn_orient_matrix_UB_13      0.0242327000
_diffrn_orient_matrix_UB_21      -0.0860221000
_diffrn_orient_matrix_UB_22      0.0032289000
_diffrn_orient_matrix_UB_23      -0.0966421000
_diffrn_orient_matrix_UB_31      -0.0839604000
_diffrn_orient_matrix_UB_32      -0.0898310000
_diffrn_orient_matrix_UB_33      0.0876450000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                9071
_reflns_number_total             10544
_reflns_special_details          
;
 _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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         10544
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0633
_refine_ls_restrained_S_all      1.073
_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)+(0.1517P)²+0.4196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2135
_refine_ls_wR_factor_ref         0.2200
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4347(16)
 0.5653(16)
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) groups, All O(H,H) groups
3.a Free rotating group:
 O004(H00Q,H00R), O00C(H00S,H00U), O00D(H00V,H00W)
3.b Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00C), C00V(H00M,H00N), C00W(H00O,H00P), C00Y(H00G,H00H)
3.c Aromatic/amide H refined with riding coordinates:
 C00T(H00T), C00X(H00X)
3.d Idealised Me refined as rotating group:
 C00U(H00D,H00E,H00F), C00Z(H00I,H00J,H00K), C010(H01D,H01E,H01F), C011(H01G,
 H01H,H01I), C012(H01A,H01B,H01C), C013(H01J,H01K,H01L)
3.e Idealised tetrahedral OH refined as rotating group:
 O007(H007), O008(H008), O00A(H00L), O00B(H00B)
;
_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
O001 O -0.24842(15) 0.02492(15) 0.54325(14) 0.0251(4) Uani 1 1 d . . . . .
O002 O 0.67049(16) 0.19809(15) 0.99735(15) 0.0278(4) Uani 1 1 d . . . . .
O003 O 0.75240(15) 0.43919(15) 0.97130(15) 0.0258(4) Uani 1 1 d . . . . .
O004 O 0.22870(16) 0.02329(15) 0.99456(14) 0.0255(4) Uani 1 1 d . . . . .
H00Q H 0.1931 0.0113 1.0620 0.038 Uiso 1 1 d G . . . .
H00R H 0.2680 -0.0428 0.9958 0.038 Uiso 1 1 d G . . . .
O005 O 0.08064(16) 0.19666(16) 0.64462(14) 0.0264(4) Uani 1 1 d . . . . .
O006 O 0.39593(15) 0.33557(14) 0.83555(15) 0.0248(4) Uani 1 1 d . . . . .
O007 O 0.46233(18) 0.73945(15) 0.72863(16) 0.0307(4) Uani 1 1 d . . . . .
H007 H 0.5128 0.7817 0.7398 0.046 Uiso 1 1 calc GR . . . .
O008 O 0.03206(17) 0.26635(16) 0.24942(15) 0.0295(4) Uani 1 1 d . . . . .
H008 H -0.0117 0.2457 0.2084 0.044 Uiso 1 1 calc GR . . . .
O009 O -0.17004(17) 0.01191(15) 0.77861(14) 0.0281(4) Uani 1 1 d . . . . .
O00A O 0.39511(17) 0.17169(16) 0.99927(15) 0.0302(4) Uani 1 1 d . . . . .
H00L H 0.3472 0.1294 0.9848 0.045 Uiso 1 1 calc GR . . . .
O00B O 0.09036(18) 0.04348(15) 0.81697(16) 0.0312(4) Uani 1 1 d . . . . .
H00B H 0.1248 0.0664 0.8621 0.047 Uiso 1 1 calc GR . . . .
O00C O -0.09334(18) 0.20582(16) 0.10452(16) 0.0321(4) Uani 1 1 d . . . . .
H00S H -0.0885 0.1311 0.1310 0.048 Uiso 1 1 d G . . . .
H00U H -0.1642 0.2311 0.0717 0.048 Uiso 1 1 d G . . . .
O00D O 0.59995(19) 0.89425(17) 0.75926(16) 0.0336(4) Uani 1 1 d . . . . .
H00V H 0.5969 0.8745 0.8323 0.050 Uiso 1 1 d G . . . .
H00W H 0.6687 0.9281 0.7314 0.050 Uiso 1 1 d G . . . .
C00E C -0.0057(2) 0.2162(2) 0.3601(2) 0.0246(5) Uani 1 1 d . . . . .
C00F C -0.1506(2) 0.0948(2) 0.5038(2) 0.0221(5) Uani 1 1 d . . . . .
C00G C 0.5869(2) 0.2682(2) 0.93896(19) 0.0232(5) Uani 1 1 d . . . . .
C00H C -0.0841(2) 0.1173(2) 0.5883(2) 0.0221(5) Uani 1 1 d . . . . .
C00I C 0.4986(2) 0.6262(2) 0.7856(2) 0.0246(5) Uani 1 1 d . . . . .
C00J C 0.5746(2) 0.3929(2) 0.8956(2) 0.0225(5) Uani 1 1 d . . . . .
C00K C 0.4687(2) 0.2273(2) 0.9003(2) 0.0250(5) Uani 1 1 d . . . . .
C00L C 0.4620(2) 0.4280(2) 0.8336(2) 0.0241(5) Uani 1 1 d . . . . .
C00M C 0.0089(2) 0.1348(2) 0.7504(2) 0.0248(5) Uani 1 1 d . . . . .
C00N C -0.0476(2) 0.2256(2) 0.8074(2) 0.0276(5) Uani 1 1 d . . . . .
H00A H -0.0967 0.1863 0.8779 0.033 Uiso 1 1 calc R . . . .
H00C H -0.1076 0.2819 0.7566 0.033 Uiso 1 1 calc R . . . .
C00O C 0.0647(2) 0.2386(2) 0.4417(2) 0.0249(5) Uani 1 1 d . . . . .
C00P C 0.0213(2) 0.1869(2) 0.5541(2) 0.0237(5) Uani 1 1 d . . . . .
C00Q C 0.6483(2) 0.4795(2) 0.9062(2) 0.0228(5) Uani 1 1 d . . . . .
C00R C 0.4196(2) 0.5433(2) 0.7764(2) 0.0245(5) Uani 1 1 d . . . . .
C00S C -0.0957(2) 0.0785(2) 0.7103(2) 0.0235(5) Uani 1 1 d . . . . .
C00T C -0.1109(2) 0.1447(2) 0.3903(2) 0.0233(5) Uani 1 1 d . . . . .
H00T H -0.1533 0.1315 0.3329 0.028 Uiso 1 1 calc R . . . .
C00U C -0.3171(2) 0.0003(2) 0.4586(2) 0.0277(5) Uani 1 1 d . . . . .
H00D H -0.3611 0.0718 0.4118 0.042 Uiso 1 1 calc GR . . . .
H00E H -0.3795 -0.0550 0.4967 0.042 Uiso 1 1 calc GR . . . .
H00F H -0.2566 -0.0324 0.4108 0.042 Uiso 1 1 calc GR . . . .
C00V C 0.5017(3) 0.1521(2) 0.8216(2) 0.0296(5) Uani 1 1 d . . . . .
H00M H 0.5551 0.0820 0.8617 0.035 Uiso 1 1 calc R . . . .
H00N H 0.4219 0.1273 0.8053 0.035 Uiso 1 1 calc R . . . .
C00W C 0.2987(2) 0.5772(2) 0.7095(2) 0.0290(5) Uani 1 1 d . . . . .
H00O H 0.2536 0.6472 0.7222 0.035 Uiso 1 1 calc R . . . .
H00P H 0.2414 0.5144 0.7387 0.035 Uiso 1 1 calc R . . . .
C00X C 0.6101(2) 0.5966(2) 0.8505(2) 0.0243(5) Uani 1 1 d . . . . .
H00X H 0.6575 0.6554 0.8558 0.029 Uiso 1 1 calc R . . . .
C00Y C 0.1793(2) 0.3112(2) 0.4086(2) 0.0289(5) Uani 1 1 d . . . . .
H00G H 0.2304 0.2922 0.3458 0.035 Uiso 1 1 calc R . . . .
H00H H 0.2336 0.2899 0.4736 0.035 Uiso 1 1 calc R . . . .
C00Z C 0.0540(3) 0.2921(2) 0.8359(2) 0.0321(6) Uani 1 1 d . . . . .
H00I H 0.1025 0.3321 0.7665 0.048 Uiso 1 1 calc GR . . . .
H00J H 0.1119 0.2375 0.8887 0.048 Uiso 1 1 calc GR . . . .
H00K H 0.0117 0.3484 0.8704 0.048 Uiso 1 1 calc GR . . . .
C010 C 0.8243(2) 0.5258(2) 0.9887(2) 0.0286(5) Uani 1 1 d . . . . .
H01D H 0.8650 0.5699 0.9167 0.043 Uiso 1 1 calc GR . . . .
H01E H 0.8896 0.4876 1.0423 0.043 Uiso 1 1 calc GR . . . .
H01F H 0.7665 0.5781 1.0190 0.043 Uiso 1 1 calc GR . . . .
C011 C 0.5723(3) 0.2147(3) 0.7094(2) 0.0370(6) Uani 1 1 d . . . . .
H01G H 0.5926 0.1622 0.6648 0.055 Uiso 1 1 calc GR . . . .
H01H H 0.6512 0.2400 0.7247 0.055 Uiso 1 1 calc GR . . . .
H01I H 0.5182 0.2819 0.6671 0.055 Uiso 1 1 calc GR . . . .
C012 C 0.1418(3) 0.4435(3) 0.3717(3) 0.0433(7) Uani 1 1 d . . . . .
H01A H 0.0898 0.4657 0.3061 0.065 Uiso 1 1 calc GR . . . .
H01B H 0.2189 0.4846 0.3517 0.065 Uiso 1 1 calc GR . . . .
H01C H 0.0930 0.4634 0.4340 0.065 Uiso 1 1 calc GR . . . .
C013 C 0.3268(3) 0.6006(3) 0.5810(3) 0.0480(8) Uani 1 1 d . . . . .
H01J H 0.2481 0.6304 0.5420 0.072 Uiso 1 1 calc GR . . . .
H01K H 0.3604 0.5288 0.5670 0.072 Uiso 1 1 calc GR . . . .
H01L H 0.3896 0.6576 0.5528 0.072 Uiso 1 1 calc GR . . . .


_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
O001 C00F 1.347(3) . ?
O001 C00U 1.439(3) . ?
O002 C00G 1.241(3) . ?
O003 C00Q 1.355(3) . ?
O003 C010 1.431(3) . ?
O004 H00Q 0.8499 . ?
O004 H00R 0.8502 . ?
O005 C00M 1.455(3) . ?
O005 C00P 1.365(3) . ?
O006 C00K 1.457(3) . ?
O006 C00L 1.366(3) . ?
O007 H007 0.8200 . ?
O007 C00I 1.345(3) . ?
O008 H008 0.8200 . ?
O008 C00E 1.339(3) . ?
O009 C00S 1.235(3) . ?
O00A H00L 0.8200 . ?
O00A C00K 1.387(3) . ?
O00B H00B 0.8200 . ?
O00B C00M 1.390(3) . ?
O00C H00S 0.8503 . ?
O00C H00U 0.8502 . ?
O00D H00V 0.8499 . ?
O00D H00W 0.8498 . ?
C00E C00O 1.405(3) . ?
C00E C00T 1.414(3) . ?
C00F C00H 1.411(3) . ?
C00F C00T 1.372(3) . ?
C00G C00J 1.419(3) . ?
C00G C00K 1.541(3) . ?
C00H C00P 1.404(3) . ?
C00H C00S 1.417(3) . ?
C00I C00R 1.401(3) . ?
C00I C00X 1.414(3) . ?
C00J C00L 1.404(3) . ?
C00J C00Q 1.408(3) . ?
C00K C00V 1.523(3) . ?
C00L C00R 1.381(3) . ?
C00M C00N 1.522(3) . ?
C00M C00S 1.539(3) . ?
C00N H00A 0.9700 . ?
C00N H00C 0.9700 . ?
C00N C00Z 1.524(4) . ?
C00O C00P 1.374(3) . ?
C00O C00Y 1.504(3) . ?
C00Q C00X 1.384(3) . ?
C00R C00W 1.510(3) . ?
C00T H00T 0.9300 . ?
C00U H00D 0.9600 . ?
C00U H00E 0.9600 . ?
C00U H00F 0.9600 . ?
C00V H00M 0.9700 . ?
C00V H00N 0.9700 . ?
C00V C011 1.507(4) . ?
C00W H00O 0.9700 . ?
C00W H00P 0.9700 . ?
C00W C013 1.518(4) . ?
C00X H00X 0.9300 . ?
C00Y H00G 0.9700 . ?
C00Y H00H 0.9700 . ?
C00Y C012 1.526(4) . ?
C00Z H00I 0.9600 . ?
C00Z H00J 0.9600 . ?
C00Z H00K 0.9600 . ?
C010 H01D 0.9600 . ?
C010 H01E 0.9600 . ?
C010 H01F 0.9600 . ?
C011 H01G 0.9600 . ?
C011 H01H 0.9600 . ?
C011 H01I 0.9600 . ?
C012 H01A 0.9600 . ?
C012 H01B 0.9600 . ?
C012 H01C 0.9600 . ?
C013 H01J 0.9600 . ?
C013 H01K 0.9600 . ?
C013 H01L 0.9600 . ?

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
C00F O001 C00U 116.92(19) . . ?
C00Q O003 C010 116.76(19) . . ?
H00Q O004 H00R 104.5 . . ?
C00P O005 C00M 108.09(18) . . ?
C00L O006 C00K 107.99(17) . . ?
C00I O007 H007 109.5 . . ?
C00E O008 H008 109.5 . . ?
C00K O00A H00L 109.5 . . ?
C00M O00B H00B 109.5 . . ?
H00S O00C H00U 109.4 . . ?
H00V O00D H00W 109.5 . . ?
O008 C00E C00O 116.3(2) . . ?
O008 C00E C00T 120.5(2) . . ?
C00O C00E C00T 123.3(2) . . ?
O001 C00F C00H 116.0(2) . . ?
O001 C00F C00T 125.9(2) . . ?
C00T C00F C00H 118.2(2) . . ?
O002 C00G C00J 131.2(2) . . ?
O002 C00G C00K 122.5(2) . . ?
C00J C00G C00K 106.29(19) . . ?
C00F C00H C00S 133.3(2) . . ?
C00P C00H C00F 119.4(2) . . ?
C00P C00H C00S 107.3(2) . . ?
O007 C00I C00R 116.0(2) . . ?
O007 C00I C00X 120.3(2) . . ?
C00R C00I C00X 123.7(2) . . ?
C00L C00J C00G 107.8(2) . . ?
C00L C00J C00Q 119.1(2) . . ?
C00Q C00J C00G 133.0(2) . . ?
O006 C00K C00G 104.80(18) . . ?
O006 C00K C00V 107.81(19) . . ?
O00A C00K O006 109.13(18) . . ?
O00A C00K C00G 107.07(19) . . ?
O00A C00K C00V 112.8(2) . . ?
C00V C00K C00G 114.8(2) . . ?
O006 C00L C00J 113.1(2) . . ?
O006 C00L C00R 122.3(2) . . ?
C00R C00L C00J 124.6(2) . . ?
O005 C00M C00N 107.36(19) . . ?
O005 C00M C00S 104.41(18) . . ?
O00B C00M O005 109.02(18) . . ?
O00B C00M C00N 115.2(2) . . ?
O00B C00M C00S 107.18(19) . . ?
C00N C00M C00S 113.06(19) . . ?
C00M C00N H00A 108.8 . . ?
C00M C00N H00C 108.8 . . ?
C00M C00N C00Z 114.0(2) . . ?
H00A C00N H00C 107.7 . . ?
C00Z C00N H00A 108.8 . . ?
C00Z C00N H00C 108.8 . . ?
C00E C00O C00Y 122.7(2) . . ?
C00P C00O C00E 114.3(2) . . ?
C00P C00O C00Y 123.0(2) . . ?
O005 C00P C00H 113.2(2) . . ?
O005 C00P C00O 122.2(2) . . ?
C00O C00P C00H 124.6(2) . . ?
O003 C00Q C00J 115.8(2) . . ?
O003 C00Q C00X 125.6(2) . . ?
C00X C00Q C00J 118.6(2) . . ?
C00I C00R C00W 122.8(2) . . ?
C00L C00R C00I 114.2(2) . . ?
C00L C00R C00W 122.9(2) . . ?
O009 C00S C00H 130.8(2) . . ?
O009 C00S C00M 122.5(2) . . ?
C00H C00S C00M 106.8(2) . . ?
C00E C00T H00T 119.8 . . ?
C00F C00T C00E 120.3(2) . . ?
C00F C00T H00T 119.8 . . ?
O001 C00U H00D 109.5 . . ?
O001 C00U H00E 109.5 . . ?
O001 C00U H00F 109.5 . . ?
H00D C00U H00E 109.5 . . ?
H00D C00U H00F 109.5 . . ?
H00E C00U H00F 109.5 . . ?
C00K C00V H00M 108.9 . . ?
C00K C00V H00N 108.9 . . ?
H00M C00V H00N 107.7 . . ?
C011 C00V C00K 113.5(2) . . ?
C011 C00V H00M 108.9 . . ?
C011 C00V H00N 108.9 . . ?
C00R C00W H00O 109.0 . . ?
C00R C00W H00P 109.0 . . ?
C00R C00W C013 113.1(2) . . ?
H00O C00W H00P 107.8 . . ?
C013 C00W H00O 109.0 . . ?
C013 C00W H00P 109.0 . . ?
C00I C00X H00X 120.2 . . ?
C00Q C00X C00I 119.6(2) . . ?
C00Q C00X H00X 120.2 . . ?
C00O C00Y H00G 108.8 . . ?
C00O C00Y H00H 108.8 . . ?
C00O C00Y C012 113.6(2) . . ?
H00G C00Y H00H 107.7 . . ?
C012 C00Y H00G 108.8 . . ?
C012 C00Y H00H 108.8 . . ?
C00N C00Z H00I 109.5 . . ?
C00N C00Z H00J 109.5 . . ?
C00N C00Z H00K 109.5 . . ?
H00I C00Z H00J 109.5 . . ?
H00I C00Z H00K 109.5 . . ?
H00J C00Z H00K 109.5 . . ?
O003 C010 H01D 109.5 . . ?
O003 C010 H01E 109.5 . . ?
O003 C010 H01F 109.5 . . ?
H01D C010 H01E 109.5 . . ?
H01D C010 H01F 109.5 . . ?
H01E C010 H01F 109.5 . . ?
C00V C011 H01G 109.5 . . ?
C00V C011 H01H 109.5 . . ?
C00V C011 H01I 109.5 . . ?
H01G C011 H01H 109.5 . . ?
H01G C011 H01I 109.5 . . ?
H01H C011 H01I 109.5 . . ?
C00Y C012 H01A 109.5 . . ?
C00Y C012 H01B 109.5 . . ?
C00Y C012 H01C 109.5 . . ?
H01A C012 H01B 109.5 . . ?
H01A C012 H01C 109.5 . . ?
H01B C012 H01C 109.5 . . ?
C00W C013 H01J 109.5 . . ?
C00W C013 H01K 109.5 . . ?
C00W C013 H01L 109.5 . . ?
H01J C013 H01K 109.5 . . ?
H01J C013 H01L 109.5 . . ?
H01K C013 H01L 109.5 . . ?

_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 1.463
_oxdiff_exptl_absorpt_empirical_full_min 0.701
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.4347(16) 23178 3098 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.5653(16) 23269 3098 nmt -1.0008 0.0000 0.0002 -0.0277 0.0162 -0.9835 0.0277
-1.0172 -0.0161

_twin_special_details            
;
Component 2 rotated by 179.9968° 
 around [-0.00 0.71 -0.71] (reciprocal) or [-0.02 0.72 -0.69] (direct)
;
####################################################################### 
# 
# 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_huangyanbing_sh31-fr1-m2_collect
_database_code_depnum_ccdc_archive 'CCDC 2072134'
loop_
_audit_author_name
_audit_author_address
'Lu Wang'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;
_audit_creation_date             2019-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13.84 O4'
_chemical_formula_sum            'C13 H14 O4'
_chemical_formula_weight         234.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C52 H56 O16 '
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1797(3)
_cell_length_b                   5.27290(10)
_cell_length_c                   17.2041(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.215(2)
_cell_angle_gamma                90
_cell_volume                     1090.63(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5498
_cell_measurement_temperature    99.98(16)
_cell_measurement_theta_max      78.8090
_cell_measurement_theta_min      5.1980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6947
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.170
_diffrn_reflns_theta_min         3.677
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  31.00   0.40    1.07    --    0.00 -82.00  60.00  160
  2  ω    -33.00  31.00   0.40    1.07    --    0.00 -82.00-150.00  160
  3  ω    -33.00  31.00   0.40    1.07    --    0.00 -82.00   0.00  160
  4  ω    -33.00  31.00   0.40    1.07    --    0.00 -82.00 120.00  160
  5  ω     17.00 129.00   0.40    4.29    --  106.20 -15.00  60.00  280
  6  ω     17.00 129.00   0.40    4.29    --  106.20 -61.00 -60.00  280
  7  ω     88.00 196.00   0.40    4.29    --  106.20  82.00  60.00  270
  8  ω     90.00 196.00   0.40    4.29    --  106.20  30.00-120.00  265
  9  ω     17.00 125.00   0.40    4.29    --  106.20 -45.00 -60.00  270
 10  ω     90.00 196.00   0.40    4.29    --  106.20  30.00-180.00  265
 11  ω     92.00 160.80   0.40    4.29    --  106.20  15.00 -30.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0615608000
_diffrn_orient_matrix_UB_12      -0.1073379000
_diffrn_orient_matrix_UB_13      0.0782874000
_diffrn_orient_matrix_UB_21      -0.0966782000
_diffrn_orient_matrix_UB_22      0.0845421000
_diffrn_orient_matrix_UB_23      0.0417854000
_diffrn_orient_matrix_UB_31      -0.0573422000
_diffrn_orient_matrix_UB_32      -0.2581995000
_diffrn_orient_matrix_UB_33      -0.0188155000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                2204
_reflns_number_total             2311
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.128
_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)+(0.0523P)²+0.8040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1263
_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
 C10A-C11A
 1.5 with sigma of 0.02
 C17-C10A
 1.5 with sigma of 0.02
3. Others
 Sof(H17a)=Sof(H17b)=Sof(H17c)=FVAR(1)
 Sof(C10A)=Sof(H10A)=1-FVAR(2)
 Sof(C10)=Sof(H10)=FVAR(2)
 Sof(C11A)=Sof(H11c)=Sof(H11d)=1-FVAR(3)
 Sof(C11)=Sof(H11a)=Sof(H11b)=FVAR(3)
4.a Ternary CH refined with riding coordinates:
 C10(H10), C10A(H10A)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C5(H5a,H5b), C11(H11a,H11b), C11A(H11c,H11d)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2)
4.d Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C15(H15a,H15b,H15c)
;
_atom_sites_solution_hydrogens   geom
_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 0.62478(9) 0.3259(2) 0.55450(6) 0.0232(3) Uani 1 1 d . . . . .
O14 O 0.83761(10) 1.0142(2) 0.68622(6) 0.0262(3) Uani 1 1 d . . . . .
O4 O 0.89871(9) 0.6935(2) 0.43568(7) 0.0269(3) Uani 1 1 d . . . . .
O16 O 0.68431(11) 0.7704(3) 0.75213(7) 0.0364(3) Uani 1 1 d . . . . .
C8 C 0.70597(12) 0.5049(3) 0.56037(9) 0.0204(3) Uani 1 1 d . . . . .
C1 C 0.81574(13) 0.8573(3) 0.62322(9) 0.0216(3) Uani 1 1 d . . . . .
C13 C 0.73037(12) 0.6728(3) 0.62540(9) 0.0211(3) Uani 1 1 d . . . . .
C3 C 0.84776(13) 0.6967(3) 0.50023(9) 0.0220(3) Uani 1 1 d . . . . .
C7 C 0.76610(13) 0.5149(3) 0.49851(9) 0.0217(3) Uani 1 1 d . . . . .
C2 C 0.87449(13) 0.8726(3) 0.56049(9) 0.0231(3) Uani 1 1 d . . . . .
H2 H 0.929151 0.994777 0.558893 0.028 Uiso 1 1 calc R . . . .
C6 C 0.75633(13) 0.3698(3) 0.42231(9) 0.0243(3) Uani 1 1 d . . . . .
H6A H 0.687619 0.409456 0.387581 0.029 Uiso 1 1 calc R . . . .
H6B H 0.760720 0.188275 0.431352 0.029 Uiso 1 1 calc R . . . .
C5 C 0.85804(13) 0.4685(3) 0.38929(9) 0.0264(4) Uani 1 1 d . . . . .
H5A H 0.915445 0.339391 0.393798 0.032 Uiso 1 1 calc R . . . .
H5B H 0.837482 0.513038 0.334171 0.032 Uiso 1 1 calc R . . . .
C17 C 0.46880(14) 0.1270(3) 0.59595(10) 0.0272(4) Uani 1 1 d D . . . .
H17A H 0.430263 0.115870 0.542824 0.041 Uiso 0.95(2) 1 calc GR . P A 1
H17B H 0.415719 0.137824 0.631478 0.041 Uiso 0.95(2) 1 calc GR . P A 1
H17C H 0.514152 -0.021159 0.608036 0.041 Uiso 0.95(2) 1 calc GR . P A 1
C12 C 0.67160(14) 0.6384(3) 0.69308(9) 0.0265(4) Uani 1 1 d . . . . .
C15 C 0.92468(14) 1.1963(3) 0.68636(10) 0.0275(4) Uani 1 1 d . . . . .
H15A H 0.905494 1.310940 0.642969 0.041 Uiso 1 1 calc GR . . . .
H15B H 0.992690 1.110385 0.681349 0.041 Uiso 1 1 calc GR . . . .
H15C H 0.934301 1.289736 0.734868 0.041 Uiso 1 1 calc GR . . . .
C10 C 0.5414(3) 0.3597(6) 0.60457(19) 0.0213(7) Uani 0.797(12) 1 d . . P B 1
H10 H 0.495791 0.507731 0.586353 0.026 Uiso 0.797(12) 1 calc R . P B 1
C11 C 0.5975(4) 0.4054(8) 0.68813(18) 0.0249(8) Uani 0.811(14) 1 d . . P B 1
H11A H 0.641834 0.258493 0.706940 0.030 Uiso 0.811(14) 1 calc R . P B 1
H11B H 0.541432 0.428677 0.721705 0.030 Uiso 0.811(14) 1 calc R . P B 1
C10A C 0.5801(12) 0.269(3) 0.6264(8) 0.031(4) Uani 0.203(12) 1 d D . P B 2
H10A H 0.630911 0.153595 0.659429 0.037 Uiso 0.203(12) 1 calc R . P B 2
C11A C 0.5613(14) 0.494(3) 0.6719(8) 0.026(3) Uani 0.189(14) 1 d D . P B 2
H11C H 0.533553 0.445289 0.719497 0.031 Uiso 0.189(14) 1 calc R . P B 2
H11D H 0.506246 0.602417 0.641088 0.031 Uiso 0.189(14) 1 calc R . P B 2


_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 C8 1.3589(19) . ?
O9 C10 1.444(2) . ?
O9 C10A 1.461(11) . ?
O14 C1 1.3557(19) . ?
O14 C15 1.4303(19) . ?
O4 C3 1.3562(18) . ?
O4 C5 1.471(2) . ?
O16 C12 1.221(2) . ?
C8 C13 1.420(2) . ?
C8 C7 1.386(2) . ?
C1 C13 1.429(2) . ?
C1 C2 1.389(2) . ?
C13 C12 1.472(2) . ?
C3 C7 1.379(2) . ?
C3 C2 1.390(2) . ?
C7 C6 1.506(2) . ?
C2 H2 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.534(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 C10 1.506(3) . ?
C17 C10A 1.563(10) . ?
C12 C11 1.519(3) . ?
C12 C11A 1.536(11) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C11 1.509(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10A H10A 0.9800 . ?
C10A C11A 1.462(15) . ?
C11A H11C 0.9700 . ?
C11A H11D 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
C8 O9 C10 116.30(13) . . ?
C8 O9 C10A 116.5(4) . . ?
C1 O14 C15 117.50(12) . . ?
C3 O4 C5 107.22(12) . . ?
O9 C8 C13 123.33(13) . . ?
O9 C8 C7 115.91(13) . . ?
C7 C8 C13 120.76(14) . . ?
O14 C1 C13 116.43(13) . . ?
O14 C1 C2 121.72(14) . . ?
C2 C1 C13 121.84(14) . . ?
C8 C13 C1 117.71(14) . . ?
C8 C13 C12 118.64(14) . . ?
C1 C13 C12 123.55(14) . . ?
O4 C3 C7 113.38(14) . . ?
O4 C3 C2 122.40(14) . . ?
C7 C3 C2 124.19(14) . . ?
C8 C7 C6 132.17(15) . . ?
C3 C7 C8 118.56(14) . . ?
C3 C7 C6 109.15(13) . . ?
C1 C2 C3 116.89(14) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C7 C6 H6A 111.5 . . ?
C7 C6 H6B 111.5 . . ?
C7 C6 C5 101.21(13) . . ?
H6A C6 H6B 109.3 . . ?
C5 C6 H6A 111.5 . . ?
C5 C6 H6B 111.5 . . ?
O4 C5 C6 107.12(12) . . ?
O4 C5 H5A 110.3 . . ?
O4 C5 H5B 110.3 . . ?
C6 C5 H5A 110.3 . . ?
C6 C5 H5B 110.3 . . ?
H5A C5 H5B 108.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
O16 C12 C13 125.10(15) . . ?
O16 C12 C11 120.19(16) . . ?
O16 C12 C11A 118.0(4) . . ?
C13 C12 C11 114.52(15) . . ?
C13 C12 C11A 113.0(4) . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O9 C10 C17 107.38(17) . . ?
O9 C10 H10 108.9 . . ?
O9 C10 C11 109.5(3) . . ?
C17 C10 H10 108.9 . . ?
C17 C10 C11 113.2(2) . . ?
C11 C10 H10 108.9 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 C12 110.9(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.0 . . ?
O9 C10A C17 103.6(7) . . ?
O9 C10A H10A 109.4 . . ?
O9 C10A C11A 113.3(11) . . ?
C17 C10A H10A 109.4 . . ?
C11A C10A C17 111.5(10) . . ?
C11A C10A H10A 109.4 . . ?
C12 C11A H11C 109.9 . . ?
C12 C11A H11D 109.9 . . ?
C10A C11A C12 108.9(10) . . ?
C10A C11A H11C 109.9 . . ?
C10A C11A H11D 109.9 . . ?
H11C C11A H11D 108.3 . . ?

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
O9 C8 C13 C1 -178.21(13) . . . . ?
O9 C8 C13 C12 5.3(2) . . . . ?
O9 C8 C7 C3 178.42(13) . . . . ?
O9 C8 C7 C6 2.9(2) . . . . ?
O9 C10 C11 C12 58.9(4) . . . . ?
O9 C10A C11A C12 -58.1(17) . . . . ?
O14 C1 C13 C8 -179.70(13) . . . . ?
O14 C1 C13 C12 -3.4(2) . . . . ?
O14 C1 C2 C3 177.87(14) . . . . ?
O4 C3 C7 C8 -178.13(13) . . . . ?
O4 C3 C7 C6 -1.63(19) . . . . ?
O4 C3 C2 C1 179.54(14) . . . . ?
O16 C12 C11 C10 147.7(2) . . . . ?
O16 C12 C11A C10A -153.4(10) . . . . ?
C8 O9 C10 C17 -173.27(19) . . . . ?
C8 O9 C10 C11 -50.1(3) . . . . ?
C8 O9 C10A C17 163.4(6) . . . . ?
C8 O9 C10A C11A 42.4(15) . . . . ?
C8 C13 C12 O16 -179.44(17) . . . . ?
C8 C13 C12 C11 5.5(3) . . . . ?
C8 C13 C12 C11A -22.3(9) . . . . ?
C8 C7 C6 C5 -174.80(16) . . . . ?
C1 C13 C12 O16 4.3(3) . . . . ?
C1 C13 C12 C11 -170.7(3) . . . . ?
C1 C13 C12 C11A 161.5(9) . . . . ?
C13 C8 C7 C3 -2.1(2) . . . . ?
C13 C8 C7 C6 -177.59(15) . . . . ?
C13 C1 C2 C3 -1.1(2) . . . . ?
C13 C12 C11 C10 -37.0(4) . . . . ?
C13 C12 C11A C10A 47.7(15) . . . . ?
C3 O4 C5 C6 13.24(16) . . . . ?
C3 C7 C6 C5 9.35(17) . . . . ?
C7 C8 C13 C1 2.3(2) . . . . ?
C7 C8 C13 C12 -174.14(14) . . . . ?
C7 C3 C2 C1 1.4(2) . . . . ?
C7 C6 C5 O4 -13.39(16) . . . . ?
C2 C1 C13 C8 -0.7(2) . . . . ?
C2 C1 C13 C12 175.56(15) . . . . ?
C2 C3 C7 C8 0.2(2) . . . . ?
C2 C3 C7 C6 176.65(14) . . . . ?
C5 O4 C3 C7 -7.44(18) . . . . ?
C5 O4 C3 C2 174.24(14) . . . . ?
C17 C10 C11 C12 178.7(3) . . . . ?
C17 C10A C11A C12 -174.5(12) . . . . ?
C15 O14 C1 C13 178.44(13) . . . . ?
C15 O14 C1 C2 -0.6(2) . . . . ?
C10 O9 C8 C13 18.2(3) . . . . ?
C10 O9 C8 C7 -162.3(2) . . . . ?
C10A O9 C8 C13 -14.5(10) . . . . ?
C10A O9 C8 C7 165.0(10) . . . . ?

_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 2.321
_oxdiff_exptl_absorpt_empirical_full_min 0.498
####################################################################### 
# 
# 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_zahngwenjun_sh31-10_collect
_database_code_depnum_ccdc_archive 'CCDC 2072139'
loop_
_audit_author_name
_audit_author_address
'Lu Wang'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;
_audit_creation_date             2019-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H18 O6), H2 O'
_chemical_formula_sum            'C26 H38 O13'
_chemical_formula_weight         558.56
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C216 H352 N16 O80 '
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        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.3741(4)
_cell_length_b                   13.2115(2)
_cell_length_c                   17.7270(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.7810(10)
_cell_angle_gamma                90
_cell_volume                     5377.60(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15666
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      73.6780
_cell_measurement_theta_min      4.2090
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2384
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29267
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.159
_diffrn_reflns_theta_min         3.850
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  -2.00   0.50    0.50    --    0.00 -82.00  60.00   62
  2  ω    -15.00  59.00   0.50    0.50    --    0.00  38.00  60.00  148
  3  ω      9.00  87.00   0.50    0.50    --    0.00  38.00-120.00  156
  4  ω    -88.00 -14.00   0.50    0.50    --    0.00 -19.00  90.00  148
  5  ω     13.00  49.00   0.50    1.50    --   95.20 -82.00 120.00   72
  6  ω     88.00 126.00   0.50    1.50    --   95.20 -82.00 120.00   76
  7  ω     78.00 184.00   0.50    1.50    --   95.20  44.00 -78.88  212
  8  ω     73.00 100.00   0.50    1.50    --   95.20  61.00 -90.00   54
  9  ω    135.00 184.00   0.50    1.50    --   95.20  77.00  90.00   98
 10  ω      7.00 126.00   0.50    1.50    --   95.20 -82.00  60.00  238
 11  ω     73.00 183.00   0.50    1.50    --   95.20  61.00 -30.00  220
 12  ω      7.00  95.00   0.50    1.50    --   95.20 -61.00-180.00  176
 13  ω      9.00  63.00   0.50    1.50    --   95.20 -61.00 -90.00  108
 14  ω     64.00 112.00   0.50    1.50    --   95.20 -61.00 -90.00   96
 15  ω     66.00 101.00   0.50    1.50    --   95.20 -82.00-180.00   70
 16  ω     16.00 119.00   0.50    1.50    --   95.20 -82.00 -90.00  206
 17  ω     79.00 162.00   0.50    1.50    --   95.20  30.00  60.00  166
 18  ω     10.00 119.00   0.50    1.50    --   95.20 -61.00  60.00  218
 19  ω     79.00 185.00   0.50    1.50    --   95.20  30.00  30.00  212
 20  ω    134.00 172.00   0.50    1.50    --   95.20  71.00 -92.33   76
 21  ω     82.00 107.00   0.50    1.50    --   95.20 -82.00-150.00   50
 22  ω     69.00  96.00   0.50    1.50    --   95.20  71.00 -92.33   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0622270000
_diffrn_orient_matrix_UB_12      -0.0359912000
_diffrn_orient_matrix_UB_13      -0.0335943000
_diffrn_orient_matrix_UB_21      0.0237999000
_diffrn_orient_matrix_UB_22      -0.1053429000
_diffrn_orient_matrix_UB_23      -0.0152650000
_diffrn_orient_matrix_UB_31      -0.0077374000
_diffrn_orient_matrix_UB_32      -0.0350252000
_diffrn_orient_matrix_UB_33      0.0803493000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                4974
_reflns_number_total             5403
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         5403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0701
_refine_ls_restrained_S_all      1.081
_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)+(0.0857P)²+12.4774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1920
_refine_ls_wR_factor_ref         0.1945
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Others
 Sof(H00a)=Sof(H00i)=Sof(H00j)=Sof(C0)=Sof(H0)=Sof(C1)=Sof(H1a)=Sof(H1b)=
 Sof(H1c)=1-FVAR(1)
 Sof(H00C)=Sof(H00g)=Sof(H00h)=Sof(C011)=Sof(H011)=Sof(C013)=Sof(H01a)=
 Sof(H01b)=Sof(H01c)=FVAR(1)
3.a Free rotating group:
 O00D(H00z,H)
3.b Ternary CH refined with riding coordinates:
 C010(H010), C011(H011), C0(H0)
3.c Secondary CH2 refined with riding coordinates:
 C00R(H00q,H00r), C00S(H00s,H00t), C00U(H00g,H00h), C00U(H00i,H00j), C00W(H00k,
 H00m), C00X(H00n,H00o), C00Z(H00x,H00y)
3.d Aromatic/amide H refined with riding coordinates:
 C00J(H00p), C00L(H00L)
3.e Tetrahedral OH refined with riding coordinates:
 O00C(H00C), O00C(H00a)
3.f Idealised Me refined as rotating group:
 C00T(H00d,H00e,H00f), C00Y(H00u,H00v,H00w), C012(H01d,H01e,H01f), C013(H01a,
 H01b,H01c), C1(H1a,H1b,H1c)
3.g Idealised tetrahedral OH refined as rotating group:
 O002(H002), O004(H004), O005(H005), O007(H007), O008(H008), O009(H009),
 O00B(H00B)
;
_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
O001 O 0.55318(8) 0.19041(13) 0.68640(10) 0.0392(4) Uani 1 1 d . . . . .
O002 O 0.60360(8) 0.54247(14) 0.71356(11) 0.0422(4) Uani 1 1 d . . . . .
H002 H 0.635573 0.518114 0.731212 0.063 Uiso 1 1 calc GR . . . .
O003 O 0.29344(8) 0.63848(13) 0.42453(10) 0.0400(4) Uani 1 1 d . . . . .
O004 O 0.24315(8) 0.98978(13) 0.40519(11) 0.0425(4) Uani 1 1 d . . . . .
H004 H 0.212324 0.966376 0.382070 0.064 Uiso 1 1 calc GR . . . .
O005 O 0.43438(8) 0.89668(14) 0.50774(12) 0.0449(5) Uani 1 1 d . . . . .
H005 H 0.455361 0.846773 0.517147 0.067 Uiso 1 1 calc GR . . . .
O006 O 0.16939(8) 0.85909(15) 0.35961(11) 0.0450(5) Uani 1 1 d . . . . .
O007 O 0.50795(9) 0.74928(14) 0.55171(12) 0.0463(5) Uani 1 1 d . . . . .
H007 H 0.523491 0.777909 0.591318 0.070 Uiso 1 1 calc GR . . . .
O008 O 0.41782(8) 0.45058(14) 0.58681(11) 0.0424(4) Uani 1 1 d . . . . .
H008 H 0.400022 0.401229 0.566431 0.064 Uiso 1 1 calc GR . . . .
O009 O 0.73218(9) 0.28500(16) 0.88043(12) 0.0484(5) Uani 1 1 d . . . . .
H009 H 0.714896 0.254771 0.909800 0.073 Uiso 1 1 calc GR . . . .
O00A O 0.67638(8) 0.41115(15) 0.76309(12) 0.0497(5) Uani 1 1 d . . . . .
O00B O 0.37948(9) 1.19769(14) 0.39480(12) 0.0474(5) Uani 1 1 d . . . . .
H00B H 0.380332 1.219793 0.351799 0.071 Uiso 1 1 calc GR . . . .
O00C O 0.10796(10) 0.73804(15) 0.24956(12) 0.0560(6) Uani 1 1 d . . . . .
H00C H 0.109433 0.799126 0.257868 0.084 Uiso 0.856(8) 1 calc R . P A 1
H00A H 0.120755 0.788357 0.274130 0.084 Uiso 0.144(8) 1 calc R . P A 2
O00D O 0.35117(10) 0.30031(19) 0.52564(15) 0.0619(6) Uani 1 1 d . . . . .
H00Z H 0.317556 0.300181 0.537545 0.093 Uiso 1 1 d G . . . .
H H 0.350746 0.263134 0.486358 0.093 Uiso 1 1 d G . . . .
C00E C 0.53861(11) 0.28980(18) 0.67383(13) 0.0332(5) Uani 1 1 d . . . . .
C00F C 0.58177(11) 0.36344(19) 0.70287(13) 0.0342(5) Uani 1 1 d . . . . .
C00G C 0.47082(11) 0.42133(19) 0.62440(13) 0.0347(5) Uani 1 1 d . . . . .
C00H C 0.51048(11) 0.49721(19) 0.65173(13) 0.0341(5) Uani 1 1 d . . . . .
C00I C 0.56533(11) 0.46714(19) 0.68951(13) 0.0347(5) Uani 1 1 d . . . . .
C00J C 0.48436(11) 0.31842(19) 0.63492(14) 0.0347(5) Uani 1 1 d . . . . .
H00P H 0.456834 0.269543 0.615703 0.042 Uiso 1 1 calc R . . . .
C00K C 0.30958(11) 0.73647(19) 0.43495(13) 0.0349(5) Uani 1 1 d . . . . .
C00L C 0.36545(11) 0.76497(19) 0.46619(14) 0.0359(5) Uani 1 1 d . . . . .
H00L H 0.393881 0.715740 0.480291 0.043 Uiso 1 1 calc R . . . .
C00M C 0.28197(12) 0.9139(2) 0.42479(14) 0.0376(5) Uani 1 1 d . . . . .
C00N C 0.26501(11) 0.81098(19) 0.41183(14) 0.0358(5) Uani 1 1 d . . . . .
C00O C 0.20542(11) 0.7880(2) 0.37606(14) 0.0373(5) Uani 1 1 d . . . . .
C00P C 0.33840(12) 0.94340(19) 0.45724(14) 0.0383(6) Uani 1 1 d . . . . .
C00Q C 0.38007(11) 0.8672(2) 0.47705(14) 0.0378(5) Uani 1 1 d . . . . .
C00R C 0.51179(12) 0.64193(19) 0.56275(16) 0.0398(6) Uani 1 1 d . . . . .
H00Q H 0.551288 0.620323 0.561680 0.048 Uiso 1 1 calc R . . . .
H00R H 0.486191 0.609042 0.520468 0.048 Uiso 1 1 calc R . . . .
C00S C 0.49552(11) 0.60764(19) 0.63791(14) 0.0377(5) Uani 1 1 d . . . . .
H00S H 0.516471 0.647863 0.679946 0.045 Uiso 1 1 calc R . . . .
H00T H 0.454135 0.617605 0.635801 0.045 Uiso 1 1 calc R . . . .
C00T C 0.33556(12) 0.56237(19) 0.45415(16) 0.0411(6) Uani 1 1 d . . . . .
H00D H 0.365650 0.560984 0.423989 0.062 Uiso 1 1 calc GR . . . .
H00E H 0.316833 0.497471 0.451720 0.062 Uiso 1 1 calc GR . . . .
H00F H 0.352344 0.577794 0.506536 0.062 Uiso 1 1 calc GR . . . .
C00U C 0.18340(12) 0.6831(2) 0.35607(16) 0.0410(6) Uani 1 1 d . . . . .
H00G H 0.190634 0.641209 0.401819 0.049 Uiso 0.856(8) 1 calc R . P A 1
H00H H 0.204424 0.654001 0.319036 0.049 Uiso 0.856(8) 1 calc R . P A 1
H00I H 0.170317 0.656814 0.401054 0.049 Uiso 0.144(8) 1 calc R . P A 2
H00J H 0.216943 0.642929 0.349828 0.049 Uiso 0.144(8) 1 calc R . P A 2
C00V C 0.64052(11) 0.3410(2) 0.74392(15) 0.0396(6) Uani 1 1 d . . . . .
C00W C 0.35380(13) 1.0539(2) 0.46567(16) 0.0431(6) Uani 1 1 d . . . . .
H00K H 0.388163 1.062951 0.505242 0.052 Uiso 1 1 calc R . . . .
H00M H 0.321967 1.091479 0.480345 0.052 Uiso 1 1 calc R . . . .
C00X C 0.36532(12) 1.0919(2) 0.38968(17) 0.0442(6) Uani 1 1 d . . . . .
H00N H 0.397329 1.054273 0.375496 0.053 Uiso 1 1 calc R . . . .
H00O H 0.331073 1.081325 0.350173 0.053 Uiso 1 1 calc R . . . .
C00Y C 0.51067(12) 0.11636(19) 0.65518(16) 0.0427(6) Uani 1 1 d . . . . .
H00U H 0.501108 0.123956 0.600403 0.064 Uiso 1 1 calc GR . . . .
H00V H 0.476230 0.125575 0.676612 0.064 Uiso 1 1 calc GR . . . .
H00W H 0.526125 0.049825 0.667551 0.064 Uiso 1 1 calc GR . . . .
C00Z C 0.66140(12) 0.2358(2) 0.76552(17) 0.0443(6) Uani 1 1 d . . . . .
H00X H 0.657427 0.195035 0.719312 0.053 Uiso 1 1 calc R . . . .
H00Y H 0.636733 0.206223 0.798010 0.053 Uiso 1 1 calc R . . . .
C010 C 0.72435(13) 0.2316(2) 0.80744(18) 0.0487(7) Uani 1 1 d . . . . .
H010 H 0.748804 0.264111 0.775200 0.058 Uiso 1 1 calc R . . . .
C011 C 0.11844(15) 0.6832(2) 0.3226(2) 0.0384(9) Uani 0.856(8) 1 d . . P A 1
H011 H 0.097328 0.716407 0.358622 0.046 Uiso 0.856(8) 1 calc R . P A 1
C012 C 0.74502(15) 0.1248(3) 0.8228(2) 0.0606(8) Uani 1 1 d . . . . .
H01D H 0.784870 0.125238 0.849029 0.091 Uiso 1 1 calc GR . . . .
H01E H 0.742034 0.089177 0.775062 0.091 Uiso 1 1 calc GR . . . .
H01F H 0.721387 0.091729 0.854242 0.091 Uiso 1 1 calc GR . . . .
C013 C 0.09607(15) 0.5766(2) 0.3074(2) 0.0455(9) Uani 0.856(8) 1 d . . P A 1
H01A H 0.055379 0.578482 0.285059 0.068 Uiso 0.856(8) 1 calc GR . P A 1
H01B H 0.101500 0.539713 0.354890 0.068 Uiso 0.856(8) 1 calc GR . P A 1
H01C H 0.117116 0.543869 0.272708 0.068 Uiso 0.856(8) 1 calc GR . P A 1
C0 C 0.1325(9) 0.6575(16) 0.2833(14) 0.048(6) Uani 0.144(8) 1 d . . P A 2
H0 H 0.138810 0.600235 0.250643 0.057 Uiso 0.144(8) 1 calc R . P A 2
C1 C 0.0772(9) 0.6530(18) 0.3245(15) 0.057(7) Uani 0.144(8) 1 d . . P A 2
H1A H 0.078956 0.708175 0.360121 0.086 Uiso 0.144(8) 1 calc GR . P A 2
H1B H 0.077353 0.590050 0.351598 0.086 Uiso 0.144(8) 1 calc GR . P A 2
H1C H 0.042175 0.658071 0.286578 0.086 Uiso 0.144(8) 1 calc GR . P A 2


_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
O001 C00E 1.364(3) . ?
O001 C00Y 1.430(3) . ?
O002 H002 0.8200 . ?
O002 C00I 1.353(3) . ?
O003 C00K 1.351(3) . ?
O003 C00T 1.436(3) . ?
O004 H004 0.8200 . ?
O004 C00M 1.353(3) . ?
O005 H005 0.8200 . ?
O005 C00Q 1.342(3) . ?
O006 C00O 1.259(3) . ?
O007 H007 0.8200 . ?
O007 C00R 1.432(3) . ?
O008 H008 0.8200 . ?
O008 C00G 1.349(3) . ?
O009 H009 0.8200 . ?
O009 C010 1.455(4) . ?
O00A C00V 1.253(3) . ?
O00B H00B 0.8200 . ?
O00B C00X 1.435(3) . ?
O00C H00C 0.8200 . ?
O00C H00A 0.8200 . ?
O00C C011 1.464(4) . ?
O00C C0 1.300(19) . ?
O00D H00Z 0.8508 . ?
O00D H 0.8506 . ?
C00E C00F 1.427(3) . ?
C00E C00J 1.378(3) . ?
C00F C00I 1.431(3) . ?
C00F C00V 1.459(4) . ?
C00G C00H 1.390(4) . ?
C00G C00J 1.400(3) . ?
C00H C00I 1.389(4) . ?
C00H C00S 1.510(3) . ?
C00J H00P 0.9300 . ?
C00K C00L 1.372(4) . ?
C00K C00N 1.436(3) . ?
C00L H00L 0.9300 . ?
C00L C00Q 1.397(4) . ?
C00M C00N 1.423(4) . ?
C00M C00P 1.392(4) . ?
C00N C00O 1.451(4) . ?
C00O C00U 1.498(4) . ?
C00P C00Q 1.399(4) . ?
C00P C00W 1.504(4) . ?
C00R H00Q 0.9700 . ?
C00R H00R 0.9700 . ?
C00R C00S 1.521(4) . ?
C00S H00S 0.9700 . ?
C00S H00T 0.9700 . ?
C00T H00D 0.9600 . ?
C00T H00E 0.9600 . ?
C00T H00F 0.9600 . ?
C00U H00G 0.9700 . ?
C00U H00H 0.9700 . ?
C00U H00I 0.9700 . ?
C00U H00J 0.9700 . ?
C00U C011 1.523(4) . ?
C00U C0 1.62(2) . ?
C00V C00Z 1.499(4) . ?
C00W H00K 0.9700 . ?
C00W H00M 0.9700 . ?
C00W C00X 1.509(4) . ?
C00X H00N 0.9700 . ?
C00X H00O 0.9700 . ?
C00Y H00U 0.9600 . ?
C00Y H00V 0.9600 . ?
C00Y H00W 0.9600 . ?
C00Z H00X 0.9700 . ?
C00Z H00Y 0.9700 . ?
C00Z C010 1.520(4) . ?
C010 H010 0.9800 . ?
C010 C012 1.499(4) . ?
C011 H011 0.9800 . ?
C011 C013 1.509(4) . ?
C012 H01D 0.9600 . ?
C012 H01E 0.9600 . ?
C012 H01F 0.9600 . ?
C013 H01A 0.9600 . ?
C013 H01B 0.9600 . ?
C013 H01C 0.9600 . ?
C0 H0 0.9800 . ?
C0 C1 1.60(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
C00E O001 C00Y 117.5(2) . . ?
C00I O002 H002 109.5 . . ?
C00K O003 C00T 117.8(2) . . ?
C00M O004 H004 109.5 . . ?
C00Q O005 H005 109.5 . . ?
C00R O007 H007 109.5 . . ?
C00G O008 H008 109.5 . . ?
C010 O009 H009 109.5 . . ?
C00X O00B H00B 109.5 . . ?
C011 O00C H00C 109.5 . . ?
C0 O00C H00A 109.5 . . ?
H00Z O00D H 109.4 . . ?
O001 C00E C00F 117.3(2) . . ?
O001 C00E C00J 121.6(2) . . ?
C00J C00E C00F 121.1(2) . . ?
C00E C00F C00I 116.3(2) . . ?
C00E C00F C00V 125.3(2) . . ?
C00I C00F C00V 118.4(2) . . ?
O008 C00G C00H 117.2(2) . . ?
O008 C00G C00J 120.5(2) . . ?
C00H C00G C00J 122.3(2) . . ?
C00G C00H C00S 121.4(2) . . ?
C00I C00H C00G 117.2(2) . . ?
C00I C00H C00S 121.3(2) . . ?
O002 C00I C00F 120.7(2) . . ?
O002 C00I C00H 116.0(2) . . ?
C00H C00I C00F 123.3(2) . . ?
C00E C00J C00G 119.8(2) . . ?
C00E C00J H00P 120.1 . . ?
C00G C00J H00P 120.1 . . ?
O003 C00K C00L 122.6(2) . . ?
O003 C00K C00N 116.6(2) . . ?
C00L C00K C00N 120.8(2) . . ?
C00K C00L H00L 119.7 . . ?
C00K C00L C00Q 120.7(2) . . ?
C00Q C00L H00L 119.7 . . ?
O004 C00M C00N 120.9(2) . . ?
O004 C00M C00P 115.9(2) . . ?
C00P C00M C00N 123.2(2) . . ?
C00K C00N C00O 124.6(2) . . ?
C00M C00N C00K 116.3(2) . . ?
C00M C00N C00O 119.1(2) . . ?
O006 C00O C00N 119.4(2) . . ?
O006 C00O C00U 116.8(2) . . ?
C00N C00O C00U 123.8(2) . . ?
C00M C00P C00Q 117.6(2) . . ?
C00M C00P C00W 120.2(2) . . ?
C00Q C00P C00W 122.1(2) . . ?
O005 C00Q C00L 121.7(2) . . ?
O005 C00Q C00P 117.0(2) . . ?
C00L C00Q C00P 121.3(2) . . ?
O007 C00R H00Q 108.9 . . ?
O007 C00R H00R 108.9 . . ?
O007 C00R C00S 113.3(2) . . ?
H00Q C00R H00R 107.7 . . ?
C00S C00R H00Q 108.9 . . ?
C00S C00R H00R 108.9 . . ?
C00H C00S C00R 110.0(2) . . ?
C00H C00S H00S 109.7 . . ?
C00H C00S H00T 109.7 . . ?
C00R C00S H00S 109.7 . . ?
C00R C00S H00T 109.7 . . ?
H00S C00S H00T 108.2 . . ?
O003 C00T H00D 109.5 . . ?
O003 C00T H00E 109.5 . . ?
O003 C00T H00F 109.5 . . ?
H00D C00T H00E 109.5 . . ?
H00D C00T H00F 109.5 . . ?
H00E C00T H00F 109.5 . . ?
C00O C00U H00G 109.4 . . ?
C00O C00U H00H 109.4 . . ?
C00O C00U H00I 106.5 . . ?
C00O C00U H00J 106.5 . . ?
C00O C00U C011 111.4(2) . . ?
C00O C00U C0 123.4(7) . . ?
H00G C00U H00H 108.0 . . ?
H00I C00U H00J 106.5 . . ?
C011 C00U H00G 109.4 . . ?
C011 C00U H00H 109.4 . . ?
C0 C00U H00I 106.5 . . ?
C0 C00U H00J 106.5 . . ?
O00A C00V C00F 120.3(2) . . ?
O00A C00V C00Z 116.6(2) . . ?
C00F C00V C00Z 123.2(2) . . ?
C00P C00W H00K 110.0 . . ?
C00P C00W H00M 110.0 . . ?
C00P C00W C00X 108.3(2) . . ?
H00K C00W H00M 108.4 . . ?
C00X C00W H00K 110.0 . . ?
C00X C00W H00M 110.0 . . ?
O00B C00X C00W 110.2(2) . . ?
O00B C00X H00N 109.6 . . ?
O00B C00X H00O 109.6 . . ?
C00W C00X H00N 109.6 . . ?
C00W C00X H00O 109.6 . . ?
H00N C00X H00O 108.1 . . ?
O001 C00Y H00U 109.5 . . ?
O001 C00Y H00V 109.5 . . ?
O001 C00Y H00W 109.5 . . ?
H00U C00Y H00V 109.5 . . ?
H00U C00Y H00W 109.5 . . ?
H00V C00Y H00W 109.5 . . ?
C00V C00Z H00X 108.9 . . ?
C00V C00Z H00Y 108.9 . . ?
C00V C00Z C010 113.4(2) . . ?
H00X C00Z H00Y 107.7 . . ?
C010 C00Z H00X 108.9 . . ?
C010 C00Z H00Y 108.9 . . ?
O009 C010 C00Z 111.5(2) . . ?
O009 C010 H010 108.4 . . ?
O009 C010 C012 108.2(3) . . ?
C00Z C010 H010 108.4 . . ?
C012 C010 C00Z 111.9(3) . . ?
C012 C010 H010 108.4 . . ?
O00C C011 C00U 109.5(3) . . ?
O00C C011 H011 109.5 . . ?
O00C C011 C013 108.0(3) . . ?
C00U C011 H011 109.5 . . ?
C013 C011 C00U 110.8(3) . . ?
C013 C011 H011 109.5 . . ?
C010 C012 H01D 109.5 . . ?
C010 C012 H01E 109.5 . . ?
C010 C012 H01F 109.5 . . ?
H01D C012 H01E 109.5 . . ?
H01D C012 H01F 109.5 . . ?
H01E C012 H01F 109.5 . . ?
C011 C013 H01A 109.5 . . ?
C011 C013 H01B 109.5 . . ?
C011 C013 H01C 109.5 . . ?
H01A C013 H01B 109.5 . . ?
H01A C013 H01C 109.5 . . ?
H01B C013 H01C 109.5 . . ?
O00C C0 C00U 113.1(15) . . ?
O00C C0 H0 117.6 . . ?
O00C C0 C1 85.1(15) . . ?
C00U C0 H0 117.6 . . ?
C1 C0 C00U 100.3(17) . . ?
C1 C0 H0 117.6 . . ?
C0 C1 H1A 109.5 . . ?
C0 C1 H1B 109.5 . . ?
C0 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_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 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.726
