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

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

data_200906e
_database_code_depnum_ccdc_archive 'CCDC 2039963'
loop_
_audit_author_name
_audit_author_address
'Ran Song'
;Qingdao University of Science and Technology
China
;
_audit_update_record             
;
2020-10-22 deposited with the CCDC.	2021-09-21 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         ?
_chemical_formula_sum            'C13.50 H16 O1.50'
_chemical_formula_weight         202.26

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      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                   10.835(17)
_cell_length_b                   10.925(17)
_cell_length_c                   10.995(17)
_cell_angle_alpha                84.933(17)
_cell_angle_beta                 64.499(17)
_cell_angle_gamma                79.764(19)
_cell_volume                     1156(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1897
_cell_measurement_theta_min      2.235
_cell_measurement_theta_max      27.245

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9689
_exptl_absorpt_correction_T_max  0.9724
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5822
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.052
_diffrn_reflns_theta_max         25.015
_diffrn_reflns_theta_full        25.015
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4006
_reflns_number_gt                2636
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0798P)²] 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       0.046(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4006
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1576
_refine_ls_wR_factor_gt          0.1433
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.44536(17) -0.09070(14) 0.29586(14) 0.0505(5) Uani 1 1 d . . . . .
H1 H 0.457668 -0.164638 0.315459 0.076 Uiso 1 1 calc R U . . .
O2 O 0.46525(17) 0.14130(16) -0.02093(15) 0.0550(5) Uani 1 1 d . . . . .
H2 H 0.487651 0.111786 -0.094871 0.066 Uiso 1 1 calc R U . . .
O3 O 0.46732(16) 0.66813(13) 0.23541(15) 0.0479(4) Uani 1 1 d . . . . .
H3 H 0.483250 0.698051 0.160038 0.057 Uiso 1 1 calc R U . . .
C1 C 0.3892(2) 0.16328(19) 0.25485(19) 0.0320(5) Uani 1 1 d . . . . .
H1A H 0.479681 0.117999 0.196328 0.038 Uiso 1 1 calc R U . . .
C2 C 0.3534(2) 0.10738(19) 0.39605(19) 0.0328(5) Uani 1 1 d . . . . .
C3 C 0.3813(2) -0.02153(19) 0.4122(2) 0.0345(5) Uani 1 1 d . . . . .
C4 C 0.3479(2) -0.0770(2) 0.5381(2) 0.0429(6) Uani 1 1 d . . . . .
H4 H 0.368664 -0.162773 0.546145 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2833(2) -0.0041(2) 0.6522(2) 0.0466(6) Uani 1 1 d . . . . .
H5 H 0.259760 -0.041006 0.737169 0.056 Uiso 1 1 calc R U . . .
C6 C 0.2541(2) 0.1233(2) 0.6398(2) 0.0488(6) Uani 1 1 d . . . . .
H6 H 0.210507 0.172436 0.716217 0.059 Uiso 1 1 calc R U . . .
C7 C 0.2899(2) 0.1777(2) 0.5128(2) 0.0423(6) Uani 1 1 d . . . . .
H7 H 0.271045 0.263794 0.505449 0.051 Uiso 1 1 calc R U . . .
C8 C 0.2874(2) 0.13871(19) 0.2010(2) 0.0348(5) Uani 1 1 d . . . . .
C9 C 0.3307(2) 0.1252(2) 0.0630(2) 0.0421(6) Uani 1 1 d . . . . .
C10 C 0.2419(3) 0.0986(2) 0.0129(3) 0.0613(8) Uani 1 1 d . . . . .
H10 H 0.272419 0.090306 -0.079412 0.074 Uiso 1 1 calc R U . . .
C11 C 0.1083(3) 0.0844(3) 0.0988(3) 0.0713(9) Uani 1 1 d . . . . .
H11 H 0.049120 0.065277 0.064678 0.086 Uiso 1 1 calc R U . . .
C12 C 0.0618(3) 0.0985(3) 0.2361(3) 0.0687(8) Uani 1 1 d . . . . .
H12 H -0.029051 0.090526 0.294405 0.082 Uiso 1 1 calc R U . . .
C13 C 0.1517(2) 0.1245(2) 0.2861(2) 0.0504(6) Uani 1 1 d . . . . .
H13 H 0.120590 0.132734 0.378496 0.061 Uiso 1 1 calc R U . . .
C14 C 0.4462(2) 0.54442(19) 0.2390(2) 0.0365(5) Uani 1 1 d . . . . .
C15 C 0.3161(2) 0.52228(19) 0.2574(2) 0.0363(5) Uani 1 1 d . . . . .
C16 C 0.3011(2) 0.39693(19) 0.2594(2) 0.0370(5) Uani 1 1 d . . . . .
H16 H 0.216693 0.378278 0.269537 0.044 Uiso 1 1 calc R U . . .
C17 C 0.4071(2) 0.30011(18) 0.24697(19) 0.0322(5) Uani 1 1 d . . . . .
C18 C 0.5328(2) 0.3280(2) 0.23200(19) 0.0357(5) Uani 1 1 d . . . . .
H18 H 0.603940 0.262882 0.223804 0.043 Uiso 1 1 calc R U . . .
C19 C 0.5570(2) 0.45003(19) 0.22872(19) 0.0346(5) Uani 1 1 d . . . . .
C20 C 0.1942(2) 0.6276(2) 0.2775(2) 0.0435(6) Uani 1 1 d . . . . .
C21 C 0.0637(2) 0.5777(2) 0.2946(3) 0.0610(7) Uani 1 1 d . . . . .
H21A H 0.082941 0.532941 0.215507 0.092 Uiso 1 1 calc R U . . .
H21B H -0.009753 0.646009 0.307167 0.092 Uiso 1 1 calc R U . . .
H21C H 0.036372 0.523026 0.371754 0.092 Uiso 1 1 calc R U . . .
C22 C 0.2297(3) 0.7188(3) 0.1546(3) 0.0655(8) Uani 1 1 d . . . . .
H22A H 0.295321 0.767733 0.154135 0.098 Uiso 1 1 calc R U . . .
H22B H 0.146970 0.772698 0.161009 0.098 Uiso 1 1 calc R U . . .
H22C H 0.268890 0.672284 0.072914 0.098 Uiso 1 1 calc R U . . .
C23 C 0.1546(3) 0.7006(3) 0.4066(3) 0.0674(8) Uani 1 1 d . . . . .
H23A H 0.125889 0.645615 0.483482 0.101 Uiso 1 1 calc R U . . .
H23B H 0.080163 0.767087 0.416454 0.101 Uiso 1 1 calc R U . . .
H23C H 0.233299 0.734264 0.400142 0.101 Uiso 1 1 calc R U . . .
C24 C 0.6970(2) 0.4775(2) 0.2163(2) 0.0438(6) Uani 1 1 d . . . . .
C25 C 0.7630(3) 0.5634(3) 0.0943(3) 0.0676(8) Uani 1 1 d . . . . .
H25A H 0.711852 0.646083 0.112806 0.101 Uiso 1 1 calc R U . . .
H25B H 0.761187 0.532762 0.016062 0.101 Uiso 1 1 calc R U . . .
H25C H 0.857131 0.564900 0.078325 0.101 Uiso 1 1 calc R U . . .
C26 C 0.8024(3) 0.3586(2) 0.1976(3) 0.0634(8) Uani 1 1 d . . . . .
H26A H 0.888164 0.379729 0.188826 0.095 Uiso 1 1 calc R U . . .
H26B H 0.817566 0.317013 0.117874 0.095 Uiso 1 1 calc R U . . .
H26C H 0.767394 0.304571 0.274480 0.095 Uiso 1 1 calc R U . . .
C27 C 0.6734(3) 0.5388(3) 0.3474(3) 0.0689(8) Uani 1 1 d . . . . .
H27A H 0.609835 0.615104 0.360601 0.103 Uiso 1 1 calc R U . . .
H27B H 0.759961 0.555974 0.340848 0.103 Uiso 1 1 calc R U . . .
H27C H 0.635752 0.483442 0.422403 0.103 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 C3 1.382(3) . ?
O1 H1 0.8200 . ?
O2 C9 1.383(3) . ?
O2 H2 0.8200 . ?
O3 C14 1.405(3) . ?
O3 H3 0.8200 . ?
C1 C2 1.527(3) . ?
C1 C8 1.528(3) . ?
C1 C17 1.532(4) . ?
C1 H1A 0.9800 . ?
C2 C7 1.392(3) . ?
C2 C3 1.399(4) . ?
C3 C4 1.383(3) . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.390(4) . ?
C8 C9 1.396(4) . ?
C9 C10 1.377(4) . ?
C10 C11 1.374(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.397(4) . ?
C14 C19 1.408(3) . ?
C15 C16 1.405(4) . ?
C15 C20 1.540(4) . ?
C16 C17 1.384(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(3) . ?
C18 C19 1.398(4) . ?
C18 H18 0.9300 . ?
C19 C24 1.544(4) . ?
C20 C21 1.536(4) . ?
C20 C23 1.545(4) . ?
C20 C22 1.554(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C26 1.534(4) . ?
C24 C25 1.543(4) . ?
C24 C27 1.545(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 109.5 . . ?
C9 O2 H2 109.5 . . ?
C14 O3 H3 109.5 . . ?
C2 C1 C8 110.87(18) . . ?
C2 C1 C17 112.45(16) . . ?
C8 C1 C17 113.98(16) . . ?
C2 C1 H1A 106.3 . . ?
C8 C1 H1A 106.3 . . ?
C17 C1 H1A 106.3 . . ?
C7 C2 C3 116.9(2) . . ?
C7 C2 C1 123.5(2) . . ?
C3 C2 C1 119.51(17) . . ?
O1 C3 C4 121.6(2) . . ?
O1 C3 C2 116.64(19) . . ?
C4 C3 C2 121.75(19) . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 119.7(2) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C2 122.0(2) . . ?
C6 C7 H7 119.0 . . ?
C2 C7 H7 119.0 . . ?
C13 C8 C9 117.7(2) . . ?
C13 C8 C1 122.1(2) . . ?
C9 C8 C1 120.2(2) . . ?
C10 C9 O2 121.7(2) . . ?
C10 C9 C8 121.1(2) . . ?
O2 C9 C8 117.2(2) . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 119.5(3) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C8 121.4(3) . . ?
C12 C13 H13 119.3 . . ?
C8 C13 H13 119.3 . . ?
C15 C14 O3 118.51(19) . . ?
C15 C14 C19 124.1(2) . . ?
O3 C14 C19 117.4(2) . . ?
C14 C15 C16 116.06(19) . . ?
C14 C15 C20 122.7(2) . . ?
C16 C15 C20 121.2(2) . . ?
C17 C16 C15 122.5(2) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C16 C17 C18 118.7(2) . . ?
C16 C17 C1 122.6(2) . . ?
C18 C17 C1 118.66(18) . . ?
C17 C18 C19 122.7(2) . . ?
C17 C18 H18 118.7 . . ?
C19 C18 H18 118.7 . . ?
C18 C19 C14 115.9(2) . . ?
C18 C19 C24 121.24(19) . . ?
C14 C19 C24 122.8(2) . . ?
C21 C20 C15 112.0(2) . . ?
C21 C20 C23 106.5(2) . . ?
C15 C20 C23 110.5(2) . . ?
C21 C20 C22 106.9(2) . . ?
C15 C20 C22 111.3(2) . . ?
C23 C20 C22 109.4(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C26 C24 C25 106.9(2) . . ?
C26 C24 C19 112.1(2) . . ?
C25 C24 C19 111.60(19) . . ?
C26 C24 C27 107.4(2) . . ?
C25 C24 C27 109.9(2) . . ?
C19 C24 C27 108.82(19) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C8 C1 C2 C7 -104.4(2) . . . . ?
C17 C1 C2 C7 24.5(3) . . . . ?
C8 C1 C2 C3 73.9(2) . . . . ?
C17 C1 C2 C3 -157.23(19) . . . . ?
C7 C2 C3 O1 -179.46(18) . . . . ?
C1 C2 C3 O1 2.2(3) . . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
C1 C2 C3 C4 -178.47(18) . . . . ?
O1 C3 C4 C5 -179.82(19) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C5 C6 C7 C2 1.0(3) . . . . ?
C3 C2 C7 C6 -0.8(3) . . . . ?
C1 C2 C7 C6 177.5(2) . . . . ?
C2 C1 C8 C13 28.4(3) . . . . ?
C17 C1 C8 C13 -99.7(2) . . . . ?
C2 C1 C8 C9 -149.2(2) . . . . ?
C17 C1 C8 C9 82.7(2) . . . . ?
C13 C8 C9 C10 0.0(3) . . . . ?
C1 C8 C9 C10 177.7(2) . . . . ?
C13 C8 C9 O2 179.1(2) . . . . ?
C1 C8 C9 O2 -3.2(3) . . . . ?
O2 C9 C10 C11 -179.3(2) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 C13 -1.3(5) . . . . ?
C11 C12 C13 C8 1.0(4) . . . . ?
C9 C8 C13 C12 -0.3(4) . . . . ?
C1 C8 C13 C12 -178.0(2) . . . . ?
O3 C14 C15 C16 179.67(17) . . . . ?
C19 C14 C15 C16 -2.8(3) . . . . ?
O3 C14 C15 C20 -1.6(3) . . . . ?
C19 C14 C15 C20 175.89(19) . . . . ?
C14 C15 C16 C17 1.4(3) . . . . ?
C20 C15 C16 C17 -177.39(18) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C15 C16 C17 C1 177.47(18) . . . . ?
C2 C1 C17 C16 -95.4(2) . . . . ?
C8 C1 C17 C16 31.9(3) . . . . ?
C2 C1 C17 C18 82.1(2) . . . . ?
C8 C1 C17 C18 -150.64(19) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C1 C17 C18 C19 -177.66(18) . . . . ?
C17 C18 C19 C14 -1.2(3) . . . . ?
C17 C18 C19 C24 178.10(18) . . . . ?
C15 C14 C19 C18 2.8(3) . . . . ?
O3 C14 C19 C18 -179.72(17) . . . . ?
C15 C14 C19 C24 -176.51(19) . . . . ?
O3 C14 C19 C24 1.0(3) . . . . ?
C14 C15 C20 C21 179.7(2) . . . . ?
C16 C15 C20 C21 -1.7(3) . . . . ?
C14 C15 C20 C23 -61.7(3) . . . . ?
C16 C15 C20 C23 116.9(2) . . . . ?
C14 C15 C20 C22 60.0(3) . . . . ?
C16 C15 C20 C22 -121.3(2) . . . . ?
C18 C19 C24 C26 4.4(3) . . . . ?
C14 C19 C24 C26 -176.4(2) . . . . ?
C18 C19 C24 C25 124.3(2) . . . . ?
C14 C19 C24 C25 -56.5(3) . . . . ?
C18 C19 C24 C27 -114.2(2) . . . . ?
C14 C19 C24 C27 65.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 0.82 2.06 2.719(5) 136.6 1_545 yes
O2 H2 O1 0.82 2.03 2.822(5) 163.0 2_655 yes
O3 H3 O2 0.82 2.21 2.936(4) 148.2 2_665 yes
O1 H1 O3 0.82 2.06 2.719(5) 136.6 1_545 yes

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_mx9380_sq
_database_code_depnum_ccdc_archive 'CCDC 2085323'
loop_
_audit_author_name
_audit_author_address
zhuocaiqi
;Qingdao University of Science and Technology
China
;
_audit_update_record             
;
2021-05-23 deposited with the CCDC.	2021-09-21 downloaded from the CCDC.
;
_audit_creation_date             2021-05-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H52 O4'
_chemical_formula_sum            'C42 H52 O4'
_chemical_formula_weight         620.83
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.5033(6)
_cell_length_b                   31.9324(10)
_cell_length_c                   12.5127(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.215(4)
_cell_angle_gamma                90
_cell_volume                     4745.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12267
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      30.5760
_cell_measurement_theta_min      1.8420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
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    0.869
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            43438
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.081
_diffrn_reflns_theta_min         1.828
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     13.00  39.00   0.50   10.00    --    5.00  45.00  90.00   52
  2  ω    -81.00 -56.00   0.50   10.00    --  -11.60  45.00 133.78   50
  3  ω    -44.00  72.00   0.50   10.00    --  -11.60  45.00 133.78  232
  4  ω    -34.00  66.00   0.50   10.00    --  -11.60  45.00  30.00  200
  5  ω   -100.00 -56.00   0.50   10.00    --  -11.60  45.00  30.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0188300000
_diffrn_orient_matrix_UB_12      0.0210712000
_diffrn_orient_matrix_UB_13      0.0081932000
_diffrn_orient_matrix_UB_21      0.0519060000
_diffrn_orient_matrix_UB_22      -0.0067805000
_diffrn_orient_matrix_UB_23      0.0382766000
_diffrn_orient_matrix_UB_31      0.0227830000
_diffrn_orient_matrix_UB_32      -0.0018666000
_diffrn_orient_matrix_UB_33      -0.0450338000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8571
_reflns_number_total             12726
_reflns_odcompleteness_completeness 98.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         12726
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.105
_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)+(0.0651P)²+0.1361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1334
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H37A-H4
 2.1 with sigma of 0.01
3.a Riding coordinates:
 O4(H4)
3.b Ternary CH refined with riding coordinates:
 C7(H7), C9(H9)
3.c Me refined with riding coordinates:
 C37(H37A,H37B,H37C)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4A), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C30(H30), C34(H34)
3.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C36(H36A,H36B,H36C), C38(H38A,
 H38B,H38C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
3.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.48063(7) 0.43665(2) 0.52994(6) 0.03315(18) Uani 1 1 d . . . . .
O2 O 0.59165(8) 0.29619(3) 0.79789(7) 0.0490(2) Uani 1 1 d . . . . .
H2 H 0.616841 0.275237 0.835158 0.074 Uiso 1 1 calc R U . . .
O3 O 0.20815(7) 0.27200(3) 0.42135(7) 0.0484(2) Uani 1 1 d . . . . .
O4 O 0.43662(9) 0.35869(3) 0.05328(6) 0.0561(3) Uani 1 1 d . . . . .
H4 H 0.377504 0.351015 0.007225 0.084 Uiso 1 1 d DR U . . .
C1 C 0.48907(9) 0.41597(3) 0.71936(8) 0.0325(2) Uani 1 1 d . . . . .
C2 C 0.49350(12) 0.42971(4) 0.82619(9) 0.0480(3) Uani 1 1 d . . . . .
H2A H 0.496404 0.410100 0.881965 0.058 Uiso 1 1 calc R U . . .
C3 C 0.49367(15) 0.47165(4) 0.85109(11) 0.0642(4) Uani 1 1 d . . . . .
H3 H 0.495915 0.480120 0.922874 0.077 Uiso 1 1 calc R U . . .
C4 C 0.49050(14) 0.50113(4) 0.76975(11) 0.0596(4) Uani 1 1 d . . . . .
H4A H 0.490648 0.529492 0.786661 0.072 Uiso 1 1 calc R U . . .
C5 C 0.48713(12) 0.48864(3) 0.66365(10) 0.0447(3) Uani 1 1 d . . . . .
H5 H 0.485387 0.508463 0.608688 0.054 Uiso 1 1 calc R U . . .
C6 C 0.48636(10) 0.44635(3) 0.63915(8) 0.0329(2) Uani 1 1 d . . . . .
C7 C 0.49214(9) 0.36988(3) 0.69282(8) 0.0288(2) Uani 1 1 d . . . . .
H7 H 0.571636 0.361672 0.716117 0.035 Uiso 1 1 calc R U . . .
C8 C 0.44478(8) 0.36292(3) 0.56166(8) 0.0264(2) Uani 1 1 d . . . . .
C9 C 0.51063(9) 0.39480(3) 0.51134(8) 0.0280(2) Uani 1 1 d . . . . .
H9 H 0.591188 0.391196 0.550765 0.034 Uiso 1 1 calc R U . . .
C10 C 0.43463(9) 0.34154(3) 0.75496(8) 0.0299(2) Uani 1 1 d . . . . .
C11 C 0.48630(10) 0.30444(3) 0.80349(8) 0.0353(2) Uani 1 1 d . . . . .
C12 C 0.43167(12) 0.27714(4) 0.85492(9) 0.0438(3) Uani 1 1 d . . . . .
H12 H 0.466812 0.252396 0.886518 0.053 Uiso 1 1 calc R U . . .
C13 C 0.32611(12) 0.28632(4) 0.85958(9) 0.0447(3) Uani 1 1 d . . . . .
H13 H 0.289880 0.267779 0.894116 0.054 Uiso 1 1 calc R U . . .
C14 C 0.27360(11) 0.32295(4) 0.81319(9) 0.0397(3) Uani 1 1 d . . . . .
H14 H 0.202029 0.329268 0.816316 0.048 Uiso 1 1 calc R U . . .
C15 C 0.32819(10) 0.35018(3) 0.76206(8) 0.0333(2) Uani 1 1 d . . . . .
H15 H 0.292724 0.375002 0.731510 0.040 Uiso 1 1 calc R U . . .
C16 C 0.47436(9) 0.32007(3) 0.53582(8) 0.0284(2) Uani 1 1 d . . . . .
H16 H 0.550455 0.313404 0.555392 0.034 Uiso 1 1 calc R U . . .
C17 C 0.40075(9) 0.29022(3) 0.48673(8) 0.0308(2) Uani 1 1 d . . . . .
C18 C 0.27903(9) 0.29958(3) 0.45819(8) 0.0328(2) Uani 1 1 d . . . . .
C19 C 0.24320(9) 0.34289(3) 0.47382(8) 0.0296(2) Uani 1 1 d . . . . .
C20 C 0.32250(9) 0.37134(3) 0.51956(8) 0.0278(2) Uani 1 1 d . . . . .
H20 H 0.298922 0.398622 0.525402 0.033 Uiso 1 1 calc R U . . .
C21 C 0.43815(11) 0.24688(3) 0.45994(11) 0.0426(3) Uani 1 1 d . . . . .
C22 C 0.56614(13) 0.24418(4) 0.49287(14) 0.0608(4) Uani 1 1 d . . . . .
H22A H 0.593553 0.265561 0.454180 0.091 Uiso 1 1 calc R U . . .
H22B H 0.587406 0.217169 0.472552 0.091 Uiso 1 1 calc R U . . .
H22C H 0.598039 0.248114 0.572612 0.091 Uiso 1 1 calc R U . . .
C23 C 0.39785(14) 0.21314(4) 0.52544(13) 0.0618(4) Uani 1 1 d . . . . .
H23A H 0.425269 0.219378 0.604394 0.093 Uiso 1 1 calc R U . . .
H23B H 0.425968 0.186338 0.511947 0.093 Uiso 1 1 calc R U . . .
H23C H 0.317037 0.212544 0.501025 0.093 Uiso 1 1 calc R U . . .
C24 C 0.39015(14) 0.23901(5) 0.33293(12) 0.0615(4) Uani 1 1 d . . . . .
H24A H 0.309414 0.238415 0.311176 0.092 Uiso 1 1 calc R U . . .
H24B H 0.417274 0.212647 0.315015 0.092 Uiso 1 1 calc R U . . .
H24C H 0.413704 0.261043 0.293123 0.092 Uiso 1 1 calc R U . . .
C25 C 0.11731(9) 0.35280(4) 0.43906(9) 0.0385(3) Uani 1 1 d . . . . .
C26 C 0.06265(11) 0.32788(4) 0.51356(10) 0.0467(3) Uani 1 1 d . . . . .
H26A H 0.078894 0.298632 0.509868 0.070 Uiso 1 1 calc R U . . .
H26B H -0.017368 0.332092 0.487340 0.070 Uiso 1 1 calc R U . . .
H26C H 0.092337 0.337372 0.589959 0.070 Uiso 1 1 calc R U . . .
C27 C 0.06070(11) 0.34223(5) 0.31437(10) 0.0521(3) Uani 1 1 d . . . . .
H27A H 0.100277 0.355947 0.269716 0.078 Uiso 1 1 calc R U . . .
H27B H -0.016043 0.351656 0.291582 0.078 Uiso 1 1 calc R U . . .
H27C H 0.062495 0.312491 0.303876 0.078 Uiso 1 1 calc R U . . .
C28 C 0.09752(11) 0.39911(4) 0.45545(13) 0.0575(4) Uani 1 1 d . . . . .
H28A H 0.130195 0.406295 0.533385 0.086 Uiso 1 1 calc R U . . .
H28B H 0.018073 0.404601 0.432393 0.086 Uiso 1 1 calc R U . . .
H28C H 0.131818 0.415596 0.410884 0.086 Uiso 1 1 calc R U . . .
C29 C 0.49180(9) 0.38883(3) 0.38786(8) 0.0278(2) Uani 1 1 d . . . . .
C30 C 0.39435(9) 0.40200(3) 0.30680(8) 0.0297(2) Uani 1 1 d . . . . .
H30 H 0.341435 0.417201 0.328968 0.036 Uiso 1 1 calc R U . . .
C31 C 0.37322(9) 0.39317(3) 0.19308(8) 0.0322(2) Uani 1 1 d . . . . .
C32 C 0.45451(10) 0.36971(3) 0.16363(8) 0.0345(2) Uani 1 1 d . . . . .
C33 C 0.55656(10) 0.35740(3) 0.24237(9) 0.0332(2) Uani 1 1 d . . . . .
C34 C 0.57165(9) 0.36759(3) 0.35370(8) 0.0310(2) Uani 1 1 d . . . . .
H34 H 0.638478 0.359795 0.407808 0.037 Uiso 1 1 calc R U . . .
C35 C 0.26330(10) 0.40761(4) 0.10495(9) 0.0405(3) Uani 1 1 d . . . . .
C36 C 0.19633(11) 0.43675(4) 0.15667(10) 0.0517(3) Uani 1 1 d . . . . .
H36A H 0.175926 0.422115 0.214464 0.078 Uiso 1 1 calc R U . . .
H36B H 0.129410 0.445793 0.099455 0.078 Uiso 1 1 calc R U . . .
H36C H 0.241480 0.460676 0.188669 0.078 Uiso 1 1 calc R U . . .
C37 C 0.18978(12) 0.36920(5) 0.05755(11) 0.0538(3) Uani 1 1 d . . . . .
H37A H 0.230363 0.350374 0.024471 0.081 Uiso 1 1 calc DR U . . .
H37B H 0.171128 0.355190 0.117254 0.081 Uiso 1 1 calc R U . . .
H37C H 0.121914 0.378043 0.001317 0.081 Uiso 1 1 calc R U . . .
C38 C 0.28683(12) 0.43234(5) 0.00872(10) 0.0547(4) Uani 1 1 d . . . . .
H38A H 0.335584 0.455526 0.039528 0.082 Uiso 1 1 calc R U . . .
H38B H 0.217145 0.442584 -0.041824 0.082 Uiso 1 1 calc R U . . .
H38C H 0.322383 0.414288 -0.031411 0.082 Uiso 1 1 calc R U . . .
C39 C 0.64767(11) 0.33364(4) 0.20785(10) 0.0415(3) Uani 1 1 d . . . . .
C40 C 0.60584(12) 0.29003(4) 0.16233(12) 0.0541(3) Uani 1 1 d . . . . .
H40A H 0.589755 0.273935 0.220279 0.081 Uiso 1 1 calc R U . . .
H40B H 0.662907 0.276129 0.138991 0.081 Uiso 1 1 calc R U . . .
H40C H 0.538683 0.292722 0.099216 0.081 Uiso 1 1 calc R U . . .
C41 C 0.68359(15) 0.35887(5) 0.11966(13) 0.0651(4) Uani 1 1 d . . . . .
H41A H 0.622534 0.359689 0.050355 0.098 Uiso 1 1 calc R U . . .
H41B H 0.747709 0.345740 0.107145 0.098 Uiso 1 1 calc R U . . .
H41C H 0.702883 0.386894 0.146586 0.098 Uiso 1 1 calc R U . . .
C42 C 0.75328(11) 0.32733(4) 0.30813(11) 0.0498(3) Uani 1 1 d . . . . .
H42A H 0.782905 0.354091 0.338137 0.075 Uiso 1 1 calc R U . . .
H42B H 0.808665 0.312483 0.284345 0.075 Uiso 1 1 calc R U . . .
H42C H 0.734802 0.311433 0.365072 0.075 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 C6 1.3810(12) . ?
O1 C9 1.4267(12) . ?
O2 H2 0.8200 . ?
O2 C11 1.3665(14) . ?
O3 C18 1.2320(12) . ?
O4 H4 0.8199 . ?
O4 C32 1.3739(12) . ?
C1 C2 1.3916(15) . ?
C1 C6 1.3887(15) . ?
C1 C7 1.5118(14) . ?
C2 H2A 0.9300 . ?
C2 C3 1.3746(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.3779(19) . ?
C4 H4A 0.9300 . ?
C4 C5 1.3742(16) . ?
C5 H5 0.9300 . ?
C5 C6 1.3840(15) . ?
C7 H7 0.9800 . ?
C7 C8 1.5766(13) . ?
C7 C10 1.5132(14) . ?
C8 C9 1.5603(14) . ?
C8 C16 1.4793(13) . ?
C8 C20 1.4778(14) . ?
C9 H9 0.9800 . ?
C9 C29 1.5005(13) . ?
C10 C11 1.3944(14) . ?
C10 C15 1.3889(16) . ?
C11 C12 1.3841(16) . ?
C12 H12 0.9300 . ?
C12 C13 1.3709(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.3777(17) . ?
C14 H14 0.9300 . ?
C14 C15 1.3800(16) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.3341(14) . ?
C17 C18 1.4809(16) . ?
C17 C21 1.5310(15) . ?
C18 C19 1.4853(15) . ?
C19 C20 1.3346(14) . ?
C19 C25 1.5294(15) . ?
C20 H20 0.9300 . ?
C21 C22 1.5251(19) . ?
C21 C23 1.5313(18) . ?
C21 C24 1.5338(19) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.5387(17) . ?
C25 C27 1.5358(16) . ?
C25 C28 1.5235(18) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.3849(14) . ?
C29 C34 1.3806(15) . ?
C30 H30 0.9300 . ?
C30 C31 1.3926(14) . ?
C31 C32 1.4014(16) . ?
C31 C35 1.5396(15) . ?
C32 C33 1.4027(16) . ?
C33 C34 1.3849(14) . ?
C33 C39 1.5386(16) . ?
C34 H34 0.9300 . ?
C35 C36 1.5246(18) . ?
C35 C37 1.5363(18) . ?
C35 C38 1.5431(17) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.5332(17) . ?
C39 C41 1.5422(18) . ?
C39 C42 1.5242(18) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C9 115.89(7) . . ?
C11 O2 H2 109.5 . . ?
C32 O4 H4 127.6 . . ?
C2 C1 C7 121.47(9) . . ?
C6 C1 C2 117.28(10) . . ?
C6 C1 C7 121.20(9) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 C1 121.46(11) . . ?
C3 C2 H2A 119.3 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.02(11) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 C3 120.03(11) . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.55(11) . . ?
C6 C5 H5 120.2 . . ?
O1 C6 C1 122.70(9) . . ?
O1 C6 C5 115.64(9) . . ?
C5 C6 C1 121.65(10) . . ?
C1 C7 H7 106.7 . . ?
C1 C7 C8 109.80(8) . . ?
C1 C7 C10 114.86(9) . . ?
C8 C7 H7 106.7 . . ?
C10 C7 H7 106.7 . . ?
C10 C7 C8 111.49(8) . . ?
C9 C8 C7 104.73(7) . . ?
C16 C8 C7 108.64(8) . . ?
C16 C8 C9 108.40(8) . . ?
C20 C8 C7 110.83(8) . . ?
C20 C8 C9 110.81(8) . . ?
C20 C8 C16 113.06(8) . . ?
O1 C9 C8 110.26(8) . . ?
O1 C9 H9 108.0 . . ?
O1 C9 C29 108.81(8) . . ?
C8 C9 H9 108.0 . . ?
C29 C9 C8 113.57(8) . . ?
C29 C9 H9 108.0 . . ?
C11 C10 C7 120.12(10) . . ?
C15 C10 C7 122.20(9) . . ?
C15 C10 C11 117.62(10) . . ?
O2 C11 C10 117.67(10) . . ?
O2 C11 C12 121.73(10) . . ?
C12 C11 C10 120.60(11) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.44(11) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.14(11) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.39(12) . . ?
C15 C14 H14 120.3 . . ?
C10 C15 H15 119.1 . . ?
C14 C15 C10 121.82(10) . . ?
C14 C15 H15 119.1 . . ?
C8 C16 H16 117.3 . . ?
C17 C16 C8 125.31(10) . . ?
C17 C16 H16 117.3 . . ?
C16 C17 C18 118.42(9) . . ?
C16 C17 C21 122.19(10) . . ?
C18 C17 C21 119.39(9) . . ?
O3 C18 C17 120.72(10) . . ?
O3 C18 C19 120.23(10) . . ?
C17 C18 C19 119.05(9) . . ?
C18 C19 C25 118.77(9) . . ?
C20 C19 C18 118.43(10) . . ?
C20 C19 C25 122.79(10) . . ?
C8 C20 H20 117.4 . . ?
C19 C20 C8 125.19(9) . . ?
C19 C20 H20 117.4 . . ?
C17 C21 C23 110.16(10) . . ?
C17 C21 C24 109.12(10) . . ?
C22 C21 C17 111.01(10) . . ?
C22 C21 C23 107.98(11) . . ?
C22 C21 C24 107.96(11) . . ?
C23 C21 C24 110.58(11) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C25 C26 109.46(9) . . ?
C19 C25 C27 110.48(10) . . ?
C27 C25 C26 110.54(10) . . ?
C28 C25 C19 111.02(10) . . ?
C28 C25 C26 107.39(11) . . ?
C28 C25 C27 107.90(11) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 C9 122.31(9) . . ?
C34 C29 C9 119.03(9) . . ?
C34 C29 C30 118.57(9) . . ?
C29 C30 H30 119.0 . . ?
C29 C30 C31 121.96(10) . . ?
C31 C30 H30 119.0 . . ?
C30 C31 C32 117.09(9) . . ?
C30 C31 C35 120.86(10) . . ?
C32 C31 C35 122.02(9) . . ?
O4 C32 C31 119.84(10) . . ?
O4 C32 C33 117.43(10) . . ?
C31 C32 C33 122.72(9) . . ?
C32 C33 C39 122.13(9) . . ?
C34 C33 C32 116.65(10) . . ?
C34 C33 C39 121.22(10) . . ?
C29 C34 C33 122.86(10) . . ?
C29 C34 H34 118.6 . . ?
C33 C34 H34 118.6 . . ?
C31 C35 C38 111.53(10) . . ?
C36 C35 C31 111.38(9) . . ?
C36 C35 C37 108.02(11) . . ?
C36 C35 C38 106.44(10) . . ?
C37 C35 C31 109.26(10) . . ?
C37 C35 C38 110.14(10) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C33 C39 C41 110.49(10) . . ?
C40 C39 C33 110.83(10) . . ?
C40 C39 C41 110.52(11) . . ?
C42 C39 C33 111.16(9) . . ?
C42 C39 C40 107.03(10) . . ?
C42 C39 C41 106.68(11) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 1.99 2.8005(11) 168.1 4_666 yes

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 C9 C29 C30 -46.23(12) . . . . ?
O1 C9 C29 C34 137.13(9) . . . . ?
O2 C11 C12 C13 179.79(10) . . . . ?
O3 C18 C19 C20 176.45(10) . . . . ?
O3 C18 C19 C25 -2.38(15) . . . . ?
O4 C32 C33 C34 -177.98(9) . . . . ?
O4 C32 C33 C39 1.87(16) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C1 C7 C8 C9 50.43(10) . . . . ?
C1 C7 C8 C16 166.10(9) . . . . ?
C1 C7 C8 C20 -69.11(10) . . . . ?
C1 C7 C10 C11 -135.58(10) . . . . ?
C1 C7 C10 C15 47.16(13) . . . . ?
C2 C1 C6 O1 -179.24(11) . . . . ?
C2 C1 C6 C5 -0.49(18) . . . . ?
C2 C1 C7 C8 160.56(11) . . . . ?
C2 C1 C7 C10 33.97(15) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 O1 178.75(12) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C6 O1 C9 C8 50.80(11) . . . . ?
C6 O1 C9 C29 175.97(8) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C6 C1 C7 C8 -22.12(14) . . . . ?
C6 C1 C7 C10 -148.70(10) . . . . ?
C7 C1 C2 C3 178.28(13) . . . . ?
C7 C1 C6 O1 3.32(17) . . . . ?
C7 C1 C6 C5 -177.92(11) . . . . ?
C7 C8 C9 O1 -66.80(9) . . . . ?
C7 C8 C9 C29 170.79(8) . . . . ?
C7 C8 C16 C17 119.08(11) . . . . ?
C7 C8 C20 C19 -115.13(10) . . . . ?
C7 C10 C11 O2 3.49(14) . . . . ?
C7 C10 C11 C12 -176.29(9) . . . . ?
C7 C10 C15 C14 176.13(9) . . . . ?
C8 C7 C10 C11 98.71(11) . . . . ?
C8 C7 C10 C15 -78.55(11) . . . . ?
C8 C9 C29 C30 76.99(12) . . . . ?
C8 C9 C29 C34 -99.65(11) . . . . ?
C8 C16 C17 C18 -2.02(15) . . . . ?
C8 C16 C17 C21 178.35(9) . . . . ?
C9 O1 C6 C1 -17.81(15) . . . . ?
C9 O1 C6 C5 163.36(10) . . . . ?
C9 C8 C16 C17 -127.65(10) . . . . ?
C9 C8 C20 C19 129.05(10) . . . . ?
C9 C29 C30 C31 -174.36(9) . . . . ?
C9 C29 C34 C33 174.06(9) . . . . ?
C10 C7 C8 C9 178.89(8) . . . . ?
C10 C7 C8 C16 -65.44(11) . . . . ?
C10 C7 C8 C20 59.35(11) . . . . ?
C10 C11 C12 C13 -0.45(16) . . . . ?
C11 C10 C15 C14 -1.19(14) . . . . ?
C11 C12 C13 C14 -0.15(17) . . . . ?
C12 C13 C14 C15 0.07(16) . . . . ?
C13 C14 C15 C10 0.62(15) . . . . ?
C15 C10 C11 O2 -179.13(9) . . . . ?
C15 C10 C11 C12 1.10(15) . . . . ?
C16 C8 C9 O1 177.37(8) . . . . ?
C16 C8 C9 C29 54.96(11) . . . . ?
C16 C8 C20 C19 7.12(14) . . . . ?
C16 C17 C18 O3 -174.00(10) . . . . ?
C16 C17 C18 C19 6.43(14) . . . . ?
C16 C17 C21 C22 -1.97(16) . . . . ?
C16 C17 C21 C23 117.58(12) . . . . ?
C16 C17 C21 C24 -120.84(12) . . . . ?
C17 C18 C19 C20 -3.97(14) . . . . ?
C17 C18 C19 C25 177.20(9) . . . . ?
C18 C17 C21 C22 178.40(10) . . . . ?
C18 C17 C21 C23 -62.04(14) . . . . ?
C18 C17 C21 C24 59.53(13) . . . . ?
C18 C19 C20 C8 -3.08(15) . . . . ?
C18 C19 C25 C26 64.73(12) . . . . ?
C18 C19 C25 C27 -57.22(13) . . . . ?
C18 C19 C25 C28 -176.89(10) . . . . ?
C20 C8 C9 O1 52.76(10) . . . . ?
C20 C8 C9 C29 -69.65(10) . . . . ?
C20 C8 C16 C17 -4.39(14) . . . . ?
C20 C19 C25 C26 -114.04(11) . . . . ?
C20 C19 C25 C27 124.01(11) . . . . ?
C20 C19 C25 C28 4.34(15) . . . . ?
C21 C17 C18 O3 5.65(15) . . . . ?
C21 C17 C18 C19 -173.93(9) . . . . ?
C25 C19 C20 C8 175.70(9) . . . . ?
C29 C30 C31 C32 0.83(15) . . . . ?
C29 C30 C31 C35 179.04(10) . . . . ?
C30 C29 C34 C33 -2.71(16) . . . . ?
C30 C31 C32 O4 177.64(9) . . . . ?
C30 C31 C32 C33 -3.79(16) . . . . ?
C30 C31 C35 C36 8.55(15) . . . . ?
C30 C31 C35 C37 -110.70(11) . . . . ?
C30 C31 C35 C38 127.30(11) . . . . ?
C31 C32 C33 C34 3.43(16) . . . . ?
C31 C32 C33 C39 -176.73(10) . . . . ?
C32 C31 C35 C36 -173.34(11) . . . . ?
C32 C31 C35 C37 67.41(13) . . . . ?
C32 C31 C35 C38 -54.58(15) . . . . ?
C32 C33 C34 C29 -0.07(16) . . . . ?
C32 C33 C39 C40 -65.75(14) . . . . ?
C32 C33 C39 C41 57.11(15) . . . . ?
C32 C33 C39 C42 175.35(11) . . . . ?
C34 C29 C30 C31 2.29(15) . . . . ?
C34 C33 C39 C40 114.09(12) . . . . ?
C34 C33 C39 C41 -123.05(12) . . . . ?
C34 C33 C39 C42 -4.81(15) . . . . ?
C35 C31 C32 O4 -0.54(16) . . . . ?
C35 C31 C32 C33 178.02(10) . . . . ?
C39 C33 C34 C29 -179.92(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 1.817
_oxdiff_exptl_absorpt_empirical_full_min 0.567
