# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 2151865'
loop_
_audit_author_name
_audit_author_address
'Andrew White'
;Imperial College London
United Kingdom
;
_audit_update_record             
;
2022-02-15 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H38 O4'
_chemical_formula_sum            'C27 H38 O4'
_chemical_formula_weight         426.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.1782(2)
_cell_length_b                   12.5203(3)
_cell_length_c                   19.0389(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2426.21(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9862
_cell_measurement_theta_min      2.7650
_cell_measurement_theta_max      27.7830

_exptl_crystal_description       blocks
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.655
_exptl_crystal_size_mid          0.488
_exptl_crystal_size_min          0.328
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            32494
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.579
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5467
_reflns_number_gt                4792
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     0.866
_reflns_Friedel_fraction_full    1.000

_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. 
;

_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+0.3874P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0078(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1813 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.3(4)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5467
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.52521(13) 0.80814(10) 0.67831(7) 0.0320(3) Uani 1 1 d . . . . .
C2 C 0.4157(2) 0.79153(17) 0.71809(10) 0.0316(4) Uani 1 1 d . . . . .
O2 O 0.35039(16) 0.86434(13) 0.73992(8) 0.0449(4) Uani 1 1 d . . . . .
C3 C 0.4005(2) 0.67261(17) 0.72815(10) 0.0320(5) Uani 1 1 d . . . . .
C4 C 0.5179(2) 0.6424(2) 0.77650(11) 0.0431(5) Uani 1 1 d . . . . .
H4A H 0.520313 0.688513 0.818734 0.052 Uiso 1 1 calc R U . . .
H4B H 0.512278 0.566825 0.791452 0.052 Uiso 1 1 calc R U . . .
C5 C 0.6398(2) 0.6613(2) 0.72991(10) 0.0377(5) Uani 1 1 d . . . . .
H5A H 0.699214 0.715267 0.750695 0.045 Uiso 1 1 calc R U . . .
H5B H 0.689081 0.594190 0.721952 0.045 Uiso 1 1 calc R U . . .
C6 C 0.57689(18) 0.70195(15) 0.66211(9) 0.0262(4) Uani 1 1 d . . . . .
C7 C 0.44907(17) 0.63470(14) 0.65479(9) 0.0243(4) Uani 1 1 d . . . . .
C8 C 0.3619(2) 0.67319(16) 0.59500(10) 0.0311(4) Uani 1 1 d . . . . .
H8A H 0.344139 0.749614 0.600761 0.047 Uiso 1 1 calc R U . . .
H8B H 0.278917 0.633574 0.595616 0.047 Uiso 1 1 calc R U . . .
H8C H 0.406669 0.661185 0.550104 0.047 Uiso 1 1 calc R U . . .
C9 C 0.4696(2) 0.51454(15) 0.64795(11) 0.0341(5) Uani 1 1 d . . . . .
H9A H 0.505512 0.498283 0.601396 0.051 Uiso 1 1 calc R U . . .
H9B H 0.385366 0.477780 0.653913 0.051 Uiso 1 1 calc R U . . .
H9C H 0.531260 0.490304 0.684151 0.051 Uiso 1 1 calc R U . . .
C10 C 0.2666(2) 0.6373(2) 0.75292(13) 0.0465(6) Uani 1 1 d . . . . .
H10A H 0.200657 0.656278 0.717578 0.070 Uiso 1 1 calc R U . . .
H10B H 0.245687 0.672896 0.797368 0.070 Uiso 1 1 calc R U . . .
H10C H 0.266616 0.559743 0.759909 0.070 Uiso 1 1 calc R U . . .
C11 C 0.66070(18) 0.70921(15) 0.59718(10) 0.0261(4) Uani 1 1 d . . . . .
O11 O 0.66713(14) 0.78286(11) 0.55734(8) 0.0385(4) Uani 1 1 d . . . . .
O12 O 0.72445(12) 0.61600(10) 0.58973(6) 0.0272(3) Uani 1 1 d . . . . .
C13 C 0.79525(18) 0.59902(15) 0.52376(9) 0.0252(4) Uani 1 1 d . . . . .
H13A H 0.851881 0.662556 0.513929 0.030 Uiso 1 1 calc R U . . .
C14 C 0.69859(18) 0.58701(15) 0.46684(10) 0.0280(4) Uani 1 1 d . . . . .
C15 C 0.61775(18) 0.57691(16) 0.42233(10) 0.0279(4) Uani 1 1 d . . . . .
C16 C 0.51492(19) 0.56214(15) 0.36846(10) 0.0284(4) Uani 1 1 d . . . . .
C17 C 0.3937(2) 0.51376(19) 0.40425(12) 0.0408(5) Uani 1 1 d . . . . .
H17A H 0.363651 0.561514 0.441747 0.061 Uiso 1 1 calc R U . . .
H17B H 0.416532 0.444101 0.424300 0.061 Uiso 1 1 calc R U . . .
H17C H 0.323380 0.504752 0.369576 0.061 Uiso 1 1 calc R U . . .
C18 C 0.4802(2) 0.66990(18) 0.33611(13) 0.0458(6) Uani 1 1 d . . . . .
H18A H 0.410703 0.660253 0.301055 0.069 Uiso 1 1 calc R U . . .
H18B H 0.558195 0.700293 0.313498 0.069 Uiso 1 1 calc R U . . .
H18C H 0.449381 0.718422 0.372990 0.069 Uiso 1 1 calc R U . . .
C19 C 0.5667(2) 0.4877(2) 0.31098(12) 0.0462(6) Uani 1 1 d . . . . .
H19A H 0.590701 0.418796 0.331744 0.069 Uiso 1 1 calc R U . . .
H19B H 0.644279 0.519837 0.288967 0.069 Uiso 1 1 calc R U . . .
H19C H 0.498375 0.476873 0.275436 0.069 Uiso 1 1 calc R U . . .
C20 C 0.88262(17) 0.50090(14) 0.53464(9) 0.0230(4) Uani 1 1 d . . . . .
C21 C 0.96308(19) 0.48115(16) 0.46726(10) 0.0292(4) Uani 1 1 d . . . . .
H21A H 0.902887 0.467821 0.427364 0.035 Uiso 1 1 calc R U . . .
H21B H 1.016227 0.545210 0.456229 0.035 Uiso 1 1 calc R U . . .
C22 C 0.97891(19) 0.52190(15) 0.59537(10) 0.0280(4) Uani 1 1 d . . . . .
H22A H 1.032367 0.585987 0.584830 0.034 Uiso 1 1 calc R U . . .
H22B H 0.929158 0.535565 0.639140 0.034 Uiso 1 1 calc R U . . .
C23 C 0.80142(18) 0.40077(15) 0.55109(10) 0.0278(4) Uani 1 1 d . . . . .
H23A H 0.749643 0.412427 0.594439 0.033 Uiso 1 1 calc R U . . .
H23B H 0.739418 0.386638 0.512121 0.033 Uiso 1 1 calc R U . . .
C24 C 1.05381(19) 0.38454(17) 0.47746(11) 0.0336(5) Uani 1 1 d . . . . .
H24A H 1.105401 0.372212 0.433501 0.040 Uiso 1 1 calc R U . . .
C25 C 1.1480(2) 0.40605(19) 0.53824(12) 0.0381(5) Uani 1 1 d . . . . .
H25A H 1.202449 0.469541 0.527613 0.046 Uiso 1 1 calc R U . . .
H25B H 1.207258 0.344127 0.544680 0.046 Uiso 1 1 calc R U . . .
C26 C 1.0692(2) 0.42525(17) 0.60558(11) 0.0348(5) Uani 1 1 d . . . . .
H26A H 1.130827 0.439284 0.645422 0.042 Uiso 1 1 calc R U . . .
C27 C 0.9860(2) 0.32647(17) 0.62203(12) 0.0404(5) Uani 1 1 d . . . . .
H27A H 1.043973 0.263999 0.629507 0.049 Uiso 1 1 calc R U . . .
H27B H 0.934958 0.338532 0.665571 0.049 Uiso 1 1 calc R U . . .
C28 C 0.8925(2) 0.30448(16) 0.56090(12) 0.0349(5) Uani 1 1 d . . . . .
H28A H 0.838701 0.239678 0.571623 0.042 Uiso 1 1 calc R U . . .
C29 C 0.9713(2) 0.28548(17) 0.49364(12) 0.0396(5) Uani 1 1 d . . . . .
H29A H 1.029397 0.222739 0.499694 0.048 Uiso 1 1 calc R U . . .
H29B H 0.910749 0.270828 0.454102 0.048 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 C2 1.364(2) . ?
O1 C6 1.463(2) . ?
C2 O2 1.202(2) . ?
C2 C3 1.509(3) . ?
C3 C10 1.508(3) . ?
C3 C4 1.555(3) . ?
C3 C7 1.556(3) . ?
C4 C5 1.543(3) . ?
C5 C6 1.528(3) . ?
C6 C11 1.505(3) . ?
C6 C7 1.556(3) . ?
C7 C8 1.521(3) . ?
C7 C9 1.525(3) . ?
C11 O11 1.196(2) . ?
C11 O12 1.343(2) . ?
O12 C13 1.464(2) . ?
C13 C14 1.471(3) . ?
C13 C20 1.531(2) . ?
C14 C15 1.188(3) . ?
C15 C16 1.477(3) . ?
C16 C18 1.525(3) . ?
C16 C19 1.531(3) . ?
C16 C17 1.534(3) . ?
C20 C23 1.534(2) . ?
C20 C22 1.538(2) . ?
C20 C21 1.542(3) . ?
C21 C24 1.534(3) . ?
C22 C26 1.532(3) . ?
C23 C28 1.532(3) . ?
C24 C25 1.527(3) . ?
C24 C29 1.529(3) . ?
C25 C26 1.531(3) . ?
C26 C27 1.531(3) . ?
C27 C28 1.528(3) . ?
C28 C29 1.530(3) . ?

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
C2 O1 C6 105.80(14) . . ?
O2 C2 O1 121.9(2) . . ?
O2 C2 C3 130.3(2) . . ?
O1 C2 C3 107.75(16) . . ?
C10 C3 C2 114.95(18) . . ?
C10 C3 C4 115.97(18) . . ?
C2 C3 C4 103.65(18) . . ?
C10 C3 C7 118.58(19) . . ?
C2 C3 C7 98.89(15) . . ?
C4 C3 C7 102.30(15) . . ?
C5 C4 C3 103.90(15) . . ?
C6 C5 C4 101.54(16) . . ?
O1 C6 C11 108.79(15) . . ?
O1 C6 C5 106.00(15) . . ?
C11 C6 C5 118.47(16) . . ?
O1 C6 C7 102.13(14) . . ?
C11 C6 C7 115.67(15) . . ?
C5 C6 C7 104.20(16) . . ?
C8 C7 C9 109.19(16) . . ?
C8 C7 C3 112.95(15) . . ?
C9 C7 C3 114.92(16) . . ?
C8 C7 C6 112.52(15) . . ?
C9 C7 C6 115.27(15) . . ?
C3 C7 C6 91.16(14) . . ?
O11 C11 O12 125.21(18) . . ?
O11 C11 C6 126.78(17) . . ?
O12 C11 C6 107.96(15) . . ?
C11 O12 C13 117.06(14) . . ?
O12 C13 C14 108.52(14) . . ?
O12 C13 C20 106.64(14) . . ?
C14 C13 C20 113.96(15) . . ?
C15 C14 C13 178.1(2) . . ?
C14 C15 C16 178.2(2) . . ?
C15 C16 C18 109.51(16) . . ?
C15 C16 C19 109.17(17) . . ?
C18 C16 C19 109.25(18) . . ?
C15 C16 C17 108.12(16) . . ?
C18 C16 C17 110.02(18) . . ?
C19 C16 C17 110.74(17) . . ?
C13 C20 C23 111.75(14) . . ?
C13 C20 C22 109.55(15) . . ?
C23 C20 C22 109.24(15) . . ?
C13 C20 C21 108.94(15) . . ?
C23 C20 C21 108.96(15) . . ?
C22 C20 C21 108.33(14) . . ?
C24 C21 C20 109.93(16) . . ?
C26 C22 C20 110.03(15) . . ?
C28 C23 C20 109.99(14) . . ?
C25 C24 C29 109.59(18) . . ?
C25 C24 C21 109.56(16) . . ?
C29 C24 C21 109.54(16) . . ?
C24 C25 C26 109.48(16) . . ?
C27 C26 C25 109.51(18) . . ?
C27 C26 C22 109.43(16) . . ?
C25 C26 C22 109.38(17) . . ?
C28 C27 C26 109.52(17) . . ?
C27 C28 C29 109.82(17) . . ?
C27 C28 C23 109.14(17) . . ?
C29 C28 C23 109.73(17) . . ?
C24 C29 C28 109.30(16) . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.035

