# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_rev2
_database_code_depnum_ccdc_archive 'CCDC 2427253'
loop_
_audit_author_name
_audit_author_address
'Laszlo Fabian'
;University of East Anglia
United Kingdom
;
_audit_update_record             
;
2025-10-07 deposited with the CCDC.	2025-10-15 downloaded from the CCDC.
;
_audit_creation_date             2025-09-11
_audit_creation_method           
; 
Olex2 1.5 
(compiled 2025.07.13 svn.rb7424ae for OlexSys, GUI svn.r7314) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'artesunate 4-aminobenzoic acid'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H28 O8, C7 H7 N O2'
_chemical_formula_sum            'C26 H35 N O10'
_chemical_formula_weight         521.55
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           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                   5.69290(10)
_cell_length_b                   17.0162(2)
_cell_length_c                   13.4451(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.1350(10)
_cell_angle_gamma                90
_cell_volume                     1294.99(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10715
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      76.4160
_cell_measurement_theta_min      3.2700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14940
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.419
_diffrn_reflns_theta_min         3.306
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -20.00   0.50    0.66    --  -91.75  45.00  30.00   62
  2  ω    -51.00 -22.00   0.50    0.66    --  -91.75  61.00 -30.00   58
  3  ω    -50.00 -21.00   0.50    0.66    --  -91.75  45.00 -90.00   58
  4  ω    -62.00  23.00   0.50    0.16    --  -47.29  57.00-180.00  170
  5  ω    -50.00 -21.00   0.50    0.66    --  -91.75  45.00-180.00   58
  6  ω    -49.00 -20.00   0.50    0.66    --  -91.75  45.00 -60.00   58
  7  ω    -51.00 -22.00   0.50    0.66    --  -91.75  45.00  90.00   58
  8  ω    -48.00 -21.00   0.50    0.66    --  -91.75  45.00 150.00   54
  9  ω     -6.00  26.00   0.50    0.16    --  -47.29  37.00  60.00   64
 10  ω    121.00 177.00   0.50    0.66    --  106.64  61.00 -90.00  112
 11  ω    130.00 167.00   0.50    0.66    --  106.64  61.00-120.00   74
 12  ω     96.00 176.00   0.50    0.66    --  106.64 125.00 -60.00  160
 13  ω    146.00 172.00   0.50    0.66    --  106.64  83.00 -31.00   52
 14  ω    101.00 133.00   0.50    0.66    --  106.64  83.00 -31.00   64
 15  ω    101.00 131.00   0.50    0.66    --  106.64  15.00 -90.00   60
 16  ω     41.00  66.00   0.50    0.66    --  106.64 -61.00  60.00   50
 17  ω     44.00  71.00   0.50    0.66    --  106.64 -61.00 120.00   54
 18  ω     35.00  71.00   0.50    0.66    --  106.64 -61.00 -30.00   72
 19  ω    -27.00  19.00   0.50    0.16    --   47.29 -19.00 -90.00   92
 20  ω    -15.00  18.00   0.50    0.16    --   47.29 -19.00 -60.00   66
 21  ω     50.00 101.00   0.50    0.66    --  106.64 -83.00-151.00  102
 22  ω     44.00 105.00   0.50    0.66    --  106.64 -94.00-150.00  122
 23  ω     66.00 107.00   0.50    0.66    --  106.64-125.00  30.00   82
 24  ω     39.00  73.00   0.50    0.66    --  106.64-125.00 -30.00   68
 25  ω      2.00  32.00   0.50    0.16    --   47.29 -83.00-151.00   60
 26  ω    -72.00   7.00   0.50    0.16    --  -47.29  83.00 -31.00  158
 27  ω    -68.00 -21.00   0.50    0.66    --  -91.75  83.00 -31.00   94
 28  ω   -113.00 -37.00   0.50    0.16    --  -47.29 -37.00 120.00  152
 29  ω   -161.00-115.00   0.50    0.66    --  -91.75 -61.00 150.00   92
 30  ω   -161.00-103.00   0.50    0.66    --  -91.75 -61.00 120.00  116
 31  ω   -163.00-111.00   0.50    0.66    --  -91.75 -77.00  90.00  104
 32  ω   -162.00-126.00   0.50    0.66    --  -91.75 -45.00  60.00   72
 33  ω   -124.00 -78.00   0.50    0.66    --  -91.75 -15.00  90.00   92
 34  ω   -106.00 -79.00   0.50    0.66    --  -91.75 -45.00  60.00   54
 35  ω   -111.00 -84.00   0.50    0.66    --  -91.75 -15.00  30.00   54
 36  ω   -164.00-138.00   0.50    0.66    --  -91.75 -15.00  30.00   52
 37  ω   -123.00 -82.00   0.50    0.66    --  -91.75 -45.00 -90.00   82
 38  ω   -132.00 -80.00   0.50    0.66    --  -91.75 -45.00-120.00  104
 39  ω   -145.00-120.00   0.50    0.66    --  -91.75 -83.00-151.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0432758000
_diffrn_orient_matrix_UB_12      0.0020506000
_diffrn_orient_matrix_UB_13      0.1111480000
_diffrn_orient_matrix_UB_21      0.1299539000
_diffrn_orient_matrix_UB_22      0.0793893000
_diffrn_orient_matrix_UB_23      0.0124077000
_diffrn_orient_matrix_UB_31      -0.2351915000
_diffrn_orient_matrix_UB_32      0.0434452000
_diffrn_orient_matrix_UB_33      -0.0278804000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                4810
_reflns_number_total             5007
_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 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2118 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.09(8)
_refine_ls_extinction_coef       0.0027(4)
_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   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5007
_refine_ls_number_restraints     243
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.040
_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)+(0.0345P)²+0.3023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0847
_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,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2. Restrained distances 
 O9B-H9B = O9C-H9B = O21-H21 
 0.84 with sigma of 0.02 
 C1B-C2B \\sim C1C-C2C 
 with sigma of 0.02 
 C1B-C6B \\sim C1C-C6C 
 with sigma of 0.02 
 C1B-C7B \\sim C1C-C7C 
 with sigma of 0.02 
 C2B-C3B \\sim C2C-C3C 
 with sigma of 0.02 
 C3B-C4B \\sim C3C-C4C 
 with sigma of 0.02 
 C4B-N4B \\sim C4C-N4C 
 with sigma of 0.02 
 C4B-C5B \\sim C4C-C5C 
 with sigma of 0.02 
 C5B-C6B \\sim C5C-C6C 
 with sigma of 0.02 
 C7B-O8B \\sim C7C-O8C 
 with sigma of 0.02 
 C7B-O9B \\sim C7C-O9C 
 with sigma of 0.02 
 C1B-C3B \\sim C1C-C3C 
 with sigma of 0.04 
 C1B-C5B \\sim C1C-C5C 
 with sigma of 0.04 
 C1B-O8B \\sim C1C-O8C 
 with sigma of 0.04 
 C1B-O9B \\sim C1C-O9C 
 with sigma of 0.04 
 C2B-C4B \\sim C2C-C4C 
 with sigma of 0.04 
 C2B-C6B \\sim C2C-C6C 
 with sigma of 0.04 
 C2B-C7B \\sim C2C-C7C 
 with sigma of 0.04 
 C3B-N4B \\sim C3C-N4C 
 with sigma of 0.04 
 C3B-C5B \\sim C3C-C5C 
 with sigma of 0.04 
 C4B-C6B \\sim C4C-C6C 
 with sigma of 0.04 
 N4B-C5B \\sim N4C-C5C 
 with sigma of 0.04 
 C6B-C7B \\sim C6C-C7C 
 with sigma of 0.04 
 O8B-O9B \\sim O8C-O9C 
 with sigma of 0.04 
 C6-C7 \\sim C6-C7D 
 with sigma of 0.02 
 C7-C8 \\sim C7D-C8D 
 with sigma of 0.02 
 C8-C8A \\sim C8D-C8E 
 with sigma of 0.02 
 C8A-C9 \\sim C8E-C9D 
 with sigma of 0.02 
 C8A-C12A \\sim C8E-C12A 
 with sigma of 0.02 
 C9-C9M \\sim C9D-C9N 
 with sigma of 0.02 
 C9-C10 \\sim C9D-C10 
 with sigma of 0.02 
 C6-C8 \\sim C6-C8D 
 with sigma of 0.04 
 C7-C8A \\sim C7D-C8E 
 with sigma of 0.04 
 C8-C9 \\sim C8D-C9D 
 with sigma of 0.04 
 C8-C12A \\sim C8D-C12A 
 with sigma of 0.04 
 C8A-C9M \\sim C8E-C9N 
 with sigma of 0.04 
 C8A-C10 \\sim C8E-C10 
 with sigma of 0.04 
 C9-C12A \\sim C9D-C12A 
 with sigma of 0.04 
 C9M-C10 \\sim C9N-C10 
 with sigma of 0.04 
3. Uiso/Uaniso restraints and constraints 
Uanis(C1B) = Uanis(C1C) 
Uanis(C2B) = Uanis(C2C) 
Uanis(C6B) = Uanis(C6C) 
Uanis(C7B) = Uanis(C7C) 
Uanis(C3B) = Uanis(C3C) 
Uanis(N4B) = Uanis(N4C) 
Uanis(C4B) = Uanis(C4C) 
Uanis(C5B) = Uanis(C5C) 
Uanis(O8B) = Uanis(O8C) 
Uanis(O9B) = Uanis(O9C) 
4. Rigid body (RIGU) restrains 
 C7C, C1C, C2C, C6C, C3C, C5C, O8C, O9C, C4C, N4C 
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 
 C6B, C1B, C2B, C7B, C3B, C5B, O8B, O9B, C4B, N4B 
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 
 C9, C9M, C8A, C12A, C8, C7, C6 
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 
 C6, C7D, C8D, C8E, C9D, C10 
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 
5. Others 
 Sof(C1C)=Sof(C2C)=Sof(H2C)=Sof(C3C)=Sof(H3C)=Sof(C4C)=Sof(N4C)=Sof(H4CA)= 
 Sof(H4CB)=Sof(C5C)=Sof(H5C)=Sof(C6C)=Sof(H6C)=Sof(C7C)=Sof(O8C)=Sof(O9C)=1- 
 FVAR(1) 
 Sof(C1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(N4B)=Sof(H4BA)= 
 Sof(H4BB)=Sof(C5B)=Sof(H5BA)=Sof(C6B)=Sof(H6BA)=Sof(C7B)=Sof(O8B)=Sof(O9B)= 
 FVAR(1) 
 Sof(H6B)=Sof(H10A)=Sof(C9D)=Sof(H9D)=Sof(C9N)=Sof(H9NA)=Sof(H9NB)=Sof(H9NC)= 
 Sof(C8E)=Sof(H8E)=Sof(C8D)=Sof(H8DA)=Sof(H8DB)=Sof(C7D)=Sof(H7DA)=Sof(H7DB)=1- 
 FVAR(2) 
 Sof(H6A)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C8A)= 
 Sof(H8AA)=Sof(C9)=Sof(H9)=Sof(C9M)=Sof(H9MA)=Sof(H9MB)=Sof(H9MC)=Sof(H10)= 
 FVAR(2) 
6.a Ternary CH refined with riding coordinates: 
 C5A(H5AA), C6(H6A), C6(H6B), C8A(H8AA), C9(H9), C10(H10), C10(H10A), C12(H12), 
  C9D(H9D), C8E(H8E) 
6.b Secondary CH2 refined with riding coordinates: 
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C17(H17A,H17B), C18(H18A, 
 H18B), C8D(H8DA,H8DB), C7D(H7DA,H7DB) 
6.c Aromatic/amide H refined with riding coordinates: 
 C2B(H2B), C3B(H3B), C5B(H5BA), C6B(H6BA), C2C(H2C), C3C(H3C), C5C(H5C), 
 C6C(H6C) 
6.d X=CH2 refined with riding coordinates: 
 N4B(H4BA,H4BB), N4C(H4CA,H4CB) 
6.e Idealised Me refined as rotating group: 
 C3M(H3MA,H3MB,H3MC), C6M(H6MA,H6MB,H6MC), C9M(H9MA,H9MB,H9MC), C9N(H9NA,H9NB, 
 H9NC) 
;
_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 1.0236(3) 0.62563(14) 0.72107(16) 0.0490(6) Uani 1 1 d . . . . .
O2 O 1.0455(3) 0.69023(15) 0.65026(19) 0.0540(6) Uani 1 1 d . . . . .
C3 C 0.9063(5) 0.75337(19) 0.6772(3) 0.0504(8) Uani 1 1 d . . . . .
C3M C 0.9726(9) 0.8189(2) 0.6098(4) 0.0837(15) Uani 1 1 d . . . . .
H3MA H 0.978959 0.798464 0.542000 0.126 Uiso 1 1 calc R U . . .
H3MB H 1.127706 0.839883 0.635323 0.126 Uiso 1 1 calc R U . . .
H3MC H 0.854205 0.860765 0.608411 0.126 Uiso 1 1 calc R U . . .
C4 C 0.9435(6) 0.7733(2) 0.7887(3) 0.0585(10) Uani 1 1 d . . . . .
H4A H 1.104785 0.757021 0.815591 0.070 Uiso 1 1 calc R U . . .
H4B H 0.933108 0.831045 0.796559 0.070 Uiso 1 1 calc R U . . .
C5 C 0.7670(5) 0.73469(17) 0.8505(2) 0.0418(6) Uani 1 1 d . . . . .
H5A H 0.607748 0.755340 0.827733 0.050 Uiso 1 1 calc R U . . .
H5B H 0.805366 0.750670 0.921146 0.050 Uiso 1 1 calc R U . . .
C5A C 0.7575(5) 0.64487(16) 0.84606(19) 0.0352(6) Uani 1 1 d . . . . .
H5AA H 0.899330 0.625527 0.889431 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5422(5) 0.61392(15) 0.89223(18) 0.0348(6) Uani 1 1 d D . . . .
H6A H 0.393792 0.631057 0.851466 0.042 Uiso 0.49(3) 1 calc R U P A 1
H6B H 0.402418 0.639741 0.854244 0.042 Uiso 0.51(3) 1 calc R U P A 2
C6M C 0.5403(6) 0.64070(17) 1.0011(2) 0.0467(7) Uani 1 1 d . . . . .
H6MA H 0.689126 0.625507 1.039693 0.070 Uiso 1 1 calc R U . . .
H6MB H 0.408012 0.615747 1.029947 0.070 Uiso 1 1 calc R U . . .
H6MC H 0.522488 0.697939 1.003124 0.070 Uiso 1 1 calc R U . . .
C7 C 0.570(2) 0.5242(5) 0.8861(8) 0.0283(19) Uani 0.49(3) 1 d D . P A 1
H7A H 0.718980 0.508855 0.925852 0.034 Uiso 0.49(3) 1 calc R U P A 1
H7B H 0.438409 0.499148 0.917033 0.034 Uiso 0.49(3) 1 calc R U P A 1
C8 C 0.571(2) 0.4921(6) 0.7799(7) 0.0259(18) Uani 0.49(3) 1 d D . P A 1
H8A H 0.582298 0.434069 0.782440 0.031 Uiso 0.49(3) 1 calc R U P A 1
H8B H 0.421409 0.506259 0.739748 0.031 Uiso 0.49(3) 1 calc R U P A 1
C8A C 0.778(3) 0.5248(7) 0.7296(9) 0.0291(19) Uani 0.49(3) 1 d D . P A 1
H8AA H 0.925485 0.505280 0.768958 0.035 Uiso 0.49(3) 1 calc R U P A 1
C9 C 0.790(2) 0.4986(7) 0.6212(8) 0.029(2) Uani 0.49(3) 1 d D . P A 1
H9 H 0.940961 0.517761 0.598203 0.035 Uiso 0.49(3) 1 calc R U P A 1
C9M C 0.780(3) 0.4089(4) 0.6126(6) 0.036(2) Uani 0.49(3) 1 d D . P A 1
H9MA H 0.881948 0.385517 0.668244 0.055 Uiso 0.49(3) 1 calc R U P A 1
H9MB H 0.834967 0.392703 0.549098 0.055 Uiso 0.49(3) 1 calc R U P A 1
H9MC H 0.617168 0.390993 0.615107 0.055 Uiso 0.49(3) 1 calc R U P A 1
C10 C 0.5806(4) 0.53834(15) 0.55797(16) 0.0287(5) Uani 1 1 d D . . . .
H10 H 0.423566 0.524079 0.579794 0.034 Uiso 0.49(3) 1 calc R U P A 1
H10A H 0.412868 0.529471 0.570896 0.034 Uiso 0.51(3) 1 calc R U P A 2
O11 O 0.6255(3) 0.61978(10) 0.56157(12) 0.0272(4) Uani 1 1 d . . . . .
C12 C 0.6128(4) 0.65385(14) 0.65877(17) 0.0252(5) Uani 1 1 d . . . . .
H12 H 0.447267 0.648433 0.676408 0.030 Uiso 1 1 calc R U . . .
C12A C 0.7795(4) 0.61281(15) 0.73943(18) 0.0308(5) Uani 1 1 d D . . . .
O13 O 0.6624(3) 0.73378(10) 0.64844(14) 0.0370(4) Uani 1 1 d . . . . .
O14 O 0.6051(3) 0.51566(11) 0.45754(12) 0.0324(4) Uani 1 1 d . . . . .
C15 C 0.4086(4) 0.51556(14) 0.39217(17) 0.0279(5) Uani 1 1 d . . . . .
O16 O 0.2181(3) 0.53487(12) 0.41311(13) 0.0385(4) Uani 1 1 d . . . . .
C17 C 0.4573(4) 0.48372(18) 0.29208(18) 0.0344(6) Uani 1 1 d . . . . .
H17A H 0.324856 0.498857 0.241967 0.041 Uiso 1 1 calc R U . . .
H17B H 0.459535 0.425620 0.295928 0.041 Uiso 1 1 calc R U . . .
C18 C 0.6878(4) 0.51117(16) 0.25484(17) 0.0314(5) Uani 1 1 d . . . . .
H18A H 0.675611 0.567859 0.238539 0.038 Uiso 1 1 calc R U . . .
H18B H 0.818557 0.504285 0.308869 0.038 Uiso 1 1 calc R U . . .
C19 C 0.7438(4) 0.46665(15) 0.16415(17) 0.0276(5) Uani 1 1 d . . . . .
O20 O 0.6060(3) 0.41486(11) 0.12743(13) 0.0341(4) Uani 1 1 d . . . . .
O21 O 0.9377(3) 0.48469(13) 0.12982(13) 0.0402(5) Uani 1 1 d D . . . .
C1B C 0.966(3) 0.3082(9) -0.1470(15) 0.0244(18) Uani 0.456(5) 1 d D . P B 1
C2B C 0.8534(15) 0.2384(6) -0.1720(7) 0.0278(13) Uani 0.456(5) 1 d D . P B 1
H2B H 0.735131 0.219747 -0.133118 0.033 Uiso 0.456(5) 1 calc R U P B 1
C3B C 0.9092(15) 0.1957(5) -0.2517(6) 0.0326(14) Uani 0.456(5) 1 d D . P B 1
H3B H 0.823549 0.149107 -0.270308 0.039 Uiso 0.456(5) 1 calc R U P B 1
C4B C 1.094(3) 0.2202(11) -0.3072(12) 0.0345(11) Uani 0.456(5) 1 d D . P B 1
N4B N 1.156(3) 0.1758(11) -0.3850(9) 0.045(2) Uani 0.456(5) 1 d D . P B 1
H4BA H 1.270344 0.191401 -0.419353 0.054 Uiso 0.456(5) 1 calc R U P B 1
H4BB H 1.080784 0.131531 -0.400699 0.054 Uiso 0.456(5) 1 calc R U P B 1
C5B C 1.2074(15) 0.2909(4) -0.2791(6) 0.0370(12) Uani 0.456(5) 1 d D . P B 1
H5BA H 1.323369 0.310905 -0.318170 0.044 Uiso 0.456(5) 1 calc R U P B 1
C6B C 1.1555(13) 0.3322(5) -0.1963(6) 0.0338(11) Uani 0.456(5) 1 d D . P B 1
H6BA H 1.247779 0.376430 -0.173265 0.041 Uiso 0.456(5) 1 calc R U P B 1
C7B C 0.895(4) 0.350(2) -0.060(2) 0.0280(19) Uani 0.456(5) 1 d D . P B 1
O8B O 1.062(2) 0.3884(5) -0.0150(11) 0.0416(17) Uani 0.456(5) 1 d D . P B 1
O9B O 0.692(3) 0.3337(19) -0.030(2) 0.033(2) Uani 0.456(5) 1 d D . P B 1
C1C C 0.969(3) 0.2937(7) -0.1413(12) 0.0244(18) Uani 0.544(5) 1 d D . P B 2
C2C C 0.7937(12) 0.2457(5) -0.1956(5) 0.0278(13) Uani 0.544(5) 1 d D . P B 2
H2C H 0.641764 0.241290 -0.172953 0.033 Uiso 0.544(5) 1 calc R U P B 2
C3C C 0.8410(12) 0.2059(4) -0.2798(5) 0.0326(14) Uani 0.544(5) 1 d D . P B 2
H3C H 0.724024 0.172004 -0.312060 0.039 Uiso 0.544(5) 1 calc R U P B 2
C4C C 1.056(2) 0.2139(9) -0.3194(10) 0.0345(11) Uani 0.544(5) 1 d D . P B 2
N4C N 1.091(2) 0.1784(9) -0.4067(8) 0.045(2) Uani 0.544(5) 1 d D . P B 2
H4CA H 0.977856 0.150035 -0.438680 0.054 Uiso 0.544(5) 1 calc R U P B 2
H4CB H 1.227339 0.183598 -0.431372 0.054 Uiso 0.544(5) 1 calc R U P B 2
C5C C 1.2339(12) 0.2608(4) -0.2654(5) 0.0370(12) Uani 0.544(5) 1 d D . P B 2
H5C H 1.386245 0.264786 -0.287720 0.044 Uiso 0.544(5) 1 calc R U P B 2
C6C C 1.1846(11) 0.3004(4) -0.1809(5) 0.0338(11) Uani 0.544(5) 1 d D . P B 2
H6C H 1.302534 0.333573 -0.147969 0.041 Uiso 0.544(5) 1 calc R U P B 2
C7C C 0.920(3) 0.3447(16) -0.0576(19) 0.0280(19) Uani 0.544(5) 1 d D . P B 2
O8C O 1.0283(19) 0.4093(4) -0.0268(9) 0.0416(17) Uani 0.544(5) 1 d D . P B 2
O9C O 0.728(2) 0.3299(16) -0.0198(16) 0.033(2) Uani 0.544(5) 1 d D . P B 2
C9D C 0.738(3) 0.4890(7) 0.6303(8) 0.032(2) Uani 0.51(3) 1 d D . P A 2
H9D H 0.903928 0.495086 0.613976 0.039 Uiso 0.51(3) 1 calc R U P A 2
C9N C 0.667(3) 0.4014(5) 0.6158(7) 0.040(2) Uani 0.51(3) 1 d D . P A 2
H9NA H 0.495521 0.396078 0.616029 0.059 Uiso 0.51(3) 1 calc R U P A 2
H9NB H 0.747317 0.370108 0.670438 0.059 Uiso 0.51(3) 1 calc R U P A 2
H9NC H 0.713102 0.382618 0.551803 0.059 Uiso 0.51(3) 1 calc R U P A 2
C8E C 0.724(3) 0.5206(6) 0.7379(8) 0.029(2) Uani 0.51(3) 1 d D . P A 2
H8E H 0.854979 0.494779 0.781745 0.035 Uiso 0.51(3) 1 calc R U P A 2
C8D C 0.494(3) 0.4985(6) 0.7794(7) 0.030(2) Uani 0.51(3) 1 d D . P A 2
H8DA H 0.473029 0.440733 0.775751 0.036 Uiso 0.51(3) 1 calc R U P A 2
H8DB H 0.359734 0.522859 0.737529 0.036 Uiso 0.51(3) 1 calc R U P A 2
C7D C 0.489(3) 0.5251(6) 0.8879(8) 0.034(2) Uani 0.51(3) 1 d D . P A 2
H7DA H 0.610109 0.496245 0.932150 0.040 Uiso 0.51(3) 1 calc R U P A 2
H7DB H 0.332540 0.514601 0.910438 0.040 Uiso 0.51(3) 1 calc R U P A 2
H9B H 0.671(10) 0.358(3) 0.026(3) 0.13(2) Uiso 1 1 d D . . . .
H21 H 0.973(11) 0.455(3) 0.082(4) 0.14(2) Uiso 1 1 d D . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 O2 1.468(4) . ?
O1 C12A 1.453(3) . ?
O2 C3 1.405(4) . ?
C3 C3M 1.509(5) . ?
C3 C4 1.530(5) . ?
C3 O13 1.440(4) . ?
C3M H3MA 0.9800 . ?
C3M H3MB 0.9800 . ?
C3M H3MC 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.519(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C5A 1.530(4) . ?
C5A H5AA 1.0000 . ?
C5A C6 1.526(4) . ?
C5A C12A 1.552(3) . ?
C6 H6A 1.0000 . ?
C6 H6B 1.0000 . ?
C6 C6M 1.534(4) . ?
C6 C7 1.538(10) . ?
C6 C7D 1.540(10) . ?
C6M H6MA 0.9800 . ?
C6M H6MB 0.9800 . ?
C6M H6MC 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.529(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C8A 1.524(9) . ?
C8A H8AA 1.0000 . ?
C8A C9 1.532(11) . ?
C8A C12A 1.503(12) . ?
C9 H9 1.0000 . ?
C9 C9M 1.532(11) . ?
C9 C10 1.543(11) . ?
C9M H9MA 0.9800 . ?
C9M H9MB 0.9800 . ?
C9M H9MC 0.9800 . ?
C10 H10 1.0000 . ?
C10 H10A 1.0000 . ?
C10 O11 1.409(3) . ?
C10 O14 1.426(3) . ?
C10 C9D 1.505(12) . ?
O11 C12 1.439(3) . ?
C12 H12 1.0000 . ?
C12 C12A 1.531(3) . ?
C12 O13 1.399(3) . ?
C12A C8E 1.600(11) . ?
O14 C15 1.347(3) . ?
C15 O16 1.196(3) . ?
C15 C17 1.504(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.527(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.498(3) . ?
C19 O20 1.246(3) . ?
C19 O21 1.278(3) . ?
O21 H21 0.86(3) . ?
C1B C2B 1.374(12) . ?
C1B C6B 1.386(11) . ?
C1B C7B 1.461(13) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.360(10) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.417(12) . ?
C4B N4B 1.365(12) . ?
C4B C5B 1.398(12) . ?
N4B H4BA 0.8800 . ?
N4B H4BB 0.8800 . ?
C5B H5BA 0.9500 . ?
C5B C6B 1.375(9) . ?
C6B H6BA 0.9500 . ?
C7B O8B 1.254(17) . ?
C7B O9B 1.291(12) . ?
O9B H9B 0.88(3) . ?
C1C C2C 1.427(11) . ?
C1C C6C 1.395(10) . ?
C1C C7C 1.471(10) . ?
C2C H2C 0.9500 . ?
C2C C3C 1.371(8) . ?
C3C H3C 0.9500 . ?
C3C C4C 1.392(9) . ?
C4C N4C 1.354(9) . ?
C4C C5C 1.427(10) . ?
N4C H4CA 0.8800 . ?
N4C H4CB 0.8800 . ?
C5C H5C 0.9500 . ?
C5C C6C 1.375(8) . ?
C6C H6C 0.9500 . ?
C7C O8C 1.306(14) . ?
C7C O9C 1.279(11) . ?
O9C H9B 0.86(3) . ?
C9D H9D 1.0000 . ?
C9D C9N 1.551(11) . ?
C9D C8E 1.552(10) . ?
C9N H9NA 0.9800 . ?
C9N H9NB 0.9800 . ?
C9N H9NC 0.9800 . ?
C8E H8E 1.0000 . ?
C8E C8D 1.528(9) . ?
C8D H8DA 0.9900 . ?
C8D H8DB 0.9900 . ?
C8D C7D 1.530(9) . ?
C7D H7DA 0.9900 . ?
C7D H7DB 0.9900 . ?

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
C12A O1 O2 111.79(18) . . ?
C3 O2 O1 108.4(2) . . ?
O2 C3 C3M 103.1(3) . . ?
O2 C3 C4 113.6(3) . . ?
O2 C3 O13 107.9(2) . . ?
C3M C3 C4 114.0(3) . . ?
O13 C3 C3M 107.8(3) . . ?
O13 C3 C4 110.0(2) . . ?
C3 C3M H3MA 109.5 . . ?
C3 C3M H3MB 109.5 . . ?
C3 C3M H3MC 109.5 . . ?
H3MA C3M H3MB 109.5 . . ?
H3MA C3M H3MC 109.5 . . ?
H3MB C3M H3MC 109.5 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.2(2) . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C4 C5 H5A 108.3 . . ?
C4 C5 H5B 108.3 . . ?
C4 C5 C5A 115.7(2) . . ?
H5A C5 H5B 107.4 . . ?
C5A C5 H5A 108.3 . . ?
C5A C5 H5B 108.3 . . ?
C5 C5A H5AA 106.4 . . ?
C5 C5A C12A 112.4(2) . . ?
C6 C5A C5 110.8(2) . . ?
C6 C5A H5AA 106.4 . . ?
C6 C5A C12A 113.7(2) . . ?
C12A C5A H5AA 106.4 . . ?
C5A C6 H6A 110.2 . . ?
C5A C6 H6B 105.7 . . ?
C5A C6 C6M 111.9(2) . . ?
C5A C6 C7 103.3(5) . . ?
C5A C6 C7D 119.0(6) . . ?
C6M C6 H6A 110.2 . . ?
C6M C6 H6B 105.7 . . ?
C6M C6 C7 110.9(4) . . ?
C6M C6 C7D 107.8(4) . . ?
C7 C6 H6A 110.2 . . ?
C7D C6 H6B 105.7 . . ?
C6 C6M H6MA 109.5 . . ?
C6 C6M H6MB 109.5 . . ?
C6 C6M H6MC 109.5 . . ?
H6MA C6M H6MB 109.5 . . ?
H6MA C6M H6MC 109.5 . . ?
H6MB C6M H6MC 109.5 . . ?
C6 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C6 114.6(8) . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C8A C8 C7 111.5(7) . . ?
C8A C8 H8A 109.3 . . ?
C8A C8 H8B 109.3 . . ?
C8 C8A H8AA 106.7 . . ?
C8 C8A C9 115.5(8) . . ?
C9 C8A H8AA 106.7 . . ?
C12A C8A C8 108.8(8) . . ?
C12A C8A H8AA 106.7 . . ?
C12A C8A C9 111.9(9) . . ?
C8A C9 H9 109.0 . . ?
C8A C9 C9M 110.9(8) . . ?
C8A C9 C10 106.7(8) . . ?
C9M C9 H9 109.0 . . ?
C9M C9 C10 112.1(9) . . ?
C10 C9 H9 109.0 . . ?
C9 C9M H9MA 109.5 . . ?
C9 C9M H9MB 109.5 . . ?
C9 C9M H9MC 109.5 . . ?
H9MA C9M H9MB 109.5 . . ?
H9MA C9M H9MC 109.5 . . ?
H9MB C9M H9MC 109.5 . . ?
C9 C10 H10 113.2 . . ?
O11 C10 C9 106.6(5) . . ?
O11 C10 H10 113.2 . . ?
O11 C10 H10A 108.4 . . ?
O11 C10 O14 105.24(18) . . ?
O11 C10 C9D 115.7(5) . . ?
O14 C10 C9 104.8(4) . . ?
O14 C10 H10 113.2 . . ?
O14 C10 H10A 108.4 . . ?
O14 C10 C9D 110.5(5) . . ?
C9D C10 H10A 108.4 . . ?
C10 O11 C12 113.63(17) . . ?
O11 C12 H12 108.6 . . ?
O11 C12 C12A 111.83(18) . . ?
C12A C12 H12 108.6 . . ?
O13 C12 O11 105.74(18) . . ?
O13 C12 H12 108.6 . . ?
O13 C12 C12A 113.4(2) . . ?
O1 C12A C5A 106.11(19) . . ?
O1 C12A C8A 97.5(6) . . ?
O1 C12A C12 110.1(2) . . ?
O1 C12A C8E 109.6(6) . . ?
C5A C12A C8E 108.8(4) . . ?
C8A C12A C5A 115.6(5) . . ?
C8A C12A C12 113.2(6) . . ?
C12 C12A C5A 112.87(19) . . ?
C12 C12A C8E 109.4(5) . . ?
C12 O13 C3 113.4(2) . . ?
C15 O14 C10 117.38(19) . . ?
O14 C15 C17 111.4(2) . . ?
O16 C15 O14 123.9(2) . . ?
O16 C15 C17 124.6(2) . . ?
C15 C17 H17A 108.4 . . ?
C15 C17 H17B 108.4 . . ?
C15 C17 C18 115.5(2) . . ?
H17A C17 H17B 107.5 . . ?
C18 C17 H17A 108.4 . . ?
C18 C17 H17B 108.4 . . ?
C17 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 C17 112.2(2) . . ?
C19 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
O20 C19 C18 120.0(2) . . ?
O20 C19 O21 123.9(2) . . ?
O21 C19 C18 116.1(2) . . ?
C19 O21 H21 114(4) . . ?
C2B C1B C6B 120.3(9) . . ?
C2B C1B C7B 116.9(12) . . ?
C6B C1B C7B 122.3(10) . . ?
C1B C2B H2B 119.6 . . ?
C3B C2B C1B 120.8(9) . . ?
C3B C2B H2B 119.6 . . ?
C2B C3B H3B 119.8 . . ?
C2B C3B C4B 120.5(9) . . ?
C4B C3B H3B 119.8 . . ?
N4B C4B C3B 120.4(11) . . ?
N4B C4B C5B 122.4(11) . . ?
C5B C4B C3B 117.2(9) . . ?
C4B N4B H4BA 120.0 . . ?
C4B N4B H4BB 120.0 . . ?
H4BA N4B H4BB 120.0 . . ?
C4B C5B H5BA 119.1 . . ?
C6B C5B C4B 121.8(8) . . ?
C6B C5B H5BA 119.1 . . ?
C1B C6B H6BA 120.6 . . ?
C5B C6B C1B 118.7(7) . . ?
C5B C6B H6BA 120.6 . . ?
O8B C7B C1B 112.4(14) . . ?
O8B C7B O9B 128.2(16) . . ?
O9B C7B C1B 118.5(13) . . ?
C7B O9B H9B 112(4) . . ?
C2C C1C C7C 123.5(10) . . ?
C6C C1C C2C 116.5(8) . . ?
C6C C1C C7C 119.3(9) . . ?
C1C C2C H2C 119.4 . . ?
C3C C2C C1C 121.2(7) . . ?
C3C C2C H2C 119.4 . . ?
C2C C3C H3C 119.1 . . ?
C2C C3C C4C 121.7(7) . . ?
C4C C3C H3C 119.1 . . ?
C3C C4C C5C 117.8(7) . . ?
N4C C4C C3C 120.3(9) . . ?
N4C C4C C5C 121.9(9) . . ?
C4C N4C H4CA 120.0 . . ?
C4C N4C H4CB 120.0 . . ?
H4CA N4C H4CB 120.0 . . ?
C4C C5C H5C 120.1 . . ?
C6C C5C C4C 119.9(6) . . ?
C6C C5C H5C 120.1 . . ?
C1C C6C H6C 118.6 . . ?
C5C C6C C1C 122.8(7) . . ?
C5C C6C H6C 118.6 . . ?
O8C C7C C1C 128.2(13) . . ?
O9C C7C C1C 115.2(11) . . ?
O9C C7C O8C 115.7(13) . . ?
C7C O9C H9B 125(5) . . ?
C10 C9D H9D 108.1 . . ?
C10 C9D C9N 109.0(8) . . ?
C10 C9D C8E 108.9(8) . . ?
C9N C9D H9D 108.1 . . ?
C9N C9D C8E 114.3(7) . . ?
C8E C9D H9D 108.1 . . ?
C9D C9N H9NA 109.5 . . ?
C9D C9N H9NB 109.5 . . ?
C9D C9N H9NC 109.5 . . ?
H9NA C9N H9NB 109.5 . . ?
H9NA C9N H9NC 109.5 . . ?
H9NB C9N H9NC 109.5 . . ?
C12A C8E H8E 106.9 . . ?
C9D C8E C12A 108.8(7) . . ?
C9D C8E H8E 106.9 . . ?
C8D C8E C12A 114.3(8) . . ?
C8D C8E C9D 112.6(8) . . ?
C8D C8E H8E 106.9 . . ?
C8E C8D H8DA 109.2 . . ?
C8E C8D H8DB 109.2 . . ?
C8E C8D C7D 112.2(7) . . ?
H8DA C8D H8DB 107.9 . . ?
C7D C8D H8DA 109.2 . . ?
C7D C8D H8DB 109.2 . . ?
C6 C7D H7DA 110.2 . . ?
C6 C7D H7DB 110.2 . . ?
C8D C7D C6 107.7(7) . . ?
C8D C7D H7DA 110.2 . . ?
C8D C7D H7DB 110.2 . . ?
H7DA C7D H7DB 108.5 . . ?

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
O1 O2 C3 C3M 171.7(3) . . . . ?
O1 O2 C3 C4 47.9(3) . . . . ?
O1 O2 C3 O13 -74.4(3) . . . . ?
O1 C12A C8E C9D -66.4(9) . . . . ?
O1 C12A C8E C8D 166.7(6) . . . . ?
O2 O1 C12A C5A -106.5(2) . . . . ?
O2 O1 C12A C8A 134.1(5) . . . . ?
O2 O1 C12A C12 15.9(3) . . . . ?
O2 O1 C12A C8E 136.2(5) . . . . ?
O2 C3 C4 C5 -94.8(3) . . . . ?
O2 C3 O13 C12 35.0(3) . . . . ?
C3 C4 C5 C5A 57.8(4) . . . . ?
C3M C3 C4 C5 147.5(3) . . . . ?
C3M C3 O13 C12 145.7(2) . . . . ?
C4 C3 O13 C12 -89.4(3) . . . . ?
C4 C5 C5A C6 -168.1(3) . . . . ?
C4 C5 C5A C12A -39.6(3) . . . . ?
C5 C5A C6 C6M -57.7(3) . . . . ?
C5 C5A C6 C7 -177.2(5) . . . . ?
C5 C5A C6 C7D 175.3(6) . . . . ?
C5 C5A C12A O1 71.6(3) . . . . ?
C5 C5A C12A C8A 178.5(6) . . . . ?
C5 C5A C12A C12 -49.0(3) . . . . ?
C5 C5A C12A C8E -170.6(6) . . . . ?
C5A C6 C7 C8 -60.4(7) . . . . ?
C5A C6 C7D C8D -50.7(8) . . . . ?
C5A C12A C8E C9D 178.0(7) . . . . ?
C5A C12A C8E C8D 51.1(9) . . . . ?
C6 C5A C12A O1 -161.4(2) . . . . ?
C6 C5A C12A C8A -54.6(7) . . . . ?
C6 C5A C12A C12 78.0(3) . . . . ?
C6 C5A C12A C8E -43.6(6) . . . . ?
C6 C7 C8 C8A 61.6(10) . . . . ?
C6M C6 C7 C8 179.5(5) . . . . ?
C6M C6 C7D C8D -179.5(5) . . . . ?
C7 C8 C8A C9 -177.7(9) . . . . ?
C7 C8 C8A C12A -50.9(11) . . . . ?
C8 C8A C9 C9M -53.0(13) . . . . ?
C8 C8A C9 C10 69.3(11) . . . . ?
C8 C8A C12A O1 160.6(7) . . . . ?
C8 C8A C12A C5A 48.7(10) . . . . ?
C8 C8A C12A C12 -83.7(8) . . . . ?
C8A C9 C10 O11 65.9(8) . . . . ?
C8A C9 C10 O14 177.2(6) . . . . ?
C9 C8A C12A O1 -70.6(9) . . . . ?
C9 C8A C12A C5A 177.5(7) . . . . ?
C9 C8A C12A C12 45.1(10) . . . . ?
C9 C10 O11 C12 -68.1(5) . . . . ?
C9 C10 O14 C15 155.3(6) . . . . ?
C9M C9 C10 O11 -172.5(6) . . . . ?
C9M C9 C10 O14 -61.3(7) . . . . ?
C10 O11 C12 C12A 55.9(2) . . . . ?
C10 O11 C12 O13 179.78(18) . . . . ?
C10 O14 C15 O16 1.7(4) . . . . ?
C10 O14 C15 C17 -175.0(2) . . . . ?
C10 C9D C8E C12A -52.8(10) . . . . ?
C10 C9D C8E C8D 75.0(10) . . . . ?
O11 C10 O14 C15 -92.5(2) . . . . ?
O11 C10 C9D C9N -179.4(5) . . . . ?
O11 C10 C9D C8E 55.2(8) . . . . ?
O11 C12 C12A O1 65.4(2) . . . . ?
O11 C12 C12A C5A -176.3(2) . . . . ?
O11 C12 C12A C8A -42.6(6) . . . . ?
O11 C12 C12A C8E -55.1(5) . . . . ?
O11 C12 O13 C3 -95.7(2) . . . . ?
C12 C12A C8E C9D 54.3(9) . . . . ?
C12 C12A C8E C8D -72.6(8) . . . . ?
C12A O1 O2 C3 45.1(3) . . . . ?
C12A C5A C6 C6M 174.5(2) . . . . ?
C12A C5A C6 C7 55.1(5) . . . . ?
C12A C5A C6 C7D 47.5(6) . . . . ?
C12A C8A C9 C9M -178.2(9) . . . . ?
C12A C8A C9 C10 -55.9(10) . . . . ?
C12A C12 O13 C3 27.1(3) . . . . ?
C12A C8E C8D C7D -58.9(11) . . . . ?
O13 C3 C4 C5 26.3(4) . . . . ?
O13 C12 C12A O1 -54.1(3) . . . . ?
O13 C12 C12A C5A 64.3(3) . . . . ?
O13 C12 C12A C8A -162.0(5) . . . . ?
O13 C12 C12A C8E -174.5(5) . . . . ?
O14 C10 O11 C12 -179.04(17) . . . . ?
O14 C10 C9D C9N -60.0(8) . . . . ?
O14 C10 C9D C8E 174.6(6) . . . . ?
O14 C15 C17 C18 -41.8(3) . . . . ?
C15 C17 C18 C19 170.1(2) . . . . ?
O16 C15 C17 C18 141.6(3) . . . . ?
C17 C18 C19 O20 1.0(3) . . . . ?
C17 C18 C19 O21 -178.2(2) . . . . ?
C1B C2B C3B C4B 4(2) . . . . ?
C2B C1B C6B C5B 9(3) . . . . ?
C2B C1B C7B O8B 149(3) . . . . ?
C2B C1B C7B O9B -21(4) . . . . ?
C2B C3B C4B N4B 177.6(14) . . . . ?
C2B C3B C4B C5B -3(2) . . . . ?
C3B C4B C5B C6B 5(2) . . . . ?
C4B C5B C6B C1B -8(2) . . . . ?
N4B C4B C5B C6B -175.3(13) . . . . ?
C6B C1B C2B C3B -7(3) . . . . ?
C6B C1B C7B O8B -24(5) . . . . ?
C6B C1B C7B O9B 167(3) . . . . ?
C7B C1B C2B C3B -180(2) . . . . ?
C7B C1B C6B C5B -179(2) . . . . ?
C1C C2C C3C C4C -3.7(17) . . . . ?
C2C C1C C6C C5C -3(2) . . . . ?
C2C C1C C7C O8C -153(3) . . . . ?
C2C C1C C7C O9C 16(4) . . . . ?
C2C C3C C4C N4C -175.2(11) . . . . ?
C2C C3C C4C C5C 4.4(19) . . . . ?
C3C C4C C5C C6C -4.2(19) . . . . ?
C4C C5C C6C C1C 3.4(16) . . . . ?
N4C C4C C5C C6C 175.4(12) . . . . ?
C6C C1C C2C C3C 3(2) . . . . ?
C6C C1C C7C O8C 17(4) . . . . ?
C6C C1C C7C O9C -174(2) . . . . ?
C7C C1C C2C C3C 172.8(19) . . . . ?
C7C C1C C6C C5C -173.1(19) . . . . ?
C9D C10 O11 C12 -56.8(6) . . . . ?
C9D C10 O14 C15 141.9(6) . . . . ?
C9D C8E C8D C7D 176.2(9) . . . . ?
C9N C9D C8E C12A -175.1(9) . . . . ?
C9N C9D C8E C8D -47.2(12) . . . . ?
C8E C8D C7D C6 54.4(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.255
_oxdiff_exptl_absorpt_empirical_full_min 0.793
####################################################################### 
# 
# 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_twin
_database_code_depnum_ccdc_archive 'CCDC 2427258'
loop_
_audit_author_name
_audit_author_address
'Laszlo Fabian'
;University of East Anglia
United Kingdom
;
_audit_update_record             
;
2025-10-07 deposited with the CCDC.	2025-10-15 downloaded from the CCDC.
;
_audit_creation_date             2025-09-17
_audit_creation_method           
; 
Olex2 1.5 
(compiled 2025.07.13 svn.rb7424ae for OlexSys, GUI svn.r7314) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'artesunate urea acetonitrile solvate'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H28 O8, C H4 N2 O, C2 H3 N'
_chemical_formula_sum            'C22 H35 N3 O9'
_chemical_formula_weight         485.53
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H35 N3 O9'
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           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                   10.5562(3)
_cell_length_b                   7.3837(2)
_cell_length_c                   15.7892(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.315(3)
_cell_angle_gamma                90
_cell_volume                     1217.73(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5829
_cell_measurement_temperature    99.99(11)
_cell_measurement_theta_max      73.2760
_cell_measurement_theta_min      4.2120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.1675
-1 0 0 0.1250
0 1 -2 0.0703
0 -1 2 0.0718
-1 -2 -2 0.0706
0 1 2 0.0690
2 2 -1 0.1068
2 -1 -2 0.1389
-2 -1 2 0.1142
2 -2 -1 0.1005
0 1 0 0.0616
1 -2 -2 0.0819
-1 -2 2 0.0728
1 0 -2 0.1417
0 0 -1 0.0938
0 0 1 0.0700
1 0 2 0.1193
0 -2 -1 0.0741
-1 0 -2 0.1080

_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.142
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0005 0.0044 -0.0174 -0.1257 0.0153 0.0754
-1.0005 -0.0044 0.0174 0.1257 -0.0153 -0.0754
-0.0095 1.0048 -1.9686 0.1711 0.0409 0.2254
0.0095 -1.0048 1.9686 -0.1711 -0.0409 -0.2254
-0.9959 -1.9810 -2.0658 0.0599 -0.4648 -0.1506
0.0001 0.9828 2.0450 -0.0132 0.2860 -0.0250
1.9893 2.0018 -0.9618 -0.0474 0.2962 0.4139
2.0009 -0.9741 -2.0798 -0.2382 -0.2554 0.1758
-1.9915 -1.0135 2.0034 0.0803 -0.0715 -0.3762
2.0080 -1.9734 -1.1146 -0.3632 -0.3576 0.0130
-0.0047 0.9938 0.0382 0.0789 0.1635 0.1002
1.0051 -1.9723 -2.1006 -0.1914 -0.4341 0.0002
-0.9863 -2.0030 1.9478 -0.1243 -0.2197 -0.4011
0.9957 0.0154 -2.0242 -0.0335 -0.1072 0.2006
-0.0024 0.0055 -1.0034 0.0461 -0.0613 0.0626
0.0024 -0.0055 1.0034 -0.0461 0.0613 -0.0626
1.0053 -0.0066 1.9894 -0.2178 0.1379 -0.0498
0.0070 -1.9821 -1.0798 -0.1118 -0.3882 -0.1378
-1.0053 0.0066 -1.9894 0.2178 -0.1379 0.0498

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7863
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.433
_diffrn_reflns_theta_min         2.828
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details      
; 
List of Runs (angles in degrees, time in seconds): 
  
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames 
#-------------------------------------------------------------------------- 
  1  ω    -61.00 -20.00   0.50    0.95    --  -46.79  82.00 -54.00   82 
  2  ω    -16.00  26.00   0.50    0.95    --  -46.79  82.00 -54.00   84 
  3  ω    -20.00  56.00   0.50    0.95    --   46.79 -82.00-176.00  152 
  4  ω   -148.00-122.00   0.50    3.82    --  -91.75 -82.00-176.00   52 
  5  ω    -73.00 -27.00   0.50    3.82    --  -91.75  82.00 -54.00   92 
  6  ω    118.00 158.00   0.50    3.82    --  106.64  82.00 -54.00   80 
  7  ω    -40.00  25.00   0.50    0.95    --  -46.79  37.00-150.00  130 
  8  ω    -24.00  17.00   0.50    0.95    --  -46.79  19.00 -90.00   82 
  9  ω    -11.00  14.00   0.50    0.95    --   46.79 -19.00-120.00   50 
 10  ω    -16.00  11.00   0.50    0.95    --   46.79 -19.00 -60.00   54 
 11  ω    -24.00  12.00   0.50    0.95    --   46.79 -19.00-180.00   72 
 12  ω     -1.00  77.00   0.50    0.95    --   46.79 -99.00   0.00  156 
 13  ω   -135.00-103.00   0.50    3.82    --  -91.75 -45.00  60.00   64 
 14  ω   -137.00 -79.00   0.50    3.82    --  -91.75 -45.00-150.00  116 
 15  ω   -148.00 -79.00   0.50    3.82    --  -91.75 -45.00  90.00  138 
 16  ω   -162.00-109.00   0.50    3.82    --  -91.75 -61.00  60.00  106 
 17  ω    -50.00 -23.00   0.50    3.82    --  -91.75  45.00  90.00   54 
 18  ω    -51.00 -25.00   0.50    3.82    --  -91.75  45.00-120.00   52 
 19  ω    -49.00 -24.00   0.50    3.82    --  -91.75  45.00  60.00   50 
 20  ω   -157.00 -81.00   0.50    3.82    --  -91.75 -45.00-180.00  152 
 21  ω   -107.00 -82.00   0.50    3.82    --  -91.75 -30.00-120.00   50 
 22  ω    -70.00 -41.00   0.50    3.82    --  -91.75  61.00 -90.00   58 
 23  ω   -164.00-137.00   0.50    3.82    --  -91.75 -30.00-120.00   54 
 24  ω   -162.00-120.00   0.50    3.82    --  -91.75 -61.00 -90.00   84 
 25  ω   -154.00-100.00   0.50    3.82    --  -91.75 -61.00 150.00  108 
 26  ω    -48.00 -23.00   0.50    3.82    --  -91.75  45.00 150.00   50 
 27  ω   -153.00-103.00   0.50    3.82    --  -91.75 -94.00 150.00  100 
 28  ω    -50.00 -24.00   0.50    3.82    --  -91.75  45.00 -30.00   52 
 29  ω   -162.00-104.00   0.50    3.82    --  -91.75 -61.00-150.00  116 
 30  ω   -152.00 -99.00   0.50    3.82    --  -91.75 -61.00  90.00  106 
 31  ω     38.00 109.00   0.50    3.82    --  106.64-125.00  30.00  142 
 32  ω     34.00  71.00   0.50    3.82    --  106.64 -61.00 -30.00   74 
 33  ω     37.00 111.00   0.50    3.82    --  106.64-125.00 -60.00  148 
 34  ω    105.00 172.00   0.50    3.82    --  106.64  61.00   0.00  134 
 35  ω     36.00  62.00   0.50    3.82    --  106.64 -61.00  60.00   52 
 36  ω    106.00 133.00   0.50    3.82    --  106.64  45.00-120.00   54 
 37  ω    137.00 171.00   0.50    3.82    --  106.64  45.00-120.00   68 
 38  ω     35.00 101.00   0.50    3.82    --  106.64 -82.00-176.00  132 
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1267303000
_diffrn_orient_matrix_UB_12      0.0805767000
_diffrn_orient_matrix_UB_13      -0.0451546000
_diffrn_orient_matrix_UB_21      0.0156719000
_diffrn_orient_matrix_UB_22      0.1621641000
_diffrn_orient_matrix_UB_23      0.0619203000
_diffrn_orient_matrix_UB_31      0.0738331000
_diffrn_orient_matrix_UB_32      0.1035830000
_diffrn_orient_matrix_UB_33      -0.0620022000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.831
_reflns_number_gt                7230
_reflns_number_total             7863
_reflns_special_details          
; 
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 42.92a 64-bit (release 29-05-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         7863
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0659
_refine_ls_restrained_S_all      1.100
_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)+(0.0986P)²+0.8811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1891
_refine_ls_wR_factor_ref         0.1972
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
; 
1. Twinned data refinement 
 Scales: 0.448(3) 
 0.552(3) 
2. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All N(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
3.a Ternary CH refined with riding coordinates: 
 C5A(H5AA), C6(H6), C8A(H8AA), C9(H9), C10(H10), C12(H12) 
3.b Secondary CH2 refined with riding coordinates: 
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C17(H17A,H17B), C18(H18A, 
 H18B) 
3.c X=CH2 refined with riding coordinates: 
 N1U(H1UA,H1UB), N3U(H3UA,H3UB) 
3.d Idealised Me refined as rotating group: 
 C3M(H3MA,H3MB,H3MC), C6M(H6MA,H6MB,H6MC), C9M(H9MA,H9MB,H9MC), C1S(H1SA,H1SB, 
 H1SC) 
3.e Idealised tetrahedral OH refined as rotating group: 
 O21(H21) 
;
_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
O1 O 0.7470(4) 0.3483(5) 0.8687(2) 0.0340(8) Uani 1 1 d . . . . .
O2 O 0.7232(4) 0.2293(5) 0.7933(2) 0.0364(8) Uani 1 1 d . . . . .
C3 C 0.8095(5) 0.2742(8) 0.7357(3) 0.0376(12) Uani 1 1 d . . . . .
C3M C 0.7900(6) 0.1294(9) 0.6679(4) 0.0447(14) Uani 1 1 d . . . . .
H3MA H 0.698345 0.116687 0.647139 0.067 Uiso 1 1 calc R U . . .
H3MB H 0.823695 0.014069 0.692331 0.067 Uiso 1 1 calc R U . . .
H3MC H 0.835164 0.163142 0.620258 0.067 Uiso 1 1 calc R U . . .
C4 C 0.9481(6) 0.2884(9) 0.7802(4) 0.0407(13) Uani 1 1 d . . . . .
H4A H 0.958497 0.210036 0.831590 0.049 Uiso 1 1 calc R U . . .
H4B H 1.005670 0.241629 0.741003 0.049 Uiso 1 1 calc R U . . .
C5 C 0.9894(5) 0.4794(9) 0.8070(4) 0.0400(13) Uani 1 1 d . . . . .
H5A H 0.987051 0.553966 0.754676 0.048 Uiso 1 1 calc R U . . .
H5B H 1.079492 0.474956 0.835041 0.048 Uiso 1 1 calc R U . . .
C5A C 0.9105(5) 0.5755(8) 0.8673(3) 0.0342(12) Uani 1 1 d . . . . .
H5AA H 0.937690 0.523955 0.925668 0.041 Uiso 1 1 calc R U . . .
C6 C 0.9418(5) 0.7791(8) 0.8729(3) 0.0364(12) Uani 1 1 d . . . . .
H6 H 0.916471 0.832675 0.814792 0.044 Uiso 1 1 calc R U . . .
C6M C 1.0849(6) 0.8139(9) 0.8993(4) 0.0435(14) Uani 1 1 d . . . . .
H6MA H 1.113483 0.755658 0.954544 0.065 Uiso 1 1 calc R U . . .
H6MB H 1.100287 0.944645 0.904420 0.065 Uiso 1 1 calc R U . . .
H6MC H 1.132616 0.763843 0.855904 0.065 Uiso 1 1 calc R U . . .
C7 C 0.8635(6) 0.8725(8) 0.9342(4) 0.0391(12) Uani 1 1 d . . . . .
H7A H 0.888031 0.822797 0.992535 0.047 Uiso 1 1 calc R U . . .
H7B H 0.883352 1.003578 0.936159 0.047 Uiso 1 1 calc R U . . .
C8 C 0.7206(5) 0.8463(8) 0.9071(4) 0.0378(12) Uani 1 1 d . . . . .
H8A H 0.694689 0.905272 0.850984 0.045 Uiso 1 1 calc R U . . .
H8B H 0.673349 0.905403 0.949354 0.045 Uiso 1 1 calc R U . . .
C8A C 0.6847(5) 0.6456(8) 0.9004(3) 0.0335(11) Uani 1 1 d . . . . .
H8AA H 0.704116 0.594532 0.959480 0.040 Uiso 1 1 calc R U . . .
C9 C 0.5389(5) 0.6152(8) 0.8709(3) 0.0343(11) Uani 1 1 d . . . . .
H9 H 0.521080 0.483289 0.877484 0.041 Uiso 1 1 calc R U . . .
C9M C 0.4532(5) 0.7199(9) 0.9235(4) 0.0418(13) Uani 1 1 d . . . . .
H9MA H 0.482616 0.700443 0.984598 0.063 Uiso 1 1 calc R U . . .
H9MB H 0.364741 0.677275 0.909367 0.063 Uiso 1 1 calc R U . . .
H9MC H 0.457116 0.849373 0.910453 0.063 Uiso 1 1 calc R U . . .
C10 C 0.5128(5) 0.6592(7) 0.7761(3) 0.0320(11) Uani 1 1 d . . . . .
H10 H 0.537151 0.787477 0.766091 0.038 Uiso 1 1 calc R U . . .
O11 O 0.5808(4) 0.5401(5) 0.7290(2) 0.0328(8) Uani 1 1 d . . . . .
C12 C 0.7176(5) 0.5632(7) 0.7493(3) 0.0312(11) Uani 1 1 d . . . . .
H12 H 0.739220 0.689372 0.733341 0.037 Uiso 1 1 calc R U . . .
C12A C 0.7648(6) 0.5374(7) 0.8445(4) 0.0342(11) Uani 1 1 d . . . . .
O13 O 0.7698(4) 0.4433(5) 0.6951(2) 0.0344(8) Uani 1 1 d . . . . .
O14 O 0.3800(3) 0.6317(5) 0.7460(2) 0.0350(8) Uani 1 1 d . . . . .
C15 C 0.3346(5) 0.7048(7) 0.6692(3) 0.0338(11) Uani 1 1 d . . . . .
O16 O 0.4022(3) 0.7769(6) 0.6229(2) 0.0382(9) Uani 1 1 d . . . . .
C17 C 0.1917(5) 0.6943(9) 0.6521(4) 0.0373(12) Uani 1 1 d . . . . .
H17A H 0.155165 0.775161 0.692367 0.045 Uiso 1 1 calc R U . . .
H17B H 0.164371 0.568991 0.662519 0.045 Uiso 1 1 calc R U . . .
C18 C 0.1392(5) 0.7485(10) 0.5607(4) 0.0426(13) Uani 1 1 d . . . . .
H18A H 0.174596 0.868002 0.548118 0.051 Uiso 1 1 calc R U . . .
H18B H 0.167621 0.659165 0.520647 0.051 Uiso 1 1 calc R U . . .
C19 C -0.0047(5) 0.7584(8) 0.5463(3) 0.0367(12) Uani 1 1 d . . . . .
O20 O -0.0701(4) 0.7515(6) 0.6032(2) 0.0415(9) Uani 1 1 d . . . . .
O21 O -0.0506(4) 0.7794(8) 0.4650(2) 0.0506(12) Uani 1 1 d . . . . .
H21 H -0.130908 0.783389 0.459288 0.076 Uiso 1 1 calc R U . . .
N1U N -0.3476(4) 0.7439(7) 0.5547(3) 0.0392(11) Uani 1 1 d . . . . .
H1UA H -0.267423 0.719550 0.575311 0.047 Uiso 1 1 calc R U . . .
H1UB H -0.408696 0.722692 0.585784 0.047 Uiso 1 1 calc R U . . .
C2U C -0.3761(5) 0.8123(7) 0.4769(3) 0.0339(11) Uani 1 1 d . . . . .
N3U N -0.5006(5) 0.8452(8) 0.4480(3) 0.0418(11) Uani 1 1 d . . . . .
H3UA H -0.523208 0.889576 0.396341 0.050 Uiso 1 1 calc R U . . .
H3UB H -0.559236 0.822273 0.480950 0.050 Uiso 1 1 calc R U . . .
O4U O -0.2928(4) 0.8451(6) 0.4299(3) 0.0436(10) Uani 1 1 d . . . . .
C1S C -0.3971(7) 0.6684(10) 0.2433(4) 0.0502(15) Uani 1 1 d . . . . .
H1SA H -0.489187 0.685672 0.225634 0.075 Uiso 1 1 calc R U . . .
H1SB H -0.367625 0.748183 0.291714 0.075 Uiso 1 1 calc R U . . .
H1SC H -0.380432 0.542041 0.260341 0.075 Uiso 1 1 calc R U . . .
C2S C -0.3290(6) 0.7118(8) 0.1722(4) 0.0431(14) Uani 1 1 d . . . . .
N3S N -0.2771(6) 0.7478(11) 0.1161(4) 0.0599(16) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 O2 1.473(5) . ?
O1 C12A 1.467(7) . ?
O2 C3 1.417(7) . ?
C3 C3M 1.505(9) . ?
C3 C4 1.532(8) . ?
C3 O13 1.438(7) . ?
C3M H3MA 0.9800 . ?
C3M H3MB 0.9800 . ?
C3M H3MC 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.518(9) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C5A 1.527(8) . ?
C5A H5AA 1.0000 . ?
C5A C6 1.539(8) . ?
C5A C12A 1.554(7) . ?
C6 H6 1.0000 . ?
C6 C6M 1.529(8) . ?
C6 C7 1.525(8) . ?
C6M H6MA 0.9800 . ?
C6M H6MB 0.9800 . ?
C6M H6MC 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.520(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C8A 1.529(8) . ?
C8A H8AA 1.0000 . ?
C8A C9 1.558(7) . ?
C8A C12A 1.533(8) . ?
C9 H9 1.0000 . ?
C9 C9M 1.525(8) . ?
C9 C10 1.517(7) . ?
C9M H9MA 0.9800 . ?
C9M H9MB 0.9800 . ?
C9M H9MC 0.9800 . ?
C10 H10 1.0000 . ?
C10 O11 1.413(6) . ?
C10 O14 1.428(6) . ?
O11 C12 1.444(6) . ?
C12 H12 1.0000 . ?
C12 C12A 1.525(7) . ?
C12 O13 1.399(6) . ?
O14 C15 1.350(6) . ?
C15 O16 1.215(7) . ?
C15 C17 1.496(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.522(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.504(7) . ?
C19 O20 1.212(7) . ?
C19 O21 1.314(7) . ?
O21 H21 0.8400 . ?
N1U H1UA 0.8800 . ?
N1U H1UB 0.8800 . ?
N1U C2U 1.322(7) . ?
C2U N3U 1.350(7) . ?
C2U O4U 1.254(7) . ?
N3U H3UA 0.8800 . ?
N3U H3UB 0.8800 . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C1S C2S 1.452(10) . ?
C2S N3S 1.139(9) . ?

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
C12A O1 O2 111.7(4) . . ?
C3 O2 O1 109.2(4) . . ?
O2 C3 C3M 104.8(5) . . ?
O2 C3 C4 112.5(4) . . ?
O2 C3 O13 108.4(4) . . ?
C3M C3 C4 113.5(5) . . ?
O13 C3 C3M 107.4(4) . . ?
O13 C3 C4 110.0(5) . . ?
C3 C3M H3MA 109.5 . . ?
C3 C3M H3MB 109.5 . . ?
C3 C3M H3MC 109.5 . . ?
H3MA C3M H3MB 109.5 . . ?
H3MA C3M H3MC 109.5 . . ?
H3MB C3M H3MC 109.5 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.1(5) . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C4 C5 H5A 108.2 . . ?
C4 C5 H5B 108.2 . . ?
C4 C5 C5A 116.4(5) . . ?
H5A C5 H5B 107.3 . . ?
C5A C5 H5A 108.2 . . ?
C5A C5 H5B 108.2 . . ?
C5 C5A H5AA 106.7 . . ?
C5 C5A C6 110.9(5) . . ?
C5 C5A C12A 112.5(5) . . ?
C6 C5A H5AA 106.7 . . ?
C6 C5A C12A 112.8(4) . . ?
C12A C5A H5AA 106.7 . . ?
C5A C6 H6 107.8 . . ?
C6M C6 C5A 112.1(5) . . ?
C6M C6 H6 107.8 . . ?
C7 C6 C5A 110.3(5) . . ?
C7 C6 H6 107.8 . . ?
C7 C6 C6M 110.8(5) . . ?
C6 C6M H6MA 109.5 . . ?
C6 C6M H6MB 109.5 . . ?
C6 C6M H6MC 109.5 . . ?
H6MA C6M H6MB 109.5 . . ?
H6MA C6M H6MC 109.5 . . ?
H6MB C6M H6MC 109.5 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C6 111.8(4) . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C7 C8 C8A 111.6(5) . . ?
H8A C8 H8B 108.0 . . ?
C8A C8 H8A 109.3 . . ?
C8A C8 H8B 109.3 . . ?
C8 C8A H8AA 106.6 . . ?
C8 C8A C9 112.6(4) . . ?
C8 C8A C12A 113.2(5) . . ?
C9 C8A H8AA 106.6 . . ?
C12A C8A H8AA 106.6 . . ?
C12A C8A C9 110.9(4) . . ?
C8A C9 H9 107.6 . . ?
C9M C9 C8A 113.7(4) . . ?
C9M C9 H9 107.6 . . ?
C10 C9 C8A 107.1(4) . . ?
C10 C9 H9 107.6 . . ?
C10 C9 C9M 113.1(5) . . ?
C9 C9M H9MA 109.5 . . ?
C9 C9M H9MB 109.5 . . ?
C9 C9M H9MC 109.5 . . ?
H9MA C9M H9MB 109.5 . . ?
H9MA C9M H9MC 109.5 . . ?
H9MB C9M H9MC 109.5 . . ?
C9 C10 H10 110.2 . . ?
O11 C10 C9 110.6(4) . . ?
O11 C10 H10 110.2 . . ?
O11 C10 O14 106.6(4) . . ?
O14 C10 C9 109.1(4) . . ?
O14 C10 H10 110.2 . . ?
C10 O11 C12 112.2(4) . . ?
O11 C12 H12 108.1 . . ?
O11 C12 C12A 112.2(4) . . ?
C12A C12 H12 108.1 . . ?
O13 C12 O11 105.0(4) . . ?
O13 C12 H12 108.1 . . ?
O13 C12 C12A 115.0(4) . . ?
O1 C12A C5A 105.8(4) . . ?
O1 C12A C8A 104.1(4) . . ?
O1 C12A C12 109.9(4) . . ?
C8A C12A C5A 112.5(4) . . ?
C12 C12A C5A 112.2(4) . . ?
C12 C12A C8A 111.9(4) . . ?
C12 O13 C3 113.1(4) . . ?
C15 O14 C10 116.5(4) . . ?
O14 C15 C17 111.1(5) . . ?
O16 C15 O14 123.5(5) . . ?
O16 C15 C17 125.3(5) . . ?
C15 C17 H17A 109.2 . . ?
C15 C17 H17B 109.2 . . ?
C15 C17 C18 112.2(5) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C17 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 C17 112.2(5) . . ?
C19 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
O20 C19 C18 123.8(5) . . ?
O20 C19 O21 124.1(5) . . ?
O21 C19 C18 112.1(5) . . ?
C19 O21 H21 109.5 . . ?
H1UA N1U H1UB 120.0 . . ?
C2U N1U H1UA 120.0 . . ?
C2U N1U H1UB 120.0 . . ?
N1U C2U N3U 117.5(5) . . ?
O4U C2U N1U 122.6(5) . . ?
O4U C2U N3U 119.9(5) . . ?
C2U N3U H3UA 120.0 . . ?
C2U N3U H3UB 120.0 . . ?
H3UA N3U H3UB 120.0 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C2S C1S H1SA 109.5 . . ?
C2S C1S H1SB 109.5 . . ?
C2S C1S H1SC 109.5 . . ?
N3S C2S C1S 178.9(7) . . ?

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 O2 C3 C3M 172.2(4) . . . . ?
O1 O2 C3 C4 48.5(6) . . . . ?
O1 O2 C3 O13 -73.3(5) . . . . ?
O2 O1 C12A C5A -105.8(4) . . . . ?
O2 O1 C12A C8A 135.5(4) . . . . ?
O2 O1 C12A C12 15.5(6) . . . . ?
O2 C3 C4 C5 -94.6(6) . . . . ?
O2 C3 O13 C12 35.0(6) . . . . ?
C3 C4 C5 C5A 57.9(7) . . . . ?
C3M C3 C4 C5 146.7(5) . . . . ?
C3M C3 O13 C12 147.6(5) . . . . ?
C4 C3 O13 C12 -88.4(5) . . . . ?
C4 C5 C5A C6 -167.0(5) . . . . ?
C4 C5 C5A C12A -39.6(7) . . . . ?
C5 C5A C6 C6M -55.3(6) . . . . ?
C5 C5A C6 C7 -179.3(4) . . . . ?
C5 C5A C12A O1 71.6(6) . . . . ?
C5 C5A C12A C8A -175.4(5) . . . . ?
C5 C5A C12A C12 -48.2(6) . . . . ?
C5A C6 C7 C8 -57.7(6) . . . . ?
C6 C5A C12A O1 -162.0(4) . . . . ?
C6 C5A C12A C8A -49.0(6) . . . . ?
C6 C5A C12A C12 78.2(6) . . . . ?
C6 C7 C8 C8A 57.2(6) . . . . ?
C6M C6 C7 C8 177.6(5) . . . . ?
C7 C8 C8A C9 -178.8(4) . . . . ?
C7 C8 C8A C12A -52.1(6) . . . . ?
C8 C8A C9 C9M -51.7(6) . . . . ?
C8 C8A C9 C10 73.9(6) . . . . ?
C8 C8A C12A O1 162.0(4) . . . . ?
C8 C8A C12A C5A 47.9(6) . . . . ?
C8 C8A C12A C12 -79.4(6) . . . . ?
C8A C9 C10 O11 62.6(5) . . . . ?
C8A C9 C10 O14 179.5(4) . . . . ?
C9 C8A C12A O1 -70.4(5) . . . . ?
C9 C8A C12A C5A 175.6(4) . . . . ?
C9 C8A C12A C12 48.3(6) . . . . ?
C9 C10 O11 C12 -65.4(5) . . . . ?
C9 C10 O14 C15 164.7(4) . . . . ?
C9M C9 C10 O11 -171.4(4) . . . . ?
C9M C9 C10 O14 -54.4(6) . . . . ?
C10 O11 C12 C12A 57.1(5) . . . . ?
C10 O11 C12 O13 -177.3(4) . . . . ?
C10 O14 C15 O16 6.5(8) . . . . ?
C10 O14 C15 C17 -170.2(4) . . . . ?
O11 C10 O14 C15 -75.9(5) . . . . ?
O11 C12 C12A O1 66.7(6) . . . . ?
O11 C12 C12A C5A -176.0(4) . . . . ?
O11 C12 C12A C8A -48.5(6) . . . . ?
O11 C12 O13 C3 -97.3(5) . . . . ?
C12A O1 O2 C3 44.0(5) . . . . ?
C12A C5A C6 C6M 177.5(4) . . . . ?
C12A C5A C6 C7 53.5(6) . . . . ?
C12A C8A C9 C9M -179.7(5) . . . . ?
C12A C8A C9 C10 -54.0(6) . . . . ?
C12A C12 O13 C3 26.5(6) . . . . ?
O13 C3 C4 C5 26.4(7) . . . . ?
O13 C12 C12A O1 -53.3(6) . . . . ?
O13 C12 C12A C5A 64.1(6) . . . . ?
O13 C12 C12A C8A -168.4(4) . . . . ?
O14 C10 O11 C12 176.1(4) . . . . ?
O14 C15 C17 C18 -171.1(5) . . . . ?
C15 C17 C18 C19 -173.5(5) . . . . ?
O16 C15 C17 C18 12.3(8) . . . . ?
C17 C18 C19 O20 10.5(9) . . . . ?
C17 C18 C19 O21 -170.9(6) . . . . ?

_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 1.657
_oxdiff_exptl_absorpt_empirical_full_min 0.567
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.448(3) 5152 7450 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.552(3) 4528 7450 nmt 1.0016 -0.0180 0.0087 0.0058 0.9997 -0.0199 -0.0187
0.0938 0.9976

_twin_special_details            
; 
Component 2 rotated by 2.6510° 
around [0.94 0.20 0.26] (reciprocal) or [0.91 0.37 0.20] (direct) 
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shape_based
_database_code_depnum_ccdc_archive 'CCDC 2427254'
loop_
_audit_author_name
_audit_author_address
'Laszlo Fabian'
;University of East Anglia
United Kingdom
;
_audit_update_record             
;
2025-10-07 deposited with the CCDC.	2025-10-15 downloaded from the CCDC.
;
_audit_creation_date             2025-09-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424ae for OlexSys, GUI svn.r7311)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H28 O8), C6 H12 N2'
_chemical_formula_sum            'C44 H68 N2 O16'
_chemical_formula_weight         881.00
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C44 H66 N2 O16'
_chemical_oxdiff_usercomment     arts-ure-etoh
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           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                   10.3355(2)
_cell_length_b                   10.1548(2)
_cell_length_c                   21.6741(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.644(2)
_cell_angle_gamma                90
_cell_volume                     2219.64(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    19686
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.9990
_cell_measurement_theta_min      4.1750
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.813
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             948
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0376
0 1 0 0.1176
0 -1 0 0.1436
0 0 -1 0.0121
0 0 1 0.0030
1 0 0 0.0196

_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9995 -0.0002 -0.0001 0.0038 0.1181 0.0966
-0.0002 0.9994 -0.0003 -0.1410 0.0381 -0.0409
0.0002 -0.9994 0.0003 0.1410 -0.0381 0.0409
-0.0002 -0.0001 -0.9995 -0.0257 -0.0289 0.0617
0.0002 0.0001 0.9995 0.0257 0.0289 -0.0617
0.9995 0.0002 0.0001 -0.0038 -0.1181 -0.0966

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            31749
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.338
_diffrn_reflns_theta_min         4.181
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00   3.00   0.50    1.31    --  -47.29 104.00-144.00  168
  2  ω     18.00  58.00   0.50    1.31    --   47.29-104.00 113.00   80
  3  ω   -155.00 -89.00   0.50    5.23    --  -91.75-104.00 113.00  132
  4  ω    -73.00 -47.00   0.50    5.23    --  -91.75 104.00-144.00   52
  5  ω    109.00 175.00   0.50    5.23    --  106.64 104.00-144.00  132
  6  ω     77.00 105.00   0.50    5.23    --  106.64-104.00 113.00   56
  7  ω    -38.00  24.00   0.50    1.31    --  -47.29  37.00 120.00  124
  8  ω    -24.00  27.00   0.50    1.31    --  -47.29  19.00-150.00  102
  9  ω    -26.00  10.00   0.50    1.31    --  -47.29  19.00-180.00   72
 10  ω    -53.00 -13.00   0.50    1.31    --  -47.29 125.00   0.00   80
 11  ω     -7.00  27.00   0.50    1.31    --  -47.29  19.00  30.00   68
 12  ω     31.00  62.00   0.50    1.31    --   47.29 -57.00-150.00   62
 13  ω    -27.00  18.00   0.50    1.31    --   47.29 -19.00-120.00   90
 14  ω    -16.00  26.00   0.50    1.31    --   47.29 -19.00-180.00   84
 15  ω    -24.00   2.00   0.50    1.31    --   47.29 -19.00  90.00   52
 16  ω    -49.00 -21.00   0.50    5.23    --  -91.75  45.00-120.00   56
 17  ω    -71.00 -22.00   0.50    5.23    --  -91.75  61.00-180.00   98
 18  ω   -163.00-103.00   0.50    5.23    --  -91.75 -94.00-180.00  120
 19  ω   -163.00-132.00   0.50    5.23    --  -91.75 -61.00 -30.00   62
 20  ω    -51.00 -20.00   0.50    5.23    --  -91.75  45.00 -60.00   62
 21  ω    -51.00 -25.00   0.50    5.23    --  -91.75  45.00 150.00   52
 22  ω   -163.00-106.00   0.50    5.23    --  -91.75 -94.00  60.00  114
 23  ω    -57.00 -26.00   0.50    5.23    --  -91.75 125.00   0.00   62
 24  ω   -159.00-131.00   0.50    5.23    --  -91.75 -61.00 150.00   56
 25  ω    -51.00 -26.00   0.50    5.23    --  -91.75  45.00 -30.00   50
 26  ω    -51.00 -22.00   0.50    5.23    --  -91.75  45.00  60.00   58
 27  ω   -153.00-106.00   0.50    5.23    --  -91.75 -77.00  60.00   94
 28  ω   -149.00-123.00   0.50    5.23    --  -91.75 -77.00 -60.00   52
 29  ω   -128.00 -99.00   0.50    5.23    --  -91.75 -61.00 -30.00   58
 30  ω   -163.00 -99.00   0.50    5.23    --  -91.75 -61.00   0.00  128
 31  ω    -47.00 -20.00   0.50    5.23    --  -91.75  45.00  30.00   54
 32  ω     47.00 110.00   0.50    5.23    --  106.64-125.00 -90.00  126
 33  ω     42.00  67.00   0.50    5.23    --  106.64 -61.00-120.00   50
 34  ω     48.00  74.00   0.50    5.23    --  106.64 -94.00 -60.00   52
 35  ω     41.00  99.00   0.50    5.23    --  106.64-125.00  30.00  116
 36  ω     79.00 104.00   0.50    5.23    --  106.64 -94.00 150.00   50
 37  ω     35.00  61.00   0.50    5.23    --  106.64 -94.00 150.00   52
 38  ω     37.00  62.00   0.50    5.23    --  106.64 -61.00 -60.00   50
 39  ω     65.00 111.00   0.50    5.23    --  106.64-125.00  60.00   92
 40  ω     57.00 111.00   0.50    5.23    --  106.64-125.00  90.00  108
 41  ω    136.00 162.00   0.50    5.23    --  106.64 125.00 -60.00   52
 42  ω    106.00 132.00   0.50    5.23    --  106.64 125.00 -60.00   52
 43  ω     82.00 108.00   0.50    5.23    --  106.64-107.00 161.75   52
 44  ω     78.00 104.00   0.50    5.23    --  106.64 -94.00-120.00   52
 45  ω     54.00  79.00   0.50    5.23    --  106.64-107.00 161.75   50
 46  ω     52.00 102.00   0.50    5.23    --  106.64 -94.00 -90.00  100
 47  ω     49.00  74.00   0.50    5.23    --  106.64 -94.00-120.00   50
 48  ω     35.00  60.00   0.50    5.23    --  106.64 -61.00 150.00   50
 49  ω    138.00 178.00   0.50    5.23    --  106.64  61.00 -90.00   80
 50  ω     99.00 124.00   0.50    5.23    --  106.64  61.00 -90.00   50
 51  ω     39.00 108.00   0.50    5.23    --  106.64-125.00 120.00  138
 52  ω     79.00 105.00   0.50    5.23    --  106.64 -94.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0038105000
_diffrn_orient_matrix_UB_12      -0.1410753000
_diffrn_orient_matrix_UB_13      0.0257442000
_diffrn_orient_matrix_UB_21      -0.1181596000
_diffrn_orient_matrix_UB_22      0.0380903000
_diffrn_orient_matrix_UB_23      0.0289788000
_diffrn_orient_matrix_UB_31      -0.0966374000
_diffrn_orient_matrix_UB_32      -0.0409984000
_diffrn_orient_matrix_UB_33      -0.0616861000
_diffrn_oxdiff_ac3_digest_hkl    0199a88f0e7c2154d2d000fcd7f4aff194e232
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.908
_reflns_number_gt                8181
_reflns_number_total             8877
_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 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 3451 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(7)
_refine_ls_extinction_coef       0.0025(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   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         8877
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.060
_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)+(0.0512P)²+0.2862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0980
_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:
 C5A(H5C), C6(H6), C8A(H8C), C9(H9), C10(H10), C12(H12), C5AB(H5BX), C6B(H6B),
 C8AB(H8AB), C9B(H9B), C10B(H10B), C12B(H12B)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C17(H17A,H17B), C18(H18A,
 H18B), C3D(H3DA,H3DB), C4D(H4DA,H4DB), C5D(H5DA,H5DB), C6D(H6DA,H6DB),
 C7D(H7DA,H7DB), C8D(H8DA,H8DB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C7B(H7BA,H7BB),
  C8B(H8BA,H8BB), C17B(H17C,H17D), C18B(H18C,H18D)
2.c Idealised Me refined as rotating group:
 C3M(H3MA,H3MB,H3MC), C6M(H6MA,H6MB,H6MC), C9M(H9MA,H9MB,H9MC), C3MB(H3MD,H3ME,
 H3MF), C6MB(H6MD,H6ME,H6MF), C9MB(H9MD,H9ME,H9MF)
2.d Idealised tetrahedral OH refined as rotating group:
 O21(H21), O21B(H21B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.12394(17) 0.70148(19) 0.23690(8) 0.0272(4) Uani 1 1 d . . . . .
O2 O 1.18412(18) 0.7026(2) 0.18114(9) 0.0315(4) Uani 1 1 d . . . . .
C3 C 1.2409(3) 0.8270(3) 0.17663(14) 0.0323(6) Uani 1 1 d . . . . .
C4 C 1.3280(3) 0.8717(3) 0.23970(14) 0.0335(6) Uani 1 1 d . . . . .
H4A H 1.361794 0.792727 0.264902 0.040 Uiso 1 1 calc R U . . .
H4B H 1.405366 0.919951 0.231109 0.040 Uiso 1 1 calc R U . . .
C5 C 1.2573(3) 0.9599(3) 0.27916(14) 0.0315(6) Uani 1 1 d . . . . .
H5A H 1.236009 1.044487 0.256526 0.038 Uiso 1 1 calc R U . . .
H5B H 1.319926 0.979227 0.319672 0.038 Uiso 1 1 calc R U . . .
C5A C 1.1287(3) 0.9045(3) 0.29411(12) 0.0262(5) Uani 1 1 d . . . . .
H5C H 1.157368 0.842848 0.330502 0.031 Uiso 1 1 calc R U . . .
C6 C 1.0487(3) 1.0134(3) 0.31791(13) 0.0275(5) Uani 1 1 d . . . . .
H6 H 1.022431 1.080006 0.283455 0.033 Uiso 1 1 calc R U . . .
C7 C 0.9227(3) 0.9560(3) 0.33306(13) 0.0305(6) Uani 1 1 d . . . . .
H7A H 0.947264 0.895205 0.369448 0.037 Uiso 1 1 calc R U . . .
H7B H 0.869406 1.028298 0.345524 0.037 Uiso 1 1 calc R U . . .
C8 C 0.8384(3) 0.8820(3) 0.27731(13) 0.0273(6) Uani 1 1 d . . . . .
H8A H 0.807969 0.944025 0.241866 0.033 Uiso 1 1 calc R U . . .
H8B H 0.759058 0.845585 0.289818 0.033 Uiso 1 1 calc R U . . .
C8A C 0.9164(3) 0.7696(3) 0.25525(12) 0.0241(5) Uani 1 1 d . . . . .
H8C H 0.941951 0.707306 0.291602 0.029 Uiso 1 1 calc R U . . .
C9 C 0.8374(3) 0.6895(3) 0.19902(12) 0.0264(5) Uani 1 1 d . . . . .
H9 H 0.893048 0.612108 0.192876 0.032 Uiso 1 1 calc R U . . .
C10 C 0.8176(3) 0.7730(3) 0.13949(12) 0.0274(6) Uani 1 1 d . . . . .
H10 H 0.759521 0.850673 0.141890 0.033 Uiso 1 1 calc R U . . .
O11 O 0.94090(17) 0.8118(2) 0.12683(8) 0.0290(4) Uani 1 1 d . . . . .
C12 C 1.0187(3) 0.8902(3) 0.17568(12) 0.0269(5) Uani 1 1 d . . . . .
H12 H 0.969373 0.973577 0.179327 0.032 Uiso 1 1 calc R U . . .
C12A C 1.0464(3) 0.8205(3) 0.23967(12) 0.0242(5) Uani 1 1 d . . . . .
O13 O 1.13494(18) 0.9216(2) 0.15554(9) 0.0311(4) Uani 1 1 d . . . . .
O14 O 0.76358(17) 0.6911(2) 0.08600(8) 0.0303(4) Uani 1 1 d . . . . .
C15 C 0.6359(3) 0.7108(3) 0.05611(12) 0.0305(6) Uani 1 1 d . . . . .
O16 O 0.56677(19) 0.7959(3) 0.07058(10) 0.0400(5) Uani 1 1 d . . . . .
C17 C 0.5953(3) 0.6155(4) 0.00244(13) 0.0398(8) Uani 1 1 d . . . . .
H17A H 0.633874 0.527969 0.015636 0.048 Uiso 1 1 calc R U . . .
H17B H 0.631457 0.645383 -0.033875 0.048 Uiso 1 1 calc R U . . .
C18 C 0.4460(3) 0.6028(4) -0.01821(13) 0.0350(7) Uani 1 1 d . . . . .
H18A H 0.406604 0.691967 -0.023863 0.042 Uiso 1 1 calc R U . . .
H18B H 0.424105 0.557675 -0.059690 0.042 Uiso 1 1 calc R U . . .
C19 C 0.3845(3) 0.5276(3) 0.02803(13) 0.0331(6) Uani 1 1 d . . . . .
O20 O 0.4469(2) 0.4653(3) 0.07239(10) 0.0474(6) Uani 1 1 d . . . . .
O21 O 0.2553(2) 0.5362(3) 0.01352(11) 0.0464(6) Uani 1 1 d . . . . .
H21 H 0.223824 0.499326 0.041704 0.070 Uiso 1 1 calc R U . . .
C3M C 1.3149(3) 0.8136(4) 0.12392(15) 0.0441(8) Uani 1 1 d . . . . .
H3MA H 1.345500 0.900455 0.113580 0.066 Uiso 1 1 calc R U . . .
H3MB H 1.255613 0.776230 0.086448 0.066 Uiso 1 1 calc R U . . .
H3MC H 1.391335 0.755267 0.137592 0.066 Uiso 1 1 calc R U . . .
C6M C 1.1302(3) 1.0833(3) 0.37633(14) 0.0356(6) Uani 1 1 d . . . . .
H6MA H 1.075820 1.151335 0.390340 0.053 Uiso 1 1 calc R U . . .
H6MB H 1.208386 1.124159 0.365643 0.053 Uiso 1 1 calc R U . . .
H6MC H 1.158586 1.019086 0.410358 0.053 Uiso 1 1 calc R U . . .
C9M C 0.7063(3) 0.6364(3) 0.21033(13) 0.0324(6) Uani 1 1 d . . . . .
H9MA H 0.664652 0.579885 0.174860 0.049 Uiso 1 1 calc R U . . .
H9MB H 0.647059 0.710096 0.213804 0.049 Uiso 1 1 calc R U . . .
H9MC H 0.722933 0.585100 0.249577 0.049 Uiso 1 1 calc R U . . .
N1D N 0.1118(2) 0.4025(3) 0.07504(11) 0.0297(5) Uani 1 1 d . . . . .
N2D N -0.0483(2) 0.2644(2) 0.12238(10) 0.0246(5) Uani 1 1 d . . . . .
C3D C 0.1676(3) 0.3769(4) 0.14232(15) 0.0424(8) Uani 1 1 d . . . . .
H3DA H 0.192759 0.461271 0.164616 0.051 Uiso 1 1 calc R U . . .
H3DB H 0.248502 0.322319 0.146766 0.051 Uiso 1 1 calc R U . . .
C4D C 0.0659(3) 0.3052(4) 0.17222(13) 0.0385(7) Uani 1 1 d . . . . .
H4DA H 0.107422 0.226842 0.195654 0.046 Uiso 1 1 calc R U . . .
H4DB H 0.035551 0.364377 0.202501 0.046 Uiso 1 1 calc R U . . .
C5D C 0.0852(3) 0.2745(3) 0.04144(15) 0.0405(7) Uani 1 1 d . . . . .
H5DA H 0.170194 0.229723 0.041191 0.049 Uiso 1 1 calc R U . . .
H5DB H 0.038580 0.290010 -0.002959 0.049 Uiso 1 1 calc R U . . .
C6D C 0.0002(3) 0.1871(3) 0.07421(14) 0.0337(6) Uani 1 1 d . . . . .
H6DA H -0.076044 0.152255 0.042566 0.040 Uiso 1 1 calc R U . . .
H6DB H 0.053438 0.111577 0.094587 0.040 Uiso 1 1 calc R U . . .
C7D C -0.0148(3) 0.4723(3) 0.06886(15) 0.0351(7) Uani 1 1 d . . . . .
H7DA H -0.049417 0.497321 0.024138 0.042 Uiso 1 1 calc R U . . .
H7DB H -0.001059 0.553822 0.094511 0.042 Uiso 1 1 calc R U . . .
C8D C -0.1162(3) 0.3830(3) 0.09148(14) 0.0309(6) Uani 1 1 d . . . . .
H8DA H -0.157609 0.431721 0.121725 0.037 Uiso 1 1 calc R U . . .
H8DB H -0.187089 0.356821 0.054943 0.037 Uiso 1 1 calc R U . . .
O1B O -0.44290(17) 0.30390(18) 0.56465(8) 0.0239(4) Uani 1 1 d . . . . .
O2B O -0.58754(17) 0.31393(18) 0.54174(8) 0.0247(4) Uani 1 1 d . . . . .
C3B C -0.6477(3) 0.1993(3) 0.55948(11) 0.0248(5) Uani 1 1 d . . . . .
C4B C -0.5959(3) 0.1661(3) 0.62966(12) 0.0292(6) Uani 1 1 d . . . . .
H4BA H -0.565495 0.248287 0.652888 0.035 Uiso 1 1 calc R U . . .
H4BB H -0.669918 0.130340 0.646804 0.035 Uiso 1 1 calc R U . . .
C5B C -0.4825(3) 0.0672(3) 0.64194(12) 0.0282(6) Uani 1 1 d . . . . .
H5BA H -0.517151 -0.018331 0.623422 0.034 Uiso 1 1 calc R U . . .
H5BB H -0.453869 0.054428 0.688215 0.034 Uiso 1 1 calc R U . . .
C5AB C -0.3598(3) 0.1024(3) 0.61618(11) 0.0256(5) Uani 1 1 d . . . . .
H5BX H -0.306721 0.165732 0.647003 0.031 Uiso 1 1 calc R U . . .
C6B C -0.2712(3) -0.0197(3) 0.61550(12) 0.0267(5) Uani 1 1 d . . . . .
H6B H -0.322164 -0.085717 0.585508 0.032 Uiso 1 1 calc R U . . .
C7B C -0.1473(3) 0.0188(3) 0.59211(13) 0.0313(6) Uani 1 1 d . . . . .
H7BA H -0.094021 0.081581 0.622285 0.038 Uiso 1 1 calc R U . . .
H7BB H -0.092527 -0.060645 0.590529 0.038 Uiso 1 1 calc R U . . .
C8B C -0.1825(3) 0.0814(3) 0.52684(12) 0.0278(6) Uani 1 1 d . . . . .
H8BA H -0.229666 0.015999 0.496087 0.033 Uiso 1 1 calc R U . . .
H8BB H -0.099925 0.106384 0.513726 0.033 Uiso 1 1 calc R U . . .
C8AB C -0.2696(2) 0.2030(3) 0.52547(11) 0.0231(5) Uani 1 1 d . . . . .
H8AB H -0.215921 0.270023 0.553878 0.028 Uiso 1 1 calc R U . . .
C9B C -0.3110(3) 0.2659(3) 0.45943(11) 0.0243(5) Uani 1 1 d . . . . .
H9B H -0.357908 0.350197 0.464143 0.029 Uiso 1 1 calc R U . . .
C10B C -0.4100(3) 0.1750(3) 0.41793(11) 0.0246(5) Uani 1 1 d . . . . .
H10B H -0.370061 0.086330 0.414350 0.029 Uiso 1 1 calc R U . . .
O11B O -0.52599(17) 0.16431(18) 0.44218(8) 0.0243(4) Uani 1 1 d . . . . .
C12B C -0.5000(3) 0.1007(3) 0.50282(11) 0.0220(5) Uani 1 1 d . . . . .
H12B H -0.467253 0.009458 0.497874 0.026 Uiso 1 1 calc R U . . .
C12C C -0.3943(3) 0.1744(2) 0.55195(11) 0.0222(5) Uani 1 1 d . . . . .
O13B O -0.62255(17) 0.09212(18) 0.52055(8) 0.0236(4) Uani 1 1 d . . . . .
O14B O -0.4547(2) 0.23333(19) 0.35707(8) 0.0294(4) Uani 1 1 d . . . . .
C15B C -0.4394(2) 0.1648(3) 0.30572(12) 0.0255(5) Uani 1 1 d . . . . .
O16B O -0.3936(2) 0.0554(2) 0.30809(9) 0.0364(5) Uani 1 1 d . . . . .
C17B C -0.4893(3) 0.2422(3) 0.24648(12) 0.0327(6) Uani 1 1 d . . . . .
H17C H -0.461732 0.335244 0.253980 0.039 Uiso 1 1 calc R U . . .
H17D H -0.587438 0.239644 0.235956 0.039 Uiso 1 1 calc R U . . .
C18B C -0.4376(3) 0.1895(3) 0.19060(12) 0.0329(6) Uani 1 1 d . . . . .
H18C H -0.453117 0.093301 0.187270 0.039 Uiso 1 1 calc R U . . .
H18D H -0.488405 0.230484 0.151246 0.039 Uiso 1 1 calc R U . . .
C19B C -0.2911(3) 0.2163(3) 0.19621(11) 0.0281(6) Uani 1 1 d . . . . .
O20B O -0.2286(2) 0.2951(2) 0.23274(10) 0.0407(5) Uani 1 1 d . . . . .
O21B O -0.24154(19) 0.1461(2) 0.15577(8) 0.0287(4) Uani 1 1 d . . . . .
H21B H -0.172883 0.182942 0.149408 0.043 Uiso 1 1 calc R U . . .
C3MB C -0.7945(3) 0.2270(3) 0.54189(14) 0.0326(6) Uani 1 1 d . . . . .
H3MD H -0.818432 0.258840 0.498187 0.049 Uiso 1 1 calc R U . . .
H3ME H -0.816780 0.294253 0.570303 0.049 Uiso 1 1 calc R U . . .
H3MF H -0.843626 0.146024 0.545761 0.049 Uiso 1 1 calc R U . . .
C6MB C -0.2309(3) -0.0833(3) 0.68073(13) 0.0355(7) Uani 1 1 d . . . . .
H6MD H -0.192732 -0.016280 0.711984 0.053 Uiso 1 1 calc R U . . .
H6ME H -0.164994 -0.152198 0.679808 0.053 Uiso 1 1 calc R U . . .
H6MF H -0.309135 -0.122158 0.692249 0.053 Uiso 1 1 calc R U . . .
C9MB C -0.1929(3) 0.2991(3) 0.43027(14) 0.0351(6) Uani 1 1 d . . . . .
H9MD H -0.151600 0.217437 0.420053 0.053 Uiso 1 1 calc R U . . .
H9ME H -0.127927 0.350539 0.460492 0.053 Uiso 1 1 calc R U . . .
H9MF H -0.223556 0.350586 0.391587 0.053 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
O1 O2 1.475(2) . ?
O1 C12A 1.459(3) . ?
O2 C3 1.405(4) . ?
C3 C4 1.532(4) . ?
C3 O13 1.454(3) . ?
C3 C3M 1.513(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.530(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C5A 1.541(4) . ?
C5A H5C 1.0000 . ?
C5A C6 1.536(4) . ?
C5A C12A 1.551(4) . ?
C6 H6 1.0000 . ?
C6 C7 1.527(4) . ?
C6 C6M 1.533(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.524(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C8A 1.533(4) . ?
C8A H8C 1.0000 . ?
C8A C9 1.542(4) . ?
C8A C12A 1.544(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.519(4) . ?
C9 C9M 1.528(4) . ?
C10 H10 1.0000 . ?
C10 O11 1.416(3) . ?
C10 O14 1.437(3) . ?
O11 C12 1.424(3) . ?
C12 H12 1.0000 . ?
C12 C12A 1.527(4) . ?
C12 O13 1.402(3) . ?
O14 C15 1.352(3) . ?
C15 O16 1.206(4) . ?
C15 C17 1.501(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.515(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.507(4) . ?
C19 O20 1.212(4) . ?
C19 O21 1.306(3) . ?
O21 H21 0.8400 . ?
C3M H3MA 0.9800 . ?
C3M H3MB 0.9800 . ?
C3M H3MC 0.9800 . ?
C6M H6MA 0.9800 . ?
C6M H6MB 0.9800 . ?
C6M H6MC 0.9800 . ?
C9M H9MA 0.9800 . ?
C9M H9MB 0.9800 . ?
C9M H9MC 0.9800 . ?
N1D C3D 1.469(4) . ?
N1D C5D 1.485(4) . ?
N1D C7D 1.468(4) . ?
N2D C4D 1.474(4) . ?
N2D C6D 1.479(3) . ?
N2D C8D 1.479(4) . ?
C3D H3DA 0.9900 . ?
C3D H3DB 0.9900 . ?
C3D C4D 1.534(4) . ?
C4D H4DA 0.9900 . ?
C4D H4DB 0.9900 . ?
C5D H5DA 0.9900 . ?
C5D H5DB 0.9900 . ?
C5D C6D 1.529(4) . ?
C6D H6DA 0.9900 . ?
C6D H6DB 0.9900 . ?
C7D H7DA 0.9900 . ?
C7D H7DB 0.9900 . ?
C7D C8D 1.545(4) . ?
C8D H8DA 0.9900 . ?
C8D H8DB 0.9900 . ?
O1B O2B 1.472(2) . ?
O1B C12C 1.455(3) . ?
O2B C3B 1.412(3) . ?
C3B C4B 1.536(3) . ?
C3B O13B 1.435(3) . ?
C3B C3MB 1.507(4) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.522(4) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C5B C5AB 1.536(4) . ?
C5AB H5BX 1.0000 . ?
C5AB C6B 1.543(4) . ?
C5AB C12C 1.543(3) . ?
C6B H6B 1.0000 . ?
C6B C7B 1.528(4) . ?
C6B C6MB 1.527(4) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C7B C8B 1.521(4) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C8B C8AB 1.525(4) . ?
C8AB H8AB 1.0000 . ?
C8AB C9B 1.540(3) . ?
C8AB C12C 1.549(3) . ?
C9B H9B 1.0000 . ?
C9B C10B 1.518(4) . ?
C9B C9MB 1.530(4) . ?
C10B H10B 1.0000 . ?
C10B O11B 1.415(3) . ?
C10B O14B 1.428(3) . ?
O11B C12B 1.436(3) . ?
C12B H12B 1.0000 . ?
C12B C12C 1.542(3) . ?
C12B O13B 1.404(3) . ?
O14B C15B 1.351(3) . ?
C15B O16B 1.205(4) . ?
C15B C17B 1.497(4) . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C17B C18B 1.524(4) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C18B C19B 1.517(4) . ?
C19B O20B 1.209(4) . ?
C19B O21B 1.317(3) . ?
O21B H21B 0.8400 . ?
C3MB H3MD 0.9800 . ?
C3MB H3ME 0.9800 . ?
C3MB H3MF 0.9800 . ?
C6MB H6MD 0.9800 . ?
C6MB H6ME 0.9800 . ?
C6MB H6MF 0.9800 . ?
C9MB H9MD 0.9800 . ?
C9MB H9ME 0.9800 . ?
C9MB H9MF 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12A O1 O2 111.18(18) . . ?
C3 O2 O1 108.74(19) . . ?
O2 C3 C4 112.2(2) . . ?
O2 C3 O13 108.6(2) . . ?
O2 C3 C3M 105.0(3) . . ?
O13 C3 C4 109.9(2) . . ?
O13 C3 C3M 107.0(2) . . ?
C3M C3 C4 113.9(2) . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.4(2) . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C4 C5 H5A 108.2 . . ?
C4 C5 H5B 108.2 . . ?
C4 C5 C5A 116.3(3) . . ?
H5A C5 H5B 107.4 . . ?
C5A C5 H5A 108.2 . . ?
C5A C5 H5B 108.2 . . ?
C5 C5A H5C 105.9 . . ?
C5 C5A C12A 113.3(2) . . ?
C6 C5A C5 111.1(2) . . ?
C6 C5A H5C 105.9 . . ?
C6 C5A C12A 113.9(2) . . ?
C12A C5A H5C 105.9 . . ?
C5A C6 H6 108.3 . . ?
C7 C6 C5A 110.2(2) . . ?
C7 C6 H6 108.3 . . ?
C7 C6 C6M 109.9(2) . . ?
C6M C6 C5A 111.8(2) . . ?
C6M C6 H6 108.3 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 112.6(2) . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C7 C8 C8A 111.5(2) . . ?
H8A C8 H8B 108.0 . . ?
C8A C8 H8A 109.3 . . ?
C8A C8 H8B 109.3 . . ?
C8 C8A H8C 107.0 . . ?
C8 C8A C9 114.6(2) . . ?
C8 C8A C12A 111.2(2) . . ?
C9 C8A H8C 107.0 . . ?
C9 C8A C12A 109.8(2) . . ?
C12A C8A H8C 107.0 . . ?
C8A C9 H9 107.4 . . ?
C10 C9 C8A 109.1(2) . . ?
C10 C9 H9 107.4 . . ?
C10 C9 C9M 112.0(2) . . ?
C9M C9 C8A 113.2(2) . . ?
C9M C9 H9 107.4 . . ?
C9 C10 H10 111.5 . . ?
O11 C10 C9 111.1(2) . . ?
O11 C10 H10 111.5 . . ?
O11 C10 O14 102.24(19) . . ?
O14 C10 C9 108.6(2) . . ?
O14 C10 H10 111.5 . . ?
C10 O11 C12 113.36(19) . . ?
O11 C12 H12 108.5 . . ?
O11 C12 C12A 112.3(2) . . ?
C12A C12 H12 108.5 . . ?
O13 C12 O11 106.2(2) . . ?
O13 C12 H12 108.5 . . ?
O13 C12 C12A 112.6(2) . . ?
O1 C12A C5A 105.8(2) . . ?
O1 C12A C8A 104.1(2) . . ?
O1 C12A C12 110.0(2) . . ?
C8A C12A C5A 112.1(2) . . ?
C12 C12A C5A 113.5(2) . . ?
C12 C12A C8A 110.8(2) . . ?
C12 O13 C3 112.9(2) . . ?
C15 O14 C10 117.9(2) . . ?
O14 C15 C17 110.7(3) . . ?
O16 C15 O14 123.6(3) . . ?
O16 C15 C17 125.7(3) . . ?
C15 C17 H17A 109.2 . . ?
C15 C17 H17B 109.2 . . ?
C15 C17 C18 112.2(3) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C17 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 C17 113.4(2) . . ?
C19 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
O20 C19 C18 124.3(3) . . ?
O20 C19 O21 124.3(3) . . ?
O21 C19 C18 111.4(2) . . ?
C19 O21 H21 109.5 . . ?
C3 C3M H3MA 109.5 . . ?
C3 C3M H3MB 109.5 . . ?
C3 C3M H3MC 109.5 . . ?
H3MA C3M H3MB 109.5 . . ?
H3MA C3M H3MC 109.5 . . ?
H3MB C3M H3MC 109.5 . . ?
C6 C6M H6MA 109.5 . . ?
C6 C6M H6MB 109.5 . . ?
C6 C6M H6MC 109.5 . . ?
H6MA C6M H6MB 109.5 . . ?
H6MA C6M H6MC 109.5 . . ?
H6MB C6M H6MC 109.5 . . ?
C9 C9M H9MA 109.5 . . ?
C9 C9M H9MB 109.5 . . ?
C9 C9M H9MC 109.5 . . ?
H9MA C9M H9MB 109.5 . . ?
H9MA C9M H9MC 109.5 . . ?
H9MB C9M H9MC 109.5 . . ?
C3D N1D C5D 108.8(3) . . ?
C7D N1D C3D 108.9(2) . . ?
C7D N1D C5D 108.2(2) . . ?
C4D N2D C6D 109.0(2) . . ?
C4D N2D C8D 109.1(2) . . ?
C6D N2D C8D 108.2(2) . . ?
N1D C3D H3DA 109.6 . . ?
N1D C3D H3DB 109.6 . . ?
N1D C3D C4D 110.3(2) . . ?
H3DA C3D H3DB 108.1 . . ?
C4D C3D H3DA 109.6 . . ?
C4D C3D H3DB 109.6 . . ?
N2D C4D C3D 109.7(2) . . ?
N2D C4D H4DA 109.7 . . ?
N2D C4D H4DB 109.7 . . ?
C3D C4D H4DA 109.7 . . ?
C3D C4D H4DB 109.7 . . ?
H4DA C4D H4DB 108.2 . . ?
N1D C5D H5DA 109.6 . . ?
N1D C5D H5DB 109.6 . . ?
N1D C5D C6D 110.1(2) . . ?
H5DA C5D H5DB 108.2 . . ?
C6D C5D H5DA 109.6 . . ?
C6D C5D H5DB 109.6 . . ?
N2D C6D C5D 109.8(2) . . ?
N2D C6D H6DA 109.7 . . ?
N2D C6D H6DB 109.7 . . ?
C5D C6D H6DA 109.7 . . ?
C5D C6D H6DB 109.7 . . ?
H6DA C6D H6DB 108.2 . . ?
N1D C7D H7DA 109.7 . . ?
N1D C7D H7DB 109.7 . . ?
N1D C7D C8D 109.9(2) . . ?
H7DA C7D H7DB 108.2 . . ?
C8D C7D H7DA 109.7 . . ?
C8D C7D H7DB 109.7 . . ?
N2D C8D C7D 109.5(2) . . ?
N2D C8D H8DA 109.8 . . ?
N2D C8D H8DB 109.8 . . ?
C7D C8D H8DA 109.8 . . ?
C7D C8D H8DB 109.8 . . ?
H8DA C8D H8DB 108.2 . . ?
C12C O1B O2B 111.45(17) . . ?
C3B O2B O1B 109.06(18) . . ?
O2B C3B C4B 111.8(2) . . ?
O2B C3B O13B 108.52(18) . . ?
O2B C3B C3MB 104.8(2) . . ?
O13B C3B C4B 110.3(2) . . ?
O13B C3B C3MB 107.2(2) . . ?
C3MB C3B C4B 113.9(2) . . ?
C3B C4B H4BA 108.7 . . ?
C3B C4B H4BB 108.7 . . ?
H4BA C4B H4BB 107.6 . . ?
C5B C4B C3B 114.0(2) . . ?
C5B C4B H4BA 108.7 . . ?
C5B C4B H4BB 108.7 . . ?
C4B C5B H5BA 108.1 . . ?
C4B C5B H5BB 108.1 . . ?
C4B C5B C5AB 116.6(2) . . ?
H5BA C5B H5BB 107.3 . . ?
C5AB C5B H5BA 108.1 . . ?
C5AB C5B H5BB 108.1 . . ?
C5B C5AB H5BX 106.4 . . ?
C5B C5AB C6B 110.8(2) . . ?
C5B C5AB C12C 113.1(2) . . ?
C6B C5AB H5BX 106.4 . . ?
C6B C5AB C12C 113.1(2) . . ?
C12C C5AB H5BX 106.4 . . ?
C5AB C6B H6B 108.4 . . ?
C7B C6B C5AB 109.9(2) . . ?
C7B C6B H6B 108.4 . . ?
C6MB C6B C5AB 111.9(2) . . ?
C6MB C6B H6B 108.4 . . ?
C6MB C6B C7B 109.7(2) . . ?
C6B C7B H7BA 109.3 . . ?
C6B C7B H7BB 109.3 . . ?
H7BA C7B H7BB 108.0 . . ?
C8B C7B C6B 111.6(2) . . ?
C8B C7B H7BA 109.3 . . ?
C8B C7B H7BB 109.3 . . ?
C7B C8B H8BA 109.2 . . ?
C7B C8B H8BB 109.2 . . ?
C7B C8B C8AB 112.1(2) . . ?
H8BA C8B H8BB 107.9 . . ?
C8AB C8B H8BA 109.2 . . ?
C8AB C8B H8BB 109.2 . . ?
C8B C8AB H8AB 107.1 . . ?
C8B C8AB C9B 113.4(2) . . ?
C8B C8AB C12C 112.1(2) . . ?
C9B C8AB H8AB 107.1 . . ?
C9B C8AB C12C 109.7(2) . . ?
C12C C8AB H8AB 107.1 . . ?
C8AB C9B H9B 107.6 . . ?
C10B C9B C8AB 108.2(2) . . ?
C10B C9B H9B 107.6 . . ?
C10B C9B C9MB 112.6(2) . . ?
C9MB C9B C8AB 113.0(2) . . ?
C9MB C9B H9B 107.6 . . ?
C9B C10B H10B 111.0 . . ?
O11B C10B C9B 110.02(19) . . ?
O11B C10B H10B 111.0 . . ?
O11B C10B O14B 104.22(19) . . ?
O14B C10B C9B 109.5(2) . . ?
O14B C10B H10B 111.0 . . ?
C10B O11B C12B 111.73(18) . . ?
O11B C12B H12B 108.6 . . ?
O11B C12B C12C 112.1(2) . . ?
C12C C12B H12B 108.6 . . ?
O13B C12B O11B 106.20(19) . . ?
O13B C12B H12B 108.6 . . ?
O13B C12B C12C 112.7(2) . . ?
O1B C12C C5AB 106.17(19) . . ?
O1B C12C C8AB 104.48(19) . . ?
O1B C12C C12B 110.4(2) . . ?
C5AB C12C C8AB 112.1(2) . . ?
C12B C12C C5AB 112.5(2) . . ?
C12B C12C C8AB 110.88(19) . . ?
C12B O13B C3B 113.85(19) . . ?
C15B O14B C10B 118.3(2) . . ?
O14B C15B C17B 110.8(2) . . ?
O16B C15B O14B 123.8(2) . . ?
O16B C15B C17B 125.4(2) . . ?
C15B C17B H17C 109.1 . . ?
C15B C17B H17D 109.1 . . ?
C15B C17B C18B 112.5(2) . . ?
H17C C17B H17D 107.8 . . ?
C18B C17B H17C 109.1 . . ?
C18B C17B H17D 109.1 . . ?
C17B C18B H18C 109.0 . . ?
C17B C18B H18D 109.0 . . ?
H18C C18B H18D 107.8 . . ?
C19B C18B C17B 113.0(2) . . ?
C19B C18B H18C 109.0 . . ?
C19B C18B H18D 109.0 . . ?
O20B C19B C18B 123.5(3) . . ?
O20B C19B O21B 124.4(3) . . ?
O21B C19B C18B 112.1(2) . . ?
C19B O21B H21B 109.5 . . ?
C3B C3MB H3MD 109.5 . . ?
C3B C3MB H3ME 109.5 . . ?
C3B C3MB H3MF 109.5 . . ?
H3MD C3MB H3ME 109.5 . . ?
H3MD C3MB H3MF 109.5 . . ?
H3ME C3MB H3MF 109.5 . . ?
C6B C6MB H6MD 109.5 . . ?
C6B C6MB H6ME 109.5 . . ?
C6B C6MB H6MF 109.5 . . ?
H6MD C6MB H6ME 109.5 . . ?
H6MD C6MB H6MF 109.5 . . ?
H6ME C6MB H6MF 109.5 . . ?
C9B C9MB H9MD 109.5 . . ?
C9B C9MB H9ME 109.5 . . ?
C9B C9MB H9MF 109.5 . . ?
H9MD C9MB H9ME 109.5 . . ?
H9MD C9MB H9MF 109.5 . . ?
H9ME C9MB H9MF 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
O1 O2 C3 C4 48.7(3) . . . . ?
O1 O2 C3 O13 -72.9(2) . . . . ?
O1 O2 C3 C3M 172.9(2) . . . . ?
O2 O1 C12A C5A -106.9(2) . . . . ?
O2 O1 C12A C8A 134.75(19) . . . . ?
O2 O1 C12A C12 16.0(3) . . . . ?
O2 C3 C4 C5 -95.0(3) . . . . ?
O2 C3 O13 C12 30.8(3) . . . . ?
C3 C4 C5 C5A 54.9(3) . . . . ?
C4 C3 O13 C12 -92.2(3) . . . . ?
C4 C5 C5A C6 -164.9(2) . . . . ?
C4 C5 C5A C12A -35.2(3) . . . . ?
C5 C5A C6 C7 -179.4(2) . . . . ?
C5 C5A C6 C6M -56.9(3) . . . . ?
C5 C5A C12A O1 68.7(3) . . . . ?
C5 C5A C12A C8A -178.4(2) . . . . ?
C5 C5A C12A C12 -52.0(3) . . . . ?
C5A C6 C7 C8 -55.0(3) . . . . ?
C6 C5A C12A O1 -163.0(2) . . . . ?
C6 C5A C12A C8A -50.1(3) . . . . ?
C6 C5A C12A C12 76.4(3) . . . . ?
C6 C7 C8 C8A 58.0(3) . . . . ?
C7 C8 C8A C9 179.8(2) . . . . ?
C7 C8 C8A C12A -55.0(3) . . . . ?
C8 C8A C9 C10 71.8(3) . . . . ?
C8 C8A C9 C9M -53.5(3) . . . . ?
C8 C8A C12A O1 164.83(19) . . . . ?
C8 C8A C12A C5A 50.9(3) . . . . ?
C8 C8A C12A C12 -77.0(3) . . . . ?
C8A C9 C10 O11 59.0(3) . . . . ?
C8A C9 C10 O14 170.7(2) . . . . ?
C9 C8A C12A O1 -67.3(2) . . . . ?
C9 C8A C12A C5A 178.8(2) . . . . ?
C9 C8A C12A C12 50.9(3) . . . . ?
C9 C10 O11 C12 -61.3(3) . . . . ?
C9 C10 O14 C15 109.2(3) . . . . ?
C10 O11 C12 C12A 57.4(3) . . . . ?
C10 O11 C12 O13 -179.1(2) . . . . ?
C10 O14 C15 O16 2.6(4) . . . . ?
C10 O14 C15 C17 -178.9(2) . . . . ?
O11 C10 O14 C15 -133.3(2) . . . . ?
O11 C12 C12A O1 62.8(3) . . . . ?
O11 C12 C12A C5A -178.9(2) . . . . ?
O11 C12 C12A C8A -51.8(3) . . . . ?
O11 C12 O13 C3 -91.2(3) . . . . ?
C12A O1 O2 C3 45.7(2) . . . . ?
C12A C5A C6 C7 51.2(3) . . . . ?
C12A C5A C6 C6M 173.6(2) . . . . ?
C12A C8A C9 C10 -54.1(3) . . . . ?
C12A C8A C9 C9M -179.5(2) . . . . ?
C12A C12 O13 C3 32.0(3) . . . . ?
O13 C3 C4 C5 25.9(3) . . . . ?
O13 C12 C12A O1 -57.0(3) . . . . ?
O13 C12 C12A C5A 61.3(3) . . . . ?
O13 C12 C12A C8A -171.6(2) . . . . ?
O14 C10 O11 C12 -177.0(2) . . . . ?
O14 C15 C17 C18 161.2(3) . . . . ?
C15 C17 C18 C19 -72.8(4) . . . . ?
O16 C15 C17 C18 -20.4(5) . . . . ?
C17 C18 C19 O20 -10.9(5) . . . . ?
C17 C18 C19 O21 170.2(3) . . . . ?
C3M C3 C4 C5 145.9(3) . . . . ?
C3M C3 O13 C12 143.7(3) . . . . ?
C6M C6 C7 C8 -178.6(2) . . . . ?
C9M C9 C10 O11 -174.9(2) . . . . ?
C9M C9 C10 O14 -63.2(3) . . . . ?
N1D C3D C4D N2D 9.3(4) . . . . ?
N1D C5D C6D N2D 9.5(4) . . . . ?
N1D C7D C8D N2D 9.6(3) . . . . ?
C3D N1D C5D C6D 53.1(3) . . . . ?
C3D N1D C7D C8D -64.5(3) . . . . ?
C4D N2D C6D C5D -64.5(3) . . . . ?
C4D N2D C8D C7D 53.3(3) . . . . ?
C5D N1D C3D C4D -64.0(3) . . . . ?
C5D N1D C7D C8D 53.6(3) . . . . ?
C6D N2D C4D C3D 53.8(3) . . . . ?
C6D N2D C8D C7D -65.2(3) . . . . ?
C7D N1D C3D C4D 53.8(4) . . . . ?
C7D N1D C5D C6D -65.1(3) . . . . ?
C8D N2D C4D C3D -64.2(3) . . . . ?
C8D N2D C6D C5D 54.0(3) . . . . ?
O1B O2B C3B C4B 48.7(2) . . . . ?
O1B O2B C3B O13B -73.2(2) . . . . ?
O1B O2B C3B C3MB 172.59(18) . . . . ?
O2B O1B C12C C5AB -106.4(2) . . . . ?
O2B O1B C12C C8AB 134.96(17) . . . . ?
O2B O1B C12C C12B 15.7(2) . . . . ?
O2B C3B C4B C5B -94.9(3) . . . . ?
O2B C3B O13B C12B 32.5(3) . . . . ?
C3B C4B C5B C5AB 56.0(3) . . . . ?
C4B C3B O13B C12B -90.3(2) . . . . ?
C4B C5B C5AB C6B -164.4(2) . . . . ?
C4B C5B C5AB C12C -36.3(3) . . . . ?
C5B C5AB C6B C7B -177.8(2) . . . . ?
C5B C5AB C6B C6MB -55.7(3) . . . . ?
C5B C5AB C12C O1B 69.2(3) . . . . ?
C5B C5AB C12C C8AB -177.3(2) . . . . ?
C5B C5AB C12C C12B -51.6(3) . . . . ?
C5AB C6B C7B C8B -57.2(3) . . . . ?
C6B C5AB C12C O1B -163.8(2) . . . . ?
C6B C5AB C12C C8AB -50.3(3) . . . . ?
C6B C5AB C12C C12B 75.4(3) . . . . ?
C6B C7B C8B C8AB 57.8(3) . . . . ?
C7B C8B C8AB C9B -178.0(2) . . . . ?
C7B C8B C8AB C12C -53.1(3) . . . . ?
C8B C8AB C9B C10B 70.8(3) . . . . ?
C8B C8AB C9B C9MB -54.6(3) . . . . ?
C8B C8AB C12C O1B 163.68(19) . . . . ?
C8B C8AB C12C C5AB 49.1(3) . . . . ?
C8B C8AB C12C C12B -77.4(3) . . . . ?
C8AB C9B C10B O11B 63.5(3) . . . . ?
C8AB C9B C10B O14B 177.5(2) . . . . ?
C9B C8AB C12C O1B -69.4(2) . . . . ?
C9B C8AB C12C C5AB 176.1(2) . . . . ?
C9B C8AB C12C C12B 49.5(3) . . . . ?
C9B C10B O11B C12B -65.5(3) . . . . ?
C9B C10B O14B C15B 123.5(2) . . . . ?
C10B O11B C12B C12C 58.5(3) . . . . ?
C10B O11B C12B O13B -178.01(19) . . . . ?
C10B O14B C15B O16B 2.3(4) . . . . ?
C10B O14B C15B C17B -178.9(2) . . . . ?
O11B C10B O14B C15B -118.9(2) . . . . ?
O11B C12B C12C O1B 65.0(3) . . . . ?
O11B C12B C12C C5AB -176.7(2) . . . . ?
O11B C12B C12C C8AB -50.3(3) . . . . ?
O11B C12B O13B C3B -94.1(2) . . . . ?
C12C O1B O2B C3B 45.0(2) . . . . ?
C12C C5AB C6B C7B 54.0(3) . . . . ?
C12C C5AB C6B C6MB 176.1(2) . . . . ?
C12C C8AB C9B C10B -55.4(3) . . . . ?
C12C C8AB C9B C9MB 179.2(2) . . . . ?
C12C C12B O13B C3B 29.0(3) . . . . ?
O13B C3B C4B C5B 26.0(3) . . . . ?
O13B C12B C12C O1B -54.8(3) . . . . ?
O13B C12B C12C C5AB 63.6(3) . . . . ?
O13B C12B C12C C8AB -170.0(2) . . . . ?
O14B C10B O11B C12B 177.14(19) . . . . ?
O14B C15B C17B C18B 162.7(2) . . . . ?
C15B C17B C18B C19B -71.2(3) . . . . ?
O16B C15B C17B C18B -18.5(4) . . . . ?
C17B C18B C19B O20B -15.7(4) . . . . ?
C17B C18B C19B O21B 165.8(3) . . . . ?
C3MB C3B C4B C5B 146.5(2) . . . . ?
C3MB C3B O13B C12B 145.2(2) . . . . ?
C6MB C6B C7B C8B 179.4(2) . . . . ?
C9MB C9B C10B O11B -170.9(2) . . . . ?
C9MB C9B C10B O14B -56.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.591
_oxdiff_exptl_absorpt_empirical_full_min 0.717
####################################################################### 
# 
# 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_ATS2-DABCO-2
_database_code_depnum_ccdc_archive 'CCDC 2427255'
loop_
_audit_author_name
_audit_author_address
'Laszlo Fabian'
;University of East Anglia
United Kingdom
;
_audit_update_record             
;
2025-02-26 deposited with the CCDC.	2025-10-15 downloaded from the CCDC.
;
_audit_creation_date             2023-09-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec141 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H28 O8, C19 H27 O8, C6 H13 N2'
_chemical_formula_sum            'C44 H68 N2 O16'
_chemical_formula_weight         881.00
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C44 H68 N2 O16'
_chemical_oxdiff_usercomment     'bis(artesunate) dabco salt cocrystal'
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           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                   11.0046(11)
_cell_length_b                   8.5912(8)
_cell_length_c                   23.6155(18)
_cell_angle_alpha                90
_cell_angle_beta                 98.743(9)
_cell_angle_gamma                90
_cell_volume                     2206.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6045
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      66.9450
_cell_measurement_theta_min      3.7230
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.885
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             948
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0128
0 0 1 0.0187
-2 -2 -1 0.0439
2 1 1 0.0529
2 -1 0 0.0750
3 0 1 0.0618
-1 1 0 0.0497

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0004 0.0000 -0.9993 0.0011 -0.0656 0.0061
0.0004 -0.0000 0.9993 -0.0011 0.0656 -0.0061
-2.0004 -1.9993 -1.0023 -0.3656 -0.0899 0.2786
2.0005 0.9995 1.0009 0.3163 0.1049 -0.1064
2.0003 -1.0001 -0.0011 0.2188 0.0693 0.2441
3.0007 -0.0005 0.9997 0.4011 0.1471 0.1018
-1.0002 1.0000 0.0013 -0.0848 -0.0422 -0.2082

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15522
_diffrn_reflns_point_group_measured_fraction_full 0.731
_diffrn_reflns_point_group_measured_fraction_max 0.731
_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         3.788
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_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  21.00   0.50   10.00    --  -49.31  22.00  65.00   96
  2  ω   -122.00 -44.00   0.50   10.00    --  -49.31 -22.00-100.00  156
  3  ω     50.00 117.00   0.50   10.00    --   49.31  22.00  65.00  134
  4  ω     -7.00  20.00   0.50   10.00    --   49.31 -22.00-100.00   54
  5  ω   -142.00 -89.00   0.50   10.00    --  -90.00 -22.00-100.00  106
  6  ω    102.00 156.00   0.50   10.00    --  106.00  22.00  65.00  108
  7  ω    -24.00  14.00   0.50   10.00    --  -49.31  19.00-150.00   76
  8  ω   -120.00 -95.00   0.50   10.00    --  -49.31 -57.00  90.00   50
  9  ω    -62.00 -23.00   0.50   10.00    --  -90.00  57.00  60.00   78
 10  ω   -142.00-102.00   0.50   10.00    --  -90.00 -99.00   0.00   80
 11  ω   -146.00 -94.00   0.50   10.00    --  -90.00 -57.00   0.00  104
 12  ω    -45.00 -19.00   0.50   10.00    --  -90.00  57.00-150.00   52
 13  ω    -79.00 -54.00   0.50   10.00    --  -90.00 125.00-180.00   50
 14  ω    -80.00 -54.00   0.50   10.00    --  -90.00 125.00 120.00   52
 15  ω    -56.00 -21.00   0.50   10.00    --  -90.00  57.00 -90.00   70
 16  ω     38.00  65.00   0.50   10.00    --  106.00 -57.00-180.00   54
 17  ω     40.00  66.00   0.50   10.00    --  106.00 -57.00  90.00   52
 18  ω     34.00  65.00   0.50   10.00    --  106.00 -57.00 -30.00   62
 19  ω     61.00 101.00   0.50   10.00    --  106.00 -99.00-180.00   80
 20  ω     69.00 112.00   0.50   10.00    --  106.00-125.00 150.00   86
 21  ω     34.00  60.00   0.50   10.00    --  106.00 -57.00 150.00   52
 22  ω     40.00  66.00   0.50   10.00    --  106.00 -57.00 -90.00   52
 23  ω     34.00  65.00   0.50   10.00    --  106.00 -57.00  60.00   62
 24  ω     34.00  59.00   0.50   10.00    --  106.00 -57.00   0.00   50
 25  ω     38.00  65.00   0.50   10.00    --  106.00 -57.00 120.00   54
 26  ω     36.00  63.00   0.50   10.00    --  106.00 -57.00 -60.00   54
 27  ω     37.00  65.00   0.50   10.00    --  106.00-125.00 150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1340423000
_diffrn_orient_matrix_UB_12      0.0493145000
_diffrn_orient_matrix_UB_13      -0.0011069000
_diffrn_orient_matrix_UB_21      0.0271410000
_diffrn_orient_matrix_UB_22      -0.0151202000
_diffrn_orient_matrix_UB_23      0.0656441000
_diffrn_orient_matrix_UB_31      0.0359283000
_diffrn_orient_matrix_UB_32      -0.1722328000
_diffrn_orient_matrix_UB_33      -0.0060876000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.370
_reflns_Friedel_fraction_full    0.426
_reflns_Friedel_fraction_max     0.426
_reflns_number_gt                4224
_reflns_number_total             5760
_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 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Flack x determined using 1172 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     566
_refine_ls_number_reflns         5760
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0800
_refine_ls_restrained_S_all      1.074
_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)+(0.1771P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2265
_refine_ls_wR_factor_ref         0.2489
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5A(H5AA), C6(H6), C8A(H8AA), C9(H9), C10(H10), C12(H12), C5AB(H5AB),
 C6B(H6B), C8AB(H8AB), C9B(H9B), C10B(H10B), C12B(H12B), N1D(H1D)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C17(H17A,H17B), C18(H18A,
 H18B), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C7B(H7BA,H7BB), C8B(H8BA,H8BB),
 C17B(H17C,H17D), C18B(H18C,H18D), C3D(H3DA,H3DB), C4D(H4DA,H4DB), C5D(H5DA,
 H5DB), C6D(H6DA,H6DB), C7D(H7DA,H7DB), C8D(H8DA,H8DB)
2.c Idealised Me refined as rotating group:
 C3M(H3MA,H3MB,H3MC), C6M(H6MA,H6MB,H6MC), C9M(H9MA,H9MB,H9MC), C3MB(H3MD,H3ME,
 H3MF), C6MB(H6MD,H6ME,H6MF), C9MB(H9MD,H9ME,H9MF)
2.d Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_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
O1 O 0.9873(5) 0.5085(7) 0.7245(2) 0.0641(15) Uani 1 1 d . . . . .
O2 O 0.9343(6) 0.6158(9) 0.6806(2) 0.0786(18) Uani 1 1 d . . . . .
C3 C 0.8059(9) 0.6381(13) 0.6856(3) 0.075(3) Uani 1 1 d . . . . .
C3M C 0.7629(10) 0.7614(13) 0.6419(4) 0.084(3) Uani 1 1 d . . . . .
H3MA H 0.814459 0.854305 0.649626 0.126 Uiso 1 1 calc R U . . .
H3MB H 0.677213 0.788183 0.644131 0.126 Uiso 1 1 calc R U . . .
H3MC H 0.769098 0.722101 0.603487 0.126 Uiso 1 1 calc R U . . .
C4 C 0.7872(9) 0.6792(13) 0.7463(3) 0.074(3) Uani 1 1 d . . . . .
H4A H 0.859632 0.738389 0.764924 0.088 Uiso 1 1 calc R U . . .
H4B H 0.714521 0.748039 0.744520 0.088 Uiso 1 1 calc R U . . .
C5 C 0.7697(9) 0.5452(12) 0.7815(3) 0.070(2) Uani 1 1 d . . . . .
H5A H 0.688356 0.500530 0.766154 0.084 Uiso 1 1 calc R U . . .
H5B H 0.763484 0.584921 0.820297 0.084 Uiso 1 1 calc R U . . .
C5A C 0.8608(7) 0.4103(10) 0.7891(3) 0.0552(19) Uani 1 1 d . . . . .
H5AA H 0.930882 0.445788 0.818180 0.066 Uiso 1 1 calc R U . . .
C6 C 0.8100(7) 0.2641(10) 0.8141(3) 0.057(2) Uani 1 1 d . . . . .
H6 H 0.734097 0.232345 0.787786 0.068 Uiso 1 1 calc R U . . .
C6M C 0.7729(8) 0.2978(13) 0.8729(3) 0.068(2) Uani 1 1 d . . . . .
H6MA H 0.846637 0.320120 0.900584 0.103 Uiso 1 1 calc R U . . .
H6MB H 0.730638 0.206976 0.885759 0.103 Uiso 1 1 calc R U . . .
H6MC H 0.717764 0.388012 0.870029 0.103 Uiso 1 1 calc R U . . .
C7 C 0.9001(7) 0.1306(10) 0.8172(3) 0.058(2) Uani 1 1 d . . . . .
H7A H 0.974445 0.157152 0.844609 0.070 Uiso 1 1 calc R U . . .
H7B H 0.862521 0.036968 0.831820 0.070 Uiso 1 1 calc R U . . .
C8 C 0.9368(8) 0.0939(10) 0.7600(3) 0.058(2) Uani 1 1 d . . . . .
H8A H 0.863153 0.065554 0.732479 0.070 Uiso 1 1 calc R U . . .
H8B H 0.993918 0.004178 0.763786 0.070 Uiso 1 1 calc R U . . .
C8A C 0.9992(7) 0.2349(10) 0.7379(3) 0.0523(18) Uani 1 1 d . . . . .
H8AA H 1.071258 0.259352 0.767742 0.063 Uiso 1 1 calc R U . . .
C9 C 1.0527(7) 0.2083(11) 0.6810(3) 0.057(2) Uani 1 1 d . . . . .
H9 H 1.099631 0.303692 0.673237 0.068 Uiso 1 1 calc R U . . .
C9M C 1.1400(9) 0.0701(11) 0.6845(3) 0.068(2) Uani 1 1 d . . . . .
H9MA H 1.197724 0.075228 0.720443 0.102 Uiso 1 1 calc R U . . .
H9MB H 1.185822 0.072824 0.652062 0.102 Uiso 1 1 calc R U . . .
H9MC H 1.092744 -0.026838 0.683415 0.102 Uiso 1 1 calc R U . . .
C10 C 0.9478(8) 0.1890(12) 0.6326(3) 0.063(2) Uani 1 1 d . . . . .
H10 H 0.901998 0.090033 0.636513 0.075 Uiso 1 1 calc R U . . .
O11 O 0.8654(5) 0.3243(10) 0.62892(19) 0.079(2) Uani 1 1 d . . . . .
C12 C 0.8169(9) 0.3623(12) 0.6802(3) 0.069(2) Uani 1 1 d . . . . .
H12 H 0.761024 0.275188 0.687554 0.082 Uiso 1 1 calc R U . . .
C12A C 0.9157(8) 0.3777(10) 0.7343(3) 0.0578(19) Uani 1 1 d . . . . .
O13 O 0.7428(6) 0.4965(9) 0.6681(3) 0.0822(19) Uani 1 1 d . . . . .
O14 O 0.9968(5) 0.1933(7) 0.57971(18) 0.0626(15) Uani 1 1 d . . . . .
C15 C 0.9298(8) 0.1207(11) 0.5334(3) 0.063(2) Uani 1 1 d . . . . .
O16 O 0.8334(6) 0.0558(9) 0.5360(2) 0.0767(19) Uani 1 1 d . . . . .
C17 C 0.9946(7) 0.1303(13) 0.4832(3) 0.064(2) Uani 1 1 d . . . . .
H17A H 1.060746 0.051224 0.486759 0.077 Uiso 1 1 calc R U . . .
H17B H 1.033002 0.234223 0.482091 0.077 Uiso 1 1 calc R U . . .
C18 C 0.9059(7) 0.1032(12) 0.4275(3) 0.064(2) Uani 1 1 d . . . . .
H18A H 0.954216 0.085693 0.395950 0.077 Uiso 1 1 calc R U . . .
H18B H 0.857459 0.007898 0.431528 0.077 Uiso 1 1 calc R U . . .
C19 C 0.8194(8) 0.2368(11) 0.4119(3) 0.060(2) Uani 1 1 d . . . . .
O20 O 0.8152(6) 0.3543(8) 0.4396(2) 0.0693(16) Uani 1 1 d . . . . .
O21 O 0.7389(5) 0.2061(8) 0.36396(18) 0.0667(16) Uani 1 1 d . . . . .
H21 H 0.694662 0.284658 0.355087 0.100 Uiso 1 1 calc R U . . .
O1B O 0.0967(4) 0.4626(6) -0.07953(19) 0.0485(12) Uani 1 1 d . . . . .
O2B O 0.0565(4) 0.5974(6) -0.04870(19) 0.0510(12) Uani 1 1 d . . . . .
C3B C 0.1018(6) 0.7375(10) -0.0708(3) 0.0522(18) Uani 1 1 d . . . . .
C3MB C 0.0414(7) 0.8664(11) -0.0427(3) 0.059(2) Uani 1 1 d . . . . .
H3MD H 0.048423 0.846027 -0.001541 0.089 Uiso 1 1 calc R U . . .
H3ME H -0.045684 0.872253 -0.059418 0.089 Uiso 1 1 calc R U . . .
H3MF H 0.081748 0.965282 -0.048925 0.089 Uiso 1 1 calc R U . . .
C4B C 0.0783(7) 0.7425(11) -0.1375(3) 0.059(2) Uani 1 1 d . . . . .
H4BA H 0.003216 0.681435 -0.151102 0.071 Uiso 1 1 calc R U . . .
H4BB H 0.061810 0.851638 -0.149720 0.071 Uiso 1 1 calc R U . . .
C5AB C 0.2243(6) 0.5115(10) -0.1515(3) 0.0501(18) Uani 1 1 d . . . . .
H5AB H 0.160980 0.442137 -0.173452 0.060 Uiso 1 1 calc R U . . .
C5B C 0.1812(7) 0.6812(11) -0.1664(3) 0.058(2) Uani 1 1 d . . . . .
H5BA H 0.252835 0.751152 -0.156753 0.070 Uiso 1 1 calc R U . . .
H5BB H 0.155038 0.687666 -0.208383 0.070 Uiso 1 1 calc R U . . .
C6B C 0.3431(7) 0.4778(12) -0.1739(3) 0.059(2) Uani 1 1 d . . . . .
H6B H 0.406246 0.554557 -0.156455 0.071 Uiso 1 1 calc R U . . .
C6MB C 0.3309(8) 0.4909(12) -0.2391(3) 0.066(2) Uani 1 1 d . . . . .
H6MD H 0.270131 0.415293 -0.256965 0.099 Uiso 1 1 calc R U . . .
H6ME H 0.410599 0.469524 -0.251195 0.099 Uiso 1 1 calc R U . . .
H6MF H 0.304084 0.596287 -0.251064 0.099 Uiso 1 1 calc R U . . .
C7B C 0.3892(8) 0.3139(11) -0.1565(3) 0.061(2) Uani 1 1 d . . . . .
H7BA H 0.469782 0.297187 -0.169280 0.073 Uiso 1 1 calc R U . . .
H7BB H 0.330823 0.236456 -0.176182 0.073 Uiso 1 1 calc R U . . .
C8AB C 0.2789(6) 0.3106(9) -0.0713(2) 0.0482(17) Uani 1 1 d . . . . .
H8AB H 0.221402 0.232503 -0.092213 0.058 Uiso 1 1 calc R U . . .
C8B C 0.4029(6) 0.2874(10) -0.0907(3) 0.0516(18) Uani 1 1 d . . . . .
H8BA H 0.433003 0.180513 -0.081216 0.062 Uiso 1 1 calc R U . . .
H8BB H 0.463279 0.361838 -0.070607 0.062 Uiso 1 1 calc R U . . .
C9B C 0.2806(7) 0.2821(10) -0.0073(3) 0.0515(19) Uani 1 1 d . . . . .
H9B H 0.194244 0.287495 0.000915 0.062 Uiso 1 1 calc R U . . .
C9MB C 0.3344(7) 0.1208(10) 0.0120(3) 0.057(2) Uani 1 1 d . . . . .
H9MD H 0.294449 0.040290 -0.013741 0.086 Uiso 1 1 calc R U . . .
H9ME H 0.319847 0.099807 0.051198 0.086 Uiso 1 1 calc R U . . .
H9MF H 0.423046 0.120272 0.010783 0.086 Uiso 1 1 calc R U . . .
C10B C 0.3540(7) 0.4097(10) 0.0256(2) 0.0497(18) Uani 1 1 d . . . . .
H10B H 0.442233 0.407009 0.020021 0.060 Uiso 1 1 calc R U . . .
O11B O 0.2991(5) 0.5598(6) 0.01117(18) 0.0526(13) Uani 1 1 d . . . . .
C12B C 0.2910(6) 0.5994(9) -0.0473(2) 0.0440(16) Uani 1 1 d . . . . .
H12B H 0.376092 0.612343 -0.056634 0.053 Uiso 1 1 calc R U . . .
C12C C 0.2241(6) 0.4735(10) -0.0871(3) 0.0471(17) Uani 1 1 d . . . . .
O13B O 0.2318(4) 0.7458(6) -0.05193(18) 0.0501(12) Uani 1 1 d . . . . .
O14B O 0.3412(4) 0.3990(7) 0.08563(17) 0.0524(13) Uani 1 1 d . . . . .
C15B C 0.4474(7) 0.3999(10) 0.1244(3) 0.0494(18) Uani 1 1 d . . . . .
O16B O 0.5462(5) 0.3815(9) 0.11120(19) 0.0717(18) Uani 1 1 d . . . . .
C17B C 0.4178(7) 0.4283(11) 0.1826(3) 0.058(2) Uani 1 1 d . . . . .
H17C H 0.344501 0.366088 0.187588 0.070 Uiso 1 1 calc R U . . .
H17D H 0.396211 0.539500 0.185812 0.070 Uiso 1 1 calc R U . . .
C18B C 0.5212(8) 0.3887(12) 0.2309(3) 0.065(2) Uani 1 1 d . . . . .
H18C H 0.600601 0.424704 0.220806 0.078 Uiso 1 1 calc R U . . .
H18D H 0.525778 0.274394 0.236264 0.078 Uiso 1 1 calc R U . . .
C19B C 0.4987(10) 0.4663(13) 0.2865(3) 0.081(3) Uani 1 1 d . . . . .
O20B O 0.4101(7) 0.5581(9) 0.2874(2) 0.093(2) Uani 1 1 d . . . . .
O21B O 0.5740(6) 0.4250(9) 0.3318(2) 0.083(2) Uani 1 1 d . . . . .
N1D N 0.5459(7) 0.6643(9) 0.4025(2) 0.066(2) Uani 1 1 d . . . . .
H1D H 0.557688 0.579466 0.374860 0.079 Uiso 1 1 calc R U . . .
N2D N 0.5155(7) 0.8799(11) 0.4717(3) 0.074(2) Uani 1 1 d . . . . .
C3D C 0.5551(9) 0.8182(15) 0.3748(3) 0.081(3) Uani 1 1 d . . . . .
H3DA H 0.488159 0.829748 0.341913 0.097 Uiso 1 1 calc R U . . .
H3DB H 0.634721 0.826929 0.360352 0.097 Uiso 1 1 calc R U . . .
C4D C 0.5450(10) 0.9438(13) 0.4186(4) 0.077(3) Uani 1 1 d . . . . .
H4DA H 0.623931 1.000924 0.426500 0.092 Uiso 1 1 calc R U . . .
H4DB H 0.480381 1.018816 0.402795 0.092 Uiso 1 1 calc R U . . .
C5D C 0.6455(8) 0.6554(14) 0.4538(3) 0.076(3) Uani 1 1 d . . . . .
H5DA H 0.726915 0.676251 0.442367 0.092 Uiso 1 1 calc R U . . .
H5DB H 0.647157 0.550881 0.471511 0.092 Uiso 1 1 calc R U . . .
C6D C 0.6143(9) 0.7805(13) 0.4960(3) 0.075(3) Uani 1 1 d . . . . .
H6DA H 0.591651 0.728745 0.530410 0.090 Uiso 1 1 calc R U . . .
H6DB H 0.688282 0.844731 0.508464 0.090 Uiso 1 1 calc R U . . .
C7D C 0.4231(8) 0.6463(11) 0.4219(3) 0.064(2) Uani 1 1 d . . . . .
H7DA H 0.421637 0.550096 0.444875 0.076 Uiso 1 1 calc R U . . .
H7DB H 0.357405 0.639068 0.388325 0.076 Uiso 1 1 calc R U . . .
C8D C 0.4020(8) 0.7895(14) 0.4583(3) 0.081(3) Uani 1 1 d . . . . .
H8DA H 0.336711 0.855551 0.437147 0.098 Uiso 1 1 calc R U . . .
H8DB H 0.374493 0.755281 0.494358 0.098 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
O1 O2 1.443(8) . ?
O1 C12A 1.412(10) . ?
O2 C3 1.449(12) . ?
C3 C3M 1.504(13) . ?
C3 C4 1.522(11) . ?
C3 O13 1.430(12) . ?
C3M H3MA 0.9800 . ?
C3M H3MB 0.9800 . ?
C3M H3MC 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.450(14) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C5A 1.525(12) . ?
C5A H5AA 1.0000 . ?
C5A C6 1.530(12) . ?
C5A C12A 1.533(10) . ?
C6 H6 1.0000 . ?
C6 C6M 1.534(11) . ?
C6 C7 1.511(12) . ?
C6M H6MA 0.9800 . ?
C6M H6MB 0.9800 . ?
C6M H6MC 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.500(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C8A 1.523(12) . ?
C8A H8AA 1.0000 . ?
C8A C9 1.564(10) . ?
C8A C12A 1.528(12) . ?
C9 H9 1.0000 . ?
C9 C9M 1.522(13) . ?
C9 C10 1.504(10) . ?
C9M H9MA 0.9800 . ?
C9M H9MB 0.9800 . ?
C9M H9MC 0.9800 . ?
C10 H10 1.0000 . ?
C10 O11 1.468(12) . ?
C10 O14 1.435(8) . ?
O11 C12 1.434(10) . ?
C12 H12 1.0000 . ?
C12 C12A 1.552(10) . ?
C12 O13 1.416(11) . ?
O14 C15 1.373(9) . ?
C15 O16 1.207(10) . ?
C15 C17 1.476(12) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.532(9) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.501(13) . ?
C19 O20 1.208(11) . ?
C19 O21 1.353(9) . ?
O21 H21 0.8400 . ?
O1B O2B 1.471(7) . ?
O1B C12C 1.443(8) . ?
O2B C3B 1.431(10) . ?
C3B C3MB 1.497(12) . ?
C3B C4B 1.558(9) . ?
C3B O13B 1.433(8) . ?
C3MB H3MD 0.9800 . ?
C3MB H3ME 0.9800 . ?
C3MB H3MF 0.9800 . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.504(12) . ?
C5AB H5AB 1.0000 . ?
C5AB C5B 1.557(12) . ?
C5AB C6B 1.510(11) . ?
C5AB C12C 1.556(9) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C6B H6B 1.0000 . ?
C6B C6MB 1.531(9) . ?
C6B C7B 1.532(13) . ?
C6MB H6MD 0.9800 . ?
C6MB H6ME 0.9800 . ?
C6MB H6MF 0.9800 . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C7B C8B 1.556(9) . ?
C8AB H8AB 1.0000 . ?
C8AB C8B 1.517(10) . ?
C8AB C9B 1.527(9) . ?
C8AB C12C 1.547(11) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C9B H9B 1.0000 . ?
C9B C9MB 1.548(12) . ?
C9B C10B 1.507(11) . ?
C9MB H9MD 0.9800 . ?
C9MB H9ME 0.9800 . ?
C9MB H9MF 0.9800 . ?
C10B H10B 1.0000 . ?
C10B O11B 1.443(10) . ?
C10B O14B 1.448(7) . ?
O11B C12B 1.412(8) . ?
C12B H12B 1.0000 . ?
C12B C12C 1.544(9) . ?
C12B O13B 1.413(9) . ?
O14B C15B 1.370(8) . ?
C15B O16B 1.186(9) . ?
C15B C17B 1.481(9) . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C17B C18B 1.522(9) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C18B C19B 1.527(12) . ?
C19B O20B 1.255(12) . ?
C19B O21B 1.299(10) . ?
N1D H1D 1.0000 . ?
N1D C3D 1.486(14) . ?
N1D C5D 1.507(9) . ?
N1D C7D 1.499(11) . ?
N2D C4D 1.450(12) . ?
N2D C6D 1.432(13) . ?
N2D C8D 1.464(12) . ?
C3D H3DA 0.9900 . ?
C3D H3DB 0.9900 . ?
C3D C4D 1.511(15) . ?
C4D H4DA 0.9900 . ?
C4D H4DB 0.9900 . ?
C5D H5DA 0.9900 . ?
C5D H5DB 0.9900 . ?
C5D C6D 1.541(14) . ?
C6D H6DA 0.9900 . ?
C6D H6DB 0.9900 . ?
C7D H7DA 0.9900 . ?
C7D H7DB 0.9900 . ?
C7D C8D 1.539(14) . ?
C8D H8DA 0.9900 . ?
C8D H8DB 0.9900 . ?

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
C12A O1 O2 116.9(6) . . ?
O1 O2 C3 108.5(6) . . ?
O2 C3 C3M 104.2(8) . . ?
O2 C3 C4 112.4(7) . . ?
C3M C3 C4 114.2(9) . . ?
O13 C3 O2 107.5(8) . . ?
O13 C3 C3M 108.3(7) . . ?
O13 C3 C4 109.9(8) . . ?
C3 C3M H3MA 109.5 . . ?
C3 C3M H3MB 109.5 . . ?
C3 C3M H3MC 109.5 . . ?
H3MA C3M H3MB 109.5 . . ?
H3MA C3M H3MC 109.5 . . ?
H3MB C3M H3MC 109.5 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 C3 113.8(9) . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C4 C5 H5A 106.9 . . ?
C4 C5 H5B 106.9 . . ?
C4 C5 C5A 121.9(8) . . ?
H5A C5 H5B 106.7 . . ?
C5A C5 H5A 106.9 . . ?
C5A C5 H5B 106.9 . . ?
C5 C5A H5AA 105.9 . . ?
C5 C5A C6 113.4(7) . . ?
C5 C5A C12A 112.1(6) . . ?
C6 C5A H5AA 105.9 . . ?
C6 C5A C12A 112.9(7) . . ?
C12A C5A H5AA 105.9 . . ?
C5A C6 H6 107.6 . . ?
C5A C6 C6M 111.0(7) . . ?
C6M C6 H6 107.6 . . ?
C7 C6 C5A 111.5(6) . . ?
C7 C6 H6 107.6 . . ?
C7 C6 C6M 111.3(6) . . ?
C6 C6M H6MA 109.5 . . ?
C6 C6M H6MB 109.5 . . ?
C6 C6M H6MC 109.5 . . ?
H6MA C6M H6MB 109.5 . . ?
H6MA C6M H6MC 109.5 . . ?
H6MB C6M H6MC 109.5 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C6 112.4(6) . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C7 C8 C8A 109.9(7) . . ?
H8A C8 H8B 108.2 . . ?
C8A C8 H8A 109.7 . . ?
C8A C8 H8B 109.7 . . ?
C8 C8A H8AA 106.0 . . ?
C8 C8A C9 115.3(7) . . ?
C8 C8A C12A 111.0(6) . . ?
C9 C8A H8AA 106.0 . . ?
C12A C8A H8AA 106.0 . . ?
C12A C8A C9 111.8(6) . . ?
C8A C9 H9 108.1 . . ?
C9M C9 C8A 112.5(6) . . ?
C9M C9 H9 108.1 . . ?
C10 C9 C8A 108.8(6) . . ?
C10 C9 H9 108.1 . . ?
C10 C9 C9M 111.2(7) . . ?
C9 C9M H9MA 109.5 . . ?
C9 C9M H9MB 109.5 . . ?
C9 C9M H9MC 109.5 . . ?
H9MA C9M H9MB 109.5 . . ?
H9MA C9M H9MC 109.5 . . ?
H9MB C9M H9MC 109.5 . . ?
C9 C10 H10 111.3 . . ?
O11 C10 C9 110.7(7) . . ?
O11 C10 H10 111.3 . . ?
O14 C10 C9 108.1(6) . . ?
O14 C10 H10 111.3 . . ?
O14 C10 O11 103.8(6) . . ?
C12 O11 C10 115.8(6) . . ?
O11 C12 H12 107.1 . . ?
O11 C12 C12A 114.3(7) . . ?
C12A C12 H12 107.1 . . ?
O13 C12 O11 107.0(7) . . ?
O13 C12 H12 107.1 . . ?
O13 C12 C12A 114.0(7) . . ?
O1 C12A C5A 107.1(6) . . ?
O1 C12A C8A 107.6(6) . . ?
O1 C12A C12 105.7(7) . . ?
C5A C12A C12 113.1(7) . . ?
C8A C12A C5A 114.3(6) . . ?
C8A C12A C12 108.5(7) . . ?
C12 O13 C3 113.3(7) . . ?
C15 O14 C10 117.0(7) . . ?
O14 C15 C17 110.3(8) . . ?
O16 C15 O14 122.6(7) . . ?
O16 C15 C17 127.0(7) . . ?
C15 C17 H17A 109.4 . . ?
C15 C17 H17B 109.4 . . ?
C15 C17 C18 111.0(7) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C17 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 C17 113.1(8) . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
O20 C19 C18 125.6(6) . . ?
O20 C19 O21 122.8(8) . . ?
O21 C19 C18 111.5(7) . . ?
C19 O21 H21 109.5 . . ?
C12C O1B O2B 112.4(5) . . ?
C3B O2B O1B 109.5(4) . . ?
O2B C3B C3MB 105.0(6) . . ?
O2B C3B C4B 112.2(6) . . ?
O2B C3B O13B 108.4(6) . . ?
C3MB C3B C4B 114.2(7) . . ?
O13B C3B C3MB 108.4(6) . . ?
O13B C3B C4B 108.5(6) . . ?
C3B C3MB H3MD 109.5 . . ?
C3B C3MB H3ME 109.5 . . ?
C3B C3MB H3MF 109.5 . . ?
H3MD C3MB H3ME 109.5 . . ?
H3MD C3MB H3MF 109.5 . . ?
H3ME C3MB H3MF 109.5 . . ?
C3B C4B H4BA 108.4 . . ?
C3B C4B H4BB 108.4 . . ?
H4BA C4B H4BB 107.5 . . ?
C5B C4B C3B 115.4(6) . . ?
C5B C4B H4BA 108.4 . . ?
C5B C4B H4BB 108.4 . . ?
C5B C5AB H5AB 106.1 . . ?
C6B C5AB H5AB 106.1 . . ?
C6B C5AB C5B 110.5(7) . . ?
C6B C5AB C12C 115.6(6) . . ?
C12C C5AB H5AB 106.1 . . ?
C12C C5AB C5B 111.9(6) . . ?
C4B C5B C5AB 116.7(7) . . ?
C4B C5B H5BA 108.1 . . ?
C4B C5B H5BB 108.1 . . ?
C5AB C5B H5BA 108.1 . . ?
C5AB C5B H5BB 108.1 . . ?
H5BA C5B H5BB 107.3 . . ?
C5AB C6B H6B 108.3 . . ?
C5AB C6B C6MB 113.0(7) . . ?
C5AB C6B C7B 110.6(7) . . ?
C6MB C6B H6B 108.3 . . ?
C6MB C6B C7B 108.2(7) . . ?
C7B C6B H6B 108.3 . . ?
C6B C6MB H6MD 109.5 . . ?
C6B C6MB H6ME 109.5 . . ?
C6B C6MB H6MF 109.5 . . ?
H6MD C6MB H6ME 109.5 . . ?
H6MD C6MB H6MF 109.5 . . ?
H6ME C6MB H6MF 109.5 . . ?
C6B C7B H7BA 109.1 . . ?
C6B C7B H7BB 109.1 . . ?
C6B C7B C8B 112.3(6) . . ?
H7BA C7B H7BB 107.9 . . ?
C8B C7B H7BA 109.1 . . ?
C8B C7B H7BB 109.1 . . ?
C8B C8AB H8AB 107.0 . . ?
C8B C8AB C9B 113.6(5) . . ?
C8B C8AB C12C 112.4(6) . . ?
C9B C8AB H8AB 107.0 . . ?
C9B C8AB C12C 109.3(6) . . ?
C12C C8AB H8AB 107.0 . . ?
C7B C8B H8BA 109.9 . . ?
C7B C8B H8BB 109.9 . . ?
C8AB C8B C7B 109.1(6) . . ?
C8AB C8B H8BA 109.9 . . ?
C8AB C8B H8BB 109.9 . . ?
H8BA C8B H8BB 108.3 . . ?
C8AB C9B H9B 108.4 . . ?
C8AB C9B C9MB 112.5(6) . . ?
C9MB C9B H9B 108.4 . . ?
C10B C9B C8AB 108.6(6) . . ?
C10B C9B H9B 108.4 . . ?
C10B C9B C9MB 110.4(5) . . ?
C9B C9MB H9MD 109.5 . . ?
C9B C9MB H9ME 109.5 . . ?
C9B C9MB H9MF 109.5 . . ?
H9MD C9MB H9ME 109.5 . . ?
H9MD C9MB H9MF 109.5 . . ?
H9ME C9MB H9MF 109.5 . . ?
C9B C10B H10B 111.7 . . ?
O11B C10B C9B 110.8(5) . . ?
O11B C10B H10B 111.7 . . ?
O11B C10B O14B 100.9(5) . . ?
O14B C10B C9B 109.6(6) . . ?
O14B C10B H10B 111.7 . . ?
C12B O11B C10B 114.1(5) . . ?
O11B C12B H12B 108.7 . . ?
O11B C12B C12C 112.3(6) . . ?
O11B C12B O13B 104.5(5) . . ?
C12C C12B H12B 108.7 . . ?
O13B C12B H12B 108.7 . . ?
O13B C12B C12C 113.8(5) . . ?
O1B C12C C5AB 106.3(5) . . ?
O1B C12C C8AB 105.2(6) . . ?
O1B C12C C12B 110.6(6) . . ?
C8AB C12C C5AB 111.6(6) . . ?
C12B C12C C5AB 112.1(6) . . ?
C12B C12C C8AB 110.7(5) . . ?
C12B O13B C3B 114.0(6) . . ?
C15B O14B C10B 116.9(5) . . ?
O14B C15B C17B 109.6(6) . . ?
O16B C15B O14B 123.2(6) . . ?
O16B C15B C17B 127.2(6) . . ?
C15B C17B H17C 108.6 . . ?
C15B C17B H17D 108.6 . . ?
C15B C17B C18B 114.5(7) . . ?
H17C C17B H17D 107.6 . . ?
C18B C17B H17C 108.6 . . ?
C18B C17B H17D 108.6 . . ?
C17B C18B H18C 109.6 . . ?
C17B C18B H18D 109.6 . . ?
C17B C18B C19B 110.3(7) . . ?
H18C C18B H18D 108.1 . . ?
C19B C18B H18C 109.6 . . ?
C19B C18B H18D 109.6 . . ?
O20B C19B C18B 121.1(7) . . ?
O20B C19B O21B 123.9(8) . . ?
O21B C19B C18B 115.0(9) . . ?
C3D N1D H1D 109.7 . . ?
C3D N1D C5D 108.0(7) . . ?
C3D N1D C7D 110.6(7) . . ?
C5D N1D H1D 109.7 . . ?
C7D N1D H1D 109.7 . . ?
C7D N1D C5D 109.2(6) . . ?
C4D N2D C8D 108.1(7) . . ?
C6D N2D C4D 108.5(7) . . ?
C6D N2D C8D 109.9(8) . . ?
N1D C3D H3DA 110.0 . . ?
N1D C3D H3DB 110.0 . . ?
N1D C3D C4D 108.4(6) . . ?
H3DA C3D H3DB 108.4 . . ?
C4D C3D H3DA 110.0 . . ?
C4D C3D H3DB 110.0 . . ?
N2D C4D C3D 111.8(9) . . ?
N2D C4D H4DA 109.3 . . ?
N2D C4D H4DB 109.3 . . ?
C3D C4D H4DA 109.3 . . ?
C3D C4D H4DB 109.3 . . ?
H4DA C4D H4DB 107.9 . . ?
N1D C5D H5DA 110.5 . . ?
N1D C5D H5DB 110.5 . . ?
N1D C5D C6D 106.2(8) . . ?
H5DA C5D H5DB 108.7 . . ?
C6D C5D H5DA 110.5 . . ?
C6D C5D H5DB 110.5 . . ?
N2D C6D C5D 112.7(6) . . ?
N2D C6D H6DA 109.0 . . ?
N2D C6D H6DB 109.0 . . ?
C5D C6D H6DA 109.0 . . ?
C5D C6D H6DB 109.0 . . ?
H6DA C6D H6DB 107.8 . . ?
N1D C7D H7DA 110.1 . . ?
N1D C7D H7DB 110.1 . . ?
N1D C7D C8D 107.9(7) . . ?
H7DA C7D H7DB 108.4 . . ?
C8D C7D H7DA 110.1 . . ?
C8D C7D H7DB 110.1 . . ?
N2D C8D C7D 110.4(8) . . ?
N2D C8D H8DA 109.6 . . ?
N2D C8D H8DB 109.6 . . ?
C7D C8D H8DA 109.6 . . ?
C7D C8D H8DB 109.6 . . ?
H8DA C8D H8DB 108.1 . . ?

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 O2 C3 C3M 175.0(6) . . . . ?
O1 O2 C3 C4 50.9(10) . . . . ?
O1 O2 C3 O13 -70.2(7) . . . . ?
O2 O1 C12A C5A -102.8(7) . . . . ?
O2 O1 C12A C8A 133.9(6) . . . . ?
O2 O1 C12A C12 18.1(9) . . . . ?
O2 C3 C4 C5 -90.3(11) . . . . ?
O2 C3 O13 C12 31.2(9) . . . . ?
C3 C4 C5 C5A 53.6(11) . . . . ?
C3M C3 C4 C5 151.3(9) . . . . ?
C3M C3 O13 C12 143.3(9) . . . . ?
C4 C3 O13 C12 -91.4(9) . . . . ?
C4 C5 C5A C6 -164.9(8) . . . . ?
C4 C5 C5A C12A -35.5(11) . . . . ?
C5 C5A C6 C6M -59.1(8) . . . . ?
C5 C5A C6 C7 176.3(6) . . . . ?
C5 C5A C12A O1 65.9(8) . . . . ?
C5 C5A C12A C8A -175.0(7) . . . . ?
C5 C5A C12A C12 -50.2(10) . . . . ?
C5A C6 C7 C8 -56.1(8) . . . . ?
C6 C5A C12A O1 -164.5(6) . . . . ?
C6 C5A C12A C8A -45.4(8) . . . . ?
C6 C5A C12A C12 79.4(8) . . . . ?
C6 C7 C8 C8A 60.9(8) . . . . ?
C6M C6 C7 C8 179.4(7) . . . . ?
C7 C8 C8A C9 174.9(6) . . . . ?
C7 C8 C8A C12A -56.6(8) . . . . ?
C8 C8A C9 C9M -54.1(9) . . . . ?
C8 C8A C9 C10 69.5(9) . . . . ?
C8 C8A C12A O1 168.7(5) . . . . ?
C8 C8A C12A C5A 49.9(8) . . . . ?
C8 C8A C12A C12 -77.3(8) . . . . ?
C8A C9 C10 O11 56.6(9) . . . . ?
C8A C9 C10 O14 169.6(7) . . . . ?
C9 C8A C12A O1 -60.9(7) . . . . ?
C9 C8A C12A C5A -179.8(6) . . . . ?
C9 C8A C12A C12 53.0(9) . . . . ?
C9 C10 O11 C12 -55.3(10) . . . . ?
C9 C10 O14 C15 155.6(8) . . . . ?
C9M C9 C10 O11 -179.0(7) . . . . ?
C9M C9 C10 O14 -65.9(9) . . . . ?
C10 O11 C12 C12A 51.6(11) . . . . ?
C10 O11 C12 O13 178.8(7) . . . . ?
C10 O14 C15 O16 0.2(13) . . . . ?
C10 O14 C15 C17 -177.8(8) . . . . ?
O11 C10 O14 C15 -86.8(8) . . . . ?
O11 C12 C12A O1 65.9(9) . . . . ?
O11 C12 C12A C5A -177.2(8) . . . . ?
O11 C12 C12A C8A -49.2(10) . . . . ?
O11 C12 O13 C3 -96.2(8) . . . . ?
C12A O1 O2 C3 42.1(9) . . . . ?
C12A C5A C6 C6M 172.0(6) . . . . ?
C12A C5A C6 C7 47.3(8) . . . . ?
C12A C8A C9 C9M 177.8(7) . . . . ?
C12A C8A C9 C10 -58.5(9) . . . . ?
C12A C12 O13 C3 31.1(11) . . . . ?
O13 C3 C4 C5 29.4(11) . . . . ?
O13 C12 C12A O1 -57.5(10) . . . . ?
O13 C12 C12A C5A 59.5(11) . . . . ?
O13 C12 C12A C8A -172.6(7) . . . . ?
O14 C10 O11 C12 -171.1(7) . . . . ?
O14 C15 C17 C18 -160.2(8) . . . . ?
C15 C17 C18 C19 71.9(11) . . . . ?
O16 C15 C17 C18 21.8(14) . . . . ?
C17 C18 C19 O20 -1.3(12) . . . . ?
C17 C18 C19 O21 -177.2(7) . . . . ?
O1B O2B C3B C3MB 172.2(5) . . . . ?
O1B O2B C3B C4B 47.6(7) . . . . ?
O1B O2B C3B O13B -72.2(6) . . . . ?
O2B O1B C12C C5AB -106.8(6) . . . . ?
O2B O1B C12C C8AB 134.7(5) . . . . ?
O2B O1B C12C C12B 15.1(7) . . . . ?
O2B C3B C4B C5B -92.6(8) . . . . ?
O2B C3B O13B C12B 33.6(7) . . . . ?
C3B C4B C5B C5AB 56.5(10) . . . . ?
C3MB C3B C4B C5B 148.1(8) . . . . ?
C3MB C3B O13B C12B 147.0(6) . . . . ?
C4B C3B O13B C12B -88.5(7) . . . . ?
C5AB C6B C7B C8B -54.9(8) . . . . ?
C5B C5AB C6B C6MB -61.6(8) . . . . ?
C5B C5AB C6B C7B 177.0(5) . . . . ?
C5B C5AB C12C O1B 71.4(7) . . . . ?
C5B C5AB C12C C8AB -174.4(6) . . . . ?
C5B C5AB C12C C12B -49.6(8) . . . . ?
C6B C5AB C5B C4B -168.5(6) . . . . ?
C6B C5AB C12C O1B -161.0(7) . . . . ?
C6B C5AB C12C C8AB -46.8(9) . . . . ?
C6B C5AB C12C C12B 78.0(9) . . . . ?
C6B C7B C8B C8AB 59.7(9) . . . . ?
C6MB C6B C7B C8B -179.1(7) . . . . ?
C8AB C9B C10B O11B 60.7(8) . . . . ?
C8AB C9B C10B O14B 171.2(6) . . . . ?
C8B C8AB C9B C9MB -53.5(9) . . . . ?
C8B C8AB C9B C10B 68.9(8) . . . . ?
C8B C8AB C12C O1B 165.7(5) . . . . ?
C8B C8AB C12C C5AB 50.8(7) . . . . ?
C8B C8AB C12C C12B -74.8(7) . . . . ?
C9B C8AB C8B C7B 178.1(7) . . . . ?
C9B C8AB C12C O1B -67.2(6) . . . . ?
C9B C8AB C12C C5AB 178.0(6) . . . . ?
C9B C8AB C12C C12B 52.4(7) . . . . ?
C9B C10B O11B C12B -60.1(7) . . . . ?
C9B C10B O14B C15B 129.4(7) . . . . ?
C9MB C9B C10B O11B -175.6(6) . . . . ?
C9MB C9B C10B O14B -65.1(8) . . . . ?
C10B O11B C12B C12C 54.3(7) . . . . ?
C10B O11B C12B O13B 178.1(5) . . . . ?
C10B O14B C15B O16B -13.6(12) . . . . ?
C10B O14B C15B C17B 165.8(7) . . . . ?
O11B C10B O14B C15B -113.7(7) . . . . ?
O11B C12B C12C O1B 65.9(7) . . . . ?
O11B C12B C12C C5AB -175.6(6) . . . . ?
O11B C12B C12C C8AB -50.3(8) . . . . ?
O11B C12B O13B C3B -96.6(6) . . . . ?
C12C O1B O2B C3B 44.1(6) . . . . ?
C12C C5AB C5B C4B -38.2(8) . . . . ?
C12C C5AB C6B C6MB 170.1(7) . . . . ?
C12C C5AB C6B C7B 48.7(8) . . . . ?
C12C C8AB C8B C7B -57.1(8) . . . . ?
C12C C8AB C9B C9MB 180.0(6) . . . . ?
C12C C8AB C9B C10B -57.6(7) . . . . ?
C12C C12B O13B C3B 26.3(8) . . . . ?
O13B C3B C4B C5B 27.1(10) . . . . ?
O13B C12B C12C O1B -52.5(8) . . . . ?
O13B C12B C12C C5AB 66.0(8) . . . . ?
O13B C12B C12C C8AB -168.7(6) . . . . ?
O14B C10B O11B C12B -176.1(5) . . . . ?
O14B C15B C17B C18B 164.1(7) . . . . ?
C15B C17B C18B C19B 162.6(8) . . . . ?
O16B C15B C17B C18B -16.5(14) . . . . ?
C17B C18B C19B O20B -5.0(14) . . . . ?
C17B C18B C19B O21B 172.3(9) . . . . ?
N1D C3D C4D N2D -6.6(11) . . . . ?
N1D C5D C6D N2D -8.8(11) . . . . ?
N1D C7D C8D N2D -11.1(10) . . . . ?
C3D N1D C5D C6D 65.1(9) . . . . ?
C3D N1D C7D C8D -52.1(8) . . . . ?
C4D N2D C6D C5D -53.6(11) . . . . ?
C4D N2D C8D C7D 66.0(10) . . . . ?
C5D N1D C3D C4D -56.9(10) . . . . ?
C5D N1D C7D C8D 66.6(9) . . . . ?
C6D N2D C4D C3D 63.1(10) . . . . ?
C6D N2D C8D C7D -52.2(9) . . . . ?
C7D N1D C3D C4D 62.5(8) . . . . ?
C7D N1D C5D C6D -55.2(10) . . . . ?
C8D N2D C4D C3D -56.0(11) . . . . ?
C8D N2D C6D C5D 64.4(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.980
_oxdiff_exptl_absorpt_empirical_full_min 0.474

_vrf_PLAT340_ATS2-DABCO-2        
;
PROBLEM: Low Bond Precision on
 C-C Bonds ...............
RESPONSE: Crystals are very thin plates with a strong tendency to aggregate.
Overall data quality is consequently not great (Rint > 0.7).
;
_vrf_PLAT915_ATS2-DABCO-2        
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage
RESPONSE: Known correct absolute structure used.
;
####################################################################### 
# 
# 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_ATS-PHEN
_database_code_depnum_ccdc_archive 'CCDC 2427256'
loop_
_audit_author_name
_audit_author_address
'Laszlo Fabian'
;University of East Anglia
United Kingdom
;
_audit_update_record             
;
2025-02-26 deposited with the CCDC.	2025-10-15 downloaded from the CCDC.
;
_audit_creation_date             2023-09-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec141 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'artesunate 1,10-phenanthroline'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H28 O8, C12 H8 N2'
_chemical_formula_sum            'C31 H36 N2 O8'
_chemical_formula_weight         564.62
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C31 H36 N2 O8'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           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                   9.57054(18)
_cell_length_b                   51.5305(6)
_cell_length_c                   9.8305(2)
_cell_angle_alpha                90
_cell_angle_beta                 118.766(3)
_cell_angle_gamma                90
_cell_volume                     4249.88(16)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    16423
_cell_measurement_temperature    99.98(11)
_cell_measurement_theta_max      76.8270
_cell_measurement_theta_min      3.4210
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.815
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.462
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 4 0 0.0726
-1 3 0 0.1313
1 4 0 0.0660
-1 4 2 0.0910
0 -2 -1 0.0748
-2 1 1 0.0938
-1 -4 0 0.1043
1 -4 -1 0.0815
-1 -4 1 0.0718
2 -3 -3 0.0228
0 4 0 0.1158
1 3 0 0.0349
0 -1 0 0.0916
1 -4 1 0.1248

_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0002 4.0002 0.4994 0.0031 -0.0351 -0.1450
-1.0016 3.0117 0.0015 0.1258 0.1521 -0.0541
1.0016 3.9882 0.4982 -0.1345 -0.1536 -0.1733
-0.9997 4.0140 1.9976 0.1967 -0.1561 -0.2225
-0.0014 -2.0016 -1.4972 -0.0482 0.2172 0.1606
-2.0013 1.0257 1.4994 0.3272 0.0087 -0.0766
-1.0011 -3.9876 0.0007 0.1532 0.0738 0.1381
1.0012 -4.0122 -0.5006 -0.1406 -0.0834 0.1168
-1.0001 -3.9864 0.9987 0.1905 -0.0859 0.0676
2.0000 -3.0273 -2.9966 -0.3755 0.2084 0.2372
-0.0008 3.9990 -0.4985 -0.0343 0.1245 -0.0746
1.0006 2.9871 -0.4998 -0.1680 -0.0052 -0.0754
0.0001 -0.9999 -0.0001 0.0039 -0.0112 0.0275
1.0027 -4.0103 0.9964 -0.0846 -0.3229 0.0111

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -64
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23260
_diffrn_reflns_point_group_measured_fraction_full 0.655
_diffrn_reflns_point_group_measured_fraction_max 0.598
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.294
_diffrn_reflns_theta_min         3.431
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00 -72.00   0.50    0.82    --  -47.29-129.00 -22.00   92
  2  ω    -32.00  -4.00   0.50    0.82    --  -47.29  31.00-170.00   56
  3  ω   -165.00-122.00   0.50    3.30    --  -91.75 -31.00  29.00   86
  4  ω    -57.00 -21.00   0.50    3.30    --  -91.75  92.00 -20.00   72
  5  ω     51.00 118.00   0.50    3.30    --  106.64-140.00 164.00  134
  6  ω    -17.00   9.00   0.50    0.82    --  -47.29  19.00 -90.00   52
  7  ω   -118.00 -63.00   0.50    0.82    --  -47.29-140.00 164.00  110
  8  ω    -18.00  18.00   0.50    0.82    --   47.29 -19.00 -30.00   72
  9  ω    -51.00 -26.00   0.50    3.30    --  -91.75  45.00-120.00   50
 10  ω    -46.00 -20.00   0.50    3.30    --  -91.75  45.00 -30.00   52
 11  ω    -62.00 -36.00   0.50    3.30    --  -91.75  61.00  90.00   52
 12  ω   -160.00-106.00   0.50    3.30    --  -91.75 -77.00 -90.00  108
 13  ω    -71.00 -20.00   0.50    3.30    --  -91.75  61.00 -90.00  102
 14  ω    -50.00 -23.00   0.50    3.30    --  -91.75  45.00 -90.00   54
 15  ω    -68.00 -30.00   0.50    3.30    --  -91.75  61.00   0.00   76
 16  ω    144.00 171.00   0.50    3.30    --  106.64  77.00-150.00   54
 17  ω    107.00 132.00   0.50    3.30    --  106.64  77.00-150.00   50
 18  ω     39.00  64.00   0.50    3.30    --  106.64 -61.00   0.00   50
 19  ω     61.00  99.00   0.50    3.30    --  106.64 -77.00 -90.00   76
 20  ω     39.00  64.00   0.50    3.30    --  106.64 -61.00 120.00   50
 21  ω     44.00  91.00   0.50    3.30    --  106.64 -77.00-120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1373632000
_diffrn_orient_matrix_UB_12      -0.0039223000
_diffrn_orient_matrix_UB_13      0.0375864000
_diffrn_orient_matrix_UB_21      -0.1184114000
_diffrn_orient_matrix_UB_22      0.0111862000
_diffrn_orient_matrix_UB_23      -0.1598890000
_diffrn_orient_matrix_UB_31      -0.0286365000
_diffrn_orient_matrix_UB_32      -0.0274509000
_diffrn_orient_matrix_UB_33      -0.0705460000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.345
_reflns_Friedel_fraction_full    0.350
_reflns_Friedel_fraction_max     0.310
_reflns_number_gt                10239
_reflns_number_total             10786
_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 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 2414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1120
_refine_ls_number_reflns         10786
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.052
_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)+(0.0761P)²+0.7331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1220
_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:
 C5A(H5AA), C6(H6), C8A(H8AA), C9(H9), C10(H10), C12(H12), C5AB(H5AB),
 C6B(H6B), C8AB(H8AB), C9B(H9B), C10B(H10B), C12B(H12B), C5AD(H5AD), C6D(H6D),
 C8AD(H8AD), C9D(H9D), C10D(H10D), C12D(H12D)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C17(H17A,H17B), C18(H18A,
 H18B), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C7B(H7BA,H7BB), C8B(H8BA,H8BB),
 C17B(H17C,H17D), C18B(H18C,H18D), C4D(H4DA,H4DB), C5D(H5DA,H5DB), C7D(H7DA,
 H7DB), C8D(H8DA,H8DB), C17D(H17E,H17F), C18D(H18E,H18F)
2.c Aromatic/amide H refined with riding coordinates:
 C2P(H2P), C3P(H3P), C4P(H4P), C5P(H5P), C6P(H6P), C7P(H7P), C8P(H8P),
 C9P(H9P), C2Q(H2Q), C3Q(H3Q), C4Q(H4Q), C5Q(H5Q), C6Q(H6Q), C7Q(H7Q), C8Q(H8Q),
  C9Q(H9Q), C2R(H2R), C3R(H3R), C4R(H4R), C5R(H5R), C6R(H6R), C7R(H7R),
 C8R(H8R), C9R(H9R)
2.d Idealised Me refined as rotating group:
 C3M(H3MA,H3MB,H3MC), C6M(H6MA,H6MB,H6MC), C9M(H9MA,H9MB,H9MC), C3MB(H3MD,H3ME,
 H3MF), C6MB(H6MD,H6ME,H6MF), C9MB(H9MD,H9ME,H9MF), C3MD(H3MG,H3MH,H3MI),
 C6MD(H6MG,H6MH,H6MI), C9MD(H9MG,H9MH,H9MI)
2.e Idealised tetrahedral OH refined as rotating group:
 O21(H21), O21B(H21B), O21D(H21D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2476(3) 0.70056(5) -0.1181(3) 0.0437(6) Uani 1 1 d . . . . .
O2 O 0.2965(3) 0.72796(5) -0.0875(4) 0.0471(7) Uani 1 1 d . . . . .
C3 C 0.4636(5) 0.72913(7) -0.0170(5) 0.0464(9) Uani 1 1 d . . . . .
C3M C 0.4991(6) 0.75809(8) -0.0101(7) 0.0604(12) Uani 1 1 d . . . . .
H3MA H 0.613638 0.760993 0.055923 0.091 Uiso 1 1 calc R U . . .
H3MB H 0.440024 0.767348 0.033226 0.091 Uiso 1 1 calc R U . . .
H3MC H 0.466474 0.764532 -0.114925 0.091 Uiso 1 1 calc R U . . .
C4 C 0.5320(5) 0.71331(8) -0.1017(5) 0.0492(9) Uani 1 1 d . . . . .
H4A H 0.624623 0.722706 -0.096596 0.059 Uiso 1 1 calc R U . . .
H4B H 0.450513 0.711955 -0.212409 0.059 Uiso 1 1 calc R U . . .
C5 C 0.5846(5) 0.68609(7) -0.0372(5) 0.0416(8) Uani 1 1 d . . . . .
H5A H 0.674111 0.687617 0.069887 0.050 Uiso 1 1 calc R U . . .
H5B H 0.626064 0.677296 -0.100047 0.050 Uiso 1 1 calc R U . . .
C5A C 0.4566(4) 0.66872(7) -0.0334(4) 0.0356(7) Uani 1 1 d . . . . .
H5AA H 0.387550 0.662640 -0.142268 0.043 Uiso 1 1 calc R U . . .
C6 C 0.5293(4) 0.64418(7) 0.0650(4) 0.0356(7) Uani 1 1 d . . . . .
H6 H 0.605914 0.649640 0.173341 0.043 Uiso 1 1 calc R U . . .
C6M C 0.6208(5) 0.62808(8) 0.0013(5) 0.0448(9) Uani 1 1 d . . . . .
H6MA H 0.552233 0.625051 -0.109972 0.067 Uiso 1 1 calc R U . . .
H6MB H 0.651832 0.611396 0.055656 0.067 Uiso 1 1 calc R U . . .
H6MC H 0.716404 0.637559 0.017671 0.067 Uiso 1 1 calc R U . . .
C7 C 0.4023(4) 0.62746(7) 0.0698(4) 0.0367(8) Uani 1 1 d . . . . .
H7A H 0.453055 0.612276 0.137548 0.044 Uiso 1 1 calc R U . . .
H7B H 0.329559 0.620957 -0.035863 0.044 Uiso 1 1 calc R U . . .
C8 C 0.3061(4) 0.64242(7) 0.1305(5) 0.0395(8) Uani 1 1 d . . . . .
H8A H 0.377480 0.648277 0.238025 0.047 Uiso 1 1 calc R U . . .
H8B H 0.223994 0.630921 0.131951 0.047 Uiso 1 1 calc R U . . .
C8A C 0.2256(4) 0.66605(7) 0.0265(5) 0.0376(8) Uani 1 1 d . . . . .
H8AA H 0.152329 0.659324 -0.079918 0.045 Uiso 1 1 calc R U . . .
C9 C 0.1233(4) 0.68175(8) 0.0793(6) 0.0472(10) Uani 1 1 d . . . . .
H9 H 0.061715 0.694857 -0.003040 0.057 Uiso 1 1 calc R U . . .
C9M C 0.0035(6) 0.66488(10) 0.1000(9) 0.0713(17) Uani 1 1 d . . . . .
H9MA H -0.063240 0.655476 0.003410 0.107 Uiso 1 1 calc R U . . .
H9MB H -0.063937 0.675912 0.125666 0.107 Uiso 1 1 calc R U . . .
H9MC H 0.060864 0.652424 0.184142 0.107 Uiso 1 1 calc R U . . .
C10 C 0.2304(4) 0.69621(7) 0.2254(5) 0.0431(9) Uani 1 1 d . . . . .
H10 H 0.292363 0.683916 0.312679 0.052 Uiso 1 1 calc R U . . .
O11 O 0.3335(3) 0.71324(5) 0.2031(3) 0.0392(6) Uani 1 1 d . . . . .
C12 C 0.4384(4) 0.70039(6) 0.1589(4) 0.0348(7) Uani 1 1 d . . . . .
H12 H 0.511524 0.688829 0.245879 0.042 Uiso 1 1 calc R U . . .
C12A C 0.3466(4) 0.68388(7) 0.0130(4) 0.0360(8) Uani 1 1 d . . . . .
O13 O 0.5291(3) 0.72026(5) 0.1414(3) 0.0401(6) Uani 1 1 d . . . . .
O14 O 0.1371(3) 0.71360(5) 0.2637(4) 0.0518(7) Uani 1 1 d . . . . .
C15 C 0.1465(5) 0.71233(9) 0.4047(5) 0.0504(10) Uani 1 1 d . . . . .
O16 O 0.2332(5) 0.69746(11) 0.5036(4) 0.0972(17) Uani 1 1 d . . . . .
C17 C 0.0382(5) 0.73149(8) 0.4200(6) 0.0521(11) Uani 1 1 d . . . . .
H17A H -0.055756 0.734402 0.316956 0.063 Uiso 1 1 calc R U . . .
H17B H 0.094647 0.748244 0.456710 0.063 Uiso 1 1 calc R U . . .
C18 C -0.0164(4) 0.72225(7) 0.5314(6) 0.0476(10) Uani 1 1 d . . . . .
H18A H 0.077229 0.719933 0.635381 0.057 Uiso 1 1 calc R U . . .
H18B H -0.086459 0.735532 0.540086 0.057 Uiso 1 1 calc R U . . .
C19 C -0.1051(5) 0.69711(8) 0.4794(5) 0.0567(12) Uani 1 1 d . . . . .
O20 O -0.1397(7) 0.68699(8) 0.3586(5) 0.1033(18) Uani 1 1 d . . . . .
O21 O -0.1477(4) 0.68753(6) 0.5786(5) 0.0706(11) Uani 1 1 d . . . . .
H21 H -0.178119 0.672117 0.554517 0.106 Uiso 1 1 calc R U . . .
O1B O -0.1764(2) 0.53344(4) 0.0598(3) 0.0293(5) Uani 1 1 d . . . . .
O2B O -0.1483(3) 0.56120(5) 0.0466(3) 0.0318(5) Uani 1 1 d . . . . .
C3B C -0.0599(4) 0.56358(7) -0.0327(4) 0.0311(7) Uani 1 1 d . . . . .
C3MB C -0.0575(5) 0.59243(7) -0.0602(5) 0.0408(8) Uani 1 1 d . . . . .
H3MD H -0.033172 0.601856 0.035270 0.061 Uiso 1 1 calc R U . . .
H3ME H -0.161937 0.597882 -0.143342 0.061 Uiso 1 1 calc R U . . .
H3MF H 0.024306 0.596233 -0.090202 0.061 Uiso 1 1 calc R U . . .
C4B C -0.1297(4) 0.54756(7) -0.1818(4) 0.0328(7) Uani 1 1 d . . . . .
H4BA H -0.116570 0.557365 -0.261489 0.039 Uiso 1 1 calc R U . . .
H4BB H -0.245475 0.545366 -0.220123 0.039 Uiso 1 1 calc R U . . .
C5B C -0.0546(4) 0.52077(7) -0.1640(4) 0.0318(7) Uani 1 1 d . . . . .
H5BA H 0.057697 0.523140 -0.139881 0.038 Uiso 1 1 calc R U . . .
H5BB H -0.110509 0.511726 -0.265124 0.038 Uiso 1 1 calc R U . . .
C5AB C -0.0570(4) 0.50316(6) -0.0398(4) 0.0290(6) Uani 1 1 d . . . . .
H5AB H -0.166960 0.495738 -0.086956 0.035 Uiso 1 1 calc R U . . .
C6B C 0.0561(4) 0.47982(7) -0.0037(4) 0.0324(7) Uani 1 1 d . . . . .
H6B H 0.167038 0.486651 0.038116 0.039 Uiso 1 1 calc R U . . .
C6MB C 0.0159(6) 0.46406(8) -0.1507(5) 0.0461(9) Uani 1 1 d . . . . .
H6MD H -0.098106 0.459905 -0.204539 0.069 Uiso 1 1 calc R U . . .
H6ME H 0.077951 0.447951 -0.121911 0.069 Uiso 1 1 calc R U . . .
H6MF H 0.042141 0.474277 -0.219459 0.069 Uiso 1 1 calc R U . . .
C7B C 0.0521(4) 0.46244(6) 0.1185(4) 0.0319(7) Uani 1 1 d . . . . .
H7BA H 0.130463 0.448238 0.143746 0.038 Uiso 1 1 calc R U . . .
H7BB H -0.054984 0.454547 0.076826 0.038 Uiso 1 1 calc R U . . .
C8B C 0.0904(4) 0.47739(6) 0.2651(4) 0.0309(7) Uani 1 1 d . . . . .
H8BA H 0.199536 0.484571 0.309695 0.037 Uiso 1 1 calc R U . . .
H8BB H 0.087146 0.465442 0.342423 0.037 Uiso 1 1 calc R U . . .
C8AB C -0.0276(4) 0.49949(6) 0.2327(4) 0.0275(6) Uani 1 1 d . . . . .
H8AB H -0.135857 0.491508 0.190416 0.033 Uiso 1 1 calc R U . . .
C9B C 0.0020(4) 0.51503(7) 0.3767(4) 0.0305(6) Uani 1 1 d . . . . .
H9B H -0.089834 0.527151 0.346402 0.037 Uiso 1 1 calc R U . . .
C9MB C 0.0128(5) 0.49775(7) 0.5087(5) 0.0407(8) Uani 1 1 d . . . . .
H9MD H -0.082734 0.486884 0.470031 0.061 Uiso 1 1 calc R U . . .
H9ME H 0.020721 0.508685 0.593648 0.061 Uiso 1 1 calc R U . . .
H9MF H 0.107443 0.486666 0.546520 0.061 Uiso 1 1 calc R U . . .
C10B C 0.1506(4) 0.53117(6) 0.4298(4) 0.0297(6) Uani 1 1 d . . . . .
H10B H 0.245944 0.519770 0.462037 0.036 Uiso 1 1 calc R U . . .
O11B O 0.1362(3) 0.54880(4) 0.3127(3) 0.0295(5) Uani 1 1 d . . . . .
C12B C 0.1129(4) 0.53595(6) 0.1730(4) 0.0263(6) Uani 1 1 d . . . . .
H12B H 0.209467 0.525245 0.198002 0.032 Uiso 1 1 calc R U . . .
C12C C -0.0327(3) 0.51811(6) 0.1067(3) 0.0260(6) Uani 1 1 d . . . . .
O13B O 0.1023(3) 0.55580(4) 0.0707(3) 0.0304(5) Uani 1 1 d . . . . .
O14B O 0.1681(3) 0.54688(5) 0.5568(3) 0.0328(5) Uani 1 1 d . . . . .
C15B C 0.3184(4) 0.55109(6) 0.6730(4) 0.0309(7) Uani 1 1 d . . . . .
O16B O 0.4365(3) 0.54536(5) 0.6683(3) 0.0376(5) Uani 1 1 d . . . . .
C17B C 0.3130(4) 0.56509(7) 0.8055(4) 0.0340(7) Uani 1 1 d . . . . .
H17C H 0.208122 0.562089 0.799791 0.041 Uiso 1 1 calc R U . . .
H17D H 0.324780 0.583972 0.795514 0.041 Uiso 1 1 calc R U . . .
C18B C 0.4447(4) 0.55578(6) 0.9622(4) 0.0327(7) Uani 1 1 d . . . . .
H18C H 0.549659 0.559313 0.969137 0.039 Uiso 1 1 calc R U . . .
H18D H 0.439100 0.565597 1.045967 0.039 Uiso 1 1 calc R U . . .
C19B C 0.4308(4) 0.52725(6) 0.9853(4) 0.0308(7) Uani 1 1 d . . . . .
O20B O 0.3465(3) 0.51276(5) 0.8801(3) 0.0403(6) Uani 1 1 d . . . . .
O21B O 0.5208(3) 0.51997(5) 1.1309(3) 0.0379(5) Uani 1 1 d . . . . .
H21B H 0.503628 0.504253 1.140345 0.057 Uiso 1 1 calc R U . . .
O1D O 0.0570(3) 0.36532(4) 0.7057(3) 0.0299(5) Uani 1 1 d . . . . .
O2D O 0.0517(3) 0.39332(4) 0.6738(3) 0.0314(5) Uani 1 1 d . . . . .
C3D C -0.0189(4) 0.39672(7) 0.5113(4) 0.0321(7) Uani 1 1 d . . . . .
C3MD C -0.0427(4) 0.42556(7) 0.4876(5) 0.0398(8) Uani 1 1 d . . . . .
H3MG H 0.056360 0.434527 0.558180 0.060 Uiso 1 1 calc R U . . .
H3MH H -0.128069 0.431086 0.509236 0.060 Uiso 1 1 calc R U . . .
H3MI H -0.071910 0.429862 0.380101 0.060 Uiso 1 1 calc R U . . .
C4D C -0.1738(4) 0.38100(7) 0.4235(4) 0.0339(7) Uani 1 1 d . . . . .
H4DA H -0.220841 0.378366 0.492815 0.041 Uiso 1 1 calc R U . . .
H4DB H -0.250621 0.391271 0.333244 0.041 Uiso 1 1 calc R U . . .
C5D C -0.1515(4) 0.35442(7) 0.3659(4) 0.0334(7) Uani 1 1 d . . . . .
H5DA H -0.117851 0.357307 0.286377 0.040 Uiso 1 1 calc R U . . .
H5DB H -0.256296 0.345590 0.314298 0.040 Uiso 1 1 calc R U . . .
C5AD C -0.0309(3) 0.33608(6) 0.4899(4) 0.0283(6) Uani 1 1 d . . . . .
H5AD H -0.086913 0.328076 0.543060 0.034 Uiso 1 1 calc R U . . .
C6D C 0.0145(4) 0.31349(6) 0.4154(4) 0.0334(7) Uani 1 1 d . . . . .
H6D H 0.067562 0.320919 0.357923 0.040 Uiso 1 1 calc R U . . .
C6MD C -0.1328(5) 0.29831(8) 0.3002(5) 0.0499(10) Uani 1 1 d . . . . .
H6MG H -0.196061 0.293342 0.350171 0.075 Uiso 1 1 calc R U . . .
H6MH H -0.099165 0.282674 0.266974 0.075 Uiso 1 1 calc R U . . .
H6MI H -0.197414 0.309205 0.209589 0.075 Uiso 1 1 calc R U . . .
C7D C 0.1314(4) 0.29533(6) 0.5401(4) 0.0332(7) Uani 1 1 d . . . . .
H7DA H 0.162910 0.281406 0.490872 0.040 Uiso 1 1 calc R U . . .
H7DB H 0.078748 0.287106 0.594589 0.040 Uiso 1 1 calc R U . . .
C8D C 0.2798(4) 0.30975(6) 0.6574(4) 0.0306(7) Uani 1 1 d . . . . .
H8DA H 0.336178 0.317056 0.604060 0.037 Uiso 1 1 calc R U . . .
H8DB H 0.352683 0.297423 0.737341 0.037 Uiso 1 1 calc R U . . .
C8AD C 0.2368(4) 0.33171(6) 0.7357(4) 0.0279(6) Uani 1 1 d . . . . .
H8AD H 0.184815 0.323523 0.792242 0.034 Uiso 1 1 calc R U . . .
C9D C 0.3832(4) 0.34673(6) 0.8568(4) 0.0295(7) Uani 1 1 d . . . . .
H9D H 0.346039 0.358909 0.911943 0.035 Uiso 1 1 calc R U . . .
C9MD C 0.5103(4) 0.32930(7) 0.9779(4) 0.0429(9) Uani 1 1 d . . . . .
H9MG H 0.562595 0.319368 0.930063 0.064 Uiso 1 1 calc R U . . .
H9MH H 0.460692 0.317318 1.019518 0.064 Uiso 1 1 calc R U . . .
H9MI H 0.589572 0.339968 1.062334 0.064 Uiso 1 1 calc R U . . .
C10D C 0.4486(3) 0.36281(6) 0.7719(4) 0.0297(7) Uani 1 1 d . . . . .
H10D H 0.484573 0.351356 0.712608 0.036 Uiso 1 1 calc R U . . .
O11D O 0.3342(2) 0.38101(4) 0.6710(3) 0.0304(5) Uani 1 1 d . . . . .
C12D C 0.1942(3) 0.36887(6) 0.5509(4) 0.0268(6) Uani 1 1 d . . . . .
H12D H 0.225520 0.358577 0.483621 0.032 Uiso 1 1 calc R U . . .
C12E C 0.1158(3) 0.35047(6) 0.6173(4) 0.0257(6) Uani 1 1 d . . . . .
O13D O 0.0943(2) 0.38905(4) 0.4626(3) 0.0314(5) Uani 1 1 d . . . . .
O14D O 0.5783(2) 0.37786(4) 0.8826(3) 0.0341(5) Uani 1 1 d . . . . .
C15D C 0.6944(4) 0.38404(6) 0.8480(4) 0.0329(7) Uani 1 1 d . . . . .
O16D O 0.6871(3) 0.37980(5) 0.7246(3) 0.0394(6) Uani 1 1 d . . . . .
C17D C 0.8294(4) 0.39780(7) 0.9821(5) 0.0375(8) Uani 1 1 d . . . . .
H17E H 0.824576 0.394117 1.078524 0.045 Uiso 1 1 calc R U . . .
H17F H 0.817702 0.416767 0.963863 0.045 Uiso 1 1 calc R U . . .
C18D C 0.9918(4) 0.38909(7) 1.0021(4) 0.0336(7) Uani 1 1 d . . . . .
H18E H 0.996780 0.392813 0.905773 0.040 Uiso 1 1 calc R U . . .
H18F H 1.077585 0.399059 1.087591 0.040 Uiso 1 1 calc R U . . .
C19D C 1.0184(4) 0.36048(7) 1.0378(4) 0.0318(7) Uani 1 1 d . . . . .
O20D O 0.9114(3) 0.34562(5) 1.0146(3) 0.0424(6) Uani 1 1 d . . . . .
O21D O 1.1697(3) 0.35381(5) 1.0954(3) 0.0383(6) Uani 1 1 d . . . . .
H21D H 1.178970 0.337715 1.110817 0.057 Uiso 1 1 calc R U . . .
N1P N -0.1480(4) 0.63352(7) 0.4823(4) 0.0448(8) Uani 1 1 d . . . . .
C2P C -0.0445(5) 0.62780(11) 0.4324(6) 0.0593(12) Uani 1 1 d . . . . .
H2P H 0.030436 0.640743 0.442114 0.071 Uiso 1 1 calc R U . . .
C3P C -0.0391(6) 0.60427(12) 0.3673(6) 0.0622(13) Uani 1 1 d . . . . .
H3P H 0.036408 0.601349 0.332285 0.075 Uiso 1 1 calc R U . . .
C4P C -0.1433(6) 0.58558(10) 0.3546(5) 0.0582(13) Uani 1 1 d . . . . .
H4P H -0.140190 0.569148 0.312277 0.070 Uiso 1 1 calc R U . . .
C4AP C -0.2577(5) 0.59043(7) 0.4043(4) 0.0421(8) Uani 1 1 d . . . . .
C5P C -0.3749(5) 0.57207(7) 0.3885(5) 0.0471(10) Uani 1 1 d . . . . .
H5P H -0.373210 0.555157 0.350825 0.057 Uiso 1 1 calc R U . . .
C6P C -0.4874(6) 0.57823(9) 0.4257(5) 0.0535(12) Uani 1 1 d . . . . .
H6P H -0.565164 0.565615 0.413001 0.064 Uiso 1 1 calc R U . . .
C6AP C -0.4943(5) 0.60375(9) 0.4854(4) 0.0437(9) Uani 1 1 d . . . . .
C7P C -0.6122(6) 0.61094(12) 0.5205(5) 0.0592(12) Uani 1 1 d . . . . .
H7P H -0.691201 0.598844 0.511195 0.071 Uiso 1 1 calc R U . . .
C8P C -0.6132(5) 0.63595(13) 0.5691(6) 0.0637(14) Uani 1 1 d . . . . .
H8P H -0.694505 0.641449 0.591748 0.076 Uiso 1 1 calc R U . . .
C9P C -0.4923(5) 0.65336(11) 0.5851(5) 0.0574(12) Uani 1 1 d . . . . .
H9P H -0.494762 0.670556 0.618767 0.069 Uiso 1 1 calc R U . . .
N10P N -0.3761(4) 0.64691(7) 0.5556(4) 0.0425(7) Uani 1 1 d . . . . .
C10P C -0.3771(4) 0.62223(7) 0.5061(4) 0.0360(7) Uani 1 1 d . . . . .
C11P C -0.2554(4) 0.61529(7) 0.4664(4) 0.0356(7) Uani 1 1 d . . . . .
N1Q N 0.4872(4) 0.46602(6) 1.1250(4) 0.0369(6) Uani 1 1 d . . . . .
C2Q C 0.4572(6) 0.45560(8) 0.9912(5) 0.0475(10) Uani 1 1 d . . . . .
H2Q H 0.463636 0.466433 0.916180 0.057 Uiso 1 1 calc R U . . .
C3Q C 0.4164(6) 0.42936(8) 0.9529(5) 0.0502(10) Uani 1 1 d . . . . .
H3Q H 0.397069 0.422690 0.855307 0.060 Uiso 1 1 calc R U . . .
C4Q C 0.4051(5) 0.41370(7) 1.0593(5) 0.0435(9) Uani 1 1 d . . . . .
H4Q H 0.377712 0.395913 1.036608 0.052 Uiso 1 1 calc R U . . .
C4AQ C 0.4343(4) 0.42416(6) 1.2028(4) 0.0337(7) Uani 1 1 d . . . . .
C5Q C 0.4170(4) 0.40885(7) 1.3156(4) 0.0359(7) Uani 1 1 d . . . . .
H5Q H 0.390870 0.390964 1.296073 0.043 Uiso 1 1 calc R U . . .
C6Q C 0.4376(4) 0.41957(7) 1.4492(4) 0.0350(7) Uani 1 1 d . . . . .
H6Q H 0.425362 0.409188 1.522656 0.042 Uiso 1 1 calc R U . . .
C6AQ C 0.4778(4) 0.44650(7) 1.4815(4) 0.0328(7) Uani 1 1 d . . . . .
C7Q C 0.4924(4) 0.45883(8) 1.6155(4) 0.0389(8) Uani 1 1 d . . . . .
H7Q H 0.479164 0.449099 1.690575 0.047 Uiso 1 1 calc R U . . .
C8Q C 0.5256(4) 0.48473(8) 1.6378(4) 0.0387(8) Uani 1 1 d . . . . .
H8Q H 0.533151 0.493318 1.726576 0.046 Uiso 1 1 calc R U . . .
C9Q C 0.5484(4) 0.49839(7) 1.5261(4) 0.0362(7) Uani 1 1 d . . . . .
H9Q H 0.573465 0.516341 1.542957 0.043 Uiso 1 1 calc R U . . .
N10Q N 0.5369(3) 0.48763(6) 1.3989(3) 0.0326(6) Uani 1 1 d . . . . .
C10Q C 0.5001(3) 0.46205(6) 1.3756(4) 0.0282(6) Uani 1 1 d . . . . .
C11Q C 0.4756(4) 0.45061(6) 1.2311(4) 0.0295(6) Uani 1 1 d . . . . .
N1R N 1.1700(4) 0.29952(6) 1.1253(4) 0.0422(7) Uani 1 1 d . . . . .
C2R C 1.0402(5) 0.28861(9) 1.0151(5) 0.0574(12) Uani 1 1 d . . . . .
H2R H 0.968774 0.299147 0.930895 0.069 Uiso 1 1 calc R U . . .
C3R C 1.0013(6) 0.26226(10) 1.0148(6) 0.0665(15) Uani 1 1 d . . . . .
H3R H 0.906657 0.255221 0.932327 0.080 Uiso 1 1 calc R U . . .
C4R C 1.1029(5) 0.24707(8) 1.1359(6) 0.0587(12) Uani 1 1 d . . . . .
H4R H 1.078783 0.229301 1.140043 0.070 Uiso 1 1 calc R U . . .
C4AR C 1.2431(4) 0.25793(7) 1.2542(5) 0.0402(8) Uani 1 1 d . . . . .
C5R C 1.3524(5) 0.24290(7) 1.3862(5) 0.0450(9) Uani 1 1 d . . . . .
H5R H 1.333300 0.224919 1.391094 0.054 Uiso 1 1 calc R U . . .
C6R C 1.4809(5) 0.25409(8) 1.5024(5) 0.0447(9) Uani 1 1 d . . . . .
H6R H 1.551593 0.243883 1.588772 0.054 Uiso 1 1 calc R U . . .
C6AR C 1.5138(4) 0.28110(8) 1.4987(4) 0.0360(7) Uani 1 1 d . . . . .
C7R C 1.6455(4) 0.29359(8) 1.6213(4) 0.0424(9) Uani 1 1 d . . . . .
H7R H 1.719463 0.283913 1.708715 0.051 Uiso 1 1 calc R U . . .
C8R C 1.6660(4) 0.31974(8) 1.6135(5) 0.0405(8) Uani 1 1 d . . . . .
H8R H 1.752023 0.328580 1.696249 0.049 Uiso 1 1 calc R U . . .
C9R C 1.5567(4) 0.33316(8) 1.4803(4) 0.0368(8) Uani 1 1 d . . . . .
H9R H 1.573022 0.351227 1.474692 0.044 Uiso 1 1 calc R U . . .
N10R N 1.4329(3) 0.32229(6) 1.3624(3) 0.0328(6) Uani 1 1 d . . . . .
C10R C 1.4109(4) 0.29642(7) 1.3707(4) 0.0310(7) Uani 1 1 d . . . . .
C11R C 1.2711(4) 0.28460(7) 1.2454(4) 0.0344(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 O2 1.472(3) . ?
O1 C12A 1.457(4) . ?
O2 C3 1.406(5) . ?
C3 C3M 1.525(5) . ?
C3 C4 1.520(6) . ?
C3 O13 1.445(5) . ?
C3M H3MA 0.9800 . ?
C3M H3MB 0.9800 . ?
C3M H3MC 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.522(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C5A 1.532(5) . ?
C5A H5AA 1.0000 . ?
C5A C6 1.540(5) . ?
C5A C12A 1.545(5) . ?
C6 H6 1.0000 . ?
C6 C6M 1.541(5) . ?
C6 C7 1.509(5) . ?
C6M H6MA 0.9800 . ?
C6M H6MB 0.9800 . ?
C6M H6MC 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.525(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C8A 1.538(5) . ?
C8A H8AA 1.0000 . ?
C8A C9 1.540(6) . ?
C8A C12A 1.534(5) . ?
C9 H9 1.0000 . ?
C9 C9M 1.528(6) . ?
C9 C10 1.500(6) . ?
C9M H9MA 0.9800 . ?
C9M H9MB 0.9800 . ?
C9M H9MC 0.9800 . ?
C10 H10 1.0000 . ?
C10 O11 1.414(5) . ?
C10 O14 1.438(5) . ?
O11 C12 1.433(4) . ?
C12 H12 1.0000 . ?
C12 C12A 1.530(5) . ?
C12 O13 1.405(4) . ?
O14 C15 1.347(6) . ?
C15 O16 1.202(6) . ?
C15 C17 1.490(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.501(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.497(6) . ?
C19 O20 1.189(7) . ?
C19 O21 1.320(7) . ?
O21 H21 0.8400 . ?
O1B O2B 1.472(3) . ?
O1B C12C 1.455(4) . ?
O2B C3B 1.405(4) . ?
C3B C3MB 1.513(5) . ?
C3B C4B 1.527(5) . ?
C3B O13B 1.444(4) . ?
C3MB H3MD 0.9800 . ?
C3MB H3ME 0.9800 . ?
C3MB H3MF 0.9800 . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.527(5) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C5B C5AB 1.530(5) . ?
C5AB H5AB 1.0000 . ?
C5AB C6B 1.541(5) . ?
C5AB C12C 1.549(4) . ?
C6B H6B 1.0000 . ?
C6B C6MB 1.536(5) . ?
C6B C7B 1.514(5) . ?
C6MB H6MD 0.9800 . ?
C6MB H6ME 0.9800 . ?
C6MB H6MF 0.9800 . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C7B C8B 1.515(5) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C8B C8AB 1.525(4) . ?
C8AB H8AB 1.0000 . ?
C8AB C9B 1.529(5) . ?
C8AB C12C 1.550(4) . ?
C9B H9B 1.0000 . ?
C9B C9MB 1.535(5) . ?
C9B C10B 1.507(5) . ?
C9MB H9MD 0.9800 . ?
C9MB H9ME 0.9800 . ?
C9MB H9MF 0.9800 . ?
C10B H10B 1.0000 . ?
C10B O11B 1.421(4) . ?
C10B O14B 1.429(4) . ?
O11B C12B 1.442(4) . ?
C12B H12B 1.0000 . ?
C12B C12C 1.529(4) . ?
C12B O13B 1.403(4) . ?
O14B C15B 1.356(4) . ?
C15B O16B 1.190(4) . ?
C15B C17B 1.512(5) . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C17B C18B 1.524(5) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C18B C19B 1.503(5) . ?
C19B O20B 1.214(4) . ?
C19B O21B 1.322(4) . ?
O21B H21B 0.8400 . ?
O1D O2D 1.473(3) . ?
O1D C12E 1.460(4) . ?
O2D C3D 1.415(4) . ?
C3D C3MD 1.505(5) . ?
C3D C4D 1.538(4) . ?
C3D O13D 1.435(4) . ?
C3MD H3MG 0.9800 . ?
C3MD H3MH 0.9800 . ?
C3MD H3MI 0.9800 . ?
C4D H4DA 0.9900 . ?
C4D H4DB 0.9900 . ?
C4D C5D 1.536(5) . ?
C5D H5DA 0.9900 . ?
C5D H5DB 0.9900 . ?
C5D C5AD 1.536(4) . ?
C5AD H5AD 1.0000 . ?
C5AD C6D 1.545(5) . ?
C5AD C12E 1.548(4) . ?
C6D H6D 1.0000 . ?
C6D C6MD 1.531(5) . ?
C6D C7D 1.520(4) . ?
C6MD H6MG 0.9800 . ?
C6MD H6MH 0.9800 . ?
C6MD H6MI 0.9800 . ?
C7D H7DA 0.9900 . ?
C7D H7DB 0.9900 . ?
C7D C8D 1.524(4) . ?
C8D H8DA 0.9900 . ?
C8D H8DB 0.9900 . ?
C8D C8AD 1.532(5) . ?
C8AD H8AD 1.0000 . ?
C8AD C9D 1.541(4) . ?
C8AD C12E 1.527(4) . ?
C9D H9D 1.0000 . ?
C9D C9MD 1.520(4) . ?
C9D C10D 1.509(5) . ?
C9MD H9MG 0.9800 . ?
C9MD H9MH 0.9800 . ?
C9MD H9MI 0.9800 . ?
C10D H10D 1.0000 . ?
C10D O11D 1.420(4) . ?
C10D O14D 1.424(4) . ?
O11D C12D 1.435(4) . ?
C12D H12D 1.0000 . ?
C12D C12E 1.536(4) . ?
C12D O13D 1.397(4) . ?
O14D C15D 1.347(4) . ?
C15D O16D 1.202(4) . ?
C15D C17D 1.507(4) . ?
C17D H17E 0.9900 . ?
C17D H17F 0.9900 . ?
C17D C18D 1.536(5) . ?
C18D H18E 0.9900 . ?
C18D H18F 0.9900 . ?
C18D C19D 1.508(5) . ?
C19D O20D 1.209(4) . ?
C19D O21D 1.322(4) . ?
O21D H21D 0.8400 . ?
N1P C2P 1.333(6) . ?
N1P C11P 1.345(5) . ?
C2P H2P 0.9500 . ?
C2P C3P 1.384(8) . ?
C3P H3P 0.9500 . ?
C3P C4P 1.348(8) . ?
C4P H4P 0.9500 . ?
C4P C4AP 1.420(7) . ?
C4AP C5P 1.418(6) . ?
C4AP C11P 1.414(5) . ?
C5P H5P 0.9500 . ?
C5P C6P 1.331(7) . ?
C6P H6P 0.9500 . ?
C6P C6AP 1.454(7) . ?
C6AP C7P 1.379(7) . ?
C6AP C10P 1.410(5) . ?
C7P H7P 0.9500 . ?
C7P C8P 1.377(8) . ?
C8P H8P 0.9500 . ?
C8P C9P 1.411(8) . ?
C9P H9P 0.9500 . ?
C9P N10P 1.320(5) . ?
N10P C10P 1.360(5) . ?
C10P C11P 1.441(5) . ?
N1Q C2Q 1.318(5) . ?
N1Q C11Q 1.357(5) . ?
C2Q H2Q 0.9500 . ?
C2Q C3Q 1.408(6) . ?
C3Q H3Q 0.9500 . ?
C3Q C4Q 1.366(6) . ?
C4Q H4Q 0.9500 . ?
C4Q C4AQ 1.407(5) . ?
C4AQ C5Q 1.434(5) . ?
C4AQ C11Q 1.409(5) . ?
C5Q H5Q 0.9500 . ?
C5Q C6Q 1.349(5) . ?
C6Q H6Q 0.9500 . ?
C6Q C6AQ 1.434(5) . ?
C6AQ C7Q 1.408(5) . ?
C6AQ C10Q 1.409(5) . ?
C7Q H7Q 0.9500 . ?
C7Q C8Q 1.365(6) . ?
C8Q H8Q 0.9500 . ?
C8Q C9Q 1.407(5) . ?
C9Q H9Q 0.9500 . ?
C9Q N10Q 1.324(5) . ?
N10Q C10Q 1.355(4) . ?
C10Q C11Q 1.449(5) . ?
N1R C2R 1.318(5) . ?
N1R C11R 1.350(5) . ?
C2R H2R 0.9500 . ?
C2R C3R 1.408(7) . ?
C3R H3R 0.9500 . ?
C3R C4R 1.364(7) . ?
C4R H4R 0.9500 . ?
C4R C4AR 1.401(5) . ?
C4AR C5R 1.439(6) . ?
C4AR C11R 1.411(5) . ?
C5R H5R 0.9500 . ?
C5R C6R 1.341(6) . ?
C6R H6R 0.9500 . ?
C6R C6AR 1.431(6) . ?
C6AR C7R 1.412(5) . ?
C6AR C10R 1.408(5) . ?
C7R H7R 0.9500 . ?
C7R C8R 1.369(6) . ?
C8R H8R 0.9500 . ?
C8R C9R 1.403(5) . ?
C9R H9R 0.9500 . ?
C9R N10R 1.319(5) . ?
N10R C10R 1.358(5) . ?
C10R C11R 1.446(5) . ?

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
C12A O1 O2 112.2(2) . . ?
C3 O2 O1 108.4(2) . . ?
O2 C3 C3M 103.9(3) . . ?
O2 C3 C4 113.3(4) . . ?
O2 C3 O13 108.5(3) . . ?
C4 C3 C3M 113.8(4) . . ?
O13 C3 C3M 106.8(4) . . ?
O13 C3 C4 110.1(3) . . ?
C3 C3M H3MA 109.5 . . ?
C3 C3M H3MB 109.5 . . ?
C3 C3M H3MC 109.5 . . ?
H3MA C3M H3MB 109.5 . . ?
H3MA C3M H3MC 109.5 . . ?
H3MB C3M H3MC 109.5 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C3 C4 C5 114.2(4) . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C4 C5 H5A 108.3 . . ?
C4 C5 H5B 108.3 . . ?
C4 C5 C5A 116.1(3) . . ?
H5A C5 H5B 107.4 . . ?
C5A C5 H5A 108.3 . . ?
C5A C5 H5B 108.3 . . ?
C5 C5A H5AA 106.3 . . ?
C5 C5A C6 111.7(3) . . ?
C5 C5A C12A 112.2(3) . . ?
C6 C5A H5AA 106.3 . . ?
C6 C5A C12A 113.3(3) . . ?
C12A C5A H5AA 106.3 . . ?
C5A C6 H6 108.4 . . ?
C5A C6 C6M 111.1(3) . . ?
C6M C6 H6 108.4 . . ?
C7 C6 C5A 111.2(3) . . ?
C7 C6 H6 108.4 . . ?
C7 C6 C6M 109.2(3) . . ?
C6 C6M H6MA 109.5 . . ?
C6 C6M H6MB 109.5 . . ?
C6 C6M H6MC 109.5 . . ?
H6MA C6M H6MB 109.5 . . ?
H6MA C6M H6MC 109.5 . . ?
H6MB C6M H6MC 109.5 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C6 C7 C8 111.8(3) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C7 C8 C8A 110.1(3) . . ?
H8A C8 H8B 108.1 . . ?
C8A C8 H8A 109.6 . . ?
C8A C8 H8B 109.6 . . ?
C8 C8A H8AA 107.2 . . ?
C8 C8A C9 112.9(3) . . ?
C9 C8A H8AA 107.2 . . ?
C12A C8A C8 112.0(3) . . ?
C12A C8A H8AA 107.2 . . ?
C12A C8A C9 110.1(3) . . ?
C8A C9 H9 107.7 . . ?
C9M C9 C8A 112.7(3) . . ?
C9M C9 H9 107.7 . . ?
C10 C9 C8A 109.3(3) . . ?
C10 C9 H9 107.7 . . ?
C10 C9 C9M 111.5(4) . . ?
C9 C9M H9MA 109.5 . . ?
C9 C9M H9MB 109.5 . . ?
C9 C9M H9MC 109.5 . . ?
H9MA C9M H9MB 109.5 . . ?
H9MA C9M H9MC 109.5 . . ?
H9MB C9M H9MC 109.5 . . ?
C9 C10 H10 110.9 . . ?
O11 C10 C9 111.5(4) . . ?
O11 C10 H10 110.9 . . ?
O11 C10 O14 102.8(3) . . ?
O14 C10 C9 109.6(3) . . ?
O14 C10 H10 110.9 . . ?
C10 O11 C12 113.8(3) . . ?
O11 C12 H12 108.7 . . ?
O11 C12 C12A 111.8(3) . . ?
C12A C12 H12 108.7 . . ?
O13 C12 O11 105.3(3) . . ?
O13 C12 H12 108.7 . . ?
O13 C12 C12A 113.6(3) . . ?
O1 C12A C5A 106.4(3) . . ?
O1 C12A C8A 103.5(3) . . ?
O1 C12A C12 109.7(3) . . ?
C8A C12A C5A 111.9(3) . . ?
C12 C12A C5A 113.1(3) . . ?
C12 C12A C8A 111.7(3) . . ?
C12 O13 C3 112.9(3) . . ?
C15 O14 C10 119.8(3) . . ?
O14 C15 C17 111.5(4) . . ?
O16 C15 O14 122.8(4) . . ?
O16 C15 C17 125.7(5) . . ?
C15 C17 H17A 109.3 . . ?
C15 C17 H17B 109.3 . . ?
C15 C17 C18 111.5(4) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 C17 111.4(4) . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
O20 C19 C18 124.1(5) . . ?
O20 C19 O21 122.5(5) . . ?
O21 C19 C18 113.4(4) . . ?
C19 O21 H21 109.5 . . ?
C12C O1B O2B 111.7(2) . . ?
C3B O2B O1B 108.5(2) . . ?
O2B C3B C3MB 104.5(3) . . ?
O2B C3B C4B 112.5(3) . . ?
O2B C3B O13B 108.4(3) . . ?
C3MB C3B C4B 113.4(3) . . ?
O13B C3B C3MB 107.1(3) . . ?
O13B C3B C4B 110.6(3) . . ?
C3B C3MB H3MD 109.5 . . ?
C3B C3MB H3ME 109.5 . . ?
C3B C3MB H3MF 109.5 . . ?
H3MD C3MB H3ME 109.5 . . ?
H3MD C3MB H3MF 109.5 . . ?
H3ME C3MB H3MF 109.5 . . ?
C3B C4B H4BA 108.6 . . ?
C3B C4B H4BB 108.6 . . ?
C3B C4B C5B 114.5(3) . . ?
H4BA C4B H4BB 107.6 . . ?
C5B C4B H4BA 108.6 . . ?
C5B C4B H4BB 108.6 . . ?
C4B C5B H5BA 108.3 . . ?
C4B C5B H5BB 108.3 . . ?
C4B C5B C5AB 116.1(3) . . ?
H5BA C5B H5BB 107.4 . . ?
C5AB C5B H5BA 108.3 . . ?
C5AB C5B H5BB 108.3 . . ?
C5B C5AB H5AB 105.9 . . ?
C5B C5AB C6B 111.6(3) . . ?
C5B C5AB C12C 113.2(3) . . ?
C6B C5AB H5AB 105.9 . . ?
C6B C5AB C12C 113.6(3) . . ?
C12C C5AB H5AB 105.9 . . ?
C5AB C6B H6B 108.0 . . ?
C6MB C6B C5AB 111.4(3) . . ?
C6MB C6B H6B 108.0 . . ?
C7B C6B C5AB 111.2(3) . . ?
C7B C6B H6B 108.0 . . ?
C7B C6B C6MB 110.1(3) . . ?
C6B C6MB H6MD 109.5 . . ?
C6B C6MB H6ME 109.5 . . ?
C6B C6MB H6MF 109.5 . . ?
H6MD C6MB H6ME 109.5 . . ?
H6MD C6MB H6MF 109.5 . . ?
H6ME C6MB H6MF 109.5 . . ?
C6B C7B H7BA 109.3 . . ?
C6B C7B H7BB 109.3 . . ?
C6B C7B C8B 111.6(3) . . ?
H7BA C7B H7BB 108.0 . . ?
C8B C7B H7BA 109.3 . . ?
C8B C7B H7BB 109.3 . . ?
C7B C8B H8BA 109.3 . . ?
C7B C8B H8BB 109.3 . . ?
C7B C8B C8AB 111.4(3) . . ?
H8BA C8B H8BB 108.0 . . ?
C8AB C8B H8BA 109.3 . . ?
C8AB C8B H8BB 109.3 . . ?
C8B C8AB H8AB 107.1 . . ?
C8B C8AB C9B 114.1(3) . . ?
C8B C8AB C12C 111.4(3) . . ?
C9B C8AB H8AB 107.1 . . ?
C9B C8AB C12C 109.6(3) . . ?
C12C C8AB H8AB 107.1 . . ?
C8AB C9B H9B 107.8 . . ?
C8AB C9B C9MB 112.7(3) . . ?
C9MB C9B H9B 107.8 . . ?
C10B C9B C8AB 109.5(3) . . ?
C10B C9B H9B 107.8 . . ?
C10B C9B C9MB 111.0(3) . . ?
C9B C9MB H9MD 109.5 . . ?
C9B C9MB H9ME 109.5 . . ?
C9B C9MB H9MF 109.5 . . ?
H9MD C9MB H9ME 109.5 . . ?
H9MD C9MB H9MF 109.5 . . ?
H9ME C9MB H9MF 109.5 . . ?
C9B C10B H10B 110.5 . . ?
O11B C10B C9B 111.4(2) . . ?
O11B C10B H10B 110.5 . . ?
O11B C10B O14B 105.7(3) . . ?
O14B C10B C9B 108.0(3) . . ?
O14B C10B H10B 110.5 . . ?
C10B O11B C12B 112.8(2) . . ?
O11B C12B H12B 108.6 . . ?
O11B C12B C12C 111.9(2) . . ?
C12C C12B H12B 108.6 . . ?
O13B C12B O11B 105.8(2) . . ?
O13B C12B H12B 108.6 . . ?
O13B C12B C12C 113.3(2) . . ?
O1B C12C C5AB 106.2(2) . . ?
O1B C12C C8AB 104.5(2) . . ?
O1B C12C C12B 109.7(2) . . ?
C5AB C12C C8AB 111.6(3) . . ?
C12B C12C C5AB 113.2(3) . . ?
C12B C12C C8AB 111.1(2) . . ?
C12B O13B C3B 112.9(2) . . ?
C15B O14B C10B 117.2(3) . . ?
O14B C15B C17B 109.8(3) . . ?
O16B C15B O14B 124.8(3) . . ?
O16B C15B C17B 125.3(3) . . ?
C15B C17B H17C 109.3 . . ?
C15B C17B H17D 109.3 . . ?
C15B C17B C18B 111.5(3) . . ?
H17C C17B H17D 108.0 . . ?
C18B C17B H17C 109.3 . . ?
C18B C17B H17D 109.3 . . ?
C17B C18B H18C 109.3 . . ?
C17B C18B H18D 109.3 . . ?
H18C C18B H18D 107.9 . . ?
C19B C18B C17B 111.7(3) . . ?
C19B C18B H18C 109.3 . . ?
C19B C18B H18D 109.3 . . ?
O20B C19B C18B 123.0(3) . . ?
O20B C19B O21B 124.5(3) . . ?
O21B C19B C18B 112.5(3) . . ?
C19B O21B H21B 109.5 . . ?
C12E O1D O2D 111.7(2) . . ?
C3D O2D O1D 108.1(2) . . ?
O2D C3D C3MD 104.5(3) . . ?
O2D C3D C4D 112.1(3) . . ?
O2D C3D O13D 108.4(2) . . ?
C3MD C3D C4D 113.6(3) . . ?
O13D C3D C3MD 107.6(3) . . ?
O13D C3D C4D 110.3(3) . . ?
C3D C3MD H3MG 109.5 . . ?
C3D C3MD H3MH 109.5 . . ?
C3D C3MD H3MI 109.5 . . ?
H3MG C3MD H3MH 109.5 . . ?
H3MG C3MD H3MI 109.5 . . ?
H3MH C3MD H3MI 109.5 . . ?
C3D C4D H4DA 108.7 . . ?
C3D C4D H4DB 108.7 . . ?
H4DA C4D H4DB 107.6 . . ?
C5D C4D C3D 114.1(3) . . ?
C5D C4D H4DA 108.7 . . ?
C5D C4D H4DB 108.7 . . ?
C4D C5D H5DA 108.2 . . ?
C4D C5D H5DB 108.2 . . ?
C4D C5D C5AD 116.2(3) . . ?
H5DA C5D H5DB 107.4 . . ?
C5AD C5D H5DA 108.2 . . ?
C5AD C5D H5DB 108.2 . . ?
C5D C5AD H5AD 106.3 . . ?
C5D C5AD C6D 111.3(3) . . ?
C5D C5AD C12E 113.0(3) . . ?
C6D C5AD H5AD 106.3 . . ?
C6D C5AD C12E 113.1(2) . . ?
C12E C5AD H5AD 106.3 . . ?
C5AD C6D H6D 108.3 . . ?
C6MD C6D C5AD 111.5(3) . . ?
C6MD C6D H6D 108.3 . . ?
C7D C6D C5AD 110.3(3) . . ?
C7D C6D H6D 108.3 . . ?
C7D C6D C6MD 109.9(3) . . ?
C6D C6MD H6MG 109.5 . . ?
C6D C6MD H6MH 109.5 . . ?
C6D C6MD H6MI 109.5 . . ?
H6MG C6MD H6MH 109.5 . . ?
H6MG C6MD H6MI 109.5 . . ?
H6MH C6MD H6MI 109.5 . . ?
C6D C7D H7DA 109.3 . . ?
C6D C7D H7DB 109.3 . . ?
C6D C7D C8D 111.5(3) . . ?
H7DA C7D H7DB 108.0 . . ?
C8D C7D H7DA 109.3 . . ?
C8D C7D H7DB 109.3 . . ?
C7D C8D H8DA 109.4 . . ?
C7D C8D H8DB 109.4 . . ?
C7D C8D C8AD 111.2(3) . . ?
H8DA C8D H8DB 108.0 . . ?
C8AD C8D H8DA 109.4 . . ?
C8AD C8D H8DB 109.4 . . ?
C8D C8AD H8AD 107.1 . . ?
C8D C8AD C9D 113.2(3) . . ?
C9D C8AD H8AD 107.1 . . ?
C12E C8AD C8D 111.9(3) . . ?
C12E C8AD H8AD 107.1 . . ?
C12E C8AD C9D 110.2(2) . . ?
C8AD C9D H9D 107.8 . . ?
C9MD C9D C8AD 113.3(3) . . ?
C9MD C9D H9D 107.8 . . ?
C10D C9D C8AD 108.3(3) . . ?
C10D C9D H9D 107.8 . . ?
C10D C9D C9MD 111.7(3) . . ?
C9D C9MD H9MG 109.5 . . ?
C9D C9MD H9MH 109.5 . . ?
C9D C9MD H9MI 109.5 . . ?
H9MG C9MD H9MH 109.5 . . ?
H9MG C9MD H9MI 109.5 . . ?
H9MH C9MD H9MI 109.5 . . ?
C9D C10D H10D 110.4 . . ?
O11D C10D C9D 111.3(2) . . ?
O11D C10D H10D 110.4 . . ?
O11D C10D O14D 105.7(2) . . ?
O14D C10D C9D 108.5(3) . . ?
O14D C10D H10D 110.4 . . ?
C10D O11D C12D 112.8(2) . . ?
O11D C12D H12D 108.5 . . ?
O11D C12D C12E 111.9(3) . . ?
C12E C12D H12D 108.5 . . ?
O13D C12D O11D 106.0(2) . . ?
O13D C12D H12D 108.5 . . ?
O13D C12D C12E 113.3(2) . . ?
O1D C12E C5AD 105.8(2) . . ?
O1D C12E C8AD 104.2(3) . . ?
O1D C12E C12D 109.7(2) . . ?
C8AD C12E C5AD 111.9(2) . . ?
C8AD C12E C12D 111.6(2) . . ?
C12D C12E C5AD 113.0(3) . . ?
C12D O13D C3D 113.5(2) . . ?
C15D O14D C10D 117.2(3) . . ?
O14D C15D C17D 110.8(3) . . ?
O16D C15D O14D 123.9(3) . . ?
O16D C15D C17D 125.3(3) . . ?
C15D C17D H17E 109.4 . . ?
C15D C17D H17F 109.4 . . ?
C15D C17D C18D 111.3(3) . . ?
H17E C17D H17F 108.0 . . ?
C18D C17D H17E 109.4 . . ?
C18D C17D H17F 109.4 . . ?
C17D C18D H18E 109.4 . . ?
C17D C18D H18F 109.4 . . ?
H18E C18D H18F 108.0 . . ?
C19D C18D C17D 111.3(3) . . ?
C19D C18D H18E 109.4 . . ?
C19D C18D H18F 109.4 . . ?
O20D C19D C18D 122.8(3) . . ?
O20D C19D O21D 124.7(3) . . ?
O21D C19D C18D 112.4(3) . . ?
C19D O21D H21D 109.5 . . ?
C2P N1P C11P 117.6(4) . . ?
N1P C2P H2P 117.8 . . ?
N1P C2P C3P 124.3(5) . . ?
C3P C2P H2P 117.8 . . ?
C2P C3P H3P 120.7 . . ?
C4P C3P C2P 118.6(4) . . ?
C4P C3P H3P 120.7 . . ?
C3P C4P H4P 120.0 . . ?
C3P C4P C4AP 120.1(4) . . ?
C4AP C4P H4P 120.0 . . ?
C5P C4AP C4P 123.0(4) . . ?
C11P C4AP C4P 116.9(4) . . ?
C11P C4AP C5P 120.0(4) . . ?
C4AP C5P H5P 119.6 . . ?
C6P C5P C4AP 120.8(4) . . ?
C6P C5P H5P 119.6 . . ?
C5P C6P H6P 119.1 . . ?
C5P C6P C6AP 121.8(4) . . ?
C6AP C6P H6P 119.1 . . ?
C7P C6AP C6P 123.0(4) . . ?
C7P C6AP C10P 118.2(4) . . ?
C10P C6AP C6P 118.8(4) . . ?
C6AP C7P H7P 120.6 . . ?
C8P C7P C6AP 118.8(5) . . ?
C8P C7P H7P 120.6 . . ?
C7P C8P H8P 120.3 . . ?
C7P C8P C9P 119.4(4) . . ?
C9P C8P H8P 120.3 . . ?
C8P C9P H9P 118.4 . . ?
N10P C9P C8P 123.2(5) . . ?
N10P C9P H9P 118.4 . . ?
C9P N10P C10P 116.9(4) . . ?
C6AP C10P C11P 119.0(3) . . ?
N10P C10P C6AP 123.5(4) . . ?
N10P C10P C11P 117.5(3) . . ?
N1P C11P C4AP 122.4(4) . . ?
N1P C11P C10P 117.8(3) . . ?
C4AP C11P C10P 119.7(3) . . ?
C2Q N1Q C11Q 118.0(3) . . ?
N1Q C2Q H2Q 118.1 . . ?
N1Q C2Q C3Q 123.8(4) . . ?
C3Q C2Q H2Q 118.1 . . ?
C2Q C3Q H3Q 120.8 . . ?
C4Q C3Q C2Q 118.5(4) . . ?
C4Q C3Q H3Q 120.8 . . ?
C3Q C4Q H4Q 120.3 . . ?
C3Q C4Q C4AQ 119.4(4) . . ?
C4AQ C4Q H4Q 120.3 . . ?
C4Q C4AQ C5Q 121.6(3) . . ?
C4Q C4AQ C11Q 118.0(3) . . ?
C11Q C4AQ C5Q 120.4(3) . . ?
C4AQ C5Q H5Q 119.7 . . ?
C6Q C5Q C4AQ 120.7(3) . . ?
C6Q C5Q H5Q 119.7 . . ?
C5Q C6Q H6Q 119.7 . . ?
C5Q C6Q C6AQ 120.6(3) . . ?
C6AQ C6Q H6Q 119.7 . . ?
C7Q C6AQ C6Q 122.6(3) . . ?
C7Q C6AQ C10Q 116.9(3) . . ?
C10Q C6AQ C6Q 120.5(3) . . ?
C6AQ C7Q H7Q 119.9 . . ?
C8Q C7Q C6AQ 120.2(3) . . ?
C8Q C7Q H7Q 119.9 . . ?
C7Q C8Q H8Q 120.8 . . ?
C7Q C8Q C9Q 118.4(3) . . ?
C9Q C8Q H8Q 120.8 . . ?
C8Q C9Q H9Q 118.2 . . ?
N10Q C9Q C8Q 123.7(4) . . ?
N10Q C9Q H9Q 118.2 . . ?
C9Q N10Q C10Q 117.6(3) . . ?
C6AQ C10Q C11Q 118.8(3) . . ?
N10Q C10Q C6AQ 123.3(3) . . ?
N10Q C10Q C11Q 117.8(3) . . ?
N1Q C11Q C4AQ 122.2(3) . . ?
N1Q C11Q C10Q 118.8(3) . . ?
C4AQ C11Q C10Q 118.9(3) . . ?
C2R N1R C11R 118.2(4) . . ?
N1R C2R H2R 118.1 . . ?
N1R C2R C3R 123.8(4) . . ?
C3R C2R H2R 118.1 . . ?
C2R C3R H3R 120.8 . . ?
C4R C3R C2R 118.4(4) . . ?
C4R C3R H3R 120.8 . . ?
C3R C4R H4R 120.3 . . ?
C3R C4R C4AR 119.4(4) . . ?
C4AR C4R H4R 120.3 . . ?
C4R C4AR C5R 121.6(4) . . ?
C4R C4AR C11R 118.2(4) . . ?
C11R C4AR C5R 120.1(3) . . ?
C4AR C5R H5R 119.8 . . ?
C6R C5R C4AR 120.5(4) . . ?
C6R C5R H5R 119.8 . . ?
C5R C6R H6R 119.3 . . ?
C5R C6R C6AR 121.3(4) . . ?
C6AR C6R H6R 119.3 . . ?
C7R C6AR C6R 122.6(3) . . ?
C10R C6AR C6R 120.0(3) . . ?
C10R C6AR C7R 117.4(3) . . ?
C6AR C7R H7R 120.2 . . ?
C8R C7R C6AR 119.6(3) . . ?
C8R C7R H7R 120.2 . . ?
C7R C8R H8R 120.8 . . ?
C7R C8R C9R 118.4(3) . . ?
C9R C8R H8R 120.8 . . ?
C8R C9R H9R 117.9 . . ?
N10R C9R C8R 124.2(4) . . ?
N10R C9R H9R 117.9 . . ?
C9R N10R C10R 117.6(3) . . ?
C6AR C10R C11R 119.2(3) . . ?
N10R C10R C6AR 122.8(3) . . ?
N10R C10R C11R 117.9(3) . . ?
N1R C11R C4AR 122.0(3) . . ?
N1R C11R C10R 119.0(3) . . ?
C4AR C11R C10R 118.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 O2 C3 C3M 172.9(3) . . . . ?
O1 O2 C3 C4 48.9(4) . . . . ?
O1 O2 C3 O13 -73.7(4) . . . . ?
O2 O1 C12A C5A -106.0(3) . . . . ?
O2 O1 C12A C8A 136.0(3) . . . . ?
O2 O1 C12A C12 16.7(4) . . . . ?
O2 C3 C4 C5 -95.1(4) . . . . ?
O2 C3 O13 C12 34.7(4) . . . . ?
C3 C4 C5 C5A 57.5(5) . . . . ?
C3M C3 C4 C5 146.5(4) . . . . ?
C3M C3 O13 C12 146.2(3) . . . . ?
C4 C3 O13 C12 -89.8(4) . . . . ?
C4 C5 C5A C6 -167.6(3) . . . . ?
C4 C5 C5A C12A -39.1(5) . . . . ?
C5 C5A C6 C6M -59.0(4) . . . . ?
C5 C5A C6 C7 179.1(3) . . . . ?
C5 C5A C12A O1 71.2(3) . . . . ?
C5 C5A C12A C8A -176.4(3) . . . . ?
C5 C5A C12A C12 -49.3(4) . . . . ?
C5A C6 C7 C8 -56.4(4) . . . . ?
C6 C5A C12A O1 -161.1(3) . . . . ?
C6 C5A C12A C8A -48.7(4) . . . . ?
C6 C5A C12A C12 78.4(4) . . . . ?
C6 C7 C8 C8A 59.2(4) . . . . ?
C6M C6 C7 C8 -179.4(3) . . . . ?
C7 C8 C8A C9 178.8(3) . . . . ?
C7 C8 C8A C12A -56.3(4) . . . . ?
C8 C8A C9 C9M -52.3(5) . . . . ?
C8 C8A C9 C10 72.3(4) . . . . ?
C8 C8A C12A O1 165.4(3) . . . . ?
C8 C8A C12A C5A 51.3(4) . . . . ?
C8 C8A C12A C12 -76.7(4) . . . . ?
C8A C9 C10 O11 59.0(4) . . . . ?
C8A C9 C10 O14 172.2(3) . . . . ?
C9 C8A C12A O1 -68.1(4) . . . . ?
C9 C8A C12A C5A 177.7(3) . . . . ?
C9 C8A C12A C12 49.8(4) . . . . ?
C9 C10 O11 C12 -61.1(4) . . . . ?
C9 C10 O14 C15 125.1(4) . . . . ?
C9M C9 C10 O11 -175.7(3) . . . . ?
C9M C9 C10 O14 -62.6(4) . . . . ?
C10 O11 C12 C12A 55.8(4) . . . . ?
C10 O11 C12 O13 179.6(3) . . . . ?
C10 O14 C15 O16 1.7(7) . . . . ?
C10 O14 C15 C17 -178.7(3) . . . . ?
O11 C10 O14 C15 -116.2(4) . . . . ?
O11 C12 C12A O1 64.1(4) . . . . ?
O11 C12 C12A C5A -177.3(3) . . . . ?
O11 C12 C12A C8A -50.0(4) . . . . ?
O11 C12 O13 C3 -94.8(3) . . . . ?
C12A O1 O2 C3 44.0(4) . . . . ?
C12A C5A C6 C6M 173.0(3) . . . . ?
C12A C5A C6 C7 51.1(4) . . . . ?
C12A C8A C9 C9M -178.2(4) . . . . ?
C12A C8A C9 C10 -53.6(4) . . . . ?
C12A C12 O13 C3 27.9(4) . . . . ?
O13 C3 C4 C5 26.6(5) . . . . ?
O13 C12 C12A O1 -54.9(4) . . . . ?
O13 C12 C12A C5A 63.7(4) . . . . ?
O13 C12 C12A C8A -169.0(3) . . . . ?
O14 C10 O11 C12 -178.5(3) . . . . ?
O14 C15 C17 C18 151.2(4) . . . . ?
C15 C17 C18 C19 -60.0(5) . . . . ?
O16 C15 C17 C18 -29.2(7) . . . . ?
C17 C18 C19 O20 -6.1(7) . . . . ?
C17 C18 C19 O21 176.4(4) . . . . ?
O1B O2B C3B C3MB 172.3(2) . . . . ?
O1B O2B C3B C4B 48.8(3) . . . . ?
O1B O2B C3B O13B -73.7(3) . . . . ?
O2B O1B C12C C5AB -106.3(3) . . . . ?
O2B O1B C12C C8AB 135.6(2) . . . . ?
O2B O1B C12C C12B 16.4(3) . . . . ?
O2B C3B C4B C5B -95.1(3) . . . . ?
O2B C3B O13B C12B 33.5(3) . . . . ?
C3B C4B C5B C5AB 55.8(4) . . . . ?
C3MB C3B C4B C5B 146.6(3) . . . . ?
C3MB C3B O13B C12B 145.7(3) . . . . ?
C4B C3B O13B C12B -90.2(3) . . . . ?
C4B C5B C5AB C6B -165.9(3) . . . . ?
C4B C5B C5AB C12C -36.3(4) . . . . ?
C5B C5AB C6B C6MB -56.4(4) . . . . ?
C5B C5AB C6B C7B -179.7(3) . . . . ?
C5B C5AB C12C O1B 69.4(3) . . . . ?
C5B C5AB C12C C8AB -177.2(2) . . . . ?
C5B C5AB C12C C12B -51.0(3) . . . . ?
C5AB C6B C7B C8B -55.6(4) . . . . ?
C6B C5AB C12C O1B -162.0(3) . . . . ?
C6B C5AB C12C C8AB -48.6(3) . . . . ?
C6B C5AB C12C C12B 77.6(3) . . . . ?
C6B C7B C8B C8AB 59.3(4) . . . . ?
C6MB C6B C7B C8B -179.7(3) . . . . ?
C7B C8B C8AB C9B 178.7(3) . . . . ?
C7B C8B C8AB C12C -56.5(3) . . . . ?
C8B C8AB C9B C9MB -52.8(4) . . . . ?
C8B C8AB C9B C10B 71.2(3) . . . . ?
C8B C8AB C12C O1B 165.2(2) . . . . ?
C8B C8AB C12C C5AB 50.8(3) . . . . ?
C8B C8AB C12C C12B -76.5(3) . . . . ?
C8AB C9B C10B O11B 60.0(3) . . . . ?
C8AB C9B C10B O14B 175.7(2) . . . . ?
C9B C8AB C12C O1B -67.5(3) . . . . ?
C9B C8AB C12C C5AB 178.1(2) . . . . ?
C9B C8AB C12C C12B 50.8(3) . . . . ?
C9B C10B O11B C12B -61.3(3) . . . . ?
C9B C10B O14B C15B 143.5(3) . . . . ?
C9MB C9B C10B O11B -175.0(3) . . . . ?
C9MB C9B C10B O14B -59.3(3) . . . . ?
C10B O11B C12B C12C 56.6(3) . . . . ?
C10B O11B C12B O13B -179.6(2) . . . . ?
C10B O14B C15B O16B 9.5(5) . . . . ?
C10B O14B C15B C17B -172.9(3) . . . . ?
O11B C10B O14B C15B -97.1(3) . . . . ?
O11B C12B C12C O1B 63.9(3) . . . . ?
O11B C12B C12C C5AB -177.7(2) . . . . ?
O11B C12B C12C C8AB -51.2(3) . . . . ?
O11B C12B O13B C3B -93.8(3) . . . . ?
C12C O1B O2B C3B 44.9(3) . . . . ?
C12C C5AB C6B C6MB 174.2(3) . . . . ?
C12C C5AB C6B C7B 50.9(4) . . . . ?
C12C C8AB C9B C9MB -178.6(3) . . . . ?
C12C C8AB C9B C10B -54.5(3) . . . . ?
C12C C12B O13B C3B 29.2(4) . . . . ?
O13B C3B C4B C5B 26.2(4) . . . . ?
O13B C12B C12C O1B -55.6(3) . . . . ?
O13B C12B C12C C5AB 62.8(3) . . . . ?
O13B C12B C12C C8AB -170.7(2) . . . . ?
O14B C10B O11B C12B -178.4(2) . . . . ?
O14B C15B C17B C18B 143.4(3) . . . . ?
C15B C17B C18B C19B -60.2(4) . . . . ?
O16B C15B C17B C18B -39.0(5) . . . . ?
C17B C18B C19B O20B 14.3(5) . . . . ?
C17B C18B C19B O21B -166.2(3) . . . . ?
O1D O2D C3D C3MD 171.5(2) . . . . ?
O1D O2D C3D C4D 48.1(3) . . . . ?
O1D O2D C3D O13D -73.9(3) . . . . ?
O2D O1D C12E C5AD -107.7(2) . . . . ?
O2D O1D C12E C8AD 134.2(2) . . . . ?
O2D O1D C12E C12D 14.5(3) . . . . ?
O2D C3D C4D C5D -95.2(4) . . . . ?
O2D C3D O13D C12D 32.7(3) . . . . ?
C3D C4D C5D C5AD 56.2(4) . . . . ?
C3MD C3D C4D C5D 146.6(3) . . . . ?
C3MD C3D O13D C12D 145.3(3) . . . . ?
C4D C3D O13D C12D -90.3(3) . . . . ?
C4D C5D C5AD C6D -164.9(3) . . . . ?
C4D C5D C5AD C12E -36.5(4) . . . . ?
C5D C5AD C6D C6MD -56.5(4) . . . . ?
C5D C5AD C6D C7D -178.9(3) . . . . ?
C5D C5AD C12E O1D 69.2(3) . . . . ?
C5D C5AD C12E C8AD -177.9(3) . . . . ?
C5D C5AD C12E C12D -50.8(4) . . . . ?
C5AD C6D C7D C8D -56.5(4) . . . . ?
C6D C5AD C12E O1D -163.3(3) . . . . ?
C6D C5AD C12E C8AD -50.4(4) . . . . ?
C6D C5AD C12E C12D 76.7(3) . . . . ?
C6D C7D C8D C8AD 58.5(4) . . . . ?
C6MD C6D C7D C8D -179.9(3) . . . . ?
C7D C8D C8AD C9D 179.4(3) . . . . ?
C7D C8D C8AD C12E -55.4(4) . . . . ?
C8D C8AD C9D C9MD -53.1(4) . . . . ?
C8D C8AD C9D C10D 71.3(3) . . . . ?
C8D C8AD C12E O1D 165.0(2) . . . . ?
C8D C8AD C12E C5AD 51.1(4) . . . . ?
C8D C8AD C12E C12D -76.7(3) . . . . ?
C8AD C9D C10D O11D 60.9(3) . . . . ?
C8AD C9D C10D O14D 176.7(2) . . . . ?
C9D C8AD C12E O1D -68.1(3) . . . . ?
C9D C8AD C12E C5AD 178.0(3) . . . . ?
C9D C8AD C12E C12D 50.3(4) . . . . ?
C9D C10D O11D C12D -62.5(3) . . . . ?
C9D C10D O14D C15D 150.8(3) . . . . ?
C9MD C9D C10D O11D -173.7(3) . . . . ?
C9MD C9D C10D O14D -57.8(3) . . . . ?
C10D O11D C12D C12E 55.9(3) . . . . ?
C10D O11D C12D O13D 179.9(3) . . . . ?
C10D O14D C15D O16D 7.4(4) . . . . ?
C10D O14D C15D C17D -174.9(3) . . . . ?
O11D C10D O14D C15D -89.7(3) . . . . ?
O11D C12D C12E O1D 65.0(3) . . . . ?
O11D C12D C12E C5AD -177.2(2) . . . . ?
O11D C12D C12E C8AD -50.0(3) . . . . ?
O11D C12D O13D C3D -93.4(3) . . . . ?
C12E O1D O2D C3D 46.2(3) . . . . ?
C12E C5AD C6D C6MD 175.2(3) . . . . ?
C12E C5AD C6D C7D 52.7(4) . . . . ?
C12E C8AD C9D C9MD -179.3(3) . . . . ?
C12E C8AD C9D C10D -54.8(3) . . . . ?
C12E C12D O13D C3D 29.7(4) . . . . ?
O13D C3D C4D C5D 25.7(4) . . . . ?
O13D C12D C12E O1D -54.8(3) . . . . ?
O13D C12D C12E C5AD 63.0(4) . . . . ?
O13D C12D C12E C8AD -169.8(3) . . . . ?
O14D C10D O11D C12D 179.9(3) . . . . ?
O14D C15D C17D C18D 140.8(3) . . . . ?
C15D C17D C18D C19D -61.8(4) . . . . ?
O16D C15D C17D C18D -41.5(5) . . . . ?
C17D C18D C19D O20D 17.2(5) . . . . ?
C17D C18D C19D O21D -163.2(3) . . . . ?
N1P C2P C3P C4P -0.9(8) . . . . ?
C2P N1P C11P C4AP 2.2(6) . . . . ?
C2P N1P C11P C10P -174.1(4) . . . . ?
C2P C3P C4P C4AP 1.4(7) . . . . ?
C3P C4P C4AP C5P 177.3(4) . . . . ?
C3P C4P C4AP C11P -0.1(6) . . . . ?
C4P C4AP C5P C6P -174.7(4) . . . . ?
C4P C4AP C11P N1P -1.8(5) . . . . ?
C4P C4AP C11P C10P 174.5(3) . . . . ?
C4AP C5P C6P C6AP -0.6(6) . . . . ?
C5P C4AP C11P N1P -179.3(3) . . . . ?
C5P C4AP C11P C10P -3.0(5) . . . . ?
C5P C6P C6AP C7P 178.0(4) . . . . ?
C5P C6P C6AP C10P -0.9(6) . . . . ?
C6P C6AP C7P C8P -176.8(4) . . . . ?
C6P C6AP C10P N10P 177.5(4) . . . . ?
C6P C6AP C10P C11P 0.5(5) . . . . ?
C6AP C7P C8P C9P -1.4(7) . . . . ?
C6AP C10P C11P N1P 177.9(3) . . . . ?
C6AP C10P C11P C4AP 1.5(5) . . . . ?
C7P C6AP C10P N10P -1.4(6) . . . . ?
C7P C6AP C10P C11P -178.5(4) . . . . ?
C7P C8P C9P N10P 0.0(7) . . . . ?
C8P C9P N10P C10P 0.7(6) . . . . ?
C9P N10P C10P C6AP 0.0(6) . . . . ?
C9P N10P C10P C11P 177.1(4) . . . . ?
N10P C10P C11P N1P 0.7(5) . . . . ?
N10P C10P C11P C4AP -175.8(3) . . . . ?
C10P C6AP C7P C8P 2.0(6) . . . . ?
C11P N1P C2P C3P -0.9(7) . . . . ?
C11P C4AP C5P C6P 2.6(6) . . . . ?
N1Q C2Q C3Q C4Q 0.8(7) . . . . ?
C2Q N1Q C11Q C4AQ 0.5(5) . . . . ?
C2Q N1Q C11Q C10Q -176.9(3) . . . . ?
C2Q C3Q C4Q C4AQ 0.0(7) . . . . ?
C3Q C4Q C4AQ C5Q 177.2(4) . . . . ?
C3Q C4Q C4AQ C11Q -0.5(6) . . . . ?
C4Q C4AQ C5Q C6Q -176.6(3) . . . . ?
C4Q C4AQ C11Q N1Q 0.2(5) . . . . ?
C4Q C4AQ C11Q C10Q 177.6(3) . . . . ?
C4AQ C5Q C6Q C6AQ -0.3(5) . . . . ?
C5Q C4AQ C11Q N1Q -177.5(3) . . . . ?
C5Q C4AQ C11Q C10Q -0.1(5) . . . . ?
C5Q C6Q C6AQ C7Q 176.7(3) . . . . ?
C5Q C6Q C6AQ C10Q -1.5(5) . . . . ?
C6Q C6AQ C7Q C8Q -177.8(3) . . . . ?
C6Q C6AQ C10Q N10Q 179.5(3) . . . . ?
C6Q C6AQ C10Q C11Q 2.4(4) . . . . ?
C6AQ C7Q C8Q C9Q -1.6(5) . . . . ?
C6AQ C10Q C11Q N1Q 175.9(3) . . . . ?
C6AQ C10Q C11Q C4AQ -1.6(4) . . . . ?
C7Q C6AQ C10Q N10Q 1.2(5) . . . . ?
C7Q C6AQ C10Q C11Q -175.9(3) . . . . ?
C7Q C8Q C9Q N10Q 1.1(5) . . . . ?
C8Q C9Q N10Q C10Q 0.4(5) . . . . ?
C9Q N10Q C10Q C6AQ -1.7(5) . . . . ?
C9Q N10Q C10Q C11Q 175.5(3) . . . . ?
N10Q C10Q C11Q N1Q -1.4(4) . . . . ?
N10Q C10Q C11Q C4AQ -178.8(3) . . . . ?
C10Q C6AQ C7Q C8Q 0.4(5) . . . . ?
C11Q N1Q C2Q C3Q -1.0(6) . . . . ?
C11Q C4AQ C5Q C6Q 1.0(5) . . . . ?
N1R C2R C3R C4R 0.4(9) . . . . ?
C2R N1R C11R C4AR 1.1(6) . . . . ?
C2R N1R C11R C10R -177.5(4) . . . . ?
C2R C3R C4R C4AR -1.3(9) . . . . ?
C3R C4R C4AR C5R 178.6(5) . . . . ?
C3R C4R C4AR C11R 2.0(7) . . . . ?
C4R C4AR C5R C6R -176.0(4) . . . . ?
C4R C4AR C11R N1R -2.0(6) . . . . ?
C4R C4AR C11R C10R 176.7(4) . . . . ?
C4AR C5R C6R C6AR -0.2(6) . . . . ?
C5R C4AR C11R N1R -178.6(4) . . . . ?
C5R C4AR C11R C10R 0.1(6) . . . . ?
C5R C6R C6AR C7R 178.1(4) . . . . ?
C5R C6R C6AR C10R -0.6(6) . . . . ?
C6R C6AR C7R C8R -177.0(4) . . . . ?
C6R C6AR C10R N10R 178.0(3) . . . . ?
C6R C6AR C10R C11R 1.1(5) . . . . ?
C6AR C7R C8R C9R -1.9(6) . . . . ?
C6AR C10R C11R N1R 177.8(3) . . . . ?
C6AR C10R C11R C4AR -0.8(5) . . . . ?
C7R C6AR C10R N10R -0.7(5) . . . . ?
C7R C6AR C10R C11R -177.6(3) . . . . ?
C7R C8R C9R N10R 1.4(6) . . . . ?
C8R C9R N10R C10R -0.4(5) . . . . ?
C9R N10R C10R C6AR 0.1(5) . . . . ?
C9R N10R C10R C11R 177.1(3) . . . . ?
N10R C10R C11R N1R 0.8(5) . . . . ?
N10R C10R C11R C4AR -177.9(3) . . . . ?
C10R C6AR C7R C8R 1.6(6) . . . . ?
C11R N1R C2R C3R -0.4(8) . . . . ?
C11R C4AR C5R C6R 0.5(6) . . . . ?

_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 1.788
_oxdiff_exptl_absorpt_empirical_full_min 0.656

_vrf_PLAT029_ATS-PHEN            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .
RESPONSE: Highly anisotropic unit cell made strategy difficult.
;
_vrf_PLAT915_ATS-PHEN            
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage
RESPONSE: Known correct absolute structure used.
;
####################################################################### 
# 
# 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_ATS-URE-MEOH
_database_code_depnum_ccdc_archive 'CCDC 2427257'
loop_
_audit_author_name
_audit_author_address
'Laszlo Fabian'
;University of East Anglia
United Kingdom
;
_audit_update_record             
;
2025-02-26 deposited with the CCDC.	2025-10-15 downloaded from the CCDC.
;
_audit_creation_date             2023-08-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec141 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'artesunate urea cocrystal methanol solvate'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H28 O8, C H4 N2 O, C H4 O'
_chemical_formula_sum            'C21 H36 N2 O10'
_chemical_formula_weight         476.52
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           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                   10.3625(5)
_cell_length_b                   7.3357(3)
_cell_length_c                   15.0315(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.125(4)
_cell_angle_gamma                90
_cell_volume                     1140.94(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3351
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.6330
_cell_measurement_theta_min      2.9430
_exptl_absorpt_coefficient_mu    0.929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7091
_diffrn_reflns_point_group_measured_fraction_full 0.810
_diffrn_reflns_point_group_measured_fraction_max 0.743
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.682
_diffrn_reflns_theta_min         2.944
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -26.00   0.50    0.11    --  -91.75  45.00-120.00   50
  2  ω    -50.00 -20.00   0.50    0.11    --  -91.75  45.00 -30.00   60
  3  ω    -50.00 -20.00   0.50    0.11    --  -91.75  45.00   0.00   60
  4  ω    -51.00 -24.00   0.50    0.11    --  -91.75  45.00  30.00   54
  5  ω    -62.00 -21.00   0.50    0.11    --  -91.75  61.00  30.00   82
  6  ω    -79.00 -43.00   0.50    0.11    --  -91.75  97.00  37.00   72
  7  ω     -2.00  25.00   0.50    0.05    --  -46.59  97.00  37.00   54
  8  ω    -59.00 -16.00   0.50    0.05    --  -46.59  97.00  37.00   86
  9  ω   -152.00 -87.00   0.50    0.11    --  -91.75 -97.00 -71.00  130
 10  ω   -163.00-121.00   0.50    0.11    --  -91.75 -77.00 -30.00   84
 11  ω    -22.00  27.00   0.50    0.05    --  -46.59  19.00-180.00   98
 12  ω    -24.00  29.00   0.50    0.05    --  -46.59  19.00 -60.00  106
 13  ω     12.00  37.00   0.50    0.05    --   46.59 -97.00 -71.00   50
 14  ω     38.00 103.00   0.50    0.11    --  106.59 -97.00 -71.00  130
 15  ω     39.00 104.00   0.50    0.11    --  106.59 -77.00 -60.00  130
 16  ω     39.00  68.00   0.50    0.11    --  106.59 -61.00-150.00   58
 17  ω    -24.00  24.00   0.50    0.05    --   46.59 -19.00  30.00   96
 18  ω    -22.00  24.00   0.50    0.05    --   46.59 -19.00 -90.00   92
 19  ω     38.00  63.00   0.50    0.11    --  106.59 -61.00  60.00   50
 20  ω     34.00  59.00   0.50    0.11    --  106.59 -61.00 120.00   50
 21  ω     35.00  70.00   0.50    0.11    --  106.59 -61.00 150.00   70
 22  ω    106.00 178.00   0.50    0.11    --  106.59  45.00 -30.00  144
 23  ω    120.00 147.00   0.50    0.11    --  106.59  97.00  37.00   54
 24  ω    102.00 127.00   0.50    0.11    --  106.59 125.00 150.00   50
 25  ω    142.00 170.00   0.50    0.11    --  106.59 125.00 150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0385668000
_diffrn_orient_matrix_UB_12      0.1888163000
_diffrn_orient_matrix_UB_13      0.0345587000
_diffrn_orient_matrix_UB_21      -0.1432571000
_diffrn_orient_matrix_UB_22      -0.0573361000
_diffrn_orient_matrix_UB_23      -0.0064947000
_diffrn_orient_matrix_UB_31      0.0129490000
_diffrn_orient_matrix_UB_32      -0.0719172000
_diffrn_orient_matrix_UB_33      0.0964032000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.489
_reflns_Friedel_fraction_full    0.610
_reflns_Friedel_fraction_max     0.531
_reflns_number_gt                3359
_reflns_number_total             3560
_reflns_odcompleteness_completeness 98.24
_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 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 1069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(17)
_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     304
_refine_ls_number_reflns         3560
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0466
_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)+(0.0752P)²+0.4122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1258
_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,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:
 C5A(H5AA), C6(H6), C8A(H8A), C9(H9), C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8B,H8C), C17(H17A,H17B), C18(H18A,
 H18B)
2.c X=CH2 refined with riding coordinates:
 N1U(H1UA,H1UB), N2U(H2UA,H2UB)
2.d Idealised Me refined as rotating group:
 C3M(H3MA,H3MB,H3MC), C6M(H6MA,H6MB,H6MC), C9M(H9MA,H9MB,H9MC), C1E(H1EA,H1EB,
 H1EC)
2.e Idealised tetrahedral OH refined as rotating group:
 O21(H21), O1E(H1E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2897(2) 0.3553(3) 0.13100(14) 0.0232(5) Uani 1 1 d . . . . .
O2 O 0.3248(2) 0.2433(3) 0.20945(14) 0.0242(5) Uani 1 1 d . . . . .
C3 C 0.2297(3) 0.2645(5) 0.2730(2) 0.0245(7) Uani 1 1 d . . . . .
C3M C 0.2634(4) 0.1223(5) 0.3423(2) 0.0300(8) Uani 1 1 d . . . . .
H3MA H 0.353921 0.129672 0.359342 0.045 Uiso 1 1 calc R U . . .
H3MB H 0.244026 0.003587 0.318223 0.045 Uiso 1 1 calc R U . . .
H3MC H 0.213949 0.142751 0.393486 0.045 Uiso 1 1 calc R U . . .
C4 C 0.0916(3) 0.2473(5) 0.2323(2) 0.0263(7) Uani 1 1 d . . . . .
H4A H 0.092673 0.170362 0.179904 0.032 Uiso 1 1 calc R U . . .
H4B H 0.039036 0.187008 0.274952 0.032 Uiso 1 1 calc R U . . .
C5 C 0.0285(3) 0.4290(5) 0.2060(2) 0.0258(7) Uani 1 1 d . . . . .
H5A H 0.020773 0.501173 0.259523 0.031 Uiso 1 1 calc R U . . .
H5B H -0.058334 0.404841 0.181396 0.031 Uiso 1 1 calc R U . . .
C5A C 0.0991(3) 0.5427(5) 0.1387(2) 0.0225(7) Uani 1 1 d . . . . .
H5AA H 0.080974 0.485693 0.080390 0.027 Uiso 1 1 calc R U . . .
C6 C 0.0450(3) 0.7380(5) 0.1316(2) 0.0234(7) Uani 1 1 d . . . . .
H6 H 0.060963 0.797602 0.189483 0.028 Uiso 1 1 calc R U . . .
C6M C -0.1008(3) 0.7430(6) 0.1080(2) 0.0301(8) Uani 1 1 d . . . . .
H6MA H -0.130485 0.866972 0.108579 0.045 Uiso 1 1 calc R U . . .
H6MB H -0.145084 0.673309 0.150966 0.045 Uiso 1 1 calc R U . . .
H6MC H -0.118024 0.692017 0.049774 0.045 Uiso 1 1 calc R U . . .
C7 C 0.1156(3) 0.8454(5) 0.0626(2) 0.0246(7) Uani 1 1 d . . . . .
H7A H 0.100915 0.788228 0.004783 0.030 Uiso 1 1 calc R U . . .
H7B H 0.080605 0.967996 0.058782 0.030 Uiso 1 1 calc R U . . .
C8 C 0.2598(3) 0.8553(5) 0.0857(2) 0.0249(7) Uani 1 1 d . . . . .
H8B H 0.274853 0.919845 0.141617 0.030 Uiso 1 1 calc R U . . .
H8C H 0.301286 0.923111 0.039818 0.030 Uiso 1 1 calc R U . . .
C8A C 0.3197(3) 0.6647(5) 0.0938(2) 0.0217(7) Uani 1 1 d . . . . .
H8A H 0.310482 0.609885 0.034350 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4663(3) 0.6681(5) 0.1198(2) 0.0221(7) Uani 1 1 d . . . . .
H9 H 0.499444 0.544049 0.113117 0.026 Uiso 1 1 calc R U . . .
C9M C 0.5414(3) 0.7927(6) 0.0601(2) 0.0284(8) Uani 1 1 d . . . . .
H9MA H 0.519768 0.917443 0.071668 0.043 Uiso 1 1 calc R U . . .
H9MB H 0.519329 0.764494 -0.001187 0.043 Uiso 1 1 calc R U . . .
H9MC H 0.632420 0.774732 0.072286 0.043 Uiso 1 1 calc R U . . .
C10 C 0.4844(3) 0.7191(5) 0.2174(2) 0.0216(6) Uani 1 1 d . . . . .
H10 H 0.449576 0.840926 0.227988 0.026 Uiso 1 1 calc R U . . .
O11 O 0.4252(2) 0.5874(3) 0.27072(14) 0.0213(5) Uani 1 1 d . . . . .
C12 C 0.2878(3) 0.5752(5) 0.2547(2) 0.0200(6) Uani 1 1 d . . . . .
H12 H 0.249585 0.691684 0.271381 0.024 Uiso 1 1 calc R U . . .
C12A C 0.2486(3) 0.5375(5) 0.1564(2) 0.0220(7) Uani 1 1 d . . . . .
O13 O 0.2482(2) 0.4412(3) 0.31371(14) 0.0221(5) Uani 1 1 d . . . . .
O14 O 0.6187(2) 0.7112(3) 0.24308(14) 0.0224(5) Uani 1 1 d . . . . .
C15 C 0.6566(3) 0.7860(5) 0.3228(2) 0.0216(7) Uani 1 1 d . . . . .
O16 O 0.5819(2) 0.8525(4) 0.37269(15) 0.0278(5) Uani 1 1 d . . . . .
C17 C 0.7993(3) 0.7677(5) 0.3405(2) 0.0237(7) Uani 1 1 d . . . . .
H17A H 0.843190 0.833545 0.295050 0.028 Uiso 1 1 calc R U . . .
H17B H 0.823030 0.640197 0.336546 0.028 Uiso 1 1 calc R U . . .
C18 C 0.8440(3) 0.8399(7) 0.4309(2) 0.0360(9) Uani 1 1 d . . . . .
H18A H 0.824164 0.968917 0.433578 0.043 Uiso 1 1 calc R U . . .
H18B H 0.796279 0.778821 0.476000 0.043 Uiso 1 1 calc R U . . .
C19 C 0.9859(3) 0.8138(6) 0.4522(2) 0.0274(8) Uani 1 1 d . . . . .
O20 O 1.0626(2) 0.7789(4) 0.39714(15) 0.0301(6) Uani 1 1 d . . . . .
O21 O 1.0180(2) 0.8401(6) 0.53754(16) 0.0455(8) Uani 1 1 d . . . . .
H21 H 1.095873 0.823953 0.546632 0.068 Uiso 1 1 calc R U . . .
C1U C 1.3548(3) 0.8212(5) 0.5370(2) 0.0254(7) Uani 1 1 d . . . . .
N1U N 1.3368(3) 0.7424(5) 0.45753(17) 0.0262(6) Uani 1 1 d . . . . .
H1UA H 1.261945 0.700217 0.440725 0.031 Uiso 1 1 calc R U . . .
H1UB H 1.399981 0.733627 0.422987 0.031 Uiso 1 1 calc R U . . .
O1U O 1.2635(2) 0.8353(4) 0.58858(15) 0.0306(6) Uani 1 1 d . . . . .
N2U N 1.4729(3) 0.8797(5) 0.5616(2) 0.0314(7) Uani 1 1 d . . . . .
H2UA H 1.487668 0.927885 0.613336 0.038 Uiso 1 1 calc R U . . .
H2UB H 1.534449 0.869277 0.525847 0.038 Uiso 1 1 calc R U . . .
C1E C 1.3264(4) 0.7360(7) 0.8177(3) 0.0361(8) Uani 1 1 d . . . . .
H1EA H 1.415189 0.726335 0.803134 0.054 Uiso 1 1 calc R U . . .
H1EB H 1.314998 0.677723 0.873918 0.054 Uiso 1 1 calc R U . . .
H1EC H 1.302974 0.862249 0.821515 0.054 Uiso 1 1 calc R U . . .
O1E O 1.2472(3) 0.6504(5) 0.75102(18) 0.0398(7) Uani 1 1 d . . . . .
H1E H 1.258888 0.697768 0.702697 0.060 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
O1 O2 1.466(3) . ?
O1 C12A 1.460(4) . ?
O2 C3 1.417(4) . ?
C3 C3M 1.502(5) . ?
C3 C4 1.530(5) . ?
C3 O13 1.442(4) . ?
C3M H3MA 0.9600 . ?
C3M H3MB 0.9600 . ?
C3M H3MC 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.527(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C5A 1.529(5) . ?
C5A H5AA 0.9800 . ?
C5A C6 1.540(5) . ?
C5A C12A 1.558(4) . ?
C6 H6 0.9800 . ?
C6 C6M 1.533(4) . ?
C6 C7 1.520(5) . ?
C6M H6MA 0.9600 . ?
C6M H6MB 0.9600 . ?
C6M H6MC 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.517(4) . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C8 C8A 1.532(5) . ?
C8A H8A 0.9800 . ?
C8A C9 1.548(4) . ?
C8A C12A 1.541(5) . ?
C9 H9 0.9800 . ?
C9 C9M 1.524(5) . ?
C9 C10 1.515(4) . ?
C9M H9MA 0.9600 . ?
C9M H9MB 0.9600 . ?
C9M H9MC 0.9600 . ?
C10 H10 0.9800 . ?
C10 O11 1.417(4) . ?
C10 O14 1.426(3) . ?
O11 C12 1.434(4) . ?
C12 H12 0.9800 . ?
C12 C12A 1.536(4) . ?
C12 O13 1.400(4) . ?
O14 C15 1.357(4) . ?
C15 O16 1.209(4) . ?
C15 C17 1.494(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.508(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.500(5) . ?
C19 O20 1.206(4) . ?
C19 O21 1.322(4) . ?
O21 H21 0.8200 . ?
C1U N1U 1.331(4) . ?
C1U O1U 1.260(4) . ?
C1U N2U 1.330(4) . ?
N1U H1UA 0.8600 . ?
N1U H1UB 0.8600 . ?
N2U H2UA 0.8600 . ?
N2U H2UB 0.8600 . ?
C1E H1EA 0.9600 . ?
C1E H1EB 0.9600 . ?
C1E H1EC 0.9600 . ?
C1E O1E 1.408(5) . ?
O1E H1E 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12A O1 O2 111.4(2) . . ?
C3 O2 O1 109.2(2) . . ?
O2 C3 C3M 104.3(3) . . ?
O2 C3 C4 113.0(3) . . ?
O2 C3 O13 107.7(3) . . ?
C3M C3 C4 113.4(3) . . ?
O13 C3 C3M 108.1(3) . . ?
O13 C3 C4 110.1(3) . . ?
C3 C3M H3MA 109.5 . . ?
C3 C3M H3MB 109.5 . . ?
C3 C3M H3MC 109.5 . . ?
H3MA C3M H3MB 109.5 . . ?
H3MA C3M H3MC 109.5 . . ?
H3MB C3M H3MC 109.5 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.2(3) . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C4 C5 H5A 108.4 . . ?
C4 C5 H5B 108.4 . . ?
C4 C5 C5A 115.7(3) . . ?
H5A C5 H5B 107.4 . . ?
C5A C5 H5A 108.4 . . ?
C5A C5 H5B 108.4 . . ?
C5 C5A H5AA 106.5 . . ?
C5 C5A C6 111.6(3) . . ?
C5 C5A C12A 112.4(3) . . ?
C6 C5A H5AA 106.5 . . ?
C6 C5A C12A 112.9(3) . . ?
C12A C5A H5AA 106.5 . . ?
C5A C6 H6 108.1 . . ?
C6M C6 C5A 112.9(3) . . ?
C6M C6 H6 108.1 . . ?
C7 C6 C5A 110.1(3) . . ?
C7 C6 H6 108.1 . . ?
C7 C6 C6M 109.5(3) . . ?
C6 C6M H6MA 109.5 . . ?
C6 C6M H6MB 109.5 . . ?
C6 C6M H6MC 109.5 . . ?
H6MA C6M H6MB 109.5 . . ?
H6MA C6M H6MC 109.5 . . ?
H6MB C6M H6MC 109.5 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C6 111.9(3) . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C7 C8 H8B 109.4 . . ?
C7 C8 H8C 109.4 . . ?
C7 C8 C8A 111.4(3) . . ?
H8B C8 H8C 108.0 . . ?
C8A C8 H8B 109.4 . . ?
C8A C8 H8C 109.4 . . ?
C8 C8A H8A 106.4 . . ?
C8 C8A C9 113.1(3) . . ?
C8 C8A C12A 113.3(3) . . ?
C9 C8A H8A 106.4 . . ?
C12A C8A H8A 106.4 . . ?
C12A C8A C9 110.5(3) . . ?
C8A C9 H9 107.7 . . ?
C9M C9 C8A 112.7(3) . . ?
C9M C9 H9 107.7 . . ?
C10 C9 C8A 108.4(2) . . ?
C10 C9 H9 107.7 . . ?
C10 C9 C9M 112.4(3) . . ?
C9 C9M H9MA 109.5 . . ?
C9 C9M H9MB 109.5 . . ?
C9 C9M H9MC 109.5 . . ?
H9MA C9M H9MB 109.5 . . ?
H9MA C9M H9MC 109.5 . . ?
H9MB C9M H9MC 109.5 . . ?
C9 C10 H10 110.8 . . ?
O11 C10 C9 110.2(3) . . ?
O11 C10 H10 110.8 . . ?
O11 C10 O14 105.4(2) . . ?
O14 C10 C9 108.6(2) . . ?
O14 C10 H10 110.8 . . ?
C10 O11 C12 113.9(2) . . ?
O11 C12 H12 108.3 . . ?
O11 C12 C12A 112.4(2) . . ?
C12A C12 H12 108.3 . . ?
O13 C12 O11 105.1(2) . . ?
O13 C12 H12 108.3 . . ?
O13 C12 C12A 114.3(3) . . ?
O1 C12A C5A 106.2(3) . . ?
O1 C12A C8A 103.8(2) . . ?
O1 C12A C12 110.6(3) . . ?
C8A C12A C5A 112.6(3) . . ?
C12 C12A C5A 111.6(3) . . ?
C12 C12A C8A 111.6(3) . . ?
C12 O13 C3 113.5(2) . . ?
C15 O14 C10 117.0(2) . . ?
O14 C15 C17 110.9(3) . . ?
O16 C15 O14 123.1(3) . . ?
O16 C15 C17 125.9(3) . . ?
C15 C17 H17A 109.1 . . ?
C15 C17 H17B 109.1 . . ?
C15 C17 C18 112.4(3) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C17 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 C17 113.4(3) . . ?
C19 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
O20 C19 C18 123.8(3) . . ?
O20 C19 O21 123.9(3) . . ?
O21 C19 C18 112.3(3) . . ?
C19 O21 H21 109.5 . . ?
O1U C1U N1U 121.0(3) . . ?
O1U C1U N2U 120.9(3) . . ?
N2U C1U N1U 118.2(3) . . ?
C1U N1U H1UA 120.0 . . ?
C1U N1U H1UB 120.0 . . ?
H1UA N1U H1UB 120.0 . . ?
C1U N2U H2UA 120.0 . . ?
C1U N2U H2UB 120.0 . . ?
H2UA N2U H2UB 120.0 . . ?
H1EA C1E H1EB 109.5 . . ?
H1EA C1E H1EC 109.5 . . ?
H1EB C1E H1EC 109.5 . . ?
O1E C1E H1EA 109.5 . . ?
O1E C1E H1EB 109.5 . . ?
O1E C1E H1EC 109.5 . . ?
C1E O1E H1E 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
O1 O2 C3 C3M 170.9(2) . . . . ?
O1 O2 C3 C4 47.3(4) . . . . ?
O1 O2 C3 O13 -74.5(3) . . . . ?
O2 O1 C12A C5A -106.2(3) . . . . ?
O2 O1 C12A C8A 134.8(2) . . . . ?
O2 O1 C12A C12 15.0(3) . . . . ?
O2 C3 C4 C5 -94.4(3) . . . . ?
O2 C3 O13 C12 35.7(3) . . . . ?
C3 C4 C5 C5A 58.5(4) . . . . ?
C3M C3 C4 C5 147.2(3) . . . . ?
C3M C3 O13 C12 147.8(3) . . . . ?
C4 C3 O13 C12 -87.9(3) . . . . ?
C4 C5 C5A C6 -167.9(3) . . . . ?
C4 C5 C5A C12A -39.9(4) . . . . ?
C5 C5A C6 C6M -56.0(4) . . . . ?
C5 C5A C6 C7 -178.7(3) . . . . ?
C5 C5A C12A O1 71.9(3) . . . . ?
C5 C5A C12A C8A -175.1(3) . . . . ?
C5 C5A C12A C12 -48.7(4) . . . . ?
C5A C6 C7 C8 -58.9(4) . . . . ?
C6 C5A C12A O1 -160.8(2) . . . . ?
C6 C5A C12A C8A -47.8(4) . . . . ?
C6 C5A C12A C12 78.7(3) . . . . ?
C6 C7 C8 C8A 58.2(4) . . . . ?
C6M C6 C7 C8 176.4(3) . . . . ?
C7 C8 C8A C9 -178.4(2) . . . . ?
C7 C8 C8A C12A -51.6(4) . . . . ?
C8 C8A C9 C9M -51.5(4) . . . . ?
C8 C8A C9 C10 73.7(3) . . . . ?
C8 C8A C12A O1 160.9(2) . . . . ?
C8 C8A C12A C5A 46.5(4) . . . . ?
C8 C8A C12A C12 -80.0(3) . . . . ?
C8A C9 C10 O11 61.4(4) . . . . ?
C8A C9 C10 O14 176.4(3) . . . . ?
C9 C8A C12A O1 -70.8(3) . . . . ?
C9 C8A C12A C5A 174.7(3) . . . . ?
C9 C8A C12A C12 48.3(4) . . . . ?
C9 C10 O11 C12 -63.2(3) . . . . ?
C9 C10 O14 C15 167.6(3) . . . . ?
C9M C9 C10 O11 -173.3(3) . . . . ?
C9M C9 C10 O14 -58.3(4) . . . . ?
C10 O11 C12 C12A 55.8(3) . . . . ?
C10 O11 C12 O13 -179.3(2) . . . . ?
C10 O14 C15 O16 2.2(5) . . . . ?
C10 O14 C15 C17 -179.9(3) . . . . ?
O11 C10 O14 C15 -74.4(3) . . . . ?
O11 C12 C12A O1 67.3(3) . . . . ?
O11 C12 C12A C5A -174.7(3) . . . . ?
O11 C12 C12A C8A -47.7(4) . . . . ?
O11 C12 O13 C3 -98.5(3) . . . . ?
C12A O1 O2 C3 45.1(3) . . . . ?
C12A C5A C6 C6M 176.2(3) . . . . ?
C12A C5A C6 C7 53.5(3) . . . . ?
C12A C8A C9 C9M -179.8(3) . . . . ?
C12A C8A C9 C10 -54.6(4) . . . . ?
C12A C12 O13 C3 25.2(4) . . . . ?
O13 C3 C4 C5 26.0(4) . . . . ?
O13 C12 C12A O1 -52.3(3) . . . . ?
O13 C12 C12A C5A 65.7(4) . . . . ?
O13 C12 C12A C8A -167.3(3) . . . . ?
O14 C10 O11 C12 179.7(2) . . . . ?
O14 C15 C17 C18 -176.8(3) . . . . ?
C15 C17 C18 C19 176.9(3) . . . . ?
O16 C15 C17 C18 1.0(5) . . . . ?
C17 C18 C19 O20 16.3(6) . . . . ?
C17 C18 C19 O21 -166.1(4) . . . . ?

_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 1.438
_oxdiff_exptl_absorpt_empirical_full_min 0.666
