# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

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

data_7002
_database_code_depnum_ccdc_archive 'CCDC 2072549'
loop_
_audit_author_name
_audit_author_address
'Kirsten Christensen'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-09-15 downloaded from the CCDC.
;
_audit_creation_date             2018-08-16
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 7002
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_refine_special_details          
; 
During final refinement two hydrogens positions came too
close to each other. Several attempts were made to rotate the
CH3-groups away from each other, but the optimal refinement 
placed them in this position.

       Flack Parameter & su -0.034  0.151  @ 

 Using counting statistics weights
       Hooft Parameter & su -0.067  0.087  $ 
           Hole-in-one & su -0.065  0.083    
    Bijvoet Difference & su -0.053  0.088  ?  
(Using  2288 reflections. Correl Coef =  12%)

 Histogram re-weighted,  1759 reflections,  
12.6% within interval x= -.5 to 1.5
    Bijvoet Difference & su -0.082  0.088    
 Average of Ratios (x) & su -0.082  0.082  & 
 Average of Ratios (x) & su -0.082  0.083  %  
(corrected for npp, * 1.00)


@  Flack,1983, Acta Cryst A39, 876-881
?  Thompson & Watkin, 2011, J Appl Cryst, 44, 1077-1022
$  Hooft et al, 2008, J Appl Cryst, 41, 96-103
&  Cooper et al, to be published

 Hooft probability analysis
 For an enantiopure material, there are 2 choices, P2
 P2(correct)     1.0000   i.e. 0.100000E+01                                     

 If 50:50 twinning is possible, there are 3 choices, P3
 P3(correct)     1.0000   i.e. 0.100000E+01                                     
 P3(rac-twin)    0.0000   i.e. 0.938381E-09                                     
 P3(inverse)     0.0000   i.e. 0.503561E-32                                     
 G              1.1337                                                          
 G S.U.         0.1746  
;

_cell_length_a                   14.0413(3)
_cell_length_b                   7.0334(2)
_cell_length_c                   27.4163(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2707.58(13)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21 '
_symmetry_space_group_name_Hall  'P 2c -2ac'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,z+1/2
-x+1/2,y,z+1/2
x+1/2,-y,z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C15 H16 O5 
# Dc =      1.36 Fooo =   1168.00 Mu =      8.51 M =    276.29
# Found Formula = C15 H16.00 O5 
# Dc =      1.36 FOOO =   1167.99 Mu =      8.51 M =    276.29

_chemical_formula_sum            'C15 H16 O5'
_chemical_formula_moiety         'C15 H16 O5'
_chemical_compound_source        .
_chemical_formula_weight         276.29


_cell_measurement_reflns_used    5831
_cell_measurement_theta_min      6
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       lath
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.03
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.21

_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1167.994
_exptl_absorpt_coefficient_mu    0.851

# Sheldrick geometric approximatio 0.86 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            13755
_reflns_number_total             5388
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_sigmaI/netI    0.0409
# Number of reflections without Friedels Law is 5388 
# Number of reflections with Friedels Law is 2893 
# Theoretical number of reflections is about 2850 


_diffrn_reflns_theta_min         3.224
_diffrn_reflns_theta_max         76.653
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        76.653
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_reflns_limit_h_min              0
_reflns_limit_h_max              17
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              -34
_reflns_limit_l_max              33

_oxford_diffrn_Wilson_B_factor   2.66
_oxford_diffrn_Wilson_scale      0.04

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.18
_refine_diff_density_max         0.25


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     1
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5386
_oxford_refine_ls_R_factor_ref   0.0390
_refine_ls_wR_factor_ref         0.0949
_refine_ls_goodness_of_fit_ref   0.9983
_refine_ls_shift/su_max          0.0004106
_refine_ls_shift/su_mean         0.0000546


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5387
_refine_ls_R_factor_all          0.0391
_refine_ls_wR_factor_all         0.0950

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4983
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_gt          0.0906

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661--683 
_oxford_Hooft_y                  -0.07(9) # for 2288 Friedel pairs 
_oxford_Bijvoet_difference       -0.05(9) # for 2288 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          -0.03(15) # for 2495 Friedel pairs 
_refine_ls_abs_structure_Flack   -0.05(9)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 2288 Friedel Pairs 
;

# choose from: 
# rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.62P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.59456(15) 0.3292(3) 0.49998(9) 0.0334 1.0000 Uani . . . . . .
O2 O 0.67776(10) 0.3733(2) 0.52930(7) 0.0347 1.0000 Uani . . . . . .
C3 C 0.70288(14) 0.5560(3) 0.51893(8) 0.0305 1.0000 Uani . . . . . .
C4 C 0.77549(15) 0.6552(3) 0.54253(9) 0.0369 1.0000 Uani . . . . . .
C5 C 0.79433(15) 0.8380(3) 0.52661(9) 0.0401 1.0000 Uani . . . . . .
C6 C 0.74370(15) 0.9202(3) 0.48862(9) 0.0369 1.0000 Uani . . . . . .
C7 C 0.67175(14) 0.8191(3) 0.46509(9) 0.0308 1.0000 Uani . . . . . .
C8 C 0.65090(13) 0.6368(3) 0.48123(8) 0.0258 1.0000 Uani . . . . . .
C9 C 0.58439(12) 0.4843(3) 0.46052(8) 0.0249 1.0000 Uani . . . . . .
C10 C 0.47964(13) 0.5401(3) 0.45519(8) 0.0272 1.0000 Uani . . . . . .
C11 C 0.63535(12) 0.4275(3) 0.41331(8) 0.0272 1.0000 Uani . . . . . .
O12 O 0.70069(10) 0.3174(2) 0.41211(7) 0.0395 1.0000 Uani . . . . . .
O13 O 0.60633(10) 0.5331(2) 0.37550(6) 0.0338 1.0000 Uani . . . . . .
C14 C 0.66566(19) 0.5196(4) 0.33235(10) 0.0495 1.0000 Uani . . . . . .
C15 C 0.44799(16) 0.7148(3) 0.48223(10) 0.0422 1.0000 Uani . . . . . .
C21 C 0.41432(13) 0.4361(3) 0.43161(8) 0.0303 1.0000 Uani . . . . . .
C22 C 0.43103(13) 0.2520(3) 0.40757(8) 0.0293 1.0000 Uani . . . . . .
O23 O 0.50236(10) 0.1571(2) 0.40983(7) 0.0369 1.0000 Uani . . . . . .
O24 O 0.35334(10) 0.1990(2) 0.38235(7) 0.0410 1.0000 Uani . . . . . .
C25 C 0.35609(17) 0.0124(4) 0.36037(11) 0.0508 1.0000 Uani . . . . . .
C51 C 0.81883(14) 0.1771(3) 0.64585(8) 0.0284 1.0000 Uani . . . . . .
O52 O 0.90652(10) 0.13755(19) 0.61958(6) 0.0307 1.0000 Uani . . . . . .
C53 C 0.93225(13) -0.0444(3) 0.63109(8) 0.0262 1.0000 Uani . . . . . .
C54 C 1.00797(14) -0.1388(3) 0.60973(8) 0.0317 1.0000 Uani . . . . . .
C55 C 1.02667(14) -0.3231(3) 0.62579(9) 0.0341 1.0000 Uani . . . . . .
C56 C 0.97210(14) -0.4076(3) 0.66196(9) 0.0323 1.0000 Uani . . . . . .
C57 C 0.89742(13) -0.3080(3) 0.68394(8) 0.0286 1.0000 Uani . . . . . .
C58 C 0.87732(12) -0.1255(3) 0.66754(8) 0.0244 1.0000 Uani . . . . . .
C59 C 0.80930(12) 0.0271(2) 0.68711(8) 0.0237 1.0000 Uani . . . . . .
C60 C 0.70514(13) -0.0315(3) 0.69380(8) 0.0268 1.0000 Uani . . . . . .
C61 C 0.86094(12) 0.0912(3) 0.73328(8) 0.0267 1.0000 Uani . . . . . .
O62 O 0.92530(10) 0.2040(2) 0.73334(7) 0.0356 1.0000 Uani . . . . . .
O63 O 0.83448(10) -0.0106(2) 0.77209(6) 0.0326 1.0000 Uani . . . . . .
C64 C 0.89564(17) 0.0083(4) 0.81464(10) 0.0446 1.0000 Uani . . . . . .
C65 C 0.67307(14) -0.2083(3) 0.66752(10) 0.0364 1.0000 Uani . . . . . .
C71 C 0.64069(13) 0.0712(3) 0.71811(8) 0.0288 1.0000 Uani . . . . . .
C72 C 0.65698(13) 0.2551(3) 0.74193(8) 0.0293 1.0000 Uani . . . . . .
O73 O 0.72628(10) 0.3552(2) 0.73751(7) 0.0359 1.0000 Uani . . . . . .
O74 O 0.58180(10) 0.3030(2) 0.76963(7) 0.0400 1.0000 Uani . . . . . .
C75 C 0.58424(17) 0.4906(4) 0.79152(11) 0.0531 1.0000 Uani . . . . . .
H12 H 0.5398 0.3328 0.5220 0.0407 1.0000 Uiso R . . . . .
H11 H 0.6042 0.2068 0.4844 0.0389 1.0000 Uiso R . . . . .
H41 H 0.8099 0.5993 0.5677 0.0438 1.0000 Uiso R . . . . .
H51 H 0.8422 0.9079 0.5416 0.0486 1.0000 Uiso R . . . . .
H61 H 0.7561 1.0481 0.4785 0.0434 1.0000 Uiso R . . . . .
H71 H 0.6361 0.8753 0.4387 0.0367 1.0000 Uiso R . . . . .
H152 H 0.3800 0.7228 0.4807 0.0629 1.0000 Uiso R . . . . .
H153 H 0.4694 0.7109 0.5168 0.0626 1.0000 Uiso R . . . . .
H151 H 0.4742 0.8272 0.4674 0.0621 1.0000 Uiso R . . . . .
H211 H 0.3522 0.4830 0.4304 0.0371 1.0000 Uiso R . . . . .
H252 H 0.3163 0.0217 0.3309 0.0764 1.0000 Uiso R . . . . .
H253 H 0.3291 -0.0800 0.3842 0.0772 1.0000 Uiso R . . . . .
H251 H 0.4195 -0.0230 0.3526 0.0766 1.0000 Uiso R . . . . .
H512 H 0.8212 0.3054 0.6578 0.0338 1.0000 Uiso R . . . . .
H511 H 0.7657 0.1633 0.6231 0.0335 1.0000 Uiso R . . . . .
H541 H 1.0447 -0.0788 0.5863 0.0379 1.0000 Uiso R . . . . .
H551 H 1.0772 -0.3904 0.6127 0.0415 1.0000 Uiso R . . . . .
H561 H 0.9871 -0.5356 0.6725 0.0383 1.0000 Uiso R . . . . .
H571 H 0.8612 -0.3643 0.7099 0.0345 1.0000 Uiso R . . . . .
H652 H 0.6047 -0.2189 0.6687 0.0540 1.0000 Uiso R . . . . .
H653 H 0.7019 -0.3193 0.6830 0.0542 1.0000 Uiso R . . . . .
H651 H 0.6962 -0.2052 0.6335 0.0544 1.0000 Uiso R . . . . .
H711 H 0.5776 0.0269 0.7202 0.0350 1.0000 Uiso R . . . . .
H752 H 0.5257 0.5522 0.7863 0.0807 1.0000 Uiso R . . . . .
H753 H 0.5960 0.4685 0.8245 0.0802 1.0000 Uiso R . . . . .
H751 H 0.6357 0.5646 0.7776 0.0800 1.0000 Uiso R . . . . .
H141 H 0.6350 0.5999 0.3086 0.0739 1.0000 Uiso R . . . . .
H142 H 0.7279 0.5710 0.3407 0.0745 1.0000 Uiso R . . . . .
H143 H 0.6688 0.3911 0.3202 0.0741 1.0000 Uiso R . . . . .
H641 H 0.8610 -0.0438 0.8425 0.0664 1.0000 Uiso R . . . . .
H642 H 0.9160 0.1414 0.8205 0.0672 1.0000 Uiso R . . . . .
H643 H 0.9509 -0.0717 0.8094 0.0678 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.25(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . O2 . 1.452(2) yes
C1 . C9 . 1.543(3) yes
C1 . H12 . 0.977 no
C1 . H11 . 0.970 no
O2 . C3 . 1.363(3) yes
C3 . C4 . 1.395(3) yes
C3 . C8 . 1.387(3) yes
C4 . C5 . 1.383(3) yes
C4 . H41 . 0.930 no
C5 . C6 . 1.387(3) yes
C5 . H51 . 0.928 no
C6 . C7 . 1.394(3) yes
C6 . H61 . 0.957 no
C7 . C8 . 1.388(3) yes
C7 . H71 . 0.964 no
C8 . C9 . 1.531(3) yes
C9 . C10 . 1.529(2) yes
C9 . C11 . 1.532(3) yes
C10 . C15 . 1.502(3) yes
C10 . C21 . 1.339(3) yes
C11 . O12 . 1.201(2) yes
C11 . O13 . 1.338(3) yes
O13 . C14 . 1.450(2) yes
C14 . H141 . 0.963 no
C14 . H142 . 0.973 no
C14 . H143 . 0.965 no
C15 . H152 . 0.958 no
C15 . H153 . 0.995 no
C15 . H151 . 0.962 no
C21 . C22 . 1.472(3) yes
C21 . H211 . 0.933 no
C22 . O23 . 1.205(2) yes
C22 . O24 . 1.344(2) yes
O24 . C25 . 1.445(3) yes
C25 . H252 . 0.984 no
C25 . H253 . 0.996 no
C25 . H251 . 0.948 no
C51 . O52 . 1.453(2) yes
C51 . C59 . 1.553(3) yes
C51 . H512 . 0.961 no
C51 . H511 . 0.977 no
O52 . C53 . 1.367(2) yes
C53 . C54 . 1.383(3) yes
C53 . C58 . 1.385(3) yes
C54 . C55 . 1.394(3) yes
C54 . H541 . 0.926 no
C55 . C56 . 1.387(3) yes
C55 . H551 . 0.925 no
C56 . C57 . 1.398(3) yes
C56 . H561 . 0.968 no
C57 . C58 . 1.389(3) yes
C57 . H571 . 0.960 no
C58 . C59 . 1.534(2) yes
C59 . C60 . 1.531(2) yes
C59 . C61 . 1.527(3) yes
C60 . C65 . 1.506(3) yes
C60 . C71 . 1.336(3) yes
C61 . O62 . 1.202(2) yes
C61 . O63 . 1.335(3) yes
O63 . C64 . 1.455(2) yes
C64 . H641 . 0.978 no
C64 . H642 . 0.992 no
C64 . H643 . 0.969 no
C65 . H652 . 0.963 no
C65 . H653 . 0.977 no
C65 . H651 . 0.987 no
C71 . C72 . 1.467(3) yes
C71 . H711 . 0.941 no
C72 . O73 . 1.207(2) yes
C72 . O74 . 1.343(2) yes
O74 . C75 . 1.450(3) yes
C75 . H752 . 0.940 no
C75 . H753 . 0.933 no
C75 . H751 . 0.968 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . C1 . C9 . 108.15(16) yes
O2 . C1 . H12 . 106.6 no
C9 . C1 . H12 . 110.0 no
O2 . C1 . H11 . 108.7 no
C9 . C1 . H11 . 109.4 no
H12 . C1 . H11 . 113.8 no
C1 . O2 . C3 . 107.12(16) yes
O2 . C3 . C4 . 124.34(19) yes
O2 . C3 . C8 . 113.92(18) yes
C4 . C3 . C8 . 121.7(2) yes
C3 . C4 . C5 . 117.3(2) yes
C3 . C4 . H41 . 120.8 no
C5 . C4 . H41 . 121.9 no
C4 . C5 . C6 . 121.8(2) yes
C4 . C5 . H51 . 119.5 no
C6 . C5 . H51 . 118.8 no
C5 . C6 . C7 . 120.4(2) yes
C5 . C6 . H61 . 121.0 no
C7 . C6 . H61 . 118.6 no
C6 . C7 . C8 . 118.5(2) yes
C6 . C7 . H71 . 121.0 no
C8 . C7 . H71 . 120.5 no
C7 . C8 . C3 . 120.33(18) yes
C7 . C8 . C9 . 131.12(18) yes
C3 . C8 . C9 . 108.09(17) yes
C1 . C9 . C8 . 100.30(15) yes
C1 . C9 . C10 . 109.71(15) yes
C8 . C9 . C10 . 116.26(15) yes
C1 . C9 . C11 . 111.40(16) yes
C8 . C9 . C11 . 102.17(14) yes
C10 . C9 . C11 . 115.82(16) yes
C9 . C10 . C15 . 116.57(17) yes
C9 . C10 . C21 . 124.38(17) yes
C15 . C10 . C21 . 118.83(18) yes
C9 . C11 . O12 . 123.23(19) yes
C9 . C11 . O13 . 111.57(15) yes
O12 . C11 . O13 . 124.67(19) yes
C11 . O13 . C14 . 114.89(18) yes
O13 . C14 . H141 . 104.8 no
O13 . C14 . H142 . 107.4 no
H141 . C14 . H142 . 110.0 no
O13 . C14 . H143 . 111.7 no
H141 . C14 . H143 . 109.6 no
H142 . C14 . H143 . 112.8 no
C10 . C15 . H152 . 108.8 no
C10 . C15 . H153 . 111.0 no
H152 . C15 . H153 . 110.1 no
C10 . C15 . H151 . 110.5 no
H152 . C15 . H151 . 108.4 no
H153 . C15 . H151 . 108.0 no
C10 . C21 . C22 . 125.97(17) yes
C10 . C21 . H211 . 117.6 no
C22 . C21 . H211 . 116.4 no
C21 . C22 . O23 . 126.63(18) yes
C21 . C22 . O24 . 110.17(17) yes
O23 . C22 . O24 . 123.19(19) yes
C22 . O24 . C25 . 116.40(18) yes
O24 . C25 . H252 . 105.5 no
O24 . C25 . H253 . 108.0 no
H252 . C25 . H253 . 111.5 no
O24 . C25 . H251 . 110.9 no
H252 . C25 . H251 . 111.5 no
H253 . C25 . H251 . 109.4 no
O52 . C51 . C59 . 107.68(15) yes
O52 . C51 . H512 . 108.7 no
C59 . C51 . H512 . 113.1 no
O52 . C51 . H511 . 108.2 no
C59 . C51 . H511 . 109.3 no
H512 . C51 . H511 . 109.8 no
C51 . O52 . C53 . 106.79(15) yes
O52 . C53 . C54 . 123.68(19) yes
O52 . C53 . C58 . 113.89(17) yes
C54 . C53 . C58 . 122.40(18) yes
C53 . C54 . C55 . 117.21(19) yes
C53 . C54 . H541 . 120.2 no
C55 . C54 . H541 . 122.5 no
C54 . C55 . C56 . 121.37(19) yes
C54 . C55 . H551 . 119.9 no
C56 . C55 . H551 . 118.8 no
C55 . C56 . C57 . 120.49(19) yes
C55 . C56 . H561 . 119.5 no
C57 . C56 . H561 . 120.0 no
C56 . C57 . C58 . 118.44(19) yes
C56 . C57 . H571 . 120.6 no
C58 . C57 . H571 . 120.9 no
C57 . C58 . C53 . 120.06(17) yes
C57 . C58 . C59 . 131.30(18) yes
C53 . C58 . C59 . 108.11(16) yes
C58 . C59 . C51 . 99.63(15) yes
C58 . C59 . C60 . 116.65(14) yes
C51 . C59 . C60 . 110.65(15) yes
C58 . C59 . C61 . 101.59(14) yes
C51 . C59 . C61 . 111.24(15) yes
C60 . C59 . C61 . 115.72(16) yes
C59 . C60 . C65 . 116.79(16) yes
C59 . C60 . C71 . 124.15(17) yes
C65 . C60 . C71 . 118.86(17) yes
C59 . C61 . O62 . 123.56(18) yes
C59 . C61 . O63 . 111.73(15) yes
O62 . C61 . O63 . 124.18(18) yes
C61 . O63 . C64 . 115.20(17) yes
O63 . C64 . H641 . 107.4 no
O63 . C64 . H642 . 112.7 no
H641 . C64 . H642 . 111.7 no
O63 . C64 . H643 . 107.6 no
H641 . C64 . H643 . 107.2 no
H642 . C64 . H643 . 110.0 no
C60 . C65 . H652 . 110.2 no
C60 . C65 . H653 . 109.1 no
H652 . C65 . H653 . 109.7 no
C60 . C65 . H651 . 109.6 no
H652 . C65 . H651 . 111.2 no
H653 . C65 . H651 . 107.0 no
C60 . C71 . C72 . 126.39(17) yes
C60 . C71 . H711 . 119.2 no
C72 . C71 . H711 . 114.4 no
C71 . C72 . O73 . 126.53(18) yes
C71 . C72 . O74 . 110.50(16) yes
O73 . C72 . O74 . 122.96(19) yes
C72 . O74 . C75 . 116.34(17) yes
O74 . C75 . H752 . 109.6 no
O74 . C75 . H753 . 104.7 no
H752 . C75 . H753 . 112.3 no
O74 . C75 . H751 . 110.1 no
H752 . C75 . H751 . 110.1 no
H753 . C75 . H751 . 109.8 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C21 . H211 . O12 4_465 164 0.93 2.60 3.506(3) yes
C25 . H253 . O12 4_455 152 1.00 2.57 3.486(3) yes

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
5 2 31 x .

