# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_20180918_zy_pc_59-66
_database_code_depnum_ccdc_archive 'CCDC 1882029'
loop_
_audit_author_name
_audit_author_address
'yi zang'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2018-11-29 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_audit_creation_date             2018-09-20
_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         'C20 H18 O9, C H4 O'
_chemical_formula_sum            'C21 H22 O10'
_chemical_formula_weight         434.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   8.89350(10)
_cell_length_b                   14.43300(10)
_cell_length_c                   15.74510(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.0160(10)
_cell_angle_gamma                90
_cell_volume                     2019.79(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19089
_cell_measurement_temperature    286(5)
_cell_measurement_theta_max      73.5790
_cell_measurement_theta_min      2.7780
_shelx_estimated_absorpt_T_max   0.892
_shelx_estimated_absorpt_T_min   0.726
_exptl_absorpt_coefficient_mu    0.979
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26904
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.831
_diffrn_reflns_theta_min         4.156
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      286(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  10.00   0.50    0.50    --    0.00  36.00   6.00   52
  2  ω     27.00  81.00   0.50    0.50    --    0.00  36.00   6.00  108
  3  ω     77.00 124.00   0.50    0.50    --   94.60  36.00   6.00   94
  4  ω    134.00 160.00   0.50    0.50    --   94.60  36.00   6.00   52
  5  ω     29.00  62.00   0.50    0.50    --    0.00  38.00 150.00   66
  6  ω     20.00  88.00   0.50    0.50    --    0.00  19.00-180.00  136
  7  ω    -17.00  15.00   0.50    0.50    --    0.00  19.00-180.00   64
  8  ω    -31.00  31.00   0.50    0.50    --    0.00 -82.00 -60.00  124
  9  ω    -33.00  30.00   0.50    0.50    --    0.00 -82.00-180.00  126
 10  ω    -56.00 -28.00   0.50    0.50    --    0.00 -36.00-150.00   56
 11  ω    149.00 175.00   0.50    0.50    --   94.60  65.00  93.94   52
 12  ω     67.00  93.00   0.50    0.50    --   94.60  71.00 106.74   52
 13  ω     70.00 114.00   0.50    0.50    --   94.60  65.00  93.94   88
 14  ω     77.00 167.00   0.50    0.50    --   94.60  45.00-180.00  180
 15  ω    119.00 145.00   0.50    0.50    --   94.60  82.00-180.00   52
 16  ω    155.00 180.00   0.50    0.50    --   94.60  71.00 106.74   50
 17  ω     72.00  98.00   0.50    0.50    --   94.60  58.00 120.44   52
 18  ω     74.00 100.00   0.50    0.50    --   94.60  54.00  86.88   52
 19  ω     73.00 176.00   0.50    0.50    --   94.60  15.00 -30.00  206
 20  ω      5.00 110.00   0.50    0.50    --   94.60 -61.00  60.00  210
 21  ω     71.00  96.00   0.50    0.50    --   94.60  61.00  90.00   50
 22  ω     79.00 184.00   0.50    0.50    --   94.60  15.00 -90.00  210
 23  ω     75.00 102.00   0.50    0.50    --   94.60  45.00  60.00   54
 24  ω     69.00  95.00   0.50    0.50    --   94.60  72.00 111.51   52
 25  ω     75.00 174.00   0.50    0.50    --   94.60  45.00  90.00  198
 26  ω     75.00 101.00   0.50    0.50    --   94.60  45.00 133.01   52
 27  ω     71.00  97.00   0.50    0.50    --   94.60  61.00 150.00   52
 28  ω    148.00 174.00   0.50    0.50    --   94.60  82.00-180.00   52
 29  ω     80.00 119.00   0.50    0.50    --   94.60  30.00  90.00   78
 30  ω     71.00  97.00   0.50    0.50    --   94.60  61.00  60.00   52
 31  ω      7.00 109.00   0.50    0.50    --   94.60 -45.00  60.00  204
 32  ω     76.00 101.00   0.50    0.50    --   94.60 -36.00-150.00   50
 33  ω     78.00 161.00   0.50    0.50    --   94.60  30.00 150.00  166
 34  ω     86.00 111.00   0.50    0.50    --   94.60 -30.00  60.00   50
 35  ω     76.00 183.00   0.50    0.50    --   94.60  42.00 160.53  214
 36  ω     13.00  71.00   0.50    0.50    --   94.60 -36.00-150.00  116
;
_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      0.0831360000
_diffrn_orient_matrix_UB_12      0.0178896000
_diffrn_orient_matrix_UB_13      0.0859579000
_diffrn_orient_matrix_UB_21      -0.1297799000
_diffrn_orient_matrix_UB_22      -0.0462820000
_diffrn_orient_matrix_UB_23      0.0464895000
_diffrn_orient_matrix_UB_31      0.0792411000
_diffrn_orient_matrix_UB_32      -0.0944831000
_diffrn_orient_matrix_UB_33      -0.0064708000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3832
_reflns_number_total             4034
_reflns_odcompleteness_completeness 99.97
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4034
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0615P)²+0.4591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1134
_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 C(H,H,H,H,H,H) groups, All O(H) groups
2. Restrained distances
 O10-H10 = O11-H11
 0.85 with sigma of 0.02
 O10-C21 \\sim O11-C21
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O10) \\sim Ueq, Uanis(O11) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
4. Others
 Fixed Sof: O10(0.5) H21D(0.5) H21E(0.5) H21F(0.5) H21A(0.5) H21B(0.5)
 H21C(0.5) O11(0.5) H11(0.5) H10(0.5)
5.a Ternary CH refined with riding coordinates:
 C15(H15)
5.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C7(H7A,H7B)
5.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C20(H20A,H20B,H20C), C21(H21D,H21E,
 H21F), C21(H21A,H21B,H21C)
5.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O8(H8), O11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O4 O 0.20148(9) 0.59425(6) 0.25783(6) 0.0393(2) Uani 1 1 d . . . . .
O5 O 0.26534(9) 0.41518(6) 0.32635(6) 0.0358(2) Uani 1 1 d . . . . .
O3 O 0.25435(10) 0.47661(7) 0.16205(6) 0.0436(2) Uani 1 1 d . . . . .
O6 O 0.44779(10) 0.52635(6) 0.35596(6) 0.0412(2) Uani 1 1 d . . . . .
H6 H 0.5067 0.4949 0.3850 0.062 Uiso 1 1 calc GR . . . .
O9 O -0.05078(10) 0.67527(6) 0.28532(7) 0.0484(3) Uani 1 1 d . . . . .
O7 O 0.13368(12) 0.27324(7) 0.44299(7) 0.0552(3) Uani 1 1 d . . . . .
O8 O -0.35488(11) 0.40319(8) 0.42566(8) 0.0603(3) Uani 1 1 d . . . . .
H8 H -0.4050 0.3648 0.4506 0.090 Uiso 1 1 calc GR . . . .
O2 O 0.49259(11) 0.32252(6) 0.26351(7) 0.0500(3) Uani 1 1 d . . . . .
O1 O 0.80071(11) 0.50172(8) 0.13258(7) 0.0561(3) Uani 1 1 d . . . . .
C16 C -0.12786(16) 0.31171(11) 0.46620(11) 0.0535(4) Uani 1 1 d . . . . .
H16A H -0.1217 0.2892 0.5243 0.064 Uiso 1 1 calc R . . . .
H16B H -0.1822 0.2666 0.4313 0.064 Uiso 1 1 calc R . . . .
C12 C -0.03563(13) 0.59164(8) 0.32260(8) 0.0356(3) Uani 1 1 d . . . . .
C1 C 0.83139(17) 0.34585(12) 0.18720(11) 0.0570(4) Uani 1 1 d . . . . .
H1A H 0.8567 0.3218 0.1327 0.085 Uiso 1 1 calc GR . . . .
H1B H 0.7754 0.3002 0.2172 0.085 Uiso 1 1 calc GR . . . .
H1C H 0.9219 0.3606 0.2194 0.085 Uiso 1 1 calc GR . . . .
C10 C 0.1858(2) 0.51780(15) 0.08790(11) 0.0712(5) Uani 1 1 d . . . . .
H10A H 0.2623 0.5424 0.0528 0.107 Uiso 1 1 calc GR . . . .
H10B H 0.1201 0.5669 0.1044 0.107 Uiso 1 1 calc GR . . . .
H10C H 0.1287 0.4718 0.0567 0.107 Uiso 1 1 calc GR . . . .
C5 C 0.38050(13) 0.47156(8) 0.29291(8) 0.0326(3) Uani 1 1 d . . . . .
C7 C 0.43543(15) 0.60359(9) 0.19270(10) 0.0437(3) Uani 1 1 d . . . . .
H7A H 0.3983 0.6355 0.1420 0.052 Uiso 1 1 calc R . . . .
H7B H 0.4586 0.6496 0.2361 0.052 Uiso 1 1 calc R . . . .
C19 C 0.13397(12) 0.46050(8) 0.34092(7) 0.0317(2) Uani 1 1 d . . . . .
C3 C 0.60088(14) 0.45638(9) 0.20168(8) 0.0384(3) Uani 1 1 d . . . . .
C8 C 0.57531(15) 0.55005(9) 0.17340(9) 0.0422(3) Uani 1 1 d . . . . .
C9 C 0.69883(17) 0.57391(11) 0.13179(11) 0.0559(4) Uani 1 1 d . . . . .
H9 H 0.7136 0.6310 0.1061 0.067 Uiso 1 1 calc R . . . .
C6 C 0.31524(13) 0.53750(8) 0.22358(8) 0.0348(3) Uani 1 1 d . . . . .
C18 C 0.02619(13) 0.41741(8) 0.39068(7) 0.0331(3) Uani 1 1 d . . . . .
C14 C -0.10854(13) 0.46257(8) 0.40579(8) 0.0351(3) Uani 1 1 d . . . . .
C11 C 0.10183(13) 0.54682(8) 0.30662(8) 0.0331(2) Uani 1 1 d . . . . .
C13 C -0.14107(13) 0.54979(9) 0.37357(8) 0.0382(3) Uani 1 1 d . . . . .
H13 H -0.2306 0.5796 0.3856 0.046 Uiso 1 1 calc R . . . .
C15 C -0.20733(14) 0.40532(10) 0.46197(8) 0.0411(3) Uani 1 1 d . . . . .
H15 H -0.2086 0.4328 0.5189 0.049 Uiso 1 1 calc R . . . .
C20 C -0.18381(16) 0.72735(10) 0.30207(13) 0.0595(4) Uani 1 1 d . . . . .
H20A H -0.1852 0.7831 0.2688 0.089 Uiso 1 1 calc GR . . . .
H20B H -0.1842 0.7430 0.3613 0.089 Uiso 1 1 calc GR . . . .
H20C H -0.2711 0.6908 0.2873 0.089 Uiso 1 1 calc GR . . . .
C17 C 0.02875(14) 0.32709(9) 0.43317(8) 0.0396(3) Uani 1 1 d . . . . .
C4 C 0.49472(13) 0.40542(8) 0.25236(8) 0.0357(3) Uani 1 1 d . . . . .
C2 C 0.73926(15) 0.43042(10) 0.17549(9) 0.0439(3) Uani 1 1 d . . . . .
O10 O -0.5358(3) 0.2644(2) 0.46536(19) 0.0609(6) Uani 0.5 1 d D U P A 2
C21 C -0.5259(2) 0.22342(19) 0.54502(14) 0.0876(7) Uani 1 1 d D . . . .
H21D H -0.4671 0.1678 0.5423 0.131 Uiso 0.5 1 calc GR . P A 2
H21E H -0.6250 0.2086 0.5631 0.131 Uiso 0.5 1 calc GR . P A 2
H21F H -0.4786 0.2655 0.5849 0.131 Uiso 0.5 1 calc GR . P A 2
H21A H -0.4472 0.1953 0.5137 0.131 Uiso 0.5 1 calc GR . P A 1
H21B H -0.6106 0.1822 0.5460 0.131 Uiso 0.5 1 calc GR . P A 1
H21C H -0.4898 0.2355 0.6021 0.131 Uiso 0.5 1 calc GR . P A 1
O11 O -0.5702(3) 0.3080(3) 0.5054(2) 0.0785(8) Uani 0.5 1 d D U P A 1
H11 H -0.6487 0.3001 0.4775 0.118 Uiso 0.5 1 calc DGR . P A 1
H10 H -0.626(3) 0.279(3) 0.452(3) 0.079(16) Uiso 0.5 1 d D . 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
O4 C6 1.4227(14) . ?
O4 C11 1.3755(14) . ?
O5 C5 1.4235(14) . ?
O5 C19 1.3653(14) . ?
O3 C10 1.4277(18) . ?
O3 C6 1.4025(15) . ?
O6 H6 0.8200 . ?
O6 C5 1.3882(14) . ?
O9 C12 1.3469(15) . ?
O9 C20 1.4339(16) . ?
O7 C17 1.2201(16) . ?
O8 H8 0.8200 . ?
O8 C15 1.4132(16) . ?
O2 C4 1.2095(15) . ?
O1 C9 1.3805(19) . ?
O1 C2 1.3565(18) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.525(2) . ?
C16 C17 1.5202(19) . ?
C12 C11 1.4135(16) . ?
C12 C13 1.3933(17) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.478(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C5 C6 1.5459(16) . ?
C5 C4 1.5480(16) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.5045(17) . ?
C7 C6 1.5249(17) . ?
C19 C18 1.4044(16) . ?
C19 C11 1.3837(16) . ?
C3 C8 1.4389(18) . ?
C3 C4 1.4568(18) . ?
C3 C2 1.3641(18) . ?
C8 C9 1.3436(19) . ?
C9 H9 0.9300 . ?
C18 C14 1.3918(17) . ?
C18 C17 1.4650(16) . ?
C14 C13 1.3839(18) . ?
C14 C15 1.5139(17) . ?
C13 H13 0.9300 . ?
C15 H15 0.9800 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O10 C21 1.387(3) . ?
O10 H10 0.846(19) . ?
C21 H21D 0.9600 . ?
C21 H21E 0.9600 . ?
C21 H21F 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21 O11 1.421(4) . ?
O11 H11 0.8200 . ?

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
C11 O4 C6 113.95(9) . . ?
C19 O5 C5 114.80(9) . . ?
C6 O3 C10 116.58(12) . . ?
C5 O6 H6 109.5 . . ?
C12 O9 C20 117.39(11) . . ?
C15 O8 H8 109.5 . . ?
C2 O1 C9 107.54(11) . . ?
H16A C16 H16B 108.6 . . ?
C15 C16 H16A 110.4 . . ?
C15 C16 H16B 110.4 . . ?
C17 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
C17 C16 C15 106.53(11) . . ?
O9 C12 C11 113.99(11) . . ?
O9 C12 C13 125.49(11) . . ?
C13 C12 C11 120.52(11) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C5 C6 110.85(9) . . ?
O5 C5 C4 106.93(9) . . ?
O6 C5 O5 111.03(9) . . ?
O6 C5 C6 107.22(9) . . ?
O6 C5 C4 111.94(9) . . ?
C6 C5 C4 108.90(10) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C8 C7 C6 109.69(10) . . ?
C6 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
O5 C19 C18 119.11(10) . . ?
O5 C19 C11 122.14(10) . . ?
C11 C19 C18 118.73(10) . . ?
C8 C3 C4 123.05(11) . . ?
C2 C3 C8 107.40(12) . . ?
C2 C3 C4 129.48(12) . . ?
C3 C8 C7 122.88(11) . . ?
C9 C8 C7 131.52(13) . . ?
C9 C8 C3 105.58(12) . . ?
O1 C9 H9 124.8 . . ?
C8 C9 O1 110.47(13) . . ?
C8 C9 H9 124.8 . . ?
O4 C6 C5 109.95(10) . . ?
O4 C6 C7 106.05(9) . . ?
O3 C6 O4 111.11(9) . . ?
O3 C6 C5 103.20(9) . . ?
O3 C6 C7 115.45(11) . . ?
C7 C6 C5 111.12(10) . . ?
C19 C18 C17 130.45(11) . . ?
C14 C18 C19 119.77(11) . . ?
C14 C18 C17 109.78(11) . . ?
C18 C14 C15 111.41(11) . . ?
C13 C14 C18 122.24(11) . . ?
C13 C14 C15 126.34(11) . . ?
O4 C11 C12 116.73(10) . . ?
O4 C11 C19 122.53(10) . . ?
C19 C11 C12 120.71(11) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 C12 117.99(11) . . ?
C14 C13 H13 121.0 . . ?
O8 C15 C16 114.88(12) . . ?
O8 C15 C14 108.97(10) . . ?
O8 C15 H15 109.8 . . ?
C16 C15 H15 109.8 . . ?
C14 C15 C16 103.39(10) . . ?
C14 C15 H15 109.8 . . ?
O9 C20 H20A 109.5 . . ?
O9 C20 H20B 109.5 . . ?
O9 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O7 C17 C16 124.72(12) . . ?
O7 C17 C18 128.63(12) . . ?
C18 C17 C16 106.64(10) . . ?
O2 C4 C5 122.43(11) . . ?
O2 C4 C3 126.35(11) . . ?
C3 C4 C5 111.22(10) . . ?
O1 C2 C1 117.22(12) . . ?
O1 C2 C3 109.01(12) . . ?
C3 C2 C1 133.73(14) . . ?
C21 O10 H10 111(3) . . ?
O10 C21 H21D 109.5 . . ?
O10 C21 H21E 109.5 . . ?
O10 C21 H21F 109.5 . . ?
H21D C21 H21E 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O11 C21 H21A 109.5 . . ?
O11 C21 H21B 109.5 . . ?
O11 C21 H21C 109.5 . . ?
C21 O11 H11 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 C5 C6 O4 58.19(12) . . . . ?
O5 C5 C6 O3 -60.40(11) . . . . ?
O5 C5 C6 C7 175.28(9) . . . . ?
O5 C5 C4 O2 -11.79(16) . . . . ?
O5 C5 C4 C3 168.68(10) . . . . ?
O5 C19 C18 C14 -179.73(10) . . . . ?
O5 C19 C18 C17 0.42(19) . . . . ?
O5 C19 C11 O4 -2.11(18) . . . . ?
O5 C19 C11 C12 179.66(10) . . . . ?
O6 C5 C6 O4 -63.14(12) . . . . ?
O6 C5 C6 O3 178.26(9) . . . . ?
O6 C5 C6 C7 53.95(13) . . . . ?
O6 C5 C4 O2 110.01(14) . . . . ?
O6 C5 C4 C3 -69.52(13) . . . . ?
O9 C12 C11 O4 1.43(16) . . . . ?
O9 C12 C11 C19 179.76(11) . . . . ?
O9 C12 C13 C14 178.90(12) . . . . ?
C10 O3 C6 O4 62.91(15) . . . . ?
C10 O3 C6 C5 -179.31(12) . . . . ?
C10 O3 C6 C7 -57.88(15) . . . . ?
C5 O5 C19 C18 -165.99(10) . . . . ?
C5 O5 C19 C11 15.51(16) . . . . ?
C7 C8 C9 O1 178.00(14) . . . . ?
C19 O5 C5 O6 76.79(12) . . . . ?
C19 O5 C5 C6 -42.27(13) . . . . ?
C19 O5 C5 C4 -160.84(9) . . . . ?
C19 C18 C14 C13 -0.27(18) . . . . ?
C19 C18 C14 C15 -178.90(10) . . . . ?
C19 C18 C17 O7 9.6(2) . . . . ?
C19 C18 C17 C16 -171.63(13) . . . . ?
C3 C8 C9 O1 -0.44(18) . . . . ?
C8 C7 C6 O4 167.47(11) . . . . ?
C8 C7 C6 O3 -69.04(14) . . . . ?
C8 C7 C6 C5 48.02(15) . . . . ?
C8 C3 C4 O2 163.69(14) . . . . ?
C8 C3 C4 C5 -16.80(17) . . . . ?
C8 C3 C2 O1 -0.24(15) . . . . ?
C8 C3 C2 C1 177.11(15) . . . . ?
C9 O1 C2 C1 -177.87(13) . . . . ?
C9 O1 C2 C3 -0.03(16) . . . . ?
C6 O4 C11 C12 -162.74(11) . . . . ?
C6 O4 C11 C19 18.96(16) . . . . ?
C6 C5 C4 O2 -131.62(13) . . . . ?
C6 C5 C4 C3 48.85(13) . . . . ?
C6 C7 C8 C3 -14.85(19) . . . . ?
C6 C7 C8 C9 166.94(16) . . . . ?
C18 C19 C11 O4 179.39(10) . . . . ?
C18 C19 C11 C12 1.16(18) . . . . ?
C18 C14 C13 C12 1.70(19) . . . . ?
C18 C14 C15 O8 -132.50(12) . . . . ?
C18 C14 C15 C16 -9.87(14) . . . . ?
C14 C18 C17 O7 -170.30(14) . . . . ?
C14 C18 C17 C16 8.50(15) . . . . ?
C11 O4 C6 O3 68.47(13) . . . . ?
C11 O4 C6 C5 -45.14(13) . . . . ?
C11 O4 C6 C7 -165.35(10) . . . . ?
C11 C12 C13 C14 -1.71(19) . . . . ?
C11 C19 C18 C14 -1.18(17) . . . . ?
C11 C19 C18 C17 178.97(12) . . . . ?
C13 C12 C11 O4 -178.03(11) . . . . ?
C13 C12 C11 C19 0.30(19) . . . . ?
C13 C14 C15 O8 48.93(18) . . . . ?
C13 C14 C15 C16 171.56(13) . . . . ?
C15 C16 C17 O7 164.41(14) . . . . ?
C15 C16 C17 C18 -14.45(15) . . . . ?
C15 C14 C13 C12 -179.87(12) . . . . ?
C20 O9 C12 C11 -176.83(13) . . . . ?
C20 O9 C12 C13 2.6(2) . . . . ?
C17 C16 C15 O8 133.08(13) . . . . ?
C17 C16 C15 C14 14.47(15) . . . . ?
C17 C18 C14 C13 179.62(11) . . . . ?
C17 C18 C14 C15 0.98(14) . . . . ?
C4 C5 C6 O4 175.56(9) . . . . ?
C4 C5 C6 O3 56.97(11) . . . . ?
C4 C5 C6 C7 -67.35(13) . . . . ?
C4 C3 C8 C7 -0.8(2) . . . . ?
C4 C3 C8 C9 177.82(13) . . . . ?
C4 C3 C2 O1 -177.42(12) . . . . ?
C4 C3 C2 C1 -0.1(3) . . . . ?
C2 O1 C9 C8 0.30(18) . . . . ?
C2 C3 C8 C7 -178.20(13) . . . . ?
C2 C3 C8 C9 0.41(16) . . . . ?
C2 C3 C4 O2 -19.5(2) . . . . ?
C2 C3 C4 C5 159.99(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 1.506
_oxdiff_exptl_absorpt_empirical_full_min 0.722
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_chemical_compound_source        fungus
####################################################################### 
# 
# 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_20181102_zy_pc_35
_database_code_depnum_ccdc_archive 'CCDC 1882030'
loop_
_audit_author_name
_audit_author_address
'yi zang'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2018-11-29 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_audit_creation_date             2018-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 O9, H2 O'
_chemical_formula_sum            'C20 H20 O10'
_chemical_formula_weight         420.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.0160(2)
_cell_length_b                   9.3778(2)
_cell_length_c                   10.6360(2)
_cell_angle_alpha                93.717(2)
_cell_angle_beta                 90.826(2)
_cell_angle_gamma                92.317(2)
_cell_volume                     896.52(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10882
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.5380
_cell_measurement_theta_min      4.1660
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.813
_exptl_absorpt_coefficient_mu    1.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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_primary    colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18581
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.821
_diffrn_reflns_theta_min         4.166
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  26.00   0.50    0.50    --    0.00  38.00-180.00   52
  2  ω    -16.00  34.00   0.50    0.50    --    0.00  38.00 150.00  100
  3  ω    -21.00  54.00   0.50    0.50    --    0.00  57.00  60.00  150
  4  ω    -15.00  89.00   0.50    0.50    --    0.00  38.00 -30.00  208
  5  ω    -21.00  13.00   0.50    0.50    --    0.00  57.00-120.00   68
  6  ω     21.00  81.00   0.50    0.50    --    0.00  57.00-120.00  120
  7  ω     52.00  88.00   0.50    0.50    --    0.00  38.00-180.00   72
  8  ω     41.00  79.00   0.50    0.50    --    0.00  38.00 150.00   76
  9  ω     67.00  95.00   0.50    1.50    --   94.60  73.00  81.03   56
 10  ω    139.00 178.00   0.50    1.50    --   94.60  69.00-175.89   78
 11  ω    142.00 168.00   0.50    1.50    --   94.60  61.00 126.14   52
 12  ω     72.00 107.00   0.50    1.50    --   94.60  61.00 158.57   70
 13  ω     67.00  94.00   0.50    1.50    --   94.60  72.00-132.97   54
 14  ω    140.00 167.00   0.50    1.50    --   94.60  72.00-132.97   54
 15  ω    147.00 178.00   0.50    1.50    --   94.60  75.00 -90.47   62
 16  ω     68.00  96.00   0.50    1.50    --   94.60  69.00-175.89   56
 17  ω    152.00 178.00   0.50    1.50    --   94.60  70.00 161.12   52
 18  ω     73.00 176.00   0.50    1.50    --   94.60  52.00 -86.18  206
 19  ω     71.00 113.00   0.50    1.50    --   94.60  61.00 126.14   84
 20  ω     79.00 178.00   0.50    1.50    --   94.60  30.00-180.00  198
 21  ω     69.00  95.00   0.50    1.50    --   94.60  70.00 161.12   52
 22  ω     74.00 123.00   0.50    1.50    --   94.60  61.00-180.00   98
 23  ω     72.00  98.00   0.50    1.50    --   94.60  61.00  60.00   52
 24  ω     61.00  87.00   0.50    1.50    --   94.60 -82.00-180.00   52
 25  ω     82.00 149.00   0.50    1.50    --   94.60  45.00-120.00  134
 26  ω    154.00 183.00   0.50    1.50    --   94.60  45.00-120.00   58
 27  ω     12.00  62.00   0.50    1.50    --   94.60 -82.00 -30.00  100
 28  ω     65.00 126.00   0.50    1.50    --   94.60 -82.00 -30.00  122
 29  ω     72.00  97.00   0.50    1.50    --   94.60  61.00   4.08   50
 30  ω     71.00 166.00   0.50    1.50    --   94.60  61.00 -30.00  190
 31  ω     69.00 184.00   0.50    1.50    --   94.60  66.00 -52.22  230
 32  ω     71.00  97.00   0.50    1.50    --   94.60  61.00-150.00   52
 33  ω     78.00 171.00   0.50    1.50    --   94.60  45.00  90.00  186
 34  ω    155.00 180.00   0.50    1.50    --   94.60  70.00 104.83   50
 35  ω     72.00  98.00   0.50    1.50    --   94.60  61.00 -90.00   52
 36  ω     72.00  98.00   0.50    1.50    --   94.60  61.00 -60.00   52
 37  ω     72.00 135.00   0.50    1.50    --   94.60  61.00  30.00  126
 38  ω     72.00  98.00   0.50    1.50    --   94.60  61.00  90.00   52
 39  ω      6.00 124.00   0.50    1.50    --   94.60 -82.00 -60.00  236
 40  ω      6.00 126.00   0.50    1.50    --   94.60 -82.00 120.00  240
 41  ω     68.00 111.00   0.50    1.50    --   94.60  70.00 104.83   86
 42  ω     75.00 127.00   0.50    1.50    --   94.60  45.00 -90.00  104
 43  ω    133.00 158.00   0.50    1.50    --   94.60  73.00  81.03   50
 44  ω     69.00  94.00   0.50    1.50    --   94.60  68.00   9.90   50
 45  ω     66.00  92.00   0.50    1.50    --   94.60  75.00 -90.47   52
 46  ω     71.00  97.00   0.50    1.50    --   94.60  61.00 150.00   52
 47  ω     70.00 179.00   0.50    1.50    --   94.60  64.00  38.38  218
 48  ω     29.00 122.00   0.50    1.50    --   94.60 -82.00-150.00  186
 49  ω      9.00  78.00   0.50    1.50    --   94.60 -82.00  30.00  138
 50  ω     85.00 122.00   0.50    1.50    --   94.60 -82.00  30.00   74
 51  ω     74.00 182.00   0.50    1.50    --   94.60  49.00  11.19  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      0.0238021000
_diffrn_orient_matrix_UB_12      0.0363309000
_diffrn_orient_matrix_UB_13      0.1423837000
_diffrn_orient_matrix_UB_21      -0.0075134000
_diffrn_orient_matrix_UB_22      0.1604622000
_diffrn_orient_matrix_UB_23      -0.0214517000
_diffrn_orient_matrix_UB_31      -0.1692031000
_diffrn_orient_matrix_UB_32      -0.0089195000
_diffrn_orient_matrix_UB_33      0.0184745000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3256
_reflns_number_total             3560
_reflns_odcompleteness_completeness 99.69
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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         0.243
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3560
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.050
_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)+(0.0355P)²+0.4720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0840
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O008-H008
 0.82 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00B), C00T(H00J,H00K)
3.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00Q(H00Q)
3.c Idealised Me refined as rotating group:
 C00R(H00C,H00D,H00E), C00S(H00F,H00H,H00I), C00U(H00L,H00N,H00O)
3.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_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 0.36499(10) 0.74545(9) 0.17690(8) 0.01667(19) Uani 1 1 d . . . . .
O002 O 0.63477(10) 0.78119(9) 0.09628(9) 0.0187(2) Uani 1 1 d . . . . .
O003 O 0.09008(10) 0.58645(9) 0.11408(8) 0.0174(2) Uani 1 1 d . . . . .
H003 H 0.137187 0.638300 0.068432 0.026 Uiso 1 1 calc GR . . . .
O004 O 0.30387(10) 0.71735(9) 0.38720(8) 0.0178(2) Uani 1 1 d . . . . .
O005 O -0.20468(10) 0.85825(10) 0.42431(9) 0.0202(2) Uani 1 1 d . . . . .
O006 O -0.00698(10) 0.45022(9) 0.35726(8) 0.0193(2) Uani 1 1 d . . . . .
O007 O 0.25444(9) 0.47197(9) 0.23977(8) 0.01621(19) Uani 1 1 d . . . . .
O008 O 0.83331(10) 0.24677(10) 0.07465(9) 0.0195(2) Uani 1 1 d D . . . .
O009 O 0.35384(10) 0.16613(10) 0.24990(9) 0.0222(2) Uani 1 1 d . . . . .
O00A O 0.05040(11) 0.19471(10) 0.23944(9) 0.0216(2) Uani 1 1 d . . . . .
C00B C 0.39743(14) 0.49430(13) 0.20145(11) 0.0151(2) Uani 1 1 d . . . . .
C00C C 0.59898(14) 0.64712(13) 0.12894(11) 0.0156(3) Uani 1 1 d . . . . .
C00D C 0.49260(14) 0.37898(13) 0.19310(11) 0.0156(3) Uani 1 1 d . . . . .
C00E C 0.03060(14) 0.56819(13) 0.32365(11) 0.0157(3) Uani 1 1 d . . . . .
C00F C 0.45217(14) 0.62745(13) 0.17045(11) 0.0155(3) Uani 1 1 d . . . . .
C00G C 0.69538(14) 0.53409(13) 0.12501(11) 0.0165(3) Uani 1 1 d . . . . .
H00G H 0.793410 0.546977 0.100661 0.020 Uiso 1 1 calc R . . . .
C00H C -0.04409(14) 0.69916(13) 0.35600(11) 0.0164(3) Uani 1 1 d . . . . .
C00I C 0.01201(14) 0.83870(13) 0.32521(12) 0.0173(3) Uani 1 1 d . . . . .
C00J C 0.46506(14) 0.22613(13) 0.21034(12) 0.0168(3) Uani 1 1 d . . . . .
C00K C 0.15952(14) 0.58991(13) 0.23150(11) 0.0151(3) Uani 1 1 d . . . . .
C00L C 0.64019(14) 0.40228(13) 0.15855(11) 0.0157(3) Uani 1 1 d . . . . .
C00M C 0.72552(14) 0.26790(14) 0.17039(12) 0.0171(3) Uani 1 1 d . . . . .
C00N C -0.17619(15) 0.71686(13) 0.41572(12) 0.0175(3) Uani 1 1 d . . . . .
C00O C 0.15218(14) 0.86085(13) 0.25322(12) 0.0173(3) Uani 1 1 d . . . . .
H00A H 0.205830 0.947101 0.286685 0.021 Uiso 1 1 calc R . . . .
H00B H 0.128374 0.871685 0.165208 0.021 Uiso 1 1 calc R . . . .
C00P C 0.24783(14) 0.73220(13) 0.26513(11) 0.0158(3) Uani 1 1 d . . . . .
C00Q C -0.08816(15) 0.93101(14) 0.36896(12) 0.0196(3) Uani 1 1 d . . . . .
H00Q H -0.080553 1.029535 0.363023 0.024 Uiso 1 1 calc R . . . .
C00R C 0.77965(14) 0.80483(14) 0.04531(13) 0.0206(3) Uani 1 1 d . . . . .
H00C H 0.792995 0.737535 -0.025141 0.031 Uiso 1 1 calc GR . . . .
H00D H 0.853795 0.792403 0.108910 0.031 Uiso 1 1 calc GR . . . .
H00E H 0.789006 0.900345 0.018075 0.031 Uiso 1 1 calc GR . . . .
C00S C -0.28904(15) 0.61682(14) 0.46472(12) 0.0202(3) Uani 1 1 d . . . . .
H00F H -0.311802 0.647677 0.549840 0.030 Uiso 1 1 calc GR . . . .
H00H H -0.251073 0.522551 0.462900 0.030 Uiso 1 1 calc GR . . . .
H00I H -0.377489 0.615327 0.413225 0.030 Uiso 1 1 calc GR . . . .
C00T C 0.60301(14) 0.14993(14) 0.16841(13) 0.0201(3) Uani 1 1 d . . . . .
H00J H 0.588796 0.104557 0.084290 0.024 Uiso 1 1 calc R . . . .
H00K H 0.627234 0.077707 0.225814 0.024 Uiso 1 1 calc R . . . .
C00U C 0.38883(16) 0.83885(15) 0.44259(13) 0.0245(3) Uani 1 1 d . . . . .
H00L H 0.461515 0.869526 0.383909 0.037 Uiso 1 1 calc GR . . . .
H00N H 0.437939 0.812960 0.517977 0.037 Uiso 1 1 calc GR . . . .
H00O H 0.323840 0.915300 0.462918 0.037 Uiso 1 1 calc GR . . . .
H00M H 0.7780(17) 0.2759(16) 0.2549(14) 0.017(4) Uiso 1 1 d . . . . .
H00P H 0.149(3) 0.185(2) 0.236(2) 0.052(6) Uiso 1 1 d . . . . .
H00R H 0.039(3) 0.282(3) 0.279(2) 0.066(7) Uiso 1 1 d . . . . .
H008 H 0.9106(16) 0.227(2) 0.1120(18) 0.049(6) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00F 1.3817(15) . ?
O001 C00P 1.4300(15) . ?
O002 C00C 1.3538(15) . ?
O002 C00R 1.4359(15) . ?
O003 H003 0.8200 . ?
O003 C00K 1.3869(14) . ?
O004 C00P 1.4038(15) . ?
O004 C00U 1.4357(16) . ?
O005 C00N 1.3583(15) . ?
O005 C00Q 1.3885(16) . ?
O006 C00E 1.2210(15) . ?
O007 C00B 1.3698(15) . ?
O007 C00K 1.4319(14) . ?
O008 C00M 1.4278(15) . ?
O008 H008 0.831(10) . ?
O009 C00J 1.2232(16) . ?
O00A H00P 0.90(2) . ?
O00A H00R 0.91(3) . ?
C00B C00D 1.4067(17) . ?
C00B C00F 1.3855(17) . ?
C00C C00F 1.4102(18) . ?
C00C C00G 1.3966(17) . ?
C00D C00J 1.4685(17) . ?
C00D C00L 1.3980(18) . ?
C00E C00H 1.4488(17) . ?
C00E C00K 1.5469(17) . ?
C00G H00G 0.9300 . ?
C00G C00L 1.3840(18) . ?
C00H C00I 1.4430(17) . ?
C00H C00N 1.3688(18) . ?
C00I C00O 1.5013(17) . ?
C00I C00Q 1.3434(18) . ?
C00J C00T 1.5175(18) . ?
C00K C00P 1.5448(17) . ?
C00L C00M 1.5139(17) . ?
C00M C00T 1.5303(18) . ?
C00M H00M 1.007(15) . ?
C00N C00S 1.4793(18) . ?
C00O H00A 0.9700 . ?
C00O H00B 0.9700 . ?
C00O C00P 1.5219(17) . ?
C00Q H00Q 0.9300 . ?
C00R H00C 0.9600 . ?
C00R H00D 0.9600 . ?
C00R H00E 0.9600 . ?
C00S H00F 0.9600 . ?
C00S H00H 0.9600 . ?
C00S H00I 0.9600 . ?
C00T H00J 0.9700 . ?
C00T H00K 0.9700 . ?
C00U H00L 0.9600 . ?
C00U H00N 0.9600 . ?
C00U H00O 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 C00P 112.17(9) . . ?
C00C O002 C00R 116.83(10) . . ?
C00K O003 H003 109.5 . . ?
C00P O004 C00U 115.42(10) . . ?
C00N O005 C00Q 107.75(10) . . ?
C00B O007 C00K 115.98(9) . . ?
C00M O008 H008 105.6(15) . . ?
H00P O00A H00R 105(2) . . ?
O007 C00B C00D 119.35(11) . . ?
O007 C00B C00F 122.13(11) . . ?
C00F C00B C00D 118.52(11) . . ?
O002 C00C C00F 114.49(11) . . ?
O002 C00C C00G 124.98(11) . . ?
C00G C00C C00F 120.52(11) . . ?
C00B C00D C00J 131.24(11) . . ?
C00L C00D C00B 119.57(11) . . ?
C00L C00D C00J 109.15(11) . . ?
O006 C00E C00H 125.19(12) . . ?
O006 C00E C00K 121.99(11) . . ?
C00H C00E C00K 112.67(10) . . ?
O001 C00F C00B 121.58(11) . . ?
O001 C00F C00C 117.36(11) . . ?
C00B C00F C00C 121.05(11) . . ?
C00C C00G H00G 121.1 . . ?
C00L C00G C00C 117.80(12) . . ?
C00L C00G H00G 121.1 . . ?
C00I C00H C00E 123.55(11) . . ?
C00N C00H C00E 128.92(12) . . ?
C00N C00H C00I 107.51(11) . . ?
C00H C00I C00O 122.74(11) . . ?
C00Q C00I C00H 105.71(12) . . ?
C00Q C00I C00O 131.49(12) . . ?
O009 C00J C00D 128.52(12) . . ?
O009 C00J C00T 124.23(11) . . ?
C00D C00J C00T 107.24(11) . . ?
O003 C00K O007 110.94(9) . . ?
O003 C00K C00E 104.11(10) . . ?
O003 C00K C00P 112.72(10) . . ?
O007 C00K C00E 107.53(9) . . ?
O007 C00K C00P 110.12(10) . . ?
C00P C00K C00E 111.17(10) . . ?
C00D C00L C00M 110.26(11) . . ?
C00G C00L C00D 122.39(12) . . ?
C00G C00L C00M 127.28(11) . . ?
O008 C00M C00L 113.23(10) . . ?
O008 C00M C00T 113.96(10) . . ?
O008 C00M H00M 108.6(9) . . ?
C00L C00M C00T 103.21(10) . . ?
C00L C00M H00M 107.8(9) . . ?
C00T C00M H00M 109.7(9) . . ?
O005 C00N C00H 108.76(11) . . ?
O005 C00N C00S 117.44(11) . . ?
C00H C00N C00S 133.75(12) . . ?
C00I C00O H00A 109.9 . . ?
C00I C00O H00B 109.9 . . ?
C00I C00O C00P 108.96(10) . . ?
H00A C00O H00B 108.3 . . ?
C00P C00O H00A 109.9 . . ?
C00P C00O H00B 109.9 . . ?
O001 C00P C00K 108.30(10) . . ?
O001 C00P C00O 106.68(10) . . ?
O004 C00P O001 111.34(10) . . ?
O004 C00P C00K 104.19(10) . . ?
O004 C00P C00O 114.42(10) . . ?
C00O C00P C00K 111.84(10) . . ?
O005 C00Q H00Q 124.9 . . ?
C00I C00Q O005 110.27(11) . . ?
C00I C00Q H00Q 124.9 . . ?
O002 C00R H00C 109.5 . . ?
O002 C00R H00D 109.5 . . ?
O002 C00R H00E 109.5 . . ?
H00C C00R H00D 109.5 . . ?
H00C C00R H00E 109.5 . . ?
H00D C00R H00E 109.5 . . ?
C00N C00S H00F 109.5 . . ?
C00N C00S H00H 109.5 . . ?
C00N C00S H00I 109.5 . . ?
H00F C00S H00H 109.5 . . ?
H00F C00S H00I 109.5 . . ?
H00H C00S H00I 109.5 . . ?
C00J C00T C00M 104.71(10) . . ?
C00J C00T H00J 110.8 . . ?
C00J C00T H00K 110.8 . . ?
C00M C00T H00J 110.8 . . ?
C00M C00T H00K 110.8 . . ?
H00J C00T H00K 108.9 . . ?
O004 C00U H00L 109.5 . . ?
O004 C00U H00N 109.5 . . ?
O004 C00U H00O 109.5 . . ?
H00L C00U H00N 109.5 . . ?
H00L C00U H00O 109.5 . . ?
H00N C00U H00O 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O003 H003 O008 0.82 1.94 2.7041(13) 155.5 2_665 yes
O00A H00P O009 0.90(2) 1.87(2) 2.7610(14) 173(2) . yes
O00A H00R O006 0.91(3) 1.80(3) 2.7035(13) 173(2) . yes
O008 H008 O00A 0.831(10) 1.885(11) 2.6890(13) 163(2) 1_655 yes

_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 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.830
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_chemical_compound_source        fungus
####################################################################### 
# 
# 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_20181128_zy-pc-46-55
_database_code_depnum_ccdc_archive 'CCDC 1885788'
loop_
_audit_author_name
_audit_author_address
'yi zang'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2018-12-18 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_audit_creation_date             2018-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 O10, C H4 O'
_chemical_formula_sum            'C21 H22 O11'
_chemical_formula_weight         450.38
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   8.33914(3)
_cell_length_b                   13.29606(5)
_cell_length_c                   18.06836(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2003.377(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    36688
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6720
_cell_measurement_theta_min      3.3210
_shelx_estimated_absorpt_T_max   0.902
_shelx_estimated_absorpt_T_min   0.780
_exptl_absorpt_coefficient_mu    1.047
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            45175
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.971
_diffrn_reflns_theta_min         3.324
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  13.00   0.50    0.50    --    0.00  29.00  61.00   54
  2  ω     23.00  59.00   0.50    0.50    --   94.60 -29.00 -99.00   72
  3  ω    141.00 168.00   0.50    0.50    --   94.60  29.00  61.00   54
  4  ω     78.00 134.00   0.50    0.50    --   94.60  29.00  61.00  112
  5  ω      5.00  41.00   0.50    0.50    --    0.00  57.00 -90.00   72
  6  ω     44.00  70.00   0.50    0.50    --    0.00  38.00-150.00   52
  7  ω    -30.00  22.00   0.50    0.50    --    0.00 -82.00-180.00  104
  8  ω     25.00  50.00   0.50    0.50    --    0.00  29.00  61.00   50
  9  ω    -29.00  31.00   0.50    0.50    --    0.00 -82.00 120.00  120
 10  ω     44.00  88.00   0.50    0.50    --    0.00  57.00 -90.00   88
 11  ω    -15.00  40.00   0.50    0.50    --    0.00  38.00-150.00  110
 12  ω    -17.00  69.00   0.50    0.50    --    0.00  38.00 -90.00  172
 13  ω    -22.00  22.00   0.50    0.50    --    0.00  57.00 -30.00   88
 14  ω    -61.00 -36.00   0.50    0.50    --    0.00 -29.00 -99.00   50
 15  ω     31.00  83.00   0.50    0.50    --    0.00  57.00 -30.00  104
 16  ω    -17.00  80.00   0.50    0.50    --    0.00  38.00 120.00  194
 17  ω     66.00  92.00   0.50    0.50    --   94.60  75.00  81.38   52
 18  ω     67.00  93.00   0.50    0.50    --   94.60  72.00 -82.76   52
 19  ω    107.00 132.00   0.50    0.50    --   94.60  45.00 -30.00   50
 20  ω    111.00 137.00   0.50    0.50    --   94.60  61.00   8.36   52
 21  ω     72.00 108.00   0.50    0.50    --   94.60  61.00   8.36   72
 22  ω     75.00 100.00   0.50    0.50    --   94.60  45.00 -30.00   50
 23  ω     66.00 184.00   0.50    0.50    --   94.60  75.00 -97.79  236
 24  ω     67.00  93.00   0.50    0.50    --   94.60  72.00  61.40   52
 25  ω     71.00  97.00   0.50    0.50    --   94.60  61.00 -30.00   52
 26  ω     66.00  95.00   0.50    0.50    --   94.60  75.00-154.41   58
 27  ω     67.00 183.00   0.50    0.50    --   94.60  71.00-133.83  232
 28  ω      6.00 126.00   0.50    0.50    --   94.60 -82.00 -30.00  240
 29  ω     71.00  96.00   0.50    0.50    --   94.60  60.00  51.29   50
 30  ω    142.00 167.00   0.50    0.50    --   94.60  60.00  51.29   50
 31  ω     73.00 127.00   0.50    0.50    --   94.60  61.00 113.35  108
 32  ω     71.00 102.00   0.50    0.50    --   94.60  61.00-180.00   62
 33  ω     71.00 152.00   0.50    0.50    --   94.60  61.00-150.00  162
 34  ω     46.00  74.00   0.50    0.50    --   94.60 -82.00-150.00   56
 35  ω     71.00  97.00   0.50    0.50    --   94.60  63.00-105.77   52
 36  ω    138.00 174.00   0.50    0.50    --   94.60  61.00  30.00   72
 37  ω    137.00 183.00   0.50    0.50    --   94.60  75.00 107.78   92
 38  ω    148.00 174.00   0.50    0.50    --   94.60  72.00-175.15   52
 39  ω     71.00  99.00   0.50    0.50    --   94.60  61.00   0.00   56
 40  ω     71.00  97.00   0.50    0.50    --   94.60  61.00  30.00   52
 41  ω     71.00  97.00   0.50    0.50    --   94.60  61.00 -90.00   52
 42  ω     71.00 154.00   0.50    0.50    --   94.60  61.00  90.00  166
 43  ω     67.00  92.00   0.50    0.50    --   94.60  71.00 -25.73   50
 44  ω     67.00 150.00   0.50    0.50    --   94.60  71.00 137.73  166
 45  ω    158.00 184.00   0.50    0.50    --   94.60  71.00 137.73   52
 46  ω     67.00  93.00   0.50    0.50    --   94.60  71.00 -36.30   52
 47  ω     99.00 183.00   0.50    0.50    --   94.60  71.00 -36.30  168
 48  ω     68.00  94.00   0.50    0.50    --   94.60  74.00  89.84   52
 49  ω     66.00  92.00   0.50    0.50    --   94.60  75.00 107.78   52
 50  ω     67.00 147.00   0.50    0.50    --   94.60  71.00 152.18  160
 51  ω    107.00 172.00   0.50    0.50    --   94.60  71.00 -73.78  130
 52  ω     67.00 100.00   0.50    0.50    --   94.60  71.00 -73.78   66
 53  ω      6.00  75.00   0.50    0.50    --   94.60 -77.00-120.00  138
 54  ω     88.00 123.00   0.50    0.50    --   94.60 -77.00-120.00   70
 55  ω     70.00 144.00   0.50    0.50    --   94.60  64.00-171.76  148
 56  ω     79.00 112.00   0.50    0.50    --   94.60 -82.00-150.00   66
 57  ω     13.00 120.00   0.50    0.50    --   94.60 -82.00  90.00  214
 58  ω     71.00 183.00   0.50    0.50    --   94.60  61.00  60.00  224
 59  ω     20.00  72.00   0.50    0.50    --   94.60 -82.00  30.00  104
 60  ω     93.00 125.00   0.50    0.50    --   94.60 -82.00  30.00   64
 61  ω     68.00  94.00   0.50    0.50    --   94.60  70.00 124.55   52
 62  ω      6.00 123.00   0.50    0.50    --   94.60 -82.00-180.00  234
 63  ω     67.00  93.00   0.50    0.50    --   94.60  72.00-175.15   52
;
_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      -0.1291556000
_diffrn_orient_matrix_UB_12      -0.0720050000
_diffrn_orient_matrix_UB_13      0.0301836000
_diffrn_orient_matrix_UB_21      -0.1280893000
_diffrn_orient_matrix_UB_22      0.0822760000
_diffrn_orient_matrix_UB_23      -0.0105066000
_diffrn_orient_matrix_UB_31      -0.0323810000
_diffrn_orient_matrix_UB_32      -0.0383627000
_diffrn_orient_matrix_UB_33      -0.0790326000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3989
_reflns_number_total             4006
_reflns_odcompleteness_completeness 100.00
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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         0.149
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1882 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0218
_refine_ls_restrained_S_all      1.067
_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)+(0.0341P)²+0.3520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0559
_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.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C14(H14)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5), O10(H10)
;
_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
O1 O 0.62236(13) 0.24596(8) 0.46854(6) 0.0151(2) Uani 1 1 d . . . . .
O3 O 0.43839(13) 0.13589(8) 0.52103(7) 0.0165(2) Uani 1 1 d . . . . .
H3 H 0.393622 0.123469 0.481673 0.025 Uiso 1 1 calc GR . . . .
O4 O 0.35266(14) 0.34420(9) 0.43553(6) 0.0186(2) Uani 1 1 d . . . . .
O5 O 0.88723(14) 0.29768(9) 0.33760(7) 0.0190(2) Uani 1 1 d . . . . .
H5 H 0.795474 0.316540 0.329018 0.029 Uiso 1 1 calc GR . . . .
O6 O 0.03668(14) 0.37126(9) 0.62519(7) 0.0194(2) Uani 1 1 d . . . . .
O7 O 0.61387(14) 0.35611(8) 0.59275(7) 0.0158(2) Uani 1 1 d . . . . .
O8 O 0.93307(14) 0.09569(9) 0.65848(6) 0.0186(3) Uani 1 1 d . . . . .
O9 O 1.26517(14) 0.09884(9) 0.39273(7) 0.0194(2) Uani 1 1 d . . . . .
O11 O 0.67970(13) 0.18944(8) 0.61862(6) 0.0154(2) Uani 1 1 d . . . . .
O17 O 1.04554(14) 0.15899(9) 0.33664(7) 0.0183(2) Uani 1 1 d . . . . .
C2 C 0.49501(18) 0.23422(12) 0.52009(9) 0.0143(3) Uani 1 1 d . . . . .
C3 C 0.36097(19) 0.30904(11) 0.49790(9) 0.0146(3) Uani 1 1 d . . . . .
C4 C 0.24797(19) 0.32765(11) 0.55776(10) 0.0155(3) Uani 1 1 d . . . . .
C5 C 0.1004(2) 0.37317(12) 0.55615(10) 0.0169(3) Uani 1 1 d . . . . .
C7 C 0.1466(2) 0.32518(13) 0.67187(10) 0.0187(3) Uani 1 1 d . . . . .
H7 H 0.132462 0.315504 0.722423 0.022 Uiso 1 1 calc R . . . .
C8 C 0.2762(2) 0.29666(12) 0.63322(9) 0.0163(3) Uani 1 1 d . . . . .
C9 C 0.42536(19) 0.24247(12) 0.65694(9) 0.0166(3) Uani 1 1 d . . . . .
H9A H 0.403031 0.171275 0.662512 0.020 Uiso 1 1 calc R . . . .
H9B H 0.461455 0.268296 0.704305 0.020 Uiso 1 1 calc R . . . .
C10 C 0.55528(19) 0.25783(12) 0.59894(9) 0.0148(3) Uani 1 1 d . . . . .
C12 C 0.78918(19) 0.17146(11) 0.56395(9) 0.0144(3) Uani 1 1 d . . . . .
C13 C 0.9304(2) 0.12087(12) 0.58584(9) 0.0149(3) Uani 1 1 d . . . . .
C14 C 1.05054(19) 0.10210(12) 0.53461(9) 0.0158(3) Uani 1 1 d . . . . .
H14 H 1.145699 0.070423 0.547911 0.019 Uiso 1 1 calc R . . . .
C15 C 1.0213(2) 0.13320(12) 0.46203(10) 0.0154(3) Uani 1 1 d . . . . .
C16 C 1.1265(2) 0.12658(12) 0.39704(9) 0.0159(3) Uani 1 1 d . . . . .
C18 C 0.88550(19) 0.19600(12) 0.35672(9) 0.0159(3) Uani 1 1 d . . . . .
C19 C 0.88068(19) 0.17787(12) 0.43911(9) 0.0144(3) Uani 1 1 d . . . . .
C20 C 0.76160(19) 0.19844(11) 0.49062(9) 0.0139(3) Uani 1 1 d . . . . .
C21 C 0.0031(2) 0.42159(13) 0.49781(10) 0.0206(3) Uani 1 1 d . . . . .
H21A H -0.108635 0.413741 0.509149 0.031 Uiso 1 1 calc GR . . . .
H21B H 0.025887 0.390612 0.450981 0.031 Uiso 1 1 calc GR . . . .
H21C H 0.028960 0.491876 0.495398 0.031 Uiso 1 1 calc GR . . . .
C22 C 0.6692(2) 0.40088(13) 0.66026(9) 0.0198(3) Uani 1 1 d . . . . .
H22A H 0.734077 0.458557 0.649032 0.030 Uiso 1 1 calc GR . . . .
H22B H 0.731856 0.352814 0.687397 0.030 Uiso 1 1 calc GR . . . .
H22C H 0.578847 0.421252 0.689547 0.030 Uiso 1 1 calc GR . . . .
C23 C 1.0735(2) 0.04700(13) 0.68612(10) 0.0210(3) Uani 1 1 d . . . . .
H23A H 1.090777 -0.014483 0.659427 0.032 Uiso 1 1 calc GR . . . .
H23B H 1.059657 0.032328 0.737754 0.032 Uiso 1 1 calc GR . . . .
H23C H 1.164443 0.090411 0.679770 0.032 Uiso 1 1 calc GR . . . .
C24 C 0.7607(2) 0.13690(12) 0.31377(9) 0.0186(3) Uani 1 1 d . . . . .
H24A H 0.777166 0.146673 0.261678 0.028 Uiso 1 1 calc GR . . . .
H24B H 0.655496 0.159927 0.327095 0.028 Uiso 1 1 calc GR . . . .
H24C H 0.770535 0.066705 0.325362 0.028 Uiso 1 1 calc GR . . . .
O10 O 0.58571(16) 0.37035(10) 0.32251(7) 0.0241(3) Uani 1 1 d . . . . .
H10 H 0.533233 0.353874 0.358923 0.036 Uiso 1 1 calc GR . . . .
C25 C 0.5969(3) 0.47730(15) 0.31936(11) 0.0296(4) Uani 1 1 d . . . . .
H25A H 0.634943 0.497269 0.271413 0.044 Uiso 1 1 calc GR . . . .
H25B H 0.670322 0.500431 0.356595 0.044 Uiso 1 1 calc GR . . . .
H25C H 0.493095 0.506194 0.327971 0.044 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
O1 C2 1.4212(18) . ?
O1 C20 1.3808(18) . ?
O3 H3 0.8200 . ?
O3 C2 1.3903(19) . ?
O4 C3 1.222(2) . ?
O5 H5 0.8200 . ?
O5 C18 1.396(2) . ?
O6 C5 1.356(2) . ?
O6 C7 1.388(2) . ?
O7 C10 1.3995(19) . ?
O7 C22 1.4336(19) . ?
O8 C13 1.355(2) . ?
O8 C23 1.428(2) . ?
O9 C16 1.216(2) . ?
O11 C10 1.4248(19) . ?
O11 C12 1.3661(19) . ?
O17 C16 1.354(2) . ?
O17 C18 1.4680(19) . ?
C2 C3 1.549(2) . ?
C2 C10 1.543(2) . ?
C3 C4 1.456(2) . ?
C4 C5 1.372(2) . ?
C4 C8 1.444(2) . ?
C5 C21 1.478(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.342(2) . ?
C8 C9 1.500(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.521(2) . ?
C12 C13 1.413(2) . ?
C12 C20 1.392(2) . ?
C13 C14 1.386(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.396(2) . ?
C15 C16 1.468(2) . ?
C15 C19 1.379(2) . ?
C18 C19 1.509(2) . ?
C18 C24 1.517(2) . ?
C19 C20 1.388(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
O10 H10 0.8200 . ?
O10 C25 1.426(2) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C20 O1 C2 112.88(12) . . ?
C2 O3 H3 109.5 . . ?
C18 O5 H5 109.5 . . ?
C5 O6 C7 107.96(13) . . ?
C10 O7 C22 115.60(12) . . ?
C13 O8 C23 117.66(13) . . ?
C12 O11 C10 114.70(12) . . ?
C16 O17 C18 111.16(13) . . ?
O1 C2 C3 107.40(12) . . ?
O1 C2 C10 109.84(12) . . ?
O3 C2 O1 111.41(12) . . ?
O3 C2 C3 111.23(12) . . ?
O3 C2 C10 106.90(12) . . ?
C10 C2 C3 110.08(13) . . ?
O4 C3 C2 121.69(15) . . ?
O4 C3 C4 125.69(14) . . ?
C4 C3 C2 112.58(14) . . ?
C5 C4 C3 129.80(16) . . ?
C5 C4 C8 107.00(15) . . ?
C8 C4 C3 123.19(14) . . ?
O6 C5 C4 108.90(15) . . ?
O6 C5 C21 116.69(15) . . ?
C4 C5 C21 134.41(17) . . ?
O6 C7 H7 125.0 . . ?
C8 C7 O6 109.91(16) . . ?
C8 C7 H7 125.0 . . ?
C4 C8 C9 122.85(14) . . ?
C7 C8 C4 106.21(15) . . ?
C7 C8 C9 130.93(16) . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
C8 C9 C10 109.22(13) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
O7 C10 O11 111.20(13) . . ?
O7 C10 C2 103.29(12) . . ?
O7 C10 C9 115.41(13) . . ?
O11 C10 C2 109.74(12) . . ?
O11 C10 C9 105.13(12) . . ?
C9 C10 C2 112.14(13) . . ?
O11 C12 C13 115.98(14) . . ?
O11 C12 C20 122.19(14) . . ?
C20 C12 C13 121.79(15) . . ?
O8 C13 C12 113.73(14) . . ?
O8 C13 C14 126.19(15) . . ?
C14 C13 C12 120.08(15) . . ?
C13 C14 H14 121.7 . . ?
C13 C14 C15 116.59(15) . . ?
C15 C14 H14 121.7 . . ?
C14 C15 C16 128.98(15) . . ?
C19 C15 C14 123.92(15) . . ?
C19 C15 C16 107.09(15) . . ?
O9 C16 O17 121.28(15) . . ?
O9 C16 C15 129.60(16) . . ?
O17 C16 C15 109.12(14) . . ?
O5 C18 O17 104.72(12) . . ?
O5 C18 C19 113.54(13) . . ?
O5 C18 C24 112.47(13) . . ?
O17 C18 C19 102.39(12) . . ?
O17 C18 C24 108.87(12) . . ?
C19 C18 C24 113.81(14) . . ?
C15 C19 C18 110.04(14) . . ?
C15 C19 C20 119.48(15) . . ?
C20 C19 C18 130.48(14) . . ?
O1 C20 C12 122.14(14) . . ?
O1 C20 C19 119.87(14) . . ?
C19 C20 C12 117.99(14) . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O7 C22 H22A 109.5 . . ?
O7 C22 H22B 109.5 . . ?
O7 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O8 C23 H23A 109.5 . . ?
O8 C23 H23B 109.5 . . ?
O8 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 C24 H24A 109.5 . . ?
C18 C24 H24B 109.5 . . ?
C18 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C25 O10 H10 109.5 . . ?
O10 C25 H25A 109.5 . . ?
O10 C25 H25B 109.5 . . ?
O10 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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 1.332
_oxdiff_exptl_absorpt_empirical_full_min 0.681
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_chemical_compound_source        fungus
####################################################################### 
# 
# 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_zyh_zypc502
_database_code_depnum_ccdc_archive 'CCDC 1900801'
loop_
_audit_author_name
_audit_author_address
'yi zang'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2019-03-04 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H18 O10, C H4 O'
_chemical_formula_sum            'C21 H22 O11'
_chemical_formula_iupac          ?
_chemical_formula_weight         450.38
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.2302(4)
_cell_length_b                   14.4554(6)
_cell_length_c                   16.2394(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1932.01(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9830
_cell_measurement_theta_min      4.0943
_cell_measurement_theta_max      72.6955
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944

_exptl_absorpt_coefficient_mu    1.086
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            25161
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         72.82
_diffrn_reflns_theta_full        72.82
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             3833
_reflns_number_gt                3697
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1193
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_number_reflns         3833
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1518 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(9)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.2389(2) 0.58332(11) 0.23907(11) 0.0193(4) Uani d . . . 1 . .
O O2 0.2489(2) 0.40521(12) 0.24880(11) 0.0213(4) Uani d . . . 1 . .
O O3 0.6382(2) 0.36523(12) 0.52498(12) 0.0254(4) Uani d . . . 1 . .
O O4 0.6646(2) 0.51981(12) 0.53156(11) 0.0227(4) Uani d . . . 1 . .
O O5 0.3956(2) 0.69817(12) 0.35792(10) 0.0187(4) Uani d . . . 1 . .
O O6 0.0775(2) 0.96510(13) 0.13769(12) 0.0245(4) Uani d . . . 1 . .
O O7 0.3942(2) 0.87960(12) 0.33598(11) 0.0238(4) Uani d . . . 1 . .
O O8 0.4258(2) 0.69397(12) 0.19365(11) 0.0204(4) Uani d . . . 1 . .
O O9 0.1164(2) 0.71640(12) 0.34248(12) 0.0207(4) Uani d . . . 1 . .
H H9A 0.1053(19) 0.750(3) 0.382(3) 0.031 Uiso calc U . R 1 . .
O O10 0.5110(2) 0.65320(13) 0.54713(11) 0.0222(4) Uani d . . . 1 . .
H H10A 0.444(5) 0.6298(19) 0.5574(19) 0.033 Uiso calc U . R 1 . .
O O11 0.2487(3) 0.55315(15) 0.57688(13) 0.0313(5) Uani d . . . 1 . .
H H11A 0.215(3) 0.558(3) 0.622(3) 0.047 Uiso calc U . R 1 . .
C C1 0.2034(3) 1.05212(18) 0.24912(16) 0.0260(5) Uani d . . . 1 . .
H H1 0.31509 1.070623 0.236222 0.039 Uiso calc U . R 1 . .
H H7 0.19153 1.045078 0.308838 0.039 Uiso calc U . R 1 . .
H H8 0.127929 1.099644 0.229382 0.039 Uiso calc U . R 1 . .
C C2 0.1665(3) 0.96287(18) 0.20813(15) 0.0214(5) Uani d . . . 1 . .
C C3 0.2014(3) 0.87282(17) 0.22695(16) 0.0201(5) Uani d . . . 1 . .
C C4 0.1275(3) 0.81550(18) 0.16455(16) 0.0214(5) Uani d . . . 1 . .
C C5 0.1322(3) 0.71187(17) 0.16690(15) 0.0212(5) Uani d . . . 1 . .
H H5 0.1507 0.687439 0.110723 0.025 Uiso calc U . R 1 . .
H H6 0.026737 0.687788 0.186919 0.025 Uiso calc U . R 1 . .
C C6 0.2684(3) 0.67965(16) 0.22393(16) 0.0193(5) Uani d . . . 1 . .
C C7 0.3273(3) 0.54758(17) 0.30329(15) 0.0181(5) Uani d . . . 1 . .
C C8 0.3345(3) 0.44993(16) 0.30878(16) 0.0195(5) Uani d . . . 1 . .
C C9 0.2505(3) 0.30515(17) 0.25100(17) 0.0225(5) Uani d . . . 1 . .
H H16 0.358611 0.282662 0.235496 0.034 Uiso calc U . R 1 . .
H H3 0.169683 0.28105 0.212228 0.034 Uiso calc U . R 1 . .
H H2 0.22434 0.283953 0.306766 0.034 Uiso calc U . R 1 . .
C C10 0.4223(3) 0.40810(17) 0.37147(16) 0.0207(5) Uani d . . . 1 . .
H H4 0.426881 0.342709 0.376817 0.025 Uiso calc U . R 1 . .
C C11 0.5028(3) 0.46578(16) 0.42592(16) 0.0201(5) Uani d . . . 1 . .
C C12 0.6054(3) 0.44055(18) 0.49763(15) 0.0209(5) Uani d . . . 1 . .
C C13 0.5989(3) 0.60281(16) 0.49000(15) 0.0201(5) Uani d . . . 1 . .
C C14 0.4969(3) 0.56108(16) 0.42194(15) 0.0189(5) Uani d . . . 1 . .
C C15 0.4055(3) 0.60344(16) 0.36075(15) 0.0181(5) Uani d . . . 1 . .
C C16 0.2676(3) 0.73146(16) 0.30712(15) 0.0182(5) Uani d . . . 1 . .
C C17 0.0562(3) 0.87456(18) 0.11205(17) 0.0237(5) Uani d . . . 1 . .
H H9 -0.001131 0.856684 0.063824 0.028 Uiso calc U . R 1 . .
C C18 0.2992(3) 0.83618(17) 0.29371(15) 0.0185(5) Uani d . . . 1 . .
C C19 0.4578(4) 0.6590(2) 0.11247(18) 0.0316(6) Uani d . . . 1 . .
H H12 0.401731 0.599833 0.105054 0.047 Uiso calc U . R 1 . .
H H11 0.575049 0.650019 0.105524 0.047 Uiso calc U . R 1 . .
H H10 0.418597 0.703459 0.071442 0.047 Uiso calc U . R 1 . .
C C20 0.7398(3) 0.66189(17) 0.46106(16) 0.0226(5) Uani d . . . 1 . .
H H15 0.698334 0.713976 0.42864 0.034 Uiso calc U . R 1 . .
H H13 0.812751 0.624484 0.426913 0.034 Uiso calc U . R 1 . .
H H14 0.799443 0.685449 0.508894 0.034 Uiso calc U . R 1 . .
C C21 0.1194(4) 0.5683(2) 0.51944(17) 0.0289(6) Uani d . . . 1 . .
H H17 0.019846 0.539154 0.540015 0.043 Uiso calc U . R 1 . .
H H19 0.148387 0.54129 0.466097 0.043 Uiso calc U . R 1 . .
H H18 0.101359 0.634948 0.512926 0.043 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.373(3) ?
O1 C6 . 1.435(3) ?
O2 C8 . 1.365(3) ?
O2 C9 . 1.447(3) ?
O3 C12 . 1.206(3) ?
O4 C12 . 1.361(3) ?
O4 C13 . 1.479(3) ?
O5 C15 . 1.373(3) ?
O5 C16 . 1.422(3) ?
O6 C2 . 1.359(3) ?
O6 C17 . 1.385(3) ?
O7 C18 . 1.215(3) ?
O8 C6 . 1.401(3) ?
O8 C19 . 1.436(3) ?
O9 C16 . 1.388(3) ?
O9 H9A . 0.81(4) ?
O10 C13 . 1.384(3) ?
O10 H10A . 0.67(4) ?
O11 C21 . 1.432(3) ?
O11 H11A . 0.79(5) ?
C1 C2 . 1.483(4) ?
C1 H1 . 0.98 ?
C1 H7 . 0.98 ?
C1 H8 . 0.98 ?
C2 C3 . 1.368(3) ?
C3 C4 . 1.443(3) ?
C3 C18 . 1.450(3) ?
C4 C17 . 1.342(4) ?
C4 C5 . 1.499(3) ?
C5 C6 . 1.527(3) ?
C5 H5 . 0.99 ?
C5 H6 . 0.99 ?
C6 C16 . 1.545(3) ?
C7 C15 . 1.392(3) ?
C7 C8 . 1.416(3) ?
C8 C10 . 1.387(4) ?
C9 H16 . 0.98 ?
C9 H3 . 0.98 ?
C9 H2 . 0.98 ?
C10 C11 . 1.385(4) ?
C10 H4 . 0.95 ?
C11 C14 . 1.380(3) ?
C11 C12 . 1.484(3) ?
C13 C14 . 1.513(3) ?
C13 C20 . 1.515(4) ?
C14 C15 . 1.389(4) ?
C16 C18 . 1.551(3) ?
C17 H9 . 0.95 ?
C19 H12 . 0.98 ?
C19 H11 . 0.98 ?
C19 H10 . 0.98 ?
C20 H15 . 0.98 ?
C20 H13 . 0.98 ?
C20 H14 . 0.98 ?
C21 H17 . 0.98 ?
C21 H19 . 0.98 ?
C21 H18 . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 C6 . . 113.95(18) ?
C8 O2 C9 . . 116.82(19) ?
C12 O4 C13 . . 111.55(19) ?
C15 O5 C16 . . 113.63(18) ?
C2 O6 C17 . . 107.4(2) ?
C6 O8 C19 . . 116.1(2) ?
C16 O9 H9A . . 109.5 ?
C13 O10 H10A . . 109.5 ?
C21 O11 H11A . . 109.5 ?
C2 C1 H1 . . 109.5 ?
C2 C1 H7 . . 109.5 ?
H1 C1 H7 . . 109.5 ?
C2 C1 H8 . . 109.5 ?
H1 C1 H8 . . 109.5 ?
H7 C1 H8 . . 109.5 ?
O6 C2 C3 . . 108.9(2) ?
O6 C2 C1 . . 117.9(2) ?
C3 C2 C1 . . 133.2(2) ?
C2 C3 C4 . . 107.5(2) ?
C2 C3 C18 . . 129.1(2) ?
C4 C3 C18 . . 123.3(2) ?
C17 C4 C3 . . 105.4(2) ?
C17 C4 C5 . . 131.6(2) ?
C3 C4 C5 . . 123.0(2) ?
C4 C5 C6 . . 109.8(2) ?
C4 C5 H5 . . 109.7 ?
C6 C5 H5 . . 109.7 ?
C4 C5 H6 . . 109.7 ?
C6 C5 H6 . . 109.7 ?
H5 C5 H6 . . 108.2 ?
O8 C6 O1 . . 111.1(2) ?
O8 C6 C5 . . 114.9(2) ?
O1 C6 C5 . . 106.0(2) ?
O8 C6 C16 . . 103.85(19) ?
O1 C6 C16 . . 108.7(2) ?
C5 C6 C16 . . 112.3(2) ?
O1 C7 C15 . . 122.4(2) ?
O1 C7 C8 . . 116.4(2) ?
C15 C7 C8 . . 121.1(2) ?
O2 C8 C10 . . 125.9(2) ?
O2 C8 C7 . . 113.9(2) ?
C10 C8 C7 . . 120.2(2) ?
O2 C9 H16 . . 109.5 ?
O2 C9 H3 . . 109.5 ?
H16 C9 H3 . . 109.5 ?
O2 C9 H2 . . 109.5 ?
H16 C9 H2 . . 109.5 ?
H3 C9 H2 . . 109.5 ?
C11 C10 C8 . . 117.1(2) ?
C11 C10 H4 . . 121.4 ?
C8 C10 H4 . . 121.4 ?
C14 C11 C10 . . 123.7(2) ?
C14 C11 C12 . . 107.6(2) ?
C10 C11 C12 . . 128.7(2) ?
O3 C12 O4 . . 122.0(2) ?
O3 C12 C11 . . 129.6(2) ?
O4 C12 C11 . . 108.3(2) ?
O10 C13 O4 . . 108.19(19) ?
O10 C13 C14 . . 114.2(2) ?
O4 C13 C14 . . 102.28(18) ?
O10 C13 C20 . . 108.2(2) ?
O4 C13 C20 . . 108.6(2) ?
C14 C13 C20 . . 115.0(2) ?
C11 C14 C15 . . 119.5(2) ?
C11 C14 C13 . . 110.1(2) ?
C15 C14 C13 . . 130.3(2) ?
O5 C15 C14 . . 119.7(2) ?
O5 C15 C7 . . 121.9(2) ?
C14 C15 C7 . . 118.3(2) ?
O9 C16 O5 . . 111.79(19) ?
O9 C16 C6 . . 106.84(19) ?
O5 C16 C6 . . 109.89(19) ?
O9 C16 C18 . . 111.18(19) ?
O5 C16 C18 . . 106.71(19) ?
C6 C16 C18 . . 110.46(19) ?
C4 C17 O6 . . 110.8(2) ?
C4 C17 H9 . . 124.6 ?
O6 C17 H9 . . 124.6 ?
O7 C18 C3 . . 126.2(2) ?
O7 C18 C16 . . 122.2(2) ?
C3 C18 C16 . . 111.6(2) ?
O8 C19 H12 . . 109.5 ?
O8 C19 H11 . . 109.5 ?
H12 C19 H11 . . 109.5 ?
O8 C19 H10 . . 109.5 ?
H12 C19 H10 . . 109.5 ?
H11 C19 H10 . . 109.5 ?
C13 C20 H15 . . 109.5 ?
C13 C20 H13 . . 109.5 ?
H15 C20 H13 . . 109.5 ?
C13 C20 H14 . . 109.5 ?
H15 C20 H14 . . 109.5 ?
H13 C20 H14 . . 109.5 ?
O11 C21 H17 . . 109.5 ?
O11 C21 H19 . . 109.5 ?
H17 C21 H19 . . 109.5 ?
O11 C21 H18 . . 109.5 ?
H17 C21 H18 . . 109.5 ?
H19 C21 H18 . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C17 O6 C2 C3 . . . . 0.0(3) ?
C17 O6 C2 C1 . . . . -178.8(2) ?
O6 C2 C3 C4 . . . . -0.7(3) ?
C1 C2 C3 C4 . . . . 177.9(3) ?
O6 C2 C3 C18 . . . . 176.8(2) ?
C1 C2 C3 C18 . . . . -4.6(5) ?
C2 C3 C4 C17 . . . . 1.0(3) ?
C18 C3 C4 C17 . . . . -176.6(2) ?
C2 C3 C4 C5 . . . . -176.7(2) ?
C18 C3 C4 C5 . . . . 5.6(4) ?
C17 C4 C5 C6 . . . . 163.7(3) ?
C3 C4 C5 C6 . . . . -19.2(3) ?
C19 O8 C6 O1 . . . . 68.2(3) ?
C19 O8 C6 C5 . . . . -52.1(3) ?
C19 O8 C6 C16 . . . . -175.2(2) ?
C7 O1 C6 O8 . . . . 68.4(2) ?
C7 O1 C6 C5 . . . . -166.14(19) ?
C7 O1 C6 C16 . . . . -45.2(3) ?
C4 C5 C6 O8 . . . . -71.2(3) ?
C4 C5 C6 O1 . . . . 165.7(2) ?
C4 C5 C6 C16 . . . . 47.2(3) ?
C6 O1 C7 C15 . . . . 15.3(3) ?
C6 O1 C7 C8 . . . . -165.1(2) ?
C9 O2 C8 C10 . . . . -0.1(4) ?
C9 O2 C8 C7 . . . . -179.7(2) ?
O1 C7 C8 O2 . . . . -0.8(3) ?
C15 C7 C8 O2 . . . . 178.8(2) ?
O1 C7 C8 C10 . . . . 179.5(2) ?
C15 C7 C8 C10 . . . . -0.9(4) ?
O2 C8 C10 C11 . . . . 179.2(2) ?
C7 C8 C10 C11 . . . . -1.2(4) ?
C8 C10 C11 C14 . . . . 1.5(4) ?
C8 C10 C11 C12 . . . . -179.6(2) ?
C13 O4 C12 O3 . . . . -176.6(2) ?
C13 O4 C12 C11 . . . . 3.9(3) ?
C14 C11 C12 O3 . . . . 177.3(3) ?
C10 C11 C12 O3 . . . . -1.7(5) ?
C14 C11 C12 O4 . . . . -3.2(3) ?
C10 C11 C12 O4 . . . . 177.8(2) ?
C12 O4 C13 O10 . . . . 117.8(2) ?
C12 O4 C13 C14 . . . . -3.0(3) ?
C12 O4 C13 C20 . . . . -125.0(2) ?
C10 C11 C14 C15 . . . . 0.3(4) ?
C12 C11 C14 C15 . . . . -178.8(2) ?
C10 C11 C14 C13 . . . . -179.7(2) ?
C12 C11 C14 C13 . . . . 1.3(3) ?
O10 C13 C14 C11 . . . . -115.7(2) ?
O4 C13 C14 C11 . . . . 0.9(3) ?
C20 C13 C14 C11 . . . . 118.4(2) ?
O10 C13 C14 C15 . . . . 64.4(3) ?
O4 C13 C14 C15 . . . . -179.0(2) ?
C20 C13 C14 C15 . . . . -61.5(3) ?
C16 O5 C15 C14 . . . . -164.6(2) ?
C16 O5 C15 C7 . . . . 16.0(3) ?
C11 C14 C15 O5 . . . . 178.2(2) ?
C13 C14 C15 O5 . . . . -1.9(4) ?
C11 C14 C15 C7 . . . . -2.4(4) ?
C13 C14 C15 C7 . . . . 177.5(2) ?
O1 C7 C15 O5 . . . . 1.7(4) ?
C8 C7 C15 O5 . . . . -177.9(2) ?
O1 C7 C15 C14 . . . . -177.7(2) ?
C8 C7 C15 C14 . . . . 2.7(4) ?
C15 O5 C16 O9 . . . . 71.8(2) ?
C15 O5 C16 C6 . . . . -46.7(2) ?
C15 O5 C16 C18 . . . . -166.47(19) ?
O8 C6 C16 O9 . . . . -177.29(18) ?
O1 C6 C16 O9 . . . . -59.0(2) ?
C5 C6 C16 O9 . . . . 58.0(2) ?
O8 C6 C16 O5 . . . . -55.8(2) ?
O1 C6 C16 O5 . . . . 62.5(2) ?
C5 C6 C16 O5 . . . . 179.5(2) ?
O8 C6 C16 C18 . . . . 61.7(2) ?
O1 C6 C16 C18 . . . . 179.98(19) ?
C5 C6 C16 C18 . . . . -63.1(3) ?
C3 C4 C17 O6 . . . . -1.0(3) ?
C5 C4 C17 O6 . . . . 176.5(2) ?
C2 O6 C17 C4 . . . . 0.7(3) ?
C2 C3 C18 O7 . . . . -15.5(4) ?
C4 C3 C18 O7 . . . . 161.6(2) ?
C2 C3 C18 C16 . . . . 163.8(2) ?
C4 C3 C18 C16 . . . . -19.1(3) ?
O9 C16 C18 O7 . . . . 107.1(3) ?
O5 C16 C18 O7 . . . . -15.0(3) ?
C6 C16 C18 O7 . . . . -134.5(3) ?
O9 C16 C18 C3 . . . . -72.3(2) ?
O5 C16 C18 C3 . . . . 165.59(19) ?
C6 C16 C18 C3 . . . . 46.2(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O9 H9A O10 2_466 0.81 1.97 2.742(3) 158.9 ?
O10 H10A O11 . 0.67 1.97 2.643(3) 173.9 ?
O11 H11A O2 4_565 0.79 2.14 2.856(3) 150.3 ?
C9 H16 O8 3_645 0.98 2.47 3.238(3) 134.7 ?
C19 H12 O11 4_564 0.98 2.58 3.554(4) 176.7 ?
C21 H17 O7 2_466 0.98 2.55 3.084(4) 114.2 ?



####################################################################### 
# 
# 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_20181203_zy-pc-25
_database_code_depnum_ccdc_archive 'CCDC 1883408'
loop_
_audit_author_name
_audit_author_address
'yi zang'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2018-12-06 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_audit_creation_date             2018-12-06
_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         'C22 H23 N O9'
_chemical_formula_sum            'C22 H23 N O9'
_chemical_formula_weight         445.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.26703(5)
_cell_length_b                   13.79202(8)
_cell_length_c                   17.73644(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.3917(6)
_cell_angle_gamma                90
_cell_volume                     1975.18(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25467
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.6880
_cell_measurement_theta_min      3.1860
_shelx_estimated_absorpt_T_max   0.890
_shelx_estimated_absorpt_T_min   0.762
_exptl_absorpt_coefficient_mu    0.993
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            44113
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.957
_diffrn_reflns_theta_min         4.097
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     51.00  82.00   0.50    0.50    --    0.00  57.00-120.00   62
  2  ω    -22.00   7.00   0.50    0.50    --    0.00  57.00-120.00   58
  3  ω      6.00  46.00   0.50    0.50    --    0.00  38.00  60.00   80
  4  ω    -37.00  10.00   0.50    0.50    --    0.00 -38.00  60.00   94
  5  ω     20.00  89.00   0.50    0.50    --    0.00  38.00 -30.00  138
  6  ω     -5.00  26.00   0.50    0.50    --    0.00  57.00  90.00   62
  7  ω    -16.00  77.00   0.50    0.50    --    0.00  19.00 120.00  186
  8  ω    -17.00  61.00   0.50    0.50    --    0.00  57.00-180.00  156
  9  ω     38.00  88.00   0.50    0.50    --    0.00  57.00  90.00  100
 10  ω    -30.00   7.00   0.50    0.50    --    0.00 -82.00 -30.00   74
 11  ω     18.00  44.00   0.50    0.50    --    0.00  57.00-120.00   52
 12  ω    -17.00  16.00   0.50    0.50    --    0.00  38.00 -30.00   66
 13  ω     69.00  95.00   0.50    0.60    --   94.60  73.00  53.29   52
 14  ω     68.00 184.00   0.50    0.60    --   94.60  70.00-174.62  232
 15  ω     69.00  95.00   0.50    0.60    --   94.60  68.00  25.71   52
 16  ω    143.00 169.00   0.50    0.60    --   94.60  67.00 -98.93   52
 17  ω     69.00 129.00   0.50    0.60    --   94.60  67.00 -98.93  120
 18  ω    131.00 157.00   0.50    0.60    --   94.60  70.00 -51.85   52
 19  ω     66.00  91.00   0.50    0.60    --   94.60  74.00   0.40   50
 20  ω     68.00 178.00   0.50    0.60    --   94.60  69.00 105.10  220
 21  ω     69.00  95.00   0.50    0.60    --   94.60  73.00 123.44   52
 22  ω    145.00 174.00   0.50    0.60    --   94.60  69.00  72.83   58
 23  ω     68.00 119.00   0.50    0.60    --   94.60  69.00 170.02  102
 24  ω    123.00 184.00   0.50    0.60    --   94.60  69.00 170.02  122
 25  ω     67.00  93.00   0.50    0.60    --   94.60  73.00  92.26   52
 26  ω     69.00 100.00   0.50    0.60    --   94.60  66.00  91.65   62
 27  ω     70.00 184.00   0.50    0.60    --   94.60  65.00 123.22  228
 28  ω     30.00 110.00   0.50    0.60    --   94.60 -82.00  90.00  160
 29  ω      6.00 126.00   0.50    0.60    --   94.60 -82.00 -90.00  240
 30  ω     71.00 112.00   0.50    0.60    --   94.60  61.00 -71.56   82
 31  ω    108.00 183.00   0.50    0.60    --   94.60  65.00-136.48  150
 32  ω     68.00 137.00   0.50    0.60    --   94.60  69.00  72.83  138
 33  ω     68.00  96.00   0.50    0.60    --   94.60  70.00 -51.85   56
 34  ω      5.00 124.00   0.50    0.60    --   94.60 -77.00 120.00  238
 35  ω     70.00  96.00   0.50    0.60    --   94.60  65.00-136.48   52
 36  ω     71.00 184.00   0.50    0.60    --   94.60  61.00   0.00  226
 37  ω     71.00 184.00   0.50    0.60    --   94.60  61.00 -60.00  226
 38  ω     71.00  97.00   0.50    0.60    --   94.60  61.00-150.00   52
 39  ω     71.00  97.00   0.50    0.60    --   94.60  63.00-113.10   52
 40  ω     51.00  78.00   0.50    0.60    --   94.60 -82.00 -60.00   54
 41  ω     92.00 123.00   0.50    0.60    --   94.60 -82.00 -60.00   62
 42  ω     71.00  97.00   0.50    0.60    --   94.60  61.00-120.00   52
 43  ω     70.00 132.00   0.50    0.60    --   94.60  65.00-108.84  124
 44  ω     70.00 183.00   0.50    0.60    --   94.60  65.00  60.56  226
 45  ω     76.00 102.00   0.50    0.60    --   94.60  45.00-120.00   52
 46  ω     71.00 129.00   0.50    0.60    --   94.60  61.00 -30.00  116
 47  ω    138.00 165.00   0.50    0.60    --   94.60  61.00 -30.00   54
 48  ω     90.00 122.00   0.50    0.60    --   94.60 -82.00   0.00   64
 49  ω     45.00  79.00   0.50    0.60    --   94.60 -82.00   0.00   68
 50  ω    101.00 126.00   0.50    0.60    --   94.60  71.00  36.71   50
 51  ω     47.00 125.00   0.50    0.60    --   94.60 -82.00-180.00  156
 52  ω     67.00  93.00   0.50    0.60    --   94.60  71.00  36.71   52
 53  ω    147.00 172.00   0.50    0.60    --   94.60  68.00  25.71   50
 54  ω     66.00  91.00   0.50    0.60    --   94.60  75.00 151.85   50
 55  ω     70.00 178.00   0.50    0.60    --   94.60  63.00 -19.63  216
 56  ω     68.00  94.00   0.50    0.60    --   94.60  70.00 143.68   52
;
_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      -0.1735227000
_diffrn_orient_matrix_UB_12      -0.0235014000
_diffrn_orient_matrix_UB_13      -0.0484954000
_diffrn_orient_matrix_UB_21      -0.0402503000
_diffrn_orient_matrix_UB_22      -0.0569609000
_diffrn_orient_matrix_UB_23      0.0684322000
_diffrn_orient_matrix_UB_31      -0.0684681000
_diffrn_orient_matrix_UB_32      0.0931364000
_diffrn_orient_matrix_UB_33      0.0295488000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3765
_reflns_number_total             3987
_reflns_odcompleteness_completeness 100.00
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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         0.241
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.065
_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)+(0.0476P)²+0.7808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0913
_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. Rigid bond restraints
 O27, C16
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C16 \\sim O27: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
4.a Ternary CH refined with riding coordinates:
 C18(H18)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C24(H24A,H24B), C25(H25A,H25B)
4.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C7(H7)
4.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C23(H23A,H23B,
 H23C)
4.e Idealised tetrahedral OH refined as rotating group:
 O29(H29), O26(H26)
;
_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
O11 O 0.26712(10) 0.83245(6) 0.25244(5) 0.02109(19) Uani 1 1 d . . . . .
O1 O 0.28422(10) 0.80436(6) 0.41347(5) 0.02065(19) Uani 1 1 d . . . . .
O31 O 0.22518(10) 0.96602(6) 0.32664(5) 0.02248(19) Uani 1 1 d . . . . .
O27 O 0.93723(10) 0.61881(6) 0.43200(5) 0.0234(2) Uani 1 1 d . U . . .
O29 O 0.06431(10) 0.72938(6) 0.33037(5) 0.02221(19) Uani 1 1 d . . . . .
H29 H 0.0297 0.6996 0.3637 0.033 Uiso 1 1 calc GR . . . .
O28 O 0.49406(11) 0.76990(7) 0.18597(5) 0.0243(2) Uani 1 1 d . . . . .
O6 O -0.35119(11) 1.00429(7) 0.30218(5) 0.0275(2) Uani 1 1 d . . . . .
O26 O 0.73889(11) 0.43669(7) 0.49075(5) 0.0278(2) Uani 1 1 d . . . . .
H26 H 0.8325 0.4148 0.4946 0.042 Uiso 1 1 calc GR . . . .
O30 O 0.02605(12) 0.86002(7) 0.47311(5) 0.0289(2) Uani 1 1 d . . . . .
N17 N 0.74749(12) 0.64543(7) 0.50842(6) 0.0204(2) Uani 1 1 d . . . . .
C13 C 0.52609(15) 0.75589(9) 0.26356(7) 0.0201(2) Uani 1 1 d . . . . .
C20 C 0.40931(14) 0.77484(8) 0.37827(7) 0.0192(2) Uani 1 1 d . . . . .
C12 C 0.40113(14) 0.78946(9) 0.29995(7) 0.0193(2) Uani 1 1 d . . . . .
C19 C 0.54786(14) 0.72786(8) 0.42117(7) 0.0195(2) Uani 1 1 d . . . . .
C16 C 0.80209(14) 0.65026(9) 0.44244(7) 0.0203(2) Uani 1 1 d . U . . .
C15 C 0.67328(14) 0.69996(9) 0.38510(7) 0.0198(2) Uani 1 1 d . . . . .
C2 C 0.13003(14) 0.81774(9) 0.36016(7) 0.0200(2) Uani 1 1 d . . . . .
C14 C 0.66642(14) 0.71207(9) 0.30649(7) 0.0207(2) Uani 1 1 d . . . . .
H14 H 0.7523 0.6916 0.2839 0.025 Uiso 1 1 calc R . . . .
C8 C -0.13315(15) 0.93190(9) 0.27065(7) 0.0228(3) Uani 1 1 d . . . . .
C4 C -0.12295(15) 0.92166(9) 0.35253(7) 0.0226(3) Uani 1 1 d . . . . .
C18 C 0.58717(14) 0.69500(9) 0.50409(7) 0.0207(2) Uani 1 1 d . . . . .
H18 H 0.5040 0.6478 0.5124 0.025 Uiso 1 1 calc R . . . .
C10 C 0.15654(14) 0.88010(9) 0.29178(7) 0.0202(2) Uani 1 1 d . . . . .
C3 C 0.01053(15) 0.86912(9) 0.40395(7) 0.0219(2) Uani 1 1 d . . . . .
C9 C -0.00466(15) 0.89209(9) 0.23141(7) 0.0230(3) Uani 1 1 d . . . . .
H9A H 0.0122 0.9360 0.1911 0.028 Uiso 1 1 calc R . . . .
H9B H -0.0403 0.8299 0.2081 0.028 Uiso 1 1 calc R . . . .
C24 C 0.81561(15) 0.57931(9) 0.57137(7) 0.0227(3) Uani 1 1 d . . . . .
H24A H 0.8047 0.6079 0.6200 0.027 Uiso 1 1 calc R . . . .
H24B H 0.9326 0.5694 0.5732 0.027 Uiso 1 1 calc R . . . .
C5 C -0.25825(15) 0.96744(9) 0.36871(8) 0.0246(3) Uani 1 1 d . . . . .
C7 C -0.27307(15) 0.98186(9) 0.24299(8) 0.0263(3) Uani 1 1 d . . . . .
H7 H -0.3115 0.9988 0.1915 0.032 Uiso 1 1 calc R . . . .
C25 C 0.72699(15) 0.48236(9) 0.56094(7) 0.0242(3) Uani 1 1 d . . . . .
H25A H 0.7745 0.4402 0.6038 0.029 Uiso 1 1 calc R . . . .
H25B H 0.6112 0.4921 0.5617 0.029 Uiso 1 1 calc R . . . .
C26 C 0.60189(17) 0.77561(10) 0.56372(7) 0.0269(3) Uani 1 1 d . . . . .
H26A H 0.6365 0.7487 0.6145 0.040 Uiso 1 1 calc GR . . . .
H26B H 0.4964 0.8067 0.5592 0.040 Uiso 1 1 calc GR . . . .
H26C H 0.6821 0.8223 0.5550 0.040 Uiso 1 1 calc GR . . . .
C22 C 0.24922(17) 1.04226(9) 0.27532(8) 0.0274(3) Uani 1 1 d . . . . .
H22A H 0.3088 1.0176 0.2386 0.041 Uiso 1 1 calc GR . . . .
H22B H 0.3114 1.0938 0.3044 0.041 Uiso 1 1 calc GR . . . .
H22C H 0.1435 1.0665 0.2486 0.041 Uiso 1 1 calc GR . . . .
C21 C -0.31766(16) 0.98566(10) 0.44033(8) 0.0293(3) Uani 1 1 d . . . . .
H21A H -0.3082 1.0535 0.4525 0.044 Uiso 1 1 calc GR . . . .
H21B H -0.2519 0.9491 0.4819 0.044 Uiso 1 1 calc GR . . . .
H21C H -0.4314 0.9662 0.4331 0.044 Uiso 1 1 calc GR . . . .
C23 C 0.60327(17) 0.72474(11) 0.14389(7) 0.0310(3) Uani 1 1 d . . . . .
H23A H 0.5640 0.7365 0.0897 0.047 Uiso 1 1 calc GR . . . .
H23B H 0.6065 0.6562 0.1534 0.047 Uiso 1 1 calc GR . . . .
H23C H 0.7125 0.7513 0.1603 0.047 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
O11 C12 1.3742(14) . ?
O11 C10 1.4242(14) . ?
O1 C20 1.3791(14) . ?
O1 C2 1.4267(14) . ?
O31 C10 1.3992(15) . ?
O31 C22 1.4323(15) . ?
O27 C16 1.2488(15) . ?
O29 H29 0.8200 . ?
O29 C2 1.3915(15) . ?
O28 C13 1.3582(14) . ?
O28 C23 1.4317(15) . ?
O6 C5 1.3608(16) . ?
O6 C7 1.3807(17) . ?
O26 H26 0.8200 . ?
O26 C25 1.4175(15) . ?
O30 C3 1.2122(15) . ?
N17 C16 1.3432(16) . ?
N17 C18 1.4786(15) . ?
N17 C24 1.4578(15) . ?
C13 C12 1.4087(17) . ?
C13 C14 1.3827(17) . ?
C20 C12 1.3908(16) . ?
C20 C19 1.3916(16) . ?
C19 C15 1.3846(17) . ?
C19 C18 1.5062(16) . ?
C16 C15 1.4742(16) . ?
C15 C14 1.3932(17) . ?
C2 C10 1.5403(16) . ?
C2 C3 1.5527(16) . ?
C14 H14 0.9300 . ?
C8 C4 1.4434(17) . ?
C8 C9 1.4939(17) . ?
C8 C7 1.3452(17) . ?
C4 C3 1.4638(17) . ?
C4 C5 1.3675(17) . ?
C18 H18 0.9800 . ?
C18 C26 1.5213(17) . ?
C10 C9 1.5288(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.5168(18) . ?
C5 C21 1.4784(19) . ?
C7 H7 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C12 O11 C10 114.61(9) . . ?
C20 O1 C2 112.85(9) . . ?
C10 O31 C22 116.07(9) . . ?
C2 O29 H29 109.5 . . ?
C13 O28 C23 117.30(10) . . ?
C5 O6 C7 107.85(10) . . ?
C25 O26 H26 109.5 . . ?
C16 N17 C18 113.38(9) . . ?
C16 N17 C24 123.47(10) . . ?
C24 N17 C18 121.58(10) . . ?
O28 C13 C12 114.51(10) . . ?
O28 C13 C14 125.33(11) . . ?
C14 C13 C12 120.16(11) . . ?
O1 C20 C12 121.92(10) . . ?
O1 C20 C19 119.94(10) . . ?
C12 C20 C19 118.13(11) . . ?
O11 C12 C13 115.77(10) . . ?
O11 C12 C20 122.35(10) . . ?
C20 C12 C13 121.79(11) . . ?
C20 C19 C18 130.83(11) . . ?
C15 C19 C20 119.13(11) . . ?
C15 C19 C18 109.96(10) . . ?
O27 C16 N17 126.20(11) . . ?
O27 C16 C15 126.58(11) . . ?
N17 C16 C15 107.22(10) . . ?
C19 C15 C16 108.19(10) . . ?
C19 C15 C14 123.74(11) . . ?
C14 C15 C16 127.90(11) . . ?
O1 C2 C10 109.64(9) . . ?
O1 C2 C3 107.55(9) . . ?
O29 C2 O1 111.03(9) . . ?
O29 C2 C10 107.46(9) . . ?
O29 C2 C3 110.55(9) . . ?
C10 C2 C3 110.63(9) . . ?
C13 C14 C15 116.92(11) . . ?
C13 C14 H14 121.5 . . ?
C15 C14 H14 121.5 . . ?
C4 C8 C9 122.61(11) . . ?
C7 C8 C4 106.09(11) . . ?
C7 C8 C9 131.31(12) . . ?
C8 C4 C3 123.28(11) . . ?
C5 C4 C8 106.99(11) . . ?
C5 C4 C3 129.72(12) . . ?
N17 C18 C19 101.13(9) . . ?
N17 C18 H18 109.6 . . ?
N17 C18 C26 111.39(10) . . ?
C19 C18 H18 109.6 . . ?
C19 C18 C26 115.29(10) . . ?
C26 C18 H18 109.6 . . ?
O11 C10 C2 110.05(9) . . ?
O11 C10 C9 105.16(9) . . ?
O31 C10 O11 111.42(9) . . ?
O31 C10 C2 103.75(9) . . ?
O31 C10 C9 115.32(10) . . ?
C9 C10 C2 111.22(10) . . ?
O30 C3 C2 121.23(11) . . ?
O30 C3 C4 125.71(11) . . ?
C4 C3 C2 112.94(10) . . ?
C8 C9 C10 108.28(10) . . ?
C8 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
C10 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
N17 C24 H24A 109.4 . . ?
N17 C24 H24B 109.4 . . ?
N17 C24 C25 111.16(10) . . ?
H24A C24 H24B 108.0 . . ?
C25 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
O6 C5 C4 108.99(11) . . ?
O6 C5 C21 116.85(11) . . ?
C4 C5 C21 134.14(12) . . ?
O6 C7 H7 125.0 . . ?
C8 C7 O6 110.08(11) . . ?
C8 C7 H7 125.0 . . ?
O26 C25 C24 112.10(10) . . ?
O26 C25 H25A 109.2 . . ?
O26 C25 H25B 109.2 . . ?
C24 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C18 C26 H26A 109.5 . . ?
C18 C26 H26B 109.5 . . ?
C18 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O31 C22 H22A 109.5 . . ?
O31 C22 H22B 109.5 . . ?
O31 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O28 C23 H23A 109.5 . . ?
O28 C23 H23B 109.5 . . ?
O28 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.743
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
