# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_cu_161209c_0m
_database_code_depnum_ccdc_archive 'CCDC 1937563'
loop_
_audit_author_name
_audit_author_address
'Guangmin Yao'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 O5'
_chemical_formula_weight         346.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   6.75620(10)
_cell_length_b                   13.4704(3)
_cell_length_c                   19.4991(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1774.59(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2811
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      64.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8892
_exptl_absorpt_correction_T_max  0.9634
_exptl_absorpt_process_details   'SADABS, Sheldrick,2008'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9568
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         67.48
_reflns_number_total             3039
_reflns_number_gt                2824
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1121P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0042(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
Flack H D (1983), Acta Cryst. A39, 876-881;
Flack  parameter = 0.0(3), 1257 Friedel pairs.
Hooft et al. (2010) and Spek (2009);
Hooft parameter = 0.1(1), 1257 Bijvoet pairs.
;
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3039
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1509
_refine_ls_wR_factor_gt          0.1489
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3491(3) 0.49457(15) 0.94658(11) 0.0326(5) Uani 1 1 d . . .
C5 C 0.4857(4) 0.41199(17) 0.96266(12) 0.0437(6) Uani 1 1 d . . .
C4 C 0.5251(4) 0.41015(17) 1.04018(12) 0.0424(6) Uani 1 1 d . . .
C3 C 0.3677(4) 0.48329(19) 1.06824(12) 0.0440(6) Uani 1 1 d . . .
H3 H 0.2616 0.4442 1.0893 0.053 Uiso 1 1 calc R . .
C2 C 0.2850(4) 0.53284(18) 1.00517(12) 0.0393(5) Uani 1 1 d . . .
H2 H 0.1966 0.5857 1.0072 0.047 Uiso 1 1 calc R . .
C6 C 0.8256(4) 0.70832(18) 0.90176(12) 0.0399(5) Uani 1 1 d . . .
C7 C 0.6472(3) 0.64831(16) 0.91950(11) 0.0347(5) Uani 1 1 d . . .
H7A H 0.5884 0.6706 0.9622 0.042 Uiso 1 1 calc R . .
H7B H 0.6796 0.5784 0.9233 0.042 Uiso 1 1 calc R . .
C8 C 0.5097(3) 0.66767(15) 0.85884(9) 0.0294(5) Uani 1 1 d . . .
C9 C 0.3533(3) 0.59382(15) 0.83768(10) 0.0301(4) Uani 1 1 d . . .
C10 C 0.2834(3) 0.51840(15) 0.87556(11) 0.0328(5) Uani 1 1 d . . .
C11 C 0.2635(3) 0.61963(17) 0.76801(12) 0.0370(5) Uani 1 1 d . . .
H11A H 0.1529 0.6643 0.7753 0.044 Uiso 1 1 calc R . .
H11B H 0.2114 0.5593 0.7477 0.044 Uiso 1 1 calc R . .
C12 C 0.4061(4) 0.66788(18) 0.71670(11) 0.0414(6) Uani 1 1 d . . .
H12A H 0.3288 0.7029 0.6824 0.050 Uiso 1 1 calc R . .
H12B H 0.4788 0.6158 0.6934 0.050 Uiso 1 1 calc R . .
C13 C 0.5555(3) 0.74089(17) 0.74816(11) 0.0391(5) Uani 1 1 d . . .
H13 H 0.6466 0.7674 0.7136 0.047 Uiso 1 1 calc R . .
C14 C 0.6619(3) 0.67861(16) 0.80070(11) 0.0347(5) Uani 1 1 d . . .
H14 H 0.7002 0.6139 0.7819 0.042 Uiso 1 1 calc R . .
C15 C 0.4169(3) 0.77411(16) 0.86103(11) 0.0327(5) Uani 1 1 d . . .
H15A H 0.2754 0.7698 0.8689 0.039 Uiso 1 1 calc R . .
H15B H 0.4755 0.8125 0.8979 0.039 Uiso 1 1 calc R . .
C16 C 0.4587(4) 0.82458(15) 0.79086(11) 0.0376(5) Uani 1 1 d . . .
C17 C 0.2787(5) 0.8716(2) 0.75727(15) 0.0519(7) Uani 1 1 d . . .
H17A H 0.2377 0.9284 0.7835 0.078 Uiso 1 1 calc R . .
H17B H 0.1728 0.8242 0.7556 0.078 Uiso 1 1 calc R . .
H17C H 0.3118 0.8920 0.7115 0.078 Uiso 1 1 calc R . .
C18 C 0.7343(5) 0.4463(3) 1.05224(18) 0.0664(9) Uani 1 1 d . . .
H18A H 0.7650 0.4418 1.1002 0.100 Uiso 1 1 calc R . .
H18B H 0.7455 0.5141 1.0376 0.100 Uiso 1 1 calc R . .
H18C H 0.8250 0.4059 1.0266 0.100 Uiso 1 1 calc R . .
C19 C 0.4982(7) 0.3049(2) 1.06765(16) 0.0707(9) Uani 1 1 d . . .
H19A H 0.5884 0.2610 1.0447 0.106 Uiso 1 1 calc R . .
H19B H 0.3647 0.2835 1.0595 0.106 Uiso 1 1 calc R . .
H19C H 0.5244 0.3041 1.1160 0.106 Uiso 1 1 calc R . .
C20 C 0.1198(4) 0.4503(2) 0.85163(14) 0.0494(6) Uani 1 1 d . . .
H20A H -0.0061 0.4807 0.8606 0.074 Uiso 1 1 calc R . .
H20B H 0.1283 0.3883 0.8757 0.074 Uiso 1 1 calc R . .
H20C H 0.1333 0.4387 0.8033 0.074 Uiso 1 1 calc R . .
O1 O 0.4366(4) 0.55198(18) 1.11768(11) 0.0659(7) Uani 1 1 d . . .
O2 O 0.5568(4) 0.35495(18) 0.92188(11) 0.0835(9) Uani 1 1 d . . .
O3 O 0.9544(3) 0.73953(17) 0.93885(10) 0.0585(5) Uani 1 1 d . . .
O4 O 0.8299(2) 0.72842(13) 0.83363(8) 0.0427(4) Uani 1 1 d . . .
O5 O 0.5951(3) 0.90577(14) 0.79965(10) 0.0555(5) Uani 1 1 d . . .
H1 H 0.510(7) 0.587(3) 1.102(2) 0.083 Uiso 1 1 d . . .
H5A H 0.719(6) 0.895(3) 0.813(2) 0.083 Uiso 1 1 d . . .


_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
C1 C2 1.326(3) . ?
C1 C5 1.479(3) . ?
C1 C10 1.489(3) . ?
C5 O2 1.205(3) . ?
C5 C4 1.535(3) . ?
C4 C18 1.513(4) . ?
C4 C19 1.526(3) . ?
C4 C3 1.549(3) . ?
C3 O1 1.415(3) . ?
C3 C2 1.507(3) . ?
C3 H3 0.9800 . ?
C2 H2 0.9300 . ?
C6 O3 1.207(3) . ?
C6 O4 1.356(3) . ?
C6 C7 1.492(3) . ?
C7 C8 1.527(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.509(3) . ?
C8 C14 1.538(3) . ?
C8 C15 1.566(3) . ?
C9 C10 1.342(3) . ?
C9 C11 1.528(3) . ?
C10 C20 1.510(3) . ?
C11 C12 1.533(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.537(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.507(3) . ?
C13 C16 1.546(3) . ?
C13 H13 0.9800 . ?
C14 O4 1.466(3) . ?
C14 H14 0.9800 . ?
C15 C16 1.554(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O5 1.441(3) . ?
C16 C17 1.520(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O1 H1 0.75(4) . ?
O5 H5A 0.89(4) . ?

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 C1 C5 108.3(2) . . ?
C2 C1 C10 128.3(2) . . ?
C5 C1 C10 123.04(19) . . ?
O2 C5 C1 126.0(2) . . ?
O2 C5 C4 124.8(2) . . ?
C1 C5 C4 109.21(18) . . ?
C18 C4 C19 110.8(3) . . ?
C18 C4 C5 108.0(2) . . ?
C19 C4 C5 109.9(2) . . ?
C18 C4 C3 112.4(2) . . ?
C19 C4 C3 112.6(2) . . ?
C5 C4 C3 102.62(19) . . ?
O1 C3 C2 112.9(2) . . ?
O1 C3 C4 115.5(2) . . ?
C2 C3 C4 104.36(18) . . ?
O1 C3 H3 107.9 . . ?
C2 C3 H3 107.9 . . ?
C4 C3 H3 107.9 . . ?
C1 C2 C3 114.2(2) . . ?
C1 C2 H2 122.9 . . ?
C3 C2 H2 122.9 . . ?
O3 C6 O4 120.1(2) . . ?
O3 C6 C7 129.2(2) . . ?
O4 C6 C7 110.64(18) . . ?
C6 C7 C8 102.68(17) . . ?
C6 C7 H7A 111.2 . . ?
C8 C7 H7A 111.2 . . ?
C6 C7 H7B 111.2 . . ?
C8 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?
C9 C8 C7 121.71(17) . . ?
C9 C8 C14 109.27(16) . . ?
C7 C8 C14 100.39(17) . . ?
C9 C8 C15 109.31(17) . . ?
C7 C8 C15 112.29(16) . . ?
C14 C8 C15 101.56(16) . . ?
C10 C9 C8 126.51(18) . . ?
C10 C9 C11 121.47(19) . . ?
C8 C9 C11 111.79(17) . . ?
C9 C10 C1 124.77(19) . . ?
C9 C10 C20 123.2(2) . . ?
C1 C10 C20 111.99(19) . . ?
C9 C11 C12 115.28(19) . . ?
C9 C11 H11A 108.5 . . ?
C12 C11 H11A 108.5 . . ?
C9 C11 H11B 108.5 . . ?
C12 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 C13 115.05(18) . . ?
C11 C12 H12A 108.5 . . ?
C13 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
C13 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C12 103.21(19) . . ?
C14 C13 C16 103.99(17) . . ?
C12 C13 C16 113.80(19) . . ?
C14 C13 H13 111.8 . . ?
C12 C13 H13 111.8 . . ?
C16 C13 H13 111.8 . . ?
O4 C14 C13 114.34(18) . . ?
O4 C14 C8 103.80(16) . . ?
C13 C14 C8 103.61(17) . . ?
O4 C14 H14 111.5 . . ?
C13 C14 H14 111.5 . . ?
C8 C14 H14 111.5 . . ?
C16 C15 C8 107.69(16) . . ?
C16 C15 H15A 110.2 . . ?
C8 C15 H15A 110.2 . . ?
C16 C15 H15B 110.2 . . ?
C8 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
O5 C16 C17 104.29(19) . . ?
O5 C16 C13 110.29(19) . . ?
C17 C16 C13 114.2(2) . . ?
O5 C16 C15 110.11(18) . . ?
C17 C16 C15 114.6(2) . . ?
C13 C16 C15 103.42(16) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 O1 H1 110(3) . . ?
C6 O4 C14 108.74(17) . . ?
C16 O5 H5A 121(3) . . ?

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
C2 C1 C5 O2 172.7(3) . . . . ?
C10 C1 C5 O2 -0.9(4) . . . . ?
C2 C1 C5 C4 -7.7(3) . . . . ?
C10 C1 C5 C4 178.8(2) . . . . ?
O2 C5 C4 C18 72.0(4) . . . . ?
C1 C5 C4 C18 -107.6(2) . . . . ?
O2 C5 C4 C19 -49.0(4) . . . . ?
C1 C5 C4 C19 131.3(3) . . . . ?
O2 C5 C4 C3 -169.0(3) . . . . ?
C1 C5 C4 C3 11.3(3) . . . . ?
C18 C4 C3 O1 -19.2(3) . . . . ?
C19 C4 C3 O1 106.9(3) . . . . ?
C5 C4 C3 O1 -135.0(2) . . . . ?
C18 C4 C3 C2 105.3(3) . . . . ?
C19 C4 C3 C2 -128.6(3) . . . . ?
C5 C4 C3 C2 -10.5(3) . . . . ?
C5 C1 C2 C3 0.3(3) . . . . ?
C10 C1 C2 C3 173.4(2) . . . . ?
O1 C3 C2 C1 133.1(2) . . . . ?
C4 C3 C2 C1 6.9(3) . . . . ?
O3 C6 C7 C8 158.8(3) . . . . ?
O4 C6 C7 C8 -20.1(2) . . . . ?
C6 C7 C8 C9 153.73(18) . . . . ?
C6 C7 C8 C14 33.2(2) . . . . ?
C6 C7 C8 C15 -74.0(2) . . . . ?
C7 C8 C9 C10 16.8(3) . . . . ?
C14 C8 C9 C10 133.0(2) . . . . ?
C15 C8 C9 C10 -116.7(2) . . . . ?
C7 C8 C9 C11 -168.59(19) . . . . ?
C14 C8 C9 C11 -52.4(2) . . . . ?
C15 C8 C9 C11 57.9(2) . . . . ?
C8 C9 C10 C1 0.3(4) . . . . ?
C11 C9 C10 C1 -173.8(2) . . . . ?
C8 C9 C10 C20 177.2(2) . . . . ?
C11 C9 C10 C20 3.2(3) . . . . ?
C2 C1 C10 C9 84.8(3) . . . . ?
C5 C1 C10 C9 -103.1(3) . . . . ?
C2 C1 C10 C20 -92.5(3) . . . . ?
C5 C1 C10 C20 79.7(3) . . . . ?
C10 C9 C11 C12 -151.6(2) . . . . ?
C8 C9 C11 C12 33.6(3) . . . . ?
C9 C11 C12 C13 -37.4(3) . . . . ?
C11 C12 C13 C14 57.3(2) . . . . ?
C11 C12 C13 C16 -54.7(3) . . . . ?
C12 C13 C14 O4 173.68(17) . . . . ?
C16 C13 C14 O4 -67.3(2) . . . . ?
C12 C13 C14 C8 -74.1(2) . . . . ?
C16 C13 C14 C8 45.0(2) . . . . ?
C9 C8 C14 O4 -164.82(16) . . . . ?
C7 C8 C14 O4 -35.8(2) . . . . ?
C15 C8 C14 O4 79.78(19) . . . . ?
C9 C8 C14 C13 75.4(2) . . . . ?
C7 C8 C14 C13 -155.50(17) . . . . ?
C15 C8 C14 C13 -40.0(2) . . . . ?
C9 C8 C15 C16 -94.76(19) . . . . ?
C7 C8 C15 C16 127.0(2) . . . . ?
C14 C8 C15 C16 20.6(2) . . . . ?
C14 C13 C16 O5 87.0(2) . . . . ?
C12 C13 C16 O5 -161.44(19) . . . . ?
C14 C13 C16 C17 -155.9(2) . . . . ?
C12 C13 C16 C17 -44.4(3) . . . . ?
C14 C13 C16 C15 -30.7(2) . . . . ?
C12 C13 C16 C15 80.8(2) . . . . ?
C8 C15 C16 O5 -112.2(2) . . . . ?
C8 C15 C16 C17 130.6(2) . . . . ?
C8 C15 C16 C13 5.7(2) . . . . ?
O3 C6 O4 C14 177.7(2) . . . . ?
C7 C6 O4 C14 -3.3(3) . . . . ?
C13 C14 O4 C6 137.36(19) . . . . ?
C8 C14 O4 C6 25.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        67.48
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_cu_170425f_0m
_database_code_depnum_ccdc_archive 'CCDC 1937564'
loop_
_audit_author_name
_audit_author_address
'Guangmin Yao'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 O4'
_chemical_formula_weight         328.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.2254(4)
_cell_length_b                   6.4604(3)
_cell_length_c                   12.6646(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.606(2)
_cell_angle_gamma                90
_cell_volume                     875.42(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4819
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      57.40

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.692
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6731
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.661
_diffrn_reflns_theta_max         58.003
_diffrn_reflns_theta_full        58.003
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             2352
_reflns_number_gt                2277
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_max     0.938
_reflns_Friedel_fraction_full    0.938

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0433P)²+0.1001P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 983 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.14(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2352
_refine_ls_number_parameters     222
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0795
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
C1 C 0.0701(2) 0.6384(4) 0.34294(18) 0.0436(6) Uani 1 1 d . . . . .
C2 C -0.0110(2) 0.4815(4) 0.3212(2) 0.0497(6) Uani 1 1 d . . . . .
H2 H 0.0120 0.3464 0.3109 0.060 Uiso 1 1 calc R U . . .
C3 C -0.1414(2) 0.5404(4) 0.3146(2) 0.0471(6) Uani 1 1 d . . . . .
H3 H -0.1541 0.5031 0.3854 0.057 Uiso 1 1 calc R U . . .
C4 C -0.1403(2) 0.7788(4) 0.3084(2) 0.0502(6) Uani 1 1 d . . . . .
C5 C -0.0019(3) 0.8269(4) 0.3508(2) 0.0539(7) Uani 1 1 d . . . . .
C6 C 0.1277(2) 0.6206(4) 0.1060(2) 0.0479(6) Uani 1 1 d . . . . .
H6A H 0.0650 0.5218 0.0664 0.058 Uiso 1 1 calc R U . . .
H6B H 0.0912 0.7132 0.1480 0.058 Uiso 1 1 calc R U . . .
C7 C 0.1807(2) 0.7386(5) 0.0279(2) 0.0510(7) Uani 1 1 d . . . . .
C8 C 0.2425(2) 0.5118(4) 0.18058(19) 0.0414(6) Uani 1 1 d . . . . .
C9 C 0.2520(2) 0.4566(4) 0.3016(2) 0.0491(6) Uani 1 1 d . . . . .
H9 H 0.1960 0.3388 0.2984 0.059 Uiso 1 1 calc R U . . .
C10 C 0.2057(2) 0.6310(5) 0.3596(2) 0.0516(7) Uani 1 1 d . . . . .
C11 C 0.3870(3) 0.3775(6) 0.3589(3) 0.0716(9) Uani 1 1 d . . . . .
H11A H 0.4043 0.3944 0.4382 0.086 Uiso 1 1 calc R U . . .
H11B H 0.3889 0.2303 0.3445 0.086 Uiso 1 1 calc R U . . .
C12 C 0.4941(3) 0.4806(7) 0.3253(3) 0.0718(9) Uani 1 1 d . . . . .
H12A H 0.5175 0.6086 0.3664 0.086 Uiso 1 1 calc R U . . .
H12B H 0.5664 0.3898 0.3454 0.086 Uiso 1 1 calc R U . . .
C13 C 0.4584(2) 0.5275(5) 0.2009(2) 0.0538(7) Uani 1 1 d . . . . .
H13 H 0.5267 0.5899 0.1787 0.065 Uiso 1 1 calc R U . . .
C14 C 0.3458(2) 0.6667(4) 0.1800(2) 0.0454(6) Uani 1 1 d . . . . .
H14 H 0.3568 0.7719 0.2380 0.054 Uiso 1 1 calc R U . . .
C15 C 0.2827(2) 0.3287(4) 0.1252(2) 0.0497(6) Uani 1 1 d . . . . .
H15 H 0.2295 0.2233 0.0891 0.060 Uiso 1 1 calc R U . . .
C16 C 0.4048(2) 0.3374(4) 0.1348(2) 0.0529(7) Uani 1 1 d . . . . .
C17 C 0.4832(3) 0.1880(6) 0.0972(3) 0.0769(10) Uani 1 1 d . . . . .
H17A H 0.4310 0.0833 0.0524 0.115 Uiso 1 1 calc R U . . .
H17B H 0.5417 0.1246 0.1604 0.115 Uiso 1 1 calc R U . . .
H17C H 0.5279 0.2591 0.0543 0.115 Uiso 1 1 calc R U . . .
C18 C -0.2126(3) 0.8840(6) 0.3778(3) 0.0788(10) Uani 1 1 d . . . . .
H18A H -0.1824 0.8351 0.4528 0.118 Uiso 1 1 calc R U . . .
H18B H -0.2999 0.8521 0.3478 0.118 Uiso 1 1 calc R U . . .
H18C H -0.2010 1.0311 0.3766 0.118 Uiso 1 1 calc R U . . .
C19 C -0.1874(3) 0.8535(6) 0.1889(3) 0.0727(9) Uani 1 1 d . . . . .
H19A H -0.1747 1.0002 0.1866 0.109 Uiso 1 1 calc R U . . .
H19B H -0.2749 0.8230 0.1590 0.109 Uiso 1 1 calc R U . . .
H19C H -0.1422 0.7844 0.1458 0.109 Uiso 1 1 calc R U . . .
C20 C 0.2807(3) 0.7724(7) 0.4219(3) 0.0787(10) Uani 1 1 d . . . . .
H20A H 0.2475 0.8766 0.4553 0.094 Uiso 1 1 calc R U . . .
H20B H 0.3662 0.7672 0.4322 0.094 Uiso 1 1 calc R U . . .
O1 O -0.23408(17) 0.4385(3) 0.23065(19) 0.0642(6) Uani 1 1 d . . . . .
H1 H -0.2132 0.4348 0.1740 0.096 Uiso 1 1 calc R U . . .
O2 O 0.0405(2) 0.9944(4) 0.3862(3) 0.0956(9) Uani 1 1 d . . . . .
O3 O 0.1249(2) 0.8148(4) -0.06004(17) 0.0754(7) Uani 1 1 d . . . . .
O4 O 0.30446(17) 0.7566(3) 0.06994(15) 0.0537(5) Uani 1 1 d . . . . .


_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
C1 C2 1.334(4) . ?
C1 C10 1.474(4) . ?
C1 C5 1.481(4) . ?
C2 C3 1.491(4) . ?
C2 H2 0.9300 . ?
C3 O1 1.406(3) . ?
C3 C4 1.542(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.515(4) . ?
C4 C19 1.522(4) . ?
C4 C18 1.525(4) . ?
C5 O2 1.212(4) . ?
C6 C7 1.506(4) . ?
C6 C8 1.520(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O3 1.206(3) . ?
C7 O4 1.334(3) . ?
C8 C15 1.512(4) . ?
C8 C14 1.534(3) . ?
C8 C9 1.546(3) . ?
C9 C10 1.519(4) . ?
C9 C11 1.555(4) . ?
C9 H9 0.9800 . ?
C10 C20 1.328(4) . ?
C11 C12 1.543(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.534(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C16 1.506(4) . ?
C13 C14 1.508(4) . ?
C13 H13 0.9800 . ?
C14 O4 1.451(3) . ?
C14 H14 0.9800 . ?
C15 C16 1.339(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.479(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9300 . ?
C20 H20B 0.9300 . ?
O1 H1 0.8200 . ?

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 C1 C10 128.0(3) . . ?
C2 C1 C5 106.7(2) . . ?
C10 C1 C5 125.3(2) . . ?
C1 C2 C3 114.5(2) . . ?
C1 C2 H2 122.8 . . ?
C3 C2 H2 122.8 . . ?
O1 C3 C2 114.3(2) . . ?
O1 C3 C4 116.4(2) . . ?
C2 C3 C4 103.6(2) . . ?
O1 C3 H3 107.3 . . ?
C2 C3 H3 107.3 . . ?
C4 C3 H3 107.3 . . ?
C5 C4 C19 107.3(2) . . ?
C5 C4 C18 111.8(2) . . ?
C19 C4 C18 110.3(3) . . ?
C5 C4 C3 102.1(2) . . ?
C19 C4 C3 111.2(2) . . ?
C18 C4 C3 113.7(3) . . ?
O2 C5 C1 126.7(3) . . ?
O2 C5 C4 124.1(3) . . ?
C1 C5 C4 109.2(2) . . ?
C7 C6 C8 102.32(19) . . ?
C7 C6 H6A 111.3 . . ?
C8 C6 H6A 111.3 . . ?
C7 C6 H6B 111.3 . . ?
C8 C6 H6B 111.3 . . ?
H6A C6 H6B 109.2 . . ?
O3 C7 O4 121.3(2) . . ?
O3 C7 C6 128.0(2) . . ?
O4 C7 C6 110.7(2) . . ?
C15 C8 C6 112.9(2) . . ?
C15 C8 C14 100.12(19) . . ?
C6 C8 C14 101.3(2) . . ?
C15 C8 C9 109.8(2) . . ?
C6 C8 C9 121.0(2) . . ?
C14 C8 C9 109.22(19) . . ?
C10 C9 C8 112.1(2) . . ?
C10 C9 C11 116.5(2) . . ?
C8 C9 C11 107.7(2) . . ?
C10 C9 H9 106.7 . . ?
C8 C9 H9 106.7 . . ?
C11 C9 H9 106.7 . . ?
C20 C10 C1 120.2(3) . . ?
C20 C10 C9 123.3(2) . . ?
C1 C10 C9 116.4(2) . . ?
C12 C11 C9 117.4(3) . . ?
C12 C11 H11A 107.9 . . ?
C9 C11 H11A 107.9 . . ?
C12 C11 H11B 107.9 . . ?
C9 C11 H11B 107.9 . . ?
H11A C11 H11B 107.2 . . ?
C13 C12 C11 112.6(2) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C16 C13 C14 102.5(2) . . ?
C16 C13 C12 110.2(3) . . ?
C14 C13 C12 104.1(2) . . ?
C16 C13 H13 113.1 . . ?
C14 C13 H13 113.1 . . ?
C12 C13 H13 113.1 . . ?
O4 C14 C13 114.5(2) . . ?
O4 C14 C8 104.06(18) . . ?
C13 C14 C8 101.8(2) . . ?
O4 C14 H14 111.9 . . ?
C13 C14 H14 111.9 . . ?
C8 C14 H14 111.9 . . ?
C16 C15 C8 111.5(2) . . ?
C16 C15 H15 124.3 . . ?
C8 C15 H15 124.3 . . ?
C15 C16 C17 129.5(3) . . ?
C15 C16 C13 108.1(2) . . ?
C17 C16 C13 122.3(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 120.0 . . ?
C10 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
C3 O1 H1 109.5 . . ?
C7 O4 C14 109.89(18) . . ?

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
C10 C1 C2 C3 177.1(2) . . . . ?
C5 C1 C2 C3 -1.4(3) . . . . ?
C1 C2 C3 O1 140.9(2) . . . . ?
C1 C2 C3 C4 13.2(3) . . . . ?
O1 C3 C4 C5 -144.8(2) . . . . ?
C2 C3 C4 C5 -18.4(3) . . . . ?
O1 C3 C4 C19 -30.6(3) . . . . ?
C2 C3 C4 C19 95.8(3) . . . . ?
O1 C3 C4 C18 94.6(3) . . . . ?
C2 C3 C4 C18 -139.0(2) . . . . ?
C2 C1 C5 O2 167.6(3) . . . . ?
C10 C1 C5 O2 -10.9(5) . . . . ?
C2 C1 C5 C4 -11.6(3) . . . . ?
C10 C1 C5 C4 169.9(2) . . . . ?
C19 C4 C5 O2 82.6(4) . . . . ?
C18 C4 C5 O2 -38.5(4) . . . . ?
C3 C4 C5 O2 -160.4(3) . . . . ?
C19 C4 C5 C1 -98.2(3) . . . . ?
C18 C4 C5 C1 140.8(3) . . . . ?
C3 C4 C5 C1 18.8(3) . . . . ?
C8 C6 C7 O3 163.3(3) . . . . ?
C8 C6 C7 O4 -18.3(3) . . . . ?
C7 C6 C8 C15 -75.6(3) . . . . ?
C7 C6 C8 C14 30.6(3) . . . . ?
C7 C6 C8 C9 151.4(2) . . . . ?
C15 C8 C9 C10 -176.8(2) . . . . ?
C6 C8 C9 C10 -42.5(3) . . . . ?
C14 C8 C9 C10 74.3(3) . . . . ?
C15 C8 C9 C11 53.8(3) . . . . ?
C6 C8 C9 C11 -171.9(3) . . . . ?
C14 C8 C9 C11 -55.1(3) . . . . ?
C2 C1 C10 C20 -152.7(3) . . . . ?
C5 C1 C10 C20 25.4(4) . . . . ?
C2 C1 C10 C9 27.6(4) . . . . ?
C5 C1 C10 C9 -154.2(2) . . . . ?
C8 C9 C10 C20 -94.9(3) . . . . ?
C11 C9 C10 C20 29.8(4) . . . . ?
C8 C9 C10 C1 84.8(3) . . . . ?
C11 C9 C10 C1 -150.5(2) . . . . ?
C10 C9 C11 C12 -91.2(3) . . . . ?
C8 C9 C11 C12 35.7(4) . . . . ?
C9 C11 C12 C13 -39.0(5) . . . . ?
C11 C12 C13 C16 -50.9(4) . . . . ?
C11 C12 C13 C14 58.3(4) . . . . ?
C16 C13 C14 O4 -73.3(3) . . . . ?
C12 C13 C14 O4 171.8(2) . . . . ?
C16 C13 C14 C8 38.3(2) . . . . ?
C12 C13 C14 C8 -76.6(3) . . . . ?
C15 C8 C14 O4 82.7(2) . . . . ?
C6 C8 C14 O4 -33.4(2) . . . . ?
C9 C8 C14 O4 -162.1(2) . . . . ?
C15 C8 C14 C13 -36.6(2) . . . . ?
C6 C8 C14 C13 -152.7(2) . . . . ?
C9 C8 C14 C13 78.6(2) . . . . ?
C6 C8 C15 C16 129.5(2) . . . . ?
C14 C8 C15 C16 22.6(3) . . . . ?
C9 C8 C15 C16 -92.2(3) . . . . ?
C8 C15 C16 C17 177.4(3) . . . . ?
C8 C15 C16 C13 1.4(3) . . . . ?
C14 C13 C16 C15 -25.5(3) . . . . ?
C12 C13 C16 C15 84.8(3) . . . . ?
C14 C13 C16 C17 158.2(3) . . . . ?
C12 C13 C16 C17 -91.5(3) . . . . ?
O3 C7 O4 C14 175.1(3) . . . . ?
C6 C7 O4 C14 -3.4(3) . . . . ?
C13 C14 O4 C7 133.9(2) . . . . ?
C8 C14 O4 C7 23.7(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
O1 H1 O3 0.82 2.13 2.900(3) 156.8 2_545
C6 H6A O3 0.97 2.50 3.359(3) 148.0 2_545
C2 H2 O2 0.93 2.45 3.260(4) 145.7 1_545

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.026


