# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_190424LT
_database_code_depnum_ccdc_archive 'CCDC 1943157'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2021-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 O4'
_chemical_formula_weight         400.45

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.962(3)
_cell_length_b                   10.2398(15)
_cell_length_c                   11.0654(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.763(6)
_cell_angle_gamma                90
_cell_volume                     2030.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6958
_cell_measurement_theta_min      2.2726
_cell_measurement_theta_max      26.1119

_exptl_crystal_description       lump
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4629
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            28293
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.273
_diffrn_reflns_theta_max         26.665
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4214
_reflns_number_gt                3368
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.1235P)²+2.8622P] 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         4214
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.2262
_refine_ls_wR_factor_gt          0.2118
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.56708(11) 0.9836(2) 0.25810(19) 0.0304(5) Uani 1 1 d . . . . .
O2 O 0.55073(12) 0.8674(2) 0.05378(19) 0.0345(6) Uani 1 1 d . . . . .
O3 O 1.01743(10) 0.54586(17) 0.25487(15) 0.0179(4) Uani 1 1 d . . . . .
O4 O 0.92827(10) 0.70993(19) -0.06714(16) 0.0209(4) Uani 1 1 d . . . . .
C1 C 1.17766(15) 0.7194(3) 0.1570(2) 0.0209(6) Uani 1 1 d . . . . .
H1 H 1.2290 0.7270 0.1825 0.025 Uiso 1 1 calc R U . . .
C2 C 1.13159(15) 0.6392(2) 0.2198(2) 0.0183(5) Uani 1 1 d . . . . .
H10 H 1.1519 0.5907 0.2873 0.022 Uiso 1 1 calc R U . . .
C3 C 1.05599(14) 0.6288(2) 0.1851(2) 0.0158(5) Uani 1 1 d . . . . .
C4 C 1.02608(14) 0.6997(2) 0.0848(2) 0.0142(5) Uani 1 1 d . . . . .
C5 C 0.94522(14) 0.7052(2) 0.0404(2) 0.0150(5) Uani 1 1 d . . . . .
C6 C 0.88891(14) 0.7130(2) 0.1351(2) 0.0146(5) Uani 1 1 d . . . . .
H22 H 0.8957 0.7918 0.1881 0.018 Uiso 1 1 calc R U . . .
C7 C 0.80751(14) 0.6946(2) 0.0842(2) 0.0153(5) Uani 1 1 d . . . . .
H8 H 0.8040 0.6990 -0.0063 0.018 Uiso 1 1 calc R U . . .
C8 C 0.74765(14) 0.7760(2) 0.1357(2) 0.0156(5) Uani 1 1 d . . . . .
C9 C 0.67780(15) 0.7801(3) 0.0715(2) 0.0212(6) Uani 1 1 d . . . . .
H7 H 0.6705 0.7331 -0.0024 0.025 Uiso 1 1 calc R U . . .
C10 C 0.61899(15) 0.8515(3) 0.1134(2) 0.0237(6) Uani 1 1 d . . . . .
C11 C 0.62895(15) 0.9190(3) 0.2236(2) 0.0210(6) Uani 1 1 d . . . . .
C12 C 0.57398(19) 1.0508(3) 0.3701(3) 0.0327(7) Uani 1 1 d . . . . .
H2 H 0.5890 0.9893 0.4350 0.049 Uiso 1 1 calc R U . . .
H25 H 0.5259 1.0901 0.3864 0.049 Uiso 1 1 calc R U . . .
H3 H 0.6118 1.1195 0.3664 0.049 Uiso 1 1 calc R U . . .
C13 C 0.53867(16) 0.8106(3) -0.0628(3) 0.0298(7) Uani 1 1 d . . . . .
H6 H 0.5812 0.8301 -0.1110 0.045 Uiso 1 1 calc R U . . .
H5 H 0.4930 0.8466 -0.1032 0.045 Uiso 1 1 calc R U . . .
H4 H 0.5335 0.7157 -0.0547 0.045 Uiso 1 1 calc R U . . .
C14 C 0.88427(14) 0.5836(2) 0.2085(2) 0.0150(5) Uani 1 1 d . . . . .
H15 H 0.8728 0.6006 0.2943 0.018 Uiso 1 1 calc R U . . .
C15 C 0.94894(14) 0.4914(2) 0.2012(2) 0.0171(5) Uani 1 1 d . . . . .
H14 H 0.9378 0.4090 0.2433 0.021 Uiso 1 1 calc R U . . .
H13 H 0.9554 0.4703 0.1152 0.021 Uiso 1 1 calc R U . . .
C16 C 1.07446(15) 0.7777(3) 0.0206(2) 0.0195(6) Uani 1 1 d . . . . .
H12 H 1.0553 0.8235 -0.0494 0.023 Uiso 1 1 calc R U . . .
C17 C 1.14870(15) 0.7891(3) 0.0567(2) 0.0211(6) Uani 1 1 d . . . . .
H11 H 1.1802 0.8442 0.0134 0.025 Uiso 1 1 calc R U . . .
C18 C 0.81331(14) 0.5474(2) 0.1292(2) 0.0167(5) Uani 1 1 d . . . . .
H16 H 0.8283 0.4920 0.0605 0.020 Uiso 1 1 calc R U . . .
C19 C 0.74781(15) 0.4846(3) 0.1827(3) 0.0224(6) Uani 1 1 d . . . . .
C20 C 0.70644(17) 0.3924(3) 0.1131(3) 0.0319(7) Uani 1 1 d . . . . .
H21 H 0.7221 0.3681 0.0359 0.038 Uiso 1 1 calc R U . . .
C21 C 0.64319(19) 0.3364(4) 0.1552(4) 0.0446(9) Uani 1 1 d . . . . .
H17 H 0.6152 0.2753 0.1061 0.053 Uiso 1 1 calc R U . . .
C22 C 0.62062(18) 0.3682(3) 0.2671(4) 0.0488(11) Uani 1 1 d . . . . .
H18 H 0.5763 0.3311 0.2947 0.059 Uiso 1 1 calc R U . . .
C23 C 0.6625(2) 0.4550(3) 0.3405(4) 0.0429(9) Uani 1 1 d . . . . .
H19 H 0.6483 0.4745 0.4196 0.052 Uiso 1 1 calc R U . . .
C24 C 0.72558(18) 0.5132(3) 0.2968(3) 0.0311(7) Uani 1 1 d . . . . .
H20 H 0.7537 0.5736 0.3464 0.037 Uiso 1 1 calc R U . . .
C25 C 0.75687(14) 0.8454(2) 0.2432(2) 0.0161(5) Uani 1 1 d . . . . .
H23 H 0.8038 0.8447 0.2881 0.019 Uiso 1 1 calc R U . . .
C26 C 0.69754(15) 0.9165(3) 0.2862(2) 0.0199(6) Uani 1 1 d . . . . .
H24 H 0.7048 0.9638 0.3599 0.024 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 C11 1.369(3) . ?
O1 C12 1.415(4) . ?
O2 C10 1.363(3) . ?
O2 C13 1.419(4) . ?
O3 C3 1.366(3) . ?
O3 C15 1.443(3) . ?
O4 C5 1.210(3) . ?
C1 C2 1.385(4) . ?
C1 C17 1.391(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(4) . ?
C2 H10 0.9500 . ?
C3 C4 1.404(3) . ?
C4 C16 1.407(4) . ?
C4 C5 1.503(3) . ?
C5 C6 1.505(3) . ?
C6 C7 1.543(3) . ?
C6 C14 1.559(3) . ?
C6 H22 1.0000 . ?
C7 C8 1.502(3) . ?
C7 C18 1.589(3) . ?
C7 H8 1.0000 . ?
C8 C25 1.387(3) . ?
C8 C9 1.401(4) . ?
C9 C10 1.389(4) . ?
C9 H7 0.9500 . ?
C10 C11 1.403(4) . ?
C11 C26 1.373(4) . ?
C12 H2 0.9800 . ?
C12 H25 0.9800 . ?
C12 H3 0.9800 . ?
C13 H6 0.9800 . ?
C13 H5 0.9800 . ?
C13 H4 0.9800 . ?
C14 C15 1.503(3) . ?
C14 C18 1.544(3) . ?
C14 H15 1.0000 . ?
C15 H14 0.9900 . ?
C15 H13 0.9900 . ?
C16 C17 1.372(4) . ?
C16 H12 0.9500 . ?
C17 H11 0.9500 . ?
C18 C19 1.497(4) . ?
C18 H16 1.0000 . ?
C19 C24 1.380(4) . ?
C19 C20 1.400(4) . ?
C20 C21 1.381(4) . ?
C20 H21 0.9500 . ?
C21 C22 1.368(6) . ?
C21 H17 0.9500 . ?
C22 C23 1.391(6) . ?
C22 H18 0.9500 . ?
C23 C24 1.394(4) . ?
C23 H19 0.9500 . ?
C24 H20 0.9500 . ?
C25 C26 1.400(4) . ?
C25 H23 0.9500 . ?
C26 H24 0.9500 . ?

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
C11 O1 C12 116.9(2) . . ?
C10 O2 C13 118.0(2) . . ?
C3 O3 C15 117.24(18) . . ?
C2 C1 C17 120.0(2) . . ?
C2 C1 H1 120.0 . . ?
C17 C1 H1 120.0 . . ?
C1 C2 C3 120.8(2) . . ?
C1 C2 H10 119.6 . . ?
C3 C2 H10 119.6 . . ?
O3 C3 C2 114.5(2) . . ?
O3 C3 C4 125.9(2) . . ?
C2 C3 C4 119.6(2) . . ?
C3 C4 C16 118.4(2) . . ?
C3 C4 C5 126.1(2) . . ?
C16 C4 C5 115.4(2) . . ?
O4 C5 C4 119.9(2) . . ?
O4 C5 C6 123.0(2) . . ?
C4 C5 C6 116.9(2) . . ?
C5 C6 C7 113.8(2) . . ?
C5 C6 C14 112.3(2) . . ?
C7 C6 C14 90.27(18) . . ?
C5 C6 H22 112.9 . . ?
C7 C6 H22 112.9 . . ?
C14 C6 H22 112.9 . . ?
C8 C7 C6 118.6(2) . . ?
C8 C7 C18 116.2(2) . . ?
C6 C7 C18 87.73(18) . . ?
C8 C7 H8 110.8 . . ?
C6 C7 H8 110.8 . . ?
C18 C7 H8 110.8 . . ?
C25 C8 C9 118.2(2) . . ?
C25 C8 C7 124.2(2) . . ?
C9 C8 C7 117.6(2) . . ?
C10 C9 C8 121.5(2) . . ?
C10 C9 H7 119.3 . . ?
C8 C9 H7 119.3 . . ?
O2 C10 C9 125.5(3) . . ?
O2 C10 C11 114.9(2) . . ?
C9 C10 C11 119.5(2) . . ?
O1 C11 C26 125.9(2) . . ?
O1 C11 C10 114.9(2) . . ?
C26 C11 C10 119.2(2) . . ?
O1 C12 H2 109.5 . . ?
O1 C12 H25 109.5 . . ?
H2 C12 H25 109.5 . . ?
O1 C12 H3 109.5 . . ?
H2 C12 H3 109.5 . . ?
H25 C12 H3 109.5 . . ?
O2 C13 H6 109.5 . . ?
O2 C13 H5 109.5 . . ?
H6 C13 H5 109.5 . . ?
O2 C13 H4 109.5 . . ?
H6 C13 H4 109.5 . . ?
H5 C13 H4 109.5 . . ?
C15 C14 C18 115.5(2) . . ?
C15 C14 C6 116.0(2) . . ?
C18 C14 C6 88.76(18) . . ?
C15 C14 H15 111.6 . . ?
C18 C14 H15 111.6 . . ?
C6 C14 H15 111.6 . . ?
O3 C15 C14 112.1(2) . . ?
O3 C15 H14 109.2 . . ?
C14 C15 H14 109.2 . . ?
O3 C15 H13 109.2 . . ?
C14 C15 H13 109.2 . . ?
H14 C15 H13 107.9 . . ?
C17 C16 C4 121.5(2) . . ?
C17 C16 H12 119.3 . . ?
C4 C16 H12 119.3 . . ?
C16 C17 C1 119.6(3) . . ?
C16 C17 H11 120.2 . . ?
C1 C17 H11 120.2 . . ?
C19 C18 C14 121.3(2) . . ?
C19 C18 C7 119.6(2) . . ?
C14 C18 C7 89.13(18) . . ?
C19 C18 H16 108.4 . . ?
C14 C18 H16 108.4 . . ?
C7 C18 H16 108.4 . . ?
C24 C19 C20 118.1(3) . . ?
C24 C19 C18 123.5(3) . . ?
C20 C19 C18 118.3(3) . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H21 119.6 . . ?
C19 C20 H21 119.6 . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H17 119.8 . . ?
C20 C21 H17 119.8 . . ?
C21 C22 C23 120.0(3) . . ?
C21 C22 H18 120.0 . . ?
C23 C22 H18 120.0 . . ?
C22 C23 C24 119.5(3) . . ?
C22 C23 H19 120.3 . . ?
C24 C23 H19 120.3 . . ?
C19 C24 C23 121.1(3) . . ?
C19 C24 H20 119.5 . . ?
C23 C24 H20 119.5 . . ?
C8 C25 C26 120.5(2) . . ?
C8 C25 H23 119.7 . . ?
C26 C25 H23 119.7 . . ?
C11 C26 C25 121.1(2) . . ?
C11 C26 H24 119.5 . . ?
C25 C26 H24 119.5 . . ?

_refine_diff_density_max         0.694
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.094

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_mo_190608LT_0m
_database_code_depnum_ccdc_archive 'CCDC 1943160'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2021-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 O4'
_chemical_formula_weight         400.45

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                   9.4174(5)
_cell_length_b                   10.5047(5)
_cell_length_c                   11.7070(6)
_cell_angle_alpha                92.823(2)
_cell_angle_beta                 108.693(2)
_cell_angle_gamma                109.839(2)
_cell_volume                     1015.58(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8284
_cell_measurement_theta_min      2.4633
_cell_measurement_theta_max      26.3517

_exptl_crystal_description       lump
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7241
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            23935
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.866
_diffrn_reflns_theta_max         26.432
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4180
_reflns_number_gt                3553
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.0409P)²+0.4300P] 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         4180
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0909
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 -0.16568(12) -0.06699(10) 0.24219(10) 0.0284(2) Uani 1 1 d . . . . .
O2 O 0.27615(11) 0.14713(9) 0.11257(8) 0.0199(2) Uani 1 1 d . . . . .
O3 O 0.36246(11) 0.68541(9) -0.09233(8) 0.0196(2) Uani 1 1 d . . . . .
O4 O 0.02804(10) 0.30710(9) -0.08098(8) 0.0194(2) Uani 1 1 d . . . . .
C1 C -0.2730(2) -0.05415(16) 0.30007(17) 0.0390(4) Uani 1 1 d . . . . .
H24 H -0.2105 0.0049 0.3807 0.059 Uiso 1 1 calc R U . . .
H3 H -0.3376 -0.1453 0.3100 0.059 Uiso 1 1 calc R U . . .
H1 H -0.3449 -0.0132 0.2495 0.059 Uiso 1 1 calc R U . . .
C2 C -0.06198(15) 0.05254(13) 0.22551(12) 0.0190(3) Uani 1 1 d . . . . .
C3 C -0.06525(15) 0.18111(13) 0.25153(12) 0.0182(3) Uani 1 1 d . . . . .
H4 H -0.1415 0.1921 0.2841 0.022 Uiso 1 1 calc R U . . .
C4 C 0.04620(15) 0.29465(12) 0.22884(11) 0.0154(3) Uani 1 1 d . . . . .
H5 H 0.0444 0.3832 0.2466 0.018 Uiso 1 1 calc R U . . .
C5 C 0.15875(14) 0.28268(12) 0.18151(11) 0.0140(2) Uani 1 1 d . . . . .
C6 C 0.28781(14) 0.40487(12) 0.16657(11) 0.0135(2) Uani 1 1 d . . . . .
H10 H 0.3943 0.4073 0.2231 0.016 Uiso 1 1 calc R U . . .
C7 C 0.30665(14) 0.43374(12) 0.04166(11) 0.0137(2) Uani 1 1 d . . . . .
H23 H 0.3948 0.4084 0.0298 0.016 Uiso 1 1 calc R U . . .
C8 C 0.15938(14) 0.38924(12) -0.07349(11) 0.0145(2) Uani 1 1 d . . . . .
C9 C 0.18253(15) 0.44433(13) -0.18567(11) 0.0159(3) Uani 1 1 d . . . . .
C10 C 0.27827(15) 0.57832(13) -0.18933(12) 0.0167(3) Uani 1 1 d . . . . .
C11 C 0.29100(16) 0.61365(14) -0.30034(12) 0.0204(3) Uani 1 1 d . . . . .
H18 H 0.3566 0.7045 -0.3020 0.025 Uiso 1 1 calc R U . . .
C12 C 0.20951(16) 0.51813(15) -0.40754(12) 0.0225(3) Uani 1 1 d . . . . .
H2 H 0.2191 0.5434 -0.4823 0.027 Uiso 1 1 calc R U . . .
C13 C 0.15931(15) 0.15017(12) 0.15691(11) 0.0155(3) Uani 1 1 d . . . . .
C14 C 0.29193(17) 0.01833(13) 0.09298(13) 0.0220(3) Uani 1 1 d . . . . .
H6 H 0.3164 -0.0159 0.1705 0.033 Uiso 1 1 calc R U . . .
H8 H 0.3798 0.0303 0.0619 0.033 Uiso 1 1 calc R U . . .
H7 H 0.1905 -0.0480 0.0331 0.033 Uiso 1 1 calc R U . . .
C15 C 0.05056(16) 0.03588(13) 0.17793(12) 0.0188(3) Uani 1 1 d . . . . .
H9 H 0.0521 -0.0528 0.1603 0.023 Uiso 1 1 calc R U . . .
C16 C 0.36705(15) 0.59017(12) 0.09381(11) 0.0146(2) Uani 1 1 d . . . . .
H17 H 0.4875 0.6310 0.1339 0.018 Uiso 1 1 calc R U . . .
C17 C 0.28509(14) 0.54997(12) 0.18985(11) 0.0135(2) Uani 1 1 d . . . . .
H16 H 0.1709 0.5443 0.1549 0.016 Uiso 1 1 calc R U . . .
C18 C 0.36543(14) 0.63789(12) 0.31526(11) 0.0141(2) Uani 1 1 d . . . . .
C19 C 0.50036(16) 0.62795(13) 0.40232(12) 0.0189(3) Uani 1 1 d . . . . .
H15 H 0.5392 0.5596 0.3847 0.023 Uiso 1 1 calc R U . . .
C20 C 0.57926(17) 0.71658(14) 0.51475(12) 0.0225(3) Uani 1 1 d . . . . .
H14 H 0.6720 0.7093 0.5730 0.027 Uiso 1 1 calc R U . . .
C21 C 0.52242(17) 0.81531(13) 0.54165(12) 0.0232(3) Uani 1 1 d . . . . .
H13 H 0.5760 0.8760 0.6184 0.028 Uiso 1 1 calc R U . . .
C22 C 0.38689(17) 0.82535(13) 0.45618(13) 0.0230(3) Uani 1 1 d . . . . .
H12 H 0.3469 0.8923 0.4748 0.028 Uiso 1 1 calc R U . . .
C23 C 0.30961(15) 0.73783(13) 0.34356(12) 0.0181(3) Uani 1 1 d . . . . .
H11 H 0.2177 0.7461 0.2851 0.022 Uiso 1 1 calc R U . . .
C24 C 0.30670(16) 0.67860(13) 0.00878(11) 0.0178(3) Uani 1 1 d . . . . .
H22 H 0.1870 0.6408 -0.0230 0.021 Uiso 1 1 calc R U . . .
H21 H 0.3444 0.7726 0.0550 0.021 Uiso 1 1 calc R U . . .
C25 C 0.10072(15) 0.34971(14) -0.29663(12) 0.0195(3) Uani 1 1 d . . . . .
H20 H 0.0345 0.2585 -0.2964 0.023 Uiso 1 1 calc R U . . .
C26 C 0.11369(16) 0.38520(15) -0.40582(12) 0.0224(3) Uani 1 1 d . . . . .
H19 H 0.0574 0.3191 -0.4793 0.027 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 1.3720(15) . ?
O1 C1 1.4217(18) . ?
O2 C13 1.3673(15) . ?
O2 C14 1.4259(14) . ?
O3 C10 1.3694(15) . ?
O3 C24 1.4364(15) . ?
O4 C8 1.2168(15) . ?
C1 H24 0.9800 . ?
C1 H3 0.9800 . ?
C1 H1 0.9800 . ?
C2 C3 1.3826(18) . ?
C2 C15 1.3996(18) . ?
C3 C4 1.3983(17) . ?
C3 H4 0.9500 . ?
C4 C5 1.3807(17) . ?
C4 H5 0.9500 . ?
C5 C13 1.4096(16) . ?
C5 C6 1.5016(16) . ?
C6 C17 1.5453(16) . ?
C6 C7 1.5606(16) . ?
C6 H10 1.0000 . ?
C7 C8 1.5029(17) . ?
C7 C16 1.5623(16) . ?
C7 H23 1.0000 . ?
C8 C9 1.5100(17) . ?
C9 C10 1.4019(18) . ?
C9 C25 1.4073(18) . ?
C10 C11 1.3993(18) . ?
C11 C12 1.381(2) . ?
C11 H18 0.9500 . ?
C12 C26 1.387(2) . ?
C12 H2 0.9500 . ?
C13 C15 1.3808(18) . ?
C14 H6 0.9800 . ?
C14 H8 0.9800 . ?
C14 H7 0.9800 . ?
C15 H9 0.9500 . ?
C16 C24 1.5045(17) . ?
C16 C17 1.5557(16) . ?
C16 H17 1.0000 . ?
C17 C18 1.5036(17) . ?
C17 H16 1.0000 . ?
C18 C19 1.3909(18) . ?
C18 C23 1.3930(17) . ?
C19 C20 1.3907(19) . ?
C19 H15 0.9500 . ?
C20 C21 1.3834(19) . ?
C20 H14 0.9500 . ?
C21 C22 1.387(2) . ?
C21 H13 0.9500 . ?
C22 C23 1.3873(18) . ?
C22 H12 0.9500 . ?
C23 H11 0.9500 . ?
C24 H22 0.9900 . ?
C24 H21 0.9900 . ?
C25 C26 1.3799(19) . ?
C25 H20 0.9500 . ?
C26 H19 0.9500 . ?

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 C1 116.82(11) . . ?
C13 O2 C14 117.60(10) . . ?
C10 O3 C24 117.10(10) . . ?
O1 C1 H24 109.5 . . ?
O1 C1 H3 109.5 . . ?
H24 C1 H3 109.5 . . ?
O1 C1 H1 109.5 . . ?
H24 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
O1 C2 C3 124.28(12) . . ?
O1 C2 C15 114.75(11) . . ?
C3 C2 C15 120.96(11) . . ?
C2 C3 C4 118.54(11) . . ?
C2 C3 H4 120.7 . . ?
C4 C3 H4 120.7 . . ?
C5 C4 C3 122.35(11) . . ?
C5 C4 H5 118.8 . . ?
C3 C4 H5 118.8 . . ?
C4 C5 C13 117.54(11) . . ?
C4 C5 C6 122.79(11) . . ?
C13 C5 C6 119.42(11) . . ?
C5 C6 C17 119.66(10) . . ?
C5 C6 C7 124.66(10) . . ?
C17 C6 C7 88.86(9) . . ?
C5 C6 H10 107.2 . . ?
C17 C6 H10 107.2 . . ?
C7 C6 H10 107.2 . . ?
C8 C7 C6 119.85(10) . . ?
C8 C7 C16 111.91(10) . . ?
C6 C7 C16 87.41(9) . . ?
C8 C7 H23 111.8 . . ?
C6 C7 H23 111.8 . . ?
C16 C7 H23 111.8 . . ?
O4 C8 C7 123.22(11) . . ?
O4 C8 C9 119.86(11) . . ?
C7 C8 C9 116.80(10) . . ?
C10 C9 C25 117.57(11) . . ?
C10 C9 C8 126.56(11) . . ?
C25 C9 C8 115.86(11) . . ?
O3 C10 C11 113.73(11) . . ?
O3 C10 C9 126.17(11) . . ?
C11 C10 C9 120.08(12) . . ?
C12 C11 C10 120.87(12) . . ?
C12 C11 H18 119.6 . . ?
C10 C11 H18 119.6 . . ?
C11 C12 C26 119.88(12) . . ?
C11 C12 H2 120.1 . . ?
C26 C12 H2 120.1 . . ?
O2 C13 C15 124.39(11) . . ?
O2 C13 C5 114.06(10) . . ?
C15 C13 C5 121.54(11) . . ?
O2 C14 H6 109.5 . . ?
O2 C14 H8 109.5 . . ?
H6 C14 H8 109.5 . . ?
O2 C14 H7 109.5 . . ?
H6 C14 H7 109.5 . . ?
H8 C14 H7 109.5 . . ?
C13 C15 C2 119.06(11) . . ?
C13 C15 H9 120.5 . . ?
C2 C15 H9 120.5 . . ?
C24 C16 C17 115.96(10) . . ?
C24 C16 C7 117.31(10) . . ?
C17 C16 C7 88.42(9) . . ?
C24 C16 H17 111.1 . . ?
C17 C16 H17 111.1 . . ?
C7 C16 H17 111.1 . . ?
C18 C17 C6 121.92(10) . . ?
C18 C17 C16 117.97(10) . . ?
C6 C17 C16 88.19(8) . . ?
C18 C17 H16 109.0 . . ?
C6 C17 H16 109.0 . . ?
C16 C17 H16 109.0 . . ?
C19 C18 C23 118.53(11) . . ?
C19 C18 C17 121.93(11) . . ?
C23 C18 C17 119.44(11) . . ?
C20 C19 C18 120.94(12) . . ?
C20 C19 H15 119.5 . . ?
C18 C19 H15 119.5 . . ?
C21 C20 C19 119.90(12) . . ?
C21 C20 H14 120.1 . . ?
C19 C20 H14 120.1 . . ?
C20 C21 C22 119.76(12) . . ?
C20 C21 H13 120.1 . . ?
C22 C21 H13 120.1 . . ?
C21 C22 C23 120.19(12) . . ?
C21 C22 H12 119.9 . . ?
C23 C22 H12 119.9 . . ?
C22 C23 C18 120.67(12) . . ?
C22 C23 H11 119.7 . . ?
C18 C23 H11 119.7 . . ?
O3 C24 C16 111.84(10) . . ?
O3 C24 H22 109.2 . . ?
C16 C24 H22 109.2 . . ?
O3 C24 H21 109.2 . . ?
C16 C24 H21 109.2 . . ?
H22 C24 H21 107.9 . . ?
C26 C25 C9 122.07(12) . . ?
C26 C25 H20 119.0 . . ?
C9 C25 H20 119.0 . . ?
C25 C26 C12 119.53(12) . . ?
C25 C26 H19 120.2 . . ?
C12 C26 H19 120.2 . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.041

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_190443LT_a
_database_code_depnum_ccdc_archive 'CCDC 1943159'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2021-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 O4'
_chemical_formula_weight         400.45

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.8730(7)
_cell_length_b                   22.7202(12)
_cell_length_c                   6.3384(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.843(2)
_cell_angle_gamma                90
_cell_volume                     1974.10(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5503
_cell_measurement_theta_min      2.9720
_cell_measurement_theta_max      26.2713

_exptl_crystal_description       tabullar
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6781
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            14699
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.485
_diffrn_reflns_theta_max         26.410
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4040
_reflns_number_gt                3358
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.0558P)²+4.0705P] 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         4040
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0716
_refine_ls_wR_factor_ref         0.1787
_refine_ls_wR_factor_gt          0.1719
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.001
_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 0.18759(15) 0.31702(9) 1.2573(3) 0.0268(5) Uani 1 1 d . . . . .
O2 O 0.28397(15) 0.31790(8) 0.9469(3) 0.0227(5) Uani 1 1 d . . . . .
O3 O 0.11833(17) 0.52213(10) 0.7677(4) 0.0383(6) Uani 1 1 d . . . . .
O4 O 0.19947(15) 0.69222(9) 0.6180(3) 0.0217(5) Uani 1 1 d . . . . .
C1 C 0.1259(2) 0.31417(15) 1.4176(5) 0.0318(7) Uani 1 1 d . . . . .
H24 H 0.1584 0.3331 1.5484 0.048 Uiso 1 1 calc R U . . .
H3 H 0.1125 0.2729 1.4475 0.048 Uiso 1 1 calc R U . . .
H1 H 0.0644 0.3345 1.3671 0.048 Uiso 1 1 calc R U . . .
C2 C 0.2155(2) 0.37206(12) 1.2040(4) 0.0190(6) Uani 1 1 d . . . . .
C3 C 0.27023(19) 0.37247(12) 1.0274(4) 0.0193(6) Uani 1 1 d . . . . .
C4 C 0.3033(2) 0.42557(13) 0.9597(4) 0.0218(6) Uani 1 1 d . . . . .
H7 H 0.3401 0.4262 0.8451 0.026 Uiso 1 1 calc R U . . .
C5 C 0.28324(19) 0.47876(12) 1.0586(4) 0.0194(6) Uani 1 1 d . . . . .
C6 C 0.3212(2) 0.53632(13) 0.9778(4) 0.0205(6) Uani 1 1 d . . . . .
H8 H 0.3923 0.5313 0.9713 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2729(2) 0.56707(13) 0.7655(4) 0.0196(6) Uani 1 1 d . . . . .
H9 H 0.3110 0.5604 0.6459 0.024 Uiso 1 1 calc R U . . .
C8 C 0.1650(2) 0.55959(12) 0.6951(4) 0.0193(6) Uani 1 1 d . . . . .
C9 C 0.11691(19) 0.59842(12) 0.5149(4) 0.0171(6) Uani 1 1 d . . . . .
C10 C 0.13517(19) 0.65795(12) 0.4847(4) 0.0171(6) Uani 1 1 d . . . . .
C11 C 0.0839(2) 0.68789(13) 0.3098(4) 0.0213(6) Uani 1 1 d . . . . .
H12 H 0.0958 0.7286 0.2913 0.026 Uiso 1 1 calc R U . . .
C12 C 0.0162(2) 0.65895(14) 0.1638(4) 0.0235(6) Uani 1 1 d . . . . .
H2 H -0.0177 0.6797 0.0450 0.028 Uiso 1 1 calc R U . . .
C13 C 0.3449(2) 0.31585(14) 0.7833(5) 0.0291(7) Uani 1 1 d . . . . .
H4 H 0.3186 0.3423 0.6664 0.044 Uiso 1 1 calc R U . . .
H6 H 0.3466 0.2755 0.7288 0.044 Uiso 1 1 calc R U . . .
H5 H 0.4112 0.3283 0.8429 0.044 Uiso 1 1 calc R U . . .
C14 C 0.30782(19) 0.59524(11) 1.0937(4) 0.0160(5) Uani 1 1 d . . . . .
H16 H 0.2429 0.5947 1.1436 0.019 Uiso 1 1 calc R U . . .
C15 C 0.2971(2) 0.62781(12) 0.8771(4) 0.0197(6) Uani 1 1 d . . . . .
H15 H 0.3614 0.6431 0.8485 0.024 Uiso 1 1 calc R U . . .
C16 C 0.0470(2) 0.57030(13) 0.3652(5) 0.0223(6) Uani 1 1 d . . . . .
H14 H 0.0332 0.5299 0.3851 0.027 Uiso 1 1 calc R U . . .
C17 C -0.0025(2) 0.59932(14) 0.1901(5) 0.0248(7) Uani 1 1 d . . . . .
H13 H -0.0485 0.5790 0.0893 0.030 Uiso 1 1 calc R U . . .
C18 C 0.2198(2) 0.67432(12) 0.8386(4) 0.0218(6) Uani 1 1 d . . . . .
H10 H 0.1592 0.6592 0.8832 0.026 Uiso 1 1 calc R U . . .
H11 H 0.2411 0.7091 0.9279 0.026 Uiso 1 1 calc R U . . .
C19 C 0.38315(19) 0.61663(12) 1.2739(4) 0.0165(5) Uani 1 1 d . . . . .
C20 C 0.4542(2) 0.57946(13) 1.3804(5) 0.0229(6) Uani 1 1 d . . . . .
H21 H 0.4561 0.5394 1.3389 0.027 Uiso 1 1 calc R U . . .
C21 C 0.5224(2) 0.60054(13) 1.5471(5) 0.0254(7) Uani 1 1 d . . . . .
H20 H 0.5701 0.5746 1.6198 0.031 Uiso 1 1 calc R U . . .
C22 C 0.5212(2) 0.65932(13) 1.6080(4) 0.0215(6) Uani 1 1 d . . . . .
H19 H 0.5678 0.6737 1.7221 0.026 Uiso 1 1 calc R U . . .
C23 C 0.4516(2) 0.69670(13) 1.5009(4) 0.0205(6) Uani 1 1 d . . . . .
H18 H 0.4510 0.7371 1.5393 0.025 Uiso 1 1 calc R U . . .
C24 C 0.3825(2) 0.67516(12) 1.3371(4) 0.0187(6) Uani 1 1 d . . . . .
H17 H 0.3339 0.7009 1.2671 0.022 Uiso 1 1 calc R U . . .
C25 C 0.2329(2) 0.47678(13) 1.2278(5) 0.0227(6) Uani 1 1 d . . . . .
H22 H 0.2209 0.5124 1.2978 0.027 Uiso 1 1 calc R U . . .
C26 C 0.1986(2) 0.42369(13) 1.3008(5) 0.0242(6) Uani 1 1 d . . . . .
H23 H 0.1634 0.4237 1.4182 0.029 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 1.367(3) . ?
O1 C1 1.428(4) . ?
O2 C3 1.365(3) . ?
O2 C13 1.436(4) . ?
O3 C8 1.203(4) . ?
O4 C10 1.373(3) . ?
O4 C18 1.442(3) . ?
C1 H24 0.9800 . ?
C1 H3 0.9800 . ?
C1 H1 0.9800 . ?
C2 C26 1.361(4) . ?
C2 C3 1.446(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.409(4) . ?
C4 H7 0.9500 . ?
C5 C25 1.367(4) . ?
C5 C6 1.527(4) . ?
C6 C14 1.552(4) . ?
C6 C7 1.572(4) . ?
C6 H8 1.0000 . ?
C7 C8 1.505(4) . ?
C7 C15 1.564(4) . ?
C7 H9 1.0000 . ?
C8 C9 1.515(4) . ?
C9 C10 1.395(4) . ?
C9 C16 1.402(4) . ?
C10 C11 1.398(4) . ?
C11 C12 1.379(4) . ?
C11 H12 0.9500 . ?
C12 C17 1.394(4) . ?
C12 H2 0.9500 . ?
C13 H4 0.9800 . ?
C13 H6 0.9800 . ?
C13 H5 0.9800 . ?
C14 C19 1.505(4) . ?
C14 C15 1.547(4) . ?
C14 H16 1.0000 . ?
C15 C18 1.498(4) . ?
C15 H15 1.0000 . ?
C16 C17 1.380(4) . ?
C16 H14 0.9500 . ?
C17 H13 0.9500 . ?
C18 H10 0.9900 . ?
C18 H11 0.9900 . ?
C19 C24 1.390(4) . ?
C19 C20 1.391(4) . ?
C20 C21 1.391(4) . ?
C20 H21 0.9500 . ?
C21 C22 1.391(4) . ?
C21 H20 0.9500 . ?
C22 C23 1.383(4) . ?
C22 H19 0.9500 . ?
C23 C24 1.389(4) . ?
C23 H18 0.9500 . ?
C24 H17 0.9500 . ?
C25 C26 1.402(4) . ?
C25 H22 0.9500 . ?
C26 H23 0.9500 . ?

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 C1 116.2(2) . . ?
C3 O2 C13 115.5(2) . . ?
C10 O4 C18 116.7(2) . . ?
O1 C1 H24 109.5 . . ?
O1 C1 H3 109.5 . . ?
H24 C1 H3 109.5 . . ?
O1 C1 H1 109.5 . . ?
H24 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
C26 C2 O1 127.0(3) . . ?
C26 C2 C3 119.4(3) . . ?
O1 C2 C3 113.5(2) . . ?
O2 C3 C4 127.2(3) . . ?
O2 C3 C2 113.8(2) . . ?
C4 C3 C2 119.0(3) . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H7 119.6 . . ?
C5 C4 H7 119.6 . . ?
C25 C5 C4 118.7(3) . . ?
C25 C5 C6 122.3(3) . . ?
C4 C5 C6 118.9(3) . . ?
C5 C6 C14 120.5(2) . . ?
C5 C6 C7 123.0(2) . . ?
C14 C6 C7 87.5(2) . . ?
C5 C6 H8 108.0 . . ?
C14 C6 H8 108.0 . . ?
C7 C6 H8 108.0 . . ?
C8 C7 C15 111.6(2) . . ?
C8 C7 C6 118.5(2) . . ?
C15 C7 C6 88.37(19) . . ?
C8 C7 H9 112.1 . . ?
C15 C7 H9 112.1 . . ?
C6 C7 H9 112.1 . . ?
O3 C8 C7 122.4(3) . . ?
O3 C8 C9 120.0(2) . . ?
C7 C8 C9 117.4(2) . . ?
C10 C9 C16 118.1(2) . . ?
C10 C9 C8 126.9(2) . . ?
C16 C9 C8 115.1(2) . . ?
O4 C10 C9 125.5(2) . . ?
O4 C10 C11 114.5(2) . . ?
C9 C10 C11 120.0(2) . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H12 119.6 . . ?
C10 C11 H12 119.6 . . ?
C11 C12 C17 120.2(3) . . ?
C11 C12 H2 119.9 . . ?
C17 C12 H2 119.9 . . ?
O2 C13 H4 109.5 . . ?
O2 C13 H6 109.5 . . ?
H4 C13 H6 109.5 . . ?
O2 C13 H5 109.5 . . ?
H4 C13 H5 109.5 . . ?
H6 C13 H5 109.5 . . ?
C19 C14 C15 118.7(2) . . ?
C19 C14 C6 121.2(2) . . ?
C15 C14 C6 89.7(2) . . ?
C19 C14 H16 108.6 . . ?
C15 C14 H16 108.6 . . ?
C6 C14 H16 108.6 . . ?
C18 C15 C14 116.8(2) . . ?
C18 C15 C7 116.8(2) . . ?
C14 C15 C7 87.9(2) . . ?
C18 C15 H15 111.1 . . ?
C14 C15 H15 111.1 . . ?
C7 C15 H15 111.1 . . ?
C17 C16 C9 122.2(3) . . ?
C17 C16 H14 118.9 . . ?
C9 C16 H14 118.9 . . ?
C16 C17 C12 118.8(3) . . ?
C16 C17 H13 120.6 . . ?
C12 C17 H13 120.6 . . ?
O4 C18 C15 112.7(2) . . ?
O4 C18 H10 109.1 . . ?
C15 C18 H10 109.1 . . ?
O4 C18 H11 109.1 . . ?
C15 C18 H11 109.1 . . ?
H10 C18 H11 107.8 . . ?
C24 C19 C20 118.5(2) . . ?
C24 C19 C14 119.5(2) . . ?
C20 C19 C14 122.0(2) . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H21 119.7 . . ?
C19 C20 H21 119.7 . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H20 119.8 . . ?
C22 C21 H20 119.8 . . ?
C23 C22 C21 119.4(3) . . ?
C23 C22 H19 120.3 . . ?
C21 C22 H19 120.3 . . ?
C22 C23 C24 120.0(3) . . ?
C22 C23 H18 120.0 . . ?
C24 C23 H18 120.0 . . ?
C23 C24 C19 121.2(3) . . ?
C23 C24 H17 119.4 . . ?
C19 C24 H17 119.4 . . ?
C5 C25 C26 121.9(3) . . ?
C5 C25 H22 119.1 . . ?
C26 C25 H22 119.1 . . ?
C2 C26 C25 120.1(3) . . ?
C2 C26 H23 119.9 . . ?
C25 C26 H23 119.9 . . ?

_refine_diff_density_max         0.711
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.068

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_mo_190421lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1943158'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2021-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H23 F O4'
_chemical_formula_weight         418.44

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.5645(11)
_cell_length_b                   7.0521(3)
_cell_length_c                   22.8442(10)
_cell_angle_alpha                90
_cell_angle_beta                 114.5740(10)
_cell_angle_gamma                90
_cell_volume                     4038.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      3.0007
_cell_measurement_theta_max      26.4066

_exptl_crystal_description       lump
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7264
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            34057
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.625
_diffrn_reflns_theta_max         26.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4175
_reflns_number_gt                3630
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.0411P)²+3.5893P] 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         4175
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0881
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_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
F1 F 0.58968(4) 1.24688(14) 0.31353(5) 0.0414(2) Uani 1 1 d . . . . .
O1 O 0.15126(3) 1.01844(12) 0.25401(4) 0.01789(19) Uani 1 1 d . . . . .
O2 O 0.46720(3) 1.19676(12) 0.42351(4) 0.0204(2) Uani 1 1 d . . . . .
O3 O 0.48947(3) 0.64883(13) 0.36972(4) 0.0206(2) Uani 1 1 d . . . . .
O4 O 0.19713(3) 1.29042(12) 0.33423(4) 0.01852(19) Uani 1 1 d . . . . .
C1 C 0.57309(5) 0.9180(2) 0.31301(6) 0.0280(3) Uani 1 1 d . . . . .
H1 H 0.5970 0.8940 0.2936 0.034 Uiso 1 1 calc R U . . .
C2 C 0.56352(5) 1.1010(2) 0.32692(6) 0.0280(3) Uani 1 1 d . . . . .
C3 C 0.52862(5) 1.1429(2) 0.35363(6) 0.0239(3) Uani 1 1 d . . . . .
H14 H 0.5234 1.2704 0.3631 0.029 Uiso 1 1 calc R U . . .
C4 C 0.50068(5) 0.99445(19) 0.36680(6) 0.0187(3) Uani 1 1 d . . . . .
C5 C 0.46014(5) 1.05310(17) 0.39111(5) 0.0162(2) Uani 1 1 d . . . . .
C6 C 0.40987(4) 0.93677(17) 0.37130(5) 0.0147(2) Uani 1 1 d . . . . .
H15 H 0.3891 0.9300 0.3236 0.018 Uiso 1 1 calc R U . . .
C7 C 0.37490(4) 0.99042(17) 0.40750(5) 0.0145(2) Uani 1 1 d . . . . .
H16 H 0.3861 1.1151 0.4300 0.017 Uiso 1 1 calc R U . . .
C8 C 0.31541(4) 0.98536(17) 0.36686(5) 0.0150(2) Uani 1 1 d . . . . .
C9 C 0.29049(5) 0.84381(18) 0.32245(6) 0.0184(3) Uani 1 1 d . . . . .
H21 H 0.3111 0.7417 0.3178 0.022 Uiso 1 1 calc R U . . .
C10 C 0.23550(5) 0.84883(18) 0.28437(6) 0.0178(3) Uani 1 1 d . . . . .
H22 H 0.2190 0.7494 0.2546 0.021 Uiso 1 1 calc R U . . .
C11 C 0.20502(4) 0.99791(17) 0.28983(5) 0.0152(2) Uani 1 1 d . . . . .
C12 C 0.12513(5) 0.86494(18) 0.21197(6) 0.0189(3) Uani 1 1 d . . . . .
H23 H 0.1390 0.8529 0.1790 0.028 Uiso 1 1 calc R U . . .
H2 H 0.0867 0.8895 0.1912 0.028 Uiso 1 1 calc R U . . .
H3 H 0.1317 0.7471 0.2368 0.028 Uiso 1 1 calc R U . . .
C13 C 0.54726(5) 0.7704(2) 0.32784(6) 0.0240(3) Uani 1 1 d . . . . .
H13 H 0.5541 0.6434 0.3196 0.029 Uiso 1 1 calc R U . . .
C14 C 0.51105(5) 0.80700(19) 0.35485(6) 0.0192(3) Uani 1 1 d . . . . .
C15 C 0.47661(5) 0.66317(18) 0.42475(6) 0.0175(3) Uani 1 1 d . . . . .
H4 H 0.5022 0.7492 0.4572 0.021 Uiso 1 1 calc R U . . .
H12 H 0.4795 0.5367 0.4447 0.021 Uiso 1 1 calc R U . . .
C16 C 0.42072(5) 0.73851(17) 0.40409(6) 0.0154(2) Uani 1 1 d . . . . .
H5 H 0.3942 0.6441 0.3760 0.018 Uiso 1 1 calc R U . . .
C17 C 0.40233(4) 0.82043(17) 0.45455(5) 0.0150(2) Uani 1 1 d . . . . .
H11 H 0.4346 0.8717 0.4910 0.018 Uiso 1 1 calc R U . . .
C18 C 0.37365(4) 0.69469(17) 0.48282(5) 0.0157(2) Uani 1 1 d . . . . .
C19 C 0.38586(5) 0.50178(18) 0.49157(6) 0.0181(3) Uani 1 1 d . . . . .
H10 H 0.4089 0.4482 0.4746 0.022 Uiso 1 1 calc R U . . .
C20 C 0.36488(5) 0.38677(19) 0.52469(6) 0.0216(3) Uani 1 1 d . . . . .
H9 H 0.3740 0.2561 0.5307 0.026 Uiso 1 1 calc R U . . .
C21 C 0.33063(5) 0.4626(2) 0.54891(6) 0.0241(3) Uani 1 1 d . . . . .
H8 H 0.3167 0.3849 0.5723 0.029 Uiso 1 1 calc R U . . .
C22 C 0.31678(5) 0.6529(2) 0.53878(6) 0.0243(3) Uani 1 1 d . . . . .
H7 H 0.2925 0.7044 0.5542 0.029 Uiso 1 1 calc R U . . .
C23 C 0.33813(5) 0.76857(19) 0.50627(6) 0.0205(3) Uani 1 1 d . . . . .
H6 H 0.3285 0.8988 0.4999 0.025 Uiso 1 1 calc R U . . .
C24 C 0.28422(4) 1.13609(17) 0.37211(5) 0.0147(2) Uani 1 1 d . . . . .
H20 H 0.3007 1.2341 0.4025 0.018 Uiso 1 1 calc R U . . .
C25 C 0.22981(4) 1.14470(17) 0.33381(5) 0.0146(2) Uani 1 1 d . . . . .
C26 C 0.22152(5) 1.44516(19) 0.37649(7) 0.0267(3) Uani 1 1 d . . . . .
H19 H 0.2371 1.3999 0.4211 0.040 Uiso 1 1 calc R U . . .
H17 H 0.1946 1.5422 0.3714 0.040 Uiso 1 1 calc R U . . .
H18 H 0.2496 1.4998 0.3660 0.040 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
F1 C2 1.3620(16) . ?
O1 C11 1.3704(13) . ?
O1 C12 1.4275(14) . ?
O2 C5 1.2216(15) . ?
O3 C14 1.3717(16) . ?
O3 C15 1.4445(14) . ?
O4 C25 1.3693(14) . ?
O4 C26 1.4265(15) . ?
C1 C13 1.380(2) . ?
C1 C2 1.381(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.3688(19) . ?
C3 C4 1.4043(18) . ?
C3 H14 0.9500 . ?
C4 C14 1.4030(19) . ?
C4 C5 1.4980(17) . ?
C5 C6 1.5088(16) . ?
C6 C7 1.5553(15) . ?
C6 C16 1.5553(16) . ?
C6 H15 1.0000 . ?
C7 C8 1.5118(15) . ?
C7 C17 1.5774(16) . ?
C7 H16 1.0000 . ?
C8 C9 1.3848(17) . ?
C8 C24 1.4033(16) . ?
C9 C10 1.3998(16) . ?
C9 H21 0.9500 . ?
C10 C11 1.3833(17) . ?
C10 H22 0.9500 . ?
C11 C25 1.4060(17) . ?
C12 H23 0.9800 . ?
C12 H2 0.9800 . ?
C12 H3 0.9800 . ?
C13 C14 1.3985(17) . ?
C13 H13 0.9500 . ?
C15 C16 1.5079(16) . ?
C15 H4 0.9900 . ?
C15 H12 0.9900 . ?
C16 C17 1.5508(16) . ?
C16 H5 1.0000 . ?
C17 C18 1.5011(16) . ?
C17 H11 1.0000 . ?
C18 C19 1.3957(18) . ?
C18 C23 1.3977(17) . ?
C19 C20 1.3888(18) . ?
C19 H10 0.9500 . ?
C20 C21 1.3846(19) . ?
C20 H9 0.9500 . ?
C21 C22 1.388(2) . ?
C21 H8 0.9500 . ?
C22 C23 1.3880(18) . ?
C22 H7 0.9500 . ?
C23 H6 0.9500 . ?
C24 C25 1.3882(16) . ?
C24 H20 0.9500 . ?
C26 H19 0.9800 . ?
C26 H17 0.9800 . ?
C26 H18 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 116.07(9) . . ?
C14 O3 C15 116.56(10) . . ?
C25 O4 C26 116.91(9) . . ?
C13 C1 C2 118.74(12) . . ?
C13 C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
F1 C2 C3 118.23(14) . . ?
F1 C2 C1 119.00(12) . . ?
C3 C2 C1 122.77(13) . . ?
C2 C3 C4 118.98(14) . . ?
C2 C3 H14 120.5 . . ?
C4 C3 H14 120.5 . . ?
C14 C4 C3 119.10(11) . . ?
C14 C4 C5 125.17(11) . . ?
C3 C4 C5 115.70(12) . . ?
O2 C5 C4 119.88(11) . . ?
O2 C5 C6 121.85(11) . . ?
C4 C5 C6 118.18(10) . . ?
C5 C6 C7 113.78(10) . . ?
C5 C6 C16 112.06(9) . . ?
C7 C6 C16 90.01(9) . . ?
C5 C6 H15 113.0 . . ?
C7 C6 H15 113.0 . . ?
C16 C6 H15 113.0 . . ?
C8 C7 C6 114.93(9) . . ?
C8 C7 C17 119.38(10) . . ?
C6 C7 C17 87.13(8) . . ?
C8 C7 H16 111.1 . . ?
C6 C7 H16 111.1 . . ?
C17 C7 H16 111.1 . . ?
C9 C8 C24 118.28(10) . . ?
C9 C8 C7 123.21(11) . . ?
C24 C8 C7 118.44(10) . . ?
C8 C9 C10 121.07(11) . . ?
C8 C9 H21 119.5 . . ?
C10 C9 H21 119.5 . . ?
C11 C10 C9 120.30(11) . . ?
C11 C10 H22 119.9 . . ?
C9 C10 H22 119.9 . . ?
O1 C11 C10 124.95(11) . . ?
O1 C11 C25 115.62(10) . . ?
C10 C11 C25 119.41(10) . . ?
O1 C12 H23 109.5 . . ?
O1 C12 H2 109.5 . . ?
H23 C12 H2 109.5 . . ?
O1 C12 H3 109.5 . . ?
H23 C12 H3 109.5 . . ?
H2 C12 H3 109.5 . . ?
C1 C13 C14 120.34(13) . . ?
C1 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
O3 C14 C13 114.96(12) . . ?
O3 C14 C4 125.00(11) . . ?
C13 C14 C4 120.00(12) . . ?
O3 C15 C16 109.92(9) . . ?
O3 C15 H4 109.7 . . ?
C16 C15 H4 109.7 . . ?
O3 C15 H12 109.7 . . ?
C16 C15 H12 109.7 . . ?
H4 C15 H12 108.2 . . ?
C15 C16 C17 120.39(10) . . ?
C15 C16 C6 115.75(10) . . ?
C17 C16 C6 88.07(9) . . ?
C15 C16 H5 110.3 . . ?
C17 C16 H5 110.3 . . ?
C6 C16 H5 110.3 . . ?
C18 C17 C16 119.55(10) . . ?
C18 C17 C7 123.58(9) . . ?
C16 C17 C7 89.37(8) . . ?
C18 C17 H11 107.5 . . ?
C16 C17 H11 107.5 . . ?
C7 C17 H11 107.5 . . ?
C19 C18 C23 118.30(11) . . ?
C19 C18 C17 119.91(11) . . ?
C23 C18 C17 121.54(11) . . ?
C20 C19 C18 121.13(12) . . ?
C20 C19 H10 119.4 . . ?
C18 C19 H10 119.4 . . ?
C21 C20 C19 119.98(12) . . ?
C21 C20 H9 120.0 . . ?
C19 C20 H9 120.0 . . ?
C20 C21 C22 119.51(12) . . ?
C20 C21 H8 120.2 . . ?
C22 C21 H8 120.2 . . ?
C23 C22 C21 120.60(12) . . ?
C23 C22 H7 119.7 . . ?
C21 C22 H7 119.7 . . ?
C22 C23 C18 120.42(12) . . ?
C22 C23 H6 119.8 . . ?
C18 C23 H6 119.8 . . ?
C25 C24 C8 121.27(11) . . ?
C25 C24 H20 119.4 . . ?
C8 C24 H20 119.4 . . ?
O4 C25 C24 124.74(11) . . ?
O4 C25 C11 115.59(10) . . ?
C24 C25 C11 119.65(11) . . ?
O4 C26 H19 109.5 . . ?
O4 C26 H17 109.5 . . ?
H19 C26 H17 109.5 . . ?
O4 C26 H18 109.5 . . ?
H19 C26 H18 109.5 . . ?
H17 C26 H18 109.5 . . ?

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.040

_shelxl_version_number           2014/6

