# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_Compound-18
_database_code_depnum_ccdc_archive 'CCDC 1883091'
loop_
_audit_author_name
_audit_author_address
'Changqing Ye'
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2018-12-04 deposited with the CCDC.	2019-02-18 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         ?
_chemical_formula_sum            'C44 H46 O4'
_chemical_formula_weight         638.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   10.8484(4)
_cell_length_b                   11.0591(5)
_cell_length_c                   15.2489(6)
_cell_angle_alpha                76.980(4)
_cell_angle_beta                 84.293(3)
_cell_angle_gamma                86.909(3)
_cell_volume                     1772.66(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    99.99(10)
_cell_measurement_reflns_used    16446
_cell_measurement_theta_min      2.5820
_cell_measurement_theta_max      60.3760

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_F_000             684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.374
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.81422
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      99.99(10)
_diffrn_radiation_wavelength     1.3405
_diffrn_radiation_type           GaK\a
_diffrn_source                   'micro-focus metaljet'
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24617
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.596
_diffrn_reflns_theta_max         60.549
_diffrn_reflns_theta_full        53.543
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7932
_reflns_number_gt                6775
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 1.171.40.14a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0622P)²+0.5622P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7932
_refine_ls_number_parameters     439
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 0.26564(10) 0.13322(10) 0.88722(7) 0.0358(2) Uani 1 1 d . . . . .
O2 O 0.12821(9) 0.22827(10) 0.79230(7) 0.0352(2) Uani 1 1 d . . . . .
O3 O -0.04059(10) 0.37836(11) 0.12466(8) 0.0422(3) Uani 1 1 d . . . . .
O4 O -0.04845(9) 0.22001(10) 0.05721(7) 0.0340(2) Uani 1 1 d . . . . .
C1 C 0.02717(15) 0.50031(17) 0.30423(12) 0.0422(4) Uani 1 1 d . . . . .
H1A H -0.040066 0.541801 0.332693 0.063 Uiso 1 1 calc R U . . .
H1B H 0.001372 0.420741 0.298998 0.063 Uiso 1 1 calc R U . . .
H1C H 0.050839 0.549497 0.245157 0.063 Uiso 1 1 calc R U . . .
C2 C 0.13597(13) 0.48287(13) 0.36046(9) 0.0281(3) Uani 1 1 d . . . . .
C3 C 0.24030(13) 0.41173(12) 0.34056(9) 0.0270(3) Uani 1 1 d . . . . .
H3 H 0.242817 0.373445 0.291976 0.032 Uiso 1 1 calc R U . . .
C4 C 0.34097(12) 0.39705(12) 0.39234(8) 0.0236(3) Uani 1 1 d . . . . .
H4 H 0.409491 0.349031 0.377380 0.028 Uiso 1 1 calc R U . . .
C5 C 0.34219(11) 0.45202(11) 0.46574(8) 0.0211(2) Uani 1 1 d . . . . .
C6 C 0.23649(12) 0.52280(11) 0.48598(9) 0.0237(3) Uani 1 1 d . . . . .
H6 H 0.233322 0.560179 0.535062 0.028 Uiso 1 1 calc R U . . .
C7 C 0.13648(12) 0.53800(12) 0.43397(9) 0.0271(3) Uani 1 1 d . . . . .
H7 H 0.067998 0.586293 0.448603 0.032 Uiso 1 1 calc R U . . .
C8 C 0.45663(11) 0.44012(11) 0.51958(8) 0.0209(2) Uani 1 1 d . . . . .
C9 C 0.42028(12) 0.43014(11) 0.62168(8) 0.0223(3) Uani 1 1 d . . . . .
H9A H 0.495513 0.420099 0.652410 0.027 Uiso 1 1 calc R U . . .
H9B H 0.379563 0.507744 0.629520 0.027 Uiso 1 1 calc R U . . .
C10 C 0.33551(12) 0.32436(12) 0.66737(8) 0.0238(3) Uani 1 1 d . . . . .
H10A H 0.368096 0.247619 0.652011 0.029 Uiso 1 1 calc R U . . .
H10B H 0.253646 0.341542 0.646128 0.029 Uiso 1 1 calc R U . . .
C11 C 0.32664(13) 0.31035(14) 0.76989(9) 0.0307(3) Uani 1 1 d . . . . .
H11A H 0.408869 0.290560 0.790015 0.037 Uiso 1 1 calc R U . . .
H11B H 0.299785 0.389712 0.783524 0.037 Uiso 1 1 calc R U . . .
C12 C 0.24027(13) 0.21304(13) 0.82338(8) 0.0262(3) Uani 1 1 d . . . . .
C13 C 0.03378(15) 0.14534(16) 0.84054(11) 0.0402(4) Uani 1 1 d . . . . .
H13A H 0.052432 0.063486 0.830376 0.060 Uiso 1 1 calc R U . . .
H13B H -0.045280 0.174352 0.819362 0.060 Uiso 1 1 calc R U . . .
H13C H 0.031315 0.142955 0.904015 0.060 Uiso 1 1 calc R U . . .
C14 C 0.53235(12) 0.32867(11) 0.50849(8) 0.0220(2) Uani 1 1 d . . . . .
C15 C 0.59763(12) 0.24147(11) 0.49810(8) 0.0227(3) Uani 1 1 d . . . . .
C16 C 0.68196(12) 0.14206(12) 0.48188(9) 0.0228(3) Uani 1 1 d . . . . .
C17 C 0.65918(14) 0.01857(12) 0.52333(9) 0.0290(3) Uani 1 1 d . . . . .
H17 H 0.588773 -0.000704 0.563170 0.035 Uiso 1 1 calc R U . . .
C18 C 0.74075(15) -0.07591(13) 0.50563(10) 0.0326(3) Uani 1 1 d . . . . .
H18 H 0.723901 -0.157701 0.534075 0.039 Uiso 1 1 calc R U . . .
C19 C 0.84645(14) -0.05143(14) 0.44675(10) 0.0320(3) Uani 1 1 d . . . . .
C20 C 0.86943(13) 0.07223(15) 0.40539(12) 0.0368(3) Uani 1 1 d . . . . .
H20 H 0.940207 0.091159 0.365875 0.044 Uiso 1 1 calc R U . . .
C21 C 0.78829(13) 0.16742(13) 0.42230(11) 0.0317(3) Uani 1 1 d . . . . .
H21 H 0.805021 0.249125 0.393555 0.038 Uiso 1 1 calc R U . . .
C22 C 0.93293(17) -0.15576(17) 0.42776(13) 0.0463(4) Uani 1 1 d . . . . .
H22A H 0.910186 -0.231740 0.469451 0.069 Uiso 1 1 calc R U . . .
H22B H 1.016456 -0.137410 0.434641 0.069 Uiso 1 1 calc R U . . .
H22C H 0.927194 -0.164532 0.367091 0.069 Uiso 1 1 calc R U . . .
C23 C 0.60148(13) 0.01746(12) 0.28289(9) 0.0280(3) Uani 1 1 d . . . . .
H23A H 0.542194 -0.045596 0.287645 0.042 Uiso 1 1 calc R U . . .
H23B H 0.608859 0.032633 0.341679 0.042 Uiso 1 1 calc R U . . .
H23C H 0.680540 -0.009788 0.258717 0.042 Uiso 1 1 calc R U . . .
C24 C 0.55900(11) 0.13506(12) 0.22129(8) 0.0227(3) Uani 1 1 d . . . . .
C25 C 0.55756(12) 0.24960(12) 0.24500(8) 0.0238(3) Uani 1 1 d . . . . .
H25 H 0.582595 0.253864 0.300776 0.029 Uiso 1 1 calc R U . . .
C26 C 0.51926(12) 0.35789(12) 0.18657(8) 0.0224(3) Uani 1 1 d . . . . .
H26 H 0.518742 0.433151 0.204196 0.027 Uiso 1 1 calc R U . . .
C27 C 0.48177(11) 0.35559(11) 0.10235(8) 0.0193(2) Uani 1 1 d . . . . .
C28 C 0.48215(11) 0.23995(11) 0.07909(8) 0.0211(2) Uani 1 1 d . . . . .
H28 H 0.456227 0.235241 0.023659 0.025 Uiso 1 1 calc R U . . .
C29 C 0.52070(11) 0.13212(11) 0.13766(8) 0.0226(3) Uani 1 1 d . . . . .
H29 H 0.520820 0.056612 0.120430 0.027 Uiso 1 1 calc R U . . .
C30 C 0.44229(11) 0.47529(11) 0.03656(8) 0.0191(2) Uani 1 1 d . . . . .
C31 C 0.32987(11) 0.45129(11) -0.01192(8) 0.0213(2) Uani 1 1 d . . . . .
H31A H 0.309955 0.526092 -0.055938 0.026 Uiso 1 1 calc R U . . .
H31B H 0.352767 0.386211 -0.044347 0.026 Uiso 1 1 calc R U . . .
C32 C 0.21476(12) 0.41336(13) 0.05284(9) 0.0247(3) Uani 1 1 d . . . . .
H32A H 0.239548 0.357455 0.107374 0.030 Uiso 1 1 calc R U . . .
H32B H 0.175177 0.486599 0.069700 0.030 Uiso 1 1 calc R U . . .
C33 C 0.12206(12) 0.34970(13) 0.01098(9) 0.0266(3) Uani 1 1 d . . . . .
H33A H 0.102030 0.403367 -0.045786 0.032 Uiso 1 1 calc R U . . .
H33B H 0.160096 0.273549 -0.002084 0.032 Uiso 1 1 calc R U . . .
C34 C 0.00448(12) 0.31959(13) 0.07123(9) 0.0272(3) Uani 1 1 d . . . . .
C35 C -0.16678(14) 0.19058(15) 0.10802(11) 0.0379(3) Uani 1 1 d . . . . .
H35A H -0.158595 0.182969 0.171162 0.057 Uiso 1 1 calc R U . . .
H35B H -0.193726 0.113608 0.098555 0.057 Uiso 1 1 calc R U . . .
H35C H -0.226636 0.255622 0.088116 0.057 Uiso 1 1 calc R U . . .
C36 C 0.40343(11) 0.57405(11) 0.08533(8) 0.0208(2) Uani 1 1 d . . . . .
C37 C 0.36551(11) 0.65777(11) 0.11958(8) 0.0220(2) Uani 1 1 d . . . . .
C38 C 0.32265(11) 0.76516(11) 0.15402(8) 0.0214(2) Uani 1 1 d . . . . .
C39 C 0.30206(12) 0.87879(12) 0.09318(9) 0.0242(3) Uani 1 1 d . . . . .
H39 H 0.316222 0.883907 0.031309 0.029 Uiso 1 1 calc R U . . .
C40 C 0.26088(12) 0.98297(12) 0.12474(9) 0.0256(3) Uani 1 1 d . . . . .
H40 H 0.246528 1.057164 0.083592 0.031 Uiso 1 1 calc R U . . .
C41 C 0.24043(12) 0.97904(12) 0.21705(9) 0.0253(3) Uani 1 1 d . . . . .
C42 C 0.26095(12) 0.86617(13) 0.27691(9) 0.0259(3) Uani 1 1 d . . . . .
H42 H 0.247544 0.861693 0.338733 0.031 Uiso 1 1 calc R U . . .
C43 C 0.30096(12) 0.76009(12) 0.24655(9) 0.0247(3) Uani 1 1 d . . . . .
H43 H 0.313305 0.685606 0.287896 0.030 Uiso 1 1 calc R U . . .
C44 C 0.19967(15) 1.09490(13) 0.24990(10) 0.0338(3) Uani 1 1 d . . . . .
H44A H 0.177781 1.073627 0.313937 0.051 Uiso 1 1 calc R U . . .
H44B H 0.129105 1.132967 0.219835 0.051 Uiso 1 1 calc R U . . .
H44C H 0.266185 1.151908 0.236858 0.051 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 C12 1.2011(16) . ?
O2 C12 1.3370(17) . ?
O2 C13 1.4419(17) . ?
O3 C34 1.2044(17) . ?
O4 C34 1.3367(16) . ?
O4 C35 1.4449(17) . ?
C1 C2 1.506(2) . ?
C2 C3 1.3912(19) . ?
C2 C7 1.392(2) . ?
C3 C4 1.3917(19) . ?
C4 C5 1.3903(18) . ?
C5 C6 1.4017(17) . ?
C5 C8 1.5391(18) . ?
C6 C7 1.3878(19) . ?
C8 C14 1.4764(16) . ?
C8 C9 1.5481(16) . ?
C8 C8 1.632(2) 2_666 ?
C9 C10 1.5235(17) . ?
C10 C11 1.5297(18) . ?
C11 C12 1.5042(18) . ?
C14 C15 1.1956(18) . ?
C15 C16 1.4407(17) . ?
C16 C17 1.3936(18) . ?
C16 C21 1.3951(19) . ?
C17 C18 1.3883(19) . ?
C18 C19 1.383(2) . ?
C19 C20 1.395(2) . ?
C19 C22 1.5083(19) . ?
C20 C21 1.388(2) . ?
C23 C24 1.5024(17) . ?
C24 C29 1.3876(18) . ?
C24 C25 1.3923(18) . ?
C25 C26 1.3928(17) . ?
C26 C27 1.3911(18) . ?
C27 C28 1.4018(17) . ?
C27 C30 1.5389(16) . ?
C28 C29 1.3912(17) . ?
C30 C36 1.4757(17) . ?
C30 C31 1.5513(16) . ?
C30 C30 1.622(2) 2_665 ?
C31 C32 1.5282(16) . ?
C32 C33 1.5235(18) . ?
C33 C34 1.5023(18) . ?
C36 C37 1.1972(18) . ?
C37 C38 1.4406(17) . ?
C38 C43 1.3961(18) . ?
C38 C39 1.4055(17) . ?
C39 C40 1.3821(18) . ?
C40 C41 1.3943(19) . ?
C41 C42 1.3920(19) . ?
C41 C44 1.5074(18) . ?
C42 C43 1.3888(18) . ?

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
C12 O2 C13 117.10(11) . . ?
C34 O4 C35 115.21(11) . . ?
C3 C2 C7 117.39(13) . . ?
C3 C2 C1 121.28(13) . . ?
C7 C2 C1 121.33(13) . . ?
C2 C3 C4 120.92(13) . . ?
C5 C4 C3 121.99(12) . . ?
C4 C5 C6 116.90(12) . . ?
C4 C5 C8 121.39(11) . . ?
C6 C5 C8 121.66(11) . . ?
C7 C6 C5 121.06(12) . . ?
C6 C7 C2 121.74(12) . . ?
C14 C8 C5 110.02(10) . . ?
C14 C8 C9 108.47(10) . . ?
C5 C8 C9 111.99(10) . . ?
C14 C8 C8 107.18(12) . 2_666 ?
C5 C8 C8 109.82(12) . 2_666 ?
C9 C8 C8 109.24(12) . 2_666 ?
C10 C9 C8 115.34(10) . . ?
C9 C10 C11 109.73(11) . . ?
C12 C11 C10 115.33(11) . . ?
O1 C12 O2 123.39(13) . . ?
O1 C12 C11 125.46(13) . . ?
O2 C12 C11 111.13(11) . . ?
C15 C14 C8 177.33(13) . . ?
C14 C15 C16 176.22(13) . . ?
C17 C16 C21 118.13(12) . . ?
C17 C16 C15 121.51(12) . . ?
C21 C16 C15 120.35(12) . . ?
C18 C17 C16 120.54(13) . . ?
C19 C18 C17 121.64(13) . . ?
C18 C19 C20 117.84(13) . . ?
C18 C19 C22 120.69(15) . . ?
C20 C19 C22 121.47(15) . . ?
C21 C20 C19 121.02(14) . . ?
C20 C21 C16 120.82(13) . . ?
C29 C24 C25 117.89(11) . . ?
C29 C24 C23 120.22(12) . . ?
C25 C24 C23 121.89(12) . . ?
C24 C25 C26 121.11(12) . . ?
C27 C26 C25 121.23(12) . . ?
C26 C27 C28 117.50(11) . . ?
C26 C27 C30 121.50(11) . . ?
C28 C27 C30 121.00(11) . . ?
C29 C28 C27 121.00(11) . . ?
C24 C29 C28 121.26(12) . . ?
C36 C30 C27 110.90(10) . . ?
C36 C30 C31 107.20(10) . . ?
C27 C30 C31 110.21(9) . . ?
C36 C30 C30 108.06(11) . 2_665 ?
C27 C30 C30 109.89(11) . 2_665 ?
C31 C30 C30 110.54(12) . 2_665 ?
C32 C31 C30 113.16(10) . . ?
C33 C32 C31 112.08(11) . . ?
C34 C33 C32 112.85(11) . . ?
O3 C34 O4 122.71(13) . . ?
O3 C34 C33 125.29(13) . . ?
O4 C34 C33 111.98(12) . . ?
C37 C36 C30 174.68(13) . . ?
C36 C37 C38 175.43(13) . . ?
C43 C38 C39 118.65(11) . . ?
C43 C38 C37 121.92(11) . . ?
C39 C38 C37 119.43(11) . . ?
C40 C39 C38 120.40(12) . . ?
C39 C40 C41 121.31(12) . . ?
C42 C41 C40 117.97(12) . . ?
C42 C41 C44 121.68(12) . . ?
C40 C41 C44 120.34(12) . . ?
C43 C42 C41 121.61(12) . . ?
C42 C43 C38 120.06(12) . . ?

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.043

