# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

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

data_ge-1
_database_code_depnum_ccdc_archive 'CCDC 1529242'
loop_
_audit_author_name
_audit_author_address
id
;Jinan University
China
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2021-01-28 downloaded from the CCDC.
;
_audit_creation_date             2020-12-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H28 N2 O6, C H4 O'
_chemical_formula_sum            'C25 H32 N2 O7'
_chemical_formula_weight         472.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 O6 N2'
_chemical_oxdiff_usercomment     GW-1
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      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                   10.79250(10)
_cell_length_b                   13.04060(10)
_cell_length_c                   16.29590(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2293.50(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17010
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.7290
_cell_measurement_theta_min      3.4110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.33
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20835
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.869
_diffrn_reflns_theta_min         4.342
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_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    -66.00  32.00   1.00    1.00    --  -41.89  38.00-150.00   98
  2  ω    -96.00  -2.00   1.00    1.00    --  -41.89 125.00  30.00   94
  3  ω     94.00 175.00   1.00    1.00    --  101.33 125.00   0.00   81
  4  ω     75.00 174.00   1.00    1.00    --  101.33  45.00-120.00   99
  5  ω     72.00 174.00   1.00    1.00    --  101.33  61.00 150.00  102
  6  ω     72.00 174.00   1.00    1.00    --  101.33  61.00 -90.00  102
  7  ω     25.00 134.00   1.00    1.00    --  101.33 -77.00   0.00  109
  8  ω   -115.00 -14.00   1.00    1.00    --  -41.89 -57.00  60.00  101
  9  ω   -118.00  -9.00   1.00    1.00    --  -41.89 -77.00-150.00  109
 10  ω     72.00 174.00   1.00    1.00    --  101.33  61.00  90.00  102
 11  ω     72.00 174.00   1.00    1.00    --  101.33  61.00  30.00  102
 12  ω     28.00 121.00   1.00    1.00    --  101.33-125.00 -30.00   93
 13  ω     72.00 174.00   1.00    1.00    --  101.33  61.00 -30.00  102
 14  ω    -70.00 -16.00   1.00    1.00    --  -41.89  57.00 -30.00   54
 15  ω   -118.00  -9.00   1.00    1.00    --  -41.89 -77.00 -30.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1138132000
_diffrn_orient_matrix_UB_12      -0.0514334000
_diffrn_orient_matrix_UB_13      0.0394782000
_diffrn_orient_matrix_UB_21      -0.0481920000
_diffrn_orient_matrix_UB_22      0.1058478000
_diffrn_orient_matrix_UB_23      0.0273041000
_diffrn_orient_matrix_UB_31      -0.0713759000
_diffrn_orient_matrix_UB_32      0.0105445000
_diffrn_orient_matrix_UB_33      -0.0814417000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                4300
_reflns_number_total             4357
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_coef       0.0015(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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.054
_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)+(0.0474P)²+0.4245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0784
_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 Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C14(H14), C15(H15), C16(H16), C1'(H1'), C2'(H2')
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C4'(H4'A,H4'B,H4'C), C5'(H5'A,H5'B,
 H5'C), C1M(H1MA,H1MB,H1MC)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O1M(H1M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N1 N 0.32549(15) 0.52078(14) 0.96906(11) 0.0309(4) Uani 1 1 d . . . . .
N4 N 0.55893(14) 0.70905(12) 0.78310(9) 0.0237(3) Uani 1 1 d . . . . .
O1 O 0.22343(12) 0.45962(11) 0.95254(10) 0.0361(3) Uani 1 1 d . . . . .
O2 O 0.40538(12) 0.51538(11) 0.83877(9) 0.0312(3) Uani 1 1 d . . . . .
O3 O 0.74395(12) 0.58013(11) 0.98623(9) 0.0301(3) Uani 1 1 d . . . . .
O4 O 0.79188(13) 0.43295(10) 0.86307(9) 0.0306(3) Uani 1 1 d . . . . .
H4 H 0.770259 0.374121 0.873577 0.046 Uiso 1 1 calc R U . . .
O5 O 0.36127(13) 0.75871(12) 0.59485(9) 0.0362(3) Uani 1 1 d . . . . .
O6 O 0.45521(12) 0.62391(10) 0.65083(8) 0.0275(3) Uani 1 1 d . . . . .
C2 C 0.41501(17) 0.53835(13) 0.91043(12) 0.0252(4) Uani 1 1 d . . . . .
C3 C 0.64668(16) 0.52808(14) 0.94450(12) 0.0248(4) Uani 1 1 d . . . . .
H3 H 0.634426 0.463626 0.974347 0.030 Uiso 1 1 calc R U . . .
C5 C 0.61866(17) 0.73619(13) 0.86156(12) 0.0250(4) Uani 1 1 d . . . . .
H5 H 0.630731 0.810653 0.862853 0.030 Uiso 1 1 calc R U . . .
C6 C 0.53831(17) 0.70590(14) 0.93498(11) 0.0260(4) Uani 1 1 d . . . . .
H6A H 0.455920 0.733295 0.925764 0.031 Uiso 1 1 calc R U . . .
H6B H 0.571466 0.740150 0.983041 0.031 Uiso 1 1 calc R U . . .
C7 C 0.52444(17) 0.59027(14) 0.95612(11) 0.0245(4) Uani 1 1 d . . . . .
C8 C 0.48306(18) 0.58271(15) 1.04538(12) 0.0273(4) Uani 1 1 d . . . . .
C9 C 0.5423(2) 0.61081(16) 1.11744(12) 0.0336(4) Uani 1 1 d . . . . .
H9 H 0.620901 0.639942 1.116169 0.040 Uiso 1 1 calc R U . . .
C10 C 0.4816(2) 0.59452(18) 1.19196(13) 0.0402(5) Uani 1 1 d . . . . .
H10 H 0.520803 0.612234 1.240750 0.048 Uiso 1 1 calc R U . . .
C11 C 0.3643(2) 0.55257(17) 1.19436(14) 0.0411(5) Uani 1 1 d . . . . .
H11 H 0.325399 0.543413 1.244755 0.049 Uiso 1 1 calc R U . . .
C12 C 0.3029(2) 0.52361(16) 1.12265(14) 0.0368(5) Uani 1 1 d . . . . .
H12 H 0.224299 0.494394 1.123976 0.044 Uiso 1 1 calc R U . . .
C13 C 0.36451(19) 0.54046(14) 1.04964(13) 0.0292(4) Uani 1 1 d . . . . .
C14 C 0.68507(16) 0.49721(13) 0.85716(12) 0.0231(4) Uani 1 1 d . . . . .
H14 H 0.617362 0.459794 0.830540 0.028 Uiso 1 1 calc R U . . .
C15 C 0.72188(16) 0.59063(14) 0.80458(12) 0.0243(4) Uani 1 1 d . . . . .
H15 H 0.793928 0.574779 0.770246 0.029 Uiso 1 1 calc R U . . .
C16 C 0.74693(17) 0.68456(14) 0.85826(12) 0.0265(4) Uani 1 1 d . . . . .
H16 H 0.803401 0.730087 0.828427 0.032 Uiso 1 1 calc R U . . .
C17 C 0.80559(19) 0.65914(16) 0.94082(13) 0.0321(4) Uani 1 1 d . . . . .
H17A H 0.890744 0.638304 0.931627 0.039 Uiso 1 1 calc R U . . .
H17B H 0.807217 0.720924 0.973947 0.039 Uiso 1 1 calc R U . . .
C18 C 0.5843(2) 0.47429(14) 0.66442(13) 0.0312(4) Uani 1 1 d . . . . .
H18A H 0.522495 0.446671 0.700525 0.047 Uiso 1 1 calc R U . . .
H18B H 0.664568 0.449794 0.680651 0.047 Uiso 1 1 calc R U . . .
H18C H 0.567418 0.452890 0.609176 0.047 Uiso 1 1 calc R U . . .
C19 C 0.58208(17) 0.59058(14) 0.66900(11) 0.0243(4) Uani 1 1 d . . . . .
C20 C 0.61546(16) 0.63180(13) 0.75265(12) 0.0232(4) Uani 1 1 d . . . . .
C21 C 0.1164(2) 0.5223(2) 0.93886(17) 0.0445(6) Uani 1 1 d . . . . .
H21A H 0.096706 0.559094 0.988192 0.067 Uiso 1 1 calc R U . . .
H21B H 0.047581 0.479664 0.923726 0.067 Uiso 1 1 calc R U . . .
H21C H 0.133179 0.570155 0.895495 0.067 Uiso 1 1 calc R U . . .
C1' C 0.65928(18) 0.64346(14) 0.60063(12) 0.0259(4) Uani 1 1 d . . . . .
H1' H 0.655622 0.599913 0.551684 0.031 Uiso 1 1 calc R U . . .
C4' C 0.79510(18) 0.66475(17) 0.61904(13) 0.0330(4) Uani 1 1 d . . . . .
H4'A H 0.833034 0.696641 0.572265 0.049 Uiso 1 1 calc R U . . .
H4'B H 0.836706 0.601405 0.630920 0.049 Uiso 1 1 calc R U . . .
H4'C H 0.801231 0.709648 0.665553 0.049 Uiso 1 1 calc R U . . .
C3' C 0.45582(18) 0.71304(14) 0.60888(12) 0.0264(4) Uani 1 1 d . . . . .
C2' C 0.58528(17) 0.74087(14) 0.58271(12) 0.0258(4) Uani 1 1 d . . . . .
H2' H 0.615880 0.796281 0.617918 0.031 Uiso 1 1 calc R U . . .
C5' C 0.58867(19) 0.77653(15) 0.49356(13) 0.0318(4) Uani 1 1 d . . . . .
H5'A H 0.560299 0.722189 0.458546 0.048 Uiso 1 1 calc R U . . .
H5'B H 0.672017 0.794656 0.478972 0.048 Uiso 1 1 calc R U . . .
H5'C H 0.535817 0.835190 0.487085 0.048 Uiso 1 1 calc R U . . .
O1M O 0.28662(18) 0.75240(18) 0.80351(17) 0.0731(7) Uani 1 1 d . . . . .
H1M H 0.356412 0.737020 0.787884 0.110 Uiso 1 1 calc R U . . .
C1M C 0.2026(3) 0.6963(2) 0.7627(2) 0.0604(7) Uani 1 1 d . . . . .
H1MA H 0.123344 0.702871 0.788847 0.091 Uiso 1 1 calc R U . . .
H1MB H 0.227488 0.625632 0.762831 0.091 Uiso 1 1 calc R U . . .
H1MC H 0.196969 0.720310 0.707103 0.091 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O1 1.386(2) . ?
N1 C2 1.378(3) . ?
N1 C13 1.403(3) . ?
N4 C5 1.475(2) . ?
N4 C20 1.278(2) . ?
O1 C21 1.433(3) . ?
O2 C2 1.210(2) . ?
O3 C3 1.423(2) . ?
O3 C17 1.432(3) . ?
O4 H4 0.8200 . ?
O4 C14 1.428(2) . ?
O5 C3' 1.203(2) . ?
O6 C19 1.467(2) . ?
O6 C3' 1.348(2) . ?
C2 C7 1.552(3) . ?
C3 H3 0.9800 . ?
C3 C7 1.560(2) . ?
C3 C14 1.536(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.530(3) . ?
C5 C16 1.540(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.554(3) . ?
C7 C8 1.525(3) . ?
C8 C9 1.386(3) . ?
C8 C13 1.395(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.396(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.396(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.541(3) . ?
C15 H15 0.9800 . ?
C15 C16 1.529(3) . ?
C15 C20 1.524(2) . ?
C16 H16 0.9800 . ?
C16 C17 1.523(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 C19 1.518(3) . ?
C19 C20 1.509(3) . ?
C19 C1' 1.553(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C1' H1' 0.9800 . ?
C1' C4' 1.522(3) . ?
C1' C2' 1.529(2) . ?
C4' H4'A 0.9600 . ?
C4' H4'B 0.9600 . ?
C4' H4'C 0.9600 . ?
C3' C2' 1.505(3) . ?
C2' H2' 0.9800 . ?
C2' C5' 1.526(3) . ?
C5' H5'A 0.9600 . ?
C5' H5'B 0.9600 . ?
C5' H5'C 0.9600 . ?
O1M H1M 0.8200 . ?
O1M C1M 1.341(4) . ?
C1M H1MA 0.9600 . ?
C1M H1MB 0.9600 . ?
C1M H1MC 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
O1 N1 C13 121.70(16) . . ?
C2 N1 O1 121.20(17) . . ?
C2 N1 C13 114.09(16) . . ?
C20 N4 C5 108.49(15) . . ?
N1 O1 C21 110.04(15) . . ?
C3 O3 C17 116.03(15) . . ?
C14 O4 H4 109.5 . . ?
C3' O6 C19 110.69(14) . . ?
N1 C2 C7 105.87(15) . . ?
O2 C2 N1 124.59(18) . . ?
O2 C2 C7 129.53(17) . . ?
O3 C3 H3 105.8 . . ?
O3 C3 C7 108.53(14) . . ?
O3 C3 C14 111.64(15) . . ?
C7 C3 H3 105.8 . . ?
C14 C3 H3 105.8 . . ?
C14 C3 C7 118.48(15) . . ?
N4 C5 H5 108.3 . . ?
N4 C5 C6 111.61(15) . . ?
N4 C5 C16 104.93(14) . . ?
C6 C5 H5 108.3 . . ?
C6 C5 C16 115.09(16) . . ?
C16 C5 H5 108.3 . . ?
C5 C6 H6A 107.7 . . ?
C5 C6 H6B 107.7 . . ?
C5 C6 C7 118.60(15) . . ?
H6A C6 H6B 107.1 . . ?
C7 C6 H6A 107.7 . . ?
C7 C6 H6B 107.7 . . ?
C2 C7 C3 111.01(14) . . ?
C2 C7 C6 112.98(15) . . ?
C6 C7 C3 113.33(15) . . ?
C8 C7 C2 101.93(15) . . ?
C8 C7 C3 109.26(15) . . ?
C8 C7 C6 107.60(15) . . ?
C9 C8 C7 130.99(18) . . ?
C9 C8 C13 119.02(19) . . ?
C13 C8 C7 109.98(17) . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.7(2) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.3(2) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 121.6 . . ?
C13 C12 C11 116.7(2) . . ?
C13 C12 H12 121.6 . . ?
C8 C13 N1 107.52(17) . . ?
C12 C13 N1 129.27(19) . . ?
C12 C13 C8 123.2(2) . . ?
O4 C14 C3 108.00(14) . . ?
O4 C14 H14 109.8 . . ?
O4 C14 C15 107.05(14) . . ?
C3 C14 H14 109.8 . . ?
C3 C14 C15 112.18(15) . . ?
C15 C14 H14 109.8 . . ?
C14 C15 H15 110.8 . . ?
C16 C15 C14 111.13(15) . . ?
C16 C15 H15 110.8 . . ?
C20 C15 C14 113.14(14) . . ?
C20 C15 H15 110.8 . . ?
C20 C15 C16 99.71(14) . . ?
C5 C16 H16 108.1 . . ?
C15 C16 C5 102.19(14) . . ?
C15 C16 H16 108.1 . . ?
C17 C16 C5 115.96(17) . . ?
C17 C16 C15 113.85(16) . . ?
C17 C16 H16 108.1 . . ?
O3 C17 C16 114.82(15) . . ?
O3 C17 H17A 108.6 . . ?
O3 C17 H17B 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
O6 C19 C18 107.52(16) . . ?
O6 C19 C20 107.44(14) . . ?
O6 C19 C1' 102.97(14) . . ?
C18 C19 C1' 113.56(16) . . ?
C20 C19 C18 113.35(16) . . ?
C20 C19 C1' 111.21(15) . . ?
N4 C20 C15 114.95(16) . . ?
N4 C20 C19 121.17(16) . . ?
C19 C20 C15 123.78(15) . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C1' H1' 107.8 . . ?
C4' C1' C19 117.16(16) . . ?
C4' C1' H1' 107.8 . . ?
C4' C1' C2' 112.91(16) . . ?
C2' C1' C19 103.05(14) . . ?
C2' C1' H1' 107.8 . . ?
C1' C4' H4'A 109.5 . . ?
C1' C4' H4'B 109.5 . . ?
C1' C4' H4'C 109.5 . . ?
H4'A C4' H4'B 109.5 . . ?
H4'A C4' H4'C 109.5 . . ?
H4'B C4' H4'C 109.5 . . ?
O5 C3' O6 121.25(18) . . ?
O5 C3' C2' 127.87(17) . . ?
O6 C3' C2' 110.85(15) . . ?
C1' C2' H2' 108.9 . . ?
C3' C2' C1' 103.32(15) . . ?
C3' C2' H2' 108.9 . . ?
C3' C2' C5' 111.44(16) . . ?
C5' C2' C1' 115.01(16) . . ?
C5' C2' H2' 108.9 . . ?
C2' C5' H5'A 109.5 . . ?
C2' C5' H5'B 109.5 . . ?
C2' C5' H5'C 109.5 . . ?
H5'A C5' H5'B 109.5 . . ?
H5'A C5' H5'C 109.5 . . ?
H5'B C5' H5'C 109.5 . . ?
C1M O1M H1M 109.5 . . ?
O1M C1M H1MA 109.5 . . ?
O1M C1M H1MB 109.5 . . ?
O1M C1M H1MC 109.5 . . ?
H1MA C1M H1MB 109.5 . . ?
H1MA C1M H1MC 109.5 . . ?
H1MB C1M H1MC 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
N1 C2 C7 C3 123.27(16) . . . . ?
N1 C2 C7 C6 -108.15(17) . . . . ?
N1 C2 C7 C8 7.02(18) . . . . ?
N4 C5 C6 C7 71.5(2) . . . . ?
N4 C5 C16 C15 -29.78(18) . . . . ?
N4 C5 C16 C17 -154.21(16) . . . . ?
O1 N1 C2 O2 10.5(3) . . . . ?
O1 N1 C2 C7 -168.89(15) . . . . ?
O1 N1 C13 C8 166.31(16) . . . . ?
O1 N1 C13 C12 -13.8(3) . . . . ?
O2 C2 C7 C3 -56.1(3) . . . . ?
O2 C2 C7 C6 72.5(2) . . . . ?
O2 C2 C7 C8 -172.36(19) . . . . ?
O3 C3 C7 C2 178.89(14) . . . . ?
O3 C3 C7 C6 50.5(2) . . . . ?
O3 C3 C7 C8 -69.48(19) . . . . ?
O3 C3 C14 O4 58.52(18) . . . . ?
O3 C3 C14 C15 -59.21(18) . . . . ?
O4 C14 C15 C16 -101.84(17) . . . . ?
O4 C14 C15 C20 146.95(15) . . . . ?
O5 C3' C2' C1' -167.2(2) . . . . ?
O5 C3' C2' C5' -43.2(3) . . . . ?
O6 C19 C20 N4 -22.2(2) . . . . ?
O6 C19 C20 C15 161.77(15) . . . . ?
O6 C19 C1' C4' 154.48(16) . . . . ?
O6 C19 C1' C2' 29.86(17) . . . . ?
O6 C3' C2' C1' 11.0(2) . . . . ?
O6 C3' C2' C5' 135.03(16) . . . . ?
C2 N1 O1 C21 -103.3(2) . . . . ?
C2 N1 C13 C8 5.7(2) . . . . ?
C2 N1 C13 C12 -174.40(19) . . . . ?
C2 C7 C8 C9 176.6(2) . . . . ?
C2 C7 C8 C13 -3.99(19) . . . . ?
C3 O3 C17 C16 7.3(2) . . . . ?
C3 C7 C8 C9 59.1(3) . . . . ?
C3 C7 C8 C13 -121.50(16) . . . . ?
C3 C14 C15 C16 16.5(2) . . . . ?
C3 C14 C15 C20 -94.75(18) . . . . ?
C5 N4 C20 C15 1.1(2) . . . . ?
C5 N4 C20 C19 -175.34(15) . . . . ?
C5 C6 C7 C2 -88.7(2) . . . . ?
C5 C6 C7 C3 38.6(2) . . . . ?
C5 C6 C7 C8 159.56(16) . . . . ?
C5 C16 C17 O3 68.1(2) . . . . ?
C6 C5 C16 C15 93.29(18) . . . . ?
C6 C5 C16 C17 -31.1(2) . . . . ?
C6 C7 C8 C9 -64.3(3) . . . . ?
C6 C7 C8 C13 115.06(17) . . . . ?
C7 C3 C14 O4 -174.31(15) . . . . ?
C7 C3 C14 C15 68.0(2) . . . . ?
C7 C8 C9 C10 -179.8(2) . . . . ?
C7 C8 C13 N1 -0.5(2) . . . . ?
C7 C8 C13 C12 179.60(18) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C9 C8 C13 N1 179.00(18) . . . . ?
C9 C8 C13 C12 -0.9(3) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
C11 C12 C13 N1 -178.9(2) . . . . ?
C11 C12 C13 C8 0.9(3) . . . . ?
C13 N1 O1 C21 97.4(2) . . . . ?
C13 N1 C2 O2 171.26(18) . . . . ?
C13 N1 C2 C7 -8.2(2) . . . . ?
C13 C8 C9 C10 0.8(3) . . . . ?
C14 C3 C7 C2 50.3(2) . . . . ?
C14 C3 C7 C6 -78.1(2) . . . . ?
C14 C3 C7 C8 161.90(16) . . . . ?
C14 C15 C16 C5 -91.15(16) . . . . ?
C14 C15 C16 C17 34.7(2) . . . . ?
C14 C15 C20 N4 98.15(19) . . . . ?
C14 C15 C20 C19 -85.6(2) . . . . ?
C15 C16 C17 O3 -50.1(2) . . . . ?
C16 C5 C6 C7 -47.9(2) . . . . ?
C16 C15 C20 N4 -19.9(2) . . . . ?
C16 C15 C20 C19 156.36(16) . . . . ?
C17 O3 C3 C7 -86.10(19) . . . . ?
C17 O3 C3 C14 46.3(2) . . . . ?
C18 C19 C20 N4 -140.80(18) . . . . ?
C18 C19 C20 C15 43.1(2) . . . . ?
C18 C19 C1' C4' -89.6(2) . . . . ?
C18 C19 C1' C2' 145.81(17) . . . . ?
C19 O6 C3' O5 -172.69(18) . . . . ?
C19 O6 C3' C2' 9.0(2) . . . . ?
C19 C1' C2' C3' -24.80(18) . . . . ?
C19 C1' C2' C5' -146.46(16) . . . . ?
C20 N4 C5 C6 -106.75(17) . . . . ?
C20 N4 C5 C16 18.53(19) . . . . ?
C20 C15 C16 C5 28.42(17) . . . . ?
C20 C15 C16 C17 154.24(16) . . . . ?
C20 C19 C1' C4' 39.7(2) . . . . ?
C20 C19 C1' C2' -84.92(17) . . . . ?
C1' C19 C20 N4 89.8(2) . . . . ?
C1' C19 C20 C15 -86.3(2) . . . . ?
C4' C1' C2' C3' -152.16(16) . . . . ?
C4' C1' C2' C5' 86.2(2) . . . . ?
C3' O6 C19 C18 -144.85(15) . . . . ?
C3' O6 C19 C20 92.82(17) . . . . ?
C3' O6 C19 C1' -24.66(18) . . . . ?

_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 1.872
_oxdiff_exptl_absorpt_empirical_full_min 0.751
####################################################################### 
# 
# 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_ge-8
_database_code_depnum_ccdc_archive 'CCDC 2048837'
loop_
_audit_author_name
_audit_author_address
ZW
;Jinan University
China
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2021-01-28 downloaded from the CCDC.
;
_audit_creation_date             2020-03-08
_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         'C25 H26 N2 O6, H2 O'
_chemical_formula_sum            'C25 H28 N2 O7'
_chemical_formula_weight         468.49
_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'
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      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                   6.78030(10)
_cell_length_b                   16.8379(2)
_cell_length_c                   19.3294(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2206.76(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10114
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2030
_cell_measurement_theta_min      3.4550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (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    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14125
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.679
_diffrn_reflns_theta_min         3.481
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00  -2.00   1.00    1.00    --  -41.11 125.00 -60.00   94
  2  ω   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00   0.00  100
  3  ω   -114.00 -58.00   1.00    1.00    --  -41.11-148.00-171.00   56
  4  ω     24.00 109.00   1.00    1.32    --  106.95 -94.00 -90.00   85
  5  ω     34.00 133.00   1.00    1.32    --  106.95 -45.00  90.00   99
  6  ω     34.00 121.00   1.00    1.32    --  106.95-125.00  90.00   87
  7  ω     94.00 178.00   1.00    1.32    --  106.95 125.00-180.00   84
  8  ω     24.00 109.00   1.00    1.32    --  106.95 -94.00-180.00   85
  9  ω     54.00 178.00   1.00    1.32    --  106.95  15.00   0.00  124
 10  ω   -116.00 -17.00   1.00    1.00    --  -41.11 -37.00-150.00   99
 11  ω   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00 120.00  100
 12  ω     54.00 124.00   1.00    1.32    --  106.95  15.00 120.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0241449000
_diffrn_orient_matrix_UB_12      -0.0764067000
_diffrn_orient_matrix_UB_13      0.0430251000
_diffrn_orient_matrix_UB_21      0.0715712000
_diffrn_orient_matrix_UB_22      -0.0496964000
_diffrn_orient_matrix_UB_23      -0.0620389000
_diffrn_orient_matrix_UB_31      0.2142495000
_diffrn_orient_matrix_UB_32      0.0079921000
_diffrn_orient_matrix_UB_33      0.0255714000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                4231
_reflns_number_total             4358
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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         0.249
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 1708 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.056
_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)+(0.0703P)²+0.3857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1077
_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:
 O009(H00Y,H)
2.b Ternary CH refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00N(H00N), C00O(H00O), C00U(H00U)
2.c Secondary CH2 refined with riding coordinates:
 C00L(H00A,H00B), C00T(H00H,H00I), C00W(H00L,H00R)
2.d Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00K(H00K), C00M(H00M), C00P(H00P), C00Q(H00Q), C00V(H00V),
 C00X(H00X)
2.e Idealised Me refined as rotating group:
 C00S(H00C,H00D,H00F), C00Y(H00S,H00T,H00W)
2.f Idealised tetrahedral OH refined as rotating group:
 O003(H003), O006(H006)
;
_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 0.6793(2) 0.41857(10) 0.45453(9) 0.0169(4) Uani 1 1 d . . . . .
O002 O 0.6398(3) 0.65291(10) 0.65730(8) 0.0173(4) Uani 1 1 d . . . . .
O003 O 0.6868(2) 0.58501(9) 0.41735(9) 0.0158(3) Uani 1 1 d . . . . .
H003 H 0.787607 0.559518 0.424776 0.024 Uiso 1 1 calc GR . . . .
O004 O 0.0768(2) 0.52617(10) 0.43886(9) 0.0177(4) Uani 1 1 d . . . . .
O005 O -0.0813(2) 0.44775(11) 0.32388(9) 0.0200(4) Uani 1 1 d . . . . .
O006 O 0.9348(3) 0.53667(10) 0.68095(10) 0.0211(4) Uani 1 1 d . . . . .
H006 H 1.025965 0.536204 0.653065 0.032 Uiso 1 1 calc GR . . . .
N007 N 0.2538(3) 0.51953(12) 0.59032(10) 0.0160(4) Uani 1 1 d . . . . .
N008 N 0.0689(3) 0.41984(13) 0.36557(11) 0.0181(4) Uani 1 1 d . . . . .
O009 O 1.0126(4) 0.42367(14) 0.78354(13) 0.0432(6) Uani 1 1 d . . . . .
H00Y H 0.968635 0.460662 0.757912 0.065 Uiso 1 1 d G . . . .
H H 0.920982 0.415330 0.812671 0.065 Uiso 1 1 d G . . . .
C00A C 0.3496(3) 0.57903(14) 0.56638(12) 0.0149(4) Uani 1 1 d . . . . .
C00B C 0.3156(4) 0.34078(14) 0.40230(12) 0.0159(5) Uani 1 1 d . . . . .
C00C C 0.1416(3) 0.46186(14) 0.41941(12) 0.0148(5) Uani 1 1 d . . . . .
C00D C 0.5519(4) 0.72276(15) 0.63542(13) 0.0180(5) Uani 1 1 d . . . . .
C00E C 0.3737(3) 0.44683(14) 0.58122(12) 0.0160(5) Uani 1 1 d . . . . .
H00E H 0.374126 0.417933 0.625232 0.019 Uiso 1 1 calc R . . . .
C00F C 0.2680(3) 0.66090(14) 0.56947(12) 0.0163(5) Uani 1 1 d . . . . .
C00G C 0.5854(3) 0.47785(14) 0.56787(13) 0.0171(5) Uani 1 1 d . . . . .
H00G H 0.646938 0.488474 0.612808 0.021 Uiso 1 1 calc R . . . .
C00H C 0.1618(4) 0.34627(14) 0.35467(13) 0.0171(5) Uani 1 1 d . . . . .
C00I C 0.8157(4) 0.67387(15) 0.68749(12) 0.0196(5) Uani 1 1 d . . . . .
C00J C 0.4365(4) 0.27479(14) 0.40025(13) 0.0191(5) Uani 1 1 d . . . . .
H00J H 0.540833 0.269636 0.431175 0.023 Uiso 1 1 calc R . . . .
C00K C 0.3647(4) 0.72156(15) 0.59962(13) 0.0182(5) Uani 1 1 d . . . . .
H00K H 0.301058 0.770386 0.596999 0.022 Uiso 1 1 calc R . . . .
C00L C 0.2973(4) 0.39056(13) 0.52507(12) 0.0160(5) Uani 1 1 d . . . . .
H00A H 0.158203 0.381618 0.533843 0.019 Uiso 1 1 calc R . . . .
H00B H 0.363500 0.339972 0.531144 0.019 Uiso 1 1 calc R . . . .
C00M C 0.1171(4) 0.28852(15) 0.30689(13) 0.0208(5) Uani 1 1 d . . . . .
H00M H 0.010394 0.293272 0.276928 0.025 Uiso 1 1 calc R . . . .
C00N C 0.5252(3) 0.54917(14) 0.45315(12) 0.0140(5) Uani 1 1 d . . . . .
H00N H 0.403613 0.575899 0.438695 0.017 Uiso 1 1 calc R . . . .
C00O C 0.5122(3) 0.46157(13) 0.43095(12) 0.0144(5) Uani 1 1 d . . . . .
H00O H 0.522396 0.461973 0.380372 0.017 Uiso 1 1 calc R . . . .
C00P C 0.6689(4) 0.78515(15) 0.65312(13) 0.0223(5) Uani 1 1 d . . . . .
H00P H 0.642537 0.838589 0.645199 0.027 Uiso 1 1 calc R . . . .
C00Q C 0.3996(4) 0.21592(15) 0.35098(13) 0.0219(5) Uani 1 1 d . . . . .
H00Q H 0.482218 0.171932 0.348296 0.026 Uiso 1 1 calc R . . . .
C00R C 0.3192(3) 0.41469(14) 0.44758(12) 0.0145(5) Uani 1 1 d . . . . .
C00S C 0.0042(4) 0.49233(16) 0.26713(14) 0.0241(5) Uani 1 1 d . . . . .
H00C H -0.099153 0.516721 0.240641 0.036 Uiso 1 1 calc GR . . . .
H00D H 0.078282 0.457106 0.237981 0.036 Uiso 1 1 calc GR . . . .
H00F H 0.089964 0.532671 0.285183 0.036 Uiso 1 1 calc GR . . . .
C00T C 0.7216(3) 0.42436(15) 0.52738(12) 0.0189(5) Uani 1 1 d . . . . .
H00H H 0.855529 0.443535 0.532932 0.023 Uiso 1 1 calc R . . . .
H00I H 0.715601 0.371510 0.547255 0.023 Uiso 1 1 calc R . . . .
C00U C 0.5451(3) 0.55785(14) 0.53273(12) 0.0147(5) Uani 1 1 d . . . . .
H00U H 0.647015 0.596776 0.544658 0.018 Uiso 1 1 calc R . . . .
C00V C 0.8386(4) 0.75338(15) 0.68591(14) 0.0232(5) Uani 1 1 d . . . . .
H00V H 0.945265 0.781964 0.703068 0.028 Uiso 1 1 calc R . . . .
C00W C 0.9380(4) 0.60913(16) 0.71861(14) 0.0223(5) Uani 1 1 d . . . . .
H00L H 1.073386 0.627378 0.721937 0.027 Uiso 1 1 calc R . . . .
H00R H 0.891340 0.599040 0.765219 0.027 Uiso 1 1 calc R . . . .
C00X C 0.2407(4) 0.22249(15) 0.30598(13) 0.0224(5) Uani 1 1 d . . . . .
H00X H 0.216405 0.181863 0.274519 0.027 Uiso 1 1 calc R . . . .
C00Y C 0.0694(4) 0.67349(15) 0.53729(13) 0.0206(5) Uani 1 1 d . . . . .
H00S H 0.077920 0.664687 0.488310 0.031 Uiso 1 1 calc GR . . . .
H00T H 0.026473 0.726921 0.545869 0.031 Uiso 1 1 calc GR . . . .
H00W H -0.023468 0.636930 0.557072 0.031 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00O 1.420(3) . ?
O001 C00T 1.440(3) . ?
O002 C00D 1.385(3) . ?
O002 C00I 1.374(3) . ?
O003 C00N 1.429(3) . ?
O004 C00C 1.228(3) . ?
O005 N008 1.381(3) . ?
O005 C00S 1.450(3) . ?
O006 C00W 1.421(3) . ?
N007 C00A 1.280(3) . ?
N007 C00E 1.480(3) . ?
N008 C00C 1.351(3) . ?
N008 C00H 1.406(3) . ?
C00A C00F 1.486(3) . ?
C00A C00U 1.519(3) . ?
C00B C00H 1.394(4) . ?
C00B C00J 1.382(3) . ?
C00B C00R 1.522(3) . ?
C00C C00R 1.542(3) . ?
C00D C00K 1.446(4) . ?
C00D C00P 1.360(4) . ?
C00E C00G 1.549(3) . ?
C00E C00L 1.531(3) . ?
C00F C00K 1.346(4) . ?
C00F C00Y 1.499(3) . ?
C00G C00T 1.509(3) . ?
C00G C00U 1.533(3) . ?
C00H C00M 1.375(3) . ?
C00I C00V 1.348(4) . ?
C00I C00W 1.496(4) . ?
C00J C00Q 1.397(4) . ?
C00L C00R 1.559(3) . ?
C00M C00X 1.393(4) . ?
C00N C00O 1.539(3) . ?
C00N C00U 1.551(3) . ?
C00O C00R 1.562(3) . ?
C00P C00V 1.418(4) . ?
C00Q C00X 1.389(4) . ?

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
C00O O001 C00T 115.98(18) . . ?
C00I O002 C00D 106.56(19) . . ?
N008 O005 C00S 108.85(19) . . ?
C00A N007 C00E 109.0(2) . . ?
O005 N008 C00H 122.9(2) . . ?
C00C N008 O005 122.7(2) . . ?
C00C N008 C00H 114.4(2) . . ?
N007 C00A C00F 121.5(2) . . ?
N007 C00A C00U 114.4(2) . . ?
C00F C00A C00U 124.0(2) . . ?
C00H C00B C00R 109.7(2) . . ?
C00J C00B C00H 118.6(2) . . ?
C00J C00B C00R 131.7(2) . . ?
O004 C00C N008 124.5(2) . . ?
O004 C00C C00R 128.7(2) . . ?
N008 C00C C00R 106.69(19) . . ?
O002 C00D C00K 120.8(2) . . ?
C00P C00D O002 109.2(2) . . ?
C00P C00D C00K 130.0(2) . . ?
N007 C00E C00G 104.47(18) . . ?
N007 C00E C00L 114.22(19) . . ?
C00L C00E C00G 113.8(2) . . ?
C00A C00F C00Y 116.7(2) . . ?
C00K C00F C00A 122.7(2) . . ?
C00K C00F C00Y 120.7(2) . . ?
C00T C00G C00E 116.9(2) . . ?
C00T C00G C00U 113.8(2) . . ?
C00U C00G C00E 101.82(18) . . ?
C00B C00H N008 107.1(2) . . ?
C00M C00H N008 128.7(2) . . ?
C00M C00H C00B 124.2(2) . . ?
O002 C00I C00W 117.7(2) . . ?
C00V C00I O002 110.2(2) . . ?
C00V C00I C00W 132.0(3) . . ?
C00B C00J C00Q 118.9(2) . . ?
C00F C00K C00D 130.2(2) . . ?
C00E C00L C00R 119.19(19) . . ?
C00H C00M C00X 116.1(2) . . ?
O003 C00N C00O 108.26(18) . . ?
O003 C00N C00U 111.95(18) . . ?
C00O C00N C00U 111.84(19) . . ?
O001 C00O C00N 110.72(19) . . ?
O001 C00O C00R 110.17(17) . . ?
C00N C00O C00R 118.35(19) . . ?
C00D C00P C00V 107.1(2) . . ?
C00X C00Q C00J 120.6(2) . . ?
C00B C00R C00C 101.86(18) . . ?
C00B C00R C00L 109.75(18) . . ?
C00B C00R C00O 107.97(18) . . ?
C00C C00R C00L 113.52(19) . . ?
C00C C00R C00O 108.75(18) . . ?
C00L C00R C00O 114.16(19) . . ?
O001 C00T C00G 115.20(19) . . ?
C00A C00U C00G 99.92(18) . . ?
C00A C00U C00N 111.77(18) . . ?
C00G C00U C00N 111.85(19) . . ?
C00I C00V C00P 106.9(2) . . ?
O006 C00W C00I 114.3(2) . . ?
C00Q C00X C00M 121.5(2) . . ?

_olex2_date_sample_data_collection 2017-11-30
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.413
_oxdiff_exptl_absorpt_empirical_full_min 0.705
####################################################################### 
# 
# 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_i4r1
_database_code_depnum_ccdc_archive 'CCDC 1966232'
loop_
_audit_author_name
_audit_author_address
GF
;jnu
China
;
_audit_update_record             
;
2019-11-18 deposited with the CCDC.	2021-01-28 downloaded from the CCDC.
;
_audit_creation_date             2018-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H36 N2 O7'
_chemical_formula_sum            'C29 H36 N2 O7'
_chemical_formula_weight         524.60
_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'
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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   25.5600(12)
_cell_length_b                   7.9389(3)
_cell_length_c                   13.7603(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.827(4)
_cell_angle_gamma                90
_cell_volume                     2782.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9358
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.8320
_cell_measurement_theta_min      3.4450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (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    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14756
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.981
_diffrn_reflns_theta_min         3.223
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  39.00   1.00    1.00    --  -40.98  19.00 -90.00   98
  2  ω     50.00  92.00   1.00    1.00    --   40.98-125.00 -30.00   42
  3  ω     35.00 129.00   1.00    6.00    --  107.58 -45.00 -90.00   94
  4  ω     84.00 120.00   1.00    6.00    --  107.58 -77.00-150.00   36
  5  ω     53.00 171.00   1.00    6.00    --  107.58   0.00-180.00  118
  6  ω    140.00 178.00   1.00    6.00    --  107.58  77.00 -90.00   38
  7  ω    144.00 178.00   1.00    6.00    --  107.58  45.00  30.00   34
  8  ω    102.00 137.00   1.00    6.00    --  107.58 -61.00  60.00   35
  9  ω     67.00 122.00   1.00    6.00    --  107.58-125.00  30.00   55
 10  ω     54.00 110.00   1.00    6.00    --  107.58 -95.00 150.00   56
 11  ω     35.00  79.00   1.00    6.00    --  107.58 -61.00  60.00   44
 12  ω     27.00 110.00   1.00    6.00    --  107.58 -95.00  60.00   83
 13  ω     23.00  96.00   1.00    1.00    --   40.98-125.00  90.00   73
 14  ω     92.00 178.00   1.00    6.00    --  107.58  45.00-150.00   86
 15  ω     79.00 110.00   1.00    6.00    --  107.58  77.00 -90.00   31
 16  ω     41.00  98.00   1.00    6.00    --  107.58 -61.00-180.00   57
 17  ω    -71.00  -2.00   1.00    1.00    --  -40.98 125.00 -90.00   69
 18  ω   -111.00 -17.00   1.00    1.00    --  -40.98 -38.00  90.00   94
 19  ω    -60.00 -25.00   1.00    1.00    --  -41.23 -38.00 -90.00   35
 20  ω    -74.00  -9.00   1.00    1.00    --  -41.23 -77.00  30.00   65
 21  ω     18.00  44.00   1.00    1.00    --   41.23  57.00 -30.00   26
 22  ω     75.00 101.00   1.00    6.00    --  107.58  77.00   0.00   26
 23  ω    131.00 157.00   1.00    6.00    --  107.58  77.00  60.00   26
 24  ω     75.00 101.00   1.00    6.00    --  107.58  77.00 -30.00   26
 25  ω     75.00 100.00   1.00    6.00    --  107.58  77.00  60.00   25
 26  ω     78.00 104.00   1.00    6.00    --  107.58  61.00  60.00   26
 27  ω     79.00 105.00   1.00    6.00    --  107.58  61.00   0.00   26
 28  ω     79.00 105.00   1.00    6.00    --  107.58  61.00  30.00   26
 29  ω     83.00 109.00   1.00    6.00    --  107.58  61.00 -60.00   26
 30  ω     80.00 120.00   1.00    6.00    --  107.58  61.00 -30.00   40
 31  ω     75.00 101.00   1.00    8.00    --  107.58  77.00  30.00   26
 32  ω     82.00 108.00   1.00    8.00    --  107.58  45.00 -30.00   26
 33  ω     83.00 109.00   1.00    8.00    --  107.58  45.00  30.00   26
 34  ω     82.00 133.00   1.00    8.00    --  107.58  45.00   0.00   51
 35  ω     82.00 108.00   1.00    8.00    --  107.58  45.00  90.00   26
 36  ω     81.00 107.00   1.00    8.00    --  107.58  61.00  90.00   26
 37  ω     82.00 108.00   1.00    8.00    --  107.58  30.00 -30.00   26
 38  ω     84.00 110.00   1.00    8.00    --  107.58  30.00  90.00   26
 39  ω     75.00 101.00   1.00    8.00    --  107.58  77.00 -60.00   26
 40  ω     84.00 121.00   1.00    8.00    --  107.58  45.00  60.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0543737000
_diffrn_orient_matrix_UB_12      -0.0455340000
_diffrn_orient_matrix_UB_13      -0.0329038000
_diffrn_orient_matrix_UB_21      0.0219057000
_diffrn_orient_matrix_UB_22      -0.0149601000
_diffrn_orient_matrix_UB_23      0.1074383000
_diffrn_orient_matrix_UB_31      -0.0149194000
_diffrn_orient_matrix_UB_32      -0.1880476000
_diffrn_orient_matrix_UB_33      -0.0007218000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.895
_reflns_Friedel_fraction_max     0.861
_reflns_number_gt                5007
_reflns_number_total             5255
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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         0.920
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 2001 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5255
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0622
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1143P)²+1.2006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1630
_refine_ls_wR_factor_ref         0.1669
_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 Ternary CH refined with riding coordinates:
 C16(H16), C5(H5), C14(H14), C15(H15), C4'(H4'), C5'(H5'), C3(H3), C9'(H9'),
 C6'(H6'), C8'(H8')
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C17(H17A,H17B), C11'(H11A,H11B), C1'(H1'A,H1'B), C7'(H7'A,H7'B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C10(H10), C9(H9)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C21'(H21A,H21B,H21C), C10'(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O7(H7), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_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
O3 O 0.70576(9) 0.7095(3) 0.69618(17) 0.0238(5) Uani 1 1 d . . . . .
O5 O 0.85978(10) 0.1721(3) 0.6882(2) 0.0311(6) Uani 1 1 d . . . . .
O2 O 0.86754(10) 0.5912(4) 0.83286(18) 0.0307(6) Uani 1 1 d . . . . .
N4 N 0.83971(11) 0.4370(3) 0.63764(19) 0.0205(5) Uani 1 1 d . . . . .
N1 N 0.81596(13) 0.6038(4) 0.9614(2) 0.0281(6) Uani 1 1 d . . . . .
C16 C 0.76188(12) 0.5733(4) 0.5802(2) 0.0222(6) Uani 1 1 d . . . . .
H16 H 0.760445 0.542619 0.511003 0.027 Uiso 1 1 calc R . . . .
O1 O 0.85572(12) 0.6236(4) 1.03432(19) 0.0358(7) Uani 1 1 d . . . . .
O4 O 0.77489(10) 0.9742(3) 0.66271(19) 0.0270(5) Uani 1 1 d . . . . .
H4 H 0.798982 1.042169 0.661582 0.040 Uiso 1 1 calc GR . . . .
C2 C 0.82471(14) 0.5886(4) 0.8653(2) 0.0244(6) Uani 1 1 d . . . . .
O7 O 1.04189(11) 0.3886(5) 0.7396(2) 0.0426(7) Uani 1 1 d . . . . .
H7 H 1.071361 0.420949 0.729072 0.064 Uiso 1 1 calc GR . . . .
C5 C 0.78252(12) 0.4193(4) 0.6403(2) 0.0207(6) Uani 1 1 d . . . . .
H5 H 0.771137 0.316442 0.605280 0.025 Uiso 1 1 calc R . . . .
C7 C 0.76979(13) 0.5677(4) 0.8089(2) 0.0224(6) Uani 1 1 d . . . . .
C6 C 0.76554(12) 0.4096(4) 0.7442(2) 0.0214(6) Uani 1 1 d . . . . .
H6A H 0.786079 0.321523 0.778152 0.026 Uiso 1 1 calc R . . . .
H6B H 0.729191 0.373142 0.739762 0.026 Uiso 1 1 calc R . . . .
C17 C 0.70794(14) 0.6345(5) 0.6014(2) 0.0262(7) Uani 1 1 d . . . . .
H17A H 0.695979 0.716583 0.552260 0.031 Uiso 1 1 calc R . . . .
H17B H 0.683800 0.540033 0.595737 0.031 Uiso 1 1 calc R . . . .
C14 C 0.79570(13) 0.8123(4) 0.6907(2) 0.0229(6) Uani 1 1 d . . . . .
H14 H 0.828933 0.826319 0.730834 0.027 Uiso 1 1 calc R . . . .
C15 C 0.80501(13) 0.7069(4) 0.5995(2) 0.0222(6) Uani 1 1 d . . . . .
H15 H 0.805493 0.781265 0.542743 0.027 Uiso 1 1 calc R . . . .
C3' C 0.87431(13) 0.3154(5) 0.6674(2) 0.0240(7) Uani 1 1 d . . . . .
C20 C 0.85403(13) 0.6019(4) 0.6086(2) 0.0218(6) Uani 1 1 d . . . . .
C12 C 0.74216(18) 0.5823(5) 1.0692(2) 0.0343(8) Uani 1 1 d . . . . .
H12 H 0.762483 0.603277 1.127175 0.041 Uiso 1 1 calc R . . . .
C11 C 0.68845(18) 0.5510(5) 1.0676(3) 0.0334(8) Uani 1 1 d . . . . .
H11 H 0.672455 0.550963 1.125838 0.040 Uiso 1 1 calc R . . . .
C13 C 0.76369(15) 0.5806(5) 0.9808(2) 0.0275(7) Uani 1 1 d . . . . .
C8 C 0.73441(15) 0.5528(4) 0.8919(2) 0.0262(7) Uani 1 1 d . . . . .
C10 C 0.65846(17) 0.5201(5) 0.9809(3) 0.0333(8) Uani 1 1 d . . . . .
H10 H 0.622754 0.498303 0.981855 0.040 Uiso 1 1 calc R . . . .
C4' C 0.93134(14) 0.3695(4) 0.6775(3) 0.0262(7) Uani 1 1 d . . . . .
H4' H 0.937410 0.428831 0.739874 0.031 Uiso 1 1 calc R . . . .
C11' C 0.94245(14) 0.4941(5) 0.5972(3) 0.0288(7) Uani 1 1 d . . . . .
H11A H 0.977293 0.541072 0.611280 0.035 Uiso 1 1 calc R . . . .
H11B H 0.941906 0.434664 0.535528 0.035 Uiso 1 1 calc R . . . .
C5' C 0.96823(14) 0.2157(5) 0.6817(3) 0.0297(7) Uani 1 1 d . . . . .
H5' H 0.956660 0.143658 0.626162 0.036 Uiso 1 1 calc R . . . .
C19 C 0.90285(14) 0.6354(5) 0.5881(3) 0.0253(7) Uani 1 1 d . . . . .
O6 O 0.98789(15) 0.3203(6) 0.9005(3) 0.0580(10) Uani 1 1 d . . . . .
H6 H 0.996814 0.372671 0.853264 0.087 Uiso 1 1 calc GR . . . .
C3 C 0.75479(12) 0.7333(4) 0.7521(2) 0.0220(6) Uani 1 1 d . . . . .
H3 H 0.748202 0.817259 0.801902 0.026 Uiso 1 1 calc R . . . .
C18 C 0.92006(16) 0.8022(5) 0.5517(3) 0.0344(8) Uani 1 1 d . . . . .
H18A H 0.891722 0.881397 0.552461 0.052 Uiso 1 1 calc GR . . . .
H18B H 0.929912 0.790070 0.486274 0.052 Uiso 1 1 calc GR . . . .
H18C H 0.949588 0.842126 0.593037 0.052 Uiso 1 1 calc GR . . . .
C9' C 0.96989(17) 0.1015(6) 0.7757(3) 0.0407(9) Uani 1 1 d . . . . .
H9' H 0.945577 0.007347 0.762186 0.049 Uiso 1 1 calc R . . . .
C6' C 1.02572(16) 0.2572(6) 0.6722(3) 0.0369(9) Uani 1 1 d . . . . .
H6' H 1.031193 0.290641 0.605282 0.044 Uiso 1 1 calc R . . . .
C9 C 0.68128(15) 0.5211(5) 0.8917(3) 0.0279(7) Uani 1 1 d . . . . .
H9 H 0.661012 0.500909 0.833528 0.033 Uiso 1 1 calc R . . . .
C8' C 1.0268(2) 0.0292(7) 0.7881(4) 0.0498(12) Uani 1 1 d . . . . .
H8' H 1.044748 0.084779 0.845091 0.060 Uiso 1 1 calc R . . . .
C1' C 0.9554(2) 0.1890(8) 0.8689(3) 0.0509(12) Uani 1 1 d . . . . .
H1'A H 0.919794 0.231610 0.857873 0.061 Uiso 1 1 calc R . . . .
H1'B H 0.955617 0.105687 0.920518 0.061 Uiso 1 1 calc R . . . .
C7' C 1.05314(19) 0.0916(7) 0.6980(4) 0.0470(11) Uani 1 1 d . . . . .
H7'A H 1.090499 0.108459 0.713362 0.056 Uiso 1 1 calc R . . . .
H7'B H 1.047940 0.011803 0.644628 0.056 Uiso 1 1 calc R . . . .
C21' C 0.8792(3) 0.4614(7) 1.0579(4) 0.0599(16) Uani 1 1 d . . . . .
H21A H 0.892994 0.414811 1.000942 0.090 Uiso 1 1 calc GR . . . .
H21B H 0.853138 0.386818 1.080013 0.090 Uiso 1 1 calc GR . . . .
H21C H 0.907166 0.474825 1.108478 0.090 Uiso 1 1 calc GR . . . .
C10' C 1.0298(3) -0.1561(9) 0.8067(6) 0.0748(19) Uani 1 1 d . . . . .
H10A H 1.065878 -0.189014 0.819193 0.112 Uiso 1 1 calc GR . . . .
H10B H 1.014373 -0.215482 0.750660 0.112 Uiso 1 1 calc GR . . . .
H10C H 1.011068 -0.182975 0.862349 0.112 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
O3 C17 1.439(4) . ?
O3 C3 1.427(4) . ?
O5 C3' 1.238(5) . ?
O2 C2 1.217(5) . ?
N4 C5 1.472(4) . ?
N4 C3' 1.349(4) . ?
N4 C20 1.425(4) . ?
N1 O1 1.376(4) . ?
N1 C2 1.364(4) . ?
N1 C13 1.397(5) . ?
C16 C5 1.544(5) . ?
C16 C17 1.513(5) . ?
C16 C15 1.537(4) . ?
O1 C21' 1.446(5) . ?
O4 C14 1.431(4) . ?
C2 C7 1.555(5) . ?
O7 C6' 1.433(5) . ?
C5 C6 1.531(4) . ?
C7 C6 1.537(4) . ?
C7 C8 1.520(5) . ?
C7 C3 1.561(5) . ?
C14 C15 1.543(4) . ?
C14 C3 1.533(5) . ?
C15 C20 1.501(5) . ?
C3' C4' 1.515(5) . ?
C20 C19 1.329(5) . ?
C12 C11 1.393(7) . ?
C12 C13 1.376(5) . ?
C11 C10 1.384(6) . ?
C13 C8 1.397(5) . ?
C8 C9 1.381(6) . ?
C10 C9 1.403(5) . ?
C4' C11' 1.527(5) . ?
C4' C5' 1.541(5) . ?
C11' C19 1.510(5) . ?
C5' C9' 1.577(6) . ?
C5' C6' 1.522(5) . ?
C19 C18 1.494(5) . ?
O6 C1' 1.381(8) . ?
C9' C8' 1.559(6) . ?
C9' C1' 1.531(7) . ?
C6' C7' 1.518(6) . ?
C8' C7' 1.542(8) . ?
C8' C10' 1.494(8) . ?

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 O3 C17 116.4(2) . . ?
C3' N4 C5 123.4(3) . . ?
C3' N4 C20 124.4(3) . . ?
C20 N4 C5 112.0(3) . . ?
O1 N1 C13 122.3(3) . . ?
C2 N1 O1 123.1(3) . . ?
C2 N1 C13 114.3(3) . . ?
C17 C16 C5 115.2(3) . . ?
C17 C16 C15 113.4(3) . . ?
C15 C16 C5 104.2(2) . . ?
N1 O1 C21' 109.3(3) . . ?
O2 C2 N1 125.5(3) . . ?
O2 C2 C7 128.4(3) . . ?
N1 C2 C7 106.2(3) . . ?
N4 C5 C16 101.9(2) . . ?
N4 C5 C6 112.9(2) . . ?
C6 C5 C16 115.4(3) . . ?
C2 C7 C3 109.5(3) . . ?
C6 C7 C2 113.1(3) . . ?
C6 C7 C3 113.3(2) . . ?
C8 C7 C2 101.7(3) . . ?
C8 C7 C6 110.7(3) . . ?
C8 C7 C3 107.8(3) . . ?
C5 C6 C7 119.2(3) . . ?
O3 C17 C16 114.4(3) . . ?
O4 C14 C15 110.3(3) . . ?
O4 C14 C3 105.1(3) . . ?
C3 C14 C15 112.7(3) . . ?
C16 C15 C14 111.0(3) . . ?
C20 C15 C16 102.3(3) . . ?
C20 C15 C14 114.7(3) . . ?
O5 C3' N4 121.7(3) . . ?
O5 C3' C4' 123.0(3) . . ?
N4 C3' C4' 115.2(3) . . ?
N4 C20 C15 107.5(3) . . ?
C19 C20 N4 120.8(3) . . ?
C19 C20 C15 131.5(3) . . ?
C13 C12 C11 116.8(3) . . ?
C10 C11 C12 121.2(3) . . ?
N1 C13 C8 107.6(3) . . ?
C12 C13 N1 128.9(3) . . ?
C12 C13 C8 123.4(4) . . ?
C13 C8 C7 109.7(3) . . ?
C9 C8 C7 131.3(3) . . ?
C9 C8 C13 119.0(3) . . ?
C11 C10 C9 120.8(4) . . ?
C3' C4' C11' 110.7(3) . . ?
C3' C4' C5' 111.1(3) . . ?
C11' C4' C5' 112.9(3) . . ?
C19 C11' C4' 112.2(3) . . ?
C4' C5' C9' 117.4(3) . . ?
C6' C5' C4' 114.7(3) . . ?
C6' C5' C9' 103.6(3) . . ?
C20 C19 C11' 117.9(3) . . ?
C20 C19 C18 123.8(3) . . ?
C18 C19 C11' 118.2(3) . . ?
O3 C3 C7 109.0(3) . . ?
O3 C3 C14 111.4(3) . . ?
C14 C3 C7 118.1(3) . . ?
C8' C9' C5' 105.2(4) . . ?
C1' C9' C5' 115.8(4) . . ?
C1' C9' C8' 111.4(4) . . ?
O7 C6' C5' 109.3(3) . . ?
O7 C6' C7' 112.2(4) . . ?
C7' C6' C5' 102.9(4) . . ?
C8 C9 C10 118.7(4) . . ?
C7' C8' C9' 105.1(4) . . ?
C10' C8' C9' 114.6(5) . . ?
C10' C8' C7' 115.7(5) . . ?
O6 C1' C9' 115.1(4) . . ?
C6' C7' C8' 104.0(4) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.734 0.000 38.5 2.3 ?
2 0.147 0.626 0.668 58.4 17.0 ?
3 0.353 0.126 0.332 58.4 17.0 ?
4 0.500 0.234 1.000 38.5 2.3 ?
5 0.647 0.126 0.668 58.4 17.0 ?
6 0.853 0.626 0.332 58.4 17.0 ?


_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.859
_oxdiff_exptl_absorpt_empirical_full_min 0.539
