# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_20210601_ps-7
_database_code_depnum_ccdc_archive 'CCDC 2321677'
loop_
_audit_author_name
_audit_author_address
'Hanli Ruan'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2023-12-25 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2021-09-24
_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         'C18 H20 O5, 2(H2 O)'
_chemical_formula_sum            'C18 H24 O7'
_chemical_formula_weight         352.37
_chemical_absolute_configuration ad
_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           19
_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.55080(10)
_cell_length_b                   12.47630(10)
_cell_length_c                   16.58680(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1769.52(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13593
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4990
_cell_measurement_theta_min      4.4180
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.727
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77353
_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    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18877
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.924
_diffrn_reflns_theta_min         4.435
_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 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00   0.00   0.50    0.50    --    0.00  73.00 107.49   54
  2  ω    -28.00  29.00   0.50    0.50    --    0.00 -82.00 120.00  114
  3  ω    -28.00  31.00   0.50    0.50    --    0.00 -82.00 -30.00  118
  4  ω    -32.00  28.00   0.50    0.50    --    0.00 -82.00-150.00  120
  5  ω    -27.00  -1.00   0.50    0.50    --    0.00 -82.00  90.00   52
  6  ω    -16.00  39.00   0.50    0.50    --    0.00  38.00   0.00  110
  7  ω     11.00  86.00   0.50    0.50    --   94.60 -77.00  30.00  150
  8  ω     41.00 125.00   0.50    0.50    --   94.60 -82.00 -90.00  168
  9  ω      5.00 100.00   0.50    0.50    --   94.60 -30.00-150.00  190
 10  ω     82.00 151.00   0.50    0.50    --   94.60  77.00-120.00  138
 11  ω     12.00 108.00   0.50    0.50    --   94.60 -15.00-120.00  192
 12  ω     81.00 126.00   0.50    0.50    --   94.60 -82.00   0.00   90
 13  ω     85.00 171.00   0.50    0.50    --   94.60  77.00-180.00  172
 14  ω     71.00 173.00   0.50    0.50    --   94.60  61.00 -30.00  204
 15  ω      6.00  97.00   0.50    0.50    --   94.60 -61.00-150.00  182
 16  ω     27.00  70.00   0.50    0.50    --   94.60 -82.00   0.00   86
 17  ω     17.00 126.00   0.50    0.50    --   94.60 -82.00 120.00  218
 18  ω     91.00 130.00   0.50    0.50    --   94.60  82.00 120.00   78
 19  ω     84.00 115.00   0.50    0.50    --   94.60 -82.00-150.00   62
 20  ω    144.00 170.00   0.50    0.50    --   94.60  77.00 -60.00   52
 21  ω    113.00 144.00   0.50    0.50    --   94.60  77.00 150.00   62
 22  ω     75.00 102.00   0.50    0.50    --   94.60 -30.00-120.00   54
 23  ω     51.00  77.00   0.50    0.50    --   94.60 -82.00-180.00   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      -0.0374162000
_diffrn_orient_matrix_UB_12      -0.0751507000
_diffrn_orient_matrix_UB_13      0.0710811000
_diffrn_orient_matrix_UB_21      0.0319445000
_diffrn_orient_matrix_UB_22      0.0921487000
_diffrn_orient_matrix_UB_23      0.0596229000
_diffrn_orient_matrix_UB_31      -0.1733312000
_diffrn_orient_matrix_UB_32      0.0332614000
_diffrn_orient_matrix_UB_33      -0.0043427000
_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         0.728
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                3464
_reflns_number_total             3543
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 1443 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3543
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0243
_refine_ls_restrained_S_all      1.042
_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)+(0.0314P)²+0.3788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0637
_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, All O(H,H) groups
2.a Free rotating group:
 O7(H7C,H7D), O6(H6A,H6B)
2.b Ternary CH refined with riding coordinates:
 C8'(H8')
2.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C7'(H7'A,H7'B)
2.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4A), C2(H2A), C2'(H2'), C4'(H4')
2.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C9'(H9'A,H9'B,H9'C)
2.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1), O4(H4), O3(H3)
;
_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
O5 O 0.31068(13) 0.29049(8) 0.66557(7) 0.0162(2) Uani 1 1 d . . . . .
O2 O 0.42858(14) 0.62325(9) 0.48639(7) 0.0191(2) Uani 1 1 d . . . . .
H2 H 0.3415 0.6354 0.5050 0.029 Uiso 1 1 calc GR . . . .
O1 O 0.92918(13) 0.51295(9) 0.57705(7) 0.0193(2) Uani 1 1 d . . . . .
H1 H 0.9709 0.4786 0.6133 0.029 Uiso 1 1 calc GR . . . .
O4 O 0.70440(14) 0.27083(9) 0.82487(7) 0.0213(3) Uani 1 1 d . . . . .
H4 H 0.7690 0.2450 0.8558 0.032 Uiso 1 1 calc GR . . . .
O3 O 0.94032(13) 0.01256(9) 0.65384(7) 0.0201(2) Uani 1 1 d . . . . .
H3 H 0.9249 -0.0216 0.6124 0.030 Uiso 1 1 calc GR . . . .
O7 O 0.62613(15) 0.81887(10) 0.45392(7) 0.0225(3) Uani 1 1 d . . . . .
H7C H 0.5596 0.8678 0.4443 0.034 Uiso 1 1 d G . . . .
H7D H 0.5723 0.7674 0.4728 0.034 Uiso 1 1 d G . . . .
O6 O 0.45042(15) 0.59551(10) 0.19584(8) 0.0246(3) Uani 1 1 d . . . . .
H6A H 0.4463 0.5690 0.2430 0.037 Uiso 1 1 d G . . . .
H6B H 0.3660 0.6310 0.1912 0.037 Uiso 1 1 d G . . . .
C1 C 0.54054(18) 0.46093(12) 0.66339(9) 0.0148(3) Uani 1 1 d . . . . .
C3 C 0.76978(18) 0.51094(13) 0.58706(10) 0.0158(3) Uani 1 1 d . . . . .
C5' C 0.69941(19) 0.21096(12) 0.75524(9) 0.0159(3) Uani 1 1 d . . . . .
C7 C 0.47097(18) 0.40927(13) 0.73724(9) 0.0153(3) Uani 1 1 d . . . . .
H7A H 0.3774 0.4486 0.7520 0.018 Uiso 1 1 calc R . . . .
H7B H 0.5449 0.4166 0.7813 0.018 Uiso 1 1 calc R . . . .
C6 C 0.44681(19) 0.51506(12) 0.60783(9) 0.0156(3) Uani 1 1 d . . . . .
H6 H 0.3388 0.5168 0.6142 0.019 Uiso 1 1 calc R . . . .
C1' C 0.56374(19) 0.15492(13) 0.63617(9) 0.0162(3) Uani 1 1 d . . . . .
C4 C 0.67775(19) 0.56474(12) 0.53097(10) 0.0164(3) Uani 1 1 d . . . . .
H4A H 0.7227 0.5987 0.4867 0.020 Uiso 1 1 calc R . . . .
C6' C 0.56671(19) 0.21856(12) 0.70575(9) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.70235(18) 0.45869(12) 0.65253(9) 0.0157(3) Uani 1 1 d . . . . .
H2A H 0.7653 0.4222 0.6891 0.019 Uiso 1 1 calc R . . . .
C3' C 0.81735(19) 0.08215(12) 0.66663(10) 0.0172(3) Uani 1 1 d . . . . .
C5 C 0.51686(19) 0.56647(12) 0.54275(9) 0.0154(3) Uani 1 1 d . . . . .
C2' C 0.6890(2) 0.08748(13) 0.61644(9) 0.0179(3) Uani 1 1 d . . . . .
H2' H 0.6856 0.0464 0.5697 0.022 Uiso 1 1 calc R . . . .
C4' C 0.82431(19) 0.14507(13) 0.73590(10) 0.0176(3) Uani 1 1 d . . . . .
H4' H 0.9121 0.1429 0.7689 0.021 Uiso 1 1 calc R . . . .
C8' C 0.27659(19) 0.18922(13) 0.62710(10) 0.0173(3) Uani 1 1 d . . . . .
H8' H 0.2476 0.1355 0.6675 0.021 Uiso 1 1 calc R . . . .
C8 C 0.42763(18) 0.28947(12) 0.72889(9) 0.0152(3) Uani 1 1 d . . . . .
C7' C 0.4214(2) 0.15444(14) 0.58265(10) 0.0214(4) Uani 1 1 d . . . . .
H7'A H 0.4388 0.2022 0.5374 0.026 Uiso 1 1 calc R . . . .
H7'B H 0.4056 0.0828 0.5615 0.026 Uiso 1 1 calc R . . . .
C9 C 0.34998(19) 0.25162(13) 0.80710(10) 0.0191(3) Uani 1 1 d . . . . .
H9A H 0.2607 0.2958 0.8184 0.029 Uiso 1 1 calc GR . . . .
H9B H 0.4234 0.2569 0.8507 0.029 Uiso 1 1 calc GR . . . .
H9C H 0.3172 0.1785 0.8012 0.029 Uiso 1 1 calc GR . . . .
C9' C 0.1411(2) 0.21010(14) 0.57084(10) 0.0216(4) Uani 1 1 d . . . . .
H9'A H 0.0505 0.2296 0.6017 0.032 Uiso 1 1 calc GR . . . .
H9'B H 0.1192 0.1465 0.5403 0.032 Uiso 1 1 calc GR . . . .
H9'C H 0.1675 0.2675 0.5348 0.032 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
O5 C8' 1.4452(19) . ?
O5 C8 1.4503(18) . ?
O2 H2 0.8200 . ?
O2 C5 1.3948(19) . ?
O1 H1 0.8200 . ?
O1 C3 1.3734(19) . ?
O4 H4 0.8200 . ?
O4 C5' 1.3760(19) . ?
O3 H3 0.8200 . ?
O3 C3' 1.3800(19) . ?
O7 H7C 0.8501 . ?
O7 H7D 0.8501 . ?
O6 H6A 0.8496 . ?
O6 H6B 0.8500 . ?
C1 C7 1.507(2) . ?
C1 C6 1.396(2) . ?
C1 C2 1.396(2) . ?
C3 C4 1.391(2) . ?
C3 C2 1.392(2) . ?
C5' C6' 1.404(2) . ?
C5' C4' 1.385(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.546(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.391(2) . ?
C1' C6' 1.401(2) . ?
C1' C2' 1.401(2) . ?
C1' C7' 1.507(2) . ?
C4 H4A 0.9300 . ?
C4 C5 1.390(2) . ?
C6' C8 1.531(2) . ?
C2 H2A 0.9300 . ?
C3' C2' 1.379(2) . ?
C3' C4' 1.393(2) . ?
C2' H2' 0.9300 . ?
C4' H4' 0.9300 . ?
C8' H8' 0.9800 . ?
C8' C7' 1.505(2) . ?
C8' C9' 1.510(2) . ?
C8 C9 1.532(2) . ?
C7' H7'A 0.9700 . ?
C7' H7'B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9' H9'A 0.9600 . ?
C9' H9'B 0.9600 . ?
C9' H9'C 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
C8' O5 C8 116.82(11) . . ?
C5 O2 H2 109.5 . . ?
C3 O1 H1 109.5 . . ?
C5' O4 H4 109.5 . . ?
C3' O3 H3 109.5 . . ?
H7C O7 H7D 104.5 . . ?
H6A O6 H6B 104.5 . . ?
C6 C1 C7 121.15(14) . . ?
C2 C1 C7 119.20(14) . . ?
C2 C1 C6 119.59(15) . . ?
O1 C3 C4 118.15(14) . . ?
O1 C3 C2 120.94(15) . . ?
C4 C3 C2 120.90(14) . . ?
O4 C5' C6' 118.63(13) . . ?
O4 C5' C4' 119.50(14) . . ?
C4' C5' C6' 121.87(14) . . ?
C1 C7 H7A 108.3 . . ?
C1 C7 H7B 108.3 . . ?
C1 C7 C8 115.81(13) . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.22(15) . . ?
C5 C6 H6 120.4 . . ?
C6' C1' C7' 120.15(14) . . ?
C2' C1' C6' 121.27(15) . . ?
C2' C1' C7' 118.54(14) . . ?
C3 C4 H4A 120.9 . . ?
C5 C4 C3 118.25(15) . . ?
C5 C4 H4A 120.9 . . ?
C5' C6' C8 121.36(13) . . ?
C1' C6' C5' 117.26(14) . . ?
C1' C6' C8 121.32(14) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 C1 120.14(15) . . ?
C3 C2 H2A 119.9 . . ?
O3 C3' C4' 116.66(14) . . ?
C2' C3' O3 122.96(14) . . ?
C2' C3' C4' 120.31(15) . . ?
C6 C5 O2 121.41(14) . . ?
C4 C5 O2 116.70(14) . . ?
C4 C5 C6 121.89(15) . . ?
C1' C2' H2' 120.1 . . ?
C3' C2' C1' 119.77(15) . . ?
C3' C2' H2' 120.1 . . ?
C5' C4' C3' 119.50(15) . . ?
C5' C4' H4' 120.2 . . ?
C3' C4' H4' 120.3 . . ?
O5 C8' H8' 110.3 . . ?
O5 C8' C7' 107.61(13) . . ?
O5 C8' C9' 106.07(13) . . ?
C7' C8' H8' 110.3 . . ?
C7' C8' C9' 112.22(14) . . ?
C9' C8' H8' 110.3 . . ?
O5 C8 C7 102.80(11) . . ?
O5 C8 C6' 111.05(12) . . ?
O5 C8 C9 108.49(12) . . ?
C6' C8 C7 113.26(12) . . ?
C6' C8 C9 111.77(12) . . ?
C9 C8 C7 109.02(13) . . ?
C1' C7' H7'A 109.2 . . ?
C1' C7' H7'B 109.2 . . ?
C8' C7' C1' 112.02(13) . . ?
C8' C7' H7'A 109.2 . . ?
C8' C7' H7'B 109.2 . . ?
H7'A C7' H7'B 107.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8' C9' H9'A 109.5 . . ?
C8' C9' H9'B 109.5 . . ?
C8' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 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
O2 H2 O7 0.82 2.05 2.8619(17) 174.0 4_466
O1 H1 O6 0.82 1.78 2.6026(17) 176.2 2_665
O4 H4 O7 0.82 2.02 2.8168(17) 163.3 2_665
O3 H3 O2 0.82 2.07 2.8795(16) 168.3 4_556
O7 H7C O1 0.85 1.89 2.7391(16) 174.0 4_466
O6 H6A O3 0.85 1.99 2.8359(17) 172.2 4_456
O6 H6B O5 0.85 1.85 2.6943(17) 171.7 2_564

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 C8' C7' C1' 52.32(18) . . . . ?
O1 C3 C4 C5 -177.46(14) . . . . ?
O1 C3 C2 C1 177.56(14) . . . . ?
O4 C5' C6' C1' -178.69(14) . . . . ?
O4 C5' C6' C8 -1.5(2) . . . . ?
O4 C5' C4' C3' 178.17(14) . . . . ?
O3 C3' C2' C1' 175.70(14) . . . . ?
O3 C3' C4' C5' -175.42(14) . . . . ?
C1 C7 C8 O5 -61.65(16) . . . . ?
C1 C7 C8 C6' 58.25(17) . . . . ?
C1 C7 C8 C9 -176.63(13) . . . . ?
C1 C6 C5 O2 -178.83(13) . . . . ?
C1 C6 C5 C4 0.6(2) . . . . ?
C3 C4 C5 O2 178.54(13) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C5' C6' C8 O5 175.58(13) . . . . ?
C5' C6' C8 C7 60.50(18) . . . . ?
C5' C6' C8 C9 -63.11(18) . . . . ?
C7 C1 C6 C5 176.60(13) . . . . ?
C7 C1 C2 C3 -176.50(14) . . . . ?
C6 C1 C7 C8 93.41(17) . . . . ?
C6 C1 C2 C3 0.6(2) . . . . ?
C1' C6' C8 O5 -7.33(19) . . . . ?
C1' C6' C8 C7 -122.41(15) . . . . ?
C1' C6' C8 C9 113.97(16) . . . . ?
C4 C3 C2 C1 -0.9(2) . . . . ?
C6' C5' C4' C3' -1.7(2) . . . . ?
C6' C1' C2' C3' 0.8(2) . . . . ?
C6' C1' C7' C8' -22.5(2) . . . . ?
C2 C1 C7 C8 -89.58(17) . . . . ?
C2 C1 C6 C5 -0.4(2) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C2' C1' C6' C5' -0.7(2) . . . . ?
C2' C1' C6' C8 -177.92(14) . . . . ?
C2' C1' C7' C8' 154.91(14) . . . . ?
C2' C3' C4' C5' 1.7(2) . . . . ?
C4' C5' C6' C1' 1.2(2) . . . . ?
C4' C5' C6' C8 178.40(14) . . . . ?
C4' C3' C2' C1' -1.3(2) . . . . ?
C8' O5 C8 C7 163.19(12) . . . . ?
C8' O5 C8 C6' 41.77(17) . . . . ?
C8' O5 C8 C9 -81.44(15) . . . . ?
C8 O5 C8' C7' -65.59(16) . . . . ?
C8 O5 C8' C9' 174.13(12) . . . . ?
C7' C1' C6' C5' 176.66(14) . . . . ?
C7' C1' C6' C8 -0.5(2) . . . . ?
C7' C1' C2' C3' -176.63(15) . . . . ?
C9' C8' C7' C1' 168.64(14) . . . . ?

_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 1.962
_oxdiff_exptl_absorpt_empirical_full_min 0.499
####################################################################### 
# 
# 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_220301j_0m
_database_code_depnum_ccdc_archive 'CCDC 2321679'
loop_
_audit_author_name
_audit_author_address
'Hanli Ruan'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2023-12-25 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2022-03-17
_audit_creation_method           
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H45 F3 N2 O6, C1 H1 Cl3'
_chemical_formula_sum            'C41 H46 Cl3 F3 N2 O6'
_chemical_formula_weight         826.15
_chemical_absolute_configuration ad
_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 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   14.4485(12)
_cell_length_b                   8.6090(7)
_cell_length_c                   16.5929(14)
_cell_angle_alpha                90
_cell_angle_beta                 101.029(4)
_cell_angle_gamma                90
_cell_volume                     2025.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9650
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      59.03
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    1.697
_exptl_absorpt_correction_T_max  0.6750
_exptl_absorpt_correction_T_min  0.5355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 - Bruker AXS, Madison WI for PHOTON III'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1448
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            91830
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        52.499
_diffrn_reflns_theta_max         52.499
_diffrn_reflns_theta_min         2.360
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon III 28 detector'
_diffrn_detector_area_resol_mean ' 7.39 for PHOTON III'
_diffrn_detector_type            'Bruker Photon III 28'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker Photon III'
_diffrn_measurement_method       'Profile data from θ/2θ scans'
_diffrn_radiation_monochromator  'Metaljet Helios MX'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_xray_symbol    'Ga K\a'
_diffrn_source                   'METALJET liquid metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_target            Ga
_diffrn_source_type              'Sealed X-ray tube'
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                5613
_reflns_number_total             6992
_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       
'SAINT V8.40B Bruker-AXS, Madison WI for PHOTON III'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction        
'SAINT V8.40B Bruker-AXS, Madison WI for PHOTON III'
_computing_molecular_graphics    
'Bruker SHELXTL Bruker-AXS, Madison WI and local programs'
_computing_publication_material  'Bruker SHELXTL Bruker-AXS, Madison WI'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2126 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.11(3)
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         6992
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0889
_refine_ls_restrained_S_all      1.061
_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)+(0.1810P)²+0.2977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2401
_refine_ls_wR_factor_ref         0.2500
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2. Restrained distances 
 Cl2S-C1S = Cl1S-C1S = Cl3S-C1S = Cl2T-C1T = Cl3T-C1T = Cl1T-C1T 
 1.73 with sigma of 0.02 
 Cl3S-C1S \\sim Cl3T-C1T 
 with sigma of 0.02 
 Cl1S-Cl2S \\sim Cl1T-Cl2T 
 with sigma of 0.04 
 Cl1S-C1S \\sim Cl1T-C1T 
 with sigma of 0.02 
 Cl2S-C1S \\sim Cl2T-C1T 
 with sigma of 0.02 
 Cl3S-Cl1S \\sim Cl3T-Cl1T 
 with sigma of 0.04 
 Cl3S-Cl2S \\sim Cl3T-Cl2T 
 with sigma of 0.04 
3. Uiso/Uaniso restraints and constraints 
Uanis(C1S) = Uanis(C1T) 
Uanis(Cl2S) = Uanis(Cl1T) 
Uanis(Cl3S) = Uanis(Cl3T) 
Uanis(Cl1S) = Uanis(Cl2T) 
4. Others 
 Sof(C1T)=Sof(H1T)=Sof(Cl1T)=Sof(Cl2T)=Sof(Cl3T)=1-FVAR(1) 
 Sof(C1S)=Sof(H1S)=Sof(Cl1S)=Sof(Cl2S)=Sof(Cl3S)=FVAR(1) 
5.a Ternary CH refined with riding coordinates: 
 C3(H3), C4(H4), C5(H5), C8(H8), C16(H16), C18(H18), C19(H19), C1S(H1S), 
 C1T(H1T) 
5.b Secondary CH2 refined with riding coordinates: 
 C10(H10A,H10B), C15(H15A,H15B), C17(H17A,H17B), C20(H20A,H20B) 
5.c Aromatic/amide H refined with riding coordinates: 
 C2"(H2"), C2'(H2'), C3"(H3"), C4"(H4"), C5"(H5"), C5'(H5'), C6"(H6"), 
 C6'(H6'), C7(H7), C7'(H7'), C8'(H8'), C13(H13), C14(H14), N1'(H1'), N2(H2) 
5.d Idealised Me refined as rotating group: 
 C9"(H9"A,H9"B,H9"C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C22(H22A,H22B, 
 H22C), C23(H23A,H23B,H23C) 
;
_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
C1 C 0.4927(5) 0.1571(8) 0.3240(4) 0.0388(15) Uani 1 1 d . . . . .
C1" C 0.9138(5) 0.7777(7) 0.1341(4) 0.0396(15) Uani 1 1 d . . . . .
C2" C 0.9564(5) 0.9095(9) 0.1083(5) 0.0446(16) Uani 1 1 d . . . . .
H2" H 0.980866 0.905649 0.059164 0.053 Uiso 1 1 calc R U . . .
C2' C 0.4472(6) 0.6782(8) 0.3686(4) 0.0472(17) Uani 1 1 d . . . . .
H2' H 0.385265 0.714809 0.347753 0.057 Uiso 1 1 calc R U . . .
C3 C 0.3809(5) 0.2844(8) 0.3859(5) 0.0442(16) Uani 1 1 d . . . . .
H3 H 0.329354 0.224426 0.404167 0.053 Uiso 1 1 calc R U . . .
C3" C 0.9633(5) 1.0452(8) 0.1533(5) 0.0482(18) Uani 1 1 d . . . . .
H3" H 0.991341 1.134699 0.134514 0.058 Uiso 1 1 calc R U . . .
C3' C 0.4691(5) 0.5445(8) 0.4136(4) 0.0424(16) Uani 1 1 d . . . . .
C4 C 0.3526(5) 0.3140(8) 0.2922(4) 0.0452(17) Uani 1 1 d . . . . .
H4 H 0.346530 0.428667 0.283069 0.054 Uiso 1 1 calc R U . . .
C4" C 0.9289(6) 1.0509(8) 0.2263(5) 0.0484(17) Uani 1 1 d . . . . .
H4" H 0.934331 1.143409 0.258042 0.058 Uiso 1 1 calc R U . . .
C4' C 0.5699(6) 0.5350(8) 0.4322(4) 0.0442(16) Uani 1 1 d . . . . .
C5 C 0.2557(6) 0.2362(10) 0.2537(5) 0.0537(19) Uani 1 1 d . . . . .
H5 H 0.237708 0.280011 0.197030 0.064 Uiso 1 1 calc R U . . .
C5" C 0.8876(6) 0.9220(9) 0.2517(5) 0.0516(19) Uani 1 1 d . . . . .
H5" H 0.863813 0.926544 0.301207 0.062 Uiso 1 1 calc R U . . .
C5' C 0.6369(6) 0.4327(10) 0.4768(5) 0.053(2) Uani 1 1 d . . . . .
H5' H 0.617762 0.342495 0.502262 0.064 Uiso 1 1 calc R U . . .
C6 C 0.2712(6) 0.0629(10) 0.2426(5) 0.0543(19) Uani 1 1 d . . . . .
C6" C 0.8790(6) 0.7826(8) 0.2065(4) 0.0449(16) Uani 1 1 d . . . . .
H6" H 0.850124 0.693866 0.225136 0.054 Uiso 1 1 calc R U . . .
C6' C 0.7332(7) 0.4683(13) 0.4824(6) 0.068(2) Uani 1 1 d . . . . .
H6' H 0.778788 0.400393 0.512773 0.081 Uiso 1 1 calc R U . . .
C7 C 0.3393(6) 0.0292(9) 0.2030(5) 0.0535(19) Uani 1 1 d . . . . .
H7 H 0.350426 -0.076362 0.191016 0.064 Uiso 1 1 calc R U . . .
C7" C 0.9092(6) 0.6282(8) 0.0838(4) 0.0424(16) Uani 1 1 d . . . . .
C7' C 0.7637(7) 0.5941(15) 0.4468(6) 0.074(3) Uani 1 1 d . . . . .
H7' H 0.829412 0.610772 0.450958 0.089 Uiso 1 1 calc R U . . .
C8 C 0.3993(6) 0.1526(8) 0.1763(4) 0.0473(17) Uani 1 1 d . . . . .
H8 H 0.356310 0.220091 0.136677 0.057 Uiso 1 1 calc R U . . .
C8" C 0.8483(6) 0.6487(8) -0.0021(4) 0.0484(18) Uani 1 1 d . . . . .
C8' C 0.7002(7) 0.6990(11) 0.4044(5) 0.062(2) Uani 1 1 d . . . . .
H8' H 0.721163 0.790532 0.381399 0.074 Uiso 1 1 calc R U . . .
C9 C 0.4363(5) 0.2559(7) 0.2553(4) 0.0412(16) Uani 1 1 d . . . . .
C9" C 1.0791(6) 0.5929(10) 0.1306(5) 0.0524(18) Uani 1 1 d . . . . .
H9"A H 1.090962 0.701507 0.147133 0.079 Uiso 1 1 calc R U . . .
H9"B H 1.134074 0.550971 0.111371 0.079 Uiso 1 1 calc R U . . .
H9"C H 1.067687 0.532153 0.177690 0.079 Uiso 1 1 calc R U . . .
C9' C 0.6048(6) 0.6669(9) 0.3964(4) 0.0499(19) Uani 1 1 d . . . . .
C10 C 0.3995(6) 0.4348(8) 0.4382(4) 0.0441(17) Uani 1 1 d . . . . .
H10A H 0.338909 0.490243 0.435078 0.053 Uiso 1 1 calc R U . . .
H10B H 0.422129 0.404815 0.496203 0.053 Uiso 1 1 calc R U . . .
C10" C 0.8719(5) 0.4941(7) 0.1305(4) 0.0410(16) Uani 1 1 d . . . . .
C11 C 0.1759(6) 0.2792(12) 0.2974(6) 0.065(2) Uani 1 1 d . . . . .
H11A H 0.115618 0.246007 0.264175 0.097 Uiso 1 1 calc R U . . .
H11B H 0.175157 0.391964 0.305363 0.097 Uiso 1 1 calc R U . . .
H11C H 0.185429 0.227294 0.350955 0.097 Uiso 1 1 calc R U . . .
C12 C 0.2090(7) -0.0540(12) 0.2731(6) 0.071(3) Uani 1 1 d . . . . .
H12A H 0.230691 -0.159041 0.263629 0.106 Uiso 1 1 calc R U . . .
H12B H 0.143887 -0.040738 0.243661 0.106 Uiso 1 1 calc R U . . .
H12C H 0.211677 -0.038474 0.332049 0.106 Uiso 1 1 calc R U . . .
C13 C 0.4749(6) 0.0949(9) 0.1320(5) 0.0478(18) Uani 1 1 d . . . . .
H13 H 0.508937 0.004474 0.152741 0.057 Uiso 1 1 calc R U . . .
C14 C 0.4967(6) 0.1612(9) 0.0667(4) 0.0476(18) Uani 1 1 d . . . . .
H14 H 0.461515 0.250637 0.045896 0.057 Uiso 1 1 calc R U . . .
C15 C 0.5717(6) 0.1087(8) 0.0223(5) 0.0486(18) Uani 1 1 d . . . . .
H15A H 0.543605 0.096644 -0.036595 0.058 Uiso 1 1 calc R U . . .
H15B H 0.594375 0.005249 0.043546 0.058 Uiso 1 1 calc R U . . .
C16 C 0.6570(6) 0.2190(9) 0.0303(4) 0.0456(17) Uani 1 1 d . . . . .
H16 H 0.633094 0.326767 0.016784 0.055 Uiso 1 1 calc R U . . .
C17 C 0.7166(6) 0.2192(8) 0.1184(4) 0.0446(16) Uani 1 1 d . . . . .
H17A H 0.685711 0.148688 0.152302 0.053 Uiso 1 1 calc R U . . .
H17B H 0.778946 0.173933 0.115889 0.053 Uiso 1 1 calc R U . . .
C18 C 0.7331(5) 0.3738(8) 0.1630(4) 0.0403(16) Uani 1 1 d . . . . .
H18 H 0.777013 0.356737 0.216651 0.048 Uiso 1 1 calc R U . . .
C19 C 0.6469(5) 0.4596(7) 0.1790(4) 0.0394(15) Uani 1 1 d . . . . .
H19 H 0.601072 0.474365 0.126154 0.047 Uiso 1 1 calc R U . . .
C20 C 0.6004(5) 0.3674(7) 0.2389(4) 0.0397(15) Uani 1 1 d . . . . .
H20A H 0.614816 0.255829 0.233707 0.048 Uiso 1 1 calc R U . . .
H20B H 0.628436 0.399930 0.295589 0.048 Uiso 1 1 calc R U . . .
C21 C 0.4948(5) 0.3875(8) 0.2259(4) 0.0380(15) Uani 1 1 d . . . . .
C22 C 0.7190(7) 0.1718(10) -0.0312(5) 0.056(2) Uani 1 1 d . . . . .
H22A H 0.737958 0.062989 -0.022135 0.085 Uiso 1 1 calc R U . . .
H22B H 0.775223 0.237865 -0.023366 0.085 Uiso 1 1 calc R U . . .
H22C H 0.683253 0.184572 -0.087254 0.085 Uiso 1 1 calc R U . . .
C23 C 0.6334(7) 0.7344(9) 0.1694(5) 0.057(2) Uani 1 1 d . . . . .
H23A H 0.658085 0.742873 0.118541 0.086 Uiso 1 1 calc R U . . .
H23B H 0.648156 0.829480 0.201804 0.086 Uiso 1 1 calc R U . . .
H23C H 0.564910 0.719986 0.156116 0.086 Uiso 1 1 calc R U . . .
F1 F 0.7629(3) 0.7089(5) 0.0015(3) 0.0548(11) Uani 1 1 d . . . . .
F2 F 0.8347(4) 0.5156(5) -0.0419(2) 0.0585(12) Uani 1 1 d . . . . .
F3 F 0.8877(3) 0.7456(5) -0.0483(2) 0.0568(12) Uani 1 1 d . . . . .
N1' N 0.5290(6) 0.7506(7) 0.3586(4) 0.0550(17) Uani 1 1 d . . . . .
H1' H 0.531908 0.838031 0.331696 0.066 Uiso 1 1 calc R U . . .
N2 N 0.4631(5) 0.1853(7) 0.3925(3) 0.0443(14) Uani 1 1 d . . . . .
H2 H 0.491622 0.146371 0.439775 0.053 Uiso 1 1 calc R U . . .
O1 O 0.5563(4) 0.0643(5) 0.3157(3) 0.0467(12) Uani 1 1 d . . . . .
O2 O 0.4546(4) 0.4983(6) 0.1907(3) 0.0482(12) Uani 1 1 d . . . . .
O3 O 0.6749(4) 0.6074(5) 0.2148(3) 0.0434(12) Uani 1 1 d . . . . .
O4 O 0.7779(4) 0.4818(5) 0.1132(3) 0.0419(11) Uani 1 1 d . . . . .
O5 O 0.9235(4) 0.4100(6) 0.1771(4) 0.0565(14) Uani 1 1 d . . . . .
O6 O 0.9976(4) 0.5843(6) 0.0654(3) 0.0460(12) Uani 1 1 d . . . . .
C1S C 0.0574(11) 0.631(2) 0.5056(10) 0.117(7) Uani 0.765(5) 1 d D . P A 1
H1S H 0.009857 0.547581 0.509002 0.140 Uiso 0.765(5) 1 calc R U P A 1
Cl1S Cl 0.0459(5) 0.7739(8) 0.5796(4) 0.135(2) Uani 0.765(5) 1 d D . P A 1
Cl2S Cl 0.1663(4) 0.5449(7) 0.5227(4) 0.123(2) Uani 0.765(5) 1 d D . P A 1
Cl3S Cl 0.0300(4) 0.7117(9) 0.4070(3) 0.130(2) Uani 0.765(5) 1 d D . P A 1
C1T C 0.1114(17) 0.617(9) 0.5122(16) 0.117(7) Uani 0.235(5) 1 d D . P A 2
H1T H 0.101997 0.502844 0.504968 0.140 Uiso 0.235(5) 1 calc R U P A 2
Cl1T Cl 0.2250(12) 0.599(2) 0.5749(12) 0.123(2) Uani 0.235(5) 1 d D . P A 2
Cl2T Cl 0.0136(16) 0.642(3) 0.5572(13) 0.135(2) Uani 0.235(5) 1 d D . P A 2
Cl3T Cl 0.0990(14) 0.654(3) 0.4064(11) 0.130(2) Uani 0.235(5) 1 d D . P A 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C9 1.526(9) . ?
C1 N2 1.311(9) . ?
C1 O1 1.245(9) . ?
C1" C2" 1.396(10) . ?
C1" C6" 1.388(11) . ?
C1" C7" 1.529(9) . ?
C2" H2" 0.9500 . ?
C2" C3" 1.379(11) . ?
C2' H2' 0.9500 . ?
C2' C3' 1.376(10) . ?
C2' N1' 1.374(11) . ?
C3 H3 1.0000 . ?
C3 C4 1.550(10) . ?
C3 C10 1.553(10) . ?
C3 N2 1.450(10) . ?
C3" H3" 0.9500 . ?
C3" C4" 1.396(12) . ?
C3' C4' 1.432(11) . ?
C3' C10 1.492(10) . ?
C4 H4 1.0000 . ?
C4 C5 1.573(11) . ?
C4 C9 1.540(11) . ?
C4" H4" 0.9500 . ?
C4" C5" 1.364(11) . ?
C4' C5' 1.409(12) . ?
C4' C9' 1.417(10) . ?
C5 H5 1.0000 . ?
C5 C6 1.525(13) . ?
C5 C11 1.521(14) . ?
C5" H5" 0.9500 . ?
C5" C6" 1.408(10) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.411(14) . ?
C6 C7 1.316(12) . ?
C6 C12 1.501(13) . ?
C6" H6" 0.9500 . ?
C6' H6' 0.9500 . ?
C6' C7' 1.347(16) . ?
C7 H7 0.9500 . ?
C7 C8 1.491(12) . ?
C7" C8" 1.535(10) . ?
C7" C10" 1.543(10) . ?
C7" O6 1.420(9) . ?
C7' H7' 0.9500 . ?
C7' C8' 1.381(16) . ?
C8 H8 1.0000 . ?
C8 C9 1.589(9) . ?
C8 C13 1.512(12) . ?
C8" F1 1.350(10) . ?
C8" F2 1.318(9) . ?
C8" F3 1.332(8) . ?
C8' H8' 0.9500 . ?
C8' C9' 1.387(13) . ?
C9 C21 1.547(9) . ?
C9" H9"A 0.9800 . ?
C9" H9"B 0.9800 . ?
C9" H9"C 0.9800 . ?
C9" O6 1.441(10) . ?
C9' N1' 1.360(12) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10" O4 1.337(9) . ?
C10" O5 1.208(9) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.315(11) . ?
C14 H14 0.9500 . ?
C14 C15 1.492(12) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.541(11) . ?
C16 H16 1.0000 . ?
C16 C17 1.548(10) . ?
C16 C22 1.535(11) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.519(10) . ?
C18 H18 1.0000 . ?
C18 C19 1.514(10) . ?
C18 O4 1.474(8) . ?
C19 H19 1.0000 . ?
C19 C20 1.525(10) . ?
C19 O3 1.430(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.510(10) . ?
C21 O2 1.208(8) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 O3 1.396(9) . ?
N1' H1' 0.8800 . ?
N2 H2 0.8800 . ?
C1S H1S 1.0000 . ?
C1S Cl1S 1.771(17) . ?
C1S Cl2S 1.712(15) . ?
C1S Cl3S 1.753(15) . ?
C1T H1T 1.0000 . ?
C1T Cl1T 1.78(2) . ?
C1T Cl2T 1.73(2) . ?
C1T Cl3T 1.76(2) . ?

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
N2 C1 C9 109.1(6) . . ?
O1 C1 C9 125.1(6) . . ?
O1 C1 N2 125.7(6) . . ?
C2" C1" C7" 119.5(6) . . ?
C6" C1" C2" 119.6(6) . . ?
C6" C1" C7" 120.8(6) . . ?
C1" C2" H2" 119.6 . . ?
C3" C2" C1" 120.9(7) . . ?
C3" C2" H2" 119.6 . . ?
C3' C2' H2' 125.3 . . ?
N1' C2' H2' 125.3 . . ?
N1' C2' C3' 109.4(7) . . ?
C4 C3 H3 108.7 . . ?
C4 C3 C10 114.1(6) . . ?
C10 C3 H3 108.7 . . ?
N2 C3 H3 108.7 . . ?
N2 C3 C4 103.2(6) . . ?
N2 C3 C10 113.3(6) . . ?
C2" C3" H3" 120.1 . . ?
C2" C3" C4" 119.8(7) . . ?
C4" C3" H3" 120.1 . . ?
C2' C3' C4' 106.4(7) . . ?
C2' C3' C10 125.5(7) . . ?
C4' C3' C10 128.0(6) . . ?
C3 C4 H4 108.2 . . ?
C3 C4 C5 112.4(6) . . ?
C5 C4 H4 108.2 . . ?
C9 C4 C3 105.6(6) . . ?
C9 C4 H4 108.2 . . ?
C9 C4 C5 113.9(6) . . ?
C3" C4" H4" 120.3 . . ?
C5" C4" C3" 119.3(7) . . ?
C5" C4" H4" 120.3 . . ?
C5' C4' C3' 135.7(7) . . ?
C5' C4' C9' 117.2(7) . . ?
C9' C4' C3' 107.0(7) . . ?
C4 C5 H5 105.8 . . ?
C6 C5 C4 109.0(7) . . ?
C6 C5 H5 105.8 . . ?
C11 C5 C4 113.6(7) . . ?
C11 C5 H5 105.8 . . ?
C11 C5 C6 116.0(8) . . ?
C4" C5" H5" 119.1 . . ?
C4" C5" C6" 121.9(7) . . ?
C6" C5" H5" 119.1 . . ?
C4' C5' H5' 121.0 . . ?
C4' C5' C6' 117.9(8) . . ?
C6' C5' H5' 121.0 . . ?
C7 C6 C5 114.7(8) . . ?
C7 C6 C12 125.0(9) . . ?
C12 C6 C5 120.2(8) . . ?
C1" C6" C5" 118.5(7) . . ?
C1" C6" H6" 120.8 . . ?
C5" C6" H6" 120.8 . . ?
C5' C6' H6' 118.4 . . ?
C7' C6' C5' 123.2(10) . . ?
C7' C6' H6' 118.4 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.5(8) . . ?
C8 C7 H7 119.2 . . ?
C1" C7" C8" 111.6(6) . . ?
C1" C7" C10" 109.8(5) . . ?
C8" C7" C10" 111.0(6) . . ?
O6 C7" C1" 113.2(6) . . ?
O6 C7" C8" 102.1(6) . . ?
O6 C7" C10" 108.9(6) . . ?
C6' C7' H7' 119.7 . . ?
C6' C7' C8' 120.6(9) . . ?
C8' C7' H7' 119.7 . . ?
C7 C8 H8 106.6 . . ?
C7 C8 C9 106.1(6) . . ?
C7 C8 C13 115.2(6) . . ?
C9 C8 H8 106.6 . . ?
C13 C8 H8 106.6 . . ?
C13 C8 C9 115.1(6) . . ?
F1 C8" C7" 111.7(6) . . ?
F2 C8" C7" 111.7(6) . . ?
F2 C8" F1 107.8(6) . . ?
F2 C8" F3 107.2(6) . . ?
F3 C8" C7" 112.0(6) . . ?
F3 C8" F1 106.2(6) . . ?
C7' C8' H8' 121.0 . . ?
C7' C8' C9' 118.0(9) . . ?
C9' C8' H8' 121.0 . . ?
C1 C9 C4 103.4(5) . . ?
C1 C9 C8 110.6(5) . . ?
C1 C9 C21 113.4(6) . . ?
C4 C9 C8 110.1(6) . . ?
C4 C9 C21 113.9(5) . . ?
C21 C9 C8 105.5(5) . . ?
H9"A C9" H9"B 109.5 . . ?
H9"A C9" H9"C 109.5 . . ?
H9"B C9" H9"C 109.5 . . ?
O6 C9" H9"A 109.5 . . ?
O6 C9" H9"B 109.5 . . ?
O6 C9" H9"C 109.5 . . ?
C8' C9' C4' 123.1(8) . . ?
N1' C9' C4' 107.4(7) . . ?
N1' C9' C8' 129.5(8) . . ?
C3 C10 H10A 108.4 . . ?
C3 C10 H10B 108.4 . . ?
C3' C10 C3 115.4(6) . . ?
C3' C10 H10A 108.4 . . ?
C3' C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
O4 C10" C7" 112.9(6) . . ?
O5 C10" C7" 122.5(7) . . ?
O5 C10" O4 124.5(6) . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13 117.7 . . ?
C14 C13 C8 124.6(7) . . ?
C14 C13 H13 117.7 . . ?
C13 C14 H14 117.1 . . ?
C13 C14 C15 125.9(7) . . ?
C15 C14 H14 117.1 . . ?
C14 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
C14 C15 C16 114.5(6) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C15 C16 H16 108.5 . . ?
C15 C16 C17 111.9(6) . . ?
C17 C16 H16 108.5 . . ?
C22 C16 C15 109.8(6) . . ?
C22 C16 H16 108.5 . . ?
C22 C16 C17 109.7(7) . . ?
C16 C17 H17A 107.8 . . ?
C16 C17 H17B 107.8 . . ?
H17A C17 H17B 107.2 . . ?
C18 C17 C16 117.9(6) . . ?
C18 C17 H17A 107.8 . . ?
C18 C17 H17B 107.8 . . ?
C17 C18 H18 108.6 . . ?
C19 C18 C17 117.0(6) . . ?
C19 C18 H18 108.6 . . ?
O4 C18 C17 108.9(5) . . ?
O4 C18 H18 108.6 . . ?
O4 C18 C19 104.7(5) . . ?
C18 C19 H19 109.8 . . ?
C18 C19 C20 109.8(5) . . ?
C20 C19 H19 109.8 . . ?
O3 C19 C18 109.3(6) . . ?
O3 C19 H19 109.8 . . ?
O3 C19 C20 108.5(5) . . ?
C19 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 C19 113.9(6) . . ?
C21 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C20 C21 C9 118.0(6) . . ?
O2 C21 C9 119.3(6) . . ?
O2 C21 C20 122.6(6) . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
C2' N1' H1' 125.1 . . ?
C9' N1' C2' 109.8(6) . . ?
C9' N1' H1' 125.1 . . ?
C1 N2 C3 116.2(6) . . ?
C1 N2 H2 121.9 . . ?
C3 N2 H2 121.9 . . ?
C23 O3 C19 114.5(5) . . ?
C10" O4 C18 117.9(5) . . ?
C7" O6 C9" 117.6(6) . . ?
Cl1S C1S H1S 107.6 . . ?
Cl2S C1S H1S 107.6 . . ?
Cl2S C1S Cl1S 113.0(10) . . ?
Cl2S C1S Cl3S 111.3(8) . . ?
Cl3S C1S H1S 107.6 . . ?
Cl3S C1S Cl1S 109.6(9) . . ?
Cl1T C1T H1T 93.9 . . ?
Cl2T C1T H1T 93.9 . . ?
Cl2T C1T Cl1T 119.9(17) . . ?
Cl2T C1T Cl3T 118.2(17) . . ?
Cl3T C1T H1T 93.9 . . ?
Cl3T C1T Cl1T 120.5(16) . . ?

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
C1 C9 C21 C20 24.4(8) . . . . ?
C1 C9 C21 O2 -158.6(6) . . . . ?
C1" C2" C3" C4" 1.2(11) . . . . ?
C1" C7" C8" F1 -51.4(8) . . . . ?
C1" C7" C8" F2 -172.3(6) . . . . ?
C1" C7" C8" F3 67.5(8) . . . . ?
C1" C7" C10" O4 89.2(7) . . . . ?
C1" C7" C10" O5 -91.2(8) . . . . ?
C1" C7" O6 C9" 44.5(8) . . . . ?
C2" C1" C6" C5" 0.3(11) . . . . ?
C2" C1" C7" C8" -64.2(9) . . . . ?
C2" C1" C7" C10" 172.2(6) . . . . ?
C2" C1" C7" O6 50.3(9) . . . . ?
C2" C3" C4" C5" -1.0(12) . . . . ?
C2' C3' C4' C5' 178.0(8) . . . . ?
C2' C3' C4' C9' -0.1(7) . . . . ?
C2' C3' C10 C3 101.6(8) . . . . ?
C3 C4 C5 C6 -78.1(8) . . . . ?
C3 C4 C5 C11 52.8(9) . . . . ?
C3 C4 C9 C1 15.5(7) . . . . ?
C3 C4 C9 C8 133.7(6) . . . . ?
C3 C4 C9 C21 -108.0(6) . . . . ?
C3" C4" C5" C6" 0.5(13) . . . . ?
C3' C2' N1' C9' -0.1(8) . . . . ?
C3' C4' C5' C6' -178.1(8) . . . . ?
C3' C4' C9' C8' 177.7(7) . . . . ?
C3' C4' C9' N1' 0.1(7) . . . . ?
C4 C3 C10 C3' -53.6(9) . . . . ?
C4 C3 N2 C1 3.7(8) . . . . ?
C4 C5 C6 C7 -51.8(9) . . . . ?
C4 C5 C6 C12 130.3(8) . . . . ?
C4 C9 C21 C20 142.4(6) . . . . ?
C4 C9 C21 O2 -40.7(8) . . . . ?
C4" C5" C6" C1" -0.1(13) . . . . ?
C4' C3' C10 C3 -79.4(9) . . . . ?
C4' C5' C6' C7' -0.5(13) . . . . ?
C4' C9' N1' C2' 0.0(8) . . . . ?
C5 C4 C9 C1 -108.3(6) . . . . ?
C5 C4 C9 C8 9.9(8) . . . . ?
C5 C4 C9 C21 128.2(6) . . . . ?
C5 C6 C7 C8 3.6(11) . . . . ?
C5' C4' C9' C8' -0.9(10) . . . . ?
C5' C4' C9' N1' -178.5(6) . . . . ?
C5' C6' C7' C8' 2.2(14) . . . . ?
C6 C7 C8 C9 51.0(9) . . . . ?
C6 C7 C8 C13 179.6(7) . . . . ?
C6" C1" C2" C3" -0.8(11) . . . . ?
C6" C1" C7" C8" 117.9(7) . . . . ?
C6" C1" C7" C10" -5.7(10) . . . . ?
C6" C1" C7" O6 -127.6(7) . . . . ?
C6' C7' C8' C9' -3.0(13) . . . . ?
C7 C8 C9 C1 59.4(8) . . . . ?
C7 C8 C9 C4 -54.2(7) . . . . ?
C7 C8 C9 C21 -177.6(6) . . . . ?
C7 C8 C13 C14 138.4(8) . . . . ?
C7" C1" C2" C3" -178.7(7) . . . . ?
C7" C1" C6" C5" 178.2(7) . . . . ?
C7" C10" O4 C18 -171.0(5) . . . . ?
C7' C8' C9' C4' 2.4(11) . . . . ?
C7' C8' C9' N1' 179.5(8) . . . . ?
C8 C9 C21 C20 -96.7(7) . . . . ?
C8 C9 C21 O2 80.2(7) . . . . ?
C8 C13 C14 C15 179.0(6) . . . . ?
C8" C7" C10" O4 -34.6(8) . . . . ?
C8" C7" C10" O5 145.0(7) . . . . ?
C8" C7" O6 C9" 164.6(6) . . . . ?
C8' C9' N1' C2' -177.4(8) . . . . ?
C9 C1 N2 C3 6.7(8) . . . . ?
C9 C4 C5 C6 41.9(9) . . . . ?
C9 C4 C5 C11 172.9(7) . . . . ?
C9 C8 C13 C14 -97.7(8) . . . . ?
C9' C4' C5' C6' -0.1(10) . . . . ?
C10 C3 C4 C5 -124.0(7) . . . . ?
C10 C3 C4 C9 111.2(7) . . . . ?
C10 C3 N2 C1 -120.1(7) . . . . ?
C10 C3' C4' C5' -1.1(13) . . . . ?
C10 C3' C4' C9' -179.3(6) . . . . ?
C10" C7" C8" F1 71.4(7) . . . . ?
C10" C7" C8" F2 -49.5(8) . . . . ?
C10" C7" C8" F3 -169.7(6) . . . . ?
C10" C7" O6 C9" -77.9(7) . . . . ?
C11 C5 C6 C7 178.5(7) . . . . ?
C11 C5 C6 C12 0.7(12) . . . . ?
C12 C6 C7 C8 -178.6(8) . . . . ?
C13 C8 C9 C1 -69.2(8) . . . . ?
C13 C8 C9 C4 177.1(6) . . . . ?
C13 C8 C9 C21 53.8(7) . . . . ?
C13 C14 C15 C16 -111.3(8) . . . . ?
C14 C15 C16 C17 69.5(8) . . . . ?
C14 C15 C16 C22 -168.4(7) . . . . ?
C15 C16 C17 C18 -123.7(7) . . . . ?
C16 C17 C18 C19 61.5(8) . . . . ?
C16 C17 C18 O4 -56.9(8) . . . . ?
C17 C18 C19 C20 66.1(7) . . . . ?
C17 C18 C19 O3 -175.0(5) . . . . ?
C17 C18 O4 C10" -95.5(6) . . . . ?
C18 C19 C20 C21 -148.9(5) . . . . ?
C18 C19 O3 C23 120.3(7) . . . . ?
C19 C18 O4 C10" 138.5(5) . . . . ?
C19 C20 C21 C9 155.0(6) . . . . ?
C19 C20 C21 O2 -21.9(9) . . . . ?
C20 C19 O3 C23 -119.9(7) . . . . ?
C22 C16 C17 C18 114.1(7) . . . . ?
N1' C2' C3' C4' 0.1(7) . . . . ?
N1' C2' C3' C10 179.3(6) . . . . ?
N2 C1 C9 C4 -14.0(7) . . . . ?
N2 C1 C9 C8 -131.8(6) . . . . ?
N2 C1 C9 C21 109.9(7) . . . . ?
N2 C3 C4 C5 112.6(6) . . . . ?
N2 C3 C4 C9 -12.1(7) . . . . ?
N2 C3 C10 C3' 64.1(8) . . . . ?
O1 C1 C9 C4 165.8(6) . . . . ?
O1 C1 C9 C8 48.0(9) . . . . ?
O1 C1 C9 C21 -70.3(8) . . . . ?
O1 C1 N2 C3 -173.1(6) . . . . ?
O3 C19 C20 C21 91.8(7) . . . . ?
O4 C18 C19 C20 -173.2(5) . . . . ?
O4 C18 C19 O3 -54.3(6) . . . . ?
O5 C10" O4 C18 9.4(9) . . . . ?
O6 C7" C8" F1 -172.7(5) . . . . ?
O6 C7" C8" F2 66.5(7) . . . . ?
O6 C7" C8" F3 -53.7(7) . . . . ?
O6 C7" C10" O4 -146.2(5) . . . . ?
O6 C7" C10" O5 33.3(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_220225a_0m
_database_code_depnum_ccdc_archive 'CCDC 2321678'
loop_
_audit_author_name
_audit_author_address
'Hanli Ruan'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2024-01-30 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2024-01-30
_audit_creation_method           
; 
Olex2 1.5 
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 O5, 2(H2 O)'
_chemical_formula_sum            'C18 H24 O7'
_chemical_formula_weight         352.37
_chemical_absolute_configuration ad
_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 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.8560(6)
_cell_length_b                   9.6968(7)
_cell_length_c                   12.0012(9)
_cell_angle_alpha                70.9980(10)
_cell_angle_beta                 85.0370(10)
_cell_angle_gamma                87.5120(10)
_cell_volume                     861.06(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9117
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.25
_cell_measurement_theta_min      3.40
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  0.3859
_exptl_absorpt_correction_T_min  0.2666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick,2014'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_av_unetI/netI     0.1307
_diffrn_reflns_Laue_measured_fraction_full 0.890
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            47380
_diffrn_reflns_point_group_measured_fraction_full 0.841
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         72.365
_diffrn_reflns_theta_min         3.399
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon III 28 detector'
_diffrn_detector_area_resol_mean ' 7.39 for PHOTON III'
_diffrn_detector_type            'Bruker Photon III 28'
_diffrn_measured_fraction_theta_full 0.890
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Metaljet Helios MX'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_xray_symbol    'Ga K\a'
_diffrn_source                   'METALJET liquid metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.24972149999999999
_diffrn_source_target            Ga
_diffrn_source_type              'Sealed X-ray tube'
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.792
_reflns_Friedel_fraction_max     0.809
_reflns_number_gt                8760
_reflns_number_total             8985
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XM  (Sheldrick, 2008)'
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.122
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3754 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.19(18)
_refine_ls_extinction_coef       0.81(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         8985
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0778
_refine_ls_restrained_S_all      1.088
_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)+(0.1849P)²+0.0419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2146
_refine_ls_wR_factor_ref         0.2382
_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, All O(H,H) groups 
2.a Riding coordinates: 
 O1(H1), O1'(H1'), O2(H2), O2'(H2'), O1A(H1A), O1B(H1B), O2A(H2AA), O2B(H2B), 
 O1W(H1WA,H1WB), O2W(H2WA,H2WB), O3W(H3WA,H3WB), O4W(H4WA,H4WB) 
2.b Ternary CH refined with riding coordinates: 
 C8'(H8'), C8B(H8B) 
2.c Secondary CH2 refined with riding coordinates: 
 C7(H7A,H7B), C7'(H7'A,H7'B), C7A(H7AA,H7AB), C7B(H7BA,H7BB) 
2.d Aromatic/amide H refined with riding coordinates: 
 C2(H2A), C2'(H2'A), C4(H4), C4'(H4'), C6(H6), C2A(H2AB), C2B(H2BA), C4A(H4A), 
 C4B(H4B), C6A(H6A) 
2.e Idealised Me refined as rotating group: 
 C9(H9A,H9B,H9C), C9'(H9'A,H9'B,H9'C), C9A(H9AA,H9AB,H9AC), C9B(H9BA,H9BB,H9BC) 
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8724(3) 0.1888(3) 1.0415(2) 0.0224(5) Uani 1 1 d . . . . .
H1 H 0.810402 0.116011 1.073540 0.034 Uiso 1 1 d R U . . .
O1' O 1.3331(3) 0.9881(2) 0.21171(19) 0.0196(5) Uani 1 1 d . . . . .
H1' H 1.285654 1.065090 0.170826 0.029 Uiso 1 1 d R U . . .
O2 O 0.3517(3) 0.4146(3) 0.8763(2) 0.0203(5) Uani 1 1 d . . . . .
H2 H 0.311147 0.434817 0.936381 0.030 Uiso 1 1 d R U . . .
O2' O 1.2877(3) 0.6370(3) 0.5958(2) 0.0198(5) Uani 1 1 d . . . . .
H2' H 1.280075 0.561074 0.577537 0.030 Uiso 1 1 d R U . . .
O3' O 0.8045(3) 0.8243(2) 0.67101(19) 0.0167(4) Uani 1 1 d . . . . .
C1 C 0.8004(4) 0.4927(3) 0.7735(2) 0.0153(5) Uani 1 1 d . . . . .
C1' C 0.9866(4) 0.9235(3) 0.4508(2) 0.0156(5) Uani 1 1 d . . . . .
C2 C 0.8813(4) 0.3862(3) 0.8625(3) 0.0171(5) Uani 1 1 d . . . . .
H2A H 1.002486 0.378630 0.858011 0.020 Uiso 1 1 calc R U . . .
C2' C 1.0773(4) 0.9853(3) 0.3404(3) 0.0167(5) Uani 1 1 d . . . . .
H2'A H 1.028070 1.063816 0.281324 0.020 Uiso 1 1 calc R U . . .
C3 C 0.7864(4) 0.2912(3) 0.9576(3) 0.0169(5) Uani 1 1 d . . . . .
C3' C 1.2385(4) 0.9317(3) 0.3178(3) 0.0160(5) Uani 1 1 d . . . . .
C4 C 0.6073(4) 0.2978(3) 0.9648(3) 0.0163(5) Uani 1 1 d . . . . .
H4 H 0.541897 0.231177 1.028297 0.020 Uiso 1 1 calc R U . . .
C4' C 1.3097(4) 0.8150(3) 0.4036(3) 0.0160(5) Uani 1 1 d . . . . .
H4' H 1.419951 0.777848 0.388243 0.019 Uiso 1 1 calc R U . . .
C5 C 0.5283(4) 0.4052(3) 0.8758(2) 0.0157(5) Uani 1 1 d . . . . .
C5' C 1.2179(3) 0.7528(3) 0.5124(3) 0.0144(5) Uani 1 1 d . . . . .
C6 C 0.6209(4) 0.5033(3) 0.7817(3) 0.0163(5) Uani 1 1 d . . . . .
H6 H 0.563560 0.576850 0.723341 0.020 Uiso 1 1 calc R U . . .
C6' C 1.0562(4) 0.8080(3) 0.5393(2) 0.0146(5) Uani 1 1 d . . . . .
C7 C 0.9038(4) 0.5833(3) 0.6644(3) 0.0163(5) Uani 1 1 d . . . . .
H7A H 0.837550 0.593934 0.595414 0.020 Uiso 1 1 calc R U . . .
H7B H 1.009353 0.527339 0.654823 0.020 Uiso 1 1 calc R U . . .
C7' C 0.8095(4) 0.9829(3) 0.4701(3) 0.0188(6) Uani 1 1 d . . . . .
H7'A H 0.750590 1.007142 0.396267 0.023 Uiso 1 1 calc R U . . .
H7'B H 0.818422 1.073774 0.489766 0.023 Uiso 1 1 calc R U . . .
C8 C 0.9565(3) 0.7376(3) 0.6588(2) 0.0140(5) Uani 1 1 d . . . . .
C8' C 0.7052(4) 0.8734(3) 0.5691(3) 0.0172(5) Uani 1 1 d . . . . .
H8' H 0.680348 0.788235 0.543775 0.021 Uiso 1 1 calc R U . . .
C9 C 1.0554(4) 0.7342(3) 0.7635(3) 0.0176(5) Uani 1 1 d . . . . .
H9A H 1.090642 0.833158 0.754638 0.026 Uiso 1 1 calc R U . . .
H9B H 1.156874 0.670986 0.766351 0.026 Uiso 1 1 calc R U . . .
H9C H 0.982369 0.696197 0.836910 0.026 Uiso 1 1 calc R U . . .
C9' C 0.5382(4) 0.9360(4) 0.6079(3) 0.0208(6) Uani 1 1 d . . . . .
H9'A H 0.484657 0.863797 0.678338 0.031 Uiso 1 1 calc R U . . .
H9'B H 0.461096 0.960129 0.544029 0.031 Uiso 1 1 calc R U . . .
H9'C H 0.561296 1.024410 0.626306 0.031 Uiso 1 1 calc R U . . .
O1A O -0.5247(3) 0.4382(2) 0.51706(19) 0.0181(4) Uani 1 1 d . . . . .
H1A H -0.567118 0.363669 0.568036 0.027 Uiso 1 1 d R U . . .
O1B O 0.4663(3) 1.0377(2) -0.1350(2) 0.0200(5) Uani 1 1 d . . . . .
H1B H 0.404364 1.099935 -0.180655 0.030 Uiso 1 1 d R U . . .
O2A O 0.0039(3) 0.1964(2) 0.6523(2) 0.0185(4) Uani 1 1 d . . . . .
H2AA H -0.062235 0.131801 0.696289 0.028 Uiso 1 1 d R U . . .
O2B O -0.0793(3) 0.8338(2) 0.03475(19) 0.0172(4) Uani 1 1 d . . . . .
H2B H -0.114205 0.873707 -0.032675 0.026 Uiso 1 1 d R U . . .
O3B O 0.1802(3) 0.4326(2) 0.21640(19) 0.0146(4) Uani 1 1 d . . . . .
C1A C -0.0846(4) 0.5016(3) 0.3886(2) 0.0152(5) Uani 1 1 d . . . . .
C1B C 0.3562(3) 0.6810(3) 0.0761(2) 0.0148(5) Uani 1 1 d . . . . .
C2A C -0.2630(4) 0.5143(3) 0.4048(2) 0.0153(5) Uani 1 1 d . . . . .
H2AB H -0.323951 0.587396 0.348517 0.018 Uiso 1 1 calc R U . . .
C2B C 0.4505(4) 0.7961(3) -0.0004(3) 0.0166(5) Uani 1 1 d . . . . .
H2BA H 0.571408 0.787490 -0.009746 0.020 Uiso 1 1 calc R U . . .
C3A C -0.3500(3) 0.4187(3) 0.5040(2) 0.0144(5) Uani 1 1 d . . . . .
C3B C 0.3679(4) 0.9247(3) -0.0635(3) 0.0158(5) Uani 1 1 d . . . . .
C4A C -0.2656(4) 0.3095(3) 0.5875(2) 0.0148(5) Uani 1 1 d . . . . .
H4A H -0.326772 0.244378 0.654248 0.018 Uiso 1 1 calc R U . . .
C4B C 0.1910(4) 0.9370(3) -0.0500(3) 0.0164(5) Uani 1 1 d . . . . .
H4B H 0.134410 1.024875 -0.091931 0.020 Uiso 1 1 calc R U . . .
C5A C -0.0865(4) 0.2982(3) 0.5703(2) 0.0142(5) Uani 1 1 d . . . . .
C5B C 0.0975(3) 0.8203(3) 0.0250(2) 0.0146(5) Uani 1 1 d . . . . .
C6A C 0.0017(3) 0.3912(3) 0.4709(3) 0.0149(5) Uani 1 1 d . . . . .
H6A H 0.121826 0.379458 0.458836 0.018 Uiso 1 1 calc R U . . .
C6B C 0.1764(3) 0.6894(3) 0.0909(2) 0.0131(5) Uani 1 1 d . . . . .
C7A C 0.0121(3) 0.6124(3) 0.2871(2) 0.0144(5) Uani 1 1 d . . . . .
H7AA H 0.113093 0.641753 0.317507 0.017 Uiso 1 1 calc R U . . .
H7AB H -0.062024 0.700141 0.259157 0.017 Uiso 1 1 calc R U . . .
C7B C 0.4511(4) 0.5442(3) 0.1419(3) 0.0171(5) Uani 1 1 d . . . . .
H7BA H 0.558604 0.571318 0.166250 0.021 Uiso 1 1 calc R U . . .
H7BB H 0.481479 0.486559 0.088252 0.021 Uiso 1 1 calc R U . . .
C8A C 0.0743(3) 0.5634(3) 0.1793(2) 0.0131(5) Uani 1 1 d . . . . .
C8B C 0.3469(3) 0.4507(3) 0.2504(2) 0.0152(5) Uani 1 1 d . . . . .
H8B H 0.335147 0.500949 0.311539 0.018 Uiso 1 1 calc R U . . .
C9A C -0.0726(4) 0.5149(3) 0.1263(3) 0.0171(5) Uani 1 1 d . . . . .
H9AA H -0.028983 0.492471 0.055008 0.026 Uiso 1 1 calc R U . . .
H9AB H -0.158823 0.593302 0.105758 0.026 Uiso 1 1 calc R U . . .
H9AC H -0.124246 0.427633 0.184086 0.026 Uiso 1 1 calc R U . . .
C9B C 0.4230(4) 0.2990(3) 0.3034(3) 0.0193(6) Uani 1 1 d . . . . .
H9BA H 0.344053 0.240609 0.367450 0.029 Uiso 1 1 calc R U . . .
H9BB H 0.532128 0.306274 0.334817 0.029 Uiso 1 1 calc R U . . .
H9BC H 0.441910 0.252218 0.242183 0.029 Uiso 1 1 calc R U . . .
O1W O 0.1933(3) 0.2484(2) 0.08292(19) 0.0171(4) Uani 1 1 d . . . . .
H1WA H 0.179363 0.316958 0.115181 0.026 Uiso 1 1 d R U . . .
H1WB H 0.090473 0.230278 0.070441 0.026 Uiso 1 1 d R U . . .
O2W O 0.6926(3) 0.9625(3) 0.1814(2) 0.0255(5) Uani 1 1 d . . . . .
H2WA H 0.585120 0.965437 0.168249 0.038 Uiso 1 1 d R U . . .
H2WB H 0.731721 0.873087 0.182239 0.038 Uiso 1 1 d R U . . .
O3W O 0.3045(3) 0.2684(3) 0.7167(2) 0.0194(5) Uani 1 1 d . . . . .
H3WA H 0.205145 0.235190 0.711931 0.029 Uiso 1 1 d R U . . .
H3WB H 0.282145 0.330120 0.755061 0.029 Uiso 1 1 d R U . . .
O4W O 0.8076(3) 0.9926(2) 0.81757(19) 0.0162(4) Uani 1 1 d . . . . .
H4WA H 0.805098 0.930000 0.779725 0.024 Uiso 1 1 d R U . . .
H4WB H 0.700568 1.012320 0.832396 0.024 Uiso 1 1 d R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8393 . ?
O1 C3 1.366(3) . ?
O1' H1' 0.8401 . ?
O1' C3' 1.375(3) . ?
O2 H2 0.8400 . ?
O2 C5 1.386(3) . ?
O2' H2' 0.8398 . ?
O2' C5' 1.369(3) . ?
O3' C8 1.455(3) . ?
O3' C8' 1.444(4) . ?
C1 C2 1.398(4) . ?
C1 C6 1.407(4) . ?
C1 C7 1.508(4) . ?
C1' C2' 1.406(4) . ?
C1' C6' 1.398(4) . ?
C1' C7' 1.511(4) . ?
C2 H2A 0.9500 . ?
C2 C3 1.391(4) . ?
C2' H2'A 0.9500 . ?
C2' C3' 1.387(4) . ?
C3 C4 1.402(4) . ?
C3' C4' 1.393(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(4) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.396(4) . ?
C5 C6 1.389(4) . ?
C5' C6' 1.410(4) . ?
C6 H6 0.9500 . ?
C6' C8 1.533(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.549(4) . ?
C7' H7'A 0.9900 . ?
C7' H7'B 0.9900 . ?
C7' C8' 1.515(4) . ?
C8 C9 1.525(4) . ?
C8' H8' 1.0000 . ?
C8' C9' 1.522(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9' H9'A 0.9800 . ?
C9' H9'B 0.9800 . ?
C9' H9'C 0.9800 . ?
O1A H1A 0.8400 . ?
O1A C3A 1.379(3) . ?
O1B H1B 0.8405 . ?
O1B C3B 1.372(3) . ?
O2A H2AA 0.8402 . ?
O2A C5A 1.369(3) . ?
O2B H2B 0.8397 . ?
O2B C5B 1.388(3) . ?
O3B C8A 1.451(3) . ?
O3B C8B 1.439(3) . ?
C1A C2A 1.404(4) . ?
C1A C6A 1.395(4) . ?
C1A C7A 1.508(4) . ?
C1B C2B 1.387(4) . ?
C1B C6B 1.410(4) . ?
C1B C7B 1.508(4) . ?
C2A H2AB 0.9500 . ?
C2A C3A 1.392(4) . ?
C2B H2BA 0.9500 . ?
C2B C3B 1.396(4) . ?
C3A C4A 1.388(4) . ?
C3B C4B 1.390(4) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.408(4) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.388(4) . ?
C5A C6A 1.388(4) . ?
C5B C6B 1.409(3) . ?
C6A H6A 0.9500 . ?
C6B C8A 1.535(4) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A C8A 1.552(4) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C7B C8B 1.516(4) . ?
C8A C9A 1.525(4) . ?
C8B H8B 1.0000 . ?
C8B C9B 1.519(4) . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
O1W H1WA 0.8703 . ?
O1W H1WB 0.8696 . ?
O2W H2WA 0.8697 . ?
O2W H2WB 0.9043 . ?
O3W H3WA 0.8702 . ?
O3W H3WB 0.8704 . ?
O4W H4WA 0.8701 . ?
O4W H4WB 0.8702 . ?

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
C3 O1 H1 109.5 . . ?
C3' O1' H1' 109.4 . . ?
C5 O2 H2 109.4 . . ?
C5' O2' H2' 109.5 . . ?
C8' O3' C8 115.5(2) . . ?
C2 C1 C6 119.0(3) . . ?
C2 C1 C7 120.0(3) . . ?
C6 C1 C7 120.7(2) . . ?
C2' C1' C7' 118.1(3) . . ?
C6' C1' C2' 121.1(3) . . ?
C6' C1' C7' 120.8(2) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2A 119.6 . . ?
C1' C2' H2'A 120.0 . . ?
C3' C2' C1' 120.1(3) . . ?
C3' C2' H2'A 120.0 . . ?
O1 C3 C2 118.1(3) . . ?
O1 C3 C4 121.1(3) . . ?
C2 C3 C4 120.7(3) . . ?
O1' C3' C2' 122.6(3) . . ?
O1' C3' C4' 117.4(3) . . ?
C2' C3' C4' 120.1(3) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 H4 121.0 . . ?
C3' C4' H4' 120.2 . . ?
C3' C4' C5' 119.6(3) . . ?
C5' C4' H4' 120.2 . . ?
O2 C5 C4 120.6(2) . . ?
O2 C5 C6 117.2(3) . . ?
C6 C5 C4 122.2(3) . . ?
O2' C5' C4' 119.3(2) . . ?
O2' C5' C6' 119.1(2) . . ?
C4' C5' C6' 121.6(2) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 H6 120.3 . . ?
C1' C6' C5' 117.5(3) . . ?
C1' C6' C8 121.4(2) . . ?
C5' C6' C8 120.9(2) . . ?
C1 C7 H7A 107.8 . . ?
C1 C7 H7B 107.8 . . ?
C1 C7 C8 118.0(2) . . ?
H7A C7 H7B 107.1 . . ?
C8 C7 H7A 107.8 . . ?
C8 C7 H7B 107.8 . . ?
C1' C7' H7'A 109.4 . . ?
C1' C7' H7'B 109.4 . . ?
C1' C7' C8' 111.3(2) . . ?
H7'A C7' H7'B 108.0 . . ?
C8' C7' H7'A 109.4 . . ?
C8' C7' H7'B 109.4 . . ?
O3' C8 C6' 110.5(2) . . ?
O3' C8 C7 109.6(2) . . ?
O3' C8 C9 103.5(2) . . ?
C6' C8 C7 108.1(2) . . ?
C9 C8 C6' 112.9(2) . . ?
C9 C8 C7 112.2(2) . . ?
O3' C8' C7' 108.3(2) . . ?
O3' C8' H8' 109.3 . . ?
O3' C8' C9' 106.7(2) . . ?
C7' C8' H8' 109.3 . . ?
C7' C8' C9' 113.7(2) . . ?
C9' C8' H8' 109.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8' C9' H9'A 109.5 . . ?
C8' C9' H9'B 109.5 . . ?
C8' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C3A O1A H1A 109.2 . . ?
C3B O1B H1B 109.7 . . ?
C5A O2A H2AA 109.8 . . ?
C5B O2B H2B 109.4 . . ?
C8B O3B C8A 116.1(2) . . ?
C2A C1A C7A 119.8(2) . . ?
C6A C1A C2A 119.3(3) . . ?
C6A C1A C7A 120.9(2) . . ?
C2B C1B C6B 121.4(3) . . ?
C2B C1B C7B 118.1(2) . . ?
C6B C1B C7B 120.4(2) . . ?
C1A C2A H2AB 120.3 . . ?
C3A C2A C1A 119.4(3) . . ?
C3A C2A H2AB 120.3 . . ?
C1B C2B H2BA 120.0 . . ?
C1B C2B C3B 120.1(3) . . ?
C3B C2B H2BA 120.0 . . ?
O1A C3A C2A 117.1(2) . . ?
O1A C3A C4A 121.0(2) . . ?
C4A C3A C2A 121.9(3) . . ?
O1B C3B C2B 118.2(2) . . ?
O1B C3B C4B 121.8(3) . . ?
C4B C3B C2B 119.9(3) . . ?
C3A C4A H4A 121.0 . . ?
C3A C4A C5A 118.1(3) . . ?
C5A C4A H4A 121.0 . . ?
C3B C4B H4B 120.2 . . ?
C5B C4B C3B 119.6(2) . . ?
C5B C4B H4B 120.2 . . ?
O2A C5A C4A 120.5(2) . . ?
O2A C5A C6A 118.8(2) . . ?
C6A C5A C4A 120.7(2) . . ?
O2B C5B C6B 119.3(2) . . ?
C4B C5B O2B 118.6(2) . . ?
C4B C5B C6B 122.1(2) . . ?
C1A C6A H6A 119.7 . . ?
C5A C6A C1A 120.6(2) . . ?
C5A C6A H6A 119.7 . . ?
C1B C6B C8A 120.9(2) . . ?
C5B C6B C1B 116.9(2) . . ?
C5B C6B C8A 122.2(2) . . ?
C1A C7A H7AA 108.2 . . ?
C1A C7A H7AB 108.2 . . ?
C1A C7A C8A 116.4(2) . . ?
H7AA C7A H7AB 107.3 . . ?
C8A C7A H7AA 108.2 . . ?
C8A C7A H7AB 108.2 . . ?
C1B C7B H7BA 109.1 . . ?
C1B C7B H7BB 109.1 . . ?
C1B C7B C8B 112.4(2) . . ?
H7BA C7B H7BB 107.9 . . ?
C8B C7B H7BA 109.1 . . ?
C8B C7B H7BB 109.1 . . ?
O3B C8A C6B 110.6(2) . . ?
O3B C8A C7A 110.3(2) . . ?
O3B C8A C9A 102.9(2) . . ?
C6B C8A C7A 107.3(2) . . ?
C9A C8A C6B 113.5(2) . . ?
C9A C8A C7A 112.3(2) . . ?
O3B C8B C7B 108.3(2) . . ?
O3B C8B H8B 109.4 . . ?
O3B C8B C9B 107.0(2) . . ?
C7B C8B H8B 109.4 . . ?
C7B C8B C9B 113.3(2) . . ?
C9B C8B H8B 109.4 . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
C8A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C8B C9B H9BA 109.5 . . ?
C8B C9B H9BB 109.5 . . ?
C8B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
H1WA O1W H1WB 104.5 . . ?
H2WA O2W H2WB 105.8 . . ?
H3WA O3W H3WB 104.5 . . ?
H4WA O4W H4WB 104.5 . . ?

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
O1 H1 O2W 0.84 1.85 2.663(3) 164.2 1_546 yes
O1' H1' O1W 0.84 1.90 2.735(3) 174.8 1_665 yes
O2' H2' O1A 0.84 2.12 2.735(3) 129.4 1_755 yes
O1B H1B O3W 0.84 1.88 2.709(3) 167.1 1_564 yes
O2A H2AA O4W 0.84 1.89 2.720(3) 169.7 1_445 yes
O2B H2B O4W 0.84 1.93 2.761(3) 171.3 1_454 yes
O1W H1WA O3B 0.87 1.90 2.754(3) 165.4 . yes
O1W H1WB O1 0.87 1.86 2.732(3) 178.7 1_454 yes
O2W H2WA O1' 0.87 2.02 2.826(3) 152.9 1_455 yes
O3W H3WA O2A 0.87 1.89 2.733(3) 162.4 . yes
O3W H3WB O2 0.87 2.01 2.785(4) 147.7 . yes
O4W H4WA O3' 0.87 1.90 2.764(3) 169.2 . yes
O4W H4WB O1B 0.87 1.87 2.738(3) 174.9 1_556 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 C5 -179.9(3) . . . . ?
O1' C3' C4' C5' -179.3(3) . . . . ?
O2 C5 C6 C1 -176.3(3) . . . . ?
O2' C5' C6' C1' -178.2(3) . . . . ?
O2' C5' C6' C8 -1.7(4) . . . . ?
C1 C2 C3 O1 179.6(3) . . . . ?
C1 C2 C3 C4 1.6(5) . . . . ?
C1 C7 C8 O3' -58.4(3) . . . . ?
C1 C7 C8 C6' -178.8(2) . . . . ?
C1 C7 C8 C9 56.0(3) . . . . ?
C1' C2' C3' O1' -179.8(3) . . . . ?
C1' C2' C3' C4' 1.1(5) . . . . ?
C1' C6' C8 O3' -10.7(4) . . . . ?
C1' C6' C8 C7 109.2(3) . . . . ?
C1' C6' C8 C9 -126.1(3) . . . . ?
C1' C7' C8' O3' 51.0(3) . . . . ?
C1' C7' C8' C9' 169.5(3) . . . . ?
C2 C1 C6 C5 -1.9(4) . . . . ?
C2 C1 C7 C8 -98.5(3) . . . . ?
C2 C3 C4 C5 -2.0(4) . . . . ?
C2' C1' C6' C5' -2.0(4) . . . . ?
C2' C1' C6' C8 -178.5(3) . . . . ?
C2' C1' C7' C8' 158.2(3) . . . . ?
C2' C3' C4' C5' -0.2(5) . . . . ?
C3 C4 C5 O2 178.2(3) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C3' C4' C5' O2' 179.2(3) . . . . ?
C3' C4' C5' C6' -1.9(4) . . . . ?
C4 C5 C6 C1 1.5(5) . . . . ?
C4' C5' C6' C1' 3.0(4) . . . . ?
C4' C5' C6' C8 179.5(3) . . . . ?
C5' C6' C8 O3' 173.0(2) . . . . ?
C5' C6' C8 C7 -67.1(3) . . . . ?
C5' C6' C8 C9 57.6(3) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
C6 C1 C7 C8 88.2(3) . . . . ?
C6' C1' C2' C3' 0.0(5) . . . . ?
C6' C1' C7' C8' -20.2(4) . . . . ?
C7 C1 C2 C3 -173.0(3) . . . . ?
C7 C1 C6 C5 171.5(3) . . . . ?
C7' C1' C2' C3' -178.4(3) . . . . ?
C7' C1' C6' C5' 176.4(3) . . . . ?
C7' C1' C6' C8 -0.1(4) . . . . ?
C8 O3' C8' C7' -67.5(3) . . . . ?
C8 O3' C8' C9' 169.7(2) . . . . ?
C8' O3' C8 C6' 45.4(3) . . . . ?
C8' O3' C8 C7 -73.6(3) . . . . ?
C8' O3' C8 C9 166.6(2) . . . . ?
O1A C3A C4A C5A -178.4(3) . . . . ?
O1B C3B C4B C5B -178.8(3) . . . . ?
O2A C5A C6A C1A -176.4(3) . . . . ?
O2B C5B C6B C1B 179.1(2) . . . . ?
O2B C5B C6B C8A -3.6(4) . . . . ?
C1A C2A C3A O1A 178.5(3) . . . . ?
C1A C2A C3A C4A -0.7(4) . . . . ?
C1A C7A C8A O3B -56.5(3) . . . . ?
C1A C7A C8A C6B -177.1(2) . . . . ?
C1A C7A C8A C9A 57.6(3) . . . . ?
C1B C2B C3B O1B 177.7(3) . . . . ?
C1B C2B C3B C4B -0.2(4) . . . . ?
C1B C6B C8A O3B -14.5(4) . . . . ?
C1B C6B C8A C7A 105.8(3) . . . . ?
C1B C6B C8A C9A -129.6(3) . . . . ?
C1B C7B C8B O3B 49.5(3) . . . . ?
C1B C7B C8B C9B 168.0(3) . . . . ?
C2A C1A C6A C5A -2.5(4) . . . . ?
C2A C1A C7A C8A -103.6(3) . . . . ?
C2A C3A C4A C5A 0.8(4) . . . . ?
C2B C1B C6B C5B -0.4(4) . . . . ?
C2B C1B C6B C8A -177.7(3) . . . . ?
C2B C1B C7B C8B 160.0(3) . . . . ?
C2B C3B C4B C5B -1.0(4) . . . . ?
C3A C4A C5A O2A 177.3(2) . . . . ?
C3A C4A C5A C6A -1.8(4) . . . . ?
C3B C4B C5B O2B -178.4(3) . . . . ?
C3B C4B C5B C6B 1.6(4) . . . . ?
C4A C5A C6A C1A 2.7(4) . . . . ?
C4B C5B C6B C1B -0.9(4) . . . . ?
C4B C5B C6B C8A 176.4(3) . . . . ?
C5B C6B C8A O3B 168.3(2) . . . . ?
C5B C6B C8A C7A -71.4(3) . . . . ?
C5B C6B C8A C9A 53.2(3) . . . . ?
C6A C1A C2A C3A 1.5(4) . . . . ?
C6A C1A C7A C8A 80.2(3) . . . . ?
C6B C1B C2B C3B 0.9(4) . . . . ?
C6B C1B C7B C8B -21.2(4) . . . . ?
C7A C1A C2A C3A -174.8(3) . . . . ?
C7A C1A C6A C5A 173.7(3) . . . . ?
C7B C1B C2B C3B 179.7(3) . . . . ?
C7B C1B C6B C5B -179.1(3) . . . . ?
C7B C1B C6B C8A 3.6(4) . . . . ?
C8A O3B C8B C7B -66.2(3) . . . . ?
C8A O3B C8B C9B 171.3(2) . . . . ?
C8B O3B C8A C6B 47.2(3) . . . . ?
C8B O3B C8A C7A -71.3(3) . . . . ?
C8B O3B C8A C9A 168.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
